US 9,063,416 B2  197  198  TABLE 20-continued  TABLE21  Examples 1 to 25, Comparative Examples 1 to 12  The components shown in Tables 22 to 24 were mixed  together and dissolved to obtain resist compositions.  TABLE22  Compound  5-42  5-43  5-44  5-45  5-47  5-48  5-49  5-50  5-51  5-52  5-53  Anion  Cation  NMR  analysis  an-5  ca-42  $^{1}$H-NMR:  I,  (ppm)- 7.80-7.92 (m, l0H,ArH), 7.67 (s, 2H,ArH), 4.66 (s, 2H, CH2), 4.12(s, 2H, CH2),  an-5  ca-43  an-5  ca-44  an-5  ca-45  an-5  ca-47  an-5  ca-48  an-5  ca-49  an-5  ca-50  an-5  ca-51  an-5  ca-52  an-5  ca-53  2.31-2.43 (m, 7H, ArCH3 + CH), 2.13-2.16 (m, 2H, cyclohexyl), 1.97-2.02 (m, 4H, CH2 + CH2), 1.14-1.68 (m,  9H, cyclohexyl + CH), 0.84-1.15 (t, 12H, CH3)  $^{1}$H-NMR:  I,  (ppm)- 8.44 (d, lH,ArH), 8.22 (m, 2H,ArH), 7.73-7.89 (m, 13H,ArH), 7.50 (d, lH,ArH),  4.12(s, 2H, CH2), 2.31-2.43(m, lH, CH), 1.87-2.02(m, 2H, CH2), 1.49-1.68(m, lH, CH), 0.85-1.15(m, 9H, CH3 +  CH3 +CH3)  $^{1}$H-NMR:  I,  (ppm) - 8.24 (d, 4H, ArH), 7.59 (t, 2H, ArH), 7.47 (t, 4H, ArH), 4.12(s, 2H, CH2), 2.31-2.43(m,  lH, CH), 1.87-2.02(m, 2H, CH2), 1.49-1.68(m, lH, CH), 0.85-1.15(m, 9H, CH3 + CH3 + CH3)  $^{1}$H-NMR:  I,  (ppm)- 8.55 (d, 2H,ArH), 8.38 (d, 2H,ArH), 8.32 (d, 2H,ArH), 8.03 (d, 2H,ArH), 7.93-7.97  (m, lH, ArH), 7.82-7.88 (m, SH, ArH), 7.55 (d, 2H, ArH), 4.12(s, 2H, CH2), 2.31-2.43(m, lH, CH), 1.87-2.02(m,  2H, CH2), 1.49-1.68(m, lH, CH), 0.85-1.15(m, 9H, CH3 + CH3 + CH3)  $^{1}$H-NMR:  I,  (ppm)- 4.46 (s, 2H, CH2(C=O)), 4.12(s, 2H, CH2), 3.38-3.58 (m, 4H, CH2SCH2), 1.49-2.43 (m,  25H,Adamantyl + CH2CH2 +CH+ CH2), 0.85-1.15(m, 9H, CH3 + CH3 + CH3)  $^{1}$H-NMR:  I,  (ppm)- 7.75 (s, 2H,Ar), 4.12(s, 2H, CH2), 3.91-3.96 (m, 2H, CH2), 3.72-3.79 (m, 2H,  CH2), 2.29-2.43(m,  SH,  CH2 + CH), 1.49-2.19(m, 24H,Ar---CH3 +Adamantane + CH2 + CH), 0.85-1.15(m, 9H,  CH3+CH3+CH3)  $^{1}$H-NMR:  I,  (ppm)- 7.82 (m, 2H,Ar), 4.12(s, 2H, CH2), 3.73-3.91(m, 4H CH2), 1.49-2.43(m, 31H,  Ar---CH3 + CH2 +CH+ adamantane), 0.85-1.15(m, 9H, CH3 + CH3 + CH3)  $^{1}$H-NMR:  I,  (ppm)- 8.23 (d, 4H,ArH), 7.98 (d, 4H,ArH), 4.12(s, 2H, CH2), 2.31-2.43(m, lH, CH), 1.87- 2.02(m, 2H, CH2), 1.49-1.68(m, lH, CH), 1.37 (s, 18H, CH3 oftert-butyl), 0.85-1.15(m, 9H, CH3 + CH3 + CH3)  $^{19}$F-NMR:  I,  (ppm) - -48.5  $^{1}$H-NMR:  I,  (ppm) - 7.77-7.98 (m, !OH, ArH), 7.64 (s, 2H, ArH), 4.57(s, 2H, CH2O), 4.12(s, 2H, CH2),  2.40 (s, 6H, CH3), 2.02-2.26 (m, 9H, Adamantane), 1.76 (br s, 6H, Adamantane)  $^{1}$H-NMR:  I,  (ppm)- 7.77-7.89 (m, l0H,ArH), 7.64 (s, 2H,ArH), 5.70(t, lH, OCHC=O), 4.82 (s, 2H,  ArOCH2), 4.12(s, 2H, CH2), 4.46-4.30 (m, 2H, OCOCH2), 2.71-2.64 (m, lH, OCH2CH2), 2.24-2.43 (m, SH,  CH3 + OCH2CH2 + CH), 1.87-2.02(m, 2H, CH2), 