WO2004095891A1 - 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、照明装置、表示装置 - Google Patents
有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、照明装置、表示装置 Download PDFInfo
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- WO2004095891A1 WO2004095891A1 PCT/JP2004/005621 JP2004005621W WO2004095891A1 WO 2004095891 A1 WO2004095891 A1 WO 2004095891A1 JP 2004005621 W JP2004005621 W JP 2004005621W WO 2004095891 A1 WO2004095891 A1 WO 2004095891A1
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- FILUFGAZMJGNEN-UHFFFAOYSA-N pent-1-en-3-yne Chemical group CC#CC=C FILUFGAZMJGNEN-UHFFFAOYSA-N 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000004675 pentylcarbonyl group Chemical group C(CCCC)C(=O)* 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000006410 propenylene group Chemical group 0.000 description 1
- 125000004673 propylcarbonyl group Chemical group 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229940070891 pyridium Drugs 0.000 description 1
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- DLJHXMRDIWMMGO-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1.C1=CN=C2C(O)=CC=CC2=C1 DLJHXMRDIWMMGO-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000001360 synchronised effect Effects 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical group S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
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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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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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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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- H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
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- H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
- H10K85/146—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE poly N-vinylcarbazol; Derivatives thereof
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- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
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- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
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- H10K85/348—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising osmium
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- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Definitions
- the present invention relates to a material for an organic electroluminescent device, an organic electroluminescent device, a lighting device, and a display device.
- an electroluminescent display As a light-emitting electronic display device.
- the components of the ELD include an inorganic EL device and an organic EL device (hereinafter also referred to as an organic EL device).
- Inorganic electroluminescent elements have been used as flat light sources, but high voltage AC is required to drive the light emitting elements.
- an organic EL device has a configuration in which a light-emitting layer containing a compound that emits light is sandwiched between a cathode and an anode, and electrons and holes are injected into the light-emitting layer and recombined to form excitons.
- Exciton a light-emitting layer containing a compound that emits light is sandwiched between a cathode and an anode, and electrons and holes are injected into the light-emitting layer and recombined to form excitons.
- Exciton and emits light by using light emission (fluorescence and phosphorescence) when the exciton is deactivated. It can emit light at a voltage of several volts to several tens of volts. Because of the self-luminous type, it has a wide viewing angle, high visibility, and because it is a thin-film type solid-state device, attention is paid to space saving and portability. —
- a device having an organic light-emitting layer in which a hydroxyquinoline aluminum complex is used as a host compound and a small amount of phosphor is added thereto for example, see Patent Document 2
- an 8-hydroxyquinoline aluminum complex is used as a host compound
- a device having an organic light emitting layer doped with a quinacridone dye has been known (for example, see Patent Document 3).
- the generation ratio of a singlet exciton to a triplet exciton is 1: 3; Since it is 5% and the light extraction efficiency is about 20%, the limit of the external extraction quantum efficiency (?? eXt) is set to 5%.
- Non-Patent Document 1 Since Princeton University reported an organic EL device using phosphorescence emission from an excited triplet (for example, see Non-Patent Document 1), research on materials exhibiting phosphorescence at room temperature has been active. (See, for example, Non-Patent Document 2 and Patent Document 4.)
- the upper limit of the internal quantum efficiency is 100%, so the luminous efficiency is quadrupled in principle compared to the case of the excited singlet, and performance almost equivalent to that of a cold cathode tube can be obtained. It can also be used for lighting and is attracting attention.
- Non-Patent Document 3 many compounds have been studied for synthesis centered on heavy metal complexes such as iridium complexes (for example, see Non-Patent Document 3).
- Tris (2-phenylpyridine) iridium is used as a dopant.
- Non-Patent Document 2 for example, see Non-Patent Document 2.
- L 2 Ir (acac) ⁇ such as (ppy) 2 Ir (acac) (see, for example, Non-Patent Document 4) is used as a dopant
- Tris (2- (p-tolyl) is used as a dopant.
- pyridine Lee Rijiumu (I r (ptpy) 3) ⁇ preparative squirrel (base down zone [h] quinoline Li down)
- Lee Rijiumu (I r (bzq) 3) , I r (bzq) 2 C 1 P (B u Investigations using 3 etc. (for example, see Non-Patent Document 5) have been conducted.
- a compound having a hole transporting property is used as a host of a phosphorescent compound (for example, see Non-Patent Document 6).
- Non-Patent Document 4 various electron-transporting materials are used as hosts for phosphorescent compounds by doping them with a novel iridium complex (for example, see Non-Patent Document 4). Furthermore, high luminous efficiency is obtained by introducing a hole block layer (for example, see Non-Patent Document 5).
- the present invention has been made in view of the above problems, and an object of the present invention is to provide a material for an organic EL device having high luminous efficiency, an organic EL device using the material for an organic EL device, It is to provide a lighting device and a display device. Further, it is intended to provide a material for an organic EL device having a long life, an organic EL device using the material for an organic EL device, a lighting device, a display device, and a novel compound suitably used as the material for the organic EL device. It is.
- organic EL element materials such as a host material in an organic EL element using phosphorescence
- materials including a nitrogen-containing aromatic ring compound such as a CBA or the like are high in CBP and other organic EL element materials.
- the present inventors have found that certain nitrogen-containing aromatic ring compounds, including some carbazolic green bodies, are highly efficient as materials for organic EL devices. Was found.
- Patent Document 5 does not disclose a nitrogen-containing aromatic ring compound having a diazaforce rubazole structure.
- Patent Document 6 discloses that a nitrogen-containing aromatic ring compound having a molecular weight of 45 Only less than 0 are disclosed. In addition, there is no disclosure of a phosphorescent organic electroluminescent device.
- Patent Document 3 Patent Document 3
- Patent Document 4 Patent Document 4
- Patent Document 5 (Patent Document 5)
- Patent Document 6 (Patent Document 6)
- Non-Patent Document 3 (Non-Patent Document 3)
- Non-patent document 4 (Non-patent document 4)
- Non-Patent Document 5 (Non-Patent Document 5)
- Non-Patent Document 6 (Non-Patent Document 6)
- a material for an organic electroluminescent device which is represented by the following general formula (1) and is a pyrrole derivative having a molecular weight of 45 ° or more.
- Z 2 represents an atomic group necessary for forming a nitrogen-containing heterocyclic ring each 5-membered to 7-membered.
- Ar represents an aryl group which may have a substituent or a heterocyclic group which may have a substituent
- R 3 represents a hydrogen atom or a substituent
- Z 3 , Z 4 represents an atom group necessary to form a 5- to 7-membered ring structure.
- the pyrrol derivative represented by the general formula (1) is any one of pyrrole derivatives represented by the following general formulas (3) to (6). 4.
- R 4 , R 7 , R 13 represents an alkyl group which may have a substituent, a cycloalkyl group which may have a substituent, an aryl group which may have a substituent or a substituent.
- R 5, R 6, R 8 , R 9, Rii, R 12, R 14, R 15 each represent a substituent.
- Z 5 to Z 8 each represent an atom group necessary to form a 5- to 7-membered ring structure.
- n1 represents an integer of 0 to 3
- n2 and n3 represent integers of 0 to 2.
- the pyrrole derivative represented by the general formula (1) is any one of pyrrole derivatives represented by the following general formulas (7) to (10). Materials for organic electroluminescence devices.
- R 16 , R 19 , R 32 , and R 25 each represent an alkyl group optionally having a substituent, a cycloalkyl group optionally having a substituent, Represents an aryl group or a heterocyclic group which may have a substituent R 17 , R 18 , R 2 ⁇ R 21 , R 23 , R 24 , R 26 and R 27 each represent a substituent N 4 represents an integer of 0 to 4, and n 5 to 11 1 represents an integer of 0 to 3.
- R 28, R 29 each represent a hydrogen atom or a substituent
- Z 9 represents an atomic group necessary to form a 5- to 7-membered ring structure
- Z 10 Has 5 members each Represents a group of atoms necessary to form a 7-membered nitrogen-containing heterocyclic ring
- L represents a divalent to tetravalent linking group
- m and n each represent an integer of 1-2.
- the pyrrole derivative represented by the general formula (1) or (2) has a maximum fluorescence emission wavelength of 500 nm or less. 12.
- An organic electroluminescent device according to any one of (1) to (6), further comprising a constituent layer including at least a light-emitting layer between the pair of electrodes.
- An organic electroluminescence device comprising a material for use.
- a lighting device comprising the organic electroluminescent element according to any one of (7) to (; L1).
- a display device comprising the organic electroluminescent element according to any one of (7) to (; L1).
- FIG. 1 is a schematic diagram illustrating an example of a display device including an organic EL element.
- FIG. 2 is a schematic diagram of a display unit.
- FIG. 3 is a schematic diagram of a pixel.
- FIG. 4 is a schematic diagram of a passive matrix type full color display device. BEST MODE FOR CARRYING OUT THE INVENTION
- an organic EL element In the organic electroluminescent element (hereinafter, referred to as an organic EL element) of the present invention, by using at least one kind of material for an organic EL element defined in any one of the above items 1 to 6, An organic EL device exhibiting high luminance, high external extraction efficiency, and a long driving life, as defined in any one of 11 above, was obtained. Further, a display device and a lighting device including the organic EL element of the present invention could be provided together.
- the material for an organic EL device represented by the general formula (1) according to the present invention will be described. As a result of intensive studies, the present inventors have found that an organic EL device using the material for an organic EL device represented by the general formula (1) has high luminous efficiency. Furthermore, they have found that an organic EL device using the material for an organic EL device represented by the general formula (1) exhibits high external extraction efficiency and a long driving life.
- a pyrrole derivative represented by the general formula (2) and any one of the pyrrole represented by the general formulas (3) to (6) are described below.
- the derivative, any one of the pyrrole derivatives represented by the general formulas (7) to (10), or the pyrrole derivative represented by the general formula (11) is an effect according to the present invention. Was found to be more preferable.
- examples of the alkyl group which may have a substituent represented by are, for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a pentyl group, Examples include a hexyl group, an octyl group, a dodecyl group, a tridecyl group, a tetradecyl group, and a pentadecyl group. Examples of the substituent which may have, and the like substituents represented by later-described R 2.
- examples of the optionally substituted cycloalkyl group represented by Ri include a cyclopentyl group and a cyclohexyl group.
- examples of the substituent which may be possessed include a substituent represented by R 2 described below.
- examples of the aryl group which may have a substituent represented by: phenyl, p-chlorophenyl, menthyl, tolyl, xylyl, Examples include a biphenylyl group, a naphthyl group, an anthryl group, and a phenanthryl group.
- examples of the substituent that may be present include a substituent represented by R 2 described below.
- examples of the optionally substituted heterocyclic group represented by the formula include a furyl group, a phenyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, and a triazinyl group.
- the diaza-power basazolyl group is a group in which at least one of the carbon atoms constituting the power-type porporin ring is substituted with a nitrogen atom, and may be abbreviated as an azacarbolinyl group), a quinazolinyl group, Aromatic heterocyclic groups such as phthalazinyl group, isochromanyl group, pyrrolidinyl group, chromanyl group, imidazolidinyl group, imidazolinyl group, morpholinyl group, piperidyl group, piperazinyl group, pyrazolinyl group, pyrazolidinyl group, And a non-aromatic heterocyclic group such as an oxazolidinyl group.
- substituent that may be
- the substituent represented by R 2 is an alkyl group (for example, a methyl group, an ethyl group, a propyl group, an isopropyl group, a tert-butyl group, a pentyl group, a hexyl group, an octyl group) Group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, etc.), cycloalkyl group (eg, cyclopentyl group, cyclohexyl group, etc.), alkenyl group (eg, vinyl group, aryl group, etc.), alkynyl group (eg, For example, an ethynyl group, a propargyl group, etc.), an aryl group (eg, a phenyl group, a naphthyl group, etc.), an aromatic heterocyclic group (eg, a furyl group
- alkoxycarbonyl group eg, a methyloxycarbonyl group, an ethyloxycarbonyl group, a butyloxycarbonyl group, an octyloxycarbonyl group, a dodecyloxycarbonyl group, etc.
- an aryloxycarbonyl group Group for example, phenyloxycarbonyl group, Tyloxycarbonyl group, etc.
- sulfamoyl group for example, aminosulfonyl group, methylaminosulfonyl group, dimethylaminosulfonyl group, butylaminosulfonyl group, hexylaminosulfonyl group, cyclohexylaminosulfonyl group, octyla
- Minosulfonyl group dodecylaminosulfonyl group, phenylaminosulfonyl group, naphthylaminosulfonyl group, 2-pyr
- substituents may be further substituted by the above-mentioned substituents. Further, a plurality of these substituents may be bonded to each other to form a ring.
- the 5- to 7-membered ring structure formed by is a cyclopentene ring, a cyclopentadiene ring, a benzene ring, a pyridine ring, a thiopyran ring, a virane ring, a cyclohexene ring, Hexadiene ring, cycloheptene ring, cycloheptadiene ring, furan ring, thiophene ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, triazine ring, oxaziazole ring, triazolyl ring, imidazole Ring, pyrazole ring, thiazole ring, indole ring and the like.
- the 5- to 7-membered ring structure formed by Z i may have a substituent represented by R 2 in the general formula (1).
- examples of the 5- to 7-membered nitrogen-containing heterocyclic structure formed by Z 2 include a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, and an oxaziazole. Ring, triazolyl ring, imidazole ring, pyrazolyl ring, thiazole ring and the like. Further, the 5- to 7-membered ring structure formed by the above may have a substituent represented by R 2 in the general formula (1). Further, the 5- to 7-membered ring structure formed by the above may have a substituent represented by R 2 in the above general formula (1).
