Composition, thin film including the composition, and organic light-emitting device including the composition or the thin film

Patent metadata

Field	Value
Publication number	US-10243149-B2
Application number	US-201715399332-A
Country	US
Kind code	B2
Filing date	Jan 5, 2017
Priority date	Jan 5, 2016
Publication date	Mar 26, 2019
Grant date	Mar 26, 2019

Abstract

A composition including a first compound represented by Formula 1 and a second compound represented by Formula 2:

Ar 1 -(L 1 ) a1 -Ar 2   Formula 1

Ar 11 -(L 11 ) a11 -Ar 12   Formula 2

wherein Ar 1 , Ar 2 , Ar 11 , Ar 12 , L 1 , L 11 , a1, and a11 are the same as described in the specification.

First claim

What is claimed is:

1. A composition comprising:
a first compound represented by Formula 1; and
a second compound represented by Formula 2:
Ar 1 -(L 1 ) a1 -Ar 2   Formula 1

Ar 11 -(L 11 ) a11 -Ar 12   Formula 2

wherein
Ar 1 in Formula 1 is a group represented by Formula 11 or 12,
Ar 2 in Formula 1 is a group represented by Formula 13 or 14,
Y 1 in Formula 12 is O, S, or N(R 21 ),
Y 2 in Formula 14 is O, S, or N(R 22 ),
L 1 in Formula 1 is a group represented by Formula 15,
a1 in Formula 1 is an integer selected from 1 to 5, wherein when a1 is two or more, two or more groups L 1 are identical to or different from each other,
R 1 to R 5 , R 21 and R 22 in Formulae 11 to 15 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, 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 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 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -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 7 -C 60 arylalkyl group, a substituted or unsubstituted C 1 -C 60 heteroaryl group, a substituted or unsubstituted C 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted C 2 -C 60 heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and —Si(Q 1 )(Q 2 )(Q 3 ),
b1 to b5 in Formulae 11 to 15 are each independently an integer selected from 0 to 4,
the number of the cyano group comprised in a group represented by *-(L 1 ) a1 -*′ in Formula 1is denoted as “c5”, and the sum of c1 to c5 in Formula 1 is an integer selected from 1 to 5,
i) when Ar 1 in Formula 1 is a group represented by Formula 12, Ar 2 in Formula 1 is a group represented by Formula 14 , and Y 1 in Formula 12 is N(R 21 ), Y 2 in Formula 14 is O or S, and
ii) when Ar 1 in Formula 1 is a group represented by Formula 12, Ar 2 in Formula 1 is a group represented by Formula 14, and Y 2 in Formula 14 is N(R 22 ), Y 1 in Formula 12 is O or S,
Ar 11 in Formula 2 is a group represented by Formula 21 or 22,
Ar 12 in Formula 2 is selected from:
a group represented by Formula 23 or 24;
a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group not comprising a double bond between N and C, a C 6 -C 60 aryl group, a biphenyl group, a terphenyl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 arylalkyl group, a C 1 -C 60 heteroaryl group not comprising a double bond between N and C, a C 1 -C 60 heteroaryloxy group not comprising a double bond between N and C, a C 1 -C 60 heteroarylthio group not comprising a double bond between N and C, a C 2 -C 60 heteroarylalkyl group not comprising a double bond between N and C, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group not comprising a double bond between N and C; and
a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group not comprising a double bond between N and C, a C 6 -C 60 aryl group, a biphenyl group, a terphenyl group, a C 1 -C 60 heteroaryl group not comprising a double bond between N and C, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group not comprising a double bond between N and C, each substituted with at least one selected from deuterium, an amino group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a biphenyl group, a terphenyl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group not comprising a double bond between N and C, and —Si(Q 11 )(Q 12 )(Q 13 ),
A 1 and A 2 in Formulae 21 to 24 are each independently selected from:
a single bond, a C 1 -C 4 alkylene group, and a C 2 -C 4 alkenylene group; and
a C 1 -C 4 alkylene group and a C 2 -C 4 alkenylene group, each substituted with at least one selected from deuterium, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and —Si(Q 21 )(Q 22 )(Q 23 ),
Y 11 in Formula 22 is O, S, or N(R 41 ),
Y 12 in Formula 24 is O, S, or N(R 42 ),
R 11 to Ru in Formulae 21 to 24 and R 41 and R 42 are each independently selected from:
hydrogen, deuterium, an amino group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, and a 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, and a C 1 -C 60 alkoxy group, each substituted with at least one selected from deuterium and an amino group;
a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group not comprising a double bond between N and C, a C 6 -C 60 aryl group, a biphenyl group, a terphenyl group, a C 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 7 -C 60 arylalkyl group, a C 1 -C 60 heteroaryl group not comprising a double bond between N and C, a C 1 -C 60 heteroaryloxy group not comprising a double bond between N and C, a C 1 -C 60 heteroarylthio group not comprising a double bond between N and C, a C 2 -C 60 heteroarylalkyl group not comprising a double bond between N and C, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group not comprising a double bond between N and C;
a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group not comprising a double bond between N and C, a C 6 -C 60 aryl group, a biphenyl group, a terphenyl group, a C 1 -C 60 heteroaryl group not comprising a double bond between N and C, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group not comprising a double bond between N and C, each substituted with at least one selected from deuterium, an amino group, a C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a biphenyl group, a terphenyl group, a

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Kang Hosuk
• Kim Hyunjung
• Lee Namheon
• Chae Miyoung
• Kim Sangmo
• Kim Jongsoo
• Kim Joonghyuk
• Sim Myungsun
• Ihn Sooghang
• Jeon Soonok
• Chung Yeonsook
• Jung Yongsik
• Huh Dalho

Classifications

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title

• C09K11/06 Primary

  containing organic luminescent materials · CPC title

• C09K2211/1014

  bridged by heteroatoms, e.g. N, P, Si or B · CPC title

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title