Polyfluorene-based polymer-polyvinylidene fluoride graft copolymer and element including the same

Patent metadata

Field	Value
Publication number	US-11370864-B2
Application number	US-202017106427-A
Country	US
Kind code	B2
Filing date	Nov 30, 2020
Priority date	Jul 27, 2020
Publication date	Jun 28, 2022
Grant date	Jun 28, 2022

Abstract

Disclosed is a graft copolymer containing a polyfluorene-based polymer as a main chain and a polyvinylidene fluoride (PVDF) as a side chain, and an element including the same. The graft copolymer contains both the polyfluorene-based polymer and the PVDF, so that the graft copolymer may increase miscibility between polymers to prepare a composite having excellent performance, prepare an uniform thin film through a solution process, and be used as a single material that exhibits both piezoelectric properties and luminescence properties.

First claim

The invention claimed is:

1. A polyfluorene-based polymer-polyvinylidene fluoride graft copolymer represented by the following Formula 1:

wherein
R 1 and R 2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,
R 3 and R 4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
R 5 is a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms,
R 6 and R 7 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkyl xanthate group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
a, b, c, and d are each independently an integer of 1 to 3, and
n is an integer of 1 to 5.

2. The polyfluorene-based polymer-polyvinylidene fluoride graft copolymer of claim 1 , wherein R 1 and R 2 are each independently a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

3. The polyfluorene-based polymer-polyvinylidene fluoride graft copolymer of claim 2 , wherein R 1 and R 2 are each independently a substituted or unsubstituted phenyl group.

4. The polyfluorene-based polymer-polyvinylidene fluoride graft copolymer of claim 1 , wherein R 3 and R 4 are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms.

5. The polyfluorene-based polymer-polyvinylidene fluoride graft copolymer of claim 1 , wherein R 5 is a direct linkage or a heteroarylene group, wherein the heteroarylene group is unsubstituted or substituted by a halogen atom or an alkyl group having 1 to 10 carbon atoms, and has 2 to 30 ring carbon atoms and 1 to 4 heteroatoms, wherein the heteroatom is one or more selected from N and S.

6. The polyfluorene-based polymer-polyvinylidene fluoride graft copolymer of claim 5 , wherein R 5 is a direct linkage, or a substituted or unsubstituted benzothiadiazolylene group or a substituted or an unsubstituted benzothiadiazolylene group in which a substituted or unsubstituted thiophenyl group is linked to both sides.

7. The polyfluorene-based polymer-polyvinylidene fluoride graft copolymer of claim 1 , wherein R 6 and R 7 are each independently an alkyl xanthate group which has 1 to 10 carbon atoms and is unsubstituted or substituted by a halogen atom or an alkyl group having 1 to 10 carbon atoms.

8. The polyfluorene-based polymer-polyvinylidene fluoride graft copolymer of claim 7 , wherein R 6 and R 7 are the same as each other, and are an alkyl xanthate group having 1 to 10 carbon atoms substituted by a halogen atom.

9. The polyfluorene-based polymer-polyvinylidene fluoride graft copolymer of claim 1 , wherein Formula 1 is represented by any one of the following Formulas 1-1 to 1-3:

wherein
R 1 to R 4 , a to d, and n are as defined in Formula 1.

10. The polyfluorene-based polymer-polyvinylidene fluoride graft copolymer of claim 1 , wherein Formula 1 is represented by any one of the following Formulas 1-4 to 1-6:

wherein
c, d, and n are as defined in claim 1 .

11. An element, comprising:
a substrate;
a first electrode disposed on the substrate;
a light emitting layer disposed on the first electrode; and
a second electrode disposed on the light emitting layer,
wherein the light emitting layer includes a polyfluorene-based polymer-polyvinylidene fluoride graft copolymer represented by the following Formula 1:

wherein
R 1 and R 2 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 2 to 30 ring carbon atoms,
R 3 and R 4 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
R 5 is a direct linkage, a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroarylene group having 2 to 30 ring carbon atoms,
R 6 and R 7 are each independently a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkyl xanthate group, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
a, b, c, and d are each independently an integer of 1 to 3, and
n is an integer of 1 to 5.

12. The element of claim 11 , wherein Formula 1 is represented by any one of the following Formulas 1-4 to 1-6:

wherein
c, d, and n are as defined in claim 8 .

13. The element of claim 11 , wherein
a copolymer represented by Formula 1-4 emits blue light,
a copolymer represented by Formula 1-5 emits green light, and
a copolymer represented by Formula 1-6 emits red light.

14. The element of claim 11 , wherein the substrate is a flexible substrate.

15. The element of claim 11 , wherein the element exhibits both piezoelectricity and luminescence.

16. The element of claim 11 , wherein the element is used for a wearable electronic element, an electronic skin, or an electronic element for a vehicle.

Assignees

• Univ Yonsei Iacf

Inventors

• Lee Jinkyun
• Lee Sejin
• Kim Jiyeon
• Park Cheolmin
• Kim Euihyuk
• Bang Joona

Classifications

• H10H20/822

  Materials of the light-emitting regions · CPC title

• C08G2261/122

  statistical · CPC title

• C08J5/18

  Manufacture of films or sheets · CPC title

• C08F8/36

  Sulfonation; Sulfation · CPC title

• C08G2261/145

  Side-chains containing sulfur · CPC title