WO2012133652A1

WO2012133652A1 - Charge transport material, organic electroluminescent element, and illumination device, display device, or light-emitting device characterized by using said element

Info

Publication number: WO2012133652A1
Application number: PCT/JP2012/058359
Authority: WO
Inventors: 北村　哲
Original assignee: 富士フイルム株式会社
Priority date: 2011-03-31
Filing date: 2012-03-29
Publication date: 2012-10-04
Also published as: KR20140020935A; JP2012216819A; KR101964477B1; JP5872944B2

Abstract

This charge transport material, which comprises a compound represented by the formula, has a high efficiency after storage at a high temperature, and has a high highest attained brightness (R¹⁰¹ and R¹⁰² each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, or a silyl group, and furthermore may be substituted by these groups or an amino group; a condensed ring aryl structure or a condensed ring heteroaryl structure are not contained in R¹⁰¹ or R¹⁰²; there is a total of at least five single-ring aromatic rings (the aromatic rings being six-membered rings of which the members are configured from carbon atoms or nitrogen atoms) in R¹⁰¹ and R¹⁰²; n₁₀₁is an integer from 0 to 11; n₁₀₂ is an integer from 0-9; the plurality of R¹⁰¹ and R¹⁰² may be the same or different; and A^A1-A^A9 each independently represent CH (the hydrogen atom of CH being optionally substituted with R¹⁰²) or a nitrogen atom).

Description

Charge transport material, organic electroluminescent element, and light emitting device, display device or illumination device using the element

The present invention relates to a charge transport material, an organic electroluminescent element, and a light emitting device, a display device, or a lighting device using the element.

Organic electroluminescent elements (hereinafter also referred to as “elements” and “organic EL elements”) are actively researched and developed because they can emit light with high luminance when driven at a low voltage. An organic electroluminescent element has an organic layer between a pair of electrodes, and electrons injected from the cathode and holes injected from the anode recombine in the organic layer, and the generated exciton energy is used for light emission. To do.

In recent years, the use of phosphorescent materials such as iridium (Ir) complexes and platinum (Pt) complexes has increased the efficiency of devices. In addition, a doped element using a light emitting layer in which a light emitting material is doped in a host material is widely used.
Development of the charge transport material contained in the host material used for a light emitting layer and other organic layers is also performed actively.
For example, Patent Document 1 discloses an organic electroluminescent device using a compound having a triphenylene structure, and uses a compound in which phenylene having a substituent (non-condensed aryl or heteroaryl) is bonded to the meta position. An organic electroluminescent device is described.

On the other hand, in recent years, various display devices such as an organic electroluminescent element have been widely used, and are required to operate stably for a long time under various environments. For example, in an in-vehicle use for an automobile, the interior of the vehicle is considerably hot during daytime driving or parking, so that it is also required that the characteristics do not change even after high-temperature storage. In addition, it is important that the organic electroluminescent element does not change its characteristics after being stored at such a high temperature from the viewpoint that it generates heat when driven to the same degree or more as a conventional light emitting device.

Special table 2010-535806 gazette

On the other hand, as a result of examining the characteristics of the organic electroluminescence device using the compound described in Patent Document 1, the inventors have found that the efficiency after high-temperature storage is low, and the heat resistance is insufficient. In addition to this, a new problem has been found that the maximum reached brightness is low.

The problem to be solved by the present invention is to provide a charge transport material and an organic electroluminescence device having high efficiency after storage at high temperature and high maximum attained luminance.

As a result of intensive studies by the present inventors, a compound containing a triphenylene structure and a monocyclic aromatic ring structure is linked in a specific linking manner to the compound specifically described in Patent Document 1, and the compound It has been found that by increasing the number of monocyclic aromatic rings in the inside, a charge transport material and an organic electroluminescence device having high efficiency after high-temperature storage and high maximum brightness can be provided.

That is, the present invention can be achieved by the following means.

[1] A charge transport material comprising a compound represented by the following general formula (1).

(In the general formula (1), R ¹⁰¹ and R ¹⁰² each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group, and may be further substituted with these groups or amino groups. However, the aromatic ring (aromatic ring monocyclic included in the .R ¹⁰¹ and R ¹⁰² which condensed aryl structure and condensed heteroaryl structure in R ¹⁰¹ and R ¹⁰² are not included, ring members carbon (Six or six-membered ring composed of atoms or nitrogen atoms) The total number is 5 or more, n ₁₀₁ represents an integer of 0 to 11, n ₁₀₂ represents an integer of 0 to 9, and a plurality of R ¹⁰¹ and R ¹⁰² are the same A ^A1 to A ^A9 each independently represent CH (the hydrogen atom of CH may be substituted with R ¹⁰² ) or a nitrogen atom.)
[2] The charge transport material according to [1], wherein the compound represented by the general formula (1) is represented by the following general formula (2).

In (formula (2), each R ¹¹¹ independently represent an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, or a silyl group, better .R ²³¹ ~ be substituted with these groups or amino groups R ²³⁴ independently represents an alkyl group, a fluorine atom, a silyl group or an amino group, R ²³⁵ to R ²³⁸ each independently represents an aryl group or a heteroaryl group, provided that R ¹¹¹ and R ²³¹ to R ²³⁸ are Does not include a condensed ring aryl structure or a condensed ring heteroaryl structure, and R ¹¹¹ and R ²³¹ to R ²³⁸ include a monocyclic aromatic ring (the aromatic ring is composed of a carbon atom or a nitrogen atom) A total of 3 to 6. n ₁₁₁ represents an integer of 0 to 11, y31 to y33 and y35 to y37 each independently represents an integer of 0 to 4, and y34 and y38 are Represents an integer of 0 to 5. A plurality of R ¹¹¹ and R ²³¹ to R ²³⁸ may be the same or different.A ^B1 to A ^B17 are each independently CH (the hydrogen atom of CH is substituted by R ²³¹ to R ²³⁸⁾ Or a ring member representing a nitrogen atom and constituting a 6-membered aromatic ring.)
[3] The charge transport according to [2], wherein A ^B3 in the general formula (2) represents CH, and a hydrogen atom of A ^B3 is substituted by at least one of R ^235. material.
[4] The charge transport material according to any one of [1] to [3], wherein n ₁₀₁ in the general formula (1) is 0.
[5] R ¹⁰¹ or R ¹⁰² in the general formula (1) represents a fluorine atom, a fluoroalkyl group, a cycloalkyl group, a silyl group, an alkylsilyl group, an arylsilyl group, a cycloalkylene group, or a silicon atom linking group. The charge transport material according to any one of [1] to [4], wherein the charge transport material is a substituent.
[6] As described in any one of [1] to [5], all the monocyclic aromatic rings included in the general formula (1) are 6-membered rings of a carbon atom skeleton. Charge transport material.
[7] The charge transport material according to any one of [1] to [6], wherein the compound represented by the general formula (1) is composed of only a carbon atom and a hydrogen atom.
[8] The charge transport material according to any one of [1] to [7], wherein the compound represented by the general formula (1) has a molecular weight of 1200 or less.
[9] The compound represented by the general formula (1) is a monocyclic aromatic ring (the aromatic ring is a six-membered ring composed of a carbon atom or a nitrogen atom) via a single bond. The number of the monocyclic aromatic rings continuously connected at the para position in the partial structure is 3 or less. The charge transport material according to any one of [1] to [8], wherein
[10] A substrate, a pair of electrodes disposed on the substrate and including an anode and a cathode, and an organic layer disposed between the electrodes, wherein the organic layer includes a phosphorescent material and [1] to [1] [9] An organic electroluminescent device comprising the charge transport material according to any one of [9].
[11] The organic electroluminescent element as described in [10], wherein the phosphorescent material is represented by the following general formula (E-1).

In (Formula (E-1), x1 and Z ² are each independently, .A ₁ representing a carbon atom or a nitrogen atom represents an atomic group forming a heterocycle of 5 or 6 membered with Z ¹ and the nitrogen atom B ₁ represents an atomic group that forms a 5- or 6-membered ring with Z ² and a carbon atom, (XY) represents a monoanionic bidentate ligand, and n _E1 represents an integer of 1 to 3. To express.)
[12] The organic electroluminescent element as described in [10] or [11], wherein the phosphorescent material represented by the general formula (E-1) is represented by the following general formula (E-2) .

(In the formula (E-2), are each A ^E1 ~ A ^E8 independently nitrogen atom or,, .R ^E representing a carbon atom substituted with R ^E represents a hydrogen atom or a substituent. (X- Y) represents a monoanionic bidentate ligand, and n _E2 represents an integer of 1 to 3.)
[13] The organic electric field according to any one of [10] to [12], wherein the phosphorescent material represented by the general formula (E-1) has a maximum emission wavelength of 500 nm to 700 nm. Light emitting element.
[14] The organic layer includes a light-emitting layer containing the phosphorescent material and another organic layer, and the light-emitting layer contains a compound represented by the general formula (1) [10] ] The organic electroluminescent element according to any one of [13] to [13].
[15] The organic layer includes a light-emitting layer containing the phosphorescent material and another organic layer, and the other organic layer includes a hole block layer disposed between the light-emitting layer and the cathode. The organic electroluminescent device according to any one of [10] to [14], wherein the hole blocking layer contains a compound represented by the general formula (1).
[16] The organic electroluminescence device as described in any one of [10] to [15], wherein the maximum emission wavelength is 500 nm to 550 nm.
[17] A light-emitting device, display device, or illumination device comprising the organic electroluminescent element according to any one of [10] to [16].
[18] A compound represented by the following general formula (1).

(In the general formula (1), R ¹⁰¹ and R ¹⁰² each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group, and may be further substituted with these groups or amino groups. However, the aromatic ring (aromatic ring monocyclic into .R ¹⁰¹ and R ¹⁰² which condensed aryl structure and condensed heteroaryl structure in R ¹⁰¹ and R ¹⁰² are not included, ring member carbon atoms or A total of 5 or more), n ₁₀₁ represents an integer of 0 to 11, n ₁₀₂ represents an integer of 0 to 9, and a plurality of R ¹⁰¹ and R ¹⁰² are the same A ^A1 to A ^A9 each independently represent CH (the hydrogen atom of CH may be substituted with R ¹⁰² ) or a nitrogen atom.)

By using the compound represented by the general formula (1) in the present invention, it is possible to provide a charge transport material and an organic electroluminescence device having high efficiency after high-temperature storage and high maximum brightness.

It is the schematic which shows an example of a structure of the organic electroluminescent element which concerns on this invention. It is the schematic which shows an example of the light-emitting device which concerns on this invention. It is the schematic which shows an example of the illuminating device which concerns on this invention.

Hereinafter, the contents of the present invention will be described in detail. The description of the constituent elements described below may be made based on typical embodiments of the present invention, but the present invention is not limited to such embodiments. In the present specification, “to” is used to mean that the numerical values described before and after it are included as a lower limit value and an upper limit value.

[Charge transport material]
The charge transport material of the present invention is characterized by comprising a compound represented by the following general formula (1).

(In the general formula (1), R ¹⁰¹ and R ¹⁰² each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group, and may be further substituted with these groups or amino groups. However, the aromatic ring (aromatic ring monocyclic into .R ¹⁰¹ and R ¹⁰² which condensed aryl structure and condensed heteroaryl structure in R ¹⁰¹ and R ¹⁰² are not included, ring member carbon atoms or A total of 5 or more), n ₁₀₁ represents an integer of 0 to 11, n ₁₀₂ represents an integer of 0 to 9, and a plurality of R ¹⁰¹ and R ¹⁰² are the same A ^A1 to A ^A9 each independently represent CH (the hydrogen atom of CH may be substituted with R ¹⁰² ) or a nitrogen atom.)
Although the charge transport material of the present invention has such a configuration, it is not bound by any theory, but the glass transition temperature Tg can be increased without impairing efficiency and driving durability, and further, a molecular excited state, Excited state and charge spread to a wide range of π-conjugated systems in the molecule when in the radical cation state or radical anion state. However, it can be driven stably. Therefore, the organic electroluminescent element using the charge transporting material of the present invention is excellent in efficiency after high temperature storage and maximum reached luminance.

The charge transport material of the present invention represented by the general formula (1) is preferably used for organic electronic elements such as electrophotography, organic transistors, organic photoelectric conversion elements (energy conversion applications, sensor applications, etc.), organic electroluminescence elements and the like. It is particularly preferable to use it for an organic electroluminescent device.

The charge transport material of the present invention can also be used for a thin film containing the compound represented by the general formula (1). The thin film can be formed using the composition by a dry film forming method such as an evaporation method or a sputtering method, or a wet film forming method such as a transfer method or a printing method. The thickness of the thin film may be any thickness depending on the application, but is preferably 0.1 nm to 1 mm, more preferably 0.5 nm to 1 μm, still more preferably 1 nm to 200 nm, and particularly preferably 1 nm to 100 nm. is there.

Hereinafter, the preferable range of the charge transport material comprising the compound represented by the general formula (1) will be described.
In the present invention, the hydrogen atom (H) in the description of the general formula (1) includes an isotope (deuterium atom, D), and the atoms constituting the substituent further include the isotope. Represents that.
In the present invention, when referred to as “substituent”, the substituent may be substituted. For example, the term “alkyl group” in the present invention includes an alkyl group substituted with a fluorine atom (for example, trifluoromethyl group) and an alkyl group substituted with an aryl group (for example, triphenylmethyl group). When the term “alkyl group having 1 to 6 carbon atoms” is used, it means that all groups including substituted ones have 1 to 6 carbon atoms.
In the present invention, a substituent containing a fluorine atom, a fluoroalkyl group, a cycloalkyl group, a silyl group, an alkylsilyl group, an arylsilyl group, a cycloalkylene group or a silicon atom linking group is also referred to as a “specific substituent”. A silyl group substituted with an alkyl group and an aryl group is also included in the specific substituent.
However, in this specification, the “cycloalkylene group” means a generic name such as 1,4-cyclohexanediyl, 1,3-cyclohexanediyl, 1,2-cyclohexanediyl, cyclopentane, etc. It does not mean a ring with one atom removed.

<R ¹⁰¹ and R ^{102 in} general formula (1)>
In the general formula (1), R ¹⁰¹ and R ¹⁰² each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group, and may be further substituted with these groups or amino groups. However, R ¹⁰¹ and R ¹⁰² do not include a condensed ring aryl structure or a condensed ring heteroaryl structure. R ¹⁰¹ and R ¹⁰² contain a total of 5 or more monocyclic aromatic rings (the aromatic ring is a 6-membered ring composed of a carbon atom or a nitrogen atom). In the general formula (1), the ring member of the monocyclic aromatic ring (the aromatic ring is a six-membered ring composed of a carbon atom or a nitrogen atom) is the monocyclic aromatic ring. In the ring, the number of nitrogen atoms is preferably 3 or less, more preferably 2 or less, particularly preferably 1 or less, and particularly preferably 0.
In the general formula (1), R ¹⁰¹ and R ¹⁰² include a total of 5 monocyclic aromatic rings (the aromatic ring is a 6-membered ring composed of a carbon atom or a nitrogen atom). By including the above, the effects of the present invention can be achieved. The number of monocyclic aromatic rings contained in R ¹⁰¹ and R ¹⁰² is preferably 5 to 8 from the viewpoint of appropriate deposition, more preferably 5 to 7, and 5 to 6 It is particularly preferred.

When R ¹⁰¹ and R ¹⁰² are alkyl groups, the alkyl groups may be linear, branched or cyclic, and generally have 1 to 30 carbon atoms, preferably 1 to 20 carbon atoms. More preferably, it is an alkyl group having 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms, and most preferably 1 to 4 carbon atoms. For example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, t-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group, n -Octyl group, n-decyl group, n-hexadecyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, etc., including methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, t-butyl group Group, cyclopentyl group and cyclohexyl group are preferred, more preferably methyl group, ethyl group, n-propyl group, t-butyl group and cyclohexyl group, particularly preferably methyl group, isopropyl group and t-butyl group. And more preferably a methyl group or a t-butyl group.

The alkyl group as R ¹⁰¹ and R ¹⁰² may further have an alkyl group, aryl group, heteroaryl group, fluorine atom or silyl group as a substituent. Among them, the aryl group, heteroaryl group or fluorine atom is preferable.
When the alkyl group as R ¹⁰¹ and R ¹⁰² is substituted with a fluorine atom, it is more preferable that all hydrogen atoms are substituted with a fluorine atom to form a perfluoroalkyl group, and —CF ₂ CF ₂ CF ₃ It is particularly preferable to form a group or a trifluoromethyl group, and it is more preferable to form a trifluoromethyl group.
On the other hand, when the alkyl group as R ¹⁰¹ and R ¹⁰² is substituted with an aryl group or a heteroaryl group, the aryl group or heteroaryl group is a monocyclic aromatic ring (the aromatic ring is a member having a carbon atom Or a 6-membered ring composed of nitrogen atoms). In this case, the alkyl group as R ¹⁰¹ and R ¹⁰² is substituted with a plurality of monocyclic aromatic rings (the aromatic ring is a 6-membered ring composed of a carbon atom or a nitrogen atom). It is preferable.
When the alkyl group as R ¹⁰¹ and R ¹⁰² is further substituted with an alkyl group, the alkyl group as the further substituent is preferably a methyl group.
The alkyl group as R ¹⁰¹ and R ¹⁰² is more preferably substituted so as to be a quaternary carbon.

When R ¹⁰¹ and R ¹⁰² are silyl groups, the silyl group is preferably substituted, and the substituent is preferably an alkyl group or an aryl group. When the silyl group as R ¹⁰¹ and R ¹⁰² is substituted with an alkyl group or an aryl group, all hydrogen atoms are substituted with an alkyl group or an aryl group to form a trialkylsilyl group or a triarylsilyl group. Is more preferable, and it is particularly preferable to form a trimethylsilyl group or a triphenylsilyl group. The triarylsilyl group may be further substituted on the aryl group portion. In that case, the triarylsilyl group is preferably substituted with an aryl group, and more preferably substituted with a phenyl group.

When R ¹⁰¹ and R ¹⁰² are heteroaryl groups, the heteroaryl group is preferably a 5- or 6-membered heterocycle containing a nitrogen atom. Examples of the 5- or 6-membered heterocycle containing a nitrogen atom include a pyridine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, an imidazole ring, a pyrazole ring, an oxazole ring, a thiazole ring, a triazole ring, an oxadiazole ring, and a thiadiazole ring. Is mentioned. When the charge transport material of the present invention is used in an organic electroluminescent device, it may be a pyridine ring, a pyrazine ring, an imidazole ring, or a pyrazole ring from the viewpoints of complex stability, emission wavelength control, and emission quantum yield. More preferred are pyridine ring, imidazole ring and pyrazine ring, still more preferred are pyridine ring or imidazole ring, and most preferred is pyridine ring. However, R ¹⁰¹ and R ¹⁰² are preferably aryl groups rather than heteroaryl groups.

When R ¹⁰¹ and R ¹⁰² are an aryl group, it preferably has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, and examples thereof include phenyl, naphthyl, anthryl and the like. It is done. R ¹⁰¹ and R ¹⁰² are preferably a monocyclic aryl group, and more preferably a phenyl group.

