Photosensitive resin composition, film prepared by using the photosensitive resin composition, and organic light-emitting display device including the film
A photosensitive resin composition includes a first binder resin represented by Formula 1. The photosensitive resin composition may be cured at a low temperature (e.g., about 0° C. to about 100° C., about 40° C. to about 100° C., or about 70° C. to about 100° C.). A film may be formed from the photosensitive resin composition. An organic light-emitting display (OLED) device may include the film prepared from the photosensitive resin composition.
1. A photosensitive resin composition comprising:
a first binder resin represented by Formula 1:
and
a second binder resin comprising an epoxy resin,
wherein, in Formula 1,
R 1 to R 4 and R 11 to R 13 are each independently selected from hydrogen, deuterium, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 1 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 6 -C 30 arylthio group, and a substituted or unsubstituted C 1 -C 30 heteroaryl group,
R 5 to R 7 are each independently a group including an unsaturated ethylene group,
the group including the unsaturated ethylene group does not include a phthalate group,
a1 and a11 to a13 are each independently an integer of 1 to 5,
a2 is an integer of 0 to 5,
b11 to b13 are each independently an integer of 0 to 3,
k1, k2, k3, m, and n are each independently a molar ratio in a corresponding repeating unit,
the sum of k1 and k2 is an integer of 1 to 20,
k3 is an integer of 1 to 10,
m and n are each independently an integer of 1 to 10, and
at least one substituent of the substituted C 1 -C 20 alkyl group, the substituted C 2 -C 20 alkenyl group, the substituted C 2 -C 20 alkynyl group, the substituted C 1 -C 20 alkoxy group, the substituted C 3 -C 10 cycloalkyl group, the substituted C 1 -C 10 heterocycloalkyl group, the substituted C 3 -C 10 cycloalkenyl group, the substituted C 1 -C 10 heterocycloalkenyl group, the substituted C 6 -C 30 aryl group, the substituted C 6 -C 30 aryloxy group, the substituted C 6 -C 30 arylthio group, and the substituted C 1 -C 30 heteroaryl group is selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, an epoxy group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 alkynyl group, a C 1 -C 6 alkoxy group, and a C 6 -C 20 aryl group.
2. The photosensitive resin composition of claim 1 , wherein, in Formula 1, R 1 to R 4 and R 11 to R 13 are each independently hydrogen, deuterium, or a substituted or unsubstituted C 1 -C 20 alkyl group.
3. The photosensitive resin composition of claim 1 , wherein, in Formula 1,
R 5 to R 7 are each independently a group represented by *—R a OC(═O)CH═CH 2 ,
R a is a substituted or unsubstituted C 1 -C 20 alkylene group,
at least one substituent of the substituted C 1 -C 20 alkylene group is selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, an epoxy group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C 1 -C 6 alkyl group, a C 2 -C 6 alkenyl group, a C 2 -C 6 alkynyl group, a C 1 -C 6 alkoxy group, and a C 6 -C 20 aryl group, and
* indicates a binding site to a neighboring atom.
4. The photosensitive resin composition of claim 1 , wherein, in Formula 1, a molar ratio of m:n is in a range of about 10:90 to about 50:50.
5. The photosensitive resin composition of claim 1 , wherein an acid value of the first binder resin is in a range of about 50 mgKOH/g to about 120 mgKOH/g.
6. The photosensitive resin composition of claim 1 , wherein an amount of the first binder resin is in a range of about 3 wt % to about 30 wt % based on the total weight of the photosensitive resin composition.
7. The photosensitive resin composition of claim 1 , wherein the second binder resin is represented by Formula 2:
wherein, in Formula 2,
R 21 to R 24 are each independently selected from hydrogen, deuterium, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, and a substituted or unsubstituted C 1 -C 20 alkoxy group,
R 25 and R 26 are each independently selected from hydrogen, deuterium, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 6 -C 30 arylthio group, and a substituted or unsubstituted C 1 -C 30 heteroaryl group,
R 27 is selected from hydrogen, deuterium, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 6 -C 30 arylthio group, a substituted or unsubstituted heteroaryl group, and a group represented by Formula 3,
b1 and b2 are each independently an integer of 0 to 4,
p and q are each independently a molar ratio of a corresponding repeating unit,
p is an integer of 5 to 300,
q is an integer of 0 to 20, and
in Formula 3,
R 31 and R 32 are each independently selected from hydrogen, deuterium, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, and a substituted or unsubstituted C 1 -C 20 alkoxy group,
R 33 , R 34 , and R′ are each independently selected from hydrogen, deuterium, a substituted or unsubstituted C 1 -C 20 alkyl group, a substituted or unsubstituted C 2 -C 20 alkenyl group, a substituted or unsubstituted C 2 -C 20 alkynyl group, a substituted or unsubstituted C 1 -C 20 alkoxy group, a substituted or unsubstituted C 6 -C 30 aryl group, a substituted or unsubstituted C 6 -C 30 aryloxy group, a substituted or unsubstituted C 6 -C 30 arylthio group, and a substituted or unsubstituted C 1 -C 30 heteroaryl group, and
c1 and c2 are each independently an integer of 0 to 4.
8. The photosensitive resin composition of claim 7 , wherein, in Formula 2,
R 23 to R 26 are each independently a substituted or unsubstituted C 1 -C 20 alkyl group, and R 27 is a group represented by Formula 3, and
in Formula 3,
R′ is a C 1 -C 20 alkyl group substituted with an epoxy group or a C 6 -C 30 aryl group substituted with an epoxy group,
p is an integer of 10 to 300, and
q is an integer of 3 to 20.
9. The photosensitive resin composition of claim 7 , wherein the second binder resin is represented by Formula 2-1:
10. The photosensitive resin composition of claim 1 , wherein an amount of the second binder resin is in a range of about 1 wt % to about 10 wt % based on the total weight of the photosensitive resin composition.
11. The photosensitive resin composition of claim 1 , wherein the photosensitive resin composition further comprises at least one selected from a photo cross-linking agent, a thermal curing agent, a photoinitiator, a pigment, and a solvent.
12. The photosensitive resin composition of claim 11 , wherein the photo cross-linking agent comprises at least one monomer selected from a urethane monomer and a cross-linking monomer having a group comprising an unsaturated ethylene group.
13. The photosensitive resin composition of claim 11 , wherein a weight ratio of the photo cross-linking agent to the first binder resin is in a range of about 1:0.6 to about 1:2.5.
14. The photosensitive resin composition of claim 11 , wherein an amount of the photo cross-linking agent is in a range of about 3 wt % to about 15 wt % based on the total weight of the photosensitive resin composition.
15. The photosensitive resin composition of claim 12 , wherein the photo cross-linking agent further comprises a monomer comprising a thiol group.
16. The photosensitive resin composition of claim 11 , wherein the thermal curing agent comprises at least one selected from a compound comprising an aromatic amine group, a compound comprising an alicyclic amine group, an aromatic amine-based a compound comprising an aromatic amine group, based a compound comprising a carboxylic acid group, a compound comprising an acid anhydride group, a compound comprising a polyphenol group, and a compound comprising an imidazole group.
17. The photosensitive resin composition of claim 11 , wherein the photoinitiator comprises at least one selected from a compound comprising an oxime group, a compound comprising a triazine group, a compound comprising a benzoin group, a compound comprising an acetophenone group, a compound comprising a xanthone group, and a compound comprising an imidazole group.
18. A film formed by curing the photosensitive resin composition of claim 1 .
19. An organic light-emitting display device comprising the film of claim 18 .