WO2009104733A1 - Matière pour dispositif électroluminescent organique et dispositif électroluminescent organique - Google Patents

Matière pour dispositif électroluminescent organique et dispositif électroluminescent organique Download PDF

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WO2009104733A1
WO2009104733A1 PCT/JP2009/053023 JP2009053023W WO2009104733A1 WO 2009104733 A1 WO2009104733 A1 WO 2009104733A1 JP 2009053023 W JP2009053023 W JP 2009053023W WO 2009104733 A1 WO2009104733 A1 WO 2009104733A1
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compound
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substituted
organic
unsubstituted
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泰行 高田
貫 岩田
哲也 金子
純平 早川
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東洋インキ製造株式会社
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Priority claimed from JP2008040803A external-priority patent/JP2009197144A/ja
Priority claimed from JP2008085146A external-priority patent/JP2009235292A/ja
Priority claimed from JP2008225383A external-priority patent/JP2010059293A/ja
Application filed by 東洋インキ製造株式会社 filed Critical 東洋インキ製造株式会社
Publication of WO2009104733A1 publication Critical patent/WO2009104733A1/fr

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Definitions

  • the present invention relates to a material for an organic electroluminescence element used for a flat light source and a display, and an organic electroluminescence element using the same.
  • organic electroluminescence (hereinafter referred to as organic EL) element emits light when electrons injected from a cathode and holes injected from an anode are recombined in an organic phosphor sandwiched between these two electrodes.
  • the organic EL element is expected to be used as a solid light-emitting display element, and has been actively researched and developed in recent years.
  • organic EL elements As for organic EL elements, researches have been made on elements using various materials, and organic EL elements using a hetero five-membered ring compound have been studied. For example, studies on thiophene derivatives (Patent Documents 1 to 4), furan derivatives (Patent Documents 5 to 7), pyrrole derivatives (Patent Documents 8 to 13) and the like have been conducted. Appl. Phys. Lett. 51, 913, 1987 JP-A-4-304466 JP 2000-26451 PR Japanese Laid-Open Patent Publication No. 2005-63679 JP 2003-13054 PR Japanese Laid-Open Patent Publication No. 10-125468 JP 10-152676 A Japanese Laid-Open Patent Publication No. 11-111460 JP 2000-260567 A JP 2003-129044 A Japanese Patent Laid-Open No. 2004-079580 JP 2004-311410 A JP 2004-311412 A JP 2004-335427 A
  • the problem according to one embodiment of the present invention is that, in order to improve the performance of the organic EL, it exhibits higher efficiency than the organic EL element using the materials described in the prior art, has a long life, and has an initial lighting operation. It is to provide a material for an organic EL element and an organic EL element in which the decrease in luminance is moderate. Improving the efficiency of the organic EL element can obtain a strong luminance even with a small electric energy, is very important for lowering the driving voltage of the element, and can also suppress the electric load applied to the element. , Leading to longer life of the element. That is, the subject by one embodiment of this invention is providing the organic EL element which shows the outstanding characteristics, such as a low voltage drive, long life, and heat resistance.
  • one embodiment of the present invention relates to a material for an organic electroluminescence device, which is a compound represented by the following general formula [1].
  • Ar 1 and Ar 2 are each independently a substituted or unsubstituted divalent aromatic hydrocarbon group or a substituted or unsubstituted divalent aromatic heterocyclic group
  • Ar 3 is a substituted or unsubstituted condensed aromatic hydrocarbon group, or a substituted or unsubstituted condensed aromatic heterocyclic group
  • Ar 4 is a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group
  • X is S, O, or N—Ar 5 , wherein Ar 5 is a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group, R 1 and R 2 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted
  • R 1 and R 2 may combine to form a ring.
  • at least one layer contains the material for an organic electroluminescence element in an organic electroluminescence element in which a single layer or a multilayer organic layer is formed between a pair of electrodes including an anode and a cathode.
  • the present invention relates to an organic electroluminescence element which is a layer.
  • the light emitting layer is a layer containing the material for an organic electroluminescent element. It is related with the organic electroluminescent element which is.
  • the organic electroluminescence device material is used as a light emitting layer host material.
  • the present invention relates to an organic electroluminescence device.
  • the electron transport layer contains the material for an organic electroluminescence device.
  • the present invention relates to an organic electroluminescence element which is a layer.
  • the organic EL device using the compound represented by the general formula [1] realizes high luminance, high efficiency, long life, and high initial stability.
  • Ar 1 and Ar 2 in the general formula [1] represent a substituted or unsubstituted divalent aromatic hydrocarbon group or a substituted or unsubstituted divalent aromatic heterocyclic group.
  • examples of the divalent aromatic hydrocarbon group include a phenylene group, a naphthylene group, an anthrylene group, a phenanthrenylene group, a fluorenylene group, a tetrasenylene group, a pentasenylene group, and a peryleneylene group.
  • a phenylene group, a naphthylene group, an anthrylene group, and a phenanthrenylene group are preferable.
  • examples of the divalent aromatic heterocyclic group include a pyridylene group, a quinolinylene group, an isoquinolinylene group, a phenanthrolinylene group, a benzothienylene group, a benzofurylene group, and an indolylene group.
  • a pyridylene group, a quinolinylene group, and a benzofurylene group are preferable.
  • Ar 3 represents a substituted or unsubstituted condensed aromatic hydrocarbon group or a substituted or unsubstituted condensed aromatic heterocyclic group.
  • examples of the condensed aromatic hydrocarbon group include a naphthyl group, an anthryl group, a phenanthryl group, a pentacenyl group, a tetraphenylenyl group, a pyrenyl group, a perylenyl group, and a fluorenyl group.
  • a naphthyl group, an anthryl group, a phenanthryl group, and a fluorenyl group are preferable.
  • examples of the condensed aromatic heterocyclic group include a quinolinyl group, an isoquinolinyl group, a benzothiophenyl group, a benzofuryl group, an indolyl group, a phenanthrolinyl group, and a carbazolyl group.
