WO2022234763A1 - 有機電界発光素子用組成物、有機電界発光素子、表示装置及び照明装置 - Google Patents
有機電界発光素子用組成物、有機電界発光素子、表示装置及び照明装置 Download PDFInfo
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- WO2022234763A1 WO2022234763A1 PCT/JP2022/017478 JP2022017478W WO2022234763A1 WO 2022234763 A1 WO2022234763 A1 WO 2022234763A1 JP 2022017478 W JP2022017478 W JP 2022017478W WO 2022234763 A1 WO2022234763 A1 WO 2022234763A1
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Images
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- C—CHEMISTRY; METALLURGY
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- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
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- C09D11/30—Inkjet printing inks
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- C—CHEMISTRY; METALLURGY
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
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- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H10K50/00—Organic light-emitting devices
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- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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Definitions
- the present invention relates to a composition for organic electroluminescent elements useful for forming a light-emitting layer of an organic electroluminescent element (hereinafter sometimes referred to as "organic EL element").
- organic EL element an organic electroluminescent device having a light-emitting layer formed using the composition for organic electroluminescent devices, a method for producing the same, and a display device and a lighting device having the organic electroluminescent device.
- organic electroluminescence element consumes little power because of low applied voltage, and is capable of emitting three primary colors. For this reason, it is starting to be applied not only to large display monitors, but also to small and medium-sized displays such as mobile phones and smart phones.
- An organic electroluminescent device is manufactured by stacking multiple layers such as a light-emitting layer, charge injection layer, and charge transport layer.
- a light-emitting layer such as a light-emitting layer, charge injection layer, and charge transport layer.
- most organic electroluminescent devices are manufactured by vapor-depositing organic materials under vacuum.
- the vacuum vapor deposition method has a complicated vapor deposition process and is inferior in productivity.
- the wet film-forming method (coating method) has been studied as a process for efficiently manufacturing organic electroluminescent elements that can be used for large displays and lighting.
- the wet film-forming method has the advantage that a stable layer can be easily formed as compared with the vacuum deposition method. Therefore, it is expected to be applied to mass production of displays and lighting devices and to large-sized devices.
- an organic electroluminescence device In order to manufacture an organic electroluminescence device by a wet film-forming method, it is necessary to dissolve a functional material in an organic solvent and use it as an ink. If the solubility of the functional material in the organic solvent is low, the material may deteriorate before use because it requires an operation such as heating for a long period of time. In addition, if the uniform state cannot be maintained for a long time in a solution state, the material will precipitate from the solution, making it impossible to form a film using an inkjet device or the like.
- the organic solvent used for the ink is required to have solubility in two senses: to quickly dissolve the functional material, and to maintain a uniform state without precipitating the functional material after dissolution.
- Patent Documents 1 and 2 In recent years, attempts have been made to incorporate a phenol derivative into the ink for the purpose of suppressing deterioration in the luminous efficiency and drive life of the organic electroluminescent device even when the organic electroluminescent device is manufactured after the ink has been stored for a long time.
- Patent Documents 1 and 2 For example, Patent Documents 1 and 2.
- the present invention provides a composition for an organic electroluminescent element, which is used for forming a light-emitting layer in an organic electroluminescent element by wet film formation, and which has improved stability of liquid properties, especially surface tension stability of ink. is the subject.
- the present inventor found that by using an aliphatic ester and/or aromatic diester solvent having two or more carbonyl groups as a solvent, changes in liquid physical properties are reduced even when a phenol derivative is contained.
- the gist of the present invention is as follows.
- a composition for an organic electroluminescence device comprising a functional material, a compound represented by the following formula (1), and an aliphatic ester solvent and/or an aromatic diester solvent having two or more carbonyl groups.
- a is an integer of 0 to 4
- R 1 and R 2 each independently represent an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms.
- a is an integer of 2 to 4
- multiple R 2 may be the same or different.
- composition for an organic electroluminescence device wherein the aliphatic ester solvent having two or more carbonyl groups is a compound having two ester groups.
- composition for an organic electroluminescence device wherein the aliphatic ester solvent having two or more carbonyl groups is a compound having one ester group and one ketone group.
- R 24 represents an alkylene group.
- R 25 and R 26 each independently represent an alkyl group.
- R 24 and R 25 may combine with each other to form a ring.
- R 27 represents an alkylene group.
- R 28 and R 29 each independently represent an alkyl group.
- R 27 and R 28 or R 27 and R 29 may combine with each other to form a ring.
- Ar 31 represents an arylene group.
- R 30a and R 30b each independently represent an alkyl group.
- R 30a and Ar 31 may combine with each other to form a ring.
- composition for an organic electroluminescence device according to any one of [1] to [5], wherein the compound represented by formula (1) is a compound represented by formula (1-1) below.
- R 3 , R 4 and R 5 each independently represent an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms.
- b is an integer of 2 to 3
- multiple R 5 may be the same or different.
- composition for an organic electroluminescence device according to any one of [1] to [7], which contains an iridium complex as the functional material.
- composition for an organic electroluminescence device according to [8] which contains an iridium complex represented by the following formula (2) as the functional material.
- R 7 and R 8 each independently represent an alkyl group having 1 to 20 carbon atoms, a (hetero)aralkyl group having 7 to 40 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, (hetero)aryloxy groups of ⁇ 20, alkylsilyl groups of 1 to 20 carbon atoms, arylsilyl groups of 6 to 20 carbon atoms, alkylcarbonyl groups of 2 to 20 carbon atoms, arylcarbonyl groups of 7 to 20 carbon atoms, Any one of an alkylamino group having 1 to 20 carbon atoms, an arylamino group having 6 to 20 carbon atoms, and a (hetero)aryl group having 3 to 30 carbon atoms, or a combination thereof.
- R 7 and R 8 may further have a substituent.
- the plurality of R 7 and R 8 may be the same or different.
- Adjacent R 7 or R 8 bonded to a benzene ring may be bonded to each other to form a ring condensed to the benzene ring.
- d is an integer from 0 to 4;
- e is an integer from 0 to 3;
- m is an integer from 1 to 20;
- n is an integer of 0-2.
- Ring A is any one of pyridine ring, pyrazine ring, pyrimidine ring, imidazole ring, oxazole ring, thiazole ring, quinoline ring, isoquinoline ring, quinazoline ring, quinoxaline ring, azatriphenylene ring and carboline ring.
- Ring A may have a substituent, and the substituent is a fluorine atom, a chlorine atom, a bromine atom, an alkyl group having 1 to 20 carbon atoms, a (hetero)aralkyl group having 7 to 40 carbon atoms, a carbon alkoxy groups of 1 to 20 carbon atoms, (hetero)aryloxy groups of 3 to 20 carbon atoms, alkylsilyl groups of 1 to 20 carbon atoms, arylsilyl groups of 6 to 20 carbon atoms, alkylcarbonyl groups of 2 to 20 carbon atoms , an arylcarbonyl group having 7 to 20 carbon atoms, an alkylamino group having 2 to 20 carbon atoms, an arylamino group having 6 to 20 carbon atoms, and a (hetero)aryl group having 3 to 20 carbon atoms, or A combination of these.
- the substituent is a fluorine atom, a chlorine atom, a bromine atom
- Adjacent substituents bonded to ring A may be bonded to form a ring condensed to ring A.
- Z 1 represents a direct bond or an m+1 valent aromatic linking group.
- L 1 represents an ancillary ligand.
- l is an integer of 1-3. When there are multiple ancillary ligands, they may be different or the same. ]
- a method for producing an organic electroluminescent device comprising the step of forming a light-emitting layer by a wet film-forming method using the composition for an organic electroluminescent device according to any one of [1] to [10].
- a display device comprising the organic electroluminescence device according to [12].
- the composition for organic electroluminescent elements of the present invention is excellent in stability of liquid physical properties, especially in stability of ink surface tension. Therefore, even if the composition for an organic electroluminescent element of the present invention is stored for a long period of time and then used for the production of an organic electroluminescent element, there is little decrease in luminous efficiency and drive life, and further, there is little change in liquid physical properties, resulting in unevenness. A small display device or illumination device can be obtained. That is, the composition for organic electroluminescence elements of the present invention is a composition that can be applied to large-area coating and can be stored for a long period of time.
- the action mechanism by which such effects are obtained is presumed as follows. Since the composition for organic electroluminescence elements of the present invention contains the compound represented by the formula (1), which is a phenol derivative, deterioration of the functional material is suppressed even when the ink is stored for a long period of time. Furthermore, since an aliphatic ester and/or aromatic diester solvent having two or more carbonyl groups is contained as a solvent, it is possible to reduce changes in liquid physical properties due to oxidation of the phenol derivative.
- phenol derivative By including a phenol derivative in the ink, deterioration due to oxidation of the functional material is suppressed, but the phenol derivative itself is thought to be oxidized.
- phenols When phenols are oxidized, they usually become phenoxy radicals by proton transfer or hydrogen atom transfer after one-electron oxidation. After that, it is not clear whether the phenoxy radicals are further changed into other substances such as benzoquinones or peroxides in the ink, but in any case, the structure is such that no phenolic hydroxy group exists.
- a phenolic hydroxy group exhibits hydrogen-bonding properties and also exhibits acidity due to the resonance effect of an aromatic ring, and these properties are considered to change greatly when oxidized.
- FIG. 1 is a cross-sectional view schematically showing an example of the structure of the organic electroluminescence device of the present invention.
- a (hetero)aralkyl group, a (hetero)aryloxy group, and a (hetero)aryl group refer to an aralkyl group which may contain a heteroatom, an aryloxy group which may contain a heteroatom, and a heteroatom, respectively. represents an aryl group which may contain atoms.
- the term "may contain a heteroatom” means that one or more carbon atoms forming the main skeleton of an aryl group, an aralkyl group or an aryloxy group are substituted with a heteroatom.
- Heteroatoms include a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, a silicon atom and the like. Among them, a nitrogen atom is preferable from the viewpoint of durability. The same applies to (hetero)arylene groups.
- aromatic linking group means not only an aromatic hydrocarbon linking group, i.e., a linking group having an aromatic hydrocarbon ring, but also a heteroaromatic linking group, i.e., having a heteroaromatic ring Represents a broadly defined aromatic linking group that includes linking groups.
- composition for organic electroluminescence device comprises a functional material, a compound represented by the following formula (1), and an aliphatic ester solvent and/or an aromatic diester solvent having two or more carbonyl groups. It is characterized by
- a is an integer of 0 to 4.
- R 1 and R 2 each independently represent an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms.
- a is an integer of 2 to 4, multiple R 2 may be the same or different.
- the composition for organic electroluminescence elements of the present invention contains a functional material.
- a functional material is a light-emitting material or a charge-transporting material contained in the light-emitting layer of an organic electroluminescent device.
- composition for an organic electroluminescent element of the present invention preferably contains a phosphorescent organometallic complex as a functional material in that the excited triplet state energy can contribute to light emission. It preferably contains an iridium complex, which is an organometallic complex serving as a central element.
- the iridium complex contained in the composition for organic electroluminescence elements of the present invention is preferably represented by the following formula (2) in terms of high solubility in organic solvents and high heat resistance.
- R 7 and R 8 each independently represent an alkyl group having 1 to 20 carbon atoms, a (hetero)aralkyl group having 7 to 40 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, (hetero)aryloxy groups of ⁇ 20, alkylsilyl groups of 1 to 20 carbon atoms, arylsilyl groups of 6 to 20 carbon atoms, alkylcarbonyl groups of 2 to 20 carbon atoms, arylcarbonyl groups of 7 to 20 carbon atoms, Any one of an alkylamino group having 1 to 20 carbon atoms, an arylamino group having 6 to 20 carbon atoms, and a (hetero)aryl group having 3 to 30 carbon atoms, or a combination thereof.
- R 7 and R 8 may further have a substituent.
- the plurality of R 7 and R 8 may be the same or different.
- Adjacent R 7 or R 8 bonded to a benzene ring may be bonded to each other to form a ring condensed to the benzene ring.
- d is an integer from 0 to 4;
- e is an integer from 0 to 3;
- m is an integer from 1 to 20;
- n is an integer of 0-2.
- Ring A is any one of pyridine ring, pyrazine ring, pyrimidine ring, imidazole ring, oxazole ring, thiazole ring, quinoline ring, isoquinoline ring, quinazoline ring, quinoxaline ring, azatriphenylene ring and carboline ring.
- Ring A may have a substituent, and the substituent is a fluorine atom, a chlorine atom, a bromine atom, an alkyl group having 1 to 20 carbon atoms, a (hetero)aralkyl group having 7 to 40 carbon atoms, a carbon alkoxy groups of 1 to 20 carbon atoms, (hetero)aryloxy groups of 3 to 20 carbon atoms, alkylsilyl groups of 1 to 20 carbon atoms, arylsilyl groups of 6 to 20 carbon atoms, alkylcarbonyl groups of 2 to 20 carbon atoms , an arylcarbonyl group having 7 to 20 carbon atoms, an alkylamino group having 2 to 20 carbon atoms, an arylamino group having 6 to 20 carbon atoms, and a (hetero)aryl group having 3 to 20 carbon atoms, or A combination of these.
- the substituent is a fluorine atom, a chlorine atom, a bromine atom
- Adjacent substituents bonded to ring A may be bonded to form a ring condensed to ring A.
- Z 1 represents a direct bond or an m+1 valent aromatic linking group.
- L 1 represents an ancillary ligand.
- l is an integer of 1-3. When there are multiple ancillary ligands, they may be different or the same. ]
- R 7 and R 8 are each independently an alkyl group having 1 to 20 carbon atoms, a (hetero)aralkyl group having 7 to 40 carbon atoms, or 6 to 20 carbon atoms, from the viewpoint of durability. or a (hetero)aryl group having 3 to 30 carbon atoms, an alkyl group having 1 to 20 carbon atoms, a (hetero)aralkyl group having 7 to 40 carbon atoms, or 3 to 20 carbon atoms is more preferably a (hetero)aryl group of
- Two adjacent R7 groups and R8 groups may be linked to each other to form a ring condensed to the benzene ring to which these groups are linked.
- d is preferably 0 for ease of manufacture. d is preferably 1 or 2, more preferably 1, in terms of enhancing the solubility. Preferably, d is 2 when two adjacent R7s are linked together to form a ring.
