JP2021172629A5

JP2021172629A5 -

Info

Publication number: JP2021172629A5
Application number: JP2020079716A
Authority: JP
Filing date: 2020-04-28
Publication date: 2023-05-09

Claims

A compound represented by the following formula (1):
Cz-L-Ar (1)
[In the formula,
Cz is represented by the following formula (2):

(In the formula,
Z is a single bond, —C(R ^29a )(R ^29b )—, —O—, —S—, or —N(R ^29c )—;
R ²² and R ²⁷ are each an alkylcarbonyl group, an alkylsulfonyl group, a perfluoroalkyl group, a cyano group, or a nitro group ;
R ²³ and R ²⁶ are each an electron donating group,
R ²¹ , R ²⁴ , R ²⁵ , R ²⁸ , R ^29a , R ^29b , and R ^29c are each a hydrogen atom, an electron-withdrawing group, or an electron-donating group;
The wavy line indicates the binding site with L)
is a group represented by
L is a single bond or a phenylene group optionally having a substituent,
Ar is a group selected from the group consisting of an aryl group and a heteroaryl group, and the group is an optionally substituted N,N-diarylamino group, optionally substituted It may have at least one substituent selected from a cycloalkyl group, an optionally substituted aryl group, and an optionally substituted heteroaryl group (wherein Ar is , is not a group represented by the formula (2))].

Ar is a group selected from the group consisting of a phenyl group, a condensed bi- to hexacyclic aryl group, and a nitrogen-containing heteroaryl group, and the group is optionally substituted N,N-diaryl at least one substituent selected from an amino group, an optionally substituted cycloalkyl group, an optionally substituted aryl group, and an optionally substituted heteroaryl group (where Ar is not a group represented by formula (2)).

Ar is represented by the following formula (3):

(In the formula,
X ³¹ to X ³⁵ are each -N= or -C(R ³ )=,
R ³ is a hydrogen atom, an optionally substituted N,N-diarylamino group, an optionally substituted cycloalkyl group, an optionally substituted aryl group, or A heteroaryl group optionally having a substituent,
Two R ³ that may exist in an ortho positional relationship with each other may be bonded to form an aromatic ring, and the aromatic ring is an optionally substituted N,N-diarylamino group , an optionally substituted cycloalkyl group, an optionally substituted aryl group, and an optionally substituted heteroaryl group. may be
The wavy line indicates the binding site with L)
The compound according to claim 1 or 2, which is a group represented by.

The group represented by formula (3) is represented by the following formulas (3-1) to (3-4):

(In the formula,
R ³¹¹ , R ³¹² , R ³²¹ to R ³²³ , R ³³¹ to R ³³⁶ and R ³⁴¹ to R ³⁴⁶ are each a hydrogen atom, an optionally substituted N,N-diarylamino group, a substituent A cycloalkyl group optionally having a, an aryl group optionally having a substituent, or a heteroaryl group optionally having a substituent,
The wavy line indicates the binding site with L)
The compound according to claim 3, which is a group represented by any one of

L is a phenylene group optionally having at least one substituent selected from the group consisting of the group represented by the formula (2) and the group represented by the formula (3), or 5. A compound according to 4.

A compound according to any one of claims 1 to 5, wherein Z is a single bond.

A compound according to any one of claims 1 to 6, wherein R ²² and R ²⁷ are each a perfluoroalkyl group or a cyano group.

R ²³ and R ²⁶ are each an alkyl group, an alkoxy group, a trialkylsilyl group, an optionally substituted N,N-diarylamino group, an optionally substituted cycloalkyl group, The compound according to any one of claims 1 to 7, which is an optionally substituted aryl group or an optionally substituted heteroaryl group.

R ²¹ , R ²⁴ , R ²⁵ and R ²⁸ are hydrogen atoms, or R ²¹ and R ²⁸ are each electron-donating groups, and R ²⁴ and R ²⁵ are each electron-withdrawing groups is
A compound according to any one of claims 1-8.

