WO2021149773A1 - 有機エレクトロルミネッセンス素子 - Google Patents

有機エレクトロルミネッセンス素子 Download PDF

Info

Publication number
WO2021149773A1
WO2021149773A1 PCT/JP2021/002068 JP2021002068W WO2021149773A1 WO 2021149773 A1 WO2021149773 A1 WO 2021149773A1 JP 2021002068 W JP2021002068 W JP 2021002068W WO 2021149773 A1 WO2021149773 A1 WO 2021149773A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
substituted
substituent
general formula
unsubstituted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2021/002068
Other languages
English (en)
French (fr)
Japanese (ja)
Inventor
淳一 泉田
剛史 山本
幸喜 加瀬
駿河　和行
秀一 林
スンウク チャ
ソンフン ジュ
ビョンソン ヤン
ジファン キム
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hodogaya Chemical Co Ltd
SFC Co Ltd
Original Assignee
Hodogaya Chemical Co Ltd
SFC Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hodogaya Chemical Co Ltd, SFC Co Ltd filed Critical Hodogaya Chemical Co Ltd
Priority to KR1020227024229A priority Critical patent/KR102876616B1/ko
Priority to CN202180010435.2A priority patent/CN114981991A/zh
Priority to JP2021572796A priority patent/JP7498727B2/ja
Priority to EP21744719.2A priority patent/EP4095216A4/en
Priority to US17/792,001 priority patent/US20230101400A1/en
Publication of WO2021149773A1 publication Critical patent/WO2021149773A1/ja
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Images

Classifications

    • 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 materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H10K50/156—Hole transporting layers comprising a multilayered structure
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/658—Organoboranes

