WO2012128298A1 - ビスカルバゾール誘導体およびこれを用いた有機エレクトロルミネッセンス素子 - Google Patents
ビスカルバゾール誘導体およびこれを用いた有機エレクトロルミネッセンス素子 Download PDFInfo
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- WO2012128298A1 WO2012128298A1 PCT/JP2012/057236 JP2012057236W WO2012128298A1 WO 2012128298 A1 WO2012128298 A1 WO 2012128298A1 JP 2012057236 W JP2012057236 W JP 2012057236W WO 2012128298 A1 WO2012128298 A1 WO 2012128298A1
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- 0 *[n]1c2ccccc2c2ccccc12 Chemical compound *[n]1c2ccccc2c2ccccc12 0.000 description 8
- SDFLTYHTFPTIGX-UHFFFAOYSA-N C[n]1c2ccccc2c2c1cccc2 Chemical compound C[n]1c2ccccc2c2c1cccc2 SDFLTYHTFPTIGX-UHFFFAOYSA-N 0.000 description 1
- JOIFBTMUBDCVMR-UHFFFAOYSA-N Cc(cc1c2ccccc22)ccc1[n]2[AlH2] Chemical compound Cc(cc1c2ccccc22)ccc1[n]2[AlH2] JOIFBTMUBDCVMR-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N c1ccccc1 Chemical compound c1ccccc1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
- H10K50/155—Hole transporting layers comprising dopants
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- 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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- 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
- H10K85/344—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising ruthenium
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- 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
- H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
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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
- H10K85/348—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising osmium
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
Definitions
- the present invention relates to a biscarbazole derivative and an organic electroluminescence device using the same.
- a biscarbazole skeleton in which two carbazoles are directly bonded by a carbon-carbon bond, and a C-carbazolyl group (1-, 2-, 3-, or 4-carbazolyl) is attached to the nitrogen atom of one carbazole skeleton. Group), an N-carbazolyl group (9-carbazolyl group), or an N-carbazolylaryl group, and an organic electroluminescence device using the same.
- Organic electroluminescence (EL) elements are promising for use as solid-state, inexpensive, large-area full-color display elements, and many developments have been made.
- an organic EL element is composed of a light emitting layer and a pair of counter electrodes sandwiching the layer. When a voltage is applied between both electrodes, electrons from the cathode side and holes from the anode side are injected into the light-emitting layer, and the injected electrons and holes recombine in the light-emitting layer, generating an excited state and being excited. When the state returns to the ground state, energy is emitted as light.
- a phosphorescent organic EL element that uses a phosphorescent organic material for the light emitting layer of the organic EL element has been proposed.
- This phosphorescent organic EL element achieves high luminous efficiency by utilizing the singlet excited state and the triplet excited state of the phosphorescent organic material.
- electrons and holes are recombined in the organic EL element, it is considered that singlet excitons and triplet excitons are generated at a ratio of 1: 3 due to the difference in spin multiplicity. If a light emitting material is used, it can be considered that the light emission efficiency is 3 to 4 times that of an element using only a fluorescent light emitting material.
- Improvement of the luminous efficiency and extension of the lifetime of organic EL elements are important issues that lead to lower power consumption and higher durability of the display, and further improvements are required.
- various studies have been made in order to improve the light emission efficiency and the device life of an organic EL device using a phosphorescent light emitting material.
- Patent Document 1 discloses a derivative having a 3,3′-biscarbazole skeleton as a phosphorescent host material.
- Patent Document 2 discloses a derivative having a 6,6′-bis (9-carbazolyl) -N, N′-disubstituted-3,3′-biscarbazole skeleton as a hole transport material.
- Patent Document 3 discloses a compound composed of a carbazole, dibenzofuran, dibenzothiophene skeleton as a phosphorescent host material, and specific examples thereof include 6,6′-bis (9-carbazolyl) -N, N′-diphenyl-3. 3,3′-biscarbazole (Compound 32) is disclosed.
- Patent Document 1 describes an application example of a 3,3′-biscarbazole derivative to a phosphorescent light-emitting layer, but does not describe application to a hole transport layer.
- Patent Document 2 discloses an application example of a derivative having a 6,6′-bis (9-carbazolyl) -N, N′-disubstituted-3,3′-biscarbazole skeleton as a hole transport material and high heat It describes the stability.
- the derivative having the skeleton has a large ionization potential, and there is a problem that the driving voltage increases when used in a hole transport layer adjacent to the light emitting layer.
- Patent Document 3 describes a derivative composed of a carbazole, dibenzofuran, and dibenzothiophene skeleton as a phosphorescent light emitting host material, but does not suggest a function as a hole transport material.
- Patent Document 4 describes a compound having a biscarbazole skeleton in which two carbazoles are directly bonded by a carbon-carbon bond (formulas (1a) and (1b)).
- a (hetero) arylamino group is bonded to the nitrogen atom of one carbazole skeleton via a 4,4'-biphenyldiyl group or a 9,9-dimethylfluorene-2,7-diyl group.
- Only compound 76 is described as a compound in which two aryl groups of the amino group are bonded via a single bond.
- Patent Document 5 describes a compound having a biscarbazole skeleton in which two carbazoles are directly bonded by a carbon-carbon bond, and a carbazolyl group bonded to a nitrogen atom of the carbazole skeleton.
- the carbazolyl group bonded to the nitrogen atom must have a heterocyclic group selected from a dibenzofuranyl group, a dibenzothiophenyl group, and a carbazolyl group.
- JP 2008-135498 A Japanese Patent Laid-Open No. 2001-220380 WO2007 / 0777810 WO2011 / 024451 gazette WO2007 / 119816
- An object of the present invention is to realize a long-life organic EL element that can be driven at a low voltage.
- the present inventors have found that a biscarbazole derivative having a specific substituent or linking group (linker) has a low ionization potential, and an organic compound containing the biscarbazole derivative. It has been found that the EL element has improved hole injection properties and can reduce the driving voltage.
- the present invention provides a biscarbazole derivative represented by the following formula (1).
- L 1 and L 2 are linking groups which may be the same or different and each independently represents a single bond or a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms.
- R 1 to R 4 may be the same or different and each independently represents a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclohexane having 3 to 20 carbon atoms.
- Alkyl group substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, substituted or unsubstituted haloalkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted
- the heteroaryl group is a pyrrolyl group, fu
- a 1 represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, wherein the heteroaryl group includes a pyrrolyl group, Furyl group, thienyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, imidazolyl group, oxazolyl group, thiazolyl group, pyrazolyl group, isoxazolyl group, isothiazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, indolyl group , Isoindolyl group, benzofuranyl group, isobenzofuranyl group,
- Ar 1 represents a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms.
- R 5 to R 8 may be the same or different and each independently represents a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cyclohexane having 3 to 20 carbon atoms.
- An alkylsilyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted carbon Represents an arylsilyl group having 6 to 30 carbon atoms, or a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms.
- Adjacent R 5 and R 6 may be bonded to each other to form a saturated or unsaturated, substituted or unsubstituted divalent group that forms part of the ring structure.
- f, g, and h each independently represent an integer of 0 to 4.
- e represents an integer of 0 to 3.
- a 2 is a group represented by the formula (2-1)
- L 2 represents a single bond
- a 2 is a group represented by the formula (2-2)
- L 2 represents a single bond.
- it represents a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms.
- the present invention further includes an anode, a cathode, and one or more organic thin film layers disposed between the anode and the cathode, and at least one of the organic thin film layers is represented by the above formula (1).
- An organic electroluminescence device comprising at least one derivative is provided.
- an organic electroluminescence element that can be driven at a low voltage and has a long lifetime.
- FIG. 1 is a schematic cross-sectional view showing an example of the organic EL element of the present invention.
- the biscarbazole derivative of the present invention is represented by the following formula (1).
- L 1 and L 2 are linking groups, which may be the same or different, and are each independently a single bond or a substituted or unsubstituted ring-forming carbon number of 6 to 30, preferably 6 to 18 Represents an arylene group.
- R 1 to R 4 may be the same or different and each independently represents a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20, preferably 1 to 10 carbon atoms, a substituted or unsubstituted carbon.
- a 1 represents a substituted or unsubstituted aryl group having 6 to 30, preferably 6 to 18 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30, preferably 6 to 18 ring atoms.
- a 2 is a group represented by the following formula (2-1) or (2-2).
- Ar 1 represents a substituted or unsubstituted aryl group having 6 to 30, preferably 6 to 18 ring carbon atoms, or a substituted or unsubstituted ring atom having 5 to 30, preferably 6 to 18 ring atoms.
- R 5 to R 8 may be the same or different and each independently represents a fluorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20, preferably 1 to 10 carbon atoms, a substituted or unsubstituted carbon.
- Adjacent R 5 and R 6 may be bonded to each other to form a saturated or unsaturated, substituted or unsubstituted divalent group that forms part of the ring structure.
- f, g, and h each independently represent an integer of 0 to 4.
- e represents an integer of 0 to 3.
- a 2 is a group represented by the formula (2-1)
- L 2 represents a single bond
- a 2 is a group represented by the formula (2-2)
- L 2 represents a single bond.
- a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms and preferably a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms.
- Examples of the arylene group represented by L 1 and L 2 include benzene, naphthalene, phenanthrene, biphenyl, terphenyl (including isomers), quarterphenyl (including isomers), fluoranthene, triphenylene, fluorene, 9,9- From dimethylfluorene, benzo [c] phenanthrene, benzo [a] triphenylene, naphth [1,2-c] phenanthrene, naphth [1,2-a] triphenylene, dibenzo [a, c] triphenylene, and benzo [b] fluoranthene And divalent residues of selected aromatic compounds, preferably 1,4-phenylene group, 1,3-phenylene group, naphthalene-2,6-diyl group, naphthalene-2,7-diyl group, It is a 9,9-dimethylfluorene-2,7-diyl group.
- alkyl groups represented by R 1 to R 4 and R 5 to R 8 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group.
- n-pentyl group n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group Group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, 1-methylpentyl group, 2-methylpentyl group, 1-pentylhexyl group, 1-butylpentyl group, 1 -Heptyloctyl group, 3-methylpentyl group and the like can be mentioned, and methyl group, t-butyl group, ethyl group, n-propyl group and isopropyl group and the
- Examples of the cycloalkyl group represented by R 1 to R 4 and R 5 to R 8 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, and the like, preferably a cyclopentyl group and a cyclohexyl group. It is.
- Examples of the alkoxy group represented by R 1 to R 4 and R 5 to R 8 include a group represented by —OY (where Y is the above alkyl group), and preferably a methoxy group, an ethoxy group, or a propoxy group. It is a group.
- haloalkyl groups represented by R 1 to R 4 and R 5 to R 8 include substitution of at least one hydrogen atom of the alkyl group with a halogen atom selected from a fluorine atom, a chlorine atom, an iodo atom, and a bromine atom. And the group obtained is preferably trifluoromethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2,2-pentafluoroethyl group, 1,1,1,3. 3,3-hexafluoro-2-propyl group.
- Examples of the haloalkoxy group represented by R 1 to R 4 and R 5 to R 8 include a group represented by —OY ′ (where Y ′ is the above haloalkyl group), preferably a trifluoromethoxy group. 2,2,2-trifluoroethoxy group, 1,1,2,2,2-pentafluoroethoxy group, 1,1,1,3,3,3-hexafluoro-2-propoxy group.
