WO2023013273A1 - 縮合環化合物、半導体材料および電子デバイス - Google Patents

縮合環化合物、半導体材料および電子デバイス Download PDF

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WO2023013273A1
WO2023013273A1 PCT/JP2022/024968 JP2022024968W WO2023013273A1 WO 2023013273 A1 WO2023013273 A1 WO 2023013273A1 JP 2022024968 W JP2022024968 W JP 2022024968W WO 2023013273 A1 WO2023013273 A1 WO 2023013273A1
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condensed ring
compound
formula
ring compound
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French (fr)
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達人 安藤
敬祐 林
伸行 松澤
宏行 前嶋
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Panasonic Intellectual Property Management Co Ltd
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Priority to CN202280052583.5A priority patent/CN117794888A/zh
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • 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
    • H10K85/625—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing at least one aromatic ring having 7 or more carbon atoms, e.g. azulene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/20—Polycyclic condensed hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10D—INORGANIC ELECTRIC SEMICONDUCTOR DEVICES
    • H10D30/00—Field-effect transistors [FET]
    • H10D30/60—Insulated-gate field-effect transistors [IGFET]
    • H10D30/67—Thin-film transistors [TFT]
    • 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
    • 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]
    • H10K10/484—Insulated gate field-effect transistors [IGFETs] characterised by the channel regions
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • 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
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/54—Ortho- or ortho- and peri-condensed systems containing more than five condensed rings
    • 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]

Definitions

  • the present disclosure relates to fused ring compounds, semiconductor materials and electronic devices.
  • Electronic devices include, for example, thin film transistors (TFTs).
  • TFTs thin film transistors
  • a semiconductor film may be referred to as a semiconductor layer.
  • Various advantages are obtained by using an organic material for the semiconductor layer.
  • a conventional inorganic thin film transistor using an inorganic material such as inorganic amorphous silicon as a base requires a heating process at a temperature of about 350° C. to 400° C. during fabrication.
  • an organic TFT can be manufactured by a heating process at a low temperature of about 50.degree. C. to 200.degree.
  • the organic TFT it is possible to fabricate the element on a base such as a plastic film having low heat resistance. Furthermore, when an organic material is used, there is an advantage that a semiconductor layer can be formed using a simple method such as a spin coating method, an inkjet method, or a printing method. These methods allow the fabrication of large area devices at low cost.
  • Patent Documents 1 to 4 focus on research on organic materials for forming organic semiconductor layers.
  • Patent Documents 1 to 3 disclose condensed thiophene molecules having a structure in which two thiophene rings and 2 to 7 other monocyclic aromatic rings are condensed.
  • Patent Document 4 discloses a condensed thiophene molecule having a structure in which four thiophene rings and four to nine other monocyclic aromatic rings are condensed.
  • Organic semiconductors and organic semiconductor films with good properties can improve the performance of electronic devices. Therefore, research is needed to further improve the properties of organic semiconductors and organic semiconductor films.
  • Condensed thiophene molecules that function as p-type organic semiconductor materials include benzothieno-benzothiophene (BTBT) and dinaphthothienothiophene (DNTT). These ring-fused thiophene molecules are known as materials exhibiting relatively high carrier mobility.
  • New condensed ring compounds suitable for semiconductor materials are in demand.
  • the condensed ring compound in one aspect of the present disclosure is having a fused ring comprising multiple monocyclic aromatic rings;
  • the number of the monocyclic aromatic rings is 11, Among the 11 monocyclic aromatic rings, the number of thiophene rings is 2 or less,
  • the fused ring includes two naphthacene structures.
  • the present disclosure provides new condensed ring compounds suitable for semiconductor materials.
  • FIG. 1 is a structural schematic diagram showing an example of an electronic device using the fused ring compound of the present disclosure.
  • FIG. 2 is a structural schematic diagram showing another example of an electronic device using the fused ring compound of the present disclosure.
  • the carrier mobility of conventional fused-ring thiophene molecules cannot be said to be sufficiently high. Therefore, it is difficult to obtain electronic devices with sufficiently high operating speed using conventional fused-ring thiophene molecules.
  • the hole mobility of fused ring thiophene molecules such as BTBT and DNTT is about 5 to 10 cm 2 /Vs at most.
  • an operation speed of only about 1 MHz can be obtained in a device having a gate length of 10 ⁇ m.
  • the gate length of about 1 ⁇ m corresponds to the lower limit of the gate length achievable using the coating method. Therefore, in the field of RF-ID (Radio Frequency Identification), which requires an operating speed of about 100 MHz, an organic semiconductor material with higher carrier mobility is desired.
