WO2015115529A1

WO2015115529A1 - Compound, material for organic electroluminescent elements, organic electroluminescent element and electronic device

Info

Publication number: WO2015115529A1
Application number: PCT/JP2015/052480
Authority: WO
Inventors: 裕勝伊藤; 河村　昌宏; 由美子水木; 匡羽毛田; 友治羽山
Original assignee: 出光興産株式会社
Priority date: 2014-01-31
Filing date: 2015-01-29
Publication date: 2015-08-06
Also published as: JPWO2015115529A1

Abstract

This organic electroluminescent element, which uses a compound of a specific structure having a fluoranthene skeleton, can be driven at a low voltage and is able to have at least a higher luminous efficiency or a longer service life.

Description

COMPOUND, MATERIAL FOR ORGANIC ELECTROLUMINESCENT ELEMENT, ORGANIC ELECTROLUMINESCENT ELEMENT, AND ELECTRONIC DEVICE

The present invention relates to a compound, a material for an organic electroluminescence device comprising the compound, an organic electroluminescence device using the compound, and an electronic device equipped with the organic electroluminescence device.

In general, an organic electroluminescence element (hereinafter also referred to as “organic EL element”) is composed of an anode, a cathode, and an organic thin film layer composed of one or more layers sandwiched between the anode and the cathode. When a voltage is applied between both electrodes, electrons from the cathode side and holes from the anode side are injected into the light emitting region, and the injected electrons and holes recombine in the light emitting region to generate an excited state, which is excited. Light is emitted when the state returns to the ground state.
In addition, organic EL elements can obtain various emission colors by using various light emitting materials for the light emitting layer, and therefore, researches for practical application to displays and the like are active. In particular, research on light emitting materials of the three primary colors of red, green, and blue is the most active, and intensive research has been conducted with the aim of improving characteristics.
As characteristics of such an organic EL element, further improvement in light emission efficiency and reduction in driving voltage are required.

JP 2012-241016 A JP 2012-241017 A JP 2013-023572 A JP 2004-095221 A

Accordingly, an object of the present invention is to provide an organic electroluminescence element that can be driven at a low voltage and can at least increase the efficiency of light emission or extend the life, and an electronic device equipped with the organic electroluminescence element. And providing a compound for realizing them.

As a result of intensive studies, the present inventors have found that a compound having a specific structure having a fluoranthene skeleton can solve the above problems. The present invention has been completed based on such findings.

According to one aspect of the present invention, the following [1] to [4] are provided.
[1] A compound represented by the following general formula (1).

[In the formula (1), X ¹ to X ¹⁰ each represent C (R ^A1 ) to C (R ^A10 ) or a nitrogen atom.
However, at least two selected from R ^A1 to R ^A10 are bonded to each other to form a saturated or unsaturated ring.
R ^A1 to R ^A10 each independently represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted group Aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted arylthio group, substituted or unsubstituted silyl group, substituted or unsubstituted An amino group or a group represented by the following general formula (2).
However, at least one of R ^A1 to R ^A10 (including a group bonded to a carbon atom constituting the ring at a position where each ring is bonded to each other) is represented by the following general formula (2) It is group represented by these.

(In Formula (2), Z shows an oxygen atom, a sulfur atom, or a selenium atom.
L ¹ is a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms, or a bond of 2 to 4 of these groups Is a divalent group.
Ar ¹ and Ar ² are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, and Ar ¹ And Ar ² may be bonded to each other to form a ring. )]
[2] A material for an organic electroluminescence device comprising the compound according to [1].
[3] It has an organic thin film layer composed of one or more layers including at least a light emitting layer between an anode and a cathode facing each other, and at least one of the organic thin film layers contains the compound according to the above [1] An organic electroluminescence device.
[4] An electronic device equipped with the organic electroluminescence element according to [3].

According to the present invention, it is possible to provide an organic electroluminescence element that can be driven at a low voltage and can at least increase the efficiency of light emission or extend the lifetime, and an electronic device equipped with the organic electroluminescence element. Furthermore, the compound which can implement | achieve them can be provided.

It is a figure which shows an example of schematic structure of the organic electroluminescent element which concerns on embodiment of this invention.

In the present specification, the “carbon number XX to YY” in the expression “substituted or unsubstituted ZZ group having XX to YY” represents the number of carbon atoms in the case where the ZZ group is unsubstituted. The carbon number of the substituent in the case where it is present is not included. Here, “YY” is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.
Further, in this specification, “atom number XX to YY” in the expression “ZZ group of substituted or unsubstituted atoms XX to YY” represents the number of atoms when the ZZ group is unsubstituted. In the case of substitution, the number of substituent atoms is not included. Here, “YY” is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.

In this specification, the number of ring-forming carbon atoms constitutes the ring itself of a compound having a structure in which atoms are bonded cyclically (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, or a heterocyclic compound). Represents the number of carbon atoms in the atom. 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” described below is the same unless otherwise specified. For example, the benzene ring has 6 ring carbon atoms, the naphthalene ring has 10 ring carbon atoms, the pyridinyl group has 5 ring carbon atoms, and the furanyl group has 4 ring carbon atoms. Further, when an alkyl group is substituted as a substituent on the benzene ring or naphthalene ring, the carbon number of the alkyl group is not included in the number of ring-forming carbons. In addition, for example, when a fluorene ring is bonded to the fluorene ring as a substituent (including a spirofluorene ring), the carbon number of the fluorene ring as a substituent is not included in the number of ring-forming carbons.
In this specification, the number of ring-forming atoms refers to a compound (for example, a monocyclic compound, a condensed ring compound, a bridged compound, or a carbocyclic compound) having a structure in which atoms are bonded in a cyclic manner (for example, a single ring, a condensed ring, or a ring assembly) , A heterocyclic compound) represents the number of atoms constituting the ring itself. An atom that does not constitute a ring (for example, a hydrogen atom that terminates a bond of an atom that constitutes a ring) or an atom contained in a substituent when the ring is substituted by a substituent is not included in the number of ring-forming atoms. The “number of ring-forming atoms” described below is the same unless otherwise specified. For example, the number of ring-forming atoms in the pyridine ring is 6, the number of ring-forming atoms in the quinazoline ring is 10, and the number of ring-forming atoms in the furan ring is 5. A hydrogen atom bonded to a carbon atom of a pyridine ring or a quinazoline ring or an atom constituting a substituent is not included in the number of ring-forming atoms. Further, when, for example, a fluorene ring is bonded to the fluorene ring as a substituent (including a spirofluorene ring), the number of atoms of the fluorene ring as a substituent is not included in the number of ring-forming atoms.

In the present specification, “hydrogen atom” includes isotopes having different numbers of neutrons, that is, light hydrogen (protium), deuterium (deuterium), and tritium (tritium).
In the present specification, the “heteroaryl group” and the “heteroarylene group” are groups containing at least one heteroatom as a ring-forming atom, and the heteroatom includes a nitrogen atom, an oxygen atom, and a sulfur atom. , Preferably at least one selected from silicon atoms and selenium atoms. Similarly, a “heteroaromatic ring” is a ring containing at least one heteroatom as a ring-forming atom, and the heteroatom includes a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, and a selenium atom. One or more selected are preferable.

In the present specification, the “substituted or unsubstituted carbazolyl group” means the following carbazolyl group,

And a substituted carbazolyl group having an optional substituent with respect to the above group.
The substituted carbazolyl group may be condensed by bonding arbitrary substituents to each other, and may contain a heteroatom such as a nitrogen atom, an oxygen atom, a silicon atom and a selenium atom, and the bonding position is It may be any of 1st to 9th positions. Specific examples of such a substituted carbazolyl group include the groups shown below.

In the present specification, “substituted or unsubstituted dibenzofuranyl group” and “substituted or unsubstituted dibenzothiophenyl group” include the following dibenzofuranyl group and dibenzothiophenyl group,

And a substituted dibenzofuranyl group and a substituted dibenzothiophenyl group further having an optional substituent with respect to the above group.
In addition, the substituted dibenzofuranyl group and the substituted dibenzothiophenyl group may be bonded together by arbitrary substituents and may be condensed, and include a hetero atom such as a nitrogen atom, an oxygen atom, a silicon atom, and a selenium atom. The bonding position may be any of the 1st to 8th positions.
Specific examples of such a substituted dibenzofuranyl group and a substituted dibenzothiophenyl group include the following groups.

[In the above formula, X represents an oxygen atom or a sulfur atom, Y represents an oxygen atom, a sulfur atom, NH, NR ^a (R ^a is an alkyl group or an aryl group), CH ₂ , or CR ^b ₂ ( R ^b represents an alkyl group or an aryl group. ]

An optional substituent that can be “substituted” in the description of “substituted or unsubstituted” includes an alkyl group having 1 to 50 carbon atoms (preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms); A cycloalkyl group having 3 to 50 (preferably 3 to 10, more preferably 3 to 8, more preferably 5 or 6); 6 to 50 ring carbon atoms (preferably 6 to 25, more preferably 6 to 18). An aryl group of 7 to 51 (preferably 7 to 30, more preferably 7 to 20) having an aryl group having 6 to 50 ring forming carbon atoms (preferably 6 to 25, more preferably 6 to 18). An aralkyl group; an amino group; an alkyl group having 1 to 50 carbon atoms (preferably 1 to 18, more preferably 1 to 8) and a ring forming carbon number 6 to 50 (preferably 6 to 25, more preferably 6 to 18). ) Aryl group A mono- or di-substituted amino group having a selected substituent; an alkoxy group having an alkyl group having 1 to 50 carbon atoms (preferably 1 to 18 and more preferably 1 to 8); 6 to 50 ring carbon atoms (preferably Is an aryloxy group having an aryl group of 6 to 25, more preferably 6 to 18); an alkyl group having 1 to 50 carbon atoms (preferably 1 to 18, more preferably 1 to 8) and a ring forming carbon number of 6 to A mono-, di- or tri-substituted silyl group having a substituent selected from 50 (preferably 6 to 25, more preferably 6 to 18) aryl groups; 5 to 50 ring atoms (preferably 5 to 24, More preferably 5 to 13) heteroaryl group; a haloalkyl group having 1 to 50 carbon atoms (preferably 1 to 18 and more preferably 1 to 8); halogen atom (fluorine atom, chlorine atom, bromine) A cyano group; a nitro group; an alkyl group having 1 to 50 carbon atoms (preferably 1 to 18, more preferably 1 to 8) and a ring forming carbon number 6 to 50 (preferably 6 to 25, more). A sulfonyl group having a substituent selected from an aryl group of preferably 6 to 18); an alkyl group having 1 to 50 carbon atoms (preferably 1 to 18, more preferably 1 to 8) and a ring forming carbon number of 6 to 50 ( A disubstituted phosphoryl group having a substituent selected from an aryl group of preferably 6 to 25, more preferably 6 to 18); an alkylsulfonyloxy group; an arylsulfonyloxy group; an alkylcarbonyloxy group; an arylcarbonyloxy group; Group; zinc-containing group; tin-containing group; silicon-containing group; magnesium-containing group; lithium-containing group; hydroxy group; At least one selected from the group consisting of a carbonyl group; a carboxyl group; a vinyl group; a (meth) acryloyl group; an epoxy group; and an oxetanyl group is preferable.
These substituents may be further substituted with the above-mentioned arbitrary substituents. In addition, these substituents may be bonded to each other to form a ring.
In addition, “unsubstituted” in the description of “substituted or unsubstituted” means that a hydrogen atom is bonded without being substituted by these substituents.

