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WO2017065295A1 - Élément électroluminescent organique et dispositif électronique - Google Patents

Élément électroluminescent organique et dispositif électronique Download PDF

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WO2017065295A1
WO2017065295A1 PCT/JP2016/080601 JP2016080601W WO2017065295A1 WO 2017065295 A1 WO2017065295 A1 WO 2017065295A1 JP 2016080601 W JP2016080601 W JP 2016080601W WO 2017065295 A1 WO2017065295 A1 WO 2017065295A1
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substituted
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carbon atoms
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Japanese (ja)
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俊成 荻原
圭 吉田
祐一郎 河村
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Idemitsu Kosan Co Ltd
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Idemitsu Kosan Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to an organic electroluminescence element and an electronic device.
  • organic electroluminescence element When a voltage is applied to an organic electroluminescence element (hereinafter sometimes referred to as “organic EL element”), holes from the anode and electrons from the cathode are injected into the light emitting layer. Then, in the light emitting layer, the injected holes and electrons are recombined to form excitons. At this time, singlet excitons and triplet excitons are generated at a ratio of 25%: 75% according to the statistical rule of electron spin. Fluorescent organic EL elements that use light emitted from singlet excitons are being applied to full-color displays such as mobile phones and televisions, but the internal quantum efficiency of 25% is said to be the limit. In addition to singlet excitons, triplet excitons are used, and organic EL devices are expected to emit light more efficiently.
  • organic EL element organic electroluminescence element
  • TADF Thermally Activated Delayed Fluorescence, heat activated delayed fluorescence
  • ⁇ ST small energy difference
  • Non-Patent Document 1 An organic EL element using this TADF mechanism is disclosed in Non-Patent Document 1, for example.
  • An organic EL element using the TADF mechanism is also disclosed in Patent Document 1, for example.
  • Patent Document 1 relates to an organic EL element that emits light mainly from a delayed fluorescent material in a light emitting layer.
  • the objective of this invention is providing the organic electroluminescent element which can improve luminous efficiency and can improve color purity, and an electronic device provided with the said organic electroluminescent element.
  • the light-emitting layer includes an anode, a light-emitting layer, and a cathode, and the light-emitting layer includes a delayed fluorescent first compound represented by the following general formula (1) and a fluorescent light-emitting property.
  • An organic electroluminescent device comprising the second compound is provided.
  • X is an oxygen atom, a sulfur atom, or a selenium atom
  • Y 1 to Y 8 are each independently CR 1a , CR 1b , or a nitrogen atom, provided that Y 1 To Y 8 are nitrogen atoms, and at least one of Y 1 to Y 8 is CR 1a
  • R 1a is independently represented by the following general formulas (A) to (N): is any group selected from the group consisting of that group, if R 1a there are a plurality, the plurality of R 1a may be the same or different from each other
  • R 1b each independently represent a hydrogen atom or R 1b as a substituent is each independently a halogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted group Or leave Substituted aralky
  • X 1 to X 20 are each independently a nitrogen atom or CRx, provided that in the general formula (B), any one of X 5 to X 8 is is a carbon atom bonded with any of X 9 ⁇ X 12, any of X 9 ⁇ X 12, a carbon atom bonded with any of X 5 ⁇ X 8, wherein the general formula (C), X Any of 5 to X 8 is a carbon atom bonded to a nitrogen atom in the 5-membered ring in the condensed ring containing X 9 to X 12 and X 13 to X 16.
  • any one of X 5 to X 8 is Y 1 to Y 8 is a carbon atom bonded to any one of Y 8
  • any one of X 5 to X 8 and X 18 is a carbon atom bonded to any one of Y 1 to Y 8
  • any of X 5 to X 8 and X 18 is a carbon atom bonded to any one of Y 1 to Y 8
  • any of X 5 to X 8 and X 18 is a carbon atom bonded to * m1
  • any of X 5 to X 8 and X 18 is a carbon atom bonded to * m2.
  • * m1 and * m2 are X 5 is a binding site with any of ⁇ X 8 and X 18, in the general formula (N), the one of X 5 ⁇ X 8, a carbon atom bonded to the * n1, of X 5 ⁇ X 8 Any of them is a carbon atom bonded to * n2, each of * n1 and * n2 is a bonding site to any of X 5 to X 8 , and each Rx is independently a hydrogen atom or a substituent; Rx as a substituent is each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, substituted Or an unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, a substituted or unsubstitute
  • Hydrogen group substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, substituted Or an unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted phosphoryl group, and a substituted or unsubstituted group.
  • an electronic apparatus including the organic electroluminescence element according to one aspect of the present invention.
  • an organic electroluminescent element that can improve luminous efficiency and color purity, and to provide an electronic device including the organic electroluminescent element.
  • the organic EL element according to this embodiment includes an organic layer between a pair of electrodes.
  • This organic layer is composed of at least one layer composed of an organic compound.
  • the 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 contain the layer to obtain.
  • the following configurations (a) to (e) can be given.
  • (A) Anode / light emitting layer / cathode (b) Anode / hole injection / transport layer / light emitting layer / cathode (c) Anode / light emitting layer / electron injection / transport layer / cathode (d) Anode / hole injection / transport Layer / light emitting layer / electron injection / transport layer / cathode (e) anode / hole injection / transport layer / light emitting layer / barrier layer / electron injection / transport layer / cathode
  • the configuration of (d) is preferably used. .
  • the “light emitting layer” is an organic layer having a light emitting function.
  • the “hole injection / transport layer” means “at least one of a hole injection layer and a hole transport layer”.
  • the “electron injection / transport layer” means “at least one of an electron injection layer and an electron transport layer”.
  • a hole injection layer is provided between the hole transport layer and the anode.
  • an organic EL element has an electron injection layer and an electron carrying layer, it is preferable that the electron injection layer is provided between the electron carrying layer and the cathode.
  • each of the hole injection layer, the hole transport layer, the electron transport layer, and the electron injection layer may be composed of a single layer or a plurality of layers.
  • FIG. 1 shows a schematic configuration of an example of the organic EL element according to this embodiment.
  • 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 hole injection layer 6, a hole transport layer 7, a light emitting layer 5, an electron transport layer 8, and an electron injection layer 9 that are stacked in this order from the anode 3 side.
  • the light emitting layer 5 of the organic EL device 1 includes a first compound and a second compound.
  • the light emitting layer 5 may contain a metal complex. It is preferable that the light emitting layer 5 does not contain a phosphorescent metal complex.
  • the first compound according to this embodiment is a delayed fluorescent compound.
  • the first compound according to this embodiment is represented by the following general formula (1).
  • X is an oxygen atom, a sulfur atom, or a selenium atom
  • Y 1 to Y 8 are each independently CR 1a (a carbon atom bonded to R 1a ), CR 1b (a carbon atom bonded to R 1b ), or a nitrogen atom; Provided that at least two of Y 1 to Y 8 are nitrogen atoms, and at least one of Y 1 to Y 8 is CR 1a , R 1a is independently is any group selected from the group consisting of groups represented by the following general formula (A) ⁇ (N), if R 1a there are a plurality, the plurality of R 1a is May be the same or different from each other,
  • Each R 1b is independently a hydrogen atom or a substituent;
  • R 1b as a substituent is each independently A halogen atom, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted cycloalkyl group having
  • X 1 to X 20 are each independently a nitrogen atom or CRx (a carbon atom bonded to Rx), However, Wherein
  • any one of X 5 to X 8 is a carbon atom bonded to a nitrogen atom in a 5-membered ring in a condensed ring containing X 9 to X 12 and X 13 to X 16 ;
  • formula (E) any of X 5 ⁇ X 8 and X 18, a carbon atom bonded with any of X 9 ⁇ X 12, any of X 9 ⁇ X 12, X 5 ⁇ X A carbon atom bonded to any of 8 and X 18 ;
  • formula (F) any of X 5 ⁇
  • any one of X 5 to X 8 and X 18 is a nitrogen atom linking a ring containing X 9 to X 12 and X 19 and a ring containing X 13 to X 16 and X 20 A carbon atom bonded to
  • any one of X 5 to X 8 is bonded to a nitrogen atom that connects a ring containing X 9 to X 12 and X 19 and a ring containing X 13 to X 16 and X 20.
  • any one of X 5 to X 8 is a carbon atom bonded to any one of Y 1 to Y 8 ;
  • any one of X 5 to X 8 and X 18 is a carbon atom bonded to any one of Y 1 to Y 8 ;
  • any of X 5 to X 8 and X 18 is a carbon atom bonded to * m1, and any of X 5 to X 8 and X 18 is a carbon bonded to * m2.
  • any of X 5 to X 8 is a carbon atom bonded to * n1
  • any of X 5 to X 8 is a carbon atom bonded to * n2
  • And * n2 are each a binding site to any of X 5 to X 8
  • Each Rx is independently a hydrogen atom or a substituent
  • Rx as a substituent is each independently A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atom
  • Ara is A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, Selected from the group consisting of a substituted or unsubstituted phosphoryl group and a substituted or unsubstituted silyl group; * Is a binding site with any of Y 1 to Y 8 .
  • X 1 to X 20 are preferably CRx.
  • Rx it is preferred that a plurality of Rx are directly bonded to form a saturated or unsaturated ring.
  • Rx When Rx is bonded to form a ring, it may be a condensed ring or a non-condensed ring. In the present embodiment, it is also preferable that Rx do not form a ring.
  • Examples of the groups represented by the general formulas (A) to (N) include the following groups.
