WO2007043357A1 - 炭化水素化合物、電荷輸送材料、電荷輸送材料組成物および有機電界発光素子 - Google Patents

炭化水素化合物、電荷輸送材料、電荷輸送材料組成物および有機電界発光素子 Download PDF

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WO2007043357A1
WO2007043357A1 PCT/JP2006/319439 JP2006319439W WO2007043357A1 WO 2007043357 A1 WO2007043357 A1 WO 2007043357A1 JP 2006319439 W JP2006319439 W JP 2006319439W WO 2007043357 A1 WO2007043357 A1 WO 2007043357A1
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group
compound
layer
light emitting
ring
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PCT/JP2006/319439
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English (en)
French (fr)
Japanese (ja)
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Masayoshi Yabe
Misako Okabe
Yuichiro Kawamura
Tomoyuki Ogata
Atsushi Takahashi
Koichiro Iida
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Mitsubishi Chemical Corporation
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Priority to CN2006800346287A priority Critical patent/CN101268029B/zh
Priority to KR1020087008377A priority patent/KR101309502B1/ko
Publication of WO2007043357A1 publication Critical patent/WO2007043357A1/ja

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Definitions

  • Hydrocarbon compound Hydrocarbon compound, charge transport material, charge transport material composition, and organic electroluminescence device
  • the present invention relates to a novel hydrocarbon compound, a charge transport material composed of the hydrocarbon compound, and a charge transport material composition containing the hydrocarbon compound.
  • the present invention also relates to an organic electroluminescent device having high brightness, high efficiency and long life using the hydrocarbon compound.
  • An electroluminescent device using an organic thin film has been developed.
  • An electroluminescent device using an organic thin film that is, an organic electroluminescent device, usually has an anode, a cathode, and an organic layer including at least a luminescent layer provided between these electrodes on a substrate.
  • As the organic layer in addition to the light emitting layer, a hole injection layer, a hole transport layer, a hole blocking layer, an electron transport layer, an electron injection layer, and the like are used. Usually, these layers are stacked to be used as an organic electroluminescent device.
  • organic electroluminescent devices have used fluorescent light emission, but in an attempt to increase the light emission efficiency of the device, it has been studied to use phosphorescent light emission instead of fluorescent light. However, even if phosphorescence is used, sufficient luminous efficiency, luminance and lifetime are not yet obtained.
  • Non-Patent Documents 1 and 2 the following compounds (C-1) and (C-2), which are spherical molecules with excellent dispersibility, are used for thickeners, lubricants, and nanotechnology fields. It has been proposed for use as a molecular weight or molecular standard material, for X-ray beam scattering, etc., and has been attracting attention in various fields because of its excellent heat resistance.
  • Non-Patent Literature l Chem. Mater. 1990, 2, 346-349
  • Non-Patent Document 2 J. Am. Chem. Soc. 1992, 114, 1018—1025
  • the present invention is excellent in heat resistance and light resistance, has good solubility in organic solvents, has high singlet and triplet excitation levels, and has a wide electrical oxidation-reduction.
  • a hydrocarbon compound and a charge transport material having a potential difference are provided.
  • a charge transport material composition comprising the hydrocarbon compound, and an organic electroluminescence device having high luminance, high efficiency and long life using the hydrocarbon compound.
  • the hydrocarbon compound of the present invention is characterized by having a partial structure represented by the following general formula (I) in the molecule.
  • G represents a substituent represented by the following general formula (II)
  • R 2 independently represents an arbitrary hydrocarbon group.
  • the benzene ring to which R 2 and G are bonded has no substituent other than R 1 , R 2 and G.
  • R 3 to R 5 each independently represents a hydrogen atom or an arbitrary hydrocarbon group.
  • the terfel group represented by the formula (II) has no substituent other than R 3 to R 5 ! /.
  • the charge transport material of the present invention is the hydrocarbon compound of the present invention.
  • the charge transport material composition of the present invention contains the hydrocarbon compound of the present invention and a solvent.
  • the organic electroluminescence device of the present invention has a layer containing this hydrocarbon compound in an organic electroluminescence device having an anode, a cathode, and a light emitting layer provided between both electrodes on a substrate. It is characterized by.
  • FIG. 1 is a schematic cross-sectional view showing an example of an organic electroluminescent element of the present invention.
  • FIG. 2 is a schematic cross-sectional view showing another example of the organic electroluminescent element of the present invention.
  • FIG. 3 is a schematic cross-sectional view showing another example of the organic electroluminescent element of the present invention.
  • FIG. 4 is a schematic cross-sectional view showing another example of the organic electroluminescent element of the present invention.
  • FIG. 5 is a schematic cross-sectional view showing another example of the organic electroluminescent element of the present invention.
  • FIG. 6 is a schematic cross-sectional view showing another example of the organic electroluminescent element of the present invention.
  • FIG. 7 is a schematic cross-sectional view showing another example of the organic electroluminescent element of the present invention.
  • FIG. 8 is a schematic cross-sectional view showing another example of the organic electroluminescent element of the present invention.
  • FIG. 9 is a schematic cross-sectional view showing another example of the organic electroluminescent element of the present invention.
  • a hydrocarbon compound having the following specific structure is excellent in heat resistance and light resistance, has good solubility in organic solvents, and has high singlet and triplet properties.
  • this hydrocarbon compound has high efficiency and high efficiency in organic electroluminescent devices, particularly phosphorescent organic electroluminescent devices, having a term excitation level and a wide electric redox potential difference. We have found that long-life devices can be obtained.
  • the present invention has been achieved based on such findings, and the hydrocarbon compound of the present invention is characterized in that it has a partial structure represented by the following general formula (I) in the molecule. To do.
  • the charge transport material of the present invention is characterized by comprising this hydrocarbon compound.
  • the charge transport material composition of the present invention contains this hydrocarbon compound and a solvent.
  • the organic electroluminescent device of the present invention has a layer containing this hydrocarbon compound in an organic electroluminescent device having an anode, a cathode, and a light emitting layer provided between both electrodes on a substrate. It is characterized by.
  • G represents a substituent represented by the following general formula (II)
  • IT independently represents an arbitrary hydrocarbon group.
  • the benzene ring to which RR 2 and G are bonded has no substituent other than RR 2 and G.
  • R 3 to R 5 each independently represents a hydrogen atom or an arbitrary hydrocarbon group.
  • the turfyl group represented by the formula (II) does not have a substituent other than R 3 to R 5 ! /.
  • the hydrocarbon compound of the present invention is excellent in heat resistance and light resistance, has good solubility in organic solvents, has high singlet and triplet excited levels, and has a wide electrical range. Has a redox potential difference.
  • the organic electroluminescence device using the hydrocarbon compound of the present invention has the characteristics as a flat panel display (for example, for OA computers and wall-mounted televisions), an in-vehicle display device, a mobile phone display and a surface light emitter. It can be applied to light sources (eg, light sources for copiers, liquid crystal displays and instrument backlights), display panels, and indicator lights, and their technical value is great.
  • the charge transport material having a hydrocarbon compound power of the present invention and the charge transport material composition containing the hydrocarbon compound have an essentially excellent electrochemical durability. In addition to this, it can also be used effectively for electrophotographic photoreceptors and the like.
  • the compound of the present invention is a hydrocarbon compound, that is, a compound that is powered only by carbon atoms and hydrogen atoms.
  • the hydrocarbon compound of the present invention has a partial structure represented by the general formula (I) in the molecule (hereinafter referred to as “parts”). Sometimes referred to as “Part I”. ).
  • G represents a substituent represented by the following general formula (II), IT independently represents an arbitrary hydrocarbon group.
  • IT independently represents an arbitrary hydrocarbon group.
  • the benzene ring to which R 2 and G are bonded has no substituent other than R 2 and G.
  • R 3 to R 5 each independently represents a hydrogen atom or an arbitrary hydrocarbon group.
  • the turfyl group represented by the formula (II) does not have a substituent other than R 3 to R 5 ! /.
  • a hydrocarbon compound of the present invention in one molecule, the partial structure I have two or more, therefore, there G in the general formula (I), R 1, R 2 is 2 or more, respectively
  • G in the general formula (I) R 1, R 2 is 2 or more, respectively
  • a plurality of G present in one molecule may be the same or different, and a plurality of R 1 and R 2 present in one molecule may be the same or different. Also good.
  • G, R 1 and R 2 may be bonded to each other to form a ring.
  • R 3 to R 5 in the general formula (II) two or more of the partial structures I are present in one molecule, or R 1 and R 2 are represented by the general formula (II). When a plurality of these are present in a molecule due to being a substituent, these may be the same or different.
  • the hydrocarbon compound of the present invention has at least one partial structure (substituent G represented by the above general formula (II)) in which a plurality of phenylene groups are linearly linked at the m-position. , Excellent amorphous High solubility in organic hydrocarbon solvents.
  • -It is more preferable to have two or more partial structures (substituent G represented by the above general formula (II)) in which a plurality of len groups are linearly linked at the m-position. Most preferably.
  • substituent G represented by the above general formula (II)
  • the presence of a benzene ring having a substituent at the 1, 3, 5-position makes it possible to increase the glass without impairing the excellent characteristics as described above. It is possible to have both transition temperatures.
  • ⁇ has one or more p-terphenyl skeletons as partial structures in the molecule. It is more preferable to have two or more.
  • the p-terfel skeleton those represented by the following general formula (IV) are particularly preferred (in the formula (IV), R 6 and R 7 each independently represents a hydrogen atom or an arbitrary hydrocarbon group). To express).
  • R 1 and R 2 each independently represents an arbitrary hydrocarbon group.
  • alkyl group having 1 to 30 carbon atoms for example, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, tert-butyl group, normal hexyl group, cyclohexyl group, octyl group, Decyl group),
  • alkenyl group having 2 to 30 carbon atoms for example, a bur group, a 2,2-dimethylethenyl group, etc.
  • An alkyl group having 2 to 30 carbon atoms eg, an ethur group
  • Aromatic hydrocarbon group having 6 to 30 carbon atoms e.g., benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, perylene ring, tetracene ring, pyrene ring, benzpyrene ring, taricene ring, triphenylene-ring, phenoleanthene ring, etc.
  • an alkyl group having 1 to 30 carbon atoms and an aromatic hydrocarbon group having 6 to 30 carbon atoms and most preferably R 1 and Z or R 2 are represented by the general formula ( ⁇ ). The substituents shown.
  • the substituent may further have an arbitrary number of substituents. Preferred examples of the substituent are the same as those described above.
  • R 3 to R 7 in the general formula (II) each independently represent a hydrogen atom or an arbitrary hydrocarbon group.
  • alkyl group having 1 to 30 carbon atoms for example, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, tert-butyl group, normal hexyl group, cyclohexyl group, octyl group, Decyl group),
  • alkenyl group having 2 to 30 carbon atoms for example, a bur group, a 2,2-dimethylethenyl group, etc.
  • An alkyl group having 2 to 30 carbon atoms (eg, an ethur group),
  • Aromatic hydrocarbon group having 6 to 30 carbon atoms e.g., benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, perylene ring, tetracene ring, pyrene ring, benzpyrene ring, taricene ring, triphenylene-ring, phenoleanthene ring, etc.
  • the above substituent may further have an arbitrary number of substituents. However, the substituent is preferably the same as the specific examples of the substituent.
  • R 3 is particularly preferably a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, or 6 carbon atoms.
  • An aromatic hydrocarbon group having ⁇ 30 most preferably a hydrogen atom or an aromatic hydrocarbon group having 1 to 30 carbon atoms.
  • R 4 is particularly preferably a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, or 6 carbon atoms.
  • R 5 is particularly preferably a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, or 6 carbon atoms.
  • R 6 is particularly preferably a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, or 6 carbon atoms.
  • An aromatic hydrocarbon group having ⁇ 30 most preferably a hydrogen atom or an aromatic hydrocarbon group having 6 to 30 carbon atoms.
  • R 7 is particularly preferably a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, or 6 carbon atoms.
  • An aromatic hydrocarbon group having ⁇ 30 most preferably a hydrogen atom or an aromatic hydrocarbon group having 6 to 30 carbon atoms.
  • the hydrocarbon compound of the present invention is not particularly limited as long as it has one or more partial structures I in one molecule, but the number of partial structures I in one molecule is preferably 1 to : LO range, more preferably in the range of 1-3.
  • the molecular weight of the hydrocarbon compound of the present invention is preferably 5000 or less, more preferably 3000 or less.
  • the molecular weight force of hydrocarbon compounds S If this upper limit is exceeded, it will be difficult to remove impurities, the vaporization temperature will rise, and deposition will become difficult, and It is not preferable because the solubility is lowered and the film formation by the wet method may be hindered.
  • the molecular weight of the hydrocarbon compound is preferably 500 or more, more preferably 600 or more, and particularly preferably 800 or more. If the molecular weight of the hydrocarbon compound is below this lower limit, the heat resistance will be reduced, the practicality will be limited, the vaporization temperature will be lowered, making it difficult to form a film by the vapor deposition method, or in the film formation by a wet method In addition, the film quality may be impaired, which is not preferable.
  • the hydrocarbon compound of the present invention is particularly preferably a compound represented by any one of the following general formulas (III), (IV-1) and (IV-2).
  • R 3 and R 4 have the same meaning as in the above formula (II). Multiple R 3 and R 4 contained in one molecule may be the same or different! /! /.
  • R 3 and R 4 have the same meaning as in formula (II).
  • a plurality of R 3 and R 4 contained in one molecule may be the same or different.
  • R 6 and R 7 each independently represents a hydrogen atom or an arbitrary hydrocarbon group.
  • R 3 and R 4 have the same meanings as in formula (II).
  • R 6 and R 7 each independently represents a hydrogen atom or an arbitrary hydrocarbon group.
  • a plurality of R ′ and R 7 contained in one molecule may be the same or different from each other! /.
  • the hydrocarbon compound of the present invention can be synthesized by a combination of known methods. Specific examples of the synthesis method are shown below.
  • the pre-synthesis step can be omitted.
  • Q is any hydrocarbon group or any leaving group that can be substituted with a hydrocarbon group (for example, iodine, bromine, chlorine, fluorine, trifluoromethane sulfo group, p-toluene sulfo group)
  • ⁇ represents —substituted boron atom such as B (OH) and —B (OR), —
  • MgX group, —ZnX group, —SnX group (where X is iodine, bromine, chlorine, fluorine, etc.
  • Examples of the acid catalyst used in this reaction include titanium tetrachloride, silicon tetrachloride, hydrochloric acid, sulfuric acid, Aluminum chloride, thiol chloride, boron trifluoride 'etherate, sulfuric acid, K
  • Nafion H (see Catalysis Letters, 6 (3-6), 341-344, (1990)), etc., usually 0.1 to LOO moles per mole of acetyl group .
  • the above reaction may be carried out without a solvent, but the solvents used are water, methanol, ethanol, isopropanol, diethylene glycol, toluene, xylene, chlorobenzene, dichlorobenzene, hexane, chloroform.
  • the temperature condition is in the range of ⁇ 20 to 200 ° C., preferably in the range of 0 to 100 ° C.
  • the reaction time is usually about 30 minutes to 48 hours.
  • the atmosphere in the reaction system is air, dry air, nitrogen, argon, etc., preferably dry air, nitrogen, argon.
  • trimethoxymethane or the like can coexist if necessary.
  • Literature related to the above reaction includes:
  • the compound obtained here is an intermediate (ie, corresponding to a Q force)
  • a known bi-aryl group coupling method or a 3-biphenyl group or its group is used.
  • the hydrocarbon compound of the present invention can be obtained.
  • a 3-biphenyl group is obtained by using the above-mentioned known aryl-reel coupling method.
  • the hydrocarbon compound of the present invention can be obtained by introducing the similar group.
  • halogenated aryls are allylboronic acid, allylboronic acid ester, allyl tin chloride, allyl zinc chloride, allyl magnesium bromide, allyl magnesium iodide, etc. 1.5 equivalents) and a zerovalent palladium catalyst such as tetrakis (triphenylphosphine) palladium (0.0001 to 0.2 equivalents relative to X), tert-butoxy sodium, tert-butoxy potassium, cesium carbonate Bases such as hum, sodium carbonate, potassium carbonate, tripotassium phosphate, triethylamine, hydroxy hydroxide, sodium hydroxide, etc.
  • a zerovalent palladium catalyst such as tetrakis (triphenylphosphine) palladium (0.0001 to 0.2 equivalents relative to X), tert-butoxy sodium, tert-butoxy potassium, cesium carbonate
  • Bases such as hum, sodium carbonate, potassium carbonate, trip
  • Methods for purifying compounds include "Separation and purification technology, ND book” (1993, edited by Japan Society of Informatics), “Advanced separation of trace components and difficult-to-purify substances by chemical conversion method” (1988) , Published by IC Co., Ltd.), or the method described in the section “Separation and purification” in “Experimental Chemistry Course (4th edition) 1” (1990, Japan Chemical Society), Known techniques can be used.
  • Product chromatography and purity analysis methods include gas chromatograph (, high-performance liquid chromatograph, high-speed amino acid analyzer, capillary electrophoresis measurement, size exclusion chromatograph (, gel permeation chromatograph (, cross-fractionation chromatograph (mass spectrometry) (,, Nuclear magnetic resonance equipment
  • the hydrocarbon compound of the present invention has high charge transportability, it can be suitably used as an electrophotographic photosensitive member, an organic electroluminescent device, a photoelectric conversion device, an organic solar cell, an organic rectifying device, etc. as a charge transport material.
  • an organic electroluminescent device that has excellent heat resistance and can be stably driven (emitted) for a long period of time can be obtained by using the charge transport material having the power of the hydrocarbon compound of the present invention. Therefore, the hydrocarbon compound and the charge transport material of the present invention are particularly suitable as an organic electroluminescent element material.
  • the charge transport material composition of the present invention contains the above-described hydrocarbon compound of the present invention and a solvent, and is preferably used for an organic electroluminescence device.
  • the solvent contained in the charge transport material composition of the present invention is not particularly limited as long as it is a solvent that dissolves the charge transport material of the present invention as a solute well.
  • aromatic hydrocarbons such as toluene, xylene, methicylene, cyclohexylbenzene, and tetralin
  • halogenated aromatic hydrocarbons such as black benzene, dichlorobenzene, and trichlorobenzene
  • Aromatic ethers such as benzene, nitrite, ru, phenetole, 2-methoxytoluene, 3-methoxytoluene, 4-methoxytoluene, 2,3 dimethylanol, 2,4 dimethylazole, etc .
  • phenol acetate, propion Aromatic esters such as acid phenyl, methyl benzoate, ethyl benzoate, propyl benzoate, n-butyl benzoate
  • Examples of the method for reducing the amount of water in the composition include nitrogen gas sealing, use of a desiccant, dehydration of the solvent in advance, use of a solvent with low water solubility, and the like.
  • a solvent having low water solubility because the solution film can prevent whitening by absorbing moisture in the atmosphere during the wet film-forming process.
  • the charge transport material composition to which the present embodiment is applied has, for example, a water solubility at 25 ° C. of 1% by weight or less, preferably 0.1% by weight or less. It is preferable that the solvent contains 10% by weight or more in the composition.
  • the boiling point of the solvent for the charge transport material composition is preferably 100 ° C or more, preferably It is effective to use a solvent having a boiling point of 150 ° C or higher, more preferably a boiling point of 200 ° C or higher. In order to obtain a more uniform film, it is necessary for the solvent to evaporate from the liquid film immediately after film formation at an appropriate rate.
  • the boiling point is usually 80 ° C or higher, preferably the boiling point is 100 ° C or lower.
  • a solvent having a boiling point of 120 ° C or higher usually a boiling point of less than 270 ° C, preferably a boiling point of less than 250 ° C, more preferably a boiling point of less than 230 ° C.
  • a solvent that satisfies the above-mentioned conditions ie, solute solubility, evaporation rate, and water solubility conditions, may be used alone, but if a solvent that satisfies all the conditions cannot be selected, two or more types of solvents may be used. It is also possible to use a mixture of solvents.
  • the charge transport material composition of the present invention preferably contains a light emitting material.
  • the light emitting material refers to a component that mainly emits light in the charge transport material composition of the present invention, and corresponds to a dopant component in an organic EL device.
  • the amount of light (unit: cdZm 2 ) emitted from the charge transport material composition usually 10 to 100%, preferably 20 to 100%, More preferably 50-: L00%, most preferably 80-: L00% power If identified as luminescence from a component material, it is defined as a luminescent material.
  • any known material can be applied, and a fluorescent light emitting material or a phosphorescent light emitting material can be used singly or in combination, but from the viewpoint of internal quantum efficiency.
  • it is a phosphorescent material.
  • Examples of fluorescent dyes that emit blue light include perylene, pyrene, anthracene, coumarin, P-bis (2-phenylethyl) benzene, and derivatives thereof.
  • Examples of the green fluorescent dye include quinacridone derivatives and coumarin derivatives.
  • Examples of yellow fluorescent dyes include rubrene and perimidone derivatives.
  • Examples of red fluorescent dyes include DCM compounds, benzopyran derivatives, rhodamine derivatives, benzothixanthene derivatives, azabenzothixanthene, and the like.
  • Examples of phosphorescent materials include organometallic complexes containing a metal selected from Group 7 to Group 11 forces in the periodic table.
  • the metal in the phosphorescent organometallic complex containing a metal selected from Group 11 of the periodic table 7 is ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum, gold or the like. Can be mentioned.
  • organometallic complexes compounds represented by the following general formula (V) or the following general formula (VI) are preferable.
  • M represents a metal
  • q represents the valence of the metal
  • L and L ′ represent bidentate ligands.
  • j represents 0, 1 or 2;
  • M d represents a metal
  • T represents carbon or nitrogen
  • R 92 to R 95 each independently represent a substituent. However, when T is nitrogen, there is no R 94 or R 95 .
  • M represents an arbitrary metal, and specific examples of preferable ones include the metals described above as the metals for which the periodic table 7 and 11 group forces are also selected.
  • bidentate ligands L and L ′ in the general formula (V) each represent a ligand having the following partial structure.
  • the ring A1 represents an aromatic hydrocarbon group or an aromatic heterocyclic group, and these may have a substituent.
  • Ring A2 represents a nitrogen-containing aromatic heterocyclic group, and these may have a substituent.
  • substituents include a halogen atom such as a fluorine atom; an alkyl group such as a methyl group or an ethyl group; an alkenyl group such as a vinyl group; a methoxy carbo group.
  • Alkoxy group such as ethoxycarbol group; alkoxy group such as methoxy group and ethoxy group; aryloxy group such as phenoxy group and benzyloxy group; dialkylamino group such as dimethylamino group and jetylamino group; diphenylamino group A diarylamino group such as carbazolyl group; an acyl group such as acetyl group; a haloalkyl group such as trifluoromethyl group; a cyano group; an aromatic hydrocarbon group such as a phenol group, a naphthyl group, and a phenanthyl group.
  • the compound represented by the general formula (V) is more preferably the following general formula (Va), (Vb), (
  • M a represents the same metal as M, and w represents the valence of the metal.
  • Ring A1 may have a substituent and may represent an aromatic hydrocarbon group, and Ring A2 may have a substituent and may have a substituent! / ⁇ represents a nitrogen-containing aromatic heterocyclic group. .
  • M b represents the same metal as M, and w represents the valence of the metal.
  • Ring A1 may have a substituent, may have an aromatic hydrocarbon group or a substituent, and may represent a V ⁇ aromatic heterocyclic group, and ring A2 may have a substituent. Or a nitrogen-containing aromatic heterocyclic group.
  • M e represents the same metal as M, w represents the valence of the metal.
