WO2022209892A1 - 電荷輸送性ワニス - Google Patents
電荷輸送性ワニス Download PDFInfo
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- WO2022209892A1 WO2022209892A1 PCT/JP2022/011838 JP2022011838W WO2022209892A1 WO 2022209892 A1 WO2022209892 A1 WO 2022209892A1 JP 2022011838 W JP2022011838 W JP 2022011838W WO 2022209892 A1 WO2022209892 A1 WO 2022209892A1
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- 150000003518 tetracenes Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(II) oxide Inorganic materials [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 125000005369 trialkoxysilyl group Chemical group 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- FQYWWLSIKWDAEC-UHFFFAOYSA-N tributoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)CCCOCC1CO1 FQYWWLSIKWDAEC-UHFFFAOYSA-N 0.000 description 1
- 125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- UNKMHLWJZHLPPM-UHFFFAOYSA-N triethoxy(oxiran-2-ylmethoxymethyl)silane Chemical compound CCO[Si](OCC)(OCC)COCC1CO1 UNKMHLWJZHLPPM-UHFFFAOYSA-N 0.000 description 1
- OHKFEBYBHZXHMM-UHFFFAOYSA-N triethoxy-[1-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCO[Si](OCC)(OCC)C(CCC)OCC1CO1 OHKFEBYBHZXHMM-UHFFFAOYSA-N 0.000 description 1
- SJQPASOTJGFOMU-UHFFFAOYSA-N triethoxy-[1-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CCO[Si](OCC)(OCC)C(C)OCC1CO1 SJQPASOTJGFOMU-UHFFFAOYSA-N 0.000 description 1
- NFRRMEMOPXUROM-UHFFFAOYSA-N triethoxy-[1-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)C(CC)OCC1CO1 NFRRMEMOPXUROM-UHFFFAOYSA-N 0.000 description 1
- FVMMYGUCXRZVPJ-UHFFFAOYSA-N triethoxy-[2-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCO[Si](OCC)(OCC)CC(CC)OCC1CO1 FVMMYGUCXRZVPJ-UHFFFAOYSA-N 0.000 description 1
- RWJUTPORTOUFDY-UHFFFAOYSA-N triethoxy-[2-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CCO[Si](OCC)(OCC)CCOCC1CO1 RWJUTPORTOUFDY-UHFFFAOYSA-N 0.000 description 1
- CFUDQABJYSJIQY-UHFFFAOYSA-N triethoxy-[2-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CC(C)OCC1CO1 CFUDQABJYSJIQY-UHFFFAOYSA-N 0.000 description 1
- KPNCYSTUWLXFOE-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCO[Si](OCC)(OCC)CCC(C)OCC1CO1 KPNCYSTUWLXFOE-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- GSUGNQKJVLXBHC-UHFFFAOYSA-N triethoxy-[4-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCCOCC1CO1 GSUGNQKJVLXBHC-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- DAVVOFDYOGMLNQ-UHFFFAOYSA-N trimethoxy-[1-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CO[Si](OC)(OC)C(C)OCC1CO1 DAVVOFDYOGMLNQ-UHFFFAOYSA-N 0.000 description 1
- FNBIAJGPJUOAPB-UHFFFAOYSA-N trimethoxy-[1-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)C(CC)OCC1CO1 FNBIAJGPJUOAPB-UHFFFAOYSA-N 0.000 description 1
- ZNXDCSVNCSSUNB-UHFFFAOYSA-N trimethoxy-[2-(oxiran-2-ylmethoxy)ethyl]silane Chemical compound CO[Si](OC)(OC)CCOCC1CO1 ZNXDCSVNCSSUNB-UHFFFAOYSA-N 0.000 description 1
- HTVULPNMIHOVRU-UHFFFAOYSA-N trimethoxy-[2-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CC(C)OCC1CO1 HTVULPNMIHOVRU-UHFFFAOYSA-N 0.000 description 1
- ZQPNGHDNBNMPON-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CO[Si](OC)(OC)CCC(C)OCC1CO1 ZQPNGHDNBNMPON-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- GUKYSRVOOIKHHB-UHFFFAOYSA-N trimethoxy-[4-(oxiran-2-ylmethoxy)butyl]silane Chemical compound CO[Si](OC)(OC)CCCCOCC1CO1 GUKYSRVOOIKHHB-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Images
Classifications
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
- H10K50/155—Hole transporting layers comprising dopants
-
- 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
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- 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
Definitions
- the present invention relates to a charge-transporting varnish.
- Organic functional films made of organic compounds are used as light-emitting layers and charge injection layers in organic electroluminescence (hereinafter referred to as organic EL) devices.
- the hole-injecting layer carries out charge transfer between the anode and the hole-transporting layer or the light-emitting layer, and plays an important role in achieving low-voltage driving and high luminance of the organic EL device.
- the method of forming the hole injection layer is broadly divided into a dry process typified by vapor deposition and a wet process typified by spin coating. It is possible to efficiently manufacture a thin film with high resistance.
- Patent Document 1 proposes a technology related to a hole injection material that can be formed by a wet process.
- the coloration of the charge-transporting thin film used in the organic EL device reduces the color purity and color reproducibility of the organic EL device. It is desired to have a high modulus and high transparency.
- the present applicant has already reported that a highly transparent charge-transporting thin film can be obtained by adding metal oxide nanoparticles such as silica or zirconia to a composition for forming a charge-transporting thin film. (See Patent Documents 2 and 3).
- the present invention has been made in view of the above circumstances, and an object of the present invention is to provide a charge-transporting varnish that provides a charge-transporting thin film with excellent transparency and electrical properties.
- the present inventors have made intensive studies to solve the above problems, and as a result, using a charge-transporting varnish containing metal oxide nanoparticles surface-treated with a silane coupling agent having a conductive functional group, The inventors have found that a charge-transporting thin film having excellent transparency and electrical properties can be obtained, and completed the present invention.
- a charge-transporting varnish comprising a charge-transporting substance, a dopant substance, metal oxide nanoparticles surface-treated with a silane coupling agent having a conductive functional group, and a solvent; 2. 1 charge-transporting varnish, wherein the silane coupling agent is a compound represented by the following formula (S1); (In the formula, R represents an alkyl group having 1 to 10 carbon atoms, A 1 represents a single bond or an alkylene group having 1 to 10 carbon atoms, A 2 represents a single bond or a divalent group other than an alkylene group. represents a linking group , and A3 represents a monovalent organic group having a conductive functional group.) 3.
- S1 silane coupling agent
- R represents an alkyl group having 1 to 5 carbon atoms
- a 1 represents an alkylene group having 2 to 5 carbon atoms
- a 2 represents -O-, -S-, -NH-, an amide bond, or 2 charge-transporting varnishes representing a urea bond
- a 3 representing an aryl group having a phenylcarbazole structure
- the silane coupling agent is a compound represented by the following formula (S1-1); (In the formula, R represents an alkyl group having 1 to 5 carbon atoms, A 1 represents an alkylene group having 2 to 5 carbon atoms, and A 4 represents an arylene group.) 5.
- the charge-transporting varnish of the present invention contains metal oxide nanoparticles surface-treated with a silane coupling agent having a conductive functional group, it only provides a charge-transporting thin film with excellent transparency and electrical properties. In addition, even when the amount of metal oxide nanoparticles added is increased, a charge-transporting thin film is provided in which degradation of electrical properties is suppressed while maintaining transparency, which is the effect of particle addition.
- the charge-transporting varnish of the present invention having such properties can be suitably used for producing thin films for electronic devices such as organic EL devices, particularly thin films for organic EL displays.
- FIG. 4 is a graph showing the average transmittance of 400 to 800 nm of quartz substrates with 50 nm thin films obtained in Examples 2-1 and 2-2 and Comparative Examples 2-1 and 2-2.
- FIG. 4 is a graph showing the average transmittance of 400 to 800 nm of quartz substrates with 100 nm thin films obtained in Examples 2-3 to 2-4 and Comparative Examples 2-3 to 2-4.
- FIG. 10 is a graph showing the average transmittance of 400 to 800 nm of quartz substrates with 50 nm thin films obtained in Examples 2-5 to 2-8 and Comparative Examples 2-5 to 2-6.
- the charge-transporting varnish according to the present invention comprises metal oxide nanoparticles surface-treated with a charge-transporting substance, a dopant substance, and a silane coupling agent having a conductive functional group (hereinafter referred to as surface-treated metal oxide nanoparticles sometimes referred to as) and a solvent.
- surface-treated metal oxide nanoparticles sometimes referred to as
- the term "charge-transporting property" has the same meaning as conductivity and the same meaning as hole-transporting property.
- the charge-transporting varnish may itself have charge-transporting properties, or the solid film obtained therefrom may have charge-transporting properties.
- the metal oxide nanoparticles surface-treated with a silane coupling agent having a conductive functional group, which is a characteristic component of the charge-transporting varnish of the present invention, are usually insulating. It is possible to form a conductive path with a charge-transporting substance by treating the surface of metal oxide nanoparticles, which are objects, with a silane coupling agent having a conductive functional group.
- the nanoparticles mean fine particles whose primary particles have an average particle size on the order of nanometers (typically 500 nm or less).
- Metal oxide nanoparticles refer to metal oxides shaped into nanoparticles.
- the primary particle size of the metal oxide nanoparticles is not particularly limited as long as it is nano-sized, but it is usually 5 nm or more, from the viewpoint of ensuring good dispersibility of the particles, ease of production, etc. Therefore, it is usually 200 nm or less, preferably 100 nm or less, more preferably 30 nm or less.
- the metals constituting the metal oxide nanoparticles include not only metals in the usual sense, but also semimetals.
- Metals in the usual sense include, but are not limited to, tin (Sn), titanium (Ti), aluminum (Al), zirconium (Zr), zinc (Zn), niobium (Nb), tantalum ( One or more selected from the group consisting of Ta) and W (tungsten).
- metalloids refer to elements whose chemical and/or physical properties are intermediate between those of metals and nonmetals. A universal definition of metalloids has not been established, but in the present invention, a total of six Let the elements be semimetals. These semimetals may be used alone or in combination of two or more, and may also be used in combination with metals in the usual sense.
- metal oxide nanoparticles include boron (B), silicon (Si), germanium (Ge), arsenic (As), antimony (Sb), tellurium (Te), tin (Sn), titanium (Ti), aluminum It preferably contains one or more metal oxides selected from (Al), zirconium (Zr), zinc (Zn), niobium (Nb), tantalum (Ta) and W (tungsten).
- the metal oxide may be a mixture of oxides of individual single metals, or a composite oxide containing a plurality of metals.
- metal oxides include B2O3 , B2O , SiO2 , SiO, GeO2 , GeO , As2O4 , As2O3 , As2O5 , Sb2O3 , Sb2 . O5, TeO2, SnO2 , ZrO2 , Al2O3 , ZnO and the like, but also B2O3 , B2O , SiO2 , SiO , GeO2 , GeO , As2O4 , As2 . O3 , As2O5 , SnO2 , SnO, Sb2O3, TeO2 , TiO2 and mixtures thereof are preferred, and SiO2 and ZrO2 are more preferred.
- silane coupling agent having a conductive functional group used as a surface treatment agent for example, a silane coupling agent having an alkoxysilyl group and a conductive functional group can be used.
- a silane coupling agent having a group is preferable, and a compound having a trialkoxysilyl group represented by the following formula (S1) is preferably used.
- R represents an alkyl group having 1 to 10 carbon atoms
- a 1 represents a single bond or an alkylene group having 1 to 10 carbon atoms
- a 2 represents a single bond or two other than an alkylene group.
- a 3 represents a monovalent organic group having a conductive functional group.
- the alkyl group having 1 to 10 carbon atoms for R may be linear, branched or cyclic, and specific examples thereof include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and sec-butyl.
- alkyl having 1 to 5 carbon atoms is preferred, an alkyl group having 1 to 3 carbon atoms is more preferred, and a methyl group and an ethyl group are even more preferred.
- the alkylene group having 1 to 10 carbon atoms for A 1 may be linear, branched or cyclic, and specific examples include methylene, ethylene, propylene, trimethylene, tetramethylene, pentamethylene, hexamethylene and hepta. Examples thereof include methylene, octamethylene, nonamethylene, and decylene groups. Among these, an alkylene group having 2 to 5 carbon atoms is preferable, an alkyl group having 2 to 4 carbon atoms is more preferable, and an ethylene group and a trimethylene group are more preferable. preferable.
- Examples of the divalent linking group for A 2 include -O-, -S-, -O-(CH 2 ) k -O-, -S-(CH 2 ) k -S-, -O-(CH 2 ) k —S—, —S—(CH 2 ) k —O— (in these formulas, k represents an integer of 1 to 5), —NH—, —CO—, —NHCO—, —CONH -, -SO 2 NH-, -NHSO 2 -, -NHCONH-, -COO-, -OCO-, 2,5-pyrrolidinedione rings represented by the following formula (A2-1), etc., but these Among them, -O-, -S-, -NH-, an amide bond (-NHCO-, -CONH-) or a urea bond (-NHCONH-) is preferred.
- the monovalent organic group having a conductive functional group for A 3 may be a monovalent group containing a chemical structure conventionally known as a structure that exhibits conductivity.
- a valent group, a monovalent group having a triarylamine structure, a monovalent group having an N,N'-diarylbenzidine structure, and a monovalent group having an N,N,N',N'-tetraarylbenzidine structure a monovalent group having a carbazole structure, a monovalent group having an oligothiophene structure, a monovalent group having a thienothiophene structure, a monovalent group having a thienobenzothiophene structure, a monovalent group having an oligopyrrole structure and the like, preferably an aryl group having one or more of these conductive functional groups, more preferably an aryl group having a triarylamine structure, an aryl group having a carbazole structure, and an aryl having a phenyl
- monovalent organic group having a conductive functional group examples include, but are not limited to, those represented by the following formulae. Among these, groups represented by formulas (A3-9) and (A3-10) are preferred.
- a 4 represents an arylene group, preferably an arylene group having 6 to 40 carbon atoms.
- Specific examples of the arylene group include, but are not limited to, those represented by the following formulas.
- arylene group those having the bond at the following positions are particularly suitable.
- the silane coupling agent used in the present invention is preferably a compound represented by the following formula (S1-1), more preferably a compound represented by the following formula (S1-1-1).
- R represents an alkyl group having 1 to 5 carbon atoms
- a 1 represents an alkylene group having 2 to 5 carbon atoms
- a 4 represents an arylene group.
- R represents an alkyl group having 1 to 5 carbon atoms
- a 1 represents an alkylene group having 2 to 5 carbon atoms
- a 4 represents an arylene group.
- silane coupling agents include, but are not limited to, those represented by the following formulas.
- the silane coupling agent includes a trialkoxysilane compound having a halogen atom, NCO, NH 2 , SH, a reactive group such as a 2,5-dioxotetrahydro-3-yl group at the terminal, and An aryl compound having a functional group ( NH2 group, NCO group, carboxylic acid halide group, sulfonic acid halide group, etc.) that reacts with these reactive groups is subjected to a divalent reaction such as amidation, ureaization, or esterification. It can be obtained by reacting with a known method for forming a linking group.
- alkoxysilane compounds used in the production of the silane coupling agent used in the present invention include 3-isocyanatopropyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane, 3-mercaptopropyltrimethoxysilane, and 3-mercaptopropyltriethoxysilane.
