IP Library Granted Patent US 12,247,039
Granted Patent B2
US 12,247,039 · App. 17/104,051 · Granted Mar 11, 2025

Organometallic compound, organic light-emitting device including organometallic compound and electronic apparatus including the organic light-emitting device

Inventors: Minsik Min (Suwon-si, KR); Hyejin Bae (Suwon-si, KR); Soonok Jeon (Suwon-si, KR); Inkoo Kim (Suwon-si, KR); Jong Soo Kim (Hanam-si, KR); Sungho Nam (Daegu, KR); Hyeonho Choi (Seoul, KR)
Assignee: SAMSUNG ELECTRONICS CO., LTD.
C07F1/10C07F15/0066H10K85/346H10K85/371H10K85/631H10K50/15H10K50/16
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Quick Facts
Patent No.
US 12,247,039
App. No.
17/104,051
Granted
Mar 11, 2025
Kind
B2
Abstract

Provided are an organometallic compound represented by Formula 1, an organic light-emitting device including the organometallic compound and an electronic apparatus including the organic light-emitting device: Formula 1 may be understood by referring to the descriptions of Formula 1 provided herein.

Claims (83)

1. An organometallic compound represented by Formula 1:

wherein,

M in Formula 1 is Pt,

a bond between X 1 and M and a bond between X 4 and M in Formula 1 are each a coordinate bond and a bond between X 2 and M and a bond between X 3 and M in Formula 1 are each a covalent bond,

the group represented by

in Formula 1 is represented by one of Formulae CY1-26 to CY1-41 or one of Formulae CY1-Z46 to CY1-Z61,

wherein, in Formulae CY1-26 to CY1-1-41 and Formulae CY1-Z46 to CY1-Z61,

X 1 is C,

* indicates a binding site to M in Formula 1, and

*′ indicates a binding site to T 3 in Formula 1,

ring CY 2 is a benzene group represented by Formula CY2(1),

wherein, in Formula CY2(1),

X 2 is C,

*′ indicates a binding site to T 3 in Formula 1,

* indicates a binding site to M in Formula 1, and

* ″ indicates a binding site to T 1 in Formula 1,

ring CY 3 is a carbazole group represented by Formula CY3(1),

wherein, in Formula CY3(1),

X 3 is C,

X 31 is a single bond,

*″ indicates a binding site to T 1 in Formula 1,

* indicates a binding site to M in Formula 1, and

*′ indicates a binding site to T 2 in Formula 1,

ring CY 4 is a pyridine group represented by Formula CY4(1),

wherein, in Formula CY4(1),

X 4 is N,

* indicates a binding site to M in Formula 1, and

*′ indicates a binding site to T 2 in Formula 1,

n1 to n3 in Formula 1 are each 1,

T 1 in Formula 1 is *—S—*′ or *—O—*′,

T 2 in Formula 1 is a single bond,

T 3 in Formula 1 is a single bond,

n4 in Formula 1 is 0 and T 4 is not present,

R 11 in Formulae CY1-26 to CY1-41 is a phenyl group substituted with a C 1 -C 60 alkyl group, a deuterated C 1 -C 60 alkyl group, or any combination thereof,

R 12 to R 15 in Formulae CY1-26 to CY1-41 and CY1-Z46 to CY1-Z61, R 2 in Formula 1 and R 4 in Formula 1 are each independently hydrogen, deuterium, a C 1 -C 60 alkyl group, or a deuterated C 1 -C 60 alkyl group,

R 3 in Formula 1 is:

hydrogen, deuterium, a C 1 -C 60 alkyl group, or a deuterated C 1 -C 60 alkyl group, or

a phenyl group unsubstituted or substituted with deuterium, a C 1 -C 60 alkyl group, a deuterated C 1 -C 60 alkyl group, or any combination thereof,

a2 to a4 in Formula 1 are each independently an integer from 0 to 3,

Z 11 in Formulae CY1-Z46 to CY1-Z61 and Z 2 to Z 4 in Formula 1 are each independently a group represented by Formula 2:

one of Q 51 to Q 53 in Formula 2 is a benzene group unsubstituted or substituted with deuterium, a C 1 -C 60 alkyl group, a deuterated C 1 -C 60 alkyl group, or any combination thereof,

two of Q 51 to Q 53 in Formula 2 are each independently —CH 3 , —CD 3 , —CD 2 H, or —CDH 2 ,

