WO2013150909A1 - Élément électroluminescent organique - Google Patents

Élément électroluminescent organique Download PDF

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WO2013150909A1
WO2013150909A1 PCT/JP2013/058659 JP2013058659W WO2013150909A1 WO 2013150909 A1 WO2013150909 A1 WO 2013150909A1 JP 2013058659 W JP2013058659 W JP 2013058659W WO 2013150909 A1 WO2013150909 A1 WO 2013150909A1
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light emitting
dopant
emitting layer
ring
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みゆき 岡庭
檜山　邦雅
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コニカミノルタ株式会社
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Priority to JP2014509107A priority Critical patent/JP6024744B2/ja
Priority to KR1020147027329A priority patent/KR101708988B1/ko
Publication of WO2013150909A1 publication Critical patent/WO2013150909A1/fr

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Definitions

  • the present invention relates to an organic electroluminescence element.
  • ELD electroluminescence display
  • inorganic EL elements inorganic electroluminescence elements
  • organic electroluminescence elements organic EL elements
  • Inorganic EL elements have been used as planar light sources, but an alternating high voltage is required to drive the light emitting elements.
  • an organic EL device has a structure in which a light emitting layer containing a compound that emits light is sandwiched between a cathode and an anode, and injects electrons and holes into the light emitting layer to recombine them, thereby excitons.
  • This is an element that emits light by utilizing light emission (fluorescence / phosphorescence) when the exciton is deactivated. It can emit light at a voltage of several volts to several tens of volts, and is self-luminous, so it has a wide viewing angle, high visibility, and it is a thin-film, completely solid element that saves space and portability. It is attracting attention from the viewpoint.
  • Non-Patent Document 1 As the development of organic EL elements for practical use, since Princeton University has reported organic EL elements using phosphorescence emission from excited triplets (see, for example, Non-Patent Document 1), phosphorous at room temperature. Research on materials that exhibit light has become active (see, for example, Non-Patent Document 2 and Patent Document 1). In addition, recently discovered organic EL devices that use phosphorescence can realize a luminous efficiency that is approximately four times that of previous devices that use fluorescence. Research and development of light-emitting element layer configurations and electrodes are performed all over the world. For example, many compounds have been studied for synthesis centering on dopants of heavy metal complexes such as iridium complexes (see, for example, Non-Patent Document 3).
  • the dopant concentration is too high, for example, when a tris body having the same ligand structure is used as the dopant, the dopants are easily stacked and concentration quenching occurs.
  • concentration quenching occurs as a means for increasing the concentration of the blue dopant, for example, it is conceivable to use a hetero-body having a different ligand instead of a tris-body as a dopant of an iridium complex-based heavy metal complex. As a result, stacking of dopants is suppressed, and even if the concentration of blue dopant is high, concentration quenching does not occur, and the light emission lifetime is not expected to decrease.
  • organic EL element organic electroluminescent element
  • This organic EL element has a first dopant having a mixed ligand in the light emitting layer and a second dopant, and mixes two or more types of light emission of the first dopant and light emission of a second dopant different from the first dopant. This improves the color rendering of white.
  • the LUMO level of the host compound contained in the light emitting layer is higher than 0.5 eV with respect to the LUMO level of the constituent material of the cathode side adjacent layer of the light emitting layer, Electrons are less likely to be injected into the light emitting layer, resulting in an increase in driving voltage, and the position where recombination of holes and electrons occurs is shifted to the cathode side interface in the light emitting layer, resulting in low luminous efficiency and lifetime performance. Is not enough.
  • JP 2007-27679 A Japanese Unexamined Patent Publication No. 2011-228569
  • a main object of the present invention is to provide an organic EL element that has no increase in voltage, has high luminous efficiency, and can improve the emission lifetime in a white light emitting organic EL element having at least one light emitting layer. It is to be.
  • the inventors of the present invention include a dopant having a specific structure in the light emitting layer, a LUMO (H) level of the host compound of the light emitting layer, and a ligand of the dopant.
  • a dopant having a specific structure in the light emitting layer
  • a LUMO (H) level of the host compound of the light emitting layer and a ligand of the dopant.
  • An organic electroluminescence device having at least one light emitting layer,
  • the light emitting layer contains a host compound and a dopant represented by the structural formula L 1 L 2 L 3 M (where L 1 to L 3 represent a bidentate ligand and M represents a central metal).
  • the LUMO (H) level of the host compound of the light emitting layer the lowest LUMO (L min ) level among the ligands L 1 to L 3 of the dopant, and the constituent material of the cathode side adjacent layer of the light emitting layer
  • an organic electroluminescence device characterized in that the relationship with the LUMO (C) level of the above satisfies the conditional expressions (i) and (ii).
  • an organic EL element that does not increase in voltage, has high luminous efficiency, and has improved luminous lifetime.
  • the present inventors have found that the host compound and the structural formula L 1 L 2 L 3 M (L 1 to L 3 represent bidentate ligands in the light emitting layer, M represents a central metal.), And at least two arbitrarily selected ligands L 1 to L 3 of the dopant are different, and the LUMO of the host compound of the light emitting layer is different.
  • the TT annihilation (triplet-triplet annihilation) is caused by the aggregation of the dopants when the dopant is in a high concentration. It is generally known that Further, in such a system, the dopant is difficult to be uniformly dispersed in the light emitting layer, and the existence distance between the dopants is increased. As a result, when the dopant is responsible for carrier transport, the carrier path is uneven and disturbed, resulting in an increase in voltage. In addition, when the host compound is responsible for carrier transport, the probability of carriers being injected into the dopant is lowered, so the recombination probability is lowered and the light emission efficiency is lowered. Further, the light emission life is reduced accordingly.
  • the light emission efficiency and the light emission lifetime of the organic EL element can be improved by containing a dopant represented by the general formula (1) described later. That is, at least two arbitrarily selected ligand structures out of the plurality of ligands L 1 , L 2 , and L 3 coordinated to the central metal M are made different between the ligands between the dopants. It was found that the steric hindrance becomes stronger and the interaction between the dopants can be relaxed. Thereby, in the system in which the dopant is dispersed in the host compound in the light emitting layer of the organic EL element, the aggregation state is relaxed by relaxation of the interaction between the dopants. It is considered that the problem that the voltage rise due to the nonuniform and disturbed carrier path can be solved, and further the light emission lifetime can be reduced.
  • a dopant represented by the general formula (1) described later That is, at least two arbitrarily selected ligand structures out of the plurality of ligands L 1 , L 2 , and L 3 coordinated
  • the LUMO level is designed to have a specific order as described above, electrons are injected from the cathode-side adjacent layer into the host compound, not the dopant, without a barrier load. And, it is predicted that it is transported without load on the host compound occupying most of the light emitting layer. That is, it is considered that the electron transport between the dopant and the dopant is difficult, and when the electron is injected, the hole and the electron are immediately recombined. As a result, it is presumed that the region where holes and electrons recombine is not the vicinity of the interface between adjacent layers, but the central portion of the light emitting layer, and the region becomes wider.
  • the dopant since the band gap of the dopant is narrower than that of the host compound, when the LUMO level is in a specific order, the dopant basically takes charge of transporting holes.