  • a quinolinyl group, a benzothiophenyl group, a benzofuryl group, and a carbazolyl group are preferable.
  • Ar 4 represents a hydrogen atom, a substituted or unsubstituted aromatic hydrocarbon group, or a substituted or unsubstituted aromatic heterocyclic group.
  • examples of the aromatic hydrocarbon group include a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a pentacenyl group, a tetraphenylenyl group, a pyrenyl group, a perylenyl group, and a fluorenyl group. It is done. Of these, phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, and fluorenyl are preferred.
  • aromatic heterocyclic group examples include pyridyl group, pyrazinyl group, pyrimidinyl group, triazinyl group, quinolinyl group, isoquinolinyl group, benzothiophenyl group, benzofuryl group, indolyl group, phenanthrolinyl group, carbazolyl group and the like. It is done. Among these, a pyridyl group, a pyrazinyl group, a quinolinyl group, a benzothiophenyl group, a benzofuryl group, and a carbazolyl group are preferable.
  • X is S, O, N—Ar 5 .
  • Ar 5 represents a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted aromatic heterocyclic group.
  • examples of the aromatic hydrocarbon group and aromatic heterocyclic group in Ar 5 include the same aromatic hydrocarbon group and aromatic heterocyclic group as Ar 4 .
  • Ar 1 to Ar 5 may have a substituent.
  • substituents that Ar 1 to Ar 5 may have include an alkyl group, an aromatic hydrocarbon group, an aromatic heterocyclic group, an alkoxy group, and an aryloxy group.
  • examples of the alkyl group include an alkyl group having 1 to 18 carbon atoms.
  • alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, and the like.
  • An alkyl group having 1 to 4 carbon atoms is preferable, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, and a t-butyl group.
  • the aromatic hydrocarbon group include the same as the aromatic hydrocarbon group in Ar 4.
  • the aromatic heterocyclic group include the same as the aromatic heterocyclic group in Ar 4.
  • examples of the alkoxy group include alkoxy groups such as a methoxy group, an ethoxy group, a butoxy group, an octyloxy group, and a decyloxy group. Among these, a methoxy group, an ethoxy group, and a butoxy group are preferable.
  • aryloxy group is a group in which —O— is bonded to the same group as the aromatic hydrocarbon group in Ar 4 , and examples thereof include a phenoxy group and a naphthyloxy group.
  • R 1 and R 2 in the general formula [1] are a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted Alternatively, it represents an unsubstituted alkoxy group or a substituted or unsubstituted aryloxy group.
  • R 1 and R 2 may combine to form a ring.
  • alkyl group aromatic hydrocarbon group, aromatic heterocyclic group, alkoxy group, and aryloxy group in R 1 and R 2
  • an alkyl group in Ar 1 to Ar 5 an aromatic hydrocarbon group
  • an aromatic heterocyclic group, an alkoxy group, and an aryloxy group is mentioned.
  • R 1 and R 2 may have a substituent.
  • examples of the substituent that R 1 and R 2 may have include the same substituents that Ar 1 to Ar 5 may have.
  • Table 1 below shows typical examples of organic EL device materials represented by the general formula [1] that can be used in the organic EL device of the present invention (Exemplary Compounds 1 to 440). It is not limited to.
  • the compound group represented by the general formula [1] can be obtained by a known method. For example, a reaction of 2 to 3 stages is performed using 4-bromophenacyl bromide and 4′-bromoacetophenone as starting materials. (For example, Synthesis, 2000, 1259, Organic Synthesis, Coll. Vol. 10, 418, Synthesis, 1982, 1061, The Journal of Organic Chemistry, 2007, Vol. 72, 69, Vol. 72, 69, Vol. (Organic Chemistry, 2003, Vol. 68, 5392-5394, Journal of Medicinal Chemistry, Vol 44, 3838, etc.). Although the example of a reaction is given to the following, this invention is not limited to these.
  • the organic EL element is composed of an element in which a single layer or a multilayer organic layer is formed between an anode and a cathode.
  • the single layer type organic EL element is an element composed of only a light emitting layer between an anode and a cathode.
  • the multilayer organic EL element facilitates injection of holes and electrons into the light emitting layer in addition to the light emitting layer, and facilitates recombination of holes and electrons in the light emitting layer. In order to do so, it refers to a layer in which a hole injection layer, a hole transport layer, a hole blocking layer, an electron injection layer, an electron transport layer, and the like are laminated.
  • typical element configurations of the multilayer organic EL element include (1) anode / hole injection layer / light emitting layer / cathode, and (2) anode / hole injection layer / hole transport layer / light emitting layer / cathode.
  • Anode / hole injection layer / light emitting layer / electron injection layer / cathode (3) Anode / hole injection layer / light emitting layer / electron injection layer / cathode, (4) Anode / hole injection layer / hole transport layer / light emitting layer / electron injection layer / cathode, (5) Anode / positive Hole injection layer / light emitting layer / hole blocking layer / electron injection layer / cathode, (6) anode / hole injection layer / hole transport layer / light emitting layer / hole blocking layer / electron injection layer / cathode, (7) Anode / light emitting layer / hole blocking layer / electron injection layer / cathode, (8) anode / light emitting layer / electron injection layer / cathode, (9) anode / hole injection layer / hole transport layer / light emitting layer / electron transport (10) An element structure in which a multilayer structure such as an anode /
  • each of the organic layers described above may be formed of two or more layers, and several layers may be repeatedly laminated.
  • an element configuration called “multi-photon emission” in which a part of the multilayer organic EL element is multilayered has been proposed in recent years for the purpose of improving light extraction efficiency.
  • the charge generating layer and the light emitting unit A method of laminating a plurality of layers is an example.
  • the organic EL device material of the present invention may be used in any of the above-mentioned layers, but can be suitably used particularly for a light emitting layer or an electron transport layer.
  • the light emitting layer may be formed from a single material or may be formed from a plurality of materials.
  • a material used for the light emitting layer in addition to the organic EL device material of the present invention, further known light emitting materials, doping materials, hole injecting materials, and electron injecting materials can be used.
  • various luminance colors such as red, blue, and green can be obtained.
