WO2018034242A1

WO2018034242A1 - Compound, organic electroluminescent element material, organic electroluminescent element, and electronic device

Info

Publication number: WO2018034242A1
Application number: PCT/JP2017/029157
Authority: WO
Inventors: 裕基中野; 祐一西前; 匡羽毛田; 河村　昌宏
Original assignee: 出光興産株式会社
Priority date: 2016-08-19
Filing date: 2017-08-10
Publication date: 2018-02-22
Also published as: JPWO2018034242A1

Abstract

A compound represented by formula (1) (in formula (1), the dotted lines, A-D, and R¹-R¹⁰ are as defined in the specification) yields a high-performance organic electroluminescent element.

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, an organic electroluminescence element, and an electronic device.

Generally, an organic electroluminescence element (organic EL element) is composed of an anode, a cathode, and an organic thin film layer including one or more layers sandwiched between the anode and the cathode. The organic thin film layer includes a light emitting layer, and exciton energy generated by recombination of holes and electrons injected into the light emitting layer is converted into light emission.

It is known that the light emitting layer is a host / dopant light emitting layer in which a host material is doped with a light emitting material (dopant material). In the host / dopant light emitting layer, excitons can be efficiently generated from the charge injected into the host. And the energy of the produced | generated exciton can be moved to a dopant, and highly efficient light emission can be obtained from a dopant.

In recent years, in order to further improve the performance of organic EL elements, further research has been conducted on host / dopant systems, and search for suitable host materials and other materials for organic EL elements continues.

As such an organic EL device material, Patent Document 1 describes a compound in which indole is essential to be condensed at the 2,3-position of phenanthrene. Patent Document 2 is a compound in which indole is condensed at the 2,3-position of phenanthrene, and Patent Document 3 is indispensable that benzofuran or benzothiophene is condensed at the 2,3-position of phenanthrene. A certain compound, Patent Document 4, describes a compound in which it is essential that benzofuran, benzothiophene, or other heterocycle is condensed at the 2,3-position of phenanthrene. It is described that the compounds described in Patent Documents 2 to 4 can be used as host materials for phosphorescent organic EL devices.

However, there is still a demand for compounds that further improve the characteristics of organic EL devices.

CN106033748A US2014 / 0117326A1 US2014 / 0117331A1 US2014 / 0103300A1

The present invention has been made to solve the above-mentioned problems, and an object of the present invention is to provide a novel compound that can realize an organic EL device having good characteristics.

As a result of intensive studies to achieve the above object, the present inventors have found that a compound represented by the following formula (1) realizes a high-performance organic EL device.

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

((Where
The broken lines indicate adjacent groups R ¹ and R ² included in A, adjacent groups R ³ and R ⁴ included in B, adjacent groups R ⁵ and R ⁶ included in C, and adjacent groups R ⁷ and R ⁸ included in D. , Each adjacent group selected from the adjacent groups R ⁹ and R ¹⁰ contained in E may or may not be bonded to the group represented by the formula (2) or (3);
The adjacent group contained in one selected from A to E is bonded to the group represented by the formula (2);
The adjacent groups contained in 1 to 4 groups selected from the remaining A to E are each independently bonded to the group represented by the formula (3);
When the adjacent group is bonded to the group represented by the formula (2), one of the adjacent groups is bonded to * 1, and the other is bonded to * 2.
When the adjacent group is bonded to the group represented by the formula (3), one of the adjacent groups is bonded to * 3, and the other is bonded to * 4.
R ¹ to R ¹⁰ represent a bond bonded to * 1, * 2, * 3 or * 4 when bonded to a group represented by the formula (2) or (3);
R ¹ to R ¹⁰ each independently represent a hydrogen atom or a substituent when not bonded to the group represented by the formula (2) or (3), and two adjacent groups are bonded to each other, A substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 18 carbon atoms, a substituted or unsubstituted aromatic heterocyclic ring having 5 to 18 ring atoms, or a substituted or unsubstituted ring atom having 5 to 18 ring atoms The aliphatic heterocyclic ring may be formed. However, it excludes when forming group represented by Formula (2) or (3). )

(In the formula (2),
X is O, S, or NL ¹ -R ¹⁵ ;
L ¹ is a single bond or a linking group;
R ¹⁵ is a hydrogen atom or a substituent,
R ¹¹ to R ¹⁴ are each independently a hydrogen atom or a substituent, and adjacent two groups are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 18 ring carbon atoms, A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 18 carbon atoms, a substituted or unsubstituted aliphatic heterocyclic ring having 5 to 18 ring atoms, or a substituted or unsubstituted aromatic ring having 6 ring atoms A group heterocycle may be formed,
In formula (3),
Y is O, S, NL ² -R ²⁵ , or CR ²⁶ R ²⁷ ;
L ² is a single bond or a linking group,
R ²⁵ is a hydrogen atom or a substituent,
R ²⁶ and R ²⁷ are each independently a hydrogen atom or a substituent, and bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 18 ring carbon atoms or a substituted or unsubstituted ring. An aliphatic heterocyclic ring having 5 to 18 ring atoms may be formed,
R ²¹ to R ²⁴ are each independently a hydrogen atom or a substituent, and adjacent two groups are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 18 ring carbon atoms, A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 18 carbon atoms, a substituted or unsubstituted aliphatic heterocyclic ring having 5 to 18 ring atoms, or a substituted or unsubstituted aromatic ring having 6 ring atoms A group heterocycle may be formed. ))

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 thin film layer disposed between the cathode and the anode, wherein the organic thin film layer includes one or more layers. The organic thin film layer includes a light emitting layer, and at least one of the organic thin film layers provides an organic electroluminescence device including the compound (1).

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

Compound (1) can realize an organic EL device having good characteristics.

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

In the present specification, the “carbon number XX to YY” in the expression “substituted or unsubstituted ZZ group having XX to YY” represents the number of carbon atoms in the case where the ZZ group is unsubstituted. The carbon number of the substituent in the case where it is present is not included.

In this specification, “atom number XX to YY” in the expression “a ZZ group having a substituted or unsubstituted atom number XX to YY” represents the number of atoms when the ZZ group is unsubstituted. In this case, the number of substituent atoms is not included.

In the present specification, the term “unsubstituted ZZ group” in the case of “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 this specification, the “ring-forming carbon number” means the ring itself of a compound having a structure in which atoms are bonded in a cyclic manner (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, or a heterocyclic compound). This represents the number of carbon atoms among the constituent atoms. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the ring-forming carbon. The “ring-forming carbon number” described below is the same 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. Further, when an alkyl group is substituted as a substituent on the benzene ring or naphthalene ring, the carbon number of the alkyl group is not included in the number of ring-forming carbons. In addition, for example, when a fluorene ring is bonded to the fluorene ring as a substituent (including a spirofluorene ring), the carbon number of the fluorene ring as a substituent is not included in the ring-forming carbon number.

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

In the present specification, unless otherwise specified, an arbitrary substituent referred to as “substituted or unsubstituted” is an alkyl group having 1 to 50 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms; A cycloalkyl group having a number of 3 to 50, preferably 3 to 10, more preferably 3 to 8, more preferably 5 or 6, and a ring forming carbon number of 6 to 50, preferably 6 to 25, more preferably 6 to 18. An aryl group; an aralkyl group having 6 to 50 ring-forming carbon atoms, preferably 6 to 25, more preferably 6 to 18 carbon atoms, and an aryl group having 7 to 51 carbon atoms, preferably 7 to 30 carbon atoms, and more preferably 7 to 20 carbon atoms; An amino group; selected from an alkyl group having 1 to 50 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms, and an aryl group having 6 to 50 ring carbon atoms, preferably 6 to 25 carbon atoms, more preferably 6 to 18 carbon atoms. Mono-substituted or di-substituted amino group having an alkyl group; an alkoxy group having an alkyl group having 1 to 50 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms; 6 to 50 ring carbon atoms, preferably 6 carbon atoms. An aryloxy group having an aryl group of ˜25, more preferably 6-18; an alkyl group having 1-50, preferably 1-18, more preferably 1-8, and a ring carbon number of 6-50, preferably A mono-, di- or tri-substituted silyl group having a substituent selected from 6 to 25, more preferably 6 to 18 aryl groups; 1 to 50 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms A haloalkyl group; a haloalkoxy group having a haloalkyl group having 1 to 50 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms; 5 to 50 ring forming atoms, preferably 5 to 24 carbon atoms; Preferably an aromatic or non-aromatic heterocyclic group 5-13; a group selected from and nitro group, a halogen atom, a cyano group.
The optional substituent is more preferably an alkyl group having 1 to 50 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms; 3 to 50 ring carbon atoms, preferably 3 to 10 carbon atoms, more preferably 3 carbon atoms. -8, more preferably 5 or 6 cycloalkyl group; 6 to 50 ring carbon atoms, preferably 6 to 25, more preferably 6 to 18 aryl groups; 1 to 50 carbon atoms, preferably 1 to 18 carbon atoms; More preferably a mono- or di-substituted amino group having a substituent selected from an alkyl group having 1 to 8 and an aryl group having 6 to 50, preferably 6 to 25, more preferably 6 to 18 ring carbon atoms; It is selected from an aromatic heterocyclic group having 5 to 50 atoms, preferably 5 to 24, more preferably 5 to 13; a halogen atom; and a cyano group.
The details of the optional substituent are the same as those described below for R ¹ to R ¹⁰ . The above arbitrary substituents may be further substituted with the above arbitrary substituents. Moreover, adjacent arbitrary substituents may combine to form a ring.

The compound which concerns on 1 aspect of this invention is represented by Formula (1).

Compound (1) includes compounds represented by the following formulas (10-1) to (10-16). In formulas (10-1) to (10-16), the curves shown by solid lines indicate that the adjacent groups contained in A to E are bonded to the groups represented by formula (2) or (3), respectively. Indicates that a ring is formed.

In a preferred embodiment of the present invention, the compound (1) is preferably represented by the formulas (10-2), (10-6), (10-7), (10-11), (10-13), (10-14) ) And (10-16), more preferably the formulas (10-6), (10-7), (10-11), (10-13), (10-14) and (10 -16), more preferably represented by any one of formulas (10-11), (10-13), (10-14) and (10-16), and particularly preferably represented by formula (10-16). −13), (10-14) and (10-16).

In another preferred embodiment of the present invention, the compound (1) is represented by the formula (20) or (30).

(Wherein R ¹ to R ⁴ , R ⁷ to R ¹⁰ , R ¹¹ to R ¹⁴ , and X are as described above, and a curve indicated by a broken line is a group selected from A, B, D, and E 1 to (It represents that the adjacent groups contained in each of the four are independently bonded to the group represented by the formula (3).)

The compound represented by the formula (20) includes compounds represented by the formulas (20-1) to (20-15). In the formulas (20-1) to (20-15), the curves shown by solid lines are represented by the formula (3) in which the adjacent groups contained in each of A, B, D, and E are independently represented. Represents a bond to a group.

The compound represented by the formula (20) is represented by the formula (20-3), (20-6), (20-9), (20-10), (20-12), (20-14), or ( 20-15) is preferable, and a formula (20-20) or (20-21) is particularly preferable.

The compound represented by the formula (30) includes compounds represented by the formulas (30-1) to (30-15). In the formulas (30-1) to (30-15), the curves shown by solid lines are represented by the formula (3) in which the adjacent groups contained in each of A, B, D, and E are independently represented. Represents bonding to a group.

The compound represented by the formula (30) is represented by the formula (30-3), (30-6), (30-9), (30-10), (30-12), (30-14), or ( 30-15), and particularly preferably represented by the formula (30-20) or (30-21).

