WO2021172452A1 - アリールアミン化合物およびそれを用いる電子機器 - Google Patents

アリールアミン化合物およびそれを用いる電子機器 Download PDF

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WO2021172452A1
WO2021172452A1 PCT/JP2021/007162 JP2021007162W WO2021172452A1 WO 2021172452 A1 WO2021172452 A1 WO 2021172452A1 JP 2021007162 W JP2021007162 W JP 2021007162W WO 2021172452 A1 WO2021172452 A1 WO 2021172452A1
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French (fr)
Japanese (ja)
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幸喜 加瀬
相原 高
丁浩 柳
峯香 李
淳一 泉田
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Hodogaya Chemical Co Ltd
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Hodogaya Chemical Co Ltd
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Priority to JP2022503707A priority Critical patent/JP7699099B2/ja
Priority to EP21760837.1A priority patent/EP4112613A1/en
Priority to US17/798,144 priority patent/US20230099897A1/en
Priority to KR1020227025883A priority patent/KR102931949B1/ko
Priority to CN202180014275.9A priority patent/CN117337283A/zh
Publication of WO2021172452A1 publication Critical patent/WO2021172452A1/ja
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    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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Definitions

  • the present invention relates to a compound and an element suitable for an organic electroluminescence element (hereinafter, abbreviated as an organic EL element) which is a self-luminous element suitable for various display devices. It relates to an organic EL device using a compound.
  • an organic electroluminescence element hereinafter, abbreviated as an organic EL element
  • the organic EL element is a self-luminous element, it is brighter and has better visibility than the liquid crystal element, and can display clearly, so that active research has been conducted.
  • Non-Patent Document 2 the use of triplet excitons has been attempted for the purpose of further improving the luminous efficiency, and the use of phosphorescent compounds has been studied (see, for example, Non-Patent Document 2).
  • devices that utilize thermally activated delayed fluorescence (TADF) have also been developed. Efficiency has been achieved (see, for example, Non-Patent Document 3).
  • the light emitting layer can also be prepared by doping a charge transporting compound generally called a host material with a fluorescent compound, a phosphorescent compound, or a material that emits delayed fluorescence.
  • a charge transporting compound generally called a host material
  • a fluorescent compound generally called a fluorescent compound
  • a phosphorescent compound or a material that emits delayed fluorescence.
  • the selection of an organic material in an organic EL device has a great influence on various properties such as efficiency and durability of the device (see, for example, Non-Patent Document 2).
  • the charges injected from both electrodes are recombined in the light emitting layer to obtain light emission, but it is important how efficiently both hole and electron charges are transferred to the light emitting layer. It is necessary to use an element with excellent carrier balance. Therefore, by using a material having the property of enhancing the hole injection property of supplying the holes injected from the anode to the light emitting layer and enhancing the electron blocking property of blocking the electrons injected from the cathode, the positive holes are positive in the light emitting layer. High emission efficiency can be obtained by improving the probability of recombination of holes and electrons, and further confining excitons generated in the light emitting layer. For that purpose, the role played by the hole transport material is important.
  • the hole transport material has high hole injection property, high hole mobility, high electron blocking property, and high electron durability. Is required.
  • the heat resistance and amorphous nature of the material are also important for the life of the device.
  • thermal decomposition occurs even at a low temperature due to the heat generated when the element is driven, and the material deteriorates.
  • the material used is required to have high heat resistance and good amorphous property.
  • Hole transport materials that have been used in organic EL devices so far include N, N'-diphenyl-N, N'-di ( ⁇ -naphthyl) benzidine (NPD) and various aromatic amine derivatives (for example).
  • NPD N, N'-diphenyl-N, N'-di ( ⁇ -naphthyl) benzidine
  • Patent Document 1 and Patent Document 2 various aromatic amine derivatives
  • Tg glass transition point
  • an arylamine compound having a substituted carbazole structure or a fluorenyl skeleton-containing heterocyclic structure has been proposed as a compound having improved properties such as heat resistance and hole injection (for example, Patent Documents). 4 and Patent Document 5), in the element using these compounds in the hole injection layer or the hole transport layer, although the heat resistance and the light emission efficiency have been improved, it cannot be said that they are sufficient yet, and further. Low drive voltage and high light emission efficiency are required.
