TWI455915B - 光酸產生劑、其製造方法以及含有其的抗蝕劑組成物 - Google Patents

光酸產生劑、其製造方法以及含有其的抗蝕劑組成物 Download PDF

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TWI455915B
TWI455915B TW101103769A TW101103769A TWI455915B TW I455915 B TWI455915 B TW I455915B TW 101103769 A TW101103769 A TW 101103769A TW 101103769 A TW101103769 A TW 101103769A TW I455915 B TWI455915 B TW I455915B
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independently represent
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photoacid generator
alkyl
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Jung-Hoon Oh
Jin Bong Shin
Tae Gon Kim
Dong Chul Seo
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Korea Kumho Petrochem Co Ltd
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    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/07—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
    • C07C309/09—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton
    • C07C309/10—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton with the oxygen atom of at least one of the etherified hydroxy groups further bound to an acyclic carbon atom
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    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/32—Oxygen atoms
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    • G03F7/004—Photosensitive materials
    • G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
    • G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
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    • G03F7/0397—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition the macromolecular compound having an alicyclic moiety in a side chain
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    • G03F7/20—Exposure; Apparatus therefor
    • G03F7/2041—Exposure; Apparatus therefor in the presence of a fluid, e.g. immersion; using fluid cooling means
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    • C07C2601/14—The ring being saturated
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    • C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms
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  • Plural Heterocyclic Compounds (AREA)

Claims (9)

  1. 一種光酸產生劑，如下列式(1)表示， 其中，在式(1)中，Y1與Y2各自獨立表示由烷基、烯基、烷氧基、環烷基、雜環烷基、芳基以及雜芳基所組成的族群中選出之任一者；X表示由烷二基、烯二基、NR’、S、O、CO以及其組合所組成的族群中選出之任一者，而R’表示由氫原子以及烷基所組成的族群中選出之任一者；R1及R2各自獨立表示由氫原子、烷基、烷氧基、全氟烷基、全氟烷氧基、鹵素原子、羥基、羧基、氰基、硝基、胺基以及硫基所組成的族群中選出之任一者；n1表示1或2的整數；n2表示0至5的整數；以及A+表示有機反離子。
  2. 如申請專利範圍第1項所述的光酸產生劑，其中Y1與Y2各自獨立表示由烷基、烯基、烷氧基、環戊 基、環己基、十氫化萘基、8氫-1H-茚基、金剛烷基、降莰基、四氫氟喃基、具有含10至30個碳原子的降莰基的多環環烷基、苯基、萘基、聯苯基、蔥基、菲基、茀基、芘基、萉基、茚基、伸聯苯基、二苯甲基、四氫化萘基、二氫化蔥基、四苯甲基以及三苯甲基所組成的族群中選出之任一者。
  3. 如申請專利範圍第1項所述的光酸產生劑，其中Y1與Y2各自獨立表示由烷基、烯基、烷氧基、下列式(1-a)至式(1-i)以及式(2-a)至式(2-l)所組成的族群中選出之任一者： 其中，在式(1-a)至(1-i)中，R11及R12各自獨立表示由氫原子、烷基、烷氧基、全氟烷基、全氟烷氧基、鹵素原子、羥基、羧基、氰基、硝基、胺基、硫基、甲硫基、甲氧基、OR’、COR’、COOR’、O以及S所組成的族群中選出之任一者，而R’表示由烷基以及芳基所組成的族群中選出之任一者；R21表示由CR24R25、O、CO、S以及NR23所組成的族群中選出之任一者；R23至R25各自獨立表示由氫原子、烷基以及芳基所組成的族群中選出之任一者；a、c以及d各自獨立表示0至9的整數；b表示0至11的整數；e表示0至15的整數；f表示0至7的整數；0c+d17，而0c+f15； 其中，在式(2-a)至式(2-l)中，R11、R12、R13以及R14各自獨立表示由烷基、烷氧基、全氟烷基、全氟烷氧基、鹵素原子、羥基、氰基、硝基、胺基以及硫基所組成的族群中選出之任一者；R21及R22各自獨立表示由CR24R25、O、CO、S以及NR23所組成的族群中選出之任一者；R23至R25各自獨立表示由氫原子、烷基以及芳基所組成的族群中選出之任一者；a、h以及i各自獨立表示0至5的整數；b表示0至3的整數；c以及d各自獨立表示0至4的整數；e、f以及g各自獨立表示0至2的整數；且0c+d+e9。
  4. 如申請專利範圍第1項所述的光酸產生劑，其中所述光酸產生劑為由下列式(3-1)至式(3-14)代表 之化合物所組成的族群中選出之任一者：
  5. 一種光酸產生劑的製造方法，所述製造方法包括：第一步驟，使羥基磺酸鹽與環氧乙烷反應，從而製造羥基乙氧磺酸鹽；以及第二步驟，使前述製得的羥基乙氧磺酸鹽與羰基鹵化物反應，從而製得中間產物；以及第三步驟，使從而製得的所述中間產物發生陽離子的 取代反應，藉此製造式(1)表示的化合物： 其中，在式(1)中，Y1與Y2各自獨立表示由烷基、烯基、烷氧基、環烷基、雜環烷基、芳基以及雜芳基所組成的族群中選出之任一者；X表示由烷二基、烯二基、NR’、S、O、CO以及其組合所組成的族群中選出之任一者；R’表示由氫原子以及烷基所組成的族群中選出之任一者；R1及R2各自獨立表示由氫原子、烷基、烷氧基、全氟烷基、全氟烷氧基、鹵素原子、羥基、羧基、氰基、硝基、胺基以及硫基所組成的族群中選出之任一者；n1表示1或2的整數；n2表示0至5的整數；以及A+表示有機反離子。
  6. 如申請專利範圍第5項所述的光酸產生劑的製造方法，其中所述羥基磺酸鹽由下列式(6)表示， 所述環氧乙烷由下列式(7)表示所述羥基乙氧磺酸鹽由下列式(8)表示所述羰基鹵化物由下列式(9)表示，以及所述中間產物由下列式(10)表示： 其中，在式(6)至式(10)中，Y1與Y2各自獨立表示由烷基、烯基、烷氧基、環烷基、雜環烷基、芳基以及雜芳基所組成的族群中選出之任一者；X表示由烷二基、烯二基、NR’、S、O、CO以及其組合所組成的族群中選出之任一者；R’表示由氫原子以及烷基所組成的族群中選出之任一者；R1及R2各自獨立表示由氫原子、烷基、烷氧基、全氟烷基、全氟烷氧基、鹵素原子、羥基、羧基、氰基、硝基、胺基以及硫基所組成的族群中選出之任一者；Rx表示鹵素原子；n1表示1或2的整數； n2表示0至5的整數；以及M+表示鹼金屬離子。
  7. 如申請專利範圍第5項所述的光酸產生劑的製造方法，其中由所述第一步驟與所述第二步驟以及其組合所組成的族群中所選出的任一步驟是藉由在酸性催化劑和鹼性催化劑組成的族群中選出的任一催化劑的存在下使反應進行來完成。
  8. 如申請專利範圍第5項所述的光酸產生劑的製造方法，其中所述第二步驟可藉由使所述羥基乙氧磺酸鹽和所述羰基鹵化物在20℃至100℃下反應1小時到12小時來完成。
  9. 一種抗蝕劑組成物，包括如申請專利範圍第1項至第4項中任一項所述的光酸產生劑。
TW101103769A 2011-02-07 2012-02-06 光酸產生劑、其製造方法以及含有其的抗蝕劑組成物 TWI455915B (zh)

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