WO2020203202A1 - 有機電界発光素子 - Google Patents
有機電界発光素子 Download PDFInfo
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- WO2020203202A1 WO2020203202A1 PCT/JP2020/011317 JP2020011317W WO2020203202A1 WO 2020203202 A1 WO2020203202 A1 WO 2020203202A1 JP 2020011317 W JP2020011317 W JP 2020011317W WO 2020203202 A1 WO2020203202 A1 WO 2020203202A1
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- host
- light emitting
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- organic
- organic electroluminescent
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- 239000000463 material Substances 0.000 claims abstract description 62
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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Definitions
- the present invention relates to an organic electroluminescent device (referred to as an organic EL device). More specifically, the present invention relates to a first host and a second host, and an organic EL device having a light emitting layer containing a light emitting dopant material.
- the phosphorescent type organic EL element that uses light emission by triplet excitons can increase the internal quantum efficiency to 100% when intersystem crossing is efficiently performed from the singlet excitons. Has been done. However, extending the life of a phosphorescent organic EL device has become a technical issue.
- Patent Document 1 discloses an organic EL device using a TTF (Triplet-Triplet Fusion) mechanism, which is one of the delayed fluorescence mechanisms.
- TTF Triplet-Triplet Fusion
- the TTF mechanism utilizes the phenomenon that singlet excitons are generated by the collision of two triplet excitons, and it is theoretically thought that the internal quantum efficiency can be increased to 40%.
- Patent Document 2 discloses an organic EL device using a TADF (Thermally Activated Delayed Fluorescence) mechanism.
- the TADF mechanism utilizes the phenomenon that an intersystem crossing from a triplet exciter to a singlet exciter occurs in a material in which the energy difference between the singlet level and the triplet level is small, and theoretically determines the internal quantum efficiency. It is believed that it can be increased to 100%. However, as with the phosphorescent light emitting device, further improvement in life characteristics is required.
- Patent Document 3 discloses the use of an indolocarbazole compound as a host material.
- Patent Document 4 discloses the use of a biscarbazole compound as a host material.
- Patent Documents 5 and 6 disclose that a biscarbazole compound is used as a mixed host.
- Patent Documents 7, 8, 9, and 10 disclose that an indolocarbazole compound and a biscarbazole compound are used as a mixed host.
- Patent Document 11 discloses the use of a host material in which a plurality of hosts containing an indolocarbazole compound are premixed. However, none of them can be said to be sufficient, and further improvement is desired.
- An object of the present invention is to provide an organic EL device having high efficiency and high drive stability while having a low drive voltage.
- At least one light emitting layer is a first host selected from a compound represented by the following general formula (1). It is an organic EL device characterized by comprising a second host selected from a compound represented by the following general formula (2), and a vapor-deposited layer containing a luminescent dopant material.
- ring A is an aromatic hydrocarbon ring represented by the formula (1a)
- ring B is a heterocycle represented by the formula (1b)
- ring A and ring B are adjacent rings and arbitrary.
- Condensed at the position of Ar 1 is a phenyl group, a biphenyl group or a terphenyl group
- R is independently an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aromatic heterocyclic group having 3 to 12 carbon atoms.
- a, b, and c each independently represent an integer of 0 to 3
- m and n indicate the number of repetitions, and each independently represents an integer of 0 to 4.
- m n does not hold, and m + n ⁇ 2.
- Ar 2 and Ar 3 represent an aromatic hydrocarbon group having 6 to 14 carbon atoms, or a group in which 2 to 3 aromatic hydrocarbon groups are linked, and at least one of Ar 2 and Ar 3 is a condensed aromatic group. Represents a group hydrocarbon group.
- a preferred embodiment of the general formula (2) is the general formula (3).
- Preferred embodiments of the general formula (1) include general formulas (4) to (9), preferably general formulas (4), (5), (6), or (7), and more preferably. It is the general formula (4).
- the first host and the second host are premixed and used before vapor deposition.
- the difference in 50% weight loss temperature between the first host and the second host is within 20 ° C, or the ratio of the first host is more than 20 wt% with respect to the total of the first host and the second host. More, preferably less than 55wt%.
- the luminescent dopant material can be a phosphorescent dopant material, a fluorescence luminescent dopant material, or a heat-activated delayed fluorescence dopant material.
- Phosphorescent dopant materials include organic metal complexes containing at least one metal selected from ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum and gold.
- the organic EL device is provided with a hole blocking layer adjacent to the light emitting layer, and the hole blocking layer contains the compound represented by the general formula (1).
- the present invention includes a step of mixing the first host and the second host to form a premixture, and then depositing a host material containing the host material to form a light emitting layer. This is a method for manufacturing an organic electroluminescent device.
- the material used for the organic layer has high durability against electric charges, and it is particularly important to suppress leakage of excitons and electric charges to the peripheral layer in the light emitting layer.
- it is effective to improve the bias of the light emitting region in the light emitting layer, and for that purpose, the amount of both charges (electrons / holes) injected into the light emitting layer or the transport of both charges in the light emitting layer. It is necessary to control the amount within a preferable range.
