WO2013145923A1

WO2013145923A1 - Organic electroluminescent element

Info

Publication number: WO2013145923A1
Application number: PCT/JP2013/053767
Authority: WO
Inventors: 由美子水木; 光則伊藤; 井上　哲也; 茎子日比野; 西村　和樹
Original assignee: 出光興産株式会社
Priority date: 2012-03-30
Filing date: 2013-02-15
Publication date: 2013-10-03

Abstract

An organic electroluminescent element which is characterized by: using, as a first host, a biscarbazole derivative that has a specific structure having a cyano group; and using, as a second host, a compound that has both a carbazole derivative structure and a nitrogen-containing heteroaromatic ring. This organic electroluminescent element has a long service life.

Description

Organic electroluminescence device

The present invention relates to an organic electroluminescence element.

When a voltage is applied to an organic electroluminescence element (hereinafter also referred to as an organic EL element), holes from the anode and electrons from the cathode are injected into the light emitting layer. Then, in the light emitting layer, the injected holes and electrons are recombined to form excitons. At this time, singlet excitons and triplet excitons are generated at a ratio of 25%: 75% according to the statistical rule of electron spin. When classified according to the light emission principle, the fluorescence type uses light emitted from singlet excitons, and therefore the internal quantum efficiency of the organic EL element is said to be limited to 25%. On the other hand, in the phosphorescent type, since light emission by triplet excitons is used, it is known that the internal quantum efficiency can be increased to 100% when intersystem crossing is efficiently performed from singlet excitons.

Conventionally, in an organic EL element, an optimal element design has been made according to a light emission mechanism of a fluorescent type and a phosphorescent type. In particular, it is known that phosphorescent organic EL elements cannot obtain high-performance elements by simple diversion of fluorescent element technology because of their light emission characteristics. The reason is generally considered as follows.
First, since phosphorescence emission is emission using triplet excitons, the energy gap of the compound used for the light emitting layer must be large. This is because the value of the singlet energy of a compound (the energy difference between the lowest excited singlet state and the ground state) is usually the triplet energy of the compound (the energy between the lowest excited triplet state and the ground state). This is because it is larger than the value of the difference.
Therefore, in order to efficiently confine the triplet energy of the phosphorescent dopant material in the device, first, a host material having a triplet energy larger than the triplet energy of the phosphorescent dopant material must be used for the light emitting layer. I must. Further, when providing the electron transport layer and the hole transport layer adjacent to the light emitting layer, a compound having a triplet energy larger than that of the phosphorescent dopant material must be used for the electron transport layer and the hole transport layer. Thus, when based on the element design concept of the conventional organic EL element, it leads to using a compound having a larger energy gap for the phosphorescent organic EL element as compared with the compound used for the fluorescent organic EL element. The drive voltage of the whole organic EL element rises.

In addition, hydrocarbon compounds having high oxidation resistance and reduction resistance useful for fluorescent elements have a large energy gap due to the large spread of π electron clouds. Therefore, in the phosphorescent organic EL element, such a hydrocarbon compound is difficult to select, and an organic compound containing a hetero atom such as oxygen or nitrogen is selected. As a result, the phosphorescent organic EL element is There is a problem that the lifetime is shorter than that of a fluorescent organic EL element.

Furthermore, the fact that the exciton relaxation rate of the triplet exciton of the phosphorescent dopant material is much longer than that of the singlet exciton also greatly affects the device performance. That is, since light emitted from singlet excitons has a high relaxation rate that leads to light emission, the diffusion of excitons to the peripheral layers of the light-emitting layer (for example, a hole transport layer or an electron transport layer) hardly occurs and is efficient. Light emission is expected. On the other hand, light emission from triplet excitons is spin-forbidden and has a slow relaxation rate, so that excitons are likely to diffuse to the peripheral layer, and thermal energy deactivation occurs from other than specific phosphorescent compounds. End up. That is, control of the recombination region of electrons and holes is more important than the fluorescent organic EL element.
For the above reasons, in order to improve the performance of phosphorescent organic EL elements, material selection and element design different from those of fluorescent organic EL elements are required.

As such a phosphorescent organic EL element material, a carbazole derivative which has been conventionally known as a hole transporting material and exhibits a high triplet energy has been used as a useful phosphorescent host material.
Patent Documents 1 and 2 describe that a compound in which a nitrogen-containing heterocyclic group is introduced into a biscarbazole skeleton in which two carbazoles are linked is used as a host material in a light emitting layer of a phosphorescent organic EL element. . The compounds described in Patent Documents 1 and 2 have a molecular design that balances charge transport by introducing an electron-deficient nitrogen-containing heterocyclic group into a hole-transporting carbazole skeleton. However, in the organic EL device using the compounds described in Patent Documents 1 and 2, extending the life is a technical problem.
As an effort to extend the lifetime of organic EL elements, Patent Document 3 discloses that a longer lifetime can be obtained by mixing a plurality of host materials in the light emitting layer. Examination of combinations of various host materials to be mixed Has been made.
However, the organic EL element is desired to have a longer lifetime.

WO2011 / 132683 WO2011 / 132684 publication WO2011 / 155507

An object of the present invention is to provide a long-life organic electroluminescence element.

As a result of intensive studies by the present inventors to achieve the above object, a biscarbazole derivative having a specific structure having a cyano group is used as the first host of the light emitting layer, and the carbazole derivative structure is used as the second host of the light emitting layer. And using a compound having both a nitrogen-containing heteroaromatic ring, it has been found that the lifetime of the organic EL device can be extended, and the present invention has been achieved.

That is, the present invention provides the following inventions.
1. An organic electroluminescence device comprising at least a light emitting layer between an anode and a cathode, wherein the light emitting layer is represented by a first host material represented by the following general formula (A) and the following general formula (1): An organic electroluminescence device comprising: a second host material; and a light emitting material.

[In the formula (A),
A ¹ and A ² each independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
A ³ represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.
m represents an integer of 0 to 3.
X ¹ to X ⁸ and Y ¹ to Y ⁸ each independently represent N or CR ^a .
R ^a is independently a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, substituted or unsubstituted It represents a substituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted silyl group, a halogen atom or a cyano group. When ^a plurality of R ^a are present, the plurality of R ^a may be the same or different.
One of X ⁵ to X ⁸ and one of Y ¹ to Y ⁴ are bonded via A ³ .
Further, the formula (A) satisfies at least one of the following (i) to (v).
(I) At least one of A ¹ and A ² is an aromatic hydrocarbon group having 6 to 30 ring carbon atoms substituted with a cyano group, or a hetero ring having 5 to 30 ring atoms substituted with a cyano group. It is a cyclic group.
(Ii) At least one of X ¹ to X ⁴ and Y ⁵ to Y ⁸ is CR ^a , and at least one of R ^a in X ¹ to X ⁴ and Y ⁵ to Y ⁸ is substituted with a cyano group It is an aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a heterocyclic group having 5 to 30 ring atoms substituted with a cyano group.
(Iii) m is an integer of 1 to 3, and at least one of A ³ is substituted with a divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms substituted with a cyano group, or a cyano group And a divalent heterocyclic group having 5 to 30 ring atoms.
(Iv) At least one of X ⁵ to X ⁸ and Y ¹ to Y ⁴ is CR ^a , and at least one of R ^a in X ⁵ to X ⁸ and Y ¹ to Y ⁸ is substituted with a cyano group It is an aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a heterocyclic group having 5 to 30 ring atoms substituted with a cyano group.
(V) At least one of X ¹ to X ⁸ and Y ¹ to Y ⁸ is C—CN. ]

[In general formula (1),
Z ¹ represents a ring structure represented by the following general formula (1-1) or (1-2) condensed in a. Z ² represents a ring structure represented by the following general formula (1-1) or (1-2) condensed at b. However, at least one of Z ^{1 and} Z ² is represented by the following general formula (1-1).
M ¹ is a substituted or unsubstituted nitrogen-containing heteroaromatic ring having 5 to 30 ring atoms,
L ¹ represents a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, a ring It represents a cycloalkylene group having 5 to 30 carbon atoms formed or a group in which these are linked.
k represents 1 or 2. ]

[In the above general formula (1-1),
c represents condensation in a or b in the general formula (1).
In the above (1-2), any one of d, e and f represents condensation in a or b in the general formula (1).
In the general formulas (1-1) and (1-2),
X ¹¹ represents a sulfur atom, an oxygen atom, N—R ¹⁹ , or C (R ²⁰ ) (R ²¹ ).
R ¹¹ to R ²¹ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted ring formation. A heterocyclic group having 5 to 30 atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms Group, substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or It represents an unsubstituted aralkyl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms.
Adjacent R ¹¹ to R ²¹ may be bonded to each other to form a ring. ]
2. 2. The organic electroluminescence device according to 1 above, wherein the first host material satisfies at least one of (i) and (ii).
3. In the general formula (A), A ³ represents a substituted or unsubstituted divalent monocyclic hydrocarbon group having 6 or less ring carbon atoms, or a substituted or unsubstituted divalent monocyclic hydrocarbon group having 6 or less ring atoms. 3. The organic electroluminescence device according to 1 or 2 above, which represents a ring heterocyclic group.
4). 4. The organic electroluminescence device according to any one of 1 to 3, wherein the second host material is represented by the following general formula (2).

[In general formula (2),
Z ¹ represents a ring structure represented by the general formula (1-1) or (1-2) condensed in a. Z ² represents a ring structure represented by the general formula (1-1) or (1-2) condensed at b. However, at least one of Z ^{1 and} Z ² is represented by the general formula (1-1).
L ¹ has the same meaning as L ¹ in Formula (1).
X ¹² to X ¹⁴ are each independently a nitrogen atom, CH, or a carbon atom bonded to R ³¹ or L ^1, and at least one of X ¹² to X ¹⁴ is a nitrogen atom.
Y ¹¹ to Y ¹³ each independently represent CH or a carbon atom bonded to R ³¹ or L ¹ .
R ³¹ each independently represents a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number 3 30 to 30 alkylsilyl groups, substituted or unsubstituted arylsilyl groups having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted ring carbon atoms having 6 to 30 carbon atoms Or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms.
If R ³¹ there are a plurality, a plurality of R ³¹ may be the same or different from each other and, R ³¹ may be bonded to each other to form a ring adjacent.
k represents 1 or 2, and n represents an integer of 0 to 4.
C in the general formula (1-1) is condensed in a or b in the general formula (2);
Any one of d, e and f in the general formula (1-2) is condensed in a or b in the general formula (2). ]
5. 5. The organic electroluminescence device according to any one of 1 to 4, wherein the second host material is represented by the following general formula (3).

[Formula (3) Medium L ¹ has the same meaning as L ¹ in Formula (1).
X ¹² to X ¹⁴ are each independently a nitrogen atom, CH, or a carbon atom bonded to R ³¹ or L ^1, and at least one of X ¹² to X ¹⁴ is a nitrogen atom.
Y ¹¹ to Y ¹³ each independently represent CH or a carbon atom bonded to R ³¹ or L ¹ .
R ³¹ each independently represents a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number 3 30 to 30 alkylsilyl groups, substituted or unsubstituted arylsilyl groups having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted ring carbon atoms having 6 to 30 carbon atoms Or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms.
If R ³¹ there are a plurality, a plurality of R ³¹ may be the same or different from each other and, R ³¹ may be bonded to each other to form a ring adjacent.
n represents an integer of 0 to 4.
R ⁴¹ to R ⁴⁸ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted ring formation. A heterocyclic group having 5 to 30 atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms Group, substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or It represents an unsubstituted aralkyl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms.
Adjacent R ⁴¹ to R ⁴⁸ may be bonded to each other to form a ring. ]
6). 6. The organic electroluminescence device according to any one of 1 to 5, wherein the first host material satisfies only the item (i).
7). 7. The organic electroluminescence device according to any one of 1 to 6, wherein the second host material is represented by the following general formula (4).

[In general formula (4),
L ¹ has the same meaning as L ¹ in Formula (1).
X ¹² to X ¹⁴ are each independently a nitrogen atom, CH, or a carbon atom bonded to R ³¹ or L ^1, and at least one of X ¹² to X ¹⁴ is a nitrogen atom.
Y ¹¹ to Y ¹³ each independently represent CH or a carbon atom bonded to R ³¹ or L ¹ .
R ³¹ each independently represents a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number 3 30 to 30 alkylsilyl groups, substituted or unsubstituted arylsilyl groups having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted ring carbon atoms having 6 to 30 carbon atoms Or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms.
If R ³¹ there are a plurality, a plurality of R ³¹ may be the same or different from each other and, R ³¹ may be bonded to each other to form a ring adjacent.
n represents an integer of 0 to 4.
L ² and L ³ each independently represent a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted 2 to 5 ring atom having 2 to 30 ring atoms. A valent heterocyclic group, a cycloalkylene group having 5 to 30 ring carbon atoms, or a group in which these are connected is represented.
R ⁵¹ to R ⁵⁴ each independently represents a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. A cyclic group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted group Alkylsilyl group having 3 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted ring carbon atoms It represents a 6-30 aralkyl group or a substituted or unsubstituted aryloxy group having 6-30 ring-forming carbon atoms.
If R ⁵¹ there are a plurality, a plurality of R ⁵¹ may be the same or different, and, R ⁵¹ may be bonded to each other to form a ring adjacent.
If R ⁵² there are a plurality, a plurality of R ⁵² may be the same or different, and, R ⁵² may be bonded to each other to form a ring adjacent.
If R ⁵³ there are a plurality, a plurality of R ⁵³ may be the same or different, and, R ⁵³ may be bonded to each other to form a ring adjacent.
If R ⁵⁴ there are a plurality, the plurality of R ⁵⁴ may be the same or different from each other and, R ⁵⁴ may be bonded to each other to form a ring adjacent.
M ² represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
p and s each independently represent an integer of 0 to 4, and q and r each independently represents an integer of 0 to 3. ]
8). In Formula (A), at least one of A ¹ and A ² is substituted with a phenyl group substituted with a cyano group, a naphthyl group substituted with a cyano group, a phenanthryl group substituted with a cyano group, or a cyano group. Dibenzofuranyl group, dibenzothiophenyl group substituted with cyano group, biphenylyl group substituted with cyano group, terphenylyl group substituted with cyano group, 9,9-diphenylfluorenyl group substituted with cyano group A 9,9′-spirobi [9H-fluoren] -2-yl group substituted with a cyano group, a 9,9-dimethylfluorenyl group substituted with a cyano group, or a triphenylenyl group substituted with a cyano group 8. The organic electroluminescence device according to any one of 1 to 7 above.
9. 9. The organic electro luminescence according to any one of 1 to 8 above, wherein the luminescent material contains a phosphorescent luminescent material which is an orthometalated complex of a metal atom selected from iridium (Ir), osmium (Os) and platinum (Pt). Luminescence element.
10. 10. The organic electroluminescence device as described in 9 above, wherein the phosphorescent material has an emission peak wavelength of 490 nm to 700 nm.

