IP Library › Granted Patent US 11,723,270
Granted Patent B2
US 11,723,270 · App. 16/629,671 · Granted Aug 8, 2023

Organic optoelectronic diode and display device

Inventors: Kipo Jang (Suwon-si, KR); Byungku Kim (Suwon-si, KR); Giwook Kang (Suwon-si, KR); Hanill Lee (Suwon-si, KR); Sung-Hyun Jung (Suwon-si, KR); Ho Kuk Jung (Suwon-si, KR); Youngkyoung Jo (Suwon-si, KR); Eun Sun Yu (Suwon-si, KR)
Assignee: SAMSUNG SDI CO., LTD.
H10K85/6572C07D405/14C07D487/04C07F15/0033C09K11/06H10K85/342H10K85/654H10K85/6574C09K2211/1029C09K2211/1033C09K2211/185H10K50/11H10K71/00H10K71/164H10K2101/10H10K2101/90H10K2102/351
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Quick Facts
Patent No.
US 11,723,270
App. No.
16/629,671
Granted
Aug 8, 2023
Kind
B2
Abstract

Disclosed are an organic optoelectronic device includes an anode and a cathode facing each other and an organic layer disposed between the anode and the cathode, wherein the organic layer includes at least one of a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, and the light emitting layer includes a first host, a second host, and a phosphorescent dopant represented by Chemical Formula 4, and a display device including the same.

Claims (52)

1. 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 includes at least one of a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer,

wherein the light emitting layer includes a first host represented by Chemical Formula 1-3a-II, Chemical Formula 1-3a-III, Chemical Formula 1-3a-IV, or Chemical Formula 1-3a-V, a second host represented by a combination of Chemical Formula 2 and Chemical Formula 3, and a phosphorescent dopant represented by Chemical Formula 4,

wherein, in Chemical Formula 1-3a-II, Chemical Formula 1-3a-III, Chemical Formula 1-3a-IV, and Chemical Formula 1-3a-V,

X 1 is O or S,

Z 1 to Z 3 are independently N or CR a ,

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

L 1 is a single bond, or a substituted or unsubstituted C6 to C20 arylene group,

R 1 is a substituted or unsubstituted C6 to C20 aryl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and

R a , R 2 to R 4 , and R 10 to R 13 are independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group;

wherein, in Chemical Formula 2 and Chemical Formula 3,

Y 1 and Y 2 are 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,

adjacent two *'s of Chemical Formula 2 are linked with Chemical Formula 3,

* of Chemical Formula 2 that are not linked with Chemical Formula 3 are independently C-L a -R b ,

L a , L 3 , and L 4 are independently a single bond, or a substituted or unsubstituted C6 to C20 arylene group,

R b and R 5 to R 8 are independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group;

wherein, in Chemical Formula 4,

Z 4 to Z 11 are independently N, C or CR c ,

the ring C is bound to the ring B through a C—C bond,

iridium is bound to the ring B through a Ir—C bond,

X 2 is O or S,

R c and R 14 to R 19 are independently hydrogen, deuterium, a halogen, germanium group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C10 alkylsilyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and

n is an integer ranging from 1 to 3.

2. The organic optoelectronic device of claim 1 , wherein Z 1 to Z 3 of Chemical Formula 1-3a-II, Chemical Formula 1-3a-III, Chemical Formula 1-3a-IV, and Chemical Formula 1-3a-V are N.

3. The organic optoelectronic device of claim 1 , wherein R 1 of Chemical Formula 1-3a-II, Chemical Formula 1-3a-III, Chemical Formula 1-3a-IV, and Chemical Formula 1-3a-V is selected from substituents of Group I:

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

4. The organic optoelectronic device of claim 1 , wherein the second host is represented by one of Chemical Formula 2A, Chemical Formula 2B, Chemical Formula 2C, and Chemical Formula 2D:

wherein, in Chemical Formula 2A to Chemical Formula 2D,

Y 1 and Y 2 are 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,

L a1 to L a4 , L 3 , and L 4 are independently a single bond, or a substituted or unsubstituted C6 to C20 arylene group, and

R b1 to R b4 and R 5 to R 8 are independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group.

5. The organic optoelectronic device of claim 4 , wherein R b1 to R b4 and R 5 to R 8 are independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted pyridinyl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.

6. The organic optoelectronic device of claim 1 , wherein Chemical Formula 4 is represented by one of Chemical Formula 4-1 to Chemical Formula 4-6:

wherein, in Chemical Formula 4-1 to Chemical Formula 4-6,

X 2 is O or S,

R c1 , R c2 , R c3 and R 14 to R 19 are independently hydrogen, deuterium, a halogen, germanium group, a cyano group, a substituted or unsubstituted silyl group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C3 to C20 cycloalkyl group, a substituted or unsubstituted C1 to C10 alkylsilyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, and

n is an integer ranging from 1 to 3.

7. The organic optoelectronic device of claim 1 , wherein:

the second host is represented by Chemical Formula 2B:

wherein, in Chemical Formula 2B,

L a1 , L a4 , L 3 , and L 4 are independently a single bond, or a substituted or unsubstituted C6 to C20 arylene group,

R b1 , R b4 , and R 5 to R 8 are independently hydrogen, deuterium, a cyano group, a substituted or unsubstituted C1 to C10 alkyl group, or a substituted or unsubstituted C6 to C20 aryl group, and

Y 1 and Y 2 are 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.

8. The organic optoelectronic device of claim 7 , wherein Chemical Formula 4 is represented by Chemical Formula 4-1:

wherein, in Chemical Formula 4-1,

X 2 is O or S,

R c1 , R c2 , R c3 , and R 14 to R 19 are independently hydrogen, deuterium, a halogen, a substituted or unsubstituted silyl group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkylsilyl group, or a substituted or unsubstituted C6 to C20 aryl group,

n is an integer ranging from 1 to 3,

“substituted” refers to replacement of at least one hydrogen of a substituent or a compound by deuterium, a halogen, a C1 to C4 alkyl group, or a C6 to C12 aryl group.

9. A display device comprising the organic optoelectronic device according to claim 1 .

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 9, 2020
From: JANG, KIPO; KIM, BYUNGKU; KANG, GIWOOK; LEE, HANILL; JUNG, SUNG-HYUN; JUNG, HO KUK; JO, YOUNGKYOUNG; YU, EUN SUN
To: SAMSUNG SDI CO., LTD.
Reel/Frame 051463/0155 →
Priority Claims (1)
KR 10-2017-0093029 · Jul 21, 2017 · national
Continuity (1)
Related Publication 20200161563A1 · May 21, 2020
Cited By (1)
US 12,256,630