JP2014216576A - Organic electroluminescent element and electronic device - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide an organic electroluminescent element which is driven at a low voltage and exhibits high efficiency, and to provide an electronic device including the organic electroluminescent element.SOLUTION: The organic electroluminescent element of the present invention includes an anode, a cathode provided facing the anode, and an organic layer provided between the anode and the cathode. The organic layer has a light-emitting layer, a first electron transport layer provided between the light-emitting layer and the cathode, and a second electron transport layer provided between the first electron transport layer and the cathode. The first electron transport layer contains a compound represented by general formula (1), and the second electron transport layer contains a compound represented by general formula (21).

Description

  The present invention relates to an organic electroluminescence element and an electronic apparatus.

Organic electroluminescence devices using organic substances (hereinafter sometimes abbreviated as “organic EL devices”) are promising for use as solid light-emitting, inexpensive, large-area full-color display devices, and many developments have been made. ing.
In general, an organic EL element includes a pair of counter electrodes and a light emitting layer disposed between the pair of electrodes. When an electric field is applied between both electrodes of the organic EL element, electrons are injected from the cathode side and holes are injected from the anode side. When the injected electrons and holes recombine in the light emitting layer, excitons are formed, and energy is released as light when returning from the excited state to the ground state. The organic EL element emits light based on such a principle.
Conventional organic EL elements have a higher driving voltage than inorganic light-emitting diodes. Further, the characteristic deterioration has been remarkably not put into practical use. Although recent organic EL elements have been gradually improved, lower voltage and higher efficiency are required.
Patent Document 1 describes an organic EL device having an electron transport layer containing a compound having a phenanthroline skeleton or a benzoquinoline skeleton and an organometallic complex.

JP 2010-27761 A

  However, although the lifetime of the organic EL element described in Patent Document 1 is improved as compared with the conventional organic EL element, the driving voltage and efficiency are about the conventional level, and further lower voltage and higher efficiency are required.

  An object of the present invention is to provide an organic electroluminescence device that is driven at a low voltage and exhibits high efficiency. Another object of the present invention is to provide an electronic device provided with the organic electroluminescence element.

An organic electroluminescence device according to an embodiment of the present invention includes an anode, a cathode provided to face the anode, and an organic layer provided between the anode and the cathode, wherein the organic layer is A light emitting layer, a first electron transport layer provided between the light emitting layer and the cathode,
A second electron transport layer provided between the first electron transport layer and the cathode, the first electron transport layer including a compound represented by the following general formula (1); The electron transport layer includes a compound represented by the following general formula (21).

[In the general formula (1),
X ¹ to X ⁶ are each independently a nitrogen atom, CR, CA, CR ¹¹ , or CR ¹² . However, at least one of X ¹ to X ⁶ is a nitrogen atom.
R is independently hydrogen atom, halogen atom, cyano group, nitro group, hydroxyl group, carboxyl group, sulfonyl group, mercapto group, substituted or unsubstituted boryl group, substituted or unsubstituted phosphino group, substituted or unsubstituted Substituted acyl group, substituted or unsubstituted amino group, substituted or unsubstituted silyl group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted Or an unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted ring forming carbon number 6 to 40 aryloxy groups, substituted or unsubstituted heteroaryloxy groups having 5 to 40 ring carbon atoms, substituted or unsubstituted Substituted alkylthio group having 1 to 30 carbon atoms, substituted or unsubstituted arylthio group having 6 to 40 ring carbon atoms, substituted or unsubstituted heteroarylthio group having 5 to 40 ring carbon atoms, substituted or unsubstituted An alkoxycarbonyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryloxycarbonyl group having 6 to 40 ring carbon atoms, a substituted or unsubstituted heteroaryloxycarbonyl group having 5 to 40 ring carbon atoms, substituted or unsubstituted It is selected from the group consisting of a substituted aromatic hydrocarbon group having 6 to 40 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 40 ring atoms.
R ¹¹ and R ¹² are each a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 40 ring atoms, or the following general formula It is group represented by (11).
A is represented by the following general formula (11).

(In the general formula (11),
a is an integer of 1 to 5.
L ¹ is a single bond or a linking group;
The linking group in L ¹ is a substituted or unsubstituted linear, branched or cyclic polyvalent aliphatic hydrocarbon group having 1 to 30 carbon atoms, a substituted or unsubstituted polyvalent amino group, substituted or Selected from an unsubstituted polyvalent aromatic hydrocarbon ring group having 6 to 40 ring carbon atoms, a substituted or unsubstituted polyvalent heterocyclic group having 5 to 40 ring atoms, and the above aromatic hydrocarbon ring group A divalent multiple linking group formed by bonding 2 to 3 groups, a divalent multiple linking group formed by bonding 2 to 3 groups selected from the heterocyclic group, or the aromatic group It is a divalent multiple linking group formed by bonding 2 to 3 groups selected from a hydrocarbon ring group and the heterocyclic group.
In the multiple linking group, the aromatic hydrocarbon ring group and the heterocyclic group constituting the multiple linking group may be the same or different from each other, and may be bonded to each other to form a ring. Good.
Ar ¹ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 40 ring atoms. When a is 2 or more and 5 or less, Ar ¹ is the same or different from each other.
Ar ¹ and L ¹ may or may not form a ring structure. ]]

(In the general formula (21),
b is an integer of 1 to 3.
Any one of R ²⁰¹ , R ²⁰² , R ^{206 to} R ²⁰⁹ is a single bond that binds to L ² .
R ²⁰¹ , R ²⁰² , and R ^{206 to} R ²⁰⁹ are the same as R in the general formula (1) except for a single bond bonded to L ² . Adjacent R ²⁰¹ , R ²⁰² , R ^{206 to} R ²⁰⁹ may or may not form a ring by bonding.
L ² is a single bond or a linking group that bonds one of R ²⁰¹ , R ²⁰² , R ^{206 to} R ²⁰⁹ to Ar ^2, and the linking group in L ² is a substituted or unsubstituted carbon number of 1 to 30 Linear, branched or cyclic divalent aliphatic hydrocarbon groups, substituted or unsubstituted ring-forming divalent aromatic hydrocarbon ring groups having 6 to 40 carbon atoms, substituted or unsubstituted ring formation A divalent heterocyclic group having 5 to 40 atoms, a divalent multiple linking group formed by bonding 2 to 3 groups selected from the aromatic hydrocarbon ring group, and 2 selected from the heterocyclic group A divalent multiple linking group formed by bonding from 1 to 3 groups, or a divalent multiple formed by bonding from 2 to 3 groups selected from the aromatic hydrocarbon ring group and the heterocyclic group It is a linking group.
In the multiple linking group, the aromatic hydrocarbon ring group and the heterocyclic group constituting the multiple linking group are the same or different from each other, and the adjacent aromatic hydrocarbon ring group and the heterocyclic group are a ring. May be formed or not formed.
Ar ² is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 40 ring atoms.
Ar ² and L ² may or may not form a ring structure.
However, Ar ² is a L ² is 9-position, and a bound anthracene ring at the 8-position from position 1 hydrogen atom, L ² is an aromatic substituted or unsubstituted having 6 to 40 ring carbon atoms carbide When R ²⁰² is a methyl group or an ethyl group, the atom or group bonded to the carbon atom at the 10-position of the anthracene ring is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a carboxyl group Group, sulfonyl group, mercapto group, substituted or unsubstituted boryl group, substituted or unsubstituted phosphino group, substituted or unsubstituted acyl group, substituted or unsubstituted amino group, substituted or unsubstituted silyl group, substituted or An 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 alkyl group having 2 to 30 carbon atoms; A alkynyl group, a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 40 ring carbon atoms, substituted or Unsubstituted heteroaryloxy group having 5 to 40 ring carbon atoms, substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, substituted or unsubstituted arylthio group having 6 to 40 ring carbon atoms, substituted or unsubstituted A heteroarylthio group having 5 to 40 ring carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryloxycarbonyl group having 6 to 40 ring carbon atoms, substituted or unsubstituted substituted ring-forming hetero aryloxy group having a carbon number of 5 to 40, a substituted or unsubstituted phenyl group F ^100, also substituted Ku is selected from the group consisting of heterocyclic group unsubstituted ring forming condensed aromatic hydrocarbon group F ¹⁰¹ carbon atoms 10 to 40, and substituted or unsubstituted ring atoms ^5-40.
However, when the substituent R ²⁰⁰ is bonded to the substituted or unsubstituted phenyl group F ¹⁰⁰ , the substituent R ²⁰⁰ is not an aromatic hydrocarbon group or a heterocyclic group. When the substituent R ²⁰¹ is bonded to the substituted or unsubstituted condensed aromatic hydrocarbon group F ¹⁰¹ having 10 to 40 ring carbon atoms, the substituent R ²⁰¹ is not an aromatic hydrocarbon group or a heterocyclic group. . )

  Meanwhile, an electronic apparatus according to an embodiment of the present invention includes the organic electroluminescence element according to an embodiment of the present invention.

  ADVANTAGE OF THE INVENTION According to this invention, the organic electroluminescent element which is driven with a low voltage and shows high efficiency can be provided. Moreover, the electronic device provided with the said organic electroluminescent element can be provided.

The figure which shows an example of the organic electroluminescent element which concerns on 1st embodiment of this invention. The figure which shows an example of the organic electroluminescent element which concerns on 2nd embodiment of this invention.

[Organic EL device]
(Element structure of organic EL element)
As typical element structures of the organic EL element in one embodiment of the present invention, for example, the following structures (a) to (e) can be mentioned.
(A) Anode / light emitting layer / cathode (b) Anode / hole injection / transport layer / light emitting layer / cathode (c) Anode / light emitting layer / electron injection / transport layer / cathode (d) Anode / hole injection / transport Layer / light emitting layer / electron injection / transport layer / cathode (e) anode / hole injection / transport layer / first light emitting layer / intermediate layer / second light emitting layer / electron injection / transport layer / cathode ) And (e) are preferably used, but of course not limited thereto.
The “light emitting layer” is an organic layer having a light emitting function, and 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 “hole injection / transport layer” means “at least one of a hole injection layer and a hole transport layer”, and “electron injection / transport layer” means “electron transport layer” or “electron injection layer”. "Layer and electron transport layer". Here, when it has a positive hole injection layer and a positive hole transport layer, it is preferable that the positive hole injection layer is provided in the anode side. Moreover, when it has an electron injection layer and an electron carrying layer, it is preferable that the electron injection layer is provided in the cathode side.

  The “intermediate layer” (also referred to as an intermediate conductive layer, a charge generation layer, or CGL) is a layer including at least one of the intermediate conductive layer and the charge generation layer, or at least one of the intermediate conductive layer and the charge generation layer. Yes, it becomes a source of electrons or holes injected into the light emitting unit. In addition to the electric charge injected from the pair of electrodes, the electric charge supplied from the intermediate layer is injected into the light emitting unit. Therefore, by providing the intermediate layer, the luminous efficiency (current efficiency) with respect to the injected current is increased. improves.

  An organic EL device according to an embodiment of the present invention includes a cathode, an anode, and an organic layer disposed between the cathode and the anode. The organic layer has at least a light emitting layer, a first electron transport layer, and a second electron transport layer, and further includes a hole injection layer, a hole transport layer, an electron injection layer, a hole barrier layer, an electron barrier layer, and the like. You may have the layer employ | adopted with an organic EL element. The organic layer may contain an inorganic compound.

<First embodiment>
As shown in FIG. 1, the organic EL element 1 according to the present embodiment includes a translucent substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4. Have.
The organic layer 10 includes a hole injection layer 6, a hole transport layer 7, a light emitting layer 5, a first electron transport layer 81, a second electron transport layer 82, and an electron injection layer 9 in order from the anode 3 side.

(First electron transport layer)
The first electron transport layer of the organic EL device 1 according to this embodiment includes a compound represented by the following general formula (1).

[In the general formula (1), X ¹ to X ⁶ are each independently a nitrogen atom, CR, CA, CR ¹¹ , or CR ¹² . However, at least one of X ¹ to X ⁶ is a nitrogen atom. R is independently hydrogen atom, halogen atom, cyano group, nitro group, hydroxyl group, carboxyl group, sulfonyl group, mercapto group, substituted or unsubstituted boryl group, substituted or unsubstituted phosphino group, substituted or unsubstituted Substituted acyl group, substituted or unsubstituted amino group, substituted or unsubstituted silyl group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted Or an unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted ring forming carbon number 6 to 40 aryloxy groups, substituted or unsubstituted heteroaryloxy groups having 5 to 40 ring carbon atoms, substituted or unsubstituted Substituted alkylthio group having 1 to 30 carbon atoms, substituted or unsubstituted arylthio group having 6 to 40 ring carbon atoms, substituted or unsubstituted heteroarylthio group having 5 to 40 ring carbon atoms, substituted or unsubstituted An alkoxycarbonyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryloxycarbonyl group having 6 to 40 ring carbon atoms, a substituted or unsubstituted heteroaryloxycarbonyl group having 5 to 40 ring carbon atoms, substituted or unsubstituted It is selected from the group consisting of a substituted aromatic hydrocarbon group having 6 to 40 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 40 ring atoms.
R ¹¹ and R ¹² are each a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 40 ring atoms, or the following general formula It is group represented by (11).
A is represented by the following general formula (11).