Definitions

  • the present invention relates to an organic electroluminescence element which is a self-luminous element suitable for various display devices, and more particularly, an organic electroluminescence element using a specific arylamine compound (hereinafter, abbreviated as an organic EL element). It is about.
  • organic EL elements are self-luminous elements, they are brighter and have better visibility than liquid crystal elements, and can display clearly, so active research has been conducted.
  • Non-Patent Document 3 Devices that utilize thermally activated delayed fluorescence (TADF) emission have also been developed.
  • TADF thermally activated delayed fluorescence
  • 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 with a fluorescent compound, a phosphorescent compound, or a material that emits delayed fluorescence.
  • 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.
  • the hole injection property and the electron blocking property that blocks the electrons injected from the cathode the probability of recombination of holes and electrons is improved, and excitons generated in the light emitting layer are generated. High emission efficiency can be obtained by confining. Therefore, the role played by the hole transport material is important, and a hole transport material having high hole injection property, high hole mobility, high electron blocking property, and high electron durability is required. ing.
  • 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.
  • NPD N, N'-diphenyl-N, N'-di ( ⁇ -naphthyl) benzidine
  • various aromatic amine derivatives are known.
  • NPD has a good hole transporting ability
  • the glass transition point (Tg) which is an index of heat resistance
  • Tg glass transition point
  • device characteristics deteriorate due to crystallization (for example).
  • Patent Document 4 the aromatic amine derivatives described in the above patent documents, compounds having an excellent mobility of holes of 10 -3 cm 2 / Vs or more are known (for example, Patent Documents).
  • Patent Document 2 because the electron blocking property is insufficient, some of the electrons pass through the light emitting layer, and improvement in light emitting efficiency cannot be expected. There has been a demand for a material having high properties, a thin film more stable, and high heat resistance. Further, although there is a report of a highly durable aromatic amine derivative (see, for example, Patent Document 3), it was used as a charge transport material used in an electrophotographic photosensitive member, and there was no example of using it as an organic EL element. ..
  • Arylamine compounds having a substituted carbazole structure have been proposed as compounds having improved properties such as heat resistance and hole injection (see, for example, Patent Documents 4 and 5), and these compounds are injected into holes.
  • the elements used for the layer or the hole transport layer have been improved in heat resistance and light emission efficiency, they are not yet sufficient, and further lower drive voltage and higher light emission efficiency are required. ..
  • An object of the present invention is as a material for an organic EL element having high efficiency and high durability, for an organic EL element having excellent hole injection / transport performance, electron blocking ability, stability in a thin film state, and durability. Materials are provided, and various materials for organic EL devices, which are excellent in hole and electron injection / transport performance, electron blocking ability, stability in a thin film state, and durability, are provided. It is an object of the present invention to provide an organic EL element having high efficiency, low drive voltage, and long life by combining them so that the characteristics of the above can be effectively exhibited.
  • the physical properties that the organic compound to be provided by the present invention should have are (1) good hole injection characteristics, (2) high hole mobility, and (3) thin film state. It can be mentioned that it is stable and (4) it has excellent heat resistance. Further, the physical characteristics that the organic EL element to be provided by the present invention should have are (1) high luminous efficiency and high power efficiency, (2) low luminous start voltage, and (3) practical drive. It can be mentioned that the voltage is low and (4) it has a long life.
  • an arylamine compound having a specific structure is excellent in hole injection / transport ability, thin film stability and durability, and variously.
  • the arylamine compound of the above was selected to prepare an organic EL device, and the characteristics of the device were evaluated diligently.
  • the present inventors have found that when an arylamine compound having a specific structure is selected as a material for the hole transport layer, holes injected from the anode side can be efficiently transported. Further, various organic EL devices combining light emitting materials having a specific structure and the like were produced, and the characteristics of the devices were evaluated diligently. As a result, the present invention has been completed.
  • the organic EL element of the present invention capable of solving the above problems is Equipped with anode and cathode, Between the anode and the cathode, at least a first hole transport layer, a second hole transport layer, a blue light emitting layer, and an electron transport layer are provided in this order from the anode side. At least one layer of the layers arranged between the first hole transport layer and the electron transport layer contains an arylamine compound represented by the following general formula (1). It is an organic electroluminescence element. (In the formula, Ar 1 , Ar 2 , Ar 3 and Ar 4 may be the same or different from each other, with substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups or substituted or absent.
  • L 1 represents a divalent group of a substituted or unsubstituted aromatic hydrocarbon, a divalent group of a substituted or unsubstituted aromatic heterocycle, and a divalent group of a substituted or unsubstituted fused polycyclic aromatic.
  • R 1 , R 2 and R 3 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.
  • n represents an integer of 1 to 3.
  • the arylamine compound represented by the general formula (1) which is preferably used for the organic EL device of the present invention, can be used as a constituent material of the hole transport layer of the organic EL device.
  • the arylamine compound represented by the general formula (1) has (1) good hole injection characteristics, (2) high hole mobility, (3) excellent electron blocking ability, and (4). ) It has the characteristics that the thin film state is stable and (5) it has excellent heat resistance.
  • the organic EL device of the present invention has higher hole mobility than conventional hole transport materials, has excellent electron blocking ability, has excellent amorphous properties, and has a stable thin film state. Since a compound is used, it is possible to realize an organic EL device having high efficiency, low drive voltage, and long life.
  • the hole transport layer has a two-layer structure of a first hole transport layer and a second hole transport layer, and the second hole transport layer located on the side adjacent to the light emitting layer is the general.
  • the arylamine compound represented by the general formula (1) it is a figure which shows the structural formula of the compound 1-1 to 1-15. As an example of the arylamine compound represented by the general formula (1), it is a figure which shows the structural formula of the compound 1-16 to 1-30. As an example of the arylamine compound represented by the general formula (1), it is a figure which shows the structural formula of the compound 1-31 to 1-45. As an example of the arylamine compound represented by the general formula (1), it is a figure which shows the structural formula of the compound 1-46 to 1-60. As an example of the arylamine compound represented by the general formula (1), it is a figure which shows the structural formula of the compound 1-61 to 1-75.
  • the arylamine compound represented by the general formula (1) it is a figure which shows the structural formula of the compound 1-76 to 1-90. As an example of the arylamine compound represented by the general formula (1), it is a figure which shows the structural formula of the compound 1-91 to 1-105. As an example of the arylamine compound represented by the general formula (1), it is a figure which shows the structural formula of the compound 1-106 to 1-120. As an example of the arylamine compound represented by the general formula (1), it is a figure which shows the structural formula of the compound 1-121 to 1-135. As an example of the arylamine compound represented by the general formula (1), it is a figure which shows the structural formula of the compound 1-136 to 1-150.
  • the arylamine compound represented by the general formula (1) it is a figure which shows the structural formula of the compound 1-151 to 1-165.
  • the arylamine compound represented by the general formula (1) it is a figure which shows the structural formula of the compound 1-166 to 1-178.
  • the compound represented by the general formula (2) it is a figure which shows the structure of the compound 2-1 to 2-15.
  • the compound represented by the general formula (2) it is a figure which shows the structural formula of the compound 2-16 to 2-24.
  • the compound represented by the general formula (3) it is a figure which shows the structure of the compound 3-1 to 3-6. It is a figure which showed the organic EL element composition of Examples 16-27, and Comparative Examples 1-2.
  • At least a first hole transport layer, a second hole transport layer, a blue light emitting layer, and an electron transport layer are provided in this order from the anode side.
  • At least one layer of the layers arranged between the first hole transport layer and the electron transport layer contains an arylamine compound represented by the following general formula (1).
  • Organic electroluminescence element In the formula, Ar 1 , Ar 2 , Ar 3 and Ar 4 may be the same or different from each other, with substituted or unsubstituted aromatic hydrocarbon groups, substituted or unsubstituted aromatic heterocyclic groups or substituted or absent.