In another preferred embodiment of the present invention, the compound (1) is represented by the formula (40), (50) or (60).

(Where
R ¹ to R ¹⁰ , R ¹¹ to R ¹⁴ , and X are as described above,
In the formulas (40) and (50), the curve indicated by a broken line shows that each of the adjacent groups contained in 1 to 4 selected from A to C and E is independently represented by the formula (3). Represents a bond to the group
In the formula (60), the curve indicated by the broken line shows that the adjacent groups contained in each of 1 to 4 selected from A to D are independently bonded to the group represented by the formula (3). Represents that )

The compound represented by the formula (40) includes compounds represented by the formulas (40-1) to (40-15). In the formulas (40-1) to (40-15), the curves indicated by solid lines are represented by the formula (3) in which the adjacent groups contained in each of A, B, C, and E are independently represented. Represents a bond to a group.

The compound represented by the formula (40) is represented by the formula (40-2), (40-9), (40-10), (40-11), (40-13), (40-14), or ( 40-15), and particularly preferably represented by any one of formulas (40-20) to (40-23).

The compound represented by the formula (50) includes compounds represented by the formulas (50-1) to (50-15). In the formulas (50-1) to (50-15), in the curves shown by solid lines, the adjacent groups contained in each of A, B, C and E are each independently represented by the formula (3). Represents a bond to a group.

The compound represented by the formula (50) is represented by the formula (50-2), (50-9), (50-10), (50-11), (50-13), (50-14), or ( 50-15) and particularly preferably any one of formulas (50-20) to (50-23).

The compound represented by the formula (60) includes compounds represented by the formulas (60-1) to (60-15). In the formulas (60-1) to (60-15), in the curves shown by solid lines, the adjacent groups contained in each of A, B, C and D are independently represented by the formula (3). Represents a bond to a group.

The compound represented by the formula (60) is preferably represented by any one of the formulas (60-12) to (60-15).

In another preferred embodiment of the present invention, the compound (1) is represented by the formula (70) or (80).

(Wherein R ¹ to R ⁴ , R ⁷ to R ¹⁰ , R ²¹ to R ²⁴ , and Y are as described above, and the curve indicated by a broken line is one selected from A, B, D, and E) That the adjacent group contained in is bonded to the group represented by the formula (2), and the adjacent groups contained in the remaining 1 to 3 are each independently represented by the formula (3). It represents that it is bonded to the group.)

Hereinafter, the compounds of the present invention represented by the above formulas will be described in more detail.

In the above formula, the curves shown by broken lines are included in the adjacent groups R ¹ and R ² included in A, the adjacent groups R ³ and R ⁴ included in B, and the adjacent groups R ⁵ and R ⁶ and D included in C. Each adjacent group selected from the adjacent groups R ⁷ and R ⁸ and the adjacent groups R ⁹ and R ¹⁰ contained in E may be bonded to or bonded to the group represented by the formula (2) or (3) Indicates that you do not have to.
In the compound of the present invention, two groups selected from R ² and R ³ , R ⁴ and R ⁵ , R ⁶ and R ⁷ , R ⁸ and R ⁹ , and R ¹⁰ and R ¹ are represented by the formula (2) or (3 ) Or a group represented by the formula (2) or (3). That is, in the compound of the present invention, the central phenanthrene structure at the 2nd and 3rd positions, the 4th and 5th positions, the 6th and 7th positions, the 8th and 9th positions, and the 10th and 1st positions, The group represented by 3) is not bonded.

In one embodiment of the present invention, the adjacent group contained in one selected from A to D is preferably bonded to the group represented by the formula (2), and the adjacent group contained in B or C is represented by the formula It is more preferable to bond to the group represented by (2).

In another embodiment of the present invention, it is preferable that the adjacent groups contained in 1 to 3 selected from A to D are independently bonded to the group represented by the formula (3), and A, B More preferably, the adjacent groups contained in 1 to 3 groups selected from A and C or A, C and D are each independently bonded to the group represented by the formula (3).

In another embodiment of the present invention, the adjacent group contained in one of B or C is bonded to the group represented by the formula (2), and the other of B or C, 1-3 selected from A and D It is preferable that the adjacent groups included are each independently bonded to the group represented by the formula (3), and the adjacent groups included in one or two selected from A and D are each independently More preferably, it is bonded to a group represented by the formula (3).

In another embodiment of the present invention, the group represented by the formula (2) and the group represented by the formula (3) are preferably bonded to benzene rings having different central phenanthrene structures.

R ¹ to R ¹⁰ represent a bond bonded to * 1, * 2, * 3 or * 4 when bonded to the group represented by the formula (2) or (3). That is, the group represented by the formula (2) and the group represented by the formula (3) are directly bonded to the benzene ring of the central phenanthrene structure.

R ¹ to R ¹⁰ each independently represent a hydrogen atom or a substituent when not bonded to the group represented by the formula (2) or (3). Two adjacent substituents are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 18 ring carbon atoms, a substituted or unsubstituted aromatic heterocyclic ring having 5 to 18 ring atoms, or A substituted or unsubstituted aliphatic heterocyclic ring having 5 to 18 ring atoms may be formed. However, it excludes when forming group represented by Formula (2) or (3). In one embodiment of the present invention, two adjacent substituents are not bonded to each other and thus do not have to form a ring. In another embodiment of the present invention, R ¹ to R ^{10 that} are not bonded to the group represented by formula (2) or (3) are preferably hydrogen atoms.

The substituent represented by R ¹ to R ¹⁰ is an alkyl group having 1 to 50 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms; 3 to 50 ring carbon atoms, preferably 3 to 10 carbon atoms, and more preferably. Is a cycloalkyl group having 3 to 8, more preferably 5 or 6; an aryl group having 6 to 50 ring carbon atoms, preferably 6 to 25, more preferably 6 to 18 ring atoms; 6 to 50 ring carbon atoms, preferably Aralkyl group having 6 to 25, more preferably 6 to 18 aryl groups having 6 to 18 carbon atoms, preferably 7 to 30, more preferably 7 to 20 carbon atoms; amino group; 1 to 50 carbon atoms, preferably 1 to A mono- or di-substituted amino group having a substituent selected from 18, more preferably an alkyl group having 1 to 8 and an aryl group having 6 to 50, preferably 6 to 25, more preferably 6 to 18 ring carbon atoms; Carbon number An alkoxy group having an alkyl group of ˜50, preferably 1 to 18, more preferably 1 to 8; an aryloxy having an aryl group having 6 to 50 ring carbon atoms, preferably 6 to 25, more preferably 6 to 18 Group: selected from an alkyl group having 1 to 50 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms and an aryl group having 6 to 50 ring carbon atoms, preferably 6 to 25 carbon atoms, more preferably 6 to 18 carbon atoms. Mono-substituted, di-substituted or tri-substituted silyl groups having a substituent; a haloalkyl group having 1 to 50 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms; 1 to 50 carbon atoms, preferably 1 to 18 carbon atoms, and more A haloalkoxy group preferably having 1 to 8 haloalkyl groups; an aromatic or non-aromatic heterocyclic group having 5 to 50, preferably 5 to 24, more preferably 5 to 13 ring-forming atoms Is a group selected from and nitro group, a halogen atom, a cyano group. The above substituent may be further substituted with the above-described substituent.

The substituent represented by R ¹ to R ¹⁰ is preferably an alkyl group having 1 to 50 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms; 3 to 50 ring carbon atoms, preferably 3 to 10 carbon atoms. More preferably 3 to 8, more preferably 5 or 6 cycloalkyl group; ring-forming carbon number 6 to 50, preferably 6 to 25, more preferably 6 to 18 aryl group; carbon number 1 to 50, preferably Is mono- or di-substituted having a substituent selected from an alkyl group having 1 to 18, more preferably 1 to 8 and an aryl group having 6 to 50, preferably 6 to 25, more preferably 6 to 18 ring carbon atoms. An amino group; an aromatic heterocyclic group having 5 to 50 ring-forming atoms, preferably 5 to 24, more preferably 5 to 13; a halogen atom; and a cyano group, more preferably 1 to 50 carbon atoms, Preferably An alkyl group having 1 to 8, more preferably 1 to 8, an aryl group having 6 to 50 ring carbon atoms, preferably 6 to 25, more preferably 6 to 18 carbon atoms; 1 to 50 carbon atoms, preferably 1 to 18 carbon atoms, and more. A mono- or di-substituted amino group having a substituent preferably selected from an alkyl group having 1 to 8 and an aryl group having 6 to 50, preferably 6 to 25, more preferably 6 to 18 ring carbon atoms; An aromatic heterocyclic group having a number of 5 to 50, preferably 5 to 24, more preferably 5 to 13; and a cyano group, and more preferably a ring forming carbon number of 6 to 50, preferably 6 to 25, more Preferably, it is selected from 6-18 aryl groups; 5-50 ring-forming atoms, preferably 5-24, more preferably 5-13 aromatic heterocyclic groups; and cyano groups.

Examples of the alkyl group having 1 to 50 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group (isomers). Group), hexyl group (including isomer group), heptyl group (including isomer group), octyl group (including isomer group), nonyl group (including isomer group), decyl group (isomer) Group), undecyl group (including isomer group), dodecyl group (including isomer group), and the like, such as 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 preferable, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group Group and t-bu More preferably group, further preferably a methyl group and t- butyl group.

Examples of the cycloalkyl group having 3 to 50 ring carbon atoms include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.

Examples of the aryl group having 6 to 50 ring carbon atoms include phenyl group, biphenylyl group, terphenylyl group, biphenylenyl group, naphthyl group, acenaphthylenyl group, anthryl group, benzoanthryl group, aceanthryl group, phenanthryl group, benzophenyl group, Examples include nantril group, phenalenyl group, fluorenyl group, pentacenyl group, picenyl group, pentaphenyl group, pyrenyl group, chrysenyl group, benzocrisenyl group, s-indacenyl group, as-indacenyl group, fluoranthenyl group, and perylenyl group. A phenyl group, a biphenylyl group, a terphenylyl group, and a naphthyl group are preferable, a phenyl group, a biphenylyl group, and a naphthyl group are more preferable, and a phenyl group is more preferable.
As the substituted aryl group having 6 to 50 ring carbon atoms, 9,9-dimethylfluorenyl group and 9,9-diphenylfluorenyl group are preferable.

The aryl group having 6 to 50 ring carbon atoms contained in the aralkyl group having 7 to 51 carbon atoms is the same as the aryl group having 6 to 50 ring carbon atoms, and the alkyl part of the aralkyl group has The alkyl group is selected so as to satisfy 7 to 51. Examples of the aralkyl group having 7 to 51 carbon atoms include a benzyl group, a phenethyl group, and a phenylpropyl group, and a benzyl group is preferable.

The mono- or di-substituted amino group has an alkyl group having 1 to 50 carbon atoms and an aryl group having 6 to 50 ring carbon atoms, and the alkyl group having 1 to 50 carbon atoms and the ring group having 6 to 50 carbon atoms. This is the same as the aryl group. Examples of the mono- or di-substituted amino group include a dialkylamino group, a diarylamino group, and an alkylarylamino group.

The alkyl group having 1 to 50 carbon atoms contained in the alkoxy group is the same as the alkyl group having 1 to 50 carbon atoms. 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 more preferable.

The aryl group having 6 to 50 ring carbon atoms contained in the aryloxy group is the same as the aryl group having 6 to 50 ring carbon atoms. 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-substituted, di-substituted, or tri-substituted silyl group has an alkyl group having 1 to 50 carbon atoms and an aryl group having 6 to 50 ring carbon atoms, and the alkyl group having 1 to 50 carbon atoms and the ring group having 6 to 50 carbon atoms. This is the same as the aryl group. 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.