(In the general formula (11), a is an integer of 1 to 5.
L ¹ is a single bond or a linking group, and the linking group in L ¹ is a substituted or unsubstituted linear, branched or cyclic polyvalent aliphatic hydrocarbon group having 1 to 30 carbon atoms, a substituted group Or an unsubstituted polyvalent amino group, a substituted or unsubstituted polyvalent aromatic hydrocarbon ring group having 6 to 40 ring carbon atoms, a substituted or unsubstituted polyvalent complex having 5 to 40 ring atoms. A divalent multiple linking group formed by bonding 2 to 3 groups selected from a cyclic group, the aromatic hydrocarbon ring group, and 2 to 3 groups selected from the heterocyclic group Or a divalent multiple linking group formed by bonding two to three groups selected from the aromatic hydrocarbon ring group and the heterocyclic group.
In the multiple linking group, the aromatic hydrocarbon ring group and the heterocyclic group constituting the multiple linking group may be the same or different from each other, and may be bonded to each other to form a ring. Good.
Ar ¹ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 40 ring atoms. When a is 2 or more and 5 or less, Ar ¹ is the same or different from each other.
Ar ¹ and L ¹ may or may not form a ring structure. ]]

In the general formula (11), when L ¹ forms a multiple linking group and the heterocyclic group in the adjacent aromatic hydrocarbon ring group forms a ring, for example, when L ¹ is composed of three phenylene groups , And the following formulas (11a) and (11b).

In the general formula (11), Ar ¹ is preferably represented by the following general formula (12).

(In the general formula (12), X ¹¹ to X ¹⁸ are each independently a nitrogen atom and CR ^13. Z ¹ is an oxygen atom, a sulfur atom, NR ¹⁴ , CR ¹⁵ R ¹⁶ , SiR ¹⁷ R. ¹⁸ is a ^{.R 13} to ^{R 18} has the same meaning as R in the general formula (1).
However, any one of R ¹³ to R ¹⁸ is a single bond that bonds to L ¹ of the general formula (11).
If the formula (12) has a plurality of ^{R 13, R 13} are the same or different from each other.
Further, R ^{13 of} adjacent CR ¹³ may be bonded to each other to form a saturated or unsaturated ring. When Z ¹ is NR ¹⁴ , CR ¹⁵ R ¹⁶ , or SiR ¹⁷ R ¹⁸ , and at least one of X ¹¹ and X ¹⁸ is CR ¹³ , any one of R ¹⁴ to R ¹⁸ is one of R ¹³ may be bonded to each other to form a ring. Alternatively, Z ¹ may be directly bonded to one R ¹³ to form a ring.
In addition, R ¹³ to R ¹⁸ other than a single bond bonded to L ¹ may be further bonded to L ¹ of the general formula (11) to form a saturated or unsaturated ring. Good. )

In the general formula (12), when R ^{13s of} adjacent CR ¹³ are bonded to each other to form a saturated or unsaturated ring, for example, a ring represented by the following general formula (12A) or (12B) Form.

(In the general formula (12A), y ¹¹ and y ¹² represent bonding positions to two adjacent CR ¹³ in the general formula (12).
In the general formula (12B), y ¹³ and y ¹⁴ represent bonding positions to two adjacent CR ¹³ in the general formula (12).
X < ¹¹¹ > -X < ¹¹⁸ > is synonymous with X < ¹¹ > -X < ¹⁸ > in the said General formula (12), respectively.
Z ¹¹ has the same meaning as Z ¹ in the general formula (12). )

In the general formula (12), as examples in which R ^{13 of} adjacent CR ¹³ are bonded to each other to form a ring represented by the general formula (12A) or (12B), the following general formula (12A-1) ) To (12A-3) and the structures represented by the following general formulas (12B-1) to (12B-6).

(In the general formulas (12A-1) to (12A-3), Z ¹ , X ^{11 to} X ¹⁸ are synonymous with those of the general formula (12), and X ^{111 to} X ¹¹⁴ are it is synonymous with ^X 11 ^{to X 18} in 12).)

(In the general formulas (12B-1) to (12B-6), Z ¹ , X ^{11 to} X ¹⁸ are synonymous with those in the general formula (12), and Z ¹¹ is the same in the general formula (12). Z ¹ is synonymous with X ¹ and X ^{115 to} X ¹¹⁸ are synonymous with X ^{11 to} X ¹⁸ in the general formula (12).

Further, the above general formula ^{(12), X 13} or ^{X 16} is a ^{CR 13,} preferably a single ^{bond R 13} is bonded to ^{L 1.}
In the general formula (12), Z ¹ is preferably an oxygen atom or NR ¹⁴ , and more preferably NR ¹⁴ .
In the general formula (12), it is preferable that Z ¹ is NR ¹⁴ and X ¹¹ to X ¹⁸ are CR ¹³ . That is, in the general formula (11), Ar ¹ is preferably a substituted or unsubstituted carbazolyl group.
In the general formula (12), Z ¹ is NR ¹⁴ , X ¹¹ to X ¹⁸ are CR ¹³ , and R ¹⁴ is a single bond bonded to L ¹ in the general formula (11). Is also preferable.

In the general formula (11), Ar ¹ is preferably a substituted or unsubstituted condensed aromatic hydrocarbon group having 8 to 20 ring carbon atoms.
The condensed aromatic hydrocarbon group having 8 to 20 ring carbon atoms is preferably a group derived from naphthalene, anthracene, acephenanthrylene, acanthrylene, benzoanthracene, triphenylene, pyrene, chrysene or naphthacene.

In the general formula (11), Ar ¹ is preferably a group represented by the following general formula (13).

(In the general formula (13), the bond represents a single bond bonded from any carbon atom to L ¹ in the general formula (11).)

In the general formula (11), Ar ¹ is preferably a group represented by the following general formula (14).

(In the general formula (14), t represents an integer of 1 to 3, n represents an integer of 1 to 4. R ¹¹¹ has the same meaning as R in the general formula (1); The plurality of R ¹¹¹ are the same or different from each other, and L ¹¹ and L ¹² have the same meaning as L ^{1 in the} general formula (11).
Ar ¹² is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 40 ring atoms.
L ¹¹ is single-bonded to L ¹ in the general formula (11). A plurality of R ¹¹¹ are each bonded to any carbon atom of the carbazolyl group, and the two carbazolyl groups are bonded to each other at any position from the 1st position to the 4th position. )

In the general formula (11), a is preferably an integer of 1 or more and 3 or less, and a is more preferably 1 or 2.
In the general formula (11), a is 1, L ¹ is a linking group, and the linking group in L ¹ is a substituted or unsubstituted divalent aromatic hydrocarbon having 6 to 40 ring carbon atoms. Or a substituted or unsubstituted divalent heterocyclic group having 5 to 40 ring atoms.
In the general formula (11), a is 2, L ¹ is a linking group, and the linking group in L ¹ is a substituted or unsubstituted trivalent aromatic having 6 to 40 ring carbon atoms. A hydrocarbon group or a substituted or unsubstituted trivalent heterocyclic group having 5 to 40 ring atoms is also preferable.

Further, in the general formula (11), L ¹ is preferably a divalent or trivalent residue derived from any one of benzene, biphenyl, terphenyl, naphthalene, and phenanthrene.

  The general formula (1) is preferably represented by the following general formula (100).

(In the general formula (100), X ¹ , X ³ and X ⁵ are each independently a nitrogen atom or CR, provided that at least one of X ¹ , X ³ and X ⁵ is a nitrogen atom. .
^{A, R,} R ^{11, R 12} is an ^A in each of the general formula ^{(1), R,} and R ^{11, R 12} synonymous. )

In the general formula (1), it is preferable that any two or three of X ¹ to X ⁶ are nitrogen atoms. Among them, in the general formula (1), it is preferable that any two or three of X ¹ , X ³ and X ⁵ are nitrogen atoms, that is, in the general formula (100), X ¹ , X ³ or X ⁵ is preferably a nitrogen atom.

And it is especially preferable that the general formula (1) is represented by the following general formulas (1A) to (1D). That is, in the case of pyrimidine in which X ¹ and X ³ are nitrogen atoms, in the case of pyrimidine in which X ³ and X ⁵ are nitrogen atoms, in the case of pyrimidine in which X ¹ and X ⁵ are nitrogen atoms, and X ¹ , X ³ and X ⁵ are preferably triazines each having a nitrogen atom.

In the general formula (1), R ¹¹ or R ¹² is preferably a group selected from the group consisting of the following formulas (1a) to (1p).

In the general formula (1), X ¹ and X ³ are nitrogen atoms, X ⁴ is CR ¹² , and R ¹² is a group selected from the group consisting of the above formulas (1a) to (1p). It is preferable. That is, it is preferable that the general formula (1) is represented by the general formula (1A), and R ¹² is a group selected from the group consisting of the above formulas (1a) to (1p).

  As such a compound represented by the general formula (1), a compound represented by the following general formula (1-1) is preferable, and a compound represented by the following general formula (1-2) is more preferable. As the compound represented by the general formula (1), a compound represented by the following general formula (1-3) is further preferable, and a compound represented by the following general formula (1-4) is particularly preferable.

(In the general formula ^{(1-1), R 11} is .L ¹ and ^{L 121} are the same meaning as ^{R 11} in the formula (1) has the same meaning as ^{L 1} in the general formula (11) .a Is synonymous with a in the general formula (11), Ar ¹²¹ is synonymous with Ar ¹ in the general formula (11), and Z ¹ , X ^{11 to} X ¹⁸ are respectively the general formula (12). L ¹ is bonded to Z ¹ and any ^one of X ^{11 to} X ¹⁸ .

(In the general formula ^{(1-2), R 11} is .L ¹ and ^{L 121} are the same meaning as ^{R 11} in the formula (1) has the same meaning as ^{L 1} in the general formula (11), a is synonymous with a in the general formula (11), Ar ¹²¹ is synonymous with Ar ¹ in the general formula (11), and Cz is a group represented by the following general formula (1-21). .)

(In General Formula (1-21), R ¹⁰¹ is independently synonymous with R ¹³ in General Formula (12), and R ¹⁰² is synonymous with R ¹⁴ in General Formula (12). c is an integer of 1 to 8. When c is 2 or more, the plurality of R ¹⁰¹ are the same or different from each other.
However, at least one of R ¹⁰¹ and R ¹⁰² is a single bond that bonds to L ¹ in the general formula (1-2). R ¹⁰¹ is bonded to any carbon atom of the carbazolyl group. )

(In the general formula (1-3), R ¹¹ , L ¹²¹ , Ar ¹²¹ , and Cz have the same meanings as those in the general formula (1-2). Note that Cz and the pyrimidine ring are benzene rings. Bonded to any carbon atom.)

(In the general formula (1-4), R ¹¹ , L ¹²¹ , Ar ¹²¹ , and Cz have the same meanings as those in the general formula (1-2). R ¹⁰¹ and c each represent the general formula ( The carbazolyl group and the pyrimidine ring are bonded to any carbon atom of the benzene ring, and R ¹⁰¹ is bonded to any carbon atom of the carbazolyl group. )

In the general formula (1-4), more preferably, R ¹⁰¹ is a hydrogen atom, and R ¹¹ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 ring carbon atoms. More preferably, R ¹¹ is a substituted or unsubstituted phenyl group, and particularly preferably an unsubstituted phenyl group.

Furthermore, in the general formula (1-4), -L ¹²¹ -Ar ¹²¹ is preferably any one of the formulas (1a) to (1p).

  Next, the general formulas (1), (1A) to (1D), (1-1) to (1-4), (1-21) (11), (12), (12A), (12B), Each substituent described in (12A-1) to (12A-3), (12B-1) to (12B-6), (14), and (100) will be described. The general formulas (1), (1A) to (1D), (1-1) to (1-4), (1-21) (11), (12), (12A), (12B), (12A -1) to (12A-3), (12B-1) to (12B-6), (14), and (100) include, for example, a halogen atom, a cyano group, a nitro group, a hydroxyl group. Group, carboxyl group, sulfonyl group, mercapto group, substituted or unsubstituted boryl group, substituted or unsubstituted phosphino group, substituted or unsubstituted acyl group, substituted or unsubstituted amino group, substituted or unsubstituted silyl 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 carbon number 6-30 Aralkyl group, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 40 ring carbon atoms, substituted or unsubstituted heteroaryloxy having 5 to 40 ring carbon atoms A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 40 ring carbon atoms, a substituted or unsubstituted heteroarylthio group having 5 to 40 ring carbon atoms, Substituted or unsubstituted alkoxycarbonyl group having 2 to 30 carbon atoms, substituted or unsubstituted aryloxycarbonyl group having 6 to 40 ring carbon atoms, substituted or unsubstituted heteroaryloxycarbonyl having 5 to 40 ring carbon atoms Group, substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 ring carbon atoms, and substituted or unsubstituted ring forming atom And a heterocyclic group 5-40.

  The general formulas (1), (1-1) to (1-4), (1-21) (11), (12), (12A), (12B), (12A-1) to (12A-3) ), (12B-1) to (12B-6), (14), (100) include fluorine, chlorine, bromine, iodine, etc., preferably fluorine.

The general formulas (1), (1-1) to (1-4), (1-21) (11), (12), (12A), (12B), (12A-1) to (12A-3) ), (12B-1) to (12B-6), (14), (100) include a boryl group (—BH ₂ ), a boryl group (—BH ₂ ), and a boryl group (—BH ₂ ). H also includes groups represented as ^{R E, -BR} E ^R E which is optionally substituted with ^{R E.}
Here, when R ^E is an alkyl group, it becomes an alkylboryl group, and a substituted or unsubstituted alkylboryl group is preferable. The alkyl group as R ^E is preferably the following alkyl group having 1 to 30 carbon atoms.
Further, when R ^E is an aryl group, it becomes an arylboryl group, and a substituted or unsubstituted arylboryl group is preferable. The aryl group as R ^E is preferably the following aromatic hydrocarbon group having 6 to 40 ring carbon atoms.
Further, when R ^E is a heteroaryl group, it becomes a heteroarylboryl group, and a substituted or unsubstituted heteroarylboryl group is preferable. The heteroaryl group as R ^E is preferably the following heterocyclic group having 5 to 40 ring atoms.
In addition, a dihydroxyboryl group (-B (OH) ₂ ) is mentioned.