- the organic EL device material represented by the general formula (2) according to the present invention will be described.
- the aryl group which may have a substituent represented by A r has a substituent represented by the following formula in the general formula (1). Is synonymous with the good aryl group.
- the optionally substituted heterocyclic group represented by A ri may have a substituent represented by R i in the general formula (1). This is synonymous with a heterocyclic group.
- the 5- to 7-membered ring structure represented by Z 3 has the same meaning as the 5- to 7-membered ring structure formed by in the general formula (1).
- the 5- to 7-membered nitrogen-containing heterocyclic structure formed by Z 4 is a 5- to 7-membered nitrogen-containing heterocyclic structure formed by Z 2 in the general formula (1). It has the same meaning as the nitrogen-containing heterocyclic structure.
- R 4 , R 7 and R io R 13 each may have a substituent, and may have a substituent.
- the cycloalkyl group, the aryl group which may have a substituent, and the heterocyclic group which may have a substituent have the substituent represented by the formula in the general formula (1).
- a cycloalkyl group which may have a substituent, an aryl group which may have a substituent, and a heterocyclic group which may have a substituent JP2004 / 005621
- the 5- to 7-membered ring structure represented by Z 5 to Z S is a 5- to 7-membered ring structure formed by the general formula (1). Synonymous.
- R 16 , R 19 , R 22 , and R 25 each represent an alkyl group which may have a substituent or a substituent which may have a substituent.
- the good cycloalkyl group, the aryl group which may have a substituent, and the heterocyclic group which may have a substituent have the substituent represented by the formula in the general formula (1).
- the 5- to 7-membered ring structure formed by Z 9 and Z 12 is a 5- to 7-membered ring structure formed by the following formula in the general formula (1): Is synonymous with
- the 5- to 7-membered nitrogen-containing heterocyclic ring formed by Z 10 is a 5- to 7-membered nitrogen-containing heterocyclic ring formed by Z 2 in the general formula (1). It has the same meaning as the nitrogen-containing heterocyclic structure.
- examples of the divalent linking group represented by L include a hydrocarbon group such as an alkylene group, an alkenylene group, an alkynylene group, and an arylene group;
- the alkenylene group, the alkynylene group, and the arylene group may each contain a hetero atom (for example, a nitrogen atom, a sulfur atom, a silicon atom, and the like), and may be a thiophene-2,5-diyl group or a pyrazine.
- It may be a divalent linking group derived from a compound having an aromatic heterocycle (also referred to as a heteroaromatic compound), such as a 1,2,3-diyl group, or a chalcogen atom such as oxygen or sulfur. You may. Further, a group connecting and linking hetero atoms, such as an alkylimino group, a dialkylsilandiyl group and a diarylgermandyl group, may be used.
- alkylene group used as the divalent linking group represented by L examples include an ethylene group, a trimethylene group, a tetramethylene group, a propylene group, an ethylethylene group, a pentamethylene group, a hexamethylene group, and 2,2. , 41 Trimethylhexamethylene group, heptamethylene group, octamethylene group, nonamethylene group, decamethylene group, pendecamethylene group, dodecamethylene group, cyclohexylene P2004 / 005621
- the alkenylene group used as the divalent linking group represented by L includes, for example, a propenylene group, a vinylene group (also referred to as an ethenylene group), a 4-propyl-l-pentenylene group And the like.
- alkynylene group used as the divalent linking group represented by L examples include an ethynylene group, a 3-pentynylene group, and the like.
- Examples of the arylene group used as the divalent linking group represented by L include 0-phenylene group, m-phenylene group, p-phenylene group, naphthalenediyl group, anthracenediyl group, naphthacenedyl group, Pyrylene diyl group, naphthyl naphthalene diyl group, biphenyl diyl group (for example, 3,3'-biphenyl diyl group, 3,6-biphenyl diyl group, etc.), terphenyl diyl group, quaterphenyl diyl group, kink phenyl
- Examples of the group include a nildiyl group, a sexpenyldiyl group, a septiphenyldiyl group, an octiphenylyl group, a nobiphenyldiyl group, and a diphenyldiyl group.
- Examples of the group having a divalent heterocyclic group used as the divalent linking group represented by L include, for example, an oxazodyldiyl group, a pyrimidinediyl group, a pyridazinediyl group, a vilandiyl group, a pyrrolidinyl group, and Midazolidinyl group, imidazolidinyl group, pyrazolidinediyl group, pyrazolidinyl group, pyridindiyl group, piperazinediyl group, morpholindyl group, quinuclidinediyl group, and the like.
- a compound having an aromatic heterocycle also referred to as a heteroaromatic compound
- L as the trivalent linking group represented by L, for example, an ethanetriyl group, a propanetriyl group, a pentanetriyl group, a pentanetriyl group, a hexanetriyl group, a heptantryyl group, an octantryyl group , Nonantriyl, decantryyl, undecantryyl, dodecanetriyl, cyclohexanetriyl, cyclopentanetriyl, benzenetriyl, naphthalenetriyl, triazinetriyl, and the like.
- examples of the tetravalent linking group represented by L include a propanediylidene group, a 1,3-propanediyl2_ylidene group, a butanedilidene group, a pentanedylidene group, Hexanedilidene group, heptanedilidene group, octanediylidene group, nonanediylidene group, decanedilidene group, pendecandilidene group, dodecanedilidene group, cyclohexanedilidene group, cyclopentanedylidene group, benzenetetrayl group, naphthalenetetrayl And the above-mentioned trivalent group represented by L with one more bonding group (which becomes tetravalent when the divalent bonding group is substituted), and the like. It can be used as a linking group
- Exemplified Compound 7 was confirmed by 1 H-NMR spectrum and mass spectrometry.
- the physical property data and spectrum data of Exemplified Compound 7 are shown below.
- Exemplified Compound 18 was confirmed by 1 H-NMR spectrum and mass spectrometry.
- the spectrum data of the exemplified compound 18 are as follows.
- the material for an organic EL device of the present invention has a molecular weight of 450 or more, but the molecular weight is preferably 600 or more, and more preferably 800 or more. As a result, the glass transition temperature is increased, the thermal stability is improved, and the life can be further extended.
- the mass spectrometer is commercially available.
- the molecular weight is measured.
- the molecular weight of the pyrrole derivative is 1000 or more, the molecular weight is measured using GPC (gel permeation chromatography) using THF (tetrahydrofuran) as a column solvent.
- the GPC measurement conditions are as follows: stabilize the column at 0 ° C, flow THF at a flow rate of 1 ml per minute, and inject about 100 1 of a sample with a concentration of 1 mg gZm1 for measurement.
- the column it is preferable to use a combination of a commercially available polystyrene column.
- a refractive index detector IR detector
- a UV detector is preferably used.
- the molecular weight distribution of the sample is calculated using a calibration curve created using monodispersed polystyrene standard particles. It is preferable to use about 10 points as polystyrene for preparing a calibration curve.
