Claims
- 1. A light-sensitive composition comprising at least one photosensitive polymeric compound having both photocross-linkable groups capable of undergoing cycloaddition reaction upon exposure to light, and functional groups carrying P--OH bonds, said composition having improved developability with an aqueous alkaline developer,
- wherein the polymeric compound is selected from the group consisting of those compounds prepared by polymerizing low molecular weight compounds each having at least one polymerizable unsaturated bond and at least one photocross-linkable group with low molecular weight compounds each having at least one polymerizable unsaturated bond and at least one functional group carrying P--OH groups where the polymerization occurs in the presence of a polymerization initiator in a proper solvent,
- and further wherein the low molecular weight compounds each having at least one polymerizable unsaturated bond and at least one photocross-linkable group are selected from the group consisting of those represented by the following general formula (II) or (III) ##STR15## wherein R.sup.4 and R.sup.8 each independently represents a hydrogen atom or a methyl group; R.sup.5 and R.sup.9 each independently represents a bivalent coupling group comprising at least two kinds of atoms selected from the group consisting of C, H, N, O and S; R.sup.6 and R.sup.7 each independently represents a hydrogen atom, a halogen atom or an alkyl group provided that they may be bonded together to form a 5- or 6-membered ring; R.sup.10 and R.sup.11 each independently represents H, CN, NO.sub.2, a halogen atom or a C.sub.1 to a C.sub.6 alkyl group; X.sup.2 and X.sup.3 each independently represents a single bond, --COO-- or --CONH--; X.sup.4 represents O or NH; Ar represents an aromatic group which may be substituted or a hetero aromatic group.
- 2. The light-sensitive composition of claim 1 wherein the functional group carrying P--OH bonds is an oxoacid residue of phosphorus atom which may be in the form of a salt with an alkali metal, alkaline earth metal or ammonium ion and is selected from the group consisting of those represented by the following general formula (I): ##STR16## wherein X.sup.1 represents a single bond, oxygen atom, sulfur atom or a group NR.sup.3 ; and R.sup.1, R.sup.2 and R.sup.3 each independently represents a hydrogen atom or a substituted or unsubstituted C.sub.1 to C.sub.20 alkyl, C.sub.3 to C.sub.20 cycloalkyl, C.sub.6 to C.sub.20 aryl or C.sub.7 to C.sub.20 aralkyl group, provided that at least one of R.sup.1 and R.sup.2 represents a hydrogen atom.
- 3. The light-sensitive composition of claim 1 wherein the polymeric compound having both photocross-linkable groups and functional groups carrying P--OH groups is selected from the group consisting of those obtained by introducing photocross-linkable groups and functional groups carrying P--OH groups into polymeric compounds having appropriate functional groups through a polymer reaction.
- 4. The light-sensitive composition of claim 1 wherein in the general formulas (II) and (III), R.sup.4 and R.sup.8 each independently represents a hydrogen atom or a methyl group; R.sup.5 and R.sup.9 each independently represents a bivalent coupling group comprising at least two kinds of atoms selected from the group consisting of C, H, N, O and S; R.sup.6 and R.sup.7 each independently represents a hydrogen atom, a chlorine, bromine or iodine atom or a C.sub.1 to C.sub.4 lower alkyl group, provided that R.sup.6 and R.sup.7 may be bonded together to form a 5- or 6-membered ring; R.sup.10 and R.sup.11 each independently represents H, CN, NO.sub.2, a halogen atom or a C.sub.1 to a C.sub.6 alkyl group; X.sup.2 and X.sup.3 each independently represents a single bond, --COO-- or --CONH--; X.sup.4 represents O or NH; Ar represents a substituted or unsubstituted phenyl group.
- 5. The light-sensitive composition of claim 1 wherein the low molecular weight compound of formula (II) is selected from the group consisting of those represented by the following general formulae: ##STR17## wherein R.sup.4, R.sup.6 and R.sup.7 have the same meanings as those defined above; n.sup.1 to n.sup.9 each independently represents an integer ranging from 1 to 12; and R.sup.12 represents a hydrogen atom or a methyl group.
- 6. The light-sensitive composition of claim 1 wherein the low molecular weight compound of formula (III) is selected from the group consisting of those represented by the following general formulae: ##STR18## wherein R.sup.8, R.sup.10, R.sup.11 and Ar are the same as those defined above; n.sup.10 to n.sup.18 each represents an integer ranging from 1 to 12; and R.sup.13 represents a hydrogen atom or a methyl group.
