Photosensitive bismaleimide composition
The present disclosure relates to a photosensitive composition comprising a photoinitiator and a bismaleimide component, photopolymers comprising the photosensitive composition and their use, especially in electronic devices. The bismaleimide component includes a bismaleimide compound or a bismaleimide oligomer.
1. A photosensitive composition comprising a photoinitiator, a bismaleimide component, a polymerizable arylcyclobutene monomer, and at least one polymerizable nitrogen heterocycle containing monomer; wherein the photoinitiator is an oxime ester compound present from 0.5 to 25 percent by weight based on the weight of the bismaleimide component;
wherein the bismaleimide component comprises a bismaleimide compound or a bismaleimide oligomer;
wherein the bismaleimide compound is represented by a general formula (I):
where R is substituted or unsubstituted linking group selected from the group consisting of alkylene, alkylenearyl, cycloalkylene, cycloalkylenearyl, cycloalkylalkylene and combinations thereof; and R 1 is selected from the group consisting of hydrogen, deuterium, halogen, cyano, methyl, vinyl, allyl, isoprene, and combinations thereof;
wherein the bismaleimide oligomer is represented by a general Formula (II):
where R 2 is H or CH 3 ; R 3 is C 1 -C 40 alkyl, alkyl polydimethyl siloxane, or alkylaryl; R 4 is selected from the group consisting of
and combinations thereof; and n is an integer of 1 to 10; and wherein the arylcyclobutene monomer is represented by a general Formula (IV), (V), or (VI),
where:
K 1 is a divalent group selected from the group consisting of alkyl, aryl, carbocyclic aryl polycyclic aryl, heteroaryl, aryloxy, arylalkyl, carbonyl, ester, carboxyl, ether, thioester, thioether, and a tertiary amine;
L 1 is a covalent bond or a multivalent linking group;
M is a substituted or unsubstituted divalent aromatic or polyaromatic radical group, or a substituted or unsubstituted divalent heteroaromatic radical group;
R 2 -R 5 are identical or different and each is independently selected from the group consisting of unsubstituted or substituted alkyl, unsubstituted or substituted alkyloxy, unsubstituted or substituted aryl, unsubstituted or substituted aryloxy, alkylthio, arylthiol, substituted alkyl amino, and substituted aryl amino;
R 6 -R 8 are identical or different and each is independently selected from the group consisting of hydrogen, deuterium, cyano, halo, methyl, vinyl, allyl, and isoprene;
K 2 is a polymerizable functional group; and
x and y are the same or different and are an integer from 1-5, wherein when L 1 is a covalent bond, y=1.
2. The photosensitive composition of claim 1 , wherein the photoinitiator is selected from the group consisting of
and combinations thereof,
where R 1 is CO 2 Ph, CO 2 Me or CO 2 Et; R 2 is ketone, aryl, aryl ether, sulfide aryl ether or alkyl; R 3 is H, OH, COOH, methyl; each of R 4 and R 5 is independently an alkyl group having 1-10 carbon atoms, a cycloalkyl group or a phenyl group; each of R 6 and R 7 is independently an alkyl group having 1-10 carbon atoms, a cycloalkyl group or a phenyl group; R 8 is an alkyl group having 1 to 5 carbon atoms; R 9 is H, methyl or acetyl; R 10 is NO 2 or ArCO; R 11 is an alkyl group of 1 to 6 carbon atoms; and each of R 12 and R 13 is independently an alkyl group having 1-10 carbon atoms, a cycloalkyl group or a phenyl group.
3. A photosensitive composition comprising a photoinitiator, a bismaleimide component, and a thermosetting polymer; wherein the photoinitiator is an oxime ester compound present from 0.5 to 25 percent by weight based on the weight of the bismaleimide component, and wherein the thermosetting polymer is represented by a general Formula (III):
where Ar 1 is heterocycle containing an N, S, O or P atom; R 2 is H, CH 3 , ethyl or t-butyl; R 3 is H, CH 3 , C 1 -C 12 alkyl or C 1 -C 12 alkene; R 4 is cyclobutene, 1-oxy-cyclobutebe, α-methyl cyclobutene; l is an integer of 0 to 10; R 6 is an alkyl group of 1 to 12 carbon atoms, a cycloalkyl group, or an aryl group; n is an integer of 5 to 70; m is an integer of 5 to 50; and o is an integer of 5 to 50; and p is an integer of 5 to 50, wherein l+n+m+o+p=100;
wherein the bismaleimide component comprises a bismaleimide compound or a bismaleimide oligomer.
4. The photosensitive composition of claim 1 , wherein the polymerizable arylcyclobutene monomer is selected from the group consisting of 1-(4-vinyl phenoxy)-benzocyclobutene, 1-(4-vinyl methoxy)-benzocyclobutene, 1-(4-vinyl phenyl)-benzocyclobutene, 1-(4-vinyl hydroxynaphthyl)-benzocyclobutene, 4-vinyl-1-methyl-benzocyclobutene, 4-vinyl-1-methoxy-benzocyclobutene, and 4-vinyl-1-phenoxy-benzocyclobutene.
