JP2023177281A - Polycyclic aromatic compounds - Google Patents

Abstract

To provide nove polycyclic aromatic compounds, and organic EL devices using the compounds.SOLUTION: Polycyclic aromatic compounds represented by general formula (1) or general formula (2) broaden options for an organic device material. Further, the novel materials are used to fabricate, e.g., organic EL devices, thereby providing superior devices.SELECTED DRAWING: None

Description

The present invention relates to a polycyclic aromatic compound, an organic electroluminescent device, an organic field effect transistor, an organic thin film solar cell, a wavelength conversion filter, a display device, and a lighting device using the same. Note that in this specification, an "organic electroluminescent device" may be referred to as an "organic EL device" or simply "device."

Conventionally, display devices using light-emitting elements that emit electroluminescence have been studied in various ways because they can save power and be made thinner.Furthermore, organic electroluminescent elements made of organic materials can be easily made lighter and larger. As a result, it has been actively considered. In particular, we are developing organic materials that emit light such as green, which is one of the three primary colors of light, and organic materials that have the ability to transport charges such as holes and electrons (which have the potential to become semiconductors and superconductors). Regarding development, research has been active so far, regardless of whether it is a high-molecular compound or a low-molecular compound.

An organic EL element has a structure consisting of a pair of electrodes consisting of an anode and a cathode, and one or more layers containing an organic compound and disposed between the pair of electrodes. Layers containing organic compounds include a light-emitting layer and a charge transport/injection layer that transports or injects charges such as holes and electrons, and various organic materials suitable for these layers have been developed.

As materials for the light-emitting layer, benzofluorene compounds, for example, have been developed (International Publication No. 2004/061047). Further, as hole transport materials, for example, triphenylamine compounds have been developed (Japanese Patent Laid-Open No. 2001-172232). Further, as electron transport materials, for example, anthracene compounds have been developed (Japanese Patent Laid-Open No. 2005-170911).

Furthermore, in recent years, materials improved from triphenylamine derivatives have been reported as materials for use in organic EL elements and organic thin film solar cells (International Publication No. 2012/118164). This material was created based on N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), which had already been put into practical use. This material is characterized in that by connecting the aromatic rings that make up triphenylamine, nitrogen is placed at the center of the ring structure while increasing its planarity. In this document, for example, the charge transport properties of an NO-linked compound (compound 1 on page 63) are evaluated, but there is no description of the method for producing materials other than the NO-linked compound, and there is no description of the method for producing materials other than the NO-linked compound. Since different compounds have different electronic states as a whole, the properties that can be obtained from materials other than NO-linked compounds are still unknown. Other examples of such compounds can be found (WO 2011/107186). For example, a compound having a conjugated structure with a large triplet exciton energy (T1) can emit phosphorescence with a shorter wavelength and is therefore useful as a material for a green light-emitting layer. Furthermore, compounds having a novel conjugated structure with a large T1 are required as electron transport materials and hole transport materials that sandwich a light emitting layer.

Host materials for organic EL devices are generally molecules in which a plurality of existing aromatic rings, such as benzene and carbazole, are connected by single bonds, phosphorus atoms, and silicon atoms. This is because a large HOMO-LUMO gap (band gap Eg in a thin film) required for the host material is ensured by connecting a large number of relatively small conjugated aromatic rings. Furthermore, host materials for organic EL devices using phosphorescent materials or thermally activated delayed fluorescent materials require high triplet excitation energy ( _E By connecting SOMO1 and SOMO2 in the triplet excited state (T1), it is possible to improve the triplet excitation energy (E _T ) by reducing the exchange interaction between both orbitals. becomes. However, small aromatic rings in conjugated systems do not have sufficient redox stability, and devices using molecules that connect existing aromatic rings as host materials do not have sufficient lifespans. On the other hand, polycyclic aromatic compounds with extended π-conjugated systems generally have excellent redox stability, but their HOMO-LUMO gap (band gap Eg in thin films) and triplet excitation energy (E _T ) are low. It has been considered unsuitable as a host material.

Furthermore, in recent years, compounds in which multiple aromatic rings are condensed with boron or the like as a central atom have been reported (International Publication No. 2015/102118). In this document, an evaluation of an organic EL device using a compound in which a plurality of aromatic rings are condensed as a dopant material for a light emitting layer is performed.

International Publication No. 2004/061047 Japanese Patent Application Publication No. 2001-172232 Japanese Patent Application Publication No. 2005-170911 International Publication No. 2012/118164 International Publication No. 2011/107186 International Publication No. 2015/102118

As reported in Patent Documents 1 to 5, various materials have been developed for use in organic EL elements, but in order to increase the selection of materials for organic EL elements, materials made of compounds different from conventional ones have been developed. development is desired. In particular, it is useful to explore organic EL properties that can be obtained from materials other than NO-linked compounds in which nitrogen is placed at the center of the ring structure, and methods for producing the same.

Further, Patent Document 6 reports a polycyclic aromatic compound containing boron and an organic EL device using the same, but this document discloses an extremely large number of compounds, and further improves device characteristics. Therefore, it is useful to search for materials for the light emitting layer, especially dopant materials, that can improve organic EL characteristics such as luminous efficiency and device life.

In addition, as a method for forming organic layers constituting organic EL elements, wet film forming methods are currently used in addition to vacuum evaporation methods. The development of ink materials for wet film formation is actively underway, and it would be beneficial to explore such ink materials.

As a result of intensive studies to solve the above problems, the present inventors have found that by configuring, for example, an organic EL device by arranging a layer containing a polycyclic aromatic compound having a novel structure between a pair of electrodes, It was discovered that an excellent organic EL device could be obtained, and the present invention was completed. That is, the present invention provides a polycyclic aromatic compound as described below, and a material for organic devices such as a material for an organic EL element containing a polycyclic aromatic compound as described below.

Note that in this specification, chemical structures and substituents are sometimes expressed by the number of carbon atoms, but when a chemical structure is substituted with a substituent, or when a substituent is further substituted with a substituent, the number of carbon atoms is the same as the number of carbon atoms in the chemical structure. It means the number of carbon atoms of each substituent or substituent, and does not mean the total number of carbon atoms of the chemical structure and substituent, or the total number of carbon atoms of the substituent and substituent. For example, "substituent B having a carbon number Y substituted with a substituent A having a carbon number X" means that "substituent B having a carbon number Y" is substituted with "substituent A having a carbon number X". However, the carbon number Y is not the total carbon number of substituent A and substituent B. For example, "substituent B having carbon number Y and substituted by substituent A" means that "substituent B having carbon number Y" is substituted with "substituent A (of which the number of carbon atoms is not limited)". However, the carbon number Y is not the total carbon number of substituent A and substituent B.

上記一般式（１）および一般式（２）中、
［φ］ｎは、下記式（φ－ａ－１）～（φ－ａ－６）：

からなる群から選択される少なくとも１種の単位構造と、下記式（φ－ｂ）：

の単位構造と、
が合計でｎ個連結して構成され、この際、前記式（φ－ａ－１）～（φ－ａ－６）と前記式（φ－ｂ）とは交互に連結され、
ｎは３以上の整数であり
Ｘは、それぞれ独立して、＞Ｎ－Ｒ^１、＞Ｏ、＞Ｃ（－Ｒ^２）_２、＞Ｓｉ（－Ｒ^２）_２、＞Ｓ、または＞Ｓｅであり、
前記Ｒ^１は、水素、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のアルキル、または置換もしくは無置換のシクロアルキルであり、
前記Ｒ^２は、それぞれ独立して、水素、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のアルキル、または置換もしくは無置換のシクロアルキルであり、
この際、２つのＲ^２は互いに結合して環を形成していてもよく、
Ｒ^１またはＲ^２は、連結基または単結合により、ａ環、ｂ環、ｄ環、およびｅ環の少なくとも１つと結合して環を形成していてもよく、
Ｙは、それぞれ独立して、Ｂ、Ｐ、Ｐ＝Ｏ、Ｐ＝Ｓ、Ａｌ、Ｇａ、Ａｓ、Ｓｉ－Ｒ^３、またはＧｅ－Ｒ^３であり、
前記Ｒ^３は、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のアルキル、または置換もしくは無置換のシクロアルキルであり、
Ｚは、それぞれ独立して、－Ｃ（－Ｒ^４）＝または－Ｎ＝であり、この際、任意の「－Ｃ（－Ｒ^４）＝Ｃ（－Ｒ^４）－」は、「－Ｎ（－Ｒ^４）－」、「－Ｏ－」、「－Ｓ－」、「－Ｃ（－Ｒ^４）_２－」、「－Ｓｉ（－Ｒ^４）_２－」、または「－Ｓｅ－」に置き換わっていてもよく、前記「－Ｃ（－Ｒ^４）_２－」の２つのＲ^４同士および「－Ｓｉ（－Ｒ^４）_２－」の２つのＲ^４同士は、それぞれ独立して、単結合、－ＣＲ^５＝ＣＲ^５－、－Ｃ≡Ｃ－、－Ｎ（－Ｒ^５）－、－Ｏ－、－Ｓ－、－Ｃ（－Ｒ^５）_２－、－Ｓｉ（－Ｒ^５）_２－、－Ｃ（＝Ｏ）－または－Ｓｅ－を介して結合していてもよく、
前記Ｒ^４は、それぞれ独立して、水素、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のジアリールアミノ（２つのアリールは互いに連結基または単結合を介して結合していてもよい）、置換もしくは無置換のジヘテロアリールアミノ（２つのヘテロアリールは互いに連結基または単結合を介して結合していてもよい）、置換もしくは無置換のアリールヘテロアリールアミノ（アリールとヘテロアリールとは互いに連結基または単結合を介して結合していてもよい）、置換もしくは無置換のジアリールボリル（２つのアリールは単結合または連結基または単結合を介して結合していてもよい）、置換もしくは無置換のアルキル、置換もしくは無置換のアルコキシ、置換もしくは無置換のアリールオキシ、または置換もしくは無置換のアミノであり、
前記Ｒ^５は、それぞれ独立して、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のアルキル、または置換もしくは無置換のシクロアルキルであり、
この際、異なるｃ環の２つのＺ、ｃ環のＺおよびｄ環のＺ、ｃ環のＺおよびｅ環のＺは連結基または単結合により結合して環を形成していてもよく、
前記一般式（１）または一般式（２）における前記ａ環、ｂ環、ｃ環、ｄ環、置換もしくは無置換のアリール、および置換もしくは無置換のヘテロアリールの少なくとも１つは、少なくとも１つのシクロアルカンで縮合されていてもよく、当該シクロアルカンにおける少なくとも１つの水素は置換されていてもよく、当該シクロアルカンにおける少なくとも１つの「－ＣＨ_２－」は「－Ｏ－」で置換されていてもよく、
前記一般式（１）または一般式（２）において、少なくとも１つの水素はシアノ、ハロゲン、または重水素で置き換えられていてもよい。 [1] Polycyclic aromatic compound represented by the following general formula (1) or general formula (2):

In the above general formula (1) and general formula (2),
[φ]n is the following formula (φ-a-1) to (φ-a-6):

At least one unit structure selected from the group consisting of, and the following formula (φ-b):

The unit structure of
are configured by connecting n pieces in total, and in this case, the formulas (φ-a-1) to (φ-a-6) and the formula (φ-b) are alternately connected,
ⁿ is _an integer ^{of 3} _or more; can be,
The R ¹ is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl,
The R ² is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl,
In this case, two R ² may be bonded to each other to form a ring,
R ¹ or R ² may be bonded to at least one of ring a, ring b, ring d, and ring e through a linking group or a single bond to form a ring,
Y is each independently B, P, P=O, P=S, Al, Ga, As, Si-R ³ , or Ge-R ³ ,
The R ³ is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl,
Z is each independently -C(-R ⁴ )= or -N=, and in this case, any "-C(-R ⁴ )=C(-R ⁴ )-" is "-N (-R ⁴ )-", "-O-", "-S-", "-C(-R ⁴ ) _2- ", "-Si(-R ⁴ ) _2- ", or "-Se-" The two R ^4s in "-C(-R ⁴ ) ₂ --" and the two R ^4s in "-Si(-R ⁴ ) ₂ --" each independently represent Single bond, -CR ⁵ =CR ⁵ -, -C≡C-, -N(-R ⁵ )-, -O-, -S-, -C(-R ⁵ ) ₂ -, -Si(-R ⁵ ) ₂ -, may be bonded via -C(=O)- or -Se-,
The above R ⁴ is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino (two aryls are bonded to each other via a linking group or a single bond); ), substituted or unsubstituted diheteroarylamino (two heteroaryls may be bonded to each other via a linking group or a single bond), substituted or unsubstituted arylheteroarylamino (aryl and Heteroaryl may be bonded to each other via a linking group or a single bond), substituted or unsubstituted diarylboryl (two aryls may be bonded to each other via a single bond, a linking group, or a single bond) ), substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstituted amino,
The R ⁵ is each independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl,
In this case, two Z of different c rings, Z of the c ring and Z of the d ring, Z of the c ring and Z of the e ring may be bonded by a linking group or a single bond to form a ring,
At least one of the a-ring, b-ring, c-ring, d-ring, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl in the general formula (1) or general formula (2) has at least one It may be condensed with a cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one "-CH ₂ -" in the cycloalkane may be substituted with "-O-". Good too,
In the general formula (1) or general formula (2), at least one hydrogen may be replaced with cyano, halogen, or deuterium.

[2] X is >NR ¹ ,
Y is B,
The polycyclic aromatic compound according to the above [1], wherein Z is -C(-R ⁴ )=.

[3] The polycyclic aromatic compound according to [1] above, wherein [φ]n includes a unit structure of formula (φ-a-1) and a unit structure of formula (φ-b).

[4] [φ]n includes the unit structure of formulas (φ-a-1) to (φ-a-3) and the unit structure of formula (φ-b) as described in [1] above. Polycyclic aromatic compound.

[5] The polycyclic aromatic compound according to [1] above, wherein n is 3 to 9.

[6] The polycyclic aromatic compound according to [1] above, wherein R ⁴ is each independently hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted diphenylamino. .

[7] The polycyclic aromatic compound according to [1] above, wherein at least one of R ⁴ is alkyl having 8 to 30 carbon atoms.

上記式（φ－１）中、
Ｘは、それぞれ独立して、＞Ｎ－Ｒ^１、＞Ｏ、＞Ｃ（－Ｒ^２）_２、＞Ｓｉ（－Ｒ^２）_２、＞Ｓ、または＞Ｓｅであり、
前記Ｒ^１は、水素、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のアルキル、または置換もしくは無置換のシクロアルキルであり、
前記Ｒ^２は、それぞれ独立して、水素、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のアルキル、または置換もしくは無置換のシクロアルキルであり、
この際、２つのＲ^２は互いに結合して環を形成していてもよく、
Ｒ^１またはＲ^２は、連結基または単結合により、ａ環、ｂ環、ｄ環、およびｅ環の少なくとも１つと結合して環を形成していてもよく、
Ｙは、それぞれ独立して、Ｂ、Ｐ、Ｐ＝Ｏ、Ｐ＝Ｓ、Ａｌ、Ｇａ、Ａｓ、Ｓｉ－Ｒ^３、またはＧｅ－Ｒ^３であり、
前記Ｒ^３は、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のアルキル、または置換もしくは無置換のシクロアルキルであり、
Ｚは、それぞれ独立して、－Ｃ（－Ｒ^４）＝または－Ｎ＝であり、この際、任意の「－Ｃ（－Ｒ^４）＝Ｃ（－Ｒ^４）－」は、「－Ｎ（－Ｒ^４）－」、「－Ｏ－」、「－Ｓ－」、「－Ｃ（－Ｒ^４）_２－」、「－Ｓｉ（－Ｒ^４）_２－」、または「－Ｓｅ－」に置き換わっていてもよく、前記「－Ｃ（－Ｒ^４）_２－」の２つのＲ^４同士および「－Ｓｉ（－Ｒ^４）_２－」の２つのＲ^４同士は、それぞれ独立して、単結合、－ＣＲ^５＝ＣＲ^５－、－Ｃ≡Ｃ－、－Ｎ（－Ｒ^５）－、－Ｏ－、－Ｓ－、－Ｃ（－Ｒ^５）_２－、－Ｓｉ（－Ｒ^５）_２－、－Ｃ（＝Ｏ）－または－Ｓｅ－を介して結合していてもよく、
前記Ｒ^４は、それぞれ独立して、水素、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のジアリールアミノ（２つのアリールは互いに連結基または単結合を介して結合していてもよい）、置換もしくは無置換のジヘテロアリールアミノ（２つのヘテロアリールは互いに連結基または単結合を介して結合していてもよい）、置換もしくは無置換のアリールヘテロアリールアミノ（アリールとヘテロアリールとは互いに連結基または単結合を介して結合していてもよい）、置換もしくは無置換のジアリールボリル（２つのアリールは単結合または連結基または単結合を介して結合していてもよい）、置換もしくは無置換のアルキル、置換もしくは無置換のアルコキシ、置換もしくは無置換のアリールオキシ、または置換もしくは無置換のアミノであり、
前記Ｒ^５は、それぞれ独立して、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のアルキル、または置換もしくは無置換のシクロアルキルである。 [8] The polycyclic aromatic compound according to [1] above, wherein [φ]n includes a unit structure of the following formula (φ-1):

In the above formula (φ-1),
X is each independently >NR ¹ , >O, >C(-R ² ) ₂ , >Si(-R ² ) ₂ , >S, or >Se;
The R ¹ is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl,
The R ² is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl,
In this case, two R ² may be bonded to each other to form a ring,
R ¹ or R ² may be bonded to at least one of ring a, ring b, ring d, and ring e through a linking group or a single bond to form a ring,
Y is each independently B, P, P=O, P=S, Al, Ga, As, Si-R ³ , or Ge-R ³ ,
The R ³ is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl,
Z is each independently -C(-R ⁴ )= or -N=, and in this case, any "-C(-R ⁴ )=C(-R ⁴ )-" is "-N (-R ⁴ )-", "-O-", "-S-", "-C(-R ⁴ ) _2- ", "-Si(-R ⁴ ) _2- ", or "-Se-" The two R ^4s in "-C(-R ⁴ ) ₂ --" and the two R ^4s in "-Si(-R ⁴ ) ₂ --" each independently represent Single bond, -CR ⁵ =CR ⁵ -, -C≡C-, -N(-R ⁵ )-, -O-, -S-, -C(-R ⁵ ) ₂ -, -Si(-R ⁵ ) ₂ -, may be bonded via -C(=O)- or -Se-,
The above R ⁴ is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino (two aryls are bonded to each other via a linking group or a single bond); ), substituted or unsubstituted diheteroarylamino (two heteroaryls may be bonded to each other via a linking group or a single bond), substituted or unsubstituted arylheteroarylamino (aryl and Heteroaryl may be bonded to each other via a linking group or a single bond), substituted or unsubstituted diarylboryl (two aryls may be bonded to each other via a single bond, a linking group, or a single bond) ), substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstituted amino,
Each R ⁵ is independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl.

の単位構造を含む、上記［８］に記載の多環芳香族化合物。 [9] [φ]n is the following formula (φ-1-1):

The polycyclic aromatic compound according to the above [8], which contains the unit structure.

［上記式（φ－１－２）中、
Ｒ^６は、それぞれ独立して、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のジアリールアミノ（２つのアリールは互いに連結基または単結合を介して結合していてもよい）、置換もしくは無置換のジヘテロアリールアミノ（２つのヘテロアリールは互いに連結基または単結合を介して結合していてもよい）、置換もしくは無置換のアリールヘテロアリールアミノ（アリールとヘテロアリールとは互いに連結基または単結合を介して結合していてもよい）、置換もしくは無置換のジアリールボリル（２つのアリールは単結合または連結基または単結合を介して結合していてもよい）、置換もしくは無置換のアルキル、置換もしくは無置換のアルコキシ、置換もしくは無置換のアリールオキシ、または置換もしくは無置換のアミノであり、
Ｒ^７は、それぞれ独立して、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のアルキル、または置換もしくは無置換のシクロアルキルである］
の単位構造を含む、上記［９］に記載の多環芳香族化合物。 [10] [φ]n is the following formula (φ-1-2):

[In the above formula (φ-1-2),
R ⁶ is each independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino (even if two aryls are bonded to each other via a linking group or a single bond) substituted or unsubstituted diheteroarylamino (two heteroaryls may be bonded to each other via a linking group or a single bond), substituted or unsubstituted arylheteroarylamino (aryl and heteroaryl may be bonded to each other via a linking group or a single bond), substituted or unsubstituted diarylboryl (two aryls may be bonded to each other via a single bond or a linking group or a single bond), substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstituted amino,
R ⁷ is each independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl]
The polycyclic aromatic compound according to the above [9], which contains the unit structure.

上記式（φ－２）中、
Ｘは、それぞれ独立して、＞Ｎ－Ｒ^１、＞Ｏ、＞Ｃ（－Ｒ^２）_２、＞Ｓｉ（－Ｒ^２）_２、＞Ｓ、または＞Ｓｅであり、
前記Ｒ^１は、水素、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のアルキル、または置換もしくは無置換のシクロアルキルであり、
前記Ｒ^２は、それぞれ独立して、水素、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のアルキル、または置換もしくは無置換のシクロアルキルであり、
この際、２つのＲ^２は互いに結合して環を形成していてもよく、
Ｒ^１またはＲ^２は、連結基または単結合により、ａ環、ｂ環、ｄ環、およびｅ環の少なくとも１つと結合して環を形成していてもよく、
Ｙは、それぞれ独立して、Ｂ、Ｐ、Ｐ＝Ｏ、Ｐ＝Ｓ、Ａｌ、Ｇａ、Ａｓ、Ｓｉ－Ｒ^３、またはＧｅ－Ｒ^３であり、
前記Ｒ^３は、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のアルキル、または置換もしくは無置換のシクロアルキルであり、
Ｚは、それぞれ独立して、－Ｃ（－Ｒ^４）＝または－Ｎ＝であり、この際、任意の「－Ｃ（－Ｒ^４）＝Ｃ（－Ｒ^４）－」は、「－Ｎ（－Ｒ^４）－」、「－Ｏ－」、「－Ｓ－」、「－Ｃ（－Ｒ^４）_２－」、「－Ｓｉ（－Ｒ^４）_２－」、または「－Ｓｅ－」に置き換わっていてもよく、前記「－Ｃ（－Ｒ^４）_２－」の２つのＲ^４同士および「－Ｓｉ（－Ｒ^４）_２－」の２つのＲ^４同士は、それぞれ独立して、単結合、－ＣＲ^５＝ＣＲ^５－、－Ｃ≡Ｃ－、－Ｎ（－Ｒ^５）－、－Ｏ－、－Ｓ－、－Ｃ（－Ｒ^５）_２－、－Ｓｉ（－Ｒ^５）_２－、－Ｃ（＝Ｏ）－または－Ｓｅ－を介して結合していてもよく、
前記Ｒ^４は、それぞれ独立して、水素、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のジアリールアミノ（２つのアリールは互いに連結基または単結合を介して結合していてもよい）、置換もしくは無置換のジヘテロアリールアミノ（２つのヘテロアリールは互いに連結基または単結合を介して結合していてもよい）、置換もしくは無置換のアリールヘテロアリールアミノ（アリールとヘテロアリールとは互いに連結基または単結合を介して結合していてもよい）、置換もしくは無置換のジアリールボリル（２つのアリールは単結合または連結基または単結合を介して結合していてもよい）、置換もしくは無置換のアルキル、置換もしくは無置換のアルコキシ、置換もしくは無置換のアリールオキシ、または置換もしくは無置換のアミノであり、
前記Ｒ^５は、それぞれ独立して、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のアルキル、または置換もしくは無置換のシクロアルキルである。 [11] The polycyclic aromatic compound according to [1] above, wherein [φ]n includes a unit structure of the following formula (φ-2):

In the above formula (φ-2),
X is each independently >NR ¹ , >O, >C(-R ² ) ₂ , >Si(-R ² ) ₂ , >S, or >Se;
The R ¹ is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl,
The R ² is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl,
In this case, two R ² may be bonded to each other to form a ring,
R ¹ or R ² may be bonded to at least one of ring a, ring b, ring d, and ring e through a linking group or a single bond to form a ring,
Y is each independently B, P, P=O, P=S, Al, Ga, As, Si-R ³ , or Ge-R ³ ,
The R ³ is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl,
Z is each independently -C(-R ⁴ )= or -N=, and in this case, any "-C(-R ⁴ )=C(-R ⁴ )-" is "-N (-R ⁴ )-", "-O-", "-S-", "-C(-R ⁴ ) _2- ", "-Si(-R ⁴ ) _2- ", or "-Se-" The two R ^4s in "-C(-R ⁴ ) ₂ --" and the two R ^4s in "-Si(-R ⁴ ) ₂ --" each independently represent Single bond, -CR ⁵ =CR ⁵ -, -C≡C-, -N(-R ⁵ )-, -O-, -S-, -C(-R ⁵ ) ₂ -, -Si(-R ⁵ ) ₂ -, may be bonded via -C(=O)- or -Se-,
The above R ⁴ is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino (two aryls are bonded to each other via a linking group or a single bond); ), substituted or unsubstituted diheteroarylamino (two heteroaryls may be bonded to each other via a linking group or a single bond), substituted or unsubstituted arylheteroarylamino (aryl and Heteroaryl may be bonded to each other via a linking group or a single bond), substituted or unsubstituted diarylboryl (two aryls may be bonded to each other via a single bond, a linking group, or a single bond) ), substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstituted amino,
Each R ⁵ is independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl.

の単位構造を含む、上記［１１］に記載の多環芳香族化合物。 [12] [φ]n is the following formula (φ-2-1):

The polycyclic aromatic compound according to the above [11], comprising the unit structure.

［上記式（φ－２－２）中、
Ｒ^６は、それぞれ独立して、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のジアリールアミノ（２つのアリールは互いに連結基または単結合を介して結合していてもよい）、置換もしくは無置換のジヘテロアリールアミノ（２つのヘテロアリールは互いに連結基または単結合を介して結合していてもよい）、置換もしくは無置換のアリールヘテロアリールアミノ（アリールとヘテロアリールとは互いに連結基または単結合を介して結合していてもよい）、置換もしくは無置換のジアリールボリル（２つのアリールは単結合または連結基または単結合を介して結合していてもよい）、置換もしくは無置換のアルキル、置換もしくは無置換のアルコキシ、置換もしくは無置換のアリールオキシ、または置換もしくは無置換のアミノであり、
Ｒ^７は、それぞれ独立して、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のアルキル、または置換もしくは無置換のシクロアルキルである］
の単位構造を含む、上記［１２］に記載の多環芳香族化合物。 [13] [φ]n is the following formula (φ-2-2):

[In the above formula (φ-2-2),
R ⁶ is each independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino (even if two aryls are bonded to each other via a linking group or a single bond) substituted or unsubstituted diheteroarylamino (two heteroaryls may be bonded to each other via a linking group or a single bond), substituted or unsubstituted arylheteroarylamino (aryl and heteroaryl may be bonded to each other via a linking group or a single bond), substituted or unsubstituted diarylboryl (two aryls may be bonded to each other via a single bond or a linking group or a single bond), substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstituted amino,
R ⁷ is each independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl]
The polycyclic aromatic compound according to the above [12], which contains the unit structure.

上記式（φ－３）中、
Ｘは、それぞれ独立して、＞Ｎ－Ｒ^１、＞Ｏ、＞Ｃ（－Ｒ^２）_２、＞Ｓｉ（－Ｒ^２）_２、＞Ｓ、または＞Ｓｅであり、
前記Ｒ^１は、水素、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のアルキル、または置換もしくは無置換のシクロアルキルであり、
前記Ｒ^２は、それぞれ独立して、水素、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のアルキル、または置換もしくは無置換のシクロアルキルであり、
この際、２つのＲ^２は互いに結合して環を形成していてもよく、
Ｒ^１またはＲ^２は、連結基または単結合により、ａ環、ｂ環、ｄ環、およびｅ環の少なくとも１つと結合して環を形成していてもよく、
Ｙは、それぞれ独立して、Ｂ、Ｐ、Ｐ＝Ｏ、Ｐ＝Ｓ、Ａｌ、Ｇａ、Ａｓ、Ｓｉ－Ｒ^３、またはＧｅ－Ｒ^３であり、
前記Ｒ^３は、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のアルキル、または置換もしくは無置換のシクロアルキルであり、
Ｚは、それぞれ独立して、－Ｃ（－Ｒ^４）＝または－Ｎ＝であり、この際、任意の「－Ｃ（－Ｒ^４）＝Ｃ（－Ｒ^４）－」は、「－Ｎ（－Ｒ^４）－」、「－Ｏ－」、「－Ｓ－」、「－Ｃ（－Ｒ^４）_２－」、「－Ｓｉ（－Ｒ^４）_２－」、または「－Ｓｅ－」に置き換わっていてもよく、前記「－Ｃ（－Ｒ^４）_２－」の２つのＲ^４同士および「－Ｓｉ（－Ｒ^４）_２－」の２つのＲ^４同士は、それぞれ独立して、単結合、－ＣＲ^５＝ＣＲ^５－、－Ｃ≡Ｃ－、－Ｎ（－Ｒ^５）－、－Ｏ－、－Ｓ－、－Ｃ（－Ｒ^５）_２－、－Ｓｉ（－Ｒ^５）_２－、－Ｃ（＝Ｏ）－または－Ｓｅ－を介して結合していてもよく、
前記Ｒ^４は、それぞれ独立して、水素、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のジアリールアミノ（２つのアリールは互いに連結基または単結合を介して結合していてもよい）、置換もしくは無置換のジヘテロアリールアミノ（２つのヘテロアリールは互いに連結基または単結合を介して結合していてもよい）、置換もしくは無置換のアリールヘテロアリールアミノ（アリールとヘテロアリールとは互いに連結基または単結合を介して結合していてもよい）、置換もしくは無置換のジアリールボリル（２つのアリールは単結合または連結基または単結合を介して結合していてもよい）、置換もしくは無置換のアルキル、置換もしくは無置換のアルコキシ、置換もしくは無置換のアリールオキシ、または置換もしくは無置換のアミノであり、
前記Ｒ^５は、それぞれ独立して、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のアルキル、または置換もしくは無置換のシクロアルキルである。 [14] The polycyclic aromatic compound according to [1] above, wherein [φ]n includes a unit structure of the following formula (φ-3):

In the above formula (φ-3),
X is each independently >NR ¹ , >O, >C(-R ² ) ₂ , >Si(-R ² ) ₂ , >S, or >Se;
The R ¹ is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl,
The R ² is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl,
In this case, two R ² may be bonded to each other to form a ring,
R ¹ or R ² may be bonded to at least one of ring a, ring b, ring d, and ring e through a linking group or a single bond to form a ring,
Y is each independently B, P, P=O, P=S, Al, Ga, As, Si-R ³ , or Ge-R ³ ,
The R ³ is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl,
Z is each independently -C(-R ⁴ )= or -N=, and in this case, any "-C(-R ⁴ )=C(-R ⁴ )-" is "-N (-R ⁴ )-", "-O-", "-S-", "-C(-R ⁴ ) _2- ", "-Si(-R ⁴ ) _2- ", or "-Se-" The two R ^4s in "-C(-R ⁴ ) ₂ --" and the two R ^4s in "-Si(-R ⁴ ) ₂ --" each independently represent Single bond, -CR ⁵ =CR ⁵ -, -C≡C-, -N(-R ⁵ )-, -O-, -S-, -C(-R ⁵ ) ₂ -, -Si(-R ⁵ ) ₂ -, may be bonded via -C(=O)- or -Se-,
The above R ⁴ is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino (two aryls are bonded to each other via a linking group or a single bond); ), substituted or unsubstituted diheteroarylamino (two heteroaryls may be bonded to each other via a linking group or a single bond), substituted or unsubstituted arylheteroarylamino (aryl and Heteroaryl may be bonded to each other via a linking group or a single bond), substituted or unsubstituted diarylboryl (two aryls may be bonded to each other via a single bond, a linking group, or a single bond) ), substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstituted amino,
Each R ⁵ is independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl.

の単位構造を含む、上記［１４］に記載の多環芳香族化合物。 [15] [φ]n is the following formula (φ-3-1):

The polycyclic aromatic compound according to the above [14], which contains the unit structure.

［上記式（φ－３－２）中、
Ｒ^６は、それぞれ独立して、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のジアリールアミノ（２つのアリールは互いに連結基または単結合を介して結合していてもよい）、置換もしくは無置換のジヘテロアリールアミノ（２つのヘテロアリールは互いに連結基または単結合を介して結合していてもよい）、置換もしくは無置換のアリールヘテロアリールアミノ（アリールとヘテロアリールとは互いに連結基または単結合を介して結合していてもよい）、置換もしくは無置換のジアリールボリル（２つのアリールは単結合または連結基または単結合を介して結合していてもよい）、置換もしくは無置換のアルキル、置換もしくは無置換のアルコキシ、置換もしくは無置換のアリールオキシ、または置換もしくは無置換のアミノであり、
Ｒ^７は、それぞれ独立して、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のアルキル、または置換もしくは無置換のシクロアルキルである］
の単位構造を含む、上記［１５］に記載の多環芳香族化合物。 [16] [φ]n is the following formula (φ-3-2):

[In the above formula (φ-3-2),
R ⁶ is each independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino (even if two aryls are bonded to each other via a linking group or a single bond) substituted or unsubstituted diheteroarylamino (two heteroaryls may be bonded to each other via a linking group or a single bond), substituted or unsubstituted arylheteroarylamino (aryl and heteroaryl may be bonded to each other via a linking group or a single bond), substituted or unsubstituted diarylboryl (two aryls may be bonded to each other via a single bond or a linking group or a single bond), substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstituted amino,
R ⁷ is each independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl]
The polycyclic aromatic compound according to the above [15], comprising the unit structure.

式中、Ｍｅはメチル、ｔＢｕはブチルである。 [17] The polycyclic aromatic compound according to [1] above, selected from the group consisting of the following formulas (1-1) to (1-7) and formula (2-11):

In the formula, Me is methyl and tBu is butyl.

[18] A reactive compound obtained by substituting the polycyclic aromatic compound described in any one of [1] to [17] above with a reactive substituent.

[19] A polymer compound obtained by polymerizing the reactive compound described in [18] above as a monomer, or a crosslinked polymer obtained by further crosslinking the polymer compound.

[20] A pendant polymer compound in which the main chain polymer is substituted with the reactive compound described in [18] above, or a pendant crosslinked polymer in which the pendant polymer compound is further crosslinked.

[21] An organic device material containing the polycyclic aromatic compound described in any one of [1] to [17] above.

[22] An organic device material containing the reactive compound described in [18] above.

[23] An organic device material containing the polymer compound or crosslinked polymer described in [19] above.

[24] An organic device material containing the pendant polymer compound or pendant polymer crosslinked product described in [20] above.

[25] Any of the above [21] to [24], wherein the organic device material is an organic electroluminescent element material, an organic field effect transistor material, an organic thin film solar cell material, or a wavelength conversion filter material. Materials for organic devices described in

[26] The material for an organic device according to the above [25], wherein the material for an organic electroluminescent element is a material for a light emitting layer.