The aryl group or heteroaryl group as R ¹⁰¹ and R ¹⁰² may further have an alkyl group, aryl group, heteroaryl group, fluorine atom, silyl group or amino group as a substituent.
When the aryl group or heteroaryl group as R ¹⁰¹ and R ¹⁰² is substituted with an alkyl group, a fluorine atom or a silyl group, the preferred range of the alkyl group, heteroaryl group, fluorine atom or silyl group as the substituent is , R ¹⁰¹ and R ¹⁰² are the same as when an alkyl group, a heteroaryl group, a fluorine atom or a silyl group. When the aryl group or heteroaryl group as R ¹⁰¹ and R ¹⁰² is substituted with an alkyl group, heteroaryl group, fluorine atom or silyl group, the number of these substituents is the aryl group as R ¹⁰¹ and R ¹⁰² or It is preferably 1 to 3 with respect to the heteroaryl group, more preferably 1 or 2, and particularly preferably 1.
When the aryl group or heteroaryl group as R ¹⁰¹ and R ¹⁰² is substituted with an amino group, the amino group is preferably further substituted with an alkyl group, an aryl group or a heteroaryl group. Is more preferably a tertiary amine. In this case, the preferred range of the alkyl group, aryl group or heteroaryl group which further substitutes the amino group is the same as the preferred range of the alkyl group, aryl group or heteroaryl group as R ¹⁰¹ and R ¹⁰² described above. .
When the aryl group or heteroaryl group is substituted with respect to the aryl group or heteroaryl group as R ¹⁰¹ and R ¹⁰² , the aryl group and arylene group, or the heteroaryl group and heteroarylene group formed by the substitution are These are preferably monocyclic, more preferably 6-membered monocyclic.

With respect to the aryl group or heteroaryl group as R ¹⁰¹ and R ¹⁰² , an aryl group or heteroaryl group is substituted to form a 6-membered monocyclic aryl group and arylene group, or heteroaryl group and heteroaryl group. When an arylene group, or these linking groups and substituents are connected in combination with each other, a monovalent substituent in which a single ring of these 6-membered rings is connected by a single bond (6-membered connected by a single bond). The number of monocyclic rings is preferably 2 to 6, more preferably 2 to 5, and particularly preferably 2 to 4. For example, preferred structures in the case where an aryl group and an arylene group which are 6-membered monocycles form a linking substituent include a biphenyl group, a terphenyl group, a quarterphenyl group and a kinkphenyl group.
The monovalent substituent in which a plurality of 6-membered monocycles are linked by a single bond is a monocyclic aromatic ring (the aromatic ring is a 6-membered ring composed of carbon atoms or nitrogen atoms) Have at least one partial structure in which 4 or more are bonded continuously through a single bond, and the number of the monocyclic aromatic rings connected continuously at the para position in the partial structure is The number is preferably 3 or less. That is, it is preferable that the monovalent substituent in which a plurality of 6-membered monocycles are linked by a single bond does not contain more than 3 para-substituted phenyl rings.
Among these, the monovalent substituent in which a plurality of 6-membered monocycles are linked by a single bond is preferably a phenyl group, a biphenyl group, a terphenyl group (particularly a p-terphenyl group or 3,5-diphenylphenyl). , A p-terphenyl group is more preferred), either a biphenyl group or a terphenyl group is more preferred, and a biphenyl group is most preferred. The above example has the same structure when a heteroaryl group and a heteroarylene group are linked.

When R ¹⁰¹ is an aryl group or a heteroaryl group, R ¹⁰¹ is particularly preferably represented by the following general formula (3).

(In the above formula, A ^A11 to A ^A33 each independently represents CH or a nitrogen atom, and are ring members constituting a 6-membered aromatic ring. R ²⁰¹ to R ²⁰⁴ each independently represents an alkyl group, a fluorine atom or a silyl group, y1 ~ y3 are each independently an integer of 0 ~ 4, y4 each independently .R ²⁰⁵ ~ R ²⁰⁸ represents an integer of 0 to 5 represents an aryl group or a heteroaryl group, y5 ~ y8 independently represents an integer of 0 to 2, provided that the sum of y1 and y5, the sum of y2 and y6, and the sum of y3 and y7 is 4 at the maximum, and the sum of y4 and y8 is 5 at the maximum. X1, x2 and x3 each independently represents 0 or 1, and x1 ≦ x2 ≦ x3.

In the general formula (3), the preferred range of R ²⁰¹ to R ^{204 is the same as} the preferred range of the alkyl group, fluorine atom or silyl group as R ¹⁰¹ and R ¹⁰² in the general formula (1). Among these, R ²⁰¹ to R ²⁰⁴ are preferably an alkyl group or a fluorine atom, and more preferably a methyl group, an n-propyl group, or a fluorine atom.
In the general formula (3), the preferred range of R ²⁰⁵ to R ^{208 is the same as} the preferred range of the aryl group or heteroaryl group as R ¹⁰¹ and R ¹⁰² in the general formula (1). Among these, R ²⁰⁵ to R ²⁰⁸ are preferably aryl groups, and more preferably phenyl groups.

In the general formula (3), the sum of y5 to y8, that is, the number of branches of the 6-membered aromatic ring in R ¹⁰¹ is preferably 0 or 1, particularly preferably 0.

In the general formula (3), when x1 to x3 are 1, y1 to y3 are preferably 0, y4 is preferably 0 to 2, and y5 to y8 are preferably 0. At this time, R ²⁰¹ is preferably an alkyl group, preferably an alkyl group having 1 to 3 carbon atoms, and more preferably a methyl group or an n-propyl group.
In the general formula (3), when x1 is 0 and x2 and x3 are 1, y1 is preferably 0 to 2, and y2 to y8 are preferably 0. At this time, R ²⁰¹ is preferably an alkyl group, and more preferably a methyl group.
In the general formula (3), when x1 and x2 are 0 and x3 is 1, y1 to y6 are preferably 0, y7 is 1, and y8 is preferably 0. At this time, R ²⁰⁷ is preferably an aryl group, and more preferably a phenyl group.
In the general formula (3), when x1 to x3 are 0, y1 to y3 are preferably 0, y4 is preferably 0 or 1, and y5 to y8 are preferably 0. At this time, R ²⁰¹ is preferably a fluorine atom.

In the general formula (3), among the six-membered aromatic rings constituted by A ^A11 to A ^A33 , the number of nitrogen-containing rings is preferably 1 or less, and more preferably 0.

In the general formula (3), there is no limitation on the connection of each 6-membered aromatic ring, but it is preferably connected at the meta position or the para position, and at least a 6-membered aromatic ring represented by x1 , X2 is more preferably linked at the meta position, and all 6-membered aromatic rings are particularly preferably linked at the meta position.

Next, when R ¹⁰² is an aryl group or heteroaryl group, R ¹⁰² is particularly preferably a substituent represented by the following general formula (4).

(In the above formula, A ^A41 to A ^A69 each independently represent CH or a nitrogen atom, and are ring members constituting a 6-membered aromatic ring. R ²¹¹ to R ²¹⁵ are each independently an alkyl group, a fluorine atom, a silyl group or an amino group, y11 ~ y14 are each independently represent an integer of 0 to 4, y15 is .R ²¹⁶ ~ R ²²⁰ represents an integer of 0 to 5 each independently represent an aryl group or a heteroaryl group , Y16 to y20 each independently represents an integer of 0 to 2, provided that the sum of y11 and y16, the sum of y12 and y17, the sum of y13 and y18, and the sum of y14 and y19 is a maximum of 4, (The sum of y20 is at most 5. x11, x12, x13 and x14 each independently represent 0 or 1, and x11 ≦ x12 ≦ x13 ≦ x14.)

In the general formula (4), the preferred range of R ²¹¹ to R ^{215 is the same as} the preferred range of the alkyl group, fluorine atom or silyl group as R ¹⁰¹ and R ¹⁰² in the general formula (1). However, it may be a substituted or unsubstituted amino group. Among these, R ²¹¹ to R ²¹⁵ are preferably an alkyl group, a fluorine atom, a silyl group or an amino group, and more preferably an alkyl group, a fluorine atom or a silyl group.
In the general formula (4), the preferred range of R ²¹⁶ to R ^{220 is the same as} the preferred range of the aryl group or heteroaryl group as R ¹⁰¹ and R ¹⁰² in the general formula (1). Among these, R ²¹⁶ to R ²²⁰ are preferably aryl groups, and more preferably phenyl groups.

In the general formula (4), the sum of y16 to y20, that is, the number of branches of the 6-membered aromatic ring in R ¹⁰² is preferably 0 to 2, more preferably 0 or 1. Particularly preferred is 0.

In the general formula (4), when x11 to x14 are 1, y11 is preferably 0, y12 is preferably 0 or 1, and y13 to y20 are preferably 0. When y12 is 1, R ²¹² is preferably an alkyl group, preferably an alkyl group substituted with a fluorine atom, more preferably a perfluoroalkyl group, and a C 3 perfluoroalkyl group. It is particularly preferred that
In the general formula (4), when x11 is 0 and x12 to x14 are 1, y12 is preferably 0 or 1, y13 is preferably 0, and y14 is 0 or 1. Y15 and y17 are preferably 0, y18 is preferably 0 or 1, and y19 and y20 are preferably 0. At this time, R ²¹² and R ²¹⁴ are preferably each independently an alkyl group, and more preferably a t-butyl group. R ²¹⁸ is preferably an aryl group, preferably an aryl group substituted with a fluorine atom, more preferably a perfluoroaryl group, and particularly preferably a C 6 perfluoroaryl group. .
In the general formula (4), when x11 and x12 are 0 and x13 and x14 are 1, y13 is preferably 0 or 1, y14 is preferably 0, and y15 is 0 or 1 Y18 and y19 are preferably 0 or 1, and y20 is preferably 0. At this time, R ²¹³ is preferably an alkyl group, a fluorine atom or a silyl group, more preferably an alkyl group substituted with a fluorine atom, a silyl group substituted with a fluorine atom or an alkyl group, and perfluoromethyl. A group, a fluorine atom, or a trimethylsilyl group is particularly preferable. R ²¹⁵ is preferably an alkyl group, more preferably an isopropyl group. R ²¹⁸ and R ²¹⁹ are preferably each independently an aryl group, and more preferably a phenyl group.
In the general formula (4), when x11 to X13 are 0 and x14 is 1, y14 is preferably 0 to 2, y15 is preferably 0 to 2, and y19 is 0 to 2 And y20 is preferably 0. At this time, R ²¹⁴ is preferably an alkyl group or a silyl group, more preferably a C 1-3 alkyl group or a silyl group substituted with an alkyl group, a methyl group, an isopropyl group or a dimethylphenylsilyl group. Particularly preferred is a group. R ²¹⁵ is preferably an alkyl group, a silyl group or an amino group, and is substituted with a silyl group or an aryl group substituted with a linear or branched alkyl group, cycloalkyl group or aryl group having 1 to 4 carbon atoms. And more preferably a triphenylmethyl group, a methylphenylethyl group, an isopropyl group, an n-propyl group, a t-butyl group, a cyclohexyl group, a triphenylsilyl group, or 3 ′, 5′-dimethyl. Biphenylene substituted amino groups are particularly preferred. R ²¹⁵ is preferably an aryl group, and more preferably a phenyl group.
In the general formula (4), when x11 to X14 are 0, y15 is preferably 0 to 2, and y20 is preferably 0. At this time, R ²¹⁵ is preferably an alkyl group, more preferably a methyl group or a t-butyl group.

In the general formula (4), among the 6-membered aromatic rings constituted by A ^A41 to A ^A69 , the number of nitrogen-containing rings is preferably 1 or less, and more preferably 0.

In the general formula (4), the connection of each 6-membered aromatic ring is not limited, but is preferably connected at the meta or para position, and at least a 6-membered aromatic ring represented by x11 More preferably, the six-membered aromatic ring represented by x12 is linked at the para position. However, the number of 6-membered aromatic rings linked at the para position is preferably 3 or less.

R ¹⁰¹ in the general formula (1) is a fluorine atom, a fluoroalkyl group, a cycloalkyl group, a silyl group, an alkylsilyl group, an arylsilyl group, a substituent containing a cycloalkylene group or a silicon atom linking group (the above-mentioned specific substituent). Any of the groups) may be included, but an embodiment not including any of the specific substituents may be used. In the present invention, an embodiment in which R ¹⁰¹ in the general formula (1) includes a fluorine atom, a fluoroalkyl group, or an alkylsilyl group, or an embodiment that does not include any one of the specific substituents is preferable. The aspect which does not contain is more preferable.

R ¹⁰¹ in the general formula (1) is preferably an aryl group which may have a substituent among an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group, and represented by the general formula (3). An aryl group in which X1 in the general formula (3) is 0, X2 and X3 are 1 is particularly preferable, and y1 to y8 in the general formula (3) are all 0 The group is particularly preferred, and unsubstituted m-terphenylene is even more particularly preferred.

R ¹⁰² in the general formula (1) is a fluorine atom, a fluoroalkyl group, a cycloalkyl group, a silyl group, an alkylsilyl group, an arylsilyl group, a substituent containing a cycloalkylene group or a silicon atom linking group (the above-mentioned specific substituent). In the present invention, an embodiment in which R ¹⁰² in the general formula (1) includes a fluorine atom, a fluoroalkyl group, a cycloalkyl group, or an alkylsilyl group is preferable. The embodiment containing an alkylsilyl group or an arylsilyl group is more preferred, and the embodiment containing an alkylsilyl group or an arylsilyl group is particularly preferred.

R ¹⁰² in the general formula (1) is an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group, an optionally substituted heteroaryl group or an optionally substituted aryl. Group is preferable, and the aryl group represented by the general formula (4) is particularly preferable.

In the general formula (3) or (4), the number of 6-membered monocycles linked at the para position is preferably 3 or less. For example, when a 6-membered monocycle is further linked to the end of the p-terphenylene group, it is preferably linked at the meta position or ortho position, more preferably at the meta position.

<N101 and n102 of general formula (1)>
In the general formula (1), n ₁₀₁ represents an integer of 0 to 11, preferably an integer of 0 to 2, particularly preferably 0 or 1, and more preferably 0.
In the general formula (1), when n ₁₀₁ is not 0, the position where the R ¹⁰¹ is substituted with the triphenylene ring structure is not particularly limited, but in the general formula (1), the triphenylene ring is connected to the biphenylene structure. It preferably has a substituent R ^{101 in} addition to the ring.

In the general formula (1), n ₁₀₂ represents an integer of 0 to 7, preferably an integer of 1 to 6, particularly preferably an integer of 1 to 5, and an integer of 1 to 2. More particularly preferred.
In the general formula (1), when n ₁₀₂ is not 0, the position where the R ¹⁰² is substituted with the biphenylene structure is not particularly limited, but is bonded to the triphenylene structure in the biphenylene structure of the general formula (1). preferably has at least one substituent R ¹⁰² to monocyclic no side 6-membered ring, on the side not bonded to the monocyclic and triphenylene structure 6 membered ring on the side which is bound to a triphenylene ring structure 6 it is preferred to have at least one substituent R ¹⁰² to both monocyclic membered ring.
Furthermore, at least one monocyclic aromatic ring (both aromatic rings are represented by both a 6-membered monocyclic ring bonded to the triphenylene ring structure and a 6-membered monocyclic ring not bonded to the triphenylene structure). And the ring member is particularly preferably a 6-membered ring composed of a carbon atom or a nitrogen atom).

In the charge transport material of the present invention, the compound represented by the general formula (1) is preferably represented by the following general formula (2).

In the general formula (2), R ¹¹¹ each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group, and may be further substituted with these groups or amino groups. R ²³¹ to R ²³⁴ each independently represents an alkyl group, a fluorine atom, a silyl group or an amino group. R ²³⁵ to R ²³⁸ each independently represents an aryl group or a heteroaryl group. However, R ¹¹¹ and R ²³¹ to R ²³⁸ do not include a condensed ring aryl structure or a condensed ring heteroaryl structure. R ¹¹¹ and R ²³¹ to R ²³⁸ include a total of 3 to 6 monocyclic aromatic rings (the aromatic ring is a 6-membered ring composed of a carbon atom or a nitrogen atom). n ₁₁₁ represents an integer of 0 to 11, y31 to y33 and y35 to y37 each independently represents an integer of 0 to 4, and y34 and y38 each represents an integer of 0 to 5. The plurality of R ¹¹¹ and R ²³¹ to R ²³⁸ may be the same or different. A ^B1 to A ^B17 each independently represent CH (the hydrogen atom of CH may be substituted with R ²³¹ to R ²³⁸ ) or a nitrogen atom, and are ring members constituting a 6-membered aromatic ring.

The preferred ranges of R ¹¹¹ and n ₁₁₁ in the general formula (2) are the same as the preferred ranges of R ¹⁰¹ and n ₁₀₁ in the general formula (1), respectively.

In the general formula (2), the preferred range of each 6-membered monocycle including A ^B1 to A ^B17 is the preferred range of the aryl group or heteroaryl group as R ¹⁰¹ and R ¹⁰² in the general formula (1). It is the same.

In the general formula (2), a preferred range of R ²³¹ to R ^{234 is} a preferred range of an alkyl group, aryl group, heteroaryl group, fluorine atom or silyl group as R ¹⁰¹ and R ¹⁰² in the general formula (1). It is the same. R ²³¹ to R ²³⁴ may be a substituted or unsubstituted amino group. Among them, R ²³¹ to R ²³⁴ are preferably an alkyl group, an aryl group, a fluorine atom or a silyl group, and more preferably a silyl group.
In the general formula (2), the preferred range of R ²³⁵ to R ^{238 is the same as} the preferred range of the aryl group or heteroaryl group as R ¹⁰¹ and R ¹⁰² in the general formula (1). Among them, R ²³⁵ to R ²³⁸ are preferably aryl groups, and more preferably p-terphenylene groups.

In the general formula (2), the sum of y35 to y38 is preferably 0 to 3, more preferably 0 to 2, and particularly preferably 0 to 1.

In the general formula (2), y31 is preferably 0 or 1. At this time, R ²³¹ is preferably an alkyl group or a silyl group, more preferably a methyl group or an aryl group-substituted silyl group, particularly preferably a methyl group or a triphenylsilyl group, and a triphenylsilyl group. A group (however, it is also preferable to further have 1 or 2 phenyl groups as a substituent) is more preferable.
In the general formula (2), y32 is preferably 0 to 3, more preferably 0 or 1. At this time, R ²³² is preferably an alkyl group, a fluorine atom, a silyl group, or an amino group, and an unsubstituted or substituted alkyl group substituted with a fluorine atom, a fluorine atom, an alkyl group, or an aryl group, or It is more preferably an amino group substituted with a phenyl group, and a methyl group, a fluorine atom, a trifluoromethyl group, a trimethylsilyl group, a triphenylsilyl group or an amino group is a group substituted with two phenyl groups. Particularly preferred is a methyl group, a fluorine atom or a trimethylsilyl group.
In the general formula (2), y33 is preferably 0 or 1. At this time, R ²³³ is preferably a silyl group, more preferably a silyl group substituted with at least one of an alkyl group and an aryl group, and a silyl group substituted with an alkyl group and an aryl group. Particularly preferred is a silyl group substituted with a methyl group and a phenyl group, and more preferred is a silyl group.
In formula (2), it is preferable that y34 is 0 or 1, this time, R ²³⁴ is substituted with an alkyl group, preferably a silyl group or an amino group, an alkyl group or an aryl group or a phenyl group The silyl group is more preferably an ethyl group (which may further have a substituent), n-propyl group, isopropyl group, t-butyl group, trimethylsilyl group, triphenylsilyl group or amino group. It is more particularly preferred that it is a group substituted with a number of biphenyls (which may further have a methyl group as a substituent).

