WO2024237322A1 - 芳香族化合物、有機エレクトロルミネッセンス素子および電子機器 - Google Patents

芳香族化合物、有機エレクトロルミネッセンス素子および電子機器 Download PDF

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WO2024237322A1
WO2024237322A1 PCT/JP2024/018212 JP2024018212W WO2024237322A1 WO 2024237322 A1 WO2024237322 A1 WO 2024237322A1 JP 2024018212 W JP2024018212 W JP 2024018212W WO 2024237322 A1 WO2024237322 A1 WO 2024237322A1
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大貴 平井
ヒョン旭 車
煕載 金
幸喜 加瀬
雄太 平山
秀一 林
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Hodogaya Chemical Co Ltd
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Priority to CN202480033343.XA priority patent/CN121219258A/zh
Priority to EP24807272.0A priority patent/EP4714935A1/en
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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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    • C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C233/62—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
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    • C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C69/753—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of polycyclic acids
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    • 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
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/85—Arrangements for extracting light from the devices
    • H10K50/858—Arrangements for extracting light from the devices comprising refractive means, e.g. lenses
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/10—OLED displays
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    • 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]
    • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
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    • 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
    • H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/58—Ring systems containing bridged rings containing three rings
    • C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
    • C07C2603/74—Adamantanes

Definitions

  • the present invention relates to an aromatic compound suitable as a material for organic electroluminescence elements (hereinafter referred to as organic EL elements), which are self-luminous elements suitable for various display devices, and electronic devices.
  • organic EL elements organic electroluminescence elements
  • the present invention relates to an aromatic compound with excellent low refractive index characteristics, and also to an organic EL element and electronic device that use the aromatic compound.
  • C. W. Tang et al. of Eastman Kodak Company made organic EL elements using organic materials practical by developing a layered structure element in which various roles are assigned to each material. They layered a phosphor capable of transporting electrons and an organic material capable of transporting holes, and injected both charges into the phosphor layer to emit light, thereby obtaining a high brightness of 1000 cd/ m2 or more at a voltage of 10 V or less (see Patent Documents 1 and 2).
  • a semi-transparent electrode such as LiF/Al/Ag (see, for example, Non-Patent Document 1), Ca/Mg (see Non-Patent Document 2), or LiF/MgAg is used for the cathode.
  • an organic optical device has also been proposed in which a low refractive index layer formed by co-evaporating an additive for adjusting the refractive index and an organic semiconductor material is laminated with a high refractive index layer, and the optical interference effect of the laminated film is utilized to effectively control light propagation (see Patent Document 3).
  • the low refractive index layer in this case is formed by co-evaporation of the organic semiconductor material and additives, and controlling the amount of additive added and the film formation conditions is complicated. For this reason, there is a demand for the development of a material that exhibits excellent low refractive index characteristics even when evaporated alone.
  • the inventors have conducted extensive research with the aim of providing a material with excellent low refractive index characteristics. Furthermore, they have conducted extensive research with the aim of providing an organic EL element with high luminous efficiency.
  • an aromatic compound having a structure in which two phenylene groups having a substituent containing an amide structure or a substituent containing an ester structure are bonded to an alkanediyl, cycloalkanediyl, or fluorenediyl exhibits excellent low refractive index characteristics. They have also found that by providing a capping layer in which a low refractive index layer containing this aromatic compound is laminated with a high refractive index layer, an organic EL element with improved light extraction efficiency can be realized.
  • the present invention has been proposed based on these findings, and specifically has the following configuration.
  • a 1 in the general formula (a) and A 2 in the general formula (b) are each independently a divalent group represented by the following formula (c), formula (d), formula (e), formula (f), or formula (g).
  • Ak1 and Ak2 each independently represent a hydrogen atom, an unsubstituted alkyl group, or an unsubstituted haloalkyl group, and the dashed line represents a bonding site.
  • L 1 and L 2 in the general formula (a) and L 3 and L 4 in the general formula (b) each independently represent a single bond, -O-, -NH-, a substituted or unsubstituted methylene group, a substituted or unsubstituted ethanediyl group, or a substituted or unsubstituted propanediyl group.
  • Cy 1 and Cy 2 in the general formula (a) and Cy 3 and Cy 4 in the general formula (b) each independently represent a substituted or unsubstituted methyl group, a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted norbornyl group, a substituted or unsubstituted adamantyl group, or a substituted or unsubstituted phenyl group.
  • An organic EL element having at least an anode electrode, a hole transport layer, a light-emitting layer, an electron transport layer, a cathode electrode, and a capping layer in this order, the capping layer containing an aromatic compound according to any one of 1) to 5).
  • the organic EL element described in 6 in which the aromatic compound, when vacuum-deposited on a silicon substrate to a thickness of 80 nm, exhibits a refractive index of 1.70 or less at room temperature (25 ⁇ 2°C) for light having a wavelength of 400 nm or more and 700 nm or less.
  • An electronic element or electronic device having a pair of electrodes and at least one organic layer, the organic layer containing an aromatic compound described in any one of 1) to 5).
  • the aromatic compound of the present invention has excellent low refractive index characteristics, and therefore, by combining a low refractive index layer formed using the compound with a high refractive index layer, an organic EL element having improved luminous efficiency due to the optical interference effect can be realized.
  • the aromatic compound of the present invention can be used not only in organic EL devices but also in the field of electronic devices such as electrophotographic photoreceptors, image sensors, photoelectric conversion elements, and solar cells.
  • FIG. 1 is a diagram showing an example of the configuration of an organic EL element of the present invention.
  • the term "substituted or unsubstituted” means that the group to which the term is attached may be an unsubstituted group (a group in which hydrogen atoms are not substituted with a substituent), or at least one hydrogen atom of the group may be substituted with a substituent.
  • “transparent” means that the transmittance of visible light is 50% or more, for example, 80% or more, for example, 90% or more, for example, 99% or more. The transmittance of visible light can be measured by an ultraviolet-visible spectrophotometer.
  • the compound of the present invention is an aromatic compound represented by the following general formula (a) or (b).
  • R 1 to R 8 in general formula (a) and R 9 to R 16 in general formula (b) each independently represent a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted monovalent aromatic hydrocarbon group, or a substituted or unsubstituted monovalent aromatic heterocyclic group.
