WO2015098975A1 - 有機エレクトロルミネッセンス素子および電子機器 - Google Patents

有機エレクトロルミネッセンス素子および電子機器 Download PDF

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WO2015098975A1
WO2015098975A1 PCT/JP2014/084175 JP2014084175W WO2015098975A1 WO 2015098975 A1 WO2015098975 A1 WO 2015098975A1 JP 2014084175 W JP2014084175 W JP 2014084175W WO 2015098975 A1 WO2015098975 A1 WO 2015098975A1
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group
substituted
unsubstituted
carbon atoms
ring
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English (en)
French (fr)
Japanese (ja)
Inventor
俊成 荻原
圭 吉田
亮平 橋本
由美子 水木
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Idemitsu Kosan Co Ltd
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Idemitsu Kosan Co Ltd
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=53478824&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO2015098975(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority to KR1020197019230A priority Critical patent/KR20190083000A/ko
Priority to KR1020157025439A priority patent/KR101831211B1/ko
Priority to EP21152571.2A priority patent/EP3879592B1/en
Priority to EP14874936.9A priority patent/EP2958158B1/en
Priority to US14/777,679 priority patent/US9905779B2/en
Application filed by Idemitsu Kosan Co Ltd filed Critical Idemitsu Kosan Co Ltd
Priority to CN201480017162.4A priority patent/CN105103326B/zh
Priority to KR1020187004541A priority patent/KR101997907B1/ko
Publication of WO2015098975A1 publication Critical patent/WO2015098975A1/ja
Anticipated expiration legal-status Critical
Priority to US15/866,616 priority patent/US10811616B2/en
Priority to US17/009,059 priority patent/US11569456B2/en
Priority to US18/069,244 priority patent/US20230126981A1/en
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Definitions

  • the present invention relates to an organic electroluminescence element and an electronic device.
  • an organic electroluminescence element (hereinafter sometimes referred to as an organic EL element)
  • holes from the anode and electrons from the cathode are injected into the light emitting layer.
  • the injected holes and electrons are recombined to form excitons.
  • singlet excitons and triplet excitons are generated at a ratio of 25%: 75% according to the statistical rule of electron spin.
  • a fluorescence type organic EL device using light emitted from singlet excitons is said to have a limit of 25% internal quantum efficiency.
  • TADF Thermally Activated Delayed Fluorescence, heat activated delayed fluorescence
  • ⁇ ST small energy difference
  • ⁇ ST small energy difference
  • Patent Documents 1 to 3 disclose organic EL elements using the TADF mechanism.
  • Patent Document 1 discloses an organic EL element including a light-emitting layer containing a compound having a small ⁇ ST as a host material and a fluorescent compound as a dopant material. According to Patent Document 1, it is described that the internal quantum efficiency is improved by using a compound having a small ⁇ ST as a host material and expressing the TADF mechanism in the host material.
  • Patent Document 2 and Patent Document 3 also disclose an organic EL device including a light emitting layer containing a specific compound as a host material and a fluorescent compound as a dopant material. According to Patent Document 2 and Patent Document 3, as in Patent Document 1, the TADF mechanism is used to improve the performance of the organic EL element.
  • An object of the present invention is to provide an organic electroluminescence device capable of improving luminous efficiency. Another object of the present invention is to provide an electronic device provided with the organic electroluminescence element.
  • An organic electroluminescence device includes an anode, a light emitting layer, and a cathode, and the light emitting layer includes a first material, a second material, and a third material, One material is a fluorescent material, and the second material is a delayed fluorescent material, and the singlet energy of the third material is the singlet energy of the second material. Bigger than.
  • An electronic apparatus includes the organic electroluminescence element according to one embodiment of the present invention described above.
  • an organic electroluminescence element capable of improving luminous efficiency.
  • the organic EL element includes an organic layer between a pair of electrodes. This organic layer is formed by laminating a plurality of layers composed of organic compounds.
  • the organic layer may further contain an inorganic compound.
  • at least one of the organic layers is a light emitting layer. Therefore, the organic layer may be composed of, for example, a single light emitting layer, and is employed in organic EL elements such as a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and a barrier layer. It may have a layer.
  • the organic EL element 1 includes a translucent substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4.
  • the organic layer 10 includes a light emitting layer 5, a hole injection / transport layer 6 provided between the light emitting layer 5 and the anode 3, and an electron injection / transport layer provided between the light emitting layer 5 and the cathode 4. 7
  • the light emitting layer 5 contains a first material, a second material, and a third material.
  • the light emitting layer 5 may contain a phosphorescent metal complex.
  • the organic EL element of this embodiment even if the light emitting layer 5 does not contain a phosphorescent metal complex, it is possible to obtain a light emitting performance that exceeds that of a conventional fluorescent organic EL element.
  • hole injection / transport layer means “at least one of a hole injection layer and a hole transport layer”.
  • Electro injection / transport layer means “at least one of an electron injection layer and an electron transport layer”.
  • the positive hole injection layer is provided between the anode and the positive hole transport layer.
  • each of the hole injection layer, the hole transport layer, the electron transport layer, and the electron injection layer may be formed of a single layer, or a plurality of layers may be stacked.
  • the 1st material which concerns on this embodiment is a luminescent material of fluorescence emission.
  • the first material need not be particularly limited in emission color, but preferably exhibits fluorescence with a main peak wavelength of 550 nm or less, and more preferably exhibits fluorescence with a main peak wavelength of 480 nm or less.
  • the organic EL element of the present embodiment is considered to emit blue light with higher light emission efficiency.
  • the main peak wavelength is the emission spectrum that maximizes the emission intensity in the measured emission spectrum of a toluene solution in which the first material is dissolved at a concentration of 10 ⁇ 5 mol / liter to 10 ⁇ 6 mol / liter.
  • the first material preferably exhibits blue fluorescence.
  • a 1st material is a material with a high fluorescence quantum yield.
  • Fluorescent material can be used as the first material according to this embodiment.
  • the fluorescent material include bisarylaminonaphthalene derivatives, aryl-substituted naphthalene derivatives, bisarylaminoanthracene derivatives, aryl-group-substituted anthracene derivatives, bisarylaminopyrene derivatives, aryl-group-substituted pyrene derivatives, bis Arylaminochrysene derivatives, aryl-substituted chrysene derivatives, bisarylaminofluoranthene derivatives, aryl-substituted fluoranthene derivatives, indenoperylene derivatives, acenaphthofluoranthene derivatives, pyromethene boron complex compounds, compounds having a pyromethene skeleton, having a pyromethene skeleton Examples thereof include metal complexes of compounds, diketopyrrolopyr
  • AD is a substituted or unsubstituted aromatic hydrocarbon group having 12 to 50 ring carbon atoms.
  • aromatic hydrocarbon group having 12 to 50 ring carbon atoms in AD include naphthalene, anthracene, benzoanthracene, phenanthrene, chrysene, pyrene, fluoranthene, benzofluoranthene, perylene, picene, triphenylene, fluorene, Examples include groups derived from benzofluorene, stilbene, naphthacene, acenaphthofluoranthene, and the like.
  • AD examples include a group obtained by benzoating an aromatic hydrocarbon group having 12 to 50 ring carbon atoms, and a group obtained by ring expansion.
  • BD is a group represented by the following general formula (11).
  • pa is an integer of 1 to 4
  • pb is an integer of 0 to 4.
  • Ar 1 , Ar 2 and Ar 3 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms, a substituted or unsubstituted carbon number of 1 to A substituent selected from the group consisting of 50 alkyl groups, substituted or unsubstituted alkenyl groups, substituted or unsubstituted alkynyl groups, and substituted or unsubstituted heterocyclic groups having 5 to 50 ring atoms;
  • pc is an integer of 0 or more and 4 or less, and in the general formula (11), the wavy line part represents the bonding site with the aromatic hydrocarbon group represented by AD .
  • Examples of the compound represented by the general formula (10) include compounds having the following general formulas, but the first material is not limited to these examples.
  • a D1 to A D4 are each independently synonymous with A D
  • B D1 to B D4 are each independently synonymous with BD .
  • the aromatic hydrocarbon group in AD is preferably an aromatic hydrocarbon group having 12 to 30 ring carbon atoms, more preferably an aromatic hydrocarbon group having 12 to 24 ring carbon atoms, Aromatic hydrocarbon groups having 18 to 20 carbon atoms are more preferred.
  • Examples of the aromatic hydrocarbon group in AD include naphthylphenyl group, naphthyl group, acenaphthylenyl group, anthryl group, benzoanthryl group, aceanthryl group, phenanthryl group, benzo [c] phenanthryl group, phenalenyl group, and fluorenyl.
  • aromatic hydrocarbon group in A D anthryl group, picenyl group, a pyrenyl group, a fluoranthenyl group, a benzo [k] fluoranthenyl group, benzofluorenyl group, styryl phenyl group, naphthacenyl group
  • a perylenyl group and a group obtained by further benzoating or ring-expanding them are preferable.
  • the aromatic hydrocarbon group in Ar 1 , Ar 2 and Ar 3 (hereinafter sometimes referred to as an aryl group) is independently an aromatic hydrocarbon group having 6 to 24 ring carbon atoms.
  • An aromatic hydrocarbon group having 6 to 12 ring carbon atoms is more preferable.
  • Examples of the aromatic hydrocarbon group in Ar 1 , Ar 2 and Ar 3 are each independently a phenyl group, a naphthylphenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, an acenaphthylenyl group, an anthryl group, or a benzoanthryl group.
  • a phenyl group, a biphenylyl group, a terphenylyl group, and a naphthyl group are preferable, a phenyl group, a biphenylyl group, and
  • aromatic hydrocarbon group having a substituent examples include phenyl naphthyl group, naphthylphenyl group, tolyl group, xylyl group, silylphenyl group, trimethylsilylphenyl group, 9,9-dimethylfluorenyl group, 9,9- And a diphenylfluorenyl group, a 9,9′-spirobifluorenyl group, a cyanophenyl group, and the like.
  • a tolyl group, a xylyl group, a trimethylsilylphenyl group, a 9,9-dimethylfluorenyl group, 9,9 -Diphenylfluorenyl group, 9,9'-spirobifluorenyl group, cyanophenyl group, silylphenyl group and the like are preferable.
  • an alkyl group having 1 to 10 carbon atoms is preferable, and an alkyl group having 1 to 5 carbon atoms is more preferable.
  • the alkyl group in Ar 1 and Ar 2 include a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group (isomer) Hexyl group (including isomers), heptyl group (including isomers), octyl group (including isomers), nonyl group (including isomers), decyl group (including isomers), And undecyl group (including isomers), dodecyl group (including isomers), and the like, such as methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group
  • the alkyl group in Ar 1 , Ar 2 and Ar 3 may be each independently a cycloalkyl group having 3 to 50 ring carbon atoms.
  • the cycloalkyl groups in Ar 1 , Ar 2 and Ar 3 are each independently preferably a cycloalkyl group having 3 to 6 ring carbon atoms, more preferably a cycloalkyl group having 5 or 6 ring carbon atoms. .
  • Examples of the cycloalkyl group in Ar 1 , Ar 2 and Ar 3 include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, and the like. And a cyclohexyl group is preferred.
  • the alkenyl groups in Ar 1 , Ar 2 and Ar 3 are each independently preferably an alkenyl group having 2 to 20 carbon atoms, and more preferably an alkenyl group having 2 to 10 carbon atoms.
  • Examples of the alkenyl group in Ar 1 , Ar 2 and Ar 3 include a vinyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1,3-butanedienyl group, and a 1-methylvinyl group.
  • Examples of the substituted alkenyl group include a styryl group, 2,2-diphenylvinyl group, 1,2-diphenylvinyl group, 1-phenylallyl group, 2-phenylallyl group, 3-phenylallyl group, 3,3- Examples thereof include a diphenylallyl group, a 1-phenyl-1-butenyl group, and a 3-phenyl-1-butenyl group.
  • the alkynyl group for Ar 1 , Ar 2 and Ar 3 an alkynyl group having 2 to 20 carbon atoms is preferable, and an alkynyl group having 2 to 10 carbon atoms is more preferable.
  • Examples of the alkynyl group in Ar 1 , Ar 2 and Ar 3 include a propargyl group and a 3-pentynyl group.
  • a heterocyclic group having 5 to 24 ring atoms is preferably independently selected, and a heterocyclic group having 5 to 18 ring atoms is preferable. More preferred.
  • the heterocyclic group in Ar 1 , Ar 2 and Ar 3 include heterocyclic groups containing 1 to 5 heteroatoms.
  • the hetero atom include a nitrogen atom, an oxygen atom, and a sulfur atom.
  • heterocyclic groups in Ar 1 , Ar 2 and Ar 3 are each independently, for example, pyrrolyl group, furyl group, thienyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, imidazolyl group , Oxazolyl, thiazolyl, pyrazolyl, isoxazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, indolyl, isoindolyl, benzofuranyl, isobenzofuranyl, benzothiophenyl, isobenzo Thiophenyl, indolizinyl, quinolidinyl, quinolyl, isoquinolyl, cinnolyl, phthalazinyl, quinazolinyl, quinoxalinyl, benzimid
  • an arbitrary substituent when “substituted or unsubstituted” is An alkyl group having 1 to 50 carbon atoms (preferably 1 to 10, more preferably 1 to 5); An alkenyl group having 2 to 20 carbon atoms (preferably 2 to 10 carbon atoms); An alkynyl group having 2 to 20 carbon atoms (preferably 2 to 10 carbon atoms); A cycloalkyl group having 3 to 50 ring carbon atoms (preferably 3 to 6, more preferably 5 or 6); An aromatic hydrocarbon group having 6 to 50 ring carbon atoms (preferably 6 to 24, more preferably 6 to 12); Aralkyl having 1 to 50 (preferably 1 to 10, more preferably 1 to 5) carbon atoms having an aromatic hydrocarbon group having 6 to 50 ring carbon atoms (preferably 6 to 24, more preferably 6 to 12) Group; An amino group; A monoalkylamino group or dialkylamino group having an alkyl group having 1 to 50 carbon atoms (preferably 1 to 10, more
  • the number of ring atoms is 5 to 50 (preferably 5 to 24, more preferably 5 to 18), and 1 to 5 (preferably 1 to 3, more preferably) heteroatoms (for example, nitrogen atom, oxygen atom, sulfur atom).
  • substituents in particular, an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group having 5 or 6 carbon atoms, an aromatic hydrocarbon group having 6 to 12 ring carbon atoms, and 5 to 24 ring atom atoms.