In the general formula (2), y35 is preferably 0 or 1. At this time, R ²³⁵ is preferably an aryl group, more preferably a phenyl group, a biphenyl group, an m-terphenyl group, a p-terphenyl group, or a group in which these groups are further substituted. The further substituent is preferably an alkyl group, a fluorine atom, a silyl group or an aryl group, more preferably a trifluoromethyl group, a triphenylmethyl group, an isopropyl group, a t-butyl group, a trimethylsilyl group or a phenyl group.
In the general formula (2), y36 is preferably 0 or 1. At this time, R ²³⁶ is preferably an aryl group, more preferably a phenyl group, a dimethylphenyl group, a group in which a biphenyl group is substituted with two phenyl groups, or a p-terphenylene group, a phenyl group, Or it is particularly preferably a p-terphenylene group.
In the general formula (2), y37 is preferably 0.
In the general formula (2), y38 is preferably 0 or 1. In this case, R ²³⁸ is preferably an aryl group, more preferably a phenyl group, a biphenyl group, or a p-terphenylene group.

In the general formula (2), among the 6-membered aromatic rings constituted by A ^B1 to A ^B17 , the number of nitrogen-containing rings is preferably 1 or less, and more preferably 0.

In the general formula (2), the connection of each 6-membered aromatic ring is not limited, but is preferably connected at the meta position or the para position.
In the present invention, the A ^B3 in the general formula (2) preferably represents CH, and the hydrogen atom of the A ^B3 is preferably substituted by at least one of the R ²³⁵ .

In the compound represented by the general formula (1), it is preferable that all monocyclic aromatic rings included in the general formula (1) are 6-membered rings of a carbon atom skeleton, and only carbon atoms and hydrogen atoms are included. More preferably, it consists of.

Furthermore, the compound represented by the general formula (1) has a monocyclic aromatic ring (the aromatic ring is a six-membered ring composed of a carbon atom or a nitrogen atom) via a single bond. It has at least one partial structure that is continuously connected by 4 or more, and the number of monocyclic aromatic rings continuously connected at the para position in the partial structure is 3 or less. Is preferable from the viewpoint of using a green phosphorescent material. Note that this description does not exclude from the present invention an embodiment in which the number of monocyclic aromatic rings continuously connected at the para position is 4, but the above-mentioned continuously connected at the para position. A compound having four monocyclic aromatic rings is preferred from the viewpoint of using a red phosphorescent material.
Furthermore, the compound represented by the general formula (1) includes three aromatic rings continuously connected at the para position including a phenyl ring which is a partial structure of a condensed ring constituting a triphenylene ring. The following is preferable.

The T ₁ energy in the film state of the compound represented by the general formula (1) is preferably 2.39 eV (55.0 kcal / mol) or more and 3.25 eV (75.0 kcal / mol) or less. It is more preferable that it is 0.47 eV (57.0 kcal / mol) or more and 3.04 eV (70.0 kcal / mol) or less, and 2.52 eV (58.0 kcal / mol) or more and 2.82 eV (65.0 kcal / mol) or less. More preferably. In particular, when a phosphorescent light emitting material is used as the light emitting material, the T ₁ energy is preferably in the above range.

The T ₁ energy can be determined from the short wavelength end of a phosphorescence emission spectrum of a thin film of material. For example, a material is deposited on a cleaned quartz glass substrate to a thickness of about 50 nm by vacuum deposition, and the phosphorescence emission spectrum of the thin film is measured at F-7000 Hitachi Spectrofluorimeter (Hitachi High Technologies) under liquid nitrogen temperature. Use to measure. T ₁ energy can be obtained by converting the rising wavelength on the short wavelength side of the obtained emission spectrum into energy units.

In the charge transport material of the present invention, the molecular weight of the compound represented by the general formula (1) is preferably 1200 or less, more preferably 1000 or less, and further preferably 750 or more and 1000 or less. 750 to 900, particularly preferably 750 to 850. By setting the molecular weight within this range, a material having good film quality and excellent sublimation purification / deposition suitability can be obtained.

The glass transition temperature (Tg) of the compound represented by the general formula (1) is 80 ° C. or higher and 400 ° C. or lower from the viewpoint of stably operating the organic electroluminescent device against heat generated during high temperature driving or driving the device. Preferably, the temperature is 100 ° C. or higher and 400 ° C. or lower, more preferably 120 ° C. or higher and 400 ° C. or lower.

Specific examples of the compound represented by the general formula (1) are shown below, but the present invention is not limited thereto.

The compounds represented by the above general formula (1) are disclosed in JP-A No. 2004-43349, JP-A No. 2004-83481, US 2006/0280965, WO 2009/021107, JP-A 2009-111068, Special Table 2010-535806. It can synthesize | combine combining the method as described in gazette etc., and other well-known reaction.
After synthesis, it is preferable to purify by sublimation purification after purification by column chromatography, recrystallization or the like. By sublimation purification, not only can organic impurities be separated, but inorganic salts and residual solvents can be effectively removed.

[Organic electroluminescence device]
The organic electroluminescent element of the present invention has a substrate, a pair of electrodes including an anode and a cathode disposed on the substrate, and an organic layer disposed between the electrodes, and the organic layer emits phosphorescence. It contains the material and the charge transport material of the present invention, that is, the compound represented by the general formula (1).

The structure of the organic electroluminescent element of the present invention is not particularly limited. In FIG. 1, an example of a structure of the organic electroluminescent element of this invention is shown. 1 has an organic layer on a substrate 2 between a pair of electrodes (anode 3 and cathode 9).
The element configuration, the substrate, the cathode, and the anode of the organic electroluminescence element are described in detail in, for example, Japanese Patent Application Laid-Open No. 2008-270736, and the matters described in the publication can be applied to the present invention.
Hereinafter, the preferable aspect of the organic electroluminescent element of this invention is demonstrated in detail in order of a board | substrate, an electrode, an organic layer, a protective layer, a sealing container, a drive method, light emission wavelength, and a use.

<Board>
The organic electroluminescent element of the present invention has a substrate.
The substrate used in the present invention is preferably a substrate that does not scatter or attenuate light emitted from the organic layer. In the case of an organic material, it is preferable that it is excellent in heat resistance, dimensional stability, solvent resistance, electrical insulation, and workability.

<Electrode>
The organic electroluminescent element of the present invention is disposed on the substrate and has a pair of electrodes including an anode and a cathode.
In view of the properties of the light-emitting element, at least one of the pair of electrodes, the anode and the cathode, is preferably transparent or translucent.

(anode)
The anode usually only needs to have a function as an electrode for supplying holes to the organic layer, and there is no particular limitation on the shape, structure, size, etc., depending on the use and purpose of the light-emitting element, It can select suitably from well-known electrode materials. As described above, the anode is usually provided as a transparent anode.

(Cathode) The cathode need only normally have a function as an electrode for injecting electrons into the organic layer, and there is no particular limitation on the shape, structure, size, etc., depending on the use and purpose of the light-emitting element. Thus, it can be appropriately selected from known electrode materials.

<Organic layer>
The organic electroluminescent element of the present invention has an organic layer disposed between the electrodes, and the organic layer includes a phosphorescent material and a compound represented by the general formula (1).
There is no restriction | limiting in particular in the said organic layer, Although it can select suitably according to the use and objective of an organic electroluminescent element, It is preferable to form on the said transparent electrode or the said semi-transparent electrode. In this case, the organic layer is formed on the entire surface or one surface of the transparent electrode or the semitransparent electrode.
There is no restriction | limiting in particular about the shape of a organic layer, a magnitude | size, thickness, etc., According to the objective, it can select suitably.
Hereinafter, in the organic electroluminescent element of the present invention, the configuration of the organic layer, the method for forming the organic layer, preferred embodiments of the layers constituting the organic layer, and materials used for the layers will be described in order.

(Organic layer structure)
In the organic electroluminescent element of the present invention, the organic layer preferably includes a charge transport layer. The charge transport layer refers to a layer in which charge transfer occurs when a voltage is applied to the organic electroluminescent element. Specific examples include a hole injection layer, a hole transport layer, an electron block layer, a light emitting layer, a hole block layer, an electron transport layer, and an electron injection layer. If the charge transport layer is a hole injection layer, a hole transport layer, an electron block layer, or a light emitting layer, it is possible to manufacture an organic electroluminescent element with low cost and high efficiency.
The organic electroluminescent element of the present invention preferably has a light emitting layer containing the phosphorescent material and another organic layer, and the light emitting layer contains the compound represented by the general formula (1). Furthermore, in the organic electroluminescent element of the present invention, it is more preferable that the organic layer has a light emitting layer containing the phosphorescent material and another organic layer. However, in the organic electroluminescent element of the present invention, even when the organic layer has a light emitting layer and other organic layers, the layers do not necessarily have to be clearly distinguished.

In the organic electroluminescent element of the present invention, the organic layer contains a phosphorescent material and a compound represented by the general formula (1). At this time, there is no particular limitation on the place where the phosphorescent material and the compound represented by the general formula (1) are included. In this invention, it is more preferable that the said organic layer has the light emitting layer containing the said phosphorescence-emitting material, and another organic layer, and the said light emitting layer contains the compound represented by the said General formula (1). At this time, it is preferable that the compound represented by the general formula (1) is used as a host material of the light emitting layer (hereinafter also referred to as a host compound).

The compound represented by the general formula (1) may be contained in any organic layer between the cathode and the anode of the organic electroluminescent element.
As an organic layer which may contain the compound represented by the general formula (1), a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an exciton block layer, a charge block Layer (a hole block layer, an electron block layer, etc.), etc., preferably a light emitting layer, an exciton block layer, a charge block layer, an electron transport layer, an electron injection layer, more preferably A light emitting layer, an exciton blocking layer, a charge blocking layer, or an electron transport layer, particularly preferably a light emitting layer, a hole blocking layer, an electron blocking layer, more particularly preferably a light emitting layer or a hole blocking layer, More particularly preferred is a light emitting layer.

When the compound represented by the general formula (1) is contained in the light emitting layer, it is preferably contained in an amount of 0.1 to 99% by weight, preferably 1 to 95% by weight, based on the total weight of the light emitting layer. Is more preferable, and 10 to 95% by mass is more preferable.

The maximum emission wavelength of the light emitting material using the compound represented by the general formula (1) is preferably 400 to 700 nm, more preferably 500 to 700 nm, and particularly preferably 500 to 650 nm. More preferably, it is 500 to 550 nm, and most preferably 520 to 550 nm.

Further, the electron transport layer or the hole blocking layer (more preferably, the hole blocking layer) is provided between the pair of electrodes, and the electron transport layer or the hole blocking layer is represented by the general formula (1). It is also preferable to contain a compound to be prepared.
When the compound represented by the general formula (1) is contained in an organic layer other than the light emitting layer, it is preferably contained in an amount of 70 to 100% by mass, and 85 to 100% by mass with respect to the total mass of the organic layer. More preferably it is included.

These organic layers may be provided in a plurality of layers, and when a plurality of layers are provided, they may be formed of the same material or different materials for each layer.

(Formation method of organic layer)
In the organic electroluminescence device of the present invention, each organic layer is formed by a dry film forming method such as a vapor deposition method or a sputtering method, a wet film forming method such as a transfer method, a printing method, a spin coating method, or a bar coating method (solution coating method). Any of these can be suitably formed.
In the organic electroluminescent element of the present invention, the organic layer disposed between the pair of electrodes includes at least one layer formed by vapor deposition of a composition containing the compound represented by the general formula (1). Is preferred.

(Light emitting layer)
The light emitting layer receives holes from the anode, hole injection layer or hole transport layer and receives electrons from the cathode, electron injection layer or electron transport layer when an electric field is applied, and provides a field for recombination of holes and electrons. And a layer having a function of emitting light. However, the light emitting layer in the present invention is not necessarily limited to light emission by such a mechanism. The light emitting layer in the organic electroluminescent element of the present invention preferably contains at least one phosphorescent material.

The light emitting layer in the organic electroluminescent device of the present invention may be composed only of the light emitting material, or may be a mixed layer of a host material and the light emitting material. The kind of the light emitting material may be one kind or two kinds or more. The host material is preferably a charge transport material. The host material may be one kind or two or more kinds, and examples thereof include a configuration in which an electron transporting host material and a hole transporting host material are mixed. Furthermore, the light emitting layer may include a material that does not have charge transporting properties and does not emit light.

Further, the light emitting layer may be a single layer or a multilayer of two or more layers, and each layer may contain the same light emitting material or host material, or each layer may contain a different material. When there are a plurality of light emitting layers, each of the light emitting layers may emit light with different emission colors.

The thickness of the light emitting layer is not particularly limited, but is usually preferably 2 nm to 500 nm, and more preferably 3 nm to 200 nm, and more preferably 5 nm to 100 nm from the viewpoint of external quantum efficiency. More preferably.

In the organic electroluminescent element of the present invention, it is preferable that the light emitting layer contains a compound represented by the general formula (1), and the host material of the light emitting layer is represented by the general formula (1). It is a more preferable embodiment to use a compound. Here, in this specification, the host material is a compound mainly responsible for charge injection and transport in the light emitting layer, and is a compound that itself does not substantially emit light. Here, “substantially does not emit light” means that the amount of light emitted from the compound that does not substantially emit light is preferably 5% or less, more preferably 3% or less of the total amount of light emitted from the entire device. Preferably it says 1% or less.
Hereinafter, as the material of the light emitting layer, the host material other than the light emitting material and the compound represented by the general formula (1) will be described in order. In addition, the compound represented by the said General formula (1) may be used other than the said light emitting layer in the organic electroluminescent element of this invention.

(Luminescent material)
As the light emitting material in the present invention, any of phosphorescent light emitting materials, fluorescent light emitting materials and the like can be used.
The light emitting layer in the present invention can contain two or more kinds of light emitting materials in order to improve the color purity and broaden the light emission wavelength region. At least one of the light emitting materials is preferably a phosphorescent light emitting material.
In the present invention, in addition to at least one phosphorescent light-emitting material contained in the light-emitting layer, a fluorescent light-emitting material or a phosphorescent light-emitting material different from the phosphorescent light-emitting material contained in the light-emitting layer can be used as the light-emitting material.
Details of these fluorescent materials and phosphorescent materials are described in, for example, paragraph numbers [0100] to [0164] of JP-A-2008-270736 and paragraph numbers [0088] to [0090] of JP-A-2007-266458. The matters described in these publications can be applied to the present invention.

Examples of phosphorescent light-emitting materials that can be used in the present invention include US Pat. / 19373A2, JP-A No. 2001-247859, JP-A No. 2002-302671, JP-A No. 2002-117978, JP-A No. 2003-133074, JP-A No. 2002-1235076, JP-A No. 2003-123684, JP-A No. 2002-170684, EP No. 121157, JP-A No. 2002 -226495, JP 2002-234894, JP 2001-247859, JP 2001-298470, JP 2002-1736 4, JP2002-203678, JP2002-203679, JP2004-357679, JP2006-256999, JP2007-19462, JP2007-84635, JP2007-96259, WO07 / 095118, WO10 / 111175, WO10 / 027583, WO10 / 028151, and the like, and phosphorescent compounds described in patent documents such as WO10 / 028151 are mentioned. Among them, more preferable luminescent materials include iridium (Ir) complexes, platinum (Pt) complexes, Cu complexes, and Re complexes. , W complexes, Rh complexes, Ru complexes, Pd complexes, Os complexes, Eu complexes, Tb complexes, Gd complexes, Dy complexes, and Ce complexes. Particularly preferred is an iridium (Ir) complex, a platinum (Pt) complex, or a Re complex. Among them, at least one coordination mode of a metal-carbon bond, a metal-nitrogen bond, a metal-oxygen bond, or a metal-sulfur bond is used. An iridium (Ir) complex, a platinum (Pt) complex, or a Re complex is preferable. Furthermore, iridium (Ir) complex and platinum (Pt) complex are particularly preferable, and iridium (Ir) complex is most preferable from the viewpoint of luminous efficiency, driving durability, chromaticity and the like.

The phosphorescent material contained in the light emitting layer in the present invention includes an iridium (Ir) complex represented by the following general formula (E-1) or platinum represented by the following general formula (C-1) It is preferable to use a (Pt) complex.

The iridium (Ir) complex represented by the general formula (E-1) will be described.

In general formula (E-1), Z ¹ and Z ² each independently represents a carbon atom or a nitrogen atom.
A ₁ represents an atomic group that forms a 5- or 6-membered heterocycle with Z ¹ and a nitrogen atom.
B ₁ represents an atomic group that forms a 5- or 6-membered ring with Z ² and a carbon atom.
(XY) represents a monoanionic bidentate ligand.
n _E1 represents an integer of 1 to 3. When n _E1 is 2 or 3, there will be 2 or 3 ligands containing Z ¹ , Z ² , A ₁ and B ₁ , They may be the same or different from each other.

n _E1 represents an integer of 1 to 3, preferably 2 or 3, and more preferably 3.
Z ¹ and Z ² each independently represents a carbon atom or a nitrogen atom. Z ¹ and Z ² are preferably carbon atoms.

A ₁ represents an atomic group that forms a 5- or 6-membered heterocycle with Z ¹ and a nitrogen atom. Examples of the 5- or 6-membered heterocycle containing A ₁ , Z ¹ and a nitrogen atom include a pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring, triazole ring, oxadiazole Ring, thiadiazole ring and the like.
From the viewpoint of the stability of the complex, emission wavelength control and emission quantum yield, the 5- or 6-membered hetero ring formed by A ₁ , Z ¹ and a nitrogen atom is preferably a pyridine ring, a pyrazine ring, an imidazole ring or a pyrazole. A ring, more preferably a pyridine ring, an imidazole ring and a pyrazine ring, still more preferably a pyridine ring and an imidazole ring, and most preferably a pyridine ring.

The 5- or 6-membered heterocycle formed by A ₁ , Z ¹ and a nitrogen atom may have a substituent, and as a substituent on the carbon atom, the following substituent group A is on the nitrogen atom. The following substituent group B can be applied as the substituent. The substituent on carbon is preferably an alkyl group, a perfluoroalkyl group, an aryl group, a heteroaryl group, a dialkylamino group, a diarylamino group, an alkoxy group, a cyano group, or a fluorine atom.

