Stability-enhanced organotin photoresist compositions

Patent metadata

Field	Value
Publication number	US-2023143592-A1
Application number	US-202217982013-A
Country	US
Kind code	A1
Filing date	Nov 7, 2022
Priority date	Nov 8, 2021
Publication date	May 11, 2023
Grant date	—

Abstract

An organotin precursor solution is described comprising an organic solvent, an optional additive, and an organotin composition represented by one or more organotin compounds represented by the formula RSnL3, wherein each R is independently a hydrocarbyl ligand having from 1 to 31 carbon atoms and each L is independently a hydrolysable ligand, wherein the total concentration of Sn is from about 0.001 M to about 0.5 M. The solvent can comprises a linear alcohol with from 1 to 6 carbon atoms, and the organotin precursor solution can have an initial water content from about 100 ppm to about 10,000 ppm, in which the organotin precursor solution has a reduced rate of water dissipation relative to an equivalent organotin precursor solution formed with 4-methyl-2-pentanol. The organotin precursor solutions can be prepared through the selection of an appropriate stabilizing compound, which can be a linear, short chain alcohol and an appropriate additive.

First claim

What is claimed is:

1 . An organotin precursor solution comprising an organic solvent and an organotin composition represented by one or more organotin compounds represented by the formula RSnL 3 , wherein each R is independently a hydrocarbyl ligand having from 1 to 31 carbon atoms and each L is independently a hydrolysable ligand, wherein the total concentration of Sn is from about 0.001M to about 0.5 M, wherein the solvent comprises a linear alcohol with from 1 to 6 carbon atoms, wherein the organotin precursor solution has an initial water content from about 100 ppm to about 10,000 ppm and wherein the organotin precursor solution has a reduced rate of water dissipation relative to an equivalent organotin precursor solution formed with 4-methyl-2-pentanol.

2 . The organotin precursor solution of claim 1 wherein the organic solvent comprises a solvent blend and wherein the linear alcohol is a cosolvent present at a concentration from about 5 vol % to about 75 vol % relative to the total solvent, and wherein the solution has a room temperature viscosity from about 0.5 cP to about 20 cP.

3 . The organotin precursor solution of claim 1 wherein the initial water content is normalized from about 100 ppm to about 5,000 ppm.

4 . The organotin precursor solution of claim 1 wherein the measurable water content is at least about 100 ppm a week after preparation.

5 . The organotin precursor solution of claim 1 wherein the organic solvent comprises a secondary or a tertiary alcohol or a combination thereof.

6 . The organotin precursor solution of claim 1 wherein the organic solvent comprises 4-methyl-2-pentanol.

7 . The organotin precursor solution of claim 2 wherein the cosolvent comprises methanol, ethanol, n-propanol, n-butanol, 1-pentanol, or mixtures thereof.

8 . The organotin precursor solution of claim 1 wherein the organic solvent comprises a blend of two primary alcohols.

9 . The organotin precursor solution of claim 2 wherein the cosolvent is present at a concentration from about 25 vol % to 55 vol % relative to the total solvent.

10 . The organotin precursor solution of claim 2 wherein at least a portion of the cosolvent is coordinated with the RSnL 3 as a ligand.

11 . The organotin precursor solution of claim 10 wherein the solvent comprises a primary alcohol represented by the formula R′ OH, wherein R′ comprises a hydrocarbyl ligand having from 1 to 10 carbon atoms, and wherein the solution comprises a composition represented by the formula RSnL y ([H]OR′) x , wherein x is 1 or 2 or a combination thereof, where OR′ may or may not be deprotonated and y is determined accordingly for charge balance.

12 . The organotin precursor solution of claim 1 wherein the organotin precursor solution has no observable precipitation for at least a week when stored in a sealed container.

13 . The organotin precursor solution of claim 1 wherein the hydrocarbyl ligand comprises a linear alkyl group, a branched alkyl group, a cycloalkyl group, an aryl group, an alkenyl group, an alkynyl group, heteroatom derivatives thereof, or a combination thereof.

14 . The organotin precursor solution of claim 1 wherein the organotin composition comprises one or more R ligands chosen from t-amyl, t-butyl, iso-propyl, n-butyl, methyl, or a combination thereof.

15 . The organotin precursor solution of claim 1 wherein the organotin composition has R ligands comprising a blend of a linear alkyl ligand and a non-linear alkyl ligand.

16 . The organotin precursor solution of claim 15 wherein the non-linear alkyl ligand comprises a branched alkyl group, a cyclo-alkyl group, or an aryl group.

17 . The organotin precursor solution of claim 1 wherein the organotin composition has R ligands comprising methyl ligands and t-butyl ligands.

18 . The organotin precursor solution of claim 1 wherein the organotin composition has L ligands comprising a dialkylamide, an alkylsilylamide, an alkoxide, an alkylacetylide, or a combination thereof.

19 . The organotin precursor solution of claim 1 wherein the organotin composition has L ligands comprising methoxide, ethoxide, propoxide, iso-propoxide, butoxide, iso-butoxide, tert-butoxide, tert-amyloxide, or combinations thereof.

20 . The organotin precursor solution of claim 1 further comprising SnL′ 4 , wherein L′ is a hydrolysable ligand that is the same or different than L, and wherein the concentration of the SnL′ 4 is up to 20 mol. % of the total Sn.

21 . The organotin precursor solution of claim 1 further comprising an additive, wherein the additive is present at a concentration from about 0.01 moles to about 3 moles per mole of Sn.

22 . The organotin precursor solution of claim 21 wherein the additive comprises a diol, a triol, an amino alcohol, an amide, or a 1,3-diketone.

23 . The organotin precursor solution of claim 21 wherein the additive comprises ethylene glycol, propylene glycol, 1,2-butanediol, glycerol, ethanolamine, diethanolamine, triethanolamine, dimethylformamide, dimethylurea, or acetylacetone.

24 . The organotin precursor solution of claim 21 wherein the additive comprises a carboxylic acid represented by the formula R″COOH.

25 . The organotin precursor solution of claim 24 wherein the precursor solution comprises a soluble composition represented by the formula (RSn) 12 O 14 (OH) 8−n (O 2 CR″) n .

26 . A radiation patternable film comprising an organotin composition having an oxo-hydroxo network that is formed from the organotin precursor solution of claim 1 under conditions allowing hydrolysis of hydrolysable ligands.

27 . The film of claim 26 wherein the film, when fully hydrolyzed, can be represented by the formula RSnO (1.5−(x/2)) (OH) x where 0<x≤3.

28 . A radiation patternable film formed from the organotin precursor solution of claim 21 , wherein the radiation patternable film comprises additive ligands.

Assignees

• Inpria Corp

Inventors

• Jiang Kai
• Telecky Alan J
• Meyers Stephen T

Classifications

• G03F7/0048

  characterised by the solvents or agents facilitating spreading, e.g. tensio-active agents · CPC title

• G03F7/0043 Primary

  Chalcogenides; Silicon, germanium, arsenic or derivatives thereof; Metals, oxides or alloys thereof (G03F7/0044 takes precedence) · CPC title

• C07F7/2224

  Compounds having one or more tin-oxygen linkages · CPC title

• G03F7/0042 Primary

  with inorganic or organometallic light-sensitive compounds not otherwise provided for, e.g. inorganic resists (G03F7/075 takes precedence) · CPC title