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公开(公告)号：JPS6429837A
公开(公告)日：1989-01-31
申请号：JP18537387
申请日：1987-07-27
Applicant: TOSOH CORP
Inventor： MATSUMURA KOUZABUROU , KIYOTA TORU , NAKAZAWA TSUNEKO , TSUTSUMI YOSHITAKA
IPC: G03F7/039 , H01L21/027
Abstract: PURPOSE:To improve the sensitivity and the resolution and the dry-etching durability of a resist material by using a polymer having a specified repeating unit as the resist material. CONSTITUTION:The resist material comprises the polymer having the repeating unit shown by the formula wherein X is halogen atom, R is hydrogen atom or a lower alkyl group, (n) is an integer of 20-20,000. The polymer is obtd. by homopolymerizing an alpha-halogen substd. acrylic acid ester, and the halogen atom substd. at alpha-position of said ester is preferably fluorine, chlorine or bromine atom, and the substituent group of a benzene ring is hydrogen atom or a lower alkyl group, and the lower alkyl group is preferably 1-5C alkyl group. Thus, the resist material having the high sensitivity and resolution and the excellent dye-etching durability is obtd.
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公开(公告)号：JPS63234006A
公开(公告)日：1988-09-29
申请号：JP30770186
申请日：1986-12-25
Applicant: TOSOH CORP
Inventor： TSUTSUMI YOSHITAKA , KIYOTA TORU , AKEYAMA HIDEO , MATSUMURA KOUZABUROU , NAKAZAWA TSUNEKO
Abstract: PURPOSE:To provide the titled novel ester derivative containing halogen and benzene ring, easy to cause main chain degradation reaction by electron beam or X-ray irradiation, useful as a resist material improved in dry-etching resistance. CONSTITUTION:The objective novel ester derivative of formula I [A is constituent derived from a monomer having copolymerizable double bond; R is group of formula II or III (R1 and R2 are each H or fluorine-substituted methyl; but not H simultaneously; R3 is H or lower alkyl); X is halogen or CH3; m is positive integer; n is 0 or positive integer, n/m being 0-2]. This ester derivative can be prepared by polymerization, e.g., of the corresponding acrylic ester monomer (e.g., alpha-chloroacrylic acid 1-phenyl-2,2,2-trifluoroethyl ester).
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公开(公告)号：JPS6374054A
公开(公告)日：1988-04-04
申请号：JP21793186
申请日：1986-09-18
Applicant: TOSOH CORP
Inventor： TSUTSUMI YOSHITAKA , KIYOTA TORU , MATSUMURA KOUZABUROU , NAKAZAWA TSUNEKO
Abstract: PURPOSE:To improve definition in a developing stage for a specific resist mate rial by using a solvent mixture composed of diisobutyl ketone and aliphat. satd. alcohol specified in carbon atoms as a liquid developer. CONSTITUTION:The resist material is an acrylate polymer contg. halogen in the alpha-position, the repeating unit of which is expressed by formula I, and fluo rine and benzene ring in the ester part and is obtd. by polymerizing a monomer. In formula I, X denotes fluorine, chlorine, R1, R2 denote hydrogen, fluorine substd. methyl group (where R1, R2 do not simultaneously take hydrogen), R3 denotes hydrogen, alkyl group of 1-5C, (n) denotes an integer in the sange of 20-20,000. This polymer is dissolved and a uniform film is formed. Develop ment is executed by using the solvent mixture composed of the diisobutyl ketone and the aliphat. satd. alcohol of 1-6C. the definition is thereby improved.
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公开(公告)号：JPS62241906A
公开(公告)日：1987-10-22
申请号：JP8417386
申请日：1986-04-14
Applicant: TOSOH CORP
Inventor： MATSUMURA KOUZABUROU , KIYOTA TORU , AKEYAMA HIDEO , TSUTSUMI YOSHITAKA , NAKAZAWA KEIKO
IPC: C08F20/22
Abstract: PURPOSE:To obtain the titled polymer excellent in dry-etching resistance and useful as a resist material, a water repellent, a stainproof agent or a resin modifier, comprising units each containing a trifluoromethyl group in the alphaposition and a benzene ring in the ester moiety. CONSTITUTION:Potassium alpha-trifluoromethylacrylate is reacted with an alpha- substituted benzyl bromide to obtain an alpha-trifluoromethyl acrylate monomer (e.g., benzyl alpha-trifluoromethylacrylate). This monomer is polymerized at -80-100 deg.C in an organic solvent (e.g., toluene) in the presence of a catalyst (e.g., t-butoxypotassium) to obtain the titled polymer having repeating units each of which has a trifluoromethyl group in the alpha position and a benzene ring in the ester moiety and represented by the formula (wherein R are each H or a lower alkyl and n is 20-20,000).
