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  • H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
  • H10K85/211—Fullerenes, e.g. C60
  • H10K85/215—Fullerenes, e.g. C60 comprising substituents, e.g. PCBM
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  • C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
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  • C07C22/02—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings
  • C07C22/04—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings containing six-membered aromatic rings
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  • C07C23/18—Polycyclic halogenated hydrocarbons
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  • C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
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  • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
  • H10K30/60—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation in which radiation controls flow of current through the devices, e.g. photoresistors
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  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K39/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic radiation-sensitive element covered by group H10K30/00
  • H10K39/30—Devices controlled by radiation
  • H10K39/32—Organic image sensors
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  • C07—ORGANIC CHEMISTRY
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  • C07C2604/00—Fullerenes, e.g. C60 buckminsterfullerene or C70
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  • H10K30/30—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
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  • Y02E10/00—Energy generation through renewable energy sources
  • Y02E10/50—Photovoltaic [PV] energy
  • Y02E10/549—Organic PV cells

Definitions

• the present invention relates to a fullerene derivative, a thin film, a photoelectric conversion element, a solid-state imaging device, and a method for producing a fullerene derivative.
• Fullerene is a closed-shell molecule made of carbon, and is used in various fields due to its stable structure, high absorption characteristics, and good electrical characteristics.
• various fullerene derivatives in which a substituent is bonded to fullerene have also been developed.
• the photoelectric conversion element is an element that converts light into an electric signal by utilizing the photoelectric effect, includes a photoelectric diode, an optical transistor, and the like, and can be applied to an electronic device such as a solid-state imaging device. Therefore, in the development of photoelectric conversion elements, a technique using fullerenes or derivatives thereof having high absorption characteristics and good electrical characteristics has attracted attention, and the development of such elements has become an issue.
• Patent Document 2 discloses a photoelectric conversion element.
• Patent Document 1 discloses a fullerene derivative having a plurality of branched alkyl chains showing sublimation properties.
• Non-Patent Document 1 describes a fullerene derivative (60-2-1 etc.) having a plurality of trifluoromethyl groups. In addition, Non-Patent Document 1 also describes a fullerene derivative (C 60 CF 2 ) having a difluoromethano structure.
• the fullerene derivative has a structure in which the fusion ring of the pentagonal ring and the aromatic ring is substituted with a substituent, so that the steric hindrance is increased and the pi-conjugated system is reduced as compared with the unsubstituted fullerene. Can be done.
• fullerene derivatives can reduce fullerene aggregation during deposition and improve film formation properties compared to unsubstituted fullerenes, such as deformations in the absorption wavelength region that may occur due to aggregation. Deformation of optical characteristics can be effectively reduced.
• fullerene derivatives have a problem that they are thermally decomposed when heated for vapor deposition. Further, even a fullerene derivative exhibiting sublimation property has problems that the sublimation temperature is too high and synthesis is difficult.
• the fullerene derivative listed in the synthesis example of Patent Document 1 has a relatively high sublimation temperature of 400 ° C. or higher and is close to the decomposition temperature of this derivative, so that it is difficult to stably deposit the fullerene derivative.
• the fullerene derivative having a trifluoromethyl group described in Non-Patent Document 1 has a low sublimation temperature of less than 400 ° C., it is not suitable for mass production because it uses a special reaction device for synthesis. Further, the fullerene derivative having a difluoromethano structure described in Non-Patent Document 1 has a high sublimation temperature and is not practical.
• the present invention has been made in view of the above circumstances, and an object of the present invention is to provide a fullerene derivative which can be synthesized without the need for a special synthesis device and can be vapor-deposited at a low temperature without thermal decomposition. be. Another object of the present invention is to provide a photoelectric element containing the fullerene derivative and an image sensor including the photoelectric element.
• the present invention provides the following means for solving the above problems.
• the first aspect of the present invention provides the following fullerene derivatives.
• the fullerene derivative of the first aspect of the present invention preferably has the following characteristics. It is also preferable to combine two or more of the following features.
• a third aspect of the present invention provides the following solid-state image sensor. [7] A solid-state image sensor having the photoelectric conversion element according to the previous item [6].