- glycidoxymethyltriethoxysilane ⁇ -glycidoxyethyltrimethoxysilane, ⁇ -glycidoxyethyltriethoxysilane, ⁇ -glycidoxyethyltrimethoxysilane, ⁇ -glycidoxyethyltriethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropyltriethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropyltriethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropyltriethoxysilane, ⁇ -glycidoxypropyltrimethoxysilane, ⁇ -glycidoxypropyltriethoxysilane, ⁇ -glycidoxypropyltriethoxysilane,
- the primary particle size of the surface-treated metal oxide nanoparticles is not particularly limited, but is usually 5 nm or more, and is usually 200 nm or less, preferably 200 nm or less, from the viewpoint of ensuring good dispersibility of the particles, ease of production, etc. It is 100 nm or less, more preferably 30 nm or less.
- This particle diameter is the particle diameter (median diameter D 50 ) at which the cumulative frequency distribution in the volume-based particle size distribution measurement by the dynamic light scattering method is 50%.
- the amount of modification of the silane coupling agent on the surface of the metal oxide nanoparticles is not particularly limited, but the dispersibility of the metal oxide nanoparticles and the resulting thin film From the viewpoint of the transparency of the 2 is even more preferred.
- the modification amount X (number/nm 2 ) is the specific surface area SA (nm 2 /g) of one particle calculated from the particle size (nm) and specific gravity (g/cm 3 ) of the metal oxide nanoparticles.
- the amount of metal oxide nanoparticles contained in the charge-transporting varnish of the present invention is not particularly limited. In minutes, the lower limit is generally 20% by mass, preferably 30% by mass, more preferably 40% by mass, and the upper limit is generally 95% by mass, preferably 90% by mass.
- the surface-treated metal oxide nanoparticles used in the present invention may be used in the form of a sol dispersed in a dispersion medium.
- dispersion media include water, methanol, methyl ethyl ketone, methyl isobutyl ketone, N,N-dimethylacetamide, ethylene glycol, isopropanol, methanol, ethylene glycol monopropyl ether, cyclohexanone, ethyl acetate, toluene, and propylene glycol monomethyl ether acetate. etc.
- the solid content concentration of the sol is not particularly limited, but is preferably 5 to 60% by mass, more preferably 10 to 50% by mass, and even more preferably 15 to 30% by mass.
- the amount of the sol to be used is appropriately determined in consideration of the concentration thereof so that the amount of the surface-treated metal oxide nanoparticles finally contained in the varnish is the above-described compounded amount of the metal oxide nanoparticles.
- Charge-transporting substance is not particularly limited, and is appropriately selected from, for example, charge-transporting compounds, charge-transporting oligomers, charge-transporting polymers, etc. used in the field of organic EL.
- charge-transporting compounds such as charge-transporting compounds, charge-transporting oligomers, charge-transporting polymers, etc. used in the field of organic EL.
- can be used as Specific examples thereof include arylamine derivatives such as oligoaniline derivatives, N,N'-diarylbenzidine derivatives, N,N,N',N'-tetraarylbenzidine derivatives; oligothiophene derivatives, thienothiophene derivatives, and thienobenzothiophene.
- Thiophene derivatives such as derivatives; various charge-transporting compounds such as pyrrole derivatives such as oligopyrrole; charge-transporting polymers such as charge-transporting oligomers, polythiophene derivatives, polyaniline derivatives, and polypyrrole derivatives; Derivatives, arylamine derivatives are preferred.
- a charge-transporting compound low-molecular-weight compound
- a charge-transporting oligomer such as a tertiary arylamine compound represented by formula (A1) or (A2) described later produces a thin film with high flatness. From this point of view, it is preferably monodispersed (that is, the molecular weight distribution is 1). In this case, the molecular weight of the charge-transporting substance is usually about 200 to 9,000 from the viewpoint of preparing a uniform ink that provides a thin film with high flatness.
- It is preferably 300 or more, more preferably 400 or more, and from the viewpoint of preparing a uniform ink that gives a highly flat thin film with good reproducibility, it is preferably 8,000 or less, more preferably 7,000 or less, and 6,000 or less. is more preferred, and 5,000 or less is even more preferred.
- Charge-transporting substances include, for example, JP-A-2002-151272, WO2004/105446, WO2005/043962, WO2008/032617, WO2008/032616, Publication No. 2013/042623, WO 2014/141998, WO 2014/185208, WO 2015/050253, WO 2015/137391, WO 2015/137395, WO 2015/146912, International Publication No. 2015/146965, International Publication No. 2016/190326, International Publication No. 2016/136544, International Publication No. 2016/204079 and the like.
- a preferred embodiment of the charge-transporting substance is a tertiary arylamine compound having at least one nitrogen atom and all nitrogen atoms having a tertiary arylamine structure. That is, this tertiary arylamine compound has at least one nitrogen atom and has a structure in which three aromatic groups are bonded to all the nitrogen atoms. It is preferable that the tertiary arylamine compound has two or more nitrogen atoms.
- Suitable examples of tertiary arylamine compounds include compounds represented by the following formula (A1) or (A2).
- R 1 and R 2 are each independently a hydrogen atom, a halogen atom, a nitro group or a cyano group, or an alkyl group having 1 to 20 carbon atoms optionally substituted with a halogen atom, carbon It is an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms.
- Halogen atoms include fluorine, chlorine, bromine, and iodine atoms.
- the alkyl group having 1 to 20 carbon atoms may be linear, branched or cyclic, and specific examples thereof include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert.
- - Linear or branched alkyl groups having 1 to 20 carbon atoms such as butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl groups; cyclopropyl, cyclobutyl, cyclopentyl , cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, bicyclobutyl, bicyclopentyl, bicyclohexyl, bicycloheptyl, bicyclooctyl, bicyclononyl, and bicyclodecyl groups.
- the alkenyl group having 2 to 20 carbon atoms may be linear, branched or cyclic, and specific examples include vinyl, n-1-propenyl, n-2-propenyl, 1-methylvinyl, n- 1-butenyl, n-2-butenyl, n-3-butenyl, 2-methyl-1-propenyl, 2-methyl-2-propenyl, 1-ethylvinyl, 1-methyl-1-propenyl, 1-methyl-2- propenyl, n-1-pentenyl, n-1-decenyl, n-1-eicosenyl groups and the like.
- the alkynyl group having 2 to 20 carbon atoms may be linear, branched or cyclic, and specific examples include ethynyl, n-1-propynyl, n-2-propynyl, n-1-butynyl, n -2-butynyl, n-3-butynyl, 1-methyl-2-propynyl, n-1-pentynyl, n-2-pentynyl, n-3-pentynyl, n-4-pentynyl, 1-methyl-n-butynyl , 2-methyl-n-butynyl, 3-methyl-n-butynyl, 1,1-dimethyl-n-propynyl, n-1-hexynyl, n-1-decynyl, n-1-pentadecynyl, n-1-eicosinyl and the like.
- Aryl groups having 6 to 20 carbon atoms include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9 -phenanthryl group and the like.
- Heteroaryl groups having 2 to 20 carbon atoms include 2-thienyl, 3-thienyl, 2-furanyl, 3-furanyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 3-isoxazolyl, 4-isoxazolyl, 5- isoxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 2-imidazolyl, 4-imidazolyl, 2-pyridyl, 3-pyridyl, 4-pyridyl groups, etc. .
- R 1 and R 2 are a hydrogen atom, a fluorine atom, a cyano group, an alkyl group having 1 to 20 carbon atoms which may be substituted with a halogen atom, and a number of carbon atoms which may be substituted with a halogen atom.
- An aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms which may be substituted with a halogen atom is preferable, and a hydrogen atom, a fluorine atom, a cyano group, or a carbon atom number which may be substituted with a halogen atom is 1.
- An alkyl group of up to 10 or a phenyl group optionally substituted with a halogen atom is more preferable, a hydrogen atom or a fluorine atom is even more preferable, and a hydrogen atom is most preferable.
- Ph 1 is a group represented by formula (P1).
- R 3 to R 6 are each independently a hydrogen atom, a halogen atom, a nitro group or a cyano group, or an alkyl group having 1 to 20 carbon atoms or alkenyl having 2 to 20 carbon atoms, which may be substituted with a halogen atom. an alkynyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms. Specific examples of these are the same as those mentioned in the description of R 1 and R 2 .
- R 3 to R 6 are a hydrogen atom, a fluorine atom, a cyano group, an alkyl group having 1 to 20 carbon atoms which may be substituted with a halogen atom, and a 20 aryl groups or heteroaryl groups having 2 to 20 carbon atoms which may be substituted with halogen atoms are preferred, hydrogen atoms, fluorine atoms, cyano groups, and 1 to 10 carbon atoms which may be substituted with halogen atoms or a phenyl group which may be substituted with a halogen atom, more preferably a hydrogen atom or a fluorine atom, most preferably a hydrogen atom.
- Suitable groups for Ph 1 include, but are not limited to, 1,4-phenylene groups.
- each Ar 1 is independently a group represented by any one of the following formulas (Ar1-1) to (Ar1-11), particularly the following formulas (Ar1-1′) to ( A group represented by any one of Ar1-11′) is preferred.
- R 7 to R 27 , R 30 to R 51 and R 53 to R 154 are each independently a hydrogen atom, a halogen atom, a nitro group or a cyano group, or a diphenylamino group optionally substituted with a halogen atom, It is an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an alkynyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms.
- R 28 and R 29 are each independently an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms, which may be substituted with Z 1 .
- R 52 is an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms which may be substituted with Z 1 .
- Z 1 is a halogen atom, a nitro group or a cyano group, or an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms or an alkynyl group having 2 to 20 carbon atoms which may be substituted with Z 2 is.
- Z 2 is an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms which may be substituted with a halogen atom, a nitro group or a cyano group, or Z 3 .
- Z 3 is a halogen atom, a nitro group or a cyano group.
- R 7 to R 27 , R 30 to R 51 and R 53 to R 154 are hydrogen atom, fluorine atom, cyano group, diphenylamino group optionally substituted with halogen atom, an alkyl group having 1 to 20 carbon atoms which may be optionally substituted, an aryl group having 6 to 20 carbon atoms which may be substituted by a halogen atom, or a heteroaryl group having 2 to 20 carbon atoms which may be substituted by a halogen atom
- a hydrogen atom, a fluorine atom, a cyano group, an alkyl group having 1 to 10 carbon atoms optionally substituted by a halogen atom, or a phenyl group optionally substituted by a halogen atom is more preferred, and a hydrogen atom or a fluorine atom. is more preferred, and a hydrogen atom is most suitable.
- R 28 and R 29 are preferably an aryl group having 6 to 14 carbon atoms which may be substituted with a halogen atom, or a heteroaryl group having 2 to 14 carbon atoms which may be substituted with a halogen atom. or a naphthyl group optionally substituted with a halogen atom is more preferred, a phenyl group optionally substituted with a halogen atom is still more preferred, and a phenyl group is even more preferred.
- R 52 is preferably a hydrogen atom, an aryl group having 6 to 20 carbon atoms optionally substituted by Z 1 , a hydrogen atom, a phenyl group optionally substituted by Z 1 , or A naphthyl group that may be substituted with Z 1 is more preferred, a phenyl group that may be substituted with Z 1 is even more preferred, and a phenyl group is even more preferred.
- Ar 4 is each independently an aryl group having 6 to 20 carbon atoms. It is an aryl group having 6 to 20 carbon atoms which may be substituted with a certain diarylamino group. Specific examples of the aryl group having 6 to 20 carbon atoms are the same as those described above for R 1′ and R 2′ .
- diarylamino group examples include diphenylamino group, 1-naphthylphenylamino group, di(1-naphthyl)amino group, 1-naphthyl-2-naphthylamino group, di(2-naphthyl)amino group and the like. mentioned.
- Ar 4 includes phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, p-( diphenylamino)phenyl, p-(1-naphthylphenylamino)phenyl, p-(di(1-naphthyl)amino)phenyl group, p-(1-naphthyl-2-naphthylamino)phenyl, p-[di(2 -Naphthyl)amino]phenyl group and the like are preferable, and p-(diphenylamino)phenyl group is more preferable.
- each Ar 2 is independently a group represented by any one of formulas (Ar2-1) to (Ar2-18), particularly formulas (Ar2-1'-1) to (Ar2-1'-1) to ( A group represented by any one of Ar2-18'-2) is preferred.
- Ar 4 has the same meaning as above, DPA is a diphenylamino group, and broken lines are bonds.
- R 155 is a hydrogen atom, and an aryl group having 6 to 14 carbon atoms optionally substituted by Z 1 , or a heteroaryl group having 2 to 14 carbon atoms which may be substituted with Z 1 .
- the aryl group and heteroaryl group the same groups as described in the description of R 1′ and R 2′ can be mentioned.
- R 155 is a hydrogen atom, a phenyl group optionally substituted with Z 1 , a 1-naphthyl group optionally substituted with Z 1 , a 2-naphthyl group optionally substituted with Z 1 a 2-pyridyl group optionally substituted by Z 1 , a 3-pyridyl group optionally substituted by a phenyl group optionally substituted by Z 1 , or a 4 optionally substituted by Z 1
- a -pyridyl group is preferred, a phenyl group optionally substituted by Z 1 is more preferred, and a phenyl group or a (2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl) group is even more preferred. .
- R 156 and R 157 are optionally substituted by a phenyl group optionally substituted by Z 1 an aryl group having 6 to 14 carbon atoms, or a heteroaryl group having 2 to 14 carbon atoms optionally substituted by a phenyl group optionally substituted by Z 1 ; Examples of these aryl groups and heteroaryl groups include those described in the description of R 1' and R 2' .
- R 156 and R 157 are preferably an aryl group having 6 to 14 carbon atoms optionally substituted by a phenyl group optionally substituted by Z 1 , optionally substituted by Z 1 a phenyl group optionally substituted by a phenyl group, a 1-naphthyl group optionally substituted by a phenyl group optionally substituted by Z 1 , or a 2-naphthyl group optionally substituted by Z 1 more preferred.
- Ar 3 is a group represented by any one of the formulas (Ar3-1) to (Ar3-8), especially the groups of the formulas (Ar3-1′) to (Ar3-8′) A group represented by either is preferred.
- DPA has the same meaning as above, and the dashed line is a bond.
- p is an integer of 1 to 10, preferably 1 to 5, more preferably 1 to 3, and even more preferably 1 or 2, from the viewpoint of increasing the solubility of the compound in an organic solvent. , 1 is optimal.
- q is 1 or 2.
- the aniline derivative represented by formula (A1) and the aniline derivative represented by formula (A2) can be produced, for example, according to the method described in International Publication No. 2015/050253.
- the tertiary arylamine compound is not limited to those described above as long as it has at least one nitrogen atom and all nitrogen atoms have a tertiary arylamine structure.
- Other tertiary arylamine compounds that can be used in the present invention include, for example, arylamine compounds described in International Publication No. 2005/094133, and triarylamine partial structures and polymerizable compounds described in Japanese Patent No. 5287455. groups, triarylamine compounds described in Japanese Patent No. 5602191, compounds described in paragraph [0054] of Japanese Patent No. 6177771, and the like.
- Preferred examples of the tertiary arylamine compound include, but are not limited to, those shown below.
- Dopant substance is not particularly limited as long as it dissolves in at least one solvent used in the charge-transporting varnish. Either an inorganic dopant substance or an organic dopant substance can be used. . The inorganic and organic dopant substances may be used singly or in combination of two or more. The amount of the dopant substance is appropriately determined in consideration of the type of the dopant substance and the desired degree of charge-transporting properties. ⁇ 100.0.
- a heteropolyacid is preferable as the inorganic dopant substance used in the present invention.
- a heteropolyacid has a structure in which a heteroatom is located at the center of the molecule, typically represented by a Keggin-type chemical structure represented by formula (H1) or a Dawson-type chemical structure represented by formula (H2), It is a polyacid obtained by condensing an isopolyacid, which is an oxyacid such as vanadium (V), molybdenum (Mo), or tungsten (W), with an oxyacid of a different element.