  • L 1 represents a divalent group of a substituted or unsubstituted aromatic hydrocarbon, a divalent group of a substituted or unsubstituted aromatic heterocycle, and a divalent group of a substituted or unsubstituted fused polycyclic aromatic.
  • R 1 , R 2 and R 3 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.
  • n represents an integer of 1 to 3.
  • At least one layer of the layers arranged between the first hole transport layer and the blue light emitting layer contains the arylamine compound represented by the general formula (1).
  • the layer adjacent to the blue light emitting layer contains the arylamine compound represented by the general formula (1), the above 1) or The organic electroluminescence element according to 2).
  • R 4 to R 8 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.
  • R 5 and R 6 , and R 7 and R 8 may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • Y 1 to Y 3 are N-R 4 , CR 5 R 6 , or Si-R 7 R 8 , R 4 to R 8 are replaced or not replaced with adjacent Q 1 to Q 3, respectively.
  • Substituted or unsubstituted aromatic hydrocarbon group "substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted aromatic hydrocarbon group” represented by Ar 1 to Ar 4 in the general formula (1).
  • aromatic hydrocarbon group “aromatic heterocyclic group” or “condensed polycyclic aromatic group” in the “aromatic group” include a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group and an anthracenyl group.
  • the "substituent" in the "substituted aromatic hydrocarbon group", “substituted aromatic heterocyclic group” or “substituted condensed polycyclic aromatic group” represented by Ar 1 to Ar 4 in the general formula (1) Specifically, a heavy hydrogen atom, a cyano group, a nitro group; a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, an iodine atom; a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, Linear or branched alkyl groups with 1 to 6 carbon atoms such as isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, neopentyl group, n-hexyl group; methyloxy group, ethyloxy group, propyl A linear or
  • Arylalkyloxy groups such as groups; aromatic carbides such as phenyl group, biphenylyl group, terphenylyl group, naphthyl group, anthracenyl group, phenanthrenyl group, fluorenyl group, indenyl group, pyrenyl group, peryleneyl group, fluoranthenyl group, triphenylenyl group.
  • Hydrogen group or condensed polycyclic aromatic group pyridyl group, pyrimidinyl group, triazinyl group, thienyl group, furyl group, pyroryl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, indolyl group, carbazolyl group, benzoxazoli Aromatic heterocyclic groups such as ru group, benzothiazolyl group, quinoxalinyl group, benzoimidazolyl group, pyrazolyl group, dibenzofuranyl group, dibenzothienyl group, carbolinyl group; arylvinyl group such as styryl group and naphthylvinyl group; acetyl group, benzoyl An acyl group such as a group can be mentioned.
  • substituents may be further substituted with the above-exemplified substituents. Further, these substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • Formula (1) is represented by L 1 in the "divalent substituted or unsubstituted aromatic hydrocarbon", “divalent substituted or unsubstituted aromatic heterocyclic” or “substituted or unsubstituted As “divalent group of aromatic hydrocarbon”, “divalent group of aromatic heterocycle” or “divalent group of condensed polycyclic aromatic” in “divalent group of condensed polycyclic aromatic", specific
  • a phenylene group a biphenylene group, a terphenylene group, a tetrakisphenylene group, a naphthylene group, an anthylene group, a phenanthrylene group, a fluorenylene group, a phenanthrolylene group, an indenylene group, a pyrenylene group, a peryleneylene group, a fluoranthenylene group, a triphenylene group.
  • Ren group pyridinylene group, pyrimidinylene group, quinolylene group, isoquinolylene group, indolylene group, carbazolylen group, quinoxalylene group, benzoimidazolylene group, pyrazolylen group, naphthylidylene group, phenanthrolinylene group, acridinylene group, thiophenylene group, benzothio Examples thereof include a phenylene group, a benzothiazolylen group, and a dibenzothiophenylene group.
  • L 1 that there exist a plurality may be the same or different.
  • 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 3 in the general formula (1).
  • 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” has “1 to 1 to carbon atoms”.
  • Specific examples of the "linear or branched alkyl group of 6", “cycloalkyl group having 5 to 10 carbon atoms” or “linear or branched alkenyl group having 2 to 6 carbon atoms” be specific.
  • Linear or branched alkyl group having 1 to 6 carbon atoms having a substituent and "5 to 10 carbon atoms having a substituent” represented by R 1 to R 3 in the general formula (1).
  • substituents in the "cycloalkyl group” or “linear or branched alkenyl group having 2 to 6 carbon atoms having a substituent” include a heavy hydrogen atom, a cyano group, and a nitro group; Halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom; linear or branched alkyloxy group having 1 to 6 carbon atoms such as methyloxy group, ethyloxy group and propyloxy group; vinyl group and allyl Alkenyl groups such as groups; aryloxy groups such as phenyloxy groups and trilloxy groups; arylalkyloxy groups such as benzyloxy groups and phenethyloxy groups; pheny
  • Aromatic heterocyclic groups such as, etc. can be mentioned. These substituents may be further substituted with the above-exemplified substituents. Further, these substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • Linear or branched alkyloxy group having 1 to 6 carbon atoms having a substituent or “5 to 6 carbon atoms having a substituent” represented by R 1 to R 3 in the general formula (1).
  • the "substituent” in “10 cycloalkyloxy groups” is a linear or branched “linear or branched group having a substituent and having 1 to 6 carbon atoms” represented by R 1 to R 3 in the above general formula (1).
  • Alkyl group "Cycloalkyl group having 5 to 10 carbon atoms having a substituent” or "Linear or branched alkenyl group having 2 to 6 carbon atoms having a substituent” with respect to “substituent”
  • alkyl group "Cycloalkyl group having 5 to 10 carbon atoms having a substituent” or "Linear or branched alkenyl group having 2 to 6 carbon atoms having a substituent” with respect to “substituent”
  • the same ones as shown can be given, and the same ones can be given as possible modes.
  • Substituted or unsubstituted aromatic hydrocarbon group "substituted or unsubstituted aromatic heterocyclic group” or “substituted or unsubstituted aromatic hydrocarbon group” represented by R 1 to R 3 in the general formula (1).
  • the "aromatic hydrocarbon group”, “aromatic heterocyclic group” or “condensed polycyclic aromatic group” in the "ring aromatic group” is represented by Ar 1 to Ar 4 in the above general formula (1).
  • these groups may have a substituent, and as the substituent, "substituted aromatic hydrocarbon group” represented by Ar 1 to Ar 4 in the above general formula (1), "substituted aromatic complex".
  • substituted aromatic hydrocarbon group represented by Ar 1 to Ar 4 in the above general formula (1)
  • substituted aromatic complex The same as those shown for the "substituent” in the "ring group” or the “substituted condensed polycyclic aromatic group” can be mentioned, and the same can be mentioned as possible embodiments.
  • aryloxy group in the "substituted or unsubstituted aryloxy group” represented by R 1 to R 3 in the general formula (1) 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, a peryleneyloxy group and the like.
  • These groups may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring. Further, these groups may have a substituent, and as the substituent, "substituted aromatic hydrocarbon group” represented by Ar 1 to Ar 4 in the above general formula (1), "substituted aromatic complex". The same as those shown for the "substituent" in the "ring group” or the "substituted condensed polycyclic aromatic group” can be mentioned, and the same can be mentioned as possible embodiments.
  • substituted or unsubstituted aromatic hydrocarbon group or “substituted or unsubstituted condensed polycyclic aromatic group” is preferable, and substituted or unsubstituted.
  • a phenyl group, a naphthyl group, a phenanthrenyl group and a fluorenyl group are more preferable, and a substituted or unsubstituted phenyl group and a fluorenyl group having a substituent are particularly preferable.
  • a substituent of the phenyl group a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a phenanthrenyl group and a fluorenyl group are preferable, and as a substituent of the fluorenyl group, a methyl group and a phenyl group are preferable. Further, it is preferable that Ar 1 and Ar 2 are different from each other.
  • substituted or unsubstituted aromatic hydrocarbon group or "substituted or unsubstituted condensed polycyclic aromatic group” is preferable, and substituted or unsubstituted phenyl.
  • a group, a biphenylyl group, a naphthyl group, a phenanthrenyl group and a fluorenyl group are more preferable, and an unsubstituted phenyl group, an unsubstituted biphenylyl group, an unsubstituted naphthyl group and a fluorenyl group having a substituent are particularly preferable.
  • substituent of the fluorenyl group a methyl group and a phenyl group are preferable.
  • divalent substituted or unsubstituted aromatic hydrocarbon or “divalent fused substituted or unsubstituted polycyclic aromatic” is preferably, benzene, biphenyl , Naphthalene, or a divalent group formed by removing two hydrogen atoms from phenanthrene is more preferable, and a divalent group formed by removing two hydrogen atoms from benzene, that is, a phenylene group is particularly preferable.
  • an unsubstituted phenylene group is preferable, and the bonding mode of the phenylene group is a para-position-meta-position bond or a para-position-to-para-position bond, that is, a 1,3-phenylene group or a 1,4-phenylene. It is preferably a group.
  • N representing the number of L 1 represents an integer of 1 to 3, but is preferably 1 or 2.
  • R 1 and R 3 in the general formula (1) a hydrogen atom and a deuterium atom are preferable, and a hydrogen atom is more preferable from the viewpoint of synthesis.
  • R 2 in the general formula (1) a "substituted or unsubstituted aromatic hydrocarbon group" or a “substituted or unsubstituted condensed polycyclic aromatic group” is preferable, and a substituted or unsubstituted phenyl group or biphenylyl is preferable.