• a fourth aspect of the present invention provides the following method for producing a fullerene derivative. [8] The method for producing a fullerene derivative according to any one of the above items [1] to [4].
• a method for producing a fullerene derivative which comprises a step of reacting a compound represented by (1) in the presence of a base.
• the fullerene derivative of the present invention can be synthesized without using a special reaction device, and further sublimates at a low temperature without thermal decomposition, so that it is useful as a fullerene derivative used for film formation by a vapor deposition method.
• the configuration of an example of a preferred embodiment of the present invention will be described below.
• the present invention can be appropriately modified and carried out without changing the gist thereof.
• the number, material, quantity, shape, numerical value, ratio, position, configuration, etc. can be changed, added, omitted, replaced, combined, etc. within the range not deviating from the gist of the present invention.
• the fullerene derivative of the present embodiment is a compound having a partial structure represented by the formula (1) in the fullerene skeleton.
• the "fullerene derivative” means a compound having a structure in which a specific group is added to these fullerene skeletons, and the “fullerene skeleton” is a carbon skeleton constituting a closed shell structure derived from fullerene. To say.
• C * is a carbon atom adjacent to each other forming a fullerene skeleton
• Rf 1 and Rf 2 are independently perfluoroalkyl groups having 1 to 4 carbon atoms, respectively, and Rf 1 and Rf 2 and Rf 2 may be connected to each other to form a ring structure.
• the fullerene derivative of the present embodiment has the structure of the above formula (1) in which a perfluoro group is bonded to the fullerene skeleton via a methano group. Therefore, it has a characteristic that the sublimation temperature is low, and is suitably used for film formation by thin film deposition.
• Rf 1 and Rf 2 are perfluoroalkyl groups, respectively, and have 1 to 4 carbon atoms.
• the carbon number may be, for example, 1 to 2 or 3 to 4.
• the carbon atoms of Rf 1 and Rf 2 may be the same or different. If the number of carbon atoms is larger than 4, the obtained fullerene derivative may be melted at the time of heating and may not be sublimated.
• the formed ring structure is preferably a 3- to 9-membered ring, preferably a 5- to 7-membered ring. For example, it may be a 4- to 8-membered ring, a 6 to 7-membered ring, or the like, if necessary.
• Rf 1 and Rf 2 include trifluoromethyl group, pentafluoroethyl group, heptafluoropropyl group, heptafluoroisopropyl group, nonafluorobutyl group, nonafluoroisobutyl group, nonafluoro-sec-butyl group and nonafluoro-. Examples thereof include a tert-butyl group.
• a trifluoromethyl group is particularly preferable from the viewpoint of easy availability of raw materials.
• Rf 1 and Rf 2 are linked to each other to form a ring structure include an octafluorobutylene group, a decafluoropentene group, and a dodecafluorohexene group.
• the fullerene skeleton in the fullerene derivative of the present embodiment can be arbitrarily selected, but the fullerene skeleton preferably has 60 to 200 carbon atoms.
• the number of carbon atoms may be 60 to 150, 60 to 100, 60 to 90, 60 to 80, 60 to 70, or the like, if necessary.
• Specific examples of the fullerene skeleton include C 60 , C 70 , C 76 , C 78 , C 82 , C 84 , C 90 , C 94 , C 96 , C 120 , C 200 , and the like, and among them, C 60 .
• C 70 , C 74 , C 76 or C 78 are more preferred, C 60 or C 70 is even more preferred, and C 60 is particularly preferred. This is because it is easier to obtain high-purity fullerene as a raw material when the number of carbon atoms is small, and in particular, C60 is easier to obtain higher-purity than other fullerenes.
• the fullerene derivative of the present embodiment has the above-mentioned structure, the sublimation temperature can be lowered, and therefore, the fullerene derivative can be vapor-deposited by sublimation without being decomposed. From the viewpoint that the sublimation temperature can be lowered, it is more preferable that the number of the partial structures represented by the above formula (1) is plural for one fullerene skeleton, and on the other hand, from the viewpoint of avoiding the complexity of synthesis and purification. Therefore, it is preferable that the number is one.