  • RF-ID Radio Frequency Identification
  • Reorientation energy is known as a physical quantity that greatly contributes to carrier mobility.
  • the reorientation energy is a physical quantity that depends on the element arrangement of a single molecule and the three-dimensional shape of the single molecule. Specifically, the reorientation energy represents the amount of change in energy accompanying structural deformation of molecules when carriers are hopping-conducted between a plurality of molecules. The lower the reorientation energy, the better the carrier mobility of the semiconductor material tends to be.
  • Semiconductor materials with enhanced carrier mobility enable electronic devices with high operating speeds.
  • the fused ring compound according to the first aspect of the present disclosure is having a fused ring comprising multiple monocyclic aromatic rings; In the condensed ring, the number of the monocyclic aromatic rings is 11, Among the 11 monocyclic aromatic rings, the number of thiophene rings is 2 or less, The fused ring includes two naphthacene structures.
  • the condensed ring compound tends to have sufficiently low reorientation energy and high carrier mobility. It can be said that this condensed ring compound is suitable for a semiconductor material.
  • the eleven monocyclic aromatic rings may each independently be a benzene ring or a thiophene ring.
  • the condensed ring may have a linear structure.
  • the condensed ring compound according to any one of the first to third aspects may be represented by the following formula (I).
  • R A1 to R A18 are each independently a hydrogen atom or a hydrocarbon group
  • Ar A1 and Ar A2 are each independently a benzene optionally having a substituent. It is a ring or a thiophene ring optionally having a substituent.
  • the fused ring compound according to any one of the first to fourth aspects is represented by the following formula (I-1), the following formula (I-2), the following formula (I-3 ), the following formula (I-4) or the following formula (I-5).
  • R a1 to R a26 each independently represent a hydrogen atom or a hydrocarbon group.
  • R b1 to R b22 are each independently a hydrogen atom or a hydrocarbon group.
  • R c1 to R c22 are each independently a hydrogen atom or a hydrocarbon group.
  • R d1 to R d24 are each independently a hydrogen atom or a hydrocarbon group.
  • R e1 to R e24 are each independently a hydrogen atom or a hydrocarbon group.
  • the condensed ring compounds according to the second to fifth aspects are suitable for semiconductor materials.
  • the condensed ring may have C2V symmetry.
  • the condensed ring compound according to the sixth aspect tends to be easily synthesized.
  • the semiconductor material according to the seventh aspect of the present disclosure is A fused ring compound according to any one of the first to sixth aspects is included.
  • the carrier mobility of the semiconductor material tends to be large.
  • An electronic device includes A semiconductor material according to the seventh aspect is included.
  • the operating speed of the electronic device tends to be high.
  • the electronic device includes a source electrode; a drain electrode; a gate electrode; a semiconductor film containing the semiconductor material according to the seventh aspect; Prepare.
  • the operating speed of the electronic device tends to be high.
  • the condensed ring compound C of this embodiment has a condensed ring F containing a plurality of monocyclic aromatic rings M.
  • the number of monocyclic aromatic rings M is 11.
  • the number of thiophene rings is 2 or less.
  • the fused ring F contains two naphthacene structures.
  • the monocyclic aromatic ring M means one ring structure having aromaticity.
  • monocyclic aromatic ring M may be simply referred to as "aromatic ring M.”
  • the aromatic ring M typically contains carbon atoms.
  • the aromatic ring M may be composed only of carbon atoms, or may contain heteroatoms such as sulfur atoms together with the carbon atoms.
  • the number of carbon atoms in the aromatic ring M is not particularly limited, and is 4 or more and 10 or less.
  • Specific examples of the aromatic ring M include a benzene ring and a thiophene ring.
  • 11 aromatic rings M may each independently be a benzene ring or a thiophene ring.
  • the condensed ring F may be composed of 11 benzene rings, may be composed of 1 thiophene ring and 10 benzene rings, or may be composed of 2 thiophene rings and 9 benzene rings. may have been
  • the condensed ring compound C since the number of thiophene rings contained in the condensed ring F is 2 or less, the condensed ring compound C tends to have sufficiently high carrier mobility. Furthermore, the number of thiophene rings contained in the condensed ring F is 2 or less, and the number of aromatic rings M constituting the condensed ring F is 11, so that the condensed ring compound C has sufficiently high carrier mobility. tend to have As described below, the condensed ring compound C can typically be used as a p-type semiconductor material. Therefore, in the present disclosure, the carrier mobility of the condensed ring compound C is sometimes referred to as the hole mobility.