[27] An ink composition comprising the polycyclic aromatic compound described in any one of [1] to [17] above and an organic solvent.

[28] An ink composition comprising the reactive compound described in [18] above and an organic solvent.

[29] An ink composition comprising a main chain polymer, the reactive compound described in [18] above, and an organic solvent.

[30] An ink composition comprising the polymer compound or crosslinked polymer described in [19] above and an organic solvent.

[31] An ink composition comprising the pendant polymer compound or pendant crosslinked polymer described in [20] above, and an organic solvent.

[32] A pair of electrodes consisting of an anode and a cathode, a polycyclic aromatic compound described in any of [1] to [17] above, which is disposed between the pair of electrodes, and a reaction described in [18] above. a polymer compound or crosslinked polymer described in [19] above, or an organic layer containing a pendant polymer compound or crosslinked polymer described in [20] above. Electroluminescent device.

[33] The organic electroluminescent device according to [32] above, wherein the organic layer is a light emitting layer.

[34] The light-emitting layer includes a host and the polycyclic aromatic compound, reactive compound, polymer compound, polymer crosslinked product, pendant type polymer compound, or pendant type polymer crosslinked product as a dopant. The organic electroluminescent device described in [33] above.

[35] The organic electroluminescent device according to [34] above, wherein the host is an anthracene-based compound, a fluorene-based compound, or a dibenzochrysene-based compound.

[36] At least one layer of an electron transport layer and an electron injection layer is arranged between the cathode and the light emitting layer, and at least one of the electron transport layer and the electron injection layer is made of a borane derivative, pyridine. Derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, quinolinol metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives and an azoline derivative, the organic electroluminescent device according to any one of [33] to [35] above.

[37] At least one of the electron transport layer and the electron injection layer further comprises an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal oxide, an alkali metal halide, and an alkaline earth metal oxide. , at least one selected from the group consisting of alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes. The organic electroluminescent device according to the above [36], comprising:

[38] At least one layer among the hole injection layer, hole transport layer, light emitting layer, electron transport layer, and electron injection layer is a polymer obtained by polymerizing a low molecular weight compound capable of forming each layer as a monomer. compound, or a polymer crosslinked product obtained by further crosslinking the polymer compound, or a pendant polymer compound obtained by reacting a low molecular compound capable of forming each layer with a main chain polymer, or the pendant polymer compound. The organic electroluminescent device according to any one of [32] to [37] above, comprising a pendant crosslinked polymer obtained by further crosslinking a molecular compound.

[39] A display device or a lighting device comprising the organic electroluminescent device according to any one of [32] to [38] above.

[40] A wavelength conversion filter comprising the wavelength conversion filter material described in [25] above.

According to a preferred embodiment of the present invention, it is possible to provide a polycyclic aromatic compound having a novel structure that can be used as a material for organic devices such as a material for organic EL elements, and the polycyclic aromatic compound By using this, it is possible to provide an excellent organic device such as an organic EL element.

Specifically, the present inventors have discovered that polycyclic aromatic compounds in which aromatic rings are connected with hetero elements such as boron, phosphorus, oxygen, nitrogen, and sulfur have a large HOMO-LUMO gap depending on the method of connecting the hetero elements. It has also been found that the film has a small HOMO-LUMO gap (band gap Eg in a thin film). This is because the 6-membered ring containing a hetero element has low aromaticity, which may suppress or promote the reduction of the HOMO-LUMO gap due to the expansion of the conjugated system and the localization or delocalization of each orbital. This is thought to be the cause. These polycyclic aromatic compounds have a robust skeleton in which 5- or 6-membered rings are condensed or connected, so the half-width of the fluorescence peak is narrow, making them useful as emitters for organic EL devices. In this case, luminescence with high color purity can be obtained. In addition, by selecting the method of linking the heteroelements, it exhibits thermally activated delayed fluorescence, making it possible to obtain high efficiency when used as an emitter of an organic EL device. Furthermore, by introducing a substituent, the energies of HOMO and LUMO can be changed arbitrarily, so it is possible to optimize the ionization potential and electron affinity depending on the surrounding materials. However, the present invention is not particularly limited to these principles.

FIG. 1 is a schematic cross-sectional view showing an organic EL element according to the present embodiment.

1. Polycyclic aromatic compounds
<Description of the overall structure of the compound>
The present invention is a compound represented by the following general formula (1) or general formula (2) (hereinafter also referred to as a "polycyclic aromatic compound").

In the above general formulas (1) and (2), [φ]n is at least one type of unit structure selected from the group consisting of the following formulas (φ-a-1) to (φ-a-6). and the unit structure of the following formula (φ-b) are connected in total to n units. At this time, the formulas (φ-a-1) to (φ-a-6) and the formula (φ-b) are alternately connected. Further, n is an integer of 3 or more, preferably 3 to 11, more preferably 3 to 9, still more preferably 3, 5, or 7, and particularly preferably 3 or 5.

Further, each X is independently >NR ¹ , >O, >C(-R ² ) ₂ , >Si(-R ² ) ₂ , >S, or >Se.
Y is each independently B, P, P=O, P=S, Al, Ga, As, Si-R ³ , or Ge-R ³ .
Z is each independently -C(-R ⁴ )= or -N= (any "-C(-R ⁴ )=C(-R ⁴ )-" is "-N(-R ⁴ )-”, “-O-”, “-S-”, “-C(-R ⁴ ) _2- ”, “-Si(-R ⁴ ) _2- ”, or “-Se-”. In this case, the two R ^4s in "-C(-R ⁴ ) ₂ -" and the two R ^4s in "-Si(-R ⁴ ) ₂ -" each independently form a single Bond, -CR ⁵ =CR ⁵ -, -C≡C-, -N(-R ⁵ )-, -O-, -S-, -C(-R ⁵ ) ₂ -, -Si(-R ⁵ ) _2- , -C(=O)- or -Se-).
Further, two different Zs in the c ring, Z in the c ring and Z in the d ring, Z in the c ring and Z in the e ring may be bonded to each other via a linking group or a single bond to form a ring.
Here, at least one of the a ring, b ring, c ring, d ring, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl in the general formula (1) or general formula (2), It may be condensed with at least one cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one "-CH ₂ -" in the cycloalkane is replaced with "-O-" may have been done.
Furthermore, in the general formula (1) or general formula (2), at least one hydrogen may be replaced with cyano, halogen, or deuterium.

Note that R ¹ is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl.
Each R ² is independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl.
In this case, two R ² may be bonded to each other to form a ring, and R ¹ or R ² may be connected to at least one of ring a, ring b, ring d, and ring e through a linking group or a single bond. They may be combined with each other to form a ring.
The above R ³ is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl.
The above R ⁴ is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino (two aryls are bonded to each other via a linking group or a single bond); ), substituted or unsubstituted diheteroarylamino (two heteroaryls may be bonded to each other via a linking group or a single bond), substituted or unsubstituted arylheteroarylamino (aryl and Heteroaryl may be bonded to each other via a linking group or a single bond), substituted or unsubstituted diarylboryl (two aryls may be bonded to each other via a single bond, a linking group, or a single bond) ), substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstituted amino.
Each R ⁵ is independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl.

<Explanation of the terminal structure constituting the compound>
The two d-rings which are the terminal structures of the polycyclic aromatic compound can have various structures. In this case, the two d rings in general formula (1) may have a symmetrical structure or may have an asymmetrical structure. In one embodiment, general formula (1) is selected from the group consisting of formulas (1-A) to (1-L) below.

In the above formulas (1-A) to (1-L), R is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl. It is. Among these, R is preferably hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted alkyl, and is hydrogen, phenyl, methyl, ethyl, propyl, butyl, t-butyl, propyl, hexyl, 2-ethylhexyl. , heptyl, octyl, nonyl, decyl, adamantyl (Ad), more preferably hydrogen, phenyl, methyl, t-butyl, hexyl, 2-ethylhexyl, heptyl, decyl, hydrogen, methyl, Particularly preferred is t-butyl.

Formulas (1-A) to (1-L) include, for example, formulas (1-A-1) to (1-A-11), and formulas (1-B-1) to (1-B-3). , formulas (1-C-1) to (1-C-3), formulas (1-D-1) to (1-D-3), formulas (1-E-1) to (1-E-3) ), formula (1-F-1) to (1-F-4), formula (1-G-1) to (1-G-4), formula (1-H-1), formula (1-I -1), formula (1-J-1), formula (1-K-1), and formulas (1-L-1) to (1-L-2).

Among these, formula (1) is preferably formula (1-A), formula (1-B), formula (1-D), or formula (1-J), and formula (1-A), The formula (1-J) is more preferable, and the formula (1-A-1), the formula (1-A-2), the formula (1-A-5), and the formula (1-J-1). More preferably, formula (1-A-2), formula (1-A-5), and formula (1-J-1) are particularly preferred.

<Explanation of unit structure constituting the compound>
[φ]n, which is a unit structure of a polycyclic aromatic compound, has at least one unit structure selected from the group consisting of the above formulas (φ-a-1) to (φ-a-6), and the above formula It has a structure in which a total of n unit structures of (φ-b) are connected. At this time, formulas (φ-a-1) to (φ-a-6) and formula (φ-b) are alternately connected.

When the polycyclic aromatic compound is represented by the general formula (1), both ends of the unit structure (that is, the unit structure connected to the d ring of the general formula (1)) are represented by the formulas (φ-a-1) to (φ-a-6) is preferable, and any of the formulas (φ-a-1) to (φ-a-5) is preferable.
Furthermore, when the polycyclic aromatic compound is represented by general formula (2), [φ]n preferably includes at least one of formulas (φ-a-2) to (φ-a-6). , more preferably includes at least one of formula (φ-a-2) and formula (φ-a-5), and at least one of formula (φ-a-3) and (φ-a-4). , formula (φ-a-2) and formula (φ-a-3), or formula (φ-a-4) and formula (φ-a-5). Furthermore, when the polycyclic aromatic compound is represented by general formula (2), [φ]n preferably includes formula (φ-a-1).

[Formula (φ-a-1)]
Formula (φ-a-1) is expressed by the following formula.

In the above formula (φ-a-1), X is each independently >N-R ¹ , >O, >C(-R ² ) ₂ , >Si(-R ² ) ₂ , >S, or >Se. From the viewpoint of stability, X is preferably >NR ¹ , >O, >S, or >C(-R ² ) ₂ , and more preferably >NR ¹ or >O. Furthermore, from the viewpoint of short wavelength light emission, >NR ¹ , >O, or >C(-R ² ) ₂ is preferable, and >O or >C(-R ² ) ₂ is more preferable.

R ¹ is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl.

Each R ² is independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl.

Here, two R ² may be bonded to each other to form a ring.
Furthermore, R ¹ or R ² may be bonded to at least one of ring a, ring b, ring d, and ring e through a linking group or a single bond to form a ring.

であることが好ましく、＞Ｏ、＞Ｓ、または以下の式（Ｘ－１－１）～（Ｘ－１－２０）、式（Ｘ－３－１）、式（Ｘ－５－１）：

であることがより好ましく、＞Ｏ、＞Ｓ、式（Ｘ－１－１）、式（Ｘ－１－２）、式（Ｘ－１－６）、式（Ｘ－１－１３）であることがさらに好ましく、式（Ｘ－１－６）、式（Ｘ－１－１３）であることが特に好ましい。 In one embodiment, X is each independently >O, >S, or the following formulas (X-1) to (X-7):

Preferably, >O, >S, or the following formulas (X-1-1) to (X-1-20), formula (X-3-1), formula (X-5-1):

More preferably, >O, >S, formula (X-1-1), formula (X-1-2), formula (X-1-6), formula (X-1-13) is more preferable, and formula (X-1-6) and formula (X-1-13) are particularly preferable.

In addition, in the above formulas (X-1) to (X-7), R is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted alkyl. It is cycloalkyl. Among these, R is preferably hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted alkyl, more preferably hydrogen, phenyl, methylphenyl, t-butylphenyl, biphenyl, hydrogen, phenyl , methylphenyl, and t-butylphenyl are more preferred.

In the above formula (φ-a-1), Y is each independently B, P, P=O, P=S, Al, Ga, As, Si-R ³ , or Ge-R ³ . Yes, B is preferred.

The above R ³ is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl.

Z is each independently -C(-R ⁴ )= or -N=, and in this case, any "-C(-R ⁴ )=C(-R ⁴ )-" is "-N (-R ⁴ )-", "-O-", "-S-", "-C(-R ⁴ ) _2- ", "-Si(-R ⁴ ) _2- ", or "-Se-" The two R ^4s in "-C(-R ⁴ ) ₂ --" and the two R ^4s in "-Si(-R ⁴ ) ₂ --" each independently represent Single bond, -CR ⁵ =CR ⁵ -, -C≡C-, -N(-R ⁵ )-, -O-, -S-, -C(-R ⁵ ) ₂ -, -Si(-R ⁵ ) ₂ -, -C(=O)- or -Se- may be bonded to each other. Furthermore, when any "-C(-R ⁴ )=C(-R ⁴ )-" is replaced with "-N(-R ⁴ )-", "-O-", "-S-", etc. The c-ring becomes a 5-membered ring.

The above R ⁴ is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino (two aryls are bonded to each other via a linking group or a single bond); ), substituted or unsubstituted diheteroarylamino (two heteroaryls may be bonded to each other via a linking group or a single bond), substituted or unsubstituted arylheteroarylamino (aryl and Heteroaryl may be bonded to each other via a linking group or a single bond), substituted or unsubstituted diarylboryl (two aryls may be bonded to each other via a single bond, a linking group, or a single bond) ), substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstituted amino.

Each R ⁵ is independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl.

Two Zs in different c rings, Z in the c ring and Z in the d ring, Z in the c ring and Z in the e ring may be bonded to each other via a linking group or a single bond to form a ring. For example, when Z of one of the two c-rings in formula (φ-a-1) and Z of the other c-ring are bonded together through a single bond to form a ring, the following formula ( It has a structure of φ-a-1'). Z in the c ring may form a ring with Z in the d ring, Z in the e ring, etc. that may be adjacent to each other by a single bond or a connecting group, preferably a single bond.

であることが好ましく、式（φ－ａ－１－Ａ）、式（φ－ａ－１－Ｂ）であることがより好ましく、以下の式（φ－ａ－１－Ａ’）、式（φ－ａ－１－Ｂ’）：

であることがさらに好ましく、式（φ－ａ－１－Ｂ’）であることが特に好ましい。 In a preferred embodiment, formula (φ-a-1) is each independently one of the following formulas (φ-a-1-A) to (φ-a-1-AL):

It is preferable that the formula (φ-a-1-A), the formula (φ-a-1-B) is more preferable, and the following formula (φ-a-1-A'), the formula ( φ-a-1-B'):

More preferably, the formula (φ-a-1-B') is particularly preferred.

In addition, in the above formula (φ-a-1-A) to formula (φ-a-1-AL), formula (φ-a-1-A'), and formula (φ-a-1-B') , X are as described above.

Further, R is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl. Among these, in formula (φ-a-1-A') and formula (φ-a-1-B'), R may be hydrogen, substituted or unsubstituted aryl, or substituted or unsubstituted alkyl. Preferred are hydrogen, phenyl, methylphenyl, t-butylphenyl, and biphenyl, and even more preferred are hydrogen, phenyl, methylphenyl, and t-butylphenyl.

であることが好ましく、式（φ－ａ－１－Ｂ’１）であることがより好ましい。 In one embodiment, the formula (φ-a-1) is the following formula (φ-a-1-A'1), the formula (φ-a-1-B'1):

is preferably, and more preferably is the formula (φ-a-1-B'1).

Note that R is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl. Among these, in formula (φ-a-1-A'1) and formula (φ-a-1-B'1), R is hydrogen, substituted or unsubstituted aryl, or substituted or unsubstituted alkyl. It is preferably hydrogen, phenyl, methylphenyl, t-butylphenyl, or biphenyl, and even more preferably hydrogen, phenyl, methylphenyl, or t-butylphenyl.

であることが好ましく、式（φ－ａ－１－１）～（φ－ａ－１－４６）であることがより好ましく、式（φ－ａ－１－２４）～（φ－ａ－１－４６）であることがさらに好ましく、式（φ－ａ－１－２５）、（φ－ａ－１－２６）、（φ－ａ－１－２９）、（φ－ａ－１－３２）～（φ－ａ－１－３５）、（φ－ａ－１－３９）～（φ－ａ－１－４２）、（φ－ａ－１－４５）、（φ－ａ－１－４６）であることがより好ましく、式（φ－ａ－１－３４）、式（φ－ａ－１－４０）、式（φ－ａ－１－４１）、式（φ－ａ－１－４６）であることが特に好ましい。 In one embodiment, formulas (φ-a-1) are each independently represented by formulas (φ-a-1-1) to (φ-a-1-90):

is preferable, formulas (φ-a-1-1) to (φ-a-1-46) are more preferable, and formulas (φ-a-1-24) to (φ-a-1 -46), and the formulas (φ-a-1-25), (φ-a-1-26), (φ-a-1-29), (φ-a-1-32) ~(φ-a-1-35), (φ-a-1-39) ~(φ-a-1-42), (φ-a-1-45), (φ-a-1-46) More preferably, formula (φ-a-1-34), formula (φ-a-1-40), formula (φ-a-1-41), formula (φ-a-1-46) It is particularly preferable that

[Formula (φ-a-2) and Formula (φ-a-3)]
Formula (φ-a-2) and formula (φ-a-3) are each represented by the following formula.

In the above formulas (φ-a-2) and (φ-a-3), X, Y, and Z are the same as those described in the above formula (φ-a-1).

であることが好ましい。 In a preferred embodiment, formula (φ-a-2) and formula (φ-a-3) each independently represent the following formula (φ-a-2-A) and formula (φ-a-3 -A):

It is preferable that

Note that R is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl. Among these, in formula (φ-a-2-A) and formula (φ-a-3-A), R is preferably hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted alkyl, Hydrogen, phenyl, methylphenyl, t-butylphenyl, and biphenyl are more preferred, and hydrogen, phenyl, methylphenyl, and t-butylphenyl are even more preferred.

Furthermore, in formula (φ-a-2-A) and formula (φ-a-3-A), Rx is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted It may be alkyl, substituted or unsubstituted cycloalkyl, or it may form a ring with adjacent d-ring or e-ring through a single bond or a linking group. For example, when formula (φ-a-2-A) is linked to ring e having a phenyl structure, Rx can form a 5-membered ring with ring e through a single bond, as shown in the formula below. .

であることが好ましく、式（φ－ａ－２－３）、式（φ－ａ－３－３）であることがより好ましい。なお、式（φ－ａ－２－４）～（φ－ａ－２－６）および式（φ－ａ－３－４）～式（φ－ａ－３－６）において、「＊」は隣接するｄ環またはｅ環と結合する単結合を意味する。 In one embodiment, formula (φ-a-2) and formula (φ-a-3) are each independently the following formulas (φ-a-2-1) to (φ-a-2-6 ) and formulas (φ-a-3-1) to (φ-a-2-6):

is preferable, and formula (φ-a-2-3) and formula (φ-a-3-3) are more preferable. In addition, in formulas (φ-a-2-4) to (φ-a-2-6) and formulas (φ-a-3-4) to (φ-a-3-6), "*" It means a single bond bonding to the adjacent d-ring or e-ring.

[Formula (φ-a-4) and Formula (φ-a-5)]
Formula (φ-a-4) and formula (φ-a-5) are represented by the following formulas.

In the above formulas (φ-a-4) and (φ-a-5), X, Y, and Z are the same as those described in the above formula (φ-a-1).

であることが好ましい。 In a preferred embodiment, formula (φ-a-4) and formula (φ-a-5) each independently represent the following formula (φ-a-4-A) and formula (φ-a-5 -A):

It is preferable that

Note that R is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl. Among these, in formula (φ-a-4-A) and formula (φ-a-5-A), R is preferably hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted alkyl, Hydrogen, phenyl, methylphenyl, t-butylphenyl, and biphenyl are more preferred, and hydrogen, phenyl, methylphenyl, and t-butylphenyl are even more preferred.

Furthermore, Rx is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, or is adjacent to each other by a single bond or a linking group. It may form a ring with d-ring or e-ring.

であることが好ましく、式（φ－ａ－４－３）、式（φ－ａ－５－３）であることがより好ましい。なお、式（φ－ａ－４－４）～（φ－ａ－４－６）および式（φ－ａ－５－４）～式（φ－ａ－５－６）において、「＊」は隣接するｄ環またはｅ環と結合する単結合を意味する。 In one embodiment, formula (φ-a-4) and formula (φ-a-5) are each independently the following formulas (φ-a-4-1) to (φ-a-4-6 ) and formulas (φ-a-5-1) to (φ-a-5-6):

is preferable, and formula (φ-a-4-3) and formula (φ-a-5-3) are more preferable. In addition, in formulas (φ-a-4-4) to (φ-a-4-6) and formulas (φ-a-5-4) to (φ-a-5-6), "*" It means a single bond bonding to the adjacent d-ring or e-ring.

[Formula (φ-a-6)]
Formula (φ-a-6) is expressed by the following formula.

In the above formula (φ-a-6), X, Y, and Z are the same as those described in the above formula (φ-a-1).

であることが好ましい。 In a preferred embodiment, the formula (φ-a-6) is each independently the following formula (φ-a-6-A):

It is preferable that

Note that R is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl. Among these, in formula (φ-a-6), R is preferably hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted alkyl, and hydrogen, phenyl, methylphenyl, t-butylphenyl, biphenyl More preferably, hydrogen, phenyl, methylphenyl, and t-butylphenyl are more preferable.

Furthermore, Rx is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl, or is adjacent to each other by a single bond or a linking group. It may form a ring with d-ring or e-ring.

であることが好ましく、式（φ－ａ－６－４）であることがより好ましい。なお、式（φ－ａ－６－５）～（φ－ａ－６－１０）において、「＊」は隣接するｄ環またはｅ環と結合する単結合を意味する。 In one embodiment, formulas (φ-a-6) are each independently the following formulas (φ-a-6-1) to (φ-a-6-10):

It is preferably the formula (φ-a-6-4), and more preferably the formula (φ-a-6-4). In addition, in formulas (φ-a-6-5) to (φ-a-6-10), “*” means a single bond bonded to the adjacent d ring or e ring.

上記式（φ－ｂ）において、Ｚは、上記式（φ－ａ－１）に記載のものと同様である。 [Formula (φ-b)]
The formula (φ-b) is expressed by the following formula.

In the above formula (φ-b), Z is the same as that described in the above formula (φ-a-1).

であることが好ましく、式（φ－ｂ－１）であることがより好ましい。 In a preferred embodiment, the formulas (φ-b) are each independently the following formulas (φ-b-1) to (φ-b-6):

is preferable, and formula (φ-b-1) is more preferable.

In one embodiment, it is preferred that X is >NR ¹ , Y is B, and Z is -C(-R ⁴ )=. This results in a robust skeleton, resulting in high stability, a favorable HOMO-LUMO gap, which increases luminous efficiency, and facilitates reverse conversion from triplet state to singlet state, resulting in thermally activated delayed fluorescence ( TADF) has the effect of increasing luminous efficiency and making it easier to emit light with a long wavelength (for example, green light).

Further, in one embodiment, [φ]n preferably includes a unit structure of formula (φ-a-1) and a unit structure of formula (φ-b), and [φ]n includes a unit structure of formula (φ-a-1). It is more preferable to consist of a unit structure of the structure and formula (φ-b). As a result, two adjacent [φ]s form a para-position bond, so that [φ]n has a linear shape, and can have excellent luminous efficiency, high luminous intensity, high stability, and the like.

Further, in one embodiment, [φ]n preferably includes the unit structures of formulas (φ-a-1) to (φ-a-3) and the unit structure of formula (φ-b), It is preferable to consist of a unit structure of formulas (φ-a-1) to (φ-a-3) and a unit structure of formula (φ-b). As a result, two adjacent [φ] have at least one meta-position bond, so that [φ]n has a curved shape, resulting in excellent luminous efficiency, high luminous intensity, etc., and control of rigidity and stability. can do.

In one embodiment, n is an integer of 3 or more, preferably 3 to 11, more preferably 3 to 9, still more preferably 3, 5, 7, particularly preferably 3, 5. . When n is 3 or more, the emission wavelength can be made long, and for example, green light, which is one of the three primary colors of light, can be emitted. Furthermore, in a preferred embodiment, by setting n to 11 or less, it is possible to achieve a suitable balance between light emission characteristics and physical properties (stability, rigidity, etc.).

In one embodiment, each R ⁴ is independently hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted diphenylamino. In another embodiment, at least one of R ⁴ is alkyl having 8 to 30 carbon atoms. By controlling ^R4 , luminous efficiency, thermally activated delayed fluorescence (TADF), fluorescence wavelength, and physical properties can be controlled.

<Explanation of connection form of unit structure>
n of [φ]n in general formulas (1) and (2) is 3 or more as described above, and the connection form thereof is not particularly limited.

の単位構造の少なくとも１つを含むことが好ましい。
上記式（φ－１）～（φ－３）において、Ｘは、それぞれ独立して、＞Ｎ－Ｒ^１、＞Ｏ、＞Ｃ（－Ｒ^２）_２、＞Ｓｉ（－Ｒ^２）_２、＞Ｓ、または＞Ｓｅである。
前記Ｒ^１は、水素、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のアルキル、または置換もしくは無置換のシクロアルキルである。
前記Ｒ^２は、それぞれ独立して、水素、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のアルキル、または置換もしくは無置換のシクロアルキルである。
この際、２つのＲ^２は互いに結合して環を形成していてもよい。
Ｒ^１またはＲ^２は、連結基または単結合により、ａ環、ｂ環、ｄ環、およびｅ環の少なくとも１つと結合して環を形成していてもよい。
Ｙは、それぞれ独立して、Ｂ、Ｐ、Ｐ＝Ｏ、Ｐ＝Ｓ、Ａｌ、Ｇａ、Ａｓ、Ｓｉ－Ｒ^３、またはＧｅ－Ｒ^３である。
前記Ｒ^３は、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のアルキル、または置換もしくは無置換のシクロアルキルである。
Ｚは、それぞれ独立して、－Ｃ（－Ｒ^４）＝または－Ｎ＝であり、この際、任意の「－Ｃ（－Ｒ^４）＝Ｃ（－Ｒ^４）－」は、「－Ｎ（－Ｒ^４）－」、「－Ｏ－」、「－Ｓ－」、「－Ｃ（－Ｒ^４）_２－」、「－Ｓｉ（－Ｒ^４）_２－」、または「－Ｓｅ－」に置き換わっていてもよく、前記「－Ｃ（－Ｒ^４）_２－」の２つのＲ^４同士および「－Ｓｉ（－Ｒ^４）_２－」の２つのＲ^４同士は、それぞれ独立して、単結合、－ＣＲ^５＝ＣＲ^５－、－Ｃ≡Ｃ－、－Ｎ（－Ｒ^５）－、－Ｏ－、－Ｓ－、－Ｃ（－Ｒ^５）_２－、－Ｓｉ（－Ｒ^５）_２－、－Ｃ（＝Ｏ）－または－Ｓｅ－を介して結合していてもよい。
前記Ｒ^４は、それぞれ独立して、水素、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のジアリールアミノ（２つのアリールは互いに連結基または単結合を介して結合していてもよい）、置換もしくは無置換のジヘテロアリールアミノ（２つのヘテロアリールは互いに連結基または単結合を介して結合していてもよい）、置換もしくは無置換のアリールヘテロアリールアミノ（アリールとヘテロアリールとは互いに連結基または単結合を介して結合していてもよい）、置換もしくは無置換のジアリールボリル（２つのアリールは単結合または連結基または単結合を介して結合していてもよい）、置換もしくは無置換のアルキル、置換もしくは無置換のアルコキシ、置換もしくは無置換のアリールオキシ、または置換もしくは無置換のアミノである。
前記Ｒ^５は、それぞれ独立して、置換もしくは無置換のアリール、置換もしくは無置換のヘテロアリール、置換もしくは無置換のアルキル、または置換もしくは無置換のシクロアルキルである。 In one embodiment, [φ]n is expressed by the following formulas (φ-1) to (φ-3):

It is preferable that at least one of the following unit structures is included.
In the above formulas (φ-1) to (φ-3), X is independently >NR ¹ , >O, >C(-R ² ) ₂ , >Si(-R ² ) ₂ , >S or >Se.
The R ¹ is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl.
Each R ² is independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl.
In this case, two R ² may be bonded to each other to form a ring.
R ¹ or R ² may be bonded to at least one of ring a, ring b, ring d, and ring e through a linking group or a single bond to form a ring.
Y is each independently B, P, P=O, P=S, Al, Ga, As, Si-R ³ , or Ge-R ³ .
The above R ³ is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl.
Z is each independently -C(-R ⁴ )= or -N=, and in this case, any "-C(-R ⁴ )=C(-R ⁴ )-" is "-N (-R ⁴ )-", "-O-", "-S-", "-C(-R ⁴ ) _2- ", "-Si(-R ⁴ ) _2- ", or "-Se-" The two R ^4s in "-C(-R ⁴ ) ₂ --" and the two R ^4s in "-Si(-R ⁴ ) ₂ --" each independently represent Single bond, -CR ⁵ =CR ⁵ -, -C≡C-, -N(-R ⁵ )-, -O-, -S-, -C(-R ⁵ ) ₂ -, -Si(-R ⁵ ) ₂ -, -C(=O)- or -Se- may be bonded to each other.
The above R ⁴ is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino (two aryls are bonded to each other via a linking group or a single bond); ), substituted or unsubstituted diheteroarylamino (two heteroaryls may be bonded to each other via a linking group or a single bond), substituted or unsubstituted arylheteroarylamino (aryl and Heteroaryl may be bonded to each other via a linking group or a single bond), substituted or unsubstituted diarylboryl (two aryls may be bonded to each other via a single bond, a linking group, or a single bond) ), substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstituted amino.
Each R ⁵ is independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl.

Formula (φ-1) has a structure in which two formulas (φ-a-1) are connected via formula (φ-b) so that the formulas (φ-a-1) are anti-type to each other. have Such an anti-type arrangement tends to weaken the multiple resonance effect and provide light emission with a large ΔEST and a narrow half-width. In addition, having a robust skeleton tends to provide high stability and light emission with a narrow half-width. In this case, when X is >N-R ¹ , >O, >S, or >C(-R ² ) ₂ , preferably >N-R ¹ or >O, high stability tends to be obtained. Also, when X is >NR ¹ , >O, or >C(-R ² ) ₂ , short wavelength light emission tends to be obtained. When Y is P, P=O, and P=S, there is a tendency to obtain shorter wavelength light emission and a large ΔEST, and when it is B, there is a tendency to obtain longer wavelength light emission and a small ΔEST.

Formula (φ-2) has a structure in which two formulas (φ-a-1) are connected to each other in a thin manner via formula (φ-b). have Such a thin arrangement tends to strengthen the multiple resonance effect and provide high TADF properties and light emission with a narrow half-width. In this case, when X is >N-R ¹ , >O, >S, or >C(-R ² ) ₂ , preferably >N-R ¹ or >O, high stability tends to be obtained. When X is >NR ¹ , >O, or >C(-R ² ) ₂ , short wavelength light emission tends to be obtained. When Y is P, P=O, or P=S, there is a tendency to obtain shorter wavelength emission and a large ΔEST, and when Y is B, longer wavelength emission and small ΔEST tend to be obtained.

Formula (φ-3) is a structure in which formula (φ-a-1), formula (φ-a-2), and formula (φ-a-3) are connected via formula (φ-b). has. Such an arrangement tends to strengthen the multiple resonance effect and provide high TADF properties and light emission with a narrow half-width. In this case, when X is >N-R ¹ , >O, >S, or >C(-R ² ) ₂ , preferably >N-R ¹ or >O, high stability tends to be obtained. When X is >NR ¹ , >O, or >C(-R ² ) ₂ , short wavelength light emission tends to be obtained. When Y is P, P=O, or P=S, shorter wavelength light emission and a larger ΔEST tend to be obtained, and when Y is B, longer wavelength light emission and smaller ΔEST tend to be obtained.

の単位構造の少なくとも１つを含むことが好ましい。 In one embodiment, [φ]n is expressed by the following formulas (φ-1-1) to (φ-3-1):

It is preferable that at least one of the following unit structures is included.

Formula (φ-1-1) is, in the above formula (φ-1), X is NR ¹ , Y is B, Z is CR ⁴ , and two different c rings This is a structure in which z is bonded through a single bond to form a ring. This may result in high stability, suitable fluorescence wavelength and ΔEST.

Formula (φ-2-1), in the above formula (φ-2), X is N-R ¹ , Y is B, Z is C-R ⁴ , and two different c rings This is a structure in which z is bonded through a single bond to form a ring. This may result in high stability, suitable fluorescence wavelength and ΔEST.

Formula (φ-3-1), in the above formula (φ-3), X is NR ¹ , Y is B, Z is CR ⁴ , and two different c rings This is a structure in which z is bonded through a single bond to form a ring. This may result in high stability, suitable fluorescence wavelength and ΔEST.

の単位構造の少なくとも１つを含むことが好ましい。 In one embodiment, [φ]n is expressed by the following formulas (φ-1-2) to (φ-3-2):

It is preferable that at least one of the following unit structures is included.

In this case, R ⁴ is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino (two aryls are connected to each other via a linking group or a single bond). ), substituted or unsubstituted diheteroarylamino (two heteroaryls may be bonded to each other via a linking group or a single bond), substituted or unsubstituted arylheteroarylamino ( Aryl and heteroaryl may be bonded to each other via a linking group or a single bond), substituted or unsubstituted diarylboryl (two aryls may be bonded to each other via a single bond, a linking group, or a single bond), ), substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstituted amino. Among these, in formulas (φ-1-2) to (φ-3-2), R ⁴ is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted alkyl. hydrogen, substituted or unsubstituted alkyl is more preferable, hydrogen, methyl, ethyl, propyl, butyl, i-butyl, s-butyl, t-butyl, pentyl, hexyl, 2-ethylhexyl, heptyl. , octyl, nonyl, decyl are more preferred, hydrogen, methyl, t-butyl, 2-ethylhexyl are particularly preferred, methyl, t-butyl are very preferred, and methyl is most preferred. preferable.

R ⁶ is each independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino (even if two aryls are bonded to each other via a linking group or a single bond) substituted or unsubstituted diheteroarylamino (two heteroaryls may be bonded to each other via a linking group or a single bond), substituted or unsubstituted arylheteroarylamino (aryl and heteroaryl may be bonded to each other via a linking group or a single bond), substituted or unsubstituted diarylboryl (two aryls may be bonded to each other via a single bond or a linking group or a single bond), substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstituted amino. Among these, in formulas (φ-1-2) to (φ-3-2), R ⁶ may be substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or substituted or unsubstituted alkyl. Preferably, substituted or unsubstituted alkyl is preferred, and examples include methyl, ethyl, propyl, butyl, i-butyl, s-butyl, t-butyl, pentyl, hexyl, 2-ethylhexyl, heptyl, octyl, nonyl, and decyl. More preferably, methyl, t-butyl, and 2-ethylhexyl are particularly preferred, methyl and t-butyl are very preferred, and methyl is most preferred.

