WO2024171944A1 - 混合組成物及び有機電界発光素子 - Google Patents

混合組成物及び有機電界発光素子 Download PDF

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WO2024171944A1
WO2024171944A1 PCT/JP2024/004354 JP2024004354W WO2024171944A1 WO 2024171944 A1 WO2024171944 A1 WO 2024171944A1 JP 2024004354 W JP2024004354 W JP 2024004354W WO 2024171944 A1 WO2024171944 A1 WO 2024171944A1
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general formula
substituted
group
mixed composition
compound
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French (fr)
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満 坂井
智 浮海
鉄郎 山下
裕士 池永
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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 CN202480010935.XA priority patent/CN120660471A/zh
Priority to KR1020257030143A priority patent/KR20250151428A/ko
Publication of WO2024171944A1 publication Critical patent/WO2024171944A1/ja
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    • C07D209/82—Carbazoles; Hydrogenated carbazoles
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    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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Definitions

  • the present invention relates to a mixed composition and an organic electroluminescent device (referred to as an organic EL device) using the same. More specifically, the present invention relates to a mixed composition consisting of an indolocarbazole compound and a biscarbazole compound, and an organic EL device using the same.
  • an organic electroluminescent device When a voltage is applied to an organic electroluminescent device (referred to as an organic EL device), holes are injected from the anode and electrons are injected from the cathode into the light-emitting layer. In the light-emitting layer, the injected holes and electrons recombine to generate excitons. At this time, singlet excitons and triplet excitons are generated in a ratio of 1:3 according to the statistical law of electron spin. It is said that the internal quantum efficiency of a fluorescent organic EL device that uses light emission from singlet excitons is limited to 25%.
  • Patent Document 1 discloses an organic EL element utilizing the TTF (Triplet-Triplet Fusion) mechanism, which is one of the mechanisms of delayed fluorescence.
  • TTF Triplet-Triplet Fusion
  • the TTF mechanism utilizes the phenomenon in which singlet excitons are generated by the collision of two triplet excitons, and it is believed that the internal quantum efficiency can be theoretically increased to 40%.
  • Patent Document 2 discloses an organic EL element that utilizes the TADF (Thermally Activated Delayed Fluorescence) mechanism.
  • TADF Thermally Activated Delayed Fluorescence
  • the TADF mechanism utilizes the phenomenon in which reverse intersystem crossing occurs from triplet excitons to singlet excitons in a material with a small energy difference between the singlet level and the triplet level, and is believed to theoretically increase the internal quantum efficiency to 100%.
  • phosphorescent elements 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 Document 5 discloses the use of an indolocarbazole compound and a biscarbazole compound as a mixed host.
  • Patent Document 6 discloses the use of a deuterated indolocarbazole compound as a host material.
  • Patent documents 7, 8, and 9 disclose the use of a mixed composition of multiple indolocarbazole compounds and biscarbazole compounds as a host material.
  • Patent document 12 discloses the use of a molten mixture of indolocarbazole compounds and biscarbazole compounds, which are heated, melted, and mixed before deposition, as a host.
  • Patent documents 10 and 11 disclose the use of a mixed composition of multiple indolocarbazole compounds and deuterated biscarbazole compounds as a host material.
  • the present invention aims to provide a practically useful organic EL element that has high efficiency and a long life while requiring a low driving voltage, and a compound suitable for the same.
  • the present invention is a mixed composition containing a compound represented by general formula (1) and a compound represented by the following general formula (2).
  • ring A is a five-membered heterocycle represented by formula (1a) which is fused with two adjacent rings at any position.
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
  • Ar 3 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms, or a substituted or unsubstituted linking aromatic group in which 2 to 5 of these aromatic groups are linked, and when linked, the aromatic hydrocarbon groups or aromatic heterocyclic groups may be the same or different from each other.
  • R 1 's are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 12 carbon atoms, or a substituted or unsubstituted linked aromatic group in which 2 to 5 of these aromatic groups are linked together, and when linked, the aromatic hydrocarbon groups or aromatic heterocyclic groups may be the same or different.
  • a to d represent the number of substitutions, where a and c are each an integer from 0 to 4, b is an integer from 0 to 2, and d is an integer from 0 to 3, and preferably a and c are each an integer from 0 to 2, b is an integer from 0 to 1, and d is an integer from 0 to 1.
  • Ar 4 and Ar 5 each independently represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 14 carbon atoms, or a substituted or unsubstituted linked aromatic group formed by linking two of these aromatic hydrocarbon groups, and when linked, the aromatic hydrocarbon groups may be the same or different.
  • Ar 4 and Ar 5 are preferably a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted phenanthryl group, and more preferably an unsubstituted phenyl group.
  • L1 and L2 each independently represent a direct bond or a substituted or unsubstituted phenylene group.
  • L1 or L2 is not a direct bond, and the phenylene group is a trivalent phenylene group.
  • the mixed composition preferably contains 20 wt % or more and 70 wt % or less of the compound represented by general formula (1) relative to the total of the compound represented by general formula (1) and the compound represented by general formula (2).
  • the present invention is a mixed composition characterized by containing a compound represented by the general formula (1) as a first host and a compound represented by the general formula (2) as a second host.
  • the mixed composition includes a premix used as the mixed host and a mixture present in a vapor deposition film created using the mixed host.
  • the vapor deposition film includes a light-emitting layer having a dopant (light-emitting dopant material).
  • At least one of the compound represented by the general formula (1) and the compound represented by the general formula (2) preferably has some or all of its hydrogen atoms substituted with deuterium atoms.
  • at least one of the compounds represented by the general formula (1) and the general formula (2) has some or all of its hydrogen atoms substituted with deuterium, and the average deuteration rate is preferably 30% or more, and more preferably 40% or more.
  • the mixed composition is a material for manufacturing at least one layer of an organic electroluminescent device by a vapor deposition method, and may be a premixture that is mixed in advance before vapor deposition, or may be a premixture that is heated, melted, and mixed in advance before vapor deposition. In this premixture, it is preferable that the difference in 50% weight loss temperature between the compound represented by the general formula (1) and the compound represented by the general formula (2) is within 20°C.
  • the present invention also provides an organic electroluminescent device having multiple organic layers between an anode and a cathode, characterized in that at least one of the organic layers contains the above-mentioned mixed composition.
  • the organic layer containing the mixed composition is at least one layer selected from the group consisting of a light-emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer, and is more preferably a light-emitting layer.
  • the light-emitting layer preferably contains at least one light-emitting dopant, and more preferably contains a compound represented by the general formula (1) as a first host and a compound represented by the general formula (2) as a second host, and the light-emitting layer preferably contains at least one light-emitting dopant.
  • the present invention also provides a method for producing an organic electroluminescent device having multiple organic layers, including a light-emitting layer, between an anode and a cathode, the method comprising the steps of preparing the above-mentioned mixed composition and forming a light-emitting layer by depositing the mixed composition from a single deposition source.
  • the materials used in the organic layers must be highly resistant to electric charges, and it is particularly important to suppress the leakage of excitons and electric charges into the surrounding layers in the light-emitting layer. Improving the bias of the light-emitting region in the light-emitting layer is effective in suppressing this leakage of charge/excitons, and to do this it is necessary to control the amount of both electric charges (electrons/holes) injected into the light-emitting layer or the transportability of both electric charges in the light-emitting layer within a preferred range.
  • the charge injection and transport properties of the material used in the organic layer are largely influenced by the energy level of the molecular orbital of the material and the magnitude of the interaction between the molecules.
  • the mixed composition of the present invention since it contains an indolocarbazole compound having a carbazolyl group represented by formula (1a), it has a particularly high electron injection and transport property, but the steric hindrance effect of the carbazolyl group can prevent the indolocarbazole molecules from approaching each other.
  • the amount of charge injected into the organic layer can be adjusted more precisely than when each compound is used alone.
  • the minimum excited triplet energy is high enough to trap the excitation energy generated in the light-emitting layer, so there is no energy outflow from within the light-emitting layer, and high efficiency and a long life can be achieved at low voltage.
  • FIG. 1 is a cross-sectional view showing a structural example of an organic EL element.
  • the mixed composition of the present invention contains a compound represented by the general formula (1) and a compound represented by the general formula (2).
  • ring A is a five-membered heterocycle represented by formula (1a), which is fused to two adjacent rings at any position, but is not fused to a side containing N. Therefore, the indolocarbazole ring has several isomeric structures, but the number is limited.
  • the compound represented by general formula (1) has an embodiment represented by any one of the following formulas (3) to (8), preferably the formulas (6) to (8), and more preferably the structure represented by formula (8).
  • formulas (3) to (8) symbols common to general formula (1) have the same meanings.
  • the substitution position of the carbazolyl group on the indolocarbazole is preferably formula (9) to (11), more preferably formula (10) or (11).
  • symbols common to formula (1a) have the same meanings.
