WO2022173022A1 - 化合物および該化合物を用いた有機エレクトロルミネッセンス素子 - Google Patents

化合物および該化合物を用いた有機エレクトロルミネッセンス素子 Download PDF

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WO2022173022A1
WO2022173022A1 PCT/JP2022/005500 JP2022005500W WO2022173022A1 WO 2022173022 A1 WO2022173022 A1 WO 2022173022A1 JP 2022005500 W JP2022005500 W JP 2022005500W WO 2022173022 A1 WO2022173022 A1 WO 2022173022A1
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substituted
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French (fr)
Japanese (ja)
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絵里子 千葉
剛史 山本
幸喜 加瀬
雄太 平山
秀一 林
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Hodogaya Chemical Co Ltd
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Hodogaya Chemical Co Ltd
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Priority to US18/273,421 priority Critical patent/US20240116914A1/en
Priority to KR1020237022499A priority patent/KR20230147044A/ko
Priority to CN202280011037.7A priority patent/CN116848077A/zh
Priority to JP2022580697A priority patent/JP7801261B2/ja
Publication of WO2022173022A1 publication Critical patent/WO2022173022A1/ja
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Definitions

  • the present invention relates to compounds suitable for self-luminous electronic devices suitable for various display devices, particularly compounds suitable for organic electroluminescence devices (hereinafter abbreviated as organic EL devices), and organic EL devices using the compounds. .
  • organic EL devices organic electroluminescence devices
  • Non-Patent Document 1 In an electroluminescence device provided with an electron transport layer, an electron injection layer and a cathode, a light emitting device having a bottom emission structure in which light is emitted from the bottom has come to achieve high efficiency and durability. (For example, see Non-Patent Document 1)
  • a metal with a high work function is used for the anode and light is emitted from above.
  • the bottom emission structure in which light is extracted from the bottom of the pixel circuit, the area of the light emitting part is limited. Therefore, there is an advantage that the light emitting portion can be widened.
  • a semi-transparent electrode such as LiF/Al/Ag (see, for example, Non-Patent Document 2), Ca/Mg (see, for example, Non-Patent Document 3), or LiF/MgAg is used for the cathode.
  • Alq3 tris(8-hydroxyquinoline)aluminum (hereinafter abbreviated as Alq3) as a capping layer for adjusting the refractive index (see, for example, Non-Patent Document 2).
  • Alq3 is known as an organic EL material that is generally used as a green light-emitting material or an electron transport material. There was a problem of lower extraction efficiency.
  • the present invention is a compound represented by the following general formula (1) and an organic EL device using the compound, specifically as follows.
  • B is a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted aryl represents an oxy group.
  • Ar 1 and Ar 2 may be the same or different, and may be a substituted or unsubstituted divalent aromatic hydrocarbon group, a substituted or unsubstituted divalent aromatic heterocyclic group, a substituted or unsubstituted It represents a divalent group of a substituted condensed polycyclic aromatic group or a single bond.
  • A1 and A2 which may be the same or different, represent a monovalent group represented by the following general formula (2).
  • R 1 to R 8 may be the same or different, and have a bonding site, a hydrogen atom, a deuterium atom, a fluorine atom, a chlorine atom, a cyano group, a nitro group, or a substituent.
  • X 1 to X 8 may be the same or different from each other and represent a nitrogen atom or a carbon atom, the number of X 1 to X 8 being nitrogen atoms is 0 to 2, and when they are nitrogen atoms It does not have R 1 -R 8 attached.
  • R 1 to R 8 in formulas (3a), (3b) and (3c) have the same definitions as R 1 to R 8 in formula (2).
  • An organic electroluminescence device 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, wherein the capping layer is the organic thin film described in 4) above. Electroluminescence device.
  • An electronic device having a pair of electrodes and at least one organic layer sandwiched therebetween, wherein the organic layer contains the compound according to any one of 1) to 3) above.
  • unsubstituted in the case of “substituted or unsubstituted” means that a hydrogen atom is not substituted with a substituent.
  • hydrogen atom includes isotopes with different numbers of neutrons, that is, hydrogen and deuterium.
  • the "substituent" in the case of “substituted or unsubstituted” specifically includes a cyano group, a nitro group, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 3 carbon atoms, a substituted or unsubstituted Examples include a substituted phenyl group and a substituted or unsubstituted alkoxy group having 1 to 3 carbon atoms.