  • S 1 to S 7 are each independently a hydrogen atom or a substituent
  • S 1 to S 7 as substituents are each independently A halogen atom
  • a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, A substituted or unsubstituted aralkyl group having 5 to 30 carbon atoms
  • a substituted or unsubstituted amino group A substituted or unsubstituted silyl group, A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, A substituted or unsubstituted
  • the wavy line portion represents a bonding site with any of Y 1 to Y 8 in the general formula (1).
  • At least one of Y 1 to Y 4 is preferably a nitrogen atom.
  • the first compound is preferably a compound represented by the following general formula (11).
  • Y 11 to Y 14 are each independently CR 1a , CR 1b , or a nitrogen atom
  • Y 15 to Y 18 are each independently CR 1b or a nitrogen atom
  • any one of Y 11 to Y 14 is CR 1a
  • at least two of Y 11 to Y 18 are nitrogen atoms
  • at least one of Y 11 to Y 14 is a nitrogen atom
  • X, R 1a and R 1b it is the X in the general formula (1), respectively and R 1a and R 1b, synonymous.
  • Examples of the compound represented by the general formula (11) include compounds represented by the following general formulas (11-1) to (11-4).
  • X, Y 11 ⁇ Y 18, and R 1a is X in the general formula (11), Y 11 ⁇ Y 18, and R 1a and are each synonymous.
  • Y 11 in the general formula (11) is a nitrogen atom
  • any one of Y 12 to Y 14 is CR 1a
  • the other Y 12 Y 14 is each independently CR 1a , CR 1b , or a nitrogen atom
  • Y 15 to Y 18 are each independently CR 1b or a nitrogen atom
  • at least one of Y 12 to Y 18 is nitrogen.
  • Examples of the compounds represented by the general formulas (11-1) to (11-4) include compounds represented by the following general formulas (11-a) to (11-p).
  • X, and Y 11 - Y 18 is X, and respectively Y 11 - Y 18 synonymous in the general formula (11-1) to (11-4), X 1 ⁇ X 8, X 17 , X 18, and Ara is, X 1 ⁇ X 8, X 17, X 18 in the general formula (A) ⁇ (N), and Ara and are each synonymous.
  • any of X 5 to X 8 is a carbon atom bonded to any of Y 11 to Y 14 ;
  • any of X 5 to X 8 and X 18 is a carbon atom bonded to any of Y 11 to Y 14 .
  • any of X 5 to X 8 and X 18 is a carbon atom bonded to Z.
  • n is 0 or 1;
  • Z is any group represented by the following general formulas (Z1) to (Z4).
  • any of X 9 to X 12 and X 19 is a carbon atom bonded to any of X 5 to X 8 and X 18 (the wavy line part is the And represents a bonding site with any of X 5 to X 8 and X 18 in the general formulas (11-a) to (11-h).
  • examples of the compound represented by the general formula (1) include compounds represented by the following general formulas (1-1) to (1-16).
  • R 1 to R 8 are each independently R 1a or R 1b , provided that at least one of R 1 to R 8 is R 1a , X, R 1a and R 1b, it is the X in the general formula (1), respectively and R 1a and R 1b, synonymous.
  • any two of Y 11 ⁇ Y 14 is a nitrogen atom, and more preferably either only two of Y 11 ⁇ Y 14 of Y 11 ⁇ Y 18 is a nitrogen atom .
  • the first compound has the following general formulas (11A-1) to (11A-3), (11B-1) to (11B-3), (11C-1) to (11C-3), And a compound represented by any one of (11D-1) to (11D-3).
  • the first compound is any one of the compounds represented by the general formulas (11A-1) to (11A-3) and the general formulas (11C-1) to (11C-3). It is preferably a compound represented by any one of the general formulas (11A-1) to (11A-3). In the present embodiment, the first compound is more preferably a compound represented by the following general formula (11Aa).
  • Y 112 and Y 115 to Y 118 are each independently CR 1b , X, R 1a and R 1b, it is the X in the general formula (1), respectively and R 1a and R 1b, synonymous.
  • R 1a is preferably any group selected from the group consisting of groups represented by the general formulas (A), (B), (C), and (G).
  • X is preferably an oxygen atom or a sulfur atom, and more preferably an oxygen atom.
  • R 1b is 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 ring atoms. It is preferably any group.
  • Rx is 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 ring atoms. Any group is preferred.
  • Ara is 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 ring atoms. Any group is preferred.
  • Delayed fluorescence (thermally activated delayed fluorescence) is explained on pages 261 to 268 of "Device properties of organic semiconductors" (edited by Chiya Adachi, published by Kodansha).
  • TADF thermally activated delayed fluorescence
  • FIG. 10.38 in this document explains the mechanism of delayed fluorescence generation.
  • the first compound 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 (Photo Luminescence) measurement.
  • Transient PL measurement is a method of measuring the decay behavior (transient characteristics) of PL emission after irradiating a sample with a pulse 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 gradually attenuated due to light emission from singlet excitons generated via a long-lived triplet exciton.
  • the emission intensity derived from delayed fluorescence can be obtained.
  • 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 irradiated with a pulse laser from the pulse laser unit 101 to excite the doping material.
  • Light emission is extracted in a direction of 90 degrees with respect to the irradiation direction of the excitation light, the extracted light is dispersed by the spectroscope 103, and a two-dimensional image is formed in the streak camera 104.
  • a two-dimensional image in which the vertical axis corresponds to time, the horizontal axis corresponds to wavelength, and the bright spot corresponds to emission intensity.
  • an emission spectrum in which the vertical axis represents the emission intensity and the horizontal axis represents the wavelength can be obtained.
  • an attenuation curve in which the vertical axis represents the logarithm of the emission intensity and the horizontal axis represents time can be obtained.
  • 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.
  • 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 of FIG.
  • the first compound is excited with pulsed light having a wavelength that is absorbed by the first compound (light irradiated from a pulse laser) and then promptly observed from the excited state. After the excitation, there is delay light emission (delayed light emission) that is not observed immediately but is observed thereafter.
  • the amount of delay light emission is preferably 5% or more with respect to the amount of Promp light emission (immediate light emission). That is, the amount of Prompt luminescence (immediate emission) and X P, the amount of Delay emission (delayed luminescence) is taken as X D, it is preferred values for X D / X P is 0.05 or more.
  • 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 described in the said literature.
  • a sample used for measurement of delayed fluorescence for example, a first compound and the following compound TH-2 are co-deposited on a quartz substrate so that the ratio of the first compound is 12% by mass.
  • a sample in which a thin film having a thickness of 100 nm is formed can be used.
  • the second compound according to this embodiment is a fluorescent compound.
  • the second compound of this embodiment is not particularly limited as long as it is a fluorescent compound.
  • the second compound preferably exhibits fluorescence with a main peak wavelength of 550 nm or less.
  • a 2nd compound shows the fluorescence emission whose main peak wavelength is 430 nm or more.
  • the second compound preferably exhibits fluorescence emission having a main peak wavelength of 430 nm or more and 550 nm or less.
  • the second compound also preferably exhibits fluorescence emission having a main peak wavelength of 430 nm to 500 nm.
  • the second compound also preferably exhibits fluorescence emission having a main peak wavelength of 500 nm to 550 nm.
  • the second compound also preferably exhibits fluorescence emission having a main peak wavelength of 550 nm to 750 nm.
  • 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 second compound is dissolved at a concentration of 10 ⁇ 6 mol / liter to 10 ⁇ 5 mol / liter. Refers to the peak wavelength.
  • the second compound preferably exhibits blue fluorescence. According to the organic EL element of this embodiment, blue light emission efficiency can be improved.
  • the second compound also preferably exhibits red fluorescence.
  • the red light emission efficiency can also be improved.
  • the second compound also preferably exhibits green fluorescence. According to the organic EL element of this embodiment, the green light emission efficiency can also be improved.
  • the second compound is preferably a material having a high emission quantum yield.
  • the second compound is preferably a compound represented by the following general formula (20).
  • R 21 and R 22 are each independently a hydrogen atom or a substituent, R 21 and R 22 as substituents are each independently A halogen atom, A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, A substituted or unsubstituted phosphoryl group, A substituted or unsubstituted silyl group, A cyano group, Selected from the group consisting of a nitro group and a substituted or unsubstituted aromatic hydrocarbon group
  • a ring formed by combining R 21 and R 22 as a substituent and a ring formed by combining a plurality of R 23 as a substituent is a 5-membered ring, a 6-membered ring, or a 7-membered ring.
  • the ring may be an aliphatic ring, an aromatic ring, or a heterocyclic ring, and may further have a substituent, and the plurality of rings may be the same or different from each other. May be.
  • X 21 to X 28 are preferably each independently a carbon atom bonded to R 23 .
  • the second compound is represented by the following general formula (20A).
  • R 231 to R 238 are independently the same as R 23 described above, and R 21 and R 22 are the same as R 21 and R 22 described above.
  • any one of R 231 to R 234 is a substituent, and the substituents are bonded to each other to form a ring, or any of R 235 to R 238 is a substituent. And it is preferable that the substituents are bonded to each other to form a ring.
  • any one of R 231 to R 234 is bonded to form a ring, and any one of R 235 to R 238 is bonded to form a ring. It is also preferable to form.
  • the ring formed by bonding of these substituents is preferably an aromatic 6-membered ring. This aromatic 6-membered ring may further have a substituent.
  • the second compound is also preferably a compound represented by the following general formula (20B).
  • R 233 to R 236 and R 241 to R 248 are each independently synonymous with R 23 described above, and R 21 and R 22 are the same as R 21 and R 22 described above. It is synonymous.
  • R 241 , R 242 , R 244 , R 245 , R 247 and R 248 are preferably hydrogen atoms, and R 243 and R 246 are preferably substituents.
