WO2018164265A1

WO2018164265A1 - Compound, organic electroluminescent element material, organic electroluminescent element, and electronic device

Info

Publication number: WO2018164265A1
Application number: PCT/JP2018/009247
Authority: WO
Inventors: 匡羽毛田; 裕勝伊藤; 裕工藤
Original assignee: 出光興産株式会社
Priority date: 2017-03-10
Filing date: 2018-03-09
Publication date: 2018-09-13
Also published as: JP2020097525A

Abstract

A compound represented by formula (1) provides an organic electroluminescent element that exhibits exceptional luminous efficiency. (In formula (1), R1-R8, R11-R18, R21, R22, L1, L2, L3, Ar1, and Ar2 are as defined in the description.)

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 element containing the compound, an organic electroluminescence element using the compound, and an electronic device including the organic electroluminescence element.

Generally, an organic electroluminescence element (organic EL element) is composed of an anode, a cathode, and an organic layer 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. Therefore, the development of a compound that efficiently transports electrons or holes to the light emitting region and facilitates recombination of electrons and holes is important in obtaining a high-efficiency organic EL device.

Patent Document 1 discloses an amine compound in which a spirobifluorene structure is bonded to a central nitrogen atom directly or via an aromatic ring. Patent Document 1 describes that this compound is suitable as a hole transport material in a hole transport layer or an exciton blocking layer or as a matrix material in a light emitting layer.

Patent Document 2 discloses an amine compound in which a 9,9-disubstituted fluorene structure such as a 9,9-diphenylfluorene structure or a 9,9-dimethylfluorene structure is bonded to a central nitrogen atom directly or via an aromatic ring. ing. Patent Document 2 describes that this compound is suitable as a hole transport material and / or a hole injection material in a hole transport layer or an exciton blocking layer, or as a matrix material in a light emitting layer.

International Publication No. 2012/234627 International Publication No. 2014/015935

Conventionally, many compounds useful for the production of organic EL devices have been reported, but there is still a demand for compounds that further improve the characteristics of organic EL devices.

The present invention has been made to solve the above-described problems, and an object of the present invention is to provide an organic EL element exhibiting excellent luminous efficiency and a novel compound that realizes such an organic EL element.

As a result of intensive studies to achieve the above object, the present inventors realize an organic EL device in which a compound represented by the following formula (1) having a spiroanthracenefluorene skeleton exhibits excellent luminous efficiency. I found.

That is, in one aspect, the present invention provides a compound represented by formula (1) (hereinafter sometimes referred to as compound (1)).

(Where
R ¹ to R ⁸ and R ¹¹ to R ¹⁸ are each independently a hydrogen atom or a substituent, two adjacent groups selected from R ¹ to R ^4, two adjacent groups selected from R ⁵ to R ⁸ , Two adjacent groups selected from R ¹¹ to R ¹⁴ and two adjacent groups selected from R ¹⁵ to R ¹⁸ may be bonded to each other to form a ring structure.
However, ^one selected from R ¹ to R ⁸ and R ¹¹ to R ¹⁸ represents a single bond bonded to *, or the ring-forming atom of the ring structure is bonded to *.
R ²¹ and R ²² are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring. It is a heteroaryl group having 5 to 30 atoms.
L ¹ , L ² , and L ³ are each independently a single bond, 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. It is.
Ar ¹ and Ar ² are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted oxygen-containing heteroaryl group having 5 to 30 ring atoms, or substituted or unsubstituted. A sulfur-containing heteroaryl group having 5 to 30 ring atoms.
The substituent represented by R ¹ to R ⁸ and R ¹¹ to R ¹⁸ is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, substituted or unsubstituted Unsubstituted aryl group having 6 to 30 ring carbon atoms, substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, substituted or unsubstituted aralkyl group having 7 to 36 carbon atoms, substituted or unsubstituted An alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and a substituted or unsubstituted ring carbon number 6 A mono-, di- or tri-substituted silyl group having a substituent selected from aryl groups of 1 to 30; a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted carbon number Haloalkoxy groups to 30, a halogen atom, a cyano group, or a nitro group. )

In another aspect, the present invention provides a material for an organic electroluminescence device comprising the compound (1).

In yet another aspect, the present invention is an organic electroluminescent device comprising a cathode, an anode, and an organic layer disposed between the cathode and the anode, the organic layer comprising a light-emitting layer, Provided is an organic electroluminescence device in which at least one layer contains a compound (1).

In yet another aspect, the present invention provides an electronic device comprising the organic electroluminescence element.

Compound (1) realizes an organic EL device with further improved luminous efficiency.

It is the schematic which shows the structure of the organic EL element which concerns on 1 aspect of this invention.

In this specification, “carbon number XX to YY” of “substituted or unsubstituted ZZ group having XX to YY” represents the carbon number of unsubstituted ZZ group and does not include the carbon number of the substituent.

In this specification, “atom number XX to YY” of “substituted or unsubstituted ZZ group having XX to YY” represents the number of atoms of the unsubstituted ZZ group and does not include the number of atoms of the substituent.

In the present specification, the “unsubstituted ZZ group” of the “substituted or unsubstituted ZZ group” means that the hydrogen atom of the ZZ group is not substituted with a substituent.

In this 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 “ring-forming carbon number” refers to a carbon that forms the ring itself of a compound 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 atoms. When the ring has a substituent, the carbon atom contained in the substituent is not included in the ring-forming carbon atom. The same applies to the “ring carbon number” described below unless otherwise specified. For example, a benzene ring has 6 ring carbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridine ring has 5 ring carbon atoms, and a furan ring has 4 ring carbon atoms. For example, when the benzene ring or naphthalene ring has an alkyl substituent, the carbon atom of the alkyl substituent is not included in the ring-forming carbon atom. In the case of a fluorene-substituted fluorene ring (including a spirobifluorene ring), the carbon atom of the fluorene substituent is not included in the ring-forming carbon atom.

In the present specification, the “number of ring-forming atoms” refers to an atom that forms the ring itself of a compound in which atoms are bonded in a ring, for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, or a heterocyclic compound. Represents the number of An atom that does not form a ring, for example, a hydrogen atom bonded to an atom forming a ring and an atom included in a substituent bonded to an atom forming a ring are not included in the ring forming atom. The same applies to the “number of ring-forming atoms” described below unless otherwise specified. For example, the pyridine ring has 6 ring atoms, the quinazoline ring has 10 ring atoms, and the furan ring has 5 ring atoms. Hydrogen atoms and substituent atoms bonded to ring-forming carbon atoms of the pyridine ring or quinazoline ring are not included in the ring-forming atoms. In the case of a fluorene-substituted fluorene ring (including a spirobifluorene ring), the atom of the fluorene substituent is not included in the ring-forming atom.

The compound (compound (1)) according to one embodiment of the present invention is represented by the formula (1).

In the formula (1), one selected from R ¹ to R ⁸ and R ¹¹ to R ¹⁸ represents a single bond bonded to *. Further, two adjacent members selected from R ¹ to R ^4, two adjacent members selected from R ⁵ to R ^8, two adjacent members selected from R ¹¹ to R ¹⁴ , and R ¹⁵ to R ^{18 are} selected. Two adjacent groups may be bonded to each other to form a ring structure, and a ring-forming atom of the ring structure may be bonded to *.

Therefore, the compound (1) includes a compound represented by any one of the formulas (2) to (13).

(In the formula, ^one selected from R ¹ to R ⁵ , R ⁸ and R ¹¹ to R ¹⁸ represents a single bond bonded to *, or the ring-forming atom of ring structure A is bonded to *.)

(In the formula, ^{one selected} from R ¹ to R ⁴ , R ⁷ , R ⁸ , and R ¹¹ to R ¹⁸ represents a single bond bonded to *, or the ring-forming atom of ring structure B is bonded to * To do.)

(In the formula, ^one selected from R ¹ , R ⁴ , R ⁵ , R ⁸ , and R ¹¹ to R ¹⁸ represents a single bond bonded to *, or the ring-forming atom of the ring structure A or C is * To join.)

(In the formula, ^one selected from R ¹ to R ⁸ , R ¹¹ to R ¹⁵ and R ¹⁸ represents a single bond bonded to *, or a ring-forming atom of ring structure D is bonded to *.)

Hereinafter, details of each symbol of the equations (1) to (13) will be described.

R ¹ to R ⁸ and R ¹¹ to R ¹⁸ which do not represent a single bond bonded to * and do not form the ring structure are each independently a hydrogen atom or a substituent.
The substituent is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms; a substituted or unsubstituted carbon group having 3 to 30 ring carbon atoms, preferably 3 to 10 carbon atoms; More preferably 3 to 8, more preferably 5 or 6 cycloalkyl group; substituted or unsubstituted aryl group having 6 to 30, preferably 6 to 25, more preferably 6 to 18 ring carbon atoms; Substituted heteroaryl group having 5 to 30, preferably 5 to 24, more preferably 5 to 13 ring-forming atoms; substituted or unsubstituted 7 to 36, preferably 7 to 26, more preferably 7 to 20 carbon atoms A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms; a substituted or unsubstituted carbon group having 6 to 30 ring carbon atoms, preferably Is an aryloxy group having 6 to 25, more preferably 6 to 18; a substituted or unsubstituted alkyl group having 1 to 30, preferably 1 to 18, more preferably 1 to 8 carbon atoms, and a substituted or unsubstituted ring. A mono-, di- or tri-substituted silyl group having a substituent selected from aryl groups having 6 to 30 carbon atoms, preferably 6 to 25 carbon atoms, more preferably 6 to 18 carbon atoms; substituted or unsubstituted 1 to 30 carbon atoms, preferably 1-18, more preferably 1-8 haloalkyl group; substituted or unsubstituted haloalkoxy group having 1-30, preferably 1-18, more preferably 1-8 carbon atoms; halogen atom; cyano group; or nitro group It is.

In the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, the alkyl group is, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group (including isomer group), hexyl group (including isomer group), heptyl group (including isomer group), octyl group (including isomer group), nonyl group (isomer) Group), decyl group (including isomer group), undecyl group (including isomer group), or dodecyl group (including isomer group); methyl group, ethyl group, n-propyl group, isopropyl Group, n-butyl group, isobutyl group, s-butyl group, t-butyl group and pentyl group (including isomer group) are preferred; methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group Group, isobu Group, more preferably a s- butyl group, and a t- butyl group; a methyl group and t- butyl group more preferred.

