Organic light-emitting device

Patent metadata

Field	Value
Publication number	US-11871661-B2
Application number	US-201615377732-A
Country	US
Kind code	B2
Filing date	Dec 13, 2016
Priority date	Dec 17, 2015
Publication date	Jan 9, 2024
Grant date	Jan 9, 2024

Abstract

An organic light-emitting device includes: a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, the organic layer including an emission layer, wherein the organic layer includes a first compound represented by Formula 1 and a second compound represented by Formula 501. The organic light-emitting device including the first compound and the second compound may have low driving voltage, high efficiency, and high luminance.

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 between the first electrode and the second electrode, the organic layer comprising an emission layer,
wherein the organic layer comprises a first compound represented by one selected from Formulae 1-1 to 1-7, and a second compound represented by Formula 501:

wherein, in Formulae 1-1 to 1-7, 2A, 2B, and 501,
ring A 3 is a group represented by Formula 2A or a group represented by Formula 2B,
X 1 is N-[(L 11 ) a11 -(R 11 ) b11 ], O, or S,
X 2 is N-[(L 12 ) a12 -(R 12 ) b12 ], O, or S,
X 21 is N or C(R 21 ); X 22 is N or C(R 22 ); X 23 is N or C(R 23 ); X 24 is N or C(R 24 ); X 25 is N or C(R 25 ); X 26 is N or C(R 26 ); X 31 is N or C(R 31 ); X 32 is N or C(R 32 ); X 33 is N or C(R 33 ); X 34 is N or C(R 34 ); X 35 is N or C(R 35 ); and X 36 is N or C(R 36 ),
provided that at least one of X 31 to X 34 in Formula 1-1 is N, and when at least one of L 1 and L 2 in Formulae 1-5, 1-6 and 1-7 is a substituted or unsubstituted anthracenylene group, at least one of X 25 , X 26 and X 31 to X 34 in Formula 1-5 is N, at least one of X 21 , X 26 and X 31 to X 34 in Formula 1-6 is N, and at least one of X 21 , X 22 and X 31 to X 34 in Formula 1-7 is N,
Ar 501 is selected from a substituted or unsubstituted C 5 -C 30 carbocyclic group and a substituted or unsubstituted C 2 -C 30 heterocyclic group,
provided that Ar 501 is not a pyrene group, and
provided that when Ar 501 is at least one selected from a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthrene group, an anthracene group, a fluoranthene group, a chrysene group, a naphthacene group, and a coronene group, then at least two selected from among R 501 and R 502 are substituted with —F,
L 1 and L 2 are each independently a substituted or unsubstituted condensed polycyclic group having three or more carbocyclic groups condensed with each other,
a1 and a2 are each independently an integer selected from 1 to 5, wherein when a1 is two or more, two or more L 1 (s) are identical to or different from each other; and when a2 is two or more, two or more L 2 (s) are identical to or different from each other,
L 11 , L 12 and L 501 to L 503 are each independently selected from a substituted or unsubstituted C 3 -C 10 cycloalkylene group, a substituted or unsubstituted C 1 -C 60 heterocycloalkylene group, a substituted or unsubstituted C 3 -C 10 cycloalkenylene group, a substituted or unsubstituted C 1 -C 60 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,
a11, a12, and xd1 to xd3 are each independently an integer selected from 0 to 5, wherein when a11 is two or more, two or more L 11 (s) are identical to or different from each other; when a12 is two or more, two or more L 12 (s) are identical to or different from each other; when xd1 is two or more, two or more L 501 (s) are identical to or different from each other; when xd2 is two or more, two or more L 502 (s) are identical to or different from each other; and when xd3 is two or more, two or more L 503 (s) are identical to or different from each other,
R 1 and R 2 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, and a C 1 -C 20 alkoxy group;
a C 1 -C 20 alkyl group and a C 1 -C 20 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, and a hydrazono group;
a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-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 naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group a dibenzosilolyl group;
a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-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 naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl 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 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 pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-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 naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, and —Si(Q 31 )(Q 32 )(Q 33 ); and
—Si(Q 1 )(Q 2 )(Q 3 ),
wherein Q 1 to Q 3 and Q 31 to Q 33 are each independently selected from a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, and a naphthyl group,
R 5 , R 6 , R 11 to R 13 , R 21 to R 26 , R 31 to R 36 , R 501 , and R 502 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

Assignees

• Samsung Display Co Ltd

Inventors

• Kim Sung-Wook
• Kim Myeong-Suk
• Cho Hwan-Hee
• Hwang Jin-Soo

Classifications

• H10K85/657 Primary

  Polycyclic condensed heteroaromatic hydrocarbons · CPC title

• C07D491/107 Primary

  with only one oxygen atom as ring hetero atom in the oxygen-containing ring · CPC title

• C07D495/10

  Spiro-condensed systems · CPC title

• C09K11/025

  non-luminescent particle coatings or suspension media · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title