Poly(imide-amide) copolymer, a method of preparing a poly(imide-amide) copolymer, and an article including a poly(imide-amide) copolymer
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C08G-073/14
C09D-179/08
출원번호
US-0089083
(2013-11-25)
등록번호
US-9388279
(2016-07-12)
우선권정보
KR-10-2013-0101127 (2013-08-26)
발명자
/ 주소
Cho, Chung Kun
Androsov, Dmitry
Kalinina, Fedosya
Kovalev, Mikhail
출원인 / 주소
SAMSUNG ELECTRONICS CO., LTD.
대리인 / 주소
Cantor Colburn LLP
인용정보
피인용 횟수 :
1인용 특허 :
10
초록▼
A poly(imide-amide) copolymer, which is a product of a reaction between a diamine and a dianhydride, wherein the diamine comprises a diamine represented by Chemical Formula 1 and the dianhydride comprises a dianhydride represented by Chemical Formula 5: wherein, the variables in Chemical Formulae 1
A poly(imide-amide) copolymer, which is a product of a reaction between a diamine and a dianhydride, wherein the diamine comprises a diamine represented by Chemical Formula 1 and the dianhydride comprises a dianhydride represented by Chemical Formula 5: wherein, the variables in Chemical Formulae 1 and 5 are described in the specification.
대표청구항▼
1. A composition of preparing a poly(imide-amide) copolymer, comprising: (a) a first poly(imide-amide) oligomer comprising an amino group at both ends thereof, and(b) a second poly(imide-amide) oligomer comprising an anhydride group at both ends thereof,wherein both the first and second poly(imide-a
1. A composition of preparing a poly(imide-amide) copolymer, comprising: (a) a first poly(imide-amide) oligomer comprising an amino group at both ends thereof, and(b) a second poly(imide-amide) oligomer comprising an anhydride group at both ends thereof,wherein both the first and second poly(imide-amide) oligomers are reaction products of a diamine and a dianhydride, wherein the diamine comprises a diamine represented by Chemical Formula 1 and the dianhydride comprises a dianhydride represented by Chemical Formula 5: wherein, in Chemical Formula 1,R1 and R2 are the same or different, and are each independently selected from a halogen, a hydroxyl group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C1 to C10 alkoxy group,n1 and n2 are the same or different, and are each independently an integer from 0 to 4,Ar1 and Ar2 are the same or different and are each independently represented by Chemical Formula 2, 3, or 4: wherein, in Chemical Formula 2,Ra 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 group,R3 and R4 are the same or different and are each independently a halogen, a hydroxyl group, a substituted or unsubstituted C1 to C10 aliphatic group, a substituted or unsubstituted C6 to C20 aromatic group, an alkoxy group of formula —OR200, wherein R200 is a C1 to C10 aliphatic organic group, or a silyl group of formula —SiR201R202R203, wherein R201, R202, and R203 are the same or different and are each independently a hydrogen or a C1 to C10 aliphatic organic group, andn1 and n2 are the same or different and are each independently an integer ranging from 0 to 4, wherein, in Chemical Formula 3,R6 and R7 are the same or different and are each independently an electron withdrawing group,R8 and R9 are the same or different, and are each 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 —OR204, wherein R204 is a C1 to C10 aliphatic organic group, or a silyl group of formula —SiR205R206R207, wherein R205, R206, and R207 are the same or different, and are each independently a hydrogen, or 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,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 4,R14 is —O—, —S—, —C(═O)—, —CH(OH)—, —S(═O)2—, —Si(CH3)2—, —(CH2)p—, wherein 1≦p≦10, —(CF2)q—, wherein 1≦q≦10, —C(CH3)2—, —C(CF3)2—, and —C(═O)NH—, or a substituted or unsubstituted C6 to C30 aromatic organic group, wherein the aromatic organic group is 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(CH3)2—, —(CH2)p— wherein 1≦p≦10, —(CF2)q— wherein 1≦q≦10, —C(CH3)2—, —C(CF3)2—, and —C(═O)NH—,R16 and R17 are the same or different, and are each 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 —OR212, wherein R212 is a C1 to C10 aliphatic organic group, or a silyl group of formula —SiR213R214R215, wherein R213, R214, and R215 are the same or different, and are each independently a hydrogen or a C1 to C10 aliphatic organic group, andn9 and n10 are each independently an integer ranging from 0 to 4, in Chemical Formula 5,R10 is a substituted or unsubstituted C1 to C30 aliphatic 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 group,R12 and R13 are the same or different and are each independently a halogen, a hydroxyl group, a substituted or unsubstituted C1 to C10 aliphatic group, a substituted or unsubstituted C6 to C20 aromatic group, an alkoxy group of formula —OR205, wherein R205 is a C1 to C10 aliphatic organic group, or a silyl group of formula —SiR209R210R211, wherein R209, R210, and R211 are the same or different and are each independently a hydrogen, or a C1 to C10 aliphatic organic group, andn7 and n8 are the same or different and are each independently an integer ranging from 0 to 3. 