Abstract: Polymeric materials, methods for making the polymeric materials, and photoresist formulations utilizing the polymeric materials are disclosed. In one aspect, a polymeric material is provided including a condensation product of a reaction mixture comprising an aldehyde with a phenolic monomer composition comprising m-cresol, p-cresol, 3,5-dimethyl phenol, and 2,5-dimethyl phenol. The polymeric material may be further contacted with a photoactive compound and a solvent to form a photoresist formulation.
Abstract: Disclosed are a positive photosensitive resin composition that includes (A) a polybenzoxazole precursor including a first polybenzoxazole precursor including a repeating unit represented by the following Chemical Formula 1 and a repeating unit represented by the following Chemical Formula 2, and having a thermally polymerizable functional group at at least one of the terminal end; (B) a dissolution controlling agent including a novolac resin including a repeating unit represented by the following Chemical Formula 4; (C) a photosensitive diazoquinone compound; (D) a silane compound; (E) an acid generator; and (F) a solvent, a photosensitive resin film prepared using the same, and a semiconductor device including the photosensitive resin film.
Abstract: A positive resist composition comprising a polymer having carboxyl groups substituted with an acid labile group having formula (1) exhibits a high contrast of alkaline dissolution rate before and after exposure, a high resolution, a good pattern profile and minimal edge roughness. In formula (1), A is —(CR22)m—, B is —(CR52)n—, R2 and R5 are hydrogen or alkyl, m and n are 1 or 2, R3 is alkyl, alkenyl, alkynyl or aryl, R6 is alkyl, alkoxy, alkanoyl, alkoxycarbonyl, hydroxyl, nitro, aryl, halogen, or cyano, and p is 0 to 4.
Abstract: A radiation-sensitive composition containing 1 to 80% by weight of a solid component and 20 to 99% by weight of a solvent. The solid component contains a compound B which has (a) a structure derived from a polyphenol compound A by introducing an acid-dissociating group to at least one phenolic hydroxyl group of the polyphenol compound A which is synthesized by a condensation between a di- to tetrafunctional aromatic ketone or aromatic aldehyde each having 5 to 36 carbon atoms with a compound having 1 to 3 phenolic hydroxyl groups and 6 to 15 carbon atoms, and (b) a molecular weight of 400 to 2000. The composition containing the compound B is useful as an acid-amplified, non-polymeric resist material, because it is highly sensitive to radiation such as KrF excimer lasers, extreme ultraviolet rays, electron beams, and X-rays, and provides resist patterns with a high resolution, high heat resistance, and high etching resistance.
Abstract: Provided is an actinic ray-sensitive or radiation-sensitive resin composition including: (A) a resin capable of increasing the solubility in an alkali developer by the action of an acid, the resin containing (a) a repeating unit represented by the following formula (AN-01), (B) a compound capable of generating an acid upon irradiation with an actinic ray or radiation, and (C) a resin that contains at least either a fluorine atom or a silicon atom and contains a repeating unit having a group capable of decomposing by the action of an alkali developer to increase the solubility in an alkali developer: wherein the variables in formula (AN-01) are defined in the description.
Abstract: A sulfonium salt having a 4-fluorophenyl group is introduced as recurring units into a polymer comprising hydroxyphenyl (meth)acrylate units and acid labile group-containing (meth)acrylate units to form a polymer which is useful as a base resin in a resist composition. The resist composition has a high sensitivity, high resolution and minimized LER.
Type:
Grant
Filed:
November 9, 2011
Date of Patent:
July 22, 2014
Assignee:
Shin-Etsu Chemical Co., Ltd.
Inventors:
Youichi Ohsawa, Masaki Ohashi, Seiichiro Tachibana, Jun Hatakeyama
Abstract: A micro-structure is manufactured by patterning a sacrificial film, forming an inorganic material film on the pattern, providing the inorganic material film with an aperture, and etching away the sacrificial film pattern through the aperture to define a space having the contour of the pattern. The patterning stage includes the steps of (A) forming a sacrificial film using a composition comprising a cresol novolac resin and a crosslinker, (B) exposing patternwise the film to first high-energy radiation, (C) developing, and (D) exposing the sacrificial film pattern to second high-energy radiation and heat treating for thereby forming crosslinks within the cresol novolac resin.
Abstract: Disclosed is a photosensitive novolac resin including a structural unit represented by the following Chemical Formula 1 and structural unit represented by the following Chemical Formula 2, wherein R11, R12, R13, and R14 in Chemical Formulae 1 and 2 are the same as defined in the detailed description, a positive photosensitive resin composition including the same, a photosensitive resin film fabricated using the same, and a semiconductor device including the photosensitive resin composition.
Abstract: A negative resist composition including an alkali-soluble resin component (A), an acid generator component (B) that generates acid upon exposure, and a cross-linking component (C), the alkali-soluble resin component (A) including a polymeric compound (F) having a structural unit (f1) containing a base dissociable group and a structural unit (f2) containing a cross-linking group-containing group.
Abstract: Provided are (meth)acrylate monomers containing acetal moieties, polymers containing a unit formed from such a monomer and photoresist compositions containing such a polymer. The monomers, polymers and photoresist compositions are useful in forming photolithographic patterns. Also provided are substrates coated with the photoresist compositions, methods of forming photolithographic patterns and electronic devices. The compositions, methods and coated substrates find particular applicability in the manufacture of semiconductor devices.