  • the aromatic rings M are condensed.
  • "the aromatic rings M are fused” means that two adjacent aromatic rings M share two carbon atoms and a covalent bond formed between these carbon atoms. means that
  • the condensed ring F has, for example, a linear structure.
  • the condensed ring F has a linear structure means that in the condensed ring F, 11 aromatic rings M are arranged in a single line without branching. That is, each of all the aromatic rings M constituting the condensed ring F is condensed with only one or two adjacent aromatic rings M.
  • a condensed ring F having a linear structure does not have an aromatic ring M condensed with three or more adjacent aromatic rings M. If there is even one aromatic ring M condensed with three or more adjacent aromatic rings M, the condensed ring F does not have a linear structure but has a branched structure. can be assumed to exist.
  • the 11 aromatic rings M may not be arranged linearly.
  • the condensed ring F may have a bent structure.
  • "the condensed ring F has a bent structure” means that in the condensed ring F, some of the aromatic rings M are arranged so as to be bent.
  • each of the two terminal aromatic rings M is condensed with only one adjacent aromatic ring M.
  • the two aromatic rings M present at the ends may each independently be a benzene ring or a thiophene ring.
  • the aromatic ring M present at the terminal is a thiophene ring
  • the thiophene ring is fused with one adjacent aromatic ring M so as to share the carbon atom at the 2nd position and the carbon atom at the 3rd position.
  • the 1-position atom in the thiophene ring is a sulfur atom.
  • each of the aromatic rings M other than the two terminal aromatic rings M is condensed with the adjacent two aromatic rings M.
  • the other aromatic ring M is a benzene ring
  • the benzene ring is condensed with one adjacent aromatic ring M so as to share the carbon atom at the 1-position and the carbon atom at the 2-position
  • It may be condensed with the other adjacent aromatic ring M, or may be condensed with the other adjacent aromatic ring M so as to share the 5-position carbon atom and the 6-position carbon atom.
  • the fused ring F includes two naphthacene structures.
  • the naphthacene structure is represented by the following formula (1).
  • the benzene rings forming the naphthacene structures do not overlap each other.
  • the condensed ring compound C tends to have sufficiently high carrier mobility because the condensed ring F has two naphthacene structures.
  • the condensed ring F may or may not have symmetry. From the viewpoint that the condensed ring compound C can be easily synthesized, the production cost can be reduced, and the hole mobility of the condensed ring compound C can be further improved, the condensed ring F may have C2V symmetry. . "The condensed ring F has C2V symmetry" means that the condensed ring F has a two-fold rotational symmetry axis and a mirror plane parallel to the rotational symmetry axis. In this disclosure, the axis of rotational symmetry is sometimes referred to as the principal axis of the condensed ring F. Examples of the condensed ring F having C2V symmetry include structures represented by the following formula (2). In equation (2), the dashed line indicates the axis of rotational symmetry. At the position of the axis of rotational symmetry, the mirror plane extends in the direction perpendicular to the plane of the paper.
  • the condensed ring F is connected to a hydrogen atom or a substituent.
  • Substituents connected to condensed ring F are not particularly limited.
  • the substituents for example, do not contain heteroatoms.
  • a specific example of a substituent is a hydrocarbon group.
  • the number of carbon atoms in the hydrocarbon group is not particularly limited, and is, for example, 1 or more and 20 or less.
  • the hydrocarbon group may be linear, branched, or cyclic. Examples of hydrocarbon groups include alkyl groups and aryl groups.
  • the number of carbon atoms in the alkyl group may be 1 or more and 20 or less, 1 or more and 10 or less, or 3 or more and 8 or less.
  • Alkyl groups include methyl group, ethyl group (Et), n-propyl group, isopropyl group, n-butyl group, isobutyl group (i-Bi), sec-butyl group, tert-butyl group, pentyl group and hexyl group. , heptyl group, octyl group, nonyl group, and decyl group.
  • the number of carbon atoms in the aryl group may be 6 or more and 18 or less, or may be 6 or more and 12 or less.
  • the aryl group includes a phenyl group (Ph), naphthyl group, 4-biphenyl group, 3-biphenyl group, 2-biphenyl group and the like.
  • the condensed ring compound C is represented, for example, by the following formula (I).
  • the condensed ring compound C represented by formula (I) tends to have a smaller reorientation energy than the condensed ring compound C represented by formula (II) described below.
  • R A1 to R A18 are each independently a hydrogen atom or a hydrocarbon group.
  • Hydrocarbon groups include those described above.
