Condensed cyclic compound, composition including the same, and organic light-emitting device including thin film formed from the composition

Patent metadata

Field	Value
Publication number	US-11453628-B2
Application number	US-201916518917-A
Country	US
Kind code	B2
Filing date	Jul 22, 2019
Priority date	Dec 5, 2018
Publication date	Sep 27, 2022
Grant date	Sep 27, 2022

Abstract

Provided are a condensed cyclic compound, a composition including the same, and an organic light-emitting device including a thin film formed from the composition. The condensed cyclic compound is represented by following Formula, has a molecular weight of about 400 to about 10,000, and comprises at least one cross-linkable group:

First claim

What is claimed is:

1. A condensed cyclic compound represented by Formula 1, wherein
the condensed cyclic compound has a molecular weight of about 400 to about 10,000, and
the condensed cyclic compound comprises at least one cross-linkable group:

wherein, in Formulae 1 to 3,
each of A 11 to A 13 is independently a group represented by Formula 2 or a group represented by Formula 3,
each of L 11 and L 12 is independently selected from a single bond, O, S, a C 5 -C 60 carbocyclic group, and a C 1 -C 60 heterocyclic group,
each of a11 and a12 is independently an integer from 0 to 5,
m11 is an integer from 0 to 15,
n11 is selected from 0 and 1, wherein, when n11 is 0,

is hydrogen,
each of R 21 to R 30 is independently selected from a cross-linkable group, 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 C 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio 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 ), —B(Q 1 )(Q 2 ), —N(Q 1 )(Q 2 ), —P(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(═O)(Q 1 )(Q 2 ), and —P(═S)(Q 1 )(Q 2 ),
each of A 31 and A 32 is independently selected from a cross-linkable group, a C 5 -C 60 carbocyclic group, and a C 1 -C 60 heterocyclic group,
each of L 31 to L 33 is independently selected from a substituted or unsubstituted C 5 -C 60 carbocyclic group and a substituted or unsubstituted C 1 -C 60 heterocyclic group,
each of a31 to a33 is independently an integer from 0 to 3,
each of b31 and b32 is independently an integer from 1 to 10,
each of R 31 to R 33 is 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 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 C 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio 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 ), —B(Q 1 )(Q 2 ), —N(Q 1 )(Q 2 ), —P(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(═O)(Q 1 )(Q 2 ), and —P(═S)(Q 1 )(Q 2 ),
each of Q 1 to Q 3 is 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 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group,
when each of A 11 to A 13 is a group represented by Formula 2, each cross-linkable group among R 21 to R 30 in Formula 2 is selected from groups represented by Formulae 8-1 to 8-5, and
when each of A 11 to A 13 is independently a group represented by Formula 3, each cross-linkable group among A 31 and A 32 in Formula 3 is selected from groups represented by Formulae 9-1 to 9-3:

wherein, in Formulae 8-1 to 8-5 and 9-1 to 9-3,
each of A 81 and A 91 is independently selected from a C 5 -C 60 carbocyclic group and a C 1 -C 60 heterocyclic group,
L 81 is selected from a substituted or unsubstituted C 5 -C 60 carbocyclic group and a substituted or unsubstituted C 1 -C 60 heterocyclic group,
a81 is an integer from 0 to 3,
each of R 81 to R 83 is 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 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 C 1 -C 60 heteroaryloxy group, a substituted or unsubstituted C 1 -C 60 heteroarylthio 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 ), —B(Q 1 )(Q 2 ), —N(Q 1 )(Q 2 ), —P(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O)(Q 1 ), —S(═O) 2 (Q 1 ), —P(═O)(Q 1 )(Q 2 ), and —P(═S)(Q 1 )(Q 2 ),
b81 is an integer from 1 to 3,
b82 is 1,
b83 is an integer from 1 to 2,
each of Q 1 to Q 3 is 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 6 -C 60 aryloxy group, a C 6 -C 60 arylthio group, a C 1 -C 60 heteroaryl group, a C 1 -C 60 heteroaryloxy group, a C 1 -C 60 heteroarylthio group, a monovalent non-a

Assignees

• Samsung Display Co Ltd

Inventors

• Kim Sehun
• Kim Eungdo
• NAM Eunju
• Noh Seunguk
• Park Jongwon
• Lee Hyunwoo
• Ha Jaekook

Classifications

• C07D333/78

  condensed with rings other than six-membered or with ring systems containing such rings · CPC title

• C07D209/80

  [b, c]- or [b, d]-condensed · CPC title

• C07D491/048

  the oxygen-containing ring being five-membered · CPC title

• C07D333/76

  Dibenzothiophenes · CPC title

• C07C2603/24

  Anthracenes; Hydrogenated anthracenes · CPC title