  • aromatic hydrocarbon group is specifically Specifically, phenyl, biphenylyl, terphenylyl, naphthyl, anthracenyl, phenanthrenyl, fluorenyl, spirobifluorenyl, indenyl, pyrenyl, perylenyl, fluoranthenyl, triphenylenyl, pyridyl , pyrimidinyl group, triazinyl group, furyl group, pyrrolyl group, thienyl group, quinolyl group, isoquinolyl group,
  • a linear or branched alkyl group having 1 to 6 carbon atoms which may have a substituent having a substituent cycloalkyl group having 5 to 10 carbon atoms which may be substituted”, “linear or branched alkenyl group having 2 to 6 carbon atoms which may have a substituent”, A linear or branched alkyloxy group having 1 to 6 carbon atoms which may be substituted", "a cycloalkyloxy group having 5 to 10 carbon atoms which may have “linear or branched alkyl group having 1 to 6 carbon atoms", “cycloalkyl group having 5 to 10 carbon atoms", “straight chain having 2 to 6 carbon atoms” in "unsubstituted aryloxy group” as a linear or branched alkenyl group", a “linear or branched alkyloxy group having 1 to 6 carbon atoms", a “cycloalkyloxy group having 5 to 10 carbon atoms", or an "aryloxy group
  • substituents in the "cycloalkyl group having 5 to 10 numbers” or “linear or branched alkenyl group having 2 to 6 carbon atoms and optionally having a substituent” include: deuterium atom, cyano group, nitro group; halogen atom such as fluorine atom, chlorine atom, bromine atom and iodine atom; silyl group such as trimethylsilyl group and triphenylsilyl group; carbon atom such as methyl group, ethyl group and propyl group linear or branched alkyl group having 1 to 6 carbon atoms; linear or
  • adjacent benzene rings substituted with these substituents or multiple substituents substituted on the same benzene ring are bonded to each other through a single bond, a substituted or unsubstituted methylene group, an oxygen atom or a sulfur atom. may form a ring.
  • A1 and A2 in general formula (1) are represented by general formula (2) above and are monovalent groups having any one of R 1 to R 8 as a binding site.
  • the group represented by the general formula (2) is preferably a monovalent group represented by the general formula (3a), (3b) or (3c), and is represented by the general formula (3a) or (3c). is more preferred. Also, it is preferred that A1 and A2 are the same.
  • the binding site is R 2 , R 3 , R 8 or R 6 from the viewpoint of refractive index and heat resistance. is preferably From the viewpoint of ease of synthesis, it is preferable that all of R 2 to R 8 that are not binding sites are hydrogen atoms.
  • the binding site is preferably R 2 from the viewpoint of refractive index and heat resistance. From the viewpoint of ease of synthesis, it is preferable that all of R 1 to R 8 that are not bonding sites are hydrogen atoms.
  • Ar 1 and Ar 2 in general formula (1) are preferably each independently selected from a phenylene group, a pyridylene group, a pyrimidinylene group and a single bond from the viewpoint of refractive index and heat resistance.
  • B in general formula (1) is more preferably a substituted or unsubstituted naphthalenyl group, phenanthrenyl group, dibenzofuranyl group, dibenzothiophenyl group, fluorenyl group, carbazolyl group, benzofuranyl group or benzothiophenyl group.
  • the compound represented by the general formula (1) of the present invention preferably has a refractive index of 1.70 or more, particularly preferably 1.85 or more, in the wavelength range of 450 nm to 700 nm.
  • the compound represented by the general formula (1) of the present invention has a high refractive index and a low extinction coefficient in the wavelength range of 450 nm to 750 nm.
  • a capping layer having a refractive index higher than that of the transparent electrode it is possible to obtain an organic EL device capable of greatly improving light extraction efficiency.
  • FIG. 1 shows the structures of compounds (1-1) to (1-12) as examples of the compounds of the present invention.
  • FIG. 1 shows the structures of compounds (1-13) to (1-24) as examples of the compounds of the present invention.
  • FIG. 1 shows the structures of compounds (1-25) to (1-36) as examples of the compounds of the present invention.
  • FIG. 1 shows the structures of compounds (1-37) to (1-45) as examples of the compounds of the present invention.
  • FIG. 1 shows the structures of compounds (1-46) to (1-50) as examples of the compounds of the present invention. It is a figure which shows an example of a structure of the organic EL element of this invention.
  • the compound represented by the general formula (1) of the present invention is a novel compound, it can be synthesized according to a known method using a cross-coupling reaction or the like.
