Organic light-emitting device and method of manufacturing the same

Patent metadata

Field	Value
Publication number	US-11903310-B2
Application number	US-202016945444-A
Country	US
Kind code	B2
Filing date	Jul 31, 2020
Priority date	Nov 5, 2019
Publication date	Feb 13, 2024
Grant date	Feb 13, 2024

Abstract

An organic light-emitting includes a first electrode having a work function greater than about 4.9 eV and less than about 5.2 eV, a second electrode facing the first electrode, an organic layer disposed between the first electrode and the second electrode and including an emission layer, a hole transport region disposed between the first electrode and the emission layer, wherein the hole transport region includes a first hole transport layer including a first hole-transporting material, and the first hole transport layer is substantially free of a p-dopant.

First claim

What is claimed is:

1. An organic light-emitting device comprising:
a first electrode having a work function greater than about 4.9 eV and less than about 5.2 eV;
a second electrode facing the first electrode;
an organic layer disposed between the first electrode and the second electrode and comprising an emission layer;
a hole transport region disposed between the first electrode and the emission layer;
wherein the hole transport region comprises a first hole transport layer comprising a first hole-transporting material and a second transport layer disposed between the first hole transport layer and the emission layer;
the first hole transport layer is substantially free of a p-dopant,
the second hold transport layer comprises a second hole-transporting material different from the first hole-transporting material, and
the second hole-transporting material comprises a compound of Formula 202-2 below:

wherein in Formula 202-2,
L 223 to L 225 are each, independently from one another, 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 fused polycyclic group, or a substituted or unsubstituted divalent non-aromatic fused heteropolycyclic group;
xa23 to xa24 are each, independently from one another, an integer from 0 to 3;
xa25 is an integer from 1 to 10;
Ar 223 to Ar 224 are each, independently from one another, 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 fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group;
R 221 and R 222 are each, independently from one another, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone 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 C3-Cia 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 fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 )(Q 2 ), or —P(═O)(Q 1 )(Q 2 );
xb21 and xb22 are each, independently from one another, an integer from 1 to 4; and Q 1 to Q 3 are each, independently from one another, 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 C 1 -C 60 alkyl group, a C 2 -C 60 alkenyl group, a C 2 -C 60 alkynyl group, a C 1 -C 60 alkoxy group, a C 3 -C 10 cycloalkyl group, a C 1 -C 10 heterocycloalkyl group, a C 3 -C 10 cycloalkenyl group, a C 1 -C 10 heterocycloalkenyl group, a C 6 -C 60 aryl group, a C 1 -C 60 heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, a biphenyl group, or a terphenyl group.

2. The organic light-emitting device of claim 1 , wherein the first hole transport layer directly contacts the first electrode.

3. The organic light-emitting device of claim 1 , wherein the first hole-transporting material comprises a compound represented by Formula 201 below:

wherein, in Formula 201,
X 211 is N(R 211a ) or C(R 211a )(R 211b );
L 211 to L 213 are each, independently from one another, 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 10 arylene group, a substituted or unsubstituted C 1 -C 60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic fused polycyclic group, or a substituted or unsubstituted divalent non-aromatic fused heteropolycyclic group;
xa1 to xa3 are each, independently from one another, an integer from 0 to 3;
R 211a , R 211b , and R 212 are each, independently from one another, 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 fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group;
R 211a and R 211b are optionally linked together to form an unsubstituted or substituted C 5 -C 60 carbocyclic ring or a C 1 -C 60 heterocyclic ring;
R 213 to R 218 are each, independently from one another, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone 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 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 fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, —Si(Q 1 )(Q 2 )(Q 3 ), —N(Q 1 )(Q 2 ), —B(Q 1 )(Q 2 ), —C(═O)(Q 1 ), —S(═O) 2 (Q 1 )(Q 2 ), or —P(═O)(Q 1 )(Q 2 );
xb5 and xb7 are each, independently from one another, an integer from 1 to 4;
xb6 and xb8 are each, independently from one another, an integer from 1 to 3; and

Assignees

• Samsung Display Co Ltd

Inventors

• Kim Hyoungkun
• Kho Samil
• Kim Donghwan
• Kim Jinwoong
• Yang Seunggak
• Lee Kwanhee
• Lee Junyoung

Classifications

• H10K85/6572 Primary

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• H10K85/636 Primary

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

• H10K71/00

  Manufacture or treatment specially adapted for the organic devices covered by this subclass · CPC title

• H10K50/805

  Electrodes · CPC title

• H10K85/6574

  comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes · CPC title