Organometallic compound comprising a metal combined with at least one ligand containing four or more fluorine atoms, resist composition comprising the same, and method of fabricating semiconductor device using the same
A resist material is combined with a ligand containing four or more fluorine atoms and is represented by the following formula: [(R 1 M) i O j X k (OH) m ] (OH) n R 2 p , wherein one of “R 1 ” and “R 2 ” is C a F b H c , C a F b H c N d , C a F b H c P d , C a F b H c S d , C a F b H c O d , C a F b H c N d S e , C a F b H c P d S e , C a F b H c N d O e , or C a F b H c P d O e , the other of “R 1 ” and “R 2 ” is C a H c , C a F b H c , C a F b H c N d , C a F b H c P d , C a F b H c S d , C a F b H c O d , C a F b H c N d S e , C a F b H c P d S e , C a F b H c N d O e , or C a F b H c P d O e , “a” and “c” are each independently an integer of 0 to 20, “b” is an integer of 4 to 30, “d” and “e” are each independently an integer of 0 to 5, “M” is one metal selected from a specified list, “i” is an integer from 1 to 12, “j” is an integer of 1 to 14, “X” is a halogen selected from a specified list, “k” and “m” are each independently an integer of 0 to 6, and “n” and “p” are each independently an integer of 0 to 2.
1 . An organometallic compound comprising a metal combined with at least one ligand comprising four or more fluorine atoms, wherein the organometallic compound has one structure selected from the following Chemical Formulas 2 to 5:
wherein
one of R 1 and R 2 is C a F b H c , C a F b H c N d , C a F b H c P d , C a F b H c S d , C a F b H c O d , C a F b H c N d S e , C a F b H c P d S e , C a F b H c N d O e , or C a F b H c P d O e ,
the other of R 1 and R 2 is C a H c , C a F b H c , C a F b H c N d , C a F b H c P d , C a F b H c S d , C a F b H c O d , C a F b H c N d S e , C a F b H c P d S e , C a F b H c N d O e , or C a F b H c P d O e ,
a is an integer of 1 to 20,
d and e are each independently an integer of 0 to 5,
c is an integer of 0 to 20, provided that c is an integer of 3 to 20 for C a H c as the other of R 1 and R 2 ,
and
b is an integer of 4 to 30.
2 . The organometallic compound of claim 1 , wherein the organometallic compound has a cage shape.
3 . The organometallic compound of claim 1 , wherein R 1 has one structure selected from
and
wherein R 2 has a structure of
4 . The organometallic compound of claim 1 , wherein the organometallic compound has a structure represented by Chemical Formula 2:
5 . A resist composition comprising:
an organometallic compound; and
an organic solvent,
wherein the organometallic compound has a structure selected from the following Chemical Formulas 2 to 5:
(Chemical Formula 2)
wherein:
one of R 1 and R 2 is C a F b H c , C a F b H c N d , C a F b H c P d , C a F b H c S d , C a F b H c O d , C a F b H c N d S e , C a F b H c P d S e , C a F b H c N d O e , or C a F b H c P d O e ,
the other of R 1 and R 2 is C a H c , C a F b H c , C a F b H c N d , C a F b H c P d , C a F b H c S d , C a F b H c O d , C a F b H c N d S e , C a F b H c P d S e , C a F b H c N d O e , or C a F b H c P d O e ,
a is an integer of 1 to 20,
d and e are each independently an integer of 0 to 5,
c is an integer of 0 to 20, provided that c is an integer of 3 to 20 for C a H c as the other of R 1 and R 2 ,
and
b is an integer of 4 to 30.
6 . The resist composition of claim 5 , wherein the organometallic compound has a cage shape.
7 . The resist composition of claim 5 , wherein R 1 has one structure selected from
and
wherein R 2 has a structure of
8 . The resist composition of claim 5 , wherein the resist composition comprises the organometallic compound in an amount of 1 to 30 wt. % based on a total weight of the resist composition, and
wherein the resist composition comprises the organic solvent in an amount of 70 to 99 wt. % based on the total weight of the resist composition.
9 . The resist composition of claim 5 , wherein the organic solvent is at least one of methyl isobutyl carbinol (MIBC), ether, propylene glycol monomethyl ether acetate (PGMEA), propylene glycol monomethyl ether (PGME), ethyl lactate (EL), P-hydroxy P-methylbutyric acid (HBM) or a fluorine-containing material.
10 . The resist composition of claim 5 , further comprising at least one of a photo acid generator, a radical quencher, a photolysis quencher, a thermal acid generator, surfactant, and a base quencher in an amount of 0 to 10 wt. % based on a total weight of the resist composition.
11 . The resist composition of claim 5 , wherein the organometallic compound has a structure represented by Chemical Formula 2:
12 . A method of fabricating a semiconductor device, the method comprising:
preparing a resist composition including an organometallic compound and an organic solvent;
coating the resist composition on a substrate to form a resist layer;
performing a soft bake process to evaporate the organic solvent;
performing an exposure process and a post-bake process to change a portion of the resist layer into a mask pattern; and
performing a development process to remove the resist layer while retaining the mask pattern,
wherein the organometallic compound has a structure selected from the following Chemical Formulas 2 to 5:
(Chemical Formula 2)
wherein:
one of R 1 and R 2 is C a F b H c , C a F b H c N d , C a F b H c P d , C a F b H c S d , C a F b H c O d , C a F b H c N d S e , C a F b H c P d S e , C a F b H c N d O e , or C a F b H c P d O e ,
the other of R 1 and R 2 is C a H c , C a F b H c , C a F b H c N d , C a F b H c P d , C a F b H c S d , C a F b H c O d , C a F b H c N d S e , C a F b H c P d S e , C a F b H c N d O e , or C a F b H c P d O e ,
a is an integer of 1 to 20,
d and e are each independently an integer of 0 to 5,
c is an integer of 0 to 20, provided that c is an integer of 3 to 20 for C a H e as the other of R 1 and R 2 ,
and
b is an integer of 4 to 30.
13 . The method of claim 12 , wherein the development process comprises developing with a developer comprising fluorine.
14 . The method of claim 12 , wherein the organometallic compound has a cage shape.
15 . The method of claim 12 , wherein R 1 has one structure selected from
wherein R 2 has a structure of
16 . The method of claim 12 , wherein the resist composition comprises the organometallic compound in an amount of 1 to 30 wt. % based on a total weight of the resist composition, and
wherein the resist composition comprises the organic solvent in an amount of 70 to 99 wt. % based on the total weight of the resist composition.
17 . The method of claim 12 , wherein the organic solvent is at least one of methyl isobutyl carbinol (MIBC), ether, propylene glycol monomethyl ether acetate (PGMEA), propylene glycol monomethyl ether (PGME), ethyl lactate (EL), P-hydroxy P-methylbutyric acid (HBM) or a fluorine-containing material.
18 . The method of claim 12 , wherein the resist composition further comprises at least one of a photo acid generator, a radical quencher, a photolysis quencher, a thermal acid generator, surfactant, and a base quencher in an amount of 0 to 10 wt. % based on a total weight of the resist composition.
19 . The method of claim 12 , wherein, in the exposure process and the post-bake process, a radical combination between organometallic compounds occurs in a portion of the resist layer to increase molecular weight.
20 . The method of claim 12 , wherein the organometallic compound has a structure represented by Chemical Formula 2: