WO2005033118A1 - 配位金属化合物、有機エレクトロルミネッセンス素子用材料、発光性塗膜形成用材料及び有機エレクトロルミネッセンス素子 - Google Patents
配位金属化合物、有機エレクトロルミネッセンス素子用材料、発光性塗膜形成用材料及び有機エレクトロルミネッセンス素子 Download PDFInfo
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- WO2005033118A1 WO2005033118A1 PCT/JP2004/012427 JP2004012427W WO2005033118A1 WO 2005033118 A1 WO2005033118 A1 WO 2005033118A1 JP 2004012427 W JP2004012427 W JP 2004012427W WO 2005033118 A1 WO2005033118 A1 WO 2005033118A1
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- 239000000463 material Substances 0.000 title claims abstract description 124
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- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 3
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- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
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- 150000003219 pyrazolines Chemical class 0.000 description 1
- MCSKRVKAXABJLX-UHFFFAOYSA-N pyrazolo[3,4-d]triazole Chemical compound N1=NN=C2N=NC=C21 MCSKRVKAXABJLX-UHFFFAOYSA-N 0.000 description 1
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- MHOZZUICEDXVGD-UHFFFAOYSA-N pyrrolo[2,3-d]imidazole Chemical compound C1=NC2=CC=NC2=N1 MHOZZUICEDXVGD-UHFFFAOYSA-N 0.000 description 1
- QEIQICVPDMCDHG-UHFFFAOYSA-N pyrrolo[2,3-d]triazole Chemical compound N1=NC2=CC=NC2=N1 QEIQICVPDMCDHG-UHFFFAOYSA-N 0.000 description 1
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- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000002909 rare earth metal compounds Chemical class 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
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- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
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- 239000010703 silicon Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
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- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
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- 229910052712 strontium Inorganic materials 0.000 description 1
- PDGYMUBNWUUWEI-UHFFFAOYSA-N strontium zirconium Chemical compound [Sr].[Zr] PDGYMUBNWUUWEI-UHFFFAOYSA-N 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 125000006836 terphenylene group Chemical group 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- YGNGABUJMXJPIJ-UHFFFAOYSA-N thiatriazole Chemical compound C1=NN=NS1 YGNGABUJMXJPIJ-UHFFFAOYSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
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- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 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
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 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
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
- C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
- C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
- C08G61/125—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one oxygen atom in the ring
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
- 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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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
- H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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Definitions
- the present invention relates to a coordinating metal compound, a material for forming a luminescent coating film, a material for an organic electroluminescent element, and an organic electroluminescent element, and in particular, has a high luminous efficiency and stability under high-temperature storage.
- High organic EL element realizing it, excellent solubility in organic solvents, coordination metal compound, organic electro-luminescence element that can be used for organic electroluminescence element by simple wet film formation method as well as vacuum deposition
- the present invention relates to a material for a luminescence element and a material for forming a light-sensitive coating film.
- EL Organic electroluminescent devices
- EL emit fluorescent light by recombination energy of holes injected from an anode and electrons injected from a cathode by applying an electric field.
- This is a self-luminous element that uses the principle of emitting luminescent substances.
- C. W. Tang et al. Of Eastman's Kodak report on low-voltage driven organic EL devices using stacked devices (C. l Tang, SA Vanslyke, Applied Physics Letters, 5 1) Vol. 9, pp. 9, 1987), research on organic EL devices using organic materials as constituent materials has been actively conducted.
- the element structure of the organic EL element is a two-layer type of a hole transport (injection) layer and an electron transport / injection layer, or a hole transport (injection) layer, an emission layer, and an electron transport (injection).
- the three-layer type is well known. In order to increase the recombination efficiency of the injected holes and electrons in such a stacked structure device, the device structure and the formation method are devised.
- Examples of light emitting materials for organic EL devices include chelate complexes such as tris (8-quinolinolate) aluminum complex, coumarin derivatives, tetraphenylbutadiene derivatives, bisstyrylarylene derivatives, oxaziazole derivatives and the like.
- Luminescent materials are known, and it has been reported that they can emit light in the visible region from blue to red, and realization of a color display element is expected (for example, see JP-A-8-2).
- Japanese Patent Application Laid-Open No. 396555 Japanese Unexamined Patent Application Publication No. Hei 7-138591, Japanese Unexamined Patent Application Publication No. Hei 3-20289, etc.).
- the light emitting layer of the organic EL element high luminous efficiency is achieved by utilizing the excited singlet state and the triplet state of the organic phosphorescent material.
- electrons and holes recombine in an organic EL device, it is thought that singlet excitons and triplet excitons are produced in a ratio of 1: 3 due to the difference in spin multiplicity. Therefore, if phosphorescent light emitting materials are used, it is conceivable that the light emitting efficiency can be attained 3 to 4 times that of a device using only fluorescence.
- an organic EL device 3. an anode, a hole transport layer, an organic light emitting layer, and an electron transport layer (a hole blocking layer) are sequentially arranged so that a triplet excited state or a triplet exciton is not quenched.
- 4,4-N, N-dicarbazole bisenyl has been used as a host compound.
- this compound has a glass transition temperature of 110 ° C or less and further has a symmetry. Because it is too good, it tends to crystallize, and when subjected to a heat resistance test of the device, there is a problem that a short circuit or a pixel defect occurs.
- an iridium complex is used as the phosphorescent compound, and the light emitting layer is formed of a host compound in which the iridium complex is mixed at a certain ratio (several mass% or less).
- concentration quenching or concentration deactivation is disclosed in Japanese Patent Application Laid-Open No. H05-078655 and Japanese Patent Application Laid-Open No. H05-320363. This seems to be related to non-radiative transition due to multimerization reaction between the luminescent center materials or their surrounding materials. For this reason, many phosphorescent compounds could not be used for high efficiency, and the concentration had to be optimized.
- the present invention has been made to solve the above-mentioned problems, and has an organic EL device having high luminous efficiency, high stability under high-temperature storage, realizing the same, and coordination having excellent solubility in an organic solvent.
- An object is to provide a metal compound, a material for an organic EL device, and a material for forming a luminescent coating film.
- the present inventors have conducted intensive studies to achieve the above object.As a result, when a coordination metal compound having a ligand containing a spiro bond is used as a light emitting material, the association between molecules is suppressed, As a result, they have found that it is possible to produce an organic EL device having high luminous efficiency and high stability even under high-temperature storage, and have completed the present invention.
- this coordination metal compound has high solubility in organic solvents, and has become applicable to wet film formation processes such as spin coating.
- the present invention provides a coordination metal compound in which a ligand having a spiro bond is coordinated to at least one metal atom.
- the term “coordinating” means that a carbon atom and a metal atom bond are formed between a ligand and a metal atom.
- the loan pair of the heteroatom of the ligand forms a coordination bond with the metal atom.
- the present invention provides a material for an organic EL device, comprising at least one compound having a structure represented by the following general formula (1 ′):
- [ 'In, X, Y 1 and Y 2 are each independently a single bond, - CR equation (1)' R "-, one S i R 'R" -, - CO- or NR' - indicates, Q represents a carbon atom, a silicon atom or a germanium atom.
- Z represents a divalent group comprising a heavy metal complex.
- R 'and R ⁇ are a hydrogen atom, a substituted or unsubstituted aromatic group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms, and Alternatively, it represents a group selected from non-substituted alkyl groups having 1 to 50 carbon atoms.
- R i R 8 is each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, an alkenyl group, an alkynyl group, an alkoxy group, an alkylthio group, an amino group, an alkylamino group, a dialkyl Selected from an amino group or a heterocyclic group, and an aryl group having 6 to 50 carbon atoms, an aryloxy group, an arylthio group, an arylamino group, a diarylamino group or an alkylarylamino group. Represents a group.
- R 1 ! ⁇ 8 two adjacent substituents may be bonded to each other to form a ring structure.
- (Phos) is a divalent group formed by removing two of R 1 to R 8 in the general formula (1 ′).
- E 1 and E 2 each independently represent a hydrogen atom, a substituted or unsubstituted aromatic group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted aromatic group having 5 to 50 nuclear atoms Heterocyclic group, substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, substitution Or an unsubstituted aryloxy group having 5 to 50 nuclear atoms; a substituted or unsubstituted nuclear atom having 5 to 50 arylthio groups; a substituted or unsubstituted carbon atom having 1 to 50 carbon atoms.
- c ] to c 4 are a group selected from a substituted or unsubstituted alkylene group having 1 to 50 carbon atoms and a substituted or unsubstituted divalent arylene group having 6 to 50 carbon atoms. Show. pl to p4 are integers of 0 to 20 respectively.
- At least one of R 1 ! ⁇ 8 in the general formula (1 ′) is an aromatic group having 6 to 50 nuclear carbon atoms including a polymerizable group or a polymerizable group, and the general formula (1 ′)
- the present invention provides an organic EL device in which at least one organic thin-film layer having at least a light-emitting layer or a plurality of organic thin-film layers is sandwiched between a cathode and an anode; It is intended to provide an organic EL device containing a compound or a material for an organic EL device.
- the present invention further provides a luminescent coating film forming material comprising an organic solvent solution containing the coordinating metal compound or the organic EL device material, and the luminescent coating film forming material or the organic EL device material.