Among the above substituents, more preferably, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms (preferably 1 to 18, more preferably 1 to 8), substituted or unsubstituted ring carbon atoms having 3 to 50 carbon atoms. (Preferably 3 to 10, more preferably 3 to 8, more preferably 5 or 6) cycloalkyl group, substituted or unsubstituted 6 to 50 ring carbon atoms (preferably 6 to 25, more preferably 6 to 6) 18) an aryl group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms (preferably 1 to 18, more preferably 1 to 8), and a substituted or unsubstituted ring carbon atom number 6 to 50 (preferably 6). A mono- or di-substituted amino group having a substituent selected from an aryl group of ˜25, more preferably 6-18, a substituted or unsubstituted ring atom number of 5-50 (preferably 5-24, Ri is preferably a heteroaryl group of from 5 to 13), a halogen atom, a cyano group.

In this specification, it is possible to arbitrarily select a rule that is preferable, and it can be said that a combination of rules that are preferable is more preferable.

[Compound]
The compound of the present invention useful as a material for an organic electroluminescence device is represented by the following general formula (1).

[In the formula (1), X ¹ to X ¹⁰ each represent C (R ^A1 ) to C (R ^A10 ) or a nitrogen atom, and at least two of X ¹ to X ¹⁰ are C (R ^A1 ) to C (R ^A10 )
However, at least two selected from R ^A1 to R ^A10 are bonded to each other to form a saturated or unsaturated ring.
R ^A1 to R ^A10 each independently represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted group Aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted arylthio group, substituted or unsubstituted silyl group, substituted or unsubstituted An amino group or a group represented by the following general formula (2).
However, at least one of R ^A1 to R ^A10 (including a group bonded to a carbon atom constituting the ring at a position where each ring is bonded to each other) is represented by the following general formula (2) It is group represented by these.

(In Formula (2), Z shows an oxygen atom, a sulfur atom, or a selenium atom.
L ¹ is a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms, or a bond of 2 to 4 of these groups Is a divalent group.
Ar ¹ and Ar ² are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, and Ar ¹ And Ar ² may be bonded to each other to form a ring. )]

In the general formula (1), X ¹ to X ¹⁰ each represent C (R ^A1 ) to C (R ^A10 ) or a nitrogen atom.
That is, X ¹ is C (R ^A1 ) or a nitrogen atom, X ² is C (R ^A2 ) or a nitrogen atom, X ³ is C (R ^A3 ) or a nitrogen atom, X ⁴ is C (R ^A4 ) or a nitrogen atom, X ⁵ is C (R ^A5 ) or a nitrogen atom, X ⁶ is C (R ^A6 ) or a nitrogen atom, X ⁷ is C (R ^A7 ) or a nitrogen atom, X ⁸ is C (R ^A8 ) or a nitrogen atom, X ⁹ Is C (R ^A9 ) or a nitrogen atom, and X ¹⁰ is C (R ^A10 ) or a nitrogen atom.

In the general formula (1), at least two selected from R ^A1 to R ^A10 are bonded to each other to form a saturated or unsaturated ring.
That is, in the general formula (1), at least two of X ¹ to X ¹⁰ are any one of C (R ^A1 ) to C (R ^A10 ), and at least 2 selected from R ^A1 to R ^A10 Are joined together to form a saturated or unsaturated ring. Therefore, the number of nitrogen atoms in X ¹ to X ¹⁰ is 0 to 8. The number of nitrogen atoms in X ¹ to X ¹⁰ is preferably 0 to 3, more preferably 0 to 2.

In the general formula (1), for example, when X ¹ is a nitrogen atom and X ² to X ¹⁰ are C (R ^A2 ) to C (R ^A10 ), respectively, they are selected from R ^A2 to R ^A10 At least two of them are bonded to each other to form the above ring.
In forming the ring, for example, the following embodiments [I] and [II] are considered.
(I) ^{X 1} and ^X 2, ^{X 2} and ^X 3, ^{X 3} and ^X 4, ^{X 4} and ^X 5, ^{X 5} and ^X 6, ^{X 6} and ^X 7, ^{X 7} and ^X 8, ^{X 8} and ^{X 9} , X ⁹ and X ¹⁰ , and at least one selected from X ¹⁰ and X ¹ are both groups selected from C (R ^A1 ) to C (R ^A10 ), and the selected R ^A1 to R ^A10 Together form a saturated or unsaturated ring.
[II] Two selected from X ¹ to X ¹⁰ other than the group listed in [I] above are both groups selected from C (R ^A1 ) to C (R ^A10 ), and this selected R ^A1 Two of R ^A10 are bonded to each other to form a saturated or unsaturated ring.
Examples of the compound in which the ring of the above embodiment [I] is formed include, for example, X ¹ and X ² are C (R ^A1 ) and C (R ^A10 ) (wherein X ³ to X ¹⁰ are each C (R ^A3 ) to C (R ^A10 ) or a nitrogen atom), and two of R ^A1 and R ^A2 are bonded to each other to form a saturated or unsaturated ring.
Examples of the compound in which the ring of the above embodiment [II] is formed include, for example, X ¹ and X ¹⁰ are C (R ^A1 ) and C (R ^A10 ) (wherein X ² to X ⁹ are C (R ^A2 ) to C (R ^A9 ) or a nitrogen atom), and two of R ^A1 and R ^A10 are bonded to each other to form a saturated or unsaturated ring.
Note that at least one such ring may be formed, and two or more such rings may be formed.

In one embodiment of the compound of the present invention, X ¹ and X ² , X ² and X ³ , X ³ and X ⁴ , X ⁴ and X ⁵ are compounds in which the ring of the embodiment of [I] is formed. At least one selected from X ⁵ and X ⁶ , X ⁶ and X ⁷ , X ⁷ and X ⁸ , X ⁸ and X ⁹ , X ⁹ and X ¹⁰ , and X ¹⁰ and X ¹ is both C (R ^A1 ) To C (R ^A10 ), and the selected two of R ^A1 to R ^A10 are preferably bonded to each other to form a saturated or unsaturated ring.

The saturated or unsaturated ring includes a substituted or unsubstituted aromatic ring having 6 to 40 (preferably 6 to 25, more preferably 6 to 18) ring-forming carbon atoms, a substituted or unsubstituted ring-forming atom number of 6 to 40 (preferably 6 to 25, more preferably 6 to 18) aromatic hetero ring, saturated with 6 to 40 (preferably 6 to 25, more preferably 6 to 18) ring-forming carbon atoms substituted or unsubstituted Or an unsaturated aliphatic ring and a saturated or unsaturated aliphatic hetero ring having 6 to 40 (preferably 6 to 25, more preferably 6 to 18) substituted or unsubstituted ring-forming atoms. A ring is preferred. These rings may be rings in which the conjugated system is broken.

In one embodiment of the compound of the present invention, a compound in which X ¹ to X ¹⁰ in the general formula (1) are C (R ^A1 ) to C (R ^A10 ), respectively, or a group represented by X ¹ to X ¹⁰ A compound in which at least one is a nitrogen atom is preferred.
In at least one is a nitrogen atom the compound of X ¹ ~ ^{X ^10,} as the number of nitrogen atoms in the X 1 ^{~ X 10,} and preferably 1 to 3, more preferably 1 or 2.

R ^A1 to R ^A10 are as described above, and more preferable examples of R ^A1 to R ^A10 include independently a hydrogen atom, a halogen atom (a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, An atom is preferred), a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms (preferably 1 to 12, more preferably 1 to 8), a substituted or unsubstituted ring carbon number 3 to 20 (preferably Are 3 to 10, more preferably 3 to 8, more preferably 5 or 6) cycloalkyl groups, substituted or unsubstituted 6 to 30 ring carbon atoms (preferably 6 to 25, more preferably 6 to 18). Aryl groups, substituted or unsubstituted heteroaryl groups having 5 to 30 (preferably 5 to 24, more preferably 5 to 13) ring-forming atoms, substituted or unsubstituted carbon atoms of 1 to 2 (Preferably 1 to 12, more preferably 1 to 8) alkoxy group, substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms (preferably 6 to 25, more preferably 6 to 18), substituted Alternatively, an unsubstituted alkylthio group having 1 to 20 carbon atoms (preferably 1 to 12, more preferably 1 to 8), or a substituted or unsubstituted ring carbon atom number 6 to 30 (preferably 6 to 25, more preferably 6). To 18) an arylthio group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, or a group represented by the above general formula (2).

The “substituted or unsubstituted silyl group” that can be selected as R ^A1 to R ^A10 is preferably a “group represented by —Si (R ^C1 ) (R ^C2 ) (R ^C3 )”.
The “substituted or unsubstituted amino group” that can be selected as R ^A1 to R ^A10 is preferably a “group represented by —N (R ^D1 ) (R ^D2 )”.
R ^C1 to R ^C3 and R ^D1 to R ^D2 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms (preferably 1 to 12, more preferably 1 to 8), A substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms (preferably 3 to 10, more preferably 3 to 8, more preferably 5 or 6), substituted or unsubstituted ring carbon atoms 6 to 50 An aryl group (preferably 3 to 25, more preferably 6 to 18), or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms (preferably 5 to 24, more preferably 5 to 13). is there.
In addition, when R ^C1 to R ^{C3 of the} “group represented by —Si (R ^C1 ) (R ^C2 ) (R ^C3 )” are all hydrogen atoms, the group is “unsubstituted silyl group (—SiH ₃ ) ”. The group in the case where R ^D1 to R ^D2 of the group represented by —N (R ^D1 ) (R ^D2 ) are all hydrogen atoms is “unsubstituted amino group (—NH ₂ )”.

Specific examples of each group that can be selected as R ^A1 to R ^A10 , R ^C1 to R ^C3, and R ^D1 to R ^D2 are shown below.

Examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group (including isomers), and hexyl. Groups (including isomers), heptyl groups (including isomers), octyl groups (including isomers), nonyl groups (including isomers), decyl groups (including isomers), undecyl groups (including isomers) ), Dodecyl group (including isomers), tridecyl group, tetradecyl group, octadecyl group and the like.

Examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, and the like.

Examples of the aryl group include phenyl group, naphthyl group (1-naphthyl group, 2-naphthyl group), anthryl group (1-anthryl group, 2-anthryl group, etc.), biphenyl group, terphenyl group, benzo [a Anthryl group, phenanthryl group (1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 9-phenanthryl group, etc.), benzo [c] phenanthryl group, fluorenyl group, benzo [a] fluorenyl group, benzo [b] Fluorenyl group, benzo [c] fluorenyl group, dibenzofluorenyl group, picenyl group, tetracenyl group, pentacenyl group, pyrenyl group, chrysenyl group, benzo [g] chrycenyl group, s-indacenyl group, as-indacenyl group, fluorane Tenenyl group, benzo [a] fluoranthenyl group, benzo [b Fluoranthenyl group, benzo [j] fluoranthenyl group, a benzo [k] fluoranthenyl group, triphenylenyl group, benzo [b] triphenylenyl group, a perylenyl group, and a coronenyl group or dibenzo anthryl group.

Examples of the heteroaryl group include pyrrolyl group, pyridyl group (2-pyridyl group and the like), imidazopyridyl group, bipyridyl group, pyrazolyl group, triazolyl group, tetrazolyl group, indolyl group, isoindolyl group, phenanthryl group and carbazolyl group [ 9-substituted-3-carbazolyl group and the like. The substituent at the 9-position is an alkyl group having 1 to 10 carbon atoms (preferably 1 to 6), an aryl group having 6 to 30 ring carbon atoms (preferably 6 to 14 carbon atoms), or 5 to 30 ring atoms. (Preferably 5 to 14) heteroaryl group. A monovalent nitrogen-containing heteroaryl group such as: furanyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group (2-dibenzofuranyl group etc.), oxazolyl group, oxadiazolyl group, benzoxazolyl group, Monovalent oxygen-containing heteroaryl groups such as benzonaphthofuranyl group and dinaphthofuranyl group; benzothiophenyl group, dibenzothiophenyl group (2-dibenzothiophenyl group etc.), thiophenyl group, thiazolyl group, thiadiazolyl group, benzothiazolyl group, And monovalent sulfur-containing heteroaryl groups such as a benzonaphthothiophenyl group and a dinaphthothiophenyl group.