• the number of partial structures represented by the above formula (1) may be, for example, 1 to 50, 1 to 30, 1 to 20, 1 to 10, 1 to 5, 1 to 3, or 1 to 3, depending on the need. It may be 1 to 2 or only 1.
• thermogravimetric analysis it is usually possible if the temperature at which a weight loss of 10% with respect to the initial weight occurs is 400 ° C. or less in a nitrogen atmosphere, and the temperature at which a weight loss of 50% with respect to the initial weight occurs is 400 ° C. or less. If there is, it is possible more surely.
• the lower limit of these temperatures can be arbitrarily selected, and examples thereof include, but are not limited to, 200 ° C. or higher.
• the temperature at which the weight loss of 10% occurs is, for example, 400 ° C. or lower, 380 ° C. or lower, 360 ° C. or lower, 340 ° C.
• the temperature at which the weight loss of 50% with respect to the initial weight occurs is, for example, 400 ° C. or lower, 380 ° C. or lower, 360 ° C. or lower, 340 ° C. or lower, 320 ° C. or lower, 300 ° C. or lower, or 280 ° C. or lower. There may be.
• the temperature at which the 10% weight loss occurs is lower than the temperature at which the 50% weight loss occurs. The difference between these temperatures can be arbitrarily selected, but may be, for example, 45 to 65 ° C, 40 to 60 ° C, 35 to 55 ° C, or the like.
• the method for producing the fullerene derivative of the present embodiment is not particularly limited, and examples thereof include the following methods. That is, fullerene and the compound represented by the formula (2) are reacted in the presence of a base to obtain a fullerene derivative represented by the formula (1).
• X represents a halogen atom
• Rf 1 and Rf 2 are the same as those shown in the formula (1).
• the fullerene used in the reaction can be arbitrarily selected, but the number of carbon atoms is preferably 60 to 200.
• the number of carbon atoms may be 60 to 150, 60 to 100, 60 to 90, 60 to 80, 60 to 70, or the like, if necessary.
• Specific examples of fullerenes include C 60 , C 70 , C 76 , C 78 , C 82 , C 84 , C 90 , C 94 , C 96 , C 120 , C 200 , and the like, and among them, C 60 , C 70 , C 74 , C 76 or C 78 is more preferred, C 60 or C 70 is even more preferred, and C 60 is particularly preferred.
• X represents a halogen atom
• examples of the halogen atom include chlorine, bromine, iodine and the like, and X is preferably iodine from the viewpoint of reactivity.
• Preferred examples of Rf 1 and Rf 2 are the same as those in the above formula (1).
• a solvent may be used for this reaction, and the reaction is not particularly limited, but one that dissolves fullerene and the compound of the above formula (2) is preferable.
• the reaction is not particularly limited, but one that dissolves fullerene and the compound of the above formula (2) is preferable.
• benzene, toluene, xylene, trimethylbenzene, chlorobenzene, 1,2-dichlorobenzene and the like can be mentioned. Of these, 1,2-dichlorobenzene is preferable because the solubility of fullerene and the compound of the above formula (2) is high.
• the base is not particularly limited, but is, for example, a metal hydroxide such as sodium hydroxide and potassium hydroxide, a metal carbonate such as sodium carbonate, potassium carbonate and cesium carbonate, sodium ethoxyoxide and potassium ethoxyde.
• a metal hydroxide such as sodium hydroxide and potassium hydroxide
• a metal carbonate such as sodium carbonate, potassium carbonate and cesium carbonate
• sodium ethoxyoxide and potassium ethoxyde examples thereof include metal alkoxides such as potassium-tert-butoxide, organic bases such as pyridine, triethylamine, and diazabicycloundecene, and among them, potassium-tert-butoxide is preferable because of its excellent reaction yield.
• the base may be used alone or in combination of two or more.
• the amount of the base can be arbitrarily selected, and examples thereof include 0.01 to 100 molar equivalents with respect to the compound represented by the formula (2).
• phase transfer catalyst may be used for the purpose of increasing the solubility of the base in the solvent and increasing the reaction rate.
