IP Library Granted Patent US 11,289,662
Granted Patent B2
US 11,289,662 · App. 16/479,616 · Granted Mar 29, 2022

Organic electroluminescent compound and organic electroluminescent device comprising the same

Inventor: Jeong-Eun Yang (Gyeonggi-do, KR)
H01L51/0072C07D471/14C09K11/06H01L51/0067C09K2211/1007C09K2211/1018H01L51/5012
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Quick Facts
Patent No.
US 11,289,662
App. No.
16/479,616
Granted
Mar 29, 2022
Kind
B2
Abstract

The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. By comprising the organic electroluminescent compound of the present disclosure, an organic electroluminescent device having low driving voltage and/or high luminous efficiency can be provided. At the same time or selectively, an organic electroluminescent device having excellent lifespan characteristic and/or formable of a thin film of excellent quality can be provided.

Claims (33)

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

wherein

Ar 1 and Ar 2 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 (5- to 30-membered)heteroaryl, a substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl;

Ar 3 and Ar a each independently represent hydrogen, deuterium, a halogen, a cyano, —NR 11 R 12 , a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl; and at least one of two Ar 3 's and two Ar 4 's are linked to each other to form a fused ring of

in which * represents a bonding site of Ar 3 or Ar 4 ;

R 11 and R 12 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (5- to 30-membered)heteroaryl, a substituted or unsubstituted (3- to 7-membered) heterocycloalkyl, or a substituted or unsubstituted (C3-C30)cycloalkyl;

L 1 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene;

Ar 5 represents hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;

Ar 6 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;

the heteroaryl contains at least one heteroatom selected from B, N, O, S, Si, and P;

a and b each independently represent an integer of 1 to 5, and c to e each independently represent an integer of 1 to 4;

where a to e is an integer of 2 or more, each Ar 1 , each Ar 2 , each Ar 3 , each Ar 4 , and each Ar 5 may be the same or different.

2. The organic electroluminescent compound according to claim 1 , wherein the substituents of the substituted (C1-C30)alkyl, the substituted (C6-C30)aryl(ene), the substituted (5- to 30-membered)heteroaryl, the substituted (3- to 7-membered)heterocycloalkyl, and the substituted (C3-C30)cycloalkyl in Ar 1 to Ar 6 , and L 1 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 any one of the following formulas 2 and 3:

wherein

Ar 1 to Ar 6 , L 1 , and a to e are as defined in claim 1 .

4. The organic electroluminescent compound according to claim 1 , wherein

Ar 1 and Ar 2 each independently represent hydrogen, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl;

Ar 3 and Ar 4 each independently represent hydrogen, a halogen, —NR 11 R 12 , a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl; and at least one of two Ar 3 's and two Ar 4 's are linked to each other to form a fused ring of

L 1 represents a single bond;

R 11 and R 12 each independently represent hydrogen, a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl;

Ar 5 represents hydrogen, or a substituted or unsubstituted (C6-C20)aryl; and

Ar 6 represents a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl.

5. The organic electroluminescent compound according to claim 1 , wherein

Ar 1 and Ar 2 each independently represent hydrogen, an unsubstituted (C6-C20)aryl, or a (5- to 20-membered)heteroaryl substituted with a (C6-C12)aryl(s);

Ar 3 and Ar 4 each independently represent hydrogen, a (C6-C20)aryl unsubstituted or substituted with a nitro(s), or a (5- to 20-membered)heteroaryl unsubstituted or substituted with a (C6-C12)aryl(s); and at least one of two Ar 3 's and two Ar 4 's are linked to each other to form a fused ring of

L 1 represents a single bond;

Ar 5 represents hydrogen, or an unsubstituted (C6-C20)aryl; and

Ar 6 represents an unsubstituted (C6-C20)aryl, or a (5- to 20-membered)heteroaryl unsubstituted or substituted with a (C6-C12)aryl(s).

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

7. An organic electroluminescent material comprising the organic electroluminescent compound according to claim 1 .

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

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

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 Mar 23, 2022
From: YANG, JEONG-EUN
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
Reel/Frame 059381/0078 →