A hydroximic acid-metal hydroxide coordination complex and preparation and application thereof are disclosed. The hydroximic acid-metal hydroxide coordination complex is formed by a coordination of hydroximic acid with divalent or higher valent metal ions under an alkaline condition. The hydroximic acid-metal hydroxide coordination complex has a strong selectivity and a strong collection ability for metal oxide minerals such as tungsten-containing minerals, ilmenite, rutile, cassiterite, and rare earth. The preparation method is simple and low in costs, and is beneficial to industrialized production.

Organotin clusters are described with the formula R.sub.3Sn.sub.3(O.sub.2CR′).sub.5-x(OH).sub.2+x(μ.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 semiconductor resist composition includes an organometallic compound represented by Chemical Formula 1 and a solvent: ##STR00001## wherein, in Chemical Formula I, R.sup.1 is an aliphatic hydrocarbon group, an aromatic hydrocarbon group, or an —alkylene-O-alkyl group, and R.sup.2 to R.sup.4 are each independently selected from —OR.sup.a and —OC(═O)R.sup.b, where R.sup.a is not hydrogen.

A resist material is combined with a ligand containing four or more fluorine atoms and is represented by the following formula: [(R.sup.1M).sub.iO.sub.jX.sub.k(OH).sub.m] (OH).sub.nR.sup.2.sub.p, wherein one of “R.sup.1” and “R.sup.2” is C.sub.aF.sub.bH.sub.c, C.sub.aF.sub.bH.sub.cN.sub.d, C.sub.aF.sub.bH.sub.cP.sub.d, C.sub.aF.sub.bH.sub.cS.sub.d, C.sub.aF.sub.bH.sub.cO.sub.d, C.sub.aF.sub.bH.sub.cN.sub.dS.sub.e, C.sub.aF.sub.bH.sub.cP.sub.dS.sub.e, C.sub.aF.sub.bH.sub.cN.sub.dO.sub.e, or C.sub.aF.sub.bH.sub.cP.sub.dO.sub.e, the other of “R.sup.1” and “R.sup.2” is C.sub.aH.sub.c, C.sub.aF.sub.bH.sub.c, C.sub.aF.sub.bH.sub.cN.sub.d, C.sub.aF.sub.bH.sub.cP.sub.d, C.sub.aF.sub.bH.sub.cS.sub.d, C.sub.aF.sub.bH.sub.cO.sub.d, C.sub.aF.sub.bH.sub.cN.sub.dS.sub.e, C.sub.aF.sub.bH.sub.cP.sub.dS.sub.e, C.sub.aF.sub.bH.sub.cN.sub.dO.sub.e, or C.sub.aF.sub.bH.sub.cP.sub.dO.sub.e, “a” and “c” are each independently an integer of 0 to 20, “b” is an integer of 4 to 30, “d” and “e” are each independently an integer of 0 to 5, “M” is one metal selected from a specified list, “i” is an integer from 1 to 12, “j” is an integer of 1 to 14, “X” is a halogen selected from a specified list, “k” and “m” are each independently an integer of 0 to 6, and “n” and “p” are each independently an integer of 0 to 2.

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—(NR′COR″).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 suitable for the formation of resist compositions suitable for EUV patterning in which the compositions have a high EUV absorption.

Disclosed are a semiconductor photoresist composition including an organometallic compound including at least one selected from compounds represented by Chemical Formulae 1 to 3 and a solvent, and a method of forming patterns using the semiconductor photoresist composition on an etching-objective layer to form a photoresist layer, patterning the photoresist layer to form a photoresist pattern, and etching the etching-objective layer using the photoresist pattern as an etching mask.

##STR00001##

The present disclosure is directed to organotin cluster compounds having formula (I) and their use as photoresists in extreme ultraviolet lithography processes.

##STR00001##

Provided is a mono-tin organic compound for the synthesis of sucrose-6-carboxylate. The compound has a structure shown in formula (1), wherein R.sub.1, R.sub.2, and R.sub.3 each are independently selected from the group consisting of C.sub.1 to C.sub.8 linear or branched saturated alkyl, C.sub.2 to C.sub.8 linear or branched unsaturated alkyl, C.sub.3 to C.sub.8 substituted or unsubstituted saturated cycloalkyl, C.sub.3 to C.sub.8 substituted or unsubstituted unsaturated cycloalkyl, and C.sub.6 to C.sub.12 aryl or substituted aryl; and R.sub.4 is selected from the group consisting of C.sub.1 to C.sub.6 linear or branched saturated alkyl and C.sub.6 to C.sub.12 aryl or substituted aryl.

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 suitable for the formation of resist compositions suitable for EUV patterning in which the compositions have a high EUV absorption.

The present disclosure includes the preparation of mixed-ligand compounds, such as tin(II) cyclopentadienylide complexes. The compounds of the present disclosure can be used as atomic layer deposition (ALD) precursors for extreme ultraviolet (EUV) lithography. The compounds of the present disclosure can also be used as plasma chemical vapor deposition (CVD) precursors for EUV lithography.