WO2021078217A1 - Dérivé de tétracène, son procédé de préparation et son utilisation - Google Patents

Dérivé de tétracène, son procédé de préparation et son utilisation Download PDF

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WO2021078217A1
WO2021078217A1 PCT/CN2020/123012 CN2020123012W WO2021078217A1 WO 2021078217 A1 WO2021078217 A1 WO 2021078217A1 CN 2020123012 W CN2020123012 W CN 2020123012W WO 2021078217 A1 WO2021078217 A1 WO 2021078217A1
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acid
compound
reaction
alkyl
membered heteroaryl
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胡文平
舒志斌
董焕丽
王普
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中国科学院化学研究所
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Definitions

  • the invention belongs to the field of organic optoelectronics and semiconductor devices, and specifically relates to a naphthacene derivative and a preparation method and application thereof.
  • Naphthacene is composed of 4 benzene rings and its melting point is about 320°C. It has high thermal and light stability. It is less affected by external conditions such as water vapor and oxygen, and it is easy to form needles.
  • the crystals show a very regular fishbone arrangement. From the structural point of view, the field-effect mobility of crystals and films with fishbone-like arrangements of organic small molecules is often the highest. Therefore, tetracene should be an ideal field effect material.
  • Batlogg et al. of Bell Laboratory used naphthacene single crystal as the active layer and used the dual field effect to make an organic electric injection laser. The carrier mobility of the device reached 2cm 2 /V ⁇ s at room temperature.
  • topological conjugated benzene ring structure data materials such as pentacene and hexacene have also been synthesized and applied to the research of organic optoelectronic devices (Nat.Chem.,2020,12,63; Adv.Mater.,2007 ,5,688; Nat.Chem.,2017,9,Nat.Chem.,2012,4,574,etc.), but this type of material has serious problems such as poor light stability, which also limits its application research. Therefore, how to achieve a multi-fused ring conjugated molecular structure with good stability and film-forming properties is of vital importance to scientific research and device application research.
  • the lateral derivatization of the conjugated ring skeleton is of great significance for realizing the further expansion of the conjugation system and obtaining application materials with better performance, and provides an effective way to solve the above problems.
  • anthracene and pentacene have obtained considerable development and sufficient reports in the side modification and derivatization and their device applications, which are attributed to the ease of organic synthesis and the maturity of device preparation.
  • device research still remains on a few materials modified at fixed sites, especially those derived from both the 2- and 8-positions of naphthacene.
  • the present invention provides a 2,8-disubstituted naphthacene derivative represented by the following formula (I),
  • R are the same or different, and are independently selected from halogen, the following groups optionally substituted by one, two or more RS: C 6-20 aryl, 5-20 membered hetero Aryl, 5-20 membered heteroaryl and 5-20 membered heteroaryl, 5-20 membered heteroaryl and 5-20 membered heteroaryl and 5-20 membered heteroaryl, even two (C 6-20 Aryl and C 3-20 cycloalkyl and C 6-20 aryl) group, C 1-40 alkyl, C 3-20 cycloalkyl, 5-20 membered heterocyclic group, C 1-40 alkoxy , C 1-40 alkylthio;
  • the RS is selected from halogen, CN, C 1-40 alkyl, halogenated C 1-40 alkyl, -N (C 6-20 aryl) 2 , C 3-20 cycloalkyl, 3-20 membered hetero cycloalkyl group, -N (C 1- 40 alkyl) 2; optionally substituted by one, two or more C 1-40 alkyl substituted with halo radicals as follows: C 6-20 aryl group, 5- 20-membered heteroaryl.
  • R is selected from halogen, and the following groups optionally substituted by one, two or more RS: C 6-14 aryl, 5-14 membered heteroaryl Group, 5-14 membered heteroaryl and 5-14 membered heteroaryl, 5-14 membered heteroaryl and 5-14 membered heteroaryl and 5-14 membered heteroaryl, even two (C 6-14 aryl C 3-12 cycloalkyl and C 6-14 aryl) group, C 1-12 alkyl, C 1-12 alkoxy, C 1-12 alkylthio;
  • the RS is selected from halogen, CN, C 1-10 alkyl, halogenated C 1-10 alkyl, -N (C 6-14 aryl) 2 , C 3-10 cycloalkyl, 3-10 membered hetero Cyclic group, -N(C 1- 10 alkyl) 2 ; the following groups optionally substituted by one, two or more substituted halogenated C 1-10 alkyl groups: C 6-14 aryl, 5- 14-membered heteroaryl.
  • R is selected from Br, phenyl, 1-naphthyl, 2-naphthyl, thienyl, furyl, 2-anthryl, 5-anthryl, 2-fluorenyl, 3-fluorene Group, 1-dibenzofuranyl, 3-dibenzofuranyl, 3-dibenzopyrrolyl, N-dibenzopyrrolyl, 1-dibenzothienyl, 3-dibenzothienyl, 1-pyrazinyl, 1-thiazolyl, 2-phenazinyl, 1-quinoxalinyl, 9-fluorenone-2-yl, 7-quinolinyl,
  • RS is selected from fluorine, chlorine, bromine, CN, methyl, ethyl, n-hexyl, perfluoro-n-hexyl, phenyl, 3,4,5-tris(trifluoromethyl)-phenyl, 3,5- Bis(trifluoromethyl)-phenyl, 1-furyl, 1-thienyl, 4-trifluoromethyl-furyl, 4-trifluoromethyl-thienyl, N-carbazolyl, -N( Phenyl) 2 , trifluoromethyl.
