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WO2019009307A1 - Composition pour former un élément oled, et élément oled - Google Patents

Composition pour former un élément oled, et élément oled Download PDF

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Publication number
WO2019009307A1
WO2019009307A1 PCT/JP2018/025274 JP2018025274W WO2019009307A1 WO 2019009307 A1 WO2019009307 A1 WO 2019009307A1 JP 2018025274 W JP2018025274 W JP 2018025274W WO 2019009307 A1 WO2019009307 A1 WO 2019009307A1
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Prior art keywords
light emitting
less
forming
layer
composition
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English (en)
Japanese (ja)
Inventor
王己 高
淑 杉山
マーダー，セス
キッペレン，バーナード
バーロウ，スティーブン
フエンテス－ヘルナンデス，カネック
チャング，シャオチン
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Mitsubishi Chemical Corp
Georgia Tech Research Institute
Georgia Tech Research Corp
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Mitsubishi Chemical Corp
Georgia Tech Research Institute
Georgia Tech Research Corp
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Priority to JP2019527730A priority Critical patent/JPWO2019009307A1/ja
Publication of WO2019009307A1 publication Critical patent/WO2019009307A1/fr
Anticipated expiration legal-status Critical
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    • 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
    • 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

Definitions

  • the present invention relates to a composition for forming an OLED element and an OLED element.
  • the light emitting layer of an OLED is generally formed of a two-component system of a charge transporting material (host material) responsible for transporting holes and electrons and a light emitting material (dopant material) responsible for light emission.
  • a charge transporting material responsible for transporting holes and electrons
  • a light emitting material responsible for light emission.
  • Non-Patent Documents 1 to 3 it has also been reported that a compound having TADF performance is used as a charge transport material instead of a light emitting material.
  • a compound exhibiting TADF performance When a compound exhibiting TADF performance is used as a light-emitting material to emit blue light, there is a problem called roll-off in which the electroluminescent quantum efficiency (EQE) sharply decreases as the current density increases.
  • the present invention solves the problem of roll-off, and provides an OLED element exhibiting high EQE even at high current density and / or high luminance (for example, initial luminance of 100 cd / m 2 or more, preferably about 1000 cd / m 2 ). To be a task.
  • the present inventors attempted to use a compound that exhibits TADF performance as the charge transport material in addition to the light emitting material.
  • the above problem is caused by using, as the light-emitting material and the charge-transporting material, a compound having TADF performance whose absolute value ( ⁇ E st ) of the energy difference between excited singlet energy and excited triplet energy is 0.37 eV or less. It was found that the problem was solved, and the first invention was completed.
  • the excitation singlet energy E gs1 emitting material, the use of the charge transporting material of the excited singlet energy E hs1, and compositions triplet energy E ht1 is a particular relationship between the charge-transporting material, the It has been found that the problem is solved, and the second invention has been completed.
  • a composition for forming an OLED device comprising a light emitting material and a charge transporting material, The light emitting material and the charge transport material both have TADF performance, The charge transport material has an absolute value ⁇ E st of an energy difference between excited singlet energy and excited triplet energy of 0.37 eV or less
  • a composition for forming an OLED element wherein the difference between the light emission peak wavelength of the charge transport material and the absorption peak wavelength on the longest wavelength side of the light emitting material is 95 nm or less.
  • the luminescent material, the absolute value Delta] E st of the energy difference between the excited singlet energy and triplet energy is less than 0.37 eV, OLED element forming composition as described in (1).
  • composition for forming an OLED element according to (1) or (2) wherein the emission wavelength of the charge transport material is 465 nm or less.
  • ⁇ E st of the charge transport material is 0.1 eV or less.
  • a composition for forming an OLED device comprising a light emitting material and a charge transporting material,
  • the light emitting material and the charge transport material both have TADF performance
  • the luminescent material excited singlet energy E gs1, the charge transporting material of the excited singlet energy E hs1, and triplet energy E ht1 of the charge transporting material satisfy the following relations, OLED element forming composition . (E hs1 -E gs1 ) / (E hs1 -E ht1 ) ⁇ 1.1 (7)
  • a composition for forming an OLED element comprising a light emitting material and a charge transporting material, The light emitting material and the charge transport material both have TADF performance, The light emitting material has a light emission wavelength of 500 nm or less, and an absolute value ( ⁇ E st ) of an energy difference between the excitation singlet energy and the excitation triplet energy is 0.37 eV or less.
  • the composition for forming an OLED element wherein the charge transport material has an emission wavelength of 465 nm or less and an absolute value ( ⁇ E st ) of an energy difference between excited singlet energy and excited triplet energy of 0.37 eV or less.
  • a composition for forming an OLED element comprising a light emitting material and a charge transporting material,
  • the light emitting material and the charge transport material both have TADF performance,
  • the light emitting material has a light emitting wavelength of 500 nm or less, and the charge transport material has a light emitting wavelength of 465 nm or less.
  • the luminescent material excited singlet energy E gs1, the charge transporting material of the excited singlet energy E hs1, and triplet energy E ht1 satisfy the following relations, OLED element forming composition.
  • the present invention it is possible to solve the roll-off problem and provide an OLED element that exhibits high current density and / or high EQE even at high brightness.
  • composition for forming an OLED element that is an embodiment of the present invention contains a light emitting material (dopant material) and a charge transporting material (host material).
  • the composition for forming an OLED element may contain materials other than the light emitting material and the charge transport material, and may contain, for example, a solvent.
  • a light emitting material having TADF performance means, in the light emitting material, a thermally active type using reverse intersystem crossing (RICS) from triplet excitons to singlet excitons.
  • RCS reverse intersystem crossing
  • TADF Thermally Activated Delayed Fluorescence
  • charge transport materials having TADF performance cause reverse intersystem crossing (RICS) from triplet excitons to singlet excitons by thermal activation, and singlet excitons further undergo Ferster resonance energy transfer ( FRET: A compound exhibiting the ability to move to a singlet of a light emitting material by means of Forster Resonance Energy Transfer).
  • a compound having TADF performance is used as a light emitting material, but also a compound having TADF performance is used as a charge transport material.
  • a compound having TADF performance is used as both the light emitting material and the charge transport material, it is possible to solve the roll-off problem and provide an OLED element exhibiting high EQE even at high current density and / or high luminance.
  • the inventors consider as follows the reason why the roll-off problem can be solved by using a compound having TADF performance as both the light emitting material and the charge transporting material.
