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US 10,707,420 B2Granted
Polycyclic aromatic hydrocarbon copolymer-containing organic semiconductor compositions
AssigneeSmartkem Limited
InventorRussell Jon Griffiths
Life of this patent
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Abstract
The present invention relates to organic copolymers and organic semiconducting compositions comprising these materials, including layers and devices comprising such organic semiconductor compositions. The invention is also concerned with methods of preparing such organic semiconductor compositions and layers and uses thereof. The invention has application in the field of printed electronics and is particularly useful as a semiconducting material for use in formulations for organic thin film transistor (OTFT) backplanes for displays, integrated circuits, organic light emitting diodes (OLEDs), photodetectors, organic photovoltaic (OPV) cells, sensors, memory elements and logic circuits.
Claims27
An organic semiconductor composition comprising a Polycyclic Aromatic Hydrocarbon Copolymer (PAHC), wherein the PAHC is a random copolymer comprising at least one BXBX monomer unit having the Formula (A) and at least one monomer unit having the Formula (B):
- wherein
- Y1 and Y2 are independently S or Se;
- k and l are independently 0 or 1
- wherein each of R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11 and R12, which may be the same or different, independently represents hydrogen;
- a branched or unbranched, substituted or unsubstituted C1-C40 alkyl group;
- a branched or unbranched, substituted or unsubstituted C2-C40 alkenyl group;
- a branched or unbranched, substituted or unsubstituted C2-C40 alkynyl group;
- an optionally substituted C3-C40 cycloalkyl group;
- an optionally substituted C6-C40 aryl group;
- an optionally substituted C1-C40 heterocyclic group;
- an optionally substituted C1-C40 heteroaryl 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)NR15R16);
- a carbonyl group (—C(═O)—R17);
- a carboxyl group (—CO2R18) a cyanate group (—OCN);
- an isocyano group (—NC);
- an isocyanate group (—NCO);
- a thiocyanate group (—SCN) or a thioisocyanate group (—NCS);
- an optionally substituted amino group;
- a hydroxy group;
- a nitro group;
- a CF3 group;
- a halo group (Cl, Br, F, I);
- —SR19;
- —SO3H;
- —SO2R20;
- —SF5;
- an optionally substituted silyl group;
- a C2-C10 alkynyl group substituted with a SiH2R22 group, a C2-C10 alkynyl substituted with a SiHR22R23 group, or a C2-C10 alkynyl substituted with a —Si(R22)x(R23)x(R24)z group;
- wherein each R22 group is independently selected from the group consisting of a branched or unbranched, substituted or unsubstituted C1-C10 alkyl group, a branched or unbranched, substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted C2-C20 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, and a substituted or unsubstituted C6-C20 cycloalkylalkylene group;
- each R23 group is independently selected from the group consisting of a branched or unbranched, substituted or unsubstituted C1-C10 alkyl group, a branched or unbranched, substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C20 cycloalkyl group, and a substituted or unsubstituted C6-C20 cycloalkylalkylene group;
- R24 is independently selected from the group consisting of hydrogen, a branched or unbranched, substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted C2-C20 cycloalkyl group, a substituted or unsubstituted C6-C20 cycloalkylalkylene group, a substituted C5-C20 aryl group, a substituted or unsubstituted C6-C20 arylalkylene group, an acetyl group, a substituted or unsubstituted C3-C20 heterocyclic ring comprising at least one of O, N, S and Se in the ring;
- wherein x=1 or 2;
- y=1 or 2;
- z=0 or 1;
- and (x+y+z)=3;
- wherein each of R15, R16, R18, R19 and R20 independently represent H or optionally substituted C1-C40 carbyl or hydrocarbyl group optionally comprising one or more heteroatoms;
- wherein R17 represents a halogen atom, H or optionally substituted C1-C40 carbyl or C1-C40 hydrocarbyl group optionally comprising one or more heteroatoms;
- wherein k and 1 are independently 0 or 1;
- wherein at least two of R1, R3, R4, R6, R7, R9, R10, and R12, are a bond, represented by *, to another monomer unit having the Formula (A) or (B);
- and
- wherein Ar1, Ar2 and Ar3, which may be the same or different, each represent, independently if in different repeat units, an optionally substituted C6-40 aromatic group (mononuclear or polynuclear);
- and
- a polyacene small molecule, wherein the PAHC has a permittivity at 1000 Hz of between 3.4 and 8.0 or between 3.4 and 4.5.
