Copolymer and organic light emitting device comprising same

Patent metadata

Field	Value
Publication number	US-11309494-B2
Application number	US-201816615535-A
Country	US
Kind code	B2
Filing date	Oct 17, 2018
Priority date	Oct 30, 2017
Publication date	Apr 19, 2022
Grant date	Apr 19, 2022

Abstract

The present specification provides a copolymer including a unit of Chemical Formula 1 and a unit of Chemical Formula 2; and an organic light emitting device including the same.

First claim

The invention claimed is:

1. A copolymer comprising:
a unit of the following Chemical Formula 1;
a unit of the following Chemical Formula 2; and
a unit of the following Chemical Formula 3,

wherein, in Chemical Formulae 1 and 2,
Y1 is O;
R1 is hydrogen; deuterium; a halogen group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted cycloalkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heterocyclic group;
Ar1 to Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted arylene group; or a substituted or unsubstituted heteroarylene group;
Ar4 and Ar5 are the same as or different from each other, and each independently hydrogen;
deuterium; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group;
Ar6 is a direct bond;
Ar7 is a substituted or unsubstituted arylene group;
Ar8 and Ar9 are the same as or different from each other, and each independently hydrogen;
deuterium; a halogen group; a nitrile group; a substituted or unsubstituted silyl group; a substituted or unsubstituted alkoxy group; a substituted or unsubstituted aryloxy group; a substituted or unsubstituted amine group; a substituted or unsubstituted alkyl group; a substituted or unsubstituted aryl group; or a substituted or unsubstituted heteroaryl group;
a is an integer of 0 to 3;
b is an integer of 0 or 1;
c is an integer of 0 to 10;
e is an integer of 1 or 2; and
f is an integer of 1 or 2;
when a is greater than 1, each of R1 is the same as or different from each other;
when e is 2, each of

is the same as or different from each other; and
when f is 2, each of

is the same as or different from each other,

wherein, in Chemical Formula 3,
R2 and R3 are the same as or different from each other, and each independently an unsubstituted alkyl group;
R4 is hydrogen; deuterium; a halogen group; or a substituted or unsubstituted alkyl group; and
d is from 0 to 6;
when d is greater than 1, each of R4 is the same as or different from each other.

2. The copolymer of claim 1 , comprising one, two or more of units represented by the following Chemical Formula 1-1 or Chemical Formula 1-2:

wherein, in Chemical Formulae 1-1 and 1-2,
R1 to R4, Ar1 to Ar9, Y1, and a to f have the same definitions as in Chemical Formulae 1 to 3.

3. The copolymer of claim 1 , which is any one of the following structures:

wherein, in the structural formulae,
and p are a molar ratio of each represented unit, and o+p=1,
is a molar ratio of 0.05 to 0.95, and p is a molar ratio of 0.05 to 0.95.

4. The copolymer of claim 1 , which has a number average molecular weight of 1,000 g/mol to 1,000,000 g/mol.

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

6. An organic light emitting device comprising:
a first electrode;
a second electrode provided opposite to the first electrode; and
one or more organic material layers between the first electrode and the second electrode,
wherein one or more layers of the organic material layers include the coating composition of claim 5 or a cured material thereof.

7. The organic light emitting device of claim 6 , wherein the organic material layer includes a hole transfer layer, a hole injection layer, or a layer carrying out hole transfer and hole injection at the same time; and
the hole transfer layer, the hole injection layer, or the layer carrying out hole transfer and hole injection at the same time includes the coating composition or a cured material thereof.

8. The organic light emitting device of claim 6 , wherein the organic material layer includes an electron injection layer, an electron transfer layer, or a layer carrying out electron injection and electron transfer at the same time; and
the electron injection layer, the electron transfer layer, or the layer carrying out electron injection and electron transfer at the same time includes the coating composition or a cured material thereof.

9. A method for manufacturing an organic light emitting device comprising:
preparing a substrate;
forming a cathode or an anode on the substrate;
forming one or more organic material layers on the cathode or the anode; and
forming an anode or a cathode on the organic material layer,
wherein the forming of organic material layers includes forming one or more organic material layers using the coating composition of claim 5 .

10. The method for manufacturing an organic light emitting device claim 9 , wherein the forming of one or more organic material layers formed using the coating composition includes drying after coating the coating composition.

11. The copolymer of claim 1 , wherein R1 and R4 are hydrogen; R2 and R3 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; Ar1 to Ar3 are a phenylene group; Ar4 and Ar5 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an alkyl group; Ar6 is a direct bond; Ar7 is a phenylene group unsubstituted or substituted with a methyl group or F, or a fluorenylene group unsubstituted or substituted with a methyl group or a phenyl group; and Ar8 and Ar9 are hydrogen.

12. The copolymer of claim 1 , which includes a structure represented by represented by the following Chemical Formula 1-3:

wherein, in Chemical Formula 1-3,
R1 to R4, Ar1 to Ar9, Y1, and a to f have the same definitions as in Chemical Formulae 1 to 3,
and p are a molar ratio of each represented unit, and o+p=1,
is a molar ratio of 0.05 to 0.95, and
p is a molar ratio of 0.05 to 0.95.

13. The copolymer of claim 1 , wherein an end group of the copolymer is hydrogen or an alkyl group.

14. The coating composition of claim 5 , wherein the copolymer is in a range of 1% by weight to 10% by weight.

Assignees

• Lg Chemical Ltd

Inventors

• Yi Yeonhui
• Kim Jinseck
• Bae Jaesoon
• Lee Jaechol
• Yu Soyoung
• Jeong Jae Hak

Classifications

• C08G2261/1414

  Unsaturated aliphatic units · CPC title

• C08G2261/12

  Copolymers · CPC title

• C08G2261/3142

  fluorene-based, e.g. fluorene, indenofluorene, or spirobifluorene · CPC title

• C08G2261/3162

  Arylamines · CPC title

• H10K71/00

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