  • R 1 to R 16 may be the same or different from each other.
  • Cy 1 and Cy 2 in general formula (a) and Cy 3 and Cy 4 in general formula (b) each independently represent a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, or a substituted or unsubstituted monovalent aromatic hydrocarbon group. Cy 1 to Cy 4 may be the same or different from each other.
  • the "halogen atom" represented by R 1 to R 8 in general formula (a) and R 9 to R 16 in general formula (b) includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, of which a fluorine atom and a chlorine atom are preferred, and a fluorine atom is particularly preferred.
  • alkyl group in the "substituted or unsubstituted alkyl group” represented by R 1 to R 8 , Cy 1 and Cy 2 in general formula (a) and R 9 to R 16 , Cy 3 and Cy 4 in general formula (b) may be linear or branched.
  • the number of carbon atoms in the alkyl group is, for example, 1 to 40, and may be 1 to 30, 1 to 20, 1 to 10 or 1 to 6.
  • alkyl group examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, and a t-butyl group, among which a methyl group, an isopropyl group, and a t-butyl group are preferred, and a t-butyl group is particularly preferred.
  • the "cycloalkyl group" in the "substituted or unsubstituted cycloalkyl group” represented by R 1 to R 8 , Cy 1 and Cy 2 in the general formula (a) and R 9 to R 16 , Cy 3 and Cy 4 in the general formula (b) may be a monocyclic cycloalkyl group or a polycyclic cycloalkyl group.
  • Examples of the polycyclic cycloalkyl group include a bicycloalkyl group and a tricycloalkyl group.
  • the number of carbon atoms in the cycloalkyl group is, for example, 3 to 40, and may be 5 to 30, 5 to 20, or 5 to 10.
  • cycloalkyl group examples include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a norbornyl group, and an adamantyl group, and the like.
  • the cyclohexyl group, the cyclooctyl group, the norbornyl group, and the adamantyl group are preferred, and the norbornyl group and the adamantyl group are particularly preferred.
  • the "monovalent aromatic hydrocarbon group” may be a monocyclic aromatic hydrocarbon group, or may be composed of a fused ring in which two or more rings are fused, or a linked ring in which two or more rings are linked by a single bond.
  • each of the rings constituting the fused ring constituting the monovalent aromatic hydrocarbon group may be an aromatic hydrocarbon ring (e.g., a benzene ring) or an aliphatic hydrocarbon ring, but the fused rings as a whole are an aromatic hydrocarbon ring.
  • the number of carbon atoms of the monovalent aromatic hydrocarbon group is, for example, 6 to 40, may be 6 to 30, 6 to 20, or may be 6 to 14.
  • the "monovalent aromatic hydrocarbon group” include a phenyl group, a biphenylyl group, a 1-naphthyl group, a 2-naphthyl group, a 2-phenanthrenyl group, a 9-phenanthrenyl group, and a fluorenyl group, of which a phenyl group, a biphenylyl group, a 1-naphthyl group, a 2-naphthyl group, and a fluorenyl group are preferred, and a phenyl group is particularly preferred.
  • the "monovalent aromatic heterocyclic group” may be a monocyclic aromatic heterocyclic group, or may be composed of a condensed ring in which two or more rings are condensed.
  • the multiple constituent rings of the condensed ring constituting the monovalent aromatic heterocyclic group may all be heterocyclic, or may contain a heterocyclic ring and a hydrocarbon ring (e.g., a benzene ring).
  • the heterocyclic ring and the hydrocarbon ring as the constituent ring may be an aromatic ring or an aliphatic ring, but the condensed ring as a whole is an aromatic heterocyclic ring.
  • the heteroatom contained in the heteroaryl group include a nitrogen atom, a sulfur atom, and an oxygen atom.
  • the heteroatom contained in the monovalent aromatic heterocyclic group may be one or two or more. When the monovalent aromatic heterocyclic group contains two or more heteroatoms, the heteroatoms may be the same or different.
  • the number of atoms constituting the ring skeleton of the monovalent aromatic heterocyclic group is, for example, 4 to 40, and may be 5 to 20, 5 to 16, or 6 to 14.
  • the number of carbon atoms of the heteroaryl group is, for example, 3 to 35, and may be 3 to 30, or 2 to 20.
  • Specific examples of the "monovalent aromatic heterocyclic group" include a pyridyl group, a thienyl group, a furyl group, a pyrrolyl group, a quinolyl group, an isoquinolyl group, a benzofuranyl group, a benzothienyl group, an indolyl group, a carbazolyl group, a benzoxazolyl group, a benzothiazolyl group, a quinoxalinyl group, a benzimidazolyl group, a pyrazolyl group, a dibenzofuranyl group, a dibenzothienyl group, and a carbolinyl group, among which a pyridyl group, a benzofuranyl group, a dibenzofuranyl group, a benzothienyl
  • the alkyl groups, cycloalkyl groups and monovalent aromatic hydrocarbon groups in R 1 to R 8 , Cy 1 and Cy 2 in general formula (a) and R 9 to R 16 , Cy 3 and Cy 4 in general formula (b) may be unsubstituted or at least one hydrogen atom may be substituted with a substituent.
  • the monovalent aromatic heterocyclic groups in R 1 to R 8 in general formula (a) and R 9 to R 16 in general formula (b) may be unsubstituted or at least one hydrogen atom may be substituted with a substituent.
  • substituted alkyl group examples include a cyano group, a nitro group; a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom; a silyl group such as a trimethylsilyl group or a triphenylsilyl group; a linear or branched alkyl group having 1 to 6 carbon atoms such as a methyl group, an ethyl group, or a propyl group; a linear or branched haloalkyl group having 1 to 6 carbon atoms such as a trifluoromethyl group, a pentafluoroethyl group, a perfluoro-n-propyl group, a perfluorois
  • substituents of a benzene ring including a benzene ring that is a constituent ring of a condensed ring
  • the benzene rings substituted with the substituents, or the multiple substituents substituted on the same benzene ring 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.
  • substituents of the methylene group see the description of the "substituent" in the above "substituted alkyl group” etc.