<< Substituent group A >>
An alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, isopropyl, t-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), alkenyl groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as vinyl , Allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms such as propargyl , 3-pentynyl, etc.), aryl groups (preferably having 6 to 30 carbon atoms, more preferably 6 to 0, particularly preferably 6 to 12 carbon atoms, such as phenyl, p-methylphenyl, naphthyl, anthryl, etc.), an amino group (preferably 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms). Particularly preferably 0 to 10 carbon atoms, such as amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino, ditolylamino, etc.), an alkoxy group (preferably having 1 to 30 carbon atoms, Preferably it has 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, and examples thereof include methoxy, ethoxy, butoxy, 2-ethylhexyloxy, etc.), an aryloxy group (preferably having 6 to 30 carbon atoms, More preferably, it has 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms. And 1-naphthyloxy, 2-naphthyloxy, etc.), a heterocyclic oxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms). For example, pyridyloxy, pyrazinyloxy, pyrimidinyloxy, quinolyloxy, etc.), acyl groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, Acetyl, benzoyl, formyl, pivaloyl, etc.), an alkoxycarbonyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms such as methoxycarbonyl, Ethoxycarbonyl, etc.), aryloxycarbonyl group (preferably carbon It has 7 to 30, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, and examples thereof include phenyloxycarbonyl. ), An acyloxy group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as acetoxy, benzoyloxy, etc.), an acylamino group (preferably 2-30 carbon atoms, more preferably 2-20 carbon atoms, particularly preferably 2-10 carbon atoms, and examples thereof include acetylamino, benzoylamino and the like, and alkoxycarbonylamino groups (preferably having 2-2 carbon atoms). 30, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonylamino, etc.), an aryloxycarbonylamino group (preferably having 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, for example phenyloxycarbonyl And sulfonylamino groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfonylamino and benzenesulfonylamino). ), A sulfamoyl group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 12 carbon atoms, such as sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenyl Sulfamoyl, etc.), carbamoyl groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as carbamoyl, methylcarbamoyl, diethylcarbamoyl, Phenylcarbamoyl etc.), alkylthio group ( Preferably, it has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methylthio, ethylthio, etc.), an arylthio group (preferably 6 to 30 carbon atoms). More preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenylthio, etc.), a heterocyclic thio group (preferably 1 to 30 carbon atoms, more preferably 1 to carbon atoms). 20, particularly preferably 1 to 12 carbon atoms, such as pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio and the like, and a sulfonyl group (preferably having a carbon number of 1 to 30, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include mesyl and tosyl). Rufinyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include methanesulfinyl and benzenesulfinyl. ), Ureido groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as ureido, methylureido, phenylureido, etc.), phosphoric acid An amide group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms such as diethyl phosphoric acid amide and phenylphosphoric acid amide), a hydroxy group , Mercapto group, halogen atom (eg fluorine atom, chlorine atom, bromine atom, iodine atom), cyano group, sulfo group, carboxyl group, nitro group, hydroxamic acid group, sulfino group, hydrazino group, imino group, heterocyclic group ( Heteroaryl groups are also included, preferably having 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms. Is, for example, a nitrogen atom, oxygen atom, sulfur atom, phosphorus atom, silicon atom, selenium atom, tellurium atom, specifically pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, And isoxazolyl, isothiazolyl, quinolyl, furyl, thienyl, selenophenyl, tellurophenyl, piperidyl, piperidino, morpholino, pyrrolidyl, pyrrolidino, benzoxazolyl, benzoimidazolyl, benzothiazolyl, carbazolyl group, azepinyl group, silolyl group and the like. Silyl group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, and examples thereof include trimethylsilyl and triphenylsilyl). A silyloxy group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, such as trimethylsilyloxy, triphenylsilyloxy, etc.), phosphoryl group (for example, A diphenylphosphoryl group, a dimethylphosphoryl group, etc.). These substituents may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above. Moreover, the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above. Moreover, the substituent substituted by the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above.

<< Substituent group B >>
An alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methyl, ethyl, isopropyl, t-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), alkenyl groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as vinyl , Allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms such as propargyl , 3-pentynyl, etc.), aryl groups (preferably having 6 to 30 carbon atoms, more preferably 6 to 0, particularly preferably 6 to 12 carbon atoms, including phenyl, p-methylphenyl, naphthyl, anthryl, etc.), cyano group, heterocyclic group (including heteroaryl groups, preferably 1 carbon atom) To 30 and more preferably 1 to 12 carbon atoms, and examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, a silicon atom, a selenium atom, and a tellurium atom. Specifically, pyridyl, pyrazinyl , Pyrimidinyl, pyridazinyl, pyrrolyl, pyrazolyl, triazolyl, imidazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, quinolyl, furyl, thienyl, selenophenyl, tellurophenyl, piperidyl, piperidino, morpholino, pyrrolidyl, pyrrolidino, benzoxazolyl, benzimidazolyl, Nzothiazolyl, carbazolyl group, azepinyl group, silylyl group, etc.) These substituents may be further substituted, and examples of the further substituent include groups selected from the above-mentioned substituent group A. . Moreover, the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above. Moreover, the substituent substituted by the substituent substituted by the substituent may be further substituted, and examples of the further substituent include a group selected from the substituent group A described above.

The substituent is appropriately selected for controlling the emission wavelength and potential, but in the case of shortening the wavelength, an electron donating group, a fluorine atom, and an aromatic ring group are preferable. For example, an alkyl group, a dialkylamino group, an alkoxy group, A fluorine atom, an aryl group, a heteroaryl group and the like are selected. In the case of increasing the wavelength, an electron withdrawing group is preferable, and for example, a cyano group, a perfluoroalkyl group, or the like is selected.

The substituent on the nitrogen is preferably an alkyl group, an aryl group, or a heteroaryl group, and an alkyl group or an aryl group is preferable from the viewpoint of the stability of the complex.
The substituents may be linked to form a condensed ring, and the formed ring includes a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, and a pyrazole. Ring, thiophene ring, furan ring and the like. These formed rings may have a substituent, and examples of the substituent include the substituent on the carbon atom and the substituent on the nitrogen atom.

B ₁ represents a 5- or 6-membered ring containing Z ² and a carbon atom. Examples of the 5- or 6-membered ring formed by B ₁ , Z ² and a carbon atom include a benzene ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a pyridazine ring, a triazine ring, an imidazole ring, a pyrazole ring, an oxazole ring, a thiazole ring, Examples include a triazole ring, an oxadiazole ring, a thiadiazole ring, a thiophene ring, and a furan ring.
From the viewpoint of the stability of the complex, emission wavelength control and emission quantum yield, the benzene ring, pyridine ring, pyrazine ring, imidazole ring, pyrazole is preferable as the 5- or 6-membered ring formed by B ₁ , Z ² and carbon atom. A ring and a thiophene ring, more preferably a benzene ring, a pyridine ring and a pyrazole ring, and still more preferably a benzene ring and a pyridine ring.

The 5- or 6-membered ring formed of B ₁ , Z ² and a carbon atom may have a substituent, and the substituent group A is a substituent on a nitrogen atom as a substituent on the carbon atom. As the above, the substituent group B can be applied. The substituent on carbon is preferably an alkyl group, a perfluoroalkyl group, an aryl group, a heteroaryl group, a dialkylamino group, a diarylamino group, an alkoxy group, a cyano group, or a fluorine atom.

The substituent is appropriately selected for controlling the emission wavelength and potential, but in the case of increasing the wavelength, an electron donating group and an aromatic ring group are preferable, for example, an alkyl group, a dialkylamino group, an alkoxy group, an aryl group, A heteroaryl group or the like is selected. In order to shorten the wavelength, an electron withdrawing group is preferable, and for example, a fluorine atom, a cyano group, a perfluoroalkyl group, and the like are selected.

The substituent on the nitrogen is preferably an alkyl group, an aryl group, or a heteroaryl group, and an alkyl group or an aryl group is preferable from the viewpoint of the stability of the complex. The substituents may be linked to form a condensed ring, and the formed ring includes a benzene ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, an imidazole ring, an oxazole ring, a thiazole ring, and a pyrazole. Ring, thiophene ring, furan ring and the like. These formed rings may have a substituent, and examples of the substituent include the substituent on the carbon atom and the substituent on the nitrogen atom.
In addition, a 5- or 6-membered heterocyclic substituent formed by A ₁ , Z ¹ and a nitrogen atom and a 5- or 6-membered substituent formed by B ₁ , Z ² and a carbon atom are linked. Then, the same condensed ring as described above may be formed.

As the ligand represented by (XY), there are various known ligands used in conventionally known metal complexes. For example, “Photochemistry and Photophysics of Coordination Compounds” Springer-Verlag H. Included in ligands (eg, halogen ligands (preferably chlorine ligands), etc., published in 1987, published by Yersin, “Organometallic Chemistry-Fundamentals and Applications-” Nitrogen heteroaryl ligands (for example, bipyridyl, phenanthroline, etc.) and diketone ligands (for example, acetylacetone, etc.) can be mentioned.

* Represents a coordination position to iridium (Ir).
The ligands represented by (XY) are preferably the following general formulas (l-1) to (l-13), but the present invention is not limited to these.

* Represents a coordination position to iridium (Ir) in the general formula (E-1). Rx, Ry and Rz each independently represents a hydrogen atom or a substituent. G represents CR or a nitrogen atom. R represents a hydrogen atom or a substituent.
When Rx, Ry, and Rz represent a substituent, examples of the substituent include a substituent selected from the substituent group A. Preferably, Rx and Rz are each independently an alkyl group, a perfluoroalkyl group, a fluorine atom or an aryl group, more preferably an alkyl group having 1 to 4 carbon atoms, a perfluoroalkyl group having 1 to 4 carbon atoms, A fluorine atom and an optionally substituted phenyl group are most preferred, and a methyl group, an ethyl group, a trifluoromethyl group, a fluorine atom and a phenyl group are most preferred. Ry is preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, a fluorine atom or an aryl group, more preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or an optionally substituted phenyl group. And most preferably a hydrogen atom or a methyl group. Since these ligands are considered not to be sites where electrons are transported in the device or where electrons are concentrated by excitation, Rx, Ry, and Rz may be any chemically stable substituent, and the effects of the present invention can be achieved. Also has no effect.
R ^l1 ~ R ^l7 in the general formula (I-13) is preferably represents a substituent selected from substituent group A, may further have a substituent A.
G represents CR or a nitrogen atom. When R represents a substituent, examples of the substituent include a substituent selected from the substituent group A.
When R ¹¹ to R ¹⁷ and G represent C—R, any two of them may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl , Aryl or heteroaryl, and the fused 4- to 7-membered ring may further have a substituent.
The preferred range of R ¹¹ to R ^{17 is the same as} the preferred range of R ^T1 to R ^T7 in general formula (E-3) described later.
G is preferably C—R, and R is preferably a hydrogen atom or an aryl group, more preferably a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms (for example, a phenyl group, a tolyl group, Naphthyl group, etc.), particularly preferably a hydrogen atom or a phenyl group.

(XY) is more preferably (l-1), (l-4), (l-13), and particularly preferably (l-1), (l-13). Complexes having these ligands can be synthesized in the same manner as in known synthesis examples by using corresponding ligand precursors. For example, it can be synthesized in the same manner as described in International Publication 2009-073245, page 46.

A preferred embodiment of the iridium (Ir) complex represented by the general formula (E-1) is an iridium (Ir) complex represented by the general formula (E-2).

In general formula (E-2), A ^E1 to A ^E8 each independently represents a nitrogen atom or C—R ^E.
R ^E represents a hydrogen atom or a substituent.
(XY) represents a monoanionic bidentate ligand.
n _E2 represents an integer of 1 to 3.

A ^E1 to A ^E8 each independently represent a nitrogen atom or C—R ^E. R ^E represents a hydrogen atom or a substituent, and R ^E may be connected to each other to form a ring. Examples of the ring formed include the same ring as the condensed ring described in the general formula (E-1). Examples of the substituent represented by R ^E, we are the same as those mentioned above substituent group A.
Preferred as A ^E1 ~ A ^E4 is C-R ^E, if A ^E1 ~ A ^E4 is C-R ^E, preferably a hydrogen atom R ^E of A ^E3, alkyl group, aryl group, amino group, An alkoxy group, an aryloxy group, a fluorine atom, or a cyano group, more preferably a hydrogen atom, an alkyl group, an amino group, an alkoxy group, an aryloxy group, or a fluorine atom, and particularly preferably a hydrogen atom or a fluorine atom. R ^E of A ^E1 , A ^E2 and A ^E4 is preferably a hydrogen atom, alkyl group, aryl group, amino group, alkoxy group, aryloxy group, fluorine atom or cyano group, more preferably a hydrogen atom, An alkyl group, an amino group, an alkoxy group, an aryloxy group, or a fluorine atom, particularly preferably a hydrogen atom.

A ^E5 to A ^E8 are preferably C—R ^E , and when A ^E5 to A ^E8 are C—R ^E , R ^E is preferably a hydrogen atom, an alkyl group, a perfluoroalkyl group, an aryl group, heteroaryl Group, dialkylamino group, diarylamino group, alkyloxy group, cyano group, or fluorine atom, more preferably a hydrogen atom, alkyl group, perfluoroalkyl group, aryl group, dialkylamino group, cyano group, or fluorine atom. And more preferably a hydrogen atom, an alkyl group, a trifluoromethyl group, or a fluorine atom. If possible, the substituents may be linked to form a condensed ring structure. When the emission wavelength is shifted to the short wavelength side, A ^E6 is preferably a nitrogen atom.
(X-Y), and n _E2 of the general formula in (E1) (X-Y) , and has the same meaning as n _E1 preferable ranges are also the same.

A more preferred form of the compound represented by the general formula (E-2) is a compound represented by the following general formula (E-3).

In the general formula (E-3), R ^T1 , R ^T2 , R ^T3 , R ^T4 , R ^T5 , R ^T6 and R ^T7 are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, —CN, perfluoroalkyl group, trifluorovinyl group, —CO ₂ R, —C (O) R, —NR ₂ , —NO ₂ , —OR, halogen atom, aryl group or heteroaryl group, and further substituents You may have. Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
A represents CR ′ or a nitrogen atom, and R ′ represents a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, —CN, a perfluoroalkyl group, a trifluorovinyl group, —CO ₂ R, —C (O ) R, —NR ₂ , —NO ₂ , —OR, a halogen atom, an aryl group or a heteroaryl group, which may further have a substituent. Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
R ^T1 to R ^T7 and R ′ may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl or heteroaryl The condensed 4- to 7-membered ring may further have a substituent. Of these, the case where R ^T1 and R ^T7 , or R ^T5 and R ^T6 are condensed to form a benzene ring is preferred, and the case where R ^T5 and R ^T6 are condensed to form a benzene ring is particularly preferred.
(XY) represents a monoanionic bidentate ligand. n _E3 represents an integer of 1 to 3.

The alkyl group may have a substituent, may be saturated or unsaturated, and examples of the group that may be substituted include the above-described substituent A. The alkyl group represented by R ^T1 to R ^T7 and R ′ is preferably an alkyl group having 1 to 8 carbon atoms in total, more preferably an alkyl group having 1 to 6 carbon atoms in total, such as methyl Group, ethyl group, i-propyl group, cyclohexyl group, t-butyl group and the like, and methyl group is particularly preferable.
The cycloalkyl group may have a substituent, may be saturated or unsaturated, and examples of the group that may be substituted include the above-described substituent A. The cycloalkyl group represented by R ^T1 to R ^T7 and R ′ is preferably a cycloalkyl group having 4 to 7 ring members, more preferably a cycloalkyl group having 5 to 6 carbon atoms in total. A cyclopentyl group, a cyclohexyl group, etc. are mentioned.
The alkenyl group represented by R ^T1 to R ^T7 and R ′ preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms. For example, vinyl, allyl, Examples include 1-propenyl, 1-isopropenyl, 1-butenyl, 2-butenyl, 3-pentenyl and the like.
The alkynyl group represented by R ^T1 to R ^T7 and R ′ preferably has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 10 carbon atoms. For example, ethynyl, propargyl , 1-propynyl, 3-pentynyl and the like.

Examples of the perfluoroalkyl group represented by R ^T1 to R ^T7 and R ′ include those in which all the hydrogen atoms of the aforementioned alkyl group are replaced with fluorine atoms.

The aryl group represented by R ^T1 to R ^T7 and R ′ is preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, such as a phenyl group, a tolyl group, a naphthyl group, etc. A phenyl group is particularly preferred.

The heteroaryl group represented by R ^T1 to R ^T7 and R ′ is preferably a heteroaryl group having 5 to 8 carbon atoms, more preferably a 5- or 6-membered substituted or unsubstituted heteroaryl group. Groups such as pyridyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, cinnolinyl, phthalazinyl, quinoxalinyl, pyrrolyl, indolyl, furyl, benzofuryl , Thienyl group, benzothienyl group, pyrazolyl group, imidazolyl group, benzimidazolyl group, triazolyl group, oxazolyl group, benzoxazolyl group, thiazolyl group, benzothiazolyl group, isothiazolyl group, benzisothiazolyl group, thiadiazolyl group, isoxazolyl group Benz Sookisazoriru group, a pyrrolidinyl group, a piperidinyl group, a piperazinyl group, an imidazolidinyl group, a thiazolinyl group, a sulfolanyl group, a carbazolyl group, a dibenzofuryl group, dibenzothienyl group, such as 7 pyrido-indolyl group. Preferred examples include pyridyl group, pyrimidinyl group, imidazolyl group, and thienyl group, and more preferred are pyridyl group and pyrimidinyl group.

R ^T1 to R ^T7 and R ′ are preferably a hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a perfluoroalkyl group, a dialkylamino group, a fluoro group, an aryl group, or a heteroaryl group, more preferably A hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a fluoro group, and an aryl group are preferable, and a hydrogen atom, an alkyl group, and an aryl group are more preferable.

Any two of R ^T1 to R ^T7 and R ′ may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl, or heteroaryl; The condensed 4- to 7-membered ring may further have a substituent. The definition and preferred range of cycloalkyl, aryl and heteroaryl formed are the same as the cycloalkyl group, aryl group and heteroaryl group defined by R ^T1 to R ^T7 and R ′.
Further, it is particularly preferable that A represents CR ′, and among R ^T1 to R ^T7 and R ′, 0 to 2 are alkyl groups or phenyl groups, and the rest are all hydrogen atoms, and R ^T1 to R ^T7 , And R ′ are particularly preferably 0 to 2 alkyl groups and the rest are all hydrogen atoms. Among R ^T1 to R ^T7 and R ′, 0 to 2 are methyl groups and the rest are all hydrogen atoms. Most preferred is an atom.

n _E3 is preferably 2 or 3. The type of ligand in the complex is preferably composed of 1 to 2 types, more preferably 2 types.
(XY) has the same meaning as (XY) in formula (E-1), and the preferred range is also the same.

One preferred form of the compound represented by the general formula (E-3) is a compound represented by the following general formula (E-4).

R ^T1 to R ^T4 , A, (XY) and n _E4 in the general formula (E-4) are R ^T1 to R ^T4 , A, (XY) and n _{E3 in the} general formula (E-3). The preferred range is also the same. R ₁ ′ to R ₅ ′ are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, alkynyl group, cyano group, perfluoroalkyl group, trifluorovinyl group, —CO ₂ R, —C (O) R. , —NR ₂ , —NO ₂ , —OR, a halogen atom, an aryl group or a heteroaryl group, which may further have a substituent. Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
Any _{one of} R ₁ ′ to R ₅ ′ may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl, or heteroaryl; The condensed 4- to 7-membered ring may further have a substituent.
In addition, preferred ranges for R ₁ ′ to R ₅ ′ are the same as R ^T1 to R ^T7 and R ′ in formula (E-3). Further, it is particularly preferable that A represents CR ′, and 0 to 2 of R ^T1 to R ^T4 , R ′, and R ₁ ′ to R ₅ ′ are alkyl groups or phenyl groups, and the rest are all hydrogen atoms. More preferably, 0 to 2 of R ^T1 to R ^T4 , R ′, and R ₁ ′ to R ₅ ′ are alkyl groups and the rest are all hydrogen atoms.

