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US 12,535,735 B2Granted
Modified thioxanthone photoinitiators
AssigneesLintfield Limited, Tokyo Electron Limited
InventorsChristopher Wall, Cong-Que Dinh, Seiji Nagahara
Life of this patent
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Abstract
Latent photoinitiator compounds are described, as well as compositions containing such compounds and their uses in photoinitiated methods for producing photoresist structured.
Claims32
A compound of the Formula I:
- wherein:
- n=0 or 1;
- m=0, 1, 2 or 3;
- R1 and R2 are independently selected from a C1-6 alkylhydroxy group or a carboxylate ester thereof, a C1-6 alkylthio group, a C1-6 alkylamino group, and a C1-6 carboxylate ester group wherein the ester portion comprises a C1-6 alkyl group and/or a 4- to 10-membered carbocyclic group;
- and
- R3, R4, R5, R6, R7 and R8 are independently selected from H, a hydroxy group, a C1-6 alkyl group, a C2-6 alkenyl group, a C1-6 alkoxy group, a C1-6 alkylthio group, a 4- to 8-membered carbocyclic group, a 4- to 8-membered heterocyclic group, and a C1-6 carboxylate ester group wherein the ester portion comprises a C1-6 alkyl group and/or a 4- to 10-membered carbocyclic group;
- or wherein R5 forms with R3 or an R7 and the carbon atoms to which they are attached a 4- to 8-membered carbocyclic group or a 4- to 8-membered heterocyclic group.
4 more elements
A compound of Formula II:
- wherein:
- m=0, 1, 2, 3 or 4;
- and
- one of the aromatic rings is di-substituted, at the 3 and 4 positions of the thioxanthone ring, with substituents independently selected from —O—C(1-6)alkylhydroxy group or a carboxylate ester thereof, a —O—C(1-6)alkylthio group, a —O—C(1-6)alkylamino group, and a —O—C(1-6)carboxylate ester group wherein the ester portion comprises a C1-6 alkyl group and/or a 4- to 10-membered carbocyclic group, wherein the 3 and 4 position substitution optionally produces a 5-membered benzodioxole ring;
- or
- one or both of the aromatic rings is substituted with at least one substituent independently selected from hydroxy, alkoxy, benzyloxy, alkylcarbonate, hydroxyalkyl, acetal, ester, oxyacetic acid and esters thereof, aryloxy and arylthio;
- and
- L=a linker group.
5 more elements
A compound selected from:
- 2-[4′-(2-acetoxyethoxy)spiro[1,5-dihydro-2,4-benzodioxepine-3,9′-thioxanthene]-3′-yl]oxyethyl acetate;
- 2-[4′-(2-hydroxyethoxy)spiro[1,5-dihydro-2,4-benzodioxepine-3,9′-thioxanthene]-3′-yl]oxyethanol;
- 2-[4′-(2-acetoxyethoxy)-5-phenyl-spiro[1,3-dioxane-2,9′-thioxanthene]-3′-yl]oxyethyl acetate;
- 2-[4′-(2-hydroxyethoxy)-5-phenyl-spiro[1,3-dioxane-2,9′-thioxanthene]-3′-yl]oxyethanol;