The haloalkyl group having 1 to 50 carbon atoms is at least one of the above alkyl groups having 1 to 50 carbon atoms, preferably 1 to 7 hydrogen atoms, or all hydrogen atoms are fluorine atoms, chlorine atoms, bromine atoms. And a group obtained by substitution with a fluorine atom, preferably a fluoroalkyl group having 1 to 50 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms. A heptafluoropropyl group (including isomers), a pentafluoroethyl group, a 2,2,2-trifluoroethyl group, and a trifluoromethyl group are more preferable, and a pentafluoroethyl group, 2,2,2-trifluoroethyl group is more preferable. And a trifluoromethyl group are more preferable, and a trifluoromethyl group is particularly preferable.

The haloalkyl group having 1 to 50 carbon atoms of the haloalkoxy group is the same as the haloalkyl group having 1 to 50 carbon atoms, and has 1 to 50 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms. A fluoroalkoxy group is preferred, a heptafluoropropoxy group (including isomers), a pentafluoroethoxy group, a 2,2,2-trifluoroethoxy group, and a trifluoromethoxy group are more preferred, and a pentafluoroethoxy group, 2,2 , 2-trifluoroethoxy group and trifluoromethoxy group are more preferable, and trifluoromethoxy group is particularly preferable.

The aromatic or non-aromatic heterocyclic group having 5 to 50 ring atoms is 1 to 5, preferably 1 to 3, more preferably 1 to 2 ring-forming heteroatoms such as nitrogen atom, sulfur Includes atoms and oxygen atoms.
Examples of the aromatic heterocyclic group include pyrrolyl, furyl, thienyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl, isoxazolyl, isothiazolyl Group, oxadiazolyl group, thiadiazolyl group, triazolyl group, indolyl group, isoindolyl group, benzofuranyl group, isobenzofuranyl group, benzothiophenyl group (benzothienyl group, the same shall apply hereinafter), indolizinyl group, quinolidinyl group, quinolyl group, isoquinolyl group , Cinnolyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, benzoimidazolyl group, benzoxazolyl group, benzothiazolyl group, indazolyl group, benzisoxazolyl group, benzoisothiazolyl , Dibenzofuranyl group, naphthobenzofuranyl group, dibenzothiophenyl group (dibenzothienyl group, the same applies hereinafter), naphthobenzothiophenyl group (naphthobenzothienyl group, the same applies hereinafter), carbazolyl group (N-carbazolyl group and C- Carbazolyl group, the same applies hereinafter), benzocarbazolyl group (benzo-N-carbazolyl group and benzo-C-carbazolyl group, the same applies hereinafter), phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, pheno Examples include thiazinyl, phenoxazinyl, and xanthenyl groups. Furyl, thienyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, benzofuranyl, benzothiophenyl, dibenzofuranyl, naphthobenzofuran Nyl group, dibenzothi Phenyl group, naphthobenzothiophenyl group, carbazolyl group, and benzocarbazolyl group are preferable, thienyl group, benzothiophenyl group, dibenzofuranyl group, naphthobenzofuranyl group, dibenzothiophenyl group, naphthobenzothiophenyl group More preferred are a carbazolyl group and a benzocarbazolyl group. Examples of the substituted heteroaryl group include N-phenylcarbazolyl group, N-biphenylylcarbazolyl group, N-phenylphenylcarbazolyl group, N-naphthylcarbazolyl group, phenyldibenzofuranyl group, And a phenyldibenzothiophenyl group (phenyldibenzothienyl group) is preferable.
As a non-aromatic heterocyclic group, the group which hydrogenated the aromatic ring of the said aromatic heterocyclic group, and converted into the aliphatic ring is mentioned, for example.

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

Examples of the aliphatic hydrocarbon ring having 5 to 18 ring carbon atoms include cyclopentene, cyclopentadiene, cyclohexene, cyclohexadiene, and biphenylene, naphthalene, acenaphthylene, anthracene, benzoanthracene, aceanthrylene, phenanthrene, benzo Examples include phenanthrene, phenalene, fluorene, pyrene, chrysene, s-indacene, as-indacene, fluoranthene and the like, which are obtained by hydrogenating an aromatic ring of an aromatic hydrocarbon having 6 to 18 carbon atoms and converting it into an aliphatic ring. It is done.

Examples of the aromatic heterocyclic ring having 5 to 18 ring atoms include pyrrole, furan, thiophene, pyridine, pyridazine, pyrimidine, pyrazine, triazine, imidazoline, oxazole, thiazole, pyrazole, isoxazole, isothiazole, oxadi Azole, thiadiazole, triazole, indole, isoindole, benzofuran, isobenzofuran, benzothiophene, indolizine, quinolidine, quinoline, isoquinoline, cinnoline, phthalazine, quinazoline, quinoxaline, benzimidazole, benzoxazole, benzothiazole, indazole, benzisoxa Sol, benzoisothiazole, dibenzofuran, naphthobenzofuran, dibenzothiophene, naphthobenzothiophene, carbazole, Down zone carbazole, phenanthridine, acridine, phenanthroline, phenazine, phenothiazine, phenoxazine, xanthene, and the like.

Examples of the aliphatic heterocyclic ring having 5 to 18 ring atoms include a ring obtained by hydrogenating an aromatic ring of the aromatic heterocyclic ring having 5 to 18 ring atoms and converting it to an aliphatic ring.

In the formula (2), X represents O, S, or NL ¹ -R ¹⁵ , preferably NL ¹ -R ¹⁵ , L ¹ is a single bond or a linking group, and R ¹⁵ is a hydrogen atom or It is a substituent.
In one embodiment of the present invention, L ¹ is preferably a single bond, and in another embodiment, L ¹ is preferably a linking group. In one embodiment of the present invention, R ¹⁵ is preferably a hydrogen atom, and in another embodiment, R ¹⁵ is preferably a substituent.

The linking group represented by L ¹ is a substituted or unsubstituted arylene group having 6 to 50, preferably 6 to 25, more preferably 6 to 18 ring forming carbon atoms, or a substituted or unsubstituted ring forming carbon atom number of 5 to 50, preferably Is a heteroarylene group of 5 to 24, more preferably 5 to 13.
The arylene group is a divalent group obtained by removing one hydrogen atom from an aryl group having 6 to 50 ring carbon atoms described for R ¹ to R ¹⁰ , and the heteroarylene group is R ¹ to R 10. ^{And a} divalent group obtained by removing one hydrogen atom from an aromatic heterocyclic group having 5 to 50 ring atoms as described for No. 10.
L ¹ is preferably an arylene group having 6 to 50 ring carbon atoms, preferably 6 to 25 carbon atoms, more preferably 6 to 18 carbon atoms, more preferably a phenylene group (including an isomer group), a biphenylene group (an isomer group). A terphenylene group (including an isomer group).

The substituent represented by R ¹⁵ is the same as the substituent described for R ¹ to R ¹⁰ , and is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted ring group having 6 to 50 carbon atoms. An aryl group; a substituted or unsubstituted aralkyl group having 7 to 51 carbon atoms having an aryl group having 6 to 50 ring forming carbon atoms; and a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 ring atoms The group is preferably selected from the group, more preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 ring atoms. It is more preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
Examples of the aryl group include a phenyl group, a biphenylyl group, a terphenylyl group, a biphenylenyl group, a naphthyl group, an acenaphthylenyl group, an anthryl group, a benzoanthryl group, an aceanthryl group, a phenanthryl group, a benzophenanthryl group, a phenalenyl group, Examples include fluorenyl group, pentacenyl group, picenyl group, pentaphenyl group, pyrenyl group, chrycenyl group, benzocricenyl group, s-indacenyl group, as-indacenyl group, fluoranthenyl group, and perylenyl group. Phenyl group, biphenylyl group , A terphenylyl group, and a naphthyl group are preferable, a phenyl group, a biphenylyl group, and a naphthyl group are more preferable, and a phenyl group and a p-, m-, or o-biphenylyl group are more preferable.

In the formula (2), R ¹¹ to R ¹⁴ are each independently a hydrogen atom or a substituent. In one embodiment of the present invention, R ¹¹ to R ¹⁴ are preferably hydrogen atoms. The substituents represented by R ¹¹ to R ¹⁴ are the same as the substituents described for R ¹ to R ¹⁰ .
Two adjacent groups selected from R ¹¹ to R ¹⁴ are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 18 ring carbon atoms, a substituted or unsubstituted ring forming carbon atom having 6 to 18 carbon atoms. Or a substituted or unsubstituted aliphatic heterocyclic ring having 5 to 18 ring atoms, or a substituted or unsubstituted aromatic heterocyclic ring having 6 ring atoms.
The substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 18 carbon atoms and the substituted or unsubstituted aliphatic heterocyclic ring having 5 to 18 ring atoms are as described for R ¹ to R ^10. is there.
Examples of the substituted or unsubstituted aromatic hydrocarbon ring having 6 to 18 carbon atoms include benzene, biphenylene, naphthalene, acenaphthylene, anthracene, benzoanthracene, aceanthrylene, phenanthrene, benzophenanthrene, phenalene, fluorene, and pyrene. , Chrysene, s-indacene, as-indacene, fluoranthene and the like.
Examples of the substituted or unsubstituted aromatic heterocyclic ring having 6 ring atoms include pyridine, pyrazine, pyridazine, pyrimidine, oxazine, and thiazine.
In one embodiment of the present invention, two adjacent groups selected from R ¹¹ to R ¹⁴ are not bonded to each other and thus do not need to form a ring.

In the formula (3), Y is O, S, NL ² —R ²⁵ , or CR ²⁶ R ²⁷ , preferably O, S, or NL ² —R ²⁵ .
In the present invention, a compound in which X in formula (2) is NL ² -R ²⁵ and Y in formula (3) is O, S, NL ² -R ²⁵ , or CR ²⁶ R ²⁷ is preferred. , X is ^N-L 2 ^{-R 25} of formula (2), Y is O, S, or more preferably a compound which is ^N-L 2 ^{-R 25} of formula (3), X in formula (2) There are ^N-L 2 ^{-R 25,} compound Y is ^N-L 2 ^{-R 25} of formula (3) is more preferable.

L ² is a single bond or a linking group. In one embodiment of the present invention, L ² is preferably a single bond, and in another embodiment, L ² is preferably a linking group.
The linking group represented by L ² has a substituted or unsubstituted ring-forming carbon number of 6 to 50, preferably 6 to 25, more preferably 6 to 18 arylene group or a substituted or unsubstituted ring forming atom number of 5 to 50, Preferably, it is a heteroarylene group having 5 to 24, more preferably 5 to 13, preferably a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, preferably 6 to 25, more preferably 6 to 18 carbon atoms. is there.
The arylene group is a divalent group obtained by removing one hydrogen atom from an aryl group having 6 to 50 ring carbon atoms described for R ¹ to R ¹⁰ , and the heteroarylene group is R ¹ to R 10. ^{And a} divalent group obtained by removing one hydrogen atom from an aromatic heterocyclic group having 5 to 50 ring atoms as described for No. 10.
L ² is preferably a phenylene group (including an isomer group), a biphenylene group (including an isomer group), and a terphenylene group (including an isomer group), more preferably a phenylene group (including an isomer group). ) And a biphenylene group (including an isomer group), more preferably an o-, m- or p-phenylene group.

