Dianhydride monomer having side chain, polyimide compound having side chain and manufacturing method thereof
AssigneeUnimicron Technology Corp.
InventorHAN-PEI HUANG
Life of this patent
Estimating the term…
Abstract
A dianhydride monomer having a large side chain R is provided. The large side chain would interrupt the symmetry and regularity of diamine monomer. The diamine monomer has the general formula shown as formula (I) below: The functional group R includes α-substitution cycloalkene having at least a tertiary carbon atom, cycloalkene having at least a tertiary carbon atom, cycloalkane having at least a tertiary carbon atom, α-substitution phenyl, phenyl, α-substitution naphthalyl, naphthalyl, α-substitution phenanthrenyl, phenanthrenyl, α-substitution anthracenyl, anthracenyl, α-substitution adamantyl, adamantyl, α-substitution adamantyl and adamantyl.
Claims18
A dianhydride monomer having side chain, comprising the formula is listed as formula (I) below:
- wherein R comprises aromatic hydrocarbon or alicyclic hydrocarbon.
A manufacturing method of dianhydride monomer having side chain, comprising:
- (A) heat refluxing the solution containing bromo compound (a), hydroquinone compound and benzene to separate out solid hydroquinone compound (b),
- wherein the reaction temperature is 80-85° C., and the reaction time is 3-4 days,
- wherein the formula of bromo compound (a) is shown as formula (II) below:
- wherein the general formula of hydroquinone compound (b) is shown as formula (III) below:
- (B) heating the solution containing hydroquinone compound (b), and utilizing the methanol solution as the precipitant to form bis(3,4-dicyanophenoxy) compound (c),
- wherein the reaction temperature is 75 to 80° C., and the reaction time is 6 to 12 hours,
- wherein the general formula of bis(3,4-dicyanophenoxy) compound (c) is shown as formula (V) below:
- and
- (C) heating refluxing the solution containing bis(3,4-dicyanophenoxy) compound (c), potassium hydroxide, and methanol to separate out the solid bis(3,4-dicarboxyphenoxy) compound (d),
- wherein the reaction temperature is 70 to 85° C., and the reaction time is 4 to 5 days,
- wherein the general formula of bis(3,4-dicarboxyphenoxy) compound (d) is shown as formula (VI) below:
- (D) dehydrated ring-closuring the solution containing bis(3,4-dicarboxyphenoxy) compound (d), acetic anhydride, and acetic acid anhydride to form the dianhydride monomer (e),
- wherein the reaction temperature is 130 to 140° C., and the reaction time is 1 to 6 days,
- wherein the general formula of dianhydride monomer (e) is shown as formula (I) below:
- wherein R group comprises aromatic hydrocarbon or alicyclic hydrocarbon.
A polyimide compound having side chain, comprising the formula is shown as formula (VIII) below:
- wherein R group comprises aromatic hydrocarbon or alicyclic hydrocarbon,
- wherein R′ is selected from the group consisting of:
A manufacturing method of polyimide compound having side chain, comprising:
- (A) dissolving dianhydride monomer, diamine monomer into cresol by stirring under anhydrous condition to form polyamic acid compound solution,
- wherein the general formula of dianhydride monomer is shown as formula (I) below:
- wherein the general formula of diamine monomer is shown as formula (IX) below:
- H2N—R′—NH2 formula (IX),
- wherein the general formula of polyamic acid compound is shown as formula (X) below:
- wherein R comprises aromatic hydrocarbon or alicyclic hydrocarbon,
- wherein R′ is selected from the group consisting of:
- wherein the reaction temperature is 20 to 30° C., the reaction time is 6 to 7 hours;
- (B) adding 5-10 drops of isoquinoline to polyamic acid compound solution, and heating refluxing the solution to form polyimide compound solution,
- wherein the reaction temperature is 100 to 200° C., the reaction time is 8 to 12 hours;
- and
- (C) cooling polyimide compound solution and adding polyimide compound solution into ethanol to precipitate out solid polyimide compound,
- wherein the general formula of polyimide compound is shown as formula (VIII) below:
Dependencies are inferred from the claim text.