  • the compound of formula (I) is selected from the following structures,
  • the present invention also provides a method for preparing the 2,8-dibromotetracene, which includes the following steps:
  • step S2 The compound 6-bromo-1,4-epoxy-1,4-dihydronaphthalene, 4-bromobenzocyclobutane and additive 1 prepared in step S1) are reacted in solvent 3 to obtain products 2,8 -Dibromo-5,12-epoxy-5,5a,6,11,11a,12-hexahydrotetracene;
  • step S3 Put the compound 2,8-dibromo-5,12-epoxy-5,5a,6,11,11a,12-hexahydrotetracene and acid 2 prepared in step S2) in solvent 4 and heat to reflux In the reaction, the resulting product and the additive 2 are heated and refluxed in the solvent 5 to obtain 2,8-dibromotetracene;
  • step S1) the acid 1 is selected from inorganic acids
  • the nitrous acid compound is selected from at least one of tert-butyl nitrite, isoamyl nitrite, sodium nitrite, and potassium nitrite;
  • step S2) the additive 1 is selected from inorganic bases
  • step S3) the acid 2 is selected from inorganic acid or organic acid;
  • step S3) the additive 2 is selected from oxidizing agents.
  • the acid 1 is at least one of inorganic acids such as hydrochloric acid, sulfuric acid, phosphoric acid, boron trifluoride, phosphorus pentafluoride, etc., specifically hydrochloric acid or boron trifluoride;
  • the solvent 1 is an alcohol solvent such as methanol, ethanol, propanol, isopropanol, butanol, ethylene glycol monomethyl ether, etc., specifically ethanol or ethylene glycol.
  • Alcohol solvent such as methanol, ethanol, propanol, isopropanol, butanol, ethylene glycol monomethyl ether, etc., specifically ethanol or ethylene glycol.
  • Monomethyl ether such as methanol, ethanol, propanol, isopropanol, butanol, ethylene glycol monomethyl ether, etc., specifically ethanol or ethylene glycol.
  • Monomethyl ether such as methanol, ethanol, propanol, isopropanol, butanol, ethylene glycol monomethyl ether, etc., specifically ethanol or ethylene glycol.
  • Monomethyl ether solvent such as methanol, ethanol, propanol, isopropanol, butanol, ethylene glycol monomethyl ether, etc
  • the solvent 2 is ethers such as diethyl ether, methyl isopropyl ether, diisopropyl ether, butyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, dioxane, etc.
  • Solvents or aromatic hydrocarbon solvents such as benzene, toluene, xylene, chlorobenzene, fluorobenzene, bromobenzene, chloronaphthalene, or chloroform, methylene chloride, dichloroethane, trichloroethane, dibromoethane, Alkane solvents such as dodecane and hexadecane, specifically tetrahydrofuran or chlorobenzene or dichloroethane;
  • aromatic hydrocarbon solvents such as benzene, toluene, xylene, chlorobenzene, fluorobenzene, bromobenzene, chloronaphthalene, or chloroform, methylene chloride, dichloroethane, trichloroethane, dibromoethane, Alkane solvents such as dodecane and hexadecane, specifically tetrahydrofuran or chlorobenzene
  • the molar ratio of the compound 2-amino-5-bromobenzoic acid, acid 1 and nitrous acid compound is 1:(0.01-100):(0.01-100), Preferably, it is 1:(1 ⁇ 5):(1 ⁇ 5), and specifically can be 1:1:1 or 1:2:3;
  • the molar ratio of the furan to the starting material 2-amino-5-bromobenzoic acid is 1:(0.01-100), preferably 1:(0.1-1), Specifically 1:1 or 1:0.2;
  • the low-temperature reaction temperature is -200-10°C, preferably -78-10°C; the heating reflux temperature range may be 30-300°C.
  • the additive 1 is potassium carbonate, potassium bicarbonate, sodium carbonate, sodium bicarbonate, potassium acetate, sodium acetate, sodium citrate, specifically sodium carbonate or potassium acetate;
  • the solvent 3 is ether, methyl isopropyl ether, diisopropyl ether, butyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, dioxane and other ethers Solvents, or aromatic hydrocarbon solvents such as benzene, toluene, xylene, chlorobenzene, fluorobenzene, bromobenzene, chloronaphthalene, or chloroform, methylene chloride, dichloroethane, trichloroethane, dibromoethane, Alkane solvents such as dodecane and hexadecane, specifically isoamyl ether, dichlorobenzene or dodecane;
  • step S2 the molar ratio of the compound 6-bromo-1,4-epoxy-1,4-dihydronaphthalene, 4-bromobenzocyclobutane and additive 1 is 1. :(0.01-100):(0.01-100), preferably 1:(0.5-3):(0.01-1), specifically 1:0.9:0.3 or 1:1.1:0.2;
  • the heating and reflux temperature range is 30-300°C.