- Calibration curves were prepared using at least eight types of polyoxyethylene daricol (manufactured by Tosoh Corporation; TSKS TANDARD P OLYETHYLENE OX IDE) having different molecular weights.
- the material for an organic EL device of the present invention is used as a constituent component of a constituent layer of an organic EL device described later, and is contained in a light emitting layer or a hole blocking layer in the constituent layers of the organic EL device of the present invention. It is preferably a light emitting layer, and particularly preferably used as a host compound of the light emitting layer.
- the material for an organic EL device of the present invention or the compound of the present invention may be used in other constituent layers of an organic EL device as necessary from the viewpoint of controlling various physical properties of the organic EL device.
- the compound of the present invention is a material for an organic EL device (backlight, flat panel display, illumination light source, display device, light source for electrophotography, recording light source, exposure light source, reading light source, sign, sign, interior, optical communication device, etc.)
- organic semiconductor laser materials recording light source, exposure light source, reading light source optical communication device, electrophotographic light source, etc.
- electrophotographic photoreceptor materials It can be used in a wide range of fields, such as materials for organic TFT devices (organic memory devices, organic computing devices, organic switching devices), materials for organic wavelength conversion devices, and materials for photoelectric conversion devices (solar cells, optical sensors, etc.). is there.
- a metal, an alloy, an electrically conductive compound, or a mixture thereof having a large work function (4 eV or more) as an electrode material is preferably used.
- Metals such as A u Specific examples of such an electrode material, C ul, I Nji ⁇ mucin O dimethylsulfoxide (I TO), like S n 0 2, Z n conductive transparent material such as O is. Further, a material such as IDI XO (InaOa-Z ⁇ ) which is capable of forming an amorphous and transparent conductive film may be used.
- the anode may be formed into a thin film by a method such as evaporation or sputtering of these electrode substances, and a pattern of a desired shape may be formed by a photolithography method, or a pattern accuracy is required. If not (approximately 100 or more), a pattern may be formed through a mask having a desired shape during the deposition and sputtering of the electrode material.
- the transmittance is desirably greater than 10%
- the sheet resistance of the anode is preferably several hundred ⁇ / b or less.
- the film thickness depends on the material, but is usually selected in the range of 10 nm to 1,000 nm, preferably 10 nm to 200 nm. —
- the cathode a metal having a low work function (4 eV or less) (electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof are used as the electrode material.
- the electrode substance include sodium, sodium Umukariumu alloy, magnesium, lithium, magnesium / copper mixtures, Ma Guneshiumu z silver mixture, a magnesium / aluminum mixture, magnesium z indium mixture, aluminum / aluminum oxide (A 1 2 0 3 ) Mixtures, alloys, lithium / aluminum mixtures, rare earth metals and the like.
- a mixture of an electron injectable metal and a second metal which is a stable metal having a larger work function than this such as a magnesium Z silver mixture, Magnesium Z aluminum mixture, magnesium
- the cathode can be manufactured by forming a thin film from these electrode substances by a method such as vapor deposition and sputtering. Further, the sheet resistance as the cathode is preferably several hundreds or less, and the film thickness is usually selected in the range of 10 nm to 5 ⁇ m, preferably in the range of 50 to 200 nm. Note that if either the anode or the cathode of the organic EL element is transparent or translucent in order to transmit the emitted light, the emission luminance is advantageously improved.
- a transparent or translucent cathode can be manufactured by manufacturing the above metal on the cathode with a thickness of 1 to 20 nm and then manufacturing the conductive transparent material mentioned in the description of the anode on the cathode. By applying this, both anode and cathode are transparent Device can be manufactured.
- Injection layer >>: electron injection layer, hole injection layer
- the injection layer is provided as needed, and has an electron injection layer and a hole injection layer, and exists between the anode and the light emitting layer or the hole transport layer, and between the cathode and the light emitting layer or the electron transport layer as described above. You may let it.
- the injection layer is a layer provided between the electrode and the organic layer to reduce the driving voltage and improve the light emission luminance, and is referred to as “the organic EL device and the forefront of its industrialization (January 30, 1990). The details are described in Vol. 2, Chapter 2, “Electrode Materials” (pages 123 to 166) of “N.T. There is an electron injection layer (one cathode buffer).
- anode buffer (hole injection layer) is disclosed in Japanese Patent Application Laid-Open Nos. 9-54979, 9-260600, 8-28869, etc. Details are described. Specific examples include one layer of phthalocyanine buffer represented by copper phthalocyanine, one layer of oxide buffer represented by vanadium oxide, one layer of amorphous carbon buffer, and conductive materials such as poly (aniline) (emeraldine) and polythiophene. One example is a polymer buffer layer using a polymer.
- cathode buffer electro injection layer
- a metal buffer—layer represented by platinum, aluminum, etc. a layer of an alkali metal compound represented by lithium fluoride, an alkaline earth metal compound represented by magnesium fluoride, etc. Buffer layer, aluminum oxide JP2004 / 005621
- An oxide buffer layer typified by 40 mm is exemplified. It is desirable that the buffer layer (injection layer) is a very thin film, and its thickness is 0.1 nn! Depending on the material. A range of 55 ⁇ m is preferred.
- ⁇ blocking layer >>: hole blocking layer, electron blocking layer
- the blocking layer is provided as required in addition to the basic constituent layers of the organic compound thin film.
- the hole blocking layer is an electron transporting layer in a broad sense, and is made of a hole blocking material having a function of transporting electrons and having a very small ability to transport holes.
- the hole blocking layer blocks holes while transporting electrons. As a result, the recombination probability of electrons and holes can be improved.
- the hole blocking layer of the organic EL device of the present invention is provided adjacent to the light emitting layer.
- the hole blocking material of the hole blocking layer As a result, an organic EL device having higher luminous efficiency can be obtained. Furthermore, the service life can be further extended.
- an electron blocking layer is a hole transporting layer in a broad sense, and is made of a material that has a function of transporting holes and has an extremely small ability to transport electrons, and blocks electrons while transporting holes. This can improve the probability of recombination between electrons and holes.
- the light-emitting layer according to the present invention is injected from an electrode or an electron transport layer or a hole transport layer. This is a layer that emits light by recombination of incoming electrons and holes, and the light-emitting portion may be in the light-emitting layer or at the interface between the light-emitting layer and an adjacent layer.
- the light-emitting layer of the organic EL device of the present invention preferably contains a host compound and a phosphorescent compound (also referred to as a phosphorescent compound) shown below. It is preferable to use the material for an organic EL device of the present invention or the compound of the present invention. Thereby, the luminous efficiency can be further increased. Further, as the host compound, the above-mentioned material for an organic EL device of the present invention or a compound other than the compound of the present invention may be contained.
- the host compound is defined as a compound contained in the light emitting layer and having a phosphorescence quantum yield of phosphorescence at room temperature (at 25) of less than 0.01 at room temperature (at 25). .