- Oxygen acids of such dissimilar elements mainly include oxyacids of silicon (Si), phosphorus (P), and arsenic (As).
- heteropolyacid examples include phosphomolybdic acid, silicomolybdic acid, phosphotungstic acid, silicotungstic acid, phosphotungstomolybdic acid, etc. These may be used alone or in combination of two or more. good.
- These heteropolyacids are commercially available and can be synthesized by known methods.
- the one type of heteropolyacid is preferably phosphotungstic acid or phosphomolybdic acid, most preferably phosphotungstic acid.
- one of the two or more heteropolyacids is preferably phosphotungstic acid or phosphomolybdic acid, more preferably phosphotungstic acid.
- the heteropolyacid has a large or small number of elements from the structure represented by the general formula, it is obtained as a commercial product, or a known synthesis As long as it is synthesized appropriately according to the method, it can be used in the present invention.
- phosphotungstic acid and phosphomolybdic acid are generally represented by the chemical formula H 3 (PW 12 O 40 ) ⁇ nH 2 O and H 3 (PMo 12 O 40 ) ⁇ nH 2 O, respectively.
- the mass of the heteropolyacid defined in the present invention is not the mass of pure phosphotungstic acid (phosphotungstic acid content) in synthetic products or commercial products, but the commercially available form and known synthesis In a form that can be isolated by the method, it means the total mass in a state containing water of hydration and other impurities.
- the amount of the heteropolyacid used can be about 0.001-50.0, preferably 0.01-20. It is about 0, more preferably about 0.1 to 10.0.
- tetracyanoquinodimethane derivatives and benzoquinone derivatives can be used as organic dopant substances.
- Specific examples of the tetracyanoquinodimethane derivative include 7,7,8,8-tetracyanoquinodimethane (TCNQ) and halotetracyanoquinodimethane represented by formula (H3).
- benzoquinone derivatives include 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), tetrachloro-1,4-benzoquinone (chloranil), trifluoro-1,4- benzoquinone, tetrafluoro-1,4-benzoquinone, tetrabromo-1,4-benzoquinone, tetracyano-1,4-benzoquinone and the like.
- DDQ 2,3-dichloro-5,6-dicyano-1,4-benzoquinone
- chloranil tetrachloro-1,4-benzoquinone
- trifluoro-1,4- benzoquinone tetrafluoro-1,4-benzoquinone
- tetrabromo-1,4-benzoquinone tetracyano-1,4-benzoquinone and the like.
- 2,3-dichloro-5,6-dicyano-p-benzoquinone, trifluorobenzoquinone, tetrafluorobenzoquinone and tetracyanobenzoquinone are preferred, and DDQ, chloranil, tetrafluoro-1,4-benzoquinone and tetracyano-1 ,4-benzoquinone is more preferred, and DDQ is even more preferred.
- R 500 to R 503 each independently represent a hydrogen atom or a halogen atom, and at least one is a halogen atom, preferably at least two are halogen atoms, and at least three are halogen atoms. More preferably, all are halogen atoms, and most preferably all are halogen atoms.
- the halogen atom the same ones as described above can be mentioned, but a fluorine atom or a chlorine atom is preferable, and a fluorine atom is more preferable.
- halotetracyanoquinodimethanes include 2-fluoro-7,7,8,8-tetracyanoquinodimethane and 2,5-difluoro-7,7,8,8-tetracyanoquinodimethane.
- F4TCNQ dimethane, tetrafluoro-7,7,8,8-tetracyanoquinodimethane
- F4TCNQ tetrafluoro-7,7,8,8-tetracyanoquinodimethane
- the amount of the tetracyanoquinodimethane derivative and the benzoquinone derivative used is preferably 0.0001 to 100 equivalents, more preferably 0.01 to 50 equivalents, more preferably 0.01 to 50 equivalents, relative to the organic functional materials such as polythiophene derivatives and arylamine derivatives. It is preferably 1 to 20 equivalents.
- arylsulfonic acid compound can also be used as an organic dopant substance.
- arylsulfonic acid compounds include benzenesulfonic acid, tosylic acid, p-styrenesulfonic acid, 2-naphthalenesulfonic acid, 4-hydroxybenzenesulfonic acid, 5-sulfosalicylic acid, p-dodecylbenzenesulfonic acid, and dihexylbenzene.
- arylsulfonic acid compounds examples include arylsulfonic acid compounds represented by formula (H4) or (H5).
- D 1 represents O or S, with O being preferred.
- D 2 represents a naphthalene ring or an anthracene ring, preferably a naphthalene ring.
- D 3 represents a divalent to tetravalent perfluorobiphenyl group, s represents the number of bonds between D 1 and D 3 and is an integer satisfying 2 ⁇ s ⁇ 4, where D 3 is perfluorobiphenyldiyl is preferably a perfluorobiphenyl-4,4'-diyl group and s is 2.
- t represents the number of sulfonic acid groups bonded to D 2 and is an integer that satisfies 1 ⁇ t ⁇ 4, with 2 being optimal.
- D 4 to D 8 each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 20 carbon atoms, a halogenated alkyl group having 1 to 20 carbon atoms, or 2 to 20 carbon atoms. wherein at least three of D 4 to D 8 are halogen atoms.
- halogenated alkyl groups having 1 to 20 carbon atoms include trifluoromethyl, 2,2,2-trifluoroethyl, 1,1,2,2,2-pentafluoroethyl and 3,3,3-trifluoropropyl , 2,2,3,3,3-pentafluoropropyl, 1,1,2,2,3,3,3-heptafluoropropyl, 4,4,4-trifluorobutyl, 3,3,4,4 ,4-pentafluorobutyl, 2,2,3,3,4,4,4-heptafluorobutyl, 1,1,2,2,3,3,4,4,4-nonafluorobutyl groups and the like. be done.
- Halogenated alkenyl groups having 2 to 20 carbon atoms include perfluorovinyl, perfluoropropenyl (perfluoroallyl), perfluorobutenyl groups and the like.
- Other examples of the halogen atom and the alkyl group having 1 to 20 carbon atoms are the same as those mentioned above, but the halogen atom is preferably a fluorine atom.
- D 4 to D 8 are a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, or a a halogenated alkenyl group
- at least three of D 4 to D 8 are preferably fluorine atoms, hydrogen atom, fluorine atom, cyano group, nitro group, alkyl group having 1 to 5 carbon atoms, More preferably, it is a fluorinated alkyl group having 1 to 5 carbon atoms or a fluorinated alkenyl group having 2 to 5 carbon atoms
- at least three of D 4 to D 8 are fluorine atoms, a hydrogen atom, a fluorine atom, a cyano group, a nitro group, a perfluoroalkyl group having 1 to 5 carbon atoms, or a perfluoroalken
- the perfluoroalkyl group is a group in which all hydrogen atoms of an alkyl group are substituted with fluorine atoms
- the perfluoroalkenyl group is a group in which all hydrogen atoms of an alkenyl group are substituted with fluorine atoms.
- u represents the number of sulfonic acid groups bonded to the naphthalene ring and is an integer that satisfies 1 ⁇ u ⁇ 4, preferably 2 to 4, and most preferably 2.
- Suitable arylsulfonic acid compounds are listed below, but are not limited to these.
- the amount of the arylsulfonic acid compound used is preferably about 0.01 to 20.0, more preferably about 0.4, in terms of the amount (mol) ratio of the organic functional material such as polythiophene derivatives and arylamine derivatives. ⁇ 5.0.
- Commercially available arylsulfonic acid compounds may be used, but they can also be synthesized by known methods described in International Publication No. 2006/025342, International Publication No. 2009/096352, and the like.
- the dopant substance functions as a dopant substance for the first time when, for example, part of the molecule is removed by an external stimulus such as heating during baking. It may be a substance that develops or enhances, for example, an arylsulfonic acid ester compound in which the sulfonic acid group is protected with a group that is easy to leave.
- the arylsulfonate ester compound is not particularly limited as long as it has a sulfonate ester group bonded to the aromatic ring.
- the molecular weight of the arylsulfonate compound is preferably 100 or more, more preferably 200 or more, preferably 5,000 or less, more preferably 4,000 or less, and even more preferably It is 3,000 or less, more preferably 2,000 or less.
- the number of sulfonate ester groups in the arylsulfonate ester compound is preferably 2 or more, more preferably 3 or more, and preferably 6 or less, more preferably 5 or less.
- the arylsulfonate compound preferably contains a fluorine-substituted aromatic ring.
- arylsulfonate ester compound examples include the arylsulfonate ester compound disclosed in International Publication No. 2017/217455, the arylsulfonate ester compound disclosed in International Publication No. 2017/217457, and the arylsulfonate ester compound disclosed in International Publication No. 2019/124412. and arylsulfonic acid ester compounds of.
- arylsulfonic acid ester compound those represented by the following formula (B1) or (B1') are preferable.
- a 01 is an optionally substituted m-valent hydrocarbon group having 6 to 20 carbon atoms and containing one or more aromatic rings, or the following formula ( B1a) or an m-valent group derived from the compound represented by (B1b) (that is, obtained by removing m hydrogen atoms on the aromatic ring of the compound represented by the following formula (B1a) or (B1b)) group).
- W 1 and W 2 are each independently —O—, —S—, —S(O)— or —S(O 2 )—, or optionally substituted —N -, -Si-, -P- or -P(O)-.
- the m-valent hydrocarbon group having 6 to 20 carbon atoms containing one or more aromatic rings is a group obtained by removing m hydrogen atoms from a hydrocarbon having 6 to 20 carbon atoms containing one or more aromatic rings.
- Hydrocarbons containing one or more aromatic rings include benzene, toluene, xylene, biphenyl, naphthalene, anthracene, pyrene, and the like.
- the m-valent hydrocarbon group is preferably a group derived from benzene, biphenyl or the like.
- Some or all of the hydrogen atoms in the above hydrocarbon group may be further substituted with a substituent.
- the substituents include halogen atoms (fluorine, chlorine, bromine, and iodine atoms), nitro, cyano, hydroxy, amino, silanol, thiol, carboxy, sulfonate, phosphoric acid, phosphate, ester, and thioester. , amide, monovalent hydrocarbon, organooxy, organoamino, organosilyl, organothio, acyl, and sulfo groups.
- the monovalent hydrocarbon group may be linear, branched or cyclic, and specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, Alkyl groups having 1 to 10 carbon atoms such as tert-butyl, n-pentyl, cyclopentyl, n-hexyl, cyclohexyl, n-heptyl, n-octyl, n-nonyl and n-decyl groups; vinyl, 1-propenyl, 2 -Alkenyl groups having 2 to 10 carbon atoms such as propenyl, isopropenyl, 1-methyl-2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl and hexenyl groups; phenyl, xylyl, tolyl, 1-naphthyl, aryl groups having
- organooxy groups include alkoxy, alkenyloxy, and aryloxy groups.
- alkyl group, alkenyl group and aryl group contained in these groups are the same as those described above.
- organoamino groups include methylamino, ethylamino, propylamino, butylamino, pentylamino, hexylamino, cyclohexylamino, heptylamino, octylamino, nonylamino, decylamino and dodecylamino groups having 1 to 1 carbon atoms.
- alkylamino groups dimethylamino, diethylamino, dipropylamino, dibutylamino, dipentylamino, dihexylamino, dicyclohexylamino, diheptylamino, dioctylamino, dinonylamino, didecylamino groups, etc. each alkyl group having 1 to 12 carbon atoms;
- a dialkylamino group which is an alkyl group; a morpholino group, and the like.
- organosilyl group examples include trimethylsilyl, triethylsilyl, tripropylsilyl, tributylsilyl, tripentylsilyl, trihexylsilyl, pentyldimethylsilyl, hexyldimethylsilyl, octyldimethylsilyl, and decyldimethylsilyl groups.
- a trialkylsilyl group in which the group is an alkyl group having 1 to 10 carbon atoms can be mentioned.
- organothio groups include alkylthio groups having 1 to 12 carbon atoms such as methylthio, ethylthio, propylthio, butylthio, pentylthio, hexylthio, heptylthio, octylthio, nonylthio, decylthio and dodecylthio groups.
- alkylthio groups having 1 to 12 carbon atoms such as methylthio, ethylthio, propylthio, butylthio, pentylthio, hexylthio, heptylthio, octylthio, nonylthio, decylthio and dodecylthio groups.
- acyl group include acyl groups having 1 to 10 carbon atoms such as formyl, acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl and be
- the number of carbon atoms in these monovalent hydrocarbon groups, organooxy groups, organoamino groups, organosilyl groups, organothio groups and acyl groups is preferably 1 to 8.
- a fluorine atom, a sulfonic acid group, an alkyl group, an organooxy group, and an organosilyl group are more preferable.
- a 02 is -O-, -S- or -NH-. Of these, -O- is preferred because it is easy to synthesize.
- a 03 is an (n+1)-valent aromatic group having 6 to 20 carbon atoms.
- the (n+1)-valent aromatic group is a group obtained by removing (n+1) hydrogen atoms on the aromatic ring from an aromatic compound having 6 to 20 carbon atoms.
- aromatic compounds mean aromatic hydrocarbons and aromatic heterocyclic compounds. Examples of the aromatic compounds include benzene, toluene, xylene, biphenyl, naphthalene, anthracene, and pyrene. Among these , the aromatic group represented by A3 includes groups derived from naphthalene or anthracene. is preferred.
- X 1 is an alkylene group having 2 to 5 carbon atoms, and this alkylene group has —O—, — An S- or carbonyl group may intervene, and some or all of the hydrogen atoms may be further substituted with an alkyl group having 1 to 20 carbon atoms.
- X 1 is preferably an ethylene, trimethylene, methyleneoxymethylene, methylenethiomethylene group or the like, and some or all of the hydrogen atoms in these groups may be further substituted with an alkyl group having 1 to 20 carbon atoms.
- the alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, cyclopentyl, n-hexyl, cyclohexyl, n-heptyl, n-octyl, Examples include n-nonyl, n-decyl, n-undecyl, n-dodecyl and bicyclohexyl groups.
- X 2 is a single bond, -O-, -S- or NR-.
- R is a hydrogen atom or a monovalent hydrocarbon group having 1 to 10 carbon atoms.
- Preferred monovalent hydrocarbon groups are alkyl groups such as methyl, ethyl and n-propyl groups.
- X 2 is preferably a single bond, -O- or -S-, more preferably a single bond or -O-.
- X 3 is an optionally substituted monovalent hydrocarbon group having 1 to 20 carbon atoms.
- This monovalent hydrocarbon group may be linear, branched or cyclic, and specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl and tert-butyl.
- n-pentyl cyclopentyl, n-hexyl, cyclohexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, bicyclohexyl and other alkyl groups having 1 to 20 carbon atoms alkenyl groups having 2 to 20 carbon atoms such as vinyl, 1-propenyl, 2-propenyl, isopropenyl, 1-methyl-2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl and hexenyl groups; phenyl, xylyl , tolyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenan
- X 3 is preferably an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms.
- m is an integer that satisfies 1 ⁇ m ⁇ 4, but is preferably 2.
- n is an integer that satisfies 1 ⁇ n ⁇ 4, preferably 2.
- the aryl sulfonate ester compounds represented by formulas (B1) and (B1′) exhibit high solubility in a wide range of solvents including low-polarity solvents, so that the physical properties of solutions can be evaluated using a wide variety of solvents. It can be prepared and has high application properties. Therefore, it is preferable to apply the sulfonic acid ester and generate sulfonic acid when the coating film is dried or baked.
- the temperature at which sulfonic acid is generated from the sulfonic acid ester is preferably stable at room temperature and is preferably equal to or lower than the firing temperature. Furthermore, considering high stability in the varnish and ease of desorption during firing, the temperature is preferably 80 to 230°C, more preferably 120 to 180°C.