In the substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, the cycloalkyl group is, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, or a cycloheptyl group, A cyclohexyl group is preferred.

In the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, the aryl group is, for example, a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, an acenaphthylenyl group, a biphenylenyl group, a fluorenyl group, or an s-indacenyl group. , As-indacenyl group, anthryl group, benzoanthryl group, aceantrilenyl group, phenanthryl group, benzophenanthryl group, phenalenyl group, naphthacenyl group, fluoranthenyl group, pyrenyl group, chrysenyl group, benzochrysenyl group, triphenylenyl group , A pentacenyl group, a picenyl group, or a pentaphenyl group; preferably a phenyl group, a biphenylyl group, a terphenylyl group, or a naphthyl group; more preferably a phenyl group, a biphenylyl group, or a naphthyl group; Properly is a phenyl group.
As the substituted aryl group, for example, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, and a 9,9′-spirobifluorenyl group are preferable.

In the substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, the heteroaryl group contains 1 to 5, preferably 1 to 3, more preferably 1 to 2 ring-forming heteroatoms. . The ring-forming heteroatom is selected from, for example, a nitrogen atom, a sulfur atom and an oxygen atom. The free valence of the heteroaryl group may be present on the ring-forming carbon atom or, if structurally possible, on the ring-forming nitrogen atom.
The heteroaryl group is, for example, pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group, furyl group, thienyl group, oxazolyl group, isoxazolyl group, oxadiazolyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, pyridyl group, pyridazinyl group, Pyrimidinyl group, pyrazinyl group, triazinyl group, indolyl group, isoindolyl group, indolizinyl group, quinolidinyl group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, benzoimidazolyl group, indazolyl group, phenanthrolinyl group Phenanthridinyl group, acridinyl group, phenazinyl group, carbazolyl group, benzocarbazolyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group, dibenzothiol Nyl group, naphthobenzofuranyl group, benzothiophenyl group (benzothienyl group, the same applies hereinafter), dibenzothiophenyl group (dibenzothienyl group, the same applies hereinafter), or naphthobenzothiophenyl group (naphthobenzothienyl group, the same applies hereinafter) Preferably, furyl, thienyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, naphthobenzofuranyl, dibenzothiophenyl Naphthobenzothiophenyl group, carbazolyl group, or benzocarbazolyl group; more preferably, thienyl group, benzothiophenyl group, dibenzofuranyl group, naphthobenzofuranyl group, dibenzothiophenyl group, naphthobenzothiol Phenyl group, carbazolyl Or benzo carbazolyl group.
Examples of the substituted heteroaryl group include 9-phenylcarbazolyl group, 9-biphenylylcarbazolyl group, 9-phenylphenylcarbazolyl group, 9-naphthylcarbazolyl group, and diphenylcarbazol-9-yl. Group, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group (phenyldibenzothienyl group) are preferred.

In the substituted or unsubstituted aralkyl group having 7 to 36 carbon atoms, the aryl moiety of the aralkyl group is selected from the above aryl groups having 6 to 30, preferably 6 to 25, more preferably 6 to 18 ring carbon atoms. The alkyl moiety corresponds to a group selected from the above substituted or unsubstituted alkyl groups having 1 to 30, preferably 1 to 18, more preferably 1 to 8 carbon atoms. As the aralkyl group, a benzyl group, a phenethyl group, and a phenylpropyl group are preferable, and a benzyl group is more preferable.

In the substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, the alkyl portion of the alkoxy group is the above substituted or unsubstituted alkyl group having 1 to 30, preferably 1 to 18, more preferably 1 to 8 carbon atoms. Selected from. As the alkoxy group, a t-butoxy group, a propoxy group, an ethoxy group, and a methoxy group are preferable, an ethoxy group and a methoxy group are more preferable, and a methoxy group is further preferable.

In the substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, the aryl moiety of the aryloxy group has the above substituted or unsubstituted ring carbon number of 6 to 30, preferably 6 to 25, more preferably. Selected from 6-18 aryl groups. As the aryloxy group, a terphenyloxy group, a biphenyloxy group, and a phenoxy group are preferable, a biphenyloxy group and a phenoxy group are more preferable, and a phenoxy group is more preferable.

The mono-, di- or tri-substituted silyl group has a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, preferably 1 to 18, more preferably 1 to 8 carbon atoms, and the above substituted or unsubstituted group. Are selected from aryl groups having 6 to 30, preferably 6 to 25, more preferably 6 to 18 ring carbon atoms. Tri-substituted silyl groups are preferred, for example, trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, propyldimethylsilyl group, isopropyldimethylsilyl group, triphenylsilyl group, phenyldimethylsilyl group, t-butyldiphenylsilyl group, And tolylylsilyl group.

In the substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms, the haloalkyl group is at least one, preferably 1 to 1, of the above alkyl groups having 1 to 30, preferably 1 to 18, more preferably 1 to 8 carbon atoms. The group obtained by substituting seven hydrogen atoms or all the hydrogen atoms with halogen atoms is mentioned. The halogen atom is selected from a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, preferably a fluorine atom.
The haloalkyl group is preferably a fluoroalkyl group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms, including a heptafluoropropyl group (including an isomer group), a pentafluoroethyl group, 2,2, A 2-trifluoroethyl group and a trifluoromethyl group are more preferable, a pentafluoroethyl group, a 2,2,2-trifluoroethyl group, and a trifluoromethyl group are more preferable, and a trifluoromethyl group is particularly preferable.

In the substituted or unsubstituted haloalkoxy group, the haloalkyl portion of the haloalkoxy group is selected from the above haloalkyl groups having 1 to 30, preferably 1 to 18, and more preferably 1 to 8 carbon atoms. The haloalkoxy group is preferably a fluoroalkoxy group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms, including a heptafluoropropoxy group (including isomer groups), a pentafluoroethoxy group, and 2,2. 1,2-trifluoroethoxy group and trifluoromethoxy group are more preferable, pentafluoroethoxy group, 2,2,2-trifluoroethoxy group and trifluoromethoxy group are more preferable, and trifluoromethoxy group is particularly preferable.

The halogen atom is a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, and a fluorine atom is preferred.

R ¹ to R ⁷ and R ¹¹ to R ¹⁸ which do not represent the single bond bonded to * and do not form the ring structure are preferably a hydrogen atom, a substituted or unsubstituted alkyl having 1 to 30 carbon atoms, respectively. Group, substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted Or an unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, a halogen atom, or a cyano group; more preferably a hydrogen atom, substituted or An unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted hetero atom having 5 to 30 ring atoms; Group, a halogen atom, or a cyano group.

In one embodiment of the present invention, R ¹ to R ⁷ and R ¹¹ to R ¹⁸ that do not represent a single bond bonded to * and do not form the ring structure may be all hydrogen atoms.
In another embodiment of the present invention, one selected from R ¹ to R ⁷ and R ¹¹ to R ¹⁸ may be a single bond bonded to *, and all the remaining may be hydrogen atoms.

Two adjacent members selected from R ¹ to R ⁴ , preferably R ² and R ³ or R ³ and R ⁴ ; two adjacent members selected from R ⁵ to R ⁸ , preferably R ⁵ and R ⁶ or R ⁶ And R ⁷ ; two adjacent members selected from R ¹¹ to R ¹⁴ , preferably two adjacent members selected from R ¹² and R ¹³ ; and R ¹⁵ to R ¹⁸ , preferably R ¹⁶ and R ¹⁷ are bonded to each other. To form a ring structure.
In one embodiment of the present invention, all of the two adjacent groups may not form a ring structure.

Examples of the ring structure include substituted or unsubstituted aromatic hydrocarbon rings having 6 to 18 ring carbon atoms, substituted or unsubstituted aliphatic hydrocarbon rings having 5 to 18 ring carbon atoms, substituted or unsubstituted rings. And an aromatic heterocyclic ring having 5 to 18 ring atoms and a substituted or unsubstituted aliphatic heterocyclic ring having 5 to 18 ring atoms. The ring structure may be a condensed ring.

Examples of the aromatic hydrocarbon ring having 6 to 18 ring carbon atoms include an aromatic hydrocarbon selected from benzene, biphenylene, naphthalene, anthracene, benzoanthracene, phenanthrene, benzophenanthrene, phenalene, pyrene, chrysene, and triphenylene. A ring is mentioned.

Examples of the aliphatic hydrocarbon ring having 5 to 18 ring carbon atoms include a cyclopentene ring, a cyclopentadiene ring, a cyclohexene ring, a cyclohexadiene ring, and the aromatic hydrocarbon ring having 6 to 18 ring carbon atoms. An aliphatic hydrocarbon ring obtained by partial hydrogenation can be mentioned.

Examples of the aromatic heterocyclic ring having 5 to 18 ring atoms include pyrrole, furan, thiophene, pyridine, imidazole, pyrazole, indole, isoindole, benzofuran, isobenzofuran, benzothiophene, benzimidazole, indazole, dibenzofuran, An aromatic heterocyclic ring selected from naphthobenzofuran, dibenzothiophene, naphthobenzothiophene, carbazole, and benzocarbazole is exemplified.

Examples of the aliphatic heterocyclic ring having 5 to 18 ring atoms include an aliphatic heterocyclic ring obtained by partially hydrogenating the aromatic heterocyclic ring having 5 to 18 ring atoms.

The ring structure is preferably a benzene ring.

In one embodiment of the present invention, one selected from R ¹ to R ⁸ and R ¹¹ to R ¹⁸ is preferably a single bond bonded to *, and is selected from R ² to R ⁷ , R ¹² , and R ^17. More preferably, one is a single bond bonded to *, more preferably one selected from R ² to R ⁷ is a single bond bonded to *, R ² , R ⁴ , R ⁵ , and R ⁷ It is particularly preferred that one selected from is a single bond bonded to *.