Another preferred embodiment of the compound represented by the general formula (E-3) is a compound represented by the following general formula (E-5).

R ^T2 to R ^T6 , A, (XY) and n _E5 in the general formula (E-5) are R ^T2 to R ^T6 , A, (XY) and n _{E3 in the} general formula (E-3). The preferred range is also the same. R ₆ ′ to R ₈ ′ are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, alkynyl group, cyano group, perfluoroalkyl group, trifluorovinyl group, —CO ₂ R, —C (O) R. , —NR ₂ , —NO ₂ , —OR, a halogen atom, an aryl group or a heteroaryl group, which may further have a substituent. Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
R ^T5 , R ^T6 , and R ₆ ′ to R ₈ ′ may be combined with each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl or It is heteroaryl, and the fused 4- to 7-membered ring may further have a substituent.
Further, preferred ranges for R ₆ ′ to R ₈ ′ are the same as R ^T1 to R ^T7 and R ′ in formula (E-3). Further, it is particularly preferable that A represents CR ′, and 0 to 2 of R ^T2 to R ^T6 , R ′, and R ₆ ′ to R ₈ ′ are alkyl groups or phenyl groups, and the rest are all hydrogen atoms. , R ^T2 to R ^T6 , R ′, and R ₆ ′ to R ₈ ′ are more preferably a case where 0 to 2 are alkyl groups and the rest are all hydrogen atoms.

When the phosphorescent material represented by the general formula (E-4) or (E-5) is used, the compound represented by the general formula (1) is preferably contained in the light emitting layer or the hole blocking layer. More preferably, it is contained in the light emitting layer.

Another preferred embodiment of the compound represented by the general formula (E-1) is a case represented by the following general formula (E-6).

In general formula (E-6), R _1a to R _1k each independently represent a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, a cyano group, a perfluoroalkyl group, a trifluorovinyl group, —CO ₂ R, —C (O) R, —NR ₂ , —NO ₂ , —OR, a halogen atom, an aryl group or a heteroaryl group, which may further have a substituent. Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
Any two of R _1a to R _1k may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is cycloalkyl, aryl, or heteroaryl; The 7-membered ring may further have a substituent.
(XY) represents a monoanionic bidentate ligand.
n _E6 represents an integer of 1 to 3.

In the general formula (E-6), preferred ranges of R _1a to R _1k are the same as those in R ^T1 to R ^T7 and R ′ in the general formula (E-3). Further, it is particularly preferred that 0 to 2 of R _1a to R _1k are alkyl groups or phenyl groups and the rest are all hydrogen atoms, and 0 to 2 of R _1a to R _1k are alkyl groups and the rest are all hydrogen More preferably, it is an atom.
The case where R _1j and R _1k are linked to form a single bond is particularly preferable.
The preferred range of (XY) and n _E6 is the same as (XY) and n _E3 in general formula (E-3).

A more preferable form of the compound represented by the general formula (E-6) is a case represented by the following general formula (E-7).

In general formula (E-7), R _1a to R _1i are each independently a hydrogen atom, alkyl group, cycloalkyl group, alkenyl group, alkynyl group, cyano group, perfluoroalkyl group, trifluorovinyl group, —CO ₂ R, —C (O) R, —NR ₂ , —NO ₂ , —OR, a halogen atom, an aryl group or a heteroaryl group, which may further have a substituent. Each R independently represents a hydrogen atom, an alkyl group, a perhaloalkyl group, an alkenyl group, an alkynyl group, a heteroalkyl group, an aryl group or a heteroaryl group.
Any one of R _1a to R _1k may be bonded to each other to form a condensed 4- to 7-membered ring, and the condensed 4- to 7-membered ring is a cycloalkyl group, an aryl group, or a heteroaryl group; The condensed 4- to 7-membered ring may further have a substituent.
(XY) represents a monoanionic bidentate ligand.
n _E7 represents an integer of 1 to 3.

In the formula (E-7), definition and preferable ranges of R _1a ~ R _1i are the same as R _1a ~ R _1i in the formula (E-6). Further, it is particularly preferable that 0 to 2 of R _1a to R _1i are alkyl groups or aryl groups and the rest are all hydrogen atoms. The definitions and preferred ranges of (XY) and n _E7 are the same as (XY) and n _E3 in general formula (E-3).

When the phosphorescent material represented by the general formula (E-6) or (E-7) is used, the compound represented by the general formula (1) is preferably contained in the light emitting layer or the hole blocking layer. .

One of preferred forms of the compound represented by the general formula (E-3) is a compound represented by the following general formula (E-8).

R ^T1 to R ^T7 in general formula (E-8) have the same ^meanings as those in general formula (E-3), and preferred ranges are also the same. R ^l1 to R ^l7 and G have the same ^{meanings as} those in the ligand (l-13), and preferred ranges thereof are also the same. R ′ represents a hydrogen atom or a substituent selected from substituent group A. R ′ is preferably a hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a perfluoroalkyl group, a dialkylamino group, a fluorine atom, an aryl group, or a heteroaryl group, more preferably a hydrogen atom, an alkyl group, A fluorine atom or an aryl group, more preferably a hydrogen atom. n _E8 represents an integer of 1 to 3, and is preferably 2 or 1.

One of preferable forms of the compound represented by the general formula (E-3) is a compound represented by the following general formula (E-9).

R ^T1 and R ^T3 to R ^T7 in general formula (E-9) have the same ^meanings as those in general formula (E-3), and preferred ranges are also the same. R ^l1 to R ^l7 and G have the same ^{meanings as} those in the ligand (l-13), and preferred ranges thereof are also the same. R ′ represents a hydrogen atom or a substituent selected from substituent group A. R ′ is preferably a hydrogen atom, an alkyl group, a cyano group, a trifluoromethyl group, a perfluoroalkyl group, a dialkylamino group, a fluorine atom, an aryl group, or a heteroaryl group, more preferably a hydrogen atom, an alkyl group, A fluorine atom or an aryl group, more preferably a hydrogen atom. n _E9 represents an integer of 1 to 3, and is preferably 2 or 1. X represents an oxygen atom or a sulfur atom.

Preferred specific examples of the compound represented by the general formula (E-1) are listed below, but are not limited thereto.

The compounds exemplified as the compound represented by the general formula (E-1) can be synthesized by the method described in JP2009-99783A, various methods described in US Pat. No. 7,279,232 and the like. After synthesis, it is preferable to purify by sublimation purification after purification by column chromatography, recrystallization or the like. By sublimation purification, not only can organic impurities be separated, but inorganic salts and residual solvents can be effectively removed.

The compound represented by the general formula (E-1) is preferably contained in the light emitting layer, but its application is not limited and may be further contained in any layer in the organic layer.

The compound represented by the general formula (E-1) in the light emitting layer is generally contained in the light emitting layer in an amount of 0.1% by mass to 50% by mass with respect to the total mass of the compound forming the light emitting layer. From the viewpoint of durability and external quantum efficiency, the content is preferably 1% by mass to 50% by mass, more preferably 2% by mass to 40% by mass, and more preferably 5% by mass to 20% by mass. Is more preferable.

A compound represented by any one of the general formulas (1) and (2) and a compound represented by any one of the general formulas (E-1) to (E-9) are used in combination in the light emitting layer. Is particularly preferred in the present invention.

The platinum (Pt) complex that can be used as the phosphorescent material is preferably a platinum (Pt) complex represented by the following general formula (C-1).

(In the formula, Q ¹ , Q ² , Q ³ and Q ⁴ each independently represent a ligand coordinated to platinum (Pt). L ¹ , L ² and L ³ are each independently a single bond or a divalent group. Represents a linking group.)

The general formula (C-1) will be described. Q ¹ , Q ² , Q ³ and Q ⁴ each independently represent a ligand coordinated to platinum (Pt). At this time, the bond between Q ¹ , Q ² , Q ³ and Q ⁴ and platinum (Pt) may be any of a covalent bond, an ionic bond, a coordinate bond, and the like. As an atom couple | bonded with platinum (Pt) in Q < ¹ >, Q < ² >, Q < ³ > and Q < ⁴ >, a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, and a phosphorus atom are preferable, Q < ¹ >, Q < ² >, Q < ³ > Of the atoms bonded to platinum (Pt) in Q ⁴ , at least one is preferably a carbon atom, more preferably two are carbon atoms, two are carbon atoms, and two are nitrogen atoms. Is particularly preferred.
Q ¹ , Q ² , Q ^3, and Q ⁴ bonded to platinum (Pt) by a carbon atom may be an anionic ligand or a neutral ligand, and the anionic ligand is a vinyl group. Ligand, aromatic hydrocarbon ring ligand (eg benzene ligand, naphthalene ligand, anthracene ligand, phenanthrene ligand, etc.), heterocyclic ligand (eg furan ligand, thiophene coordination) Pyridine ligand, pyrazine ligand, pyrimidine ligand, pyridazine ligand, triazine ligand, thiazole ligand, oxazole ligand, pyrrole ligand, imidazole ligand, pyrazole coordination Child, a triazole ligand, and a condensed ring containing them (for example, quinoline ligand, benzothiazole ligand, etc.). A carbene ligand is mentioned as a neutral ligand.

The groups represented by Q ¹ , Q ² , Q ³ and Q ⁴ may have a substituent, and as the substituent, those exemplified as the substituent group A can be appropriately applied. Moreover, substituents may be connected to each other (when Q ³ and Q ⁴ are connected, a platinum (Pt) complex of a cyclic tetradentate ligand is formed).

The group represented by Q ¹ , Q ² , Q ³ and Q ⁴ is preferably an aromatic hydrocarbon ring ligand bonded to platinum (Pt) by a carbon atom, and an aromatic bonded to platinum (Pt) by a carbon atom. Heterocyclic heterocyclic ligands, nitrogen-containing aromatic heterocyclic ligands bonded to platinum (Pt) with nitrogen atoms, acyloxy ligands, alkyloxy ligands, aryloxy ligands, heteroaryloxy ligands A silyloxy ligand, more preferably an aromatic hydrocarbon ring ligand bonded to platinum (Pt) at a carbon atom, an aromatic heterocyclic ligand bonded to platinum (Pt) at a carbon atom, nitrogen Nitrogen-containing aromatic heterocyclic ligands, acyloxy ligands, and aryloxy ligands bonded to platinum (Pt) with atoms, more preferably aromatic hydrocarbon rings bonded to platinum (Pt) with carbon atoms Ligand, carbon atom platinum (Pt) An aromatic heterocyclic ligand bonded to the nitrogen atom, a nitrogen-containing aromatic heterocyclic ligand bonded to platinum (Pt) with a nitrogen atom, and an acyloxy ligand.

L ¹ , L ² and L ³ represent a single bond or a divalent linking group. Divalent linking groups represented by L ¹ , L ² and L ³ include alkylene groups (methylene, ethylene, propylene, etc.), arylene groups (phenylene, naphthalenediyl), heteroarylene groups (pyridinediyl, thiophenediyl, etc.) ), Imino group (—NR—) (eg phenylimino group), oxy group (—O—), thio group (—S—), phosphinidene group (—PR—) (eg phenylphosphinidene group), silylene group (—SiRR′—) (dimethylsilylene group, diphenylsilylene group, etc.), or a combination thereof. Here, R and R ′ each independently include an alkyl group, an aryl group, and the like. These linking groups may further have a substituent.
From the viewpoint of stability and emission quantum yield of the complex, preferably a single bond as L ^1, L ² and L ^3, an alkylene group, an arylene group, heteroarylene group, an imino group, an oxy group, a thio group, be a silylene group More preferably a single bond, an alkylene group, an arylene group or an imino group, still more preferably a single bond, an alkylene group or an arylene group, still more preferably a single bond, a methylene group or a phenylene group, still more preferably. Single bond, disubstituted methylene group, more preferably single bond, dimethylmethylene group, diethylmethylene group, diisobutylmethylene group, dibenzylmethylene group, ethylmethylmethylene group, methylpropylmethylene group, isobutylmethylmethylene group, diphenyl Methylene group, methylphenylmethylene group, cyclohexanediyl group, cyclope An tandiyl group, a fluorenediyl group, and a fluoromethylmethylene group.
L ¹ is particularly preferably a dimethylmethylene group, a diphenylmethylene group, or a cyclohexanediyl group, and most preferably a dimethylmethylene group.
L ² and L ³ are most preferably a single bond.

Of the platinum (Pt) complexes represented by the general formula (C-1), a platinum (Pt) complex represented by the following general formula (C-2) is more preferable.

(In the formula, L ²¹ represents a single bond or a divalent linking group. A ²¹ and A ²² each independently represents a carbon atom or a nitrogen atom. Z ²¹ and Z ²² each independently represent a nitrogen-containing aromatic heterocyclic ring. Z ²³ and Z ²⁴ each independently represents a benzene ring or an aromatic heterocycle.

The general formula (C-2) will be described. L ²¹ has the same meaning as L ^{1 in} formula (C-1), and the preferred range is also the same.

A ²¹ and A ²² each independently represent a carbon atom or a nitrogen atom. Of A ^21, A ^22, Preferably, at least one is a carbon atom, it A ^21, A ²² are both carbon atoms are preferred from the standpoint of emission quantum yield stability aspects and complexes of the complex .

Z ²¹ and Z ²² each independently represent a nitrogen-containing aromatic heterocycle. Examples of the nitrogen-containing aromatic heterocycle represented by Z ²¹ and Z ²² include a pyridine ring, pyrimidine ring, pyrazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring, triazole ring, oxadiazole ring, Examples include thiadiazole rings. From the viewpoints of complex stability, emission wavelength control and emission quantum yield, the ring represented by Z ²¹ and Z ²² is preferably a pyridine ring, a pyrazine ring, an imidazole ring or a pyrazole ring, more preferably a pyridine ring. , An imidazole ring and a pyrazole ring, more preferably a pyridine ring and a pyrazole ring, and particularly preferably a pyridine ring.

Z ²³ and Z ²⁴ each independently represent a benzene ring or an aromatic heterocycle. Examples of the nitrogen-containing aromatic heterocycle represented by Z ²³ and Z ²⁴ include pyridine ring, pyrimidine ring, pyrazine ring, pyridazine ring, triazine ring, imidazole ring, pyrazole ring, oxazole ring, thiazole ring, triazole ring, oxadi Examples include an azole ring, a thiadiazole ring, a thiophene ring, and a furan ring. From the viewpoint of stability of the complex, emission wavelength control and emission quantum yield, the ring represented by Z ²³ and Z ²⁴ is preferably a benzene ring, a pyridine ring, a pyrazine ring, an imidazole ring, a pyrazole ring, or a thiophene ring. More preferred are a benzene ring, a pyridine ring and a pyrazole ring, and still more preferred are a benzene ring and a pyridine ring.

Of the platinum (Pt) complexes represented by the general formula (C-2), one of the more preferred embodiments is a platinum (Pt) complex represented by the following general formula (C-4).

(In the general formula (C-4), A ⁴⁰¹ to A ⁴¹⁴ each independently represents C—R or a nitrogen atom. R represents a hydrogen atom or a substituent. L ⁴¹ represents a single bond or a divalent linking group. To express.)

The general formula (C-4) will be described.
A ⁴⁰¹ to A ⁴¹⁴ each independently represents C—R or a nitrogen atom. R represents a hydrogen atom or a substituent.
As the substituent represented by R, those exemplified as the substituent group A can be applied.
A ⁴⁰¹ to A ⁴⁰⁶ are preferably C—R, and Rs may be connected to each other to form a ring. When A ⁴⁰¹ to A ⁴⁰⁶ are C—R, R in A ⁴⁰² and A ⁴⁰⁵ is preferably a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine atom, or a cyano group. More preferred are a hydrogen atom, an amino group, an alkoxy group, an aryloxy group and a fluorine atom, and particularly preferred are a hydrogen atom and a fluorine atom. R in A ⁴⁰¹ , A ⁴⁰³ , A ⁴⁰⁴ and A ⁴⁰⁶ is preferably a hydrogen atom, an alkyl group, an aryl group, an amino group, an alkoxy group, an aryloxy group, a fluorine atom or a cyano group, more preferably a hydrogen atom or amino Group, an alkoxy group, an aryloxy group and a fluorine atom, and particularly preferably a hydrogen atom.
L ⁴¹ has the same meaning as L ^{1 in} formula (C-1), and the preferred range is also the same.

As A ⁴⁰⁷ to A ⁴¹⁴ , in each of A ⁴⁰⁷ to A ⁴¹⁰ and A ⁴¹¹ to A ⁴¹⁴ , the number of N (nitrogen atoms) is preferably 0 to 2, and more preferably 0 to 1. In the case of shifting the emission wavelength to the short wavelength side, either A ⁴⁰⁸ or A ⁴¹² is preferably a nitrogen atom, and more preferably both A ⁴⁰⁸ and A ⁴¹² are nitrogen atoms.

Of the platinum (Pt) complexes represented by the general formula (C-2), one of the more preferred embodiments is a platinum (Pt) complex represented by the following general formula (C-5).

(In the general formula (C-5), A ⁵⁰¹ to A ⁵¹² each independently represents C—R or a nitrogen atom, R represents a hydrogen atom or a substituent, and L ⁵¹ represents a single bond or a divalent linkage. Represents a group.)

The general formula (C-5) will be described. A ⁵⁰¹ to A ⁵⁰⁶ and L ⁵¹ have the same ^{meanings as} A ⁴⁰¹ to A ⁴⁰⁶ and L ⁴¹ in formula (C-4), and preferred ranges thereof are also the same.

A ⁵⁰⁷ , A ⁵⁰⁸ and A ⁵⁰⁹ and A ⁵¹⁰ , A ⁵¹¹ and A ⁵¹² and each independently represent C—R or a nitrogen atom. R represents a hydrogen atom or a substituent. As the substituent represented by R, those exemplified as the substituent group A can be applied.

Among the platinum (Pt) complexes represented by the general formula (C-1), another more preferable embodiment is a platinum (Pt) complex represented by the following general formula (C-6).

(In the formula, L ⁶¹ represents a single bond or a divalent linking group. A ⁶¹ independently represents a carbon atom or a nitrogen atom. Z ⁶¹ and Z ⁶² each independently represent a nitrogen-containing aromatic heterocycle. Z ⁶³ independently represents a benzene ring or an aromatic heterocycle, and Y is an anionic acyclic ligand bonded to platinum (Pt).

The general formula (C-6) will be described. L ⁶¹ has the same meaning as L ^{1 in} formula (C-1), and the preferred range is also the same.

A ⁶¹ represents a carbon atom or a nitrogen atom. In view of the stability of the complex and the light emission quantum yield of the complex, A ⁶¹ is preferably a carbon atom.

Z ⁶¹ and Z ⁶² are synonymous with Z ²¹ and Z ²² in the general formula (C-2), respectively, and preferred ranges thereof are also the same. Z ⁶³ has the same meaning as Z ²³ in formula (C-2), and the preferred range is also the same.

