IP Library › Granted Patent US 11,616,202
Granted Patent B2
US 11,616,202 · App. 16/419,723 · Granted Mar 28, 2023

Compound, composition and organic optoelectronic device and display device

Inventors: Seungjae Lee (Suwon-si, KR); Changwoo Kim (Suwon-si, KR); Byungku Kim (Suwon-si, KR); Hyung Sun Kim (Suwon-si, KR); Dong Wan Ryu (Suwon-si, KR); Chang Ju Shin (Suwon-si, KR); Kipo Jang (Suwon-si, KR); Min Seok Seo (Suwon-si, KR); Sung-Hyun Jung (Suwon-si, KR)
Assignees: Samsung SDI Co., Ltd.; Samsung Electronics Co., Ltd.
H01L51/0072C07D405/14C09K11/02C09K11/06H01L51/0067H01L51/0073C09K2211/1007C09K2211/1029C09K2211/185H01L51/5012H01L51/5016
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Quick Facts
Patent No.
US 11,616,202
App. No.
16/419,723
Granted
Mar 28, 2023
Kind
B2
Abstract

A compound represented by a combination of Chemical Formula 1 and Chemical Formula 2 bonded together, a composition including the compound, an organic optoelectronic device, and a display device are disclosed. In Chemical Formula 1 and Chemical Formula 2, each substituent is the same as described in the specification.

Claims (56)

1. A compound represented by a combination of Chemical Formula 1 and Chemical Formula 2 bonded together:

wherein, in Chemical Formula 1 and Chemical Formula 2,

X is O or S,

Z is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted phenyl group,

L 1 and L 2 are each independently a single bond, or a substituted or unsubstituted C6 to C20 arylene group,

one of a* and b* of Chemical Formula 1 is a bond with c* of Chemical Formula 2, and the other of a* and b* is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group, and

R 1 to R 7 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group.

2. The compound as claimed in claim 1 , which is represented by Chemical Formula 1A or Chemical Formula 1B:

wherein, in Chemical Formula 1A and Chemical Formula 1B,

X is O or S,

Z is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted phenyl group,

L 1 and L 2 are each independently a single bond, or a substituted or unsubstituted C6 to C20 arylene group, and

R a , R b , and R 1 to R 7 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group.

3. The compound as claimed in claim 2 , which is represented by one of Chemical Formula 1A-1 to Chemical Formula 1A-4 and Chemical Formula 1B-1 to 1B-3:

wherein, in Chemical Formula 1A-1 to Chemical Formula 1A-4, and Chemical Formula 1B-1 to Chemical Formula 1B-3,

X is O or S,

Z is hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted phenyl group,

L 1 and L 2 are each independently a single bond, or a substituted or unsubstituted C6 to C20 arylene group, and

R a , R b and R 1 to R 7 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group.

4. The compound as claimed in claim 3 , the compound being represented by Chemical Formula 1A-3 or Chemical Formula 1B-2.

5. The compound as claimed in claim 1 , wherein R 7 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted anthracenyl group, a substituted or unsubstituted phenanthrenyl group, or a substituted or unsubstituted triphenylenyl group.

6. The compound as claimed in claim 1 , the compound being selected from compounds of Group 1:

7. A composition, comprising:

the first compound represented by the combination of Chemical Formula 1 and Chemical Formula 2 bonded together as claimed in claim 1 , and

a second compound represented by Chemical Formula 3:

wherein, in Chemical Formula 3,

Y 1 and Y 2 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group,

R c and R 8 to R 13 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a cyano group, or a combination thereof, and

m is 0, 1, or 2.

8. The composition as claimed in claim 7 , wherein Chemical Formula 3 is represented by Chemical Formula 3A:

wherein, in Chemical Formula 3A,

Y 1 and Y 2 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,

Ar 1 and Ar 2 are each independently a substituted or unsubstituted C6 to C20 aryl group or a substituted or unsubstituted C2 to C30 heterocyclic group, and

R 8 to R 13 are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, a cyano group, or a combination thereof.

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

Chemical Formula 3 is one of structures of Group II, and

—Y 1 —Ar 1 and *—Y 2 —Ar 2 are one of Group III:

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

10. The composition as claimed in claim 9 , wherein:

Chemical Formula 3 is represented by Chemical Formula C-8 or Chemical Formula C-17 of Group II, and

—Y 1 —Ar 1 and *—Y 2 —Ar 2 are one of Group III.

11. An organic optoelectronic device, comprising:

an anode and a cathode facing each other,

at least one organic layer disposed between the anode and the cathode, wherein the organic layer includes the composition as claimed in claim 7 .

12. The organic optoelectronic device as claimed in claim 11 , wherein:

the organic layer includes a light emitting layer, and

the light emitting layer includes the composition.

13. A display device comprising the organic optoelectronic device as claimed in claim 11 .

14. An organic optoelectronic device, comprising:

an anode and a cathode facing each other,

at least one organic layer disposed between the anode and the cathode, wherein the organic layer includes the compound as claimed in claim 1 .

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

the organic layer includes a light emitting layer, and

the light emitting layer includes the compound.

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

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 19, 2019
From: SAMSUNG SDI CO., LTD.; SAMSUNG ELECTRONICS CO., LTD.
To: SAMSUNG SDI CO., LTD.; SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 051338/0532 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 22, 2019
From: LEE, SEUNGJAE; KIM, CHANGWOO; KIM, BYUNGKU; KIM, HYUNG SUN; RYU, DONG WAN; SHIN, CHANG JU; JANG, KIPO; SEO, MIN SEOK; JUNG, SUNG-HYUN
To: SAMSUNG SDI CO., LTD.; SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 049257/0400 →
Priority Claims (1)
KR 10-2018-0060520 · May 28, 2018 · national
Continuity (1)
Related Publication 20190363261A1 · Nov 28, 2019
Cited By (1)
US 12,421,247