  • the holes When the dopant is uniformly dispersed in the host compound, the holes are smoothly transported on the dopant, so that the holes are adjacent to the cathode side than the interface on the anode side adjacent layer (for example, hole blocking layer) side. There will be more at the interface on the layer (eg, electron transport layer) side.
  • the LUMO level is in a specific order, electrons are not directly injected into the dopant from the cathode side adjacent layer side interface but are transported on the host compound, so that the recombination region is formed only at the cathode side adjacent layer interface.
  • the LUMO level in the present invention is Gaussian 98 (Gaussian 98, Revision A.11.4, MJ Frisch, et al, Gaussian, Inc., Pittsburgh PA, software for molecular orbital calculation manufactured by Gaussian, USA. 2002.), and by calculating the ionization potential as a value obtained by rounding off the second decimal place of the value (eV unit conversion value) calculated by performing structural optimization using B3LYP / 6-31G * as a keyword can do.
  • This calculation value is effective because the correlation between the calculation value obtained by this method and the experimental value is high.
  • the value calculated as the LUMO level of the compound in which the site bonded to the metal is replaced with hydrogen was used.
  • the other light emitting layer adjacent to the light emitting layer containing the dopant represented by the general formula (2) to the general formula (2-2) has a longer wavelength than the above dopant.
  • the inclusion of a dopant exhibiting light emission transfers energy when the dopant represented by the general formulas (2) to (2-2) returns from the excited state to the ground state to the dopant exhibiting long wavelength light emission. From the ratio, the ratio of the dopant represented by the general formula (2) to the general formula (2-2) is more used as energy for light emission, which is preferable from the viewpoint of efficiently emitting light and improving the lifetime.
  • the dopant (heterodopant) is a compound in which light emission from an excited triplet is observed, specifically, a compound that emits phosphorescence at room temperature (25 ° C.), and has a phosphorescence quantum yield of Although defined as a compound of 0.01 or more at 25 ° C., a preferred phosphorescence quantum yield is 0.1 or more.
  • the phosphorescent quantum yield can be measured by the method described in Spectroscopic II, page 398 (1992 edition, Maruzen) of the Fourth Edition Experimental Chemistry Course 7.
  • the energy transfer type is to obtain light emission from the phosphorescent dopant, and the other is that the phosphorescent dopant becomes a carrier trap, carrier recombination occurs on the phosphorescent dopant, and light emission from the phosphorescent dopant is obtained.
  • the excited state energy of the phosphorescent dopant is required to be lower than the excited state energy of the host compound.
  • the phosphorescent dopant of the present invention has a phosphorescence lifetime of less than 1.4 ⁇ sec at room temperature (25 ° C.) and a phosphorescence quantum yield of 70% or more when dispersed in the light emitting host compound of the light emitting layer.
  • the dopant according to the present invention is a blue phosphorescent dopant and is represented by the following general formula (1).
  • L 1 to L 3 represents a bidentate ligand, and at least two arbitrarily selected among “L 1 to L 3 ” are different.
  • M represents a central metal.
  • Table 1 shows the LUMO levels of the above ligands.
  • a preferred form of the general formula (1) is represented by the following general formula (2).
  • Ring A” and “Ring B” represent a 5- or 6-membered aromatic hydrocarbon ring or aromatic heterocyclic ring.
  • Ar represents an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group.
  • R 1 ” and “R 2 ” each independently represent a hydrogen atom or a substituent, and at least one of “R 1 ” and “R 2 ” is an alkyl group or cycloalkyl group having 2 or more carbon atoms. is there.
  • Ra”, “Rb” and “Rc” are each independently a hydrogen atom, halogen atom, cyano group, alkyl group, alkenyl group, alkynyl group, alkoxy group, amino group, silyl group, arylalkyl group, aryl group Represents a heteroaryl group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group.
  • n a and n c is 1 or 2
  • n b represents an integer of 1-4.
  • “L ′” is one or more of monoanionic bidentate ligands coordinated to “M”, and “M” represents a central metal.
  • m ′ represents an integer of 1 or 2
  • n ′ represents an integer of 1 or 2
  • m ′ + n ′ is 3.
  • “L ′” is a different ligand.
  • R 1 and R 2 represent a substituent, it means that they may have a substituent as long as they do not impair the function of the dopant according to the present invention.
  • At least one of “R 1 ” and “R 2 ” represents an alkyl group or cycloalkyl group having 2 or more carbon atoms, and the upper limit of the number of carbon atoms is within a range not impairing the function of the dopant according to the present invention. If it is, it will not specifically limit, Preferably it is C10 or less, More preferably, it is 6 or less.
  • the groups represented by “Ra”, “Rb” and “Rc” may further have a substituent as long as they do not inhibit the function of the dopant according to the present invention. And the same substituents represented by “Rd ′”, “Rd ′′” and “Rd ′ ′′”.
  • a preferred form of the general formula (2) is represented by the following general formula (2-1).
  • “Ar” represents an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group.
  • “R 1 ” and “R 2 ” each independently represent a hydrogen atom or a substituent, and at least one of “R 1 ” and “R 2 ” is an alkyl group or cycloalkyl group having 2 or more carbon atoms. is there.
  • Ra”, “Rb” and “Rc” are each independently a hydrogen atom, halogen atom, cyano group, alkyl group, alkenyl group, alkynyl group, alkoxy group, amino group, silyl group, arylalkyl group, aryl group Represents a heteroaryl group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group.
  • n a and n c is 1 or 2
  • n b represents an integer of 1-4.
  • “L ′” is one or more of monoanionic bidentate ligands coordinated to “M”, and “M” represents a central metal.
  • m ′ represents an integer of 1 or 2
  • n ′ represents an integer of 1 or 2
  • m ′ + n ′ is 3.
  • “L ′” is a different ligand.
  • R 1 and R 2 represent a substituent, it means that they may have a substituent as long as they do not impair the function of the dopant according to the present invention.
  • At least one of “R 1 ” and “R 2 ” represents an alkyl group or cycloalkyl group having 2 or more carbon atoms, and the upper limit of the number of carbon atoms is within a range not impairing the function of the dopant according to the present invention. If it is, it will not specifically limit, Preferably it is C10 or less, More preferably, it is 6 or less.
  • the groups represented by “Ra”, “Rb” and “Rc” may further have a substituent as long as they do not inhibit the function of the dopant according to the present invention. And the same substituents represented by “Rd ′”, “Rd ′′” and “Rd ′ ′′”.
  • Rd ′”, “Rd ′′” and “Rd ′ ′′” each independently represent a linking site with another group, a hydrogen atom or a substituent, and each “Rd ′”, “Rd” ”And“ Rd ′ ′′ ”may be the same or different, and“ Rd ′ ”,“ Rd ′′ ”, and“ Rd ′ ′′ ”may be bonded to each other to form a ring.
  • Rd ′ When “Rd ′”, “Rd ′′” and “Rd ′ ′′” represent a substituent, it means that the substituent may be present as long as the function of the dopant according to the present invention is not impaired.
  • substituent include alkyl groups (for example, methyl group, ethyl group, propyl group, isopropyl group, tert-butyl group, pentyl group, hexyl group, octyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, etc.
  • Alkenyl groups eg, vinyl groups, allyl groups, etc.
  • alkynyl groups eg, ethynyl groups, propargyl groups, etc.