Examples of the alkoxy group include groups in which the alkyl group portion is the alkyl group, and specific examples include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, and an octyl group. An oxy group, a nonyloxy group, a decyloxy group, etc. are mentioned.
As said aryloxy group, the group whose aryl group site | part is the said aryl group is mentioned, Specifically, a phenoxy group, a biphenyloxy group, etc. are mentioned.

Examples of the alkylthio group include groups in which the alkyl group moiety is the alkyl group, and specific examples include a methylthio group and an ethylthio group.
As said arylthio group, the group whose aryl group site | part is the said aryl group is mentioned, Specifically, a phenylthio group, a biphenylthio group, etc. are mentioned.

In the general formula (1), the compound of the present invention includes R ^A1 to R ^A10 (including a group bonded to a carbon atom constituting the ring at a position where they are bonded to each other to form a ring). At least one of is a group represented by the general formula (2).
In the compound of the present invention, two compounds selected from R ^A1 to R ^A10 in the general formula (1) are bonded to each other to form a saturated or unsaturated ring, as described above. In the parentheses above, it is explained that the group bonded to the formed ring may be a group represented by the general formula (2).
For example, ^{X 1} and ^{X 2} are each a C ^{(R A1)} and C ^{(R ^A2),} Taking the case where the ^{R A1} and ^{R A2} are bonded to form a ring as an ^{example, R A1} and R ^The group represented by the general formula (2) is bonded to the carbon atom constituting the ring formed by bonding with ^A2 , or any one of R ^A3 to R ^A10 is the above general formula ( It becomes group represented by 2).
In addition, as one aspect | mode of the compound of this invention, the compound which has only one group represented by the said General formula (2) is preferable.

In the general formula (2), Z represents an oxygen atom, a sulfur atom, or a selenium atom, preferably an oxygen atom or a sulfur atom, and more preferably an oxygen atom.

L ¹ in the general formula (2) represents a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms, or these Is a divalent group in which 2 to 4 groups are bonded.
In addition, “single bond” may be generally referred to as “direct bond” in other words.

The arylene group that can be selected as L ¹ has 6 to 30 ring-forming carbon atoms, preferably 6 to 20, more preferably 6 to 14, and still more preferably 6 to 12.
Examples of the arylene group that can be selected as L ¹ include a phenylene group (1,4-phenylene group, etc.), a naphthylene group (1,4-naphthylene group, 1,5-naphthylene group, etc.), and an anthrylene group (9,9). 10-anthrylene group, etc.), biphenylylene group, terphenylylene group, benzoanthrylene group, phenanthrylene group, benzophenanthrylene group, fluorenylene group (2,7-fluorenylene group, etc.), benzofluorenylene group, dibenzofluorenylene group , Picenylene group, tetrasenylene group, pentasenylene group, pyrenylene group, chrysenylene group, benzocrisenylene group, s-indacenylene group, as-indacenylene group, fluoranthenylene group, benzofluoranthenylene group, peryleneylene group, coronenylene group and dibenzo Anthracenylene group, etc. Is mentioned.
The above arylene group may be an arylene group having a substituent, for example, a 9,9-disubstituted fluorenylene group (9,9-dimethyl-2,7-fluorenylene group, 9,9-diphenyl). -2,7-fluorenylene group, or 9,9-di (trimethylsilyl) -2,7-fluorenylene group is preferable).

The number of ring-forming atoms of the heteroarylene group that can be selected as L ¹ is 5 to 30, preferably 5 to 20, more preferably 5 to 14, and still more preferably 5 to 12.
Examples of the heteroarylene group that can be selected as L ¹ include pyrrolylene group, pyridylene group (2,5-pyridylene group, etc.), imidazopyridylene group, pyrazolylene group, triazolylene group, tetrazolylene group, indoleylene group, isoindoleylene group, and the like. Groups and divalent nitrogen-containing heteroarylene groups such as carbazolylene groups; furanylene groups, benzofuranylene groups, isobenzofuranylene groups, dibenzofuranylene groups (2,8-dibenzofuranylene groups, etc.), oxazolylene groups, oxadiazolylene groups Divalent oxygen-containing heteroarylene groups such as benzoxazolylene group, benzonaphthofurylene group and dinaphthofurylene group; thiophenylene group, benzothiophenylene group, dibenzothiophenylene group (2,8-dibenzothiophenylene group) Group), thiazolylene group, thia And divalent sulfur-containing heteroarylene groups such as a diazorylene group, a benzothiazolylene group, a benzonaphthothiophenylene group, and a dinaphthothiophenylene group.
The above-described heteroarylene group may be a heteroarylene group having a substituent, for example, a 9-substituted-3,6-carbazolylene group (the 9th-position substituent has 1 to 10 carbon atoms (preferably Is preferably an alkyl group having 1 to 6), an aryl group having 6 to 30 (preferably 6 to 14) ring carbon atoms, or a heteroaryl group having 5 to 30 (preferably 5 to 14) ring atoms. You can also choose.

L ¹ may be a divalent group formed by bonding 2 to 4 of these groups (arylene group and / or heteroarylene group). The divalent group is preferably a divalent group formed by bonding 2 to 4 groups selected from the group consisting of the following groups.

[In the above divalent group, any carbon atom that may have a substituent may have a substituent. ]

As specific divalent groups, the following groups are preferred.

Among these, L ¹ is preferably a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 30 ring carbon atoms. More preferably, it is an unsubstituted arylene group having 6 to 30 ring carbon atoms, more preferably a substituted or unsubstituted arylene group having 6 to 14 ring carbon atoms, and a substituted or unsubstituted phenylene group is Even more preferred.

In the general formula (2), Ar ¹ and Ar ² are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a heteroaryl group having 5 to 30 ring atoms. Ar ¹ and Ar ² may be bonded to each other to form a ring.

The number of ring-forming carbon atoms of the aryl group that can be selected as Ar ¹ and Ar ² is 6 to 30, preferably 6 to 20, more preferably 6 to 14, and still more preferably 6 to 12.
Examples of the aryl group that can be selected as Ar ¹ and Ar ² include phenyl group, naphthyl group (1-naphthyl group, 2-naphthyl group), anthryl group (1-anthryl group, 2-anthryl group, etc.), biphenyl, and the like. Group, terphenyl group, benzo [a] anthryl group, phenanthryl group (1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 9-phenanthryl group, etc.), benzo [c] phenanthryl group, fluorenyl group, benzo [ a] fluorenyl group, benzo [b] fluorenyl group, benzo [c] fluorenyl group, dibenzofluorenyl group, picenyl group, tetracenyl group, pentacenyl group, pyrenyl group, chrysenyl group, benzo [g] chrysenyl group, s-indacenyl Group, as-indacenyl group, fluoranthenyl group, benzo [a Fluoranthenyl group, benzo [b] fluoranthenyl group, benzo [j] fluoranthenyl group, benzo [k] fluoranthenyl group, triphenylenyl group, benzo [b] triphenylenyl group, perylenyl group, coronenyl group or dibenzoan And a tolyl group.
The aryl group described above may further be an aryl group having a substituent, such as a 9,9-disubstituted fluorenyl group (9,9-dimethyl-2-fluorenyl group, 9,9-diphenyl-2). -Fluorenyl group, 9,9-di (trimethylsilyl) -2-fluorenyl group and the like) can also be selected.

The number of ring-forming atoms of the heteroaryl group that can be selected as Ar ¹ and Ar ² is 5 to 30, preferably 5 to 20, more preferably 5 to 14, and still more preferably 5 to 12.
Examples of the heteroaryl group that can be selected as Ar ¹ and Ar ² include, for example, pyrrolyl group, pyridyl group (2-pyridyl group and the like), imidazopyridyl group, bipyridyl group, pyrazolyl group, triazolyl group, tetrazolyl group, indolyl group, Monovalent nitrogen-containing heteroaryl groups such as isoindolyl group, phenanthroyl group and carbazolyl group; furanyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group (2-dibenzofuranyl group etc.), oxazolyl group, oxadiazolyl group Monovalent oxygen-containing heteroaryl groups such as benzoxazolyl group, benzonaphthofuranyl group and dinaphthofuranyl group; benzothiophenyl group, dibenzothiophenyl group (such as 2-dibenzothiophenyl group), thiophenyl group, thiazolyl group , Thiadiazolyl group, benzo Azolyl group, monovalent sulfur-containing heteroaryl groups such as benzo-naphthoquinone Tochio phenyl and Gina shift thiophenyl group and the like.
The heteroaryl group described above may be a heteroaryl group having a substituent. For example, a 9-substituted-3-carbazolyl group (the substituent at the 9-position has 1 to 10 carbon atoms (preferably 1). To 6) an alkyl group, an aryl group having 6 to 30 ring carbon atoms (preferably 6 to 14) or a heteroaryl group having 5 to 30 ring atoms (preferably 5 to 14) is also selected. Can do.

Ar ¹ and Ar ² may be bonded to each other to form a ring.
When forming the ring structure, examples of the group represented by the general formula (2) include the following groups.

In one embodiment of the compound of the present invention, at least one of Ar ¹ and Ar ² is preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and both Ar ¹ and Ar ² are More preferably, it is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and both Ar ¹ and Ar ² are substituted or unsubstituted aryl groups having 6 to 14 ring carbon atoms. More preferably, Ar ¹ and Ar ² are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenylyl group, or a substituted or unsubstituted fluorenyl group. It is even more preferable.

As one embodiment of the compound of the present invention, in the general formula (1), X ¹ and X ² , X ² and X ³ , X ³ and X ⁴ , X ⁴ and X ⁵ , X ⁵ and X ⁶ , X ⁶ and At least one set selected from X ⁷ , X ⁷ and X ⁸ , X ⁸ and X ⁹ , X ⁹ and X ¹⁰ , and X ¹⁰ and X ¹ are both selected from C (R ^A1 ) to C (R ^A10 ) ^A compound in which two selected from R ^A1 to R ^A10 are bonded to each other to form any of the rings represented by the following general formulas (3-a) to (3-e) (hereinafter, , Also referred to as “the compound of the first aspect of the present invention”).

For example, when a selected pair is X ¹ and X ² and X ¹ and X ² are C (R ^A1 ) and C (R ^A2 ), respectively (other X ³ to X ¹⁰ are independent of each other) The corresponding C (R ^A3 ) to C (R ^A10 ) or a nitrogen atom), and R ^A1 and R ^A2 are bonded to each other to form the above general formulas (3-a) to (3-e The compound that forms any one of the rings represented by) is included in the compound of the first aspect of the present invention.
The compound of the first aspect of the present invention may be a compound having only one of the rings represented by the general formulas (3-a) to (3-e), It may be a compound having two or more of any of the rings represented by 3-a) to (3-e).

In the above formulas (3-a) to (3-e), * represents a bond part with a carbon atom, and Y represents —C (R ^B29 ) (R ^B30 ) —, —N (R ^B31 ) —, —Si (R ^B32 ) (R ^B33 ) —, —O—, or —S— is shown.

