417 results about "Photoacid" patented technology

A photoacid compound having the following general structure:<paragraph lvl="0"><in-line-formula>R-O(CF2)nSO3X< / in-line-formula>wherein n is an integer between about 1 to 4; R is selected from the group consisting of: substituted or unsubstituted C1-C12 linear or branched alkyl or alkenyl, substituted or unsubstituted araalkyl, substituted or unsubstituted aryl, substituted or unsubstituted bicycloalkyl, substituted or unsubstituted tricycloalkyl, hydrogen, alkyl sulfonic acid, substituted or unsubstituted perfluoroalkyl, the general structure F((CF2)pO)m(CF2)q- wherein p is between about 1 to 4, m is between about 0 to 3 and q is between about 1 to 4, and substituted or unsubstituted partially fluorinated alkyl, halofluoroalkyl, perfluoroalkylsulfonic, or glycidyl; and X is selected from the group consisting of: organic cations and covalently bonded organic radicals.

The invention provides various ionic and non-ionic photoacid generator compounds. Photoresist compositions that include the novel ionic and non-ionic photoacid generator compounds are also provided. The invention further provides methods of making and using the photoacid generator compounds and photoresist compositions disclosed herein. The compounds and compositions are useful as photoactive components in chemically amplified resist compositions for various microfabrication applications.

Resist compositions that can be used in immersion lithography without the use of an additional topcoat are disclosed. The resist compositions comprise a photoresist polymer, at least one photoacid generator, a solvent; and a self-topcoating resist additive. A method of forming a patterned material layer on a substrate using the resist composition is also disclosed.

Photoacid generators generate sulfonic acids of formula (1a) or (1b) upon exposure to high-energy radiation.R1—COOCH2CF2SO3−H+  (1a)R1—O—COOCH2CF2SO3−H+  (1b)R1 is a monovalent C20-C50 hydrocarbon group of steroid structure which may contain a heteroatom. The bulky steroid structure ensures adequate control of acid diffusion. The photoacid generators are compatible with resins and suited for use in chemically amplified resist compositions.

The present invention relates to a novel photoresist composition that can be developed with an aqueous alkaline solution, and is capable of being imaged at exposure wavelengths in the deep ultraviolet. The invention also relates to a process for imaging the novel photoresist as well as novel photoacid generators.The novel photoresist comprises a) a polymer containing an acid labile group, and b) a novel mixture of photoactive compounds, where the mixture comprises a lower absorbing compound selected from structure 1 and 2, and a higher absorbing compound selected from structure 4 and 5, where, R1 and R2 R5, R6, R7, R8, and R9 are defined herein; m=1–5; X− is an anion, and Ar is selected from naphthyl, anthracyl, and structure 3, where R30, R31, R32, R33, and R34 are defined herein.

A sulfonic acid onium salt represented by the following formula (1) can be used as a superior radiosensitive acid generator for resist compositions. It is possible to form a good pattern by using a resist composition containing this sulfonic acid onium salt.In formula (1), R1 represents a monovalent organic group, and Q+ represents a sulfonium cation or iodonium cation.

A photoacid compound having the following general structure:R—O(CF2)nSO3X wherein n is an integer between about 1 to 4; R is selected from the group consisting of: substituted or unsubstituted C1-C12 linear or branched alkyl or alkenyl, substituted or unsubstituted araalkyl, substituted or unsubstituted aryl, substituted or unsubstituted bicycloalkyl, substituted or unsubstituted tricycloalkyl, hydrogen, alkyl sulfonic acid, substituted or unsubstituted perfluoroalkyl, the general structure F((CF2)pO)m(CF2)q— wherein p is between about 1 to 4, m is between about 0 to 3 and q is between about 1 to 4, and substituted or unsubstituted partially fluorinated alkyl, halofluoroalkyl, perfluoroalkylsulfonic, or glycidyl; and X is selected from the group consisting of: organic cations and covalently bonded organic radicals.