According to the present invention, a long-life organic electroluminescence device can be provided.

FIG. 1 is a schematic cross-sectional view showing an example of the organic EL element of the present invention.

The organic electroluminescence device of the present invention (hereinafter sometimes abbreviated as “organic EL device”) includes at least a light emitting layer between an anode and a cathode, and the light emitting layer is represented by the following general formula (A). It contains a first host material represented, a second host material represented by the following general formula (1), and a light emitting material.

(First host material)

[In the formula (A),
A ¹ and A ² each independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
A ³ represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.
m represents an integer of 0 to 3.
X ¹ to X ⁸ and Y ¹ to Y ⁸ each independently represent N or CR ^a .
R ^a is independently a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, substituted or unsubstituted It represents a substituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted silyl group, a halogen atom or a cyano group. When ^a plurality of R ^a are present, the plurality of R ^a may be the same or different.
One of X ⁵ to X ⁸ and one of Y ¹ to Y ⁴ are bonded via A ³ .
Further, the formula (A) satisfies at least one of the following (i) to (v).
(I) At least one of A ¹ and A ² is an aromatic hydrocarbon group having 6 to 30 ring carbon atoms substituted with a cyano group, or a hetero ring having 5 to 30 ring atoms substituted with a cyano group. It is a cyclic group.
(Ii) At least one of X ¹ to X ⁴ and Y ⁵ to Y ⁸ is CR ^a , and at least one of R ^a in X ¹ to X ⁴ and Y ⁵ to Y ⁸ is substituted with a cyano group It is an aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a heterocyclic group having 5 to 30 ring atoms substituted with a cyano group.
(Iii) m is an integer of 1 to 3, and at least one of A ³ is substituted with a divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms substituted with a cyano group, or a cyano group And a divalent heterocyclic group having 5 to 30 ring atoms.
(Iv) At least one of X ⁵ to X ⁸ and Y ¹ to Y ⁴ is CR ^a , and at least one of R ^a in X ⁵ to X ⁸ and Y ¹ to Y ⁸ is substituted with a cyano group It is an aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a heterocyclic group having 5 to 30 ring atoms substituted with a cyano group.
(V) At least one of X ¹ to X ⁸ and Y ¹ to Y ⁸ is C—CN. ]
In the formula (A), an aromatic hydrocarbon group having 6 to 30 ring carbon atoms substituted with a cyano group, or a heterocyclic group having 5 to 30 ring atoms substituted with a cyano group is further represented by cyano You may have substituents other than group.
The m is preferably 0 to 2, more preferably 0 or 1. When m is 0, one of X ⁵ to X ⁸ and one of Y ¹ to Y ⁴ are bonded through a single bond.

Examples of the aromatic hydrocarbon group having 6 to 30 ring carbon atoms represented by A ¹ , A ² and R ^a include a non-condensed aromatic hydrocarbon group and a condensed aromatic hydrocarbon group, and more specifically, , Phenyl group, naphthyl group, phenanthryl group, biphenyl group, terphenyl group, quarterphenyl group, fluoranthenyl group, triphenylenyl group, phenanthrenyl group, fluorenyl group, spirofluorenyl group, 9,9-diphenylfluorenyl group 9,9′-spirobi [9H-fluoren] -2-yl group, 9,9-dimethylfluorenyl group, benzo [c] phenanthrenyl group, benzo [a] triphenylenyl group, naphtho [1,2-c] Phenanthrenyl group, naphtho [1,2-a] triphenylenyl group, dibenzo [a, c] triphenylenyl group, benzo [b] fluorante Phenyl group, naphthyl group, biphenyl group, terphenyl group, phenanthryl group, triphenylenyl group, fluorenyl group, spirobifluorenyl group, fluoranthenyl group, phenyl group, 1-naphthyl group 2-naphthyl group, biphenyl-2-yl group, biphenyl-3-yl group, biphenyl-4-yl group, phenanthren-9-yl group, phenanthren-3-yl group, phenanthren-2-yl group, triphenylene- 2-yl group, 9,9-dimethylfluoren-2-yl group, and fluoranthen-3-yl group are more preferable.
Examples of the divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms represented by A ³ include groups obtained by divalent groups described above for the aromatic hydrocarbon group having 6 to 30 ring carbon atoms. It is done.

Examples of the heterocyclic group having 5 to 30 ring atoms represented by A ¹ , A ² and R ^a include a non-condensed heterocyclic group and a condensed heterocyclic group, and more specifically, a pyrrole ring, an isoindole Ring, benzofuran ring, isobenzofuran ring, dibenzothiophene ring, isoquinoline ring, quinoxaline ring, phenanthridine ring, phenanthroline ring, pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, triazine ring, indole ring, quinoline ring, acridine ring , Pyrrolidine ring, dioxane ring, piperidine ring, morpholine ring, piperazine ring, carbazole ring, furan ring, thiophene ring, oxazole ring, oxadiazole ring, benzoxazole ring, thiazole ring, thiadiazole ring, benzothiazole ring, triazole ring , Imidazole ring, Benzimidazole ring A group formed from a pyran ring, a dibenzofuran ring, a benzo [c] dibenzofuran ring and derivatives thereof, and the like, and a group formed from a dibenzofuran ring, a carbazole ring, a dibenzothiophene ring and derivatives thereof is preferable. 2-yl group, dibenzofuran-4-yl group, 9-phenylcarbazol-3-yl group, 9-phenylcarbazol-2-yl group, dibenzothiophen-2-yl group and dibenzothiophen-4-yl group are more preferable. .
Examples of the divalent heterocyclic group having 5 to 30 ring atoms represented by A ³ include a divalent group described above for the heterocyclic group having 5 to 30 ring atoms.

Examples of the alkyl group having 1 to 30 carbon atoms represented by ^Ra include a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, 1-methylpentyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cyclooctyl group, adamantyl group, etc. Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group Cyclopentyl, cyclohexyl is preferred.

Examples of the substituted or unsubstituted silyl group represented by ^Ra include trimethylsilyl group, triethylsilyl group, tributylsilyl group, dimethylethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, Dimethylisopropylsilyl group, dimethylpropylsilyl group, dimethylbutylsilyl group, dimethyltertiarybutylsilyl group, diethylisopropylsilyl group, phenyldimethylsilyl group, diphenylmethylsilyl group, diphenyltertiarybutylsilyl group, triphenylsilyl group, etc. And a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, and a propyldimethylsilyl group are preferable.

Examples of the halogen atom represented by ^Ra include fluorine, chlorine, bromine, iodine and the like, and fluorine is preferred.
R ^a is preferably a hydrogen atom or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.

As the optional substituent in the case of “substituted or unsubstituted” and “which may have a substituent” as described above and below, a halogen atom (fluorine, chlorine, bromine, iodine), a cyano group, a carbon number of 1 An alkyl group having 20 to 20 (preferably 1 to 6), a cycloalkyl group having 3 to 20 carbon atoms (preferably 5 to 12), an alkoxy group having 1 to 20 carbon atoms (preferably 1 to 5), and 1 to 20 (preferably 1 to 5) haloalkyl group, 1 to 20 carbon atom (preferably 1 to 5) haloalkoxy group, 1 to 10 carbon atom (preferably 1 to 5) alkylsilyl group, ring-forming carbon number Aromatic hydrocarbon group having 6 to 30 (preferably 6 to 18), aryloxy group having 6 to 30 ring carbon atoms (preferably 6 to 18), aryl having 6 to 30 carbon atoms (preferably 6 to 18 carbon atoms) Silyl group, 7-30 carbon atoms Preferably an aralkyl group having 7 to 20), and ring atoms 5 to 30 (preferably include 5 to 18) heteroaryl group.
Specific examples of the alkyl group having 1 to 20 carbon atoms used as the optional substituent include a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t -Butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n -Tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, 1-methylpentyl group and the like.
Specific examples of the cycloalkyl group having 3 to 20 carbon atoms used as the optional substituent include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cyclooctyl group, adamantyl group and the like.
Specific examples of the alkoxy group having 1 to 20 carbon atoms used as the optional substituent include groups in which the alkyl moiety is the alkyl group.
Specific examples of the haloalkyl group having 1 to 20 carbon atoms used as the optional substituent include groups in which part or all of the hydrogen atoms of the alkyl group are substituted with halogen atoms.
Specific examples of the haloalkoxy group having 1 to 20 carbon atoms used as the optional substituent include groups in which part or all of the above-described alkoxy groups are substituted with halogen atoms.
Specific examples of the alkylsilyl group having 1 to 10 carbon atoms used as the optional substituent include trimethylsilyl group, triethylsilyl group, tributylsilyl group, dimethylethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group. Propyldimethylsilyl group, dimethylisopropylsilyl group, dimethylpropylsilyl group, dimethylbutylsilyl group, dimethyltertiarybutylsilyl group, diethylisopropylsilyl group and the like.

Specific examples of the aromatic hydrocarbon group having ring carbon atoms of 6 to 30 for use as the optional substituents may be the same as those aromatic hydrocarbon group indicated by the A ^1, A ² and R ^a.
Specific examples of the aryloxy group having 6 to 30 ring carbon atoms used as the optional substituent include groups in which the aryl moiety is the aromatic hydrocarbon group.
Specific examples of the arylsilyl group having 6 to 30 carbon atoms used as the optional substituent include a phenyldimethylsilyl group, a diphenylmethylsilyl group, a diphenyl tertiary butylsilyl group, and a triphenylsilyl group.
Specific examples of the aralkyl group having 7 to 30 carbon atoms used as the optional substituent include benzyl group, 2-phenylpropan-2-yl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenyl. Isopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α- Naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, 2-β-naphthylisopropyl group, 1-pyrrolylmethyl group, 2- ( 1-pyrrolyl) ethyl group, p-methylbenzyl group, m-methylbenzyl group, o-methylbenzyl group, p-chlorobenzyl group, m-chloro Benzyl group, o-chlorobenzyl group, p-bromobenzyl group, m-bromobenzyl group, o-bromobenzyl group, p-iodobenzyl group, m-iodobenzyl group, o-iodobenzyl group, p-hydroxybenzyl group M-hydroxybenzyl group, o-hydroxybenzyl group, p-aminobenzyl group, m-aminobenzyl group, o-aminobenzyl group, p-nitrobenzyl group, m-nitrobenzyl group, o-nitrobenzyl group, p -Cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzyl group, 1-hydroxy-2-phenylisopropyl group, 1-chloro-2-phenylisopropyl group and the like.
Specific examples of the heteroaryl group having 5 to 30 ring atoms used as the optional substituent include the same heterocyclic groups as those represented by A ¹ , A ² and R ^a .

The optional substituent is preferably a fluorine atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a heteroaryl group having 5 to 30 ring atoms. , Fluorine atom, phenyl group, naphthyl group, biphenyl group, terphenyl group, phenanthryl group, triphenylenyl group, fluorenyl group, spirobifluorenyl group, fluoranthenyl group, dibenzofuran ring, carbazole ring, dibenzothiophene ring and these A group formed from a derivative, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, cyclopentyl group, and cyclohexyl group are more preferable.
The above arbitrary substituents may further have a substituent, and specific examples thereof are the same as the above arbitrary substituents.
In the present specification, “carbon number ab” in the expression “substituted or unsubstituted X group having carbon number ab” represents the number of carbons when X group is unsubstituted. The carbon number of the substituent when the X group is substituted is not included.
In the present invention, the hydrogen atom includes isotopes having different numbers of neutrons, that is, light hydrogen (protium), deuterium (triuterium), and tritium.

In the first host material represented by the above formula (A), groups represented by the following formulas (a) and (b) are linked via — (A ³ ) _m —, and the bonding position thereof is as described above. Any one of X ⁵ to X ⁸ and any one of Y ¹ to Y ⁴ . Specifically, X ^6- (A ³ ) _m -Y ³ , X ^6- (A ³ ) _m -Y ² , X ^6- (A ³ ) _m -Y ⁴ , X ^6- (A ³ ) _m- ^{^{Y 1, X 7 - (A}} 3) m -Y 3, X 5 - (A 3) m -Y 3, X 8 - (A 3) m -Y 3, X 7 - (A 3) m -Y 2 ^{^{, X 7 - (A 3)}} m -Y 4, X 7 - (A 3) m -Y 1, X 5 - (A 3) m -Y 2, X 8 - (A 3) m -Y 2, X ^{^{_{8 - (A 3) m -Y}}} 4, X 8 - (A 3) m -Y 1, X 5 - (A 3) m -Y 1, X 5 - (A 3) m -Y 4 and the like.

In the first host material represented by the above formula (A), the groups represented by the above formulas (a) and (b) are X ^6- (A ³ ) _m -Y ³ , X ^6- (A ³ ). _{^{^{m -Y 2, X 7 - (}}} a 3) is preferably attached at either the binding position of _m -Y ^3. That is, a compound represented by any one of the following formulas (II), (III), and (IV) is more preferable.