- alkylsilyl group represented by R 1 ⁇ R 4 and R 5 ⁇ R 8 is, -SiH 2 R, -SiHR 2, or -SiR 3 (wherein R is an alkyl group of said, two or three R may be the same or different, and is preferably a trimethylsilyl group, a triethylsilyl group, or a t-butyldimethylsilyl group.
- aryl groups represented by R 1 to R 4 , A 1 , Ar 1 , and R 5 to R 8 include phenyl group, naphthyl group, phenanthryl group, biphenyl group, terphenyl group, quarterphenyl group, fluoranthenyl.
- Examples of the arylsilyl group represented by R 1 to R 4 and R 5 to R 8 include —SiH 2 R ′, —SiHR ′ 2 , or —SiR ′ 3 (where R ′ is the above aryl group, and 2 Or three R's may be the same or different), and is preferably a triphenylsilyl group.
- Examples of the aralkyl group represented by R 1 to R 4 and R 5 to R 8 include a group having 7 to 30 carbon atoms obtained by substituting one hydrogen atom of the alkyl group with the aryl group, Preferably, they are a benzyl group and a naphthylmethyl group.
- the heteroaryl groups represented by R 1 to R 4 and A 1 are pyrrolyl, furyl, thienyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl , Isoxazolyl group, isothiazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, indolyl group, isoindolyl group, benzofuranyl group, isobenzofuranyl group, benzothiophenyl group, indolizinyl group, quinolidinyl group, quinolyl group, isoquinolyl group, cinnolyl group , Phthalazinyl group, quinazolinyl group, quinoxalinyl group, benzimidazolyl group, benzoxazolyl group
- the heteroaryl group represented by Ar 1 is a heteroaryl group having 5 to 30 ring atoms containing at least one heteroatom selected from a nitrogen atom, an oxygen atom, and a sulfur atom.
- Examples thereof include a pyrrolyl group, Furyl group, thienyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, imidazolyl group, oxazolyl group, thiazolyl group, pyrazolyl group, isoxazolyl group, isothiazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, indolyl group , Isoindolyl group, benzofuranyl group, isobenzofuranyl group, benzothiophenyl group, indolizinyl group, quinolidinyl group, quinolyl group, isoquino
- a butane-1,4-diyl group 1, Examples include 3-butadiene-1,4-diyl group.
- the biscarbazole derivatives represented by the formula (1) include 2,2′-biscarbazole derivatives, 3,2′-biscarbazole derivatives represented by the following formulas (3-1) to (3-4), 2, A 3′-biscarbazole derivative or a 3,3′-biscarbazole derivative is preferable, and a 3,3′-biscarbazole derivative is more preferable.
- a 1 , A 2 , L 1 , L 2 , R 1 to R 4 , and a to d are the same as above.
- the group represented by the formula (2-1) is preferably represented by the following formula (2-3) or (2-4).
- a 2 is a group represented by the formula (2-3), it is considered that the electron donating effect of A 2 works effectively and the ionization potential can be sufficiently reduced.
- a 2 is a group represented by the formula (2-4), the hole mobility is increased, so that it is considered effective for reducing the driving voltage of the organic EL element.
- the optional substituent in the case of “substituted or unsubstituted” described above and below is a fluorine atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, or an alkyl group having 1 to 20 carbon atoms.
- substituents are as described above. These substituents may be plural, and when plural, they may be the same as or different from each other.
- a 3,3′-biscarbazole derivative can be produced by the following synthesis route.
- a 1 , A 2 , L 1 , L 2 , R 1 to R 4 , and ad are the same as above.
- the organic EL device of the present invention has one or more organic thin film layers between the cathode and the anode, and at least one organic thin film layer is a light emitting layer. At least one of the organic thin film layers contains at least one biscarbazole derivative of the present invention.
- the organic EL device preferably has a hole injection layer and / or a hole transport layer, and the hole injection layer and / or the hole transport layer preferably contains at least one biscarbazole derivative of the present invention.
- the light emitting layer may contain at least one biscarbazole derivative of the present invention.
- the element configuration (4) is preferably used. (1) Anode / hole transport layer / light emitting layer / cathode (2) Anode / hole injection layer / hole transport layer / light emitting layer / cathode (3) Anode / hole injection layer / hole transport layer / light emitting layer / Electron injection layer / cathode (4) anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode Note that, between the hole transport layer and the light emitting layer, An electron barrier layer may be provided.
- a hole blocking layer may be provided as appropriate between the light emitting layer and the electron injection layer, or between the light emitting layer and the electron transport layer. According to the electron barrier layer or the hole barrier layer, electrons or holes can be confined in the light emitting layer, the recombination probability of charges in the light emitting layer can be increased, and the light emission efficiency can be improved.
- the biscarbazole derivative of the present invention is used as a material for forming a single light emitting unit type (simple type) organic EL element and a laminated light emitting unit type (tandem type) organic EL element.
- a material for forming a layer having a hole transport function provided between the light-emitting layer and the anode of these organic EL elements, and phosphorescent light-emitting that forms a light-emitting layer because triplet energy (first excited state) is large can be used as a material.
- FIG. 1 shows a schematic configuration of an example of the organic EL element of the present invention.
- the organic EL element 1 includes a transparent substrate 2, an anode 3, a cathode 4, and an organic thin film layer 10 disposed between the anode 3 and the cathode 4.
- the organic thin film layer 10 has a phosphorescent light emitting layer 5 containing a phosphorescent host material and a phosphorescent dopant.
- a hole injection / transport layer 6 or the like may be formed between the phosphorescent light emitting layer 5 and the anode 3, and an electron injection / transport layer 7 or the like may be formed between the phosphorescent light emitting layer 5 and the cathode 4.
- an electron barrier layer may be provided on the phosphorescent light emitting layer 5 on the anode 3 side, and a hole barrier layer may be provided on the phosphorescent light emitting layer 5 on the cathode 4 side.
- a host combined with a fluorescent dopant is referred to as a fluorescent host
- a host combined with a phosphorescent dopant is referred to as a phosphorescent host.
- the fluorescent host and the phosphorescent host are not distinguished only by the molecular structure. That is, the phosphorescent host means a material constituting a phosphorescent light emitting layer containing a phosphorescent dopant, and does not mean that it cannot be used as a material constituting a fluorescent light emitting layer. The same applies to the fluorescent host.
- hole injection / transport layer means “one or both of a hole injection layer and a hole transport layer”
- electron injection / transport layer means “electron injection layer and It means “one or both of the electron transport layers”.
- the organic EL element of the present invention is produced on a translucent substrate.
- the light-transmitting substrate is a substrate that supports the organic EL element, and is preferably a smooth substrate having a light transmittance in the visible region of 400 nm to 700 nm of 50% or more.
- a glass plate, a polymer plate, etc. are mentioned.
- the glass plate include those using soda lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, quartz and the like as raw materials.
- the polymer plate include those using polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, polysulfone and the like as raw materials.
- the anode of the organic EL element plays a role of injecting holes into the hole injection layer, the hole transport layer, or the light emitting layer, and it is effective to have a work function of 4.5 eV or more.
- Specific examples of the anode material include indium tin oxide alloy (ITO), tin oxide (NESA), indium zinc oxide, gold, silver, platinum, copper, and the like.
- the anode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering. When light emitted from the light emitting layer is extracted from the anode, it is preferable that the transmittance of light in the visible region of the anode is greater than 10%.
- the sheet resistance of the anode is preferably several hundred ⁇ / ⁇ or less.
- the film thickness of the anode depends on the material, but is usually selected in the range of 10 nm to 1 ⁇ m, preferably 10 nm to 200 nm.
- the cathode plays a role of injecting electrons into the electron injection layer, the electron transport layer or the light emitting layer, and is preferably formed of a material having a small work function.
- the cathode material is not particularly limited, and specifically, indium, aluminum, magnesium, magnesium-indium alloy, magnesium-aluminum alloy, aluminum-lithium alloy, aluminum-scandium-lithium alloy, magnesium-silver alloy and the like can be used.
- the cathode can be produced by forming a thin film by a method such as vapor deposition or sputtering. Moreover, you may take out light emission from the cathode side as needed.
- An organic layer having a light emitting function includes a host material and a dopant material.
- the host material mainly has a function of encouraging recombination of electrons and holes and confining excitons in the light emitting layer, and the dopant material efficiently emits excitons obtained by recombination. It has a function.
- the host material mainly has a function of confining excitons generated by the dopant in the light emitting layer.
- the ease of injecting holes into the light emitting layer may be different from the ease of injecting electrons, and the hole transport ability and electron transport ability expressed by the mobility of holes and electrons in the light emitting layer may be different. May be different.
- the light emitting layer can be formed by a known method such as a vapor deposition method, a spin coating method, or an LB method.
- the light emitting layer can also be formed by thinning a solution obtained by dissolving a binder such as a resin and a material compound in a solvent by a spin coating method or the like.
- the light emitting layer is preferably a molecular deposited film.
- the molecular deposited film is a thin film formed by deposition from a material compound in a gas phase state or a film formed by solidifying from a material compound in a solution state or a liquid phase state.
- the thin film (molecular accumulation film) formed by the LB method can be classified by the difference in the aggregation structure and the higher-order structure, and the functional difference resulting therefrom.
- the phosphorescent dopant (phosphorescent material) that forms the light emitting layer is a compound that can emit light from the triplet excited state, and is not particularly limited as long as it emits light from the triplet excited state, but Ir, Pt, Os, Au, Cu, An organometallic complex containing at least one metal selected from Re and Ru and a ligand is preferable.
- the ligand preferably has an ortho metal bond.
- a metal complex containing a metal atom selected from Ir, Os and Pt is preferred in that the phosphorescent quantum yield is high and the external quantum efficiency of the light emitting device can be further improved, and an iridium complex, an osmium complex, or a platinum complex.
- iridium complexes and platinum complexes are more preferable, and orthometalated iridium complexes are particularly preferable.
- the content of the phosphorescent dopant in the light emitting layer is not particularly limited and may be appropriately selected depending on the intended purpose. For example, it is preferably 0.1 to 70% by mass, more preferably 1 to 30% by mass. If the phosphorescent dopant content is 0.1% by mass or more, sufficient light emission can be obtained, and if it is 70% by mass or less, concentration quenching can be avoided.
- the phosphorescent host is a compound having a function of causing the phosphorescent dopant to emit light as a result of energy transfer from the excited state to the phosphorescent dopant.
- the phosphorescent host is not particularly limited as long as it is a compound capable of transferring exciton energy to the phosphorescent dopant, and can be appropriately selected according to the purpose.
- the phosphorescent host include carbazole derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, styryl.
- Anthracene derivatives fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethylidene compounds, porphyrin compounds, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thio Pyran dioxide derivatives, carbodiimide derivatives, fluorenylidene methane derivatives, distyryl pyrazine derivatives, naphthalene perylene, etc.
- metal complex polysilane compounds represented by metal complexes of a metal ring having a metal ring having a ring-shaped tetracarboxylic anhydride, a phthalocyanine derivative, an 8-quinolinol derivative, a metal phthalocyanine, a benzoxazole or a benzothiazole, poly (N- Vinyl carbazole) derivatives, aniline copolymers, thiophene oligomers, conductive polymer oligomers such as polythiophene, polymer compounds such as polythiophene derivatives, polyphenylene derivatives, polyphenylene vinylene derivatives, polyfluorene derivatives, and the like.