Further, R ⁷ is each independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl. Among these, in formulas (φ-1-2) to (φ-3-2), R ⁶ is preferably substituted or unsubstituted aryl, substituted or unsubstituted alkyl, substituted or unsubstituted phenyl , methyl, ethyl, propyl, butyl, i-butyl, s-butyl, t-butyl, pentyl, hexyl, 2-ethylhexyl, heptyl, octyl, nonyl, decyl, and more preferably trimethylphenyl, methyl, t- Butyl and 2-ethylhexyl are more preferred, and trimethylphenyl, methyl and t-butyl are particularly preferred.

That is, formulas (φ-1-2) to (φ-3-2) are structures having substituents at predetermined positions in the above formulas (φ-1-1) to (φ-3-1). . This may result in high stability, suitable fluorescence wavelength and ΔEST.

In one embodiment, when n is 3, [φ]n preferably has the structure of the above formulas (φ-1-2) to (φ-2-2).

In one embodiment, when n is 5, [φ]n preferably has the structure of the following formulas (φ-4) to (φ-5).

In one embodiment, when n is 7, [φ]n preferably has the structure of the following formulas (φ-6) to (φ-10).

<Specific explanation of rings and substituents>
Next, details of the rings and substituents enumerated in the above description will be explained together.

The "aryl ring" is, for example, an aryl ring having 6 to 30 carbon atoms, preferably an aryl ring having 6 to 20 carbon atoms, an aryl ring having 6 to 16 carbon atoms, an aryl ring having 6 to 12 carbon atoms, or an aryl ring having 6 to 12 carbon atoms. These include 6 to 10 aryl rings.
Specific "aryl rings" include, for example, a monocyclic benzene ring, a fused bicyclic naphthalene ring, a fused tricyclic acenaphthylene ring, fluorene ring, phenalene ring, phenanthrene ring, or anthracene ring. , a fused tetracyclic ring such as a triphenylene ring, a pyrene ring, or a naphthacene ring, or a fused pentacyclic ring such as a perylene ring or a pentacene ring.

"Heteroaryl ring" is, for example, a heteroaryl ring having 2 to 30 carbon atoms, preferably a heteroaryl ring having 2 to 25 carbon atoms, a heteroaryl ring having 2 to 20 carbon atoms, or a heteroaryl ring having 2 to 15 carbon atoms. These include an aryl ring, a heteroaryl ring having 2 to 10 carbon atoms, and the like. Further, the "heteroaryl ring" is, for example, a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.
Specific "heteroaryl rings" include, for example, pyrrole ring, oxazole ring, isoxazole ring, thiazole ring, isothiazole ring, imidazole ring, oxadiazole ring, thiadiazole ring, triazole ring, tetrazole ring, pyrazole ring, and pyridine. ring, pyrimidine ring, pyridazine ring, pyrazine ring, triazine ring, indole ring, isoindole ring, 1H-indazole ring, benzimidazole ring, benzoxazole ring, benzothiazole ring, 1H-benzotriazole ring, quinoline ring, isoquinoline ring, Cinnoline ring, quinazoline ring, quinoxaline ring, phenanthroline ring, phthalazine ring, naphthyridine ring, purine ring, pteridine ring, carbazole ring, acridine ring, phenoxathiine ring, phenoxazine ring, phenothiazine ring, phenazine ring, phenazacillin ring, indolizine ring, furan ring, benzofuran ring, isobenzofuran ring, dibenzofuran ring, naphthobenzofuran ring, thiophene ring, benzothiophene ring, isobenzothiophene ring, dibenzothiophene ring, naphthobenzothiophene ring, benzophosphole ring, dibenzophosphole ring, These include a benzophosphole oxide ring, a dibenzophosphole oxide ring, a furazane ring, a thianthrene ring, an indolocarbazole ring, a benziindolocarbazole ring, a benzobenzoindolocarbazole ring, an imidazoline ring, and an oxazoline ring.

"Aryl" is, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 20 carbon atoms, aryl having 6 to 16 carbon atoms, aryl having 6 to 12 carbon atoms, or aryl having 6 to 10 carbon atoms. Such as aryl.
Specific "aryl" includes, for example, phenyl which is a monocyclic system, biphenylyl (2-biphenylyl, 3-biphenylyl, or 4-biphenylyl) which is a bicyclic system, naphthyl (1-naphthyl or 2-naphthyl), tricyclic terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'- yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o -terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, or p-terphenyl- acenaphthylene-(1-, 3-, 4-, or 5-yl), fluorene-(1-, 2-, 3-, 4-, or 9-)yl, which is a fused tricyclic ring system , phenalen-(1- or 2-)yl, or phenanthrene-(1-, 2-, 3-, 4-, or 9-)yl, quaterphenylyl (5'-phenyl-m -terphenyl-2-yl, 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, or m-quaterphenyl), a fused tetracyclic ring system , triphenylene-(1- or 2-)yl, pyren-(1-, 2-, or 4-)yl, or naphthacen-(1-, 2-, or 5-)yl, or a fused pentacyclic ring system. perylene-(1-, 2-, or 3-)yl, or pentacen-(1-, 2-, 5-, or 6-)yl.

"Arylene" is, for example, arylene having 6 to 30 carbon atoms, preferably arylene having 6 to 20 carbon atoms, arylene having 6 to 16 carbon atoms, arylene having 6 to 12 carbon atoms, or arylene having 6 to 10 carbon atoms. Such as Arilene.
Specific examples of "arylene" include a structure in which one hydrogen is removed from the above-mentioned "aryl" (monovalent group) to make it a divalent group.

"Heteroaryl" is, for example, a heteroaryl having 2 to 30 carbon atoms, preferably a heteroaryl having 2 to 25 carbon atoms, a heteroaryl having 2 to 20 carbon atoms, a heteroaryl having 2 to 15 carbon atoms, or a heteroaryl having 2 to 15 carbon atoms. Such as a heteroaryl having a number of 2 to 10. Further, "heteroaryl" is a monovalent group such as a heterocycle containing, for example, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.
Specific examples of "heteroaryl" include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H- indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phenanthrolinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiinyl, Phenoxazinyl, phenothiazinyl, phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, isobenzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzo Phosphoryl, dibenzophosphoryl, monovalent group of benzophosphor oxide ring, monovalent group of dibenzophosphor oxide ring, furazanil, thianthrenyl, indolocarbazolyl, benziindrocarbazolyl, benzobenzoindrocarbazolyl, These include imidazolinyl, oxazolinyl, or dibenzosilacyclopentadienyl.

"Heteroarylene" is, for example, heteroarylene having 2 to 30 carbon atoms, preferably heteroarylene having 2 to 25 carbon atoms, heteroarylene having 2 to 20 carbon atoms, heteroarylene having 2 to 15 carbon atoms, or carbon Examples include heteroarylene of numbers 2 to 10. Further, "heteroarylene" is a divalent group such as a heterocycle containing, for example, 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.
Specific examples of "heteroarylene" include a structure in which one hydrogen is removed from the above-mentioned "heteroaryl" (monovalent group) to make it a divalent group.

"Diarylamino" is an amino group substituted with two aryls, and the above explanation of "aryl" can be cited for details of this aryl.
"Diheteroarylamino" is an amino group substituted with two heteroaryls, and for details of this heteroaryl, the above explanation of "heteroaryl" can be cited.
"Arylheteroarylamino" is an amino group substituted with aryl and heteroaryl, and the above explanation of "aryl" and "heteroaryl" can be cited for details of this aryl and heteroaryl.

"Diarylboryl" is a boryl group substituted with two aryls, and the above explanation of "aryl" can be cited for details of this aryl. In addition, these two aryls may be a single bond or a connecting group (for example, -CH ₂ -CH ₂ -, -CHR-CHR-, -CR ₂ -CR ₂ -, -CH=CH-, -CR=CR-, -C≡C-, >N-R, >O, >S, >C(-R) ₂ , >Si(-R) ₂ , or >Se). Here, R of -CHR-CHR-, R of -CR ₂ -CR ₂ -, R of -CR=CR-, R of >N-R, R of >C(-R) ₂ , and >Si R in (-R) is aryl, heteroaryl, diarylamino, alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, or aryloxy, and at least one hydrogen in R is further aryl, heteroaryl, alkyl, May be substituted with alkenyl, alkynyl, or cycloalkyl. Furthermore, two adjacent R's may form a ring to form cycloalkylene, arylene, or heteroarylene. For details of the substituents listed here, please refer to the explanations of "aryl", "arylene", "heteroaryl", "heteroarylene", and "diarylamino" mentioned above, as well as the "alkyl" and "alkenyl" mentioned below. , "alkynyl", "cycloalkyl", "cycloalkylene", "alkoxy", and "aryloxy" may be cited.

"Alkyl" may be either straight chain or branched chain, for example, straight chain alkyl having 1 to 24 carbon atoms or branched chain alkyl having 3 to 24 carbon atoms, preferably alkyl having 1 to 18 carbon atoms (carbon Branched chain alkyl having 3 to 18 carbon atoms), alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms), alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms), carbon number These include alkyl having 1 to 5 carbon atoms (branched alkyl having 3 to 5 carbon atoms), alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms), and the like.
Specific "alkyl" includes, for example, methyl, ethyl, n-propyl, isopropyl, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1,2-trimethylpropyl, 1,1,2 , 2-tetramethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, n-butyl, isobutyl, s-butyl, t-butyl, 2-ethylbutyl, 1,1-dimethylbutyl, 3,3-dimethyl Butyl, 1,1-diethylbutyl, 1-ethyl-1-methylbutyl, 1-propyl-1-methylbutyl, 1,1,3-trimethylbutyl, 1-ethyl-1,3-dimethylbutyl, n-pentyl, isopentyl , neopentyl, t-pentyl (t-amyl), 1-methylpentyl, 2-propylpentyl, 1,1-dimethylpentyl, 1-ethyl-1-methylpentyl, 1-propyl-1-methylpentyl, 1-butyl -1-methylpentyl, 1,1,4-trimethylpentyl, n-hexyl, 1-methylhexyl, 2-ethylhexyl, 1,1-dimethylhexyl, 1-ethyl-1-methylhexyl, 1,1,5- Trimethylhexyl, 3,5,5-trimethylhexyl, n-heptyl, 1-methylheptyl, 1-hexylheptyl, 1,1-dimethylheptyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1,1-dimethyloctyl, n-nonyl, n-decyl, 1-methyldecyl, n-undecyl, n-dodecyl, n- Examples include tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, and n-eicosyl.

Regarding "alkenyl", the above explanation of "alkyl" can be referred to, and it is a group in which the C-C single bond in the structure of "alkyl" is replaced with a C=C double bond, and only one It also includes groups in which two or more single bonds are substituted with double bonds (also called alkadien-yl or alkatrien-yl).

Regarding "alkynyl", the above explanation of "alkyl" can be referred to, and it is a group in which the C-C single bond in the "alkyl" structure is replaced with a C≡C triple bond, and only one is required. It also includes groups in which two or more single bonds are substituted with triple bonds (also called alkadiin-yl or alkatriin-yl).

"Cycloalkyl" is, for example, cycloalkyl having 3 to 24 carbon atoms, preferably cycloalkyl having 3 to 20 carbon atoms, cycloalkyl having 3 to 16 carbon atoms, cycloalkyl having 3 to 14 carbon atoms, or cycloalkyl having 3 to 14 carbon atoms. Examples include cycloalkyl having 3 to 12 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, and cycloalkyl having 5 carbon atoms.
Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, or alkyls thereof having 1 to 5 carbon atoms or 1 to 4 carbon atoms (especially methyl). Substituted product, norbornenyl, bicyclo[1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1 .0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, or decahydroazulenyl.

"Cycloalkylene" is, for example, cycloalkylene having 3 to 24 carbon atoms, preferably cycloalkylene having 3 to 20 carbon atoms, cycloalkylene having 3 to 16 carbon atoms, cycloalkylene having 3 to 14 carbon atoms, or cycloalkylene having 3 to 14 carbon atoms. Examples include cycloalkylene having 3 to 12 carbon atoms, cycloalkylene having 5 to 10 carbon atoms, cycloalkylene having 5 to 8 carbon atoms, cycloalkylene having 5 to 6 carbon atoms, and cycloalkylene having 5 carbon atoms.
Specific examples of "cycloalkylene" include a structure in which one hydrogen is removed from the above-mentioned "cycloalkyl" (monovalent group) to make it a divalent group.

"Alkoxy" may be either straight chain or branched chain, for example, straight chain alkoxy having 1 to 24 carbon atoms or branched chain alkoxy having 3 to 24 carbon atoms, preferably alkoxy having 1 to 18 carbon atoms (carbon Branched chain alkoxy having 3 to 18 carbon atoms), alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 12 carbon atoms), alkoxy having 1 to 6 carbon atoms (branched alkoxy having 3 to 6 carbon atoms), carbon number These include alkoxy having 1 to 5 carbon atoms (branched alkoxy having 3 to 5 carbon atoms), alkoxy having 1 to 4 carbon atoms (branched alkoxy having 3 to 4 carbon atoms), and the like.
Specific "alkoxy" includes, for example, methoxy, ethoxy, n-propoxy, isopropoxy, 1-ethyl-1-methylpropoxy, 1,1-diethylpropoxy, 1,1,2-trimethylpropoxy, 1,1, 2,2-tetramethylpropoxy, 1-ethyl-1,2,2-trimethylpropoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy, 2-ethylbutoxy, 1,1-dimethylbutoxy, 3,3 -dimethylbutoxy, 1,1-diethylbutoxy, 1-ethyl-1-methylbutoxy, 1-propyl-1-methylbutoxy, 1,1,3-trimethylbutoxy, 1-ethyl-1,3-dimethylbutoxy, n -Pentyloxy, isopentyloxy, neopentyloxy, t-pentyloxy (t-amyloxy), 1-methylpentyloxy, 2-propylpentyloxy, 1,1-dimethylpentyloxy, 1-ethyl-1-methylpentyl Oxy, 1-propyl-1-methylpentyloxy, 1-butyl-1-methylpentyloxy, 1,1,4-trimethylpentyloxy, n-hexyloxy, 1-methylhexyloxy, 2-ethylhexyloxy, 1, 1-dimethylhexyloxy, 1-ethyl-1-methylhexyloxy, 1,1,5-trimethylhexyloxy, 3,5,5-trimethylhexyloxy, n-heptyloxy, 1-methylheptyloxy, 1-hexyl heptyloxy, 1,1-dimethylheptyloxy, 2,2-dimethylheptyloxy, 2,6-dimethyl-4-heptyloxy, n-octyloxy, t-octyloxy (1,1,3,3-tetramethyl butyloxy), 1,1-dimethyloctyloxy, n-nonyloxy, n-decyloxy, 1-methyldecyloxy, n-undecyloxy, n-dodecyloxy, n-tridecyloxy, n-tetradecyloxy, n -pentadecyloxy, n-hexadecyloxy, n-heptadecyloxy, n-octadecyloxy, or n-eicosyloxy.

"Aryloxy" is a group represented by "Ar--O-- (Ar is an aryl group)", and for details of this aryl, the above explanation of "aryl" can be cited.

"Substituted silyl" is, for example, silyl substituted with at least one of aryl, alkyl, and cycloalkyl, preferably triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, or alkyl It is dicycloalkylsilyl.

"Triarylsilyl" is a silyl group substituted with three aryls, and the above explanation of "aryl" can be cited for details of this aryl.
Specific examples of "triarylsilyl" include triphenylsilyl, diphenylmononaphthylsilyl, monophenyldinaphthylsilyl, and trinaphthylsilyl.

"Trialkylsilyl" is a silyl group substituted with three alkyl groups, and for details of this alkyl, the above explanation of "alkyl" can be cited.
Specific "trialkylsilyl" includes, for example, trimethylsilyl, triethylsilyl, tri-n-propylsilyl, triisopropylsilyl, tri-n-butylsilyl, triisobutylsilyl, tri-s-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, n-Propyldimethylsilyl, isopropyldimethylsilyl, n-butyldimethylsilyl, isobutyldimethylsilyl, s-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, n-propyldiethylsilyl, isopropyldiethylsilyl, n-butyldiethyl Silyl, s-butyldiethylsilyl, t-butyldiethylsilyl, methyldi-n-propylsilyl, ethyldi-n-propylsilyl, n-butyldi-n-propylsilyl, s-butyldi-n-propylsilyl, t-butyldi-n-propylsilyl, Examples include methyldiisopropylsilyl, ethyldiisopropylsilyl, n-butyldiisopropylsilyl, s-butyldiisopropylsilyl, and t-butyldiisopropylsilyl.

"Tricycloalkylsilyl" is a silyl group substituted with three cycloalkyl groups, and for details of this cycloalkyl, the above explanation of "cycloalkyl" can be cited.
Specific examples of "tricycloalkylsilyl" include tricyclopentylsilyl and tricyclohexylsilyl.

"Dialkylcycloalkylsilyl" is a silyl group substituted with two alkyls and one cycloalkyl, and the above explanation of "alkyl" and "cycloalkyl" can be cited for details of this alkyl and cycloalkyl.

"Alkyldicycloalkylsilyl" is a silyl group substituted with one alkyl and two cycloalkyl, and the above explanation of "alkyl" and "cycloalkyl" can be cited for details of this alkyl and cycloalkyl. .

"Linking group" refers to -CH ₂ -CH ₂ -, -CHR-CHR-, -CR ₂ -CR ₂ -, -CH=CH-, -CR=CR-, -C≡C-, -N(- R)-, -O-, -S-, -C(-R) ₂ -, -Si(-R) ₂ -, -C(=O)-, -C(=S)-, -P(= O)-, -P(=S)-, -S(=O)-, -S(=O) ₂ -, and -Se-. Among these, the linking group is preferably -CR=CR-, -N(-R)-, -O-, -S-, and -C(-R) ₂ -, and -CR=CR-, -N( -R)-, -O-, and -S- are more preferred. In addition, the above "-CHR-CHR-", "-CR ₂ -CR ₂ -", "-CR=CR-", "-N(-R)-", "-C(-R) _2- ", and R in "-Si(-R) _2- " is each independently hydrogen, aryl, heteroaryl, alkyl, alkenyl, alkynyl, or cycloalkyl, and at least one hydrogen in R is alkyl or cycloalkyl. Optionally substituted with alkyl. Furthermore, two adjacent R's may form a ring to form cycloalkylene, arylene, or heteroarylene.

Substituents affect the emission wavelength of polycyclic aromatic compounds due to the steric hindrance, electron donating, and electron withdrawing properties of their structures, so the emission wavelength can be adjusted by selecting the substituent. . Preferably it is a group represented by the following structural formula, more preferably methyl, t-butyl, bicyclooctyl, cyclohexyl, adamantyl, phenyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5 -xylyl, 2,6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, diphenylboryl, dimesitylboryl, dibenzoxaborinyl, phenyl Dibenzodiborininyl, carbazolyl, 3,6-dimethylcarbazolyl, 3,6-di-t-butylcarbazolyl and phenoxy, more preferably methyl, t-butyl, phenyl, o-tolyl, 2 , 6-xylyl, 2,4,6-mesityl, diphenylamino, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, carbazolyl, 3,6-dimethylcarbazolyl and 3,6- It is di-t-butylcarbazolyl. From the viewpoint of ease of synthesis, those with greater steric hindrance are preferable for selective synthesis; specifically, t-butyl, o-tolyl, p-tolyl, 2,4-xylyl, 2,5 -xylyl, 2,6-xylyl, 2,4,6-mesityl, di-p-tolylamino, bis(p-(t-butyl)phenyl)amino, 3,6-dimethylcarbazolyl, 3,6-dimethyl -t-butylcarbazolyl and tribenzazepinyl are preferred.

In the structural formula below, "Me" represents methyl, "tBu" represents t-butyl, "tAm" represents t-amyl, "tOct" represents t-octyl, and * represents the bonding position.

<Explanation of cycloalkane condensation>
Further, at least one of the aromatic ring and the heteroaromatic ring in the chemical structure of the polycyclic aromatic compound of the present invention may be fused with at least one cycloalkane.

For example, at least one of the a-ring, b-ring, c-ring, d-ring, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl may be fused with at least one cycloalkane.

"Cycloalkanes" include cycloalkanes with 3 to 24 carbon atoms, cycloalkanes with 3 to 20 carbon atoms, cycloalkanes with 3 to 16 carbon atoms, cycloalkanes with 3 to 14 carbon atoms, and cycloalkanes with 5 to 10 carbon atoms. Examples include alkanes, cycloalkanes having 5 to 8 carbon atoms, cycloalkanes having 5 to 6 carbon atoms, and cycloalkanes having 5 carbon atoms.

Specific cycloalkanes include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, norbornene, bicyclo[1.1.0]butane, bicyclo[1.1.1]pentane, Bicyclo[2.1.0]pentane, bicyclo[2.1.1]hexane, bicyclo[3.1.0]hexane, bicyclo[2.2.1]heptane, bicyclo[2.2.2]octane, Examples include adamantane, diamantane, decahydronaphthalene and decahydroazulene, as well as alkyl (especially methyl) substituted products having 1 to 5 carbon atoms, halogen (especially fluorine) substituted products and deuterium substituted products thereof.

Among these, at least one carbon at the α-position of a cycloalkane (in a cycloalkyl condensed to an aromatic ring or a heteroaromatic ring, the carbon at the position adjacent to the carbon at the condensation site) as shown in the structural formula below, for example. A structure in which one hydrogen is substituted is preferable, a structure in which two hydrogens are substituted at the α-position carbon is more preferable, and a structure in which a total of four hydrogens are substituted at two α-position carbons is even more preferable. Examples of the substituent include an alkyl (especially methyl) substituent having 1 to 5 carbon atoms, a halogen (especially fluorine) substituent, and a deuterium substituent.

The number of cycloalkanes fused to one aromatic ring or heteroaromatic ring is preferably 1 to 3, more preferably 1 or 2, and even more preferably 1. For example, an example in which one or more cycloalkanes are condensed to one benzene ring (phenyl group) is shown below. In each structural formula, * means a benzene ring included in the skeletal structure of the compound when it is a benzene ring, and a bond substituted in the skeletal structure of the compound when it is a phenyl group. Condensed cycloalkanes as shown in formula (Cy-1-4) and formula (Cy-2-4) may be condensed with each other. Even if the ring (group) to be condensed is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl group), if the cycloalkane to be condensed is another cycloalkane other than cyclopentane or cyclohexane The same is true even if

At least one -CH ₂ - in the cycloalkane may be substituted with -O-. However, when multiple -CH ₂ - groups are substituted with -O-, adjacent -CH ₂ - groups are not replaced with -O-. For example, an example in which one or more -CH ₂ - in a cycloalkane fused to one benzene ring (phenyl group) is substituted with -O- is shown below. In each structural formula, * means a benzene ring included in the skeletal structure of the compound when it is a benzene ring, and means a bond substituted in the skeletal structure of the compound when it is a phenyl group. Even if the ring (group) to be condensed is an aromatic ring or heteroaromatic ring other than a benzene ring (phenyl group), if the cycloalkane to be condensed is another cycloalkane other than cyclopentane or cyclohexane The same is true even if

At least one hydrogen in the cycloalkane may be substituted, and examples of this substituent include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, and diarylboryl (two aryls are a single bond). or may be bonded via a linking group), alkyl, cycloalkyl, alkoxy, aryloxy, substituted silyl, deuterium, cyano, or halogen, and for details, refer to the explanation of the substituents above. can do. Among these substituents, alkyl (eg, alkyl having 1 to 6 carbon atoms), cycloalkyl (eg, cycloalkyl having 3 to 14 carbon atoms), halogen (eg, fluorine), deuterium, and the like are preferred. In addition, when cycloalkyl is substituted, a substitution form forming a spiro structure may be used. For example, an example in which a spiro structure is formed in a cycloalkane condensed to one benzene ring (phenyl group) is shown below. In each structural formula, * means a benzene ring included in the skeletal structure of the compound when it is a benzene ring, and a bond substituted in the skeletal structure of the compound when it is a phenyl group.

As another form of cycloalkane condensation, a polycyclic aromatic compound represented by formula (1) or formula (2) is, for example, a diarylamino group condensed with a cycloalkane (condensed to this aryl group moiety), Examples include substitution with a carbazolyl group condensed with a cycloalkane (condensed to this benzene ring moiety) or a benzocarbazolyl group condensed with a cycloalkane (condensed to this benzene ring moiety). Examples of the "diarylamino group" include the groups explained above as the "substituent".

Further, as a more specific example, R ⁴ in the polycyclic aromatic compound represented by formula (1) or formula (2) is a diarylamino group condensed with a cycloalkane (condensed to this aryl group moiety). Alternatively, an example is a carbazolyl group fused with a cycloalkane (fused to this benzene ring part).

<Explanation of substitution with deuterium, cyano, or halogen>
At least one hydrogen in the polycyclic aromatic compound of the present invention may be substituted with deuterium, cyano, or halogen. Halogen is fluorine, chlorine, bromine, or iodine, preferably fluorine, chlorine, or bromine, and more preferably fluorine or chlorine.

<Description of specific examples of the polycyclic aromatic compound of the present invention>
More specific examples of polycyclic aromatic compounds include compounds represented by the following structural formula. In addition, "Me" in the following structural formula represents a methyl group, and "tBu" represents a t-butyl group.

<Explanation of increasing the molecular weight of polycyclic aromatic compounds>
The polycyclic aromatic compound represented by the above general formula (1) or general formula (2) is a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer (this polymer (the monomer for obtaining the compound has a polymerizable substituent), or a polymer crosslinked product obtained by further crosslinking the polymer compound (the polymer compound for obtaining the polymer crosslinked product has a crosslinkable substituent) ), or a pendant polymer compound obtained by reacting a main chain polymer with the reactive compound (the reactive compound to obtain the pendant polymer compound has a reactive substituent), or It can also be used as a pendant-type crosslinked polymer obtained by further crosslinking the pendant-type polymer compound (the pendant-type polymer compound for obtaining this pendant-type crosslinked polymer has a crosslinkable substituent) as a material for organic devices. For example, it can be used in materials for organic electroluminescent devices, materials for organic field effect transistors, materials for organic thin film solar cells, or wavelength conversion filters.

The above-mentioned reactive substituents (including the polymerizable substituents, the crosslinkable substituents, and the reactive substituents for obtaining a pendant polymer, hereinafter also simply referred to as "reactive substituents") are: , a substituent that can increase the molecular weight of the polycyclic aromatic compound, a substituent that can further crosslink the polymer compound thus obtained, and a substituent that can react pendantly to the main chain polymer. Although not particularly limited, substituents having the following structures are preferred. * in each structural formula indicates the bonding position.

L is each independently a single bond, -O-, -S-, >C=O, -OC(=O)-, alkylene having 1 to 12 carbon atoms, oxyalkylene having 1 to 12 carbon atoms and polyoxyalkylene having 1 to 12 carbon atoms. Among the above substituents, those represented by formula (XLS-1), formula (XLS-2), formula (XLS-3), formula (XLS-9), formula (XLS-10) or formula (XLS-17) are A group represented by formula (XLS-1), formula (XLS-3) or formula (XLS-17) is more preferred.

Such polymer compounds, crosslinked polymers, pendant polymer compounds, and pendant crosslinked polymers contain, in addition to the repeating unit of the polycyclic aromatic compound represented by formula (1) or formula (2). Substituted or unsubstituted triarylamine, substituted or unsubstituted fluorene, substituted or unsubstituted anthracene, substituted or unsubstituted tetracene, substituted or unsubstituted triazine, substituted or unsubstituted carbazole, substituted or unsubstituted containing as a repeating unit at least one selected from the group consisting of tetraphenylsilane, substituted or unsubstituted spirofluorene, substituted or unsubstituted triphenylphosphine, substituted or unsubstituted dibenzothiophene, and substituted or unsubstituted dibenzofuran. But that's fine.
Substituents in these repeating units include, for example, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (even if two aryls are bonded via a single bond or a linking group). Examples include alkyl, cycloalkyl, alkoxy, aryloxy, triarylsilyl, trialkylsilyl, tricycloalkylsilyl, dialkylcycloalkylsilyl, and alkyldicycloalkylsilyl. For details of the "aryl" of triarylamine and these substituents, the explanation for the polycyclic aromatic compound represented by formula (1) or formula (2) can be cited.

Details of the uses of such polymer compounds, crosslinked polymers, pendant polymer compounds, and pendant crosslinked polymers (hereinafter also simply referred to as "polymer compounds and crosslinked polymers") will be described later.

2. Method for producing polycyclic aromatic compounds The polycyclic aromatic compounds represented by formulas (1) and (2) are basically produced by first preparing a ring, b ring, c ring, d ring, and e ring. An intermediate is produced by bonding the condensed rings containing with a bonding group (group containing X) (first reaction), and then a condensed ring containing The final product can be produced by linking the rings with a linking group (Y-containing group) (second reaction). The manufacturing method described in International Publication No. 2015/102118 and International Publication No. 2021/230133 can be referred to.

For the first reaction, for example, a general reaction such as a nucleophilic substitution reaction or an Ullmann reaction can be used for an etherification reaction, and a general reaction such as a Buchwald-Hartwig reaction can be used for an amination reaction. Further, in the second reaction, a tandem hetero Friedel-Crafts reaction (continuous aromatic electrophilic substitution reaction, the same applies hereinafter) can be used.

The second reaction is a reaction in which Y is introduced to bond a condensed ring including ring a, ring b, ring c, ring d, and ring e, as shown in schemes (1) and (2) below. By reacting a Y halide such as boron trichloride or boron tribromide with the precursor, a tandem Bora-Friedel-Crafts reaction can be carried out to obtain the desired product. In order to accelerate the reaction, a Lewis acid such as aluminum trichloride or a Brønsted base such as N,N-diisopropylethylamine may be added.

By appropriately selecting the raw materials to be used, a polycyclic aromatic compound having a substituent at a desired position can be synthesized.

Specific examples of the solvent used in the above reaction include t-butylbenzene and xylene.

In addition, in the synthesis methods of schemes (1) and (2) above, Y was introduced by adding a halide of Y such as boron trichloride or boron tribromide to the precursor, but After halogen-metal exchange of a compound in which hydrogen atoms have become halogen atoms with n-butyllithium, sec-butyllithium, t-butyllithium, etc., Y halides such as boron trichloride and boron tribromide are exchanged. In addition, after performing lithium-boron metal exchange, a Brønsted base such as N,N-diisopropylethylamine is added to cause a tandem Bora-Friedel-Crafts reaction to obtain the desired product.

The orthometalation reagents used in the above schemes (1) and (2) include alkyllithiums such as methyllithium, n-butyllithium, sec-butyllithium, and t-butyllithium, lithium diisopropylamide, and lithium tetramethyl. Examples include organic alkali metal compounds such as piperidide, lithium hexamethyldisilazide, and potassium hexamethyldisilazide.

The metal-Y metal exchange reagents used in the above schemes (1) and (2) include Y trifluoride, Y trichloride, Y tribromide, Y triiodide, etc. Examples include halides, aminated halides of Y such as CIPN(NEt ₂ ) ₂ , alkoxylated Y, and aryloxylated Y. Examples of the metal-boron metal exchange reagent include boron halides such as boron trifluoride, boron trichloride, boron tribromide, and boron triiodide, boron alkoxides, and aryl oxides of boron.

The Brønsted bases used in the above schemes (1) and (2) include N,N-diisopropylethylamine, triethylamine, 2,2,6,6-tetramethylpiperidine, 1,2,2,6,6 -Pentamethylpiperidine, N,N-dimethylaniline, N,N-dimethyltoluidine, 2,6-lutidine, sodium tetraphenylborate, potassium tetraphenylborate, triphenylborane, tetraphenylsilane, Ar ₄ BNa, Ar ₄ BK, Ar ₃ B, Ar ₄ Si (Ar is aryl such as phenyl), and the like.

The Lewis acids used in the above schemes (1) and (2) include AlCl ₃ , AlBr ₃ , AlF ₃ , BF ₃ .OEt ₂ , BCl ₃ , BBr ₃ , GaCl ₃ , GaBr ₃ , InCl ₃ , InBr ₃ , In(OTf) ₃ , SnCl ₄ , SnBr ₄ , AgOTf, ScCl ₃ , Sc(OTf) ₃ , ZnCl ₂ , ZnBr ₂ , Zn(OTf) ₂ , MgCl ₂ , MgBr ₂ , Mg(OTf) ₂ , LiOTf, NaO Tf , KOTF, Me ₃ SIOTF, CU (OTF) ₂ , CUCL ₂ , YCL 2, YCL ₃ , Y (OTF) ₃ , TICL ₄ , TICL ₄ , ZRCL 4, ZRCL ₄ , ZRCL ₄ , FECL 3, COCL ₃ , COCL ₃ , COCL 3, COCL ₃ , COBR _3, etc. can give.

In schemes (1) and (2) above, a Brønsted base or a Lewis acid may be used to promote the tandem hetero Friedel-Crafts reaction. However, when using Y halides such as Y trifluoride, Y trichloride, Y tribromide, and Y triiodide, as the aromatic electrophilic substitution reaction progresses, hydrogen fluoride, Since acids such as hydrogen chloride, hydrogen bromide, and hydrogen iodide are produced, it is effective to use a Brønsted base to scavenge the acids. On the other hand, when an aminated halide of Y or an alkoxylate of Y is used, it is often not necessary to use a Brønsted base because amines and alcohols are generated as the aromatic electrophilic substitution reaction progresses. However, since the elimination ability of amino and alkoxy is low, it is effective to use a Lewis acid that promotes their elimination.

Furthermore, the polycyclic aromatic compounds of the present invention include those in which at least some of the hydrogen atoms are substituted with deuterium or those in which halogens such as fluorine and chlorine are substituted; however, such compounds etc. can be synthesized in the same manner as above by using raw materials that are deuterated, fluorinated, or chlorinated at desired locations.

3. Organic Device In the chemical structural formulas exemplified below, "Me" represents a methyl group, and "tBu" represents a t-butyl group.
The polycyclic aromatic compound according to the present invention can be used as a material for organic devices. Examples of the organic device include an organic electroluminescent element, an organic field effect transistor, an organic thin film solar cell, and a wavelength conversion filter.

3-1. Organic electroluminescent device The polycyclic aromatic compound according to the present invention can be used, for example, as a material for an organic electroluminescent device. Below, the organic EL element according to this embodiment will be described in detail based on the drawings. FIG. 1 is a schematic cross-sectional view showing an organic EL element according to this embodiment.

<Structure of organic electroluminescent device>
The organic EL element 100 shown in FIG. 1 includes a substrate 101, an anode 102 provided on the substrate 101, a hole injection layer 103 provided on the anode 102, and a A hole transport layer 104 provided, a light emitting layer 105 provided on the hole transport layer 104, an electron transport layer 106 provided on the light emitting layer 105, and a light emitting layer 105 provided on the electron transport layer 106. It has an electron injection layer 107 and a cathode 108 provided on the electron injection layer 107.

Note that the organic EL element 100 can be manufactured in the reverse order, for example, by forming a substrate 101, a cathode 108 provided on the substrate 101, an electron injection layer 107 provided on the cathode 108, and an electron injection layer 107. an electron transport layer 106 provided on the electron transport layer 106; a light emitting layer 105 provided on the electron transport layer 106; a hole transport layer 104 provided on the light emitting layer 105; It is also possible to have a configuration including a hole injection layer 103 provided on the hole injection layer 103 and an anode 102 provided on the hole injection layer 103.