(In the formulas (II) to (IV), X ¹ to X ⁸ , Y ¹ to Y ⁸ , A ¹ to A ³ and m are X ¹ to X ⁸ and Y ¹ to Y in the formula (A), respectively. ⁸ , the same as A ¹ to A ³ and m. Furthermore, the formulas (II), (III), and (IV) are the same as the conditions (i) to (v) in the formula (A). Meet)

The first host material represented by the above formula (A) satisfies at least one of the above (i) to (v). That is, a cyano group is introduced into a biscarbazole derivative to which groups represented by the above formulas (a) and (b) are linked.
The first host material has improved hole resistance by introducing an electron injection / transport cyano group. Therefore, the organic EL device of the present invention containing the first host material having a cyano group has an effect of extending the life as compared with the conventional organic EL device using a host material having no cyano group.

A ³ in the general formula (A) is a single bond, a substituted or unsubstituted divalent monocyclic hydrocarbon group having 6 or less ring carbon atoms, or a substituted or unsubstituted divalent hydrocarbon group having 6 or less ring atoms. It is preferable to represent the monocyclic heterocyclic group.
Examples of the monocyclic hydrocarbon group having 6 or less ring carbon atoms represented by A ³ include a phenylene group, a cyclopentenylene group, a cyclopentadienylene group, a cyclohexylene group, a cyclopentylene group, and the like. A phenylene group is preferred.
Examples of the monocyclic heterocyclic group having 6 or less ring atoms represented by A ³ include a pyrrolylene group, a pyrazinylene group, a pyridinylene group, a furylene group, and a thiophenylene group.

In the general formulas (A), (II), (III) and (IV), m is 0 and one of X ⁵ to X ⁸ and one of Y ¹ to Y ⁴ are bonded via a single bond. Or A ³ is preferably a substituted or unsubstituted monocyclic hydrocarbon group having 6 or less ring-forming carbon atoms, or a substituted or unsubstituted monocyclic heterocyclic group having 6 or less ring-forming atoms. In this case, since the twist of the ring represented by the above formulas (a) and (b) (for example, carbazole ring) is reduced and the conjugation of π electrons is easily maintained, HOMO (the highest occupied molecular orbital) is the entire carbazole skeleton. The hole injection / transport property of the carbazole skeleton is maintained. In particular, m is 0 and one of X ⁵ to X ⁸ and one of Y ¹ to Y ⁴ are bonded via a single bond, or A ³ is a substituted or unsubstituted phenylene group. Is preferred.

The first host material preferably satisfies at least one of the following (i) and the following (ii).
(I) an aromatic hydrocarbon group having 6 to 30 ring carbon atoms substituted with at least one of A ¹ and A ^{2 with} a cyano group, or a heterocycle having 5 to 30 ring atoms substituted with a cyano group; It is a cyclic group.
(Ii) at least one of X ¹ ~ X ⁴ and Y ⁵ ~ Y ⁸ is CR ^a, at least one of R ^a in the X ¹ ~ X ⁴ and Y ⁵ ~ Y ⁸ is substituted with a cyano group ring An aromatic hydrocarbon group having 6 to 30 carbon atoms or a heterocyclic group having 5 to 30 ring atoms substituted with a cyano group.
That is, the first host material preferably corresponds to one of the following (1) to (3).
(1) The above (i) is satisfied, and the above (ii) to (v) are not satisfied.
(2) The above (ii) is satisfied, and the above (i) and (iii) to (v) are not satisfied.
(3) Both the above (i) and (ii) are satisfied, and the above (iii) to (v) are not satisfied.

The first host material satisfying the above (i) and / or (ii) has a cyano group on the terminal side of the central skeleton with respect to the central skeleton having the group represented by the above formulas (a) and (b). It is a structure in which a heterocyclic group having an aromatic hydrocarbon group or a cyano group is introduced.
The central skeleton having a group represented by the above formulas (a) and (b) functions as a hole injection / transport unit, and an aromatic hydrocarbon group having a cyano group or a heterocyclic group having a cyano group is Functions as an electron injection / transport unit. In the first host material satisfying the above (i) or (ii), a group having a cyano group functioning as an electron injecting / transporting unit is introduced outside the central skeleton. While maintaining the spread of the electron cloud of the occupied molecular orbital) and maintaining good hole injection / transport properties, it also has the function of electron injection / transport properties by the group having a cyano group. Thereby, since the 1st host material which satisfy | fills said (i) or (ii) becomes favorable in the carrier balance in a molecule | numerator, when using for an organic EL element, the outstanding luminous efficiency is realizable.
Therefore, the organic EL device of the present invention including a light emitting layer containing a first host material satisfying at least one of the above (i) and (ii) and a second host material represented by the formula (1). In addition to the effect of extending the lifetime, the luminous efficiency of the organic EL element is improved.

When the first host material satisfies the condition (i), at least one of A ¹ and A ² is substituted with a phenyl group substituted with a cyano group, a naphthyl group substituted with a cyano group, or a cyano group Substituted phenanthryl group, dibenzofuranyl group substituted with cyano group, dibenzothiophenyl group substituted with cyano group, biphenyl group substituted with cyano group, terphenyl group substituted with cyano group, substituted with cyano group 9,9-diphenylfluorenyl group, 9,9′-spirobi [9H-fluoren] -2-yl group substituted with a cyano group, 9,9′-dimethylfluorenyl substituted with a cyano group Or a triphenylenyl group substituted with a cyano group, preferably a 3′-cyanobiphenyl-2-yl group, a 3′-cyanobiphenyl-3-yl group, or a 3′-sia group. Biphenyl-4-yl group, 4′-cyanobiphenyl-3-yl group, 4′-cyanobiphenyl-4-yl group, 4′-cyanobiphenyl-2-yl group, 6-cyanonaphthalen-2-yl group, 4-cyanonaphthalen-1-yl group, 7-cyanonaphthalen-2-yl group, 8-cyanodibenzofuran-2-yl group, 6-cyanodibenzofuran-4-yl group, 8-cyanodibenzothiophen-2-yl group 6-cyanodibenzothiophen-4-yl group, 7-cyano-9-phenylcarbazol-2-yl group, 6-cyano-9-phenylcarbazol-3-yl group, 7-cyano-9,9-dimethylfluorene A -2-yl group and a 7-cyanotriphenylene-2-yl group are more preferable.
In the first host material, A ¹ is preferably substituted with a cyano group, and A ² is preferably not substituted with a cyano group. Furthermore, in this case, it is more preferable that the first host material does not satisfy the condition (ii).

The first host material, if the condition is satisfied in the (ii), at least one of X ¹ ~ X ⁴ and Y ⁵ ~ Y ⁸ is CR ^a, X ¹ ~ X ⁴ and Y ⁵ ~ Y ⁸ At least one of R ^a is a phenyl group substituted with a cyano group, a naphthyl group substituted with a cyano group, a phenanthryl group substituted with a cyano group, a dibenzofuranyl group substituted with a cyano group, or a cyano group Substituted dibenzothiophenyl group, biphenyl group substituted with cyano group, terphenyl group substituted with cyano group, 9,9-diphenylfluorenyl group substituted with cyano group, 9 substituted with cyano group , 9′-spirobi [9H-fluoren] -2-yl group, 9,9′-dimethylfluorenyl group substituted with cyano group, or triphenylenyl group substituted with cyano group 3'-cyanobiphenyl-2-yl group, 3'-cyanobiphenyl-3-yl group, 3'-cyanobiphenyl-4-yl group, 4'-cyanobiphenyl-3-yl group, 4'-cyanobiphenyl- 4-yl group, 4′-cyanobiphenyl-2-yl group, 6-cyanonaphthalen-2-yl group, 4-cyanonaphthalen-1-yl group, 7-cyanonaphthalen-2-yl group, 8-cyanodibenzofuran -2-yl group, 6-cyanodibenzofuran-4-yl group, 8-cyanodibenzothiophen-2-yl group, 6-cyanodibenzothiophen-4-yl group, 7-cyano-9-phenylcarbazol-2-yl A 6-cyano-9-phenylcarbazol-3-yl group, a 7-cyano-9,9-dimethylfluoren-2-yl group, and a 7-cyanotriphenylene-2-yl group. preferable.
Furthermore, when the first host material satisfies the condition (ii), it is more preferable that the condition (i) is not satisfied.

In the formulas (A) and (II) to (IV), the A ¹ and the A ² are preferably different from each other. Among them, it is more preferable that the group A ¹ is substituted with a cyano group and the group A ² is not substituted with a cyano group. That is, the first host material preferably has an asymmetric structure, and the first host material has good crystallinity and non-crystallinity due to such a structure. Therefore, since the organic EL element using the first host material has excellent film quality, for example, high performance can be achieved in organic EL characteristics such as current efficiency.

The method for producing the first host material is not particularly limited and may be produced by a known method. For example, it is described in Tetrahedron 40 (1984) 1435-1456 for carbazole derivatives and aromatic halogenated compounds. It can be produced by a coupling reaction using a copper catalyst or a palladium catalyst described in Journal of American Chemical Society 123 (2001) 7727-7729.

Hereinafter, specific examples of the first host material will be described, but the compound of the present invention is not limited to the following compounds.

(Second host material)
The second host material contained in the light emitting layer of the organic EL device of the present embodiment is a compound represented by the following general formula (1). By combining the first host material represented by the general formula (A) and the second host material represented by the following general formula (1) in the light emitting layer, the life of the organic EL element is extended. be able to.

[In the above general formula (1-1),
c represents condensation in a or b in the general formula (1).
In the general formula (1-2),
Any one of d, e and f represents condensation in a or b in the general formula (1).
In the general formulas (1-1) and (1-2),
X ¹¹ represents a sulfur atom, an oxygen atom, N—R ¹⁹ , or C (R ²⁰ ) (R ²¹ ).
R ¹¹ to R ²¹ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted ring formation. A heterocyclic group having 5 to 30 atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms Group, substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or It represents an unsubstituted aralkyl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms.
Adjacent R ¹¹ to R ²¹ may be bonded to each other to form a ring. ]

The “nitrogen-containing heteroaromatic ring” represented by M ¹ in the general formula (1) includes an azine ring.
Examples of the nitrogen-containing heteroaromatic ring represented by M ¹ in the general formula (1) include pyridine, pyrimidine, pyrazine, triazine, aziridine, azaindolizine, indolizine, imidazole, indole, isoindole, indazole, purine, Examples include pteridine, β-carboline, naphthyridine, quinoxaline, terpyridine, bipyridine, acridine, phenanthroline, phenazine, and imidazopyridine. In particular, pyridine, pyrimidine, and triazine are preferable, and represented by the following general formula (2) Those are also preferred.

[In general formula (2),
Z ¹ represents a ring structure represented by the general formula (1-1) or (1-2) condensed in a. Z ² represents a ring structure represented by the general formula (1-1) or (1-2) condensed at b. However, at least one of Z ^{1 and} Z ² is represented by the general formula (1-1).
L ¹ has the same meaning as L ¹ in Formula (1).
X ¹² to X ¹⁴ are each independently a nitrogen atom, CH, or a carbon atom bonded to R ³¹ or L ^1, and at least one of X ¹² to X ¹⁴ is a nitrogen atom.
Y ¹¹ to Y ¹³ each independently represent CH or a carbon atom bonded to R ³¹ or L ¹ .
R ³¹ each independently represents a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number 3 30 to 30 alkylsilyl groups, substituted or unsubstituted arylsilyl groups having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted ring carbon atoms having 6 to 30 carbon atoms Or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms.
If R ³¹ there are a plurality, a plurality of R ³¹ may be the same or different from each other and, R ³¹ may be bonded to each other to form a ring adjacent.
k represents 1 or 2, and n represents an integer of 0 to 4.
C in the general formula (1-1) is condensed in a or b in the general formula (2);
Any one of d, e and f in the general formula (1-2) is condensed in a or b in the general formula (2). ]

Here, examples of the compound in which the general formulas (1-1) and (2-2) are condensed in a and b in the general formula (2) include those represented by the following general formula.

The compound represented by the general formulas (1) and (2) is more preferably represented by the following general formula (3), and particularly preferably represented by the following general formula (4).

[Formula (3) Medium L ¹ has the same meaning as L ¹ in Formula (1).
X ¹² to X ¹⁴ are each independently a nitrogen atom, CH, or a carbon atom bonded to R ³¹ or L ^1, and at least one of X ¹² to X ¹⁴ is a nitrogen atom.
Y ¹¹ to Y ¹³ each independently represent CH or a carbon atom bonded to R ³¹ or L ¹ .
R ³¹ each independently represents a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number 3 30 to 30 alkylsilyl groups, substituted or unsubstituted arylsilyl groups having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted ring carbon atoms having 6 to 30 carbon atoms Or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms.
If R ³¹ there are a plurality, a plurality of R ³¹ may be the same or different from each other and, R ³¹ may be bonded to each other to form a ring adjacent.
n represents an integer of 0 to 4.
R ⁴¹ to R ⁴⁸ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted ring formation. A heterocyclic group having 5 to 30 atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms Group, substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or It represents an unsubstituted aralkyl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms.
Adjacent R ⁴¹ to R ⁴⁸ may be bonded to each other to form a ring. ]

[In general formula (4),
L ¹ has the same meaning as L ¹ in Formula (1).
X ¹² to X ¹⁴ are each independently a nitrogen atom, CH, or a carbon atom bonded to R ³¹ or L ^1, and at least one of X ¹² to X ¹⁴ is a nitrogen atom.
Y ¹¹ to Y ¹³ each independently represent CH or a carbon atom bonded to R ³¹ or L ¹ .
R ³¹ each independently represents a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number 3 30 to 30 alkylsilyl groups, substituted or unsubstituted arylsilyl groups having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted ring carbon atoms having 6 to 30 carbon atoms Or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms.
Further, adjacent R ³¹ may be bonded to each other to form a ring.
n represents an integer of 0 to 4.
L ² and L ³ each independently represent a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted 2 to 5 ring atom having 2 to 30 ring atoms. A valent heterocyclic group, a cycloalkylene group having 5 to 30 ring carbon atoms, or a group in which these are connected is represented.
R ⁵¹ to R ⁵⁴ each independently represents a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. A cyclic group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted group Alkylsilyl group having 3 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted ring carbon atoms It represents a 6-30 aralkyl group or a substituted or unsubstituted aryloxy group having 6-30 ring-forming carbon atoms.
If R ⁵¹ there are a plurality, a plurality of R ⁵¹ may be the same or different, and, R ⁵¹ may be bonded to each other to form a ring adjacent.
If R ⁵² there are a plurality, a plurality of R ⁵² may be the same or different, and, R ⁵² may be bonded to each other to form a ring adjacent.
If R ⁵³ there are a plurality, a plurality of R ⁵³ may be the same or different, and, R ⁵³ may be bonded to each other to form a ring adjacent.
If R ⁵⁴ there are a plurality, the plurality of R ⁵⁴ may be the same or different from each other and, R ⁵⁴ may be bonded to each other to form a ring adjacent.
M ² represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
p and s each independently represent an integer of 0 to 4, and q and r each independently represents an integer of 0 to 3. ]

In the general formulas (1) to (4), (1-1) and (1-2), each group represented by R ¹¹ to R ²¹ , R ³¹ , R ⁴¹ to R ⁴⁸ and R ⁵¹ to R ⁵⁴ Is a group described in the compound represented by the general formula (A).
A divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a divalent heterocyclic ring having 5 to 30 ring atoms represented by L ¹ to L ³ in the general formulas (1) to (4). Examples of the group include a group corresponding to the divalent group described for the compound represented by the general formula (A).