Y is an anionic acyclic ligand that binds to platinum (Pt). An acyclic ligand is one in which atoms bonded to platinum (Pt) do not form a ring in the state of a ligand. As an atom couple | bonded with platinum (Pt) in Y, a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom are preferable, a nitrogen atom and an oxygen atom are more preferable, and an oxygen atom is the most preferable.
A vinyl ligand is mentioned as Y couple | bonded with platinum (Pt) by a carbon atom. Examples of Y bonded to platinum (Pt) with a nitrogen atom include an amino ligand and an imino ligand. Examples of Y bonded to platinum (Pt) with an oxygen atom include an alkoxy ligand, an aryloxy ligand, a heteroaryloxy ligand, an acyloxy ligand, a silyloxy ligand, a carboxyl ligand, and a phosphate group. Examples thereof include ligands and sulfonic acid ligands. Examples of Y bonded to platinum (Pt) with a sulfur atom include alkyl mercapto ligands, aryl mercapto ligands, heteroaryl mercapto ligands, and thiocarboxylic acid ligands.
The ligand represented by Y may have a substituent, and those listed as the substituent group A can be appropriately applied as the substituent. Moreover, substituents may be connected to each other.

The ligand represented by Y is preferably a ligand bonded to platinum (Pt) with an oxygen atom, and more preferably an acyloxy ligand, an alkyloxy ligand, an aryloxy ligand, a heteroaryloxy A ligand and a silyloxy ligand are preferable, and an acyloxy ligand is more preferable.

Of the platinum (Pt) complexes represented by the general formula (C-6), one of the more preferred embodiments is a platinum (Pt) complex represented by the following general formula (C-7).

(Wherein A ⁷⁰¹ to A ⁷¹⁰ each independently represents C—R or a nitrogen atom, R represents a hydrogen atom or a substituent, L ⁷¹ represents a single bond or a divalent linking group, Y represents (It is an anionic acyclic ligand that binds to platinum (Pt).)

The general formula (C-7) will be described. L ⁷¹ has the same meaning as L ^{61 in} formula (C-6), and the preferred range is also the same. A ⁷⁰¹ to A ⁷¹⁰ have the same ^{meanings as} A ⁴⁰¹ to A ⁴¹⁰ in formula (C-4), and the preferred ranges are also the same. Y has the same meaning as Y in formula (C-6), and the preferred range is also the same.

Specific examples of the platinum (Pt) complex represented by the general formula (C-1) include [0143] to [0152], [0157] to [0158], and [0162] to JP-A-2005-310733. Compounds described in [0168], compounds described in JP-A-2006-256999, [0065]-[0083], compounds described in JP-A-2006-93542, [0065]-[0090], JP-A The compounds described in [0063] to [0071] of 2007-73491, the compounds described in [0079] to [0083] of JP 2007-324309, and [0065] to [0065] of JP 2006-93542 A Compounds described in [0090], compounds described in [0055] to [0071] of JP-A-2007-96255, JP-A-2006-31379 No. [0043] - [0046] can be mentioned publications, other include platinum (Pt) complex exemplified below.

The platinum (Pt) complex compound represented by the general formula (C-1) is described in, for example, Journal of Organic Chemistry 53,786, (1988), G.A. R. Newkome et al. ), Page 789, method described in left column 53 to right column 7, line 790, method described in left column 18 to 38, method 790, method described in right column 19 to 30 and The combination, Chemische Berichte 113, 2749 (1980), H.C. Lexy et al.), Page 2752, lines 26 to 35, and the like.
For example, a ligand or a dissociated product thereof and a metal compound are mixed with a solvent (for example, a halogen solvent, an alcohol solvent, an ether solvent, an ester solvent, a ketone solvent, a nitrile solvent, an amide solvent, a sulfone solvent, In the presence of a sulfoxide solvent, water, etc., or in the absence of a solvent, in the presence of a base (inorganic and organic bases such as sodium methoxide, t-butoxypotassium, triethylamine, potassium carbonate, etc.) Or in the absence of a base, at room temperature or below, or by heating (in addition to normal heating, a method of heating with a microwave is also effective).

The content of the compound represented by the general formula (C-1) in the light emitting layer of the organic electroluminescence of the present invention is preferably 1 to 30% by mass, and preferably 3 to 25% by mass in the light emitting layer. More preferred is 5 to 20% by mass.

The type of the fluorescent material is not particularly limited. For example, benzoxazole, benzimidazole, benzothiazole, styrylbenzene, polyphenyl, diphenylbutadiene, tetraphenylbutadiene, naphthalimide, coumarin, pyran, perinone, oxa Diazole, aldazine, pyralidine, cyclopentadiene, bisstyrylanthracene, quinacridone, pyrrolopyridine, thiadiazolopyridine, cyclopentadiene, styrylamine, condensed polycyclic aromatic compounds (anthracene, phenanthrene, pyrene, perylene, fluoranthene, rubrene, chrysene) , Or pentacene), metal complexes of 8-quinolinol, various metal complexes represented by pyromethene complexes and rare earth complexes, polythiophene, polyphenylene, polyphenylene Polymeric compounds such as Nirenbiniren, organic silane, and may be derivatives of these.
Specific examples of the fluorescent material are shown below, but the present invention is not limited to these.

The content of the fluorescent light emitting material in the light emitting layer of the organic electroluminescent element of the present invention is preferably 1 to 30% by weight, more preferably 1 to 20% by weight, in the light emitting layer. More preferably.

In the present invention, from the viewpoint of preventing quenching with the compound represented by the general formula (1), the maximum emission wavelength of the light emitting material is preferably 400 to 700 nm, more preferably 500 to 700 nm. It is more preferably ˜650 nm, and most preferably 520 to 550 nm.
The maximum emission wavelength of the phosphorescent material represented by the general formula (E-3) is in the range of about 500 to 550 nm when a plurality of R ^T1 to R ^T7 and R ′ do not form a ring together. The maximum emission wavelength of the phosphorescent material represented by (E-4) or (E-5) is in the range of approximately 550 to 650 nm.

The thickness of the light emitting layer is not particularly limited, but is usually preferably 2 nm to 500 nm, and more preferably 5 nm to 200 nm, and more preferably 10 nm to 100 nm, from the viewpoint of external quantum efficiency. More preferably.

The light emitting layer in the organic electroluminescent element of the present invention may be composed only of a light emitting material, or may be a mixed layer of a host material and a light emitting material. The kind of the light emitting material may be one kind or two or more kinds. The host material is preferably a charge transport material. The host material may be one kind or two or more kinds, and examples thereof include a configuration in which an electron transporting host material and a hole transporting host material are mixed. Furthermore, the light emitting layer may contain a material that does not have charge transporting properties and does not emit light.
Further, the light emitting layer may be a single layer or a multilayer of two or more layers, and each layer may contain the same light emitting material or host material, or each layer may contain a different material. When there are a plurality of light emitting layers, each of the light emitting layers may emit light with different emission colors.

(Host material)
The host material is a compound mainly responsible for charge injection and transport in the light emitting layer, and itself is a compound that does not substantially emit light. Here, “substantially does not emit light” means that the amount of light emitted from the compound that does not substantially emit light is preferably 5% or less, more preferably 3% or less of the total amount of light emitted from the entire device. Preferably it says 1% or less.
As the host material, a compound represented by the general formula (1) can be used.

Examples of other host materials that can be used in the organic electroluminescence device of the present invention include the following compounds.
Pyrrole, indole, carbazole, azaindole, azacarbazole, triazole, oxazole, oxadiazole, pyrazole, imidazole, thiophene, benzothiophene, dibenzothiophene, furan, benzofuran, dibenzofuran, polyarylalkane, pyrazoline, pyrazolone, phenylenediamine, aryl Amine, amino-substituted chalcone, styrylanthracene, fluorenone, hydrazone, stilbene, silazane, aromatic tertiary amine compounds, styrylamine compounds, porphyrin compounds, condensed aromatic hydrocarbon compounds (anthracene, pyrene, fluorene, naphthalene, phenanthrene) , Triphenylene, etc.), polysilane compounds, poly (N-vinylcarbazole), aniline copolymers, thiopheneol , Conductive polymer oligomers such as polythiophene, organic silane, carbon film, pyridine, pyrimidine, triazine, imidazole, pyrazole, triazole, oxazole, oxadiazol, fluorenone, anthraquinodimethane, anthrone, diphenylquinone Thiopyran dioxide, carbodiimide, fluorenylidenemethane, distyrylpyrazine, fluorine-substituted aromatic compounds, heterocyclic tetracarboxylic anhydrides such as naphthaleneperylene, phthalocyanines, metal complexes of 8-quinolinol derivatives and metal phthalocyanines, Examples thereof include various metal complexes represented by metal complexes having benzoxazole or benzothiazol as a ligand, and derivatives thereof (which may have a substituent or a condensed ring).
Of these, carbazole, dibenzothiophene, dibenzofuran, arylamine, fused aromatic hydrocarbon compounds, and metal complexes are particularly preferable.

The host material that can be used in combination in the light emitting layer of the organic electroluminescent device of the present invention may be a hole transporting host material or an electron transporting host material.

In the light emitting layer, the triplet lowest excitation energy (T ₁ energy) in the film state of the host material is preferably higher than the T ₁ energy of the phosphorescent light emitting material in terms of color purity, light emission efficiency, and driving durability. It is preferable T ₁ is greater 0.1eV higher than the T ₁ of the phosphorescent material of the host material, more preferably at least 0.2eV higher, and further preferably more than 0.3eV large.
T ₁ of the a film state of the host material is a large T ₁ is obtained from the phosphorescent material to the host material for thereby quench T ₁ is less than the light emission of the phosphorescent material. Even if the T _{1 of} the host material is larger than the phosphorescent light emitting material, if the difference in T ₁ between the two is small, the reverse energy transfer from the phosphorescent light emitting material to the host material occurs in part, resulting in a decrease in efficiency and durability. Cause. Therefore, there is a demand for a host material having a sufficiently large T ₁ and high chemical stability and carrier injection / transport properties.

In addition, the content of the host compound in the light emitting layer in the organic electroluminescent device of the present invention is not particularly limited, but is 15 mass with respect to the total compound mass forming the light emitting layer from the viewpoint of light emission efficiency and driving voltage. % Or more and 95% by mass or less is preferable. When the light emitting layer contains a plurality of types of host compounds including the compound represented by the general formula (1), the compound represented by the general formula (1) is 50% by mass or more and 99% by mass or less in all the host compounds. It is preferable.

(Other layers)
The organic electroluminescent element of the present invention may have other layers other than the light emitting layer.
Other organic layers other than the light emitting layer that the organic layer may have include a hole injection layer, a hole transport layer, a block layer (hole block layer, exciton block layer, etc.), an electron transport layer, and the like. Is mentioned. Examples of the specific layer configuration include the following, but the present invention is not limited to these configurations.
Anode / hole transport layer / light emitting layer / electron transport layer / cathode,
Anode / hole transport layer / light emitting layer / block layer / electron transport layer / cathode,
Anode / hole transport layer / light emitting layer / block layer / electron transport layer / electron injection layer / cathode,
Anode / hole injection layer / hole transport layer / light emitting layer / block layer / electron transport layer / cathode,
Anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode,
Anode / hole injection layer / hole transport layer / light emitting layer / block layer / electron transport layer / electron injection layer / cathode,
Anode / hole injection layer / hole transport layer / block layer / light emitting layer / block layer / electron transport layer / electron injection layer / cathode.
The organic electroluminescent element of the present invention preferably includes (A) at least one organic layer preferably disposed between the anode and the light emitting layer. Examples of the organic layer (A) preferably disposed between the anode and the light emitting layer include a hole injection layer, a hole transport layer, and an electron block layer from the anode side.
The organic electroluminescent element of the present invention preferably includes (B) at least one organic layer preferably disposed between the cathode and the light emitting layer. Examples of the organic layer (B) preferably disposed between the cathode and the light emitting layer include an electron injection layer, an electron transport layer, and a hole blocking layer from the cathode side.
Specifically, an example of a preferred embodiment of the organic electroluminescent element of the present invention is the embodiment described in FIG. 1, and as the organic layer, a hole injection layer 4, a hole transport layer 5, In this embodiment, the light emitting layer 6, the hole blocking layer 7, and the electron transport layer 8 are laminated in this order.
Hereinafter, other layers other than the light emitting layer which may be included in the organic electroluminescent element of the present invention will be described.

(A) Organic layer preferably disposed between the anode and the light emitting layer First, (A) the organic layer preferably disposed between the anode and the light emitting layer will be described.

(A-1) Hole injection layer, hole transport layer The hole injection layer and the hole transport layer are layers having a function of receiving holes from the anode or the anode side and transporting them to the cathode side.
For the hole injection layer and the hole transport layer, the matters described in paragraph numbers [0165] to [0167] of JP-A-2008-270736 can be applied to the present invention.

The hole injection layer preferably contains an electron accepting dopant. By containing an electron-accepting dopant in the hole injection layer, hole injection properties are improved, driving voltage is lowered, and efficiency is improved. The electron-accepting dopant may be any organic material or inorganic material as long as it can extract electrons from the doped material and generate radical cations. For example, tetracyanoquinodimethane ( TCNQ), tetrafluorotetracyanoquinodimethane (F ₄ -TCNQ), molybdenum oxide and the like.

The electron-accepting dopant in the hole injection layer is preferably contained in an amount of 0.01% by mass to 50% by mass, and preferably 0.1% by mass to 40% by mass with respect to the total mass of the compound forming the hole injection layer. %, More preferably 0.2% by mass to 30% by mass.

(A-2) Electron Blocking Layer The electron blocking layer is a layer having a function of preventing electrons transported from the cathode side to the light emitting layer from passing through to the anode side. In the present invention, an electron blocking layer can be provided as an organic layer adjacent to the light emitting layer on the anode side.
As an example of the organic compound constituting the electron blocking layer, for example, those mentioned as the hole transport material described above can be applied.
The thickness of the electron blocking layer is preferably 1 nm to 500 nm, more preferably 3 nm to 100 nm, and even more preferably 5 nm to 50 nm.
The electron blocking layer may have a single layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.
The material used for the electron blocking layer is preferably higher than the T ₁ energy of the phosphorescent material in terms of color purity, luminous efficiency, and driving durability. It is preferable T ₁ is greater than 0.1eV than T ₁ of the phosphorescent material in the film state of the material used for the electron blocking layer, it is more preferably at least 0.2eV higher, and further preferably more than 0.3eV large.

(B) Organic layer preferably disposed between the cathode and the light emitting layer Next, the (B) organic layer preferably disposed between the cathode and the light emitting layer will be described.

(B-1) Electron Injection Layer, Electron Transport Layer The electron injection layer and the electron transport layer are layers having a function of receiving electrons from the cathode or the cathode side and transporting them to the anode side. The electron injection material and the electron transport material used for these layers may be a low molecular compound or a high molecular compound.
As the electron transport material, the compound represented by the general formula (1) can be used. Other electron transport materials include pyridine derivatives, quinoline derivatives, pyrimidine derivatives, pyrazine derivatives, phthalazine derivatives, phenanthroline derivatives, triazine derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, benzimidazole derivatives, imidazopyridine derivatives. , Fluorenone derivatives, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carbodiimide derivatives, fluorenylidenemethane derivatives, distyrylpyrazine derivatives, aromatic tetracarboxylic anhydrides such as naphthalene and perylene, Metal complexes of phthalocyanine derivatives, 8-quinolinol derivatives, metal phthalocyanines, benzoxazoles and benzothiazoles as ligands Various metal complexes typified by metal complexes, organosilane derivatives typified by siloles, condensed hydrocarbon compounds such as naphthalene, anthracene, phenanthrene, triphenylene, pyrene, etc., are preferred, pyridine derivatives, benzimidazole derivatives , An imidazopyridine derivative, a metal complex, or a condensed ring hydrocarbon compound is more preferable.

The thicknesses of the electron injection layer and the electron transport layer are each preferably 500 nm or less from the viewpoint of lowering the driving voltage.
The thickness of the electron transport layer is preferably 1 nm to 500 nm, more preferably 5 nm to 200 nm, and even more preferably 10 nm to 100 nm. The thickness of the electron injection layer is preferably from 0.1 nm to 200 nm, more preferably from 0.2 nm to 100 nm, and even more preferably from 0.5 nm to 50 nm.
The electron injection layer and the electron transport layer may have a single layer structure composed of one or more of the above-described materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.

The electron injection layer preferably contains an electron donating dopant. By including an electron donating dopant in the electron injection layer, the electron injection property is improved, the driving voltage is lowered, and the efficiency is improved. The electron donating dopant may be any organic material or inorganic material as long as it can give electrons to the doped material and generate radical anions. For example, tetrathiafulvalene (TTF) And dithiaimidazole compounds such as tetrathianaphthacene (TTT) and bis- [1,3 diethyl-2-methyl-1,2-dihydrobenzimidazolyl], lithium, cesium and the like.

The electron donating dopant in the electron injection layer is preferably contained in an amount of 0.01% by mass to 50% by mass, and 0.1% by mass to 40% by mass with respect to the total mass of the compound forming the electron injection layer. More preferably, the content is 0.5 to 30% by mass.

(B-2) Hole blocking layer The hole blocking layer is a layer having a function of preventing holes transported from the anode side to the light emitting layer from passing through to the cathode side. In the present invention, a hole blocking layer can be provided as an organic layer adjacent to the light emitting layer on the cathode side.
The T ₁ energy in the film state of the organic compound constituting the hole blocking layer is higher than the T ₁ energy of the light emitting material in order to prevent energy transfer of excitons generated in the light emitting layer and not to reduce the light emission efficiency. It is preferable.
As an example of the organic compound constituting the hole blocking layer, the compound represented by the general formula (1) can be used.
Examples of other organic compounds constituting the hole blocking layer other than the compound represented by the general formula (1) include aluminum (III) bis (2-methyl-8-quinolinato) 4-phenylphenolate ( Aluminum complexes such as aluminum (III) bis (2-methyl-8-quinolinato) 4-phenylphenolate (abbreviated as Balq)), triazole derivatives, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline ( Phenanthroline derivatives such as 2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline (abbreviated as BCP)) and the like.
The thickness of the hole blocking layer is preferably 1 nm to 500 nm, more preferably 3 nm to 100 nm, still more preferably 5 nm to 50 nm.
The hole blocking layer may have a single layer structure made of one or more of the materials described above, or may have a multilayer structure made of a plurality of layers having the same composition or different compositions.
The material used for the hole blocking layer is preferably higher than the T ₁ energy of the phosphorescent light emitting material in terms of color purity, light emission efficiency, and driving durability. Holes T ₁ of the at film state of the material used in the blocking layer is preferably greater 0.1eV higher than the T ₁ of the phosphorescent material, more preferably at least 0.2eV higher, and further preferably more than 0.3eV greater .

(B-3) Material particularly preferably used for the organic layer preferably disposed between the cathode and the light emitting layer The organic electroluminescent element of the present invention is preferably disposed between the (B) cathode and the light emitting layer. As a material particularly preferably used for the material of the organic layer, a compound represented by the general formula (1), a compound represented by the following general formula (P-1), and a compound represented by the following general formula (O-1) Can be mentioned.
Hereinafter, the compound represented by the general formula (O-1) and the compound represented by the general formula (P-1) will be described.

