Organic light-emitting device

Patent metadata

Field	Value
Publication number	US-10038147-B2
Application number	US-201514738564-A
Country	US
Kind code	B2
Filing date	Jun 12, 2015
Priority date	Jun 12, 2014
Publication date	Jul 31, 2018
Grant date	Jul 31, 2018

Abstract

An organic light-emitting device includes: a first electrode; a second electrode facing the first 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 electron transport region including an electron transport material represented by Formula 1:

The organic light-emitting device may have low driving voltage, improved efficiency, improved luminance, and improved lifetime.

First claim

What is claimed is:

1. An organic light-emitting device comprising:
a first electrode;
a second electrode facing the first 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, the electron transport region comprising
an electron transport material represented by Formula 1-11:

wherein, in Formula 1-11,
L 1 is selected from:
a phenylene group, and
a phenylene group 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 group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, 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, and a cyclohexenyl group;
a1 is selected from 0 and 1;
R 1 is selected from a phenyl group, a naphthyl group, a pyridinyl group, and a benzimidazolyl group, and
a phenyl group, a naphthyl group, a pyridinyl group, and a benzimidazolyl 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 group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group and a benzimidazolyl group;
R 2 and R 3 are each independently selected from a phenyl group, a naphthyl group, and a pyridinyl group, and
a phenyl group, a naphthyl group, and a pyridinyl 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 group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, and a pyridinyl group; and
R 2 and R 3 are identical to each other;
provided that when R 1 is selected from a substituted or unsubstituted phenyl group and a substituted or unsubstituted naphthyl group, R 2 and R 3 is each a substituted or unsubstituted pyridinyl group, and
when R 2 and R 3 are selected from a substituted or unsubstituted phenyl group and a substituted or unsubstituted naphthyl group, R 1 is selected from a substituted or unsubstituted pyridinyl group and a substituted or unsubstituted benzimidazolyl group.

2. The organic light-emitting device of claim 1 , wherein L 1 is selected from groups represented by Formulae 3-1 and 3-2:

wherein, in Formulae 3-1 and 3-2,
R 31 is 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 group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, and a C 1 -C 20 alkoxy group;
a31 is selected from 1, 2, 3, and 4; and
* and *′ are each independently a binding site with an adjacent atom.

3. The organic light-emitting device of claim 1 , wherein L 1 is selected from groups represented by Formulae 4-1 to 4-5:

wherein, in Formulae 4-1 to 4-5,
* and *′ are each independently a binding site with an adjacent atom.

4. The organic light-emitting device of claim 1 , wherein R 1 is selected from groups represented by Formulae 5-1 to 5-3, 5-10 to 5-12 and 5-46 to 5-51, and R 2 and R 3 are each independently selected from groups represented by Formulae 5-1 to 5-3 and 5-10 to 5-12:

wherein, in Formulae 5-1 to 5-3, 5-10 to 5-12 and 5-46 to 5-51,
R 51 to R 53 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 group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a phenyl group, a naphthyl group, and a pyridinyl group;
a51 is selected from 1, 2, 3, 4, and 5;
a52 is selected from 1, 2, 3, 4, 5, 6, and 7;
a54 is selected from 1, 2, and 3;
a55 is selected from 1, 2, 3, and 4; and
* is a binding site with an adjacent atom.

5. The organic light-emitting device of claim 1 , wherein R 1 is selected from groups represented by Formulae 6-1 to 6-3, 6-6 to 6-40, 6-46 to 6-51, 6-82 and 6-83 and R 2 and R 3 are each independently selected from groups represented by Formulae 6-1 to 6-3, 6-6 to 6-40, and 6-46 to 6-51:

wherein, in Formulae 6-1 to 6-3, 6-6 to 6-40, 6-46 to 6-51, 6-82 and 6-83,
t-Bu is a tert-butyl group; Ph is a phenyl group; and * is a binding site with an adjacent atom.

6. The organic light-emitting device of claim 1 , wherein the electron transport region further includes an alkali metal complex.

7. The organic light-emitting device of claim 6 , wherein the alkali metal complex is represented by one of Formulae 2-1 to 2-4:

wherein, in Formulae 2-1 to 2-4,
M is an alkali metal;
R 21 to R 23 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 group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group 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 grou

Assignees

• Samsung Display Co Ltd
• Nat Univ Gyeongsang Iacf

Inventors

• Kim Mikyung
• Kwon Soonki
• Kim Yunhi

Classifications

• H01L51/5072

  Electricity · mapped topic

• H01L51/0058

  Electricity · mapped topic

• H01L51/0072 Primary

  Electricity · mapped topic

• H01L2251/308

  Electricity · mapped topic

• H01L51/0067

  Electricity · mapped topic