- An object of the present invention is to provide an organic EL device formed by the above method. BEST MODE FOR CARRYING OUT THE INVENTION
- the coordination metal compound of the present invention is a coordination metal compound obtained by coordinating at least one ligand having a spiro bond, and is a coordination metal compound represented by the following general formula (1). Is preferred.
- L, in the general formula (1) is a ligand represented by the following general formula (2).
- A is a group represented by any of the following general formulas (3) to (12).
- alkoxycarbonyl groups carboxyl groups, halogen atoms, cyano groups, nitro groups, hydroxy groups, etc., and may be bonded to each other to form a ring structure.
- a and b are each an integer of 0 to 4
- c, d, e, and f are each an integer of 2 to 4.
- Examples of the substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms for R include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, and 2-anthryl. 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 1-naphthacenyl group, 9- Naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-taphenyl-1-yl group, p —Taffeninole 3 —Innole group, p —Tafeninolene 2—Innole group, m—Tfenylinnole group
- Examples of the substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms of R include 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, virazinyl group, Pyrimidyl, pyridazyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-in Drill base, 5—In drill base, 6—In drill base, 7—In drill base, 1—Isoin drill base, 2—Isoin drill base, 3—Isoin drill base, 4—Isoin drill base, 5 —Isoin drill, 6—Isoin drill, 7—Isoin drill, 2—furyl, 3-furyl, 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl Group, 5-benzofuranyl group, 6-benzofuranyl group, 7-benzofurany
- Examples of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms for R include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, and a Soptyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptinole group, n-octyl group, hydroxymethyl group, 1-hydroxyxetinole group, 2-hydroxyxethyl group, 2-hydridyl group Loxyisobutyl, 1,2-dihydroxyshethyl, 1,3-dihydroxyisopropyl, 2,3-dihydroxy-t-butyl, 1,2,3-trihydroxypropyl, Chloromethyl, 1-chloroethyl, 2-chloroethyl, 2-chloroisobutyl, 1,2-dichloroe
- 2-Aminoethyl group 2-Aminoisobutyl group, 1,2-Diaminopropyl group, 1,3-Diaminopropyl group, 2,3-Diaminot-butyl group, 1,2,
- the substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms for R is a group represented by OY, and examples of Y include a methyl group, an ethyl group, a propyl group, and an iso group.
- Examples of the substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms for R include a benzinole group, a 1-phenylenoletinol group, a 2-phenylenoletinol group, and a 1-phenylinolesopropyl group. , 2-phenylisopropyl, phenyl t-butyl, Q!
- the substituted or unsubstituted aryloxy group having 5 to 50 nuclear atoms of R is a group represented by 1 OY ′, and examples of Y ′ include a phenyl group, a 1-naphthyl group, 2-naphthyl, 1-anthryl, 2-anthryl, 91-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl Ryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylenolinole group, 3 — biphenylinoleyl group, 4 — biphenylinoleyl group, p — terphenyl-1-yl group, p—taphenylene 3 — inolele group,
- 8-Fenanthroline-1-yl group 2,8-Fenanthroline-1-3-inole group, 2,8-Fenanthroline-1-4-inole group, 2,8-Fenanthroline-1-5-inole group Group, 2,8-phenanthroline-1 6-inole group, 2,8-phenanthroline-1 7-yl group, 2,8-phenanthroline-1 9-yl group, 2,8-phenanthroline 1 10-isole group, 2,7-phenanthroline 1-inole group, 2,7-phenanthroline 1-3-yl group, 2,7-phenanthroline 1-4-inole group, 2, 7 1-Fenanthroline-5-yl group, 2,7-Fenanthroline-1-6-yl group, 2,7-Fenanthroline-18-yl group, 2,7-Fenanthroline-1 9-yl group 1,2,7-phenanthroline-10-yl group, 1-phenazinyl group, 2-phenazinyl group, 1-phenothiazinyl group
- the substituted or unsubstituted arylthio group having 5 to 50 nuclear atoms for R is represented by —S Y ′, and examples of Y ′ are the same as those described above.
- the substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms for R is represented by —COO Y, and examples of Y include the same as those described above.
- V is a single bond or one CR.
- Ro and Ro ′ each independently represent a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 5 to 50 aromatic atoms, A cyclic group or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
- specific examples of the aromatic hydrocarbon group, the aromatic heterocyclic group and the alkyl group of Ro ' include those similar to the aforementioned R.
- E represents a cyclic structure represented by a circle surrounding the symbol E, wherein the substituted or unsubstituted carbon atom has 3 to 6 carbon atoms and a carbon atom is replaced by a nitrogen atom.
- aromatic hydrocarbon residue and the aromatic heterocyclic group residue include those described above for R, which are divalent residues having the same carbon number.
- examples of cycloalkane residues having 3 to 6 carbon atoms and a carbon atom which may be replaced by a nitrogen atom include cyclopropane, cyclobutane, cyclopropane, cyclohexane, cycloheptane, and pyrrolidine.
- divalent residues such as gin, piperidine, and piperazine.
- Q is an atomic group forming a cyclic structure, and examples thereof include an ethylene group, a propylene group, an n-butylene group, an n-pentylene group, and an n-hexylene group.
- Alkylene groups, and groups in which at least one of the carbon atoms of these alkylene groups is replaced by a nitrogen atom or an oxygen atom to form a heterocyclic ring, etc., may be substituted, and may have a substituent.
- the groups may be combined with each other to form a saturated or unsaturated ring.
- Z is one CR. Ro'—, one S i R. Ro 'one or one Ge Ro Ro'- (Ge is a germanium atom, R. and Ro' are the same as described above).
- the group represented by the general formula (3) is preferably a group represented by any one of the following general formulas (22) to (25).
- R, a, b are as defined above, R to R 8 are the same as those described in each said R.
- the group represented by the general formula (7) is preferably a group represented by the following general formula (30).
- R, V, a, and b are the same as described above.
- AA 4 each independently represent —CR ′ R, —S i R ′ R ′′ —, — ⁇ —, —NR ′ one, one CO—.
- R ', R'' is as defined above R, and R' R "may be the same or different.
- at least one of A ⁇ to A 4 those two adjacent, Each represented by —CR′R ′′ —and adjacent R ′s, R ′ ′s or R ′ and R ′ ′ are saturated or unsaturated bonds, and have a cyclic structure of 4 to 50 carbon atoms. May be formed.
- w is an integer of 1 to 10; Further, examples of the group represented by the general formula (30) are shown below, but are not limited thereto.
- the group represented by the general formula (8) is preferably a group represented by the following general formula (31).
- R, V , a, b, Ai ⁇ A 4, w ⁇ is because, the same as the 0 '
- the group represented by the general formula (9) is preferably a group represented by any one of the following general formulas (32) to (35).
- the group represented by the general formula (10) is preferably a group represented by any one of the following general formulas (36) to (39).
- R, a, b, c the same, to R S are the same as those described using each of the R.
- the group represented by the general formula (11) is preferably a group represented by the following general formula (40). '
- R, V , a, b, Aa ⁇ A 4, w, e is the same as the above.
- the group represented by the general formula (12) is preferably a group represented by the following general formula (41).
- R, V , a, b, A ⁇ A 4, w, f is the same as the above.
- B is a group represented by the following general formulas (13) to (15), and may be used alone or in combination.
- q is an integer between 0 and 20 (preferably between 0 and 10).
- R, V, E, Z, Q, a and b are the same as described above.
- the groups represented by the general formulas (13) and (14) are preferably groups represented by the following general formulas (42) and (43), respectively.
- R, V , a, b, Ax ⁇ A 4, w are as defined above.
- the group represented by the general formula (15) is preferably a group represented by the following general formula (44).
- R is the same as described above.
- C is a substituted or unsubstituted alkylene group having 150 carbon atoms or a substituted or unsubstituted aromatic hydrocarbon group having 650 carbon atoms, and C may be the same or different.
- p is an integer of 0 20 (preferably 0 to: I 0).
- Examples of the above-mentioned substituted or unsubstituted alkylene group having 150 carbon atoms include a methylene group, an ethylene group, a propylene group, an isopropylene group, an n-butylene group, an s-butylene group, an isobutylene group, and the like.
- Examples of the above-mentioned substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms include the following.
- the site D coordinated to a metal atom is preferably a group obtained by removing a hydrogen atom from a molecule represented by the following general formula (20).
- Q and Q 2 each independently represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms, or a derivative thereof.
- the and the one least also one Q 2 ' is a benzene ring or a derivative thereof, either to form a first metal atom bonded the metal atom M and the carbon atom of Qi and Q 2, the other coordination bond
- Aromatic hydrocarbon group Qi and Q 2 is a aromatic heterocyclic group, the same ones as described for R can be mentioned.
- Z 3 is a single bond, —C Ro Ro′—, —S i Ro Ro′—, one O—, one CO— or one NRo (R and Ro ′ are the same as described above).
- D is preferably a substituted or unsubstituted fuynylpyridyl group.
- a and / or B include at least one structure having a spiro skeleton.
- A is a group selected from the following general formulas (5), (6) and (22) to (41);
- B is preferably a group selected from the following general formulas (42) to (44).
- L in the general formula (1) is preferably a ligand represented by the following general formula (16).
- A is a group represented by any of the following general formulas (3) to (12), and a plurality of As may be the same or different.