  • the purification method of the compound represented by the general formula (1) of the present invention is not particularly limited, and purification by column chromatography, adsorption purification by silica gel, activated carbon or activated clay, recrystallization or crystallization with a solvent, sublimation.
  • Known methods used for purification of organic compounds, such as purification can be mentioned.
  • Identification of compounds can be performed by NMR analysis. As physical properties, it is preferable to measure the melting point, glass transition point (Tg), and refractive index.
  • the melting point and glass transition point (Tg) were measured using a powder compound with a high-sensitivity differential scanning calorimeter (DSC3100SA, manufactured by Bruker AXS).
  • the refractive index was measured by preparing a thin film of 80 nm on a silicon substrate and using a spectrometer (F10-RT-UV manufactured by Filmetrics).
  • an anode, a hole-transporting layer, a light-emitting layer, an electron-transporting layer, a cathode and a capping layer are sequentially formed on a glass substrate. Further, a hole injection layer is provided between the anode and the hole transport layer, an electron blocking layer is provided between the hole transport layer and the light emitting layer, and a hole blocking layer is provided between the light emitting layer and the electron transport layer. and those having an electron injection layer between the electron transport layer and the cathode.
  • one organic layer can serve several roles, for example, a combination of a hole-injection layer and a hole-transport layer, a combination of a hole-transport layer and an electron-blocking layer. It is also possible to use a structure that serves as both a hole-blocking layer and an electron-transporting layer, a structure that serves as both an electron-transporting layer and an electron-injecting layer, and the like. In addition, it is also possible to have a structure in which two or more organic layers having the same function are stacked, such as a structure in which two hole transport layers are stacked, a structure in which two light emitting layers are stacked, and a structure in which two electron transport layers are stacked. A laminated structure, a structure in which two capping layers are laminated, and the like are also possible.
  • 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 film 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 can be obtained.
  • the thickness of the capping layer can be appropriately changed according to the type of light-emitting material used in the light-emitting element, the thickness of the organic EL element other than the capping layer, and the like.
  • an electrode material with a large work function such as ITO or gold is used.
  • an arylamine compound having a structure in which three or more triphenylamine structures are linked in the molecule with a single bond or a divalent group containing no heteroatoms such as Starburst.
  • arylamine compounds such as various triphenylamine tetramers, porphyrin compounds represented by copper phthalocyanine, acceptor heterocyclic compounds such as hexacyanoazatriphenylene, and coating-type polymer materials can be used.
  • NPD N,N'-diphenyl-N,N'-di(m-tolyl)benzidine
  • NPD N,N'-diphenyl-N
  • benzidine derivatives such as N'-di( ⁇ -naphthyl)benzidine (hereinafter abbreviated as NPD) and N,N,N',N'-tetrabiphenylylbenzidine, 1,1-bis[4-(di-4 -tolylamino)phenyl]cyclohexane
  • TAPC 1,1-bis[4-(di-4 -tolylamino)phenyl]cyclohexane
  • an arylamine compound having a structure in which two triphenylamine structures are linked in the molecule by a single bond or a divalent group that does not contain a heteroatom such as N , N,N',N'-tetrabiphenylylbenzidine and the like can be used.
  • arylamine compounds having a structure in which three or more triphenylamine structures are linked in the molecule by a single bond or a divalent group containing no heteroatoms such as various triphenylamine trimers and tetramers.
  • arylamine compounds having a structure in which three or more triphenylamine structures are linked in the molecule by a single bond or a divalent group containing no heteroatoms such as various triphenylamine trimers and tetramers.
  • PEDOT poly(3,4-ethylenedioxythiophene)
  • PSS poly(styrene sulfonate)
  • P-doped materials such as trisbromophenylamine hexachloroantimony or radialene derivatives (see, for example, Patent Document 3) are used for these layers.
  • a polymer compound having a structure of a benzidine derivative such as TPD in its partial structure can be used.
  • TCTA 4,4′,4′′-tri(N-carbazolyl)triphenylamine
  • TCTA 9,9-bis[4-(carbazole- 9-yl)phenyl]fluorene
  • mCP 1,3-bis(carbazol-9-yl)benzene
  • mCP 2,2-bis(4-carbazol-9-yl-phenyl)adamantane
  • mCP 2,2-bis(4-carbazol-9-yl-phenyl)adamantane
  • triphenylsilyl typified by 9-[4-(carbazol-9-yl)phenyl]-9-[4-(triphenylsilyl)phenyl]-9H-fluorene
  • a compound having an electron blocking action such as a compound having a group and a triarylamine structure can be used.