  • Ar A1 and Ar A2 are each independently an optionally substituted benzene ring or an optionally substituted thiophene ring.
  • substituents on the benzene ring and thiophene ring are hydrocarbon groups. Hydrocarbon groups include those described above.
  • the condensed ring compound C may be represented by the following formula (I-1).
  • R a1 to R a26 are each independently a hydrogen atom or a hydrocarbon group. Hydrocarbon groups include those described above.
  • the condensed ring compound C represented by formula (I-1) is a condensed polycyclic hydrocarbon with a condensed ring F having a linear structure. In this condensed ring compound C, the condensed ring F has C2V symmetry.
  • R a1 to R a26 is an alkyl group or an aryl group, good too.
  • R a1 to R a26 may each independently be a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 18 carbon atoms.
  • Alkyl groups and aryl groups include those described above. Specific examples of combinations of R a1 to R a26 in formula (I-1) are shown in Table 1 below. In Table 1, the compound entry shows abbreviations of condensed ring compounds C having specific R a1 to R a26 .
  • the condensed ring compound C may be represented by the following formula (I-2).
  • R b1 to R b22 are each independently a hydrogen atom or a hydrocarbon group. Hydrocarbon groups include those described above.
  • the fused ring compound C represented by formula (I-2) is a fused ring thiophene molecule with a fused ring F having a linear structure. In this condensed ring compound C, the condensed ring F has C2V symmetry.
  • R b1 to R b22 is an alkyl group or an aryl group, good too.
  • R b1 to R b22 may each independently be a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 18 carbon atoms.
  • Alkyl groups and aryl groups include those described above. Specific examples of combinations of R b1 to R b22 in formula (I-2) are shown in Table 2 below. In Table 2, the compound entry shows abbreviations of condensed ring compounds C having specific R b1 to R b22 .
  • the condensed ring compound C may be represented by the following formula (I-3).
  • R c1 to R c22 are each independently a hydrogen atom or a hydrocarbon group. Hydrocarbon groups include those described above.
  • the fused ring compound C represented by formula (I-3) is a fused ring thiophene molecule with a fused ring F having a linear structure. In this condensed ring compound C, the condensed ring F has C2V symmetry.
  • At least one selected from R c1 to R c22 is an alkyl group or an aryl group, may be an alkyl group.
  • R c1 to R c22 may each independently be a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 18 carbon atoms.
  • Alkyl groups and aryl groups include those described above. Specific examples of combinations of R c1 to R c22 in formula (I-3) are shown in Table 3 below. In Table 3, the compound entry shows abbreviations of condensed ring compounds C having specific R c1 to R c22 .
  • the condensed ring compound C may be represented by the following formula (I-4).
  • R d1 to R d24 are each independently a hydrogen atom or a hydrocarbon group. Hydrocarbon groups include those described above.
  • the fused ring compound C represented by formula (I-4) is a fused ring thiophene molecule with a fused ring F having a linear structure. In this condensed ring compound C, the condensed ring F does not have symmetry.
  • At least one selected from R d1 to R d24 is an alkyl group or an aryl group, may be an alkyl group.
  • R d1 to R d24 may each independently be a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 18 carbon atoms.
  • Alkyl groups and aryl groups include those described above. Specific examples of combinations of R d1 to R d24 in formula (I-4) are shown in Table 4 below. In Table 4, the compound entry shows the abbreviations of the condensed ring compounds C having specific Rd1 to Rd24 .
  • the condensed ring compound C may be represented by the following formula (I-5).
  • R e1 to R e24 are each independently a hydrogen atom or a hydrocarbon group. Hydrocarbon groups include those described above.
  • the fused ring compound C represented by formula (I-5) is a fused ring thiophene molecule with a fused ring F having a linear structure. In this condensed ring compound C, the condensed ring F does not have symmetry.
  • At least one selected from R e1 to R e24 is an alkyl group or an aryl group, may be an alkyl group.
  • R e1 to R e24 may each independently be a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 18 carbon atoms.
  • Alkyl groups and aryl groups include those described above. Specific examples of combinations of R e1 to R e24 in formula (I-5) are shown in Table 5 below. In Table 5, the compound entry shows abbreviations of condensed ring compounds C having specific R e1 to R e24 .
  • the fused ring compound C may be represented by formula (I-1), formula (I-2), formula (I-3), formula (I-4) or formula (I-5), and formula (I -1), formula (I-2) or formula (I-3).
  • the condensed ring compound C represented by formula (I-1), formula (I-2) or formula (I-3) has a highly symmetrical condensed ring F and tends to be easily synthesized.