A compound represented by the following formula (4):

[In the formula,
X ⁴¹ to X ⁴³ are each -N= or -C(R ⁴⁴ )=,
R ⁴¹ to R ⁴⁴ each represent a hydrogen atom, an optionally substituted N,N-diarylamino group, an optionally substituted cycloalkyl group, or an optionally substituted a good aryl group or an optionally substituted heteroaryl group (provided that at least one of R ⁴¹ to R ⁴³ is a group represented by formula (2))];
A compound represented by the following formula (5):

[In the formula,
X ⁵¹ to X ⁵³ are each -N= or -C(R ⁵⁸ )=,
R ⁵¹ , R ⁵² and R ⁵⁸ each represent a hydrogen atom, an optionally substituted N,N-diarylamino group, an optionally substituted cycloalkyl group, or a substituted an optionally substituted aryl group, or an optionally substituted heteroaryl group,
R ⁵³ to R ⁵⁷ are each a hydrogen atom or a group represented by formula (2) (with the proviso that at least one of R ⁵³ to R ⁵⁷ is a group represented by formula (2))] ;
A compound represented by the following formula (6):

[In the formula,
X ⁶¹ to X ⁶⁷ are each -N= or -C(R ⁶⁶ )=,
R ⁶¹ to R ⁶⁵ are each a hydrogen atom or a group represented by formula (2) (provided that at least one of R ⁶¹ to R ⁶⁵ is a group represented by formula (2));
R ⁶⁶ is a hydrogen atom, an optionally substituted N,N-diarylamino group, an optionally substituted cycloalkyl group, an optionally substituted aryl group, or is a heteroaryl group optionally having a substituent];
A compound represented by the following formula (7):

[In the formula,
X ⁷¹ to X ⁷⁶ are each -N= or -C(R ⁷⁹ )=,
R ⁷¹ to R ⁷⁴ and R ⁷⁹ are each a hydrogen atom, an optionally substituted N,N-diarylamino group, an optionally substituted cycloalkyl group, or a substituted an optionally substituted aryl group, or an optionally substituted heteroaryl group,
R ⁷⁵ to R ⁷⁸ are a hydrogen atom or a group represented by formula (2) (provided that at least one of R ⁷⁵ to R ⁷⁸ is a group represented by formula (2)); and A compound represented by the following formula (8):

[In the formula,
X ⁸¹ to X ⁸⁶ are each -N= or -C(R ⁸⁹ )=,
R ⁸¹ to R ⁸⁴ and R ⁸⁹ are each a hydrogen atom, an optionally substituted N,N-diarylamino group, an optionally substituted cycloalkyl group, or a substituted an optionally substituted aryl group, or an optionally substituted heteroaryl group,
R ⁸⁵ to R ⁸⁸ are a hydrogen atom or a group represented by formula (2) (provided that at least one of R ⁸⁵ to R ⁸⁸ is a group represented by formula (2))]
2. The compound of claim 1, selected from the group consisting of:

A delayed fluorescence material containing the compound according to any one of claims 1 to 10.

An organic light-emitting device comprising the compound according to any one of claims 1 to 10.

13. The organic light-emitting device according to claim 12, which is an organic EL device.

Formula (9) below:

(In the formula,
R ⁹¹ and R ⁹⁴ are each a perfluoroalkyl group or a cyano group,
R ⁹² and R ⁹³ are each an alkyl group, an alkoxy group, a trialkylsilyl group, an optionally substituted N,N-diarylamino group, an optionally substituted cycloalkyl group, an optionally substituted aryl group or an optionally substituted heteroaryl group,
Z ⁹ is a single bond, -C(R ⁹⁵ )(R ⁹⁶ )-, -O-, -S-, or -N(R ⁹⁷ )-;
R ⁹⁵ to R ⁹⁷ are each a hydrogen atom, an electron-withdrawing group, or an electron-donating group)
A compound represented by