R ²⁵ is a hydrogen atom or a substituent. In one embodiment of the present invention, R ²⁵ is preferably a hydrogen atom, and in another embodiment, R ²⁵ is preferably a substituent.
The substituent represented by R ²⁵ is the same as the substituents described for R ¹ to R ¹⁰ , preferably a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted ring carbon number of 6 to A substituted or unsubstituted aryl group having 7 to 51 carbon atoms having an aryl group having 6 to 50 ring carbon atoms; and a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 ring atoms. More preferably a group selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms and a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 ring atoms. It is a group selected more.
Examples of the substituted or unsubstituted aryl group include a phenyl group, a biphenylyl group (including an isomer group), a terphenylyl group (including an isomer group), a biphenylenyl group, a naphthyl group, an acenaphthylenyl group, an anthryl group, and a benzoan. Tolyl group, aceanthryl group, phenanthryl group, benzophenanthryl group, phenalenyl group, fluorenyl group, 9,9-dimethylfluorenyl group, pentacenyl group, picenyl group, pentaphenyl group, pyrenyl group, chrysenyl group, benzocrisenyl group , S-indacenyl group, as-indacenyl group, fluoranthenyl group and perylenyl group are preferable, phenyl group, biphenylyl group (including isomer group), terphenylyl group (including isomer group), 9,9-dimethyl Fluorenyl group and fluoranthenyl group are more preferred Properly, a phenyl group, p- biphenylyl group, m- biphenylyl group, p- terphenylyl group, 1-9,9- dimethyl fluorenyl group, and 3-fluoranthenyl group is more preferred.
Examples of the aromatic heterocyclic group include pyrrolyl group, furyl group, thienyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, imidazolyl group, oxazolyl group, thiazolyl group, pyrazolyl group, isoxazolyl group, Isothiazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, indolyl group, isoindolyl group, benzofuranyl group, isobenzofuranyl group, benzothiophenyl group (benzothienyl group, the same shall apply hereinafter), indolizinyl group, quinolidinyl group, quinolyl group, isoquinolyl Group, cinnolyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, indazolyl group, benzisoxazolyl group, benzisothiazolyl Group, dibenzofuranyl group, naphthobenzofuranyl group, dibenzothiophenyl group (dibenzothienyl group, the same applies hereinafter), naphthobenzothiophenyl group (naphthobenzothienyl group, the same applies hereinafter), carbazolyl group (N-carbazolyl group and C -Carbazolyl group, and so on), benzocarbazolyl group (benzo-N-carbazolyl group and benzo-C-carbazolyl group, so on), phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, A phenothiazinyl group, a phenoxazinyl group, and a xanthenyl group, and a dibenzofuranyl group, a dibenzothiophenyl group, and a carbazolyl group are preferable, a 2- or 4-dibenzofuranyl group, a 2- or 4-dibenzothiophenyl group, And an N-carbazolyl group is more preferable.
As the substituted aromatic heterocyclic group, the following groups are preferable.

R ²⁶ and R ²⁷ are each independently a hydrogen atom or a substituent. In one embodiment of the present invention, R ²⁶ and R ²⁷ are preferably a hydrogen atom, and in another embodiment, R ²⁶ and R ²⁷ are A substituent is preferred.
The substituents represented by R ²⁶ and R ²⁷ are the same as the substituents described with respect to R ¹ to R ¹⁰ , and in particular, an alkyl group having 1 to 50 carbon atoms, preferably 1 to 18 carbon atoms, more preferably 1 to 8 carbon atoms, An aryl group having 6 to 50 ring carbon atoms, preferably 6 to 25, more preferably 6 to 18 is preferable, and a methyl group, an ethyl group, or a phenyl group is more preferable.
R ²⁶ and R ²⁷ are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 18 ring carbon atoms or a substituted or unsubstituted aliphatic heterocyclic ring having 5 to 18 ring atoms. It may be formed. Examples of the aliphatic hydrocarbon ring include cyclopentane, cyclohexane and the like, and examples of the aliphatic heterocycle include imidazolidine, imidazoline, oxazolidine, dioxolane, thiazoline, tetrahydropyran, piperazine, piperidine, pyrazoline, Examples include pyrazolidine, pyrrolidine, pyrroline, tetrahydrofuran, tetrahydrothiophene, morpholine and the like.

R ²¹ to R ²⁴ are each independently a hydrogen atom or a substituent. In one embodiment of the present invention, R ²¹ to R ²⁴ are preferably hydrogen atoms. The substituents represented by R ²¹ to R ²⁴ are the same as the substituents described for R ¹ to R ¹⁰ .
Two adjacent groups selected from R ²¹ to R ²⁴ are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 18 ring carbon atoms, a substituted or unsubstituted ring forming carbon atom having 6 to 18 carbon atoms. Or a substituted or unsubstituted aliphatic heterocyclic ring having 5 to 18 ring atoms, or a substituted or unsubstituted aromatic heterocyclic ring having 6 ring atoms.
The aliphatic hydrocarbon ring having 5 to 18 ring carbon atoms, the aromatic hydrocarbon ring having 6 to 18 ring carbon atoms, the aliphatic heterocyclic ring having 5 to 18 ring atoms, and the number of ring forming atoms The aromatic heterocycle of 6 is as described for R ¹¹ to R ¹⁴ .
In one embodiment of the present invention, two adjacent groups selected from R ²¹ to R ²⁴ are not bonded to each other and thus do not need to form a ring.

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

The compound (1) is useful as a material for an organic EL device. The method for producing the compound (1) is not particularly limited, and those skilled in the art can easily produce the compound (1) by utilizing and changing known synthetic reactions with reference to the examples described below.

Organic EL Element Material The organic EL element material of the present invention contains the compound represented by the formula (1) (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 element of the present invention is useful as a material for producing an organic EL element. For example, it is used as a host material and a dopant material in a light emitting layer of a fluorescent light emitting unit or a host material in a light emitting layer of a phosphorescent light emitting unit. Can do. In addition, in both the fluorescent light emitting unit and the phosphorescent light emitting unit, it is also useful as a material for the anode-side organic thin film layer such as a hole transport layer, a hole injection layer, and an electron blocking layer provided between the anode and the light emitting layer. In addition, it is also useful as a material for cathode-side organic thin film layers such as an electron transport layer, an electron injection layer, and a hole blocking layer provided between the cathode and the light emitting layer.
In one embodiment of the present invention, the material for an organic EL device of the present invention is preferably used for a phosphorescent light emitting unit, and is preferably used as a host material in a light emitting layer of the phosphorescent light emitting unit.

Organic EL Element Next, the organic EL element of the present invention will be described.
An organic EL element has an organic thin film layer including one or more layers between a cathode and an anode. The organic thin film layer includes a light emitting layer, and at least one of the organic thin film layers includes the compound (1).
Examples of the organic thin film layer containing the compound (1) include an anode-side organic thin film layer (hole transport layer, hole injection layer, electron blocking layer, exciton blocking layer) provided between the anode and the light emitting layer. Etc.), light emitting layer, space layer, cathode side organic thin film layer (electron transport layer, electron injection layer, hole blocking layer, etc.), etc., but are not limited thereto. For example, it can be used as a host material, a dopant material, a hole injection layer material, or a hole transport layer material in the light emitting layer of the fluorescent light emitting unit. Further, it can be used as a host material, a hole injection layer material, and a hole transport layer material in a light emitting layer of a phosphorescent light emitting unit. It is used as a host material in the light emitting layer of a phosphorescent light emitting unit (red or green phosphorescent light emitting device).

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

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, the light emitting unit is generated by a phosphorescent light emitting layer between the light emitting layers. In order to prevent the excitons from diffusing into the fluorescent light emitting layer, a space layer may be provided. A typical layer structure of the 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)
(B) (hole injection layer /) hole transport layer / phosphorescent layer (/ electron transport layer)
(C) (hole injection layer /) hole transport layer / first fluorescent light emitting layer / second fluorescent light emitting layer (/ electron transport layer)
(D) (hole injection layer /) hole transport layer / first phosphorescent light emitting layer / second phosphorescent light emitting layer (/ electron transport layer)
(E) (hole injection layer /) hole transport layer / phosphorescent layer / space layer / fluorescent layer (/ electron transport 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)
(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)
(H) (hole injection layer /) hole transport layer / phosphorescent layer / space layer / first fluorescence layer / second fluorescence layer (/ electron transport layer)
(I) (hole injection layer /) hole transport layer / electron blocking layer / fluorescent light emitting layer (/ electron transport layer)
(J) (hole injection layer /) hole transport layer / electron blocking layer / phosphorescent layer (/ electron transport layer)
(K) (hole injection layer /) hole transport layer / exciton blocking layer / fluorescent light emitting layer (/ electron transport layer)
(L) (hole injection layer /) hole transport layer / exciton blocking layer / phosphorescent layer (/ electron transport layer)
(M) (hole injection layer /) first hole transport layer / second hole transport layer / fluorescent light emitting layer (/ electron transport layer)
(N) (hole injection layer /) first hole transport layer / second hole transport layer / phosphorescent layer (/ electron transport layer)
(O) (hole injection layer /) hole transport layer / fluorescent light emitting layer / hole blocking layer (/ electron transport layer)
(P) (hole injection layer /) hole transport layer / phosphorescent layer / hole blocking layer (/ electron transport layer)
(Q) (hole injection layer /) hole transport layer / fluorescent light emitting layer / triplet blocking layer (/ electron transport layer)
(R) (hole injection layer /) hole transport layer / phosphorescent layer / triplet blocking layer (/ electron transport layer)

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

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

FIG. 1 shows a schematic configuration of an example of the organic EL element. The organic EL element 1 includes a substrate 2, an anode 3, a cathode 4, and a light emitting unit 10 disposed between the anode 3 and the cathode 4. The light emitting unit 10 has at least one light emitting layer 5. Hole injection / transport layer 6 (anode-side organic thin film layer) between the light-emitting layer 5 and the anode 3, electron injection / transport layer 7 (cathode-side organic thin film layer) between the light-emitting layer 5 and the cathode 4, etc. May be formed. In addition, an electron barrier layer (not shown) may be provided on the anode 3 side of the light emitting layer 5, and a hole barrier layer (not shown) may be provided on the cathode 4 side of the light emitting layer 5. Thereby, electrons and holes can be confined in the light emitting layer 5, and the exciton generation probability in the light emitting layer 5 can be 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 organic EL element. As the substrate, for example, a plate made of glass, quartz, plastic, or the like can be used. Further, a flexible substrate may be used. The flexible substrate is a substrate that can be bent (flexible), and examples thereof include plastic substrates made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. . Moreover, an inorganic vapor deposition film can also be used.

Anode As the anode formed on the substrate, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a high work function (specifically, 4.0 eV or more). Specifically, for example, indium tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide, Examples include graphene. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium ( Pd), titanium (Ti), or a nitride of the metal (for example, titanium nitride).

These materials are usually formed by sputtering. For example, indium oxide-zinc oxide is a target in which 1 to 10 wt% of zinc oxide is added to indium oxide, and indium oxide containing tungsten oxide and zinc oxide is 0.5 to 5 wt. % And a target containing 0.1 to 1 wt% of zinc oxide can be formed by a sputtering method. In addition, you may produce by the vacuum evaporation method, the apply | coating method, the inkjet method, a spin coat method, etc.

The hole injection layer formed in contact with the anode is formed using a material that is easy to inject holes regardless of the work function of the anode. Therefore, a material generally used as an electrode material (for example, metal , Alloys, electrically conductive compounds, and mixtures thereof, elements belonging to Group 1 or Group 2 of the Periodic Table of Elements) can be used.
An element belonging to Group 1 or Group 2 of the periodic table, which is a material having a low work function, that is, an alkali metal such as lithium (Li) or cesium (Cs), and magnesium (Mg), calcium (Ca), or strontium Alkaline earth metals such as (Sr), and alloys containing these (eg, MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these can also be used. Note that when an anode is formed using an alkali metal, an alkaline earth metal, and an alloy containing these, 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 Injecting Layer The hole injecting layer is a layer containing a material having a high hole injecting property (hole injecting material). The compound (1) may be used alone or in combination with the following materials for the hole injection layer.