  • a 1 in the general formula (a) and A 2 in the general formula (b) each independently represent a substituted or unsubstituted alkanediyl group, a substituted or unsubstituted cycloalkanediyl group, or a substituted or unsubstituted fluorenediyl group.
  • a 1 and A 2 may be the same or different from each other.
  • L 1 and L 2 in the general formula (a) and L 3 and L 4 in the general formula (b) each independently represent a single bond, -O-, -NH-, or a substituted or unsubstituted alkanediyl group.
  • L 1 to L 4 may be the same or different from each other.
  • X 1 and X 2 in the general formula (a) and X 3 and X 4 in the general formula (b) each independently represent -O- or -NH-.
  • X 1 to X 4 may be the same or different from each other.
  • the "alkanediyl group” represented by A 1 , L 1 and L 2 in general formula (a) and A 2 , L 3 and L 4 in general formula (b)
  • the "alkanediyl group” is a divalent group obtained by removing one hydrogen atom from an alkyl group.
  • alkyl group with “alkanediyl group”.
  • alkanediyl group include divalent groups obtained by removing one hydrogen atom from the specific examples of the "alkyl group” in R 1 to R 8 etc. above.
  • the "cycloalkanediyl group” is a divalent group obtained by removing one hydrogen atom from a "cycloalkyl group”.
  • cycloalkyl group examples include divalent groups obtained by removing one hydrogen atom from the specific examples of the “cycloalkanediyl group” in R 1 to R 8 etc. above.
  • the alkanediyl group in A 1 , L 1 and L 2 in general formula (a) and A 2 , L 3 and L 4 in general formula (b) may be unsubstituted, or at least one hydrogen atom of the alkanediyl group may be substituted with a substituent.
  • the cycloalkanediyl group and fluorenediyl group in A 1 in general formula (a) and A 2 in general formula (b) may be unsubstituted, or at least one hydrogen atom of the cycloalkanediyl group and fluorenediyl group may be substituted with a substituent.
  • alkanediyl group in A1 of general formula (a) and A2 of general formula (b) is a group represented by the following formula (c).
  • Ak 1 and Ak 2 each independently represent a hydrogen atom, an unsubstituted alkyl group, or an unsubstituted haloalkyl group, and the dashed line represents a bonding site (a single bond that bonds the carbon atom at the base end of the dashed line to the carbon atom of the benzene ring).
  • Ak 1 and Ak 2 may be the same or different from each other.
  • the description of the "alkyl group" in the above R1 to R8 etc. can be referred to.
  • alkyl group examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group etc., with a methyl group, an isopropyl group and a t-butyl group being preferred, and a methyl group being particularly preferred.
  • the "haloalkyl group” is an alkyl group in which at least one hydrogen atom has been substituted with a halogen atom.
  • the description of the "alkyl group” and the “halogen atom” in R 1 to R 8 and the like above can be referred to.
  • haloalkyl group examples include a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a perfluoro-n-propyl group, a perfluoroisopropyl group, a perfluoro-n-butyl group, a perfluoro-t-butyl group, and the like, with a trifluoromethyl group, a perfluoroisopropyl group, and a perfluoro-t-butyl group being preferred, and a trifluoromethyl group being particularly preferred.
  • Examples of the "cycloalkanediyl group" in A1 of general formula (a) and A2 of general formula (b) include groups represented by any of the following formulae (d) to (f).
  • the dashed lines represent the bonding sites (single bonds connecting the carbon atom at the base end of the dashed line to the carbon atom of the benzene ring).
  • Cy 1 -L 1 -X 1 -C( ⁇ O)- and Cy 2 -L 2 -X 2 -C( ⁇ O)- may be bonded to any position of the benzene ring (the benzene ring constituting the ring skeleton) to which the bond is attached.
  • the aromatic compound represented by general formula (a) has a structure represented by the following general formula (a1).
  • R 1 to R 8 , Cy 1 , Cy 2 , A 1 , L 1 and L 2 in general formula (a1) are the same as R 1 to R 8 , Cy 1 , Cy 2 , A 1 , L 1 and L 2 in general formula (a), respectively.
  • R 1 to R 8 , Cy 1 , Cy 2 , A 1 , L 1 and L 2 in general formula (a1) the corresponding descriptions in general formula (a) can be referred to.
  • Cy 3 -L 3 -C( ⁇ O)-X 3 - and Cy 4 -L 4 -C( ⁇ O)-X 4 - may be bonded to any position of the benzene ring (the benzene ring constituting the ring skeleton) to which they are bonded.
  • the aromatic compound represented by general formula (b) has a structure represented by the following general formula (b1):
  • R 1 to R 16 , Cy 3 , Cy 4 , A 2 , L 3 and L 4 in general formula (b1) are the same as R 1 to R 16 , Cy 3 , Cy 4 , A 2 , L 3 and L 4 in general formula (b), respectively.
  • R 1 to R 16 , Cy 3 , Cy 4 , A 2 , L 3 and L 4 in general formula (a1) the corresponding descriptions in general formula (b) can be referred to.
  • Compound group 1 represented by general formula (a) can be given as an example of the compound group of the present invention.
  • Compound group 1 includes compound group 1a in which A 1 is a substituted or unsubstituted alkanediyl group and Cy 1 and Cy 2 are substituted or unsubstituted cycloalkyl groups, compound group 1b in which A 1 is a substituted or unsubstituted cycloalkanediyl group and Cy 1 and Cy 2 are substituted or unsubstituted cycloalkyl groups, compound group 1c in which A 1 is a substituted or unsubstituted fluorenediyl group and Cy 1 and Cy 2 are substituted or unsubstituted cycloalkyl groups, compound group 1d in which A 1 is a substituted or unsubstituted alkanediyl group and Cy 1 and Cy 2 are substituted or unsubstituted monovalent aromatic hydrocarbon groups, compound group 1e in which A 1 is a substitute
  • Each of compound groups 1a to 1i may further satisfy at least one of the following additional conditions.
  • One of the additional conditions is that A 1 is an unsubstituted alkanediyl group, an unsubstituted cycloalkanediyl group, or an unsubstituted fluorenediyl group.
