Adhesive composition and adhesive film made therefrom
Disclosed is an adhesive composition including a compound having a multi-functional urethane (meth)acrylate group and an adhesive film prepared by using it. The adhesive composition includes compounds represented by Chemical Formulae 1 to 3. The compound represented by Chemical Formulae 1 to 3 includes an urethane (meth)acrylate group represented by the Chemical Formula 1-1 or 1-2.
1. An adhesive composition comprising:
a compound represented by the following Chemical Formulae 1, a photo polymerization initiator, and a solvent:
wherein in the above Chemical Formula 1, A is carbon (C) or silicon (Si), L 1 to L 4 are the same or different and are independently selected from the group consisting of a single bond, a C1 to C20 substituted or unsubstituted alkylene, and a C6 to C20 substituted or unsubstituted arylene, X 1 to X 4 are the same or different and are independently selected from the group consisting of hydrogen, a C1 to C5 alkyl, substituents represented by the following Chemical Formula 1-1 and substituents represented by the following Chemical Formula 1-2, provided that at least two X 1 to X 4 are selected from the group consisting of substituents represented by the following Chemical Formula 1-1 or 1-2, and a to d are independently integers of 1 or 2, and when each of a to d is 2, each of X 1 to X 4 is the same or different,
wherein in the above Chemical Formula 1-1, Z is selected from the group consisting of a single bond, —O—, —COO—, and —OCO—, j is an integer ranging from 1 to 5, h is an integer ranging from 0 to 5, and R 100 is hydrogen or a methyl, provided that when Z is —O—, —COO—, or —OCO—, h is not zero,
wherein in the above Chemical Formula 1-2, p and q are independently integers ranging from 1 to 5, and R 101 to R 103 are independently hydrogen or a methyl.
2. The adhesive composition of claim 1 , wherein the compound of Chemical Formula 1 comprises a compound represented by the following Chemical Formulae 1A:
wherein in the above Chemical Formula 1A, A is carbon (C) or silicon (Si), L 1 and L 4 are the same or different and are independently selected from the group consisting of a single bond, and a C1 to C20 alkylene, R 1 to R 4 are the same or different and are independently selected from the group consisting of hydrogen, a C1 to C5 alkyl, substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, X 2 and X 3 are independently selected from the group consisting of hydrogen, a C1 to C5 alkyl, substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, provided that at least two of R 1 to R 4 , X 2 and X 3 are selected from the group consisting of substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, and b and d are independently integers of 1 or 2, and when b and d are both equal to 2, each of X 2 and X 3 is the same or different.
3. The adhesive composition of claim 1 , wherein the compound of Chemical Formula 1 comprises a compound represented by the following Chemical Formulae 1B:
wherein in the above Chemical Formula 1B, A is carbon (C) or silicon (Si), L 1 is selected from the group consisting of a single bond and a C1 to C20 alkylene, R 13 to R 16 are the same or different and are independently selected from the group consisting of hydrogen, a C1 to C5 alkyl, substituents represented by the above Chemical Formula 1-1 or and substituents represented by the above Chemical Formula 1-2, X 2 to X 4 are the same or different and are independently selected from the group consisting of hydrogen, a C1 to C5 alkyl, substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, provided that at least two of R 13 to R 16 and X 2 to X 4 are selected from the group consisting of substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, and
b to d are independently integers of 1 or 2, and when each of b to d is 2, each of X 2 to X 4 is the same or different.
4. The adhesive composition of claim 1 , wherein the compound of Chemical Formula 1 comprises a compound represented by the following Chemical Formulae 1C:
wherein in the above Chemical Formula 1C, A is carbon (C) or silicon (Si), R 25 to R 28 are the same or different and are independently selected from the group consisting of hydrogen, a C1 to C5 alkyl, substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, X 1 to X 4 are independently selected from the group consisting of hydrogen, a C1 to C5 alkyl, substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, provided that at least two of R 25 to R 28 and X 1 to X 4 are selected from the group consisting of substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, and a to d are independently integers of 1 or 2, and when each of a to d is 2, each of X 1 to X 4 is the same or different.
5. The adhesive composition of claim 1 , wherein the compound of Chemical Formula 1 comprises a compound represented by the following Chemical Formulae 1D:
wherein in the above Chemical Formula 1D, A is carbon (C) or silicon (Si), L 1 ′ to L 4 ′ are the same or different and are independently selected from the group consisting of a single bond, and a C1 to C20 substituted or unsubstituted alkylene, X 1 to X 4 are the same or different and are independently selected from the group consisting of hydrogen, a C1 to C5 alkyl, substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, provided that at least two of X 1 to X 4 are selected from the group consisting of substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, and
a to d are independently integers of 1 or 2, and when each of a to d is 2, each of X 1 to X 4 is the same or different.