All of the above layers are not indispensable, and the minimum structural unit is the anode 102, the light emitting layer 105, and the cathode 108. Layer 107 is an optional layer. Moreover, each of the above layers may be composed of a single layer or a plurality of layers.

In addition to the above-mentioned configuration of "substrate/anode/hole injection layer/hole transport layer/light emitting layer/electron transport layer/electron injection layer/cathode", examples of the layers constituting the organic EL element include " "Substrate/Anode/Hole transport layer/Light emitting layer/Electron transport layer/Electron injection layer/Cathode", "Substrate/Anode/Hole injection layer/Light emitting layer/Electron transport layer/Electron injection layer/Cathode", "Substrate/ Anode / hole injection layer / hole transport layer / light emitting layer / electron injection layer / cathode", "substrate / anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode", "substrate / Anode/Emissive layer/Electron transport layer/Electron injecting layer/Cathode", "Substrate/Anode/Hole transport layer/Emissive layer/Electron injecting layer/Cathode", "Substrate/Anode/Hole transport layer/Emissive layer/Electron "Transport layer/Cathode", "Substrate/Anode/Hole injection layer/Light emitting layer/Electron injection layer/Cathode", "Substrate/Anode/Hole injection layer/Light emitting layer/Electron transport layer/Cathode", "Substrate/Anode" /light emitting layer/electron transport layer/cathode" or "substrate/anode/light emitting layer/electron injection layer/cathode" may be used.

<Substrate in organic electroluminescent device>
The substrate 101 is a support for the organic EL element 100, and is usually made of quartz, glass, metal, plastic, or the like. The substrate 101 is formed into a plate shape, a film shape, or a sheet shape depending on the purpose. For example, a glass plate, a metal plate, a metal foil, a plastic film, a plastic sheet, etc. are used. Among these, glass plates and plates made of transparent synthetic resins such as polyester, polymethacrylate, polycarbonate, and polysulfone are preferred. If it is a glass substrate, soda lime glass or non-alkali glass may be used, and the thickness may be sufficient to maintain mechanical strength, for example, 0.2 mm or more. The upper limit of the thickness is, for example, 2 mm or less, preferably 1 mm or less. Regarding the material of the glass, alkali-free glass is preferable because fewer ions elute from the glass, but soda lime glass coated with a barrier coating such as SiO ₂ is also commercially available, so it is recommended to use this. can. In addition, the substrate 101 may be provided with a gas barrier film such as a dense silicon oxide film on at least one side of the substrate 101 in order to improve gas barrier properties. In particular, a synthetic resin plate, film, or sheet with low gas barrier properties may be used as the substrate 101. When used, it is preferable to provide a gas barrier film.

<Anode in organic electroluminescent device>
The anode 102 plays the role of injecting holes into the light emitting layer 105. Note that when at least one of the hole injection layer 103 and the hole transport layer 104 is provided between the anode 102 and the light emitting layer 105, holes are injected into the light emitting layer 105 through these layers. It turns out.

Materials forming the anode 102 include inorganic compounds and organic compounds. Examples of inorganic compounds include metals (aluminum, gold, silver, nickel, palladium, chromium, etc.), metal oxides (indium oxide, tin oxide, indium-tin oxide (ITO), indium-zinc oxide, etc.). (IZO, etc.), metal halides (copper iodide, etc.), copper sulfide, carbon black, ITO glass, Nesa glass, etc. Examples of the organic compound include polythiophenes such as poly(3-methylthiophene), conductive polymers such as polypyrrole, and polyaniline. In addition, materials that are used as anodes for organic EL devices may be selected as appropriate.

The resistance of the transparent electrode is not limited as long as it can supply sufficient current for light emission of the light emitting element, but from the viewpoint of power consumption of the light emitting element, it is desirable that the resistance be low. For example, an ITO substrate with a resistance of 300 Ω/□ or less can function as an element electrode, but since it is now possible to supply substrates with a resistance of about 10 Ω/□, for example, 100 to 5 Ω/□, preferably 50 to 5 Ω. It is particularly desirable to use a low resistance product with /□. The thickness of ITO can be arbitrarily selected according to the resistance value, but it is usually used between 50 and 300 nm.

<Hole injection layer and hole transport layer in organic electroluminescent device>
The hole injection layer 103 plays a role of efficiently injecting holes moving from the anode 102 into the light emitting layer 105 or the hole transport layer 104. The hole transport layer 104 plays a role of efficiently transporting holes injected from the anode 102 or holes injected from the anode 102 via the hole injection layer 103 to the light emitting layer 105. The hole injection layer 103 and the hole transport layer 104 are each formed by laminating and mixing one or more hole injection/transport materials, or by a mixture of a hole injection/transport material and a polymer binder. be done. Alternatively, the layer may be formed by adding an inorganic salt such as iron(III) chloride to the hole injection/transport material.

As a hole injection/transport material, it is necessary to efficiently inject and transport holes from the positive electrode between the electrodes where an electric field is applied, and the material has high hole injection efficiency and efficiently transports the injected holes. It is desirable to do so. For this purpose, it is preferable to use a substance that has a low ionization potential, high hole mobility, excellent stability, and does not easily generate trapping impurities during production and use.

As a material for forming the hole injection layer 103 and the hole transport layer 104, a polycyclic aromatic compound represented by the above general formula (1) or general formula (2) can be used. In addition, in photoconductive materials, compounds conventionally used as hole charge transport materials, p-type semiconductors, and known compounds used in hole injection layers and hole transport layers of organic EL devices. Any compound can be selected and used.

Specific examples thereof include carbazole derivatives (N-phenylcarbazole, polyvinylcarbazole, etc.), biscarbazole derivatives such as bis(N-arylcarbazole) or bis(N-alkylcarbazole), triarylamine derivatives (aromatic tertiary Polymer with amino in main chain or side chain, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4 ,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-dinaphthyl-4,4'-diaminobiphenyl, N,N'-diphenyl-N,N'-di(3-methylphenyl)-4 , 4'-diphenyl-1,1'-diamine, N,N'-dinaphthyl-N,N'-diphenyl-4,4'-diphenyl-1,1'-diamine, N ⁴ ,N ^4' -diphenyl- N ⁴ ,N ^4' -bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine, N ⁴ ,N ⁴ ,N ^4' ,N ^{4 '} -tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine, 4,4',4"-tris(3-methylphenyl(phenyl) ) triphenylamine derivatives such as (amino) triphenylamine, starburst amine derivatives, etc.), stilbene derivatives, phthalocyanine derivatives (metal-free, copper phthalocyanine, etc.), pyrazoline derivatives, hydrazone compounds, benzofuran derivatives and thiophene derivatives, oxadiazole derivatives, quinoxaline derivatives (for example, 1,4,5,8,9,12-hexaazatriphenylene-2,3,6,7,10,11-hexacarbonitrile, etc.), heterocyclic compounds such as porphyrin derivatives, polysilane Polycarbonate, styrene derivatives, polyvinylcarbazole, polysilane, etc., which have the above-mentioned monomers in their side chains, are preferable for polymer systems, but they can form a thin film necessary for manufacturing a light emitting device, and holes can be injected from the anode. , and is not particularly limited as long as it is a compound that can transport holes.

It is also known that the conductivity of organic semiconductors is strongly influenced by their doping. Such an organic semiconductor matrix material is composed of a compound with good electron donating properties or a compound with good electron accepting properties. For doping with electron donating substances, strong electron acceptors such as tetracyanoquinone dimethane (TCNQ) or 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4TCNQ) are known. (For example, the literature "M. Pfeiffer, A. Beyer, T. Fritz, K. Leo, Appl. Phys. Lett., 73(22), 3202-3204 (1998)" and the literature "J. Blochwitz, M. Pheiffer, T. Fritz, K. Leo, Appl. Phys. Lett., 73 (6), 729-731 (1998)). These generate so-called holes by electron transfer processes in electron-donating base materials (hole-transporting materials). Depending on the number and mobility of holes, the conductivity of the base material varies considerably. As matrix materials having hole transport properties, for example benzidine derivatives (TPD etc.) or starburst amine derivatives (TDATA etc.) or certain metal phthalocyanines (in particular zinc phthalocyanine (ZnPc) etc.) are known (especially Publication No. 2005-167175).

The hole injection layer material and the hole transport layer material described above are a polymer compound obtained by polymerizing a reactive compound substituted with a reactive substituent as a monomer, or a polymer crosslinked product thereof, or A pendant polymer compound obtained by reacting a main chain polymer with the above-mentioned reactive compound, or a pendant polymer crosslinked product thereof can also be used as a hole layer material. As for the reactive substituent in this case, the explanation for the polycyclic aromatic compound represented by formula (1) or formula (2) can be cited.
Details of the uses of such polymer compounds and crosslinked polymers will be described later.

<Light-emitting layer in organic electroluminescent device>
The light-emitting layer 105 is a layer that emits light by recombining holes injected from the anode 102 and electrons injected from the cathode 108 between the electrodes to which an electric field is applied. As a material for forming the light-emitting layer 105, a polycyclic aromatic compound represented by the above general formula (1) or general formula (2) can be used. In addition, any compound that emits light when excited by the recombination of holes and electrons (luminescent compound) is sufficient, can form a stable thin film shape, and has strong luminescence (fluorescence) efficiency in the solid state. Preferably, it is a compound shown in FIG.

The light-emitting layer may be a single layer or consist of multiple layers, and each is formed from a material for the light-emitting layer (host material, dopant material). The host material and the dopant material may each be one type or a combination of a plurality of types. Further, the host material may be mixed with a material for a hole transport layer or a material for an electron transport layer, or may be a combination thereof. The dopant material may be contained entirely or partially in the host material. As a doping method, it can be formed by a co-evaporation method with a host material, but it can also be formed by pre-mixing with the host material and then vapor-depositing at the same time, or by pre-mixing the host material with an organic solvent and then using a wet film-forming method. It may be coated with a film.

The amount of host material used varies depending on the type of host material, and may be determined depending on the characteristics of the host material. The amount of the host material to be used is preferably 50 to 99.999% by weight, more preferably 80 to 99.95% by weight, and even more preferably 90 to 99.9% by weight of the entire material for the light emitting layer. It is.

E _T1 of the host material is preferably 2.50 eV or more, more preferably 2.53 eV or more, and even more preferably 2.60 eV or more.

The amount of dopant material to be used varies depending on the type of dopant material, and may be determined according to the characteristics of the dopant material. The amount of the dopant to be used is preferably 0.001 to 50% by weight, more preferably 0.05 to 20% by weight, and even more preferably 0.1 to 10% by weight based on the entire material for the light emitting layer. be. The above range is preferable in that, for example, concentration quenching phenomenon can be prevented. Further, from the viewpoint of durability, it is also preferable that some or all of the hydrogen atoms in the dopant material are deuterated.

On the other hand, in an organic EL device using a thermally activated delayed fluorescence dopant material, it is preferable to use a low concentration of the dopant material in order to prevent the concentration quenching phenomenon; It is preferable from the viewpoint of the efficiency of the thermally activated delayed fluorescence mechanism. Furthermore, in an organic EL device using a thermally activated delayed fluorescence assist dopant material, in terms of efficiency of the thermally activated delayed fluorescence mechanism of the assist dopant material, the amount of dopant material used is smaller than the amount of assist dopant material used. It is preferable that the amount is low in concentration.

When an assist dopant material is used, the approximate usage amounts of the host material, assist dopant material, and dopant material are 40 to 99.999% by weight, 59 to 1% by weight, and 20 to 20% by weight, respectively, based on the total luminescent layer material. 0.001% by weight, preferably 60-99.99% by weight, 39-5% by weight and 10-0.01% by weight, more preferably 70-99.95% by weight, 29% by weight, respectively. -10% by weight and 5-0.05% by weight. The polycyclic aromatic compound represented by the above general formula (1) or general formula (2) can also be used as an assist dopant material.

Examples of host materials include fused ring derivatives such as anthracene, pyrene, dibenzochrysene, or fluorene, which have long been known as light emitters, bisstyryl derivatives such as bisstyrylanthracene derivatives and distyrylbenzene derivatives, tetraphenylbutadiene derivatives, and cyclopentadiene derivatives. Examples include. Particularly preferred are anthracene compounds, fluorene compounds, and dibenzochrysene compounds. Further, from the viewpoint of durability, it is also preferable that some or all of the hydrogen atoms in the host material are deuterated. Furthermore, it is also preferable to configure the light-emitting layer by combining a host compound in which some or all of the hydrogen atoms are deuterated and a dopant compound in which some or all of the hydrogen atoms are deuterated.

<Anthracene compound>
The anthracene compound as a host is, for example, a compound represented by the following general formula (3).

In formula (3),
X and Ar ⁴ are each independently hydrogen, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted diarylamino, optionally substituted diheteroarylamino, optionally substituted arylheteroarylamino, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkoxy, optionally substituted Aryloxy, optionally substituted arylthio or optionally substituted silyl, all X and Ar ⁴ cannot be hydrogen at the same time,
At least one hydrogen in the compound represented by formula (3) may be substituted with halogen, cyano, deuterium, or optionally substituted heteroaryl.

Further, a multimer (preferably a dimer) may be formed using the structure represented by formula (3) as a unit structure. In this case, examples include a form in which the unit structures represented by formula (3) are bonded to each other via Groups having a divalent bond such as a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, and a phenyl-substituted carbazole ring can be mentioned.

Details of the above aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or silyl are explained in the section of preferred embodiments below. Substituents for these groups include aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy, aryloxy, arylthio or silyl, These details are also explained in the section of preferred embodiments below.

Preferred embodiments of the above anthracene compound will be explained below. The definitions of the symbols in the structure below are the same as the definitions above.

In general formula (3), X is each independently a group represented by the above formula (3-X1), formula (3-X2) or formula (3-X3), and , the group represented by formula (3-X2) or formula (3-X3) is bonded to the anthracene ring of formula (3) at *. Preferably, two Xs do not simultaneously become groups represented by formula (3-X3). More preferably, two Xs do not simultaneously become groups represented by formula (3-X2).

Further, a multimer (preferably a dimer) may be formed using the structure represented by formula (3) as a unit structure. In this case, examples include a form in which the unit structures represented by formula (3) are bonded to each other via Groups having a divalent bond such as a dibenzofuran ring, a dibenzothiophene ring, a carbazole ring, a benzocarbazole ring, and a phenyl-substituted carbazole ring can be mentioned.

The naphthylene moiety in formula (3-X1) and formula (3-X2) may be fused with one benzene ring. The structure condensed in this way is as follows.

Ar ¹ and Ar ² are each independently hydrogen, phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or in the above formula (A) The represented groups (including carbazolyl groups, benzocarbazolyl groups, and phenyl-substituted carbazolyl groups). In addition, when Ar ¹ or Ar ² is a group represented by formula (A), the group represented by formula (A) is a group represented by formula (3-X1) or formula (3-X2) in its *. Combines with naphthalene ring.

Ar ³ is phenyl, biphenylyl, terphenylyl, quaterphenylyl, naphthyl, phenanthryl, fluorenyl, benzofluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by the above formula (A) (carbazolyl group, benzocarba (also includes zolyl groups and phenyl-substituted carbazolyl groups). In addition, when Ar ³ is a group represented by formula (A), the group represented by formula (A) is bonded to the single bond represented by the straight line in formula (3-X3) at its *. . That is, the anthracene ring of formula (3) and the group represented by formula (A) are directly bonded.

Further, Ar ³ may have a substituent, and at least one hydrogen in Ar ³ may further include alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, phenyl, biphenylyl, terphenylyl, naphthyl, phenanthryl. , fluorenyl, chrysenyl, triphenylenyl, pyrenyl, or a group represented by the above formula (A) (including a carbazolyl group and a phenyl-substituted carbazolyl group). Note that when the substituent that Ar ³ has is a group represented by formula (A), the group represented by formula (A) is bonded to Ar ³ in formula (3-X3) at its *.

Ar ⁴ is each independently substituted with hydrogen, phenyl, biphenylyl, terphenylyl, naphthyl, or alkyl having 1 to 4 carbon atoms (methyl, ethyl, t-butyl, etc.) and/or cycloalkyl having 5 to 10 carbon atoms This is Cyril.

Examples of alkyl having 1 to 4 carbon atoms substituted for silyl include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, cyclobutyl, etc., and the three hydrogens in silyl are each independently , substituted with these alkyls.

Specific examples of "silyl substituted with alkyl having 1 to 4 carbon atoms" include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, trisec-butylsilyl, trit-butylsilyl, ethyl Dimethylsilyl, propyldimethylsilyl, i-propyldimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyl Diethylsilyl, t-butyldiethylsilyl, methyldipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, Examples include butyldi-i-propylsilyl, sec-butyldi-i-propylsilyl, t-butyldi-i-propylsilyl, and the like.

Cycloalkyl having 5 to 10 carbon atoms substituted with silyl includes cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, norbornenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, Bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, decahydronaphthalenyl, decahydro Examples include azulenyl, in which three hydrogens in silyl are each independently substituted with these cycloalkyl groups.

Specific examples of "silyl substituted with cycloalkyl having 5 to 10 carbon atoms" include tricyclopentylsilyl, tricyclohexylsilyl, and the like.

Substituted silyl also includes dialkylcycloalkylsilyl substituted with two alkyls and one cycloalkyl, and alkyldicycloalkylsilyl substituted with one alkyl and two cycloalkyls. Specific examples include the groups mentioned above.

Furthermore, hydrogen in the chemical structure of the anthracene compound represented by general formula (3) may be substituted with a group represented by formula (A) above. When substituted with a group represented by formula (A), the group represented by formula (A) replaces at least one hydrogen in the compound represented by formula (3) in its *.

The group represented by formula (A) is one of the substituents that the anthracene compound represented by formula (3) may have.

In the above formula (A), Y is -O-, -S- or >N-R ²⁹ , and R ²¹ to R ²⁸ are each independently hydrogen, optionally substituted alkyl, or optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted arylthio, trialkylsilyl, Tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, optionally substituted amino, halogen, hydroxy, or cyano, and adjacent groups among R ²¹ to R ²⁸ are bonded to each other to form a hydrocarbon ring. , may form an aryl ring or a heteroaryl ring, and R ²⁹ is hydrogen or an optionally substituted aryl.

The "alkyl" in "optionally substituted alkyl" in R ²¹ to R ²⁸ may be either straight chain or branched, for example, straight chain alkyl having 1 to 24 carbon atoms or straight chain alkyl having 3 to 24 carbon atoms. Branched chain alkyl is mentioned. Alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms) is preferable, alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms) is more preferable, and alkyl having 1 to 6 carbon atoms is preferable. (branched alkyl having 3 to 6 carbon atoms) is more preferred, and alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms) is particularly preferred.

Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1-Methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n- Examples include undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, and the like.

The "cycloalkyl" of "optionally substituted cycloalkyl" in R ²¹ to R ²⁸ includes cycloalkyl having 3 to 24 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, and cycloalkyl having 3 to 16 carbon atoms. , cycloalkyl having 3 to 14 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, cycloalkyl having 5 to 8 carbon atoms, cycloalkyl having 5 to 6 carbon atoms, cycloalkyl having 5 carbon atoms, and the like.

Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and alkyl (especially methyl) substituted products of these having 1 to 4 carbon atoms, norbornenyl, bicyclo [1.1.0]butyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.0]pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo [2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, diamantyl, decahydronaphthalenyl, decahydroazulenyl and the like.

Examples of "aryl" in "optionally substituted aryl" in R ²¹ to R ²⁸ include aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 16 carbon atoms, and aryl having 6 to 12 carbon atoms. aryl having 6 to 10 carbon atoms is more preferred, and aryl having 6 to 10 carbon atoms is particularly preferred.

Specific examples of "aryl" include phenyl, which is a monocyclic system, biphenylyl, which is a bicyclic system, naphthyl, which is a fused bicyclic system, and terphenylyl, which is a tricyclic system (m-terphenylyl, o-terphenylyl, p-terphenylyl). , fused tricyclic ring systems such as acenaphthylenyl, fluorenyl, phenalenyl, and phenanthrenyl; fused tetracyclic ring systems such as triphenylenyl, pyrenyl, and naphthacenyl; and fused pentacyclic ring systems such as perylenyl and pentacenyl.

Examples of the "heteroaryl" of "optionally substituted heteroaryl" in R ²¹ to R ²⁸ include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, and Heteroaryl having 2 to 20 carbon atoms is more preferred, heteroaryl having 2 to 15 carbon atoms is even more preferred, and heteroaryl having 2 to 10 carbon atoms is particularly preferred. Examples of the heteroaryl include, for example, a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

Specific examples of "heteroaryl" include pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H- indazolyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, naphthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxatiinyl, phenoxazinyl, phenothiazinyl, Phenazinyl, phenazasilinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, benzo Examples thereof include a monovalent group of a phosphole oxide ring, a monovalent group of a dibenzophosphole oxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzindolocarbazolyl, and benzobenzoindolocarbazolyl.

Examples of the "alkoxy" in "optionally substituted alkoxy" in R ²¹ to R ²⁸ include straight chain alkoxy having 1 to 24 carbon atoms or branched chain alkoxy having 3 to 24 carbon atoms. Alkoxy having 1 to 18 carbon atoms (branched alkoxy having 3 to 18 carbon atoms) is preferable, alkoxy having 1 to 12 carbon atoms (branched alkoxy having 3 to 12 carbon atoms) is more preferable, and alkoxy having 1 to 6 carbon atoms is preferable. Alkoxy (branched alkoxy having 3 to 6 carbon atoms) is more preferred, and alkoxy having 1 to 4 carbon atoms (branched alkoxy having 3 to 4 carbon atoms) is particularly preferred.

Specific examples of "alkoxy" include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy, t-butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, and the like.

The "aryloxy" in the "optionally substituted aryloxy" in R ²¹ to R ²⁸ is a group in which the hydrogen of the -OH group is substituted with an aryl, and this aryl is the one in R ²¹ to R ²⁸ described above. Reference may be made to groups described as "aryl".

The "arylthio" in "optionally substituted arylthio" in R ²¹ to R ²⁸ is a group in which the hydrogen of the -SH group is substituted with aryl, and this aryl is the "arylthio" in "optionally substituted arylthio" in R ²¹ to R ²⁸ described above ” can be cited.

Examples of "trialkylsilyl" in R ²¹ to R ²⁸ include groups in which three hydrogens in a silyl group are each independently substituted with alkyl, and this alkyl is the same as the "alkyl" in R ²¹ to R ²⁸ described above. The groups described may be cited. Preferred alkyls for substitution are those having 1 to 4 carbon atoms, and specific examples include methyl, ethyl, propyl, i-propyl, butyl, sec-butyl, t-butyl, and cyclobutyl.

Specific examples of "trialkylsilyl" include trimethylsilyl, triethylsilyl, tripropylsilyl, tri-i-propylsilyl, tributylsilyl, tri-sec-butylsilyl, tri-t-butylsilyl, ethyldimethylsilyl, propyldimethylsilyl, and i-propyl. Dimethylsilyl, butyldimethylsilyl, sec-butyldimethylsilyl, t-butyldimethylsilyl, methyldiethylsilyl, propyldiethylsilyl, i-propyldiethylsilyl, butyldiethylsilyl, sec-butyldiethylsilyl, t-butyldiethylsilyl, methyl Dipropylsilyl, ethyldipropylsilyl, butyldipropylsilyl, sec-butyldipropylsilyl, t-butyldipropylsilyl, methyldi-i-propylsilyl, ethyldi-i-propylsilyl, butyldi-i-propylsilyl, sec-butyldi-i -propylsilyl, t-butyldi-i-propylsilyl, and the like.

The "tricycloalkylsilyl" in R ²¹ to R ²⁸ includes a group in which three hydrogens in a silyl group are each independently substituted with cycloalkyl, and this cycloalkyl is the "tricycloalkylsilyl" in R ²¹ to R ²⁸ described above. Reference may be made to the groups explained as "cycloalkyl". Preferred cycloalkyl for substitution is cycloalkyl having 5 to 10 carbon atoms, specifically cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclo[1.1.1]pentyl, bicyclo[ 2.1.0] pentyl, bicyclo[2.1.1]hexyl, bicyclo[3.1.0]hexyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, adamantyl, Examples include decahydronaphthalenyl and decahydroazulenyl.

Specific examples of "tricycloalkylsilyl" include tricyclopentylsilyl, tricyclohexylsilyl, and the like.

Specific examples of dialkylcycloalkylsilyl substituted with two alkyl and one cycloalkyl and alkyldicycloalkylsilyl substituted with one alkyl and two cycloalkyl are selected from the above-mentioned specific alkyl and cycloalkyl. Examples include silyl substituted with a group.

Examples of the "substituted amino" of the "optionally substituted amino" in R ²¹ to R ²⁸ include an amino group in which two hydrogen atoms are substituted with aryl or heteroaryl. An amino in which two hydrogens are substituted with aryl is diaryl-substituted amino, an amino in which two hydrogens are substituted with heteroaryl is diheteroaryl-substituted amino, and an amino in which two hydrogens are substituted with aryl and heteroaryl. is an arylheteroaryl substituted amino. As the aryl and heteroaryl, the groups explained as "aryl" and "heteroaryl" in R ²¹ to R ²⁸ above can be cited.

Specific examples of "substituted amino" include diphenylamino, dinaphthylamino, phenylnaphthylamino, dipyridylamino, phenylpyridylamino, naphthylpyridylamino, and the like.

Examples of the "halogen" for R ²¹ to R ²⁸ include fluorine, chlorine, bromine, and iodine.

Some of the groups described as R ²¹ to R ²⁸ may be substituted as described above, in which case the substituents include alkyl, cycloalkyl, aryl or heteroaryl. As the alkyl, cycloalkyl, aryl or heteroaryl, the groups explained as "alkyl", "cycloalkyl", "aryl" or "heteroaryl" in R ²¹ to R ²⁸ above can be cited.

R ²⁹ in “>NR ²⁹ ” as Y is hydrogen or an optionally substituted aryl, and as this aryl, the groups explained as “aryl” in R ²¹ to R ²⁸ above can be cited. As the substituent, the groups explained as substituents for R ²¹ to R ²⁸ can be cited.

Adjacent groups among R ²¹ to R ²⁸ may be bonded to each other to form a hydrocarbon ring, an aryl ring, or a heteroaryl ring. When it does not form a ring, it is a group represented by the following formula (A-1), and when it forms a ring, it is represented by any of the following formulas (A-2) to (A-14), for example. Examples include groups. Note that at least one hydrogen in the group represented by any of formulas (A-1) to (A-14) is alkyl, cycloalkyl, aryl, heteroaryl, alkoxy, aryloxy, arylthio, trialkylsilyl. , tricycloalkylsilyl, dialkylcycloalkylsilyl, alkyldicycloalkylsilyl, diaryl-substituted amino, diheteroaryl-substituted amino, arylheteroaryl-substituted amino, halogen, hydroxy or cyano. * in each structural formula represents a bonding position, and Y has the same definition as above.

Examples of the ring formed by bonding adjacent groups to each other include a cyclohexane ring in the case of a hydrocarbon ring, and examples of the aryl ring and heteroaryl ring include the "aryl" and "heteroaryl" in R ²¹ to R ²⁸ described above. These rings are formed so as to be fused with one or two benzene rings in the above formula (A-1).

Examples of the group represented by formula (A) include groups represented by any of the above formulas (A-1) to (A-14); -5) and groups represented by any of formulas (A-12) to (A-14) are preferred, and groups represented by any of formulas (A-1) to (A-4) above are preferred. is more preferable, a group represented by any one of the above formula (A-1), formula (A-3) and formula (A-4) is even more preferable, and a group represented by the above formula (A-1) is more preferably Particularly preferred.

The group represented by formula (A) is a naphthalene ring in formula (3-X1) or formula (3-X2), a single bond in formula (3-X3), or a group represented by * in formula (A). As mentioned above, it bonds with Ar ³ in (3-X3) and replaces at least one hydrogen in the compound represented by formula (3), but among these bonding forms, formula (3-X1) Alternatively, a form in which it is bonded to at least one of the naphthalene ring in formula (3-X2), the single bond in formula (3-X3), and Ar ³ in formula (3-X3) is preferable.

In addition, in the structure of the group represented by formula (A), a naphthalene ring in formula (3-X1) or formula (3-X2), a single bond in formula (3-X3), a single bond in formula (3-X3), ) in the structure of the group represented by formula (A), and the position substituted with at least one hydrogen in the compound represented by formula ( ³ ) is For example, either of the two benzene rings in the structure of formula (A) or an adjacent group among R ²¹ to R ²⁸ in the structure of formula (A) may be located at any position in the structure of formula (A). They can be bonded at any ring formed by bonding with each other or at any position in R ²⁹ in ">NR ²⁹ " as Y in the structure of formula (A).

Examples of the group represented by formula (A) include the following groups. Y and * in the formula have the same definitions as above.

Furthermore, all or part of hydrogen in the chemical structure of the anthracene compound represented by general formula (3) may be deuterium.

Specific examples of anthracene compounds include compounds represented by any of the following formulas (3-1) to (3-142). In the structural formula below, "Me" represents a methyl group, "D" represents deuterium, and "tBu" represents a t-butyl group.

The anthracene compound represented by formula (3) includes a compound having a reactive group at a desired position of the anthracene skeleton, and a compound having a reactive group in a partial structure such as X, Ar ⁴ and the structure of formula (A). can be produced by applying Suzuki coupling, Negishi coupling, and other known coupling reactions using as a starting material. Examples of the reactive group of these reactive compounds include halogen and boronic acid. As a specific manufacturing method, for example, the synthesis method in paragraphs [0089] to [0175] of International Publication No. 2014/141725 can be referred to.

<Fluorene compounds>
The compound represented by general formula (4) basically functions as a host.

In the above formula (4),
R ¹ to R ¹⁰ are each independently hydrogen, aryl, heteroaryl (the heteroaryl may be bonded to the fluorene skeleton in the above formula (4) via a linking group), diarylamino, dihetero arylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, and at least one hydrogen in R ¹ to R ¹⁰ may be substituted with aryl, heteroaryl, alkyl or cycloalkyl. ,
Furthermore, R ¹ and R ² , R ² and R ³ , R ³ and R ⁴ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , R ⁷ and R ⁸ or R ⁹ and R ¹⁰ are each independently bonded. may form a condensed ring or a spiro ring, and at least one hydrogen in the formed ring may be an aryl or a heteroaryl (the heteroaryl may be bonded to the formed ring via a linking group). ), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, and at least one hydrogen in these substituents is aryl, heteroaryl, alkyl or may be substituted with cycloalkyl, and
At least one hydrogen in the compound represented by formula (4) may be substituted with halogen, cyano, or deuterium.

For details of each group in the definition of the above formula (4), the explanation regarding the polycyclic aromatic compound represented by the above formula (1) or formula (2) can be cited.

Examples of the alkenyl in R ¹ to R ¹⁰ include alkenyl having 2 to 30 carbon atoms, preferably alkenyl having 2 to 20 carbon atoms, more preferably alkenyl having 2 to 10 carbon atoms, and alkenyl having 2 to 6 carbon atoms. Alkenyl is more preferred, and alkenyl having 2 to 4 carbon atoms is particularly preferred. Preferred alkenyls are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

式（４－Ａｒ１）から式（４－Ａｒ５）中、Ｙ^１は、それぞれ独立して、Ｏ、ＳまたはＮ－Ｒであり、Ｒはフェニル、ビフェニリル、ナフチル、アントラセニルまたは水素であり、
上記式（４－Ａｒ１）から式（４－Ａｒ５）の構造における少なくとも１つの水素はフェニル、ビフェニリル、ナフチル、アントラセニル、フェナントレニル、メチル、エチル、プロピル、または、ブチルで置換されていてもよい。 In addition, as a specific example of heteroaryl, any one from the following formula (4-Ar1), formula (4-Ar2), formula (4-Ar3), formula (4-Ar4) or formula (4-Ar5) Also included are monovalent groups represented by excluding one hydrogen atom.

In formulas (4-Ar1) to (4-Ar5), Y ¹ is each independently O, S or NR, R is phenyl, biphenylyl, naphthyl, anthracenyl or hydrogen,
At least one hydrogen in the structures of formulas (4-Ar1) to (4-Ar5) above may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl.

These heteroaryls may be bonded to the fluorene skeleton in formula (4) above via a linking group. That is, the fluorene skeleton in formula (4) and the above-mentioned heteroaryl may not only be directly bonded, but also be bonded through a linking group between them. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH ₂ CH ₂ -, -CH ₂ CH ₂ O-, or -OCH ₂ CH ₂ O-.

Furthermore, R ¹ and R ² , R ² and R ³ , R ³ and R ⁴ , R ⁵ and R ⁶ , R ⁶ and R ⁷ , or R ⁷ and R ⁸ in formula (4) are each independently bonded. R ⁹ and R ¹⁰ may combine to form a spiro ring. The condensed ring formed by R ¹ to R ⁸ is a ring condensed to the benzene ring in formula (4), and is an aliphatic ring or an aromatic ring. Preferably, it is an aromatic ring, and examples of the structure including a benzene ring in formula (4) include a naphthalene ring and a phenanthrene ring. The spiro ring formed by R ⁹ and R ¹⁰ is a ring spiro-bonded to the 5-membered ring in formula (4), and is an aliphatic ring or an aromatic ring. Preferably it is an aromatic ring, such as a fluorene ring.

The compound represented by the general formula (4) is preferably a compound represented by the following formula (4-1), formula (4-2) or formula (4-3), and each of the compounds represented by the general formula (4-1), ), a compound in which the benzene ring formed by combining R ¹ and R ² is fused, a compound in which the benzene ring formed by combining R ³ and R ⁴ in general formula (4) is fused, a compound in which the benzene ring formed by combining R 3 and R 4 in general formula (4) is fused, ) in which none of R ¹ to R ⁸ are bonded.

The definitions of R ¹ to R 10 in formula (4-1), formula (4-2), and formula ( ^4-3 ) are the same as the corresponding R ¹ to R ¹⁰ in formula (4), and The definitions of R ¹¹ to R ¹⁴ in 1) and formula (4-2) are also the same as R ¹ to R ¹⁰ in formula (4).

The compound represented by the general formula (4) is more preferably a compound represented by the following formula (4-1A), formula (4-2A) or formula (4-3A), each of which is represented by the formula (4-1A), formula (4-2A) or formula (4-3A), respectively. -1), a compound in which R ⁹ and R ¹⁰ are combined to form a spiro-fluorene ring in formula (4-1) or formula (4-3).

The definitions of R ² to R ⁷ in formula (4-1A), formula (4-2A) and formula (4-3A) are as follows in formula (4-1), formula (4-2) and formula (4-3). The definitions of R 11 to R 14 in formula (4-1A) and formula (4-2A) are the same as the corresponding R ² to R ⁷ , and the definitions of R ¹¹ to R ¹⁴ in formula (4-1) and formula (4-2) are also the same as R ¹¹ in formula (4-1) and formula (4-2). to R is the same as ¹⁴ .

Furthermore, all or part of hydrogen in the compound represented by formula (4) may be substituted with halogen, cyano, or deuterium.