  • the light emitting layer of the organic EL device of the present invention light emitting metal complexes of quinolinol derivatives such as Alq3 , various metal complexes, anthracene derivatives, bisstyrylbenzene derivatives, pyrene derivatives, oxazole derivatives, polyparaphenylenevinylene derivatives and the like are used. materials can be used.
  • the light-emitting layer may be composed of a host material and a dopant material. As the host material, anthracene derivatives are preferably used.
  • heterocyclic compounds having an indole ring as a condensed ring partial structure heterocyclic compounds having a carbazole ring as a condensed ring partial structure, and carbazole derivatives.
  • thiazole derivatives, benzimidazole derivatives, polydialkylfluorene derivatives and the like can be used.
  • the dopant material quinacridone, coumarin, rubrene, perylene and derivatives thereof, benzopyran derivatives, rhodamine derivatives, aminostyryl derivatives and the like can be used, and green light-emitting materials are particularly preferred.
  • a phosphorescent emitter As the luminescent material, metal complex phosphorescent emitters such as iridium and platinum can be used, green phosphorescent emitters such as Ir(ppy) 3 , blue phosphorescent emitters such as FIrpic, FIr6, Btp2 Red phosphorescent emitters such as Ir(acac) can be used, and green phosphorescent emitters are particularly preferred.
  • phosphorescent emitters metal complex phosphorescent emitters such as iridium and platinum can be used, green phosphorescent emitters such as Ir(ppy) 3 , blue phosphorescent emitters such as FIrpic, FIr6, Btp2 Red phosphorescent emitters such as Ir(acac) can be used, and green phosphorescent emitters are particularly preferred.
  • CBP 4,4′-di(N-carbazolyl)biphenyl
  • TCTA TCTA
  • carbazole derivatives such as mCP
  • UGH2 p-bis(triphenylsilyl)benzene
  • TPBI 1,3,5-phenylene-tris
  • the host material is preferably doped with a phosphorescent light-emitting material in the range of 1 to 30% by weight with respect to the entire light-emitting layer by co-evaporation.
  • Non-Patent Document 4 Materials that emit delayed fluorescence, such as CDCB derivatives such as PIC-TRZ, CC2TA, PXZ-TRZ, and 4CzIPN, as light-emitting materials (see, for example, Non-Patent Document 4).
  • CDCB derivatives such as PIC-TRZ, CC2TA, PXZ-TRZ, and 4CzIPN
  • phenanthroline derivatives such as bathocuproine (hereinafter abbreviated as BCP), aluminum (III) bis(2-methyl-8-quinolinato)-4-phenylphenolate (hereinafter abbreviated as BCP) BAlq) and other metal complexes of quinolinol derivatives, various rare earth complexes, triazole derivatives, triazine derivatives, pyrimidine derivatives, oxadiazole derivatives, benzazole derivatives, and other compounds having a hole-blocking action can be used. These materials may also serve as materials for the electron transport layer.
  • BCP bathocuproine
  • BCP aluminum (III) bis(2-methyl-8-quinolinato)-4-phenylphenolate
  • BAlq other metal complexes of quinolinol derivatives, various rare earth complexes, triazole derivatives, triazine derivatives, pyrimidine derivatives, oxadiazole derivatives, benzazole derivatives, and other compounds having a hole-block
  • Metal complexes of quinolinol derivatives such as Alq 3 and BAlq, various metal complexes, triazole derivatives, triazine derivatives, pyrimidine derivatives, oxadiazole derivatives, pyridine derivatives, and benzimidazole derivatives can be used as the electron transport layer of the organic EL device of the present invention.
  • benzazole derivatives, thiadiazole derivatives, anthracene derivatives, carbodiimide derivatives, quinoxaline derivatives, pyridoindole derivatives, phenanthroline derivatives, silole derivatives and the like can be used.
  • 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 Metal oxides or metals such as ytterbium (Yb), samarium (Sm), calcium (Ca), strontium (Sr), and cesium (Cs) can be used.
  • the electron injection layer can be omitted by preferred selection of the electron transport layer and the cathode.
  • a material that is N-doped with a metal such as cesium can be used in the material normally used for these layers.
  • an electrode material with a low work function such as aluminum, an alloy with a lower work function such as magnesium silver alloy, magnesium calcium alloy, magnesium indium alloy, aluminum magnesium alloy, ITO, IZO or the like is used as an electrode material.
  • An organic thin film containing the compound represented by the general formula (1) is used as the capping layer of the organic EL device of the present invention.
  • the organic thin film used as the capping layer, which contains the compound represented by the general formula (1) has a refractive index of 1.70 or more in the wavelength range of 450 nm to 750 nm from the viewpoint of improving light extraction efficiency. is preferred, and 1.85 or more is particularly preferred.
  • each layer constituting the organic EL element described above may be formed into a film alone, or may be formed by mixing with other materials and used as a single layer, or may be formed alone.
  • a laminated structure of layers formed by mixing layers, layers formed by mixing layers, or layers formed by mixing layers formed by themselves may be used.
  • Thin films of these materials can be formed by known methods such as the spin coating method and the inkjet method in addition to the vapor deposition method.
  • the present invention is not limited to this, and the organic EL element having the bottom emission structure and the organic EL device having the dual emission structure emitting light from both the top and the bottom. The same can be applied to organic EL elements. In these cases, the electrodes in the direction in which light is extracted from the light-emitting element should be transparent or translucent.
  • Example 2 ⁇ Synthesis of exemplary compound (1-3)> 4,4,5,5-tetramethyl instead of 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]dibenzofuran in Example 1 -2-[4-(9-Phenanthrenyl)phenyl]-1,3,2-dioxaborolane was synthesized in the same manner as in Example 1 to give 4.2 g of white powder (yield 57.4%). Obtained.
  • Example 10 ⁇ Synthesis of exemplary compound (1-22)> 4-(2-naphthyl)phenylboronic acid instead of 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]dibenzofuran in Example 9 was synthesized in the same manner as in Example 9 to obtain 3.2 g of white powder (yield 54.9%).
  • Example 11 ⁇ Synthesis of exemplary compound (1-23)> 4,4,5,5-tetramethyl in place of 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]dibenzofuran in Example 9 -2-[4-(9-Phenanthrenyl)phenyl]-1,3,2-dioxaborolane was synthesized in the same manner as in Example 9 to give 8.8 g of white powder (yield 55.0%). Obtained.
  • Example 12 ⁇ Synthesis of exemplary compound (1-24)> Instead of 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]dibenzofuran in Example 9, 2-[4-(4,4, Synthesized in the same manner as in Example 9 using 5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]dibenzothiophene, white powder: 6.7 g (yield 46.0% ).
  • Example 13 ⁇ Synthesis of exemplary compound (1-50)> 4,4,5,5-tetramethyl in place of 3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]dibenzofuran in Example 9 -2-[4-(Phenanthren-2-yl)phenyl]-1,3,2-dioxaborolane was synthesized in the same manner as in Example 9, white powder: 11.0 g (yield 72.8% ).
  • 2,2′-(5-Chloro-1,3-phenylene)bis-naphthalene 10.0 g
  • 4-(2-naphthyl)phenylboronic acid 7.5 g
  • tripotassium phosphate 11.6 g
  • 1,4-dioxane 100 ml and water: 30 ml were added and mixed
  • tricyclohexylphosphine 0.8 g were added and heated under reflux overnight. Stirred. After allowing to cool, water and methanol were added and stirred, and the precipitated solid was collected.
  • Example 15 ⁇ Synthesis of exemplary compound (1-31)> 4,4,5,5-tetramethyl-2-[4-(9-phenanthrenyl)phenyl]-1,3,2-dioxaborolane in place of 4-(2-naphthyl)phenylboronic acid in Example 14 11.4 g of white powder (yield 79.3%) was obtained in the same manner as in Example 14.
  • Example 17 ⁇ Synthesis of exemplary compound (1-35)> 2-[4-(9,9-diphenyl-9H-fluoren-2-yl)phenyl]-4,4,5,5-tetra Synthesis was carried out in the same manner as in Example 14 using methyl-1,3,2-dioxaborolane to obtain 5.9 g of white powder (yield 79.0%).
  • Example 18 ⁇ Synthesis of exemplary compound (1-30)> 2-[4-(dibenzofuran-3-yl)phenyl]-4,4,5,5-tetramethyl-1,3,2-in place of 4-(2-naphthyl)phenylboronic acid in Example 14 Synthesis was carried out in the same manner as in Example 14 using dioxaborolane to obtain 9.5 g of white powder (yield 77.0%).
  • the crude product was purified by crystallization with toluene and acetone, and the precipitated solid was collected to obtain 21.2 g of a white solid of the phenanthrene derivative represented by the following formula (I-1) (yield: 75.0%). rice field.
  • the mixture was dispersed and washed with toluene at 80° C., the insoluble matter was filtered off, and the filtrate was concentrated to obtain a crude product.
  • the crude product was purified by crystallization with toluene and acetone, and the precipitated solid was collected to obtain 22.1 g of a white solid of the phenanthrene derivative represented by the following formula (I-2) (yield: 75.8%). rice field.
  • the product was dispersed and washed with monochlorobenzene at 100° C., the insoluble matter was filtered off, and the filtrate was concentrated to obtain a crude product.
  • the crude product was purified by crystallization with monochlorobenzene and acetone, and the precipitated solid was collected to obtain 8.4 g of white powder (yield 83.7%).
  • Example 23 ⁇ Synthesis of exemplary compound (1-26)> Using 6-chloroquinoline instead of 2-chloroquinoline in Example 22, synthesis was carried out in the same manner as in Example 22 to obtain 6.5 g of white powder (yield 73.6%).
  • Example 24 The melting points and glass transition points of the compounds obtained in the above Examples were measured with a high-sensitivity differential scanning calorimeter (DSC3100SA, manufactured by Bruker AXS). The results are summarized in Table 1.
  • Example 25 Using the compound represented by the general formula (1) obtained in the above example, a deposited film having a thickness of 80 nm was prepared on a silicon substrate, and a spectrometer (F10-RT-UV manufactured by Filmetrics, Inc.) was used. was used to measure the refractive index n and the extinction coefficient k at wavelengths of 450 nm and 750 nm. For comparison, comparative compound (2-1) having the following structural formula and Alq3 were also measured (see, for example, Patent Document 4). Both the compound of the present invention and the comparative example compound have an extinction coefficient k of 0 in the wavelength range of 450 nm to 750 nm, and the measurement results of the refractive index n are summarized in Table 2.
  • the compounds of the present invention have values equal to or higher than those of Alq 3 and the comparative compound (2-1), which indicates that the compounds of the present invention This indicates that an improvement in light extraction efficiency can be expected in an organic EL device in which the capping layer is composed of .
  • Example 26 Organic EL devices manufactured by using the compound of the present invention as a constituent material of the capping layer were measured in air at room temperature, and the measurement results of the luminescence characteristics when a DC voltage was applied are summarized in Table 3.
  • the organic EL device comprises a glass substrate 1 on which a reflective ITO electrode is formed in advance as a metal anode 2, a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, an electron transport layer 5 and an electron transport layer.
  • a layer 6, an electron injection layer 7, a cathode 8, and a capping layer 9 were deposited in this order.
  • a glass substrate 1 on which ITO with a film thickness of 50 nm, a silver alloy reflective film with a film thickness of 100 nm, and an ITO film with a film thickness of 5 nm are formed in this order was subjected to ultrasonic cleaning in isopropyl alcohol for 20 minutes.
  • a compound (3-1) having the following structural formula was formed as a hole transport layer 4 on the hole injection layer 3 so as to have a film thickness of 140 nm.
  • a compound (3-2) of the following structural formula and a compound (3-3) of the following structural formula are deposited as a light-emitting layer 5 at a vapor deposition rate ratio of (3-2):(3- 3)
  • Binary vapor deposition was performed at a vapor deposition rate of 5:95 to form a film having a thickness of 20 nm.
  • a compound (3-4) having the following structural formula and a compound (3-5) having the following structural formula were deposited as an electron transport layer 6 on the light-emitting layer 5 at a deposition rate ratio of (3-4):(3-5).
  • Lithium fluoride was formed as an electron injection layer 7 on the electron transport layer 6 so as to have a thickness of 1 nm.
  • a magnesium-silver alloy was formed as a cathode 8 so as to have a film thickness of 12 nm.
  • the compound (1-1) of Example 1 was formed as a capping layer 9 so as to have a film thickness of 60 nm.
  • Example 27 In Example 26, the same conditions were applied except that the compound (1-3) of Example 2 was formed as the capping layer 9 in place of the compound (1-1) of Example 1 so as to have a thickness of 60 nm. An organic EL device was produced. The characteristics of the produced organic EL device were measured at room temperature in the air, and Table 3 summarizes the measurement results of the luminescence characteristics when a DC voltage was applied.
  • Example 28 In Example 26, the same conditions were applied except that the compound (1-46) of Example 4 was formed as the capping layer 9 in place of the compound (1-1) of Example 1 so as to have a thickness of 60 nm. An organic EL device was produced. The characteristics of the produced organic EL device were measured at room temperature in the air, and Table 3 summarizes the measurement results of the luminescence characteristics when a DC voltage was applied.
