WO2016051977A1 - 有機電界発光素子用材料及びこれを用いた有機電界発光素子 - Google Patents
有機電界発光素子用材料及びこれを用いた有機電界発光素子 Download PDFInfo
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- WO2016051977A1 WO2016051977A1 PCT/JP2015/073155 JP2015073155W WO2016051977A1 WO 2016051977 A1 WO2016051977 A1 WO 2016051977A1 JP 2015073155 W JP2015073155 W JP 2015073155W WO 2016051977 A1 WO2016051977 A1 WO 2016051977A1
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- Prior art keywords
- light emitting
- organic electroluminescent
- organic
- electroluminescent device
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- 239000000463 material Substances 0.000 title claims abstract description 139
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 37
- 125000003118 aryl group Chemical group 0.000 claims abstract description 36
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- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 21
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- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
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- 125000001424 substituent group Chemical group 0.000 description 4
- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical class N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 3
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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Definitions
- the present invention relates to an organic electroluminescent device using a specific heterocyclic compound as a material for an organic electroluminescent device, and more particularly to a thin film device that emits light by applying an electric field to a light emitting layer containing the organic compound. It is.
- an organic electroluminescent element (hereinafter referred to as an organic EL element) is composed of a light emitting layer and a pair of counter electrodes sandwiching the layer as the simplest structure. That is, in an organic EL element, when an electric field is applied between both electrodes, electrons are injected from the cathode, holes are injected from the anode, and these are recombined in the light emitting layer to emit light. .
- the type of electrode is optimized for the purpose of improving the efficiency of carrier injection from the electrode, and the light emission consists of a hole transport layer made of aromatic diamine and 8-hydroxyquinoline aluminum complex (Alq 3 ).
- Alq 3 8-hydroxyquinoline aluminum complex
- CBP 4,4′-bis (9-carbazolyl) biphenyl
- Ir (ppy) 3 2,4′-bis (9-carbazolyl) biphenyl
- a host material having high triplet excitation energy and balanced in both charge (hole / electron) injection and transport characteristics is required. Further, a compound that is electrochemically stable and has high heat resistance and excellent amorphous stability is desired, and further improvement is required.
- H-2 a heterocyclic compound represented by the following formula.
- This compound has a structural feature having an amino group directly on the carbon atom of the basic skeleton or via a linking group. Therefore, the transportability and stability with respect to electrons deteriorate, and a practically sufficient organic EL device is obtained. The problem is that characteristics cannot be obtained.
- An object of this invention is to provide the practically useful organic EL element which has high efficiency and high drive stability in view of the said present condition, and a compound suitable for it.
- the present invention is an organic electroluminescent element material comprising a heterocyclic compound represented by the general formula (1).
- R 1 is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted carbon group having 3 to 22 represents an aromatic heterocyclic group, or a substituted or unsubstituted linked aromatic group in which these aromatic rings are linked by 2-6.
- R 2 to R 5 are independently an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, oxygen or sulfur as a hetero atom Or a substituted or unsubstituted aromatic heterocyclic group having 3 to 22 carbon atoms, or a substituted or unsubstituted linked aromatic group formed by connecting these aromatic rings in an amount of 2 to 6; a, b, c, and d each independently represents an integer of 0-2.
- the present invention provides an organic electroluminescence device material in which an anode, an organic layer and a cathode are laminated on a substrate, wherein at least one of the organic layers is represented by the general formula (1) It is an organic electroluminescent element characterized by being an organic layer containing.
- the organic layer containing the organic electroluminescent element material is preferably at least one layer selected from the group consisting of a light emitting layer, an electron transport layer, and a hole blocking layer, and more preferably a light emitting layer.
- the luminescent layer containing an organic electroluminescent element material is a luminescent layer
- the luminescent layer preferably contains a host material and a luminescent dopant
- the organic electroluminescent element material can be used as a host material or a luminescent dopant. Is also applicable. Two or more types of host materials may be included in the light emitting layer, and one or more types of light emitting dopants may be used, and the organic electroluminescent element material is applied as at least one type of host material or light emitting dopant. it can.
- organic electroluminescent element material is a host material
- a phosphorescent light emitting dopant, a fluorescent light emitting dopant, or a delayed fluorescent light emitting dopant is applicable as the light emitting dopant.
- the organic electroluminescent element material when it is a light emitting dopant, it can be applied as a fluorescent light emitting dopant or a delayed fluorescent light emitting dopant.
- the organic electroluminescent device material of the present invention exhibits excellent electron injection transportability and hole injection transportability, and has appropriate minimum singlet excitation energy and minimum triplet excitation energy that affect the light emission characteristics. Can be used in an organic EL device to reduce the driving voltage of the device and achieve high luminous efficiency. In addition, since the organic electroluminescent element material exhibits good amorphous characteristics and high thermal stability and electrical stability, the organic EL element using the organic electroluminescent element has a long driving life and a practical level of durability. .
