Organic light-emitting device

Patent metadata

Field	Value
Publication number	US-11114625-B2
Application number	US-201514807778-A
Country	US
Kind code	B2
Filing date	Jul 23, 2015
Priority date	Dec 31, 2014
Publication date	Sep 7, 2021
Grant date	Sep 7, 2021

Abstract

An organic light-emitting device includes a first electrode; a second electrode; an organic layer between the first electrode and the second electrode, the organic layer including an emission layer, and an electron transport region between the emission layer and the second electrode. The emission layer includes a first compound represented by Formula 1 and a second compound represented by any one of Formulae 2-1 to 2-5. The electron transport region includes a third compound represented by Formula 7. The organic light-emitting device may have low driving voltage, 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; an organic layer between the first electrode and the second electrode, the organic layer comprising an emission layer, and
an electron transport region between the emission layer and the second electrode,
wherein the emission layer comprises a first compound represented by Formula 1 and a second compound represented by any one of Formulae 2-1 to 2-5; and
wherein the electron transport region comprises a third compound represented by Formula 7:

wherein in Formulae 1, 2-1 to 2-5, and 7,
A 11 , A 12 , A 13 , A 14 , A 21 , and A 22 are each independently selected from a benzene, a naphthalene, a pyridine, a pyrimidine, a quinoline, an isoquinoline, a 2,6-naphthyridine, a 1,8-naphthyridine, a 1,5-naphthyridine, a 1,6-naphthyridine, a 1,7-naphthyridine, a 2,7-naphthyridine, a quinoxaline, a phthalazine, a quinazoline, and a cinnoline;
at least one of A 21 and A 22 is each independently selected from a quinoline, an isoquinoline, a 2,6-naphthyridine, a 1,8-naphthyridine, a 1,5-naphthyridine, a 1,6-naphthyridine, a 1,7-naphthyridine, a 2,7-naphthyridine, a quinoxaline, a phthalazine, a quinazoline, and a cinnoline;
X 11 is N[(L 12 ) a12 -(R 12 ) b12 ];
X 21 is selected from N[(L 22 ) a22 -(R 22 ) b22 ] and C[(L 22 ) a22 -(R 22 ) b22 ][R 26 ];
L 11 to L 13 , and L 71 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;
L 21 and L 22 are each independently selected from groups represented by Formulae 3-1 to 3-19:

wherein in Formulae 3-1 to 3-19,
X 31 is selected from O, S, and C(R 33 )(R 34 );
R 31 to R 34 are each independently selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, iso-butyl group, a sec-butyl group, a tert-butyl group, a phenyl group, and a naphthyl group;
b31 is selected from 1, 2, 3, and 4;
b32 is selected from 1, 2, 3, 4, 5, and 6;
b33 is selected from 1, 2, and 3; and
* and *′ each indicate a binding site to a neighboring atom;
a11 to a13, a21, a22, and a71 are each independently selected from 0, 1, 2, 3, 4, and 5;
R 11 and R 12 are each independently selected from R HT and R ET , and at least one selected from R 11 and R 12 is R ET ;
R 21 and R 22 are each independently R HT ,
provided that when X 21 is N[(L 22 ) a22 -(R 22 ) b22 ], R 21 and R 22 are each independently not a substituted or unsubstituted furanyl group, carbazolyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, thianthrenyl group, phenoxathinyl group, or dibenzodioxinyl group, and
when X 21 is C[(L 22 ) a22 -(R 22 ) b22 ][R 26 ], R 21 is not a substituted or unsubstituted phenyl group or a substituted or unsubstituted fluorenyl group;
R 71 is selected from groups represented by Formulae 6-1 to 6-44 and 6-46 to 6-63 below:

wherein in Formulae 6-1 to 6-44 and 6-46 to 6-63,
R 61 and R 62 are each independently selected from:
deuterium, a C 1 -C 20 alkyl group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a pyridinyl group, —N(Q 41 )(Q 42 ), and —Si(Q 43 )(Q 44 )(Q 45 ); and
a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a pyridinyl group, each substituted with at least one selected from deuterium, a C 1 -C 20 alkyl group, a phenyl group, a naphthyl group, a pyridinyl group, —N(Q 51 )(Q 52 ), and —Si(Q 53 )(Q 54 )(Q 55 );
b61 is selected from 1, 2, 3, and 4; and
b62 is selected from 1, 2, and 3;
b63 is selected from 1, 2, 3, 4, 5, and 6;
b64 is selected from 1, 2, 3, 4, and 5;
b65 is selected from 1 and 2; and
* indicates a binding site to a neighboring atom,
wherein Q 41 to Q 45 and Q 51 to Q 55 are each independently selected from a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a phenyl group, a biphenyl group, a naphthyl group, and a fluorenyl group;
b11, b12, b21, and b22 are each independently selected from 1, 2, 3, and 4;
R 13 to R 16 , R 26 , and R 72 to R 80 are each independently selected from hydrogen, 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 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 monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q 1 )(Q 2 ), —Si(Q 3 )(Q 4 )(Q 5 ), and —B(Q 6 )(Q 7 );
R 23 to R 25 are each independently selected from hydrogen and a phenyl group;
b13 to b16 and b23 to b25 are each independently selected from 1, 2, 3 and 4;
R HT is a hole transport group selected from:
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

Assignees

• Samsung Display Co Ltd

Inventors

• Cho Hwan-Hee
• Kim Myeong-Suk
• Kim Sung-Wook

Classifications

• H01L2251/308

  Electricity · mapped topic

• H01L51/0079

  Electricity · mapped topic

• H01L51/0058

  Electricity · mapped topic

• H01L51/0056

  Electricity · mapped topic

• H01L51/0067

  Electricity · mapped topic