Composition for preparing polyimide-inorganic particle composite, article prepared therefrom, and optical device comprising same

Patent metadata

Field	Value
Publication number	US-10059805-B2
Application number	US-201514873376-A
Country	US
Kind code	B2
Filing date	Oct 2, 2015
Priority date	Oct 2, 2014
Publication date	Aug 28, 2018
Grant date	Aug 28, 2018

Abstract

A composition for preparing a polyimide-inorganic particle composite, including a tetracarboxylic acid dianhydride represented by Chemical Formula 1, a diamine represented by Chemical Formula 2, and an inorganic particle having an amino group on its surface:

wherein the definitions of groups R 1 and R 2 in Chemical Formula 1 and Chemical Formula 2 are the same as described in the detailed description.

First claim

What is claimed is:

1. A film comprising polyimide-inorganic particle composite prepared by a reaction among:
a tetracarboxylic acid dianhydride represented by Chemical Formula 1,
a diamine represented by Chemical Formula 2, and
an inorganic particle comprising an amino group on its surface:

wherein in Chemical Formula 1 and Chemical Formula 2,
R 1 and R 2 are the same or different, and are each independently a C4 to C30 alicyclic organic group, or a substituted or unsubstituted C6 to C30 aromatic organic group, wherein the alicyclic or aromatic organic group comprises alicyclic or aromatic one ring, two or more alicyclic or aromatic rings fused together to provide a condensed ring system, or two or more rings 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(C n H 2n+1 ) 2 —, —C(C n F 2n+1 ) 2 —, wherein 1≤n≤10, —C(═O)NH—, a C3 to C10 cycloalkylene group, a C2 to C10 heterocycloalkylene group, a C6 to C15 arylene group, and a C3 to C15 heteroarylene group,
wherein the substituted C6 to C30 aromatic organic group is substituted with at least one substituent selected from halogen, a hydroxyl group, nitro group, cyano group, an amino group (—NH 2 , —NH(R 100 ) or —N(R 101 )(R 102 ), wherein R 100 , R 101 , and R 102 are the same or different, and are each independently a C1 to C10 alkyl group, an amidino group, a hydrazine group, a hydrazone group, a carboxyl group, or a substituted or unsubstituted alkyl group, where the substitution is substituted with at least one halogen,
wherein the inorganic particle is an oxide of at least one element selected from Ti, Al, Zr, Sn, B, Ce, Sr, Ca, Ba, In, and W, or a graphene oxide,
wherein the inorganic particle has an average size of from about 0.1 nanometers to about 200 nanometers,
wherein the amino group on the surface of the inorganic particle is reacted with the tetracarboxylic acid dianhydride represented by Chemical Formula 1 to form an imide, and
wherein an amount of the inorganic particle is less than or equal to about 2 percent by volume based on the total volume of a solid content of the polyimide.

2. The film according to claim 1 , wherein the tetracarboxylic acid dianhydride represented by Chemical Formula 1 comprises a tetracarboxylic acid dianhydride represented by Chemical Formula 1-1:

wherein in Chemical Formula 1-1,
R 10 is single bond, 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(C n H 2n+1 ) 2 —, —C(C n F 2n+1 ) 2 —, wherein 1≤n≤10, —C(═O)NH—, a C3 to C10 cycloalkylene group, a C2 to C10 heterocycloalkylene group, a C6 to C15 arylene group, or a C3 to C15 heteroarylene group,
R 11 and R 12 are the same or different and are independently a halogen, hydroxyl group, a C1 to C10 aliphatic organic group, a C6 to C20 aromatic organic group, a group of formula —OR 201 , wherein R 201 is a C1 to C10 aliphatic organic group, or a silyl group of formula —SiR 210 R 211 R 212 , wherein R 210 , R 211 , and R 212 are the same or different and are independently hydrogen or a C1 to C10 aliphatic organic group,
n1 and n2 are the same or different and are independently an integer ranging from 0 to 3.