6. An adhesive composition comprising:
a compound represented by the following Chemical Formula 2, a photopolymerization initiator, and a solvent:
wherein in the above Chemical Formula 2,
L 5 to L 8 are the same or different and are independently selected from the group consisting of a single bond, a C1 to C20 substituted or unsubstituted alkylene, and a C6 to C20 substituted or unsubstituted arylene, X 5 to X 8 are the same or different and are independently selected from the group consisting of hydrogen, a C1 to C5 alkyl, substituents represented by the Chemical Formula 1-1 and substituents represented by the Chemical Formula 1-2, provided that at least two of X 5 to X 8 are selected from the group consisting of substituents represented by the above Chemical Formula 1-1 and substituents represented by the Chemical Formula 1-2, and e to h are independently integers of 1 or 2, and when each of e to h is 2, each of X 5 to X 8 is the same or different;
wherein in the above Chemical Formula 1-1, Z is selected from the group consisting of a single bond, —O—, —COO—, and —OCO—, j is an integer ranging from 1 to 5, h is an integer ranging from 0 to 5, and R 100 is hydrogen or a methyl, provided that when Z is —O—, —COO—, or —OCO—, h is not zero,
wherein in the above Chemical Formula 1-2, p and q are independently integers ranging from 1 to 5, and R 101 to R 103 are independently hydrogen or a methyl.
7. The adhesive composition of claim 6 , wherein the compound of Chemical Formula 2 comprises a compound represented by the following Chemical Formulae 2A:
wherein in the above Chemical Formula 2A, L 6 and L 7 are the same or different and are independently selected from the group consisting of a single bond, and a C1 to C20 alkylene, R 5 to R 8 are the same or different and are independently selected from the group consisting of hydrogen, a C1 to C5 alkyl, substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, X 5 and X 8 are the same or different and are independently selected from the group consisting of hydrogen, a C1 to C5 alkyl, substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, provided that at least two of R 5 to R 8 , and X 5 and X 8 are selected from the group consisting of substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, e and h are independently integers of 1 or 2, and when e and h are both equal to 2, each of X 5 and X 8 is the same or different.
8. The adhesive composition of claim 6 , wherein the compound of Chemical Formula 2 comprises a compound represented by the following Chemical Formulae 2B:
wherein in the above Chemical Formula 2B, L 6 is selected from the group consisting of a single bond and a C1 to C20 alkylene, R 17 to R 20 are the same or different and are independently selected from the group consisting of hydrogen, a C1 to C5 alkyl, substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, X 5 , X 7 , and X 8 are the same or different and are independently selected from the group consisting of hydrogen, a C1 to C5 alkyl, substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, provided that at least two of R 17 to R 20 , X 5 , X 7 , and X 8 are selected from the group consisting of substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, and e, g and h are independently integers of 1 or 2, and when each of e, g and h is 2, each of X 5 , X 7 and X 8 is the same or different.
9. The adhesive composition of claim 6 , wherein the compound of Chemical Formula 2 comprises a compound represented by the following Chemical Formulae 2C:
wherein in the above Chemical Formula 2C, R 29 to R 32 are the same or different and are independently selected from the group consisting of hydrogen, a C1 to C5 alkyl, substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, X 5 to X 8 are the same or different and are independently selected from the group consisting of hydrogen, a C1 to C5 alkyl, substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, provided that at least two of R 29 to R 32 , and X 5 to X 8 are selected from the group consisting of substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, and e to h are independently integers of 1 or 2, and when each of e to h is 2, each of X 5 to X 8 is the same or different.
10. The adhesive composition of claim 6 , wherein the compound of Chemical Formula 2 comprises a compound represented by the following Chemical Formulae 2D:
wherein in the above Chemical Formula 2D, L 5 ′ to L 8 ′ are the same or different and are independently selected from the group consisting of a single bond, and a C1 to C20 substituted or unsubstituted alkylene, X 5 to X 8 are the same or different and are independently selected from the group consisting of hydrogen, a C1 to C5 alkyl, substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, provided that at least two of X 5 to X 8 are substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, and e to h are independently integers of 1 or 2, and when each of e to h is 2, each of X 5 to X 8 is the same or different.
11. An adhesive composition comprising:
a compound represented by the following Chemical Formula 3, a photopolymerization initiator, and a solvent:
wherein in the above Chemical Formula 3, L 9 to L 12 are the same or different and are independently selected from the group consisting of a single bond, a C1 to C20 substituted or unsubstituted alkylene, and a C6 to C20 substituted or unsubstituted arylene, X 9 to X 12 are the same or different and are independently selected from the group consisting of hydrogen, a C1 to C5 alkyl, substituents represented by the Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, provided that at least two of X 9 to X 12 are selected from the group consisting of substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, and k to n are independently integers of 1 or 2, and when each of k to n is 2, each of X 9 to X 12 is the same or different;
wherein in the above Chemical Formula 1-1, Z is selected from the group consisting of a single bond, —O—, —COO—, and —OCO—, j is an integer ranging from 1 to 5, h is an integer ranging from 0 to 5, and R 100 is hydrogen or a methyl, provided that when Z is —O—, —COO—, or —OCO—, h is not zero,
wherein in the above Chemical Formula 1-2, p and q are independently integers ranging from 1 to 5, and R 101 to R 103 are independently hydrogen or a methyl.