  • the acid 2 is an inorganic acid such as hydrochloric acid, sulfuric acid, phosphoric acid, or acetic acid, trifluoroacetic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid or its hydrate, pyridine Organic acids such as p-toluenesulfonate, specifically hydrochloric acid or p-toluenesulfonic acid monohydrate;
  • the solvent 4 is ethers such as ether, methyl isopropyl ether, diisopropyl ether, butyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, dioxane, etc.
  • Solvents or aromatic hydrocarbon solvents such as benzene, toluene, xylene, chlorobenzene, fluorobenzene, bromobenzene, chloronaphthalene, or chloroform, methylene chloride, dichloroethane, trichloroethane, dibromoethane, Alkane solvents such as dodecane and hexadecane, or acid anhydride solvents such as acetic anhydride, trifluoromethanesulfonic anhydride, or trifluoroacetic anhydride, specifically dioxane or toluene or dichloroethane or acetic anhydride;
  • aromatic hydrocarbon solvents such as benzene, toluene, xylene, chlorobenzene, fluorobenzene, bromobenzene, chloronaphthalene, or chloroform, methylene chloride, dichloroethane, trichloroethan
  • the additive 2 is oxygen, benzoquinone, tetrachlorobenzoquinone, dichlorodicyanobenzoquinone (DDQ), trichlorourea cyanide, bromine, iodine, bromosuccinate Oxidizers such as imide and iodosuccinimide, or catalysts such as activated carbon and palladium on carbon, specifically DDQ or palladium on carbon;
  • the solvent 5 may be ether, methyl isopropyl ether, diisopropyl ether, butyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, dioxane and other ethers.
  • Solvents can be aromatic hydrocarbon solvents such as benzene, toluene, xylene, chlorobenzene, fluorobenzene, bromobenzene, chloronaphthalene, or can be chloroform, dichloromethane, dichloroethane, trichloroethane, dibromide Alkane solvents such as ethane, dodecane, hexadecane, etc., specifically ethylene glycol dimethyl ether, benzene or carbon tetrachloride;
  • aromatic hydrocarbon solvents such as benzene, toluene, xylene, chlorobenzene, fluorobenzene, bromobenzene, chloronaphthalene, or can be chloroform, dichloromethane, dichloroethane, trichloroethane, dibromide Alkane solvents such as ethane, dodecane, hexadecane, etc., specifically
  • step S3) the compound 2,8-dibromo-5,12-epoxy-5,5a,6,11,11a,12-hexahydrotetracene and acid 2
  • the molar ratio is 1:(0.01-100), preferably 1:(0.5-25), and specifically may be 1:25 or 1:0.5;
  • step S3 the compound 2,8-dibromo-5,12-epoxy-5,5a,6,11,11a,12-hexahydrotetracene and additive 2
  • the molar ratio is 1:(0.01-100), preferably 1:(0.02-5), specifically 1:0.5 or 1:2;
  • the heating and reflux temperature range may be 30-320°C.
  • the present invention also provides the application of the 2,8-dibromotetracene described above in the preparation of the 2,8-disubstituted naphthacene derivatives represented by formula (I).
  • the present invention also provides a preparation method of 2,8-disubstituted naphthacene derivatives represented by formula (I), which comprises the following steps:
  • 2,8-Dibromotetracene reacts with compound X-R to obtain 2,8-disubstituted tetracene derivatives represented by formula (I),
  • R has the above-mentioned definition
  • X is selected from a leaving group
  • 2,8-dibromotetracene is preferably prepared by the above method.
  • X is selected from halogen, boric acid, boric acid ester, alkyl tin, alkyl silicon, magnesium, zinc, and the like.
  • the reaction is the following reactions: Suzuki reaction, Stille reaction, Heck reaction, Sonogashira reaction, Hiyama reaction, Kumada reaction, Negishi reaction, Glaser-Eglinton reaction, Claisen-Schmidt reaction, Buchwald-Hartwig reaction.
  • the reaction is carried out in the presence of a catalytic system composed of a palladium complex or a palladium salt and a phosphine ligand;
  • the palladium complex refers to tetrakis (triphenylphosphine) palladium, dichlorodi (triphenylphosphine) palladium, dichlorodi (allyl) palladium, tris (dibenzylidene acetone) palladium, 1 ,1'-bis(diphenylphosphino)ferrocene]palladium dichloride, 1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium dichloromethane complex or others Palladium complexes suitable for Suzuki reaction;
  • the palladium salt refers to palladium metal salts suitable for Suzuki reaction such as palladium acetate, palladium trifluoroacetate, palladium chloride, palladium acetylacetonate, etc.;
  • the phosphine ligand refers to triphenylphosphine, tricyclohexylphosphine, AmPhos, MePhos, TrippyPhos, SPhos, tBuXPhos, XPhos, QPhos, RuPhos, DPEPhos, XantPhos, BINAP, DPPF, DPPP, DTBPF, DPPBZ, vBRIDP, cBRIDP Such as phosphine ligands suitable for Suzuki reaction.
  • the preparation method of the 2,8-disubstituted naphthacene derivative represented by formula (I) further includes the preparation method of 2,8-dibromotetracene as described above.