The general formulas (1), (1-1) to (1-4), (1-21) (11), (12), (12A), (12B), (12A-1) to (12A-3) ), (12B-1) to (12B-6), (14), (100), the substituted or unsubstituted phosphino group includes a group represented by a phosphino group (—PH ₂ ), a phosphino group ( H of -PH ₂₎ is ^R F, or a group represented as ^-PR F ^{R F} substituted with ^{R F,} also a group represented as -P ^{(O) R F} R F contains.
Here, when R ^F is an alkyl group, it becomes an alkyl phosphino group, and a substituted or unsubstituted alkyl phosphino group is preferable. The alkyl group as R ^F is preferably the following alkyl group having 1 to 30 carbon atoms.
Further, when R ^F is an aryl group, it becomes an aryl phosphino group, and a substituted or unsubstituted aryl phosphino group is preferable. The aryl group as R ^F is preferably the following aromatic hydrocarbon group having 6 to 40 ring carbon atoms.
In addition, when R ^F is a heteroaryl group, it becomes a heteroaryl phosphino group, and a substituted or unsubstituted heteroaryl phosphino group is preferable. The heteroaryl group as R ^F is preferably the following heterocyclic group having 5 to 40 ring atoms.

The general formulas (1), (1-1) to (1-4), (1-21) (11), (12), (12A), (12B), (12A-1) to (12A-3) ), (12B-1) to (12B-6), (14), (100), the substituted or unsubstituted acyl group is represented by -CO- ^RD .
Here, when ^RD is an alkyl group, it becomes an alkylcarbonyl group, and a substituted or unsubstituted alkylcarbonyl group having 2 to 30 carbon atoms is preferable. The alkyl group as ^RD is preferably the following alkyl group having 1 to 30 carbon atoms. Specific examples of the alkylcarbonyl group include an acetyl group, a propionyl group, a butyryl group, a valeryl group, a pivaloyl group, a palmitoyl group, a stearoyl group, and an oleoyl group.
Further, when ^RD is an aryl group, it becomes an arylcarbonyl group (sometimes referred to as an aroyl group), and a substituted or unsubstituted arylcarbonyl group having 6 to 40 ring carbon atoms is preferable. The aryl group as ^RD is preferably the following aromatic hydrocarbon group having 6 to 40 ring carbon atoms. Specific examples of the arylcarbonyl group include a benzoyl group, a toluoyl group, a salicyloyl group, a cinnamoyl group, a naphthoyl group, and a phthaloyl group.
Further, when ^RD is a heteroaryl group, it becomes a heteroarylcarbonyl group, which is preferably a substituted or unsubstituted heteroarylcarbonyl group having 5 to 40 ring atoms. The heteroaryl group as ^RD is preferably the following heterocyclic group having 5 to 40 ring atoms. Specific examples of the heteroarylcarbonyl group include a furoyl group, a pyrrolylcarbonyl group, a pyridylcarbonyl group, and a thienylcarbonyl group.
In addition, the formyl group (—CO—H) in which ^RD is a hydrogen atom is also included in the acyl group referred to herein.

The general formulas (1), (1-1) to (1-4), (1-21) (11), (12), (12A), (12B), (12A-1) to (12A-3) ), (12B-1) to (12B-6), (14), (100), the substituted or unsubstituted amino group includes an amino group (—NH ₂ ) and an amino group (—NH ₂ ). Examples include amino groups in which H is substituted with each substituent. For example, an alkylamino group substituted with a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group substituted with an aryl group having 6 to 40 ring carbon atoms, substituted or unsubstituted And a heteroarylamino group substituted with a heteroaryl group having 5 to 40 ring atoms and an acylamino group substituted with a substituted or unsubstituted acyl group having 2 to 30 carbon atoms.
The alkyl group having 1 to 30 carbon atoms in the alkylamino group is preferably the following alkyl group having 1 to 30 carbon atoms. When substituted with two alkyl groups, the two alkyl groups may be the same or different.
The aryl group having 6 to 40 ring carbon atoms in the arylamino group is preferably the following aromatic hydrocarbon group having 6 to 40 ring carbon atoms. The arylamino group is preferably an amino group substituted with a phenyl group. When substituted with two aryl groups, the two aryl groups may be the same or different.
The heteroaryl group having 5 to 40 ring atoms in the heteroarylamino group is preferably the following heterocyclic group having 5 to 40 ring atoms. When substituted with two heteroaryl groups, the two heteroaryl groups may be the same or different.
The acyl group having 2 to 30 carbon atoms in the acylamino group is preferably selected from the acyl groups.
In addition, the substituted amino group may be one selected from a hydrogen atom, an alkyl group, an aryl group, a heteroaryl group and an acyl group and substituted.
For example, it may be an amino group in which an alkyl group and an aryl group are substituted, and examples thereof include an alkylarylamino group, an alkylheteroarylamino group, an arylheteroarylamino group, an alkylacylamino group, and an arylacylamino group.

The general formulas (1), (1-1) to (1-4), (1-21) (11), (12), (12A), (12B), (12A-1) to (12A-3) ), (12B-1) to (12B-6), (14), (100), the substituted or unsubstituted silyl group includes, for example, an unsubstituted silyl group, for example, a substituted or unsubstituted carbon number of 1 An alkylsilyl group substituted with an alkyl group of ˜30, a substituted or unsubstituted arylsilyl group substituted with an aryl group of 6 to 40 ring carbon atoms, a substituted or unsubstituted heterocycle having 5 to 40 ring atoms And heteroarylsilyl group substituted with an aryl group.
Examples of the alkylsilyl group include a trialkylsilyl group having an alkyl group having 1 to 30 carbon atoms, specifically, a trimethylsilyl group, a triethylsilyl group, a tri-n-butylsilyl group, and a tri-n-octylsilyl group. , Triisobutylsilyl group, dimethylethylsilyl group, dimethylisopropylsilyl group, dimethyl-n-propylsilyl group, dimethyl-n-butylsilyl group, dimethyl-t-butylsilyl group, diethylisopropylsilyl group, vinyldimethylsilyl group, propyldimethyl A silyl group, a triisopropylsilyl group, etc. are mentioned. The three alkyl groups may be the same or different from each other.
Examples of the arylsilyl group include triarylsilyl groups having the following three aromatic hydrocarbon groups having 6 to 40 ring carbon atoms, and the triarylsilyl group preferably has 18 to 30 carbon atoms. The three aryl groups may be the same or different from each other.
Examples of the heteroarylsilyl group include triheteroarylsilyl groups having the following three heterocyclic groups having 5 to 40 ring atoms. The three heteroaryl groups may be the same or different from each other.
Further, as the substituted silyl group, at least two kinds selected from an alkyl group, an aryl group and a heteroaryl group may be substituted.
For example, it may be a silyl group in which an alkyl group and an aryl group are substituted, and examples thereof include an alkylarylsilyl group, a dialkylarylsilyl group, a diarylsilyl group, an alkyldiarylsilyl group, and a triarylsilyl group. A plurality of aryl groups or alkyl groups may be the same or different.
The dialkylarylsilyl group has, for example, two alkyl groups exemplified by the above alkyl group having 1 to 30 carbon atoms, and one dialkylarylsilyl group having one aromatic hydrocarbon group having 6 to 40 ring carbon atoms below. Is mentioned. The carbon number of the dialkylarylsilyl group is preferably 8-30. The two alkyl groups may be the same or different.
Examples of the alkyldiarylsilyl group include an alkyldiarylsilyl group having one alkyl group exemplified for the alkyl group having 1 to 30 carbon atoms and two aryl groups having 6 to 40 ring carbon atoms. . The alkyldiarylsilyl group preferably has 13 to 30 carbon atoms. The two aryl groups may be the same or different.
Examples of such an arylsilyl group include a phenyldimethylsilyl group, a diphenylmethylsilyl group, a diphenyl-t-butylsilyl group, and a triphenylsilyl group.
Further, a silyl group in which an alkyl group and a heteroaryl group are substituted, a silyl group in which an aryl group and a heteroaryl group are substituted, or a silyl group in which an alkyl group, an aryl group, and a heteroaryl group are substituted Good.

The general formulas (1), (1-1) to (1-4), (1-21) (11), (12), (12A), (12B), (12A-1) to (12A-3) ), (12B-1) to (12B-6), (14), (100), the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms may be linear, branched or cyclic. Also good. The substituted alkyl group having 1 to 30 carbon atoms includes a haloalkyl group. Examples of the haloalkyl group include those in which the alkyl group having 1 to 30 carbon atoms is substituted with one or more halogen atoms. Examples of the substituted or unsubstituted linear or branched alkyl group include, for example, methyl group, ethyl group, 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, 2-methylpentyl group, 1-pentylhexyl group, 1-butylpentyl group, 1-heptyloctyl group , 3-methylpentyl group, hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 2-hydroxyisobutyl group, 1, -Dihydroxyethyl group, 1,3-dihydroxyisopropyl group, 2,3-dihydroxy-t-butyl group, 1,2,3-trihydroxypropyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2 -Chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo-t-butyl group, 1,2,3-tribromopropyl group, iodomethyl Group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodo Sopropyl group, 2,3-diiodo-t-butyl group, 1,2,3-triiodopropyl group, aminomethyl group, 1-aminoethyl group, 2-aminoethyl group, 2-aminoisobutyl group, 1,2 -Diaminoethyl group, 1,3-diaminoisopropyl group, 2,3-diamino-t-butyl group, 1,2,3-triaminopropyl group, cyanomethyl group, 1-cyanoethyl group, 2-cyanoethyl group, 2- Cyanoisobutyl group, 1,2-dicyanoethyl group, 1,3-dicyanoisopropyl group, 2,3-dicyano-t-butyl group, 1,2,3-tricyanopropyl group, nitromethyl group, 1-nitroethyl group, 2-nitroethyl group, 1,2-dinitroethyl group, 2,3-dinitro-t-butyl group, 1,2,3-trinitropropyl group, fluoromethyl group, difluorome A til group, a trifluoromethyl group, a fluoroethyl group, a 2,2,2-trifluoroethyl group, a 1,1,1,3,3,3-hexafluoro-2-propyl group and the like can be mentioned.
The substituted or unsubstituted cyclic alkyl group (cycloalkyl group) is preferably a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cyclopentyl group. Cyclohexyl group, cyclooctyl group, 4-methylcyclohexyl group, 3,5-tetramethylcyclohexyl group, 1-adamantyl group, 2-adamantyl group, 1-norbornyl group, 2-norbornyl group and the like.
Among the above alkyl groups, an alkyl group having 1 to 10 carbon atoms is preferable, an alkyl group having 1 to 8 carbon atoms is more preferable, and an alkyl group having 1 to 6 carbon atoms is particularly preferable. Of these, a methyl group, an isopropyl group, a t-butyl group, and a cyclohexyl group are preferable.

  The general formulas (1), (1-1) to (1-4), (1-21) (11), (12), (12A), (12B), (12A-1) to (12A-3) ), (12B-1) to (12B-6), (14), (100), the substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms may be linear, branched or cyclic. For example, vinyl group, propenyl group, butenyl group, oleyl group, eicosapentaenyl group, docosahexaenyl group, styryl group, 2,2-diphenylvinyl group, 1,2,2-triphenylvinyl group, A 2-phenyl-2-propenyl group and the like can be mentioned. Among the alkenyl groups described above, a vinyl group is preferable.

  The general formulas (1), (1-1) to (1-4), (1-21) (11), (12), (12A), (12B), (12A-1) to (12A-3) ), (12B-1) to (12B-6), (14), (100), examples of the substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms include ethynyl, propynyl, 2-phenylethynyl and the like. Can be mentioned. Of the alkynyl groups described above, an ethynyl group is preferred.

The general formulas (1), (1-1) to (1-4), (1-21) (11), (12), (12A), (12B), (12A-1) to (12A-3) ), (12B-1) to (12B-6), (14), (100), the aralkyl group having 7 to 40 carbon atoms is represented as -R ^E -R ^F. The examples of R ^E, include alkylene groups and divalent alkyl groups of 1 to 30 carbon atoms. Examples of R ^F, is, for example, the aromatic hydrocarbon group below having 6 to 40 ring carbon atoms. In this aralkyl group, the aryl group moiety has 6 to 40 carbon atoms, preferably 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms. Moreover, in this aralkyl group, the alkyl group moiety has 1 to 30, preferably 1 to 20, more preferably 1 to 10, and further preferably 1 to 6 carbon atoms. Examples of the aralkyl group include benzyl group, 2-phenylpropan-2-yl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, and 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-chlorobenzyl group, o-chlorobenzyl group, p-bromine Benzyl 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.

The general formulas (1), (1-1) to (1-4), (1-21) (11), (12), (12A), (12B), (12A-1) to (12A-3) ), (12B-1) to (12B-6), (14), (100), a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 ring carbon atoms heteroaryloxy groups oxy group and a substituted or unsubstituted ring formed from 5 to 40 carbon atoms is represented by -OR ^a.
Here, when R ^A is an alkyl group, it becomes an alkoxy group, and a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms is preferable. The alkyl group as R ^A is preferably the alkyl group having 1 to 30 carbon atoms. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, and a hexyloxy group. Among the alkoxy groups, an alkoxy group having 1 to 10 carbon atoms is preferable, and an alkoxy group having 1 to 8 carbon atoms is more preferable. Particularly preferred is an alkoxy group having 1 to 4 carbon atoms.
The substituted or unsubstituted alkoxy group herein includes a haloalkoxy group in which an alkyl group as R ^A is substituted with one or more halogen atoms.
Moreover, when ^RA is an aryl group, it becomes an aryloxy group, and a substituted or unsubstituted aryloxy group having 6 to 40 ring carbon atoms is preferable. The aryl group as R ^A is preferably the following aromatic hydrocarbon group having 6 to 40 ring carbon atoms. Examples of the aryloxy group include a phenoxy group.
The substituted or unsubstituted aryloxy group referred to herein includes a haloaryloxy group in which the aryl group as R ^A is substituted with one or more halogen atoms.
Further, when R ^A is a heteroaryl group, it becomes a heteroaryloxy group, preferably a substituted or unsubstituted heteroaryloxy group having 5 to 40 ring atoms. The heteroaryl group as R ^A is preferably the following heterocyclic group having 5 to 40 ring atoms.