  • the alkyl group having 1 to 50 carbon atoms as a substituent in the case of “substituted or unsubstituted” has the same meaning as the group explained as the alkyl group in Ar 1 , Ar 2 and Ar 3 .
  • the alkenyl group having 2 to 20 carbon atoms as a substituent when “substituted or unsubstituted” is synonymous with the group described as the alkenyl group in Ar 1 , Ar 2 and Ar 3 .
  • the alkynyl group having 2 to 20 carbon atoms as a substituent in the case of “substituted or unsubstituted” has the same meaning as the group described as the alkynyl group in Ar 1 , Ar 2 and Ar 3 .
  • the cycloalkyl group having 3 to 50 ring carbon atoms as a substituent in the case of “substituted or unsubstituted” has the same meaning as the group described as the cycloalkyl group in Ar 1 , Ar 2 and Ar 3 .
  • the aromatic hydrocarbon group having 6 to 50 ring carbon atoms as a substituent in the case of “substituted or unsubstituted” has the same meaning as the group described as the aromatic hydrocarbon group in Ar 1 , Ar 2 and Ar 3 . is there.
  • the aralkyl group having 6 to 50 ring carbon atoms as a substituent when “substituted or unsubstituted” has an aromatic hydrocarbon group having 6 to 50 ring carbon atoms and an aralkyl group having 1 to 50 carbon atoms.
  • a specific example of this alkyl group moiety is the same as the above-described alkyl group, and a specific example of the aromatic hydrocarbon group moiety is synonymous with the above-described aromatic hydrocarbon group.
  • specific examples of the alkyl group moiety are the same as the above-described alkyl group.
  • aryloxy group as a substituent when “substituted or unsubstituted” specific examples of the aryl group (aromatic hydrocarbon group) portion are the same as the above-mentioned aromatic hydrocarbon group, and the aryloxy group is For example, a phenoxy group etc. are mentioned.
  • alkylthio group as a substituent in the case of “substituted or unsubstituted”, specific examples of the alkyl group moiety are the same as the above-described alkyl group.
  • Specific examples of the aryl group (aromatic hydrocarbon group) moiety in the arylthio group as a substituent when “substituted or unsubstituted” are the same as the above-described aromatic hydrocarbon group.
  • a mono-substituted silyl group, a di-substituted silyl group or a tri-substituted silyl group as a substituent in the case of “substituted or unsubstituted” includes an alkylsilyl group having 1 to 50 carbon atoms and an arylsilyl having 6 to 50 ring carbon atoms. The group can be mentioned. Examples of the alkylsilyl group having 1 to 50 carbon atoms include a monoalkylsilyl group, a dialkylsilyl group, and a trialkylsilyl group.
  • each alkyl group in the alkylsilyl group having 1 to 50 carbon atoms have the same meaning as the above-described alkyl group.
  • the arylsilyl group having 6 to 50 ring carbon atoms include a monoarylsilyl group, a diarylsilyl group, and a triarylsilyl group.
  • Specific examples of each aryl group in the arylsilyl group having 6 to 50 ring carbon atoms are the same as the above-mentioned aryl group.
  • a trimethylsilyl group for example, a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, Examples thereof include a propyldimethylsilyl group, an isopropyldimethylsilyl group, a triphenylsilyl group, a phenyldimethylsilyl group, a t-butyldiphenylsilyl group, and a tolylsilylsilyl group.
  • the heterocyclic group as a substituent in the case of “substituted or unsubstituted” has the same meaning as the group described as the heterocyclic group in Ar 1 , Ar 2 and Ar 3 .
  • Examples of the haloalkyl group as a substituent in the case of “substituted or unsubstituted” include a group obtained by halogenating the above-described alkyl group, and specific examples include a trifluoromethyl group.
  • R 110 to R 121 are each independently a hydrogen atom or a substituent, and the substituents in these R 110 to R 121 are: Halogen atoms, A cyano group, A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, A substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, A substituted or unsubstituted alkynyl group having 2 to 20 carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms, A substituted or unsubstituted alkylthio group having 1 to 50 carbon atoms, A substituted or unsubstituted aryloxy group having 6 to 50 ring carbon atoms, A substituted or unsubstituted arylthio group having 6 to 50 ring carbon atoms, A substituted or unsub
  • the second material according to this embodiment is a delayed fluorescent material.
  • Delayed fluorescence emission Delayed fluorescence (thermally activated delayed fluorescence) is explained on pages 261 to 268 of “Device characteristics of organic semiconductors” (edited by Chiba Adachi, published by Kodansha). In that document, if the energy difference ⁇ E 13 between the excited singlet state and the excited triplet state of the fluorescent material can be reduced, the reverse energy from the excited triplet state to the excited singlet state, which usually has a low transition probability. Migration occurs with high efficiency and thermally activated delayed fluorescence (thermally activated della). yed Fluorescence (TADF) is expressed. In addition, FIG. 10.38 in this document explains the mechanism of delayed fluorescence generation.
  • the second material in the present embodiment is a compound that exhibits thermally activated delayed fluorescence generated by such a mechanism. The delayed fluorescence emission can be confirmed by transient PL measurement.
  • FIG. 2 shows a schematic diagram of an exemplary apparatus for measuring transient PL.
  • the transient PL measurement apparatus 100 of the present embodiment includes a pulse laser unit 101 that can irradiate light of a predetermined wavelength, a sample chamber 102 that houses a measurement sample, a spectrometer 103 that separates light emitted from the measurement sample, A streak camera 104 for forming a two-dimensional image and a personal computer 105 for capturing and analyzing the two-dimensional image are provided. Note that the measurement of the transient PL is not limited to the apparatus described in this embodiment.
  • the sample accommodated in the sample chamber 102 is obtained by forming a thin film in which a doping material is doped at a concentration of 12 mass% with respect to a matrix material on a quartz substrate.
  • the thin film sample accommodated in the sample chamber 102 is excited by being irradiated with a pulse laser from the pulse laser unit 101.
  • the emitted light is extracted from the direction of 90 degrees of the excitation light, dispersed by the spectroscope 103, and a two-dimensional image is formed in the streak camera 104.
  • a two-dimensional image can be obtained in which the vertical axis corresponds to time, the horizontal axis corresponds to wavelength, and the bright spot corresponds to emission intensity.
  • a thin film sample A was prepared as described above using the following reference compound H1 as a matrix material and the following reference compound D1 as a doping material, and transient PL measurement was performed.
  • Transient PL is a technique for measuring the decay behavior (transient characteristics) of PL emission after irradiating a sample with a pulsed laser and exciting it and stopping the irradiation.
  • PL emission in the TADF material is classified into a light emission component from a singlet exciton generated by the first PL excitation and a light emission component from a singlet exciton generated via a triplet exciton.
  • the lifetime of singlet excitons generated by the first PL excitation is on the order of nanoseconds and is very short. Therefore, light emitted from the singlet excitons is rapidly attenuated after irradiation with the pulse laser.
  • delayed fluorescence is emitted slowly from singlet excitons generated via a long-lived triplet exciton, and thus slowly attenuates.
  • the emission intensity derived from delayed fluorescence can be obtained.
  • FIG. 3 shows attenuation curves obtained from the transient PL measured for the thin film sample A and the thin film sample B.
  • the transient PL measurement it is possible to obtain a light emission decay curve with the vertical axis representing the emission intensity and the horizontal axis representing the time. Based on this emission decay curve, the fluorescence intensity of fluorescence emitted from the singlet excited state generated by photoexcitation and delayed fluorescence emitted from the singlet excited state generated by reverse energy transfer via the triplet excited state The ratio can be estimated. In the delayed fluorescence emitting material, the ratio of the delayed fluorescence intensity that attenuates slowly is somewhat larger than the fluorescence intensity that decays quickly.
  • the delayed fluorescence emission amount in this embodiment can be obtained using the apparatus shown in FIG.
  • Light emission from the second material includes Prompt light emission (immediate light emission) and Delay light emission (delayed light emission).
  • Prompt light emission is light emission that is immediately observed from the excited state after being excited by pulsed light having a wavelength that is absorbed by the second material (light irradiated from a pulse laser).
  • Delay light emission is light emission that is not observed immediately after excitation by the pulsed light but is observed thereafter.
  • the amount of delay light emission (delayed light emission) is preferably 5% or more with respect to the amount of Promp light emission (immediate light emission).
  • the amounts of Prompt light emission and Delay light emission can be obtained by a method similar to the method described in “Nature 492, 234-238, 2012” (reference document 1).
  • the apparatus used for calculation of the amount of Promp light emission and Delay light emission is not limited to the apparatus described in Reference Document 1.
  • a sample prepared by the following method is used for the measurement of delayed fluorescence.
  • a second material and a compound TH-2 which will be described later, are co-evaporated on a quartz substrate so that the ratio of the second material is 12% by mass, and a thin film having a thickness of 100 nm is formed to prepare a sample. To do.
  • the second material preferably has a partial structure represented by the following general formula (2) and a partial structure represented by the following general formula (2Y) in one molecule.
  • CN is a cyano group.
  • n is an integer of 1 or more.
  • n is preferably an integer of 1 or more and 5 or less, and more preferably an integer of 2 or more and 4 or less.
  • Z 1 to Z 6 are each independently a nitrogen atom, a carbon atom bonded to CN, or a carbon atom bonded to another atom in the molecule of the second material.
  • Z 1 is a carbon atom bonded to CN
  • at least one of the remaining five (Z 2 to Z 6 ) is a carbon atom bonded to another atom in the molecule of the second material; Become.
  • the other atom may be an atom constituting a partial structure represented by the following general formula (2Y), or may be an atom constituting a linking group or a substituent intervening with the partial structure.
  • the second material according to the present embodiment may have a 6-membered ring composed of Z 1 to Z 6 as a partial structure, or a condensed structure formed by further condensing the 6-membered ring with a ring. You may have a ring as a partial structure.
  • F and G each independently represent a ring structure.
  • m is 0 or 1.
  • Y 20 represents a single bond, an oxygen atom, a sulfur atom, a selenium atom, a carbon atom, a silicon atom, or a germanium atom.
  • the ring structure F and the ring structure G in the general formula (20Y) have the same meaning as the ring structure F and the ring structure G in the general formula (2Y).
  • the ring structure F and the ring structure G have the same meanings as the ring structure F and the ring structure G in the general formula (2Y).
  • the ring structure F and the ring structure G are preferably a 5-membered ring or a 6-membered ring, and the 5-membered ring or 6-membered ring is preferably an unsaturated ring, More preferably, it is a member ring.
  • the second material according to this embodiment is preferably a compound represented by the following general formula (20).
  • A is represented by the general formula (2), provided that in the general formula (2), CN is a cyano group, n is an integer of 1 or more, and Z 1 to Z 6 are each independently And a nitrogen atom, a carbon atom bonded to CN, a carbon atom bonded to R, a carbon atom bonded to L, or a carbon atom bonded to D, and a carbon atom bonded to CN among Z 1 to Z 6 And at least one carbon atom bonded to L or D, Each R is independently a hydrogen atom or a substituent.
  • the substituent in R is a halogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted ring formation.
  • Aromatic heterocyclic group having 5 to 30 atoms, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, substituted or unsubstituted ring forming carbon number 6 to 60 arylsilyl groups, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 ring carbon atoms, substituted or unsubstituted 2 to 30 carbon atoms Alkylamino group, substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms, substituted or unsubstituted alkylthio
  • D is represented by the general formula (2Y), provided that the ring structure F and the ring structure G in the general formula (2Y) may be unsubstituted or have a substituent.
  • m is 0 or 1
  • Y 20 is a single bond, oxygen atom, sulfur atom, selenium atom, carbonyl group, CR 21 R 22 , SiR 23 R 24 or GeR 25. It represents R 26, R 21 ⁇ R 26 has the same meaning as the groups mentioned in the R.
  • the general formula (2Y) when m is 1, the general formula (2Y) is represented by any one of the general formulas (22) to (25) and the following general formulas (21Y) to (24Y). Is done.
  • f is an integer of 1 or more
  • e and g are each independently an integer of 0 or more.
  • A may mutually be same or different.
  • D may mutually be same or different.
  • L may mutually be same or different.
  • the general formula (20) is represented by the following general formulas (201) to (220), for example.
  • D in the repeating unit enclosed in parentheses having the repeating number f, D may be bonded to A via L, or via L to D.
  • A may be bonded.
  • they may be branched as in the following general formulas (221) to (228).
  • the second material according to the present embodiment is not limited to the compounds represented by the general formulas (201) to (228).
  • L when L is omitted, L is a single bond interposed between A and D, or L is in the molecule of the second material. Indicates a hydrogen atom located at the end.
  • L is not a condensed aromatic ring in terms of molecular design, but a condensed aromatic ring is also employed as long as thermally active delayed fluorescence can be obtained. Can do.
  • the 2nd material which concerns on this embodiment is a low molecular material. Therefore, the second material according to this embodiment preferably has a molecular weight of 5000 or less, and more preferably has a molecular weight of 3000 or less. It is preferable that the 2nd material which concerns on this embodiment contains the partial structure of the said General formula (2) and the said General formula (2Y).
  • the organic EL element containing the second material emits light using a thermally activated delayed fluorescence mechanism.
  • the general formula (2Y) is preferably represented by at least one of the following general formula (2a) and the following general formula (2x).
  • a and B each independently represent a ring structure represented by the following general formula (2c) or a ring structure represented by the following general formula (2d),
  • the ring structure B is condensed with an adjacent ring structure at an arbitrary position.
  • px and py are each independently an integer of 0 or more and 4 or less, and represent the numbers of the ring structure A and the ring structure B, respectively.
  • the plurality of ring structures A may be the same as or different from each other.
  • py is an integer of 2 or more and 4 or less
  • the plurality of ring structures B may be the same as or different from each other.
  • the ring structure A may have two ring structures represented by the following general formula (2c) or two ring structures represented by the following general formula (2d).
  • the ring structure A may have two ring structures represented by the following general formula (2c) or two ring structures represented by the following general formula (2d).
  • a combination of one ring structure represented by the following general formula (2c) and one ring structure represented by the following general formula (2d) may be used.
  • c is an integer of 1 to 4.
  • the plurality of ring structures E may be the same as or different from each other.
  • E represents a ring structure represented by the general formula (2c) or a ring structure represented by the general formula (2d)
  • the ring structure E represents an adjacent ring structure and Condensation at any position. Therefore, for example, when c is 2, the two ring structures E may have two ring structures represented by the general formula (2c) or two ring structures represented by the general formula (2d).