The organic electroluminescent device of the present invention preferably includes at least one organic layer between the light emitting layer and the cathode, and the organic layer contains at least one compound represented by the following general formula (O-1). It is preferable from the viewpoint of device efficiency and driving voltage. The general formula (O-1) will be described below.

(In the general formula (O1), R ^O1 represents an alkyl group, an aryl group, or each independently .A ^O1 ~ A ^O4 representing the heteroaryl group, the C-R ^A or .R ^A representing the nitrogen atom Represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, and a plurality of R ^A may be the same or different, L ^O1 represents a divalent to hexavalent linking group comprising an aryl ring or a heteroaryl ring; N ^O1 represents an integer of 2 to 6.)

R ^O1 represents an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms). It may have a substituent selected from group A. R ^O1 is preferably an aryl group or a heteroaryl group, more preferably an aryl group. A preferable substituent when the aryl group of R ^O1 has a substituent includes an alkyl group, an aryl group or a cyano group, more preferably an alkyl group or an aryl group, and still more preferably an aryl group. When the aryl group of R ^O1 has a plurality of substituents, the plurality of substituents may be bonded to each other to form a 5- or 6-membered ring. The aryl group of R ^O1 is preferably a phenyl group which may have a substituent selected from the substituent group A, more preferably a phenyl group which may be substituted with an alkyl group or an aryl group, More preferred is an unsubstituted phenyl group or 2-phenylphenyl group.

A ^O1 to A ^O4 each independently represent C—R ^A or a nitrogen atom. Of A ^O1 to A ^O4 , 0 to 2 are preferably nitrogen atoms, more preferably 0 or 1 is a nitrogen atom. Or all of A ^O1 ~ A ^O4 is C-R ^A, or A ^O1 be a nitrogen atom, is preferably A ^O2 ~ A ^O4 is C-R ^A, A ^O1 be a nitrogen atom, A ^O2 ~ More preferably, A ^O4 is C—R ^A , A ^O1 is a nitrogen atom, A ^O2 to A ^O4 are C—R ^A , and R ^A is all hydrogen atoms.

R ^A represents a hydrogen atom, an alkyl group (preferably having a carbon number of 1 to 8), an aryl group (preferably having a carbon number of 6 to 30), or a heteroaryl group (preferably having a carbon number of 4 to 12). It may have a substituent selected from the substituent group A. The plurality of R ^A may be the same or different. R ^A is preferably a hydrogen atom or an alkyl group, more preferably a hydrogen atom.

L ^O1 represents a divalent to hexavalent linking group consisting of an aryl ring (preferably having 6 to 30 carbon atoms) or a heteroaryl ring (preferably having 4 to 12 carbon atoms). L ^O1 is preferably an arylene group, heteroarylene group, aryltriyl group, or heteroaryltriyl group, more preferably a phenylene group, a biphenylene group, or a benzenetriyl group, still more preferably a biphenylene group, Or it is a benzenetriyl group. L ^O1 may have a substituent selected from the aforementioned substituent group A, and the alkyl group, aryl group, or cyano group is preferred as the substituent when it has a substituent. Specific examples of L ^O1 include the following.

n ^O1 represents an integer of 2 to 6, preferably an integer of 2 to 4, more preferably 2 or 3. n ^O1 is most preferably 3 in terms of device efficiency, and most preferably 2 in terms of device durability.
The compound represented by the general formula (O-1) is more preferably a compound represented by the following general formula (O-2).

(In the general formula (O-2), R ^O1 represents an alkyl group, an aryl group, or a heteroaryl group. R ^O2 to R ^O4 each independently represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group. A ^O1 to A ^O4 each independently represent C—R ^A or a nitrogen atom, R ^A represents a hydrogen atom, an alkyl group, an aryl group, or a heteroaryl group, and a plurality of R ^A are the same or different. May be.)

R ^O1 and A ^O1 ~ A ^O4, the general formula (O1) in the same meaning as R ^O1 and A ^O1 ~ A ^O4 of, also the same preferable ranges thereof.
R ⁰² to R ⁰⁴ are each independently a hydrogen atom, an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms). These may have a substituent selected from the aforementioned substituent group A. R ⁰² to R ⁰⁴ are preferably a hydrogen atom, an alkyl group, or an aryl group, more preferably a hydrogen atom or an aryl group, and most preferably a hydrogen atom.

The compound represented by the general formula (O-1) has a glass transition temperature (Tg) of 100 ° C. from the viewpoint of stable operation at high temperature storage, stable operation against high temperature driving, and heat generation during driving. It is preferably from ˜300 ° C., more preferably from 120 ° C. to 300 ° C., further preferably from 120 ° C. to 300 ° C., and still more preferably from 140 ° C. to 300 ° C.

Specific examples of the compound represented by the general formula (O-1) are shown below, but the present invention is not limited thereto.

The compound represented by the general formula (O-1) can be synthesized by the method described in JP-A No. 2001-335776. After synthesis, purification by column chromatography, recrystallization, reprecipitation, etc., followed by purification by sublimation is preferred. Not only can organic impurities be separated by sublimation purification, but inorganic salts, residual solvents, moisture, and the like can be effectively removed.

In the organic electroluminescent device of the present invention, the compound represented by the general formula (O-1) is preferably contained in the organic layer between the light emitting layer and the cathode, but the cathode side layer adjacent to the light emitting layer is used. It is more preferable that it is contained.
The compound represented by the general formula (O-1) is preferably contained in an amount of 70 to 100% by mass, and more preferably 85 to 100% by mass with respect to the total mass of the organic layer to be added.

The organic electroluminescent element of the present invention preferably contains at least one organic layer between the light emitting layer and the cathode, and contains at least one compound represented by the following general formula (P) in the organic layer. Is preferable from the viewpoints of element efficiency and driving voltage. Below, general formula (P) is demonstrated.

(In the general formula (P), R ^P represents an alkyl group (preferably having 1 to 8 carbon atoms), an aryl group (preferably having 6 to 30 carbon atoms), or a heteroaryl group (preferably having 4 to 12 carbon atoms). These may have a substituent selected from the aforementioned substituent group A. nP represents an integer of 1 to 10, and when R ^P is plural, they may be the same or different. At least one of R ^P is a substituent represented by the following general formulas (P-1) to (P-3).

(In the general formulas (P-1) to (P-3), R ^P1 to R ^P3 and R ′ ^P1 to R ′ ^P3 are an alkyl group (preferably having a carbon number of 1 to 8) and an aryl group (preferably having a carbon number of 6-30) or a heteroaryl group (preferably having 4 to 12 carbon atoms), which may have a substituent selected from the aforementioned substituent group A. n ^P1 and n ^P2 are 0 to Represents an integer of 4, and when R ^P1 to R ^P3 and R ′ ^P1 to R ′ ^P3 are plural, they may be the same or different, and L ^P1 to L ^{P3 each} represents a single bond, an aryl ring or a heteroaryl ring Represents one of divalent linking groups consisting of: * represents a bonding position with the anthracene ring of the general formula (P).

As R ^P , a preferred substituent other than the substituents represented by (P-1) to (P-3) is an aryl group, more preferably any one of a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group. And more preferably a naphthyl group.
R ^P1 to R ^P3 and R ′ ^P1 to R ′ ^P3 are preferably either aryl groups or heteroaryl groups, more preferably aryl groups, still more preferably phenyl groups, biphenyl groups, terphenyl groups, It is either a naphthyl group, most preferably a phenyl group.
L ^P1 to L ^P3 are preferably a single bond or a divalent linking group comprising an aryl ring, more preferably a single bond, phenylene, biphenylene, terphenylene or naphthylene, still more preferably It is either a single bond, phenylene, or naphthylene.

Specific examples of the compound represented by the general formula (P) are shown below, but the present invention is not limited thereto.

The compound represented by the general formula (P) can be synthesized by the method described in WO2003 / 060956, WO2004 / 080975, and the like. After synthesis, purification by column chromatography, recrystallization, reprecipitation, etc., followed by purification by sublimation is preferred. Not only can organic impurities be separated by sublimation purification, but inorganic salts, residual solvents, moisture, and the like can be effectively removed.

In the organic electroluminescent element of the present invention, the compound represented by the general formula (P) is preferably contained in the organic layer between the light emitting layer and the cathode, but may be contained in a layer adjacent to the cathode. More preferred.
The compound represented by the general formula (P) is preferably contained in an amount of 70 to 100% by mass, and more preferably 85 to 100% by mass with respect to the total mass of the organic layer to be added.

<Protective layer>
In the present invention, the entire organic electric field element may be protected by a protective layer.
As for the protective layer, the matters described in JP-A-2008-270736, paragraphs [0169] to [0170] can be applied to the present invention. The material for the protective layer may be inorganic or organic.

<Sealing container>
The organic electroluminescent element of the present invention may be sealed entirely using a sealing container.
Regarding the sealing container, the matters described in paragraph [0171] of JP-A-2008-270736 can be applied to the present invention.

<Driving method>
The organic electroluminescence device of the present invention emits light by applying a direct current (which may include an alternating current component as necessary) voltage (usually 2 to 15 volts) or a direct current between the anode and the cathode. Obtainable.
The driving method of the organic electroluminescence device of the present invention is described in JP-A-2-148687, JP-A-6-301355, JP-A-5-290080, JP-A-7-134558, JP-A-8-234585, and JP-A-8-2441047. The driving methods described in each publication, Japanese Patent No. 2784615, US Pat. Nos. 5,828,429 and 6,023,308 can be applied.

The external quantum efficiency of the organic electroluminescent element of the present invention is preferably 7% or more, more preferably 10% or more, and further preferably 12% or more. The value of the external quantum efficiency should be the maximum value of the external quantum efficiency when the device is driven at 20 ° C., or the value of the external quantum efficiency in the vicinity of 300 to 400 cd / m ² when the device is driven at 20 ° C. Can do.

The internal quantum efficiency of the organic electroluminescence device of the present invention is preferably 30% or more, more preferably 50% or more, and further preferably 70% or more. The internal quantum efficiency of the device is calculated by dividing the external quantum efficiency by the light extraction efficiency. In a normal organic EL element, the light extraction efficiency is about 20%. However, the shape of the substrate, the shape of the electrode, the thickness of the organic layer, the thickness of the inorganic layer, the refractive index of the organic layer, the refractive index of the inorganic layer, etc. By devising it, it is possible to increase the light extraction efficiency to 20% or more.

<Emission wavelength>
There is no restriction | limiting in the light emission wavelength of the organic electroluminescent element of this invention. For example, among the three primary colors of light, it may be used for red light emission, green light emission, or blue light emission. Among these, the organic electroluminescence device of the present invention preferably has an emission wavelength of 500 to 700 nm from the viewpoint of the lowest excited triplet (T ₁ ) energy of the compound represented by the general formula (1).
Specifically, in the organic electroluminescent device of the present invention, when the compound represented by the general formula (1) is used as the host material of the light emitting layer, the emission wavelength is preferably 500 to 700 nm, It is more preferably 550 nm, and particularly preferably 520 to 550 nm.
On the other hand, in the organic electroluminescence device of the present invention, when the compound represented by the general formula (1) is used as a charge transport material for the hole blocking layer, the emission wavelength is preferably 400 to 700 nm, It is more preferably 600 nm, and particularly preferably 450 to 550 nm.

<Use of the organic electroluminescent device of the present invention>
The organic electroluminescent element of the present invention can be suitably used for a display element, a display, a backlight, an electrophotography, an illumination light source, a recording light source, an exposure light source, a reading light source, a sign, a signboard, an interior, or optical communication. In particular, it is preferably used for a device that is driven in a region where light emission luminance is high, such as a light emitting device, a lighting device, and a display device.

[Light emitting device]
The light emitting device of the present invention includes the organic electroluminescent element of the present invention.
Next, the light emitting device of the present invention will be described with reference to FIG.
The light emitting device of the present invention uses the organic electroluminescent element.
FIG. 2 is a cross-sectional view schematically showing an example of the light emitting device of the present invention. The light emitting device 20 in FIG. 2 includes a transparent substrate (support substrate) 2, an organic electroluminescent element 10, a sealing container 16, and the like.

The organic electroluminescent device 10 is configured by sequentially laminating an anode (first electrode) 3, an organic layer 11, and a cathode (second electrode) 9 on a substrate 2. A protective layer 12 is laminated on the cathode 9, and a sealing container 16 is provided on the protective layer 12 with an adhesive layer 14 interposed therebetween. In addition, a part of each

electrode

3 and 9, a partition, an insulating layer, etc. are abbreviate | omitted.
Here, as the adhesive layer 14, a photocurable adhesive such as an epoxy resin or a thermosetting adhesive can be used, and for example, a thermosetting adhesive sheet can also be used.

The use of the light-emitting device of the present invention is not particularly limited, and for example, it can be a display device such as a television, a personal computer, a mobile phone, and electronic paper in addition to a lighting device.

[Lighting device]
The illuminating device of this invention is characterized by including the organic electroluminescent element of this invention.
Next, the illumination device of the present invention will be described with reference to FIG.
FIG. 3 is a cross-sectional view schematically showing an example of the illumination device of the present invention. As shown in FIG. 3, the illumination device 40 of the present invention includes the organic EL element 10 and the light scattering member 30 described above. More specifically, the lighting device 40 is configured such that the substrate 2 of the organic EL element 10 and the light scattering member 30 are in contact with each other.
The light scattering member 30 is not particularly limited as long as it can scatter light. In FIG. 3, the light scattering member 30 is a member in which fine particles 32 are dispersed on a transparent substrate 31. As the transparent substrate 31, for example, a glass substrate can be preferably cited. As the fine particles 32, transparent resin fine particles can be preferably exemplified. As the glass substrate and the transparent resin fine particles, known ones can be used. In such an illuminating device 40, when light emitted from the organic electroluminescent element 10 is incident on the light incident surface 30A of the scattering member 30, the incident light is scattered by the light scattering member 30, and the scattered light is emitted from the light emitting surface 30B. It is emitted as illumination light.

[Display device]
The display device of the present invention includes the organic electroluminescent element of the present invention. Examples of the display device of the present invention include a display device such as a television, a personal computer, a mobile phone, and electronic paper.

The present invention will be described more specifically with reference to the following examples. The materials, amounts used, ratios, processing details, processing procedures, and the like shown in the following examples can be changed as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention is not limited to the specific examples shown below.

1. Synthesis Example The compound represented by the general formula (1) can be synthesized by combining the methods described in JP-T 2010-535806 and other known reactions.
Synthesis Example 1 Synthesis of Compound 1

10.0 g (32.3 mmol) of 3-bromo-p-terphenyl, 12.3 g (48.5 mmol) of bis (pinacolato) diboron, 1,1′-bis (diphenylphosphino) ferrocene] palladium dichloride dichloromethane complex (1 1) 1.32 g (1.62 mmol) of (PdCl ₂ (dppf)), 9.51 g (96.9 mmol) of potassium acetate and 170 mL of dimethyl sulfoxide (DMSO) were mixed and stirred at 70 ° C. for 4 hours under a nitrogen atmosphere. did. After returning the reaction solution to room temperature, toluene and water were added to extract the organic layer. The organic layer was concentrated, purified by column chromatography (developing solvent: toluene / hexane (1: 1)), and further recrystallized from toluene / ethanol (1: 2) to obtain 7.35 g of synthetic intermediate 1. Obtained (yield 64%).
Synthesis intermediate 1 (3.52 g, 9.88 mmol), 1-bromo-3,5-diiodobenzene (2.13 g, 5.20 mmol), palladium acetate 58 mg (0.26 mmol), triphenylphosphine 273 mg (1. 04 mmol), 2.20 g (20.8 mmol) of sodium carbonate, 32 mL of 1,2-dimethoxyethane (DME), and 16 mL of water were mixed and stirred for 12 hours under a nitrogen atmosphere. The reaction solution was returned to room temperature, and the precipitated solid was filtered. This solid was heated to complete dissolution with toluene, the black component was filtered off through Celite filtration, and then the solid precipitated at room temperature was filtered to obtain 2.12 g (66%) of Synthetic Intermediate 2.
4,4,5,5-tetramethyl-2- (triphenylene-2-yl) -1,3,2-dioxaborane 1.17 g (3.30 mmol), 1.84 g (3.00 mmol) of synthetic intermediate 2 , Tris (dibenzylideneacetone) dipalladium (Pd ₂ (dba) ₃ ) 83 mg (0.090 mmol), 2-dicyclohexylphosphino-2 ′, 6′-dimethoxybiphenyl (SPhos) 148 mg (0.36 mmol), phosphoric acid 1.28 g (6.00 mmol) of potassium, 25 mL of toluene, and 12.5 mL of water were mixed and heated to reflux for 5 hours under a nitrogen atmosphere. The reaction solution was returned to room temperature, and the precipitated solid was filtered. This solid was heated to complete dissolution with toluene, the origin component was removed by silica gel column chromatography (developing solvent: toluene), and then recrystallized with toluene to obtain 1.95 g of Compound 1 (yield 85%). .
NMR data of Compound 1
¹ H NMR (400 MHz, in DMSO-d ₆ ); δ (ppm) = 8.99 (s, 1H), 8.80-8.78 (m, 2H), 8.73-8.68 (m, 3H), 8.09-7.98 (m, 6H), 7.79 (d, 6H), 7.73-7.61 (m, 16H), 7.47 (t, 4H), 7.38. -7.35 (m, 2H) ppm.