  • non-aromatic hydrocarbon ring groups eg, cycloalkyl groups (eg, cyclopentyl groups, cyclohexyl groups, etc.)
  • a cycloalkoxy group eg, cyclopentyloxy group, cyclohexyloxy group, etc.
  • cycloalkyl Thio group for example, cyclopentylthio group, cyclohexylthio group, etc.
  • tetrahydronaphthalene ring 9,10-dihydroanthracene ring, monovalent group derived from biphenylene ring, etc.
  • non-aromatic heterocyclic group for example, epoxy Ring, aziridine ring, thiirane ring, oxetane ring, a
  • aromatic heterocyclic group for example, silole ring, furan ring, thiophene ring, oxazole ring, pyrrole ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, triazine ring, oxadiazole ring, triazole ring, imidazole Ring, pyrazole ring, thiazole ring, indole ring, benzimidazole ring, benzthiazole ring, benzoxazole ring, quinoxaline ring, quinazoline ring, phthalazine ring, thienothiophene ring, carbazole ring, azacarbazole ring (carbon atoms constituting carbazole ring) Any one or more of carbon atoms constituting a dibenzosilole ring, dibenzofuran ring, dibenzothiophene ring, benzothi
  • M represents a central metal, and examples thereof include Os, Ir, and Pt.
  • the compounds represented by the general formulas (2) and (2-1) according to the present invention can be synthesized by referring to known methods described in International Publication No. 2006-121811, etc.
  • “Ar” represents an aromatic hydrocarbon ring group, an aromatic heterocyclic group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group.
  • “R 1 to R 4 ” each independently represents a hydrogen atom or a substituent, and at least one of “R 1 ” and “R 2 ” and at least one of “R 3 ” and “R 4 ” are each carbon.
  • Ra”, “Rb”, “Ra ′” and “Rb ′” each independently represent a hydrogen atom, a halogen atom, a cyano group, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an amino group, a silyl group, An arylalkyl group, an aryl group, a heteroaryl group, a non-aromatic hydrocarbon ring group or a non-aromatic heterocyclic group is represented. n represents an integer of 1 or 2.
  • At least one of “R 1 ” and “R 2 ” and at least one of “R 3 ” and “R 4 ” represents an alkyl group or cycloalkyl group having 2 or more carbon atoms, and the upper limit of the number of carbon atoms is The number of carbon atoms is not particularly limited as long as it does not hinder the function of the dopant according to the present invention, and it is preferably 10 or less, more preferably 6 or less.
  • the group represented by “Ra”, “Rb”, “Ra ′” and “Rb ′” may further have a substituent as long as the function of the dopant according to the present invention is not impaired.
  • substituents include the same substituents represented by the aforementioned “Rd ′”, “Rd ′′” and “Rd ′ ′′”.
  • the host compound used in the light emitting layer is a phosphorescent phosphorous compound at a room temperature (25 ° C.) having a mass ratio of 20% or more among the compounds contained in the light emitting layer.
  • a photon yield is defined as a compound of less than 0.1.
  • the phosphorescence quantum yield is preferably less than 0.01.
  • a host compound which can be used for this invention Although the compound conventionally used with an organic EL element can be used, The host compound with respect to the blue phosphorescence emission dopant of the light emitting layer of the organic EL element of this invention In particular, those having a structure represented by the following general formula (3) are preferable.
  • X represents NR ′, O, S, CR′R ′′ or SiR′R ′′.
  • R 1 represents a carbazolyl group having a phenyl group or an aromatic heterocyclic group.
  • R 2 represents a carbazolyl group which may have a substituent.
  • R ′ and R ′′ each independently represents a hydrogen atom or a substituent.
  • R ′ and R ′′ represent a substituent, it means that the substituent may have a substituent as long as the function as a host compound according to the present invention is not impaired.
  • substituents include alkyl groups (for example, methyl group, ethyl group, propyl group, isopropyl group, t-butyl group, pentyl group, hexyl group, octyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group).
  • cycloalkyl group eg cyclopentyl group, cyclohexyl group etc.
  • alkenyl group eg vinyl group, allyl group etc.
  • alkynyl group eg ethynyl group, propargyl group etc.
  • aromatic hydrocarbon ring group Also called aromatic carbocyclic group, aryl group, etc., for example, phenyl group, p-chlorophenyl group, mesityl group, tolyl group, Ryl group, naphthyl group, anthryl group, azulenyl group, acenaphthenyl group, fluorenyl group, phenanthryl group, indenyl group, pyrenyl group, biphenylyl group, etc.), aromatic heterocyclic group (for example, pyridyl group, pyrimidinyl group, furyl group, pyrrolyl) Group, imidazolyl group, benzoimid
  • examples of the aromatic heterocyclic group contained in “R 1 ” include a pyridyl group, pyrimidinyl group, furyl group, pyrrolyl group, imidazolyl group, benzimidazolyl group, pyrazolyl group, pyrazinyl group, triazolyl group ( For example, 1,2,4-triazol-1-yl group, 1,2,3-triazol-1-yl group, etc.), oxazolyl group, benzoxazolyl group, thiazolyl group, isoxazolyl group, isothiazolyl group, furazanyl group , Thienyl group, quinolyl group, benzofuryl group, dibenzofuryl group, benzothienyl group, dibenzothienyl group, indolyl group, carbazolyl group, carbolinyl group, diazacarbazolyl group (the carbon atom constituting the carboline ring of the carboliny
  • the carbazolyl group represented by “R 2 ” may have a substituent represented by R ′ and R ′′ in “X” in General Formula (3). Synonymous with group.
  • X is preferably NR ′ or O
  • R ′ is an aromatic hydrocarbon group (also referred to as an aromatic carbocyclic group, an aryl group, etc., for example, a phenyl group, a p-chlorophenyl group, Mesityl, tolyl, xylyl, naphthyl, anthryl, azulenyl, acenaphthenyl, fluorenyl, phenanthryl, indenyl, pyrenyl, biphenylyl) or aromatic heterocyclic groups (eg furyl, thienyl) Group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, imidazolyl group, pyrazolyl group, thiazolyl group, quinazolinyl group, phthalazinyl group and the like are particularly preferable.
  • aromatic hydrocarbon group also
  • aromatic hydrocarbon group and aromatic heterocyclic group each may have a substituent represented by R ′ or R ′′ in “X” of the general formula (3).
  • fluorescent dopants also referred to as fluorescent compounds
  • phosphorescent dopants also referred to as phosphorescent emitters, phosphorescent compounds, phosphorescent compounds, etc.
  • Fluorescent dopants include coumarin dyes, pyran dyes, cyanine dyes, croconium dyes, squalium dyes, oxobenzanthracene dyes, fluorescein dyes, rhodamine dyes, pyrylium dyes, perylene dyes, stilbene dyes , Polythiophene dyes, rare earth complex phosphors, and the like, and compounds having a high fluorescence quantum yield, such as laser dyes, are not particularly limited, and are used for the light emitting layer of an organic EL device. It can select suitably from the well-known thing to be used.
  • the phosphorescent dopant is preferably a complex compound containing a group 8-10 metal in the periodic table of elements, more preferably an iridium compound, an osmium compound, a platinum compound (platinum complex compound), or a rare earth complex. Among them, the most preferable is an iridium compound.
