Polyimide-based film having excellent surface evenness and method for producing same

Patent metadata

Field	Value
Publication number	US-12486369-B2
Application number	US-202017760759-A
Country	US
Kind code	B2
Filing date	Sep 14, 2020
Priority date	Sep 27, 2019
Publication date	Dec 2, 2025
Grant date	Dec 2, 2025

Abstract

Disclosed are a polyimide-based film and a method of producing the same, and more particularly, a polyimide-based film having excellent surface evenness and suppressed waviness due to low Kc of 1.55 or less and a method of producing the same.

First claim

The invention claimed is:

1 . A polyimide-based film having a Kc value of 1.55 or less,
wherein the polyimide-based film is produced by:
preparing a liquid resin composition using monomer components including dianhydride and diamine,
producing a gel-state film using the liquid resin composition,
first drying the gel-state film at a temperature of 50 to 150° C. at a wind speed of 0 m/s or less for a drying period of 2 to 20 minutes, and
second drying the gel-state film at a wind speed of 1.0 to 5.0 m/s at 70 to 140° C. after the first drying,
wherein the Kc value is a curvature parameter measured for a waviness having a wavelength range of 1.0 to 3.0 mm by phase stepped deflectometry, wherein a polyimide-based film sample having a width of 15 cm×a length of 15 cm×thickness of 80 μm is used for measuring K, and a measuring device is in a curvature mode K with 1.0 to 3.0 mm wavelength range, and a sheet of black matte paper is placed on a surface plate in a dark room, the sample to be measured is placed thereon, the Kc value is measured 10 times, and the average value is used as the Kc value of the sample, wherein the polyimide-based film is produced from monomer components including dianhydride and diamine, the dianhydride comprises at least one selected from 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride, 3,3′,4,4′-biphenyl tetracarboxylic dianhydride, 4-(2,5-dioxotetrahydrofuran-3-yl)-1,2,3,4-tetrahydronaphthalene-1,2-dicarboxylic anhydride, pyromellitic dianhydride, 3,3′,4,4′-benzophenone tetracarboxylic dianhydride, 4,4′-oxydiphthalic anhydride, 4,4′-(3,4-bisdicarboxyphenoxy-diphenyl sulfide dianhydride, 3,3′,4,4′-diphenylsulfonetetracarboxylic dianhydride, 4,4′-(4,4′-Isopropylidenediphenoxy)bis(phthalic anhydride), cyclobutane-1,2,3,4-tetracarboxylic dianhydride, 1,2,3,4-cyclopentane-tetracarboxylic dianhydride, 1,2,4,5-cyclohexanetetracarboxylic dianhydride, and dicyclohexyl-3,4,3′,4′-tetracarboxylic dianhydride, the diamine comprises at least one selected from 3,4-oxydianiline, 4,4′-oxydianiline, p-phenylenediamine, m-phenylenediamine, 4,4-methylenedianiline, 3,3-methylenedianiline, 1,3-Bis(3-aminophenoxy)benzene, 1,3-Bis(4-aminophenoxy)benzene, 2,2′-bis[4-(4-aminophenoxy) phenyl] hexafluoropropane, 2,2′-bis(3-aminophenyl)hexafluoropropane, 2,2′-bis(4-aminophenyl) hexafluoropropane, bis(4-aminophenyl)sulfone, bis(3-aminophenyl)sulfone, 2,2′-bis(trifluoromethyl)benzidine, 1,3-cyclohexanediamine, 1,4-cyclohexanediamine, 2,2-bis[4-(4-aminophenoxy)phenyl]propane, 2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane, bis[4-(4-aminophenoxy)phenyl] sulfone, bis[4-(3-aminophenoxy)phenyl] sulfone, 9,9-bis(4-aminophenyl)fluorene and 9,9-bis(4-amino-3-fluorophenyl)fluorene.

2 . The polyimide-based film according to claim 1 , wherein the polyimide-based film has a Kc value of 1.45 or less.