  • white light emission can be obtained by combining a plurality of light emitting materials.
  • Examples of the light emitting material or doping material that can be used for the light emitting layer together with the organic EL device material of the present invention include anthracene derivatives, naphthalene derivatives, phenanthrene derivatives, pyrene derivatives, tetracene derivatives, coronene derivatives, chrysene derivatives, fluorescein derivatives, perylene derivatives, phthaloperylene.
  • naphthaloperylene derivatives perinone derivatives, phthaloperinone derivatives, naphthaloperinone derivatives, diphenylbutadiene derivatives, tetraphenylbutadiene derivatives, coumarin derivatives, oxadiazole derivatives, aldazine derivatives, bisbenzoxazoline derivatives, bisstyryl derivatives, diketopyrrolopyrrole derivatives, pyromethenes
  • Derivatives pyrazine derivatives, cyclopentadiene derivatives, quinoline metal complex derivatives, diphenylethylene derivatives, Luanthracene derivatives, carbazole derivatives, pyran derivatives, thiopyran derivatives, polymethine derivatives, merocyanine derivatives, imidazole chelating oxinoid compounds, quinacridone derivatives, rubrene derivatives, fluorescent dyes for dye lasers and whitening, etc. Is not to be done.
  • the light emitting layer constituting material that can be suitably used includes naphthalene derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, tetracene derivatives, perylene derivatives, carbazole derivatives, diketopyrrolopyrrole derivatives, pyromethene derivatives, quinoline series Metal complex.
  • a phosphorescent light emitting material can also be used.
  • the compound of the present invention can be used as a host material in the light emitting layer.
  • the phosphorescent light-emitting material here means a compound that emits light when transitioning from an excited triplet state to a ground state. Examples of the phosphorescent material that can be used in the organic electroluminescence device of the present invention include an organometallic complex.
  • the metal atom in the organometallic complex is usually a transition metal, preferably 5th or 6th period in the period, 6 to 11 group in the group, more preferably 8 to 10 group elements. Specific examples include iridium and platinum. Further, examples of the ligand include 2-phenylpyridine and 2- (2'-benzothienyl) pyridine, and the carbon atom on these ligands is directly bonded to the metal. Another example is a porphyrin or tetraazaporphyrin ring complex, and the central metal includes platinum.
  • a polymer can be used for the light emitting layer in order to function as a hole transport layer or an electron transport layer, or to improve film formability.
  • an antioxidant, an ultraviolet absorber, and a plasticizer can be used to improve film formability and prevent pinholes in the film.
  • the polymer include insulating resins such as polystyrene, polycarbonate, polyacrylate, polyester, polyamide, polyurethane, polysulfone, polymethyl methacrylate, polymethyl acrylate, and cellulose, and copolymers thereof, poly-N-vinylcarbazole. And photoconductive resins such as polysilane, and conductive resins such as polythiophene and polypyrrole.
  • the mixing ratio of each material is not particularly limited.
  • the abundance ratio in a light emitting layer in the case of using the organic EL element material of this invention for a light emitting layer is not specifically limited. That is, the organic EL device material of the present invention may be used alone or as a host or a dopant in the light emitting layer.
  • a hole injection material that exhibits an excellent hole injection effect with respect to the light emitting layer and that can form a hole injection layer excellent in adhesion to the anode interface and thin film formation is used.
  • the materials used for the materials may be referred to as a hole-injecting material and a hole-transporting material, respectively.
  • hole injection materials or hole transport materials include, in addition to the compounds of the present invention, phthalocyanine derivatives, naphthalocyanine derivatives, porphyrin derivatives, oxadiazole derivatives, triazole derivatives, imidazole derivatives, imidazolone derivatives, imidazoles.
  • Low molecular weight compounds such as thione derivatives, pyrazoline derivatives, pyrazolone derivatives, tetrahydroimidazole derivatives, oxazole derivatives, oxadiazole derivatives, hydrazone derivatives, acylhydrazone derivatives, stilbene derivatives, aromatic tertiary amine derivatives, polyvinylcarbazole derivatives, polysilane derivatives
  • the polymer compound include, but are not limited to, materials that can form a thin film necessary for device fabrication, inject holes from the anode, and transport holes. Not.
  • examples of the hole injection material or the hole transport material that can be particularly preferably used include aromatic tertiary amine derivatives and phthalocyanine derivatives.
  • aromatic tertiary amine derivatives include N, N′-diphenyl-N, N ′-(3-methylphenyl) -1,1′-biphenyl-4,4′-diamine, N, N, N ′.
  • N ′-(4-methylphenyl) -1,1′-phenyl-4,4′-diamine N, N, N ′, N ′-(4-methylphenyl) -1,1′-biphenyl-4 , 4′-diamine, N, N′-diphenyl-N, N′-dinaphthyl-1,1′-biphenyl-4,4′-diamine, N, N ′-(methylphenyl) -N, N ′-( 4-n-butylphenyl) -phenanthrene-9,10-diamine, N, N-bis (4-di-4-tolylaminophenyl) -4-phenyl-cyclohexane, and oligomers having these aromatic tertiary amine skeletons Or a polymer, which is a hole injection material or a hole transport material.
  • phthalocyanine (Pc) derivative examples include H 2 Pc, CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl 2 SiPc, (HO) AlPc, (HO)
  • phthalocyanine derivatives such as GaPc, VOPc, TiOPc, MoOPc, and GaPc—O—GaPc, and these can be suitably used particularly for hole injection materials.
  • the electron injection layer and the electron transport layer have an electron injection effect and an electron transport effect which are excellent with respect to the light emitting layer, respectively, and can form an electron injection layer with excellent adhesion to the cathode interface and excellent thin film formation.
  • Material is used.
  • electron injection materials include, in addition to the compounds of the present invention, metal complex compounds, nitrogen-containing five-membered ring derivatives, fluorenone derivatives, anthraquinodimethane derivatives, diphenoquinone derivatives, thiopyran dioxide oxide derivatives, perylene tetra
  • Examples thereof include carboxylic acid derivatives, fluorenylidenemethane derivatives, anthrone derivatives, silole derivatives, calcium acetylacetonate, sodium acetate and the like.