In another embodiment of the present invention, the aromatic hydrocarbon ring having 6 to 18 ring carbon atoms, the aliphatic hydrocarbon ring having 5 to 18 ring carbon atoms, the aromatic heterocycle having 5 to 18 ring atoms. The ring and the ring-forming atom of the aliphatic heterocyclic ring having 5 to 18 ring-forming atoms may be bonded to *.

R ²¹ and R ²² are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms, a substituted or unsubstituted carbon atom number 6 An aryl group having from ˜30, preferably from 6 to 25, more preferably from 6 to 18, or a substituted or unsubstituted heteroaryl group having from 5 to 30, preferably from 5 to 24, more preferably from 5 to 13 ring atoms. is there.
R ²¹ and R ²² are preferably not bonded to each other and therefore do not form a ring structure.

Details of the respective substituents represented by R ²¹ and R ²² are the corresponding substitutions described above with respect to R ¹ to R ⁷ and R ¹¹ to R ¹⁸ which do not represent a single bond bonded to * and do not form the ring structure. Each group is the same.

R ²¹ and R ²² are preferably a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, more preferably a methyl group, an ethyl group, n -Propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, phenyl group, biphenylyl group, or naphthyl group, more preferably a methyl group or a phenyl group.

L ¹ , L ² and L ³ are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 30, preferably 6 to 25, more preferably 6 to 18 ring carbon atoms, or a substituted or unsubstituted group. Substituted heteroarylene groups having 5 to 30, preferably 5 to 24, more preferably 5 to 13 ring-forming atoms.

In the substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms of L ¹ and L ² , the arylene group includes, for example, a phenylene group, a biphenylylene group, a terphenylylene group, a naphthylene group, an anthrylene group, a benzoanthrylene group, Phenanthrylene group, benzophenanthrylene group, phenalenylene group, picenylene group, pentaphenylene group, pyrenylene group, chrysenylene group, benzocrisenylene group, triphenylenylene group, fluoranthenylene group, or fluorenylene group; preferably phenylene A group, a biphenylylene group, a terphenylylene group, a naphthylene group, a phenanthrylene group, or a fluorenylene group; more preferably a group selected from the following formula:

More preferably, it is a group selected from the following formulas;

More preferably, an o-phenylene group, m-phenylene group, p-phenylene group, 4,4′-biphenylylene group, 4,3′-biphenylylene group, 4,2′-biphenylylene group, 1,4-naphthylene group, or 2,6-naphthylene group; more preferably p-phenylene group or 2,6-naphthylene group; particularly preferably p-phenylene group.
As the substituted arylene group, a 9,9-dimethylfluorenediyl group, a 9,9-diphenylfluorenediyl group, and a 9,9′-spirobifluorenediyl group are preferable.

In the substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms of L ¹ and L ² , the heteroarylene group has 1 to 5, preferably 1 to 3, more preferably 1 to 2 rings. Contains forming heteroatoms. The ring-forming heteroatom is selected from, for example, a nitrogen atom, a sulfur atom, and an oxygen atom. The free valence may be present on the ring-forming carbon atom or on the nitrogen atom where structurally possible.
Examples of the heteroarylene group include pyrrole, imidazole, pyrazole, triazole, furan, thiophene, oxazole, isoxazole, oxadiazole, thiazole, isothiazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, isodol Indole, indolizine, quinolidine, quinoline, isoquinoline, cinnoline, phthalazine, quinazoline, quinoxaline, benzimidazole, indazole, phenanthroline, phenanthridine, acridine, phenazine, carbazole, benzocarbazole, xanthene, benzofuran, isobenzofuran, dibenzofuran, naphthobenzofuran , Benzothiophene, dibenzothiophene, naphthobenzothiophene, benzox A divalent residue of an aromatic heterocyclic ring selected from azole, benzisoxazole, phenoxazine, benzothiazole, benzoisothiazole, and phenothiazine; preferably pyridine, pyrimidine, triazine, indole, quinoline, quinazoline, Divalent aromatic heterocycle selected from quinoxaline, benzimidazole, indazole, phenanthroline, phenanthridine, acridine, carbazole, benzocarbazole, benzofuran, dibenzofuran, naphthobenzofuran, benzothiophene, dibenzothiophene, naphthobenzothiophene, and benzoxazole And more preferably pyridine, pyrimidine, triazine, carbazole, benzocarbazole, benzofuran, dibenzofuran, naphthobenzof Emissions, a divalent residue of an aromatic heterocyclic ring selected from benzothiophene, and dibenzothiophene.
One of the two free valences of the arylene group or heteroarylene group of L ¹ and L ² is bonded to the central nitrogen atom, and the other is bonded to Ar ¹ or Ar ² .

L ¹ and L ² are each preferably a single bond or a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms. In one embodiment of the present invention, L ¹ and L ² are preferably a single bond. In another embodiment of the present invention, ^one of L ¹ and L ² is a single bond, and the other is a substituted or unsubstituted ring. An arylene group having 6 to 30 carbon atoms is preferable, and in another embodiment of the present invention, L ¹ and L ² are each preferably a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms. .

In the substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms of L ^3, the arylene group includes, for example, a phenylene group, a biphenylylene group, a terphenylylene group, a naphthylene group, an anthrylene group, a benzoanthrylene group, a phenanthrylene group, Benzophenanthrylene group, phenalenylene group, picenylene group, pentaphenylene group, pyrenylene group, chrysenylene group, benzocrisenylene group, triphenylenylene group, fluoranthenylene group, fluorenylene group, or 9,9'-spirobiflur An oleylene group; preferably a phenylene group, a biphenylylene group, a terphenylylene group, or a naphthylene group; more preferably a group selected from the following formulae;

More preferably, it is a group selected from the following formulas;

More preferred is an o-phenylene group, m-phenylene group, p-phenylene group, 4,4′-biphenylylene group, 4,3′-biphenylylene group, or 4,2′-biphenylylene group; more preferred is p- A phenylene group.
As the substituted arylene group, a 9,9-dimethylfluorenediyl group, a 9,9-diphenylfluorenediyl group, and a 9,9′-spirobifluorenediyl group are preferable.

In the substituted or unsubstituted heteroarylene group having 5 to 30 ring atoms of L ^3, the heteroarylene group has 1 to 5, preferably 1 to 3, more preferably 1 to 2 ring-forming heteroatoms. including. The ring-forming heteroatom is selected from, for example, a nitrogen atom, a sulfur atom, and an oxygen atom. The free valence may be present on the ring-forming carbon atom or on the nitrogen atom where structurally possible.
Examples of the heteroarylene group include pyrrole, imidazole, pyrazole, triazole, furan, thiophene, oxazole, isoxazole, oxadiazole, thiazole, isothiazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, indole, isodol Indole, indolizine, quinolidine, quinoline, isoquinoline, cinnoline, phthalazine, quinazoline, quinoxaline, benzimidazole, indazole, phenanthroline, phenanthridine, acridine, phenazine, carbazole, benzocarbazole, xanthene, benzofuran, isobenzofuran, dibenzofuran, naphthobenzofuran , Benzothiophene, dibenzothiophene, naphthobenzothiophene, benzox A divalent residue of an aromatic heterocyclic ring selected from azole, benzisoxazole, phenoxazine, benzothiazole, benzoisothiazole, and phenothiazine; preferably pyridine, pyrimidine, triazine, indole, quinoline, quinazoline, Divalent aromatic heterocycle selected from quinoxaline, benzimidazole, indazole, phenanthroline, phenanthridine, acridine, carbazole, benzocarbazole, benzofuran, dibenzofuran, naphthobenzofuran, benzothiophene, dibenzothiophene, naphthobenzothiophene, and benzoxazole And more preferably pyridine, pyrimidine, triazine, carbazole, benzocarbazole, benzofuran, dibenzofuran, naphthobenzof Emissions, a divalent residue of an aromatic heterocyclic ring selected from benzothiophene, and dibenzothiophene.
One of the two free valences of the arylene group or heteroarylene group of L ³ is bonded to the central nitrogen atom, and the other is bonded to the spiroanthracene fluorene skeleton.

L ³ is preferably a single bond or a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms. In one embodiment of the present invention, L ³ is preferably a single bond. In another embodiment of the present invention, L ³ is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, preferably a phenylene group. Preferably there is.

Ar ¹ and Ar ² are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, preferably 6 to 25, more preferably 6 to 18; substituted or unsubstituted ring atoms having 5 to An oxygen-containing heteroaryl group of 30, preferably 5 to 24, more preferably 5 to 13; or a sulfur containing 5-30, preferably 5-24, more preferably 5-13, substituted or unsubstituted ring-forming atoms A heteroaryl group;

In one embodiment of the present invention, Ar ¹ and Ar ² are preferably each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
In another embodiment of the present invention, Ar ¹ and Ar ² are preferably each independently a substituted or unsubstituted oxygen-containing heteroaryl group having 5 to 30 ring atoms.
In still another embodiment of the present invention, Ar ¹ and Ar ² are preferably each independently a substituted or unsubstituted sulfur-containing heteroaryl group having 5 to 30 ring atoms.
In still another embodiment of the present invention, ^one of Ar ¹ and Ar ² is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and the other is a substituted or unsubstituted ring atom having 5 to 30 ring atoms. It is preferably an oxygen-containing heteroaryl group.
In still another embodiment of the present invention, ^one of Ar ¹ and Ar ² is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and the other is a substituted or unsubstituted ring atom having 5 to 30 ring atoms. It is preferably a sulfur-containing heteroaryl group.
In still another embodiment of the present invention, ^one of Ar ¹ and Ar ² is a substituted or unsubstituted oxygen-containing heteroaryl group having 5 to 30 ring atoms, and the other is a substituted or unsubstituted ring atom having 5 rings. It is preferably a ˜30 sulfur-containing heteroaryl group.