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公开(公告)号：JPH01216345A
公开(公告)日：1989-08-30
申请号：JP4065188
申请日：1988-02-25
Applicant: TOSOH CORP
Inventor： MATSUMURA KOUZABUROU , KIYOTA TORU , YAMAMOTO TAKASHI , NAGAOKA KEIKO
Abstract: PURPOSE:To improve the sensitivity and the resolution of the title composition by incorporating a polyamidic acid ester having a specified repeating unit, a polymer contg. azido group and optionally, a sensitizing agent in the title composition. CONSTITUTION:The title composition incorporates 100pts.wt. of the polyamidic acid ester having the repeating unit shown by formula I, 1-100pts.wt. of the polymer contg. the azido group and optionally, the sensitizing agent. In formula I, R1 is a four valent org. group capable of forming a carbon aromatic ring group or a heterocyclic ring group, R2 is a two valent contg. one or more of carbon aromatic ring groups and/or heterocyclic ring groups in one molecular structure, R3 is a group having a carbon-carbon double bond capable of crosslinking with active rays, etc. Thus, the photosensitive resin composition capable of forming a relief-pattern having the high sensitivity and the excellent definition is obtd.
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Patent Agency Ranking
公开(公告)号：JPH01216344A
公开(公告)日：1989-08-30
申请号：JP4064988
申请日：1988-02-25
Applicant: TOSOH CORP
Inventor： MATSUMURA KOUZABUROU , KIYOTA TORU , YAMAMOTO TAKASHI , NAGAOKA KEIKO
Abstract: PURPOSE:To obtain a photosensitive polymer composition with high sensitivity and good resolution by incorporating a polymer having a specified repeating unit as a main component, an aromatic bisazide compd. and optionally a sensitizing agent and a compd. capable of polymerizing with light, in the title composition. CONSTITUTION:100pts.wt. of the polymer contg. a repeating unit shown by formula I as the main component, 0.1-100pts.wt. of the aromatic bisazide compd. shown by formula II, and optionally, the sensitizing agent and the compd. having an ethylenic unsatd. binding and capable of polymerizing with the light are incorporated in the composition. In formulas I and II, R1 and R2 are each a carbon ring group or a heterocyclic ring group, R3 is a group contg. a cross- linkable azide compd., R4 is hydrogen atom or a lower alkyl group, etc. Thus, the photosensitive polymer composition with high sensitivity and good resolution is obtd.
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公开(公告)号：JPH01216343A
公开(公告)日：1989-08-30
申请号：JP4065088
申请日：1988-02-25
Applicant: TOSOH CORP
Inventor： MATSUMURA KOUZABUROU , KIYOTA TORU , YAMAMOTO TAKASHI , NAGAOKA KEIKO
Abstract: PURPOSE:To obtain a photosensitive polymer composition with high sensitivity and good resolution by incorporating a polymer having a specified repeating unit as a main component, a photoinitiator having the high sensitivity against energy rays and optionally, a sensitizing agent and a compd. capable of polymerizing with light in the title material. CONSTITUTION:100pts.wt. of the polymer having the repeating unit shown by formula I as the main component, 0.1-100pts.wt. of the photoinitiator having the high sensitivity against the energy rays, and optionally, the sensitizing agent and the compd. having an ethylenic unsatd. binding and capable of polymerizing with the light are incorporated in the composition. In formula I, R1 and R2 are a carbon ring group or a heterocyclic ring group, R3 is a group contg. a crosslinkable azide compd. Thus, the photosensitive polymer composition with high sensitivity and good resolution is obtd.