  • One ring structure represented by the general formula (2c) may be combined with one ring structure represented by the general formula (2d).
  • the second material according to the present embodiment preferably has a structure represented by the following general formula (2e) in the molecule.
  • R 1 to R 9 are each independently a hydrogen atom, a substituent, or a single bond that binds to another atom in the molecule of the second material;
  • the substituents in R 1 to R 9 are halogen atoms, substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms, substituted or unsubstituted aromatic heterocyclic groups having 5 to 30 ring atoms, substituted Or an unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted group;
  • R 1 to R 9 is a single bond that bonds to another atom in the molecule of the second material.
  • at least one of the combinations of substituents selected from R 1 to R 9 may be bonded to each other to form a ring structure.
  • this ring structure that is, in the general formula (2e), among the 6-membered ring carbon atoms or 5-membered ring nitrogen atoms to which R 1 to R 9 are respectively bonded, Substituents selected from R 1 to R 8 and R 9 bonded to a 5-membered ring nitrogen atom can form a ring structure.
  • the ring structure formed by combining substituents with each other is preferably a condensed ring.
  • a case where a condensed 6-membered ring structure is formed can be considered.
  • the second material according to the present embodiment preferably has a structure represented by the following general formula (2y) in the molecule.
  • R 11 to R 19 in the general formula (2y) are independently the same as R 1 to R 9 in the general formula (2e). However, at least one of R 11 to R 19 is a single bond that bonds to another atom in the molecule of the second material. In the general formula (2y), at least one of the combinations of substituents selected from R 11 to R 19 may be bonded to each other to form a ring structure.
  • a and B each independently represent a ring structure represented by the following general formula (2g) or a ring structure represented by the following general formula (2h), The ring structure B is condensed with an adjacent ring structure at an arbitrary position.
  • px is the number of the ring structure A, and is an integer of 0 or more and 4 or less.
  • the plurality of ring structures A may be the same as or different from each other.
  • the plurality of ring structures A may be the same as or different from each other.
  • py is the number of ring structures B and is an integer of 0 or more and 4 or less. Therefore, for example, when px is 2, the two ring structures A may have two ring structures represented by the following general formula (2g), or two ring structures represented by the following general formula (2h). Or a combination of one ring structure represented by the following general formula (2g) and one ring structure represented by the following general formula (2h).
  • R 201 and R 202 are each independently synonymous with R 1 to R 9 , and R 201 and R 202 may be bonded to each other to form a ring structure. .
  • R 201 and R 202 are each bonded to a carbon atom forming the 6-membered ring of the general formula (2g).
  • Z 8 represents CR 203 R 204 , NR 205 , a sulfur atom, or an oxygen atom, and R 202 to R 205 are each independently a substituent in R 1 to R 9 It is synonymous.
  • at least one of the combinations of substituents selected from R 11 to R 19 and R 201 to R 205 may be bonded to each other to form a ring structure.
  • R 11 to R 19 in the general formula (2f) are independently the same as R 1 to R 9 in the general formula (2e). However, at least one of R 11 to R 19 is a single bond that bonds to another atom in the molecule of the second material. In the general formula (2f), at least one of the combinations of substituents selected from R 11 to R 19 may be bonded to each other to form a ring structure.
  • E represents a ring structure represented by the general formula (2g) or a ring structure represented by the general formula (2h), and the ring structure E represents an adjacent ring structure. And condensed at any position.
  • c is the number of the ring structure E, and is an integer of 1 or more and 4 or less.
  • the plurality of ring structures E may be the same as or different from each other. Therefore, for example, when c is 2, the two ring structures E may have two ring structures represented by the general formula (2g) or two ring structures represented by the general formula (2h). Or a combination of one ring structure represented by the following general formula (2g) and one ring structure represented by the general formula (2h).
  • the second material according to the present embodiment is preferably represented by the following general formula (2A).
  • n is an integer of 1 or more
  • t is an integer of 1 or more
  • u is an integer of 0 or more.
  • L A is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 ring carbon atoms or an aromatic heterocyclic ring having 6 to 30 ring atoms.
  • CN is a cyano group.
  • D 1 and D 2 are each independently represented by the general formula (2Y), provided that the ring structure F and the ring structure G in the general formula (2Y) may be unsubstituted or have a substituent.
  • m is 0 or 1
  • Y 20 is a single bond, oxygen atom, sulfur atom, selenium atom, carbonyl group, CR 21 R 22 , SiR 23 R 24 or GeR 25.
  • R 26 R 21 ⁇ R 26 are the same as defined above R.
  • the general formula (2Y) is represented by any one of the general formulas (22) to (25) and the general formulas (21Y) to (24Y).
  • D 1 and D 2 may be the same or different.
  • t is 2 or more
  • the plurality of D 1 may be the same as or different from each other.
  • u is 2 or more
  • the plurality of D 2 may be the same as or different from each other.
  • L A is preferably a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 14 ring carbon atoms.
  • the aromatic hydrocarbon ring having 6 to 14 ring carbon atoms include benzene, naphthalene, fluorene, and phenanthrene.
  • L A is more preferably an aromatic hydrocarbon ring having 6 to 10 ring carbon atoms.
  • the aromatic heterocyclic ring atoms 6 to 30 in the L A for example, pyridine, pyrimidine, pyrazine, quinoline, quinazoline, phenanthroline, benzofuran, and dibenzofuran, and the like.
  • the first of the D 1 or the D 2 is bonded to the carbon atoms forming the aromatic hydrocarbon ring represented by L A, the first The CN may be bonded to the second carbon atom adjacent to the carbon atom.
  • the second material according to this embodiment as in the partial structure represented by the following general formula (2B), wherein D is attached to the first carbon atom C 1, the first carbon atom C A cyano group may be bonded to the second carbon atom C 2 adjacent to 1 .
  • D in the following general formula (2B) has the same meaning as D 1 or D 2 .
  • a wavy line portion represents a bonding position with another structure or atom.
  • D 1 or D 2 having the structure as shown in formula (2a) or Formula (2b), bonded to the aromatic hydrocarbon ring is a cyano group represented by adjacent said L A
  • the value of ⁇ ST of the compound can be reduced.
  • the t is preferably an integer of 2 or more. If the said D 1 of the 2 or more aromatic hydrocarbon ring represented by L A is attached, a plurality of D 1 may be a different structure may be the same structure.
  • the second material according to the present embodiment is preferably represented by the following general formula (21).
  • a 21 and B 21 each independently represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring atom having 5 to 5 ring atoms.
  • 30 aromatic heterocyclic groups are represented.
  • X 21 to X 28 and Y 21 to Y 28 each independently represent a nitrogen atom, a carbon atom bonded to R D , or a carbon atom bonded to L 23 .
  • at least one of X 25 to X 28 is a carbon atom bonded to L 23, and at least one of Y 21 to Y 24 is a carbon atom bonded to L 23 .
  • Each RD is independently a hydrogen atom or a substituent.
  • the substituent in RD is a halogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted group. It is a substituent selected from the group consisting of a substituted aromatic heterocyclic group having 5 to 30 ring atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and a substituted or unsubstituted silyl group.
  • L 21 and L 22 are each independently a single bond or a linking group, and examples of the linking group in L 21 and L 22 include a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted group.
  • L 23 represents a substituted or unsubstituted monocyclic hydrocarbon group having 6 or less ring-forming carbon atoms, or a substituted or unsubstituted monocyclic heterocyclic group having 6 or less ring-forming atoms.
  • w represents an integer of 0 to 3. When w is 0, at least one of X 25 to X 28 and at least one of Y 21 to Y 24 are directly bonded.
  • a monocyclic hydrocarbon group is not a condensed ring but a group derived from a single hydrocarbon ring (aliphatic cyclic hydrocarbon or aromatic hydrocarbon), and a monocyclic heterocyclic group is a single ring A group derived from a heterocyclic ring.
  • At least one of the following conditions (i) and (ii) is satisfied.
  • At least one of A 21 and B 21 is an aromatic hydrocarbon group having 6 to 30 ring carbon atoms substituted with a cyano group, or an aromatic group having 6 to 30 ring atoms substituted with a cyano group Group heterocyclic group.
  • At least one of (ii) X 21 ⁇ X 24 and Y 25 ⁇ Y 28 is a carbon atom bonded with R D, the R at least one of D is, ring carbon 6 is substituted with a cyano group
  • R D there are a plurality, or different in each of the plurality of R D identical.
  • the aromatic hydrocarbon group having 6 to 30 ring carbon atoms or the aromatic heterocyclic group having 6 to 30 ring atoms represented by A 21 and B 21 has a substituent.
  • the substituent is a cyano group, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, Haloalkoxy group having 1 to 20 carbon atoms, alkylsilyl group having 1 to 10 carbon atoms, aryl group having 6 to 30 ring carbon atoms, aryloxy group having 6 to 30 ring carbon atoms, aralkyl having 6 to 30 carbon atoms
  • the group is preferably one or more groups selected from the group consisting of a group and a heterocyclic group having 5 to 30 ring atoms.
  • condition (i) it is preferable that the condition (i) is satisfied and the condition (ii) is not satisfied. Alternatively, in the general formula (21), it is preferable that the condition (ii) is satisfied and the condition (i) is not satisfied. Alternatively, it is also preferable to satisfy the condition (i) and the condition (ii).
  • At least one of A 21 and B 21 is A phenyl group substituted with a cyano group, A naphthyl group substituted with a cyano group, A phenanthryl group substituted with a cyano group, A dibenzofuranyl group substituted with a cyano group, A dibenzothiophenyl group substituted with a cyano group, A biphenyl group substituted with a cyano group, A terphenyl group substituted with a cyano group, A 9,9-diphenylfluorenyl group substituted with a cyano group, A 9,9′-spirobi [9H-fluoren] -2-yl group substituted with a cyano group, A 9,9-dimethylfluorenyl group substituted with a cyano group or a triphenylenyl group substituted with a cyano group is preferred.
  • At least one of X 21 ⁇ X 24 and Y 25 ⁇ Y 28 is CR D, at least one of R D in X 21 ⁇ X 24 and Y 25 ⁇ Y 28 is, A phenyl group substituted with a cyano group, A naphthyl group substituted with a cyano group, A phenanthryl group substituted with a cyano group, A dibenzofuranyl group substituted with a cyano group, A dibenzothiophenyl group substituted with a cyano group, A biphenyl group substituted with a cyano group, A terphenyl group substituted with a cyano group, A 9,9-diphenylfluorenyl group substituted with a cyano group, A 9,9′-spirobi [9H-fluoren] -2-yl group substituted with a cyano group, A 9,9-dimethylfluorenyl group substituted with a
  • X 26 and Y 23 are preferably bonded via L 23 or directly bonded. Further, in the general formula (21), and X 26 and Y 22 is either attached via a L 23, or is preferably bonded directly. Further, in the general formula (21), and X 27 and Y 23 is either attached via a L 23, or is preferably bonded directly.
  • w is preferably 0.
  • w is preferably 1.
  • L 21 and L 22 are preferably a single bond or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.
  • the second material is a carbon atom having a partial structure represented by the general formula (2), for example, and at least one of Z 1 to Z 6 is bonded to a halogen atom.
  • a compound in which a commercially available compound is represented by the general formula (2Y) in the presence of a catalyst such as tetrakis (triphenylphosphine) palladium and a base, and a hydrogen atom is bonded to a nitrogen atom bonded to the ring structure F and the ring structure G Can be made to react.
  • the singlet energy of the 3rd material which concerns on this embodiment is larger than the singlet energy of said 2nd material.
  • the third material may include at least one of a partial structure represented by the following general formula (31) and a partial structure represented by the following general formula (32) in one molecule. preferable.
  • X 31 ⁇ X 36 are each independently a carbon atom bonded with other atoms on the nitrogen atom or the molecule of the third material, with the proviso, X 31 ⁇ X At least one of 36 is a carbon atom bonded to another atom in the molecule of the third material;
  • Y 31 to Y 38 are each independently a nitrogen atom or a carbon atom bonded to another atom in the molecule of the third material, provided that Y 31 to Y 38 At least one of them is a carbon atom bonded to another atom in the molecule of the third material, and Y 39 is a nitrogen atom, an oxygen atom, or a sulfur atom.
  • the partial structure represented by the general formula (31) is the third material as at least one group selected from the group consisting of the following general formula (33) and the following general formula (34). It is preferable that it is contained in. As represented by the following general formula (33) and the following general formula (34), it is possible to keep the energy gap Eg 77K (M3) at 77 [K] high because the bonding sites are located at the meta positions. Therefore, it is preferable as the third material.
  • X 31 , X 32 , X 34 , and X 36 are each independently a nitrogen atom or CR 31 , and R 31 is a hydrogen atom or a substituent.
  • R 31 is a hydrogen atom or a substituent.
  • the substituent in R 31 is Halogen atoms, A cyano group, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, A substituted or unsubstituted trialkylsilyl group, A substituted or unsubstituted arylalkylsilyl group, A substituted or unsubstituted triarylsilyl group, Substituted or unsubstituted diarylphosphine oxide groups, A substituent selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted
  • 31 is more preferably a hydrogen atom, a cyano group, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. preferable.
  • X 31 , X 32 , X 34 , and X 36 are each independently CR 31 .
  • X 32 , X 34 , and X 36 are each independently CR 31 .
  • the partial structure represented by the general formula (32) includes the following general formula (35), the following general formula (36), the following general formula (37), the following general formula (38), and the following general formula. (39) and at least one group selected from the group consisting of the following general formula (30a) is preferably included in the third material. Bonding sites as represented by the following general formula (35), the following general formula (36), the following general formula (37), the following general formula (38), the following general formula (39), and the following general formula (30a) Is preferable as the third material because the energy gap Eg 77K at 77 [K] can be kept high.
  • Y 31 to Y 38 are each independently a nitrogen atom or CR 32 ;
  • R 32 is a hydrogen atom or a substituent, and the substituent in R 32 is Halogen atoms, A cyano group, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, A substituted or unsubstituted trialkylsilyl group, A substituted or unsubstituted arylalkylsilyl group, A substituted or unsubstituted triarylsilyl group, Substituted or unsubstituted diarylphosphine oxide groups, A substituent selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ;
  • R 32 is a hydrogen atom or a substituent, and the substituent in R 32 is a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted group. It is preferably a substituent selected from the group consisting of a substituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. 32 is more preferably a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
  • Y 31 to Y 38 are preferably each independently CR 32 .