In the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms of Ar ¹ and Ar ² , the aryl group is, for example, a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, an acenaphthylenyl group, a biphenylenyl group, a fluorenyl group. S-indacenyl group, as-indacenyl group, anthryl group, benzoanthryl group, aceantrirenyl group, phenanthryl group, benzophenanthryl group, phenalenyl group, naphthacenyl group, fluoranthenyl group, pyrenyl group, chrysenyl group, A benzocrisenyl group, a triphenylenyl group, a pentacenyl group, a picenyl group, or a pentaphenyl group; preferably a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, an s-indacenyl group, an as-indacenyl group, an anthryl group Group, benzoanthryl group, phenanthryl group, benzophenanthryl group, fluoranthenyl group, pyrenyl group, chrysenyl group, benzocrisenyl group, or triphenylenyl group; more preferably phenyl group, biphenylyl group, terphenylyl group, naphthyl group , A fluorenyl group, a phenanthryl group, or a triphenylenyl group; more preferably, a phenyl group, a p-biphenyl group, an m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, and a p-terphenyl-3. -Yl group, p-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, 2-phenanthryl group, 9-phenanthryl group, 2-triphenylenyl group, fluoren-2-yl group, or fluorene-4 -An yl group.
The substituted aryl group is preferably a 9,9′-spirobifluoren-2-yl group, a 9,9′-spirobifluoren-4-yl group, a 9,9-diphenylfluoren-2-yl group, -Diphenylfluoren-4-yl group, 9,9-dimethylfluoren-2-yl group, 9,9-dimethylfluoren-4-yl group, 10,10-dimethyl (anthracene-9,9'-fluorene) -2 It is a '-yl group or a 10,10-dimethyl (anthracene-9,9'-fluorene) -4'-yl group.

In the substituted or unsubstituted oxygen-containing heteroaryl group having 5 to 30 ring atoms of Ar ¹ and Ar ² , the oxygen-containing heteroaryl group is, for example, a furyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a xanthenyl group. Benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl group, benzoisoxazolyl group, or phenoxazinyl group; preferably furyl group, benzofuranyl group, dibenzofuran More preferably a dibenzofuranyl group or a naphthobenzofuranyl group; still more preferably a dibenzofuranyl group; particularly preferably a 1-dibenzofuranyl group, 2- Dibenzofuranyl group or 4-dibenzofuranyl group That.

In the substituted or unsubstituted sulfur-containing heteroaryl group having 5 to 30 ring atoms of Ar ¹ and Ar ² , the sulfur-containing heteroaryl group includes, for example, a thienyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a benzothio group A phenyl group, a dibenzothiophenyl group, a naphthobenzothiophenyl group, a benzothiazolyl group, a benzoisothiazolyl group, or a phenothiazinyl group; preferably a thienyl group, a benzothiophenyl group, a dibenzothiophenyl group, or a naphthobenzothiophenyl group More preferably a dibenzothiophenyl group or a naphthobenzothiophenyl group; still more preferably a dibenzothiophenyl group; particularly preferably a 1-dibenzothiophenyl group, a 2-dibenzothiophenyl group, or 4- Dibenzothiopheny A group.

In one embodiment of the present invention, L ¹ and L ² are each selected from a single bond, a phenylene group, a biphenylene group, a terphenylene group, and a naphthylene group, and Ar ¹ and Ar ² are each a phenyl group, a biphenylyl group, a naphthyl group, Fluorenyl group, phenanthryl group, triphenylenyl group, 9,9'-spirobifluorenyl group, 9,9-diphenylfluorenyl group, 9,9-dimethylfluorenyl group, and 10,10-dimethyl (anthracene- It is preferably selected from 9,9′-fluorenyl) yl groups.

In one embodiment of the present invention, it is preferable that —L ¹ —Ar ¹ and —L ² —Ar ² are each independently selected from the following groups.

In this specification, unless otherwise specified, an arbitrary substituent referred to as “substituted or unsubstituted” is a substituted or unsubstituted alkyl having 1 to 30, preferably 1 to 18, more preferably 1 to 8 carbon atoms. A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, preferably 3 to 10, more preferably 3 to 8, more preferably 5 or 6, a substituted or unsubstituted ring carbon number 6 to 6 30, preferably 6-25, more preferably 6-18 aryl groups; substituted or unsubstituted heteroaryl groups having 5-30, preferably 5-24, more preferably 5-13, ring atoms, preferably A substituted or unsubstituted oxygen-containing or sulfur-containing heteroaryl group having 5 to 30, preferably 5 to 24, more preferably 5 to 13 ring-forming atoms; substituted or unsubstituted carbon Aralkyl group having 7 to 36, preferably 7 to 26, more preferably 7 to 20; Substituted or unsubstituted alkoxy group having 1 to 30, preferably 1 to 18, more preferably 1 to 8 carbon atoms; A substituted or unsubstituted aryloxy group having 6 to 30, preferably 6 to 25, more preferably 6 to 18 carbon atoms; a substituted or unsubstituted carbon atom having 1 to 30, preferably 1 to 18, more preferably 1 to 8 A mono-, di- or tri-substituted silyl group having a substituent selected from an alkyl group and a substituted or unsubstituted aryl group having 6 to 30, preferably 6 to 25, more preferably 6 to 18 ring-forming carbon atoms; Unsubstituted C 1-30, preferably 1-18, more preferably 1-8 haloalkyl groups; substituted or unsubstituted C 1-30, preferably 1-18, more preferred Ku haloalkoxy group having 1 to 8; a halogen atom; selected from the group consisting of and a nitro group; a cyano group.
Details of the optional substituent are as described for the substituents of R ¹ to R ⁸ and R ¹¹ to R ¹⁸ that do not represent a single bond bonded to * and do not form the ring structure. Further, unless otherwise specified, adjacent arbitrary substituents may be bonded to form a ring.

The production method of compound (1) is not particularly limited, and those skilled in the art can easily produce the compound (1) by the method described in the following examples or by a method obtained by modifying the method with reference to a known synthesis method. Can do.

Specific examples of the compound (1) of the present invention are shown below, but are not limited thereto.

Organic EL Element Material The organic EL element material of the present invention contains compound (1). The content of the compound (1) in the organic EL device material of the present invention is not particularly limited, and may be, for example, 1% by mass or more (including 100%), and 10% by mass or more (including 100%). It is preferably 50% by mass or more (including 100%), more preferably 80% by mass or more (including 100%), and 90% by mass or more (including 100%). It is particularly preferred that The material for an organic EL device of the present invention is useful for producing an organic EL device.

Organic EL Element Next, the organic EL element of the present invention will be described.
An organic EL element has an organic layer between a cathode and an anode. The organic layer includes a light emitting layer, and at least one of the organic layers includes the compound (1).
As an example of the organic layer containing the compound (1), a hole transport zone (hole transport layer, hole injection layer, electron blocking layer, exciton blocking layer, etc.) provided between the anode and the light emitting layer, Examples include, but are not limited to, a light emitting layer, a space layer, and an electron transport zone (an electron transport layer, an electron injection layer, a hole blocking layer, etc.) provided between the cathode and the light emitting layer. The compound (1) is used as a material of a hole transport zone or a light emitting layer of a fluorescent or phosphorescent EL device, preferably a material of a hole transport zone, more preferably a material of a hole transport layer.

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

For example, typical element configurations of simple organic EL elements include the following element configurations.
(1) Anode / light emitting unit / cathode The above light emitting unit may be a laminated type having a plurality of phosphorescent light emitting layers and fluorescent light emitting layers. In that case, excitons generated in the phosphorescent light emitting layer diffuse into the fluorescent light emitting layer. A space layer for preventing this may be provided between the light emitting layers. A typical layer structure of the simple light emitting unit is shown below. The layers in parentheses are optional.
(A) (hole injection layer /) hole transport layer / fluorescent light emitting layer (/ electron transport layer / electron injection layer)
(B) (hole injection layer /) hole transport layer / phosphorescent layer (/ electron transport layer / electron injection layer)
(C) (hole injection layer /) hole transport layer / first fluorescent light emitting layer / second fluorescent light emitting layer (/ electron transport layer / electron injection layer)
(D) (hole injection layer /) hole transport layer / first phosphorescent light emitting layer / second phosphorescent light emitting layer (/ electron transport layer / electron injection layer)
(E) (hole injection layer /) hole transport layer / phosphorescent layer / space layer / fluorescent layer (/ electron transport layer / electron injection layer)
(F) (hole injection layer /) hole transport layer / first phosphorescent light emitting layer / second phosphorescent light emitting layer / space layer / fluorescent light emitting layer (/ electron transport layer / electron injection layer)
(G) (hole injection layer /) hole transport layer / first phosphorescent light emitting layer / space layer / second phosphorescent light emitting layer / space layer / fluorescent light emitting layer (/ electron transport layer / electron injection layer)
(H) (hole injection layer /) hole transport layer / phosphorescent layer / space layer / first fluorescent layer / second fluorescent layer (/ electron transport layer / electron injection layer)
(I) (hole injection layer /) hole transport layer / electron blocking layer / fluorescent light emitting layer (/ electron transport layer / electron injection layer)
(J) (hole injection layer /) hole transport layer / electron blocking layer / phosphorescent layer (/ electron transport layer / electron injection layer)
(K) (hole injection layer /) hole transport layer / exciton blocking layer / fluorescent light emitting layer (/ electron transport layer / electron injection layer)
(L) (hole injection layer /) hole transport layer / exciton blocking layer / phosphorescent layer (/ electron transport layer / electron injection layer)
(M) (hole injection layer /) first hole transport layer / second hole transport layer / fluorescent light emitting layer (/ electron transport layer / electron injection layer)
(N) (hole injection layer /) first hole transport layer / second hole transport layer / fluorescent light emitting layer (/ first electron transport layer / second electron transport layer / electron injection layer)
(O) (hole injection layer /) first hole transport layer / second hole transport layer / phosphorescent layer (/ electron transport layer / electron injection layer)
(P) (hole injection layer /) first hole transport layer / second hole transport layer / phosphorescent layer (/ first electron transport layer / second electron transport layer / electron injection layer)
(Q) (hole injection layer /) hole transport layer / fluorescent light emitting layer / hole blocking layer (/ electron transport layer / electron injection layer / electron injection layer)
(R) (hole injection layer /) hole transport layer / phosphorescent layer / hole blocking layer (/ electron transport layer / electron injection layer)
(S) (hole injection layer /) hole transport layer / fluorescent light emitting layer / triplet blocking layer (/ electron transport layer / electron injection layer)
(T) (hole injection layer /) hole transport layer / phosphorescent layer / triplet blocking layer (/ electron transport layer / electron injection layer)

The plurality of phosphorescent light emitting layers, and the phosphorescent light emitting layer and the fluorescent light emitting layer may be light emitting layers having different colors. For example, the light emitting unit (f) includes a 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) / electron transporting layer. There may be.
An electron blocking layer may be provided between each light emitting layer and the hole transport layer or space layer. A hole blocking layer may be provided between each light emitting layer and the electron transport layer. By providing the electron blocking layer or the hole blocking layer, electrons or holes can be confined in the light emitting layer, the charge recombination probability in the light emitting layer can be increased, and the light emission efficiency can be improved.