  • electron injection materials include inorganic / organic composite materials doped with metal such as cesium in bathophenanthroline, BCP, TPP, T5MPyTZ, etc. (Proceedings of the Society of Polymer Science, Vol. 50, No. 4, page 660). , 2001, Proceedings of the 50th Joint Physics Conference on Applied Physics, No. 3, page 1402, 2003), forming a thin film necessary for device fabrication, and injecting electrons from the cathode.
  • the material is not particularly limited as long as it can be transported.
  • particularly effective materials include the compounds of the present invention, metal complex compounds, and nitrogen-containing five-membered ring derivatives.
  • preferable metal complex compounds include tris (8-quinolinolato) aluminum, tris (2-methyl-8-quinolinolato) aluminum, and tris (5-phenyl-8-quinolinolato) aluminum.
  • preferred nitrogen-containing five-membered ring derivatives include oxazole derivatives, thiazole derivatives, oxadiazole derivatives, thiadiazole derivatives, and triazole derivatives.
  • hole blocking material that can prevent a hole from passing through the light emitting layer from reaching the electron injection layer and form a layer having excellent thin film formability is used for the hole blocking layer.
  • hole blocking materials include aluminum complex compounds such as bis (8-quinolinolato) (4-phenylphenolate) aluminum, and bis (2-methyl-8-quinolinolato) (4-phenylphenolate).
  • aluminum complex compounds such as bis (8-quinolinolato) (4-phenylphenolate) aluminum, and bis (2-methyl-8-quinolinolato) (4-phenylphenolate).
  • gallium complex compounds such as gallium and nitrogen-containing condensed aromatic compounds such as 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP).
  • the materials used for the anode of the organic EL device of the present invention are metals such as carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum, palladium, and alloys thereof, zinc oxide, oxidation Examples thereof include conductive metal oxides such as tin, indium oxide and indium tin oxide (ITO), and conductive polymers such as polythiophene, polypyrrole and polyaniline.
  • a conductive material used for the anode of the organic EL device of the present invention a material having a resistance value as low as possible is preferable, and ITO glass and NESA glass are preferably used.
  • the material used for the cathode of the organic EL device of the present invention is not particularly limited as long as it can efficiently inject electrons into the organic EL device, but in general, platinum, gold, silver, copper, iron, tin, Examples thereof include zinc, aluminum, indium, chromium, lithium, sodium, potassium, calcium, magnesium, and alloys thereof.
  • examples of the alloy include magnesium / silver, magnesium / indium, lithium / aluminum, and the like, but alloys containing a low work function metal such as lithium, sodium, potassium, calcium, and magnesium are preferable.
  • an inorganic salt such as lithium fluoride can be used in place of the low work function metal.
  • cathodes can be produced by methods known in the industry such as resistance heating, electron beam irradiation, sputtering, ion plating, and coating.
  • the anode and cathode described above may be formed with a layer structure of two or more layers as necessary.
  • the substrate material on the surface from which light is extracted is sufficiently transparent.
  • the transmittance in the light emission wavelength region of light emitted from the device is 50% or more, preferably 90% or more.
  • These substrates have mechanical and thermal strength and are not particularly limited as long as they are transparent.
  • transparent polymers such as polyethylene, polyethersulfone, polypropylene, and PET are recommended.
  • each layer of the organic EL device of the present invention a dry film forming method such as vacuum deposition, electron beam irradiation, sputtering, plasma, ion plating, or a wet process such as spin coating, dipping, or flow coating is used. Any of the membrane methods can be applied.
  • the film thickness of each layer is not particularly limited, but if the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. Conversely, if the film thickness is too thin, pinholes, etc. And it becomes difficult to obtain sufficient light emission luminance even when an electric field is applied. Accordingly, the thickness of each layer is suitably in the range of 1 nm to 1 ⁇ m, but more preferably in the range of 10 nm to 0.2 ⁇ m.
  • a protective layer may be provided on the surface of the element, or the entire element may be covered or sealed with a resin or the like.
  • a photocurable resin that is cured by light is preferably used.
  • this organic EL element can obtain light emission exhibiting high color purity and luminance at a low driving voltage. Therefore, this organic EL device can be applied to flat panel displays such as wall-mounted televisions and flat light emitters, as well as light sources such as copiers and printers, light sources such as liquid crystal displays and instruments, display boards, and indicator lights. Can be considered.
  • Synthesis Example 30 Synthesis of Exemplary Compound 1 Intermediate 300 (3.50 g) 1-naphthaleneboronic acid (2.44 g), tetrakis (triphenylphosphine) palladium (0) (0.51 g), toluene (100 mL), 2M aqueous potassium carbonate solution (100 mL) was added, and the mixture was stirred at 80 ° C. for 5 hours under a nitrogen atmosphere. After cooling the reaction solution, the organic layer was separated, and the aqueous layer was extracted with toluene (3 ⁇ 50 mL). This was combined with the previous organic layer and dried over magnesium sulfate.
  • Synthesis Example 45 Synthesis of Exemplary Compound 131 Intermediate 15 (2.50 g), 1-naphthaleneboronic acid (3.41 g), tetrakis (triphenylphosphine) palladium (0) (0.38 g), toluene (100 mL) in a 300 mL flask 2M aqueous potassium carbonate solution (100 mL) was added, and the mixture was stirred at 80 ° C. for 2.5 hours under a nitrogen atmosphere. After cooling the reaction solution, the organic layer was separated, and the aqueous layer was extracted with toluene (3 ⁇ 50 mL). This was combined with the previous organic layer and dried over magnesium sulfate.
  • Synthesis Example 61 Synthesis of Exemplary Compound 172
  • the same reaction was performed using benzo [b] thiophen-2-ylboronic acid (1.96 g) instead of 2-naphthaleneboronic acid.
  • Compound 172 (3.27 g) was obtained.
  • EI-MS m / z 478 Molecular weight: 478).
  • Example 1 ⁇ -NPD (the following compound A) was vacuum-deposited on the cleaned glass plate with an ITO electrode to obtain a hole injection layer having a thickness of 75 nm. Subsequently, the exemplary compound 1 of this invention was vacuum-deposited and the light emitting layer with a film thickness of 40 nm was obtained. Further, TPBI (compound B below) is vacuum-deposited to form an electron injection layer having a thickness of 20 nm, on which first 1 nm of lithium fluoride and then 150 nm of aluminum (Al) are evaporated to form an electrode, An organic EL device was obtained.
  • TPBI compound B below
  • Examples 2 to 11 A device was prepared in the same manner as in Example 1 except that a light emitting layer was prepared using the compounds shown in Table 2 below instead of Compound 1. The efficiency was measured when this device was driven at a constant current at room temperature with an emission luminance of 300 (cd / m 2 ). In addition, initial luminance when driven at a current density of 12.5 mA / cm 2 and luminance after continuous driving for 100 hours in an environment of 30 ° C. were measured. The results are shown in Table 2.
  • Comparative Example 1 A device was prepared in the same manner as in Example 1 except that a light emitting layer was prepared using the following compound C instead of the compound 1. The efficiency was measured when this device was driven at a constant current at room temperature with an emission luminance of 300 (cd / m 2 ). In addition, initial luminance when driven at a current density of 12.5 mA / cm 2 and luminance after continuous driving for 100 hours in an environment of 30 ° C. were measured. The results are shown in Table 2.
  • Example 12 The following compound D was vacuum-deposited on a glass plate with an ITO electrode to obtain a hole injection layer having a thickness of 70 nm. Next, Compound 1 and the following Compound E were co-evaporated at a composition ratio of 5: 100 to form a light emitting layer having a thickness of 40 nm. Further, TPBI was deposited to form an electron injection layer having a thickness of 20 nm. On top of that, a cathode was formed by vapor deposition of 1 nm of lithium fluoride and 100 nm of Al to obtain an organic EL device.
  • Examples 13-31 A device was prepared in the same manner as in Example 12 except that the compounds in Table 3 were used instead of Compound 1.
  • the emission color was blue and the emission efficiency was 4 cd / A or more.
  • initial luminance when driven at a current density of 12.5 mA / cm 2 and luminance after continuous driving for 100 hours in an environment of 30 ° C. were measured. The results are shown in Table 3.
  • Comparative Examples 2-3 A device was prepared in the same manner as in Example 12 except that Compound C (Comparative Example 2) and the following Compound F (Comparative Example 3) were used instead of Compound 1. Luminous efficiency was measured when these devices were driven at a constant current at room temperature with an emission luminance of 300 (cd / m 2 ). In addition, initial luminance when driven at a current density of 12.5 mA / cm 2 and luminance after continuous driving for 100 hours in an environment of 30 ° C. were measured. The results are shown in Table 3.
  • Example 32 The following compound G was vacuum-deposited on a glass plate with an ITO electrode to obtain a hole injection layer having a thickness of 80 nm. Next, Compound E and Compound 1 were co-evaporated at a weight composition ratio of 100: 3 to form a light emitting layer having a thickness of 30 nm. Further, Compound B was deposited to form an electron injection layer having a thickness of 30 nm. A cathode was formed thereon by vapor deposition of 1 nm of lithium oxide (Li 2 O) and 100 nm of Al to obtain an organic EL device. When this element was driven at a constant current at room temperature with an emission luminance of 300 (cd / m 2 ), the light emission efficiency was 5.2 cd / A. In addition, initial luminance when driven at a current density of 12.5 mA / cm 2 and luminance after continuous driving for 100 hours in an environment of 30 ° C. were measured. The results are shown in Table 4.
  • Examples 33 to 50 A device was prepared in the same manner as in Example 32 except that the compounds in Table 4 were used instead of Compound 1.
  • the luminous efficiency is 4 cd / A or more, and when the elements are driven at a current density of 12.5 mA / cm 2.
  • the initial brightness and the brightness after 100 hours of continuous driving in an environment of 30 ° C. were measured. The results are shown in Table 4.
  • Comparative Example 4 A device was prepared in the same manner as in Example 32 except that Compound C was used instead of Compound 1. Luminous efficiency was measured when this device was driven at a constant current at room temperature with an emission luminance of 300 (cd / m 2 ). In addition, initial luminance when driven at a current density of 12.5 mA / cm 2 and luminance after continuous driving for 100 hours in an environment of 30 ° C. were measured. The results are shown in Table 4.
  • Example 51 Compound D was vacuum deposited on a glass plate with an ITO electrode to obtain a 65 nm-thick hole injection layer. Next, the following compound H and compound 1 were co-evaporated at a composition ratio of 3: 100 to form a light emitting layer having a thickness of 30 nm. Further, TPBI was deposited to form an electron injection layer having a thickness of 30 nm. On top of that, a cathode was formed by vapor deposition of 1 nm of lithium fluoride and 100 nm of Al to obtain an organic EL device.
  • Examples 52-74 A device was prepared in the same manner as in Example 51 except that the compound in Table 5 was used instead of Compound 1.
  • the luminous efficiency was 5 cd / A or more.
  • the initial luminance when driven at a current density of 12.5 mA / cm 2 , and continuous driving for 100 hours in an environment of 30 ° C., followed by continuous driving for 24 hours in an environment of 100 ° C., after each driving The brightness of was measured. The results are shown in Table 5.
  • Comparative Example 5 A device was prepared in the same manner as in Example 51 except that the following compound I was used instead of compound 1. Luminous efficiency was measured when this device was driven at a constant current at room temperature with an emission luminance of 300 (cd / m 2 ). In addition, the initial luminance when driven at a current density of 12.5 mA / cm 2 , and continuous driving for 100 hours in an environment of 30 ° C., followed by continuous driving for 24 hours in an environment of 100 ° C., after each driving The brightness of was measured. The results are shown in Table 5.