- a phosphorescent host may be used independently and may use 2 or more types together. Specific examples include the following compounds.
- the thickness of the light emitting layer is preferably 5 to 50 nm, more preferably 7 to 50 nm, and still more preferably 10 to 50 nm.
- the thickness is 5 nm or more, it is easy to form a light emitting layer, and when the thickness is 50 nm or less, an increase in driving voltage can be avoided.
- the organic EL device of the present invention preferably has an electron donating dopant in the interface region between the cathode and the organic thin film layer. According to such a configuration, it is possible to improve the light emission luminance and extend the life of the organic EL element.
- the electron donating dopant is selected from alkali metals, alkali metal complexes, alkali metal compounds, alkaline earth metals, alkaline earth metal complexes, alkaline earth metal compounds, rare earth metals, rare earth metal complexes, rare earth metal compounds, and the like. At least one kind.
- alkali metal examples include Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV), Cs (work function: 1.95 eV), and the like.
- a function of 2.9 eV or less is particularly preferable. Of these, K, Rb, and Cs are preferred, Rb and Cs are more preferred, and Cs is most preferred.
- alkaline earth metals include Ca (work function: 2.9 eV), Sr (work function: 2.0 eV to 2.5 eV), Ba (work function: 2.52 eV), and the like. The thing below 9 eV is especially preferable.
- rare earth metals examples include Sc, Y, Ce, Tb, Yb, and the like, and those having a work function of 2.9 eV or less are particularly preferable.
- alkali metal compound examples include alkali oxides such as Li 2 O, Cs 2 O, and K 2 O, and alkali halides such as LiF, NaF, CsF, and KF, and LiF, Li 2 O, and NaF are preferable.
- alkaline earth metal compound examples include BaO, SrO, CaO, and Ba x Sr 1-x O (0 ⁇ x ⁇ 1), Ba x Ca 1-x O (0 ⁇ x ⁇ 1) mixed with these. BaO, SrO, and CaO are preferable.
- the rare earth metal compound, YbF 3, ScF 3, ScO 3, Y 2 O 3, Ce 2 O 3, GdF 3, TbF 3 and the like, YbF 3, ScF 3, TbF 3 are preferable.
- the alkali metal complex, alkaline earth metal complex, and rare earth metal complex are not particularly limited as long as each metal ion contains at least one of an alkali metal ion, an alkaline earth metal ion, and a rare earth metal ion.
- the ligands include quinolinol, benzoquinolinol, acridinol, phenanthridinol, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiaryloxadiazole, hydroxydiarylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxybenzotriazole, Hydroxyfulborane, bipyridyl, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene, ⁇ -diketones, azomethines, and derivatives thereof are preferred, but not limited thereto.
- the electron donating dopant it is preferable to form a layered or island shape in the interface region.
- a forming method while depositing an electron donating dopant by resistance heating vapor deposition, an organic compound (light emitting material or electron injecting material) that forms an interface region is simultaneously deposited, and the electron donating dopant is dispersed in the organic compound.
- the electron donating dopant in a layered form, after forming the light emitting material or the electron injecting material which is an organic layer at the interface in a layered form, the electron donating dopant is vapor-deposited by a resistance heating vapor deposition method alone. It is formed with a thickness of 0.1 nm to 15 nm.
- the electron donating dopant is formed in an island shape, after forming the light emitting material and the electron injecting material, which are organic layers at the interface, in an island shape, the electron donating dopant is deposited by resistance heating vapor deposition alone, preferably The island is formed with a thickness of 0.05 nm to 1 nm.
- an organic layer close to the cathode may be defined as an electron injection layer.
- the electron injection layer has a function of efficiently injecting electrons from the cathode into the organic layer unit.
- an aromatic heterocyclic compound containing at least one hetero atom in the molecule is preferably used, and a nitrogen-containing ring derivative is particularly preferable.
- the nitrogen-containing ring derivative is preferably an aromatic ring having a nitrogen-containing 6-membered ring or 5-membered ring skeleton, or a condensed aromatic ring compound having a nitrogen-containing 6-membered ring or 5-membered ring skeleton.
- a nitrogen-containing ring metal chelate complex represented by the following formula (A) is preferable.
- R 2 to R 7 in formula (A) are each independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, an amino group, a hydrocarbon group having 1 to 40 carbon atoms, or an alkoxy group having 1 to 40 carbon atoms. , An aryloxy group having 6 to 50 carbon atoms, an alkoxycarbonyl group, or an aromatic heterocyclic group having 5 to 50 ring carbon atoms, which may be substituted.
- halogen atom examples include fluorine, chlorine, bromine, iodine and the like.
- Examples of the amino group which may be substituted include an alkylamino group, an arylamino group and an aralkylamino group.
- the alkylamino group and the aralkylamino group are represented as —NQ 1 Q 2 .
- Q 1 and Q 2 each independently represents an alkyl group having 1 to 20 carbon atoms or an aralkyl group having 1 to 20 carbon atoms.
- One of Q 1 and Q 2 may be a hydrogen atom or a deuterium atom.
- the arylamino group is represented as —NAr 1 Ar 2, and Ar 1 and Ar 2 each independently represent a non-condensed aromatic hydrocarbon group and a condensed aromatic hydrocarbon group having 6 to 50 carbon atoms.
- One of Ar 1 and Ar 2 may be a hydrogen atom or a deuterium atom.
- the hydrocarbon group having 1 to 40 carbon atoms includes an alkyl group, an alkenyl group, a cycloalkyl group, an aryl group, and an aralkyl group.
- the alkoxycarbonyl group is represented as —COOY ′, and Y ′ represents an alkyl group having 1 to 20 carbon atoms.
- M is aluminum (Al), gallium (Ga) or indium (In), preferably In.
- L is a group represented by the following formula (A ′) or (A ′′).
- R 8 to R 12 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted hydrocarbon group having 1 to 40 carbon atoms, and groups adjacent to each other are cyclic structures May be formed.
- R 13 to R 27 are each independently a hydrogen atom, a deuterium atom or a substituted or unsubstituted hydrocarbon group having 1 to 40 carbon atoms, and groups adjacent to each other are An annular structure may be formed.
- the hydrocarbon group having 1 to 40 carbon atoms represented by R 8 to R 12 and R 13 to R 27 in the formula (A ′) and the formula (A ′′) is represented by R 2 to R 7 in the formula (A).
- the divalent group in the case where the adjacent groups of R 8 to R 12 and R 13 to R 27 form a cyclic structure includes a tetramethylene group, a pentamethylene group, a hexamethylene group, and the like. Examples include a methylene group, diphenylmethane-2,2′-diyl group, diphenylethane-3,3′-diyl group, and diphenylpropane-4,4′-diyl group.
- 8-hydroxyquinoline or a metal complex of its derivative, an oxadiazole derivative, or a nitrogen-containing heterocyclic derivative is preferable.
- a metal chelate oxinoid compound containing a chelate of oxine generally 8-quinolinol or 8-hydroxyquinoline
- tris (8-quinolinol) aluminum is used as a specific example of the metal complex of the above 8-hydroxyquinoline or a derivative thereof.
- a metal chelate oxinoid compound containing a chelate of oxine generally 8-quinolinol or 8-hydroxyquinoline
- tris (8-quinolinol) aluminum is used.
- an oxadiazole derivative the following can be mentioned.
- Ar 17 , Ar 18 , Ar 19 , Ar 21 , Ar 22 and Ar 25 each represent a substituted or unsubstituted aromatic hydrocarbon group or condensed aromatic hydrocarbon group having 6 to 50 carbon atoms
- Ar 17 and Ar 18 , Ar 19 and Ar 21 , Ar 22 and Ar 25 may be the same or different.
- the aromatic hydrocarbon group or the condensed aromatic hydrocarbon group include a phenyl group, a naphthyl group, a biphenyl group, an anthranyl group, a perylenyl group, and a pyrenyl group.
- substituents include alkyl groups having 1 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, and cyano groups.
- Ar 20 , Ar 23, and Ar 24 each represent a substituted or unsubstituted divalent aromatic hydrocarbon group or condensed aromatic hydrocarbon group having 6 to 50 carbon atoms, and Ar 23 and Ar 24 are identical to each other. But it can be different.
- the divalent aromatic hydrocarbon group or condensed aromatic hydrocarbon group include a phenylene group, a naphthylene group, a biphenylene group, an anthranylene group, a peryleneylene group, and a pyrenylene group.
- substituents include alkyl groups having 1 to 10 carbon atoms, alkoxy groups having 1 to 10 carbon atoms, and cyano groups.
- electron transfer compounds those having good thin film forming properties are preferably used.
- Specific examples of these electron transfer compounds include the following.
- the nitrogen-containing heterocyclic derivative as the electron transfer compound is a nitrogen-containing heterocyclic derivative composed of an organic compound having the following general formula, and includes a nitrogen-containing compound that is not a metal complex. Examples thereof include a 5-membered ring or 6-membered ring containing a skeleton represented by the following formula (B) and a structure represented by the following formula (C).
- X represents a carbon atom or a nitrogen atom.
- Z 1 and Z 2 each independently represents an atomic group capable of forming a nitrogen-containing heterocycle.
- the nitrogen-containing heterocyclic derivative is more preferably an organic compound having a nitrogen-containing aromatic polycyclic group consisting of a 5-membered ring or a 6-membered ring. Further, in the case of such a nitrogen-containing aromatic polycyclic group having a plurality of nitrogen atoms, the nitrogen-containing compound having a skeleton in which the above formulas (B) and (C) or the above formula (B) and the following formula (D) are combined. Aromatic polycyclic organic compounds are preferred.
- the nitrogen-containing group of the nitrogen-containing aromatic polycyclic organic compound is selected from, for example, nitrogen-containing heterocyclic groups represented by the following general formula.
- R is an aromatic hydrocarbon group or condensed aromatic hydrocarbon group having 6 to 40 carbon atoms, an aromatic heterocyclic group or condensed aromatic heterocyclic group having 3 to 40 carbon atoms, 1 to 20 is an alkyl group or an alkoxy group having 1 to 20 carbon atoms, n is an integer of 0 to 5, and when n is an integer of 2 or more, a plurality of R may be the same or different from each other.
- preferred specific compounds include nitrogen-containing heterocyclic derivatives represented by the following formula.
- HAr-L 1 -Ar 1 -Ar 2 In the above formula, HAr is a substituted or unsubstituted nitrogen-containing heterocyclic group having 3 to 40 carbon atoms, and L 1 is a single bond, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 carbon atoms or a condensed group.
- HAr is selected from the following group, for example.
- L 1 is selected from the following group, for example.
- Ar 1 is selected from, for example, the following arylanthranyl groups.
- R 1 to R 14 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or an alkyl group having 6 to 40 carbon atoms.
- Ar 3 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 40 carbon atoms, a condensed aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group having 3 to 40 carbon atoms, or A condensed aromatic heterocyclic group.
- R 1 to R 8 may be nitrogen-containing heterocyclic derivatives each of which is a hydrogen atom or a deuterium atom.
- Ar 2 is selected from the following group, for example.