The present invention relates to photoacid generating compounds, lithographic resists comprising photoacid generating compounds, and to various lithographic processes techniques, and applications. In one embodiment, the present invention provides a photoacid generator of Formula (I):

Photoacid generator salts comprising photoactive cationic moieties and segmented, highly fluorinated-hydrocarbon anionic moieties are disclosed which provide high photoacid strength and can be tailored for solubility and polarity. The present invention further relates to photoacid generators as they are used in photoinitiated acid-catalyzed processes for uses such as photoresists for microlithography and photopolymerization.

An additive polymer comprising recurring units of formula (1) is added to a resist composition comprising a base resin, a photoacid generator, and an organic solvent. R1 is hydrogen or methyl, R2 is alkylene or fluoroalkylene, and R3 is fluoroalkyl. The additive polymer is highly transparent to radiation with wavelength of up to 200 nm. Water repellency, water slip, acid lability, hydrolysis and other properties of the polymer may be adjusted by a choice of polymer structure.

Photoacid generators generate sulfonic acids of formula (1a) upon exposure to high-energy radiation. RC(═O)R1—COOCH(CF3)CF2SO3−H+  (1a) R is hydroxyl, alkyl, aryl, hetero-aryl, alkoxy, aryloxy or hetero-aryloxy, R1 is a divalent organic group which may have a heteroatom (O, N or S) containing substituent, or R1 may form a cyclic structure with R. The photoacid generators are compatible with resins and can control acid diffusion and are thus suited for use in chemically amplified resist compositions.

There is disclosed a liquid ink including a photo acid generating agent that generates an acid upon irradiation with light, a coloring component, and at least one kind of a solvent that is polymerized in the presence of an acid. It is preferable that the amount of the photo acid generating agent contained in the liquid ink falls within a range of between 1 part by weight and 10 parts by weight relative to 100 parts by weight of the solvent, the coloring component consists of a pigment, and the solvent contains at least 50 parts by weight of an acid polymerizable compound, the acid polymerizing compound polymerizing in the presence of the acid, having an alicyclic skeleton and / or an aliphatic skeleton having a viscosity of 50 mPa·s or less and a boiling point of 150° C. or more under room temperature and atmospheric pressure.

The invention relates to a photoimageable antireflective coating composition capable of forming a pattern by development in an aqueous alkaline solution, comprising, (i) a polymer A soluble in a coating solvent and comprises a chromophore, a crosslinking moiety, and optionally a cleavable group which under acid or thermal conditions produces a functionality which aids in the solubility of the polymer in an aqueous alkaline solution and; (ii) at least one photoacid generator; (iii) a crosslinking agent; (iv) optionally, a thermal acid generator; (v) a polymer B which is soluble in an aqueous alkaline solution prior to development, where polymer B is non-miscible with polymer A and soluble in the coating solvent, and; (vi) a coating solvent composition, and (vii) optionally, a quencher. The invention also relates to a process for imaging the antireflective coating.

Sulfonate salts have the formula: R1COOCH2CH2CF2CF2SO3−M+ wherein R1 is alkyl, aryl or hetero-aryl, M+ is a Li, Na, K, ammonium or tetramethylammonium ion. Onium salts, oxime sulfonates and sulfonyloxyimides derived from these salts are effective photoacid generators in chemically amplified resist compositions.

Photoacid generators generate sulfonic acids of formula (1a) or (1c) upon exposure to high-energy radiation.R1—COOCH(CF3)CF2SO3+H+  (1a)R1—O—COOCH(CF3)CF2SO3−H+  (1c)R1 is a C20-C50 hydrocarbon group having a steroid structure. The photoacid generators are compatible with resins and can control acid diffusion and are thus suited for use in chemically amplified resist compositions.

The present invention refers to a photoresist composition comprising (i) a polymer A comprising at least one acid labile group; (ii) at least one photoacid generator; (iii) at least one base; (iv) a polymer B, where polymer B is non-miscible with polymer A and soluble in the coating solvent, and; (v) a coating solvent composition. The present invention also relates to the process of imaging the photoresist.

