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  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
  • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
  • C07D471/06—Peri-condensed systems
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  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
  • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
  • C07D221/04—Ortho- or peri-condensed ring systems
  • C07D221/18—Ring systems of four or more rings
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  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B57/00—Other synthetic dyes of known constitution
  • C09B57/08—Naphthalimide dyes; Phthalimide dyes
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  • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
  • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
  • H10K10/40—Organic transistors
  • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
  • H10K10/462—Insulated gate field-effect transistors [IGFETs]
  • H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
  • H10K10/486—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions the channel region comprising two or more active layers, e.g. forming pn heterojunctions
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  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K50/00—Organic light-emitting devices
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  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
  • H10K85/60—Organic compounds having low molecular weight
  • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
  • H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
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  • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
  • C09K2211/10—Non-macromolecular compounds
  • C09K2211/1018—Heterocyclic compounds
  • C09K2211/1025—Heterocyclic compounds characterised by ligands
  • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
  • H10K10/40—Organic transistors
  • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
  • H10K10/462—Insulated gate field-effect transistors [IGFETs]
  • H10K10/464—Lateral top-gate IGFETs comprising only a single gate
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
  • H10K10/40—Organic transistors
  • H10K10/46—Field-effect transistors, e.g. organic thin-film transistors [OTFT]
  • H10K10/462—Insulated gate field-effect transistors [IGFETs]
  • H10K10/466—Lateral bottom-gate IGFETs comprising only a single gate

Definitions

• Organic semiconducting materials can be used in electronic devices such as organic photovol- taic (OPV) cells, organic field-effect transistors (OFETs) and organic light emitting diodes (OLEDs).
• OOV organic photovol- taic
• OFET organic field-effect transistors
• OLED organic light emitting diodes
• the organic semiconducting material-based devices show high charge carrier mobility and high stability, in particular towards oxi- dation, under ambient conditions.
• the organic semiconducting materials are compatible with liquid processing techniques as liquid processing techniques are convenient from the point of pro- cessability, and thus allow the production of low cost organic semiconducting material-based electronic devices.
• liquid processing techniques are also compatible with plastic substrates, and thus allow the production of light weight and flexible organic semiconducting material-based electronic devices.
• Perylene bisimide-based organic semiconducting materials suitable for use in electronic devices are known in the art.
• OFET organic thin film transistor
• the organic semiconductor film is formed of pentacene.
• the organic acceptor film is formed of at least one electron withdrawing material selected from a long list of compounds, including N,N'-bis(di-ferf-butyphenyl)-3,4,9,10-perylenedicarboximide.
• US 7,326,956 B2 describes a thin film transitor comprising a layer of organic semiconductor material comprising tetracarboxylic diimide perylene-based compound having attached to each of the imide nitrogen atoms a carbocyclic or heterocyclic aromatic ring system substituted with one or more fluorine containing groups.
• the fluorine-containing N,N'-diaryl perylene-based tetracarboxylic diimide compound is represented by the following structure:
• a 1 and A 2 are independently carbocyclic and/or heterocyclic aromatic ring systems comprising at least one aromatic ring in which one or more hydrogen atoms are substituted with at least one fluorine-containing group.
• the perylene nucleus can be optionally substituted with up to eight independently selected X groups, wherein n is an integer from 0 to 8.
• the X substit- uent groups on the perylene can include a long list of substituents, including halogens such as fluorine or chlorine.
• WO 2007/093643 describes fluorinated rylenetetracarboxylic acid derivatives. Preferred pounds are of formula IBa
• R a and R b are independently from each other are H or an organic residue.
• WO 2008/063609 describes a compound having the following formula 1
• A, B, I, D, E, F, G and H are independently selected from a group of substituents, in- eluding, CH and CR a , wherein R a can be selected from a list of substituents, including halogen.
• A, B, I, D, E, F, G and H can be independently CH, C-Br or C-CN.
