IP Library Granted Patent US 11,793,075
Granted Patent B2
US 11,793,075 · App. 16/908,973 · Granted Oct 17, 2023

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); So-Young Jung (Gyeonggi-do, KR); Du-Yong Park (Gyeonggi-do, KR); Hae-Yeon Kim (Gyeonggi-do, KR); Sang-Hee Cho (Gyeonggi-do, KR); Jin-Ri Hong (Gyeonggi-do, KR)
H10K85/6576H10K85/622H10K85/631H10K85/654H10K85/656H10K85/6572H10K85/6574
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Quick Facts
Patent No.
US 11,793,075
App. No.
16/908,973
Granted
Oct 17, 2023
Kind
B2
Abstract

The present disclosure relates to a plurality of host materials and an organic electroluminescent device comprising the same. By comprising the host materials according to the present disclosure, an organic electroluminescent device having a high power efficiency and/or long lifespan can be provided.

Claims (70)

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 2:

wherein,

Y 1 represents O, S, CR 11 R 12 , or NR 13 ;

R 11 to R 13 each independently represent hydrogen, deuterium, halogen, 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, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; or R 11 and R 12 may be linked to each other to form a ring;

R 1 to R 3 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 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 (C1-C30)alkyl(C6-C30)arylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, a substituted or unsubstituted mono- or di- (3- to 30-membered)heteroarylamino, or a substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino; or may be linked to an adjacent substituent to form a ring;

provided that at least one of R 13 , R 2 , and R 3 represent(s) -L 1 -(Ar 1 ) d ;

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

Ar 1 each independently represent(s) a substituted or unsubstituted (3- to 30-membered)heteroaryl containing at least one nitrogen (N);

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

when a to d are equal to 2 or more, each R 1 , each R 2 , each R 3 , and each Ar 1 may be the same or different,

wherein,

X 21 and Y 21 each independently represent —N═, —NR 24 —, —O—, or —S—, provided that one of X 21 and Y 21 represents —N═, and the other represents —NR 24 —, —O—, or —S—;

R 21 represents a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3- to 30-membered)heteroaryl;

R 22 to R 24 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 fused ring of (C3-C30)aliphatic ring and (C6-C30)aromatic ring, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, a substituted or unsubstituted mono- or di- (3- to 30-membered)heteroarylamino, or a substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino; or may be linked to an adjacent substituent to form a ring;

provided that at least one of R 22 and R 23 represent(s) -L 21 -Ar 21 ;

L 21 represents a single bond or a substituted or unsubstituted (C6-C30)arylene;

Ar 21 represents a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted o-biphenyl, a substituted or unsubstituted m-biphenyl, a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted o-terphenyl, a substituted or unsubstituted m-terphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted triphenylenyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted chrysenyl, a substituted or unsubstituted fluoranthenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted benzofluorenyl, a substituted or unsubstituted spirobifluorenyl, a substituted or unsubstituted spiro[cyclopentane-fluorene]yl, a substituted or unsubstituted spiro[dihydroindene-fluorene]yl, a substituted or unsubstituted spiro[benzofluorene-fluorene]yl, 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, or an amino substituted with at least one of phenyl, naphthyl, naphthylphenyl, phenylnaphthyl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl, p-terphenyl, fluorenyl, benzofluorenyl, phenanthrenyl, benzonaphthofuranyl, dibenzothiophenyl, and dibenzofuranyl

f represents an integer of 1 or 2, q represents an integer of 1 to 4; and

when f and g are equal to 2 or more, each R 22 and each R 23 may be the same or different.

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

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

4. An organic electroluminescent device comprising: an anode; a cathode; and at least one light-emitting layer(s) between the anode and the cathode, wherein at least one light-emitting layer(s) comprise(s) 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 2:

wherein,

Y 1 represents O, S, CR 11 R 12 , or NR 13 ;

R 11 to R 13 each independently represent hydrogen, deuterium, halogen, 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, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; or R 11 and R 12 may be linked to each other to form a ring;

R 1 to R 3 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 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 (C1-C30)alkyl(C6-C30)arylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, a substituted or unsubstituted mono- or di- (3- to 30-membered)heteroarylamino, or a substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino; or may be linked to an adjacent substituent to form a ring;

provided that at least one of R 13 , R 2 , and R 3 represent(s) -L 1 -(Ar 1 ) d ;

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

Ar 1 each independently represent(s) a substituted or unsubstituted (3- to 30-membered)heteroaryl containing at least one nitrogen (N);

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

when a to d are equal to 2 or more, each R 1 , each R 2 , each R 3 , and each Ar 1 may be the same or different,

wherein,

X 21 and Y 21 each independently represent —N═, —NR 24 —, —O—, or —S—, provided that one of X 21 and Y 21 represents —N═, and the other represents —NR 24 —, —O—, or —S—;

R 21 represents a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3- to 30-membered)heteroaryl;

R 22 to R 24 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 fused ring of (C3-C30)aliphatic ring and (C6-C30)aromatic ring, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, a substituted or unsubstituted mono- or di- (3- to 30-membered)heteroarylamino, or a substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino; or may be linked to an adjacent substituent to form a ring;

provided that at least one of R 22 and R 23 represent(s) -L 21 -Ar 21 ;

L 21 represents a single bond or a substituted or unsubstituted (C6-C30)arylene;

Ar 21 represents a substituted or unsubstituted (C6-C30)aryl, a substituted or unsubstituted (3- to 30-membered)heteroaryl, a substituted or unsubstituted fused ring of (C3-C30)aliphatic ring and (C6-C30)aromatic ring, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, a substituted or unsubstituted mono- or di- (3- to 30-membered)heteroarylamino, or a substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino;

f represents an integer of 1 or 2, g represents an integer of 1 to 4; and

when f and g are equal to 2 or more, each R 22 and each R 23 may be the same or different.