- a plurality of known host compounds may be used in combination.
- a plurality of host compounds it is possible to adjust the transfer of electric charges, and it is possible to increase the efficiency of the organic EL device.
- a plurality of kinds of phosphorescent compounds it is possible to mix different luminescence, and thus, it is possible to obtain an arbitrary luminescent color.
- white light emission is possible, and it can be applied to lighting and backlighting.
- the light emitting layer may further contain a host compound having a maximum fluorescence wavelength as a host compound.
- a host compound having a fluorescence maximum wavelength is one having a high fluorescence quantum yield in a solution state.
- the fluorescence quantum yield is preferably 10% or more, particularly preferably 30% or more.
- Specific examples of host compounds having a fluorescence maximum wavelength include coumarin dyes, pyran dyes, cyanine dyes, croconium dyes, squarium dyes, and oxobe dyes.
- fluorescein dyes fluorescein dyes
- oral damine dyes pyridium dyes
- perylene dyes pyridium dyes
- stilbene dyes stilbene dyes
- polythiophene dyes and the like.
- the fluorescence quantum yield can be measured by the method described in Spectroscopy II, pp. 362 (1992 edition, Maruzen) of the 4th Ed.
- the material used for the light emitting layer (hereinafter, referred to as a light emitting material) preferably contains a phosphorescent compound at the same time as containing the above host compound. Thereby, an organic EL device having higher luminous efficiency can be obtained.
- the phosphorescent compound according to the present invention is a compound that emits light from an excited triplet, emits phosphorescence at room temperature (25 ° C.), and has a phosphorescence quantum yield of 25 It is a compound of 0.01 or more at ° C.
- the phosphorescence quantum yield is preferably at least 0.1.
- the phosphorescence quantum yield can be measured by the method described in Spectroscopy I I, pp. 398 (1992 edition, Maruzen) of the 4th edition of Experimental Chemistry Lecture 7.
- the phosphorescence quantum yield in a solution can be measured using various solvents, but the phosphorescent compound used in the present invention only needs to achieve the above-mentioned phosphorescence quantum yield in any of the solvents.
- Phosphorescent compounds emit light in two types, in principle. One is that carrier recombination occurs on the host compound to which carriers are transported, and the excited state of the host compound is generated.
- An energy transfer type in which light is emitted from a phosphorescent compound by transfer to a photoluminescent compound, and the other is that the phosphorescent compound becomes a carrier trap, and carrier recombination occurs on the phosphorescent compound to cause phosphorus
- It is a carrier trap type in which light emission from a light-emitting compound is obtained. In any case, the energy of the excited state of the phosphorescent compound is 04005621
- the condition is that the energy is lower than that of the excited state.
- the phosphorescent compound can be appropriately selected from known compounds used for the light emitting layer of the organic EL device.
- the phosphorescent compound used in the present invention is preferably a complex compound containing a metal belonging to Groups 85 to 10 in the periodic table of elements, and more preferably an iridium compound, an osmium compound, or a platinum compound. (Platinum complex compounds) and rare earth complexes, and among them, the most preferred is a iridium compound.
- the maximum phosphorescent emission wavelength of the phosphorescent compound is not particularly limited, and in principle, the central metal, the ligand, the substituent of the ligand, and the like are selected. Although the obtained emission wavelength can be changed, it is preferable that the phosphorescent emission wavelength of the phosphorescent compound has a maximum phosphorescence emission wavelength of 380 to 480 nm. With such an organic EL device emitting blue phosphorescent light or an organic EL device emitting white phosphorescent light, the luminous efficiency can be further enhanced.
- step 6 The emission color of the organic EL device of the present invention or the compound of the present invention is shown in FIG. 4.1 on page 108 of “New Edition of Color Science Handbook” (edited by The Japan Society of Color Science, Tokyo University Press, 1998).
- step 6 the color is determined by applying the result measured with the spectral radiance meter CS-10000 (Minolta) to the CIE chromaticity coordinates.
- the light-emitting layer can be formed by forming a film of the above compound by a known thinning method such as a vacuum evaporation method, a spin coating method, a casting method, an LB method, and an ink jet method.
- the thickness of the light emitting layer is not particularly limited, but is usually 5 nm to 5 5 m, preferably One
- the light-emitting layer may have a single-layer structure composed of one or more of these phosphorescent compounds and host compounds, or a laminated structure composed of a plurality of layers having the same composition or different compositions. Is also good.
- the hole transport layer is made of a hole transport material having a function of transporting holes.
- a hole injection layer and an electron blocking layer are also included in the hole transport layer.
- the hole transport layer may be provided as a single layer or a plurality of layers.
- the hole transporting material has any of hole injection or transport and electron barrier properties, and may be any of an organic substance and an inorganic substance.
- triazole derivatives oxaziazole derivatives, imidazole derivatives, polyarylalkyl derivatives, pyrazoline derivatives and pyrazoopene derivatives, phenylenediamine derivatives, arylamine derivatives, amino substitution derivatives
- Oxazole derivatives styryl anthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline-based copolymers, and conductive high molecular weight oligomers, especially thiophenoligoma.
- hole transporting material those described above can be used, but it is preferable to use a porphyrin compound, an aromatic tertiary amine compound and a styrylamine compound, particularly an aromatic tertiary amine compound. .
- aromatic tertiary amine compounds and styrylamine compounds include N, N, ⁇ ', N'-tetraphenyl 4,4'-diaminophenyl; ⁇ , ⁇ '-diphenyl ⁇ , ⁇ ' Bis (3-methylphenyl) -1- [1,1'-biphenyl-14,4'-diamine (TPD); 2,2-bis (4-di-p-tolylamine 2004/005621
- the hole transport layer is formed by applying the above hole transport material to, for example, a vacuum evaporation method, a spin coat method, It can be formed by thinning the film by a known method such as a casting method, a printing method including an ink jet method, and an LB method.
- the thickness of the hole transport layer is not particularly limited, but is usually about 5 nm to 5 jam, and preferably 5 nm to 200 nm.
- This hole transport layer may have a single-layer structure composed of one or more of the above materials.
- the electron transport layer is made of a material having a function of transporting electrons.
- the electron transport layer includes an electron injection layer and a hole blocking layer.
- the electron transport layer can be provided as a single layer or a plurality of layers.
- an electron transport material also serving as a hole blocking material used for the electron transport layer adjacent to the light emitting layer on the cathode side is injected from the cathode.
- Any material may be used as long as it has a function of transmitting the transferred electrons to the light-emitting layer, and any material can be selected from conventionally known compounds.
- a nitro-substituted fluorene derivative diphenyl
- examples thereof include a ruquinone derivative, a thiopyrandioxide derivative, a sulfoimide, a fluorenylidenemethane derivative, an anthraquinodimethane and an anthracene derivative, and an oxadiazole derivative.