The following element structure can be mentioned as a typical element structure of a tandem type organic EL element.
(2) Anode / first light emitting unit / intermediate layer / second light emitting unit / cathode Here, for example, the first light emitting unit and the second light emitting unit can be independently selected from the above light emitting units.
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. It is a layer to supply and can be formed with a well-known material.

FIG. 1 shows a schematic configuration of an example of the organic EL element. The organic EL element 1 includes a substrate 2, an anode 3, a cathode 4, and a light emitting unit (organic layer) 10 disposed between the anode 3 and the cathode 4. The light emitting unit 10 has at least one light emitting layer 5. An anode side organic layer 6 (hole injection layer, hole transport layer, etc.) between the light emitting layer 5 and the anode 3, and a cathode side organic layer 7 (electron injection layer, electron transport) between the light emitting layer 5 and the cathode 4. Layer, etc.) may be formed. Further, an electron blocking layer (not shown) may be provided on the light emitting layer 5 on the anode 3 side, and a hole blocking layer (not shown) may be provided on the light emitting layer 5 on the cathode 4 side. Thereby, electrons and holes can be confined in the light emitting layer 5 and the exciton generation efficiency in the light emitting layer 5 can be further increased.

In the present invention, a host combined with a fluorescent dopant (fluorescent light emitting material) is called a fluorescent host, and a host combined with a phosphorescent dopant is called 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 for forming a phosphorescent light emitting layer containing a phosphorescent dopant, and does not mean that it cannot be used as a material for forming 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 material of the substrate, for example, glass, quartz, plastic, or the like can be used. Further, a flexible substrate may be used. Examples of the flexible substrate include a plastic substrate made of polycarbonate, polyarylate, polyether sulfone, polypropylene, polyester, polyvinyl fluoride, or polyvinyl chloride, and an inorganic vapor deposition film.

Anode A metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a high work function (for example, 4.0 eV or more) is preferably used for the anode formed on the substrate. Examples thereof include indium tin oxide (ITO); indium oxide-tin oxide containing silicon or silicon oxide; indium oxide-zinc oxide; indium oxide containing tungsten oxide and zinc oxide; graphene and the like . In addition, gold, platinum, nickel, tungsten, chromium, molybdenum, iron, cobalt, copper, palladium, titanium, nitrides of the metal (for example, titanium nitride), and the like can be given.

These anode materials are usually formed by sputtering. For example, indium oxide-zinc oxide is formed by sputtering a target in which 1 to 10 wt% of zinc oxide is added to indium oxide. Indium oxide containing tungsten oxide and zinc oxide is formed by sputtering a target containing 0.5 to 5 wt% tungsten oxide and 0.1 to 1 wt% zinc oxide with respect to indium oxide. The anode may be formed by other methods such as a vacuum deposition method, a coating method, an ink jet method, a spin coating method, and the like.

The hole injection layer formed in contact with the anode is formed using a material that facilitates hole injection regardless of the work function of the anode. Therefore, as the anode material, a general material such as a metal, an alloy, an electrically conductive compound, a mixture thereof, and an element belonging to Group 1 or Group 2 of the periodic table can be used.
Materials having a low work function, for example, alkali metals such as lithium and cesium, alkaline earth metals such as magnesium, calcium and strontium, alloys containing these metals (for example, MgAg and AlLi), rare earth metals such as europium and ytterbium, An alloy containing a rare earth metal can also be used as the anode material. When an anode is formed using an alkali metal, an alkaline earth metal, or an alloy containing these metals, a vacuum evaporation method or a sputtering method can be used. Furthermore, when using a silver paste etc., the apply | coating method, the inkjet method, etc. can be used.

Hole injection layer The hole injection layer is a layer containing a material having a high hole injection property (hole injection material).

Hole injection materials include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide Products, manganese oxides, and the like can be used.

Low molecular organic compounds such as 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 Phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis [N- (9-phenylcarbazol-3-yl) -N-phenylamino] -9-phenylcarbazole (abbreviation: PCzPCA2), 3- [N- (1 An aromatic amine compound such as -naphthyl) -N- (9-phenylcarbazol-3-yl) amino] -9-phenylcarbazole (abbreviation: PCzPCN1) can also be used as the hole injection layer material.

Polymer compounds (oligomers, dendrimers, polymers, etc.) such as 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: Poly-TPD) or the like can also be used as the hole injection layer material. 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.

Furthermore, it is also preferable to use an acceptor material such as a hexaazatriphenylene (HAT) compound represented by the following formula (K).

(Wherein R ₂₁ to R ₂₆ may be the same as or different from each other, and each independently represents a cyano group, —CONH ₂ , a carboxyl group, or —COOR ₂₇ (R ₂₇ represents an alkyl group having 1 to 20 carbon atoms or Represents a cycloalkyl group having a number of 3 to 20. However, R ₂₁ and R ₂₂ , R ₂₃ and R ₂₄ , or R ₂₅ and R ₂₆ are bonded to each other and represented by —CO—O—CO—. Group may be formed.)
Examples of R ₂₇ include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, a cyclopentyl group, and a cyclohexyl group.

Furthermore, a compound represented by the following formula (2-1) or (2-2) is also preferable as the hole injection layer material.

In formulas (2-1) and (2-2), Ar ²¹ represents a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms or a substituted or unsubstituted ring forming atom number of 5 to 30 atoms. Represents an aromatic heterocycle. The aromatic hydrocarbon ring is preferably a benzene ring. The aromatic heterocyclic ring is preferably a ring having 6 ring atoms, for example, a pyridine ring, a pyrazine ring, and a pyridazine ring.

In formulas (2-1) and (2-2), X ²³ to X ²⁸ are each independently C (R) or a nitrogen atom.
R is independently a hydrogen atom, a halogen atom, a hydroxyl group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, substituted Or a monosubstituted, disubstituted or trisubstituted silyl group having a substituent selected from an unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, substituted or unsubstituted An alkoxy group having an alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having an aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and a substituted group Or a mono- or di-substituted amino group having a substituent selected from an unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted carbon An alkylthio group having 1 to 30 alkyl groups, a substituted or unsubstituted arylthio group having an aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms. .
The details of the alkyl group, aryl group, and heteroaryl group are the same as the corresponding groups described with respect to an arbitrary substituent when “substituted or unsubstituted”.

In the formulas (2-1) and (2-2), a ²¹ to a ²³ are ring structures represented by the following formula (2b).

X ²⁰ in the formula (2b) is represented by any of the following formulas (2b-1) to (2b-12).

(In the formulas (2b-1) to (2b-12), R ²⁰ has the same meaning as R.)

In the formulas (2-1) and (2-2), R ²³ to R ²⁸ are each independently synonymous with R.

Specific examples of the compounds represented by formulas (2-1) and (2-2) are described below, but are not limited to the following compounds.

Hole Transport Layer The hole transport layer is a layer containing a material having a high hole transport property (hole transport material). The compound (1) of the present invention is preferably used for the hole transport layer alone or in combination with the following compounds.

As the hole transporting material other than the compound (1), for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives and the like can be used.

Examples of the aromatic amine compound include 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 '-Screw And [N- (spiro-9,9′-bifluoren-2-yl) -N-phenylamino] biphenyl (abbreviation: BSPB). The above compound has a hole mobility of 10 ⁻⁶ cm ² / Vs or higher.

Examples of the carbazole derivative include 4,4′-di (9-carbazolyl) biphenyl (abbreviation: CBP), 9- [4- (9-carbazolyl) phenyl] -10-phenylanthracene (abbreviation: CzPA), 9 And -phenyl-3- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazole (abbreviation: PCzPA).

Examples of the anthracene derivative include 2-t-butyl-9,10-di (2-naphthyl) anthracene (abbreviation: t-BuDNA), 9,10-di (2-naphthyl) anthracene (abbreviation: DNA), 9,10-diphenylanthracene (abbreviation: DPAnth) and the like can be given.

Polymer compounds such as poly (N-vinylcarbazole) (abbreviation: PVK) and poly (4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used for the hole transport layer.

As long as the compound has a higher hole transporting property than the electron transporting property, a compound other than the above may be used as the hole transporting layer material.

The hole transport layer may be a single layer or a laminate composed of two or more layers. For example, the hole transport layer may be a layer including a first hole transport layer (anode side) and a second hole transport layer (cathode side). In this case, the compound (1) may be contained in one of the first hole transport layer and the second hole transport layer, or may be contained in both, provided that the first hole transport layer includes The compound (1) contained is different from the compound (1) contained in the second hole transport layer. Each layer of the two or more hole transport layers may contain a hole transport material other than the above-described compound (1).
In one embodiment of the present invention, the compound (1) is preferably contained in only one of the first hole transport layer and the second hole transport layer, and in another embodiment, the compound (1) is contained in the first positive transport layer. It is preferable that it is contained only in the hole transport layer. In still another embodiment, it is preferable that the compound (1) is contained only in the second hole transport layer. In still another embodiment, the compound (1) is contained in the first hole transport layer. It is preferable to be included in both the first hole transport layer and the second hole transport layer.

Light-Emitting Layer Dopant Material The light-emitting layer is a layer containing a highly luminescent material (dopant material), and various materials such as a fluorescent light-emitting material and a phosphorescent material can be used as the dopant material. The fluorescent light-emitting material is a compound that emits light from a singlet excited state, and the phosphorescent material is a compound that emits light from a triplet excited state.

As a blue fluorescent material, 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. 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-Ile Phenyl] -N- phenyl-anthracene-2-amine (abbreviation: 2YGABPhA), N, N, 9- triphenylamine anthracene-9-amine (abbreviation: DPhAPhA), and the like.

