WO2022131123A1 - 有機電界発光素子及びその製造方法 - Google Patents

有機電界発光素子及びその製造方法 Download PDF

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WO2022131123A1
WO2022131123A1 PCT/JP2021/045322 JP2021045322W WO2022131123A1 WO 2022131123 A1 WO2022131123 A1 WO 2022131123A1 JP 2021045322 W JP2021045322 W JP 2021045322W WO 2022131123 A1 WO2022131123 A1 WO 2022131123A1
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substituted
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淳也 小川
紗友里 木寺
雅崇 奥山
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Nippon Steel Chemical and Materials Co Ltd
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Nippon Steel Chemical and Materials Co Ltd
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Priority to EP21906486.2A priority Critical patent/EP4266392A1/en
Priority to CN202180081298.1A priority patent/CN116710534A/zh
Priority to JP2022569925A priority patent/JPWO2022131123A1/ja
Priority to KR1020237022720A priority patent/KR102924924B1/ko
Priority to US18/035,006 priority patent/US20240032322A1/en
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    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
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    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • 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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    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/10—OLED displays
    • H10K59/12—Active-matrix OLED [AMOLED] displays
    • H10K59/121—Active-matrix OLED [AMOLED] displays characterised by the geometry or disposition of pixel elements
    • H10K59/1213—Active-matrix OLED [AMOLED] displays characterised by the geometry or disposition of pixel elements the pixel elements being TFTs
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/90—Multiple hosts in the emissive layer
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/10—OLED displays
    • H10K59/12—Active-matrix OLED [AMOLED] displays
    • H10K59/123—Connection of the pixel electrodes to the thin film transistors [TFT]
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    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/30—Devices specially adapted for multicolour light emission
    • H10K59/38—Devices specially adapted for multicolour light emission comprising colour filters or colour changing media [CCM]

Definitions

  • the present invention relates to an organic electroluminescent device (hereinafter referred to as an organic EL device), and more particularly to an organic EL device containing a specific mixed host material.
  • Patent Document 1 discloses an organic EL device using a TTF (Triplet-Triplet Fusion) mechanism, which is one of the mechanisms of delayed fluorescence.
  • 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%.
  • the efficiency is lower than that of the phosphorescent light emitting type organic EL element, further improvement in efficiency and low voltage characteristics are required.
  • Patent Document 2 discloses an organic EL element using a TADF (Thermally Activated Delayed Fluorescence) mechanism.
  • the TADF mechanism utilizes the phenomenon that reverse intersystem crossing from a triplet exciter to a singlet exciter occurs in a material with a small energy difference between the singlet level and the triplet level, and theoretically determines the internal quantum efficiency. It is believed that it can be increased to 100%.
  • Patent Document 3 discloses that a compound in which a nitrogen-containing 6-membered ring is substituted with indolocarbazole is used as a host material for a light emitting layer.
  • Patent Documents 4 and 5 disclose that a biscarbazole compound is used as a host material.
  • Patent Documents 6 and 7 disclose that a compound in which biscarbazole is replaced with phenylcarbazole is used as a host material.
  • Patent Documents 8, 9, 10 and 11 disclose that a mixed host material containing a biscarbazole compound is used for the light emitting layer.
  • organic EL displays are highly evaluated for their features such as thinness and lightness, high contrast, and high-speed video display, as well as their curved design and flexibility. Widely applied to devices.
  • it is necessary to further reduce the voltage, and as a light source it is inferior to inorganic LEDs in terms of brightness and life, so efficiency and element life are improved. Is required.
  • an organic electroluminescent element using a specific mixed host material for the light emitting layer can solve the above-mentioned problems, and have completed the present invention.
  • an organic electroluminescent device including one or more light emitting layers between an opposing anode and a cathode
  • at least one light emitting layer is selected from the compound represented by the following general formula (1).
  • the present invention relates to an organic electroluminescent device comprising a host, a second host selected from the compounds represented by the following general formula (2) or the general formula (3), and a luminescent dopant material.