  • the main physical cause that causes the roll-off problem is triplet-triplet annihilation (TTA). That is, in the high drive current region, due to the high density distribution of excitons generated in the triplets of the charge transport material, the triplet-triplet exciton annihilation between charge transport molecules present in a narrow region becomes remarkable Cause roll-off problems.
  • TTA triplet-triplet annihilation
  • excitons generated in the triplet of the charge transport material are quickly transferred to singlets, and further transferred from singlets of the charge transport material to singlets of the light emitting material. Triplet-triplet exciton annihilation is mitigated, leading to a solution of the roll-off problem.
  • the composition for forming an OLED element in the first embodiment of the present invention is a composition for forming an OLED element containing a light emitting material and a charge transporting material, and the light emitting material and the charge transporting material both have TADF performance.
  • charge transport materials, the absolute value Delta] E st of the energy difference between the excited singlet energy and triplet energy is less than or equal 0.37 eV, and the emission peak wavelength of the charge transport material, the longest wavelength of the luminescent material
  • the difference of the absorption peak wavelength on the side is 95 nm or less.
  • the light emitting material in the first embodiment of the present invention is a compound having TADF performance.
  • the light emission wavelength ( ⁇ em) of the light emitting material is not particularly limited, but is preferably 500 nm or less, that is, the light emitting material is preferably a blue light emitting compound.
  • the upper limit of the emission wavelength of the light emitting material may be 490 nm or less, 485 nm or less, or 480 nm or less.
  • the lower limit of the emission wavelength is not particularly limited, but may be 400 nm or more, 410 nm or more, 420 nm or more, 425 nm or more, 450 nm or more, 460 nm or more It may well be 470 nm or more.
  • the emission wavelength of the light emitting material means a wavelength showing a peak intensity in the spectral distribution of light emitted by the light emitting material.
  • the light emitting material used in the present embodiment is preferably a compound having TADF performance, and the absolute value ( ⁇ E st ) of the energy difference between the excited singlet energy and the excited triplet energy is 0.37 eV or less.
  • ⁇ E st the absolute value of the energy difference between the excited singlet energy and the excited triplet energy is 0.37 eV or less.
  • the upper limit value of ⁇ E st of the light emitting material may be 0.36 eV or less, 0.35 eV or less, 0.34 eV or less, 0.33 eV or less, and 0.32 eV or less , May be 0.31 eV or less, may be 0.30 eV or less, may be 0.20 eV or less, may be 0.18 eV or less, and may be 0.15 eV or less. It may be 0.13 eV or less and 0.10 eV or less.
  • the lower limit value of ⁇ E st of the light emitting material is not particularly limited, but may usually be larger than 0 eV, may be 0.01 eV or more, may be 0.02 eV or more, and may be 0.03 eV or more.
  • the excitation singlet energy of the light emitting material is determined from the rising wavelength on the short wavelength side of the emission spectrum of the toluene solution of the light emitting material at room temperature.
  • the excitation triplet energy of the light emitting material is determined from the rising wavelength on the short wavelength side of the emission spectrum at 77 K of the toluene solution of the light emitting material.
  • the rising wavelength on the short wavelength side is determined as follows.
  • the emission spectrum is shown with the horizontal axis as the wavelength and the vertical axis as the emission intensity, and when the tangent line is drawn from the emission peak wavelength on the shortest wavelength side to each short wavelength direction, the slope is the most A tangent at a wavelength at which the wavelength becomes large is a rising tangent.
  • a tangent drawn to a spectrum of a substantially non-emitting wavelength region shorter than the wavelength at which the rising tangent is obtained is taken as a baseline tangent.
  • the wavelength at the intersection of the rising tangent and the baseline tangent determined in this manner is taken as the rising wavelength.
  • the excited singlet energy and the excited triplet energy of the light emitting material can be obtained by converting the corresponding rising wavelength into an eV unit.
  • the charge transport material in the first embodiment of the present invention is a compound having TADF performance, and preferably has an emission wavelength ( ⁇ em) of 465 nm or less. That is, the charge transport material is preferably a blue light emitting compound.
  • the emission wavelength of the charge transport material may be 460 nm or less, 450 nm or less, 445 nm or less, 420 nm or less, or 410 nm or less.
  • the lower limit of the emission wavelength is not particularly limited, but may be 400 nm or more, 410 nm or more, 420 nm or more, or 425 nm or more.
  • the emission wavelength of the charge transport material means a wavelength showing a peak intensity in the spectral distribution of the light emitted by the charge transport material.
  • the charge transport material used in this embodiment is a compound having TADF performance, and the absolute value ( ⁇ E st ) of the energy difference between the excited singlet energy and the excited triplet energy is usually 0.37 eV or less.
  • ⁇ E st the absolute value of the energy difference between the excited singlet energy and the excited triplet energy.
  • the upper limit value of ⁇ E st of the charge transport material may be preferably 0.36 eV or less, may be 0.35 eV or less, may be 0.34 eV or less, may be 0.33 eV or less, and 0.
  • the lower limit value of ⁇ E st of the charge transport material is not particularly limited, but may usually be larger than 0 eV, may be 0.01 eV or more, may be 0.02 eV or more, and may be 0.03 eV or more.
  • the excited singlet energy and the excited triplet energy of the charge transport material can be determined in the same manner as the excited singlet energy and the excited triplet energy of the light emitting material, respectively.
  • the charge transport material in which the value of the charge transport material ⁇ E st satisfies the above range will be described later. Similar to the light emitting material, the charge transport material can be selected based on the finding that the twist between the donor portion and the acceptor portion of the compound and the charge transport material ⁇ E st correlate with each other.
  • Another aspect of the first embodiment of the present invention is to provide a method for designing or manufacturing an OLED element using a composition for forming an OLED element containing a light emitting material and a charge transport material.
  • Design method or the manufacturing method of an OLED device according the excited singlet energy E of the charge transport material hs1, and triplet energy E ht1 charge transporting materials, the excited singlet energy E gs1 emitting material, the following relationship Selecting the light emitting material and the charge transporting material to be satisfied.
  • the step of mixing the selected light emitting material and charge transport material, the step of forming a light emitting layer from the composition for forming an OLED element, and the like may be included.
  • the ratio of (E hs1 -E gs1 ) / (E hs1 -E ht1 ) represented by the above relational expression is 1.1 or more, preferably 1.2 or more, and preferably 1.3 or more.
  • it is 1.4 or more, more preferably 1.5 or more, still more preferably 1.55 or more, still more preferably 1.6 or more, 1.7 or more Is particularly preferred, and 2.0 or more is most preferred.