As hole injecting materials other than the compound (1), molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, Silver oxide, tungsten oxide, manganese oxide, or the like can be used.

4,4 ′, 4 ″ -tris (N, N-diphenylamino) triphenylamine (abbreviation: TDATA), 4,4 ′, 4 ″ -tris [N- (3- Methylphenyl) -N-phenylamino] triphenylamine (abbreviation: MTDATA), 4,4′-bis [N- (4-diphenylaminophenyl) -N-phenylamino] biphenyl (abbreviation: DPAB), 4,4 '-Bis (N- {4- [N'-(3-methylphenyl) -N'-phenylamino] phenyl} -N-phenylamino) biphenyl (abbreviation: DNTPD), 1,3,5-tris [N -(4-Diphenylaminophenyl) -N-phenylamino] benzene (abbreviation: DPA3B), 3- [N- (9-phenylcarbazol-3-yl) -N-phenylamino] -9- 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-injecting layer material.

Polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used. For example, poly (N-vinylcarbazole) (abbreviation: PVK), poly (4-vinyltriphenylamine) (abbreviation: PVTPA), poly [N- (4- {N ′-[4- (4-diphenylamino)] Phenyl] phenyl-N′-phenylamino} phenyl) methacrylamide] (abbreviation: PTPDMA), poly [N, N′-bis (4-butylphenyl) -N, N′-bis (phenyl) benzidine] (abbreviation: High molecular compounds such as Poly-TPD). In addition, a polymer compound to which an acid such as poly (3,4-ethylenedioxythiophene) / poly (styrenesulfonic acid) (PEDOT / PSS), polyaniline / poly (styrenesulfonic acid) (PAni / PSS) is added is used. You can also.

Furthermore, it is also preferable to use an acceptor material such as a hexaazatriphenylene (HAT) compound represented by the following formula (K) in combination with the compound (1).

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

Hole Transport Layer The hole transport layer is a layer containing a material having a high hole transport property (hole transport material). You may use the said compound (1) for a positive hole transport layer individually or in combination with the following compound.

As a hole transporting material other than the compound (1), for example, an aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used. As the aromatic amine compound, for example, 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 [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.

The hole-transporting layer includes 4,4′-di (9-carbazolyl) biphenyl (abbreviation: CBP), 9- [4- (9-carbazolyl) phenyl] -10-phenylanthracene (abbreviation: CzPA), 9- Carbazole derivatives such as phenyl-3- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazole (abbreviation: PCzPA) and 2-t-butyl-9,10-di (2-naphthyl) anthracene An anthracene derivative such as (abbreviation: t-BuDNA), 9,10-di (2-naphthyl) anthracene (abbreviation: DNA), 9,10-diphenylanthracene (abbreviation: DPAnth) may be used. A high molecular compound such as poly (N-vinylcarbazole) (abbreviation: PVK) or poly (4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.
However, compounds other than those described above may be used as long as they have higher hole transportability than electron transportability. Note that the layer including a compound having a high hole-transport property may be a single layer or a stacked layer including two or more layers including the above compound. For example, the hole transport layer may have a two-layer structure of 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 either the first hole transport layer or the second hole transport layer. In one embodiment of the present invention, the compound (1) is preferably contained in the first hole transport layer, and in another embodiment, the compound (1) is contained in the second hole transport layer. preferable.

The dopant material of a light emitting layer A light emitting layer is a layer containing material (dopant material) with high luminescent property, A various material can be used. For example, a fluorescent material or 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 that can be used for the light emitting layer, pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, and the like can be used. Specifically, N, N′-bis [4- (9H-carbazol-9-yl) phenyl] -N, N′-diphenylstilbene-4,4′-diamine (abbreviation: YGA2S), 4- (9H -Carbazol-9-yl) -4 '-(10-phenyl-9-anthryl) triphenylamine (abbreviation: YGAPA), 4- (10-phenyl-9-anthryl) -4'-(9-phenyl-9H -Carbazol-3-yl) triphenylamine (abbreviation: PCBAPA) and the like.

An aromatic amine derivative or the like can be used as a green fluorescent material that can be used for the light emitting layer. Specifically, N- (9,10-diphenyl-2-anthryl) -N, 9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCAPA), N- [9,10-bis (1,1 '-Biphenyl-2-yl) -2-anthryl] -N, 9-diphenyl-9H-carbazol-3-amine (abbreviation: 2PCABPhA), N- (9,10-diphenyl-2-anthryl) -N, N ', N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N- [9,10-bis (1,1'-biphenyl-2-yl) -2-anthryl] -N, N' , N′-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), N- [9,10-bis (1,1′-biphenyl-2-yl)]-N- [4- (9H-carbazole) -9-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 and the like can be used as red fluorescent materials that can be used for the light emitting layer. Specifically, N, N, N ′, N′-tetrakis (4-methylphenyl) tetracene-5,11-diamine (abbreviation: p-mPhTD), 7,14-diphenyl-N, N, N ′, And N′-tetrakis (4-methylphenyl) acenaphtho [1,2-a] fluoranthene-3,10-diamine (abbreviation: p-mPhAFD).

As a blue phosphorescent material that can be used for the light emitting layer, a metal complex such as an iridium complex, an osmium complex, or a platinum complex is used. Specifically, bis [2- (4 ′, 6′-difluorophenyl) pyridinato-N, C2 ′] iridium (III) tetrakis (1-pyrazolyl) borate (abbreviation: FIr6), bis [2- (4 ′ , 6′-difluorophenyl) pyridinato-N, C2 ′] iridium (III) picolinate (abbreviation: FIrpic), bis [2- (3 ′, 5′bistrifluoromethylphenyl) pyridinato-N, C2 ′] iridium (III ) Picolinate (abbreviation: Ir (CF3ppy) 2 (pic)), bis [2- (4 ′, 6′-difluorophenyl) pyridinato-N, C2 ′] iridium (III) acetylacetonate (abbreviation: FIracac) Can be mentioned.

An iridium complex or the like is used as a green phosphorescent material that can be used for the light emitting layer. Tris (2-phenylpyridinato-N, C2 ′) iridium (III) (abbreviation: Ir (ppy) 3), bis (2-phenylpyridinato-N, C2 ′) iridium (III) acetylacetonate ( Abbreviations: Ir (ppy) 2 (acac)), bis (1,2-diphenyl-1H-benzimidazolato) iridium (III) acetylacetonate (abbreviation: Ir (pbi) 2 (acac)), bis (benzo [ h] quinolinato) iridium (III) acetylacetonate (abbreviation: Ir (bzq) 2 (acac)) and the like.

As the red phosphorescent light-emitting material that can be used for the light-emitting layer, metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are 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.

Tris (acetylacetonato) (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 ( A rare earth metal complex such as TTA) 3 (Phen)) emits light from a rare earth metal ion (electron transition between different multiplicity), and thus can be used as a phosphorescent material.

Host Material of Light-Emitting Layer The light-emitting layer may have a configuration in which the above-described dopant material is dispersed in another material (host material). As the host material, the compound (1) of the present invention is preferable, and various other materials can be used. The lowest unoccupied orbital level (LUMO level) is higher than that of the dopant material, and the highest occupied orbital level (HOMO level). It is preferable to use a material having a low order.

Examples of the host material that can be used in combination with the compound (1) of the present invention include (1) a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex,
(2) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives,
(3) condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives;
(4) An aromatic amine compound such as a triarylamine derivative or a condensed polycyclic aromatic amine derivative is used.

For example, 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), etc. ;
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 ( Abbreviations: BPhen), heterocyclic compounds such as bathocuproin (abbreviation: BCP);
9- [4- (10-phenyl-9-anthryl) phenyl] -9H-carbazole (abbreviation: CzPA), 3,6-diphenyl-9- [4- (10-phenyl-9-anthryl) phenyl] -9H -Carbazole (abbreviation: DPCzPA), 9,10-bis (3,5-diphenylphenyl) anthracene (abbreviation: DPPA), 9,10-di (2-naphthyl) anthracene (abbreviation: DNA), 2-tert-butyl -9,10-di (2-naphthyl) anthracene (abbreviation: t-BuDNA), 9,9'-bianthryl (abbreviation: BANT), 9,9 '-(stilbene-3,3'-diyl) diphenanthrene ( Abbreviation: DPNS), 9,9 ′-(stilbene-4,4′-diyl) diphenanthrene (abbreviation: DPNS2), 3,3 ′, 3 ″-(benzene-1,3,5- Lily) tripyrene (abbreviation: TPB3), 9,10-diphenylanthracene (abbreviation: DPAnth), condensed aromatic compounds such as 6,12-dimethoxy-5,11-diphenylchrysene; and 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, 0-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 [N- (spiro-9,9 ' An aromatic amine compound such as -bifluoren-2-yl) -N-phenylamino] biphenyl (abbreviation: BSPB) can be used. 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). The compound (1) may be used alone or in combination with the following materials for the electron transport layer. For the electron transport layer, for example,
(1) Metal complexes such as aluminum complexes, beryllium complexes, zinc complexes,
(2) heteroaromatic 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 materials are mainly materials 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 two or more layers made of the above materials may be stacked.

Electron injection layer The electron injection layer is a layer containing a material having a high electron injection property. For the electron injection layer, lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), lithium oxide (LiOx), etc. Alkali metals, alkaline earth metals, or compounds thereof can be used. In addition, a material containing an electron transporting material containing an alkali metal, an alkaline earth metal, or a compound thereof, specifically, a material containing magnesium (Mg) in Alq may be used. In this case, electron injection from the cathode can be performed more efficiently.
Alternatively, a composite material obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer. Such a composite material has an excellent electron injecting property and electron transporting property because the organic compound receives electrons from the electron donor. In this case, the organic compound is preferably a material excellent in transporting received electrons. Specifically, for example, a material (metal complex, heteroaromatic compound, or the like) constituting the above-described electron transport layer is used. be able to. The electron donor may be any material that exhibits an electron donating property with respect to the organic compound. Specifically, 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 It is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a low work function (specifically, 3.8 eV or less) for the cathode. Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table of elements, that is, alkali metals such as lithium (Li) and cesium (Cs), and magnesium (Mg) and calcium (Ca ), Alkaline earth metals such as strontium (Sr), and alloys containing these (for example, rare earth metals such as MgAg, AlLi), europium (Eu), ytterbium (Yb), and alloys containing these.
Note that in the case where the cathode is formed using an alkali metal, an alkaline earth metal, or an alloy containing these, a vacuum evaporation method or a sputtering method can be used. Moreover, when using a silver paste etc., 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, an insulating layer made of an insulating thin film 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 or laminate of these 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, a material having both electron transport properties and hole transport properties is preferable. In order to prevent diffusion of triplet energy in the adjacent phosphorescent light emitting layer, the triplet energy is preferably 2.6 eV or more. Examples of the material used for the space layer include the same materials as those used for the above-described hole transport layer.

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 surrounding layers and confining the excitons in the light emitting layer. The compound (1) of the present invention is also suitable as a material for the electron blocking layer and the triplet blocking 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, a vacuum deposition method, a molecular beam deposition method (MBE method) or the like, or a dipping method, a spin coating method, a casting method, a bar coating method, a roll coating method, etc. using a solution of a compound that forms a layer. It can form by the well-known method by the apply | coating method.

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, and conversely, if it is too thick, a high driving voltage is required and the efficiency is lowered, so it is usually 5 nm to 10 μm. 10 nm to 0.2 μm is more preferable.

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.

Synthesis Example 1 (Synthesis of Compound (1))
Compound (1) was synthesized as follows.

In a 500 ml three-necked flask under a nitrogen atmosphere, 2,6-dibromobenzaldehyde (14.5 g, 54.9 mmol), 9-phenyl-4- (4,4,5,5-tetramethyl-1,3-dioxaborolane- 2-yl) carbazole (15.1 g, 40.9 mmol), Pd (PPh ₃ ) ₄ (3.17 g, 2.75 mmol), 2M sodium carbonate aqueous solution (60 ml), 1,2-dimethoxyethane (120 ml) were added. The mixture was heated and stirred at 100 ° C. The organic layer was extracted with dichloromethane, the obtained organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain a black crude product. Purification by silica gel chromatography gave 9.10 g of white compound (1-a). (Yield 52%)

Under a nitrogen atmosphere, (methoxymethyl) triphenylphosphonium chloride (14.6 g, 42.6 mmol) and THF (120 ml) were placed in a 500 ml three-necked flask, and the reactor was cooled to 0 ° C. To this, potassium tertiary butoxide (4.30 g, 38.3 mmol) was slowly added, and the mixture was further stirred at 0 ° C. After 30 minutes, a THF solution (20 ml) of compound (1-a) (9.10 g, 21.3 mmol) was added dropwise at 0 ° C. After completion of the addition, the reactor was heated and stirred at 50 ° C. After 5 hours, the reaction was cooled to room temperature and water (120 ml) was added. The organic layer was extracted with dichloromethane, the obtained organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain an orange crude product. Purification by silica gel chromatography gave 9.28 g of pale yellow compound (1-b). (Yield 96%)

Compound (1-b) (9.25 g, 20.4 mmol) and dichloromethane (200 ml) were placed in a 500 ml flask, and the reactor was cooled to 0 ° C. To this was slowly added methanesulfonic acid (1.32 ml, 20.4 mmol) and stirred at room temperature. After 3 hours, water (200 ml) was added, the organic layer was extracted with dichloromethane, the obtained organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain a white crude product. Purification by silica gel chromatography gave 7.88 g of white compound (1-c). (Yield 91%)

Under a nitrogen atmosphere, compound (1-c) (7.88 g, 18.7 mmol), bispinacolate diboron (7.12 g, 28.1 mmol), Pd (dppf) Cl ₂ (1. 53 g, 1.87 mmol), potassium acetate (5.51 g, 56.1 mmol), and dimethyl sulfoxide (28 ml) were added, and the mixture was heated and stirred at 80 ° C. After 8 hours, the reaction solution was filtered through Celite, and the solvent of the filtrate was distilled off under reduced pressure to obtain a black crude product. Purification by silica gel column chromatography gave 6.86 g of white compound (1-d). (Yield 78%)

In a 500 ml three-necked flask under a nitrogen atmosphere, compound (1-d) (6.86 g, 14.6 mmol), 2-iodonitrobenzene (4.36 g, 17.5 mmol), Pd (PPh ₃ ) ₄ (0.843 g) , 0.73 mmol), 2M aqueous sodium carbonate solution (22 ml) and 1,2-dimethoxyethane (44 ml) were added, and the mixture was heated and stirred at 100 ° C. After 6 hours, the reaction solution was filtered through Celite, and the solvent of the filtrate was distilled off under reduced pressure to obtain a black crude product. Purification by silica gel column chromatography gave 4.65 g of yellow compound (1-e). (Yield 69%)

In a nitrogen atmosphere, put the compound (1-e) (4.65 g, 10.0 mmol), triphenylphosphine (6.56 g, 25.0 mmol), 1,2-dichlorobenzene (50 ml) in a 500 ml three-necked flask. The mixture was heated and stirred at 190 ° C. After 5 hours, the reaction solution was cooled to room temperature, and dichlorobenzene was distilled off under reduced pressure to obtain a black crude product. Purification by silica gel chromatography gave 2.83 g of white compound (1-f). (Yield 65%)

In a 500 ml three-necked flask under a nitrogen atmosphere, compound (1-f) (2.10 g, 4.86 mmol), 2-chloro-4-phenylquinazoline (1.64 g, 6.80 mmol), Pd ₂ (dba) ₃ (0.223 g, 0.243 mmol), x-Phos (0.463 g, 0.972 mmol), sodium tertiary butoxide (0.701 g, 7.29 mmol) and xylene (24 ml) were added, and the mixture was heated and stirred at 120 ° C. . After 6 hours, the reaction solution was filtered, and the filtrate was washed with methanol, water, and toluene, and then the solvent was distilled off under reduced pressure to obtain 2.80 g of yellow compound (1). (Yield 90%)

Synthesis Example 2 (Synthesis of Compound (2))
Compound (2) was synthesized as follows.

In a 500 ml three-necked flask under nitrogen atmosphere, 2-bromo-6-chlorobenzaldehyde (30.4 g, 139 mmol), 4-dibenzothiopheneboronic acid (316 g, 139 mmol), Pd (PPh ₃ ) ₄ (3.21 g, 2 .78 mmol), 2M aqueous sodium carbonate solution (140 ml) and 1,2-dimethoxyethane (620 ml) were added, and the mixture was heated and stirred at 100 ° C. After 8 hours, the reaction solution was filtered through Celite, and the solvent of the filtrate was distilled off under reduced pressure to obtain a black crude product. Purification by silica gel column chromatography gave 37.4 g of white compound (2-a). (Yield 82%)

Under a nitrogen atmosphere, (methoxymethyl) triphenylphosphonium chloride (48.1 g, 140 mmol) and toluene (500 ml) were placed in a 500 ml three-necked flask and the reactor was cooled to 0 ° C. To this, potassium tertiary butoxide (15.8 g, 140 mmol) was slowly added, and the mixture was further stirred at 0 ° C. After 30 minutes, a toluene solution (250 ml) of compound (2-a) (30.2 g, 93.6 mmol) was added dropwise at 0 ° C. After completion of the addition, the reactor was heated and stirred at 80 ° C. After 5 hours, the reaction was cooled to room temperature and water (500 ml) was added. The organic layer was extracted with dichloromethane, the obtained organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain an orange crude product. Purification by silica gel chromatography gave 27.5 g of pale yellow compound (2-b). (Yield 84%)

Compound (2-b) (27.5 g, 78.4 mmol) and chloroform (350 ml) were placed in a 500 ml flask, and the reactor was cooled to 0 ° C. To this, methanesulfonic acid (5.08 ml, 78.4 mmol) was slowly added and stirred at room temperature. Three hours later, water (150 ml) was added, the organic layer was extracted with dichloromethane, the obtained organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain a white crude product. Purification by silica gel chromatography gave 11 g of white compound (2-c). (Yield 44%)

In a 500 ml three-necked flask under a nitrogen atmosphere, compound (2-c) (6.38 g, 20.0 mmol), bispinacolate diboron (10.2 g, 40.0 mmol), Pd ₂ (dba) ₃ (0. 183 g, 0.200 mmol), X-Phos (0.381 g, 0.800 mmol), potassium acetate (5.89 g, 60.0 mmol) and 1,4-dioxane (200 ml) were added, and the mixture was heated and stirred at 90 ° C. After 8 hours, the reaction solution was filtered through Celite, and the solvent of the filtrate was distilled off under reduced pressure to obtain a black crude product. Purification by silica gel column chromatography gave 3.55 g of white compound (2-d). (Yield 42%)

Under a nitrogen atmosphere, compound (2-d) (2.05 g, 5.00 mmol), 2-iodonitrobenzene (2.74 g, 11.0 mmol), Pd (PPh ₃ ) ₄ (0.578 g) was added to a 500 ml three-necked flask. , 0.500 mmol), 2M aqueous sodium carbonate solution (7.5 ml) and 1,2-dimethoxyethane (17 ml) were added, and the mixture was heated and stirred at 100 ° C. After 30 hours, the reaction solution was filtered through Celite, and the solvent of the filtrate was distilled off under reduced pressure to obtain a black crude product. Purification by silica gel column chromatography gave 1.30 g of yellow compound (2-e). (Yield 63%)

In a nitrogen atmosphere, put the compound (2-e) (1.29 g, 3.18 mmol), triphenylphosphine (2.09 g, 7.95 mmol), and 1,2-dichlorobenzene (12 ml) in a 500 ml three-necked flask. The mixture was heated and stirred at 190 ° C. After 5 hours, the reaction solution was cooled to room temperature, and dichlorobenzene was distilled off under reduced pressure to obtain a black crude product. Purification by silica gel chromatography gave 0.79 g of white compound (2-f). (Yield 62%)

In a 500 ml three-necked flask under a nitrogen atmosphere, compound (2-g) (0.79 g, 2.12 mmol), 2-chloro-4-phenylquinazoline (1.02 g, 4.23 mmol), cesium carbonate (0.827 g) , 2.54 mmol) and N, N-dimethylformamide (30 ml) were added, and the mixture was stirred with heating at 120 ° C. After 6 hours, the reaction solution was filtered, the filtrate was washed with methanol, water and dichloromethane, and then the solvent was distilled off under reduced pressure to obtain 0.98 g of yellow compound (2). (Yield 80%)

Synthesis Example 3 (Synthesis of Compound (3))
Compound (3) was synthesized as follows.

6-Fluoranthranilic acid (35.0 g, 225 mmol), water (885 ml) and acetic acid (26 ml) were placed in a 2000 ml flask and stirred at 35 ° C. for 15 minutes. The aqueous solution which melt | dissolved sodium cyanate (36.7g, 564mmol) in water (442ml) was dripped here, and the reaction liquid was stirred at 35 degreeC for 30 minutes. Sodium hydroxide (180 g, 4.51 mmol) was then slowly added and the reactor was cooled to room temperature. Dilute hydrochloric acid (374 ml) was added to the reactor, filtration was performed, and the filtrate was washed with water. The obtained solid was dried to obtain 37.2 g of a white compound (3-a). (Yield 92%)

A 200 ml flask was charged with (3-a) (2.6 g, 14.4 mmol) and toluene (29 ml) and heated to 50 ° C. Phosphoryl chloride (9.88 ml, 108 mmol) was added dropwise thereto, followed by dropwise addition of diazabicycloundecene (4.3 ml, 28.9 mmol). The reaction was heated and stirred at 120 ° C. for 12 hours, then cooled to room temperature, and the reaction was slowly added to ice water. The organic layer was extracted with ethyl acetate, and the resulting organic layer was washed with brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude product. Purification by silica gel chromatography gave 3.41 g of white compound (3-b). (Yield 81%)

Under a nitrogen atmosphere, compound (3-b) (2.17 g, 10.0 mmol), 2-hydroxybenzeneboronic acid (1.38 g, 10.0 mmol), Pd (OAc) ₂ (0. 225 g, 1.00 mmol), P (t-Bu) ₃ HBF ₄ (0.290 g, 1.00 mmol), potassium fluoride (1.74 g, 30.0 mmol) and tetrahydrofuran (10 ml) were added and stirred at room temperature. . After 1.5 hours, anhydrous magnesium sulfate was added to the reaction solution, and this was filtered through Celite to obtain a crude product. Purification by silica gel column chromatography gave 2.27 g of pale yellow compound (3-c). (Yield 96%)

Compound (3-c) (3.02 g, 11.0 mmol), potassium carbonate (1.67 g, 12.1 mmol), N, N-dimethylformamide (55 ml) was placed in a 500 ml three-necked flask and stirred at room temperature. . After 5 minutes, water (100 ml) was added to the reaction solution, the precipitated solid was filtered, the filtrate was washed with water, and the solvent was distilled off under reduced pressure to remove the yellow compound (3-d) by 2. 60 g was obtained. (Yield 93%)

In a 500 ml three-necked flask under a nitrogen atmosphere, compound (2-g) (1.13 g, 3.03 mmol), compound (3-d) (1.54 g, 6.06 mmol), cesium carbonate (1.19 g, 3 .64 mmol) and N, N-dimethylformamide (30 ml) were added, and the mixture was heated and stirred at 120 ° C. After 6 hours, the reaction solution was filtered, the filtrate was washed with methanol, water, and toluene, and then the solvent was distilled off under reduced pressure to obtain 1.37 g of yellow compound (3). (Yield 75%)

Synthesis Example 4 (Synthesis of Compound (4))
Compound (4) was synthesized as follows.