- the following compounds are also preferably used as the nitrogen-containing aromatic polycyclic organic compound as the electron transporting compound.
- R 1 to R 4 each independently represents a hydrogen atom, a deuterium atom, a substituted or unsubstituted aliphatic group having 1 to 20 carbon atoms, or a substituted or unsubstituted aliphatic group having 3 to 20 carbon atoms.
- X 1 and X 2 are each independently an oxygen atom Represents a sulfur atom or a dicyanomethylene group.
- the following compounds are also preferably used as the electron transfer compound.
- R 1 , R 2 , R 3 and R 4 are the same or different groups, and are an aromatic hydrocarbon group or a condensed aromatic hydrocarbon group represented by the following formula.
- R 5 , R 6 , R 7 , R 8 and R 9 are the same or different from each other, and are a hydrogen atom, deuterium atom, saturated or unsaturated C 1-20 alkoxyl group, saturated Alternatively, it is an unsaturated alkyl group having 1 to 20 carbon atoms, an amino group, or an alkylamino group having 1 to 20 carbon atoms. At least one of R 5 , R 6 , R 7 , R 8 and R 9 is a group other than a hydrogen atom or a deuterium atom.
- the electron transfer compound may be a polymer compound containing the nitrogen-containing heterocyclic group or the nitrogen-containing heterocyclic derivative.
- the electron transport layer of the organic EL device of the present invention particularly preferably contains at least one nitrogen-containing heterocyclic derivative represented by the following formulas (60) to (62).
- Z 1 , Z 2 and Z 3 are each independently a nitrogen atom or a carbon atom.
- R 1 and R 2 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms, substituted or unsubstituted carbon An alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms.
- n is an integer of 0 to 5, and when n is an integer of 2 or more, the plurality of R 1 may be the same or different from each other. Further, two adjacent R 1 's may be bonded to each other to form a substituted or unsubstituted hydrocarbon ring.
- Ar 1 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.
- Ar 2 is a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, substituted Alternatively, it is an unsubstituted aryl group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroaryl group having 5 to 50 ring atoms.
- Ar 1 or Ar 2 is a substituted or unsubstituted condensed aromatic hydrocarbon ring group having 10 to 50 ring carbon atoms or a substituted or unsubstituted condensed aromatic group having 9 to 50 ring atoms. It is a heterocyclic group.
- Ar 3 is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a substituted or unsubstituted heteroarylene group having 5 to 50 ring atoms.
- L 1 , L 2 and L 3 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a divalent or substituted or unsubstituted divalent atom having 9 to 50 ring atoms.
- aryl group having 6 to 50 ring carbon atoms examples include phenyl group, naphthyl group, anthryl group, phenanthryl group, naphthacenyl group, chrysenyl group, pyrenyl group, biphenyl group, terphenyl group, tolyl group, fluoranthenyl group, fluorenyl Groups and the like.
- heteroaryl group having 5 to 50 ring atoms examples include pyrrolyl group, furyl group, thienyl group, silolyl group, pyridyl group, quinolyl group, isoquinolyl group, benzofuryl group, imidazolyl group, pyrimidyl group, carbazolyl group, selenophenyl Group, oxadiazolyl group, triazolyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinoxalinyl group, acridinyl group, imidazo [1,2-a] pyridinyl group, imidazo [1,2-a] pyrimidinyl group and the like.
- Examples of the alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group.
- Examples of the haloalkyl group having 1 to 20 carbon atoms include groups obtained by substituting one or more hydrogen atoms of the alkyl group with at least one halogen atom selected from fluorine, chlorine, iodine and bromine.
- Examples of the alkoxy group having 1 to 20 carbon atoms include groups having the above alkyl group as an alkyl moiety.
- Examples of the arylene group having 6 to 50 ring carbon atoms include groups obtained by removing one hydrogen atom from the aryl group.
- Examples of the divalent condensed aromatic heterocyclic group having 9 to 50 ring atoms include groups obtained by removing one hydrogen atom from the condensed aromatic heterocyclic group described as the heteroaryl group.
- the thickness of the electron injection / transport layer is not particularly limited, but is preferably 1 nm to 100 nm.
- an insulator or a semiconductor as an inorganic compound as a constituent of the electron injection layer. If the electron injection layer is made of an insulator or a semiconductor, current leakage can be effectively prevented and the electron injection property can be improved.
- an insulator it is preferable to use at least one metal compound selected from the group consisting of alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides and alkaline earth metal halides. If the electron injection layer is composed of these alkali metal chalcogenides or the like, it is preferable in that the electron injection property can be further improved.
- preferable alkali metal chalcogenides include, for example, Li 2 O, K 2 O, Na 2 S, Na 2 Se, and Na 2 O
- preferable alkaline earth metal chalcogenides include, for example, CaO, BaO. , SrO, BeO, BaS and CaSe.
- preferable alkali metal halides include, for example, LiF, NaF, KF, LiCl, KCl, and NaCl.
- preferable alkaline earth metal halides include fluorides such as CaF 2 , BaF 2 , SrF 2 , MgF 2 and BeF 2 , and halides other than fluorides.
- the inorganic compound constituting the electron injection layer is preferably a microcrystalline or amorphous insulating thin film. If the electron injection layer is composed of these insulating thin films, a more uniform thin film is formed, and pixel defects such as dark spots can be reduced. Examples of such inorganic compounds include alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides, and alkaline earth metal halides.
- the preferred thickness of the layer is about 0.1 nm to 15 nm.
- the electron injection layer in the present invention is preferable even if it contains the above-mentioned electron donating dopant.
- an organic layer close to the anode may be defined as a hole injection layer.
- the hole injection layer has a function of efficiently injecting holes from the anode into the organic layer unit.
- the hole injection / transport layer of the present invention preferably contains a biscarbazole derivative represented by the formula (1).
- a biscarbazole derivative represented by the formula (1) As another material for forming the hole injection / transport layer, an aromatic amine compound, for example, an aromatic amine derivative represented by the following general formula (I) is preferably used.
- Ar 1 to Ar 4 represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms or a condensed aromatic hydrocarbon group, a substituted or unsubstituted ring forming atom number of 5 Represents an aromatic heterocyclic group or a condensed aromatic heterocyclic group of 50 to 50, or a group in which the aromatic hydrocarbon group or condensed aromatic hydrocarbon group and the aromatic heterocyclic group or condensed aromatic heterocyclic group are bonded. .
- L represents a substituted or unsubstituted aromatic hydrocarbon group or condensed aromatic hydrocarbon group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted ring atom number of 5 to 5 Represents 50 aromatic heterocyclic groups or condensed aromatic heterocyclic groups.
- An aromatic amine represented by the following formula (II) is also preferably used for forming the hole injection / transport layer.
- the hole transport layer of the organic EL device of the present invention may have a two-layer structure of a first hole transport layer (anode side) and a second hole transport layer (cathode side).
- the thickness of the hole injection / transport layer is not particularly limited, but is preferably 10 to 200 nm.
- a layer containing an electron accepting compound may be bonded to the positive hole transport layer or the anode side of the first hole transport layer. This is expected to reduce drive voltage and manufacturing costs.
- the electron accepting compound is preferably a compound represented by the following formula (10).
- R 7 to R 12 may be the same or different and are each independently a cyano group, —CONH 2 , carboxyl group, or —COOR 13 (R 13 is an alkyl having 1 to 20 carbon atoms) Or a cycloalkyl group having 3 to 20 carbon atoms, provided that one or more pairs of R 7 and R 8 , R 9 and R 10 , and R 11 and R 12 are combined together to form —CO—.
- a group represented by O—CO— may be represented.
- R 13 examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, a cyclopentyl group, and a cyclohexyl group.
- the thickness of the layer containing the electron-accepting compound is not particularly limited, but is preferably 5 to 20 nm.
- the extract was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated.
- the obtained solid was purified by silica gel column chromatography, and the resulting solid was washed with n-hexane and dried under reduced pressure to obtain 7.10 g of a solid.
- the following intermediate body 3 was identified by analysis of FD-MS.
- Synthesis Example 2 (Production of biscarbazole derivative (H2)) A reaction was conducted in the same manner as in Synthesis Example 1 except that 2.6 g of Intermediate 7 was used instead of Intermediate 2, and 3.2 g of white powder was obtained. The white powder was identified as the following biscarbazole derivative (H2) by FD-MS analysis.
- Synthesis Example 3 (Production of biscarbazole derivative (H3)) A reaction was conducted in the same manner as in Synthesis Example 1 except that 3.6 g of intermediate 6 was used instead of intermediate 2 to obtain 3.5 g of white powder. The white powder was identified as the following biscarbazole derivative (H3) by FD-MS analysis.
- Example 1 (Production of organic EL element) A 25 mm ⁇ 75 mm ⁇ 1.1 mm glass substrate with an ITO transparent electrode line (manufactured by Geomatic) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and further UV (Ultraviolet) ozone cleaned for 30 minutes. A glass substrate with a transparent electrode line after washing is mounted on a substrate holder of a vacuum deposition apparatus, and first the following electron-accepting compound (A) is deposited so as to cover the transparent electrode on the surface where the transparent electrode line is formed. Then, an A film having a thickness of 5 nm was formed.
- ITO transparent electrode line manufactured by Geomatic
- the following aromatic amine derivative (X1) was vapor-deposited as a 1st positive hole transport material, and the 1st positive hole transport layer with a film thickness of 157 nm was formed into a film.
- the biscarbazole derivative (H1) obtained in Synthesis Example 1 is deposited as a second hole transport material to form a second hole transport layer having a thickness of 10 nm.
- a compound (B) as a phosphorescent host and Ir (ppy) 3 as a phosphorescent dopant were co-evaporated with a thickness of 40 nm to obtain a phosphorescent light emitting layer.
- the concentration of Ir (ppy) 3 was 10% by mass.
- a compound (C) having a thickness of 20 nm, LiF having a thickness of 1 nm, and metal Al having a thickness of 80 nm were sequentially laminated on the phosphorescent light emitting layer to form a cathode. Note that LiF, which is an electron injecting electrode, was formed at a deposition rate of 1 ⁇ / min.
- the organic EL element produced as described above is caused to emit light by direct current drive, and the luminance (L) and current density are measured to obtain the current efficiency (L / J) and drive voltage (V) at a current density of 10 mA / cm 2 . It was. Further, the device lifetime at an initial luminance of 20000 cd / m 2 was determined. The results are shown in Table 1.
- Example 2 the biscarbazole derivative (H2) (Example 2) and the biscarbazole derivative (H3) (Example 3) were used in place of the biscarbazole derivative (H1) as the second hole transport material.
- an organic EL element was produced.
- the obtained organic EL device was caused to emit light by direct current driving, and the luminance (L) and current density were measured, and the current efficiency (L / J) and driving voltage (V) at a current density of 10 mA / cm 2 were obtained. Further, the device lifetime at an initial luminance of 20000 cd / m 2 was determined. The results are shown in Table 1.
- Example 1 an organic EL device was produced in the same manner as in Example 1 except that the following comparative compound 1 or comparative compound 2 was used instead of the biscarbazole derivative (H1) as the second hole transport material.
