A semiconductor photoresist composition includes an organotin compound represented by Chemical Formula 1 and a solvent. A method for forming patterns uses the semiconductor photoresist composition.

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Synthesis techniques are described for forming organotin trialkoxide compounds via direct alkylation of tin alkoxides. A first method involves reacting an alkali metal tin trialkoxide with an organohalide compound (RX.sub.n, where X is a halide atom and n?1) to form a monoorgano tin trialkoxide represented by the formula R[Sn(OR).sub.3].sub.n. The method can be used to form polytin trialkoxide compounds with a plurality of radiation sensitive CSn bonds. R and R include organo groups and can optionally comprise hetero-atoms and/or unsaturated bonds. A second method involves the ultraviolet light-driven reaction of a di-tin tetraalkoxide with an organohalide compound (RX) to form a monoorgano trialkoxide represented by the formula RSn(OR).sub.3. A third method involves the visible or ultraviolet light-driven reaction of a di-tin tetraalkoxide or an alkali metal tin trialkoxide with an fluorinated organohalide compound (R.sup.FX) to form a fluorinated monoorgano trialkoxide represented by the formula R.sup.FSn(OR).sub.3. The disclosed methods provide for high mono-organo specificity. Corresponding organotin trialkoxide compositions are also described. The compositions are useful for radiation patterning, especially with EUV radiation. The organotin trialkoxide compositions may be formed as radiation-patternable coatings on substrates.

A semiconductor photoresist composition and a method of forming patterns utilizing the same are provided. The semiconductor photoresist composition includes a condensed product produced by a condensation reaction between an organotin compound represented by Chemical Formula 1 and at least one organic acid compound selected from a substituted organic acid, an organic acid including at least two acid functional groups, and a substituted or unsubstituted sulfonic acid; and a solvent. ##STR00001##
Specific details of Chemical Formula 1 are as defined in the specification.

A pure composition comprises a monoalkyltin trialkoxide compound represented by the chemical formula RSn(OR).sub.3 or a monoalkyl tin triamide compound represented by the chemical formula RSn(NR.sub.2).sub.3 and no more than 4 mole % dialkyltin compounds relative to the total tin amount, where R is a hydrocarbyl group with 1-31 carbon atoms, and wherein R is a hydrocarbyl group with 1-10 carbon atoms. Methods are described for the formation of the pure compositions. A solid composition comprises a monoalkyl triamido tin compound represented by the chemical formula RSn-(NRCOR).sub.3, where R is a hydrocarbyl group with 1-31 carbon atoms, and where R and R are independently a hydrocarbyl group with 1-10 carbon atoms. The compositions are 10 suitable for the formation of resist compositions suitable for EUV patterning in which the compositions have a high EUV absorption.

Organotin clusters are described with the formula R.sub.3Sn.sub.3(O.sub.2CR).sub.5-x(OH).sub.2+x(?.sub.3-O) with 0?x<2; R=branched or cycloalkyl with 1 to 31 carbon atoms; R?H or alkyl with 1 to 20 carbon atoms. Three carboxylato ligands are bridging, and two OH ligands are bridging. The remaining two carboxylato ligands are in non-bridging configurations, and the non-bridging carboxylato ligands are exchangeable in solution. Solutions of these clusters are suitable for forming radiation sensitive coatings that can be used to pattern nanometer scale structures. The radiation sensitive coatings are particularly suitable for EUV patterning.

A composition contains a compound represented by the following formula: ##STR00001##
where M represents either of Si and Sn, R.sub.1 to R.sub.8 each independently represent an alkyl group containing three or less carbon atoms, and R.sub.9 to R.sub.14 each independently represent an alkyl group.

Provided are an organometallic compound represented by one of Formulas 1-1 to 1-4 below.

##STR00001## a resist composition including the same, and a pattern forming method using the same. For descriptions of M.sub.11, L.sub.11 to L.sub.14, a11 to a14, R.sub.11 to R.sub.14, X.sub.11 to X.sub.14, n11 to n15, Y.sub.11 to Y.sub.13, and R.sub.15 to R.sub.17 in Formulas 1-1 to 1-4, refer to the specification.

Provided are a resist composition and a method of forming a pattern by using the same, the resist composition including: an organometallic compound represented by Formula 1; and a polymer including a repeating unit containing a radical generating group, a repeating unit containing a radical accepting group, or any combination thereof.

Sn(R.sub.11).sub.n(OR.sub.12).sub.(4-n) Formula 1

Descriptions of R.sub.11, R.sub.12 and n in Formula 1 are provided in the specification.

Provided are a resist composition and a method of forming a pattern using the same, the resist composition including an organometallic compound represented by Formula 1 below, and a polymer including a repeating unit represented by Formula 2 below:

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wherein, in Formulas 1 and 2, M.sub.11, R.sup.11, R.sub.12, n, A.sub.21, L.sub.21 to L.sub.23, a21 to a23, R.sub.21 to R.sub.24, b22, p, and X.sub.21 are as described in the specification.

Provided are a resist composition and a pattern forming method using the same. The resist composition may include an organometallic compound represented by Formula 1 below and a polymer repeating unit represented by Formula 2 below.

##STR00001##

In Formulas 1 and 2, descriptions of M.sub.11, R.sub.11, R.sub.12, n, A.sub.21, L.sub.21 to L.sub.24, a21 to a24, R.sub.21, R.sub.22, b22, p, and X.sub.21 refer to the specification.