  • a group, a naphthyl group, a phenanthrenyl group and a fluorenyl group are more preferable, and an unsubstituted phenyl group, an unsubstituted biphenylyl group, an unsubstituted naphthyl group and a fluorenyl group having a substituent are particularly preferable.
  • the substituent of the fluorenyl group a methyl group and a phenyl group are preferable. It is preferable that Ar 3 , Ar 4 and R 2 are the same as each other.
  • Ar 1 in the above general formula (1) may be a substituted or unsubstituted phenyl group, and the substituent in the substituted phenyl may be a substituted or unsubstituted phenyl group or a naphthyl group.
  • Ar 2 in the above general formula (1) may be a substituted phenyl group, and the substituent in the substituted phenyl may be a substituted or unsubstituted phenyl group, a biphenylyl group, or a naphthyl group.
  • Ar 3 , Ar 4 and R 2 in the above general formula (1) may be an unsubstituted phenyl group, an unsubstituted biphenylyl group, an unsubstituted naphthyl group, a fluorenyl group having a substituent, or an unsubstituted phenyl group. good.
  • aromatic hydrocarbon in represented by Q 1 ⁇ Q 3 substituted or unsubstituted aromatic hydrocarbon "or” substituted or unsubstituted aromatic heterocyclic ring "in
  • aromatic heterocycles specifically, benzene, naphthalene, anthracene, fluorene, phenanthrene, pyridine, pyrimidine, triazine, pyrrole, furan, thiophene, quinoline, isoquinolin, inden, benzofuran, benzothiophene, indol, Examples thereof include indolin, carbazole, carbolin, benzoxazole, benzothiazole, quinoxalin, benzimidazole, pyrazole, dibenzofuran, dibenzothiophene, naphthylidine, phenanthroline and acrydin.
  • these may have a substituent, and as the substituent, a linear group having a substituent and having 1 to 6 carbon atoms represented by R 1 to R 3 in the general formula (1) or "Substituent” in “branched alkyl group", “cycloalkyl group having 5 to 10 carbon atoms having a substituent” or “linear or branched alkenyl group having 2 to 6 carbon atoms having a substituent” Can be given similar to those shown with respect to. Further, these substituents may be bonded to each other via a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom to form a ring.
  • B is defined as a boron atom
  • P is a phosphorus atom
  • the general formula (2) and Y 1 ⁇ Y 3 in the formula (3) may be the same or different from each other, N-R 4, C- R 5 R 6, O, S, Se or Si-R 7 R It is any one selected from 8.
  • N-R 4 is a nitrogen atom having R 4 as a substituent
  • CR 5 R 6 is a carbon atom having R 5 and R 6 as a substituent
  • O is an oxygen atom
  • S is a sulfur atom
  • Se is a selenium atom.
  • Si-R 7 R 8 is defined as a silicon atom having R 7 and R 8 as a substituent.
  • Y 1 to Y 3 in the general formulas (2) and (3) are N-R 4 , CR 5 R 6 , or Si-R 7 R 8 , they are represented by R 4 to R 8.
  • R 4 to R 8 A linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent, "a cycloalkyl group having 5 to 10 carbon atoms which may have a substituent" or ".
  • Linear or branched alkyl group having 1 to 6 carbon atoms and “Number of carbon atoms” in “linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent”
  • Specific examples of the "5 to 10 cycloalkyl group” or “linear or branched alkenyl group having 2 to 6 carbon atoms” include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and an n-.
  • these may have a substituent, and as the substituent, a linear group having a substituent and having 1 to 6 carbon atoms represented by R 1 to R 3 in the general formula (1) or "Substituent” in “branched alkyl group", “cycloalkyl group having 5 to 10 carbon atoms having a substituent” or “linear or branched alkenyl group having 2 to 6 carbon atoms having a substituent” Can be given similar to those shown with respect to.
  • Y 1 to Y 3 in the general formulas (2) and (3) are N-R 4 , CR 5 R 6 , or Si-R 7 R 8 , they are represented by R 4 to R 8.
  • Specific examples of the "linear or branched alkyloxy group having 1 to 6 carbon atoms" or "cycloalkyloxy group having 5 to 10 carbon atoms" in the above include methyloxy group, ethyloxy group and n-.
  • Propyloxy group isopropyloxy group, n-butyloxy group, tert-butyloxy group, n-pentyloxy group, n-hexyloxy group, cyclopentyloxy group, cyclohexyloxy group, cycloheptyloxy group, cyclooctyloxy group, 1- Examples thereof include an adamantyloxy group and a 2-adamantyloxy group.
  • these groups may have a substituent, and as the substituent, "a straight chain having a substituent and having 1 to 6 carbon atoms” represented by R 1 to R 3 in the general formula (1).
  • "Shaped or branched alkyl group” "Cycloalkyl group having 5 to 10 carbon atoms having a substituent” or "Linear or branched alkenyl group having 2 to 6 carbon atoms having a substituent” The same as those shown for "substituents" can be mentioned.
  • Y 1 to Y 3 in the general formulas (2) and (3) are N-R 4 , CR 5 R 6 , or Si-R 7 R 8 , they are represented by R 4 to R 8.
  • aromatic hydrocarbon group in the "substituted or unsubstituted aromatic hydrocarbon group” include a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, an anthrasenyl group, a phenanthrenyl group and the like. Further, these groups may have a substituent, and as the substituent, "a straight chain having a substituent and having 1 to 6 carbon atoms" represented by R 1 to R 3 in the general formula (1).
  • Y 1 to Y 3 in the general formulas (2) and (3) are N-R 4 , CR 5 R 6 , or Si-R 7 R 8 , they are represented by R 4 to R 8.
  • Specific examples of the "aryloxy group" in the "substituted or unsubstituted aryloxy group” include a phenyloxy group, a biphenylyloxy group, a terphenylyloxy group, a naphthyloxy group, an anthracenyloxy group, and a phenanthre. Examples thereof include a nyloxy group, a fluorenyloxy group, an indenyloxy group, a pyrenyloxy group, and a perylenyloxy group.
  • these groups may have a substituent, and as the substituent, "a straight chain having a substituent and having 1 to 6 carbon atoms” represented by R 1 to R 3 in the general formula (1).
  • "Shaped or branched alkyl group” "Cycloalkyl group having 5 to 10 carbon atoms having a substituent” or "Linear or branched alkenyl group having 2 to 6 carbon atoms having a substituent” The same as those shown for "substituents" can be mentioned.
  • the Y 1, N-R 4, O, S is preferably, O, S being more preferred.
  • X in the general formula (2) and the formula (3) may be B.
  • arylamine compounds represented by the general formula (1) which are preferably used for the organic EL device of the present embodiment, specific examples of preferable compounds are shown in FIGS. 1 to 12, but are limited to these compounds. It is not something that is done.
  • the arylamine compound represented by the general formula (1) may be purified by a column chromatograph, adsorption purification using silica gel, activated carbon, activated clay, etc., recrystallization or crystallization method using a solvent, sublimation purification method, or the like. .. Identification of the compound may be performed by NMR analysis. As physical property values, the melting point, the glass transition point (Tg), and the work function may be measured. 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 transportability and hole blocking property.
  • the compound used for the organic EL element of the present embodiment was purified by column chromatography, adsorption purification with silica gel, activated charcoal, activated white clay, etc., recrystallization and crystallization method with a solvent, sublimation purification method, and the like. After that, the one finally purified by the sublimation purification method may be used.
  • the melting point and glass transition point (Tg) are measured by a high-sensitivity differential scanning calorimeter (DSC3100SA, manufactured by Bruker XS) using powder.
  • the glass transition point of the compound represented by the general formula (1) is not particularly limited, but is preferably 80 ° C. or higher, and further preferably 100 ° C. or higher, from the viewpoint of stability of the formed thin film. It is preferably 110 ° C. or higher, and particularly preferably 110 ° C. or higher.
  • the upper limit of the glass transition point is not particularly limited, but for example, a compound having a temperature of 250 ° C. or lower can be adopted.
  • the work function is obtained by forming a 100 nm thin film on an ITO substrate and using an ionization potential measuring device (PYS-202, manufactured by Sumitomo Heavy Industries, Ltd.).
  • the work function of the thin-film vapor-deposited film having a film thickness of 100 nm prepared on the ITO substrate using the compound represented by the general formula (1) is not particularly limited, but is preferably larger than 5.4 eV.
  • the upper limit of the work function of this vapor-deposited film is not particularly limited, but for example, a thin-film film of 7.0 eV or less can be used.
  • the structure of the organic EL element of the present embodiment is composed of an anode, a hole transport layer, a light emitting layer, an electron transport layer and a cathode in order on the substrate, and holes between the anode and the hole transport layer.
  • Examples thereof include those having an injection layer, those having a hole blocking layer between the light emitting layer and the electron transport layer, and those having an electron injection layer between the electron transport layer and the anode.
  • the hole transport layer preferably has a two-layer structure of a first hole transport layer and a second hole transport layer, and the second hole transport layer in this case emits light. Adjacent to the layer, it functions as an electron blocking layer.
  • an electrode material having a large work function such as ITO or gold is used.
  • hole injection layer of the organic EL element of the present embodiment materials such as starburst type triphenylamine derivatives and various triphenylamine tetramers; porphyrin compounds typified by copper phthalocyanine; hexacyanoazatriphenylene and the like. Acceptant heterocyclic compounds, coating-type polymer materials, and the like can be used. These materials can be thin-film formed by a known method such as a spin coating method or an inkjet method in addition to the vapor deposition method.
  • the arylamine compound represented by the general formula (1) is used as the hole transport layer of the organic EL device of the present embodiment.