  • the present invention also provides the use of 2,8-disubstituted naphthacene derivatives represented by formula (I), which are used to prepare organic semiconductor devices, electronic devices, electroluminescence devices, biosensor devices, and photonic devices Or organic spin devices and related fields.
  • formula (I) 2,8-disubstituted naphthacene derivatives represented by formula (I), which are used to prepare organic semiconductor devices, electronic devices, electroluminescence devices, biosensor devices, and photonic devices Or organic spin devices and related fields.
  • the organic semiconductor device is selected from organic field effect transistor OFETs and optoelectronic devices based on organic field effect transistors.
  • the organic semiconductor layer of the organic semiconductor device includes a 2,8-disubstituted naphthacene derivative represented by formula (I).
  • the present invention provides a class of 2,8-disubstituted naphthacene derivatives.
  • This class of compounds has 6 or more condensed ring conjugated structure features, but due to the free carbon-carbon single bond in its conjugated structure Rotational characteristics make this type of material have many unique characteristics: On the one hand, this type of compound can avoid the problem of poor stability of traditional planar conjugated fused ring polyacene materials (such as pentacene and hexacene) and perform well.
  • this type of compound can avoid the serious fluorescence quenching characteristics of traditional tetracene, pentacene, hexacene and rubrene and other condensed ring material systems, and show more excellent emission spectra. , Even in the crystal state, it can still exhibit strong and bright fluorescence emission characteristics.
  • the compound material also exhibits excellent film-forming characteristics. Through the modification of different substrates, the crystalline properties of the film can be effectively mentioned, and it has excellent molecular arrangement, which is very conducive to high Obtaining performance optoelectronic devices.
  • the preparation route adopted by the present invention is simple, and it is easy to synthesize and obtain various types of substituted naphthacene derivatives.
  • the post-processing steps of intermediates are reduced.
  • Improve the synthesis efficiency, shorten the preparation time, and the cost is relatively low.
  • the total yield of the synthesis route reaches ⁇ 50%, which is very suitable for the laboratory's high-volume preparation.
  • halogen refers to F, Cl, Br, and I. In other words, F, Cl, Br, and I can be described as “halogen" in this specification.
  • C 1-40 alkyl should be understood to mean a linear or branched saturated monovalent hydrocarbon group having 1 to 40 carbon atoms, preferably a C 1-10 alkyl group.
  • C 1-10 alkyl should be understood to preferably mean a linear or branched saturated monovalent hydrocarbon group having 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10 carbon atoms.
  • the alkyl group is, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, 2-methylbutyl, 1-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, neopentyl, 1,1-dimethylpropyl, 4-methylpentyl, 3-methylpentyl Group, 2-methylpentyl, 1-methylpentyl, 2-ethylbutyl, 1-ethylbutyl, 3,3-dimethylbutyl, 2,2-dimethylbutyl, 1,1-dimethylbutyl, 2,3-dimethylbutyl, 1,3-dimethylbutyl, 1,2-dimethylbutyl, etc.
  • the group has 1, 2, 3, 4, 5, 6, carbon atoms ("C 1-6 alkyl”), such as methyl, ethyl, propyl, butyl, isopropyl , Isobutyl, sec-butyl, tert-butyl, more specifically, the group has 1, 2 or 3 carbon atoms ("C 1-3 alkyl”), such as methyl, ethyl, n-propyl ⁇ or isopropyl.
  • C 1-3 alkyl such as methyl, ethyl, n-propyl ⁇ or isopropyl.
  • C 1-40 alkyl refers to C 1-40 alkyl-O-, where C 1-40 alkyl has the definition as described above.
  • C 3-20 cycloalkyl used in the present invention means a saturated hydrocarbon ring, which may include a fused or bridged polycyclic ring system.
  • the cycloalkyl group preferably has 3 to 12 carbon atoms in its ring structure.
  • the cycloalkyl group has 3, 4, 5 or 6 carbon atoms in its ring structure.
  • C 3-6 cycloalkyl means a group such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl.
  • 3-20 membered heterocyclic group means a saturated monovalent monocyclic or bicyclic hydrocarbon ring containing 1-5 heteroatoms independently selected from N, O and S, preferably “3-10 membered heterocyclic group” ".
  • the term “3-10 membered heterocyclic group” means a saturated monovalent monocyclic or bicyclic hydrocarbon ring containing 1-5, preferably 1-3 heteroatoms selected from N, O and S.
  • the heterocyclic group may be connected to the rest of the molecule through any of the carbon atoms or the nitrogen atom (if present).
  • the heterocyclic group may include but is not limited to: 4-membered ring, such as azetidinyl, oxetanyl; 5-membered ring, such as tetrahydrofuranyl, dioxolyl, pyrrole Alkyl, imidazolidinyl, pyrazolidinyl, pyrrolinyl; or 6-membered ring, such as tetrahydropyranyl, piperidinyl, morpholinyl, dithiaalkyl, thiomorpholinyl, piperazinyl Or trithiaalkyl; or 7-membered ring, such as diazeppanyl.
  • 4-membered ring such as azetidinyl, oxetanyl
  • 5-membered ring such as tetrahydrofuranyl, dioxolyl, pyrrole Alkyl, imidazolidinyl, pyrazolidinyl, pyrrol
  • the heterocyclic group may be benzo-fused.
