Heterocyclic compound, and organic light-emitting element comprising same

Patent metadata

Field	Value
Publication number	US-2024254099-A1
Application number	US-202218289138-A
Country	US
Kind code	A1
Filing date	Apr 8, 2022
Priority date	May 17, 2021
Publication date	Aug 1, 2024
Grant date	—

Abstract

The present disclosure relates to a heterocyclic compound represented by Chemical Formula 1 and an organic light emitting device comprising the same.

First claim

1 . A heterocyclic compound represented by the following Chemical Formula 1:

wherein, in Chemical Formula 1,
R1 to R10 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; —P(═O)R101R102; —SiR101R102R103; a group represented by the following Chemical Formula 2; and a group represented by the following Chemical Formula 3, or two or more groups adjacent to each other bond to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heteroring, wherein R101, R102 and R103 are the same as or different from each other and each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group;
at least one of R1 to R4 is a group represented by the following Chemical Formula 2; or a group represented by the following Chemical Formula 3; and
at least one of R5 to R10 is a group represented by the following Chemical Formula 2; or a group represented by the following Chemical Formula 3,

in Chemical Formula 2 and Chemical Formula 3,
Ar1 to Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group;
L1 and L2 are the same as or different from each other, and each independently a direct bond; a substituted or unsubstituted C6 to C60 arylene group; or a substituted or unsubstituted C2 to C60 heteroarylene group; and
m and n are each an integer of 0 to 5, and when m is 2 or greater, L1s are the same as or different from each other, and when n is 2 or greater, L2s are the same as or different from each other.

2 . The heterocyclic compound of claim 1 , wherein Chemical Formula 1 is represented by the following Chemical Formula 4 or Chemical Formula 5:

in Chemical Formulas 4 and 5,
R11 to R13 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; —P(═O)R101R102; and —SiR101R102R103, or two or more groups adjacent to each other bond to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heteroring, wherein R101, R102 and R103 are the same as or different from each other and each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group;
a is an integer of 0 to 3, and when a is 2 or greater, Riis are the same as or different from each other;
b is an integer of 0 to 2, and when b is 2 or greater, R12s are the same as or different from each other,
c is an integer of 0 to 4, and when c is 2 or greater, R13s are the same as or different from each other;
Ar1, Ar2, L1 and m have the same definitions as in Chemical Formula 2; and
Ar3, L2 and n have the same definitions as in Chemical Formula 3.

3 . The heterocyclic compound of claim 1 , wherein Chemical Formula 1 is represented by the following Chemical Formula 6 or Chemical Formula 7:

in Chemical Formulas 6 and 7,
R21 to R26 are the same as or different from each other, and each independently selected from the group consisting of hydrogen; deuterium; halogen; a cyano group; a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C2 to C60 alkenyl group; a substituted or unsubstituted C2 to C60 alkynyl group; a substituted or unsubstituted C1 to C60 alkoxy group; a substituted or unsubstituted C3 to C60 cycloalkyl group; a substituted or unsubstituted C2 to C60 heterocycloalkyl group; a substituted or unsubstituted C6 to C60 aryl group; a substituted or unsubstituted C2 to C60 heteroaryl group; —P(═O)R101R102; and —SiR101R102R103, or two or more groups adjacent to each other bond to each other to form a substituted or unsubstituted C6 to C60 aromatic hydrocarbon ring; or a substituted or unsubstituted C2 to C60 heteroring, wherein R101, R102 and R103 are the same as or different from each other and each independently a substituted or unsubstituted C1 to C60 alkyl group; a substituted or unsubstituted C6 to C60 aryl group; or a substituted or unsubstituted C2 to C60 heteroaryl group;
d is an integer of 0 to 3, and when d is 2 or greater, R21s are the same as or different from each other;
Ar1, Ar2, L1 and m have the same definitions as in Chemical Formula 2; and
Ar3, L2 and n have the same definitions as in Chemical Formula 3.

4 . The heterocyclic compound of claim 1 , wherein Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

5 . The heterocyclic compound of claim 1 , wherein Ar3 is a substituted or unsubstituted C6 to C30 aryl group; or a substituted or unsubstituted C2 to C30 heteroaryl group.

6 . The heterocyclic compound of claim 1 , wherein the heterocyclic compound represented by Chemical Formula 1 does not include deuterium as a substituent, or a content of deuterium is from 1% to 100% with respect to a total number of hydrogen atoms and deuterium atoms.

7 . The heterocyclic compound of claim 1 , wherein Chemical Formula 1 is represented by any one of the following compounds:

Assignees

• Lt Materials Co Ltd

Inventors

• Kim Ji Un
• Dong Gwang Il
• Lee Yong Hui
• Jeong Won Jang
• Kim Dong Jun

Classifications

• H10K50/18

  Carrier blocking layers · CPC title

• H10K85/636

  comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom · CPC title

• H10K50/15

  Hole transporting layers · CPC title

• H10K85/6576 Primary

  comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene · CPC title

• H10K99/00

  Subject matter not provided for in other groups of this subclass · CPC title