AZAAZENE ANALOGUES AND THEIR USE AS SEMICONDUCTOR

Abstract

The present invention provides compounds of formula (1) and an electronic device comprising the compounds as semiconducting material.

##STR00001##

Claims

1.-10. (canceled)

11. A compound of formula ##STR00027## wherein R.sup.1 and R.sup.2 are independently from each other selected from the group consisting of H, C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-8-cycloalkyl, C.sub.5-8-cycloalkenyl, 5 to 14 membered heterocycloalkyl, 5 to 14 membered heterocycloalkenyl, C.sub.6-14-aryl and 5 to 14 membered heteroaryl, and R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 are independently from each other selected from the group consisting of H, C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-8-cycloalkyl, C.sub.5-8-cycloalkenyl, 5 to 14 membered heterocycloalkyl, 5 to 14 membered heterocycloalkenyl, C.sub.6-14-aryl, 5 to 14 membered heteroaryl, halogen, CN, SCN, NO.sub.2, OH, OC.sub.1-30-alkyl, OC.sub.2-30-alkenyl, OC.sub.2-30-alkynyl, OC.sub.5-8-cycloalkyl, OC.sub.5-8-cycloalkenyl, O-5 to 14 membered heterocycloalkyl, O-5 to 14 membered heterocycloalkenyl, OC.sub.6-14-aryl, O-5 to 14 membered heteroaryl, SH, SC.sub.1-30-alkyl, SC.sub.2-30-alkenyl, SC.sub.2-30-alkynyl, SC.sub.5-8-cycloalkyl, SC.sub.5-8-cycloalkenyl, S-5 to 14 membered heterocycloalkyl, S-5 to 14 membered heterocycloalkenyl, SC.sub.6-14-aryl, S-5 to 14 membered heteroaryl, C(O)H, COC.sub.1-30-alkyl, COC.sub.2-30-alkenyl, COC.sub.2-30-alkynyl, COC.sub.5-8-cycloalkyl, COC.sub.5-8-cycloalkenyl, CO-5 to 14 membered heterocycloalkyl, CO-5 to 14 membered heterocycloalkenyl, COC.sub.6-14-aryl, CO-5 to 14 membered heteroaryl, COOH, NH(C.sub.1-30-alkyl), N(C.sub.1-30-alkyl).sub.2, CONH.sub.2, CONH(C.sub.1-30-alkyl), CON(C.sub.1-30-alkyl).sub.2, SO.sub.2OH, SO.sub.2NH.sub.2, SO.sub.2C.sub.1-30-alkyl and SO.sub.2C.sub.6-14-aryl, wherein C.sub.1-30-alkyl, C.sub.2-30-alkenyl and C.sub.2-30-alkynyl, are optionally substituted with one to nine substituents independently selected from the group consisting of C.sub.5-6-cycloalkyl, C.sub.5-6-cycloalkenyl, 5 to 10 membered heterocycloalkyl, 5 to 10 membered heterocycloalkenyl, C.sub.6-10-aryl, 5 to 10 membered heteroaryl, OR.sup.a, OC(O)R.sup.a, C(O)OR.sup.a, C(O)R.sup.a, NR.sup.aR.sup.b, NR.sup.a[C(O)R.sup.b], N[C(O)R.sup.a][C(O)R.sup.b], halogen, CN and NO.sub.2; and one or more CH.sub.2-groups, but not adjacent CH.sub.2-groups of C.sub.1-30-alkyl, C.sub.2-30-alkenyl and C.sub.2-30-alkynyl, and not the CH.sub.2-group directly attached to the core of the compound of formula (1), is optionally replaced by O or S, and C.sub.5-8-cycloalkyl, C.sub.5-8-cycloalkenyl, 5 to 14 membered heterocycloalkyl and 5 to 14 membered heterocycloalkenyl are optionally substituted with one to five substituents independently selected from the group consisting of C.sub.1-20-alkyl, C.sub.2-20-alkenyl, C.sub.2-20-alkynyl, C.sub.1-10-aryl, 5 to 10 membered heteroaryl, OR.sup.a, OC(O)R.sup.a, C(O)OR.sup.a, C(O)R.sup.a, NR.sup.aR.sup.b, NR.sup.a[C(O)R.sup.b], N[C(O)R.sup.a][C(O)R.sup.b], halogen, CN and NO.sub.2, C.sub.6-14-aryl is optionally substituted with one to five substituents independently selected from the group consisting of C.sub.1-20-alkyl, C.sub.2-20-alkenyl, C.sub.2-20-alkynyl, C.sub.5-6-cycloalkyl, C.sub.5-6-cycloalkenyl, 5 to 10 membered heterocycloalkyl, 5 to 10 membered heterocycloalkenyl, and 5 to 10 membered heteroaryl, OR.sup.a, OC(O)R.sup.a, C(O)OR.sup.a, C(O)R.sup.a, NR.sup.aR.sup.b, NR.sup.a[C(O)R.sup.b], N[C(O)R.sup.a][C(O)R.sup.b], halogen, CN and NO.sub.2, 5 to 14 membered heteroaryl is optionally substituted with one to five substituents independently selected from the group consisting of C.sub.1-20-alkyl, C.sub.2-20-alkenyl, C.sub.2-20-alkynyl, C.sub.5-6-cycloalkyl, C.sub.5-6-cycloalkenyl, 5 to 10 membered heterocycloalkyl, 5 to 10 membered heterocycloalkenyl, C.sub.6-10-aryl, OR.sup.a, OC(O)R.sup.a, C(O)OR.sup.a, C(O)R.sup.a, NR.sup.aR.sup.b, NR.sup.a[C(O)R.sup.b], N[C(O)R.sup.a][C(O)R.sup.b], halogen, CN and NO.sub.2, wherein R.sup.a and R.sup.b are independently selected from the group consisting of H, C.sub.1-20-alkyl, C.sub.2-20-alkenyl and C.sub.2-20-alkynyl, C.sub.1-20-alkyl, C.sub.2-20-alkenyl and C.sub.2-20-alkynyl are optionally substituted with one to five substituents independently selected from the group consisting of phenyl, OR.sup.c, OC(O)R.sup.c, C(O)OR.sup.c, C(O)R.sup.c, NR.sup.cR.sup.d, NR.sup.c[C(O)R.sup.d], N[C(O)R.sup.c][C(O)R.sup.d], halogen, CN and NO.sub.2, and, C.sub.5-6-cycloalkyl, C.sub.5-6-cycloalkenyl, 5 to 10 membered heterocycloalkyl, 5 to 10 membered heterocycloalkenyl, C.sub.6-10-aryl and 5 to 10 membered heteroaryl are optionally substituted with one to five substituents independently selected from the group consisting of C.sub.1-10-alkyl, C.sub.2-10-alkenyl, C.sub.2-10-alkynyl, OR.sup.c, OC(O)R.sup.c, C(O)OR.sup.c, C(O)R.sup.c, NR.sup.cR.sup.d, NR.sup.c[C(O)R.sup.d], N[C(O)R.sup.c][C(O)R.sup.d], halogen, CN and NO.sub.2, wherein R.sup.c and R.sup.d are independently selected from the group consisting of H, C.sub.1-10-alkyl, C.sub.2-10-alkenyl and C.sub.2-10-alkynyl, wherein C.sub.1-10-alkyl, C.sub.2-10-alkenyl and C.sub.2-10-alkynyl are optionally substituted with one to five substituents independently selected from the group consisting of halogen, CN and NO.sub.2.