  • the condensed ring compound C may be represented by the following formula (II).
  • R B1 to R B18 are each independently a hydrogen atom or a hydrocarbon group. Hydrocarbon groups include those described above.
  • Ar B1 and Ar B2 are each independently an optionally substituted benzene ring or an optionally substituted thiophene ring.
  • substituents on the benzene ring and thiophene ring are hydrocarbon groups. Hydrocarbon groups include those described above.
  • the condensed ring compound C may be represented by the following formula (II-1).
  • R f1 to R f26 are each independently a hydrogen atom or a hydrocarbon group. Hydrocarbon groups include those described above.
  • the condensed ring compound C represented by formula (II-1) is a condensed polycyclic hydrocarbon with a condensed ring F having a linear structure. In this condensed ring compound C, the condensed ring F has C2V symmetry.
  • R f1 to R f26 is an alkyl group or an aryl group, good too.
  • R f1 to R f26 may each independently be a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 18 carbon atoms.
  • Alkyl groups and aryl groups include those described above. Specific examples of combinations of R f1 to R f26 in formula (II-1) are shown in Table 6 below. In Table 6, the compound entry shows abbreviations of condensed ring compounds C having specific R f1 to R f26 .
  • the condensed ring compound C may be represented by the following formula (II-2).
  • R g1 to R g22 are each independently a hydrogen atom or a hydrocarbon group. Hydrocarbon groups include those described above.
  • the fused ring compound C represented by formula (II-2) is a fused ring thiophene molecule with a fused ring F having a linear structure. In this condensed ring compound C, the condensed ring F has C2V symmetry.
  • R g1 to R g22 is an alkyl group or an aryl group, good too.
  • R g1 to R g22 may each independently be a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 18 carbon atoms.
  • Alkyl groups and aryl groups include those described above. Specific examples of combinations of R g1 to R g22 in formula (II-2) are shown in Table 7 below. In Table 7, the compound entry shows abbreviations of fused ring compounds C having specific R g1 to R g22 .
  • the condensed ring compound C may be represented by the following formula (II-3).
  • R h1 to R h22 are each independently a hydrogen atom or a hydrocarbon group. Hydrocarbon groups include those described above.
  • the fused ring compound C represented by formula (II-3) is a fused ring thiophene molecule with a fused ring F having a linear structure. In this condensed ring compound C, the condensed ring F has C2V symmetry.
  • At least one selected from R h1 to R h22 is an alkyl group or an aryl group, may be an alkyl group.
  • R h1 to R h22 may each independently be a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 18 carbon atoms.
  • Alkyl groups and aryl groups include those described above. Specific examples of combinations of R h1 to R h22 in formula (II-3) are shown in Table 8 below. In Table 8, the compound entry shows abbreviations for fused ring compounds C having specific R h1 to R h22 .
  • the condensed ring compound C may be represented by the following formula (II-4).
  • R i1 to R i24 are each independently a hydrogen atom or a hydrocarbon group. Hydrocarbon groups include those described above.
  • the fused ring compound C represented by formula (II-4) is a fused ring thiophene molecule with a fused ring F having a linear structure. In this condensed ring compound C, the condensed ring F does not have symmetry.
  • At least one selected from R i1 to R i24 is an alkyl group or an aryl group, may be an alkyl group.
  • R i1 to R i24 may each independently be a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 18 carbon atoms.
  • Alkyl groups and aryl groups include those described above. Specific examples of combinations of R i1 to R i24 in formula (II-4) are shown in Table 9 below. In Table 9, the compound entry shows abbreviations of condensed ring compounds C having specific R i1 to R i24 .
  • the condensed ring compound C may be represented by the following formula (II-5).
  • R j1 to R j24 are each independently a hydrogen atom or a hydrocarbon group. Hydrocarbon groups include those described above.
  • the fused ring compound C represented by formula (II-5) is a fused ring thiophene molecule with a fused ring F having a linear structure. In this condensed ring compound C, the condensed ring F does not have symmetry.
  • At least one selected from R j1 to R j24 is an alkyl group or an aryl group, may be an alkyl group.
  • R j1 to R j24 may each independently be a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 18 carbon atoms.
  • Alkyl groups and aryl groups include those described above. Specific examples of combinations of R j1 to R j24 in formula (II-5) are shown in Table 10 below. In Table 10, the compound entry shows abbreviations of condensed ring compounds C having specific R j1 to R j24 .
  • the condensed ring compound C can be synthesized by using a commercially available compound as a starting material and performing a combination of known reactions such as a halogenation reaction and a Sonogashira coupling reaction. If by-products are produced by the reaction, they may be separated and purified by known methods such as column chromatography.