  • Ar 1 and Ar 2 are independently substituted or unsubstituted aromatic hydrocarbon groups having 6 to 25 carbon atoms, and substituted or unsubstituted aromatic heterocycles having 3 to 17 carbon atoms, respectively.
  • Ar 1 and Ar 2 are the aromatic heterocyclic group or the linked aromatic group, the group directly bonded to the carbazole ring in the formula is not a carbazolyl group.
  • Each of R 1 is independently a heavy hydrogen, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 18 substituted or unsubstituted carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group having 3 to 17 carbon atoms. It is an aromatic heterocyclic group of. a to d are substitution numbers, a and d are integers of 0 to 4, and b and c are integers of 0 to 3. m and n are repetition numbers, and m and n are independently integers of 0 to 2, and m + n ⁇ 1.
  • Ring A is a heterocycle represented by the formula (1a) that condenses with two adjacent rings.
  • Ar 3 and Ar 4 are independently substituted or unsubstituted aromatic hydrocarbon groups having 6 to 25 carbon atoms, substituted or unsubstituted aromatic heterocyclic groups having 3 to 17 carbon atoms, or aromatics thereof. It is a substituted or unsubstituted linked aromatic group in which 2 to 5 rings are linked.
  • L 1 is a directly bonded, substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms.
  • Each of R 2 is independently deuterium or an aliphatic hydrocarbon group having 1 to 10 carbon atoms.
  • e to j are substitution numbers, e to h are integers of 0 to 4, and i to j are integers of 0 to 2.
  • X is N or CH, and at least one is N.
  • the compound represented by the general formula (1) is preferably represented by the following formula (4) or (5), and more preferably represented by the following formula (5).
  • Ar 1 , Ar 2 , R 1 , a to d, m and n are synonymous with the general formula (1).
  • n is 0 or all of a to d are 0.
  • the general formula (2) is preferably represented by the following formulas (6) to (11), and more preferably represented by the formulas (6) to (8).
  • Ar 3 , Ar 4 , L 1 , R 2 , e, f, i, and X are synonymous with the general formula (2).
  • the general formula (3) is preferably represented by the following formulas (12) to (17), and more preferably represented by the formulas (12) to (14).
  • Ar 3 , Ar 4 , L 1 , R 2 , e to j, and X are synonymous with the general formula (3).
  • X is all N
  • Ar 3 is substituted or unsubstituted
  • the aromatic hydrocarbon group having 6 to 18 carbon atoms, or these aromatic groups are 2 to 5
  • Preferred embodiments include individually linked substituted or unsubstituted linked aromatic groups.
  • the second host is preferably a compound selected from the group consisting of the general formula (2).
  • the light emitting dopant material is an organic metal complex containing at least one metal selected from ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum and gold, or a heat-activated delayed fluorescent light emitting dopant material.
  • ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum and gold or a heat-activated delayed fluorescent light emitting dopant material.
  • the first host and the second host are mixed to form a premixture, and then a host material containing the premixture is vapor-deposited to form a light-emitting layer.
  • the present invention relates to a method for manufacturing an organic electroluminescent element.
  • the difference in 50% weight loss temperature between the first host and the second host is preferably within 20 ° C.
  • This premix can be used in the method for manufacturing the organic electroluminescent device.
  • the biscarbazole compound substituted with the phenylcarbazole represented by the general formula (1) as the first host and the nitrogen-containing compound represented by the general formula (2) or the general formula (3) as the second host It is considered that a low voltage is exhibited by the high hole injection property of the first host and the high electron injection property of the second host by mixing and using the indolocarbazole compound to which the 6-membered ring is bonded. It is considered that an organic EL device showing a low voltage and a good device life can be obtained by good skeletal stability.
  • the organic EL device of the present invention is an organic electroluminescent device having a plurality of organic layers between an anode and a cathode, the organic layer includes at least one light emitting layer, and the light emitting layer is the general formula (1). ), The second host represented by the general formula (2) or (3), and the dopant material.