  • An object of the present invention is that, as a material for a highly efficient and highly durable organic EL device, (1) it has excellent hole injection / transport performance, (2) it has electron blocking ability, and (3) it is in a thin film state. It is to provide a material for an organic EL element having high stability and (4) excellent durability.
  • an organic EL element having (1) high luminous efficiency and high power efficiency, (2) low luminous start voltage and practical driving voltage, and (3) long life.
  • an arylamine compound having a fluorenyl skeleton-containing heterocyclic structure is excellent in hole injection / transport ability, thin film stability and durability.
  • an arylamine compound in which a nitrogen atom is directly bonded to the heterocyclic group has been developed as a hole transport material, but by providing an arylene group between the heterocyclic group and the nitrogen atom, the energy gap is wide. It has become possible to develop materials and materials with high heat resistance, and the material properties have been dramatically improved.
  • the widening energy gap blocks electrons from the cathode side to suppress electron outflow, and confining them in the light emitting layer contributes to the improvement of luminous efficiency and power efficiency.
  • the improved luminous efficiency suppresses power consumption, making it possible to reduce the load inside the element, and the improved heat resistance of the material improves the stability of thinning, achieving a longer life than the conventional life. As a result, the present invention has been completed (see Patent Document 5).
  • the present invention is an arylamine compound having a fluorenyl skeleton-containing heterocyclic structure represented by the following general formula (A).
  • R 1 to R 11 may be the same or different from each other, and may have a hydrogen atom, a heavy hydrogen atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, and a substituent.
  • cycloalkyloxy groups substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups, substituted or unsubstituted condensed polycyclic aromatic groups, or substituted or unsubstituted aryl Represents an oxy group.
  • L represents a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a divalent group of a substituted or unsubstituted condensed polycyclic aromatic group.
  • n is 1 or 2, and when n is 2, L may be the same or different from each other.
  • Ar 1 and Ar 2 may be the same or different from each other, and may be a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, or a substituted or unsubstituted condensed polycyclic aromatic group.
  • X represents an oxygen atom, a sulfur atom, or a nitrogen atom having a substituent.
  • L and Ar 1 and Ar 1 and Ar 2 are linked to each other by being selected from a single bond or a substituted or unsubstituted methylene group, an oxygen atom, a sulfur atom, and a nitrogen atom having a substituent. It may be bonded to each other via a group to form a ring.
  • the present invention is based on the general formula (A).
  • the present invention is based on the general formula (A). It is an arylamine compound having a fluorenyl skeleton-containing heterocyclic structure according to 1) or 2) above, wherein X is an oxygen atom.
  • the present invention is based on the general formula (A).
  • the present invention is based on the general formula (A).
  • the organic layer has an aryl having a fluorenyl skeleton-containing heterocyclic structure according to any one of 1) to 5) above. It is an organic EL element containing an amine compound.
  • the present invention is the organic EL device according to 6) above, wherein the organic layer is an electron blocking layer.
  • the present invention is the organic EL device according to 6) above, wherein the organic layer is a hole transport layer.
  • the present invention is the organic EL device according to 6) above, wherein the organic layer is a hole injection layer.
  • the present invention is the organic EL device according to 6) above, wherein the organic layer is a light emitting layer.
  • the present invention relates to an electronic device using an electronic component having a pair of electrodes and at least one organic layer sandwiched between them, wherein the organic layer is described in any one of 1) to 5) above.
  • a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent and “having a substituent” represented by R 1 to R 11 in the general formula (A).
  • a cycloalkyl group having 5 to 10 carbon atoms which may be present or "a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent”
  • a substituent represented by R 1 to R 11 in the general formula (A).
  • a cycloalkyl group having 5 to 10 carbon atoms which may be present or "a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent”
  • 1 carbon atom number Specific examples of the “linear or branched alkyl group having 6 to 6", “cycloalkyl group having 5 to 10 carbon atoms” or “linear or branched alkenyl group having 2 to 6 carbon atoms” are specific.
  • a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent and “having a substituent” represented by R 1 to R 11 in the general formula (A).