Specific examples of fluorene compounds include compounds represented by any of the following formulas (4-4) to (4-22). In addition, "Me" in the following structural formula represents a methyl group.

<Dibenzochrysene compounds>
The dibenzochrysene compound as a host is, for example, a compound represented by the following general formula (5).

In the above formula (5),
R ¹ to R ¹⁶ each independently represent hydrogen, aryl, heteroaryl (the heteroaryl may be bonded to the dibenzochrysene skeleton in the above formula (5) via a linking group), diarylamino, diaryl, heteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, even if at least one hydrogen in R ¹ to R ¹⁶ is substituted with aryl, heteroaryl, alkyl or cycloalkyl. often,
Further, adjacent groups among R ¹ to R ¹⁶ may be bonded to each other to form a condensed ring, and at least one hydrogen in the formed ring is an aryl or a heteroaryl (the heteroaryl is connected via a linking group). may be bonded to the formed ring), diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, cycloalkyl, alkenyl, alkoxy or aryloxy, and these substitutions At least one hydrogen in the group may be substituted with aryl, heteroaryl, alkyl or cycloalkyl, and
At least one hydrogen in the compound represented by formula (5) may be substituted with halogen, cyano, or deuterium.

For details of each group in the definition of formula (5) above, the explanation regarding the polycyclic aromatic compound represented by formula (1) or formula (2) described above can be cited.

Examples of alkenyl in the definition of formula (5) above include alkenyl having 2 to 30 carbon atoms, preferably alkenyl having 2 to 20 carbon atoms, more preferably alkenyl having 2 to 10 carbon atoms, and alkenyl having 2 to 30 carbon atoms. Alkenyl having 6 carbon atoms is more preferred, and alkenyl having 2 to 4 carbon atoms is particularly preferred. Preferred alkenyls are vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, or 5-hexenyl.

式（５－Ａｒ１）から式（５－Ａｒ５）中、Ｙ^１は、それぞれ独立して、Ｏ、ＳまたはＮ－Ｒであり、Ｒはフェニル、ビフェニリル、ナフチル、アントラセニルまたは水素であり、
上記式（５－Ａｒ１）から式（５－Ａｒ５）の構造における少なくとも１つの水素はフェニル、ビフェニリル、ナフチル、アントラセニル、フェナントレニル、メチル、エチル、プロピル、または、ブチルで置換されていてもよい。 Specific examples of heteroaryl include any one of the compounds of the following formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4), or formula (5-Ar5). Also included are monovalent groups represented by excluding one hydrogen atom.

In formulas (5-Ar1) to (5-Ar5), Y ¹ is each independently O, S or NR, R is phenyl, biphenylyl, naphthyl, anthracenyl or hydrogen,
At least one hydrogen in the structures of formulas (5-Ar1) to (5-Ar5) above may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl, methyl, ethyl, propyl, or butyl.

These heteroaryls may be bonded to the dibenzochrysene skeleton in formula (5) above via a linking group. That is, the dibenzochrysene skeleton in formula (5) and the above-mentioned heteroaryl may not only be directly bonded, but also may be bonded through a linking group between them. Examples of the linking group include phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH ₂ CH ₂ -, -CH ₂ CH ₂ O-, or -OCH ₂ CH ₂ O-.

In the compound represented by general formula (5), R ¹ , R ⁴ , R ⁵ , R ⁸ , R ⁹ , R ¹² , R ¹³ and R ¹⁶ are preferably hydrogen. In this case, R ² , R ³ , R ⁶ , R ⁷ , R ¹⁰ , R ¹¹ , R ¹⁴ and R ¹⁵ in formula (5) are each independently hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, phenanthrenyl. , a monovalent group having the structure of the above formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), formula (5-Ar4) or formula (5-Ar5) (1 having the structure The valent group is phenylene, biphenylene, naphthylene, anthracenylene, methylene, ethylene, -OCH ₂ CH ₂ -, -CH ₂ CH ₂ O-, or -OCH ₂ CH ₂ O- via the above formula (5). ), methyl, ethyl, propyl, or butyl is preferable.

The compound represented by general formula (5) is more preferably R ¹ , R ² , R ⁴ , R ⁵ , R ⁷ , R 8 , R ⁹ , R ¹⁰ , R ¹² , R ¹³ , R ¹⁵ and ^{R 16} is hydrogen. In this case, at least one (preferably one or two, more preferably one) of R ³ , R ⁶ , R ¹¹ and R ¹⁴ in formula (5) is a single bond, phenylene, biphenylene, naphthylene, Anthracenylene, methylene, ethylene, -OCH ₂ CH ₂ -, -CH ₂ CH ₂ O-, or -OCH ₂ CH ₂ O-, the above formula (5-Ar1), formula (5-Ar2), formula (5-Ar3), a monovalent group having the structure of formula (5-Ar4) or formula (5-Ar5),
The positions other than at least one of the above (that is, positions other than those substituted by the monovalent group having the above structure) are hydrogen, phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl, and at least one of these groups One hydrogen may be substituted with phenyl, biphenylyl, naphthyl, anthracenyl, methyl, ethyl, propyl, or butyl.

Furthermore, R ² , R ³ , R ⁶ , R ⁷ , R ¹⁰ , R ¹¹ , R ¹⁴ and R ¹⁵ in formula (5) are represented by the above formulas (5-Ar1) to (5-Ar5). When a monovalent group having a structure is selected, at least one hydrogen in the structure may bond with any of R ¹ to R ¹⁶ in formula (5) to form a single bond. .

Specific examples of dibenzochrysene compounds include compounds represented by any of the following formulas (5-1) to (5-39). Note that "tBu" in the following structural formula represents a t-butyl group.

The above-mentioned materials for the light-emitting layer (host material and dopant material) are polymeric compounds obtained by polymerizing reactive compounds substituted with reactive substituents as monomers, or crosslinked polymers thereof, or main chains thereof. A pendant type polymer compound obtained by reacting a type polymer with the above-mentioned reactive compound, or a pendant type polymer crosslinked product thereof can also be used as a material for a light emitting layer. As for the reactive substituent in this case, the explanation for the polycyclic aromatic compound represented by formula (1) or formula (2) can be cited.
Details of the uses of such polymer compounds and crosslinked polymers will be described later.

<Example of polymer host material>

In formula (SPH-1),
MU is a divalent group each independently represented by removing any two hydrogen atoms from an aromatic compound, and EC is each independently represented by removing any one hydrogen atom from an aromatic compound. It is a valent group, two hydrogens in MU are replaced with EC or MU, and k is an integer from 2 to 50,000.

More specifically,
MU is each independently arylene, heteroarylene, diarylenearylamino, diarylenearylboryl, oxaboline-diyl, azaboline-diyl,
EC is each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino or aryloxy;
At least one hydrogen in MU and EC may be further substituted with aryl, heteroaryl, diarylamino, alkyl and cycloalkyl,
k is an integer from 2 to 50,000.
k is preferably an integer from 20 to 50,000, more preferably from 100 to 50,000.

At least one hydrogen in MU and EC in formula (SPH-1) may be substituted with alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 24 carbon atoms, halogen, or deuterium, and further, Any -CH ₂ - in the alkyl may be substituted with -O- or -Si(CH ₃ ) ₂ -, and the -CH ₂ - directly connected to EC in the formula (SPH-1) in the alkyl Any -CH ₂ - except for may be substituted with arylene having 6 to 24 carbon atoms, and any hydrogen in the alkyl may be substituted with fluorine.

Examples of MU include a divalent group represented by removing any two hydrogen atoms from any of the following compounds.

More specifically, divalent groups represented by any of the following structures may be mentioned. In these, MUs combine with other MUs or ECs at *.

Furthermore, examples of EC include monovalent groups represented by any of the following structures. In these, EC joins MU at *.

In the compound represented by formula (SPH-1), from the viewpoint of solubility and coating film formation properties, 10 to 100% of the total number of MUs (k) in the molecule has an alkyl group having 1 to 24 carbon atoms. is preferable, and it is more preferable that 30 to 100% of the total number of MU in the molecule (k) has alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms); It is further preferred that 50 to 100% of MU in k) has alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). On the other hand, from the viewpoint of in-plane orientation and charge transport, it is preferable that 10 to 100% of the total number of MUs (k) in the molecule have alkyl atoms having 7 to 24 carbon atoms; It is more preferable that 30 to 100% of MU of ) has an alkyl having 7 to 24 carbon atoms (branched alkyl having 7 to 24 carbon atoms).

Details of the uses of such polymer compounds and crosslinked polymers will be described later.

<Electron injection layer and electron transport layer in organic electroluminescent device>
The electron injection layer 107 plays a role of efficiently injecting electrons moving from the cathode 108 into the light emitting layer 105 or the electron transport layer 106. The electron transport layer 106 plays a role of efficiently transporting electrons injected from the cathode 108 or electrons injected from the cathode 108 via the electron injection layer 107 to the light emitting layer 105. The electron transport layer 106 and the electron injection layer 107 are each formed by laminating and mixing one or more electron transport/injection materials, or by a mixture of an electron transport/injection material and a polymer binder.

The electron injection/transport layer is a layer that is in charge of injecting electrons from the cathode and further transporting electrons, and it is desirable that the electron injection efficiency is high and that the injected electrons are efficiently transported. For this purpose, it is preferable that the material has high electron affinity, high electron mobility, excellent stability, and does not easily generate trapping impurities during production and use. However, when considering the transport balance of holes and electrons, if the role is to efficiently prevent holes from the anode from flowing to the cathode side without recombining, the electron transport capacity is not so great. Even if it is not high, it has the same effect of improving luminous efficiency as a material with high electron transport ability. Therefore, the electron injection/transport layer in this embodiment may also include the function of a layer that can efficiently block the movement of holes.

As the material (electron transport material) forming the electron transport layer 106 or the electron injection layer 107, a polycyclic aromatic compound represented by the above general formula (1) or general formula (2) can be used. In addition, any compounds that have been conventionally used as electron transfer compounds in photoconductive materials and known compounds used in electron injection layers and electron transport layers of organic EL devices can be arbitrarily selected and used.

Materials used for the electron transport layer or electron injection layer include compounds consisting of an aromatic ring or a heteroaromatic ring composed of one or more atoms selected from carbon, hydrogen, oxygen, sulfur, silicon, and phosphorus; It is preferable to contain at least one selected from pyrrole derivatives, fused ring derivatives thereof, and metal complexes having electron-accepting nitrogen. Specifically, fused ring aromatic ring derivatives such as naphthalene and anthracene, styryl aromatic ring derivatives represented by 4,4'-bis(diphenylethenyl)biphenyl, perinone derivatives, coumarin derivatives, and naphthalimide derivatives. , quinone derivatives such as anthraquinone and diphenoquinone, phosphine oxide derivatives, carbazole derivatives, and indole derivatives. Examples of metal complexes having electron-accepting nitrogen include hydroxyazole complexes such as hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. These materials can be used alone or in combination with different materials.

Specific examples of other electron transfer compounds include pyridine derivatives, naphthalene derivatives, anthracene derivatives, phenanthroline derivatives, perinone derivatives, coumarin derivatives, naphthalimide derivatives, anthraquinone derivatives, diphenoquinone derivatives, diphenylquinone derivatives, perylene derivatives, and oxadiazoles. derivatives (1,3-bis[(4-t-butylphenyl)1,3,4-oxadiazolyl]phenylene, etc.), thiophene derivatives, triazole derivatives (N-naphthyl-2,5-diphenyl-1,3,4- triazole, etc.), thiadiazole derivatives, metal complexes of oxine derivatives, quinolinol metal complexes, quinoxaline derivatives, polymers of quinoxaline derivatives, benzazole compounds, gallium complexes, pyrazole derivatives, perfluorinated phenylene derivatives, triazine derivatives, pyrazine derivatives, benzoquinolines derivatives (2,2'-bis(benzo[h]quinolin-2-yl)-9,9'-spirobifluorene, etc.), imidazopyridine derivatives, borane derivatives, benzimidazole derivatives (tris(N-phenylbenzimidazole- (2-yl)benzene, etc.), benzoxazole derivatives, benzothiazole derivatives, quinoline derivatives, oligopyridine derivatives such as terpyridine, bipyridine derivatives, terpyridine derivatives (1,3-bis(2,2':6,2''-terpyridine) (4'-yl)benzene, benzene, etc.), naphthyridine derivatives (bis(1-naphthyl)-4-(1,8-naphthyridin-2-yl)phenylphosphine oxide, etc.), aldazine derivatives, carbazole derivatives, indole derivatives, phosphine oxide derivatives, bisstyryl derivatives, etc.

Further, metal complexes having electron-accepting nitrogen can also be used, such as hydroxyazole complexes such as quinolinol metal complexes and hydroxyphenyloxazole complexes, azomethine complexes, tropolone metal complexes, flavonol metal complexes, and benzoquinoline metal complexes. Can be mentioned.

The above-mentioned materials can be used alone, but they can also be used in combination with different materials.

Among the materials mentioned above, borane derivatives, pyridine derivatives, fluoranthene derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinolinol metals. Complexes are preferred.

上記式（ＥＴＭ－１）中、Ｒ^１１およびＲ^１２は、それぞれ独立して、水素、アルキル、シクロアルキル、置換されていてもよいアリール、置換されているシリル、置換されていてもよい窒素含有複素環、またはシアノの少なくとも１つであり、Ｒ^１３～Ｒ^１６は、それぞれ独立して、置換されていてもよいアルキル、置換されていてもよいシクロアルキルまたは置換されていてもよいアリールであり、Ｘは、置換されていてもよいアリーレンであり、Ｙは、置換されていてもよい炭素数１６以下のアリール、置換されているボリル、または置換されていてもよいカルバゾリルであり、そして、ｎはそれぞれ独立して０～３の整数である。また、「置換されていてもよい」または「置換されている」場合の置換基としては、アリール、ヘテロアリール、アルキルまたはシクロアルキルなどが挙げられる。 <Borane derivative>
The borane derivative is, for example, a compound represented by the following general formula (ETM-1), and is disclosed in detail in JP-A No. 2007-27587.

In the above formula (ETM-1), R ¹¹ and R ¹² are each independently hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing is at least one of a heterocycle or cyano, and R ¹³ to R ¹⁶ are each independently an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl; , X is an optionally substituted arylene, Y is an optionally substituted aryl having 16 or less carbon atoms, a substituted boryl, or an optionally substituted carbazolyl, and n are each independently an integer from 0 to 3. Further, examples of the substituent in the case of "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl.

式（ＥＴＭ－１－１）中、Ｒ^１１およびＲ^１２は、それぞれ独立して、水素、アルキル、シクロアルキル、置換されていてもよいアリール、置換されているシリル、置換されていてもよい窒素含有複素環、またはシアノの少なくとも１つであり、Ｒ^１３～Ｒ^１６は、それぞれ独立して、置換されていてもよいアルキル、置換されていてもよいシクロアルキルまたは置換されていてもよいアリールであり、Ｒ^２１およびＲ^２２は、それぞれ独立して、水素、アルキル、シクロアルキル、置換されていてもよいアリール、置換されているシリル、置換されていてもよい窒素含有複素環、またはシアノの少なくとも１つであり、Ｘ^１は、置換されていてもよい炭素数２０以下のアリーレンであり、ｎはそれぞれ独立して０～３の整数であり、そして、ｍはそれぞれ独立して０～４の整数である。また、「置換されていてもよい」または「置換されている」場合の置換基としては、アリール、ヘテロアリール、アルキルまたはシクロアルキルなどが挙げられる。

式（ＥＴＭ－１－２）中、Ｒ^１１およびＲ^１２は、それぞれ独立して、水素、アルキル、シクロアルキル、置換されていてもよいアリール、置換されているシリル、置換されていてもよい窒素含有複素環、またはシアノの少なくとも１つであり、Ｒ^１３～Ｒ^１６は、それぞれ独立して、置換されていてもよいアルキル、置換されていてもよいシクロアルキルまたは置換されていてもよいアリールであり、Ｘ^１は、置換されていてもよい炭素数２０以下のアリーレンであり、そして、ｎはそれぞれ独立して０～３の整数である。また、「置換されていてもよい」または「置換されている」場合の置換基としては、アリール、ヘテロアリール、アルキルまたはシクロアルキルなどが挙げられる。 Among the compounds represented by the above general formula (ETM-1), compounds represented by the following general formula (ETM-1-1) and compounds represented by the following general formula (ETM-1-2) are preferred.

In formula (ETM-1-1), R ¹¹ and R ¹² are each independently hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen at least one of a containing heterocycle or cyano, and R ¹³ to R ¹⁶ are each independently an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl. and R ²¹ and R ²² each independently represent at least one of hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen-containing heterocycle, or cyano. X ¹ is an optionally substituted arylene having 20 or less carbon atoms, n is each independently an integer of 0 to 3, and m is each independently an integer of 0 to 4. is an integer. Further, examples of the substituent in the case of "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl.

In formula (ETM-1-2), R ¹¹ and R ¹² are each independently hydrogen, alkyl, cycloalkyl, optionally substituted aryl, substituted silyl, optionally substituted nitrogen at least one of a containing heterocycle or cyano, and R ¹³ to R ¹⁶ are each independently an optionally substituted alkyl, an optionally substituted cycloalkyl, or an optionally substituted aryl. , X ¹ is an optionally substituted arylene having 20 or less carbon atoms, and n is each independently an integer of 0 to 3. Further, examples of the substituent in the case of "optionally substituted" or "substituted" include aryl, heteroaryl, alkyl, and cycloalkyl.

（各式中、Ｒ^ａは、それぞれ独立してアルキル基、シクロアルキル基または置換されていてもよいフェニル基である。） Specific examples of X ¹ include divalent groups represented by any of the following formulas (X-1) to (X-9). * in each structural formula represents the bonding position.

(In each formula, R ^a is each independently an alkyl group, a cycloalkyl group, or an optionally substituted phenyl group.)

Specific examples of this borane derivative include the following compounds.

This borane derivative can be produced using known raw materials and known synthesis methods.

<Pyridine derivative>
The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), preferably a compound represented by the formula (ETM-2-1) or formula (ETM-2-2).

φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is an integer of 1 to 4; be.

In the above formula (ETM-2-1), R ¹¹ to R ¹⁸ are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), and cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms). alkyl) or aryl (preferably aryl having 6 to 30 carbon atoms).

In the above formula (ETM-2-2), R ¹¹ and R ¹² are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), and cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms). alkyl) or aryl (preferably aryl having 6 to 30 carbon atoms), and R ¹¹ and R ¹² may be combined to form a ring.

In each formula, the "pyridine substituent" is one of the following formulas (Py-1) to (Py-15), and each pyridine substituent is independently an alkyl having 1 to 4 carbon atoms or a carbon It may be substituted with 5 to 10 cycloalkyl groups. Further, the pyridine substituent may be bonded to φ, anthracene ring or fluorene ring in each formula via a phenylene group or naphthylene group. * in each structural formula represents the bonding position.

The pyridine substituent is any of the above formulas (Py-1) to (Py-15), and among these, any of the following formulas (Py-21) to (Py-44) It is preferable. * in each structural formula represents the bonding position.

At least one hydrogen in each pyridine derivative may be substituted with deuterium, and among the two "pyridine substituents" in the above formulas (ETM-2-1) and (ETM-2-2), may be replaced with an aryl.

The "alkyl" in R ¹¹ to R ¹⁸ may be either a straight chain or a branched chain, and includes, for example, a straight chain alkyl having 1 to 24 carbon atoms or a branched alkyl having 3 to 24 carbon atoms. Preferred "alkyl" is alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). More preferred "alkyl" is alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). More preferred "alkyl" is alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). Particularly preferred "alkyl" is alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms).

Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl, n-octyl, t-octyl (1,1,3,3-tetramethylbutyl), 1-Methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 2,6-dimethyl-4-heptyl, 3,5,5-trimethylhexyl, n-decyl, n- Examples include undecyl, 1-methyldecyl, n-dodecyl, n-tridecyl, 1-hexylheptyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-eicosyl, and the like.
Also, for example, 1-ethyl-1-methylpropyl, 1,1-diethylpropyl, 1,1-dimethylbutyl, 1-ethyl-1-methylbutyl, 1,1,4-trimethylpentyl, 1,1,2- Trimethylpropyl, 1,1-dimethyloctyl, 1,1-dimethylpentyl, 1,1-dimethylheptyl, 1,1,5-trimethylhexyl, 1-ethyl-1-methylhexyl, 1-ethyl-1,3- Dimethylbutyl, 1,1,2,2-tetramethylpropyl, 1-butyl-1-methylpentyl, 1,1-diethylbutyl, 1-ethyl-1-methylpentyl, 1,1,3-trimethylbutyl, 1 -Propyl-1-methylpentyl, 1,1,2-trimethylpropyl, 1-ethyl-1,2,2-trimethylpropyl, 1-propyl-1-methylbutyl, 1,1-dimethylhexyl and the like can also be mentioned.

As for the alkyl having 1 to 4 carbon atoms to be substituted with the pyridine substituent, the above description of alkyl can be cited.

Examples of the "cycloalkyl" in R ¹¹ to R ¹⁸ include cycloalkyl having 3 to 12 carbon atoms. Preferred "cycloalkyl" is cycloalkyl having 3 to 10 carbon atoms. More preferred "cycloalkyl" is cycloalkyl having 3 to 8 carbon atoms. More preferred "cycloalkyl" is cycloalkyl having 3 to 6 carbon atoms.
Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

As for the cycloalkyl having 5 to 10 carbon atoms to be substituted with the pyridine substituent, the above description of cycloalkyl can be cited.

As for "aryl" in R ¹¹ to R ¹⁸ , a preferable aryl is an aryl having 6 to 30 carbon atoms, a more preferable aryl is an aryl having 6 to 18 carbon atoms, and even more preferably an aryl having 6 to 14 carbon atoms. Especially preferred is aryl having 6 to 12 carbon atoms.

Specific examples of "aryl having 6 to 30 carbon atoms" include phenyl, which is a monocyclic aryl, (1-,2-)naphthyl, which is a fused bicyclic aryl, and acenaphthylene-(, which is a fused tricyclic aryl). 1-,3-,4-,5-)yl, fluorene-(1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-,2-)yl -,3-,4-,9-)phenanthryl, fused tetracyclic aryl triphenylen-(1-,2-)yl, pyrene-(1-,2-,4-)yl, naphthacen-(1- ,2-,5-)yl, fused pentacyclic aryl perylene-(1-,2-,3-)yl, pentacen-(1-,2-,5-,6-)yl, etc. .

Preferred examples of "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, phenanthryl, chrysenyl, and triphenylenyl, more preferred examples include phenyl, 1-naphthyl, 2-naphthyl, and phenanthryl, and particularly preferred examples include phenyl, 1-naphthyl, and phenanthryl. -naphthyl or 2-naphthyl.

R ¹¹ and R ¹² in the above formula (ETM-2-2) may be combined to form a ring, and as a result, the five-membered ring of the fluorene skeleton includes cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, Cyclohexane, fluorene or indene may also be spiro-bonded.

Specific examples of this pyridine derivative include the following compounds.

This pyridine derivative can be produced using known raw materials and known synthesis methods.

<Fluoranthene derivative>
The fluoranthene derivative is, for example, a compound represented by the following general formula (ETM-3), and is disclosed in detail in International Publication No. 2010/134352.

In the above formula (ETM-3), X ¹² to X ²¹ are hydrogen, halogen, linear, branched or cyclic alkyl, linear, branched or cyclic alkoxy, substituted or unsubstituted aryl, or substituted or unsubstituted Represents a heteroaryl. Here, examples of the substituent when substituted include aryl, heteroaryl, alkyl, and cycloalkyl.

Specific examples of this fluoranthene derivative include the following compounds.

<BO derivative>
The BO derivative is, for example, a polycyclic aromatic compound represented by the following formula (ETM-4) or a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following formula (ETM-4).

R ¹ to R ¹¹ are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls are bonded via a single bond or a linking group); and at least one hydrogen in R ¹ to R ¹¹ may be substituted with aryl, heteroaryl, alkyl, or cycloalkyl.

Further, adjacent groups among R ¹ to R ¹¹ may be bonded to each other to form an aryl ring or a heteroaryl ring together with ring a, ring b, or ring c, and at least one hydrogen in the formed ring is aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, diarylboryl (two aryls may be bonded via a single bond or a linking group), alkyl, cycloalkyl, alkoxy or aryl It may be substituted with oxy, and at least one hydrogen in these substituents may be substituted with aryl, heteroaryl, alkyl or cycloalkyl.

Furthermore, at least one hydrogen in the compound or structure represented by formula (ETM-4) may be substituted with halogen or deuterium.

Regarding the substituents in formula (ETM-4), the form of ring formation, and the explanation of the multimer formed by combining multiple structures of formula (ETM-4), please refer to the explanation described in International Publication No. 2015/102118 and the above. The description of the polycyclic aromatic compound represented by formula (1) or formula (2) can be cited.

Specific examples of this BO derivative include the following compounds.

This BO derivative can be produced using known raw materials and known synthesis methods.

<Anthracene derivative>
One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-1).

Ar is each independently divalent benzene or naphthalene, and R ¹ to R ⁴ are each independently hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, or It has 6 to 20 aryls.

Ar can be appropriately selected independently from divalent benzene or naphthalene, and the two Ars may be different or the same, but from the viewpoint of ease of synthesis of the anthracene derivative, they are the same. It is preferable that Ar combines with pyridine to form a "site consisting of Ar and pyridine", and this site can be used, for example, as an anthracene group as a group represented by any of the following formulas (Py-1) to (Py-12). is combined with * in each structural formula represents the bonding position.

Among these groups, groups represented by any of the above formulas (Py-1) to (Py-9) are preferred, and groups represented by any of the above formulas (Py-1) to (Py-6) are preferred. More preferred are groups such as The two "sites consisting of Ar and pyridine" that bind to anthracene may have the same or different structures, but preferably have the same structure from the viewpoint of ease of synthesizing the anthracene derivative. However, from the viewpoint of device characteristics, it is preferable that the structures of the two "sites consisting of Ar and pyridine" be the same or different.

The alkyl having 1 to 6 carbon atoms in R ¹ to R ⁴ may be either straight chain or branched chain. That is, it is a straight chain alkyl having 1 to 6 carbon atoms or a branched alkyl having 3 to 6 carbon atoms. More preferred is alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), n-hexyl, Examples include 1-methylpentyl, 3,3-dimethylbutyl, or 2-ethylbutyl, and methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, or t-butyl are preferred, and methyl, Ethyl or t-butyl is more preferred.

Specific examples of cycloalkyl having 3 to 6 carbon atoms in R ¹ to R ⁴ include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, dimethylcyclohexyl, and the like.

The aryl having 6 to 20 carbon atoms in R ¹ to R ⁴ is preferably an aryl having 6 to 16 carbon atoms, more preferably an aryl having 6 to 12 carbon atoms, and particularly preferably an aryl having 6 to 10 carbon atoms.

Specific examples of "aryl having 6 to 20 carbon atoms" include monocyclic aryl such as phenyl, (o-,m-,p-)tolyl, (2,3-,2,4-,2,5- ,2,6-,3,4-,3,5-)xylyl, mesityl (2,4,6-trimethylphenyl), (o-,m-,p-)cumenyl, bicyclic aryl (2 -,3-,4-)biphenylyl, (1-,2-)naphthyl which is a fused bicyclic aryl, and terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4) which is a tricyclic aryl. '-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o-terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2 -yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl-2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p- terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl), fused tricyclic aryl, anthracen-(1-,2-,9-)yl, acenaphthylene- (1-,3-,4-,5-)yl, fluoren-(1-,2-,3-,4-,9-)yl, phenalen-(1-,2-)yl, (1-, 2-,3-,4-,9-)phenanthryl, fused tetracyclic aryl triphenylen-(1-,2-)yl, pyren-(1-,2-,4-)yl, tetracen-(1 -,2-,5-)yl, perylene-(1-,2-,3-)yl which is a fused pentacyclic aryl, and the like.

Preferred "aryl having 6 to 20 carbon atoms" is phenyl, biphenylyl, terphenylyl or naphthyl, more preferably phenyl, biphenylyl, 1-naphthyl, 2-naphthyl or m-terphenyl-5'-yl, More preferably phenyl, biphenylyl, 1-naphthyl or 2-naphthyl, most preferably phenyl.

One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-2).

Each Ar ¹ is independently a single bond, divalent benzene, naphthalene, anthracene, fluorene, or phenalene.

Ar ² is each independently an aryl having 6 to 20 carbon atoms, and the same explanation as "aryl having 6 to 20 carbon atoms" in the above formula (ETM-5-1) can be cited. Aryl having 6 to 16 carbon atoms is preferred, aryl having 6 to 12 carbon atoms is more preferred, and aryl having 6 to 10 carbon atoms is particularly preferred. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, and the like.

R ¹ to R ⁴ are each independently hydrogen, alkyl having 1 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, or aryl having 6 to 20 carbon atoms, and the above formula (ETM-5-1) You can cite the explanation in .

Specific examples of these anthracene derivatives include the following compounds.

These anthracene derivatives can be produced using known raw materials and known synthesis methods.

<Benzofluorene derivative>
The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6).

Ar ¹ is each independently an aryl having 6 to 20 carbon atoms, and the same explanation as "aryl having 6 to 20 carbon atoms" in the above formula (ETM-5-1) can be cited. Aryl having 6 to 16 carbon atoms is preferred, aryl having 6 to 12 carbon atoms is more preferred, and aryl having 6 to 10 carbon atoms is particularly preferred. Specific examples include phenyl, biphenylyl, naphthyl, terphenylyl, anthracenyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, and the like.

Ar ² is each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably aryl having 6 to 30 carbon atoms). ), and two Ar ² may be bonded to form a ring.

The "alkyl" in Ar ² may be either straight chain or branched, and includes, for example, straight chain alkyl having 1 to 24 carbon atoms or branched chain alkyl having 3 to 24 carbon atoms. Preferred "alkyl" is alkyl having 1 to 18 carbon atoms (branched alkyl having 3 to 18 carbon atoms). More preferred "alkyl" is alkyl having 1 to 12 carbon atoms (branched alkyl having 3 to 12 carbon atoms). More preferred "alkyl" is alkyl having 1 to 6 carbon atoms (branched alkyl having 3 to 6 carbon atoms). Particularly preferred "alkyl" is alkyl having 1 to 4 carbon atoms (branched alkyl having 3 to 4 carbon atoms). Specific examples of "alkyl" include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, isopentyl, neopentyl, t-pentyl (t-amyl), Examples include n-hexyl, 1-methylpentyl, 3,3-dimethylbutyl, 2-ethylbutyl, n-heptyl, 1-methylhexyl and the like.

Examples of the "cycloalkyl" in Ar ² include cycloalkyl having 3 to 12 carbon atoms. Preferred "cycloalkyl" is cycloalkyl having 3 to 10 carbon atoms. More preferred "cycloalkyl" is cycloalkyl having 3 to 8 carbon atoms. More preferred "cycloalkyl" is cycloalkyl having 3 to 6 carbon atoms. Specific examples of "cycloalkyl" include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl, and dimethylcyclohexyl.

As for "aryl" in Ar ² , preferable aryl is aryl having 6 to 30 carbon atoms, more preferable aryl is aryl having 6 to 18 carbon atoms, still more preferably aryl having 6 to 14 carbon atoms, and especially Aryl having 6 to 12 carbon atoms is preferred.

Specific examples of "aryl having 6 to 30 carbon atoms" include phenyl, naphthyl, acenaphthylenyl, fluorenyl, phenalenyl, phenanthryl, triphenylenyl, pyrenyl, naphthacenyl, perylenyl, and pentacenyl.

Two Ar ² may be combined to form a ring, and as a result, cyclobutane, cyclopentane, cyclopentene, cyclopentadiene, cyclohexane, fluorene, indene, etc. are spiro-bonded to the 5-membered ring of the fluorene skeleton. It's okay.

Specific examples of this benzofluorene derivative include the following compounds.

This benzofluorene derivative can be produced using known raw materials and known synthesis methods.

Ｒ^５は、置換または無置換の、炭素数１～２０のアルキル、炭素数３～２０のシクロアルキル、炭素数６～２０のアリールまたは炭素数５～２０のヘテロアリールであり、
Ｒ^６は、ＣＮ、置換または無置換の、炭素数１～２０のアルキル、炭素数３～２０のシクロアルキル、炭素数１～２０のヘテロアルキル、炭素数６～２０のアリール、炭素数５～２０のヘテロアリール、炭素数１～２０のアルコキシまたは炭素数６～２０のアリールオキシであり、
Ｒ^７およびＲ^８は、それぞれ独立して、置換または無置換の、炭素数６～２０のアリールまたは炭素数５～２０のヘテロアリールであり、
Ｒ^９は酸素または硫黄であり、
ｊは０または１であり、ｋは０または１であり、ｒは０～４の整数であり、ｑは１～３の整数である。
ここで、置換されている場合の置換基としては、アリール、ヘテロアリール、アルキルまたはシクロアルキルなどが挙げられる。 <Phosphine oxide derivative>
The phosphine oxide derivative is, for example, a compound represented by the following formula (ETM-7-1). Details are also described in International Publication No. 2013/079217.

R ⁵ is substituted or unsubstituted alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, or heteroaryl having 5 to 20 carbon atoms;
R ⁶ is CN, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, heteroalkyl having 1 to 20 carbon atoms, aryl having 6 to 20 carbon atoms, or 5 to 20 carbon atoms; 20 heteroaryl, alkoxy having 1 to 20 carbon atoms, or aryloxy having 6 to 20 carbon atoms,
R ⁷ and R ⁸ are each independently substituted or unsubstituted aryl having 6 to 20 carbon atoms or heteroaryl having 5 to 20 carbon atoms,
^R9 is oxygen or sulfur;
j is 0 or 1, k is 0 or 1, r is an integer from 0 to 4, and q is an integer from 1 to 3.
Here, examples of the substituent when substituted include aryl, heteroaryl, alkyl, and cycloalkyl.

The phosphine oxide derivative may be, for example, a compound represented by the following formula (ETM-7-2).

R ¹ to R ³ may be the same or different, and are hydrogen, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, a cycloalkenyl group, an alkynyl group, an alkoxy group, an alkylthio group, a cycloalkylthio group, an aryl ether group , an arylthioether group, an aryl group, a heterocyclic group, a halogen, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an amino group, a nitro group, a silyl group, and in the condensed ring formed between adjacent substituents. selected from.

Ar ¹ may be the same or different and is an arylene group or a heteroarylene group. Ar ² may be the same or different and are an aryl group or a heteroaryl group. However, at least one of Ar ¹ and Ar ² has a substituent, or forms a condensed ring with an adjacent substituent. n is an integer from 0 to 3; when n is 0, no unsaturated structural moiety exists; when n is 3, R ¹ does not exist.

Among these substituents, the alkyl group refers to a saturated aliphatic hydrocarbon group such as a methyl group, an ethyl group, a propyl group, a butyl group, and may be unsubstituted or substituted. There are no particular restrictions on the substituent when substituted, and examples thereof include an alkyl group, an aryl group, a heterocyclic group, and the like, and this point is also common to the following description. Further, the number of carbon atoms in the alkyl group is not particularly limited, but is usually in the range of 1 to 20 from the viewpoint of availability and cost.