5. An organic electroluminescent compound represented by the following formula 3-1:

wherein,

X 21 and Y 21 each independently represent —N═, —NR 24 —, —O—, or —S—, provided that one of X 21 and Y 21 represents —N═, and the other represents —NR 24 —, —O—, or —S—;

R 21 represents a substituted or unsubstituted (C6-C30)aryl or a substituted or unsubstituted (3- to 30-membered)heteroaryl;

R 22 to R 24 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 fused ring of (C3-C30)aliphatic ring and (C6-C30)aromatic ring, a substituted or unsubstituted mono- or di- (C1-C30)alkylamino, a substituted or unsubstituted mono- or di- (C6-C30)arylamino, a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, a substituted or unsubstituted mono- or di- (3- to 30-membered)heteroarylamino, or a substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino; or may be linked to an adjacent substituent to form a ring;

R 26 represents 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, a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, a substituted or unsubstituted mono- or di- (3- to 30-membered)heteroarylamino, or a substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino; or may be linked to an adjacent substituent to form a ring;

f represents an integer of 1 or 2;

when f is equal to 2 or more, each R 22 may be the same or different;

g′ represents an integer of 1 or 2, and i′ represents an integer of 1 to 4;

when g′ and i′ are equal to 2 or more, each R 23 , and each R 26 may be the same or different;

L 21 represents a single bond or a substituted or unsubstituted (C6-C30)arylene;

R 31 and R 32 each independently represent 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, or a substituted or unsubstituted (3- to 30-membered)heteroaryl; provided that at least one of R 31 and R 32 represent(s) a substituted or unsubstituted (3- to 30-membered)heteroaryl.

6. The organic electroluminescent compound according to claim 5 , wherein the compound represented by formula 3-1 is selected from the group consisting of:

7. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 6 .

8. The organic electroluminescent device according to claim 7 , wherein the organic electroluminescent compound is contained in a hole transport zone and/or a light-emitting layer.

9. The organic electroluminescent device according to claim 4 , wherein the formula 1 is represented by any one of the following formulas 1-1 to 1-9:

wherein,

Y 1 , L 1 , Ar 1 , R 1 to R 3 , and a to d are as defined in claim 5 ;

R 4 each independently is as defined as R 3 ; and

e represents an integer of 1 to 3, when e is equal to 2 or more, each R 4 may be the same or different.

10. The organic electroluminescent device according to claim 4 , wherein the formula 2 is represented by any one of the following formulas 2-1 to 2-5:

wherein,

X 21 , Y 21 , L 21 , Ar 21 , R 21 to R 23 , f, and g are as defined in claim 5 ;

R 25 and R 26 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, a substituted or unsubstituted (C1-C30)alkyl(C6-C30)arylamino, a substituted or unsubstituted mono- or di- (3- to 30-membered)heteroarylamino, or a substituted or unsubstituted (C6-C30)aryl(3- to 30-membered)heteroarylamino; or may be linked to an adjacent substituent to form a ring;

g′ represents an integer of 1 or 2, h and i each independently represent an integer of 1 to 3, and i′ represents an integer of 1 to 4; and

when g′, h, i, and i′ are equal to 2 or more, each R 23 , each R 25 , and each R 26 may be the same or different.

11. The organic electroluminescent device according to claim 4 , wherein Ar 1 each independently represent(s) a substituted or unsubstituted pyridyl, a substituted or unsubstituted pyrimidinyl, a substituted or unsubstituted triazinyl, a substituted or unsubstituted pyrazinyl, a substituted or unsubstituted pyridazinyl, 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.

12. The organic electroluminescent device according to claim 4 , wherein Ar 21 represents a substituted or unsubstituted phenyl, a substituted or unsubstituted naphthyl, a substituted or unsubstituted o-biphenyl, a substituted or unsubstituted m-biphenyl, a substituted or unsubstituted p-biphenyl, a substituted or unsubstituted o-terphenyl, a substituted or unsubstituted m-terphenyl, a substituted or unsubstituted p-terphenyl, a substituted or unsubstituted triphenylenyl, a substituted or unsubstituted phenanthrenyl, a substituted or unsubstituted chrysenyl, a substituted or unsubstituted fluoranthenyl, a substituted or unsubstituted fluorenyl, a substituted or unsubstituted benzofluorenyl, a substituted or unsubstituted spirobifluorenyl, a substituted or unsubstituted spiro[cyclopentane-fluorene]yl, a substituted or unsubstituted spiro[dihydroindene-fluorene]yl, a substituted or unsubstituted spiro[benzofluorene-fluorene]yl, 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, or an amino substituted with at least one of phenyl, naphthyl, naphthylphenyl, phenylnaphthyl, o-biphenyl, m-biphenyl, p-biphenyl, o-terphenyl, m-terphenyl, p-terphenyl, fluorenyl, benzofluorenyl, phenanthrenyl, benzonaphthofuranyl, dibenzothiophenyl, and dibenzofuranyl.

13. The organic electroluminescent device according to claim 4 , wherein the compound represented by formula 1 is selected from the group consisting of:

14. The organic electroluminescent device according to claim 4 , wherein the compound represented by formula 2 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 Jun 29, 2023
From: KIM, BITNARI; LEE, SU-HYUN; MOON, DOO-HYEON; JUNG, SO-YOUNG; PARK, DU-YONG; KIM, HAE-YEON; CHO, SANG-HEE; HONG, JIN-RI
To: ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.
Reel/Frame 064108/0184 →