  • Y 31 to Y 35 , Y 37 , and Y 38 are preferably each independently CR 32 .
  • Y 31 , Y 32 , Y 34 , Y 35 , Y 37 , Y 38 are preferably each independently CR 32 .
  • Y 32 to Y 38 are preferably each independently CR 32 .
  • Y 32 to Y 37 are preferably each independently CR 32 .
  • the plurality of R 32 may be the same or different.
  • the third material preferably includes a group represented by the following general formula (30b). It is preferable for the third material to be located as represented by the following general formula (30b) because the energy gap Eg 77K at 77 [K] can be kept high.
  • X 31 , X 32 , X 34 , and X 36 are each independently a nitrogen atom or CR 31 , Y 31 , Y 32 , Y 34 to Y 38 are each independently a nitrogen atom, CR 32 , or a carbon atom that is bonded to another atom in the molecule of the third material;
  • R 31 and R 32 are each independently a hydrogen atom or a substituent, and the substituent in R 31 and R 32 is a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, Substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted trialkylsilyl group, substituted or unsubstituted arylalkylsilyl group, substituted or unsubstituted triarylsilyl group, substituted or unsubstituted
  • R 31 and the R substituted or unsubstituted in the 32 ring carbon atoms 6 to 30 Hydrocarbon group is a non-fused ring
  • Y 39 is NR 33 , an oxygen atom, or a sulfur atom
  • R 33 is a substituent
  • the substituent in R 33 is a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms.
  • Z 31 is an oxygen atom, a sulfur atom, or CR 51 R 52 .
  • the third material preferably includes a group represented by the following general formula (30c). Positioning the bonding site as represented by the following general formula (30c) is preferable as the third material because the energy gap Eg 77K at 77 [K] can be kept high.
  • X 31 , X 32 , X 34 , and X 36 are each independently a nitrogen atom or CR 31 , Y 31 , Y 32 , Y 34 , Y 35 , Y 37 , Y 38 are each independently a nitrogen atom or CR 32 , Y 41 to Y 45 , Y 47 , and Y 48 are each independently a nitrogen atom, CR 34 , or a carbon atom bonded to another atom in the molecule of the third material;
  • R 31 , R 32 , and R 34 are each independently a hydrogen atom or a substituent, and the substituent in R 31 , R 32 , and R 34 is a halogen atom, a cyano group, a substituted or unsubstituted carbon number of 1 -30 alkyl groups, substituted or unsubstituted cycloalkyl groups having 3 to 30 ring carbon atoms, substituted or unsubstituted trialkyls
  • the substituent in R 33 and R 35 is a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted ring.
  • Z 32 is an oxygen atom, a sulfur atom, or CR 51 R 52 .
  • the third material includes a group represented by the following general formula (30d). Positioning the bonding site as represented by the following general formula (30d) is preferable as the third material because the energy gap Eg 77K at 77 [K] can be kept high.
  • X 31 , X 32 , X 34 , and X 36 are each independently a nitrogen atom or CR 31
  • X 41 , X 43 , X 44 , and X 45 are each independently a nitrogen atom or CR 36
  • R 31 and R 36 are each independently a substituent.
  • the substituent in R 31 and R 36 is a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted group.
  • Substituted cycloalkyl group having 3 to 30 carbon atoms substituted or unsubstituted trialkylsilyl group, substituted or unsubstituted arylalkylsilyl group, substituted or unsubstituted triarylsilyl group, substituted or unsubstituted diaryl
  • R 31, the aromatic hydrocarbon group substituted or unsubstituted ring carbon number of 6 to 30 in R 36 is unfused rings Yes
  • X 32 and X 41 may be cross-linked via an oxygen atom, a sulfur atom, or CR 55 R 56
  • X 34 and X 45 may be cross-linked via an oxygen atom, a sulfur atom, or CR 57 R 58
  • R 55 to R 58 are each independently a substituent.
  • the substituent in R 55 to R 58 is a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted group.
  • Z 33 represents an oxygen atom, a sulfur atom, or CR 55 R 56 .
  • the third material preferably includes a group represented by the following general formula (30e). It is preferable for the third material to be located as represented by the following general formula (30e) because the energy gap Eg 77K at 77 [K] can be kept high.
  • X 31 , X 32 , X 34 , and X 36 are each independently a nitrogen atom or CR 31 , X 41 , X 43 , X 44 , and X 45 are each independently a nitrogen atom or CR 36 , Y 31 to Y 35 , Y 37 , and Y 38 are each independently a nitrogen atom, CR 32 , or a carbon atom bonded to another atom in the molecule of the third material; R 31 , R 32 , and R 36 are each independently a hydrogen atom or a substituent, and the substituent in R 31 and R 36 is a halogen atom, a cyano group, a substituted or unsubstituted C 1-30 carbon atom.
  • Z 34 represents an oxygen atom, a sulfur atom, or CR 55 R 56 .
  • Z 35 represents an oxygen atom, a sulfur atom, or CR 59 R 60 .
  • the third material preferably includes a group represented by the following general formula (30f). Positioning the bonding site as represented by the following general formula (30f) is preferable as the third material because the energy gap Eg 77K at 77 [K] can be kept high.
  • R 32 the above substituted or unsubstituted ring carbon atoms 6 to 30 in R 34 the aromatic hydrocarbon It is a non-fused ring
  • Y 39 is NR 33 , an oxygen atom, or a sulfur atom
  • Y 49 is NR 35 , an oxygen atom, or a sulfur atom
  • R 33 and R 35 are each independently a hydrogen atom or a substituent.
  • the substituent in R 33 and R 35 is a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted group.
  • the third material may include a group represented by at least one of the following general formula (30g), the following general formula (30h), and the following general formula (30i).
  • the substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms in R 37 is a non-condensed ring
  • Y 49 and Y 59 are each independently NR 38 , an oxygen atom, or a sulfur atom
  • R 38 is each independently a hydrogen atom or a substituent
  • the substituent in R 38 is a halogen atom
  • the aromatic hydrocarbon group having 6 to 30 carbon atoms is a non-condensed ring
  • a wavy line portion represents a bonding site with another atom or another structure in the molecule of the third material.
  • Y 39 and Y 49 are When each is independently an oxygen atom or a sulfur atom, the ionization potential Ip is large, so that it is preferable as the third material, and when it is an oxygen atom, the ionization potential Ip is larger, more preferable.
  • the third material is preferably an aromatic hydrocarbon compound or an aromatic heterocyclic compound.
  • the third material of the general formula is obtained by, for example, a method described in International Publication No. 2012/153780 (WO2012 / 153780A1) or International Publication No. 2013/038650 (WO2013-038650A1). Can be manufactured.
  • aromatic hydrocarbon group examples include phenyl group, tolyl group, xylyl group, naphthyl group, phenanthryl group, pyrenyl group, chrysenyl group, benzo [c] phenanthryl group, benzo [g] chrysenyl group Group, benzoanthryl group, triphenylenyl group, fluorenyl group, 9,9-dimethylfluorenyl group, benzofluorenyl group, dibenzofluorenyl group, biphenyl group, terphenyl group, quarterphenyl group, fluoranthenyl group
  • a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, a naphthyl group, a triphenylenyl group, a fluorenyl group and the like can be mentioned.
  • aromatic hydrocarbon group having a substituent examples include a tolyl group, a xylyl group, and a 9,9-dimethylfluorenyl group.
  • aryl groups include both fused and non-fused aryl groups.
  • the aromatic hydrocarbon group a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, a naphthyl group, a triphenylenyl group, and a fluorenyl group are preferable.
  • the aromatic hydrocarbon group as a substituent in the third material is preferably a non-condensed aromatic hydrocarbon group.
  • aromatic heterocyclic group examples include pyrrolyl group, pyrazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, pyridyl group, triazinyl group, indolyl group, Isoindolyl group, imidazolyl group, benzimidazolyl group, indazolyl group, imidazo [1,2-a] pyridinyl group, furyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, azadibenzofuranyl group, thiophenyl group, Benzothiophenyl group, dibenzothiophenyl group, azadibenzothiophenyl group, quinolyl group, isoquinolyl group, quinoxalinyl group, quinazolinyl group, naphth
  • Examples thereof include a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a pyridyl group, a pyrimidinyl group, a triazinyl group, an azadibenzofuranyl group, and an azadibenzothiophenyl group.
  • dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, pyridyl group, pyrimidinyl group, triazinyl group, azadibenzofuranyl group, azadibenzothiophenyl group are preferable, dibenzofuranyl group, dibenzofuranyl group A thiophenyl group, an azadibenzofuranyl group, and an azadibenzothiophenyl group are more preferable.
  • trialkylsilyl group examples include a trimethylsilyl group and a triethylsilyl group.
  • substituted or unsubstituted arylalkylsilyl group examples include a diphenylmethylsilyl group, a ditolylmethylsilyl group, and a phenyldimethylsilyl group.
  • substituted or unsubstituted triarylsilyl group examples include a triphenylsilyl group and a tolylsilylsilyl group.
  • diarylphosphine oxide group examples include a diphenylphosphine oxide group and a ditolylphosphine oxide group.
  • R 1 , R a , Ar 1 , Ar 2 , Ar 3 , Ar 4 has a substituent
  • these substituents are substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted A cycloalkyl group having 3 to 30 ring carbon atoms, a substituted or unsubstituted trialkylsilyl group, a substituted or unsubstituted arylalkylsilyl group, a substituted or unsubstituted triarylsilyl group, a substituted or unsubstituted diarylphosphine
  • the hydrogenated ring group include phenyl group, tolyl group, xylyl group, naphthyl group, phenanthryl group, pyrenyl group, chrysenyl group, benzo [c] phenanthryl group, benzo [g] chrysenyl group, benzoanthryl group, Triphenylenyl group, fluorenyl group, 9,9-dimethylfluorenyl group, benzofluorenyl group, dibenzofluorenyl group, biphenyl group, terphenyl group, quarterphenyl group, fluoranthenyl group, etc.
  • aromatic Specific examples of the heterocyclic group include pyrrolyl, pyrazolyl, pyrazinyl, pyrimidinyl
  • the third material is considered to have a function as a dispersion material that suppresses molecular association of the second materials according to the above-described embodiment in the light emitting layer. Since the second material according to the present embodiment is a thermally activated delayed fluorescent material, it tends to cause molecular association.
  • the excitation energy (singlet energy or triplet energy) of the molecular aggregate is small compared to the excitation energy of the monomer. Therefore, when the concentration of the second material is increased in the thin film, energy loss due to molecular association is predicted.
  • the use of the third material suppresses the energy loss due to the above-described molecular association and improves the efficiency of the organic EL element. Even when a light emitting material that emits light in the wavelength range from the red light emitting wavelength region to the yellow light emitting wavelength region is used for the light emitting layer, the carrier balance factor is improved by using the third material. The efficiency of the organic EL element is improved.
  • the thermally activated delayed fluorescence organic EL element of the present embodiment the thermally activated delayed fluorescent material having a relatively small singlet energy is responsible for carrier transport in the light emitting layer, and the singlet energy is higher than that of the second material. Since the third material having a large size is relatively difficult to carry carrier transport, there is a possibility of greatly changing the carrier balance factor.
  • the singlet energy EgS (M2) of the second material is preferably larger than the singlet energy EgS (M1) of the first material. That is, it is preferable to satisfy the relationship of EgS (M1) ⁇ EgS (M2) ⁇ EgS (M3).
  • the energy gap Eg 77K (M2) at 77 [K] of the second material is larger than the energy gap Eg 77K (M1) at 77 [K] of the first material, and the third material
  • the energy gap Eg 77K (M3) at 77 [K] of the material is preferably larger than the energy gap Eg 77K (M2) at 77 [K] of the second material. That is, it is preferable to satisfy the relationship of Eg 77K (M1) ⁇ Eg 77K (M2) ⁇ Eg 77K (M3).
  • the difference ⁇ ST (M2) between the singlet energy EgS (M2) of the second material and the energy gap Eg 77K (M2) at 77 [K] of the second material is expressed by the following formula ( It is preferable to satisfy the relationship of equation (1).
  • ⁇ ST (M2) EgS (M2) ⁇ Eg 77K (M2) ⁇ 0.3 [eV] (Equation 1)
  • ⁇ ST (M2) is preferably less than 0.2 [eV].
  • the difference ⁇ ST (M1) between the singlet energy EgS (M1) of the first material and the energy gap Eg 77K (M1) at 77 [K] of the first material is expressed by the following formula ( It is preferable to satisfy the relationship of Formula 2).
  • ⁇ ST (M1) EgS (M1) ⁇ Eg 77K (M1)> 0.3 [eV] (Equation 2)
  • the difference ⁇ ST (M3) between the singlet energy EgS (M3) of the third material and the energy gap Eg 77K (M3) at 77 [K] of the third material is expressed by the following formula ( It is preferable to satisfy the relationship of Equation 3).
  • ⁇ ST (M3) EgS (M3) ⁇ Eg 77K (M3)> 0.3 [eV] (Equation 3)
  • the energy gap Eg 77K (M3) at 77 [K] of the third material is preferably 2.9 eV or more.
  • the third material can be hardly involved in exciton generation or carrier transport in the light emitting layer.
  • a compound having a small ⁇ ST used for the second material of the present embodiment is a compound in which a donor element and an acceptor element are combined in the molecule, and further, electrochemical stability (redox stability) is considered. And compounds having ⁇ ST of 0 eV or more and less than 0.3 eV. Further, a more preferable compound is a compound that forms an aggregate in which dipoles formed in an excited state of a molecule interact with each other and exchange interaction energy becomes small. According to the study by the present inventors, such a compound has approximately the same dipole direction, and ⁇ ST can be further reduced by molecular interaction. In such a case, ⁇ ST can be extremely small, from 0 eV to 0.2 eV.
  • FIG. 4 shows an example of the relationship between the energy levels of the first material, the second material, and the third material in the light emitting layer.
  • S0 represents the ground state
  • S1 (M1) represents the lowest excited singlet state of the first material
  • T1 (M1) represents the lowest excited triplet state of the first material
  • S1 (M2) represents the lowest excited singlet state of the second material
  • T1 (M2) represents the lowest excited triplet state of the second material
  • S1 (M3) represents the lowest material of the third material. It represents an excited singlet state
  • T1 (M3) represents the lowest excited triplet state of the third material.
  • the dashed arrow from S1 (M2) to S1 (M1) in FIG. 4 represents the Forster energy transfer from the lowest excited singlet state of the second material to the lowest excited singlet state of the first material. . As shown in FIG.
  • the energy gap at 77 [K] is different from the normally defined triplet energy.
  • a phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) is measured at a low temperature (77 [K]), and a tangent line is drawn with respect to the rising edge of the phosphorescence spectrum on the short wavelength side.
  • the energy amount calculated from the following conversion formula 1 was defined as an energy gap Eg 77K at 77 [K].
  • an F-4500 spectrofluorometer main body manufactured by Hitachi High-Technology Co., Ltd. was used.
  • the tangent to the rising edge on the short wavelength side of the phosphorescence spectrum is drawn as follows. When moving on the spectrum curve from the short wavelength side of the phosphorescence spectrum to the maximum value on the shortest wavelength side among the maximum values of the spectrum, tangents at each point on the curve are considered toward the long wavelength side. The slope of this tangent line increases as the curve rises (that is, as the vertical axis increases). A tangent drawn at a point where the value of the slope takes a maximum value (that is, a tangent at the inflection point) is a tangent to the rising edge of the phosphorescence spectrum on the short wavelength side.
  • the maximum point having a peak intensity of 15% or less of the maximum peak intensity of the spectrum is not included in the above-mentioned maximum value on the shortest wavelength side, and has the maximum slope value closest to the maximum value on the shortest wavelength side.
  • the tangent drawn at the point where the value is taken is taken as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side.
  • the triplet energy is measured as follows. A sample (second material) to be measured and the compound TH-2 are co-evaporated on a quartz substrate, and a sample sealed in an NMR tube is prepared. This sample was produced under the following conditions.
  • Quartz substrate / TH-2 second material (film thickness 100 nm, second material concentration: 12% by mass)
  • a phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) is measured at a low temperature (77 [K]), and a tangent line is drawn with respect to the rising edge of the phosphorescence spectrum on the short wavelength side.
  • the energy amount calculated from the following conversion formula 2 was defined as an energy gap Eg 77K at 77 [K].
  • the spectrum measured in the same manner as described above includes light emission from both the excited singlet state and the excited triplet state, and it is difficult to distinguish clearly from which state the light is emitted.
  • the triplet energy value is considered dominant. Therefore, in the present embodiment, the measurement method is the same as that of the normal triplet energy EgT, but in order to distinguish the difference in strict meaning, the value measured as follows is referred to as an energy gap Eg 77K. .
  • EgS Singlet energy EgS is measured as follows. A 10 ⁇ mol / L toluene solution of the compound to be measured was prepared and placed in a quartz cell, and the absorption spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of this sample was measured at room temperature (300 K). A single line energy was calculated by drawing a tangent line to the long wavelength falling edge of the absorption spectrum and substituting the wavelength value ⁇ edge [nm] at the intersection of the tangent line and the horizontal axis into the following conversion formula 3. .
  • the difference between the singlet energy EgS and the energy gap Eg 77K is defined as ⁇ ST.
  • the ionization potential Ip (M3) of the third material and the ionization potential Ip (M2) of the second material satisfy the relationship of the following mathematical formula (Formula 4). By satisfying this relationship, it is possible to make the third material hardly participate in exciton generation and carrier transport in the light emitting layer. Ip (M3) ⁇ Ip (M2) (Equation 4)
  • the ionization potential Ip (M3) of the third material is preferably 6.3 eV or more.
  • the third material can be hardly involved in exciton generation and carrier transport in the light emitting layer.
  • the ionization potential can be measured using a photoelectron spectrometer in the atmosphere. Specifically, the measurement was performed by irradiating the material with light and measuring the amount of electrons generated by charge separation at that time.
  • the measuring device include a photoelectron spectrometer (device name: AC-3) manufactured by Riken Keiki Co., Ltd.
  • the electron affinity Af (M3) of the third material and the electron affinity Af (M2) of the second material satisfy the relationship of the following mathematical formula (Formula 5).
  • the third material hardly participate in exciton generation and carrier transport in the light emitting layer.
  • the third material preferably has an electron affinity Af (M3) of 6.3 eV or more.
  • M3 electron affinity Af
  • the electron affinity can be calculated from the following calculation formula (Formula 8) using the ionization potential Ip of the compound and the measured singlet energy EgS measured by the method described above.
  • Af Ip ⁇ EgS (Equation 8)
  • the film thickness of the light emitting layer in the organic EL device of the present embodiment is preferably 5 nm to 50 nm, more preferably 7 nm to 50 nm, and most preferably 10 nm to 50 nm. If the thickness is less than 5 nm, it is difficult to form a light emitting layer, and it may be difficult to adjust the chromaticity. If the thickness exceeds 50 nm, the driving voltage may increase.
  • the content rate of a 1st material is 0.01 to 10 mass% in a light emitting layer, and is 2nd material.
  • the content of is preferably 1% by mass or more and 75% by mass or less
  • the content of the third material is preferably 1% by mass or more and 75% by mass or less.
  • the upper limit of the total content of the first material, the second material, and the third material in the light emitting layer is 100% by mass.
  • this embodiment does not exclude that a material other than the first material, the second material, and the third material is included in the light emitting layer.
  • anode For the anode formed on the substrate, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a high work function (specifically, 4.0 eV or more). Specifically, for example, indium tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, and indium oxide containing zinc oxide. And graphene.
  • ITO indium tin oxide
  • ITO indium oxide-tin oxide containing silicon or silicon oxide
  • indium oxide-zinc oxide silicon oxide
  • tungsten oxide tungsten oxide
  • indium oxide containing zinc oxide and graphene.
  • Au gold
  • platinum (Pt) nickel
  • Ni tungsten
  • W chromium
  • Mo molybdenum
  • iron (Fe) iron
  • cobalt Co
  • copper copper
  • Pd palladium
  • Ti titanium
  • a metal material nitride for example, titanium nitride
  • indium oxide containing tungsten oxide and zinc oxide contains 0.5% by mass to 5% by mass of tungsten oxide and 0.1% by mass to 1% by mass of zinc oxide with respect to indium oxide.
  • a target it can be formed by a sputtering method.
  • the hole injection layer formed in contact with the anode is formed using a composite material that facilitates hole injection regardless of the work function of the anode.
  • any material that can be used as an electrode material for example, a metal, an alloy, an electrically conductive compound, and a mixture thereof, and other elements belonging to Group 1 or Group 2 of the periodic table
  • An element belonging to Group 1 or Group 2 of the periodic table which is a material having a low work function, that is, an alkali metal such as lithium (Li) or cesium (Cs), and magnesium (Mg), calcium (Ca), or strontium Alkaline earth metals such as (Sr), and alloys containing these (eg, MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these can also be used.
  • an alkali metal such as lithium (Li) or cesium (Cs)
  • Mg magnesium
  • Ca calcium
  • strontium Alkaline earth metals such as (Sr)
  • alloys containing these eg, MgAg, AlLi
  • rare earth metals such as europium (
  • an anode is formed using an alkali metal, an alkaline earth metal, and an alloy containing these
  • a vacuum evaporation method or a sputtering method can be used.
  • coating method, the inkjet method, etc. can be used.
  • cathode It is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a low work function (specifically, 3.8 eV or less) for the cathode.
  • cathode materials include elements belonging to Group 1 or Group 2 of the periodic table of elements, that is, alkali metals such as lithium (Li) and cesium (Cs), and magnesium (Mg) and calcium (Ca ), Alkaline earth metals such as strontium (Sr), and alloys containing these (for example, rare earth metals such as MgAg, AlLi), europium (Eu), ytterbium (Yb), and alloys containing these.
  • a vacuum evaporation method or a sputtering method can be used.
  • coating method, the inkjet method, etc. can be used.
  • a cathode is formed using various conductive materials such as indium oxide-tin oxide containing Al, Ag, ITO, graphene, silicon, or silicon oxide regardless of the work function. can do. These conductive materials can be formed by a sputtering method, an inkjet method, a spin coating method, or the like.
  • the hole injection layer is a layer containing a substance having a high hole injection property.
  • Substances with high hole injection properties include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, Tungsten oxide, manganese oxide, or the like can be used.
  • As a substance having a high hole-injecting property 4,4 ′, 4 ′′ -tris (N, N-diphenylamino) triphenylamine (abbreviation: TDATA), 4,4 ′, which is a low-molecular organic compound, is used.
  • a high molecular compound an oligomer, a dendrimer, a polymer, or the like
  • a high molecular compound an oligomer, a dendrimer, a polymer, or the like
  • PVK poly (N-vinylcarbazole)
  • PVTPA poly (4-vinyltriphenylamine)
  • PTPDMA poly [N- (4- ⁇ N ′-[4- (4-diphenylamino)] Phenyl] phenyl-N′-phenylamino ⁇ phenyl) methacrylamide]
  • PTPDMA poly [N, N′-bis (4-butylphenyl) -N, N′-bis (phenyl) benzidine]
  • High molecular compounds such as Poly-TPD
  • a polymer compound to which an acid such as poly (3,4-ethylenedioxythiophene) / poly (styrenesulfonic acid) (PEDOT / PSS), polyaniline / poly (styrenesulfonic acid) (PAni / PSS) is added is used. You can also.
  • the hole transport layer is a layer containing a substance having a high hole transport property.
  • An aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used for the hole transport layer.
  • NPB 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl
  • TPD diphenyl- [1,1′-biphenyl] -4,4′-diamine
  • BAFLP 4-phenyl-4 ′-(9-phenylfluoren-9-yl) triphenylamine
  • the substances mentioned here are mainly substances having a hole mobility of 10 ⁇ 6 cm 2 / (V ⁇ s) or more.
  • CBP 9- [4- (N-carbazolyl)] phenyl-10-phenylanthracene (CzPA), 9-phenyl-3- [4- (10-phenyl-9-anthryl) phenyl]
  • a carbazole derivative such as -9H-carbazole (PCzPA) or an anthracene derivative such as t-BuDNA, DNA, or DPAnth may be used.
  • a high molecular compound such as poly (N-vinylcarbazole) (abbreviation: PVK) or poly (4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.
  • PVK poly (N-vinylcarbazole)
  • PVTPA poly (4-vinyltriphenylamine)
  • the layer containing a substance having a high hole-transport property is not limited to a single layer, and two or more layers containing the above substances may be stacked.
  • a material having a larger energy gap is HT-2 used in Examples described later.
  • the electron transport layer is a layer containing a substance having a high electron transport property.
  • metal complexes such as aluminum complexes, beryllium complexes and zinc complexes
  • heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives and phenanthroline derivatives
  • 3) polymer compounds can be used.
  • Alq tris (4-methyl-8-quinolinolato) aluminum (abbreviation: Almq 3 ), bis (10-hydroxybenzo [h] quinolinato) beryllium (abbreviation: BeBq 2 ),
  • a metal complex such as BAlq, Znq, ZnPBO, ZnBTZ, or the like can be used.
  • a benzimidazole compound can be suitably used.
  • the substances described here are mainly substances having an electron mobility of 10 ⁇ 6 cm 2 / (V ⁇ s) or more.
  • any substance other than the above substances may be used for the electron-transport layer as long as it has a higher electron-transport property than the hole-transport property.
  • the electron transport layer may be composed of a single layer, or may be composed of two or more layers made of the above substances.
  • a high molecular compound can also be used for an electron carrying layer.
  • poly [(9,9-dihexylfluorene-2,7-diyl) -co- (pyridine-3,5-diyl)] (abbreviation: PF-Py)
  • poly [(9,9-dioctylfluorene-2) , 7-diyl) -co- (2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy) and the like can be used.
  • the electron injection layer is a layer containing a substance having a high electron injection property.
  • a substance having a high electron injection property lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), lithium oxide (LiOx), etc.
  • An alkali metal, an alkaline earth metal, or a compound thereof can be used.
  • a substance in which an alkali metal, an alkaline earth metal, or a compound thereof is contained in a substance having an electron transporting property specifically, a substance in which magnesium (Mg) is contained in Alq may be used. In this case, electron injection from the cathode can be performed more efficiently.
  • a composite material obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer.
  • a composite material is excellent in electron injecting property and electron transporting property because electrons are generated in the organic compound by the electron donor.
  • the organic compound is preferably a material excellent in transporting the generated electrons.
  • a substance (metal complex, heteroaromatic compound, or the like) constituting the electron transport layer described above is used. be able to.
  • the electron donor may be any substance that exhibits an electron donating property to the organic compound.
  • alkali metals, alkaline earth metals, and rare earth metals are preferable, and lithium, cesium, magnesium, calcium, erbium, ytterbium, and the like can be given.
  • Alkali metal oxides and alkaline earth metal oxides are preferable, and lithium oxide, calcium oxide, barium oxide, and the like can be given.
  • a Lewis base such as magnesium oxide can also be used.
  • an organic compound such as tetrathiafulvalene (abbreviation: TTF) can be used.
  • the method for forming each layer of the organic EL element of the present embodiment is not limited except as specifically mentioned above, but a dry film forming method such as a vacuum evaporation method, a sputtering method, a plasma method, an ion plating method, a spin method, Known methods such as a coating method, a dipping method, a flow coating method, and a wet film forming method such as an ink jet method can be employed.
  • the film thickness of each organic layer of the organic EL element of the present embodiment is not limited except as specifically mentioned above. Generally, if the film thickness is too thin, defects such as pinholes are likely to occur, and conversely, if it is too thick, it is high. Since an applied voltage is required and the efficiency is deteriorated, the range of several nm to 1 ⁇ m is usually preferable.
  • the number of ring-forming carbon atoms constitutes the ring itself of a compound having a structure in which atoms are bonded cyclically (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, or a heterocyclic compound). Represents the number of carbon atoms in the atom.
  • the carbon contained in the substituent is not included in the number of ring-forming carbons.
  • the “ring-forming carbon number” described below is the same unless otherwise specified.
  • the benzene ring has 6 ring carbon atoms
  • the naphthalene ring has 10 ring carbon atoms
  • the pyridinyl group has 5 ring carbon atoms
  • the furanyl group has 4 ring carbon atoms.
  • the carbon number of the alkyl group is not included in the number of ring-forming carbons.
  • the number of ring-forming atoms means a compound (for example, a monocyclic compound, a condensed ring compound, a bridging compound, a carbocyclic compound, a heterocyclic compound) having a structure in which atoms are bonded in a cyclic manner (for example, a monocyclic ring, a condensed ring, or a ring assembly).