  • the other light emitting layer adjacent to the light emitting layer containing the said blue dopant contains the green dopant and red dopant which are dopants which show light emission longer wavelength than a blue dopant. It is preferable.
  • the light emitting layer according to the present invention is a layer that emits light by recombination of electrons and holes injected from the electrode, the electron transport layer, or the hole transport layer. If the light emitting material (dopant) contained in the light emitting layer concerning this invention satisfy
  • the total thickness of the light emitting layers in the present invention is preferably in the range of 1 to 100 nm, and more preferably 30 nm or less because a lower driving voltage can be obtained.
  • the sum total of the film thickness of the light emitting layer as used in the field of this invention is a film thickness also including the said intermediate
  • the film thickness of each light emitting layer is preferably adjusted in the range of 1 to 50 nm, more preferably in the range of 1 to 20 nm. There is no particular limitation on the relationship between the film thicknesses of the blue, green and red light emitting layers.
  • the above-described host compound or light-emitting material is formed by forming a film by a known thinning method such as a vacuum evaporation method, a spin coating method, a casting method, an LB method, or an inkjet method. it can.
  • a plurality of light emitting materials may be mixed in each light emitting layer, or a phosphorescent light emitting material and a fluorescent light emitting material may be mixed and used in the same light emitting layer.
  • the constitution of the light emitting layer preferably contains a host compound and a dopant and emits light from the dopant.
  • Recombination region Of the entire region of the light emitting layer, the region contributing to light emission (recombination region) can be calculated from the value of ⁇ PL / ⁇ EL and the width of the region can be estimated from the calculation result.
  • ⁇ EL and ⁇ PL respectively represent the intensity decay rates of electroluminescence (EL) and photoluminescence (PL) before and after driving, and can be represented by the following equations.
  • ⁇ EL 1 ⁇ [EL (after driving) / EL (before driving)]
  • ⁇ PL 1 ⁇ [PL (after driving) / PL (before driving)]
  • the PL value after the PL driving is measured in a state after driving the organic EL element until the light emission luminance is about half from the initial luminance ( ⁇ EL is about 0.5).
  • ⁇ PL represents a recombination region with respect to the entire light emitting layer, it is estimated that the recombination region contributing to light emission is narrow when ⁇ PL / ⁇ EL is small, and light emission occurs when ⁇ PL / ⁇ EL is large. It is presumed that the recombination region contributing is wide.
  • 1A to 1D are schematic views showing respective regions in the layer thickness direction of the light emitting layer 1, and the left-right direction in FIG. 1 corresponds to the layer thickness direction.
  • the light emitting layer 1 is partitioned into a region contributing to light emission (recombination region 10) and a region 12 not contributing to light emission. Accordingly, the recombination region 10 is a measurement target for “EL before driving”.
  • the PL before driving is the measurement target of the region 20 representing the entire light emitting layer.
  • “PL after driving” indicates that the remaining region 22 obtained by subtracting the non-light-emitting region 16 from the region 20 representing the entire light-emitting layer in accordance with the formation of the non-light-emitting region 16 in the recombination region 10 is measured. It becomes.
  • An injection layer is a layer provided between an electrode and an organic layer in order to reduce drive voltage and improve light emission luminance.
  • Organic EL element and its forefront of industrialization (issued by NTT Corporation on November 30, 1998) 2), Chapter 2, “Electrode Materials” (pages 123 to 166) in detail, and includes a hole injection layer (anode buffer layer) and an electron injection layer (cathode buffer layer).
  • the injection layer is provided as necessary, and may be present between the anode and the light emitting layer or the hole transport layer and between the cathode and the light emitting layer or the electron transport layer as described above.
  • hole injection layer anode buffer layer
  • hole injection layer anode buffer layer
  • copper phthalocyanine is used.
  • examples thereof include a phthalocyanine buffer layer represented by an oxide, an oxide buffer layer represented by vanadium oxide, an amorphous carbon buffer layer, and a polymer buffer layer using a conductive polymer such as polyaniline (emeraldine) or polythiophene.
  • cathode buffer layer Details of the electron injection layer (cathode buffer layer) are also described in JP-A-6-325871, JP-A-9-17574, JP-A-10-74586, and the like. Specifically, strontium, aluminum, etc.
  • Metal buffer layer typified by lithium
  • alkali metal compound buffer layer typified by lithium fluoride
  • alkaline earth metal compound buffer layer typified by magnesium fluoride
  • oxide buffer layer typified by aluminum oxide, etc. .
  • the injection layer is preferably a very thin film, and the film thickness is preferably in the range of 0.1 nm to 5 ⁇ m although it depends on the material.
  • ⁇ Blocking layer hole blocking layer, electron blocking layer>
  • the blocking layer is provided as necessary in addition to the basic constituent layer of the organic compound thin film as described above. For example, it is described in JP-A Nos. 11-204258 and 11-204359, and “Organic EL elements and the forefront of industrialization (published by NTT Corporation on Nov. 30, 1998)”. There is a hole blocking (hole blocking) layer.
  • the hole blocking layer has a function of an electron transport layer in a broad sense, and is made of a hole blocking material having a function of transporting electrons and a very small ability to transport holes. By blocking the holes, the probability of recombination of electrons and holes can be improved. Moreover, the structure of the electron carrying layer mentioned later can be used as a hole-blocking layer concerning this invention as needed.
  • the hole blocking layer of the organic EL device of the present invention is preferably provided adjacent to the light emitting layer.
  • the hole blocking layer preferably contains an azacarbazole derivative.
  • the light emitting layer having the shortest wavelength of light emission is preferably closest to the anode among all the light emitting layers.
  • 50% by mass or more of the compound contained in the hole blocking layer provided at the position has an ionization potential of 0.3 eV or more larger than the host compound of the shortest wave emitting layer.
  • the ionization potential is defined by the energy required to emit electrons at the HOMO (highest occupied molecular orbital) level of the compound to the vacuum level.
  • the ionization potential is obtained by the method shown in (1) and (2) below. Can do.
  • Gaussian98 (Gaussian98, Revision A.11.4, MJ Frisch, et al, Gaussian, Inc., Pittsburgh PA, 2002.), which is software for molecular orbital calculation manufactured by Gaussian, USA.
  • the ionization potential can be obtained as a value obtained by rounding off the second decimal place of a value (eV unit converted value) calculated by performing structure optimization using B3LYP / 6-31G * as a keyword. This calculation value is effective because the correlation between the calculation value obtained by this method and the experimental value is high.
  • the ionization potential can also be obtained by a method of direct measurement by photoelectron spectroscopy.
  • a low energy electron spectrometer “Model AC-1” manufactured by Riken Keiki Co., Ltd. or a method known as ultraviolet photoelectron spectroscopy can be suitably used.
  • the electron blocking layer has a function of a hole transport layer in a broad sense, and is made of a material having a function of transporting holes while having a remarkably small ability to transport electrons. The probability of recombination of electrons and holes can be improved by blocking. Moreover, the structure of the positive hole transport layer mentioned later can be used as an electron blocking layer as needed.
  • the film thickness of the hole blocking layer and the electron transport layer according to the present invention is preferably 3 nm to 100 nm, more preferably 5 nm to 30 nm.
  • the hole transport layer is made of a hole transport material having a function of transporting holes, and in a broad sense, a hole injection layer and an electron blocking layer are also included in the hole transport layer.