  • a "substituent” in "a cycloalkyl group having 5 to 10 carbon atoms which may be present” or "a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent” Specifically, heavy hydrogen atom, cyano group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom, iodine atom; silyl group such as trimethylsilyl group, triphenylsilyl group; methyl group, ethyl group, propyl
  • a linear or branched alkyl group having 1 to 6 carbon atoms such as a group; a linear or branched alkyloxy group having 1 to 6 carbon atoms such as a methyloxy group, an ethy
  • a benzene ring substituted with these substituents, or a plurality of substituents substituted with the same benzene ring are single-bonded, or substituted or unsubstituted methylene groups, oxygen atoms, sulfur atoms, and substituents.
  • a ring may be formed by bonding with each other via a linking group selected from a nitrogen atom having a group.
  • the "substituent” in the “cycloalkyloxy group having 5 to 10 carbon atoms” may have a “substituent” represented by R 1 to R 11 in the general formula (A).
  • substituted alkenyl group having 2 to 6 carbon atoms can be mentioned, and the same can be mentioned as possible embodiments. ..
  • Substituted or unsubstituted aromatic hydrocarbon group "substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted aromatic heterocyclic group” represented by R 1 to R 11 in the general formula (A).
  • aromatic hydrocarbon group “aromatic heterocyclic group” or “condensed polycyclic aromatic group” in the "ring aromatic group” include a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group and an anthracenyl group.
  • aryloxy group in the "substituted or unsubstituted aryloxy group” represented by R 1 to R 11 in the general formula (A) include a phenyloxy group, a biphenylyloxy group, and a terpheni. Examples thereof include a aryloxy group, a naphthyloxy group, an anthrasenyloxy group, a phenylanthrenyloxy group, a fluorenyloxy group, an indenyloxy group, a pyrenyloxy group, and a peryleneyloxy group.
  • the "substituent” in the "substituted aryloxy group” represented by R 1 to R 11 in the general formula (A) is used.
  • the same as those shown as the "substituent” in the "linear or branched alkenyl group having 2 to 6 carbon atoms which may be possessed” can be mentioned, and the possible embodiments are also the same. Can be mentioned.
  • a hydrogen atom, a deuterium atom, or a substituted or unsubstituted phenyl group is preferable from the viewpoint of stability in a thin film state, and a hydrogen atom, a deuterium atom, or a deuterium atom or Unsubstituted phenyl groups are more preferred.
  • R 10 and R 11 in the general formula (A) a substituted or unsubstituted methyl group or a substituted or unsubstituted phenyl group is preferable from the viewpoint of the heat resistance of the compound, and the unsubstituted methyl group or the unsubstituted phenyl group is preferable. Phenyl group is more preferred. Further, it is preferable that R 10 and R 11 are the same.
  • Substituted or unsubstituted aromatic hydrocarbon group "substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted condensed polycyclic aromatic group” represented by L in the general formula (A).
  • aromatic hydrocarbon group "aromatic heterocyclic group” or “condensed polycyclic aromatic group” in the above, "substituted or unsubstituted” represented by R 1 to R 11 in the general formula (A).
  • the "substituent” in the "substituted aromatic hydrocarbon group", “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic group” represented by L in the general formula (A) is a general formula ( In A), "a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent” and “even if it has a substituent” represented by R 1 to R 11 in the above. What is shown as a “substituent” in "a good cycloalkyl group having 5 to 10 carbon atoms” or "a linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent". Similar ones can be mentioned, and the same ones can be mentioned as possible embodiments.
  • a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group is preferable from the viewpoint of hole transportability and electron blocking ability.
  • An unsubstituted phenylene group, an unsubstituted biphenylene group, or an unsubstituted naphthylene group is more preferable, and an unsubstituted phenylene group or an unsubstituted naphthylene group is particularly preferable.
  • n in the general formula (A) is preferably 1.
  • Substituted or unsubstituted aromatic hydrocarbon group "substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted aromatic heterocyclic group” represented by Ar 1 and Ar 2 in the general formula (A).
  • the "aromatic hydrocarbon group”, “aromatic heterocyclic group” or “condensed polycyclic aromatic group” in the “ring aromatic group” is represented by “ R 1 to R 11" in the general formula (A).