  • One of the additional conditions is that Cy 1 and Cy 2 are unsubstituted cycloalkyl groups, unsubstituted monovalent aromatic hydrocarbon groups, or unsubstituted alkyl groups.
  • One of the additional conditions is that Cy 1 and Cy 2 are the same.
  • One of the additional conditions is a condition described in any one of the above groups listed as being included in general formula (a) and general formula (a1).
  • Compound group 2 represented by general formula (b) can be shown as a compound group of the present invention.
  • Compound group 2 includes compound group 2a in which A 2 is a substituted or unsubstituted alkanediyl group and Cy 3 and Cy 4 are substituted or unsubstituted cycloalkyl groups, compound group 2b in which A 2 is a substituted or unsubstituted cycloalkanediyl group and Cy 3 and Cy 4 are substituted or unsubstituted cycloalkyl groups, compound group 2c in which A 2 is a substituted or unsubstituted fluorenediyl group and Cy 3 and Cy 4 are substituted or unsubstituted cycloalkyl groups, compound group 2d in which A 2 is a substituted or unsubstituted alkanediyl group and Cy 3 and Cy 4 are substituted or unsubstituted monovalent aromatic hydrocarbon groups, compound group 2e in which A 2 is a substituted or
  • Each of compound groups 2a to 2i may further satisfy at least one of the following additional conditions.
  • One of the additional conditions is that A 2 is an unsubstituted alkanediyl group, an unsubstituted cycloalkanediyl group, or an unsubstituted fluorenediyl group.
  • One of the additional conditions is that Cy 3 and Cy 4 are unsubstituted cycloalkyl groups, unsubstituted monovalent aromatic hydrocarbon groups, or unsubstituted alkyl groups.
  • One of the additional conditions is that Cy 3 and Cy 4 are the same.
  • One of the additional conditions is a condition described in any one of the above groups listed as being included in general formula (b) and general formula (b1).
  • aromatic compounds represented by general formula (a) or general formula (b) are given. However, the aromatic compounds represented by general formula (a) or general formula (b) that can be used in the present invention should not be interpreted as being limited to these specific examples.
  • the aromatic compound represented by the general formula (a) or (b) is a novel compound.
  • the aromatic compound represented by the general formula (a) or (b) can be synthesized by using a known reaction, such as a reaction between an acid chloride and an amine or a reaction between an acid chloride and a hydroxyl compound.
  • a known reaction such as a reaction between an acid chloride and an amine or a reaction between an acid chloride and a hydroxyl compound.
  • the method for producing the aromatic compound represented by general formula (a) or general formula (b) is not particularly limited.
  • the aromatic compound can be purified by a known method used for purifying organic compounds, such as purification by column chromatography, recrystallization or crystallization using a solvent, or sublimation purification.
  • the compound can be identified by NMR analysis, mass spectrum analysis, etc.
  • the melting point is an index of vapor deposition property
  • the glass transition point (Tg) is an index of stability of the thin film state
  • the refractive index is an index of improvement of light extraction efficiency.
  • the melting point and glass transition point (Tg) of the aromatic compound of the present invention can be measured, for example, using a powder with a high-sensitivity differential scanning calorimeter (DSC3100SA, manufactured by Bruker AXS).
  • DSC3100SA high-sensitivity differential scanning calorimeter
  • the refractive index and extinction coefficient of the aromatic compound of the present invention can be measured by preparing an 80 nm thin film on a silicon substrate and using a spectrometer (F10-RT-UV, manufactured by Filmetrics).
  • the aromatic compound represented by general formula (a) or general formula (b) of the present invention has a characteristic of low refractive index.
  • a capping layer formed by stacking a first capping layer (low refractive index layer) containing this aromatic compound and a second capping layer (high refractive index layer) having a higher refractive index than the first capping layer is arranged at a position outside the electrode of the light extraction side of the organic EL element (opposite to the light emitting layer side of the electrode), so that the first capping layer is on the electrode side, and the light extraction efficiency is improved by the effective light interference effect of the capping layer, and high luminous efficiency can be realized.
  • the aromatic compound represented by general formula (a) or general formula (b) has a melting point suitable for deposition, and has a high glass transition temperature and is stable in a thin film state.
  • capping layer in this specification means a layer disposed on the opposite side (outside) of at least one of a pair of electrodes from the light-emitting layer in an organic EL element in which a light-emitting layer is disposed between a pair of electrodes.
  • the capping layer containing an aromatic compound represented by general formula (a) or general formula (b) may be disposed only on the outside of one of the pair of electrodes, or may be disposed on the outside of both electrodes.
  • an organic layer such as a charge transport layer may be disposed between the light-emitting layer and each electrode of the organic EL element to which the capping layer is applied.
  • the organic electroluminescence device (organic EL device) of the present invention has at least an anode electrode, a hole transport layer, a light emitting layer, an electron transport layer, a cathode electrode and a capping layer in this order, and is characterized in that the capping layer contains an aromatic compound represented by general formula (a) or general formula (b).
  • aromatic compound represented by general formula (a) or general formula (b) please refer to the description in the above section "Aromatic compound represented by general formula (a) or general formula (b)".
  • the capping layer is constructed by laminating a first capping layer (low refractive index layer) containing an aromatic compound represented by general formula (a) or general formula (b) and a second capping layer (high refractive index layer) having a higher refractive index than the first capping layer.
  • the second capping layer having a high refractive index improves the light extraction efficiency of the organic EL element, and furthermore, the high reflectance at the interface between the second capping layer and the first capping layer causes a light interference effect, so that the second capping layer is more effective in improving the light extraction efficiency.
  • the capping layer is preferably disposed such that the first capping layer is disposed on the electrode side (the second capping layer is disposed on the outer side) of the first capping layer and the second capping layer.
  • the organic EL element has at least an anode electrode, a hole transport layer, an emitting layer, an electron transport layer, a cathode electrode, the first capping layer, and the second capping layer in this order.
  • the structure of the organic EL element of the present invention may be, for example, a top-emission light-emitting element that is composed of an anode, hole transport layer, light-emitting layer, electron transport layer, cathode, and capping layer in that order on a substrate made of glass or the like; a hole injection layer between the anode and hole transport layer; an electron blocking layer between the hole transport layer and light-emitting layer; a hole blocking layer between the light-emitting layer and electron transport layer; or an electron injection layer between the electron transport layer and cathode.