1.49-1.68(m, lH, CH), 0.85-1.15(m, 9H, CH3 + CH3 + CH3)  $^{1}$H-NMR:  I,  (ppm)- 8.28 (d, 2H,ArH), 8.11 (d, lH,ArH), 7.86(t, lH,ArH), 7.63-7.Sl(m, 7H,ArH),  4.12(s, 2H, CH2), 2.31-2.43(m, lH, CH), 1.87-2.02(m, 2H, CH2), 1.49-1.68(m, lH, CH), 0.85-1.15(m, 9H,  CH3+CH3+CH3)  Compound  5-54  5-55  5-56  5-57  5-58  5-59  5-60  Anion  Cation  NMR analysis  an-5  ca-54  $^{1}$H-NMR:  I,  (ppm)- 8.05 (d, 2H,ArH), 7.74 (d, 2H,ArH), 4.12(s, 2H, CH2), 3.85(s, 3H, S---CH3), 1.87- 2.02(m, 2H, CH2), 1.49-1.68(m, lH, CH), 1.30(s, 18H, t-Bu), 0.85-1.15(m, 9H, CH3 + CH3 + CH3)  an-5  ca-55  $^{1}$H-NMR:  I,  (ppm) - 8.41 (m, 2H ArH), 8.12(d, lH, ArH), 7.73-7.93(m, 2H, ArH), 7.19(d, lH, ArH),  5.23(s, 2H, CH2), 4.95(m, lH, Adamantane), 4.03(m, 2H, CH2S), 4.12(s, 2H, CH2), 3.75(m, 2H, CH2S),  2.27-2.43(m,  SH,  SCH2CH2 + CH), 1.42-2.02(m, 17H,Adamantyl +CH+ CH2), 0.85-1.15(m, 9H, CH3 +  CH3 +CH3)  an-5  ca-56  $^{1}$H-NMR:  I,  (ppm) - 8.42(m, 2H ArH), 8.17(d, lH, ArH), 7.78-7.91(m, 2H, ArH), 7.23(d, lH, ArH), 5.26(s, 2H,  CH2), 3.75-4.19(m, 9H, SCH2 + CH3 + CH2), 2.29-2.60(m, 5H, SCH2CH2 + CH), 1.87-2.02(m, 2H, CH2), 1.49- 1.68(m, lH, CH), 0.85-1.15(m, 9H, CH3 + CH3 + CH3)  an-5  ca-57  $^{1}$H-NMR:  I,  (ppm) - 8.28 (d, 2H, ArH), 8.12 (d, lH, ArH), 7.88 (t, lH, ArH), 7.80 (d, lH, ArH),  7.62-7.74 (m, 5H,ArH), 4.12(s, 2H, CH2), 2.31-2.43(m, lH, CH), 1.87-2.02(m, 2H, CH2), 1.49-1.68(m,  lH, CH), 1.27 (s, 9H, CH3), 0.85-1.15(m, 9H, CH3 + CH3 + CH3)  an-5  ca-58  $^{1}$H-NMR:  I,  (ppm) - 7.76-7.90 (m, 12H, ArH), 4.12(s, 2H, CH2), 1.87-2.69 (m, 12H, camphane + Ar---CH3 +  CH2 + CH), 1.49-1.72 (m, 2H, camphane + CH), 0.65-1.19 (m, 18H, CH3).  an-5  ca-59  $^{1}$H-NMR:  I,  (ppm) - 7.76-7.90 (m, 12H, ArH), 5.00 (s, lH, Hyper-lactone), 4.77 (s, 2H, Hyper-lactone),  4.27 (s, lH, Hyper-lactone), 4.12(s, 2H, CH2), 2.94 (s, lH, Hyper-lactone), 2.31-2.43(m, lH, CH),  1.49-2.13 (m, 19H, Hyper-lactone + CH3 + CH2 + CH), 0.85-1.15(m, 9H, CH3 + CH3 + CH3)  an-5  ca-60  $^{1}$H-NMR:  I,  (ppm) - 7.72-7.83(m, !OH, ArH), 7.59(s, 2H, ArH), 5.90(d, lH, CH), 4.87-5.05(m, 3H, CH),  4.62-4.68(m, 2H, CH2), 4.23(m, lH, CH), 4.12(s, 2H, CH2), 1.49-2.48(m, 12H, CH3 + CH2 +CH+ oxosultone),  0.85-1.15(m, 9H, CH3 + CH3 + CH3)  Component  Component  Component  Component  Component  (A)  (B)  (C)  (G)  (F)  Example 1  (A)-1  (B)-1  (C)-1  (F)-1  [100]  [11.5]  [1.74]  [2.5]  Example 2  (A)-1  (B)-1  (C)-2  (F)-1  [100]  [11.5]  [1.87]  [2.5]  Example 3  (A)-1  (B)-1  (C)-3  (F)-1  [100]  [11.5]  [2.04]  [2.5]  Example4  (A)-1  (B)-1  (C)-4  (F)-1  [100]  [11.5]  [2.47]  [2.5]  Component  (S)  (S)-1  (S)-2  [10.0]  [2900]  (S)-1  (S)-2  [10.0]  [2900]  (S)-1  (S)-2  [10.0]  [2900]  (S)-1  (S)-2  [10.0]  [2900] 