- arylsulfonic acid ester compound represented by formula (B1) those represented by any one of the following formulas (B1-1) to (B1-3) are preferable.
- a 11 is an m-valent group derived from perfluorobiphenyl (that is, a group obtained by removing m fluorine atoms from perfluorobiphenyl).
- a 12 is -O- or -S-, but -O- is preferred.
- a 13 is an (n+1)-valent group derived from naphthalene or anthracene (that is, a group obtained by removing (n+1) hydrogen atoms from naphthalene or anthracene), preferably a group derived from naphthalene. .
- R s1 to R s4 are each independently a hydrogen atom or a linear or branched alkyl group having 1 to 6 carbon atoms, and R s5 may be substituted. It is a good monovalent hydrocarbon group having 2 to 20 carbon atoms.
- linear or branched C 1-6 alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl and n-hexyl groups. etc. Among these, alkyl groups having 1 to 3 carbon atoms are preferred.
- the monovalent hydrocarbon group having 2 to 20 carbon atoms may be linear, branched or cyclic, and specific examples thereof include ethyl, n-propyl, isopropyl, n-butyl, isobutyl and sec-butyl. , an alkyl group such as a tert-butyl group; and an aryl group such as a phenyl, naphthyl and phenanthryl group.
- R s1 to R s4 it is preferred that R s1 or R s3 is a linear alkyl group having 1 to 3 carbon atoms and the rest are hydrogen atoms. Furthermore, it is preferable that R s1 is a linear alkyl group having 1 to 3 carbon atoms and R s2 to R s4 are hydrogen atoms. A methyl group is preferable as the straight-chain alkyl group having 1 to 3 carbon atoms.
- R s5 is preferably a linear alkyl group having 2 to 4 carbon atoms or a phenyl group.
- m is an integer that satisfies 1 ⁇ m ⁇ 4, but is preferably 2.
- n is an integer that satisfies 1 ⁇ n ⁇ 4, preferably 2.
- a 14 is an optionally substituted m-valent hydrocarbon group having 6 to 20 carbon atoms and containing one or more aromatic rings.
- An m-valent hydrocarbon group is a group obtained by removing m hydrogen atoms from a hydrocarbon having 6 to 20 carbon atoms and containing one or more aromatic rings.
- Hydrocarbons include benzene, toluene, xylene, ethylbenzene, biphenyl, naphthalene, anthracene, phenanthrene, and the like.
- hydrogen atoms in the above hydrocarbon group may be further substituted with substituents, and such substituents include halogen atoms (fluorine atom, chlorine atom, bromine atom, iodine atom, atom), nitro, cyano, hydroxy, amino, silanol, thiol, carboxy, sulfonate, phosphoric acid, phosphate, ester, thioester, amide, monovalent hydrocarbon, organooxy, organoamino, organosilyl, organothio, acyl, sulfo group and the like.
- a 14 is preferably a group derived from benzene, biphenyl or the like.
- a 15 is —O— or —S—, but —O— is preferred.
- a 16 is an (n+1)-valent aromatic hydrocarbon group having 6 to 20 carbon atoms.
- the (n+1)-valent aromatic hydrocarbon group is a group obtained by removing (n+1) hydrogen atoms from the aromatic ring of an aromatic hydrocarbon compound having 6 to 20 carbon atoms.
- aromatic hydrocarbon compounds include benzene, toluene, xylene, biphenyl, naphthalene, anthracene, and pyrene.
- a 16 is preferably a group derived from naphthalene or anthracene, more preferably a group derived from naphthalene.
- R s6 and R s7 are each independently a hydrogen atom or a linear or branched monovalent aliphatic hydrocarbon group.
- R s8 is a linear or branched monovalent aliphatic hydrocarbon group.
- the total number of carbon atoms of R s6 , R s7 and R s8 is 6 or more.
- the upper limit of the total number of carbon atoms in R s6 , R s7 and R s8 is not particularly limited, it is preferably 20 or less, more preferably 10 or less.
- linear or branched monovalent aliphatic hydrocarbon groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-hexyl, n - Alkyl groups having 1 to 20 carbon atoms such as octyl, 2-ethylhexyl and decyl; vinyl, 1-propenyl, 2-propenyl, isopropenyl, 1-methyl-2-propenyl, 1-butenyl, 2-butenyl, 3 -Alkenyl groups having 2 to 20 carbon atoms such as butenyl and hexenyl groups.
- R s6 is preferably a hydrogen atom
- R s7 and R s8 are preferably alkyl groups having 1 to 6 carbon atoms. In this case, R s7 and R s8 may be the same or different.
- m is an integer that satisfies 1 ⁇ m ⁇ 4, but is preferably 2.
- n is an integer that satisfies 1 ⁇ n ⁇ 4, preferably 2.
- R s9 to R s13 are each independently a hydrogen atom, a nitro group, a cyano group, a halogen atom, an alkyl group having 1 to 10 carbon atoms, or a halogenated alkyl group having 1 to 10 carbon atoms. , or a halogenated alkenyl group having 2 to 10 carbon atoms.
- the alkyl group having 1 to 10 carbon atoms may be linear, branched or cyclic, and specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, cyclopentyl, n-hexyl, cyclohexyl, n-heptyl, n-octyl, n-nonyl, n-decyl groups and the like.
- the halogenated alkyl group having 1 to 10 carbon atoms is not particularly limited as long as it is a group in which some or all of the hydrogen atoms of the alkyl group having 1 to 10 carbon atoms have been substituted with halogen atoms.
- the halogenated alkyl group may be linear, branched or cyclic, and specific examples thereof include trifluoromethyl, 2,2,2-trifluoroethyl, 1,1,2,2,2-penta fluoroethyl, 3,3,3-trifluoropropyl, 2,2,3,3,3-pentafluoropropyl, 1,1,2,2,3,3,3-heptafluoropropyl, 4,4,4 -trifluorobutyl, 3,3,4,4,4-pentafluorobutyl, 2,2,3,3,4,4,4-heptafluorobutyl, 1,1,2,2,3,3,4 , 4,4-nonafluorobutyl group and the like.
- the halogenated alkenyl group having 2 to 10 carbon atoms is not particularly limited as long as it is a group in which some or all of the hydrogen atoms of the alkenyl group having 2 to 10 carbon atoms are substituted with halogen atoms.
- Specific examples include perfluorovinyl, perfluoro-1-propenyl, perfluoro-2-propenyl, perfluoro-1-butenyl, perfluoro-2-butenyl, and perfluoro-3-butenyl groups.
- R s9 is preferably a nitro group, a cyano group, a halogenated alkyl group having 1 to 10 carbon atoms, a halogenated alkenyl group having 2 to 10 carbon atoms, and the like.
- a halogenated alkyl group of 4, a halogenated alkenyl group having 2 to 4 carbon atoms, and the like are more preferable, and a nitro group, a cyano group, a trifluoromethyl group, a perfluoropropenyl group, and the like are even more preferable.
- R s10 to R s13 are preferably halogen atoms, more preferably fluorine atoms.
- a 17 is -O-, -S- or -NH-, but -O- is preferred.
- a 18 is an (n+1)-valent aromatic hydrocarbon group having 6 to 20 carbon atoms.
- the (n+1)-valent aromatic hydrocarbon group is a group obtained by removing (n+1) hydrogen atoms from the aromatic ring of an aromatic hydrocarbon compound having 6 to 20 carbon atoms.
- the aromatic hydrocarbon compounds include benzene, toluene, xylene, biphenyl, naphthalene, anthracene, and pyrene.
- a 18 is preferably a group derived from naphthalene or anthracene, more preferably a group derived from naphthalene.
- R s14 to R s17 are each independently a hydrogen atom or a linear or branched monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms.
- the monovalent aliphatic hydrocarbon group may be linear, branched, or cyclic, and specific examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert -C1-C20 alkyl groups such as butyl, n-pentyl, cyclopentyl, n-hexyl, cyclohexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl and n-dodecyl groups; Examples thereof include alkenyl groups having 2 to 20 carbon atoms such as vinyl, 1-propenyl, 2-propenyl, iso
- R s18 is a linear or branched monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, or OR s19 .
- R s19 is an optionally substituted monovalent hydrocarbon group having 2 to 20 carbon atoms.
- R s18 is a monovalent aliphatic hydrocarbon group
- R s18 is preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, and an alkyl group having 1 to 8 carbon atoms. is even more preferred.
- Examples of monovalent hydrocarbon groups having 2 to 20 carbon atoms represented by R s19 include, among the monovalent aliphatic hydrocarbon groups described above, those other than methyl groups, and aryl groups such as phenyl, naphthyl, and phenanthryl groups. etc. Among these, R s19 is preferably a linear alkyl group having 2 to 4 carbon atoms or a phenyl group.
- the substituent which the above monovalent hydrocarbon group may have includes a fluorine atom, an alkoxy group having 1 to 4 carbon atoms, a nitro group, a cyano group, and the like.
- n is an integer that satisfies 1 ⁇ n ⁇ 4, but is preferably 2.
- arylsulfonic acid ester compound represented by formula (B1-3) those represented by the following formula (B1-3-1) or (B1-3-2) are particularly preferable.
- R s20 is a linear or branched monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, and specific examples thereof are the same as those mentioned in the explanation of R s18 .
- R s14 to R s17 is a linear alkyl group having 1 to 3 carbon atoms, and the rest are hydrogen. Atoms are preferred. Furthermore, it is preferable that R s14 is a linear alkyl group having 1 to 3 carbon atoms and R s15 to R s17 are hydrogen atoms. A methyl group is preferable as the linear alkyl group having 1 to 3 carbon atoms. R s19 is preferably a linear alkyl group having 2 to 4 carbon atoms or a phenyl group.
- the total number of carbon atoms of R s14 , R s16 and R s20 is preferably 6 or more.
- the upper limit of the total number of carbon atoms in R s14 , R s16 and R s20 is preferably 20 or less, more preferably 10 or less.
- R s14 is preferably a hydrogen atom
- R s16 and R s20 are preferably C 1-6 alkyl groups.
- R s16 and R s20 may be the same or different.
- the arylsulfonate compound represented by formula (B1) may be used alone or in combination of two or more.
- Suitable arylsulfonate ester compounds include, but are not limited to, those shown below.
- the amount of the arylsulfonic acid ester compound used is preferably about 0.01 to 20.0, more preferably about 0.01 to 20.0 times the organic functional material 1, such as polythiophene derivatives and arylamine derivatives, in terms of substance amount (mol) ratio. It is about 05-15.
- the molecular weight of organic dopants such as arylsulfonic acid compounds and arylsulfonic acid ester compounds is not particularly limited, but considering the solubility in organic solvents when used together with charge-transporting substances, it is preferably 4000. Below, more preferably 3000 or less, and still more preferably 2000 or less.
- solvent used in preparing the charge-transporting varnish of the present invention a highly polar solvent capable of satisfactorily dissolving the charge-transporting substance used can be used. Also, if desired, less polar solvents may be used because they are more process compatible than highly polar solvents.
- a low polarity solvent is defined as having a dielectric constant of less than 7 at a frequency of 100 kHz, and a high polarity solvent is defined as having a dielectric constant of 7 or more at a frequency of 100 kHz.
- low-polarity solvents examples include Chlorinated solvents such as chloroform and chlorobenzene; aromatic hydrocarbon solvents such as toluene, xylene, tetralin, cyclohexylbenzene, decylbenzene; Aliphatic alcohol solvents such as 1-octanol, 1-nonanol, 1-decanol; Ether solvents such as tetrahydrofuran, dioxane, anisole, 4-methoxytoluene, 3-phenoxytoluene, dibenzyl ether, diethylene glycol dimethyl ether, diethylene glycol butyl methyl ether, triethylene glycol dimethyl ether, triethylene glycol butyl methyl ether; Esters such as methyl benzoate, ethyl benzoate, butyl benzoate, isoamyl benzoate, bis(2-ethylhexyl) phthalate, dibutyl maleate, dibutyl o
- Amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N,N-dimethylisobutyramide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone; Ketone solvents such as ethyl methyl ketone, isophorone, cyclohexanone; Cyano solvents such as acetonitrile and 3-methoxypropionitrile; Polyhydric alcohol solvents such as ethylene glycol, diethylene glycol, triethylene glycol, dipropylene glycol, 1,3-butanediol, 2,3-butanediol; Other than aliphatic alcohols such as diethylene glycol monomethyl ether, diethylene glycol monophenyl ether, triethylene glycol monomethyl ether, dipropylene glycol monomethyl ether, benzyl alcohol, 2-phenoxyethanol, 2-benzyloxyethanol, 3-phenoxy
- the above charge-transporting varnish is used for the purpose of improving the injection property to the hole transporting layer and improving the life characteristics of the device. It may contain an organic silane compound. Its content is usually about 1 to 30% by mass with respect to the total mass of the charge-transporting substance and the dopant substance.
- the viscosity of the charge-transporting varnish is determined appropriately according to the thickness of the thin film to be prepared and the solid content concentration, but is usually 1 to 50 mPa ⁇ s at 25°C. is.
- the solid content means components other than the solvent contained in the charge-transporting varnish.
- the solid content concentration of the charge-transporting varnish is appropriately determined in consideration of the viscosity and surface tension of the varnish, the thickness of the thin film to be produced, etc., but is usually 0.1 to 10.0 mass. %, preferably about 0.5 to 5.0% by mass, more preferably about 1.0 to 3.0% by mass, in consideration of improving the coatability of the varnish.
- the method for preparing the charge-transporting varnish is not particularly limited.
- a charge-transporting substance and a dopant substance are dissolved in a highly polar solvent, and then a low-polarity solvent and surface-treated metal oxide nanoparticles are added thereto. or a method of mixing a high-polarity solvent and a low-polarity solvent, dissolving the charge-transporting substance and the dopant substance therein, and then adding the surface-treated metal oxide nanoparticles.
- the charge-transporting varnish described above can be used to easily produce a charge-transporting thin film, it can be suitably used in the production of electronic devices, particularly organic EL devices.
- the charge-transporting thin film can be formed by coating the above-described charge-transporting varnish on the base material and baking it.
- the method of applying the varnish is not particularly limited, and includes dipping, spin coating, transfer printing, roll coating, brush coating, inkjet, spraying, slit coating, and the like. It is preferable to adjust the viscosity and surface tension of the varnish accordingly.
- the firing atmosphere of the charge-transporting varnish after application is not particularly limited. However, depending on the type of dopant substance used, a thin film having charge-transporting properties may be obtained with good reproducibility by baking the varnish in an air atmosphere.
- the firing temperature is appropriately determined within a range of about 100 to 260° C. in consideration of the use of the obtained thin film, the degree of charge transport property to be imparted to the obtained thin film, the type and boiling point of the solvent, etc.
- the obtained thin film is is used as a hole injection layer of an organic EL device, the temperature is preferably about 140 to 250°C, more preferably about 145 to 240°C.
- a thin film with good charge transport properties can also be obtained by calcination. It should be noted that, during the firing, the temperature may be changed in two or more stages for the purpose of expressing a higher uniform film-forming property or promoting the reaction on the substrate. Suitable equipment such as an oven may be used.
- the thickness of the charge-transporting thin film is not particularly limited, but when it is used as a functional layer provided between the anode and the light-emitting layer, such as a hole injection layer, a hole transport layer, and a hole injection transport layer of an organic EL device. , 5 to 300 nm.
- a method for changing the film thickness there are methods such as changing the solid content concentration in the varnish and changing the amount of the solution on the substrate during coating.