  • Example 75 Compound G was vacuum-deposited on a glass plate with an ITO electrode to obtain a hole injection layer having a thickness of 60 nm. Next, the following compound J and compound 1 were co-evaporated at a composition ratio of 2: 100 to form a light emitting layer having a thickness of 40 nm. Further, TPBI was deposited to form an electron injection layer having a thickness of 40 nm. On top of that, a cathode was formed by vapor deposition of 1 nm of lithium fluoride and 100 nm of Al to obtain an organic EL device.
  • Examples 76-83 A device was prepared in the same manner as in Example 75 except that the compounds in Table 6 were used instead of Compound 1.
  • the light emission efficiency is 4 cd / A or more, and when the elements are driven at a current density of 12.5 mA / cm 2 .
  • the initial luminance and the luminance after being continuously driven for 100 hours in an environment of 30 ° C. were measured. The results are shown in Table 6.
  • Example 84 The following compound K was vapor-deposited on a glass plate with an ITO electrode to form a hole injection layer having a film thickness of 60 nm. Next, the compound 2 of Table 1 and the following compound L were co-evaporated with the composition ratio of 100: 5, and the light emitting layer with a film thickness of 40 nm was formed. Further, Balq (compound M below) is vapor-deposited to form a 10 nm-thick hole blocking layer, and then Alq3 (tris (8-hydroxyquinoline) aluminum) is vacuum-deposited thereon to form a 30-nm thick electron.
  • Balq compound M below
  • Alq3 tris (8-hydroxyquinoline) aluminum
  • An injection layer was formed, and an electrode was formed thereon by first depositing 1 nm of lithium fluoride and then 200 nm of Al, thereby obtaining an organic EL device.
  • this device was driven at a constant current at room temperature with an emission luminance of 300 (cd / m 2 ), it emitted blue light and its luminous efficiency was 9.5 cd / A.
  • Examples 85-87 A device was prepared in the same manner as in Example 84 except that the compounds in Table 7 were used instead of Compound 2. When these devices were driven at a constant current at room temperature with an emission luminance of 300 (cd / m 2 ), the luminous efficiency was 9 cd / A or more. The results are shown in Table 7.
  • Example 88 PEDOT / PSS (poly (3,4-ethylenedioxy) -2,5-thiophene / polystyrene sulfonic acid, BAYTRON P VP CH8000 manufactured by Bayer) manufactured on a cleaned glass plate with an ITO electrode by spin coating A hole injection layer having a thickness of 50 nm was obtained. Next, 60% of PVK (polyvinylcarbazole), 4% of compound 77, and 36% of electron transport material (compound N below) were dissolved in toluene at a concentration of 2.0 wt%, and the film thickness of 60 nm was obtained by spin coating. A light emitting layer was obtained.
  • PVK polyvinylcarbazole
  • compound N electron transport material
  • Example 89 PEDOT / PSS (poly (3,4-ethylenedioxy) -2,5-thiophene / polystyrene sulfonic acid, BAYTRON P VP CH8000 manufactured by Bayer) manufactured on a cleaned glass plate with an ITO electrode by spin coating A hole injection layer having a thickness of 50 nm was obtained. Next, 60% PVK (polyvinylcarbazole), 5% compound 82 and 35% electron transport material (compound O below) were dissolved in toluene at a concentration of 2.0 wt%, and the film thickness was 70 nm by spin coating. A light emitting layer was obtained.
  • Example 90 On the washed glass plate with an ITO electrode, the compound 32 of the present invention was vacuum-deposited to obtain a hole injection layer having a thickness of 50 nm. Compound A was then vacuum deposited to obtain a 30 nm hole transport layer. Further, Alq3 is vacuum-deposited to form an electron-injection type light-emitting layer having a film thickness of 50 nm, and then an electrode is formed by first depositing 1 nm of lithium fluoride and then 200 nm of Al to form an electrode. It was. When this device was subjected to an energization test, yellow light emission with a maximum light emission luminance of 1610 cd / m 2 was obtained.
  • Example 91 Compound D was deposited on a glass plate with an ITO electrode to form a 50 nm-thick hole injection layer, and then compound 50 was deposited to form a 30 nm-thick hole transport layer. Next, Alq3 was deposited to form an electron injecting light emitting layer having a thickness of 50 nm, and an electrode was formed thereon by vacuum deposition of 1 nm of lithium fluoride and 200 nm of Al, thereby obtaining an organic EL device. When an energization test was performed on this device, yellow light emission with a maximum light emission luminance of 1840 cd / m 2 was obtained.
  • Example 92 Compound D was vacuum-deposited on a glass plate with an ITO electrode to obtain a hole injection layer having a thickness of 50 nm. Next, Alq3 was deposited to form a light-emitting layer having a thickness of 40 nm. Further, Compound 19 was deposited to form an electron injection layer having a thickness of 30 nm. On top of that, a cathode was formed by vapor deposition of 1 nm of lithium fluoride and 100 nm of Al to obtain an organic EL device. When this device was subjected to an energization test, yellow light emission with a maximum light emission luminance of 1740 cd / m 2 was obtained.
  • Example 93 A device was prepared in the same manner as in Example 92 except that Compound 15 was used instead of Compound 19. When this device was subjected to an energization test, yellow light emission with a maximum light emission luminance of 1580 cd / m 2 was obtained.
  • Example 94 ⁇ -NPD was vacuum-deposited on the cleaned glass plate with an ITO electrode to obtain a hole injection layer having a thickness of 60 nm. Subsequently, the compound 131 was vacuum-deposited and the light emitting layer with a film thickness of 30 nm was obtained. Further, TPBI was vacuum-deposited to form an electron injection layer having a film thickness of 30 nm, and an electrode was formed thereon by first depositing 1 nm of lithium fluoride and then 150 nm of Al, thereby obtaining an organic EL device.
  • Examples 95-108 A device was prepared in the same manner as in Example 94 except that a light emitting layer was prepared using the compounds shown in Table 8 below instead of the compound 131. The efficiency was measured when this device was driven at a constant current at room temperature with an emission luminance of 300 (cd / m 2 ). In addition, initial luminance when driven at a current density of 12.5 mA / cm 2 and luminance after continuous driving for 100 hours in an environment of 30 ° C. were measured. The results are shown in Table 8.
