40  US 9,164,383 B2  39  Table  3  shows the results of sensitivity, resolution, and  LWR of the resist compositions.  Basic Compound (Amine 1) and Crosslinkerofthe Following  Structural Formulae  TABLE 1  Coating Uniformity Test  Each resist composition in Tables 1 and 2 was coated onto  a 8-inch wafer and baked on a hot plate at 100°  C. for 60  seconds for evaporating off the solvent. Resist films of 40 nm  thick were formed in Examples 1 to 28 and Comparative  Examples 1, 2, 3 and 5 to 9, and a resist film of 60 nm thick  was formed in Comparative Example 4. Using an optical film  thickness measuring system, the thickness of a film was mea› sured in the plane of the 8-inch wafer. With respect to coating  uniformity, the film was rated OK when the difference  between maximum and minimum thickness measurements  was equal to or less than 2 nm, and NG when the difference  exceeded 2 nm. The results are shown in Table 3.  EB Writing Test  In the patterning test, the negative resist compositions pre› pared by filtering the solutions of Tables 1 and 2 through a  filter having a pore size of 0.2  µm  were used, and silicon  substrates having a diameter of 6 inches were vapor primed  with hexamethyldisilazane (HMDS). Using a coater/devel› oper system Clean Track Mark 5 (Tokyo Electron Ltd.), the  negative resist composition was spin coated onto the primed  silicon substrate and prebaked on a hot plate at 110°  C. for 60  seconds to form a resist film. The resist films in Examples 1 to  28 and Comparative Examples 5 to 9 had a thickness of 40  nm, and the resist film in Comparative Example 4 had a  thickness of 60 nm.  Using a system HL-800D (Hitachi, Ltd.), the resist film  was irradiated imagewise with EB at a HV voltage of 50 keV  in a vacuum chamber. The resist films of Comparative  Examples 1, 2 and 3 were not subjected to the exposure test  because the films had so poor coating uniformity that the  exposure test might lack reproducibility.  Using the system Clean Track Mark 5, immediately after  the imagewise exposure, the resist film was baked (PEB) at  the temperature shown in Table 3 for 60 seconds and puddle  developed with a 2.38 wt% TMAH aqueous solution for 20  seconds, yielding a negative pattern.  The pattern was evaluated as follows. Resolution was a  minimum size at the exposure dose (sensitivity) that provided  a 1: 1 resolution of a 100-nm line-and-space pattern. The  100-nm line-and-space pattern was measured for line width  roughness (LWR) under SEM.  Example  Resist 1  Example  Resist 2  Example  Resist 3  Example  Resist4  Example  Resist 5  Example  Resist 6  Example  Resist 7  Example  Resist  8  Example  Resist 9  Example  Resist 10  Example  Resist 11  Example  Resist 12  :::::~  Example  Resist 14  Example  Resist 15  Example  Resist 16  Example  Resist 17  Example  Resist 18  Example  Resist 19  Example  Resist 20  Example  Resist21  Example  Resist 22  Example  Resist 23  Example  Resist 24  Example  Resist 25  Example  Resist 26  Example  Resist 27  Example  Resist 28  Metal salt  (pbw)  magnesium L-pidolate(30)  Blending polymer 1(100)  magnesium stearate(30)  Blending polymer 1(100)  magnesium L-lactate hydrate(40)  Blending polymer 1(100)  magnesium monoethyl fumarate(40)  Blending polymer 1(100)  magnesium methacrylate(40)  Blending polymer 1(100)  hemi-magnesium L-aspartate  dihydrate(40) Blending polymer  1(100)  hemi-magnesium L-glutarnate  tetrahydrate(40) Blending polymer  1(100)  magnesium ethylbutyrate(40)  Blending polymer 1(100)  chromiwn cyclohexane› carboxylate( 40) Blending polymer  1 (100)  manganese 1-methylimidazole-4- carboxylate(40) Blending polymer  1(100)  iron oxocyclohexanecarboxylate(40)  Blending polymer 1(100)  cobalt cyclopentylacetate(40)  Blending polymer 1(100)  nickel propionate(40)  Blending polymer 1(100)  copper(!) pentanoate(40)  Blending polymer 1(100)  zinc 4-vinylbenzoate(40)  Blending polymer 1(100)  silver 1-pyrrolecarboxylate(40)  Blending polymer 1(100)  cadmium crotonate(40)  Blending polymer 1(100)  tin 4-fluorobenzeneacetate( 40)  Blending polymer 1(100)  indium ethylbutyrate(40)  Blending polymer 1(100)  hafnium carboxyethylacrylate(l00)  cesium pivalate(30)  Blending phenolic resin 1(70)  cesium pivalate(30)  Blending phenolic resin 2(70)  hafnium carboxyethylacrylate(50)  Blending silsesquioxane-titaniwn  oxide resin 1 (50)  hafnium carboxyethylacrylate(50)  Blending silsesquioxane-zirconiwn  oxide resin 1 (50)  hafnium carboxyethylacrylate(50)  Blending silsesquioxane-hafniwn  oxide resin 1 (50)  hafnium carboxyethylacrylate(50)  Blending silsesquioxane resin 1(50)  zirconium carboxyethylacrylate(l00)  antimony carboxyethylacrylate(l00)  Solvent  (pbw)  PGEE(5,000)  PGPE(5,000)  PGEE(5,000)  n-butanol(6,000)  n-butanol(5,000)  2-methyl-l› butanol(l,000)  isopropyl  alcohol(3,000)  water(2,000)  isopropyl  alcohol(3,000)  water(2,000)  n-butanol(5,000)  ally! alcohol(l ,000)  n-butanol(5,000)  furfuryl alcohol(l ,000)  PGEE(4,000)  tetrahydro furfury 1  alcohol (1,000)  PGME(4,000)  propargyl  alcohol(l ,000)  PGME(4,000)  ethyl lactate(l ,000)  PGEE(5,000)  PGEE(5,000)  PGEE(5,000)  PGEE(5,000)  PGEE(5,000)  PGEE(5,000)  PGEE(5,000)  n-butanol(6,000)  PGEE(5,000)  PGEE(5,000)  PGEE(4,000)  water(l ,000)  PGEE(4,000)  water(l ,000)  PGEE(4,000)  water(l ,000)  PGEE(4,000)  water(l ,000)  n-butanol(6,000)  n-butanol(6,000)  Amine 1  0  ’--...0/’--..N)lN/’--,.O/  H  /0..........._,,,NYN..........._,,,o-.....__  0  Crosslinker 