Composition of preparing poly(imide-benzoxazole) copolymer, poly(imide-benzoxazole) copolymer, article containing poly(imide-benzoxazole) copolymer, and display device including same

Patent metadata

Field	Value
Publication number	US-10858482-B2
Application number	US-201514879287-A
Country	US
Kind code	B2
Filing date	Oct 9, 2015
Priority date	Feb 12, 2015
Publication date	Dec 8, 2020
Grant date	Dec 8, 2020

Abstract

A composition for preparing poly(imide-benzoxazole) copolymer is described, where the copolymer include: a tetracarboxylic acid dianhydride represented by Chemical Formula 1, a diamine represented by Chemical Formula 2, and a diamine represented by Chemical Formula 3:

wherein definitions of groups and variables in Chemical Formulae 1 to 3 are the same as described in the specification.

First claim

What is claimed is:

1. A composition for preparing a poly(imide-benzoxazole) copolymer, comprising:
a tetracarboxylic acid dianhydride comprising a combination of 3,3′4,4′-biphenyl tetracarboxylic dianhydride and 4,4′-(hexafluoroisopropylidene)diphthalic anhydride,
a diamine comprising 2,2′-bis(fluoromethyl)benzidine, and
a diamine represented by Chemical Formula 3:

wherein in Chemical Formula 3,
L 1 is a phenylene group, and L 2 is a single bond,
wherein the mole ratio of the tetracarboxylic acid dianhydride to the total moles of the diamine comprising 2,2′-bis(fluoromethyl)benzidine and the diamine represented by Chemical Formula 3 is about 1:1, and wherein an amount of the diamine represented by Chemical Formula 3 is 1 mole percent to 5 mole percent based on the total mole number of the diamine comprising 2,2′-bis(fluoromethyl)benzidine and the diamine represented by Chemical Formula 3.

2. The composition for preparing the poly(imide-benzoxazole) copolymer according to claim 1 , wherein the tetracarboxylic acid dianhydride further comprises one or more selected from bicyclo[2.2.2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride, 3,3′,4,4′-diphenylsulfone tetracarboxylic dianhydride, 4,4′-oxydiphthalic anhydride, pyromellitic dianhydride, 4-(2,5-dioxotetrahydrofuran-3-yl)-1,2,3,4-tetrahydronaphthalene-1,2-dicarboxylic anhydride, and bis(3,4-dicarboxyphenyl)sulfone dianhydride.

3. The composition for preparing the poly(imide-benzoxazole) copolymer according to claim 1 ,
wherein in the tetracarboxylic acid dianhydride 3,3′,4,4′-biphenyl tetracarboxylic dianhydride is present in an amount of about 10 mole percent to about 55 mole percent and 4,4′-(hexafluoroisopropylidene)diphthalic anhydride is present in an amount of about 90 mole percent to about 45 mole percent.

4. A poly(imide-benzoxazole) copolymer prepared from the composition according to claim 1 .

5. A poly(imide-benzoxazole) copolymer comprising:
(i) a structural unit represented by Chemical Formula 4, Chemical Formula 5, or a combination thereof; and
(ii) a structural unit represented by Chemical Formula 6, Chemical Formula 7, or a combination thereof:

wherein in Chemical Formulae 4 to 7,
R 1 is represented by Chemical Formula 8 and Chemical Formula 9:

wherein in Chemical Formula 8,
R 10 is C(CF 3 ) 2 ,
wherein in Chemical Formulae 4 and 5, R 2 is represented by Chemical Formula 13,

wherein in Chemical Formulae 6 and 7,
L 1 is a phenylene group, and L 2 is a single bond,
wherein an amount of the structural unit represented by Chemical Formula 6, Chemical Formula 7, or a combination thereof is 1 mole percent to 5 mole percent based on the mole number of the total structural units in the poly(imide-benzoxazole) copolymer.

6. The poly(imide-benzoxazole) copolymer according to claim 5 ,
wherein R 1 in Chemical Formulae 4 to 7 comprises the structural unit represented by Chemical Formula 8 in an amount of about 90 mole percent to about 45 mole percent, and the structural unit represented by Chemical Formula 9 in an amount of about 10 mole percent to about 55 mole percent.

7. The poly(imide-benzoxazole) copolymer according to claim 5 , further comprising one or more structural units selected from the structural units represented by Chemical Formulae 14 to 17:

wherein in Chemical Formula 14,
R a is a substituted or unsubstituted C3 to C30 alicyclic organic group, a substituted or unsubstituted C6 to C30 aromatic organic group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a substituted or unsubstituted C13 to C20 fluorenylene group,
R 11 is a substituted or unsubstituted C6 to C30 aromatic organic group,
R 3 and R 4 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 200 , wherein R 200 is a C1 to C10 aliphatic organic group, 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 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 15,
R 5 is a substituted or unsubstituted C6 to C30 aromatic organic group,
R 6 and R 7 are the same or different and each are independently an electron withdrawing group selected from —CF 3 , —CCl 3 , —CBr 3 , —Cl 3 , —F, —Cl, —Br, —I, —NO 2 , —CN, —COCH 3 , and —CO 2 C 2 H 5 ,
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 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 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 16,
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 includes one aromatic ring, two or more aromatic rings fused together to provide a condensed ring system, or two or more aromatic 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(CH 3 ) 2 , C(CF 3 ) 2 , and C(═O)NH,
R 15 is a substituted or unsubstituted C6 to C30 aromatic organic group,
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 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 C1 to C10 aliphatic organic group, and
n9 and n10 are each independently an integer ranging from 0 to 4;

wherein in Chemical Formula 17,
R 18 is O, S,

Assignees

• Samsung Electronics Co Ltd
• Samsung Sdi Co Ltd

Inventors

• Hong Sung Woo
• Sohn Byung-Hee
• Song Sun Jin
• Ahn Chanjae
• Ju Kyeong-Sik
• Choi Sungwon

Classifications

• C08G73/22 Primary

  Polybenzoxazoles · CPC title

• Y10T428/31721

  Of polyimide · CPC title

• C08G73/1085

  Polyimides with diamino moieties or tetracarboxylic segments containing heterocyclic moieties · CPC title

• C08G73/14

  Polyamide-imides · CPC title

• C08G73/1067

  Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound · CPC title