US 10,394,127 B2  108  107  -continued  DR-5: Undecane  DR-6: Decane  DR-7: Methyl isobutyl carbinol (MIBC=4-methyl-2-pen› tanol)  DR-8: Pure water  Examples 1 to 35 and Comparative Example 1  (Extreme Ultraviolet (EUV) Exposure and Organic  Solvent Development)  <Preparation of Resist Composition>  The components shown in Tables 2 and 3 below were  dissolved in a solvent, and each of the solutions was filtered  through a polyethylene filter having a pore size of 0.03 µm  to prepare resist compositions of Examples 1 to 35 and  Comparative Example 1. Further, in Tables 2 and 3, the  amounts in parts by mass of the respective components and  solvent in are shown.  <Formation of Resist Film, Pattern Formation, and Devel› opment>  An organic antireflection film ARC29SR (manufactured  by Nissan Chemical Industries, Ltd.) was applied onto a  silicon wafer, and baking was carried out at 205°  C. for 60  seconds to form an antireflection film having a film thick- ness of 86 nm. Each of the resist compositions prepared  above was applied thereonto, and baking (PB) was carried  out at 120°  C. for 60 seconds to form a resist film having a  film thickness of 50 nm. The wafer having the resist film  applied thereon was subjected to pattern exposure with an  exposure mask (line/space=l/1), using an EUV exposure  device (Micro Exposure Tool manufactured by Exitech, NA  0.3, Quadrupole, outer sigma 0.68, inner sigma 0.36). After  irradiation, heating was carried out at 120° C. for 60  seconds, development was then carried out by paddling for  30 seconds using a developer on a hot plate, the wafer was  rotated at a rotation speed of 2,000 rpm for 30 seconds, and  baking was carried out at 100°  C. for 60 seconds to obtain  a 1: 1 line-and-space pattern having a line width of 20 nm.  Comparative Example 2 (Extreme Ultraviolet  (EUV) Exposure) and Alkali Development  In the same manner as in Comparative Example 1 except  that the composition was changed as shown in Table 2  below, and thus, development was carried out with an  aqueous alkali solution (TMAH; 2.38%-by-mass aqueous  tetramethylammonium hydroxide solution) instead of the  organic developer, and water was used as a rinsing liquid, a  resist composition was prepared and pattern formation was  carried out.  As the surfactant, the following compounds were used.  Wl: MEGAFACE Fl 76 (manufactured by DIC Corpora› tion) (fluorine-based)  W2: MEGAFACE ROS (manufactured by DIC Corpora› tion) (fluorine- and silicon-based)  W3: Polysiloxane Polymer KP-341 (manufactured by  Shin-Etsu Chemical Co., Ltd.) (silicon-based)  W4: TROYSOL S-366 (manufactured by Troy Chemical  Corporation)  W5: KH-20 (manufactured by Asahi Glass Co., Ltd.)  W6:  POLYFOXTfM  PF-6320  (manufactured  by  OMNOVA solution inc.) (fluorine-based)  As the solvent, the following ones were used.  Group a  SL-1: Propylene glycol monomethyl ether acetate (PG- MEA)  SL-2: Propylene glycol monomethyl ether propionate  SL-3: 2-Heptanone  Group b  SL-5: Propylene glycol monomethyl ether (PGME)  SL-4: Ethyl lactate  SL-6: Cyclohexanone  Group c  SL-7: y-Butyrolactone  As the developer and the rinsing liquid, the following  ones were used.  DR-1: 3-Methylbutyl acetate  DR-2: Butyl acetate  DR-3: Methyl amyl ketone (MAK)  DR-4: 2.38%-by-mass aqueous tetramethylammonium  hydroxide solution  TABLE 2  Resin (A)  Acid generator  Basic com12ound  Surfactant  Solvent  Parts  Parts  Parts  Parts  Parts  Compound  by Compound  by Compound  by  Compound  by Compound  by  Nos.  mass Nos.  mass Nos.  mass  Nos.  mass Nos.  mass  Developer Rinsing  Example  1 A-1  42  B-1  7  C-1  SL-1/SL-2  2,200/250 DR-1  DR-5  Example  2 A-2  43  B-3  6  C-5  SL-1/SL-2  2,200/250 DR-1  DR-5  Example  3 A-4  41  B-3  8  C-1  Wl  1  SL-1/SL-3  2,000/450 DR-1  DR-5  Example  4 A-3  41  B-4  8  C-1  SL-1/SL-6  2,000/450 DR-1  DR-5  Example  5 A-2  40  B-1  9  C-1  SL-1/SL-2  2,200/250 DR-1  DR-5  Example  6 A-11  44  B-5  5  C-1  W2  1  SL-1/SL-2  2,200/250 DR-1  DR-5  Example  7 A-7  43  B-4  6  C-4  SL-1/SL-2/  2,200/150/ DR-1  DR-5  SL-5  250  Example  8 A-8  42  B-2  7  C-5  SL-1/SL-2  2,200/250 DR-1  DR-5  Example  9 A-5  44  B-6  5  C-2  W6  1  SL-1/SL-4  2,100/350 DR-1  DR-5  Example  10 A-5  39  B-1  10  C-1  SL-1/SL-2  2,200/250 DR-1  DR-5  C-6  C-5 