• WO 2009/024512 describes halogen-containing perylenetetracarboxylic acid derivatives, and in particular compound IBa
• residues R 11 , R 12 , R 13 , R 14 , R 21 , R 22 , R 23 and R 24 are CI and/or F, wherein 1 or 2 of the residues R 11 , R 12 , R 13 , R 14 , R 21 , R 22 , R 23 and R 24 can be CN, and/or , and wherein 1 of the residues R 11 , R 12 , R 13 , R 14 , R 21 , R 22 , R 23 and R 24 can be H, and
• R a and R b are independently from each other are H or an organic residue.
• the perylene-based semiconducting compound of the present invention is of formula
• R 1 and R 2 are independently from each other selected from the group consisting of H, Ci-30-alkyl optionally substituted with 1 to 30 substituents R a , C2-3o-alkenyl optionally substituted with 1 to 30 substituents R a , C2-3o-alkynyl optionally substituted with 1 to 30 substituents R a , C3-io-cycloalkyl optionally substituted with 1 to 10 substituents R b , Cs-io-cycloalkenyl option- ally substituted with 1 to 10 substituents R , 3-14 membered cycloheteroalkyl optionally substituted with 1 to 8 substituents R b , C6-i4-aryl optionally substituted with 1 to 8 substituents R c and 5-14 membered heteroaryl optionally substituted with 1 to 8 substituents R c , wherein
• R 3 , R 4 and R 5 at each occurrence are independently from each other selected from the group consisting of Ci-30-alkyl optionally substituted with 1 to 30 substituents R', C 2 -3o-alkenyl optionally substituted with 1 to 30 substituents R', C 2- 3o-alkynyl optionally substituted with 1 to 30 substituents R', C3-io-cycloalkyl optionally substituted with 1 to 10 substituents R", Cs-io-cycloalkenyl optionally substituted with 1 to 10 substituents R", 3-14 membered cycloheteroalkyi optionally substituted with 1 to 10 substituents R", C6-i4-aryl optionally substituted with 1 to 8 substituents R'" and 5-14 membered heteroaryl optionally substituted with 1 to 8 substituents R'",
• R s , R 7 and R 8 at each occurrence are independently from each other selected from the group consisting of Ci -3 o-alkyl, C 2 -3o-alkenyl, C 2-3 o-alkynyl, C3-io-cycloalkyl, C5-io-cycloalkenyl, 3-14 membered cycloheteroalkyl , C6-i4-aryl and 5-14 membered heteroaryl.
• Ci-10-alkyl and Ci-30-alkyl can be branched or unbranched.
• Examples of Ci-10-alkyl are methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, fert-butyl, n-pentyl, neopentyl, isopentyl, n-(1 -ethyl)propyl, n-hexyl, n-heptyl, n-octyl, n-(2-ethyl)hexyl, n-nonyl and n-decyl.
• C3-8-alkyl examples include n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, fert-butyl, n-pentyl , neopentyl, isopentyl, n-(1-ethyl)propyl, n-hexyl, n-heptyl, n-octyl and n-(2-ethyl)hexyl.
• Ci-30-alkyl examples are Ci-10-alkyl, and n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-nonadecyl and n-icosyl (C 2 o), n-docosyl (C 22 ), n-tetracosyl (C 2 4), n-hexacosyl (C 2 s), n-octacosyl (C 2 e) and n-triacontyl (C30).
• C3- 2 5-alkyl branched at the C attached to the N of formula I are isopropyl, sec-butyl, n-(1-methyl)propyl, n-(1 - ethyl)propyl, n-(1-methyl)butyl, n-(1 -ethyl)butyl, n-(1 -propyl) butyl, n-(1-methyl)pentyl, n-(1 - ethyl)pentyl, n-(1 -propyl)pentyl, n-(1-butyl)pentyl, n-(1 -butyl)hexyl, n-(1-pentyl)hexyl, n-(1- hexyl)heptyl, n-(1-heptyl)octyl, n-(1-octyl)nonyl, n
• C 2 -3o-alkenyl can be branched or unbranched.