  • the hole transport layer can be provided as a single layer or a plurality of layers.
  • the hole transport material has any one of hole injection or transport and electron barrier properties, and may be either organic or inorganic.
  • triazole derivatives oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives
  • Examples thereof include stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers, particularly thiophene oligomers.
  • the above-mentioned materials can be used as the hole transport material, but it is preferable to use a porphyrin compound, an aromatic tertiary amine compound and a styrylamine compound, particularly an aromatic tertiary amine compound.
  • aromatic tertiary amine compounds and styrylamine compounds include N, N, N ′, N′-tetraphenyl-4,4′-diaminophenyl; N, N′-diphenyl-N, N′— Bis (3-methylphenyl)-[1,1′-biphenyl] -4,4′-diamine (TPD); 2,2-bis (4-di-p-tolylaminophenyl) propane; 1,1-bis (4-di-p-tolylaminophenyl) cyclohexane; N, N, N ′, N′-tetra-p-tolyl-4,4′-diaminobiphenyl; 1,1-bis (4-di-p-tolyl) Aminophenyl) -4-phenylcyclohexane; bis (4-dimethylamino-2-methylphenyl) phenylmethane; bis (4-di-p-tolylaminoph
  • polymer materials in which these materials are introduced into polymer chains or these materials are used as polymer main chains can also be used.
  • inorganic compounds such as p-type-Si and p-type-SiC can also be used as the hole injection material and the hole transport material.
  • JP-A-11-251067 J. Org. Huang et. al.
  • a so-called p-type hole transport material described in a book (Applied Physics Letters 80 (2002), p. 139) can also be used.
  • these materials are preferably used because a light-emitting element with higher efficiency can be obtained.
  • the hole transport layer is formed by thinning the hole transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method. Can do.
  • the thickness of the hole transport layer is not particularly limited, but is usually about 5 nm to 5 ⁇ m, preferably 5 nm to 200 nm.
  • the hole transport layer may have a single layer structure composed of one or more of the above materials.
  • a hole transport layer having a high p property doped with impurities can be used.
  • examples thereof include JP-A-4-297076, JP-A-2000-196140, and JP-A-2001-102175. Appl. Phys. 95, 5773 (2004), and the like.
  • the electron transport layer is made of a material having a function of transporting electrons, and in a broad sense, an electron injection layer and a hole blocking layer are also included in the electron transport layer.
  • the electron transport layer can be provided as a single layer or a plurality of layers.
  • electrons injected from the cathode are used.
  • Any material can be used as long as it has a function of transmitting to the light-emitting layer, and any material can be selected from conventionally known compounds. For example, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyrans can be used.
  • Dioxide derivatives, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, oxadiazole derivatives and the like can be mentioned.
  • a thiadiazole derivative in which the oxygen atom of the oxadiazole ring is substituted with a sulfur atom, or a quinoxaline derivative having a quinoxaline ring known as an electron withdrawing group can also be used as an electron transport material.
  • a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used.
  • metal complexes of 8-quinolinol derivatives such as tris (8-quinolinol) aluminum (Alq), tris (5,7-dichloro-8-quinolinol) aluminum, tris (5,7-dibromo-8-quinolinol) aluminum Tris (2-methyl-8-quinolinol) aluminum, tris (5-methyl-8-quinolinol) aluminum, bis (8-quinolinol) zinc (Znq), and the like, and the central metals of these metal complexes are In, Mg, Metal complexes replaced with Cu, Ca, Sn, Ga or Pb can also be used as the electron transport material.
  • metal-free or metal phthalocyanine or those having terminal ends substituted with an alkyl group or a sulfonic acid group can be preferably used as the electron transporting material.
  • the distyrylpyrazine derivative exemplified as the material for the light emitting layer can also be used as an electron transport material, and an inorganic semiconductor such as n-type-Si, n-type-SiC, etc. as in the case of the hole injection layer and the hole transport layer. Can also be used as an electron transporting material.
  • the electron transport layer can be formed by thinning the electron transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, a printing method including an ink jet method, or an LB method. .
  • the thickness of the electron transport layer is not particularly limited, but is usually about 5 nm to 5 ⁇ m, preferably 5 nm to 200 nm.
  • the electron transport layer may have a single layer structure composed of one or more of the above materials.
  • an electron transport layer having a high n property doped with impurities can also be used.
  • examples thereof include JP-A-4-297076, JP-A-10-270172, JP-A-2000-196140, 2001-102175, J.A. Appl. Phys. 95, 5773 (2004), and the like.
  • an electrode material made of a metal, an alloy, an electrically conductive compound and a mixture thereof having a high work function (4 eV or more) is preferably used.
  • electrode substances include metals such as Au, and conductive transparent materials such as CuI, indium tin oxide (ITO), SnO 2 , and ZnO.
  • conductive transparent materials such as CuI, indium tin oxide (ITO), SnO 2 , and ZnO.
  • an amorphous material such as IDIXO (In 2 O 3 —ZnO) capable of forming a transparent conductive film may be used.
  • a thin film may be formed by depositing these electrode materials by a method such as vapor deposition or sputtering, and a pattern having a desired shape may be formed by photolithography, or when the pattern accuracy is not so high (about 100 ⁇ m or more) ), A pattern may be formed through a mask having a desired shape when the electrode material is deposited or sputtered. Or when using the substance which can be apply
  • the transmittance is greater than 10%, and the sheet resistance as the anode is preferably several hundred ⁇ / ⁇ or less.
  • the film thickness depends on the material, it is usually selected in the range of 10 nm to 1000 nm, preferably 10 nm to 200 nm.
  • cathode a material having a low work function (4 eV or less) metal (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof as an electrode material is used.
  • electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3 ) Mixtures, indium, lithium / aluminum mixtures, rare earth metals and the like.
  • a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function than this for example, a magnesium / silver mixture, Magnesium / aluminum mixtures, magnesium / indium mixtures, aluminum / aluminum oxide (Al 2 O 3 ) mixtures, lithium / aluminum mixtures, aluminum and the like are preferred.
  • the cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.
  • the sheet resistance as a cathode is preferably several hundred ⁇ / ⁇ or less, and the film thickness is usually selected in the range of 10 nm to 5 ⁇ m, preferably 50 nm to 200 nm.
  • the film thickness is usually selected in the range of 10 nm to 5 ⁇ m, preferably 50 nm to 200 nm.
  • a transparent or semi-transparent cathode can be produced by producing the conductive transparent material mentioned in the description of the anode on the cathode after producing the metal with a film thickness of 1 nm to 20 nm. By applying this, an element in which both the anode and the cathode are transmissive can be manufactured.
  • a support substrate (hereinafter also referred to as a substrate, substrate, substrate, support, etc.) that can be used in the organic EL device of the present invention, there is no particular limitation on the type of glass, plastic, etc., and it is transparent. May be opaque. When extracting light from the support substrate side, the support substrate is preferably transparent. Examples of the transparent support substrate preferably used include glass, quartz, and a transparent resin film. A particularly preferable support substrate is a resin film capable of giving flexibility to the organic EL element.
