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US 2022/0033585 A1Published application
Diamine compound, and polyimide precursor and polyimide film using same
AssigneeLG Chem, Ltd.
InventorsKichul KOO, Kyunghwan KIM
Life of this patent
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Abstract
The present invention discloses a novel diamine that has a structure bearing an intramolecular imide group and additionally an amide-substituted aromatic ring group at opposite sides of the imide group. The use of the novel diamine as a polymerization ingredient in polyimide production can provide a polyimide film which has remarkably improved mechanical and thermal properties while maintaining optical properties.
Claims14
A diamine having a structure of the following formula 1:
- in the formula 1,
- Z1 to Z8 are each independently a carbon atom or a nitrogen atom, with the proviso that Z1 to Z8 are not nitrogen atoms at the same time, R1, R2, R3 and R4 are each independently selected from the group consisting of an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkenyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 18 carbon atoms, n1, n2, n3 and n4 are each independently an integer of 0 to 4, and X is a single bond or a functional group selected from the group consisting of O, S, S—S, C(═O), —C(═O)O—, CH(OH), S(═O)2, Si(CH3)2, CR′R″, C(═O)NH and a combination thereof, wherein R′ and R″ are each independently selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 10 carbon atoms and a fluoroalkyl group having 1 to 10 carbon atoms.
A method for preparing a diamine having a structure of the formula 1, the method comprising the steps of:
- reacting a compound of the formula (i) with a compound of the formula (ii) to obtain a compound of the formula (iii);
- reacting the compound of the formula (iii) with a compound of the formula (iv) to obtain a compound of the formula (v);
- and
- reducing the compound of the formula (v) to obtain the diamine of the formula 1:
- wherein,
- Za to Zd are each independently a carbon atom or a nitrogen atom, with the proviso that Za to Zd are not nitrogen atoms at the same time, R1, R2 and Ra are each independently selected from the group consisting of an alkyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an alkenyl group having 1 to 10 carbon atoms, and an aryl group having 6 to 18 carbon atoms, n1, n2 and n are each independently an integer of 0 to 4, and X is a single bond or a functional group selected from the group consisting of O, S, S—S, C(═O), —C(═O)O—, CH(OH), S(═O)2, Si(CH3)2, CR′R″, C(═O)NH and a combination thereof, wherein R′ and R″ are each independently selected from the group consisting of a hydrogen atom, an alkyl group having 1 to 10 carbon atoms and a fluoroalkyl group having 1 to 10 carbon atoms.
3 more elements
Dependencies are inferred from the claim text.