82  US 8,637,222  B2  81  (CL-1)  Examples 22 to 42  2.2 EUV Exposure  (3) Preparation and Coating of Negative Resist  Coating Solution  ( 4) Evaluation of EUV Exposure  The resist film obtained was subjected to surface exposure  using EUV light (wavelength: 13 nm) by changing the expo› sure dose in steps of0.5 mJ/cm 2  in the range from Oto 10.0  mJ/cm 2 .  This resist solution was applied on an HMDS-treated  6-inch Si wafer by using a spin coater, Mark 8, manufactured  by Tokyo Electron Ltd. and dried on a hot plate at 110°  C. for  90 seconds to obtain a 0.1 µm-thick  resist film.  The coating solution composition shown in Table 3 was  microfiltered through a membrane filter having a pore size of  0.1 µm  to obtain a resist solution.  After the irradiation, the resist film was heated on a hot  plate at 120°  C. for 90 seconds.  Subsequently, the resist film was spray-developed using  the organic solvent shown in Table 3 at a flow rate of 200  mL/min for 30 seconds and then dried by high-speed spinning  of2,000 revolutions (rpm) for 20 seconds.  In the case where an organic solvent is designated in the  column of Rinsing Solution of Table 3, after spray develop- ment using an organic solvent at a flow rate of200 mL/minfor  30 seconds, the resist film was rinsed with the designated  organic solvent at a flow rate of 200 mL/min for 30 seconds  while spinning the wafer by 1,500 revolutions (rpm) and then  dried by high-speed spinning of 2,000 revolutions (rpm) for  20 seconds.  Using the obtained sensitivity-residual film ratio curve, the  sensitivity (Eth) and the residual film ratio were evaluated by  the following methods.  The exposure dose when the residual film ratio becomes  50% was defined as the sensitivity (Eth).  The (film thickness after development/film thickness  before exposure )xl 00 at an irradiation dose three times larger  than the exposure dose giving the sensitivity (Eth) above was  defined as the residual film ratio(%).  In Table 3, the ratio when using two or more kinds of  components is the ratio by mass. The evaluation results are  shown in Table 4 below.  In Table 3, the abbreviations are the same as those in Table.  ( 4-1) Sensitivity (Eth)  (4-2) Residual Film Ratio  TABLE3  (B)  (C)Acid  Basic  Other  Surfac- Developer  Rinsing  Cross linking  Generator  Compound  Compo- Solvent  tant  (ratio  Solution  (A) Resin (mg)  Agent (mg)  (mg)  (mg)  nents (mg) (g)  (1mg)  by mass)  (ratio by mass)  Example 22  (29) Mw - 9200  MM-1 (120)  zll (50)  D-1 (2)  S-1 (10)  W-1  S-2  x/y- 80/20  Mw/Mn - 2.0 (400 mg)  Example 23  (2) Mw -5000  MM-1 (180)  z39 (50)  D-1 (2)  S-1/S-2  W-1  S-7  Mw/Mn - 1.18 (340 mg)  (8/2)  Example 24  (1) Mw-2500  MM-2(110)  z2 (50)  D-4 (3)  S-1 (10)  W-1  S-1/S-2  Mw/Mn- 1.15 (400 mg)  (30/70)  Example 25  (2) Mw -7000  MM-3 (120)  z8 (50)  D-1 (4)  S-1 (10)  W-2  S-1/S-2  Mw/Mn - 1.3 (400 mg)  (30/70)  Example 26  (27) Mw - 3500  MM-1 (120)  z45 (50)  D-2 (2)  S-1/S-2  W-1  S-8  x/y- 85/15  (8/2)  Mw/Mn - 1.2 (400 mg)  Example 27  (25) Mw - 5000  MM-3 (180)  z56 (50)  D-3 (6)  S-2 (10)  W-1  S-9  x/y- 60/40  Mw/Mn - 1.1 (340 mg)  Example 28  (32) Mw - 7500  MM-1 (120)  z81 (50)  D-1 (1)  F-1 (12)  S-1/S-2  W-2  S-3  x/y- 80/20  (8/2)  Mw/Mn - 1.6 (400 mg)  Example 29  (2) Mw -5000  CL-1 (120)  z85 (60)  D-1 (2)  F-2 (12)  S-1 (10)  W-1  S-4  Mw/Mn- 1.18 (400 mg)  Example 30  (2) Mw -5000  MM-1 (120)  zll (50)  D-1 (2)  S-1/S-2  W-1  S-4  Mw/Mn - 1.1 (300 mg)/  (8/2)  (1) Mw-2500  Mw/Mn - 1.1 (100 mg)  Example 31  (58) Mw - 3500 x/y- 80/20  MM-1 (120)  zll (60)  D-2 (2)  S-1/S-2  W-1  S-4  Mw/Mn - 2.0 (400 mg)  (8/2)  Example 32  (2) Mw -5000  MM-1 (120)  z81 (50)  D-2 (2)  S-1/S-2  W-1  S-2  S-5  Mw/Mn- 1.18 (400 mg)  (8/2)  Example 33  P-1 Mw - 5000 x/y - 40/60  X-1 (120)  z59 (50)  D-1 (1)  S-1 (10)  W-1  S-4  S-5  Mw/Mn - 1.5 (400 mg)  Example 34  P-1 Mw - 5000 x/y - 40/60  X-2 (120)  z59 (50)  D-1 (1)  S-1 (10)  W-1  S-4  S-5  Mw/Mn - 1.5 (400 mg)  Example 35  P-1 Mw - 5000 x/y - 40/60  X-3 (120)  z59 (50)  D-1 (2)  S-1 (10)  W-1  S-4  S-5  Mw/Mn - 1.5 (400 mg)  -continued 