3 . The polyimide-based film according to claim 1 , wherein the polyimide-based film has a Kc value of 1.10 to 1.45.

4 . The polyimide-based film according to claim 1 , wherein the monomer components further comprise a dicarbonyl compound.

5 . The polyimide-based film according to claim 4 , wherein the dicarbonyl compound comprises at least one of an aromatic dicarbonyl compound and an aliphatic dicarbonyl compound.

6 . The polyimide-based film according to claim 5 , wherein the aromatic dicarbonyl compound is represented by the following Formula 1:

wherein R 1 represents a single bond, *—Ar—*, *—O—Ar—*, *-CAL-*, or *—O-CAL-*;
X 1 and X 2 each independently represent hydrogen, a hydroxy group (OH) or a halogen element; and
X 3 represents hydrogen or a halogen element,
wherein “Ar” represents a substituted or unsubstituted arylene group, and “CAL” represents a divalent cycloaliphatic group.

7 . The polyimide-based film according to claim 5 , wherein the aromatic dicarbonyl compound comprises at least one of a compound represented by the following Formula 3, a compound represented by the following Formula 4, a compound represented by the following Formula 5, a compound represented by the following Formula 6, a compound represented by the following Formula 7, a compound represented by the following Formula 8 and a compound represented by the following Formula 9:

8 . The polyimide-based film according to claim 5 , wherein the aliphatic dicarbonyl compound comprises at least one of a compound represented by the following Formula 10, a compound represented by the following Formula 11, a compound represented by the following Formula 12, and a compound represented by the following Formula 13:

9 . The polyimide-based film according to claim 1 , wherein, based on a thickness of 80 μm, the polyimide-based film has a haze of 2.0 or less, an average optical transmittance of 87% or more at a wavelength of 380 to 780 nm, and a yellow index of 5 or less.

10 . A method of producing a polyimide-based film comprising:
preparing a liquid resin composition using monomer components including dianhydride and diamine; producing a gel-state film using the liquid resin composition; first drying the gel-state film at a temperature of 50 to 150° C. at a wind speed of 1.0 m/s or less for a drying period of 2 to 20 minutes; and second drying the gel-state film at a wind speed of 1.0 to 5.0 m/s at 70 to 140° C. after the first drying, wherein, in the first drying, the drying coefficient conditions according to the following Equations 1 and 2 are satisfied when the temperature is A° C., the wind speed is B m/s and the drying period is T minutes:
0.5≤[( A− 40)× B×T ]/100≤10  [Equation 1]

2≤[( A− 40)× T ]/100≤10.  [Equation 2]

11 . The method according to claim 10 , wherein the monomer components further comprise a dicarbonyl compound.

12 . The method according to claim 10 , wherein the liquid resin composition has a viscosity of 1,000 to 250,000 cPs.

13 . The method according to claim 10 , wherein the wind speed in the first drying is 0.2 m/s or more.

14 . The method according to claim 10 , further comprising first heat-treating the gel-state film for 1 minute to 1 hour at a temperature of 100 to 500° C. after the second drying.

15 . The method according to claim 10 , wherein the production of the gel-state film comprises casting the liquid resin composition on a support.

16 . The method according to claim 10 , wherein the preparation of the liquid resin composition comprises:
reacting the monomer components in the presence of a first solvent to prepare a first polymer solution; adding a second solvent to the first polymer solution, followed by filtering and drying, to prepare a polymer solid; and dissolving the polymer solid in a third solvent.

Assignees

• Kolon Inc

Inventors

• Park Hyo Jun
• Yang Jong Won

Classifications

• C08J2379/08

  Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors · CPC title

• C08G73/1078

  wholly aromatic in the diamino moiety · CPC title

• C08G73/1007

  from tetracarboxylic acids or derivatives and diamines · CPC title

• C08J7/08

  Heat treatment · CPC title

• C08G73/1042

  Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds · CPC title