  • the upper limit is not particularly limited, and may be 5.0 or less, may be 4.5 or less, may be 4.0 or less, 3.0 or less, or 2.0 or less. May be there.
  • both the light emitting material and the charge transport material are specific compounds having TADF performance.
  • the structure is not particularly limited as long as the effects of the present invention are not significantly impaired.
  • aryl group eg, phenyl group, naphthyl group, anthryl group, tolyl group, xylyl group, phenanthryl group, fluorenyl group, pyrenyl group, chrysenyl group, fluoranthenyl group, benzo [a] anthryl group, benzo [c] phenanthryl Group, triphenylenyl group, benzo [k] fluoranthenyl group, benzo [g] chrysenyl group, benzo [b] triphenylenyl group, picenyl group, perylenyl group, rubrenyl group etc., heteroaryl group (eg pyridyl group, pyrimidinyl group, Furyl group, pyrrolyl group, imidazolyl group, benzimidazolyl group, pyrazolyl group, pyrazinyl group, triazolyl group, oxazolyl group, benzoxazo
  • a carbazolyl group an arylsulfonyl group or a heteroarylsulfonyl group.
  • Having a carbazolyl group tends to be able to retain relatively high triplet energy while exhibiting relatively good hole transportability.
  • By having an arylsulfonyl group or a heteroarylsulfonyl group it tends to be possible to have a low ⁇ E st while retaining high triplet energy. Low ⁇ E st is preferable to obtain the effects of the present invention.
  • the aryl of the arylsulfonyl group or the heteroaryl of the heteroarylsulfonyl group is not particularly limited, and examples thereof include a 5- or 6-membered monocyclic ring or a ring in which 2 or 3 rings are fused.
  • the number of carbon atoms is not particularly limited, but is preferably 5 or more and 30 or less, and more preferably 20 or less.
  • divalent cyclopenteetadiene benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, fluorene ring, pyrene ring, chrysene ring, fluoranthene ring, perylene ring, rubrene ring, triphenylene ring, picene ring, etc.
  • divalent cyclopenteetadiene benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, fluorene ring, pyrene ring, chrysene ring, fluoranthene ring, perylene ring, rubrene ring, triphenylene ring, picene ring, etc.
  • the carbazolyl group, the arylsulfonyl group or the heteroarylsulfonyl group may have a substituent, and is an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryl group having 1 to 30 carbon atoms, carbon
  • the heteroaryl groups of the formulas 1 to 30, a cyano group, a fluorine atom and the like can be mentioned.
  • a specific example is shown, it is not limited to this.
  • preferable ones as a light emitting material are as follows.
  • charge transport material preferred as the charge transport material are as follows.
  • the difference between the emission peak wavelength of the charge transport material and the absorption peak wavelength on the longest wavelength side of the light emitting material is usually 95 nm or less, preferably 90 nm or less, more preferably 86 nm or less It is preferably 80 nm or less, particularly preferably 70 nm or less, most preferably 68 nm or less, and usually 0 nm or more, preferably 10 nm or more, more preferably 20 nm, still more preferably 25 nm or more .
  • the absorption peak wavelength of the light emitting material is a wavelength that shows the absorption maximum at the longest wavelength side in the absorption spectrum of the light emitting material in the visible wavelength range.
  • the wavelength of the shoulder is taken as the absorption peak wavelength.
  • the slope of the tangent at each wavelength of 380 nm to 780 nm is determined.
  • the absorbance of the light emitting material is measured every 1 nm from 375 nm to 785 nm, and the abscissa represents the wavelength and the ordinate represents the absorbance, thereby obtaining a visible absorption spectrum.
  • the slope of the tangent of each wavelength is the following formula (ABS (+5 nm)-ABS (-5 nm)) / 10 Calculated by When the slope of the tangent is viewed from the long wavelength side to the short wavelength side, the slope of the tangent is zero in a wavelength region where there is no light absorption from 780 nm to the rising of the absorption peak. At the rising wavelength of the absorption peak, the slope of the tangent turns from zero to a negative value.
  • the absolute value of the slope of the tangent line gradually increases from the rising wavelength of the absorption peak toward the short wavelength side, gradually decreases at the inflection point, and becomes zero at the absorption maximum wavelength.
  • the slope of the tangent turns to a positive value at the absorption maximum wavelength.
  • the absorption maximum wavelength at which the absolute value of the slope of the tangent line is zero is taken as the absorption peak wavelength on the longest wavelength side of the light emitting material.
  • another inflection point is added to the absorption peak between the rising of the absorption peak and the inflection point (referred to as the first inflection point). It will be considered as a turning point).
  • the absolute value of the slope of the tangent gradually increases from the rising of the absorption peak toward the short wavelength side, and the absolute value of the slope of the tangent gradually decreases at the second inflection point. It becomes a value.
  • the minimum value is a value larger than zero.
  • the absolute value of the slope of the tangent gradually increases toward the short wavelength side from the wavelength at which the minimum value is obtained, and reaches the first inflection point. On the shorter wavelength side than the first inflection point, the slope of the tangent exhibits the same behavior as in the case where the absorption peak has no shoulder.
  • the wavelength at which the absolute value of the slope of the tangent is a minimum value is taken as the absorption peak wavelength on the longest wavelength side of the light emitting material.
  • the composition for forming an OLED element in the second embodiment of the present invention is a composition for forming an OLED element containing a light emitting material and a charge transporting material, and the light emitting material and the charge transporting material both have TADF performance.
  • Light emitting material As the light emitting material in the second embodiment of the present invention, the same light emitting material as in the first embodiment of the present invention can be used. The preferable aspects of the light emitting material in the second embodiment of the present invention are also the same as the light emitting material in the first embodiment of the present invention.
  • charge transport material As the charge transport material in the second embodiment of the present invention, the same one as the charge transport material in the first embodiment of the present invention can be used except that ⁇ E st is not limited to 0.37 eV or less. . Preferred aspects of the charge transport material in the second embodiment of the present invention are also the same as the charge transport material in the first embodiment of the present invention.
  • the difference between the emission peak wavelength and the absorption peak wavelength The difference between the emission peak wavelength of the charge transport material in the second embodiment of the present invention and the absorption peak wavelength on the longest wavelength side of the light emitting material is not particularly limited, but is preferably 95 nm. Other preferable values are the same as the difference between the emission peak wavelength of the charge transport material in the second embodiment of the present invention and the absorption peak wavelength on the longest wavelength side of the light emitting material. Further, the method of determining the absorption peak wavelength of the light emitting material (dopant material) is also the same as the method of determination in the first embodiment of the present invention.
  • Another aspect of the second embodiment of the present invention is to provide a method for designing or manufacturing an OLED element using a composition for forming an OLED element containing a light emitting material and a charge transporting material.
  • Design method or the manufacturing method of an OLED device according the excited singlet energy E of the charge transport material hs1, and triplet energy E ht1 charge transporting materials, the excited singlet energy E gs1 emitting material, the following relationship Selecting the light emitting material and the charge transporting material to be satisfied.
  • the step of mixing the selected light emitting material and charge transport material, the step of forming a light emitting layer from the composition for forming an OLED element, and the like may be included.
  • the ratio of (E hs1 -E gs1 ) / (E hs1 -E ht1 ) represented by the above relational expression is 1.1 or more, preferably 1.2 or more, and preferably 1.3 or more.
  • it is 1.4 or more, more preferably 1.5 or more, still more preferably 1.55 or more, still more preferably 1.6 or more, 1.7 or more Is particularly preferred, and 2.0 or more is most preferred.
  • the upper limit is not particularly limited, and may be 5.0 or less, may be 4.5 or less, may be 4.0 or less, 3.0 or less, or 2.0 or less. May be there.
  • FIG. 1 is a schematic cross-sectional view showing the structure of the OLED element 10.
  • the OLED device 10 comprises an anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, a hole blocking layer 6, an electron transport layer 7, an electron injection layer 8 and a cathode 9 in this order on a substrate 1. It has a multilayer structure which is laminated.
  • the substrate 1 is a support of the OLED element 10, and usually, a plate of quartz or glass, a metal plate, a metal foil, a plastic film, a sheet or the like is used. Among these, a glass plate or a plate of a transparent synthetic resin such as polyester, polymethacrylate, polycarbonate, polysulfone or the like is preferable.
  • the substrate is preferably made of a material having high gas barrier properties, since the OLED element is less likely to deteriorate due to the open air. When using a material having low gas barrier properties, such as a synthetic resin substrate, it is preferable to increase the gas barrier properties by providing a dense silicon oxide film or the like on at least one side of the substrate.
  • the anode 2 has a function of injecting holes into the layer on the light emitting layer 5 side.
  • the anode 2 is usually a metal such as aluminum, gold, silver, nickel, palladium or platinum; a metal oxide such as indium oxide, tin oxide or indium tin oxide (ITO); a metal halide such as copper iodide; carbon Black; conductive polymer such as poly (3-methylthiophene), polypyrrole, polyaniline and the like; and the like.
  • the formation of the anode 2 is usually performed by a dry method such as a sputtering method or a vacuum evaporation method in many cases.
  • a dry method such as a sputtering method or a vacuum evaporation method in many cases.
  • metal fine particles such as silver, fine particles such as copper iodide, carbon black, conductive metal oxide fine particles, conductive polymer fine powder, etc.
  • an appropriate binder resin solution it can also be formed by dispersing and coating on a substrate.
  • a conductive polymer a thin film can be directly formed on a substrate by electrolytic polymerization, or a conductive polymer can be coated on the substrate to form an anode (Appl. Phys. Lett., 60) Volume, 2711 (1992).
  • the anode 2 usually has a single layer structure, but may have a laminated structure as appropriate. When the anode 2 has a laminated structure, different conductive materials may be laminated on the first-layer anode.
  • the thickness of the anode 2 may be determined according to the required transparency, the material, and the like. In particular, when high transparency is required, the thickness is preferably such that the visible light transmittance is 60% or more, and more preferably 80% or more.
  • the thickness of the anode 2 is usually 5 nm or more, preferably 10 nm or more, and is usually 1000 nm or less, preferably 500 nm or less.
  • the thickness of the anode 2 may be arbitrarily set in accordance with the required strength and the like. In this case, the anode 2 may have the same thickness as the substrate.
  • the impurities on the anode 2 are removed and the ionization potential is adjusted by ultraviolet / ozone treatment, oxygen plasma treatment, argon plasma treatment, etc. before film formation. It is preferable to improve the hole injection property.
  • the layer responsible for transporting holes from the anode 2 side to the light emitting layer 5 side is usually called a hole injecting and transporting layer or a hole transporting layer. Then, when there are two or more layers that have the function of transporting holes from the anode 2 side to the light emitting layer 5 side, the layer closer to the anode side may be called the hole injection layer 3.
  • the hole injection layer 3 is preferably formed in order to enhance the function of transporting holes from the anode 2 to the light emitting layer 5 side. When forming the hole injection layer 3, the hole injection layer 3 is usually formed on the anode 2.
  • the thickness of the hole injection layer 3 is usually 1 nm or more, preferably 5 nm or more, and usually 1000 nm or less, preferably 500 nm or less.
  • the hole injection layer may be formed by a vacuum evaporation method or a wet film formation method. It is preferable to form by a wet film-forming method at the point which is excellent in the film-forming property.
  • the hole injecting layer 3 preferably contains a hole transporting compound, and more preferably contains a hole transporting compound and an electron accepting compound. Furthermore, it is preferable to include a cation radical compound in the hole injection layer, and it is particularly preferable to include a cation radical compound and a hole transporting compound.
  • hole transporting compound a compound having an ionization potential of 4.5 eV to 6.0 eV is preferable as the hole transporting compound.
  • hole transporting compounds include aromatic amine compounds, phthalocyanine compounds, porphyrin compounds, oligothiophene compounds, polythiophene compounds, benzylphenyl compounds, compounds in which tertiary amines are linked by a fluorene group, hydrazones And compounds such as silazane compounds and quinacridone compounds.
  • aromatic amine compounds are preferable, and aromatic tertiary amine compounds are particularly preferable, from the viewpoint of amorphousness and visible light transparency.
  • the aromatic tertiary amine compound is a compound having an aromatic tertiary amine structure, and also includes a compound having a group derived from an aromatic tertiary amine.
  • the type of aromatic tertiary amine compound is not particularly limited, but a polymer compound having a weight average molecular weight of 1,000 or more and 1,000,000 or less (a polymerizable compound in which repeating units are continuous, from the viewpoint of obtaining uniform light emission due to surface smoothing effect. It is preferred to use As a preferable example of an aromatic tertiary amine polymer compound, the polymer compound etc. which have a repeating unit represented by following formula (10) are mentioned.
  • Ar 11 and Ar 12 each independently represent an aromatic hydrocarbon group which may have a substituent or an aromatic heterocyclic group which may have a substituent.