- the indolocarbazole compound of the general formula (1) has high skeletal stability, and both charge injection transportability can be controlled to some extent by isomers and substituents, but when used alone, both charges are as described above. It is difficult to control the injection transport volume within a preferable range.
- the biscarbazole compound of the general formula (2) can be controlled at a high level of charge injection transportability by changing the type and number of substituents.
- this biscarbazole compound has high amorphous stability and, like the indolocarbazole compound, has high skeletal stability.
- the amount of charge injected into the organic layer can be adjusted within a preferable range, and better device characteristics can be expected.
- a delayed fluorescence EL element or a phosphorescent EL element since it has a minimum excitation triplet energy sufficiently high to confine the excitation energy generated in the light emitting layer, it is generated from within the light emitting layer. There is no energy outflow, and high efficiency and long life can be achieved at low voltage.
- the organic EL device of the present invention has one or more light emitting layers between the opposing anode and cathode, and at least one of the light emitting layers contains a first host and a second host, and a light emitting dopant material. Consists of a vapor deposition layer. This vapor deposition layer can be produced by vacuum deposition.
- the first host is a compound represented by the general formula (1)
- the second host is a compound represented by the general formula (2).
- This organic EL device has an organic layer composed of a plurality of layers between the opposite anode and the cathode, and at least one of the plurality of layers is a light emitting layer, and a plurality of light emitting layers may be provided.
- Ring A is an aromatic hydrocarbon ring represented by the formula (1a)
- ring B is a heterocycle represented by the formula (1b)
- rings A and B are adjacent rings and at arbitrary positions. Condensate.
- Ar 1 represents a phenyl group, a biphenyl group, or a terphenyl group. It is preferably a phenyl group or a biphenyl group, and more preferably a phenyl group.
- the biphenyl group is a group represented by -Ph-Ph
- the terphenyl group is a group represented by -Ph-Ph-Ph or Ph (-Ph) -Ph.
- Ph is a phenyl group, a phenylene group, or the like.
- R independently represents an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or an aromatic heterocyclic group having 3 to 12 carbon atoms.
- it represents an aliphatic hydrocarbon group having 1 to 8 carbon atoms, a phenyl group, or an aromatic heterocyclic group having 3 to 9 carbon atoms. More preferably, it is an aliphatic hydrocarbon group having 1 to 6 carbon atoms, a phenyl group, or an aromatic heterocyclic group having 3 to 6 carbon atoms.
- aliphatic hydrocarbon group having 1 to 10 carbon atoms include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl and the like. It is preferably an alkyl group having 1 to 4 carbon atoms.
- aromatic hydrocarbon group having 6 to 10 carbon atoms or the aromatic heterocyclic group having 3 to 12 carbon atoms include benzene, naphthalene, pyridine, pyrimidine, triazine, thiophene, isothiazole, thiazole, pyridazine, and the like.
- A, b, and c represent the number of substitutions, and each independently represents an integer of 0 to 3, and is preferably an integer of 0 or 1.
- m + n is preferably an integer of 2 or more, and more preferably an integer of 2 or 3.
- Ar 2 and Ar 3 represent an aromatic hydrocarbon group having 6 to 14 carbon atoms or a linked aromatic group in which 2 to 3 aromatic hydrocarbon groups are linked. It preferably represents an aromatic hydrocarbon group having 6 to 12 carbon atoms, more preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms, but at least one of Ar 2 and Ar 3 is a condensed aromatic hydrocarbon group. ..
- Ar 2 and Ar 3 are generated by taking one H from an aromatic hydrocarbon such as benzene, naphthalene, anthracene, phenanthrene, or fluorene, or a compound in which two aromatic rings of these aromatic hydrocarbons are linked.
- Aromatic groups or linked aromatic groups can be mentioned. Preferred are aromatic groups derived from benzene, naphthalene, anthracene and phenanthrene, or linked aromatic groups in which two aromatic groups thereof are linked, and more preferably aromatic groups derived from benzene, naphthalene or phenanthrene. .. It is more preferable that Ar 3 is a naphthyl group or a phenanthryl group.
- the aromatic group or the linking aromatic group may have a substituent, and the preferred substituent is an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms.
- the linked aromatic group is represented by an equation such as -Ar 4 -Ar 5 .
- Ar 4 and Ar 5 are independently aromatic hydrocarbon groups having 6 to 14 carbon atoms.
- Ar 4 is a divalent or trivalent group and Ar 5 is monovalent.
- the aromatic groups constituting the linked aromatic groups may be the same or different.
- An excellent organic EL by using the first host selected from the compound represented by the general formula (1) and the second host selected from the compound represented by the general formula (2) as the host material of the light emitting layer.
- the element can be provided.
- the first host and the second host can be used by vapor deposition from different vapor deposition sources individually, but they are premixed before vapor deposition to form a premixture, and the premixture is simultaneously vapor-deposited from one vapor deposition source to emit light. It is preferable to form a layer.
- the premix may be mixed with the luminescent dopant material required to form the light emitting layer or other hosts used as needed, but there is a large difference in the temperature at which the desired vapor pressure is achieved. In that case, it is preferable to vapor-deposit from another vapor deposition source.
- the ratio of the first host to the total of the first host and the second host is preferably 20 to 60%, preferably more than 20%. , 55%, more preferably 40-50%.