- the organic electroluminescent element material of the present invention is a heterocyclic compound represented by the general formula (1).
- R 1 is an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted group.
- An aromatic heterocyclic group having 3 to 22 carbon atoms, or an aromatic ring thereof (the above substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic group having 3 to 22 carbon atoms); Represents a substituted or unsubstituted linked aromatic group formed by connecting 2 to 6 heterocyclic groups.
- a substituted or unsubstituted aromatic hydrocarbon group having 6 to 22 carbon atoms a substituted or unsubstituted aromatic heterocyclic group having 3 to 16 carbon atoms, or 2 to 6 linked aromatic rings thereof.
- a substituted or unsubstituted linked aromatic group a substituted or unsubstituted aromatic hydrocarbon group having 6 to 22 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 16 carbon atoms, or 2 to 6 linked aromatic rings thereof.
- R 2 to R 5 are each independently an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, oxygen as a hetero atom, or It represents a substituted or unsubstituted aromatic heterocyclic group having 3 to 22 carbon atoms containing only sulfur, or a substituted or unsubstituted linked aromatic group formed by connecting these aromatic rings in 2 to 6 parts.
- the aromatic hydrocarbon group having 6 to 22 carbon atoms a substituted or unsubstituted aromatic heterocyclic group having 3 to 16 carbon atoms containing only oxygen or sulfur as a hetero atom, or 2 to It is a substituted or unsubstituted linked aromatic group formed by 6 linkages.
- a, b, c, and d each independently represents an integer of 0-2.
- R 1 to R 5 specific examples of the unsubstituted aromatic hydrocarbon group include aromatic hydrocarbon compounds such as benzene, naphthalene, fluorene, anthracene, phenanthrene, triphenylene, tetraphenylene, fluoranthene, pyrene, and chrysene. And a group formed by removing hydrogen from benzene, naphthalene, fluorene, phenanthrene, or triphenylene.
- aromatic hydrocarbon compounds such as benzene, naphthalene, fluorene, anthracene, phenanthrene, triphenylene, tetraphenylene, fluoranthene, pyrene, and chrysene.
- a group formed by removing hydrogen from benzene, naphthalene, fluorene, phenanthrene, or triphenylene such as benzene, naphthalene, fluorene, an
- unsubstituted aromatic heterocyclic group examples include pyridine, pyrimidine, triazine, quinoline, isoquinoline, quinoxaline, quinazoline, naphthyridine, carbazole, acridine, azepine, tribenzoazepine, phenazine, phenoxazine, phenothiazine, dibenzophosphole.
- Dibenzoborol, dibenzofuran, dibenzothiophene, dibenzodioxin, thianthrene and other aromatic heterocyclic compounds such as groups formed by removing hydrogen, preferably pyridine, pyrimidine, triazine, carbazole, dibenzofuran, dibenzothiophene It is a group that occurs.
- the aromatic heterocyclic compound is a group formed by removing hydrogen from an aromatic heterocyclic compound containing only oxygen or sulfur as a hetero atom, and constitutes a heterocyclic ring. Groups derived from aromatic heterocyclic compounds containing atoms other than oxygen or sulfur as heteroatoms are excluded.
- the unsubstituted linking aromatic group includes a plurality of aromatic rings of the aromatic hydrocarbon compound or aromatic heterocyclic compound described in the above-mentioned unsubstituted aromatic hydrocarbon group and unsubstituted aromatic heterocyclic group with a single bond.
- the linked aromatic group is a group formed by connecting 2 to 6 aromatic rings, and the aromatic rings to be connected may be the same or different, and an aromatic hydrocarbon group and an aromatic heterocyclic group Both may be included.
- the number of aromatic rings to be connected is preferably 2 to 4, more preferably 2 or 3. *
- connection aromatic group is represented by a following formula, for example.
- Ar 1 to Ar 5 represent a substituted or unsubstituted aromatic ring
- linked aromatic groups include biphenyl, terphenyl, phenylnaphthalene, diphenylnaphthalene, phenylanthracene, diphenylanthracene, diphenylfluorene, bipyridine, bipyrimidine, vitriazine, biscarbazole, phenylpyridine, phenylpyrimidine, phenyltriazine, phenylcarbazole , Groups generated by removing hydrogen from diphenylpyridine, diphenyltriazine, biscarbazolylbenzene, phenyldibenzofuran, phenyldibenzothiophene, and the like.
- the aromatic hydrocarbon group, aromatic heterocyclic group or linked aromatic group may have a substituent, and when it has a substituent, preferred substituents include alkyl groups having 1 to 12 carbon atoms, carbon An alkoxy group having 1 to 12 carbon atoms or an acyl group having 2 to 13 carbon atoms. More preferably, it is an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 2 carbon atoms, or an acetyl group.
- a, b, c, and d represent an integer of 0-2.
- (a + b + c + d) is an integer of 0 to 4, more preferably 0 to 2.
- the heterocyclic compound represented by the general formula (1) can be synthesized, for example, by the method shown in the following reaction formula.
