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

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: