JPWO2023189861A5 - - Google Patents

Claims (15)

A composition comprising an arylamine compound represented by any one of the following formulas (3-1) to (3-4) and an electron accepting compound represented by the following formula (81):

(In formulas (3-1) to (3-4),
Ar ² and Ar ³ each independently represent any one of formulas (4-1) to (4-3);
Each of the multiple ^R2 's is independently a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent;
Each of the multiple a2's independently represents 0 or 1;
Each of the multiple ^A2s is independently a hydrogen atom or a bridging group.

(In formulas (4-1) to (4-3),
* indicates the bond position.
Each of the multiple R ¹ 's is independently a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent;
Each of the multiple a1's is independently 0 or 1;
Each of the multiple A ^1's independently represents a hydrogen atom or a bridging group.
However, at least one of all the groups ^A1 is the bridging group.

(In formula (81), five R ⁸¹ , five R ⁸² , five R ⁸³ and five R ⁸⁴ are each independent, and R ⁸¹ to R ⁸⁴ are each independently a hydrogen atom, a deuterium atom, a halogen atom, an aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent, an aromatic heterocyclic group having 3 to 50 carbon atoms which may have a substituent, a fluorine-substituted alkyl group having 1 to 12 carbon atoms, or a bridging group.
Ph ¹ , Ph ² , Ph ³ and Ph ⁴ are symbols indicating the respective benzene rings.
X ⁺ represents a counter cation.
However, formula (81) has at least two bridging groups. The composition according to claim 1, further comprising a polymer having an arylamine structure represented by the following formula (50) as a repeating unit and having a crosslinking group:

(In formula (50),
Ar ⁵¹ represents an aromatic hydrocarbon group, an aromatic heterocyclic group, or a group in which a plurality of groups selected from aromatic hydrocarbon groups and aromatic heterocyclic groups are linked together;
Ar ⁵² represents a divalent aromatic hydrocarbon group, a divalent aromatic heterocyclic group, or a divalent group in which at least one group selected from the group consisting of the divalent aromatic hydrocarbon group and the divalent aromatic heterocyclic group is linked directly or via a linking group.
Ar ⁵¹ and Ar ⁵² may form a ring via a single bond or a linking group.
Ar ⁵¹ and Ar ⁵² may have a substituent. The composition according to claim 2, wherein the arylamine compound represented by any one of formulas (3-1) to (3-4), the electron accepting compound represented by formula (81), and the polymer having the arylamine structure represented by formula (50) as a repeating unit each independently have a crosslinking group selected from formulas (X1) to (X17) in the following crosslinking group group T:
<Crosslinking Group T>

In formulas (X1) to (X17), Q represents a direct bond or a linking group.
* indicates the bond position.
In formulae (X3), (X4), (X5) and (X9), R ¹¹⁰ represents a hydrogen atom or an alkyl group which may have a substituent.
In the formulae (X1) to (X3), the benzene ring and the naphthalene ring may have a substituent.
In addition, the substituents may be bonded to each other to form a ring.
In formula (X1) and formula (X2), the cyclobutene ring may have a substituent. The composition according to claim 3, wherein the crosslinking group is any one of formulas (X1) to (X3). The composition according to claim 2 , wherein the repeating unit represented by the formula (50) is a repeating unit represented by the following formula (54):

(In formula (54),
Ar ⁵¹ represents an aromatic hydrocarbon group, an aromatic heterocyclic group, or a group in which a plurality of groups selected from aromatic hydrocarbon groups and aromatic heterocyclic groups are linked together;
X is -C(R ²⁰⁷ )(R ²⁰⁸ )-, -N(R ²⁰⁹ )- or -C(R ²¹¹ )(R ²¹² )-C(R ²¹³ )(R ²¹⁴ )-;
R ²⁰¹ , R ²⁰² , R ²²¹ and R ²²² each independently represents an alkyl group which may have a substituent;
R ²⁰⁷ to R ²⁰⁹ and R ²¹¹ to R ²¹⁴ each independently represent a hydrogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent;
a and b each independently represent an integer from 0 to 4;
c is an integer from 0 to 3;
d is an integer from 0 to 4,
i and j each independently represent an integer from 0 to 3. The composition according to claim ^{5, wherein none of Ar2, Ar3, Ar51, Ar52, R1, R2, R201, R202 , R221 , R222 , R207 to R209 , and R211 to R214} have a substituent. The composition according to any one of claims 1 to 6, further comprising a solvent. A method for manufacturing an organic electroluminescence device having an anode and a cathode on a substrate and an organic layer between the anode and the cathode, the method including forming the organic layer by a wet film formation method using the composition according to claim 7. The method for producing an organic electroluminescent device according to claim 8, wherein the organic layer is an organic layer between the anode and the light-emitting layer. The organic electroluminescence device has an anode and a cathode on a substrate, and an organic layer between the anode and the cathode, wherein the organic layer contains a crosslinked reaction product of an arylamine compound represented by any one of the following formulas (3-1) to (3-4) and an electron-accepting compound represented by the following formula (81):

