Organic semiconducting layers
AssigneeMerck Patent GmbH
InventorsBeverley Anne Brown, Janos Veres, Remi Manouk Anemian, Richard Williams, Simon Dominic Ogier, Stephen William Leeming
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Abstract
An organic semiconducting layer formulation containing an organic binder which has a permittivity, ∈, at 1,000 Hz of 3.3 or less and a polyacene compound of Formula A: and processes for the preparation thereof and uses thereof in various electronic devices.
Claims39
An organic semiconducting layer formulation, comprising an organic binder which has a permittivity, ∈, at 1,000 Hz of 3.3 or less;
- and a polyacene compound of Formula 1 or 8 or an isomer thereof
- wherein,
- R6 and R13 in the compound of Formula 1 are each independently the same or different and each independently represents:
- an optionally substituted C1-C40 carbyl or hydrocarbyl group;
- an optionally substituted C1-C40 alkoxy group;
- an optionally substituted C6-C40 aryloxy group;
- an optionally substituted C7-C40 alkylaryloxy group;
- an optionally substituted C2-C40 alkoxycarbonyl group;
- an optionally substituted C7-C40 aryloxycarbonyl group;
- a cyano group (—CN);
- a carbamoyl group (—C(═O)NH2);
- a haloformyl group (—C(═O)—X, wherein X represents a halogen atom);
- a formyl group (—C(═O)—H);
- an isocyano group;
- an isocyanate group;
- a thiocyanate group or a thioisocyanate group;
- an optionally substituted amino group;
- a hydroxy group;
- a nitro group;
- a CF3 group;
- a halogen group;
- or an optionally substituted silyl group;
- and
- R1, R2, R3, R4, R8, R9, R10, R11, R15, R16, and R17 in the compound of Formula 8 are each independently the same or different and each independently represents:
- H;
- an optionally substituted C1-C40 carbyl or hydrocarbyl group;
- an optionally substituted C1-C40 alkoxy group;
- an optionally substituted C6-C40 aryloxy group;
- an optionally substituted C7-C40 alkylaryloxy group;
- an optionally substituted C2-C40 alkoxycarbonyl group;
- an optionally substituted C7-C40 aryloxycarbonyl group;
- a cyano group (—CN);
- a carbamoyl group (—C(═O)NH2);
- a haloformyl group (—C(═O)—X, wherein X represents a halogen atom);
- a formyl group (—C(═O)—H);
- an isocyano group;
- an isocyanate group;
- a thiocyanate group or a thioisocyanate group;
- an optionally substituted amino group;
- a hydroxy group;
- a nitro group;
- a CF3 group;
- a halogen group;
- or an optionally substituted silyl group;
- and wherein independently each pair of R1 and R2, R2 and R3, R3 and R4, R8 and R9, R9 and R10, R10 and R11, R15 and R16 and R16 and R17 may be cross-bridged with each other to form a C4-C40 saturated or unsaturated ring, which saturated or unsaturated ring may be intervened by an oxygen atom, a sulphur atom or a group shown by formula:
- —N(Ra)— (wherein Ra is a hydrogen atom or a hydrocarbon group), or may optionally be substituted;
- and
- A represents Silicon or Germanium.
An OFET device, comprising an organic semiconducting layer formulation, wherein the organic semiconducting layer formulation comprises:
- a compound of Formula 1;
- a binder;
- and
- solvent,
- wherein the binder is poly(α-methylstyrene), linear olefin and cycloolefin(norbornene)copolymer, poly(4-methylstyrene), polystyrene or polystyrene-co-α-methylstyrene;
- and the solvent is toluene, ethylcyclohexane, anisole or pxylene.
An OFET device, comprising an organic semiconducting layer formulation, wherein the organic semiconducting layer formulation comprises:
- a compound of Formula 2;
- a binder;
- and
- solvent,
- wherein the binder is poly(α-methylstyrene), polyvinylcinnamate, or poly(4-vinylbiphenyl);
- and the solvent is 1,2-dichlorobenzene.
An OFET device, comprising an organic semiconducting layer formulation, wherein the organic semiconducting layer comprises:
- a compound of Formula 3;
- a binder;
- and
- a solvent,
- wherein:
- n and m are each independently 0, 1, 2, 3 or 4;
- the binder is poly(α-methylstyrene);
- and the solvent is toluene.
A compound of Formula 3
- wherein n and m are each independently 1 or 3.
An organic semiconducting layer formulation, comprising an organic binder which has a permittivity, ∈, at 1,000 Hz of 3.3 or less;
- and a polyacene compound which is
- a) 6,13-bis(triisopropylsilylethynyl)pentacene of Formula 1,
- or
- b) 2,3,9,10-tetramethyl,6,13-bis(triisopropylsilylethynyl)pentacene of Formula 2:
- or
- c) of Formula 3:
- wherein n and m are each independently 0, 1, 2, 3 or 4.
Dependencies are inferred from the claim text.