Organic light-emitting device

Patent metadata

Field	Value
Publication number	US-12262629-B2
Application number	US-202217811211-A
Country	US
Kind code	B2
Filing date	Jul 7, 2022
Priority date	Jul 19, 2017
Publication date	Mar 25, 2025
Grant date	Mar 25, 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. The organic layer includes a first compound represented by Formula 1 and a second compound represented by Formula 2. The first compound may be included in an emission layer, and the second compound may be included in an electron transport region.

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 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-A and the electron transport region comprises a second compound represented by Compounds 2-2 to 2-70:

wherein, in Formula 1-A,
M is platinum (Pt),
X 51 is selected from the group consisting of O, S, and N—R 7 ,
L 1 to L 4 are each independently a benzene group,
b1 to b4 are each 0,
R 1 is hydrogen, or an unsubstituted benzene group,
R 2 is a tert-butyl group,
R 3 is hydrogen, a tert-butyl group, or an unsubstituted benzene group,
R 4 is a tert-butyl group, or a benzene group substituted with an isopropyl group, and
R 7 is an unsubstituted benzene group, or a benzene group substituted with a tert-butyl group,
c1 to c4 are each 1,
a1 to a4 are each independently 0 or 1,

2. The organic light-emitting device of claim 1 , wherein the first compound is a compound represented by one of Formulae 1-1 to 1-3:

wherein, in Formulae 1-1 to 1-3,
L 1 to L 4 , b1 to b4, R 1 to R 4 , R 7 , c1 to c4, and a1 to a4 are each independently the same as described in connection with Formula 1-A.

3. The organic light-emitting device of claim 1 , wherein
the emission layer further comprises a host, and
an amount of the host comprised in the emission layer is larger than an amount of the first compound.

4. The organic light-emitting device of claim 1 , wherein
the electron transport region comprises an electron transport layer and an electron injection layer, and
at least one of the electron transport layer or the electron injection layer further comprises a metal-containing material.

5. The organic light-emitting device of claim 4 , wherein
the metal-containing material comprises at least one selected from an alkali metal complex, an alkaline earth-metal complex, and a rare earth metal complex,
a metal ion of the alkali metal complex is a Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion,
a metal ion of the alkaline earth-metal complex is a Mg ion or a Ca ion, and
a metal ion of the rare earth metal complex is an Er ion, a Tm ion, or a Yb ion.

6. The organic light-emitting device of claim 1 , wherein
the organic layer further comprises a hole transport region between the emission layer and the first electrode, and
the hole transport region comprises a compound represented by Formula 201A:

wherein, in Formula 201A,
L 201 to L 203 are each independently selected from the group consisting of:
a phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorene group, a dibenzofluorene group, a phenanthrenylene group, an anthracenylene group, a pyrenylene group, a chrysenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a quinolinylene group, an isoquinolinylene group, a quinoxalinylene group, a quinazolinylene group, a carbazolylene group, and a triazinylene group; and
a phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a pyrenylene group, a chrysenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a quinolinylene group, an isoquinolinylene group, a quinoxalinylene group, a quinazolinylene group, a carbazolylene group, and a triazinylene group, each substituted with at least one selected from the group consisting of 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 fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group,
xa1 to xa3 are each independently 0, 1, or 2,
R 203 and R 211 are each independently selected from the group consisting of:
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 pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group; and
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 pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group, each substituted with at least one selected from the group consisting of 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, an azulenyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group, and
R 213 to R 216 are each independently hydrogen, deuterium, a methyl group, or a phenyl group.

7. A flat-panel display apparatus comprising:
a thin film transistor comprising a source electrode, a drain electrode,

Assignees

• Samsung Display Co Ltd

Inventors

• Bae Sung-Soo
• Kim Seul-Ong
• Kim Dong-Hyun
• Kim Sung-Wook
• Naijo Tsuyoshi
• Jeong Hye-In
• Cho Hwan-Hee

Classifications

• H10K2101/10

  Triplet emission · CPC title

• H10K85/654

  comprising only nitrogen as heteroatom (H10K85/652 takes precedence) · CPC title

• H10K85/636

  comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom · CPC title

• H10K85/626

  containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene · CPC title

• H10K50/171

  Electron injection layers · CPC title