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US 2014/0154624 A1Published application
Positive working photosensitive material
AssigneeAz Electronic Materials (Luxembourg) S.A.R.L.
InventorsWeihong LIU, Ping-Hung LU, Medhat TOUKHY, SookMee LAI, Yoshiharu SAKURAI, Aritaka HISHIDA
Life of this patent
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Abstract
Disclosed herein is a photosensitive composition comprising a heterocyclic thiol compound or tautomeric form thereof and its method of use on a substrate, which may include a chalcophile substrate.
Claims20
A positive working photosensitive composition comprising:
- a. at least one photoacid generator;
- b. at least one polymer, comprising one or more (meth)acrylate repeat units and further comprising one or more repeat units with at least one acid cleavable group having formula (5),
- wherein R8-R12 are, independently, —H, F or —CH3, A is a linear or branched C1-C10 allylene group, B is a C1-C12 alkyl or alicyclic group, D is a linking group that may be a chemical bond, a carboxylate group, wherein the carbonyl carbon is bonded to the polymer backbone, or a —COOCH2— group, wherein the carbonyl carbon is bonded to the polymer backbone, Ar is a substituted or unsubstituted aromatic group or heteroaromatic group, E is a linear or branched C2-C10 alkylene group, G is an acid cleavable group, and further where v is 0-10 mole %, w is 0 mole %-20 mole %, x is 14 mole %-80 mole %, y is 0 mole %-40 mole % and z is 20 mole %-50 mole %;
- c. at least one heterocyclic thiol compound comprising a ring structure chosen from the general formulas:
- or tautomers thereof, wherein the ring structure is a single ring structure having 4-8 atoms, or a multi ring structure having 5-20 atoms, and wherein the single ring structure or the multi ring structure is chosen from the group consisting of an aromatic ring, a non aromatic ring, and a heteroaromatic ring, and wherein X is coupled into the ring by a single bond and is chosen from the group consisting of CR1R2, O, S, Se, Te, and NR3, or X is coupled into the ring by a double bond and is chosen from CR1 or N, and Y is chosen from CR1 or N, and wherein R1, R2, and R3 are independently selected from a group consisting of H, a substituted alkyl group having 1-8 carbon atoms, unsubstituted alkyl group having 1-8 carbon atoms, a substituted alkenyl group having 1-8 carbon atoms, unsubstituted alkenyl group having 1-8 carbon atoms, a substituted alkynyl group having 1-8 carbon atoms, unsubstituted alkynyl group having 1-8 carbon atoms, a substituted aromatic group having 1-20 carbon atoms, a substituted heteroaromatic group having 1-20 carbon atoms, unsubstituted aromatic group having 1-20 carbon atoms and unsubstituted heteroaromatic group having 1-20 carbon atoms and further wherein the ring structures of the heterocyclic thiol compound may be unsubstituted or substituted with substituents chosen from the group consisting of saturated hydrocarbon groups, unsaturated hydrocarbon groups, aromatic rings, aliphatic alcohols, aromatic alcohols, heteroaromatic alcohols, amines, amides, imides carboxylic acids, esters, ethers, and halides.