  • the two carbazole rings bonded on the 3,3'-biscarbazole skeleton can be bonded at the 1-position, 2-position, 3-position, or 4-position, respectively, but preferably 2. It is a combination at the position or the 3rd position.
  • Preferred compounds are represented by formula (4) or formula (5).
  • the common symbols have the same meaning.
  • Ar 1 and Ar 2 are independently substituted or unsubstituted aromatic hydrocarbon groups having 6 to 25 carbon atoms, substituted or unsubstituted aromatic heterocyclic groups having 3 to 17 carbon atoms, or aromatic groups thereof.
  • Ar 1 and Ar 2 are the aromatic heterocyclic group or the linked aromatic group
  • the group directly bonded to N of the carbazole ring in the formula is not a carbazolyl group. That is, if it is an aromatic heterocyclic group, it is not a carbazolyl group.
  • Ar 1 or Ar 2 is a linked aromatic group such as Ar 11 -Ar 12 -Ar 13- , it is bonded to N.
  • the leading group (Ar 13 ) is not a carbazolyl group.
  • a to d represent the number of substitutions, a and d represent integers of 0 to 4, and b and c represent integers of 0 to 3.
  • a and d are integers of 0 to 2
  • b and c are integers of 0 to 1
  • more preferably all of a to d are 0.
  • M and n represent the number of repetitions, m and n each independently represent an integer of 0 to 2, and m + n ⁇ 1.
  • n is an integer of 0.
  • aromatic hydrocarbon group having 6 to 25 carbon atoms an aromatic heterocyclic group having 3 to 17 carbon atoms, or a linked aromatic group in which 2 to 5 of these aromatic rings are linked.
  • aromatic hydrocarbon group having 6 to 25 carbon atoms an aromatic heterocyclic group having 3 to 17 carbon atoms, or a linked aromatic group in which 2 to 5 of these aromatic rings are linked.
  • examples include benzene, naphthalene, acenaften, acenaphtylene, azulene, anthracene, chrysen, pyrene, phenanthrene, fluorene, triphenylene, pyridine, pyrimidine, triazine, thiophene, isothiazole, thiazole, pyridazine, pyrrol, pyrazole, imidazole, triazole, pyrazine.
  • the resulting group is mentioned.
  • Preferred include benzene, naphthalene, acenaphthene, acenaphthylene, azulene, anthracene, chrysene, pyrene, phenanthrene, fluorene, triphenylene, or groups resulting from compounds composed of 2-5 linkages thereof. More preferably, it is a phenyl group, a biphenyl group, or a terphenyl group.
  • the terphenyl group may be linearly linked or branched. However, the group derived from carbazole is included as a group other than the tip of the linked aromatic group.
  • R 1 is independently a heavy hydrogen or an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an aromatic hydrocarbon group having 6 to 18 substituted or unsubstituted carbon atoms, and 3 to 17 substituted or unsubstituted carbon atoms.
  • aliphatic hydrocarbon group having 1 to 10 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, neopentyl, hexyl, heptyl, octyl, nonyl, decyl and the like. .. Methyl, ethyl, t-butyl, neopentyl are preferred, and methyl is more preferred.
  • R 1 is an unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms and an unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms
  • the unsubstituted aromatic hydrocarbon group has 6 to 18 carbon atoms. It is the same as the case of Ar 1 and Ar 2 above except that it is a group. It is preferably a phenyl group, a pyridine group, a pyrimidine group, a triazine group, a quinazoline group, and more preferably a phenyl group.
  • the linked aromatic group refers to an aromatic group in which carbon atoms of the aromatic ring of two or more aromatic groups are bonded and linked by a single bond.
  • These linked aromatic groups may be linear or branched, but are preferably linear.
  • the connection position when the benzene rings are connected to each other may be ortho, meta, or para, but para-connection or meta-connection is preferable.
  • the aromatic group may be an aromatic hydrocarbon group or an aromatic heterocyclic group, and the plurality of aromatic groups may be the same or different.
  • the aromatic group corresponding to the linked aromatic group is different from the substituted aromatic group.
