Diamine, polymer and film produced using the same
The present invention relates to a diamine, and a polymer and film produced using the same. Specifically, the diamine may be significantly effectively used as a monomer for producing a polyimide-based film that is colorless and transparent and has improved mechanical strength.
1. A diamine represented by the following Chemical Formula 1:
where in Chemical Formula 1,
R 1 and R 2 are each independently (C2-C20) alkyl, (C1-C20) alkoxy, halo (C1-C20) alkyl, (C1-C20) alkylcarbonyl, (C1-C20) alkoxycarbonyl, (C6-C20) arylcarbonyl, tri(C1-C20) alkylsilyl, carboxyl, hydroxy, amino, nitro, cyano, or halogen;
R 3 is (C1-C20) alkyl, (C1-C20) alkoxy, halo (C1-C20) alkyl, (C1-C20) alkylcarbonyl, (C1-C20) alkoxycarbonyl, (C6-C20) arylcarbonyl, tri(C1-C20) alkylsilyl, carboxyl, hydroxy, amino, nitro, cyano, or halogen;
R a is hydrogen, (C1-C20) alkyl, or (C6-C20) aryl;
a and b are each independently an integer of 1 to 4;
c is an integer of 0 to 4;
when a, b, and c are integers of 2 or more, R 1 , R 2 , and R 3 may be the same as or different from each other; and
p is an integer of 1 to 3.
2. The diamine of claim 1 , wherein the diamine represented by Chemical Formula 1 is represented by the following Chemical Formula 2 or 3:
where in Chemical Formulas 2 and 3,
R 1 and R 2 are each independently (C2-C7) alkyl, (C1-C7) alkoxy, halo (C1-C7) alkyl, (C1-C7) alkylcarbonyl, (C1-C7) alkoxycarbonyl, (C6-C12) arylcarbonyl, tri(C1-C7) alkylsilyl, carboxyl, hydroxy, amino, nitro, cyano, or halogen;
R 3 and R 4 are each independently (C1-C7) alkyl, (C1-C7) alkoxy, halo (C1-C7) alkyl, (C1-C7) alkylcarbonyl, (C1-C7) alkoxycarbonyl, (C6-C12) arylcarbonyl, tri(C1-C7) alkylsilyl, carboxyl, hydroxy, amino, nitro, cyano, or halogen;
R a and R b are each independently hydrogen, (C1-C7) alkyl, or (C6-C12) aryl;
a and b are each independently an integer of 1 to 3;
c and d are each independently an integer of 0 to 3; and
when a, b, c, and d are integers of 2 or more, R 1 , R 2 , R 3 , and R 4 may be the same as or different from each other.
3. The diamine of claim 1 , wherein the diamine represented by Chemical Formula 1 is represented by the following Chemical Formula 4 or 5:
where in Chemical Formulas 4 and 5,
R 3 and R 4 are each independently (C1-C7) alkyl, (C1-C7) alkoxy, halo (C1-C7) alkyl, carboxyl, hydroxy, amino, or halogen;
R 11 and R 12 are each independently (C2-C7) alkyl, halo (C1-C7) alkyl, or halogen;
n and m are each independently an integer of 1 to 5;
x, y, c, and d are each independently an integer of 0 to 2; and
when x, y, c, and d are 2, R 11 , R 12 , R 3 , and R 4 may be the same as or different from each other.
4. The diamine of claim 1 , wherein the diamine represented by Chemical Formula 1 is represented by the following Chemical Formula 6 or 7:
where in Chemical Formulas 6 and 7,
R 3 and R 4 are each independently (C1-C5) alkyl, (C1-C5) alkoxy, halo (C1-C5) alkyl, carboxyl, hydroxy, amino, or halogen;
R 11 and R 12 are each independently (C2-C5) alkyl, halo (C1-C5) alkyl, or halogen;
x, y, and d are each independently 0 or 1;
c is an integer of 0 to 2; and
when c are 2, R 3 may be the same as or different from each other.
