150  149  US  9,104,101 B2  Examples of phosphinic acid derivatives phosphinic acid  esters such as phenylphosphinic acid.  As the component (E), salicylic acid is particularly pre› ferred.  As the component (E), one compound may be used alone,  or two or more different compounds may be used in combi› nation.  The component (E) is typically used in an amount within a  range from 0.01 to 5.0 parts by weight relative to 100 parts by  weight of the combination of the component (A) and the  component (C) (or relative to 100 parts by weight of the  component (A) in those cases where the composition does not  include the component (C)).  If desired, miscible additives may also be added to the  resist composition of the present invention. Examples of such  miscible additives include additive resins for improving the  performance of the resist film, surfactants for improving the  applicability, dissolution inhibitors, plasticizers, stabilizers,  colorants, halation prevention agents, and dyes.  Specific examples of the alkyl alcohol amine include  diethanolamine, triethanolamine, diisopropanolamine, triiso› propanolamine,  di-n-octanolamine,  tri-n-octanolamine,  stearyldiethanolamine and lauryldiethanolamine.  Examples of the cyclic amine include heterocyclic com- pounds containing a nitrogen atom as a hetero atom. The  heterocyclic compound may be a monocyclic compound ( ali› phatic monocyclic amine) or a polycyclic compound (ali› phatic polycyclic amine).  Specific examples of the aliphatic monocyclic amine  include piperidine and piperazine.  The aliphatic polycyclic amine preferably has 6 to 10 car› bon atoms, and specific examples include 1,5-diazabicyclo  [ 4.3.0]-5-nonene, 1,8-diazabicyclo[5.4.0]-7-undecene, hex- amethylenetetramine and 1,4-diazabicyclo[2.2.2]octane.  Examples of other aliphatic amines include tris(2-meth› oxymethoxyethyl)amine,  tris{ 2-(2-methoxyethoxy)  ethyl }amine,  tris{ 2-(2-methoxyethoxymethoxy)  ethyl }amine, tris{ 2-(1-methoxyethoxy)ethyl}amine, tris{ 2- (1-ethoxyethoxy)ethyl }amine,  tris{ 2-(1-ethoxypropoxy)  ethyl }amine and tris[2-{ 2-(2-hydroxyethoxy)ethoxy }ethyl]  amme.  The resist composition of the present invention can be  prepared by dissolving the materials for the resist composi› tion in an organic solvent (hereinafter frequently referred to  as "component (S)").  The component (S) may be any organic solvent which can  dissolve each of the components used to give a uniform solu› tion, and one or more types of organic solvent may be selected  appropriately from those solvents that have been convention› ally known as solvents for a chemically amplified resists.  Examples include lactones such as y-butyrolactone;  ketones such as acetone, methyl ethyl ketone, cyclohex› anone, methyl-n-pentyl ketone, methyl isopentyl ketone and  2-heptanone;  polyhydric alcohols such as ethylene glycol, diethylene  glycol, propylene glycol and dipropylene glycol;  Examples of the aromatic amine include aniline, pyridine,  4-dimethylaminopyridine, pyrrole, indole, pyrazole, imida› zole and derivatives thereof, diphenylamine, triphenylamine,  tribenzy !amine, 2, 6-diisopropylaniline and N-tert-butoxycar› bonyl pyrrolidine.  As the component (D), any of the above compounds may  be used alone, or two or more different compounds may be 30  used in combination.  The component (D) is typically used in an amount within a  range from 0.01 to 5.0parts by weight, relative to l00parts by  weight of the combination of the component (A) and the  component (C) (or relative to 100 parts by weight of the  component (A) in those cases where the composition does not  include the component (C)). By ensuring that the amount of  the component (D) is within the aforementioned range, the  shape of the resist pattern and the post exposure stability of  the latent image formed by the pattern-wise exposure of the  resist layer are improved.  polyhydric alcohol derivatives, including compounds hav- ing an ester bond such as ethylene glycol monoacetate, dieth› ylene glycol monoacetate, propylene glycol monoacetate and  dipropylene glycol monoacetate, and compounds having an  ether bond, such as a monoalky I ether ( such as a monomethy I  ether, monoethyl ether, monopropyl ether or monobutyl  ether) or a monophenyl ether of any of these polyhydric  alcohols or compounds having an ester bond [ among these  derivatives, propylene glycol monomethyl ether acetate (PG› MEA) and propylene glycol monomethyl ether (PGME) are  preferred];  Furthermore, in the resist composition of the present inven› tion, for the purposes of preventing any deterioration in sen› sitivity, and improving the resist pattern shape and the post  exposure stability of the latent image formed by the pattern› wise exposure of the resist layer, at least one compound (E)  (hereinafter referred to as "component (E)") selected from the  group consisting of organic carboxylic acids, and phosphorus  oxo acids and derivatives thereof may also be added.  cyclic ethers such as dioxane;  esters such as methyl lactate, ethyl lactate (EL), methyl  acetate, ethyl acetate, butyl acetate, methyl pyruvate, ethyl  pyruvate, methyl methoxypropionate and ethyl ethoxypropi- onate; and  Examples of the organic carboxylic acids include acetic  acid, malonic acid, citric acid, malic acid, succinic acid, ben› zoic acid and salicylic acid.  Examples of the phosphorus oxo acids include phosphoric  acid, phosphonic acid and phosphinic acid. Among these,  phosphonic acid is particularly desirable.  aromatic organic solvents such as anisole, ethyl benzyl  ether, cresyl methyl ether, diphenyl ether, dibenzyl ether,  phenetole, butyl phenyl ether, ethylbenzene, diethylbenzene,  pentylbenzene, isopropylbenzene, toluene, xylene, cymene  and mesitylene.  Examples of the phosphorus oxo acid derivatives include  esters in which a hydrogen atom within an aforementioned  oxo acid is substituted with a hydrocarbon group. Examples  of the hydrocarbon group include alkyl groups of 1 to 5  carbon atoms and aryl groups of 6 to 15 carbon atoms.  Examples of phosphoric acid derivatives include phos› phate esters such as di-n-butyl phosphate and diphenyl phos› phate.  These organic solvents may be used individually, or as a  mixed solvent containing two or more solvents.  Among the above solvents, propylene glycol monomethyl  ether acetate (PGMEA), propylene glycol monomethyl ether  (PGME) and ethyl lactate (EL) are preferred.  Further, among the mixed solvents, a mixed solvent  obtained by mixing PGMEA with a polar solvent is prefer› able. The mixing ratio (weight ratio) of the mixed solvent may  be determined as appropriate, with due consideration of the  compatibility of the PGMEA with the polar solvent, but is  preferably within a range from  1:  9 to 9: 1, and more preferably  from 2:8 to 8:2. For example, when EL is mixed as the polar  Examples of phosphonic acid derivatives include phospho› nate esters such as dimethyl phosphonate, di-n-butyl phos› phonate, phenylphosphonic acid, diphenyl phosphonate and  dibenzyl phosphonate. 