Borole compound and organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-10259996-B2
Application number	US-201715584826-A
Country	US
Kind code	B2
Filing date	May 2, 2017
Priority date	Aug 23, 2016
Publication date	Apr 16, 2019
Grant date	Apr 16, 2019

Abstract

A borole compound is represented by Formula 1: X 11 —(R 11 ) b11 . X 11 , R 11 , and b11 are as defined herein. An organic light-emitting device includes the borole compound. The organic light-emitting device includes a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, the organic layer including an emission layer. The organic layer includes the borole compound.

First claim

What is claimed is:

1. A borole compound represented by Formula 1:
X 11 —(R 11 ) b11 ,  Formula 1

wherein, in Formula 1,
X 11 is selected from a substituted or unsubstituted triazine, a substituted or unsubstituted vinylene carbonate, a substituted or unsubstituted thiophene, a substituted or unsubstituted furan, a substituted or unsubstituted dibenzoborole, a substituted or unsubstituted azulene, a substituted or unsubstituted naphthalene, a substituted or unsubstituted anthracene, and a substituted or unsubstituted pyrene, and
R 11 is represented by one of Formulae 2-1 to 2-3:

wherein b11 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10, wherein, when b11 is two or more, a plurality of R 11 (s) are identical to or different from each other,
in Formulae 2-1 to 2-3,
L 21 is selected from a substituted or unsubstituted C 1 -C 10 alkylene group, a substituted or unsubstituted C 2 -C 10 alkenylene group, a C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenylene group, a substituted or unsubstituted C 6 -C 60 arylene group, a substituted or unsubstituted C 1 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,
a21 is 0 or 1,
R 21 to R 24 are each independently selected from R EW , hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, 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 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, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 ), and —P(═O)(Q 1 )(Q 2 ), provided that at least one of R 21 to R 24 is R EW ,
R EW is an electron withdrawing group,
Q 1 to Q 3 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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 C 1 -C 60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, and
* indicates a binding site to a neighboring atom.

2. The borole compound of claim 1 , wherein:
X 11 is represented by one of Formulae 3-1 to 3-9:

wherein, in Formulae 3-1 to 3-9,
R 31 to R 33 are each independently selected from:
a binding site to R 11 , hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 10 alkyl group, a C 2 -C 10 alkenyl group, a C 2 -C 10 alkynyl group, and a C 1 -C 10 alkoxy group;
a C 1 -C 10 alkyl group, a C 2 -C 10 alkenyl group, a C 2 -C 10 alkynyl group, and a C 1 -C 10 alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono 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 10 aryl group, a C 6 -C 10 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 10 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic 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 10 aryl group, a C 6 -C 10 aryloxy group, a C 6 -C 10 arylthio group, a C 1 -C 10 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group; 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, a C 6 -C 10 aryl group, a C 6 -C 10 aryloxy group, a C 6 -C 10 arylthio group, a C 1 -C 10 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 10 alkyl group, a C 2 -C 10 alkenyl group, a C 2 -C 10 alkynyl group, a C 1 -C 10 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 10 aryl group, a C 6 -C 10 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 10 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group,
at least one selected from R 31 , the number of which is the same as b11, is a binding site to R 11 , at least one selected from R 31 and R 32 , the number of which is the same as b11, is a binding site to R 11 , or at least one selected from R 31 to R 33 , the number of which is the same as b11, is a binding site to R 11 ,
b31 is selected from 1, 2, 3, and 4,
b32 is selected from 1, 2, and 3,
b33 is selected from 1, 2, 3, 4, and 5,
b34 is selected from 1, 2, 3, 4, 5, and 6, and
b35 is selected from 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10.

3. The borole compound of claim 1 , wherein:
X 11 is represented by one of Formulae 4-1 to 4-9:

wherein, in Formula 4-1 to 4-9,
* indicates a binding site to R 11 , and
R 41 to R 46 are each independently selected from:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, a methoxy group, an ethoxy group, an n-propoxy group, an iso-propoxy group, an n-butoxy group, a sec-butoxy group, an iso-butoxy group, and a tert-butoxy group;
a phenyl group and a naphthyl group; and
a phenyl group and a naphthyl group, each substituted with at least o

Assignees

• Samsung Display Co Ltd

Inventors

• Kang Sunwoo
• Jeon Sangho
• Cho Youngmi

Classifications

• C07D317/10

  not condensed with other rings · CPC title

• C07D333/10

  Thiophene · CPC title

• C07D251/14 Primary

  with hydrogen or carbon atoms directly attached to at least one ring carbon atom · CPC title

• C09K11/63 Primary

  containing boron · CPC title

• C07C2603/72

  Ethanonaphthalenes; Hydrogenated ethanonaphthalenes · CPC title