IP Library Granted Patent US 11,706,984
Granted Patent B2
US 11,706,984 · App. 17/075,581 · Granted Jul 18, 2023

Plurality of host materials and organic electroluminescent device comprising the same

Inventors: So-Young Jung (Gyeonggi-do, KR); Su-Hyun Lee (Gyeonggi-do, KR); Mi-Ja Lee (Gyeonggi-do, KR); Doo-Hyeon Moon (Gyeonggi-do, KR); Sang-Hee Cho (Gyeonggi-do, KR)
H10K85/6572H10K85/615H10K85/626H10K85/654H10K85/6574H10K85/6576H10K50/11H10K85/342H10K2101/10H10K2101/90
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 11,706,984
App. No.
17/075,581
Granted
Jul 18, 2023
Kind
B2
Abstract

The present disclosure relates to a plurality of host materials comprising a first host material comprising a compound represented by formula 1, and a second host material comprising a compound represented by formula 2, and an organic electroluminescent device comprising the same. By comprising a specific combination of compounds of the present disclosure as host materials, it is possible to provide an organic electroluminescent device having higher luminous efficiency and/or longer lifetime properties as compared with a conventional organic electroluminescent device.

Claims (24)

1. A plurality of host materials comprising a first host material comprising a compound represented by the following formula 1, and a second host material comprising a compound represented by the following formula 3:

wherein,

ring A, ring B, and ring C, each independently, represent a substituted or unsubstituted benzene ring, or a substituted or unsubstituted naphthalene ring;

Y represents O, S, or NRa;

Ra represents —L 2 —Ar 2 ;

Ar 1 and Ar 2 , each independently, represent a substituted or unsubstituted (C6-C30)aryl; a substituted or unsubstituted (3- to 30-membered)heteroaryl containing at least one of nitrogen(s), oxygen(s), and sulfur(s); or a substituted or unsubstituted di(C6-C30)arylamino;

L 1 and L 2 , each independently, represent a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (3- to 30-membered)heteroarylene; and

n represents an integer of 0 or 1, with the proviso that if n is 0, both ring A and ring B are a substituted or unsubstituted naphthalene ring;

wherein,

Ar 1 and Ar 22 , each independently, represent a phenyl unsubstituted or substituted with deuterium(s), a biphenyl unsubstituted or substituted with deuterium(s), a terphenyl unsubstituted or substituted with deuterium(s), or a naphthyl unsubstituted or substituted with deuterium(s);

L 21 represents a naphthylene unsubstituted or substituted with deuterium(s), or a biphenylene unsubstituted or substituted with deuterium(s);

R 1 , R 4 , R 5 , and R 8 , each independently, represent hydrogen, deuterium, a phenyl unsubstituted or substituted with deuterium(s), a biphenyl unsubstituted or substituted with deuterium(s), a terphenyl unsubstituted or substituted with deuterium(s), or a naphthyl unsubstituted or substituted with deuterium(s); and

R 2 , R 3 , R 6 , and R 7 , each independently, represent hydrogen or deuterium;

with the proviso that if both Ar 21 and Ar 22 represent phenyl, at least one of R 1 , R 4 , R 5 , and R 8 is not hydrogen or deuterium.

2. The plurality of host materials according to claim 1 , wherein the substituents of the substituted benzene, the substituted naphthalene, the substituted aryl, the substituted arylene, the substituted heteroaryl, the substituted heteroarylene, and diarylamino, 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 (3- to 50-membered)heteroaryl unsubstituted or substituted with at least one of a (C1-C30)alkyl(s), a (C6-C30)aryl(s), and a di(C6-C30)arylamino(s); a (C6-C30)aryl unsubstituted or substituted with at least one of deuterium(s), a cyano(s), a (C1-C30)alkyl(s), a (3- to 50-membered)heteroaryl(s), a di(C6-C30)arylamino(s), and a tri(C6-C30)arylsilyl(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; 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 plurality of host materials according to claim 1 , wherein the formula 1 is represented by any one of the following formulas 1-1 to 1-7:

wherein,

Ar 1 , L 1 , and Y are as defined in claim 1 ;

R 11 to R 27 , 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 (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; and

a, d, h, m, q, and r, each independently, represent an integer of 1 to 6; and b, c, e, f, g, i, j, k, I, o, and p, each independently, represent an integer of 1 to 4, in which if a to m and o to r, each independently, are an integer of 2 or more, each of R 11 , each of R 12 , each of R 13 , each of R 14 , each of R 15 , each of R 16 , each of R 17 , each of R 18 , each of R 19 , each of R 20 , each of R 21 , each of R 22 , each of R 23 , each of R 24 , each of R 25 , each of R 26 , and each of R 27 may be the same or different.

4. The plurality of host materials according to claim 1 , wherein Ar 1 represents a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted benzofuropyrimidinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted benzoquinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted benzoquinoxalinyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted benzocarbazolyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzothiophenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted naphthyridinyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted benzofluorenyl, a substituted or unsubstituted spirobifluorenyl, a substituted or unsubstituted triphenylenyl, a substituted or unsubstituted benzonaphthofuranyl, a substituted or unsubstituted benzonaphthothiophenyl, a substituted or unsubstituted diphenylamino, a substituted or unsubstituted naphthylphenylamino, or a substituted or unsubstituted biphenylphenylamino.

5. The plurality of host materials according to claim 1 , wherein the compound represented by formula 1 is at least one selected from the following compounds:

6. The plurality of host materials according to claim 1 , wherein the compound represented by formul 3 is at least one selected from the following compounds:

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 at least one layer of the light-emitting layers comprises the plurality of host materials according to claim 1 .

Assignments (3)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 5, 2025
From: JUNG, SO-YOUNG; LEE, SU-HYUN; LEE, MI-JA; MOON, DOO-HYEON; CHO, SANG-HEE
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
Reel/Frame 070114/0101 →
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 11, 2023
From: JUNG, SO-YOUNG; LEE, MI-JA; LEE, SU-HYUN; MOON, DOO-HYEON; CHO, SANG HEE
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
Reel/Frame 063609/0272 →