  • a structure that combines the hole injection layer and hole transport layer for example, a structure that combines the hole injection layer and hole transport layer, a structure that combines the hole transport layer and electron blocking layer, a structure that combines the hole blocking layer and electron transport layer, or a structure that combines the electron transport layer and electron injection layer are also possible. It is also possible to have a structure in which two or more organic layers having the same function are laminated, such as a structure in which two hole transport layers are laminated, a structure in which two light emitting layers are laminated, a structure in which two electron transport layers are laminated, or a structure in which two capping layers are laminated.
  • the total thickness of each layer of the organic EL element is preferably about 200 nm to 750 nm, more preferably about 350 nm to 600 nm.
  • the thickness of the capping layer is, for example, preferably 30 nm to 120 nm, more preferably 40 nm to 80 nm. In this case, good light extraction efficiency is obtained.
  • the thickness of the capping layer can be appropriately changed depending on the type of light emitting material used in the light emitting element, the thickness of the organic EL element other than the capping layer, etc. Each member and each layer constituting the organic EL element will be described below.
  • an electrode material having a large work function such as ITO (indium tin oxide) or gold, is used.
  • arylamine compound having three or more triphenylamine structures in a molecule, and having a structure in which these triphenylamine structures are linked by a single bond or a divalent group not containing a heteroatom, can be mentioned.
  • arylamine compound for example, a starburst type triphenylamine derivative, various triphenylamine tetramers, and other materials can be mentioned.
  • a porphyrin compound represented by copper phthalocyanine, an acceptor heterocyclic compound such as hexacyanoazatriphenylene, or a coating type polymer material can be used as the material of the hole injection layer.
  • the hole injection layer may be composed of a single layer formed by solely forming a film of these hole injection materials, or may be composed of a mixed layer formed by mixing two or more materials.
  • the hole injection layer may have a single layer structure, a laminate structure of layers formed by solely forming a film or layers formed by mixing, or a laminate structure of layers formed by solely forming a film and layers formed by mixing. These materials can be formed into a thin film by known methods such as a vapor deposition method, a spin coating method, and an ink jet method.
  • benzidine derivatives such as N,N'-diphenyl-N,N'-di(m-tolyl)benzidine (hereinafter abbreviated as TPD), N,N'-diphenyl-N,N'-di( ⁇ -naphthyl)benzidine (hereinafter abbreviated as NPD), N,N,N',N'-tetrabiphenylylbenzidine, 1,1-bis[4-(di-4-tolylamino)phenyl]cyclohexane (hereinafter abbreviated as TAPC), etc. can be used.
  • TPD N,N'-diphenyl-N,N'-di( ⁇ -naphthyl)benzidine
  • NPD N,N,N',N'-tetrabiphenylylbenzidine
  • TAPC 1,1-bis[4-(di-4-tolylamino)phenyl]cyclohexane
  • an arylamine compound having two triphenylamine structures in the molecule and having a structure in which these triphenylamine structures are linked by a single bond or a divalent group not containing a hetero atom, such as N,N,N',N'-tetrabiphenylylbenzidine.
  • an arylamine compound having three or more triphenylamine structures in a molecule and these triphenylamine structures are linked by a single bond or a divalent group not containing a heteroatom, such as various triphenylamine trimers and tetramers.
  • the hole transport layer may be composed of a single layer formed by solely depositing one of these hole transport materials, or a mixed layer formed by mixing two or more materials.
  • the hole transport layer may have a single layer structure, a laminate structure in which layers formed by solely depositing or layers formed by mixing are laminated, or a laminate structure in which a layer formed by solely depositing and a layer formed by mixing are laminated.
  • a coating type polymer material such as poly(3,4-ethylenedioxythiophene) (hereinafter abbreviated as PEDOT)/poly(styrenesulfonate) (hereinafter abbreviated as PSS) can be used as the hole injection/transport layer.
  • PEDOT poly(3,4-ethylenedioxythiophene)
  • PSS poly(styrenesulfonate)
  • materials that are normally used in these layers can be further doped with a p-type dopant such as trisbromophenylamine hexachloroantimony or radialene derivatives, or polymer compounds that contain the structure of a benzidine derivative such as TPD as a partial structure.
  • a p-type dopant such as trisbromophenylamine hexachloroantimony or radialene derivatives
  • polymer compounds that contain the structure of a benzidine derivative such as TPD as a partial structure.
  • the organic EL device of the present invention may have an electron blocking layer between the light emitting layer and the hole transport layer.
  • a compound having an electron blocking effect can be used, such as a carbazole derivative such as 4,4',4''-tri(N-carbazolyl)triphenylamine (hereinafter abbreviated as TCTA), 9,9-bis[4-(carbazol-9-yl)phenyl]fluorene, 1,3-bis(carbazol-9-yl)benzene (hereinafter abbreviated as mCP), or 2,2-bis(4-carbazol-9-yl-phenyl)adamantane (hereinafter abbreviated as Ad-Cz), or a compound having a triphenylsilyl group and a triarylamine structure, such as 9-[4-(carbazol-9-yl)phenyl]-9-[4-(triphenylsilyl)phenyl
  • TCTA 4,4',4''-tri
  • the electron blocking layer may be a single layer formed by depositing one of these electron blocking materials alone, or may be a mixed layer formed by mixing two or more materials.
  • the electron blocking layer may have a single layer structure, a laminate structure formed by laminating layers formed by depositing layers formed by depositing layers formed by mixing, or a laminate structure formed by depositing layers formed by depositing layers formed by mixing layers formed by depositing ...
  • Light-emitting layer As the material of the light-emitting layer of the organic EL element of the present invention, in addition to metal complexes of quinolinol derivatives such as tris(8-quinolinolato)aluminum (Alq 3 ), various light-emitting materials such as metal complexes, anthracene derivatives, bisstyrylbenzene derivatives, pyrene derivatives, oxazole derivatives, polyparaphenylenevinylene derivatives, etc. can be used.