R ^B1 to R ^B33 each independently represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted group Heteroaryl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted arylthio group, substituted or unsubstituted silyl group, substituted or unsubstituted An amino group or a group represented by the general formula (2).

R ^B1 to R ^B33 are as described above, and more preferable R ^B1 to R ^B33 are each independently a hydrogen atom, a halogen atom (a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, An atom is preferred), a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms (preferably 1 to 12, more preferably 1 to 8), a substituted or unsubstituted ring carbon number 3 to 20 (preferably Are 1 to 10, more preferably 3 to 8, more preferably 5 or 6) cycloalkyl group, substituted or unsubstituted 6 to 30 ring carbon atoms (preferably 6 to 25, more preferably 6 to 18). Aryl groups, substituted or unsubstituted heteroaryl groups having 5 to 30 (preferably 5 to 24, more preferably 5 to 13) ring-forming atoms, substituted or unsubstituted carbon atoms of 1 to 2 (Preferably 1 to 12, more preferably 1 to 8) alkoxy group, substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms (preferably 6 to 25, more preferably 6 to 18), substituted Alternatively, an unsubstituted alkylthio group having 1 to 20 carbon atoms (preferably 1 to 12, more preferably 1 to 8), or a substituted or unsubstituted ring carbon atom number 6 to 30 (preferably 6 to 25, more preferably 6). To 18) an arylthio group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, or a group represented by the general formula (2).

^As the "substituted or unsubstituted silyl group" may be selected as R B1 ^{~ R B33} is ^- preferably ^{"Si (R C1) (R C2} ) groups represented by ^{(R ^C3)",} ^{R B1} ~ The “substituted or unsubstituted amino group” that can be selected as R ^B33 is preferably a “group represented by —N (R ^D1 ) (R ^D2 )” (R ^C1 to R ^C3 and R ^D1 to R ^D2 are , As described above).

Examples of more specific groups of the above-mentioned groups (alkyl group, cycloalkyl group, etc.) that can be selected as R ^B1 to R ^B33 are selected as R ^A1 to R ^{A10 in} the above general formula (1). Examples of each group to be obtained include the same groups as those exemplified.

In the compound of the first aspect of the present invention, at least one of R ^A1 to R ^A10 in the general formula (1) and R ^B1 to R ^{B28 in} the general formulas (3-a) to (3-e) Is a group represented by the general formula (2).
In addition, in the compound of the 1st aspect of this invention, it is preferable that it is a compound which has only 1 group represented by the said General formula (2).

Further, among the compounds of the first aspect of the present invention, compounds represented by any one of the following general formulas (1-1) to (1-9) (hereinafter also referred to as “compound of the second aspect of the present invention”). ) Is more preferable.

In the above general formulas (1-1) to (1-9), X ¹ to X ¹⁰ each represent C (R ^A1 ) to C (R ^A10 ) or a nitrogen atom.
R ^A1 to R ^A10 are the same as described above with respect to the general formula (1).
Y represents —C (R ^B29 ) (R ^B30 ) —, —N (R ^B31 ) —, ^—Si (R ^B32 ) (R ^B33 ) —, —O—, or —S—.
R ^B1 to R ^B33 and R ^{B1 ′} to R ^{B4 ′} are each independently a hydrogen atom, halogen atom, cyano group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted Aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted arylthio group, substituted or unsubstituted A silyl group, a substituted or unsubstituted amino group, or a group represented by the general formula (2).

R ^B1 to R ^B33 and R ^{B1 ′} to R ^{B4 ′} are as described above, and more preferable R ^B1 to R ^B33 and R ^{B1 ′} to R ^{B4 ′} are each independently a hydrogen atom, a halogen atom, A cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, substituted or An unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, a substituted or unsubstituted silyl group, a substituted or unsubstituted atom; It is a mino group or a group represented by the general formula (2).

The “substituted or unsubstituted silyl group” that can be selected as R ^B1 to R ^B33 and R ^{B1 ′} to R ^{B4 ′} is represented by “—Si (R ^C1 ) (R ^C2 ) (R ^C3 )”. A “substituted or unsubstituted amino group” that can be selected as R ^B1 to R ^B33 and R ^{B1 ′} to R ^{B4 ′} is represented by “—N (R ^D1 ) (R ^D2 )”. (R ^C1 to R ^C3 and R ^D1 to R ^D2 are as defined above).

Examples of more specific groups of the above-described groups (alkyl group, cycloalkyl group, etc.) that can be selected as R ^B1 to R ^B33 and R ^{B1 ′} to R ^{B4 ′} include those in the above general formula (1). Examples thereof include the same groups as those exemplified as each group that can be selected as R ^A1 to R ^A10 .

In the compound of the second aspect of the present invention, at least one of R ^A1 to R ^A10 , R ^B1 to R ^B28 , and R ^{B1 ′} to R ^{B4 ′} in the above formulas (1-1) to (1-9) is It is group represented by the said General formula (2).
As one embodiment of the compound of the second embodiment of the present invention, only one of R ^A1 to R ^A10 , R ^B1 to R ^B28 , and R ^{B1 ′} to R ^{B4 ′} is represented by the general formula (2). It is preferred that The compound represented by any one of the general formulas (1-1) to (1-9) is preferably a compound having only one group represented by the general formula (2).

Among the compounds according to the second aspect of the present invention, compounds in which X ¹ to X ^{10 in the} general formulas (1-1) to (1-9) are C (R ^A1 ) to C (R ^A10 ), respectively ( Hereinafter, also referred to as “the compound of the third aspect of the present invention”, or a compound in which at least one of X ¹ to X ^{10 in} the general formulas (1-1) to (1-9) is a nitrogen atom (hereinafter referred to as “the compound of the third aspect of the present invention”) (It is also referred to as “the compound of the fourth aspect of the present invention”).
In addition, in the compound of the 3rd aspect and 4th aspect of this invention, it is preferable that it is a compound which has only one group represented by the said General formula (2).

That is, the compound of the third aspect of the present invention is a compound in which none of X ¹ to X ^{10 in the} general formulas (1-1) to (1-9) has a nitrogen atom.
The compound according to the third aspect of the present invention is preferably a compound represented by any one of the following general formulas (1-1A) to (1-9A).

In the general formulas (1-1A) to (1-9A), R ^A1 to R ^A10 are the same as those described above for the general formula (1), and R ^B1 to R ^B28 , R ^{B1 ′} to R ^{B4 'And} Y are the same as described above with respect to the general formulas (1-1) to (1-9).

At least one of R ^A1 to R ^A10 , R ^B1 to R ^B28 , and R ^{B1 ′} to R ^{B4 ′ in} the general formulas (1-1A) to (1-9A) is represented by the general formula (2). Group.
As one embodiment of the compound of the third embodiment of the present invention, only one of R ^A1 to R ^A10 , R ^B1 to R ^B28 , and R ^{B1 ′} to R ^{B4 ′} is represented by the general formula (2). It is preferred that The compound represented by any one of the general formulas (1-1A) to (1-9A) is preferably a compound having only one group represented by the general formula (2).

In the general formulas (1-1A), (1-3A), and (1-9A), R ^A1 and R ^A4 in each formula are a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. Group, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, substituted or unsubstituted heteroaryl having 5 to 30 ring atoms Group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, substituted or unsubstituted It is preferably a substituted arylthio group having 6 to 30 ring carbon atoms or a group represented by the general formula (2), and is a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. A substituted or unsubstituted ring atoms 5-30 heteroaryl group, or, more preferably a group represented by the general formula (2).

Among the compounds represented by the general formulas (1-1A) to (1-9A), the compound represented by the general formula (1-1A) is preferable.
Further, among the compounds represented by the general formula (1-1A), compounds having only one group represented by the general formula (2) are more preferable, and the following general formulas (1-1A-i) to The compound represented by any of (1-1A-iii) is more preferable.

In the above formulas (1-1A-i) to (1-1A-iii), L ¹ , Ar ¹ , Ar ² , and Z are the same as described above with respect to the general formula (2).
R ^B1 to R ^B4 are the same as those described above with respect to the general formula (1-1).
R ^a1 , R ^a4 to R ^a10 and R ^b1 to R ^b4 each independently represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, substituted or unsubstituted Substituted aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted arylthio group, substituted or unsubstituted A substituted silyl group or a substituted or unsubstituted amino group.
However, in the above formulas (1-1A-i) to (1-1A-iii), all of R ^a1 , R ^a4 to R ^a10 and R ^b1 to R ^b4 are represented by the general formula (2). Not a group.

R ^a1 , R ^a4 to R ^a10 , and R ^b1 to R ^b4 are the above-described R ^A1 , R ^A4 to R ^A4 , except that the group represented by the general formula (2) is not selected. The same as the definition of R ^A10 and R ^B1 to R ^B4 . Examples of more specific groups of the above groups that can be selected as R ^a1 , R ^a4 to R ^a10 , and R ^b1 to R ^b4 include R ^A1 to R ^{A10 in} the above general formula (1). The same groups as those exemplified as each group which can be selected as

In the general formula (1-1A-i), R ^a4 represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclocarbon having 3 to 20 ring carbon atoms. An alkyl group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, It is a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, or a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms. And more preferably a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms. A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms is more preferable.

In the general formulas (1-1A-ii) to (1-1A-iii), R ^a1 and R ^a4 in each formula are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms. Group, substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, substituted or unsubstituted heteroaryl having 5 to 30 ring atoms Group, substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, or substituted or unsubstituted It is preferably an unsubstituted arylthio group having 6 to 30 ring carbon atoms, a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted ring former. It is more preferably a heteroaryl group having 5 to 30 members, and further preferably a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

The compound according to the fourth aspect of the present invention is a compound in which at least one of X ¹ to X ^{10 in} the formulas (1-1) to (1-9) is a nitrogen atom.
In the compound of the fourth aspect of the present invention, the number of nitrogen atoms in X ¹ to X ¹⁰ is 1 or more, preferably 1 to 3, more preferably 1 or 2.
In the formulas (1-1) to (1-9), at least one of X ¹ , X ³ and X ⁴ is preferably a nitrogen atom.
Specifically, the compound according to the fourth aspect of the present invention is preferably a compound represented by any one of the following general formulas (1-1B) to (1-5B).

In the above formulas (1-1B) to (1-5B), R ^A2 , R ^A3 , R ^A5 to R ^A10 are the same as those described above for the general formula (1), and R ^B1 to R ^B4 , R ^{B1 ′} to R ^{B4 ′} , R ^B17 to R ^B20 and Y are the same as described above with respect to the general formulas (1-1) to (1-9).

At least one of R ^A2 , R ^A3 , R ^A5 to R ^A10 , R ^B1 to R ^B4 , R ^B17 to R ^B20 , and R ^{B1 ′} to R ^{B4 ′ in} the above formulas (1-1B) to (1-5B) One of the groups represented by the general formula (2) is R ^A2 , R ^A3 , R ^A5 to R ^A10 , R ^B1 to R ^B4 , R ^B17 to R ^B20 , and R ^{B1 ′} to R ^{B4 ′.} It is preferable that only one of these is a group represented by the general formula (2). The compound represented by any one of the above formulas (1-1B) to (1-5B) is preferably a compound having only one group represented by the general formula (2).

In the general formula (1-2B), R ^A2 and R ^A3 in the formula are a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted number of ring forming atoms. A 5-30 heteroaryl group is preferred.

The compound according to the fourth aspect of the present invention is preferably a compound represented by any one of the following general formulas (1-6B) to (1-9B).

In the above formulas (1-6B) to (1-8B), R ^A1 to R ^A7 and R ^A10 are the same as those described above for the general formula (1), and R ^B1 to R ^B4 are the same as the general formula. The same as the description above regarding (1-1) to (1-9).