3. The film according to claim 2 , wherein the tetracarboxylic acid dianhydride represented by Chemical Formula 1-1 is a combination of a tetracarboxylic dianhydride represented by Chemical Formula 1-2 and a tetracarboxylic dianhydride represented by Chemical Formula 1-3:

wherein in Chemical Formulae 1-2 and 1-3,
R 10 , R 11 , R 12 , n1, n2 are the same as defined in claim 2 .

4. The film according to claim 2 , wherein the tetracarboxylic acid dianhydride represented by Chemical Formula 1 further comprises a tetracarboxylic acid dianhydride represented by Chemical Formula 1-4:

5. The film according to claim 2 , wherein the tetracarboxylic acid dianhydride represented by Chemical Formula 1-1 is a combination of a tetracarboxylic dianhydride represented by Chemical Formula 1-5 and a tetracarboxylic dianhydride represented by Chemical Formula 1-6:

wherein in Chemical Formulae 1-5 and 1-6,
R 11 , R 12 , n1, n2 are the same as defined in claim 2 .

6. The film according to claim 1 , wherein the inorganic particle comprises two or more amino groups on its surface.

7. The film according to claim 1 ,
wherein a compound comprising an amino group end is attached to a surface of the inorganic particle.

8. The film according to claim 1 , wherein the inorganic particle is selected from Al 2 O 3 , TiO 2 , ZrO 2 , Indium Tin Oxide, SrCO 3 , ZrW 2 O 8 , antimony doped tin oxide, and graphene oxide.

9. The film according to claim 7 , wherein the compound comprising an amino group end is represented by Chemical Formula 3:

wherein in Chemical Formula 3,
R a is a C1 to C20 alkylene, a C2 to C20 alkenylene, a C2 to C20 alkynylene, a C3 to C20 cycloalkylene, a C3 to C20 cycloalkenylene, a C3 to C20 cycloalkynylene, a C6 to C18 arylene, or a C6 to C19 aralkylene,
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 the substituent is selected from an acryloxy group, a glycidoxy group, or an isocyanato group,
R c is hydrogen, a C1 to C20 alkyl, a C2 to C20 alkenyl, a C2 to C20 alkynyl, a C3 to C20 cycloalkyl, or a C6 to C18 aryl, and
n is an integer ranging from 1 to 3.

10. The film according to claim 9 , wherein the compound represented by Chemical Formula 3 is selected from 3-aminopropyl trimethoxysilane 3-aminopropyl triethoxysilane, or 3-aminophenyl trimethoxysilane.

11. The film according to claim 1 , wherein the tetracarboxylic acid dianhydride represented by Chemical Formula 1 is one or more selected from 2,3,3′,4′-biphenyltetracarboxylic dianhydride, 2,3,3′,4′-diphenylsulfone tetracarboxylic dianhydride, 3,4′-oxydiphthalic anhydride, 3,3′,4,4′-biphenyl tetracarboxylic dianhydride, bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride, 3,3′,4,4′-diphenylsulfone tetracarboxylic dianhydride, 4,4′-(hexafluoroisopropylidene)diphthalic anhydride, 4,4′-oxydiphthalic anhydride, pyromellitic dianhydride, and 4-(2,5-dioxotetrahydrofuran-3-yl)-1,2,3,4-tetrahydronaphthalene-1,2-dicarboxylic anhydride.

12. The film according to claim 1 , wherein the diamine represented by Chemical Formula 2 is one or more selected from the following chemical formulae:

wherein in the chemical formulae,
R 32 to R 52 are the same or different and are each independently a halogen, a nitro group, a

Assignees

• Samsung Electronics Co Ltd

Inventors

• Jee Sang Soo
• Kang Young Jae
• Jeon Hyun Jeong
• Sohn Byung Hee

Classifications

• C08G73/106 Primary

  containing silicon · CPC title

• C08G73/1039

  comprising halogen-containing substituents · CPC title

• C08G73/1042

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

• C08L79/08

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

• C09J179/08

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