  • R 243 and R 246 as substituents are each independently A halogen atom, A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, A substituted or unsubstituted phosphoryl group, A substituted or unsubstituted silyl group, A cyano group, It is selected from the group consisting of a nitro group and a substituted or unsubstituted carboxy group.
  • R 243 and R 246 as substituents are a group consisting of a halogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms. Is preferably a group selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.
  • R 21 and R 22 each independently represent a halogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted carbon group having 1 to 30 carbon atoms. It is preferably any group selected from the group consisting of alkyl groups, more preferably a halogen atom, and even more preferably a fluorine atom.
  • the second compound is also preferably a compound represented by the following general formula (21).
  • n1 is an integer greater than or equal to 1
  • Ar 0 is a substituted or unsubstituted condensed aromatic hydrocarbon group having 10 to 40 ring carbon atoms
  • Ar 1 and Ar 2 are each independently A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, Selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms; Ar 1 and Ar 2 may combine to form a saturated or unsaturated ring.
  • the plurality of Ar 1 may be the same or different from each other, and the plurality of Ar 2 are May be the same or different from each other, L 0 is a single bond or a linking group, and when L 0 is a linking group, the linking group is When n1 is 2 or more, 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 ring atoms, The plurality of L 0 may be the same as or different from each other.
  • Ar 0 in the general formula (21) is preferably a group having a benzofluorene skeleton, a fluoranthene skeleton, a pyrene skeleton, or a chrysene skeleton.
  • a group having a chrysene skeleton is more preferable.
  • n1 in the general formula (21) is 2, it is also preferred L 0 are both a single bond.
  • the nitrogen atom in the general formula (21) is preferably bonded to the 1-position and the 6-position of the pyrene skeleton
  • the nitrogen atom in the general formula (21) is preferably bonded to the 6th and 12th positions of the chrysene skeleton.
  • Ar 0 in the general formula (21) is also preferably a group having a benzofluorene skeleton, and the group having a benzofluorene skeleton as the Ar 0 is represented by the following general formula (Ar-1) It is preferable that it is group represented by these.
  • R 111 and R 112 are each independently a hydrogen atom or a substituent, R 111 and R 112 as substituents are each independently Selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms; R 113 to R 122 are each independently a hydrogen atom, a substituent, or a single bond bonded to L 0 , provided that at least one of R 113 to R 122 is a single bond bonded to L 0 .
  • R 113 to R 122 as substituents are each independently A halogen atom, A cyano group, Nitro group, Hydroxyl group, A substituted or unsubstituted silyl group, A substituted or unsubstituted carboxy group, A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, A substituted or unsubstituted arylamino group having 6 to 30 ring carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted arylalkoxy group having 6 to 30 ring carbon atoms, Selected from the group consisting of a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms and a
  • the group represented by the general formula (Ar-1) is preferably a group represented by the following general formula (Ar-2).
  • R 111 , R 112 , R A , and R B are each independently a hydrogen atom or a substituent
  • R 111 , R 112 , R A and R B as substituents are each independently Selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms
  • R 113 and R 116 to R 126 are each independently a hydrogen atom, a substituent, or a single bond bonded to L 0 , provided that at least one of R 113 , R 116 to R 126 is L 0
  • a single bond that binds to R 113 and R 116 to R 126 as substituents are each independently A halogen atom, A cyano group, Nitro group, Hydroxyl group, A substituted or unsubstituted silyl group, A substituted or unsubstituted carboxy group
  • At least one of R 121 and R 125 is a single bond bonded to L 0 .
  • R 111 , R 112 , R A , and R B are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and a substituted or unsubstituted ring forming carbon number of 6 to 30 It is preferably any group selected from the group consisting of:
  • Ar 1 and Ar 2 in the general formula (21) are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted ring. It is preferably any group selected from the group consisting of heterocyclic groups having 5 to 30 atoms, and at least one of Ar 1 and Ar 2 is a substituted or unsubstituted ring carbon having 6 to 30 carbon atoms. More preferably, it is any group selected from the group consisting of aromatic hydrocarbon groups.
  • Ar 1 and Ar 2 in the general formula (21) are a group represented by the following general formula (21a).
  • Ar 0 in the general formula (21) is preferably a group having a pyrene skeleton or a chrysene skeleton.
  • x is an integer from 0 to 3
  • y is an integer from 0 to 7
  • X 5a is an oxygen atom, a sulfur atom, or a selenium atom
  • x is 0, the group represented by the general formula (21a) and the nitrogen atom in the general formula (21) are bonded by a single bond
  • x is an integer of 1 to 3
  • Ar 5 is a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.
  • a plurality of Ar 5 may be the same as each other They may be different, Ar 5 may be bonded to each other to form a saturated or unsaturated ring,
  • Each R 5 is independently A halogen atom, A cyano group, Nitro group, Hydroxyl group, A substituted or unsubstituted silyl group, A substituted or unsubstituted carboxy group, A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, A substituted or unsubstituted arylamino group having 6 to 30 ring carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, A substituted or unsubstituted arylalkoxy group having 6 to 30 ring carbon atoms, S
  • X 5a in the general formula (21a) is preferably an oxygen atom or a sulfur atom, and more preferably an oxygen atom.
  • Ar 1 in the general formula (21) is any group selected from the group consisting of substituted or unsubstituted aromatic hydrocarbon groups having 6 to 30 ring carbon atoms. It is preferably a group selected from the group consisting of substituted or unsubstituted aromatic hydrocarbon groups having 6 to 20 ring carbon atoms, and includes a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, More preferably, it is any group selected from the group consisting of a terphenyl group and a fluorenyl group.
  • Ar 2 in the general formula (21) is preferably a group represented by the general formula (21a).
  • At least one of Ar 1 and Ar 2 in the general formula (21) is preferably a group represented by the general formula (Ar-1), and the general formula (Ar-2) It is more preferable that it is group represented by.
  • Ar 0 in the general formula (21) is preferably a group having a benzofluorene skeleton.
  • n1 in the general formula (21) is preferably 1 or 2.
  • the second compound is also preferably a compound represented by the following general formula (22).
  • p is an integer from 0 to 5
  • q and r are each independently an integer of 1 to 5
  • Ar 10 is a substituted or unsubstituted condensed aromatic hydrocarbon group having 10 to 40 ring carbon atoms
  • R 10 is A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, Selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms; when q is 2 or more, the plurality of R 10 may be the same as or different from each other, and R 10 may be bonded to each other to form a saturated or unsaturated ring; When p is 0, Ar 10 and R 10 are bonded by a single bond, When p is an integer from 1 to 5, L 10 is A linking group
  • binding mode of the compound represented by the general formula (22) examples include, for example, the binding modes shown in Table 1 below.
  • Ar 10 in the general formula (22) is preferably a group having a benzofluorene skeleton, a fluoranthene skeleton, a pyrene skeleton, or a chrysene skeleton, and more preferably a group having a fluoranthene skeleton. And more preferably a group having a fluoranthene skeleton (benzofluoranthene skeleton) condensed with a benzene ring.
  • a 2nd compound can be manufactured by the method as described in international publication 2008/059713, international publication 2010/122810, etc., for example.
  • ⁇ TADF mechanism> In the organic EL device of this embodiment, it is preferable to use a compound having a small ⁇ ST (M1) as the first compound.
  • ⁇ ST (M1) When ⁇ ST (M1) is small, reverse intersystem crossing from the triplet level of the first compound to the singlet level of the first compound is likely to occur due to externally applied thermal energy.
  • An energy state conversion mechanism in which the excited triplet state of the electrically excited exciton inside the organic EL element is spin-exchanged to the excited singlet state by crossing between inverse terms is called a TADF mechanism.
  • FIG. 4 is a diagram illustrating an example of the relationship between the energy level and the energy transfer of the first compound and the second compound in the light emitting layer.
  • S0 represents the ground state
  • S1 (M1) represents the lowest excited singlet state of the first compound
  • T1 (M1) represents the lowest excited triplet state of the first compound
  • S1 (M2) represents the lowest excited singlet state of the second compound
  • T1 (M2) represents the lowest excited triplet state of the second compound.
  • the dashed arrow from S1 (M1) to S1 (M2) in FIG. 4 represents the Forster energy transfer from the lowest excited singlet state of the first compound to the lowest excited singlet state of the second compound.
  • the lowest excited triplet state T1 (M1) is reversed to the lowest excited singlet state S1 (M1) by thermal energy. Intersection is possible.
  • the energy gap T 77K (M1) at 77 [K] of the first compound is preferably larger than the energy gap T 77K (M2) at 77 [K] of the second compound.
  • the measurement of the energy gap T 77K at 77 [K] is performed as follows.
  • a sample is used.
  • 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 energy amount calculated from the following conversion formula 1 is defined as an energy gap T 77K at 77 [K].
  • Conversion formula 1: T 77K [eV] 1239.85 / ⁇ edge
  • an F-4500 type spectrofluorometer main body manufactured by Hitachi High-Technology Co., Ltd. can be used. Note that the phosphorescence measuring apparatus is not limited to this.
  • the tangent to the rising edge on the short wavelength side of the phosphorescence spectrum is drawn as follows.
  • 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 wavelength range of light emitted by the organic EL element 1 of the present embodiment is preferably 430 nm or more and 550 nm or less. That is, it is preferable that the main peak wavelength of the light emitted from the organic EL element 1 is included in the range of 430 nm to 550 nm when the organic EL element 1 of the present embodiment emits light.
  • the wavelength range of light emitted by the organic EL element 1 of the present embodiment is preferably 430 nm or more and 500 nm or less.
  • the wavelength range of light emitted by the organic EL element 1 of the present embodiment is preferably 500 nm or more and 550 nm or less.