  • the heterocyclic group may be bicyclic, such as but not limited to a 5, 5-membered ring, such as hexahydrocyclopenta[c]pyrrole-2(1H)-yl ring, or a 5, 6-membered bicyclic ring, such as hexahydropyrrole And [1,2-a]pyrazine-2(1H)-yl ring.
  • the ring containing the nitrogen atom may be partially unsaturated, that is, it may contain one or more double bonds, such as but not limited to 2,5-dihydro-1H-pyrrolyl, 4H-[1,3,4]thiadi Azinyl, 4,5-dihydrooxazolyl or 4H-[1,4]thiazinyl, or it may be benzo-fused, such as but not limited to dihydroisoquinolinyl.
  • the heterocyclic group is non-aromatic.
  • C 6-20 aryl should be understood to mean a monovalent aromatic or partially aromatic monocyclic, bicyclic or tricyclic hydrocarbon ring with 6 to 20 carbon atoms, preferably “C 6-14 aryl”.
  • the term “C 6-14 aryl” should be understood as preferably meaning a monocyclic, bicyclic or partially aromatic monocyclic or partially aromatic monocyclic or partially aromatic having 6, 7, 8, 9, 10, 11, 12, 13 or 14 carbon atoms
  • a tricyclic hydrocarbon ring (“C 6-14 aryl"), especially a ring having 6 carbon atoms (“C 6 aryl”), such as phenyl; or biphenyl, or one having 9 carbon atoms Ring (“C 9 aryl”), such as indanyl or indenyl, or a ring with 10 carbon atoms (“C 10 aryl”), such as tetrahydronaphthyl, dihydronaphthyl or naphthyl, Either a ring having 13 carbon atoms ("
  • 5-20 membered heteroaryl should be understood to include such a monovalent monocyclic, bicyclic or tricyclic aromatic ring system which has 5-20 ring atoms and contains 1-5 independently selected from N, O And S heteroatoms, for example "5-14 membered heteroaryl".
  • the term “5-14 membered heteroaryl” should be understood to include monovalent monocyclic, bicyclic or tricyclic aromatic ring systems having 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14 ring atoms, especially 5 or 6 or 9 or 10 carbon atoms, and it contains 1-5, preferably 1-3 heteroatoms each independently selected from N, O and S and, additionally in each case The bottom can be benzo-fused.
  • the heteroaryl group is selected from thienyl, furyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, triazolyl, thiol Diazolyl, thio-4H-pyrazolyl, etc.
  • heterocyclic group, heteroaryl group or heteroarylene group includes all possible isomeric forms thereof, such as positional isomers thereof. Therefore, for some illustrative non-limiting examples, pyridinyl or pyridinylene includes pyridin-2-yl, pyridin-2-yl, pyridin-3-yl, pyridin-3-yl, pyridin-4-yl And pyridin-4-yl; thienyl or thienylene includes thiophen-2-yl, thiophen-2-yl, thiophen-3-yl, and thiophen-3-yl.
  • Figure 1 shows the equipment used in physical vapor transport to purify compounds, where A is the evaporation section; B is the deposition zone;
  • Figure 2 is a structural diagram of the devices prepared in Examples 4 and 5;
  • FIG. 3 is a diagram of a thin film device of the benzene derivative of naphthacene shown in formula 2;
  • Fig. 5 is a graph showing the transfer and output of the thiophene derivative of naphthacene shown in formula 5;
  • Fig. 6 is an AFM spectrum of the thin film device of the thiophene derivative of naphthacene shown in formula 5;
  • Fig. 7 is a transfer diagram of the naphthacene furan derivative thin film device shown in formula 6;
  • Fig. 8 is an output curve of the naphthacene furan derivative thin film device shown in formula 6;
  • the left picture in FIG. 9 is the ultraviolet absorption spectrum of the furan derivative of naphthacene shown in formula 6; the right picture is the ultraviolet absorption spectrum of the furan derivative of naphthacene shown in formula 5;
  • FIG. 10 is a transfer curve of a single crystal device of a naphthacene derivative represented by formula 2;
  • FIG. 11 is an output curve of a single crystal device of a naphthacene derivative shown in formula 2;
  • FIG. 12 is an atomic force scanning microscope image of a tetracene derivative (DPT) thin film device shown in formula 2;
  • Figure 13 is an X-ray diffraction diagram of the benzene derivative of naphthacene represented by formula 2;
  • Fig. 14 is an ultraviolet photoelectron spectrogram of the benzene derivative of naphthacene shown in formula 2;
  • FIG. 15 is an ultraviolet and fluorescence spectrum diagram of the benzene derivative of naphthacene shown in formula 2;
  • 16 is a real microscope photograph of a single crystal device prepared by the benzene derivative of naphthacene shown in formula 2;
  • Figure 17 is a single crystal transfer diagram of the furan derivative of naphthacene represented by formula 6;
  • FIG. 19 is a diagram of a single crystal device of the benzene derivative of naphthacene represented by Formula 2.
  • FIG. 21 is the stability data of continuous operation of the single crystal transistor device of naphthacene derivative represented by formula 2.
  • FIG. 22 is a study on the film-forming characteristics of the benzene derivative material of naphthacene represented by Formula 2.