L 1 in Formula 2 is a single bond or a benzene group,

c1 in Formula 2 is 1,

c2 in Formula 2 is 1 or 2,

* in Formula 2 indicates a binding site to an adjacent atom,

b2 to b4 in Formula 1 are each 0 or 1,

(a) or (b) is true:

(a) when the group represented by

in Formula 1 is represented by one of Formulae CY1-26 to CY1-41, then the sum of b2 to b4 in Formula 1 is 1, L 1 in Formula 2 is a single bond, and c2 in Formula 2 is 1,

(b) when the group represented by

in Formula 1 is represented by one of Formulae CY1-Z46 to CY1-Z61, then b2 to b4 in Formula 1 are each 0, L 1 in Formula 2 is a benzene group, and c2 in Formula 2 is 1 or 2.

2. The organometallic compound of claim 1 , wherein a group represented by *—C(Q 51 )(Q 52 )(Q 53 ) in Formula 2 is represented by one of Formulae 2-1 to 2-20:

wherein, in Formulae 2-1 to 2-20,

Q 51 and Q 52 are each independently —CH 3 , —CD 3 , —CD 2 H, or —CDH 2 ,

Q 61 to Q 65 are each independently deuterium, a C 1 -C 60 alkyl group, or a deuterated C 1 -C 60 alkyl group, and

* indicates a binding site to L 1 in Formula 2.

3. The organometallic compound of claim 1 , wherein

the (b) is true, and

Z 11 in Formulae CY1-Z46 to CY1-Z61 is represented by one of Formulae 2(1) to 2(10):

wherein, in Formulae 2(1) to 2(10),

T 11 to T 15 are each a group represented by *—C(Q 51 )(Q 52 )(Q 53 ) in Formula 2,

T 11 to T 15 are identical to or different from each other,

R 10a is a hydrogen, and

* indicates a binding site to a nitrogen in Formulae CY1-Z46 to CY1-Z61.

4. An organic light-emitting device comprising:

a first electrode;

a second electrode; and

an organic layer disposed between the first electrode and the second electrode and comprising an emission layer;

wherein the organic layer comprises at least one organometallic compound of claim 1 .

5. The organic light-emitting device of claim 4 , wherein

the first electrode is an anode,

the second electrode is a cathode, and

the organic layer further comprises a hole transport region disposed between the first electrode and the emission layer and an electron transport region disposed between the emission layer and the second electrode,

wherein the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof, and

the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

6. An electronic apparatus comprising the organic light-emitting device of claim 4 .

7. The organic light-emitting device of claim 4 , wherein the emission layer comprises the organometallic compound.

8. The organic light-emitting device of claim 7 , wherein the emission layer further comprises a host.

9. The organic light-emitting device of claim 7 , wherein a ratio of emission components emitted from the organometallic compound is 80 percent (%) or more of the total emission components emitted from the emission layer.

10. The organic light-emitting device of claim 9 , wherein blue light is emitted from the organometallic compound.

11. The organic light-emitting device of claim 7 , wherein the emission layer further comprises a fluorescent dopant different from the organometallic compound.

12. The organic light-emitting device of claim 11 , wherein the fluorescent dopant comprises an amino group-containing compound.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 25, 2020
From: MIN, MINSIK; BAE, HYEJIN; JEON, SOONOK; KIM, INKOO; KIM, JONG SOO; NAM, SUNGHO; CHOI, HYEONHO
To: SAMSUNG ELECTRONICS CO., LTD.
Reel/Frame 054465/0726 →
Priority Claims (2)
KR 10-2019-0154355 · Nov 27, 2019 · national
KR 10-2020-0159546 · Nov 25, 2020 · national
Continuity (1)
Related Publication 20210171548A1 · Jun 10, 2021
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