Aniline derivatives and uses thereof
Aniline derivatives such as those represented by the formula shown, for example, have good solubility with respect to organic solvents, and are able to provide an organic electroluminescent element having excellent luminance characteristics when a thin film containing said aniline derivatives is used as a charge transporting substance in a hole injection layer. (In the formula, DPA represents a diphenylamino group.)
1. An aniline derivative represented by the formula (1) or (2):
wherein R 1 and R 2 independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, or an alkyl group having 1 to 20 carbon atoms, alkenyl group having 2 to 20 carbon atoms, alkynyl group having 2 to 20 carbon atoms, aryl group having 6 to 20 carbon atoms or heteroaryl group having 2 to 20 carbon atoms which may be substituted with a halogen atom,
Ph 1 represents a group represented by the formula (P1):
wherein R 3 to R 6 independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, or an alkyl group having 1 to 20 carbon atoms, alkenyl group having 2 to 20 carbon atoms, alkynyl group having 2 to 20 carbon atoms, aryl group having 6 to 20 carbon atoms or heteroaryl group having 2 to 20 carbon atoms which may be substituted with a halogen atom,
Ar 1 independently represents a group represented by any of the formulas (B1) to (B11):
wherein R 7 to R 27 , R 30 to R 51 and R 53 to R 154 independently represent a hydrogen atom, a halogen atom, a nitro group, a cyano group, or a diphenylamino group, alkyl group having 1 to 20 carbon atoms, alkenyl group having 2 to 20 carbon atoms, alkynyl group having 2 to 20 carbon atoms, aryl group having 6 to 20 carbon atoms or heteroaryl group having 2 to 20 carbon atoms which may be substituted with a halogen atom,
R 28 and R 29 independently represent an aryl group having 6 to 20 carbon atoms or heteroaryl group having 2 to 20 carbon atoms which may be substituted with Z 1 ,
R 52 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, alkenyl group having 2 to 20 carbon atoms or alkynyl group having 2 to 20 carbon atoms which may be substituted with Z 4 , or an aryl group having 6 to 20 carbon atoms or heteroaryl group having 2 to 20 carbon atoms which may be substituted with Z 1 ,
Ar 4 independently represents an aryl group having 6 to 20 carbon atoms which may be substituted with a di(aryl groups having 6 to 20 carbon atoms)amino group,
Z 1 represents a halogen atom, a nitro group, a cyano group, or an alkyl group having 1 to 20 carbon atoms, alkenyl group having 2 to 20 carbon atoms or alkynyl group having 2 to 20 carbon atoms which may be substituted with Z 2 ,
Z 2 represents a halogen atom, a nitro group, a cyano group, or an aryl group having 6 to 20 carbon atoms or heteroaryl group having 2 to 20 carbon atoms which may be substituted with Z 3 ,
Z 3 represents a halogen atom, a nitro group or a cyano group,
Z 4 represents a halogen atom, a nitro group, a cyano group, or an aryl group having 6 to 20 carbon atoms or heteroaryl group having 2 to 20 carbon atoms which may be substituted with Z 5 , and
Z 5 represents a halogen atom, a nitro group, a cyano group, or an alkyl group having 1 to 20 carbon atoms, alkenyl group having 2 to 20 carbon atoms or alkynyl group having 2 to 20 carbon atoms which may be substituted with Z 3 ,
Ar 2 independently represents a group represented by any of the formulas (A1) to (A5) or (A7) to (A12) or (A14) to (A18):
wherein R 155 represents an hydrogen atom or an alkyl group having 1 to 20 carbon atoms, alkenyl group having 2 to 20 carbon atoms or alkynyl group having 2 to 20 carbon atoms which may be substituted with Z 4 , or an aryl group having 6 to 20 carbon atoms or heteroaryl group having 2 to 20 carbon atoms which may be substituted with Z 1 ,
R 156 and R 157 independently represent an aryl group having 6 to 20 carbon atoms or heteroaryl group having 2 to 20 carbon atoms which may be substituted with Z 1 ,
DPA represents a diphenylamino group, and
Ar 4 , Z 1 and Z 3 to Z 5 have the same meanings as above,
Ar 3 represents a group represented by any of the formulas (C2) to (C8):
letter k represents an integer of 1 to 10, and
letter l represents 1 or 2.