  • the hole-transporting material that can be mixed or used simultaneously with the arylamine compound represented by the general formula (1) include N, N'-diphenyl-N, N'-di (m-tolyl) benzidine (TPD).
  • TAPC 4- (di-4-tolylamino) phenyl] cyclohexane
  • compounds such as various triphenylamine derivatives can be used. These may be formed alone, or may be used as a single layer formed by mixing with other materials, and may be used as a single layer formed by themselves, layers formed by mixing, or layers formed by mixing. It may be a laminated structure of a layer formed by mixing with a layer formed alone. These materials can be thin-film formed by a known method such as a spin coating method or an inkjet method in addition to the vapor deposition method.
  • a material usually used for the layer is further P-doped with trisbromophenylamine hexachloroantimony, a radialene derivative (see, for example, Patent Document 7) or the like.
  • a polymer compound having the structure of a benzidine derivative such as TPD in its partial structure can be used.
  • the second hole transport layer adjacent to the light emitting layer is the general An arylamine compound represented by the formula (1).
  • Examples of the hole-transporting material that can be mixed or used simultaneously with the arylamine compound represented by the general formula (1) include 4,4', 4''-tri (N-carbazolyl) triphenylamine (TCTA).
  • 9,9-bis [4- (carbazole-9-yl) phenyl] fluorene 1,3-bis (carbazole-9-yl) benzene (mCP), 2,2-bis (4-carbazole-9-yl) Carbazole derivatives such as phenyl) adamantan (Ad-Cz), triphenyl represented by 9- [4- (carbazole-9-yl) phenyl] -9- [4- (triphenylsilyl) phenyl] -9H-fluorene Examples thereof include compounds having an electron blocking action, such as compounds having a silyl group and a triarylamine structure.
  • These may be formed alone, or may be used as a single layer formed by mixing with other materials, and may be used as a single layer formed by themselves, layers formed by mixing, or layers formed by mixing. It may be a laminated structure of a layer formed by mixing with a layer formed alone.
  • These materials can be thin-film formed by a known method such as a spin coating method or an inkjet method in addition to the vapor deposition method.
  • the light emitting layer of the organic EL element of the present embodiment in addition to metal complexes of quinolinol derivatives such as Alq 3 , various metal complexes, anthracene derivatives, bisstyrylbenzene derivatives, pyrene derivatives, oxazole derivatives, polyparaphenylene vinylene derivatives Etc. 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.
  • a heterocycle having an indole ring as a partial structure of the fused ring.
  • a compound, 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.
  • a pyrene derivative and a compound represented by the general formula (2) are preferably used, but in addition, quinacridone, coumarin, rubrene, perylene, and their derivatives, benzopyrene derivative, indenophenanthrene derivative, and rhodamine. Derivatives, aminostyryl derivatives and the like can be used.
  • These may be formed alone, or may be used as a single layer formed by mixing with other materials, and may be used as a single layer formed by themselves, layers formed by mixing, or layers formed by mixing. It may be a laminated structure of a layer formed by mixing with a layer formed alone.
  • a phosphorescent light emitter As the phosphorescent body, a phosphorescent body of a metal complex such as iridium or platinum can be used. 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) are used, and the host material at this time is positive.
  • carbazole derivatives such as 4,4'-di (N-carbazolyl) biphenyl (CBP), TCTA, and mCP can be used.
  • p-bis (triphenylsilyl) benzene (UGH2) and 2,2', 2''-(1,3,5-phenylene) -tris (1-phenyl-1H-benzimidazole) ) (TPBI) or the like can be used, and a high-performance organic EL element can be manufactured.
  • Doping of the phosphorescent luminescent material to the host material is preferably done by co-depositing in the range of 1 to 30% by weight with respect to the entire light emitting layer in order to avoid concentration quenching.
  • Non-Patent Document 3 a material that emits delayed fluorescence such as a CDCB derivative such as PIC-TRZ, CC2TA, PXZ-TRZ, 4CzIPN as a light emitting material.
  • a material that emits delayed fluorescence such as a CDCB derivative such as PIC-TRZ, CC2TA, PXZ-TRZ, 4CzIPN.
  • These materials can be thin-film formed by a known method such as a spin coating method or an inkjet method in addition to the vapor deposition method.
  • a phenanthroline derivative such as bathocuproine (BCP) or aluminum (III) bis (2-methyl-8-quinolinate) -4-phenylphenolate (hereinafter abbreviated as BAlq).
  • BCP bathocuproine
  • BAlq aluminum (III) bis (2-methyl-8-quinolinate) -4-phenylphenolate
  • compounds having a hole-blocking action such as various rare earth complexes, triazole derivatives, triazine derivatives, and oxaziazole derivatives can be used. These materials may also serve as materials for the electron transport layer.
  • These may be formed alone, or may be used as a single layer formed by mixing with other materials, and may be used as a single layer formed by themselves, layers formed by mixing, or layers formed by mixing. It may be a laminated structure of a layer formed by mixing with a layer formed alone.
  • These materials can be thin-film formed by a known method such as a spin coating method or an inkjet method in addition to the vapor deposition method.
  • metal complexes of quinolinol derivatives such as Alq 3 and BAlq, various metal complexes, triazole derivatives, triazine derivatives, oxadiazole derivatives, pyridine derivatives, pyrimidine derivatives, and benzimidazole.
  • quinolinol derivatives such as Alq 3 and BAlq
  • various metal complexes triazole derivatives, triazine derivatives, oxadiazole derivatives, pyridine derivatives, pyrimidine derivatives, and benzimidazole.
  • Derivatives, thianiazol derivatives, anthracene derivatives, carbodiimide derivatives, quinoxalin derivatives, pyridoindole derivatives, phenanthroline derivatives, silol derivatives and the like can be used.
  • These may be formed alone, or may be used as a single layer formed by mixing with other materials, and may be used as a single layer formed by themselves, layers formed by mixing, or layers formed by mixing. It may be a laminated structure of a layer formed by mixing with a layer formed alone.
  • These materials can be thin-film formed by a known method such as a spin coating method or an inkjet method in addition to the vapor deposition method.
  • alkali metal salts such as lithium fluoride and cesium fluoride
  • alkaline earth metal salts such as magnesium fluoride
  • metal complexes of quinolinol derivatives such as lithium quinolinol, aluminum oxide and the like.
  • Metal oxides of, or metals such as itterbium (Yb), samarium (Sm), calcium (Ca), strontium (Sr), cesium (Cs), etc. can be used, but in the preferred selection of electron transport layer and cathode. Can omit this.
  • a material usually used for the layer which is further N-doped with a metal such as cesium, can be used.
  • an electrode material having a low work function such as aluminum or an alloy having a lower work function such as a magnesium silver alloy, a magnesium indium alloy, or an aluminum magnesium alloy is used as an electrode material. ..
  • At least one layer of the layers arranged between the first hole transport layer and the electron transport layer contains the arylamine compound represented by the general formula (1).
  • it is preferable that at least one layer of the layers arranged between the first hole transport layer and the blue light emitting layer contains the arylamine compound represented by the general formula (1).
  • the layer adjacent to the blue light emitting layer among the layers arranged on the anode side of the blue light emitting layer contains the arylamine compound represented by the general formula (1).
  • the second hole transport layer contains the arylamine compound represented by the general formula (1).
  • 1.3 g of diphenylphosphinoferrocene palladium dichloride was added and heated, and the mixture was stirred at 100 ° C. for 16 hours. The mixture was cooled to 80 ° C., hot filtered and the filtrate was concentrated.
  • N, 4', 6'-triphenyl- [1,1': 2', 1 "-terphenyl] -4-amine 7.5 g, 1- (4-bromophenyl) in a nitrogen-substituted reaction vessel.
  • 7.4 g of -3-phenylnaphthalene, 75 mL of toluene, and 2.3 g of t-butoxysodium were added, and nitrogen gas was aerated while irradiating with ultrasonic waves for 30 minutes.
  • 0.1 g of palladium acetate and 0.3 g of a 50% (w / v) toluene solution of t-butylphosphine were added and heated, and the mixture was stirred at 100 ° C.
  • N- (4- (naphthalen-2-yl) phenyl) -4', 6'-diphenyl- [1,1': 2', 1''-terphenyl] -4-amine in a nitrogen-substituted reaction vessel 5.5 g, 2.6 g of 4-bromoterphenyl, 60 mL of toluene and 1.0 g of t-butoxysodium were added, and nitrogen gas was aerated while irradiating with ultrasonic waves for 30 minutes.
  • the glass transition point of the arylamine compound represented by the general formula (1) was measured by a high-sensitivity differential scanning calorimeter (DSC3100SA, manufactured by Bruker AXS). Glass transition point Compound of Example 1 128.8 ° C. Compound of Example 2 136.3 ° C. Compound of Example 3 127.3 ° C. Compound of Example 4 120.0 ° C. Compound of Example 5 115.0 ° C. Compound of Example 6 112.2 ° C. Compound of Example 7 117.7 ° C. Compound of Example 8 126.4 ° C. Compound of Example 9 124.1 ° C. Compound of Example 10 125.7 ° C. Compound of Example 11 128.9 ° C. Compound of Example 12 105.5 ° C.
  • the arylamine compound represented by the general formula (1) has a glass transition point of 100 ° C. or higher, indicating that the thin film state is stable.
  • a thin-film deposition film having a film thickness of 100 nm was prepared on an ITO substrate, and an ionization potential measuring device (PYS-202, manufactured by Sumitomo Heavy Industries, Ltd.) was used. The work function was measured.
  • the arylamine compound represented by the general formula (1) shows a suitable energy level as compared with the work function of 5.4 eV possessed by general hole transport materials such as NPD and TPD, and is good positive. It can be seen that it has hole transport capacity.