  • Ar 13 to Ar 15 each independently represent an aromatic hydrocarbon group which may have a substituent or an aromatic heterocyclic group which may have a substituent.
  • Y represents a linking group selected from the group of linking groups shown below. Further, two groups bonded to the same N atom among Ar 11 to Ar 15 may bond to each other to form a ring.
  • Ar 16 to Ar 26 each independently represent an aromatic hydrocarbon group which may have a substituent or an aromatic heterocyclic group which may have a substituent.
  • R 11 and R 12 independently represents a hydrogen atom or an optional substituent.
  • the aromatic hydrocarbon group and the aromatic heterocyclic group of Ar 16 to Ar 26 have one or two free valences from the viewpoint of solubility of the polymer compound, heat resistance, and hole injection transportability.
  • a benzene ring, a naphthalene ring, a phenanthrene ring, a thiophene ring and a pyridine ring are preferable, and a benzene ring and a naphthalene ring having a free valence of 1 or 2 are more preferable.
  • aromatic tertiary amine polymer compound having a repeating unit represented by the formula (10) include those described in WO 2005/089024.
  • the conductivity of the hole injecting layer 3 can be improved by oxidation of the hole transporting compound, so that the hole injecting layer 3 contains the electron accepting compound described above and the cation radical compound described above. Is preferred.
  • Cationic radical compounds derived from high molecular weight compounds such as PEDOT / PSS (Adv. Mater., 2000, 12, 481) and emeraldine hydrochloride (J. Phys. Chem., 1990, 94, 7716) It is also produced by oxidative polymerization (dehydrogenation polymerization).
  • the oxidative polymerization referred to herein is to oxidize a monomer chemically or electrochemically in an acidic solution using a peroxodisulfate or the like.
  • the monomer is polymerized by oxidation, and the cation radical which is obtained by removing one electron from the repeating unit of the polymer having the anion derived from the acidic solution as a counter anion is Generate
  • a composition for forming a film (hole) is usually mixed with a material to be the hole injection layer with a soluble solvent (solvent for the hole injection layer)
  • a soluble solvent solvent for the hole injection layer
  • the composition for forming an injection layer is prepared, and the composition for forming a hole injection layer is applied onto a layer (usually, an anode) corresponding to the lower layer of the hole injection layer to form a film, and then dried.
  • the concentration of the hole transporting compound in the composition for forming a hole injection layer is optional as long as the effects of the present invention are not significantly impaired, but in terms of film thickness uniformity, lower is preferable, and It is preferable that the height is higher in that defects are less likely to occur in the hole injection layer.
  • the content is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, particularly preferably 0.5% by mass or more, and 70% by mass
  • the content is preferably the following, more preferably 60% by mass or less, and particularly preferably 50% by mass or less.
  • Examples of the solvent for the hole injection layer include ether solvents, ester solvents, aromatic hydrocarbon solvents, amide solvents and the like.
  • ether solvents include aliphatic ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol-1-monomethyl ether acetate (PGMEA); 1,2-dimethoxybenzene, 1,3-dimethoxybenzene, anisole And aromatic ethers such as phenetole, 2-methoxytoluene, 3-methoxytoluene, 4-methoxytoluene, 2,3-dimethylanisole, 2,4-dimethylanisole and the like.
  • ester solvents examples include aromatic esters such as phenyl acetate, phenyl propionate, methyl benzoate, ethyl benzoate, propyl benzoate, n-butyl benzoate and the like.
  • aromatic hydrocarbon solvents include toluene, xylene, cyclohexylbenzene, 3-isopropylbiphenyl, 1,2,3,4-tetramethylbenzene, 1,4-diisopropylbenzene, cyclohexylbenzene, methylnaphthalene and the like.
  • amide solvents examples include N, N-dimethylformamide, N, N-dimethylacetamide and the like. Besides these, dimethyl sulfoxide and the like can also be used.
  • the formation of the hole injection layer 3 by the wet film formation method usually prepares a composition for forming the hole injection layer, and then forms the layer on the layer corresponding to the lower layer of the hole injection layer 3 (usually, the anode 2).
  • the film is formed by coating and drying.
  • the hole injection layer 3 usually dries the coating film by heating, reduced-pressure drying, or the like after film formation.
  • the hole injection layer 3 When forming the hole injection layer 3 by a vacuum evaporation method, usually, one or two or more of the constituent materials of the hole injection layer 3 (the above-mentioned hole transportable compound, electron accepting compound, etc.) are vacuumed. Put in a crucible installed in the container (if using two or more types of materials, put each one in a separate crucible), evacuate the vacuum container to about 10 -4 Pa with a vacuum pump, and then heat the crucible And (if two or more materials are used, usually each crucible is heated) and evaporated while controlling the evaporation amount of the material in the crucible (when two or more materials are used, they are usually independent of each other) To control the amount of evaporation) to form a hole injection layer on the anode on the substrate placed facing the crucible. In addition, when using 2 or more types of materials, those mixtures can be put in a crucible, and it can also be heated and evaporated, and a positive hole injection layer can also be formed.
  • the degree of vacuum at the time of deposition is not limited, but usually 0.1 ⁇ 10 ⁇ 6 Torr (0.13 ⁇ 10 ⁇ 4 Pa) or more and 9.0 ⁇ 10 ⁇ 6 Torr (12.0 ⁇ 10 ⁇ 4 Pa) or less It is.
  • the deposition rate is not limited as long as the effect of the present invention is not significantly impaired, but is usually 0.1 ⁇ / sec or more and 5.0 ⁇ / sec or less.
  • the film formation temperature at the time of vapor deposition is not limited as long as the effects of the present invention are not significantly impaired, but it is preferably carried out at 10 ° C. or more and 50 ° C. or less.
  • the hole injection layer 3 may be crosslinked in the same manner as the hole transport layer 4 described later.
  • the hole transport layer 4 is a layer responsible for transporting holes from the anode 2 side to the light emitting layer 5 side.
  • the hole transport layer 4 is not an essential layer in the OLED device, but it is preferable to form this layer in order to enhance the function of transporting holes from the anode 2 to the light emitting layer 5.
  • the hole transport layer 4 is generally formed between the anode 2 and the light emitting layer 5.
  • the hole injection layer 3 described above it is formed between the hole injection layer 3 and the light emitting layer 5.
  • the film thickness of the hole transport layer 4 is usually 5 nm or more, preferably 10 nm or more, and on the other hand, is usually 300 nm or less, preferably 100 nm or less.