• Examples of C 2 -3o-alkenyl are vinyl, propenyl, cis-
• 3- pentenyl 4-pentenyl, 2-methyl-3-butenyl, hexenyl, heptenyl, octenyl, nonenyl and docenyl, linoleyl (Cie), linolenyl (Cie), oleyl (Cie), arachidonyl (C 2 o), and erucyl (C 22 ).
• C 2 - 3 o-alkynyl can be branched or unbranched.
• Examples of C 2 - 3 o-alkynyl are ethynyl, 2-propynyl, 2-butynyl, 3-butynyl, pentynyl, hexynyl, heptynyl , octynyl , nonynyl and decynyl, undecynyl , do- g
• C3-io-cycloalkyl are preferably monocyclic C3-io-cycloalkyls such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl, but include also polycyclic
• C3-io-cycloalkyls such as decalinyl, norbornyl and adamantyl.
• Cs-io-cycloalkenyl are preferably monocyclic Cs-io-cycloalkenyls such as cyclopen- tenyl, cyclohexenyl, cyclohexadienyl and cycloheptatrienyl, but include also polycyclic
• Examples of 3-14 membered cycloheteroalkyi are monocyclic 3-8 membered cycloheteroalkyi and polycyclic, for example bicyclic 7-12 membered cycloheteroalkyi.
• Examples of monocyclic 3-8 membered cycloheteroalkyi are monocyclic 5 membered cycloheteroalkyi containing one heteroatom such as pyrrolidinyl, 1-pyrrolinyl, 2-pyrrolinyl, 3-pyrrolinyl, tetrahydrofuryl, 2,3-dihydrofuryl, tetrahydrothiophenyl and 2,3-dihydrothiophenyl, monocyclic
• cycloheteroalkyi containing one heteroatom such as piperidyl, piperidino, tetrahy- dropyranyl, pyranyl, thianyl and thiopyranyl, monocyclic 6 membered cycloheteroalkyi containing two heteroatoms such as piperazinyl, morpholinyl and morpholino and thiazinyl, monocyclic 7 membered cycloheteroalkyi containing one hereoatom such as azepanyl, azepinyl, oxepanyl, thiepanyl, thiapanyl, thiepinyl, and monocyclic 7 membered cycloheteroalkyi containing two hereoatom such as 1 ,2-diazepinyl and 1 ,3-thiazepinyl.
• An example of a bicyclic 7-12 membered cycloheteroalkyi is decahydronaphthyl.
• C6-i4-aryl can be monocyclic or polycyclic.
• Examples of C6-i4-aryl are monocyclic C6-aryl such as phenyl, bicyclic C9-io-aryl such as 1-naphthyl, 2-naphthyl, indenyl, indanyl and tetrahydronaph- thyl, and tricyclic Ci2-i4-aryl such as anthryl, phenanthryl, fluorenyl and s-indacenyl.
• 5-14 membered heteroaryl can be monocyclic 5-8 membered heteroaryl, or polycyclic 7-14 membered heteroaryl, for example bicyclic 7-12 membered or tricyclic 9-14 membered heteroaryl.
• monocyclic 5-8 membered heteroaryl are monocyclic 5 membered heteroaryl containing one heteroatom such as pyrrolyl, furyl and thiophenyl, monocyclic 5 membered heteroaryl containing two heteroatoms such as imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, monocyclic 5 membered heteroaryl containing three heteroatoms such as
• 1 ,2,3-triazolyl, 1 ,2,4-triazolyl and oxadiazolyl monocyclic 5 membered heteroaryl containing four heteroatoms such as tetrazolyl, monocyclic 6 membered heteroaryl containing one heteroa- tom such as pyridyl, monocyclic 6 membered heteroaryl containing two heteroatoms such as pyrazinyl, pyrimidinyl and pyridazinyl, monocyclic 6 membered heteroaryl containing three heteroatoms such as 1 ,2,3-triazinyl, 1 ,2,4-triazinyl and 1 ,3,5-triazinyl, monocyclic / membered heteroaryl containing one heteroatom such as azepinyl, and monocyclic 7 membered heteroaryl containing two heteroatoms such as 1 ,2-diazepinyl.