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group, and the sum of the numbers of benzene rings in Ar 1 and Ar 2 is preferably 4 or less, more preferably 3 or less.
  • a biphenyl group has a structure in which two benzene rings are linked
  • a terphenyl group has a structure in which three benzene rings are linked
  • the bonding position of each benzene ring may be any of o-, m-, or p-position. In addition, it may be linear or branched.
  • Ar3 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 17 carbon atoms, or a substituted or unsubstituted linked aromatic group in which 2 to 5 of these aromatic groups are linked together, and is preferably a substituted or unsubstituted aromatic hydrocarbon group having 6 to 12 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 11 carbon atoms, or a substituted or unsubstituted linked aromatic group in which 2 of these aromatic hydrocarbon groups are linked together.
  • unsubstituted aromatic hydrocarbon groups having 6 to 18 carbon atoms unsubstituted aromatic heterocyclic groups having 3 to 17 carbon atoms, or unsubstituted linked aromatic groups in which 2 to 5 of these aromatic groups are linked together
  • benzene pentalene, indene, naphthalene, anthracene, phenanthrene, pyrrole, imidazole, pyrazole, thiazole, thiophene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, isoindole, indazole, purine, benzimidazole, indolizine, chromene, benzoxazole, isobenzofuran, quinolizine, isoquinoline, imidazole, naphthyridine, phthalazine, These include quinazoline, quinoxaline, cinnoline, quinoline, pteridine, perim
  • Each R 1 is independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 12 carbon atoms, or a substituted or unsubstituted linked aromatic group in which 2 to 5 of these aromatic groups are linked, and when linked, the aromatic hydrocarbon groups or aromatic heterocyclic groups may be the same or different from each other.
  • a substituted or unsubstituted phenyl group is preferable.
  • a linking aromatic group refers to an aromatic group in which the aromatic rings of two or more aromatic groups are linked by single bonds. These linking aromatic groups may be linear or branched. The linking position when the benzene rings are linked together may be ortho, meta, or para, with para- or meta-linking being preferred.
  • the aromatic group may be an aromatic hydrocarbon group or an aromatic heterocyclic group, and the multiple aromatic groups may be the same or different.
  • R 1 which is an unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms, an unsubstituted aromatic heterocyclic group having 3 to 12 carbon atoms, or an unsubstituted linked aromatic group in which 2 to 5 of these aromatic groups are linked together
  • the aromatic hydrocarbon group, aromatic heterocyclic group, or linking aromatic group may each have a substituent.
  • the substituent is preferably deuterium, halogen, 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, or a diarylamino group having 12 to 44 carbon atoms.
  • the substituent is an aliphatic hydrocarbon group having 1 to 10 carbon atoms, it may be linear, branched, or cyclic.
  • the triarylsilyl group or the diarylamino group is a substituent of the aromatic hydrocarbon group, aromatic heterocyclic group, or linking aromatic group, silicon and carbon, or nitrogen and carbon, are bonded by a single bond, respectively.
  • the number of the above-mentioned substituents is preferably 0 to 5, and more preferably 0 to 2.
  • the aromatic hydrocarbon group and aromatic heterocyclic group have a substituent, the number of carbon atoms is calculated not including the number of carbon atoms of the substituent. However, it is preferable that the total number of carbon atoms including the number of carbon atoms of the substituent falls within the above range.
  • substituents include deuterium, cyano, methyl, ethyl, propyl, i-propyl, butyl, t-butyl, pentyl, neopentyl, cyclopentyl, hexyl, cyclohexyl, heptyl, octyl, nonyl, decyl, vinyl, propenyl, butenyl, pentenyl, methoxy, ethoxy, propoxy, butoxy, pentoxy, diphenylamino, naphthylphenylamino, dinaphthylamino, dianthranylamino, diphenanthrenylamino, dipyrenylamino, etc.
  • the number of substitutions of n of the substituted deuterium (D) means an average number independently for each compound, and changes depending on the average deuteration rate.
  • compounds 101, 102, 103, 109, 110, 111, 124, 127, 130, 136, 137, 138, 144, 145, 146, 159, 162, 165, 171, 172, 173, 179, 180, 181, 194, 197, and 200 are preferred.
  • Ar 4 and Ar 5 each independently represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 14 carbon atoms, or a substituted or unsubstituted linked aromatic group formed by linking two of these aromatic hydrocarbon groups.
  • it is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 10 carbon atoms, or a substituted or unsubstituted linked aromatic group formed by linking two of these aromatic hydrocarbon groups.