  • J represents 0, 1 or 2;
  • ring A1, ring A1 and ring A1 ′ may each independently have a substituent! / ⁇ ! / ⁇ may have an aromatic hydrocarbon group or substituent! / ⁇ ! ⁇
  • Ring A2 and Ring A2 ′ each independently represent a nitrogen-containing aromatic heterocyclic group which may have a substituent.
  • the group of ring A1 and ring Al ' is preferably, for example, a phenyl group, a biphenyl group, a naphthyl group, or an anthryl group.
  • Chael group, fu Examples include a ryl group, a benzochel group, a benzofuryl group, a pyridyl group, a quinolyl group, an isoquinolyl group, and a carbazolyl group.
  • the group of ring A2 and ring A2 ' is preferably a pyridyl group, pyrimidyl group, pyrazyl group, triazyl group, benzothiazole group, benzoxazole group, benzoimidazole group, quinolyl group, for example. Group, isoquinolyl group, quinoxalyl group, phenanthridyl group and the like.
  • the substituents that the compounds represented by the general formulas (Va), (Vb), (Vc) may have include halogen atoms such as fluorine atoms; methyl groups, ethyl groups, etc.
  • Alkyl groups such as vinyl groups; alkoxy groups such as methoxycarbon groups and ethoxycarbol groups; alkoxy groups such as methoxy groups and ethoxy groups; phenoxy groups and benzyloxy groups
  • a dialkylamino group such as a dimethylamino group or a jetylamino group; a diarylamino group such as a diphenylamino group; a carbazolyl group; an acyl group such as an acetylyl group; a haloalkyl group such as a trifluoromethyl group; a cyano group or the like.
  • halogen atoms such as fluorine atoms
  • Alkyl groups such
  • the carbon number is usually 1 or more and 6 or less. Furthermore, when the substituent is an alkenyl group, the carbon number is usually 2 or more and 6 or less. Further, when the substituent is an alkoxycarbo group, the carbon number is usually 2 or more and 6 or less. Furthermore, when the substituent is an alkoxy group, the carbon number is usually 1 or more and 6 or less. When the substituent is an aryloxy group, the carbon number is usually 6 or more and 14 or less. Further, when the substituent is a dialkylamino group, the carbon number is usually 2 or more and 24 or less.
  • the number of carbon atoms is usually 12 or more and 28 or less.
  • the number of carbon atoms is usually 1 or more and 14 or less.
  • the substituent is a haloalkyl group, the carbon number is usually 1 or more and 12 or less.
  • substituents may be linked to each other to form a ring.
  • substituent of ring A1 and the substituent of ring A2 are bonded, or the substituent of ring A1 ′ and the substituent of ring A2 ′ are bonded,
  • One condensed ring may be formed. Examples of such a condensed ring group include a 7,8-benzoquinoline group.
  • ring Al ring A1 ', ring A2 and ring A2'
  • alkyl preferably alkyl.
  • organometallic complex represented by the general formula (V), (Va), (Vb) or (Vc) are shown below, but are not limited to the following compounds (in the following) Ph represents a full group.
  • the ligands L and Z or L are 2-aryl pyridine ligands, that is, 2-aryl pyridines, those having an arbitrary substituent bonded thereto, and those having an arbitrary group condensed thereto. Preference is given to compounds having.
  • M d represents a metal, and specific examples thereof include the metals described above as metals for which the periodic table group 7 to 11 forces are also selected.
  • metals described above metals for which the periodic table group 7 to 11 forces are also selected.
  • ruthenium, rhodium, noradium, silver, rhenium, osmium, iridium, platinum or gold are preferable, and divalent metals such as platinum and palladium are particularly preferable.
  • R 92 and R 93 are each independently a hydrogen atom, halogen atom, alkyl group, Ararukiru group, an alkenyl group, Shiano group, an amino group, Ashiru group, ⁇ Rukokishikarubo Represents a-group, a carboxyl group, an alkoxy group, an alkylamino group, an aralkylamino group, a haloalkyl group, a hydroxyl group, an aryloxy group, an aromatic hydrocarbon group or an aromatic heterocyclic group.
  • R 94 and R 95 each independently represents a substituent represented by the same exemplary compounds and R 92 and R 93.
  • R 94 and R 95 are absent.
  • R 92 to R 95 may further have a substituent.
  • the substituent which may further have can be any group which is not particularly limited.
  • R 92 to R 95 may be linked to each other to form a ring, and this ring may further have an arbitrary substituent.
  • T-1, T-10 to T-15 of the organometallic complex represented by the general formula (VI) are shown below, but are not limited to the following exemplified compounds.
  • Me represents a methyl group
  • Et represents an ethyl group.
  • organometallic complex the compounds described in WO2005Z019373 can also be used.
  • the charge transport material composition of the present invention may contain various other solvents as required in addition to the solvent and the light emitting material described above.
  • examples of such other solvents include amides such as N, N-dimethylformamide and N, N-dimethylacetamide, and dimethyl sulfoxide.
  • thermosetting resin when two or more layers are laminated by a wet film-forming method, in order to prevent these layers from being compatible with each other, a photo-curable resin is used for the purpose of curing and insolubilizing after film formation, A thermosetting resin can also be contained.
  • the solids concentration of the charge transport material, the luminescent material, and components that can be added as required (leveling agent, etc.) in the charge transport material composition of the present invention is usually 0.01% by weight or more, preferably 0. 05 wt% or more, more preferably 0.1 wt% or more, more preferably 0.5 wt% or more, most preferably 1 wt% or more, usually 80 wt% or less, preferably 50 wt% or less, more It is preferably 40% by weight or less, more preferably 30% by weight or less, and most preferably 20% by weight or less. If this concentration is below the lower limit, it is difficult to form a thick film when forming a thin film, and if it exceeds the upper limit, it is difficult to form a thin film.
  • the weight mixing ratio of the light-emitting material Z charge transport material is usually 0.1 / 99.9 or more, more preferably 0.5 / 99.5. More preferably 1Z99 or more, most preferably 2Z98 or more, usually 50Z50 or less, more preferably 40Z60 or less, still more preferably 30Z70 or less, and most preferably 20Z80 or less. is there. If this ratio falls below the lower limit or exceeds the upper limit, the luminous efficiency may be significantly reduced.
  • the charge transport material composition of the present invention is obtained by dissolving a solute comprising a charge transport material, a light emitting material, and various additives such as a leveling agent and an antifoaming agent that can be added as necessary in an appropriate solvent. It is prepared by. In order to shorten the time required for the dissolution process and to keep the solute concentration in the composition uniform, the solute is usually dissolved while stirring the solution. The dissolution process may be carried out at room temperature! If the dissolution rate is slow, it can be dissolved by heating. After completion of the dissolution process, a filtration process such as filtering may be performed as necessary.
  • An organic electric field generator is formed by forming a layer by a wet film-forming method using the charge transport material composition of the present invention.
  • an optical element When an optical element is produced, if moisture is present in the charge transport material composition used, moisture is mixed into the formed film and the uniformity of the film is impaired. Therefore, the moisture content in the charge transport material composition of the present invention is reduced. The amount is preferably as small as possible.
  • organic electroluminescent elements are often made of materials such as cathodes that deteriorate significantly due to moisture, when moisture is present in the charge transport material composition, moisture remains in the dried film. It is preferable that there is a possibility of deteriorating the characteristics of the element.
  • the amount of water contained in the charge transport material composition of the present invention is usually 1 wt% or less, preferably 0.1 wt% or less, more preferably 0.01 wt% or less. .
  • the charge transport material composition of the present invention is preferably in a uniform liquid state at room temperature in order to improve stability in a wet film-forming process, for example, ejection stability with a nozzle force in an ink-jet film forming method.
  • a uniform liquid at room temperature means that the composition is a liquid composed of a uniform phase and that the composition does not contain a particle component having a particle size of 0.0: Lm or more.
  • the viscosity of the charge transport material composition of the present invention when the viscosity is extremely low, for example, coating surface non-uniformity due to excessive liquid film flow in the film forming process, nozzle ejection failure in ink jet film formation, etc. are likely to occur. When the viscosity is extremely high, nozzle clogging or the like in ink jet film formation tends to occur. Therefore, the viscosity of the composition of the present invention at 25 ° C.
  • mPa ′s or more is usually 2 mPa ′s or more, preferably 3 mPa ′s or more, more preferably 5 mPa ′s or more, and usually 1OOOmPa ′s or less, preferably lOOmPa's or less, more preferably 50 mPa's or less.
  • the surface tension of the charge transport material composition of the present invention is high, the wettability of the liquid for film formation with respect to the substrate is lowered, and the film-forming surface at the time of drying in which the leveling property of the liquid film is poor. Since problems such as turbulence are likely to occur, the surface tension of the composition of the present invention at 20 ° C. is usually less than 50 mNZm, preferably less than 40 mNZm.
  • the vapor pressure of the charge transport material composition of the present invention is high, problems such as changes in the solute concentration due to evaporation of the solvent tend to occur. For this reason, the vapor pressure at 25 ° C. of the composition of the present invention is usually 50 mmHg or less, preferably 10 mmOgHg or less, more preferably lmmHg or less.
  • the charge transport material composition of the present invention is preferably filled in a container capable of preventing the transmission of ultraviolet rays, such as a brown glass bottle, and sealed and stored.
  • the storage temperature is usually ⁇ 30 ° C. or higher, preferably 0 ° C. or higher, and usually 35 ° C. or lower, preferably 25 ° C. or lower.
  • the organic electroluminescent device of the present invention has at least an anode, a cathode, and a light emitting layer provided between both electrodes on a substrate, and has a layer containing the hydrocarbon compound of the present invention.
  • This layer is preferably a layer formed by a wet film-forming method using the charge transport material composition of the present invention, and in particular, this layer is preferably a light emitting layer.
  • the hydrocarbon compound of the present invention is preferably contained in the light emitting layer or the hole blocking layer.
  • FIG. 1 is a substrate
  • 2 is an anode
  • 3 is a hole injection layer
  • 4 is A light emitting layer
  • 5 represents an electron injection layer
  • 6 represents a cathode.
  • the substrate 1 serves as a support for the organic electroluminescent element, and quartz or glass plates, metal plates or metal foils, plastic films or sheets, etc. are used.
  • a glass plate and a transparent synthetic resin plate such as polyester, polymetatalylate, polycarbonate, and polysulfone are preferable.
  • a synthetic resin substrate it is necessary to pay attention to gas barrier properties. If the gas barrier property of the substrate is too small, the organic electroluminescent element may be deteriorated by the outside air that has passed through the substrate, which is not preferable. For this reason, a method of securing a gas noria property by providing a dense silicon oxide film or the like on at least one surface of the synthetic resin substrate is also a preferable method.
  • An anode 2 is provided on the substrate 1.
  • the anode 2 plays a role of hole injection into the layer on the light emitting layer side (such as the hole injection layer 3 or the light emission layer 4).
  • This anode 2 is usually made of metal such as aluminum, gold, silver, nickel, iron ⁇ radium, platinum, metal oxide such as indium and Z or tin, copper iodide, etc. It is composed of a metal halide, carbon black, or a conductive polymer such as poly (3-methylthiophene), polypyrrole or polyaline.
  • the anode 2 is usually formed by a sputtering method, a vacuum deposition method, or the like.
  • an appropriate noinder when forming an anode using fine metal particles such as silver, fine particles such as copper iodide, carbon black, conductive metal oxide fine particles, or conductive polymer fine powder, an appropriate noinder
  • the anode 2 can also be formed by dispersing it in a fat solution and coating it on the substrate 1.
  • a thin film can be formed directly on the substrate 1 by electrolytic polymerization, or the anode 2 can be formed by applying a conductive polymer on the substrate 1 (Appl. Phys. Lett., 60 ⁇ , 2711, 1992).
  • the anode 2 usually has a single-layer structure, but may have a laminated structure having a plurality of material forces if desired.
  • the thickness of the anode 2 varies depending on the required transparency.
  • the visible light transmittance is usually 60% or more, preferably 80% or more.