  • a glass substrate 1 having a reflective ITO electrode formed in advance as a transparent anode 2 is prepared, and a hole injection layer 3 and a first positive electrode are formed on the reflective ITO electrode.
  • the hole transport layer 4, the second hole transport 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 washed in isopropyl alcohol for 20 minutes. Drying was performed for 10 minutes on a hot plate heated to 250 ° C. Then, after performing UV ozone treatment for 15 minutes, the glass substrate with ITO was mounted in a vacuum vapor deposition machine and the pressure was reduced to 0.001 Pa or less.
  • a two-way vapor deposition was performed on the transparent anode 2 to form a hole injection layer 3 covering the transparent anode 2 so as to have a film thickness of 10 nm.
  • a first hole transport layer 4 was formed on the hole injection layer 3 with a compound (HTM-1) having the following structural formula so as to have a film thickness of 140 nm.
  • the second hole transport layer 5 was formed with the compound (1-80) of Example 1 so as to have a film thickness of 5 nm.
  • the electron transport layer 7 was formed to have a film thickness of 30 nm by two-way vapor deposition at a vapor deposition rate of 50.
  • An electron injection layer 8 was formed on the electron transport layer 7 with lithium fluoride so as to have a film thickness of 1 nm.
  • a cathode 9 was formed on the electron injection layer 8 with a magnesium-silver alloy so as to have a film thickness of 12 nm.
  • the capping layer 10 was formed to have a film thickness of 60 nm by using a compound (CPL-1) having the following structural formula.
  • the physical properties of the produced organic EL device were measured in the air at room temperature. Table 1 summarizes the measurement results of the light emission characteristics when a DC voltage is applied to the produced organic EL device.
  • Example 16 the organic EL under the same conditions except that the compound (1-120) of Example 2 was used instead of the compound (1-80) of Example 1 as the material of the second hole transport layer 5. The element was manufactured. The characteristics of the produced organic EL device were measured in the air at room temperature. Table 1 summarizes the measurement results of the light emission characteristics when a DC voltage is applied to the produced organic EL element.
  • Example 16 the organic EL under the same conditions except that the compound (1-81) of Example 3 was used instead of the compound (1-80) of Example 1 as the material of the second hole transport layer 5.
  • the element was manufactured.
  • the characteristics of the produced organic EL device were measured in the air at room temperature. Table 1 summarizes the measurement results of the light emission characteristics when a DC voltage is applied to the produced organic EL element.
  • Example 16 the organic EL under the same conditions except that the compound (1-79) of Example 4 was used instead of the compound (1-80) of Example 1 as the material of the second hole transport layer 5.
  • the element was manufactured.
  • the characteristics of the produced organic EL device were measured in the air at room temperature. Table 1 summarizes the measurement results of the light emission characteristics when a DC voltage is applied to the produced organic EL element.
  • Example 16 the organic EL under the same conditions except that the compound (1-18) of Example 5 was used instead of the compound (1-80) of Example 1 as the material of the second hole transport layer 5.
  • the element was manufactured.
  • the characteristics of the produced organic EL device were measured in the air at room temperature. Table 1 summarizes the measurement results of the light emission characteristics when a DC voltage is applied to the produced organic EL element.
  • Example 16 the organic EL under the same conditions except that the compound (1-138) of Example 6 was used instead of the compound (1-80) of Example 1 as the material of the second hole transport layer 5. The element was manufactured. The characteristics of the produced organic EL device were measured in the air at room temperature. Table 1 summarizes the measurement results of the light emission characteristics when a DC voltage is applied to the produced organic EL element.
  • Example 16 the organic EL under the same conditions except that the compound (1-151) of Example 7 was used instead of the compound (1-80) of Example 1 as the material of the second hole transport layer 5. The element was manufactured. The characteristics of the produced organic EL device were measured in the air at room temperature. Table 1 summarizes the measurement results of the light emission characteristics when a DC voltage is applied to the produced organic EL element.
  • Example 16 the organic EL under the same conditions except that the compound (1-156) of Example 8 was used instead of the compound (1-80) of Example 1 as the material of the second hole transport layer 5.
  • the element was manufactured.
  • the characteristics of the produced organic EL device were measured in the air at room temperature. Table 1 summarizes the measurement results of the light emission characteristics when a DC voltage is applied to the produced organic EL element.
  • Example 16 the organic EL under the same conditions except that the compound (1-159) of Example 9 was used instead of the compound (1-80) of Example 1 as the material of the second hole transport layer 5.
  • the element was manufactured.
  • the characteristics of the produced organic EL device were measured in the air at room temperature. Table 1 summarizes the measurement results of the light emission characteristics when a DC voltage is applied to the produced organic EL element.
  • Example 16 the organic EL under the same conditions except that the compound (1-162) of Example 10 was used instead of the compound (1-80) of Example 1 as the material of the second hole transport layer 5.
  • the element was manufactured.
  • the characteristics of the produced organic EL device were measured in the air at room temperature. Table 1 summarizes the measurement results of the light emission characteristics when a DC voltage is applied to the produced organic EL element.
  • Example 16 the organic EL under the same conditions except that the compound (1-167) of Example 11 was used instead of the compound (1-80) of Example 1 as the material of the second hole transport layer 5. The element was manufactured. The characteristics of the produced organic EL device were measured in the air at room temperature. Table 1 summarizes the measurement results of the light emission characteristics when a DC voltage is applied to the produced organic EL element.
  • Example 16 the organic EL under the same conditions except that the compound (1-171) of Example 12 was used instead of the compound (1-80) of Example 1 as the material of the second hole transport layer 5. The element was manufactured. The characteristics of the produced organic EL device were measured in the air at room temperature. Table 1 summarizes the measurement results of the light emission characteristics when a DC voltage is applied to the produced organic EL element.
  • Example 16 For comparison, the same applies to Example 16 except that the compound (HTM-2) having the following structural formula was used in place of the compound (1-80) of Example 1 as the material of the second hole transport layer 5.
  • An organic EL device was manufactured under the conditions of. The characteristics of the produced organic EL device were measured in the air at room temperature. Table 1 summarizes the measurement results of the light emission characteristics when a DC voltage is applied to the produced organic EL element.
  • Example 2 For comparison, the same applies to Example 16 except that the compound (HTM-3) having the following structural formula was used in place of the compound (1-80) of Example 1 as the material of the second hole transport layer 5.
  • An organic EL device was manufactured under the conditions of. The characteristics of the produced organic EL device were measured in the air at room temperature. Table 1 summarizes the measurement results of the light emission characteristics when a DC voltage is applied to the produced organic EL element.
  • Table 1 summarizes the results of measuring the device life using the organic EL devices produced in Examples 16 to 27 and Comparative Examples 1 and 2.
  • the element life is equivalent to 95% when the emission brightness (initial brightness) at the start of light emission is 2000 cd / m 2 and the constant current drive is performed, and the emission brightness is 1900 cd / m 2 (when the initial brightness is 100%). It was measured as the time until it decayed to 95% decay).
  • the luminous efficiency when a current with a current density of 10 mA / cm 2 was passed was 8.97 to 9.15 cd / A of the organic EL elements of Comparative Examples 1 and 2, and the light emission efficiencies of Examples 16 to 9.
  • the 27 organic EL devices had high efficiency of 9.45 to 10.46 cd / A.
  • the power efficiency of the organic EL elements of Comparative Examples 1 and 2 is as high as 8.19 to 8.23 lm / W, whereas that of the organic EL elements of Examples 16 to 27 is as high as 8.63 to 9.53 lm / W. It was efficient.
  • the element life (95% attenuation) is extended to 307 to 662 hours for the organic EL elements of Examples 16 to 27, as opposed to 245 to 269 hours for the organic EL elements of Comparative Examples 1 and 2. I understand.
  • the arylamine compound having a specific structure represented by the general formula (1) has a higher hole mobility than the conventional arylamine compounds of Comparative Examples 1 and 2. It has excellent electron blocking ability. Therefore, it has been found that the organic EL element used together with the light emitting layer of the present disclosure can realize an organic EL element having high luminous efficiency and a long life as compared with the conventional organic EL element.
  • the organic EL device using the arylamine compound having a specific structure of the present invention can improve the luminous efficiency and the durability of the organic EL device, for example, for home electric appliances and lighting applications. Can be deployed.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
PCT/JP2021/002068 2020-01-22 2021-01-21 有機エレクトロルミネッセンス素子 Ceased WO2021149773A1 (ja)