- R, V, E, Q, Z and a to f in the general formulas (3) to (12) are the same as described above.
- C in the general formula (16) is the same as described above, and a plurality of Cs may be the same or different.
- s, t and u are each an integer of 0 to 20 (preferably 0 to 10).
- R, V, Z, Q, a and b are the same as described above.
- the group represented by the general formula (17) is preferably a group represented by the following general formula (45). ⁇
- R, a and b are the same as above.
- the group represented by the general formula (18) is preferably a group represented by the following general formula (46).
- R, V , a, b, Ax ⁇ 4, w is further the same as defined above, illustrates the general formula (4 5) and examples of the group (4 6) below However, it is not limited to these.
- the site D coordinated to a metal atom is preferably a group obtained by removing a hydrogen atom from the molecule represented by the general formula (20).
- D is preferably a substituted or unsubstituted phenylpyridyl group.
- a and / or at least one or more structures having a spiro skeleton are included.
- A is a group selected from the following general formulas (22) to (41), and B is the following general formula (45) Or (46) is preferred.
- X is an integer from 1 to the valence of the metal atom M
- y is an integer from 0 to 4
- z is an integer from 0 to 4.
- M is iridium (Ir), platinum (Pt), osmium (Os), rhodium (Rh), rhenium (Re), palladium (Pd), A metal atom of ruthenium (R U ), tungsten (W), gold (A u) or silver (A g); Ir is preferred D ; and when y is 1 or more, a plurality of metal atoms M are the same But they may be different.
- P in the general formula (1) is a ligand that connects the metal atom M when y is 1 or more, and includes, but is not limited to, the following examples.
- L 2 in the general formula (1) is a ligand which coordinates to the metal atom M, and may be the same as the above L ⁇ .
- halogen atoms such as F, CI, Br, and I
- the ingredients body examples of L 2 are shown below, but the invention is not limited thereto.
- the material for an organic EL device of the present invention contains at least one compound having a structure represented by the following general formula (1 ′).
- X, ⁇ 1 and ⁇ 2 each independently represent a single bond, one CR'R "-, one SiR'R-, -C ⁇ - or NR'-, Q represents a carbon atom, a silicon atom or a germanium atom
- Z represents a divalent group composed of a heavy metal complex
- R ′ and R ⁇ represent a hydrogen atom and a substituted or unsubstituted nuclear carbon number of 6 to 50
- R 1 to R 8 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, an alkenyl group, an alkynyl group, an alkoxy group, an alkylthio group, an amino group, and an alkylamino group.
- Examples of Z include a divalent group formed by removing two hydrogen atoms from a metal complex represented by the following general formula (2 ′). ⁇ (L 1 ) n M-. (L 2 ) m (2 ′) In the formula (2 ′), L 1 is represented by the following general formula (3 ′) combining with Y] and Y 2 in the formula (1 ′). 1 shows a metal coordination unit represented.
- a 1 and A 2 each independently represent a substituted or unsubstituted aromatic group having 6 to 50 carbon atoms, and a substituted or unsubstituted nuclear atom having 5 to 50 carbon atoms. 50 aroma; ⁇ A group selected from heterocyclic groups, at least one of which is a phenyl group or a substituted phenyl group.
- B 1 is a single bond, one CR′R ′′ —, one SiR′R, one CO— or NR′—.
- R ′ and R ′′ are a hydrogen atom, a substituted or Unsubstituted aromatic group having 6 to 50 nuclear carbon atoms, substituted or unsubstituted nuclear atom having 5 to 50 aromatic heterocyclic groups, and substituted or unsubstituted alkyl having 1 to 50 carbon atoms Shows a group selected from groups.
- a particularly preferred metal coordination unit has the following structure.
- M represents a metal atom selected from Ir, Pt, Os, Rh, Re, Pd, Ru, W, Au, and Ag.
- a preferred metal atom is Ir (iridium).
- “L ⁇ ⁇ MJ means that L 1 coordinates to the metal atom M, and is selected from the following.
- the carbon atom of L 1 is bonded to the metal atom M, and an atom selected from N, O and S is coordinated to the metal atom M.
- coordination form particularly preferred are the following coordination forms, in which a carbon atom is bonded to a metal M and an N atom is coordinated to the metal M.
- L 2 is a ligand that coordinates to the metal, and may be the same as or different from L 1 .
- L 2 ⁇ M means that L 2 coordinates to the metal atom M, and is selected from the ⁇ bond of a nodogen atom or the following.
- the atom selected from the carbon atom of L 2 , ⁇ and ⁇ is bonded to the metal atom ⁇ , and the atom selected from ⁇ , ⁇ and S is coordinated to the metal atom ⁇ .
- L 2 is a halogen atom, an acetylacetone derivative represented by the following general formula, an 8-quinolinol derivative or a phenylpyridine derivative. Both are preferred.
- Shaku 11 ⁇ ! ⁇ 2 7 each independently represent a hydrogen atom, Shiano group, nitro group, halogen atom, substituted or unsubstituted alkyl group of indicated number 1-2 0 carbon atoms, an alkoxy group ', also the properly alkylsilyl group A group selected from the group consisting of an amino group, a substituted or unsubstituted amino group, and a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
- L 2 an acetylacetylone derivative, an 8-quinolinol derivative and a phenylpyridine derivative are preferred.
- n represents an integer of 1 to X (X: valence of metal), and m represents an integer of 0 to ( ⁇ n).
- Examples of the material for an organic EL device of the present invention include a material containing at least one compound represented by the following general formula (4 ′).
- (Phos) Is a divalent group formed by removing two of R 1 to R 8 in the general formula (1 ′).
- Z represents the general formula (1 ′). 2, is preferably.
- pl to p4 are each an integer of 0 to 20 and are preferably Is an integer from 0 to 5.
- Examples of the substituted or unsubstituted aromatic group having 6 to 50 nuclear carbon atoms represented by E 1 and E 2 include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl , 2-anthryl, 9-anthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, 1-naphthacenyl, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyreninole group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenylyl group, p-terfenolinole-4-inole group, p-terphenyl_3 Group, p-terphenyl 2- inole group, m-terphenyl 1-4-inole group, m-terphenyl 3- Nore group, m-terphenyl group, 2-yl group, o-tri
- Examples of the substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, virazinyl, pyrimidyl, Pyridazyl, 2-pyridinyl, 3-pyridinyl, 4-pyridinyl,
- 2-quinoxalinyl group 5-quinoxalinyl group, 6-quinoxalinyl group, 1-carbazolyl group, 2-rubazolyl group, 3-carbazolyl group, 4-rubazolyl group, 9-rubazolyl group, 1-phenanthridinyl group, 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group, 6-phenena 3-phenyl ninyl group, 7-phenidyl ridinyl group, 8-phenyl liginyl group, 9-phenidyl liginyl group, 10-phenidyl liginyl group, 1-ataridinyl group, 2-acrylidinyl group, 3-a Cridinyl group, 4-acrylidinyl group, 91-ataridinyl group, 1,7-phenanthroline-12-yl group, 1,7-phenanthroline-13-inole group, 1,7- 1,4,7-phenanthroline-5-y
- Examples of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group. —Butyl, n-pentyl, n—hexyl, n-heptyl. W 200
- n octynole group, hydroxymethyl group, 1-hydroxyxethyl group, 2-hydroxyxetinole group, 2-hydroxyisobutyl group, 1,2-dihydroxyxethyl group 1,3-dihydroxyisopropyl group, 2,3— Dihydroxyl t-butyl 1,2,3—Trihydroxypropyl, chloromethyl, 1-chloroethyl, 2-chloroethyl, 2-chloroisobutyl, 1 , 2-Dichloromethyl ethyl group, 1,3-Dichloromethylisopropyl group, 2,3-Dichloro-t-butyl group, 1,2,3-Trichloromethylpropyl group, bromomethyl group, 1 monobromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dipromo
- a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms is represented by OY
- Y include a methyl group, an ethyl group, a propyl group, an isopropyl group, an ⁇ -butyl group, an s-butyl group, an isobutyl group, a t-butyl group, and an n-pentyl group.
- An example of a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms is benzyl. Nore, 1-phenylethyl, 2-phenyl-, 1-phenylisopropyl, 2-phenyl-isopropyl, phenyl-tert-butyl, ⁇ -naphthylmethinole, ⁇ -naphthylethyl, 2- ⁇ -naphthylethyl group, 1 _ ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group, —naphthylmethyl group, 1——naphthylethyl group, 2-—naphthylethyl group, 1- ⁇ -naphthinoyl isopropyl group, 2 —; 3 — naphthylisopropyl group, 1 —pyrrolylmethyl group, 2
- a substituted or unsubstituted aryloxy group having 5 to 50 nuclear atoms is a group represented by —OY ′, and examples of Y ′ include a phenyl group and a 1-naphthyl group.
- Y ′ include a phenyl group and a 1-naphthyl group.
- the substituted or unsubstituted arylthio group having 5 to 50 nuclear atoms is a group represented by —S Y ′, and examples of Y ′ are the same as described above.
- a substituted or unsubstituted alkoxycarbonyl group having 1 to 50 carbon atoms is a group represented by 1COOY, and examples of Y are the same as described above.