- FIG. 1 is a cross-sectional view showing a structural example of a general organic EL device used in the present invention, in which 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 represent 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, or may have an electron blocking layer between the light emitting layer and the hole injection layer.
- the exciton blocking layer can be inserted into either the cathode side or the cathode side of the light emitting layer, and both can be inserted at the same time.
- the organic EL device of the present invention has an anode, a light emitting layer, and a cathode as essential layers, but it is preferable to have a hole injection transport layer and an electron injection transport layer in addition to the essential layers, and further, a light emitting layer and electron injection. It is preferable to have a hole blocking layer between the transport layers.
- the hole injection transport layer means either or both of the hole injection layer and the hole transport layer
- the electron injection transport layer means either or both of the electron injection layer and the electron transport layer.
- the structure opposite to that of FIG. 1, that is, the cathode 7, the electron transport layer 6, the light emitting layer 5, the hole transport layer 4, and the anode 2 can be laminated in this order on the substrate 1, and in this case as well, the layers can be laminated in this order. It can be added or omitted.
- the organic EL device of the present invention is preferably supported by a substrate.
- the substrate is not particularly limited as long as it is conventionally used for an organic EL element, and for example, a substrate made of glass, transparent plastic, quartz or the like can be used.
- anode material in the organic EL element a material having a large work function (4 eV or more), an alloy, an electrically conductive compound, or a mixture thereof 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 producing a transparent conductive film may be used.
- a thin film may be formed by forming a thin film of these electrode materials by a method such as thin film deposition or sputtering, and a pattern having a desired shape may be formed by a photolithography method, or when pattern accuracy is not required so much (about 100 ⁇ m or more). May form a pattern through a mask having a desired shape during vapor deposition or sputtering of the electrode material.
- a coatable substance such as an organic conductive compound
- a wet film forming method such as a printing method or a coating method can also be used.
- the sheet resistance as the anode is preferably several hundred ⁇ / ⁇ or less.
- the film thickness depends on the material, but is usually selected in the range of 10 to 1000 nm, preferably 10 to 200 nm.
- the cathode material a material having a small work function (4 eV or less) (electron-injectable metal), an alloy, an electrically conductive compound, or a mixture thereof 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 ) Examples thereof include a mixture, an indium, a lithium / aluminum mixture, and a rare earth metal.
- a mixture of an electron injectable metal and a second metal which is a stable metal having a larger work function value than this for example, magnesium / silver mixture, magnesium / Aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide mixture, lithium / aluminum mixture, aluminum and the like are suitable.
- the cathode can be produced by forming a thin film of these cathode materials by a method such as vapor deposition or sputtering.
- the sheet resistance of 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 emission brightness is improved, which is convenient.
- a transparent or translucent cathode can be produced by forming the above metal on the cathode with a thickness of 1 to 20 nm and then forming the conductive transparent material mentioned in the description of the anode on the cathode. By applying this, it is possible to manufacture an element in which both the anode and the cathode are transparent.
- 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 contains an organic light emitting dopant material and a host material.
- the first host represented by the general formula (1) and the second host represented by the general formula (2) are used. Further, one or a plurality of known host materials may be used in combination, but the amount used may be 50 wt% or less, preferably 25 wt% or less, based on the total amount of the host materials.
- the first host and the second host can be vapor-deposited from different vapor deposition sources, or the first host and the second host can be vapor-deposited from one vapor deposition source at the same time by premixing them before vapor deposition to form a premix. ..
- the 50% weight loss temperature is the temperature at which the weight is reduced by 50% when the temperature is raised from room temperature to 550 ° C at a rate of 10 ° C per minute in TG-DTA measurement under nitrogen airflow reduced pressure (50 Pa). .. It is considered that vaporization by evaporation or sublimation occurs most actively in the vicinity of this temperature.
- the difference between the 50% weight loss temperature of the first host and the second host is preferably within 20 ° C, more preferably within 15 ° C.
- a known method such as pulverization and mixing can be adopted, but it is desirable to mix as uniformly as possible.
- the phosphorescent dopant When a phosphorescent dopant is used as the luminescent dopant material, the phosphorescent dopant contains an organic metal complex containing at least one metal selected from ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum and gold. What to do is good. Specifically, the iridium complexes described in J.Am.Chem.Soc.2001,123,4304 and JP-A-2013-53051 are preferably used, but are not limited thereto.
- the phosphorescent dopant material only one type may be contained in the light emitting layer, or two or more types may be contained.
- the content of the phosphorescent dopant material is preferably 0.1 to 30 wt% and more preferably 1 to 20 wt% with respect to the host material.
- the phosphorescent dopant material is not particularly limited, but specific examples include the following.
- the fluorescent light emitting dopant is not particularly limited, and is, for example, a benzoxazole derivative, a benzothiazole derivative, a benzoimidazole derivative, a styrylbenzene derivative, a polyphenyl derivative, a diphenylbutadiene derivative, or a tetraphenyl.
- polymer compounds such as polyphenylene and polyphenylene vinylene, and organic silane derivatives.