- heterocyclic compound represented by the general formula (1) Specific examples of the heterocyclic compound represented by the general formula (1) are shown below, but the organic electroluminescent element material of the present invention is not limited thereto.
- the organic electroluminescent element material of the present invention comprises a heterocyclic compound represented by the general formula (1).
- An excellent organic electroluminescence device can be obtained by incorporating the material for an organic electroluminescence device of the present invention into at least one organic layer of an organic EL device in which an anode, a plurality of organic layers and a cathode are laminated on a substrate. give.
- As the organic layer to be contained a light emitting layer, an electron transport layer or a hole blocking layer is suitable.
- the organic electroluminescent element material of the present invention when used in the light emitting layer, it can be used as a host material of a light emitting layer containing a dopant for fluorescent light emission, delayed fluorescent light emission or phosphorescent light emission, and the organic electroluminescent element material of the present invention can be used for fluorescent light and It can be used as an organic light emitting material that emits delayed fluorescence.
- organic light-emitting material that emits fluorescence and delayed fluorescence other organic compounds in which at least one of excited singlet energy and excited triplet energy has a higher value than the organic electroluminescent element material of the present invention are used. It is preferable to use it as a host material.
- the organic electroluminescent element material of the present invention is particularly preferably contained as a host material of a light emitting layer containing a phosphorescent dopant.
- the organic EL device of the present invention has an organic layer having at least one light emitting layer between an anode and a cathode laminated on a substrate, and the at least one organic layer is for the organic electroluminescent device of the present invention.
- the organic electroluminescent device material of the present invention is included in the light emitting layer together with a phosphorescent dopant.
- the structure of the organic EL element of the present invention will be described with reference to the drawings.
- the structure of the organic EL element of the present invention is not limited to the illustrated one.
- FIG. 1 is a cross-sectional view showing a structural example of a general organic EL device used in the present invention, wherein 1 is a substrate, 2 is an anode, 3 is a hole injection layer, 4 is a hole transport layer, and 5 is a light emitting layer. , 6 represents an electron transport layer, and 7 represents a cathode.
- the organic EL device of the present invention may have an exciton blocking layer adjacent to the light emitting layer, and may have an electron blocking layer between the light emitting layer and the hole injection layer.
- the exciton blocking layer can be inserted on either the anode side or the cathode side of the light emitting layer, or both can be inserted simultaneously.
- the organic EL device of the present invention has a substrate, an anode, a light emitting layer and a cathode as essential layers, but it is preferable to have a hole injecting and transporting layer and an electron injecting and transporting layer in layers other than the essential layers, and further emit light. It is preferable to have a hole blocking layer between the layer and the electron injecting and transporting layer.
- the hole injection / transport layer means either or both of a hole injection layer and a hole transport layer
- the electron injection / transport layer means either or both of an electron injection layer and an electron transport layer.
- the organic EL element of the present invention is preferably supported on a substrate.
- the substrate is not particularly limited as long as it is conventionally used for an organic EL element.
- a substrate made of glass, transparent plastic, quartz, or the like can be used.
- an electrode material made of a metal, an alloy, an electrically conductive compound, or a mixture thereof having a high work function (4 eV or more) is preferably used.
- electrode materials 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.
- these electrode materials may be formed into a thin film by a method such as vapor deposition or sputtering, and a pattern having a desired shape may be formed by a photolithography method, or when the pattern accuracy is not required (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 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.
- an electron injecting metal a material having a low work function (4 eV or less) metal
- an alloy a material having a low work function (4 eV or less) metal
- an alloy a material having a low work function (4 eV or less) metal
- an alloy referred to as an electron injecting metal
- an alloy referred to as an electron injecting metal
- 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 the 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 to 200 nm.
- the light emission luminance is improved, which is convenient.
- 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 above metal with a predetermined film thickness.
- an element in which both the anode and the cathode are transmissive can be manufactured.
- the light emitting layer is a layer that emits light after excitons are generated by recombination of holes and electrons injected from the anode and the cathode, respectively, and the light emitting layer may contain an organic light emitting material and a host material. Good.
- the organic light emitting material include a fluorescent light emitting material (fluorescent light emitting dopant), a phosphorescent light emitting material (phosphorescent light emitting dopant), and a delayed fluorescent light emitting material (delayed fluorescent light emitting dopant).
- the fluorescent light emitting material may be at least one kind of fluorescent light emitting material, but it is preferable to use the fluorescent light emitting material as a fluorescent light emitting dopant and include a host material.
- the organic EL device material of the present invention (also referred to as the heterocyclic compound of the present invention) can be used, but since it is known from many patent documents and the like, it can be selected from them. it can.
- Polyphenylene, polyphenylene vinylene polymer compounds such as, organic silane derivatives, and the like.