  • Aromamatic hydrocarbon group in “substituted or unsubstituted aromatic hydrocarbon group", “substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted condensed polycyclic aromatic group” The same as those shown as “heterocyclic group” or “condensed polycyclic aromatic group” can be mentioned.
  • an unsubstituted phenyl group or an unsubstituted biphenylyl group is preferable from the viewpoint of hole transporting property and electron blocking ability.
  • X in the general formula (A) is preferably an oxygen atom from the viewpoint of hole transportability and electron blocking ability.
  • the arylamine compound having a fluorenyl skeleton-containing heterocyclic structure represented by the general formula (A), which is preferably used for the organic EL device of the present invention, is a hole injection layer, a hole transport layer, and an electron of the organic EL device. It is preferably used as a constituent material of a blocking layer or a light emitting layer, and more preferably used as a constituent material of a hole transporting layer or an electron blocking layer.
  • the arylamine compound having a fluorenyl skeleton-containing heterocyclic structure of the present invention has (1) better hole injection characteristics, (2) higher hole mobility, and (3) electrons than conventional hole transport materials. It has characteristics such as excellent blocking ability, (4) high electron resistance, (5) stable presence in a thin film state, and (6) excellent heat resistance, and is a fluorenyl skeleton-containing heterocycle of the present invention.
  • an arylamine compound having a structure in an organic EL element (7) high light emission efficiency, (8) low light emission start voltage, (9) low practical drive voltage, (10) long life, etc. The characteristics are obtained.
  • the arylamine compound having a fluorenyl skeleton-containing heterocyclic structure of the present invention is excellent in hole injection / transport performance, thin film stability and durability.
  • the organic EL device having a hole injection layer and / or a hole transport layer produced by using the same compound as a hole injection material and / or a hole transport material has a hole transport efficiency to the luminous layer. It is possible to improve the durability of the element by improving the light emission efficiency and lowering the drive voltage, and to obtain the characteristics of high efficiency, low drive voltage, and long life.
  • the arylamine compound having a fluorenyl skeleton-containing heterocyclic structure of the present invention has excellent electron blocking ability, high electron resistance, is stable even in a thin film state, and has the characteristics of confining excitons generated in the light emitting layer. ..
  • the organic EL element having an electron blocking layer manufactured by using the compound as an electron blocking material has a high emission efficiency because the probability of recombination of holes and electrons is improved and heat deactivation is suppressed.
  • the maximum emission brightness is improved by lowering the drive voltage and improving the current immunity.
  • the arylamine compound having a fluorenyl skeleton-containing heterocyclic structure of the present invention has excellent hole transport properties and a wide bandgap.
  • the organic EL element having a light emitting layer produced by using the same compound as a host material is driven by forming a light emitting layer by supporting a fluorescent light emitter, a phosphorescent light emitting body, and a delayed fluorescent light emitting body called a dopant. The voltage is lowered and the luminous efficiency is improved.
  • the arylamine compound having a fluorenyl skeleton-containing heterocyclic structure of the present invention is useful as a material for a hole injection layer, a hole transport layer, an electron blocking layer or a light emitting layer of an organic EL device, and is a conventional organic EL device.
  • the light emission efficiency, drive voltage, and durability of the device can be improved.
  • the arylamine compound having a fluorenyl skeleton-containing heterocyclic structure of the present invention is a novel compound, but these compounds can be synthesized according to a method known per se (see, for example, Patent Document 5).
  • arylamine compounds having a fluorenyl skeleton-containing heterocyclic structure represented by the general formula (A), which are preferably used for the organic EL element of the present invention specific examples of the preferable compounds are shown in FIGS. 1 to 8. However, it is not limited to these compounds.
  • Purification of the arylamine compound having a fluorenyl skeleton-containing heterocyclic structure represented by the general formula (A) includes purification by column chromatography, adsorption purification with silica gel, activated charcoal, active clay, etc., recrystallization and crystallization method with a solvent. It can be carried out by a known method such as a sublimation purification method. Compound identification can be performed by NMR analysis. Examples of physical property values include measurement of melting point, glass transition point (Tg) and work function. The melting point is an index of vapor deposition, the glass transition point (Tg) is an index of stability in the thin film state, and the work function is an index of hole injection, hole transport, or electron blocking. Is.