- the charge-transporting thin film of the present invention described above exhibits an average transmittance of 90% or more in a wavelength range of 400 to 800 nm at a film thickness of 50 nm, and in one embodiment, an average transmittance of 92% or more. In some embodiments, it exhibits an average transmittance of 95% or more.
- the charge-transporting thin film When the charge-transporting thin film is applied to an organic EL device, the charge-transporting thin film may be provided between a pair of electrodes constituting the organic EL device.
- Typical structures of the organic EL element include (a) to (f) below, but are not limited to these.
- an electron blocking layer or the like may be provided between the light emitting layer and the anode, and a hole blocking layer or the like may be provided between the light emitting layer and the cathode, if necessary.
- the hole injection layer, the hole transport layer or the hole injection transport layer may also function as an electron blocking layer or the like, and the electron injection layer, the electron transport layer or the electron injection transport layer may contain holes (holes).
- anode/hole-injection layer/hole-transport layer/light-emitting layer/electron-transport layer/electron-injection layer/cathode (b) anode/hole-injection layer/hole-transport layer/light-emitting layer/electron-injection-transport layer/ Cathode (c) anode/hole injection transport layer/light emitting layer/electron transport layer/electron injection layer/cathode (d) anode/hole injection transport layer/light emitting layer/electron injection transport layer/cathode (e) anode/positive Hole-injection layer/hole-transport layer/light-emitting layer/cathode (f) Anode/hole-injection-transport layer/light-emitting layer/cathode
- Hole injection layer is layers formed between a light-emitting layer and an anode that transport holes from the anode to the light-emitting layer.
- a hole-transporting material is provided between the light-emitting layer and the anode, it is a "hole-injection-transport layer", and between the light-emitting layer and the anode,
- the layer close to the anode is the “hole-injecting layer” and the other layer is the “hole-transporting layer”.
- the hole-injecting (transporting) layer is a thin film that is excellent not only in the ability to accept holes from the anode but also in the ability to inject holes into the hole-transporting (light-emitting) layer.
- Electrode injection layer is layers formed between a light-emitting layer and a cathode, and have the function of transporting electrons from the cathode to the light-emitting layer.
- a “light-emitting layer” is an organic layer having a light-emitting function, and includes a host material and a dopant material when a doping system is employed.
- the host material mainly promotes recombination of electrons and holes and has the function of confining excitons in the light-emitting layer, and the dopant material efficiently emits the excitons obtained by recombination. have a function.
- the host material mainly functions to confine excitons generated by the dopant within the light-emitting layer.
- the charge-transporting thin film of the present invention can be used as a functional layer provided between an anode and a light-emitting layer in an organic EL device, and is suitable as a hole-injecting layer, a hole-transporting layer, and a hole-injecting-transporting layer. , more suitable as a hole injection layer or a hole transport layer, and even more suitable as a hole injection layer.
- Examples of the materials to be used and the manufacturing method for manufacturing an EL device using the charge-transporting varnish of the present invention include, but are not limited to, the following.
- An example of a method for producing an OLED device having a hole injection layer made of a thin film obtained from the charge-transporting varnish of the present invention is as follows.
- the electrodes are preferably cleaned with alcohol, pure water, or the like, or surface-treated with UV ozone treatment, oxygen-plasma treatment, or the like in advance, as long as the electrodes are not adversely affected.
- a hole injection layer comprising the charge-transporting thin film of the present invention is formed on the anode substrate by the method described above.
- a hole transport layer, a light emitting layer, an electron transport layer, an electron transport layer/hole blocking layer, and a cathode metal are sequentially deposited.
- a composition for forming a hole-transporting layer containing a hole-transporting polymer and a composition for forming a light-emitting layer containing a light-emitting polymer are used. are used to form these layers by a wet process.
- An electron blocking layer may be provided between the light-emitting layer and the hole-transporting layer, if necessary.
- Anode materials include transparent electrodes typified by indium tin oxide (ITO) and indium zinc oxide (IZO), and metal anodes composed of metals typified by aluminum and alloys thereof. It is preferable to have undergone a heat treatment. Polythiophene derivatives and polyaniline derivatives having high charge transport properties can also be used. Other metals constituting the metal anode include gold, silver, copper, indium, and alloys thereof, but are not limited to these.
- Materials for forming the hole transport layer include (triphenylamine) dimer derivatives, [(triphenylamine) dimer] spirodimer, N,N'-bis(naphthalene-1-yl)-N,N'-bis (Phenyl)-benzidine ( ⁇ -NPD), 4,4′,4′′-tris[3-methylphenyl(phenyl)amino]triphenylamine (m-MTDATA), 4,4′,4′′-tris[1 -triarylamines such as naphthyl(phenyl)amino]triphenylamine (1-TNATA), 5,5′′-bis- ⁇ 4-[bis(4-methylphenyl)amino]phenyl ⁇ -2,2′: oligothiophenes such as 5′,2′′-terthiophene (BMA-3T);
- Materials for forming the light-emitting layer include metal complexes such as aluminum complexes of 8-hydroxyquinoline, metal complexes of 10-hydroxybenzo[h]quinoline, bisstyrylbenzene derivatives, bisstyrylarylene derivatives, (2-hydroxyphenyl)benzo Low-molecular light-emitting materials such as thiazole metal complexes and silol derivatives; poly(p-phenylenevinylene), poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylenevinylene], poly(3-alkyl thiophene), polyvinyl carbazole, etc., mixed with a light-emitting material and an electron transfer material, but not limited to these.
- metal complexes such as aluminum complexes of 8-hydroxyquinoline, metal complexes of 10-hydroxybenzo[h]quinoline, bisstyrylbenzene derivatives, bisstyrylarylene derivatives, (2-hydroxyphenyl)benz
- the light-emitting layer when it is formed by vapor deposition, it may be co-deposited with a light - emitting dopant.
- a light - emitting dopant such as rubrene, quinacridone derivatives, condensed polycyclic aromatic rings such as perylene, and the like, but are not limited thereto.
- Materials for forming the electron-transporting layer/hole-blocking layer include, but are not limited to, oxydiazole derivatives, triazole derivatives, phenanthroline derivatives, phenylquinoxaline derivatives, benzimidazole derivatives, pyrimidine derivatives, and the like.
- Materials for forming the electron injection layer include metal oxides such as lithium oxide (Li 2 O), magnesium oxide (MgO), alumina (Al 2 O 3 ), lithium fluoride (LiF), and sodium fluoride (NaF).
- Cathode materials include, but are not limited to, aluminum, magnesium-silver alloys, aluminum-lithium alloys, and the like.
- Materials for forming the electron blocking layer include, but are not limited to, tris(phenylpyrazole) iridium.
- hole-transporting polymers include poly[(9,9-dihexylfluorenyl-2,7-diyl)-co-(N,N'-bis ⁇ p-butylphenyl ⁇ -1,4-diaminophenylene )], poly[(9,9-dioctylfluorenyl-2,7-diyl)-co-(N,N′-bis ⁇ p-butylphenyl ⁇ -1,1′-biphenylene-4,4-diamine )], poly[(9,9-bis ⁇ 1′-penten-5′-yl ⁇ fluorenyl-2,7-diyl)-co-(N,N′-bis ⁇ p-butylphenyl ⁇ -1,4 -diaminophenylene)], poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)-benzidine]-endcapped with polysilsiquinoxane,
- light-emitting polymers examples include polyfluorene derivatives such as poly(9,9-dialkylfluorene) (PDAF), poly(2-methoxy-5-(2′-ethylhexoxy)-1,4-phenylene vinylene) (MEH- PPV) and other polyphenylene vinylene derivatives, poly(3-alkylthiophene) (PAT) and other polythiophene derivatives, and polyvinylcarbazole (PVCz).
- PDAF poly(9,9-dialkylfluorene)
- MEH- PPV poly(2-methoxy-5-(2′-ethylhexoxy)-1,4-phenylene vinylene)
- PAT poly(3-alkylthiophene)
- PVCz polyvinylcarbazole
- the charge-transporting varnish of the present invention is suitable for forming a functional layer provided between an anode and a light-emitting layer, such as a hole-injection layer, a hole-transport layer, and a hole-injection-transport layer of an organic EL element.
- organic photoelectric conversion elements organic thin film solar cells, organic perovskite photoelectric conversion elements, organic integrated circuits, organic field effect transistors, organic thin film transistors, organic light emitting transistors, organic optical inspectors, organic photoreceptors, organic It can also be used to form charge-transporting thin films in electronic devices such as electric field quenching devices, light-emitting electrochemical cells, quantum dot light-emitting diodes, quantum lasers, organic laser diodes and organic plasmon light-emitting devices.
- Measurement of current density of hole-only device Multi-channel IVL measuring device manufactured by EHC Co., Ltd.
- Measurement of transmittance UV-3600 ultraviolet-visible-near-infrared spectrophotometer manufactured by Shimadzu Science Co., Ltd.
- Bromo body 1 (7.71 g, 15.00 mmol, manufactured by YURUI (SHANGHAI) CHEMICAL CO., LTD), Pd(dba) 2 (863.0 mg, 5 mol%, manufactured by Tokyo Chemical Industry Co., Ltd.), (tBu 3 P) 3 HBF 4 (435.0 mg, 5 mol %, manufactured by Kanto Kagaku Co., Ltd.), toluene (120 mL), and LiN(SiMe 3 ) 2 1M toluene solution (33 mL, 33 mmol, manufactured by Aldrich) were added, and the mixture was heated to room temperature. for 20 hours. It was then cooled to 0° C. and treated with 1M HCl aq.
- Preparation Example 2 12 g of a PGMEA dispersion of zirconia particles (PixClear, manufactured by Pixelligent Technologies, average particle size: 7 to 10 nm, zirconia concentration: 50% by mass) and 24 g of triethylene glycol butyl methyl ether were placed in a 300 ml eggplant flask and set on a rotary evaporator. . The mixture was concentrated under reduced pressure until the mass reached 30 g to obtain a triethylene glycol butyl methyl ether-dispersed zirconia sol containing 20% by mass of ZrO 2 .
- the modification amount X (number/nm 2 ) is the specific surface area SA (nm 2 /g), the total amount M (g) of the metal oxide particles, the molecular weight Mw of the silane coupling agent, and the amount Y of the silane coupling agent.
- SA specific surface area
- M total amount of the metal oxide particles
- Mw molecular weight of the silane coupling agent
- Y amount of the silane coupling agent.
- Y X*SA*M*Mw/L.
- the specific gravity of SiO 2 is 2.2 g/cm 3
- the specific gravity of ZrO 2 is 6.0 g/cm 3
- the radius r of the particles used in Preparation Examples 3 and 4 and Comparative Preparation Example 1 is 12 nm.
- the radius r of the particles used in Preparation Examples 5 and 6 was 7 nm.
- Preparation Example 3 5.0 g of methanol-dispersed silica sol (manufactured by Nissan Chemical Industries, Ltd., MT-ST, particle size 10-15 nm, SiO 2 30% by mass, specific gravity 2.2 g/cm 3 ), triethylene glycol butylmethyl are placed in a 50 ml eggplant flask. 10.0 g of ether and 0.2 g of Si1 were added and heated under reflux at 60° C. for 4 hours to modify the silica sol surface with Si1 (calculated modification amount: 0.5 particles/nm 2 ).
- Preparation Example 4 5.0 g of methanol-dispersed silica sol (manufactured by Nissan Chemical Industries, Ltd., MT-ST, particle size 10-15 nm, SiO 2 30% by mass, specific gravity 2.2 g/cm 3 ), triethylene glycol butylmethyl are placed in a 50 ml eggplant flask. 10.0 g of ether and 0.32 g of Si2 were added and heated under reflux at 60° C. for 4 hours to modify the silica sol surface with Si2 (calculated modification amount: 1.0 particles/nm 2 ).
- [Comparative Preparation Example 1] 5.0 g of methanol-dispersed silica sol (manufactured by Nissan Chemical Industries, Ltd., MT-ST, particle size 10-15 nm, SiO 2 30% by mass, specific gravity 2.2 g/cm 3 ), triethylene glycol butylmethyl are placed in a 50 ml eggplant flask. 10.0 g of ether and 0.66 g of Si2 were added and heated under reflux at 60° C. for 4 hours to modify the silica sol surface with Si2 (calculated modification amount: 2.0 particles/nm 2 ). However, sedimentation of particles was confirmed several hours after the reaction, and a modified silica sol could not be obtained.
- Example 1-2 In a nitrogen atmosphere, 0.034 g of arylamine compound (A1) and 0.091 g of arylsulfonate (D1) were added to 1.67 g of triethylene glycol butyl methyl ether, 1.43 g of butyl benzoate and 0.95 g of dimethyl phthalate. was dissolved in a mixed solvent of 0.83 g of Si2-ST obtained in Preparation Example 4 was added thereto and stirred to obtain a charge-transporting varnish.
- Example 1-3 In a nitrogen atmosphere, 0.068 g of arylamine compound (A1) and 0.18 g of arylsulfonate (D1) were added to 0.93 g of triethylene glycol butyl methyl ether, 1.35 g of butyl benzoate and 0.90 g of dimethyl phthalate. was dissolved in a mixed solvent of 1.57 g of Si1-ST obtained in Preparation Example 3 was added thereto and stirred to obtain a charge-transporting varnish.
- Example 1-4 In a nitrogen atmosphere, 0.068 g of arylamine compound (A1) and 0.18 g of arylsulfonate (D1) were added to 0.83 g of triethylene glycol butyl methyl ether, 1.35 g of butyl benzoate and 0.90 g of dimethyl phthalate. was dissolved in a mixed solvent of 1.67 g of Si2-ST obtained in Preparation Example 4 was added thereto and stirred to obtain a charge-transporting varnish.
- Example 1-5 In a nitrogen atmosphere, 0.048 g of arylamine compound (A1) and 0.127 g of arylsulfonate (D1) were added to 1.98 g of triethylene glycol butyl methyl ether, 1.43 g of butyl benzoate and 0.95 g of dimethyl phthalate. was dissolved in a mixed solvent of 0.47 g of Si1-ZrO2 obtained in Preparation Example 5 was added thereto and stirred to obtain a charge-transporting varnish.
- arylamine compound (A1) and 0.127 g of arylsulfonate (D1) were added to 1.98 g of triethylene glycol butyl methyl ether, 1.43 g of butyl benzoate and 0.95 g of dimethyl phthalate. was dissolved in a mixed solvent of 0.47 g of Si1-ZrO2 obtained in Preparation Example 5 was added thereto and stirred to obtain a charge-transporting varnish.
- Example 1-6 In a nitrogen atmosphere, 0.041 g of arylamine compound (A1) and 0.11 g of arylsulfonate (D1) were added to 1.84 g of triethylene glycol butyl methyl ether, 1.43 g of butyl benzoate and 0.95 g of dimethyl phthalate. was dissolved in a mixed solvent of 0.63 of Si1-ZrO2 obtained in Preparation Example 5 was added thereto and stirred to obtain a charge-transporting varnish.
- Example 1-7 In a nitrogen atmosphere, 0.048 g of arylamine compound (A1) and 0.13 g of arylsulfonate (D1) were added to 2.01 g of triethylene glycol butyl methyl ether, 1.43 g of butyl benzoate and 0.95 g of dimethyl phthalate. was dissolved in a mixed solvent of 0.44 g of Si2--ZrO2 obtained in Preparation Example 6 was added thereto and stirred to obtain a charge-transporting varnish.
- arylamine compound (A1) and 0.13 g of arylsulfonate (D1) were added to 2.01 g of triethylene glycol butyl methyl ether, 1.43 g of butyl benzoate and 0.95 g of dimethyl phthalate. was dissolved in a mixed solvent of 0.44 g of Si2--ZrO2 obtained in Preparation Example 6 was added thereto and stirred to obtain a charge-transporting varnish.
