Compound, polymer, film, and optical device
A monomer represented by Chemical Formula 1: wherein, in Chemical Formula 1, R 1 , R 2 , o, p, A 1 , R a , m, k and n are the same as defined in the detailed description.
1. A compound represented by Chemical Formula 1:
wherein, in Chemical Formula 1,
R 1 and R 2 are independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 acyl group, a hydroxy group, a halogen, a nitro group, —NR′R″, —SiR′R″R″′ (wherein R′, R″, and R″′ are independently hydrogen, a C1 to C30 alkyl group, or a C6 to C30 aryl group), or a combination thereof,
o and p are independently an integer ranging from 0 to 3,
A 1 is a C6 to C30 aromatic ring,
R a is hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a hydroxy group, a halogen, a nitro group, —NR′R″, —C(═O)—NR′R″, —SiR′R″R″′ (wherein R′, R″, and R″′ are independently hydrogen, a C1 to C30 alkyl group, a C6 to C30 aryl group, or a C7 to C30 arylalkyl group), or a group represented by Chemical Formula 2:
wherein, in Chemical Formula 2,
L 2 and L 3 are independently O, C(═O), C(═O)O, C≡C, or C(═O)NR b (wherein, R b is hydrogen or a C1 to C30 alkyl group),
A 2 and A 3 are independently a substituted or unsubstituted C6 to C30 aromatic ring, a substituted or unsubstituted fluorene ring, or a substituted or unsubstituted C7 to C30 arylalkyl group,
q and r are independently an integer ranging from 0 to 3, provided that q+r is an integer greater than or equal to 1,
m is an integer greater than or equal to 1, and
k and n are independently an integer greater than or equal to 0.
2. The compound according to claim 1 , wherein in Chemical Formula 1,
o and p are independently 0 or 1,
A 1 is a C6 to C20 aromatic ring,
R a is hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C7 to C20 arylalkyl group, a substituted or unsubstituted C2 to C20 heteroaryl group, a halogen, —NR′R″ (wherein R′, and R″ are independently hydrogen, a C1 to C30 alkyl group, a C6 to C30 aryl group, or a C7 to C30 arylalkyl group), or a group represented by Chemical Formula 2:
wherein, in Chemical Formula 2,
L 2 and L 3 are independently C(═O)O, C≡C, or C(═O)NR b (wherein, R b is hydrogen or a C1 to C20 alkyl group),
A 2 and A 3 are independently a substituted or unsubstituted C6 to C20 aromatic ring, a substituted or unsubstituted fluorene ring, or a substituted or unsubstituted C7 to C20 arylalkyl group,
q and r are independently an integer ranging from 0 to 2, provided that 1≤q+r≤2,
m is an integer ranging from 1 to 3, and
k and n are independently an integer ranging from 0 to 10.
3. The compound according to claim 1 , wherein in Chemical Formula 1,
both o and p are 0,
A 1 is a benzene ring,
R a is hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C7 to C20 arylalkyl group, a substituted or unsubstituted C2 to C20 heteroaryl group, a halogen, or a group represented by Chemical Formula 2:
wherein, in Chemical Formula 2,
L 2 and L 3 are independently C(═O)O, C≡C, or C(═O)NR b (wherein, R b is hydrogen or a C1 to C20 alkyl group),
A 2 and A 3 are independently a substituted or unsubstituted benzene ring, a substituted or unsubstituted fluorene ring, or a substituted or unsubstituted C7 to C20 arylalkyl group,
q and r are independently an integer ranging from 0 to 2, provided that 1≤q+r≤2,
m is 1 or 2, and
k and n are independently an integer ranging from 0 to 3.
4. The compound according to claim 1 , wherein the compound represented by Chemical Formula 1 is represented by Chemical Formula 3 or Chemical Formula 4:
wherein, in Chemical Formulae 3 and 4,
R 1 and R 2 are independently a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C1 to C30 acyl group, a hydroxy group, a halogen, a nitro group, —NR′R″, —SiR′R″R″′ (wherein R′, R″, and R″′ are independently hydrogen, a C1 to C30 alkyl group, or a C6 to C30 aryl group), or a combination thereof,
o and p are independently an integer ranging from 0 to 3,
A 1 is a C6 to C30 aromatic ring,
R a is hydrogen, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C7 to C30 arylalkyl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a hydroxy group, a halogen, a nitro group, —NR′R″, —C(═O)—NR′R″, —SiR′R″R″′ (wherein R′, R″, and R″′ are independently hydrogen, a C1 to C30 alkyl group, a C6 to C30 aryl group, or a C7 to C30 arylalkyl group), or a group represented by Chemical Formula 2:
wherein, in Chemical Formula 2,
L 2 and L 3 are independently O, C(═O), C(═O)O, C≡C, or C(═O)NR b (wherein, R b is hydrogen or a C1 to C30 alkyl group),
A 2 and A 3 are independently a substituted or unsubstituted C6 to C30 aromatic ring, a substituted or unsubstituted fluorene ring, or a substituted or unsubstituted C7 to C30 arylalkyl group,
q and r are independently an integer ranging from 0 to 3, provided that q+r is an integer greater than or equal to 1,
m is an integer greater than or equal to 1, and
k and n are independently an integer greater than or equal to 0.
