Photopatternable materials and related electronic devices and methods
View Patent ↗Described herein is a solution-processable composition for preparing a photopatternable material. The solution-processable composition generally includes (a) an oligomeric siloxane component that includes, based on its total weight, between about 40% by weight and about 100% by weight one or more cage-structured polyhedral oligomeric silsesquioxanes that are functionalized with one or more crosslinkable moieties such as cycloaliphatic epoxy moieties, (b) a polymerization initiator; (c) one or more thermosettable polymers that collectively are present in an amount between about 1% by weight and about 20% by weight based on the total weight of the oligomeric siloxane component; and (d) a solvent.
1. A solution-processable composition for preparing a photopatternable material, the composition comprising:
(a) an oligomeric siloxane component, wherein the oligomeric siloxane component comprises, based on its total weight, between about 40% by weight and about 100% by weight one or more cage-structured polyhedral oligomeric silsesquioxanes of the formula:
R 1 m R 2 n (SiO 1.5 ) q ,
wherein:
each R 1 comprises a cycloaliphatic epoxy moiety;
each R 2 independently is selected from the group consisting of H, F, a C 1-20 alkyl group, a C 1-20 fluoroalkyl group, a C 3-20 cycloalkyl group, a C 6-20 aryl group, and a C 7-20 arylakyl group;
q is 8, 10 or 12; and
m and n are integers, provided that m+n=q and m is at least 1;
(b) a polymerization initiator;
(c) one or more thermosettable polymers selected from the group consisting of polyisoprene, isobutylene isoprene rubber, polybutadiene, styrene-butadiene rubber, acrylonitrile butadiene rubber, hydrogenated nitrile rubbers, ethylene propylene copolymer, ethylene propylene diene rubber, polyacrylic rubber, fluorosilicone rubber, and ethylene-vinyl acetate, wherein the one or more thermosettable polymers collectively are present in an amount between about 1% by weight and about 20% by weight based on the total weight of the oligomeric siloxane component; and
(d) a solvent;
wherein the oligomeric siloxane component is present in an amount between about 40% and about 98% based on 100% by weight solids of the composition.
2. The composition of claim 1 , wherein said oligomeric siloxane component comprises, based on its total weight, less than about 40% by weight non-cage structured oligomeric siloxanes, and wherein said non-cage structured oligomeric siloxanes comprise one or more cycloaliphatic epoxy moieties.
3. The composition of claim 2 , wherein said non-cage structured oligomeric siloxanes comprise random-structured oligomeric siloxanes, ladder-structured oligomeric siloxanes, partially cage-structured oligomeric siloxanes, or combinations thereof.
4. The composition of claim 1 , wherein q is 8.
5. The composition of claim 1 , wherein the polymerization initiator is a photoinitiator.
6. The composition of claim 5 , wherein the photoinitiator is a free radical photoinitiator or a cationic photoinitiator.
7. The composition of claim 1 , wherein the thermosettable polymers collectively are present in an amount between about 1% and about 40% based on 100% by weight solids of the composition.
8. The composition of claim 1 , wherein the polymerization initiator is present in an amount between about 1% and about 8% based on 100% by weight solids of the composition.
9. The composition of claim 1 , wherein the solvent is present in an amount between about 20% by weight and about 80% by weight based on the total weight of the composition.
10. The composition of claim 1 further comprising one or more additives selected from the group consisting of a leveling agent, an adhesion promoter, a wetting agent, and a rheology modifier, wherein each of the one or more additives is present in an amount between about 1% and about 10% based on 100% by weight solids of the composition.