Type:
Grant
Filed:
December 31, 2011
Date of Patent:
July 8, 2014
Assignees:
Rohm and Haas Electronics Materials LLC, Dow Global Technologies LLC
Inventors:
Matthias S. Ober, Young Cheol Bae, Yi Liu, Seung-Hyun Lee, Jong Keun Park
Abstract: A polymerizable composition contains a binder polymer containing a functional group having a dipole moment of 3.8 debye or more and being represented by the formula (1), (2), (3), (4) or (5) as defined herein, a radical polymerizable compound and a radical polymerization initiator.
Abstract: A negative-type photosensitive resin composition which is good in sensitivity and resolution, a pattern forming method by the use thereof wherein a pattern which can be developed in an alkali aqueous solution, is excellent in sensitivity, resolution and heat resistance and has a good shape is obtained, and highly reliable electronic parts are provided. The negative-type photosensitive rein composition includes (a) a polymer that has a phenolic hydroxyl group at a terminal and is soluble in the alkali aqueous solution, (b) a compound that generates an acid by irradiating active light, and (c) a compound that can be crosslinked or polymerized by an action of the acid.
Type:
Grant
Filed:
January 13, 2011
Date of Patent:
June 24, 2014
Assignee:
Hitachi Chemical DuPont MicroSystems, Ltd.
Abstract: A pattern is formed by applying a first positive resist composition onto a substrate, heat treatment, exposure, heat treatment and development to form a first resist pattern; causing the first resist pattern to crosslink and cure by irradiation of high-energy radiation of up to 180 nm wavelength or EB; further applying a second positive resist composition onto the substrate, heat treatment, exposure, heat treatment and development to form a second resist pattern. The double patterning process reduces the pitch between patterns to one half.
Type:
Grant
Filed:
August 19, 2008
Date of Patent:
June 3, 2014
Assignee:
Shin-Etsu Chemical Co., Ltd.
Inventors:
Jun Hatakeyama, Takao Yoshihara, Katsuya Takemura, Yoshio Kawai
Abstract: A pattern is formed by coating a first positive resist composition comprising a base resin, a photoacid generator, and a base generator onto a substrate to form a first resist film, patternwise exposure, PEB, and development to form a first resist pattern, heating the first resist pattern for causing the base generator to generate a base for inactivating the pattern to acid, coating a second positive resist composition comprising a C3-C8 alcohol and an optional C6-C12 ether onto the first resist pattern-bearing substrate to form a second resist film, patternwise exposure, PEB, and development to form a second resist pattern.
Type:
Grant
Filed:
May 26, 2010
Date of Patent:
June 3, 2014
Assignee:
Shin-Etsu Chemical Co., Ltd.
Inventors:
Jun Hatakeyama, Kazuhiro Katayama, Youichi Ohsawa, Masaki Ohashi
Abstract: Disclosed are a positive photosensitive resin composition including (A) an alkali soluble resin including a polybenzoxazole precursor, a polyimide precursor, or a combination thereof, (B) a photosensitive diazoquinone compound, (C) a compound represented by the following Chemical Formula 1, and (D) a solvent, and a display device and an organic light emitting device using the same. The Chemical Formula 1 is the same as defined in the detailed description.
Type:
Grant
Filed:
September 5, 2012
Date of Patent:
May 27, 2014
Assignee:
Cheil Industries Inc.
Inventors:
Eun-Kyung Yoon, Eun-Ha Hwang, Jong-Hwa Lee, Ji-Yun Kwon, Dae-Yun Kim, Sang-Kyeon Kim, Sang-Kyun Kim, Sang-Soo Kim, Kun-Bae Noh, Jun-Ho Lee, Jin-Young Lee, Hyun-Yong Cho, Chung-Beom Hong
Abstract: A salt represented by the formula (a): wherein Q1 and Q2 each independently represent a fluorine atom etc., X1 represents a single bond etc., X2 represents a single bond etc., Y1 represents a C3-C6 alicyclic hydrocarbon group etc., with the proviso that —X2—Y1 group has one or more fluorine atoms, and Z+ represents an organic counter cation, and a photoresist composition comprising the salt represented by the formula (a) and a resin comprising a structural unit having an acid-labile group and being insoluble or poorly soluble in an aqueous alkali solution but becoming soluble in an aqueous alkali solution by the action of an acid.
Abstract: A negative photosensitive material is provided which has a lower linear expansion coefficient and a lower hygroscopic expansion coefficient and is excellent in gradational patternability and PI etchability in patterning.
Abstract: A positive photosensitive resin composition includes: (A) a polybenzoxazole precursor; (B) a photosensitive diazoquinone compound; (C) a silane compound; (D) a polyamic acid ester compound; and (E) a solvent. The positive photosensitive resin composition can reduce film shrinkage, can have high sensitivity, high resolution, and excellent residue removal properties, and can provide good pattern shapes.
Abstract: Disclosed are a novel phenol compound comprising a compound represented by Chemical Formula 1, a compound represented by Chemical Formula 2, or a combination thereof, and a positive photosensitive resin composition including the same.
Abstract: There is disclosed a thermosetting silicon-containing antireflection film-forming composition, to form a silicon-containing antireflection film in a multilayer resist process used in a lithography, wherein the composition is at least capable of forming—on an organic film that is an underlayer film having a naphthalene skeleton—a silicon-containing antireflection film whose refractive index “n” and extinction coefficient “k” at 193 nm satisfy the following relationship: 2n?3.08?k?20n?29.4 and 0.01?k?0.5.