5. The diamine of claim 4 , wherein the diamine is selected from the following compounds:
6. A method of preparing a diamine, the method comprising preparing a diamine represented by the following Chemical Formula 1 by reducing a compound represented by the following Chemical Formula A under a reduction catalyst:
where in Chemical Formulas 1 and A,
Y 1 is nitro or amino; and
the definitions of R 1 to R 3 , R a , a, b, c, and p are the same as those in Chemical Formula 1 of claim 1 .
7. The method of claim 6 , wherein the reduction catalyst is selected from Zn, Cu, Ag, Au, Cd, Hg, Fe, K 4 [Fe(CN) 6 ], NaBH 4 , and a combination thereof.
8. The method of claim 7 , wherein the reduction catalyst further comprises a cocatalyst selected from NH 4 Cl, H 2 CO 3 , H 3 PO 4 , HCl, CH 3 COOH, and a combination thereof.
9. The method of claim 6 , wherein the compound represented by Chemical Formula A is prepared by reacting Y 2 of a compound represented by the following Chemical Formula A-1 with X of a compound represented by the following Chemical Formula A-2:
where in Chemical Formulas A, A-1, and A-2,
X is halogen;
Y 1 is nitro or amino;
Y 2 is
R 1 and R 2 are each independently (C2-C20) alkyl, (C1-C20) alkoxy, halo (C1-C20) alkyl, (C1-C20) alkylcarbonyl, (C1-C20) alkoxycarbonyl, (C6-C20) arylcarbonyl, tri(C1-C20) alkylsilyl, carboxyl, hydroxy, amino, nitro, cyano, or halogen;
R 3 is (C1-C20) alkyl, (C1-C20) alkoxy, halo (C1-C20) alkyl, (C1-C20) alkylcarbonyl, (C1-C20) alkoxycarbonyl, (C6-C20) arylcarbonyl, tri(C1-C20) alkylsilyl, carboxyl, hydroxy, amino, nitro, cyano, or halogen;
R a is hydrogen, (C1-C20) alkyl, or (C6-C20) aryl;
a and b are each independently an integer of 1 to 4;
c is an integer of 0 to 4;
when a, b, and c are integers of 2 or more, R 1 , R 2 , and R 3 may be the same as or different from each other; and
p is an integer of 1 to 3.
10. A polymer comprising a unit derived from the diamine of claim 1 ; and a unit derived from a dianhydride, a unit derived from an aromatic diacid dichloride, or a combination thereof.
11. The polymer of claim 10 , wherein the dianhydride comprises an aromatic dianhydride, an alicyclic dianhydride, or a combination thereof.
12. The polymer of claim 10 , wherein the dianhydride comprises a fluorine-based aromatic dianhydride and an alicyclic dianhydride.
13. The polymer of claim 10 , wherein the aromatic diacid dichloride comprises terephthaloyl dichloride, isophthaloyl dichloride, 1,1′-biphenyl-4,4′-dicarbonyl dichloride, 1,4-naphthalenedicarboxylic dichloride, 2,6-naphthalenedicarboxylic dichloride, 1,5-naphthalenedicarboxylic dichloride, 4,4′-oxybis(benzoyl chloride), or a combination thereof.
14. A composition for forming a film, comprising the polymer of claim 10 .
15. A film produced using the composition for forming a film of claim 14 .
16. The film of claim 15 , wherein the film comprises polyimide, polyamide, or a combination thereof.
17. The film of claim 16 , wherein a thickness of the film is 1 to 500 um.
18. The film of claim 17 , wherein the film has a yellow index (YI) of 10 or less when measured according to ASTM E313, a haze of 2.0% or less when measured according to ASTM D1003, and a total light transmittance of 80% or more when measured according to ASTM D1003.
19. The film of claim 17 , wherein the film has a modulus of 5 GPa or more when measured according to ASTM D882.
20. A multi-layer structure comprising the film of claim 15 .
21. A display device comprising the film of claim 15 .