  • the aromatic hydrocarbon group, the aromatic heterocyclic group, or the linked aromatic group may each have a substituent.
  • the substituents are heavy hydrogen, halogen, cyano group, triarylsilyl group, aliphatic hydrocarbon group having 1 to 10 carbon atoms, alkenyl group having 2 to 5 carbon atoms, and 1 to 5 carbon atoms.
  • An alkoxy group or a diarylamino group having 12 to 44 carbon atoms is preferable, and a heavy hydrogen or an aliphatic hydrocarbon group having 1 to 10 carbon atoms is more preferable.
  • the substituent is an aliphatic hydrocarbon group having 1 to 10 carbon atoms, it may be linear, branched or cyclic.
  • the triarylsilyl group or diarylamino group is replaced with the aromatic ring of the aromatic hydrocarbon group, aromatic heterocyclic group, or linked aromatic group, silicon and carbon, or nitrogen and carbon, respectively. Bonds with a single bond.
  • the number of substituents is preferably 0 to 5, preferably 0 to 2.
  • the carbon number calculation does not include the carbon number of the substituent. However, it is preferable that the total number of carbon atoms including the number of carbon atoms of the substituent satisfies the above range.
  • the above-mentioned substituents are a cyano group, a triarylsilyl group, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, and a diarylamino having 12 to 44 carbon atoms.
  • the groups include cyano, methyl, ethyl, propyl, i-propyl, butyl, t-butyl, pentyl, neopentyl, cyclopentyl, hexyl, cyclohexyl, heptyl, octyl, nonyl, decyl, vinyl, propenyl, butenyl, Examples thereof include pentenyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, diphenylamino, naphthylphenylamino, dinaphthylamino, dianthranylamino, diphenanthrenylamino, dipyrenylamino and the like.
  • Preferred include cyano, methyl, ethyl, t-butyl, propyl, butyl, pentyl, neopentyl, hexyl, heptyl, or octyldiphenylamino, naphthylphenylamino, or dinaphthylamino.
  • the unsubstituted aromatic hydrocarbon group, the unsubstituted aromatic heterocyclic group, the unsubstituted linked aromatic group, or the aliphatic hydrocarbon group is heavy in part or all of hydrogen. It may be hydrocarbonized. When these have substituents, some or all of the hydrogen in the substituents may be deuterated. Further, some or all of the hydrogen in the general formulas (2), (3), and formulas (6) to (17) may be deuterated.
  • the ring A is a heterocyclic ring of the five-membered ring represented by the formula (1a), which is condensed with two adjacent rings at an arbitrary position, but has an edge containing N. Does not condense with. Therefore, the indolocarbazole ring has several isomeric structures, but the number is limited. Specifically, it can have a structure as represented by the above equations (6) to (17). The structure is preferably represented by the formulas (6) to (8) or the formulas (12) to (14), and more preferably the structure represented by the formulas (6) to (8). When it is represented by the general formula (3), it may have an asymmetric structure having isomers of indolocarbazole rings different from each other.
  • X is N or CH independently, and at least one is N. Preferably, two or more of X are N. More preferably, X is all N.
  • E to j represent the number of substitutions, e to h are integers of 0 to 4, and i to j are integers of 0 to 2.
  • e to h are integers of 0 to 2, and more preferably all of e to j are 0.
  • Ar 3 is independently composed of hydrogen, an substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms, or an aromatic ring thereof.
  • it is an unsubstituted linked aromatic group. More preferably, it is a substituted or unsubstituted phenyl group or a substituted or unsubstituted linked aromatic group in which 2 to 3 phenyl groups are linked.
  • aromatic hydrocarbon group having 6 to 25 carbon atoms an aromatic heterocyclic group having 3 to 17 carbon atoms, or a linked aromatic group in which 2 to 5 of these aromatic rings are linked.
  • aromatic hydrocarbon group having 6 to 25 carbon atoms an aromatic heterocyclic group having 3 to 17 carbon atoms, or a linked aromatic group in which 2 to 5 of these aromatic rings are linked.