Further, the cycloalkyl group refers to, for example, a saturated alicyclic hydrocarbon group such as cyclopropyl, cyclohexyl, norbornyl, and adamantyl, which may be unsubstituted or substituted. The number of carbon atoms in the alkyl group moiety is not particularly limited, but is usually in the range of 3 to 20.

Furthermore, an aralkyl group refers to an aromatic hydrocarbon group via an aliphatic hydrocarbon such as a benzyl group or a phenylethyl group, and both aliphatic hydrocarbons and aromatic hydrocarbons may be unsubstituted or substituted. It doesn't matter. The number of carbon atoms in the aliphatic moiety is not particularly limited, but is usually in the range of 1 to 20.

Further, the alkenyl group refers to an unsaturated aliphatic hydrocarbon group containing a double bond, such as a vinyl group, an allyl group, a butadienyl group, etc., and it may be unsubstituted or substituted. The number of carbon atoms in the alkenyl group is not particularly limited, but is usually in the range of 2 to 20.

Furthermore, a cycloalkenyl group refers to an unsaturated alicyclic hydrocarbon group containing a double bond, such as a cyclopentenyl group, a cyclopentadienyl group, or a cyclohexene group, and may be unsubstituted or substituted. I don't mind.

Further, the alkynyl group refers to, for example, an unsaturated aliphatic hydrocarbon group containing a triple bond such as an acetylenyl group, which may be unsubstituted or substituted. The number of carbon atoms in the alkynyl group is not particularly limited, but is usually in the range of 2 to 20.

Further, the alkoxy group refers to, for example, an aliphatic hydrocarbon group such as a methoxy group via an ether bond, and the aliphatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the alkoxy group is not particularly limited, but is usually in the range of 1 to 20.

Moreover, an alkylthio group is a group in which the oxygen atom of the ether bond of an alkoxy group is substituted with a sulfur atom.

Moreover, a cycloalkylthio group is a group in which the oxygen atom of the ether bond of a cycloalkoxy group is substituted with a sulfur atom.

Further, the aryl ether group refers to an aromatic hydrocarbon group such as a phenoxy group via an ether bond, and the aromatic hydrocarbon group may be unsubstituted or substituted. The number of carbon atoms in the aryl ether group is not particularly limited, but is usually in the range of 6 to 40.

Further, the arylthioether group is a group in which the oxygen atom of the ether bond of the aryl ether group is substituted with a sulfur atom.

Further, the aryl group refers to an aromatic hydrocarbon group such as a phenyl group, a naphthyl group, a biphenyl group, a phenanthryl group, a terphenyl group, and a pyrenyl group. The aryl group may be unsubstituted or substituted. The number of carbon atoms in the aryl group is not particularly limited, but is usually in the range of 6 to 40.

In addition, a heterocyclic group refers to a cyclic structural group having an atom other than carbon, such as a furanyl group, a thiophenyl group, an oxazolyl group, a pyridyl group, a quinolinyl group, and a carbazolyl group, which may be unsubstituted or substituted. I don't mind. The number of carbon atoms in the heterocyclic group is not particularly limited, but is usually in the range of 2 to 30.

Halogen refers to fluorine, chlorine, bromine, and iodine.

The aldehyde group, carbonyl group, and amino group can also include groups substituted with aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, heterocycles, and the like.

Furthermore, aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, and heterocycles may be unsubstituted or substituted.

The silyl group refers to a silicon compound group such as a trimethylsilyl group, which may be unsubstituted or substituted. The number of carbon atoms in the silyl group is not particularly limited, but is usually in the range of 3 to 20. Further, the silicon number is usually 1 to 6.

The condensed rings formed between adjacent substituents include, for example, Ar ¹ and R ² , Ar ¹ and R ³ , Ar 2 and R ² , Ar ² and R ³ , R ² and R ³ , Ar ^{1 and} It is a conjugated or non-conjugated condensed ring formed between Ar ² and the like. Here, when n is 1, two R ¹ may form a conjugated or non-conjugated condensed ring. These fused rings may contain nitrogen, oxygen, or sulfur atoms in the ring structure, or may be fused with another ring.

Specific examples of this phosphine oxide derivative include the following compounds.

This phosphine oxide derivative can be produced using known raw materials and known synthesis methods.

<Pyrimidine derivative>
The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), preferably a compound represented by the following formula (ETM-8-1). Details are also described in International Publication No. 2011/021689.

Each Ar is independently an optionally substituted aryl or an optionally substituted heteroaryl. n is an integer of 1 to 4, preferably an integer of 1 to 3, more preferably 2 or 3.

"Aryl" in "optionally substituted aryl" includes, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, More preferably, it is an aryl having 6 to 12 carbon atoms.

Specific examples of "aryl" include phenyl, which is a monocyclic aryl, (2-,3-,4-)biphenylyl, which is a bicyclic aryl, and (1-,2-)naphthyl, which is a fused bicyclic aryl. , tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o -terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl -2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl) , fused tricyclic aryl, acenaphthylene-(1-,3-,4-,5-)yl, fluoren-(1-,2-,3-,4-,9-)yl, phenalene-(1 -,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, tetracyclic aryl quaterphenylyl (5'-phenyl-m-terphenyl-2-yl), 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), fused tetracyclic aryl triphenylene-(1-,2 -)yl, pyrene-(1-,2-,4-)yl, naphthacen-(1-,2-,5-)yl, perylene-(1-,2-,3-) which is a fused pentacyclic aryl )yl, pentacen-(1-,2-,5-,6-)yl, and the like.

Examples of "heteroaryl" in "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, and heteroaryl having 2 to 20 carbon atoms. Aryl is more preferred, heteroaryl having 2 to 15 carbon atoms is even more preferred, and heteroaryl having 2 to 10 carbon atoms is particularly preferred. Examples of the heteroaryl include, for example, a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

Specific heteroaryls include, for example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, Benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, napthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, Phenazacylinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, benzophosphole Examples include a monovalent group of an oxide ring, a monovalent group of a dibenzophosphole oxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzindolocarbazolyl, and benzobenzoindolocarbazolyl.

Further, at least one hydrogen in the above aryl and heteroaryl may be substituted, for example, each may be substituted with the above aryl or heteroaryl.

Specific examples of this pyrimidine derivative include the following compounds.

This pyrimidine derivative can be produced using known raw materials and known synthesis methods.

<Carbazole derivative>
The carbazole derivative is, for example, a compound represented by the following formula (ETM-9), or a multimer of a plurality of compounds bonded together through a single bond or the like. Details are described in US Publication No. 2014/0197386.

Each Ar is independently an optionally substituted aryl or an optionally substituted heteroaryl. Each n is independently an integer of 0 to 4, preferably an integer of 0 to 3, more preferably 0 or 1.

"Aryl" in "optionally substituted aryl" includes, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, More preferably, it is an aryl having 6 to 12 carbon atoms.

Specific examples of "aryl" include phenyl, which is a monocyclic aryl, (2-,3-,4-)biphenylyl, which is a bicyclic aryl, and (1-,2-)naphthyl, which is a fused bicyclic aryl. , tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o -terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl -2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl) , fused tricyclic aryl, acenaphthylene-(1-,3-,4-,5-)yl, fluoren-(1-,2-,3-,4-,9-)yl, phenalene-(1 -,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, tetracyclic aryl quaterphenylyl (5'-phenyl-m-terphenyl-2-yl), 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), fused tetracyclic aryl triphenylene-(1-,2 -)yl, pyrene-(1-,2-,4-)yl, naphthacen-(1-,2-,5-)yl, perylene-(1-,2-,3-) which is a fused pentacyclic aryl )yl, pentacen-(1-,2-,5-,6-)yl, and the like.

Examples of "heteroaryl" in "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, and heteroaryl having 2 to 20 carbon atoms. Aryl is more preferred, heteroaryl having 2 to 15 carbon atoms is even more preferred, and heteroaryl having 2 to 10 carbon atoms is particularly preferred. Examples of the heteroaryl include, for example, a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

Specific heteroaryls include, for example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, Benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, napthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, Phenazacylinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, benzophosphole Examples include a monovalent group of an oxide ring, a monovalent group of a dibenzophosphole oxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzindolocarbazolyl, and benzobenzoindolocarbazolyl.

Further, at least one hydrogen in the above aryl and heteroaryl may be substituted, for example, each may be substituted with the above aryl or heteroaryl.

The carbazole derivative may be a multimer in which a plurality of compounds represented by the above formula (ETM-9) are bonded through a single bond or the like. In this case, in addition to a single bond, they may be bonded through an aryl ring (preferably a polyvalent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring).

Specific examples of this carbazole derivative include the following compounds.

This carbazole derivative can be produced using known raw materials and known synthesis methods.

<Triazine derivative>
The triazine derivative is, for example, a compound represented by the following formula (ETM-10), preferably a compound represented by the following formula (ETM-10-1). Details are described in US Publication No. 2011/0156013.

Each Ar is independently an optionally substituted aryl or an optionally substituted heteroaryl. n is an integer from 1 to 3, preferably 2 or 3.

"Aryl" in "optionally substituted aryl" includes, for example, aryl having 6 to 30 carbon atoms, preferably aryl having 6 to 24 carbon atoms, more preferably aryl having 6 to 20 carbon atoms, More preferably, it is an aryl having 6 to 12 carbon atoms.

Specific examples of "aryl" include phenyl, which is a monocyclic aryl, (2-,3-,4-)biphenylyl, which is a bicyclic aryl, and (1-,2-)naphthyl, which is a fused bicyclic aryl. , tricyclic aryl terphenylyl (m-terphenyl-2'-yl, m-terphenyl-4'-yl, m-terphenyl-5'-yl, o-terphenyl-3'-yl, o -terphenyl-4'-yl, p-terphenyl-2'-yl, m-terphenyl-2-yl, m-terphenyl-3-yl, m-terphenyl-4-yl, o-terphenyl -2-yl, o-terphenyl-3-yl, o-terphenyl-4-yl, p-terphenyl-2-yl, p-terphenyl-3-yl, p-terphenyl-4-yl) , fused tricyclic aryl, acenaphthylene-(1-,3-,4-,5-)yl, fluoren-(1-,2-,3-,4-,9-)yl, phenalene-(1 -,2-)yl, (1-,2-,3-,4-,9-)phenanthryl, tetracyclic aryl quaterphenylyl (5'-phenyl-m-terphenyl-2-yl), 5'-phenyl-m-terphenyl-3-yl, 5'-phenyl-m-terphenyl-4-yl, m-quaterphenylyl), fused tetracyclic aryl triphenylene-(1-,2 -)yl, pyrene-(1-,2-,4-)yl, naphthacen-(1-,2-,5-)yl, perylene-(1-,2-,3-) which is a fused pentacyclic aryl )yl, pentacen-(1-,2-,5-,6-)yl, and the like.

Examples of "heteroaryl" in "optionally substituted heteroaryl" include heteroaryl having 2 to 30 carbon atoms, preferably heteroaryl having 2 to 25 carbon atoms, and heteroaryl having 2 to 20 carbon atoms. Aryl is more preferred, heteroaryl having 2 to 15 carbon atoms is even more preferred, and heteroaryl having 2 to 10 carbon atoms is particularly preferred. Examples of the heteroaryl include, for example, a heterocycle containing 1 to 5 heteroatoms selected from oxygen, sulfur, and nitrogen in addition to carbon as ring constituent atoms.

Specific heteroaryls include, for example, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, pyrazolyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, 1H-indazolyl, Benzimidazolyl, benzoxazolyl, benzothiazolyl, 1H-benzotriazolyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, napthyridinyl, purinyl, pteridinyl, carbazolyl, acridinyl, phenoxathiinyl, phenoxazinyl, phenothiazinyl, phenazinyl, Phenazacylinyl, indolizinyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, naphthobenzofuranyl, thiophenyl, benzothiophenyl, dibenzothiophenyl, naphthobenzothiophenyl, benzophosphoryl, dibenzophosphoryl, benzophosphole Examples include a monovalent group of an oxide ring, a monovalent group of a dibenzophosphole oxide ring, furazanyl, thianthrenyl, indolocarbazolyl, benzindolocarbazolyl, and benzobenzoindolocarbazolyl.

Further, at least one hydrogen in the above aryl and heteroaryl may be substituted, for example, each may be substituted with the above aryl or heteroaryl.

Specific examples of this triazine derivative include the following compounds.

This triazine derivative can be produced using known raw materials and known synthesis methods.

<Benzimidazole derivative>
The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11).

φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is an integer of 1 to 4; "benzimidazole substituent" means that the pyridyl group in the "pyridine substituent" in the above formula (ETM-2), formula (ETM-2-1) and formula (ETM-2-2) is It is a substituent substituted for an imidazole group, and at least one hydrogen in the benzimidazole derivative may be substituted with deuterium. * in the following structural formula represents the bonding position.

R ¹¹ in the above benzimidazole group is hydrogen, alkyl having 1 to 24 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, or aryl having 6 to 30 carbon atoms, and the above formula (ETM-2-1) and formula ( The explanation of R ¹¹ in ETM-2-2) can be cited.

Further, φ is preferably an anthracene ring or a fluorene ring, and the structure in this case can be cited from the explanation for the above formula (ETM-2-1) or formula (ETM-2-2), and each For R ¹¹ to R ¹⁸ in the formula, the explanation for the above formula (ETM-2-1) or formula (ETM-2-2) can be cited. In addition, although the above formula (ETM-2-1) or formula (ETM-2-2) is explained in a form in which two pyridine-based substituents are bonded, when replacing these with benzimidazole-based substituents, both The pyridine substituent may be replaced with a benzimidazole substituent (i.e. n = 2), or one pyridine substituent may be replaced with a benzimidazole substituent and the other pyridine substituent may be replaced with R ¹¹ ~R ¹⁸ (ie n=1). Furthermore, for example, at least one of R ¹¹ to R ¹⁸ in the above formula (ETM-2-1) may be replaced with a benzimidazole substituent, and the "pyridine substituent" may be replaced with R ¹¹ to R ¹⁸ .

Specific examples of this benzimidazole derivative include 1-phenyl-2-(4-(10-phenylanthracen-9-yl)phenyl)-1H-benzo[d]imidazole, 2-(4-(10-( naphthalen-2-yl)anthracen-9-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 2-(3-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl) -1-phenyl-1H-benzo[d]imidazole, 5-(10-(naphthalen-2-yl)anthracen-9-yl)-1,2-diphenyl-1H-benzo[d]imidazole, 1-(4 -(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)-2-phenyl-1H-benzo[d]imidazole, 2-(4-(9,10-di(naphthalen-2-yl)) anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole, 1-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-2- Examples include phenyl-1H-benzo[d]imidazole, 5-(9,10-di(naphthalen-2-yl)anthracen-2-yl)-1,2-diphenyl-1H-benzo[d]imidazole, and the like.

This benzimidazole derivative can be produced using known raw materials and known synthesis methods.

<Phenanthroline derivative>
The phenanthroline derivative is, for example, a compound represented by the following formula (ETM-12) or formula (ETM-12-1). Details are described in International Publication No. 2006/021982.

φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring or triphenylene ring), and n is an integer of 1 to 4; be.

R ¹¹ to R ¹⁸ in each formula are each independently hydrogen, alkyl (preferably alkyl having 1 to 24 carbon atoms), cycloalkyl (preferably cycloalkyl having 3 to 12 carbon atoms), or aryl (preferably carbon aryl number 6 to 30). Further, in the above formula (ETM-12-1), any one of R ¹¹ to R ¹⁸ is bonded to φ, which is an aryl ring.

At least one hydrogen in each phenanthroline derivative may be replaced with deuterium.

As for the alkyl, cycloalkyl and aryl in R ¹¹ to R ¹⁸ , the explanation of R ¹¹ to R ¹⁸ in the above formula (ETM-2) can be cited. Further, in addition to the above-mentioned examples, φ may have the following structural formula, for example. Note that R in the following structural formula is each independently hydrogen, methyl, ethyl, isopropyl, cyclohexyl, phenyl, 1-naphthyl, 2-naphthyl, biphenylyl, or terphenylyl. Moreover, * in each structural formula represents a bonding position.

Specific examples of this phenanthroline derivative include 4,7-diphenyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 9,10-di(1,10- phenanthrolin-2-yl)anthracene, 2,6-di(1,10-phenanthrolin-5-yl)pyridine, 1,3,5-tri(1,10-phenanthrolin-5-yl)benzene, 9,9' -difluoro-bi(1,10-phenanthrolin-5-yl), bathocuproine, 1,3-bis(2-phenyl-1,10-phenanthrolin-9-yl)benzene and compounds represented by the following structural formula, etc. Can be mentioned.

This phenanthroline derivative can be produced using known raw materials and known synthesis methods.

式中、Ｒ^１～Ｒ^６は、それぞれ独立して、水素、フッ素、アルキル、シクロアルキル、アラルキル、アルケニル、シアノ、アルコキシまたはアリールであり、ＭはＬｉ、Ａｌ、Ｇａ、ＢｅまたはＺｎであり、ｎは１～３の整数である。 <Quinolinol metal complex>
The quinolinol metal complex is, for example, a compound represented by the following general formula (ETM-13).

where R ¹ to R ⁶ are each independently hydrogen, fluorine, alkyl, cycloalkyl, aralkyl, alkenyl, cyano, alkoxy or aryl, and M is Li, Al, Ga, Be or Zn; n is an integer from 1 to 3.

Specific examples of quinolinol metal complexes include lithium 8-quinolinol, tris(8-quinolinolate)aluminum, tris(4-methyl-8-quinolinolate)aluminum, tris(5-methyl-8-quinolinolate)aluminum, tris(3 ,4-dimethyl-8-quinolinolate)aluminum, tris(4,5-dimethyl-8-quinolinolate)aluminum, tris(4,6-dimethyl-8-quinolinolate)aluminum, bis(2-methyl-8-quinolinolate)( phenolate)aluminum, bis(2-methyl-8-quinolinolate)(2-methylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3-methylphenolate)aluminum, bis(2-methyl-8- quinolinolate) (4-methylphenolate) aluminum, bis(2-methyl-8-quinolinolate) (2-phenylphenolate) aluminum, bis(2-methyl-8-quinolinolate) (3-phenylphenolate) aluminum, bis (2-Methyl-8-quinolinolate)(4-phenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,3-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)( 2,6-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3,4-dimethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(3,5-dimethylphenolate) Aluminum, bis(2-methyl-8-quinolinolate)(3,5-di-t-butylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,6-diphenylphenolate)aluminum, bis( 2-Methyl-8-quinolinolate)(2,4,6-triphenylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(2,4,6-trimethylphenolate)aluminum, bis(2-methyl -8-quinolinolate)(2,4,5,6-tetramethylphenolate)aluminum, bis(2-methyl-8-quinolinolate)(1-naphthlate)aluminum, bis(2-methyl-8-quinolinolate)(2 -naphthorate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(2-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(3-phenylphenolate)aluminum, bis(2-dimethyl-8-quinolinolate)(3-phenylphenolate)aluminum, ,4-dimethyl-8-quinolinolate)(4-phenylphenolate)aluminum, bis(2,4-dimethyl-8-quinolinolate)(3,5-dimethylphenolate)aluminum, bis(2,4-dimethyl-8 -quinolinolate)(3,5-di-t-butylphenolate)aluminum, bis(2-methyl-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-8-quinolinolate)aluminum, bis(2, 4-dimethyl-8-quinolinolate)aluminum-μ-oxo-bis(2,4-dimethyl-8-quinolinolate)aluminum, bis(2-methyl-4-ethyl-8-quinolinolate)aluminum-μ-oxo-bis( 2-methyl-4-ethyl-8-quinolinolate) aluminum, bis(2-methyl-4-methoxy-8-quinolinolate) aluminum-μ-oxo-bis(2-methyl-4-methoxy-8-quinolinolate) aluminum, Bis(2-methyl-5-cyano-8-quinolinolate)aluminum-μ-oxo-bis(2-methyl-5-cyano-8-quinolinolate)aluminum, bis(2-methyl-5-trifluoromethyl-8- Quinolinolate) aluminum-μ-oxo-bis(2-methyl-5-trifluoromethyl-8-quinolinolate) aluminum, bis(10-hydroxybenzo[h]quinoline) beryllium, and the like.

This quinolinol metal complex can be produced using known raw materials and known synthesis methods.

ベンゾチアゾール誘導体は、例えば下記式（ＥＴＭ－１４－２）で表される化合物である。

<Thiazole derivatives and benzothiazole derivatives>
The thiazole derivative is, for example, a compound represented by the following formula (ETM-14-1).

The benzothiazole derivative is, for example, a compound represented by the following formula (ETM-14-2).

In each formula, φ is an n-valent aryl ring (preferably an n-valent benzene ring, naphthalene ring, anthracene ring, fluorene ring, benzofluorene ring, phenalene ring, phenanthrene ring, or triphenylene ring), and n is 1 to 4. is an integer of "thiazole-based substituent" and "benzothiazole-based substituent" in the above formula (ETM-2), formula (ETM-2-1) and formula (ETM-2-2). The pyridyl group in "Substituent" is a substituent substituted for the following thiazole group or benzothiazole group, and at least one hydrogen in the thiazole derivative and benzothiazole derivative may be substituted with deuterium. * in the following structural formula represents the bonding position.

Further, φ is preferably an anthracene ring or a fluorene ring, and the structure in this case can be cited from the explanation for the above formula (ETM-2-1) or formula (ETM-2-2), and each For R ¹¹ to R ¹⁸ in the formula, the explanation for the above formula (ETM-2-1) or formula (ETM-2-2) can be cited. In addition, although the above formula (ETM-2-1) or formula (ETM-2-2) is explained in a form in which two pyridine-based substituents are bonded, these are replaced by a thiazole-based substituent (or benzothiazole-based substituent). group), both pyridine-based substituents may be replaced with a thiazole-based substituent (or benzothiazole-based substituent) (i.e., n = 2), or any one pyridine-based substituent may be replaced with a thiazole-based substituent. (or benzothiazole-based substituent) and the other pyridine-based substituent may be replaced with R ¹¹ to R ¹⁸ (ie, n=1). Further, for example, by replacing at least one of R ¹¹ to R ¹⁸ in the above formula (ETM-2-1) with a thiazole substituent (or benzothiazole substituent), the "pyridine substituent" can be replaced with R ¹¹ to R ¹⁸ You can also replace it with

These thiazole derivatives or benzothiazole derivatives can be produced using known raw materials and known synthesis methods.

The electron transport layer or the electron injection layer may further contain a substance that can reduce the material forming the electron transport layer or the electron injection layer. A variety of substances can be used as this reducing substance as long as it has a certain reducing property, such as alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, and alkali metals. From the group consisting of earth metal oxides, alkaline earth metal halides, rare earth metal oxides, rare earth metal halides, alkali metal organic complexes, alkaline earth metal organic complexes, and rare earth metal organic complexes At least one selected can be suitably used.

Preferred reducing substances include alkali metals such as Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV), or Cs (work function: 1.95 eV), and Ca (work function: 2.3 eV). 9 eV), Sr (2.0 to 2.5 eV), or Ba (2.52 eV), and substances with a work function of 2.9 eV or less are particularly preferred. Among these, more preferable reducing substances are alkali metals such as K, Rb, or Cs, still more preferably Rb or Cs, and most preferable is Cs. These alkali metals have particularly high reducing ability, and by adding a relatively small amount to the material forming the electron transport layer or the electron injection layer, the luminance of the organic EL element can be improved and the life of the organic EL element can be extended. Further, as a reducing substance with a work function of 2.9 eV or less, a combination of two or more of these alkali metals is also preferable, and in particular, a combination containing Cs, such as Cs and Na, Cs and K, Cs and Rb, or A combination of Cs, Na and K is preferred. By including Cs, the reducing ability can be efficiently exhibited, and by adding it to the material forming the electron transport layer or the electron injection layer, the luminance of light emission and the longevity of the organic EL element can be improved.

The materials for the electron transport injection layer and the material for the electron transport layer described above are polymer compounds obtained by polymerizing reactive compounds substituted with reactive substituents as monomers, or crosslinked polymers thereof, or A pendant polymer compound obtained by reacting a chain polymer with the above-mentioned reactive compound, or a pendant polymer crosslinked product thereof, can also be used as an electronic layer material. As for the reactive substituent in this case, the explanation for the polycyclic aromatic compound represented by formula (1) or formula (2) can be cited.
Details of the uses of such polymer compounds and crosslinked polymers will be described later.

<Cathode in organic electroluminescent device>
The cathode 108 serves to inject electrons into the light emitting layer 105 via the electron injection layer 107 and the electron transport layer 106.

The material forming the cathode 108 is not particularly limited as long as it can efficiently inject electrons into the organic layer, but the same material as the material forming the anode 102 can be used. Among them, metals such as tin, indium, calcium, aluminum, silver, copper, nickel, chromium, gold, platinum, iron, zinc, lithium, sodium, potassium, cesium, and magnesium, or their alloys (magnesium-silver alloy, magnesium - indium alloys, aluminum-lithium alloys such as lithium fluoride/aluminum), etc.) are preferred. In order to increase electron injection efficiency and improve device characteristics, lithium, sodium, potassium, cesium, calcium, magnesium, or alloys containing these low work function metals are effective. However, these low work function metals are generally unstable in the atmosphere. In order to improve this point, a method is known in which, for example, the organic layer is doped with a trace amount of lithium, cesium, or magnesium to use a highly stable electrode. Other dopants that can also be used are inorganic salts such as lithium fluoride, cesium fluoride, lithium oxide, and cesium oxide. However, it is not limited to these.

Additionally, metals such as platinum, gold, silver, copper, iron, tin, aluminum and indium, or alloys of these metals, as well as inorganic materials such as silica, titania and silicon nitride, polyvinyl alcohol, and vinyl chloride, are used to protect the electrodes. A preferred example is to laminate a hydrocarbon-based polymer compound or the like. The method for producing these electrodes is not particularly limited as long as conduction can be achieved, such as resistance heating, electron beam evaporation, sputtering, ion plating, and coating.

<Binders that may be used in each layer>
The above materials used for the hole injection layer, hole transport layer, light emitting layer, electron transport layer and electron injection layer can be used alone to form each layer, but polyvinyl chloride, polycarbonate, Polystyrene, poly(N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, ABS resin, polyurethane resin It can also be used by dispersing it in solvent-soluble resins such as phenol resins, xylene resins, petroleum resins, urea resins, melamine resins, unsaturated polyester resins, alkyd resins, epoxy resins, and curable resins such as silicone resins. be.

<Method for manufacturing organic electroluminescent device>
Each layer constituting an organic EL element is formed into a thin film using a method such as evaporation, resistance heating evaporation, electron beam evaporation, sputtering, molecular lamination, printing, spin coating, casting, or coating. By doing so, it can be formed. The thickness of each layer formed in this way is not particularly limited and can be set appropriately depending on the properties of the material, but is usually in the range of 2 nm to 5000 nm. The film thickness can usually be measured using a crystal oscillation type film thickness measuring device. When forming a thin film using an evaporation method, the evaporation conditions vary depending on the type of material, the intended crystal structure and association structure of the film, and so on. Generally, the deposition conditions are: boat heating temperature +50 to +400°C, vacuum degree 10 ^-6 to 10 ^-3 Pa, deposition rate 0.01 to 50 nm/sec, substrate temperature -150 to +300°C, and film thickness 2 nm to 5 μm. It is preferable to set it appropriately within a range.

When applying a direct current voltage to the organic EL element obtained in this way, it is sufficient to apply it with the anode as + polarity and the cathode as - polarity. Luminescence can be observed from the sides (anode or cathode, or both). This organic EL element also emits light when pulsed current or alternating current is applied. Note that the waveform of the applied alternating current may be arbitrary.

Next, as an example of a method for producing an organic EL device, an organic EL device consisting of an anode/hole injection layer/hole transport layer/light emitting layer made of a host material and dopant material/electron transport layer/electron injection layer/cathode will be described. The manufacturing method will be explained.

<Vapor deposition method>
After a thin film of an anode material is formed on a suitable substrate by vapor deposition or the like to produce an anode, thin films of a hole injection layer and a hole transport layer are formed on this anode. On top of this, a host material and a dopant material are co-deposited to form a thin film to form a light-emitting layer, an electron transport layer and an electron injection layer are formed on this light-emitting layer, and a thin film of a cathode material is further formed by vapor deposition or the like. By forming it and using it as a cathode, the desired organic EL element can be obtained. In addition, in the production of the above-mentioned organic EL element, it is also possible to reverse the production order and produce the cathode, electron injection layer, electron transport layer, light emitting layer, hole transport layer, hole injection layer, and anode in this order. It is.

<Wet film formation method>
The wet film-forming method is carried out by preparing a liquid organic layer-forming composition containing a low-molecular compound capable of forming each organic layer of an organic EL element. If there is no suitable organic solvent to dissolve this low-molecular-weight compound, the low-molecular-weight compound is substituted with a reactive substituent and becomes a polymer together with other monomers and main chain polymers that have a solubility function. The composition for forming an organic layer may be prepared from a molecularized polymer compound or the like.

In the wet film forming method, a coating film is generally formed through a coating step of applying an organic layer-forming composition to a substrate and a drying step of removing a solvent from the applied organic layer-forming composition. When the polymer compound has a crosslinkable substituent (also referred to as a crosslinkable polymer compound), it is further crosslinked through this drying step to form a crosslinked polymer. Depending on the difference in coating process, the method using a spin coater is the spin coating method, the method using a slit coater is the slit coating method, the method using a plate is gravure, offset, reverse offset, flexo printing method, and the method using an inkjet printer is the inkjet method. The method of spraying in a mist is called the spray method. The drying process includes methods such as air drying, heating, and reduced pressure drying. The drying step may be performed only once, or may be performed multiple times using different methods and conditions. Further, different methods may be used in combination, for example, calcination under reduced pressure.

The wet film forming method is a film forming method using a solution, and includes, for example, some printing methods (inkjet method), spin coating method, casting method, coating method, and the like. Unlike the vacuum evaporation method, the wet film formation method does not require the use of an expensive vacuum evaporation device and can form a film under atmospheric pressure. In addition, the wet film formation method allows for large-area production and continuous production, leading to reductions in manufacturing costs.

On the other hand, when compared with the vacuum evaporation method, the wet film formation method may have difficulty in laminating layers. When producing a laminated film using a wet film formation method, it is necessary to prevent the composition of the upper layer from dissolving the lower layer. solvents) are used. However, even with these techniques, it may be difficult to use a wet film formation method for coating all films.

Therefore, a method is generally adopted in which an organic EL element is fabricated using a wet film forming method for only some layers and using a vacuum evaporation method for the remaining layers.

For example, a procedure for manufacturing an organic EL element by partially applying a wet film forming method is shown below.
(Procedure 1) Film formation by vacuum evaporation of anode (Procedure 2) Film formation by wet film formation of hole injection layer forming composition containing material for hole injection layer (Procedure 3) Material for hole transport layer Forming a film by a wet film forming method of a composition for forming a hole transport layer containing a host material and a dopant material (Step 4) Forming a film by a wet film forming method of a composition for forming a light emitting layer containing a host material and a dopant material (Step 5) Electron transport layer Film formation by vacuum evaporation method (Step 6) Electron injection layer film formation by vacuum evaporation method (Step 7) Film formation by vacuum evaporation method of cathode By going through this procedure, the anode/hole injection layer/hole transport An organic EL device consisting of a layer/a light-emitting layer made of a host material and a dopant material/an electron transport layer/an electron injection layer/a cathode is obtained.
Of course, there are ways to prevent the underlying light-emitting layer from dissolving, or to form a layer containing the material for the electron transport layer and the material for the electron injection layer by using a method that forms the film from the cathode side, contrary to the above procedure. A film can be formed using a wet film forming method.

<Other film formation methods>
Laser thermal lithography (LITI) can be used to form a film from the composition for forming an organic layer. LITI is a method in which a compound attached to a base material is heated and vapor-deposited using a laser, and an organic layer-forming composition can be used as the material applied to the base material.

<Optional process>
Appropriate treatment steps, cleaning steps, and drying steps may be performed as appropriate before and after each step of film formation. Examples of the treatment step include exposure treatment, plasma surface treatment, ultrasonic treatment, ozone treatment, cleaning treatment using an appropriate solvent, heat treatment, and the like. Furthermore, a series of steps for producing a bank may also be mentioned.

Photolithography technology can be used to create the banks. As bank materials that can be used in photolithography, positive resist materials and negative resist materials can be used. Patternable printing methods such as inkjet printing, gravure offset printing, reverse offset printing, and screen printing can also be used. In this case, a permanent resist material can also be used.

Materials used for banks include polysaccharides and their derivatives, homopolymers and copolymers of hydroxyl-containing ethylenic monomers, biopolymer compounds, polyacryloyl compounds, polyesters, polystyrene, polyimides, polyamideimides, and polyetherimides. , polysulfide, polysulfone, polyphenylene, polyphenyl ether, polyurethane, epoxy (meth)acrylate, melamine (meth)acrylate, polyolefin, cyclic polyolefin, acrylonitrile-butadiene-styrene copolymer (ABS), silicone resin, polyvinyl chloride, chlorine Examples include fluorinated polyethylene, chlorinated polypropylene, polyacetate, polynorbornene, synthetic rubber, polyfluorovinylidene, polytetrafluoroethylene, polyhexafluoropropylene and other fluorinated polymers, fluoroolefin-hydrocarbon olefin copolymers, and fluorocarbon polymers. However, it is not limited to that.

<Organic layer forming composition used in wet film forming method>
The composition for forming an organic layer is obtained by dissolving in an organic solvent a low-molecular compound capable of forming each organic layer of an organic EL element, or a high-molecular compound obtained by polymerizing the low-molecular compound. For example, the composition for forming a light emitting layer includes a polycyclic aromatic compound (or its polymer compound) which is at least one dopant material as a first component, at least one host material as a second component, and a third component. It contains at least one organic solvent as a component. The first component functions as a dopant component of the emissive layer obtained from the composition, and the second component functions as the host component of the emissive layer. The third component functions as a solvent that dissolves the first and second components in the composition, and provides a smooth and uniform surface shape during application due to the controlled evaporation rate of the third component itself.

<Organic solvent>
The composition for forming an organic layer contains at least one kind of organic solvent. By controlling the evaporation rate of the organic solvent during film formation, it is possible to control and improve film formability, the presence or absence of defects in the coating, surface roughness, and smoothness. Furthermore, when forming a film using an inkjet method, it is possible to control meniscus stability in a pinhole of an inkjet head and to control and improve ejection performance. In addition, by controlling the drying rate of the film and the orientation of the derivative molecules, it is possible to improve the electrical properties, luminescence properties, efficiency, and life of an organic EL device having an organic layer obtained from the composition for forming an organic layer. I can do it.

(1) Physical properties of organic solvent The boiling point of at least one organic solvent is 130°C to 300°C, more preferably 140°C to 270°C, even more preferably 150°C to 250°C. When the boiling point is higher than 130° C., it is preferable from the viewpoint of inkjet ejection properties. Moreover, when the boiling point is lower than 300° C., it is preferable from the viewpoint of coating film defects, surface roughness, residual solvent, and smoothness. The organic solvent preferably contains two or more types of organic solvents from the viewpoint of good inkjet ejection properties, film formability, smoothness, and low residual solvent. On the other hand, depending on the case, the composition may be made into a solid state by removing the solvent from the organic layer forming composition in consideration of transportability and the like.