The general formulas (1), (1-1) to (1-4), (1-21) (11), (12), (12A), (12B), (12A-1) to (12A-3) ), (12B-1) to (12B-6), (14), (100), a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio having 6 to 40 ring carbon atoms. heteroarylthio groups and substituted or unsubstituted ring formed from 5 to 40 carbon atoms is represented by -SR ^C.
Here, when R ^C is an alkyl group, it becomes an alkylthio group, and a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms is preferable. The alkyl group as R ^C is preferably the alkyl group having 1 to 30 carbon atoms.
Further, when R ^C is an aryl group, it becomes an arylthio group, and a substituted or unsubstituted arylthio group having 6 to 40 ring carbon atoms is preferable. The aryl group as R ^C is preferably the following aromatic hydrocarbon group having 6 to 40 ring carbon atoms.
Further, when R ^C is a heteroaryl group, it becomes a heteroarylthio group, which is preferably a substituted or unsubstituted heteroarylthio group having 5 to 40 ring atoms. The heteroaryl group as R ^C is preferably the following heterocyclic group having 5 to 40 ring atoms.

The general formulas (1), (1-1) to (1-4), (1-21) (11), (12), (12A), (12B), (12A-1) to (12A-3) ), (12B-1) to (12B-6), (14), (100), a substituted or unsubstituted heteroarylcarbonyl group having 6 to 40 ring carbon atoms, a substituted or unsubstituted carbon number of 2 to 30 The alkoxycarbonyl group, the substituted or unsubstituted aryloxycarbonyl group having 6 to 40 ring carbon atoms and the substituted or unsubstituted heteroaryloxycarbonyl group having 5 to 40 ring carbon atoms are represented by -COOR ^B. .
Here, R ^B is the alkyl group, it is an alkoxycarbonyl group, an alkoxycarbonyl group having a substituted or unsubstituted 2 to 30 carbon atoms are preferred. The alkyl group as R ^B is an alkyl group of the 1 to 30 carbon atoms are preferred.
Further, when R ^B is an aryl group, it becomes an aryloxycarbonyl group, and a substituted or unsubstituted aryloxycarbonyl group having 7 to 40 carbon atoms is preferable. Aryl group of R ^B is preferably an aromatic hydrocarbon group below having 6 to 40 ring carbon atoms.
Further, when R ^B is a heteroaryl group, it becomes a heteroaryloxycarbonyl group, preferably a substituted or unsubstituted heteroaryloxycarbonyl group having 5 to 40 ring atoms. The heteroaryl group as R ^B is preferably the following heterocyclic group having 5 to 40 ring atoms.

  The general formulas (1), (1A) to (1D), (1-1) to (1-4), (1-21) (11), (12), (12A), (12B), (12A -1) to (12A-3), (12B-1) to (12B-6), (14), (100) as the aromatic hydrocarbon group having 6 to 40 ring carbon atoms, non-condensed aromatic And hydrocarbon group and condensed aromatic hydrocarbon group. More specifically, phenyl group, naphthyl group, anthryl group, phenanthryl group, biphenyl group, terphenyl group, quarterphenyl group, fluoranthenyl group, pyrenyl group , Triphenylenyl group, phenanthrenyl group, fluorenyl group, 9,9-dimethylfluorenyl group, spirofluorenyl group, benzo [c] phenanthrenyl group, benzo [a] triphenylenyl group, naphtho [1,2-c] Enantoreniru group, naphtho [1,2-a] triphenylenyl group, dibenzo [a, c] triphenylenyl group, benzo [b] fluoranthenyl group, and the like. Among the above aromatic hydrocarbon groups, an aromatic hydrocarbon group having 6 to 30 ring carbon atoms is more preferable, an aromatic hydrocarbon group having 6 to 20 ring carbon atoms is more preferable, and an aromatic hydrocarbon group having 6 to 12 ring carbon atoms is more preferable. The aromatic hydrocarbon group is particularly preferred.

  The general formulas (1), (1A) to (1D), (1-1) to (1-4), (1-21) (11), (12), (12A), (12B), (12A -1) to (12A-3), (12B-1) to (12B-6), (14), (100) as the heterocyclic group having 5 to 40 ring atoms, a non-fused heterocyclic group and A fused heterocyclic group, and more specifically, pyrrolyl group, pyrazinyl group, pyridinyl group, indolyl group, isoindolyl group, furyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, dibenzothiophenyl group Quinolyl group, isoquinolyl group, quinoxalinyl group, carbazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, thienyl group, and pyridine ring, pyrazine ring, pyrimidine ring, pyridazine ring, Liazine 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 And groups formed from a ring, a thiadiazole ring, a benzothiazole ring, a triazole ring, an imidazole ring, a benzimidazole ring, a pyran ring, a dibenzofuran ring, a benzo [c] dibenzofuran ring, and a silafluorene ring. Among the heterocyclic groups, a heterocyclic group having 5 to 40 ring atoms is more preferable, a heterocyclic group having 5 to 20 ring atoms is more preferable, and a heterocyclic group having 5 to 12 ring atoms is particularly preferable. preferable.

In the general formulas (11), (14), (1-1) to (1-4), L ¹ , L ¹¹ , L ¹² , and L ¹²¹ are polyvalent polyvalent groups having 1 to 30 carbon atoms. Examples of the linear, branched or cyclic aliphatic hydrocarbon group include the above-described polyvalent linear, branched or cyclic alkyl groups having 1 to 30 carbon atoms, and many carbon atoms having 1 to 30 carbon atoms. Valent linear, branched or cyclic alkenyl groups, polyvalent straight chain having 1 to 30 carbon atoms, or branched alkynyl groups having a polyvalent group. A trivalent group is preferred, and a divalent group is more preferred. These divalent groups may have the aforementioned substituent. Specific examples include a methylene group, an ethylene group, an acetylenylene group, and a vinylidene group.
When L ¹ , L ¹¹ , L ¹² , and L ^{121 in the} general formulas (11), (14), and (1-1) to (1-4) are linking groups, the number of ring forming carbon atoms is 6 to 40 Examples of the valent aromatic hydrocarbon group include those having the above-mentioned aromatic hydrocarbon group having 6 to 40 ring carbon atoms as a polyvalent group, preferably a divalent or trivalent group. Groups are more preferred. Specifically, a phenyl group, a biphenyl group, a naphthyl group, or a 9,9-dimethylfluorenyl group as a divalent group is preferable, and these divalent groups may have the above-described substituents. Good.
When L ¹ , L ¹¹ , L ¹² , and L ^{121 in the} general formulas (11), (14), and (1-1) to (1-4) are linking groups, the number of ring-forming atoms is 5 to 40 Examples of the valent heterocyclic group include those in which the aforementioned heterocyclic group having 5 to 40 ring atoms is a polyvalent group, preferably a divalent or trivalent group, and more preferably a divalent group. . Specifically, a pyridyl group, a pyrimidyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a silafluorenyl group, and a carbazolyl group are preferable, and these divalent groups have the above-described substituents. It may be.

Of X ^{11 to} X ¹⁸ in the general formula (12), in addition to the carbon atom bonded to L ¹ , CR ^Y is preferable, and R ^Y is more preferably a hydrogen atom or an alkyl group. A hydrogen atom is preferable, and a hydrogen atom is particularly preferable.

In the present invention, “ring-forming carbon” means a carbon atom constituting a saturated ring, an unsaturated ring, or an aromatic ring. “Ring-forming atom” means a carbon atom and a hetero atom constituting a hetero ring (including a saturated ring, an unsaturated ring, and an aromatic ring).
In the present invention, the hydrogen atom includes isotopes having different numbers of neutrons, that is, light hydrogen (Protium), deuterium (Deuterium), and tritium (Tritium).

In the case of “substituted or unsubstituted”, examples of the substituent include an aryl group, a heteroaryl group, an alkyl group (a linear or branched alkyl group, a cycloalkyl group, a haloalkyl group), and an alkoxy group as described above. , Aryloxy group, aralkyl group, haloalkoxy group, alkylsilyl group, dialkylarylsilyl group, alkyldiarylsilyl group, triarylsilyl group, halogen atom, cyano group, hydroxyl group, nitro group, and carboxy group. In addition, an alkenyl group and an alkynyl group are also included.
Among the substituents listed here, aryl groups, heteroaryl groups, alkyl groups, halogen atoms, alkylsilyl groups, arylsilyl groups, and cyano groups are preferable, and specific examples that are preferable in the description of each substituent Are preferred.
The term “unsubstituted” in the case of “substituted or unsubstituted” means that a hydrogen atom is bonded without being substituted with the substituent.

Note that in this specification, the number of ring-forming carbons refers to a compound having a structure in which atoms or molecules are bonded in a ring (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a spiro ring compound, a carbocyclic compound, or a heterocyclic compound). ) Represents the number of carbon atoms among the atoms constituting the ring itself. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring-forming carbons. The “ring-forming carbon number” in the present specification is the same unless otherwise specified.
In addition, the number of ring-forming atoms is determined by the ring itself of a compound having a structure in which atoms or molecules are bonded in a ring (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a spiro ring compound, a carbocyclic compound, or a heterocyclic compound). Represents the number of constituent atoms. For example, atoms that do not constitute a ring, such as hydrogen atoms bonded to atoms that constitute a ring, and atoms included in a substituent when the ring is substituted by a substituent are not included in the number of ring-forming atoms. For example, the benzene ring has 6 ring-forming carbon atoms, and the naphthalene ring has 10 ring-forming carbon atoms. The “ring-forming carbon number” in the present specification is the same unless otherwise specified.
The number of carbon atoms of the substituent does not include the carbon of the mother nucleus to which the substituent is bonded, or the carbon in the substituent when the substituent is further substituted. Moreover, when forming a ring with adjacent substituents, the said ring is cut | disconnected so that it may become a structure where carbon number of any substituent is in the said carbon number range, and it is set as carbon number of each substituent. The “substituent carbon number” in this specification is the same unless otherwise specified.

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

In the organic EL element 1 according to this embodiment, the first electron transport layer is preferably provided in the vicinity of the light emitting layer, and more preferably provided in the vicinity of the light emitting layer. The first electron transport layer prevents triplet excitons generated in the light emitting layer from diffusing into the electron transport band, and increases the density of the triplet excitons by confining the triplet excitons in the light emitting layer. This has a function of efficiently causing a TTF phenomenon (triplet-triplet fusion), which is a phenomenon in which singlet excitons are generated by collisional fusion of triplet excitons.
The first electron transport layer also plays a role of efficiently injecting electrons into the light emitting layer. In the case where the electron injecting property to the light emitting layer is lowered, the density of triplet excitons is reduced by reducing electron-hole recombination in the light emitting layer. When the density of the triplet exciton is reduced, the collision frequency of the triplet exciton decreases, and the TTF phenomenon does not occur efficiently.
Therefore, by providing the first electron transport layer containing the compound represented by the general formula (1) adjacent to the light emitting layer, it is possible to increase the efficiency of the organic EL element.

(Second electron transport layer)
The first electron transport layer of the organic EL device 1 according to this embodiment includes a compound represented by the following general formula (1).

(In the general formula (21),
b is an integer of 1 to 3.
Any one of R ²⁰¹ , R ²⁰² , R ^{206 to} R ²⁰⁹ is a single bond that binds to L ² .
R ²⁰¹ , R ²⁰² , and R ^{206 to} R ²⁰⁹ are the same as R in the general formula (1) except for a single bond bonded to L ² . Adjacent R ²⁰¹ , R ²⁰² , R ^{206 to} R ²⁰⁹ may or may not form a ring by bonding.
L ² is a single bond or a linking group that bonds one of R ²⁰¹ , R ²⁰² , R ^{206 to} R ²⁰⁹ to Ar ^2, and the linking group in L ² is a substituted or unsubstituted carbon number of 1 to 30 Linear, branched or cyclic divalent aliphatic hydrocarbon groups, substituted or unsubstituted ring-forming divalent aromatic hydrocarbon ring groups having 6 to 40 carbon atoms, substituted or unsubstituted ring formation A divalent heterocyclic group having 5 to 40 atoms, a divalent multiple linking group formed by bonding 2 to 3 groups selected from the aromatic hydrocarbon ring group, and 2 selected from the heterocyclic group A divalent multiple linking group formed by bonding from 1 to 3 groups, or a divalent multiple formed by bonding from 2 to 3 groups selected from the aromatic hydrocarbon ring group and the heterocyclic group It is a linking group.
In the multiple linking group, the aromatic hydrocarbon ring group and the heterocyclic group constituting the multiple linking group are the same or different from each other, and the adjacent aromatic hydrocarbon ring group and the heterocyclic group are a ring. May be formed or not formed.
Ar ² is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 40 ring atoms.
Ar ² and L ² may or may not form a ring structure.
However, Ar ² is a L ² is 9-position, and a bound anthracene ring at the 8-position from position 1 hydrogen atom, L ² is an aromatic substituted or unsubstituted having 6 to 40 ring carbon atoms carbide When R ²⁰² is a methyl group or an ethyl group, the atom or group bonded to the carbon atom at the 10-position of the anthracene ring is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a carboxyl group Group, sulfonyl group, mercapto group, substituted or unsubstituted boryl group, substituted or unsubstituted phosphino group, substituted or unsubstituted acyl group, substituted or unsubstituted amino group, substituted or unsubstituted silyl group, substituted or An 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 alkyl group having 2 to 30 carbon atoms; A alkynyl group, a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 40 ring carbon atoms, substituted or Unsubstituted heteroaryloxy group having 5 to 40 ring carbon atoms, substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, substituted or unsubstituted arylthio group having 6 to 40 ring carbon atoms, substituted or unsubstituted A heteroarylthio group having 5 to 40 ring carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryloxycarbonyl group having 6 to 40 ring carbon atoms, substituted or unsubstituted substituted ring-forming hetero aryloxy group having a carbon number of 5 to 40, a substituted or unsubstituted phenyl group F ^100, also substituted Ku is selected from the group consisting of heterocyclic group unsubstituted ring forming condensed aromatic hydrocarbon group F ¹⁰¹ carbon atoms 10 to 40, and substituted or unsubstituted ring atoms ^5-40.
However, when the substituent R ²⁰⁰ is bonded to the substituted or unsubstituted phenyl group F ¹⁰⁰ , the substituent R ²⁰⁰ is not an aromatic hydrocarbon group or a heterocyclic group. When the substituent R ²⁰¹ is bonded to the substituted or unsubstituted condensed aromatic hydrocarbon group F ¹⁰¹ having 10 to 40 ring carbon atoms, the substituent R ²⁰¹ is not an aromatic hydrocarbon group or a heterocyclic group. . )

Ar ² is preferably a group derived from any one of the following general formulas (2a) to (2f), and more preferably a group derived from the following general formula (2a).

