Tetracarboxylic acid dianhydride and method for preparing the same
View Patent ↗Provided are a novel tetracarboxylic acid dianhydride and a method for preparing the same. According to an exemplary embodiment of the present invention, a novel tetracarboxylic acid dianhydride appropriate for providing a polyimide film having high transparency and thermal resistance and having excellent thermal dimensional stability due to a substrate of which the stress is not increased even with a heat treatment at a high temperature and a method for preparing the same may be provided.
1. A tetracarboxylic acid dianhydride represented by the following Chemical Formula 1:
wherein
Q 1 is a single bond, —C(═O)—, —C(═O)O—, —C(═O)NH—, —NR′—, —S—, —SO 2 —, —CH 2 —, or a combination thereof, wherein R′ is hydrogen or C1-C10 alkyl;
R 1 and R 2 are independently of each other a halogen, hydroxy, thiol, nitro, cyano, C1-C10 alkyl, C1-C10 alkoxy, C6-C20 aryl, or a combination thereof, or may be connected to an adjacent substituent to form a ring; and
n and m are independently of each other an integer selected from 0 to 4, and when n and m are an integer of 2 or more, R 1 and R 2 may be the same as or different from each other.
2. The tetracarboxylic acid dianhydride of claim 1 , wherein the tetracarboxylic acid dianhydride is a compound represented by the following Chemical Formula 2:
wherein
R 1 , R 2 , n, and m are as defined in Chemical Formula 1 of claim 1 .
3. The tetracarboxylic acid dianhydride of claim 1 , wherein the tetracarboxylic acid dianhydride is selected from compounds represented by the following Chemical Formulae 3 to 5:
wherein
R 1 , R 2 , R′, n, and m are as defined in Chemical Formula 1 of claim 1 .
4. The tetracarboxylic acid dianhydride of claim 1 , wherein in Chemical Formula 1, R 1 and R 2 are independently of each other a halogen, hydroxy, thiol, nitro, cyano, C1-C10 alkyl, C1-C10 alkoxy, C6-C20 aryl, C1-C10 haloalkyl, or C1-C10 haloalkoxy, and n and m are independently of each other an integer selected from 0 to 2.
5. The tetracarboxylic acid dianhydride of claim 1 , wherein in Chemical Formula 1, R 1 and R 2 are independently of each other a halogen, hydroxy, thiol, nitro, cyano, C1-C4 alkyl, C1-C4 alkoxy, C6-C18 aryl, C1-C4 haloalkyl, or C1-C4 haloalkoxy, and n and m are independently of each other an integer selected from 0 to 2.
6. The tetracarboxylic acid dianhydride of claim 1 , wherein in Chemical Formula 1, R 1 and R 2 are independently of each other a halogen, nitro, cyano, C1-C4 alkyl, C1-C4 alkoxy, C6-C12 aryl, C1-C4 haloalkyl, or C1-C4 haloalkoxy, and n and m are independently of each other an integer selected from 0 to 2 and satisfy 0≤n+m≤2.
7. The tetracarboxylic acid dianhydride of claim 1 , wherein the tetracarboxylic acid dianhydride are at least one compound selected from the following structures:
8. A method for preparing a tetracarboxylic acid dianhydride represented by the following Chemical Formula 1, the method comprising: dehydrating and cyclizing a compound represented by the following Chemical Formula A in the presence of a dehydrating agent:
wherein
Q 1 is a single bond, —C(═O)—, —C(═O)O—, —C(═O)NH—, —NR′—, —S—, —SO 2 —, —CH 2 —, or a combination thereof, wherein R′ is hydrogen or C1-C10 alkyl;
R 1 and R 2 are independently of each other a halogen, hydroxy, thiol, nitro, cyano, C1-C10 alkyl, C1-C10 alkoxy, C6-C20 aryl, or a combination thereof, or may be connected to an adjacent substituent to form a ring; and
n and m are independently of each other an integer selected from 0 to 4, and when n and m are an integer of 2 or more, R 1 and R 2 may be the same as or different from each other.
9. The method for preparing a tetracarboxylic acid dianhydride of claim 8 , wherein the dehydrating agent is an acid anhydride.
10. A composition comprising the tetracarboxylic acid dianhydride of claim 1 .
11. The composition of claim 10 , further comprising: an organic solvent.
12. The composition of claim 11 , wherein the tetracarboxylic acid dianhydride is comprised at 1 to 30 wt %, based on a total weight.