IP Library Granted Patent US 12,004,420
Granted Patent B2
US 12,004,420 · App. 16/886,822 · Granted Jun 4, 2024

Organic electroluminescent compound and organic electroluminescent device comprising the same

Inventors: Doo-Hyeon Moon (Gyeonggi-do, KR); Su-Hyun Lee (Gyeonggi-do, KR); Jin-Ri Hong (Gyeonggi-do, KR); So-Young Jung (Gyeonggi-do, KR); Dong-Hyung Lee (Gyeonggi-do, KR); Sang-Hee Cho (Gyeonggi-do, KR)
Assignee: Rohm and Haas Electronic Materials Korea Ltd.
H10K85/654H10K85/622H10K85/633H10K85/6572H10K85/6574H10K85/6576
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Quick Facts
Patent No.
US 12,004,420
App. No.
16/886,822
Granted
Jun 4, 2024
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, an organic electroluminescent device having a low driving voltage and/or a high luminous efficiency and/or a long lifespan can be provided.

Claims (30)

1. A plurality of host materials comprising at least one first host material comprising an organic electroluminescent compound represented by the following formula 1-1 or 1-2 and at least one second host material, which is different from the first host material, wherein the second host material comprises the compound represented by the following formula 100:

wherein,

R 1 and R 2 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (C3-C30)heteroaryl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to an adjacent substituent to form a ring;

R 3 , R a and R b 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 (C3-C30)heteroaryl where the (C3-C30)heteroaryl group is selected from the group consisting of furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, imidazopyridinyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, azacarbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, indolizidinyl, acrylidinyl, silafluorenyl and germafluorenyl, 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;

L 1 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, a substituted or unsubstituted (3- to 30-membered)heteroarylene, or a substituted or unsubstituted (C3-C30)cycloalkylene;

ETU is selected from any one of the substituents listed in the following Group 1;

Ar 1 and Ar 2 each independently represent a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (C3-C30)heteroaryl X represents CR 11 R 12 , O, or S;

R 11 and R 12 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted C3-C30)heteroaryl, or a substituted or unsubstituted (C3-C30)cycloalkyl; or may be linked to an adjacent substituent to form a ring;

p represents an integer of 1 to 4, and when p is 2 or more, each R 3 may be the same or different;

r represents an integer of 1 or 2, when r is 2, each R a may be the same or different;

s represents an integer of 1 to 4, when s is 2 or more, each R b may be the same or different; and

with the proviso that the compounds represented by the following formulas I-1 to I-3:

wherein,

R 1 , R 2 , and L 1 are as defined in formula 1-1 and 1-2;

ETU 1 to ETU 3 are as defined as ETU in formula 1-1 and 1-2;

at least one of L 1 and ETU 1 include(s) triazine structure in formula I-1;

at least one of L 1 and ETU 2 include(s) pyridine structure, pyrimidine structure, or triazine structure in formula I-2; and

at least one of L 1 and ETU 3 include quinazoline structure in formula I-3, are excluded:

wherein,

V represents CX 11 X 12 , NX 13 , O or S;

L 100 represents a single bond, a substituted or unsubstituted (C6-C30)arylene, or a substituted or unsubstituted (C3-C30)heteroarylene;

Ar 100 represents a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (C3-C30)heteroaryl, or -NX 9 X 10 ;

X 9 and X 10 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C3-C30)cycloalkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (C3-C30)heteroaryl;

X 11 to X 13 , X 101 and X 102 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 (C3-C30)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-(C2-C30) alkenylamino, a substituted or unsubstituted (C1-C30)alkyl(C2-C30)alkenylamino, a substituted or unsubstituted mono- or di-(C6-C30)arylamino, a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, a substituted or unsubstituted (C2-C30)alkenyl(C6-C30)arylamino, a substituted or unsubstituted mono- or di-(C3-C30)heteroarylamino, a substituted or unsubstituted (C1-C30)alkyl(C3-C30)heteroarylamino, a substituted or unsubstituted (C2-C30)alkenyl(C3-C30)heteroarylamino, or a substituted or unsubstituted (C6-C30)aryl(C3-C30)heteroarylamino; and

j represents an integer of 1 to 4, k represents an integer of 1 to 6, and when j and k are 2 or more, each X 101 and each X 102 may be the same or different.

2. The plurality of host materials according to claim 1 , wherein Ar 1 and Ar 2 each independently are selected from any one of the substituents listed in the following Group 2.

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

4. An organic electroluminescent device comprising the plurality of host materials according to claim 1 .

5. The organic electroluminescent device according to claim 4 , wherein the organic electroluminescent compound is contained in a light-emitting layer and/or an electron transport zone.

6. The host materials according to claim 1 , wherein the compound represented by formula 100 is selected from the group consisting of:

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 29, 2024
From: MOON, DOO-HYEON; LEE, SU-HYUN; HONG, JIN-RI; JUNG, SO-YOUNG; LEE, DONG-HYUNG; CHO, SANG HEE
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
Reel/Frame 066943/0639 →
Priority Claims (2)
KR 10-2019-0078837 · Jul 1, 2019 · national
KR 10-2020-0051436 · Apr 28, 2020 · national
Continuity (1)
Related Publication 20210005822A1 · Jan 7, 2021