  • a compound for example, a monocyclic compound, a condensed ring compound, a bridging compound, a carbocyclic compound, a heterocyclic compound having a structure in which atoms are bonded in a cyclic manner (for example, a monocyclic ring, a condensed ring, or a ring assembly).
  • a cyclic manner for example, a monocyclic ring, a condensed ring, or a ring assembly
  • An atom that does not constitute a ring for example, a hydrogen atom that terminates a bond of an atom that constitutes a ring
  • an atom contained in a substituent when the ring is substituted by a substituent is not included in the number of ring-forming atoms.
  • the “number of ring-forming atoms” described below is the same unless otherwise specified.
  • the pyridine ring has 6 ring atoms
  • the quinazoline ring has 10 ring atoms
  • the furan ring has 5 ring atoms.
  • a hydrogen atom bonded to a carbon atom of a pyridine ring or a quinazoline ring or an atom constituting a substituent is not included in the number of ring-forming atoms. Further, when, for example, a fluorene ring is bonded to the fluorene ring as a substituent (including a spirofluorene ring), the number of atoms of the fluorene ring as a substituent is not included in the number of ring-forming atoms.
  • each substituent described in the general formula will be described.
  • Examples of the aromatic hydrocarbon group having 6 to 30 ring carbon atoms in the present embodiment include a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a fluorenyl group, a pyrenyl group, a chrysenyl group, Fluoranthenyl group, benzo [a] anthryl group, benzo [c] phenanthryl group, triphenylenyl group, benzo [k] fluoranthenyl group, benzo [g] chrycenyl group, benzo [b] triphenylenyl group, picenyl group, perylenyl group Etc.
  • the aryl group preferably has 6 to 20 ring carbon atoms, and more preferably 6 to 12 carbon atoms.
  • a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a terphenyl group, and a fluorenyl group are particularly preferable.
  • heterocyclic group having 5 to 30 ring atoms examples include a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolyl group, an isoquinolinyl group, a naphthyridinyl group, and a phthalazinyl group.
  • the number of ring-forming atoms of the heterocyclic group is preferably 5-20, and more preferably 5-14.
  • the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms in the present embodiment or substitution is performed on the 9th-position nitrogen atom.
  • an unsubstituted heterocyclic group having 5 to 30 ring atoms is preferably substituted.
  • the heterocyclic group may be a group derived from a partial structure represented by the following general formulas (XY-1) to (XY-18), for example.
  • X and Y are each independently a hetero atom, preferably an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, or a germanium atom.
  • the partial structures represented by the general formulas (XY-1) to (XY-18) have a bond at an arbitrary position to be a heterocyclic group, and this heterocyclic group has a substituent. Also good.
  • the substituted or unsubstituted carbazolyl group may also include, for example, a group in which a ring is further condensed with respect to a carbazole ring represented by the following formula. Such a group may also have a substituent. Also, the position of the joint can be changed as appropriate.
  • the alkyl group having 1 to 30 carbon atoms may be linear, branched or cyclic.
  • the linear or branched alkyl group include a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl
  • the linear or branched alkyl group in the present embodiment preferably has 1 to 10 carbon atoms, and more preferably 1 to 6 carbon atoms.
  • An amyl group, an isoamyl group, and a neopentyl group are particularly preferable.
  • Examples of the cycloalkyl group in this embodiment include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, an adamantyl group, and a norbornyl group.
  • the number of carbon atoms forming the ring of the cycloalkyl group is preferably 3 to 10, and more preferably 5 to 8.
  • a cyclopentyl group and a cyclohexyl group are particularly preferable.
  • halogenated alkyl group in which the alkyl group is substituted with a halogen atom include those in which the alkyl group having 1 to 30 carbon atoms is substituted with one or more halogen groups. Specific examples include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, a trifluoromethylmethyl group, a trifluoroethyl group, and a pentafluoroethyl group.
  • alkylsilyl group having 3 to 30 carbon atoms in the present embodiment examples include a trialkylsilyl group having an alkyl group exemplified as the alkyl group having 1 to 30 carbon atoms, specifically, a trimethylsilyl group and a triethylsilyl group.
  • the three alkyl groups in the trialkylsilyl group may be the same or different.
  • Examples of the arylsilyl group having 6 to 30 ring carbon atoms in the present embodiment include a dialkylarylsilyl group, an alkyldiarylsilyl group, and a triarylsilyl group.
  • Examples of the dialkylarylsilyl group include a dialkylarylsilyl group having two alkyl groups exemplified as the alkyl group having 1 to 30 carbon atoms and one aryl group having 6 to 30 ring carbon atoms. .
  • the carbon number of the dialkylarylsilyl group is preferably 8-30.
  • alkyldiarylsilyl group examples include an alkyldiarylsilyl group having one alkyl group exemplified for the alkyl group having 1 to 30 carbon atoms and two aryl groups having 6 to 30 ring carbon atoms. .
  • the alkyldiarylsilyl group preferably has 13 to 30 carbon atoms.
  • Examples of the triarylsilyl group include a triarylsilyl group having three aryl groups having 6 to 30 ring carbon atoms.
  • the carbon number of the triarylsilyl group is preferably 18-30.
  • the alkoxy group having 1 to 30 carbon atoms in this embodiment is represented by —OZ 1 .
  • Z 1 include the above alkyl groups having 1 to 30 carbon atoms.
  • Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, and a hexyloxy group.
  • the alkoxy group preferably has 1 to 20 carbon atoms.
  • Examples of the halogenated alkoxy group in which the alkoxy group is substituted with a halogen atom include those in which the alkoxy group having 1 to 30 carbon atoms is substituted with one or more halogen groups.
  • the aryloxy group having 6 to 30 ring carbon atoms in the present embodiment is represented by —OZ 2 .
  • Z 2 include the aryl group having 6 to 30 ring carbon atoms.
  • the ring-forming carbon number of the aryloxy group is preferably 6-20.
  • Examples of the aryloxy group include a phenoxy group.
  • the alkylamino group having 2 to 30 carbon atoms is represented as —NHR V or —N (R V ) 2 .
  • Examples of RV include the alkyl group having 1 to 30 carbon atoms.
  • the arylamino group having 6 to 60 ring carbon atoms is represented by —NHR W or —N (R W ) 2 .
  • R W and an aryl group the ring-forming carbon atoms 6 to 30.
  • the alkylthio group having 1 to 30 carbon atoms is represented as —SR V.
  • RV include the alkyl group having 1 to 30 carbon atoms.
  • the alkylthio group preferably has 1 to 20 carbon atoms.
  • An arylthio group having 6 to 30 ring carbon atoms is represented by —SR W. Examples of R W, and an aryl group the ring-forming carbon atoms 6 to 30.
  • the ring-forming carbon number of the arylthio group is preferably 6-20.
  • ring-forming carbon means a carbon atom constituting a saturated ring, an unsaturated ring, or an aromatic ring.
  • Ring-forming atom means a carbon atom and a hetero atom constituting a hetero ring (including a saturated ring, an unsaturated ring, and an aromatic ring).
  • the hydrogen atom includes isotopes having different numbers of neutrons, that is, light hydrogen (Protium), deuterium (Deuterium), and tritium (Tritium).
  • the substituent in the present embodiment such as a substituent in the case of “substituted or unsubstituted”, a ring structure A, a ring structure B, a ring structure E, a ring structure F, a substituent in the ring structure G, etc.
  • an arylamino group, an alkylthio group, and an arylthio group an alkenyl group, an alkynyl group, an aralkyl group, a halogen atom, a cyano group, a hydroxyl group, a nitro group, and a carboxy group are exemplified.
  • an aryl group, a heterocyclic group, an alkyl group, a halogen atom, an alkylsilyl group, an arylsilyl group, and a cyano group are preferable, and further, specific examples that are preferable in the description of each substituent Are preferred.
  • These substituents may be further substituted with the above substituents. A plurality of these substituents may be bonded to each other to form a ring.
  • the alkenyl group is preferably an alkenyl group having 2 to 30 carbon atoms, which may be linear, branched or cyclic, such as a vinyl group, propenyl group, butenyl group, oleyl group, eicosapentaenyl group. , Docosahexaenyl group, styryl group, 2,2-diphenylvinyl group, 1,2,2-triphenylvinyl group, 2-phenyl-2-propenyl group, cyclopentadienyl group, cyclopentenyl group, cyclohexenyl group And cyclohexadienyl group.
  • the alkynyl group is preferably an alkynyl group having 2 to 30 carbon atoms and may be linear, branched or cyclic, and examples thereof include ethynyl, propynyl, 2-phenylethynyl and the like.
  • an aralkyl group having 6 to 30 ring carbon atoms is preferable, and is represented by —Z 3 —Z 4 .
  • Z 3 include an alkylene group corresponding to the alkyl group having 1 to 30 carbon atoms.
  • this Z 4 include the above aryl group having 6 to 30 ring carbon atoms.
  • This aralkyl group is an aralkyl group having 7 to 30 carbon atoms (the aryl moiety has 6 to 30 carbon atoms, preferably 6 to 20 carbon atoms, more preferably 6 to 12 carbon atoms), and the alkyl moiety has 1 to 30 carbon atoms (preferably 1 to 1 carbon atoms).
  • aralkyl group examples include benzyl group, 2-phenylpropan-2-yl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, and phenyl-t-butyl.
  • ⁇ -naphthylmethyl group 1- ⁇ -naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group, ⁇ -naphthylmethyl group, 1- ⁇ - Examples include naphthylethyl group, 2- ⁇ -naphthylethyl group, 1- ⁇ -naphthylisopropyl group, and 2- ⁇ -naphthylisopropyl group.
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a fluorine atom is preferred.
  • unsubstituted in the case of “substituted or unsubstituted” means that a hydrogen atom is bonded without being substituted with the substituent.
  • the “carbon number XX to YY” in the expression “substituted or unsubstituted ZZ group having XX to YY” represents the number of carbon atoms in the case where the ZZ group is unsubstituted. The carbon number of the substituent in the case where it is present is not included.
  • “YY” is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.
  • atom number XX to YY in the expression “a ZZ group having a substituted or unsubstituted atom number XX to YY” represents the number of atoms when the ZZ group is unsubstituted. In this case, the number of substituent atoms is not included.
  • YY is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.
  • the case of “substituted or unsubstituted” is the same as described above.
  • a multiple linking group in which 2 to 4 groups selected from the aromatic hydrocarbon groups are bonded and a multiple in which 2 to 4 groups selected from the heterocyclic groups are bonded.
  • Examples of a linking group or a multiple linking group formed by bonding two to four groups selected from the aromatic hydrocarbon group and the heterocyclic group include the aromatic hydrocarbon group and the heterocyclic group. Examples thereof include a divalent group formed by bonding 2 to 4 groups selected.
  • Examples of the multiple linking group formed by bonding 2 to 4 groups selected from the aromatic hydrocarbon group and the heterocyclic group include heterocyclic group-aromatic hydrocarbon group, aromatic hydrocarbon group-heterocycle Group, aromatic hydrocarbon group-heterocyclic group-aromatic hydrocarbon group, heterocyclic group-aromatic hydrocarbon group-heterocyclic group, aromatic hydrocarbon group-heterocyclic group-aromatic hydrocarbon group-heterocycle Group, heterocyclic group-aromatic hydrocarbon group-heterocyclic group-aromatic hydrocarbon group, and the like.
  • a divalent group formed by bonding the aromatic hydrocarbon group and the heterocyclic group one by one that is, a heterocyclic group-aromatic hydrocarbon group, and an aromatic hydrocarbon group-heterocyclic group.
  • Specific examples of the aromatic hydrocarbon group and the heterocyclic group in these multiple linking groups include the groups described above for the aromatic hydrocarbon group and the heterocyclic group.
  • the organic EL element according to this embodiment can be used for electronic devices.
  • the electronic device include a display device and a light emitting device.
  • the display device include display components such as an organic EL panel module, a television, a mobile phone, a tablet, and a personal computer.
  • the light emitting device include lighting and vehicle lamps.
  • the light emitting layer is not limited to one layer, and a plurality of light emitting layers may be stacked.
  • the organic EL element has a plurality of light emitting layers, it is sufficient that at least one light emitting layer contains the first material, the second material, and the third material, and the other light emitting layers emit fluorescent light.
  • a layer may be a phosphorescent light-emitting layer that utilizes light emission by electron transition from a triplet excited state directly to a ground state.
  • these light emitting layers may be provided adjacent to each other, or a so-called tandem organic material in which a plurality of light emitting units are stacked via an intermediate layer. It may be an EL element.
  • a barrier layer may be provided adjacent to the anode side or the cathode side of the light emitting layer.
  • the barrier layer is preferably disposed in contact with the light emitting layer and blocks at least one of holes, electrons, excitons, and exciplexes.
  • the barrier layer transports electrons, and the holes reach a layer (for example, an electron transport layer) on the cathode side of the barrier layer. Stop that.
  • a barrier layer when a barrier layer is disposed in contact with the anode side of the light emitting layer, the barrier layer transports holes, and the electrons reach a layer on the anode side of the barrier layer (for example, a hole transport layer). To stop doing.
  • a barrier layer may be provided adjacent to the light emitting layer so that excitation energy does not leak from the light emitting layer to the peripheral layer. The excitons generated in the light emitting layer are prevented from moving to a layer (for example, an electron transport layer or a hole transport layer) closer to the electrode than the barrier layer.
  • the light emitting layer and the barrier layer are preferably joined.
  • the compounds used in this example are as follows.
  • EgS Singlet energy
  • a 10 ⁇ mol / L toluene solution of the compound to be measured was prepared and placed in a quartz cell, and the absorption spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of this sample was measured at room temperature (300 K).
  • a single line energy was calculated by drawing a tangent line to the long wavelength falling edge of the absorption spectrum and substituting the wavelength value ⁇ edge [nm] at the intersection of the tangent line and the horizontal axis into the following conversion formula 3. .
  • Conversion formula 3: EgS [eV] 1239.85 / ⁇ edge
  • the absorption spectrum was measured with a spectrophotometer manufactured by Hitachi (device name: U3310).
  • the tangent with respect to the fall of the long wavelength side of an absorption spectrum was drawn as follows.
  • the tangent at each point on the curve is considered. This tangent repeats as the curve falls (ie, as the value on the vertical axis decreases), the slope decreases and then increases.