  In the general formula (21), b is preferably 1 or 2, and b is more preferably 1.

  The general formula (21) is preferably represented by the following general formula (22).

In (formula (22), ^{L 2} has the same meaning as ^{L 2} in each of the general formula (21).
R ²⁰¹ , R ²⁰² , R ^{206 to} R ²⁰⁹ are each independently synonymous with R ²¹ in the general formula (21). However, any one of R ²⁰¹ , R ²⁰² , and R ^{206 to} R ²⁰⁹ is a single bond that bonds to L ² .
L ²⁰ has the same meaning as L ² in the general formula (21), and Ar ²⁰ has the same meaning as Ar ² in the general formula (21).
p is 8.
R ²¹⁰ each independently represents a hydrogen atom, halogen atom, cyano group, nitro group, hydroxyl group, carboxyl group, sulfonyl group, mercapto group, substituted or unsubstituted boryl group, substituted or unsubstituted phosphino group, substituted or An unsubstituted acyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl 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, Substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted ring-forming carbon An aryloxy group having a number of 6 to 40, a substituted or unsubstituted heteroaryloxy group having a ring carbon number of 5 to 40, and a substitution Or an unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 40 ring carbon atoms, a substituted or unsubstituted heteroarylthio group having 5 to 40 ring carbon atoms, substituted or An unsubstituted alkoxycarbonyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryloxycarbonyl group having 6 to 40 ring carbon atoms, and a substituted or unsubstituted heteroaryloxycarbonyl group having 5 to 40 ring carbon atoms , Selected from the group consisting of
The plurality of R ²¹⁰ are the same or different from each other. Adjacent R ²¹⁰ may or may not form a ring structure.
In addition, L ² and anthracene ring, L ² and R ²¹⁰ , L ²⁰ and anthracene ring, L ²⁰ and R ²¹⁰ , Ar ²⁰ and L ²⁰ may or may not form a ring structure, respectively. )

  The general formula (21) is preferably represented by the following general formula (23).

(In the general formula (23),
At least one of A ²⁰ , A ²² and A ²⁹ is represented by the following formula (201).
^{A 20, A 22} and ^{A 29} other than those represented by the following formula (201) are each ^{independently} a -L 200 ^{-Ar 200.} L ²⁰⁰ has the same meaning as ^{L 2} in Formula ^{(21), Ar 200} has the same meaning as Ar ² in the general formula (21). Note that the bond of L ²⁰⁰ is bonded to the carbon atom of the anthracene ring.
p is 8.
R ²¹⁰ each independently represents a hydrogen atom, halogen atom, cyano group, nitro group, hydroxyl group, carboxyl group, sulfonyl group, mercapto group, substituted or unsubstituted boryl group, substituted or unsubstituted phosphino group, substituted or An unsubstituted acyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl 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, Substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted ring-forming carbon An aryloxy group having a number of 6 to 40, a substituted or unsubstituted heteroaryloxy group having a ring carbon number of 5 to 40, and a substitution Or an unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 40 ring carbon atoms, a substituted or unsubstituted heteroarylthio group having 5 to 40 ring carbon atoms, substituted or An unsubstituted alkoxycarbonyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryloxycarbonyl group having 6 to 40 ring carbon atoms, and a substituted or unsubstituted heteroaryloxycarbonyl group having 5 to 40 ring carbon atoms , Selected from the group consisting of
The plurality of R ²¹⁰ are the same or different from each other. Adjacent R ²¹⁰ may or may not form a ring structure.
A ²⁰ and R ²¹⁰ , A ²⁰ and anthracene ring, A ²² and R ²¹⁰ , A ²² and anthracene ring, A ²⁹ and R ²¹⁰ , A ²⁹ and anthracene ring each form a ring structure, and not There are cases. )

(In the general formula (201), ^{L 2} has the same meaning as ^{L 2} in Formula (21).
R ²⁰¹ , R ²⁰² , R ^{206 to} R ²⁰⁹ are each independently synonymous with R ²¹ in the general formula (21). However, any one of R ²⁰¹ , R ²⁰² , and R ^{206 to} R ²⁰⁹ is a single bond that bonds to L ² . )

  Furthermore, the general formulas (21) and (23) are preferably represented by the following general formula (24).

(In the general formula (24), ^{L 2} has the same meaning as ^{L 2} in Formula (21).
R ²⁰¹ , R ²⁰² , R ^{206 to} R ²⁰⁹ are each independently synonymous with R ²¹ in the general formula (21). However, any one of R ²⁰¹ , R ²⁰² , and R ^{206 to} R ²⁰⁹ is a single bond that bonds to L ² .
L ²⁰ and L ²⁹ are each independently synonymous with L ² in the general formula (21), and Ar ²⁰ and Ar ²⁹ are each independently synonymous with Ar ² in the general formula (21).
Ar ²⁰ and L ²⁰ may or may not form a ring structure. Ar ²⁹ and L ²⁹ may or may not form a ring structure.
p is 8.
R ²¹⁰ each independently represents a hydrogen atom, halogen atom, cyano group, nitro group, hydroxyl group, carboxyl group, sulfonyl group, mercapto group, substituted or unsubstituted boryl group, substituted or unsubstituted phosphino group, substituted or An unsubstituted acyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl 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, Substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted ring-forming carbon An aryloxy group having a number of 6 to 40, a substituted or unsubstituted heteroaryloxy group having a ring carbon number of 5 to 40, and a substitution Or an unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 40 ring carbon atoms, a substituted or unsubstituted heteroarylthio group having 5 to 40 ring carbon atoms, substituted or An unsubstituted alkoxycarbonyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryloxycarbonyl group having 6 to 40 ring carbon atoms, and a substituted or unsubstituted heteroaryloxycarbonyl group having 5 to 40 ring carbon atoms , Selected from the group consisting of
The plurality of R ²¹⁰ are the same or different from each other. Adjacent R ²¹⁰ may or may not form a ring structure.
Also, L ² and anthracene ring, L ² and R ²¹⁰ , L ²⁰ and anthracene ring, L ²⁰ and R ²¹⁰ , L ²⁹ and anthracene ring, and L ²⁹ and R ²¹⁰ each form a ring structure, and not formed There are cases. )

  The general formulas (21) and (22) are preferably represented by any of the following general formulas (25) to (27).

In (Formula (25) ~ (27), ^{L 2} has the same meaning as ^{L 2} in each of the general formula (21).
R ²⁰¹ and R ²⁰² are each independently synonymous with R ²¹ in the formula (21).
L ²⁰ has the same meaning as L ² in the general formula (21), and Ar ²⁰ has the same meaning as Ar ² in the general formula (21). )

In the general formulas (21) to (25) and (27), R ²⁰² is a substituted or unsubstituted linear, branched or cyclic aliphatic hydrocarbon group having 1 to 30 carbon atoms, or a substituted group. Or it is preferably an unsubstituted aromatic hydrocarbon group having 6 to 40 ring carbon atoms, a substituted or unsubstituted linear, branched or cyclic aliphatic hydrocarbon group having 3 to 30 carbon atoms, Or, it is more preferably a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 ring carbon atoms, and particularly preferably a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 ring carbon atoms. .

As the linear, branched or cyclic aliphatic hydrocarbon group having 1 to 30 carbon atoms in R ²⁰² , the aforementioned linear, branched or cyclic alkyl group having 1 to 30 carbon atoms, or the number of carbon atoms Examples thereof include a linear, branched or cyclic alkenyl group having 1 to 30 carbon atoms, and a linear or branched alkynyl group having 1 to 30 carbon atoms. Among these, those having 3 to 30 carbon atoms are more preferable, and an ethyl group, n-propyl group, i-propyl group, cyclopropyl group, i-butyl group, t-butyl group, i-pentyl group, cyclopentyl group, A cyclohexyl group or the like is more preferable.
In addition, the aromatic hydrocarbon group having 6 to 40 ring carbon atoms in R ²⁰² is particularly preferably a phenyl group.

In the general formulas (21) to (27), L ² is a single bond or a linking group, and the linking group is a substituted or unsubstituted divalent aromatic having 6 to 40 ring carbon atoms. A divalent hydrocarbon group, a substituted or unsubstituted divalent heterocyclic group having 5 to 40 ring atoms, and a divalent group formed by bonding 2 to 3 groups selected from the aromatic hydrocarbon ring groups; A multiple linking group, a divalent multiple linking group formed by bonding two to three groups selected from the heterocyclic group, or two to three selected from the aromatic hydrocarbon ring group and the heterocyclic group; It is preferably a divalent multiple linking group formed by bonding a plurality of groups. However, in the multiple linking group, the aromatic hydrocarbon ring group and the heterocyclic group constituting the multiple linking group are the same or different from each other, and the adjacent aromatic hydrocarbon ring group and the heterocyclic group are ring May be formed or not formed.
The L ² is more preferably either a phenylene group or a biphenyldiyl group.

In the general formulas (22) to (26), Ar ²⁰ -L ^20- is preferably represented by the following general formulas (20a) to (20c).

(The bond in the formulas (20a) to (20c) is bonded to the carbon atom constituting the anthracene ring in the general formulas (22) to (26).)

Specific examples of the substituents described in the general formulas (21) to (27) include the general formulas (1), (1A) to (1D), (1-1) to (1-4), (1 -21) (11), (12), (12A), (12B), (12A-1) to (12A-3), (12B-1) to (12B-6), (14), (100) Each group described in the above can be mentioned.
In the general formulas (21) to (27), even when “ring-forming carbon” and “substituted or unsubstituted” are used, the above general formulas (1), (1A) to (1D), (1-1) (1-4), (1-21) (11), (12), (12A), (12B), (12A-1) to (12A-3), (12B-1) to (12B-6) ), (14), and (100).

  Specific examples of the compounds represented by the general formulas (21) to (27) are shown below, but the present invention is not limited to these exemplified compounds.

In the organic EL device 1 according to this embodiment, the second electron transport layer is preferably provided on the cathode side of the first electron transport layer, and the light emitting layer and the second electron transport layer are preferably not adjacent to each other.
The second electron transport layer also preferably contains at least one of an electron donating dopant and an organometallic complex. The content of the electron donating dopant or organometallic complex contained in the electron transport layer is preferably 1% by mass or more and 50% by mass or less.
The electron donating dopant material includes alkali metal, alkaline earth metal, rare earth metal, alkali metal oxide, alkali metal halide, alkaline earth metal oxide, alkaline earth metal halide, rare earth metal. It is preferably one or more selected from the group consisting of oxides and halides of rare earth metals.
The organometallic complex is preferably one or more selected from the group consisting of an organometallic complex containing an alkali metal, an organometallic complex containing an alkaline earth metal, and an organometallic complex containing a rare earth metal. .
Details of the electron donating dopant and the organometallic complex will be described later.

  According to the organic EL device of the present embodiment, the drive voltage can be reduced by containing the compound represented by the general formula (21) in the second electron transport layer. The second electron transport layer contains the compound represented by the general formula (21) and at least one of an electron donating dopant and an organometallic complex, so that the phenanthroline skeleton of the general formula (21) is included. Thus, it becomes easy to supplement the electron donating dopant and the organometallic complex contained in the second electron transport layer, and as a result, the driving voltage is further reduced.

  In the organic EL device of the present embodiment, electrons can be efficiently injected into the light emitting layer by providing the second electron transport layer containing the compound represented by the general formula (21). And the density of a triplet exciton can be raised by providing the 1st electron carrying layer containing the compound represented by the said General formula (1) close to a light emitting layer, Preferably it adjoins. The organic EL device of this embodiment is provided with two layers as an electron transport layer, and these layers have two functions of improving electron injection into the light emitting layer and confining triplet excitons. Thereby, low voltage and high efficiency of the organic EL element can be realized.

(substrate)
The organic EL element of this embodiment is produced on a translucent substrate. The translucent substrate referred to here 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.

(Anode and cathode)
The anode of the organic EL element plays a role of injecting holes into the hole injection layer, the hole transport layer, or the light emitting layer, and it is effective to have 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.

  As the cathode, a material having a small work function is preferable for the purpose of injecting electrons into the electron injection layer, the electron transport layer or the light emitting layer. 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.

(Light emitting layer)
The light emitting layer of the organic EL element provides a field for recombination of electrons and holes, and has a function of connecting this to light emission. The light emitting layer is preferably a molecular deposited film. Here, 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. Can be distinguished from the thin film (molecular accumulation film) formed by the LB method (Langmuir Broadgett method) by the difference in the aggregate structure and higher order structure and the functional difference resulting therefrom.

-Dopant material As a dopant material, it selects from the fluorescent-emitting material which shows the fluorescence type light emission applicable to an organic EL element, or the phosphorescence-emitting material which shows phosphorescence type light emission. When the dopant material is a fluorescent material, the fluorescent material is preferably at least one compound selected from the group consisting of pyrene derivatives, aminoanthracene derivatives, aminochrysene derivatives, and aminopyrene derivatives. Of these, aminopyrene derivatives are more preferable.