- the obtained organic EL device was caused to emit light by direct current driving, and the luminance (L) and current density were measured, and the current efficiency (L / J) and driving voltage (V) at a current density of 10 mA / cm 2 were obtained. Further, the device lifetime at an initial luminance of 20000 cd / m 2 was determined. The results are shown in Table 1.
- the biscarbazole derivative of the present invention has a long life and is useful as a material for realizing an organic EL device that can be driven at a low voltage.
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Abstract
Description
L1及びL2は連結基であり、同一でも異なっていてもよく、それぞれ独立に、単結合又は置換もしくは無置換の環形成炭素数6~30のアリーレン基を表す。
R1~R4は同一でも異なっていてもよく、それぞれ独立に、フッ素原子、シアノ基、置換もしくは無置換の炭素数1~20のアルキル基、置換もしくは無置換の炭素数3~20のシクロアルキル基、置換もしくは無置換の炭素数1~20のアルコキシ基、置換もしくは無置換の炭素数1~20のハロアルキル基、置換もしくは無置換の炭素数1~20のハロアルコキシ基、置換もしくは無置換の炭素数1~10のアルキルシリル基、置換もしくは無置換の環形成炭素数6~30のアリール基、置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、置換もしくは無置換の炭素数6~30のアリールシリル基、置換もしくは無置換の炭素数7~30のアラルキル基、又は、置換もしくは無置換の環形成原子数5~30のヘテロアリール基を表わし、該へテロアリール基は、ピロリル基、フリル基、チエニル基、ピリジル基、ピリダジニル基、ピリミジニル基、ピラジニル基、トリアジニル基、イミダゾリル基、オキサゾリル基、チアゾリル基、ピラゾリル基、イソオキサゾリル基、イソチアゾリル基、オキサジアゾリル基、チアジアゾリル基、トリアゾリル基、インドリル基、イソインドリル基、ベンゾフラニル基、イソベンゾフラニル基、ベンゾチオフェニル基、インドリジニル基、キノリジニル基、キノリル基、イソキノリル基、シンノリル基、フタラジニル基、キナゾリニル基、キノキサリニル基、ベンズイミダゾリル基、ベンズオキサゾリル基、ベンズチアゾリル基、インダゾリル基、ベンズイソキサゾリル基、ベンズイソチアゾリル基、ジベンゾフラニル基、ジベンゾチオフェニル基、フェナントリジニル基、アクリジニル基、フェナントロリニル基、フェナジニル基、フェノチアジニル基、フェノキサジニル基、及びキサンテニル基から選ばれ、隣接するR1同士、R2同士、R3同士、及びR4同士は互いに結合して、環構造の一部を形成する飽和もしくは不飽和の、置換もしくは無置換の2価の基を形成しても良い。
a、dは、それぞれ独立に、0~4の整数を表す。
b、cは、それぞれ独立に、0~3の整数を表す。
A1は、置換もしくは無置換の環形成炭素数6~30のアリール基、又は、置換もしくは無置換の環形成原子数5~30のヘテロアリール基を表し、該へテロアリール基は、ピロリル基、フリル基、チエニル基、ピリジル基、ピリダジニル基、ピリミジニル基、ピラジニル基、トリアジニル基、イミダゾリル基、オキサゾリル基、チアゾリル基、ピラゾリル基、イソオキサゾリル基、イソチアゾリル基、オキサジアゾリル基、チアジアゾリル基、トリアゾリル基、インドリル基、イソインドリル基、ベンゾフラニル基、イソベンゾフラニル基、ベンゾチオフェニル基、インドリジニル基、キノリジニル基、キノリル基、イソキノリル基、シンノリル基、フタラジニル基、キナゾリニル基、キノキサリニル基、ベンズイミダゾリル基、ベンズオキサゾリル基、ベンズチアゾリル基、インダゾリル基、ベンズイソキサゾリル基、ベンズイソチアゾリル基、ジベンゾフラニル基、ジベンゾチオフェニル基、フェナントリジニル基、アクリジニル基、フェナントロリニル基、フェナジニル基、フェノチアジニル基、フェノキサジニル基、及びキサンテニル基から選ばれる。
A2は下記式(2-1)又は(2-2)で表わされる基である。
Ar1は、置換もしくは無置換の環形成炭素数6~30のアリール基、又は、置換もしくは無置換の環形成原子数5~30のヘテロアリール基を表わす。
R5~R8は同一でも異なっていてもよく、それぞれ独立に、フッ素原子、シアノ基、置換もしくは無置換の炭素数1~20のアルキル基、置換もしくは無置換の炭素数3~20のシクロアルキル基、置換もしくは無置換の炭素数1~20のアルコキシ基、置換もしくは無置換の炭素数1~20のハロアルキル基、置換もしくは無置換の炭素数1~20のハロアルコキシ基、置換もしくは無置換の炭素数1~10のアルキルシリル基、置換もしくは無置換の環形成炭素数6~30のアリール基、置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、置換もしくは無置換の炭素数6~30のアリールシリル基、又は、置換もしくは無置換の炭素数7~30のアラルキル基を表わす。隣接するR5同士及びR6同士は互いに結合して、環構造の一部を形成する飽和もしくは不飽和の、置換もしくは無置換の2価の基を形成しても良い。
f、g、及びhは、それぞれ独立に、0~4の整数を表す。
eは0~3の整数を表す。)
ただし、A2が式(2-1)で表される基である場合、L2は単結合を表し、A2が式(2-2)で表される基である場合L2は単結合又は置換もしくは無置換の環形成炭素数6~30のアリーレン基を表す。)
本発明のビスカルバゾール誘導体は下記式(1)で表される。
R1~R4は同一でも異なっていてもよく、それぞれ独立に、フッ素原子、シアノ基、置換もしくは無置換の炭素数1~20、好ましくは1~10のアルキル基、置換もしくは無置換の炭素数3~20、好ましくは3~10のシクロアルキル基、置換もしくは無置換の炭素数1~20、好ましくは1~10のアルコキシ基、置換もしくは無置換の炭素数1~20、好ましくは1~10のハロアルキル基、置換もしくは無置換の炭素数1~20、好ましくは1~10のハロアルコキシ基、置換もしくは無置換の炭素数1~10、好ましくは1~6のアルキルシリル基、置換もしくは無置換の環形成炭素数6~30、好ましくは6~18のアリール基、置換もしくは無置換の環形成炭素数6~30、好ましくは6~18のアリールオキシ基、置換もしくは無置換の炭素数6~30、好ましくは6~18のアリールシリル基、置換もしくは無置換の炭素数7~30、好ましくは7~19のアラルキル基、又は、置換もしくは無置換の環形成原子数5~30、好ましくは6~18のヘテロアリール基を表わす。隣接するR1同士、R2同士、R3同士、及びR4同士は互いに結合して、環構造の一部を形成する飽和もしくは不飽和の、置換もしくは無置換の2価の基を形成しても良い。
a、dは、それぞれ独立に、0~4の整数を表し、b、cは、それぞれ独立に、0~3の整数を表す。
A1は、置換もしくは無置換の環形成炭素数6~30、好ましくは6~18のアリール基、又は、置換もしくは無置換の環形成原子数5~30、好ましくは6~18のヘテロアリール基を表す。
A2は下記式(2-1)又は(2-2)で表わされる基である。
R5~R8は同一でも異なっていてもよく、それぞれ独立に、フッ素原子、シアノ基、置換もしくは無置換の炭素数1~20、好ましくは1~10のアルキル基、置換もしくは無置換の炭素数3~20、好ましくは3~10のシクロアルキル基、置換もしくは無置換の炭素数1~20、好ましくは1~10のアルコキシ基、置換もしくは無置換の炭素数1~20、好ましくは1~10のハロアルキル基、置換もしくは無置換の炭素数1~20、好ましくは1~10のハロアルコキシ基、置換もしくは無置換の炭素数1~10、好ましくは1~6のアルキルシリル基、置換もしくは無置換の環形成炭素数6~30、好ましくは6~18のアリール基、置換もしくは無置換の環形成炭素数6~30、好ましくは6~18のアリールオキシ基、置換もしくは無置換の炭素数6~30、好ましくは6~18のアリールシリル基、又は、置換もしくは無置換の炭素数7~30、好ましくは7~19のアラルキル基を表わす。隣接するR5同士及びR6同士は互いに結合して、環構造の一部を形成する飽和もしくは不飽和の、置換もしくは無置換の2価の基を形成しても良い。
f、g、及びhは、それぞれ独立に、0~4の整数を表す。
eは0~3の整数を表す。
ただし、A2が式(2-1)で表される基である場合、L2は単結合を表し、A2が式(2-2)で表される基である場合L2は単結合又は置換もしくは無置換の環形成炭素数6~30のアリーレン基であり、好ましくは置換もしくは無置換の環形成炭素数6~30のアリーレン基を表す。
本発明の有機EL素子は陰極と陽極との間に、1層または2層以上の有機薄膜層を有し、少なくとも1つの有機薄膜層は発光層である。該有機薄膜層の少なくとも1層が本発明のビスカルバゾール誘導体を少なくとも1種含む。有機EL素子が正孔注入層及び/又は正孔輸送層を有し、該正孔注入層及び/又は正孔輸送層が本発明のビスカルバゾール誘導体を少なくとも1種含むことが好ましい。発光層が本発明のビスカルバゾール誘導体を少なくとも1種含んでいてもよい。
本発明の有機EL素子の代表的な素子構成としては、以下の素子構成を挙げることができるが、特にこれらに限定されるものではない。なお、(4)の素子構成が好ましく用いられる。
(1)陽極/正孔輸送層/発光層/陰極
(2)陽極/正孔注入層/正孔輸送層/発光層/陰極
(3)陽極/正孔注入層/正孔輸送層/発光層/電子注入層/陰極
(4)陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/電子注入層/陰極
なお、正孔輸送層と発光層との間には、適宜、電子障壁層を設けてもよい。また、発光層と電子注入層との間や、発光層と電子輸送層との間には、適宜、正孔障壁層を設けてもよい。電子障壁層や正孔障壁層によれば、電子又は正孔を発光層に閉じ込めて、発光層における電荷の再結合確率を高め、発光効率を向上させることができる。
本発明の有機EL素子は、透光性の基板上に作製する。透光性基板は有機EL素子を支持する基板であり、400nm~700nmの可視領域の光の透過率が50%以上で平滑な基板が好ましい。具体的には、ガラス板、ポリマー板等が挙げられる。ガラス板としては、特にソーダ石灰ガラス、バリウム・ストロンチウム含有ガラス、鉛ガラス、アルミノケイ酸ガラス、ホウケイ酸ガラス、バリウムホウケイ酸ガラス、石英等を原料として用いてなるものを挙げられる。またポリマー板としては、ポリカーボネート、アクリル、ポリエチレンテレフタレート、ポリエーテルサルファイド、ポリサルフォン等を原料として用いてなるものを挙げることができる。
有機EL素子の陽極は、正孔を正孔注入層、正孔輸送層又は発光層に注入する役割を担うものであり、4.5eV以上の仕事関数を有することが効果的である。陽極材料の具体例としては、酸化インジウム錫合金(ITO)、酸化錫(NESA)、酸化インジウム亜鉛酸化物、金、銀、白金、銅等が挙げられる。陽極はこれらの電極物質を蒸着法やスパッタリング法等の方法で薄膜を形成させることにより作製することができる。発光層からの発光を陽極から取り出す場合、陽極の可視領域の光の透過率を10%より大きくすることが好ましい。また、陽極のシート抵抗は、数百Ω/□以下が好ましい。陽極の膜厚は、材料にもよるが、通常10nm~1μm、好ましくは10nm~200nmの範囲で選択される。
陰極は電子注入層、電子輸送層又は発光層に電子を注入する役割を担うものであり、仕事関数の小さい材料により形成するのが好ましい。陰極材料は特に限定されないが、具体的にはインジウム、アルミニウム、マグネシウム、マグネシウム-インジウム合金、マグネシウム-アルミニウム合金、アルミニウム-リチウム合金、アルミニウム-スカンジウム-リチウム合金、マグネシウム-銀合金等が使用できる。陰極も、陽極と同様に、蒸着法やスパッタリング法等の方法で薄膜を形成させることにより作製することができる。また、必要に応じて、陰極側から発光を取り出してもよい。