  • Figure 23 shows the film-forming characteristics of the benzene derivative materials of naphthacene represented by formulas 4 (left) and 5 (right)
  • Figure 24 shows the structure data of the benzene derivative of naphthacene shown in formula 2 (a) single crystal simulated XRD diffraction data (bottom) and XRD experimental data from the obtained crystalline state, (b) single crystal packing mode data graph , Indicating that the material exhibits a typical herringbone accumulation pattern.
  • Fig. 25 is a bright-field photograph and ultraviolet fluorescence photograph of the benzene derivative material of naphthacene shown in Formula 2 in PMMA.
  • FIG. 26 is a data diagram of the luminescence performance of the benzene derivative material of naphthacene shown in formula 2 (emission of brown yellow (excitation wavelength 425nm), bright yellow (excitation wavelength 515nm) and red (excitation wavelength 590nm) light at different excitation wavelengths, respectively ).
  • FIG. 27 is a performance test diagram of a photoelectric device of a benzene derivative of naphthacene shown in formula 2.
  • the invention provides a synthetic route for efficiently preparing 2,8-dibromotetracene.
  • the compound represented by formula (I) is prepared by reacting 2,8-dibromotetracene with compound R-X.
  • Suitable compounds R-X are commercially available in many cases, and the starting compounds detailed in the examples can be obtained by known methods, so this information can be referred to.
  • X is a leaving group, for example, X is selected from D, NMe 2 , halogen, boric acid, boric acid ester, alkyl tin, silicon alkyl, magnesium, zinc and the like.
  • the compound 2,8-dibromotetracene, the preparation method includes the following steps:
  • the acid 1 can be an inorganic acid such as hydrochloric acid, sulfuric acid, phosphoric acid, boron trifluoride, phosphorus pentafluoride, etc., specifically it can be hydrochloric acid or boron trifluoride;
  • the nitrous acid compound can be Compounds such as tert-butyl nitrate, isoamyl nitrite, sodium nitrite, potassium nitrite, etc., specifically may be isoamyl nitrite;
  • the solvent 1 may be methanol, ethanol, propanol, isopropanol, butanol, Alcoholic solvents such as ethylene glycol monomethyl ether, specifically ethanol or ethylene glycol monomethyl ether;
  • the solvent 2 can be ethyl ether, methyl isopropyl ether, diisopropyl ether, butyl ether, ethylene glycol Ether solvents such as dimethyl ether, tetrahydrofuran,
  • Alkane solvents such as chloroethane, trichloroethane, dibromoethane, dodecane, hexadecane, etc., considering the three solvents, specifically tetrahydrofuran or chlorobenzene or dichloroethane; the compound 2-
  • the molar ratio of amino-5-bromobenzoic acid, acid 1 and nitrous acid compound is 1:(0.01-100):(0.01-100), specifically it can be 1:1:1 or 1:2:3;
  • the molar ratio of furan to the starting material 2-amino-5-bromobenzoic acid is 1: (0.01-100), specifically 1:1 or 1:0.2;
  • the low temperature range is -200-10°C, specifically It can be -10°C or 1°C;
  • the heating reflux means that the heating temperature is close to or higher than the boiling point of the reaction solvent under normal pressure, and the temperature range can be 30-1000°C, and in addition to the autoclave, the reaction vessel may
  • the additive 1 can be a weak base such as potassium carbonate, potassium bicarbonate, sodium carbonate, sodium bicarbonate, potassium acetate, sodium acetate, sodium citrate, etc., specifically sodium carbonate or potassium acetate;
  • Solvent 3 can be ether, methyl isopropyl ether, diisopropyl ether, butyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, dioxane and other ether solvents, or it can be benzene, toluene, xylene, chlorine Aromatic solvents such as benzene, fluorobenzene, bromobenzene, and chloronaphthalene, or alkane solvents such as chloroform, dichloromethane, dichloroethane, trichloroethane, dibromoethane, dodecane, hexadecane, etc.
  • the acid 2 can be an inorganic acid such as hydrochloric acid, sulfuric acid, phosphoric acid, or an organic acid such as acetic acid, trifluoroacetic acid, trifluoromethanesulfonic acid, p-toluenesulfonic acid, and pyridine p-toluenesulfonate.
  • the solvent 4 may be ethers such as ether, methyl isopropyl ether, diisopropyl ether, butyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, dioxane, etc.
  • the solvent may be aromatic hydrocarbon solvents such as benzene, toluene, xylene, chlorobenzene, fluorobenzene, bromobenzene, chloronaphthalene, or it may be chloroform, methylene chloride, dichloroethane, trichloroethane, dibromoethane Alkane, dodecane, hexadecane and other alkane solvents, or acetic anhydride, trifluoromethanesulfonic anhydride, trifluoroacetic anhydride and other acid anhydride solvents, considering the four solvents, specifically dioxane or toluene or Dichloroethane or acetic anhydride; the additive 2 can be oxygen, benzoquinone, tetrachlorobenzoquinone, dichlorodicyanobenzoquinone DDQ, trichlorourea cyanide, bromine, iodine, bromosuccin
  • Alkane solvents such as methyl chloride, dichloroethane, trichloroethane, dibromoethane, dodecane, hexadecane, etc., considering the three solvents, specifically it can be ethylene glycol dimethyl ether or benzene or tetrachloride
  • the molar ratio of the compound 2,8-dibromo-5,12-epoxy-5,5a,6,11,11a,12-hexahydrotetracene and acid 2 is 1:(0.01 ⁇ 100 ), specifically 1:25 or 1:0.5; the compound 2,8-dibromo-5,12-epoxy-5,5a,6,11,11a,12-hexahydrotetracene and additive 2
  • the molar ratio of is 1:(0.01-100), specifically it can be 1:0.5 or 1:2; the heating reflux and post-treatment are as described in step 1).