2. The composition of preparing a poly(imide-amide) copolymer according to claim 1, wherein the dianhydride represented by Chemical Formula 5 comprises a dianhydride represented by Chemical Formula 6, Chemical Formula 7, or a combination thereof: in Chemical Formulae 6 and 7,R12 and R13 are the same or different, and are each independently a halogen, a hydroxy group, a substituted or unsubstituted C1 to C10 aliphatic organic group, a C6 to C20 aromatic organic group, an alkoxy group of formula —OR208, wherein R208 is a C1 to C10 aliphatic organic group, or a silyl group of formula —SiR209R210R211, wherein R209, R210, and R211 are the same or different, and are each independently hydrogen or a C1 to C10 aliphatic organic group, andn7 and n8 are each independently integers ranging from 0 to 3. 3. The composition of preparing a poly(imide-amide) copolymer according to claim 1, wherein the diamine further comprises a diamine represented by Chemical Formula 2-1, Chemical Formula 3-1, Chemical Formula 4-1, or a combination thereof: wherein, in Chemical Formula 2-1,Ra 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 group,R3 and R4 are the same or different and are each independently a halogen, a hydroxyl group, a substituted or unsubstituted C1 to C10 aliphatic group, a substituted or unsubstituted C6 to C20 aromatic group, an alkoxy group of formula —OR200, wherein R200 is a C1 to C10 aliphatic organic group, or a silyl group of formula —SiR201R202R203, wherein R201, R202, and R203 are the same or different and are each independently a hydrogen or a C1 to C10 aliphatic organic group, andn1 and n2 are the same or different and are independently an integer ranging from 0 to 4, wherein, in Chemical Formula 3-1,R6 and R7 are the same or different and are each independently an electron withdrawing group,R8 and R9 are the same or different, and are each 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 —OR264, wherein R204 is a C1 to C10 aliphatic organic group, or a silyl group of formula —SiR205R206R207, wherein R205, R206, and R207 are the same or different, and are each independently a hydrogen, or 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, andn4 is an integer ranging from 1 to 4,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 4-1,R14 is —O—, —S—, —C(═O)—, —CH(OH)—, —S(═O)2—, —Si(CH3)2—, —(CH2)p—, wherein 1≦p≦10, —(CF2)q—, wherein 1≦q≦10,—C(CH3)2—, —C(CF3)2—, and —C(═O)NH—, or a substituted or unsubstituted C6 to C30 aromatic organic group, wherein the aromatic organic group is 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(CH3)2—, —(CH2)p—, wherein 1≦p≦10, —(CF2)q—, wherein 1≦q≦10, —C(CH3)2—, —C(CF3)2—, and —C(═O)NH—,R16 and R17 are the same or different, and are each 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 —OR212, wherein R212 is a C1 to C10 aliphatic organic group, or a silyl group of formula —SiR213R214R215, wherein R213, R214, and R215 are the same or different, and are each independently a hydrogen or a C1 to C10 aliphatic organic group, andn9 and n10 are each independently an integer ranging from 0 to 4. 4. The composition of preparing a poly(imide-amide) copolymer according to claim 3, wherein Ra in Chemical Formula 2 and Chemical Formula 2-1 is independently selected from chemical formulae: R6 and R7 in Chemical Formula 3 and Chemical Formula 3-1 are the same or different, and are each independently selected from —CF3, —CCl3, —CBr3, —Cl3, —NO2, —CN, —C(═O)CH3, and —CO2C2H5, andR14 in Chemical Formula 4 and Chemical Formula 4-1 is SO2, and both n9 and n10 in Chemical Formula 4 and Chemical Formula 4-1 are the integer of 0. 5. The composition of preparing a poly(imide-amide) copolymer according to claim 4, wherein the reaction products of a diamine and a dianhydride are the reaction products of a reaction among a diamine represented by Chemical Formula 1, a diamine represented by Chemical Formula 3-1, and a dianhydride represented by Chemical Formula 6, Chemical Formula 7, or a combination thereof, wherein in Chemical Formula 1, both n1 and n2 are 0, and both Ar1 and Ar2 are represented by Chemical Formula 3, wherein in Chemical Formula 3, both R6 and R7 are —CF3, both n3 and n4 are 1, and both n5 and n6 are 0,wherein in Chemical Formula 3-1, both R6 and R7 are —CF3, both n3 and n4 are 1, and both n5 and n6 are 0, andwherein in Chemical Formula 6, Chemical Formula 7, or a combination thereof, both n7 and n8 are 0. 