- e is preferably 0 for ease of manufacture. e is preferably 1 or 2, more preferably 1, in terms of enhancing durability and solubility. e is preferably 2 or 3 when two adjacent R 8s are linked to each other to form a ring.
- R 7 and R 8 further have a substituent
- the substituent may be a fluorine atom, a chlorine atom, a bromine atom, an alkyl group having 1 to 20 carbon atoms, a (hetero)aralkyl group having 7 to 40 carbon atoms, or a (hetero)aralkyl group having 7 to 40 carbon atoms.
- m is preferably 2 or more.
- a phenyl group having a terminal t-butyl group has little contribution to charge transport and light emission. Therefore, m is preferably 8 or less, more preferably 4 or less.
- the iridium complex represented by the formula (2) has 4 or more, particularly 6 or more, and 48 or less, particularly 24 or less terminal t-butyl groups as a whole in the iridium complex, so that solubility and a low driving voltage are obtained. , is preferable in terms of compatibility with high luminous efficiency.
- n is preferably 0 or 1 for ease of production. It is preferable that n is 0 because there is little concern that the drive voltage will increase. n is preferably 1 or 2 in that the solubility is enhanced.
- ring A is preferably a pyridine ring, a pyrimidine ring, or an imidazole ring, and more preferably a pyridine ring.
- the hydrogen atom on ring A is an alkyl group having 1 to 20 carbon atoms, a (hetero) aralkyl group having 7 to 40 carbon atoms, a (hetero) ) substituted with an aryl group. Hydrogen atoms on ring A are preferably unsubstituted for ease of production.
- the hydrogen atom on ring A is substituted with a phenyl group or naphthyl group, which may have a substituent, so that excitons are easily generated when used in an organic electroluminescent device, so the luminous efficiency is preferable in that the
- Ring A forms a quinoline ring, isoquinoline ring, quinazoline ring, quinoxaline ring, azatriphenylene ring, or carboline ring by forming a condensed ring in which the substituents on ring A are bonded to each other and condensed on ring A.
- ring A is preferably a quinoline ring, an isoquinoline ring, or a quinazoline ring in terms of durability and red light emission.
- Z 1 is preferably a direct bond for ease of manufacture.
- Z 1 is preferably an (m+1)-valent aromatic linking group because there is little concern that the driving voltage will increase.
- Z 1 is preferably a phenylene group, a biphenylene group, a terphenylene group or a fluorenediyl group, particularly preferably a p-phenylene group, from the viewpoint of durability.
- Z 1 contains a benzene ring with bonding positions at 1,3,5-positions or a triazine ring with bonding positions at 2,4,6-positions from the viewpoint of durability. is preferred.
- Z 1 preferably contains a trivalent group represented by the following formula (2-2A) or (2-2B).
- the group represented by formula (2-2A) or (2-2B) is more preferably bonded to the benzene ring or ring A that bonds to iridium.
- L 1 is an ancillary ligand.
- L 1 is preferably a monovalent bidentate ligand, more preferably selected from ligands represented by the following formulas (2A), (2B) and (2C) .
- Broken lines in the following formulas (2A) to (2C) represent coordinate bonds.
- the ancillary ligands L 1 may have the same or different structures.
- L1 does not exist.
- R 9 and R 10 are selected from the same group as R 7 and R 8 above, and preferred examples are also the same.
- g is an integer from 0 to 4.
- h is an integer from 0 to 4; It is preferable that g and h are 0 in terms of easy production.
- g and h are preferably 1 or 2, more preferably 1, from the viewpoint of enhancing the solubility.
- Ring B is any one of pyridine ring, pyrimidine ring, imidazole ring, quinoline ring, isoquinoline ring, quinazoline ring, quinoxaline ring, azatriphenylene ring, carboline ring, benzothiazole ring and benzoxazole ring. These may have a substituent.
- Ring B is preferably a pyridine ring, a pyrimidine ring, or an imidazole ring, more preferably a pyridine ring, from the viewpoint of durability.
- the hydrogen atom on ring B is an alkyl group having 1 to 20 carbon atoms, a (hetero) aralkyl group having 7 to 40 carbon atoms, a (hetero) ) substituted with an aryl group.
- a hydrogen atom on ring B is preferably unsubstituted for ease of production.
- the hydrogen atom on ring B is substituted with a phenyl group or naphthyl group that may have a substituent, which facilitates the generation of excitons when used in an organic electroluminescent device, so the luminous efficiency is preferable in that the
- Ring B forms a quinoline ring, isoquinoline ring, quinazoline ring, quinoxaline ring, azatriphenylene ring, or carboline ring by forming a condensed ring in which the substituents on ring B are bonded to each other to form a condensed ring on ring B.
- ring B is preferably a quinoline ring, an isoquinoline ring, or a quinazoline ring in terms of durability and red light emission.
- each of R 11 to R 13 is independently substituted with a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may be substituted with a fluorine atom, or an alkyl group having 1 to 20 carbon atoms. also represents a phenyl group or a halogen atom. More preferably, R 11 and R 13 are a methyl group or a t-butyl group, and R 12 is a hydrogen atom, a C 1-20 alkyl group or a phenyl group.
- the compound represented by the formula (2) is also preferably a compound represented by the following formula (2-2) in which adjacent R 8 bonds together to form a fluorene ring.
- R 7 , d, m, n, ring A, Z 1 , L 1 , l are represented by R 7 , d, m, n, ring A, Z 1 , L 1 is synonymous with l.
- R 15 to R 17 are substituents.
- R 15 examples include the aforementioned substituents that R 8 may have. More preferably, R 15 is an alkyl group having 1 to 20 carbon atoms, or an aromatic hydrocarbon group having 6 to 30 carbon atoms which may be substituted with one or two alkyl groups having 1 to 20 carbon atoms.
- the aromatic hydrocarbon group having 6 to 30 carbon atoms means a monocyclic ring, a bicyclic condensed ring, a tricyclic condensed ring, or a group in which a plurality of monocyclic, bicyclic condensed rings, or tricyclic condensed rings are linked.
- R 15 is more preferably an alkyl group having 1 to 20 carbon atoms, particularly preferably an alkyl group having 1 to 8 carbon atoms.
- R 16 and R 17 are a part of R 8 or a substituent that R 8 may have, preferably each independently, an alkyl group having 1 to 12 carbon atoms, or 1 or 2 carbon atoms an aromatic hydrocarbon group having 6 to 20 carbon atoms which may be substituted with an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, or one or two alkoxy groups having 1 to 12 carbon atoms; It is an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms.
- the aromatic hydrocarbon group having 6 to 20 carbon atoms is a monocyclic, bicyclic condensed ring, or tricyclic condensed ring, or a group in which a plurality of monocyclic, bicyclic condensed, or tricyclic condensed rings are linked.
- R 16 and R 17 are more preferably each independently an alkyl group having 1 to 8 carbon atoms, or 6 or 12 carbon atoms optionally substituted by one or two alkyl groups having 1 to 8 carbon atoms.
- the aromatic hydrocarbon structure with 6 carbon atoms is a benzene structure
- the aromatic hydrocarbon structure with 12 carbon atoms is a biphenyl structure.
- composition for an organic electroluminescence device of the present invention may contain only one of these iridium complexes, or may contain two or more of them.
- the charge-transporting material that may be contained as a functional material in the composition for an organic electroluminescent device of the present invention is a material having positive charge (hole) or negative charge (electron) transportability.
- the charge-transporting material is not particularly limited as long as it does not impair the effects of the present invention, and known materials can be applied.
- charge-transporting material a compound or the like conventionally used in the light-emitting layer of an organic electroluminescent device can be used.
- charge-transporting material a compound used as a host material for the light-emitting layer is particularly preferred.
- charge-transporting materials include aromatic amine-based compounds, phthalocyanine-based compounds, porphyrin-based compounds, oligothiophene-based compounds, polythiophene-based compounds, benzylphenyl-based compounds, and compounds in which a tertiary amine is linked with a fluorene group. , hydrazone-based compounds, silazane-based compounds, silanamine-based compounds, phosphamine-based compounds, and quinacridone-based compounds, which are exemplified as hole-transporting compounds for the hole injection layer 3 described later.
- electron-transporting compounds such as anthracene-based compounds, pyrene-based compounds, carbazole-based compounds, pyridine-based compounds, phenanthroline-based compounds, oxadiazole-based compounds, and silole-based compounds are included.
- charge-transporting materials include two or more condensed aromatic compounds containing two or more tertiary amines represented by 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl.
- Aromatic amines having a starburst structure such as aromatic diamines in which the ring is substituted by a nitrogen atom (JP-A-5-234681), 4,4′,4′′-tris(1-naphthylphenylamino)triphenylamine, etc. compound (J. Lumin., vol. 72-74, pp. 985, 1997), aromatic amine compound composed of triphenylamine tetramer (Chem.
- the charge-transporting material that may be contained in the composition for an organic electroluminescent device of the present invention is a repeating unit containing a structure represented by the following formula (3) (hereinafter sometimes referred to as "repeating unit (3)"). ) is preferable in terms of film formability.
- R 19 and R 20 are each independently an alkyl group having 1 to 20 carbon atoms, a (hetero)aralkyl group having 7 to 40 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, (hetero)aryloxy groups having 3 to 20 carbon atoms, alkylsilyl groups having 1 to 20 carbon atoms, arylsilyl groups having 6 to 20 carbon atoms, alkylcarbonyl groups having 2 to 20 carbon atoms, arylcarbonyl groups having 7 to 20 carbon atoms , an alkylamino group having 1 to 20 carbon atoms, an arylamino group having 6 to 20 carbon atoms, and a (hetero)aryl group having 3 to 30 carbon atoms, or a combination thereof. These groups may further have a substituent. ]
- R 19 and R 20 are each independently preferably an alkyl group having 1 to 20 carbon atoms or a (hetero)aralkyl group having 7 to 40 carbon atoms, from the viewpoint of solubility. From the viewpoint of heat resistance, R 19 and R 20 are each independently preferably a (hetero)aryl group having 3 to 30 carbon atoms.
- the repeating unit (3) which may be contained in the composition for an organic electroluminescent device of the present invention, the following formula is added in addition to the repeating unit (3) in that the charge transport property is enhanced. It preferably contains a repeating unit containing the structure represented by (3-1) (hereinafter sometimes referred to as “repeating unit (3-1)”). In this case, the repeating unit (3) may be included in the following repeating unit (3-1).
- Ar 21 to Ar 23 each independently represent a divalent (hetero)arylene group having 3 to 30 carbon atoms, which may have a substituent.
- Ar 24 and Ar 25 each independently represent an optionally substituted (hetero)aryl group having 3 to 30 carbon atoms.
- r represents an integer of 0 to 2;
- Ar 21 to Ar 23 are each independently a phenylene group, a biphenylene group, a terphenylene group, a fluorenediyl group, or any of these groups and having 30 or less carbon atoms linked together from the viewpoint of durability.
- a divalent group is preferred, and a p-phenylene group and a biphenylene group are particularly preferred. These groups may have a substituent.
- formula (3-1) includes a structure represented by formula (3), at least one selected from Ar 21 , Ar 22 , or at least one Ar 23 when r is 1 or more is represented by formula ( It is a fluorenyl group optionally having substituents at the 9 and 9′ positions represented by 3).
- Ar 24 and Ar 25 are each independently preferably a phenyl group, a biphenyl group, a terphenyl group, or a fluorenyl group, and particularly preferably a phenyl group or a fluorenyl group. These groups may have a substituent.
- the polymer compound having the repeating unit (3) which may be contained in the composition for an organic electroluminescent device of the present invention may contain only one type of the repeating unit (3), or may contain two or more types of the repeating unit (3). may be included. Further, it may contain only one type of the repeating unit (3-1), or may contain two or more types.
- the weight-average molecular weight (Mw) of the polymer compound having the repeating unit (3) which may be contained in the composition for organic electroluminescent elements of the present invention is usually 2,000,000 or less, preferably 500,000 or less. , more preferably 100,000 or less, still more preferably 50,000 or less, usually 2,500 or more, preferably 5,000 or more, more preferably 10,000 or more, still more preferably 20,000 or more. If the weight-average molecular weight is equal to or less than the above upper limit, excellent solubility in solvents and excellent film formability are obtained. If the weight average molecular weight is at least the above lower limit, the polymer compound has a high glass transition temperature, a high melting point and a high vaporization temperature, and is excellent in heat resistance.
- the number average molecular weight (Mn) of the polymer compound having the repeating unit (3) which may be contained in the composition for organic electroluminescent elements of the present invention is usually 1,000,000 or less, preferably 250,000 or less. , more preferably 50,000 or less, still more preferably 25,000 or less, usually 2,000 or more, preferably 4,000 or more, more preferably 8,000 or more, still more preferably 15,000 or more.
- the polydispersity (Mw/Mn) of the polymer compound having the repeating unit (3) which may be contained in the composition for organic electroluminescent elements of the present invention is preferably 3.5 or less, more preferably 2. 0.5 or less, particularly preferably 2.0 or less.
- the lower limit value is ideally 1 because the smaller the value of the degree of dispersion, the better.
- the weight average molecular weight of a polymer compound is determined by SEC (size exclusion chromatography) measurement.
- SEC size exclusion chromatography
- the weight average molecular weight is calculated by converting the elution time of the sample into molecular weight using a calibration curve calculated from the elution time of polystyrene (standard sample) with a known molecular weight.
- the number average molecular weight can also be obtained in the same manner.
- the method for producing the polymer compound having the repeating unit (3) which may be contained in the composition for an organic electroluminescent element of the present invention is not particularly limited, and the polymer compound having the repeating unit (3) can be obtained. optional as long as For example, it can be produced by a polymerization method by Suzuki reaction, a polymerization method by Grignard reaction, a polymerization method by Yamamoto reaction, a polymerization method by Ullmann reaction, a polymerization method by Buchwald-Hartwig reaction, or the like.
- composition for organic electroluminescence elements of the present invention contains a phenol derivative which is a compound represented by the following formula (1).
- a is an integer of 0 to 4.
- R 1 and R 2 each independently represent an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms.
