Korea Kumho Petrochemical Co., Ltd.

Seong-Ju Kim

Joo-Hyeon Park

Sun-Yi Park

Ji-Hong Kim

Ki-Dae Kim

Dong-Chul Seo

Dae Young Lee

Hosull Lee

Dong-Chui Seo

Dae-Youp Lee

Seong-Geun Jang

Polymer for radiation-sensitive resist and resist composition containing the same

A chemical amplification positive amplification which can be formed into resist patterns much improved in transparency, photosensitivity and resolution and is suitable to KrF and ArF excimer lasers, enabling a submicrolithography process to be as exquisite as 0.2 &mgr;m or less. This composition is based on a copolymer of the formula I, ranging, in polystyrene-reduced weight average molecular weight, from 3,000 to 50,000 with a molecular weight distribution (M,/M,) of 1.0 to 2.0, and a low molecular weight compound of the formula VI:

Chemically amplified positive photoresist composition

A copolymer represented by the formula I and a chemical amplification resist containing the copolymer, which can be easily controlled in sensitivity by regulating the content and kind of the norbornene derivatives in the matrix polymers in addition to being superior in adherence to substrate and dry etch resistance: ##STR1## wherein, X is selected from the group consisting of the following general formulas II, III and IV; and, l, m, n and o each are a repeating number not more than 0.5, satisfying the condition that l+m+n+o=1 and 0.4.ltoreq.o.ltoreq.0.5: ##STR2##

Resist polymer and chemical amplified resist composition containing the

This invention relates to a sulfonium salt, including its manufacturing method, which is effectively used as a photoacid initiator or radical photoinitiator during polymerization and a photoacid generator, leaving the protection groups of organic compounds, especially as an useful photoacid generator of the chemically amplified photoresist employed in semiconductor materials. Since the sulfonium salt of this invention, so prepared via one-step reaction between sulfoxide compound and aromatic compound in the presence of perfluoroalkanesulfonic anhydride, has the advantages in that by overcoming some shortcomings of the prior art to prepare the sulfonium salt via two steps using Grinard reagent, this invention may provide a novel sulfonium salt with higher yield which cannot be achieved in the prior art and also to prepare even any conventional sulfonium salt having better yield.

Sulfonium salt and its manufacturing method

A copolymer having a repeating unit represented by the following general formula I and a chemical amplification positive photoresist composition having the copolymer and a photoacid generator. The photoresist can allow for a good pattern shape even though a post-baking is taken in a somewhat delayed time and for a use of any radiation, such as uv light, deep uv light and charged particle beam. Also, it is superior in storage stability and resolution so that it is useful for the high integration of semiconductor devices. The polymer ranges, in polystyrene-reduced average molecular weight, from 1,000 to 1,000,000. The polymer is represented by the following repeating pattern: ##STR1## wherein, R.sub.1, R.sub.2 and R.sub.3 independently represent a hydrogen atom or a methyl; R.sub.4, R.sub.5 and R.sub.6 independently represent a hydrogen atom, an alkyl group, an alkoxy group or a halogen; 1, m, n each is a repeating number satisfying the condition that 0.3&lt;1/(m+n)&lt;0.9, 0.1&lt;m/(1+n)&lt;0.6 and 0.01&lt;n/(1+m)&lt;0.5; h and g, which may be different and the same, each are an integer of 0-8; and Am represents NR.sub.7 R.sub.8, a cyclic secondary amine, or a heterocyclic secondary amine containing an oxygen or sulfur atom, wherein R.sub.7 and R.sub.8 independently represent a hydrogen atom, an alkyl group, an aryl group or a phenyl group.

Copolymer useful for positive photoresist and chemical amplification

A positive chemical amplified photoresist composition having as a matrix resin a polymer having the repeating unit of Formula (I) and a photoacid generator. The polymer ranges, in polystyrene-reduced weight average molecular weight, from about 2,000 to 1,000,000. The photoresist composition is possible to develop in alkali and shows excellent sensitivity, resolution and transmissivity to deep uv light in addition to being superior in storage preservativity. The repeating unit of Formula (I) is: ##STR1## wherein, R.sub.2, R.sub.2 and R.sub.3 are independently represented by a hydrogen atom or a methyl group; R.sub.4 is a hydrogen atom, an alkyl group or an alkoxy group; R.sub.5 is functions as an acid-labile protective group and is selected from a t-butyl group, a tetrahydropyranyl group or an alkoxymethylene group; j is an integer of 1-8; k is an integer of 0-8; and 1, m and n each represent a mole ratio, satisfying the condition of l+m+n=1 where 0&lt;1&lt;0.4.