- Preferred examples include condensed aromatic compounds, styryl compounds, diketopyrrolopyrrole compounds, oxazine compounds, pyromethene metal complexes, transition metal complexes, and lanthanoid complexes, more preferably naphthacene, pyrene, chrysene, triphenylene, benzo [c] phenanthrene, Benzo [a] anthracene, pentacene, perylene, fluoranthene, acenaphthofluoranthene, dibenzo [a, j] anthracene, dibenzo [a, h] anthracene, benzo [a] naphthacene, hexacene, anthanthrene, naphtho [2,1 -f] isoquinoline, ⁇ -naphtha
- the heterocyclic compound of the present invention can be used, but since it is known from many patent documents and the like, it can be selected from them.
- a compound having a condensed aryl ring such as naphthalene, anthracene, phenanthrene, pyrene, chrysene, naphthacene, triphenylene, perylene, fluoranthene, fluorene, indene or a derivative thereof, N, N′-dinaphthyl-N, N′-diphenyl-4
- Aromatic amine derivatives such as 4,4'-diphenyl-1,1'-diamine
- metal chelated oxinoid compounds such as tris (8-quinolinato) aluminum (III)
- bisstyryl derivatives such as distyrylbenzene derivatives, tetraphenyl Butadiene derivatives, indene derivatives, coumarin derivatives, oxadiazole derivatives, pyrrolopyr
- the amount of the fluorescent light emitting dopant contained in the light emitting layer is 0.01 to 20% by weight, preferably 0.1 to 10% by weight. It should be in range.
- an organic EL element injects electric charges into a luminescent material from both an anode and a cathode, generates an excited luminescent material, and emits light.
- a charge injection type organic EL device it is said that 25% of the generated excitons are excited to a singlet excited state and the remaining 75% are excited to a triplet excited state.
- certain fluorescent materials emit triplet-triplet annihilation or heat after energy transition to triplet excited state due to intersystem crossing etc. It is known that, due to the absorption of energy, the singlet excited state is crossed back to back and emits fluorescence, thereby expressing thermally activated delayed fluorescence.
- the organic EL device of the present invention can also exhibit delayed fluorescence. In this case, both fluorescence emission and delayed fluorescence emission can be included. However, light emission from the host material may be partly or partly emitted.
- the delayed light emitting material may use at least one delayed light emitting material alone, but the delayed fluorescent material may be used as a delayed fluorescent light emitting dopant and include a host material. preferable.
- the heterocyclic compound of the present invention can be used, but it can also be selected from known delayed fluorescence materials.
- a tin complex, an indolocarbazole derivative, a copper complex, a carbazole derivative, and the like can be given. Specific examples include compounds described in the following non-patent documents and patent documents, but are not limited to these compounds.
- delayed luminescent materials are shown, but are not limited to the following compounds.
- the amount of the delayed fluorescent material contained in the light emitting layer is 0.01 to 50% by weight, preferably 0.1 to 20%. It may be in the range of wt%, more preferably in the range of 0.01 to 10 wt%.
- the heterocyclic compound of the present invention can be used, but it can also be selected from other compounds.
- a compound having a condensed aryl ring such as naphthalene, anthracene, phenanthrene, pyrene, chrysene, naphthacene, triphenylene, perylene, fluoranthene, fluorene, indene or a derivative thereof, N, N′-dinaphthyl-N, N′-diphenyl-4
- Aromatic amine derivatives such as 4,4'-diphenyl-1,1'-diamine, metal chelated oxinoid compounds such as tris (8-quinolinato) aluminum (III), bisstyryl derivatives such as distyrylbenzene derivatives, tetraphenyl Butadiene derivatives, indene derivatives, coumarin derivatives, oxadiazole derivatives, pyrrolopyridine derivatives, perinone derivatives
- the light emitting layer When the light emitting layer is a phosphorescent light emitting layer, the light emitting layer contains a phosphorescent light emitting dopant and a host material.
- the phosphorescent dopant material preferably contains an organometallic complex containing at least one metal selected from ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum and gold.
- Preferable phosphorescent dopants include complexes such as Ir (ppy) 3 having a noble metal element of Ir such as the central metal, Ir (bt) complexes such as 2 ⁇ acac 3, complexes such as PtOEt 3 and the like. Specific examples of these complexes are shown below, but are not limited to the following compounds.
- the amount of the phosphorescent dopant contained in the light emitting layer is 2 to 40% by weight, preferably 3 to 20% by weight.
- the light emitting layer is a phosphorescent light emitting layer
- the heterocyclic compound of the present invention is used as the host material in the light emitting layer.
- the material used for the light emitting layer may be another host material.
- a plurality of known host materials may be used in combination.
- the known host compound that can be used is preferably a compound that has a hole transporting ability and an electron transporting ability, prevents the emission of longer wavelengths, and has a high glass transition temperature.
- host materials are known from a large number of patent documents, and can be selected from them.
- specific examples of the host material include, but are not limited to, indole derivatives, carbazole derivatives, dicarbazole derivatives, indolocarbazole derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives.
- the light emitting layer may be any one of a fluorescent light emitting layer, a delayed fluorescent light emitting layer and a phosphorescent light emitting layer, but is preferably a phosphorescent light emitting layer.