- a is an integer of 2 to 4, multiple R 2 may be the same or different.
- the redox potential of the compound represented by formula (1) is negative due to the presence of an alkyl group or an alkoxy group, which are electron-donating groups, at the o-position of the hydroxy group. side, the HOMO becomes shallow, and itself becomes susceptible to oxidation. Therefore, oxidation of the functional material contained at the same time is suppressed.
- a is preferably 1 or 2 in terms of a moderate oxidation-reduction potential.
- R 1 and R 2 are alkyl groups having 1 to 12 carbon atoms are methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group, isopentyl group, hexyl group, cyclohexyl group, heptyl group, octyl group, 2-ethylhexyl group, nonyl group, decyl group, undecyl group and dodecyl group.
- R 1 and R 2 each being an alkoxy group having 1 to 12 carbon atoms are methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, s-butoxy and t-butoxy. , pentyloxy, isopentyloxy, hexyloxy, cyclohexyloxy, heptyloxy, octyloxy, 2-ethylhexyloxy, nonyloxy, decyloxy, undecyloxy and dodecyloxy.
- R 1 and R 2 are secondary or tertiary in that they have large steric hindrance, suppress the coupling reaction between phenoxy radicals generated after oxidation, and can function again as antioxidants.
- Alkyl groups are preferred, and tertiary alkyl groups are more preferred.
- the o-position of the hydroxyl group is preferably a t-butyl group, which is the smallest tertiary alkyl group, because it is inexpensive and because it has a small molecular weight, it does not easily remain in the light-emitting layer after film formation. .
- composition for organic electroluminescence elements of the present invention preferably contains a compound represented by the following formula (1-1) as the compound represented by formula (1).
- R 3 , R 4 and R 5 each independently represent an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms.
- b is an integer of 2 to 3
- multiple R 5 may be the same or different.
- b is preferably 0 or 1 in terms of a moderate oxidation-reduction potential.
- the o-position of the hydroxy group has a large steric hindrance, suppresses the coupling reaction between the phenoxy radicals generated after oxidation, and can function again as an antioxidant. are preferred, and tertiary alkyl groups are more preferred.
- the o-position of the hydroxyl group is preferably a t-butyl group, which is the smallest tertiary alkyl group, because it is inexpensive and because it has a small molecular weight, it does not easily remain in the light-emitting layer after film formation. . That is, the composition for organic electroluminescence elements of the present invention preferably contains a compound represented by the following formula (1-2) as the compound represented by formula (1).
- b is preferably 0 or 1 in terms of a moderate oxidation-reduction potential.
- composition for organic electroluminescent elements of the present invention contains an aliphatic ester solvent and/or an aromatic diester solvent having two or more carbonyl groups.
- the solvent contained in the composition for organic electroluminescent elements of the present invention is a volatile liquid component used for forming a layer containing a functional material by wet film formation.
- the solvent is preferably a solvent that satisfactorily dissolves the light-emitting material and the charge-transporting material, which are functional materials.
- An aliphatic ester solvent having two or more carbonyl groups has one or more carbonyl groups in addition to the carbonyl group contained in the aliphatic carboxylic acid ester moiety.
- the carbonyl group further possessed by the solvent may or may not be an aliphatic carboxylic acid ester group. This is preferable in that it is possible to further suppress changes in the liquid physical properties of the ink due to changes.
- carbonyl groups that are not aliphatic carboxylic acid ester groups include aromatic carboxylic acid ester groups, aliphatic carboxylic acid amide groups, aromatic carboxylic acid amide groups, ketone groups, and aldehyde groups. is preferable in that it can further suppress changes in the liquid physical properties of the ink due to structural changes due to oxidation of the phenol derivative.
- the aliphatic ester solvent having two or more carbonyl groups is preferably a compound having two ester groups in that it can further suppress changes in the liquid physical properties of the ink due to structural changes due to oxidation of the phenol derivative.
- a compound having one ester group and one ketone group is preferable in that the light-emitting material and the charge-transporting material, which are functional materials, are dissolved more satisfactorily.
- composition for organic electroluminescent elements of the present invention preferably contains a compound represented by the following formula (9-1) as an aliphatic dicarboxylic acid ester.
- R 24 represents an alkylene group.
- R 25 and R 26 each independently represent an alkyl group.
- R 24 and R 25 may combine with each other to form a ring.
- R 24 is preferably an alkylene group having 1 to 20 carbon atoms, more preferably an alkylene group having 2 to 12 carbon atoms, because it has appropriate volatility as a solvent.
- R 25 and R 26 are each independently preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, because they have appropriate volatility as a solvent.
- the alkylene group R 24 may be linear, branched, or cyclic.
- R 24 is preferably a straight-chain alkylene group in that the viscosity of the ink increases and the fluidity after application can be reduced.
- R 24 is preferably a branched alkylene group from the viewpoint of lowering the viscosity of the ink and stabilizing the ejection property during application by an inkjet method.
- R 24 is preferably a cyclic alkylene group from the viewpoint of lowering the viscosity of the ink and stabilizing the ejection property during application by an inkjet method.
- the alkyl groups R 25 and R 26 may be the same or different. Also, R 25 and R 26 may be linear, branched, or cyclic. R 25 and R 26 are preferably straight-chain alkyl groups in that the viscosity of the ink increases and the fluidity after application can be reduced. R 25 and R 26 are preferably branched alkyl groups from the viewpoint of lowering the viscosity of the ink and stabilizing the ejection property during application by an inkjet method. R 25 and R 26 are preferably cyclic alkyl groups from the viewpoint of lowering the viscosity of the ink and stabilizing the ejection property during application by an inkjet method.
- the compound represented by the formula (9-1) is preferably an aliphatic dicarboxylic acid ester containing a cyclic structure, in that the solute is easily dissolved and high-concentration ink is easily produced.
- composition for organic electroluminescent elements of the present invention preferably contains a compound represented by the following formula (9-2) as an aliphatic carboxylic acid ester having a ketone group.
- R 27 represents an alkylene group.
- R 28 and R 29 each independently represent an alkyl group.
- R 27 and R 28 or R 27 and R 29 may combine with each other to form a ring.
- R 27 is preferably an alkylene group having 1 to 20 carbon atoms, more preferably an alkylene group having 2 to 12 carbon atoms, because it has appropriate volatility as a solvent.
- R 28 and R 29 are each independently preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 6 carbon atoms, because they have appropriate volatility as a solvent.
- the alkylene group R 27 may be linear, branched, or cyclic.
- R 27 is preferably a straight-chain alkylene group because the viscosity of the ink increases and the fluidity after application can be reduced.
- R 27 is preferably a branched alkylene group from the viewpoint of lowering the viscosity of the ink and stabilizing the ejection property during application by an inkjet method.
- R 27 is preferably a cyclic alkylene group from the viewpoint of lowering the viscosity of the ink and stabilizing the ejection property during application by an inkjet method.
- the alkyl groups R 28 and R 29 may be the same or different. Also, R 28 and R 29 may be linear, branched, or cyclic. R 28 and R 29 are preferably straight-chain alkyl groups in that the viscosity of the ink increases and the fluidity after application can be reduced. R 28 and R 29 are preferably branched alkyl groups from the viewpoint of lowering the viscosity of the ink and stabilizing the ejection property during application by an inkjet method. R 28 and R 29 are preferably cyclic alkyl groups from the viewpoint of lowering the viscosity of the ink and stabilizing the ejection property during application by an inkjet method.
- the compound represented by the formula (9-2) is preferably an aliphatic carboxylic acid ester having a ketone group and containing a cyclic structure, in that the solute is easily dissolved and high-concentration ink is easily produced. preferable.
- aliphatic ester solvents having two or more carbonyl groups may be used singly, or two or more may be used in any combination and ratio.
- Aromatic diester solvents are preferable because they can effectively suppress changes in the liquid physical properties of the ink due to structural changes due to oxidation of the phenol derivative. Aromatic diester solvents are also preferred in that they can readily dissolve solutes.
- composition for organic electroluminescent elements of the present invention preferably contains a compound represented by the following formula (9-3) as an aromatic diether solvent.
- Ar 31 represents an arylene group
- R 30a and R 30b each independently represent an alkyl group.
- R 30a and Ar 31 may combine with each other to form a ring.
- Ar 31 is preferably a phenylene group or a naphthalenediyl group, and more preferably a phenylene group, since it has appropriate volatility as a solvent.
- Ar 31 is preferably an o-phenylene group or an m-phenylene group, and more preferably an m-phenylene group, in that the viscosity of the ink is lowered and the ejection property is stabilized when the ink is applied by an inkjet method.
- R 30a and R 30b are preferably alkyl groups having 1 to 20 carbon atoms, more preferably alkyl groups having 1 to 6 carbon atoms, because they have appropriate volatility as a solvent.
- the alkyl groups R 30a and R 30b may be the same or different. Moreover, R 30a and R 30b may be linear, branched, or cyclic. R 30a and R 30b are preferably straight-chain alkyl groups in that the viscosity of the ink increases and the fluidity after application can be reduced. R 30a and R 30b are preferably branched alkyl groups from the viewpoint of lowering the viscosity of the ink and stabilizing the ejection property during application by an inkjet method. R 30a and R 30b are preferably cyclic alkyl groups from the viewpoint of lowering the viscosity of the ink and stabilizing the ejection property during application by an inkjet method. R 30a and R 30b are preferably an alkyl group containing a cyclic structure in that the solute is easily dissolved and the preparation of high-concentration ink is facilitated.
- aromatic diester solvents may be used alone, or two or more types may be used in any combination and ratio.
- composition for an organic electroluminescent device of the present invention contains one or more of the aliphatic ester solvents having two or more carbonyl groups and one or more of the above aromatic diester solvents. , in any combination and ratio.
- composition for an organic electroluminescence device of the present invention may contain a solvent other than the aliphatic ester solvent having two or more carbonyl groups and the aromatic diester solvent.
- alkylated biphenyls As other solvents, alkylated biphenyls, aromatic ethers, and aromatic monoesters are preferable because they have moderate boiling points and easily dissolve solutes.
- the alkylated biphenyl that may be contained in the composition for an organic electroluminescent device of the present invention may be a monoalkylated biphenyl having one alkyl group or a dialkylated biphenyl having two alkyl groups.
- trialkylated biphenyl, tetraalkylated biphenyl, heptaalkylated biphenyl, hexaalkylated biphenyl, etc. having 3 or more alkyl groups may be used.
- Monoalkylated biphenyls or dialkylated biphenyls are preferable, and monoalkylated biphenyls are more preferable, because of their low boiling point and high volatility.
- Dialkylated biphenyls and trialkylated biphenyls are preferred, and trialkylated biphenyls are more preferred, in that they have a high melting point and are less likely to solidify when the composition is placed at a low temperature.
- Dialkylated biphenyls are preferred because they have moderate boiling and melting points.
- a monoalkylated biphenyl is represented by the following formula (4).
- R 31 represents an optionally substituted alkyl group.
- R 31 which is an alkyl group substituted for biphenyl, is preferably an alkyl group having 1 to 12 carbon atoms, examples of which include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and s-butyl groups. , t-butyl group, pentyl group, isopentyl group, hexyl group, cyclohexyl group, heptyl group, octyl group, 2-ethylhexyl group, nonyl group, decyl group, undecyl group and dodecyl group.
- R 31 may have a phenyl group as a substituent, and in this case, the alkyl group having a substituent is preferably a benzyl group or a 2-phenylethyl group.
- Monoalkylated biphenyls include, for example, 2-methylbiphenyl, 3-methylbiphenyl, 4-methylbiphenyl, 2-ethylbiphenyl, 3-ethylbiphenyl, 4-ethylbiphenyl, 2-propylbiphenyl, 3-propylbiphenyl, 4 -propylbiphenyl, 2-isopropylbiphenyl, 3-isopropylbiphenyl, 4-isopropylbiphenyl, 2-butylbiphenyl, 3-butylbiphenyl, 4-butylbiphenyl, 4-cyclohexylbiphenyl and the like.
- a dialkylated biphenyl is represented by the following formula (4-1) or (4-2).
- R 32 to R 35 each independently represent an optionally substituted alkyl group.
- R 32 to R 35 are the same as the preferred examples of R 31 .
- dialkylated biphenyl examples include 2,3-dimethylbiphenyl, 3,4-dimethylbiphenyl, 3,3′-dimethylbiphenyl, 2,4-diethylbiphenyl, 2,3′-diethylbiphenyl, 3,4′- Diethylbiphenyl, 2,2'-dipropylbiphenyl, 2,4-dipropylbiphenyl, 2,4'-dipropylbiphenyl, 3,4-diisopropylbiphenyl, 3,4'-diisopropylbiphenyl, 3,5-diisopropylbiphenyl , 3,3′-butylbiphenyl, 3,4′-butylbiphenyl, 4,4′-butylbiphenyl and the like.
- the trialkylated biphenyl is represented by the following formula (4-3) or (4-4).
- R 36 to R 41 each independently represent an optionally substituted alkyl group.
- R 32 to R 35 are the same as the preferred examples of R 31 .
- trialkylated biphenyl examples include 2,3,4-trimethylbiphenyl, 2,3,3'-trimethylbiphenyl, 3,3',4-trimethylbiphenyl, 2,4,4'-triethylbiphenyl, 3, 4,5-triethylbiphenyl, 3,4′,5-triethylbiphenyl, 2,2′,4-tripropylbiphenyl, 2,4,5-dipropylbiphenyl, 2,3,4′-tripropylbiphenyl, 2 ,3′,4-triisopropylbiphenyl, 2,3′,5-triisopropylbiphenyl, 3,4,4′-triisopropylbiphenyl and the like.
- alkylated biphenyls may be used alone, or two or more types may be used in any combination and ratio.
- aromatic ethers that may be contained in the composition for organic electroluminescent elements of the present invention may have an alkyl group represented by the following formula (5) in terms of having high solubility. Alkoxybenzenes are preferred.
- i represents an integer of 0 to 5.
- R 51 and R 52 each independently represent an optionally substituted alkyl group.
- i has a low boiling point and high volatility, it is preferably an integer of 0 to 3, more preferably 0 or 1.
- R 51 and R 52 are preferably alkyl groups having 1 to 12 carbon atoms, examples of which include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl and t-butyl groups. , pentyl group, isopentyl group, hexyl group, cyclohexyl group, heptyl group, octyl group, 2-ethylhexyl group, nonyl group, decyl group, undecyl group and dodecyl group.
- R 51 and R 52 may have a phenyl group as a substituent, and in this case, a benzyl group and a 2-phenylethyl group are preferable as the alkyl group having a substituent.
- j and k represent integers of 0 to 5.
- R 53 and R 54 each independently represent an optionally substituted alkyl group.
- j and k have a low boiling point and high volatility, they are preferably integers of 0 to 2, more preferably 0 or 1.
- R 53 and R 54 are preferably alkyl groups having 1 to 12 carbon atoms, examples of which include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl and t-butyl groups. , pentyl group, isopentyl group, hexyl group, cyclohexyl group, heptyl group, octyl group, 2-ethylhexyl group, nonyl group, decyl group, undecyl group and dodecyl group.
- R 53 and R 54 may have a phenyl group as a substituent, and in this case, a benzyl group and a 2-phenylethyl group are preferable as the alkyl group having a substituent.
- the aromatic monoester that may be contained in the composition for organic electroluminescent elements of the present invention is preferably a benzoic acid monoester that may have an alkyl group represented by the following formula (6).
- q represents an integer of 0 to 5.
- R 55 and R 56 each independently represent an optionally substituted alkyl group.
- q has a low boiling point and high volatility, it is preferably an integer of 0 to 2, more preferably 0 or 1.
- R 55 and R 56 are preferably alkyl groups having 1 to 12 carbon atoms, examples of which include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, s-butyl and t-butyl groups. , pentyl group, isopentyl group, hexyl group, cyclohexyl group, heptyl group, octyl group, 2-ethylhexyl group, nonyl group, decyl group, undecyl group and dodecyl group.
- R 55 and R 56 may have a phenyl group as a substituent, and in this case, a benzyl group and a 2-phenylethyl group are preferable as the alkyl group having a substituent.
- aromatic ethers and/or aromatic monoesters may be used singly, or two or more of them may be used in any combination and ratio. That is, only one aromatic ether may be used, or only one aromatic monoester may be used, and one or more aromatic ethers and one or two aromatic monoesters may be used. More than one species may be used in any combination and ratio.
- a solvent other than the aliphatic ester solvent and the aromatic diester solvent having two or more carbonyl groups other than the alkylated biphenyls, aromatic ethers, and aromatic monoesters may contain other solvents.
- alkylated biphenyls examples include alkanes such as n-decane, cyclohexane, ethylcyclohexane, decalin, and bicyclohexane; toluene, xylene, mesitylene, and cyclohexyl.
- aromatic hydrocarbons such as benzene (phenylcyclohexane) and tetralin; halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene and trichlorobenzene; alicyclic ketones such as cyclohexanone, cyclooctanone and fenchone; Alicyclic alcohols such as cyclooctanol; aliphatic ketones such as methyl ethyl ketone and dibutyl ketone; aliphatic alcohols such as butanol and hexanol; ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol-1-monomethyl ether acetate ( PGMEA) and other aliphatic ethers.
- PGMEA propylene glycol-1-monomethyl ether acetate
- the boiling point of the solvent is usually 80°C or higher, preferably 100°C or higher, more preferably 150°C or higher, particularly preferably 200°C or higher, and usually 350°C or lower, preferably 320°C or lower, more preferably 300°C or lower. be. If the boiling point is below this range, the film formation stability may decrease due to solvent evaporation from the composition during wet film formation.
- the content (concentration) of the light-emitting material in the composition for organic electroluminescent elements of the present invention is preferably 0.05% by mass. Above, more preferably 0.1% by mass or more, still more preferably 0.2% by mass or more, preferably 8.0% by mass or less, more preferably 4.0% by mass or less, still more preferably 2.0% by mass It is below. If the concentration of the luminescent material is equal to or higher than the above lower limit, a layer containing a sufficient amount of the luminescent material can be formed. If the concentration of the light-emitting material is equal to or less than the above upper limit, it is easy to maintain a uniform state without precipitating the dissolved light-emitting material.
- the content (concentration) of the charge-transporting material in the composition for organic electroluminescent elements of the present invention is preferably 0. .1% by mass or more, more preferably 0.2% by mass or more, still more preferably 0.4% by mass or more, preferably 16% by mass or less, more preferably 8.0% by mass or less, still more preferably 4.0% by mass % by mass or less. If the concentration of the charge-transporting material is at least the above lower limit, a layer containing a sufficient amount of the charge-transporting material can be formed. If the concentration of the charge-transporting material is equal to or less than the above upper limit, it is easy to maintain a uniform state without precipitating the dissolved charge-transporting material.
- the total content (concentration) of these in the composition for organic electroluminescent elements of the present invention is preferably is 0.1% by mass or more, more preferably 0.2% by mass or more, more preferably 0.4% by mass or more, preferably 16% by mass or less, more preferably 8.0% by mass or less, further preferably 4 0% by mass or less. If the total concentration of the functional material is equal to or higher than the above lower limit, a layer containing sufficient functional material can be formed. If the total concentration of the functional material is equal to or less than the above upper limit, it is easy to maintain a uniform state without precipitating the dissolved functional material.
- the content (concentration) of the phenol derivative, which is the compound represented by the formula (1), contained in the composition for an organic electroluminescent device of the present invention is preferably 5 mass ppm or more, more preferably 10 mass ppm or more, More preferably 20 mass ppm or more, preferably 4000 mass ppm or less, more preferably 2000 mass ppm or less, still more preferably 1000 mass ppm or less. If the concentration of the phenol derivative is equal to or higher than the above lower limit, the effect of suppressing deterioration of the functional material by the phenol derivative can be sufficiently obtained. If the concentration of the phenol derivative is equal to or less than the above upper limit, it is easy to remove the phenol derivative and its oxide together with the solvent when forming the light-emitting layer.
- the content of the aliphatic ester solvent and/or the aromatic diester solvent having two or more carbonyl groups contained in the composition for an organic electroluminescent device of the present invention is preferably 2.0% by mass or more, more preferably 5.0% by mass or more. It is 0% by mass or more, more preferably 10% by mass or more. If the content of the aliphatic ester solvent having two or more carbonyl groups and/or the aromatic diester solvent is at least the above lower limit, changes in liquid properties during long-term storage of the ink can be reduced.
- composition for an organic electroluminescent element of the present invention may further contain the above-mentioned other solvent in addition to the above-mentioned aliphatic ester solvent and/or aromatic diester solvent having two or more carbonyl groups.
- the content of the other solvents in the total solvent is an aliphatic ester solvent and / or an aromatic diester solvent having two or more carbonyl groups
- it is preferably 95% by mass or less, particularly 85% by mass or less.
- the total content of the solvent in the composition for an organic electroluminescence device of the present invention is preferably large in terms of ease of film formation due to its low viscosity, while it is small in terms of ease of forming a thick film. is preferred.
- the total solvent content of the composition for organic electroluminescent elements of the present invention is preferably 1% by mass or more, more preferably 10% by mass or more, particularly preferably 50% by mass or more, and preferably 99.99% by mass. % or less, more preferably 99.9 mass % or less, particularly preferably 99 mass % or less.
- composition for an organic electroluminescent element of the present invention is particularly suitable for use as a composition for forming a light-emitting layer containing a light-emitting material and a charge-transporting material as functional materials.
- Organic electroluminescent device has a light-emitting layer formed using the composition for organic electroluminescent devices of the present invention.
- the organic electroluminescent device of the present invention preferably has on a substrate at least an anode, a cathode, and at least one organic layer between the anode and the cathode, wherein at least one of the organic layers is It is a light-emitting layer formed by a wet film-forming method using the composition for an organic electroluminescent element of the present invention.
- the wet film formation method means a film formation method, that is, a coating method, such as a spin coating method, a dip coating method, a die coating method, a bar coating method, a blade coating method, a roll coating method, a spray coating method, a capillary
- a coating method such as a spin coating method, a dip coating method, a die coating method, a bar coating method, a blade coating method, a roll coating method, a spray coating method, a capillary
- a wet film forming method such as a coating method, an inkjet method, a nozzle printing method, a screen printing method, a gravure printing method, or a flexographic printing method is used, and the film formed by these methods is dried to form a film.
- a coating method such as a spin coating method, a dip coating method, a die coating method, a bar coating method, a blade coating method, a roll coating method, a spray coating method, a capillary
- FIG. 1 is a schematic cross-sectional view showing a structural example suitable for the organic electroluminescence device 10 of the present invention.
- reference numeral 1 denotes a substrate, 2 an anode, 3 a hole injection layer, 4 a hole transport layer, 5 a light emitting layer, 6 a hole blocking layer, and 7 an electron transport layer.
- 8 denotes an electron injection layer
- 9 denotes a cathode.
- the substrate 1 serves as a support for the organic electroluminescence element, and is usually made of a quartz or glass plate, a metal plate or metal foil, a plastic film or sheet, or the like. Among these, glass plates and transparent synthetic resin plates such as polyester, polymethacrylate, polycarbonate and polysulfone are preferred.
- the substrate 1 is preferably made of a material having a high gas barrier property because deterioration of the organic electroluminescence element due to outside air is unlikely to occur. Therefore, especially when using a material having low gas barrier properties such as a synthetic resin substrate, it is preferable to provide a dense silicon oxide film or the like on at least one side of the substrate 1 to improve the gas barrier properties.
- the anode 2 has the function of injecting holes into the layer on the light-emitting layer side.
- the anode 2 is generally made of metals such as aluminum, gold, silver, nickel, palladium, platinum; metal oxides such as indium and/or tin oxides; metal halides such as copper iodide; carbon black or poly(3 -methylthiophene), polypyrrole, and polyaniline.
- the formation of the anode 2 is usually carried out by dry methods such as sputtering and vacuum deposition.
- metal fine particles such as silver, fine particles such as copper iodide, carbon black, conductive metal oxide fine particles, conductive polymer fine powder, etc.
- they are dispersed in an appropriate binder resin solution.
- It can also be formed by coating on a substrate.
- a conductive polymer a thin film can be formed directly on the substrate by electrolytic polymerization, or the conductive polymer can be applied onto the substrate to form the anode 2 (Appl. Phys. Lett., Vol. 60). , 2711, 1992).
- the anode 2 usually has a single-layer structure, but may have a laminated structure as appropriate. When the anode 2 has a laminated structure, different conductive materials may be laminated on the first layer of the anode.
- the thickness of the anode 2 may be determined according to the required transparency and material. When particularly high transparency is required, the thickness is preferably such that the visible light transmittance is 60% or more, more preferably 80% or more.
- the thickness of the anode 2 is usually 5 nm or more, preferably 10 nm or more, and usually 1000 nm or less, preferably 500 nm or less. If transparency is not required, the thickness of the anode 2 may be arbitrarily set according to the required strength, etc. In this case, the anode 2 may have the same thickness as the substrate 1 .
- a layer that functions to transport holes from the anode 2 side to the light emitting layer 5 side is usually called a hole injection transport layer or a hole transport layer.
- the layer closer to the anode 2 side may be called the hole injection layer 3 .
- the hole injection layer 3 is preferably used from the viewpoint of enhancing the function of transporting holes from the anode 2 to the light emitting layer 5 side.
- the hole injection layer 3 is usually formed on the anode 2 .
- the film thickness of the hole injection layer 3 is usually 1 nm or more, preferably 5 nm or more, and usually 1000 nm or less, preferably 500 nm or less.
- the method for forming the hole injection layer 3 may be a vacuum deposition method or a wet film formation method. From the viewpoint of excellent film-forming properties, it is preferable to form the film by a wet film-forming method.
- the hole injection layer 3 preferably contains a hole-transporting compound, and more preferably contains a hole-transporting compound and an electron-accepting compound. Furthermore, the hole injection layer 3 preferably contains a cation radical compound, and particularly preferably contains a cation radical compound and a hole-transporting compound.
- the hole injection layer-forming composition usually contains a hole-transporting compound that forms the hole injection layer 3 . Moreover, in the case of a wet film-forming method, it usually contains a solvent.
- the hole-transporting compound preferably has a high hole-transporting property and can efficiently transport injected holes. For this reason, it is preferable that the hole-transporting compound has a high hole mobility and that impurities that act as traps are less likely to be generated during manufacture, use, or the like. Further, the hole-transporting compound preferably has excellent stability, low ionization potential, and high transparency to visible light.
- the hole injection layer 3 when the hole injection layer 3 is in contact with the light-emitting layer 5, it is preferable to use a material that does not quench light emitted from the light-emitting layer 5 or that forms an exciplex with the light-emitting layer 5 so as not to lower the light emission efficiency.
- hole transport compound a compound having an ionization potential of 4.5 eV to 6.0 eV is preferable as the hole transport compound.
- hole-transporting compounds include aromatic amine-based compounds, phthalocyanine-based compounds, porphyrin-based compounds, oligothiophene-based compounds, polythiophene-based compounds, benzylphenyl-based compounds, compounds in which tertiary amines are linked with fluorene groups, and hydrazones. compounds, silazane compounds, quinacridone compounds, and the like.
- aromatic amine compounds are preferred, and aromatic tertiary amine compounds are particularly preferred, in terms of amorphousness and visible light transparency.
- the aromatic tertiary amine compound is a compound having an aromatic tertiary amine structure, and includes a compound having a group derived from an aromatic tertiary amine.
- the type of the aromatic tertiary amine compound is not particularly limited, but a polymer compound having a weight average molecular weight of 1,000 or more and 1,000,000 or less (repeating unit is preferably used.
- Preferred examples of aromatic tertiary amine polymer compounds include polymer compounds having repeating units represented by the following formula (I).
- Ar 1 and Ar 2 each independently represent an optionally substituted aromatic group or an optionally substituted heteroaromatic group.
- Ar 3 to Ar 5 each independently represent an optionally substituted aromatic group or an optionally substituted heteroaromatic group.
- Q represents a linking group selected from the following linking group group. Two groups of Ar 1 to Ar 5 that are bonded to the same N atom may be bonded to each other to form a ring.
- the linking groups are shown below.