- Example 1-8 In a nitrogen atmosphere, 0.041 g of arylamine compound (A1) and 0.11 g of arylsulfonate (D1) were added to 1.89 g of triethylene glycol butyl methyl ether, 1.43 g of butyl benzoate and 0.95 g of dimethyl phthalate. was dissolved in a mixed solvent of 0.58 g of Si2-ZrO2 obtained in Preparation Example 6 was added thereto and stirred to obtain a charge-transporting varnish.
- Example 2-1 Production of charge-transporting thin film and evaluation of transmittance
- the varnish obtained in Example 1-1 was applied to a quartz substrate using a spin coater, and then dried at 120° C. for 1 minute under air baking. Next, the dried quartz substrate was baked at 230° C. for 15 minutes in an air atmosphere to form a uniform thin film of 50 nm on the quartz substrate.
- Example 2-2 Comparative Example 2-1 and Comparative Example 2-2
- Example 2-1 Same as Example 2-1 except that the varnishes obtained in Example 1-2, Comparative Examples 1-1 and 1-2 were used instead of the varnish obtained in Example 1-1.
- a thin film was formed by the method of
- Example 2-3 The varnish obtained in Example 1-3 was applied to a quartz substrate using a spin coater, and then dried at 120° C. for 1 minute under air baking. Next, the dried quartz substrate was baked at 230° C. for 15 minutes in an air atmosphere to form a uniform thin film of 100 nm on the quartz substrate.
- Example 2-4 Comparative Example 2-3 and Comparative Example 2-4
- Example 2-1 Same as Example 2-1 except that the varnishes obtained in Examples 1-4, Comparative Examples 1-3 and 1-4 were used instead of the varnish obtained in Example 1-3.
- a thin film was formed by the method of
- Examples 2-5 to 2-8, and Comparative Examples 2-5 to 2-6 Examples except that the varnishes obtained in Examples 1-5 to 1-8, Comparative Examples 1-5, and Comparative Examples 1-6 were used instead of the varnishes obtained in Example 1-1.
- a thin film was formed in the same manner as in 2-1.
- the light transmittance was measured with a spectrophotometer using the quartz substrates with thin films obtained in the above examples and comparative examples. The results are shown in FIGS. 1-3 and Tables 1 and 2.
- Example 3-1 Fabrication and property evaluation of hole-only device (HOD)
- the varnish obtained in Example 1-1 was applied to an ITO substrate using a spin coater and then dried at 120° C. for 1 minute in the atmosphere. Next, the dried ITO substrate was baked at 230° C. for 15 minutes in an air atmosphere to form a uniform thin film of 50 nm on the ITO substrate.
- As the ITO substrate a 25 mm ⁇ 25 mm ⁇ 0.7 t glass substrate with a patterned indium tin oxide (ITO) film having a thickness of 150 nm was formed on the surface. , for 30 seconds) to remove impurities on the surface.
- ITO indium tin oxide
- ⁇ -NPD(N,N'-di(1-naphthyl)-N, N'- diphenylbenzidine) was deposited at a rate of 0.2 nm/second to a thickness of 30 nm.
- a hole-only device was produced by forming an aluminum film to a thickness of 80 nm at a rate of 0.2 nm/sec.
- the element was sealed with a sealing substrate, and then its characteristics were evaluated. Sealing was performed by the following procedure.
- the element In a nitrogen atmosphere with an oxygen concentration of 2 ppm or less and a dew point of -76°C or less, the element is placed between the sealing substrates, and the sealing substrates are bonded together with an adhesive (MORESCO Moisture Cut WB90US(P) manufactured by MORESCO Co., Ltd.). rice field. At this time, a water capturing agent (HD-071010W-40 manufactured by Dynic Co., Ltd.) was contained in the sealing substrate together with the element. The bonded sealing substrates were irradiated with UV light (wavelength: 365 nm, irradiation amount: 6,000 mJ/cm 2 ) and then annealed at 80° C. for 1 hour to cure the adhesive.
- UV light wavelength: 365 nm, irradiation amount: 6,000 mJ/cm 2
- Example 3-2 Comparative Example 3-1 and Comparative Example 3-2
- Example 3-1 Same as Example 3-1 except that the varnishes obtained in Example 1-2, Comparative Examples 1-1 and 1-2 were used instead of the varnish obtained in Example 1-1.
- HOD was obtained by the method of
- Example 3-3 A HOD was obtained in the same manner as in Example 3-1, except that the varnish obtained in Example 1-3 was used instead of the varnish obtained in Example 1-1, and the film thickness was 100 nm. .
- Example 3-4 Comparative Example 3-3 and Comparative Example 3-4
- Same as Example 3-3 except that the varnishes obtained in Example 1-4, Comparative Examples 1-3, and Comparative Examples 1-4 were used instead of the varnish obtained in Example 1-1.
- HOD was obtained by the method of
- Example 3- HOD was obtained in the same manner as in 1.
- the thin films prepared from the charge-transporting varnishes of the present invention using silica modified with a silane coupling agent having a conductive functional group show better charge transport than the thin films of the comparative examples. It can be seen that the on the other hand, as shown in Table 4, the thin films produced from the charge-transporting varnishes of the present invention using zirconia modified with a silane coupling agent having a specific conductive functional group, compared to the thin films of the comparative examples, It can be seen that good charge transportability is exhibited.
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Abstract
Description
正孔注入層の形成方法は、蒸着法に代表されるドライプロセスと、スピンコート法に代表されるウェットプロセスとに大別され、これら各プロセスを比べると、ウェットプロセスの方が大面積に平坦性の高い薄膜を効率的に製造できる。それゆえ、有機ELディスプレイの大面積化が進められている現在、ウェットプロセスで形成可能な正孔注入層が望まれており、ウェットプロセスで成膜可能な正孔注入材料に関する技術の報告がなされている(特許文献1)。
この点、本出願人は、電荷輸送性薄膜形成用の組成物中に、シリカやジルコニア等の金属酸化物ナノ粒子を添加することで、高透明な電荷輸送性薄膜が得られることをすでに報告している(特許文献2,3参照)。
1. 電荷輸送性物質と、ドーパント物質と、導電性官能基を有するシランカップリング剤で表面処理された金属酸化物ナノ粒子と、溶媒とを含むことを特徴とする電荷輸送性ワニス、
2. 前記シランカップリング剤が、下記式(S1)で表される化合物である1の電荷輸送性ワニス、
3. 前記Rが、炭素数1~5のアルキル基を表し、A1は、炭素数2~5のアルキレン基を表し、A2は、-O-、-S-、-NH-、アミド結合、またはウレア結合を表し、A3は、フェニルカルバゾール構造を有するアリール基を表す2の電荷輸送性ワニス、
4. 前記シランカップリング剤が、下記式(S1-1)で表される化合物である3の電荷輸送性ワニス、
5. 前記金属酸化物ナノ粒子が、シリカおよびジルコニアから選ばれる少なくとも1種である1~4のいずれかの電荷輸送性ワニス、
6. 前記電荷輸送性物質が、アリールアミン誘導体である1~5のいずれかの電荷輸送性ワニス、
7. 前記ドーパント物質が、アリールスルホン酸化合物である1~6のいずれかの電荷輸送性ワニス、
8. 1~7のいずれかの電荷輸送性ワニスから得られた電荷輸送性薄膜、
9. 8の電荷輸送性薄膜を備える電子素子、
10. 8の電荷輸送性薄膜を備える有機EL素子、
11. 前記電荷輸送性薄膜が、正孔注入層または正孔輸送層である10の有機EL素子
を提供する。
このような特性を有する本発明の電荷輸送性ワニスは、有機EL素子をはじめとする電子素子用薄膜、特に有機ELディスプレイ用薄膜の製造に好適に用いることができる。
本発明に係る電荷輸送性ワニスは、電荷輸送性物質と、ドーパント物質と、導電性官能基を有するシランカップリング剤で表面処理された金属酸化物ナノ粒子(以下、表面処理金属酸化物ナノ粒子という場合もある。)と、溶媒とを含むことを特徴とする。
なお、本発明において、電荷輸送性とは、導電性と同義であり、正孔輸送性と同義である。電荷輸送性ワニスとは、それ自体に電荷輸送性があるものでもよく、それにより得られる固体膜が電荷輸送性を有するものでもよい。
本発明の電荷輸送性ワニスの特徴的な成分である、導電性官能基を有するシランカップリング剤で表面処理された金属酸化物ナノ粒子は、通常、絶縁物である金属酸化物ナノ粒子の表面を、導電性官能基を有するシランカップリング剤で処理することで、電荷輸送性物質との導電パスを形成可能としたものである。
なお、ナノ粒子とは、一次粒子についての平均粒子径がナノメートルのオーダー(典型的には500nm以下)である微粒子を意味する。金属酸化物ナノ粒子とは、ナノ粒子に成形された金属酸化物を意味する。
通常の意味での金属としては、特に限定されるものではないが、スズ(Sn)、チタン(Ti)、アルミニウム(Al)、ジルコニウム(Zr)、亜鉛(Zn)、ニオブ(Nb)、タンタル(Ta)およびW(タングステン)からなる群より選択される1種または2種以上が挙げられる。
一方、半金属とは、化学的および/または物理的性質が金属と非金属の中間である元素を意味する。半金属の普遍的な定義は確立されていないが、本発明では、ホウ素(B)、ケイ素(Si)、ゲルマニウム(Ge)、ヒ素(As)、アンチモン(Sb)およびテルル(Te)の計6元素を半金属とする。これらの半金属は、単独で用いても、2種以上を組み合わせて用いてもよく、また通常の意味での金属と組み合わせて用いてもよい。
A1の炭素数1~10のアルキレン基は、直鎖状、分岐状、環状のいずれでもよく、その具体例としては、メチレン、エチレン、プロピレン、トリメチレン、テトラメチレン、ペンタメチレン、ヘキサメチレン、ヘプタメチレン、オクタメチレン、ノナメチレン、デシレン基等が挙げられるが、これらの中でも、炭素数2~5のアルキレン基が好ましく、炭素数2~4のアルキル基がより好ましく、エチレン基、トリメチレン基がより一層好ましい。
これらの中でも、式(A3-9)および(A3-10)で表さる基が好ましい。
アリーレン基の具体例としては、下記式で示されるものが挙げられるが、これらに限定されるものではない。
また、末端にSH基を有するトリアルコキシシラン化合物と、炭素-炭素二重結合と導電性官能基とを有する化合物とを、公知のエン-チオール反応させて得ることもできる。
さらに、Si-H基を有するトリアルコキシシラン化合物と、炭素-炭素二重結合と導電性官能基とを有する化合物とを、公知のヒドロシリル化反応させて得ることもできる。