  • Fused ring compound C of the present disclosure can be identified by elemental analysis, mass spectrometry and 13 C-NMR. That is, the ratio of the number of atoms constituting one molecule of the condensed ring compound C is specified by elemental analysis. The molecular weight of the condensed ring compound C is determined by mass spectrometry. Based on these results, the molecular formula of the condensed ring compound C can be determined. Furthermore, the structural formula of the condensed ring compound C can be determined by analyzing the amount of chemical shift of each peak obtained by 13 C-NMR. These methods can also specify the type of substituent and the position of the substituent.
  • the condensed ring compound C of the present embodiment tends to have sufficiently low reorientation energy and high carrier mobility.
  • the reorientation energy due to the movement of holes is not particularly limited, and is, for example, 0.10 eV or less, may be 0.08 eV or less, may be 0.07 eV or less, or may be 0 It may be .06 eV or less.
  • the lower limit of the reorientation energy of the condensed ring compound C is not particularly limited, and is, for example, 0.04 eV.
  • charge hopping rate corresponding to the carrier mobility can be calculated by the following formula (F1).
  • Formula (F1) is reported in David R. Evans et al, Organic Electronics, 2016, Vol. 29, p. 50. and others.
  • ⁇ is the charge hopping rate.
  • ⁇ G is the amount of change in free energy associated with charge transfer.
  • ⁇ is the reorientation energy in Marcus theory.
  • H is the electron coupling between molecules.
  • k B is the Boltzmann constant.
  • T is temperature.
  • h- (h-bar) is Planck's constant.
  • the reorientation energy is a physical quantity that depends on the element arrangement of the single molecule and the three-dimensional shape of the single molecule. Specifically, the reorientation energy represents the amount of change in energy accompanying structural deformation of molecules when carriers are hopping-conducted between a plurality of molecules. The reorientation energy greatly contributes to the charge transport speed, and the smaller the value, the more the carrier mobility tends to improve. A good correlation between reorientation energy and carrier mobility is reported in Shigeyoshi Sakaki et al, J. Phys. Chem. A, 1999, Vol. 103, p. 5551-5556.
  • the reorientation energy ⁇ is the energy of four points: E (neutral state in neutral geometry), E * (neutral state in ionic geometry), E ⁇ (ionic state in ionic geometry) and E ⁇ * (ionic state in neutral geometry) is defined by the following formula (F2) using the value of
  • the reorientation energy ⁇ can be calculated, for example, by density functional theory.
  • Known software such as Gaussian09 can be used for this calculation.
  • B3LYP can be used as the functional.
  • 6-31G(d,p) can be used as a basis function.
  • the condensed ring compound C of the present disclosure tends to have excellent carrier mobility. Therefore, the condensed ring compound C is suitable for semiconductor materials.
  • the present disclosure provides a semiconductor material S containing a condensed ring compound C from another aspect thereof.
  • the fused ring compound C has, for example, excellent hole mobility.
  • a semiconductor material S containing such a condensed ring compound C can be used, for example, as a p-type semiconductor material.
  • the semiconductor material S containing the condensed ring compound C is sometimes referred to as a molecular organic semiconductor material or a carbon-based hole transport material.
  • the semiconductor material S containing the fused ring compound C of the present disclosure can be used for electronic devices.
  • the present disclosure provides, from another aspect thereof, an electronic device including a semiconductor material S.
  • the electronic device in particular comprises a semiconductor film comprising a semiconductor material S.
  • an electronic device may be referred to as an electronic element.
  • the frequency characteristics of the electronic device can be improved.
  • a specific example of the electronic device is a transistor.
  • FIG. 1 is a structural schematic diagram showing an example of an electronic device using the fused ring compound C of the present disclosure.
  • the electronic device 10 includes a gate electrode 1, a source electrode 3, a drain electrode 4 and a semiconductor film 5.
  • the electronic device 10 may further include a gate insulating film 2 .
  • the semiconductor film 5 contains a semiconductor material S.
  • FIG. Electronic device 10 in FIG. 1 is typically a transistor. Specifically, FIG. 1 shows the basic structure of a transistor.
  • the gate electrode 1 is plate-shaped, for example, and supports the gate insulating film 2 , the source electrode 3 , the drain electrode 4 and the semiconductor film 5 .
  • Gate insulating film 2 is located on gate electrode 1 and covers the main surface of gate electrode 1 .
  • Gate insulating film 2 may cover the entire main surface of gate electrode 1 .
