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

Patent metadata

Field	Value
Publication number	US-12247039-B2
Application number	US-202017104051-A
Country	US
Kind code	B2
Filing date	Nov 25, 2020
Priority date	Nov 27, 2019
Publication date	Mar 11, 2025
Grant date	Mar 11, 2025

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.

First claim

What is claimed is:

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. T

Assignees

• Samsung Electronics Co Ltd

Inventors

• Min Minsik
• Bae Hyejin
• Jeon Soonok
• Kim Inkoo
• Kim Jong Soo
• Nam Sungho
• Choi Hyeonho

Classifications

• H10K50/16

  Electron transporting layers · CPC title

• H10K50/15

  Hole transporting layers · CPC title

• H10K85/631

  Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine · CPC title

• H10K85/371

  Metal complexes comprising a group IB metal element, e.g. comprising copper, gold or silver · CPC title

• H10K85/346

  comprising platinum · CPC title