IP Library Granted Patent US 12,049,468
Granted Patent B2
US 12,049,468 · App. 16/972,962 · Granted Jul 30, 2024

Plurality of host materials and organic electroluminescent device comprising the same

Inventors: Bitnari Kim (Gyeonggi-do, KR); Su-Hyun Lee (Gyeonggi-do, KR); Doo-Hyeon Moon (Gyeonggi-do, KR); Hyo-Soon Park (Gyeonggi-do, KR); Tae-Jun Han (Gyeonggi-do, KR); Sang-Hee Cho (Gyeonggi-do, KR)
Assignee: Rohm and Haas Electronic Materials Korea Ltd.
C07D487/06H10K85/6572H10K85/6574H10K2101/90
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Quick Facts
Patent No.
US 12,049,468
App. No.
16/972,962
Granted
Jul 30, 2024
Kind
B2
Abstract

The present disclosure relates to a plurality of host materials comprising a compound represented by formula 1 and a compound represented by formula 2, and an organic electroluminescent device comprising the same. By comprising the plurality of host materials comprising a specific combination of compounds, it is possible to provide an organic electroluminescent device having long lifespan characteristics.

Claims (40)

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

wherein

X 1 to X 13 each independently represent N or CR 1 ;

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

Ar represents 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, —NR 5 R 6 , or —SiR 7 R 8 R 9 ; or may be linked to an adjacent substituent to form a ring;

R 1 represents -L 1 -(Ar) a , 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, —NR 5 R 6 , or —SiR 7 R 8 R 9 ; or may be linked to one pair selected from X 1 and X 2 , X 2 and X 3 , X 3 and X 4 , X 5 and X 6 , X 6 and X 7 , X 8 and X 9 , X 10 and X 11 , X 11 and X 12 , and X 12 and X 13 , as a pair of an adjacent substituent to form a ring;

R 5 to R 9 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;

a represents an integer of 1 to 3, where if a is an integer of 2 or more, each of Ar may be the same or different;

wherein

HAr represents a substituted or unsubstituted (3- to 30-membered)heteroaryl;

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

R 21 and R 22 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, —NR 5 R 6 , or —SiR 7 R 8 R 9 ; or may be linked to an adjacent substituent to form a ring, with a proviso that at least one of two adjacent R 21 's or two adjacent R 22 's are linked to each other to form a ring; and

b represents an integer of 1 to 4, c represents an integer of 1 to 6, where if b and c are an integer of 2 or more, each of R 21 and each of R 22 may be the same or different.

2. The plurality of host materials according to claim 1 , wherein formula 1 is represented by the following formula 1-1:

wherein

L 1 represents a single bond, or a substituted or unsubstituted (C6-C30)arylene;

Ar represents hydrogen, deuterium, a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, or —NR 5 R 6 ;

R 5 and R 6 each independently represent a substituted or unsubstituted (C1-C30)alkyl, a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl;

R 11 to R 14 each independently are identical to the definition of R 1 in claim 1 ; and

aa represents an integer of 1 to 3, ab and ac each independently represent an integer of 1 to 4, ad represents 1 or 2, where if aa, ab, ac, and ad are an integer of 2 or more, each of R 11 , each of R 12 , each of R 13 , and each of R 14 may be the same or different.

3. The plurality of host materials according to claim 1 , wherein in formula 1, Ar represents a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted biphenyl, a substituted or unsubstituted naphthylphenyl, a substituted or unsubstituted phenylnaphthyl, a substituted or unsubstituted terphenyl, a substituted or unsubstituted carbazolyl, a substituted or unsubstituted benzocarbazolyl, a substituted or unsubstituted dibenzocarbazolyl, a substituted or unsubstituted dibenzothiophenyl, a substituted or unsubstituted benzothiophenyl, a substituted or unsubstituted benzonaphthothiophenyl, a substituted or unsubstituted dibenzofuranyl, a substituted or unsubstituted benzofuranyl, a substituted or unsubstituted benzonaphthofuranyl, a substituted or unsubstituted naphthyridinyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted benzofluorenyl, a substituted or unsubstituted diphenylamino, a substituted or unsubstituted phenylbiphenylamino, a substituted or unsubstituted naphthylbiphenylamino, a substituted or unsubstituted dibiphenylamino, a substituted or unsubstituted biphenylfluorenylamino, or a substituted or unsubstituted biphenyldibenzofuranylamino.

4. The plurality of host materials according to claim 1 , wherein formula 2 is represented by at least one of the following formulas 2-1 to 2-6:

wherein

HAr and L 2 are as defined in claim 1 ;

R 31 to R 44 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, —NR 5 R 6 , or —SiR 7 R 8 R 9 ; or may be linked to an adjacent substituent to form a ring;

V and W each independently represent NR 16 , O, or S;

R 16 represents a substituted or unsubstituted (C6-C30)aryl, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; and

d, h, i, j, l, n, o, p, and q each independently represent an integer of 1 to 4, e, f, g, k, and m each independently represent an integer of 1 to 6, where if d to q are an integer of 2 or more, each of R 31 to each of R 44 may be the same or different.

5. The plurality of host materials according to claim 1 , wherein in formula 2, HAr represents a substituted or unsubstituted triazinyl, a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted quinazolinyl, a substituted or unsubstituted benzoquinazolinyl, a substituted or unsubstituted quinoxalinyl, a substituted or unsubstituted benzoquinoxalinyl, a substituted or unsubstituted quinolyl, a substituted or unsubstituted benzoquinolyl, a substituted or unsubstituted isoquinolyl, a substituted or unsubstituted benzoisoquinolyl, a substituted or unsubstituted triazolyl, a substituted or unsubstituted pyrazolyl, a substituted or unsubstituted naphthyridinyl, or a substituted or unsubstituted benzothienopyrimidinyl.

6. The plurality of host materials according to claim 1 , wherein formula 1 is represented by at least one of the following formulas 1-11 to 1-40:

wherein

L 1 represents a single bond, or is represented by one of the following formulas L 1 -1 to L 1 -7, and

Ar is represented by one of the following formulas Ar-1 to Ar-121:

7. The plurality of host materials according to claim 1 , wherein formula 2 is represented by at least one of the following formulas 2-11 to 2-38:

wherein

HAr is represented by one of the following formulas 2-40 to 2-58, and

L 2 is represented by one of the following formulas 3-1 to 3-47:

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

9. The plurality of host materials according to claim 1 , wherein the compound represented by formula 2 is selected from the following compounds:

10. An organic electroluminescent device comprising an anode, a cathode, and at least one light-emitting layer between the anode and the cathode, wherein at least one layer of the light-emitting layers comprises the plurality of host materials 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 20, 2024
From: KIM, BITNARI; MOON, DOO-HYEON; HAN, TAE-JUN; LEE, SU-HYUN; PARK, HYO-SOON; CHO, SANG-HEE
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
Reel/Frame 067459/0829 →