Fluorine-containing aromatic compound and manufacturing method therefor

1. A method comprising:

reacting a compound represented by the following formula (1) with a compound represented by the formula Rf 1 X 1 in a halogen-containing solvent in the presence of a thiosulfate salt under light irradiation; and

heating a resultant obtained in the reacting step,

thereby obtaining a fluorine-containing aromatic compound represented by the following formula (2-1):

[R is a hydrogen atom, an alkyl group having a carbon number of 2 to 12 which may have a substituent other than a fluorine atom, or a monovalent aromatic group which may have a substituent;

Rf 1 is a fluorine-containing alkyl group having a carbon number of 1 to 12 which may have a substituent;

X 1 represents an iodine atom or a bromine atom; and

m is an integer of 1 or more, n is an integer of 0 or more and m+n is an integer of 1 or more and 5 or less].

2. The method according to claim 1 , wherein R is a hydrogen atom or an unsubstituted alkyl group having a carbon number of 2 to 12.

3. The method according to claim 1 , wherein in the formula (2-1), Rf 1 is a perfluoroalkyl group having a carbon number of 1 to 6.

4. The method according to claim 1 , wherein the compound represented by the formula (2-1) is a compound represented by the following formula (3-1):

[Rf 1 and R represent the same meanings as mentioned above].

5. The method according to claim 1 , wherein the compound represented by the formula (2-1) is a compound represented by the following formula (4-1):

[Rf 1 and R represent the same meanings as mentioned above].

6. The method according to claim 1 , wherein the wavelength of the irradiation light is from 300 to 600 nm.

7. The method according to claim 1 , wherein the heating temperature is from 200 to 300° C.

8. A method comprising:

obtaining the compound represented by the following formula (2-1) by the method as defined in claim 1 ; and

obtaining an organic semiconductor material comprising the compound represented by the following formula (2-1),

wherein contents of metals of Ni, Cu, Zn, and Pd in the organic semiconductor material are each 1 ppm by mass or less and total content of metals in the organic semiconductor material is 10 ppm by mass or less:

[Rf 1 , R, m and n represent the same meanings as mentioned above].

9. A method comprising:

reacting a compound represented by the following formula (1-1) with a compound represented by the formula Rf 1 X 1 in a halogen-containing solvent in the presence of a thiosulfate salt under light irradiation to obtain a compound represented by the following formula (1-1′);

heating the compound represented by the formula (1-1′) to obtain a fluorine-containing aromatic compound represented by the following formula (2-1-1);

reacting the compound represented by the formula (2-1-1) with a compound represented by the formula Rf 2 X 2 in a halogen-containing solvent in the presence of a thiosulfate salt under light irradiation; and

heating a resultant obtained in the reacting step of the compound represented by the formula (2-1-1),

thereby obtaining a fluorine-containing aromatic compound represented by the following formula (2-2):

[Rf 1 and Rf 2 are a fluorine-containing alkyl group having a carbon number of 1 to 12 which may have a substituent and Rf 1 and Rf 2 may be the same or different;

X 1 and X 2 represent an iodine atom or a bromine atom and may be the same or different; and

m is an integer of 1 or more, n is an integer of 0 or more and m+n is an integer of 1 or more and 5 or less].

10. The method according to claim 9 , wherein Rf 1 and Rf 2 may be the same or different, and Rf 1 is a fluorine-containing alkyl group having a carbon number of 1 to 12 which may have a substituent and Rf 2 is a fluorine-containing alkyl group having a carbon number of 4 to 7 which may have a substituent.

11. The method according to claim 9 , wherein in the formula (2-2), Rf 1 and Rf 2 may be the same or different, and Rf 1 is a perfluoroalkyl group having a carbon number of 1 to 12 and Rf 2 is a perfluoroalkyl group having a carbon number of 4 to 7.

12. The method according to claim 9 , wherein the compound represented by the formula (2-2) is a compound represented by the following formula (3-2):

[Rf 1 and Rf 2 represent the same meanings as mentioned above].

13. The method according to claim 12 , wherein in the formula (3-2), Rf 1 and Rf 2 may be the same or different, and Rf 1 is a perfluoroalkyl group having a carbon number of 1 to 12 and Rf 2 is a perfluoroalkyl group having a carbon number of 4 to 7.

14. The method according to claim 9 , wherein the compound represented by the formula (2-2) is a compound represented by the following formula (4-2):

[Rf 1 and Rf 2 represent the same meanings as mentioned above].

15. The method according to claim 14 , wherein in the formula (4-2), Rf 1 and Rf 2 may be the same or different, and Rf 1 is a perfluoroalkyl group having a carbon number of 4 to 7 and Rf 2 is a perfluoroalkyl group having a carbon number of 1 to 12.

16. The method according to claim 9 , wherein the wavelength of the irradiation light is from 300 to 600 nm.

17. The method according to claim 9 , wherein the heating temperature is from 200 to 300° C.

18. A method comprising:

obtaining the compound represented by the following formula (2-2) by the method as defined in claim 9 ; and

obtaining an organic semiconductor material comprising the compound represented by the following formula (2-2),

wherein contents of metals of Ni, Cu, Zn, and Pd in the organic semiconductor material are each 1 ppm by mass or less and total content of metals in the organic semiconductor material is 10 ppm by mass or less:

[Rf 1 , Rf 2 , m and n represent the same meanings as mentioned above].