  • the thickness of the anode is usually 5 nm or more, preferably lOnm or more, and usually lOOOnm or less, preferably about 500 nm or less. If it can be opaque, the thickness of the anode 2 is arbitrary, and the anode 2 may be the same as the substrate 1. Furthermore, it is also possible to laminate different conductive materials on the anode 2 described above.
  • the anode surface is treated with ultraviolet (UV) Z ozone, oxygen plasma, argon plasma. I prefer to handle it.
  • UV ultraviolet
  • the hole injection layer 3 is a layer that transports holes from the anode 2 to the light emitting layer 4, the hole injection layer 3 preferably contains a hole transporting compound.
  • a cationic radical in which one electron is removed from an electrically neutral compound accepts one electron from a nearby electrically neutral compound, whereby a hole is generated.
  • the hole transporting compound gives electrons to the anode 2 when energized, so that the cation of the hole transporting compound A radical is generated, and holes are transported by transferring electrons between the cation radical and an electrically neutral hole transporting compound.
  • the hole injection layer 3 contains a cation radical compound
  • the cation radical necessary for hole transport exists at a concentration higher than that generated by the acid generated by the anode 2, and the positive injection is present.
  • the hole injection layer 3 preferably contains a cation radical compound.
  • an electrically neutral hole transporting compound is present in the vicinity of the cation radical compound, electrons are transferred smoothly, and therefore the cationic radical compound and the hole transporting compound are combined in the hole injection layer 3. More preferably.
  • the cation radical compound is a cation radical that is a chemical species obtained by removing one electron from a hole transport property, a compound force, and an ionic compound that has an anti-ion force.
  • V-holes free carriers
  • the hole injection layer 3 contains a hole transporting compound and an electron accepting compound.
  • the hole injection layer 3 contains a hole transporting compound and an electron accepting compound. It is even more preferable to include. Further, it is more preferable that the hole injection layer 3 contains a cation radical compound and a hole transport compound which preferably contain a cation radical compound.
  • the hole injection layer 3 may contain a binder resin that hardly traps charges or a coating property improving agent, if necessary.
  • the hole injection layer 3 only the electron-accepting compound is formed on the anode 2 by a wet film forming method, and the charge transport material composition of the present invention is directly applied and laminated. Is also possible. In this case, a part of the charge transport material composition of the present invention is an electron accepting compound. By interacting with, a layer having excellent hole injection properties is formed.
  • the hole transporting compound a compound having an ionization potential of 4.5 eV to 6. OeV is preferable.
  • Examples of the hole transporting compound include, in addition to the charge transporting material of the present invention, aromatic amine compounds, phthalocyanine derivatives, porphyrin derivatives, oligothiophene derivatives, and polythiophene derivatives. Of these, aromatic amine compounds are preferable from the viewpoint of amorphousness and visible light transmittance.
  • aromatic tertiary amine compounds such as the charge transport material of the present invention are particularly preferable.
  • the aromatic tertiary amine compound is a compound having an aromatic tertiary amine structure and also includes a compound having a group derived from an aromatic tertiary amine.
  • the type of aromatic tertiary amine compound is not particularly limited, but from the viewpoint of the surface smoothing effect, a polymer compound having a weight average molecular weight of 1000 or more and 1000000 or less (polymerization type carbonization in which repeating units are linked). More preferred are hydrogen compounds).
  • Preferred examples of the aromatic tertiary amine polymer compound include a polymer compound having a repeating unit represented by the following general formula (VII).
  • ⁇ and Ar each independently represent an aromatic hydrocarbon group which may have a substituent, or an aromatic heterocyclic group which may have a substituent.
  • Ar 23 to Ar 25 each independently represents a divalent aromatic hydrocarbon group which may have a substituent, or a divalent aromatic heterocyclic group which may have a substituent.
  • Y represents a linking group selected from the following linking group group.
  • two groups bonded to the same N atom among Ar 21 to Ar 25 may be bonded to each other to form a ring.
  • Ar dl to Ar 41 are each independently 1 derived from an aromatic hydrocarbon ring which may have a substituent or an aromatic heterocyclic ring which may have a substituent. Represents a divalent or divalent group.
  • R 31 and R 32 each independently represents a hydrogen atom or an arbitrary substituent.
  • a monovalent or divalent group derived from any aromatic hydrocarbon ring or aromatic complex ring is applicable. These may be the same or different from each other. Moreover, you may have arbitrary substituents.
  • Examples of the aromatic hydrocarbon ring include a 5- or 6-membered monocyclic ring or a 2-5 condensed ring. Specific examples include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, a tetracene ring, a pyrene ring, a benzpyrene ring, a taricene ring, a triphenylene ring, a acenaphthene ring, a fluoranthene ring, and a fluorene ring.
  • Examples of the aromatic heterocyclic ring include a 5- or 6-membered monocyclic ring or a 2-4 condensed ring. Specific examples include furan ring, benzofuran ring, thiophene ring, benzothiophene ring, pyrrole ring, pyrazole ring, imidazole ring, oxadiazole ring, indole ring, strong rubazole ring, pyrroloimidazole ring, pyrrolopyrazole ring, pyrrolopyrrole ring, chenoviolol.
  • Ar 23 to Ar 25 , Ar 31 to Ar 35 , Ar 37 to Ar 4 are derived from one or more types of aromatic hydrocarbon rings and Z or aromatic heterocycles exemplified above. Two or more divalent groups can be linked and used.
  • aromatic hydrocarbon ring and a Z or an aromatic heterocyclic group derived from Ar 21 to Ar 41 may have a substituent further.
  • the molecular weight of the substituent is usually 400 or less, preferably about 250 or less.
  • the type of the substituent is not particularly limited, and examples thereof include one or more selected from the following substituent group W.
  • a halogen atom such as a fluorine atom or a chlorine atom
  • a haloalkyl group such as a trifluoromethyl group, usually having 1 or more, usually 8 or less, preferably 4 or less
  • a methylthio group or an ethylthio group An alkylthio group having a carbon number of usually 1 or more, usually 10 or less, preferably 6 or less; a phenylthio group, a naphthylthio group, a pyridylthio group, etc.
  • the number of carbon atoms is usually 2 or more, preferably 3 or more, usually 33 or less, preferably 26 or less; such as trimethylsiloxy group or triphenylsiloxy group, and usually has 2 or more carbon atoms, preferably 3 Or more, usually 33 or less, preferably 26 or less siloxy group; cyano group; phenyl group, naphthyl group, etc., aromatic hydrocarbon ring group usually having 6 or more carbon atoms, usually 30 or less, preferably 18 or less; An aromatic heterocyclic group having usually 3 or more, preferably 4 or more, usually 28 or less, preferably 17 or less, such as a group or a pyridyl group.
  • Ar 21 and Ar 22 are monovalent derived from a benzene ring, a naphthalene ring, a phenanthrene ring, a thiophene ring, and a pyridine ring from the viewpoint of the solubility, heat resistance, and hole injection 'transportability of the polymer compound. More preferred are a phenyl group and a naphthyl group.
  • Ar 23 to Ar 25 are divalent groups derived from a benzene ring, a naphthalene ring, an anthracene ring, and a phenanthrene ring from the viewpoint of heat resistance and hole injection and transport properties including redox potential.
  • Preferred are a phenylene group, a biphenylene group, and a naphthylene group.
  • R 31 and R 32 a hydrogen atom or an arbitrary substituent can be applied. These may be the same or different from each other.
  • the type of the substituent is not particularly limited, and examples of applicable substituents include alkyl groups, alkenyl groups, alkyl groups, alkoxy groups, silyl groups, siloxy groups, and aromatic hydrocarbon groups. , Aromatic heterocyclic groups, and halogen atoms. Specific examples thereof include the groups exemplified in the above substituent group W.
  • aromatic tertiary amine polymer compound having a repeating unit represented by the general formula (VII) include those described in WO2005Z089024, and preferred examples thereof are also the same.
  • a compound represented by the structural formula (PB-1) can be mentioned, but is not limited thereto.
  • Preferred examples of other aromatic tertiary amine polymer compounds include, for example, the following general formula (VIII) and
  • Examples thereof include a polymer compound containing a repeating unit represented by Z or general formula (IX).
  • Ar 5 , Ar 47 and Ar 4 ° may each independently have a substituent ⁇ an aromatic hydrocarbon group or a substituent ⁇ Represents an aromatic heterocyclic group.
  • Ar 44 and Ar 46 each independently represents a divalent aromatic hydrocarbon group which may have a substituent, or a divalent aromatic heterocyclic group which may have a substituent.
  • Ar 45 to Ar 48 two groups bonded to the same N atom may be bonded to each other to form a ring.
  • R 41 to R 43 each independently represent a hydrogen atom or an arbitrary substituent.
  • Ar 45 , Ar 47 , Ar 48 and Ar 44 , Ar 46 may include Ar 21 , Same as Ar 22 and Ar 23 to Ar 25 .
  • R 41 to R 43 are preferably a hydrogen atom or a group described in [Substituent group W]. And a hydrogen atom, an alkyl group, an alkoxy group, an amino group, an aromatic hydrocarbon group, and an aromatic hydrocarbon group.
  • aromatic tertiary amine polymer compound containing the repeating unit represented by the general formula (VIII) and Z or (IX) include those described in WO2005Z089024, and preferred examples thereof are also included. A force that is similar is not limited to them.
  • the hole injection layer is formed by a wet film forming method
  • a hole transporting compound that is easily dissolved in various solvents is preferable.
  • the aromatic tertiary amine compound for example, a binaphthyl compound (Japanese Patent Laid-Open No. 2004-014187) and an asymmetric 1,4-phenylenediamine compound (Japanese Patent Laid-Open No. 2004-026732) are preferred.
  • aromatic amine compounds that have been conventionally used as thin film refining materials having hole injection and transport properties in organic electroluminescent devices, compounds that are easily dissolved in various solvents may be appropriately selected. Good.
  • aromatic amine compound applicable to the hole transporting compound of the hole injection layer for example, it has been conventionally used as a layer forming material for hole injection and transporting in organic electroluminescence devices. A well-known compound is mentioned.
  • aromatic diamine compounds in which tertiary aromatic amine units such as 1, 1 bis (4-di-P-triamylaminophenol) cyclohexane are linked JP-A-59-194393
  • 4 , 4'-bis [N- (1-naphthyl) -N-phenolamino] biphenyl, which contains two or more tertiary amines, and two or more condensed aromatic rings are attached to the nitrogen atom.
  • Substituted aromatic amine compounds JP-A-5-234681; derivatives of triphenylbenzene and aromatic triamine compounds having a starburst structure (US Pat. No.
  • N N, —Diphenyl—N, N, —Bis (3-methylphenol) bi-fluoro 4,4, aromatic diamine compounds such as diamine (US Pat. No. 4,764,625); ⁇ , ⁇ , ⁇ ', ⁇ , monotetramethyl ⁇ , ⁇ , monobis (4 di ( ⁇ tolyl) aminophenyl) - ⁇ xylene (Japanese Patent Laid-Open No. 3-2699084); Triphenylamine derivatives that are sterically asymmetric as a whole molecule (Japanese Patent Laid-Open No.
  • phthalocyanine derivative or porphyrin derivative applicable to the hole transporting compound of the hole injection layer include porphyrin, 5, 10, 15, 20-tetraphenyl 21H , 23H Porphyrin, 5, 10, 15, 20—Tetraphenol— 21H, 23H —Porphyrin cobalt (11), 5, 10, 15, 20—Tetraferro-Lu 21H, 23H Porphyrin copper (11), 5, 10 , 15, 20—Tetraphenol—21H, 23H Porphyrin zinc ( ⁇ ), 5, 10, 15, 20—Tetraferroic 21H, 23H Porphyrin vanadium (IV) oxide, 5, 10, 15, 20—Tetra (4 Pyridyl) -21H, 23H porphyrin, 29H, 31H phthalocyanine copper ( ⁇ ), phthalocyanine zinc (11), phthalocyanine titanium, phthalocyanine oxide magnesium, phthalocyanine lead, phthalocyanine copper (11), 4, 4, 4 "
  • oligothiophene derivative applicable as the hole transporting compound of the hole injection layer include ⁇ -terthiophene and its derivatives, ⁇ -sexithiophene and its derivatives, and a naphthalene ring. Examples thereof include oligothiophene derivatives (JP-A-6-256441).
