Composition for preparing polyimide-inorganic composite material, and article prepared by using same

Patent metadata

Field	Value
Publication number	US-10316155-B2
Application number	US-201514625348-A
Country	US
Kind code	B2
Filing date	Feb 18, 2015
Priority date	Jun 16, 2014
Publication date	Jun 11, 2019
Grant date	Jun 11, 2019

Abstract

A composition for preparing a polyimide-inorganic composite material including: a polyamic acid represented by Chemical Formula 1, a polyimide represented by Chemical Formula 2, or a combination thereof; an inorganic particle precursor; and water, wherein the polyamic acid, the polyimide, or the combination thereof is a reaction product of a dicarboxylic acid anhydride and a diamine, wherein the mole ratio of the diamine to the dicarboxylic acid anhydride is greater than 0.93 and less than 0.95, and wherein the inorganic particle precursor is included in an amount to provide an inorganic particle in an amount of greater than or equal to about 30 weight % and less than or equal to about 60 weight % based the total weight of the polyimide-inorganic composite material prepared:

wherein in Chemical Formulae 1 and 2, groups and variable are the same as defined in the specification.

First claim

What is claimed is:

1. A composition for preparing a polyimide-inorganic composite material comprising:
a polyamic acid represented by Chemical Formula 1, a polyimide represented by Chemical Formula 2, or a combination thereof;
an inorganic particle precursor; and
water,
wherein the polyamic acid, the polyimide, or the combination thereof is a reaction product of a dicarboxylic acid anhydride and a diamine,
wherein a mole ratio of the diamine to the dicarboxylic acid anhydride is greater than 0.93 and less than 0.95, and
wherein the inorganic particle precursor is included in an amount to provide an inorganic particle in an amount of greater than or equal to about 30 percent by weight and less than or equal to about 60 percent by weight based the total weight of the polyimide-inorganic composite material:

wherein in Chemical Formulae 1 and 2,
all Ar groups are represented by Chemical Formula 3, or
a part of Ar groups are represented by Chemical Formula 3, and the other Ar groups are represented by Chemical Formula 9:

wherein in Chemical Formula 3,
R 10 is a single bond, a substituted or unsubstituted C1 to C30 aliphatic organic group, a substituted or unsubstituted C3 to C30 alicyclic organic group, a substituted or unsubstituted C6 to C30 aromatic organic group, or a substituted or unsubstituted C2 to C30 heterocyclic organic group,
R 12 and R 13 are the same or different and each are independently a halogen, a hydroxyl group, a substituted or unsubstituted C1 to C10 aliphatic organic group, a substituted or unsubstituted C6 to C20 aromatic organic group, an alkoxy group of formula —OR 205 , wherein R 205 is a substituted or unsubstituted C1 to C10 aliphatic organic group, or a silyl group of formula —SiR 209 R 210 R 211 , wherein R 209 , R 210 , and R 211 are the same or different and each are independently a hydrogen, or a substituted or unsubstituted C1 to C10 aliphatic organic group, and
n7 and n8 are the same or different and each are independently an integer ranging from 0 to 3;
wherein in Chemical Formulae 1 and 2,
Ar′ is the same or different in each structure unit, and is represented by any one of Chemical Formulae 4 to 6:

wherein in Chemical Formula 4,
R 11 is a substituted or unsubstituted C3 to C30 alicyclic organic group, a substituted or unsubstituted C6 to C30 aromatic organic group, or a substituted or unsubstituted C2 to C30 heterocyclic organic group,
R 3 and R 4 are the same or different and each are independently a halogen, a hydroxyl group, a substituted or unsubstituted C1 to C10 aliphatic organic group, a substituted or unsubstituted C6 to C20 aromatic organic group, an alkoxy group of formula —OR 200 , wherein R 200 is a substituted or unsubstituted C1 to C10 aliphatic organic group, or a silyl group of formula —SiR 201 R 202 R 203 , wherein R 201 , R 202 , and R 203 are the same or different and each are independently a hydrogen, or a substituted or unsubstituted C1 to C10 aliphatic organic group, and
n1 and n2 are the same or different and each are independently an integer ranging from 0 to 4;

