Condensed cyclic compound and an organic light-emitting device including the same

Patent metadata

Field	Value
Publication number	US-10553799-B2
Application number	US-201615395801-A
Country	US
Kind code	B2
Filing date	Dec 30, 2016
Priority date	Jun 20, 2016
Publication date	Feb 4, 2020
Grant date	Feb 4, 2020

Abstract

A condensed cyclic compound represented by Formula 1 and an organic light-emitting device including the same.

First claim

What is claimed is:

1. An organic light-emitting device, comprising:
a first electrode;
a second electrode facing the first electrode; and
an organic layer disposed between the first electrode and the second electrode, the organic layer comprising an emission layer,

wherein the organic layer comprises at least one of a condensed cyclic compound represented by Formula 1:

wherein A 1 and A 2 in Formula 1 are each independently selected from a benzene group, a naphthalene group, a quinoline group, an isoquinoline group, or a quinazoline group,
L 1 to L 3 in Formula 1 are each independently selected from a substituted or unsubstituted 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, a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group, *—P(═O)(Q 4 )-*′, *—P(═S)(Q 4 )-*′, *—S(═O)—*′, or *—S(═O) 2 —*′,
a1 to a3 in Formula 1 are each independently an integer selected from 0 to 7, wherein when a1 is 2 or greater, at least two L 1 (s) are the same or different from each other, when a2 is 2 or greater, at least two L 2 (s) are the same or different from each other, and when a3 is 2 or greater, at least two L 3 (s) are the same or different from each other,
Ar 1 and Ar 2 in Formula 1 are each independently selected from 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, —S(═O) 2 (Q 4 ), —P(═O)(Q 4 )(Q 5 ), —P(═S)(Q 4 )(Q 5 ), or —S(═O)(Q 4 ),
Ar 3 in Formula 1 is selected from groups represented by Formulae 3-1 to 3-31:

Y 31 is selected from O, S, C(Z 35 )(Z 36 ), N(Z 37 ), or Si(Z 38 )(Z 39 ),
Z 31 to Z 39 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 20 alkyl group, a C 1 -C 20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a spiro-benzofluorene-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, a benzothiazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a naphthobenzosilolyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, a dinaphthosilolyl group, a thiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an oxazolopyridinyl group, a thiazolopyridinyl group, a benzonaphthyridinyl group, an azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azadibenzosilolyl group, an indenopyrrolyl group, an indolopyrrolyl group, an indenocarbazolyl group, or an indolocarbazolyl group,
e2 is an integer selected from 0 or 2,
e3 is an integer selected from 0 to 3,
e4 is an integer selected from 0 to 4,
e5 is an integer selected from 0 to 5,
e6 is an integer selected from 0 to 6,
e7 is an integer selected from 0 to 7, and
e9 is an integer selected from 0 to 9;
b1 to b3 in Formula 1 are each independently an integer selected from 1 to 7, wherein when b1 is two or greater, at least two Ar 1 (s) are the same or different from each other, when b2 is two or greater, at least two Ar 2 (s) are the same or different from each other, and when b3 is two or greater, at least two Ar 3 (s) are the same or different from each other,
c1 and c2 in Formula 1 are each independently an integer selected from 0 to 6, and c3 is an integer selected from 1 to 2,
c1 to c3 satisfy the formula of c1+c2+c3≥1,
provided that, if c3 is 2, *-(L 3 ) a3 -(Ar 3 ) b3 is not a phenyl group or a substituted phenyl group,
R 11 and R 12 , in Formula 1 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 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 aryithio 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 ), or —S(═O) 2 (Q 1 ),
R 13 in Formula 1 is selected from:
hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino gr

Assignees

• Samsung Display Co Ltd

Inventors

• Park Junha
• Kim Youngkook
• Sim Munki
• Lee Hyoyoung
• Jeong Eunjae
• Hwang Seokhwan

Classifications

• C09K2211/1092

  containing sulfur as the only heteroatom · CPC title

• C07D405/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D241/38 Primary

  with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms · CPC title

• C09K2211/1044

  containing two nitrogen atoms as heteroatoms · CPC title

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title