  • the method of forming the hole transport layer 4 may be vacuum evaporation or wet film formation. It is preferable to form by a wet film-forming method at the point which is excellent in the film-forming property. Although the formation method of a general hole transport layer is demonstrated below, it is preferable that a hole transport layer is formed by the wet-film-forming method.
  • the hole transport layer 4 usually contains a hole transport compound.
  • a hole transport compound As the hole transporting compound contained in the hole transporting layer 4, two or more tertiary amines represented by 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl are exemplified.
  • Aromatic diamines containing at least two fused aromatic rings substituted by nitrogen atoms JP-A-5-234681); 4,4 ′, 4 ′ ′-tris (1-naphthylphenylamino) triphenylamine and the like
  • Aromatic amine compounds having a starburst structure J. Lumin., Vol. 72-74, p.
  • Aromatic amine compounds consisting of tetramer of triphenylamine (Chem. Commun., P. 2175, 1996) Spiro compounds such as 2,2 ′, 7,7′-tetrakis- (diphenylamino) -9,9′-spirobifluorene (Synth. Metals, vol. 91, 2) 9, pp. 1997); 4,4'-N, N'carbazole derivatives such as di-biphenyl; and the like as preferred.
  • polyvinylcarbazole polyvinyltriphenylamine (JP-A-7-53953); polyarylene ether sulfone containing tetraphenylbenzidine (Polym. Adv. Tech., Volume 7, page 33, 1996), etc. Is also preferably used.
  • the above-mentioned hole injection layer is usually formed by a wet process except that a composition for forming a hole transport layer is used in place of the composition for forming a hole injection layer.
  • the hole transport layer can be formed in the same manner as the film method.
  • the composition for positive hole transport layer formation contains a solvent further.
  • the solvent used for the composition for forming a hole transport layer the same solvent as the solvent used for the composition for forming a hole injection layer described above can be used.
  • the concentration of the hole transportable compound in the composition for forming a hole transport layer can be in the same range as the concentration of the hole transportable compound in the composition for forming a hole injection layer.
  • the formation of the hole transport layer by the wet film formation method can be performed in the same manner as the above-described hole injection layer film formation method.
  • the above-mentioned materials of the hole transport layer are used instead of the material of the hole injection layer.
  • the hole transport layer can be formed in the same manner as in the case where the hole injection layer is formed by vacuum evaporation.
  • the film forming conditions such as the degree of vacuum at the time of vapor deposition, the vapor deposition rate, and the temperature can be formed under the same conditions as the vacuum vapor deposition of the hole injection layer.
  • the light emitting layer 5 is a layer having a function of emitting light by being excited by recombination of holes injected from the anode 2 and electrons injected from the cathode 9 when an electric field is applied between a pair of electrodes. .
  • the light emitting layer 5 is a layer formed between the anode 2 and the cathode 9, and the light emitting layer is formed between the hole injection layer and the cathode when there is a hole injection layer on the anode, If there is a hole transport layer on top, it is formed between the hole transport layer and the cathode.
  • the film thickness of the light emitting layer 5 is optional as long as the effects of the present invention are not significantly impaired, but a thicker one is preferable in that defects are not easily generated in the film, and a thinner one is preferable in that a low driving voltage is easily achieved. . Therefore, the thickness is preferably 3 nm or more, more preferably 5 nm or more, and on the other hand, usually 200 nm or less, and further preferably 100 nm or less.
  • the light emitting layer 5 contains at least a material having a property of light emission (light emitting material), and preferably, a material having a charge transporting property (charge transporting material).
  • the light emitting layer is formed of a composition for forming an OLED element, which contains the light emitting material and the charge transporting material described above.
  • known materials other than the light emitting material and the charge transporting material may be contained as long as the effects of the present invention are not impaired.
  • the method of forming the light emitting layer may be vacuum deposition or wet film formation, but the wet film formation is preferable because the film formability is excellent, and spin coating and inkjet are more preferable.
  • the light emitting layer is formed by a wet film formation method, the above-described holes are generally used except that the composition for forming an OLED element containing the light emitting material and the charge transport material is used instead of the composition for forming a hole injection layer.
  • a light emitting layer can be formed in the same manner as in the case of forming the injection layer by a wet film formation method.
  • the composition for forming an OLED element may contain a solvent.
  • the solvent include ether solvents, ester solvents, aromatic hydrocarbon solvents, and amide solvents listed for the formation of the hole injection layer, alkane solvents, halogenated aromatic hydrocarbon solvents, Aliphatic alcohol solvents, alicyclic alcohol solvents, aliphatic ketone solvents, alicyclic ketone solvents and the like can be mentioned.
  • alkane solvents alkane solvents, halogenated aromatic hydrocarbon solvents
  • Aliphatic alcohol solvents, alicyclic alcohol solvents, aliphatic ketone solvents, alicyclic ketone solvents and the like can be mentioned.
  • the specific example of a solvent is given to the following, it will not be limited to these, unless the effect of the present invention is spoiled.
  • aliphatic ether solvents such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol-1-monomethyl ether acetate (PGMEA); 1,2-dimethoxybenzene, 1,3-dimethoxybenzene, anisole, phenetole, 2
  • Aromatic ether solvents such as -methoxytoluene, 3-methoxytoluene, 4-methoxytoluene, 2,3-dimethylanisole, 2,4-dimethylanisole, diphenyl ether; phenyl acetate, phenyl propionate, methyl benzoate, benzoic acid
  • Aromatic ester solvents such as ethyl, propyl benzoate and n-butyl benzoate; toluene, xylene, mesitylene, cyclohexylbenzene, tetralin, 3-isopropylbiphenyl, 1,2,3,
  • the hole blocking layer 6 may be provided between the light emitting layer 5 and the electron injection layer 8 described later.
  • the hole blocking layer 6 is a layer stacked on the light emitting layer 5 so as to be in contact with the interface of the light emitting layer 5 on the cathode 9 side.
  • the hole blocking layer 6 has a role to block the transfer of holes transferred from the anode 2 to the cathode 9, and a role to efficiently transport electrons injected from the cathode 9 toward the light emitting layer 5.
  • the physical properties required for the material constituting the hole blocking layer 6 include high electron mobility and low hole mobility, large energy gap (difference between HOMO and LUMO), excited triplet level (T1) Is high.
  • the hole blocking layer As a material of the hole blocking layer satisfying such conditions, for example, bis (2-methyl-8-quinolinolato) (phenolato) aluminum, bis (2-methyl-8-quinolinolato) (triphenylsilanolato) aluminum etc.