wherein in Chemical Formula 5,
R 6 and R 7 are the same or different and each are independently an electron withdrawing group,
R 8 and R 9 are the same or different, and each are independently a halogen, a hydroxy group, a substituted or unsubstituted C1 to C10 aliphatic organic group, a substituted or unsubstituted C6 to C20 aromatic organic group, an alkoxy group of formula —OR 204 , wherein R 204 is a substituted or unsubstituted C1 to C10 aliphatic organic group, or a silyl group of formula —SiR 205 R 206 R 207 , wherein R 205 , R 206 , and R 207 are the same or different, and each are independently a hydrogen, a substituted or unsubstituted C1 to C10 aliphatic organic group,
n3 is an integer ranging from 1 to 4,
n5 is an integer ranging from 0 to 3,
provided that n3+n5 is an integer ranging from 1 to 4,
n4 is an integer ranging from 1 to 4, and
n6 is an integer ranging from 0 to 3,
provided that n4+n6 is an integer ranging from 1 to 4;

wherein in Chemical Formula 6,
R 14 is O, S, C(═O), CH(OH), S(═O) 2 , Si(CH 3 ) 2 , (CH 2 ) p wherein 1≤p ≤10, (CF 2 ) q wherein 1≤q≤10, C(CH 3 ) 2 , C(CF 3 ) 2 , C(═O)NH, or a substituted or unsubstituted C6 to C30 aromatic organic group, wherein the aromatic organic group comprises one aromatic ring, two or more aromatic rings fused together to provide a condensed ring system, or two or more moieties linked through a single bond or through a functional group selected from a fluorenylene group, O, S, C(═O), CH(OH), S(═O) 2 , Si(CH 3 ) 2 , (CH 2 ) p wherein 1≤p≤10, (CF 2 ) q wherein 1≤q≤10, C(CH 3 ) 2 , C(CF 3 ) 2 , and C(═O)NH,
R 16 and R 17 are the same or different, and each are independently a halogen, a hydroxy group, a substituted or unsubstituted C1 to C10 aliphatic organic group, a substituted or unsubstituted C6 to C20 aromatic organic group, an alkoxy group of formula —OR 212 , wherein R 212 is a substituted or unsubstituted C1 to C10 aliphatic organic group, or a silyl group of formula —SiR 213 R 214 R 215 , wherein R 213 , R 214 , and R 215 are the same or different, and each are independently a hydrogen or a substituted or unsubstituted C1 to C10 aliphatic organic group, and
n9 and n10 are each independently an integer ranging from 0 to 4,
wherein in Chemical Formulae 1 and 2,
R a is a substituted or unsubstituted C1-C30 alkylene, a substituted or unsubstituted C2-C30 alkenylene, a substituted or unsubstituted C2-C30 alkynylene, a substituted or unsubstituted C3-C30 cycloalkylene, a substituted or unsubstituted C3-C30 cycloalkenylene, a substituted or unsubstituted C8-C30 cycloalkynylene, a substituted or unsubstituted C6-C30 arylene, or a substituted or unsubstituted C7-C30 arylalkylene,
R b is hydrogen, a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C2 to C20 alkenyl, a substituted or unsubstituted C2 to C20 alkynyl, a substituted or unsubstituted C3 to C20 cycloalkyl, or a substituted or unsubstituted C6 to C18 aryl,
wherein each of R a and R b are substituted with an acryloxy group, glycidoxy group, or a isocyanato group,
R c is hydrogen, a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C2 to C20 alkenyl, a substituted or unsubstituted C2 to C20 alkynyl, a substituted or unsubstituted C3 to C20 cycloalkyl, or a substituted or unsubstituted C6 to C18 aryl,
n is an integer ranging from 1 to 3, and
x and y are independently an integer greater than or equal to 1.

2. The composition according to claim 1 , wherein the inorganic particle precursor is selected from an oxide or hydroxide of Ti, Si, Al, Zr, Sn, B, Ce, or a combination thereof.

3. The composition according to claim 1 , wherein the inorganic particle precursor is a precursor of SiO 2 or TiO 2 .

4. The composition according to claim 1 , wherein the inorganic precursor is selected from tetramethoxysilane, tetrae

Assignees

• Samsung Electronics Co Ltd
• Samsung Electronics Ltd

Inventors

• Cho Chung Kun
• Bae Woo-Jin
• Kalinina Fedosya
• Kovalev Mikhail

Classifications

• C08J5/18 Primary

  Manufacture of films or sheets · CPC title

• C08K3/36

  Silica · CPC title

• C08G73/1042

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

• C09D179/08

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

• C08L79/08

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