-Host material As a host material, the host material which can be applied to an organic EL element is mentioned, For example, an amine derivative, an azine derivative, a condensed polycyclic aromatic derivative, etc. are mentioned.
Examples of amine derivatives include monoamine compounds, diamine compounds, triamine compounds, tetramine compounds, and amine compounds substituted with a carbazole group.
Examples of azine derivatives include monoazine derivatives, diazine derivatives, and triazine derivatives.
The condensed polycyclic aromatic derivative is preferably a condensed polycyclic aryl having no heterocyclic skeleton, and examples thereof include condensed polycyclic aryl such as naphthalene, anthracene, phenanthrene, chrysene, fluoranthene, and triphenylene, or derivatives thereof.
Preferred examples of the combination of the host material and the dopant material include an anthracene derivative as the host material and at least one selected from the group consisting of pyrene derivatives, aminoanthracene derivatives, aminochrysene derivatives, and aminopyrene derivatives as the dopant material. It is a combination of these compounds.

(Hole injection / transport layer)
The hole injection / transport layer is a layer that assists hole injection into the light emitting layer and transports it to the light emitting region, and has a high hole mobility and a low ionization energy.
As a material for forming the hole injection layer and the hole transport layer, a material that transports holes to the light emitting layer with lower electric field strength is preferable. For example, an aromatic amine compound is preferably used. Further, as the material for the hole injection layer, it is preferable to use a porphyrin compound, an aromatic tertiary amine compound or a styrylamine compound. In particular, an aromatic tertiary amine compound such as hexacyanohexaazatriphenylene (HAT) is used. It is preferable to use it.

(Electron injection / transport layer)
The electron injection / transport layer is a layer that assists injection of electrons into the light emitting layer, and has a high electron mobility. The electron injection layer is provided to adjust the energy level, for example, to alleviate a sudden change in the energy level.
In the present embodiment, the electron injection / transport layer includes a first electron transport layer and a second electron transport layer. A 1st electron carrying layer contains the compound represented by the said General formula (1), and a 2nd electron carrying layer contains the compound represented by the said General formula (21). In addition to this, an electron injection layer may be provided, or another electron transport layer may be provided. In the case of having an electron injection layer, the first electron transport layer, the second electron transport layer, and the electron injection layer may be laminated in this order from the anode side. The electron injection layer is a nitrogen-containing ring derivative. It is preferable to contain as a main component. Here, the electron injection layer may be a layer that functions as an electron transport layer. “As a main component” means that the electron injection layer contains 50% by mass or more of a nitrogen-containing ring derivative.
In the organic EL device of the present embodiment, when there are three or more electron transport layers, the first electron transport layer is provided near the light emitting layer, and the second electron transport layer is provided on the cathode side from the first electron transport layer. It is preferable. At this time, the first electron transport layer and the second electron transport layer are preferably close to each other, more preferably adjacent to each other.
Further, the second electron transport layer may contain an alkali metal as described above, and the layer adjacent to the cathode side of the second electron transport layer may contain an alkali metal. In addition to the alkali metal, an electron transporting material described later may be contained.

  As the electron transport material used for the electron injection layer or the electron transport layer, an aromatic heterocyclic compound containing one or more hetero atoms in the molecule is preferably used, and a nitrogen-containing ring derivative is particularly preferable. Further, as the nitrogen-containing ring derivative, 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 is preferable.

(Electron donating dopant and organometallic complex)
The organic EL device of the present embodiment preferably contains at least one of an electron donating dopant and an organometallic complex in a layer adjacent to the cathode side of the second electron transport layer and the second electron transport layer. According to such a configuration, the voltage of the organic EL element can be reduced. Examples of the electron donating dopant include at least one selected from alkali metals, alkali metal compounds, alkaline earth metals, alkaline earth metal compounds, rare earth metals, rare earth metal compounds, and the like.
Examples of the organometallic complex include at least one selected from an organometallic complex containing an alkali metal, an organometallic complex containing an alkaline earth metal, an organometallic complex containing a rare earth metal, and the like.

Examples of the alkali metal include lithium (Li) (work function: 2.93 eV), sodium (Na) (work function: 2.36 eV), potassium (K) (work function: 2.28 eV), rubidium (Rb) (work Function: 2.16 eV), cesium (Cs) (work function: 1.95 eV) and the like, and those having a work function of 2.9 eV or less are particularly preferable. Of these, K, Rb and Cs are preferred, Rb or Cs is more preferred, and Cs is most preferred.
Examples of the alkaline earth metal include calcium (Ca) (work function: 2.9 eV), strontium (Sr) (work function: 2.0 eV to 2.5 eV), barium (Ba) (work function: 2.52 eV). A work function of 2.9 eV or less is particularly preferable.
Examples of the rare earth metal include scandium (Sc), yttrium (Y), cerium (Ce), terbium (Tb), ytterbium (Yb) and the like, and those having a work function of 2.9 eV or less are particularly preferable.
Among the above metals, preferred metals are particularly high in reducing ability, and by adding a relatively small amount to the electron injection region, it is possible to improve the light emission luminance and extend the life of the organic EL element.

Examples of the alkali metal compound include lithium oxide (Li ₂ O), cesium oxide (Cs ₂ O), alkali oxides such as potassium oxide (K ₂ O), lithium fluoride (LiF), sodium fluoride (NaF), fluorine. Examples thereof include alkali halides such as cesium fluoride (CsF) and potassium fluoride (KF), and lithium fluoride (LiF), lithium oxide (Li ₂ O), and sodium fluoride (NaF) are preferable.
Examples of the alkaline earth metal compound include barium oxide (BaO), strontium oxide (SrO), calcium oxide (CaO), and barium strontium oxide (Ba _x Sr _1-x O) (0 <x <1), Examples thereof include barium calcium acid (Ba _x Ca _1-x O) (0 <x <1), and BaO, SrO, and CaO are preferable.
The rare earth metal compound, ytterbium fluoride _(YbF 3), scandium fluoride _(ScF 3), scandium oxide _(ScO 3), yttrium oxide _{(Y 2 O} 3), cerium oxide _{(Ce 2 O} 3), gadolinium fluoride _(GdF 3), such as terbium fluoride (TbF ₃₎ can be _{mentioned, YbF 3, ScF 3, TbF} 3 are preferable.

  The organometallic complex is not particularly limited as long as it contains at least one of alkali metal ions, alkaline earth metal ions, and rare earth metal ions as metal ions. 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 preferable, but not limited thereto.

  Among the electron donating dopant and the organometallic complex, lithium (Li) or lithium fluoride (LiF) is preferable. When at least one of the electron donating dopant and the organometallic complex is contained in the second electron transport layer, lithium (Li) is particularly preferable, and is contained in a layer adjacent to the cathode side of the second electron transport layer. In particular, lithium fluoride (LiF) is preferable.

As an addition form of the electron donating dopant and the organometallic complex, for example, at least one of the electron donating dopant and the organometallic complex is co-deposited with the compound represented by the general formula (1) by a resistance heating vapor deposition method. However, a method of dispersing at least one of an electron donating dopant and an organometallic complex in the electron transport layer is preferable. The dispersion concentration is a film thickness ratio, and is a compound represented by the general formula (1): an electron donating dopant, an organometallic complex = 1000: 1 to 1: 1000, preferably 100: 1 to 1: 1. .
In the case where at least one of the electron donating dopant and the organometallic complex is formed in a layered form, the compound represented by the general formula (21) is formed into a layer and then at least one of the electron donating dopant and the organometallic complex. These are vapor-deposited by a resistance heating vapor deposition method alone, preferably with a layer thickness of 0.1 nm to 15 nm.
When at least one of the electron donating dopant and the organometallic complex is formed in an island shape, the compound represented by the general formula (21) is formed in an island shape, and then at least the electron donating dopant and the organometallic complex are formed. Any one of them is vapor-deposited by a resistance heating vapor deposition method, preferably with an island thickness of 0.05 nm or more and 1 nm or less.
In the organic EL device of the present embodiment, the ratio of the compound represented by the general formula (21) and at least one of the electron donating dopant and the organometallic complex is the main component: electron donating property in the film thickness ratio. Dopant, organometallic complex = 100: 1 to 1: 1 is preferable, and 50: 1 to 4: 1 is more preferable.

(Method for forming each layer of organic EL element)
The formation method of each layer of the organic EL element of this embodiment is not particularly limited. Conventionally known methods such as vacuum deposition and spin coating can be used. The organic layer used in the organic EL device of the present embodiment includes a vacuum deposition method, a molecular beam deposition method (MBE method, MBE; Molecular Beam Epitaxy), a solution dipping method in a solvent, a spin coating method, a casting method, a bar It can be formed by a known method such as a coating method or a roll coating method.

(Thickness of each layer of organic EL element)
The thickness of the light emitting layer is preferably 5 nm to 50 nm, more preferably 7 nm to 50 nm, and most preferably 10 nm to 50 nm. By setting the thickness of the light emitting layer to 5 nm or more, it becomes easy to form the light emitting layer and adjust the chromaticity. By setting the film thickness of the light emitting layer to 50 nm or less, an increase in driving voltage can be suppressed.
The film thickness of each of the other organic layers is not particularly limited, but is usually preferably in the range of several nm to 1 μm. By setting it as such a film thickness range, while preventing defects, such as a pinhole resulting from a film thickness being too thin, the raise of the drive voltage resulting from a film thickness being too thick can be suppressed.

[Electronics]
The organic EL element of the present embodiment can be suitably used by being mounted on an electronic device such as an organic EL panel module, a display device such as a television, a mobile phone, or a personal computer, or a light emitting device for lighting or a vehicle lamp.

<Second embodiment>
Next, a second embodiment will be described.
In the description of the second embodiment, the same components as those in the first embodiment are denoted by the same reference numerals and names, and the description thereof is omitted or simplified. In the second embodiment, the same materials and compounds as those described in the first embodiment can be used.
The organic EL element of the second embodiment is a so-called tandem element that includes a charge generation layer as an intermediate layer and two or more light emitting units. Since the charge supplied from the charge generation layer is injected into the light emitting unit in addition to the charge injected from the pair of electrodes, the emission efficiency (current efficiency) with respect to the injected current is provided by providing the charge generation layer. ) Will improve.

As shown in FIG. 2, the organic EL element 1 </ b> A of the second embodiment includes an anode 3, a first light emitting unit 5 </ b> A, a charge generation layer 20, a second light emitting unit 5 </ b> B, and a cathode 4 on a substrate 2. They are stacked in this order.
The first light emitting unit 5A is configured by laminating a first hole transport layer 71, a first light emitting layer 51, a first electron transport layer 81, and a second electron transport layer 82 in this order from the anode 3 side. .
The second light emitting unit 5B is configured by laminating a second hole transport layer 72, a second light emitting layer 52, and a third electron transport layer 83 in this order from the charge generation layer 20 side.

The charge generation layer 20 is a layer that generates charges when an electric field is applied to the organic EL element 1A, injects electrons into the second electron transport layer 82, and injects holes into the second hole transport layer 72. To do.
As a material of the charge generation layer 20, a known material or a material described in, for example, US 7,358,661 can be used. Specific examples include metal oxides such as In, Sn, Zn, Ti, Zr, Hf, V, Mo, Cu, Ga, Sr, La, and Ru, nitrides, iodides, borides, and the like. In addition, in order for the first light emitting layer 51 to easily receive electrons from the charge generation layer 20, the donor represented by the alkali metal described above may be doped in the vicinity of the charge generation layer interface in the second electron transport layer 82. preferable.

The second hole transport layer 72 and the third electron transport layer 83 are the same as the hole transport layer 7 and the first electron transport layer 81 of the first embodiment.
Since the organic EL element 1A is a so-called tandem element, the driving current can be reduced and the durability can be improved.

[Modification of Embodiment]
In addition, this invention is not limited to the above-mentioned embodiment, The change in the range which can achieve the objective of this invention, improvement, etc. are included in this invention.
In the first embodiment, one light emitting layer is provided. However, the light emitting layer is not limited to one layer, and a plurality of light emitting layers may be stacked. When the organic EL element has a plurality of light emitting layers, each may be independently a fluorescent light emitting layer or a phosphorescent light emitting layer.

It is also preferable that the organic EL device has at least one of an electron donating dopant and an organometallic complex in an interface region between the cathode and the organic layer. According to such a configuration, it is possible to improve the light emission luminance and extend the life of the organic EL element. As the electron donating dopant and the organometallic complex, the same ones as described above can be used.
The addition form of the electron donating dopant and the organometallic complex is preferably formed in a layered or island shape in the interface region. As a forming method, while depositing at least one of an electron donating dopant and an organometallic complex by a resistance heating vapor deposition method, an organic material which is a light-emitting material or an electron injection material for forming an interface region is vapor-deposited at the same time. A method of dispersing at least one of a donor dopant and an organometallic complex reducing dopant is preferable.

  In the present invention, it is also preferable that the light emitting layer contains a charge injection auxiliary material. When a light emitting layer is formed using a host material having a wide energy gap, the difference between the ionization potential (Ip) of the host material and Ip of the hole injection / transport layer, etc. increases, and holes are injected into the light emitting layer. This may make it difficult to increase the driving voltage for obtaining sufficient luminance. In such a case, by adding a hole injection / transport charge injection auxiliary material to the light emitting layer, hole injection into the light emitting layer can be facilitated and the driving voltage can be lowered.

As the charge injection auxiliary material, for example, a general hole injection / transport material or the like can be used.
Specific examples include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, fluorenone derivatives, hydrazone derivatives, stilbenes. Derivatives, silazane derivatives, polysilane-based, aniline-based copolymers, conductive polymer oligomers (particularly thiophene oligomers), and the like can be given.