- 7. The light-sensitive composition of claim 1 wherein the low molecular weight compounds each having at least one polymerizable unsaturated bond and at least one functional group carrying P--OH groups are selected from the group consisting of those represented by the following general formula (IV): ##STR19## wherein m is 1 or 2; R.sup.21 represents a hydrogen atom or a methyl group; R.sup.22 represents a single bond or a coupling group consisting of at least two kinds of atoms selected from the group consisting of C, H, N, O and S, R.sup.22 being a bivalent group when m is equal to 1 or a trivalent group when m equals to 2; Y.sup.1 represents a single bond or a group --COO-- or --CONH--; and Y.sup.2 represents a single bond, O, NH or S.
- 8. The light-sensitive composition of claim 7 wherein the compound represented by the general formula (IV) is selected from the group consisting of those listed below: ##STR20## wherein R.sup.21 is the same as that defined above; and l.sup.1 to l.sup.3 each independently represents an integer ranging from 1 to 12.
- 9. The light-sensitive composition of claim 7 wherein the polymeric compound having photocross-linkable groups and functional groups carrying P--OH groups is a multicomponent copolymer of at least one compound represented by the general formula (II) or (III); at least one compound represented by the general formula (IV) and at least one other polymerizable low molecular weight compound.
- 10. The light-sensitive composition of claim 9 wherein the polymerizable low molecular weight compound is selected from the group consisting of acrylic acid, methacrylic acid, acrylonitrile, methacrylonitrile, acrylates, methacrylates, acrylamides, methacrylamides, allyl compounds, vinyl ethers, vinyl esters, styrenes and crotonic acid esters.
- 11. The light-sensitive composition of claim 1 wherein the polymeric compound have 2 or more photocross-linkable groups on the side chains per molecule on the average; the weight average molecular weight thereof ranges from 2,000 to 300,000; the number average molecular weight thereof ranges from 1,000 to 250,000 and the polydispersity index of the polymeric compound is in the range of from 1.1 to 10.
- 12. The light-sensitive composition of claim 1 further comprising unreacted low molecular weight compounds in an amount of not more than 15% by weight based on the total weight of the polymeric compound.
- 13. The light-sensitive composition of claim 1 wherein the polymeric compound comprises the repeating units of copolymerizable components having photocross-linkable groups in an amount ranging from 30 to 90 mole % and the repeating units of copolymerizable components having functional groups carrying P--OH groups in an amount ranging from 10 to 70 mole %.
- 14. The light-sensitive composition of claim 1 wherein the polymeric compound is selected from the group consisting of those polymerized through ester bonds, amide bonds, urethane bonds, carbonate bonds, imide bonds and any combination thereof.
- 15. The light-sensitive composition of claim 14 wherein the polymeric compound is a polyester selected from those formed by polymerizing, through ester bonds, low molecular weight compounds having both at least one photocross-linkable group and at least two carboxylic acid chlorides moieties, carboxyl groups or carboxylate groups with low molecular weight compounds having at least one functional group carrying P--OH bonds and at least two hydroxyl groups.
- 16. The light-sensitive composition of claim 1 wherein the content of the polymeric compound in the light-sensitive composition ranges from 10 to 99% by weight based on the total weight of the composition.
- 17. The light-sensitive composition of claim 1 wherein it further comprises triplet sensitizers which show a maximum absorption at a wavelength of not less than 300 nm, in an amount ranging from about 1 to about 20% by weight based on the total weight of the light-sensitive composition.
- 18. The light-sensitive composition of claim 1 wherein it further comprises negative working diazo resins, in an amount ranging from 0.1 to 1.5% by weight based on the total weight of the light-sensitive composition.
- 19. The light-sensitive composition of claim 1, wherein said photocross-linkable groups are maleimide groups, cinnamyl groups, cinnamylidene groups or chalcone groups.
Priority Claims (1)
Number |
Date |
Country |
Kind |
1-108290 |
Apr 1989 |
JPX |
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Parent Case Info
This application is a continuation of application Ser. No. 07/514,285, filed Apr. 25, 1990, now abandoned.
US Referenced Citations (13)
Continuations (1)
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Number |
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514285 |
Apr 1990 |
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