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公开(公告)号：JPH01173026A
公开(公告)日：1989-07-07
申请号：JP33490387
申请日：1987-12-28
Applicant: TOSOH CORP
Inventor： MATSUMURA KOUZABUROU , KIYOTA TORU , YAMAMOTO TAKASHI , NAGAOKA KIYOUKO
Abstract: PURPOSE:To increase the difference in solubility between an exposed part and unexposed part and to obtain a compsn. having high resolution by constituting the compsn. of a heat resistant photosensitive material of a polymer essentially consisting of a prescribed repeating unit, a specific arom. bisazide compd. and a polymer compsn. of a diene monomer contg. carbon double bonds. CONSTITUTION:The compsn. of the heat resistant photosensitive material is constituted of 100pts.wt. polymer essentially consisting of the repeating unit expressed by formula I, 0.1-100pts.wt. arom. bisazide compd. expressed by formula II and the polymer compsn. obtd. by polymerizing the diene monomer contg. the carbon-carbon double bonds expressed by formula III and by adding a sensitizer at need thereto. The high definition is obtd. and the high sensitivity is attained by increasing the difference in the solubility between the exposed part and the unexposed part. In formula, R1, R2 are carbon cyclic group, heterocyclic group; R3 is a crosslinkable ethylenic double bond group; R4 is hydrogen, lower alkyl group, -OH, etc.; (n) is 0 or 1; R7 is a hydrogen atom, alkyl group or alkoxy group of 1-4C.
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公开(公告)号：JPS6449039A
公开(公告)日：1989-02-23
申请号：JP20515587
申请日：1987-08-20
Applicant: TOSOH CORP
Inventor： TSUTSUMI YOSHITAKA , KIYOTA TORU , MATSUMURA KOUZABUROU , NAGAOKA TSUNEKO , YANAGIHARA TOSHIMITSU
IPC: G03F7/039
Abstract: PURPOSE:To improve the dry etching durability of the titled pattern by using a specified halogen contg. polyacrylic acid ester derivative for a resist material. CONSTITUTION:The halogen contg. polyacrylic acid ester derivative shown by formula I is used for the resist material. In the formula, A is a constituting unit derived from a monomer having a copolymerizable double bond, X is a halogen atom or methyl group, (m) is a positive integer, (n) is 0 or a positive integer, (n/m) is 0-2, (m+n) is 20-20,000, Y1-Y5 are each fluorine or hydrogen atom, and at least one of the groups Y1-Y5 is fluorine atom. As the halogen contg. polyacrylic acid ester derivative, especially, the alpha-halogen derivative thereof contains a halogen atom at the alpha-position and at the ester part of said derivative, said derivative is liable to cause a disintegration reaction. As the result, the sensitivity of the titled pattern is improved. And, as the deviation contains a benzene ring, the dry-etching durability of the titled pattern is improved.
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公开(公告)号：JPS62240956A
公开(公告)日：1987-10-21
申请号：JP30770286
申请日：1986-12-25
Applicant: TOSOH CORP
Inventor： TSUTSUMI YOSHITAKA , KIYOTA TORU , AKEYAMA HIDEO , MATSUMURA KOUZABUROU , NAKAZAWA KEIKO
Abstract: PURPOSE:To enhance sensitivity and resolution to electron beams and X-rays by using a polymer composed of specified repeating units as a resist material. CONSTITUTION:The polymer to be used as the resist is composed of the repeating units represented by formula I in which R1 is methyl, fluorinated methyl, or the like; R2 is 3,5-difluorophenyl or the like; each of R3 and R4 is H, alkyl, or the like; and R5 is optionally fluorinated phenyl. This polymer is obtained by homopolymerizing alpha-substituted acrylate represented by formula II, which is obtain by reacting an alpha-substituted acrylic acid with a chlorinating agent, such as thionyl chloride, phosphorus pentachloride, or oxalyl chloride to synthesize the alpha-substituted acryloyl chloride, and further reacting it with alcohol having a benzene ring and containing an fluorine atom in the presence of a base, thus permitting the obtained resist material to be enhance in sensitivity and resolution to electron beams and X-ray, and superior in dry etching resistance.
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