- the injection layer is a layer provided between the electrode and the organic layer for lowering the driving voltage and improving the luminance of light emission.
- the injection layer can be provided as necessary.
- 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.
- the heterocyclic compound of the present invention for the hole blocking layer, but when this heterocyclic compound is used for any other organic layer, a known hole blocking layer material may be used. Moreover, as a hole-blocking layer material, the material of the electron carrying layer mentioned later can be used as needed.
- the electron blocking layer is made of a material that has a function of transporting holes and has a very small ability to transport electrons.
- the electron blocking layer blocks the electrons while transporting holes, and the probability of recombination of electrons and holes. Can be improved.
- the material for the electron blocking layer As the material for the electron blocking layer, the material for the hole transport layer described later can be used as necessary.
- the thickness of the electron blocking layer is preferably 3 to 100 nm, more preferably 5 to 30 nm.
- the exciton blocking layer is a layer that prevents excitons generated by recombination of holes and electrons in the light emitting layer from diffusing into the charge transport layer, and is excited by the insertion of the exciton blocking layer. It is possible to efficiently confine the child in the light emitting layer, and the light emission efficiency of the device can be improved.
- the exciton blocking layer can be inserted on either the anode side or the cathode side adjacent to the light emitting layer, or both can be inserted simultaneously.
- the heterocyclic compound of the present invention can be used as the material for the exciton blocking layer.
- the heterocyclic compound of the present invention can be used.
- other materials for example, 1,3-dicarbazolylbenzene (mCP), bis (2-methyl-8) -Quinolinolato) -4-phenylphenolato aluminum (III) (BAlq).
- the hole transport layer is made of a hole transport material having a function of transporting holes, and the hole transport layer can be provided as a single layer or a plurality of layers.
- the hole transport material has either hole injection or transport or electron barrier properties, and may be either organic or inorganic.
- the known hole transporting material that can be used it is preferable to use the organic electroluminescent element material of the present invention, but any one of conventionally known compounds can be selected and used.
- Known hole transporting materials that can be used include, for example, 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, stilbene derivatives, silazane derivatives, aniline copolymers, conductive polymer oligomers, thiophene oligomers, porphyrin compounds, aromatic tertiary amine compounds, carbazole derivatives and styrylamine compounds
- the electron transport layer is made of a material having a function of transporting electrons, and the electron transport layer can be provided as a single layer or a plurality of layers.
- an electron transport material which may also serve as a hole blocking material
- the heterocyclic compound of the present invention for the electron transport layer, any one of conventionally known compounds can be selected and used.
- nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiols examples include pyran dioxide derivatives, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, oxadiazole derivatives, and the like.
- a thiadiazole derivative in which the oxygen atom of the oxadiazole ring is substituted with a sulfur atom, and 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.
- dibenofen (1-A) (109 mmol, 20.0 kg) and dehydrated THF (100 mL) were added to a 1000 mL reactor and stirred at 0 ° C. for 30 minutes.
- 2N BuLi-hexane solution (60 mL, 156 mmol) was added dropwise. After completion of the dropwise addition, the mixture was heated to reflux for 6 hours. After cooling to room temperature, dehydrated DMF (20 mL, 160 mmol) was added dropwise, and the mixture was stirred overnight at room temperature.
- the reaction mixture was poured into 6N hydrochloric acid (500 mL), extracted with acetic acid, and the organic layer was washed with water and dried. 8.0 g of compound (1-B) was obtained by column chromatography.
- reaction mixture was poured into 2N aqueous sodium hydroxide solution, washed with ethyl acetate, and the ethyl acetate layer was extracted with 2N aqueous sodium hydroxide solution.
- the aqueous layers were combined, adjusted to pH 1 by adding 6N hydrochloric acid, and extracted with ethyl acetate.
- the organic layer was washed with water and the solvent was distilled off to obtain 9.6 g of compound (1-E).
- Example 2 Each thin film was laminated at a vacuum degree of 2.0 ⁇ 10 ⁇ 5 Pa by a vacuum deposition method on a glass substrate on which an anode made of indium tin oxide (ITO) having a thickness of 150 nm was formed.
- ITO indium tin oxide
- CuPC copper phthalocyanine
- ⁇ -NPD was formed to a thickness of 40 nm as a hole transport layer.
- the compound (3) as the host material of the light emitting layer and Ir (ppy) 3 as the dopant are co-evaporated from different evaporation sources to form a light emitting layer with a thickness of 35 nm. did.
- the concentration of Ir (ppy) 3 was 7.0%.
- Alq 3 was formed to a thickness of 40 nm as an electron transport layer.
- lithium fluoride (LiF) was formed to a thickness of 0.5 nm as an electron injection layer on the electron transport layer.
- Al was formed as an electrode to a thickness of 170 nm to produce an organic EL device.
- the organic EL element had light emission characteristics as shown in Table 1.
