Polymer, monomer, coating composition comprising same, organic light emitting device using same, and method for manufacturing organic light emitting device by using same

Patent metadata

Field	Value
Publication number	US-12304977-B2
Application number	US-202017621007-A
Country	US
Kind code	B2
Filing date	Sep 18, 2020
Priority date	Sep 19, 2019
Publication date	May 20, 2025
Grant date	May 20, 2025

Abstract

The present specification relates to a polymer comprising a unit represented by Chemical Formula 1, a monomer represented by Chemical Formula 2, a coating composition comprising the same, an organic light emitting device formed using the same, and a method for manufacturing an organic light emitting device using the same:wherein the variables are described herein.

First claim

The invention claimed is:

1. A polymer comprising a unit represented by the following Chemical Formula 1:

wherein, in Chemical Formula 1,
L is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group;
a is an integer of 0 to 3, and when a is 2 or greater, Ls are the same as or different from each other;
Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group;
R1 to R4, R4′ and R4″ are the same as or different from each other, and each independently hydrogen; deuterium; a halogen group; a hydroxyl group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group;
R5 to R8 are the same as or different from each other, and each independently deuterium; a halogen group; a hydroxyl group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group;
r6 and r7 are the same as or different from each other, and each independently an integer of 0 to 3, and when r6 is 2 or 3, R6s are the same as or different from each other, and when r7 is 2 or 3, R7s are the same as or different from each other;
r5 and r8 are the same as or different from each other, and each independently an integer of 0 to 4, and when r5 is 2 to 4, R5s are the same as or different from each other, and when r8 is 2 to 4, R8s are the same as or different from each other; and
n is, as a repetition number of the unit, an integer of 2 to 10,000,
wherein the polymer is a homopolymer.

2. The polymer of claim 1 , wherein the unit is represented by Chemical Formula 1-1:

in Chemical Formula 1-1,
R1 to R8, R4′, R4″, L, Ar1, Ar2, r5 to r8, n and a have the same definitions as in Chemical Formula 1.

3. The polymer of claim 1 , wherein L is a direct bond; or any one selected from among the following structures:

in the structures,
R is an aryl group;
R′ and R″ are the same as or different from each other, and each independently hydrogen; or
an alkyl group; and
the structures are each optionally further substituted with an alkyl group.

4. The polymer of claim 1 , wherein Ar1 and Ar2 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with an aryl group; an aryl group substituted with a heteroaryl group; an aryl group substituted with an alkyl group; an aryl group substituted with an aryl group substituted with an alkyl group; an aryl group substituted with a heteroaryl group substituted with an aryl group; or a heteroaryl group unsubstituted or substituted with an aryl group.

5. A coating composition comprising the polymer of claim 1 .

6. The coating composition of claim 5 , wherein a content of the polymer comprising the unit represented by Chemical Formula 1 in the coating composition is from 0.1 wt/v % to 20 wt/v %.

7. A method for manufacturing an organic light emitting device, the method comprising:
preparing a first electrode;
forming an organic material layer on the first electrode; and
forming a second electrode on the organic material layer,
wherein the forming of an organic material layer comprises forming the organic material layer using the coating composition of claim 5 ; and
the forming of the organic material layer using the coating composition comprises coating the coating composition on the first electrode; and heat treating or light treating the coated coating composition.

8. An organic light emitting device comprising:
a first electrode;
a second electrode; and
an organic material layer provided between the first electrode and the second electrode,
wherein the organic material layer comprises the polymer of claim 1 .

9. The organic light emitting device of claim 8 , wherein the organic material layer comprising the polymer is an electron blocking layer; a hole transfer layer; a hole injection layer; or a layer carrying out hole transfer and hole injection at the same time.

10. The organic light emitting device of claim 8 , wherein the organic material layer comprising the polymer is a hole blocking layer; an electron transfer layer; an electron injection layer; or a layer carrying out electron transfer and electron injection at the same time.

11. The organic light emitting device of claim 8 , wherein the organic material layer comprising the polymer has solubility of 0.05 wt % or less for cyclohexanone.

12. A method for manufacturing an organic light emitting device, the method comprising:
preparing a first electrode;
forming an organic material layer on the first electrode; and
forming a second electrode on the organic material layer,
wherein the forming of the organic material layer comprises forming the organic material layer using the coating composition comprising the polymer of claim 1 ; and
the forming of the organic material layer using the coating composition comprises coating the coating composition on the first electrode; and heat treating or light treating the coated coating composition.

13. The polymer of claim 1 , wherein the polymer has a number average molecular weight of 5,000 g/mol to 1,000,000 g/mol.

14. A coating composition comprising a monomer represented by Chemical Formula 2 and a solvent:

wherein, in Chemical Formula 2,
L is a direct bond; a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group;
a is an integer of 0 to 3, and when a is 2 or greater, Ls are the same as or different from each other;
Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group;
R1 to R4, R4′ and R4″ are the same as or different from each other, and each independently hydrogen; deuterium; a halogen group; a hydroxyl group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group;
R5 to R8 are the same as or different from each other, and each independently deuterium; a halogen group; a hydroxyl group; a cyano group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group;
r6 and r7 are the same as or different from each other, and each independently an integer of 0 to 3, and when r6 is 2 or 3, R6s are the same as or different from each other, and when r7 is 2 or 3, R7s are the same as or different from each other; and

Assignees

• Lg Chemical Ltd

Inventors

• Jung Min Suk
• Bae Jaesoon
• Park Youngju
• Kang Esder
• Lim Byeong Yun
• Lim Dowon
• Lee Jaechol
• Choi Hyunju

Classifications

• H10K50/181

  Electron blocking layers · CPC title

• H10K50/18

  Carrier blocking layers · CPC title

• H10K85/6574

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

• H10K85/6572

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

• H10K85/631

  Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine · CPC title