Priority Applications (5)

Application Number Priority Date Filing Date Title
KR1020227024229A KR102876616B1 (ko) 2020-01-22 2021-01-21 유기 일렉트로 루미네선스 소자
CN202180010435.2A CN114981991A (zh) 2020-01-22 2021-01-21 有机电致发光元件
JP2021572796A JP7498727B2 (ja) 2020-01-22 2021-01-21 有機エレクトロルミネッセンス素子
EP21744719.2A EP4095216A4 (en) 2020-01-22 2021-01-21 ORGANIC ELECTROLUMINESCENT ELEMENT
US17/792,001 US20230101400A1 (en) 2020-01-22 2021-01-21 Organic electroluminescent element

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2020-008577 2020-01-22
JP2020008577 2020-01-22

Publications (1)

Publication Number Publication Date
WO2021149773A1 true WO2021149773A1 (ja) 2021-07-29

Family

ID=76992506

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2021/002068 Ceased WO2021149773A1 (ja) 2020-01-22 2021-01-21 有機エレクトロルミネッセンス素子

Country Status (7)

Country Link
US (1) US20230101400A1 (https=)
EP (1) EP4095216A4 (https=)
JP (1) JP7498727B2 (https=)
KR (1) KR102876616B1 (https=)
CN (1) CN114981991A (https=)
TW (1) TWI888475B (https=)
WO (1) WO2021149773A1 (https=)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023013575A1 (ja) * 2021-08-03 2023-02-09 保土谷化学工業株式会社 有機エレクトロルミネッセンス素子
TWI920358B (zh) 2021-08-03 2026-04-01 日商保土谷化學工業股份有限公司 有機電致發光元件

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3605638B1 (en) * 2017-03-28 2023-11-08 Hodogaya Chemical Co., Ltd. Organic electroluminescent device