  • the compound of the present invention can also be mixed with a polymer, and it is even possible to be covalently bound to the molecular backbone of the polymer.
  • a polymer for example, using reactive leaving groups (for example, fluorine, chlorine, bromine, iodine, boric acid, borate, stannane, silicon ester, silane, etc.) or reactive polymerizable groups (for example, alkene, alkyne, etc.) Hydrocarbon, propylene oxide, oxetane and other groups) are particularly feasible methods to replace these compounds. Therefore, these compounds substituted by reactive groups can be used to prepare corresponding oligomers and dendrimers.
  • the oligomerization or polymerization is preferably achieved via a halogen functional group, a boric acid functional group, a tin-based functional group or a silicon-based functional group, or via a reactive polymerizable group.
  • crosslinking of the polymer can also be achieved via these reactive groups.
  • Solvents and reagents can be purchased from commercial sources, for example, chemical reagent companies such as Sinopharm, J&K, Acros, Innochem, Alfa-aesar, Adamas-beta.
  • chemical reagent companies such as Sinopharm, J&K, Acros, Innochem, Alfa-aesar, Adamas-beta.
  • the corresponding literature source and CAS number are also reported as appropriate in each case.
  • the bright red transparent liquid is high-purity 6-bromo-1,4-epoxy-1 ,4-Dihydronaphthalene.
  • the organic solvent was removed under reduced pressure to obtain a brown-red liquid.
  • the crude product is purified by 200-400 mesh silica gel column chromatography (the eluent is petroleum ether and dichloromethane), and finally a reddish brown liquid product (59 g, yield 80%) can be obtained.
  • the reddish-brown liquid is high-purity 2,8-dibromo-5,12-epoxy -5,5a,6,11,11a,12-hexahydrotetracene.
  • the purification method in this embodiment uses an electric tube furnace of Bruke Company, equipped with a quartz tube that can be evacuated and filled with gas.
  • the electric tube furnace is divided into evaporation section A and deposition section B.
  • the purification and sublimation operation is as follows: first the system pressure is pumped by a mechanical pump to 1x10 -1 pa, and then pumped to 1x10 -3 pa by a molecular pump, and then heated and purified.
  • the evaporation section is heated by resistance wire, and the temperature control is completed by the tube furnace's own system.
  • the compounds prepared in the foregoing Examples 2 and 3 were placed in a quartz boat and placed in the evaporation area, heated at 350° C. for 4 days, and deposited on B naturally.
  • the material obtained by sublimation deposition in B is the required material.
  • the furnace temperature drops below 50°C, turn off the pump, then vent the air and scrape off the required materials.
  • the source and drain of the source and drain electrodes are both composed of gold electrodes, and the thickness of the thin film device electrodes is about 20 nm. Operate in a vapor deposition machine, place the compound purified in Example 3 above in a quartz boat, heat it with 1.3 ampere current, and vaporize 50 nm at a rate of 0.1 A/S.
  • the substrate is a 300nm-thick silicon dioxide sheet modified by hexamethyltrichlorosilane. After taking it out, a different specification mask is used.
  • the gold is also evaporated in an evaporation machine, and 20-25nm is evaporated at a rate of 0.1A/s. .
  • the electrical test method is: at room temperature in the atmospheric environment, the widely used OFET test method (electrode vapor deposition or sticking to the organic layer, test on the probe station.
  • the source pin and the missing pin Poke on the gold electrode respectively, and then poke the gate pin on the bottom gate (copper sheet), keep the source gate voltage unchanged, change the source and drain voltage to test and observe the current) on the Micromanipulator 6150 manual probe station Use Keithley 4200SCS semiconductor electrical test system for testing.
  • the device structure is shown in Figure 2.
  • the source and drain electrodes are gold electrodes with a thickness of 20-25 nm
  • the organic semiconductor layer is the compound purified in Example 4
  • the insulating layer is a silicon dioxide layer modified with hexamethyltrichlorosilane (ots)
  • the gate is silicon.
  • the channel length in the following table is the channel length of the copper mesh.
  • the average value in the above table is the average value obtained by preparing 20 devices and measuring under the same conditions.
  • This example also tested the ultraviolet fluorescence spectra of the following compounds.
  • the test process was as follows: Dissolve 1 mg of the test compound in a tetrahydrofuran solution, and filter the residue with a filter due to the extremely poor solubility of the compound, and then the ultraviolet-visible spectrum and the fluorescence spectrum were respectively It was carried out on Hitachi U-3010 ultraviolet-visible spectrometer and J ⁇ S.CO FP-6600 spectrofluorometer. The operation is normal operation.