  • examples include benzene, naphthalene, acenaften, acenaphtylene, azulene, anthracene, chrysen, pyrene, phenanthrene, fluorene, triphenylene, pyridine, pyrimidine, triazine, thiophene, isothiazole, thiazole, pyridazine, pyrrol, pyrazole, imidazole, triazole, pyrazine.
  • the groups that arise from the above are mentioned.
  • Preferred include benzene, naphthalene, acenaphthene, acenaphthylene, azulene, anthracene, chrysene, pyrene, phenanthrene, fluorene, triphenylene, or groups resulting from compounds composed of 2-5 linkages thereof. More preferably, it is a phenyl group, a biphenyl group, or a terphenyl group.
  • the terphenyl group may be linearly linked or branched.
  • Ar 4 is independently composed of hydrogen, an substituted or unsubstituted aromatic hydrocarbon group having 6 to 25 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms, or an aromatic ring thereof. Represents 2-5 linked substituted or unsubstituted linked aromatic groups. Preferably, an substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 12 carbon atoms, or 2 to 5 aromatic hydrocarbon groups are linked. It is a substituted or unsubstituted linked aromatic group.
  • aromatic hydrocarbon group having 6 to 25 carbon atoms an aromatic heterocyclic group having 3 to 17 carbon atoms, or a linked aromatic group in which 2 to 5 of these aromatic rings are linked.
  • aromatic hydrocarbon group having 6 to 25 carbon atoms an aromatic heterocyclic group having 3 to 17 carbon atoms, or a linked aromatic group in which 2 to 5 of these aromatic rings are linked.
  • examples include benzene, naphthalene, acenaften, acenaphtylene, azulene, anthracene, chrysen, pyrene, phenanthrene, fluorene, triphenylene, pyridine, pyrimidine, triazine, thiophene, isothiazole, thiazole, pyridazine, pyrrol, pyrazole, imidazole, triazole, pyrazine.
  • the groups that arise from the above are mentioned.
  • the groups resulting from are mentioned.
  • terphenyl group is a phenyl group, a biphenyl group, a terphenyl group, a pyridine group, a pyrimidine group, a triazine group or a quinazoline group.
  • the terphenyl group may be linearly linked or branched.
  • L 1 represents a directly bonded, substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms. It is preferably a directly bonded, substituted or unsubstituted phenylene group.
  • L 1 is an unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, it is a divalent group produced by removing two hydrogens from an aromatic hydrocarbon compound, and has 6 to 18 carbon atoms. It is the same as the case where Ar 3 is an unsubstituted aromatic hydrocarbon group except that it is an aromatic hydrocarbon group of.
  • R 2 is independently deuterium or an aliphatic hydrocarbon group having 1 to 10 carbon atoms, preferably deuterium, or an aliphatic hydrocarbon group having 1 to 4 carbon atoms, and more preferably deuterium. Is.
  • aliphatic hydrocarbon group having 1 to 10 carbon atoms include methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, neopentyl, hexyl, heptyl, octyl, nonyl, decyl and the like. .. Methyl, ethyl, t-butyl, neopentyl are preferred, and methyl is more preferred.
  • the organic EL device of the present invention has a plurality of organic layers between facing electrodes, and at least one of the organic layers is a light emitting layer. At least one light emitting layer contains the first host and the second host and at least one kind of light emitting dopant.
  • 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 anode 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 an 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 organic EL element 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.
  • 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 of 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 consisting of a metal (electron-injecting metal) having a small work function (4 eV or less), an alloy, an electrically conductive compound, or a mixture thereof is used.
  • a metal electron-injecting metal
  • Specific examples of such 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 include mixtures, indium, lithium / aluminum mixtures, rare earth metals and the like.
  • 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 thin film 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 applying it, 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 each of the anode and cathode, and the light emitting layer contains a light emitting dopant material and a host.
  • the first host and the second host are used.
  • the first host represented by the general formula (1) one kind may be used, or two or more kinds of different compounds may be used.
  • the second host represented by the general formula (2) or (3) may use one kind or two or more different kinds of compounds.