  • a biphenyl group has a structure in which two benzene rings are linked, and the bonding position of each benzene ring may be any of o-, m-, and p-positions.
  • the aromatic hydrocarbon groups linked to the above-mentioned linked aromatic groups may be the same or different.
  • specific examples of the unsubstituted aromatic hydrocarbon group having 6 to 14 carbon atoms or the unsubstituted linked aromatic group formed by linking two of these aromatic groups include benzene, naphthalene, phenanthrene, and groups derived from a compound formed by linking two of these.
  • L1 and L2 each represent a direct bond or a substituted or unsubstituted phenylene group, which may be ortho-, meta-, or para-bonded.
  • Each of y and z represents the number of substitutions, and independently represents 1 or 2, preferably 1.
  • L1 or L2 is a trivalent phenylene group.
  • the formula (12) is preferable.
  • the symbols common to the general formula (2) have the same meanings.
  • the hydrogen in the compound contained in the mixed composition of the present invention may be deuterium. That is, in general formula (1), the hydrogen of the fused ring (indolocarbazole ring) containing ring A, the hydrogen of the group or carbazolyl group substituted on the indolocarbazole ring, the hydrogen of the aromatic rings of Ar 1 , Ar 2 , Ar 3 , and R 1 , and the hydrogen of the substituents substituted on these aromatic rings may be part or all deuterium.
  • the hydrogen of the two carbazole rings in the compound represented by general formula (2), the hydrogen of the aromatic rings of Ar 4 , Ar 5 , L 1 , and L 2 , and the hydrogen of the substituents of Ar 4 , Ar 5 , L 1 , and L 2 may be part or all deuterium.
  • the compounds represented by general formula (1) or general formula (2) include both a single compound and a mixture of two or more compounds. That is, the compounds represented by general formula (1) or general formula (2) may be two or more compounds included in these formulas, or may be a mixture of compounds with different deuteration numbers or deuteration positions. In addition, all of the compounds contained in the mixed composition may be deuterated, or only a portion of the compounds may be deuterated.
  • the compounds represented by general formula (1) or (2) each independently have an average deuteration rate of preferably 30% or more, more preferably 40% or more, and further preferably 50% or more.
  • an average deuteration rate of 50% means that on average half of all hydrogen atoms are replaced with deuterium atoms.
  • the average deuteration ratio can be determined by mass spectrometry or proton nuclear magnetic resonance spectroscopy. For example, when determining by proton nuclear magnetic resonance spectroscopy, a measurement sample is first prepared by adding and dissolving the compound and an internal standard in a heavy solvent, and the proton concentration [mol/g] of the compound contained in the measurement sample is calculated from the integrated intensity ratio from the internal standard and the compound. Next, the ratio of the proton concentration of the deuterated compound to the proton concentration of the corresponding non-deuterated compound is calculated, and the average deuteration ratio of the deuterated compounds can be calculated by subtracting it from 1.
  • the mixed composition of the present invention contains a compound represented by the general formula (1) and a compound represented by the general formula (2), and the mixing ratio (weight ratio) of the compound represented by the general formula (1) is preferably 20 to 70 wt %, more preferably 30 to 60 wt %, and even more preferably 40 to 50 wt %, of the total of the two.
  • the mixed composition may contain other compounds in addition to the compound represented by general formula (1) and the compound represented by general formula (2).
  • the other compounds may include known host materials and luminescent dopants.
  • the compound represented by general formula (1) and the compound represented by general formula (2) should be 50 wt% or more of the total, and more preferably 75 wt% or more.
  • the mixed composition of the present invention is suitable as a material or component of an organic EL device.
  • the mixed composition is used as a component of an organic EL device, it is contained in an organic layer of the organic EL device, and this organic layer is preferably selected from the group consisting of a light-emitting layer, a hole-injection layer, a hole-transport layer, an electron-transport layer, an electron-injection layer, a hole-blocking layer, and an electron-blocking layer, and is preferably a light-emitting layer, and the light-emitting layer preferably contains at least one light-emitting dopant.
  • the light-emitting layer contains the mixed composition of the present invention
  • the light-emitting layer contains the mixed composition as a host.
  • the compound represented by the general formula (1) is used as the first host
  • the compound represented by the general formula (2) is used as the second host.