5. The compound according to claim 4 , wherein in Chemical Formulae 3 and 4,
o and p are independently 0 or 1,
A 1 is a C6 to C30 aromatic ring,
R a is hydrogen, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group, a substituted or unsubstituted C7 to C20 arylalkyl group, a substituted or unsubstituted C2 to C20 heteroaryl group, a halogen, —NR′R″ (wherein R′, and R″ are independently hydrogen, a C1 to C30 alkyl group, a C6 to C30 aryl group, or a C7 to C30 arylalkyl group), or a group represented by Chemical Formula 2:
wherein, in Chemical Formula 2,
L 2 and L 3 are independently, C(═O)O, C≡C, or C(═O)NR b (wherein, R b is hydrogen or a C1 to C20 alkyl group),
A 2 and A 3 are independently a substituted or unsubstituted C6 to C20 aromatic ring, a substituted or unsubstituted fluorene ring, or a substituted or unsubstituted C7 to C20 arylalkyl group,
q and r are independently an integer ranging from 0 to 2, provided that 1≤q+r≤2,
m is an integer ranging from 1 to 3, and
k and n are independently an integer ranging from 0 to 10.
6. The compound according to claim 4 , wherein in Chemical Formulae 3 and 4,
both o and p are 0,
A 1 is a benzene ring,
R a is hydrogen, a substituted or unsubstituted C1 to C10 alkyl group, a substituted or unsubstituted C1 to C10 alkoxy group, a substituted or unsubstituted C2 to C10 heteroaryl group, a halogen, or a group represented by Chemical Formula 2:
wherein, in Chemical Formula 2,
L 2 and L 3 are independently, C(═O)O, C≡C, or C(═O)NR b (wherein, R b is hydrogen or a C1 to C20 alkyl group),
A 2 and A 3 are independently a substituted or unsubstituted benzene ring, a substituted or unsubstituted fluorene ring, or a substituted or unsubstituted C7 to C20 arylalkyl group,
q and r are independently an integer ranging from 0 to 2, provided that 1≤q+r≥2,
m is 1 or 2, and
k and n are independently an integer ranging from 0 to 3.
7. A polymer, which is a product of reactants comprising the compound according to claim 1 and a diamine.
8. The polymer according to claim 7 , wherein the diamine is represented by Chemical Formula 5:
NH 2 —R c —NH 2 Chemical Formula 5
wherein in Chemical Formula 5,
R c is a substituted or unsubstituted C6 to C30 aromatic organic group, wherein the substituted or unsubstituted C6 to C30 aromatic organic group is present as a substituted or unsubstituted single aromatic ring; a fused ring comprising two or more substituted or unsubstituted aromatic rings; or a ring system comprising two or more of the substituted or unsubstituted single aromatic ring and/or the fused ring that are linked by a single bond, or a functional group selected from a fluorenylene group, a substituted or unsubstituted C1 to C10 cycloalkylene group, a substituted or unsubstituted C6 to C15 arylene 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 —, —C(═O)NH—, or a combination thereof.