12. The compound of claim 11, wherein R.sup.1 and R.sup.2 are independently from each other selected from the group consisting of H, C.sub.1-30-alkyl, C.sub.6-14-aryl, and 5 to 14 membered heteroaryl, and R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 are independently from each other selected from the group consisting of H, C.sub.1-30-alkyl, C.sub.6-14-aryl, 5 to 14 membered heteroaryl, halogen, CN, SCN, NO.sub.2, OH, OC.sub.1-30-alkyl, OC.sub.6-14-aryl, O-5 to 14 membered heteroaryl, SH, SC.sub.1-30-alkyl, SC.sub.6-14-aryl, S-5 to 14 membered heteroaryl, C(O)H, COC.sub.1-30-alkyl, COC.sub.6-14-aryl, CO-5 to 14 membered heteroaryl, COOH, NH(C.sub.1-30-alkyl), N(C.sub.1-30-alkyl).sub.2, CONH.sub.2, CONH(C.sub.1-30-alkyl), CON(C.sub.1-30-alkyl).sub.2, SO.sub.2OH, SO.sub.2NH.sub.2, SO.sub.2C.sub.1-30-alkyl and SO.sub.2C.sub.6-14-aryl, wherein C.sub.1-30-alkyl is optionally substituted with one to nine substituents independently selected from the group consisting of C.sub.6-10-aryl, 5 to 10 membered heteroaryl, OR.sup.a, OC(O)R.sup.a, C(O)OR.sup.a, C(O)R.sup.a, NR.sup.aR.sup.b, NR.sup.a[C(O)R.sup.b], N[C(O)R.sup.a][C(O)R.sup.b], halogen, CN and NO.sub.2; and one or more CH.sub.2-groups, but not adjacent CH.sub.2-groups of C.sub.1-30-alkyl and not the CH.sub.2-group directly attached to the core of the compound of formula (1), is optionally replaced by O or S, and C.sub.6-14-aryl is optionally substituted with one to five substituents independently selected from the group consisting of C.sub.1-20-alkyl, 5 to 10 membered heteroaryl OR.sup.a, OC(O)R.sup.a, C(O)OR.sup.a, C(O)R.sup.a, NR.sup.aR.sup.b, NR.sup.a[C(O)R.sup.b], N[C(O)R.sup.a][C(O)R.sup.b], halogen, CN and NO.sub.2, 5 to 14 membered heteroaryl is optionally substituted with one to five substituents independently selected from the group consisting of C.sub.1-20-alkyl, C.sub.6-10-aryl, OR.sup.a, OC(O)R.sup.a, C(O)OR.sup.a, C(O)R.sup.a, NR.sup.aR.sup.b, NR.sup.a[C(O)R.sup.b], N[C(O)R.sup.a][C(O)R.sup.b], halogen, CN and NO.sub.2, wherein R.sup.a and R.sup.b are independently selected from the group consisting of H and C.sub.1-20-alkyl, C.sub.1-20-alkyl is optionally substituted with one to five substituents selected from the group consisting of phenyl, OR.sup.c, OC(O)R.sup.c, C(O)OR.sup.c, C(O)R.sup.c, NR.sup.cR.sup.d, NR.sup.c[C(O)R.sup.d], N[C(O)R.sup.c][C(O)R.sup.d], halogen, CN and NO.sub.2, and, C.sub.6-10-aryl and 5 to 10 membered heteroaryl are optionally substituted with one to five substituents independently selected from the group consisting of C.sub.1-10-alkyl, OR.sup.c, OC(O)R.sup.c, C(O)OR.sup.c, C(O)R.sup.c, NR.sup.cR.sup.d, NR.sup.c[C(O)R.sup.d], N[C(O)R.sup.c][C(O)R.sup.d], halogen, CN and NO.sub.2, wherein R.sup.c and R.sup.d are independently selected from the group consisting of H and C.sub.1-10-alkyl, wherein C.sub.1-10-alkyl is optionally substituted with one to five substituents independently selected from the group consisting of halogen, CN and NO.sub.2.