Tetracene derivatives, diamine derivatives, etc. can be used as red fluorescent materials. 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).

A metal complex such as an iridium complex, an osmium complex, or a platinum complex is used as the blue phosphorescent material. 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. Is mentioned.

An iridium complex or the like is used as a green phosphorescent material. 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, 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 (acetylacetonate) (monophenanthroline) terbium (III) (abbreviation: Tb (acac) ₃ (Phen)), tris (1,3-diphenyl-1,3-propanedionato) (monophenanthroline) europium (III) (abbreviation: Eu (DBM) ₃ (Phen)), tris [1- (2-thenoyl) -3,3,3-trifluoroacetonato] (monophenanthroline) europium (III) (abbreviation: Eu ( Rare earth metal complexes such as TTA) ₃ (Phen)) can be used as phosphorescent materials because rare earth metal ions emit light (electron transition between different multiplicity).

Host Material for Light-Emitting Layer The dopant material described above may be dispersed in another material (host material). It is preferable to use a material having a lowest lowest orbital level (LUMO level) and a lower highest occupied orbital level (HOMO level) than the dopant material.

Examples of host materials include (1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes,
(2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, phenanthroline derivatives,
(3) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, chrysene derivatives,
(4) Aromatic amine compounds such as triarylamine derivatives and condensed polycyclic aromatic amine derivatives are used.

Examples of the metal complex include 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) and the like,
Examples of the heterocyclic compound include 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (abbreviation: PBD), 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 (1-phenyl-1H-benzimidazole) (Abbreviation: TPBI), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), etc.
Examples of the condensed aromatic compound include 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 ( Abbreviations: 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 ″-(benzene-1,3,5-triyl) tripyrene (abbreviation: TPB3), 9,10-diphenylanthracene (abbreviation: DPAnth), 6,12-dimethoxy-5,11-diphenylchrysene, etc. Are mentioned,
Examples of the aromatic amine compound include N, N-diphenyl-9- [4- (10-phenyl-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), 4,4′-bis [N- (1- Naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB or α-NPD), N, N′-bis (3-methylphenyl) -N, N′-diphenyl- [1,1′-biphenyl] -4, 4′-diamine (abbreviation: TPD), 4,4′-bis [N- (9,9-dimethylfluoren-2-yl) -N-phenylamino] biphenyl (abbreviation: DFLDPBi, 4,4′-bis [ And N- (spiro-9,9′-bifluoren-2-yl) -N-phenylamino] biphenyl (abbreviation: BSPB).
A plurality of host materials may be used.

Electron Transport Layer The electron transport layer is a layer containing a material having a high electron transport property (electron transport material). For the electron transport layer, for example,
(1) Metal complexes such as aluminum complexes, beryllium complexes, zinc complexes,
(2) aromatic heterocyclic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, phenanthroline derivatives,
(3) A polymer compound can be used.

Examples of the metal complex include tris (8-quinolinolato) aluminum (III) (abbreviation: Alq), tris (4-methyl-8-quinolinolato) aluminum (abbreviation: Almq3), bis (10-hydroxybenzo [h] quinolinato ) Beryllium (abbreviation: BeBq ₂ ), 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), and bis [2- (2-benzothiazolyl) phenolato] zinc (II) (abbreviation: ZnBTZ).

As the heteroaromatic compound, for example, 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) still Emissions (abbreviation: BzOs), and the like.

As the polymer compound, for example, 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).

The above material is a compound having an electron mobility of 10 ⁻⁶ cm ² / Vs or higher. Note that materials other than those described above may be used for the electron-transport layer as long as the material has a higher electron-transport property than the hole-transport property. Further, the electron transport layer is not limited to a single layer, and may be a stack of two or more layers each including the above material.

Electron Injection Layer The electron injection layer is a layer containing a material having a high electron injection property (electron injection material). For the electron injection layer, an alkali metal such as lithium, cesium, calcium, lithium fluoride, cesium fluoride, calcium fluoride, or lithium oxide, an alkaline earth metal, or a compound thereof can be used. In addition, an electron transporting compound containing an alkali metal, an alkaline earth metal, or a compound thereof, for example, an Alq containing magnesium may be used. In this case, electron injection from the cathode can be performed more efficiently.

Alternatively, a composite material containing an organic compound and an electron donor (donor) may be used for the electron injection layer. Since the organic compound receives electrons from the electron donor, such a composite material is excellent in electron injecting property and electron transporting property. The organic compound is preferably a compound that is excellent in transporting received electrons. For example, the above-described electron transport layer materials (metal complexes, aromatic heterocyclic compounds, and the like) can be used. The electron donor may be any compound that can donate electrons to the organic compound. For example, alkali metals, alkaline earth metals, and rare earth metals are preferable, and lithium, cesium, magnesium, calcium, erbium, ytterbium, and the like can be given. Alkali metal oxides and alkaline earth metal oxides are preferable, and lithium oxide, calcium oxide, barium oxide, and the like can be given. A Lewis base such as magnesium oxide can also be used. Alternatively, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can be used.

Cathode The cathode is preferably formed of a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a low work function (for example, 3.8 eV or less). Examples of such cathode materials include alkali metals such as lithium and cesium, alkaline earth metals such as magnesium, calcium, and strontium, alloys containing these metals (for example, MgAg, AlLi), europium (Eu), and ytterbium. Examples thereof include rare earth metals such as (Yb) and alloys containing rare earth metals.
When the cathode is formed using an alkali metal, an alkaline earth metal, or an alloy containing these metals, a vacuum evaporation method or a sputtering method can be used. Moreover, when using a silver paste, the apply | coating method, the inkjet method, etc. can be used.
By providing an electron injection layer, a cathode is formed using various conductive materials such as indium oxide-tin oxide containing Al, Ag, ITO, graphene, silicon, or silicon oxide regardless of the work function. Can do. These conductive materials can be formed by a sputtering method, an inkjet method, a spin coating method, or the like.

Insulating layer Since an organic EL element applies an electric field to an ultra-thin film, pixel defects are likely to occur due to leakage or short circuit. In order to prevent this, a thin film insulating layer may be inserted between the pair of electrodes.
Examples of the material used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, and silicon oxide. Germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide, and the like. A mixture of these materials may be used, or a laminate of a plurality of layers containing these materials may be used.

Space layer The space layer is, for example, in the case of laminating a fluorescent light emitting layer and a phosphorescent light emitting layer, for the purpose of adjusting the carrier balance so as not to diffuse excitons generated in the phosphorescent light emitting layer into the fluorescent light emitting layer. This is a layer provided between the fluorescent light emitting 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, the space layer is preferably formed of a material having both electron transport properties and hole transport properties. 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.

Blocking Layer A blocking layer such as an electron blocking layer, a hole blocking layer, or a triplet blocking layer may be provided in a portion adjacent to the light emitting layer. The electron blocking layer is a layer that prevents electrons from leaking from the light emitting layer to the hole transport layer, and the hole blocking layer is a layer that prevents holes from leaking from the light emitting layer to the electron transport layer. The triplet blocking layer has a function of preventing excitons generated in the light emitting layer from diffusing into an adjacent layer and confining the excitons in the light emitting layer.

Each layer of the organic EL element can be formed by a conventionally known vapor deposition method, coating method, or the like. For example, it can be formed by a known deposition method such as a vacuum deposition method or a molecular beam deposition method (MBE method), or a known coating method such as a dipping method, a spin coating method, a casting method, a bar coating method, or a roll coating method. it can.

The film thickness of each layer is not particularly limited, but in general, if the film thickness is too thin, defects such as pinholes are likely to occur. Conversely, if it is too thick, a high driving voltage is required and the efficiency deteriorates, so 5 nm to 10 μm is preferable. It is more preferably 0.2 μm.

The organic EL element can be used for display devices such as an organic EL panel module, display devices such as a television, a mobile phone, and a personal computer, and electronic equipment such as a light emitting device for lighting and a vehicle lamp.

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

Intermediate synthesis example 1: Intermediate A
Intermediate A was synthesized according to the following synthetic route.

(1) Synthesis of intermediate a1 (2- (2-bromophenyl) propan-2-ol)

Under an argon atmosphere, methyl 2-bromobenzoate (430 g) was dissolved in THF (tetrahydrofuran, 4.0 L), and a 1.0 mol / L THF solution (6.0 L) of methylmagnesium bromide was added dropwise at 0 ° C. The reaction mixture was warmed to room temperature, stirred for 16 hours, cooled again to 0 ° C., and 2M hydrochloric acid was added dropwise to neutralize. The resulting mixture was extracted with toluene. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and concentrated under reduced pressure to obtain intermediate a1 (400 g, yield 72%).

(2) Synthesis of intermediate a2 (1-bromo-2- (2-phenylpropan-2-yl) benzene)

Under an argon atmosphere, intermediate a1 (660 g) was dissolved in benzene (2.5 L), and hydrochloric acid gas was bubbled for 4 hours. Thereafter, Ar gas was bubbled for 1 hour and cooled to 0 ° C. Subsequently, aluminum chloride (81.8 g) was added to the reaction vessel, and the mixture was stirred at the same temperature for 30 minutes and then at room temperature for 16 hours. Water was added to the resulting mixture and extracted with toluene. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and then concentrated under reduced pressure to obtain intermediate a2 (749 g, yield 55%).

(3) Synthesis of intermediate a3

Under an argon atmosphere, a mixture of magnesium (17.8 g), THF (320 mL), 1,2-dibromoethane (0.6 mL) was stirred at 25 ° C. for 20 minutes, intermediate a2 (158 g) was added, and Grignard reagent was added. Adjusted. The Grignard reagent was added dropwise to a solution of 2-bromo-9-fluorenone (136 g) in THF (1.4 L), and the mixture was stirred at 60 ° C. for 30 minutes. The reaction mixture was extracted with toluene at room temperature, and the organic layer was washed with a saturated aqueous ammonium chloride solution and water. The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to obtain intermediate a3 (137 g, yield 52%).

(4) Synthesis of intermediate A

A mixture of intermediate a3 (146 g), acetic acid (1.2 L) and concentrated hydrochloric acid (292 mL) was stirred at 88 ° C. for 1 hour. The mixture was allowed to cool to room temperature and extracted with toluene. The product was purified by silica gel column chromatography and recrystallization to obtain Intermediate A (29 g, yield 20%). As a result of mass spectrum analysis, it was m / e = 436 with respect to the molecular weight 436 of the intermediate A.

