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US 7,723,521 B2Granted
Azaperylenes as organic semiconductors
AssigneeCiba Specialty Chemicals Corporation
InventorsFrank Bienewald, Beat Schmidhalter, Ulrich Berens, Hans Jürg Kirner
Life of this patent
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Abstract
A novel semiconductor device comprises an azaperylene organic semiconductor of the formula I wherein the substitutents are defined herein.
Claims19
A semiconductor device, or a device containing a semiconductor element, which semiconductor device or device containing a semiconductor element comprises an azaperylene organic semiconductor of the formula I
- wherein
- each of R1, R2, R3 and R4 independently is selected from H, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted aryl, halogen, substituted silyl, XR6;
- or one or more of R1 and R2, R2 and R3, R3 and R4, together with the carbon atoms they are bonding to, form a saturated or unsaturated, unsubstituted or substituted carbocyclic or heterocyclic ring;
- R5 is OR7, SR7, NR7R8, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, or unsubstituted or substituted aryl;
- R6 is substituted silyl, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted aryl;
- R7 is H, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted aryl;
- X is O, S, NR8;
- R8 is H, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted aryl and
- substituents, where present, bond to a carbon atom and are selected from the group consisting of C1-C22alkoxy, C1-C22alkyl, C4-C12cycloalkoxy, C4-C12cycloalkyl, OH, halogen, phenyl, and naphthyl;
- while saturated carbons also may be substituted by oxo (═O);
- 2 adjacent substituents may be linked together by abstraction of a hydrogen atom on each.
8 more elements
A compound of the formula I′
- wherein
- each of R1, R2, R3 and R4 independently is selected from H, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted aryl, halogen, Si(R11)3, XR6;
- or one or more of R1 and R2, R2 and R3, R3 and R4, together with the carbon atoms they are bonding to, form a saturated or unsaturated, unsubstituted or substituted carbocyclic or heterocyclic ring;
- R5 is H, OR7, SR7, NR7R8, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, or unsubstituted or substituted aryl;
- R6 is Si(R11)3, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted aryl;
- R7 is H, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted aryl;
- X is O, S, NR8;
- R8 is H, unsubstituted or substituted alkyl, unsubstituted or substituted alkenyl, unsubstituted or substituted alkynyl, unsubstituted or substituted aryl,
- R11 being C1-C20-alkyl or alkoxy,
- provided that at least one of R1, R2, R3, R4, R6, R7 is C4-C22alkyl, C10-C22phenylalkyl, or such residues interrupted by O, S, NR10, COO, OCNR10, OCOO, OCONR10, or NR10CNR10,
- R10 is hydrogen, C1-C12alkyl, or C4-C12cycloalkyl,
- and
- substituents, where present, bond to a carbon atom and are selected from the group consisting of C1-C22alkoxy, C1-C22alkyl, C4-C12cycloalkoxy, C4-C12cycloalkyl, OH, halogen, phenyl, and naphthyl;
- while saturated carbons also may be substituted by oxo (═O);
- 2 adjacent substituents may be linked together by abstraction of a hydrogen atom on each.
12 more elements
Dependencies are inferred from the claim text.