発光機能を有する有機層であって、ドーピングシステムを採用する場合、ホスト材料とドーパント材料を含んでいる。このとき、ホスト材料は、主に電子と正孔の再結合を促し、励起子を発光層内に閉じ込める機能を有し、ドーパント材料は、再結合で得られた励起子を効率的に発光させる機能を有する。
燐光素子の場合、ホスト材料は主にドーパントで生成された励起子を発光層内に閉じ込める機能を有する。
本発明の有機EL素子は、陰極と有機薄膜層との界面領域に電子供与性ドーパントを有することも好ましい。このような構成によれば、有機EL素子における発光輝度の向上や長寿命化が図られる。電子供与性ドーパントとしては、アルカリ金属、アルカリ金属錯体、アルカリ金属化合物、アルカリ土類金属、アルカリ土類金属錯体、アルカリ土類金属化合物、希土類金属、希土類金属錯体、及び希土類金属化合物等から選ばれた少なくとも一種類が挙げられる。
本発明の有機EL素子における、主成分と電子供与性ドーパントの割合は、モル比で主成分:電子供与性ドーパント=5:1~1:5であると好ましく、2:1~1:2であるとさらに好ましい。
発光層と陰極との間に形成される有機層であって、電子を陰極から発光層へ輸送する機能を有する。電子輸送層が複数層で構成される場合、陰極に近い有機層を電子注入層と定義することがある。電子注入層は、陰極から電子を効率的に有機層ユニットに注入する機能を有する。
この含窒素環誘導体としては、例えば、下記式(A)で表される含窒素環金属キレート錯体が好ましい。
アルキルアミノ基及びアラルキルアミノ基は-NQ1Q2と表される。Q1及びQ2は、それぞれ独立に、炭素数1~20のアルキル基又は炭素数1~20のアラルキル基を表す。Q1及びQ2の一方は水素原子又は重水素原子であってもよい。
アリールアミノ基は-NAr1Ar2と表され、Ar1及びAr2は、それぞれ独立に、炭素数6~50の非縮合芳香族炭化水素基及び縮合芳香族炭化水素基を表す。Ar1及びAr2の一方は水素原子又は重水素原子であってもよい。
HAr-L1-Ar1-Ar2
前記式中、HArは、置換もしくは無置換の炭素数3~40の含窒素複素環基であり、L1は単結合、置換もしくは無置換の炭素数6~40の芳香族炭化水素基又は縮合芳香族炭化水素基又は置換もしくは無置換の炭素数3~40の芳香族複素環基又は縮合芳香族複素環基であり、Ar1は置換もしくは無置換の炭素数6~40の2価の芳香族炭化水素基であり、Ar2は置換もしくは無置換の炭素数6~40の芳香族炭化水素基又は縮合芳香族炭化水素基又は置換もしくは無置換の炭素数3~40の芳香族複素環基又は縮合芳香族複素環基である。
R1及びR2は、それぞれ独立に、置換もしくは無置換の環形成炭素数6~50のアリール基、置換もしくは無置換の環形成原子数5~50のヘテロアリール基、置換もしくは無置換の炭素数1~20のアルキル基、置換もしくは無置換の炭素数1~20のハロアルキル基又は置換もしくは無置換の炭素数1~20のアルコキシ基である。
nは、0~5の整数であり、nが2以上の整数であるとき、複数のR1は互いに同一でも異なっていてもよい。また、隣接する2つのR1同士が互いに結合して、置換もしくは無置換の炭化水素環を形成していてもよい。
Ar1は、置換もしくは無置換の環形成炭素数6~50のアリール基又は置換もしくは無置換の環形成原子数5~50のヘテロアリール基である。
Ar2は、水素原子、置換もしくは無置換の炭素数1~20のアルキル基、置換もしくは無置換の炭素数1~20のハロアルキル基、置換もしくは無置換の炭素数1~20のアルコキシ基、置換もしくは無置換の環形成炭素数6~50のアリール基又は置換もしくは無置換の環形成原子数5~50のヘテロアリール基である。
但し、Ar1、Ar2のいずれか一方は、置換もしくは無置換の環形成炭素数10~50の縮合芳香族炭化水素環基又は置換もしくは無置換の環形成原子数9~50の縮合芳香族複素環基である。
Ar3は、置換もしくは無置換の環形成炭素数6~50のアリーレン基又は置換もしくは無置換の環形成原子数5~50のヘテロアリーレン基である。
L1、L2及びL3は、それぞれ独立に、単結合、置換もしくは無置換の環形成炭素数6~50のアリーレン基、又は置換もしくは無置換の環形成原子数9~50の2価の縮合芳香族複素環基である。)
環形成原子数5~50のヘテロアリール基としては、ピローリル基、フリル基、チエニル基、シローリル基、ピリジル基、キノリル基、イソキノリル基、べンゾフリル基、イミダゾリル基、ピリミジル基、カルバゾリル基、セレノフェニル基、オキサジアゾリル基、トリアゾーリル基、ピラジニル基、ピリダジニル基、トリアジニル基、キノキサリニル基、アクリジニル基、イミダゾ[1,2-a]ピリジニル基、イミダゾ[1,2-a]ピリミジニル基などが挙げられる。
炭素数1~20のアルキル基としては、メチル基、エチル基、プロピル基、ブチル基、ペンチル基、へキシル基などが挙げられる。
炭素数1~20のハロアルキル基としては、前記アルキル基の1又は2以上の水素原子をフッ素、塩素、ヨウ素および臭素から選ばれる少なくとも1のハロゲン原子で置換して得られる基が挙げられる。
炭素数1~20のアルコキシ基としては、前記アルキル基をアルキル部位としては有する基が挙げられる。
環形成炭素数6~50のアリーレン基としては、前記アリール基から水素原子1個を除去して得られる基が挙げられる。
環形成原子数9~50の2価の縮合芳香族複素環基としては、前記ヘテロアリール基として記載した縮合芳香族複素環基から水素原子1個を除去して得られる基が挙げられる。
発光層と陽極との間に形成される有機層であって、正孔を陽極から発光層へ輸送する機能を有する。正孔輸送層が複数層で構成される場合、陽極に近い有機層を正孔注入層と定義することがある。正孔注入層は、陽極から正孔を効率的に有機層ユニットに注入する機能を有する。
また、前記一般式(I)において、Lは置換もしくは無置換の環形成炭素数6~50の芳香族炭化水素基又は縮合芳香族炭化水素基、又は置換もしくは無置換の環形成原子数5~50の芳香族複素環基又は縮合芳香族複素環基を表す。
カルバゾール15gに、エタノール70mLを加え、室温で硫酸6mL、水3mL、過ヨウ素酸2水和物8.2g、ヨウ素9.1gを加えて4時間攪拌した。反応液に水を加えて析出物をろ過し、析出物をメタノールで洗浄した。得られた固体を熱トルエンに溶かして再結晶を行った。得られた固体を減圧乾燥したところ、5.1gの白色固体を得た。FD-MSの分析により、下記中間体1と同定した。
9-フェニルカルバゾール17.7g、ヨウ化カリウム6.03g、ヨウ素酸カリウム7.78gに、硫酸5.90mL及びエタノール70mLを加え、75℃にて2時間反応した。冷却後、水、酢酸エチルを加えて分液、抽出した後、重曹水、水を用いて有機層を洗浄し、濃縮し、得られた粗生成物をシリカゲルカラムクロマトグラフィーで精製し、得られた固体を減圧乾燥したところ、21.8gの白色固体を得た。FD-MSの分析により、下記中間体2と同定した。
アルゴン雰囲気下、13.1gの中間体2に脱水トルエン、脱水エーテルを加え、-45℃に冷却し、1.58Mn-ブチルリチウムヘキサン溶液を25mL滴下して、攪拌しながら1時間かけて-5℃まで昇温した。再び-45℃まで冷却し、ボロン酸トリイソプロピルエステル25mLを徐々に滴下してから2時間反応させた。
室温に戻した後、10%希塩酸溶液を加えて攪拌し、有機層を抽出した。飽和食塩水で洗浄した後、無水硫酸マグネシウムで乾燥し、ろ別後、濃縮した。得られた固体を、シリカゲルカラムクロマトグラフィーで精製し、得られた個体をn-ヘキサンで洗浄し、減圧乾燥したところ、7.10gの固体を得た。FD-MSの分析により、下記中間体3と同定した。
アルゴン雰囲気下、2.05gの中間体1、2.0gの中間体3、テトラキス(トリフェニルフォスフィン)パラジウム0.15g、トルエン20mL、2M炭酸ナトリウム水溶液10.5mLを加えて80℃で7時間攪拌した。反応液に水を加えて固体を析出させ、固体をメタノールで洗浄した。得られた固体を熱トルエンで洗浄し、減圧乾燥したところ、2.43gの白色固体を得た。FD-MSの分析により、下記中間体4と同定した。
アルゴン雰囲気下、2-ブロモ-9,9-ジメチルフルオレン55gにヨウ素23g、過ヨウ素酸2水和物9.4g、水42mL、酢酸360mL、及び硫酸11mLを加え、65℃で30分撹拌した後、90℃で6時間反応させた。反応物を氷水に注入し、ろ過した。水で洗浄後、メタノールで洗浄することにより、61gの白色粉末を得た。FD-MSの分析により、該白色粉末を下記中間体5と同定した。
アルゴン雰囲気下、中間体5を40.0g、カルバゾール16.7g、ヨウ化銅(CuI)0.2g及び燐酸三カリウム42.4gに、trans-1,2-シクロヘキサンジアミン2mL及び1,4-ジオキサン300mLを加え、100℃にて20時間撹拌した。反応終了後、水300mLを加えた後分液し、水層を除去した。有機層を硫酸ナトリウムで乾燥させた後、濃縮した。残渣をシリカゲルカラムクロマトグラフィーで精製し、24.1gの白色結晶を得た。FD-MSの分析により、該白色結晶を下記中間体6と同定した。
合成例6において、中間体5の代わりに、4-ヨードブロモベンゼン28.2gを用いた以外は同様に反応を行ったところ、17.5gの白色個体を得た。FD-MSの分析により、下記中間体7と同定した。
アルゴン雰囲気下、3.0gの中間体2、3.0gの中間体4、Pd2(dba)30.14g、P(tBu)3HBF40.17g、t-ブトキシナトリウム1.1gに、無水キシレン30mLを加えて8時間加熱還流した。
反応液に水を加えて固体を析出させ、この固体をヘキサン、次いでメタノールで洗浄した。さらに、得られた固体をシリカゲルカラムクロマトグラフィーにて精製し、3.1gの白色結晶を得た。FD-MSの分析により、白色粉末を下記ビスカルバゾール誘導体(H1)と同定した。
合成実施例1において、中間体2の代わりに中間体7を2.6g用いた以外は同様に反応を行ったところ、3.2gの白色粉末を得た。FD-MSの分析により、白色粉末を下記ビスカルバゾール誘導体(H2)と同定した。
合成実施例1において、中間体2の代わりに中間体6を3.6g用いた以外は同様に反応を行ったところ、3.5gの白色粉末を得た。FD-MSの分析により、白色粉末を下記ビスカルバゾール誘導体(H3)と同定した。
(有機EL素子の作製)
25mm×75mm×1.1mmのITO透明電極ライン付きガラス基板(ジオマティック社製)をイソプロピルアルコール中で5分間超音波洗浄し、さらに、30分間UV(Ultraviolet)オゾン洗浄した。
洗浄後の透明電極ライン付きガラス基板を真空蒸着装置の基板ホルダーに装着し、まず透明電極ラインが形成されている面上に前記透明電極を覆うようにして下記電子受容性化合物(A)を蒸着し、膜厚5nmのA膜を成膜した。このA膜上に、第1正孔輸送材料として下記芳香族アミン誘導体(X1)を蒸着し、膜厚157nmの第1正孔輸送層を成膜した。第1正孔輸送層の成膜に続けて、第2正孔輸送材料として前記合成実施例1で得たビスカルバゾール誘導体(H1)を蒸着し、膜厚10nmの第2正孔輸送層を成膜した。
この正孔輸送層上に、燐光用ホストである化合物(B)と燐光用ドーパントであるIr(ppy)3とを厚さ40nmで共蒸着し、燐光発光層を得た。Ir(ppy)3の濃度は10質量%であった。
続いて、この燐光発光層上に、厚さ20nmの化合物(C)、厚さ1nmのLiF、厚さ80nmの金属Alを順次積層し、陰極を形成した。なお、電子注入性電極であるLiFは、1Å/minの成膜速度で形成した。
以上のように作製した有機EL素子を直流電流駆動により発光させ、輝度(L)、電流密度を測定し、電流密度10mA/cm2における電流効率(L/J)、駆動電圧(V)を求めた。さらに初期輝度20000cd/m2における素子寿命を求めた。結果を表1に示す。
実施例1において、第2正孔輸送材料としてビスカルバゾール誘導体(H1)の代わりに、ビスカルバゾール誘導体(H2)(実施例2)、ビスカルバゾール誘導体(H3)(実施例3)を用いた以外は、実施例1と同様にして有機EL素子を作製した。得られた有機EL素子を直流電流駆動により発光させ、輝度(L)、電流密度を測定し、電流密度10mA/cm2における電流効率(L/J)、駆動電圧(V)を求めた。さらに初期輝度20000cd/m2における素子寿命を求めた。結果を表1に示す。
実施例1において、第2正孔輸送材料としてビスカルバゾール誘導体(H1)の代わりに、下記比較化合物1又は比較化合物2を用いた以外は、実施例1と同様にして有機EL素子を作製した。得られた有機EL素子を直流電流駆動により発光させ、輝度(L)、電流密度を測定し、電流密度10mA/cm2における電流効率(L/J)、駆動電圧(V)を求めた。さらに初期輝度20000cd/m2における素子寿命を求めた。結果を表1に示す。
Claims (18)