13. The compound of claim 11, wherein R.sup.1 and R.sup.2 are independently from each other selected from the group consisting of C.sub.6-14-aryl, and 5 to 14 membered heteroaryl, and R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 are independently from each other selected from the group consisting of H and C.sub.1-30-alkyl, wherein C.sub.1-30-alkyl is optionally substituted with one to nine substituents independently selected from the group consisting of C.sub.6-10-aryl, 5 to 10 membered heteroaryl, OR.sup.a, OC(O)R.sup.a, C(O)OR.sup.a, C(O)R.sup.a, NR.sup.aR.sup.b, NR.sup.a[C(O)R.sup.b], N[C(O)R.sup.a][C(O)R.sup.b], halogen, CN and NO.sub.2; and one or more CH.sub.2-groups, but not adjacent CH.sub.2-groups of C.sub.1-30-alkyl and not the CH.sub.2-group directly attached to the core of the compound of formula (1), is optionally replaced by O or S, and C.sub.6-14-aryl is optionally substituted with one to five substituents independently selected from the group consisting of C.sub.1-20-alkyl, 5 to 10 membered heteroaryl, OR.sup.a, OC(O)R.sup.a, C(O)OR.sup.a, C(O)R.sup.a, NR.sup.aR.sup.b, NR.sup.a[C(O)R.sup.b], N[C(O)R.sup.a][C(O)R.sup.b], halogen, CN and NO.sub.2, 5 to 14 membered heteroaryl is optionally substituted with one to five substituents independently selected from the group consisting of C.sub.1-20-alkyl, C.sub.6-10-aryl, OR.sup.a, OC(O)R.sup.a, C(O)OR.sup.a, C(O)R.sup.a, NR.sup.aR.sup.b, NR.sup.a[C(O)R.sup.b], N[C(O)R.sup.a][C(O)R.sup.b], halogen, CN and NO.sub.2, wherein R.sup.a and R.sup.b are independently selected from the group consisting of H and C.sub.1-20-alkyl, C.sub.1-20-alkyl is optionally substituted with one to five substituents selected from the group consisting of phenyl, OR.sup.c, OC(O)R.sup.c, C(O)OR.sup.c, C(O)R.sup.c, NR.sup.cR.sup.d, NR.sup.c[C(O)R.sup.d], N[C(O)R.sup.c][C(O)R.sup.d], halogen, CN and NO.sub.2, and, C.sub.6-10-aryl and 5 to 10 membered heteroaryl are optionally substituted with one to five substituents independently selected from the group consisting of C.sub.1-10-alkyl, OR.sup.c, OC(O)R.sup.c, C(O)OR.sup.c, C(O)R.sup.c, NR.sup.cR.sup.d, NR.sup.c[C(O)R.sup.d], N[C(O)R.sup.c][C(O)R.sup.d], halogen, CN and NO.sub.2, wherein R.sup.c and R.sup.d are independently selected from the group consisting of H and C.sub.1-10-alkyl, wherein C.sub.1-10-alkyl is optionally substituted with one to five substituents independently selected from the group consisting of halogen, CN and NO.sub.2.

14. The compound of claim 11, wherein R.sup.1 and R.sup.2 are independently from each other selected from the group consisting of C.sub.6-14-aryl, and 5 to 14 membered heteroaryl, and R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 are independently from each other selected from the group consisting of H and C.sub.1-30-alkyl, wherein C.sub.1-30-alkyl is optionally substituted with one to nine substituents independently selected from halogen, and C.sub.6-14-aryl is optionally substituted with one to five substituents independently selected from C.sub.1-20-alkyl.

15. The compound of claim 11, wherein R.sup.1 and R.sup.2 are independently from each other selected from the group consisting of phenyl, ##STR00028## which are optionally substituted with one or two substituents independently selected from C.sub.1-20-alkyl, and R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 are independently from each other selected from the group consisting of H and CF.sub.3.

16. A process for the preparation of the compound of claim 11, which process comprises the steps of i) reducing a compound of formula 2 ##STR00029## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 are as defined in claim 11, to the compound of formula 2 ##STR00030## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 are as defined in claim 11, and ii) treating the compound of formula 2 with a suitable catalyst to obtain a compound of formula 1.