2 more elements
A positive working photosensitive composition comprising:
- a. at least one photoacid generator;
- b. at least one polymer, comprising one or more (meth)acrylate repeat units and further comprising one or more repeat units with at least one acid cleavable group having formula (5),
- wherein R8-R12 are, independently, —H, F or —CH3, A is a linear or branched C1-C10 alkylene group, B is a C1-C12 alkyl or alicyclic group, D is a linking group that may be a chemical bond, a carboxylate group, wherein the carbonyl carbon is bonded to the polymer backbone, or a —COOCH2— group, wherein the carbonyl carbon is bonded to the polymer backbone, Ar is a substituted or unsubstituted aromatic group or heteroaromatic group, E is a linear or branched C2-C10 alkylene group, G is an acid cleavable group, and further where v is 0-10 mole %, w is 0 mole %-20 mole %, x is 14 mole %-80 mole %, y is 0 mole %-40 mole % and z is 20 mole %-50 mole %;
- c. at least one heterocyclic thiol compound chosen from the group consisting of 1H-1,2,4-triazole-3-thiol, 1H-1,2,4-triazole-5-thiol, 1H-benzo[d]imidazole-2-thiol, 1H-imidazole-2-thiol, 1H-imidazole-4-thiol, 1H-imidazole-5-thiol, 2-azabicyclo[2.2.1]hept-2-ene-3-thiol, 2-azabicyclo[3.2.1]oct-2-ene-3-thiol, 2-mercaptopyrimidine-4,6-diol, 3-mercapto-6-methyl-1,2,4-triazin-5-ol, 2-mercaptopyrimidin-4-ol, 2-mercapto-6-methylpyrimidin-4-ol, 1-methyl-1H-imidazole-2-thiol, 1H-indazole-3-thiol, 5-methyl-2-thiouracil, 5,6-dimethyl-2-thiouracil, 6-ethyl-5-methyl-2-thiouracil, 6-methyl-5-n-propyl-2-thiouracil, 5-ethyl-2-thioracil, 5-n-propyl-2-thiouracil, 5-n-butyl-2-thiouracil, 5-n-hexyl-2-thiouracil, 5-n-butyl-6-ethyl-2-thiouracil, 5-hydroxy-2-thiouracil, 5,6-dihydroxy-2-thiouracil, 5-hydroxy-6-n-propyl-2-thiouracil, 5-methoxy-2-thiouracil, 5-n-butoxy-2-thiouracil, 5-methoxy-6-n-propyl-2-thiouracil, 5-bromo-2-thiouracil, 5-chloro-2-thiouracil, 5-fluoro-2-thiouracil, 5-amino-2-thiouracil, 5-amino-6-methyl-2-thiouracil, 5-amino-6-phenyl-2-thiouracil, 5,6-diamino-2-thiouracil, 5-allyl-2-thiouracil, 5-allyl-3-ethyl-2-thiouracil, 5-allyl-6-phenyl-2-thiouracil, 5-benzyl-2-thiouracil, 5-benzyl-6-methyl-2-thiouracil, 5-acetamido-2-thiouracil, 6-methyl-5-nitro-2-thiouracil, 6-amino-2-thiouracil, 6-amino-5-methyl-2-thiouracil, 6-amino-5-n-propyl-2-thiouracil, 6-bromo-2-thiouracil, 6-chloro-2-thiouracil, 6-fluoro-2-thiouracil, 6-bromo-5-methyl-2-thiouracil, 6-hydroxy-2-thiouracil, 6-acetamido-2-thiouracil, 6-n-octyl-2-thiouracil, 6-dodecyl-2-thiouracil, 6-tetradecyl-2-thiouracil, 6-hexadecyl-2-thiouracil, 6-(2-hydroxyethyl)-2-thiouracil, 6-(3-isopropyloctyl)-5-methyl-2-thiouracil, 6-(m-nitrophenyl)-2-thiouracil, 6-(m-nitrophenyl)-5-n-propyl-2-thiouracil, 6-α-naphthyl-2-thiouracil, 6-α-naphthyl-5-t-butyl-2-thiouracil, 6-(p-chlorophenyl)-2-thiouracil, 6-(p-chlorophenyl)-2-ethyl-2-thiouracil, 5-ethyl-6-eicosyl-2-thiouracil, 6-acetamido-5-ethyl-2-thiouracil, 6-eicosyl-5-allyl-2-thiouracil, 5-amino-6-phenyl-2-thiouracil, 5-amino-6-(p-chlorophenyl)-2-thiouracil, 5-methoxy-6-phenyl-2-thiouracil, 5-ethyl-6-(3,3-dimethyloctyl)-2-thiouracil, 6-(2-bromoethyl)-2-thiouracil, tautomers thereof and combinations thereof.
1 more element
Dependencies are inferred from the claim text.