(In formulas (3-1) to (3-4),
Ar ² and Ar ³ each independently represent any one of formulas (4-1) to (4-3);
Each of the multiple ^R2 's is independently a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent;
Each of the multiple a2's independently represents 0 or 1;
Each of the multiple ^A2s is independently a hydrogen atom or a bridging group.

(In formulas (4-1) to (4-3),
* indicates the bond position.
Each of the multiple R ¹ 's is independently a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent;
Each of the multiple a1's is independently 0 or 1;
Each of the multiple A ^1's independently represents a hydrogen atom or a bridging group.
However, at least one of all the groups ^A1 is the bridging group.

(In formula (81), five R ⁸¹ , five R ⁸² , five R ⁸³ and five R ⁸⁴ are each independent, and R ⁸¹ to R ⁸⁴ are each independently a hydrogen atom, a deuterium atom, a halogen atom, an aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent, an aromatic heterocyclic group having 3 to 50 carbon atoms which may have a substituent, a fluorine-substituted alkyl group having 1 to 12 carbon atoms, or a bridging group.
Ph ¹ , Ph ² , Ph ³ and Ph ⁴ are symbols indicating the respective benzene rings.
X ⁺ represents a counter cation.
However, formula (81) has at least two bridging groups. The organic electroluminescence device has an anode and a cathode on a substrate, and an organic layer between the anode and the cathode, wherein the organic layer contains a crosslinking reaction product between an arylamine compound represented by any one of formulas (3-1) to (3-4) below and a polymer having an arylamine structure represented by formula (50) below as a repeating unit and having a crosslinking group.

(In formulas (3-1) to (3-4),
Ar ² and Ar ³ each independently represent any one of formulas (4-1) to (4-3);
Each of the multiple ^R2 's is independently a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent;
Each of the multiple a2's independently represents 0 or 1;
Each of the multiple ^A2s is independently a hydrogen atom or a bridging group.

(In formulas (4-1) to (4-3),
* indicates the bond position.
Each of the multiple R ¹ 's is independently a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent;
Each of the multiple a1's is independently 0 or 1;
Each of the multiple A ^1's independently represents a hydrogen atom or a bridging group.
However, at least one of all the groups ^A1 is the bridging group.

(In formula (50),
Ar ⁵¹ represents an aromatic hydrocarbon group, an aromatic heterocyclic group, or a group in which a plurality of groups selected from aromatic hydrocarbon groups and aromatic heterocyclic groups are linked together;
Ar ⁵² represents a divalent aromatic hydrocarbon group, a divalent aromatic heterocyclic group, or a divalent group in which at least one group selected from the group consisting of the divalent aromatic hydrocarbon group and the divalent aromatic heterocyclic group is linked directly or via a linking group.
Ar ⁵¹ and Ar ⁵² may form a ring via a single bond or a linking group.
Ar ⁵¹ and Ar ⁵² may have a substituent. The organic electroluminescent device according to claim 11, wherein none of ^Ar2 , ^Ar3 , ^Ar51 , ^Ar52 , ^R1 and ^R2 has a substituent. An organic electroluminescent device manufactured by the method for manufacturing an organic electroluminescent device according to claim 8 . A display device comprising the organic electroluminescent device according to any one of claims 10 to 12 . A lighting device comprising the organic electroluminescent device according to any one of claims 10 to 12 .