17. A compound of formula ##STR00031## wherein R.sup.1 and R.sup.2 are independently from each other selected from the group consisting of H, C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-8-cycloalkyl, C.sub.5-8-cycloalkenyl, 5 to 14 membered heterocycloalkyl, 5 to 14 membered heterocycloalkenyl, C.sub.6-14-aryl and 5 to 14 membered heteroaryl, and R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, R.sup.9 and R.sup.10 are independently from each other selected from the group consisting of H, C.sub.1-30-alkyl, C.sub.2-30-alkenyl, C.sub.2-30-alkynyl, C.sub.5-8-cycloalkyl, C.sub.5-8-cycloalkenyl, 5 to 14 membered heterocycloalkyl, 5 to 14 membered heterocycloalkenyl, C.sub.6-14-aryl, 5 to 14 membered heteroaryl, halogen, CN, SCN, NO.sub.2, OH, OC.sub.1-30-alkyl, OC.sub.2-30-alkenyl, OC.sub.2-30-alkynyl, OC.sub.5-8-cycloalkyl, OC.sub.5-8-cycloalkenyl, O-5 to 14 membered heterocycloalkyl, O-5 to 14 membered heterocycloalkenyl, OC.sub.6-14-aryl, O-5 to 14 membered heteroaryl, SH, SC.sub.1-30-alkyl, SC.sub.2-30-alkenyl, SC.sub.2-30-alkynyl, SC.sub.5-8-cycloalkyl, SC.sub.5-8-cycloalkenyl, S-5 to 14 membered heterocycloalkyl, S-5 to 14 membered heterocycloalkenyl, SC.sub.6-14-aryl, S-5 to 14 membered heteroaryl, C(O)H, COC.sub.1-30-alkyl, COC.sub.2-30-alkenyl, COC.sub.2-30-alkynyl, COC.sub.5-8-cycloalkyl, COC.sub.5-8-cycloalkenyl, CO-5 to 14 membered heterocycloalkyl, CO-5 to 14 membered heterocycloalkenyl, COC.sub.6-14-aryl, CO-5 to 14 membered heteroaryl, COOH, NH(C.sub.1-30-alkyl), N(C.sub.1-30-alkyl).sub.2, CONH.sub.2, CONH(C.sub.1-30-alkyl), CON(C.sub.1-30-alkyl).sub.2, SO.sub.2OH, SO.sub.2NH.sub.2, SO.sub.2C.sub.1-30-alkyl and SO.sub.2C.sub.6-14-aryl, wherein C.sub.1-30-alkyl, C.sub.2-30-alkenyl and C.sub.2-30-alkynyl, are optionally substituted with one to nine substituents independently selected from the group consisting of C.sub.5-6-cycloalkyl, C.sub.5-6-cycloalkenyl, 5 to 10 membered heterocycloalkyl, 5 to 10 membered heterocycloalkenyl, C.sub.6-10-aryl, 5 to 10 membered heteroaryl, OR.sup.a, OC(O)R.sup.a, C(O)OR.sup.a, C(O)R.sup.a, NR.sup.aR.sup.b, NR.sup.a[C(O)R.sup.b], N[C(O)R.sup.a][C(O)R.sup.b], halogen, CN and NO.sub.2; and one or more CH.sub.2-groups, but not adjacent CH.sub.2-groups of C.sub.1-30-alkyl, C.sub.2-30-alkenyl and C.sub.2-30-alkynyl, and not the CH.sub.2-group directly attached to the core of the compound of formula (1), is optionally replaced by O or S, and C.sub.5-8-cycloalkyl, C.sub.5-8-cycloalkenyl, 5 to 14 membered heterocycloalkyl and 5 to 14 membered heterocycloalkenyl are optionally substituted with one to five substituents independently selected from the group consisting of C.sub.1-20-alkyl, C.sub.2-20-alkenyl, C.sub.2-20-alkynyl, C.sub.6-10-aryl, 5 to 10 membered heteroaryl, OR, OC(O)R.sup.a, C(O)OR.sup.a, C(O)R.sup.a, NR.sup.aR.sup.b, NR.sup.a[C(O)R.sup.b], N[C(O)R.sup.a][C(O)R.sup.b], halogen, CN and NO.sub.2, C.sub.6-14-aryl is optionally substituted with one to five substituents independently selected from the group consisting of C.sub.1-20-alkyl, C.sub.2-20-alkenyl, C.sub.2-20-alkynyl, C.sub.5-6-cycloalkyl, C.sub.5-6-cycloalkenyl, 5 to 10 membered heterocycloalkyl, 5 to 10 membered heterocycloalkenyl, and 5 to 10 membered heteroaryl OR.sup.a, OC(O)R.sup.a, C(O)OR.sup.a, C(O)R.sup.a, NR.sup.aR.sup.b, NR.sup.a[C(O)R.sup.b], N[C(O)R.sup.a][C(O)R.sup.b], halogen, CN and NO.sub.2, 5 to 14 membered heteroaryl is optionally substituted with one to five substituents independently selected from the group consisting of C.sub.1-20-alkyl, C.sub.2-20-alkenyl, C.sub.2-20-alkynyl, C.sub.5-6-cycloalkyl, C.sub.5-6-cycloalkenyl, 5 to 10 membered heterocycloalkyl, 5 to 10 membered heterocycloalkenyl, C.sub.6-10-aryl, OR.sup.a, OC(O)R.sup.a, C(O)OR.sup.a, C(O)R.sup.a, NR.sup.aR.sup.b, NR.sup.a[C(O)R.sup.b], N[C(O)R.sup.a][C(O)R.sup.b], halogen, CN and NO.sub.2, wherein R.sup.a and R.sup.b are independently selected from the group consisting of H, C.sub.1-20-alkyl, C.sub.2-20-alkenyl and C.sub.2-20-alkynyl, C.sub.1-20-alkyl, C.sub.2-20-alkenyl and C.sub.2-20-alkynyl can be substituted with one to five substituents selected from the group consisting of phenyl, OR.sup.c, OC(O)R.sup.c, C(O)OR.sup.c, C(O)R.sup.c, NR.sup.cR.sup.d, NR.sup.c[C(O)R.sup.d], N[C(O)R.sup.c][C(O)R.sup.d], halogen, CN and NO.sub.2, and, C.sub.5-6-cycloalkyl, C.sub.5-6-cycloalkenyl, 5 to 10 membered heterocycloalkyl, 5 to 10 membered heterocycloalkenyl, C.sub.6-10-aryl and 5 to 10 membered heteroaryl are optionally substituted with one to five substituents independently selected from the group consisting of C.sub.1-10-alkyl, C.sub.2-10-alkenyl, C.sub.2-10-alkynyl, OR.sup.c, OC(O)R.sup.c, C(O)OR.sup.c, C(O)R.sup.c, NR.sup.cR.sup.d, NR.sup.c[C(O)R.sup.d], N[C(O)R.sup.c][C(O)R.sup.d], halogen, CN and NO.sub.2, wherein R.sup.c and R.sup.d are independently selected from the group consisting of H, C.sub.1-10-alkyl, C.sub.2-10-alkenyl and C.sub.2-10-alkynyl, wherein C.sub.1-10-alkyl, C.sub.2-10-alkenyl and C.sub.2-10-alkynyl are optionally substituted with one to five substituents selected from the group consisting of halogen, CN and NO.sub.2.

18. An electronic device comprising the compound of claim 11.

19. The electronic device of claim 18, wherein the electronic device is an organic field effect transistor (OFET).

20. A semiconducting material comprising the compound of claim 11.

Description

EXAMPLES

Example 1

Preparation of Compound 1a

[0131] ##STR00023##

Preparation of Compound 3a

[0132] Compound 3a was prepared as described by Potrawa, T.; Langhals, H. Chem. Ber. 1987, 120, 1075-1078.

Preparation of Compound 2a

[0133] A mixture of DPP 3a (400 mg, 1.39 mmol), 2-fluoro-5-trifluoromethyl-nitrobenzene (0.78 mL, 5.56 mmol) and K.sub.2CO.sub.3 (770 mg, 5.56 mmol) in DMF (200 mL) was stirred at 70 C. for 22 h, and the suspension became clear when the reaction is finished. Afterwards K.sub.2CO.sub.3 was removed by filtration and the solvent was removed by reduced pressure to get the crude product. Methanol (10 mL) was added to the crude product and the precipitate was filtered, washed with methanol (10 mL) until it became colorless, and dried under vacuum to get compound 2a as a yellow solid (490 mg, 53%).

[0134] .sup.1H NMR ([D.sub.6]DMSO, 400 MHz, 300 K): =8.60 (d, .sup.4J=1.8 Hz, 0.9H), 8.53 (d, .sup.4J=1.8 Hz, 1.1H), 8.25 (dd, .sup.4J=1.8 Hz, .sup.3J=8.7 Hz, 1.1H), 8.18 (dd, .sup.4J=1.6 Hz, .sup.3J=8.4 Hz, 0.9H), 7.86 (d, .sup.3J=8.1 Hz, 1.1H), 7.62-7.44 (m, 10.9H); the ratio of the isomers is 0.9/1.1. .sup.13C NMR ([D.sub.6]DMSO, 150 MHz, 343 K): =161.9, 159.4, 159.3, 146.5, 145.9, 145.7, 132.7, 132.0, 131.9, 131.8, 131.5, 131.4, 130.6, 130.54, 130.52, 129.8, 129.5, 128.9, 128.75, 128.67, 128.6, 125.7, 125.6, 125.0, 123.2, 122.8, 122.7, 122.54, 122.51, 121.4, 109.84, 109.79. MS (MALDI TOF, neg. mode, CHCl.sub.3): m/z: calculated for C.sub.32H.sub.16F.sub.6N.sub.4O.sub.6: 666.105 [M].sup., found: 666.039. HRMS (ESI, pos. mode, acetonitrile/chloroform 1:1): m/z: calculated for C.sub.32H.sub.17F.sub.6N.sub.4O.sub.6: 667.1052 [M+H].sup.+, found: 667.1050. CV (CH.sub.2Cl.sub.2, 0.1 M TBAHFP, vs. Fc/Fc.sup.+): E.sup.red (X/X.sup.)=1.43 V, E.sub.1/2.sup.ox (X/X.sup.+)=1.04 V. UV-Vis (CHCl.sub.3): .sub.max/nm ()=464 (23800 M.sup.1 cm.sup.1).