  • the wavelength range of light emitted by the organic EL element 1 of the present embodiment is preferably 550 nm or more and 750 nm or less.
  • the organic EL element 1 of the present embodiment When the organic EL element 1 of the present embodiment is caused to emit light, it is preferable that mainly the second compound emits light in the light emitting layer 5.
  • the content rate of a 2nd compound in the light emitting layer 5 is 10 mass% or less, and is 5 mass% or less. Is more preferable, and more preferably 0.01% by mass or more and 1% by mass or less.
  • the film thickness of the light emitting layer 5 in the organic EL element 1 of this embodiment becomes like this.
  • they are 5 nm or more and 50 nm or less, More preferably, they are 7 nm or more and 50 nm or less, More preferably, they are 10 nm or more and 50 nm or less. If the thickness is 5 nm or more, the light emitting layer 5 can be easily formed and the chromaticity can be easily adjusted. Moreover, if it is 50 nm or less, the raise of a drive voltage can be suppressed.
  • the substrate 2 is used as a support for the organic EL element 1.
  • the substrate 2 for example, glass, quartz, plastic, or the like can be used.
  • a flexible substrate may be used.
  • the flexible substrate is a substrate that can be bent (flexible), and examples thereof include a plastic substrate.
  • the material forming the plastic substrate include polycarbonate, polyarylate, polyether sulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate.
  • an inorganic vapor deposition film can also be used.
  • anode For the anode 3 formed on the substrate 2, 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, indium oxide containing tungsten oxide and zinc oxide, And graphene.
  • ITO indium tin oxide
  • ITO indium oxide-tin oxide containing silicon or silicon oxide
  • indium oxide-zinc oxide indium oxide containing tungsten oxide and zinc oxide
  • graphene graphene.
  • These materials are usually formed by sputtering.
  • indium oxide-zinc oxide can be formed by a sputtering method by using a target in which 1% by mass to 10% by mass of zinc oxide is added to indium oxide.
  • indium oxide containing tungsten oxide and zinc oxide is a target containing 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.
  • the hole injection layer 6 formed in contact with the anode 3 is made of a composite material that facilitates hole injection regardless of the work function of the anode 3. It is formed.
  • Electrode materials for example, metals, alloys, electrically conductive compounds, and mixtures thereof, and other elements belonging to Group 1 or Group 2 of the periodic table
  • An element belonging to Group 1 of the Periodic Table of Elements, an element belonging to Group 2 of the Periodic Table of Elements, a rare earth metal, an alloy containing these, and the like, which are materials having a low work function, can also be used as anode 3.
  • Examples of the element belonging to Group 1 of the periodic table include alkali metals.
  • the elements belonging to Group 2 of the periodic table include alkaline earth metals.
  • the alkali metal include lithium (Li) and cesium (Cs).
  • alkaline earth metal examples include magnesium (Mg), calcium (Ca), strontium (Sr), and the like.
  • rare earth metals include europium (Eu) and ytterbium (Yb).
  • alloys containing these metals include MgAg and AlLi.
  • a vacuum evaporation method, a sputtering method, etc. can be used.
  • coating method, an inkjet method, etc. can be used.
  • the hole injection layer 6 is a layer containing a substance having a high hole injection property.
  • substances having a high hole injection property include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, and silver oxide.
  • An oxide, tungsten oxide, manganese oxide, or the like can be used.
  • TDATA N-diphenylamino triphenylamine
  • MTDATA 4,4 ′, 4 ′′ -tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine
  • DPAB 4,4′-bis [N- (4-diphenylaminophenyl) -N -Phenylamino] biphenyl
  • DNTPD 1,3,5-tris [N- (4-diphenylaminophenyl) -N-phenylamino] benzen
  • a high molecular compound can also be used.
  • the polymer compound include oligomers, dendrimers, and polymers.
  • poly (N-vinylcarbazole) abbreviation: PVK
  • poly (4-vinyltriphenylamine) abbreviation: PVTPA
  • 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 ]
  • Poly-TPD Poly-TPD
  • a polymer compound to which an acid such as poly (3,4-ethylenedioxythiophene) / poly (styrenesulfonic acid) (PEDOT / PSS) and polyaniline / poly (styrenesulfonic acid) (PAni / PSS) is added can also be used.
  • the hole transport layer 7 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.
  • NPB 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl
  • NPB N, N′-bis (3-methylphenyl) -N, N′— Diphenyl- [1,1′-biphenyl] -4,4′-diamine
  • BAFLP 4-phenyl-4 ′-(9-phenylfluoren-9-yl) triphenylamine
  • BAFLP 4-phenyl-4 ′-bis [N- (9,9-dimethylfluoren-2-yl) -N-phenylamino] biphenyl
  • DFLDPBi 4,4 ′, 4 ′′ -tris (N, N-diphenylamino)
  • TDATA 4,4 ′, 4 ′′ -tris [N- (3-methylphenyl) -N-phenyla
  • the substances mentioned here are mainly substances having a hole mobility of 10 ⁇ 6 cm 2 / (V ⁇ s) or more.
  • the hole transport layer 7 includes CBP, 9- [4- (N-carbazolyl)] phenyl-10-phenylanthracene (CzPA), and 9-phenyl-3- [4- (10-phenyl-9-anthryl).
  • a carbazole derivative such as phenyl] -9H-carbazole (PCzPA), an anthracene derivative such as t-BuDNA, DNA, and DPAnth may be used.
  • Polymer compounds such as poly (N-vinylcarbazole) (abbreviation: PVK) and poly (4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.
  • PVK poly (N-vinylcarbazole)
  • PVTPA poly (4-vinyltriphenylamine)
  • any substance other than these may be used as long as it has a property of transporting more holes than electrons.
  • the layer containing a substance having a high hole-transport property is not limited to a single layer, and may be a layer in which two or more layers containing the above substances are stacked. When two or more hole transport layers are arranged, it is preferable to arrange a layer containing a material having a larger energy gap on the side closer to the light emitting layer 5.
  • the hole transport layer 7 prevents the triplet excitons generated in the light emitting layer 5 from diffusing into the hole transport layer 7 and the hole injection layer 6, and converts the triplet excitons into the light emitting layer 5. It preferably has a function of confining inside.
  • the electron transport layer 8 is a layer containing a substance having a high electron transport property.
  • the electron transport layer 8 includes 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes; 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives; and 3 ) High molecular compounds can be used.
  • Alq tris (4-methyl-8-quinolinolato) aluminum (abbreviation: Almq 3 ), bis (10-hydroxybenzo [h] quinolinato) beryllium (abbreviation: BeBq 2 ), Metal complexes such as BAlq, Znq, ZnPBO, and ZnBTZ 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.
  • a substance other than the above may be used as the electron transport layer 8 as long as the substance has a higher electron transport property than the hole transport property.
  • the electron transport layer 8 is not limited to a single layer, and may be a layer in which two or more layers made of the above substances are stacked.
  • a polymer compound can be used for the electron transport layer 8.
  • 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) or the like can be used.
  • the electron transport layer 8 prevents the triplet excitons generated in the light emitting layer 5 from diffusing into the electron transport layer 8 and the electron injection layer 9 and confines the triplet excitons in the light emitting layer 5. It preferably has a function.
  • the electron injection layer 9 is a layer containing a substance having a high electron injection property.
  • the electron injection layer 9 includes lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), and lithium oxide (LiOx).
  • Alkali metals, alkaline earth metals, or compounds 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 4 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 9.
  • 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, etc.) constituting the electron transport layer 8 described above is used.
  • the electron donor may be any substance that exhibits an electron donating property to the organic compound.
  • an alkali metal, an alkaline earth metal, or a rare earth metal is preferable, and examples thereof include lithium, cesium, magnesium, calcium, erbium, and ytterbium.
  • an alkali metal oxide or an alkaline earth metal oxide as an electron donor, and examples thereof include lithium oxide, calcium oxide, and barium oxide.
  • a Lewis base such as magnesium oxide can also be used.
  • an organic compound such as tetrathiafulvalene (abbreviation: TTF) can be used.
  • cathode For the cathode 4, 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).
  • a cathode material include elements belonging to Group 1 of the periodic table, elements belonging to Group 2 of the periodic table, rare earth metals, and alloys containing these.
  • the element belonging to Group 1 of the periodic table include alkali metals.
  • the elements belonging to Group 2 of the periodic table include alkaline earth metals. Examples of the alkali metal include lithium (Li) and cesium (Cs). Examples of the alkaline earth metal include magnesium (Mg), calcium (Ca), and strontium (Sr).
  • Examples of rare earth metals include europium (Eu) and ytterbium (Yb).
  • Examples of alloys containing these metals include MgAg and AlLi.
  • a vacuum evaporation method, a sputtering method, etc. can be used.
  • a silver paste etc. the apply
  • various conductive materials such as Al, Ag, ITO, graphene, and indium oxide-tin oxide containing silicon or silicon oxide can be used regardless of the work function.
  • the cathode 4 can be formed. These conductive materials can be formed by a sputtering method, an inkjet method, a spin coating method, or the like.
  • the method for forming each layer of the organic EL element 1 of the present embodiment is not limited to those described above, and known methods such as a dry film forming method and a wet film forming method can be employed.
  • the dry film forming method include a vacuum deposition method, a sputtering method, a plasma method, and an ion plating method.
  • the wet film forming method include a spin coating method, a dipping method, a flow coating method, and an ink jet method.
  • the film thickness of each organic layer of the organic EL element 1 of the present embodiment is not limited except as specifically mentioned above.
  • the film thickness is preferably in the range of several nm to 1 ⁇ m in order to prevent defects such as pinholes from occurring and to prevent deterioration in efficiency due to the need for a high applied voltage.