  • polythiophene derivative applicable as the hole transporting compound in the present invention include poly (3,4-ethylenedioxythiophene) (PEDOT), poly (3- Hexylthiophene) and the like.
  • the molecular weight of these hole-transporting compounds is a polymer compound (repeating repeating units). In general, the range is 9000 or less, preferably 5000 or less, and usually 200 or more, preferably 400 or more. If the molecular weight of the hole transporting compound is too high, synthesis and purification are difficult, which is not preferable. On the other hand, if the molecular weight is too low, the heat resistance may be lowered, which is also not preferable.
  • the hole transporting compound used as the material for the hole injection layer may contain one or more of these compounds, and may contain two or more kinds. Also good. When two or more kinds of hole transporting compounds are contained, the combination thereof is arbitrary, but one or more aromatic tertiary amine polymer compounds and one other hole transporting compound are used. Or it is preferable to use 2 or more types together.
  • An electron-accepting compound is preferably a compound having an oxidizing power and the ability to accept one electron from the above-described hole-transporting compound. Specifically, a compound having an electron affinity of 4 eV or more is used. Preferred is a compound that is a compound of 5 eV or more.
  • Examples include 4-isopropyl-1,4'-methyldiphenyl tetrakis (pentafluorophenol) borate and other organic group-substituted onium salts, salted iron (III) ( JP-A-11-251067), high-valence inorganic compounds such as ammonium peroxodisulfate, cyano-compounds such as tetracyanethylene, tris (pentafluorophenyl) borane (JP-A-2003-31365), etc. Aromatic boron compounds, fullerene derivatives, iodine and the like.
  • onium salts substituted with organic groups and high-valent inorganic compounds are soluble in various solvents, and can be applied to wet coating because they have strong acid-like properties.
  • an organic salt-substituted onium salt, a cyan compound, and an aromatic boron compound are preferable.
  • organically substituted onium salts, cyan compounds, and aromatic boron compounds suitable as electron-accepting compounds include those described in WO2005Z089024, and preferred examples thereof. The same applies to, for example, the force including the compound (A-2) represented by the following structural formula, but is not limited thereto.
  • the cation radical compound is a cation radical that is a chemical species obtained by removing one electron from a hole transporting compound, and an ionic compound that also has an anti-ion force.
  • the cation radical when the cation radical is derived from a hole transporting polymer compound, the cation radical has a structure in which one electron of a repeating unit force of the polymer compound is removed.
  • the cation radical is a chemical compound obtained by removing one electron from the above-described compound in the hole transporting compound, and more preferably as a hole transporting compound that is preferably a chemical species. It is more preferable to be a chemical species from the viewpoints of amorphousness, visible light transmittance, heat resistance, and solubility.
  • the cation radical compound can be generated by mixing the hole transport compound and the electron acceptor compound described above. That is, by mixing the aforementioned hole transporting compound and the electron accepting compound, electron transfer occurs from the hole transporting compound to the electron accepting compound, and the cation radical of the hole transporting compound is produced. A cationic ion compound with a counter-on force is generated.
  • Cationic labs derived from polymer compounds such as PEDOT / PSS Advanced Mater., 2000, 12 ⁇ , 481) Jameraldine hydrochloride (J. Phys. Chem., 1990, 94 ⁇ , 7716)
  • Dical compounds are also formed by acid-sodium polymerization (dehydrogenation polymerization), that is, by oxidizing a monomer chemically or electrochemically with peroxysulfate in an acidic solution. To do. In this oxidative polymerization (dehydrogenation polymerization), the monomer is oxidized, resulting in a high content. At the same time, a cation radical is generated, in which one electron is removed from the repeating unit of the polymer, with the ion derived from the acidic solution as a counter ion.
  • the hole injection layer 3 is formed on the anode 2 by a wet film forming method or a vacuum deposition method.
  • ITO indium stannate
  • ITO indium stannate
  • Ra lOnm
  • the defect of the device due to the unevenness of the surface of the anode is generated compared to the case of forming by the vacuum deposition method. Has the advantage of reducing.
  • a predetermined amount of one or more of the above-mentioned materials is added, Do not become a trap of charge if necessary! / ⁇ Binder ⁇
  • a coating improver and dissolve in a solvent to prepare a coating solution, spin coat, spray coat, dip coat, die coat, flexo
  • the positive hole injection layer 3 is formed by applying on the anode by a wet film formation method such as printing, screen printing, or ink jet method, and drying.
  • the solvent used for the layer formation by the wet film forming method the above-mentioned materials (hole transporting compound, electron accepting compound, cation radical compound) can be dissolved. If it is a solvent, the type is not particularly limited, but a deactivating substance that may deactivate each material (hole transporting compound, electron accepting compound, cation radical compound) used for the hole injection layer. Or prefer something that doesn't contain deactivating material.
  • Examples of preferable U and solvent that satisfy these conditions include ether solvents and ester solvents.
  • the ether solvent include aliphatic ethers such as ethylene glycolenoresmethinoleatenore, ethyleneglycololecinoleethenore, propylene glycol 1 monomethyl ether acetate (PGMEA); , 2-dimethoxybenzene, 1,3 dimethoxybenzene, anisole, phenetole, 2-methoxytoluene, 3-methoxytoluene, 4-methoxytoluene, 2,3 dimethylaninol, 2,4 dimethylarsole, etc.
  • ether solvent include aliphatic ethers such as ethylene glycolenoresmethinoleatenore, ethyleneglycololecinoleethenore, propylene glycol 1 monomethyl ether acetate (PGMEA); , 2-dimethoxybenzene, 1,3 dimethoxybenzene, anisole, phenetole
  • ester solvents include aliphatic esters such as ethyl acetate, n-butyl acetate, ethyl acetate, and n-butyl lactate; acetate acetate, propionate, methyl benzoate, ethyl benzoate, And aromatic esters such as propyl benzoate and n-butyl benzoate. Any one of these may be used alone, or two or more may be used in any combination and ratio.
  • Solvents that can be used in addition to the ether solvents and ester solvents described above include, for example, aromatic hydrocarbon solvents such as benzene, toluene, xylene, N, N-dimethylformamide, N, N-dimethyl. Examples include amide solvents such as acetoamide, dimethyl sulfoxide and the like. Any of these may be used alone, or two or more may be used in any combination and ratio. Further, one or more of these solvents may be used in combination with one or more of the ether solvents and ester solvents described above.
  • aromatic hydrocarbon solvents such as benzene, toluene, xylene, N, N-dimethylformamide, N, N-dimethyl.
  • amide solvents such as acetoamide, dimethyl sulfoxide and the like. Any of these may be used alone, or two or more may be used in any combination and ratio. Further, one or more of these solvents may be used in combination with one or more of the
  • aromatic hydrocarbon solvents such as benzene, toluene and xylene have low ability to dissolve electron-accepting compounds and cation radical compounds, so they are mixed with ether solvents and ester solvents. It is preferable to use it.
  • the concentration of the solvent in the coating solution is usually 10% by weight or more, preferably 30% by weight or more, more preferably 50% by weight or more, and usually 99.999% by weight or less, preferably 99.99%. It is not more than wt%, more preferably not more than 99.9 wt%. When two or more solvents are used as a mixture, the total force S of these solvents must satisfy this range.
  • one or more of the above-mentioned materials are placed in a vacuum vessel. Place the crucibles in the crucibles (in case of using more than 2 kinds of materials, put them in each crucible), evacuate the vacuum container to about 10 _4 Pa with a suitable vacuum pump, and then heat the crucibles When using the upper material, heat each crucible) and evaporate by controlling the amount of evaporation (when using two or more materials, evaporate by independently controlling the amount of evaporation) and face the crucible A hole injection layer is formed on the anode of the substrate placed on the substrate. When two or more kinds of materials are used, a mixture of them can be put in a crucible and heated and evaporated to form a hole injection layer.
  • the film thickness of the hole injection layer 3 formed in this way is usually in the range of 5 nm or more, preferably lOnm or more, and usually lOOOnm or less, preferably 500 nm or less.
  • the hole injection layer 3 may be omitted as shown in FIG. [0194]
  • a light emitting layer 4 is usually provided on the hole injection layer 3.
  • the light emitting layer 4 is, for example, a layer containing the above-described light emitting material. Between the electrodes to which an electric field is applied, holes injected from the anode 2 through the hole injection layer 3 and from the cathode 6 through the electron transport layer 5 are used. It is a layer that is excited by recombination with injected electrons and becomes the main light source.
  • the light emitting layer 4 preferably contains a light emitting material (dopant) and one or more host materials, and the light emitting layer 4 more preferably contains the hydrocarbon compound of the present invention as a host material. Force that may be formed by a method It is particularly preferable that the layer be formed by a wet film-forming method using the charge transport material composition of the present invention.
  • the wet film forming method is a method in which a composition containing a solvent as described above is formed by spin coating, spray coating, dip coating, die coating, flexographic printing, screen printing, an ink jet method, or the like. is there.
  • the light emitting layer 4 may contain other materials and components as long as the performance of the present invention is not impaired. Further, the light emitting layer 4 may have a two-layer structure or a multi-layer structure having three or more layers. In this case, the composition ratio of each layer may be different, or it may contain different materials. Also good. It is also possible to provide a charge generation layer having a force such as vanadium pentoxide between the layers.
  • the organic layer such as the hole injection layer 3 and the electron transport layer 5 described later is provided in addition to the light emitting layer 4, the light emitting layer 4, the hole injection layer 3, the electron transport layer 5, etc.
  • the total film thickness combined with other organic layers is usually 30 nm or more, preferably 50 nm or more, more preferably lOOnm or more, usually lOOOnm or less, preferably 500 nm or less, more preferably 300 nm or less.
  • the conductivity of the hole injection layer 3 other than the light emitting layer 4 or the electron injection layer 5 described later is high, the amount of charge injected into the light emitting layer 4 increases. It is also possible to reduce the drive voltage while maintaining the total film thickness to some extent by increasing the film thickness of layer 3 and decreasing the film thickness of light emitting layer 4.
  • the thickness of the light emitting layer 4 is usually lOnm or more, preferably 20 nm or more, and usually 300 ⁇ m or less, preferably 200 nm or less.
  • the film thickness of the light emitting layer 4 is usually 30 nm or more, preferably 50 nm or more, usually 500 nm or less, preferably 300 nm or less. It is.
  • the electron injection layer 5 serves to efficiently inject electrons injected from the cathode 6 into the light emitting layer 4.
  • the material for forming the electron injection layer 5 is an alkali metal such as sodium or cesium, which is preferable for a metal having a low work function, or an alkaline earth metal such as norium or calcium.
  • the film thickness of the electron injection layer 5 is preferably 0.1 to 5 nm.
  • a cathode buffer layer 10 such as LiF, MgF, Li 0, Cs CO, etc. as shown in FIGS. 8 and 9 is formed at the interface between the cathode 6 and the light emitting layer 4 or the electron transport layer 8 described later. l ⁇ 5nm about)
  • organic electron transport materials represented by metal complexes such as nitrogen-containing heterocyclic compounds such as bathophenantorin described later and aluminum complexes of 8-hydroxyquinoline include sodium, potassium, cesium, lithium, rubidium. And the like (as described in JP-A-10-270171, JP-A-2002-100478, JP-A-2002-100482, etc.) to improve electron injection / transport properties and excellent film quality This is preferable because it is possible to achieve both.
  • the film thickness is usually 5 nm or more, preferably lOnm or more, usually 200 nm or less, preferably lOOnm or less.