Examples of the compound represented by any one of the above general formulas (1) to (4) include the following. In addition, in the following structural formulas, a bond having no chemical formula (CN, benzene ring, or the like) at its end represents a methyl group.

(Organic EL device)
The organic EL device of the present invention may have a hole transport layer, a light emitting layer, a space layer, a barrier layer, and the like, and these include the same compounds as the first host material and the second host material described above. You may go out.
Examples of the light emitting material contained in the light emitting layer include a fluorescent light emitting material and a phosphorescent light emitting material, and a phosphorescent light emitting material is preferable.

The organic EL element of the present invention may be a fluorescent or phosphorescent monochromatic light emitting element, a fluorescent / phosphorescent hybrid white light emitting element, or a simple type having a single light emitting unit. A tandem type having a plurality of light emitting units may be used, and among them, a phosphorescent type is preferable. Here, the “light emitting unit” refers to a minimum unit that includes one or more organic layers, one of which is a light emitting layer, and can emit light by recombination of injected holes and electrons.

Accordingly, typical element configurations of simple organic EL elements include the following element configurations.
(1) Anode / light emitting unit / cathode The above light emitting unit may be a laminated type having a plurality of phosphorescent light emitting layers and fluorescent light emitting layers. In that case, the light emitting unit is generated by a phosphorescent light emitting layer between the light emitting layers. In order to prevent the excitons from diffusing into the fluorescent light emitting layer, a space layer may be provided. A typical layer structure of the light emitting unit is shown below.
(A) Hole transport layer / light emitting layer (/ electron transport layer)
(B) Hole transport layer / first phosphorescent light emitting layer / second phosphorescent light emitting layer (/ electron transport layer)
(C) Hole transport layer / phosphorescent layer / space layer / fluorescent layer (/ electron transport layer)
(D) Hole transport layer / first phosphorescent light emitting layer / second phosphorescent light emitting layer / space layer / fluorescent light emitting layer (/ electron transport layer)
(E) Hole transport layer / first phosphorescent light emitting layer / space layer / second phosphorescent light emitting layer / space layer / fluorescent light emitting layer (/ electron transport layer)
(F) Hole transport layer / phosphorescent layer / space layer / first fluorescent layer / second fluorescent layer (/ electron transport layer)
(G) Hole transport layer / electron barrier layer / light emitting layer (/ electron transport layer)
(H) Hole transport layer / light emitting layer / hole barrier layer (/ electron transport layer)
(I) Hole transport layer / fluorescent light emitting layer / triplet barrier layer (/ electron transport layer)

Each phosphorescent or fluorescent light-emitting layer may have a different emission color. Specifically, in the laminated light emitting layer (d), hole transport layer / first phosphorescent light emitting layer (red light emitting) / second phosphorescent light emitting layer (green light emitting) / space layer / fluorescent light emitting layer (blue light emitting) / Examples include a layer configuration such as an electron transport layer.
An electron barrier layer may be appropriately provided between each light emitting layer and the hole transport layer or space layer. Further, a hole blocking layer may be appropriately provided between each light emitting layer and the electron transport layer. By providing an electron barrier layer or a hole barrier layer, electrons or holes can be confined in the light emitting layer, the recombination probability of charges in the light emitting layer can be increased, and the light emission efficiency can be improved.

The following element structure can be mentioned as a typical element structure of a tandem type organic EL element.
(2) Anode / first light emitting unit / intermediate layer / second light emitting unit / cathode Here, as the first light emitting unit and the second light emitting unit, for example, the same light emitting unit as that described above is selected independently. can do.
The intermediate layer is generally called an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron extraction layer, a connection layer, or an intermediate insulating layer, and has electrons in the first light emitting unit and holes in the second light emitting unit. A known material structure to be supplied can be used.

FIG. 1 shows a schematic configuration of an example of the organic EL element of the present invention. The organic EL element 1 includes a substrate 2, an anode 3, a cathode 4, and a light emitting unit 10 disposed between the anode 3 and the cathode 4. The light emitting unit 10 includes a light emitting layer 5 including at least one layer including the first host material, the second host material, and the light emitting material. A hole injection / transport layer 6 or the like may be formed between the light emitting layer 5 and the anode 3, and an electron injection / transport layer 7 or the like may be formed between the light emitting layer 5 and the cathode 4. Further, an electron barrier layer may be provided on the anode 3 side of the light emitting layer 5, and a hole barrier layer may be provided on the cathode 4 side of the light emitting layer 5. Thereby, electrons and holes can be confined in the light emitting layer 5, and the exciton generation probability in the light emitting layer 5 can be increased.

In this specification, a host combined with a fluorescent dopant is referred to as a fluorescent host, and a host combined with a phosphorescent dopant is referred to as a phosphorescent host. The fluorescent host and the phosphorescent host are not distinguished only by the molecular structure. That is, the phosphorescent host means a material constituting a phosphorescent light emitting layer containing a phosphorescent dopant, and does not mean that it cannot be used as a material constituting a fluorescent light emitting layer. The same applies to the fluorescent host.

(substrate)
The organic EL element of the present invention is produced on a translucent substrate. The light-transmitting substrate is a substrate that supports the organic EL element, and is preferably a smooth substrate having a light transmittance in the visible region of 400 nm to 700 nm of 50% or more. Specifically, a glass plate, a polymer plate, etc. are mentioned. Examples of the glass plate include those using soda lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, quartz and the like as raw materials. Examples of the polymer plate include those using polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, polysulfone and the like as raw materials.

(anode)
The anode of the organic EL element plays a role of injecting holes into the hole transport layer or the light emitting layer, and it is effective to use a material having a work function of 4.5 eV or more. Specific examples of the anode material include indium tin oxide alloy (ITO), tin oxide (NESA), indium zinc oxide, gold, silver, platinum, copper, and the like. The anode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering. When light emitted from the light emitting layer is extracted from the anode, it is preferable that the transmittance of light in the visible region of the anode is greater than 10%. The sheet resistance of the anode is preferably several hundred Ω / □ or less. The film thickness of the anode depends on the material, but is usually selected in the range of 10 nm to 1 μm, preferably 10 nm to 200 nm.

(cathode)
The cathode plays a role of injecting electrons into the electron injection layer, the electron transport layer or the light emitting layer, and is preferably formed of a material having a small work function. The cathode material is not particularly limited, and specifically, indium, aluminum, magnesium, magnesium-indium alloy, magnesium-aluminum alloy, aluminum-lithium alloy, aluminum-scandium-lithium alloy, magnesium-silver alloy and the like can be used. Similarly to the anode, the cathode can be produced by forming a thin film by a method such as vapor deposition or sputtering. Moreover, you may take out light emission from the cathode side as needed.

(Light emitting layer)
The light emitting layer is an organic layer having a light emitting function and is formed of one layer or a plurality of layers, and one of them contains the first host material, the second host material, and the light emitting material as described above.
When the light emitting layer is composed of a plurality of layers, the light emitting layer other than the above includes a host material and a dopant material when a doping system is employed. At this time, the host material mainly has a function of encouraging recombination of electrons and holes and confining excitons in the light emitting layer, and the dopant material efficiently emits excitons obtained by recombination. It has a function.
In the case of a phosphorescent element, the host material mainly has a function of confining excitons generated by the dopant in the light emitting layer.

The above light emitting layer may adopt a double dopant in which each dopant emits light by adding two or more kinds of dopant materials having a high quantum yield. Specifically, a mode in which yellow light emission is realized by co-evaporating a host, a red dopant, and a green dopant to make the light emitting layer common.

The above light-emitting layer is a laminate in which a plurality of light-emitting layers are stacked, so that electrons and holes are accumulated at the light-emitting layer interface, and the recombination region is concentrated at the light-emitting layer interface to improve quantum efficiency. Can do.
The ease of injecting holes into the light emitting layer may be different from the ease of injecting electrons, and the hole transport ability and electron transport ability expressed by the mobility of holes and electrons in the light emitting layer may be different. May be different.

A light emitting layer can be formed by well-known methods, such as a vapor deposition method, a spin coat method, LB method, for example. The light emitting layer can also be formed by thinning a solution obtained by dissolving a binder such as a resin and a material compound in a solvent by a spin coating method or the like.
The light emitting layer is preferably a molecular deposited film. The molecular deposited film is a thin film formed by deposition from a material compound in a gas phase state or a film formed by solidifying from a material compound in a solution state or a liquid phase state. The thin film (molecular accumulation film) formed by the LB method can be classified by the difference in the aggregation structure and the higher-order structure, and the functional difference resulting therefrom.
The content ratio of the first host material and the second host material in the light emitting layer is not particularly limited and can be adjusted as appropriate. Preferably, the mass ratio of the first host material: second host material = 1: 99 to 99: 1 Within the range, more preferably within the range of 10:90 to 90:10.

The phosphorescent dopant (phosphorescent material) that forms the light emitting layer is a compound that can emit light from the triplet excited state, and is not particularly limited as long as it emits light from the triplet excited state, but Ir, Pt, Os, Au, Cu, An organometallic complex containing at least one metal selected from Re and Ru and a ligand is preferable. The ligand preferably has an ortho metal bond. A metal complex containing a metal atom selected from Ir, Os and Pt is preferred in that the phosphorescent quantum yield is high and the external quantum efficiency of the light emitting device can be further improved. Are more preferable, iridium complexes and platinum complexes are more preferable, and orthometalated iridium complexes are particularly preferable.

The content of the phosphorescent dopant in the light emitting layer is not particularly limited and may be appropriately selected depending on the intended purpose. For example, it is preferably 0.1 to 70% by mass, more preferably 1 to 30% by mass. If the phosphorescent dopant content is 0.1% by mass or more, sufficient light emission can be obtained, and if it is 70% by mass or less, concentration quenching can be avoided.

Specific examples of preferred organometallic complexes as phosphorescent dopants are shown below.

A phosphorescent dopant material may be used independently and may use 2 or more types together.
The emission wavelength of the phosphorescent dopant material contained in the light emitting layer is not particularly limited, but at least one of the phosphorescent dopant materials contained in the light emitting layer preferably has a peak emission wavelength of 490 nm to 700 nm. More preferably, it is 650 nm or less.

The phosphorescent host is a compound having a function of efficiently emitting the phosphorescent dopant by efficiently confining the triplet energy of the phosphorescent dopant in the light emitting layer. In the organic EL device of the present invention, compounds other than the first host material and the second host material can be appropriately selected as a phosphorescent host according to the purpose.
The first host material and the second host material and other compounds may be used in combination as a phosphorescent host material in the same light emitting layer. When there are a plurality of light emitting layers, one of the light emitting layers The first host material and the second host material may be used as the phosphorescent host material, and a compound other than the first host material or the second host material may be used as the phosphorescent host material of another light emitting layer. The first host material and the second host material can also be used for organic layers other than the light emitting layer.

Specific examples of compounds other than the first host material and the second host material and suitable as a phosphorescent host include carbazole derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline. Derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethylidene compounds , Porphyrin compounds, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimide derivatives, fluoresceins Represented by metal complexes of redenemethane derivatives, distyrylpyrazine derivatives, heterocyclic tetracarboxylic anhydrides such as naphthaleneperylene, phthalocyanine derivatives, 8-quinolinol derivatives, metal phthalocyanines, metal complexes with benzoxazole and benzothiazole as ligands Various metal complexes polysilane compounds, poly (N-vinylcarbazole) derivatives, aniline copolymers, thiophene oligomers, conductive polymer oligomers such as polythiophene, polythiophene derivatives, polyphenylene derivatives, polyphenylene vinylene derivatives, polyfluorene derivatives, etc. Examples thereof include polymer compounds. Phosphorescent hosts other than the first host material and the second host material may be used alone or in combination of two or more. Specific examples include the following compounds.

The thickness of the light emitting layer is preferably 5 to 50 nm, more preferably 7 to 50 nm, and still more preferably 10 to 50 nm. When the thickness is 5 nm or more, it is easy to form a light emitting layer, and when the thickness is 50 nm or less, an increase in driving voltage can be avoided.

(Electron donating dopant)
The organic EL device of the present invention preferably has an electron donating dopant in the interface region between the cathode and the light emitting unit. According to such a configuration, it is possible to improve the light emission luminance and extend the life of the organic EL element. Here, the electron donating dopant means a material containing a metal having a work function of 3.8 eV or less, and specific examples thereof include alkali metals, alkali metal complexes, alkali metal compounds, alkaline earth metals, alkaline earths. Examples thereof include at least one selected from metal complexes, alkaline earth metal compounds, rare earth metals, rare earth metal complexes, rare earth metal compounds, and the like.

