Composition and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-11760769-B2
Application number	US-201916669765-A
Country	US
Kind code	B2
Filing date	Oct 31, 2019
Priority date	Mar 29, 2019
Publication date	Sep 19, 2023
Grant date	Sep 19, 2023

Abstract

A composition including a first compound including a compound represented by Formula 1, a second compound including a compound represented by Formula 2, and a third compound including a compound represented by Formula 3, and an organic light-emitting device including the composition:

wherein the description of Formulae 1 to 3 are the same as described in the specification.

First claim

What is claimed is:

1. A composition comprising:
a first compound, a second compound, and a third compound, wherein the first compound comprises a compound represented by Formula 1, the second compound comprises a compound represented by Formula 2, and the third compound comprises a compound represented by Formula 3:

wherein
Y 2 in Formula 1 is C,
a group represented by

in Formula 1 is a group represented by Formula A(1):

wherein, in Formula A(1), R 9 and R 11 are each independently a C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, or a phenyl group, each unsubstituted or substituted with deuterium, a C 1 -C 20 alkyl group, a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a phenyl group, or any combination thereof, and R 10 and R 12 are each independently hydrogen or deuterium, *′indicates a binding site to Ir in Formula 1 , and *″ indicates a binding site to a neighboring atom in Formula 1 ,
Ar 1 , Ar 2 , and Ar n in Formulae 2 and 3 are each independently a C 5 -C 60 carbocyclic group which is unsubstituted or substituted with at least one R 61 or a C 1 -C 60 heterocyclic group which is unsubstituted or substituted with at least one R 61 ,
Ar 5 and A 12 in Formulae 2 and 3 are each independently a single bond, a C 5 -C 60 carbocyclic group which is unsubstituted or substituted with at least one R 65 , or a C 1 -C 60 heterocyclic group which is unsubstituted or substituted with at least one R 65 , or does not exist,
n in Formula 2 is 1, 2, or 3, and when n is 1, Ar 5 does not exist,
p in Formula 3 is 1, 2, or 3, and when p is 1, Ar 12 does not exist,
a1 and a2 in Formula 2 are each independently an integer from 0 to 5, and the sum of a1 and a2 is 1 or more,
ring CY 2 and ring CY 3 in Formula 2 are each independently a C 5 -C 60 carbocyclic group or a C 1 -C 60 heterocyclic group, and ring CY 2 and ring CY 3 are optionally linked to each other with a C 5 -C 60 carbocyclic group which is unsubstituted or substituted with at least one R 66 or a C 1 -C 60 heterocyclic group which is unsubstituted or substituted with at least one R 66 therebetween,
Het1 in Formula 3 is a π electron-depleted nitrogen-containing C 1 -C 60 cyclic group,
a11 and m in Formula 3 are each independently an integer from 1 to 10, R 1 to R 8 , A 1 to A 7 , R 20 , R 30 , R 61 , R 65 , R 66 , R 70 , and R 80 in Formulae 1 to 3 are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF 5 , a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazino group, a hydrazono group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a substituted or unsubstituted C 1 -C 60 alkyl group, a substituted or unsubstituted C 2 -C 60 alkenyl group, a substituted or unsubstituted C 2 -C 60 alkynyl group, a substituted or unsubstituted C 1 -C 60 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 60 aryl group, a substituted or unsubstituted C 6 -C 60 aryloxy group, a substituted or unsubstituted C 6 -C 60 arylthio group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Qs), —Ge(Q 3 )(Q 4 )(Qs), —B(Q 6 )(Q 7 ), —P(═O)(Qs)(Q 9 ), or —P(Qs)(Q 9 ), provided that at least one of R 1 to Rs is a fluoro group (—F),
b2, b3, b7, and b8 in Formulae 2 and 3 are each independently an integer from 0 to 20, when b2 is 2 or more, two or more R 20 (s) are identical to or different from each other, when b3 is 2 or more, two or more R 30 (s) are identical to or different from each other, when b7 is 2 or more, two or more R 70 (s) are identical to or different from each other, and when b8 is 2 or more, two or more R 80 (s) are identical to or different from each other,
two or more of R 1 to Rs in Formula 1 are optionally linked to form a C 5 -C 60 carbocyclic group which is unsubstituted or substituted with at least one Ria or a C 1 -C 0 heterocyclic group which is unsubstituted or substituted with at least one R 1 a,
two or more of A 1 to A 7 in Formula 1 are optionally linked to form a C 5 -C 60 carbocyclic group which is unsubstituted or substituted with at least one Ria or a C 1 -C 0 heterocyclic group which is unsubstituted or substituted with at least one R 1 a,
two or more of ring CY 2 , ring CY 3 , R 20 , and R 30 in Formula 2 are optionally linked to form a C 5 -C 60 carbocyclic group which is unsubstituted or substituted with at least one Ria or a C 1 -C 60 heterocyclic group which is unsubstituted or substituted with at least one R 1a ,
R 1a is understood by referring to the description of A 7 provided above, and
a substituent of the substituted C 1 -C 60 alkyl group, the substituted C 2 -C 60 alkenyl group, the substituted C 2 -C 60 alkynyl group, the substituted C 1 -C 60 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 2 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 2 -C 10 heterocycloalkenyl group, the substituted C 6 -C 60 aryl group, the substituted C 6 -C 60 aryloxy group, the substituted C 6 -C 60 arylthio group, the substituted C 1 -C 60 heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is:
deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or C 1 -C 60 alkoxy group;
a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, or a C 1 -C 60 alkoxy group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD 3 , —CD 2 H, —CDH 2 , —CF 3 , —CF 2 H, —CFH 2 , a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q 11 )(Q 12 ), —Si(Q 13 )(Q 14 )(Q 15 ), —Ge(Q 13 )(Q 14 )(Q 15 ), —B(Q 16 )(Q 17 ), —P(═O)(Q 18 )(Q 19 ), —P(Q 18 )(Q 19 ), or any combination thereof;
a C 3 -C 10 cycloalkyl group, a C 2 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 2 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 hete

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Lee Banglin
• Kang Dongmin
• Kim Soyeon
• Lee Jiyoun
• Cho Yongsuk
• Choi Jongwon
• Kravchuk Dmitry
• Kim Dongyeong
• Kim Junseok
• Lee Namheon
• Lee Byeonggwan
• Lee Sangshin
• Koishikawa Yasushi

Classifications

• H10K85/342 Primary

  comprising iridium · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C07F15/0033 Primary

  Iridium compounds · CPC title

• H10K85/615

  Polycyclic condensed aromatic hydrocarbons, e.g. anthracene · CPC title

• H10K85/622

  containing four rings, e.g. pyrene · CPC title