  • polyesters such as polyethylene terephthalate (PET) and polyethylene naphthalate (PEN), polyethylene, polypropylene, cellophane, cellulose diacetate, cellulose triacetate, cellulose acetate butyrate, cellulose acetate propionate (CAP), Cellulose esters such as cellulose acetate phthalate (TAC) and cellulose nitrate or derivatives thereof, polyvinylidene chloride, polyvinyl alcohol, polyethylene vinyl alcohol, syndiotactic polystyrene, polycarbonate, norbornene resin, polymethylpentene, polyether ketone, polyimide , Polyethersulfone (PES), polyphenylene sulfide, polysulfone , Polyetherimide, polyetherketoneimide, polyamide, fluororesin, nylon, polymethylmethacrylate, acrylic or polyarylates, cyclone resins such as Arton (trade name, manufactured by JSR) or Appel (trade
  • the surface of the resin film may be formed with an inorganic film, an organic film, or a hybrid film of both, and the barrier film has a water vapor permeability of 0.01 g / (m 2 ⁇ 24 h ⁇ atm) or less. Further, it is a high barrier film having an oxygen permeability of 1 ⁇ 10 ⁇ 3 ml / (m 2 ⁇ 24 h) or less and a water vapor permeability of 1 ⁇ 10 ⁇ 5 g / (m 2 ⁇ 24 h) or less. preferable.
  • any material may be used as long as it has a function of suppressing entry of elements that cause deterioration of elements such as moisture and oxygen.
  • silicon oxide, silicon dioxide, silicon nitride, or the like can be used.
  • stacking order of an inorganic layer and an organic layer It is preferable to laminate
  • the method for forming the barrier film is not particularly limited.
  • the vacuum deposition method, sputtering method, reactive sputtering method, molecular beam epitaxy method, cluster ion beam method, ion plating method, plasma polymerization method, atmospheric pressure plasma weight A combination method, a plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, and the like can be used, but an atmospheric pressure plasma polymerization method as described in JP-A-2004-68143 is particularly preferable.
  • the opaque support substrate examples include metal plates such as aluminum and stainless steel, films, opaque resin substrates, ceramic substrates, and the like.
  • the external extraction efficiency at room temperature of light emission of the organic EL device of the present invention is preferably 1% or more, more preferably 5% or more.
  • the external extraction quantum efficiency (%) the number of photons emitted to the outside of the organic EL element / the number of electrons sent to the organic EL element ⁇ 100.
  • a hue improving filter such as a color filter may be used in combination, or a color conversion filter for converting the emission color from the organic EL element into multiple colors using a phosphor may be used in combination.
  • the ⁇ max of light emission of the organic EL element is preferably 480 nm or less.
  • the sealing member may be disposed so as to cover the display area of the organic EL element, and may be a concave plate shape or a flat plate shape. Further, transparency and electrical insulation are not particularly limited. Specific examples include a glass plate, a polymer plate / film, and a metal plate / film. Examples of the glass plate include soda-lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, and quartz.
  • polymer plate examples include polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, and polysulfone.
  • metal plate examples include those made of one or more metals or alloys selected from the group consisting of stainless steel, iron, copper, aluminum, magnesium, nickel, zinc, chromium, titanium, molybdenum, silicon, germanium, and tantalum.
  • a polymer film and a metal film can be preferably used because the element can be thinned.
  • the polymer film has an oxygen permeability measured by a method according to JIS K 7126-1987 of 1 ⁇ 10 ⁇ 3 ml / (m 2 ⁇ 24 h) or less, and measured by a method according to JIS K 7129-1992.
  • the water vapor permeability (25 ⁇ 0.5 ° C., relative humidity (90 ⁇ 2)% RH is preferably 1 ⁇ 10 ⁇ 3 g / (m 2 ⁇ 24 h) or less.
  • adhesives include photo-curing and thermosetting adhesives having reactive vinyl groups such as acrylic acid oligomers and methacrylic acid oligomers, and moisture curing adhesives such as 2-cyanoacrylates. Can be mentioned. Moreover, heat
  • coating of the adhesive agent to a sealing part may use commercially available dispenser, and may print like screen printing.
  • the electrode and the organic layer are coated on the outside of the electrode facing the support substrate with the organic layer interposed therebetween, and an inorganic or organic layer is formed in contact with the support substrate to form a sealing film.
  • the material for forming the film may be any material that has a function of suppressing infiltration of elements that cause deterioration of elements such as moisture and oxygen.
  • silicon oxide, silicon dioxide, silicon nitride, or the like may be used. it can.
  • vacuum deposition method sputtering method, reactive sputtering method, molecular beam epitaxy method, cluster ion beam method, ion plating method, plasma polymerization method, atmospheric pressure plasma
  • a polymerization method a plasma CVD method, a laser CVD method, a thermal CVD method, a coating method, or the like can be used.
  • an inert gas such as nitrogen or argon, or an inert liquid such as fluorinated hydrocarbon or silicon oil can be injected in the gas phase and liquid phase.
  • a vacuum can also be used.
  • a hygroscopic compound can also be enclosed inside. Examples of the hygroscopic compound include metal oxides (eg, sodium oxide, potassium oxide, calcium oxide, barium oxide, magnesium oxide, aluminum oxide), sulfates (eg, sodium sulfate, calcium sulfate, magnesium sulfate, cobalt sulfate).
  • metal halides for example, calcium chloride, magnesium chloride, cesium fluoride, tantalum fluoride, cerium bromide, magnesium bromide, barium iodide, magnesium iodide, etc.
  • perchloric acids for example, perchloric acid
  • anhydrous salts are preferably used in sulfates, metal halides and perchloric acids.
  • a protective film or a protective plate may be provided on the outer side of the sealing film or the sealing film on the side facing the support substrate with the organic layer interposed therebetween.
  • the mechanical strength is not necessarily high. Therefore, it is preferable to provide such a protective film and a protective plate.
  • the same glass plate, polymer plate / film, metal plate / film, etc. used for sealing can be used. It is preferable to use it.
  • the organic EL element emits light inside a layer having a refractive index higher than that of air (refractive index is about 1.7 to 2.1), and can extract only about 15% to 20% of the light generated in the light emitting layer. It is generally said that there is no. This is because light incident on the interface (interface between the transparent substrate and air) at an angle ⁇ greater than the critical angle causes total reflection and cannot be taken out of the device, or between the transparent electrode or light emitting layer and the transparent substrate. This is because the light undergoes total reflection between the light and the light, and the light is guided through the transparent electrode or the light emitting layer.
  • a method for improving the light extraction efficiency for example, a method of forming irregularities on the surface of the transparent substrate to prevent total reflection at the interface between the transparent substrate and the air (US Pat. No. 4,774,435), A method for improving efficiency by giving light condensing property to a substrate (Japanese Patent Laid-Open No. 63-314795), a method of forming a reflective surface on the side surface of an element (Japanese Patent Laid-Open No. 1-220394), and light emission from the substrate A method of forming an antireflection film by introducing a flat layer having an intermediate refractive index between the bodies (Japanese Patent Laid-Open No.
  • a method of introducing a flat layer having a lower refractive index than the substrate between the substrate and the light emitter, or a substrate, transparent A method of forming a diffraction grating between any layers of the electrode layer and the light emitting layer (including between the substrate and the outside) can be suitably used. In the present invention, by combining these means, it is possible to obtain an element having higher luminance or durability.