Examples of the alkali metal include Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV), Cs (work function: 1.95 eV), and the like. A function of 2.9 eV or less is particularly preferable. Of these, K, Rb, and Cs are preferred, Rb and Cs are more preferred, and Cs is most preferred. Examples of alkaline earth metals include Ca (work function: 2.9 eV), Sr (work function: 2.0 eV to 2.5 eV), Ba (work function: 2.52 eV), and the like. The thing below 9 eV is especially preferable. Examples of rare earth metals include Sc, Y, Ce, Tb, Yb, and the like, and those having a work function of 2.9 eV or less are particularly preferable.

Examples of the alkali metal compound include alkali oxides such as Li ₂ O, Cs ₂ O, and K ₂ O, and alkali halides such as LiF, NaF, CsF, and KF, and LiF, Li ₂ O, and NaF are preferable. Examples of the alkaline earth metal compound include BaO, SrO, CaO, and Ba _x Sr _1-x O (0 <x <1), Ba _x Ca _1-x O (0 <x <1) mixed with these. BaO, SrO, and CaO are preferable. The rare earth metal _{_{compound, YbF 3, ScF 3, ScO}} 3, Y 2 O 3, Ce 2 O 3, GdF 3, TbF 3 and the _{_{like, YbF 3, ScF 3, TbF}} 3 are preferable.

The alkali metal complex, alkaline earth metal complex, and rare earth metal complex are not particularly limited as long as each metal ion contains at least one of an alkali metal ion, an alkaline earth metal ion, and a rare earth metal ion. In addition, the ligand includes quinolinol, benzoquinolinol, acridinol, phenanthridinol, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxydiaryl oxadiazole, hydroxydiaryl thiadiazole, hydroxyphenyl pyridine, hydroxyphenyl benzimidazole, hydroxybenzotriazole, Hydroxyfulborane, bipyridyl, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene, β-diketones, azomethines, and derivatives thereof are preferred, but not limited thereto.

As an addition form of the electron donating dopant, it is preferable to form a layered or island shape in the interface region. As a forming method, while depositing an electron donating dopant by resistance heating vapor deposition, an organic compound (light emitting material or electron injecting material) that forms an interface region is simultaneously deposited, and the electron donating dopant is dispersed in the organic compound. Is preferred. The dispersion concentration is organic compound: electron donating dopant = 100: 1 to 1: 100, preferably 5: 1 to 1: 5 in molar ratio.

In the case where the electron donating dopant is formed in a layered form, after forming the light emitting material or the electron injecting material, which is an organic layer at the interface, in a layered form, the reducing dopant is vapor-deposited by a resistance heating vapor deposition method. .1 nm to 15 nm. When the electron donating dopant is formed in an island shape, after forming the light emitting material and the electron injecting material, which are organic layers at the interface, in an island shape, the electron donating dopant is deposited by resistance heating vapor deposition alone, preferably The island is formed with a thickness of 0.05 nm to 1 nm.
In the organic EL device of the present invention, the ratio of the main component to the electron donating dopant is preferably the main component: electron donating dopant = 5: 1 to 1: 5 in a molar ratio of 2: 1 to 1: 2. More preferably.

(Electron transport layer)
The electron transport layer is an organic layer formed between the light emitting layer and the cathode, and has a function of transporting electrons from the cathode to the light emitting layer. When the electron transport layer is composed of a plurality of layers, an organic layer close to the cathode may be defined as an electron injection layer. The electron injection layer has a function of efficiently injecting electrons from the cathode into the organic layer unit.

As the electron transporting material used for the electron transporting layer, an aromatic heterocyclic compound containing one or more heteroatoms in the molecule is preferably used, and a nitrogen-containing ring derivative is particularly preferable. The nitrogen-containing ring derivative is preferably an aromatic ring having a nitrogen-containing 6-membered ring or 5-membered ring skeleton, or a condensed aromatic ring compound having a nitrogen-containing 6-membered ring or 5-membered ring skeleton.
As this nitrogen-containing ring derivative, for example, a nitrogen-containing ring metal chelate complex represented by the following formula (AA) is preferable.

R ² to R ⁷ in formula (AA) are each independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, an amino group, a hydrocarbon group having 1 to 40 carbon atoms, or an alkoxy group having 1 to 40 carbon atoms. , An aryloxy group having 6 to 50 carbon atoms, an alkoxycarbonyl group, or an aromatic heterocyclic group having 5 to 50 ring carbon atoms, which may be substituted.

Examples of the halogen atom include fluorine, chlorine, bromine, iodine and the like.
Examples of the amino group which may be substituted include an alkylamino group, an arylamino group and an aralkylamino group.
The alkylamino group and the aralkylamino group are represented as —NQ ¹ Q ² . Q ¹ and Q ² each independently represents an alkyl group having 1 to 20 carbon atoms or an aralkyl group having 1 to 20 carbon atoms. One of Q ¹ and Q ² may be a hydrogen atom or a deuterium atom.
The arylamino group is represented as —NAr ¹ Ar ^2, and Ar ¹ and Ar ² each independently represents a non-condensed aromatic hydrocarbon group or a condensed aromatic hydrocarbon group having 6 to 50 carbon atoms. One of Ar ¹ and Ar ² may be a hydrogen atom or a deuterium atom.

The hydrocarbon group having 1 to 40 carbon atoms includes an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, and an aralkyl group.
The alkoxycarbonyl group is represented as —COOY ′, and Y ′ represents an alkyl group having 1 to 20 carbon atoms.
M in the formula (AA) is aluminum (Al), gallium (Ga), or indium (In), and is preferably In.
L in the formula (AA) is a group represented by the following formula (A ′) or (A ″).

In the formula (A ′), R ⁸ to R ¹² are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted hydrocarbon group having 1 to 40 carbon atoms, and groups adjacent to each other are cyclic structures May be formed. In the formula (A ″), R ¹³ to R ²⁷ are each independently a hydrogen atom, a deuterium atom or a substituted or unsubstituted hydrocarbon group having 1 to 40 carbon atoms, and groups adjacent to each other are An annular structure may be formed.

The hydrocarbon group having 1 to 40 carbon atoms represented by R ⁸ to R ¹² and R ¹³ to R ^{27 in the} formula (A ′) and the formula (A ″) is represented by R ² to R ⁷ in the formula (A). The divalent group in the case where the adjacent groups of R ⁸ to R ¹² and R ¹³ to R ²⁷ form a cyclic structure includes a tetramethylene group, a pentamethylene group, a hexamethylene group, and the like. Examples include a methylene group, diphenylmethane-2,2′-diyl group, diphenylethane-3,3′-diyl group, and diphenylpropane-4,4′-diyl group.

As the electron transport compound used in the electron transport layer, 8-hydroxyquinoline or a metal complex of its derivative, an oxadiazole derivative, or a nitrogen-containing heterocyclic derivative is preferable. As a specific example of the metal complex of 8-hydroxyquinoline or a derivative thereof, a metal chelate oxinoid compound containing a chelate of oxine (generally 8-quinolinol or 8-hydroxyquinoline) such as tris (8-quinolinol) aluminum is used. Can do. And as an oxadiazole derivative, the following can be mentioned.

In the above formula, Ar ¹⁷ , Ar ¹⁸ , Ar ¹⁹ , Ar ²¹ , Ar ²² and Ar ²⁵ each represent a substituted or unsubstituted aromatic hydrocarbon group or condensed aromatic hydrocarbon group having 6 to 50 carbon atoms, Ar ¹⁷ and Ar ¹⁸ , Ar ¹⁹ and Ar ²¹ , Ar ²² and Ar ²⁵ may be the same or different. Examples of the aromatic hydrocarbon group or the condensed aromatic hydrocarbon group include a phenyl group, a naphthyl group, a biphenyl group, an anthranyl group, a perylenyl group, and a pyrenyl group. Examples of these substituents include alkyl groups having 1 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, and cyano groups.

Ar ²⁰ , Ar ^23, and Ar ²⁴ each represent a substituted or unsubstituted divalent aromatic hydrocarbon group or condensed aromatic hydrocarbon group having 6 to 50 carbon atoms, and Ar ²³ and Ar ²⁴ are identical to each other. But it can be different. Examples of the divalent aromatic hydrocarbon group or condensed aromatic hydrocarbon group include a phenylene group, a naphthylene group, a biphenylene group, an anthranylene group, a peryleneylene group, and a pyrenylene group. Examples of these substituents include alkyl groups having 1 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, and cyano groups.

As these electron transport compounds, those having good thin film forming properties are preferably used. Specific examples of these electron transfer compounds include the following.

The nitrogen-containing heterocyclic derivative as the electron transfer compound is a nitrogen-containing heterocyclic derivative composed of an organic compound having the following formula, and includes a nitrogen-containing compound that is not a metal complex. Examples thereof include a 5-membered ring or 6-membered ring containing a skeleton represented by the following formula (B) and a structure represented by the following formula (C).

In the formula (C), X represents a carbon atom or a nitrogen atom. Z ₁ and Z ₂ each independently represents an atomic group capable of forming a nitrogen-containing heterocycle.

The nitrogen-containing heterocyclic derivative is more preferably an organic compound having a nitrogen-containing aromatic polycyclic group consisting of a 5-membered ring or a 6-membered ring. Further, in the case of such a nitrogen-containing aromatic polycyclic group having a plurality of nitrogen atoms, the nitrogen-containing compound having a skeleton in which the above formulas (B) and (C) or the above formula (B) and the following formula (D) are combined. Aromatic polycyclic organic compounds are preferred.

The nitrogen-containing group of the nitrogen-containing aromatic polycyclic organic compound is selected from, for example, nitrogen-containing heterocyclic groups represented by the following formulae.

In each of the above formulas, R is an aromatic hydrocarbon group or condensed aromatic hydrocarbon group having 6 to 40 carbon atoms, an aromatic heterocyclic group or condensed aromatic heterocyclic group having 3 to 40 carbon atoms, 1 to 20 is an alkyl group or an alkoxy group having 1 to 20 carbon atoms, n is an integer of 0 to 5, and when n is an integer of 2 or more, a plurality of R may be the same or different from each other.

Furthermore, preferred specific compounds include nitrogen-containing heterocyclic derivatives represented by the following formula (D1).
HAr-L ¹ -Ar ¹ -Ar ² (D1)
In the formula (D1), HAr is a substituted or unsubstituted nitrogen-containing heterocyclic group having 3 to 40 carbon atoms, and L ¹ is a single bond, substituted or unsubstituted aromatic hydrocarbon having 6 to 40 carbon atoms. A group, a condensed aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group having 3 to 40 carbon atoms or a condensed aromatic heterocyclic group, and Ar ¹ is a substituted or unsubstituted 2 to 6 carbon atom having 2 to 6 carbon atoms. And Ar ² represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 carbon atoms, a condensed aromatic hydrocarbon group, or a substituted or unsubstituted aromatic group having 3 to 40 carbon atoms. It is a heterocyclic group or a condensed aromatic heterocyclic group.

HAr in the formula (D1) is selected from the following group, for example.

L ¹ in the formula (D1) is selected from the following group, for example.

Ar ¹ in the formula (D1) is selected from, for example, arylanthranyl groups of the following formulas (D2) and (D3).

In the formulas (D2) and (D3), R ¹ to R ¹⁴ each independently represents a hydrogen atom, a deuterium atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, or an alkoxy having 1 to 20 carbon atoms. Group, aryloxy group having 6 to 40 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group or condensed aromatic hydrocarbon group having 6 to 40 carbon atoms, or substituted or unsubstituted aromatic group having 3 to 40 carbon atoms A heterocyclic group or a condensed aromatic heterocyclic group, and Ar ³ represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 carbon atoms, a condensed aromatic hydrocarbon group, or a substituted or unsubstituted carbon group having 3 to 40 aromatic heterocyclic groups or condensed aromatic heterocyclic groups. R ¹ to R ⁸ may be nitrogen-containing heterocyclic derivatives each of which is a hydrogen atom or a deuterium atom.

Ar ² in the formula (D1) is selected from the following group, for example.

In addition to this, the following compounds are also preferably used as the nitrogen-containing aromatic polycyclic organic compound as the electron transporting compound.

In the formula (D4), R ₁ to R ₄ each independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted aliphatic group having 1 to 20 carbon atoms, a substituted or unsubstituted carbon number of 3 to 20 An aliphatic cyclic group, a substituted or unsubstituted aromatic ring group having 6 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having 3 to 50 carbon atoms, and X ₁ and X ₂ are each independently Represents an oxygen atom, a sulfur atom, or a dicyanomethylene group.

In addition, the following compounds are also preferably used as the electron transfer compound.

In the formula (D5), R ¹ , R ² , R ³ and R ⁴ are the same or different groups, and are an aromatic hydrocarbon group or a condensed aromatic hydrocarbon group represented by the following formula (D6) It is.

In the formula (D6), R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ are the same or different from each other, and are a hydrogen atom, a deuterium atom, a saturated or unsaturated alkoxy group having 1 to 20 carbon atoms. A saturated or unsaturated alkyl group having 1 to 20 carbon atoms, an amino group, or an alkylamino group having 1 to 20 carbon atoms. At least one of R ⁵ , R ⁶ , R ⁷ , R ⁸ and R ⁹ is a group other than a hydrogen atom or a deuterium atom.

Furthermore, the electron transfer compound may be a polymer compound containing the nitrogen-containing heterocyclic group or the nitrogen-containing heterocyclic derivative.

The electron transport layer of the organic EL device of the present invention particularly preferably contains at least one nitrogen-containing heterocyclic derivative represented by the following formulas (E) to (G).