- a thiadiazole derivative in which an oxygen atom of the oxaziazole ring is substituted with a sulfur atom, and a quinoxaline derivative having a quinoxaline ring known as an electron-withdrawing group may also be used as the electron transport material. it can.
- a polymer material in which these materials are introduced into a polymer chain or a polymer material in which these materials are used as a polymer main chain, can also be used.
- metal complexes of 8-quinolinol derivatives such as tris (8-quinolinol ⁇ PT / JP2004 / 005621
- metal free or metal phthalocyanine, or a metal phthalocyanine whose terminal is substituted with an alkyl group ⁇ sulfonic acid group or the like can be preferably used as the electron transport material.
- the distyrylpyrazine derivative exemplified as a material for the light emitting layer can be used as an electron transporting material, and like the hole injection layer and the hole transporting layer, n-type Si, n-type SiC, etc.
- Inorganic semiconductors can also be used as electron transport materials.
- the electron transport layer can be formed by thinning the above electron transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an inkjet method, and an LB method. .
- the thickness of the electron transport layer is not particularly limited, but is usually about 5 nm to 5 nm, preferably 5 nm to 200 nm.
- the electron transport layer may have a single-layer structure composed of one or more of the above materials.
- Substrate also called substrate, substrate, support, etc.
- the organic EL device of the present invention is preferably formed on a substrate.
- the substrate of the organic EL device of the present invention is not particularly limited in the type of glass, plastic, and the like, and is not particularly limited as long as it is transparent, but preferably used substrates include, for example, glass, quartz, and the like.
- a particularly preferred substrate is a resin film that can provide flexibility to the organic EL device.
- the resin film examples include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyester sulphone (PES), polyester terimide, polyether ether ketone, and polyphenylene sulfide. And polycarbonate, polycarbonate, polycarbonate (PC), cellulose triacetate (TAC), cellulose acetate propionate (CAP), and the like. On the surface of the resin film, an inorganic or organic film or a hybrid film of both of them may be formed.
- the organic electroluminescence device of the present invention preferably has an external extraction efficiency at room temperature of light emission of 1% or more, more preferably 5% or more.
- the external extraction quantum efficiency (%) the number of photons emitted to the outside of the organic EL device / the number of electrons flowing to the organic EL device ⁇ 100.
- a hue improving filter such as a color filter or the like may be used in combination, or a color conversion filter for converting the emission color of the organic EL element into multiple colors using a phosphor may be used in combination.
- the zimax of light emission of the organic EL element is preferably 480 nm or less.
- a thin film made of a desired electrode material for example, a material for an anode is deposited or sputtered on a suitable substrate so as to have a thickness of 1 m or less, preferably 10 to 200 nm.
- the anode is formed by a method such as tarling.
- organic compound thin films such as a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a hole blocking layer, which are organic EL element materials, are formed thereon.
- a method of thinning the organic compound thin film there are a vapor deposition method and a wet process (spin coating method, casting method, ink jet method, printing method) and the like as described above, but a uniform film is easily obtained. From the viewpoint that holes are hardly generated, a vacuum deposition method, a spin coating method, an ink jet method, and a printing method are particularly preferable. Further, a different film forming method may be applied to each layer.
- the deposition conditions may vary due to kinds of materials used, generally boat temperature 5 0 ⁇ 4 5 0 ° C, vacuum degree of 1 0- 6 ⁇ ; L 0 - 2 .
- a thin film made of a cathode material is formed thereon to a thickness of 1 m or less, preferably in the range of 50 to 200 nm, for example, by a method such as vapor deposition or sputtering.
- the desired organic EL device can be obtained by forming the cathode and providing the cathode. In the production of this organic EL device, it is preferable to consistently produce from the hole injection layer to the cathode by one evacuation, but it is also possible to take it out in the middle and apply a different film forming method. At that time, it is necessary to consider that the work is performed in a dry inert gas atmosphere.
- a shadow mask is provided only when a light emitting layer is formed, and since other layers are common, patterning such as a shadow mask is unnecessary.
- the film can be formed by the method, ink jet method, printing method, etc. P2004 / 005621
- the method is not particularly limited, but is preferably a vapor deposition method, an ink jet method, or a printing method.
- a vapor deposition method e.g., a vapor deposition method, an ink jet method, or a printing method.
- an evaporation method e.g., a vapor deposition method, an ink jet method, or a printing method.
- the cathode, the electron injection layer, the electron transport layer, the light emitting layer, the hole transport layer, the hole injection layer, and the anode in this order.
- a DC voltage is applied to the multicolor display device obtained in this manner, light emission can be observed by applying a voltage of about 2 to 40 V with the anode having a polarity and the cathode having one polarity.
- an AC voltage may be applied.
- the waveform of the applied alternating current may be arbitrary.
- the display device of the present invention can be used as a display device, a display, and various light emission light sources.
- display devices and displays full-color display is possible by using three types of organic EL devices that emit blue, red, and green light.
- Display devices and displays include televisions, personal computers, mobile devices, AV devices, teletext displays, and information displays in cars.
- the driving method may be either a simple matrix (passive matrix) method or an active matrix method.
- Honkiaki's lighting systems include home lighting, car interior lighting, backlights for watches and LCDs, signboard advertisements, traffic lights, light sources for optical storage media, light sources for electrophotographic copiers, light sources for optical communication processors, and optical sensors.
- the present invention is not limited to this.
- the organic EL device according to the present invention may be used as an organic EL device having a resonator structure.
- the purpose of using the organic EL device having such a resonator structure is as follows: a light source of an optical storage medium, a light source of an electrophotographic copying machine, a light source of an optical communication processor, a light source of an optical sensor, and the like. But not limited thereto.
- laser oscillation may be used for the above purpose.
- the organic EL device of the present invention may be used as a kind of lamp for lighting or exposure light source, a projection device of a type for projecting an image, or directly recognizing a still image or a moving image. It may be used as a type of display device (display).
- the driving method may be either a simple matrix (passive matrix) method or an active matrix method.
- a full-color display device can be manufactured by using three or more kinds of the organic EL devices of the present invention having different emission colors.
- FIG. 1 is a schematic diagram illustrating an example of a display device including an organic EL element.
- FIG. 2 is a schematic view of a display such as a mobile phone for displaying image information by light emission of an organic EL element.
- the display 1 includes a display unit A having a plurality of pixels, a control unit B that performs image scanning of the display unit A based on image information, and the like.
- the control unit B is electrically connected to the display unit A, sends a scanning signal and an image data signal to each of a plurality of pixels based on image information from the outside, and scans with the scanning signal.
- the pixels of each line emit light sequentially according to the image data signal, perform image scanning, and display image information on the display unit A.
- FIG. 2 is a schematic diagram of the display unit A.
- the display unit A has a wiring unit including a plurality of scanning lines 5 and data lines 6 and a plurality of pixels 3 on a substrate.
- the main members of the display unit A will be described below.
- FIG. 2 shows a case where the light emitted from the pixel 3 is extracted in the white arrow direction (downward).