Preparation of Compound 1a

[0135] A mixture of compound 2a (120 mg, 0.18 mmol), and SnCl.sub.2.2H.sub.2O (410 mg, 1.8 mmol) in ethyl acetate (25 mL) was heated at 78 C. for 3 h under argon. After the solution was cooled down to room temperature, the pH is made slightly basic (pH 7-8) by addition of 10% aqueous sodium bicarbonate before extracting with ethyl acetate. The organic phase was collected and dried over magnesium sulfate, and the solvent was removed under reduced pressure to get the crude product, which was washed with methanol (5 mL) and dried under vacuum to get the desired intermediate product diamine-DPP, which was used for the next step without further purification. The crude diamine-DPP from previous step (110 mg) and DABCO (90 mg, 0.80 mmol) were dissolved in mesitylene (70 mL) while heating to 120 C. for 10 min. Titanium tetrachloride (0.14 mL, 1.30 mmol) in mesitylene (2 mL) was added dropwise to the reaction mixture and the solution was kept at 120 C. for additional 30 min. The hot reaction was dropped quickly in to 50 mL water, extracted with a small amount of ethyl acetate, and the organic phase was passed through a neutral aluminum oxide column using chloroform as eluent. The solvent was removed under vacuum and the residue was washed with 2 mL methanol to obtain the pure compound 1a as a red solid (15 mg). The total yield of the two steps from compound 2a to 1a is 15%.

[0136] .sup.1H NMR ([D.sub.2]tetrachloroethane, 600 Hz, 353 K): =8.15 (d, .sup.3J=7.4 Hz, 4H), 7.96 (s, 2H), 7.70-7.65 (m, 6H), 7.45 (d, 3J=8.5 Hz, 2H), 7.39 (d, 3J=8.5 Hz, 2H). .sup.13C NMR ([D.sub.2]tetrachloroethane, 150 Hz, 343 K): =139.3, 133.5, 132.4, 129.6, 129.5, 127.2, 126.0, 125.6, 124.0, 121.4, 121.3, 120.6, 119.1, 119.1, 120.0, 117.7, 116.9, 116.7, 116.5, 112.2. MS (MALDI TOF, neg. mode, CHCl.sub.3): m/z: calculated for C.sub.32H.sub.16F.sub.6N.sub.4: 570.128 [M].sup., found: 570.110. HRMS (ESI, pos. mode, acetonitrile/chloroform 1:1): m/z: calculated for C.sub.32H.sub.17F.sub.6N.sub.4: 571.1357 [M+H].sup.+, found: 571.1353. CV (CH.sub.2Cl.sub.2, 0.1 M TBAHFP, vs. Fc/Fc.sup.+): E.sub.1/2.sup.red (X/X.sup.)=1.31 V, E.sup.ox (X/X.sup.+)=0.99 V. UV-Vis (CHCl.sub.3): .sub.max/nm ()=484 (15700 M.sup.1 cm.sup.1).

Example 2

Preparation of Compound 1b

[0137] ##STR00024##

Preparation of Compound 3b

[0138] Compound 3b was prepared as described by Potrawa, T.; Langhals, H. Chem. Ber. 1987, 120, 1075-1078.

Preparation of Compound 2b

[0139] A mixture of DPP 3b (200 mg, 0.5 mmol), 2-fluoro-5-trifluoromethyl-nitrobenzene (0.28 mL, 2 mmol) and K.sub.2CO.sub.3 (276 mg, 2 mmol) in DM F (100 mL) was stirred at 70 C. for 24 h. After the reaction solution was cooled down to room temperature, K.sub.2CO.sub.3 was removed by filtration and the solvent was removed under reduced pressure to get the crude product. Methanol was added to the latter and the precipitate was filtered, washed with methanol until it became colorless and dried under vacuum to obtain compound 2b as a red solid (195 mg, 50%).

[0140] .sup.1H NMR: (CDCl.sub.3, 400 Hz, 300 K): =8.39 (d, .sup.4J=1.7 Hz, 0.8H), 8.34 (d, .sup.4J=1.8 Hz, 1.2H), 7.91 (dd, .sup.4J=1.6 Hz, .sup.3J=8.4 Hz, 1.2H), 7.79 (dd, .sup.4J=1.6 Hz, .sup.3J=8.4 Hz, 0.8H), 7.60-7.58 (m, 1.6H), 7.54-7.48 (m, 3.6H), 7.40-7.36 (m, 4H), 7.20 (d, .sup.3J=8.3 Hz, 0.8H), 1.30 (s, 7.2H), 1.29 (s, 10.8H). The ratio of the isomers is 0.8/1.2. .sup.13C NMR (CDCl.sub.3, 100 Hz, 300 K): =160.3, 160.1, 156.4, 156.3, 146.8, 146.7, 146.3, 145.9, 132.7, 132.6, 131.9, 131.5, 131.2, 131.1, 130.9, 130.3, 130.26, 130.23, 129.8, 129.5, 129.2, 126.14, 126.09 123.8, 123.4, 123.2, 122.99, 122.95 121.1, 110.8, 110.5, 31.0, 30.9. HRMS (ESI, pos. mode, acetonitrile/chloroform 1:1): m/z: calculated for C.sub.40H.sub.33F.sub.6N.sub.4O.sub.6: 779.2304 [M+H].sup.+, found: 779.2301. CV (CH.sub.2Cl.sub.2, 0.1 M TBAHFP, vs. Fc/Fc.sup.+): E.sup.red (X/X.sup.)=1.53 V, E.sub.1/2.sup.ox (X/X.sup.+)=0.94 V. UV-Vis (CHCl.sub.3): .sub.max/nm ()=483 (29600 M.sup.1 cm.sup.1).