In a 500 ml three-necked flask under an argon atmosphere, compound (1-f) (2.38 g, 5.50 mmol), compound (3-d) (1.54 g, 6.05 mmol), Pd ₂ (dba) ₃ (0 151 g, 0.165 mmol), xanthophos (0.191 g, 0.33 mmol), sodium tertiary butoxide (0.81 g, 8.25 mmol) and toluene (100 ml) were added and heated to reflux. After 2 hours, the reaction solution was filtered, and the filtrate was washed with methanol, water, and toluene, the solvent was distilled off under reduced pressure, and recrystallization was carried out using chlorobenzene, whereby 2. yellow compound (4) was obtained. 53 g was obtained. (Yield 70%)

Synthesis Example 5 (Synthesis of Compound (5))
Compound (5) was synthesized as follows.

In a 500 ml three-necked flask under an argon atmosphere, compound (1-f) (2.59 g, 6.00 mmol), 8-chlorofluoranthene (1.56 g, 6.60 mmol), Pd ₂ (dba) ₃ (0 .165 g, 0.18 mmol), xanthophos (0.208 g, 0.36 mmol), sodium tertiary butoxide (0.88 g, 9.00 mmol), and xylene (100 ml) were added and heated to reflux for 15 hours. After returning to room temperature, 100 mL of water was added and extracted with toluene. The collected organic layer was washed with water and saturated brine, and dried over sodium sulfate. After sodium sulfate was filtered off, the solution was concentrated. The obtained product was purified by silica gel column chromatography to obtain 3.28 g of yellow compound (5). (Yield 86%)

Synthesis Example 6 (Synthesis of Compound (6))
Compound (6) was synthesized as follows.

In a 500 ml three-necked flask under an argon atmosphere, compound (1-c) (9.66 g, 22.87 mmol), 2-chloroaniline (2.92 g, 22.87 mmol), Pd ₂ (dba) ₃ (2.09 g , 2.29 mmol), tritertiary butylphosphine-tetrafluoroborate (1.33 g, 4.57 mmol), sodium tertiary butoxide (0.88 g, 9.00 mmol), toluene (200 ml), and heated for 24 hours. Refluxed. After filtering the reaction mixture, the remaining solid was washed with ethyl acetate. Water was added to the filtrate and extracted with ethyl acetate. The collected organic layer was washed with water and saturated brine, and dried over sodium sulfate. After sodium sulfate was filtered off, the solution was concentrated. The obtained product was purified by silica gel column chromatography, and further purified by a Soxhlet extractor using a toluene solvent, to obtain 2.6 g of a white compound (6-a). (Yield 26%)

In an argon atmosphere, a compound (6-a) (1.3 g, 3.01 mmol), compound (3-d) (1.53 g, 6.01 mmol), Pd ₂ (dba) ₃ (0 0.06 g, 0.06 mmol), xanthophos (0.07 g, 0.12 mmol), sodium tertiary butoxide (0.40 g, 4.21 mmol), and toluene (50 ml) were added and heated to reflux. After 2 hours, 30 mL of toluene was distilled off and the residue was cooled with ice water. The precipitated solid was collected by filtration, washed with toluene, and dried. Then, after adding chlorobenzene and returning to room temperature, 100 mL of water was added and extracted using toluene. The collected organic layer was washed with water and saturated brine, and dried over sodium sulfate. After sodium sulfate was filtered off, the solution was concentrated. The obtained product was purified by silica gel column chromatography to obtain 1.64 g of yellow compound (6). (Yield 84%)

Synthesis Example 7 (Synthesis of Compound (7))
Compound (7) was synthesized as follows.

In a 250 ml three-necked flask under an argon atmosphere, compound (6-a) (1.3 g, 3.01 mmol), 2-bromofluoranthene (1.01 g, 3.61 mmol), Pd ₂ (dba) ₃ (0 0.06 g, 0.06 mmol), xanthophos (0.07 g, 0.12 mmol), sodium tertiary butoxide (0.40 g, 4.21 mmol), and toluene (50 ml) were added and heated to reflux. After 24 hours, the solid was filtered off and the filtrate was washed with water and dried using magnesium sulfate. After concentrating the solution, the resulting product was purified by silica gel column chromatography to obtain 1.15 g of yellow compound (7). (Yield 60%)

Synthesis Example 8 (Synthesis of Compound (8))
Compound (8) was synthesized as follows.

Under a nitrogen atmosphere, compound (1-f) (2.6 g, 6.00 mmol), 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (2 ^{_{_{.4g, 6.00mmol), Pd (P}}} t Bu 3) 2 (0.06g, 0.3mmol), sodium tertiary butoxide (1.2g, 12.6mmol), was placed toluene (60 ml), at 95 ° C. Stir for 6 hours. After the reaction solution was cooled to room temperature, the solid was collected by filtration and washed with toluene. The obtained product was purified by silica gel column chromatography to obtain 2.5 g of white compound (8). (Yield 53%)

Synthesis Example 9 (Synthesis of Compound (9))
Compound (9) was synthesized as follows.

Compound (1-f) (2.6 g, 6.00 mmol), 4- (4-bromophenyl) dibenzo [b, d] furan (2.0 g, 6.20 mmol) in a 250 ml three-necked flask under a nitrogen atmosphere , Pd (P ^t Bu ₃ ) ₂ (0.06 g, 0.3 mmol), sodium tertiary butoxide (1.2 g, 12.6 mmol) and toluene (60 ml) were added, and the mixture was stirred at 110 ° C. for 6 hours. After the reaction solution was cooled to room temperature, the solid was filtered off and the filtrate was concentrated. The obtained product was washed with methanol and purified by silica gel column chromatography to obtain 2.8 g of white compound (9). (Yield 70%)

Example 1
Manufacture of EL element A glass substrate with an ITO transparent electrode (manufactured by Geomatic Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 10 minutes, and then UV ozone cleaning was performed for 30 minutes. The thickness of the ITO transparent electrode was 120 nm.
The cleaned glass substrate with a transparent electrode was mounted on a substrate holder of a vacuum deposition apparatus, and the following acceptor material (Compound A) was first deposited so as to cover the transparent electrode to form an acceptor layer having a thickness of 5 nm. On this acceptor layer, the following aromatic amine compound (compound B) was vapor-deposited to form a 220 nm-thick hole transport layer.
Next, on the hole transport layer, the compound (1) obtained in Synthesis Example 1 and the following compound RD-1 were co-evaporated to form a co-deposited film having a thickness of 40 nm. The concentration of Compound RD-1 was 2.0% by mass. This co-deposited film functions as a light emitting layer.
And on this light emitting layer, the following compound C (50 mass%) and Liq (50 mass%) which is an electron donating dopant were binary-deposited, and the 25-nm-thick electron carrying layer was formed.
Next, Liq was vapor-deposited on the electron transport layer to form an electron injecting electrode (cathode) having a thickness of 1 nm.
And metal Al was vapor-deposited on this electron injecting electrode, the metal Al cathode with a film thickness of 80 nm was formed, and the organic EL element was manufactured.
Evaluation of organic EL element The produced organic EL element was made to emit light by direct current drive, and the drive voltage (V) at 10 mA / cm ² was determined. Further, an 80% lifetime at a current density of 50 mA / cm ² was determined. The 80% life means the time until the luminance is attenuated to 80% of the initial luminance in constant current driving. The results are shown in Table 1.

Comparative Examples 1 and 2
An organic EL device was produced in the same manner as in Example 1 except that the comparative compound (1) or (2) was used in place of the compound (1), and the driving voltage (V) was 80% as in Example 1. Lifespan was measured. The results are shown in Table 1.

The compound (1) corresponds to a compound obtained by crosslinking one carbazole structure benzene ring and the other carbazole structure benzene ring of the comparative compound (1). From Table 1, it can be seen that the organic EL device using the compound (1) has a lower driving voltage and longer life than the organic EL device using the comparative compound (1).
In addition, the EL device using the comparative compound (2) having a structure in which an indole ring is condensed at

positions

2 and 3 of the phenanthrene skeleton has a higher driving voltage and a longer life than the organic EL device using the compound (1). Is significantly shorter.

Reference Example A compound represented by the formula (2) or (3) was bonded to one or both of the 2-position and 3-position, and the 6-position and 7-position of the compounds (I) to (III) of the present invention and the phenanthrene ring. The triplet energy gap E _T1 (difference between the first excited triplet energy and the ground state) of the comparative compounds (i) to (v) is calculated using a quantum chemistry calculation program (Gaussian 03, Revision D.01, calculation level B3LYP / 6 -31 g *). The results are shown in Table 2.

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

Claims

The compound represented by Formula (1).

((Where
The broken lines indicate adjacent groups R 1 and R 2 included in A, adjacent groups R 3 and R 4 included in B, adjacent groups R 5 and R 6 included in C, and adjacent groups R 7 and R 8 included in D. , Each adjacent group selected from the adjacent groups R 9 and R 10 contained in E may or may not be bonded to the group represented by the formula (2) or (3);
The adjacent group contained in one selected from A to E is bonded to the group represented by the formula (2);
The adjacent groups contained in 1 to 4 groups selected from the remaining A to E are each independently bonded to the group represented by the formula (3);
When the adjacent group is bonded to the group represented by the formula (2), one of the adjacent groups is bonded to * 1, and the other is bonded to * 2.
When the adjacent group is bonded to the group represented by the formula (3), one of the adjacent groups is bonded to * 3, and the other is bonded to * 4.
R 1 to R 10 represent a bond bonded to * 1, * 2, * 3 or * 4 when bonded to a group represented by the formula (2) or (3);
R 1 to R 10 each independently represent a hydrogen atom or a substituent when not bonded to the group represented by the formula (2) or (3), and two adjacent groups are bonded to each other, A substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 18 carbon atoms, a substituted or unsubstituted aromatic heterocyclic ring having 5 to 18 ring atoms, or a substituted or unsubstituted ring atom having 5 to 18 ring atoms The aliphatic heterocyclic ring may be formed. However, it excludes when forming group represented by Formula (2) or (3). )

(In the formula (2),
X is O, S, or NL 1 -R 15 ;
L 1 is a single bond or a linking group;
R 15 is a hydrogen atom or a substituent,
R 11 to R 14 are each independently a hydrogen atom or a substituent, and adjacent two groups are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 18 ring carbon atoms, A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 18 carbon atoms, a substituted or unsubstituted aliphatic heterocyclic ring having 5 to 18 ring atoms, or a substituted or unsubstituted aromatic ring having 6 ring atoms A group heterocycle may be formed,
In formula (3),
Y is O, S, NL 2 -R 25 , or CR 26 R 27 ;
L 2 is a single bond or a linking group,
R 25 is a hydrogen atom or a substituent,
R 26 and R 27 are each independently a hydrogen atom or a substituent, and bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 18 ring carbon atoms or a substituted or unsubstituted ring. An aliphatic heterocyclic ring having 5 to 18 ring atoms may be formed,
R 21 to R 24 are each independently a hydrogen atom or a substituent, and adjacent two groups are bonded to each other to form a substituted or unsubstituted aliphatic hydrocarbon ring having 5 to 18 ring carbon atoms, A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 18 carbon atoms, a substituted or unsubstituted aliphatic heterocyclic ring having 5 to 18 ring atoms, or a substituted or unsubstituted aromatic ring having 6 ring atoms A group heterocycle may be formed. ))
The compound according to claim 1, which is represented by the following formula (10-1).