  Examples of the hole-injecting material include those described above, and porphyrin compounds, aromatic tertiary amine compounds and styrylamine compounds, particularly aromatic tertiary amine compounds are preferred.

In addition, for example, 4,4′-bis (N- (1-naphthyl) -N-phenylamino) biphenyl (hereinafter abbreviated as NPD) having two condensed aromatic rings in the molecule, or triphenylamine 4,4 ′, 4 ″ -tris (N- (3-methylphenyl) -N-phenylamino) triphenylamine (hereinafter abbreviated as MTDATA) and the like in which three units are connected in a starburst type. it can.
A hexaazatriphenylene derivative or the like can also be suitably used as the hole injecting material.
In addition, inorganic compounds such as p-type Si and p-type SiC can also be used as the hole injection material.

  EXAMPLES Next, although an Example and a comparative example are given and this invention is demonstrated in more detail, this invention is not restrict | limited at all to the description content of these Examples.

[Synthesis of compounds]
-Synthesis | combination of ET-11 ET-11 was synthesize | combined like the synthesis | combining method (synthesis example 14) of the compound A98 as described in international publication 2003/080760.

-Synthesis | combination of ET-13 The synthetic scheme of ET-13 is shown next.

(1-1) Synthesis of Compound 13-3 Compound 13-1 (37 g, 191 mmol), Compound 13-2 (50 g, 191 mmol), sodium methoxide (8.4 g, 156 mmol), and ethanol (200 mL) were mixed. And stirred at room temperature for 12 hours. The precipitated solid was collected by filtration, suspended and washed with ethanol, and then dried under reduced pressure to obtain Compound 13-3 (82 g, yield 98%) as a yellow solid.

(1-2) Synthesis of Compound 13-5 Compound 13-4 (82 g, 186 mmol), benzamidine hydrochloride (Compound 4) (26 g, 166 mmol), and sodium hydroxide (12 g, 299 mmol) were added to ethanol (450 mL). And heated to reflux for 9 hours. After completion of the reaction, the precipitate was collected by filtration and purified by silica gel column chromatography (developing solvent: toluene). Further, recrystallization with toluene gave Compound 13-5 (40 g, yield 40%) as a white solid.

(1-3) Synthesis of Compound ET-13 Compound 13-5 (6.0 g, 11 mmol) and compound 13-6 (4.9 g, 24 mmol) were added to toluene (200 mL) and 1,2-dimethoxyethane (200 mL). After dissolution, tetrakis (triphenylphosphine) palladium (0) (0.75 g, 0.65 mmol) and 2M aqueous sodium carbonate solution (26 mL) were added, and the mixture was heated to reflux for 15 hours. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with toluene. The obtained organic layer was washed successively with water and saturated brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. Toluene was added to the residue, dissolved by heating under reflux, allowed to cool, and the precipitated crystals were collected by filtration, washed with toluene, and dried under reduced pressure to give Compound ET-13 (4.2 g, yield 53%) as a white color. Obtained as a solid. The powder was identified as Compound ET-13 by FD-MS (field desorption mass spectrum) analysis.

-Synthesis | combination of ET-23 ET-23 was synthesize | combined like the synthesis | combining method (Synthesis example 7) of the compound 7-2 as described in international publication 2004/080975.
-Synthesis | combination of ET-26 ET-26 was synthesize | combined using the synthesis method (synthesis example 4) of the compound 1-41 of the international publication 2005/097756.

[Manufacture of organic EL elements]
Example 1
A 25 mm × 75 mm × 0.7 mm thick glass substrate with ITO transparent electrode (anode) (manufactured by Geomatic) 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 the cleaning was mounted on a substrate holder of a vacuum vapor deposition apparatus. First, the following compound HAT was vapor deposited so as to cover the transparent electrode line to form a HAT film having a film thickness of 5 nm. The HAT film functions as a hole injection layer. Subsequently, the following compound HT-1 was deposited to form a 95 nm-thick HT-1 film on the HAT film. The HT-1 film functions as a hole transport layer.
The following compound BH-1 (host material) and the following compound BD-1 (dopant material) are vapor-deposited on the HT-1 film at a film thickness ratio such that the compound BD-1 is 5% by mass, and the organic layer has a film thickness of 25 nm. Was deposited. This organic layer functions as a light emitting layer.
The following compound ET-11 was vapor-deposited on the light emitting layer to form a 20 nm thick ET-11 film. The ET-11 film functions as a first electron transport layer. On the ET-11 film, the following compound ET-22 and lithium (Li) were vapor-deposited at a film thickness ratio such that Li was 4% by mass to form a 5 nm thick ET-21 film. The ET-22 film functions as a second electron transport layer. On this electron transport layer, metal Al was deposited to a thickness of 80 nm to form a metal cathode, thereby producing an organic EL device.

-Examples 2-18 and Comparative Examples 1-4
The organic EL elements of Examples 2 to 18 and Comparative Examples 1 to 4 except that at least one of the materials for the first electron transport layer and the second electron transport layer in Example 1 was changed to the compounds shown in Table 1. Was prepared in the same manner as in Example 1.

  The compound used for manufacture of an organic EL element is shown below.

[Evaluation of organic EL elements]
About the produced organic EL element, voltage was applied so that a current density might be 10 mA / cm < ² >, and the voltage (V) at that time was measured. Moreover, the external quantum efficiency EQE was calculated | required as follows.
The voltage (V) and external quantum efficiency EQE are shown in Table 2 as the ratio of the values of Examples 1-18 and Comparative Examples 1-3 to the values of Comparative Example 4.

・ External quantum efficiency EQE
The spectral radiance spectrum when a voltage is applied to the device so that the current density is 10 mA / cm ² is measured with the above-mentioned spectral radiance meter, and it is assumed that Lambertian radiation is performed from the obtained spectral radiance spectrum. Efficiency EQE (unit:%) was calculated.

DESCRIPTION OF SYMBOLS 1,1A ... Organic EL element 2 ... Substrate 3 ... Anode 4 ... Cathode 5 ... Light emitting layer 6 ... Hole injection layer 7 ... Hole transport layer 81 ... First electron transport layer 82 ... Second electron transport layer 9 ... Electron injection Layer 10 ... Organic layer

Claims (28)