  • the electron injection layer 5 is formed by laminating on the light emitting layer 4 by a wet film forming method or a vacuum deposition method in the same manner as the light emitting layer 4.
  • the evaporation source is placed in a crucible or metal boat installed in a vacuum vessel, the inside of the vacuum vessel is evacuated to about 10 _4 Pa with an appropriate vacuum pump, and then the crucible or metal boat is heated. Evaporate and rub An electron injection layer is formed on a substrate placed opposite to the metal boat or the metal boat.
  • the alkali metal is vapor-deposited using an Al metal dispenser in which nichrome is filled with an alkali metal chromate and a reducing agent. By heating the dispenser in a vacuum container, the alkali metal chromate is reduced and the alkali metal is evaporated.
  • an organic electron transport material and an alkali metal place the organic electron transport material in a crucible installed in a vacuum vessel and evacuate the vacuum vessel to about 10 _4 Pa with a suitable vacuum pump. Each crucible and dispenser are simultaneously heated and evaporated to form an electron injection layer on the substrate placed facing the crucible and dispenser.
  • the co-evaporation is uniformly performed in the film thickness direction of the electron injection layer 5, but there may be V and concentration distribution in the film thickness direction! /.
  • the electron injection layer 5 may be omitted as shown in FIGS.
  • the cathode 6 serves to inject electrons into a layer on the light emitting layer side (such as the electron injection layer 5 or the light emitting layer 4).
  • the material used for the cathode 6 can be the material used for the anode 2, but a metal having a low work function is preferred for efficient electron injection.
  • Tin, magnesium, indium, calcium A suitable metal such as aluminum, silver, or an alloy thereof is used.
  • Specific examples include low work function alloy electrodes such as magnesium-silver alloy, magnesium-indium alloy, and aluminum-lithium alloy.
  • the film thickness of the cathode 6 is usually the same as that of the anode 2.
  • a cathode made of a low work function metal further laminating a metal layer having a high work function and stable to the atmosphere on the cathode increases the stability of the device.
  • metals such as aluminum, silver, copper, nickel, chromium, gold and platinum are used.
  • the element having the layer structure shown in FIG. 1 has been mainly described. However, the above description is provided as long as the performance is not impaired between the anode 2 and the cathode 6 and the light emitting layer 4 in the organic electroluminescent element of the present invention.
  • an arbitrary layer may be provided, and any layer other than the light emitting layer 4 may be omitted.
  • Examples of the layer that may be included include the electron transport layer 7.
  • the electron transport layer 7 is provided between the light emitting layer 4 and the electron injection layer 5 as shown in FIG. 2 for the purpose of further improving the luminous efficiency of the device.
  • the electron transport layer 7 is formed of a compound capable of efficiently transporting electrons injected from the cathode 6 between the electrodes to which an electric field is applied in the direction of the light emitting layer 4.
  • an electron transporting compound used for the electron transport layer 7 the electron injection efficiency from the cathode 6 or the electron injection layer 5 is high, and the injected electrons are transported efficiently with high electron mobility. It must be a compound that can
  • Examples of the material that satisfies such conditions include the charge transport material of the present invention.
  • metal complexes such as aluminum complexes of 8-hydroxyquinoline (JP 59-194 393), metal complexes of 10-hydroxybenzo [h] quinoline, oxadiazole derivatives, distyryl biphenyl derivatives, silole derivatives 3- or 5-hydroxyflavone metal complex, benzoxazole metal complex, benzothiazole metal complex, trisvens imidazolylbenzene (US Pat. No.
  • quinoxaline compound JP-A-6- 207169
  • phenant phosphorus derivatives JP-A-5-331459
  • 2-t-butyl-9,10-N ⁇ '-dicyananthraquinonedimine
  • n-type hydrogenated amorphous Examples include silicon carbide, n-type zinc sulfide, and n-type selenium zinc.
  • the thickness of the electron transport layer 7 is usually 1 nm, preferably about 5 nm, and the upper limit is usually about 300 nm, preferably about 10 nm.
  • the electron transport layer 7 is formed by laminating on the light emitting layer 4 by the wet film forming method or the vacuum deposition method in the same manner as the hole injection layer 3. Usually, a vacuum deposition method is used.
  • the hole blocking layer 8 has a function of confining holes and electrons in the light emitting layer 4 and improving luminous efficiency. That is, the hole blocking layer 8 is generated by increasing the probability of recombination with electrons in the light emitting layer 4 by blocking the holes moving from the light emitting layer 4 from reaching the electron transport layer 7. There are a role of confining excitons in the light emitting layer 4 and a role of efficiently transporting electrons injected from the electron transport layer 7 in the direction of the light emitting layer 4.
  • the hole blocking layer 8 serves to block the holes moving from the anode 2 from reaching the cathode 6, and efficiently transports the electrons injected from the cathode 6 toward the light emitting layer 4.
  • the compound that can be formed is laminated on the light emitting layer 4 so as to be in contact with the interface of the light emitting layer 4 on the cathode 6 side.
  • the physical properties required of the material constituting the hole blocking layer 8 include high electron mobility and low hole mobility, a large energy gap (difference between HOMO and LUMO), and excited triplet levels. (T1) is high.
  • the charge transport material of the present invention is preferably used.
  • the film thickness of the hole blocking layer 8 is usually 0.3 nm or more, preferably 0.5 nm or more, and usually ⁇ m or less, preferably 50 nm or less.
  • the hole blocking layer 8 can also be formed by the same method as the hole injection layer 3, but usually a vacuum evaporation method is used.
  • the electron transport layer 7 and the hole blocking layer 8 may be provided as necessary. 1) Only the electron transport layer, 2) Only the hole block layer, 3) The hole block layer Z electron transport There are usages such as layering, 4) not using, etc.
  • the hole blocking layer 8 it is also effective to provide an electron blocking layer 9 between the hole injection layer 3 and the light emitting layer 4 as shown in Figs.
  • the electron blocking layer 9 prevents electrons moving from the light emitting layer 4 from reaching the hole injection layer 3, thereby recombining with holes in the light emitting layer 4.
  • the characteristics required for the electron blocking layer 9 include a high energy gap (difference between HOMO and LUMO) with high hole transportability and a high excited triplet level (T1). Further, when the light emitting layer 4 is formed by a wet film forming method, it is preferable that the electron blocking layer 9 is also formed by a wet film forming method because the device can be easily manufactured.
  • the electron blocking layer 9 also has wet film formation compatibility.
  • the material used for such an electron blocking layer 9 include the charge transport material of the present invention, F8—TFB ⁇ .
  • examples thereof include a copolymer of dioctylfluorene and triphenylamine (described in WO2004Z084260).
  • the light-emitting layer is formed by a dry film formation method (evaporation method or the like)
  • a material used for the electron blocking layer 9 other than the charge transport material of the present invention
  • 4, 4 'bis [ N— (1 naphthyl) —N—phenylamino] aromatic diamines including two or more tertiary amins represented by biphenyl, wherein two or more condensed aromatic rings are substituted with nitrogen atoms special Kaihei 5-234681)
  • 4, 4 "—Tris (1-naphthylphenol-triamino) triphenylamine and other aromatic amine compounds having a starbust structure J.
  • R ′′ to R 19 each represent a hydrogen atom, an aryl group or an alkyl group. 1 to! ⁇ May be the same or different. R ′′ to R 19 represent an aryl. If groups or alkyl le group, R "to R 19 may further have a Ariru group or an alkyl group as a substituent.
  • polyarylene ether sulfone (Polym. Adv) containing polyvinylcarbazole, polyvinyltriphenylamine (Japanese Patent Laid-Open No. 7-53953), tetraphenylpentidine as a material for the electron blocking layer 9 is used. Tech., 7 ⁇ , 33, 199 6).
  • the structure opposite to that shown in Fig. 1, that is, the cathode 6, the electron injection layer 5, the light emitting layer 4, the hole injection layer 3, and the anode 2 can be laminated on the substrate 1 in this order.
  • the organic electroluminescent element of the present invention between two substrates, at least one of which has high transparency.
  • Sarako can also have a structure in which the layer configuration shown in FIG. 1 is stacked in multiple layers (a structure in which a plurality of light emitting units are stacked).
  • a structure in which a plurality of light emitting units are stacked instead of the interfacial layer (between the light emitting units) (two layers when the anode is IT 0 and the cathode is A1), for example, VO is used as the charge generation layer (CGL).
  • CGL charge generation layer
  • the present invention is effective when the organic electroluminescent device is a single device, a device having a structure arranged in an array, or a structure in which an anode and a cathode power are arranged in a matrix. However, it can be applied.
  • the glass transition temperature was determined by DSC measurement
  • the vaporization temperature was determined by TG-DTA measurement
  • the melting point was determined by DSC measurement or TG-DTA measurement.
  • the glass transition temperature of this product was 83 ° C.
  • the obtained solution was extracted with toluene, and the extracted solution was washed with an aqueous sodium hydrogen carbonate solution, anhydrous magnesium sulfate was added, and the solid content was removed by filtration and concentrated.
  • the target product I-2a and the target product I-3a were identified by 1 H-NMR (400 MHz; heavy acetone solvent) and DEI-MS.
  • Object I 2a was identified by 1 H-NMR (400 MHz; heavy acetone solvent) and DEI-MS.
  • the obtained solution was extracted with toluene, and the extracted solution was washed with an aqueous sodium hydrogen carbonate solution, anhydrous magnesium sulfate was added, and the solid content was removed by filtration and concentrated.
  • This was purified by silica gel column chromatography (developing solvent: n-hexane Z methylene chloride 5 Zl to 4 Zl) to obtain the target compound 1-2 (3.00 g).
  • the glass transition temperature of this product was 87 ° C, the crystallization temperature and melting point were not observed, and the vaporization start temperature was 531 ° C.
  • the resulting solution was extracted with dichloromethane, and the extracted solution was washed with brine, anhydrous magnesium sulfate and activated clay were added, and the solid content was removed by filtration and concentrated. This was purified by silica gel column chromatography to obtain the target product I-4a.
  • the glass transition temperature of this product was 99 ° C, the crystallization temperature and melting point were not observed, and the vaporization start temperature was 561 ° C.
  • the acid-reduction potential of the hydrocarbon compound (1-1) was measured by cyclic voltammetry.
  • ImolZL was dissolved in a solvent in which acetonitrile and tetrahydrofuran were mixed at a volume ratio of 1: 1 at 25 ° C, and a hydrocarbon compound (I Measurement was performed on a solution obtained by dissolving 1 mmol of ImmolZL.
  • the working electrode was glassy carbon (manufactured by BS Corporation), the counter electrode was a platinum wire, the reference electrode was a silver wire, and the running speed was measured as lOOmVZs.
  • the wavelength of the peak top observed at the shortest wavelength position was defined as the triplet excitation level (nm).
  • An organic electroluminescent device having the structure shown in FIG. 8 was produced by the following method.
  • An indium stannate oxide (ITO) transparent conductive film 150 nm deposited on glass substrate 1 (sputtered film product; sheet resistance 15 ⁇ ) is 2 mm using normal photolithography and hydrochloric acid etching.
  • Anode 2 was formed by patterning into stripes of width. The patterned ITO substrate was cleaned in the order of ultrasonic cleaning with acetone, water with pure water, and ultrasonic cleaning with isopropyl alcohol, then dried with nitrogen blow, and finally UV ozone cleaning.
  • the hole injection layer 3 was formed by a wet film forming method as follows.
  • Non-conjugated polymer compound (PB-1 (weight average molecular weight: 29400, number average molecular weight: 12600)) having an aromatic amino group having the following structural formula as a material for the hole injection layer 3 and the structure shown below
  • PB-1 weight average molecular weight: 29400, number average molecular weight: 12600
  • A-2 electron-accepting compound
  • a uniform thin film having a thickness of 30 nm was formed by the above spin coating.
  • the light emitting layer 4 was formed by a wet film forming method as follows.
  • the hydrocarbon compound (1-1) of the present invention synthesized in Synthesis Example 1 is charged with toluene as a solvent together with an iridium complex (D-1) having the structural formula shown below.