(In the formulas (E) to (G), Z ¹ , Z ^2, and Z ³ are each independently a nitrogen atom or a carbon atom.
R ¹ and R ² are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, substituted or unsubstituted carbon An alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.
n is an integer of 0 to 5, and when n is an integer of 2 or more, the plurality of R ¹ may be the same or different from each other. Further, two adjacent R ^{1 's} may be bonded to each other to form a substituted or unsubstituted hydrocarbon ring.
Ar ¹ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.
Ar ² is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted Alternatively, it is an unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.
However, either Ar ¹ or Ar ² is a substituted or unsubstituted condensed aromatic hydrocarbon ring group having 10 to 50 ring carbon atoms or a substituted or unsubstituted condensed aromatic group having 9 to 50 ring atoms. It is a heterocyclic group.
Ar ³ is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 50 ring atoms.
L ¹ , L ² and L ³ are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a divalent or substituted or unsubstituted divalent atom having 9 to 50 ring atoms. A condensed aromatic heterocyclic group. )

Examples of the aryl group having 6 to 50 ring carbon atoms include phenyl group, naphthyl group, anthryl group, phenanthryl group, naphthacenyl group, chrysenyl group, pyrenyl group, biphenyl group, terphenyl group, tolyl group, fluoranthenyl group, fluorenyl Groups and the like.
Examples of heteroaryl groups having 5 to 50 ring atoms include pyrrolyl, furyl, thienyl, silolyl, pyridyl, quinolyl, isoquinolyl, benzofuryl, imidazolyl, pyrimidyl, carbazolyl, selenophenyl Group, oxadiazolyl group, triazolyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinoxalinyl group, acridinyl group, imidazo [1,2-a] pyridinyl group, imidazo [1,2-a] pyrimidinyl group and the like.
Examples of the alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group.
Examples of the haloalkyl group having 1 to 20 carbon atoms include groups obtained by substituting one or more hydrogen atoms of the alkyl group with at least one halogen atom selected from fluorine, chlorine, iodine and bromine.
Examples of the alkoxy group having 1 to 20 carbon atoms include groups having the above alkyl group as an alkyl moiety.
Examples of the arylene group having 6 to 50 ring carbon atoms include groups obtained by removing one hydrogen atom from the aryl group.
Examples of the divalent condensed aromatic heterocyclic group having 9 to 50 ring atoms include groups obtained by removing one hydrogen atom from the condensed aromatic heterocyclic group described as the heteroaryl group.

The thickness of the electron transport layer is not particularly limited, but is preferably 1 nm to 100 nm.
Moreover, it is preferable to use an insulator or a semiconductor as an inorganic compound in addition to the nitrogen-containing ring derivative as a component of the electron injection layer that can be provided adjacent to the electron transport layer. If the electron injection layer is made of an insulator or a semiconductor, current leakage can be effectively prevented and the electron injection property can be improved.

As such an insulator, it is preferable to use at least one metal compound selected from the group consisting of alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides and alkaline earth metal halides. If the electron injection layer is composed of these alkali metal chalcogenides or the like, it is preferable in that the electron injection property can be further improved. Specifically, preferable alkali metal chalcogenides include, for example, Li ₂ O, K ₂ O, Na ₂ S, Na ₂ Se, and Na ₂ O, and preferable alkaline earth metal chalcogenides include, for example, CaO, BaO. , SrO, BeO, BaS and CaSe. Further, preferable alkali metal halides include, for example, LiF, NaF, KF, LiCl, KCl, and NaCl. Examples of preferable alkaline earth metal halides include fluorides such as CaF ₂ , BaF ₂ , SrF ₂ , MgF ₂ and BeF ₂ , and halides other than fluorides.

Further, as a semiconductor, an oxide, nitride, or oxynitride containing at least one element of Ba, Ca, Sr, Yb, Al, Ga, In, Li, Na, Cd, Mg, Si, Ta, Sb, and Zn. One kind alone or a combination of two or more kinds of products may be mentioned. In addition, the inorganic compound constituting the electron injection layer is preferably a microcrystalline or amorphous insulating thin film. If the electron injection layer is composed of these insulating thin films, a more uniform thin film is formed, and pixel defects such as dark spots can be reduced. Examples of such inorganic compounds include alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides, and alkaline earth metal halides.

When such an insulator or semiconductor is used, the preferred thickness of the layer is about 0.1 nm to 15 nm. Further, the electron injection layer in the present invention is preferable even if it contains the above-mentioned electron donating dopant.

(Hole transport layer)
An organic layer formed between the light emitting layer and the anode, and has a function of transporting holes from the anode to the light emitting layer. When the hole transport layer is composed of a plurality of layers, an organic layer close to the anode may be defined as a hole injection layer. The hole injection layer has a function of efficiently injecting holes from the anode into the organic layer unit.
As another material for forming the hole transport layer, an aromatic amine compound, for example, an aromatic amine derivative represented by the following formula (H) is preferably used.

In the formula (H), Ar ¹ to Ar ⁴ represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms or a condensed aromatic hydrocarbon group, a substituted or unsubstituted ring forming atom number of 5 to 50 aromatic heterocyclic groups or condensed aromatic heterocyclic groups, or a group in which these aromatic hydrocarbon groups or condensed aromatic hydrocarbon groups and aromatic heterocyclic groups or condensed aromatic heterocyclic groups are bonded.
In the formula (H), L represents a substituted or unsubstituted aromatic hydrocarbon group or condensed aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted ring forming atom number of 5 to 50. Represents an aromatic heterocyclic group or a condensed aromatic heterocyclic group.

Specific examples of the compound of formula (H) are described below.

An aromatic amine represented by the following formula (J) is also preferably used for forming the hole transport layer.

In the formula (J), the definitions of Ar ¹ to Ar ³ are the same as the definitions of Ar ¹ to Ar ^{4 in} the formula (H). Specific examples of the compound of formula (J) are shown below, but are not limited thereto.

The hole transport layer of the organic EL device of the present invention may have a two-layer structure of a first hole transport layer (anode side) and a second hole transport layer (cathode side).
The thickness of the hole transport layer is not particularly limited, but is preferably 10 to 200 nm.

In the organic EL device of the present invention, a layer containing an acceptor material may be bonded to the anode side of the hole transport layer or the first hole transport layer. This is expected to reduce drive voltage and manufacturing costs.
As the acceptor material, a compound represented by the following formula (K) is preferable.

(In the above formula (K), R ₂₁ to R ₂₆ may be the same as or different from each other, and are each independently a cyano group, —CONH ₂ , carboxyl group, or —COOR ₂₇ (R ₂₇ is a group having 1 to 20 carbon atoms) Represents an alkyl group or a cycloalkyl group having 3 to 20 carbon atoms, provided that one or more pairs of R ₂₁ and R ₂₂ , R ₂₃ and R ₂₄ , and R ₂₅ and R ₂₆ are combined together. A group represented by —CO—O—CO— may be formed.)
Examples of R ₂₇ include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, a cyclopentyl group, and a cyclohexyl group.
The thickness of the layer containing the acceptor material is not particularly limited, but is preferably 5 to 20 nm.

(N / p doping)
In the hole transport layer and the electron transport layer described above, as described in Japanese Patent No. 3695714, the carrier injection ability is improved by doping the donor material (n) and acceptor material (p). Can be adjusted.
A typical example of n doping is a method of doping a metal such as Li or Cs into an electron transport material, and a typical example of p doping is F ₄ TCNQ (2, 3, 5, 6) as a hole transport material. -Tetrafluoro-7,7,8,8-tetracyanoquinodimethane) and the like.

(Space layer)
For example, when the fluorescent layer and the phosphorescent layer are laminated, the space layer is a fluorescent layer for the purpose of adjusting the carrier balance so that excitons generated in the phosphorescent layer are not diffused into the fluorescent layer. It is a layer provided between the layer and the phosphorescent light emitting layer. In addition, the space layer can be provided between the plurality of phosphorescent light emitting layers.
Since the space layer is provided between the light emitting layers, a material having both electron transport properties and hole transport properties is preferable. In order to prevent diffusion of triplet energy in the adjacent phosphorescent light emitting layer, the triplet energy is preferably 2.6 eV or more. Examples of the material used for the space layer include the same materials as those used for the above-described hole transport layer.

(Barrier layer)
The organic EL device of the present invention preferably has a barrier layer such as an electron barrier layer, a hole barrier layer, or a triplet barrier layer in a portion adjacent to the light emitting layer. Here, the electron barrier layer is a layer that prevents electrons from leaking from the light emitting layer to the hole transport layer, and the hole barrier layer is a layer that prevents holes from leaking from the light emitting layer to the electron transport layer. is there.
The triplet barrier layer prevents the triplet excitons generated in the light emitting layer from diffusing into the surrounding layers, and confins the triplet excitons in the light emitting layer, thereby transporting electrons other than the light emitting dopant of the triplet excitons. It has a function of suppressing energy deactivation on the molecules of the layer.
In the case where a triplet barrier layer is provided, in the phosphorescent device, when the triplet energy of the phosphorescent dopant in the light emitting layer is E ^T _d and the triplet energy of the compound used as the triplet barrier layer is E ^T _TB , E ^T _d < If the energy level relationship of E ^T _TB is satisfied, the triplet exciton of the phosphorescent dopant is confined (cannot move to other molecules) due to the energy relationship, and the energy deactivation path other than light emission on the dopant is interrupted. It is assumed that light can be emitted with high efficiency. However, even if the relationship of E ^T _d <E ^T _TB is satisfied, if this energy difference ΔE ^T = E ^T _TB −E ^T _d is small, the actual device drive environment is at about room temperature. , endothermically triplet excitons overcame this energy difference Delta] E ^T by thermal energy near is considered to be possible to move to another molecule. In particular, in the case of phosphorescence emission, the exciton lifetime is longer than that of fluorescence emission, so that the influence of the endothermic exciton transfer process is likely to appear. The energy difference ΔE ^T is preferably as large as possible relative to the thermal energy at room temperature, more preferably 0.1 eV or more, and particularly preferably 0.2 eV or more.

Further, the electron mobility of the material constituting the triplet barrier layer is preferably 10 ⁻⁶ cm ² / Vs or more in the range of the electric field strength of 0.04 to 0.5 MV / cm. As a method for measuring the electron mobility of an organic material, several methods such as the Time of Flight method are known. Here, the electron mobility is determined by impedance spectroscopy.
The electron injection layer is desirably 10 ⁻⁶ cm ² / Vs or more in the range of electric field strength of 0.04 to 0.5 MV / cm. This facilitates the injection of electrons from the cathode into the electron transport layer, and also promotes the injection of electrons into the adjacent barrier layer and the light emitting layer, thereby enabling driving at a lower voltage.

Next, the present invention will be described in more detail using examples, but the present invention is not limited to the following examples.

[Synthesis of materials for organic EL elements]
Synthesis Example 1 (Synthesis of Compound H1)
Synthesis Example (1-1): Synthesis of Intermediate 1

Under a stream of argon, 2-nitro-1,4-dibromobenzene (11.2 g, 40 mmol), phenylboronic acid (4.9 g, 40 mmol), tetrakis (triphenylphosphine) palladium (1.39 g, 1.2 mmol), Toluene (120 mL) and 2M aqueous sodium carbonate solution (60 mL) were sequentially added, and the mixture was heated to reflux for 8 hours.
After cooling the reaction solution to room temperature, the organic layer was separated, and the organic solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain Intermediate 1 (6.6 g, yield 59%). The intermediate body 1 was identified by analysis of FD-MS (field desorption mass spectrum).

Synthesis Example (1-2): Synthesis of Intermediate 2

Under an argon stream, intermediate 1 (6.6 g, 23.7 mmol), triphenylphosphine (15.6 g, 59.3 mmol), and o-dichlorobenzene (24 mL) were sequentially added and heated at 180 ° C. for 8 hours.
The reaction solution was cooled to room temperature and then purified by silica gel column chromatography to obtain Intermediate 2 (4 g, yield 68%). The intermediate body 2 was identified by analysis of FD-MS (field desorption mass spectrum).

Synthesis Example (1-3): Synthesis of Intermediate 3

In the synthesis of Intermediate 1, intermediate 2 was used instead of 2-nitro-1,4-dibromobenzene, and 9-phenylcarbazol-3-ylboronic acid was used instead of phenylboronic acid. . The powder was identified as Intermediate 3 by FD-MS (field desorption mass spectrum) analysis.

Synthesis Example (1-4): Synthesis of Compound H1

Under an argon stream, intermediate 3 (1.6 g, 3.9 mmol), 4-bromobenzonitrile (0.71 g, 3.9 mmol), tris (dibenzylideneacetone) dipalladium (0.071 g, 0.078 mmol), Tri-t-butylphosphonium tetrafluoroborate (0.091 g, 0.31 mmol), t-butoxy sodium (0.53 g, 5.5 mmol), and anhydrous toluene (20 mL) were sequentially added, and the mixture was heated to reflux for 8 hours.
After cooling the reaction solution to room temperature, the organic layer was separated, and the organic solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 0.79 g of a white solid (H1).
FD-MS (field desorption mass spectrum), ultraviolet absorption maximum wavelength UV (PhMe) in a toluene solution; λmax, and fluorescence emission maximum wavelength FL (PhMe, λex = 300 nm); Shown in
FDMS, calcd for C37H23N3 = 509, found m / z = 509 (M +)
UV (PhMe); λmax, 324 nm, FL (PhMe, λex = 300 nm); λmax, 376 nm

Synthesis Example 2 (Synthesis of Compound H2)

The compound H1 was synthesized in the same manner using 4′-bromobiphenyl-3-carbonitrile instead of 4-bromobenzonitrile.
FD-MS (field desorption mass spectrum), ultraviolet absorption maximum wavelength UV (PhMe) in a toluene solution; λmax, and fluorescence emission maximum wavelength FL (PhMe, λex = 300 nm); Shown in
FDMS, calcd for C43H27N3 = 585, found m / z = 585 (M +)
UV (PhMe); λmax, 322 nm, FL (PhMe, λex = 300 nm); λmax, 375 nm

Synthesis Example 3 (Synthesis of Compound H3)

The compound H1 was synthesized in the same manner using 4′-bromobiphenyl-4-carbonitrile instead of 4-bromobenzonitrile.
With respect to the obtained compound, FD-MS (field desorption mass spectrum), ultraviolet absorption maximum wavelength UV (PhMe) in a toluene solution; λmax, and fluorescence emission maximum wavelength UV (PhMe); λmax are shown below.
FDMS, calcd for C43H27N3 = 585, found m / z = 585 (M +)
UV (PhMe); λmax, 324 nm, FL (PhMe, λex = 300 nm); λmax, 393 nm

Synthesis Example 4 (Synthesis of Compound H4)

The compound H1 was synthesized in the same manner using 3′-bromobiphenyl-4-carbonitrile instead of 4-bromobenzonitrile.
FD-MS (field desorption mass spectrum), ultraviolet absorption maximum wavelength UV (PhMe) in a toluene solution; λmax, and fluorescence emission maximum wavelength FL (PhMe, λex = 300 nm); Shown in
FDMS, calcd for C43H27N3 = 585, found m / z = 585 (M +)
UV (PhMe); λmax, 322 nm, FL (PhMe, λex = 300 nm); λmax, 376 nm

Synthesis Example 5 (Synthesis of Compound H5)
Synthesis Example (5-1): Synthesis of Intermediate 4

In the synthesis of Intermediate 1, 3-bromocarbazole was used in place of 2-nitro-1,4-dibromobenzene, and 9-phenylcarbazol-3-ylboronic acid was used in place of phenylboronic acid. did. The powder was identified as Intermediate 4 by FD-MS (field desorption mass spectrum) analysis.