12. The adhesive composition of claim 11 , wherein the compound of Chemical Formula 3 comprises a compound represented by the following Chemical Formulae 3A:
wherein in the above Chemical Formula 3A, L 10 and L 11 are the same or different and are independently selected from the group consisting of a single bond, and C1 to C20 alkylene, R 9 to R 12 are the same or different and are independently selected from the group consisting of hydrogen, a C1 to C5 alkyl, substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, X 9 and X 12 are independently selected from the group consisting of hydrogen, a C1 to C5 alkyl, substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, provided that at least two of R 9 to R 12 , X 9 and X 12 are selected from the group consisting of substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, k and n are independently integers of 1 or 2, and when k and n are both equal to 2, each of X 9 and X 12 is the same or different.
13. The adhesive composition of claim 11 , wherein the compound of Chemical Formula 3 comprises a compound represented by the following Chemical Formulae 3B:
wherein in the above Chemical Formula 3B, L 10 is selected from the group consisting of a single bond and a C1 to C20 alkylene, R 21 to R 24 are the same or different and are independently selected from the group consisting of hydrogen, a C1 to C5 alkyl, substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, X 9 , X 11 , and X 12 are independently selected from the group consisting of hydrogen, a C1 to C5 alkyl, substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, provided that R 21 to R 24 , X 9 , X 11 , and X 12 are selected from the group consisting of substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, and k, m, and n are independently integers of 1 or 2, and when k, m, and n are 2, each of X 9 , X 11 and X 12 is the same or different.
14. The adhesive composition of claim 11 , wherein the compound of Chemical Formula 3 comprises a compound represented by the following Chemical Formulae 3C:
wherein in the above Chemical Formula 3C, R 33 to R 36 are the same or different and are independently selected from the group consisting of hydrogen, a C1 to C5 alkyl, substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, X 9 to X 12 are the same or different and are independently selected from the group consisting of hydrogen, a C1 to C5 alkyl, substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, provided that at least two of R 33 to R 36 and X 9 to X 12 are selected from the group consisting of substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, and k to n are independently integers of 1 or 2, and when each of k to n is 2, each of X 9 to X 12 is the same or different.
15. The adhesive composition of claim 11 , wherein the compound of Chemical Formula 3 comprises a compound represented by the following Chemical Formulae 3D:
wherein in the above Chemical Formula 3D, L 9 ′ to L 12 ′ are the same or different and are independently selected from the group consisting of a single bond, and a C1 to C20 substituted or unsubstituted alkylene, X 9 to X 12 are the same or different and are independently selected from the group consisting of hydrogen, a C1 to C5 alkyl, substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, provided that at least two of X 9 to X 12 are selected from the group consisting of substituents represented by the above Chemical Formula 1-1 and substituents represented by the above Chemical Formula 1-2, and k to n are independently integers of 1 or 2, and when each of k to n is 2, each of X 9 to X 12 is the same or different.
16. The adhesive composition of claim 1 , wherein the photopolymerization initiator is selected from the group consisting of α-hydroxy ketone, benzyl ketal, benzyldimethylketal, benzophenone, acetophenone, benzoin, benzoinmethylether, benzomethylether, benzoinbenzoic acid, methylbenzoinbenzoate, 2,4-diethylthioxanthone, 1-hydroxy cyclohexylphenyl ketone, benzyldiphenyl sulfide, tetramethyl thiuram monosulfide, 2,2-dimethoxy-2-phenyl acetophenone, and a combination thereof.
17. The adhesive composition of claim 1 , wherein the adhesive composition further comprises a binder.
18. The adhesive composition of claim 17 , wherein the adhesive binder is selected from the group consisting of a polyester-based binder, an urethane-based binder, a silicon-based binder, a natural rubber-based binder, an acryl-based binder, and a combination thereof.
19. The adhesive composition of claim 1 , wherein at least three of X 1 to X 4 in the Chemical Formula 1 are selected from the group consisting of substituents represented by Chemical Formula 1-1 and substituents represented by Chemical Formula 1-2.
20. The adhesive composition of claim 6 , wherein at least three of X 5 to X 8 in the Chemical Formula 2 are selected from the group consisting of substituents represented by Chemical Formula 1-1 and substituents represented by Chemical Formula 1-2.
21. The adhesive composition of claim 11 , wherein at least three of X 9 to X 12 in the Chemical Formula 3 are selected from the group consisting of substituents represented by Chemical Formula 1-1 and substituents represented by Chemical Formula 1-2.
22. An adhesive film obtained by photocuring the adhesive composition according to claim 1 .
23. An adhesive film obtained by photocuring the adhesive composition according to claim 6 .
24. An adhesive film obtained by photocuring the adhesive composition according to claim 11 .