  • D-1 having the structural formula shown below.
  • Prepare material composition The charge transport material composition was spin coated under the following conditions.
  • composition I 1 Concentration in composition I 1 2.0% by weight
  • a uniform thin film having a thickness of 60 nm was formed by the above spin coating.
  • a pyridine derivative (HB-1) shown below was laminated as the hole blocking layer 8 at a crucible temperature of 260 to 264 ° C. and a film thickness of 5 nm at a deposition rate of 0.05 nmZ seconds.
  • the degree of vacuum during deposition was 3.9 X 10 _4 Pa (about 3. OX 10 _6 Torr).
  • an aluminum 8-hydroxyoxyquinoline complex (ET-1) shown below was deposited as the electron transport layer 7 in the same manner.
  • the crucible temperature of the aluminum 8-hydroxyquinoline complex is controlled in the range of 213 to 247 ° C, the vacuum during deposition is 3.9 X 10 _4 Pa (about 3. OX 10 _6 Torr), and the deposition rate was 0. InmZ seconds and the film thickness was 30 nm.
  • the substrate temperature during vacuum deposition of the hole blocking layer 8 and the electron transport layer 7 was kept at room temperature.
  • the element to which the electron transport layer 7 has been vapor-deposited is once taken out from the vacuum vapor deposition apparatus to the atmosphere, and a 2 mm wide striped shadow mask is used as a mask for cathode vapor deposition.
  • the anode 2 is in close contact with the ITO stripe perpendicular to the ITO stripe and placed in a separate vacuum deposition apparatus, and the degree of vacuum in the apparatus is 2.0 X 10 _6 Torr (about 2 6 X 10 _ 4 Pa).
  • lithium fluoride (LiF) was deposited using a molybdenum boat, the deposition rate was 0.07 nm / second, and the degree of vacuum was 2.2 X 10 _6 Torr (about 3.0 X 10 _4 Pa) was deposited on the electron transport layer 7 with a thickness of 0.5 nm.
  • the peak wavelength of the emission spectrum of the device was 470 nm, and it was identified as having iridium complex (D-1) power.
  • An organic electroluminescent device was produced in the same manner as in Example 1 except that an iridium complex (D-2) having the following structural formula was used instead of the iridium complex (D-1).
  • the maximum wavelength of the emission spectrum of the device was 512 nm, and it was identified as having an iridium complex (D-2) force.
  • the CIE chromaticity of luminescence was (0.295, 0.616).
  • the organic electroluminescent device using the hydrocarbon compound (1-1) of the present invention as the host material of the luminescent material is excellent in charge transporting property and is not easily crystallized. Thus, uniform light emission was obtained, and it was possible to drive at a low voltage with high light emission efficiency.
  • An organic electroluminescent device having the structure shown in FIG. 9 was produced by the following method.
  • the anode was formed by patterning into stripes of width.
  • the patterned ITO substrate was cleaned in the order of ultrasonic cleaning with acetone, water with pure water, and ultrasonic cleaning with isopropyl alcohol, then dried with nitrogen blow, and finally UV ozone cleaning.
  • the non-conjugated high molecular compound (PB-1) and the electron accepting compound (A-2) having an aromatic amino group used in Example 2 were used. Spin coating was performed under the same conditions as in 2 to form a uniform thin film with a thickness of 30 nm.
  • the substrate on which the hole injection layer 3 was formed was placed in a vacuum evaporation apparatus.
  • the device was evacuated using a cryopump until the degree of vacuum in the device was about 3.0 X 10 _4 Pa or less.
  • Deposition was carried out by heating the arylamine compound (EB-1) shown below, which was placed in a ceramic crucible arranged in the above apparatus, with a tantalum wire heater around the crucible.
  • the degree of vacuum at the time of deposition was 2.4 X 10 _4 Pa, the deposition rate was 0.1 nm Z seconds, and an electron blocking layer 9 having a thickness of 30 nm was obtained.
  • the compound (H—l) shown below as the main component (host material) of the light-emitting layer 4 and the organic iridium complex (D-1) as a subcomponent (dopant) were separately used.
  • the film was placed in a ceramic crucible and deposited by the binary simultaneous vapor deposition method.
  • the deposition rate of compound (H-1) was controlled at 0. InmZ seconds, the crucible temperature of iridium complex (D-1) was controlled at 251 to 254 ° C, the deposition rate was controlled at 0.008 nmZ seconds, and the film thickness was 30 nm.
  • the light emitting layer 4 containing 7% by weight of the lysium complex (D-1) was laminated on the electron blocking layer 9 .
  • the degree of vacuum during the deposition was 2.0 X 10 _4 Pa.
  • the hydrocarbon compound (1-1) of the present invention was laminated as a hole blocking layer 8 at a crucible temperature of 449 to 452 ° C with a deposition rate of 0. InmZ seconds and a film thickness of 5 nm.
  • the degree of vacuum at the time of deposition was 1.8 X 10 _4 Pa.
  • the aluminum 8-hydroxyquinoline complex (ET-1) was deposited as the electron transport layer 7 in the same manner.
  • the crucible temperature of the aluminum 8-hydroxyquinoline complex is controlled in the range of 239 to 244 ° C, the vacuum during deposition is 1.5 X 10 " 4 Pa, and the deposition rate is 0. InmZ seconds. Was 15 nm.
  • the substrate temperature during vacuum deposition of the electron blocking layer 9, the light emitting layer 4, the hole blocking layer 8 and the electron transporting layer 7 was kept at room temperature.
  • the element on which the electron transport layer 7 has been deposited is once taken out from the vacuum deposition apparatus into the atmosphere, and a 2 mm wide striped shadow mask is used as the cathode deposition mask.
  • the device was in close contact with the ITO stripe so as to be perpendicular to the ITO stripe, placed in a separate vacuum deposition apparatus, and evacuated until the degree of vacuum in the apparatus was 2. OX 10 _4 Pa or less in the same manner as the organic layer.
  • lithium fluoride (LiF) was deposited using a molybdenum boat, the deposition rate was 0.5 OlnmZ seconds, the degree of vacuum was 4.7 X 10 _5 Pa, and the thickness of the electron transport layer was 7 nm. A film was formed on the substrate.
  • aluminum was heated in the same molybdenum boat, deposition rate 0. 4NmZ sec, were laminated al Miniumu layer having a thickness of 80nm in vacuum 2. 5 X 10 _4 Pa.
  • the substrate temperature during deposition of the cathode buffer layer 10 and the cathode 6 was kept at room temperature.
  • An organic electroluminescent device having the structure shown in FIG. 9 was produced.
  • An organic electroluminescence device having a light emitting area portion of 2 mm ⁇ 2 mm in size was obtained in the same manner as in Example 4 except that the thickness of the electron transport layer 7 was changed to 30 nm.
  • An organic electroluminescent device having the structure shown in FIG. 9 was produced.
  • electron transport layer 7 (ET-2) as shown in Table 2 with a crucible temperature of 190 to 191 ° C and a deposition rate of 0. InmZ seconds and a thickness of 5 nm.
  • An organic electroluminescent element having an area portion was obtained.
  • An organic electroluminescent device having the structure shown in FIG. 9 was produced.
  • An organic electroluminescent device having a light emitting area portion of 2 mm ⁇ 2 mm in size was obtained in the same manner as in Example 5 except that the material used for the electron transport layer 7 was the above compound (ET-2).
  • An organic electroluminescent device having the structure shown in FIG. 9 was produced.
  • An organic electroluminescence device having an emission area portion of 2 mm ⁇ 2 mm in size was obtained in the same manner as in Example 7 except that the thickness of the hole blocking layer 8 was changed to 10 nm.
  • An organic electroluminescent device having the structure shown in FIG. 9 was produced.
  • the compound (ET-3) shown below as the electron transport layer 7 was formed in the same manner as in Example 7 except that the crucible temperature was 222 to 225 ° C, the deposition rate was 0. InmZ seconds, and the film thickness was 5 nm.
  • An organic electroluminescent element having a light emitting area portion of X 2 mm in size was obtained.
  • An organic electroluminescent device having the structure shown in FIG. 9 was produced.
  • An organic electroluminescent device having a light emitting area portion of 2 mm ⁇ 2 mm in size was obtained in the same manner as in Example 9 except that the thickness of the hole blocking layer 8 was changed to 10 nm.
  • An organic electroluminescent device having the structure shown in FIG. 9 was produced. In the same manner as in Examples 4 to 11, layers up to the electron blocking layer 9 were formed. Next, the compound (H-1) and the hydrocarbon compound (I 1) of the present invention are used as the main component (host material) of the light-emitting layer 4, and the organic iridium complex (D-1) is separately used as the subcomponent (dopant). The film was placed in a ceramic crucible and deposited by the ternary co-evaporation method.
  • the deposition rate of compound (H-1) is 0.05 nmZ seconds
  • the crucible temperature of compound (I-1) is 376-382 ° C
  • the deposition rate is 0.05 nmZ seconds
  • the temperature was controlled at 251 to 254 ° C
  • the deposition rate was controlled at 0.008 nmZ seconds
  • a light-emitting layer 4 containing 30% by weight of iridium complex (D-1) was laminated on the electron blocking layer 9 did.
  • the degree of vacuum during the deposition was 9.4 ⁇ 10 _5 Pa.
  • the compound (ET-2) was laminated as the hole blocking layer 8 at a crucible temperature of 225 to 226 ° C and a film thickness of 5 nm at a deposition rate of 0. InmZ seconds.
  • the degree of vacuum during deposition was 6.8 X 10 " 5 Pa.
  • a compound (ET-1) is deposited in the same manner as the electron transport layer 7. It was.
  • the substrate temperature during vacuum deposition of the electron blocking layer 9, the light emitting layer 4, the hole blocking layer 8 and the electron transport layer 7 was kept at room temperature.
  • An organic electroluminescent device having the structure shown in FIG. 9 was produced.
  • An organic electroluminescent element having a light emitting area of 2 mm ⁇ 2 mm in size was obtained in the same manner as in Example 11 except that the thickness of the electron transport layer 7 was changed to 30 nm.
  • An organic electroluminescent device having the structure shown in FIG. 9 was produced.
  • An organic electroluminescent device having a light emitting area portion of 2 mm ⁇ 2 mm in size was obtained in the same manner as in Example 11 except that the hole blocking layer 8 was not laminated on the light emitting layer 4.
  • An organic electroluminescent device having the structure shown in FIG. 9 was produced.
  • An organic electroluminescent element having a light emitting area portion of 2 mm ⁇ 2 mm in size was obtained in the same manner as in Example 12 except that the hole blocking layer 8 was not laminated on the light emitting layer 4.
  • An organic electroluminescent device having the structure shown in FIG. 9 was produced. In the same manner as in Examples 4 to 14, each layer up to the electron blocking layer 9 was formed.
  • the light emitting layer 4 was further vapor-deposited as a laminated structure of two layers.
  • the compound (H-1) as the main component (host material) and the organic iridium complex (D) was further vapor-deposited as a laminated structure of two layers.
  • the compound (H-1) as the main component (host material) and the organic iridium complex (D) was further vapor-deposited as a laminated structure of two layers.
  • the compound (1-1) of the present invention is used as the main component (host material), and the organic iridium complex (D-1) is used as the subcomponent (dopant).
  • the film was placed in a ceramic crucible and deposited by the binary simultaneous vapor deposition method.
  • the crucible temperature of compound (I-1) is 396-397 ° C, the deposition rate is 0. InmZ seconds, the crucible temperature of iridium complex (D-1) is 256-257 ° C, the deposition rate is 0.008 nmZ seconds.
  • the second layer of the light emitting layer 4 having a thickness of lOnm and containing 7% by weight of iridium complex (D-1) was laminated on the first layer of the light emitting layer 4.
  • the degree of vacuum during deposition was 2.1 X 10 _4 Pa.