Synthesis Example (5-2): Synthesis of Compound H5

In the synthesis of Compound H1, Intermediate 4 was used instead of Intermediate 3, and the same method was used.
FD-MS (field desorption mass spectrum), ultraviolet absorption maximum wavelength UV (PhMe) in a toluene solution; λmax, and fluorescence emission maximum wavelength FL (PhMe, λex = 300 nm); Shown in
FDMS, calcd for C37H23N3 = 509, found m / z = 509 (M +)
UV (PhMe); λmax, 339 nm, FL (PhMe, λex = 300 nm); λmax, 404 nm

Synthesis Example 6 (Synthesis of Compound H6)

In the synthesis of Compound H1, 4′-bromobiphenyl-3-carbonitrile was used instead of 4-bromobenzonitrile, and Intermediate 4 was used instead of Intermediate 3, and the compound H1 was synthesized in the same manner.
FD-MS (field desorption mass spectrum) of the obtained compound is shown below.
FDMS, calcd for C43H27N3 = 585, found m / z = 585 (M +)

Synthesis Example 7 (Synthesis of Compound H7)

In the synthesis of Compound H1, 4′-bromobiphenyl-4-carbonitrile was used instead of 4-bromobenzonitrile, and Intermediate 4 was used instead of Intermediate 3, and the compound H1 was synthesized in the same manner.
FD-MS (field desorption mass spectrum) of the obtained compound is shown below.
FDMS, calcd for C43H27N3 = 585, found m / z = 585 (M +)

Synthesis Example 8 (Synthesis of Compound H8)

In the synthesis of Compound H1, 3′-bromobiphenyl-4-carbonitrile was used instead of 4-bromobenzonitrile, and Intermediate 4 was used instead of Intermediate 3, and the compound H1 was synthesized in the same manner.
FD-MS (field desorption mass spectrum) of the obtained compound is shown below.
FDMS, calcd for C43H27N3 = 585, found m / z = 585 (M +)

Synthesis Example 9 (Synthesis of Compound H9)

In the synthesis of Compound H1, 3′-bromobiphenyl-3-carbonitrile was used instead of 4-bromobenzonitrile, and Intermediate 4 was used instead of Intermediate 3, and the synthesis was performed in the same manner.
FD-MS (field desorption mass spectrum) of the obtained compound is shown below.
FDMS, calcd for C43H27N3 = 585, found m / z = 585 (M +)

Synthesis Example 10 (Synthesis of Compound H10)
Synthesis Example (10-1): Synthesis of Intermediate 5

In the synthesis of Intermediate 1, 1-bromo-4-iodobenzene was used in place of 2-nitro-1,4-dibromobenzene, and 9-phenylcarbazol-3-ylboronic acid was used in place of phenylboronic acid. The method was synthesized. The intermediate body 5 was identified by analysis of FD-MS (field desorption mass spectrum).

Synthesis Example (10-2): Synthesis of Intermediate 6

Under an argon stream, intermediate 5 (10 g, 25 mmol), bis (pinacolato) diboron (8.3 g, 33 mmol), [1,1′-bis (diphenylphosphino) ferrocene] palladium (II) dichloride dichloromethane adduct (0 .62 g, 0.75 mmol), potassium acetate (7.4 g, 75 mmol), and N, N-dimethylformamide (170 mL) were sequentially added, and the mixture was heated to reflux for 8 hours.
After cooling the reaction solution to room temperature, the organic layer was separated, and the organic solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain Intermediate 6 (10 g, yield 91%). The powder was identified as Intermediate 6 by FD-MS (field desorption mass spectrum) analysis.

Synthesis Example (10-3): Synthesis of Intermediate 7

In the synthesis of Intermediate 1, 3-bromocarbazole was used instead of 2-nitro-1,4-dibromobenzene, and Intermediate 6 was used instead of phenylboronic acid. The powder was identified as Intermediate 7 by FD-MS (field desorption mass spectrum) analysis.

Synthesis Example (10-4): Synthesis of H10

In the synthesis of Compound H1, 4′-bromobiphenyl-4-carbonitrile was used instead of 4-bromobenzonitrile, and Intermediate 7 was used instead of Intermediate 3, and the compound H1 was synthesized in the same manner.
FD-MS (field desorption mass spectrum) of the obtained compound is shown below.
FDMS, calcd for C49H31N3 = 661, found m / z = 661 (M +)

Synthesis Example 11 (Synthesis of Compound H11)

In the synthesis of Compound H1, 3′-bromobiphenyl-4-carbonitrile was used instead of 4-bromobenzonitrile, and Intermediate 7 was used instead of Intermediate 3, and the compound H1 was synthesized in the same manner.
FD-MS (field desorption mass spectrum) of the obtained compound is shown below.
FDMS, calcd for C49H31N3 = 661, found m / z = 661 (M +)

Synthesis Example 12 (Synthesis of Compound H12)

In the synthesis of Compound H1, 2-bromo-8-cyanodibenzofuran was used instead of 4-bromobenzonitrile, and Intermediate 4 was used instead of Intermediate 3, and the compound H1 was synthesized in the same manner.
FD-MS (field desorption mass spectrum) of the obtained compound is shown below.
FDMS, calcd for C43H25N3O = 599, found m / z = 599 (M +)

Synthesis Example 13 (Synthesis of Compound H13)
Synthesis Example (13-1): Synthesis of Intermediate 8

In the synthesis of Intermediate 1, 4-bromobenzonitrile was used instead of 2-nitro-1,4-dibromobenzene, and 9-phenylcarbazol-3-ylboronic acid was used instead of phenylboronic acid. Synthesized. The powder was identified as Intermediate 8 by FD-MS (field desorption mass spectrum) analysis.

Synthesis Example (13-2): Synthesis of Intermediate 9

Under an argon stream, N, N-dimethylformamide (80 mL), intermediate 8 (5.6 g, 16.3 mmol) and N-bromosuccinimide (3.5 g, 19.5 mmol) were sequentially added, and 8 ° C. was added. Stir for hours.
The reaction solution was returned to room temperature, added with water, filtered, and the resulting solid was purified by silica gel column chromatography to obtain Intermediate 8 (6.2 g, yield 90%). The powder was identified as Intermediate 9 by FD-MS (field desorption mass spectrum) analysis.

Synthesis Example (13-3): Synthesis of Compound H13

In the synthesis of Intermediate 1, intermediate 9 was used instead of 2-nitro-1,4-dibromobenzene, and 9-phenylcarbazol-3-ylboronic acid was used instead of phenylboronic acid. .
FD-MS (field desorption mass spectrum) of the obtained compound is shown below.
FDMS, calcd for C43H27N3 = 585, found m / z = 585 (M +)

Synthesis Example 14 (Synthesis of Compound H14)

In the synthesis of Intermediate 1, 3,5-dibromobenzonitrile (1 equivalent) was used instead of 2-nitro-1,4-dibromobenzene and 9-phenylcarbazol-3-ylboronic acid ( 2 equivalents) was synthesized in the same manner.
FD-MS (field desorption mass spectrum) of the obtained compound is shown below.
FDMS, calcd for C43H27N3 = 585, found m / z = 585 (M +)

Synthesis Example 15: Synthesis of Compound H15

The compound H1 was synthesized in the same manner using 2-bromo-8-cyanodibenzofuran instead of 4-bromobenzonitrile. FD-MS (field desorption mass spectrum) of the obtained compound is shown below.
FDMS, calcd for C43H25N3O = 599, found m / z = 599 (M +)

Synthesis Example 16 Synthesis of Compound H16

The compound H1 was synthesized in the same manner using 2-bromo-8-cyanodibenzothiophene instead of 4-bromobenzonitrile. FD-MS (field desorption mass spectrum) of the obtained compound is shown below.
FDMS, calcd for C43H25N3S = 615, found m / z = 615 (M +)

Synthesis Example 17 Synthesis of Compound H17

In the synthesis of Compound H1, 2-bromo-8-cyanodibenzothiophene was used instead of 4-bromobenzonitrile, and Intermediate 4 was used instead of Intermediate 3, and the compound H1 was synthesized in the same manner. FD-MS (field desorption mass spectrum) of the obtained compound is shown below.
FDMS, calcd for C43H25N3S = 615, found m / z = 615 (M +)

[Production of organic EL element and evaluation of light emission performance]

Example 1
(Manufacture of organic EL elements)
A glass substrate with an ITO transparent electrode of 25 mm × 75 mm × thickness 1.1 mm (manufactured by Geomatic Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes and then UV ozone cleaning for 30 minutes.
The glass substrate with the transparent electrode line after washing is mounted on the substrate holder of the vacuum deposition apparatus, and the following electron-accepting (acceptor) compound is first formed so as to cover the transparent electrode on the surface on which the transparent electrode line is formed. C-1 was vapor-deposited to form a compound C-1 film having a thickness of 5 nm. On the Compound C-1 film, the following aromatic amine derivative (Compound X1) was deposited as a first hole transport material to form a first hole transport layer having a thickness of 65 nm. Subsequent to the formation of the first hole transport layer, the following aromatic amine derivative (Compound X2) was deposited as a second hole transport material to form a second hole transport layer having a thickness of 10 nm.
Further, on the second hole transport layer, the host material 1 and the host material 2 described in Table 1 below as the host material and the following compound Ir (bzq) ₃ as the phosphorescent material are co-evaporated, and the film thickness is 25 nm. A phosphorescent light emitting layer was formed. The concentration of the compound Ir (bzq) ₃ in the light emitting layer was 10.0% by mass, the concentration of the host material 1 was 45.0% by mass, and the concentration of the host material 2 was 45.0% by mass. This co-deposited film functions as a light emitting layer.
Following the formation of the light emitting layer, the following compound ET was formed to a thickness of 35 nm. This compound ET film functions as an electron transport layer.
Next, LiF was used as an electron injecting electrode (cathode), and the film thickness was set to 1 nm at a film forming rate of 0.1 angstrom / min. Metal Al was vapor-deposited on this LiF film, and a metal cathode was formed with a film thickness of 80 nm to produce an organic EL device.
The compounds used in Examples and Comparative Examples are shown below.

(Emission characteristic evaluation of organic EL elements)
Luminous efficiency of the obtained organic EL device was measured at room temperature and DC constant current drive (current density 1 mA / cm ² ). Further, an 80% lifetime (time until the luminance is reduced to 80% of the initial luminance by constant current driving) at an initial luminance of 10,000 cd / m ² was obtained. The results are shown in Table 1.

Examples 2 to 5 and Comparative Example 1
An organic EL element was produced in the same manner as in Example 1 except that the light emitting layer was formed using the host material 1 and the host material 2 shown in Table 2 as the host material of the light emitting layer.
Table 1 shows the results of luminous efficiency and 80% lifetime of the obtained organic EL device.

From Table 1, the light emitting layer is obtained by combining the compounds H1 and H3 to H5 which are the first host materials represented by the formula (A) and the compound F2 or F3 which is the second host material represented by the formula (1). The organic EL elements of Examples 1 to 5 used as the host material (cohost) of Example 1 had good luminous efficiency. Furthermore, the organic EL devices of Examples 1 to 5 have a longer lifetime than the organic EL devices of Comparative Example 1 using the same central skeleton but the compound F1 and the compound F3, which are not substituted with cyano groups at the ends, as cohosts. It was converted.

Example 6
(Manufacture of organic EL elements)
A glass substrate (manufactured by Geomatic Co., Ltd.) with a transparent electrode (anode, 70 nm) having a thickness of 25 mm × 75 mm × 1.1 mm was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes and then UV ozone cleaning for 30 minutes. It was.
First, the cleaned glass substrate with a transparent electrode line is mounted on a substrate holder of a vacuum deposition apparatus, and the compound electrode C is formed by resistance heating vapor deposition so as to cover the transparent electrode on the surface on which the transparent electrode line is formed. -1 was laminated. As a result, a hole injection layer adjacent to the anode having a thickness of 10 nm was formed.
On this hole injection layer, compound X4 was laminated by resistance heating vapor deposition. This formed the 65-nm-thick 1st positive hole transport layer.
On this 1st positive hole transport layer, the compound X3 was laminated | stacked by resistance heating vapor deposition. As a result, a second hole transport layer having a thickness of 10 nm was formed.
On this second hole transport layer, compound H5 as the first host material, compound F2 as the second host material, and Ir (bzq) ₃ as the phosphorescent dopant were co-evaporated by resistance heating. This formed the 25-nm-thick light emitting layer which shows yellow light emission. In addition, the density | concentration of the 1st host material in the light emitting layer, the 2nd host material, and the luminescent dopant was 45 mass%, 45 mass%, and 10 mass%, respectively.
On this light emitting layer, the compound ET was laminated | stacked by resistance heating vapor deposition. Thereby, an electron transport layer having a thickness of 35 nm was formed.
Furthermore, LiF was vapor-deposited on the electron transport layer to form an electron injection layer having a thickness of 1 nm. Furthermore, metal Al was vapor-deposited on the electron injecting layer to form a cathode having a thickness of 80 nm.