46 more elements
An organic semiconductor composition comprising a Polycyclic Aromatic Hydrocarbon Copolymer (PAHC), wherein the PAHC is a random copolymer comprising at least one BXBX monomer unit having the Formula (A) and at least one monomer unit having the Formula (B):
- wherein
- Y1 and Y2 are independently S or Se;
- k and l are independently 0 or 1
- wherein each of R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11 and R12, which may be the same or different, independently represents hydrogen;
- a branched or unbranched, substituted or unsubstituted C1-C40 alkyl group;
- a branched or unbranched, substituted or unsubstituted C2-C40 alkenyl group;
- a branched or unbranched, substituted or unsubstituted C2-C40 alkynyl group;
- an optionally substituted C3-C40 cycloalkyl group;
- an optionally substituted C6-C40 aryl group;
- an optionally substituted C1-C40 heterocyclic group;
- an optionally substituted C1-C40 heteroaryl 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)NR15R16);
- a carbonyl group (—C(═O)—R17);
- a carboxyl group (—CO2R18) a cyanate group (—OCN);
- an isocyano group (—NC);
- an isocyanate group (—NCO);
- a thiocyanate group (—SCN) or a thioisocyanate group (—NCS);
- an optionally substituted amino group;
- a hydroxy group;
- a nitro group;
- a CF3 group;
- a halo group (Cl, Br, F, I);
- —SR19;
- —SO3H;
- —SO2R20;
- —SF5;
- an optionally substituted silyl group;
- a C2-C10 alkynyl group substituted with a SiH2R22 group, a C2-C10 alkynyl substituted with a SiHR22R23 group, or a C2-C10 alkynyl substituted with a —Si(R22)x(R23)y(R24)z group;
- wherein each R22 group is independently selected from the group consisting of a branched or unbranched, substituted or unsubstituted C1-C10 alkyl group, a branched or unbranched, substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted C2-C20 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, and a substituted or unsubstituted C6-C20 cycloalkylalkylene group;
- each R23 group is independently selected from the group consisting of a branched or unbranched, substituted or unsubstituted C1-C10 alkyl group, a branched or unbranched, substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C20 cycloalkyl group, and a substituted or unsubstituted C6-C20 cycloalkylalkylene group;
- R24 is independently selected from the group consisting of hydrogen, a branched or unbranched, substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted C2-C20 cycloalkyl group, a substituted or unsubstituted C6-C20 cycloalkylalkylene group, a substituted C5-C20 aryl group, a substituted or unsubstituted C6-C20 arylalkylene group, an acetyl group, a substituted or unsubstituted C3-C20 heterocyclic ring comprising at least one of O,N,S and Se in the ring;
- wherein x=1 or 2;
- y=1 or 2;
- z=0 or 1;
- and (x+y+z)=3;
- wherein each of R15, R16, R18, R19 and R20 independently represent H or optionally substituted C1-C40 carbyl or hydrocarbyl group optionally comprising one or more heteroatoms;
- wherein R17 represents a halogen atom, H or optionally substituted C1-C40 carbyl or C1-C40 hydrocarbyl group optionally comprising one or more heteroatoms;
- wherein k and l are independently 0 or 1;
- wherein at least two of R1, R3, R4, R6, R7, R9, R10, and R12, are a bond, represented by *, to another monomer unit having the Formula (A) or (B);
- and
- wherein Ar1, Ar2 and Ar3, which may be the same or different, each represent, independently if in different repeat units, an optionally substituted C6-40 aromatic group (mononuclear or polynuclear), and
- wherein the composition has a permittivity at 1000 Hz of between 3 and 6.5, between 3.4 and 8 or between 4 and 6.5.
