IP Library Granted Patent US 10,727,416
Granted Patent B2
US 10,727,416 · App. 16/088,919 · Granted Jul 28, 2020

Organic electroluminescent compound and organic electroluminescent device comprising the same

Inventor: Doo-Hyeon Moon (Hwaseong, KR)
Assignee: Rohm and Haas Electronic Materials Korea Ltd.
H01L51/0067C07D413/10C07D417/10C09K11/06H01L51/0071C09K2211/1018H01L51/0061H01L51/0069H01L51/0072H01L51/5016H01L51/5036H01L51/5056H01L51/5072H01L51/5092
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Quick Facts
Patent No.
US 10,727,416
App. No.
16/088,919
Granted
Jul 28, 2020
Kind
B2
Abstract

The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. The organic electroluminescent compound of the present disclosure provides an organic electroluminescent device having high efficiency and/or long lifespan.

Claims (29)

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

wherein

X 1 represents O or S, and X 2 represents N;

Z 1 and Z 2 each independently represent hydrogen, deuterium, or -L 1 -Het, with the proviso, at least one of Z 1 and Z 2 represents -L 1 -Het;

R represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted 3- to 30-membered heteroaryl containing at least one heteroatom selected from N, O and S;

R 1 to R 4 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C10)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted 3- to 30-membered heteroaryl containing at least one heteroatom selected from N, O and S;

L 1 represents a direct bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted 3- to 30-membered heteroarylene containing at least one heteroatom selected from N, O and S; and

Het represents a substituted or unsubstituted 3- to 30-membered heteroaryl containing at least one heteroatom selected from N, O and S.

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

wherein X 1 , X 2 , Z 1 , Z 2 , R, and R 1 to R 4 are as defined in claim 1 .

3. The organic electroluminescent compound according to claim 2 , wherein formula 3 is represented by any one of the following formulae 6 to 7:

wherein X 1 , X 2 , Z 1 , Z 2 , and R are as defined in claim 1 .

4. The organic electroluminescent compound according to claim 1 , wherein substituents of the substituted alkyl, the substituted aryl(ene), and the substituted heteroaryl(ene) in R, R 1 to R 4 , L 1 , and Het 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 3- to 30-membered heteroaryl unsubstituted or substituted with a (C6-C30)aryl, a (C6-C30) aryl unsubstituted or substituted with a 3- to 30-membered heteroaryl, a tri(C1C30) 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, 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.

5. The organic electroluminescent compound according to claim 1 , wherein X 1 represents O or S, and X 2 represents N;

Z 1 and Z 2 each independently represent hydrogen or -L 1 -Het, with the proviso, at least one of Z 1 and Z 2 represents -L 1 -Het;

R represents a substituted or unsubstituted (C6-C18)aryl, or a substituted or unsubstituted 5- to 18-membered heteroaryl;

R 1 to R 4 each independently represent hydrogen;

L 1 represents a direct bond, a substituted or unsubstituted (C6-C18)arylene, or a substituted or unsubstituted 5- to 18-membered heteroarylene; and

Het represents a substituted or unsubstituted 5- to 18-membered heteroaryl.

6. The organic electroluminescent compound according to claim 1 , wherein X 1 represents O or S, and X 2 represents N;

Z 1 and Z 2 each independently represent hydrogen or -L 1 -Het, with the proviso, at least one of Z 1 and Z 2 represents -L 1 -Het;

R represents an unsubstituted (C6-C18)aryl, or an unsubstituted 5- to 18-membered heteroaryl;

R 1 to R 4 each independently represent hydrogen;

L 1 represents a direct bond, a (C6-C18)arylene unsubstituted or substituted with a (C1-C6)alkyl, or an unsubstituted 5- to 18-membered heteroarylene; and

Het represents a 5- to 18-membered heteroaryl unsubstituted or substituted with a (C6-C12)aryl.

7. The organic electroluminescent compound according to claim 1 , wherein Het represents a substituted or unsubstituted pyridine, a substituted or unsubstituted pyrimidine, a substituted or unsubstituted triazine, a substituted or unsubstituted quinoline, a substituted or unsubstituted isoquinoline, a substituted or unsubstituted quinazoline, a substituted or unsubstituted quinoxaline, a substituted or unsubstituted triazole, a substituted or unsubstituted pyrazole, a substituted or unsubstituted benzofuran, a substituted or unsubstituted dibenzofuran, a substituted or unsubstituted benzothiophene, or a substituted or unsubstituted dibenzothiophene.

8. The organic electroluminescent compound according to claim 1 , wherein the compound represented by formula 1 is selected from the group consisting of:

9. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1 .

10. The organic electroluminescent device according to claim 9 , wherein the organic electroluminescent compound according to claim 1 is comprised in at least one of an electron transport material, an electron buffer material, and a phosphorescent host material.

Assignments (2)
CHANGE OF NAME Recorded Oct 17, 2024
From: ROHM & HAAS ELECTRONIC MATERIALS KOREA LTD
To: DUPONT SPECIALTY MATERIALS KOREA LTD
Reel/Frame 069185/0438 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 5, 2020
From: MOON, DOO-HYEON
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
Reel/Frame 054285/0196 →