- Preferred are condensed aromatic derivatives, styryl derivatives, diketopyrrolopyrrole derivatives, oxazine derivatives, pyromethene metal complexes, transition metal complexes, or lanthanoid complexes, and more preferably naphthalene, pyrene, chrysene, triphenylene, benzo [c] phenanthrene.
- Benzo [a] anthracene pentacene, perylene, fluorantene, acenafusofluoranthen, dibenzo [a, j] anthracene, dibenzo [a, h] anthracene, benzo [a] naphthalene, hexacene, naphtho [2,1-f] ] Isoquinoline, ⁇ -naphthaphenanthridin, phenanthrooxazole, quinolino [6,5-f] quinoline, benzothiophantrene and the like. These may have an alkyl group, an aryl group, an aromatic heterocyclic group, or a diarylamino group as a substituent.
- the fluorescent light emitting dopant material only one kind may be contained in the light emitting layer, or two or more kinds may be contained.
- the content of the fluorescent dopant material is preferably 0.1 to 20%, more preferably 1 to 10% with respect to the host material.
- the heat-activated delayed fluorescence light-emitting dopant is not particularly limited, but is described in a metal complex such as a tin complex or a copper complex, or as described in WO2011 / 070963.
- the heat-activated delayed fluorescence-emitting dopant material is not particularly limited, but specific examples include the following.
- the heat activation delayed fluorescence light emitting dopant material only one kind may be contained in the light emitting layer, or two or more kinds may be contained. Further, the heat-activated delayed fluorescence emission dopant may be mixed with a phosphorescence emission dopant or a fluorescence emission dopant.
- the content of the heat-activated delayed fluorescence dopant material is preferably 0.1 to 50%, more preferably 1 to 30% with respect to the host material.
- the injection layer is a layer provided between the electrode and the organic layer in order to reduce the driving voltage and improve the emission brightness.
- the injection layer can be provided as needed.
- the hole blocking layer has the function of an electron transporting layer in a broad sense, and is made of a hole blocking material having a function of transporting electrons and a significantly small ability to transport holes, and a hole while transporting electrons. It is possible to improve the recombination probability of electrons and holes in the light emitting layer by blocking the above.
- a known hole blocking layer material can be used for the hole blocking layer, but it is preferable to contain a compound represented by the general formula (1).
- the electron blocking layer has a function of a hole transporting layer in a broad sense, and by blocking electrons while transporting holes, the probability of recombination of electrons and holes in the light emitting layer can be improved. ..
- the material of the electron blocking layer a known electron blocking layer material can be used, and a hole transporting layer material described later can be used as needed.
- the film 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 for blocking excitons generated by the recombination of holes and electrons in the light emitting layer from diffusing into the charge transport layer, and the excitons are inserted by inserting this layer. It is possible to efficiently confine it in the light emitting layer, and it is possible to improve the light emitting efficiency of the element.
- the exciton blocking layer can be inserted between two adjacent light emitting layers in an element in which two or more light emitting layers are adjacent to each other.
- exciton blocking layer As the material of the exciton blocking layer, a known exciton blocking layer material can be used. For example, 1,3-dicarbazolylbenzene (mCP) and bis (2-methyl-8-quinolinolato) -4-phenylphenylatoaluminum (III) (BAlq) can be mentioned.
- mCP 1,3-dicarbazolylbenzene
- BAlq bis (2-methyl-8-quinolinolato) -4-phenylphenylatoaluminum
- the hole transport layer is made of a hole transport material having a function of transporting holes, and the hole transport layer may be provided as a single layer or a plurality of layers.
- the hole transport material has any of hole injection or transport and electron barrier property, and may be either an organic substance or an inorganic substance. Any compound can be selected and used for the hole transport layer from conventionally known compounds. Examples of such hole transporting materials include porphyrin derivatives, arylamine derivatives, triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, and amino-substituted chalcone derivatives.
- the electron transport layer is made of a material having a function of transporting electrons, and the electron transport layer may be provided with a single layer or a plurality of layers.
- the electron transport material (which may also serve as a hole blocking material) may have a function of transmitting electrons injected from the cathode to the light emitting layer.
- any of conventionally known compounds can be selected and used.
- polycyclic aromatic derivatives such as naphthalene, anthracene and phenanthroline, tris (8-quinolinolate) aluminum (III).
- Derivatives phosphine oxide derivatives, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carbodiimide, freolenidene methane derivatives, anthracinodimethane and antron derivatives, bipyridine derivatives, quinoline derivatives, oxadiazole derivatives, benzoimidazole Derivatives, benzothiazole derivatives, indolocarbazole derivatives and the like can be mentioned. Further, 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.
- Example 1 Each thin film was laminated with a vacuum degree of 4.0 ⁇ 10 -5 Pa by a vacuum vapor deposition method on a glass substrate on which an anode made of ITO having a film thickness of 110 nm was formed.
- HAT-CN was formed on the ITO to a thickness of 25 nm as a hole injection layer, and then NPD was formed to a thickness of 30 nm as a hole transport layer.
- HT-1 was formed to a thickness of 10 nm as an electron blocking layer.
- compound 1-1 as the first host, compound 2-1 as the second host, and Ir (ppy) 3 as the light emitting dopant are co-deposited from different vapor deposition sources to form a light emitting layer having a thickness of 40 nm. did.
