IP Library Granted Patent US 11,322,692
Granted Patent B2
US 11,322,692 · App. 16/606,796 · Granted May 3, 2022

Organic electroluminescent compound and organic electroluminescent device comprising the same

Inventor: Doo-Hyeon Moon (Gyeonggi-do, KR)
H01L51/0067C07D403/04C09K11/06H01L51/0072C09K2211/1018H01L51/5072H01L51/5092H01L51/5096
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Quick Facts
Patent No.
US 11,322,692
App. No.
16/606,796
Granted
May 3, 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, high luminous efficiency, and/or improved lifespan characteristics can be provided.

Claims (18)

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

wherein

X 1 and X 3 represent CR, and X 2 and X 4 represent N;

is represented by the following formulas:

R and R 11 , each independently, represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl containing at least one heteroatom selected from B, N, O, S, Si, and P;

R 1 and R 2 , 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 containing at least one heteroatom selected from B, N, O, S, Si, and P, a substituted or unsubstituted (3- to 7-membered)heterocycloalkyl containing at least one heteroatom selected from B, N, O, S, Si, and P, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to each other to form a substituted or unsubstituted, mono- or polycyclic, (3- to 30-membered) alicyclic or aromatic ring, or a combination thereof, whose carbon atom(s) may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur;

L represents a single bond, or a substituted or unsubstituted (C6-C30)arylene, and, if n is 0, L is not a single bond;

m represents an integer of 0 to 4, n represents an integer of 0 to 2, and m+n is 1 or greater; in which if m and n are 2 or greater, each L and each

may be the same or different, and, wherein, * represents a bonding site with (L) m .

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

wherein * represents a bonding site.

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

wherein Y 1 to Y 5 , R, R 1 , R 2 , L, m, and n are as defined in claim 1 .

4. The organic electroluminescent compound according to claim 1 , wherein the substituents of the substituted alkyl, the substituted aryl(ene), the substituted heteroaryl(ene), the substituted heterocycloalkyl, the substituted cycloalkyl, and the substituted mono- or polycyclic, alicyclic or aromatic ring, or a combination thereof in R, R 1 , R 2 , R 11 , and L, 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.

5. The organic electroluminescent compound according to claim 1 , wherein R and R 11 , each independently, represent hydrogen, a substituted or unsubstituted (C6-C25)aryl, or a substituted or unsubstituted (5- to 15-membered)heteroaryl; R 1 and R 2 , each independently, represent hydrogen; and L represents a single bond, a substituted or unsubstituted (C6-C25)aryl(ene), or a substituted or unsubstituted (5- to 20-membered)heteroaryl(ene).

6. The organic electroluminescent compound according to claim 1 , wherein R and R 11 , each independently, represent hydrogen, a (C6-C25)aryl unsubstituted or substituted with a (C1-C6)alkyl(s) or a (5- to 15-membered)heteroaryl(s), or a (5- to 15-membered)heteroaryl unsubstituted or substituted with a (C6-C12)aryl(s); R 1 and R 2 , each independently, represent hydrogen; and L represents a single bond, a (C6-C25)aryl(ene) unsubstituted or substituted with a (C1-C6)alkyl(s), or a (5- to 20-membered)heteroaryl(ene) unsubstituted or substituted with a (C6-C12)aryl(s).

7. 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:

8. An organic electroluminescent 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 17, 2022
From: MOON, DOO-HYEON
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
Reel/Frame 059298/0271 →