  • the light-emitting layer may be composed of a host material and a dopant material, and anthracene derivatives are preferably used as the host material.
  • heterocyclic compounds having an indole ring as a partial structure of a condensed ring in addition to the above light-emitting materials, heterocyclic compounds having a carbazole ring as a partial structure of a condensed ring, carbazole derivatives, thiazole derivatives, benzimidazole derivatives, polydialkylfluorene derivatives, etc. can be used.
  • dopant material quinacridone, coumarin, rubrene, perylene and derivatives thereof, benzopyran derivatives, rhodamine derivatives, aminostyryl derivatives, etc. can be used, and it is particularly preferable to use a green light-emitting material.
  • the light-emitting layer may be composed of a single layer formed by solely using one of the above light-emitting materials, or may be composed of a mixed layer formed by mixing two or more materials (for example, two or more light-emitting materials, or one or more host materials and one or more dopant materials).
  • the light-emitting layer may have a single layer structure, a laminate structure in which layers formed by solely using the light-emitting materials or layers formed by mixing the light-emitting materials are laminated, or a laminate structure in which a layer formed by solely using the light-emitting materials and a layer formed by mixing the light-emitting materials are laminated.
  • a phosphorescent emitter As the phosphorescent emitter, a phosphorescent emitter of a metal complex such as iridium or platinum can be used.
  • a green phosphorescent emitter such as Ir(ppy) 3 (tris(2-phenylpyridinato)iridium(III)
  • a blue phosphorescent emitter such as FIrpic (bis[2-(4,6-difluorophenyl)pyridinato-C2,N](picolinato)iridium(III)) or FIr6 (bis(2,4-difluorophenylpyridinato)tetrakis(1-pyrazolyl)borateiridium(III))
  • a red phosphorescent emitter such as Btp 2 Ir(acac) (bis(2-benzo[b]thiophen-2-yl-pyridine)(acetylacetonato)irid
  • the light-emitting layer may be composed of only these phosphorescent emitters, or may be composed of a host material and a phosphorescent emitter (for example, a co-deposition film of a host material and a phosphorescent emitter).
  • a host material and a phosphorescent emitter for example, a co-deposition film of a host material and a phosphorescent emitter.
  • carbazole derivatives such as 4,4'-di(N-carbazolyl)biphenyl (hereinafter abbreviated as CBP), TCTA, and mCP can be used.
  • UGH2 p-bis(triphenylsilyl)benzene
  • TPBI 2,2',2''-(1,3,5-phenylene)-tris(1-phenyl-1H-benzimidazole)
  • UGH2 p-bis(triphenylsilyl)benzene
  • TPBI 2,2',2''-(1,3,5-phenylene)-tris(1-phenyl-1H-benzimidazole)
  • the amount of phosphorescent material doped into the host material is preferably in the range of 1 to 30 weight percent of the amount of the light-emitting layer to avoid concentration quenching.
  • luminescent material materials that emit delayed fluorescence as the luminescent material. These materials can be formed into thin films by known methods such as deposition, spin coating, and inkjet printing.
  • the organic EL element of the present invention may have a hole blocking layer between the light emitting layer and the electron transport layer.
  • a hole blocking layer compounds having a hole blocking effect, such as phenanthroline derivatives such as bathocuproine (hereinafter abbreviated as BCP), metal complexes of quinolinol derivatives such as aluminum (III) bis(2-methyl-8-quinolinato)-4-phenylphenolate (hereinafter abbreviated as BAlq), various rare earth complexes, triazole derivatives, triazine derivatives, pyrimidine derivatives, oxadiazole derivatives, and benzoazole derivatives, can be used. These materials may also serve as the material of the electron transport layer.
  • BCP bathocuproine
  • BAlq metal complexes of quinolinol derivatives
  • BAlq aluminum (III) bis(2-methyl-8-quinolinato)-4-phenylphenolate
  • BAlq aluminum (III) bis(2-methyl-8-quinolinato)-4-
  • the hole blocking layer may be composed of a single layer formed by depositing one of these electron blocking materials alone, or may be composed of a mixed layer formed by mixing two or more materials.
  • the hole blocking layer may have a single layer structure, a laminate structure in which layers formed by depositing alone or layers formed by mixing are laminated, or a laminate structure in which a layer formed by depositing alone and a layer formed by mixing are laminated. These materials can be used to form thin films by known methods such as vapor deposition, spin coating, and ink jet printing.
  • Electrode As the material of the electron transport layer of the organic EL element of the present invention, in addition to metal complexes of quinolinol derivatives such as Alq3 and BAlq, various metal complexes, triazole derivatives, triazine derivatives, pyrimidine derivatives, oxadiazole derivatives, pyridine derivatives, benzimidazole derivatives, benzoazole derivatives, thiadiazole derivatives, anthracene derivatives, carbodiimide derivatives, quinoxaline derivatives, pyridoindole derivatives, phenanthroline derivatives, silole derivatives, etc. can be used.
  • quinolinol derivatives such as Alq3 and BAlq
  • the electron transport layer may be composed of a single layer formed by solely depositing one of these electron transport materials, or may be composed of a mixed layer formed by mixing two or more materials.
  • the electron transport layer may be composed of a single layer, a laminated structure formed by laminating layers formed by solely depositing layers or layers formed by mixing layers, or a laminated structure formed by laminating layers formed by solely depositing layers and layers formed by mixing layers. These materials can be formed into thin films by known methods such as vapor deposition, spin coating, inkjet, etc.
  • 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
  • metal oxides such as aluminum oxide
  • metals such as ytterbium (Yb), samarium (Sm), calcium (Ca), strontium (Sr), and cesium (Cs)
  • Yb ytterbium
  • Sm samarium
  • Ca calcium
  • Cs cesium
  • materials that are normally used for the electron injection layer or electron transport layer can be doped with an n-type metal dopant such as cesium.
  • the cathode material for the organic EL element of the present invention may be an electrode material with a low work function such as aluminum, an alloy with an even lower work function such as a magnesium-silver alloy, a magnesium-calcium alloy, a magnesium-indium alloy, an aluminum-magnesium alloy, or a conductive transparent material such as ITO (indium tin oxide), IZO (indium zinc oxide), etc.