- co-deposited under the vapor deposition conditions where the concentration of Ir (ppy) 3 was 10 wt% and the weight ratio between the first host and the second host was 30:70.
- ET-1 was formed to a thickness of 20 nm as an electron transport layer.
- LiF was formed on the electron transport layer as an electron injection layer to a thickness of 1 nm.
- Al was formed as a cathode on the electron injection layer to a thickness of 70 nm to prepare an organic EL device.
- Example 2-14 an organic EL device was produced in the same manner as in Example 1 except that the compounds shown in Table 1 were used as the first host and the second host.
- Example 15-17 The first and second hosts were premixed to form a premix, which was co-deposited from the same deposition source.
- the organic EL is the same as in Example 1 except that the premix obtained by weighing the first host (0.30 g) and the second host (0.70 g) and mixing them while grinding in a mortar was used. The element was manufactured.
- Examples 18-23 The first host and the second host were mixed in advance to prepare a premixture, which was co-deposited from the same vapor deposition source to produce an organic EL device further provided with a hole blocking layer.
- compound 1-4 was formed to a thickness of 10 nm as a hole blocking layer
- ET-1 was formed to a thickness of 10 nm as an electron transport layer after the light emitting layer was formed.
- Organic EL devices were produced in the same manner as in Examples 15 to 17.
- Table 1 shows the evaluation results of the produced organic EL device.
- the brightness, drive voltage, and luminous efficiency are the values when the drive current is 20 mA / cm 2 and are the initial characteristics.
- LT70 is the time required for the initial brightness to decay to 70%, and represents the life characteristic.
- Example 1 an organic EL device was produced in the same manner as in Example 1 except that Compound 1-1 was used alone as a host.
- the thickness of the light emitting layer and the concentration of the light emitting dopant are the same as in Example 1.
- Comparative Examples 2 to 8 An organic EL device was produced in the same manner as in Comparative Example 1 except that the compounds shown in Table 2 were used alone as the host.
- Example 1 an organic EL device was produced in the same manner as in Example 1 except that compound A was used as the first host and compound 2-1 or compound 2-3 was used as the second host.
- Comparative Examples 11-12 organic EL devices were produced in the same manner as in Comparative Examples 9 to 10 except that Compound B was used as the first host.
- Comparative Examples 13-14 In Comparative Examples 9 to 10, organic EL devices were produced in the same manner as in Comparative Examples 9 to 10 except that Compound C was used as the first host.
- Comparative Examples 15 to 16 organic EL devices were produced in the same manner as in Comparative Examples 9 to 10 except that Compound D was used as the first host.
- Table 2 shows the evaluation results of the manufactured organic EL device.
- Examples 1 to 23 have improved power efficiency and life characteristics, and exhibit good characteristics.
- Example 24 Each thin film was laminated with a vacuum degree of 4.0 ⁇ 10 -5 Pa by a vacuum vapor deposition method on a glass substrate on which an anode made of ITO having a film thickness of 110 nm was formed.
- HAT-CN was formed on the ITO to a thickness of 25 nm as a hole injection layer, and then NPD was formed to a thickness of 45 nm as a hole transport layer.
- HT-1 was formed to a thickness of 10 nm as an electron blocking layer.
- compound 1-1 was co-deposited as the first host, compound 2-1 was co-deposited as the second host, and Ir (piq) 2 acac as the light emitting dopant from different vapor deposition sources, and the light emitting layer was formed to a thickness of 40 nm. Formed. At this time, co-deposited under the vapor deposition conditions where the concentration of Ir (piq) 2 acac was 6.0 wt%. Next, ET-1 was formed to a thickness of 37.5 nm as an electron transport layer. Then, LiF was formed on the electron transport layer as an electron injection layer to a thickness of 1 nm. Finally, Al was formed as a cathode on the electron injection layer to a thickness of 70 nm to prepare an organic EL device.
- Example 25-37 an organic EL device was produced in the same manner as in Example 24 except that the compounds shown in Table 3 were used as the first host and the second host.
- Table 3 shows the evaluation results of the manufactured organic EL device.
- LT95 is the time required for the initial brightness to be attenuated to 95%, and represents the life characteristic.
- Example 24 an organic EL device was produced in the same manner as in Example 24 except that Compound 1-1 was used alone as a host.
- the thickness of the light emitting layer and the concentration of the light emitting dopant are the same as in Example 24.
- Comparative Examples 18 to 24 An organic EL device was produced in the same manner as in Comparative Example 17 except that the compounds shown in Table 4 were used alone as the host.
- Example 24 an organic EL device was produced in the same manner as in Example 24 except that compound A was used as the first host and compound 2-1 or compound 2-3 was used as the second host.
- Comparative Examples 27-28 organic EL devices were produced in the same manner as in Comparative Examples 25 to 26 except that Compound B was used as the first host.
- Comparative Examples 29 to 30 organic EL devices were produced in the same manner as in Comparative Examples 25 to 26 except that Compound C was used as the first host.
- Comparative Examples 31 to 32 organic EL devices were produced in the same manner as in Comparative Examples 25 to 26 except that Compound D was used as the first host.