• monocyclic 5 membered heteroaryl containing four heteroatoms such as
• bicyclic 7-12 membered heteroaryl examples include bicyclic 9 membered heteroaryl containing one heteroatom such as indolyl, isoindolyl, indolizinyl, indolinyl, benzofuryl, isobenzofuryl, ben- zothiophenyl and isobenzothiophenyl, bicyclic 9 membered heteroaryl containing two heteroatoms such as indazolyl, benzimidazolyl, benzimidazolinyl, benzoxazolyl, benzisooxazolyl, benzthiazolyl, benzisothiazolyl, furopyridyl and thienopyridyl, bicyclic 9 membered heteroaryl containing three heteroatoms such as benzotriazolyl, benzoxadiazolyl, oxazolopyridyl, isooxa- zolopyridyl, thiazolopyridyl, iso
• tricyclic 9-14 membered heteroaryls examples include dibenzofuryl, acridinyl, phenoxazinyl, 7H- cyclopenta[1 ,2-b:3,4-b']dithiophenyl and 4H-cyclopenta[2,1-b:3,4-b']dithiophenyl.
• halogen examples are -F, -CI, -Br and -I .
• Ci-30-alkoxy examples are methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, ferf-butoxy, n-pentoxy, neopentoxy, isopentoxy, hexoxy, n-heptoxy, n-octoxy, n-nonoxy, n-decoxy, n-undecoxy, n-dodecoxy, n-tridecoxy, n-tetradecoxy, n-pentadecoxy, n-hexadecoxy, n-heptadecoxy, n-octadecoxy and n-nonadecoxy.
• Examples of C2-5-alkylene are ethylene, propylene, butylene and pentylene.
• R 1 and R 2 are independently from each other selected from the group consisting of H , Ci-30-alkyl optionally substituted with 1 to 30 substituents R a , C2-3o-alkenyl optionally substituted with 1 to 30 substituents R a , C3-io-cycloalkyl optionally substituted with 1 to 10 substituents R b , and C6-i4-aryl optionally substituted with 1 to 8 substituents R c , wherein
• R 3 , R 4 and R 5 at each occurrence are independently from each other selected from the group consisting of Ci-30-alkyl optionally substituted with 1 to 30 substituents R', C 2 -3o-alkenyl optionally substituted with 1 to 30 substituents R', C3-io-cycloalkyl option- ally substituted with 1 to 10 substituents R", and Cs-i4-aryl optionally substituted with
• R s , R 7 and R 8 at each occurrence are independently from each other selected from the group consisting of Ci -3 o-alkyl, C 2 . 3 o-alkenyl, C 3 -io-cycloalkyl, and C6-i4-aryl.
• R 3 , R 4 and R 5 at each occurrence are independently from each other selected from the group consisting of Ci- 3 o-alkyl optionally substituted with 1 to 30 substituents R', C 2 . 3 o-alkenyl optionally substituted with 1 to 30 substituents R', C 3- io-cycloalkyl optionally substituted with 1 to 10 substituents R' ⁇ and C6-i4-aryl optionally substituted with 1 to 8 substituents R iH ,
• R 6 , R 7 and R 8 at each occurrence are independently from each other selected from the group consisting of Ci-30-alkyl, C 2 -3o-alkenyl, C3-io-cycloalkyl, and C6-i4-aryl.
• R 1 and R 2 are independently from each other C3- 2 5-alkyl branched at the C attached to the N of formula 1. Particular preferred is the compound of formula
• R 1 and R 2 are as defined above, which process comprises the steps of
• R 1 and R 2 are as defined above, and X is CI, Br or I, with a fluoride source.
• the fluoride source can be an alkali fluoride, such as potassium fluoride.
• the ratio of molequivalents fluoride source/compound of formula (5) is in the range of 1/1 to 30/1 , preferably in the range of 10/1 to 30/1.
• the reaction is usually performed at temperatures between 100 °C and 200 °C, preferably between 130 °C to 180 °C.