The anode,
A cathode provided opposite to the anode;
An organic layer provided between the anode and the cathode,
The organic layer includes a light emitting layer, a first electron transport layer provided between the light emitting layer and the cathode,
A second electron transport layer provided between the first electron transport layer and the cathode;
The first electron transport layer includes a compound represented by the following general formula (1),
Said 2nd electron carrying layer contains the compound represented by following General formula (21), The organic electroluminescent element characterized by the above-mentioned.
[In the general formula (1),
X ¹ to X ⁶ are each independently a nitrogen atom, CR, CA, CR ¹¹ , or CR ¹² . However, at least one of X ¹ to X ⁶ is a nitrogen atom.
R is independently hydrogen atom, halogen atom, cyano group, nitro group, hydroxyl group, carboxyl group, sulfonyl group, mercapto group, substituted or unsubstituted boryl group, substituted or unsubstituted phosphino group, substituted or unsubstituted Substituted acyl group, substituted or unsubstituted amino group, substituted or unsubstituted silyl group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted Or an unsubstituted alkynyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted ring forming carbon number 6 to 40 aryloxy groups, substituted or unsubstituted heteroaryloxy groups having 5 to 40 ring carbon atoms, substituted or unsubstituted Substituted alkylthio group having 1 to 30 carbon atoms, substituted or unsubstituted arylthio group having 6 to 40 ring carbon atoms, substituted or unsubstituted heteroarylthio group having 5 to 40 ring carbon atoms, substituted or unsubstituted An alkoxycarbonyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryloxycarbonyl group having 6 to 40 ring carbon atoms, a substituted or unsubstituted heteroaryloxycarbonyl group having 5 to 40 ring carbon atoms, substituted or unsubstituted It is selected from the group consisting of a substituted aromatic hydrocarbon group having 6 to 40 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 40 ring atoms.
R ¹¹ and R ¹² are each a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 40 ring atoms, or the following general formula It is group represented by (11).
A is represented by the following general formula (11).
(In the general formula (11),
a is an integer of 1 to 5.
L ¹ is a single bond or a linking group, and the linking group in L ¹ is a substituted or unsubstituted C 1-30 linear, branched or cyclic polyvalent aliphatic hydrocarbon group, substituted or Unsubstituted polyvalent amino group, substituted or unsubstituted polyvalent aromatic hydrocarbon ring group having 6 to 40 ring carbon atoms, substituted or unsubstituted polyvalent heterocyclic ring having 5 to 40 ring atoms A divalent multiple linking group formed by bonding two to three groups selected from the aromatic hydrocarbon ring group, and two to three groups selected from the heterocyclic group bonded together It is a divalent multiple linking group or a divalent multiple linking group formed by bonding two to three groups selected from the aromatic hydrocarbon ring group and the heterocyclic group.
In the multiple linking group, the aromatic hydrocarbon ring group and the heterocyclic group constituting the multiple linking group may be the same or different from each other, and may be bonded to each other to form a ring. Good.
Ar ¹ is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 40 ring atoms. When a is 2 or more and 5 or less, Ar ¹ is the same or different from each other.
Ar ¹ and L ¹ may or may not form a ring structure. ]]
(In the general formula (21),
b is an integer of 1 to 3.
Any one of R ²⁰¹ , R ²⁰² , R ^{206 to} R ²⁰⁹ is a single bond that binds to L ² .
R ²⁰¹ , R ²⁰² , and R ^{206 to} R ²⁰⁹ are the same as R in the general formula (1) except for a single bond bonded to L ² . Adjacent R ²⁰¹ , R ²⁰² , R ^{206 to} R ²⁰⁹ may or may not form a ring by bonding.
L ² is a single bond or a linking group that bonds one of R ²⁰¹ , R ²⁰² , R ^{206 to} R ²⁰⁹ to Ar ^2, and the linking group in L ² is a substituted or unsubstituted carbon number of 1 to 30 Linear, branched or cyclic divalent aliphatic hydrocarbon groups, substituted or unsubstituted ring-forming divalent aromatic hydrocarbon ring groups having 6 to 40 carbon atoms, substituted or unsubstituted ring formation A divalent heterocyclic group having 5 to 40 atoms, a divalent multiple linking group formed by bonding 2 to 3 groups selected from the aromatic hydrocarbon ring group, and 2 selected from the heterocyclic group A divalent multiple linking group formed by bonding from 1 to 3 groups, or a divalent multiple formed by bonding from 2 to 3 groups selected from the aromatic hydrocarbon ring group and the heterocyclic group It is a linking group.
In the multiple linking group, the aromatic hydrocarbon ring group and the heterocyclic group constituting the multiple linking group are the same or different from each other, and the adjacent aromatic hydrocarbon ring group and the heterocyclic group are a ring. May be formed or not formed.
Ar ² is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 40 ring atoms.
Ar ² and L ² may or may not form a ring structure.
However, Ar ² is a L ² is 9-position, and a bound anthracene ring at the 8-position from position 1 hydrogen atom, L ² is an aromatic substituted or unsubstituted having 6 to 40 ring carbon atoms carbide When R ²⁰² is a methyl group or an ethyl group, the atom or group bonded to the carbon atom at the 10-position of the anthracene ring is a hydrogen atom, a halogen atom, a cyano group, a nitro group, a hydroxyl group, a carboxyl group Group, sulfonyl group, mercapto group, substituted or unsubstituted boryl group, substituted or unsubstituted phosphino group, substituted or unsubstituted acyl group, substituted or unsubstituted amino group, substituted or unsubstituted silyl group, substituted or An 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 alkyl group having 2 to 30 carbon atoms; A alkynyl group, a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 40 ring carbon atoms, substituted or Unsubstituted heteroaryloxy group having 5 to 40 ring carbon atoms, substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, substituted or unsubstituted arylthio group having 6 to 40 ring carbon atoms, substituted or unsubstituted A heteroarylthio group having 5 to 40 ring carbon atoms, a substituted or unsubstituted alkoxycarbonyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryloxycarbonyl group having 6 to 40 ring carbon atoms, substituted or unsubstituted substituted ring-forming hetero aryloxy group having a carbon number of 5 to 40, a substituted or unsubstituted phenyl group F ^100, also substituted Ku is selected from the group consisting of heterocyclic group unsubstituted ring forming condensed aromatic hydrocarbon group F ¹⁰¹ carbon atoms 10 to 40, and substituted or unsubstituted ring atoms ^5-40.
However, when the substituent R ²⁰⁰ is bonded to the substituted or unsubstituted phenyl group F ¹⁰⁰ , the substituent R ²⁰⁰ is not an aromatic hydrocarbon group or a heterocyclic group. When the substituent R ²⁰¹ is bonded to the substituted or unsubstituted condensed aromatic hydrocarbon group F ¹⁰¹ having 10 to 40 ring carbon atoms, the substituent R ²⁰¹ is not an aromatic hydrocarbon group or a heterocyclic group. . ) 2. The organic electroluminescence element according to claim 1, wherein Ar ² is a group derived from any one of the following general formulas (2a) to (2f).
2. The organic electroluminescence device according to claim 1, wherein the general formula (21) is represented by the following general formula (22).
(In the general formula (22), ^{L 2} has the same meaning as ^{L 2} in formula each (21).
R ²⁰¹ , R ²⁰² , R ^{206 to} R ²⁰⁹ are each independently synonymous with R ²¹ in the general formula (21). However, any one of R ²⁰¹ , R ²⁰² , and R ^{206 to} R ²⁰⁹ is a single bond that bonds to L ² .
L ²⁰ has the same meaning as L ² in the general formula (21), and Ar ²⁰ has the same meaning as Ar ² in the general formula (21).
p is 8.
R ²¹⁰ each independently represents a hydrogen atom, halogen atom, cyano group, nitro group, hydroxyl group, carboxyl group, sulfonyl group, mercapto group, substituted or unsubstituted boryl group, substituted or unsubstituted phosphino group, substituted or An unsubstituted acyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl 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, Substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted ring-forming carbon An aryloxy group having a number of 6 to 40, a substituted or unsubstituted heteroaryloxy group having a ring carbon number of 5 to 40, and a substitution Or an unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 40 ring carbon atoms, a substituted or unsubstituted heteroarylthio group having 5 to 40 ring carbon atoms, substituted or An unsubstituted alkoxycarbonyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryloxycarbonyl group having 6 to 40 ring carbon atoms, and a substituted or unsubstituted heteroaryloxycarbonyl group having 5 to 40 ring carbon atoms , Selected from the group consisting of
The plurality of R ²¹⁰ are the same or different from each other. Adjacent R ²¹⁰ may or may not form a ring structure.
In addition, L ² and anthracene ring, L ² and R ²¹⁰ , L ²⁰ and anthracene ring, L ²⁰ and R ²¹⁰ , Ar ²⁰ and L ²⁰ may or may not form a ring structure, respectively. ) 2. The organic electroluminescence device according to claim 1, wherein the general formula (21) is represented by the following formula (23).
(In the general formula (23), at least one of A ²⁰ , A ²² and A ²⁹ is represented by the following formula (201).
^{A 20, A 22} and ^{A 29} other than those represented by the following formula (201) are each ^{independently} a -L 200 ^{-Ar 200.} L ²⁰⁰ has the same meaning as ^{L 2} in Formula ^{(21), Ar 200} has the same meaning as Ar ² in the general formula (21). Note that the bond of L ²⁰⁰ is bonded to the carbon atom of the anthracene ring.
p is 8.
R ²¹⁰ each independently represents a hydrogen atom, halogen atom, cyano group, nitro group, hydroxyl group, carboxyl group, sulfonyl group, mercapto group, substituted or unsubstituted boryl group, substituted or unsubstituted phosphino group, substituted or An unsubstituted acyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl 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, Substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted ring-forming carbon An aryloxy group having a number of 6 to 40, a substituted or unsubstituted heteroaryloxy group having a ring carbon number of 5 to 40, and a substitution Or an unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 40 ring carbon atoms, a substituted or unsubstituted heteroarylthio group having 5 to 40 ring carbon atoms, substituted or An unsubstituted alkoxycarbonyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryloxycarbonyl group having 6 to 40 ring carbon atoms, and a substituted or unsubstituted heteroaryloxycarbonyl group having 5 to 40 ring carbon atoms , Selected from the group consisting of
The plurality of R ²¹⁰ are the same or different from each other. Adjacent R ²¹⁰ may or may not form a ring structure.
A ²⁰ and R ²¹⁰ , A ²⁰ and anthracene ring, A ²² and R ²¹⁰ , A ²² and anthracene ring, A ²⁹ and R ²¹⁰ , A ²⁹ and anthracene ring each form a ring structure, and not There are cases. )
(In the general formula (201), ^{L 2} has the same meaning as ^{L 2} in Formula (21).
R ²⁰¹ , R ²⁰² , R ^{206 to} R ²⁰⁹ are each independently synonymous with R ²¹ in the general formula (21). However, any one of R ²⁰¹ , R ²⁰² , and R ^{206 to} R ²⁰⁹ is a single bond that bonds to L ² . ) 2. The organic electroluminescence device according to claim 1, wherein the general formula (21) is represented by the following general formula (24).
(In the general formula (24), ^{L 2} has the same meaning as ^{L 2} in Formula (21).
R ²⁰¹ , R ²⁰² , R ^{206 to} R ²⁰⁹ are each independently synonymous with R ²¹ in the general formula (21). However, any one of R ²⁰¹ , R ²⁰² , and R ^{206 to} R ²⁰⁹ is a single bond that bonds to L ² .
L ²⁰ and L ²⁹ are each independently synonymous with L ² in the general formula (21), and Ar ²⁰ and Ar ²⁹ are each independently synonymous with Ar ² in the general formula (21).
Ar ²⁰ and L ²⁰ may or may not form a ring structure. Ar ²⁹ and L ²⁹ may or may not form a ring structure.
p is 8.
R ²¹⁰ each independently represents a hydrogen atom, halogen atom, cyano group, nitro group, hydroxyl group, carboxyl group, sulfonyl group, mercapto group, substituted or unsubstituted boryl group, substituted or unsubstituted phosphino group, substituted or An unsubstituted acyl group, a substituted or unsubstituted amino group, a substituted or unsubstituted silyl 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, Substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted ring-forming carbon An aryloxy group having a number of 6 to 40, a substituted or unsubstituted heteroaryloxy group having a ring carbon number of 5 to 40, and a substitution Or an unsubstituted alkylthio group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 40 ring carbon atoms, a substituted or unsubstituted heteroarylthio group having 5 to 40 ring carbon atoms, substituted or An unsubstituted alkoxycarbonyl group having 2 to 30 carbon atoms, a substituted or unsubstituted aryloxycarbonyl group having 6 to 40 ring carbon atoms, and a substituted or unsubstituted heteroaryloxycarbonyl group having 5 to 40 ring carbon atoms , Selected from the group consisting of
The plurality of R ²¹⁰ are the same or different from each other. Adjacent R ²¹⁰ may or may not form a ring structure.
Also, L ² and anthracene ring, L ² and R ²¹⁰ , L ²⁰ and anthracene ring, L ²⁰ and R ²¹⁰ , L ²⁹ and anthracene ring, and L ²⁹ and R ²¹⁰ each form a ring structure, and not formed There are cases. ) The organic electroluminescent element of Claim 1 WHEREIN: The said general formula (21) is represented by either of the following general formula (25)-(27), The organic electroluminescent element characterized by the above-mentioned.
In (Formula (25) ~ (27), ^{L 2} has the same meaning as ^{L 2} in each of the general formula (21).
R ²⁰¹ and R ²⁰² are each independently synonymous with R ²¹ in the formula (21).
L ²⁰ has the same meaning as L ² in the general formula (21), and Ar ²⁰ has the same meaning as Ar ² in the general formula (21). ) The organic electroluminescent element according to any one of claims 1 to 6, wherein the R ²⁰² is a substituted or unsubstituted linear, branched or cyclic aliphatic group having 1 to 30 carbon atoms. An organic electroluminescence device, which is a hydrocarbon group or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 ring carbon atoms. The organic electroluminescent element according to any one of claims 1 to 7, wherein the R ²⁰² is a substituted or unsubstituted C3-C30 linear, branched or cyclic aliphatic. An organic electroluminescence device, which is a hydrocarbon group or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 ring carbon atoms. The organic electroluminescence device according to any one of claims 1 to 8, wherein R ²⁰² is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 ring carbon atoms. An organic electroluminescence element. 10. The organic electroluminescence device according to claim 1, wherein the L ² is a single bond or a linking group, and the linking group has a substituted or unsubstituted ring carbon number of 6 to 6. 2 to 3 groups selected from 40 divalent aromatic hydrocarbon ring groups, substituted or unsubstituted divalent heterocyclic groups having 5 to 40 ring atoms, and the aromatic hydrocarbon ring group A divalent multiple linking group formed by bonding, a divalent multiple linking group formed by bonding two to three groups selected from the heterocyclic group, or the aromatic hydrocarbon ring group and the heterocyclic group It is a divalent multiple linking group formed by bonding 2 to 3 groups selected from
In the multiple linking group, the aromatic hydrocarbon ring group and the heterocyclic group constituting the multiple linking group are the same or different from each other, and the adjacent aromatic hydrocarbon ring group and the heterocyclic group form a ring. An organic electroluminescence element characterized by having a case and not forming. The organic electroluminescence device according to any one of claims 1 to 10, wherein the L ² is a single bond or a linking group, and the linking group has a substituted or unsubstituted ring carbon number of 6 to 6. 40. An organic electroluminescence device comprising 40 divalent aromatic hydrocarbon ring groups. The organic electroluminescence device according to any one of claims 1 to 11, wherein the L ² is either a phenylene group or a biphenyldiyl group. The organic electroluminescent element according to any one of claims 5 to 12, wherein Ar ²⁰ -L ²⁰ -is represented by any one of the following formulas (20a) to (20c): Organic electroluminescence device.
(The bond in the formulas (20a) to (20c) is bonded to the carbon atom constituting the anthracene ring in the general formulas (22) to (26).) The organic electroluminescent element according to any one of claims 1 to 13, wherein Ar ¹ in the general formula (11) is represented by the following general formula (12). element.
(In the general formula (12),
X ¹¹ to X ¹⁸ each independently represent a nitrogen atom or CR ¹³ .
Z ¹ is an oxygen atom, a sulfur atom, NR ¹⁴ , CR ¹⁵ R ¹⁶ , or SiR ¹⁷ R ¹⁸ .
R ¹³ to R ¹⁸ have the same meaning as R in the general formula (1).
However, any one of R ¹³ to R ¹⁸ is a single bond that bonds to L ¹ of the general formula (11).
If the formula (12) has a plurality of ^{R 13, R 13} are the same or different from each other.
Further, R ^{13 of} adjacent CR ¹³ may be bonded to each other to form a saturated or unsaturated ring. When Z ¹ is NR ¹⁴ , CR ¹⁵ R ¹⁶ , or SiR ¹⁷ R ¹⁸ , and at least one of X ¹¹ and X ¹⁸ is CR ¹³ , any one of R ¹⁴ to R ¹⁸ is one of R ¹³ may be bonded to each other to form a ring. Alternatively, Z ¹ may be directly bonded to one R ¹³ to form a ring.
In addition, R ¹³ to R ¹⁸ other than a single bond bonded to L ¹ may be further bonded to L ¹ of the general formula (11) to form a saturated or unsaturated ring. Good. ) 15. The organic electroluminescence device according to claim 14, wherein X ¹³ or X ^{16 in} the general formula (12) is CR ¹³ and R ¹³ is a single bond bonded to L ^1. Luminescence element. 15. The organic electroluminescence device according to claim 14, wherein X ¹¹ or X ^{18 in} the general formula (12) is CR ¹³ and R ¹³ is a single bond bonded to L ^1. Luminescence element. The organic electroluminescence device according to any one of claims 14 to 16, wherein Z ^{1 in the} general formula (12) is NR ¹⁴ , and X ¹¹ to X ¹⁸ are CR ^13. An organic electroluminescence element. The organic electroluminescent element according to any one of claims 1 to 13, wherein Ar ^{1 in the} general formula (11) is a substituted or unsubstituted condensed aromatic hydrocarbon having 8 to 20 ring carbon atoms. An organic electroluminescence element characterized by being a group. The organic electroluminescent element according to any one of claims 1 to 13, wherein Ar ^{1 in the} general formula (11) is a group represented by the following general formula (14). Organic electroluminescence device.
(In the general formula (14),
t represents an integer of 1 to 3.
n represents an integer of 1 or more and 4 or less.
R ¹¹¹ has the same meaning as R in the general formula (1), and the plurality of R ¹¹¹ are the same as or different from each other.
L ¹¹ and L ¹² have the same meaning as L ^{1 in the} general formula (11).
Ar ¹² is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 40 ring atoms.
L ¹¹ is single-bonded to L ¹ in the general formula (11). A plurality of R ¹¹¹ are each bonded to any carbon atom of the carbazolyl group, and the two carbazolyl groups are bonded to each other at any position from the 1st position to the 4th position. ) In the organic electroluminescent element according to any one of claims 1 to 19, a in the general formula (11) is 1 or 2, L ¹ is a linking group,
The linking group in L ¹ is a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 40 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 40 ring atoms. An organic electroluminescence device characterized in that there is. The organic electroluminescent element according to any one of claims 1 to 20, wherein R ¹¹ or R ¹² of the general formula (1) is selected from the group consisting of the following formulas (1a) to (1p). An organic electroluminescence device characterized by being a group.
The organic electroluminescent element according to claim 21, wherein X ¹ and X ^{3 in} the general formula (1) are nitrogen atoms, X ⁴ is CR ¹² , and R ¹² is the formula (1a) to ( An organic electroluminescence device, which is a group selected from the group consisting of 1p). The organic electroluminescence device according to any one of claims 1 to 22, wherein the general formula (1) is represented by the following general formula (1-1). The organic electroluminescent element of description.
In (Formula ^{(1-1), R 11} is, .L ¹ and ^{L 121} are the same meaning as ^{R 11} in the formula (1) has the same meaning as ^{L 1} in the general formula (11) .a is In the general formula (11), Ar ¹²¹ has the same meaning as Ar ¹ in the general formula (11), and Z ¹ and X ^{11 to} X ¹⁸ are the same as those in the general formula (12), respectively. L ¹ is bonded to Z ¹ and any ^one of X ^{11 to} X ¹⁸ . The organic electroluminescent element according to any one of claims 1 to 23, wherein the general formula (1) is represented by the following general formula (1-4). .
(In the general formula (1-4), R ¹¹ , L ¹²¹ , Ar ¹²¹ , and Cz have the same meanings as those in the general formula (1-2). R ¹⁰¹ and c each represent the general formula (1 -21)), the carbazolyl group and the pyrimidine ring are bonded to any carbon atom of the benzene ring, and R ¹⁰¹ is bonded to any carbon atom of the carbazolyl group.)   The organic electroluminescent element according to any one of claims 1 to 24, wherein the first electron transport layer and the light emitting layer are adjacent to each other.   The organic electroluminescent element according to any one of claims 1 to 25, wherein the light emitting layer includes an anthracene derivative as a host material.   The organic electroluminescence device according to any one of claims 1 to 26, wherein the light-emitting layer includes, as a dopant material, a pyrene derivative, an anthracene derivative, an aminochrysene derivative, an aminopyrene derivative, a fluoranthene derivative, and a boron complex. An organic electroluminescence device comprising at least one compound selected from the group consisting of:   An electronic apparatus comprising the organic electroluminescence element according to any one of claims 1 to 27.