  • Example 29 In Example 26, the same conditions were applied except that the compound (1-47) of Example 5 was formed as the capping layer 9 in place of the compound (1-1) of Example 1 so as to have a thickness of 60 nm. An organic EL device was produced. The characteristics of the produced organic EL device were measured at room temperature in the air, and Table 3 summarizes the measurement results of the luminescence characteristics when a DC voltage was applied.
  • Example 30 In Example 26, the same conditions were applied except that the compound (1-48) of Example 6 was formed as the capping layer 9 in place of the compound (1-1) of Example 1 so as to have a thickness of 60 nm. An organic EL device was produced. The characteristics of the produced organic EL device were measured at room temperature in the air, and Table 3 summarizes the measurement results of the luminescence characteristics when a DC voltage was applied.
  • Example 31 In Example 26, the same conditions were applied except that the compound (1-17) of Example 7 was formed as the capping layer 9 in place of the compound (1-1) of Example 1 so as to have a thickness of 60 nm. An organic EL device was produced. The characteristics of the produced organic EL device were measured at room temperature in the air, and Table 3 summarizes the measurement results of the luminescence characteristics when a DC voltage was applied.
  • Example 32 In Example 26, the same conditions were applied except that the compound (1-18) of Example 8 was formed as the capping layer 9 in place of the compound (1-1) of Example 1 so as to have a film thickness of 60 nm. An organic EL device was produced. The characteristics of the produced organic EL device were measured at room temperature in the air, and Table 3 summarizes the measurement results of the luminescence characteristics when a DC voltage was applied.
  • Example 33 In Example 26, the same conditions were applied except that the compound (1-21) of Example 9 was formed as the capping layer 9 in place of the compound (1-1) of Example 1 so as to have a thickness of 60 nm. An organic EL device was produced. The characteristics of the produced organic EL device were measured at room temperature in the air, and Table 3 summarizes the measurement results of the luminescence characteristics when a DC voltage was applied.
  • Example 34 In Example 26, the same conditions were applied except that the compound (1-22) of Example 10 was formed as the capping layer 9 in place of the compound (1-1) of Example 1 so as to have a thickness of 60 nm. An organic EL device was produced. The characteristics of the produced organic EL device were measured at room temperature in the air, and Table 3 summarizes the measurement results of the luminescence characteristics when a DC voltage was applied.
  • Example 35 In Example 26, the same conditions were applied except that the compound (1-23) of Example 11 was formed as the capping layer 9 in place of the compound (1-1) of Example 1 so as to have a film thickness of 60 nm. An organic EL device was produced. The characteristics of the produced organic EL device were measured at room temperature in the air, and Table 3 summarizes the measurement results of the luminescence characteristics when a DC voltage was applied.
  • Example 36 In Example 26, the same conditions were applied except that the compound (1-24) of Example 12 was formed as the capping layer 9 in place of the compound (1-1) of Example 1 so as to have a thickness of 60 nm. An organic EL device was produced. The characteristics of the produced organic EL device were measured at room temperature in the air, and Table 3 summarizes the measurement results of the luminescence characteristics when a DC voltage was applied.
  • Example 37 In Example 26, the same conditions were applied except that the compound (1-33) of Example 14 was formed as the capping layer 9 in place of the compound (1-1) of Example 1 so as to have a thickness of 60 nm. An organic EL device was produced. The characteristics of the produced organic EL device were measured at room temperature in the air, and Table 3 summarizes the measurement results of the luminescence characteristics when a DC voltage was applied.
  • Example 38 In Example 26, the same conditions were applied except that the compound (1-31) of Example 15 was formed to have a film thickness of 60 nm as the capping layer 9 instead of the compound (1-1) of Example 1. An organic EL device was produced. The characteristics of the produced organic EL device were measured at room temperature in the air, and Table 3 summarizes the measurement results of the luminescence characteristics when a DC voltage was applied.
  • Example 39 In Example 26, the same conditions were applied except that the compound (1-34) of Example 16 was formed to have a thickness of 60 nm as the capping layer 9 instead of the compound (1-1) of Example 1. An organic EL device was produced. The characteristics of the produced organic EL device were measured at room temperature in the air, and Table 3 summarizes the measurement results of the luminescence characteristics when a DC voltage was applied.