Preparation of Compound 1b

[0141] A mixture of compound 2b (110 mg, 0.14 mmol), and SnCl.sub.2.2H.sub.2O (320 mg, 2.6 mmol) in ethyl acetate (25 mL) was heated at 78 C. for 3 h under argon. After the solution was cooled down to room temperature, the pH is made slightly basic (pH 7-8) by the addition of 10% aqueous sodium bicarbonate before extracting with ethyl acetate. The organic phase was separated and dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to get the crude product, which was washed with methanol and dried under vacuum to get the desired product diamine-DPP, which was used in the next step without further purification. The crude diamine-DPP from the previous step (100 mg) and DABCO (110 mg, 1.0 mmol) were dissolved in mesitylene (100 mL) while heating to 120 C. for 10 min. Titanium tetrachloride (0.18 mL, 1.65 mmol) in mesitylene (2 mL) was added dropwise to the reaction mixture, the solution was kept at 120 C. for about 50 min. After the reaction was finished, the hot solution was dropped immediately into 50 mL water, and extracted with a small amount of ethyl acetate. The organic phase was passed through a neutral aluminum oxide column using chloroform as eluent and the solvent was removed under reduced pressure. The residue was washed with methanol (2 mL) to get the compound 1b as a red solid (13 mg). The total yield of the two steps from 2b to 1b is 14%.

[0142] .sup.1H NMR (CDCl.sub.3, 400 Hz, 300 K): =8.12 (d, .sup.3J=8.3 Hz, 4H), 8.00 (s, 2H), 7.75 (d, .sup.3J=8.5 Hz, 2H), 7.56 (d, .sup.3J=8.5 Hz, 2H). 7.43 (d, .sup.3J=8.5 Hz, 2H), 1.26 (s, 18H). .sup.13C NMR (CDCl.sub.3, 100 Hz, 300 K): =155.1, 152.4, 148.3, 138.1, 135.4, 132.1, 128.0, 125.5, 125.0, 124.7, 124.6, 123.0, 122.0, 119.9, 117.6, 117.6, 115.7, 111.1, 30.2, 28.7. MS (MALDI TOF, neg. mode, CHCl.sub.3): m/z: calculated for C.sub.40H.sub.32F.sub.6N.sub.4: 682.253 [M].sup., found: 682.232. HRMS (ESI, pos. mode, acetonitrile/chloroform 1:1): m/z: calculated for C.sub.40H.sub.33F.sub.6N.sub.4: 683.2610 [M+H].sup.+, found: 683.2610. CV (CH.sub.2Cl.sub.2, 0.1 M TBAHFP, vs. Fc/Fc.sup.+): E.sub.1/2.sup.red (X/X.sup.)=1.39 V, E.sup.ox (X/X.sup.+)=0.96 V. UV-Vis (CHCl.sub.3): .sub.max/nm ()=494 (24900 M.sup.1 cm.sup.1).

Example 3

Preparation of Compound 1c

[0143] ##STR00025##

Preparation of Compound 3c

[0144] Compound 3c was prepared as described by Woo, C. H.; Beaujuge, P. M.; Holcombe, T. W.; Lee, O. P.; Frchet, J. M. J. J. Am. Chem. Soc. 2010, 132, 15547-15549.

Preparation of Compound 2c

[0145] A mixture of DPP 3c (400 mg, 1.33 mmol), 2-fluoro-5-trifluoromethyl-nitrobenzene (0.75 mL, 5.32 mmol) and K.sub.2CO.sub.3 (736 mg, 5.32 mmol) in DMF (50 mL) was stirred at 70 C. for 24 h. After the reaction was cooled down to room temperature, K.sub.2CO.sub.3 was removed by filtration, extracted twice with 5 mL chloroform, and the collected solvent was removed under reduced pressure. Methanol was added to the crude product and the precipitate was filtered, and washed with methanol until it became colorless, and dried under vacuum to get compound 2c as a red solid (489 mg, 54%).

[0146] .sup.1H NMR ([D.sub.6]DMSO, 600 Hz, 350 K): =8.69 (d, .sup.4J=2.0 Hz, 0.8H), 8.66 (d, .sup.4J=2.0 Hz, 1.2H), 8.38-8.36 (m, 4H), 8.25 (d, .sup.3J=8.2 Hz, 1.2H), 8.10 (d, .sup.3J=8.2 Hz, 0.8H), 7.95-7.93 (m, 2H), 7.29-7.27 (m, 2H); the ratio of the isomers is 0.8/1.2. .sup.13C NMR ([D.sub.6]DMSO, 150 Hz, 343 K): =161.9, 159.2, 159.1, 147.3, 147.2, 138.7, 38.6, 134.8, 134.7, 134.6, 134.30, 134.25, 134.1, 131.5, 131.3, 131.2, 131.12, 131.08, 128.4, 128.3, 128.2, 123.2, 123.0, 122.9, 122.8, 122.7, 121.4, 107.2. MS (MALDI TOF, neg. mode, CHCl.sub.3): m/z: calculated for C.sub.28H.sub.12F.sub.6N.sub.4O.sub.6S.sub.2: 678.010 [M].sup., found: 678.991. HRMS (ESI, pos. mode, acetonitrile/chloroform 1:1): m/z calculated for C.sub.28H.sub.13F.sub.6N.sub.4O.sub.6S.sub.2: 679.0181 [M+H].sup.+, found: 679.0174. CV (CH.sub.2Cl.sub.2, 0.1 M TBAHFP, vs. Fc/Fc.sup.+): E.sup.red (X/X.sup.)=1.37 V, E.sub.1/2.sup.ox (X/X.sup.+)=0.76 V, E.sub.1/2.sup.ox (X.sup.+/X.sup.2+)=1.09 V. UV-Vis (CHCl.sub.3): .sub.max/nm ()=502 (29100), 537 (33000 M.sup.1 cm.sup.1).

Preparation of Compound 1c

[0147] A mixture of compound 2c (130 mg, 0.20 mmol), and SnCl.sub.2.2H.sub.2O (344 mg, 2.6 mmol) in ethyl acetate (30 mL) was heated at 70 C. for 3 h under argon. After the solution was cooled down to room temperature, the pH was made slightly basic (pH 7-8) by the addition of 10% aqueous sodium bicarbonate before extracting with ethyl acetate. The organic phase was separated and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue was dried under vacuum to get the desired product diamine-DPP, which was used for the next step without further purification.

[0148] The crude product from the previous step (120 mg) and DABCO (140 mg, 1.25 mmol) were dissolved in mesitylene (150 mL) while heating to 125 C. for 10 min. Titanium tetrachloride (0.18 mL, 1.63 mmol) in mesitylene (2 mL) was added dropwise to the reaction mixture, the solution was kept at 125 C. for about 60 min. The hot reaction solution was dropped quickly into 50 mL water, extracted with a small amount of ethyl acetate, and the organic phase was passed through a neutral aluminum oxide column using chloroform as eluent. The solvent was removed under reduced pressure and the residue was washed with methanol to get pure 1c as a dark brown solid (22 mg). The total yield of the two steps from 2c to 1c is 20%.

