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US 6,211,369 B1Granted
Spiro compounds and the use thereof
AssigneeAventis Research & Technologies GmbH & Co. KG
InventorsJosef Salbeck, Donald Lupo
Life of this patent
Estimating the term…
Abstract
Spiro compounds of the formula (I), where X1, X2, X3, X4 are identical or different and are —S—, —O—, —NR5—, —CR5═N— or —CR5═CH—, with the proviso that at least one of the groups X1-4 is different from —CR5═CH—, are suitable as charge transport materials, in particular for photovoltaic cells, and as electroluminescence materials.
Claims5
A spiro compound of the formula (I),
- where the symbols have the following meanings:
- X1, X2, X3, X4 are identical or different and are —S—, —O—, —NR5—, —CR5═N—, —CR5═CH—,
- with the proviso that at least one of the groups X1-4 is different from —CR5═CH—;
- K1, L, M, N1, R1, R2, R3, R4 are identical or different and are each
- a) hydrogen, —NO2, —CN, —F or —Cl,
- b) a straight-chain or branched alkyl radical having from 1 to 20 carbon atoms, where
- b1) one or more nonadjacent CH2 groups can be replaced by —O—, —S—, —CO—O—, —O—CO—, —O—CO—O—, NR5 or —Si(CH3)2— and/or
- b2) one or more CH2 groups can be replaced by —CH═CH—, —C≡C—, 1,4-phenylene, 1,4-cyclohexylene or 1,3-cyclopentylene and/or
- b3) one or more H atoms can be replaced by F and/or Cl and/or
- c) one of the following groups:
- X, Y1 are in each case identical or different and are ═CR7— or ═N—;
- Z is —O—, —S—, —NR5—, —CRR—, —CR═CR— or —CR═N—;
- R5, R6 are in each case identical or different and are each
- a) hydrogen
- b) a straight-chain or branched alkyl radical having from 1 to 20 carbon atoms, where
- b1) one or more nonadjacent CH2 groups which are not bound to nitrogen can be replaced by —O—, —S—, —CO—O—, —O—CO—, —O—CO—O— or —Si(CH3)2 and/or
- b2) one or more CH2 groups can be replaced by —CH═CH—, —C≡C—, cyclopropane-1,2-diyl, 1,4-phenylene, 1,4-cyclohexylene or 1,3-cyclopentylene and/or
- b3) one or more H atoms can be replaced by F and/or Cl and/or
- b4) R5 and R6 together can also form a ring;
- c) phenyl, biphenyl, 1-naphthyl, 2-naphthyl, 2-thienyl, 2-furanyl;
- R7, R8, R9, R10, R11, R12 are identical or different and are each
- a) hydrogen, —CN, —F, NO2 or —Cl
- b) a straight-chain or branched alkyl radical having from 1 to 20 carbon atoms, where
- b1) one or more nonadjacent CH2 groups can be replaced by —O—, —S—, —CO—O—, —O—CO—, —O—CO—O—, —NR5 or —Si(CH3)2— and/or
- b2) one or more CH2 groups can be replaced by —CH═CH—, —C≡C—, cyclopropane-1,2-diyl, 1,4-phenylene, 1,4-cyclohexylene or 1,3-cyclopentylene and/or
- b3) one or more H atoms can be replaced by F and/or Cl;
- c) phenyl, biphenyl, 1-naphthyl, 2-naphthyl, 2-thienyl, 2-furanyl, —O-phenyl, —O-biphenyl, —O-1-naphthyl, —O-2-naphthyl, —O-2-thienyl, —O-2-furanyl,
- m, n, p, q, r are in each case identical or different and are 0, 1, 2, 3, 4, 5 or 6,
- with the exception of the compounds of the formula
- and also of 4,5-diazospirobifluorene and 4,4′,5,5′-tetraazospirobifluorene.
27 more elements
A charge transport material which comprises one or more spiro compounds of the formula
- where the symbols have the following meanings:
- X1, X2, X3, X4 are identical or different and are —S—, —O—, —NR5—, —CR5═N—, —CR5═CH—,
- with the proviso that at least one of the groups X1-4 is different from —CR5═CH—;
- K1, L, M, N1, R1, R2, R3, R4 are identical or different and are each
- a) hydrogen, —NO2, —CN, —F or —Cl,
- b) a straight-chain or branched alkyl radical having from 1 to 20 carbon atoms, where
- b1) one or more nonadjacent CH2 groups can be replaced by —O—, —S—, —CO—O—, —O—CO—, —O—CO—O—, NR5 or —Si(CH3)2— and/or
- b2) one or more CH2 groups can be replaced by —CH═CH—, —C≡C—, 1,4-phenylene, 1,4-cyclohexylene or 1,3-cyclopentylene and/or
- b3) one or more H atoms can be replaced by F and/or Cl and/or
- c) one of the following groups:
- X, Y1 are in each case identical or different and are ═CR7— or ═N—;
- Z is —O—, —S—, —NR5—, —CRR—, —CR═CR— or —CR═N—;
- R5, R6 are in each case identical or different and are each
- a) hydrogen
- b) a straight-chain or branched alkyl radical having from 1 to 20 carbon atoms, where
- b1) one or more nonadjacent CH2 groups which are not bound to nitrogen can be replaced by —O—, —S—, —CO—O—, —O—CO—;
- —O—CO—O— or —Si(CH3)2 and/or
- b2) one or more CH2 groups can be replaced by —CH═CH—, —C≡C—, cyclopropane-1,2-diyl, 1,4-phenylene, 1,4-cyclohexylene or 1,3-cyclopentylene and/or
- b3) one or more H atoms can be replaced by F and/or Cl and/or
- b4) R5 and R6 together can also form a ring;
- c) phenyl, biphenyl, 1-naphthyl, 2-naphthyl, 2-thienyl, 2-furanyl;
- R7, R8, R9, R10, R11, R12 are identical or different and are each
- a) hydrogen, —CN, —F, NO2 or —Cl
- b) a straight-chain or branched alkyl radical having from 1 to 20 carbon atoms, where
- b1) one or more nonadjacent CH2 groups can be replaced by —O—, —S—, —CO—O—, —O—CO—, —O—CO—O—, —NR5 or —Si(CH3)2— and/or
- b2) one or more CH2 groups can be replaced by —CH═CH—, —C≡C—, cyclopropane-1,2-diyl, 1,4-phenylene, 1,4-cyclohexylene or 1,3-cyclopentylene and/or
- b3) one or more H atoms can be replaced by F and/or Cl;
- c) phenyl, biphenyl, 1-naphthyl, 2-naphthyl, 2-thienyl, 2-furanyl, —O-phenyl, —O-biphenyl, —O-1-naphthyl, —O-2-naphthyl, —O-2-thienyl, —O-2-furanyl,
- m, n, p, q, r are in each case identical or different and are 0, 1, 2, 3, 4, 5 or 6.
26 more elements
Dependencies are inferred from the claim text.