- Table 4 shows the evaluation results of the manufactured organic EL device.
- Examples 24 to 37 have improved power efficiency and life characteristics, and exhibit good characteristics.
- the organic electroluminescent element of the present invention has less energy outflow from the light emitting layer, and can achieve high efficiency and long life at a low voltage.
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Abstract
Description
しかしながら、燐光発光型の有機EL素子に関しては、長寿命化が技術的な課題となっている。
一方で特許文献2では、TADF(Thermally Activated Delayed Fluorescence)機構を利用した有機EL素子が開示されている。TADF機構は一重項準位と三重項準位のエネルギー差が小さい材料において三重項励起子から一重項励起子への逆項間交差が生じる現象を利用するものであり、理論上内部量子効率を100%まで高められると考えられている。しかしながら、燐光発光型素子と同様に寿命特性の更なる改善が求められている。
しかしながら、いずれも十分なものとは言えず、更なる改良が望まれている。
Ar1はフェニル基、ビフェニル基又はターフェニル基であり、
Rは独立に炭素数1~10の脂肪族炭化水素基、炭素数6~10の芳香族炭化水素基又は炭素数3~12の芳香族複素環基であり、
a、b、cは、各々独立して0~3の整数を表し、
mとnは、繰返し数を示し、各々独立して0~4の整数を表す。但し、m=nとなることはなく、m+n≧2である。
ここで、一般式(1)のインドロカルバゾール化合物は、骨格の安定性が高く、異性体や置換基によって両電荷注入輸送性をある程度制御することができるが単独では、上述のように両電荷注入輸送量を好ましい範囲に制御するのは難しい。一方で、一般式(2)のビスカルバゾール化合物は、置換基の種類・数を変えることで電荷注入輸送性が高いレベルで制御できる。加えて、このビスカルバゾール化合物は、アモルファス安定性が高く、インドロカルバゾール化合物と同様に骨格安定性が高い。そこで、上記インドロカルバゾール化合物とビスカルバゾール化合物を混合して用いることで、有機層への電荷注入量を好ましい範囲に調整でき、より良好な素子特性が期待できる。特に、遅延蛍光発光EL素子や燐光発光EL素子の場合にあっては、発光層で生成する励起エネルギーを閉じ込めるのに十分高い最低励起三重項エネルギーを有していることから、発光層内からのエネルギー流出がなく、低電圧で高効率かつ長寿命を達成できる。
環Aは式(1a)で表される芳香族炭化水素環であり、環Bは式(1b)で表される複素環であり、環A及び環Bはそれぞれ隣接する環と任意の位置で縮合する。
Ar2とAr3は炭素数6~14の芳香族炭化水素基、又は該芳香族炭化水素基が2~3個連結した連結芳香族基を表す。好ましくは、炭素数6~12の芳香族炭化水素基、より好ましくは炭素数6~10の芳香族炭化水素基を表すが、Ar2とAr3の少なくとも一方は縮合芳香族炭化水素基である。
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素子に用いられているものであれば良く、例えばガラス、透明プラスチック、石英等からなるものを用いることができる。
有機EL素子における陽極材料としては、仕事関数の大きい(4eV以上)金属、合金、電気伝導性化合物又はこれらの混合物からなる材料が好ましく用いられる。このような電極材料の具体例としては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)等の非晶質で、透明導電膜を作成可能な材料を用いてもよい。陽極はこれらの電極材料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良く、あるいはパターン精度をあまり必要としない場合(100μm以上程度)は、上記電極材料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な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。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、陰極材料としては仕事関数の小さい(4eV以下)金属(電子注入性金属)、合金、電気伝導性化合物又はこれらの混合物からなる材料が用いられる。このような電極材料の具体例としては、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。陰極はこれらの陰極材料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は向上し、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性ドーパント材料とホスト材料を含む。
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発光層中での電子と正孔の再結合確率を向上させることができる。
電子阻止層とは広い意味では正孔輸送層の機能を有し、正孔を輸送しつつ電子を阻止することで発光層中での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、本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2つ以上の発光層が隣接する素子において、隣接する2つの発光層の間に挿入することができる。
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110nmの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4.0×10-5Paで積層した。まず、ITO上に正孔注入層としてHAT-CNを25nmの厚さに形成し、次に正孔輸送層としてNPDを30nmの厚さに形成した。次に電子阻止層としてHT-1を10nmの厚さに形成した。次に、第1ホストとして化合物1-1を、第2ホストとして化合物2-1を、発光ドーパントとしてIr(ppy)3をそれぞれ異なる蒸着源から共蒸着し、40nmの厚さに発光層を形成した。この時、Ir(ppy)3の濃度が10wt%、第1ホストと第2ホストの重量比が30:70となる蒸着条件で共蒸着した。次に電子輸送層としてET-1を20nm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LiFを1nmの厚さに形成した。最後に、電子注入層上に、陰極としてAlを70nmの厚さに形成し、有機EL素子を作製した。