A photoactive compound is used in combination with a photosensitizer, represented by the following formula (1): A-[(J)m-(X-Pro)]n (1) wherein A represents a hydrophobic unit comprising at least one kind of hydrophobic groups selected from a hydrocarbon group and a heterocyclic group, J represents a connecting group, X-Pro represents a hydrophilic group protected by a protective group Pro which is removable by light exposure, m represents 0 or 1, and n represents an integer of not less than 1. The protective group Pro may be removable by light exposure in association with the photosensitizer (especially, a photo acid generator), or may be a hydrophobic protective group. The hydrophilic group may be a hydroxyl group or a carboxyl group. The photoactive compound has high sensitivity to a light source of short wavelength beams, for resist application, therefore, the photoactive compound is advantageously used for forming a pattern with high resolution.

A chemically amplified positive resist composition contains (A) an organic solvent, (B) a base resin, (C) a photoacid generator, and optionally, (D) a dissolution rate regulator. The base resin (B) is a hydroxystyrene copolymer having different acid labile groups and Mw of 3,000-300,000. The resist composition is highly sensitive to actinic radiation such as deep-UV, electron beam and X-ray, can be developed with aqueous base to form a pattern, and is thus suitable for use in a fine patterning technique.

The present invention discloses a new class of triarylsulfonium salt photoacid generators (PAGs), which are thermally stable and can be activated by long wavelength UV or visible light. The sulfonium PAGs of the present invention are additionally soluble in monomers that can be polymerized by cationic polymerization chemistry, and mixtures of said sulfonium PAGs and monomers can be stored for long periods of time without undergoing polymerization. Furthermore, typical holographic recording media comprising one of these sulfonium PAGs, polymerizable monomer(s), a sensitizing dye, and a binder can be stored for long periods of time without exhibiting significant loss of recording sensitivity. Preferred sulfonium PAGs of the present invention are sulfonium PAGs substituted with one or more fluoro or fluoroalkyl groups.

A photopolymerization initiator comprising (A) a photo acid-generating compound such as diaryliodonium salt (e.g., diphenyl iodonium, bis(p-chlorophenyl)iodonium, etc.), (B) a photo oxidation radical-generating compound such as diarylketone compound, alpha-diketone compound or ketocoumarin compound, and (C) a fused polycyclic aromatic compound such as 1,4-dimethylnaphthalene, 1-methylanthracene, 9-methylanthracene, 9,10-dimethylanthracene or 9,10-diethylanthracene. The photopolymerization initiator makes it possible to efficiently polymerize the cationically polymerizable monomer by the irradiation with visible light.

Disclosed is a fluorinated sulfonic acid salt or fluorinated sulfonic acid group-containing compound having a structure represented by the following general formula (A).In the formula, n indicates an integer of 1 to 10; R indicates a substituted or unsubstituted C1-C20 linear, branched or cyclic alkyl group, a substituted or unsubstituted C1-C20 linear, branched or cyclic alkenyl group, a substituted or unsubstituted C6-C15 aryl group, or a C4-C15 heteroaryl group; and a indicates 1 or 0. A photoacid generator containing the above fluorinated sulfonic acid salt or fluorinated sulfonic acid group-containing compound shows high sensitivity to an ArF excimer laser or the like, presents no concerns about human body accumulation, can generate an acid (photoacid) of sufficiently high acidity, and exhibits high solubility in a resist solvent and good compatibility with a resist resin.

Novel classes of ionic photoacid generator (PAGs) compounds having relatively environmentally friendly anions with no perfluorooctyl sulfonate (no-PFOS) are provided and photoresist composition that comprise such compounds. The new PAGs produce a photoacid having a short or no perfluoro alkyl chain (ie., no-PFOS) attached to a variety of functional groups. The PAGs of the invention are useful as photoactive component in the chemically amplified resist compositions used for microfabrication.

Photoresist additive polymers and photoresist formulations that can be used in immersion lithography without the use of an additional topcoat. The resist compositions include a photoresist polymer, at least one photoacid generator, a solvent; and a photoresist additive polymer. Also a method of forming using photoresist formulations including photoresist additive polymers.