45 more elements
An ink comprising a Polycyclic Aromatic Hydrocarbon Copolymer (PAHC), wherein the PAHC is a random copolymer comprising at least one BXBX monomer unit having the Formula (A) and at least one monomer unit having the Formula (B):
- wherein
- Y1 and Y2 are independently S or Se;
- k and l are independently 0 or 1
- wherein each of R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11 and R12, which may be the same or different, independently represents hydrogen;
- a branched or unbranched, substituted or unsubstituted C1-C40 alkyl group;
- a branched or unbranched, substituted or unsubstituted C2-C40 alkenyl group;
- a branched or unbranched, substituted or unsubstituted C2-C40 alkynyl group;
- an optionally substituted C3-C40 cycloalkyl group;
- an optionally substituted C6-C40 aryl group;
- an optionally substituted C1-C40 heterocyclic group;
- an optionally substituted C1-C40 heteroaryl 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)NR15R16);
- a carbonyl group (—C(═O)—R17);
- a carboxyl group (—CO2R18) a cyanate group (—OCN);
- an isocyano group (—NC);
- an isocyanate group (—NCO);
- a thiocyanate group (—SCN) or a thioisocyanate group (—NCS);
- an optionally substituted amino group;
- a hydroxy group;
- a nitro group;
- a CF3 group;
- a halo group (C1, Br, F, I);
- —SR19;
- —SO3H;
- —SO2R20;
- —SF5;
- an optionally substituted silyl group;
- a C2-C10 alkynyl group substituted with a SiH2R22 group, a C2-C10 alkynyl substituted with a SiHR22R23 group, or a C2-C10 alkynyl substituted with a —Si(R22)x(R23)x(R24)z group;
- wherein each R22 group is independently selected from the group consisting of a branched or unbranched, substituted or unsubstituted C1-C10 alkyl group, a branched or unbranched, substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted C2-C20 cycloalkyl group, a substituted or unsubstituted C2-C10 alkenyl group, and a substituted or unsubstituted C6-C20 cycloalkylalkylene group;
- each R23 group is independently selected from the group consisting of a branched or unbranched, substituted or unsubstituted C1-C10 alkyl group, a branched or unbranched, substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted C2-C10 alkenyl group, a substituted or unsubstituted C2-C20 cycloalkyl group, and a substituted or unsubstituted C6-C20 cycloalkylalkylene group;
- R24 is independently selected from the group consisting of hydrogen, a branched or unbranched, substituted or unsubstituted C2-C10 alkynyl group, a substituted or unsubstituted C2-C20 cycloalkyl group, a substituted or unsubstituted C6-C20 cycloalkylalkylene group, a substituted C5-C20 aryl group, a substituted or unsubstituted C6-C20 arylalkylene group, an acetyl group, a substituted or unsubstituted C3-C20 heterocyclic ring comprising at least one of O, N, S and Se in the ring;
- wherein x=1 or 2;
- y=1 or 2;
- z=0 or 1;
- and (x+y+z)=3;
- wherein each of R15, R16, R18, R19 and R20 independently represent H or optionally substituted C1-C40 carbyl or hydrocarbyl group optionally comprising one or more heteroatoms;
- wherein R17 represents a halogen atom, H or optionally substituted C1-C40 carbyl or C1-C40 hydrocarbyl group optionally comprising one or more heteroatoms;
- wherein k and l are independently 0 or 1;
- wherein at least two of R1, R3, R4, R6, R7, R9, R10, and R12, are a bond, represented by *, to another monomer unit having the Formula (A) or (B);
- and
- wherein Ar1, Ar2 and Ar3, which may be the same or different, each represent, independently if in different repeat units, an optionally substituted C6-40 aromatic group (mononuclear or polynuclear).
44 more elements
Dependencies are inferred from the claim text.