Polyimide precursor, polyimide precursor composition, polyimide film, manufacturing method thereof, and use thereof
View Patent ↗The present invention relates to a polyimide precursor, a polyimide precursor solution, a polyimide film, a manufacturing method thereof, and a use thereof. The polyimide precursor according to the present invention may provide a polyimide film that has excellent heat resistance and satisfies transparency and a low coefficient of linear thermal expansion, and thus the polyimide film will be usefully applicable in the field of flexible displays requiring high dimensional stability.
1. A polyimide precursor comprising a structural unit derived from an acid dianhydride and a structural unit derived from a diamine compound represented by the following Formula 1:
wherein
A is O or S;
R 1 and R 2 are each independently halogen, (C 1 -C 10 ) alkyl, halo(C 1 -C 10 )alkyl, (C 1 -C 10 )alkoxy, or (C 6 -C 12 ) aryl; and
m and n are each independently an integer of 0 to 3.
2. The polyimide precursor of claim 1 , wherein in Formula 1,
R 1 and R 2 are each independently halogen, (C 1 -C 10 )alkyl or halo(C 1 -C 10 )alkyl; and
n and m are each independently an integer of 0 to 1.
3. The polyimide precursor of claim 1 , wherein the Formula 1 is represented by the following Formula 2:
R 1 and R 2 are each independently halogen, (C 1 -C 10 ) alkyl, halo(C 1 -C 10 )alkyl, (C 1 -C 10 )alkoxy, or (C 6 -C 12 ) aryl; and
m and n are each independently an integer of 0 to 3.
4. The polyimide precursor of claim 3 , wherein in Formula 2, R 1 and R 2 are each independently halogen, (C 1 -C 5 )alkyl or halo(C 1 -C 5 )alkyl; and n and m are each independently an integer of 0 to 1.
5. The polyimide precursor of claim 1 , wherein the acid dianhydride compound is represented by the following Formula 3:
wherein
R 11 is (C 1 -C 10 ) alkyl or halo(C 1 -C 10 )alkyl; and
p is an integer of 0 to 2.
6. The polyimide precursor of claim 1 , further comprising a structural unit derived from a diamine compound represented by the following Formula 4:
wherein
R 3 and R 4 are each independently halogen, (C 1 -C 10 ) alkyl, halo(C 1 -C 10 )alkyl, (C 1 -C 10 )alkoxy, or (C 6 -C 12 ) aryl;
R 5 is hydrogen, (C 1 -C 10 ) alkyl, halo(C 1 -C 10 )alkyl, (C 1 -C 10 )alkoxy, or (C 6 -C 12 ) aryl; and
s and t are integers of 0 to 3.
7. The polyimide precursor of claim 1 , comprising a repeating unit represented by the following Formula 11:
wherein
A is O or S;
R 1 and R 2 are each independently halogen, (C 1 -C 10 ) alkyl, halo(C 1 -C 10 )alkyl, (C 1 -C 10 )alkoxy, or (C 6 -C 12 ) aryl;
R 11 is (C 1 -C 10 ) alkyl or halo(C 1 -C 10 )alkyl;
R a and R b are each independently hydrogen or (C 1 -C 10 )alkyl;
m and n are each independently an integer of 0 to 3; and
p is an integer of 0 to 2.
8. The polyimide precursor of claim 7 , wherein the polyimide precursor comprises 10 to 100 mol % of the repeating unit represented by Formula 11.
9. A polyimide precursor solution comprising the polyimide precursor of claim 1 and a solvent.
10. The polyimide precursor solution of claim 9 , wherein the solvent is selected from amides.
11. The polyimide precursor solution of claim 10 , wherein the amides are N,N-diethylacetamide, N,N-diethylformamide, N-ethylpyrrolidone, N,N-dimethylpropionamide, N,N-diethylpropionamide, or a mixture thereof.
12. A polyimide film comprising a repeating unit represented by the following Formula 12:
A is O or S;
R 1 and R 2 are each independently halogen, (C 1 -C 10 ) alkyl, halo(C 1 -C 10 )alkyl, (C 1 -C 10 )alkoxy, or (C 6 -C 12 ) aryl;
R 11 is (C 1 -C 10 ) alkyl or halo(C 1 -C 10 )alkyl;
m and n are each independently an integer of 0 to 2; and
p is an integer of 0 to 2.
13. The polyimide film of claim 12 , further comprising a repeating unit represented by the following Formula 13:
wherein
R 3 and R 4 are each independently halogen, (C 1 -C 10 ) alkyl, halo(C 1 -C 10 )alkyl, (C 1 -C 10 )alkoxy, or (C 6 -C 12 ) aryl;
R 5 is hydrogen, (C 1 -C 10 ) alkyl, halo(C 1 -C 10 )alkyl, (C 1 -C 10 )alkoxy, or (C 6 -C 12 ) aryl;
R 11 is (C 1 -C 10 ) alkyl or halo(C 1 -C 10 )alkyl;
s and t are integers of 0 to 3; and
p is an integer of 0 to 2.
14. The polyimide film of claim 12 , wherein the polyimide film has a coefficient of thermal expansion of more than 0 to 20 ppm/° C. at 100 to 450° C.
15. The polyimide film of claim 12 , wherein the polyimide film has a YI of less than 25 as measured according to ASTM E313, and a Young's modulus of more than 6.0 as measured according to ASTM D882.
16. The polyimide film of claim 12 , wherein the polyimide film is used for a substrate for an element, a substrate for a display, an optical film, an integrated circuit (IC) package, an adhesive film, a multilayer flexible printed circuit (FRC), a tape, a touch panel, or a protective film for an optical disk.
17. A photoelectric element comprising the polyimide film of claim 12 .