- Examples of the substituted or unsubstituted alkylene group having 1 to 50 carbon atoms represented by C 1 to C 4 include a methylene group, an ethylene group, a propylene group, an isopropylene group, an n-butylene group, and an s-butylene group.
- Examples of the substituted or unsubstituted binary arylene groups having 6 to 50 carbon atoms represented by C 4 to C 4 include those having the following structures.
- a material for an organic EL device of the present invention a material containing two polymers (AB) described below can also be mentioned.
- At least one of R 1 to R 8 in the general formula (1 ′) is a polymerizable group or an aromatic group having a core carbon number of 6 to 50 and containing a polymerizable group. It contains a polymer formed by polymerizing or copolymerizing the compound represented by (1) or (2).
- the polymerizable group include a butyl group and an epoxy group.
- a preferred polymerizable group is a butyl group.
- Examples of the polymerization ⁇ : A are shown below, but the present invention is not limited by these exemplified compounds.
- Examples of the comonomer to be copolymerized include a compound having a polymerizable bullet group. Preferred are the vinyl group-containing compounds shown below. In addition, copolymerization may be performed using a plurality of these comonomers.
- the polymer B contains a polymer or copolymer having a divalent group formed by removing two members selected from R 1 to R 8 in the general formula (1 ′) and having a coordination structure. is there.
- An example of this unit structure is shown below.
- Examples of the comonomer to be copolymerized include a substituted or unsubstituted divalent aromatic group having 6 to 50 nuclear carbon atoms, and a substituted or unsubstituted divalent aromatic group having 5 to 50 nuclear atoms.
- An aromatic heterocyclic group and a divalent triamine derivative having 18 to 5 carbon atoms are preferable, and copolymerization may be carried out using a plurality of comonomers. Further preferred comonomer units are shown below.
- the preferred molecular weight (Mw) of the polymer A or B is from 1000 to 300,000, and particularly preferably from 1000 to 100,000.
- the organic EL device of the present invention is an organic EL device in which one or more organic thin film layers having at least a light emitting layer are sandwiched between a cathode and an anode, wherein at least one of the organic thin film layers is It contains a coordinating metal compound or a material for an organic EL device.
- the coordinating metal compound and the material for an organic EL device of the present invention may be used for any of the above layers, but are preferably used for a light emitting layer.
- the spiro bond-containing compound of the present invention when used in a light-emitting layer, it can be usually used by mixing with various organic materials used in an organic EL device, and particularly preferably a styryl group-containing compound as dopan. Pyramine compounds Pyrylamine compounds can be used. W
- the organic EL device of the present invention is preferably manufactured on a light-transmitting substrate.
- the translucent substrate referred to here is a substrate that supports the organic EL element, and is preferably a smooth substrate having a transmittance of light of at least 50% in a visible region of 400 to 700 nm and not less than 50%.
- Specific examples include a glass plate and a polymer plate.
- the glass plate include soda-lime glass, zirconium strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, and quartz.
- the polymer plate include polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, and polysulfone.
- the anode of the organic EL device of the present invention plays a role of injecting holes into the hole transport layer or the light emitting layer, and it is effective that the anode has a work function of 4.5 eV or more.
- Specific examples of the anode material used in the present invention include indium tin oxide alloy (ITO), tin oxide (NESA), gold, silver, platinum, and copper.
- ITO indium tin oxide alloy
- NESA tin oxide
- gold silver, platinum, and copper.
- the cathode a material having a small work function is preferable for the purpose of injecting electrons into the electron transport layer or the light emitting layer.
- the anode can be produced by forming a thin film from these electrode substances by a method such as a vapor deposition method or a sputtering method.
- the transmittance of the anode with respect to the light emission be greater than 10%.
- the sheet resistance of the anode is preferably several hundreds ⁇ square or less.
- the thickness of the anode depends on the material, usually 1 0 nm ⁇ l; um, preferably:! Is selected in the range of r 0 ⁇ 2 OO nm.
- the organic EL device of the present invention preferably has a hole transport layer between the light emitting layer and the anode, and the hole transport layer preferably contains an arylamine derivative as a main component.
- the hole transporting material contained in the hole transporting layer preferably has a triplet energy of 2.5 to 3.7 eV, more preferably 2.8 to 3.7 eV. And even more preferred ,. By using a hole transport material in such a range, the excitation energy of the light emitting layer can be prevented from being deactivated.
- hole transport material those represented by the following general formulas (A) and (B) are preferable.
- a r 7 is an aromatic group having 6-4 0 carbon atoms
- a r s and A r 9 is a hydrogen atom or a carbon atoms respectively 6-4 0 aromatic group
- m is an integer of 1 to 6.
- Ar 10 and Ar 16 are aromatic groups having 6 to 40 carbon atoms, and Ar 11 to Ar 15 are each a hydrogen atom or an aromatic group having 6 to 40 carbon atoms. And the condensed numbers p, q, r, and s are each 0 or 1.
- aryl groups having 5 to 40 nuclear atoms include phenyl, naphthy ⁇ , and anthraninole. , Fenance linole, pyreninole, coloninole, bifeninole, terfeninole, pyrrolyl, furanyl, thiophenyl, benzothiophenyl, oxaziazolyl, diphenylanthra-norre, indolinole, canolebazolinole, benzolepyrinole Fluoranthenyl, acenapht fluoranthur and the like.
- Preferred arylene groups having 5 to 40 nuclear atoms include phenylene, naphthylene, anthranylene, phenanthrylene, pyrenylene, coronylene, biphenylene, terphenylene, pyrrolylene, furanylene, ⁇ ⁇ , ⁇ . ⁇ ⁇ ⁇ , ⁇ ⁇ ⁇ ⁇ ⁇ , ⁇ ⁇ ⁇ ⁇ ⁇ Examples include dolylene, pazorilene, pyridylene, benzoquinolylene, funoreolantenylene, and acenaphtofolanthenylene.
- the aromatic group having 6 to 40 carbon atoms may be further substituted with a substituent.
- Preferred examples of the substituent include an alkyl group having 1 to 6 carbon atoms (ethyl group, methyl group). , I-propyl group, n-propyl group, s-butyl group, t-butyl group, pentyl group, hexyl group, cyclopentyl group, cyclohexyl group, etc., C1-C6 alkoxy group (ethoxy) Group, methoxy group, i-propoxy group, n-propoxy group, s-butoxy group, t-butoxy group, pentoxy group, hexinoxy group, cyclopentoxy group, cyclohexoxy group, etc.), ⁇ An aryl group having 5 to 40 atoms, an amino group substituted with an aryl group having 5 to 40 nuclear atoms, an ester group having an aryl group having 5 to 40 nuclear atoms, carbon Number 1 to 6 ester group having O alkyl group, cyano group, nitro
- a hole transport material having a triplet energy force S 2.8 eV or more those represented by the following general formulas (C) to (E) are preferable.
- a r 1, A r 2 is Ri alkyl group, alkoxy group or Ariru group der good ring carbon number 6-1 8 be substituted with phenyl group of from 1 to 6 carbon, R represents It is an aryl group or an alkoxy group having 4 to 6 carbon atoms or an aryl group having 6 to 18 core carbon atoms, X is a linking group represented by a single bond, 10- or 1-S; Yes or no.
- a r 3 is ⁇ aryl group of young properly has no ring carbon atoms 6-1 8 having a substituent
- a r 4 ⁇ A r 7 is or without ring carbon atoms each having a substituent 6 to: represents an arylene group of L 8
- X 1 is a single bond, one O—, —S—, one (CH 2 ) n— (n is an integer of 1 to 6) or —C (CH 3) 2 '- indicates a linking group which is,' may even these linking groups may or may not, X 2 and X 3, their respective single bonds, one O-, one S-, -(CH 2 ) n — (n is an integer from 1 to 6) or 1 C
- (CH 3 ) 2 — represents a linking group, which may be the same or different.
- Specific examples of the groups and substituents represented by Ar 1 to A i- 7 , R, X and X 1 to X 3 in the general formulas (C) and (D) include the aforementioned Cz and Ar The same ones as mentioned in 1 to Ar 6 can be used.
- R 1 to R 12 each independently represent a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an anorecenyl group, a cyano group, an amino group, an acyl group, an alkoxycarbonyl group, a carboxy group, an alkoxy group, R 1 , R 2 , R 3 , an alkenylamino group, an aralkylamino group, a halanoalkyl group, a hydroxyl group, an aryloxy group, an aromatic hydrocarbon ring group or an aromatic heterocyclic group which may have a substituent, And R 4 , R 5 and R 6 , R 7 and R 8 , R 9 and R 10 , R 11 and R 12 respectively And adjacent substituents may form a ring.
- X represents a trivalent linking group shown below.
- Ar 1 is represented by an aromatic hydrocarbon ring group which may have a substituent, an aromatic heterocyclic group, or any of the following general formulas (F).
- R 13 to R 18 each independently represent a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an alkenyl group, a cyano group, an amino group which may have a substituent, an acyl group, Alkoxy force Nolebonyl group, carboxyl group, alkoxy group, alkylamino group, aralkylamino group, haloalkyl group, hydroxyl group, aryloxy group, aromatic hydrocarbon group which may have a substituent or aromatic heterocyclic group.
- R 13 and R 14 , R 15 and R 16 , R 17 and R 18 are each an adjacent substituent A ring may be formed together.
- the hole transport layer is as described above.
