Organic light emitting device

Patent metadata

Field	Value
Publication number	US-11515480-B2
Application number	US-201916721777-A
Country	US
Kind code	B2
Filing date	Dec 19, 2019
Priority date	Dec 21, 2018
Publication date	Nov 29, 2022
Grant date	Nov 29, 2022

Abstract

The present disclosure provides an organic light-emitting device comprising a novel compound. When the novel compound is applied as a hole transport material to an organic light emitting device, the novel compound allows the device to have improved drive voltage, efficiency and lifespan characteristics.

First claim

What is claimed is:

1. An organic light-emitting device, comprising:
a first electrode;
a second electrode; and
at least one organic material layer between the first and second electrodes,
wherein the at least one organic material layer contains a compound represented by the following Chemical Formula 1:

wherein:
X represents O or S,
each of R1 and R2 independently represents a substituent selected from the group consisting of an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 carbon atoms, an alkyl group having 1 to 15 carbon atoms, a halogen atom, and a deuterium atom,
a is an integer from 0 to 4, provided that when a is 2 or more, the corresponding R1 is the same as or different from each other, or adjacent corresponding R1s are bonded to each other to form a ring,
b is an integer from 0 to 3, provided that when b is 2 or more, the corresponding R2 is the same as or different from each other, or adjacent corresponding R2s are bonded to each other to form a ring,
n is 0 or 1, n=0 representing a direct bond,
m is an integer of 1 to 3,
each of c and d is independently an integer of 0 or 1,
m, c and d are selected such that when m is 1, c+d=2, when m is 2, c+d=1, and when m is 3, c+d=0, and
each of Ar1 and Ar2 independently represents one selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an alkoxyl group having 1 to 30 carbon atoms, and an aryloxy group having 6 to 30 carbon atoms,

wherein the at least one organic material layer includes at least one layer selected from the group consisting of a hole transport layer and an auxiliary hole transport layer, and
wherein the at least one layer contains at least two types of the compounds represented by Chemical Formula 1.

2. An organic light-emitting device, comprising:
a first electrode;
a second electrode; and
at least one organic material layer between the first and second electrodes,
wherein the at least one organic material contains a.A compound represented by the following Chemical Formula 1-1:

wherein:
X represents S,
each of R1 and R2 independently represents a substituent selected from the group consisting of an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 carbon atoms, an alkyl group having 1 to 15 carbon atoms, a halogen atom, and a deuterium atom,
a is an integer from 0 to 4, provided that when a is 2 or more, the corresponding R1 is the same as or different from each other, or adjacent corresponding Rls are bonded to each other to form a ring,
b is an integer from 0 to 3, provided that when b is 2 or more, the corresponding R2 is the same as or different from each other, or adjacent corresponding R2s are bonded to each other to form a ring,
n is 0 or 1, n=0 representing a direct bond,
m is an integer of 1 to 3,
each of c and d is independently an integer of 0 or 1,
m, c and d are selected such that m+c+d=3, and
each of Ar1 and Ar2 independently represents one selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an alkoxyl group having 1 to 30 carbon atoms, and an aryloxy group having 6 to 30 carbon atoms,
with the proviso that each of R1, R2, Ar1 and Ar2 is independently not carbazole or free of a carbazole substituent,

wherein the at least one organic material layer includes at least one layer selected from the group consisting of a hole transport layer and an auxiliary hole transport layer, and
wherein the at least one layer contains at least two types of the compounds represented by Chemical Formula 1-1.

3. The organic light-emitting device of claim 1 , wherein the compound is represented by the following Chemical Formula 2:

wherein:
X represents O or S,
each of R1 and R2 independently represents a substituent selected from the group consisting of an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 carbon atoms, an alkyl group having 1 to 15 carbon atoms, a halogen atom, and a deuterium atom,
a is an integer from 0 to 4, provided that when a is 2 or more, the corresponding R1 is the same as or different from each other, or adjacent corresponding R1s are bonded to each other to form a ring,

b is an integer from 0 to 3, provided that when b is 2 or more, the corresponding R2 is the same as or different from each other, or adjacent corresponding R2s are bonded to each other to form a ring,
m is an integer of 1 to 3,
each of c and d is independently an integer of 0 or 1,
m, c and d are selected such that when m is 1, c+d=2, when m is 2, c+d=1, and when m is 3, c+d=0, and
each of Ar1 and Ar2 independently represents one selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an alkoxyl group having 1 to 30 carbon atoms, and an aryloxy group having 6 to 30 carbon atoms.

4. The organic light-emitting device of claim 1 , wherein the compound is represented by one of the following Chemical Formulas 3 to 5:

wherein:
X represents 0 or S,
each of R1 and R2 independently represents a substituent selected from the group consisting of an aryl group having 6 to 30 carbon atoms, a heteroaryl group having 5 to 30 carbon atoms, an alkyl group having 1 to 15 carbon atoms, a halogen atom, and a deuterium atom,
a is an integer from 0 to 4, provided that when a is 2 or more, the corresponding R1 is the same as or different from each other, or adjacent corresponding Rls are bonded to each other to form a ring,
b is an integer from 0 to 3, provided that when b is 2 or more, the corresponding R2 is the same as or different from each other, or adjacent corresponding R2s are bonded to each other to form a ring,
m is an integer of 1 to 3,
each of c and d is independently an integer of 0 or 1,
m, c and d are selected such that when m is 1, c+d=2, when m is 2, c+d=1, and when m is 3, c+d=0, and
each of Ar1 and Ar2 independently represents one selected from the group consisting of a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an alkoxyl group having 1 to 30 carbon atoms, and an aryloxy group having 6 to 30 carbon atoms.

5. The organic light-emitting device of claim 1 , wherein each of Ar1 and Ar2 of the Chemical Formula 1 is independently selected from the following substituents:

6. The organic light-emitting device of claim 1 , wherein the compound is repre

Assignees

• Lg Display Co Ltd

Inventors

• Park Heejun
• Yoo Seonkeun
• Jang Soyoung
• Shin Jicheol
• Kim Sangbeom
• Kim Sunghoon
• Lee Tae Wan
• Lee Dong Hun
• Heo Jeonghoe

Classifications

• C07D333/76 Primary

  Dibenzothiophenes · CPC title

• C07D409/14

  containing three or more hetero rings · CPC title

• H01L27/3244

  Electricity · mapped topic

• H01L51/5012

  Electricity · mapped topic

• H01L2251/558

  Electricity · mapped topic