Transparent polymer film and electronic device including the same

Patent metadata

Field	Value
Publication number	US-9902814-B2
Application number	US-201615356952-A
Country	US
Kind code	B2
Filing date	Nov 21, 2016
Priority date	Nov 23, 2015
Publication date	Feb 27, 2018
Grant date	Feb 27, 2018

Abstract

A composition for preparing an organic/inorganic hybrid poly(amide-imide) copolymer including a poly(amide-imide) copolymer, a poly(amide-amic acid) copolymer, or a poly(amide-imide/amic acid) copolymer including a structural unit represented by Chemical Formula 1; and a structural unit represented by Chemical Formula 2, a structural unit represented by Chemical Formula 3, or a combination thereof, and a polyhedral oligomeric silsesquioxane including a functional group capable of forming a hydrogen bond:

wherein in Chemical Formulae 1 to 3, A, B, D, and E are the same as defined in the detailed description.

First claim

What is claimed is:

1. A composition for preparing an organic/inorganic hybrid poly(amide-imide) copolymer, the composition comprising:
a poly(amide-imide) copolymer, a poly(amide-amic acid) copolymer, or a poly(amide-imide/amic acid) copolymer comprising:
a structural unit represented by Chemical Formula 1; and a structural unit represented by Chemical Formula 2, a structural unit represented by Chemical Formula 3, or a combination thereof, and
a polyhedral oligomeric silsesquioxane comprising a functional group capable of forming a hydrogen bond:

wherein in Chemical Formula 1,
A and B are independently a substituted or unsubstituted divalent C6 to C24 aliphatic cyclic group, a substituted or unsubstituted C6 to C24 aromatic ring group or a substituted or unsubstituted divalent C4 to C24 hetero aromatic ring group, wherein the C6 to C24 aliphatic cyclic group, the C6 to C24 aromatic ring group, or the C4 to C24 hetero aromatic ring group is present as a single ring, two or more rings thereof are fused to each other to provide a condensed ring system, or two or more of the single ring or the condensed ring system are linked through a 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), —CR″R′″— (wherein R″ and R′″ are independently hydrogen, a C1 to C10 aliphatic hydrocarbon group, a C6 to C20 aromatic hydrocarbon group, or a C6 to C20 alicyclic hydrocarbon group), —C(CF 3 ) 2 —, —C(CF 3 )(C 6 H 5 )—, or —C(═O)NH—,

wherein in Chemical Formulae 2 and 3,
D is a substituted or unsubstituted tetravalent C6 to C24 aliphatic cyclic group, a substituted or unsubstituted C6 to C24 aromatic ring group, or a substituted or unsubstituted tetravalent C4 to C24 hetero aromatic ring group, wherein the C6 to C24 aliphatic cyclic group, the C6 to C24 aromatic ring group, or the C4 to C24 hetero aromatic ring group is present as a single ring, two or more rings thereof are fused to each other to provide a condensed ring system, or two or more of the single ring or the condensed ring system are linked through a single bond, —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), —CR″R′″— (wherein R″ and R′″ are independently hydrogen, a C1 to C10 aliphatic hydrocarbon group, a C6 to C20 aromatic hydrocarbon group, or a C6 to C20 alicyclic hydrocarbon group), —C(CF 3 )(C 6 H 5 )—, or —C(═O)NH—, and
E is a substituted or unsubstituted divalent C6 to C24 aliphatic cyclic group, a substituted or unsubstituted C6 to C24 aromatic ring group or a substituted or unsubstituted divalent C4 to C24 hetero aromatic ring group, wherein the C6 to C24 the aliphatic cyclic group, the C6 to C24 aromatic ring group, or the C4 to C24 hetero aromatic ring group is present as a single ring, two or more rings thereof are fused to each other to provide a condensed ring system, or two or more of the single ring or the condensed ring system are linked through a 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), —CR″R′″— (wherein R″ and R′″ are independently hydrogen, a C1 to C10 aliphatic hydrocarbon group, a C6 to C20 aromatic hydrocarbon group, or a C6 to C20 alicyclic hydrocarbon group), —C(CF 3 ) 2 —, —C(CF 3 )(C 6 H 5 )—, or —C(═O)NH—.

2. The composition for preparing an organic/inorganic hybrid poly(amide-imide) copolymer of claim 1 , wherein the functional group capable of forming a hydrogen bond of the polyhedral oligomeric silsesquioxane is —OH, —SH, —NH 2 , or a combination thereof.

3. The composition for preparing an organic/inorganic hybrid poly(amide-imide) copolymer of claim 1 , wherein the polyhedral oligomeric silsesquioxane including the functional group capable of forming a hydrogen bond is represented by Chemical Formula 4 or Chemical Formula 5:

wherein in Chemical Formulae 4 and 5,
R is independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a combination thereof, and
R′ is independently —OH, —SH, or —NH 2 .

4. The composition for preparing an organic/inorganic hybrid poly(amide-imide) copolymer of claim 3 , wherein
R of Chemical Formula 4 and 5 is independently a substituted or unsubstituted C1 to C12 alkyl group, a substituted or unsubstituted C3 to C10 cycloalkyl group, a substituted or unsubstituted C6 to C12 aryl group, or a combination thereof, and
R′ are each independently —OH, —SH, or —NH 2 .

5. The composition for preparing an organic/inorganic hybrid poly(amide-imide) copolymer of claim 3 , wherein
R of Chemical Formula 4 and 5 is independently a cyclohexyl group or phenyl group, and
each R′ is —OH.

6. The composition for preparing an organic/inorganic hybrid poly(amide-imide) copolymer of claim 1 , wherein
A of Chemical Formula 1 is selected from chemical formulae of Group 1:

wherein in the above chemical formulae,
R 18 to R 33 are the same or different and are independently a deuterium, a halogen, a substituted or unsubstituted C1 to C10 aliphatic organic group, or a substituted or unsubstituted C6 to C20 aromatic organic group,
n11 and n14 to n20 are independently an integer ranging from 0 to 4, and
n12, n13, n21, and n22 are independently an integer ranging from 0 to 3.

7. The composition for preparing an organic/inorganic hybrid poly(amide-imide) copolymer of claim 1 , wherein A of Chemical Formula 1 is selected from chemical formulae of Group 2:

8. The composition for preparing an organic/inorganic hybrid poly(amide-imide) copolymer of claim 1 , wherein B of Chemical Formula 1 is represented by Chemical Formula 6:

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

9. The composition for preparing an organic/inorganic hybrid poly(amide-imide) copolymer of claim 8 , wherein R 6 and R 7 are the same or different and are independently —CF 3 , —CCl 3 , —CBr 3 , —Cl 3 , —F, —Cl, —Br, —I, —NO 2 , —CN, —COCH 3 , or —CO 2 O 2 H 5 .

10. The composition for preparing an organic/inorganic hybrid poly(amide-imide) copolymer of claim 1 , wherein D of Chemical Formulae 2

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Jeon Hyunjeong
• Jee Sang Soo
• Choi Hongkyoon
• Sohn Byunghee
• Ju Kyeong Sik

Classifications

• C08K5/549

  containing silicon in a ring · CPC title

• C09D179/08

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

• C08L79/08 Primary

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

• C08J2483/06

  containing silicon bound to oxygen-containing groups (C08J2483/12 takes precedence) · CPC title

• C08J5/18

  Manufacture of films or sheets · CPC title