  • 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 carbon number of the fluorene ring as a substituent 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 heterocycle) having a structure in which atoms are bonded in a cyclic manner (for example, a monocyclic ring, a condensed ring, or a ring assembly) Of the ring compound) represents the number of atoms constituting the ring itself.
  • 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 are 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.
  • the hydrogen atom bonded to the carbon atom of the pyridine ring or the quinazoline ring and the atoms constituting the substituent are 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 include a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, and a phenanthryl group.
  • the aryl group preferably has 6 to 20 ring carbon atoms, more preferably 6 to 14, and still more preferably 6 to 12.
  • aryl groups a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a terphenyl group, and a fluorenyl group are even more preferable.
  • 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group and 4-fluorenyl group a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms in the present specification, which will be described later, on the 9-position carbon atom, or It is preferable that the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms is substituted.
  • a heterocyclic group having 5 to 30 ring-forming atoms includes nitrogen, sulfur, oxygen as a heteroatom.
  • it contains at least one atom selected from the group consisting of silicon, selenium atom, and germanium atom, and more preferably contains at least one atom selected from the group consisting of nitrogen, sulfur, and oxygen preferable.
  • heterocyclic group having 5 to 30 ring atoms in the present specification examples include, for example, pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolyl group, isoquinolinyl group, naphthyridinyl group, phthalazinyl group, quinoxalinyl group, Quinazolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group, indolyl group, benzimidazolyl group, indazolyl group, imidazolpyridinyl group, benz Triazolyl, carbazolyl, furyl, thienyl, oxazolyl, thiazolyl, isoxazolyl, is
  • the number of ring-forming atoms of the heterocyclic group is preferably 5 to 20, and more preferably 5 to 14.
  • 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.
  • Xa 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 include a group further condensed with a carbazole ring as represented by the following formula, for example. 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 preferably has 1 to 10 carbon atoms, and more preferably 1 to 6 carbon atoms.
  • methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group Even more preferred are amyl, isoamyl, and neopentyl groups.
  • Examples of the cycloalkyl group having 3 to 30 carbon atoms in the present specification 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 even more preferable.
  • halogenated alkyl group in which the alkyl group is substituted with a halogen atom examples include groups in which the alkyl group having 1 to 30 carbon atoms is substituted with one or more halogen atoms. 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.
  • Examples of the substituted silyl group in the present specification include an alkylsilyl group having 3 to 30 carbon atoms and an arylsilyl group having 6 to 30 ring carbon atoms.
  • Examples of the alkylsilyl group having 3 to 30 carbon atoms in the present specification 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 as or different from each other.
  • Examples of the arylsilyl group having 6 to 30 ring carbon atoms in the present specification 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.
  • an alkoxy group having 1 to 30 carbon atoms is represented as —OZ 1 .
  • Z 1 include the above alkyl groups having 1 to 30 carbon atoms.
  • 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 a group in which the alkoxy group having 1 to 30 carbon atoms is substituted with one or more fluorine atoms.
  • the aryl group in the arylalkoxy group may be an aromatic hydrocarbon group or a heterocyclic group.
  • an arylalkoxy group having 5 to 30 carbon atoms is represented by —OZ 2 .
  • Z 2 include, for example, the above aryl group having 6 to 30 ring carbon atoms.
  • the number of carbon atoms forming the arylalkoxy group is preferably 6-20.
  • the arylalkoxy group include a phenoxy group.
  • the substituted amino group in this specification is represented as —NHR V or —N (R V ) 2 .
  • RV include the alkyl group having 1 to 30 carbon atoms and the aryl group having 6 to 30 ring carbon atoms.
  • the aryl group in the aralkyl group may be an aromatic hydrocarbon group or a heterocyclic group.
  • the aralkyl group having 5 to 30 carbon atoms is preferably an aralkyl group having 6 to 30 ring carbon atoms, and 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-mentioned aryl groups 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). 20, more preferably 1 to 10, and still more preferably 1 to 6).
  • the aralkyl group 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, 2- ⁇ -naphthylisopropyl group, and the like.
  • the alkenyl group having 2 to 30 carbon atoms may be either a straight chain or a branched chain, and examples thereof include a vinyl group, a propenyl group, a butenyl group, an oleyl group, an eicosapentaenyl group, and docosahexahexane.
  • examples include an enyl group, a styryl group, a 2,2-diphenylvinyl group, a 1,2,2-triphenylvinyl group, and a 2-phenyl-2-propenyl group.
  • Examples of the C3-C30 cycloalkenyl group in the present specification include a cyclopentadienyl group, a cyclopentenyl group, a cyclohexenyl group, and a cyclohexadienyl group.
  • the alkynyl group having 2 to 30 carbon atoms may be linear or branched, and examples thereof include ethynyl, propynyl, 2-phenylethynyl and the like.
  • Examples of the C3-C30 cycloalkynyl group in the present specification include a cyclopentynyl group and a cyclohexynyl group.
  • the substituted phosphoryl group in this specification is represented by the following general formula (P).
  • Ar P1 and Ar P2 are each independently a substituent selected from the group consisting of an alkyl group having 1 to 30 carbon atoms and an aryl group having 6 to 30 ring carbon atoms. Are more preferably selected from the group consisting of an alkyl group having 1 to 10 carbon atoms and an aryl group having 6 to 20 ring carbon atoms. It is more preferably any group selected from the group consisting of an alkyl group having 1 to 6 carbon atoms and an aryl group having 6 to 14 ring carbon atoms.
  • Examples of the substituted sulfanyl group in the present specification include a methylsulfanyl group, a phenylsulfanyl group, a diphenylsulfanyl group, a naphthylsulfanyl group, and a triphenylsulfanyl group.
  • Examples of the substituted sulfinyl group in the present specification include a methylsulfinyl group, a phenylsulfinyl group, a diphenylsulfinyl group, a naphthylsulfinyl group, and a triphenylsulfinyl group.
  • Examples of the substituted sulfonyl group in the present specification include a methylsulfonyl group, a phenylsulfonyl group, a diphenylsulfonyl group, a naphthylsulfonyl group, and a triphenylsulfonyl group.
  • Examples of the substituted phosphanyl group in the present specification include a phenylphosphanyl group.
  • Examples of the substituted carbonyl group in the present specification include a methylcarbonyl group, a phenylcarbonyl group, a diphenylcarbonyl group, a naphthylcarbonyl group, and a triphenylcarbonyl group.
  • the alkoxycarbonyl group having 2 to 30 carbon atoms is represented as —COOY ′.
  • Examples of this Y ′ include the above alkyl groups.
  • Examples of the substituted carboxy group in the present specification include a benzoyloxy group.
  • the arylthio group in this specification is represented as —SR V.
  • RV include the alkyl group having 1 to 30 carbon atoms and the aryl group having 6 to 30 ring carbon atoms.
  • the alkylthio group preferably has 1 to 20 carbon atoms, and the arylthio group preferably has 6 to 20 ring carbon atoms.
  • examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a fluorine atom is preferable.
  • 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 neutron numbers, that is, light hydrogen (Protium), deuterium (Deuterium), and tritium (Tritium).
  • substituents include an aryl group, a heterocyclic group, an alkyl group (a linear or branched alkyl group, a cycloalkyl group, a haloalkyl group), an alkylsilyl group as described above.
  • arylsilyl group alkoxy group, aryloxy group, alkylamino group, arylamino group, alkylthio group, arylthio group, aralkyl group, alkenyl group (straight chain or branched chain alkenyl group, cycloalkenyl group), alkynyl group ( In addition to a halogen atom, a cyano group, a hydroxyl group, a nitro group, and a carboxy group may be mentioned in addition to a linear or branched alkynyl group or cycloalkynyl group.
  • 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.
  • substituents include the above aryl group, heterocyclic group, alkyl group, alkylsilyl group, arylsilyl group, alkoxy group, aryloxy group, alkylamino group, arylamino group, alkylthio group, arylthio group, It may be further substituted with 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. A plurality of these substituents may be bonded to each other to form a ring.
  • unsubstituted in the case of “substituted or unsubstituted” means that a hydrogen atom is bonded without being substituted with the substituent.
  • carbon number XX to YY in the expression “substituted or unsubstituted ZZ group having XX to YY carbon atoms” represents the number of carbon atoms in the case where the ZZ group is unsubstituted and substituted. In this case, the number of carbon atoms in the substituent 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 and substituted. The number of atoms of the substituent in the case 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.
  • the ring structure is a saturated ring, an unsaturated ring, an aromatic hydrocarbon ring, or a heterocyclic ring.
  • examples of the aryl group in the linking group include a divalent or higher group obtained by removing one or more atoms from the monovalent group described above.
  • the light emitting layer contains the compound according to the present embodiment (first compound) and the fluorescent second compound, so that the light emission efficiency is improved. Can do. As described above, reverse intersystem crossing is likely to occur in the first compound contained in the light-emitting layer, and as a result, singlet excitation energy transfer from the first compound to the second compound is increased, and the first fluorescent emission property is increased. Since the two compounds emit light efficiently, it is presumed that the light emission efficiency and the emission color purity are improved. According to the organic EL device according to this embodiment, for example, when a blue fluorescent compound is used as the second compound, the emission color purity in the blue light emitting region of the organic EL device can be improved. .
  • the organic EL element 1 can be used for electronic devices such as 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 organic EL device according to the second embodiment is different from the organic EL device according to the first embodiment in that the light emitting layer further contains a third compound. Other points are the same as in the first embodiment.
  • the singlet energy of the third compound is greater than the singlet energy of the first compound.
  • a highly efficient organic EL element can be provided.
