IP Library Granted Patent US 9,997,724
Granted Patent B2
US 9,997,724 · App. 15/509,588 · Granted Jun 12, 2018

Organic electroluminescent compound and organic electroluminescent device comprising the same

Inventors: Bitnari Kim (Cheonan, KR); Hee-Ryong Kang (Seoul, KR); Hyun-Ju Kang (Gwangmyeong, KR); Jin-Ri Hong (Cheonan, KR); Young-Mook Lim (Cheonan, KR); Doo-Hyeon Moon (Hwaseong, KR)
Assignee: Rohm and Haas Electronic Materials Korea Ltd.
H01L51/0072C07D471/22C07D487/16C07D487/22C07D519/00C09K11/06H01L51/0061H01L51/0073H01L51/0074C09K2211/1007C09K2211/1014C09K2211/1018C09K2211/1022H01L51/001H01L51/5016H01L51/5056H01L51/5088H01L2251/558
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Quick Facts
Patent No.
US 9,997,724
App. No.
15/509,588
Granted
Jun 12, 2018
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 has good color purity, solubility, and thermal stability. By comprising the organic electroluminescent compound of the present disclosure, an organic electroluminescent device showing low driving voltage, excellent current and power efficiencies, and significantly improved lifespan can be provided.

Claims (30)

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

wherein

ring A and ring B, each independently, represent any one of the following formulae 2-1 to 2-3:

X and Y, each independently, represent —CR 8 — or —N—; provided that both X and Y are not —CR 8 —, simultaneously;

R 1 to R 8 , each independently, represent hydrogen, 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 may be linked to an adjacent substituent(s) to form a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring; and

the heteroaryl of the substituted or unsubstituted 3- to 30-membered heteroaryl contains at least one hetero atom selected from N, O and S.

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 triarylsilyl, the substituted mono- or di-alkylamino, the substituted mono- or di-arylamino and the substituted alkylarylamino in R 1 to R 8 , each independently, are 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 5- to 30-membered heteroaryl unsubstituted or substituted with a (C6-C30)aryl, a (C6-C30)aryl unsubstituted or substituted with a 5- 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.

3. The organic electroluminescent compound according to claim 1 , wherein X and Y, each independently, represent —CR 8 — or —N—; provided that both X and Y are not —CR 8 —, simultaneously;

ring A and ring B, each independently, represent any one of the following formulae 2-1 to 2-3:

R 1 to R 8 , each independently, represent hydrogen, a substituted or unsubstituted (C6-C20)aryl, a substituted or unsubstituted 5- to 25-membered heteroaryl, or a substituted or unsubstituted di(C6-C20)arylamino; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring.

4. The organic electroluminescent compound according to claim 1 , wherein X and Y, each independently, represent —CR 8 — or —N—; provided that both X and Y are not —CR 8 —, simultaneously;

ring A and ring B, each independently, represent any one of the following formulae 2-1 to 2-3:

R 1 to R 7 , each independently, represent hydrogen; a (C6-C20)aryl unsubstituted or substituted with a (C1-C6)alkyl, a 5- to 20-membered heteroaryl or a di(C6-C12)arylamino; or a 5- to 20-membered heteroaryl unsubstituted or substituted with a (C1-C6)alkyl, a (C6-C12)aryl or a di(C6-C12)arylamino; or may be linked to an adjacent substituent(s) to form a substituted or unsubstituted benzene ring or a substituted or unsubstituted naphthalene ring; provided that R 1 to R 7 are not hydrogen, simultaneously; and

R 8 represents hydrogen or a (C1-C6)alkyl.

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

R 1 to R 7 , each independently, represent hydrogen, a (C1-C20)alkyl, or any one of the following formulae 3-1 to 3-6; or may be linked to an adjacent substituent(s) to form a benzene ring unsubstituted or substituted with a (C1-C6)alkyl, or a naphthalene ring unsubstituted or substituted with a (C1-C6)alkyl; provided that R 1 to R 7 are not hydrogen, simultaneously; and R 8 represents hydrogen or a (C1-C6)alkyl;

wherein,

Ar 1 and Ar 2 , each independently, represent hydrogen, a substituted or unsubstituted (C1-C30)alkyl, or a substituted or unsubstituted (C6-C30)aryl; provided that Ar 1 and Ar 2 are not fluorenyl;

L a , L b , L c , and L d , each independently, represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted 3- to 30-membered heteroarylene;

Z represents —S—, —O—, —NR 11 —, or —CR 12 R 13 —;

R 11 to R 13 , each independently, represent hydrogen, 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, or a substituted or unsubstituted 3- to 7-membered heterocycloalkyl; or 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;

R 31 to R 39 , each independently, represent hydrogen, deuterium, a halogen, a cyano, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C3-C30)cycloalkenyl, a substituted or unsubstituted 3- to 7-membered heterocycloalkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted 3- to 30-membered heteroaryl, a substituted or unsubstituted tri(C1-C30)alkylsilyl, a substituted or unsubstituted tri(C6-C30)arylsilyl, 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 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(s) to form a substituted or unsubstituted 3- to 30-membered, mono- or polycyclic, alicyclic or aromatic ring, whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen, and sulfur;

the heteroaryl(ene) and heterocycloalkyl, each independently, contain at least one hetero atom selected from nitrogen, oxygen, and sulfur;

a represents an integer of 1 to 3;

b to d and f, each independently, represent an integer of 1 to 4;

e, g, and h, each independently, represent an integer of 1 to 5; and

where a, b, c, d, e, f, g, or h is integers of 2 or more, each of R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , or R 39 may be the same or different.

6. The organic electroluminescent compound according to claim 5 , wherein at least one of R 1 to R 7 is selected from formulae 3-3 to 3-5, and Z of formula 3-3 represents —NR 11 —.

7. The organic electroluminescent compound according to claim 1 , wherein the compound represented by formula 1 is 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 May 2, 2018
From: KIM, BITNARI; KANG, HEE-RYONG; KANG, HYUN-JU; HONG, JIN RI; LIM, YOUNG-MOOK; MOON, DOO-HYEON
To: ROHM AND HAAS ELECTRONICS MATERIALS KOREA LTD.
Reel/Frame 045692/0612 →
Priority Claims (2)
KR 10-2014-0130061 · Sep 29, 2014 · national
KR 10-2015-0135881 · Sep 24, 2015 · national
Continuity (1)
Related Publication 20170301867A1 · Oct 19, 2017