Furthermore, the organic solvent includes a good solvent (GS) and a poor solvent (PS) for at least one solute, and the boiling point (BP _GS ) of the good solvent (GS) is lower than the boiling point (BP _PS ) of the poor solvent (PS). Particularly preferred are configurations in which the
By adding a poor solvent with a high boiling point, the good solvent with a low boiling point evaporates first during film formation, increasing the concentration of the substances contained in the composition and the concentration of the poor solvent, thereby promoting rapid film formation. As a result, a highly smooth coating film with few defects and low surface roughness can be obtained.

The difference in solubility (S _GS −S _PS ) is preferably 1% or more, more preferably 3% or more, and even more preferably 5% or more. The difference in boiling points (BP _PS -BP _GS ) is preferably 10°C or more, more preferably 30°C or more, and even more preferably 50°C or more.

After film formation, the organic solvent is removed from the coating film through a drying process such as vacuum, reduced pressure, or heating. When heating is performed, it is preferable to perform the heating at a temperature not higher than the glass transition temperature (Tg) of at least one of the solutes +30° C. from the viewpoint of improving coating film formation properties. Furthermore, from the viewpoint of reducing residual solvent, it is preferable to heat at least one of the solutes at a glass transition point (Tg) of −30° C. or higher. Even if the heating temperature is lower than the boiling point of the organic solvent, the organic solvent can be sufficiently removed because the film is thin. Further, drying may be performed multiple times at different temperatures, and multiple drying methods may be used in combination.

(2) Specific examples of organic solvents Examples of organic solvents used in the organic layer forming composition include alkylbenzene solvents, phenyl ether solvents, alkyl ether solvents, cyclic ketone solvents, aliphatic ketone solvents, and monocyclic solvents. Examples include ketone solvents, solvents having a diester skeleton, and fluorine-containing solvents. Specific examples include pentanol, hexanol, heptanol, octanol, nonanol, decanol, undecanol, dodecanol, tetradecanol, hexan-2-ol, Heptane-2-ol, octan-2-ol, decan-2-ol, dodecane-2-ol, cyclohexanol, α-terpineol, β-terpineol, γ-terpineol, δ-terpineol, terpineol (mixture), ethylene glycol Monomethyl ether acetate, propylene glycol monomethyl ether acetate, diethylene glycol dimethyl ether, dipropylene glycol dimethyl ether, diethylene glycol ethyl methyl ether, diethylene glycol isopropyl methyl ether, dipropylene glycol monomethyl ether, diethylene glycol diethyl ether, diethylene glycol monomethyl ether, diethylene glycol butyl methyl ether, tripropylene glycol Dimethyl ether, triethylene glycol dimethyl ether, diethylene glycol monobutyl ether, ethylene glycol monophenyl ether, triethylene glycol monomethyl ether, diethylene glycol dibutyl ether, triethylene glycol butyl methyl ether, polyethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, p-xylene, m-xylene , o-xylene, 2,6-lutidine, 2-fluoro-m-xylene, 3-fluoro-o-xylene, 2-chlorobenzotrifluoride, cumene, toluene, 2-chloro-6-fluorotoluene, 2-fluoro Anisole, anisole, 2,3-dimethylpyrazine, bromobenzene, 4-fluoroanisole, 3-fluoroanisole, 3-trifluoromethylanisole, mesitylene, 1,2,4-trimethylbenzene, t-butylbenzene, 2-methyl Anisole, phenethole, benzodioxole, 4-methylanisole, s-butylbenzene, 3-methylanisole, 4-fluoro-3-methylanisole, cymene, 1,2,3-trimethylbenzene, 1,2-dichlorobenzene , 2-fluorobenzonitrile, 4-fluoroberatrol, 2,6-dimethylanisole, n-butylbenzene, 3-fluorobenzonitrile, decalin (decahydronaphthalene), neopentylbenzene, 2,5-dimethylanisole, 2 , 4-dimethylanisole, benzonitrile, 3,5-dimethylanisole, diphenyl ether, 1-fluoro-3,5-dimethoxybenzene, methyl benzoate, isopentylbenzene, 3,4-dimethylanisole, o-tolnitrile, n- Amylbenzene, veratrol, 1,2,3,4-tetrahydronaphthalene, ethyl benzoate, n-hexylbenzene, propyl benzoate, cyclohexylbenzene, 1-methylnaphthalene, butyl benzoate, 2-methylbiphenyl, 3-phenoxytoluene , 2,2'-bitryl, dodecylbenzene, dipentylbenzene, tetramethylbenzene, trimethoxybenzene, trimethoxytoluene, 2,3-dihydrobenzofuran, 1-methyl-4-(propoxymethyl)benzene, 1-methyl-4 -(Butyloxymethyl)benzene, 1-methyl-4-(pentyloxymethyl)benzene, 1-methyl-4-(hexyloxymethyl)benzene, 1-methyl-4-(heptyloxymethyl)benzene benzyl butyl ether, benzyl Examples include, but are not limited to, pentyl ether, benzylhexyl ether, benzylheptyl ether, benzyl octyl ether, and the like. Moreover, a single solvent may be used or a mixture may be used.

<Optional ingredients>
The composition for forming an organic layer may contain optional components within a range that does not impair its properties. Optional components include binders, surfactants, and the like.

(1) Binder The composition for forming an organic layer may contain a binder. The binder forms a film during film formation and also bonds the obtained film to the substrate. It also plays a role in dissolving, dispersing, and binding other components in the composition for forming an organic layer.

Examples of the binder used in the organic layer forming composition include acrylic resin, polyethylene terephthalate, ethylene-vinyl acetate copolymer, ethylene-vinyl alcohol copolymer, acrylonitrile-ethylene-styrene copolymer (AES) resin, Ionomer, chlorinated polyether, diallyl phthalate resin, unsaturated polyester resin, polyethylene, polypropylene, polyvinyl chloride, polyvinylidene chloride, polystyrene, polyvinyl acetate, Teflon, acrylonitrile-butadiene-styrene copolymer (ABS) resin, acrylonitrile - styrene copolymer (AS) resins, phenolic resins, epoxy resins, melamine resins, urea resins, alkyd resins, polyurethanes, and copolymers of the above resins and polymers.

The number of binders used in the composition for forming an organic layer may be one type or a mixture of multiple types may be used.

(2) Surfactant The composition for forming an organic layer may contain a surfactant, for example, to control the film surface uniformity, solvent affinity and liquid repellency of the film surface. Good too. Surfactants are classified into ionic and nonionic based on the structure of their hydrophilic groups, and further classified into alkyl-based, silicon-based, and fluorine-based based on the structure of their hydrophobic groups. In addition, based on the structure of the molecule, it is classified into monomolecular systems with a relatively small molecular weight and a simple structure, and polymer systems with a large molecular weight and side chains and branches. Also, based on the composition, they are classified into single type and mixed type, which is a mixture of two or more types of surfactants and base materials. As the surfactant that can be used in the composition for forming an organic layer, all kinds of surfactants can be used.

As the surfactant, for example, Polyflow No. 45, Polyflow KL-245, Polyflow No. 75, Polyflow No. 90, Polyflow No. 95 (product name, manufactured by Kyoeisha Chemical Industry Co., Ltd.), Disperbyk 161, Disperbyk 162, Disperbake 163, Disperbake 164, Disperbake 166, Disperbake 170, Disperbyk 180, Disperbake 181, Disperbyk Bake 182, BYK300, BYK306, BYK310, BYK320, BYK330, BYK342, BYK344, BYK346 (product name, manufactured by BYK Chemie Japan Co., Ltd.), KP-341, KP-358, KP-368, KF-96-50CS, KF -50-100CS (trade name, manufactured by Shin-Etsu Chemical Co., Ltd.), Surflon SC-101, Surflon KH-40 (trade name, manufactured by Seimi Chemical Co., Ltd.), Ftergent 222F, Ftergent 251, FTX-218 ( EFTOP EF-351, EFTOP EF-352, EFTOP EF-601, EFTOP EF-801, EFTOP EF-802 (product name, manufactured by Mitsubishi Materials Corporation), Megafac F- 470, Megafac F-471, Megafac F-475, Megafac R-08, Megafac F-477, Megafac F-479, Megafac F-553, Megafac F-554 (product name, DIC Corporation) ), fluoroalkyl benzene sulfonate, fluoroalkyl carboxylate, fluoroalkyl polyoxyethylene ether, fluoroalkylammonium iodide, fluoroalkyl betaine, fluoroalkylsulfonate, diglycerine tetrakis (fluoroalkyl polyoxyethylene ether) ), fluoroalkyltrimethylammonium salt, fluoroalkylaminosulfonate, polyoxyethylene nonylphenyl ether, polyoxyethylene octylphenyl ether, polyoxyethylene alkyl ether, polyoxyethylene laurate, polyoxyethylene oleate, polyoxyethylene Stearate, polyoxyethylene laurylamine, sorbitan laurate, sorbitan palmitate, sorbitan stearate, sorbitan oleate, sorbitan fatty acid ester, polyoxyethylene sorbitan laurate, polyoxyethylene sorbitan palmitate, polyoxyethylene sorbitan stearate, Mention may be made of polyoxyethylene sorbitan oleate, polyoxyethylene naphthyl ether, alkylbenzene sulfonates and alkyl diphenyl ether disulfonates.

Moreover, one type of surfactant may be used, or two or more types may be used in combination.

<Composition and physical properties of organic layer forming composition>
The content of each component in the organic layer-forming composition is determined by the good solubility, storage stability and film formability of each component in the organic layer-forming composition, as well as the organic layer-forming composition. Good film quality of the coating film, good ejection properties when using an inkjet method, and good electrical properties, light emitting properties, efficiency, and life of an organic EL device having an organic layer produced using the composition. The decision is made taking into account the following points of view. For example, in the case of a composition for forming a light-emitting layer, the first component is 0.0001% to 2.0% by weight based on the total weight of the composition for forming a light-emitting layer, and the second component is for forming a light-emitting layer. The third component is 0.0999% to 8.0% by weight based on the total weight of the composition, and the third component is 90.0% to 99.9% by weight based on the total weight of the composition for forming a light emitting layer. preferable.

More preferably, the first component is 0.005% to 1.0% by weight based on the total weight of the composition for forming a luminescent layer, and the second component is preferably 0.005% to 1.0% by weight based on the total weight of the composition for forming a luminescent layer. The amount of the third component is 0.095% to 4.0% by weight, and the third component is 95.0% to 99.9% by weight based on the total weight of the composition for forming a light emitting layer. More preferably, the first component is 0.05% to 0.5% by weight based on the total weight of the composition for forming a luminescent layer, and the second component is preferably 0.05% to 0.5% by weight based on the total weight of the composition for forming a luminescent layer. The amount of the third component is 0.25% to 2.5% by weight, and the third component is 97.0% to 99.7% by weight based on the total weight of the composition for forming a light emitting layer.

The composition for forming an organic layer can be produced by appropriately selecting and performing stirring, mixing, heating, cooling, dissolving, dispersing, etc., the above-mentioned components using known methods. Further, after preparation, filtration, degassing (also referred to as degassing), ion exchange treatment, inert gas substitution/enclosure treatment, etc. may be appropriately selected and carried out.

As for the viscosity of the composition for forming an organic layer, the higher the viscosity, the better the film forming property and the better the ejection property when using an inkjet method. On the other hand, the lower the viscosity, the easier it is to form a thin film. From this, the viscosity of the organic layer forming composition at 25° C. is preferably 0.3 to 3 mPa·s, more preferably 1 to 3 mPa·s. In the present invention, the viscosity is a value measured using a cone-plate rotational viscometer (cone-plate type).

As for the surface tension of the composition for forming an organic layer, the lower the surface tension, the better the film formability and the coating film free of defects can be obtained. On the other hand, the higher the value, the better the inkjet ejection performance. From this, the surface tension of the organic layer forming composition at 25° C. is preferably 20 to 40 mN/m, more preferably 20 to 30 mN/m. In the present invention, surface tension is a value measured using a hanging drop method.

式（ＸＬＰ－１）において、
ＭＵｘ、ＥＣｘおよびｋは上記式（ＳＰＨ－１）におけるＭＵ、ＥＣおよびｋと同定義であり、ただし、式（ＸＬＰ－１）で表される化合物は少なくとも１つの架橋性置換基（ＸＬＳ）を有し、好ましくは架橋性置換基を有する１価または２価の芳香族化合物の含有量は、分子中０．１～８０重量％である。 <Crosslinkable polymer compound: compound represented by general formula (XLP-1)>
Next, a case where the above-mentioned polymer compound has a crosslinkable substituent will be explained. Such a crosslinkable polymer compound is, for example, a compound represented by the following general formula (XLP-1).

In formula (XLP-1),
MUx, ECx and k have the same definitions as MU, EC and k in the above formula (SPH-1), provided that the compound represented by formula (XLP-1) has at least one crosslinkable substituent (XLS). The content of the monovalent or divalent aromatic compound, preferably having a crosslinkable substituent, is 0.1 to 80% by weight in the molecule.

The content of the monovalent or divalent aromatic compound having a crosslinkable substituent is preferably 0.5 to 50% by weight, more preferably 1 to 20% by weight.

The crosslinkable substituent (XLS) is not particularly limited as long as it is a group that can further crosslink the above-mentioned polymer compound, but substituents having the following structure are preferred. * in each structural formula indicates the bonding position.

L is each independently a single bond, -O-, -S-, >C=O, -OC(=O)-, alkylene having 1 to 12 carbon atoms, oxyalkylene having 1 to 12 carbon atoms and polyoxyalkylene having 1 to 12 carbon atoms. Among the above substituents, those represented by formula (XLS-1), formula (XLS-2), formula (XLS-3), formula (XLS-9), formula (XLS-10) or formula (XLS-17) are A group represented by formula (XLS-1), formula (XLS-3) or formula (XLS-17) is more preferred.

Examples of the divalent aromatic compound having a crosslinkable substituent include compounds having the following partial structure. * in the following structural formula represents the bonding position.

<Production method of polymer compound and crosslinkable polymer compound>
The method for producing a polymer compound and a crosslinkable polymer compound will be explained using the above-mentioned compound represented by the formula (SPH-1) and the compound represented by (XLP-1) as examples. These compounds can be synthesized by appropriately combining known production methods.

Examples of the solvent used in the reaction include aromatic solvents, saturated/unsaturated hydrocarbon solvents, alcohol solvents, ether solvents, etc. For example, dimethoxyethane, 2-(2-methoxyethoxy)ethane, 2-(2-methoxyethoxy)ethane, -ethoxyethoxy)ethane and the like.

Moreover, the reaction may be carried out in a two-phase system. When the reaction is carried out in a two-phase system, a phase transfer catalyst such as a quaternary ammonium salt may be added, if necessary.

When producing the compound of formula (SPH-1) and the compound of (XLP-1), it may be produced in one step or in multiple steps. Alternatively, it may be carried out by a batch polymerization method in which the reaction is started after all of the raw materials are put into the reaction vessel, or by a dropwise polymerization method in which the raw materials are added dropwise into the reaction vessel, or the product may be added to the reaction vessel to prevent the progress of the reaction. It may be carried out by a precipitation polymerization method that involves precipitation, or it can be synthesized by appropriately combining these methods. For example, when synthesizing a compound represented by formula (SPH-1) in one step, the desired product is obtained by carrying out the reaction with the monomer unit (MU) and end cap unit (EC) added to the reaction vessel. . In addition, when synthesizing the compound represented by the general formula (SPH-1) in multiple steps, the monomer unit (MU) can be polymerized to the desired molecular weight, and then an end cap unit (EC) can be added and reacted. get something If different types of monomer units (MU) are added and reacted in multiple steps, a polymer having a concentration gradient in the structure of the monomer units can be produced. Moreover, after preparing the precursor polymer, the target polymer can be obtained by post-reaction.

Further, by selecting the polymerizable group of the monomer unit (MU), the primary structure of the polymer can be controlled. For example, as shown in Synthesis Schemes 1 to 3, it is possible to synthesize polymers with random primary structures (Synthesis Scheme 1), polymers with regular primary structures (Synthesis Schemes 2 and 3), etc. They can be used in appropriate combinations depending on the object. Furthermore, by using a monomer unit having three or more polymerizable groups, hyperbranched polymers and dendrimers can be synthesized.

Monomer units that can be used in the present invention include JP2010-189630A, WO2012/086671, WO2013/191088, WO2002/045184, and WO2011/049241. International Publication No. 2013/146806, International Publication No. 2005/049546, International Publication No. 2015/145871, JP 2010-215886, JP 2008-106241, WO 2016/031639, It can be synthesized according to the method described in JP-A No. 2011-174062.

For specific polymer synthesis procedures, please refer to JP 2012-036388, WO 2015/008851, JP 2012-36381, JP 2012-144722, WO 2015/194448. , International Publication No. 2013/146806, International Publication No. 2015/145871, International Publication No. 2016/031639, International Publication No. 2016/125560, International Publication No. 2011/049241. I can do it.

<Application examples of organic electroluminescent devices>
Further, the present invention can be applied to a display device equipped with an organic EL element or a lighting device equipped with an organic EL element.
A display device or a lighting device equipped with an organic EL element can be manufactured by a known method such as connecting the organic EL element according to this embodiment with a known drive device, and can be manufactured by a known method such as direct current drive, pulse drive, alternating current drive, etc. It can be driven using a known driving method as appropriate.

Examples of display devices include panel displays such as color flat panel displays, flexible displays such as flexible color organic electroluminescent (EL) displays, etc. (Refer to the official gazette, Japanese Patent Application Laid-open No. 2004-281086, etc.). Furthermore, examples of the display method include a matrix method and/or a segment method. Note that matrix display and segment display may coexist in the same panel.

In a matrix, display pixels are arranged two-dimensionally in a grid or mosaic pattern, and characters or images are displayed as a collection of pixels. The shape and size of pixels are determined by the application. For example, rectangular pixels with sides of 300 μm or less are usually used to display images and characters on computers, monitors, and televisions, and in the case of large displays such as display panels, pixels with sides of mm order are used. become. In the case of monochrome display, pixels of the same color may be arranged, but in the case of color display, red, green, and blue pixels are displayed side by side. In this case, there are typically delta types and striped types. As a driving method for this matrix, either a line sequential driving method or an active matrix driving method may be used. Line sequential driving has the advantage of a simpler structure, but when considering operating characteristics, active matrix driving may be superior in some cases, so it is necessary to use it properly depending on the application.

In the segment method (type), a pattern is formed to display predetermined information, and a predetermined area is caused to emit light. Examples include time and temperature displays on digital clocks and thermometers, operating status displays on audio equipment and electromagnetic cookers, and panel displays on automobiles.

Examples of lighting devices include lighting devices for indoor lighting, backlights for liquid crystal display devices, etc. etc.). Backlights are mainly used for the purpose of improving the visibility of display devices that do not emit light by themselves, and are used in liquid crystal display devices, watches, audio devices, automobile panels, display boards, signs, and the like. In particular, considering that it is difficult to reduce the thickness of liquid crystal display devices, especially backlights for personal computers where thinning is an issue, since conventional systems consist of fluorescent lamps and light guide plates, this embodiment A backlight using a light emitting element according to the above is characterized by being thin and lightweight.

3-2. Other Organic Devices The polycyclic aromatic compound according to the present invention can be used in the production of organic field effect transistors, organic thin film solar cells, wavelength conversion filters, etc., in addition to the above-mentioned organic electroluminescent devices.

An organic field effect transistor is a transistor that controls current by an electric field generated by voltage input, and is provided with a gate electrode in addition to a source electrode and a drain electrode. When a voltage is applied to the gate electrode, an electric field is generated, and the flow of electrons (or holes) flowing between the source and drain electrodes can be arbitrarily blocked and the current can be controlled. Field-effect transistors are easier to miniaturize than simple transistors (bipolar transistors), and are often used as elements constituting integrated circuits and the like.

The structure of an organic field effect transistor is usually such that a source electrode and a drain electrode are provided in contact with an organic semiconductor active layer formed using the polycyclic aromatic compound according to the present invention, and a source electrode and a drain electrode are further provided in contact with the organic semiconductor active layer. A gate electrode may be provided with an insulating layer (dielectric layer) sandwiched therebetween. Examples of the element structure include the following structures.
(1) Substrate/gate electrode/insulator layer/source electrode/drain electrode/organic semiconductor active layer (2) substrate/gate electrode/insulator layer/organic semiconductor active layer/source electrode/drain electrode (3) substrate/organic Semiconductor active layer/source electrode/drain electrode/insulator layer/gate electrode (4) Substrate/source electrode/drain electrode/organic semiconductor active layer/insulator layer/gate electrode The organic field effect transistor configured in this way is It can be applied as a pixel drive switching element for active matrix drive type liquid crystal displays and organic electroluminescent displays.

An organic thin film solar cell has a structure in which an anode such as ITO, a hole transport layer, a photoelectric conversion layer, an electron transport layer, and a cathode are laminated on a transparent substrate such as glass. The photoelectric conversion layer has a p-type semiconductor layer on the anode side and an n-type semiconductor layer on the cathode side. The polycyclic aromatic compound according to the present invention can be used as a material for a hole transport layer, a p-type semiconductor layer, an n-type semiconductor layer, and an electron transport layer, depending on its physical properties. The polycyclic aromatic compound according to the present invention can function as a hole transport material or an electron transport material in an organic thin film solar cell. The organic thin film solar cell may appropriately include a hole blocking layer, an electron blocking layer, an electron injection layer, a hole injection layer, a smoothing layer, etc. in addition to the above. For the organic thin film solar cell, known materials used for organic thin film solar cells can be appropriately selected and used in combination.

Quantum dots with a narrow half-width emission are used as phosphors in wavelength conversion filters to widen the color gamut of displays. On the other hand, there are problems such as instability against oxidation, high agglomeration due to the nano-sized particles, and the metals used are regulated as contaminants. The polycyclic aromatic compound according to the present invention can be used as a phosphor in a wavelength conversion filter. The matrix in which the polycyclic aromatic compound is dispersed is preferably a polymeric material with high transparency, low water vapor permeability, low oxygen permeability, and high thermal stability, such as (meth)acrylate, etc. ) acrylic polymers and cycloolefin polymers such as Zeonex.

EXAMPLES Hereinafter, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited thereto.

<Synthesis example: Synthesis of polycyclic aromatic compound>
[Synthesis example (1): Synthesis of compound (1-1)]

Boron tribromide (0.30 ml, 3.2 mmol) was added to a flask containing compound (I-1) (0.176 g, 0.10 mmol) and o-dichlorobenzene (1.0 ml) at room temperature under a nitrogen atmosphere. ) was added. After the dropwise addition was completed, the mixture was heated to 200°C and stirred for 20 hours. The reaction solution was cooled to room temperature, and hydrogen bromide in the reaction solution was distilled off under reduced pressure. After diluting the reaction solution by adding dichloromethane (50 ml), a phosphate buffer solution (pH=7, 50 ml) was added at room temperature, the aqueous layer was extracted three times with dichloromethane, and then the solvent was distilled off under reduced pressure. The obtained crude product was purified by silica gel short pass (eluent: dichloromethane) and hexane washing to obtain compound (1-1) (60.0 mg, yield 33%) as an orange solid.

The structure of the obtained compound was confirmed by NMR measurement.
¹ H-NMR (400 MHz, CDCl ₃ ): δ = 0.93 (t, 6H), 0.95 (t, 6H), 1.01 (t, 6H), 1.02 (t, 6H), 1 .26 (s, 18H), 1.33-1.40 (m, 16H), 1.42-1.51 (m, 16H), 1.84-1.92 (m, 4H), 2.40 (s, 12H), 2.47 (s, 6H), 2.48 (s, 6H), 2.74-2.86 (m, 4H), 2.98-3.07 (m, 4H), 5.40 (s, 2H), 6.87 (s, 4H), 6.93 (s, 2H), 7.07 (s, 2H), 7.09 (s, 2H), 7.18 (s , 2H), 7.29 (s, 2H), 7.43 (d, 2H), 7.92 (s, 2H), 8.26 (s, 2H), 8.27 (s, 2H), 8 .79 (s, 2H), 8.84 (s, 2H), 9.07 (d, 2H)

[Synthesis example (2): Synthesis of compound (1-2)]

Boron triiodide (0.469 g, 1.2 mmol) was added to a Schlenk containing compound (I-2) (0.126 g, 0.05 mmol) at room temperature under an argon atmosphere, and the mixture was placed in an ice bath. Thereafter, o-dichlorobenzene (0.50 ml) was added while stirring in an ice bath, followed by 2,6-di-tert-butylpyridine (0.178 g, 0.90 mmol). After completion of the dropwise addition, heating and stirring were performed at 90°C for 4 hours, at 120°C for 16 hours, at 150°C for 4 hours, and at 180°C for 4 hours. The reaction solution was cooled to room temperature, and hydrogen iodide in the reaction solution was distilled off under reduced pressure. After dichloromethane (20 ml) was added to dilute the reaction solution, phosphate buffer (pH=7, 30 ml) was added at room temperature, the aqueous layer was extracted three times with dichloromethane, and then the solvent was distilled off under reduced pressure. The obtained crude product was washed with acetonitrile and subjected to a silica gel short pass (eluent: dichloromethane) to obtain compound (1-2) (68.2 mg, yield 53%) as a red solid.

The structure of the obtained compound was confirmed by NMR measurement.
¹ H-NMR (500 MHz, CDCl ₃ ): δ = 0.92-0.98 (m, 18H), 1.00-1.05 (m, 18H), 1.26 (s, 18H), 1. 34-1.53 (m, 48H), 1.82-1.95 (m, 6H), 2.41 (s, 12H), 2.47 (s, 12H), 2.53 (s, 12H) , 2.73-2.89 (m, 8H), 2.98-3.07 (m, 4H), 5.40 (s, 2H), 5.45 (s, 1H), 6.88 (s , 4H), 6.93 (s, 2H), 7.08 (s, 4H), 7.13 (s, 4H), 7.18 (s, 2H), 7.29 (s, 2H), 7 .37 (s, 2H), 7.43 (d, 2H), 7.93 (s, 4H), 8.25 (s, 2H), 8.27 (s, 4H), 8.80 (d, 4H), 8.85 (s, 2H), 9.08 (d, 2H)

[Synthesis example (3): Synthesis of compound (1-3)]

In a test tube flask containing compound (I-3) (0.166 g, 0.05 mmol), 2,6-di-tert-butylpyridine (0.232 g, 1.2 mmol) was added at room temperature under a nitrogen atmosphere. o-Dichlorobenzene (0.50 ml) was added and stirred. Thereafter, the solution in the test tube flask was added to a Schlenk containing boron triiodide (0.784 g, 2.0 mmol) using a cannula. The test tube flask was washed twice with o-dichlorobenzene (0.50 ml) and added to Schlenk. Thereafter, heating and stirring were performed at 150° C. for 48 hours. The reaction solution was cooled to room temperature, and hydrogen iodide in the reaction solution was distilled off under reduced pressure. After diluting the reaction solution by adding dichloromethane (20 ml), phosphate buffer (pH=7, 30 ml) was added at room temperature, the aqueous layer was extracted three times with dichloromethane, and the solvent was distilled off under reduced pressure. The obtained crude product was washed with acetonitrile and hexane to obtain compound (1-3) (0.101 g, yield 60%) as a red solid.

The structure of the obtained compound was confirmed by NMR measurement.
^1H -NMR (500MHz, C ₂ D ₂ Cl ₄ ): δ = 0.94-1.09 (m, 48H), 1.27 (s, 18H), 1.36-1.51 (m, 64H) ), 1.94 (s, 8H), 2.36 (s, 12H), 2.49 (s, 12H), 2.54 (s, 12H), 2.55 (s, 12H), 2.80 -2.92 (m, 12H), 3.02-3.11 (m, 12H), 5.46 (s, 2H), 5.51 (s, 2H), 6.89 (s, 4H), 6.96 (s, 2H), 7.09 (s, 4H), 7.14 (s, 10H), 7.30 (s, 2H), 7.38 (s, 4H), 7.44 (d , 2H), 7.98 (s, 6H), 8.30 (s, 4H), 8.31 (s, 4H), 8.82 (s, 6H), 8.86 (s, 2H), 9 .05 (d, 2H)

[Synthesis example (4): Synthesis of compound (1-4)]

In a test tube flask containing compound (I-4) (0.167 g, 0.05 mmol), 2,6-di-tert-butylpyridine (0.232 g, 1.2 mmol) was added at room temperature under a nitrogen atmosphere. o-Dichlorobenzene (0.50 ml) was added and stirred. The solution in the test tube flask was then added to a Schlenk containing boron triiodide (0.627 g, 1.6 mmol) using a cannula. Furthermore, the test tube flask was washed twice with o-dichlorobenzene (0.50 ml) and added to Schlenk. Thereafter, the mixture was heated to 150°C and stirred for 24 hours. The reaction solution was cooled to room temperature, and hydrogen iodide in the reaction solution was distilled off under reduced pressure. After diluting the reaction solution by adding dichloromethane (20 ml), a phosphate buffer solution (pH=7, 20 ml) was added at room temperature, the aqueous layer was extracted three times with dichloromethane, and then the solvent was distilled off under reduced pressure. The obtained crude product was washed with acetonitrile, washed with hexane, and subjected to GPC (eluent: toluene) to obtain compound (1-4) (82.0 mg, yield 49%) as a yellow solid. Ta.

The structure of the obtained compound was confirmed by NMR measurement.
¹ H-NMR (500 MHz, C ₂ D ₂ Cl ₄ ): δ = 0.72-0.76 (t, 18H), 0.86-0.91 (m, 24H), 0.97 (t, 6H) ), 1.16 (s, 18H), 1.32-1.48 (m, 64H), 1.85-1.93 (s, 8H), 2.07 (s, 36H), 2.91 ( s, 12H), 2.96-3.04 (m, 4H), 3.20-3.40 (m, 12H), 5.34 (s, 4H), 6.03 (s, 2H), 6 .05 (s, 1H), 6.49 (s, 8H), 6.50 (s, 4H), 6.71 (s, 4H), 6.76 (s, 6H), 6.86 (s, 2H), 6.91 (s, 2H), 7.30 (d, 2H), 8.24 (s, 2H), 8.31 (s, 2H), 8.35 (s, 4H), 8. 77 (s, 2H), 8.96 (d, 2H), 9.15 (s, 4H), 9.16 (s, 2H), 10.7 (s, 2H), 10.7 (s, 1H) )

[Synthesis example (5): Synthesis of compound (1-5)]

Compound (I-5b) was synthesized from compound (I-5a) in the same manner as in Synthesis Example (1).
Tris(dibenzylideneacetone)dipalladium(0) (4.60 mg, 5.0 μmol), tri-tert-butylphosphonium tetrafluoroborate (4.2 mg, 20 μmol), compound (I-5b) (94.6 mg, Toluene (1.0 mL) was added to N-phenylnaphthalen-2-amine (26.3 mg, 0.12 mmol), and sodium-tert-butoxide (11.5 mg, 0.12 mmol) at room temperature under a nitrogen atmosphere. The mixture was heated and stirred at 80° C. for 16 hours. After the reaction solution was cooled to room temperature, it was filtered using a silica gel short pass column (eluent: dichloromethane), and the solvent was distilled off under reduced pressure to obtain a crude product. The obtained crude product was purified by silica gel column chromatography (eluent; hexane:toluene = 3:1, 7:3, 2:1 (volume ratio)) to obtain compound (1-5) (58 .6 mg, yield 52%) was obtained as a yellow solid.

The structure of the obtained compound was confirmed by NMR measurement.
¹ H-NMR (500 MHz, CDCl ₃ ): δ = 1.10 (s, 36H), 1.06 (s, 36H), 2.23 (s, 12H), 2.43 (s, 6H), 3 .18 (s, 6H), 5.78 (s, 2H), 5.84 (d, 2H), 6.15 (s, 1H), 6.80 (d, 4H), 6.83 (d, 4H), 6.94-6.98 (m, 8H), 7.07-7.15 (m, 14H), 7.28-7.35 (m, 6H), 7.49 (d, 2H) , 7.57 (d, 4H), 7.69 (d, 2H), 7.85 (d, 2H), 8.36 (s, 2H), 8.79 (s, 2H), 8.91 ( d, 2H), 9.51 (d, 2H), 11.1 (s, 1H)
¹³ C-NMR (126 MHz, CDCl ₃ ): δ = 20.7 (2C), 21.1 (2C), 21.3 (4C), 31.3 (12C), 31.7 (12C), 34. 7 (4C + 4C), 95.6 (2C), 104.9 (1C), 110.8 (2C), 111.3 (2C), 111.6 (2C), 116.5 (2C), 120.5 (2C), 120.6 (2C), 121.2 (2C), 121.3 (2C), 121.5 (2C), 122.0 (2C), 122.5 (2C), 123.3 ( 2C), 123.5 (2C), 124.0 (4C), 124.2 (4C), 124.6 (2C), 124.7 (2C), 124.8 (4C), 125.6 (2C ), 125.8 (2C), 126.1 (2C), 126.2 (2C), 127.0 (2C), 127.4 (2C), 128.2 (4C), 128.8 (2C) , 129.2 (4C), 130.3 (2C), 132.9 (2C), 133.3 (2C), 134.3 (2C), 135.6 (2C), 135.7 (2C), 136.8 (2C), 137.0 (4C), 137.3 (2C), 140.4 (2C), 140.8 (2C), 141.5 (2C), 141.8 (2C), 141 .9 (2C), 142.3 (2C), 144.0 (1C), 144.9 (2C), 147.2 (2C), 150.3 (2C), 150.6 (2C), 151. 3 (2C), 151.4 (2C), 152.2 (4C), 152.8 (4C), 152.9 (2C)
^11B -NMR (160MHz, _CDCl3 ): δ=37.9

[Synthesis example (6): Synthesis of compound (1-6)]

Under a nitrogen atmosphere, compound (I-6) (0.150 g, 0.075 mmol), boron triiodide (0.705 g, 1.80 mmol), 2,6-di-tert-butylpyridine (0.305 ml, 1 .36 mmol) and toluene (1.5 ml) were stirred at room temperature for 5 hours. Thereafter, a phosphate buffer solution (pH=6.8, 50 ml) was added to the reaction mixture at 0° C., and the aqueous layer was extracted three times with toluene, and then the solvent was distilled off under reduced pressure. Toluene (3.0 ml) and acetic acid (1.0 ml) were added to the obtained crude product, heated to 90° C., and stirred for 20 hours. After the reaction solution was cooled to room temperature, saturated aqueous sodium hydrogen carbonate solution (50 ml) was added at room temperature, the aqueous layer was extracted three times with toluene, and then the solvent was distilled off under reduced pressure. By purifying the residue with silica gel column chromatography (eluent; hexane:dichloromethane = 2:1 (volume ratio)), compound (1-6) (10.1 mg, 6.7% yield) was obtained as a yellow solid. Obtained.