  • Example 40 In Example 26, the same conditions were applied except that the compound (1-35) of Example 17 was formed as the capping layer 9 in place of the compound (1-1) of Example 1 so as to have a film thickness of 60 nm. An organic EL device was produced. The characteristics of the produced organic EL device were measured at room temperature in the atmosphere, and the measurement results of the luminescence characteristics when a DC voltage was applied are summarized in Table 2.
  • Example 41 In Example 26, the same conditions were applied except that the compound (1-30) of Example 18 was formed as the capping layer 9 in place of the compound (1-1) of Example 1 so as to have a film thickness of 60 nm. An organic EL device was produced. The characteristics of the produced organic EL device were measured at room temperature in the air, and Table 3 summarizes the measurement results of the luminescence characteristics when a DC voltage was applied.
  • Example 42 In Example 26, the same conditions were applied except that the compound (1-36) of Example 19 was formed as the capping layer 9 in place of the compound (1-1) of Example 1 so as to have a thickness of 60 nm. An organic EL device was produced. The characteristics of the produced organic EL device were measured at room temperature in the air, and Table 3 summarizes the measurement results of the luminescence characteristics when a DC voltage was applied.
  • Example 43 In Example 26, the same conditions were applied except that the compound (1-38) of Example 20 was formed as the capping layer 9 in place of the compound (1-1) of Example 1 so as to have a film thickness of 60 nm. An organic EL device was produced. The characteristics of the produced organic EL device were measured at room temperature in the air, and Table 3 summarizes the measurement results of the luminescence characteristics when a DC voltage was applied.
  • Example 44 In Example 26, the same conditions were applied except that the compound (1-39) of Example 21 was formed as the capping layer 9 in place of the compound (1-1) of Example 1 so as to have a thickness of 60 nm. An organic EL device was produced. The characteristics of the produced organic EL device were measured at room temperature in the air, and Table 3 summarizes the measurement results of the luminescence characteristics when a DC voltage was applied.
  • Example 45 In Example 26, the same conditions were applied except that the compound (1-25) of Example 22 was formed as the capping layer 9 in place of the compound (1-1) of Example 1 so as to have a thickness of 60 nm. An organic EL device was produced. The characteristics of the produced organic EL device were measured at room temperature in the air, and Table 3 summarizes the measurement results of the luminescence characteristics when a DC voltage was applied.
  • Example 46 In Example 26, the same conditions were applied except that the compound (1-26) of Example 23 was formed as the capping layer 9 in place of the compound (1-1) of Example 1 so as to have a film thickness of 60 nm. An organic EL device was produced. The characteristics of the produced organic EL device were measured at room temperature in the air, and Table 3 summarizes the measurement results of the luminescence characteristics when a DC voltage was applied.
  • Example 1 For comparison, an organic EL device was fabricated under the same conditions as in Example 26, except that the capping layer 9 was made of Alq3 to a thickness of 60 nm instead of the compound (1-1) of Example 1. was made. The characteristics of the produced organic EL device were measured at room temperature in the air, and Table 3 summarizes the measurement results of the luminescence characteristics when a DC voltage was applied.
  • Example 26 As the capping layer 9, the compound (2-1) was formed to a thickness of 60 nm instead of the compound (1-1) of Example 1 under the same conditions.
  • An organic EL device was produced by The characteristics of the produced organic EL device were measured at room temperature in the air, and Table 3 summarizes the measurement results of the luminescence characteristics when a DC voltage was applied.
  • Table 2 summarizes the results of measuring the device life using the organic EL devices produced in the above examples and comparative examples.
  • the device life was measured as the time required for the device to decay to 95% of the initial luminance of 100% when driven at a constant current of 10 mA/cm 2 .
  • the devices of Comparative Examples 1 and 2 and the devices of Examples 26 to 46 had substantially the same driving voltage at a current density of 10 mA/cm 2 , whereas the luminance and light emission were substantially the same.
  • all the devices of the examples showed remarkable improvement compared to the comparative examples.
  • the compound represented by the general formula (1) of the present invention is a material suitably used for the capping layer, and can increase the refractive index of the capping layer. can be significantly improved.
  • the compound of the present invention has a high refractive index, can significantly improve the light extraction efficiency, and is stable in a thin film state, so it is excellent as a compound suitably used for organic EL devices. Further, an organic EL device produced using the compound of the present invention can obtain high efficiency. Furthermore, the use of the compound of the present invention, which does not absorb light in the respective wavelength regions of blue, green and red, is particularly suitable for displaying clear and bright images with good color purity. For example, it can be expected to be used for home appliances and lighting.

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