IP Library Granted Patent US 10,547,010
Granted Patent B2
US 10,547,010 · App. 15/777,747 · Granted Jan 28, 2020

Organic electroluminescent compounds and organic electroluminescent device comprising the same

Inventor: Doo-Hyeon Moon (Hwaseong, KR)
Assignee: Rohm and Haas Electronic Materials Korea Ltd.
H01L51/0067C07D487/16C09K11/06H01L51/0072C09K2211/1018H01L51/001H01L51/5016H01L51/5064H01L51/5072H01L51/5088H01L51/56H01L2251/558
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Quick Facts
Patent No.
US 10,547,010
App. No.
15/777,747
Granted
Jan 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 a remarkably improved lifespan.

Claims (30)

1. An organic electroluminescent compound represented by the following formula

wherein

X and Y, each independently, represent CR 4 or N;

L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene;

A represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered) heteroaryl;

R 1 , R 2 , and 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 two or more R 1 's may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (3 to 30-membered), mono- or polycyclic, alicyclic or aromatic ring, or a fused ring of the alicyclic ring and the aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from the group consisting of nitrogen, oxygen, and sulfur; or two or more R 2 's may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (3 to 30-membered), mono- or polycyclic, alicyclic or aromatic ring, or a fused ring of the alicyclic ring and the aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from the group consisting of nitrogen, oxygen, and sulfur; or two or more R 3 's may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (3 to 30-membered), mono- or polycyclic, alicyclic or aromatic ring, or a fused ring of the alicyclic ring and the aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from the group consisting of nitrogen, oxygen, and sulfur;

R 4 represents 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;

wherein the heteroaryl(ene) contains one or more heteroatoms selected from the group consisting of B, N, O, S, Si, and P;

a, b, and c, each independently, represent an integer of 1 to 3,

and when a, b, or c is an integer of 2 or more, each of R 1 , R 2 or R 3 may be the same or different.

2. The organic electroluminescent compound according to claim 1 , wherein the organic electroluminescent compound of formula 1 is represented by any of the following formulae 2, 3, 6, 7, 8, and 9:

wherein L 1 , R 1 , R 2 , R 3 , R 4 , a, b, and c are as defined in claim 1 .

3. The organic electroluminescent compound according to claim 1 , wherein the organic electroluminescent compound of formula 1 is represented by the following formula 10:

wherein

X, Y, L 1 , A, R 3 , and c are as defined in claim 1 ,

Z represents O, S, CR 5 R 6 , or NR 7 ,

R 5 , R 6 , and R 7 , each independently, are the same as R 4 defined in claim 1 , and

d and e, each independently, represent an integer of 0 or 1.

4. The organic electroluminescent compound according to claim 1 , wherein in the L 1 , A, R 1 , R 2 , R 3 , and, R 4 , the substituent of the substituted aryl(ene), the substituted heteroaryl(ene), the substituted alkyl, the substituted cycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted triarylsilyl, the substituted mono- or di-alkylamino, the substituted mono- or di-arylamino, the substituted alkylarylamino, and the substituted mono- or polycyclic, alicyclic or aromatic ring, or a fused ring of the alicyclic ring and the aromatic ring, each independently, is at least one selected from the group consisting of deuterium; a halogen; a cyano; a carboxy; a nitro; a hydroxy; 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 substituted or unsubstituted with a (C1-C30)alkyl or a (C6-C30)aryl; a (C6-C30)aryl substituted or unsubstituted with a (3 to 30-membered) heteroaryl; 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; 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 the compound represented by formula 1 is selected from the group consisting of:

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

7. An organic electroluminescent compound, wherein the organic electroluminescent compound is represented by any of the following formulae 4 and 5:

L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered) heteroarylene;

R 1 , R 2 , and 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 two or more R 1 's may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (3 to 30-membered), mono- or polycyclic, alicyclic or aromatic ring, or a fused ring of the alicyclic ring and the aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from the group consisting of nitrogen, oxygen, and sulfur; or two or more R 2 's may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (3 to 30-membered), mono- or polycyclic, alicyclic or aromatic ring, or a fused ring of the alicyclic ring and the aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from the group consisting of nitrogen, oxygen, and sulfur; or two or more R 3 's may be linked to an adjacent substituent(s) to form a substituted or unsubstituted (3 to 30-membered), mono- or polycyclic, alicyclic or aromatic ring, or a fused ring of the alicyclic ring and the aromatic ring, whose carbon atom(s) may be replaced with at least one heteroatom selected from the group consisting of nitrogen, oxygen, and sulfur;

R 4 represents 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;

wherein the heteroaryl(ene) contains one or more heteroatoms selected from the group consisting of B, N, O, S, Si, and P;

a, b, and c, each independently, represent an integer of 1 to 3,

and when a, b, or c is an integer of 2 or more, each of R 1 , R 2 or R 3 may be the same or different.

8. The organic electroluminescent compound according to claim 7 , wherein the compound represented by formula 4 or formula 5 is selected from the group consisting of:

9. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 7 .

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 Jan 24, 2020
From: MOON, DOO-HYEON
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
Reel/Frame 051612/0226 →
Priority Claims (2)
KR 10-2015-0172324 · Dec 4, 2015 · national
KR 10-2016-0158003 · Nov 25, 2016 · national
Continuity (1)
Related Publication 20180337340A1 · Nov 22, 2018
Cited By (1)
US 12,522,624