実施例1において、第1ホスト及び第2ホストを、表1に示す化合物を使用した以外は実施例1と同様にして有機EL素子を作製した。
第1ホストと第2ホストを事前に混合し、予備混合物とし、これを同じ蒸着源から共蒸着した。
実施例1において、第一ホスト(0.30g)と第二ホスト(0.70g)を量りとり、乳鉢ですり潰しながら混合することにより得た予備混合物を使用した以外は実施例1と同様にして有機EL素子を作製した。
第1ホストと第2ホストを事前に混合し、予備混合物とし、これを同じ蒸着源から共蒸着し、更に正孔阻止層を設けた有機EL素子を作製した。
実施例15~17において、発光層を形成した後、正孔阻止層として化合物1-4を10nmの厚さに形成し、電子輸送層としてET-1を10nmの厚さに形成した以外は実施例15~17と同様にして有機EL素子を作製した。
実施例1において、ホストとして化合物1-1を単独で用いた以外は実施例1と同様にして有機EL素子を作製した。発光層の厚み、発光ドーパント濃度は実施例1と同様である。
ホストとして表2に示す化合物を単独で用いた以外は比較例1と同様にして有機EL素子を作製した。
実施例1において、第1ホストとして化合物Aを、第2ホストとして化合物2-1又は化合物2-3を使用した以外は実施例1と同様にして有機EL素子を作製した。
比較例9~10において、第1ホストとして化合物Bを使用した以外は比較例9~10と同様にして有機EL素子を作製した。
比較例9~10において、第1ホストとして化合物Cを使用した以外は比較例9~10と同様にして有機EL素子を作製した。
比較例9~10において、第1ホストとして化合物Dを使用した以外は比較例9~10と同様にして有機EL素子を作製した。
膜厚110nmの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4.0×10-5Paで積層した。まず、ITO上に正孔注入層としてHAT-CNを25nmの厚さに形成し、次に正孔輸送層としてNPDを45nmの厚さに形成した。次に、電子阻止層としてHT-1を10nmの厚さに形成した。次に、第1ホストとして化合物1-1を、第2ホストとして化合物2-1を、発光ドーパントとしてIr(piq)2acacをそれぞれ異なる蒸着源から共蒸着し、40nmの厚さに発光層を形成した。この時Ir(piq)2acacの濃度が6.0wt%となる蒸着条件で共蒸着した。次に電子輸送層としてET-1を37.5nmの厚さに形成した。そして電子輸送層上に電子注入層としてLiFを1nmの厚さに形成した。最後に、電子注入層上に、陰極としてAlを70nmの厚さに形成し、有機EL素子を作製した。
実施例24において、第1ホスト及び第2ホストを、表3に示す化合物を使用した以外は実施例24と同様にして有機EL素子を作製した。
実施例24において、ホストとして化合物1-1を単独で用いた以外は実施例24と同様にして有機EL素子を作製した。発光層の厚み、発光ドーパント濃度は実施例24と同様である。
ホストとして表4に示す化合物を単独で用いた以外は比較例17と同様にして有機EL素子を作製した。
実施例24において、第1ホストとして化合物Aを、第2ホストとして化合物2-1又は化合物2-3を使用した以外は実施例24と同様にして有機EL素子を作製した。
比較例25~26において、第1ホストとして化合物Bを使用した以外は比較例25~26と同様にして有機EL素子を作製した。
比較例25~26において、第1ホストとして化合物Cを使用した以外は比較例25~26と同様にして有機EL素子を作製した。
比較例25~26において、第1ホストとして化合物Dを使用した以外は比較例25~26と同様にして有機EL素子を作製した。
Claims (10)
- 対向する陽極と陰極の間に、1つ以上の発光層を含む有機電界発光素子において、少なくとも1つの発光層が、下記一般式(1)で表される化合物から選ばれる第1ホストと下記一般式(2)で表される化合物から選ばれる第2ホスト、及び発光性ドーパント材料を含有する蒸着層からなることを特徴とする有機電界発光素子。
Ar1はフェニル基、ビフェニル基又はターフェニル基であり、
Rは独立に炭素数1~10の脂肪族炭化水素基、炭素数6~10の芳香族炭化水素基又は炭素数3~12の芳香族複素環基であり、
a、b、cは、各々独立して0~3の整数を表し、
mとnは、繰返し数を示し、各々独立して0~4の整数を表す。但し、m=nとなることはなく、m+n≧2である。
- Ar2がナフチル基又はフェナンスリル基であることを特徴とする請求項1に記載の有機電界発光素子。
- 第1ホストと第2ホストの合計に対し、第1ホストの割合が20wt%を超え、55 wt%未満であることを特徴とする請求項1に記載の有機電界発光素子。
- 発光性ドーパント材料が、ルテニウム、ロジウム、パラジウム、銀、レニウム、オスミウム、イリジウム、白金及び金からなる群れから選ばれる少なくとも一つの金属を含む有機金属錯体であることを特徴とする請求項1に記載の有機電界発光素子。
- 発光性ドーパント材料が、熱活性化遅延蛍光発光ドーパント材料であることを特徴とする請求項1に記載の有機電界発光素子。
- 発光層と隣接して正孔阻止層を設け、該正孔阻止層中に一般式(1)で表される化合物を含有させることを特徴とする請求項1に記載の有機電界発光素子。
- 請求項1~8のいずれかに記載の有機電界発光素子を製造するに当たり、第1ホストと第2ホストを混合して予備混合物としたのち、これを含むホスト材料を蒸着させて発光層を形成させる工程を有することを特徴とする有機電界発光素子の製造方法。
- 第1ホストと第2ホストの50%重量減少温度の差が20℃以内であることを特徴する請求項9に記載の有機電界発光素子の製造方法。
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Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011070963A1 (ja) | 2009-12-07 | 2011-06-16 | 新日鐵化学株式会社 | 有機発光材料及び有機発光素子 |
JP2013053051A (ja) | 2011-09-06 | 2013-03-21 | Sumitomo Electric Ind Ltd | ダイヤモンド複合体およびそれから分離した単結晶ダイヤモンド、及びダイヤモンド複合体の製造方法 |
US20160260905A1 (en) * | 2015-03-03 | 2016-09-08 | Samsung Display Co., Ltd. | Organic light-emitting device |