  • the metal or alloy is formed to a thickness of about 10 to 200 nm to form a semitransparent cathode electrode.
  • the organic EL element of the present invention contains an aromatic compound represented by general formula (a) or general formula (b) in the capping layer.
  • the capping layer preferably has a laminated structure in which a first capping layer containing an aromatic compound represented by general formula (a) or general formula (b) and a second capping layer having a higher refractive index than the first capping layer are laminated, and is preferably a two-layer structure of a first capping layer and a second capping layer.
  • the capping layer having a laminated structure is preferably arranged so that the first capping layer is adjacent to the cathode electrode.
  • the capping layer and the first capping layer may contain only one type of aromatic compound represented by general formula (a), or may contain two or more types.
  • the capping layer and the first capping layer may contain only one type of aromatic compound represented by general formula (b), or may contain two or more types.
  • the capping layer and the first capping layer may contain only one of the aromatic compound represented by general formula (a) and the aromatic compound represented by general formula (b), or may contain both.
  • the second capping layer is made of a material having a refractive index higher than that of the aromatic compound used in the first capping layer, and may be made of an arylamine compound or the like (see, for example, Patent Documents 4 and 5).
  • the refractive index of the material constituting the second capping layer is preferably at least 0.15 higher than the refractive index of the adjacent first capping layer, more preferably at least 0.20 higher, and even more preferably at least 0.30 higher.
  • the first capping layer and the second capping layer may each be a single layer formed from one of the above-mentioned capping layer materials, or a mixed layer formed from a mixture of two or more materials. These materials can be formed into thin films by known methods such as deposition, spin coating, and inkjet printing.
  • the total thickness of the first capping layer and the second capping layer is, for example, preferably 30 nm to 120 nm, and more preferably 40 nm to 80 nm.
  • the ratio of the thickness of the first capping layer to the second capping layer is preferably 1:99 to 99:1, more preferably 90:10 to 90:10, and even more preferably 20:80 to 80:20. In this case, good light extraction efficiency is obtained.
  • the thicknesses of the first capping layer and the second capping layer can be changed as appropriate depending on the type of light-emitting material used in the light-emitting element, the thickness of the organic EL element other than the capping layer, etc.
  • the present invention has been described using an organic EL element with a top emission structure as an example, but the organic EL element to which the present invention is applied is not limited to this, and may be an organic EL element with a bottom emission structure or an organic EL element with a dual emission structure that emits light from both the top and bottom.
  • the above description of the organic EL element can be referred to.
  • the electrode in the direction in which light is extracted from the light emitting element to the outside must be transparent or semitransparent.
  • the electrode on the substrate side is preferably transparent or semitransparent, and in the dual emission structure, the electrodes on both sides are preferably transparent or semitransparent.
  • the capping layer can be provided between the electrode on the substrate side and the substrate, and in the dual emission structure, it can be provided between the electrode on the substrate side and the substrate, and on the outside of the electrode on the opposite side to the substrate, or it can be provided on only one of them.
  • the electronic device and electronic element of the present invention have a pair of electrodes and at least one organic layer, and at least one of the organic layers contains an aromatic compound represented by general formula (a) or general formula (b).
  • aromatic compound represented by general formula (a) or general formula (b) please refer to the description in the above section "Aromatic compound represented by general formula (a) or general formula (b)".
  • the electronic device include a display device or a light-emitting device having an organic EL element, as well as an electrophotographic photoreceptor, an image sensor, a photoelectric conversion element, a solar cell, etc.
  • Examples of the display device include a display component such as an organic EL panel module, a television, a mobile phone, a tablet, a personal computer, etc.
  • the light-emitting device include lighting or a vehicle lamp, etc.
  • Example 1 Synthesis of compound (1-7) 5.0 g of 2,2'-bis(4-aminophenyl)hexafluoropropane, 6.4 g of triethylamine, and 100 mL of tetrahydrofuran were added to a reaction vessel, and the mixture was stirred for 30 minutes in an ice bath. A mixture of 6.3 g of 1-adamantanecarbonyl chloride and 20 mL of tetrahydrofuran was added dropwise to the reaction vessel over 30 minutes and stirred for 3 hours. The mixture was warmed to room temperature and stirred overnight, and then 100 mL of water and 300 mL of dichloromethane were added to perform an extraction operation.
  • Example 3 Synthesis of compound (1-10) 5.1 g of 1-adamantamine hydrochloride, 5.5 g of triethylamine, and 100 mL of tetrahydrofuran were added to a reaction vessel, and the mixture was stirred for 30 minutes in an ice bath. A mixture of 5.5 g of 4,4'-[2,2,2-trifluoro-1-(trifluoromethyl)ethylidene]bis[benzoyl chloride] and 20 mL of tetrahydrofuran was added dropwise to the reaction vessel over 30 minutes, and the mixture was stirred for 3 hours.
  • Example 9 Measurement of glass transition point and melting point
  • the glass transition points of the aromatic compounds obtained in Examples 1 to 8 were measured using a high-sensitivity differential scanning calorimeter (DSC3100SA, manufactured by Bruker AXS). The measurement results are summarized in Table 1.
  • Example 10 Measurement of refractive index Using the aromatic compounds obtained in Examples 1 to 8, a vapor-deposited film having a thickness of 80 nm was prepared on a silicon substrate, and the refractive index n was measured at room temperature using a spectrometer (F10-RT-UV, manufactured by Filmetrics). In addition, the refractive index n was similarly measured for the compound (CPL-1) used as the high refractive index capping material and Alq3 used as the comparative compound in the following organic EL device preparation examples. The measurement results are summarized in Table 2.
  • the refractive index of the aromatic compound of the present invention is 1.70 or less, which is smaller than the refractive indexes of Alq3 and compound (CPL-1).
  • Example 11 Preparation of Organic EL Device Using Compound (1-7)
  • a reflective ITO electrode was formed in advance as a transparent anode 2 on a glass substrate 1, and a hole injection layer 3, a hole transport layer 4, an emitting layer 5, an electron transport layer 6, an electron injection layer 7, a cathode 8, a first capping layer 9, and a second capping layer 10 were deposited in this order by vapor deposition on the reflective ITO electrode as a transparent anode 2 on a glass substrate 1 to prepare an organic EL device.
