Dic Corporation

Dainippon Ink and Chemicals, Incorporated

Tomoyuki Imada

Yusuke Sato

Takakazu Kage

Ichiro Ogura

Nobuya Nakamura

Masanori Miyamoto

Shinya Yamamoto

Norifumi Imaizumi

Dongmi Shin

Seiji Kimoto

Yutaka Kadomoto

Yoshiyuki Takahashi

Hidetomo Kai

Norio Nagae

Shigenobu Kida

Kouji Shiraishi

Masakazu Yoshizawa

To provide a resist material that can form a film with high smoothness and uniformity and has high patterning performance, such as resolution, a resist material is provided that contains a calixarene compound (A) with a molecular structure represented by the following structural formula (1) and a resin component (B); wherein Rdenotes a perfluoroalkyl group or a structural moiety with a perfluoroalkyl group; Rdenotes a hydrogen atom, a polar group, a polymerizable group, or a structural moiety with a polar group or a polymerizable group; Rdenotes a hydrogen atom, an aliphatic hydrocarbon group that optionally has a substituent, or an aryl group that optionally has a substituent; n denotes an integer in the range of 2 to 10; and * denotes a bonding point with an aromatic ring.

Resist material

A calixarene compound represented by formula (1) below is provided. The calixarene compound contains, per molecule, at least one &#x2014;CHOH group or phenolic hydroxy group and at least one carbon-carbon unsaturated bond. R's are a structural moiety (A), which has a &#x2014;CHOH group; a structural moiety (B), which has a carbon-carbon unsaturated bond; a structural moiety (C), which has a &#x2014;CHOH group and a carbon-carbon unsaturated bond; a monovalent organic group (D), which is different from (A), (B), and (C); or a hydrogen atom (E). R's are (A), (B), (C), (D), or (E) provided that not all R's are (E). R's are one of a hydrogen atom, an aliphatic hydrocarbon group, and an aryl group, n is 2 to 10. * is a point of attachment to an aromatic ring. A curable composition including the calixarene compound is provided. A cured product of the curable composition is provided 

Calixarene compound, curable composition, and cured product

The invention provides a novolak resin having excellent properties such as heat resistance, alkali developability, photosensitivity and resolution, a photosensitive composition including the novolak resin, a curable composition including the novolak resin, a cured product thereof, and a resist material which uses the photosensitive composition or the curable composition. The novolak resin is one obtained from a compound (A) having a tris(hydroxyaryl)methine group and an aldehyde compound (B) as essential reaction ingredients. The photosensitive composition includes the novolak resin. The curable composition includes the novolak resin, and the cured product is one obtained from such a composition. The resist material uses the photosensitive composition or the curable composition.

Novolak resins and resist materials

A compound useful as a release agent, and a release agent, a curable composition, and a nanoimprint lithography resin material each containing the compound are provided. More specifically, a calixarene compound with a molecular structure represented by the following structural formula (1) and a composition containing the calixarene compound are provided. wherein Rdenotes a structural moiety with a perfluoroalkyl group, Rdenotes a hydrogen atom, a polar group, a polymerizable group, or a structural moiety with a polar group or a polymerizable group, Rdenotes a hydrogen atom, an aliphatic hydrocarbon group that may have a substituent, or an aryl group that may have a substituent, n denotes an integer in the range of 2 to 10, and * denotes a bonding point with an aromatic ring.

Calixarene compound and curable composition

There are provided a phenolic-hydroxyl-group-containing novolac resin and resist film that are excellent in developability, heat resistance, and conformability to substrates. The phenolic-hydroxyl-group-containing novolac resin is a polycondensate of which the essential reactive components are a phenolic-hydroxyl-group-containing compound (A) represented by Structural Formula (1) [where Ar is a structural part represented by Structural Formula (Ar-1) or (Ar-2), a phenolic-hydroxyl-group-containing compound (B) represented by Structural Formula (2) [where Ris an aliphatic hydrocarbon group having 4 to 20 carbon atoms, and j is an integer from 1 to 3], and an aldehyde compound (C).