• the phase transfer catalyst include crown ethers such as 18-crown-6-ether and 15-crown-5-ether, and polyalkylene glycols such as polyethylene glycol dimethyl ether. Crown ethers are preferable because they have a strong effect of increasing the reaction rate, and 15-crown-5-ether is particularly preferable.
• the phase transfer catalyst may be used alone or in combination of two or more.
• the amount of the base can be arbitrarily selected, and examples thereof include 0.01 to 500 molar equivalents with respect to the compound represented by the formula (2).
• the reaction temperature of this reaction the higher the reaction temperature, the easier the reaction proceeds, and the lower the reaction temperature, the higher the reaction selectivity and the higher the yield of the target product.
• the reaction temperature may be selected according to the purpose. Usually, it is preferable to select from ⁇ 50 ° C. to the boiling point of the solvent used, and more preferably to select the temperature between ⁇ 20 ° C. and 50 ° C.
• the reaction temperature of this reaction is -50 ° C to -20 ° C, -20 ° C to -5 ° C, -5 ° C to 0 ° C, 0 ° C to 10 ° C, 10 to 30 ° C, if necessary. Or 30 ° C to 50 ° C, for example.
• the reaction time of this reaction it is better to carry out for a long time until the reaction proceeds sufficiently in order to obtain a high yield. In order to increase the production amount, it is better to complete one reaction in a short time and repeat such a reaction a plurality of times before the reaction rate slows down. From this point of view, the reaction time may be selected according to the purpose, but is usually preferably selected between 1 minute and 120 hours, and more preferably between 5 minutes and 24 hours. , 30 minutes to 12 hours are more preferred.
• the pressure at the time of reaction is not particularly limited and may or may not be pressurized.
• the pressure can be preferably selected from, for example, normal pressure to 10 atm.
• the reaction at normal pressure is preferable from the viewpoint that the cost can be kept low without requiring a special device such as a pressurizing facility.
• the order in which the fullerene, the compound represented by the formula (2), the base, and the solvent are mixed can be arbitrarily selected. For example, fullerene may be dissolved in a solvent, and then the compound represented by the formula (2) and a base may be further added and mixed. However, it is not limited to this example.
• the thin film of the present embodiment contains the fullerene derivative.
• the thin film may be formed by any method such as a wet film forming method such as spin coating or slit coating, or a dry film forming method such as thin film deposition, but it is preferably formed by thin film deposition.
• the thin film may be composed of only the fullerene derivative of the present embodiment, or may be composed of a mixture with other compounds.
• the thin film of the present embodiment can easily maintain the inherent properties of the fullerene derivative as it is without damaging the chemical bond of the fullerene derivative.
• the optical characteristics can be improved as compared with the non-substituted fullerene (for example, C60) thin film in which aggregation is likely to occur during film formation, and further, the characteristics of the photoelectric conversion element and the solid-state image sensor described later can be improved. Can also be improved.
• the absorption characteristics of the thin film containing the fullerene derivative of the present embodiment are different from the light absorption characteristics of the thin film containing the unsubstituted fullerene.
• the thin film containing the fullerene derivative of the present embodiment reduces the abnormal absorption of visible light in the short wavelength region of about 400 nm to 500 nm. It is considered that the abnormal absorption is caused by the aggregation of fullerene or fullerene derivative.
• the extinction coefficient of the thin film containing the fullerene derivative of the present embodiment at a wavelength of 450 nm is smaller than the extinction coefficient of the thin film containing an unsubstituted fullerene at a wavelength of 450 nm.
• the extinction coefficient of a thin film containing a fullerene derivative at a wavelength of 450 nm is about 1 ⁇ 2 or less of the extinction coefficient of a thin film containing an unsubstituted fullerene at a wavelength of 450 nm.
• the photoelectric conversion element of the present embodiment has a first electrode and a second electrode facing each other, and an organic layer arranged between the two electrodes.
• the organic layer contains a fullerene derivative represented by the formula (1). Further, the organic layer may contain other compounds in addition to the fullerene derivative.
• the first electrode and the second electrode are not particularly limited, and known materials and the like can be used.
