Positive type photosensitive resin composition

Claim 2

A positive type photosensitive resin composition comprising a mixture of 100 parts by weight of an alkali- soluble resin and from 5 to 100 parts by weight of at least one 1,2-quinonediazidesulfonic acid ester (I) and/or (II): (I) 1,2-quinonediazidesulfonic acid esters of natural coloring matters selected from the group consisting of c X -pyrone compounds having hydroxyl groups,γ- pyrone compounds having hydroxyl groups, diazine compounds having hydroxyl groups and quinone compounds having hydroxyl groups, and (II) 1,2-quinonediazidesulfonic acid esters of hydroxybenzoate compounds.

Claim 3

A composition according to Claim 1, wherein the alkali-soluble resin is a novolak resin, a hydroxy- styrenic resin, an aminostyrenic resin or a monoolefin- ethylenic unsaturated carboxylic acid copolymer.

Claim 4

A composition according to Claim 1, wherein the alkali-soluble resin is a novolak resin.

Claim 5

A composition according to any one of Claims 1 to 3, wherein the 1,2-quinonediazidesulfonic acid ester (I) is hispidin-1,2-naphthoquinonediazide-5-sulfonic acid diester, hispidin-1,2-naphthoquinonediazide-5-sulfonic acid monoester, 2',3'-dioxy-dibenzo-α-pyrone-1,2-naphthoquinonediazide-5-sulfonic acid diester, ellagic acid-1,2-naphthoquinonediazide-5-sulfonic acid tetraester, ellagic acid-l,2-naphthoquinonediazide-5-sulfonic acid triester, dalbergin-1,2-naphthoquinonediazide-5-sulfonic acid monoester, oospolactone-l,2-naphthoquinonediazide-5-sulfonic acid monoester, eugenin-1,2-naphthoquinonediazide-5-sulfonic acid monoester, brazilin-1,2-naphthoquinonediazide-5-sulfonic acid triester, haematoxylin-1,2-naphthoquinonediazide-5-sulfonic acid pentaester, haematoxylin-1,2-naphthoquinonediazide-5-sulfonic acid tetraester, haematoxylin-l,2-naphthoquinonediazide-5-sulfonic acid triester, haematoxylin-1,2-naphthoquinonediazide-5-sulfonic acid diester, euxanthone-1,2-naphthoquinonediazide-5-sulfonic acid diester, gentimin-1,2-naphthoquinonediazide-5-sulfonic acid diester, chrysin-1,2-naphthoquinonediazide-5-sulfonic acid diester, toringin-l,2-naphthoquinonediazide-5-sulfonic acid diester, primetin-1,2-naphthoquinonediazide-5-sulfonic acid diester, apigenin-1,2-naphthoquinonediazide-5-sulfonic acid triester, apiin-1,2-naphthoquinonediazide-5-sulfonic acid triester, luteolin-1,2-naphthoquinonediazide-5-sulfonic acid triester, quercetin-1,2-naphthoquinonediazide-5-sulfonic acid pentaester, quercetin-1,2-naphthoquinonediazide-5-sulfonic acid tetraester, quercetin-1,2-naphthoquinonediazide-5-sulfonic acid triester, quercetin-1,2-naphthoquinonediazide-5-sulfonic acid diester, quercetin-1,2-naphthoquinonediazide-5-sulfonic acid monoester, quercetin-1,2-naphthoquinonediazide-4-sulfonic acid tetraester, quercetin-1,2-benzoquinonediazide-4-sulfonic acid tetraester, quercitrin-1,2-naphthoquinonediazide-5-sulfonic acid tetraester, isoquercitrin-1,2-naphthoquinonediazide-5-sulfonic acid tetraester, quercimetrin-1,2-naphthoquinonediazide-5-sulfonic acid tetraester, rutin-l,2-naphthoquinonediazide-5-sulfonic acid diester, hyperin-l,2-naphthoquinonediazide-5-sulfonic acid tetraester, galangin-1,2-naphthoquinonediazide-5-sulfonic acid triester, kaempferol-1,2-naphthoquinonediazide-5-sulfonic acid triester, fisetin-1,2-naphthoquinonediazide-5-sulfonic acid triester, morin-1,2-naphthoquinonediazide-5-sulfonic acid tetraester, morin-1,2-naphthoquinonediazide-5-sulfonic acid pentaester, rhamnetin-1,2-naphthoquinonediazide-5-sulfonic acid triester, myricetin- l,2-naphthoquinonediazide-5-sulfonic acid pentaester, naringenin-1,2-naphthoquinonediazide-5-sulfonic acid triester, naringin-1,2-naphthoquinonediazide-5-sulfonic acid diester, sakuranetin-1,2-naphthoquinonediazide-5-sulfonic acid diester, hesperetin-1,2-naphthoquinonediazide-5-sulfonic acid diester, alpinon-1,2-naphthoquinonediazide-5-sulfonic acid diester, catechin-1,2-naphthoquinonediazide-5-sulfonic acid tetraester, daizein-1,2-naphthoquinonediazide-5-sulfonic acid monoester, prunetin-1,2-naphthoquinonediazide-5-sulfonic acid diester, prunitrin-1,2-naphthoquinonediazide-5-sulfonic acid diester, irigenin-l,2-naphthoquinonediazide-5-sulfonic acid diester, iridin-l,2-naphthoquinonediazide-5-sulfonic acid diester, osajin-l,2-naphthoquinonediazide-5-sulfonic acid diester, pelargonidin-1,2-naphthoquinonediazide-5-sulfonic acid triester, cyanidin-1,2-naphthoquinonediazide-5-sulfonic acid tetraester, leucodelphinidin-l,2-naphthoquinonediazide-5-sulfonic acid pentaester, xanthopterin-1,2-naphtoquinonediazide-5-sulfonic acid diester, leucopterin-l,2-naphthoquinonediazide-5-sulfonic acid triester, entropterin-1,2-naphthoquinonediazide-5-sulfonic acid triester, chrysopterin-1,2-naphthoquinonediazide-5-sulfonic acid diester, iodinin-1,2-naphthoquinonediazide-5-sulfonic acid diester, polyporic acid-l,2-naphthoquinonediazide-5-sulfonic acid diester, atromentin-1,2-naphthaquinonediazide-5-sulfonic acid triester, leucomelon-1,2-naphthoquinonediazide-5-sulfonic acid triester, muscarufin-1,2-naphthoquinonediazide-5-sulfonic acid diester, oosporein-1,2-naphthoquinonediazide-5-sulfonic acid triester, juglone-1,2-naphthoquinonediazide-5-sulfonic acid monoester, echinochrome A-1,2-naphthoquinonediazide-5-sulfonic acid tetraester, spinone A-1,2-naphthoquinonediazide-5-sulfonic acid tetraester, spinochrome N-1,2-naphthoquinonediazide-5-sulfonic acid triester, alizarin-1,2-naphthoquinonediazide-5-sulfonic acid diester, purpurin- l,2-naphthoquinonediazide-5-sulfonic acid diester, emodin-1,2-naphthoquinonediazide-5-sulfonic acid diester, carminic acid-1,2-raphthoquinonediazide-5-sulfonic acid triester, kermesic acid-1,2-naphthoquinonediazide-5-sulfonic acid triester, skyrin-1,2-naphthoquinonediazide-5-sulfonic acid hexaester, or pyromycin-1,2-naphthoquinonediazide-5-sulfonic acid triester.