  • the organic EL device of the second embodiment includes a first compound having delayed fluorescence, a second compound having fluorescence, and a third compound having a singlet energy larger than that of the first compound in the light emitting layer. And the luminous efficiency is improved. The reason why the luminous efficiency is improved is considered to be that the carrier balance of the light emitting layer is improved by including the third compound.
  • FIG. 5 is a diagram illustrating an example of the relationship between the energy level and the energy transfer of the first compound, the second compound, and the third compound in the light emitting layer.
  • S0 represents a ground state.
  • S1 (M1) represents the lowest excited singlet state of the first compound
  • T1 (M1) represents the lowest excited triplet state of the first compound.
  • S1 (M2) represents the lowest excited singlet state of the second compound
  • T1 (M2) represents the lowest excited triplet state of the second compound.
  • S1 (M3) represents the lowest excited singlet state of the third compound
  • T1 (M3) represents the lowest excited triplet state of the third compound.
  • Examples of the absorption spectrum measuring device include, but are not limited to, a spectrophotometer (device name: U3310) manufactured by Hitachi.
  • the tangent to the falling edge on the long wavelength side of the absorption spectrum is drawn as follows. When moving on the spectrum curve in the long wavelength direction from the maximum value on the longest wavelength side among the maximum values of the absorption spectrum, 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 (except when the absorbance is 0.1 or less) is taken as the tangent to the fall on the long wavelength side of the absorption spectrum. In addition, the maximum point whose absorbance value is 0.2 or less is not included in the maximum value on the longest wavelength side.
  • the content rate of a 1st compound is 10 to 80 mass% in a light emitting layer, and the content rate of a 2nd compound is 1
  • the content is preferably 10% by mass or more and 10% by mass or less
  • the content of the third compound is preferably 10% by mass or more and 80% by mass or less.
  • the content ratio of the first compound is more preferably 20% by mass or more and 80% by mass or less, and further preferably 20% by mass or more and 60% by mass or less.
  • the upper limit of the total content of the first compound, the second compound, and the third compound in the light emitting layer is 100% by mass.
  • this embodiment does not exclude that materials other than a 1st compound, a 2nd compound, and a 3rd compound are contained in a light emitting layer.
  • the third compound is not particularly limited, but is preferably a compound other than an amine compound.
  • a carbazole derivative, a dibenzofuran derivative, and a dibenzothiophene derivative can be used as the third compound, but the third compound is not limited to these derivatives.
  • the third compound is also preferably a compound containing 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.
  • Y 31 to Y 36 are each independently a nitrogen atom or a carbon atom bonded to another atom in the molecule of the third compound; Provided that at least one of Y 31 to Y 36 is a carbon atom bonded to another atom in the molecule of the third compound;
  • Y 41 to Y 48 are each independently a nitrogen atom or a carbon atom bonded to another atom in the molecule of the third compound; Provided that at least one of Y 41 to Y 48 is a carbon atom bonded to another atom in the molecule of the third compound;
  • X 30 is a nitrogen atom bonded to another atom in the molecule of the third compound, or an oxygen atom or a sulfur atom.
  • the partial structure represented by the general formula (32) includes partial structures represented by the following general formulas (321), (322), (323), (324), (325), and (326). It is preferably any partial structure selected from the group.
  • X 30 is each independently a nitrogen atom bonded to another atom in the molecule of the third compound, an oxygen atom, or a sulfur atom
  • Y 41 to Y 48 are each independently a nitrogen atom or a carbon atom bonded to another atom in the molecule of the third compound
  • X 31 is independently a nitrogen atom, an oxygen atom, a sulfur atom, or a carbon atom that is bonded to another atom in the molecule of the third compound, which is bonded to another atom in the molecule of the third compound.
  • Y 51 to Y 54 each independently represent a nitrogen atom or a carbon atom bonded to another atom in the molecule of the third compound.
  • the third compound preferably has a partial structure represented by the general formula (323) among the general formulas (321) to (326).
  • the partial structure represented by the general formula (31) is at least one group selected from the group consisting of a group represented by the following general formula (33) and a group represented by the following general formula (34). It is preferably contained in the third compound.
  • the bonding positions being located at the meta positions can keep the energy gap T 77K (M3) at 77 [K] high. Therefore, it is preferable as the third compound.
  • Y 31 , Y 32 , Y 34 , and Y 36 are each independently a nitrogen atom or CR 31 ;
  • R 31 is a hydrogen atom or a substituent,
  • R 31 as a substituent is each independently A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, A substituted or unsubstituted silyl group, Substituted germanium groups, Substituted phosphine oxide groups
  • the substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms in R 31 is preferably a non-condensed ring.
  • a wavy line portion represents a bonding point with another atom or another structure in the molecule of the third compound.
  • Y 31 , Y 32 , Y 34 and Y 36 are preferably each independently CR 31 , and the plurality of R 31 may be the same as or different from each other.
  • Y 32 , Y 34 and Y 36 are preferably each independently CR 31 , and the plurality of R 31 may be the same or different from each other.
  • the substituted germanium group is preferably represented by —Ge (R 101 ) 3 .
  • R 101 is each independently a substituent.
  • Substituent R 101 is any group selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms. It is preferable that The plurality of R 101 may be the same as or different from each other.
  • the partial structure represented by the general formula (32) has the following as at least one group selected from the group consisting of the groups represented by the following general formulas (35) to (39) and the following general formula (30a). It is preferably included in the three compounds.
  • Y 41 to Y 48 are each independently a nitrogen atom or CR 32 ;
  • Each R 32 is independently a hydrogen atom or a substituent;
  • R 32 as a substituent is each independently A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, A substituted or unsubstituted silyl group, Substituted germanium groups, Substituted phosphine oxide groups, A halogen atom, A
  • the substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms in R 33 is preferably a non-condensed ring.
  • the wavy line part represents a bonding site with another atom or another structure in the molecule of the third compound.
  • Y 41 to Y 48 are preferably each independently CR 32.
  • Y 41 to Y 45 , Y 47 And Y 48 are preferably each independently CR 32.
  • Y 41 , Y 42 , Y 44 , Y 45 , Y 47 and Y 48 are each independently CR 32.
  • Y 42 to Y 48 are preferably each independently CR 32
  • in the general formula (30a) Y 42 to Y 47 are each independently
  • CR 32 is preferable, and the plurality of R 32 may be the same as or different from each other.
  • X 30 is preferably an oxygen atom or a sulfur atom, and more preferably an oxygen atom.
  • R 31 and R 32 are each independently a hydrogen atom or a substituent, and the substituents in R 31 and R 32 are a fluorine atom, a cyano group, a substituted or unsubstituted carbon, Selected from the group consisting of an alkyl group having 1 to 30 carbon atoms, 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 ring atoms. It is preferably any group.
  • R 31 and R 32 are 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. It is more preferable that However, the substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms in R 31 and R 32 is preferably a non-condensed ring.
  • the third compound is preferably an aromatic hydrocarbon compound or an aromatic heterocyclic compound.
  • the third compound preferably does not have a condensed aromatic hydrocarbon ring in the molecule.
  • a 3rd compound can be manufactured by the method as described in international publication 2012/153780, international publication 2013/038650, etc., for example.
  • aromatic hydrocarbon group (sometimes referred to as an aryl group) include a phenyl group, a tolyl group, a xylyl group, a naphthyl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, and a benzo [c] phenanthryl group.
  • 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., preferably phenyl group, biphenyl group, terphenyl group, quarterphenyl group, naphthyl group, triphenylenyl group, fluorenyl group and the like.
  • 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.
  • 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.
  • heterocyclic group (sometimes referred to as heteroaryl group, heteroaromatic ring group, or aromatic heterocyclic group) include pyrrolyl group, pyrazolyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, pyridyl group.
  • Preferred examples 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.
  • the substituted silyl group is preferably a substituted or unsubstituted trialkylsilyl group, a substituted or unsubstituted arylalkylsilyl group, or a substituted or unsubstituted triarylsilyl group.
  • Specific examples of the substituted or unsubstituted trialkylsilyl group include a trimethylsilyl group and a triethylsilyl group.
  • Specific examples of the substituted or unsubstituted arylalkylsilyl group include a diphenylmethylsilyl group, a ditolylmethylsilyl group, and a phenyldimethylsilyl group.
  • Specific examples of the substituted or unsubstituted triarylsilyl group include a triphenylsilyl group and a tolylsilylsilyl group.
  • the substituted phosphine oxide group is preferably a substituted or unsubstituted diarylphosphine oxide group.
  • Specific examples of the substituted or unsubstituted diarylphosphine oxide group include a diphenylphosphine oxide group and a ditolylphosphine oxide group.
  • the third compound is considered to have a function as a dispersion material that suppresses molecular association of the first compounds according to the above-described embodiment in the light emitting layer. Furthermore, the energy from the excited singlet state of the first compound to the excited singlet state of the second compound is increased by separating the distance between the first compound and the second compound by the third compound. As a result of promoting the transfer and suppressing the energy transfer from the excited triplet state of the first compound to the excited triplet state of the second compound, it is presumed that it contributes to the improvement of luminous efficiency.
  • the energy gap T 77K (M1) at 77 [K] of the first compound is preferably larger than the energy gap T 77K (M2) at 77 [K] of the second compound.
  • the energy gap T 77K (M3) at 77 [K] of the third compound is preferably larger than the energy gap T 77K (M1) at 77 [K] of the second compound.
  • the energy gap T 77K (M3) at 77 [K] of the third compound can be measured in the same manner as the first compound and the second compound.
  • the energy gap T 77K (M3) at 77 [K] of the third compound is preferably 2.9 eV or more.
  • the third compound can be hardly involved in exciton generation and carrier transport in the light emitting layer.