  • one or a plurality of other 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 value of the ionization potential (IP) of the first host represented by the general formula (1) is preferably smaller than 5.9 eV, and the second host represented by the general formula (2) or (3).
  • the absolute value of electron affinity (EA) is preferably larger than 2.5 eV.
  • the EA value can be calculated using the value of the ionization potential (IP) obtained by photoelectron spectroscopy on the host material thin film and the value of the energy gap obtained from the absorption edge by measuring the absorption spectrum. can.
  • a method for manufacturing an organic EL device of the present invention a method of preparing a premixture containing the first host and the second host and using the premixture to prepare a light emitting layer is preferable.
  • a method of vaporizing and depositing the premix from a single evaporation source is more preferred.
  • the premix is a uniform composition.
  • 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 (1 Pa). .. It is considered that vaporization by evaporation or sublimation occurs most actively in the vicinity of this temperature.
  • the difference in 50% weight loss temperature between the first host and the second host in the premixture is preferably within 20 ° C.
  • a uniform vapor deposition film can be obtained.
  • the premix may be mixed with a luminescent dopant material required to form a light emitting layer or, if necessary, another host used, but there is a large difference in the temperature at which the desired vapor pressure is obtained. In that case, it may be vapor-deposited from another vapor deposition source.
  • the ratio of the second host to the total of the first host and the second host is preferably 10 to 70%, preferably more than 15%. , 65%, more preferably 20-60%.
  • a method capable of mixing as uniformly as possible is desirable, and examples thereof include pulverization mixing, heating and melting under reduced pressure or in an atmosphere of an inert gas such as nitrogen, sublimation, and the like. It is not limited to the method.
  • the form of the host and its premixture may be powder, stick or granular.
  • each host can be vapor-deposited from different vapor deposition sources, or multiple types of hosts can be simultaneously vapor-deposited from one vapor deposition source by premixing them before vapor deposition to form a premixture. ..
  • 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, renium, osmium, iridium, platinum and gold. What to do is good.
  • the iridium complex described in J.Am.Chem.Soc.2001,123,4304, JP2013-530515A, US2016 / 0049599A, US2017 / 0069848A, US2018 / 0282356A, US2019 / 0036043A, etc., and US2018 Platinum complexes described in / 0013078A, KR2018-094482A, etc. are preferably used, but are not limited thereto.
  • the phosphorescent 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 phosphorescent dopant material is preferably 0.1 to 30 wt%, 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.
  • Examples thereof include polymer compounds such as polyphenylene and polyphenylene vinylene, and organic silane derivatives.
  • Preferred examples thereof include condensed aromatic derivatives, styryl derivatives, diketopyrrolopyrrole derivatives, oxazine derivatives, pyrromethene metal complexes, transition metal complexes, or lanthanoid complexes, and more preferably naphthalene, pyrene, chrysen, triphenylene, benzo [c] phenanthrene.
  • the heat-activated delayed fluorescence light-emitting dopant is not particularly limited, but is a metal complex such as a tin complex or a copper complex, or an indro described in WO2011 / 070963A.
  • a metal complex such as a tin complex or a copper complex, or an indro described in WO2011 / 070963A.
  • examples thereof include carbazole derivatives, cyanobenzene derivatives described in Nature 2012,492,234, carbazole derivatives, phenazine derivatives, oxadiazole derivatives, triazole derivatives, sulfone derivatives, phenoxazine derivatives, aclysine derivatives and the like described in Nature Photonics 2014,8,326.
  • the thermally activated delayed fluorescent dopant material is not particularly limited, and specific examples thereof include the following.
  • the thermally activated delayed fluorescent dopant material may contain only one type or two or more types in the light emitting layer. Further, the thermally activated delayed fluorescent dopant may be mixed with a phosphorescent light emitting dopant or a fluorescent light emitting dopant. The content of the thermally activated delayed fluorescent 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 includes a hole injection layer and an electron injection layer, and is located between the anode and the light emitting layer or the hole transport layer. And may be present between the cathode and the light emitting layer or the electron transporting layer.