Phenolic-hydroxyl-group-containing novolac resin and resist film

Provided are a naphtol-type calixarene compound having high solvent solubility, a method for producing the naphthol-type calixarene compound, a photosensitive composition that contains the naphthol-type calixarene compound and provides a coating having high thermal decomposition resistance, alkali developability, photosensitivity, and resolution, and a resist material and a coating each being made of the photosensitive composition. Specifically, provided is a naphthol-type calixarene compound including a molecular structure represented by general formula (1). [In the formula (1), Rrepresents a hydrogen atom, an alkyl group, an alkoxy group, an optionally substituted aryl group, an optionally substituted aralkyl group, or a halogen atom, and a plurality of Rmay be the same or different from each other; Rrepresents an optionally substituted alkyl group or an optionally substituted aryl group; and n represents an integer of 2 to 10]. 

Naphthol-type calixarene compound and method for producing the same, photosensitive composition, resist material, and coating

Provided are a resin containing phenolic hydroxyl groups having excellent developability, heat resistance, and substrate followability, a photosensitive composition, a curable composition, and a resist film which contain the resin containing phenolic hydroxyl group. The resin containing phenolic hydroxyl groups obtained by reacting a novolac resin intermediate obtained by reacting a triarylmethane compound (A) with an aldehyde compound (B) as essential components, with an alkene compound (C) having 9 to 24 carbon atoms, a photosensitive composition, a curable composition, and a resist film which contain the resin containing phenolic hydroxyl groups.

Resin containing phenolic hydroxyl groups, and resist film

A phenolic hydroxyl-containing compound is provided. The compound dissolves well in solvents and can be formulated into compositions that give coatings superior in thermal decomposition resistance, alkali developability, resolution, and dry-etch resistance. Specifically, the compound is a phenolic hydroxyl-containing calixarene represented by structural formula (1): (where A is a structural unit including a dihydroxynaphthalene- or naphthol-derived structure optionally with a substituent alkyl, alkoxy, aryl, or aralkyl group or halogen atom on the aromatic rings and a methylene group optionally having an alkyl or aryl group in place of one of the hydrogen atoms) and obtained using a dihydroxynaphthalene in combination with a naphthol, with the total repeat number p being an integer of 2 to 10.

Phenolic hydroxyl-containing compound, composition containing the same, and cured film of the composition

A curable composition and a permanent resist film made using this curable composition are provided. The composition dissolves well in solvents, gives coatings superior in alkali developability, thermal decomposition resistance, light sensitivity, and resolution, and is particularly suitable for the formation of permanent resist films. Specifically, the composition is a curable composition for permanent resist films and contains a phenolic hydroxyl-containing compound (A) that has a molecular structure represented by structural formula (1): (where Ris hydrogen, alkyl, or aryl, and n is an integer of 2 to 10; Ris alkyl, alkoxy, aryl, aralkyl, or halogen, and m is an integer of 0 to 4; if m is 2 or more, the plurality of Rs may be the same or different from one another, and may be bonded to either of the two aromatic rings in the naphthylene structure) and a photosensitizer (B1) or curing agent (B2).

Curable composition for permanent resist films, and permanent resist film

The present invention provides a photosensitive composition having excellent heat resistance, low absorbance at the exposure light at wavelengths of g-line, h-line, and i-line, and satisfactory sensitivity even when the thickness of a resist film is increased, and also provides a resist material, a coating film thereof, a novolac phenol resin suitable for these applications, and a method for producing the phenol resin. Specifically, there is provided a novolac phenol resin produced by reacting a phenolic trinuclear compound (A) with formaldehyde under an acid catalyst, the phenolic trinuclear compound (A) including a phenolic trinuclear compound (A1) produced by condensation reaction of dialkyl-substituted phenol with a hydroxyl group-containing aromatic aldehyde and a phenol trinuclear compound (A2) produced by condensation reaction of dialkyl-substituted phenol having alkyl groups at the 2- and 3-positions, 2- and 5-position, the 3- and 4-positions, or 3- and 5-positions with an aromatic aldehyde not having a hydroxyl group, wherein the molar ratio of the phenolic trinuclear compound (A1) to the phenolic trinuclear compound (A2) is 20:80 to 90:10.