A preferred embodiment of the invention provides a method for forming an integrated circuit. The method comprises forming a resist layer on a substrate. Preferably, the photoresist layer comprises a photo acid generator (PAG). Embodiments include irradiating the resist through a mask to generate a photoacid in the resist, heating the resist at a first temperature, and then heating the resist at a second temperature. Heating at the first temperature evaporates water from the resist. Heating at the second temperature deprotects the resist.

The present invention relates to a photoresist composition comprising a photoacid generator and at least one novel polymer comprising at least one unit as described by structure 1, where, either (i) R1 is an aliphatic cyclic unit of a polymer, R2 is selected from H, F, (C1-C8)alkyl, (C1-C8)fluoroalkyl, cycloalkyl, cyclofluoroalkyl, and (CR3R4)p(CO)OR5, and Rf is selected from F, H, (C1-C8)alkyl, or a fully or partially fluorinated alkyl, and cyclofluoroalkyl, or (ii) R1 and R2 combine to form an aliphatic cyclic unit of a polymer, and Rf is selected from F, H, (C1-C8)alkyl and a fully or partially fluorinated alkyl, and cyclofluoroalkyl, or (ii) R1 and Rf combine to form an aliphatic cyclic unit of a polymer, and R2 is selected from H, F, (C1-C8)alkyl, (C1-C8)fluoroalkyl, cycloalkyl, cyclofluoroalkyl, and (CR3R4)p(CO)OR5; and, R3 and R4 are independently H, F, (C1-C8)alkyl, (C1-C8)fluoroalkyl, cycloalkyl, cyclofluoroalkyl, (CR3R4)p(CO)OR5, R3 and R4 may combine to form an alkylspirocyclic or a fluoroalkylspirocyclic group, X is selected from (C1-C8)alkylene, (C1-C8)fluoroalkylene, O(C1-C8)alkylene, O(C1-C8)fluoroalkylene, cycloalkyl and fluorinatedcycloalkyl, R5 is H or an acid labile group, m=0-1, and p=1-4. The invention also relates to a process for imaging the photoresist composition of the present invention.

Photoacid generators generate sulfonic acids of formula (1a) upon exposure to high-energy radiation.RC(═O)R1—COOCH(CF3)CF2SO3−H+  (1a)R is hydroxyl, alkyl, aryl, hetero-aryl, alkoxy, aryloxy or hetero-aryloxy, R1 is a divalent organic group which may have a heteroatom (O, N or S) containing substituent, or R1 may form a cyclic structure with R. The photoacid generators are compatible with resins and can control acid diffusion and are thus suited for use in chemically amplified resist compositions.

The present invention relates to a photocurable resin composition, wherein the composition comprises:(A) a polyimide resin having one or more primary alcoholic groups with an alcoholic equivalent equal to or less than 3500, said polyimide being soluble in an organic solvent and having a weight average molecular weight of from 5,000 to 500,000; (B) at least one selected from the group consisting of a condensate of an amino compound modified with formalin, optionally further with alcohol, preferably a melamine resin modified with formalin, optionally further with alcohol, and a urea resin with formalin, optionally further with alcohol, and a phenolic compound having, on average, at least two selected from the group consisting of a methylol group and an alkoxy methylol group, and (C) a photoacid generator capable of generating an acid upon irradiation with light of a wavelength of from 240 nm to 500 nm.

An apparatus and method for manufacturing a device using lithography. An underlayer is deposited on a first surface, the underlayer of which is composed of a first resist material adapted to be substantially free of photoacid generators and which includes an acid labile polymer group. A topcoat layer is deposited on top of the underlayer which is composed of a second resist material adapted to be substantially free of acid labile polymer groups and including a photoacid generator. Upon exposure of a portion of the topcoat layer to radiation through to form an exposed region and an unexposed region of a lithographic pattern, photoacid is generated by the topcoat layer and delivered to an interface between the underlayer and the topcoat layer such that the generated photoacid at the exposed region deprotects the acid labile polymer groups at the underlayer top surface to form a deprotected region and a protected region. These two regions cooperate to define an image of the lithographic pattern in the underlayer top surface. The resulting image in the undercoat may then be silylated to form a resistant mask.