- 2-[4′-(2-acetoxyethoxy)-5,5-dimethyl-spiro[1,3-dioxane-2,9′-thioxanthene]-3′-yl]oxyethyl acetate;
- 2-[4′-(2-hydroxyethoxy)-5,5-dimethyl-spiro[1,3-dioxane-2,9′-thioxanthene]-3′-yl]oxyethanol;
- 2-[4′-(2-acetoxyethoxy)spiro[1,3-dioxepane-2,9′-thioxanthene]-3′-yl]oxyethyl acetate;
- 2-[4′-(2-hydroxyethoxy)spiro[1,3-dioxepane-2,9′-thioxanthene]-3′-yl]oxyethanol;
- 2-[4′-(2-acetoxyethoxy)spiro[1,3-dioxane-2,9′-thioxanthene]-3′-yl]oxyethyl acetate;
- 2-[4′-(2-hydroxyethoxy)spiro[1,3-dioxane-2,9′-thioxanthene]-3′-yl]oxyethanol;
- 2-[4′-(2-acetoxyethoxy)-5-[4-[3′,4′-bis(2-acetoxyethoxy)spiro[1,3-dioxane-2,9′-thioxanthene]-5-yl]phenyl]spiro[1,3-dioxane-2,9′-thioxanthene]-3′-yl]oxyethyl acetate;
- 2-[5-[4-[3′,4′-bis(2-hydroxyethoxy)spiro[1,3-dioxane-2,9′-thioxanthene]-5-yl]phenyl]-4′-(2-hydroxyethoxy)spiro[1,3-dioxane-2,9′-thioxanthene]-3′-yl]oxyethanol;
- 2-{3′-[2-(acetyloxy) ethoxy]-5-{4′-[2-(acetyloxy) ethoxy]-3′-{2-[(1-hydroxyethenyl)oxy]ethoxy}spiro[1,3-dioxane-2,9′-thioxanthen]5-yl}spiro[1,3-dioxane-2,9′-thioxanthen]-4′yloxy}ethyl acetate;
- 2-{5′-[3′,4′-bis(2-hydroxyethoxy)spiro[1,3-dioxane-2,9′thioxanthen]-5-yl]-3′-(2-hydroxyethoxy)spiro[1,3-dioxane-2,9′thioxanthen]-4′-yloxy}ethan-1-ol;
- 2-{3,4′″-bis[2-(acetyloxy) ethoxy]-3″′-{2-[(1-hydroxyethenyl)oxy]ethoxy}trispiro[thioxanthene-9,2′:
- 5′m5″-bis([1,3]dioxane)-2″,9′″-thioxanthen]4-yloxy}ethyl acetate;
- 2-[3,3′″,4′″-tris(2-hydroxyethoxy) trispiro[thioxanthene-9,2′:
- 5′,5″-bis([1,3]dioxane)-2″,9′″-thioxanthen]-4-yloxy]ethan-1-ol;
- 2-{3′-[2-acetyloxy) ethoxy]-5-{4′-[2-(acetyloxy) ethoxy]-3′-{2-[(1-hydroxyethenyl)oxy]ethoxy}spiro[1,3-dioxane-2,9′thioxanthen]-5-yl}spiro[1,3-dioxane-2,9′-thioxanthen]-4′yloxy}ethyl acetate;
- 2-{5-[3′,4′-bis(2-hydroxyethoxy)spiro[1,3-dioxane-2,9′-thioxanthen]-5-yl]-3′-(2-hydroxyethoxy)spiro[1,3-dioxane-2,9′-thioxanthen]4′-yloxy}ethan-1-ol;
- 2-{3″,4″,6-tris[2-acetyloxy) ethoxy]-1′,5′,5′a,6′,10′,10′a-hexahydrospiro[thioxanthene-9,8′-[2,4,7,9]tetraoxaheptalene-3′,9″thioxanthen]-5-yloxy}ethyl acetate;
- 2-[3″,4″,6-tris(2-hydroxyethoxy)-1′,5′,5′a,6′,10′,10′a-hexahydrodispiro[thioxanthene-9,8′-[2,4,7,9]tetraoxaheptalene-3′,9″-thioxanthen]5-yloxy]ethan-1-ol;
- 2-[4′-(2-acetoxyethoxy)-5-[2-[3′,4′-bis(2-acetoxyethoxy)spiro[1,3-dioxane-2,9′-thioxanthene]-5-yl]ethyl]spiro[1,3-dioxane-2,9′-thioxanthene]-3′-yl]oxyethyl acetate;
- 2-[5-[2-[3′,4′-bis(2-hydroxyethoxy)spiro[1,3-dioxane-2,9′-thioxanthene]-5-yl]ethyl]-4′-(2-hydroxyethoxy)spiro[1,3-dioxane-2,9′-thioxanthene]-3′-yl]oxyethanol;
- or 5-[2-(3′,4′-dimethoxyspiro[1,3-dioxane-2,9′-thioxanthene]-5-yl) ethyl]-3′,4′-dimethoxy-spiro[1,3-dioxane-2,9′-thioxanthene].
22 more elements
Dependencies are inferred from the claim text.