(In the formula, the curve indicated by a solid line shows that the adjacent group contained in one selected from A to E is bonded to the group represented by the formula (2), and the adjacent groups contained in the remaining four are And each independently represents a condensed ring bonded to the group represented by the formula (3).)
The compound according to claim 1, which is represented by the following formula (10-2).

(In the formula, the curve indicated by a solid line indicates that the adjacent group contained in one selected from A to C and D is bonded to the group represented by the formula (2) and the adjacent group contained in the remaining three. It represents that each group is independently bonded to the group represented by the formula (3) to form a condensed ring.)
The compound according to claim 1, which is represented by the following formula (10-6) or (10-7).

(In the curve shown by the solid line in the formula (10-6), the adjacent group contained in one selected from A, C and D is bonded to the group represented by the formula (2), and the remaining two Each of the adjacent groups contained is independently bonded to the group represented by the formula (3) to form a condensed ring;
In the curve shown by the solid line in the formula (10-7), the adjacent group contained in one selected from B, C and D is bonded to the group represented by the formula (2) and contained in the remaining two. The said adjacent group to be bonded | bonded respectively with the group represented by Formula (3) forms the condensed ring. )
The compound according to claim 1, which is represented by the following formula (10-11), (10-13), (10-14) or (10-16).

(The curve indicated by the solid line in the formula (10-11) shows that the adjacent group contained in one of C and D is bonded to the group represented by the formula (2), and the neighboring group contained in the other is represented by the formula (10). 3) represents a bond to the group represented by
In the curve shown by the solid line in Formula (10-13), the adjacent group contained in one of A and C is bonded to the group represented by Formula (2), and the adjacent group contained in the other is represented by Formula (3). ) To the group represented by
In the curve shown by the solid line in the formula (10-14), the adjacent group contained in one of B and C is bonded to the group represented by the formula (2), and the adjacent group contained in the other is represented by the formula (3 ) To the group represented by
In the curve shown by the solid line in Formula (10-16), the adjacent group contained in one of A and D is bonded to the group represented by Formula (2), and the adjacent group contained in the other is represented by Formula (3). ) Represents a bond to a group represented by
The compound according to claim 1, which is represented by the following formula (10-13), (10-14) or (10-16).

In the curve shown by the solid line in Formula (10-13), the adjacent group contained in one of A and C is bonded to the group represented by Formula (2), and the adjacent group contained in the other is represented by Formula (3). ) To the group represented by
In the curve shown by the solid line in the formula (10-14), the adjacent group contained in one of B and C is bonded to the group represented by the formula (2), and the adjacent group contained in the other is represented by the formula (3 ) To the group represented by
In the curve shown by the solid line in Formula (10-16), the adjacent group contained in one of A and D is bonded to the group represented by Formula (2), and the adjacent group contained in the other is represented by Formula (3). ) Represents a bond to a group represented by
The compound according to any one of claims 1 to 6, wherein the group represented by the formula (2) is bonded to the adjacent group contained in one selected from A to D.
The compound according to any one of claims 1 to 7, wherein the group represented by the formula (3) is bonded to the adjacent group contained in 1 to 3 groups selected from A to D.
The compound according to any one of claims 1 to 8, wherein the compound represented by the formula (1) is represented by the formula (20) or (30).

(Wherein R 1 to R 4 , R 7 to R 10 , R 11 to R 14 , and X are as described above, and a curve indicated by a broken line is a group selected from A, B, D, and E 1 to (It represents that the adjacent groups contained in each of the four are independently bonded to the group represented by the formula (3).)
The compound according to any one of claims 1 to 8, wherein the compound represented by the formula (1) is represented by any one of the formulas (40), (50) and (60).

(Where
R 1 to R 10 , R 11 to R 14 , and X are as described above,
In the formulas (40) and (50), the curve indicated by a broken line shows that each of the adjacent groups contained in 1 to 4 selected from A to C and E is independently represented by the formula (3). Represents a bond to the group
In the formula (60), the curve indicated by the broken line shows that the adjacent groups contained in each of 1 to 4 selected from A to D are independently bonded to the group represented by the formula (3). Represents that )
11. The adjacent group selected from R 1 to R 10 and not bonded to the group represented by the formula (2) or (3) does not bond to each other, and therefore does not form a ring. The compound according to item 1.
The compound according to any one of claims 1 to 11, wherein X is NL 1 -R 15 .
The compound according to any one of claims 1 to 12, wherein X is NL 1 -R 15 and Y is O, S, or NL 2 -R 25 .
The compound according to any one of claims 1 to 12, wherein X is NL 1 -R 15 and Y is CR 26 R 27 .
R 15 represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms; a substituted or unsubstituted ring forming carbon number 6 to 50 An aryl group having a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms and an aralkyl group having 7 to 51 carbon atoms; an amino group; an alkyl group having 1 to 50 carbon atoms and a ring carbon atom having 6 to 50 carbon atoms. A mono- or di-substituted amino group having a substituent selected from aryl groups; a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms; a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; A substituent selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; Mono-substituted, di-substituted or tri-substituted silyl groups; substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms; substituted or unsubstituted haloalkoxy groups having 1 to 50 carbon atoms; substituted or unsubstituted ring forming atoms The compound according to any one of claims 1 to 14, which is a group selected from the group consisting of 5 to 50 aromatic or non-aromatic heterocyclic group; halogen atom; cyano group; and nitro group.
R 15 represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; a substituted or unsubstituted ring group having 6 to 50 carbon atoms 16. The aralkyl group having 7 to 51 carbon atoms having an aryl group; and a group selected from the group consisting of a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 ring atoms. The compound according to item.
R 15 is a group selected from the group consisting of a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 ring atoms. The compound according to any one of claims 1 to 16.
R 25 represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms; a substituted or unsubstituted ring forming carbon number 6 to 50 An aryl group having a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms and an aralkyl group having 7 to 51 carbon atoms; an amino group; an alkyl group having 1 to 50 carbon atoms and a ring carbon atom having 6 to 50 carbon atoms. A mono- or di-substituted amino group having a substituent selected from aryl groups; a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms; a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; A substituent selected from a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms and a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; Mono-substituted, di-substituted or tri-substituted silyl groups; substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms; substituted or unsubstituted haloalkoxy groups having 1 to 50 carbon atoms; substituted or unsubstituted ring forming atoms The compound according to any one of claims 1 to 13, which is a group selected from the group consisting of 5 to 50 aromatic or non-aromatic heterocyclic group; halogen atom; cyano group; and nitro group.
R 25 represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms; a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms; a substituted or unsubstituted ring group having 6 to 50 carbon atoms The aralkyl group having 7 to 51 carbon atoms having an aryl group; and a group selected from the group consisting of a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 ring atoms. 2. The compound according to item 1.
R 25 is a group selected from the group consisting of a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 ring atoms. The compound according to any one of claims 1 to 13, 18 and 19.
R 26 and R 27 are each independently a hydrogen atom, an alkyl group having 1 to 50 carbon atoms; a cycloalkyl group having 3 to 50 ring carbon atoms; an aryl group having 6 to 50 ring carbon atoms; Mono-substituted having a substituent selected from an aryl group having 7 to 51 carbon atoms having 6 to 50 aryl groups; an amino group; an alkyl group having 1 to 50 carbon atoms and an aryl group having 6 to 50 ring carbon atoms; Di-substituted amino group; alkoxy group having an alkyl group having 1 to 50 carbon atoms; aryloxy group having an aryl group having 6 to 50 ring carbon atoms; alkyl group having 1 to 50 carbon atoms and 6 to 50 ring carbon atoms A mono-substituted, di-substituted or tri-substituted silyl group having a substituent selected from the following aryl groups; a haloalkyl group having 1 to 50 carbon atoms; a haloalkoxy group having 1 to 50 carbon atoms; and a ring atom number of 5 to 50 Aromatic or non-aromatic heterocyclic group, a halogen atom, a cyano group, and a compound according to any one of claims 1 to 12 and 14 is a group selected from the group consisting of nitro group.
The groups selected from R 1 to R 10 and not bonded to the group represented by formula (2) or (3) are each independently a hydrogen atom, an alkyl group having 1 to 50 carbon atoms; A cycloalkyl group having 3 to 50 carbon atoms; an aryl group having 6 to 50 ring carbon atoms; an aralkyl group having 7 to 51 carbon atoms having an aryl group having 6 to 50 ring carbon atoms; an amino group; A mono- or di-substituted amino group having a substituent selected from an alkyl group and an aryl group having 6 to 50 ring carbon atoms; an alkoxy group having an alkyl group having 1 to 50 carbon atoms; an aryl having 6 to 50 ring carbon atoms An aryloxy group having a group; a mono-, di- or tri-substituted silyl group having a substituent selected from an alkyl group having 1 to 50 carbon atoms and an aryl group having 6 to 50 ring carbon atoms; Haloalkyl A haloalkoxy group having 1 to 50 carbon atoms; an aromatic or non-aromatic heterocyclic group having 5 to 50 ring atoms; a halogen atom; a cyano group; and a nitro group. The compound according to any one of 1 to 21.
R 11 to R 14 and R 21 to R 24 are each independently a hydrogen atom, an alkyl group having 1 to 50 carbon atoms; a cycloalkyl group having 3 to 50 ring carbon atoms; An aryl group; an aryl group having 7 to 51 carbon atoms having an aryl group having 6 to 50 ring carbon atoms; an amino group; a substituent selected from an alkyl group having 1 to 50 carbon atoms and an aryl group having 6 to 50 ring carbon atoms Mono- or di-substituted amino group having a group; alkoxy group having an alkyl group having 1 to 50 carbon atoms; aryloxy group having an aryl group having 6 to 50 ring carbon atoms; alkyl group and ring having 1 to 50 carbon atoms A mono-substituted, di-substituted or tri-substituted silyl group having a substituent selected from an aryl group having 6 to 50 carbon atoms; a haloalkyl group having 1 to 50 carbon atoms; a haloalkoxy group having 1 to 50 carbon atoms; a ring A compound according to any one of claims 1 to 22 and in group selected from the group consisting of nitro group; an aromatic or non-aromatic heterocyclic group formed 5 to 50 atoms; a halogen atom; a cyano group.
An organic electroluminescent element material comprising the compound according to any one of claims 1 to 23.
An organic electroluminescence device having a cathode, an anode, and an organic thin film layer between the cathode and the anode, the organic thin film layer including one or more layers, the organic thin film layer including a light emitting layer, An organic electroluminescence device comprising at least one organic thin film layer comprising the compound according to any one of claims 1 to 23.
26. The organic electroluminescence device according to claim 25, wherein the light emitting layer includes a host material, and the host material is the compound.
27. The organic electroluminescence device according to claim 25 or 26, wherein the light emitting layer contains a dopant material, and the dopant material is a phosphorescent material.
An electronic device comprising the organic electroluminescence element according to any one of claims 25 to 27.