IP Library Granted Patent US 10,991,889
Granted Patent B2
US 10,991,889 · App. 16/630,871 · Granted Apr 27, 2021

Organic electroluminescent compound and organic electroluminescent device comprising the same

Inventors: Hyun Kim (Gyeonggi-do, KR); Doo-Hyeon Moon (Gyeonggi-do, KR); Sang-Hee Cho (Gyeonggi-do, KR); Sung-Wook Cho (Gyeonggi-do, KR)
Assignee: Rohm and Haas Electronic Materials Korea Ltd.
H01L51/0067C07D401/10C09K11/06H01L51/0072C09K2211/1018H01L51/50H01L51/5012H01L51/5072H01L2251/558
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Quick Facts
Patent No.
US 10,991,889
App. No.
16/630,871
Granted
Apr 27, 2021
Kind
B2
Abstract

The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same. An organic electroluminescent device having a low driving voltage, a high luminous efficiency and/or excellent color coordinates can be provided by comprising the organic electroluminescent compound according to the present disclosure.

Claims (22)

1. An organic electroluminescent compound represented by the following formula 7:

wherein,

R 1 to R 3 each independently represent hydrogen, deuterium, halogen, 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, provided that at least two of R 1 to R 3 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (5- to 30-membered)heteroaryl;

B 1 and B 2 each independently represent hydrogen, deuterium, halogen, 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 (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;

Ar 1 and Ar 2 each independently represent 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; or may be linked to an adjacent substituent to form a substituted or unsubstituted (3- to 30-membered) mono- or polycyclic, alicyclic or aromatic ring, or a combination thereof; and

R 11 to R 14 each independently represent hydrogen, deuterium, halogen, 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 (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 substituted or unsubstituted (3- to 30-membered) mono- or polycyclic, alicyclic or aromatic ring, or a combination thereof.

2. The organic electroluminescent compound according to claim 1 , wherein the substituents of the substituted alkyl, the substituted aryl, the substituted heteroaryl, the substituted cycloalkyl, the substituted alkoxy, the substituted trialkylsilyl, the substituted dialkylarylsilyl, the substituted alkyldiarylsilyl, the substituted arylsilyl, the substituted mono- or di-alkylamino, the substituted mono- or di-arylamino, the substituted alkylarylamino, and the substituted mono- or polycyclic, alicyclic, aromatic ring, or the combination thereof, in R 1 to R 3 , B 1 , B 2 , Ar 1 Ar 2 , and R 11 to R 14 , are each independently at least one selected from the group consisting of deuterium; halogen; cyano; carboxyl; nitro; hydroxyl; (C1-C30)alkyl; halo(C1-C30)alkyl; (C2-C30)alkenyl; (C2-C30)alkynyl; (C1-C30)alkoxy; (C1-C30)alkylthio; (C3-C30)cycloalkyl; (C3-C30)cycloalkenyl; (3- to 7-membered)heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (C6-C30)aryl-substituted or unsubstituted (5- to 30-membered)heteroaryl; (5- to 30-membered)heteroaryl-substituted or unsubstituted (C6-C30)aryl; tri(C1-C30)alkylsilyl; tri(C6-C30)arylsilyl; di(C1-C30)alkyl(C6-C30)arylsilyl; (C1-C30)alkyldi(C6-C30)arylsilyl; amino; a mono- or di-(C1-C30)alkylamino; (C1-C30)alkyl-substituted or unsubstituted mono- or di-(C6-C30)arylamino; (C1-C30)alkyl(C6-C30)arylamino; (C1-C30)alkylcarbonyl; (C1-C30)alkoxycarbonyl; (C6-C30)arylcarbonyl; di(C6-C30)arylboronyl, di(C1-C30)alkylboronyl, (C1-C30)alkyl(C6-C30)arylboronyl; (C6-C30)ar(C1-C30)alkyl; and (C1-C30)alkyl(C6-C30)aryl.

3. The organic electroluminescent compound according to claim 1 , wherein, R 1 and R 3 each independently represent a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl;

R 2 represents hydrogen;

B 1 and B 2 represent hydrogen;

Ar 1 and Ar 2 each independently represent a substituted or unsubstituted (C1-C6)alkyl, or a substituted or unsubstituted (C6-C12)aryl, or may be linked to an adjacent substituent to form a substituted or unsubstituted (5- to 15-membered) polycyclic, alicyclic, or aromatic ring, or a combination thereof; and

R 11 to R 14 each independently represent hydrogen or a substituted or unsubstituted (C6-C12)aryl.

4. The organic electroluminescent compound according to claim 1 , wherein, R 1 and R 3 each independently represent a substituted or unsubstituted (C6-C20)aryl, or a substituted or unsubstituted (5- to 20-membered)heteroaryl, wherein the substituents of the substituted aryl are each independently (C6-C15)aryl-substituted or unsubstituted (5- to 25-membered)heteroaryl, and wherein the substituents of the substituted heteroaryl are each independently (C6-C15)aryl;

R 2 represents hydrogen;

B 1 and B 2 represent hydrogen;

Ar 1 and Ar 2 each independently represent an unsubstituted (C1-C6)alkyl, or an unsubstituted (C6-C12)aryl; or may be linked to an adjacent substituent to form an unsubstituted (5- to 15-membered) polycyclic aromatic ring; and

R 11 to R 14 each independently represent halogen or an unsubstituted (C6-C12)aryl.

5. The organic electroluminescent compound according to claim 1 , wherein the compound represented by formula 7 is selected from the group consisting of:

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

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

8. The organic electroluminescent device according to claim 7 , wherein the organic electroluminescent compound is contained in at least one layer of an electron buffer layer and an electron transport layer.

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 →
CORRECTIVE ASSIGNMENT TO CORRECT THE THE ASSIGNMENT THAT WAS RECORDED UNDER THE INCORRECTI APPLICATION NUMBER PREVIOUSLY RECORDED AT REEL: 056500 FRAME: 0463. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jun 16, 2021
From: KIM, HYUN; MOON, DOO-HYEON; CHO, SANG-HEE; CHO, SUNG-WOOK
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
Reel/Frame 056668/0771 →