Organic electroluminescent compound, organic electroluminescent material comprising the same, and organic electroluminescent device

Patent metadata

Field	Value
Publication number	US-2021193931-A1
Application number	US-201816757844-A
Country	US
Kind code	A1
Filing date	Nov 9, 2018
Priority date	Nov 10, 2017
Publication date	Jun 24, 2021
Grant date	—

Abstract

The present disclosure relates to an organic electroluminescent compound, an organic electroluminescent material, and an organic electroluminescent device comprising the same. The organic electroluminescent compound of the present disclosure can provide an organic electroluminescent device having improved lifespan properties compared to the organic electroluminescent device comprising a conventional organic electroluminescent compound.

First claim

1 . An organic electroluminescent compound represented by the following formula 1:

wherein,
X 1 to X 3 each independently represent CR 12 or N;
at least one of X 1 to X 3 represents N;
Ar 1 to Ar 3 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;
R 1 to R 3 , and R 12 each independently represent hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; or R 1 and R 3 may be linked to an adjacent substituent to form a substituted or unsubstituted (C3-C30) mono- or polycyclic, alicyclic or aromatic ring or the combination thereof;
a and b each independently represent an integer from 0 to 4, c represents an integer from 0 to 2, when a or b is an integer of 2 or more or c is 2, each of R 1 , each of R 2 , or each of R 3 may be the same or different;
L 1 is represented by any one of the following formulae R-1 to R-3:

wherein,
R 4 represents hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3- to 30-membered)heteroaryl;
d represents an integer from 0 to 6, when d is an integer of 2 or more, each of R 4 may be the same or different;
* represents a linkage position with an adjacent ring in formula 1.

2 . The organic electroluminescent compound according to claim 1 , wherein formula 1 is represented by any one of the following formulae 1-1 to 1-5:

wherein,
X 1 to X 3 , Ar 1 to Ar 3 , R 1 to R 4 , and a to d are as defined in claim 1 .

3 . The organic electroluminescent compound according to claim 1 , wherein the substituents of the substituted (C1-C30)alkyl, the substituted (C3-C30)cycloalkyl, the substituted (C3-C30)cycloalkenyl, the substituted (3- to 7-membered)heterocycloalkyl, the substituted (C6-C30)aryl, the substituted (3- to 30-membered)heteroaryl, and the substituted (C3-C30) mono- or polycyclic, alicyclic, aromatic ring, or the combination thereof in Ar 1 to Ar 3 , R 1 to R 4 , and R 12 , each independently, are at least one selected from the group consisting of deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, (C1-C30)alkyl, halo(C1-C30)alkyl, (C2-C30)alkenyl, (C2-C30)alkynyl, (C1-C30)alkoxy, (C1-C30)alkylthio, (C3-C30)cycloalkyl; (C3-C30)cycloalkenyl, (3- to 7-membered)heterocycloalkyl, (C6-C30)aryloxy, (C6-C30)arylthio, (C6-C30)aryl-substituted or unsubstituted (5- to 30-membered)heteroaryl, (5- to 30-membered)heteroaryl-substituted or unsubstituted (C6-C30)aryl, tri(C1-C30)alkylsilyl, tri(C6-C30)arylsilyl, di(C1-C30)alkyl(C6-C30)arylsilyl, (C1-C30)alkyldi(C6-C30)arylsilyl, amino, mono- or di-(C1-C30)alkylamino, (C1-C30)alkyl-substituted or unsubstituted mono- or di-(C6-C30)arylamino, (C1-C30)alkyl(C6-C30)arylamino, (C1-C30)alkylcarbonyl, (C1-C30)alkoxycarbonyl, (C6-C30)arylcarbonyl, di(C6-C30)arylboronyl, di(C1-C30)alkylboronyl, (C1-C30)alkyl(C6-C30)arylboronyl, (C6-C30)ar(C1-C30)alkyl, and (C1-C30)alkyl(C6-C30)aryl.

4 . The organic electroluminescent compound according to claim 1 , wherein formula 1 is represented by any one of the following formulae 2 to 7:

wherein,
L 1 , X 1 to X 3 , Ar 1 to Ar 3 , R 1 to R 3 , and a to c are as defined in claim 1 .

5 . The organic electroluminescent compound according to claim 1 , wherein at least two of X 1 to X 3 represent N;
Ar 1 to Ar 3 each independently represent a substituted or unsubstituted (C6-C25)aryl; R 1 to R 4 , and R 12 each independently represent hydrogen or deuterium.

6 . The organic electroluminescent compound according to claim 1 , wherein the compound represented by formula 1 is selected from the following compounds:

Assignees

• Rohm & Haas Elect Materials Korea Ltd

Inventors

• Lee Hyo-Jung
• Rathwell Dominea
• Cho Sang-Hee
• Kang Hyun-Ju

Classifications

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C07D487/04 Primary

  Ortho-condensed systems · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K2211/1011

  Condensed systems · CPC title

• C09K2211/1059

  containing three nitrogen atoms as heteroatoms · CPC title