IP Library Granted Patent US 11,737,353
Granted Patent B2
US 11,737,353 · App. 17/670,572 · Granted Aug 22, 2023

Plurality of host materials and organic electroluminescent device comprising the same

Inventors: Sang-Hee Cho (Gyeonggi-do, KR); Doo-Hyeon Moon (Gyeonggi-do, KR); Bitnari Kim (Gyeonggi-do, KR)
H10K85/631C09K11/06H10K85/624H10K85/654H10K85/656H10K50/11H10K50/12H10K2101/10H10K2101/90
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Quick Facts
Patent No.
US 11,737,353
App. No.
17/670,572
Granted
Aug 22, 2023
Kind
B2
Abstract

The present disclosure relates to a plurality of host materials and an organic electroluminescent device comprising the same. The organic electroluminescent device of the present disclosure can exhibit excellent lifespan characteristics while maintaining high luminous efficiency by including a specific combination of a plurality of host compounds.

Claims (29)

1. A plurality of host materials comprising at least one of a first host compound and at least one of a second host compound, wherein the first host compound is represented by the following formula 2, and the second host compound is represented by the following formula 3:

wherein,

X 1 represents —N═, —NR 7 —, —O— or —S—,

Y 1 represents —N═, —NR 8 —, —O— or —S—, provided that when X 1 represents —N═, Y 1 represents —NR 8 —, —O— or —S—, and when X 1 represents —NR 7 —, Y 1 represents —N═, —O— or —S—,

R 1 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl,

R 2 , R 3 and R 5 to R 8 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 (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 to form a substituted or unsubstituted, (C3-C30) mono- or polycyclic, alicyclic, or aromatic ring, whose carbon atom may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur,

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 1, b represents 1 or 2, and e represents an integer of 1 to 4,

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

wherein,

X 11 represents —N═, —NR 17 —, —O— or —S—,

Y 11 represents —N═, —NR 18 —, —O— or —S—, provided that when X 11 represents —N═, Y 11 represents —NR 18 —, —O— or —S—, and when X 11 represents —NR 17 —, Y 11 represents —N═, —O— or —S—,

X represents N,

R 11 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl,

R 12 to R 18 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 (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 to form a substituted or unsubstituted, (C3-C30) mono- or polycyclic, alicyclic, or aromatic ring, whose carbon atom may be replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur,

L 2 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene,

a′ represents 1, b′ and c′ each independently represent 1 or 2, d′ represents an integer of 1 to 4,

the heteroaryl(ene) contains at least one heteroatom selected from B, N, O, S, Si, and P.

2. The host materials according to claim 1 , wherein the formula 2 is represented by any one of the following formulae 1-4 to 1-5:

wherein,

R 1 to R 3 , R 5 and R 6 , L 1 and a, b, and e are as defined in claim 1 .

3. The host materials according to claim 1 , wherein the formula 3 is represented by any one of the following formulae 3-1 to 3-6:

wherein,

R 11 to R 18 , L 2 , X and a′ to d′ are as defined in claim 1 .

4. The host materials according to claim 1 , wherein the substituents of the substituted alkyl, the substituted alkoxy, the substituted cycloalkyl, the substituted aryl(ene), the substituted heteroaryl(ene), the substituted trialkylsilyl, the substituted triarylsilyl, 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, in R 1 to R 3 , R 5 to R 8 , R 11 to R 18 , L 1 and L 2 , 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; (3- to 7-membered)heterocycloalkyl; (C6-C30)aryloxy; (C6-C30)arylthio; (C6-C30)aryl- or di(C6-C30)arylamino-substituted or unsubstituted (3- to 30-membered)heteroaryl; cyano-, (3-to 30-membered)heteroaryl- or tri(C6-C30)arylsilyl-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; a 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.

5. The host materials according to claim 1 , wherein the compound represented by formula 2 is selected from the group consisting of:

6. The host materials according to claim 1 , wherein the compound represented by formula 3 is selected from the group consisting of:

7. An organic electroluminescent device comprising: an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein the light-emitting layer comprises a host and a phosphorescent dopant, wherein the host comprises the host materials according to claim 1 .

Assignments (3)
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 Jun 29, 2023
From: CHO, SANG-HEE; MOON, DOO-HYEON; KIM, BITNARI
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
Reel/Frame 064108/0063 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 23, 2022
From: CHO, SANG-HEE; MOON, DOO-HYEON; KIM, BITNARI
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
Reel/Frame 059380/0793 →
Priority Claims (2)
KR 10-2017-0025749 · Feb 27, 2017 · national
KR 10-2018-0020359 · Feb 21, 2018 · national
Continuity (2)
Continuation 16481644
Related Publication 20220165956A1 · May 26, 2022