  • a glass substrate 1 on which a 50 nm thick ITO film, a 100 nm thick silver alloy reflective film, and a 5 nm thick ITO film were formed in this order was ultrasonically cleaned in isopropyl alcohol for 20 minutes, and then dried on a hot plate heated to 250°C for 10 minutes. After that, a UV ozone treatment was performed for 2 minutes, and the glass substrate with ITO was attached in a vacuum deposition machine and the pressure was reduced to 0.001 Pa or less.
  • a hole transport layer 4 was formed of a compound (3-1) of the following structural formula to a thickness of 140 nm.
  • lithium fluoride was formed as an electron injection layer 7 with a thickness of 1 nm.
  • a magnesium silver alloy was formed on this electron injection layer 7 as a cathode 8 to a thickness of 12 nm.
  • a first capping layer 9 was formed on the cathode 8 using the compound (1-7) of Example 1 to a thickness of 30 nm, and finally a second capping layer 10 was formed using the compound (CPL-1) to a thickness of 30 nm.
  • the light-emitting characteristics of the fabricated organic EL element were measured by applying a direct current voltage in the air at room temperature. The measurement results are summarized in Table 3.
  • Example 12 Preparation of Organic EL Device Using Compound (1-8) An organic EL device was prepared under the same conditions as in Example 11, except that the material for the first capping layer 9 was compound (1-8) instead of compound (1-7), and the first capping layer 9 was formed to a thickness of 30 nm.
  • the light-emitting characteristics of the prepared organic EL device were measured by applying a direct current voltage in the air at room temperature. The measurement results are summarized in Table 3.
  • Example 13 Preparation of Organic EL Device Using Compound (1-10) An organic EL device was prepared under the same conditions as in Example 11, except that the material for the first capping layer 9 was compound (1-10) instead of compound (1-7), and the first capping layer 9 was formed to a thickness of 30 nm.
  • the light-emitting characteristics of the prepared organic EL device were measured by applying a direct current voltage in the air at room temperature. The measurement results are summarized in Table 3.
  • Example 14 Preparation of Organic EL Device Using Compound (1-19) An organic EL device was prepared under the same conditions as in Example 11, except that compound (1-19) was used instead of compound (1-7) as the material for the first capping layer 9, and the first capping layer 9 was formed to a thickness of 30 nm. A direct current voltage was applied to the prepared organic EL device in the air at room temperature to measure the luminescence characteristics. The measurement results are summarized in Table 3.
  • Example 15 Preparation of Organic EL Device Using Compound (1-2)
  • An organic EL device was prepared under the same conditions as in Example 11, except that the material for the first capping layer 9 was compound (1-2) instead of compound (1-7), and the first capping layer 9 was formed to a thickness of 30 nm.
  • the light-emitting characteristics of the prepared organic EL device were measured by applying a direct current voltage in the air at room temperature. The measurement results are summarized in Table 3.
  • Example 16 Preparation of Organic EL Device Using Compound (1-20)
  • An organic EL device was prepared under the same conditions as in Example 11, except that the material for the first capping layer 9 was compound (1-20) instead of compound (1-7), and the first capping layer 9 was formed to a thickness of 30 nm.
  • the light-emitting characteristics of the prepared organic EL device were measured by applying a direct current voltage in the air at room temperature. The measurement results are summarized in Table 3.
  • Example 17 Preparation of Organic EL Device Using Compound (1-193) An organic EL device was prepared under the same conditions as in Example 11, except that compound (1-193) was used instead of compound (1-7) as the material for first capping layer 9, and first capping layer 9 was formed to a thickness of 30 nm. A direct current voltage was applied to the prepared organic EL device in the air at room temperature to measure the luminescence characteristics. The measurement results are summarized in Table 3.
  • Example 18 An organic EL element was prepared under the same conditions as in Example 11, except that the material of the first capping layer 9 was compound (1-194) instead of compound (1-7), and the first capping layer 9 was formed to a thickness of 30 nm.
  • the light-emitting characteristics of the prepared organic EL element were measured by applying a direct current voltage in the air at room temperature. The measurement results are summarized in Table 3.
  • Comparative Example 1 Preparation of organic EL element using Alq3 An organic EL element was prepared under the same conditions as in Example 7, except that Alq3 was used instead of compound (1-13) as the material for the first capping layer 9, and the first capping layer was formed to a thickness of 30 nm. The light-emitting characteristics of the prepared organic EL element were measured by applying a direct current voltage in the air at room temperature. The measurement results are summarized in Table 3.
  • Comparative Example 2 Preparation of an organic EL element having a single-layered capping layer An organic EL element was prepared under the same conditions as in Example 7, except that instead of the capping layer consisting of the first capping layer 9 and the second capping layer 10, a single-layered capping layer was formed by forming the compound (CPL-1) to a thickness of 60 nm. The light-emitting characteristics of the prepared organic EL element were measured by applying a direct current voltage in the air at room temperature. The measurement results are summarized in Table 3.
  • the device lifetimes of the organic EL devices prepared in Examples 11 to 18 and Comparative Examples 1 and 2 were measured and the results are summarized in Table 3.
  • the device lifetimes were expressed as the time required for the luminance to decay to 95% of the initial luminance when driven at a constant current of 10 mA/ cm2 .
  • the driving voltage at a current density of 10 mA/ cm2 was almost the same for the elements of Comparative Example 1 and Comparative Example 2 and the elements of Examples 11 to 18.
  • the luminance, luminous efficiency, power efficiency, and lifespan of the elements of Examples 11 to 18 were all improved compared to the elements of Comparative Example 1 and Comparative Example 2. This shows that the light extraction efficiency can be significantly improved by providing a stacked structure of a first capping layer containing the aromatic compound of the present invention and a second capping layer having a high refractive index as a capping layer.
  • An organic EL element having a capping layer containing the aromatic compound of the present invention particularly an organic EL element in which a first capping layer containing the aromatic compound of the present invention is laminated with a second capping layer having a high refractive index, can achieve high efficiency and can be effectively used in various devices that use light-emitting elements. Therefore, the present invention has a high industrial applicability.

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