Method of preparation of a precursor oligocene
AssigneeKoninklijke Philips Electronics N.V.
InventorsWolter Ten Hoeve, Bart-Hendrik Huisman
Life of this patent
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Abstract
The synthesis of a precursor oligocene, particularly pentacene, is a two-step process. In the first step the Diels-Alder adduct of the a,b-dihydro-a,b-etheno-oligocene with a 1,1-dialkoxy-cyclopentadiene is formed. In the second step this Diels-Alder adduct is converted into the precursor oligocene, in that first the corresponding keto-compound is formed, which may be eliminated thereafter. The resulting precursor oligocene can be converted to the oligocene with a heat treatment, particularly after providing a solution hereof on a substrate. It is suitable for use as semiconductor material in a thin-film transistor. Formula (I).
Claims9
A method of preparation of a precursor oligocene compound comprising a cyclohexadienyl-group, the precursor oligocene having the formula
- in which:
- the cyclohexadienyl-group is optionally provided with a —C(O)-bridge between its 2 and 5 positions;
- R3, R4 are the same as R1, R2 or are H, alkyl, aryl, alkoxy, aryloxy or halogen
- R5, R6 are H, C1-C4-alkyl, CN, C1-C4-alkoxy or halogen and may be the same or different;
- R7, R8, R9, R10 are H, alkyl, aryl, halogen or alkoxy, and may be the same or different, and R7 and R8, R8 and R9, R9 and R10 may be in combination
- A1, A2, A3, A4, are H or an electron withdrawing group selected from the group consisting of Cl, Br, I, F, H, CN, OCH3, CF3, and may be the same or different,
- wherein the method comprises the acts of:
- a) reacting a dihydro-etheno-oligocene of the formula
- with a 1,1-disubstituted-cyolopentadiene of the formula
- to form a Diels-Alder adduct of the formula
- in which
- R1-R6 and A1-A4 are the same as above, and
- R11, R12 is H, C1-C8-alkyl, aryl, aralkyl or alkaryl and R1 and R2 may be different or equal to each other, and may form together a ringshaped chain;
- and
- b) converting the adduct with an electrophilic or oxidizing agent to obtain the precursor oligocene compound.
A precursor oligocene compound of the formula
- in which
- R3, R4 are the same as R1, R2 or are H, alkyl, aryl, alkoxy, aryloxy, or halogen;
- R5, R6 are H, C1-C4-alkyl, CN, C1- C4-alkoxy or halogen, and may be the same or different;
- R7, R8, R9, R10 are H, alkyl, aryl, halogen or alkoxy, and may be the same or different, and R7 and R8, R8 and R9, R9and R10 may be in combination
- A1, A2, A3, A4, are H or an electron withdrawing group selected from the consisting of Cl, Br, I, F, H, CN, OCH3, CF3, and may be the same or different.
An intermediate of the formula
- in which
- R3, R4 are the same as R1, R2 or are H, alkyl, aryl, alkoxy, aryloxy, or halogen;
- R5, R6 are H, C1-C4-alkyl, CN, C1-C4-alkoxy or halogen and may be the same or different;
- R7, R8 , R9R10are H, alkyl, aryl, halogen or alkoxy, and may be the same or different, and R7 and R8,R8and R9, R9and R10may be in combination
- A1, A2, A3, A4, are H or an electron withdrawing group selected from the group consisting of Cl, Br, I, F, H, CN, OCH3, CF3, and may be the same or different;
- and
- R11 , R12 are H, C1 -C8-alkyl, aryl, aralkyl, or alkaryl, and R1 and R2 may be different or equal to each other, and may form together a ringshaped chain.
Dependencies are inferred from the claim text.