  • the low refractive index layer include aerogel, porous silica, magnesium fluoride, and a fluorine-based polymer. Since the refractive index of the transparent substrate is generally about 1.5 to 1.7, the low refractive index layer preferably has a refractive index of about 1.5 or less. Furthermore, it is more preferable that it is 1.35 or less.
  • the thickness of the low refractive index medium is preferably at least twice the wavelength in the medium. This is because the effect of the low refractive index layer is diminished when the thickness of the low refractive index medium is about the wavelength of light and the electromagnetic wave that has exuded by evanescent enters the substrate.
  • the method of introducing a diffraction grating into an interface or any medium that causes total reflection is characterized by a high effect of improving light extraction efficiency.
  • This method uses the property that the diffraction grating can change the direction of light to a specific direction different from refraction by so-called Bragg diffraction such as first-order diffraction and second-order diffraction.
  • the light that cannot be emitted due to total reflection between layers, etc. is diffracted by introducing a diffraction grating into any layer or medium (in the transparent substrate or transparent electrode), and the light is I want to take it out.
  • the introduced diffraction grating desirably has a two-dimensional periodic refractive index.
  • the position where the diffraction grating is introduced may be in any of the layers or in the medium (in the transparent substrate or in the transparent electrode), but is preferably in the vicinity of the organic light emitting layer where light is generated.
  • the period of the diffraction grating is preferably about 1/2 to 3 times the wavelength of light in the medium.
  • the arrangement of the diffraction grating is preferably two-dimensionally repeated, such as a square lattice, a triangular lattice, or a honeycomb lattice.
  • the organic EL device of the present invention can be processed on the light extraction side of the substrate, for example, by providing a microlens array-like structure, or combined with a so-called condensing sheet, for example, in a specific direction, for example, the device light emitting surface
  • luminance in a specific direction can be raised by condensing in a front direction.
  • quadrangular pyramids having a side of 30 ⁇ m and an apex angle of 90 degrees are two-dimensionally arranged on the light extraction side of the substrate. One side is preferably 10 ⁇ m to 100 ⁇ m.
  • the condensing sheet for example, a sheet that is put into practical use in an LED backlight of a liquid crystal display device can be used.
  • a brightness enhancement film (BEF) manufactured by Sumitomo 3M Limited can be used.
  • the shape of the prism sheet for example, the base material may be formed with a ⁇ -shaped stripe having a vertex angle of 90 degrees and a pitch of 50 ⁇ m, or the vertex angle is rounded and the pitch is changed randomly. Other shapes may be used.
  • a light diffusing plate and a film with a condensing sheet.
  • a diffusion film (light-up) manufactured by Kimoto Co., Ltd. can be used.
  • Organic compound thin films can be made by vapor deposition or wet processes (spin coating, casting, ink jet, spray coating, blade coating, air knife coating, wire bar coating, gravure coating, flexographic coating, etc. Coating method, reverse coating method, reverse roll coating method, extrusion coating method, etc.). Different film forming methods may be applied for each layer.
  • the vapor deposition conditions vary depending on the type of compound used, but generally a boat heating temperature of 50 to 450 ° C., a degree of vacuum of 10 ⁇ 6 to 10 ⁇ 2 Pa, and a vapor deposition rate of 0.01 to It is desirable to select appropriately within a range of 50 nm / second, a substrate temperature of ⁇ 50 to 300 ° C., and a film thickness of 0.1 nm to 5 ⁇ m, preferably 5 to 200 nm. In the case of the vapor deposition method, it is preferable to consistently produce from the hole injection layer to the cathode by one evacuation, but it may be taken out halfway and subjected to different film forming methods.
  • a thin film made of a cathode material is formed thereon by a method such as vapor deposition or sputtering so as to have a film thickness of 1 ⁇ m or less, preferably in the range of 50 to 200 nm.
  • a metal, an alloy, an electrically conductive compound and a mixture thereof having a low melting point may be melted and applied, or a metal dispersion or the like may be applied.
  • the organic EL element of the present invention can be used as a display device, a display, and various light emission sources.
  • lighting devices home lighting, interior lighting
  • clock and liquid crystal backlights billboard advertisements, traffic lights, light sources of optical storage media, light sources of electrophotographic copying machines, light sources of optical communication processors, light Examples include, but are not limited to, a light source of a sensor.
  • the light source can be effectively used for a backlight of a liquid crystal display device and a light source for illumination.
  • patterning may be performed by a metal mask, an ink jet printing method, or the like as needed during film formation. In the case of patterning, only the electrode may be patterned, the electrode and the light emitting layer may be patterned, or the entire layer of the element may be patterned. In the fabrication of the element, a conventionally known method is used. Can do.
  • organic EL element As an anode, a substrate (NA Technoglass NA45) formed by depositing ITO (indium tin oxide) with a thickness of 100 nm on a 100 mm ⁇ 100 mm ⁇ 1.1 mm glass substrate After patterning, the transparent support substrate provided with the ITO transparent electrode was ultrasonically cleaned with isopropyl alcohol, dried with dry nitrogen gas, and subjected to UV ozone cleaning for 5 minutes.
  • ITO indium tin oxide
  • This transparent support substrate is fixed to a substrate holder of a commercially available vacuum deposition apparatus, while 200 mg of HT-30 having the following structure is placed in a molybdenum resistance heating boat, and HT- 200 mg of a-1 is put in another molybdenum resistance heating boat, 200 mg of a comparative compound having the structure shown below is put in another resistance heating boat made of molybdenum, and Ir- 200 mg of ET-7 having the structure shown below was put in another resistance heating boat made of molybdenum and attached to a vacuum deposition apparatus.
  • the pressure in the vacuum chamber was reduced to 4 ⁇ 10 ⁇ 4 Pa and then heated by energizing a heating boat containing HT-30, and deposited on the transparent support substrate at a deposition rate of 0.1 nm / second.
  • a hole injection layer was provided.
  • the heating boat containing HT-2 was energized and heated, and deposited on the hole injection layer at a deposition rate of 0.1 nm / second to provide a hole transport layer having a thickness of 30 nm.
  • the heating boat containing a-1, comparative compound, Ir-1, and Ir-6 was energized and heated, and the deposition rates were 0.1 nm / second, 0.02 nm / second, 0.0001 nm / second, 0, respectively. Co-deposited on the hole transport layer at a rate of .0002 nm / second to provide a 40 nm thick light emitting layer. Further, an electron transport layer (ETL) which is heated by energizing a heating boat containing ET-7, deposited on the light emitting layer at a deposition rate of 0.1 nm / second, and serving as a cathode side adjacent layer of the light emitting layer having a thickness of 30 nm. ).
  • ETTL electron transport layer
  • lithium fluoride was vapor-deposited with a film thickness of 0.5 nm, and aluminum was vapor-deposited with a film thickness of 110 nm to form a cathode, whereby the organic EL element 1 was produced.
  • a glass cover is prepared, and an epoxy-based photocurable adhesive (Luxtrac LC0629B manufactured by Toagosei Co., Ltd.) is applied as a sealant to the side edge of the glass cover.
  • the surface (cathode side) was adhered to the glass substrate of the organic EL element 1 so as to be covered with a glass cover.
  • UV light was irradiated from the glass substrate side of the organic EL element 1 to cure the adhesive, and the organic EL element 1 was sealed with a glass cover.