Claim 6

A composition according to any one of Claims 1 to 3, wherein the 1,2-quinonediazidesulfonic acid ester (I) is a 1,2-quinonediazidesulfonic acid ester of a γ-pyrone compound having hydroxyl groups.

Claim 7

A composition according to any one of Claims 1 to 3, wherein the 1,2-quinonediazidesulfonic acid esters of hydroxybenzoate compounds are the compounds represented by the formula (A) and/or (B): wherein a, b and c, which may be the same or different, each represents 1, 2. 3 or 4, ℓ, m and n, which may be the same or different, each represents 0, 1, 2 or 3, (a-ℓ), (b-m) and (c-n) are integers of 1 or more, R 1 , R and R 5 , which may be the same or different, each represents a 1,2-naphthoquinonediazide-4-sulfonyl group, 1,2-naphthoquinonediazide-5-sulfonyl group or 1,2-benzoquinonediazide-4-sulfonyl group, R , R and R , which may be the same or different, each represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aroxy group, an aralkoxy group, a cyano group or a nitro group, R 7 represents an alkyl group, an aryl group or an aralkyl group, and Z is an oxalkylene or alkylene group represented by the formula: C p H 2p )0] C p H 2p - (wherein p is 1, 2, 3 or 4, and r is 0 or an integer of 1 to 100).