In the above formulas (1-6B) to (1-8B), at least one of R ^A1 to R ^A7 , R ^A10 , and R ^B1 to R ^B4 is a group represented by the general formula (2). It is preferable that only one of R ^A1 to R ^A7 , R ^A10 , and R ^B1 to R ^B4 is a group represented by the general formula (2). The compound represented by any one of the above formulas (1-6B) to (1-8B) is preferably a compound having only one group represented by the general formula (2).

Among the compounds represented by any one of the general formulas (1-1B) to (1-8B), the compound represented by the general formula (1-1B) is preferable.
Among the compounds represented by the general formula (1-1B), compounds having only one group represented by the general formula (2) are more preferable, and the following general formula (1-1Bi) to The compound represented by any of (1-1B-iii) is more preferable.

In the above formulas (1-1B-i) to (1-1B-iii), L ¹ , Ar ¹ , Ar ² , and Z are the same as those described above for the general formula (2).
R ^a5 to R ^a10 and R ^b1 to R ^b4 each independently represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl. Group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted arylthio group, substituted or unsubstituted silyl Or a substituted or unsubstituted amino group.
However, none of R ^a5 to R ^a10 and R ^b1 to R ^{b4 in} the above formulas (1-1Bi) to (1-1B-iii) is a group represented by the general formula (2). .

R ^a5 to R ^a10 and R ^b1 to R ^b4 are the above-described R ^A5 to R ^A10 and R ^B1 except that the group represented by the general formula (2) is not selected. Same as the definition of ^{˜R B4} . Examples of more specific groups of the above-mentioned groups that can be selected as R ^a5 to R ^a10 and R ^b1 to R ^b4 are selected as R ^A1 to R ^{A10 in} the above general formula (1). Examples of each group to be obtained include the same groups as those exemplified.

Among the compounds represented by any one of the general formulas (1-1B-i) to (1-1B-iii), from the viewpoint of a material for an organic EL device that can further improve the luminous efficiency of the organic EL device, The compound represented by the general formula (1-1B-i) or (1-1B-ii) is preferable, and from the viewpoint of obtaining a material for an organic EL device that can further improve the life of the organic EL device, A compound represented by (1-1B-i) or (1-1B-iii) is preferred, and a compound represented by the general formula (1-1B-iii) is more preferred.

Specific examples of one embodiment of the compound of the present invention include the following compounds, but are not particularly limited thereto. In the following examples of specific compounds, cases where X in the general formula (2) is an oxygen atom are listed. Therefore, the oxygen atom which the group represented by Formula (2) in the structure of the following compounds has can be replaced with a sulfur atom or a selenium atom. Furthermore, in the following compounds, any carbon atom that may have a substituent may have a substituent.

[Organic electroluminescence materials]
The organic EL device material of the present invention is composed of the compound of the present invention described above.
The organic EL device material of the present invention may be composed of only one of the compounds of the present invention, or may be composed of two or more of the compounds of the present invention.
In addition, you may mix and use the organic EL element material of this invention for the well-known organic EL element material.

[Organic electroluminescence device]
Next, an embodiment of the organic EL element of the present invention will be described.
The organic EL device of the present invention has an organic thin film layer composed of a single layer or a plurality of layers including a light emitting layer between a cathode and an anode, and at least one of the organic thin film layers is a compound of the present invention (hereinafter referred to as “ By including the “organic EL element material of the present invention”), the light emission efficiency of the organic EL element is increased and low voltage driving is enabled.
As an example of the organic thin film layer containing the material for an organic EL device of the present invention, a hole transport zone (also referred to as a hole transport layer provided between the anode and the light emitting layer of the organic EL device. The term “hole transport zone” refers to the case where there is a single layer or a plurality of layers, and the electron transport zone (also referred to as an electron transport layer) provided between the cathode and the light emitting layer of the organic EL element. However, the term “electron transport zone” is used in the meaning of including one or a plurality of electron transport layers, and a light emitting layer, a space layer, a barrier layer, and the like.
Although not particularly limited, the organic EL device material of the present invention is preferably included in the electron transport zone.

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

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

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

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

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

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

(substrate)
The substrate is used as a support for the light emitting element. As the substrate, for example, glass, quartz, plastic, or the like can be used. Further, a flexible substrate may be used. The flexible substrate is a substrate that can be bent (flexible), and examples thereof include plastic substrates made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. . Moreover, an inorganic vapor deposition film can also be used.

(anode)
For the anode formed on the substrate, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a high work function (specifically, 4.0 eV or more). Specifically, for example, indium tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, and indium oxide containing zinc oxide. And graphene. In addition, gold (Au), platinum (Pt), a nitride of a metal material (for example, titanium nitride), or the like can be given.

(Hole transport zone)
The hole transport zone includes a substance having a high hole injection property and / or a high hole transport property.
Substances with high hole injection properties include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, Tungsten oxide, manganese oxide, or the like can be used.
4,4 ′, 4 ″ -tris (N, N-diphenylamino) triphenylamine (abbreviation: TDATA), 4,4 ′, 4 ″ -tris [N- (3- Methylphenyl) -N-phenylamino] triphenylamine (abbreviation: MTDATA), 4,4′-bis [N- (4-diphenylaminophenyl) -N-phenylamino] biphenyl (abbreviation: DPAB), 4,4 '-Bis (N- {4- [N'-(3-methylphenyl) -N'-phenylamino] phenyl} -N-phenylamino) biphenyl (abbreviation: DNTPD), 1,3,5-tris [N -(4-Diphenylaminophenyl) -N-phenylamino] benzene (abbreviation: DPA3B), 3- [N- (9-phenylcarbazol-3-yl) -N-phenylamino] -9-phenylcarbazo (Abbreviation: PCzPCA1), 3,6-bis [N- (9-phenylcarbazol-3-yl) -N-phenylamino] -9-phenylcarbazole (abbreviation: PCzPCA2), 3- [N- (1 And aromatic amine compounds such as -naphthyl) -N- (9-phenylcarbazol-3-yl) amino] -9-phenylcarbazole (abbreviation: PCzPCN1).
Polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used. For example, poly (N-vinylcarbazole) (abbreviation: PVK), poly (4-vinyltriphenylamine) (abbreviation: PVTPA), poly [N- (4- {N ′-[4- (4-diphenylamino)] Phenyl] phenyl-N′-phenylamino} phenyl) methacrylamide] (abbreviation: PTPDMA), poly [N, N′-bis (4-butylphenyl) -N, N′-bis (phenyl) benzidine] (abbreviation: Polymer compounds such as Poly-TPD). In addition, a polymer compound to which an acid such as poly (3,4-ethylenedioxythiophene) / poly (styrenesulfonic acid) (PEDOT / PSS), polyaniline / poly (styrenesulfonic acid) (PAni / PSS) is added is used. You can also.

In addition, an aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like, which is a substance having a high hole transport property, can be used in the hole transport zone. Specifically, 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB) and N, N′-bis (3-methylphenyl) -N, N′— Diphenyl- [1,1′-biphenyl] -4,4′-diamine (abbreviation: TPD), 4-phenyl-4 ′-(9-phenylfluoren-9-yl) triphenylamine (abbreviation: BAFLP), 4 , 4′-bis [N- (9,9-dimethylfluoren-2-yl) -N-phenylamino] biphenyl (abbreviation: DFLDPBi), 4,4 ′, 4 ″ -tris (N, N-diphenylamino) ) Triphenylamine (abbreviation: TDATA), 4,4 ′, 4 ″ -tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine (abbreviation: MTDATA), 4,4′-bis [N- (Spiro-9,9'-Biff Oren-2-yl) -N- phenylamino] biphenyl (abbreviation: BSPB) can be used aromatic amine compounds such as. The substances described here are mainly substances having a hole mobility of 10 −6 cm 2 / Vs or higher.
For the hole transport layer, carbazole derivatives such as CBP, CzPA, and PCzPA, and anthracene derivatives such as t-BuDNA, DNA, and DPAnth may be used. A high molecular compound such as poly (N-vinylcarbazole) (abbreviation: PVK) or poly (4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.
Note that other than these substances, any substance that has a property of transporting more holes than electrons may be used. Note that the layer containing a substance having a high hole-transport property is not limited to a single layer, and two or more layers containing the above substances may be stacked.

(Guest material for light emitting layer)
The light-emitting layer is a layer including a substance having high light-emitting properties, and various materials can be used. For example, as the substance having high light-emitting property, a fluorescent compound that emits fluorescence or a phosphorescent compound that emits phosphorescence can be used. A fluorescent compound is a compound that can emit light from a singlet excited state, and a phosphorescent compound is a compound that can emit light from a triplet excited state.
As a blue fluorescent material that can be used for the light emitting layer, pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, and the like can be used. Specifically, N, N′-bis [4- (9H-carbazol-9-yl) phenyl] -N, N′-diphenylstilbene-4,4′-diamine (abbreviation: YGA2S), 4- (9H -Carbazol-9-yl) -4 '-(10-phenyl-9-anthryl) triphenylamine (abbreviation: YGAPA), 4- (10-phenyl-9-anthryl) -4'-(9-phenyl-9H -Carbazol-3-yl) triphenylamine (abbreviation: PCBAPA) and the like.
An aromatic amine derivative or the like can be used as a green fluorescent material that can be used for the light emitting layer. Specifically, N- (9,10-diphenyl-2-anthryl) -N, 9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), N- [9,10-bis (1,1 '-Biphenyl-2-yl) -2-anthryl] -N, 9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N- (9,10-diphenyl-2-anthryl) -N, N ', N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N- [9,10-bis (1,1'-biphenyl-2-yl) -2-anthryl] -N, N' , N′-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), N- [9,10-bis (1,1′-biphenyl-2-yl)]-N- [4- (9H-carbazole) -9-yl) phenyl ] -N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N, N, 9-triphenylanthracen-9-amine (abbreviation: DPhAPhA), and the like.

Tetracene derivatives, diamine derivatives and the like can be used as red fluorescent materials that can be used for the light emitting layer. Specifically, N, N, N ′, N′-tetrakis (4-methylphenyl) tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N, N, N ′, And N′-tetrakis (4-methylphenyl) acenaphtho [1,2-a] fluoranthene-3,10-diamine (abbreviation: p-mPhAFD).