5. The photosensitive composition of claim 1 , further comprising at least one polymerizable dienophile monomer.
6. The photosensitive composition of claim 5 , wherein the polymerizable dienophile monomer is represented by a general Formula (VII),
where B is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aromatic moiety or substituted or unsubstituted heteroaromatic moiety, hydroxy or substituted or unsubstituted alkyloxy, and R 9 -R 11 are identical or different and each independently is selected from the group consisting of hydrogen, methyl, vinyl, allyl, isoprene, a substituted or unsubstituted alkyl group having 1 to 100 carbon atoms, a halogen, a cyano, a substituted or unsubstituted aryl group having 6 to 100 carbon atoms, a substituted or unsubstituted heteroaryl group having 6 to 100 carbon atoms, and combinations thereof.
7. The photosensitive composition of claim 5 , further comprising at least one polymerizable diene monomer.
8. The photosensitive composition of claim 7 , wherein the polymerizable diene monomer is presented by a general Formula (VIII),
where R 9 is the same or different at each occurrence and is selected from hydrogen and methyl; and
R 10 is the same or different at each occurrence and is selected from hydrogen, C 1-5 alkyl, C 1-5 alkoxy, C 1-5 thioalkyl, and C 5-12 alkenyl.
9. The photosensitive composition of claim 1 , further comprising an inhibitor.
10. The photosensitive composition of claim 9 , wherein the inhibitor is selected from the group consisting of 2,6-di-t-butyl-4-methylphenol, 2,5-di-tert-butyl-1,4-benzohydroquinone, 2-t-butylhydroquinone, 2,3,5-trimethyl-1,4-hydroquinone, 4-methoxyphenol, 2,2,6,6-tetramethyl-1-piperidinyloxy, 4-hydroxy-2,2,6,6-tetramethyl-1-piperidinyloxy, dibenzo-1,4-thiazine, bis(2,4-di-tert-butylphenyl)pentraerythritol diphosphate, triethylene glycol bis[β-(5-tert-butyl-4-hydroxy-3-methylphenyl)propionate], and 2,6-di-tert-butyl-4-octadecylphenol, and combinations thereof.
11. A lithographic process comprising steps of:
(a) image-wise heating a presensitized lithographic printing plate comprising a hydrophilic support and an image-forming layer comprising the photosensitive composition of claim 1 ;
(b) exposing the plate to UV light; and
(c) dissolving and remove a non-imaging area with a solution.
12. The lithographic process of claim 11 , further comprising a step (b1) of heating the plate between the step (b) and (c).
13. The lithographic process of claim 12 , further comprising a step (d) of removing the unheated area of the image-forming layer.
14. The photosensitive composition of claim 1 , wherein the polymerizable nitrogen heterocycle containing monomer comprises a nitrogen heterocycle selected from the group consisting of pyrrole, pyridine, diazines, triazines, imidazoles, benzoimidazoles, and quinolones.
15. The photosensitive composition of claim 3 , wherein the photoinitiator is selected from the group consisting of
and combinations thereof,
where R 1 is CO 2 Ph, CO 2 Me or CO 2 Et; R 2 is ketone, aryl, aryl ether, sulfide aryl ether or alkyl; R 3 is H, OH, COOH, methyl; each of R 4 and R 5 is independently an alkyl group having 1-10 carbon atoms, a cycloalkyl group or a phenyl group; each of R 6 and R 7 is independently an alkyl group having 1-10 carbon atoms, a cycloalkyl group or a phenyl group; R 8 is an alkyl group having 1 to 5 carbon atoms; R 9 is H, methyl or acetyl; R 10 is NO 2 or ArCO; R 11 is an alkyl group of 1 to 6 carbon atoms; and each of R 12 and R 13 is independently an alkyl group having 1-10 carbon atoms, a cycloalkyl group or a phenyl group.
16. The photosensitive composition of claim 3 , wherein the bismaleimide compound is represented by a general formula (I):
where R is substituted or unsubstituted linking group selected from the group consisting of alkylene, alkylenearyl, cycloalkylene, cycloalkylenearyl, cycloalkylalkylene and combinations thereof; and R 1 is selected from the group consisting of hydrogen, deuterium, halogen, cyano, methyl, vinyl, allyl, isoprene, and combinations thereof.
17. The photosensitive composition of claim 3 , wherein the bismaleimide oligomer is represented by a general Formula (II):
where R 2 is H or CH 3 ; R 3 is C 1 -C 40 alkyl, alkyl polydimethyl siloxane, or alkylaryl; R 4 is selected from the group consisting of
and combinations thereof, and n is an integer of 1 to 10.