  • the mixed composition of the present invention When the mixed composition of the present invention is used as a component of an organic EL device, a method of vapor-depositing a plurality of compounds such as the compound represented by the general formula (1) and the compound represented by the general formula (2) individually from different vapor deposition sources can be adopted. However, it is preferable to premix the compounds before vapor deposition to prepare a premixture, and then simultaneously evaporate and vapor-deposit the premixture from one vapor deposition source to form an organic layer, preferably a light-emitting layer. When the above premix is used as the mixed composition of the present invention to form a light-emitting layer, a necessary light-emitting dopant material or other hosts to be used as necessary may be mixed therein. However, when there is a large difference in the temperature at which the desired vapor pressure is obtained, it is preferable to deposit the light-emitting dopant material and other hosts from different deposition sources.
  • the mixed composition of the present invention is the above-mentioned preliminary mixture, in order to perform stable deposition, it is desirable that the compound represented by the general formula (1) and the compound represented by the general formula (2) have a 50% weight loss temperature within 20°C. More preferably, it is within 15°C.
  • the organic EL element of the present invention has a plurality of organic layers between opposing electrodes, and at least one of the organic layers is an emitting layer. At least one of the emitting layers preferably contains the mixed composition as a host. When the emitting layer contains the mixed composition, it preferably contains at least one luminescent dopant.
  • FIG. 1 is a cross-sectional view showing an example of the structure of a general organic EL element 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, 5 is a light-emitting layer, 6 is an electron transport layer, and 7 is a cathode.
  • the organic EL element of the present invention may have an exciton blocking layer adjacent to the light-emitting layer, or 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 at the same time.
  • the organic EL element of the present invention has an anode, a light-emitting layer, and a cathode as essential layers, but may have a hole injection transport layer and an electron injection transport layer in addition to the essential layers, and may further have a hole blocking layer between the light-emitting layer and the electron injection transport layer.
  • the hole injection transport layer means either the hole injection layer or the hole transport layer, or both
  • the electron injection transport layer means either the electron injection layer or the electron transport layer, or both.
  • the organic EL element of the present invention is preferably supported by a substrate.
  • a substrate There are no particular limitations on the substrate, and any substrate that has been conventionally used in organic EL elements, such as glass, transparent plastic, quartz, etc., can be used.
  • anode material in the organic EL element a material consisting of a metal, alloy, electrically conductive compound, or a mixture thereof having a large work function (4 eV or more) is preferably used.
  • electrode materials include metals such as Au, CuI, indium tin oxide (ITO), SnO 2 , ZnO, and other conductive transparent materials.
  • amorphous materials such as IDIXO (In2O3-ZnO) that can form a transparent conductive film may be used.
  • the anode may be formed by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering, and forming a pattern of a desired shape by a photolithography method, or when pattern accuracy is not required very much (about 100 ⁇ m or more), a pattern may be formed through a mask of a desired shape during vapor deposition or sputtering of the electrode material.
  • a coatable material such as an organic conductive compound
  • a wet film formation method such as a printing method or a coating method may be used.
  • the sheet resistance of the anode is preferably several hundred ⁇ / ⁇ or less.
  • the film thickness depends on the material, but is usually selected from the range of 10 to 1000 nm, preferably 10 to 200 nm.
  • the cathode material a material consisting of a metal (electron injecting metal), an alloy, an electrically conductive compound, or a mixture thereof having a small work function (4 eV or less) is used.
  • electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, a magnesium/copper mixture, a magnesium/silver mixture, a magnesium/aluminum mixture, a magnesium/indium mixture, an aluminum/aluminum oxide (Al 2 O 3 ) mixture, indium, a lithium/aluminum mixture, and a rare earth metal.
  • a mixture of an electron injecting metal and a second metal having a larger and more stable work function than the electron injecting metal such as a magnesium/silver mixture, a magnesium/aluminum mixture, a magnesium/indium mixture, an aluminum/aluminum oxide mixture, a lithium/aluminum mixture, and aluminum, is preferred.
  • the cathode can be produced by forming a thin film of these cathode materials by a method such as 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 anode or the cathode of the organic EL element is transparent or semi-transparent in order to transmit the emitted light, the luminance of the emitted light is improved, which is advantageous.
  • a transparent or translucent cathode can be made by forming the conductive transparent material mentioned in the explanation of the anode on top of it. By applying this, it is possible to make an element in which both the anode and cathode are optically 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 cathode, respectively, and contains a light-emitting dopant material and a host.