- Ar 6 to Ar 16 each independently represent an optionally substituted aromatic group or an optionally substituted heteroaromatic group.
- R a to R b each independently represent a hydrogen atom or any substituent.
- the aromatic group and heteroaromatic group of Ar 1 to Ar 16 are benzene ring, naphthalene ring, phenanthrene ring, thiophene ring and pyridine ring from the viewpoint of solubility, heat resistance and hole injection transport property of the polymer compound. derived groups are preferred, and groups derived from a benzene ring or a naphthalene ring are more preferred.
- aromatic tertiary amine polymer compounds having repeating units represented by formula (I) include those described in International Publication No. 2005/089024 pamphlet.
- the hole injection layer 3 preferably contains an electron-accepting compound because the conductivity of the hole injection layer 3 can be improved by oxidation of the hole-transporting compound.
- the electron-accepting compound a compound having oxidizing power and the ability to accept one electron from the above-mentioned hole-transporting compound is preferable.
- the electron-accepting compound is preferably a compound having an electron affinity of 4 eV or more, and more preferably a compound having an electron affinity of 5 eV or more.
- electron-accepting compounds include triarylboron compounds, metal halides, Lewis acids, organic acids, onium salts, salts of arylamines and metal halides, and salts of arylamines and Lewis acids.
- triarylboron compounds include triarylboron compounds, metal halides, Lewis acids, organic acids, onium salts, salts of arylamines and metal halides, and salts of arylamines and Lewis acids.
- metal halides include triarylboron compounds, metal halides, Lewis acids, organic acids, onium salts, salts of arylamines and metal halides, and salts of arylamines and Lewis acids.
- salts of arylamines and Lewis acids include triarylboron compounds, metal halides, Lewis acids, organic acids, onium salts, salts of arylamines and metal halides, and salts of arylamines and Lewis acids.
- One or two or more compounds selected from the group are included.
- onium salts substituted with organic groups such as 4-isopropyl-4′-methyldiphenyliodonium tetrakis(pentafluorophenyl)borate, triphenylsulfonium tetrafluoroborate (WO 2005/089024); High-valence inorganic compounds such as iron (III) (JP-A-11-251067) and ammonium peroxodisulfate; cyano compounds such as tetracyanoethylene; tris(pentafluorophenyl)borane (JP-A-2003-31365) aromatic boron compounds such as; fullerene derivatives and iodine;
- organic groups such as 4-isopropyl-4′-methyldiphenyliodonium tetrakis(pentafluorophenyl)borate, triphenylsulfonium tetrafluoroborate (WO 2005/089024);
- High-valence inorganic compounds such as iron
- the cation radical compound is preferably an ionic compound composed of a cation radical, which is a chemical species obtained by removing one electron from a hole-transporting compound, and a counter anion.
- a cation radical which is a chemical species obtained by removing one electron from a hole-transporting compound, and a counter anion.
- 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 is removed from the repeating unit of the polymer compound.
- the cation radical is preferably a chemical species obtained by removing one electron from the compound described above as a hole-transporting compound. From the viewpoints of amorphousness, visible light transmittance, heat resistance, solubility, and the like, chemical species obtained by removing one electron from a compound that is preferable as a hole-transporting compound is preferable.
- the cation radical compound can be produced by mixing the hole-transporting compound and the electron-accepting compound described above. That is, by mixing the hole-transporting compound and the electron-accepting compound described above, electron transfer occurs from the hole-transporting compound to the electron-accepting compound, and the cation radical of the hole-transporting compound and the counter anion A cationic compound consisting of is generated.
- Cation radical compounds derived from polymer compounds such as PEDOT/PSS (Adv. Mater., 2000, vol. 12, pp. 481) and emeraldine hydrochloride (J. Phys. Chem., 1990, vol. 94, pp. 7716) is also produced by oxidation polymerization (dehydrogenation polymerization).
- the oxidative polymerization as used herein is chemically or electrochemically oxidizing a monomer in an acidic solution using peroxodisulfate or the like.
- the monomer is polymerized by oxidation, and a cation radical obtained by removing one electron from the repeating unit of the polymer with an anion derived from an acidic solution as a counter anion is generated. Generate.
- a material for the hole injection layer 3 is mixed with a soluble solvent (solvent for the hole injection layer) to form a film-forming composition (positive A composition for forming a hole injection layer) is prepared, and this composition for forming a hole injection layer is formed on a layer corresponding to the lower layer of the hole injection layer 3 (usually, the anode 2) by a wet film formation method. , formed by drying. Drying of the deposited film can be performed in the same manner as the drying method in the formation of the light-emitting layer 5 by the wet film-forming method described below.
- the concentration of the hole-transporting compound in the hole-injection layer-forming composition is arbitrary as long as it does not significantly impair the effects of the present invention. A higher value is preferable from the viewpoint that defects are less likely to occur in the layer 3 .
- the concentration of the hole-transporting compound in the composition for forming a hole injection layer is preferably 0.01% by mass or more, more preferably 0.1% by mass or more. It is particularly preferably 5% by mass or more, preferably 70% by mass or less, further preferably 60% by mass or less, and particularly preferably 50% by mass or less.
- solvents examples include ether-based solvents, ester-based solvents, aromatic hydrocarbon-based solvents, and amide-based solvents.
- ether-based solvents include aliphatic ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol-1-monomethyl ether acetate (PGMEA), 1,2-dimethoxybenzene, 1,3-dimethoxybenzene, and anisole. , phenetole, 2-methoxytoluene, 3-methoxytoluene, 4-methoxytoluene, 2,3-dimethylanisole and 2,4-dimethylanisole.
- aliphatic ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol-1-monomethyl ether acetate (PGMEA), 1,2-dimethoxybenzene, 1,3-dimethoxybenzene, and anisole.
- PGMEA propylene glycol-1-monomethyl ether acetate
- 1,2-dimethoxybenzene 1,3-dimethoxybenzen
- ester-based solvents include aromatic esters such as phenyl acetate, phenyl propionate, methyl benzoate, ethyl benzoate, propyl benzoate and n-butyl benzoate.
- aromatic hydrocarbon solvents include toluene, xylene, cyclohexylbenzene, 3-isopropylbiphenyl, 1,2,3,4-tetramethylbenzene, 1,4-diisopropylbenzene and methylnaphthalene.
- amide solvents examples include N,N-dimethylformamide and N,N-dimethylacetamide. In addition to these, dimethyl sulfoxide and the like can also be used.
- Formation of the hole injection layer 3 by a wet film-forming method is usually carried out by preparing a composition for forming a hole injection layer and then applying it on a layer corresponding to the lower layer of the hole injection layer 3 (usually the anode 2). It is carried out by coating and forming a film on the surface and drying it. After forming the hole injection layer 3, the coating film is usually dried by heating, drying under reduced pressure, or the like.
- the hole injection layer 3 is formed by a vacuum deposition method
- one or more of the constituent materials of the hole injection layer 3 are usually vacuum-evaporated.
- a crucible installed in a container when using two or more kinds of materials, usually put them in separate crucibles, evacuate the inside of the vacuum container to about 10 -4 Pa with a vacuum pump, and then heat the crucible.
- the degree of vacuum during vapor deposition is not limited as long as it does not significantly impair the effects of the present invention. 12.0 ⁇ 10 ⁇ 4 Pa) or less.
- the vapor deposition rate is not limited as long as it does not significantly impair the effects of the present invention, but is usually 0.1 ⁇ /second or more and 5.0 ⁇ /second or less.
- the film formation temperature during vapor deposition is not particularly limited as long as the effects of the present invention are not significantly impaired, but is preferably 10° C. or higher and 50° C. or lower.
- the hole transport layer 4 is a layer that functions to transport holes from the anode 2 side to the light emitting layer 5 side.
- the hole-transporting layer 4 is not an essential layer in the organic electroluminescent device of the present invention, but is preferably provided in terms of enhancing the function of transporting holes from the anode 2 to the light-emitting layer 5 .
- the hole transport layer 4 is usually formed between the anode 2 and the light emitting layer 5 .
- the hole transport layer 4 is formed between the hole injection layer 3 and the light emitting layer 5 when the hole injection layer 3 described above is present.
- the film thickness of the hole transport layer 4 is usually 5 nm or more, preferably 10 nm or more, and usually 300 nm or less, preferably 100 nm or less.
- the method for forming the hole transport layer 4 may be a vacuum deposition method or a wet film formation method. From the viewpoint of excellent film-forming properties, it is preferable to form the film by a wet film-forming method.
- the hole-transporting layer 4 usually contains a hole-transporting compound that becomes the hole-transporting layer 4 .
- a hole-transporting compound contained in the hole-transporting layer 4 two or more tertiary Aromatic diamines containing amines in which two or more condensed aromatic rings are substituted on the nitrogen atom (JP-A-5-234681), 4,4′,4′′-tris(1-naphthylphenylamino)triphenylamine, etc. (J. Lumin., Vol. 72-74, pp. 985, 1997), an aromatic amine compound composed of a tetramer of triphenylamine (Chem. Commun., pp.
- spiro compounds such as 2,2′,7,7′-tetrakis-(diphenylamino)-9,9′-spirobifluorene (Synth. Metals, 91, 209, 1997), 4, Examples include carbazole derivatives such as 4'-N,N'-dicarbazole biphenyl, etc.
- the composition for forming a hole transport layer usually further contains a solvent.
- a solvent used for the composition for forming the hole transport layer, the same solvents as those used for the composition for forming the hole injection layer can be used.
- the concentration of the hole-transporting compound in the hole-transporting layer-forming composition can be in the same range as the concentration of the hole-transporting compound in the hole-injection layer-forming composition.
- a positive hole-injection layer 3 is usually used instead of the constituent material of the hole-injection layer 3 in the same manner as in the case of forming the hole-injection layer 3 by vacuum deposition. It can be formed using the constituent material of the hole transport layer 4 . Film formation conditions such as degree of vacuum, vapor deposition rate and temperature during vapor deposition can be the same as those for the vacuum vapor deposition of the hole injection layer 3 .
- the light-emitting layer 5 is a layer that functions to emit light by being excited by recombination of holes injected from the anode 2 and electrons injected from the cathode 9 when an electric field is applied between a pair of electrodes. .
- the light-emitting layer 5 is a layer formed between the anode 2 and the cathode 9, and the light-emitting layer 5 is formed between the hole-injection layer 3 and the cathode 9 when the hole-injection layer 3 is on the anode 2. and between the hole-transport layer 4 and the cathode 9, if there is a hole-transport layer 4 on the anode 2;
- the film thickness of the light-emitting layer 5 is arbitrary as long as it does not significantly impair the effects of the present invention, but a thicker one is preferable from the viewpoint that defects are less likely to occur in the film, while a thinner one is preferable from the viewpoint that a low driving voltage can be easily achieved.
- the thickness of the light-emitting layer 5 is preferably 3 nm or more, more preferably 5 nm or more, usually 200 nm or less, and more preferably 100 nm or less.
- the light-emitting layer 5 contains at least a material having light-emitting properties (light-emitting material) and preferably contains a material having charge-transporting properties (charge-transporting material).
- a general luminescent material and a method for forming a luminescent layer will be described below. It is preferably formed by As the light-emitting material, an iridium complex, which is an organometallic complex containing iridium as a central element, is preferable, but other light-emitting materials may be used as appropriate. Light-emitting materials other than the iridium complex compound will be described in detail below.
- the luminescent material is not particularly limited as long as it emits light at a desired emission wavelength and does not impair the effects of the present invention, and known luminescent materials can be applied.
- the light-emitting material may be a fluorescent light-emitting material or a phosphorescent light-emitting material, but a material with good light emission efficiency is preferable, and a phosphorescent light-emitting material is preferable from the viewpoint of internal quantum efficiency.
- fluorescent materials include the following materials.
- Fluorescent materials that emit blue light include, for example, naphthalene, perylene, pyrene, anthracene, coumarin, chrysene, p-bis(2-phenylethenyl)benzene and derivatives thereof.
- Fluorescent materials that emit green light include, for example, quinacridone derivatives, coumarin derivatives, and aluminum complexes such as Al(C 9 H 6 NO) 3 .
- Examples of fluorescent light-emitting materials that emit yellow light include rubrene and perimidone derivatives.
- fluorescent light-emitting materials examples include DCM (4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran) compounds, benzopyran derivatives, and rhodamine derivatives. , benzothioxanthene derivatives, azabenzothioxanthene and the like.
- phosphorescent materials for example, from Groups 7 to 11 of the long period periodic table (hereinafter, unless otherwise specified, the term "periodic table” refers to the long period periodic table.)
- Organometallic complexes containing selected metals and the like can be mentioned.
- Metals selected from Groups 7 to 11 of the periodic table are preferably ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum, and gold.
- a ligand in which a (hetero)aryl group such as a (hetero)arylpyridine ligand and a (hetero)arylpyrazole ligand is linked to pyridine, pyrazole, phenanthroline, or the like is preferable. Phenylpyridine ligands and phenylpyrazole ligands are particularly preferred.
- (hetero)aryl represents an aryl group or a heteroaryl group.
- Preferable phosphorescent materials specifically include tris(2-phenylpyridine)iridium, tris(2-phenylpyridine)ruthenium, tris(2-phenylpyridine)palladium, bis(2-phenylpyridine)platinum, tris(2 -phenylpyridine)osmium, tris(2-phenylpyridine)rhenium and other phenylpyridine complexes, octaethylplatinum porphyrin, octaphenylplatinum porphyrin, octaethylpalladium porphyrin, octaphenylpalladium porphyrin and other porphyrin complexes.
- Polymer-based luminescent materials include poly(9,9-dioctylfluorene-2,7-diyl), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(4,4′- (N-(4-sec-butylphenyl))diphenylamine)], poly[(9,9-dioctylfluorene-2,7-diyl)-co-(1,4-benzo-2 ⁇ 2,1′-3 ⁇ -triazole)] and polyphenylene vinylene materials such as poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylene vinylene].
- the charge-transporting material is a material having positive charge (hole) or negative charge (electron) transportability, and is not particularly limited as long as it does not impair the effects of the present invention, and known materials can be applied.
- As the charge-transporting material a compound conventionally used in the light-emitting layer 5 of an organic electroluminescent element can be used, and a compound used as a host material of the light-emitting layer 5 is particularly preferable.