  • the organic EL element 1 after the sealing was designated as “Sample 1”.
  • Organic EL elements 2 to 4 were prepared in the same manner except that the host compound was changed to the compounds shown in Table 2 in preparation of the organic EL element 1. Samples 2 to 4 were used.
  • Organic EL element 5 was prepared in the same manner as Sample 5 except that the structure of the light-emitting layer was changed as described below.
  • a heating boat containing a-11, Ir-1, and Ir-6 was energized and heated, and the deposition rates were 0.1 nm / second, 0.0001 nm / second, and 0.0002 nm / second, respectively. And co-evaporated on the hole transport layer to provide a first light-emitting layer having a thickness of 20 nm.
  • a heating boat containing a-9 and DP-1 is energized and heated on the first light emitting layer, and the first light emitting layer is coated on the first light emitting layer at a deposition rate of 0.1 nm / second and 0.02 nm / second, respectively.
  • the second light emitting layer having a thickness of 20 nm was provided by vapor deposition.
  • each film thickness of the said 1st light emitting layer and the 2nd light emitting layer was vapor-deposited so that the total film thickness as the whole light emitting layer might be 40 nm.
  • Organic EL element 6 was prepared in the same manner as Sample 6 except that the structure of the light emitting layer was changed as follows in the preparation of organic EL element 1.
  • a heating boat containing a-9 and DP-1 is energized and heated, and co-deposited on the hole transport layer at a deposition rate of 0.1 nm / second and 0.02 nm / second, respectively.
  • a first light emitting layer having a thickness of 20 nm was provided.
  • the first light emitting layer was heated by energizing a heating boat containing a-11, Ir-1, and Ir-6, and the deposition rates were 0.1 nm / second, 0.0001 nm / second, and 0.0002 nm, respectively.
  • / Second was co-evaporated on the first light emitting layer, and a second light emitting layer having a thickness of 20 nm was provided.
  • each film thickness of the said 1st light emitting layer and the 2nd light emitting layer was vapor-deposited so that the total film thickness as the whole light emitting layer might be 40 nm.
  • a heating boat containing a-11, Ir-1, and Ir-6 was energized and heated, and the deposition rates were 0.1 nm / second, 0.0001 nm / second, and 0.0002 nm / second, respectively. And co-evaporated on the hole transport layer to provide a first light emitting layer having a thickness of 13.3 nm.
  • a heating boat containing a-9 and DP-1 is energized and heated on the first light emitting layer, and the first light emitting layer is coated on the first light emitting layer at a deposition rate of 0.1 nm / second and 0.02 nm / second, respectively.
  • the 2nd light emitting layer It vapor-deposited and provided the 2nd light emitting layer with a film thickness of 13.4 nm. Further, the second light emitting layer was heated by energizing a heating boat containing a-9, DP-1, and Ir-6, and the deposition rates were 0.1 nm / second, 0.02 nm / second, and 0.0002 nm, respectively. / Second was co-evaporated on the second light emitting layer, and a third light emitting layer having a thickness of 13.3 nm was provided. In addition, each film thickness of the said 1st light emitting layer, the 2nd light emitting layer, and the 3rd light emitting layer was vapor-deposited so that the total film thickness as a whole light emitting layer might be 40 nm.
  • Organic EL elements 8 to 10 In the preparation of organic EL element 5, the compounds shown in Table 2 are used as constituent materials for the host compound, the blue dopant, and the electron transport layer adjacent to the cathode side of the light emitting layer. Organic EL elements 8 to 10 were produced in the same manner except that the samples were changed to Samples 8 to 10.
  • ⁇ EL 1 ⁇ [EL (after driving) / EL (before driving)]
  • ⁇ PL 1 ⁇ [PL (after driving) / PL (before driving)]
  • USB spectrum manufactured by Ocean Optics
  • PL spectrum measurement was used for PL spectrum measurement, and the spectrum measurement was performed under conditions of room temperature (23 ° C.) and excitation wavelength of 365 nm.
  • the spectrum measurement after the drive was performed within 2 hours from that time after the EL was driven until the initial luminance became about half. Thereafter, the ratio of each value between ⁇ PL and ⁇ EL ( ⁇ PL / ⁇ EL) was calculated. Table 2 shows the calculation results.
  • region was represented by the relative value which sets the light emission area of the sample 1 to 100.
  • the organic EL elements 3 to 10 of the present invention are not compared with the organic EL elements 1 and 2 of the comparative example in terms of driving voltage, light emitting region, light emission efficiency, and light emission lifetime.
  • the light emitting layer contains a host compound and a heterodopant, and the relationship between the LUMO (H) level of the host compound of the light emitting layer and the lowest LUMO (L min ) level among the ligands of the dopant, the coordination It is possible to define the relationship between the LUMO (L min ) level of the child, the LUMO (C) level of the constituent material of the cathode side adjacent layer of the light emitting layer, and the LUMO (H) level of the host compound of the light emitting layer. It turns out that it is useful for providing the organic EL element which does not raise
  • the present invention can be particularly suitably used for providing an organic EL device that does not increase in voltage and has excellent luminous efficiency and luminous lifetime.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un élément électroluminescent organique, caractérisé en ce qu'il comprend au moins une couche émettrice de lumière contenant un composé hôte et un dopant qui est représenté par la formule structurale L1L2L3M (dans laquelle chaque L des L1 à L3 représente un ligand bidenté et M représente un métal central). Cet élément électroluminescent organique est en outre caractérisé en ce qu'au moins deux ligands choisis arbitrairement à partir des ligands L1 à L3 du dopant sont différents l'un de l'autre ; et en ce que le niveau LUMO (H) du composé hôte de la couche émettrice de lumière, le plus bas niveau LUMO (Lmin) des ligands L1 à L3 du dopant, et le niveau LUMO (C) du matériau constituant de la couche adjacente côté électrode négative de la couche émettrice de lumière, satisfont les expressions conditionnelles (i) et (ii) : 0 < LUMO (Lmin) - LUMO (H) ≤ 0,5eV (i) LUMO (H) - 0,5eV < LUMO (C) < LUMO (Lmin) (ii)
PCT/JP2013/058659 2012-04-03 2013-03-26 Élément électroluminescent organique WO2013150909A1 (fr)

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US10941171B2 (en) 2017-11-22 2021-03-09 Samsung Electronics Co., Ltd. Organometallic compound and organic light-emitting device including the same
US11251375B2 (en) 2018-11-20 2022-02-15 Canon Kabushiki Kaisha While organic EL element

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KR101837095B1 (ko) * 2009-10-28 2018-03-09 바스프 에스이 이종 리간드 카르벤 착체 및 유기 전자장치에서의 이의 용도
JP5649327B2 (ja) * 2010-04-22 2015-01-07 ユー・ディー・シー アイルランド リミテッド 有機電界発光素子
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JP2009510796A (ja) * 2005-10-04 2009-03-12 ユニバーサル ディスプレイ コーポレイション 高効率リン光有機発光デバイスのための電子妨害層
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10941171B2 (en) 2017-11-22 2021-03-09 Samsung Electronics Co., Ltd. Organometallic compound and organic light-emitting device including the same
US11251375B2 (en) 2018-11-20 2022-02-15 Canon Kabushiki Kaisha While organic EL element

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