6. An article comprising a poly(imide-amide) copolymer prepared by a method comprising reacting a diamine comprising a diamine represented by Chemical Formula 1 with a dianhydride comprising a dianhydride represented by Chemical Formula 5 to separately prepare a poly(imide-amide) oligomer comprising an amino group at both ends thereof and a poly(imide-amide) oligomer comprising an anhydride group at both ends thereof,mixing the separately prepared poly(imide-amide) oligomer comprising an amino group at both ends thereof and a poly(imide-amide) oligomer comprising an anhydride group at both ends thereof to provide a mixture, andcuring the mixture: wherein, in Chemical Formula 1,R1 and R2 are the same or different, and are each independently selected from a halogen, a hydroxyl group, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C1 to C10 alkoxy group,n1 and n2 are the same or different, and are each independently an integer from 0 to 4,Ar1 and Ar2 are the same or different and are each independently represented by Chemical Formula 2, Chemical Formula 3, or Chemical Formula 4: wherein, in Chemical Formula 2,Ra 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 group,R3 and R4 are the same or different and are each independently a halogen, a hydroxyl group, a substituted or unsubstituted C1 to C10 aliphatic group, a substituted or unsubstituted C6 to C20 aromatic group, an alkoxy group of formula —OR200, wherein R200 is a C1 to C10 aliphatic organic group, or a silyl group of formula —SiR201R202R203, wherein R201, R202, and R203 are the same or different and are each independently a hydrogen or a C1 to C10 aliphatic organic group, andn1 and n2 are the same or different and are each independently an integer ranging from 0 to 4, wherein, in Chemical Formula 3,R6 and R7 are the same or different and are each independently an electron withdrawing group,R8 and R9 are the same or different, and are each 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 —OR204, wherein R204 is a C1 to C10 aliphatic organic group, or a silyl group of formula —SiR205R206R207, wherein R205, R206, and R207 are the same or different, and are each independently a hydrogen or 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,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 4,R14 is —O—, —S—, —C(═O)—, —CH(OH)—, —S(═O)2—, —Si(CH3)2—, —(CH2)p—, wherein 1≦p≦10, —(CF2)q—, wherein 1≦q≦10, —C(CH3)2—, —C(CF3)2—, and —C(═O)NH—, or a substituted or unsubstituted C6 to C30 aromatic organic group, wherein the aromatic organic group is 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(CH3)2—, —(CH2)p—, wherein 1≦p≦10, —(CF2)q—, wherein 1≦q≦10, —C(CH3)2—, —C(CF3)2—, and —C(═O)NH—,R16 and R17 are the same or different, and are each 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 —OR212, wherein R212 is a C1 to C10 aliphatic organic group, or a silyl group of formula —SiR213R214R215, wherein R213, R214, and R215 are the same or different, and are each independently a hydrogen or a C1 to C10 aliphatic organic group, andn9 and n10 are each independently an integer ranging from 0 to 4, and wherein, in Chemical Formula 5,R10 is a substituted or unsubstituted C1 to C30 aliphatic 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 group,R12 and R13 are the same or different and are each independently a halogen, a hydroxyl group, a substituted or unsubstituted C1 to C10 aliphatic group, a substituted or unsubstituted C6 to C20 aromatic group, an alkoxy group of formula —OR205, wherein R205 is a C1 to C10 aliphatic organic group, or a silyl group of formula —SiR209R210R211, wherein R209, R210, and R211 are the same or different and are each independently a hydrogen, or a C1 to C10 aliphatic organic group, andn7 and n8 are the same or different and are each independently an integer ranging from 0 to 3. 7. A display device comprising the article according to claim 6. 8. The composition of preparing a poly(imide-amide) copolymer according to claim 1, wherein the second poly(imide-amide) oligomer comprising an anhydride group at both ends thereof has a larger weight average molecular weight than the first poly(imide-amide) oligomer comprising an amino group at both ends thereof. 9. The composition of preparing a poly(imide-amide) copolymer according to claim 8, wherein the ratio of the weight average molecular weight of the first poly(imide-amide) oligomer comprising an amino group at both ends thereof to the weight average molecular weight of the second poly(imide-amide) oligomer comprising an anhydride group at both ends thereof is about 0.7 to about 0.95.
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