- charge-transporting materials include aromatic amine-based compounds, phthalocyanine-based compounds, porphyrin-based compounds, oligothiophene-based compounds, polythiophene-based compounds, benzylphenyl-based compounds, and compounds in which a tertiary amine is linked with a fluorene group. , hydrazone-based compounds, silazane-based compounds, silanamine-based compounds, phosphamine-based compounds, and quinacridone-based compounds, which are exemplified as hole-transporting compounds for the hole injection layer 3 .
- electron-transporting compounds such as anthracene-based compounds, pyrene-based compounds, carbazole-based compounds, pyridine-based compounds, phenanthroline-based compounds, oxadiazole-based compounds, and silole-based compounds are included.
- the charge-transporting material includes, for example, 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl containing two or more tertiary amines and two or more condensed Aromatics having a starburst structure such as aromatic diamines in which the aromatic ring is substituted on the nitrogen atom (JP-A-5-234681), 4,4′,4′′-tris(1-naphthylphenylamino)triphenylamine, etc. Amine compounds (J. Lumin., 72-74, 985, 1997), aromatic amine compounds composed of triphenylamine tetramer (Chem.
- Oxadiazole compounds such as 2,5-bis(6′-(2′,2′′-bipyridyl))-1,1-dimethyl-3,4-diphenylsilole (PyPySPyPy), bathophenanthroline ( BPhen), 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP, bathocuproine) and other phenanthroline compounds.
- the method for forming the light-emitting layer 5 may be either a vacuum deposition method or a wet film formation method, but the wet film formation method is preferred because of its excellent film formability.
- a light-emitting A material for layer 5 is mixed with a soluble solvent (solvent for light-emitting layer) to prepare a light-emitting layer-forming composition.
- a soluble solvent solvent for light-emitting layer
- the solvent examples include ether-based solvents, ester-based solvents, aromatic hydrocarbon-based solvents, amide-based solvents, alkane-based solvents, halogenated aromatic hydrocarbon-based solvents, aliphatic group alcohol solvents, alicyclic alcohol solvents, aliphatic ketone solvents, alicyclic ketone solvents and the like.
- Preferred solvents are as exemplified as aliphatic ester solvents having two or more carbonyl groups, aromatic diester solvents, and other solvents contained in the composition for organic electroluminescence devices of the present invention.
- the amount of solvent used is arbitrary as long as it does not significantly impair the effects of the present invention.
- the total content in the composition for forming a light-emitting layer is preferably as high as possible in terms of ease of film formation due to its low viscosity, and as low as possible in terms of ease of forming a thick film.
- the content of the solvent in the light-emitting layer-forming composition is preferably 1% by mass or more, more preferably 10% by mass or more, particularly preferably 50% by mass or more, and preferably 99.99% by mass or less. , more preferably 99.9% by mass or less, particularly preferably 99% by mass or less.
- Heating or pressure reduction can be used as a method for removing the solvent after wet film formation.
- a clean oven and a hot plate are preferable because they uniformly apply heat to the entire film.
- the heating temperature in the heating step is arbitrary as long as it does not significantly impair the effects of the present invention, but a higher temperature is preferable in terms of shortening the drying time, and a lower temperature is preferable in terms of less damage to the material.
- the upper limit of the heating temperature is usually 250°C or lower, preferably 200°C or lower, more preferably 150°C or lower.
- the lower limit of the heating temperature is usually 30°C or higher, preferably 50°C or higher, and more preferably 80°C or higher.
- a temperature exceeding the above upper limit is not preferable because the heat resistance is higher than that of the charge-transporting material or the phosphorescent material that is commonly used, and decomposition or crystallization may occur.
- a temperature lower than the above lower limit is not preferred because it takes a long time to remove the solvent.
- the heating time in the heating step is appropriately determined according to the boiling point and vapor pressure of the solvent in the light-emitting layer-forming composition, the heat resistance of the material, and the heating conditions.
- the light-emitting layer 5 is formed by a vacuum deposition method
- one or two constituent materials of the light-emitting layer 5 are usually used. Put more than one kind in a crucible installed in a vacuum container (when using two or more kinds of materials, usually put them in separate crucibles), and after evacuating the inside of the vacuum container to about 10 -4 Pa with a vacuum pump.
- the light-emitting layer 5 is formed on the hole-injecting layer 3 or the hole-transporting layer 4 placed facing each other in the crucible.
- the light-emitting layer 5 can also be formed by putting a mixture of them in a crucible, heating and evaporating them.
- the degree of vacuum during vapor deposition is not limited as long as it does not significantly impair the effects of the present invention. 12.0 ⁇ 10 ⁇ 4 Pa) or less.
- the vapor deposition rate is not limited as long as it does not significantly impair the effects of the present invention, but is usually 0.1 ⁇ /second or more and 5.0 ⁇ /second or less.
- the film formation temperature during vapor deposition is not particularly limited as long as the effects of the present invention are not significantly impaired, but is preferably 10° C. or higher and 50° C. or lower.
- a hole blocking layer 6 may be provided between the light emitting layer 5 and an electron injection layer 8 which will be described later.
- the hole blocking layer 6 is a layer laminated on the light emitting layer 5 so as to be in contact with the interface of the light emitting layer 5 on the cathode 9 side.
- the hole-blocking layer 6 has a role of blocking holes moving from the anode 2 from reaching the cathode 9 and a role of efficiently transporting electrons injected from the cathode 9 toward the light-emitting layer 5.
- Physical properties required for the material constituting the hole blocking layer 6 include high electron mobility and low hole mobility, a large energy gap (difference between HOMO and LUMO), and an excited triplet level (T1). is high.
- Examples of materials for the hole blocking layer 6 satisfying these conditions include bis(2-methyl-8-quinolinolato)(phenolato)aluminum and bis(2-methyl-8-quinolinolato)(triphenylsilanolate)aluminum.
- mixed ligand complexes such as bis(2-methyl-8-quinolato)aluminum- ⁇ -oxo-bis-(2-methyl-8-quinolinolato)aluminum dinuclear metal complexes such as metal complexes, distyrylbiphenyl derivatives, etc.
- styryl compounds JP-A-11-242996
- triazole derivatives such as 3-(4-biphenylyl)-4-phenyl-5(4-tert-butylphenyl)-1,2,4-triazole (JP-A-11-242996) 7-41759
- phenanthroline derivatives such as bathocuproine (JP-A-10-79297)
- the compound having at least one pyridine ring substituted at the 2,4,6 positions described in International Publication No. 2005/022962 is also preferable as the material for the hole blocking layer 6 .
- the method for forming the hole blocking layer 6 is not limited, and it can be formed in the same manner as the method for forming the light emitting layer 5 described above.
- the thickness of the hole-blocking layer 6 is arbitrary as long as it does not significantly impair the effects of the present invention, but it is usually 0.3 nm or more, preferably 0.5 nm or more, and usually 100 nm or less, preferably 50 nm or less.
- the electron transport layer 7 is provided between the light emitting layer 5 or the hole element layer 6 and the electron injection layer 8 for the purpose of further improving the current efficiency of the device.
- the electron transport layer 7 is formed of a compound capable of efficiently transporting electrons injected from the cathode 9 toward the light-emitting layer 5 between electrodes to which an electric field is applied.
- the electron-transporting compound used in the electron-transporting layer 7 has a high electron injection efficiency from the cathode 9 or the electron-injecting layer 8, and has a high electron mobility and can efficiently transport the injected electrons. It must be a compound.
- electron-transporting compounds satisfying these conditions include metal complexes such as aluminum complexes of 8-hydroxyquinoline (Japanese Patent Application Laid-Open No. 59-194393) and 10-hydroxybenzo[h]quinoline.
- metal complexes such as aluminum complexes of 8-hydroxyquinoline (Japanese Patent Application Laid-Open No. 59-194393) and 10-hydroxybenzo[h]quinoline.
- metal complexes oxadiazole derivatives, distyrylbiphenyl derivatives, silole derivatives, 3-hydroxyflavone metal complexes, 5-hydroxyflavone metal complexes, benzoxazole metal complexes, benzothiazole metal complexes, trisbenzimidazolylbenzene (US Pat. No. 5,645,948 No.
- quinoxaline compound JP-A-6-207169
- phenanthroline derivative JP-A-5-331459
- 2-t-butyl-9,10-N,N'-dicyanoanthraquinone diimine 2-t-butyl-9,10-N,N'-dicyanoanthraquinone diimine
- n type hydrogenated amorphous silicon carbide n-type zinc sulfide
- n-type zinc selenide and the like.
- the film thickness of the electron transport layer 7 is usually 1 nm or more, preferably 5 nm or more, and usually 300 nm or less, preferably 100 nm or less.
- the electron-transporting layer 7 is formed on the light-emitting layer 5 or the hole-blocking layer 6 by a wet film-forming method or a vacuum deposition method in the same manner as the light-emitting layer 5 .
- a vacuum deposition method is usually used.
- the electron injection layer 8 plays a role of efficiently injecting electrons injected from the cathode 9 into the electron transport layer 7 or the light emitting layer 5 .
- the material forming the electron injection layer 8 is preferably a metal with a low work function. Examples include alkali metals such as sodium and cesium, alkaline earth metals such as barium and calcium, and the like.
- the film thickness of the electron injection layer 8 is preferably 0.1 to 5 nm.
- Inserting an extremely thin insulating film (thickness of about 0.1 to 5 nm) such as LiF, MgF 2 , Li 2 O, Cs 2 CO 3 or the like as the electron injection layer 8 at the interface between the cathode 9 and the electron transport layer 7 is also an effective method for improving the efficiency of the device (Appl. Phys. Lett., 70, 152, 1997; JP-A-10-74586; IEEE Trans. Electron. Devices, 44, 1245, 1997; SID 04 Digest, page 154).
- an organic electron-transporting material typified by a nitrogen-containing heterocyclic compound such as bathophenanthroline or a metal complex such as an aluminum complex of 8-hydroxyquinoline is doped with an alkali metal such as sodium, potassium, cesium, lithium or rubidium ( JP-A-10-270171, JP-A-2002-100478, JP-A-2002-100482, etc.), it is possible to achieve both improved electron injection and transport properties and excellent film quality.
- the film thickness is usually 5 nm or more, preferably 10 nm or more, and usually 200 nm or less, preferably 100 nm or less.
- the electron injection layer 8 is formed by laminating the light emitting layer 5, the hole blocking layer 6 thereon or the electron transporting layer 7 thereon by a wet film forming method or a vacuum vapor deposition method in the same manner as the light emitting layer 5.
- the details of the wet film formation method are the same as those of the light-emitting layer 5 described above.
- the cathode 9 plays a role of injecting electrons into a layer (the electron injection layer 8 or the light emitting layer 5 or the like) on the light emitting layer 5 side.
- the material used for the anode 2 can be used, but it is preferable to use a metal with a low work function in order to efficiently inject electrons.
- metals with a low work function for example, metals such as tin, magnesium, indium, calcium, aluminum, silver, and alloys thereof are used.
- Specific examples include low work function alloy electrodes such as magnesium-silver alloy, magnesium-indium alloy and aluminum-lithium alloy.
- the cathode 9 made of a metal with a low work function by stacking a metal layer that has a high work function and is stable against the atmosphere on the cathode 9 .
- Metals to be laminated include, for example, metals such as aluminum, silver, copper, nickel, chromium, gold, and platinum.
- the film thickness of the cathode is generally similar to that of the anode 2 .
- the electron-blocking layer prevents electrons moving from the light-emitting layer 5 from reaching the hole-transporting layer 4, thereby increasing the probability of recombination with holes in the light-emitting layer 5 and generating excitons. It has a role of confining in the light-emitting layer 5 and a role of efficiently transporting the holes injected from the hole-transporting layer 4 toward the light-emitting layer 5 .
- the electron blocking layer properties required for the electron blocking layer include high hole transportability, large energy gap (difference between HOMO and LUMO), and high excited triplet level (T1).
- the electron-blocking layer When the light-emitting layer 5 is formed by a wet film-forming method, it is preferable to form the electron-blocking layer by a wet film-forming method as well, because this facilitates the production of the device. For this reason, the electron-blocking layer also preferably has wet film-forming compatibility.
- Materials used for such an electron-blocking layer include copolymers of dioctylfluorene and triphenylamine, represented by F8-TFB (International Publication No. 2004/084260) and the like.
- the structure is reversed from that of FIG. It is also possible to laminate in the order of 2. It is also possible to provide the organic electroluminescence device of the present invention between two substrates, at least one of which is highly transparent.
- a structure structure in which a plurality of light-emitting units are stacked in which the layer structure shown in FIG. 1 is stacked in multiple stages is also possible. In that case, instead of the interface layer between the stages (between the light emitting units) (when the anode is ITO and the cathode is Al, the two layers), for example, V 2 O 5 or the like is used as the charge generation layer to form a barrier between the stages. is reduced, which is more preferable from the viewpoint of luminous efficiency and driving voltage.
- the present invention can be applied to any of a single organic electroluminescent element, an element having a structure arranged in an array, and a structure in which anodes and cathodes are arranged in an XY matrix.
- the display device and lighting device of the present invention use the organic electroluminescence device of the present invention as described above. There are no particular restrictions on the type and structure of the display device and lighting device of the present invention, and they can be assembled according to conventional methods using the organic electroluminescence device of the present invention.
- the display device and lighting device of the present invention can be produced by the method described in "Organic EL Display” (Ohmsha, August 20, 2004, by Shizuo Tokito, Chihaya Adachi, and Hideyuki Murata). can be formed.
- Example 1 A compound 1 (charge-transporting material) having a structure represented by the following formula (7) and a compound 2 (light-emitting material) having a structure represented by the following formula (8) are mixed at a mass ratio of 80:20 to emit light. It was designated as layer material 1. 2,6-Di-tert-butylphenol (BHB) equivalent to 2% by mass is added to the light-emitting layer material 1, and cyclopenta is added so that the light-emitting layer material 1 becomes 2.5% by mass with respect to the total amount of the ink. Non-methyl 2-carboxylate was added (BHB concentration 500 ppm). After the atmosphere in the container was replaced with nitrogen, the contents were dissolved by heating and stirring at 68° C. for 1 hour to prepare luminescent layer ink 1 .