  • the melting point and the glass transition point (Tg) can be measured by, for example, a high-sensitivity differential scanning calorimeter (DSC3100SA, manufactured by Bruker AXS) using powder.
  • DSC3100SA high-sensitivity differential scanning calorimeter
  • the work function can be obtained, for example, by forming a thin film of 100 nm on an ITO substrate and using an ionization potential measuring device (PYS-202, manufactured by Sumitomo Heavy Industries, Ltd.).
  • the structure of the organic EL element of the present invention is sequentially composed of an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and a cathode on a substrate, and a hole transport.
  • Examples thereof include those having an electron blocking layer between the light emitting layer and the light emitting layer, and those having a hole blocking layer between the light emitting layer and the electron transporting layer.
  • one organic layer can also serve as several layers.
  • one organic layer may also serve as a hole injection layer and a hole transport layer, and electrons. It is also possible to have a configuration in which the injection layer and the electron transport layer are combined.
  • an electrode material having a large work function such as ITO or gold is used.
  • the material of the hole injection layer of the organic EL element of the present invention it has a porphyrin compound typified by copper phthalocyanine, a starburst type triphenylamine derivative, and two or more triphenylamine structures or carbazolyl structures in the molecule.
  • An arylamine compound having a structure in which each is linked by a divalent group containing no single bond or a hetero atom, an accepting heterocyclic compound such as hexacyanoazatriphenylene, and a coating type polymer material can be used.
  • N, N'-diphenyl-N, N'- Di (m-tolyl) -benzidine hereinafter abbreviated as TPD
  • NPD N, N'-diphenyl-N, N'-di ( ⁇ -naphthyl) -benzidine
  • NPD N, N, Benzidine derivatives such as N', N'-tetrabiphenylylbenzidine, 1,1-bis [(di-4-tolylamino) phenyl] cyclohexane (hereinafter abbreviated as TAPC), and triphenylamine structure or carbazolyl in the molecule.
  • TPD N, N'-diphenyl-N, N'- Di (m-tolyl) -benzidine
  • NPD N, N'-diphenyl-N, N'-di ( ⁇ -naphthyl) -benzidine
  • TAPC 1,1-bis [(di-4-tolylamino) phen
  • Arylamine compounds having two or more structures, each of which has a structure linked by a divalent group that does not contain a single bond or a hetero atom, or the like can be used. These materials may be formed as a single layer, or a plurality of types may be mixed and formed, and each of them can be used as a single layer.
  • PEDOT poly (3,4-ethylenedioxythiophene)
  • PSS poly (styrene sulfonate)
  • a coating type polymer material can be used.
  • the hole injection layer or the hole transport layer is P-doped with a material usually used for these layers, such as trisbromophenylamine hexachloroantimony and a radialene derivative (see, for example, Patent Document 6).
  • a material usually used for these layers such as trisbromophenylamine hexachloroantimony and a radialene derivative (see, for example, Patent Document 6).
  • a polymer compound having the structure of a benzidine derivative such as TPD in its partial structure can be used.
  • TCTA 4,4', 4''-tri (N-carbazolyl) tri (N-carbazolyl) tri Phenylamine
  • TCTA 9,9-bis [4- (carbazole-9-yl) phenyl] fluorene, 1,3-bis (carbazole-9-yl) benzene
  • Ad-Cz 2,2-Bis (4-carbazole-9-ylphenyl) adamantan
  • the material of the light emitting layer of the organic EL element of the present invention in addition to the arylamine compound having a fluorenyl skeleton-containing heterocyclic structure of the present invention, metal complexes of quinolinol derivatives such as Alq 3 and various metal complexes, Anthracene derivatives, bisstyrylbenzene derivatives, pyrene derivatives, oxazole derivatives, polyparaphenylene vinylene derivatives and the like can be used.
  • the light emitting layer may be composed of a host material and a dopant material, and an anthracene derivative is preferably used as the host material.
  • an indole ring is condensed.
  • a heterocyclic compound having a partial structure of the ring a heterocyclic compound having a carbazole ring as a partial structure of the fused ring, a carbazole derivative, a thiazole derivative, a benzimidazole derivative, a polydialkylfluorene derivative and the like can be used.
