Arylsulfonic acid compound, use thereof, and method for producing arylsulfonic acid compound
Provided is an arylsulfonic acid compound characterized by being represented by formula (1). [In the formula, Ar 1 represents a group represented by formula (2) (in formula (2), R 1 to R 5 each independently represent a hydrogen atom, halogen atom, cyano group, nitro group, methyl group, or trifluoromethyl group; however, at least one of R 1 to R 5 represents a halogen atom) and Ar 2 represents a group represented by formula (3) or (4).]
1. An arylsulfonic acid compound, characterized by being represented by formula (1):
wherein Ar 1 represents a group represented by formula (2):
wherein R 1 to R 5 independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, a methyl group, or a trifluoromethyl group, provided that at least one of R 1 to R 5 represents a halogen atom, and
Ar 2 represents a group represented by formula (3) or (4):
2. The arylsulfonic acid compound of claim 1 , wherein Ar 2 represents a group represented by any one of formulas (3-1) and (3-2) and formulas (4-1) to (4-6):
3. The arylsulfonic acid compound of claim 1 or 2 , wherein at least one of R 1 to R 5 is a fluorine atom, and at least another one of R 1 to R 5 is a halogen atom, a nitro group, a cyano group or a trifluoromethyl group.
4. A dopant comprising the arylsulfonic acid compound of claim 1 .
5. A charge transport varnish comprising the dopant of claim 4 , a charge transport material, and an organic solvent.
6. A charge transport thin film obtained from baking the charge transport varnish of claim 5 .
7. An organic electroluminescent device comprising the charge transport thin film of claim 6 .
8. A method for producing a charge transport thin film, comprising the step of coating on a substrate and baking the charge transport varnish of claim 5 .
9. An arylsulfonic acid salt, characterized by being represented by formula (1′):
wherein Ar 1 represents a group represented by formula (2):
wherein R 1 to R 5 independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, a methyl group, or a trifluoromethyl group provided that at least one of R 1 to R 5 represents a halogen atom, and
Ar 3 represents a group represented by formula (3′) or (4′):
wherein M represents an alkali metal atom.
10. A method for producing the arylsulfonic acid salt of claim 9 , comprising the step of reacting an amine represented by formula (5) with an acid halide compound represented by formula (6):
wherein X represents a halogen atom, and
Ar 1 represents a group represented by formula (2):
wherein R 1 to R 5 independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, a methyl group, or a trifluoromethyl group, provided that at least one of R 1 to R 5 represents a halogen atom, and
Ar 3 represents a group represented by formula (3′) or (4′):
wherein M represents an alkali metal atom.
11. A method for producing the arylsulfonic acid compound of claim 1 , comprising the step of ion-exchange treatment of an arylsulfonic acid salt represented by formula (1′):
wherein Ar 1 represents a group represented by formula (2):
wherein R 1 to R 5 independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, a methyl group, or a trifluoromethyl group, provided that at least one of R 1 to R 5 represents a halogen atom, and
Ar 3 represents a group represented by formula (3′) or (4′):
wherein M represents an alkali metal atom.
12. A charge transport thin film comprising a dopant and a charge transport material,
wherein the dopant comprises an arylsulfonic acid compound represented by formula (1):
wherein Ar 1 represents a group represented by formula (2):
wherein R 1 to R 5 independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, a methyl group, or a trifluoromethyl group, provided that at least one of R 1 to R 5 represents a halogen atom, and
Ar 2 represents a group represented by formula (3) or (4):