As a blue phosphorescent material that can be used for the light emitting layer, a metal complex such as an iridium complex, an osmium complex, or a platinum complex is used. Specifically, bis [2- (4 ′, 6′-difluorophenyl) pyridinato-N, C2 ′] iridium (III) tetrakis (1-pyrazolyl) borate (abbreviation: FIr6), bis [2- (4 ′ , 6′-difluorophenyl) pyridinato-N, C2 ′] iridium (III) picolinate (abbreviation: FIrpic), bis [2- (3 ′, 5′bistrifluoromethylphenyl) pyridinato-N, C2 ′] iridium (III ) Picolinate (abbreviation: Ir (CF3ppy) 2 (pic)), bis [2- (4 ′, 6′-difluorophenyl) pyridinato-N, C2 ′] iridium (III) acetylacetonate (abbreviation: FIracac), etc. Can be mentioned.
An iridium complex or the like is used as a green phosphorescent material that can be used for the light emitting layer. Tris (2-phenylpyridinato-N, C2 ′) iridium (III) (abbreviation: Ir (ppy) 3), bis (2-phenylpyridinato-N, C2 ′) iridium (III) acetylacetonate ( Abbreviations: Ir (ppy) 2 (acac)), bis (1,2-diphenyl-1H-benzimidazolato) iridium (III) acetylacetonate (abbreviation: Ir (pbi) 2 (acac)), bis (benzo [ h] quinolinato) iridium (III) acetylacetonate (abbreviation: Ir (bzq) 2 (acac)) and the like.
As a red phosphorescent material that can be used for the light emitting layer, a metal complex such as an iridium complex, a platinum complex, a terbium complex, or a europium complex is used. Specifically, bis [2- (2′-benzo [4,5-α] thienyl) pyridinato-N, C3 ′] iridium (III) acetylacetonate (abbreviation: Ir (btp) 2 (acac)), Bis (1-phenylisoquinolinato-N, C2 ′) iridium (III) acetylacetonate (abbreviation: Ir (piq) 2 (acac)), (acetylacetonato) bis [2,3-bis (4-fluoro Phenyl) quinoxalinato] iridium (III) (abbreviation: Ir (Fdpq) 2 (acac)), 2,3,7,8,12,13,17,18-octaethyl-21H, 23H-porphyrin platinum (II) (abbreviation) : PtOEP) and the like.
In addition, tris (acetylacetonato) (monophenanthroline) terbium (III) (abbreviation: Tb (acac) 3 (Phen)), tris (1,3-diphenyl-1,3-propanedionate) (monophenanthroline) europium (III) (abbreviation: Eu (DBM) 3 (Phen)), tris [1- (2-thenoyl) -3,3,3-trifluoroacetonato] (monophenanthroline) europium (III) (abbreviation: Eu ( A rare earth metal complex such as TTA) 3 (Phen)) emits light from a rare earth metal ion (electron transition between different multiplicity), and thus can be used as a phosphorescent compound.
Among these phosphorescent materials, ortho-metalated complexes of iridium (Ir), osmium (Os), or platinum (Pt) metal are preferable.

(Host material for light emitting layer)
The light-emitting layer may have a structure in which the above-described highly light-emitting substance (guest material) is dispersed in another substance (host material). Various materials can be used as a material for dispersing a highly luminescent substance. The lowest unoccupied orbital level (LUMO level) is higher than that of a highly luminescent substance, and the highest occupied orbital level ( It is preferable to use a substance having a low HOMO level.
As a substance (host material) for dispersing a substance having a high light-emitting property, the compound of the present invention is preferable. In addition to the compounds of the present invention, for example, 1) metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes, 2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives, 3) carbazole derivatives , Condensed aromatic compounds such as anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives, and 3) aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives. More specifically, tris (8-quinolinolato) aluminum (III) (abbreviation: Alq), tris (4-methyl-8-quinolinolato) aluminum (III) (abbreviation: Almq3), bis (10-hydroxybenzo [h Quinolinato) beryllium (II) (abbreviation: BeBq2), bis (2-methyl-8-quinolinolato) (4-phenylphenolato) aluminum (III) (abbreviation: BAlq), bis (8-quinolinolato) zinc (II) (Abbreviation: Znq), bis [2- (2-benzoxazolyl) phenolato] zinc (II) (abbreviation: ZnPBO), bis [2- (2-benzothiazolyl) phenolato] zinc (II) (abbreviation: ZnBTZ) Metal complexes such as 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (abbreviation: PB) ), 1,3-bis [5- (p-tert-butylphenyl) -1,3,4-oxadiazol-2-yl] benzene (abbreviation: OXD-7), 3- (4-biphenylyl)- 4-phenyl-5- (4-tert-butylphenyl) -1,2,4-triazole (abbreviation: TAZ), 2,2 ′, 2 ″-(1,3,5-benzenetriyl) tris ( Heterocyclic compounds such as 1-phenyl-1H-benzimidazole (abbreviation: TPBI), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), and 9- [4- (10-phenyl-9-anthryl) Phenyl] -9H-carbazole (abbreviation: CzPA), 3,6-diphenyl-9- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazole (abbreviation: DPCzPA) 9,10-bis (3,5-diphenylphenyl) anthracene (abbreviation: DPPA), 9,10-di (2-naphthyl) anthracene (abbreviation: DNA), 2-tert-butyl-9,10-di (2 -Naphthyl) anthracene (abbreviation: t-BuDNA), 9,9'-bianthryl (abbreviation: BANT), 9,9 '-(stilbene-3,3'-diyl) diphenanthrene (abbreviation: DPNS), 9,9 '-(Stilbene-4,4'-diyl) diphenanthrene (abbreviation: DPNS2), 3,3', 3 ''-(benzene-1,3,5-triyl) tripyrene (abbreviation: TPB3), 9,10 -Condensed aromatic compounds such as diphenylanthracene (abbreviation: DPAnth), 6,12-dimethoxy-5,11-diphenylchrysene, N, N-diphenyl-9- [4- (10-pheny -9-anthryl) phenyl] -9H-carbazol-3-amine (abbreviation: CzA1PA), 4- (10-phenyl-9-anthryl) triphenylamine (abbreviation: DPhPA), N, 9-diphenyl-N- [ 4- (10-phenyl-9-anthryl) phenyl] -9H-carbazol-3-amine (abbreviation: PCAPA), N, 9-diphenyl-N- {4- [4- (10-phenyl-9-anthryl) Phenyl] phenyl} -9H-carbazol-3-amine (abbreviation: PCAPBA), N- (9,10-diphenyl-2-anthryl) -N, 9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA) , Aromatic amine compounds such as NPB (or α-NPD), TPD, DFLDPBi, and BSPB can be used. In addition, a plurality of substances (host materials) for dispersing a substance having high luminescence (guest material) can be used.

(Electronic transport band)
The electron transport zone includes a substance having a high electron injection property and / or a high electron transport property. As described above, the electron transport zone preferably contains the compound of the present invention.
In the electron transport zone, lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF ₂ ), which are highly electron-injecting substances, are used. ), An alkali metal such as lithium oxide (LiOx), an alkaline earth metal, or a compound thereof. In addition, a substance in which an alkali metal, an alkaline earth metal, or a compound thereof is contained in a substance having an electron transporting property, specifically, a substance in which magnesium (Mg) is contained in Alq may be used. In this case, electron injection from the cathode can be performed more efficiently.
Alternatively, a composite material obtained by mixing an organic compound and an electron donating dopant may be used in the electron transport zone. Such a composite material is excellent in electron injecting property and electron transporting property because electrons are generated in the organic compound by the electron donating dopant. In this case, the organic compound is preferably a material that is excellent in transporting the generated electrons. Specifically, the compound of the present invention and the substance constituting the above-described electron transport layer (metal complex or heteroaromatic) Compounds). The electron donating dopant may be any substance that exhibits an electron donating property with respect to the organic compound. Specific examples include alkali metals, alkali metal compounds, alkaline earth metals, alkaline earth metal compounds, rare earth metals, and rare earth metal compounds. Examples of the alkali metal, alkaline earth metal, and rare earth metal include lithium, cesium, magnesium, calcium, erbium, and ytterbium. Alkali metal oxides and alkaline earth metal oxides are also preferable. For example, lithium oxide, calcium oxide, barium oxide, and the like can be used. A Lewis base such as magnesium oxide can also be used. Alternatively, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can be used.

In addition, the electron transport zone includes substances having high electron transport properties, such as 1) organometallic complexes such as aluminum complexes, beryllium complexes, and zinc complexes, 2) imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, Heteroaromatic compounds such as phenanthroline derivatives, and 3) polymer compounds can be used.
As the organometallic complex, it is preferable to use at least one selected from an organometallic complex containing an alkali metal, an organometallic complex containing an alkaline earth metal, and an organometallic complex containing a rare earth metal.
Specific examples of organometallic complexes include 8-quinolinolatolithium (abbreviation: Liq), Alq, tris (4-methyl-8-quinolinolato) aluminum (abbreviation: Almq3), bis (10-hydroxybenzo [h] quinolinato. ) Beryllium (abbreviation: BeBq ₂ ), BAlq, Znq, ZnPBO, ZnBTZ, or the like can be used.
Specific examples of the heteroaromatic compound include 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis [ 5- (pt-butylphenyl) -1,3,4-oxadiazol-2-yl] benzene (abbreviation: OXD-7), 3- (4-tert-butylphenyl) -4-phenyl-5- ( 4-biphenylyl) -1,2,4-triazole (abbreviation: TAZ), 3- (4-tert-butylphenyl) -4- (4-ethylphenyl) -5- (4-biphenylyl) -1,2, 4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), 4,4′-bis (5-methylbenzoxazol-2-yl) stilbene (Abbreviation: BzOs).
As specific examples of the high molecular compound, poly [(9,9-dihexylfluorene-2,7-diyl) -co- (pyridine-3,5-diyl)] (abbreviation: PF-Py), poly [ (9,9-dioctylfluorene-2,7-diyl) -co- (2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy) and the like.
The substances described here are mainly substances having an electron mobility of 10 ⁻⁶ cm ² / Vs or higher. Note that any substance other than the above substances may be used for the electron-transport layer as long as the substance has a higher electron-transport property than the hole-transport property. Further, the electron transport zone is not limited to a single layer, and two or more layers made of the above substances may be stacked.
In one embodiment of the present invention, the electron transport zone preferably further contains at least one selected from the electron donating dopant and the organometallic complex in addition to the compound of the present invention.

(cathode)
It is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a low work function (specifically, 3.8 eV or less) for the cathode. Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table of elements, that is, alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth such as magnesium (Mg). And other rare earth metals such as alloys and alloys containing them (for example, MgAg, AlLi) and alloys containing these.

(Acceptor layer)
In one embodiment of the organic EL device of the present invention, a layer containing an acceptor material, that is, an acceptor layer may be provided between the anode and the hole transport zone, and it is preferable to be so. This is expected to reduce drive voltage and manufacturing costs.
As the acceptor material, a compound represented by the following formula (K) is preferable.

[In the formula (K), R ⁴⁰¹ to R ⁴⁰⁶ are each independently a cyano group, —CONH ₂ , a carboxyl group, or —COOR ⁴⁰⁷ (R ⁴⁰⁷ is an alkyl group having 1 to 20 carbon atoms.) Or R ⁴⁰¹ and R ⁴⁰² , R ⁴⁰³ and R ⁴⁰⁴ , or R ⁴⁰⁵ and R ⁴⁰⁶ are bonded to each other to represent a group represented by —CO—O—CO—. ]
^Examples of the alkyl group for R ⁴⁰⁷ include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a cyclopentyl group, and a cyclohexyl group.
The thickness of the layer containing the acceptor material is not particularly limited, but is preferably 5 to 20 nm.

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

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

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

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

The organic EL device obtained by using the compound of the present invention has high luminous efficiency and can be driven at a low voltage. For this reason, it can be used for display devices such as organic EL panel modules; display devices such as televisions, mobile phones, and personal computers;

Next, the present invention will be described in more detail with reference to examples and comparative examples, but the present invention is not limited to the description of these examples.

Synthesis Example 1 (Synthesis of Compound (1))

Under an argon atmosphere, 3-bromo-7,12-diphenylbenzo [k] fluoranthene (3.00 g, 6.21 mmol) was dissolved in tetrahydrofuran (50 mL) and cooled to -78 ° C. Thereafter, n-BuLi (2.50 M hexane solution, 4.22 mL, 10.6 mmol) was added dropwise over 20 minutes, and the mixture was stirred at −78 ° C. for 1 hour. Then, the temperature was raised to −50 ° C., diphenylphosphine chloride (1.37 g, 6.21 mmol) was added, the temperature was raised to room temperature (25 ° C.), and the mixture was stirred for 8 hours.
Thereafter, methanol (30 mL) was added to the mixture to stop the reaction, the solvent was distilled off under reduced pressure, the residue was dissolved in dichloromethane (50 mL), hydrogen peroxide solution (10 mL) was added, and the mixture was stirred again for 8 hours. . Subsequently, the mixture was washed with brine, dried over magnesium sulfate, and concentrated. Thereafter, the mixture was purified by silica gel column chromatography to obtain a compound (1.12 g, 1.85 mmol, yield 30%).
As a result of mass spectrometry, the compound was m / e = 604, and was identified as the compound (1) (molecular weight 604.20).

Synthesis Example 2 (Synthesis of Compound (2))

Under an argon atmosphere, 7- (4-bromophenyl) -12-phenylbenzo [k] fluoranthene (3.00 g, 6.21 mmol) was dissolved in tetrahydrofuran (50 mL) and cooled to -78 ° C. Thereafter, n-BuLi (2.50 M hexane solution, 4.22 mL, 10.6 mmol) was added dropwise over 20 minutes, and the mixture was stirred at −78 ° C. for 1 hour. Then, the temperature was raised to −50 ° C., diphenylphosphine chloride (1.37 g, 6.21 mmol) was added, the temperature was raised to room temperature (25 ° C.), and the mixture was stirred for 8 hours.
Thereafter, methanol (30 mL) was added to the mixture to stop the reaction, the solvent was distilled off under reduced pressure, the residue was dissolved in dichloromethane (50 mL), hydrogen peroxide solution (10 mL) was added, and the mixture was stirred again for 8 hours. . Subsequently, the mixture was washed with brine, dried over magnesium sulfate, and concentrated. Thereafter, the mixture was purified by silica gel column chromatography to obtain a compound (1.31 g, 2.17 mmol, yield 35%).
As a result of mass spectrometry, the compound was m / e = 604, and was identified as the compound (2) (molecular weight 604.20).

Synthesis Example 3 (Synthesis of Compound (3))

(3-1) Synthesis of Intermediate (A1) In an argon atmosphere, 5-bromoacenaphthenequinone (10.0 g, 38.3 mmol) was dissolved in heated glacial acetic acid (500 mL), and phenylenediamine (5.38 g, 49.8 mmol) was added, followed by stirring at reflux temperature for 1 hour.
After completion of the reaction, the reaction solution was cooled and the precipitate was filtered off. Then, it recrystallized using the liquid mixture of a dimethylformamide and water, and the said intermediate body (A1) (8.93g, 26.8mmol, 70% of yield) was obtained.

(3-2) Synthesis of Intermediate (A2) Intermediate (A1) (8.50 g, 25.5 mmol) and tetrahydrofuran (300 mL) were mixed and cooled to −78 ° C. under an argon atmosphere. Thereafter, n-BuLi (1.60 M hexane solution, 16.7 mL, 26.8 mmol) was added, and the temperature was raised to 0 ° C. over 2 hours. Next, the mixture was cooled again to −78 ° C., trimethoxyborane (6.62 g, 63.8 mmol) was added, and the mixture was stirred at −78 ° C. for 10 minutes, and then heated to room temperature (25 ° C.) over 5 hours. .
After completion of the reaction, an aqueous hydrochloric acid solution (1M, 75 mL) was added to the reaction solution, and the mixture was stirred at room temperature (25 ° C.) for 1 hour and extracted with ethyl acetate. Then, magnesium sulfate was added to the extract and dried, followed by concentration, suspension washing with hexane, and filtration and recovery to obtain the intermediate (A2) (3.27 g, 11.0 mmol, yield 43%). Obtained.

(3-3) Synthesis of Compound (3) Under an argon atmosphere, intermediate (A2) (3.10 g, 10.4 mmol), (4-bromophenyl) phosphine oxide (3.71 g, 10.4 mmol), tris ( Dibenzylideneacetone) dipalladium (0) (143 mg, 0.156 mmol), triphenylphosphine (328 mg, 1.25 mmol), and tripotassium phosphate (13.2 g, 62.4 mmol) were mixed with 1, 4-dioxane (125 mL) was added, and the mixture was stirred at 100 ° C. for 8 hr.
After completion of the reaction, the reaction solution was diluted with water and extracted with chloroform. The extract was washed with saturated brine, dried by adding magnesium sulfate, concentrated, purified by silica gel column chromatography, recrystallized using ethyl acetate, and compound (3.86 g, 7.28 mmol, yield 70%) was obtained.
As a result of mass spectrometry, the compound was m / e = 530 and was identified as the compound (3) (molecular weight 530.15).

Synthesis Example 4 (Synthesis of Compound (4))

(4-1) Synthesis of Intermediate (B1) Acetic acid was added to acenaphthenequinone (12.2 g, 67.2 mmol) and 4-bromo-1,2-phenylenediamine (13.8 g, 73.9 mmol) under an argon atmosphere. (500 mL) was added and stirred at reflux temperature for 2 hours.
After cooling to room temperature (25 ° C.), water was added to the reaction solution, and the precipitated solid was separated by filtration and washed with water and methanol. The obtained solid was dissolved in toluene, activated carbon was added, and the mixture was stirred for 30 minutes and then filtered off. Toluene was distilled off under reduced pressure, and the precipitated solid was washed again with methanol, and after drying, the above intermediate (B1) (9.18 g, 27.6 mmol, yield 41%) was obtained.

(4-2) Synthesis of Compound (4) Under an argon atmosphere, intermediate (B1) (6.60 g, 19.8 mmol), (4- (4,4,5,5-tetramethyl-1,3,2) -Dioxaboran-2-yl) phenyl) diphenylphosphine oxide (8.81 g, 21.8 mmol), tetrakis (triphenylphosphine) palladium (0) (687 mg, 0.594 mmol), and aqueous sodium carbonate (2M, 29.7 mL) , 59.4 mmol) were added 1,2-dimethoxyethane (100 mL) and toluene (150 mL), and the mixture was stirred at 80 ° C. for 14 hours.
After cooling to room temperature (25 ° C.), water and toluene were added to the reaction solution, the organic layer was separated, washed with saturated brine, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography, and then recrystallized by adding 1,4-dioxane to obtain a compound (3.39 g, 6.39 mmol, yield 32%).
As a result of mass spectrometry, the compound was m / e = 530 and was identified as the compound (4) (molecular weight 530.57).

Synthesis Example 5 (Synthesis of Compound (5))

(5-1) Synthesis of Intermediate (C1) Acetic acid (366 mL) was added to acenaphthenequinone (6.67 g, 36.6 mmol) and 2,3-diaminophenol (5.00 g, 40.3 mmol) under an argon atmosphere. The mixture was further stirred at reflux temperature for 6 hours.
After cooling to room temperature (25 ° C.), water was added to the reaction solution, and the precipitated solid was separated by filtration and washed with water and methanol. The obtained solid was dissolved in dichloromethane and purified by silica gel short column chromatography. After purification, the product was washed with methanol again and dried, and the intermediate (C1) (3.18 g, 11.8 mmol, yield 32%) was obtained.

(5-2) Synthesis of Intermediate (C2) Pyridine (64 mL) was added to Intermediate (C1) (3.13 g, 11.6 mmol) under an argon atmosphere and mixed at 70 ° C. Then, after cooling to 0 ° C., trifluoromethanesulfonic anhydride (4.90 g, 17.4 mmol) was added dropwise over 5 minutes and stirred at 0 ° C. for 4 hours.
After completion of the reaction, water was added to the reaction solution, and the precipitated solid was separated by filtration and washed with water and methanol. The obtained solid was washed with acetone for 1 hour, and after drying, the intermediate (C2) (2.35 g, 5.84 mmol, yield 50%) was obtained.

(5-3) Synthesis of Compound (5) Under an argon atmosphere, intermediate (C2) (2.22 g, 5.52 mmol), (4- (4,4,5,5-tetramethyl-1,3,2) -Dioxaboran-2-yl) phenyl) diphenylphosphine oxide (4.89 g, 6.62 mmol), tetrakis (triphenylphosphine) palladium (0) (191 mg, 0.166 mmol), and aqueous sodium carbonate (2M, 8.27 mL) , 16.5 mmol) was added 1,2-dimethoxyethane (55 mL) and stirred at 80 ° C. for 2 hours.
After cooling to room temperature (25 ° C.), water and toluene were added to the reaction solution, the organic layer was separated, washed with saturated brine, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography and then recrystallized by adding toluene to obtain a compound (1.13 g, 2.13 mmol, yield 39%).
As a result of mass spectrometry, the compound was m / e = 530 and was identified as the compound (5) (molecular weight 530.57).

In addition, it is possible to synthesize the specified compound in the scope of claims by using the above-mentioned synthesis reaction and using a known alternative reaction or raw material suitable for the object.

[Production of organic EL element and evaluation of light emission performance]
Below, the structure of the compound used for preparation of the organic EL element of an Example and a comparative example is shown.

Moreover, the following performance of the produced organic EL element was measured by the following method.
(1) Drive voltage The drive voltage (V) when energized between the anode (ITO transparent electrode) and the metal cathode (metal Al) of the produced organic EL element so that the current density is 10 mA / cm ² Measured.
(2) Luminous efficiency An electric current was passed between the anode (ITO transparent electrode) and the metal cathode (metal Al) of the produced organic EL device so that the current density was 10 mA / cm ^2, and a spectral radiance meter (Konica Minolta) Luminous efficiency (cd / A) was measured using a product name “CS-1000” manufactured by the company.
(3) Life (LT97)
A DC continuous energization test was performed with the initial current density set to 50 mA / cm ² , and the time [LT97] (hr) until the luminance decreased to 97% with respect to the luminance at the start of the test was measured.

Example 1
A glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anode) of 25 mm × 75 mm × thickness 1.1 mm was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 30 minutes.
The glass substrate with the transparent electrode line after the cleaning is mounted on the substrate holder of the vacuum deposition apparatus, and the compound HI-1 is first deposited so as to cover the transparent electrode on the surface where the transparent electrode line is formed. An acceptor layer having a thickness of 5 nm was formed.
The compound HT-1 is vapor-deposited as a first hole transport material on the formed acceptor layer to form a first hole transport layer (hole transport zone) having a film thickness of 155 nm. The compound HT-2 was vapor-deposited on the layer to form a second hole transport layer (hole transport zone) having a thickness of 10 nm.
Further, the compound PGH-1 as a host compound and the compound PGD-1 as a phosphorescent dopant material are co-deposited on the second hole transport layer (PGH-1: PGD-1 = 95: 5). (Mass%)), a light emitting layer having a thickness of 40 nm was formed. The concentration of the compound PGD-1 in the light emitting layer was 5.0% by mass.
Subsequently to the formation of the light emitting layer, the compound (1) obtained in Synthesis Example 1 and 8-quinolinolatolithium (Liq) were co-evaporated (compound (1): Liq = 50: 50 ( Mass%)), and an electron transport layer (electron transport zone) having a film thickness of 36 nm was formed.
On this electron transport layer, 8-quinolinolato lithium (Liq) was vapor-deposited to form an electron injection layer having a thickness of 1 nm. Metal Al was vapor-deposited on this electron injection layer, and a metal cathode was formed with a film thickness of 80 nm to produce an organic EL device.

Example 2
An organic EL device was produced in the same manner as in Example 1 except that the compound (2) obtained in Synthesis Example 2 was used in place of the compound (1).

Comparative Example 1
An organic EL device was produced in the same manner as in Example 1 except that the comparative example compound was used instead of the compound (1).