  • Comparative Example 6 A device was prepared in the same manner as in Example 94 except that a light emitting layer was prepared using the following compound P instead of the compound 131. The efficiency was measured when this device was driven at a constant current at room temperature with an emission luminance of 300 (cd / m 2 ). In addition, initial luminance when driven at a current density of 12.5 mA / cm 2 and luminance after continuous driving for 100 hours in an environment of 30 ° C. were measured. The results are shown in Table 8.
  • Example 109 The following compound Q was vacuum-deposited on a glass plate with an ITO electrode to obtain a hole injection layer having a thickness of 80 nm. Next, the compound 131 and the following compound R were co-evaporated at a composition ratio of 3: 100 to form a light emitting layer having a thickness of 35 nm. Further, TPBI was deposited to form an electron injection layer having a thickness of 35 nm. On top of that, a cathode was formed by vapor deposition of 1 nm of lithium fluoride and 100 nm of Al to obtain an organic EL device.
  • Examples 110-130 A device was prepared in the same manner as in Example 109 except that the compound shown in Table 9 was used instead of the exemplified compound 131.
  • the emission color was blue, and the emission efficiency was 5 cd / A or more.
  • initial luminance when driven at a current density of 12.5 mA / cm 2 and luminance after continuous driving for 100 hours in an environment of 30 ° C. were measured. The results are shown in Table 9.
  • Comparative Examples 7-8 A device was prepared in the same manner as in Example 109 except that Compound P (Comparative Example 7) and the following Compound S (Comparative Example 8) were used instead of Compound 131. Luminous efficiency was measured when these devices were driven at a constant current at room temperature with an emission luminance of 300 (cd / m 2 ). In addition, initial luminance when driven at a current density of 12.5 mA / cm 2 and luminance after continuous driving for 100 hours in an environment of 30 ° C. were measured. The results are shown in Table 9.
  • Example 131 The following compound T was vacuum-deposited on a glass plate with an ITO electrode to obtain a hole injection layer having a thickness of 60 nm. Next, Compound R and Exemplary Compound 133 were co-evaporated at a weight composition ratio of 100: 3 to form a light emitting layer with a thickness of 30 nm. Further, Compound B was deposited to form an electron injection layer having a thickness of 30 nm. A cathode was formed thereon by vapor deposition of 1 nm of Li 2 O and 100 nm of Al to obtain an organic EL device.
  • Examples 132-141 A device was prepared in the same manner as in Example 131 except that the compound in Table 10 was used instead of the compound 133.
  • the emission color is blue
  • the emission efficiency is 5 cd / A or more
  • the current density is 12.
  • the initial luminance when driven at 5 mA / cm 2 and the luminance after continuous driving for 100 hours in an environment of 30 ° C. were measured. The results are shown in Table 10.
  • Comparative Example 9 A device was prepared in the same manner as in Example 131 except that Compound S was used instead of Compound 133. Luminous efficiency was measured when this device was driven at a constant current at room temperature with an emission luminance of 300 (cd / m 2 ). In addition, initial luminance when driven at a current density of 12.5 mA / cm 2 and luminance after continuous driving for 100 hours in an environment of 30 ° C. were measured. The results are shown in Table 10.
  • Example 142 Compound Q was vacuum-deposited on a glass plate with an ITO electrode to obtain a 60 nm-thick hole injection layer. Next, Compound H and Exemplary Compound 131 were co-evaporated at a composition ratio of 3: 100 to form a light-emitting layer having a thickness of 40 nm. Further, TPBI was deposited to form an electron injection layer having a thickness of 40 nm. On top of that, a cathode was formed by vapor deposition of 1 nm of lithium fluoride and 100 nm of Al to obtain an organic EL device.
  • Examples 143-159 A device was prepared in the same manner as in Example 142 except that the compound in Table 11 was used instead of the compound 131.
  • the luminous efficiency was 5 cd / A or more.
  • initial luminance when driven at a current density of 12.5 mA / cm 2 and luminance after continuous driving for 100 hours in an environment of 30 ° C. were measured. The results are shown in Table 11.
  • Comparative Examples 10-11 A device was prepared in the same manner as in Example 142 except that Compound S (Comparative Example 10) and the following Compound V (Comparative Example 11) were used instead of Compound 131. Luminous efficiency was measured when this device was driven at a constant current at room temperature with an emission luminance of 300 (cd / m 2 ). In addition, initial luminance when driven at a current density of 12.5 mA / cm 2 and luminance after continuous driving for 100 hours in an environment of 30 ° C. were measured. The results are shown in Table 11.
  • Example 160 Compound T was vacuum-deposited on a glass plate with an ITO electrode to obtain a 65 nm-thick hole injection layer. Next, Compound J and Compound 132 were co-evaporated at a composition ratio of 3: 100 to form a light emitting layer having a thickness of 35 nm. Further, TPBI was deposited to form an electron injection layer having a thickness of 30 nm. On top of that, a cathode was formed by vapor deposition of 1 nm of lithium fluoride and 100 nm of Al to obtain an organic EL device.
  • Examples 161-175 A device was prepared in the same manner as in Example 160 except that the compound in Table 12 was used instead of the compound 132.
  • the light emission efficiency is 4 cd / A or more, and when the elements are driven at a current density of 12.5 mA / cm 2 .
  • the luminance after each driving was measured. The results are shown in Table 12.
  • Comparative Examples 12-13 A device was prepared in the same manner as in Example 160 except that Compound S (Comparative Example 12) and Compound V (Comparative Example 13) were used instead of Compound 132. Luminous efficiency was measured when this device was driven at a constant current at room temperature with an emission luminance of 300 (cd / m 2 ). In addition, the initial luminance when driven at a current density of 12.5 mA / cm 2 , and continuous driving for 100 hours in an environment of 30 ° C., followed by continuous driving for 24 hours in an environment of 100 ° C., after each driving The brightness of was measured. The results are shown in Table 12.
  • Example 176 Compound K was vapor-deposited on a glass plate with an ITO electrode to form a hole injection layer having a thickness of 70 nm.