  • the light emission efficiency and the light emission color purity can be improved.
  • the organic EL device according to this embodiment for example, when a blue fluorescent compound is used as the second compound, the emission color purity in the blue light emitting region of the organic EL device can be improved. .
  • 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 satisfies the conditions described in the above embodiment.
  • the other light-emitting layer may be a fluorescent light-emitting layer or a phosphorescent light-emitting layer that utilizes light emission by electron transition from a triplet excited state to a direct 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 at least one of the anode side and 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, and excitons.
  • the barrier layer transports electrons, and holes reach a layer on the cathode side of the barrier layer (for example, an electron transport layer).
  • an organic EL element contains an electron carrying layer, it is preferable to contain the said barrier layer between a light emitting layer and an electron carrying layer.
  • the barrier layer transports holes, and the electrons are directed to a layer on the anode side of the barrier layer (for example, a hole transport layer). Stop reaching.
  • the organic EL element includes a hole transport layer
  • 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 and a hole transport layer) closer to the electrode than the barrier layer.
  • the light emitting layer and the barrier layer are preferably joined.
  • Delayed fluorescence emission was confirmed by measuring transient PL using the apparatus shown in FIG.
  • Promp emission immediate observed from the excited state
  • Delay light emission delayed light emission
  • 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).
  • the amount of Prompt luminescence (immediate emission) and X P, the amount of Delay emission (delayed luminescence) is taken as X D, the value of X D / X P means that not less than 0.05.
  • 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”.
  • Compound BH-1 and the compound TH-2 were co-evaporated on a quartz substrate so that the ratio of the compound BH-1 was 12% by mass to form a thin film having a thickness of 100 nm to prepare a sample.
  • 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 a substrate holder of a vacuum evaporation apparatus, and first, the compound HI is vapor-deposited so as to cover the transparent electrode on the surface on which the transparent electrode line is formed. A 5 nm 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 10 nm.
  • Compound EB was vapor-deposited on the second hole transport layer to form a barrier layer having a thickness of 5 nm. Further, on this barrier layer, a compound BH-1 as the first compound, a compound BD-2 as the second compound, and a compound DA-1 as the third compound are co-evaporated to form a film. A light emitting layer having a thickness of 25 nm was formed.
  • the concentration of Compound BH-1 in the light emitting layer was 11% by mass, the concentration of Compound BD-2 was 1% by mass, and the concentration of Compound DA-1 was 88% by mass.
  • Compound HB was vapor-deposited on the light emitting layer to form a 5 nm thick barrier layer.
  • a compound ET was vapor-deposited on the 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.
  • a device arrangement of the organic EL device of Example 1 is schematically shown as follows. ITO (130) / HI (5) / HT-1 (80) / HT-2 (10) / EB (5) / DA-1: BH-1: BD-2 (25, 88%: 11%: 1 %) / HB (5) / ET (20) / LiF (1) / Al (80)
  • the numbers in parentheses indicate the film thickness (unit: nm). Also, in the parentheses, the number displayed as a percentage indicates the ratio (mass%) of each compound in the light emitting layer.
  • Example 2 The organic EL device of Example 2 was produced in the same manner as in Example 1 except that Compound BD-3 was used instead of Compound BD-2 in the light emitting layer of Example 1.
  • a device arrangement of the organic EL device of Example 2 is schematically shown as follows. ITO (130) / HI (5) / HT-1 (80) / HT-2 (10) / EB (5) / DA-1: BH-1: BD-3 (25, 88%: 11%: 1 %) / HB (5) / ET (20) / LiF (1) / Al (80)
  • Example 3 The organic EL device of Example 3 was produced in the same manner as in Example 1 except that Compound BD-4 was used instead of Compound BD-2 in the light emitting layer of Example 1.
  • a device arrangement of the organic EL device of Example 3 is schematically shown as follows. ITO (130) / HI (5) / HT-1 (80) / HT-2 (10) / EB (5) / DA-1: BH-1: BD-4 (25, 88%: 11%: 1 %) / HB (5) / ET (20) / LiF (1) / Al (80)
  • Example 4 The organic EL device of Example 4 was produced in the same manner as in Example 1 except that Compound BD-5 was used instead of Compound BD-2 in the light emitting layer of Example 1.
  • a device arrangement of the organic EL device of Example 4 is schematically shown as follows. ITO (130) / HI (5) / HT-1 (80) / HT-2 (10) / EB (5) / DA-1: BH-1: BD-5 (25, 88%: 11%: 1 %) / HB (5) / ET (20) / LiF (1) / Al (80)
  • Example 5 The organic EL device of Example 5 was produced in the same manner as Example 1 except that Compound BD-6 was used instead of Compound BD-2 in the light emitting layer of Example 1.
  • a device arrangement of the organic EL device of Example 5 is schematically shown as follows. ITO (130) / HI (5) / HT-1 (80) / HT-2 (10) / EB (5) / DA-1: BH-1: BD-6 (25, 88%: 11%: 1 %) / HB (5) / ET (20) / LiF (1) / Al (80)
  • Example 6 The organic EL device of Example 6 was produced in the same manner as in Example 1 except that Compound BD-7 was used instead of Compound BD-2 in the light emitting layer of Example 1.
  • a device arrangement of the organic EL device of Example 6 is schematically shown as follows. ITO (130) / HI (5) / HT-1 (80) / HT-2 (10) / EB (5) / DA-1: BH-1: BD-7 (25, 88%: 11%: 1 %) / HB (5) / ET (20) / LiF (1) / Al (80)
  • Comparative Example 1 The organic EL device of Comparative Example 1 was carried out except that Compound BD-1 was used instead of Compound BD-2 in the light emitting layer of Example 1, and Compound BH-2 was used instead of Compound BH-1. Prepared in the same manner as in Example 1.
  • a device arrangement of the organic EL device of Comparative Example 1 is schematically shown as follows. ITO (130) / HI (5) / HT-1 (80) / HT-2 (10) / EB (5) / DA-1: BH-2: BD-1 (25, 88%: 11%: 1 %) / HB (5) / ET (20) / LiF (1) / Al (80)
  • Comparative Example 2 The organic EL device of Comparative Example 2 was produced in the same manner as in Example 4 except that Compound BH-2 was used instead of Compound BH-1 in the light emitting layer of Example 4.
  • a device arrangement of the organic EL device of Comparative Example 2 is schematically shown as follows. ITO (130) / HI (5) / HT-1 (80) / HT-2 (10) / EB (5) / DA-1: BH-2: BD-5 (25, 88%: 11%: 1 %) / HB (5) / ET (20) / LiF (1) / Al (80)
  • Comparative Example 3 The organic EL device of Comparative Example 3 was produced in the same manner as in Example 5 except that Compound BH-2 was used instead of Compound BH-1 in the light emitting layer of Example 5.
  • a device arrangement of the organic EL device of Comparative Example 3 is schematically shown as follows. ITO (130) / HI (5) / HT-1 (80) / HT-2 (10) / EB (5) / DA-1: BH-2: BD-6 (25, 88%: 11%: 1 %) / HB (5) / ET (20) / LiF (1) / Al (80)
  • Peak emission wavelength ⁇ p The emission peak wavelength ⁇ p was determined from the spectral radiance spectrum obtained above.
  • Example 7 In the organic EL device of Example 7, the compound BD-1 was used in place of the compound BD-2 in the light emitting layer of Example 1, the concentration of BH-1 was 24 mass%, and the concentration of the compound BD-1 was 1 mass. %, And the concentration of Compound DA-1 was 75% by mass.
  • a device arrangement of the organic EL device of Example 7 is schematically shown as follows. ITO (130) / HI (5) / HT-1 (80) / HT-2 (10) / EB (5) / DA-1: BH-1: BD-1 (25, 75%: 24%: 1 %) / HB (5) / ET (20) / LiF (1) / Al (80)
  • Example 8 In the organic EL device of Example 8, the concentration of BH-1 in the light emitting layer of Example 1 was 24% by mass, the concentration of Compound BD-2 was 1% by mass, and the concentration of Compound DA-1 was 75% by mass. The same procedure as in Example 1 was performed except that.
  • a device arrangement of the organic EL device of Example 8 is schematically shown as follows. ITO (130) / HI (5) / HT-1 (80) / HT-2 (10) / EB (5) / DA-1: BH-1: BD-2 (25, 75%: 24%: 1 %) / HB (5) / ET (20) / LiF (1) / Al (80)
  • Example 9 In the organic EL device of Example 9, the concentration of BH-1 in the light emitting layer of Example 2 was 24% by mass, the concentration of Compound BD-3 was 1% by mass, and the concentration of Compound DA-1 was 75% by mass. The same procedure as in Example 2 was performed except that.
  • a device arrangement of the organic EL device of Example 9 is schematically shown as follows. ITO (130) / HI (5) / HT-1 (80) / HT-2 (10) / EB (5) / DA-1: BH-1: BD-3 (25, 75%: 24%: 1 %) / HB (5) / ET (20) / LiF (1) / Al (80)
  • Example 10 In the organic EL device of Example 10, the concentration of BH-1 in the light emitting layer of Example 3 was 24% by mass, the concentration of Compound BD-4 was 1% by mass, and the concentration of Compound DA-1 was 75% by mass. The same procedure as in Example 3 was performed except that.
  • a device arrangement of the organic EL device of Example 10 is schematically shown as follows. ITO (130) / HI (5) / HT-1 (80) / HT-2 (10) / EB (5) / DA-1: BH-1: BD-4 (25, 75%: 24%: 1 %) / HB (5) / ET (20) / LiF (1) / Al (80)
  • Example 11 In the organic EL device of Example 11, the concentration of BH-1 in the light emitting layer of Example 4 was 24% by mass, the concentration of Compound BD-5 was 1% by mass, and the concentration of Compound DA-1 was 75% by mass. The same procedure as in Example 4 was performed except that.