- Table 1 the luminance, voltage, and luminous efficiency show values (initial characteristics) when driven at 10 mA / cm 2 .
- the maximum wavelength of the device emission spectrum was 520 nm, indicating that light emission from Ir (ppy) 3 was obtained.
- Examples 3-7 As in Example 2, except that the compound (4), (5), (10), (13) or (18) was used as the host material of the light emitting layer in Example 2 instead of the compound (3). Thus, an organic EL element was produced.
- Example 8 Organic EL as in Example 2 except that the compound (3) and CBP were co-deposited at a ratio of 30 to 70 (weight ratio) instead of the compound (3) as the host material of the light emitting layer in Example 2. A device was created.
- Example 9 An organic EL device was produced in the same manner as in Example 2 except that instead of compound (3), compound (3) and CBP were co-deposited at a ratio of 40:60 as the host material of the light emitting layer in Example 2. .
- Example 10 An organic EL device was prepared in the same manner as in Example 2 except that instead of compound (3), compound (18) and compound (5) were co-deposited at a ratio of 40:60 as the host material of the light emitting layer in Example 2. It was created.
- Example 11 An organic EL device was prepared in the same manner as in Example 2 except that instead of compound (3), compound (18) and compound (5) were co-evaporated at a ratio of 50:50 as the host material of the light emitting layer in Example 2. It was created.
- Comparative Example 1 An organic EL device was produced in the same manner as in Example 2 except that CBP was used instead of the compound (3) as the host material of the light emitting layer in Example 2.
- Comparative Example 2 An organic EL device was produced in the same manner as in Example 2, except that the heterocyclic compound (H-1) was used in place of the compound (3) as the host material of the light emitting layer in Example 2.
- Comparative Example 3 An organic EL device was produced in the same manner as in Example 2 except that the heterocyclic compound (H-2) was used in place of the compound (3) as the host material of the light emitting layer in Example 2.
- the organic EL devices obtained in Examples 3 to 11 and Comparative Examples 1 to 3 were evaluated in the same manner as in Example 2. As a result, it was confirmed that they had the light emission characteristics as shown in Table 1.
- the maximum wavelength of the emission spectra of the organic EL devices obtained in Examples 3 to 11 and Comparative Examples 1 to 3 was 530 nm, and it was identified that light emission from Ir (ppy) 3 was obtained.
- the organic electroluminescent element material of the present invention can be used for an organic EL element, it can achieve a reduction in driving voltage and high luminous efficiency, a long driving life, and durability at a practical level. It can utilize suitably for thin film type display devices, such as a flat panel display.
