Organic light-emitting device

Patent metadata

Field	Value
Publication number	US-12359118-B2
Application number	US-201514856487-A
Country	US
Kind code	B2
Filing date	Sep 16, 2015
Priority date	Mar 3, 2015
Publication date	Jul 15, 2025
Grant date	Jul 15, 2025

Abstract

An organic light-emitting device includes a first electrode; a second electrode facing the first electrode; an emission layer between the first electrode and the second electrode; a hole transport region between the first electrode and the emission layer; and an electron transport region between the emission layer and the second electrode, wherein the emission layer includes a first material represented by Formula 1 and a second material represented by any one of Formulae 2-1 to 2-5, and the hole transport region includes a third material represented by Formula 3. The organic light-emitting device may have high efficiency and a long lifespan.

First claim

What is claimed is:

1. An organic light-emitting device comprising:
a first electrode;
a second electrode facing the first electrode;
an emission layer between the first electrode and the second electrode;
a hole transport region between the first electrode and the emission layer; and
an electron transport region between the emission layer and the second electrode,
wherein the emission layer comprises a first material represented by Formula 1 and a second material represented by any one of Formulae 2-1 to 2-5, and
the hole transport region comprises a third material represented by Formula 3:

wherein, in Formulae 2-1 and 2-3 to 2-5,
A 21 and A 22 are each independently selected from among a quinoline, an isoquinoline, 2,6-naphthyridine, 1,8-naphthyridine, 1,5-naphthyridine, 1,6-naphthyridine, 1,7-naphthyridine, 2,7-naphthyridine, a quinoxaline, a phthalazine, a quinazoline, and a cinnoline;
wherein, in Formula 2-2,
A 21 and A 22 are each independently selected from among 2,6-naphthyridine, 1,8-naphthyridine, 1,5-naphthyridine, 1,6-naphthyridine, 1,7-naphthyridine, 2,7-naphthyridine, a phthalazine, and a cinnoline;
wherein, in Formulae 1, 2-1 to 2-5, and 3,
A 11 to A 14 , and A 31 are each independently selected from a benzene, a naphthalene, a pyridine, a pyrimidine, a quinoline, an isoquinoline, 2,6-naphthyridine, 1,8-naphthyridine, 1,5-naphthyridine, 1,6-naphthyridine, 1,7-naphthyridine, 2,7-naphthyridine, a quinoxaline, a phthalazine, a quinazoline, and a cinnoline;
X 11 is selected from O, S, N[(L 12 ) a12 -Ar 12 ], C(R 15 )(R 16 ), Si(R 15 )(R 16 ), P[(L 12 ) a12 -Ar 12 ], B[(L 12 ) a12 -Ar 12 ], and P(═O)[(L 12 ) a12 -Ar 12 ];
X 21 is C(R 23 ) or N;
X 22 is C(R 24 ) or N;
Y 1 is N[(L 21 ) a21 -Ar 21 ];
Y 2 is selected from N[(L 22 ) a22 -Ar 22 ], O, S, and Si(R 25 )(R 26 );
X 31 is selected from O, S, and N[(L 31 ) a31 -Ar 31 ];
L 11 to L 13 , L 21 , L 22 , and L 31 to L 34 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, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group;
a11 to a13, a21, a22, and a31 to a34 are each independently selected from 0, 1, 2, and 3, and when all is 2 or greater, two or more L 11 s are identical to or different from each other, when a12 is 2 or greater, two or more L 12 s are identical to or different from each other, when a13 is 2 or greater, two or more L 13 s are identical to or different from each other, when a21 is 2 or greater, two or more L 21 s are identical to or different from each other, when a22 is 2 or greater, two or more L 22 s are identical to or different from each other, when a31 is 2 or greater, two or more L 31 s are identical to or different from each other, when a32 is 2 or greater, two or more L 32 s are identical to or different from each other, when a33 is 2 or greater, two or more L 33 s are identical to or different from each other, and when a34 is 2 or greater, two or more L 34 s are identical to or different from each other;
Ar 11 and Ar 12 are each independently HT 2 , and
Ar 21 and Ar 22 are each independently selected from:
a pyrrolyl 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 isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a thiadiazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group;
a pyrrolyl 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 isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a thiadiazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group, each substituted with at least one selected from 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 or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C 1 -C 10 alkyl group, a C 1 -C 10 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl 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, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, —Si(Q 31 )(Q 32 )(Q 33 ), —B(Q 34 )(Q 35 ), and —N(Q 36 )(Q 37 ); and
a pyrrolyl 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 isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a thiadiazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group, each substituted with at least one selected from a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anth

Assignees

• Samsung Display Co Ltd

Inventors

• Lee Jae-Yong
• Cho Hwan-Hee

Classifications

• H10K85/00 Primary

  Organic materials used in the body or electrodes of devices covered by this subclass · CPC title

• H10K2102/103

  comprising indium oxides, e.g. ITO · CPC title

• H10K2101/90

  Multiple hosts in the emissive layer · CPC title

• H10K2101/10

  Triplet emission · CPC title

• H10K85/6576

  comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene · CPC title