Synthesis Example 2 Synthesis of Compound 4

4- (Triphenylsilyl) phenylboronic acid 4.18 g (11.0 mmol), p-bromoiodobenzene 12.5 g (44.0 mmol), palladium acetate 74 mg (0.33 mmol), triphenylphosphine 346 mg (1.32 mmol) ), 2.33 g (22.0 mmol) of sodium carbonate, 54 mL of 1,2-dimethoxyethane (DME), and 27 mL of water were mixed and heated to reflux for 3 hours under a nitrogen atmosphere. After returning the reaction solution to room temperature, the organic layer was extracted. After the organic layer was concentrated, the origin component was removed by silica gel column chromatography (developing solvent: toluene), and further washed with hexane to obtain 4.00 g of synthetic intermediate 3 (74%).
4.00 g (8.14 mmol) of synthetic intermediate 3, 3.10 g (12.2 mmol) of bis (pinacolato) diboron, 1,1′-bis (diphenylphosphino) ferrocene] palladium dichloride dichloromethane complex (1: 1) 335 mg (0.41 mmol) of (PdCl ₂ (dppf)), 1.84 g (18.7 mmol) of potassium acetate, and 65 mL of dimethyl sulfoxide (DMSO) were mixed and stirred at 70 ° C. for 5 hours under a nitrogen atmosphere. After returning the reaction solution to room temperature, toluene and water were added, and the organic layer was extracted. After the organic layer was concentrated, it was purified by silica gel column chromatography (developing solvent: toluene / hexane (2: 3)) and further washed with methanol to obtain 2.90 g of synthetic intermediate 4 (yield 66 %).
2.69 g (5.00 mmol) of synthetic intermediate 4, 4.68 g (15.0 mmol) of 3,3′-dibromo-1,1′-biphenyl, 34 mg (0.15 mmol) of palladium acetate, 157 mg of triphenylphosphine ( 0.60 mmol), 1.06 g (10.0 mmol) of sodium carbonate, 32 mL of toluene, and 16 mL of water were mixed and heated to reflux for 12 hours under a nitrogen atmosphere. The reaction solution was returned to room temperature, the organic layer was extracted, the organic layer was concentrated, and then purified by silica gel column chromatography (developing solvent: toluene / hexane (1: 2)). Further, 1.70 g of synthetic intermediate 5 was obtained by washing with ethanol (yield 53%).
974 mg (2.75 mmol) of 4,4,5,5-tetramethyl-2- (triphenylene-2-yl) -1,3,2-dioxaborane, 1.61 g (2.50 mmol) of synthetic intermediate 5, (Dibenzylideneacetone) dipalladium (Pd ₂ (dba) ₃ ) 69 mg (0.075 mmol), 2-dicyclohexylphosphino-2 ′, 6′-dimethoxybiphenyl (SPhos) 123 mg (0.30 mmol), potassium phosphate 1 0.06 g (5.00 mmol), 20 mL of toluene and 10 mL of water were mixed and heated to reflux for 6.5 hours under a nitrogen atmosphere. After returning the reaction solution to room temperature, the organic layer was extracted. The organic layer was concentrated, the origin component was removed by silica gel column chromatography (developing solvent: toluene), recrystallized with toluene / hexane (1: 1), and further washed with acetone to obtain 1. 61 g was obtained (yield 81%).
NMR data of compound 4
¹ H NMR (400 MHz, in DMSO-d ₆ ); δ (ppm) = 9.15 (s, 1H), 9.10-9.07 (m, 1H), 8.93 (d, 1H), 8 .88-8.83 (m, 3H), 8.32 (s, 1H), 8.18-8.14 (m, 2H), 8.00 (d, 1H), 7.95 (d, 2H) ), 7.89-7.63 (m, 13H), 7.60 (d, 2H), 7.55-7.45 (m, 15H) ppm.
Compound 2, compound 3, and compounds 5 to 12 were also synthesized according to the synthesis method of compound 1 and compound 4.

2. Element fabrication / evaluation All materials used for element fabrication were subjected to sublimation purification, and it was confirmed by high performance liquid chromatography (Tosoh TSKgel ODS-100Z) that purity (254 nm absorption intensity area ratio) was 99.9% or more. .

Example 1
A glass substrate having a thickness of 0.5 mm and a 2.5 cm square ITO film (manufactured by Geomat Co., Ltd., surface resistance 10 Ω / □) is placed in a cleaning container, subjected to ultrasonic cleaning in 2-propanol, and then subjected to UV-ozone treatment for 30 minutes. Went. The following organic compound layers were sequentially deposited on the transparent anode (ITO film) by vacuum deposition.
First layer: HAT-CN: film thickness 10 nm
Second layer: NPD: film thickness 30 nm
Third layer: host material described in Table 1 and GD-1 (mass ratio 90:10): film thickness 30 nm
Fourth layer: HBL material described in Table 1: film thickness 5 nm
Fifth layer: Alq: film thickness 45 nm
On top of this, 0.1 nm of lithium fluoride and 100 nm of metallic aluminum were vapor-deposited in this order to form a cathode.
The obtained laminate is put in a glove box substituted with nitrogen gas without being exposed to the atmosphere, and a glass sealing can and an ultraviolet curable adhesive (XNR5516HV, manufactured by Nagase Ciba Co., Ltd.) are used. Then, elements 1-1 to 1-8 and comparative elements 1-1 to 1-3 were obtained. The light emitting portion is a 2 mm × 2 mm square. Table 1 shows the results of evaluating these elements from the viewpoints of relative efficiency after storage at high temperature and the highest achieved luminance by the following method.

(A) Relative efficiency after high temperature storage Using a source measure unit 2400 manufactured by Toyo Technica, a direct current voltage was applied to each element to emit light, and the luminance was measured using a luminance meter BM-8 manufactured by Topcon Corporation. The emission spectrum and emission wavelength were measured using a spectrum analyzer PMA-11 manufactured by Hamamatsu Photonics. Based on these, the external quantum efficiency (η) with a luminance of around 1000 cd / m ² was calculated by the luminance conversion method.
Furthermore, after storing each element in a 100 degreeC thermostat for 100 hours, efficiency ((eta ')) was measured by the method similar to the previous. The ratio (η ′ / η) was used as an index of heat resistance. A larger value is more preferable.

(B) Maximum Achievable Luminance The applied voltage was increased while measuring the luminance of each element, and the maximum luminance was defined as the maximum attainable luminance, and was described as a relative value.

From Table 1 above, the organic electroluminescent device of each Example using the compound represented by the general formula (1) of

Compounds

1, 2, 4, 8, 9, 11 and 12 as the host compound of the light emitting layer was It was also found that the relative efficiency after high temperature storage was good and the maximum reached brightness was high. In addition, it was found that the devices 1-6 to 1-8 using the compound represented by the general formula (1) for the host material and the hole blocking layer of the light emitting layer have higher highest reached luminance.
On the other hand, Comparative Elements 1-1 to 1-3 use Comparative Compounds 1, 2, and 4 as the host compounds of the light emitting layer, respectively, and have low relative efficiency after storage at high temperatures and low maximum brightness. all right.
Note that the emission wavelength of the organic electroluminescent device produced in Example 1 was 522 to 527 nm.

(Example 2)
Table 2 shows the results of fabricating the device in the same manner as in Example 1 except that the layer configuration was changed to the one shown below, and performing the same evaluation as in Example 1.
First layer: 2-TNATA and F ₄ -TCNQ (mass ratio 99.7: 0.3): film thickness 160 nm
Second layer: NPD: film thickness 5 nm
Third layer: HT-1: film thickness 3 nm
Fourth layer: H-1 and GD-2 (mass ratio 85:15): film thickness 30 nm
Fifth layer: HBL material described in Table 2: film thickness 10 nm
6th layer: ET-2: film thickness 20 nm

From Table 2 above, the organic electroluminescence devices of the examples using the compounds represented by the general formula (1) of the

compounds

2, 9 and 10 as the material of the hole blocking layer are all relative efficiency after high temperature storage. It was found that the maximum brightness was also high.
On the other hand, Comparative Elements 2-1 and 2-2 were obtained by using

Comparative Compounds

2 and 3, respectively, as the material of the hole blocking layer, indicating that the relative efficiency after high-temperature storage was poor and the maximum reached luminance was low. It was.
Note that the emission wavelength of the organic electroluminescent element produced in Example 2 was 503 to 507 nm.

(Example 3)
Table 3 shows the results obtained by fabricating the device in the same manner as in Example 1 except that the layer configuration is changed to the following, and performing the same evaluation as in Example 1.
First layer: CuPc: film thickness 10 nm
Second layer: NPD: film thickness 30 nm
Third layer: Host material described in Table 3 and RD-1 (mass ratio 95: 5): film thickness 30 nm
Fourth layer: ET-2: film thickness 5 nm
5th layer: ET-3: film thickness 50 nm

From Table 3 above, the organic electroluminescent elements of the Examples using the compounds represented by the general formula (1) of Compounds 1, 6, 7 and 9 as the host compounds of the light emitting layer are all relative to each other after high temperature storage. It was found that the efficiency was good and the maximum reached luminance was also high.
On the other hand, Comparative Elements 3-1 and 3-2 were obtained by using

Comparative Compounds

2 and 5 as the host material of the light emitting layer, and it was found that the relative efficiency after high temperature storage was poor and the maximum reached luminance was low.
Note that the emission wavelength of the organic electroluminescent device produced in Example 3 was 618 to 622 nm.

Example 4
Table 4 shows the results of fabricating the device in the same manner as in Example 1 except that the layer configuration was changed to the following, and performing the same evaluation as in Example 1.
First layer: TCTA: film thickness 35 nm
Second layer: HT-2: film thickness 5 nm
Third layer: BAlq and RD-2 (mass ratio 90:10): film thickness 30 nm
Fourth layer: HBL material described in Table 4: film thickness 5 nm
5th layer: ET-4: film thickness 45 nm

From Table 4 above, the organic electroluminescence devices of the Examples using the compounds represented by the general formula (1) of the compounds 3, 6 and 11 as the material of the hole blocking layer are all relative efficiency after high temperature storage. It was found that the maximum brightness was also high.
On the other hand, Comparative Elements 4-1 and 4-2 were those using Comparative Compounds 1 and 2 as the material of the hole blocking layer, and it was found that the relative efficiency after high temperature storage was poor and the maximum reached luminance was low. .
Note that the emission wavelength of the organic electroluminescent element produced in Example 4 was 628 to 631 nm.

(Example 5)
Table 5 shows the results of fabricating the device in the same manner as in Example 1 except that the layer configuration was changed to the following, and performing the same evaluation as in Example 1.
First layer: HAT-CN: film thickness 10 nm
Second layer: NPD: film thickness 115 nm
Third layer: HT-3: film thickness 5 nm
Fourth layer: H-2 and Firepic (mass ratio 90:10): film thickness 30 nm
Fifth layer: HBL material described in Table 5: film thickness 5 nm
6th layer: ET-5: film thickness 25 nm

From Table 5 above, the organic electroluminescence devices of the examples using the compounds represented by the general formula (1) of the compounds 1, 8 and 10 as the material of the hole blocking layer are all relative efficiency after high temperature storage. It was found that the maximum brightness was also high.
On the other hand, Comparative Elements 5-1 and 5-2 use

Comparative Compounds

2 and 3 as the material of the hole blocking layer, and it was found that the relative efficiency after high-temperature storage was poor and the maximum reached luminance was low. .
Note that the emission wavelength of the organic electroluminescent element produced in Example 5 was 472 to 476 nm.

(Example 6)
Table 6 shows the results obtained by fabricating the device in the same manner as in Example 1 except that the layer configuration is changed to the following, and performing the same evaluation as in Example 1.
First layer: 2-TNATA and F ₄ -TCNQ (mass ratio 99.7: 0.3): film thickness 120 nm
Second layer: NPD: film thickness 7 nm
Third layer: HT-3: film thickness 3 nm
Fourth layer: H-3 and BD-1 (mass ratio 85:15): film thickness 30 nm
Fifth layer: HBL material described in Table 6: film thickness 5 nm
Sixth layer: BAlq: film thickness 25 nm

From Table 6 above, the organic electroluminescence devices of the examples using the compounds represented by the general formula (1) of the

compounds

5, 10 and 12 as the material of the hole blocking layer are all relative efficiency after high temperature storage. It was found that the maximum brightness was also high.
On the other hand, the comparative elements 6-1 and 6-2 were prepared using the

comparative compounds

2 and 3 as the material of the hole blocking layer, and it was found that the relative efficiency after high temperature storage was poor and the maximum reached luminance was low. .
Note that the emission wavelength of the organic electroluminescent device produced in Example 6 was 457 to 460 nm.

(Example 7)
Table 7 shows the results of fabricating an element in the same manner as in Example 1 except that the layer configuration was changed to the following, and performing the same evaluation as in Example 1.
First layer: 2-TNATA and F ₄ -TCNQ (mass ratio 99.7: 0.3): film thickness 160 nm
Second layer: NPD: film thickness 5 nm
Third layer: HT-1: film thickness 3 nm
Fourth layer: H-1 and GD-3 (mass ratio 90:10): film thickness 30 nm
Fifth layer: HBL material described in Table 7: film thickness 10 nm
6th layer: ET-2: film thickness 20 nm

(Example 8)
Table 8 shows the results of fabricating the device in the same manner as in Example 1 except that the layer configuration was changed to the following, and performing the same evaluation as in Example 1.
First layer: 2-TNATA and F ₄ -TCNQ (mass ratio 99.7: 0.3): film thickness 160 nm
Second layer: NPD: film thickness 5 nm
Third layer: HT-1: film thickness 3 nm
Fourth layer: H-1 and GD-4 (mass ratio 90:10): film thickness 30 nm
Fifth layer: HBL material described in Table 8: film thickness 10 nm
6th layer: ET-2: film thickness 20 nm

Example 9
Table 9 shows the results of fabricating an element in the same manner as in Example 1 except that the layer configuration was changed to the one shown below, and performing the same evaluation as in Example 1.
First layer: 2-TNATA and F ₄ -TCNQ (mass ratio 99.7: 0.3): film thickness 160 nm
Second layer: NPD: film thickness 5 nm
Third layer: HT-1: film thickness 3 nm
Fourth layer: H-1 and GD-5 (mass ratio 90:10): film thickness 30 nm
Fifth layer: HBL material described in Table 9: film thickness 10 nm
6th layer: ET-2: film thickness 20 nm

From Tables 7 to 9 above, the organic electroluminescent elements of the examples using the compounds of the present invention as the host compound of the light emitting layer all have good relative efficiency after high temperature storage and high maximum brightness. all right.
On the other hand, the device using the comparative compound as the host compound was found to have a low relative efficiency after storage at high temperature and a low maximum luminance.

DESCRIPTION OF SYMBOLS 2 ... Substrate 3 ... Anode 4 ... Hole injection layer 5 ... Hole transport layer 6 ... Light emitting layer 7 ... Hole block layer 8 ... Electron transport layer 9 ... -Cathode 10 ... Organic electroluminescent element 11 ... Organic layer 12 ... Protective layer 14 ... Adhesive layer 16 ... Sealing container 20 ... Light emitting device 30 ... Light scattering member 31 ..Transparent substrate 30A ... light incident surface 30B ... light exit surface 32 ... fine particles 40 ... illumination device

Claims

A charge transport material comprising a compound represented by the following general formula (1).

(In the general formula (1), R 101 and R 102 each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group, and may be further substituted with these groups or amino groups. However, the aromatic ring (aromatic ring monocyclic into .R 101 and R 102 which condensed aryl structure and condensed heteroaryl structure in R 101 and R 102 are not included, ring member carbon atoms or A total of 5 or more), n 101 represents an integer of 0 to 11, n 102 represents an integer of 0 to 9, and a plurality of R 101 and R 102 are the same A A1 to A A9 each independently represent CH (the hydrogen atom of CH may be substituted with R 102 ) or a nitrogen atom.)
The charge transport material according to claim 1, wherein the compound represented by the general formula (1) is represented by the following general formula (2).

In (formula (2), each R 111 independently represent an alkyl group, an aryl group, a heteroaryl group, a fluorine atom, or a silyl group, better .R 231 ~ be substituted with these groups or amino groups R 234 independently represents an alkyl group, a fluorine atom, a silyl group or an amino group, R 235 to R 238 each independently represents an aryl group or a heteroaryl group, provided that R 111 and R 231 to R 238 are Does not include a condensed ring aryl structure or a condensed ring heteroaryl structure, and R 111 and R 231 to R 238 include a monocyclic aromatic ring (the aromatic ring is composed of a carbon atom or a nitrogen atom) A total of 3 to 6. n 111 represents an integer of 0 to 11, y31 to y33 and y35 to y37 each independently represents an integer of 0 to 4, and y34 and y38 are Represents an integer of 0 to 5. A plurality of R 111 and R 231 to R 238 may be the same or different.A B1 to A B17 are each independently CH (the hydrogen atom of CH is substituted by R 231 to R 238) Or a ring member representing a nitrogen atom and constituting a 6-membered aromatic ring.)
3. The charge transport material according to claim 2, wherein the A B3 in the general formula (2) represents CH, and a hydrogen atom of the A B3 is substituted by at least one of the R 235 .
4. The charge transport material according to claim 1, wherein n 101 in the general formula (1) is 0.
R 101 or R 102 in the general formula (1) is a fluorine atom, a fluoroalkyl group, a cycloalkyl group, a silyl group, an alkylsilyl group, an arylsilyl group, a cycloalkylene group or a substituent containing a silicon atom linking group. The charge transport material according to any one of claims 1 to 4, wherein
The charge transport material according to any one of claims 1 to 5, wherein all monocyclic aromatic rings included in the general formula (1) are 6-membered rings of a carbon atom skeleton.
The charge transport material according to any one of claims 1 to 6, wherein the compound represented by the general formula (1) comprises only a carbon atom and a hydrogen atom.
The charge transport material according to any one of claims 1 to 7, wherein the compound represented by the general formula (1) has a molecular weight of 1200 or less.
The compound represented by the general formula (1) has four monocyclic aromatic rings (the aromatic ring is a six-membered ring composed of a carbon atom or a nitrogen atom) via a single bond. Having at least one partial structure connected continuously,
The charge transport according to any one of claims 1 to 8, wherein the number of monocyclic aromatic rings continuously connected at the para position in the partial structure is 3 or less. material.
A substrate,
A pair of electrodes disposed on the substrate, including an anode and a cathode;
An organic layer disposed between the electrodes,
An organic electroluminescent device, wherein the organic layer contains a phosphorescent material and the charge transport material according to any one of claims 1 to 9.
The organic electroluminescent element according to claim 10, wherein the phosphorescent material is represented by the following general formula (E-1).

(In the general formula (E-1), Z 1 and Z 2 each independently represents a carbon atom or a nitrogen atom. A 1 represents an atomic group that forms a 5- or 6-membered heterocycle together with Z 1 and the nitrogen atom. B 1 represents an atomic group that forms a 5- or 6-membered ring with Z 2 and a carbon atom, (XY) represents a monoanionic bidentate ligand, and n E1 represents an integer of 1 to 3. Represents.)
12. The organic electroluminescent element according to claim 10, wherein the phosphorescent material represented by the general formula (E-1) is represented by the following general formula (E-2).

(In the formula (E-2), are each A E1 ~ A E8 independently nitrogen atom or,, .R E representing a carbon atom substituted with R E represents a hydrogen atom or a substituent. (X- Y) represents a monoanionic bidentate ligand, and n E2 represents an integer of 1 to 3.)
The organic electroluminescence device according to any one of claims 10 to 12, wherein the phosphorescent material represented by the general formula (E-1) has a maximum emission wavelength of 500 nm to 700 nm.
The organic layer has a light emitting layer containing the phosphorescent material and other organic layers,
The organic electroluminescent element according to any one of claims 10 to 13, wherein the light emitting layer contains a compound represented by the general formula (1).
The organic layer has a light emitting layer containing the phosphorescent material and other organic layers,
The other organic layer includes a hole blocking layer disposed between the light emitting layer and the cathode, and the hole blocking layer contains the compound represented by the general formula (1). The organic electroluminescent element according to any one of claims 10 to 14.
16. The organic electroluminescence device according to any one of 10 to 15, wherein the maximum emission wavelength is 500 nm to 550 nm.
A light-emitting device, display device, or illumination device comprising the organic electroluminescent element according to any one of claims 10 to 16.
A compound represented by the following general formula (1).

(In the general formula (1), R 101 and R 102 each independently represents an alkyl group, an aryl group, a heteroaryl group, a fluorine atom or a silyl group, and may be further substituted with these groups or amino groups. However, the aromatic ring (aromatic ring monocyclic into .R 101 and R 102 which condensed aryl structure and condensed heteroaryl structure in R 101 and R 102 are not included, ring member carbon atoms or A total of 5 or more), n 101 represents an integer of 0 to 11, n 102 represents an integer of 0 to 9, and a plurality of R 101 and R 102 are the same A A1 to A A9 each independently represent CH (the hydrogen atom of CH may be substituted with R 102 ) or a nitrogen atom.)