IP Library Granted Patent US 12698275
Granted Patent B2
US 12698275 · App. 17/965,074 · Granted Aug 4, 2026

Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device and display device

Inventors: Jiyun Kwon (Suwon-si, KR); Dong Min Kang (Suwon-si, KR); Byungku Kim (Suwon-si, KR); Jin Sook Kim (Suwon-si, KR); Byoungkwan Lee (Suwon-si, KR); Kipo Jang (Suwon-si, KR); Suyong Lim (Suwon-si, KR); Sung-Hyun Jung (Suwon-si, KR); Ho Kuk Jung (Suwon-si, KR)
Assignee: SAMSUNG SDI CO., LTD.
C07D405/04C07D405/14C07D409/14C07D413/14C07D417/14C07F7/0812H10K50/12H10K85/40H10K85/615H10K85/622H10K85/652H10K85/654H10K85/657H10K85/6572H10K85/6574H10K85/6576C07B2200/05
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Quick Facts
Patent No.
US 12698275
App. No.
17/965,074
Granted
Aug 4, 2026
Kind
B2
Abstract

A compound for an organic optoelectronic device, a composition for an organic optoelectronic device including the same, an organic optoelectronic device, and a display device, the compound being represented by Chemical Formula 1:

Claims (96)

1 . A composition for an organic optoelectronic device, the composition comprising:

a first compound; and

a second compound,

wherein:

the first compound is represented by Chemical Formula 1, and

the second compound is represented by Chemical Formula 2:

wherein, in Chemical Formula 1,

X 1 is O or S,

Z 1 to Z 3 are each independently N or CR a , at least two of Z 1 to Z 3 being N,

L 1 and L 2 are each independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

L 3 is a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C30 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

R a and R 1 to R 5 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,

m1 and m4 are each independently an integer of 1 to 3,

m2 is 1 or 2, and

m3 and m5 are each independently an integer of 1 to 4,

in Chemical Formula 2,

X 2 is O, S, NR b , CR c R d , or SiR e R f ,

R b , R c , R d , R e , R f and R 6 are each independently hydrogen, deuterium, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

m6 is an integer of 1 to 4, and

ring A is a ring of Group II,

in Group II,

* is a linking point,

X 3 is O, S, NR g , CR h R i , or SiR j R k ,

R g , R h , R i , R j , R k , and R 7 to R 11 are each independently hydrogen, deuterium, a substituted or unsubstituted amine group, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

m7, m9, and m11 are each independently an integer of 1 to 4,

m8 and m10 are each independently 1 or 2, and

at least one of R 6 to R 11 is a group represented by Chemical Formula a,

in Chemical Formula a,

L 4 to L 6 are each independently a single bond or a substituted or unsubstituted C6 to C30 arylene group,

Ar 3 and Ar 4 are each independently a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and

* is a linking point.

2 . The composition as claimed in claim 1 , wherein:

Chemical Formula 1 is represented by Chemical Formula 1A-1 or Chemical Formula 1A-2:

in Chemical Formula 1A-1 and Chemical Formula 1A-2, X 1 , Z 1 to Z 3 , L 1 to L 3 , Ar 1 , Ar 2 , R 1 to R 5 , m1, and m3 to m5 are defined the same as those of Chemical Formula 1.

3 . The composition as claimed in claim 1 , wherein:

Chemical Formula 1 is represented by Chemical Formula 1A-1-1, Chemical Formula 1A-1-2, Chemical Formula 1A-2-1, or Chemical Formula 1A-2-2:

in Chemical Formula 1A-1-1, Chemical Formula 1A-1-2, Chemical Formula 1A-2-1, and Chemical Formula 1A-2-2, X 1 , Z 1 to Z 3 , L 1 to L 3 , Ar 1 , Ar 2 , R 1 to R 5 , m1, and m3 to m5 are defined the same as those of Chemical Formula 1.

4 . The composition as claimed in claim 1 , wherein:

Chemical Formula 1 is represented by one of Chemical Formula 1B-1 to Chemical Formula 1B-4:

in Chemical Formula 1B-1 to Chemical Formula 1B-4,

X 1 , Z 1 to Z 3 , L 1 to L 3 , Ar 1 , Ar 2 , R 1 to R 5 , m1, m2, m4, and m5 are defined the same as those of Chemical Formula 1, and

m3 is an integer of 1 to 3.

5 . The composition as claimed in claim 1 , wherein:

Chemical Formula 1 is represented by Chemical Formula 1B-1-1, Chemical Formula 1B-1-2, Chemical Formula 1B-2-1, Chemical Formula 1B-2-2, Chemical Formula 1B-3-1, Chemical Formula 1B-3-2, Chemical Formula 1B-4-1, or Chemical Formula 1B-4-2:

in Chemical Formula 1B-1-1, Chemical Formula 1B-1-2, Chemical Formula 1B-2-1, Chemical Formula 1B-2-2, Chemical Formula 1B-3-1, Chemical Formula 1B-3-2, Chemical Formula 1B-4-1, and Chemical Formula 1B-4-2,

X 1 , Z 1 to Z 3 , L 1 to L 3 , Ar 1 , Ar 2 , R 1 to R 5 , m1, m2, m4, and m5 are defined the same as those of Chemical Formula 1, and

m3 is an integer of 1 to 3.