  • the dopant material quinacridone, coumarin, rubrene, perylene and derivatives thereof, benzopyran derivative, rhodamine derivative, aminostyryl derivative and the like can be used.
  • a phosphorescent light emitter As the phosphorescent body, a phosphorescent body of a metal complex such as iridium or platinum can be used. For example, a green phosphorescent body such as Ir (ppy) 3 , a blue phosphorescent body such as Firpic and Fir6, and a red phosphorescent body such as Btp 2 Ir (acac) can be mentioned, and the host at this time can be mentioned.
  • the material as a hole injecting / transporting host material, in addition to 4,4'-di (N-carbazolyl) biphenyl (hereinafter abbreviated as CBP), carbazole derivatives such as TCTA and mCP, and the like, the present invention Arylamine compounds can be mentioned, and as electron-transporting host materials, p-bis (triphenylsilyl) benzene (hereinafter abbreviated as UGH2) and 2,2', 2''-(1,3,5) -Phenylene) -Tris (1-phenyl-1H-benzimidazole) (hereinafter abbreviated as TPBI) and the like can be mentioned.
  • UGH2 triphenylsilyl
  • TPBI 2,2', 2''-(1,3,5) -Phenylene) -Tris (1-phenyl-1H-benzimidazole)
  • the phosphorescent luminescent material it is preferable to dope the phosphorescent luminescent material to the host material by co-evaporation in the range of 1 to 30% by weight with respect to the entire light emitting layer in order to avoid concentration quenching.
  • the light emitting material it is also possible to use a material that emits delayed fluorescence such as a CDCB derivative such as PIC-TRZ, CC2TA, PXZ-TRZ, 4CzIPN (see, for example, Non-Patent Document 3).
  • a material that emits delayed fluorescence such as a CDCB derivative such as PIC-TRZ, CC2TA, PXZ-TRZ, 4CzIPN (see, for example, Non-Patent Document 3).
  • a phenanthroline derivative such as basokproin (hereinafter abbreviated as BCP)
  • BCP basokproin
  • a metal complex of a quinolinol derivative such as BAlq
  • various rare earth complexes such as a quinolinol derivative
  • an oxazole derivative such as BAlq
  • various rare earth complexes such as a compound having a hole blocking action
  • an oxazole derivative such as a triazole derivative
  • a triazine a compound having a hole blocking action
  • These materials may also serve as materials for the electron transport layer.
  • metal complexes of quinolinol derivatives such as Alq 3 and BAlq, various metal complexes, triazole derivatives, triazine derivatives, oxadiazole derivatives, pyridine derivatives, pyrimidine derivatives, benz Imidazole derivatives, thiadiazol derivatives, anthracene derivatives, carbodiimide derivatives, quinoxalin derivatives, pyridoindole derivatives, phenanthroline derivatives, silol derivatives and the like can be used.
  • an alkali metal salt such as lithium fluoride and cesium fluoride
  • an alkaline earth metal salt such as magnesium fluoride
  • a metal complex of a quinolinol derivative such as lithium quinolinol
  • aluminum oxide Metal oxides such as ytterbium (Yb), samarium (Sm), calcium (Ca), strontium (Sr) and cesium (Cs) can be used.
  • the electron injection layer can be omitted depending on the preferred selection of electron transport layer and cathode.
  • the electron injection layer and the electron transport layer materials usually used for these layers can be N-doped with a metal such as cesium.
  • a metal having a low work function such as aluminum and an alloy having a lower work function such as a magnesium silver alloy, a magnesium indium alloy, and an aluminum magnesium alloy are used as electrode materials. ..
  • each layer constituting the organic EL element can be formed into a thin film by a known method such as a vapor deposition method, a spin coating method and an inkjet method. Further, these materials may be formed as a single layer, or may be formed by mixing a plurality of types, and each of them can be used as a single layer.
  • Example 10 The melting point and glass transition point of the arylamine compound having a fluorenyl skeleton-containing heterocyclic structure obtained in the above example were measured by a high-sensitivity differential scanning calorimeter (DSC3100SA, manufactured by Bruker AXS). The results are shown in Table 1.