Claim 8

A composition according to Claim 6, wherein the compound represented by formula (A) is ethylene glycol di(2-hydroxybenzoate)-1,2-naphthoquinonediazide-4-sulfonic acid diester, ethylene glycol di(3-hydroxybenzoate)-1,2-naphthoquinonediazide-5-sulfonic acid diester, ethylene glycol di(4-hydroxybenzoate)-l,2-benzoquinonediazide-4-sulfonic acid diester, ethylene glycol di(4-hydroxybenzoate) -1, 2 -naphthoquinonediazide-5-sulfonic acid diester, ethylene glycol di(2,3-dihydroxybenzoate)-1,2-naphthoquinonediazide-5-sulfonic acid tetraester, ethylene glycol di(2,6-dihydroxybenzoate)-1,2-naphthoquinonediazide-5-sulfonic acid triester, ethylene glycol di(3,5-dihydroxybenzoate)-1,2-naphthoquinonediazide-5-sulfonic acid diester, ethylene glycol di(3,4,5-tri- hydroxybenzoate)-1,2-naphthoquinonediazide-5-sulfonic acid hexaester, ethylene glycol (2-nitro-3,4,5-tri- hydroxybenzoate)-1,2-naphthoquinonediazide-5-sulfonic acid hexaester, ethylene glycol (2-cyano-3,4,5-tri- hydroxybenzoate)-1,2-naphthoquinonediazide-5-sulfonic acid hexaester, ethylene glycol di(3,4,5-trihydroxy- benzoate)-1,2-naphthoquinonediazide-5-sulfonic acid pentaester, ethylene glycol di(3,4,5-trihydroxybenzoate)-1,2-naphthoquinonediazide-5-sulfonic acid tetraester, ethylene glycol di(3,4,5-trihydroxybenzoate)-1,2-naphthoquinonediazide-5-sulfonic acid triester, ethylene glycol di(3,4,5-trihydroxybenzoate)-1,2-naphthoquinonediazide-5-sulfonic acid diester, ethylene glycol di(3,4,5-trihydroxybenzoate)-1,2-naphthoquinonediazide-5-sulfonic acid monoester, ethylene glycol di(2,4,6-trihydroxy- benzoate)-1,2-naphthoquinonediazide-5-sulfonic acid pentaester, diethylene glycol di(2,3-dihydroxybenzoate)-1,2-naphthoquinonediazide-5-sulfonic acid diester, diethylene glycol di(2-hydroxy-3-methylbenzoate)-1,2-naphthoquinonediazide-5-sulfonic acid diester, triethylene glycol di(3-hydroxy-4-methylbenzoate)-1,2-naphthoquinonediazide-5-sulfonic acid diester, tetraethylene glycol di(4-chloro-2-hydroxybenzoate)-1,2-naphthoquinonediazide-5-sulfonic acid diester, polyethylene glycol di(5-chloro-2-hydroxybenzoate)-1,2-naphthoquinonediazide-5-sulfonic acid diester, propylene glycol di(3-chloro-4-hydroxybenzoate)-1,2-naphthoquinonediazide-5-sulfonic acid diester, polypropyelne glycol di(3-hydroxy-4-nitrobenzoate)-l,2-naphthoquinonediazide-5-sulfonic acid diester, polypropylene glycol di(2-hydroxy-5-methoxybenzoate)-1,2-naphthoquinonediazide-5-sulfonic acid diester, 1,3-propanediol di(4-hydroxy-3-methoxybenzoate)-1,2-naphthoquinonediazide-5-sulfonic acid diester, 1,3-propanediol di(3,4,5-trihydroxybenzoate)-1,2-naphthoquinonediazide-5-sulfonic acid pentaester, 1,4-butanediol di(3-hydroxybenzoate)-l,2-naphthoquinonediazide-5-sulfonic acid diester, tetramethylene glycol di(5-bromo-2-hydroxybenzoate)-1,2-naphthoquinonediazide-5-sulfonic acid diester, polytetrahydrofuran glycol di(3,4,5-trihydroxybenzoate)-1,2-naphthoquinonediazide-5-sulfonic acid pentaester, or neopentyl glycol di(3,4,5-trihydroxybenzoate)-1,2-naphthoquinonediazide-5-sulfonic acid pentaester.

Claim 9

A composition according to Claim 6, wherein the compound represented by formula (B) is ethylene glycol monomethyl-mono(3,4,S-trihydroxybenzoate)-1,2-naphthoquinonediazide-5-sulfonic acid triester, ethylene glycol monoethyl-mono(3,4,5-trihydroxybenzoate)-1,2-naphthoquinonediazide-5-sulfcnic acid triester, ethylene glycol monoethyl-mono(2,4,6-trihydroxybenzoate)-1,2-naphthoquinonediazide-5-sulfonic acid triester, diethylene glycol monoethyl-mono(2,3-dihydroxybenzoate)-1,2-naphthoquinonediazide-5-sulfonic acid diester, triethylene glycol monoethyl-mono(3,5-dihydroxybenzoate)-1,2-naphthoquinonediazide-5-sulfonic acid diester, or ethylene glycol monophenyl-mono(3,4,5-trihydroxybenzoate)-l,2-naphthoquinonediazide-5-sulfonic acid triester.

Claim 10

A composition according to any one of Claims 1 to 8, wherein the amount of the 1,2-quinonediazidesulfonic acid ester is from 10 to 50 parts by weight.

Claim 11

A composition according to any one of Claims 1 to 9, which further comprises a condensation reaction product of a compound represented by the formula (E): wherein n is 1, 2 or 3, and R is an alkyl group, an aryl group or an aralkyl group, with 1,2-naphthoquinonediazide-4-sulfonyl chloride, 1,2-naphtoquinonediazide-5-sulfonyl chloride or 1,2-naphthoquinonediazide-4-sulfonyl chloride in an amount of not more than 100 parts by weight per 100 parts by weight of the alkali-soluble resin.