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

Patent metadata

Field	Value
Publication number	US-2024182505-A1
Application number	US-202318495925-A
Country	US
Kind code	A1
Filing date	Oct 27, 2023
Priority date	Oct 28, 2022
Publication date	Jun 6, 2024
Grant date	—

Abstract

An organometallic compound represented by Formula 1-1 or 1-2:

wherein, in Formulae 1-1 and 1-2, M is Pt or Pd; each of X 1 , X 2 , and X 3 is carbon; X 4 is nitrogen; T 8 is O, S, N(R 81 ), C(R 81 )(R 82 ), or Si(R 81 )(R 82 ); and the remaining substituent groups are as defined herein.

First claim

What is claimed is:

1 . An organometallic compound represented by Formula 1-1 or 1-2:

wherein, in Formulae 1-1 and 1-2,
M is Pt or Pd,
each of X 1 , X 2 , and X 3 is carbon,
X 4 is nitrogen,
X 11 is N, C(R 11 ), or C(R 0 ); X 12 is N, C(R 12 ), or C(R 0 ); X 13 is N, C(R 13 ), or C(R 0 ); and X 14 is N, C(R 14 ), or C(R 0 ),
X 21 is N, C(R 21 ), or C(R 0 ); X 22 is N, C(R 22 ), or C(R 0 ); and X 23 is N, C(R 23 ), or C(R 0 ),
X 31 is N, C(R 31 ), or C(R 0 ); X 32 is N, C(R 32 ), or C(R 0 ); X 33 is N, C(R 33 ), or C(R 0 ); X 34 is N, C(R 34 ), or C(R 0 ); X 35 is N, C(R 35 ), or C(R 0 ); and X 36 is N, C(R 36 ), or C(R 0 ),
X 41 is N, C(R 41 ), or C(R 0 ); X 42 is N, C(R 42 ), or C(R 0 ); X 43 is N, C(R 43 ), or C(R 0 ); and X 44 is N, C(R 44 ), or C(R 0 ),
T 8 is O, S, N(R 81 ), C(R 81 )(R 82 ), or Si(R 81 )(R 82 ),
each R 0 is independently a group represented by Formula 2,
R 11 to R 14 , R 21 to R 23 , R 31 to R 36 , R 41 to R 44 , R 51 to R 55 , R 61 to R 65 , R 71 to R 73 , R 81 , and R 82 are each independently:
a group represented by Formula 2;
hydrogen or deuterium; or
a C 1 -C 20 alkyl group, a phenyl group, or a carbazolyl group, each unsubstituted or substituted with at least one of deuterium, a C 1 -C 20 alkyl group, a phenyl group, a carbazolyl group, or a combination thereof,
wherein Condition A or Condition B is satisfied:
Condition A
each of X 21 to X 23 in Formulae 1-1 and 1-2 is not N, and A-i), A-ii) or A-iii) is true:
A-i) at least one of X 11 to X 14 in Formula 1-1 or at least one of X 11 and X 12 in Formula 1-2, at least one of X 31 to X 36 in Formulae 1-1 and 1-2, at least one of X 41 to X 44 in Formulae 1-1 and 1-2, or a combination thereof, is C(R 0 ),
A-ii) at least one of R 51 to R 55 in Formulae 1-1 and 1-2, at least one of R 61 to R 65 in Formulae 1-1 and 1-2, at least one of R 71 to R 73 in Formulae 1-1 and 1-2, at least one of R 81 and R 82 in Formulae 1-1 and 1-2, or a combination thereof, is a group represented by Formula 2, or
A-iii) at least one of X 11 to X 14 in Formula 1-1 or at least one of X 11 and X 12 in Formula 1-2, at least one of X 31 to X 36 in Formulae 1-1 and 1-2, at least one of X 41 to X 44 in Formulae 1-1 and 1-2, or a combination thereof, is C(R 0 ), and at least one of R 51 to R 55 in Formulae 1-1 and 1-2, at least one of R 61 to R 65 in Formulae 1-1 and 1-2, at least one of R 71 to R 73 in Formulae 1-1 and 1-2, at least one of R 81 and R 82 in Formulae 1-1 and 1-2, or a combination thereof, is a group represented by Formula 2,
Condition B
at least one of X 21 to X 23 in Formulae 1-1 and 1-2 is N, and B-i), B-ii) or B-iii) is true:
B-i) at least one of X 11 to X 14 in Formula 1-1 or at least one of X 11 and X 12 in Formula 1-2, at least one of X 21 to X 23 in Formulae 1-1 and 1-2, at least one of X 31 to X 36 in Formulae 1-1 and 1-2, at least one of X 41 to X 44 in Formulae 1-1 and 1-2, or a combination thereof, is C(R 0 ),
B-ii) at least one of R 51 to R 55 in Formulae 1-1 and 1-2, at least one of R 61 to R 65 in Formulae 1-1 and 1-2, at least one of R 71 to R 73 in Formulae 1-1 and 1-2, at least one of R 81 and R 82 in Formulae 1-1 and 1-2, or a combination thereof, is a group represented by Formula 2, or
B-iii) at least one of X 11 to X 14 in Formula 1-1 or at least one of X 11 and X 12 in Formula 1-2, at least one of X 21 to X 23 in Formulae 1-1 and 1-2, at least one of X 31 to X 36 in Formulae 1-1 and 1-2, at least one of X 41 to X 44 in Formulae 1-1 and 1-2, or a combination thereof, is C(R 0 ), and at least one of R 51 to R 55 in Formulae 1-1 and 1-2, at least one of R 61 to R 65 in Formulae 1-1 and 1-2, at least one of R 71 to R 73 in Formulae 1-1 and 1-2, at least one of R 81 and R 82 in Formulae 1-1 and 1-2, or a combination thereof, is a group represented by Formula 2, and
when the organometallic compound represented by Formulae 1-1 or 1-2 comprises at least two groups represented by Formula 2, the at least two groups represented by Formula 2 are identical to or different from each other,