Novolac phenol resin, manufacturing method therefor, photosensitive composition, resist material and coating film

A novolac-type phenolic hydroxyl group-containing resin with formula (1) as a structural site repeating unit, Rrepresents one of a hydrogen atom, an alkyl group, and an aryl group, and X represents a structural site (&#x3b1;) represented by formula (2), Rand Reach represent one of a hydrogen atom, an alkyl group, an aryl group, and an aralkyl group; n and m are each an integer of 1 to 3; when n or m is 2 or 3, a plurality of each of Rand Rpresent in a molecule may be the same or different; and Ar represents one of a phenyl group, a naphthyl group, an anthryl group, and a structural site in which one or a plurality of hydrogen atoms in an aromatic nucleus of any one of these groups is substituted by one of an alkyl group, an aryl group, and an aralkyl group). 

Novolac-type phenolic hydroxyl group-containing resin, production method therefor, curable composition, composition for resist, and color resist

The present invention provides a compound containing a modified phenolic hydroxy group, which has a molecular structure represented by General Formula (1) except for a molecular structure represented by the following General Formula (2). In the formulas, Rrepresents a tertiary alkyl group, an alkoxyalkyl group, an aryloxyalkyl group, an acyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a cyclic aliphatic hydrocarbon group containing a hetero atom, or a trialkylsilyl group; Rrepresents a hydrogen atom, an alkyl group, an alkoxy group, an aryl group which may have a substituent, an aralkyl group which may have a substituent, or a halogen atom; and Rrepresents an alkyl group which may have a substituent or an aryl group which may have a substituent.

Compound containing modified phenolic hydroxy group, method for producing compound containing modified phenolic hydroxy group, photosensitive composition, resist material, and resist coating film

Disclosed are a phenolic hydroxyl group-containing resin which has excellent alkali developing properties and makes it possible to exhibit high heat resistance in a cured product obtained therefrom, a production method therefor, a photosensitive composition, a resist material, a coating film, a curable composition and a cured product thereof, and a resist underlayer film. A phenolic hydroxyl group-containing resin, including a compound (A) having a molecular structure represented by the following Structural Formula (1). (In the formula, Rrepresents an alkyl group, an alkoxy group, or an aryl group, Rrepresents a hydrogen atom, an alkyl group, or an aryl group, m is an integer of 1 to 3, and n is an integer of 2 to 15. In the case where m is 2 or more, plural R's may be the same as or different from each other.)

Phenolic hydroxyl group-containing resin, production method therefor, photosensitive composition, resist material, coating film, curable composition and cured product thereof, and resist underlayer film

Provided is a compound containing a phenolic hydroxy group which has excellent heat resistance, a resist composition which has excellent thermal decomposition resistance, optical sensitivity and resolution, and a composition for a resist underlayer coating which has excellent thermal decomposition resistance and dry etching resistance. The compound containing a phenolic hydroxy group has a molecular structure represented by Structural Formula (1) below: wherein Ris a hydrogen atom, an alkyl group or an aryl group, n is an integer of 2 to 10, Ris any one of an alkyl group, an alkoxy group, an aryl group, an aralkyl group and a halogen atom, m is an integer of 0 to 4, and when m is 2 or greater, a plurality of R's may be the same as or different from each other and may be bonded to either one of two aromatic rings of the naphthylene skeleton.

Compound containing phenolic hydroxy group, photosensitive composition, composition for resists, resist coating film, curable composition, composition for resist underlayer films, and resist underlayer film

Provided is a modified hydroxy naphthalene novolak resin which is optimal for a photosensitive composition and a resist material having high optical sensitivity, resolution, and alkali developability, and excellent heat resistance and moisture absorption resistance, and the modified hydroxy naphthalene novolak resin includes a structural moiety (I) represented by Structural Formula as a repeating unit: 

Modified hydroxy naphthalene novolak resin, production method for modified hydroxy naphthalene novolak resin, photosensitive composition, resist material and coating

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Ichihara, Japan

Tomoyuki Imada