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0848656A (ja) 1994-02-08 1996-02-20 Tdk Corp 有機ｅｌ素子用化合物および有機ｅｌ素子
JP3194657B2 (ja) 1993-11-01 2001-07-30 松下電器産業株式会社 電界発光素子
JP2006151979A (ja) 2004-11-29 2006-06-15 Samsung Sdi Co Ltd フェニルカルバゾール系化合物とその製造方法及び有機電界発光素子
WO2008062636A1 (fr) 2006-11-24 2008-05-29 Idemitsu Kosan Co., Ltd. Dérivé d'amine aromatique et élément électroluminescent organique utilisant celui-ci
JP4943840B2 (ja) 2004-05-25 2012-05-30 保土谷化学工業株式会社 ｐ−ターフェニル化合物および該化合物を用いた電子写真用感光体
JP5040216B2 (ja) 2005-08-30 2012-10-03 三菱化学株式会社 有機化合物、電荷輸送材料、有機電界発光素子用材料、電荷輸送材料組成物及び有機電界発光素子
WO2014009310A1 (en) 2012-07-09 2014-01-16 Novaled Ag Doped organic semiconductive matrix material
WO2016199743A1 (ja) * 2015-06-11 2016-12-15 保土谷化学工業株式会社 アリールアミン化合物および有機エレクトロルミネッセンス素子
WO2019164331A1 (ko) * 2018-02-23 2019-08-29 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
JP2020008577A (ja) 2018-07-05 2020-01-16 ビーボップ センサーズ、インコーポレイテッド フリーサイズのデータグローブ
JP2020083896A (ja) * 2018-11-30 2020-06-04 エスエフシー カンパニー リミテッド 多環芳香族誘導体化合物及びこれを用いた有機発光素子

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105378964B (zh) * 2013-07-12 2018-01-09 保土谷化学工业株式会社 有机电致发光器件
US10593884B2 (en) * 2015-01-06 2020-03-17 Hodogaya Chemical Co., Ltd. Organic electroluminescent device
US11594683B2 (en) * 2015-10-29 2023-02-28 Hodogaya Chemical Co., Ltd. Organic electroluminescent device
WO2017122813A1 (ja) * 2016-01-14 2017-07-20 保土谷化学工業株式会社 有機エレクトロルミネッセンス素子
EP3544073A4 (en) * 2016-11-16 2020-11-25 Hodogaya Chemical Co., Ltd. ORGANIC ELECTROLUMINESCENT ELEMENT
JP7163311B2 (ja) * 2017-12-05 2022-10-31 保土谷化学工業株式会社 有機エレクトロルミネッセンス素子
CN113853377B (zh) * 2019-11-29 2024-05-14 株式会社Lg化学 杂环化合物和包含其的有机发光器件

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3194657B2 (ja) 1993-11-01 2001-07-30 松下電器産業株式会社 電界発光素子
JPH0848656A (ja) 1994-02-08 1996-02-20 Tdk Corp 有機ｅｌ素子用化合物および有機ｅｌ素子
JP4943840B2 (ja) 2004-05-25 2012-05-30 保土谷化学工業株式会社 ｐ−ターフェニル化合物および該化合物を用いた電子写真用感光体
JP2006151979A (ja) 2004-11-29 2006-06-15 Samsung Sdi Co Ltd フェニルカルバゾール系化合物とその製造方法及び有機電界発光素子
JP5040216B2 (ja) 2005-08-30 2012-10-03 三菱化学株式会社 有機化合物、電荷輸送材料、有機電界発光素子用材料、電荷輸送材料組成物及び有機電界発光素子
WO2008062636A1 (fr) 2006-11-24 2008-05-29 Idemitsu Kosan Co., Ltd. Dérivé d'amine aromatique et élément électroluminescent organique utilisant celui-ci
WO2014009310A1 (en) 2012-07-09 2014-01-16 Novaled Ag Doped organic semiconductive matrix material
WO2016199743A1 (ja) * 2015-06-11 2016-12-15 保土谷化学工業株式会社 アリールアミン化合物および有機エレクトロルミネッセンス素子
WO2019164331A1 (ko) * 2018-02-23 2019-08-29 주식회사 엘지화학 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자
JP2020008577A (ja) 2018-07-05 2020-01-16 ビーボップ センサーズ、インコーポレイテッド フリーサイズのデータグローブ
JP2020083896A (ja) * 2018-11-30 2020-06-04 エスエフシー カンパニー リミテッド 多環芳香族誘導体化合物及びこれを用いた有機発光素子

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
APPL. PHYS. LET., vol. 98, 2011, pages 083302
JAPAN SOCIETY OF APPLIED PHYSICS NINTH WORKSHOP PREPRINT, 2001, pages 23 - 31
ORGANIC EL DEBATE THIRD REGULAR MEETING PREPRINT, 2006, pages 13 - 14
See also references of EP4095216A4

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023013575A1 (ja) * 2021-08-03 2023-02-09 保土谷化学工業株式会社 有機エレクトロルミネッセンス素子
TWI920358B (zh) 2021-08-03 2026-04-01 日商保土谷化學工業股份有限公司 有機電致發光元件

Also Published As

Publication number Publication date
KR20220131235A (ko) 2022-09-27
JP7498727B2 (ja) 2024-06-12
US20230101400A1 (en) 2023-03-30
TW202136472A (zh) 2021-10-01
KR102876616B1 (ko) 2025-10-24
JPWO2021149773A1 (https=) 2021-07-29
TWI888475B (zh) 2025-07-01
CN114981991A (zh) 2022-08-30
EP4095216A1 (en) 2022-11-30
EP4095216A4 (en) 2024-04-03

Similar Documents

Publication Publication Date Title
JP6815326B2 (ja) 有機エレクトロルミネッセンス素子
TWI631095B (zh) 有機電致發光元件
US20170179398A1 (en) Organic electroluminescent device
KR102813012B1 (ko) 트리아릴아민 구조를 갖는 화합물 및 유기 일렉트로 루미네선스 소자
JPWO2011155169A1 (ja) アクリダン環構造を有する化合物および有機エレクトロルミネッセンス素子
JP7018895B2 (ja) 有機エレクトロルミネッセンス素子
JP6901977B2 (ja) 有機エレクトロルミネッセンス素子
JP6810710B2 (ja) 有機エレクトロルミネッセンス素子
JP6807849B2 (ja) 有機エレクトロルミネッセンス素子
JP7149263B2 (ja) 有機エレクトロルミネッセンス素子
KR102785437B1 (ko) 유기 일렉트로루미네선스 소자
WO2021256515A1 (ja) 有機エレクトロルミネッセンス素子
WO2021177022A1 (ja) 有機エレクトロルミネッセンス素子
JP7498727B2 (ja) 有機エレクトロルミネッセンス素子
JPWO2020111077A1 (ja) 有機エレクトロルミネッセンス素子
KR102829841B1 (ko) 유기 일렉트로루미네센스 소자
JP7065029B2 (ja) アリールジアミン化合物及び有機エレクトロルミネッセンス素子
JP7827627B2 (ja) 有機エレクトロルミネッセンス素子
JP7771065B2 (ja) 有機エレクトロルミネッセンス素子
JP2020136517A (ja) 有機エレクトロルミネッセンス素子
KR102316844B1 (ko) 유기 일렉트로 루미네센스 소자
KR20240114741A (ko) 아릴아민 화합물, 유기 일렉트로루미네센스 소자 및 전자 기기
WO2022097574A1 (ja) 有機エレクトロルミネッセンス素子
KR20250047744A (ko) 아릴아민 화합물, 유기 일렉트로루미네센스 소자 및 전자 기기
WO2021149735A1 (ja) アリールアミン化合物および有機エレクトロルミネッセンス素子

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 21744719

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2021572796

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

ENP Entry into the national phase

Ref document number: 2021744719

Country of ref document: EP

Effective date: 20220822