9. The polymer according to claim 8 , wherein the diamine represented by Chemical Formula 5 is represented by at least one of Chemical Formula 6 to Chemical Formula 8:
wherein, in Chemical Formula 6,
R d is selected from the following chemical formulae:
R 7 and R 8 are the same or different and are independently a halogen, a hydroxy group, an alkoxy group (—OR 200 , wherein R 200 is a C1 to C10 aliphatic organic group), a silyl group (—SiR 201 R 202 R 203 , wherein R 201 , R 202 , and R 203 are the same or different and are independently hydrogen or a C1 to C10 aliphatic organic group), a substituted or unsubstituted C1 to C10 aliphatic organic group, or a substituted or unsubstituted C6 to C20 aromatic organic group, and
n1 and n2 are independently an integer ranging from 0 to 4;
wherein, in Chemical Formula 7,
R 26 and R 27 are the same or different and are independently an electron withdrawing group selected from —CF 3 , —CCl 3 , —CBr 3 , —Cl 3 , —NO 2 , —CN, —COCH 3 , or —CO 2 C 2 H 5 ,
R 28 and R 29 are the same or different and are independently a halogen, a hydroxy group, 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 or different and are independently hydrogen or a C1 to C10 aliphatic organic group), a substituted or unsubstituted C1 to C10 aliphatic organic group, or a substituted or unsubstituted C6 to C20 aromatic organic group,
n3 is an integer ranging from 1 to 4, and n5 is an integer ranging from 0 to 3, provided that n3+n5 is an integer ranging from 1 to 4, and
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 8,
R 14 comprises 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 C18 aromatic organic group, wherein the substituted or unsubstituted C6 to C18 aromatic organic group is present as a single aromatic ring, a fused ring comprising two or more aromatic rings, or a ring system comprising two or more of the single aromatic ring and/or the fused ring that are linked by a single bond or 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 , or C(═O)NH,
R 16 and R 17 are the same or different and are independently a halogen, a hydroxy group, an alkoxy group (—OR 212 , wherein R 212 is a C1 to C10 aliphatic organic group), a silyl group (—SiR 213 R 214 R 215 , wherein R 213 , R 214 , and R 215 are the same or different and are independently hydrogen or a C1 to C10 aliphatic organic group), a substituted or unsubstituted C1 to C10 aliphatic organic group, or a substituted or unsubstituted C6 to C20 aromatic organic group, and
n9 and n10 are independently an integer ranging from 0 to 4.
10. The polymer according to claim 9 , wherein the diamine represented by Chemical Formula 5 comprises at least one of the diamine represented by Chemical Formula 7 and the diamine represented by Chemical Formula 8.
11. The polymer according to claim 10 , wherein the diamine represented by Chemical Formula 7 comprises 2,2′-bis(trifluoromethyl)benzidine (TFDB), and the diamine represented by Chemical Formula 8 comprises 4,4′-diaminodiphenyl sulfone (DADPS).
12. The polymer according to claim 7 , wherein the reactants further comprises a dianhydride represented by Chemical Formula 9:
wherein in Chemical Formula 9,
R 10 is a single bond, —O—, —S—, —C(═O)—, —CH(OH)—, —C(═O)NH—, —S(═O) 2 —, —Si(CH 3 ) 2 —, —(CH 2 ) p —, —(CF 2 ) q —, —C(C n H 2n+1 ) 2 —, —C(C n F 2n+1 ) 2 —, —(CH 2 ) p —C(C n H 2n+1 ) 2 —(CH 2 ) q —, or —CH 2 ) p —C(C n F 2n+1 ) 2 —(CH 2 ) q — (wherein 1≤n≤10, 1≤p≤10, and 1≤q≤10),
R 12 and R 13 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, a —OR 201 group (wherein R 201 is a C1 to C10 aliphatic organic group), or a —SiR 210 R 211 R 212 (wherein R 210 , R 211 , and R 212 are independently hydrogen or a C1 to C10 aliphatic organic group) group, and
n7 and n8 are independently one of integers of 0 to 3.
13. The polymer according to claim 12 , wherein the dianhydride represented by Chemical Formula 9 comprises a dianhydride represented by Chemical Formula 10, a dianhydride represented by Chemical Formula 11, or a combination thereof:
wherein, in Chemical Formulae 10 and 11,
R 12 and R 13 are the same or different and are independently a halogen, a hydroxy group, an alkoxy group (—OR 208 , wherein R 208 is a C1 to C10 aliphatic organic group), a silyl group (—SiR 209 R 210 R 211 , wherein R 209 , R 210 , and R 211 are the same or different and are independently hydrogen or a C1 to C10 aliphatic organic group), a substituted or unsubstituted C1 to C10 aliphatic organic group, or a substituted or unsubstituted C6 to C20 aromatic organic group, and
n7 and n8 are independently an integer ranging from 0 to 3.
14. The polymer according to claim 13 , wherein at least one of the dianhydride represented by Chemical Formula 10 and the dianhydride represented by Chemical Formula 11 is comprised in an amount of about 1 mole percent to about 99 mole percent based on the total mole number of the dianhydrides.
15. The polymer according to claim 7 , wherein the reactants further comprises a dicarboxylic acid derivative represented by Chemical Formula 12:
wherein, in Chemical Formula 12,
R 3 is at least one of a substituted or unsubstituted phenylene group and a substituted or unsubstituted biphenylene group, and each X is the same or different and is a halogen atom.
16. The polymer according to claim 15 , wherein R 3 of Chemical Formula 12 is at least one of an unsubstituted phenylene group and an unsubstituted biphenylene group, and each X is independently Cl or Br.
17. A film comprising the polymer according to claim 7 .
18. The film according to claim 17 , wherein the film is a compensation film.
19. An optical device comprising the film according to claim 17 .
20. The optical device according to claim 19 , wherein the optical device is a display device.