6 . The composition as claimed in claim 1 , wherein Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted acridinyl group, a substituted or unsubstituted xanthenyl group, substituted or unsubstituted 10-phenyl-10H-spiro [acridine-9,9′-fluorenyl group], a substituted or unsubstituted 10H-spiro[acridine-9,9′-fluorenyl group], a substituted or unsubstituted spiro[fluorene-9,9′-xanthenyl group], a substituted or unsubstituted dibenzosilolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted benzonaphthofuranyl group, a substituted or unsubstituted benzonaphthothiophenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted dibenzocarbazolyl group, a substituted or unsubstituted dinaphthofuranyl group, a substituted or unsubstituted dinaphthothiophenyl group, a substituted or unsubstituted benzofuranofluorenyl group, a substituted or unsubstituted benzothiophenofluorenyl group, a substituted or unsubstituted phenoxazinyl group, a substituted or unsubstituted thiophenoxazinyl group, a substituted or unsubstituted benzophenoxazinyl group, or a substituted or unsubstituted benzothiophenoxazinyl group.

7 . The composition as claimed in claim 1 , wherein:

L 1 and L 2 are each independently a single bond, a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group, and

L 3 is a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted anthracenylene group, a substituted or unsubstituted phenanthrenylene group, a substituted or unsubstituted dibenzofuranylene group, or a substituted or unsubstituted dibenzothiophenylene group.

8 . The composition as claimed in claim 1 , wherein:

moieties *-L 1 -Ar 1 and *-L 2 -Ar 2 are each independently a moiety of Group I:

in Group I, * is a linking point.

9 . The composition as claimed in claim 1 ,

wherein the first compound is a compound of Group 1:

10 . The composition as claimed in claim 1 wherein:

Chemical Formula 2 is represented by one of Chemical Formula 2-I to Chemical Formula 2-IX:

in Chemical Formula 2-I to Chemical Formula 2-IX, X 2 , X 3 , m6 to m11, and R 6 to R 11 are defined the same as those of Chemical Formula 2.

11 . The composition as claimed in claim 10 , wherein:

the second compound is represented by one of Chemical Formula 2-IA to Chemical Formula 2-IXA, Chemical Formula 2-IB to Chemical Formula 2-IXB, and Chemical Formula 2-IIC to Chemical Formula 2-IVC:

in Chemical Formula 2-IA to Chemical Formula 2-IXA, Chemical Formula 2-IB to Chemical Formula 2-IXB, and Chemical Formula 2-IIC to Chemical Formula 2-IVC,

X 2 , X 3 , L 4 to L 6 , m6 to m11, Ar 3 and Ar 4 are defined the same as those of Chemical Formula 2,

R 6 to R 11 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,

m6′, m7′, m9′, and m11′ are each independently an integer of 1 to 3, and

m8′ is 1.

12 . The composition as claimed in claim 10 , wherein:

the second compound is represented by Chemical Formula 2-IVB-2 or Chemical Formula 2-VIIIB-2:

0 in Chemical Formula 2-IVB-2 and Chemical Formula 2-VIIIB-2,

L 4 to L 6 are each independently a single bond or a substituted or unsubstituted phenylene group,

Ar 3 and Ar 4 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted naphthyl group,

X 2 is NR b , O, or S,

X 3 is CR h R i or SiR j R k ,

R b , R h , R i , R j , and R k are each independently a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group,

R 6 , R 8 , R 9 , R 10 , and R 11 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,

m6 is an integer of 1 to 4,

m8 and m10 are each independently 1 or 2, and

m9′ and m11′ are each independently an integer of 1 to 3.

13 . An organic optoelectronic device, comprising:

an anode and a cathode facing each other, and

at least one organic layer between the anode and the cathode,

wherein:

the at least one organic layer includes a light emitting layer, and

the light emitting layer includes the composition for the organic optoelectronic device as claimed in claim 1 .

14 . The organic optoelectronic device as claimed in claim 13 , wherein the composition for the organic optoelectronic device is a host of the light emitting layer.

15 . A display device comprising the organic optoelectronic device as claimed in claim 13 .

16 . A compound for an organic optoelectronic device, wherein the compound is a compound of Group 1:

17 . An organic optoelectronic device, comprising:

an anode and a cathode facing each other, and

at least one organic layer between the anode and the cathode,

wherein:

the at least one organic layer includes a light emitting layer, and

the light emitting layer includes the compound for the organic optoelectronic device as claimed in claim 16 .

18 . The organic optoelectronic device as claimed in claim 17 , wherein the compound for the organic optoelectronic device is a host of the light emitting layer.

19 . A display device comprising the organic optoelectronic device as claimed in claim 17 .