- the organic EL device of the present invention may further have a hole injection layer, and such a hole injection layer may have holes at a lower electric field intensity in the light emitting layer.
- any material can be selected from those commonly used as a hole charge transporting material and known materials used for a hole injection layer of an organic EL device.
- the hole-injecting material has the ability to transport holes, has the effect of injecting holes from the anode, has an excellent hole-injecting effect on the light-emitting layer or the light-emitting material, and is produced in the light-emitting layer.
- Compounds that prevent excitons from transferring to the electron injection layer or the electron injection material and have excellent thin film forming ability are preferable.
- phthalocyanine derivatives naphthalocyanine derivatives, borfurin conductors, oxazoles, oxazoles, triazoles, imidazoles, imidazolones, imidazole thiones, pyrazolines, pyrazolones, tetrahydromidazoles, Oxazole, oxaziazole, hydrazone, acyl hydrazone, polyarylalkane, stilbene, butadiene, benzidine-type triphenylenoleamine, styrylamine-type triphenylamine, diamin-type triphenylamine, and derivatives thereof, and polyvinyl alcohol.
- polymer materials such as polysilane, polyethylenedioxythiophene, polystyrenesulfonate, and conductive polymers, but are not limited thereto.
- the more effective hole injection materials are aromatic tertiary And a cyamine derivative of a pharmacophore.
- aromatic tertiary amine derivatives include triphenylamine, tritrilylamine, tridiphenylamine, N, N'-diphenyl-1-N, N '-(3-methylphenyl) 1-1,1' —Biphenyl 2, 4 ′ Jiamin, N, N, N ′, N ′-(4-Methylphenyl) 1, 1 ′ 1 phenyl 2, 4 ′ Jiamin, N, N, ⁇ ′, ⁇ '-(4-Methinolephenyl) — 1, 1, ⁇ biphenyl 2, 4' — Jiamin, ⁇ , ⁇ ⁇ ⁇ Jiphenyl 2 ⁇ , ⁇ 'Ginaphthyl 1, 1, ⁇ biphenyl 2, 4' Jiamin, ⁇ , ⁇ '-I (methylphenyl)
- cover B cyanine (P c) derivatives H 2 P c, C u P c, C o P c, N i P c, Z n P c, P d P c, F e P c, Mn P c, C l A l P c , C l G a P c, C l I n P c, C l S n P c, C 1 2 S i P c, (HO) A l P c, (HO) G a Pc, V ⁇ Pc, TiOPc, MoOPc, GapC- ⁇ A phthalocyanine derivative and a naphthocyanin derivative such as GaPc, but are not limited thereto. Not something.
- the hole injection / transport layer can be formed by thinning the above-mentioned compound by a known method such as a vacuum evaporation method, a spin coating method, a casting method, and an LB method.
- the thickness of the hole injection / transport layer is not particularly limited, but is usually 5 nm to 5 / m.
- the hole injecting / transporting layer may be composed of one or more of the above-mentioned materials as long as the hole transporting zone contains the compound of the present invention.
- a layer obtained by laminating a hole injection / transport layer made of a compound different from the hole injection / transport layer may be used.
- the organic semiconductor layer is a layer that assists hole injection or electron injection into the light emitting layer, Those having a conductivity of 10 to 10 S / cm or more are suitable.
- Examples of such a material for the organic semiconductor layer include thiophene-containing oligomers, conductive oligomers such as arylamine-containing oligomers disclosed in Japanese Patent Application Laid-Open No. Hei 8-19391, and impregnated oligomers. Conductive '1 "raw dendrimer, such as mindendrimer, can be used.
- the light emitting layer of the organic EL device of the present invention has the following functions.
- Injection function A function to inject holes from the anode or hole injection layer when applying an electric field, and to inject electrons from the cathode or electron injection layer.
- Transport function Function to move injected charges (electrons and holes) by electric field force
- Light-emitting function It provides a field for recombination of electrons and holes, and has a function to connect it to light emission. However, there may be a difference between the ease with which holes are injected and the ease with which electrons are injected, and the force S, which may have large or small transport abilities represented by the mobility of holes and electrons. Is preferably transferred.
- a known method such as an evaporation method, a spin coating method, and an LB method can be applied.
- a known light-emitting material (PVK, PPV, CBP, Alq, etc.) other than the light-emitting material comprising the coordinating metal compound of the present invention may be added to the light-emitting layer, if desired, as long as the object of the present invention is not impaired.
- BA lq, a known complex, etc. and a luminescent material described below.
- the compound of the present invention may be used in a state where no metal is coordinated, and the compound of the present invention may be used in a state where a metal is not coordinated and a metal is coordinated. good.
- Examples of the compound that can be contained in the light-emitting layer include a structure represented by any one of the following general formulas (L1) to (L22).
- the phenyl moiety and the thiophene moiety may be substituted by an alkyl group or an aryl group having 6 to 10 carbon atoms.
- Cz is a carbazolyl group, a C18-C60 arylarylcarbazolyl group, an azacarbazolyl group, a C18-C60 arylarylcarbazolyl group, an ataridinyl group, An enoxadininole group or a dibenzoazepinyl group, which may be substituted, wherein Ar 1 and Ar 2 are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms or substituted Or an unsubstituted heterocyclic group having 3 to 60 carbon atoms.
- examples of the light emitting material represented by the general formulas (L 1) to (L 22) include the following.
- LZ ZlO / OOZdT / lDd 8llCC0 / S00Z OAV these compounds are preferably host materials, transport charges, and have a glass transition temperature of 110 ° C. or higher.
- a triplet energy of 2.76 eV or more is preferable because it has the ability to excite green and red light emitting complexes.
- these compounds have a glass transition temperature of 110 ° C or higher and a triplet energy of 2.82 eV or more, and even 2.85 eV or more, so they can be stored at high temperatures.
- the luminous efficiency of the green light emitting device can be improved as compared with CBP.
- the triplet energy is particularly preferably from 2.82 to 2.92 eV.
- the triplet energy of the host material of the light emitting layer is 2.76 eV or more, since the ability to emit blue light is high, and that the triplet energy is 2.85 eV or more. More preferred.
- the host material of the light emitting layer has an electron transporting property.
- that the host material has an electron transporting property means that the host material is any one of the following (1) or (2).
- the electron mobility of the host material in the luminescent layer is a compound is 1 0- 6 cm 2 V s or more.
- the electron mobility can be measured by the time-of-flight method (TOF) or transient measurement of space charge limited current.
- TOF time-of-flight method
- the TOF method is described in Synthetic Metals (Synth. Met.) 111/112, (2000) p. 331.
- the transient measurement of space charge limited current is described in Electrical Transport in Solids, Pergamon Press, 1981. Pp. 346-348 can be referred to.
- the area of the light-emitting layer is divided into two, and the layer structure is (cathode / electron injection layer / cathode-side light-emitting layer / anode-side light-emitting layer Z hole transport layer Z anode side).
- the electron transporting property does not mean that there is no hole transporting property. Therefore it is an electron-transporting property, when the measured hole mobility, which may be said electron transporting at 1 0- 7 cm 2 ZV s by Redirecting a threshold.
- polycarbazole compounds such as polybutylazole and biscarbazozole which have been used as a host material of a light emitting layer generally have a hole transporting property and a small electron transporting ability.
- a hole-transporting material is used as the host material, the vicinity of the cathode-side interface of the light-emitting layer becomes a main recombination region.
- the electron injection layer contains an electron transporting material having an energy gap smaller than that of the host material forming the light emitting layer, the cathode side of the light emitting layer is reduced.
- the excited state generated around the interface is deactivated by the electron injection layer, resulting in extremely low efficiency.
- the triplet energy of the electron transport material forming the electron injection layer is smaller than the triplet energy of the host material forming the light emitting layer, the triplet energy is generated around the cathode side interface of the light emitting layer.
- the excited state is deactivated by the electron injection layer, and the efficiency becomes extremely low.
- the region where electrons and holes recombine is formed between the electron injection layer and the light-emitting layer. Away from the interface, and can prevent deactivation.
- the host material of the light emitting layer is an electron-deficient nitrogen-containing 5-membered ring derivative or a nitrogen-containing 6-membered ring derivative.
- the electron deficiency means that, for example, one or more carbon atoms in the 6 ⁇ aromatic ring are changed to nitrogen.
- the nitrogen-containing five-membered ring derivative includes imidazole, benzoimidazole, triazole, tetrazole, oxaziazole, thiadiazol, oxtriazole It is preferable that the compound has at least one kind of skeleton selected from phenyl and thiatriazole, and it is more preferable that the compound has a skeleton of imidazole or benzimidazole.
- the nitrogen-containing 6-membered ring derivative preferably has at least one skeleton selected from triazine, quinoxaline, quinoline, benzpyrimidine, pyridine, pyrazine and pyrimidine. More preferably, it has a skeleton of liadin or pyrimidine.
- C z is a substituted or unsubstituted canolebazole group or a substituted or unsubstituted azacarbazole group.
- A is an aryl-substituted nitrogen-containing ring group or a diaryl-substituted group.
- C z is a substituted or unsubstituted force / levazolyl group, or a substituted or unsubstituted azacarbazole group.
- A is an aryl-substituted nitrogen-containing ring group or a diaryl-substituted group.