- BHB 2,6-Di-tert-butylphenol
- Luminescent layer ink 2 was prepared in the same manner as in Example 1, except that dimethyl phthalate was added instead of methyl cyclopentanone-2-carboxylate.
- Luminescent layer ink 3 was prepared in the same manner as in Example 1, except that benzyl benzoate was added instead of methyl cyclopentanone-2-carboxylate.
- the surface tension was measured by the pendant drop method using a contact angle meter DM500 manufactured by Kyowa Interface Science. A droplet of ink of 3 ⁇ L was formed on the tip of the syringe, and the shape was photographed after 10 seconds. Using the analysis software FAMAS, the surface tension was calculated from this shape by the Fitting-Laplace method. For each ink, droplet formation and measurement were repeated 10 times, and the average was taken as the surface tension of the ink.
- Table 1 shows the measured values of surface tension and the amount of change in the initial surface tension and after 28 days for the light-emitting layer inks of Examples 1 and 2 and Comparative Example 1.
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Abstract
Description
インクに用いられる有機溶媒には、機能性材料を速やかに溶解することと、溶解した後、機能性材料を析出させず均一状態を保持する、という2つの意味での溶解性が求められる。
しかし、インクの液物性の安定性、とりわけ、インクの表面張力安定性の点で十分とは言えず、液物性の安定性の改善が求められていた。
dは0~4の整数である。
eは0~3の整数である。
mは1~20の整数である。
nは0~2の整数である。
環Aは、ピリジン環、ピラジン環、ピリミジン環、イミダゾール環、オキサゾール環、チアゾール環、キノリン環、イソキノリン環、キナゾリン環、キノキサリン環、アザトリフェニレン環、カルボリン環のいずれかである。
環Aは、置換基を有していても良く、該置換基は、フッ素原子、塩素原子、臭素原子、炭素数1~20のアルキル基、炭素数7~40の(ヘテロ)アラルキル基、炭素数1~20のアルコキシ基、炭素数3~20の(ヘテロ)アリールオキシ基、炭素数1~20のアルキルシリル基、炭素数6~20のアリールシリル基、炭素数2~20のアルキルカルボニル基、炭素数7~20のアリールカルボニル基、炭素数2~20のアルキルアミノ基、炭素数6~20のアリールアミノ基、及び炭素数3~20の(ヘテロ)アリール基のうちのいずれか、あるいはこれらの組み合わせである。環Aに結合する隣り合う置換基どうしが結合して環Aに縮合する環を形成しても良い。
Z1は、直接結合またはm+1価の芳香族連結基を表す。
L1は補助配位子を表す。lは1~3の整数である。補助配位子が複数ある場合は、それぞれ異なっていても良く、同一であっても良い。]
本発明の有機電界発光素子用組成物は、フェノール誘導体である前記式(1)で表される化合物を含有するため、インクを長時間保管した際も機能材料の劣化が抑制される。さらに、カルボニル基を2つ以上有する脂肪族エステル及び/又は芳香族ジエステル溶媒を溶媒として含有するため、フェノール誘導体の酸化に伴う液物性変化を小さくすることが可能である。
「ヘテロ原子を含んでいてもよい」とは、アリール基、アラルキル基またはアリールオキシ基の主骨格を形成する炭素原子のうち1または2以上の炭素原子がヘテロ原子に置換されていることを表す。
ヘテロ原子としては窒素原子、酸素原子、硫黄原子、リン原子、ケイ素原子等が挙げられる。中でも耐久性の観点から窒素原子が好ましい。
(ヘテロ)アリーレン基についても同様である。
本発明の有機電界発光素子用組成物は、機能性材料と、下記式(1)で表される化合物と、カルボニル基を2つ以上有する脂肪族エステル溶媒及び/又は芳香族ジエステル溶媒とを含むことを特徴とする。
本発明の有機電界発光素子用組成物は、機能性材料を含む。機能性材料とは、有機電界発光素子の発光層に含まれる発光材料または電荷輸送性材料である。
本発明の有機電界発光素子用組成物に含まれるイリジウム錯体は、有機溶剤への溶解性と耐熱性が高い点で、下記式(2)で表されることが好ましい。
dは0~4の整数である。
eは0~3の整数である。
mは1~20の整数である。
nは0~2の整数である。
環Aは、ピリジン環、ピラジン環、ピリミジン環、イミダゾール環、オキサゾール環、チアゾール環、キノリン環、イソキノリン環、キナゾリン環、キノキサリン環、アザトリフェニレン環、カルボリン環のいずれかである。
環Aは、置換基を有していても良く、該置換基は、フッ素原子、塩素原子、臭素原子、炭素数1~20のアルキル基、炭素数7~40の(ヘテロ)アラルキル基、炭素数1~20のアルコキシ基、炭素数3~20の(ヘテロ)アリールオキシ基、炭素数1~20のアルキルシリル基、炭素数6~20のアリールシリル基、炭素数2~20のアルキルカルボニル基、炭素数7~20のアリールカルボニル基、炭素数2~20のアルキルアミノ基、炭素数6~20のアリールアミノ基、及び炭素数3~20の(ヘテロ)アリール基のうちのいずれか、あるいはこれらの組み合わせである。環Aに結合する隣り合う置換基どうしが結合して環Aに縮合する環を形成しても良い。
Z1は、直接結合またはm+1価の芳香族連結基を表す。
L1は補助配位子を表す。lは1~3の整数である。補助配位子が複数ある場合は、それぞれ異なっていても良く、同一であっても良い。]
隣接する2つのR7が互いに連結して環を形成する場合、dは2であることが好ましい。
隣接する2つのR8が互いに連結して環を形成する場合、eは2または3であることが好ましい。
環A上の水素原子は、置換されていないことが、製造が容易な点で好ましい。
環A上の水素原子は、置換基を有しても良いフェニル基またはナフチル基で置換されていることが、有機電界発光素子に用いられたときに励起子が生成しやすくなるため、発光効率が高められる点で好ましい。
Z1は、駆動電圧が高くなる懸念が小さい点で、m+1価の芳香族連結基であることが好ましい。
下記式(2A)~(2C)中の破線は配位結合を表す。
lが1で2つの補助配位子L1が存在する場合は、補助配位子L1は互いに同一であっても良く、異なる構造であっても良い。
lが3のときは、L1は存在しない。
環Bは、耐久性の点から、ピリジン環、ピリミジン環、イミダゾール環であることが好ましく、ピリジン環であることがさらに好ましい。
環B上の水素原子は、置換されていないことが製造容易な点で好ましい。
環B上の水素原子は、置換基を有しても良いフェニル基またはナフチル基で置換されていることが、有機電界発光素子に用いられたときに励起子が生成しやすくなるため、発光効率が高められる点で好ましい。
R15~R17は置換基である。]
本発明の有機電界発光素子用組成物に、機能性材料として含まれても良い電荷輸送性材料は、正電荷(正孔)または負電荷(電子)輸送性を有する材料である。該電荷輸送性材料は、本発明の効果を損なわない限り、特に制限はなく、公知の材料を適用可能である。
Ar24、Ar25は、それぞれ独立して、置換基を有していてもよい炭素数3~30の(ヘテロ)アリール基を表す。
rは0~2の整数を表す。]
重量平均分子量が上記上限値以下であれば、溶媒に対する溶解性に優れ、成膜性にも優れる。重量平均分子量が上記下限値以上であれば、高分子化合物のガラス転移温度、融点及び気化温度が高く、耐熱性に優れる。
本発明の有機電界発光素子用組成物は、下記式(1)で表される化合物であるフェノール誘導体を含む。
すなわち、本発明の有機電界発光素子用組成物は、式(1)で表される化合物として下記式(1-1)で表される化合物を含むことが好ましい。
すなわち、本発明の有機電界発光素子用組成物は、式(1)で表される化合物として下記式(1-2)で表される化合物を含むことが好ましい。
本発明の有機電界発光素子用組成物は、カルボニル基を2つ以上有する脂肪族エステル溶媒及び/又は芳香族ジエステル溶媒を含む。
カルボニル基を2つ以上有する脂肪族エステル溶媒は、脂肪族カルボン酸エステル部分に含まれるカルボニル基の他に、もう1つ以上のカルボニル基を有する。前記溶媒がさらに有するカルボニル基は、脂肪族カルボン酸エステル基であっても、脂肪族カルボン酸エステル基でなくても良いが、脂肪族カルボン酸エステル基であることが、フェノール誘導体の酸化による構造変化によるインクの液物性の変化をさらに抑制できる点で好ましい。
芳香族ジエステル溶媒は、フェノール誘導体の酸化による構造変化によるインクの液物性の変化を効果的に抑制できる点で好ましい。芳香族ジエステル溶媒は、溶質を容易に溶解することができる点においても好ましい。
本発明の有機電界発光素子用組成物は、カルボニル基を2つ以上有する脂肪族エステル溶媒及び芳香族ジエステル溶媒以外のその他の溶媒を含んでいても良い。
融点が高く、組成物が低温に置かれた際に、凝固するおそれが小さい点で、ジアルキル化ビフェニル、トリアルキル化ビフェニルが好ましく、トリアルキル化ビフェニルがより好ましい。
適度な沸点と融点を有する点でジアルキル化ビフェニルが好ましい。
溶媒の沸点は、通常80℃以上、好ましくは100℃以上、より好ましくは150℃以上、特に好ましくは200℃以上であり、通常350℃以下、好ましくは320℃以下、より好ましくは300℃以下である。沸点がこの範囲を下回ると、湿式成膜時において、組成物からの溶媒蒸発により、成膜安定性が低下する可能性がある。
本発明の有機電界発光素子用組成物が機能性材料として発光材料を含む場合、本発明の有機電界発光素子用組成物中の発光材料の含有量(濃度)は、好ましくは0.05質量%以上、より好ましくは0.1質量%以上、さらに好ましくは0.2質量%以上で、好ましくは8.0質量%以下、より好ましくは4.0質量%以下、さらに好ましくは2.0質量%以下である。
発光材料の濃度が上記下限以上であれば十分な発光材料を含む層が形成可能である。発光材料の濃度が上記上限以下であれば溶解した発光材料を析出させずに均一な状態を保持することが容易である。
電荷輸送性材料の濃度が上記下限以上であれば十分な電荷輸送性材料を含む層が形成可能である。電荷輸送性材料の濃度が上記上限以下であれば溶解した電荷輸送性材料を析出させずに均一な状態を保持することが容易である。
機能性材料の合計の濃度が上記下限以上であれば十分な機能性材料を含む層が形成可能である。機能性材料の合計の濃度が上記上限以下であれば溶解した機能材料を析出させずに均一な状態を保持することが容易である。
フェノール誘導体の濃度が上記下限以上であればフェノール誘導体による機能性材料の劣化抑制効果を十分に得ることができる。フェノール誘導体の濃度が上記上限以下であれば発光層を成膜する際に、フェノール誘導体及びその酸化物を溶媒とともに除去することが容易である。
本発明の有機電界発光素子用組成物は、特に機能性材料として発光材料と電荷輸送性材料を含む発光層形成用組成物として好適に用いられる。
本発明の有機電界発光素子は、本発明の有機電界発光素子用組成物を用いて形成された発光層を有する。
基板1は、有機電界発光素子の支持体となるものであり、通常、石英やガラスの板、金属板や金属箔、プラスチックフィルムやシート等が用いられる。これらのうち、ガラス板や、ポリエステル、ポリメタクリレート、ポリカーボネート、ポリスルホン等の透明な合成樹脂の板が好ましい。基板1は、外気による有機電界発光素子の劣化が起こり難いことからガスバリア性の高い材質とするのが好ましい。このため、特に合成樹脂製の基板等のようにガスバリア性の低い材質を用いる場合は、基板1の少なくとも片面に緻密なシリコン酸化膜等を設けてガスバリア性を上げるのが好ましい。
陽極2は、発光層側の層に正孔を注入する機能を担う。
透明性が不要な場合は、陽極2の厚みは必要な強度等に応じて任意に厚みとすれば良く、この場合、陽極2は基板1と同一の厚みでも良い。
陽極2側から発光層5側に正孔を輸送する機能を担う層は、通常、正孔注入輸送層または正孔輸送層と呼ばれる。陽極2側から発光層5側に正孔を輸送する機能を担う層が2層以上ある場合に、より陽極2側に近い方の層を正孔注入層3と呼ぶことがある。正孔注入層3は、陽極2から発光層5側に正孔を輸送する機能を強化する点で、用いることが好ましい。正孔注入層3を用いる場合、通常、正孔注入層3は、陽極2上に形成される。
正孔注入層形成用組成物は、通常、正孔注入層3となる正孔輸送性化合物を含有する。また、湿式成膜法の場合は、通常、更に溶剤も含有する。正孔輸送性化合物は、正孔輸送性が高く、注入された正孔を効率よく輸送できるのが好ましい。このため、正孔輸送性化合物は正孔移動度が大きく、トラップとなる不純物が製造時や使用時等に発生し難いのが好ましい。また、正孔輸送性化合物は安定性に優れ、イオン化ポテンシャルが小さく、可視光に対する透明性が高いことが好ましい。特に、正孔注入層3が発光層5と接する場合は、発光層5からの発光を消光しないものや発光層5とエキサイプレックスを形成して、発光効率を低下させないものが好ましい。
正孔注入層3には、正孔輸送性化合物の酸化により、正孔注入層3の導電率を向上させることができるため、電子受容性化合物を含有していることが好ましい。
