Organic light-emitting device

Patent metadata

Field	Value
Publication number	US-12232416-B2
Application number	US-201615293174-A
Country	US
Kind code	B2
Filing date	Oct 13, 2016
Priority date	May 10, 2016
Publication date	Feb 18, 2025
Grant date	Feb 18, 2025

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, a second compound, a third compound, and a fourth compound, and the first compound to the fourth compound satisfy Equations 1 to 8:E1,LUMO≥E2,LUMO+0.15 electron volts (eV)  Equation 1E1,HOMO≥E2,HOMO+0.15 eV  Equation 2E1,T1≥E4,T1  Equation 3E2,T1≥E4,T1  Equation 4E3,T1≥E4,T1  Equation 5E3,LUMO≥E2,LUMO+0.1 eV  Equation 6−5.6 eV≥E3,HOMO  Equation 7Egap1≥Egap3.  Equation 8

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 of Formulae 1-1, 2-1, 2-2, and 3-1, a second compound represented by one of Formulae 1-2, 2-3, 2-4, and 3-2, a third compound represented by Formula 4, and a fourth compound,
wherein when the first compound is represented by Formula 1-1, the second compound is represented by one of Formulae 2-3, 2-4, and 3-2, when the first compound is represented by Formulae 2-1 or 2-2, the second compound is represented by one of Formulae 1-2 and 3-2, and when the first compound is represented by Formula 3-1, the second compound is represented by one of Formulae 1-2, 2-3, and 2-4, and
wherein the first compound to the fourth compound satisfy Equations 1 to 8:
E 1,LUMO ≥E 2,LUMO +0.15 electron volts (eV)  Equation 1

E 1,HOMO ≥E 2,HOMO +0.15 eV  Equation 2

E 1,T1 ≥E 4,T1   Equation 3

E 2,T1 ≥E 4,T1   Equation 4

E 3,T1 ≥E 4,T1   Equation 5

E 3,LUMO ≥E 2,LUMO +0.1 eV  Equation 6

−5.6 eV≥ E 3,HOMO   Equation 7

E gap1 ≥E gap3 ,  Equation 8

wherein, in Equations 1 to 8,
E 1,LUMO indicates a lowest unoccupied molecular orbital (LUMO) energy level of the first compound,
E 2,LUMO indicates a LUMO energy level of the second compound, E 3,LUMO indicates a LUMO energy level of the third compound,
E 1,HOMO indicates a highest occupied molecular orbital (HOMO) energy level of the first compound,
E 2,HOMO indicates a HOMO energy level of the second compound,
E 3,HOMO indicates a HOMO energy level of the third compound,
E 1,T1 indicates a lowest excited triplet energy level of the first compound,
E 2,T1 indicates a lowest excited triplet energy level of the second compound,
E 3,T1 indicates a lowest excited triplet energy level of the third compound,
E 4,T1 indicates a lowest excited triplet energy level of the fourth compound,
E gap1 indicates a gap between the LUMO energy level of the first compound and the HOMO energy level of the first compound, and
E gap3 indicates a gap between the LUMO energy level of the third compound and the HOMO energy level of the third compound,

wherein, in Formulae 1-1, 1-2, 2-1 to 2-4, 3-1, 3-2, 4, and 5,
A 11 to A 14 , A 21 to A 23 , and A 51 are each independently selected from a C 5 -C 20 carbocyclic group and a C 1 -C 20 heterocyclic group,
X 11 is selected from O, S, N[(L 12 ) a12 -R 12 ], C[(L 12 ) a12 -R 12 ](R 17 ), Si[(L 12 ) a12 -R 12 ](R 17 ), P[(L 12 ) a12 -R 12 ], B[(L 12 ) a12 -R 12 ], and P(═O)[(L 12 ) a12 -R 12 ],
X 12 is selected from O, S, N[(L 15 ) a15 -R 19 ], C[(L 15 ) a15 -R 19 ](R 20 ), Si[(L 15 ) a15 -R 19 ](R 20 ), P[(L 15 ) a15 -R 19 ], B[(L 15 ) a15 -R 19 ], and P(═O)[(L 15 ) a15 -R 19 ],
X 21 is selected from N[(L 21 ) a21 -R 21 ], C[(L 21 ) a21 -R 21 ](R 23 ), O, and S,
X 22 is selected from N[(L 22 ) a22 -R 22 ], C[(L 22 ) a22 -R 22 ](R 24 ), O, and S,
X 51 is selected from N and CR 51 ,
X 71 is selected from N[(L 71 ) a71 -R 71 ], C[(L 71 ) a71 -R 71 ](R 73 ), O, and S,
X 72 is selected from N[(L 72 ) a72 -R 72 ], C[(L 72 ) a72 -R 72 ](R 74 ), O, and S,
R 12 and R 17 are optionally bound to form a saturated or unsaturated ring,
R 19 and R 20 are optionally bound to form a saturated or unsaturated ring,
L 11 to L 15 , L 21 , L 22 , L 41 to L 43 , L 61 to L 63 , L 71 , and L 72 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, provided that L 61 to L 63 are not each independently a carbazolylene group,
L 31 to L 33 are each independently selected from the group consisting of:
a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, a thiophenylene group, a furanylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a dibenzosilolylene group, a benzocarbazolylene group, and a dibenzocarbazolylene group; and
a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, a thiophenylene group, a furanylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a dibenzosilolylene group, a benzocarbazolylene group, and a dibenzocarbazolylene group, each substituted with at least one selected from deuterium, 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, a tert-butoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a thiophenyl group, a furanyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, —N(Q 31 )(Q 32 ), —Si(Q 31 )(Q 32 )(Q 33 ), and —B(Q 31 )(Q 32 ),
wherein Q 31 to Q 33 are each independently selected from 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 phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group,
a11 to a15, a21, a22, a31 to a33, a41 to a43, a61 to a63, a71, and a72 are each independently selected from 0, 1, 2, 3, 4, and 5,
at least one selected from L 41 to L 43 is a group represented by Formula 5,
wherein when L 41 is a group represented by Formula 5, a41 is selected from 1, 2, 3, 4, and 5; when L 42 is a group represented by Formula 5, a42 is selected from 1, 2, 3, 4, and 5; and when L 43 is a group represented by Formula 5, a43 is selected from 1, 2, 3, 4, and 5,
R 11 to R 27 , R 41 to R 43 , R 51 , R 52 , R 61 to R 66 , and R 71 to R 77 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 heterocycloalky

Assignees

• Samsung Display Co Ltd

Inventors

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

Classifications

• C09K2211/185

  of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C09K2211/1007

  Non-condensed systems · CPC title

• C09K11/06

  containing organic luminescent materials · CPC title

• C09K11/025 Primary

  non-luminescent particle coatings or suspension media · CPC title