Polymer for positive photoresist and chemical amplified positive

There are disclosed an aromatic hydroxy compound or polymer substituted with acetal of Formula (I), (II) or (III), and a negative photoresist composition prepared therefrom. The pattern formed of the negative photoresist composition has good cross sections in addition to being superior in transmissivity to deep uv light and excimer laser and in thermal resistance and storage stability after exposure. ##STR1##

Acetal-substituted aromatic hydroxy compounds and negative photoresist

A chemical amplified positive photoresist composition including a resin having the repeating unit of Formula I and a photoacid generator. The resin ranges, in polystyrene-reduced molecular weight, from about 2,000 to 1,000,000. In Formula I, k and l each represent a mole ratio satisfying the condition of k+l=l. R.sub.1 is a hydrogen atom or a methyl group. R.sub.2 and R.sub.3 are independently either a hydrogen atom, a halogen atom, an alkyl group or an alkoxy group. R.sub.4 is an acetate group, a t-butoxycarbonyl group, a benzyl group, a trialkylsilyl group or an alkyl group. The photoacid generator which generates an acid by radiation. ##STR1##

Positive photoresist resin and chemical amplified positive photoresist

A three-component chemical amplified photoresist composition, comprising: an alkali soluble resin; a dissolution inhibitor of aromatic polyhydroxy compound substituted by at least two acid-decomposable radicals; and a photo acid generating agent of an onium salt, which is capable of forming good profiles when exposed to light with a short wavelength and is superior in heat resistance and storage stability.

Three-component chemical amplified photoresist composition

There are provided acetal group-containing alkoxy-styrene polymers represented by the following formula I: ##STR1## wherein R.sub.1 and R.sub.3 may be the same or different, and represent a hydrogen atom or a methylene group; R.sub.2 represents ##STR2## wherein R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8 may be the same or different, and independently represent a hydrogen atom, an alkyl group or an aryl group; m+n=1; k is an integer of 1-5; and l is an integer of 0-5; and an acid-generating agent, and chemical amplified negative photoresist composition comprising the same. It shows excellent transparency and sensitivity to deep UV in addition to being resistant to dry etching and alkali-developable.

Acetal group-containing alkoxy-styrene polymers, method of preparing the

A positive photoresist composition which is of high resolution, high sensitivity and wide focusing range and suitable for high integration of semiconductor devices and shows superior resist pattern profile, comprising quinonediazide sulfonic acid ester as a photoresist, an alkali soluble resin, a solvent, and additives, said quinonediazide sulfonic acid ester being prepared through the esterification of 1,2-naphthoquinonediazidesulfonyl halide or 1,2-benzoquinonediazidesulfonyl halide with an aromatic hydroxy compound represented by the following structural formula I: ##STR1## wherein R.sub.1 and R.sub.2 are independently hydrogen, halogen, an alkyl group or an alkoxy group; a is an integer of 1 to 3; b is an integer of 1 to 8; c is an integer of 1 to 12; and R.sub.3 is an alkyl group containing ether, mercapthane, sulfoxide, sulfone, aryl group or hydroxy group.

Positive photoresist composition

There are disclosed novel photoresist compositions employing phosphazene compounds as ballast, unabsorbent of light at a band of i-line and g-line and superior in thermal resistance and sensitivity as well as resolution, characterized by introducing photosensitive groups into phosphazene type ballast represented by the following formula I: ##STR1##

Positive photoresist composition containing naphthoquinone diazide

Copolymers comprising 1-50 mole % of sulfur dioxide and 50-99 mole % of trialkylgermylstyrene, having a weight average molecular weight of 500-10,000,000 and exhibiting a high sensitivity to light, electron beam, and X-ray, as well as having an excellent anti-dry etching resistance, and their application as a positive resisting material.

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Taejeon, South Korea

Seong-Ju Kim