  • Each of the source electrode 3 and the drain electrode 4 is strip-shaped, for example.
  • the source electrode 3 and the drain electrode 4 are positioned on the gate insulating film 2 so as not to contact each other.
  • a space is formed between the source electrode 3 and the drain electrode 4 .
  • Each of source electrode 3 and drain electrode 4 is in contact with gate insulating film 2 .
  • Source electrode 3 and drain electrode 4 each extend from one of a pair of end surfaces of gate electrode 1 to the other.
  • the semiconductor film 5 is in contact with each of the gate insulating film 2, the source electrode 3 and the drain electrode 4. Specifically, the semiconductor film 5 covers the surface of the gate insulating film 2 exposed between the source electrode 3 and the drain electrode 4 and also covers the source electrode 3 and the drain electrode 4 respectively. The semiconductor film 5 fills the space existing between the source electrode 3 and the drain electrode 4 .
  • the material of the gate electrode 1 is not particularly limited as long as it is used as an electrode material in the field of electronic devices.
  • the material of the gate electrode 1 is, for example, metal.
  • Materials for the gate electrode 1 include silicon, gold, copper, nickel, and aluminum.
  • the material of the gate insulating film 2 is not particularly limited as long as it has electrical insulation.
  • Materials for the gate insulating film 2 include metal oxides, metal nitrides, polymer materials, and the like.
  • metal oxides include silicon oxides such as SiO2 , tantalum oxides such as Ta2O5, aluminum oxides such as Al2O3, titanium oxides such as TiO2 , and yttrium oxides such as Y2O3 . and lanthanum oxides such as La 2 O 3 .
  • Metal nitrides include silicon nitrides such as Si 3 N 4 .
  • Polymer materials include epoxy resins, polyimide (PI) resins, polyphenylene ether (PPE) resins, polyphenylene oxide resins (PPO), polyvinylpyrrolidone (PVP) resins, and the like.
  • Materials for the source electrode 3 and the drain electrode 4 include the materials described above for the gate electrode 1 .
  • the semiconductor film 5 contains the semiconductor material S as described above.
  • the semiconductor film 5 is a p-type semiconductor film containing the condensed ring compound C.
  • the content of the condensed ring compound C in the semiconductor film 5 is not particularly limited, and is, for example, 0.1% by mass or more, and may be 1% by mass or more. From the viewpoint of improving the hole mobility, the content of the condensed ring compound C may be 10% by mass or more, 50% by mass or more, or 100% by mass.
  • the semiconductor film 5 may further contain materials other than the condensed ring compound C.
  • Other materials include fullerene, perylene diimide, polythiophene, condensed ring thiophene molecules other than the condensed ring compound C, and the like.
  • the semiconductor film 5 can be formed by known methods such as a vacuum deposition method and a coating method.
  • a vacuum deposition method the semiconductor film 5 having a content of the condensed ring compound C of 100% by mass can be formed by using only the condensed ring compound C as the deposition material.
  • FIG. 2 is a structural schematic diagram showing another example of an electronic device using the fused ring compound C of the present disclosure.
  • the electronic device 11 includes a gate electrode 17, a source electrode 13, a drain electrode 14 and a semiconductor film 15.
  • the electronic device 11 may further include underlying substrate 12 and gate insulating film 16 .
  • the semiconductor film 15 contains the semiconductor material S.
  • FIG. Electronic device 11 in FIG. 2 is typically a transistor.
  • FIG. 2 shows another basic structure of a transistor.
  • the base substrate 12 is plate-shaped, for example, and supports the source electrode 13, the drain electrode 14, the semiconductor film 15, the gate insulating film 16 and the gate electrode 17.
  • the underlying substrate 12 has, for example, an insulating layer.
  • Underlying substrate 12 may comprise a silicon wafer and an insulating layer overlying the silicon wafer. In the underlying substrate 12, the insulating layer may cover the entire main surface of the silicon wafer.
  • Each of the source electrode 13 and the drain electrode 14 is strip-shaped, for example.
  • the source electrode 13 and the drain electrode 14 are located on the underlying substrate 12 so as not to contact each other.
  • a space is formed between the source electrode 13 and the drain electrode 14 .
  • Each of the source electrode 13 and the drain electrode 14 is in contact with the base substrate 12 , more specifically, in contact with the insulating layer of the base substrate 12 .
  • the source electrode 13 and the drain electrode 14 each extend from one of a pair of end surfaces of the underlying substrate 12 to the other.