- preferred nitrogen-containing rings include pyridine, quinoline, virazine, pyrimidine, quinoxaline, triazine, imidazole, imidazopyridine and the like.
- the value of the ionization potential is determined at the position of Cz, and the value is 5.6 eV to 5.8 eV.
- the organic EL device of the present invention has an electron injection / transport layer between the light emitting layer and the cathode. It is preferable that the electron injection (2) the transport layer contains a nitrogen-containing ring derivative as a main component.
- the electron transporting material used for the electron injecting and transporting layer an aromatic heterocyclic compound containing one or more heteroatoms in the molecule is preferably used, and a nitrogen-containing ring derivative is particularly preferred.
- a specific compound of the nitrogen-containing ring derivative a compound having a 5-membered azole skeleton is preferable.
- the aromatic heterocyclic compound is a compound having two or more atoms other than a carbon atom and a hydrogen atom in the basic skeleton, and may be a single ring or a condensed ring.
- the nitrogen-containing ring derivative preferably one having one or more atoms selected from nitrogen, oxygen and sulfur atoms in addition to one nitrogen atom, more preferably an aromatic having two or more nitrogen atoms in the skeleton Heterocycle.
- the heteroatom may be at the condensed position or at the non-condensed position.
- heterocyclic skeletons containing two or more heteroatoms include pyrazole, imidazole, pyrazine, pyrimidine, indazole, purine, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, and pteridine.
- compounds having a condensed azole skeleton such as imidazopyridazine, imidazopyridine, imidazopyrazine, benzimidazole, and naphtoimidazole, or compounds having a triazine skeleton. Is preferable, and condensed imidazopyridine is more preferable.
- the compound having an azole skeleton is preferably a compound represented by the general formula (J).
- R represents an aromatic group.
- X represents 0, S or N—Ra (Ra represents a hydrogen atom, an aliphatic hydrocarbon group, an aryl group or a heterocyclic group.)
- Q represents an atomic group necessary for forming a heterocyclic ring by bonding to N and X. Further, R and X, and R and Q may be bonded to form a ring when possible. / ,.)
- the aryl group includes a phenyl group, a biphenyl group, an anthranyl group, a perylenyl group, and a pyrenyl group.
- the arylene group include a phenylene group, a naphthylene group, a biphenylene group, an anthranylene group, a perylenelenylene group, and a pyrenylene group.
- the substituent include an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and a cyano group.
- This electron transfer compound is preferably a thin film-forming compound.
- electron transport material examples include the following.
- the nitrogen-containing complex is a metal complex in which a single type of nitrogen-containing ring derivative is coordinated, and the nitrogen-containing ring is a quinoline. And phenylquinidine, benzoquinoline or phenanthroline. Further, the metal complex is preferably a metal complex of quinolinol or a derivative thereof.
- these metal complexes have a small energy gap, they are excellent in injecting electrons from a cathode, have high durability against electron transport, and can provide a long-life device.
- an insulator or a semiconductor as an inorganic compound in addition to the electron transporting material as a component of the electron injection layer. If the electron injection eyebrows are made of an insulator or a semiconductor, current leakage can be effectively prevented and electron injection properties can be improved.
- Such insulators are selected from the group consisting of alkali metal chalcogenides, alkaline earth metal chalcogenides, halides of alkaline earth metals and halides of alkaline earth metal. It is preferred to use at least one metal compound. It is preferable that the electron injecting layer is refined with these metal chalcogenides or the like, since the electron injecting property can be further improved.
- the preferred alkali metal chalcogenide de, for example, L i 2 0, L i 0, N a 2 S, N a 2 S e and N a O, and the like, preferably an alkaline earth metal force
- the norecogenide include CaO, Ba ⁇ , SrO, BeO, BaS, and CaSe.
- Preferred alkali metal halides include, for example, LiF, NaF, KF, LiC1, KC1, and NaC1. Also, as the preferred alkaline earth metal halides, if Iretsue, fluorides or the like C a F 2, B a F 2, S r F 2, Mg F 2 ⁇ Pi B e F 2, fluoride Halides other than halides.
- the inorganic compound constituting the electron injection layer is preferably a microcrystalline or amorphous: K insulating thin film. If the electron injection layer is composed of these insulating thin films, a more uniform thin film is formed, so that pixel defects such as dark spots can be reduced. Examples of such inorganic compounds include alkali metal chalcogenides, alkaline earth metal chalcogenides, and alkaline metal chalcogenides. Fluoride and alkaline earth metal halide.
- a reducing dopant is added to an interface region between the cathode and the organic thin film layer.
- Examples of the reducing dopant include an alkali metal, an alkali metal complex, an alkali metal compound, an alkaline earth metal, an alkaline earth metal complex, an alkaline earth metal compound, a rare earth metal, a rare earth metal complex, and a rare earth metal. At least one kind selected from metal compounds and their halides, oxides, and the like is given.
- Li (work function: 2.93 eV), Na (work function: 2.36 eV), K (work function: 2.28 eV) , R b (work function: 2 16 eV), C s (work function: 1.95 eV) and the like, and those having a work function of 3. O eV or less are particularly preferable.
- L i, K, R b and C s are preferred.
- the alkaline earth metals include Ca (work function: 2.9 eV), Sr (work function: 2.0 to 2.5 eV), and Ba (work function: 2.52). e V), and those having a work function of 3.0 e V or less are particularly preferable.
- rare earth metal examples include Sc, Y, Ce, Tb, and Yb, and those having a work function of 3.0 eV or less are particularly preferable.
- preferred metals have a particularly high reducing ability, and the addition of a relatively small amount to the electron injection region can improve the emission luminance and extend the life of the organic EL device.
- alkaline earth metal compound examples include BaO, SrO, CaO and the like.
- B a x S r O (0 ⁇ x ⁇ 1) and, B a x C a O ( 0 immediately x rather 1), and the like, B a O, S r O , C a O is preferred.
- Examples of the rare earth metal compound Y b F 3, S c F 3, S C_ ⁇ 3, 0 3,
- the alkali metal complex, the alkaline earth metal complex, and the rare earth metal complex each include at least one of an alkali metal ion, an alkaline earth metal ion, and a rare earth metal ion as a metal ion.
- the ligands include quinolinol, benzoquinolinol, ataridinol, phenanthridine, hydroxyphenyldioxazole, hydroxyphenylthiazole, hydroxyziroxyloxazinol and hydroxydiol.
- 'Arielch ⁇ "Zazonole, Hydroxypheninolepyridin, Hydroxypheninolebenzium Mitazole, Hydroxybenzotriazole, Hydroxyfluborane, Vivilinole, Phenant Mouth Lin, Phthanolin, Ponophylline Lopentadiene, ⁇ -diketones, azomethines, and derivatives thereof are preferred, but not limited thereto.
- a reducing dopant is deposited by a resistance heating evaporation method, and at the same time, a luminescent material forming an interface region and an organic material which is an electron injection material are simultaneously deposited, and a reducing dopant is dispersed in the organic material.
- the dispersion concentration is such that the molar ratio of organic substance: reducing dopant is 100: 1 to 1: 1100, preferably 5: 1 to 1: 5.
- the reducing dopant When the reducing dopant is formed in a layer, after forming the luminescent neo-material or the electron injecting material, which is the organic layer at the interface, in a layer, the reducing dopant is independently deposited by a resistance heating deposition method. It is formed with a thickness of 0.1 to 15 nm.
- the reducing dopant When the reducing dopant is formed in the shape of an island, the light emitting material or the electron injecting material, which is the organic layer at the interface, is formed in the shape of an island, and then the reducing dopant is independently deposited by the resistance heating evaporation method. 0.05 to lnm.
- a cathode having a low work function (4 eV or less), a metal, an alloy, an electrically conductive compound, or a mixture thereof is used as the cathode.
- an electrode material include sodium, sodium-monium alloy, magnesium, lithium, magnesium-silver alloy, aluminum aluminum oxide, aluminum-lithium alloy, indium, rare metal. Earth metal and the like.
- This cathode can be manufactured by forming a thin film from these electrode substances by a method such as vapor deposition and sputtering.
- the transmittance of the cathode with respect to the emitted light be greater than 0%.
- the sheet resistance as a cathode is preferably several hundreds ⁇ / port or less, and the film thickness is usually 10 nm to: L / im, preferably 50 to 200 nm.
- an insulating thin film layer is preferably provided between the pair of electrodes.
- Examples of the material used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, and oxide. Silicon, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, oxidation Ruthenium, vanadium oxide and the like can be mentioned. Further, a mixture or a laminate thereof may be used.
- the method for forming each layer of the organic EL device of the present invention is not particularly limited.
- a conventionally known formation method such as a vacuum evaporation method and a spin coating method can be used.
- the organic thin film layer containing the compound represented by the general formula (1) or (1 ′) used in the organic EL device of the present invention was dissolved in a vacuum evaporation method, a molecular beam evaporation method (MBE method) or a solvent. It can be formed by a known method such as a solution dipping method, a spin coating method, a casting method, a percoat method, or a roll coat method.
- each organic layer of the organic EL device of the present invention is not particularly limited. In general, if the thickness of B is too thin, defects such as pinholes are likely to occur. Therefore, the range of several nm to 1 ⁇ m is usually preferable.