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Abstract
Description
また、この有機電界発光素子用材料は、良好なアモルファス特性ならびに高い熱安定性および電気的安定性を示すことから、これを用いた有機EL素子は駆動寿命が長く、実用レベルの耐久性を有する。
本発明の有機EL素子は、基板に支持されていることが好ましい。この基板については、特に制限はなく、従来から有機EL素子に慣用されているものであればよく、例えば、ガラス、透明プラスチック、石英などからなるものを用いることができる。
有機EL素子における陽極としては、仕事関数の大きい(4eV以上)金属、合金、電気伝導性化合物及びこれらの混合物を電極物質とするものが好ましく用いられる。このような電極物質の具体例としては、Au等の金属、CuI、インジウムチンオキシド(ITO)、SnO2、ZnO等の導電性透明材料が挙げられる。また、IDIXO(In2O3-ZnO)等非晶質で透明導電膜を作製可能な材料を用いてもよい。陽極はこれらの電極物質を蒸着やスパッタリング等の方法により、薄膜を形成させ、フォトリソグラフィー法で所望の形状のパターンを形成してもよく、あるいはパターン精度をあまり必要としない場合は(100μm以上程度)、上記電極物質の蒸着やスパッタリング時に所望の形状のマスクを介してパターンを形成してもよい。あるいは、有機導電性化合物のように塗布可能な物質を用いる場合には、印刷方式、コーティング方式等湿式成膜法を用いることもできる。この陽極より発光を取り出す場合には、透過率を10%より大きくすることが望ましく、また陽極としてのシート抵抗は数百Ω/□以下が好ましい。更に膜厚は材料にもよるが、通常10~1000nm、好ましくは10~200nmの範囲で選ばれる。
一方、陰極としては、仕事関数の小さい(4eV以下)金属(電子注入性金属と称する)、合金、電気伝導性化合物及びこれらの混合物を電極物質とするものが用いられる。このような電極物質の具体例としては、ナトリウム、ナトリウム-カリウム合金、マグネシウム、リチウム、マグネシウム/銅混合物、マグネシウム/銀混合物、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム(Al2O3)混合物、インジウム、リチウム/アルミニウム混合物、希土類金属等が挙げられる。これらの中で、電子注入性及び酸化等に対する耐久性の点から、電子注入性金属とこれより仕事関数の値が大きく安定な金属である第二金属との混合物、例えば、マグネシウム/銀混合物、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム(Al2O3)混合物、リチウム/アルミニウム混合物、アルミニウム等が好適である。陰極はこれらの電極物質を蒸着やスパッタリング等の方法により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、陰極としてのシート抵抗は数百Ω/□以下が好ましく、膜厚は通常10nm~5μm、好ましくは50~200nmの範囲で選ばれる。なお、発光した光を透過させるため、有機EL素子の陽極又は陰極のいずれか一方が、透明又は半透明であれば発光輝度が向上し好都合である。
発光層は、陽極及び陰極のそれぞれから注入された正孔及び電子が再結合することにより励起子が生成した後、発光する層であり、発光層には有機発光材料とホスト材料を含むことがよい。有機発光材料(発光ドーパント)としては、蛍光発光材料(蛍光発光ドーパント)、燐光発光材料(燐光発光ドーパント)及び遅延蛍光発光材料(遅延蛍光発光ドーパント)が挙げられる。
注入層とは、駆動電圧低下や発光輝度向上のために電極と有機層間に設けられる層のことで、正孔注入層と電子注入層があり、陽極と発光層又は正孔輸送層の間、及び陰極と発光層又は電子輸送層との間に存在させてもよい。注入層は必要に応じて設けることができる。
正孔阻止層とは、広い意味では電子輸送層の機能を有し、電子を輸送する機能を有しつつ正孔を輸送する能力が著しく小さい正孔阻止材料からなり、電子を輸送しつつ正孔を阻止することで電子と正孔の再結合確率を向上させることができる。
電子阻止層とは、正孔を輸送する機能を有しつつ電子を輸送する能力が著しく小さい材料から成り、正孔を輸送しつつ電子を阻止することで電子と正孔が再結合する確率を向上させることができる。
励起子阻止層とは、発光層内で正孔と電子が再結合することにより生じた励起子が電荷輸送層に拡散することを阻止するための層であり、励起子阻止層の挿入により励起子を効率的に発光層内に閉じ込めることが可能となり、素子の発光効率を向上させることができる。励起子阻止層は発光層に隣接して陽極側、陰極側のいずれにも挿入することができ、両方同時に挿入することも可能である。
正孔輸送層とは、正孔を輸送する機能を有する正孔輸送材料からなり、正孔輸送層は単層又は複数層設けることができる。
電子輸送層とは、電子を輸送する機能を有する材料からなり、電子輸送層は単層又は複数層設けることができる。
膜厚 150nm の 酸化インジウムスズ(ITO)からなる陽極が形成されたガラス基板上に、各薄膜を真空蒸着法にて、真空度2.0×10-5 Pa で積層させた。まず、ITO 上に正孔注入層として、銅フタロシアニン(CuPC)を 20 nm の厚さに形成した。次に、正孔輸送層としてα-NPDを 40 nm の厚さに形成した。次に、正孔輸送層上に、発光層のホスト材料としての化合物(3)とドーパントとしてのIr(ppy)3とを異なる蒸着源から共蒸着し、35 nm の厚さに発光層を形成した。Ir(ppy)3の濃度は 7.0 %であった。次に、電子輸送層としてAlq3を40 nmの厚さに形成した。更に、電子輸送層上に、電子注入層としてフッ化リチウム(LiF)を0.5 nmの厚さに形成した。最後に、電子注入層上に、電極としてアルミニウム(Al)を170 nmの厚さに形成し、有機EL素子を作製した。
実施例2における発光層のホスト材料として、化合物(3)に代えて、化合物(4)、(5)、(10)、(13)又は(18)を用いた以外は実施例2と同様にして有機EL素子を作成した。
実施例2における発光層のホスト材料として、化合物(3)に代えて、化合物(3)とCBPを30対70の比率(重量比)で共蒸着した以外は実施例2と同様にして有機EL素子を作成した。
実施例2における発光層のホスト材料として、化合物(3)に代えて、化合物(3)とCBPを40対60の比率で共蒸着した以外は実施例2と同様にして有機EL素子を作成した。