  • the tangent drawn at the point where the slope value takes the minimum value on the long wavelength side is taken as the tangent to the fall on the long wavelength side of the absorption spectrum.
  • the maximum point whose absorbance value is 0.2 or less was not included in the maximum value on the longest wavelength side.
  • the triplet energy was measured as follows.
  • Compound MT-1 and Compound MT-3 were measured.
  • a phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) is measured at a low temperature (77 [K]), and a tangent line is drawn with respect to the rising edge of the phosphorescence spectrum on the short wavelength side.
  • the energy amount calculated from the following conversion formula 1 was defined as an energy gap Eg 77K at 77 [K].
  • Conversion formula 1: Eg 77K [eV] 1239.85 / ⁇ edge
  • the triplet energy was measured as follows.
  • the compound MT-2 was used as the measurement target.
  • a sample (second material) to be measured and the compound TH-2 were co-deposited on a quartz substrate, and a sample sealed in an NMR tube was produced.
  • This sample was produced under the following conditions. Quartz substrate / TH-2: second material (film thickness 100 nm, second material concentration: 12% by mass)
  • Quartz substrate / TH-2 second material (film thickness 100 nm, second material concentration: 12% by mass)
  • a phosphorescence spectrum vertical axis: phosphorescence emission intensity, horizontal axis: wavelength
  • a tangent line is drawn with respect to the rising edge of the phosphorescence spectrum on the short wavelength side.
  • the tangent to the rising edge on the short wavelength side of the phosphorescence spectrum is drawn as follows. When moving on the spectrum curve from the short wavelength side of the phosphorescence spectrum to the maximum value on the shortest wavelength side among the maximum values of the spectrum, tangents at each point on the curve are considered toward the long wavelength side. The slope of this tangent line increases as the curve rises (that is, as the vertical axis increases). A tangent drawn at a point where the value of the slope takes a maximum value (that is, a tangent at the inflection point) is a tangent to the rising edge of the phosphorescence spectrum on the short wavelength side.
  • the maximum point having a peak intensity of 15% or less of the maximum peak intensity of the spectrum is not included in the above-mentioned maximum value on the shortest wavelength side, and has the maximum slope value closest to the maximum value on the shortest wavelength side.
  • the tangent drawn at the point where the value was taken was taken as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side.
  • an F-4500 spectrofluorometer main body manufactured by Hitachi High-Technology Co., Ltd. was used for the phosphorescence measurement.
  • Delayed fluorescence emission was confirmed by measuring transient PL using the apparatus shown in FIG.
  • the compound MT-2 and the compound TH-2 were co-evaporated on a quartz substrate so that the ratio of the compound MT-2 was 12% by mass, and a thin film having a thickness of 100 nm was formed to prepare a sample.
  • Delayed fluorescence can be obtained using the apparatus shown in FIG. Prompt light emission (immediate light emission) immediately observed from the excited state after excitation with pulsed light (light irradiated from a pulse laser) of a wavelength absorbed by the compound MT-2, and immediately after the excitation Is not observed, and there is delay light emission (delayed light emission) observed thereafter.
  • the delayed fluorescence emission in this example means that the amount of delay emission (delayed emission) is 5% or more with respect to the amount of Promp emission (immediate emission), and the compound MT-2 has an amount of delay emission (delayed emission). Is 5% or more of the amount of Prompt light emission (immediate light emission).
  • the amounts of Prompt light emission and Delay light emission can be obtained by a method similar to the method described in “Nature 492, 234-238, 2012”.
  • the apparatus used for calculation of the amount of Promp light emission and Delay light emission is not limited to the apparatus shown in the said FIG. 2, or the apparatus of the said reference literature 1.
  • FIG. 1 the apparatus used for calculation of the amount of Promp light emission and Delay light emission is not limited to the apparatus shown in the said FIG. 2, or the apparatus of the said reference literature 1.
  • Example 1 A glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anode) having a thickness of 25 mm ⁇ 75 mm ⁇ 1.1 mm was subjected to ultrasonic cleaning for 5 minutes in isopropyl alcohol, and then UV ozone cleaning was performed for 30 minutes.
  • the film thickness of ITO was 130 nm.
  • the glass substrate with the transparent electrode line after the cleaning is mounted on the substrate holder of the vacuum deposition apparatus, and first, the compound HI is deposited so as to cover the transparent electrode on the surface where the transparent electrode line is formed, and the film thickness is 5 nm.
  • the hole injection layer was formed.
  • Compound HT-1 was vapor-deposited on the hole injection layer, and a first hole transport layer having a thickness of 80 nm was formed on the HI film.
  • Compound HT-2 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a thickness of 15 nm. Further, on this second hole transport layer, the compound MT-1 as the first material, the compound MT-2 as the second material, and the compound MT-3 as the third material are combined. Evaporation was performed to form a light emitting layer with a thickness of 25 nm.
  • the concentration of compound MT-1 in the light emitting layer was 1% by mass, the concentration of compound MT-2 was 50% by mass, and the concentration of compound MT-3 was 49% by mass.
  • Compound HB-1 was vapor-deposited on the light emitting layer to form a 5 nm thick barrier layer.
  • Compound ET-1 was vapor-deposited on this barrier layer to form an electron transport layer having a thickness of 20 nm.
  • lithium fluoride (LiF) was vapor-deposited on the electron transport layer to form an electron injecting electrode (cathode) having a thickness of 1 nm.
  • metal aluminum (Al) was vapor-deposited on this electron injecting electrode, and the metal Al cathode with a film thickness of 80 nm was formed.
  • a device arrangement of the organic EL device of Example 1 is schematically shown as follows.
  • Comparative Example 1 In the organic EL device of Comparative Example 1, instead of the light emitting layer in Example 1, the compound MT-1 as the first material and the compound MT-2 as the second material were co-evaporated to have a film thickness of 25 nm. This was prepared in the same manner as in Example 1 except that the light emitting layer was formed. In the light emitting layer of the organic EL device of Comparative Example 1, the concentration of the compound MT-1 in the light emitting layer was 1% by mass, and the concentration of the compound MT-2 was 99% by mass.
  • a device arrangement of the organic EL device of Comparative Example 1 is schematically shown as follows.
  • the voltage (unit: V) was measured when current was passed between the ITO transparent electrode and the metal Al cathode so that the current density was 0.1 mA / cm 2 , 1 mA / cm 2 or 10 mA / cm 2 . .
  • Luminance and CIE1931 chromaticity Luminance and CIE1931 chromaticity coordinates (x, y) when a voltage is applied to the device so that the current density is 0.1 mA / cm 2 , 1 mA / cm 2, or 10 mA / cm 2 was measured using a spectral radiance meter CS-1000 (manufactured by Konica Minolta Co., Ltd.).
  • Main peak wavelength ⁇ p was determined from the obtained spectral radiance spectrum.
  • Example 1 As shown in Table 6, when the organic EL element according to Example 1 was driven at any current density, compared with the organic EL element according to Comparative Example 1, the current efficiency L / J, the power efficiency ⁇ , and External quantum efficiency EQE became high.
  • the light emitting efficiency is low because the light emitting layer contains only the first material and the second material.
  • the organic EL device according to Example 1 not only the first material and the second material but also the third material was contained in the light emitting layer, so that the luminous efficiency was improved as compared with Comparative Example 1. it is conceivable that.
  • the wavelength was shorter than that in Comparative Example 1, and light emission with strong bluish color was observed. That is, it is considered that it is caused by dispersing the second material.
  • Example 1 was able to provide an organic EL element that emits blue light with high efficiency.
  • Example 2 A glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anode) having a thickness of 25 mm ⁇ 75 mm ⁇ 1.1 mm was subjected to ultrasonic cleaning for 5 minutes in isopropyl alcohol, and then UV ozone cleaning was performed for 30 minutes.
  • the film thickness of ITO was 70 nm.
  • the glass substrate with the transparent electrode line after the cleaning is mounted on the substrate holder of the vacuum deposition apparatus, and first, the compound HI is deposited so as to cover the transparent electrode on the surface where the transparent electrode line is formed, and the film thickness is 5 nm.
  • the hole injection layer was formed.
  • Compound HT-1 was vapor-deposited on the hole injection layer, and a first hole transport layer having a thickness of 65 nm was formed on the HI film.
  • Compound HT-2 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a thickness of 10 nm.
  • Compound MT-4, Compound MT-9, and Compound MT-10 were co-evaporated on the second hole transport layer to form a light emitting layer having a thickness of 25 nm.
  • the concentration of compound MT-10 in the light emitting layer was 1% by mass, the concentration of compound MT-9 was 50% by mass, and the concentration of compound MT-4 was 49% by mass.
  • Compound HB-2 was vapor-deposited on the light emitting layer to form a barrier layer having a thickness of 5 nm.
  • Compound ET-1 was vapor-deposited on this barrier layer to form an electron transport layer having a thickness of 30 nm.
  • lithium fluoride (LiF) was vapor-deposited on the electron transport layer to form an electron injecting electrode (cathode) having a thickness of 1 nm.
  • metal aluminum (Al) was vapor-deposited on this electron injecting electrode, and the metal Al cathode with a film thickness of 80 nm was formed.
  • a device arrangement of the organic EL device of Example 2 is schematically shown as follows.
  • Example 4 The organic EL device of Example 4 was produced in the same manner as Example 2 except that Compound MT-5 was used instead of Compound MT-4 in the light emitting layer of Example 2.
  • a device arrangement of the organic EL device of Example 4 is schematically shown as follows. ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-5: MT-9: MT-10 (25, 49%: 50%: 1%) / HB- 2 (5) / ET-1 (30) / LiF (1) / Al (80)
  • Example 5 The organic EL device of Example 5 was produced in the same manner as Example 2 except that Compound MT-7 was used instead of Compound MT-4 in the light emitting layer of Example 2.
  • a device arrangement of the organic EL device of Example 5 is schematically shown as follows. ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-7: MT-9: MT-10 (25, 49%: 50%: 1%) / HB- 2 (5) / ET-1 (30) / LiF (1) / Al (80)
  • Example 6 The organic EL device of Example 6 was produced in the same manner as Example 2 except that Compound MT-8 was used instead of Compound MT-4 in the light emitting layer of Example 2.
  • a device arrangement of the organic EL device of Example 6 is schematically shown as follows. ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-8: MT-9: MT-10 (25, 49%: 50%: 1%) / HB- 2 (5) / ET-1 (30) / LiF (1) / Al (80)
  • Example 7 The organic EL device of Example 7 was produced in the same manner as Example 2 except that Compound HB-3 was used instead of Compound HB-2 in the barrier layer of Example 2.
  • a device arrangement of the organic EL device of Example 7 is schematically shown as follows. ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-4: MT-9: MT-10 (25, 49%: 50%: 1%) / HB- 3 (5) / ET-1 (30) / LiF (1) / Al (80)
  • Example 8 The organic EL device of Example 8 was produced in the same manner as in Example 7 except that Compound MT-6 was used instead of Compound MT-4 in the light emitting layer of Example 7.
  • a device arrangement of the organic EL device of Example 8 is schematically shown as follows. ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-6: MT-9: MT-10 (25, 49%: 50%: 1%) / HB- 3 (5) / ET-1 (30) / LiF (1) / Al (80)
  • Example 9 The organic EL device of Example 9 was produced in the same manner as in Example 7 except that Compound MT-5 was used instead of Compound MT-4 in the light emitting layer of Example 7.
  • a device arrangement of the organic EL device of Example 9 is schematically shown as follows. ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-5: MT-9: MT-10 (25, 49%: 50%: 1%) / HB- 3 (5) / ET-1 (30) / LiF (1) / Al (80)
  • Example 10 The organic EL device of Example 10 was produced in the same manner as in Example 7 except that Compound MT-7 was used instead of Compound MT-4 in the light emitting layer of Example 7.
  • a device arrangement of the organic EL device of Example 10 is schematically shown as follows. ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-7: MT-9: MT-10 (25, 49%: 50%: 1%) / HB- 3 (5) / ET-1 (30) / LiF (1) / Al (80)
  • Example 3 The organic EL device of Comparative Example 3 was the same as that of Example 7 except that instead of the light-emitting layer in Example 7, compound MT-9 and compound MT-10 were co-evaporated to form a light-emitting layer with a thickness of 25 nm. This was prepared in the same manner as in Example 7.
  • the concentration of compound MT-10 in the light emitting layer was 1% by mass, and the concentration of compound MT-9 was 99% by mass.
  • a device arrangement of the organic EL device of Comparative Example 3 is schematically shown as follows.
  • the organic EL elements of Examples 7 to 11 had higher luminous efficiency than the organic EL element of Comparative Example 3.
  • the organic EL device of Comparative Example 3 only includes compound MT-9 and compound MT-10 in the light emitting layer.
  • the organic EL elements of Examples 7 to 11 further contained a third material in the light emitting layer.
  • compound MT-4 is used in Example 7
  • compound MT-6 is used in Example 8
  • compound MT-5 is used in Example 9
  • compound MT-7 is used in Example 10
  • compound MT-7 is used in Example 11.
  • MT-8 was contained in the light emitting layer as a third material.
  • the organic EL elements of Examples 7 to 11 had higher current efficiency and external quantum efficiency than the organic EL element of Comparative Example 3.
  • Example 12 The organic EL device of Example 12 was produced in the same manner as in Example 2 except that Compound MT-11 was used instead of Compound MT-10 in the light emitting layer of Example 2.
  • a device arrangement of the organic EL device of Example 12 is schematically shown as follows. ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-4: MT-9: MT-11 (25, 49%: 50%: 1%) / HB- 2 (5) / ET-1 (30) / LiF (1) / Al (80)
  • Example 13 The organic EL device of Example 13 was produced in the same manner as in Example 12 except that Compound MT-6 was used instead of Compound MT-4 in the light emitting layer of Example 12.
  • a device arrangement of the organic EL device of Example 13 is schematically shown as follows. ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-6: MT-9: MT-11 (25, 49%: 50%: 1%) / HB- 2 (5) / ET-1 (30) / LiF (1) / Al (80)
  • Example 15 The organic EL device of Example 15 was produced in the same manner as in Example 12 except that Compound MT-8 was used instead of Compound MT-4 in the light emitting layer of Example 12.
  • a device arrangement of the organic EL device of Example 15 is schematically shown as follows. ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-8: MT-9: MT-11 (25, 49%: 50%: 1%) / HB- 2 (5) / ET-1 (30) / LiF (1) / Al (80)
  • Comparative Example 4 The organic EL device of Comparative Example 4 was the same as that of Example 12 except that instead of the light emitting layer in Example 12, compound MT-9 and compound MT-11 were co-evaporated to form a light emitting layer having a thickness of 25 nm. This was prepared in the same manner as in No. 12.