Intermediate synthesis example 2: Intermediate B

Using 4-bromo-9-fluorenone (72 g) instead of 2-bromo-9-fluorenone and 78 g of intermediate a2, intermediate a4 was obtained in the same manner as in the synthesis of (3) intermediate a3 above ( 54 g, 42% yield). Intermediate A4 (20 g) was used instead of Intermediate a3, and Intermediate B was obtained in the same manner as in the synthesis of (4) Intermediate A above (1.54 g, yield 8%). As a result of mass spectrum analysis, it was m / e = 436 with respect to the molecular weight 436 of the intermediate B.

Synthesis Example 1: Synthesis of Compound 1

Under an argon atmosphere, known intermediate 1 (2.21 g), intermediate A (3.00 g), tris (dibenzylideneacetone) dipalladium (0) (126 mg), XPhos (262 mg), sodium-t-butoxide ( 1.98 g) and xylene (110 mL) were heated and stirred at 110 ° C. for 3 hours. After allowing to cool, the reaction mixture was filtered, and the filtrate was extracted with toluene and purified by column chromatography to obtain Compound 1 as a white solid (4.55 g, 98%).
As a result of mass spectrum analysis, it was m / e = 677 with respect to the molecular weight 677 of Compound 1.

Synthesis Example 2: Synthesis of Compound 2

In Synthesis Example 1, Compound 2 was synthesized in the same manner using Intermediate 2 instead of Intermediate 1.
As a result of mass spectrum analysis, it was m / e = 727 with respect to the molecular weight 727 of compound 2.

Synthesis Example 3: Synthesis of Compound 3

In Synthesis Example 1, Compound 3 was synthesized in the same manner using Intermediate 3 instead of Intermediate 1.
As a result of mass spectrum analysis, it was m / e = 651 with respect to the molecular weight 651 of compound 3.

Synthesis Example 4: Synthesis of Compound 4

In Synthesis Example 1, Compound 4 was synthesized in the same manner using Intermediate 4 instead of Intermediate 1.
As a result of mass spectrum analysis, it was m / e = 677 with respect to the molecular weight 677 of compound 4.

Synthesis Example 5: Synthesis of Compound 5

In Synthesis Example 1, Compound 5 was synthesized in the same manner using Intermediate 5 instead of Intermediate 1.
As a result of mass spectrum analysis, it was m / e = 677 with respect to the molecular weight 677 of compound 5.

Synthesis Example 6 Synthesis of Compound 6

In Synthesis Example 1, Compound 6 was synthesized in the same manner using Intermediate 6 instead of Intermediate 1.
As a result of mass spectrum analysis, it was m / e = 701 with respect to the molecular weight 701 of compound 6.

Synthesis Example 7 Synthesis of Compound 7

In Synthesis Example 1, Compound 7 was synthesized in the same manner using Intermediate 7 instead of Intermediate 1.
As a result of mass spectrum analysis, it was m / e = 717 with respect to the molecular weight 717 of compound 7.

Synthesis Example 8 Synthesis of Compound 8

In Synthesis Example 1, Compound 8 was synthesized in the same manner using Intermediate 8 instead of Intermediate 1.
As a result of mass spectrum analysis, it was m / e = 839 with respect to the molecular weight 839 of compound 8.

Synthesis Example 9 Synthesis of Compound 9

In Synthesis Example 1, Compound 9 was synthesized in the same manner using Intermediate 9 instead of Intermediate 1.
As a result of mass spectrum analysis, it was m / e = 841 with respect to the molecular weight 841 of Compound 9.

Synthesis Example 10 Synthesis of Compound 10

In Synthesis Example 1, Compound 10 was synthesized in the same manner using Intermediate 10 instead of Intermediate 1.
As a result of mass spectrum analysis, it was m / e = 839 with respect to the molecular weight 839 of compound 10.

Synthesis Example 11 Synthesis of Compound 11

In Synthesis Example 1, Compound 11 was synthesized in the same manner using Intermediate 11 instead of Intermediate 1.
As a result of mass spectrum analysis, it was m / e = 841 with respect to the molecular weight 841 of Compound 11.

Synthesis Example 12 Synthesis of Compound 12

In Synthesis Example 1, Compound 12 was synthesized in the same manner using Intermediate 12 instead of Intermediate 1.
As a result of mass spectrum analysis, it was m / e = 829 with respect to the molecular weight 829 of compound 12.

Synthesis Example 13 Synthesis of Compound 13

In Synthesis Example 1, Compound 13 was synthesized in the same manner using Intermediate 13 instead of Intermediate 1.
As a result of mass spectrum analysis, it was m / e = 767 with respect to the molecular weight 767 of compound 13.

Synthesis Example 14 Synthesis of Compound 14

In Synthesis Example 1, Compound 14 was synthesized in the same manner using Intermediate 14 instead of Intermediate 1.
As a result of mass spectrum analysis, it was m / e = 783 with respect to the molecular weight 783 of compound 14.

Synthesis Example 15: Synthesis of Compound 15

In Synthesis Example 1, Compound 15 was synthesized in the same manner using Intermediate 15 instead of Intermediate 1.
As a result of mass spectrum analysis, it was m / e = 767 with respect to the molecular weight 767 of compound 15.

Synthesis Example 16 Synthesis of Compound 16

In Synthesis Example 1, Compound 16 was synthesized in the same manner using Intermediate 16 instead of Intermediate 1.
As a result of mass spectrum analysis, it was m / e = 783 with respect to the molecular weight 783 of compound 16.

Synthesis Example 17 Synthesis of Compound 17

In Synthesis Example 1, Compound 17 was synthesized in the same manner using Intermediate 17 instead of Intermediate 1.
As a result of mass spectrum analysis, it was m / e = 857 with respect to the molecular weight 857 of compound 17.

Synthesis Example 18: Synthesis of Compound 18

In Synthesis Example 1, Compound 18 was synthesized in the same manner using Intermediate 18 instead of Intermediate 1.
As a result of mass spectrum analysis, it was m / e = 691 with respect to the molecular weight 691 of Compound 18.

Synthesis Example 19 Synthesis of Compound 19

In Synthesis Example 1, Compound 19 was synthesized in the same manner using Intermediate 19 instead of Intermediate 1.
As a result of mass spectrum analysis, it was m / e = 807 with respect to the molecular weight 807 of compound 19.

Synthesis Example 20 Synthesis of Compound 20

In Synthesis Example 1, Compound 20 was synthesized in the same manner using Intermediate 20 instead of Intermediate 1.
As a result of mass spectrum analysis, m / e = 841 with respect to the molecular weight 841 of Compound 20.

Synthesis Example 21 Synthesis of Compound 21

In Synthesis Example 1, Compound 21 was synthesized in the same manner using Intermediate 21 instead of Intermediate 1.
As a result of mass spectrum analysis, it was m / e = 665 with respect to the molecular weight 665 of compound 21.

Synthesis Example 22 Synthesis of Compound 22

In Synthesis Example 1, Compound 22 was synthesized in the same manner using Intermediate B instead of Intermediate A.
As a result of mass spectrum analysis, it was m / e = 677 with respect to the molecular weight 677 of compound 22.

Synthesis Example 23 Synthesis of Compound 23

In Synthesis Example 4, Compound 23 was synthesized in the same manner using Intermediate B instead of Intermediate A.
As a result of mass spectrum analysis, it was m / e = 677 with respect to the molecular weight 677 of compound 23.

Synthesis Example 24 Synthesis of Compound 24

In Synthesis Example 5, Compound 24 was synthesized in the same manner using Intermediate B instead of Intermediate A.
As a result of mass spectrum analysis, it was m / e = 677 with respect to the molecular weight 677 of compound 24.

Synthesis Example 25 Synthesis of Compound 25

In Synthesis Example 7, Compound 25 was synthesized in the same manner using Intermediate B instead of Intermediate A.
As a result of mass spectrum analysis, it was m / e = 717 with respect to the molecular weight 717 of compound 25.

Synthesis Example 26 Synthesis of Compound 26

In Synthesis Example 13, Compound 26 was synthesized in the same manner using Intermediate B instead of Intermediate A.
As a result of mass spectrum analysis, m / e = 767 with respect to the molecular weight 767 of compound 26.

Synthesis Example 27 Synthesis of Compound 27

In Synthesis Example 10, Compound 27 was synthesized in the same manner using Intermediate B instead of Intermediate A.
As a result of mass spectrum analysis, it was m / e = 839 with respect to the molecular weight 839 of compound 27.

Synthesis Example 28 Synthesis of Compound 28

In Synthesis Example 11, Compound 28 was synthesized in the same manner using Intermediate B instead of Intermediate A.
As a result of mass spectrum analysis, it was m / e = 841 with respect to the molecular weight 841 of Compound 28.

Example 1
Manufacture of organic EL element A glass substrate with 25 mm × 75 mm × 1.1 mm ITO transparent electrode (anode) (manufactured by Geomatic) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, and then UV ozone cleaning for 30 minutes. It was. The film thickness of ITO was 130 nm.
The glass substrate with a transparent electrode after washing was mounted on a substrate holder of a vacuum deposition apparatus. First, compound HA was vapor-deposited so as to cover the transparent electrode on the surface on which the transparent electrode was formed, thereby forming a 5 nm-thick hole injection layer.
Next, Compound 1 was deposited on the hole injection layer to form a first hole transport layer having a thickness of 80 nm.
Next, a compound HT2 was deposited on the first hole transport layer to form a second hole transport layer having a thickness of 10 nm.
Next, a compound BH (host material) and a compound BD (dopant material) were formed on the second hole transport layer by co-evaporation to form a light emitting layer having a thickness of 25 nm. The mass ratio of Compound BH to Compound BD contained in the light emitting layer was 96: 4.
Subsequent to the formation of the light emitting layer, the compound ET1 was deposited to form a first electron transport layer having a thickness of 10 nm, and then the compound ET2 was deposited to form a second electron transport layer having a thickness of 15 nm.
LiF was deposited on the second electron transport layer to form an electron injection layer having a thickness of 1 nm.
Metal Al was vapor-deposited on this electron injection layer to form a metal cathode having a thickness of 80 nm, and an organic EL device was produced.