[0149] .sup.1H NMR ([D.sub.2]tetrachloroethane, 600 Hz, 350 K): =8.50 (dd, .sup.3J=3.7 Hz, .sup.4J=0.8 Hz, 2H), 8.01-8.0 (m, 4H), 7.78 (dd, 3J=5.0 Hz, 4J=0.9 Hz, 2H), 7.46 (dd, 3J=8.5 Hz, 4J=1.0 Hz, 2H), 7.42-7.40 (m, 2H). .sup.13C NMR ([D.sub.2]tetrachloroethane, 150 Hz, 343 K): =153.3, 149.7, 134.8, 133.2, 132.3, 131.9, 129.6, 128.9, 126.4, 126.1, 125.6, 123.9, 123.8, 121.30, 121.28, 120.6, 119.12, 119.09, 116.7, 116.5, 116.2, 112.5, 99.9, 80.1, 80.0, 79.8. MS (MALDI TOF, neg. mode, CHCl.sub.3): m/z: calculated for C.sub.28H.sub.12F.sub.6N.sub.4S.sub.2: 582.041 [M].sup., found: 582.002. HRMS (ESI, pos. mode, acetonitrile/chloroform 1:1): m/z: calculated for C.sub.28H.sub.13F.sub.6N.sub.4S.sub.2: 583.0486. [M+H].sup.+, found: 583.0483. CV (CH.sub.2Cl.sub.2, 0.1 M TBAHFP, vs. Fc/Fc.sup.+): E.sub.1/2.sup.red (X/X.sup.)=1.27 V, E.sup.ox (X/X.sup.+)=0.84 V, E.sup.ox (X.sup.+/X.sup.2+)=1.02 V. UV-Vis (CHCl.sub.3): .sub.max/nm ()=527 (25500 M.sup.1 cm.sup.1).

Example 4

Preparation of Compound 1d

[0150] ##STR00026##

Preparation of Compound 3d

[0151] Compound 3d was prepared as described by Woo, C. H.; Beaujuge, P. M.; Holcombe, T. W.; Lee, O. P.; Frchet, J. M. J. J. Am. Chem. Soc. 2010, 132, 15547-15549.

Preparation of Compound 2d

[0152] A mixture of DPP 3d (400 mg, 1.5 mmol), 2-fluoro-5-trifluoromethyl-nitrobenzene (0.64 mL, 6.0 mmol) and K.sub.2CO.sub.3 (828 mg, 3.0 mmol) in DMF (160 mL) was stirred at 70 C. for 5 h. K.sub.2CO.sub.3 was removed by filtration and the solvent was removed under reduced pressure. Methanol was added to the crude product and the solid was filtered, washed with methanol until it became colorless and dried under vacuum, affording 2d as a red solid (550 mg, 57%).

[0153] .sup.1H NMR ([D.sub.6]DMSO, 600 Hz, 300 K): =8.66 (d, .sup.4J=2.0 Hz, 0.8H), 8.63 (d, .sup.4J=2.0 Hz, 1.2H), 8.39-8.36 (m, 2H), 8.22 (d, .sup.3J=8.2 Hz, 1.2H), 8.08 (d, .sup.3J=8.2 Hz, 0.8H), 7.89 (dd, .sup.3J=1.6 Hz, 4J=0.5 Hz, 0.8H), 7.87 (dd, 3J=1.6 Hz, 4J=0.5 Hz, 1.2H), 7.80-7.79 (m, 2H), 6.84-6.82 (m, 2H); the ratio of the isomers 0.8/1.2. .sup.13C NMR ([D.sub.6]DMSO, 150 Hz, 343 K): =158.9, 148.6, 148.4, 146.7, 146.6, 142.5, 142.3, 133.7, 133.4, 132.7, 132.6, 132.3, 131.2, 131.1, 130.6, 130.4, 123.7, 123.0, 122.8, 122.7, 121.9, 121.8, 120.6, 120.4, 114.1, 114.0, 105.8, 54.9. HRMS (ESI, pos. mode, acetonitrile/chloroform 1:1): m/z calculated for C.sub.28H.sub.13F.sub.6N.sub.4O.sub.8: 647.0638, [M+H].sup.+, found: 647.0603. CV (CH.sub.2Cl.sub.2, 0.1 M TBAHFP, vs. Fc/Fc.sup.+): E.sup.red (X/X.sup.)=1.39 V, E.sub.1/2.sup.ox (X/X.sup.+)=0.75 V, E.sub.1/2.sup.ox (X.sup.+/X.sup.2+)=0.94 V. UV-Vis (CHCl.sub.3): .sub.max/nm ()=492 (31400), 530 (46700 M.sup.1 cm.sup.1).

Preparation of Compound 1d

[0154] This compound was synthesized from compound 2d by using the same procedure as applied for the synthesis of compound 1c from 2c. Yield of 1d: 17%.

[0155] .sup.1H NMR ([D.sub.2]tetrachloroethane, 600 Hz, 350 K): =8.39 (d, .sup.3J=2.9 Hz, 2H), 8.28 (d, .sup.3J=8.4 Hz, 2H), 7.98 (s, 2H), 7.86 (2H), 7.52 (d, .sup.3J=8.4 Hz, 2H). 6.89-6.88 (m, 2H). MS (MALDI TOF, neg. mode, CHCl.sub.3): m/z: calculated for C.sub.28H.sub.12F.sub.6N.sub.4O.sub.2: 550.086 [M].sup., found: 550.013. HRMS (ESI, pos. mode, acetonitrile/chloroform 1:1): m/z: calculated for C.sub.28H.sub.13F.sub.6N.sub.4O.sub.2: 551.0943 [M+H].sup.+, found: 551.0936. CV (CH.sub.2Cl.sub.2, 0.1 M TBAHFP, vs. Fc/Fc.sup.+): E.sub.1/2.sup.red (X/X.sup.)=1.27 V, E.sup.ox (X/X.sup.+)=0.72 V, E.sup.ox (X.sup.+/X.sup.2+)=1.06 V. UV-Vis (CHCl.sub.3): .sub.max/nm ()=570 (28500 M.sup.1 cm.sup.1).