カチオンラジカル化合物としては、正孔輸送性化合物から一電子取り除いた化学種であるカチオンラジカルと、対アニオンとからなるイオン化合物が好ましい。但し、カチオンラジカルが正孔輸送性の高分子化合物由来である場合、カチオンラジカルは高分子化合物の繰り返し単位から一電子取り除いた構造となる。
ここでいう酸化重合は、モノマーを酸性溶液中で、ペルオキソ二硫酸塩等を用いて化学的に、または、電気化学的に酸化するものである。この酸化重合(脱水素重合)の場合、モノマーが酸化されることにより高分子化されるとともに、酸性溶液由来のアニオンを対アニオンとする、高分子の繰り返し単位から一電子取り除かれたカチオンラジカルが生成する。
湿式成膜法により正孔注入層3を形成する場合、通常、正孔注入層3となる材料を可溶な溶剤(正孔注入層用溶剤)と混合して成膜用の組成物(正孔注入層形成用組成物)を調製し、この正孔注入層形成用組成物を正孔注入層3の下層に該当する層(通常は、陽極2)上に湿式成膜法により成膜し、乾燥させることにより形成させる。成膜した膜の乾燥は、後述の湿式成膜法による発光層5の形成における乾燥方法と同様に行うことができる。
芳香族炭化水素系溶剤としては、例えば、トルエン、キシレン、シクロヘキシルベンゼン、3-イソプロピルビフェニル、1,2,3,4-テトラメチルベンゼン、1,4-ジイソプロピルベンゼン、メチルナフタレン等が挙げられる。
これらの他、ジメチルスルホキシド等も用いることができる。
真空蒸着法により正孔注入層3を形成する場合には、通常、正孔注入層3の構成材料(前述の正孔輸送性化合物、電子受容性化合物等)の1種類または2種類以上を真空容器内に設置された坩堝に入れ(2種類以上の材料を用いる場合は、通常各々を別々の坩堝に入れ)、真空容器内を真空ポンプで10-4Pa程度まで排気した後、坩堝を加熱して(2種類以上の材料を用いる場合は、通常各々の坩堝を加熱して)、坩堝内の材料の蒸発量を制御しながら蒸発させ(2種類以上の材料を用いる場合は、通常各々独立に蒸発量を制御しながら蒸発させ)、坩堝に向き合って置かれた基板上の陽極2上に正孔注入層3を形成させる。2種類以上の材料を用いる場合は、それらの混合物を坩堝に入れ、加熱、蒸発させて正孔注入層3を形成することもできる。
正孔輸送層4は、陽極2側から発光層5側に正孔を輸送する機能を担う層である。正孔輸送層4は、本発明の有機電界発光素子では、必須の層では無いが、陽極2から発光層5に正孔を輸送する機能を強化する点では、この層を設けることが好ましい。正孔輸送層4を設ける場合、通常、正孔輸送層4は、陽極2と発光層5の間に形成される。上述の正孔注入層3がある場合、正孔輸送層4は正孔注入層3と発光層5の間に形成される。
湿式成膜法で正孔輸送層4を形成する場合は、通常、上述の正孔注入層3を湿式成膜法で形成する場合と同様にして、正孔注入層形成用組成物の代わりに正孔輸送層形成用組成物を用いて形成させる。
正孔輸送層形成用組成物中における正孔輸送性化合物の濃度は、正孔注入層形成用組成物中における正孔輸送性化合物の濃度と同様の範囲とすることができる。
真空蒸着法で正孔輸送層4を形成する場合についても、通常、上述の正孔注入層3を真空蒸着法で形成する場合と同様にして、正孔注入層3の構成材料の代わりに正孔輸送層4の構成材料を用いて形成させることができる。蒸着時の真空度、蒸着速度及び温度などの成膜条件などは、前記正孔注入層3の真空蒸着時と同様の条件で成膜することができる。
発光層5は、一対の電極間に電界が与えられた時に、陽極2から注入される正孔と陰極9から注入される電子が再結合することにより励起され、発光する機能を担う層である。発光層5は、陽極2と陰極9の間に形成される層であり、発光層5は、陽極2の上に正孔注入層3がある場合は、正孔注入層3と陰極9の間に形成され、陽極2の上に正孔輸送層4がある場合は、正孔輸送層4と陰極9との間に形成される。
また、発光材料としては、イリジウムを中心元素とする有機金属錯体であるイリジウム錯体が好ましいが、適宜他の発光材料を用いても良い。
以下、イリジウム錯体化合物以外の他の発光材料について詳述する。
発光材料は、所望の発光波長で発光し、本発明の効果を損なわない限り特に制限はなく、公知の発光材料を適用可能である。発光材料は、蛍光発光材料でも、燐光発光材料でもよいが、発光効率が良好である材料が好ましく、内部量子効率の観点から燐光発光材料が好ましい。
青色発光を与える蛍光発光材料(青色蛍光発光材料)としては、例えば、ナフタレン、ペリレン、ピレン、アントラセン、クマリン、クリセン、p-ビス(2-フェニルエテニル)ベンゼン及びそれらの誘導体等が挙げられる。
緑色発光を与える蛍光発光材料(緑色蛍光発光材料)としては、例えば、キナクリドン誘導体、クマリン誘導体、Al(C9H6NO)3などのアルミニウム錯体等が挙げられる。
黄色発光を与える蛍光発光材料(黄色蛍光発光材料)としては、例えば、ルブレン、ペリミドン誘導体等が挙げられる。
赤色発光を与える蛍光発光材料(赤色蛍光発光材料)としては、例えば、DCM(4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran)系化合物、ベンゾピラン誘導体、ローダミン誘導体、ベンゾチオキサンテン誘導体、アザベンゾチオキサンテン等が挙げられる。
電荷輸送性材料は、正電荷(正孔)または負電荷(電子)輸送性を有する材料であり、本発明の効果を損なわない限り、特に制限はなく、公知の材料を適用可能である。
電荷輸送性材料は、従来、有機電界発光素子の発光層5に用いられている化合物等を用いることができ、特に、発光層5のホスト材料として使用されている化合物が好ましい。
発光層5の形成方法は、真空蒸着法でも、湿式成膜法でもよいが、成膜性に優れることから、湿式成膜法が好ましい。
本発明においては、この発光層形成用組成物として、前述の本発明の有機電界発光素子用組成物を用いることが好ましい。
発光層5と後述の電子注入層8との間に、正孔阻止層6を設けても良い。正孔阻止層6は、発光層5の上に、発光層5の陰極9側の界面に接するように積層される層である。
正孔阻止層6の膜厚は、本発明の効果を著しく損なわない限り任意であるが、通常0.3nm以上、好ましくは0.5nm以上であり、通常100nm以下、好ましくは50nm以下である。
電子輸送層7は素子の電流効率をさらに向上させることを目的として、発光層5または正孔素子層6と電子注入層8との間に設けられる。
電子輸送層7は、電界を与えられた電極間において陰極9から注入された電子を効率よく発光層5の方向に輸送することができる化合物により形成される。電子輸送層7に用いられる電子輸送性化合物としては、陰極9または電子注入層8からの電子注入効率が高く、かつ、高い電子移動度を有し注入された電子を効率よく輸送することができる化合物であることが必要である。
電子輸送層7は、発光層5と同様にして湿式成膜法、或いは真空蒸着法により発光層5または正孔阻止層6上に積層することにより形成される。通常は、真空蒸着法が用いられる。
電子注入層8は、陰極9から注入された電子を効率良く、電子輸送層7または発光層5へ注入する役割を果たす。
電子注入を効率よく行うには、電子注入層8を形成する材料は、仕事関数の低い金属が好ましい。例としては、ナトリウムやセシウム等のアルカリ金属、バリウムやカルシウムなどのアルカリ土類金属等が用いられる。
電子注入層8の膜厚は、0.1~5nmが好ましい。
さらに、バソフェナントロリン等の含窒素複素環化合物や8-ヒドロキシキノリンのアルミニウム錯体などの金属錯体に代表される有機電子輸送材料に、ナトリウム、カリウム、セシウム、リチウム、ルビジウム等のアルカリ金属をドープする(特開平10-270171号公報、特開2002-100478号公報、特開2002-100482号公報などに記載)ことにより、電子注入・輸送性が向上し優れた膜質を両立させることが可能となるため好ましい。この場合の膜厚は通常5nm以上、好ましくは10nm以上で、通常200nm以下、好ましくは100nm以下である。
湿式成膜法の場合の詳細は、前述の発光層5の場合と同様である。
陰極9は、発光層5側の層(電子注入層8または発光層5など)に電子を注入する役割を果たす。陰極9の材料としては、前記の陽極2に使用される材料を用いることが可能であるが、効率よく電子注入を行なう上では、仕事関数の低い金属を用いることが好ましい。仕事関数の低い金属としては、例えば、スズ、マグネシウム、インジウム、カルシウム、アルミニウム、銀等の金属またはそれらの合金などが用いられる。具体例としては、例えば、マグネシウム-銀合金、マグネシウム-インジウム合金、アルミニウム-リチウム合金等の低仕事関数の合金電極などが挙げられる。
陰極の膜厚は通常、陽極2と同様である。
以上、図1に示す層構成の素子を中心に説明してきたが、本発明の有機電界発光素子における陽極2及び陰極9と発光層5との間には、その性能を損なわない限り、上記説明にある層の他にも、任意の層を有していても良い。また発光層5以外の任意の層を省略しても良い。
発光層5を湿式成膜法で形成する場合、電子阻止層も湿式成膜法で形成することが、素子製造が容易となるため、好ましい。
このため、電子阻止層も湿式成膜適合性を有することが好ましく、このような電子阻止層に用いられる材料としては、F8-TFBに代表されるジオクチルフルオレンとトリフェニルアミンの共重合体(国際公開第2004/084260号)等が挙げられる。
図1に示す層構成を複数段重ねた構造(発光ユニットを複数積層させた構造)とすることも可能である。その際には段間(発光ユニット間)の界面層(陽極がITO、陰極がAlの場合はその2層)の代わりに、例えばV2O5等を電荷発生層として用いると段間の障壁が少なくなり、発光効率・駆動電圧の観点からより好ましい。
本発明の表示装置及び照明装置は、上述のような本発明の有機電界発光素子を用いたものである。本発明の表示装置及び照明装置の形式や構造については特に制限はなく、本発明の有機電界発光素子を用いて常法に従って組み立てることができる。
[実施例1]
下記式(7)で示される構造を有する化合物1(電荷輸送性材料)と、下記式(8)で示される構造を有する化合物2(発光材料)を80:20の質量比で混ぜ合わせ、発光層材料1とした。発光層材料1に対し、2質量%相当の2,6-ジ-tert-ブチルフェノール(BHB)を添加し、さらに、発光層材料1がインク全量に対し2.5質量%になるようにシクロペンタノン-2-カルボン酸メチルを添加した(BHB濃度500ppm)。
容器内雰囲気を窒素に置換した後に68℃で1時間加熱攪拌して溶解させ、発光層インク1を作製した。
シクロペンタノン-2-カルボン酸メチルに替えてフタル酸ジメチルを添加したこと以外は実施例1と同様にして発光層インク2を作製した。
シクロペンタノン-2-カルボン酸メチルに替えて安息香酸ベンジルを添加したこと以外は実施例1と同様にして発光層インク3を作製した。
表面張力は、共和界面科学製 接触角計DM500を用い、ペンダントドロップ法により測定した。
3μLのインクの液滴をシリンジ先端に形成し、10秒後の形状を撮影した。解析ソフトFAMASを用い、この形状からFitting-Laplace法により表面張力を算出した。
各インクについて、それぞれ10回液滴の作成と測定を繰り返し、平均をインクの表面張力とした。
各発光層インク作製後、窒素封入されたインク容器のバイアルを室温に冷却した。このバイアルを大気開放し、直ちに半量のインクを採取し、初回の表面張力測定を行った(初期表面張力)。残りの半量インクを、大気雰囲気で再度封じ、常温環境で28日間保管した。その後、保管したインクで2回目の表面張力測定を行った(28日後表面張力)。
実施例1、2及び比較例1の発光層インクについて、初期及び28日後の表面張力の測定値とその変化量を表1に示す
本出願は、2021年5月6日付で出願された日本特許出願2021-078651及び2021年5月6日付で出願された日本特許出願2021-078652に基づいており、その全体が引用により援用される。
2 陽極
3 正孔注入層
4 正孔輸送層
5 発光層
6 正孔阻止層
7 電子輸送層
8 電子注入層
9 陰極
10 有機電界発光素子
Claims (14)
- 前記カルボニル基を2つ以上有する脂肪族エステル溶媒が、エステル基を2つ有する化合物である請求項1に記載の有機電界発光素子用組成物。
- 前記カルボニル基を2つ以上有する脂肪族エステル溶媒が、エステル基を1つ、ケトン基を1つ有する化合物である請求項1に記載の有機電界発光素子用組成物。
- 前記機能性材料として、イリジウム錯体を含む請求項1~7のいずれか1項に記載の有機電界発光素子用組成物。
- 前記機能性材料として、下記式(2)で表されるイリジウム錯体を含む請求項8に記載の有機電界発光素子用組成物。
dは0~4の整数である。
eは0~3の整数である。
mは1~20の整数である。
nは0~2の整数である。
環Aは、ピリジン環、ピラジン環、ピリミジン環、イミダゾール環、オキサゾール環、チアゾール環、キノリン環、イソキノリン環、キナゾリン環、キノキサリン環、アザトリフェニレン環、カルボリン環のいずれかである。
環Aは、置換基を有していても良く、該置換基は、フッ素原子、塩素原子、臭素原子、炭素数1~20のアルキル基、炭素数7~40の(ヘテロ)アラルキル基、炭素数1~20のアルコキシ基、炭素数3~20の(ヘテロ)アリールオキシ基、炭素数1~20のアルキルシリル基、炭素数6~20のアリールシリル基、炭素数2~20のアルキルカルボニル基、炭素数7~20のアリールカルボニル基、炭素数2~20のアルキルアミノ基、炭素数6~20のアリールアミノ基、及び炭素数3~20の(ヘテロ)アリール基のうちのいずれか、あるいはこれらの組み合わせである。環Aに結合する隣り合う置換基どうしが結合して環Aに縮合する環を形成しても良い。
Z1は、直接結合またはm+1価の芳香族連結基を表す。
L1は補助配位子を表す。lは1~3の整数である。補助配位子が複数ある場合は、それぞれ異なっていても良く、同一であっても良い。] - 請求項1~10のいずれか1項に記載の有機電界発光素子用組成物を用いて湿式成膜法にて発光層を形成する工程を含む有機電界発光素子の製造方法。
- 請求項1~10のいずれか1項に記載の有機電界発光素子用組成物を用いて形成された発光層を有する有機電界発光素子。
- 請求項12に記載の有機電界発光素子を有する表示装置。
- 請求項12に記載の有機電界発光素子を有する照明装置。
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