実施例2における発光層のホスト材料として、化合物(3)に代えて、化合物(18)と化合物(5)を40対60の比率で共蒸着した以外は実施例2と同様にして有機EL素子を作成した。
実施例2における発光層のホスト材料として、化合物(3)に代えて、化合物(18)と化合物(5)を50対50の比率で共蒸着した以外は実施例2と同様にして有機EL素子を作成した。
実施例2における発光層のホスト材料として化合物(3)に代えて、CBPを用いた以外は実施例2と同様にして有機EL素子を作成した。
実施例2における発光層のホスト材料として化合物(3)に代えて、複素環化合物(H-1)を用いた以外は実施例2と同様にして有機EL素子を作成した。
実施例2における発光層のホスト材料として化合物(3)に代えて、複素環化合物(H-2)を用いた以外は実施例2と同様にして有機EL素子を作成した。
Claims (12)
- 一般式(1)で表される複素環化合物からなることを特徴とする有機電界発光素子用材料。
ここで、R1は炭素数1~12のアルキル基、炭素数1~12のアルコキシ基、置換若しくは未置換の炭素数6~30の芳香族炭化水素基、置換若しくは未置換の炭素数3~22の芳香族複素環基、又はこれらの芳香族環が2~6個連結してなる置換若しくは未置換の連結芳香族基を表す。
R2~R5は独立に、炭素数1~12のアルキル基、炭素数1~12のアルコキシ基、置換若しくは未置換の炭素数6~30の芳香族炭化水素基、ヘテロ原子として酸素又は硫黄のみを含む置換若しくは未置換の炭素数3~22の芳香族複素環基、又はこれらの芳香族環が2~6連結してなる置換若しくは未置換の連結芳香族基を表す。
a、b、c、dは独立に、0~2の整数を表す。 - 基板上に、陽極、有機層及び陰極が積層されてなる有機電界発光素子において、該有機層の少なくとも1層が請求項1に記載の有機電界発光素子用材料を含む有機層であることを特徴とする有機電界発光素子。
- 有機電界発光素子用材料を含む有機層が、発光層、電子輸送層、及び正孔阻止層からなる群れから選ばれる少なくとも一つの層である請求項2に記載の有機電界発光素子。
- 有機電界発光素子用材料を含む有機層が、発光層であることを特徴とする請求項2に記載の有機電界発光素子。
- 発光層が、発光ドーパントとホスト材料を含むことを特徴とする請求項4に記載の有機電界発光素子。
- 発光層がホスト材料と発光ドーパントとして燐光発光ドーパントを含み、前記有機電界発光素子用材料がホスト材料であることを特徴とする請求項5に記載の有機電界発光素子。
- 発光層がホスト材料と発光ドーパントとして蛍光発光ドーパントを含み、前記有機電界発光素子用材料がホスト材料であることを特徴とする請求項5に記載の有機電界発光素子。
- 発光層がホスト材料と発光ドーパントとして遅延蛍光発光ドーパントを含み、前記有機電界発光素子用材料がホスト材料であることを特徴とする請求項5に記載の有機電界発光素子。
- 発光層がホスト材料と発光ドーパントとして遅延蛍光発光ドーパントを含み、前記有機電界発光素子用材料が遅延蛍光発光ドーパントであることを特徴とする請求項5記載の有機電界発光素子。
- 発光層がホスト材料と発光ドーパントとして蛍光発光ドーパントを含み、前記有機電界発光素子用材料が蛍光発光ドーパントであることを特徴とする請求項5に記載の有機電界発光素子。
- 発光層が2種類以上のホスト材料と1種類以上の発光ドーパントを含み、少なくとも1種のホスト材料が前記有機電界発光素子用材料であることを特徴とする請求項5に記載の有機電界発光素子。
- 発光層が2種類以上のホスト材料と1種類以上の発光ドーパントを含み、少なくとも1種の発光ドーパントが前記有機電界発光素子用材料であることを特徴とする請求項5に記載の有機電界発光素子。
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WO2012090462A1 (ja) * | 2010-12-28 | 2012-07-05 | 出光興産株式会社 | 有機半導体材料、当該材料を含んでなる塗布液、及び有機薄膜トランジスタ |
JP2013232521A (ja) * | 2012-04-27 | 2013-11-14 | Udc Ireland Ltd | 有機電界発光素子、有機電界発光素子用材料並びに該有機電界発光素子を用いた発光装置、表示装置及び照明装置 |
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US10629820B2 (en) * | 2017-01-18 | 2020-04-21 | Universal Display Corporation | Organic electroluminescent materials and devices |
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WO2012090462A1 (ja) * | 2010-12-28 | 2012-07-05 | 出光興産株式会社 | 有機半導体材料、当該材料を含んでなる塗布液、及び有機薄膜トランジスタ |
JP2013232521A (ja) * | 2012-04-27 | 2013-11-14 | Udc Ireland Ltd | 有機電界発光素子、有機電界発光素子用材料並びに該有機電界発光素子を用いた発光装置、表示装置及び照明装置 |
JP2013234151A (ja) * | 2012-05-09 | 2013-11-21 | Idemitsu Kosan Co Ltd | 縮合多環芳香族化合物及びそれを用いた有機薄膜トランジスタ |
WO2014156773A1 (ja) * | 2013-03-29 | 2014-10-02 | 新日鉄住金化学株式会社 | 芳香族複素環化合物、その製造方法、有機半導体材料及び有機半導体デバイス |
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US20180233687A1 (en) | 2018-08-16 |
KR20170061144A (ko) | 2017-06-02 |
TWI656125B (zh) | 2019-04-11 |
CN106716667B (zh) | 2019-02-22 |
JPWO2016051977A1 (ja) | 2017-08-31 |
JP6563943B2 (ja) | 2019-08-21 |
KR102398991B1 (ko) | 2022-05-17 |
TW201612184A (en) | 2016-04-01 |
CN106716667A (zh) | 2017-05-24 |
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