Example 5

Test of the Chemical Stability of Compound 1a

[0156] Compound 1a was dissolved in chloroform (c=9.010.sup.6 M), and stored under ambient air and light conditions at room temperature. UV-Vis absorption spectra of compound 1a, dissolved in chloroform (c=9.010.sup.6 M), were recorded after 0, 1, 2, 3 and 4 days of storage at room temperature in a conventional quartz cell (light pass 10 mm) on a Perkin-Elmer Lambda 950 spectrometer. No chemical modification, such as degradation, was observed after 4 days.

Example 6

Preparation of Transistors Comprising Compound 1c as Semiconducting Material

[0157] Highly doped p-type silicon (100) wafers (0.01-0.02 .Math.cm) were used as substrates A. Highly doped p-type silicon (100) wafers (0.005-0.02 .Math.cm) with a 100 nm thick thermally grown SiO.sub.2 layer (capacitance 34 nF/cm.sup.2) were used as substrates B.

[0158] Onto substrates A, a 30 nm thick layer of aluminum is deposited by thermal evaporation in a Leybold UNIVEX 300 vacuum evaporator from a tungsten wire, at a pressure of 210.sup.6 mbar and with an evaporation rate of 1 nm/s. The surface of the aluminum layer is oxidized by a brief exposure to an oxygen plasma in an Oxford reactive ion etcher (RIE, oxygen flow rate: 30 sccm, pressure: 10 mTorr, plasma power: 200 W, plasma duration 30 sec) and the substrate is then immersed into a 2-propanol solution of a phosphonic acid (1 mMol solution of C.sub.14H.sub.29PO(OH).sub.2 [TDPA] or 1 mMol solution of C.sub.7F.sub.15C.sub.11H.sub.22PO(OH).sub.2 [FODPA]) and left in the solution for 1 hour, which results in the formation of a self-assembled monolayer (SAM) of phosphonic acid molecules on the aluminum oxide surface. The substrate is taken out of the solution and rinsed with pure 2-propanol, dried in a stream of nitrogen and left for 10 min on a hotplate at a temperature of 100 C. The total capacitance of the AlO.sub.x/SAM gate dielectric on substrate A is 810 nF/cm.sup.2 in case of C.sub.14H.sub.29PO(OH).sub.2 and 710 nF/cm.sup.2 in case of C.sub.7F.sub.15C.sub.11H.sub.22PO(OH).sub.2.

[0159] On substrates B, an about 8 nm thick layer of Al.sub.2O.sub.3 is deposited by atomic layer deposition in a Cambridge NanoTech Savannah (80 cycles at a substrate temperature of 250 C.). The surface of the aluminum oxide layer is activated by a brief exposure to an oxygen plasma in an Oxford reactive ion etcher (RIE, oxygen flow rate: 30 sccm, pressure: 10 mTorr, plasma power: 200 W, plasma duration 30 sec) and the substrate is then immersed into a 2-propanol solution of a phosphonic acid (1 mMol solution of C.sub.14H.sub.29PO(OH).sub.2 [TDPA] or 1 mMol solution of C.sub.7F.sub.15C.sub.11H.sub.22PO(OH).sub.2 [FODPA]) and left in the solution for 1 hour, which results in the formation of a self-assembled monolayer (SAM) of phosphonic acid molecules on the aluminum oxide surface. The substrate is taken out of the solution and rinsed with pure 2-propanol, dried in a stream of nitrogen and left for 10 min on a hotplate at a temperature of 100 C. The total capacitance of the SiO.sub.2/AlO.sub.x/SAM gate dielectric on substrate B is 32 nF/cm.sup.2 (independent on the choice of the phosphonic acid).

[0160] The contact angle of water on the TDPA-treated substrates is 108, and on the FODPA-treated substrates 118.

[0161] A 30 nm thick film of the compound 1c is deposited by thermal sublimation in a Leybold UNIVEX 300 vacuum evaporator from a molybdenum boat, at a pressure of 210.sup.6 mbar and with an evaporation rate of 0.3 nm/s.

[0162] For the source and drain contacts 30 nm of gold is evaporated through a shadow mask in a Leybold UNIVEX 300 vacuum evaporator from tungsten boat, at a pressure of 210.sup.6 mbar and with an evaporation rate of 0.3 nm/s. The transistors have a channel length (L) ranging from 10 to 100 m and a channel width (W) ranging from 50 to 1000 m.

[0163] To be able to contact the back side of the silicon wafer, the wafer (which also serves as the gate electrode of the transistors) is scratched on the back side and coated with silver ink.

Example 7

Measuring the Electrical Characteristics of the Transistors of Example 6

[0164] The electrical characteristics of the transistors of example 6 are measured on a Micromanipulator 6200 probe station using an Agilent 4156C semiconductor parameter analyzer. All measurements are performed in air at room temperature. The probe needles are brought into contact with the source and drain contacts of the transistors by putting them down carefully on top of the gold contacts. The gate electrode is contacted through the metal substrate holder onto which the wafer is placed during the measurements.

[0165] To obtain the transfer curve the drain-source voltage (V.sub.DS) is held to 3 V (in case of substrate A) or 40 V (in case of substrate B). The gate-source voltage V.sub.GS is swept at medium speed from 0 to 3 V in steps of 0.03 V (substrate A) or from 0 to 40 V in steps of 0.4 V (substrate B) and back. The charge-carrier mobility is extracted in the saturation regime from the slope of (I.sub.D).sup.1/2 versus V.sub.GS.

[0166] To obtain the output characteristics the drain-source voltage (V.sub.DS) is swept at medium speed from 0 to 3 V in steps of 0.03 V (substrate A) and from 0 to 40 V in steps of 0.4 V (substrate B), while the gate-source voltage V.sub.GS is held at up to 8 different voltages (e.g. 0, 0.5, 1, 1.5, 2, 2.5, 3 V in case of substrate A or 0, 10, 20, 30, 40 V in case of substrate B).

[0167] The results are depicted in Table 1.

TABLE-US-00001 TABLE 1 Electron Substrate Hole Mobility On/Off Organic Temperature Mobility .sub.e Ratio Semiconductor Substrate SAM T.sub.sub [ C.] .sub.p [cm.sup.2/Vs] [cm.sup.2/Vs] I.sub.on/I.sub.off 1c B FODPA 50 10.sup.3 10.sup.2 1c B TDPA 50 10.sup.5 10 1c A FODPA 50 10.sup.3 10.sup.2