  • Styryl compounds JP-A-11-242996; triazole derivatives such as 3- (4-biphenylyl) -4-phenyl-5- (4-tert-butylphenyl) -1,2,4-triazole 7-41759)); phenanthroline derivatives such as basokuproin (Japanese Patent Laid-Open No. 10-79297); It is. Furthermore, a compound having at least one pyridine ring substituted at the 2, 4, 6 position described in WO 2005/022962 is also preferable as a material of the hole blocking layer.
  • the hole blocking layer 6 There is no limitation on the method of forming the hole blocking layer 6. Therefore, it can be formed by a wet film formation method, a vapor deposition method, or another method.
  • the film thickness of the hole blocking layer 6 is arbitrary as long as the effects of the present invention are not significantly impaired, but is usually 0.3 nm or more, preferably 0.5 nm or more, and usually 100 nm or less, preferably 50 nm or less is there.
  • the electron transport layer 7 is provided between the light emitting layer 5 and the electron injection layer 8 for the purpose of further improving the current efficiency of the device.
  • the electron transport layer 7 is formed of a compound capable of efficiently transporting electrons injected from the cathode 9 in the direction of the light emitting layer 5 between electrodes to which an electric field is applied.
  • the electron transporting compound used for the electron transporting layer 7 has high electron injection efficiency from the cathode 9 or the electron injecting layer 8 and high electron mobility, and efficiently transports the injected electrons. It is necessary that the compound is capable of
  • the electron transporting compound used for the electron transporting layer include metal complexes such as aluminum complex of 8-hydroxyquinoline (JP-A-59-194393), 10-hydroxybenzo [h] quinoline Metal complexes, oxadiazole derivatives, distyrylbiphenyl derivatives, silole derivatives, 3-hydroxyflavone metal complexes, 5-hydroxyflavone metal complexes, benzoxazole metal complexes, benzothiazole metal complexes, trisbenzimidazolylbenzene (US Pat. No.
  • the film thickness of the electron transport layer 7 is usually 1 nm or more, preferably 5 nm or more, and usually 300 nm or less, preferably 100 nm or less.
  • the electron transport layer 7 is formed by laminating on the hole blocking layer 6 by a wet film formation method or a vacuum evaporation method in the same manner as described above. Usually, a vacuum evaporation method is used.
  • the electron injection layer 8 plays a role of efficiently injecting electrons injected from the cathode 9 into the electron transport layer 7 or the light emitting layer 5.
  • the material forming the electron injection layer 8 is preferably a metal having a low work function.
  • an alkali metal such as sodium or cesium, an alkaline earth metal such as barium or calcium, or the like is used.
  • the film thickness is usually preferably 0.1 nm or more and 5 nm or less.
  • an alkali metal such as sodium, potassium, cesium, lithium or rubidium is doped to an organic electron transport material represented by a nitrogen-containing heterocyclic compound such as bathophenanthroline or a metal complex such as an aluminum complex of 8-hydroxyquinoline ( JP-A-10-270171, JP-A-2002-100478, JP-A-2002-100482, etc.) can also improve the electron injection property and the electron transport property and make it possible to achieve both excellent film quality. It is preferable because
  • the film thickness of the electron injection layer 8 is usually 5 nm or more, preferably 10 nm or more, and usually 200 nm or less, preferably 100 nm or less.
  • the electron injection layer 8 is formed by laminating on the light emitting layer 5 or the hole blocking layer 6 or the electron transport layer 7 thereon by a wet film formation method or a vacuum evaporation method. The details of the wet film formation method are the same as those of the light emitting layer described above.
  • the cathode 9 plays a role of injecting electrons into a layer (electron injection layer, light emitting layer, etc.) adjacent to the light emitting layer 5 side of the cathode.
  • a layer electrostatic layer, electrostatic layer, etc.
  • metals having a low work function such as tin, magnesium, indium, calcium, Metals such as aluminum and silver or alloys thereof are preferably used.
  • the alloy include, for example, magnesium-silver alloy, magnesium-indium alloy, aluminum-lithium alloy and the like.
  • a metal layer having a high work function and stable to the atmosphere on the cathode to protect the cathode made of a low work function metal.
  • stack metals, such as aluminum, silver, copper, nickel, chromium, gold, platinum, are mentioned, for example.
  • the film thickness of the cathode is usually similar to that of the anode.
  • the structure of the OLED device is the reverse of the above-described structure, ie, a cathode, an electron injection layer, an electron transport layer, a hole blocking layer, a light emitting layer, a hole transport layer, a hole injection layer on the substrate. It is also possible to laminate in the order of the anode.
  • the OLED element 10 When the OLED element 10 is applied to an OLED light emitting device, it may be used as a single OLED element, may be used in a configuration in which a plurality of OLED elements are arranged in an array, and the anode and the cathode are XY You may use it as the structure arrange
  • Emitting wavelength of light emitting material and charge transport material The emission spectrum in toluene was measured at room temperature, and the wavelength of the maximum of the spectrum was taken as the emission wavelength value ( ⁇ em) of the light emitting material and the charge transporting material.
  • E gs1 , E gt1 , E hs1 , E ht1 E gs1 and E hs1 were the onset values of the emission spectrum in toluene at room temperature.
  • E gt1 and E ht1 were the onset values of the delayed emission spectrum (the delay time is 0.5 ms) in toluene at 77 K.
  • the twist between the donor part and the acceptor part of the compound was calculated using the obtained optimized structure of the S1 excited state, and the relationship with the measured value of ⁇ E st was investigated. The results are shown in FIG. From the results of FIG. 2, it can be understood that the twist between the donor part and the acceptor part of the compound (Twist) is correlated with ⁇ E st .
  • Example 1 As a substrate of the OLED element, an ITO film having a film thickness of 130 nm was formed as an anode on a glass substrate. The substrate was subjected to ultrasonic cleaning treatment in the following order: pure water, surfactant, pure water, acetone, and isopropanol. The cleaned substrate was blown dry with dry nitrogen and then subjected to oxygen plasma treatment. The substrate was introduced into a vacuum deposition chamber, and MoO 3 was deposited on the ITO film at a deposition rate of 0.2 ⁇ / sec to form a hole injection layer with a thickness of 15 nm.
  • a composition for a hole transport layer was prepared by dissolving 10 mg of the poly-tricarbazole compound shown below in 1 mL of dehydrated chlorobenzene. This composition was spin-coated on the hole injection layer in a glove box at a spinner rotation speed of 600 rpm for 60 seconds. The resultant was heated at 110 ° C. for 2 minutes on a hot plate to form a hole transport layer having a thickness of 73 nm.