- 下記式(1)で表されるビスカルバゾール誘導体。
L1及びL2は連結基であり、同一でも異なっていてもよく、それぞれ独立に、単結合又は置換もしくは無置換の環形成炭素数6~30のアリーレン基を表す。
R1~R4は同一でも異なっていてもよく、それぞれ独立に、フッ素原子、シアノ基、置換もしくは無置換の炭素数1~20のアルキル基、置換もしくは無置換の炭素数3~20のシクロアルキル基、置換もしくは無置換の炭素数1~20のアルコキシ基、置換もしくは無置換の炭素数1~20のハロアルキル基、置換もしくは無置換の炭素数1~20のハロアルコキシ基、置換もしくは無置換の炭素数1~10のアルキルシリル基、置換もしくは無置換の環形成炭素数6~30のアリール基、置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、置換もしくは無置換の炭素数6~30のアリールシリル基、置換もしくは無置換の炭素数7~30のアラルキル基、又は、置換もしくは無置換の環形成原子数5~30のアリール基を表わし、該へテロアリール基は、ピロリル基、フリル基、チエニル基、ピリジル基、ピリダジニル基、ピリミジニル基、ピラジニル基、トリアジニル基、イミダゾリル基、オキサゾリル基、チアゾリル基、ピラゾリル基、イソオキサゾリル基、イソチアゾリル基、オキサジアゾリル基、チアジアゾリル基、トリアゾリル基、インドリル基、イソインドリル基、ベンゾフラニル基、イソベンゾフラニル基、ベンゾチオフェニル基、インドリジニル基、キノリジニル基、キノリル基、イソキノリル基、シンノリル基、フタラジニル基、キナゾリニル基、キノキサリニル基、ベンズイミダゾリル基、ベンズオキサゾリル基、ベンズチアゾリル基、インダゾリル基、ベンズイソキサゾリル基、ベンズイソチアゾリル基、ジベンゾフラニル基、ジベンゾチオフェニル基、フェナントリジニル基、アクリジニル基、フェナントロリニル基、フェナジニル基、フェノチアジニル基、フェノキサジニル基、及びキサンテニル基から選ばれ、隣接するR1同士、R2同士、R3同士、及びR4同士は互いに結合して、環構造の一部を形成する飽和もしくは不飽和の、置換もしくは無置換の2価の基を形成しても良い。
a、dは、それぞれ独立に、0~4の整数を表す。
b、cは、それぞれ独立に、0~3の整数を表す。
A1は、置換もしくは無置換の環形成炭素数6~30のアリール基、又は、置換もしくは無置換の環形成原子数5~30のヘテロアリール基を表し、該へテロアリール基は、ピロリル基、フリル基、チエニル基、ピリジル基、ピリダジニル基、ピリミジニル基、ピラジニル基、トリアジニル基、イミダゾリル基、オキサゾリル基、チアゾリル基、ピラゾリル基、イソオキサゾリル基、イソチアゾリル基、オキサジアゾリル基、チアジアゾリル基、トリアゾリル基、インドリル基、イソインドリル基、ベンゾフラニル基、イソベンゾフラニル基、ベンゾチオフェニル基、インドリジニル基、キノリジニル基、キノリル基、イソキノリル基、シンノリル基、フタラジニル基、キナゾリニル基、キノキサリニル基、ベンズイミダゾリル基、ベンズオキサゾリル基、ベンズチアゾリル基、インダゾリル基、ベンズイソキサゾリル基、ベンズイソチアゾリル基、ジベンゾフラニル基、ジベンゾチオフェニル基、フェナントリジニル基、アクリジニル基、フェナントロリニル基、フェナジニル基、フェノチアジニル基、フェノキサジニル基、及びキサンテニル基から選ばれる。
A2は下記式(2-1)又は(2-2)で表わされる基である。
Ar1は、置換もしくは無置換の環形成炭素数6~30のアリール基、又は、置換もしくは無置換の環形成原子数5~30のヘテロアリール基を表わす。
R5~R8は同一でも異なっていてもよく、それぞれ独立に、フッ素原子、シアノ基、置換もしくは無置換の炭素数1~20のアルキル基、置換もしくは無置換の炭素数3~20のシクロアルキル基、置換もしくは無置換の炭素数1~20のアルコキシ基、置換もしくは無置換の炭素数1~20のハロアルキル基、置換もしくは無置換の炭素数1~20のハロアルコキシ基、置換もしくは無置換の炭素数1~10のアルキルシリル基、置換もしくは無置換の環形成炭素数6~30のアリール基、置換もしくは無置換の環形成炭素数6~30のアリールオキシ基、置換もしくは無置換の炭素数6~30のアリールシリル基、又は、置換もしくは無置換の炭素数7~30のアラルキル基を表わし、隣接するR5同士及びR6同士は互いに結合して、環構造の一部を形成する飽和もしくは不飽和の、置換もしくは無置換の2価の基を形成しても良い。
f、g、及びhは、それぞれ独立に、0~4の整数を表す。
eは0~3の整数を表す。)
ただし、A2が式(2-1)で表される基である場合、L2は単結合を表し、A2が式(2-2)で表される基である場合L2は単結合又は置換もしくは無置換の環形成炭素数6~30のアリーレン基を表す。) - 前記L2が表す環形成炭素数6~30のアリーレン基がベンゼン、ビフェニル、ナフタレン、フェナントレン、フルオレン、又は9,9-ジメチルフルオレンから選ばれる芳香族化合物の2価の残基である請求項1~4のいずれか1項に記載のビスカルバゾール誘導体。
- 前記L2が置換もしくは無置換の1,4-フェニレン基である請求項1~5のいずれか1項に記載のビスカルバゾール誘導体。
- 前記L2が置換もしくは無置換の1,3-フェニレン基である請求項1~5のいずれか1項に記載のビスカルバゾール誘導体。
- 前記L2が置換もしくは無置換の9,9-ジメチルフルオレン-2,7-ジイル基である請求項1~5のいずれか1項に記載のビスカルバゾール誘導体。
- 前記R1~R4及びA1が表す環形成原子数5~30のヘテロアリール基がフリル基、チエニル基、ベンゾフラニル基、ベンゾチオフェニル基、ジベンゾフラニル基、及びジベンゾチオフェニル基から選ばれる請求項1~8のいずれか1項に記載のビスカルバゾール誘導体。
- 請求項1~9のいずれか1項に記載のビスカルバゾール誘導体を少なくとも1種含有する有機エレクトロルミネッセンス素子用材料。
- 請求項1~9のいずれか1項に記載のビスカルバゾール誘導体を少なくとも1種含有する正孔輸送材料。
- 陽極、陰極、及び該陽極と陰極の間に配置された1層以上の有機薄膜層を含み、該有機薄膜層の少なくとも1層が請求項1~9のいずれか1項に記載のビスカルバゾール誘導体を少なくとも1種含む有機エレクトロルミネッセンス素子。
- 前記有機薄膜層が正孔輸送層及び/又は正孔注入層を有し、前記正孔輸送層及び/又は正孔注入層が前記ビスカルバゾール誘導体を少なくとも1種含む請求項12に記載の有機エレクトロルミネッセンス素子。
- 前記有機薄膜層が発光層を有し、前記発光層が燐光発光性材料を含有する請求項12~14のいずれか1項に記載の有機エレクトロルミネッセンス素子。
- 前記燐光発光性材料がイリジウム(Ir),オスミウム(Os)及び白金(Pt)から選ばれる金属のオルトメタル化錯体である請求項15記載の有機エレクトロルミネッセンス素子。
- 前記有機薄膜層が発光層を有し、前記発光層が蛍光発光性材料を含有する請求項12~14のいずれか1項に記載の有機エレクトロルミネッセンス素子。
- 前記有機薄膜層が電子輸送層を有し、前記電子輸送層が下記式(60)~(62)のいずれかで表される含窒素複素環誘導体を含有している請求項12~17のいずれか1項に記載の有機エレクトロルミネッセンス素子。
R1及びR2は、それぞれ独立に、置換もしくは無置換の環形成炭素数6~50のアリール基、置換もしくは無置換の環形成原子数5~50のヘテロアリール基、炭素数1~20のアルキル基、置換もしくは無置換の炭素数1~20のハロアルキル基又は置換もしくは無置換の炭素数1~20のアルコキシ基である。
nは、0~5の整数であり、nが2以上の整数であるとき、複数のR1は互いに同一でも異なっていてもよい。また、隣接する2つのR1同士が互いに結合して、置換もしくは無置換の炭化水素環を形成していてもよい。
Ar1は、置換もしくは無置換の環形成炭素数6~50のアリール基又は置換もしくは無置換の環形成原子数5~50のヘテロアリール基である。
Ar2は、水素原子、置換もしくは無置換の炭素数1~20のアルキル基、置換もしくは無置換の炭素数1~20のハロアルキル基、置換もしくは無置換の炭素数1~20のアルコキシ基、置換もしくは無置換の環形成炭素数6~50のアリール基又は置換もしくは無置換の環形成原子数5~50のヘテロアリール基である。
但し、Ar1、Ar2のいずれか一方は、置換もしくは無置換の環形成炭素数10~50の縮合芳香族炭化水素環基又は置換もしくは無置換の環形成原子数9~50の縮合芳香族複素環基である。
Ar3は、置換もしくは無置換の環形成炭素数6~50のアリーレン基又は置換もしくは無置換の環形成原子数5~50のヘテロアリーレン基である。
L1、L2及びL3は、それぞれ独立に、単結合、置換もしくは無置換の環形成炭素数6~50のアリーレン基、又は置換もしくは無置換の環形成原子数9~50の2価の縮合芳香族複素環基である。)
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EP12759920.7A EP2690093A4 (en) | 2011-03-24 | 2012-03-21 | BISCARBAZOLE DERIVATIVE AND ORGANIC ELECTROLUMINESCENT ELEMENT THEREWITH |
JP2013505994A JPWO2012128298A1 (ja) | 2011-03-24 | 2012-03-21 | ビスカルバゾール誘導体およびこれを用いた有機エレクトロルミネッセンス素子 |
KR1020137024891A KR20140009393A (ko) | 2011-03-24 | 2012-03-21 | 비스카바졸 유도체 및 이것을 이용한 유기 전기발광 소자 |
CN2012800148690A CN103429570A (zh) | 2011-03-24 | 2012-03-21 | 双咔唑衍生物及使用其的有机电致发光元件 |
US14/006,514 US9564595B2 (en) | 2011-03-24 | 2012-03-21 | Bis-carbazole derivative and organic electroluminescent element using same |
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CN115368293A (zh) * | 2021-05-18 | 2022-11-22 | 三星Sdi株式会社 | 用于有机光电装置的化合物、用于有机光电装置的组合物、有机光电装置及显示装置 |
Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001220380A (ja) | 2000-02-08 | 2001-08-14 | Samsung Sdi Co Ltd | 高い熱安定性を持つ有機電界発光素子用正孔輸送性化合物及びその製造方法並びに有機電界発光素子 |
WO2007077810A1 (ja) | 2006-01-05 | 2007-07-12 | 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 |
WO2007119816A1 (ja) | 2006-04-19 | 2007-10-25 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子材料、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 |
WO2007132886A1 (ja) * | 2006-05-17 | 2007-11-22 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子材料、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 |
WO2007132678A1 (ja) * | 2006-05-11 | 2007-11-22 | Idemitsu Kosan Co., Ltd. | 有機エレクトロルミネッセンス素子 |
JP2008135498A (ja) | 2006-11-28 | 2008-06-12 | Toray Ind Inc | 発光素子 |
JP2010135467A (ja) * | 2008-12-03 | 2010-06-17 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、該素子を備えた照明装置及び表示装置 |
WO2011024451A1 (ja) | 2009-08-28 | 2011-03-03 | 保土谷化学工業株式会社 | カルバゾール環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 |
