# US 11,299,648 B2 · Polymer, coating composition comprising same, and organic light emitting diode using same

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- Number: US 11,299,648 B2
- Document ID: US11299648B2
- Status: Granted
- Kind: B2
- Application number: 16/649,837
- Filed: 2019-02-26
- Published: 2020-09-03
- Granted: 2022-04-12
- Earliest claimed: 2018-02-28
- Assignees: LG Chem, Ltd.
- Applicants: LG Chem, Ltd.
- Inventors: Esder Kang; Jaesoon Bae; Jaechol Lee; Sungkyoung Kang; Hyeonah Shin; Keunsoo Lee; Hyungil Park
- Web page: https://patentgrep.com/patent/US11299648B2

## CPC

- C09D 125/18: Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen
- C08F 212/22: {Oxygen}
- C08F 212/26: {Nitrogen}
- C08F 212/32: containing two or more rings
- H10K 71/40: Thermal treatment, e.g. annealing in the presence of a solvent vapour
- H10K 85/141: {comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE}
- H10K 85/151: {Copolymers}
- H10K 50/11: characterised by the electroluminescent [EL] layers
- H10K 50/15: Hole transporting layers
- H10K 50/17: Carrier injection layers
- H10K 71/13: using printing techniques, e.g. ink-jet printing or screen printing
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- H10K: ORGANIC ELECTRIC SOLID-STATE DEVICES

## Abstract

The present specification relates to a polymer comprising: a first unit represented by Formula 1; and a second unit represented by Formula 2, a coating composition comprising the same, and an organic light emitting device formed by using the same.

## Claims

### Claim 1

A polymer comprising:
a first unit represented by the following Formula 1; and
a second unit represented by the following Formula 2:
in Formulae 1 and 2,
X is a curing group,
L1 to L5 are the same as or different from each other, and are each independently a direct bond; —O—; a substituted or unsubstituted alkylene group; a substituted or unsubstituted arylene group; a substituted or unsubstituted divalent amine group; or a substituted or unsubstituted heteroarylene group,
b1 and b2 are the same as or different from each other, and are each independently an integer from 1 to 10,
when b1 and b2 are each 2 or more, two or more L1s and L5s are each the same as or different from each other,
Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group,
R1 to R9 are the same as or different from each other, and are each independently hydrogen; deuterium; a halogen group; a hydroxyl group; a nitrile group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group,
r4 is an integer from 1 to 5,
r5 is an integer from 1 to 4,
r6 is an integer from 1 to 3,
when r4 to r6 are each 2 or more, two or more R4s to R6s are each the same as or different from each other,
m1 is a mole fraction and 0<m1<1,
m2 is a mole fraction and 0<m2<1, and
m1+m2≤1.

### Claim 2 (depends on 1)

The polymer of claim 1, wherein X is any one selected from the following structures:
in the structures,
L11 is a substituted or unsubstituted alkylene group; or a substituted or unsubstituted arylene group, and
R10 to R13 are the same as or different from each other, and are each independently hydrogen; or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.

### Claim 3 (depends on 1)

The polymer of claim 1, wherein the first unit represented by Formula 1 is represented by any one of the following structures:
in the structures,
m1 is a mole fraction and 0<m1<1.

### Claim 4 (depends on 1)

The polymer of claim 1, wherein the second unit represented by Formula 2 is represented by any one of the following structures:
in the structures,
m2 is a mole fraction and 0<m2<1.

### Claim 5 (depends on 1)

The polymer of claim 1, wherein the polymer comprising the first unit represented by Formula 1 and the second unit represented by Formula 2 is any one selected from the following structures:
in the structures,
m1 is a mole fraction and 0<m1<1,
m2 is a mole fraction and 0<m2<1,
m1+m2≤1, and
n is a repeating number of the unit, and an integer from 1 to 10,000.

### Claim 6 (depends on 1)

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.

### Claim 7 (depends on 1)

A coating composition comprising the polymer according to claim 1.

### Claim 8 (depends on 7)

The coating composition of claim 7, further comprising:
a p-doping material.

### Claim 9 (depends on 7)

An organic light emitting device comprising:
a first electrode;
a second electrode provided to face the first electrode; and
an organic material layer having at least one layer provided between the first electrode and the second electrode,
wherein the at least one layer comprises a cured product of the coating composition of claim 7.

### Claim 10 (depends on 9)

The organic light emitting device of claim 9, wherein the cured product of the coating composition is in a state in which the coating composition is cured by a heat treatment or a light treatment.

### Claim 11 (depends on 9)

The organic light emitting device of claim 9, wherein the at least one layer comprising the cured product of the coating composition is a hole transport layer, a hole injection layer, or a layer which simultaneously transports and injects holes.

### Claim 12 (depends on 9)

The organic light emitting device of claim 9, wherein the at least one layer comprising the cured product of the coating composition comprises a light emitting layer, and the light emitting layer comprises the cured product of the coating composition.

### Claim 13 (depends on 1)

The polymer of claim 1, wherein in Formulae 1 and 2, m1>m2.

### Claim 14 (depends on 1)

The polymer of claim 1, wherein in Formula 2, X is cyclobutabenzene or oxetane.

### Claim 15 (depends on 7)

The coating composition of claim 7, further comprising a solvent having a boiling point of 40° C. to 250° C.

### Claim 16 (depends on 7)

A method for manufacturing an organic light emitting device, the method comprising:
preparing a substrate;
forming a cathode or an anode on the substrate;
forming an organic material layer having at least one layer on the cathode or the anode; and
forming an anode or a cathode on the organic material layer,
wherein the at least one layer is formed by using the coating composition of claim 7.

### Claim 17 (depends on 16)

The method of claim 16, wherein the at least one layer is formed by a printing method.

### Claim 18 (depends on 16)

The method of claim 16, wherein the forming the organic material layer on the cathode or the anode comprises:
coating the cathode or the anode with the coating composition; and
subjecting the coating composition to a heat treatment or a light treatment.