IP Library › Granted Patent US 11,844,271
Granted Patent B2
US 11,844,271 · App. 16/954,722 · Granted Dec 12, 2023

Organic compound, composition, organic optoelectronic device, and display apparatus

Inventors: Hanill Lee (Suwon-si, KR); Byungku Kim (Suwon-si, KR); Youngsung Park (Suwon-si, KR); Chang Ju Shin (Suwon-si, KR); Dongkyu Ryu (Suwon-si, KR); Seungjae Lee (Suwon-si, KR); Kipo Jang (Suwon-si, KR); Sung-Hyun Jung (Suwon-si, KR)
Assignees: SAMSUNG SDI CO., LTD.; SAMSUNG ELECTRONICS CO., LTD.
H10K85/654C07D209/86C07D405/14C07D409/14C07D487/04C09K11/025H10K85/6574H10K85/6576H10K50/11H10K2101/10
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Quick Facts
Patent No.
US 11,844,271
App. No.
16/954,722
Granted
Dec 12, 2023
Kind
B2
Abstract

The present invention relates to an organic compound represented by Chemical Formula 1, a composition, an organic optoelectronic device, and a display device.

Claims (71)

1. An organic compound represented by Chemical Formula 1A or Chemical Formula 1B:

wherein, in Chemical Formulae 1A and 1B,

Z 1 to Z 3 are independently N or CH,

at least two of Z 1 to Z 3 are N,

A 1 and Ar 2 are independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted pyridinyl group,

L is a single bond or a substituted or unsubstituted phenylene group,

X 1 and X 2 are independently O or S,

R 1 to R 8 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted phenyl group, or a cyano group, and

‘substituted’ refers to replacement of at least one hydrogen of a substituent by deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group, a pyridinyl group, or a cyano group.

2. The organic compound of claim 1 , wherein:

the organic compound is represented by Chemical Formula 1A,

the organic compound represented by Chemical Formula 1A is represented by one of Chemical Formulae 1Aa to 1Ad:

wherein, in Chemical Formulae 1Aa to 1Ad,

Z 1 to Z 3 are independently N or CH,

at least two of Z 1 to Z 3 are N,

Ar 1 and Ar 2 are independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted pyridinyl group,

L is a single bond or a substituted or unsubstituted phenylene group,

X 1 and X 2 are independently O or S,

R 1 to R 8 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted phenyl group, or a cyano group, and

‘substituted’ refers to replacement of at least one hydrogen of a substituent by deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group, a pyridinyl group, or a cyano group.

3. The organic compound of claim 1 , wherein:

the organic compound is represented by Chemical Formula 1B,

the organic compound represented by Chemical Formula 1B is represented by one of Chemical Formulae 1Ba to 1Bd:

wherein, in Chemical Formulae 1Ba to 1Bd,

Z 1 to Z 3 are independently N or CH,

at least two of Z 1 to Z 3 are N,

Ar 1 and Ar 2 are independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted pyridinyl group,

L is a single bond or a substituted or unsubstituted phenylene group,

X 1 and X 2 are independently O or S,

R 1 to R 8 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted phenyl group, or a cyano group, and

‘substituted’ refers to replacement of at least one hydrogen of a substituent by deuterium, a C1 to C5 alkyl group, a C6 to C18 aryl group, a pyridinyl group, or a cyano group.

4. The organic compound of claim 1 , wherein L is a single bond, a phenylene group, or a cyano-substituted phenylene group.

5. The organic compound of claim 1 , wherein X 1 and X 2 are each O.

6. The organic compound of claim 1 , wherein the organic compound is one of compounds listed in Group 1:

7. An organic optoelectronic device, comprising:

an anode and a cathode facing each other, and

an organic layer disposed between the anode and the cathode,

wherein the organic layer comprises the organic compound of claim 1 .

8. The organic optoelectronic device of claim 7 , wherein:

the organic layer comprises a light emitting layer, and

the organic compound is a host of the light emitting layer.

9. A display device comprising the organic optoelectronic device of claim 7 .

10. A composition comprising

a first organic compound, the first organic compound being the organic compound of claim 1 , and

a second organic compound comprising a carbazole moiety represented by Chemical Formula 2:

wherein, in Chemical Formula 2,

Y 1 is a single bond, a substituted or unsubstituted C6 to C30 arylene group, or a divalent substituted or unsubstituted C2 to C30 heterocyclic group,

A 1 is a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,

R 20 to R 25 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and

R 22 to R 25 are independently present or adjacent groups of R 22 to R 25 are linked to each other to form a ring.

11. The composition of claim 10 , wherein the second organic compound is represented by Chemical Formula 2A or a combination of Chemical Formulae 2B-1 and 2B-2:

wherein, in Chemical Formula 2A, Chemical Formula 2B-1, or Chemical Formula 2B-2, Y 1 to Y 3 are independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a divalent substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

A 1 to A 3 are independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

R 20 to R 22 and R 26 to R 31 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

m is an integer of O to 2,

two adjacent *'s in Chemical Formula 2B-1 are combined with two *'s in Chemical Formula 2B-2, and

the other two *'s of Chemical Formula 2B-1 are each CR c and CR d , wherein R c and R d are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.

12. The composition of claim 11 , wherein A 1 to A 3 of Chemical Formula 2A, Chemical Formula 2B-1, and Chemical Formula 2B-2 are 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, or a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, or a combination thereof.

13. The composition of claim 11 , wherein the second organic compound is represented by one of Chemical Formulae 2A-1 and 2B-a to 2B-e:

wherein, in Chemical Formulae 2A-1 and 2B-a to 2B-e,

Y 1 to Y 3 are independently a single bond, a substituted or unsubstituted C6 to C30 arylene group, a divalent substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

A 1 to A 3 are 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, or a substituted or unsubstituted triphenylene group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted fluorenyl group, or a combination thereof, and

R 20 to R 22 and R 26 to R 30 are independently hydrogen, deuterium, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof.

14. An organic optoelectronic device, comprising:

an anode and a cathode facing each other, and

an organic layer disposed between the anode and the cathode,

wherein the organic layer comprises the composition of claim 10 .

15. The organic optoelectronic device of claim 14 , wherein:

the organic layer comprises a light emitting layer, and

the composition is a host of the light emitting layer.

16. A display device comprising the organic optoelectronic device of claim 14 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 17, 2020
From: LEE, HANILL; KIM, BYUNGKU; PARK, YOUNGSUNG; SHIN, CHANG JU; RYU, DONGKYU; LEE, SEUNGJAE; JANG, KIPO; JUNG, SUNG-HYUN
To: SAMSUNG SDI CO., LTD.; SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 052963/0327 →
Priority Claims (1)
KR 10-2017-0181463 · Dec 27, 2017 · national
Continuity (1)
Related Publication 20200388765A1 · Dec 10, 2020