JP2011054931A (ja) * | 2009-08-05 | 2011-03-17 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、及びその製造方法 |
WO2011055934A2 (ko) * | 2009-11-03 | 2011-05-12 | 제일모직 주식회사 | 유기광전소자용 화합물 및 이를 포함하는 유기광전소자 |
KR20110066766A (ko) * | 2009-12-11 | 2011-06-17 | 덕산하이메탈(주) | 오원자 헤테로 고리를 포함하는 화합물 및 이를 이용한 유기전기소자, 그 단말 |
WO2011125680A1 (ja) * | 2010-03-31 | 2011-10-13 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 |
WO2011139055A2 (ko) * | 2010-05-03 | 2011-11-10 | 제일모직 주식회사 | 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치 |
Family Cites Families (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3139321B2 (ja) | 1994-03-31 | 2001-02-26 | 東レ株式会社 | 発光素子 |
US7560175B2 (en) * | 1999-12-31 | 2009-07-14 | Lg Chem, Ltd. | Electroluminescent devices with low work function anode |
JP2007039406A (ja) * | 2005-08-05 | 2007-02-15 | Idemitsu Kosan Co Ltd | 含窒素複素環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 |
JP2009114369A (ja) * | 2007-11-08 | 2009-05-28 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス材料、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 |
JP5593696B2 (ja) * | 2007-11-08 | 2014-09-24 | 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の製造方法 |
JP5381719B2 (ja) | 2008-02-20 | 2014-01-08 | コニカミノルタ株式会社 | 白色発光有機エレクトロルミネッセンス素子 |
WO2011016216A1 (ja) | 2009-08-04 | 2011-02-10 | パナソニック株式会社 | 発光素子駆動装置及び携帯機器 |
JP5423255B2 (ja) | 2009-09-01 | 2014-02-19 | 住友電装株式会社 | 電線交換機能付き電線調尺装置 |
US9306174B2 (en) | 2009-10-23 | 2016-04-05 | Hodogaya Chemical Co., Ltd. | Organic electroluminescent device |
CN102598343B (zh) | 2009-10-23 | 2015-07-08 | 保土谷化学工业株式会社 | 有机电致发光器件 |
US8828561B2 (en) * | 2009-11-03 | 2014-09-09 | Cheil Industries, Inc. | Compound for organic photoelectric device and organic photoelectric device including the same |
KR101783344B1 (ko) * | 2009-12-28 | 2017-09-29 | 신닛테츠 수미킨 가가쿠 가부시키가이샤 | 유기 전계 발광 소자 |
KR20120057561A (ko) | 2010-04-20 | 2012-06-05 | 이데미쓰 고산 가부시키가이샤 | 비스카르바졸 유도체, 유기 일렉트로루미네선스 소자용 재료 및 그것을 사용한 유기 일렉트로루미네선스 소자 |
JP2013201153A (ja) * | 2010-06-08 | 2013-10-03 | Idemitsu Kosan Co Ltd | 有機エレクトロルミネッセンス素子 |
JP2013200939A (ja) * | 2010-06-08 | 2013-10-03 | Idemitsu Kosan Co Ltd | 有機エレクトロルミネッセンス素子 |
CN102884156B (zh) * | 2010-06-24 | 2016-01-20 | 东丽株式会社 | 发光元件材料和发光元件 |
KR101477614B1 (ko) * | 2010-09-17 | 2014-12-31 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자 |
JPWO2012090806A1 (ja) | 2010-12-27 | 2014-06-05 | 東レ株式会社 | 発光素子材料および発光素子 |
WO2012108881A1 (en) | 2011-02-11 | 2012-08-16 | Universal Display Corporation | Organic light emitting device and materials for use in same |
JP5747555B2 (ja) | 2011-02-24 | 2015-07-15 | 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 |
KR101427611B1 (ko) * | 2011-03-08 | 2014-08-11 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자 |
EP2688120B1 (en) | 2011-03-14 | 2017-08-23 | Toray Industries, Inc. | Light-emitting element material and light-emitting element |
-
2012
- 2012-03-21 CN CN2012800148690A patent/CN103429570A/zh active Pending
- 2012-03-21 US US14/006,514 patent/US9564595B2/en active Active
- 2012-03-21 WO PCT/JP2012/057236 patent/WO2012128298A1/ja active Application Filing
- 2012-03-21 EP EP12759920.7A patent/EP2690093A4/en not_active Withdrawn
- 2012-03-21 JP JP2013505994A patent/JPWO2012128298A1/ja active Pending
- 2012-03-21 KR KR1020137024891A patent/KR20140009393A/ko not_active Application Discontinuation
- 2012-03-23 TW TW101110230A patent/TW201245407A/zh unknown
Patent Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2001220380A (ja) | 2000-02-08 | 2001-08-14 | Samsung Sdi Co Ltd | 高い熱安定性を持つ有機電界発光素子用正孔輸送性化合物及びその製造方法並びに有機電界発光素子 |
WO2007077810A1 (ja) | 2006-01-05 | 2007-07-12 | 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 |
WO2007119816A1 (ja) | 2006-04-19 | 2007-10-25 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子材料、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 |
WO2007132678A1 (ja) * | 2006-05-11 | 2007-11-22 | Idemitsu Kosan Co., Ltd. | 有機エレクトロルミネッセンス素子 |
WO2007132886A1 (ja) * | 2006-05-17 | 2007-11-22 | Konica Minolta Holdings, Inc. | 有機エレクトロルミネッセンス素子材料、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 |
JP2008135498A (ja) | 2006-11-28 | 2008-06-12 | Toray Ind Inc | 発光素子 |
JP2010135467A (ja) * | 2008-12-03 | 2010-06-17 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、該素子を備えた照明装置及び表示装置 |
JP2011054931A (ja) * | 2009-08-05 | 2011-03-17 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、及びその製造方法 |
WO2011024451A1 (ja) | 2009-08-28 | 2011-03-03 | 保土谷化学工業株式会社 | カルバゾール環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 |
WO2011055934A2 (ko) * | 2009-11-03 | 2011-05-12 | 제일모직 주식회사 | 유기광전소자용 화합물 및 이를 포함하는 유기광전소자 |
KR20110066766A (ko) * | 2009-12-11 | 2011-06-17 | 덕산하이메탈(주) | 오원자 헤테로 고리를 포함하는 화합물 및 이를 이용한 유기전기소자, 그 단말 |
WO2011125680A1 (ja) * | 2010-03-31 | 2011-10-13 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子用材料及びそれを用いた有機エレクトロルミネッセンス素子 |
WO2011139055A2 (ko) * | 2010-05-03 | 2011-11-10 | 제일모직 주식회사 | 유기광전자소자용 화합물, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치 |
Non-Patent Citations (1)
Title |
---|
See also references of EP2690093A4 |
Cited By (112)
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Also Published As
Publication number | Publication date |
---|---|
JPWO2012128298A1 (ja) | 2014-07-24 |
TW201245407A (en) | 2012-11-16 |
US20140008633A1 (en) | 2014-01-09 |
KR20140009393A (ko) | 2014-01-22 |
EP2690093A1 (en) | 2014-01-29 |
CN103429570A (zh) | 2013-12-04 |
US9564595B2 (en) | 2017-02-07 |
EP2690093A4 (en) | 2014-08-13 |
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