また、テトラエトキシシラン等のテトラアルコキシシランとアリール基上に塩素原子、臭素原子等のハロゲン原子とを有する化合物とを公知の条件で反応させて得ることもできる。
これらの化合物は、市販品を用いてもよい。
なお、修飾量X(個/nm2)は、金属酸化物ナノ粒子の粒径(nm)、比重(g/cm3)にて算出した粒子1個の比表面積SA(nm2/g)と、金属酸化物粒子の総量M(g)、シランカップリング材の分子量Mw、シランカップリング材の量Y(g)、アボガドロ定数Lを用い、Y=X*SA*M*Mw/Lにて、算出される値である。
分散媒としては、例えば、水、メタノール、メチルエチルケトン、メチルイソブチルケトン、N,N-ジメチルアセトアミド、エチレングリコール、イソプロパノール、メタノール、エチレングリコールモノプロピルエーテル、シクロヘキサノン、酢酸エチル、トルエン、プロピレングリコールモノメチルエーテルアセタート等が挙げられる。
用いるゾルの量は、最終的にワニスに含まれる表面処理金属酸化物ナノ粒子の量が、上述の金属酸化物ナノ粒子の配合量となるように、その濃度を考慮して適宜決定される。
電荷輸送性物質としては、特に限定されるものではなく、例えば、有機ELの分野等で用いられる電荷輸送性化合物、電荷輸送性オリゴマー、電荷輸送性ポリマー等から適宜選択して用いることができる。
その具体例としては、オリゴアニリン誘導体、N,N’-ジアリールベンジジン誘導体、N,N,N’,N’-テトラアリールベンジジン誘導体等のアリールアミン誘導体;オリゴチオフェン誘導体、チエノチオフェン誘導体、チエノベンゾチオフェン誘導体等のチオフェン誘導体;オリゴピロール等のピロール誘導体などの各種電荷輸送性化合物や、電荷輸送性オリゴマー、ポリチオフェン誘導体、ポリアニリン誘導体、ポリピロール誘導体等の電荷輸送性ポリマー等が挙げられ、これらの中でも、ポリチオフェン誘導体、アリールアミン誘導体が好ましい。
炭素数1~20のアルキル基は、直鎖状、分岐状、環状のいずれでもよく、その具体例としては、メチル、エチル、n-プロピル、イソプロピル、n-ブチル、イソブチル、sec-ブチル、tert-ブチル、n-ペンチル、n-ヘキシル、n-ヘプチル、n-オクチル、n-ノニル、n-デシル基等の炭素数1~20の直鎖状または分岐状アルキル基;シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、シクロヘプチル、シクロオクチル、シクロノニル、シクロデシル、ビシクロブチル、ビシクロペンチル、ビシクロヘキシル、ビシクロヘプチル、ビシクロオクチル、ビシクロノニル、ビシクロデシル基等の炭素数3~20の環状アルキル基等が挙げられる。
炭素数2~20のヘテロアリール基としては、2-チエニル、3-チエニル、2-フラニル、3-フラニル、2-オキサゾリル、4-オキサゾリル、5-オキサゾリル、3-イソオキサゾリル、4-イソオキサゾリル、5-イソオキサゾリル、2-チアゾリル、4-チアゾリル、5-チアゾリル、3-イソチアゾリル、4-イソチアゾリル、5-イソチアゾリル、2-イミダゾリル、4-イミダゾリル、2-ピリジル、3-ピリジル、4-ピリジル基等が挙げられる。
ドーパント物質としては、電荷輸送性ワニスに使用する少なくとも1種の溶媒に溶解するものであれば特に限定されず、無機系のドーパント物質、有機系のドーパント物質のいずれも使用できる。無機系および有機系のドーパント物質は、1種類単独で用いてもよく、2種類以上組み合わせて用いてもよい。
ドーパント物質の量は、その種類や所望の電荷輸送性の程度等を勘案して適宜決定されるため一概に規定できないが、通常、質量比で、の電荷輸送性物質1に対して0.0001~100.0の範囲内である。
ヘテロポリ酸とは、代表的に式(H1)で表されるKeggin型あるいは式(H2)で表されるDawson型の化学構造で示される、ヘテロ原子が分子の中心に位置する構造を有し、バナジウム(V)、モリブデン(Mo)、タングステン(W)等の酸素酸であるイソポリ酸と、異種元素の酸素酸とが縮合してなるポリ酸である。このような異種元素の酸素酸としては、主にケイ素(Si)、リン(P)、ヒ素(As)の酸素酸が挙げられる。
特に、1種類のヘテロポリ酸を用いる場合、その1種類のヘテロポリ酸は、リンタングステン酸またはリンモリブデン酸が好ましく、リンタングステン酸が最適である。また、2種類以上のヘテロポリ酸を用いる場合、その2種類以上のヘテロポリ酸の1つは、リンタングステン酸またはリンモリブデン酸が好ましく、リンタングステン酸がより好ましい。
なお、ヘテロポリ酸は、元素分析等の定量分析において、一般式で示される構造から元素の数が多いもの、または少ないものであっても、それが市販品として入手したもの、あるいは、公知の合成方法にしたがって適切に合成したものである限り、本発明において用いることができる。
すなわち、例えば、一般的には、リンタングステン酸は化学式H3(PW12O40)・nH2Oで、リンモリブデン酸は化学式H3(PMo12O40)・nH2Oでそれぞれ示されるが、定量分析において、この式中のP(リン)、O(酸素)またはW(タングステン)もしくはMo(モリブデン)の数が多いもの、または少ないものであっても、それが市販品として入手したもの、あるいは、公知の合成方法にしたがって適切に合成したものである限り、本発明において用いることができる。この場合、本発明に規定されるヘテロポリ酸の質量とは、合成物や市販品中における純粋なリンタングステン酸の質量(リンタングステン酸含量)ではなく、市販品として入手可能な形態および公知の合成法にて単離可能な形態において、水和水やその他の不純物等を含んだ状態での全質量を意味する。
テトラシアノキノジメタン誘導体の具体例としては、7,7,8,8-テトラシアノキノジメタン(TCNQ)や、式(H3)で表されるハロテトラシアノキノジメタンなどが挙げられる。
また、ベンゾキノン誘導体の具体例としては、2,3-ジクロロ-5,6-ジシアノ-1,4-ベンゾキノン(DDQ)、テトラクロロ-1,4-ベンゾキノン(クロラニル)、トリフルオロ-1,4-ベンゾキノン、テトラフルオロ-1,4-ベンゾキノン、テトラブロモ-1,4-ベンゾキノン、テトラシアノ-1,4-ベンゾキノン等が挙げられる。これらのうち、2,3-ジクロロ-5,6-ジシアノ-p-ベンゾキノン、トリフルオロベンゾキノン、テトラフルオロベンゾキノン、テトラシアノベンゾキノンが好ましく、DDQ、クロラニル、テトラフルオロ-1,4-ベンゾキノン、テトラシアノ-1,4-ベンゾキノンがより好ましく、DDQがより一層好ましい。
ハロゲン原子としては上記と同じものが挙げられるが、フッ素原子または塩素原子が好ましく、フッ素原子がより好ましい。
アリールスルホン酸化合物の具体例としては、ベンゼンスルホン酸、トシル酸、p-スチレンスルホン酸、2-ナフタレンスルホン酸、4-ヒドロキシベンゼンスルホン酸、5-スルホサリチル酸、p-ドデシルベンゼンスルホン酸、ジヘキシルベンゼンスルホン酸、2,5-ジヘキシルベンゼンスルホン酸、ジブチルナフタレンスルホン酸、6,7-ジブチル-2-ナフタレンスルホン酸、ドデシルナフタレンスルホン酸、3-ドデシル-2-ナフタレンスルホン酸、ヘキシルナフタレンスルホン酸、4-ヘキシル-1-ナフタレンスルホン酸、オクチルナフタレンスルホン酸、2-オクチル-1-ナフタレンスルホン酸、ヘキシルナフタレンスルホン酸、7-へキシル-1-ナフタレンスルホン酸、6-ヘキシル-2-ナフタレンスルホン酸、ジノニルナフタレンスルホン酸、2,7-ジノニル-4-ナフタレンスルホン酸、ジノニルナフタレンジスルホン酸、2,7-ジノニル-4,5-ナフタレンジスルホン酸、国際公開第2005/000832号記載の1,4-ベンゾジオキサンジスルホン酸化合物、国際公開第2006/025342号記載のアリールスルホン酸化合物、国際公開第2009/096352号記載のアリールスルホン酸化合物等が挙げられる。
D2は、ナフタレン環またはアントラセン環を表すが、ナフタレン環が好ましい。
D3は、2~4価のパーフルオロビフェニル基を表し、sは、D1とD3との結合数を示し、2≦s≦4を満たす整数であるが、D3がパーフルオロビフェニルジイル基、好ましくはパーフルオロビフェニル-4,4’-ジイル基であり、かつ、sが2であることが好ましい。
tは、D2に結合するスルホン酸基数を表し、1≦t≦4を満たす整数であるが、2が最適である。
その他、ハロゲン原子、炭素数1~20のアルキル基の例としては上記と同様のものが挙げられるが、ハロゲン原子としては、フッ素原子が好ましい。
なお、パーフルオロアルキル基とは、アルキル基の水素原子全てがフッ素原子に置換された基であり、パーフルオロアルケニル基とは、アルケニル基の水素原子全てがフッ素原子に置換された基である。
アリールスルホン酸化合物は市販品を用いてもよいが、国際公開第2006/025342号、国際公開第2009/096352号等に記載の公知の方法で合成することもできる。
アリールスルホン酸エステル化合物としては、下記式(B1)または(B1')で表されるものが好ましい。
上記オルガノチオ基の具体例としては、メチルチオ、エチルチオ、プロピルチオ、ブチルチオ、ペンチルチオ、ヘキシルチオ、ヘプチルチオ、オクチルチオ、ノニルチオ、デシルチオ、ドデシルチオ基等の炭素数1~12のアルキルチオ基が挙げられる。
上記アシル基としては、ホルミル、アセチル、プロピオニル、ブチリル、イソブチリル、バレリル、イソバレリル、ベンゾイル基等の炭素数1~10のアシル基が挙げられる。
上記芳香族化合物としては、ベンゼン、トルエン、キシレン、ビフェニル、ナフタレン、アントラセン、ピレン等が挙げられるが、これらのうち、A3で表される芳香族基としては、ナフタレンまたはアントラセンから誘導される基が好ましい。
X1としては、エチレン、トリメチレン、メチレンオキシメチレン、メチレンチオメチレン基等が好ましく、これらの基の水素原子の一部または全部が、さらに炭素数1~20のアルキル基で置換されていてもよい。このアルキル基としては、メチル、エチル、n-プロピル、イソプロピル、n-ブチル、イソブチル、sec-ブチル、tert-ブチル、n-ペンチル、シクロペンチル、n-ヘキシル、シクロヘキシル、n-ヘプチル、n-オクチル、n-ノニル、n-デシル、n-ウンデシル、n-ドデシル、ビシクロヘキシル基等が挙げられる。
X2としては、単結合、-O-または-S-が好ましく、単結合または-O-がより好ましい。
本発明の電荷輸送性ワニスを調製する際に用いられる溶媒としては、使用する電荷輸送性物質等を良好に溶解し得る高極性溶媒を用いることができる。また、必要に応じて、高極性溶媒よりもプロセス適合性に優れている点で低極性溶媒を用いてもよい。本発明において、低極性溶媒とは周波数100kHzでの比誘電率が7未満のものを、高極性溶媒とは周波数100kHzでの比誘電率が7以上のものと定義する。
クロロホルム、クロロベンゼン等の塩素系溶媒;
トルエン、キシレン、テトラリン、シクロヘキシルベンゼン、デシルベンゼン等の芳香族炭化水素系溶媒;
1-オクタノール、1-ノナノール、1-デカノール等の脂肪族アルコール系溶媒;
テトラヒドロフラン、ジオキサン、アニソール、4-メトキシトルエン、3-フェノキシトルエン、ジベンジルエーテル、ジエチレングリコールジメチルエーテル、ジエチレングリコールブチルメチルエーテル、トリエチレングリコールジメチルエーテル、トリエチレングリコールブチルメチルエーテル等のエーテル系溶媒;
安息香酸メチル、安息香酸エチル、安息香酸ブチル、安息香酸イソアミル、フタル酸ビス(2-エチルヘキシル)、マレイン酸ジブチル、シュウ酸ジブチル、酢酸ヘキシル、ジエチレングリコールモノエチルエーテルアセテート、ジエチレングリコールモノブチルエーテルアセテート等のエステル系溶媒
等が挙げられる。
N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、N,N-ジメチルイソブチルアミド、N-メチルピロリドン、1,3-ジメチル-2-イミダゾリジノン等のアミド系溶媒;
エチルメチルケトン、イソホロン、シクロヘキサノン等のケトン系溶媒;
アセトニトリル、3-メトキシプロピオニトリル等のシアノ系溶媒;
エチレングリコール、ジエチレングリコール、トリエチレングリコール、ジプロピレングリコール、1,3-ブタンジオール、2,3-ブタンジオール等の多価アルコール系溶媒;
ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノフェニルエーテル、トリエチレングリコールモノメチルエーテル、ジプロピレングリコールモノメチルエーテル、ベンジルアルコール、2-フェノキシエタノール、2-ベンジルオキシエタノール、3-フェノキシベンジルアルコール、テトラヒドロフルフリルアルコール等の脂肪族アルコール以外の1価アルコール系溶媒;
ジメチルスルホキシド等のスルホキシド系溶媒
等が挙げられる。
得られる薄膜を有機EL素子の正孔注入層として用いる場合、正孔輸送層への注入性の向上、素子の寿命特性等の改善を目的として、上記電荷輸送性ワニスは、有機シラン化合物を含んでいてもよい。その含有量は、電荷輸送性物質およびドーパント物質の合計質量に対して、通常1~30質量%程度である。
電荷輸送性ワニスの粘度は、作製する薄膜の厚み等や固形分濃度に応じて適宜定まるものではあるが、通常、25℃で1~50mPa・sである。なお、本発明において固形分とは、電荷輸送性ワニスに含まれる溶媒以外の成分を意味する。
また、電荷輸送性ワニスの固形分濃度は、ワニスの粘度および表面張力等や、作製する薄膜の厚み等を勘案して適宜決定されるものではあるが、通常、0.1~10.0質量%程度であり、ワニスの塗布性を向上させることを考慮すると、好ましくは0.5~5.0質量%程度、より好ましくは1.0~3.0質量%程度である。
この場合、電荷輸送性薄膜は、上述した電荷輸送性ワニスを基材上に塗布して焼成して形成することができる。
ワニスの塗布方法としては、特に限定されるものではなく、ディップ法、スピンコート法、転写印刷法、ロールコート法、刷毛塗り、インクジェット法、スプレー法、スリットコート法等が挙げられ、塗布方法に応じてワニスの粘度および表面張力を調節することが好ましい。
なお、焼成の際、より高い均一成膜性を発現させたり、基材上で反応を進行させたりする目的で、2段階以上の温度変化をつけてもよく、加熱は、例えば、ホットプレートやオーブン等、適当な機器を用いて行えばよい。
上記電荷輸送性薄膜を有機EL素子に適用する場合、有機EL素子を構成する一対の電極の間に、上述の電荷輸送性薄膜を備える構成とすることができる。
有機EL素子の代表的な構成としては、以下(a)~(f)が挙げられるが、これらに限定されるわけではない。なお、下記構成において、必要に応じて、発光層と陽極の間に電子ブロック層等を、発光層と陰極の間にホール(正孔)ブロック層等を設けることもできる。また、正孔注入層、正孔輸送層あるいは正孔注入輸送層が電子ブロック層等としての機能を兼ね備えていてもよく、電子注入層、電子輸送層あるいは電子注入輸送層がホール(正孔)ブロック層等としての機能を兼ね備えていてもよい。さらに、必要に応じて各層の間に任意の機能層を設けることも可能である。
(a)陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/電子注入層/陰極
(b)陽極/正孔注入層/正孔輸送層/発光層/電子注入輸送層/陰極
(c)陽極/正孔注入輸送層/発光層/電子輸送層/電子注入層/陰極
(d)陽極/正孔注入輸送層/発光層/電子注入輸送層/陰極
(e)陽極/正孔注入層/正孔輸送層/発光層/陰極
(f)陽極/正孔注入輸送層/発光層/陰極
「電子注入層」、「電子輸送層」および「電子注入輸送層」とは、発光層と陰極との間に形成される層であって、電子を陰極から発光層へ輸送する機能を有するものであり、発光層と陰極の間に、電子輸送性材料の層が1層のみ設けられる場合、それが「電子注入輸送層」であり、発光層と陰極の間に、電子輸送性材料の層が2層以上設けられる場合、陰極に近い層が「電子注入層」であり、それ以外の層が「電子輸送層」である。
「発光層」とは、発光機能を有する有機層であって、ドーピングシステムを採用する場合、ホスト材料とドーパント材料を含んでいる。このとき、ホスト材料は、主に電子と正孔の再結合を促し、励起子を発光層内に閉じ込める機能を有し、ドーパント材料は、再結合で得られた励起子を効率的に発光させる機能を有する。燐光素子の場合、ホスト材料は主にドーパントで生成された励起子を発光層内に閉じ込める機能を有する。
本発明の電荷輸送性ワニスから得られる薄膜からなる正孔注入層を有するOLED素子の作製方法の一例は、以下のとおりである。なお、電極は、電極に悪影響を与えない範囲で、アルコール、純水等による洗浄や、UVオゾン処理、酸素-プラズマ処理等による表面処理を予め行うことが好ましい。
陽極基板上に、上記の方法により、本発明の電荷輸送性薄膜からなる正孔注入層を形成する。これを真空蒸着装置内に導入し、正孔輸送層、発光層、電子輸送層、電子輸送層/ホールブロック層、陰極金属を順次蒸着する。あるいは、当該方法において蒸着で正孔輸送層と発光層を形成する代わりに、正孔輸送性高分子を含む正孔輸送層形成用組成物と発光性高分子を含む発光層形成用組成物を用いてウェットプロセスによってこれらの層を形成する。なお、必要に応じて、発光層と正孔輸送層との間に電子ブロック層を設けてよい。