WO2016194604A1 (ja) * | 2015-05-29 | 2016-12-08 | 新日鉄住金化学株式会社 | 有機電界発光素子 |
US20170117486A1 (en) * | 2015-10-27 | 2017-04-27 | Samsung Display Co., Ltd. | Organic light-emitting device |
WO2018061446A1 (ja) * | 2016-09-30 | 2018-04-05 | 新日鉄住金化学株式会社 | 有機電界発光素子 |
WO2018123783A1 (ja) * | 2016-12-27 | 2018-07-05 | 新日鉄住金化学株式会社 | 有機電界発光素子用材料及び有機電界発光素子 |
WO2018198844A1 (ja) * | 2017-04-27 | 2018-11-01 | 新日鉄住金化学株式会社 | 有機電界発光素子 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003133075A (ja) | 2001-07-25 | 2003-05-09 | Toray Ind Inc | 発光素子 |
WO2008056746A1 (fr) | 2006-11-09 | 2008-05-15 | Nippon Steel Chemical Co., Ltd. | Composé pour un dispositif électroluminescent organique et dispositif électroluminescent organique |
US20100295444A1 (en) | 2009-05-22 | 2010-11-25 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device |
CN103026521B (zh) | 2010-04-28 | 2016-11-09 | 通用显示公司 | 沉积预混合的材料 |
WO2013062075A1 (ja) | 2011-10-26 | 2013-05-02 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子および有機エレクトロルミネッセンス素子用材料 |
WO2013112557A1 (en) | 2012-01-26 | 2013-08-01 | Universal Display Corporation | Phosphorescent organic light emitting devices having a hole transporting cohost material in the emissive region |
KR101820865B1 (ko) | 2013-01-17 | 2018-01-22 | 삼성전자주식회사 | 유기광전자소자용 재료, 이를 포함하는 유기발광소자 및 상기 유기발광소자를 포함하는 표시장치 |
EP2821459B1 (en) | 2013-07-01 | 2017-10-04 | Cheil Industries Inc. | Composition and organic optoelectric device and display device |
KR101802861B1 (ko) | 2014-02-14 | 2017-11-30 | 삼성디스플레이 주식회사 | 유기 발광 소자 |
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Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2011070963A1 (ja) | 2009-12-07 | 2011-06-16 | 新日鐵化学株式会社 | 有機発光材料及び有機発光素子 |
JP2013053051A (ja) | 2011-09-06 | 2013-03-21 | Sumitomo Electric Ind Ltd | ダイヤモンド複合体およびそれから分離した単結晶ダイヤモンド、及びダイヤモンド複合体の製造方法 |
US20160260905A1 (en) * | 2015-03-03 | 2016-09-08 | Samsung Display Co., Ltd. | Organic light-emitting device |
WO2016194604A1 (ja) * | 2015-05-29 | 2016-12-08 | 新日鉄住金化学株式会社 | 有機電界発光素子 |
US20170117486A1 (en) * | 2015-10-27 | 2017-04-27 | Samsung Display Co., Ltd. | Organic light-emitting device |
WO2018061446A1 (ja) * | 2016-09-30 | 2018-04-05 | 新日鉄住金化学株式会社 | 有機電界発光素子 |
WO2018123783A1 (ja) * | 2016-12-27 | 2018-07-05 | 新日鉄住金化学株式会社 | 有機電界発光素子用材料及び有機電界発光素子 |
WO2018198844A1 (ja) * | 2017-04-27 | 2018-11-01 | 新日鉄住金化学株式会社 | 有機電界発光素子 |
Non-Patent Citations (4)
Title |
---|
J. AM. CHEM. SOC., vol. 123, 2001, pages 4304 |
NATURE PHOTONICS, vol. 8, 2014, pages 326 |
NATURE, vol. 492, 2012, pages 234 |
See also references of EP3950882A4 |
Also Published As
Publication number | Publication date |
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EP3950882A4 (en) | 2022-12-14 |
EP3950882A1 (en) | 2022-02-09 |
KR20210143850A (ko) | 2021-11-29 |
JPWO2020203202A1 (ja) | 2020-10-08 |
TW202035653A (zh) | 2020-10-01 |
US20220199913A1 (en) | 2022-06-23 |
CN113661226A (zh) | 2021-11-16 |
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