  • the substrate is transferred to a vacuum deposition chamber, and a compound 20 shown below as a light emitting material and a compound 21 shown below as a charge transporting material are co-deposited on the hole transporting layer at a molar ratio of 25:75 A 25 nm-thick light emitting layer was formed.
  • 1,3,5-tri [3- (diphenylphosphoryl) phenyl] benzene shown below was vacuum deposited on the light emitting layer to form a hole blocking layer with a thickness of 4 nm.
  • LiF was vapor-deposited on the electron transport layer to form an electron injection layer with a thickness of 1 nm.
  • metal aluminum was vapor-deposited on the electron injection layer to form a cathode with a film thickness of 50 nm.
  • silver was vapor-deposited to a thickness of 100 nm to aid electrical contact to the cathode.
  • an OLED element according to Example 1 was produced.
  • Example 2 Using a light emitting layer with a film thickness of 25 nm obtained by co-evaporating Compound 20 as a light emitting material and Compound 22 as a charge transporting material at a molar ratio of 26:74 instead of the light emitting layer in Example 1 Similar to Example 1 except that a hole transport layer having a film thickness of 80 nm obtained by spin coating the composition for a hole transport layer at a rotation number of 500 rpm was used instead of the hole transport layer in Example 1. Then, the OLED element according to Example 2 was manufactured.
  • Example 3 Similar to Example 1 except that instead of the light emitting layer in Example 1, a light emitting layer with a film thickness of 25 nm was used, in which Compound 20 and Compound 23 as a charge transport material were co-deposited at a molar ratio of 30:70 as a light emitting material. Then, an OLED element according to Example 3 was produced.
  • Example 1 Hole transport in Example 1 using a light emitting layer with a film thickness of 25 nm codeposited with Compound 24 as a light emitting material and Compound 25 as a charge transport material at a molar ratio of 3:97 instead of the light emitting layer in Example 1
  • An OLED element according to Comparative Example 1 was produced in the same manner as in Example 1 except that a hole transport layer having a thickness of 65 nm was used as the layer, and the composition for a hole transport layer was spin coated at a rotational speed of 750 rpm. .
  • the excitation triplet energy (E gt1 ) of the compound 24 used for the light emitting material of Comparative Example 1 is the literature value of the excitation triplet energy of perylene which is its core skeleton ( J. Org. Chem ., 2014, vol. 79, The maximum value is 1.53 eV or less since page 2038) is 1.53 eV.
  • the value of ⁇ E st is the difference between the excited singlet energy (E gs1 ) 2.78 eV obtained from the rise of the emission spectrum at room temperature and the highest value of the excited triplet energy, and is 1.25 eV or more.
  • the excitation triplet energy (E ht1 ) of the compound 25 used for the charge transport material of Comparative Example 1 is the literature value of the excitation triplet energy of anthracene which is its core skeleton (Adv. Funct. Mater., 2013, Volume 23) , 739) is 1.85 eV, so the maximum value is 1.85 eV or less.
  • the value of ⁇ E st is the difference between the determined excitation singlet energy (E hs1 ) 3.11 eV of the emission spectrum at room temperature and the maximum value of this excitation triplet energy (E ht1 ), and is 1.26 eV or more is there.
  • the denominator of the parameter (E hs1 -E gs1 ) / (E hs1 -E ht1 ) in Comparative Example 1 corresponds to ⁇ E st of the compound 25 used for the charge transport material. Since ⁇ E st of the compound 25 is 1.26 eV or more, (E hs1 -E gs1 ) / (E hs1 -E ht1 ) is the difference between the singlet energies of the charge transport material and the light emitting material divided by 1.26 eV Or less.
  • (E hs1 -E gs1 ) / (E hs1 -E ht1 ) of compound 25 is calculated to be 0.26 or less, and the relationship (E hs1 -E gs1 ) / (E hs1 -E ht1 ) ⁇ 1. Do not meet one.

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Abstract

L'invention concerne une composition pour former un élément OLED, qui contient un matériau électroluminescent et un matériau de transport de charge, et dans lequel : à la fois le matériau électroluminescent et le matériau de transport de charge ont des propriétés TADF ; la valeur absolue ∆Est de la différence d'énergie entre l'énergie d'excitation de singulet et l'énergie d'excitation de triplet du matériau de transport de charge est de 0,37 eV ou moins ; et la différence entre la longueur d'onde de pic d'émission du matériau de transport de charge et la longueur d'onde de pic d'absorption du matériau électroluminescent, ladite longueur d'onde de pic d'absorption étant la longueur d'onde la plus longue parmi les longueurs d'onde de pic d'absorption de celui-ci, est de 95 nm ou moins.
PCT/JP2018/025274 2017-07-03 2018-07-03 Composition pour former un élément oled, et élément oled Ceased WO2019009307A1 (fr)

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WO2020189283A1 (fr) * 2019-03-18 2020-09-24 コニカミノルタ株式会社 Composé de transport de charge et son procédé de fabrication, composition d'encre, matériau d'élément électroluminescent organique, etc.
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CN110511177A (zh) * 2019-09-16 2019-11-29 南京邮电大学 一种d-a型tadf材料及其制备方法和应用
JP2021127325A (ja) * 2020-02-14 2021-09-02 三菱ケミカル株式会社 芳香族ジアミン誘導体
JP7463755B2 (ja) 2020-02-14 2024-04-09 三菱ケミカル株式会社 芳香族ジアミン誘導体
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WO2022196603A1 (fr) * 2021-03-16 2022-09-22 株式会社Kyulux Composition, utilisation de ladite composition comme composition électroluminescente, film, utilisation dudit film comme film électroluminescent, élément électroluminescent organique, procédé de conception de la composition et programme de mise en œuvre dudit procédé de conception
JP2022142304A (ja) * 2021-03-16 2022-09-30 株式会社Kyulux 組成物、その組成物の発光組成物としての使用、膜、その膜の発光膜としての使用、有機エレクトロルミネッセンス素子、組成物の設計方法およびその設計方法を実施するためのプログラム
JP7674727B2 (ja) 2021-03-16 2025-05-12 株式会社Kyulux 組成物、その組成物の発光組成物としての使用、膜、その膜の発光膜としての使用、有機エレクトロルミネッセンス素子、組成物の設計方法およびその設計方法を実施するためのプログラム

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