  • a device arrangement of the organic EL device of Example 11 is schematically shown as follows. ITO (130) / HI (5) / HT-1 (80) / HT-2 (10) / EB (5) / DA-1: BH-1: BD-5 (25, 75%: 24%: 1 %) / HB (5) / ET (20) / LiF (1) / Al (80)
  • Example 12 In the organic EL device of Example 12, the concentration of BH-1 in the light emitting layer of Example 5 was 24% by mass, the concentration of Compound BD-6 was 1% by mass, and the concentration of Compound DA-1 was 75% by mass. The same procedure as in Example 5 was performed except that.
  • a device arrangement of the organic EL device of Example 12 is schematically shown as follows. ITO (130) / HI (5) / HT-1 (80) / HT-2 (10) / EB (5) / DA-1: BH-1: BD-6 (25, 75%: 24%: 1 %) / HB (5) / ET (20) / LiF (1) / Al (80)
  • Example 13 In the organic EL device of Example 13, the concentration of BH-1 in the light emitting layer of Example 6 was 24% by mass, the concentration of Compound BD-7 was 1% by mass, and the concentration of Compound DA-1 was 75% by mass. The same procedure as in Example 6 was performed except that.
  • a device arrangement of the organic EL device of Example 13 is schematically shown as follows. ITO (130) / HI (5) / HT-1 (80) / HT-2 (10) / EB (5) / DA-1: BH-1: BD-7 (25, 75%: 24%: 1 %) / HB (5) / ET (20) / LiF (1) / Al (80)
  • Comparative Example 4 The organic EL device of Comparative Example 4 was produced in the same manner as in Example 7 except that Compound BH-2 was used instead of Compound BH-1 in the light emitting layer of Example 7.
  • a device arrangement of the organic EL device of Comparative Example 4 is schematically shown as follows. ITO (130) / HI (5) / HT-1 (80) / HT-2 (10) / EB (5) / DA-1: BH-2: BD-1 (25, 75%: 24%: 1 %) / HB (5) / ET (20) / LiF (1) / Al (80)
  • Comparative Example 5 The organic EL device of Comparative Example 5 was produced in the same manner as in Example 11 except that Compound BH-2 was used instead of Compound BH-1 in the light emitting layer of Example 11.
  • a device arrangement of the organic EL device of Comparative Example 5 is schematically shown as follows. ITO (130) / HI (5) / HT-1 (80) / HT-2 (10) / EB (5) / DA-1: BH-2: BD-5 (25, 75%: 24%: 1 %) / HB (5) / ET (20) / LiF (1) / Al (80)
  • Comparative Example 6 The organic EL device of Comparative Example 6 was produced in the same manner as in Example 12 except that Compound BH-2 was used instead of Compound BH-1 in the light emitting layer of Example 12.
  • a device arrangement of the organic EL device of Comparative Example 6 is schematically shown as follows. ITO (130) / HI (5) / HT-1 (80) / HT-2 (10) / EB (5) / DA-1: BH-2: BD-6 (25, 75%: 24%: 1 %) / HB (5) / ET (20) / LiF (1) / Al (80)
  • Example 14 In the organic EL device of Example 14, the compound BD-1 was used in place of the compound BD-2 in the light emitting layer of Example 1, the concentration of BH-1 in the light emitting layer of Example 1 was 49% by mass, and the compound BD It was prepared in the same manner as in Example 1 except that the concentration of -1 was 1% by mass and the concentration of compound DA-1 was 50% by mass.
  • a device arrangement of the organic EL device of Example 14 is schematically shown as follows.
  • Example 15 In the organic EL device of Example 15, the concentration of BH-1 in the light emitting layer of Example 1 was 49% by mass, the concentration of Compound BD-2 was 1% by mass, and the concentration of Compound DA-1 was 50% by mass. The same procedure as in Example 1 was performed except that.
  • a device arrangement of the organic EL device of Example 15 is schematically shown as follows. ITO (130) / HI (5) / HT-1 (80) / HT-2 (10) / EB (5) / DA-1: BH-1: BD-2 (25, 50%: 49%: 1 %) / HB (5) / ET (20) / LiF (1) / Al (80)
  • Example 16 In the organic EL device of Example 16, the concentration of BH-1 in the light emitting layer of Example 2 was 49% by mass, the concentration of Compound BD-3 was 1% by mass, and the concentration of Compound DA-1 was 50% by mass. The same procedure as in Example 2 was performed except that.
  • a device arrangement of the organic EL device of Example 16 is schematically shown as follows. ITO (130) / HI (5) / HT-1 (80) / HT-2 (10) / EB (5) / DA-1: BH-1: BD-3 (25, 50%: 49%: 1 %) / HB (5) / ET (20) / LiF (1) / Al (80)
  • Example 17 In the organic EL device of Example 17, the concentration of BH-1 in the light emitting layer of Example 3 was 49% by mass, the concentration of Compound BD-4 was 1% by mass, and the concentration of Compound DA-1 was 50% by mass. The same procedure as in Example 3 was performed except that.
  • a device arrangement of the organic EL device of Example 17 is schematically shown as follows. ITO (130) / HI (5) / HT-1 (80) / HT-2 (10) / EB (5) / DA-1: BH-1: BD-4 (25, 50%: 49%: 1 %) / HB (5) / ET (20) / LiF (1) / Al (80)
  • Example 18 In the organic EL device of Example 18, the concentration of BH-1 in the light emitting layer of Example 4 was 49% by mass, the concentration of Compound BD-5 was 1% by mass, and the concentration of Compound DA-1 was 50% by mass. The same procedure as in Example 4 was performed except that.
  • a device arrangement of the organic EL device of Example 18 is schematically shown as follows. ITO (130) / HI (5) / HT-1 (80) / HT-2 (10) / EB (5) / DA-1: BH-1: BD-5 (25, 50%: 49%: 1 %) / HB (5) / ET (20) / LiF (1) / Al (80)
  • Example 19 In the organic EL device of Example 19, the concentration of BH-1 in the light emitting layer of Example 5 was 49% by mass, the concentration of Compound BD-6 was 1% by mass, and the concentration of Compound DA-1 was 50% by mass. The same procedure as in Example 5 was performed except that.
  • a device arrangement of the organic EL device of Example 19 is schematically shown as follows. ITO (130) / HI (5) / HT-1 (80) / HT-2 (10) / EB (5) / DA-1: BH-1: BD-6 (25, 50%: 49%: 1 %) / HB (5) / ET (20) / LiF (1) / Al (80)
  • Example 20 In the organic EL device of Example 20, the concentration of BH-1 in the light emitting layer of Example 6 was 49% by mass, the concentration of Compound BD-7 was 1% by mass, and the concentration of Compound DA-1 was 50% by mass. The same procedure as in Example 6 was performed except that.
  • a device arrangement of the organic EL device of Example 20 is roughly shown as follows. ITO (130) / HI (5) / HT-1 (80) / HT-2 (10) / EB (5) / DA-1: BH-1: BD-7 (25, 50%: 49%: 1 %) / HB (5) / ET (20) / LiF (1) / Al (80)
  • Comparative Example 7 The organic EL device of Comparative Example 7 did not use Compound BD-2 in the light emitting layer of Example 1, except that the concentration of BH-1 was 12% by mass and the concentration of Compound DA-1 was 88% by mass. It was produced in the same manner as in Example 1.
  • a device arrangement of the organic EL device of Comparative Example 7 is schematically shown as follows. ITO (130) / HI (5) / HT-1 (80) / HT-2 (10) / EB (5) / DA-1: BH-1 (25, 88%: 12%) / HB (5) / ET (20) / LiF (1) / Al (80)
  • Comparative Example 8 The organic EL device of Comparative Example 8 did not use Compound BD-1 in the light emitting layer of Example 7, except that the concentration of BH-1 was 25 mass% and the concentration of Compound DA-1 was 75 mass%. It was produced in the same manner as in Example 7.
  • a device arrangement of the organic EL device of Comparative Example 8 is schematically shown as follows. ITO (130) / HI (5) / HT-1 (80) / HT-2 (10) / EB (5) / DA-1: BH-1 (25, 75%: 25%) / HB (5) / ET (20) / LiF (1) / Al (80)
  • Example 9 In the organic EL device of Comparative Example 9, the compound BD-1 was not used in the light-emitting layer of Example 14, except that the concentration of BH-1 was 50 mass% and the concentration of compound DA-1 was 50 mass%. It was produced in the same manner as in Example 14.
  • a device arrangement of the organic EL device of Comparative Example 9 is schematically shown as follows. ITO (130) / HI (5) / HT-1 (80) / HT-2 (10) / EB (5) / DA-1: BH-1 (25, 50%: 50%) / HB (5) / ET (20) / LiF (1) / Al (80)
  • the organic EL elements according to Examples 1 to 20 are more than the organic EL elements according to Comparative Examples 7 to 9 that emit BH-1, which is a delayed fluorescent material. Blue light emission with high color purity was obtained. As described above, it was found that the organic EL elements according to Examples 1 to 20 have improved luminous efficiency and color purity.

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Abstract

L'invention concerne un élément électroluminescent organique comprenant une anode, une couche électroluminescente, et une cathode, la couche électroluminescente comprenant un premier composé ayant des propriétés de fluorescence retardée représenté par la formule générale (1) et un second composé ayant des propriétés d'émission de fluorescence.
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CN110892541A (zh) * 2017-07-10 2020-03-17 东丽株式会社 发光元件、包含该发光元件的显示器、照明装置及传感器
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