IP Library › Granted Patent US 12,274,160
Granted Patent B2
US 12,274,160 · App. 17/336,558 · Granted Apr 8, 2025

Composition for organic optoelectronic device and organic optoelectronic device and display device

Inventors: Jonghoon Kim (Suwon-si, KR); Youngmook Lim (Suwon-si, KR); Changwoo Kim (Suwon-si, KR); Hansol Seo (Suwon-si, KR); Hyung Sun Kim (Suwon-si, KR); Mijin Lee (Suwon-si, KR); Sung-Hyun Jung (Suwon-si, KR); Ho Kuk Jung (Suwon-si, KR); Youngkyoung Jo (Suwon-si, KR); Dalho Huh (Suwon-si, KR)
Assignee: SAMSUNG SDI CO., LTD.
H10K85/622H10K85/615H10K85/626H10K85/654H10K85/657H10K85/6572H10K85/6574H10K50/11H10K2101/10
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Quick Facts
Patent No.
US 12,274,160
App. No.
17/336,558
Granted
Apr 8, 2025
Kind
B2
Abstract

A composition for an organic optoelectronic device, an organic optoelectronic device, and a display device, the composition including a first compound represented by Chemical Formula I, a second compound represented by Chemical Formula II, and a third compound represented by Chemical Formula III,

Claims (94)

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

a first compound;

a second compound; and

a third compound,

wherein:

the first compound is represented by one of Chemical Formula I-A and Chemical Formula I-D to Chemical Formula I-I,

the second compound is represented by Chemical Formula II, and

the third compound is represented by Chemical Formula III:

wherein, in Chemical Formula I-A and Chemical Formula I-D to Chemical Formula I-I,

Z 1 to Z 3 is N or C-L a -R a , at least two of Z 1 to Z 3 being N,

L a and L 1 to L 3 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,

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

R a and R 3 to R 6 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof,

X 1 is O, S, or NR b , and

R b and R 7 to R 22 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof,

wherein, in Chemical Formula II,

L 4 is a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,

Ar 1 is a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof,

R 23 to R 26 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof, and

B is a group represented by one of Substituent B-1 to Substituent B-4:

wherein, in Substituent B-1 to Substituent B-4,

L 5 to L 7 are each independently a single bond, a substituted or unsubstituted C6 to C20 arylene group, a substituted or unsubstituted C2 to C20 heterocyclic group, or a combination thereof,

Ar 2 and Ar 3 are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof,

R 27 to R 38 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted silyl group, a substituted or unsubstituted amine group, a halogen, a cyano group, or a combination thereof, and

* is a linking carbon;

wherein, in Chemical Formula III,

R 39 to R 47 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, or a substituted or unsubstituted C6 to C30 aryl group,

L 8 is a substituted or unsubstituted C6 to C20 arylene group, and

Ar 4 is a substituted or unsubstituted C10 to C20 fused aryl group.

2. The composition as claimed in claim 1 , wherein the first compound is represented by Chemical Formula IA-1, Chemical Formula IA-4, or Chemical Formula IE-1:

wherein, in Chemical Formula IA-1, Chemical Formula IA-4, and Chemical Formula IE-1, Z 1 to Z 3 , L 1 to L 3 , R 1 , R 2 , R 5 , and X 1 are defined the same as those of Chemical Formula I-A and Chemical Formula I-D to Chemical Formula I-I.

3. The composition as claimed in claim 1 , wherein the second compound is represented by Chemical Formula IIA or Chemical Formula IIF:

wherein, in Chemical Formula IIA and Chemical Formula IIF, L 4 to L 7 , Ar 1 to Ar 3 , and R 23 to R 38 are defined the same as those of Chemical Formula II.

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

the second compound is represented by Chemical Formula IIA, and

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

wherein, in Chemical Formula IIA-1 and Chemical Formula IIA-2, L 4 , L 6 , Ar 1 , Ar 2 , and R 23 to R 32 are defined the same as those of Chemical Formula II.

5. The composition as claimed in claim 1 , wherein the third compound is represented by Chemical Formula III-1:

wherein, in Chemical Formula III-1, R 39 to R 47 , L 8 , and Ar 4 are defined the same as those of Chemical Formula III.