  • a compound (ET-2) was laminated as a hole blocking layer 8 at a crucible temperature of 225 to 226 ° C. and a film thickness of 5 nm at a deposition rate of 0. InmZ seconds.
  • the degree of vacuum during deposition was 1.6 X 10 " 4 Pa.
  • the crucible temperature of the compound (ET-1) at this time is controlled in the range of 233 to 236 ° C, the degree of vacuum during deposition is 1.6 X 10 _4 Pa, the deposition rate is 0. InmZ seconds, and the film thickness is 30 nm. It was.
  • the substrate temperature during vacuum deposition of the electron blocking layer 9, the light emitting layer 4, the hole blocking layer 8, and the electron transport layer 7 was kept at room temperature.
  • An organic electroluminescent device having the structure shown in FIG. 9 was produced.
  • An organic electroluminescent device having the structure shown in FIG. 9 was produced.
  • An organic electroluminescent device having a light emitting area portion of 2 mm ⁇ 2 mm in size was obtained in the same manner as in Example 15 except that the hole blocking layer 8 was not laminated on the light emitting layer 4.
  • An organic electroluminescent device having the structure shown in FIG. 9 was produced. Emission of 2 mm x 2 mm in size as in Example 16 except that the hole blocking layer 8 is not laminated on the light emitting layer 4 An organic electroluminescent element having an area portion was obtained.
  • An organic electroluminescent device having the structure shown in FIG. 9 was produced.
  • the light emitting layer 4 was formed as follows. Install the compound (1-1) of the present invention as the main component (host material) of the light-emitting layer 4 and the organic iridium complex (D-2) used in Example 3 as a subcomponent (dopant) in separate ceramic crucibles. Then, the film was formed by the binary simultaneous vapor deposition method.
  • the deposition rate of compound (1-1) was controlled at 0.08 nmZ seconds, and the deposition rate of iridium complex (D-2) was controlled at 0.005 nm / second, respectively. Is formed into a light emitting layer 4 containing 6% by weight. At this time, the temperature of the crucible of the compound (1-1) is 396 ⁇ 4 36 ° C, the temperature of the crucible of the iridium complex (D-2) is 271 ⁇ 273 ° C, and the vacuum is 1.2 X 10 _ 4 Pa there were.
  • the pyridine derivative (HB-1) was deposited as a hole blocking layer 8 to a thickness of 5 nm at a deposition rate of 0.09 nm /.
  • the temperature of the crucible of the pyridine derivative (HB-1) was 26 2 to 264 ° C., and the degree of vacuum was 1. OX 10 _4 Pa.
  • the substrate temperature during vacuum deposition of the light emitting layer 4 and the hole blocking layer 8 was maintained at room temperature.
  • An organic electroluminescent device having the structure shown in FIG. 9 was produced.
  • the light emitting layer 4 was formed as follows.
  • the film was deposited by the binary co-evaporation method.
  • the deposition rate of compound (1-3) was controlled at 0. InmZ seconds and the deposition rate of iridium complex (D-2) was controlled at 0.006 nmZ seconds, respectively, and the iridium complex (D-2) at a film thickness of 32 nm. A light emitting layer 4 containing 6 wt% was formed. Temperature of the crucible at this time iridium complex (D-2) is 27 2 ⁇ 275 ° C, vacuum degree: 1. was 1 X 10 _4 Pa.
  • a 5 nm film of pyridine derivative (HB-1) was deposited as the hole blocking layer 8 at a deposition rate of 0.09 nmZ seconds.
  • the temperature of the crucible (HB-1) was 262 to 264 ° C, and the degree of vacuum was 1. OX 10 _4 Pa.
  • the substrate temperature during vacuum deposition of the light emitting layer 4 and the hole blocking layer 8 was kept at room temperature.
  • An organic electroluminescent device having the structure shown in FIG. 9 was produced.
  • the substrate on which the hole injection layer 3 was formed was placed in a vacuum evaporation apparatus.
  • the degree of vacuum in the equipment is about 3.OX Exhaust using a cryopump until 10 _4 Pa or less.
  • 4 X 10 _5 Pa the deposition rate was obtained an electron blocking layer 9 having a thickness 40nm with 0. InmZ seconds.
  • the temperature of the crucible was 247 to 263 ° C, and the degree of vacuum was 2.4 X 10 _5 Pa.
  • the light emitting layer 4 was formed.
  • the hydrocarbon compound (1-1) of the present invention as the main component (host material) of the light-emitting layer 4 and the organic iridium complex (D-2) as the subcomponent (dopant) are placed in separate ceramic crucibles, Film formation was performed by the two-component simultaneous vapor deposition method.
  • the deposition rate of compound (1-1) was controlled at 0.08 nmZ seconds, and the deposition rate of iridium complex (D-2) was controlled at 0.005 nm / second, respectively. Is formed into a light emitting layer 4 containing 6% by weight.
  • the temperature of the crucible of the compound (1-1) is 333 to 3 34 ° C
  • the temperature of the crucible of the iridium complex (D-2) is 269 to 271 ° C
  • the degree of vacuum is 3.5 X 10 _ 5 Pa. there were.
  • a pyridine derivative (HB-1) was formed as a hole blocking layer 8 to a thickness of 5 nm at a deposition rate of 0.09 nmZ seconds.
  • the temperature of the crucible of the pyridine derivative (HB-1) was 239 to 242 ° C., and the degree of vacuum was 3.1 ⁇ 10 _5 Pa.
  • the substrate temperature during vacuum deposition of the light emitting layer 4 and the hole blocking layer 8 was kept at room temperature.
  • An organic electroluminescent device having the structure shown in FIG. 9 was produced.
  • the light emitting layer 4 was formed as follows.
  • the following power rubazole derivative (EM-1) as the main component (host material) of the light-emitting layer 4 and organic iridium complex (D-2) as the secondary component (dopant) are placed in separate ceramic crucibles, and two-way simultaneous Film formation was performed by the evaporation method.
  • the deposition rate of the compound (EM-1) was controlled at 0.07 nmZ seconds and the deposition rate of the iridium complex (D-2) was controlled at 0.004 nmZ seconds. ) was formed into a light-emitting layer 4 containing 6.4% by weight. At this time, the temperature of the crucible of the iridium complex (D-2) was 243 ° C, and the degree of vacuum was 7.1 X 10 _5 Pa.
  • the hydrocarbon compound (1-1) of the present invention was deposited as a hole blocking layer 8 at a deposition rate of 0.08 nm Z seconds for 5 nm.
  • the substrate temperature during vacuum deposition of the light emitting layer 4 and the hole blocking layer 8 was kept at room temperature.
  • Example 23 Production of organic electroluminescent device
  • An organic electroluminescent device having the structure shown in FIG. 9 was produced.
  • the light emitting layer 4 was formed as follows. Power rubazole derivative (EM-1) as the main component (host material) of light-emitting layer 4 and organic iridium complex (D-2) as the secondary component (dopant) are installed in separate ceramic crucibles, and two-component simultaneous vapor deposition method The film was formed by.
  • EM-1 Power rubazole derivative
  • D-2 organic iridium complex
  • the deposition rate of the compound (EM—1) was controlled at 0.07 nmZ seconds, and the deposition rate of the iridium complex (D—2) was controlled at 0.004 nmZ seconds. ) was formed into a light-emitting layer 4 containing 6.4% by weight. At this time, the temperature of the crucible of the iridium complex (D-2) was 243 ° C, and the degree of vacuum was 7.1 X 10 _5 Pa.
  • the hydrocarbon compound (1-2) of the present invention synthesized in Synthesis Example 2 was deposited as a hole blocking layer 8 at a deposition rate of 0.08 nmZ seconds to a thickness of 5 nm.
  • the temperature of the crucible of the compound (1-2) was 398 to 405 ° C., and the degree of vacuum was 6.5 ⁇ 10 _5 Pa.
  • the substrate temperature during vacuum deposition of the light emitting layer 4 and the hole blocking layer 8 was kept at room temperature.
  • a device was fabricated in the same manner as in Example 21 except that the following power rubazole derivative (EM-1) was used as the main component of the light-emitting layer 4.
  • the light emitting layer 4 is formed by placing a compound (EM-1) as a main component (host material) and an organic iridium complex (D-2) as a subcomponent (dopant) in separate ceramic crucibles, Film formation was performed by the two-component simultaneous vapor deposition method.
  • the deposition rate of the compound (EM—1) was controlled at 0.08 nmZ seconds, and the deposition rate of the iridium complex (D—2) was controlled at 0.005 nm / sec. A light emitting layer 4 containing 6% by weight of 2) was formed. At this time, the temperature of the crucible of the iridium complex (D-2) was 261 to 265 ° C, and the degree of vacuum was 1.2 X 10 _4 Pa.
  • a pyridine derivative (HB-1) was deposited as a hole blocking layer 8 at a deposition rate of 0.09 nmZ seconds.
  • the temperature of the pyridine derivative (HB-1) crucible at this time is 239-242 ° C
  • the degree of vacuum was 3.1 X 10 _5 Pa.
  • a device was produced in the same manner as in Example 19 except that the compound (C-1) was used as the main component of the light emitting layer 4. At this time, the light-emitting layer 4 is formed by using a compound (C)
  • the deposition rate of compound (C-1) was controlled at 0.08 nmZ seconds and the deposition rate of iridium complex (D-2) was controlled at 0.005 nm / second, respectively. Is formed into a light emitting layer 4 containing 6% by weight.
  • the compound temperature of crucible (C 1) is 331 to 337 ° C
  • the temperature of the crucible of iridium complex (D-2) is 240 ⁇ 241 ° C
  • vacuum degree was 7. 5 X 1 0 _5 Pa .
  • a pyridine derivative (HB-1) was deposited as a hole blocking layer 8 at a thickness of 5 nm at a deposition rate of 0.09 nmZ seconds.
  • the temperature of the crucible of the pyridine derivative (HB-1) was 231 to 236 ° C., and the degree of vacuum was 6.6 ⁇ 10 _5 Pa.
  • the light emission characteristics of the devices obtained in Examples 4 to 18 are summarized in Table 5.
  • Table 5 the maximum luminance is the value at current density of 0.25 AZcm 2 , luminous efficiency, luminance Z current, voltage is the value at luminance lOOcdZm 2 , voltage @ 2500 cd, luminance Z current @ 2500 cd is luminance at 2500 cdZm 2 Each value is shown.
  • the maximum wavelength of the emission spectrum of the device was 471 nm, and it was identified to be from the organic iridium complex (D-1).
  • Example 19 23 and Comparative Example 23 The light emission characteristics of the devices obtained in Example 19 23 and Comparative Example 23 are summarized in Table 6. .
  • Table 6 the maximum emission luminance value at a current density of 0. 25AZcm 2, luminous efficiency, luminance Z current, voltage value of the luminance LOOcdZm 2, voltage @ 2500 cd, luminance Z current @ 2500 cd are at luminance 2500CdZm 2 Are shown respectively.
  • the maximum wavelength of the emission spectrum of the device was 512 ⁇ m, and it was identified as having an organic iridium complex (D-2) force.
  • Example 20 The devices fabricated in Example 20, Example 21, and Comparative Example 2 were subjected to a continuous current test under the following conditions.
  • Example 19 The devices fabricated in Example 19 and Comparative Example 3 were subjected to a continuous current test under the following conditions.

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JP7379601B2 (ja) 2007-08-08 2023-11-14 ユニバーサル ディスプレイ コーポレイション リン光発光ダイオード中の単一トリフェニレン発色団
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DE102008033943A1 (de) 2008-07-18 2010-01-21 Merck Patent Gmbh Neue Materialien für organische Elektrolumineszenzvorrichtungen
TWI775802B (zh) * 2017-01-23 2022-09-01 日商三菱化學股份有限公司 發光層形成用組成物以及含有該發光層形成用組成物的有機電場發光元件
WO2018135656A1 (ja) * 2017-01-23 2018-07-26 三菱ケミカル株式会社 発光層形成用組成物及び該発光層形成用組成物を含有する有機電界発光素子
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