2. The aniline derivative of claim 1 ,
wherein Ar 1 is a group represented by any of the formulas (B1′) to (B11′):
wherein R 7 to R 154 and Ar 4 have the same meanings as above, and
Ar 3 is a group represented by any of the formulas (C2′) to (C8′):
wherein DPA has the same meaning as above.
3. The aniline derivative of claim 1 or 2 , wherein the R 3 to R 6 , R 7 to R 27 , R 30 to R 51 and R 53 to R 154 are each a hydrogen atom.
4. The aniline derivative of claim 1 , represented by the formula (1-1):
wherein Ar 5 simultaneously represent a group represented by any of the formulas (D1), (D2), (D4) to (D9), or (D11) to (D13), and Ph 1 and letter k have the same meanings as above:
wherein R 52 , R 156 , R 157 , A 4 and DPA have the same meanings as above.
5. The aniline derivative of claim 1 , represented by the formula (1-3), (1-4), (1-9) or (1-10):
wherein Ar 51 represents a group represented by the formula (F1-1), Ar 52 represents a group represented by the formula (F2-1), Ar 71 represents a group represented by the formula (F2-2), Ar 72 represents a group represented by the formula (F1-2), and Ph 1 , Ar 1 and letter k have the same meanings as above:
wherein Cb 155 represents an alkyl group having 1 to 20 carbon atoms, alkenyl group having 2 to 20 carbon atoms or alkynyl group having 2 to 20 carbon atoms which may be substituted with Z 4 , or an aryl group having 6 to 20 carbon atoms or heteroaryl group having 2 to 20 carbon atoms which may be substituted with Z 1 , and Z 1 , Z 4 and Ar 4 have the same meanings as above.
6. The aniline derivative of claim 1 , represented by the formula (1-5), (1-6), (1-11) or (1-12):
wherein Ar 51 represents a group represented by the formula (F1-1), Ar 52 represents a group represented by the formula (F2-1), Ar 71 represents a group represented by the formula (F2-2), Ar 72 represents a group represented by the formula (F1-2), and Ph 1 and letter k have the same meanings as above:
wherein Cb 155 represents an alkyl group having 1 to 20 carbon atoms, alkenyl group having 2 to 20 carbon atoms or alkynyl group having 2 to 20 carbon atoms which may be substituted with Z 4 , or an aryl group having 6 to 20 carbon atoms or heteroaryl group having 2 to 20 carbon atoms which may be substituted with Z 1 , and Z 1 , Z 4 and Ar 4 have the same meanings as above.
7. A charge transporting substance comprising the aniline derivative of claim 1 .
8. A charge transporting material comprising the charge transporting substance of claim 7 .
9. A charge transporting varnish comprising the charge transporting substance of claim 7 and an organic solvent.
10. The charge transporting varnish of claim 9 , further comprising a dopant substance.
11. The charge transporting varnish of claim 10 , wherein the dopant substance includes at least one selected from halotetracyanoquinodimethanes and benzoquinone derivatives.
12. The charge transporting varnish of claim 11 , wherein the dopant substance further includes a heteropoly-acid compound.
13. The charge transporting varnish of claim 9 , further comprising an organic silane compound.
14. A charge transporting thin film produced by use of the charge transporting varnish of claim 9 .
15. A charge transporting thin film produced by a vapor deposition method using the aniline derivative of claim 1 .
16. An organic electroluminescence element comprising the charge transporting thin film of claim 14 or 15 .
17. An organic electroluminescence element of claim 16 , wherein the charge transporting thin film is a hole injection layer, a hole transport layer or a hole injection transport layer.