  • the arylamine compound having a fluorenyl skeleton-containing heterocyclic structure represented by the general formula (A) has a glass transition point of 120 ° C. or higher, indicating that the thin film state is stable. be.
  • Example 11 Using the arylamine compound having a fluorenyl skeleton-containing heterocyclic structure obtained in the above example, a thin-film deposition film having a thickness of 100 nm was prepared on an ITO substrate, and an ionization potential measuring device (manufactured by Sumitomo Heavy Industries, Ltd.) The work function was measured by PYS-202). The results are shown in Table 2.
  • the arylamine compound having a fluorenyl skeleton-containing heterocyclic structure represented by the general formula (A) is compared with the work function of 5.4 eV possessed by general hole transport materials such as NPD and TPD. Therefore, it has a higher work function value, shows a suitable energy level, and has a good hole transport capacity.
  • the organic EL element has a hole injection layer 3, a hole transport layer 4, and electrons on a glass substrate 1 on which a reflective ITO electrode is formed as a transparent anode 2 in advance, as in the organic EL element configuration shown in FIG.
  • the blocking layer 5, the light emitting layer 6, the electron transport layer 7, the electron injection layer 8, the cathode 9, and the capping layer 10 were vapor-deposited in this order.
  • a glass substrate 1 having an ITO having a film thickness of 50 nm, a silver alloy reflective film having a film thickness of 100 nm, and an ITO having a film thickness of 5 nm formed in this order was ultrasonically cleaned in isopropyl alcohol for 20 minutes.
  • a compound (HTM-1) having the following structural formula was formed as the hole transport layer 4 on the hole injection layer 3 so as to have a film thickness of 140 nm.
  • the compound (12) obtained in Example 1 was formed as an electron blocking layer 5 on the hole transport layer 4 so as to have a film thickness of 5 nm.
  • a compound (EMD-1) having the following structural formula and a compound (EMH-1) having the following structural formula are used as the light emitting layer 6, and the vapor deposition rate ratio is compound (EMD-1): EMH-1.
  • a compound (ETM-1) having the following structural formula and a compound (ETM-2) having the following structural formula are used as the electron transport layer 7, and the vapor deposition rate ratio is compound (ETM-1) :( ETM-. 2)
  • Two-way vapor deposition was performed at a vapor deposition rate of 50:50, and the film was formed so as to have a film thickness of 30 nm.
  • Lithium fluoride was formed on the electron transport layer 7 as an electron injection layer 8 so as to have a film thickness of 1 nm.
  • a magnesium-silver alloy was formed on the electron injection layer 8 as a cathode 9 so as to have a film thickness of 12 nm.
  • CPL-1 having the following structure was formed as the capping layer 10 so as to have a film thickness of 60 nm.
  • Table 3 summarizes the measurement results of the light emission characteristics when a DC voltage is applied to the organic EL device produced in Example 12 in the air at room temperature.
  • Example 13 In Example 12, the organic EL device under the same conditions except that the compound (14) obtained in Example 2 was used instead of the compound (12) obtained in Example 1 as the material of the electron blocking layer 5. was produced. Table 3 summarizes the measurement results of the light emission characteristics when a DC voltage is applied to the organic EL element manufactured under the same measurement conditions in the air and at room temperature.
  • Example 14 In Example 12, the organic EL device under the same conditions except that the compound (52) obtained in Example 3 was used instead of the compound (12) obtained in Example 1 as the material of the electron blocking layer 5. was produced. Table 3 summarizes the measurement results of the light emission characteristics when a DC voltage is applied to the organic EL element manufactured under the same measurement conditions in the air and at room temperature.
  • Example 15 In Example 12, the organic EL device under the same conditions except that the compound (7) obtained in Example 4 was used instead of the compound (12) obtained in Example 1 as the material of the electron blocking layer 5. was produced. Table 3 summarizes the measurement results of the light emission characteristics when a DC voltage is applied to the organic EL element manufactured under the same measurement conditions in the air and at room temperature.
  • Example 16 In Example 12, the organic EL device under the same conditions except that the compound (24) obtained in Example 5 was used instead of the compound (12) obtained in Example 1 as the material of the electron blocking layer 5. was produced. Table 3 summarizes the measurement results of the light emission characteristics when a DC voltage is applied to the organic EL element manufactured under the same measurement conditions in the air and at room temperature.