  • 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 is composed of a hole blocking material while transporting electrons. It is possible to improve the recombination probability of electrons and holes in the light emitting layer by blocking the above.
  • 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 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), bis (8-hydroxy-2-methylquinoline)-(4-phenylphenoxy) aluminum (III) (BAlq) and the like can be mentioned.
  • mCP 1,3-dicarbazolylbenzene
  • BAlq bis (8-hydroxy-2-methylquinoline)-(4-phenylphenoxy) aluminum
  • 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 with 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 transport 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 carcon 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 conventionally known compound can be selected and used, for example, a polycyclic aromatic derivative such as naphthalene, anthracene, phenanthroline, tris (8-hydroxyquinoline) aluminum (III).
  • intermediate (A) is 24.8 g (60.7 mmol)
  • intermediate (B) is 25.4 g (78.9 mmol)
  • catalyst A is 0.56 g (0.607 mmol)
  • Sphos is 1.0 g (2.43 mmol)
  • sodium tert. -Butoxide was added in an amount of 14.6 g (151 mmol) and m-xylene was added in an amount of 500 ml, and the mixture was stirred overnight while heating at 160 ° C. After cooling the reaction solution to room temperature, 500 ml of m-xylene and distilled water (1000 ml) were added with stirring. The organic layer was washed with distilled water (3 x 500 ml).
  • intermediate (A) is 24.1 g (58.9 mmol)
  • intermediate (C) is 24.7 g (76.6 mmol)
  • catalyst A is 0.54 g (0.589 mmol)
  • Sphos is 0.97 g (2.36 mmol)
  • sodium tert. -Butoxide was added in an amount of 14.2 g (147 mmol) and m-xylene was added in an amount of 500 ml, and the mixture was stirred overnight while heating at 160 ° C. After cooling the reaction solution to room temperature, 500 ml of m-xylene and distilled water (1000 ml) were added with stirring. The organic layer was washed with distilled water (3 x 500 ml).
  • Example 1 Each thin film was laminated with a vacuum degree of 4.0 ⁇ 10 -5 Pa on a glass substrate having an anode made of ITO with a film thickness of 110 nm formed by a vacuum vapor deposition method.
  • HAT-CN was formed on the ITO to a thickness of 25 nm as a hole injection layer, and then Spiro-TPD 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 2-24 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.
  • 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 on the electron injection layer as a cathode to a thickness of 70 nm to fabricate an organic EL device.
  • Examples 2 to 17, 20 to 23 The compounds shown in Table 1 were used as the first host and the second host, and organic EL devices were produced in the same manner as in Example 1 except that the weight ratios shown in Table 1 were used.
  • Examples 18-19 The compounds shown in Table 1 were used for the first host and the second host, weighed so as to have the weight ratio shown in Table 1, and mixed while grinding in a mortar to obtain a premix.
  • An organic EL device was produced in the same manner as in Example 1 except that this premix was vapor-deposited from one vapor deposition source.
  • Comparative Examples 1 to 10 The compounds shown in Table 2 were used as the first host and the second host, and organic EL devices were produced in the same manner as in Example 1 except that the weight ratios shown in Table 2 were used.
  • Comparative Example 11 An organic EL device was produced in the same manner as in Example 1 except that only the first host shown in Table 2 was used as the host compound.
  • Comparative Examples 12 to 13 An organic EL device was produced in the same manner as in Example 1 except that only the second host shown in Table 2 was used as the host compound.
  • the evaluation results of the manufactured organic EL device are shown in Tables 1 and 2.
  • the brightness, drive voltage, power efficiency, and LT70 are the values at a drive current of 20 mA / cm 2 .
  • LT70 is the time required to attenuate from the luminance shown in Tables 1 and 2 to 70%, and represents the life characteristic.
  • the numbers of the first host and the second host are numbers with the above-mentioned exemplary compounds.
  • Table 3 lists the 50% weight loss temperatures (T 50 ) for compounds 1-15, 2-7, and 2-148.

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