  • the semiconductor film 15 is in contact with the underlying substrate 12, the source electrode 13 and the drain electrode 14, respectively. Specifically, the semiconductor film 15 covers the exposed surface of the base substrate 12 between the source electrode 13 and the drain electrode 14 and also covers the source electrode 13 and the drain electrode 14 . The semiconductor film 15 is in contact with the insulating layer of the underlying substrate 12 . The semiconductor film 15 fills the space existing between the source electrode 13 and the drain electrode 14 .
  • the gate insulating film 16 is located on the semiconductor film 15 and covers the main surface of the semiconductor film 15 .
  • the gate insulating film 16 may cover the entire main surface of the semiconductor film 15 .
  • the gate electrode 17 is strip-shaped, for example.
  • the gate electrode 17 is located on the gate insulating film 16 and is in contact with the gate insulating film 16 .
  • the gate electrode 17 extends from one end surface of the pair of end surfaces of the underlying substrate 12 to the other end surface.
  • the gate electrode 17 is located between the source electrode 13 and the drain electrode 14 when the electronic device 11 is viewed from above.
  • the material of the insulating layer of the underlying substrate 12 is not particularly limited as long as it has electrical insulation.
  • Materials for the insulating layer include metal oxides, metal nitrides, polymer materials, and the like.
  • metal oxides include silicon oxides such as SiO2 , tantalum oxides such as Ta2O5, aluminum oxides such as Al2O3, titanium oxides such as TiO2 , and yttrium oxides such as Y2O3 . and lanthanum oxides such as La 2 O 3 .
  • Metal nitrides include silicon nitrides such as Si 3 N 4 .
  • Polymer materials include epoxy resins, polyimide (PI) resins, polyphenylene ether (PPE) resins, polyphenylene oxide resins (PPO), polyvinylpyrrolidone (PVP) resins, and the like.
  • the material for the source electrode 13 and the drain electrode 14 is not particularly limited as long as it is used as an electrode material in the field of electronic devices.
  • the material of the source electrode 13 and the drain electrode 14 is, for example, metal.
  • Materials for the source electrode 13 and the drain electrode 14 include silicon, gold, copper, nickel, and aluminum.
  • the semiconductor film 15 contains the semiconductor material S as described above.
  • the semiconductor film 15 is a p-type semiconductor film containing the condensed ring compound C.
  • the content of the condensed ring compound C in the semiconductor film 15 is not particularly limited, and is, for example, 0.1% by mass or more, and may be 1% by mass or more. From the viewpoint of improving the hole mobility, the content of the condensed ring compound C may be 10% by mass or more, 50% by mass or more, or 100% by mass.
  • the semiconductor film 15 may further contain materials other than the condensed ring compound C.
  • Other materials include fullerene, perylene diimide, polythiophene, condensed ring thiophene molecules other than the condensed ring compound C, and the like.
  • the material of the gate insulating film 16 is not particularly limited as long as it has electrical insulation.
  • Materials for the gate insulating film 16 include the materials described above for the insulating layer of the underlying substrate 12 .
  • Materials for the gate electrode 17 include the materials described above for the source electrode 13 and the drain electrode 14 .
  • DNTT Dinaphthothienothiophene
  • compound (i-1) to compound (i-9) in Table 1 compound (ii-1) to compound (ii-3) in Table 2, compound (iii-1 in Table 3) ) to compound (iii-3), compound (iv-1) in Table 4, compound (v-1) in Table 5, compound (vi-1) in Table 6 and compound (vii-1) in Table 7,
  • DNTT is known as a p-type organic semiconductor material with high hole mobility.
  • the reorientation energy was calculated by the density functional theory based on the formula (F2) described above. Specifically, the reorientation energy was calculated using the calculation software Gaussian09. At this time, B3LYP was used as a functional. 6-31G(d,p) was used as a basis function. Table 11 shows the results.
  • the condensed ring compound C of the present disclosure exhibits a sufficiently low reorientation energy compared to DNTT.
  • reorientation energy and hole mobility are well correlated.
  • reorientation energy and hole mobility exhibit a negative correlation.
  • the fused ring compound C of the present disclosure has a higher hole mobility than DNTT. From this, it can be said that the condensed ring compound C is suitable for a semiconductor material.
  • the condensed ring compound C of the present disclosure tends to have excellent carrier mobility. Therefore, the condensed ring compound C is suitable for semiconductor materials.
  • the condensed ring compound C is useful as a p-type semiconductor material.
  • the semiconductor material S containing the condensed ring compound C can be used for electronic devices. By using the condensed ring compound C in an electronic device, the frequency characteristics of the electronic device can be improved.
  • a specific example of the electronic device is a transistor.

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