Organic electroluminescent compound and organic electroluminescent device comprising the same

Patent metadata

Field	Value
Publication number	US-12084446-B2
Application number	US-202017442469-A
Country	US
Kind code	B2
Filing date	Mar 24, 2020
Priority date	Mar 25, 2019
Publication date	Sep 10, 2024
Grant date	Sep 10, 2024

Abstract

The present disclosure relates to an organic electroluminescent compound, and an organic electroluminescent device comprising the same. It is possible to provide an organic electroluminescent device which can be deposited at a low deposition temperature and/or in which clogging is reduced.

First claim

The invention claimed is:

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

wherein
X 1 to X 12 each independently represent N or CR 1 ;
T 1 to T 4 each independently represent N or CR 2 ;
Y 1 to Y 3 each independently represent N or CR 3 , in which at least one of Y 1 to Y 3 is N;
L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; and
Ar 1 , Ar 2 , and R 1 to R 3 each independently represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C1-C30)alkoxy, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl, a substituted or unsubstituted (C1-C30)alkyldi(C6-C30)arylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, or a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino; or may be linked to an adjacent substituent to form a ring(s), where if a plurality of R 1 to R 3 is present, each of R 1 , each of R 2 , and each of R 3 may be the same or different.

2. The organic electroluminescent compound according to claim 1 , wherein substituents of the substituted (C1-C30)alkyl, the substituted (C6-C30)aryl(ene), the substituted (3- to 30-membered)heteroaryl(ene), the substituted (C3-C30)cycloalkyl, the substituted (C1-C30)alkoxy, the substituted tri(C1-C30)alkylsilyl, the substituted di(C1-C30)alkyl(C6-C30)arylsilyl, the substituted (C1-C30)alkyldi(C6-C30)arylsilyl, the substituted tri(C6-C30)arylsilyl, the substituted mono- or di-(C1-C30)alkylamino, the substituted mono- or di-(C6-C30)arylamino, and the substituted (C1-C30)alkyl(C6-C30)arylamino in L 1 , Ar 1 , Ar 2 , and R 1 to R 3 each independently are at least one selected from the group consisting of deuterium; a halogen; a cyano; a carboxyl; a nitro; a hydroxyl; a (C1-C30)alkyl; a halo(C1-C30)alkyl; a (C2-C30)alkenyl; a (C2-C30)alkynyl; a (C1-C30)alkoxy; a (C1-C30)alkylthio; a (C3-C30)cycloalkyl; a (C3-C30)cycloalkenyl; a (3- to 7-membered)heterocycloalkyl; a (C6-C30)aryloxy; a (C6-C30)arylthio; a (5- to 30-membered)heteroaryl unsubstituted or substituted with a (C6-C30)aryl(s); a (C6-C30)aryl unsubstituted or substituted with a (5- to 30-membered)heteroaryl(s); a tri(C1-C30)alkylsilyl; a tri(C6-C30)arylsilyl; a di(C1-C30)alkyl(C6-C30)arylsilyl; a (C1-C30)alkyldi(C6-C30)arylsilyl; an amino; a mono- or di-(C1-C30)alkylamino; a mono- or di-(C6-C30)arylamino unsubstituted or substituted with a (C1-C30)alkyl(s); a (C1-C30)alkyl(C6-C30)arylamino; a (C1-C30)alkylcarbonyl; a (C1-C30)alkoxycarbonyl; a (C6-C30)arylcarbonyl; a di(C6-C30)arylboronyl; a di(C1-C30)alkylboronyl; a (C1-C30)alkyl(C6-C30)arylboronyl; a (C6-C30)aryl(C1-C30)alkyl; and a (C1-C30)alkyl(C6-C30)aryl.

3. The organic electroluminescent compound according to claim 1 , wherein formula 1 is represented by the following formula 2 or formula 3:

wherein
a and b each independently represent an integer of 1 to 6, in which, if a and b are an integer of 2 or more, each of R 2 may be the same or different;
Y′ represents CR 4 R 5 , O, or S;
R 4 and R 5 each independently represent a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl; and
X 1 to X 12 , Y 1 to Y 3 , L 1 , Ar 1 , and Ar 2 are as defined in claim 1 .

4. The organic electroluminescent compound according to claim 1 , wherein
X 1 to X 12 each independently represent N or CR 1 ;
T 1 to T 4 each independently represent N or CR 2 ;
Y 1 to Y 3 each independently represent N or CR 3 , in which at least one of Y 1 to Y 3 is N;
L 1 represents a single bond, a substituted or unsubstituted (C6-C12)arylene, or a substituted or unsubstituted (5- to 15-membered)heteroarylene;
Ar 1 and Ar 2 each independently represent a substituted or unsubstituted (C6-C18)aryl, or a substituted or unsubstituted (5- to 15-membered)heteroaryl; and
R 1 to R 3 each independently represent hydrogen, a substituted or unsubstituted (C6-C12)aryl, or a substituted or unsubstituted (5- to 15-membered)heteroaryl; or may be linked to an adjacent substituent to form a ring(s).

5. The organic electroluminescent compound according to claim 1 , wherein
X 1 to X 12 each independently represent CR 1 ;
T 1 to T 4 each independently represent N or CR 2 ;
Y 1 to Y 3 each independently represent N or CR 3 , in which at least one of Y 1 to Y 3 is N;
L 1 represents a single bond, an unsubstituted (C6-C12)arylene, or an unsubstituted (5- to 15-membered)heteroarylene;
Ar 1 and Ar 2 each independently represent a (C6-C18)aryl unsubstituted or substituted with one or more deuterium, or an unsubstituted (5- to 15-membered)heteroaryl; and
R 1 to R 3 each independently represent hydrogen, an unsubstituted (C6-C12)aryl, or an unsubstituted (5- to 15-membered)heteroaryl; or may be linked to an adjacent substituent to form a ring(s).

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

Assignees

• Rohm & Haas Elect Materials Korea Ltd
• Rohm And Haas Electronic Mat Korea

Inventors

• Oh Hong-Se
• Jang Sung-Woo
• Kil Joon-Hyung
• Hwang Seon-Jin
• Kim Seung-Ae
• Kang Hee-Ryong
• Cho Sang-Hee
• Park Hyo-Soon

Classifications

• H10K2101/40

  Interrelation of parameters between multiple constituent active layers or sublayers, e.g. HOMO values in adjacent layers · CPC title

• H10K2101/30

  Highest occupied molecular orbital [HOMO], lowest unoccupied molecular orbital [LUMO] or Fermi energy values · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/6576

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

• H10K85/6574

  comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes · CPC title