• the reaction is usually performed in a sealed reaction vessel.
• the reaction is usually performed in an aprotic solvent.
• aprotic solvents are ethers such as dioxane and diglyme (bis(2-methoxyethyl) ether) or mixtures thereof.
• X is preferably CI.
• the compounds of formula (5) can be prepared as described by G. Battagliari; C. Li, V. Enkel- mann, K. Mullen Org. Lett. 2011 , 13, 3012-3015, and G. Battagliari; Y. Zhao; C. Li, K. Mullen Org. Lett. 2011 , 13, 3399-3401.
• the compounds of formula (1 ) can be isolated by methods known in the art, such as column chromatography.
• an electronic device comprising the compound of formula (1 ) as semiconducting material.
• the electronic device is an organic field effect transistor (OFET).
• OFET organic field effect transistor
• an organic field effect transistor comprises a dielectric layer, a semiconducting layer and a substrate.
• an organic field effect transistor usually comprises a gate electrode and source/drain electrodes.
• An organic field effect transistor can have various designs.
• bottom-gate design The most common design of an organic field-effect transistor is the bottom-gate design. Examples of bottom-gate designs are shown in Figures 1.
• top-gate design Another design of an organic field-effect transistor is the top-gate design. Examples of top-gate designs are shown in Figure 2.
• the semiconducting layer comprises the semiconducting material of the present invention.
• the semiconducting layer can have a thickness of 5 to 500 nm, preferably of 10 to 100 nm, more preferably of 20 to 50 nm.
• the dielectric layer comprises a dielectric material.
• the dielectric material can be silicon dioxide, or, an organic polymer such as polystyrene (PS), poly(methylmethacrylate) (PMMA), poly(4-vinylphenol) (PVP), polyvinyl alcohol) (PVA), benzocyclobutene (BCB), or polyimide (PI).
• PS polystyrene
• PMMA poly(methylmethacrylate)
• PVP poly(4-vinylphenol)
• PVA polyvinyl alcohol
• BCB benzocyclobutene
• PI polyimide
• the dielectric layer can have a thickness of 10 to 2000 nm, preferably of 50 to 1000 nm, more preferably of 100 to 800 nm.
• the source/drain electrodes can be made from any suitable source/drain material, for example gold (Au) or tantalum (Ta).
• the source/drain electrodes can have a thickness of 1 to 100 nm, preferably from 5 to 50 nm.
• the gate electrode can be made from any suitable gate material such as highly doped silicon, aluminium (Al), tungsten (W), indium tin oxide, gold (Au) and/or tantalum (Ta).
• the gate electrode can have a thickness of 1 to 200 nm, preferably from 5 to 100 nm.
• the substrate can be any suitable substrate such as glass, or a plastic substrate such as poly- ethersulfone, polycarbonate, polysulfone, polyethylene terephthalate (PET) and polyethylene naphthalate (PEN).
• a combination of the gate electrode and the dielectric layer can also function as substrate.
• the organic field effect transistor can be prepared by methods known in the art.
• a bottom-gate organic field effect transistor can be prepared as follows:
• the gate electrode can be formed by depositing the gate material, for example highly doped silicon, on one side of the dielectric layer made of a suitable dielectric material, for example si- licium dioxide.
• the other side of the dielectric layer can be optionally treated with a suitable reagent, for example with hexamethyldisilazane (HMDS).
• Source/drain electrodes can be deposited on this side (the side which is optionally treated with a suitable reagent) of the dielectric layer for example by vapour deposition of a suitable source/drain material, for example tantalum (Ta) and/or gold (Au).
• the source/drain electrodes can then be covered with the semiconducting layer by solution processing, for example drop coating, a solution of the semiconducting material of the present invention in s suitable solvent, for example in chloroform.
• Also part of the invention is the use of the compound of formula (1 ) as semiconducting material.
• the advantage of the semiconducting materials of the present invention is the high solubility of these materials in solvents suitable for solution processing.
• the semiconducting materials of the present invention show acceptable charge carrier mobility.

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