  • the mixed composition of the present invention can be suitably used as a material for organic electroluminescent devices, and can preferably be used as a host. It is preferable to use a compound represented by general formula (1) as the first host and a compound represented by general formula (2) as the second host. One type of the first host or second host may be used, or two or more different compounds may be used. If necessary, one or more other known host materials may be used in combination, but the amount used should be 50 wt % or less, preferably 25 wt % or less, based on the total host materials.
  • the method for producing an organic electroluminescent device of the present invention includes the steps of preparing the above premixture and depositing the premixture from a single deposition source to form a light-emitting layer.
  • a more preferable method is to vaporize and deposit the premixture from a single deposition source.
  • the premixture 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 reduced pressure (1 Pa) of nitrogen gas flow. It is believed that vaporization by evaporation or sublimation occurs most actively around this temperature.
  • the difference in the 50% weight loss temperature is preferably within 20°C, because a uniform deposition film can be obtained when this premix is vaporized from a single deposition source and deposited.
  • the premix may be mixed with a luminescent dopant material required to form a light-emitting layer or other hosts to be used as necessary.
  • a method capable of mixing the first host and the second host as uniformly as possible is preferable, and examples of the method include pulverization and mixing, sublimation, etc. Also included is a method in which a mixture containing the first host and the second host is heated to a temperature equal to or higher than the melting point of both or one of the first host and the second host under reduced pressure, for example, a reduced pressure of 200 Pa or less, or under an inert gas atmosphere such as nitrogen, to melt the mixture, but the method is not limited to these methods.
  • the premix may be in a molten state, but it is preferable to use a mixture obtained by cooling and solidifying the molten mixture.
  • the premix may be in the form of a powder, stick, or granules.
  • known methods include a method of producing the compound using a fully or partially deuterated starting material, and a method of producing the compound by a hydrogen/deuterium exchange reaction.
  • the fully or partially deuterated starting material can be purchased from a commercial source or produced by a known hydrogen/deuterium exchange reaction.
  • Known hydrogen/deuterium exchange reactions include a method in which a non-deuterated product is subjected to deuterium gas or its equivalent in the presence of a transition metal catalyst, and a method in which a non-deuterated product is treated with a deuterated solvent (such as deuterated benzene) in the presence of an acid catalyst.
  • the phosphorescent dopant when used as the luminescent dopant material, the phosphorescent dopant preferably contains an organometallic complex containing at least one metal selected from ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum, and gold.
  • the iridium complexes described in J.Am.Chem.Soc.2001,123,4304, JP2013-530515A, US2016/0049599A, US2017/0069848A, US2018/0282356A, or US2019/0036043A, or the platinum complexes described in US2018/0013078A or KR2018-094482A, are preferably used, but are not limited to these.
  • the light-emitting layer may contain only one type of phosphorescent dopant material, or may contain two or more types.
  • the content of the phosphorescent dopant material is preferably 0.1 to 30 wt % relative to the host material, and more preferably 1 to 20 wt %.
  • Phosphorescent dopant materials are not particularly limited, but specific examples include the following compounds:
  • fluorescent dopant examples include, but are not limited to, benzoxazole derivatives, benzothiazole derivatives, benzimidazole derivatives, styrylbenzene derivatives, polyphenyl derivatives, diphenylbutadiene derivatives, tetraphenylbutadiene derivatives, naphthalimide derivatives, coumarin derivatives, condensed aromatic compounds, perinone derivatives, oxadiazole derivatives, oxazine derivatives, aldazine derivatives, pyrrolidine derivatives, cyclopentadiene derivatives, bisstyrylanthracene derivatives, quinacridone derivatives, pyrrolopyridine derivatives, thiadiazolopyridine derivatives, styrylamine derivatives, diketopyrrolopyrrole derivatives, aromatic dimethylidine compounds, various metal complexes such as metal complexes of 8-quinol
  • thermally activated delayed fluorescent dopant When a thermally activated delayed fluorescent dopant is used as the luminescent dopant material, examples of the thermally activated delayed fluorescent dopant include, but are not limited to, metal complexes such as tin complexes and copper complexes, indolocarbazole derivatives described in WO2011/070963A, cyanobenzene derivatives and carbazole derivatives described in Nature 2012,492,234, phenazine derivatives, oxadiazole derivatives, triazole derivatives, sulfone derivatives, phenoxazine derivatives and acridine derivatives described in Nature Photonics 2014,8,326, etc.
  • metal complexes such as tin complexes and copper complexes
  • indolocarbazole derivatives described in WO2011/070963A cyanobenzene derivatives and carbazole derivatives described in Nature 2012,492,234, phenazine derivatives, oxadiazole derivatives
  • the thermally activated delayed fluorescent dopant material is not particularly limited, but specific examples thereof include the following compounds.