- the coordination metal compound of the present invention has a high solubility in an organic solvent because it has a spiro atom group / carbazolyl group. Therefore, even when the compound of the present invention has a high molecular weight and it is difficult to form a thin film by a vacuum deposition method, it can be applied to coating methods such as a divebing method, a spin coating method, a casting method, a bar coating method and a roll coating method. Thus, a thin film can be easily formed.
- the material for forming a luminescent coating film of the present invention comprises an organic solvent solution containing the coordination metal compound.
- the material for forming a luminescent coating film refers to, for example, an organic thin film layer involved in luminescence in the organic EL device of the present invention, specifically, a luminescent layer, a hole injection (transport) layer, and an electron injection (transport) layer. Is a material that is made by forming a coating film.
- solvents used when preparing the luminescent coating material include dichloromethane, dichloroethane, chloroform, carbon tetrachloride, tetrachloroethane, trichloroethane, cyclobenzene, dichlorobenzene, chlorotonolene, etc.
- Nologe Hydrocarbon solvents ether solvents such as dibutyl ether, tetrahydrofuran, dioxane anisol, methanol, ethanol, propanol, ptananol, pentanole, hexanolone, hexanolone, hexanolore, methinocellosolenolep, and ethylethyl sonoleb Solvents such as benzene, toluene, xylene, ethylbenzene, tetralamine, dodecylbenzene, hexane, octane, decane, etc .; ethyl acetate, butylacetate, amyl acetate And the like. Of these, halogenated hydrocarbon solvents, hydrocarbon solvents, and ether solvents are preferred. These solvents may be used alone or as a mixture of two or more. Note that usable solvents are not limited to these.
- the organic EL device of the present invention is preferably formed using this luminescent coating film forming material.
- the present invention will be described in more detail with reference to examples, but the present invention is not limited to these examples.
- 2-pyridylzine tough romide (13.5 g, 60.6 mmol), 1,3-jodobenzene (20 g, 60.6 mmo1), Pd (PPh 3) 4 (2.32 g, 2. Ommol) was placed in anhydrous tetrahydrofuran (300 milliliters) and stirred at room temperature for 8 hours.
- the intermediate 1-2 (4.0 g 12.9 mmo 1) and anhydrous tetrahydrofuran (100 milliliters) were placed in an argon-purged 300 milliliter flask, and — After cooling to 60 ° C, n-butyllithium 1.59 M hexane solution (12.6 milliliters) was added. After stirring the reaction solution at 120 ° C for 1 hour, it was cooled to 60 ° C, and a solution of triisopropyl borate (6.28 g, 33.4 mmo 1) in anhydrous tetrahydrofuran was added. (40 milliliters) and stirred for 1 hour. The reaction solution was gradually heated to room temperature and left overnight.
- intermediate 2-4 (1.50 g, 2.65 mmol), 4- (N-force rubazolyl) monophenylboronic acid (1.90 g, 6.62 mmo 1) Pd 2 (dba) 3 (0.12 g, 0.13 mm o 1) and cesium carbonate (5.18 g, 15.9 mm o 1) were added, and the atmosphere was replaced with argon.
- tricyclohexyl phosphine (0.10 g, 0.36 mmo 1) and dimethylformamide (20 milliliters) were added, and the mixture was heated under reflux for 8 hours.
- the reaction solution was extracted with toluene and concentrated under reduced pressure.
- the obtained solid was purified by silica gel column chromatography (elution solvent: methylene chloride) to obtain Intermediate 2-4.
- intermediate 1-1 (5 g, 17.8 mmo 1), 3,5-dibromophenylboronic acid (4.98 g, 17.8 mmo 1), Pd ( PPh 3) put 4 (1. 0 g, 0. 9 mm ol), it was replaced with argon.
- an aqueous solution 27 milliliters
- dimethoxyethane 50 milliliters
- sodium carbonate 5.66 g, 53.4 milliliters.
- the reaction solution was extracted with toluene and concentrated under reduced pressure.
- the obtained solid was purified by silica gel column chromatography (elution solvent: methylene chloride).
- intermediate 3-2 (1.65 g, 4.23 mmol), intermediate 3-1 (5.0 g, 10.6 mmo1), tris (dibenzylidene) Acetone) Dipalladium (0) (Pd (PPh 3 ) 4 ) (0.23 g, 0.2 mmo 1) was added, and the mixture was replaced with rugon.
- an aqueous solution 13 milliliters of dimethylformamide (50 milliliters) and potassium carbonate (2.49 g, 25.54 mmo1), and added. Heated to reflux for hours.
- the reaction solution was extracted with toluene and concentrated under reduced pressure.
- the obtained solid was purified by silica gel gel chromatography (elution solvent: methylene chloride) to obtain Intermediate 3-3.
- Li F as a reducing dopant was deposited, and a Li F film was formed as an electron injection layer (or a cathode).
- Metal A1 was vapor-deposited on the LiF film to form a metal cathode, thereby producing an organic EL device.
- the obtained organic EL device was subjected to a conduction test to measure a voltage, a current density, a luminous efficiency and a power efficiency. Further, the state of the luminescent surface after storage at 100 at 50 hours was observed. Table 1 shows the results.
- An organic EL device was prepared in the same manner as in Example 4, except that the compound (A7) was used instead of the compound (A17) as the light-emitting layer.
- a current test was performed to measure voltage, current density, luminous efficiency, and power efficiency, and further, the state of the luminescent surface after storage at 100 ° C. for 50 hours was observed. Table 1 shows the results.
- Example 6 In Example 4, 12 masses of the compound (A45) synthesized in Example 3 was used instead of the compound (A17) as the light emitting layer. An organic EL device was produced in the same manner as above except that a mixture obtained by adding / 0 to the following compound CBP was used.
- the obtained organic EL device was subjected to a conduction test to measure the voltage, current density, luminous efficiency, and power efficiency. Further, the state of the luminescent surface after storage at 100 ° C. for 50 hours was observed. Table 1 shows the results.
- Example 4 was repeated in the same manner as in Example 4, except that the compound (A17) was replaced by a compound obtained by adding 12% by mass of the following compound Ir (ppy) 31 to the above compound CBP as the light emitting layer.
- An organic EL device was manufactured.
- the obtained organic EL device was subjected to a conduction test to measure the voltage, current density, luminous efficiency, and power efficiency. Further, the state of the luminescent surface after storage at 100 ° C. for 50 hours was observed. Table 1 shows the results.
- the obtained organic EL device was subjected to a conduction test to measure voltage, current density, luminous efficiency, and power efficiency. Further, the state of the luminous surface after storage at 100 ° C. for 50 hours was observed. Table 1 shows the results.
- the organic EL devices of Examples 4 to 6 using the coordination metal compound of the present invention were the same as those of Comparative Examples 1 and 2 using the conventional phosphorescent compound. It operates at a lower voltage and has higher luminous efficiency and power efficiency than the device.
- the organic EL elements of Examples 4 to 6 have high-temperature heat resistance, and thus emit light uniformly for a long time.
- Lithium aluminum hydride (2.7 g, 70.5 mmo1) was suspended in anhydrous tetrahydrofuran (100 milliliters), and compound 2 (8 g, 35.2 mm) was suspended. o) A solution of anhydrous tetrahydrofuran (100 milliliters) in 1) was added dropwise at room temperature.
- i-conjugated product 6 1.5 g, 2.2 mmol
- iridium (III) acetyl acetate (Ir (acac) 3 ) (1.08 g, 2 2 mm ⁇ 1)
- glycerose 50 milliliters
- 2-phenylviridine (0.68 g, 4.4 mmo 1) was added to the reaction solution, and the mixture was heated with stirring at 250 ° C. for 10 hours.
- the film thickness was 50 nm.
- a 1,3,5—tris [2—N-phenylbenzimidazololyl] benzene film having a thickness of 50 nm was formed on this film.
- Li F as a reducing dopant was deposited to form an i F film as an electron injection layer (cathode).
- metal A1 was deposited on the iF film to form a metal cathode, and an organic EL device was manufactured.
- the luminous efficiency of the obtained organic EL device was measured under the conditions of applying a predetermined DC voltage shown in Table 1. The results are shown in Table 1.
- Compound 8 was obtained in the same manner as in the synthesis of Compound 5 except that Compound 7 (6.5 g, 1-0 mmo 1) was used instead of Compound 1 (yield: 4.1 g). , Yield: 50%).
- the complex 2 represented by the above formula was identified by 1 H-NMR and FD-MS.
- An organic EL device was prepared in the same manner as in Example 7, except that CBP in which 12% by mass of Ir (ppy) 3 was used instead of the complex 1 was used as the light-emitting layer, and the same measurement was performed. .
- the results are shown in Table 2.
- N-vinylcarbazole (0.81 g, 4.2 mmo1), compound 1'5 (01 g, 0.22 mm ⁇ 1), 2,2-azobis (isobutyronitrile) (0. 0,0.061 mmo 1) was added to butyl acetate (10 milliliters), and the mixture was heated and stirred at 80 °; for 10 hours. Acetone was added to the reaction solution to precipitate a solid, which was filtered. I had. The solid was further dissolved in methylene chloride, methanol was added to precipitate the solid, and the solid was washed with methanol to obtain Compound 16 (yield: 0.83 g).
- a reducing dopant LiF
- LiF a reducing dopant
- Metal A1 was vapor-deposited on the LiF film to form a metal cathode, thereby producing an organic EL device.