(Emission characteristic evaluation of organic EL elements)
The voltage and external quantum efficiency of the obtained organic EL device at room temperature and DC constant current drive (current density 10 mA / cm ² ) were measured. Furthermore, a 90% lifetime at 50 mA / cm ² (time until the luminance decreases to 90% of the initial luminance by constant current driving) was obtained. The results are shown in Table 2.

Examples 7 to 17 and Comparative Examples 3 and 6 to 7
An organic EL device was produced in the same manner as in Example 6 except that the light emitting layer was formed using the host material 1 and the host material 2 shown in Table 2 as the host material of the light emitting layer.
Table 2 shows the results of the voltage, luminous efficiency, and 90% lifetime of the obtained organic EL device.

Comparative Examples 2, 4 and 5
An organic EL device was produced in the same manner as in Example 6 except that the light emitting layer was formed using the host material 2 (90% by mass) shown in Table 2 as the host material of the light emitting layer.
Table 2 shows the results of the voltage, luminous efficiency, and 90% lifetime of the obtained organic EL device.

From Table 2, the organic EL devices of Examples 6 to 15 using the compound represented by the formula (A) as the first host material and the compound represented by the formula (1) as the second host material were compared. The lifetime was longer than that of the organic EL elements of Examples 2 and 3.
Moreover, the implementation using the compound represented by the formula (A) as the first host material and the compound having one carbazole ring and azine ring in the molecule represented by the formula (1) as the second host material The organic EL elements of Examples 16 and 17 had a longer lifetime than the organic EL elements of Comparative Examples 4-7.

Example 18
(Manufacture of organic EL elements)
A glass substrate (manufactured by Geomatic Co., Ltd.) with a transparent ITO electrode (anode, 130 nm) having a thickness of 25 mm × 75 mm × 1.1 mm was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes and then UV ozone cleaning for 30 minutes. It was.
First, the cleaned glass substrate with a transparent electrode line is mounted on a substrate holder of a vacuum deposition apparatus, and the compound electrode C is formed by resistance heating vapor deposition so as to cover the transparent electrode on the surface on which the transparent electrode line is formed. -1 was laminated. This formed a hole injection layer adjacent to the 5 nm thick anode.
On this hole injection layer, compound X1 was laminated by resistance heating vapor deposition. As a result, a first hole transport layer having a thickness of 160 nm was formed.
On this 1st positive hole transport layer, the compound X3 was laminated | stacked by resistance heating vapor deposition. As a result, a second hole transport layer having a thickness of 10 nm was formed.
On this second hole transport layer, compound H5 as the first host material, compound F2 as the second host material, and Ir (ppy) ₃ as the phosphorescent dopant were co-deposited by resistance heating. Thus, a light emitting layer having a thickness of 25 nm and emitting green light was formed. In addition, the density | concentration of the 1st host material in the light emitting layer, the 2nd host material, and the luminescent dopant was 45 mass%, 45 mass%, and 10 mass%, respectively.
On this light emitting layer, the compound ET was laminated | stacked by resistance heating vapor deposition. Thereby, an electron transport layer having a thickness of 35 nm was formed.
Furthermore, LiF was vapor-deposited on the electron transport layer to form an electron injection layer having a thickness of 1 nm. Furthermore, metal Al was vapor-deposited on the electron injecting layer to form a cathode having a thickness of 80 nm.

(Emission characteristic evaluation of organic EL elements)
The voltage and external quantum efficiency of the obtained organic EL device at room temperature and DC constant current drive (current density 10 mA / cm ² ) were measured. Further, a 95% life (time until the luminance is reduced to 95% of the initial luminance by constant current driving) at an initial luminance of 4,000 cd / m ² was obtained. The results are shown in Table 3.

Examples 19 to 20 and Comparative Example 8
An organic EL device was produced in the same manner as in Example 18 except that the light emitting layer was formed using the host material 1 and the host material 2 shown in Table 3 as the host material of the light emitting layer.
Table 3 shows the results of the voltage, external quantum efficiency, and 95% lifetime of the obtained organic EL device.

The organic EL elements of Examples 18 to 20 using the compound represented by the formula (A) as the first host material and the compound represented by the formula (1) as the second host material are the organic EL elements of Comparative Example 8. The lifetime is longer than that of the EL element.

Examples 21 to 28 and Comparative Examples 9 to 11
An organic EL device was produced in the same manner as in Example 1 except that the light emitting layer was formed using the host material 1 and the host material 2 shown in Table 4 as the host material of the light emitting layer.
Table 4 shows the results of the luminous efficiency and 90% lifetime of the obtained organic EL device.

Examples 29 to 35 and Comparative Examples 12 to 14
An organic EL device was produced in the same manner as in Example 18 except that the light emitting layer was formed using the host material 1 and the host material 2 shown in Table 5 as the host material of the light emitting layer.
Table 5 shows the results of the voltage, external quantum efficiency, and 95% lifetime of the obtained organic EL device.

As described in detail above, the organic EL device of the present invention has a good long-life performance.

DESCRIPTION OF SYMBOLS 1 Organic electroluminescent element 2 Substrate 3 Anode 4 Cathode 5 Phosphorescent light emitting layer 6 Hole injection / transport layer 7 Electron injection / transport layer 10 Organic thin film layer

Claims

An organic electroluminescence device comprising at least a light emitting layer between an anode and a cathode, wherein the light emitting layer is represented by a first host material represented by the following general formula (A) and the following general formula (1): An organic electroluminescence device comprising: a second host material; and a light emitting material.

[In the formula (A),
A 1 and A 2 each independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
A 3 represents a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms.
m represents an integer of 0 to 3.
X 1 to X 8 and Y 1 to Y 8 each independently represent N or CR a .
R a is independently a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, substituted or unsubstituted It represents a substituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted silyl group, a halogen atom or a cyano group. When a plurality of R a are present, the plurality of R a may be the same or different.
One of X 5 to X 8 and one of Y 1 to Y 4 are bonded via A 3 .
Further, the formula (A) satisfies at least one of the following (i) to (v).
(I) At least one of A 1 and A 2 is an aromatic hydrocarbon group having 6 to 30 ring carbon atoms substituted with a cyano group, or a hetero ring having 5 to 30 ring atoms substituted with a cyano group. It is a cyclic group.
(Ii) At least one of X 1 to X 4 and Y 5 to Y 8 is CR a , and at least one of R a in X 1 to X 4 and Y 5 to Y 8 is substituted with a cyano group It is an aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a heterocyclic group having 5 to 30 ring atoms substituted with a cyano group.
(Iii) m is an integer of 1 to 3, and at least one of A 3 is substituted with a divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms substituted with a cyano group, or a cyano group And a divalent heterocyclic group having 5 to 30 ring atoms.
(Iv) At least one of X 5 to X 8 and Y 1 to Y 4 is CR a , and at least one of R a in X 5 to X 8 and Y 1 to Y 8 is substituted with a cyano group It is an aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a heterocyclic group having 5 to 30 ring atoms substituted with a cyano group.
(V) At least one of X 1 to X 8 and Y 1 to Y 8 is C—CN. ]

[In general formula (1),
Z 1 represents a ring structure represented by the following general formula (1-1) or (1-2) condensed in a. Z 2 represents a ring structure represented by the following general formula (1-1) or (1-2) condensed at b. However, at least one of Z 1 and Z 2 is represented by the following general formula (1-1).
M 1 is a substituted or unsubstituted nitrogen-containing heteroaromatic ring having 5 to 30 ring atoms,
L 1 represents a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, a ring It represents a cycloalkylene group having 5 to 30 carbon atoms formed or a group in which these are linked.
k represents 1 or 2. ]

[In the above general formula (1-1),
c represents condensation in a or b in the general formula (1).
In the above (1-2), any one of d, e and f represents condensation in a or b in the general formula (1).
In the general formulas (1-1) and (1-2),
X 11 represents a sulfur atom, an oxygen atom, N—R 19 , or C (R 20 ) (R 21 ).
R 11 to R 21 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted ring formation. A heterocyclic group having 5 to 30 atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms Group, substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or It represents an unsubstituted aralkyl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms.
Adjacent R 11 to R 21 may be bonded to each other to form a ring. ]
The organic electroluminescence device according to claim 1, wherein the first host material satisfies at least one of (i) and (ii).
In the general formula (A), A 3 represents a substituted or unsubstituted divalent monocyclic hydrocarbon group having 6 or less ring carbon atoms, or a substituted or unsubstituted divalent monocyclic hydrocarbon group having 6 or less ring atoms. The organic electroluminescence device according to claim 1, which represents a ring heterocyclic group.
The organic electroluminescence device according to claim 1, wherein the second host material is represented by the following general formula (2).

[In general formula (2),
Z 1 represents a ring structure represented by the general formula (1-1) or (1-2) condensed in a. Z 2 represents a ring structure represented by the general formula (1-1) or (1-2) condensed at b. However, at least one of Z 1 and Z 2 is represented by the general formula (1-1).
L 1 has the same meaning as L 1 in Formula (1).
X 12 to X 14 are each independently a nitrogen atom, CH, or a carbon atom bonded to R 31 or L 1, and at least one of X 12 to X 14 is a nitrogen atom.
Y 11 to Y 13 each independently represent CH or a carbon atom bonded to R 31 or L 1 .
R 31 each independently represents a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number 3 30 to 30 alkylsilyl groups, substituted or unsubstituted arylsilyl groups having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted ring carbon atoms having 6 to 30 carbon atoms Or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms.
If R 31 there are a plurality, a plurality of R 31 may be the same or different from each other and, R 31 may be bonded to each other to form a ring adjacent.
k represents 1 or 2, and n represents an integer of 0 to 4.
C in the general formula (1-1) is condensed in a or b in the general formula (2);
Any one of d, e and f in the general formula (1-2) is condensed in a or b in the general formula (2). ]
The organic electroluminescence device according to claim 1, wherein the second host material is represented by the following general formula (3).

[Formula (3) Medium L 1 has the same meaning as L 1 in Formula (1).
X 12 to X 14 are each independently a nitrogen atom, CH, or a carbon atom bonded to R 31 or L 1, and at least one of X 12 to X 14 is a nitrogen atom.
Y 11 to Y 13 each independently represent CH or a carbon atom bonded to R 31 or L 1 .
R 31 each independently represents a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number 3 30 to 30 alkylsilyl groups, substituted or unsubstituted arylsilyl groups having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted ring carbon atoms having 6 to 30 carbon atoms Or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms.
If R 31 there are a plurality, a plurality of R 31 may be the same or different from each other and, R 31 may be bonded to each other to form a ring adjacent.
n represents an integer of 0 to 4.
R 41 to R 48 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted ring formation. A heterocyclic group having 5 to 30 atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms Group, substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or It represents an unsubstituted aralkyl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms.
Adjacent R 41 to R 48 may be bonded to each other to form a ring. ]
The organic electroluminescence device according to claim 1, wherein the first host material satisfies only the item (i).
The organic electroluminescence device according to claim 1, wherein the second host material is represented by the following general formula (4).

[In general formula (4),
L 1 has the same meaning as L 1 in Formula (1).
X 12 to X 14 are each independently a nitrogen atom, CH, or a carbon atom bonded to R 31 or L 1, and at least one of X 12 to X 14 is a nitrogen atom.
Y 11 to Y 13 each independently represent CH or a carbon atom bonded to R 31 or L 1 .
R 31 each independently represents a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number 3 30 to 30 alkylsilyl groups, substituted or unsubstituted arylsilyl groups having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted ring carbon atoms having 6 to 30 carbon atoms Or a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms.
If R 31 there are a plurality, a plurality of R 31 may be the same or different from each other and, R 31 may be bonded to each other to form a ring adjacent.
n represents an integer of 0 to 4.
L 2 and L 3 each independently represent a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted 2 to 5 ring atom having 2 to 30 ring atoms. A valent heterocyclic group, a cycloalkylene group having 5 to 30 ring carbon atoms, or a group in which these are connected is represented.
R 51 to R 54 each independently represents a halogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. A cyclic group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted group Alkylsilyl group having 3 to 30 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted ring carbon atoms It represents a 6-30 aralkyl group or a substituted or unsubstituted aryloxy group having 6-30 ring-forming carbon atoms.
If R 51 there are a plurality, a plurality of R 51 may be the same or different, and, R 51 may be bonded to each other to form a ring adjacent.
If R 52 there are a plurality, a plurality of R 52 may be the same or different, and, R 52 may be bonded to each other to form a ring adjacent.
If R 53 there are a plurality, a plurality of R 53 may be the same or different, and, R 53 may be bonded to each other to form a ring adjacent.
When a plurality of R 54 are present, the plurality of R 51 may be the same as or different from each other, and adjacent R 54 may be bonded to each other to form a ring.
M 2 represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
p and s each independently represent an integer of 0 to 4, and q and r each independently represents an integer of 0 to 3. ]
In Formula (A), at least one of A 1 and A 2 is substituted with a phenyl group substituted with a cyano group, a naphthyl group substituted with a cyano group, a phenanthryl group substituted with a cyano group, or a cyano group. Dibenzofuranyl group, dibenzothiophenyl group substituted with cyano group, biphenylyl group substituted with cyano group, terphenylyl group substituted with cyano group, 9,9-diphenylfluorenyl group substituted with cyano group A 9,9′-spirobi [9H-fluoren] -2-yl group substituted with a cyano group, a 9,9-dimethylfluorenyl group substituted with a cyano group, or a triphenylenyl group substituted with a cyano group The organic electroluminescent element according to claim 1.
The organic electroluminescence device according to claim 1, wherein the light emitting material contains a phosphorescent light emitting material which is an orthometalated complex of a metal atom selected from iridium (Ir), osmium (Os) and platinum (Pt).
The organic electroluminescence device according to claim 9, wherein an emission peak wavelength of the phosphorescent material is 490 nm or more and 700 nm or less.