  • the light-emitting layer may contain only one type of thermally activated delayed fluorescent dopant material, or may contain two or more types.
  • the thermally activated delayed fluorescent dopant may be mixed with a phosphorescent dopant or a fluorescent dopant.
  • the content of the thermally activated delayed fluorescent dopant material is preferably 0.1 to 50 wt %, and more preferably 1 to 30 wt %, relative to the host material.
  • the injection layer is a layer provided between an electrode and an organic layer to reduce the driving voltage and improve the luminance of light emitted, and includes a hole injection layer and an electron injection layer, and may be provided between the anode and the light emitting layer or the hole transport layer, and between the cathode and the light emitting layer or the electron transport layer.
  • the injection layer can be provided as necessary.
  • a hole blocking layer in a broad sense, has the function of an electron transport layer and is made of a hole blocking material that has the function of transporting electrons but has an extremely low ability to transport holes, and by transporting electrons while blocking holes, it is possible to improve the probability of recombination of electrons and holes in the light-emitting layer.
  • the electron blocking layer functions as a hole transport layer, and can increase the probability of recombination of electrons and holes in the light emitting layer by blocking electrons while transporting holes.
  • the electron blocking layer may be made of a known material, or may be made of a material for the hole transport layer, as described below, if necessary.
  • the thickness of the electron blocking layer is preferably 3 to 100 nm, and more preferably 5 to 30 nm.
  • the exciton blocking layer is a layer for preventing excitons generated by the recombination of holes and electrons in the light-emitting layer from diffusing into the charge transport layer, and the insertion of this layer makes it possible to efficiently confine excitons in the light-emitting layer, thereby improving the luminous efficiency of the device.
  • the exciton blocking layer can be inserted between two adjacent light-emitting layers.
  • the material for the exciton blocking layer can be any known exciton blocking layer material. Examples include 1,3-dicarbazolylbenzene (mCP) and bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum(III) (BAlq).
  • mCP 1,3-dicarbazolylbenzene
  • BAlq bis(8-hydroxy-2-methylquinoline)-(4-phenylphenoxy)aluminum(III)
  • 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 multiple layers.
  • the hole transport material is one that has either hole injection or transport properties or electron barrier properties, and may be either organic or inorganic. Any of the conventionally known compounds may be selected and used for the hole transport layer. 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, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline-based copolymers, and conductive polymer oligomers, particularly thiophene oligomers, etc., but it is preferable to use porphyrin derivatives, arylamine derivatives, and styrylamine derivative
  • the electron transport layer is made of a material having a function of transporting electrons, and the electron transport layer may be provided as a single layer or as a multi-layer.
  • the electron transport material (which may also serve as a hole blocking material) may have the function of transmitting electrons injected from the cathode to the light emitting layer.
  • any compound selected from conventionally known compounds may be used, such as polycyclic aromatic derivatives such as naphthalene, anthracene, and phenanthroline, tris(8-hydroxyquinoline)aluminum(III) derivatives, phosphine oxide derivatives, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, bipyridine derivatives, quinoline derivatives, oxadiazole derivatives, benzimidazole derivatives, benzothiazole derivatives, and indolocarbazole derivatives.
  • polymeric materials in which these materials are introduced into the polymer chain or in which these
  • reaction solution was added to a deuterated water solution (200 mL) of sodium carbonate (7.4 g) and quenched, and the product was separated and purified to obtain 2.5 g (4.25 mmol, 29% yield) of compound (601) as a white solid (APCI-TOFMS, m/z 589[M+H]+).
  • the average deuteration ratio of compound 601 obtained in the above Synthesis Example 4 was determined by proton nuclear magnetic resonance spectroscopy.
  • a measurement sample was prepared by dissolving compound 601 (5.0 mg) and dimethyl sulfone (2.0 mg) as an internal standard in deuterated tetrahydrofuran (1.0 ml).
  • the average proton concentration [mol/g] of compound 601 contained in the measurement sample was calculated from the integrated intensity ratio of the internal standard and compound 601.
  • the average proton concentration [mol/g] of the non-deuterated form of compound 601 (compound 502) was also calculated in the same manner.
  • the average deuteration rate of compound 407 was determined by proton nuclear magnetic resonance spectroscopy.
  • a measurement sample was prepared by dissolving compound 136 (5.0 mg) and dimethyl sulfone (2.0 mg) as an internal standard in deuterated tetrahydrofuran (1.0 ml).