  • Example 17 In Example 12, the organic EL device under the same conditions except that the compound (26) obtained in Example 6 was used instead of the compound (12) obtained in Example 1 as the material of the electron blocking layer 5. was produced. Table 3 summarizes the measurement results of the light emission characteristics when a DC voltage is applied to the organic EL element manufactured under the same measurement conditions in the air and at room temperature.
  • Example 18 In Example 12, the organic EL device under the same conditions except that the compound (43) obtained in Example 7 was used instead of the compound (12) obtained in Example 1 as the material of the electron blocking layer 5. was produced. Table 3 summarizes the measurement results of the light emission characteristics when a DC voltage is applied to the organic EL element manufactured under the same measurement conditions in the air and at room temperature.
  • Example 19 In Example 12, the organic EL device under the same conditions except that the compound (61) obtained in Example 8 was used instead of the compound (12) obtained in Example 1 as the material of the electron blocking layer 5. was produced. Table 3 summarizes the measurement results of the light emission characteristics when a DC voltage is applied to the organic EL element manufactured under the same measurement conditions in the air and at room temperature.
  • Example 20 In Example 12, the organic EL device under the same conditions except that the compound (94) obtained in Example 9 was used instead of the compound (12) obtained in Example 1 as the material of the electron blocking layer 5. was produced. Table 3 summarizes the measurement results of the light emission characteristics when a DC voltage is applied to the organic EL element manufactured under the same measurement conditions in the air and at room temperature.
  • Example 12 As the material of the electron blocking layer 5, instead of the compound (12) obtained in Example 1, a compound having the following structural formula (HTM-2) (see, for example, Patent Document 5).
  • An organic EL device was produced under the same conditions except that the above was used.
  • Table 3 summarizes the measurement results of the light emission characteristics when a DC voltage is applied to the organic EL element manufactured under the same measurement conditions in the air and at room temperature.
  • Example 12 As the material of the electron blocking layer 5, instead of the compound (12) obtained in Example 1, a compound having the following structural formula (HTM-3) (see, for example, Patent Document 5).
  • HTM-3 a compound having the following structural formula (HTM-3) (see, for example, Patent Document 5).
  • An organic EL device was produced under the same conditions except that the above was used.
  • Table 3 summarizes the measurement results of the light emission characteristics when a DC voltage is applied to the organic EL element manufactured under the same measurement conditions in the air and at room temperature.
  • the device life measured is such that the emission brightness is 950 cd when the constant current drive is performed with the emission brightness (initial brightness) at the start of light emission set to 1000 cd / m 2. It was measured as the time until it attenuated to / m 2 (corresponding to 95% when the initial brightness was 100%: 95% attenuation).
  • the luminous efficiency when a current with a current density of 10 mA / cm 2 was passed was 7.98 to 8.28 cd / A of the organic EL elements of Comparative Examples 1 and 2, and the light emission efficiency of Examples 12 to 12.
  • the efficiency was 8.52 to 11.27 cd / A, which was high.
  • the organic EL elements of Comparative Examples 1 and 2 have a high power efficiency of 7.03 to 7.29 lm / W, whereas the organic EL elements of Examples 12 to 20 have a high power efficiency of 7.50 to 10.14 lm / W. It was efficient.
  • the element life (95% attenuation) is extended to 349 to 791 hours for the organic EL elements of Examples 12 to 20 as opposed to 298 to 327 hours for the organic EL elements of Comparative Examples 1 and 2. I understand.
  • the organic EL element using the arylamine compound having a fluorenyl skeleton-containing heterocyclic structure of the present invention has a large hole mobility and an excellent electron blocking ability. It was found that an organic EL element having high light emission efficiency and a long life can be realized as compared with the conventional organic EL element.
  • the organic EL device using the arylamine compound having a fluorenyl skeleton-containing heterocyclic structure of the present invention can improve the luminous efficiency and the durability of the organic EL device. Can be expanded to applications.
  • the arylamine compound having a fluorenyl skeleton-containing heterocyclic structure of the present invention is used not only for organic EL devices but also for electronic devices in fields such as electrophotographic photosensitive members, image sensors, photoelectric conversion devices, and solar cells. can do.

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