  • the test result is shown in Figure 9. It can be seen from Figure 9 that the band gaps of the thiophene and furan benzene derivatives of naphthacene are both around 2 eV, which is a narrow band gap material, which is prone to high mobility materials.
  • the source and drain electrodes are all composed of gold electrodes, and single crystals are prepared by physical vapor deposition.
  • the test is carried out.
  • the test method is to pierce the needle on the electrode and at the same time pierce the grid needle on the bottom grid electrode.
  • the gate uses a copper sheet
  • the gate uses a copper sheet
  • the gate voltage unchanged (the voltage between the source and the gate, the source is 0V)
  • the test is performed by changing the source and drain voltage.
  • the device uses bottom-gate top contact (gate at the bottom, top source and drain), and its structure is shown in Figure 2.
  • the source and drain electrodes are 25nm thick gold electrodes
  • the organic semiconductor layer is the compound purified in Example 4 above
  • the insulating layer is A silicon dioxide layer modified by hexamethyltrichlorosilane (ots)
  • the gate is silicon.
  • the average value in the above table is the average value obtained by preparing 20 devices and measuring under the same conditions.
  • an atomic force scanning microscope was used to test the tetracene derivative (DPT) thin film device shown in formula 2.
  • the result is shown in FIG. 12, which shows that the thin film is regular and large. Lump-shaped crystals reduce the grain boundaries, and the mobility of the device should be higher.
  • This example also tested the UV Photoelectron Spectroscopy (UPS) of the benzene derivative of naphthacene shown in Formula 2, and the result is shown in FIG. 14. From FIG. 14, the HOMO and LUMO can be known, so that the band gap can be calculated. After calculation, it is similar to the band gap calculated by ultraviolet, and it is expected to be a narrow band gap material.
  • UPS UV Photoelectron Spectroscopy
  • the stability data of the continuous operation of the tetracene benzene derivative single crystal transistor device shown in formula 2 (silicon and silicon dioxide are used as the gate and insulating layer, and gold is used as the source and drain electrodes.
  • the device does not undergo any special protection and packaging. Processing, atmospheric test conditions, test voltage range: grid voltage 20V--40V, source-drain voltage: -40V; test step: 2V) as shown in Figure 21. It can be seen from Figure 21 that the electronic device constructed based on this molecule has excellent working stability. During the continuous tracking test for 40 hours, the performance orientation of the device is basically the same, and with the extension of the test time, the curve of the device shows More standard, showing its excellent optoelectronic working characteristics.
  • FIG. 25 The bright field (left) and fluorescence (right) photographs of the benzene derivative of naphthacene shown in formula 2 doped (doping amount is 1-10%) in PMMA are shown in FIG. 25.
  • the figure shows that this type of material has obvious luminescence characteristics and can be used in the application research of electroluminescent devices, biosensing devices, photonics devices and related functional devices.
  • FIG. 26 The bright field (left one) of the single crystal of the benzene derivative of naphthacene shown in Formula 2 and the fluorescence photos at different excitation wavelengths are shown in FIG. 26.
  • the figure shows that this type of material also has good luminescence properties in the single crystal state, which is better than the traditional fused-ring acene material system, indicating its potential important applications in organic micro-nano electro-optical devices and biosensing.
  • the electrical performance test data of the benzene derivative photoelectric device of naphthacene shown in Formula 2 is shown in FIG. 27. It can be seen from Fig. 27 that under the condition of applying light, the photocurrent increases with the increase of the irradiated light intensity, showing an excellent photoresponse. Without optimization of the system device structure and interface conditions, the best light sensitivity (P) of the obtained device can be as high as 10 6 ; in addition, this type of device also exhibits a certain magnetic field response characteristic, indicating that this type of compound Potential applications in multifunctional optoelectronic devices and organic spin.
  • P light sensitivity

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Abstract

L'invention concerne un dérivé de tétracène 2,8-disubstitué représenté par la formule I, son procédé de préparation et son utilisation pharmaceutique. Le composé peut être utilisé pour préparer un dispositif semi-conducteur organique, en particulier un transistor à effet de champ organique (OFET). Un monocristal et un dispositif à couche mince, tels que préparés à partir du dérivé de tétracène mentionné ci-dessus, ont une mobilité, une tension seuil et un rapport de commutation supérieurs. Le procédé de préparation est simple, peut augmenter de manière considérable le rendement de 2,8-dibromotétracène, réduit le nombre d'étapes de post-traitement d'intermédiaires, augmente l'efficacité de synthèse, réduit le temps de préparation, et a un coût relativement bas. Le rendement total de la voie de synthèse atteint approximativement 50 %. La présente invention est très appropriée pour la préparation à l'échelle dans un laboratoire, et peut fournir des matières premières suffisantes pour la préparation d'un dispositif photoélectronique contenant le dérivé de tétracène.
PCT/CN2020/123012 2019-10-22 2020-10-22 Dérivé de tétracène, son procédé de préparation et son utilisation WO2021078217A1 (fr)

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CN113999240B (zh) * 2021-11-03 2023-09-05 复旦大学 一类含有杂原子的共轭稠环大环材料及其制备方法和应用

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