For the organic EL devices obtained in Examples 1 and 2 and Comparative Example 1, the results of driving voltage (V) and luminous efficiency (cd / A) at a current density of 10 mA / cm ² measured by the above method are shown in Table 1. Shown in

From Table 1, the organic EL element produced in Examples 1 and 2 is superior in terms of light emission efficiency and can be driven at a lower voltage than the organic EL element produced in Comparative Example 1. became.
Since the compound of the present invention has a condensed fluoranthene structure, it is considered that the compound has higher electron affinity, and is considered to function advantageously for electron injection from the cathode. Therefore, in the organic EL device using the compound of the present invention, electrons are suitably supplied to the light emitting layer, so that it is considered that the carrier balance is optimized and the effect of improving the light emission efficiency is exhibited.

Example 3
A glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anode) of 25 mm × 75 mm × thickness 1.1 mm was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 30 minutes.
The glass substrate with the transparent electrode line after the cleaning is mounted on the substrate holder of the vacuum deposition apparatus, and the compound HI-1 is first deposited so as to cover the transparent electrode on the surface where the transparent electrode line is formed. An acceptor layer having a thickness of 5 nm was formed.
The compound HT-3 is deposited as a first hole transport material on the formed acceptor layer to form a first hole transport layer (hole transport zone) having a thickness of 80 nm, and the first hole transport layer is formed. The compound HT-4 was vapor-deposited on the layer to form a second hole transport layer (hole transport zone) having a thickness of 10 nm.
Further, the compound BH-1 as a host compound and the compound BD-1 as a fluorescent dopant material are co-deposited on the second hole transport layer (BH-1: BD-1 = 96: 4). (Mass%)), a light emitting layer having a thickness of 25 nm was formed. The concentration of the compound BD-1 in the light emitting layer was 4.0% by mass.
Subsequently to the formation of the light emitting layer, the compound (4) obtained in Synthesis Example 4 and 8-quinolinolatolithium (Liq) were co-evaporated (compound (4): Liq = 50: 50 ( Mass%)), and an electron transport layer (electron transport zone) having a film thickness of 25 nm was formed.
On this electron transport layer, 8-quinolinolato lithium (Liq) was vapor-deposited to form an electron injection layer having a thickness of 1 nm. Metal Al was vapor-deposited on this electron injection layer, and a metal cathode was formed with a film thickness of 80 nm to produce an organic EL device.

Example 4
An organic EL device was produced in the same manner as in Example 3 except that the compound (5) obtained in Synthesis Example 5 was used in place of the compound (4).

Comparative Example 2
An organic EL device was produced in the same manner as in Example 3 except that the comparative compound was used instead of the compound (4).

The organic EL devices fabricated in Examples 3 and 4 and Comparative Example 2, the driving voltage and current density measured by the above method is in 10mA / cm ² (V), and the initial current density life at 50 mA / cm ² [LT97] The results of (hr) are shown in Table 2.

From Table 2, the organic EL device produced in Examples 3 and 4 was superior in terms of life compared to the organic EL device produced in Comparative Example 2.

DESCRIPTION OF SYMBOLS 1 Organic electroluminescent element 3 Anode 4 Cathode 5 Light emitting layer 6 Hole transport zone (hole transport layer)
7 Electron transport zone (electron transport layer)
10 Organic thin film layer

Claims

A compound represented by the following general formula (1).

[In the formula (1), X 1 to X 10 each represent C (R A1 ) to C (R A10 ) or a nitrogen atom.
However, at least two selected from R A1 to R A10 are bonded to each other to form a saturated or unsaturated ring.
R A1 to R A10 each independently represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted group Heteroaryl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted arylthio group, substituted or unsubstituted silyl group, substituted or unsubstituted An amino group or a group represented by the following general formula (2).
However, at least one of R A1 to R A10 (including a group bonded to a carbon atom constituting the ring at a position where each ring is bonded to each other) is represented by the following general formula (2) It is group represented by these.

(In Formula (2), Z shows an oxygen atom, a sulfur atom, or a selenium atom.
L 1 is a single bond, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms, or a bond of 2 to 4 of these groups Is a divalent group.
Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, and Ar 1 And Ar 2 may be bonded to each other to form a ring. )]
In the formula (1), X 1 and X 2 , X 2 and X 3 , X 3 and X 4 , X 4 and X 5 , X 5 and X 6 , X 6 and X 7 , X 7 and X 8 , X 8 And at least one set selected from X 9 , X 9 and X 10 , and X 10 and X 1 are both groups selected from C (R A1 ) to C (R A10 ), and from R A1 to R A10 The compound according to claim 1, wherein two selected groups are bonded to each other to form any of the rings represented by the following general formulas (3-a) to (3-e).

[In the formulas (3-a) to (3-e), * represents a bonding part to a carbon atom, and Y represents —C (R B29 ) (R B30 ) —, —N (R B31 ) —, —Si (R B32 ) (R B33 ) —, —O—, or —S— is shown.
R B1 to R B33 each independently represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted group Heteroaryl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted arylthio group, substituted or unsubstituted silyl group, substituted or unsubstituted An amino group or a group represented by the general formula (2).
However, at least one of R A1 to R A10 and R B1 to R B28 in the formula (1) is a group represented by the general formula (2) according to claim 1. ]
The compound according to claim 1 or 2, represented by any one of the following general formulas (1-1) to (1-9):

[In the formulas (1-1) to (1-9), X 1 to X 10 each represent C (R A1 ) to C (R A10 ) or a nitrogen atom, and R A1 to R A10 represent It is the same as the description of.
Y represents —C (R B29 ) (R B30 ) —, —N (R B31 ) —, —Si (R B32 ) (R B33 ) —, —O—, or —S—.
R B1 to R B33 and R B1 ′ to R B4 ′ are each independently a hydrogen atom, halogen atom, cyano group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted Aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted arylthio group, substituted or unsubstituted A silyl group, a substituted or unsubstituted amino group, or a group represented by the general formula (2).
However, at least one of R A1 to R A10 , R B1 to R B28 , and R B1 ′ to R B4 ′ is a group represented by the general formula (2) according to claim 1. ]
The compound according to any one of claims 1 to 3, wherein X 1 to X 10 are each C (R A1 ) to C (R A10 ).
The compound according to any one of claims 1 to 4, which is represented by any one of the following general formulas (1-1A) to (1-9A).

[In the formulas (1-1A) to (1-9A), R A1 to R A10 are the same as described in claim 1, and Y represents —C (R B29 ) (R B30 ) —, —N ( R B31 ) —, —Si (R B32 ) (R B33 ) —, —O—, or —S— is shown. R B1 to R B33 and R B1 ′ to R B4 ′ are each independently a hydrogen atom, halogen atom, cyano group, substituted or unsubstituted alkyl group, substituted or unsubstituted cycloalkyl group, substituted or unsubstituted Aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted arylthio group, substituted or unsubstituted A silyl group, a substituted or unsubstituted amino group, or a group represented by the general formula (2).
However, at least one of R A1 to R A10 , R B1 to R B28 , and R B1 ′ to R B4 ′ is a group represented by the general formula (2) according to claim 1. ]
The compound according to claim 5, which is represented by the general formula (1-1A).
The compound according to any one of claims 1 to 3, wherein at least one of X 1 to X 10 is a nitrogen atom.
The compound according to any one of claims 1 to 3 and 7, which is represented by any one of the following general formulas (1-1B) to (1-8B).

[In the formulas (1-1B) to (1-8B), R A1 to R A10 are the same as described in claim 1, and Y represents —C (R B29 ) (R B30 ) —, —N ( R B31 ) —, —Si (R B32 ) (R B33 ) —, —O—, or —S— is shown. R B1 to R B4 , R B1 ′ to R B4 ′ , R B17 to R B20 , and R B29 to R B33 each independently represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group, Unsubstituted cycloalkyl group, substituted or unsubstituted aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted Alternatively, it is an unsubstituted arylthio group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amino group, or a group represented by the general formula (2).
However, at least one of R A1 to R A10 , R B1 to R B4 , R B1 ′ to R B4 ′ , and R B17 to R B20 is represented by the general formula (2) according to claim 1. It is a group. ]
The compound according to claim 8, which is represented by the general formula (1-1B).
The compound according to any one of claims 1 to 9, which has only one group represented by the general formula (2).
The compound according to claim 10, which is represented by any one of the following general formulas (1-1A-i) to (1-1A-iii):

[In the formulas (1-1A-i) to (1-1A-iii), L 1 , Ar 1 , Ar 2 , and Z are the same as described in claim 1.
R a1 , R a4 to R a10 and R b1 to R b4 each independently represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, substituted or unsubstituted Substituted aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted arylthio group, substituted or unsubstituted A substituted silyl group or a substituted or unsubstituted amino group.
However, any one of R a1 , R a4 to R a10 and R b1 to R b4 in the above formulas (1-1A-i) to (1-1A-iii) is any one of the above general formulas ( It is not a group represented by 2). ]
The compound according to claim 10, which is represented by any one of the following general formulas (1-1B-i) to (1-1B-iii):

[In the formulas (1-1Bi) to (1-1B-iii), L 1 , Ar 1 , Ar 2 , and Z are the same as described in claim 1.
R a5 to R a10 and R b1 to R b4 each independently represent a hydrogen atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted aryl. Group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group, substituted or unsubstituted alkylthio group, substituted or unsubstituted arylthio group, substituted or unsubstituted silyl Or a substituted or unsubstituted amino group.
However, R a5 to R a10 and R b1 to R b4 in the above formulas (1-1Bi) to (1-1B-iii) are all represented by the general formula (2) according to claim 1. It is not a represented group. ]
The compound according to claim 12, which is represented by the general formula (1-1B-i) or (1-1B-ii).
The compound according to claim 12, which is represented by the general formula (1-1B-i) or (1-1B-iii).
The compound according to any one of claims 1 to 14, wherein each of Ar 1 and Ar 2 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
The compound according to any one of claims 1 to 15, wherein each of Ar 1 and Ar 2 is a substituted or unsubstituted aryl group having 6 to 14 ring carbon atoms.
The L 1 is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms. Compound described in 1.
The compound according to any one of claims 1 to 16, wherein L 1 is a single bond.
The compound according to any one of claims 1 to 18, wherein Z is an oxygen atom.
R A1 to R A10 each independently represents a hydrogen atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms. Substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms, substituted or unsubstituted heteroaryl groups having 5 to 30 ring atoms, substituted or unsubstituted An unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, —Si (R C1 ) (R C2 ) (R C3 ), a group represented by —N (R D1 ) (R D2 ) (R C1 to R C3 and R D1 to R D2 are each independently , A hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms Or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, or a group represented by the following general formula (2).
R B1 to R B33 each independently represent a hydrogen atom, a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms. Substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms, substituted or unsubstituted heteroaryl groups having 5 to 30 ring atoms, substituted or unsubstituted An unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylthio group having 1 to 20 carbon atoms, a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms, —Si (R C1 ) (R C2 ) (R C3 ), a group represented by —N (R D1 ) (R D2 ) (R C1 to R C3 and R D1 to R D2 are each independently , A hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms Or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, or a group represented by the general formula (2).
An organic electroluminescent element material comprising the compound according to any one of claims 1 to 21.
An organic thin film layer composed of one or more layers including at least a light emitting layer is provided between an anode and a cathode facing each other, and at least one of the organic thin film layers is according to any one of claims 1 to 21. An organic electroluminescence device containing a compound.
The organic electroluminescence device according to claim 23, wherein the organic electroluminescence device has an electron transport zone between the light emitting layer and the cathode, and the electron transport zone contains the compound according to any one of claims 1 to 18. .
An electronic device equipped with the organic electroluminescence element according to claim 23 or 24.