6. The composition as claimed in claim 5 , wherein L 8 is a substituted or unsubstituted phenylene group.

7. The composition as claimed in claim 5 , wherein L 8 is a linking group of Group I:

wherein, in Group I, * is a linking point.

8. The composition as claimed in claim 5 , wherein Ar 4 is a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted triphenylene group, or a substituted or unsubstituted perylenyl group.

9. The composition as claimed in claim 5 , wherein Ar 4 is a group of the following Group II:

wherein, in Group II, * is a linking point.

10. The composition as claimed in claim 1 , wherein the third compound is a compound of Group 3:

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

the first compound is represented by Chemical Formula IA-1 or Chemical Formula IA-4,

the second compound is represented by Chemical Formula IIA-1 or Chemical Formula IIA-2, and

the third compound is represented by Chemical Formula III-1:

wherein, in Chemical Formula IA-1 and Chemical Formula IA-4,

Z 1 to Z 3 are each N,

L 1 to L 3 are each independently a single bond or a substituted or unsubstituted phenylene group,

R 1 and R 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and

R 5 is a substituted or unsubstituted phenyl group;

wherein, in Chemical Formula IIA-1 and Chemical Formula IIA-2,

R 23 to R 32 are each hydrogen,

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

Ar 1 and Ar 2 are independently a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group; and

wherein, in Chemical Formula III-1,

R 39 to R 47 are each hydrogen,

L 8 is a substituted or unsubstituted meta-phenylene group, and

Ar 4 is a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylene group.

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

the first compound is represented by Chemical Formula IA-1 or Chemical Formula IA-4,

the second compound is represented by Chemical Formula IIF, and

the third compound is represented by Chemical Formula III-1:

wherein, in Chemical Formula IA-1 and Chemical Formula IA-4,

Z 1 to Z 3 are each N,

L 1 to L 3 are each independently a single bond or a substituted or unsubstituted phenylene group,

R 1 and R 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and

R 5 is a substituted or unsubstituted phenyl group;

wherein, in Chemical Formula IIF,

R 23 to R 26 and R 33 to R 38 are each hydrogen,

L 4 and L 7 are each independently a single bond or a substituted or unsubstituted phenylene group, and

Ar 1 and Ar 3 are each independently a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group;

wherein, in Chemical Formula III-1,

R 39 to R 47 are each hydrogen,

L 8 is a substituted or unsubstituted meta-phenylene group, and

Ar 4 is a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylene group.

13. The composition as claimed in claim 1 , wherein the composition for an organic optoelectronic device includes

the first compound in an amount of about 20 wt % to about 50 wt %,

the second compound in an amount of about 40 wt % to about 60 wt %, and

the third compound in an amount of about 5 wt % to about 25 wt %, all wt % being based on a total weight of the first compound, the second compound, and the third compound.

14. An organic optoelectronic device, comprising:

an anode and a cathode facing each other,

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

wherein the at least one organic layer includes the composition for an organic optoelectronic device as claimed in claim 1 .

15. The organic optoelectronic device as claimed in claim 14 , wherein:

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

the light emitting layer includes the composition.

16. The organic optoelectronic device as claimed in claim 15 , wherein the first compound, the second compound, and the third compound are phosphorescent hosts of the light emitting layer.

17. The organic optoelectronic device as claimed in claim 15 , wherein the composition is a green light emitting composition.

18. A display device comprising the organic optoelectronic device as claimed in claim 14 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 2, 2021
From: KIM, JONGHOON; LIM, YOUNGMOOK; KIM, CHANGWOO; SEO, HANSOL; KIM, HYUNG SUN; LEE, MIJIN; JUNG, SUNG-HYUN; JUNG, HO KUK; JO, YOUNGKYOUNG; HUH, DALHO
To: SAMSUNG SDI CO., LTD.
Reel/Frame 056450/0315 →
Priority Claims (1)
KR 10-2020-0066669 · Jun 2, 2020 · national
Continuity (1)
Related Publication 20210376245A1 · Dec 2, 2021
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Cited By (1)
US 12,660,500