Sumitomo Chemical Company, Limited

Hiroshi Moriuma

Yasunori Uetani

Haruyoshi Osaki

Yoshiyuki Takata

Kyoko Nagase

Kazuhiko Hashimoto

Takeshi Hioki

Satoshi Yamaguchi

Hirotoshi Nakanishi

Jun Tomioka

Akira Kamabuchi

Isao Yahagi

Yasunori Doi

Chinehito Ebina

Katsuhiko Namba

Seiko Kurio

Kaoru Tatekawa

Kenji Ohashi

The present invention provides a sulfonate of the formula (I'): wherein Q, Q, Q, Qand Qeach independently represent hydrogen, alkyl having 1 to 16 carbon atoms, alkoxy having 1 to 16 carbon atoms, or electron attractive group, with the proviso that at least one of Q, Q, Q, Qand Qrepresents alkyl having 3 to 16 carbon atoms or alkoxy having 3 to 16 carbon atoms, and at least one of Q, Q, Q, Qand Qis electron attractive group; and The present invention also provides a chemical amplification type positive resist composition comprising a sulfonate of the formula (I) wherein Arepresents counter ion, and Q, Q, Q, Qand Qare as defined above; and

Amplification type positive resist composition

The present invention provides a sulfonate of the formula (I):wherein Q, Q, Q, Qand Qeach independently represent hydrogen, alkyl having 1 to 16 carbon atoms, alkoxy having 1 to 16 carbon atoms, halogen, aryl having 6 to 12 carbon atoms, aralkyl having 7 to 12 carbon atoms, cyano, sulfide, hydroxy, nitro or a group of the formula (I')&#x2014;COO&#x2014;X&#x2014;Cy&#x2003;&#x2003;(I&#x2032;)wherein X represents alkylene and at least one &#x2014;CH&#x2014; in the alkylene may be substituted by &#x2014;O&#x2014; or &#x2014;S&#x2014;, and Cyrepresents alicyclic hydrocarbon having 3 to 20 carbon atoms,and Arepresents a counter ion, with the proviso that at least one of Q, Q, Q, Qand Qis the group of the formula (I&#x2032;). The present invention also provides a chemical amplification type positive resist composition comprising a sulfonate of the formula (I) and resin which contains a structural unit having an acid labile group and which itself is insoluble or poorly soluble in an alkali aqueous solution but becomes soluble in an alkali aqueous solution by the action of an acid.

Sulfonate and resist composition

A resist composition excellent in balance of performance of resolution and sensitivity as well as in solubility and, particularly, suitable for use as a positive photo resist which comprises a resin having a alicyclic lactone structure unit that is insoluble in alkali by itself but becomes soluble due to the action of an acid, a solvent containing 2-heptanone and an acid generating agent, wherein a content of 2-heptanone in the solvent is in a weight ratio of from about 5 to about 95% is provided.

Chemical amplifying type positive resist composition

Positive resist composition

Chemically amplifying type positive resist composition

The object of the present invention is to provide resin composition for intermediate layer of a three-layer resist comprising (A) a polyorganosilsesquioxane resin having a weight-average molecular weight of from 1000 to 50000 and having two or more functional groups, which polymerize or condense at the presence of a acid, in the molecule, and (B) a compound generating an acid by electromagnetic wave or heat, and resin composition for intermediate layer of a three-layer resist, comprising (C) a polyorganosilsesquioxane resin having in the molecule a hydroxyl group and having a weight-average molecular weight of from 1000 to 50000, as resin composition for intermediate layer of a three-layer resist which, when ketone compounds, aromatic compounds and the like are used as a resist solvent, does not cause dissolution of an intermediate layer in applying an upper layer resist and does not cause formation of a mixing layer at the interface with the upper layer resist, and which shows little change by time, excellent in storage stability, and can form a hardened film without cracking.

Resin composition for intermediate layer of three-layer resist

A positive resist composition excellent in resolution, having a good balance with other performances required to resists and comprising an alkali-soluble resin, a radiation-sensitive ingredient and a hydroxyphenyl ketone compound represented by the following formula (I):

Positive resist compositions comprising a hydroxyphenyl ketone

A non-chemically enhanced type positive resist composition includes an alkali-soluble novolak resin, a quinonediazide type sensitizer and at least one of the following compounds (a) and (b):

A positive-working resist composition comprising (A) a quinonediazide compound, (B) an alkali-soluble resin, and (C) a solvent system comprising 2-heptanone, ethyl lactate and .gamma.-butylactone in which the quinonediazide compound exhibits a very high solubility and which characteristics such as sensitivity, profile and coatability are excellent.