- the scanning lines 5 and the plurality of data lines 6 in the wiring portion are each made of a conductive material, and the scanning lines 5 and the data lines 6 are orthogonal to each other in a grid pattern, and are connected to the pixels 3 at orthogonal positions (for details, refer to FIG. Not shown).
- the pixel 3 When a scanning signal is applied from the scanning line 5, the pixel 3 receives an image data signal from the data line 6, and emits light according to the received image data.
- Full color display is possible by appropriately arranging pixels in the red, green, and blue light emission colors on the same substrate.
- FIG. 3 is a schematic diagram of a pixel.
- the pixel includes an organic EL element 10, a switching transistor 11, a driving transistor 12, a capacitor 13, and the like.
- a full color display can be performed by using red, green, and blue light emitting organic EL elements as the organic EL elements 10 for a plurality of pixels and arranging them on the same substrate.
- an image data signal is applied from the control unit B to the drain of the switching transistor 11 via the data line 6.
- a scanning signal is applied from the control unit B to the gate of the switching transistor 11 via the scanning line 5.
- the driving of the switching transistor 11 is turned on, and the image data signal applied to the drain is transmitted to the gate of the capacitor 13 and the gate of the driving transistor 12.
- the capacitor 13 is charged in accordance with the potential of the image data signal, and the driving of the drive transistor 12 is turned on.
- the drive transistor 12 has a drain connected to the power supply line 7, a source connected to the electrode of the organic EL element 10, and a power supply line corresponding to the potential of the image data signal applied to the gate. A current is supplied from 7 to the organic EL element 10.
- the driving of the switching transistor 11 is turned off. However, even if the driving of the switching transistor 11 is turned off, the capacitor 13 holds the potential of the charged image data signal, so that the driving of the driving transistor 12 is kept on and the next scanning signal is applied. The light emission of the organic EL element 10 continues until the operation is performed.
- the driving transistor 12 is driven according to the potential of the next image data signal synchronized with the scanning signal, and the organic EL element 10 emits light.
- the light emitted from the organic EL element 10 is generated by providing a switching transistor 11 and a drive transistor 12 which are active elements to the organic EL element 10 of each of the plurality of pixels, so that each of the plurality of pixels 3
- the organic EL element 10 emits light.
- Such a light emission method is called an active matrix method.
- the light emission of the organic EL element 10 may be light emission of a plurality of gradations by a multivalued image data signal having a plurality of gradation potentials, or light emission of a predetermined light emission amount by a binary image data signal. Or off.
- the potential of the capacitor 13 is maintained until the next scanning signal is applied. Or discharge immediately before the next scanning signal is applied.
- the present invention not only the active matrix method described above, but also a passive matrix light emission drive in which the organic EL element emits light in accordance with the data signal only when the scanning signal is scanned may be used.
- FIG. 4 is a schematic diagram of a display device using a passive matrix method.
- a plurality of scanning lines 5 and a plurality of image data lines 6 are provided in a lattice shape so as to face each other with the pixel 3 interposed therebetween.
- the pixels 3 connected to the applied scanning line 5 emit light according to the image data signal.
- the passive matrix method there is no active element in the pixel 3, and the manufacturing cost can be reduced.
- the organic EL material according to the present invention can be applied to an organic EL element that emits substantially white light as a lighting device.
- a plurality of emission colors are emitted simultaneously by a plurality of emission materials, and white emission is obtained by mixing colors.
- white emission is obtained by mixing colors.
- a combination of a plurality of emission colors a combination containing three emission maximum wavelengths of the three primary colors of blue, green, and blue may be used, or two combinations using complementary colors such as blue and yellow, and blue-green and orange may be used. It may be one containing the emission maximum wavelength.
- a combination of light-emitting materials for obtaining a plurality of emission colors includes a combination of a plurality of phosphorescent or fluorescent light-emitting materials (light-emitting dopants), a fluorescent or phosphorescent light-emitting material, Any combination of a dye material that emits light from the light-emitting material as excitation light may be used.
- a method in which a plurality of light-emitting dopants are combined is preferable.
- the layer structure of the organic EL device for obtaining multiple emission colors A method in which a plurality of light-emitting dopants are present in one light-emitting layer, a method in which a plurality of light-emitting layers are present, and a method in which a dopant having a different light emission wavelength is present in each light-emitting layer, and light is emitted at different wavelengths. There is a method of forming minute pixels in a matrix.
- a patterning may be performed by a metal mask-ink jet printing method at the time of film formation.
- a metal mask-ink jet printing method When patterning, only the electrode may be patterned, the electrode and the light emitting layer may be patterned, or the entire element layer may be patterned.
- the platinum according to the present invention is adjusted so as to be compatible with a wavelength range corresponding to CF (color filter) characteristics.
- Any complex luminescent material may be selected and selected from known luminescent materials and whitened by combining them.
- the light-emitting organic EL element of the present invention can be used as a kind of lamp such as a home light, a vehicle light, and an exposure light as various light sources and lighting devices. It is also useful for display devices such as backlights of liquid crystal display devices.
- the pressure in the vacuum chamber was reduced to 4 ⁇ 10-4 Pa, and the heating boat containing the a-NPD was energized and heated, and vapor-deposited on the transparent support substrate at a vapor deposition rate of 0.1 nmZ second.
- a hole transport layer was provided.
- the heating boat containing Exemplified Compound 39 and Ir-11 was energized and heated, and was deposited on the hole transport layer at a deposition rate of 0.1 Sum, second and 0.012 ⁇ m / second, respectively.
- a light emitting layer was provided by co-evaporation.
- the substrate temperature at the time of vapor deposition was room temperature.
- the heating boat containing B-Alq was energized and heated, and deposited on the light emitting layer at a deposition rate of 0.1 nm / sec to provide a hole blocking layer having a thickness of 10 nm.
- a 1 q 3 of containing and heated by supplying an electric current to the baud DOO, further having a film thickness of 40 nm was deposited on the electron transport layer at a deposition rate of 0. 1 nm / sec
- An electron transport layer was provided.
- the substrate temperature at the time of vapor deposition was room temperature.
- 0.5 nm of lithium fluoride and 110 nm of aluminum were deposited to form a cathode, thereby producing an organic EL device 111.
- the same method as that of the organic EL device 1-1 was used except that the exemplified compound 39 used as the host compound of the light emitting layer was replaced with a compound shown below to obtain a host compound.
- ⁇ 1 to 8 were prepared. The structure of the compound used above is shown below.
- the operation life of the organic EL device produced were measured 5 CTC constant, the initial luminance 1000 with a current giving cd / m 2 is half of the constant current drive to the initial brightness (500 cd / m 2) at time, As described below, evaluation was made based on a relative value when the comparative organic EL element 1-6 was set to 100.
- the luminance (cd / m 2 ) was determined using the luminance measured with a spectroradiometer CS-1000 (manufactured by Koniki Minolta Co., Ltd.).