  • the average proton concentration [mol/g] of compound 407 contained in the measurement sample was calculated from the integrated intensity ratio of the internal standard and compound 407.
  • the average proton concentration [mol/g] of the non-deuterated form of compound 407 (compound 136) was also calculated in the same manner.
  • the ratio of the proton concentration of compound 407 to the proton concentration of compound 136 was calculated, and the average deuteration rate of compound 407 was calculated to be 52.1% by subtracting it from 1.
  • Example 1 Each thin film was laminated by vacuum deposition at a vacuum degree of 4.0 ⁇ 10 ⁇ 5 Pa on a glass substrate on which an anode made of ITO with a thickness of 110 nm had been formed.
  • compound A and compound B were co-deposited from different deposition sources on ITO to form a hole injection layer with a thickness of 10 nm. At this time, the co-deposition was performed under deposition conditions such that the concentration of compound B was 3 wt %.
  • compound A was formed as a first hole transport layer to a thickness of 110 nm.
  • compound C was formed as a second hole transport layer to a thickness of 10 nm.
  • compound D was formed to a thickness of 5 nm as an electron blocking layer.
  • Compound 136 (first host) and Compound 502 (second host) were weighed out as hosts in the weight ratio shown in Table 2, and mixed while grinding in a mortar to form a preliminary mixture, which was evaporated from a single evaporation source, and Compound E was evaporated as an emitting dopant from a different evaporation source to form an emitting layer having a thickness of 40 nm by co-evaporation under evaporation conditions where the concentration of Compound E was 15 wt % and the weight ratio of the first host to the second host was 30:70.
  • compound F was formed to a thickness of 5 nm as a hole blocking layer.
  • compound G was formed as an electron transport layer to a thickness of 30 nm.
  • LiF was formed as an electron injection layer to a thickness of 1 nm on the electron transport layer.
  • an Al film was formed as a cathode with a thickness of 70 nm on the electron injection layer to complete an organic EL device.
  • Examples 2 to 27, Comparative Examples 1 to 9 An organic EL device was prepared in the same manner as in Example 1 except that the compounds shown in Tables 2 and 3 were used as the first host and the second host in the weight ratios shown in Tables 2 and 3.
  • the evaluation results of the prepared organic EL device are shown in Tables 2 and 3.
  • the luminance, voltage, and current efficiency are values at a driving current of 10 mA/ cm2 , which are initial characteristics.
  • LT70 is the time required for the luminance to decay to 70% when driven at an initial luminance of 9000 nits, and represents the life characteristics.
  • the numbers of the first host and the second host are the numbers given to the above exemplary compounds, and the weight ratio is first host:second host. All characteristics are expressed as relative values with the characteristics of Comparative Example 1 taken as 100%.
  • Examples 28 to 54, Comparative Examples 10 to 18 An organic EL device was prepared in the same manner as in Example 1, except that the compounds shown in Tables 4 and 5 were used as the first host and the second host and were co-deposited from different deposition sources in the weight ratios shown in Tables 4 and 5.
  • Examples 55 to 87, Comparative Examples 19 to 27 An organic EL device was produced in the same manner as in Example 1, except that the compounds shown in Tables 6 and 7 were used as the first host and the second host, and the compounds were weighed out in the weight ratios shown in Tables 6 and 7, and mixed in a mortar while being ground. The mixture was placed in a vacuum chamber and heated to 320° C. under a reduced pressure of 100 Pa or less to melt the mixture, and then cooled to room temperature. The mixture was ground and mixed to obtain a preliminary mixture, which was then evaporated from a single evaporation source.
  • Examples 1 to 87 have improved efficiency and good characteristics while having the same or better life characteristics as the comparative examples.
  • efficiency and life may be in a trade-off relationship, and it is difficult to improve both current efficiency and life characteristics.
  • improving current efficiency leads to lower power consumption and improved luminance, so if current efficiency can be improved while maintaining a certain degree of life characteristics, a more practical element can be obtained.
  • a current efficiency of 110% or more can be achieved by combining materials and mixing ratios while maintaining a life characteristic of about 105% or exhibiting a life characteristic of 110% or more compared to the cases of Comparative Examples 1, 10, and 19 in which a conventional compound was used as part of the mixed host material, and an organic EL element advantageous for practical use can be obtained.
  • Table 8 lists the 50% weight loss temperatures (T50) for compounds 508, 605, 502, 601, 607, 136, 407, 171, 413, 207, 429, H, I, J, and K.

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