- the luminous efficiency was measured under the conditions of applying the predetermined DC voltage shown in Table 2, and the luminescence on the light emitting surface after storage at a high temperature (after 110 ° C for 50 hours) was measured. The condition was observed. The results are shown in Table 3.
- the organic EL device of Example 9 using the complex 3 as the material for an organic EL device of the present invention was driven at a lower voltage and had higher luminous efficiency than the organic EL device of Comparative Example 4, It was found that the high temperature heat resistance was high. As can be seen from Comparative Example 4, a metal compound having an ester moiety has poor heat stability, and a device using the compound generates many dark spots.
- Example 9 (II) was repeated except that complex 4 was used instead of complex 3.
- An organic EL device was manufactured by the method described above, and the luminous efficiency of the obtained organic EL device was measured under the conditions of applying a predetermined DC voltage shown in Table 4, and after high-temperature storage (110 ° C, 50 ° C). (After a time), the light emitting state of the light emitting surface was observed. The results are shown in Table 4.
- Complex 4 was synthesized as follows.
- 2,7-Dibromofluorene (3.24 g, 10 mmo 1), compound 13 (3.4 g, 10 mmo 1), toluene (15 milliliters) in an atmosphere of anoregone , dimethyl sulfoxide (1 5 ml), downy Njiruto Ryechi Ruanmoniumu chloride (0. 0 5 g, 0. 2 2 mm o 1) and 5 0 mass 0/0 hydroxide isocyanatomethyl Li um aqueous solution (4 And the mixture was stirred at 80 ° C. for 8 hours.
- the disulfide compound 17 (0.15 g, 0.3 mm o 1) and 2,5—mochifen (1.38 g, 5.7 mm o 1) were added to dimethylform.
- bis (1,5-cyclooctadiene) nickel (0) was used as a catalyst to carry out copolymerization in a conventional manner. Water was added to the reaction solution to precipitate a solid, which was washed with methanol. The obtained solid was dried under vacuum to obtain compound 18 (yield: 0.51 g).
- An organic EL device was prepared in the same manner as in Example 9 except that the complex 5 (complex-5) represented by the following formula was used instead of the complex 3, and the same measurement was performed.
- the results are shown in Table 3.
- An organic EL device was prepared in the same manner as in Example 9 except that Complex 6 represented by the following formula was used instead of Complex 3, and the same measurement was performed. The result The results are shown in Table 4.
- the organic EL device of Example 10 using the complex 4 as the material for an organic EL device of the present invention was driven at a lower voltage than the organic EL device of Comparative Example 5, and the luminous efficiency was also higher. It was found that the heat resistance was high.
- the coordinating metal compound and the material for an organic EL device of the present invention coordinate at least one ligand having a spiro bond, so that steric hindrance is large and molecules between The association is suppressed, and the organic EL device using this as a luminescent material has high luminous efficiency and high stability under high-temperature storage.
- the coordination metal compound and the material for an organic EL device of the present invention have high solubility in an organic solvent, and can be applied to a wet film forming process such as a spin coating method as a material for forming a luminescent coating film. Therefore, an organic EL device can be provided at low cost. For this reason, books The organic EL device using the coordination metal compound and the material for an organic EL device of the present invention is extremely useful as a practical organic EL device.
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Abstract
Description
Claims
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US10/569,420 US20070009760A1 (en) | 2004-08-23 | 2004-08-23 | Coordination metal compound, material for organic electroluminescence device, material for luminescent coating formation and organic electroluminescence device |
JP2005514370A JPWO2005033118A1 (ja) | 2003-08-26 | 2004-08-23 | 配位金属化合物、有機エレクトロルミネッセンス素子用材料、発光性塗膜形成用材料及び有機エレクトロルミネッセンス素子 |
EP04772383A EP1659129A4 (en) | 2003-08-26 | 2004-08-23 | COORDINATION METAL COMPOUND, MATERIAL FOR ORGANIC ELECTROLUMINESCENCE DEVICE, MATERIAL FOR LIGHT-EMITTING COATING, AND ORGANIC ELECTROLUMINESCENCE DEVICE |
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Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004113468A1 (de) * | 2003-06-26 | 2004-12-29 | Covion Organic Semiconductors Gmbh | Neue materialien für die elektrolumineszenz |
-
2004
- 2004-08-23 WO PCT/JP2004/012427 patent/WO2005033118A1/ja active Application Filing
- 2004-08-23 EP EP04772383A patent/EP1659129A4/en not_active Withdrawn
- 2004-08-23 JP JP2005514370A patent/JPWO2005033118A1/ja not_active Withdrawn
- 2004-08-23 KR KR1020067003893A patent/KR20060080922A/ko not_active Application Discontinuation
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004113468A1 (de) * | 2003-06-26 | 2004-12-29 | Covion Organic Semiconductors Gmbh | Neue materialien für die elektrolumineszenz |
Non-Patent Citations (5)
Title |
---|
BHATTACHARYA S. ET AL.: "Stereoselective oxidation of a coordinated phenoxazinylate radical with molecular oxygen", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 112, no. 11, 1990, pages 4561 - 4562, XP003018425 * |
CHEONG CHAN N.G.Y. ET AL.: "Iridium(III) hydride complexes for the catalytic enantioselective hydrogenation of imines", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 112, no. 25, 1990, pages 9400 - 9401, XP000864363 * |
JURIS A. ET AL.: "Mono- and dinuclear ruthenium(II) and osmium(II) polypiridine complexes built around spiro-bridged bis(phenanthroline) ligands: Synthesis, electrochemistry, and photophysics", INORGANIC CHEMISTRY, vol. 39, no. 16, 2000, pages 3590 - 3598, XP003018424 * |
See also references of EP1659129A4 * |
WU F. ET AL.: "Closely-spaced chelating centers: synthesis of novel spiro-bridged bis-phenanthrolines and bis-indole derivatives", TETRAHEDRON LETTERS, vol. 40, no. 41, 1999, pages 7311 - 7314, XP004178672 * |
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WO2007058227A1 (ja) * | 2005-11-18 | 2007-05-24 | Idemitsu Kosan Co., Ltd. | 芳香族アミン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
JP2007137824A (ja) * | 2005-11-18 | 2007-06-07 | Idemitsu Kosan Co Ltd | 芳香族アミン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
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JP2007281039A (ja) * | 2006-04-03 | 2007-10-25 | Seiko Epson Corp | 有機無機複合半導体材料、液状材料、有機発光素子、有機発光素子の製造方法、発光装置および電子機器 |
WO2008075517A1 (ja) * | 2006-12-18 | 2008-06-26 | Konica Minolta Holdings, Inc. | 多色燐光発光有機エレクトロルミネッセンス素子及び照明装置 |
US8299787B2 (en) | 2006-12-18 | 2012-10-30 | Konica Minolta Holdings, Inc. | Multicolor phosphorescent organic electroluminescent element and lighting system |
JPWO2008075517A1 (ja) * | 2006-12-18 | 2010-04-08 | コニカミノルタホールディングス株式会社 | 多色燐光発光有機エレクトロルミネッセンス素子及び照明装置 |
JP5532605B2 (ja) * | 2006-12-18 | 2014-06-25 | コニカミノルタ株式会社 | 多色燐光発光有機エレクトロルミネッセンス素子及び照明装置 |
WO2008120809A1 (ja) * | 2007-03-29 | 2008-10-09 | Sumitomo Chemical Company, Limited | 有機光電変換素子及びその製造に有用な重合体 |
JP2010526902A (ja) * | 2007-05-10 | 2010-08-05 | ユニバーサル ディスプレイ コーポレイション | ホスト及びドーパント機能をもつ有機金属化合物 |
JP5458890B2 (ja) * | 2007-11-08 | 2014-04-02 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
WO2009060742A1 (ja) * | 2007-11-08 | 2009-05-14 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
JP2013504884A (ja) * | 2009-09-16 | 2013-02-07 | メルク パテント ゲーエムベーハー | 電子素子製造のための調合物 |
US9666806B2 (en) | 2009-09-16 | 2017-05-30 | Merck Patent Gmbh | Formulations for the production of electronic devices |
US10714691B2 (en) | 2009-09-16 | 2020-07-14 | Merck Patent Gmbh | Formulations for the production of electronic devices |
US9882135B2 (en) | 2010-05-03 | 2018-01-30 | Merck Patent Gmbh | Formulations and electronic devices |
US10490747B2 (en) | 2010-05-03 | 2019-11-26 | Merck Patent Gmbh | Formulations and electronic devices |
JP2012224597A (ja) * | 2011-04-21 | 2012-11-15 | Konica Minolta Holdings Inc | 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、表示装置及び照明装置 |
WO2012157537A1 (ja) * | 2011-05-17 | 2012-11-22 | 東レ株式会社 | 発光素子材料および発光素子 |
JP6024455B2 (ja) * | 2011-05-17 | 2016-11-16 | 東レ株式会社 | 発光素子材料および発光素子 |
JP2015530982A (ja) * | 2012-08-07 | 2015-10-29 | メルク パテント ゲーエムベーハー | 金属錯体 |
Also Published As
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EP1659129A4 (en) | 2007-10-31 |
JPWO2005033118A1 (ja) | 2006-12-14 |
KR20060080922A (ko) | 2006-07-11 |
EP1659129A1 (en) | 2006-05-24 |
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