Positive-working quinonediazide sulfonic acid ester resist composition

A positive resist composition containing a quinone diazide compound and an alkali-soluble resin which contains a resin (A) obtained by a condensation reaction of an aldehyde compound, at least one phenol compound of the formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are independently a hydrogen atom, or a C.sub.1 -C.sub.4 alkyl or alkoxy group, and j is 1 or 2, and at least one compound of the formula: ##STR2## wherein R'.sub.1, R'.sub.2, R'.sub.3, R'.sub.4, R'.sub.5 and R'.sub.6 are independently a hydrogen atom, or a C.sub.1 -C.sub.4 alkyl or alkoxy group, R'.sub.7 is a hydrogen, a C.sub.1 -C.sub.4 alkyl group or an aryl group, and k, m and n are independently 0, 1 or 2 provided that a sum of k, m and n is larger than 2, which composition is excellent in balance among various properties such as a profile, a sensitivity, heat resistance and a depth of focus.

A positive resist composition comprising a quinonediazide compound and an alkali-soluble resin containing resin (A) obtainable through a condensation reaction of at least one compound represented by the general formula (I): ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 independently of one another each represent a hydrogen atom or an alkyl or alkoxy group having 1-4 carbon atoms and k represents 1 or 2, at least one polyphenol compound represented by the general formula (II): ##STR2## wherein R.sub.4 ' to R.sub.6 ' each represent a hydrogen atom or an alkyl or alkoxy group and n represents 1 or 2, with an aldehyde compound. This positive resist composition is excellent in properties such as profile, resolution, heat resistance, etc.

A positive resist composition comprising a quinonediazide compound and an alkali-soluble resin containing resin (A) obtainable through a condensation reaction of at least one compound represented by the general formula (I): ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 independently of one another each represent a hydrogen atom or an alkyl or alkoxy group having 1-4 carbon atoms and k represents 1 or 2, at least one polyphenol compound represented by the general formula ( II ): ##STR2## wherein R.sub.4 ' to R.sub.6 ' each represent a hydrogen atom or an alkyl or alkoxy group and n represents 1 or 2, with an aldehyde compound. This positive resist composition is excellent in properties such as profile, resolution, heat resistance, etc. and nearly completely free from scum

A positive type resist composition comprising an alkali-soluble novolac resin, a quinonediazide compound and a compound represented by general formula (I): ##STR1## wherein Y.sub.1 to Y.sub.10 each represent a hydrogen atom, a hydroxyl group or an alkyl group, provided that at least one of Y.sub.1 to Y.sub.10 is a hydroxyl group, and X represents one of the groups represented by the following formulas: ##STR2## wherein R.sub.1 to R.sub.3 independently of one another each represent a hydrogen atom or an alkyl group, provided that, as measured by GPC, the pattern area of the component having a molecular weight, converted to polystyrene, 1,000 or below in the alkali-soluble novolac resin is 25% or less based on the total pattern area of the novolac resin from which the pattern area of the unreacted phenol compound is excepted. This positive type resist composition is excellent in the balance between performances such as sensitivity, resolution, heat resistance and adhesive property.

Positive type quinonediazide resist composition containing

A positive resist composition containing a 1,2-quinone diazide compound and an alkali-soluble resin which constitutes a resin (I) obtainable through a condensation reaction of a phenol mixture containing m-cresol and 2-tert.-butyl-5-methylphenol with an aldehyde., which has well balanced sensitivity, resolution and heat resistance properties.

Radiation-sensitive positive resist composition comprising an

A positive type resist composition comprising an alkali-soluble resin and a quinonediazide compound, wherein the alkali-soluble resin containing resin (A) is obtainable through a condensation reaction with at least one phenol compound represented by the following general formula (I): ##STR1## wherein R.sub.1 to R.sub.3 independently of one another each represent a hydrogen atom or an alkyl or alkoxy group having 1-4 carbon atoms and k represents 1 or 2, at least one compound represented by the following general formula (II): ##STR2## wherein R.sub.4 represents a hydrogen atom, an alkyl group having 1-4 carbon atoms or a phenyl group, R.sub.5 to R.sub.7 independently of one another each represent a hydrogen atom or an alkyl or alkoxy group having 1-4 carbon atoms and n represents 1 or 2, and an aldehyde compound. This composition is excellent in the balance between performances such as sensitivity, heat resistance and profile, and is free from scum.

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Nara, Japan

Hiroshi Moriuma