• the structure of the photoelectric conversion element of the present embodiment is not particularly limited as long as it has the above-mentioned characteristics. Examples of the structure of the photoelectric conversion element include the element structure described in Patent Document 2.
• the solid-state image sensor (image sensor) of the present embodiment has one or more photoelectric conversion elements. Further, the solid-state image sensor is applied to various electronic devices, and may be preferably applied to, for example, mobile phones, digital cameras, and the like, but is not limited thereto.
• reaction mixture was purified by preparative HPLC (column: COSMOSIL PBB (inner diameter 20 mm, length 250 mm) manufactured by Nacalai Tesque, eluent: toluene) to obtain a fraction containing compound 1a and a fraction containing compound 1b. Obtained.
• the solvent was distilled off, and the obtained solid was washed with methanol and dried to obtain 84 mg of compound 1a and 40 mg of compound 1b, respectively, as a brown solid.
• the chemical formula of compound 1a is shown as (C1a)
• the chemical formula of compound 1b is shown as (C1b).
• Compound 1b is a mixture of isomers having different positions to which the substituent is added.
• Example 1-1 Thermogravimetric analysis of compound 1a in vacuum was carried out in order to confirm whether or not the compound 1a could be vapor-deposited by sublimation and the sublimation temperature.
• the sample (about 5 mg) was set in a vacuum thermogravimetric analyzer (VPE-9000 manufactured by Advance Riko Co., Ltd.). The temperature was raised from room temperature to 1000 ° C. at a rate of 10 ° C./min in a vacuum of 1 Pa or less.
• Ts ° C.
• -10% the temperature when the weight decreased by 50% was defined as Ts (° C.) (-50%).
• the results are shown in Table 1.
• Example 1 (Examples 1-2 to 1-6, Comparative Examples 1-1 to 1-4) Thermogravimetric analysis was carried out in the same manner as in Example 1 except that the compounds shown in Table 1 were used instead of the compound 1a. The results are shown in Table 1.
• the fullerene derivative of the present invention is the unsubstituted fullerene (C 60 ) of Comparative Example 1-1. It can be seen that sublimation is possible at a lower temperature. Further, when Example 1-6 having a fullerene skeleton of C 70 is compared with Comparative Example 1-4, it can be seen that the same tendency is observed even if the fullerene skeleton is C 70 .
• the fullerene derivative of the present invention is at a lower temperature than the fullerene derivative conventionally known to sublimate. It turns out that it can be sublimated.
• Example 2-1 Compound 1a was vapor-deposited on a glass substrate, and the absorption characteristics of the vapor-deposited thin film were evaluated.
• the thin film was prepared by depositing the thin film on a dry glass substrate washed with isopropyl alcohol (IPA) and acetone using an ultrasonic washer at a rate of 0.1 to 1.0 ⁇ / s under high vacuum.
• IPA isopropyl alcohol
• the absorption characteristics were evaluated by the absorption coefficient at 450 nm using a UV-Vis spectrophotometer (UV-2400 manufactured by Shimadzu Corporation). The results are shown in Table 2.
• Example 2-2 to 2-6 Comparative Examples 2-1 to 2-2
• the absorption characteristics were evaluated in the same manner as in Example 2-1 except that the compounds shown in Table 2 were used instead of the compound 1a. The results are shown in Table 2.
• the thin film containing the fullerene derivative in which the fullerene skeleton of the present invention is C 60 is compared with the thin film containing the unsubstituted fullerene C 60 (Comparative Example 2-1). It can be seen that the extinction coefficient at 450 nm is small. Further, the thin film containing a fullerene derivative having a fullerene skeleton of C 70 (Example 2-6) of the present invention absorbs light at 450 nm as compared with a thin film containing an unsubstituted fullerene C 70 (Comparative Example 2-2). It can be seen that the coefficient is small. From this, it can be confirmed that the fullerene derivative of the present invention does not exhibit abnormal absorption characteristics in the short wavelength region of visible light due to aggregation.
• fullerene derivative that can be synthesized without the need for a special synthesis device and can be vapor-deposited at a low temperature without thermal decomposition.
• the fullerene derivative of the present invention can be preferably used for a photoelectric element, a solid-state image pickup device, or the like.

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