  • the concentration of Compound MT-10 in the light emitting layer was 1% by mass, and the concentration of Compound MT-11 was 99% by mass.
  • a device arrangement of the organic EL device of Comparative Example 4 is schematically shown as follows.
  • the organic EL elements of Examples 12 to 15 had higher luminous efficiency than the organic EL element of Comparative Example 4.
  • the organic EL device of Comparative Example 4 only includes compound MT-9 and compound MT-11 in the light emitting layer.
  • the organic EL elements of Examples 12 to 15 further contained a third material in the light emitting layer. Specifically, the compound MT-4 in Example 12, the compound MT-6 in Example 13, the compound MT-7 in Example 14, the compound MT-8 in Example 15, and the third material, respectively. In the light emitting layer.
  • the organic EL devices of Examples 12 to 15 had higher current efficiency and external quantum efficiency than the organic EL device of Comparative Example 4.
  • Example 16 The organic EL device of Example 16 was produced in the same manner as in Example 12 except that Compound HB-3 was used instead of Compound HB-2 in the barrier layer of Example 12.
  • a device arrangement of the organic EL device of Example 16 is schematically shown as follows. ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-4: MT-9: MT-11 (25, 49%: 50%: 1%) / HB- 3 (5) / ET-1 (30) / LiF (1) / Al (80)
  • Example 17 The organic EL device of Example 17 was produced in the same manner as in Example 16 except that Compound MT-6 was used instead of Compound MT-4 in the light emitting layer of Example 16.
  • a device arrangement of the organic EL device of Example 17 is schematically shown as follows. ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-6: MT-9: MT-11 (25, 49%: 50%: 1%) / HB- 3 (5) / ET-1 (30) / LiF (1) / Al (80)
  • Example 18 The organic EL device of Example 18 was produced in the same manner as in Example 16 except that Compound MT-7 was used instead of Compound MT-4 in the light emitting layer of Example 16.
  • a device arrangement of the organic EL device of Example 18 is schematically shown as follows. ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-7: MT-9: MT-11 (25, 49%: 50%: 1%) / HB- 3 (5) / ET-1 (30) / LiF (1) / Al (80)
  • Example 19 The organic EL device of Example 19 was produced in the same manner as in Example 16 except that Compound MT-8 was used instead of Compound MT-4 in the light emitting layer of Example 16.
  • a device arrangement of the organic EL device of Example 19 is schematically shown as follows. ITO (70) / HI (5) / HT-1 (65) / HT-2 (10) / MT-8: MT-9: MT-11 (25, 49%: 50%: 1%) / HB- 3 (5) / ET-1 (30) / LiF (1) / Al (80)
  • Example 5 The organic EL device of Comparative Example 5 was the same as in Example 16 except that instead of the light-emitting layer in Example 16, compound MT-9 and compound MT-11 were co-evaporated to form a light-emitting layer with a thickness of 25 nm. 16 was produced in the same manner.
  • the concentration of the compound MT-9 in the light emitting layer was 1% by mass, and the concentration of the compound MT-11 was 99% by mass.
  • a device arrangement of the organic EL device of Comparative Example 5 is schematically shown as follows.
  • the organic EL elements of Examples 16 to 19 had higher luminous efficiency than the organic EL element of Comparative Example 5.
  • the organic EL device of Comparative Example 5 only includes compound MT-9 and compound MT-11 in the light emitting layer.
  • the organic EL elements of Examples 16 to 19 further contained a third material in the light emitting layer. Specifically, the compound MT-4 in Example 16, the compound MT-6 in Example 17, the compound MT-7 in Example 18, the compound MT-8 in Example 19, and the third material, respectively. In the light emitting layer.
  • the organic EL elements of Examples 16 to 19 had higher current efficiency and external quantum efficiency than the organic EL element of Comparative Example 5.
  • Example 20 A glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anode) having a thickness of 25 mm ⁇ 75 mm ⁇ 1.1 mm was subjected to ultrasonic cleaning for 5 minutes in isopropyl alcohol, and then UV ozone cleaning was performed for 30 minutes.
  • the film thickness of ITO was 70 nm.
  • the glass substrate with the transparent electrode line after the cleaning is mounted on the substrate holder of the vacuum deposition apparatus, and first, the compound HI is deposited so as to cover the transparent electrode on the surface where the transparent electrode line is formed, and the film thickness is 5 nm.
  • the hole injection layer was formed.
  • Compound HT-1 was vapor-deposited on the hole injection layer, and a first hole transport layer having a thickness of 65 nm was formed on the HI film.
  • Compound HT-2 was vapor-deposited on the first hole transport layer to form a second hole transport layer having a thickness of 5 nm.
  • a compound CBP was vapor-deposited on the second hole transport layer to form a first barrier layer having a thickness of 5 nm.
  • Compound MT-13, Compound MT-12, and Compound MT-10 were co-evaporated on the first barrier layer to form a light emitting layer with a thickness of 25 nm.
  • the concentration of compound MT-10 in the light emitting layer was 1% by mass, the concentration of compound MT-12 was 50% by mass, and the concentration of compound MT-13 was 49% by mass.
  • Compound HB-2 was vapor-deposited on the light emitting layer to form a second barrier layer having a thickness of 5 nm.
  • Compound ET-1 was vapor-deposited on this second barrier layer to form an electron transport layer having a thickness of 30 nm.
  • lithium fluoride (LiF) was vapor-deposited on the electron transport layer to form an electron injecting electrode (cathode) having a thickness of 1 nm.
  • a device arrangement of the organic EL device of Example 20 is roughly shown as follows. ITO (70) / HI (5) / HT-1 (65) / HT-2 (5) / CBP (5) / MT-13: MT-12: MT-10 (25, 49%: 50%: 1 %) / HB-2 (5) / ET-1 (30) / LiF (1) / Al (80)
  • Example 21 In the organic EL device of Example 21, the concentration of the compound contained in the light emitting layer of Example 20 was 1% by mass of Compound MT-10, 25% by mass of Compound MT-12, and 25% by mass of Compound MT-13. It was produced in the same manner as in Example 20 except that the concentration was 74% by mass.
  • a device arrangement of the organic EL device of Example 21 is roughly shown as follows. ITO (70) / HI (5) / HT-1 (65) / HT-2 (5) / CBP (5) / MT-13: MT-12: MT-10 (25, 74%: 25%: 1 %) / HB-2 (5) / ET-1 (30) / LiF (1) / Al (80)
  • Example 22 In the organic EL device of Example 22, the compound MT-5 was used instead of the compound MT-13 in the light emitting layer of Example 20, and the concentration of the compound MT-10 was 1% by mass with respect to the concentration of the compound contained in the light emitting layer. This was prepared in the same manner as in Example 20 except that the concentration of compound MT-12 was 24 mass% and the concentration of compound MT-5 was 75 mass%.
  • a device arrangement of the organic EL device of Example 22 is roughly shown as follows.
  • Example 6 The organic EL device of Comparative Example 6 was the same as in Example 20 except that instead of the light emitting layer in Example 20, compound MT-12 and compound MT-10 were co-evaporated to form a light emitting layer having a thickness of 25 nm. 20 was prepared in the same manner as in No. 20. In the light emitting layer of the organic EL device of Comparative Example 6, the concentration of Compound MT-10 in the light emitting layer was 1% by mass, and the concentration of Compound MT-12 was 99% by mass.
  • a device arrangement of the organic EL device of Comparative Example 6 is schematically shown as follows.
  • the organic EL elements of Examples 20 to 22 had higher luminous efficiency than the organic EL element of Comparative Example 6.
  • the organic EL device of Comparative Example 6 only includes compound MT-10 and compound MT-12 in the light emitting layer.
  • the organic EL elements of Examples 20 to 22 further contained a third material in the light emitting layer.
  • Example 20 and 21 contained Compound MT-13 and Example 22 contained Compound MT-5 as the third material in the light emitting layer.
  • the organic EL elements of Examples 20 to 22 had higher current efficiency, power efficiency, and external quantum efficiency than the organic EL elements of Comparative Example 6.
  • Example 23 The organic EL device of Example 23 was produced in the same manner as in Example 20 except that Compound HB-3 was used instead of Compound HB-2 in the barrier layer of Example 20.
  • a device arrangement of the organic EL device of Example 23 is roughly shown as follows. ITO (70) / HI (5) / HT-1 (65) / HT-2 (5) / CBP (5) / MT-13: MT-12: MT-10 (25, 49%: 50%: 1 %) / HB-3 (5) / ET-1 (30) / LiF (1) / Al (80)
  • Example 24 In the organic EL device of Example 24, regarding the concentration of the compound contained in the light emitting layer of Example 23, the concentration of Compound MT-10 was 1% by mass, the concentration of Compound MT-12 was 25% by mass, It was produced in the same manner as in Example 23 except that the concentration was 74% by mass.
  • a device arrangement of the organic EL device of Example 24 is roughly shown as follows. ITO (70) / HI (5) / HT-1 (65) / HT-2 (5) / CBP (5) / MT-13: MT-12: MT-10 (25, 74%: 25%: 1 %) / HB-3 (5) / ET-1 (30) / LiF (1) / Al (80)
  • Example 25 The organic EL device of Example 25 uses Compound MT-5 instead of Compound MT-13 in the light emitting layer of Example 23, and the concentration of Compound MT-10 is 1% by mass with respect to the concentration of the compound contained in the light emitting layer. This was prepared in the same manner as in Example 23 except that the concentration of compound MT-12 was 24 mass% and the concentration of compound MT-5 was 75 mass%.
  • a device arrangement of the organic EL device of Example 25 is schematically shown as follows.
  • Example 7 The organic EL device of Comparative Example 7 was the same as in Example 23 except that instead of the light emitting layer in Example 23, compound MT-12 and compound MT-10 were co-evaporated to form a light emitting layer having a thickness of 25 nm. This was prepared in the same manner as in No.23. In the light emitting layer of the organic EL device of Comparative Example 7, the concentration of Compound MT-10 in the light emitting layer was 1% by mass, and the concentration of Compound MT-12 was 99% by mass.
  • a device arrangement of the organic EL device of Comparative Example 7 is schematically shown as follows.
  • the organic EL elements of Examples 23 to 25 had higher luminous efficiency than the organic EL element of Comparative Example 7.
  • the organic EL device of Comparative Example 7 only includes compound MT-10 and compound MT-12 in the light emitting layer.
  • the organic EL elements of Examples 23 to 25 further contained a third material in the light emitting layer.
  • Example 23 and 24 contained Compound MT-13 and Example 25 contained Compound MT-5 as the third material in the light emitting layer.
  • the organic EL elements of Examples 23 to 25 had higher current efficiency, power efficiency, and external quantum efficiency than the organic EL elements of Comparative Example 7.
  • Example 26 In the organic EL device of Example 26, the compound MT-11 was used instead of the compound MT-10 in the light emitting layer of Example 20, and the concentration of the compound MT-11 was 1% by mass with respect to the concentration of the compound contained in the light emitting layer. This was prepared in the same manner as in Example 20 except that the concentration of compound MT-12 was 25 mass% and the concentration of compound MT-13 was 74 mass%. A device arrangement of the organic EL device of Example 26 is roughly shown as follows.
  • Comparative Example 8 The organic EL device of Comparative Example 8 was prepared in the same manner as in Example 26 except that instead of the light emitting layer in Example 26, compound MT-12 and compound MT-11 were co-evaporated to form a light emitting layer having a thickness of 25 nm. 26.
  • the concentration of the compound MT-11 in the light emitting layer was 1% by mass, and the concentration of the compound MT-12 was 99% by mass.
  • a device arrangement of the organic EL device of Comparative Example 8 is schematically shown as follows.
  • the organic EL element of Example 26 had higher luminous efficiency than the organic EL element of Comparative Example 8.
  • the organic EL device of Comparative Example 8 only includes compound MT-11 and compound MT-12 in the light emitting layer. Compared to the organic EL element of Comparative Example 8, the organic EL element of Example 26 further contained compound MT-13 in the light emitting layer. As a result, the organic EL element of Example 26 had higher current efficiency, power efficiency, and external quantum efficiency than the organic EL element of Comparative Example 8.
  • Example 27 The organic EL device of Example 27 was produced in the same manner as in Example 26 except that Compound HB-3 was used instead of Compound HB-2 in the barrier layer of Example 26.
  • a device arrangement of the organic EL device of Example 27 is roughly shown as follows. ITO (70) / HI (5) / HT-1 (65) / HT-2 (5) / CBP (5) / MT-13: MT-12: MT-11 (25, 74%: 25%: 1 %) / HB-3 (5) / ET-1 (30) / LiF (1) / Al (80)
  • Comparative Example 9 The organic EL device of Comparative Example 9 was the same as that of Example 27 except that instead of the light emitting layer in Example 27, compound MT-12 and compound MT-11 were co-evaporated to form a light emitting layer with a thickness of 25 nm. This was prepared in the same manner as in No.27. In the light emitting layer of the organic EL device of Comparative Example 9, the concentration of the compound MT-11 in the light emitting layer was 1% by mass, and the concentration of the compound MT-12 was 99% by mass.
  • a device arrangement of the organic EL device of Comparative Example 9 is schematically shown as follows.
  • the organic EL element of Example 27 had higher luminous efficiency than the organic EL element of Comparative Example 9.
  • the organic EL device of Comparative Example 9 only includes compound MT-11 and compound MT-12 in the light emitting layer. Compared to the organic EL element of Comparative Example 9, the organic EL element of Example 27 further contained compound MT-13 in the light emitting layer. As a result, the organic EL device of Example 27 had higher current efficiency, power efficiency, and external quantum efficiency than the organic EL device of Comparative Example 9.
  • SYMBOLS 1 Organic EL element, 2 ... Substrate, 3 ... Anode, 4 ... Cathode, 5 ... Light emitting layer, 6 ... Hole injection / transport layer, 7 ... Electron injection / transport layer, 10 ... Organic layer.

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EP2958158A4 (en) 2016-09-28
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US20200395552A1 (en) 2020-12-17
CN106848074A (zh) 2017-06-13
US20230126981A1 (en) 2023-04-27
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US20180130959A1 (en) 2018-05-10
US9905779B2 (en) 2018-02-27
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CN105103326A (zh) 2015-11-25
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