The structure of the obtained compound was confirmed by NMR measurement.
¹ H-NMR (400 MHz, CDCl ₃ ): δ = 1.26 (s, 18H), 1.36 (s, 18H), 2.11 (s, 12H), 2.40 (s, 12H), 2 .43 (s, 12H), 5.52 (s, 2H), 6.23 (d, 2H), 6.59 (s, 1H), 6.80 (t, 2H), 6.90 (s, 4H), 6.94 (s, 2H), 6.96 (s, 4H), 6.97 (s, 2H), 7.07 (s, 2H), 7.10 (s, 4H), 7. 15 (s, 2H), 7.17 (s, 2H), 7.33 (d, 2H), 7.66 (d, 2H), 7.84 (t, 2H), 8.37 (d, 2H) ), 8.60 (d, 2H), 8.96 (d, 2H), 9.26 (d, 2H), 9.60 (d, 2H), 10.96 (s, 2H)

[Synthesis example (7): Synthesis of compound (1-7)]

Under a nitrogen atmosphere, compound (I-7) (0.220 g, 0.100 mmol), boron triiodide (0.638 g, 1.60 mmol), 2,6-di-tert-butylpyridine (0.270 ml, 1 .20 mmol) and 1,2-dichlorobenzene (2.0 ml) were stirred at room temperature for 21 hours. Thereafter, a phosphate buffer solution (pH=6.8, 50 ml) was added to the reaction mixture at 0° C., and the aqueous layer was extracted three times with dichloromethane, and then the solvent was distilled off under reduced pressure. The obtained crude product was purified by silica gel column chromatography (eluent: hexane: dichloromethane = 3:2 (volume ratio)) to obtain compound (1-7) (189.8 mg, 86% yield). ) was obtained as an orange solid.

The structure of the obtained compound was confirmed by NMR measurement.
¹ H-NMR (400 MHz, CDCl ₃ ): δ = 1.02 (s, 36H), 1.25 (s, 18H), 1.33 (s, 18H), 2.38 (s, 12H), 2 .39 (s, 12H), 5.47 (s, 2H), 6.86 (s, 4H), 6.90 (s, 4H), 6.92 (t, 4H), 7.04 (s, 2H), 7.11 (s, 2H), 7.13 (s, 2H), 7.14 (s, 2H), 7.30 (s, 2H), 7.37 (d, 2H), 7. 56-7.61 (m, 6H), 7.93 (s, 1H), 8.42 (s, 2H), 8.76 (s, 2H), 9.03 (d, 2H), 9.16 (s, 2H), 9.53 (d, 2H), 10.90 (s, 2H)
^13C -NMR (126MHz, CD ₂ Cl ₄ ): δ = 21.3 (8C), 22.7 (2C), 31.1 (18C), 31.2 (6C), 34.9 (4C), 35.1 (2C), 35.2 (2C), 94.8 (2C), 96.3 (1C), 110.3 (2C), 110.9 (2C), 112.2 (2C), 112 .4 (2C), 114.1 (2C), 114.4 (2C), 117.7 (2C), 117.9 (2C), 118.3 (2C), 121.6 (2C), 122. 1 (3C), 122.3 (2C), 123.1 (2C), 123.5 (2C), 123.8 (2C), 124.8 (6C), 125.0 (2C), 125.7 (2C), 126.4 (2C), 127.3 (8C), 129.3 (4C), 130.5 (2C), 132.4 (2C), 133.7 (2C), 134.7 ( 2C), 135.0 (2C), 140.1 (2C), 140.2 (8C), 140.7 (2C), 141.9 (4C), 142.1 (2C), 142.9 (2C ), 143.5 (2C), 145.7 (2C), 147.6 (2C), 147.8 (2C), 148.4 (2C), 150.9 (2C), 151.0 (2C) , 151.9 (8C), 153.8 (2C), 154.1 (2C)

[Synthesis example (8): Synthesis of compound (2-11)]

Into a test tube flask containing Compound (II-1) (0.157 g) were added 2,6-di-tert-butylpyridine (0.246 g) and o-dichlorobenzene (1.0 ml) at room temperature under a nitrogen atmosphere. ) was added and stirred. The solution in the test tube flask was then added to the Schlenk containing boron triiodide (0.625 g) using a cannula. Furthermore, the test tube flask was washed twice with o-dichlorobenzene (1.0 ml) and added to Schlenk. Thereafter, the mixture was heated to 120°C and stirred for 24 hours. The reaction solution was cooled to room temperature, and hydrogen iodide in the reaction solution was distilled off under reduced pressure. After diluting the reaction solution by adding dichloromethane (20 ml), a phosphate buffer solution (pH=7, 20 ml) was added at room temperature, the aqueous layer was extracted three times with dichloromethane, and then the solvent was distilled off under reduced pressure. The obtained crude product was washed with acetonitrile and subjected to silica gel column chromatography (eluent; hexane:toluene = 7:1 (volume ratio)) to obtain compound (2-11) (3.5 mg). was obtained as a yellow solid.

The structure of the obtained compound was confirmed by NMR measurement.
^1H -NMR (500MHz, C ₆ D ₆ ): δ = 0.59-0.70 (m, 48H), 0.99-1.10 (m, 64H), 1.25 (s, 12H), 1.54-1.59 (m, 8H), 1.68 (s, 12H), 1.71 (s, 12H), 2.55-2.66 (m, 6H), 2.72-2. 84 (s, 10H), 2.87 (s, 12H), 5.05 (s, 4H), 5.76 (s, 4H), 6.17 (s, 4H), 6.56 (s, 4H) ), 6.61 (s, 4H), 6.66 (s, 4H), 6.76 (s, 4H), 6.97 (s, 4H), 7.88 (s, 4H), 8.03 (s, 4H), 8.35 (s, 4H), 8.86 (d, 4H), 9.15-9.17 (m, 4H)
In addition, mass spectrometry was performed using a high-resolution mass spectrometer (HRMS).
HRMS (MALDI-TOF/MS) m/z [M] ⁺ calcd for C ₂₂₄ H ₂₃₆ B ₈ N ₁₂ 3182.970, observed 3182.972.

<Evaluation method of basic physical properties>
Evaluation of absorption and emission characteristics
The absorption spectrum of the sample was measured using an ultraviolet-visible-near-infrared spectrophotometer (Shimadzu Corporation, UV-2600). Further, the fluorescence spectrum or phosphorescence spectrum of the sample was measured using a spectrofluorophotometer (manufactured by Hitachi High-Tech Corporation, F-7000).

For measurement of fluorescence spectra, photoluminescence was measured at room temperature with excitation at an appropriate excitation wavelength. The phosphorescence spectrum was measured while the sample was immersed in liquid nitrogen (temperature 77 K) using an attached cooling unit. To observe the phosphorescence spectrum, an optical chopper was used to adjust the delay time from excitation light irradiation to the start of measurement. The samples were excited at the appropriate excitation wavelength and photoluminescence was measured.

Further, the fluorescence quantum yield (PLQY) was measured using an absolute PL quantum yield measuring device (manufactured by Hamamatsu Photonics Co., Ltd., C9920-02G).

Evaluation of fluorescence lifetime (delayed fluorescence) Fluorescence lifetime was measured at 300K using a fluorescence lifetime measuring device (manufactured by Hamamatsu Photonics Co., Ltd., C11367-01). Specifically, we observed an emission component with a fast fluorescence lifetime and an emission component with a slow fluorescence lifetime at the maximum emission wavelength measured at an appropriate excitation wavelength. When measuring the fluorescence lifetime of general organic EL materials that emit fluorescence at room temperature, a slow emission component involving a triplet component derived from phosphorescence is rarely observed due to the deactivation of the triplet component due to heat. do not have. If a slow emission component is observed in the compound to be evaluated, this indicates that triplet energy with a long excitation lifetime has been transferred to singlet energy due to thermal activation and observed as delayed fluorescence.

Calculation of energy gap (Eg) Calculated from the long wavelength end A (nm) of the absorption spectrum obtained by the method described above as Eg=1240/A.

Calculation of E(S, Sh), E(T, Sh), and ΔE(ST) The singlet excitation energy level E(S, Sh) is the tangent line passing through the inflection point on the shorter wavelength side of the peak of the fluorescence spectrum and the baseline. It was calculated from the wavelength B _Sh (nm) at the intersection with E (S, Sh) = 1240/B _Sh . Also, the triplet excitation energy level E(T, Sh) is calculated from the wavelength C _Sh (nm) at the intersection of the baseline and the tangent passing through the inflection point on the short wavelength side of the peak of the phosphorescence spectrum. )=1240/C _Sh .

ΔE(ST) is defined as the energy difference between E(S, Sh) and E(T, Sh), ΔE(ST)=E(S, Sh)−E(T, Sh). In addition, ΔE(ST) is, for example, "Purely organic electroluminescent material realizing 100% conversion from electricity to light", H. Kaji, H. Suzuki, T. Fukushima, K. Shizu, K. Katsuaki, S. Kubo,T It can also be calculated using the method described in Komino, H. Oiwa, F. Suzuki, A. Wakamiya, Y. Murata, C. Adachi, Nat. Commun. 2015, 6, 8476.

<Example A: Evaluation of basic physical properties>
The basic physical properties of the polycyclic aromatic compound synthesized in the synthesis example were evaluated.
[Example A1-1]
A solution of compound (1-1) dissolved in toluene at a concentration of 1×10 ⁻⁵ M was prepared, and its absorption characteristics and emission characteristics were measured. After removing dissolved oxygen by bubbling the solution with nitrogen, PLQY and fluorescence lifetime were measured.

[Examples A1-2 to A1-7, Example A2-1, Comparative Example A1-1]
In Example A1-1, evaluation was performed under the same conditions except that compound (1-1) was changed to the compound shown in Table 1. The results are summarized in Table 1.

The compound (Ref-1) used in Comparative Example A1-1 is the following compound.

<Example B: Evaluation of coating type organic EL element>
Next, an organic EL element obtained by coating and forming an organic layer will be described.

<Synthesis of polymeric host compound: SPH-101>
SPH-101 was synthesized according to the method described in International Publication No. 2015/008851. A copolymer in which M2 or M3 is bonded next to M1 is obtained, and it is estimated from the charging ratio that each unit is 50:26:24 (molar ratio).

<Synthesis of polymeric hole transport compound: XLP-101>
XLP-101 was synthesized according to the method described in JP-A-2018-61028. A copolymer in which M5 or M6 was bonded next to M4 was obtained, and it is estimated from the charging ratio that each unit was 40:10:50 (molar ratio).

<Examples C1 to C9>
A coating-type organic EL device is manufactured by preparing a coating solution of materials forming each layer.

<Production of organic EL devices of Examples C1 to C3>
Table 2 shows the material composition of each layer in the organic EL element.

The structure of "ET1" in Table 2 is shown below.

<Preparation of composition for forming light emitting layer (1)>
A luminescent layer forming composition (1) is prepared by stirring the following components until a uniform solution is obtained. By spin-coating the prepared luminescent layer-forming composition onto a glass substrate and heating and drying it under reduced pressure, a coated film with no film defects and excellent smoothness can be obtained.
SPH-101 1.96 weight%
Compound (X) 0.04% by weight
Xylene 69.00% by weight
Decalin 29.00% by weight

Compound (X) is a polycyclic aromatic compound represented by the above general formula (1) or general formula (2), or a monomer containing the polycyclic aromatic compound (that is, the monomer has a reactive substituent). A polymer compound that has been polymerized as a polymer, a polymer crosslinked product obtained by further crosslinking the polymer compound, a pendant type polymer compound in which the main chain type polymer is substituted with the monomer, or the pendant type polymer compound. It is a pendant type polymer crosslinked product that is further crosslinked. A polymer compound or a pendant polymer compound for obtaining a polymer crosslinked product or a pendant type polymer crosslinked product has a crosslinkable substituent.

<PEDOT:PSS solution>
A commercially available PEDOT:PSS solution (Clevios(TM) P VP AI4083, PEDOT:PSS aqueous dispersion, manufactured by Heraeus Holdings) is used.

<Preparation of OTPD solution>
OTPD (LT-N159, manufactured by Luminescence Technology Corp.) and IK-2 (photocationic polymerization initiator, manufactured by Sun-Apro Inc.) were dissolved in toluene, and the OTPD concentration was 0.7% by weight and the IK-2 concentration was 0.007% by weight. Prepare an OTPD solution of

<Preparation of XLP-101 solution>
XLP-101 is dissolved in xylene at a concentration of 0.6% by weight to prepare a 0.7% by weight XLP-101 solution.

<Preparation of PCz solution>
PCz (polyvinylcarbazole) is dissolved in dichlorobenzene to prepare a 0.7% by weight PCz solution.

<Example C1>
A PEDOT:PSS solution is spin-coated on a glass substrate on which ITO is deposited to a thickness of 150 nm, and then baked on a hot plate at 200°C for 1 hour to form a PEDOT:PSS film with a thickness of 40 nm. (hole injection layer). Next, the OTPD solution was spin-coated, dried on a hot plate at 80°C for 10 minutes, exposed to light using an exposure machine at an exposure intensity of 100 mJ/cm ² , and baked on a hot plate at 100°C for 1 hour to form the solution. An OTPD film with a thickness of 30 nm that is insoluble in is formed (hole transport layer). Next, the luminescent layer forming composition (1) is spin-coated and baked on a hot plate at 120° C. for 1 hour to form a luminescent layer with a thickness of 20 nm.

The prepared multilayer film was fixed to a substrate holder of a commercially available evaporation apparatus (manufactured by Showa Shinku Co., Ltd.), and a molybdenum evaporation boat containing ET1, a molybdenum evaporation boat containing LiF, and a tungsten evaporation boat containing aluminum were used. Attach the vapor deposition boat. After reducing the pressure in the vacuum chamber to 5×10 ⁻⁴ Pa, ET1 is heated and deposited to a thickness of 30 nm to form an electron transport layer. The deposition rate when forming the electron transport layer is 1 nm/sec. Thereafter, LiF is heated and deposited at a deposition rate of 0.01 to 0.1 nm/sec to a film thickness of 1 nm. Next, aluminum is heated and evaporated to a thickness of 100 nm to form a cathode. In this way, an organic EL element is obtained.

<Example C2>
An organic EL device is obtained in the same manner as in Example C1. Note that the hole transport layer is formed by spin coating an XLP-101 solution and baking it on a hot plate at 200° C. for 1 hour to form a film with a thickness of 30 nm.

<Example C3>
An organic EL device is obtained in the same manner as in Example C1. Note that the hole transport layer is formed by spin coating a PCz solution and baking it on a hot plate at 120° C. for 1 hour to form a film with a thickness of 30 nm.

<Production of organic EL devices of Examples C4 to C6>
Table 3 shows the material composition of each layer in the organic EL element.

<Preparation of light-emitting layer forming compositions (2) to (4)>
A composition for forming a light emitting layer (2) is prepared by stirring the following components until a uniform solution is obtained.
mCBP 1.98% by weight
Compound (X) 0.02% by weight
Toluene 98.00% by weight

A composition for forming a light emitting layer (3) is prepared by stirring the following components until a uniform solution is obtained.
SPH-101 1.98% by weight
Compound (X) 0.02% by weight
Xylene 98.00% by weight

A luminescent layer forming composition (4) is prepared by stirring the following components until a uniform solution is obtained.
DOBNA 1.98% by weight
Compound (X) 0.02% by weight
Toluene 98.00% by weight

In Table 3, "mCBP" is 3,3'-bis(N-carbazolyl)-1,1'-biphenyl, and "DOBNA" is 3,11-di-o-tolyl-5,9-dioxa- 13b-boranaphtho[3,2,1-de]anthracene, and "TSPO1" is diphenyl[4-(triphenylsilyl)phenyl]phosphine oxide. The chemical structure is shown below.

<Example C4>
After spin-coating ND-3202 (manufactured by Nissan Chemical Industries) solution on a glass substrate on which ITO was deposited to a thickness of 45 nm, it was heated at 50°C for 3 minutes in an air atmosphere, and then heated at 230°C for 15 minutes. By heating for a minute, an ND-3202 film with a thickness of 50 nm is formed (hole injection layer). Next, an XLP-101 solution is spin-coated and heated on a hot plate at 200° C. for 30 minutes in a nitrogen gas atmosphere to form an XLP-101 film with a thickness of 20 nm (hole transport layer). Next, the luminescent layer forming composition (2) is spin-coated and heated at 130° C. for 10 minutes in a nitrogen gas atmosphere to form a 20 nm luminescent layer.

The prepared multilayer film was fixed to a substrate holder of a commercially available evaporation apparatus (manufactured by Showa Shinku Co., Ltd.), and a molybdenum evaporation boat containing TSPO1, a molybdenum evaporation boat containing LiF, and a tungsten evaporation boat containing aluminum were used. Attach the vapor deposition boat. After reducing the pressure in the vacuum chamber to 5×10 ⁻⁴ Pa, TSPO1 is heated and deposited to a thickness of 30 nm to form an electron transport layer. The deposition rate when forming the electron transport layer is 1 nm/sec. Thereafter, LiF is heated and deposited at a deposition rate of 0.01 to 0.1 nm/sec to a film thickness of 1 nm. Next, aluminum is heated and evaporated to a thickness of 100 nm to form a cathode. In this way, an organic EL element is obtained.

<Example C5 and C6>
An organic EL device is obtained in the same manner as in Example C4 using the composition for forming a light emitting layer (3) or (4).

<Production of organic EL devices of Examples C7 to C9>
Table 4 shows the material composition of each layer in the organic EL element.

<Preparation of light-emitting layer forming compositions (5) to (7)>
A luminescent layer forming composition (5) is prepared by stirring the following components until a uniform solution is obtained.
mCBP 1.80% by weight
2PXZ-TAZ 0.18 weight%
Compound (X) 0.02% by weight
Toluene 98.00% by weight

A luminescent layer forming composition (6) is prepared by stirring the following components until a uniform solution is obtained.
SPH-101 1.80% by weight
2PXZ-TAZ 0.18 weight%
Compound (X) 0.02% by weight
Xylene 98.00% by weight

A luminescent layer forming composition (7) is prepared by stirring the following components until a uniform solution is obtained.
DOBNA 1.80% by weight
2PXZ-TAZ 0.18 weight%
Compound (X) 0.02% by weight
Toluene 98.00% by weight

In Table 4, "2PXZ-TAZ" is 10,10'-((4-phenyl-4H-1,2,4-triazole-3,5-diyl)bis(4,1-phenyl))bis(10H -phenoxazine). The chemical structure is shown below.

<Example C7>
After spin-coating ND-3202 (manufactured by Nissan Chemical Industries) solution on a glass substrate on which ITO was deposited to a thickness of 45 nm, it was heated at 50°C for 3 minutes in an air atmosphere, and then heated at 230°C for 15 minutes. By heating for a minute, an ND-3202 film with a thickness of 50 nm is formed (hole injection layer). Next, an XLP-101 solution is spin-coated and heated on a hot plate at 200° C. for 30 minutes in a nitrogen gas atmosphere to form an XLP-101 film with a thickness of 20 nm (hole transport layer). Next, the luminescent layer forming composition (5) is spin-coated and heated at 130° C. for 10 minutes in a nitrogen gas atmosphere to form a 20 nm luminescent layer.

The prepared multilayer film was fixed to a substrate holder of a commercially available evaporation apparatus (manufactured by Showa Shinku Co., Ltd.), and a molybdenum evaporation boat containing TSPO1, a molybdenum evaporation boat containing LiF, and a tungsten evaporation boat containing aluminum were used. Attach the vapor deposition boat. After reducing the pressure in the vacuum chamber to 5×10 ⁻⁴ Pa, TSPO1 is heated and deposited to a thickness of 30 nm to form an electron transport layer. The deposition rate when forming the electron transport layer is 1 nm/sec. Thereafter, LiF is heated and deposited at a deposition rate of 0.01 to 0.1 nm/sec to a film thickness of 1 nm. Next, aluminum is heated and evaporated to a thickness of 100 nm to form a cathode. In this way, an organic EL element is obtained.

<Example C8 and C9>
An organic EL device is obtained in the same manner as in Example C7 using the composition for forming a light emitting layer (6) or (7).

As mentioned above, some of the compounds according to the present invention have been evaluated as materials for organic EL devices, and have been shown to be excellent materials. However, other compounds that have not been evaluated have the same basic skeleton, and the overall It is a compound having a similar structure, and those skilled in the art can understand that it is a similarly excellent material for organic EL devices.

According to a preferred embodiment of the present invention, it is possible to provide a polycyclic aromatic compound having a novel structure that can be used as a material for organic devices such as a material for organic EL elements, and the polycyclic aromatic compound By using this, it is possible to provide an excellent organic device such as an organic EL element.

100 Organic electroluminescent device 101 Substrate 102 Anode 103 Hole injection layer 104 Hole transport layer 105 Light emitting layer 106 Electron transport layer 107 Electron injection layer 108 Cathode

Claims (40)

Polycyclic aromatic compound represented by the following general formula (1) or general formula (2):

In the above general formula (1) and general formula (2),
[φ]n is the following formula (φ-a-1) to (φ-a-6):

At least one unit structure selected from the group consisting of, and the following formula (φ-b):

The unit structure of
are configured by connecting n pieces in total, and in this case, the formulas (φ-a-1) to (φ-a-6) and the formula (φ-b) are alternately connected,
ⁿ is _an integer ^{of 3} _or more; can be,
The R ¹ is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl,
The R ² is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl,
In this case, two R ² may be bonded to each other to form a ring,
R ¹ or R ² may be bonded to at least one of ring a, ring b, ring d, and ring e through a linking group or a single bond to form a ring,
Y is each independently B, P, P=O, P=S, Al, Ga, As, Si-R ³ , or Ge-R ³ ,
The R ³ is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl,
Z is each independently -C(-R ⁴ )= or -N=, and in this case, any "-C(-R ⁴ )=C(-R ⁴ )-" is "-N (-R ⁴ )-", "-O-", "-S-", "-C(-R ⁴ ) _2- ", "-Si(-R ⁴ ) _2- ", or "-Se-" The two R ^4s in "-C(-R ⁴ ) ₂ --" and the two R ^4s in "-Si(-R ⁴ ) ₂ --" each independently represent Single bond, -CR ⁵ =CR ⁵ -, -C≡C-, -N(-R ⁵ )-, -O-, -S-, -C(-R ⁵ ) ₂ -, -Si(-R ⁵ ) ₂ -, may be bonded via -C(=O)- or -Se-,
The above R ⁴ is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino (two aryls are bonded to each other via a linking group or a single bond); ), substituted or unsubstituted diheteroarylamino (two heteroaryls may be bonded to each other via a linking group or a single bond), substituted or unsubstituted arylheteroarylamino (aryl and Heteroaryl may be bonded to each other via a linking group or a single bond), substituted or unsubstituted diarylboryl (two aryls may be bonded to each other via a single bond, a linking group, or a single bond) ), substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstituted amino,
The R ⁵ is each independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl,
In this case, two Z of different c rings, Z of the c ring and Z of the d ring, Z of the c ring and Z of the e ring may be bonded by a linking group or a single bond to form a ring,
At least one of the a-ring, b-ring, c-ring, d-ring, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl in the general formula (1) or general formula (2) has at least one It may be condensed with a cycloalkane, at least one hydrogen in the cycloalkane may be substituted, and at least one "-CH ₂ -" in the cycloalkane may be substituted with "-O-". Good too,
In the general formula (1) or general formula (2), at least one hydrogen may be replaced with cyano, halogen, or deuterium. X is >NR ¹ ,
Y is B,
The polycyclic aromatic compound according to claim 1, wherein Z is -C(-R ⁴ )=. The polycyclic aromatic compound according to claim 1, wherein [φ]n includes a unit structure of formula (φ-a-1) and a unit structure of formula (φ-b). The polycyclic aromatic according to claim 1, wherein [φ]n includes a unit structure of formulas (φ-a-1) to (φ-a-3) and a unit structure of formula (φ-b) Compound. The polycyclic aromatic compound according to claim 1, wherein n is 3 to 9. The polycyclic aromatic compound according to claim 1, wherein R ⁴ is each independently hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted carbazolyl, or substituted or unsubstituted diphenylamino. The polycyclic aromatic compound according to claim 1, wherein at least one of R ⁴ is alkyl having 8 to 30 carbon atoms. The polycyclic aromatic compound according to claim 1, wherein [φ]n includes a unit structure of the following formula (φ-1):

In the above formula (φ-1),
X is each independently >NR ¹ , >O, >C(-R ² ) ₂ , >Si(-R ² ) ₂ , >S, or >Se;
The R ¹ is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl,
The R ² is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl,
In this case, two R ² may be bonded to each other to form a ring,
R ¹ or R ² may be bonded to at least one of ring a, ring b, ring d, and ring e through a linking group or a single bond to form a ring,
Y is each independently B, P, P=O, P=S, Al, Ga, As, Si-R ³ , or Ge-R ³ ,
The R ³ is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl,
Z is each independently -C(-R ⁴ )= or -N=, and in this case, any "-C(-R ⁴ )=C(-R ⁴ )-" is "-N (-R ⁴ )-", "-O-", "-S-", "-C(-R ⁴ ) _2- ", "-Si(-R ⁴ ) _2- ", or "-Se-" The two R ^4s in "-C(-R ⁴ ) ₂ --" and the two R ^4s in "-Si(-R ⁴ ) ₂ --" each independently represent Single bond, -CR ⁵ =CR ⁵ -, -C≡C-, -N(-R ⁵ )-, -O-, -S-, -C(-R ⁵ ) ₂ -, -Si(-R ⁵ ) ₂ -, may be bonded via -C(=O)- or -Se-,
The above R ⁴ is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino (two aryls are bonded to each other via a linking group or a single bond); ), substituted or unsubstituted diheteroarylamino (two heteroaryls may be bonded to each other via a linking group or a single bond), substituted or unsubstituted arylheteroarylamino (aryl and Heteroaryl may be bonded to each other via a linking group or a single bond), substituted or unsubstituted diarylboryl (two aryls may be bonded to each other via a single bond, a linking group, or a single bond) ), substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstituted amino,
Each R ⁵ is independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl. [φ]n is the following formula (φ-1-1):

The polycyclic aromatic compound according to claim 8, comprising a unit structure of. [φ]n is the following formula (φ-1-2):

[In the above formula (φ-1-2),
R ⁶ is each independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino (even if two aryls are bonded to each other via a linking group or a single bond) substituted or unsubstituted diheteroarylamino (two heteroaryls may be bonded to each other via a linking group or a single bond), substituted or unsubstituted arylheteroarylamino (aryl and heteroaryl may be bonded to each other via a linking group or a single bond), substituted or unsubstituted diarylboryl (two aryls may be bonded to each other via a single bond or a linking group or a single bond), substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstituted amino,
R ⁷ is each independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl]
The polycyclic aromatic compound according to claim 9, comprising a unit structure of. The polycyclic aromatic compound according to claim 1, wherein [φ]n includes a unit structure of the following formula (φ-2):

In the above formula (φ-2),
X is each independently >NR ¹ , >O, >C(-R ² ) ₂ , >Si(-R ² ) ₂ , >S, or >Se;
The R ¹ is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl,
The R ² is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl,
In this case, two R ² may be bonded to each other to form a ring,
R ¹ or R ² may be bonded to at least one of ring a, ring b, ring d, and ring e through a linking group or a single bond to form a ring,
Y is each independently B, P, P=O, P=S, Al, Ga, As, Si-R ³ , or Ge-R ³ ,
The R ³ is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl,
Z is each independently -C(-R ⁴ )= or -N=, and in this case, any "-C(-R ⁴ )=C(-R ⁴ )-" is "-N (-R ⁴ )-", "-O-", "-S-", "-C(-R ⁴ ) _2- ", "-Si(-R ⁴ ) _2- ", or "-Se-" The two R ^4s in "-C(-R ⁴ ) ₂ --" and the two R ^4s in "-Si(-R ⁴ ) ₂ --" each independently represent Single bond, -CR ⁵ =CR ⁵ -, -C≡C-, -N(-R ⁵ )-, -O-, -S-, -C(-R ⁵ ) ₂ -, -Si(-R ⁵ ) ₂ -, may be bonded via -C(=O)- or -Se-,
The above R ⁴ is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino (two aryls are bonded to each other via a linking group or a single bond); ), substituted or unsubstituted diheteroarylamino (two heteroaryls may be bonded to each other via a linking group or a single bond), substituted or unsubstituted arylheteroarylamino (aryl and Heteroaryl may be bonded to each other via a linking group or a single bond), substituted or unsubstituted diarylboryl (two aryls may be bonded to each other via a single bond, a linking group, or a single bond) ), substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstituted amino,
Each R ⁵ is independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl. [φ]n is the following formula (φ-2-1):

The polycyclic aromatic compound according to claim 11, comprising a unit structure of. [φ]n is the following formula (φ-2-2):

[In the above formula (φ-2-2),
R ⁶ is each independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino (even if two aryls are bonded to each other via a linking group or a single bond) substituted or unsubstituted diheteroarylamino (two heteroaryls may be bonded to each other via a linking group or a single bond), substituted or unsubstituted arylheteroarylamino (aryl and heteroaryl may be bonded to each other via a linking group or a single bond), substituted or unsubstituted diarylboryl (two aryls may be bonded to each other via a single bond or a linking group or a single bond), substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstituted amino,
R ⁷ is each independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl]
The polycyclic aromatic compound according to claim 12, comprising a unit structure of. The polycyclic aromatic compound according to claim 1, wherein [φ]n includes a unit structure of the following formula (φ-3):

In the above formula (φ-3),
X is each independently >NR ¹ , >O, >C(-R ² ) ₂ , >Si(-R ² ) ₂ , >S, or >Se;
The R ¹ is hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl,
The R ² is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl,
In this case, two R ² may be bonded to each other to form a ring,
R ¹ or R ² may be bonded to at least one of ring a, ring b, ring d, and ring e through a linking group or a single bond to form a ring,
Y is each independently B, P, P=O, P=S, Al, Ga, As, Si-R ³ , or Ge-R ³ ,
The R ³ is substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl,
Z is each independently -C(-R ⁴ )= or -N=, and in this case, any "-C(-R ⁴ )=C(-R ⁴ )-" is "-N (-R ⁴ )-", "-O-", "-S-", "-C(-R ⁴ ) _2- ", "-Si(-R ⁴ ) _2- ", or "-Se-" The two R ^4s in "-C(-R ⁴ ) ₂ --" and the two R ^4s in "-Si(-R ⁴ ) ₂ --" each independently represent Single bond, -CR ⁵ =CR ⁵ -, -C≡C-, -N(-R ⁵ )-, -O-, -S-, -C(-R ⁵ ) ₂ -, -Si(-R ⁵ ) ₂ -, may be bonded via -C(=O)- or -Se-,
The above R ⁴ is each independently hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino (two aryls are bonded to each other via a linking group or a single bond); ), substituted or unsubstituted diheteroarylamino (two heteroaryls may be bonded to each other via a linking group or a single bond), substituted or unsubstituted arylheteroarylamino (aryl and Heteroaryl may be bonded to each other via a linking group or a single bond), substituted or unsubstituted diarylboryl (two aryls may be bonded to each other via a single bond, a linking group, or a single bond) ), substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstituted amino,
Each R ⁵ is independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl. [φ]n is the following formula (φ-3-1):

The polycyclic aromatic compound according to claim 14, comprising a unit structure of. [φ]n is the following formula (φ-3-2):

[In the above formula (φ-3-2),
R ⁶ is each independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted diarylamino (even if two aryls are bonded to each other via a linking group or a single bond) substituted or unsubstituted diheteroarylamino (two heteroaryls may be bonded to each other via a linking group or a single bond), substituted or unsubstituted arylheteroarylamino (aryl and heteroaryl may be bonded to each other via a linking group or a single bond), substituted or unsubstituted diarylboryl (two aryls may be bonded to each other via a single bond or a linking group or a single bond), substituted or unsubstituted alkyl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or substituted or unsubstituted amino,
R ⁷ is each independently substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl]
The polycyclic aromatic compound according to claim 15, comprising a unit structure of. The polycyclic aromatic compound according to claim 1, selected from the group consisting of the following formulas (1-1) to (1-7) and formula (2-11):

In the formula, Me is methyl and tBu is butyl. A reactive compound obtained by substituting the polycyclic aromatic compound according to any one of claims 1 to 17 with a reactive substituent. A polymer compound obtained by polymerizing the reactive compound according to claim 18 as a monomer, or a polymer crosslinked product obtained by further crosslinking the polymer compound. A pendant polymer compound in which the main chain polymer is substituted with the reactive compound according to claim 18, or a pendant crosslinked polymer compound in which the pendant polymer compound is further crosslinked. A material for an organic device, comprising the polycyclic aromatic compound according to any one of claims 1 to 17. An organic device material containing the reactive compound according to claim 18. An organic device material comprising the polymer compound or crosslinked polymer according to claim 19. An organic device material containing the pendant polymer compound or pendant polymer crosslinker according to claim 20. The organic device material according to claim 21, wherein the organic device material is an organic electroluminescent element material, an organic field effect transistor material, an organic thin film solar cell material, or a wavelength conversion filter material. The material for an organic device according to claim 25, wherein the material for an organic electroluminescent element is a material for a light emitting layer. An ink composition comprising the polycyclic aromatic compound according to any one of claims 1 to 17 and an organic solvent. An ink composition comprising the reactive compound according to claim 18 and an organic solvent. An ink composition comprising a main chain polymer, the reactive compound according to claim 18, and an organic solvent. An ink composition comprising the polymer compound or crosslinked polymer according to claim 19 and an organic solvent. An ink composition comprising the pendant polymer compound or pendant polymer crosslinked product according to claim 20 and an organic solvent. An organic electroluminescent device comprising a pair of electrodes consisting of an anode and a cathode, and an organic layer disposed between the pair of electrodes and containing the polycyclic aromatic compound according to any one of claims 1 to 17. . 33. The organic electroluminescent device according to claim 32, wherein the organic layer is a light emitting layer. 33. The light-emitting layer includes a host and the polycyclic aromatic compound, a reactive compound, a polymer compound, a polymer crosslinker, a pendant polymer compound, or a pendant polymer crosslinker as a dopant. An organic electroluminescent device described in . 35. The organic electroluminescent device according to claim 34, wherein the host is an anthracene compound, a fluorene compound, or a dibenzochrycene compound. It has at least one layer of an electron transport layer and an electron injection layer disposed between the cathode and the light emitting layer, and at least one of the electron transport layer and the electron injection layer is made of a borane derivative, a pyridine derivative, or a fluoranthene derivative. Derivatives, BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, quinolinol metal complexes, thiazole derivatives, benzothiazole derivatives, silole derivatives and azoline derivatives The organic electroluminescent device according to claim 33, comprising at least one selected from the group consisting of: At least one of the electron transport layer and the electron injection layer further comprises an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal oxide, an alkali metal halide, an alkaline earth metal oxide, an alkaline earth Contains at least one selected from the group consisting of halides of similar metals, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals. , the organic electroluminescent device according to claim 36. or , a polymer crosslinked product obtained by further crosslinking the polymer compound, a pendant polymer compound obtained by reacting a low molecular compound capable of forming each layer with a main chain polymer, or a pendant polymer compound obtained by further crosslinking the polymer compound. 33. The organic electroluminescent device according to claim 32, further comprising a crosslinked pendant polymer crosslinked body. A display device or a lighting device comprising the organic electroluminescent element according to claim 32. A wavelength conversion filter comprising the wavelength conversion filter material according to claim 25.

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