11. The composition of claim 1 , wherein the composition comprises a photocurable monomer or oligomer.
12. A solution-processable composition for preparing a photopatternable material, the composition comprising:
(a) an oligomeric siloxane component, wherein the oligomeric siloxane component comprises, based on its total weight, between about 40% by weight and about 100% by weight one or more cage-structured polyhedral oligomeric silsesquioxanes of the formula:
R 1 m R 2 n (SiO 1.5 ) q ,
wherein:
each R 1 comprises a cycloaliphatic epoxy moiety;
each R 2 independently is selected from the group consisting of H, F, a C 1-20 alkyl group, a C 1-20 fluoroalkyl group, a C 3-20 cycloalkyl group, a C 6-20 aryl group, and a C 7-20 arylakyl group;
q is 8, 10 or 12; and
m and n are integers, provided that m+n=q and m is at least 1;
(b) a polymerization initiator;
(c) one or more thermosettable polymers selected from the group consisting of polyisoprene, isobutylene isoprene rubber, polybutadiene, styrene-butadiene rubber, acrylonitrile butadiene rubber, hydrogenated nitrile rubbers, ethylene propylene copolymer, ethylene propylene diene rubber, polyacrylic rubber, fluorosilicone rubber, and ethylene-vinyl acetate, wherein the one or more thermosettable polymers collectively are present in an amount between about 1% by weight and about 20% by weight based on the total weight of the oligomeric siloxane component, and wherein each of the thermosettable polymers comprises in its backbone, as pendant groups, and/or as terminal groups one or more functional groups independently selected from the group consisting of a carboxylic acid group, an anhydride group, an amine group, a glycidyl ether group, a cycloaliphatic epoxy group, an acrylate group, and a methacrylate group; and
(d) a solvent.
13. The composition of claim 12 , wherein said oligomeric siloxane component comprises, based on its total weight, less than about 40% by weight non-cage structured oligomeric siloxanes, and wherein said non-cage structured oligomeric siloxanes comprise one or more cycloaliphatic epoxy moieties.
14. The composition of claim 13 , wherein said non-cage structured oligomeric siloxanes comprise random-structured oligomeric siloxanes, ladder-structured oligomeric siloxanes, partially cage-structured oligomeric siloxanes, or combinations thereof.
15. The composition of claim 12 , wherein q is 8.
16. The composition of claim 12 , wherein at least one of the following is true: (i) the thermosettable polymers collectively are present in an amount between about 1% and about 40% based on 100% by weight solids of the composition; (ii) the polymerization initiator is present in an amount between about 1% and about 8% based on 100% by weight solids of the composition; (iii) the solvent is present in an amount between about 20% by weight and about 80% by weight based on the total weight of the composition; and/or (iv) the oligomeric siloxane component is present in an amount between about 40% and about 98% based on 100% by weight solids of the composition.
17. The composition of claim 12 further comprising one or more additives selected from the group consisting of a leveling agent, an adhesion promoter, a wetting agent, and a rheology modifier, wherein each of the one or more additives is present in an amount between about 1% and about 10% based on 100% by weight solids of the composition.
18. The composition of claim 17 , wherein the leveling agent is a polysiloxane leveling agent and wherein the adhesion promoter is a trialkoxysilane adhesion promoter.
19. The composition of claim 12 , wherein the composition comprises a photocurable monomer or oligomer.
20. A solution-processable composition for preparing a photopatternable material, the composition comprising:
(a) an oligomeric siloxane component, wherein the oligomeric siloxane component comprises, based on its total weight, between about 40% by weight and about 100% by weight one or more cage-structured polyhedral oligomeric silsesquioxanes of the formula:
R 1 m R 2 n (SiO 1.5 ) q ,
wherein:
each R 1 comprises a cycloaliphatic epoxy moiety;
each R 2 independently is selected from the group consisting of H, F, a C 1-20 alkyl group, a C 1-20 fluoroalkyl group, a C 3-20 cycloalkyl group, a C 6-20 aryl group, and a C 7-20 arylakyl group;
q is 8, 10 or 12; and
m and n are integers, provided that m+n=q and m is at least 1;
(b) a polymerization initiator;
(c) one or more thermosettable polymers selected from the group consisting of polyisoprene, isobutylene isoprene rubber, polybutadiene, styrene-butadiene rubber, acrylonitrile butadiene rubber, hydrogenated nitrile rubbers, ethylene propylene copolymer, ethylene propylene diene rubber, polyacrylic rubber, fluorosilicone rubber, and ethylene-vinyl acetate, wherein the one or more thermosettable polymers collectively are present in an amount between about 1% by weight and about 20% by weight based on the total weight of the oligomeric siloxane component;
(d) a solvent; and at least one of:
(e) a polysiloxane leveling agent present in an amount between about 1% and about 10% by weight based on 100% weight solids of the composition; or
(f) a trialkoxysilane adhesion promoter selected from the group consisting of