- the quantum efficiency (%) taken out of the fabricated organic EL device when a constant current of 2.5 m AZcm 2 was applied at 23 ° C. in a dry nitrogen gas atmosphere was measured.
- the measurement was also performed using a spectral radiance meter CS-1000 (manufactured by Minolta).
- lO OmmX l O OmmX l As a positive electrode, lO OmmX l O OmmX l.
- ITO indium tin oxide
- the transparent support substrate provided with the ITO transparent electrode was subjected to ultrasonic cleaning with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
- This transparent support substrate was fixed to a substrate holder of a commercially available vacuum deposition apparatus, while 200 mg of NPD was placed in a molybdenum resistance heating boat, and Exemplified Compound 13 was placed in another molybdenum resistance heating boat.
- the pressure in the vacuum chamber was reduced to 4 ⁇ 10-4 Pa, and the heating boat containing ⁇ -NPD was energized and heated, and vapor-deposited on a transparent support substrate at a vapor deposition rate of 0.1 nm / sec.
- a hole transport layer was provided.
- the compound containing Exemplified Compound 13 and Ir-1 The heat boat was energized and heated, and the light emitting layer was formed by co-evaporation on the hole transport layer at a deposition rate of 0.2 nmZ second and 0.012 ⁇ m / second, respectively.
- the substrate temperature at the time of vapor deposition was room temperature.
- the heating boat containing Exemplified Compound 39 was energized and heated, and a 10 nm-thick hole blocking layer was formed by vapor deposition on the light emitting layer at a vapor deposition rate of 0.1 nm / sec. .
- a 1 q 3 of the heating volume heated by passing electricity to a preparative containing, further having a film thickness of 40 nm was deposited on the electron transport layer at a deposition rate of 0. 1 NMZ seconds
- An electron transport layer was provided.
- the substrate temperature at the time of vapor deposition was room temperature. Subsequently, 0.5 nm of lithium fluoride and 110 nm of aluminum were deposited to form a cathode, and an organic EL device 2-1 was produced.
- the same method as that of the organic EL device 2-1 was used except that the exemplified compound 39 used as a hole blocking material was replaced with the compound described below. 8 was produced.
- Example 2 In the same manner as in Example 1, the luminance, external extraction quantum efficiency, and driving life of the organic EL elements 2-1 to 2-8 were evaluated. The measurement result of the driving life was expressed as a relative value when the organic EL element 2-6 was set to 100. The results obtained are shown below.
- the EL device was the same as the blue light-emitting organic EL device produced in the same manner except that the phosphorescent compound of the organic EL device 2-4 of the present invention was replaced with Ir-11.
- the active matrix type full-color display device shown in Fig. 1 was fabricated by juxtaposing them on a substrate.
- FIG. 2 shows only a schematic diagram of the display section A of the manufactured full-color display device.
- a wiring portion including a plurality of scanning lines 5 and data lines 6 and a plurality of juxtaposed pixels 3 (pixels in a red region, pixels in a green region, pixels in a blue region, etc.)
- the scanning line 5 and the plurality of data lines 6 in the wiring portion are each made of a conductive material, and the scanning line 5 and the data line 6 are orthogonal to each other in a grid pattern and are connected to the pixel 3 at orthogonal positions ( Details are not shown).
- the plurality of pixels 3 are driven by an active matrix method provided with an organic EL element corresponding to each emission color, a switching transistor and an active transistor as active elements, and a scanning signal is transmitted from a scanning line 5.
- a material for an organic electroluminescence element having a high luminous efficiency an organic electroluminescence element using the material for an organic electroluminescence element, a lighting device, and a display device. Furthermore, a material for an organic electroluminescence element having a long life, an organic electroluminescence element using the material for an organic electroluminescence element, a lighting device, a display device, and a novel compound suitably used as the organic EL element material could be provided.
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Abstract
Description
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JP2005505745A JP4635870B2 (ja) | 2003-04-23 | 2004-04-20 | 有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
EP20040728448 EP1617710B1 (en) | 2003-04-23 | 2004-04-20 | Material for organic electroluminescent device, organic electroluminescent device, illuminating device and display |
US10/532,027 US7326475B2 (en) | 2003-04-23 | 2004-04-20 | Material for organic electroluminescent device, organic electroluminescent device, illuminating device and display |
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PCT/JP2004/005603 WO2004095889A1 (ja) | 2003-04-23 | 2004-04-20 | 有機エレクトロルミネッセンス素子及び表示装置 |
PCT/JP2004/005616 WO2004095890A1 (ja) | 2003-04-23 | 2004-04-20 | 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、照明装置、表示装置 |
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PCT/JP2004/005616 WO2004095890A1 (ja) | 2003-04-23 | 2004-04-20 | 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、照明装置、表示装置 |
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Cited By (6)
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JP2005340123A (ja) * | 2004-05-31 | 2005-12-08 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
JP2006156635A (ja) * | 2004-11-29 | 2006-06-15 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子及び表示装置 |
JP2007137829A (ja) * | 2005-11-18 | 2007-06-07 | Chemiprokasei Kaisha Ltd | 新規なトリアジン誘導体およびそれを含む有機エレクトロルミネッセンス素子 |
JP2011146743A (ja) * | 2011-04-14 | 2011-07-28 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子及び表示装置 |
JP2011193004A (ja) * | 2011-04-14 | 2011-09-29 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子及び表示装置 |
WO2018181370A1 (ja) * | 2017-03-28 | 2018-10-04 | 保土谷化学工業株式会社 | アザカルバゾール構造を有する化合物および有機エレクトロルミネッセンス素子 |
Also Published As
Publication number | Publication date |
---|---|
US20080088230A1 (en) | 2008-04-17 |
US7740955B2 (en) | 2010-06-22 |
JP4635869B2 (ja) | 2011-02-23 |
EP1617711A1 (en) | 2006-01-18 |
US7326475B2 (en) | 2008-02-05 |
JPWO2004095890A1 (ja) | 2006-07-13 |
EP1617710B1 (en) | 2015-05-20 |
EP1617710A1 (en) | 2006-01-18 |
EP1617711B1 (en) | 2016-08-17 |
JPWO2004095889A1 (ja) | 2006-07-13 |
JP4626515B2 (ja) | 2011-02-09 |
EP2236579B1 (en) | 2014-04-09 |
EP1617711A4 (en) | 2009-08-19 |
EP2236579A2 (en) | 2010-10-06 |
JPWO2004095891A1 (ja) | 2006-07-13 |
EP2236579A3 (en) | 2010-12-15 |
US7749619B2 (en) | 2010-07-06 |
JP4635870B2 (ja) | 2011-02-23 |
EP1617710A4 (en) | 2009-08-12 |
WO2004095889A1 (ja) | 2004-11-04 |
US20050249970A1 (en) | 2005-11-10 |
US20060121308A1 (en) | 2006-06-08 |
WO2004095890A1 (ja) | 2004-11-04 |
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