Measurement of external quantum efficiency The obtained organic EL device was driven at a constant current at a current density of 10 mA / cm ² at room temperature, and the external quantum efficiency (%) was measured using a luminance meter (Spectral Luminance Radiometer CS-1000 manufactured by Minolta). And measured. The results are shown in Table 1.

Examples 2 to 3 and Comparative Examples 1 to 3
An organic EL device was produced in the same manner as in Example 1 except that Compound 7, Compound 15, and Comparative Compounds 1 to 3 were used instead of Compound 1, and the external quantum efficiency of the organic EL device was measured. The results are shown in Table 1.

Compound 1 (Example 1) is a compound obtained by replacing the 9,9-diphenylfluorene skeleton and 9,9′-spirobifluorene skeleton of Comparative Compounds 1 and 2 (Comparative Examples 1 and 2) with a spiroanthracene fluorene skeleton. Compound 7 (Example 2) is a compound obtained by replacing the 9,9-diphenylfluorene skeleton of Comparative Compound 3 (Comparative Example 3) with a spiroanthracene fluorene skeleton.
As is clear from the comparison between Example 1 and Comparative Examples 1 and 2 and the comparison between Example 2 and Comparative Example 3, the 9,9-diphenylfluorene skeleton and 9,9′-spirobifluorene of the comparative compound The compound of the present invention in which the skeleton is replaced with the spiroanthracene fluorene skeleton provides an organic EL device in which the light emission efficiency (external quantum efficiency) is further improved as compared with an organic EL device containing a comparative compound. The effect of improving the luminous efficiency of the compound of the present invention is considered to be due to the fact that the hole mobility is higher than that of the comparative compound.

DESCRIPTION OF SYMBOLS 1 Organic EL element 2 Board | substrate 3 Anode 4 Cathode 5 Light emitting layer 6 Anode side organic layer 7 Cathode side organic layer 10 Light emitting unit

Claims

A compound represented by the following formula (1).

(Where
R 1 to R 8 and R 11 to R 18 are each independently a hydrogen atom or a substituent, two adjacent groups selected from R 1 to R 4, two adjacent groups selected from R 5 to R 8 , Two adjacent groups selected from R 11 to R 14 and two adjacent groups selected from R 15 to R 18 may be bonded to each other to form a ring structure.
However, one selected from R 1 to R 8 and R 11 to R 18 represents a single bond bonded to *, or the ring-forming atom of the ring structure is bonded to *.
R 21 and R 22 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring. It is a heteroaryl group having 5 to 30 atoms.
L 1 , L 2 , and L 3 are each independently a single bond, 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. It is.
Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted oxygen-containing heteroaryl group having 5 to 30 ring atoms, or substituted or unsubstituted. A sulfur-containing heteroaryl group having 5 to 30 ring atoms.
The substituent represented by R 1 to R 8 and R 11 to R 18 is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, substituted or unsubstituted Unsubstituted aryl group having 6 to 30 ring carbon atoms, substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, substituted or unsubstituted aralkyl group having 7 to 36 carbon atoms, substituted or unsubstituted An alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and a substituted or unsubstituted ring carbon number 6 A mono-, di- or tri-substituted silyl group having a substituent selected from aryl groups of 1 to 30; a substituted or unsubstituted haloalkyl group having 1 to 30 carbon atoms; a substituted or unsubstituted carbon number Haloalkoxy groups to 30, a halogen atom, a cyano group, or a nitro group. )
2. The compound according to claim 1, wherein one selected from R 1 to R 8 and R 11 to R 18 is a single bond bonded to *.
The compound according to claim 1 or 2, wherein one selected from R 2 to R 7 , R 12 , and R 17 is a single bond bonded to *.
The compound according to any one of claims 1 to 3, wherein one selected from R 2 to R 7 is a single bond bonded to *.
The compound according to any one of claims 1 to 4, which is represented by the following formula (2):

(In the formula, R 1 , R 3 to R 8 , R 11 to R 18 , R 21 , R 22 , L 1 to L 3 , Ar 1 and Ar 2 are the same as described above.)
The compound according to any one of claims 1 to 4, which is represented by the following formula (3):

(In the formula, R 1 , R 2 , R 4 to R 8 , R 11 to R 18 , R 21 , R 22 , L 1 to L 3 , Ar 1 , and Ar 2 are the same as above.)
The compound according to any one of claims 1 to 4, which is represented by the following formula (4):

(Wherein R 1 to R 3 , R 5 to R 8 , R 11 to R 18 , R 21 , R 22 , L 1 to L 3 , Ar 1 , and Ar 2 are the same as above).
One of Ar 1 and Ar 2 is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and the other is a substituted or unsubstituted oxygen-containing heteroaryl group having 5 to 30 ring atoms or substituted or unsubstituted The compound according to any one of claims 1 to 7, which is a substituted sulfur-containing heteroaryl group having 5 to 30 ring atoms.
The compound according to any one of claims 1 to 7, wherein Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
Ar 1 and Ar 2 are each independently a substituted or unsubstituted oxygen-containing heteroaryl group having 5 to 30 ring atoms or a substituted or unsubstituted sulfur-containing heteroaryl group having 5 to 30 ring atoms. Item 8. The compound according to any one of Items 1 to 7.
The aryl group of the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms represented by Ar 1 and / or Ar 2 is a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, an acenaphthylenyl group, a biphenylenyl group, a fluorenyl group. S-indacenyl group, as-indacenyl group, anthryl group, benzoanthryl group, aceantrirenyl group, phenanthryl group, benzophenanthryl group, phenalenyl group, naphthacenyl group, fluoranthenyl group, pyrenyl group, chrysenyl group, The compound according to any one of claims 1 to 9, which is selected from a benzocrisenyl group, a triphenylenyl group, a pentacenyl group, a picenyl group, and a pentaphenyl group.
The substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms represented by Ar 1 and / or Ar 2 is a phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4. -Yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, 2-phenanthryl group, 9-phenanthryl group, 2-triphenylenyl group, 9 , 9′-spirobifluoren-2-yl group, 9,9′-spirobifluoren-4-yl group, 9,9-diphenylfluoren-2-yl group, 9,9-diphenylfluoren-4-yl group 9,9-dimethylfluoren-2-yl group, 9,9-dimethylfluoren-4-yl group, 10,10-dimethyl (anthracene-9,9′-fluoren) -2′-yl group, and 1 , 10 Dimethyl (anthracene-9,9'-fluorene) -4'-yl A compound according to claim 1 to 9 and 11 to be selected from the group.
The oxygen-containing heteroaryl group of the substituted or unsubstituted oxygen-containing heteroaryl group having 5 to 30 ring atoms represented by Ar 1 and / or Ar 2 is a furyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a xanthenyl group. Benzofuranyl group, dibenzofuranyl group, naphthobenzofuranyl group, benzoxazolyl group, benzoisoxazolyl group, and phenoxazinyl group,
The sulfur-containing heteroaryl group of the substituted or unsubstituted sulfur-containing heteroaryl group having 5 to 30 ring atoms represented by Ar 1 and / or Ar 2 is a thienyl group, thiazolyl group, isothiazolyl group, thiadiazolyl group, benzothio The compound according to claims 1 to 8 and 10, which is selected from a phenyl group, a dibenzothiophenyl group, a naphthobenzothiophenyl group, a benzothiazolyl group, a benzoisothiazolyl group, and a phenothiazinyl group.
The oxygen-containing heteroaryl group having 5 to 30 ring atoms represented by Ar 1 and / or Ar 2 is a dibenzofuranyl group or a naphthobenzofuranyl group, and the sulfur-containing heteroaryl having 5 to 30 ring atoms The compound according to claim 1, wherein the group is a dibenzothiophenyl group or a naphthobenzothiophenyl group.
One of R 21 and claim 1 ~ 14 R 22 are each independently substituted or unsubstituted C 1 -C 30 alkyl group or a substituted or unsubstituted ring aryl group having 6 to 30 1 The compound according to item.
The compound according to any one of claims 1 to 15, wherein R 21 and R 22 do not bind to each other and thus do not form a ring structure.
The compound according to any one of claims 1 to 16, wherein R 21 and R 22 are selected from a methyl group and a phenyl group.
The compound according to any one of claims 1 to 17, wherein L 1 and L 2 are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms.
The compound according to any one of claims 1 to 18, wherein the arylene group of the substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms represented by L 1 and / or L 2 is selected from the following formulae.
The compound according to any one of claims 1 to 19, wherein one or both of L 1 and L 2 is a single bond.
The compound according to any one of claims 1 to 20, wherein L 3 is a single bond or a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms.
The compound according to any one of claims 1 to 21, wherein the arylene group of the substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms represented by L 3 is selected from the following formulae.
The compound according to any one of claims 1 to 22, wherein L 3 is a single bond or a phenylene group.
The compound according to any one of claims 1 to 23, wherein L 1 and L 2 , L 1 and L 3 , and L 2 and L 3 are not bonded to each other.
The compound according to any one of claims 1 to 24, wherein R 1 to R 8 and R 11 to R 18 which do not represent a single bond bonded to * and do not form the ring structure are a hydrogen atom.
The compound according to any one of claims 1 to 25, wherein one selected from R 1 to R 7 and R 11 to R 18 is a single bond bonded to *, and the rest are all hydrogen atoms.
An organic electroluminescent element material comprising the compound according to any one of claims 1 to 26.
An organic electroluminescent device comprising a cathode, an anode, and an organic layer disposed between the cathode and the anode, wherein the organic layer comprises a light emitting layer, and at least one of the organic layers is at least one layer. Organic electroluminescent element containing the compound of any one of these.
The organic electroluminescence device according to claim 28, wherein the organic layer includes a hole transport layer, and the hole transport layer includes the compound.
The hole transport layer includes a first hole transport layer on the anode side and a second hole transport layer on the cathode side, and one or both of the first hole transport layer and the second hole transport layer is the compound. The organic electroluminescent element of Claim 29 containing.
An electronic device comprising the organic electroluminescence element according to any one of claims 28 to 30.