なお、金属陽極を構成するその他の金属としては、金、銀、銅、インジウムやこれらの合金等が挙げられるが、これらに限定されるわけではない。
また、蒸着で発光層を形成する場合、発光性ドーパントと共蒸着してもよく、発光性ドーパントとしては、トリス(2-フェニルピリジン)イリジウム(III)(Ir(ppy)3)等の金属錯体や、ルブレン等のナフタセン誘導体、キナクリドン誘導体、ペリレン等の縮合多環芳香族環等が挙げられるが、これらに限定されない。
陰極材料としては、アルミニウム、マグネシウム-銀合金、アルミニウム-リチウム合金等が挙げられるが、これらに限定されない。
電子ブロック層を形成する材料としては、トリス(フェニルピラゾール)イリジウム等が挙げられるが、これに限定されない。
(1)基板洗浄:長州産業(株)製 基板洗浄装置(減圧プラズマ方式)
(2)ワニスの塗布:ミカサ(株)製 スピンコーターMS-A100
(3)膜厚測定:(株)小坂研究所製 微細形状測定機サーフコーダET-4000
(4)ホールオンリー素子の作製:長州産業(株)製 多機能蒸着装置システムC-E2L1G1-N
(5)ホールオンリー素子の電流密度の測定:(株)イーエッチシー製 多チャンネルIVL測定装置
(6)透過率の測定:島津サイエンス(株)製 紫外可視近赤外分光光度計UV-3600
[調製例1]
500mlのナスフラスコに、MEK分散シリカゾル(日産化学(株)製、MEK-ST、粒子径10-15nm、SiO230質量%)250gとトリエチレングリコールブチルメチルエーテル170gを入れ、ロータリーエバポレーターにセットした。質量が250gとなるまで減圧濃縮し、SiO230質量%のトリエチレングリコールブチルメチルエーテル分散シリカゾルを得た。
300mlのナスフラスコに、ジルコニア粒子のPGMEA分散液(Pixelligent Technologies社製PixClear、平均粒子径7~10nm、ジルコニア濃度:50質量%)12gとトリエチレングリコールブチルメチルエーテル24gを入れ、ロータリーエバポレーターにセットした。質量が30gとなるまで減圧濃縮し、ZrO220質量%のトリエチレングリコールブチルメチルエーテル分散ジルコニアゾルを得た。
各調製例中の「修飾量計算値」は、次の方法で求めた。
粒子の半径をrとし、粒子の1個当たりの表面積を4πr2から算出し、粒子の1個当たりの体積を4πr3/3から算出した。
算出した粒子の体積とSiO2またはZrO2の比重とを用いて粒子1個当たりの重さを算出た。
算出した粒子1個当たりの重さと粒子1個当たりの表面積から、粒子1個当たりの比表面積を算出した。
そして、修飾量X(個/nm2)を、比表面積SA(nm2/g)と、金属酸化物粒子の総量M(g)、シランカップリング材の分子量Mw、シランカップリング材の量Y(g)およびアボガドロ定数Lを用い、Y=X*SA*M*Mw/Lの式に従い算出した。
なお、SiO2の比重として2.2g/cm3を、ZrO2の比重として6.0g/cm3を用い、調製例3、4および比較調製例1で用いた粒子の半径rは12nmと、調製例5および6で用いた粒子の半径rは7nmとした。
50mlのナスフラスコに、メタノール分散シリカゾル(日産化学(株)製、MT-ST、粒子径10-15nm、SiO230質量%、比重2.2g/cm3)5.0g、トリエチレングリコールブチルメチルエーテル10.0g、Si1 0.2gを入れ、60℃で4時間加熱還流を行い、シリカゾル表面をSi1にて修飾した(修飾量計算値、0.5個/nm2)。反応後、ロータリーエバポレーターにてメタノールを減圧除去し、SiO215.9質量%のトリエチレングリコールブチルメチルエーテル分散Si1修飾シリカゾル(Si1-ST)を得た。
50mlのナスフラスコに、メタノール分散シリカゾル(日産化学(株)製、MT-ST、粒子径10-15nm、SiO230質量%、比重2.2g/cm3)5.0g、トリエチレングリコールブチルメチルエーテル10.0g、Si2 0.32gを入れ、60℃で4時間加熱還流を行い、シリカゾル表面をSi2にて修飾した(修飾量計算値、1.0個/nm2)。反応後、ロータリーエバポレーターにてメタノールを減圧除去し、SiO216.4質量%のトリエチレングリコールブチルメチルエーテル分散Si2修飾シリカゾル(Si2-ST)を得た。
50mlのナスフラスコに、メタノール分散シリカゾル(日産化学(株)製、MT-ST、粒子径10-15nm、SiO230質量%、比重2.2g/cm3)5.0g、トリエチレングリコールブチルメチルエーテル10.0g、Si2 0.66g入れ、60℃で4時間加熱還流を行い、シリカゾル表面をSi2にて修飾した(修飾量計算値、2.0個/nm2)。しかし反応後数時間で粒子の沈降が確認され、修飾シリカゾルを得ることはできなかった。
50mlのナスフラスコに、ジルコニア粒子のPGMEA分散液(Pixelligent Technologies社製PixClear、平均粒子径7~10nm、ジルコニア濃度:50質量%、比重6.0g/cm3)2g、トリエチレングリコールブチルメチルエーテル5.67g、Si1 0.09g入れ、60℃で4時間加熱還流を行い、ジルコニア表面をSi1にて修飾した(修飾量計算値、0.5個/nm2)。反応後、ロータリーエバポレーターにてPGMEAを減圧除去し、SiO215.8質量%のトリエチレングリコールブチルメチルエーテル分散Si1修飾ジルコニアゾル(Si1-ZrO2)を得た。
50mlのナスフラスコに、ジルコニア粒子のPGMEA分散液(Pixelligent Technologies社製PixClear、平均粒子径7~10nm、ジルコニア濃度:50質量%、比重6.0g/cm3)2g、トリエチレングリコールブチルメチルエーテル5.67g、Si1 0.15g入れ、60℃で4時間加熱還流を行い、ジルコニア表面をSi2にて修飾した(修飾量計算値、1個/nm2)。反応後、ロータリーエバポレーターにてPGMEAを減圧除去し、SiO217.1質量%のトリエチレングリコールブチルメチルエーテル分散Si2修飾ジルコニアゾル(Si2-ZrO2)を得た。
[実施例1-1]
窒素雰囲気下で、国際公開第2015/050253号に記載の方法に従って合成した下記アリールアミン化合物(A1)0.034g、国際公開第2017/217455号に記載された方法に従って合成した下記アリールスルホン酸エステル(D1)0.091gを、トリエチレングリコールブチルメチルエーテル1.71g、安息香酸ブチル1.43gおおびフタル酸ジメチル0.95gの混合溶媒に溶解させた。そこへ、調製例3で得られたSi1-ST0.79gを加え撹拌し、電荷輸送性ワニスを得た。
窒素雰囲気下で、アリールアミン化合物(A1)0.034g、アリールスルホン酸エステル(D1)0.091gを、トリエチレングリコールブチルメチルエーテル1.67g、安息香酸ブチル1.43gおよびフタル酸ジメチル0.95gの混合溶媒に溶解させた。そこへ、調製例4で得られたSi2-ST0.83gを加え撹拌し、電荷輸送性ワニスを得た。
窒素雰囲気下で、アリールアミン化合物(A1)0.068g、アリールスルホン酸エステル(D1)0.18gを、トリエチレングリコールブチルメチルエーテル0.93g、安息香酸ブチル1.35gおよびフタル酸ジメチル0.90gの混合溶媒に溶解させた。そこへ、調製例3で得られたSi1-ST1.57gを加え撹拌し、電荷輸送性ワニスを得た。
窒素雰囲気下で、アリールアミン化合物(A1)0.068g、アリールスルホン酸エステル(D1)0.18gを、トリエチレングリコールブチルメチルエーテル0.83g、安息香酸ブチル1.35gおよびフタル酸ジメチル0.90gの混合溶媒に溶解させた。そこへ、調製例4で得られたSi2-ST1.67gを加えて撹拌し、電荷輸送性ワニスを得た。
窒素雰囲気下で、アリールアミン化合物(A1)0.041g、アリールスルホン酸エステル(D1)0.109gを、トリエチレングリコールブチルメチルエーテル1.81g、安息香酸ブチル1.43gおよびフタル酸ジメチル0.95gの混合溶媒に溶解させた。そこへ、調製例1で得られたトリエチレングリコールブチルメチルエーテル分散シリカゾル0.67gを加え撹拌し、電荷輸送性ワニスを得た。
窒素雰囲気下で、アリールアミン化合物(A1)0.034g、アリールスルホン酸エステル(D1)0.091gを、トリエチレングリコールブチルメチルエーテル1.67g、安息香酸ブチル1.43gおよびフタル酸ジメチル0.95gの混合溶媒に溶解させた。そこへ、調製例1で得られたトリエチレングリコールブチルメチルエーテル分散シリカゾル0.83gを加え撹拌し、電荷輸送性ワニスを得た。
窒素雰囲気下で、アリールアミン化合物(A1)0.082g、アリールスルホン酸エステル(D1)0.218gを、トリエチレングリコールブチルメチルエーテル1.12g、安息香酸ブチル1.35gおよびフタル酸ジメチル0.90gの混合溶媒に溶解させた。そこへ、調製例1で得られたトリエチレングリコールブチルメチルエーテル分散シリカゾル1.33gを加え撹拌し、電荷輸送性ワニスを得た。
窒素雰囲気下で、アリールアミン化合物(A1)0.068g、アリールスルホン酸エステル(D1)0.182gを、トリエチレングリコールブチルメチルエーテル0.83g、安息香酸ブチル1.35gおよびフタル酸ジメチル0.90gの混合溶媒に溶解させた。そこへ、調製例1で得られたトリエチレングリコールブチルメチルエーテル分散シリカゾル1.67gを加え撹拌し、電荷輸送性ワニスを得た。
窒素雰囲気下で、アリールアミン化合物(A1)0.048g、アリールスルホン酸エステル(D1)0.127gを、トリエチレングリコールブチルメチルエーテル1.98g、安息香酸ブチル1.43gおよびフタル酸ジメチル0.95gの混合溶媒に溶解させた。そこへ、調製例5で得られたSi1-ZrO2 0.47gを加え撹拌し、電荷輸送性ワニスを得た。
窒素雰囲気下で、アリールアミン化合物(A1)0.041g、アリールスルホン酸エステル(D1)0.11gを、トリエチレングリコールブチルメチルエーテル1.84g、安息香酸ブチル1.43gおよびフタル酸ジメチル0.95gの混合溶媒に溶解させた。そこへ、調製例5で得られたSi1-ZrO2 0.63を加え撹拌し、電荷輸送性ワニスを得た。
窒素雰囲気下で、アリールアミン化合物(A1)0.048g、アリールスルホン酸エステル(D1)0.13gを、トリエチレングリコールブチルメチルエーテル2.01g、安息香酸ブチル1.43gおよびフタル酸ジメチル0.95gの混合溶媒に溶解させた。そこへ、調製例6で得られたSi2-ZrO2 0.44gを加え撹拌し、電荷輸送性ワニスを得た。
窒素雰囲気下で、アリールアミン化合物(A1)0.041g、アリールスルホン酸エステル(D1)0.11gを、トリエチレングリコールブチルメチルエーテル1・89g、安息香酸ブチル1.43gおよびフタル酸ジメチル0.95gの混合溶媒に溶解させた。そこへ、調製例6で得られたSi2-ZrO2 0.58gを加え撹拌し、電荷輸送性ワニスを得た。
窒素雰囲気下で、アリールアミン化合物(A1)0.048g、アリールスルホン酸エステル(D1)0.13gを、トリエチレングリコールブチルメチルエーテル2.08g、安息香酸ブチル1.43gおいよびフタル酸ジメチル0.95gの混合溶媒に溶解させた。そこへ、調製例2で得られたトリエチレングリコールブチルメチルエーテル分散ジルコニアゾル0.37gを加え撹拌し、電荷輸送性ワニスを得た。
窒素雰囲気下で、アリールアミン化合物(A1)0.041g、アリールスルホン酸エステル(D1)0.11gを、トリエチレングリコールブチルメチルエーテル1.98g、安息香酸ブチル1.43gおよびフタル酸ジメチル0.95gの混合溶媒に溶解させた。そこへ、調製例2で得られたトリエチレングリコールブチルメチルエーテル分散ジルコニアゾル0.49gを加え撹拌し、電荷輸送性ワニスを得た。
[実施例2-1]
実施例1-1で得られたワニスを、スピンコーターを用いて石英基板に塗布した後、大気焼成下、120℃で1分間乾燥した。次に、乾燥させた石英基板を大気雰囲気下、230℃で15分間焼成し、石英基板上に50nmの均一な薄膜を形成した。
実施例1-1で得られたワニスの代わりに、実施例1-2、比較例1-1および比較例1-2で得られたワニスをそれぞれ用いた以外は、実施例2-1と同様の方法で、薄膜を形成した。
実施例1-3で得られたワニスを、スピンコーターを用いて石英基板に塗布した後、大気焼成下、120℃で1分間乾燥した。次に、乾燥させた石英基板を大気雰囲気下、230℃で15分間焼成し、石英基板上に100nmの均一な薄膜を形成した。
実施例1-3で得られたワニスの代わりに、実施例1-4、比較例1-3および比較例1-4で得られたワニスをそれぞれ用いた以外は、実施例2-1と同様の方法で、薄膜を形成した。
実施例1-1で得られたワニスの代わりに、実施例1-5~1-8、比較例1-5、および比較例1-6で得られたワニスをそれぞれ用いた以外は、実施例2-1と同様の方法で、薄膜を形成した。
すなわち、シランカップリング材にて修飾したシリカ粒子を含む本発明の電荷輸送性薄膜は、可視領域において優れた透過性を維持できていることが示された。
すなわち、シランカップリング材にて修飾したジルコニア粒子を含む本発明の電荷輸送性薄膜は、可視領域において優れた透過性を維持できていることが示された。
[実施例3-1]
実施例1-1で得られたワニスを、スピンコーターを用いてITO基板に塗布した後、大気下、120℃で1分間乾燥した。次に、乾燥させたITO基板を大気雰囲気下、230℃で15分間焼成し、ITO基板上に50nmの均一な薄膜を形成した。ITO基板としては、パターニングされた厚さ150nmのインジウム錫酸化物(ITO)膜が表面に形成された、25mm×25mm×0.7tのガラス基板を用い、使用前にO2プラズマ洗浄装置(150W、30秒間)によって表面上の不純物を除去した。
次いで、薄膜を形成したITO基板に対し、蒸着装置(真空度1.0×10-5Pa)を用いて、α-NPD(N,N’-ジ(1-ナフチル)-N,N’-ジフェニルベンジジン)を0.2nm/秒にて30nm成膜した。次いで、アルミニウムを0.2nm/秒にて80nm成膜することで、ホールオンリー素子を作製した。
なお、空気中の酸素、水等の影響による特性劣化を防止するため、素子は封止基板により封止した後、その特性を評価した。封止は、以下の手順で行った。酸素濃度2ppm以下、露点-76℃以下の窒素雰囲気中で、素子を封止基板の間に収め、封止基板を接着剤((株)MORESCO製モレスコモイスチャーカットWB90US(P))により貼り合わせた。この際、捕水剤(ダイニック(株)製HD-071010W-40)を素子と共に封止基板内に収めた。貼り合わせた封止基板に対し、UV光を照射(波長:365nm、照射量:6,000mJ/cm2)した後、80℃で1時間、アニーリング処理して接着剤を硬化させた。
実施例1-1で得られたワニスの代わりに、実施例1-2、比較例1-1および比較例1-2で得られたワニスをそれぞれ用いた以外は、実施例3-1と同様の方法でHODを得た。
実施例1-1で得られたワニスの代わりに、実施例1-3で得られたワニスを用い、膜厚を100nmとした以外は、実施例3-1と同様の方法でHODを得た。
実施例1-1で得られたワニスの代わりに、実施例1-4、比較例1-3および比較例1~4で得られたワニスをそれぞれ用いた以外は、実施例3-3と同様の方法でHODを得た。
実施例1-1で得られたワニスの代わりに、実施例1-5~1-8、および比較例1-5~1-6で得られたワニスをそれぞれ用いた以外は、実施例3-1と同様の方法でHODを得た。
一方、表4に示されるように、特定の導電性官能基を有するシランカップリング材に修飾されたジルコニアを用いた本発明の電荷輸送性ワニスから作製した薄膜は、比較例の薄膜に比べ、良好な電荷輸送性を示すことがわかる。
Claims (11)
- 電荷輸送性物質と、ドーパント物質と、導電性官能基を有するシランカップリング剤で表面処理された金属酸化物ナノ粒子と、溶媒とを含むことを特徴とする電荷輸送性ワニス。
- 前記Rが、炭素数1~5のアルキル基を表し、A1は、炭素数2~5のアルキレン基を表し、A2は、-O-、-S-、-NH-、アミド結合、ウレア結合およびこれらの組み合わせを表し、A3は、フェニルカルバゾール構造を有するアリール基を表す請求項2記載の電荷輸送性ワニス。
- 前記金属酸化物ナノ粒子が、シリカおよびジルコニアから選ばれる少なくとも1種である請求項1~4のいずれか1項記載の電荷輸送性ワニス。
- 前記電荷輸送性物質が、アリールアミン誘導体である請求項1~5のいずれか1項記載の電荷輸送性ワニス。
- 前記ドーパント物質が、アリールスルホン酸化合物である請求項1~6のいずれか1項記載の電荷輸送性ワニス。
- 請求項1~7のいずれか1項記載の電荷輸送性ワニスから得られた電荷輸送性薄膜。
- 請求項8記載の電荷輸送性薄膜を備える電子素子。
- 請求項8記載の電荷輸送性薄膜を備える有機エレクトロルミネッセンス素子。
- 前記電荷輸送性薄膜が、正孔注入層または正孔輸送層である請求項10記載の有機エレクトロルミネッセンス素子。
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