wherein, in Formula 2,
Z 1 is:
hydrogen or deuterium; or
a C 1 -C 20 alkyl group, a phenyl group, or a carbazolyl group, each unsubstituted or substituted with at least one of deuterium, a C 1 -C 20 alkyl group, a phenyl group, a carbazolyl group, or a combination thereof,
Z 2 is hydrogen or deuterium,
Z 3 is a C 1 -C 20 alkyl group, a phenyl group, or a carbazolyl group, each unsubstituted or substituted with at least one of deuterium, a C 1 -C 20 alkyl group, a phenyl group, a carbazolyl group, or a combination thereof,
at least two of Z 1 to Z 3 are not linked to each other to form a ring, and
* indicates a binding site to a neighboring atom.

2 . The organometallic compound of claim 1 , wherein T 8 in Formulae 1-1 and 1-2 is O or S.

3 . The organometallic compound of claim 1 , wherein at least one of Conditions 1 to 8 is satisfied:
Condition 1 at least one of X 11 to X 14 in Formula 1-1 is C(R 0 ), or at least one of X 11 and X 12 in Formula 1-2 is C(R 0 ), Condition 2 at least one of X 31 and X 32 in Formulae 1-1 and 1-2 is C(R 0 ), Condition 3 at least one of X 33 to X 36 in Formulae 1-1 and 1-2 is C(R 0 ), Condition 4 at least one of X 41 to X 44 in Formulae 1-1 and 1-2 is C(R 0 ), Condition 5 at least one of R 51 to R 55 in Formulae 1-1 and 1-2 is a group represented by Formula 2, Condition 6 at least one of R 61 to R 65 in Formulae 1-1 and 1-2 is a group represented by Formula 2, Condition 7 at least one of R 71 to R 73 in Formulae 1-1 and 1-2 is a group represented by Formula 2, Condition 8 at least one of X 21 to X 23 in Formulae 1-1 and 1-2 is N, and at least one among the others of X 21 to X 23 is C(R 0 ).

4 . The organometallic compound of claim 3 , wherein at least one of Conditions 1 to 4 is satisfied.

5 . The organometallic compound of claim 3 , wherein at least one of Conditions 5 to 7 is satisfied.

6 . The organometallic compound of claim 1 , wherein the group represented by Formula 2 is a group represented by Formula 2(1) or a group represented by Formula 2(2):

wherein, in Formulae 2(1) and 2(2),
Z 1 and Z 2 are as defined in claim 1 ,
Z 11 to Z 13 and Z 31 to Z 33 are each independently:
hydrogen or deuterium;
a C 1 -C 15 alkyl group that is unsubstituted or substituted with at least one deuterium; or
a phenyl group that is unsubstituted or substituted with at least one of deuterium, a C 1 -C 10 alkyl group, or a combination thereof, and
* indicates a binding site to a neighboring atom.

7 . The organometallic compound of claim 6 , wherein Z 11 to Z 13 and Z 31 to Z 33 in Formulae 2(1) and 2(2) are each independently:
hydrogen or deuterium; a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-de

Assignees

• Samsung Electronics Co Ltd

Inventors

• Min Minsik
• Kim Hwang Suk
• Bae Hyejin
• Choi Hyesung
• Kang Hosuk
• Kim Jong Soo
• Kim Joonghyuk
• Son Youngmok
• Won Joonghee
• Jeong Daun
• Jung Yongsik
• Chwae Jun

Classifications

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K50/11

  characterised by the electroluminescent [EL] layers · CPC title

• H10K85/346

  comprising platinum · CPC title

• C07F15/0086 Primary

  Platinum compounds · CPC title