  • the compound 133 of Table 1 and the compound L were co-evaporated with the composition ratio of 100: 8, and the light emitting layer with a film thickness of 60 nm was formed.
  • Balq is vapor-deposited to form a 15 nm-thick hole blocking layer, and then Alq3 is vacuum-deposited thereon to form an electron-injecting layer having a thickness of 40 nm.
  • An electrode was formed by vapor-depositing 1 nm and then 200 nm of Al to obtain an organic EL device. When this device was driven at a constant current at room temperature with an emission luminance of 300 (cd / m 2 ), it emitted blue light and its luminous efficiency was 10.3 cd / A.
  • Examples 177-181 A device was prepared in the same manner as in Example 176 except that the compound in Table 13 was used instead of the compound 133. When these devices were driven at a constant current at room temperature with an emission luminance of 300 (cd / m 2 ), the luminous efficiency was 9 cd / A or more. The results are shown in Table 8.
  • Example 182 PEDOT / PSS (poly (3,4-ethylenedioxy) -2,5-thiophene / polystyrene sulfonic acid, BAYTRON P VP CH8000 manufactured by Bayer) manufactured on a cleaned glass plate with an ITO electrode by spin coating A hole injection layer having a film thickness of 60 nm was obtained. Next, 60% of PVK (polyvinylcarbazole), 5% of compound 183, and 36% of electron transport material (compound N) were dissolved in toluene at a concentration of 2.0 wt%, and light emission with a film thickness of 50 nm was performed by spin coating. A layer was obtained.
  • PVK polyvinylcarbazole
  • compound N electron transport material
  • Example 183 PEDOT / PSS (poly (3,4-ethylenedioxy) -2,5-thiophene / polystyrene sulfonic acid, BAYTRON P VP CH8000 manufactured by Bayer) manufactured on a cleaned glass plate with an ITO electrode by spin coating A hole injection layer having a film thickness of 60 nm was obtained. Next, 60% of PVK (polyvinylcarbazole), 5% of compound 218 and 35% of electron transport material (compound O) were dissolved in toluene at a concentration of 2.0 wt%, and light emission with a film thickness of 60 nm was performed by spin coating. A layer was obtained.
  • PVK polyvinylcarbazole
  • compound O electron transport material
  • Example 184 On the washed glass plate with an ITO electrode, the compound 278 was vacuum deposited to obtain a hole injection layer having a thickness of 40 nm. Subsequently, the compound (A) was vacuum-deposited to obtain a 40 nm hole transport layer. Furthermore, Alq3 is vacuum-deposited to form an electron-injection-type light-emitting layer having a thickness of 40 nm, and then an electrode is formed by first depositing 1 nm of lithium fluoride and then 200 nm of Al to form an organic EL device. It was. When this device was subjected to an energization test, yellow light emission with a maximum light emission luminance of 1960 cd / m 2 was obtained.
  • Example 185 Compound Q was deposited on a glass plate with an ITO electrode to form a 40 nm-thick hole injection layer, and then compound 218 was deposited to form a 40 nm-thick hole transport layer. Next, Alq3 was deposited to form an electron injecting light emitting layer having a thickness of 30 nm, and an electrode was formed thereon by vacuum deposition of 1 nm of lithium fluoride and 200 nm of Al, thereby obtaining an organic EL device. When an energization test was performed on this device, yellow light emission with a maximum light emission luminance of 1670 cd / m 2 was obtained.
  • Example 186 Compound Q was vacuum deposited on a glass plate with an ITO electrode to obtain a hole injection layer having a thickness of 70 nm. Next, Alq3 was deposited to form a light emitting layer with a thickness of 30 nm. Further, the compound 208 was deposited to form an electron injection layer having a thickness of 30 nm. On top of that, a cathode was formed by vapor deposition of 1 nm of lithium fluoride and 100 nm of Al to obtain an organic EL device. When this device was subjected to an energization test, yellow light emission with a maximum light emission luminance of 1490 cd / m 2 was obtained.
  • Example 187 A device was prepared in the same manner as in Example 186 except that compound 226 was used instead of compound 208. When this device was subjected to an energization test, yellow light emission with a maximum light emission luminance of 1620 cd / m 2 was obtained.
  • Example 188 ⁇ -NPD was vacuum-deposited on the cleaned glass plate with an ITO electrode to obtain a hole injection layer having a thickness of 60 nm. Subsequently, the compound 306 was vacuum-deposited and the light emitting layer with a film thickness of 30 nm was obtained. Further, TPBI was vacuum-deposited to form an electron injection layer having a film thickness of 30 nm, and an electrode was formed thereon by first depositing 1 nm of lithium fluoride and then 150 nm of Al, thereby obtaining an organic EL device. When this device was driven at a constant current at room temperature with an emission luminance of 300 (cd / m 2 ), it emitted blue light and had a light emission efficiency of 2.9 cd / A. In addition, initial luminance when driven at a current density of 12.5 mA / cm 2 and luminance after continuous driving for 100 hours in an environment of 30 ° C. were measured. The results are shown in Table 14.
  • Examples 189-204 A device was produced in the same manner as in Example 188 except that a light emitting layer was produced using the compounds shown in Table 14 instead of the compound 306. The efficiency was measured when this device was driven at a constant current at room temperature with an emission luminance of 300 (cd / m 2 ). In addition, initial luminance when driven at a current density of 12.5 mA / cm 2 and luminance after continuous driving for 100 hours in an environment of 30 ° C. were measured. The results are shown in Table 14.
  • Comparative Example 14 A device was produced in the same manner as in Example 188 except that a light emitting layer was produced using the compound W shown below instead of the compound 306. The efficiency was measured when this device was driven at a constant current at room temperature with an emission luminance of 300 (cd / m 2 ). In addition, initial luminance when driven at a current density of 12.5 mA / cm 2 and luminance after continuous driving for 100 hours in an environment of 30 ° C. were measured. The results are shown in Table 14.
  • Example 205 Compound Q was vacuum deposited on a glass plate with an ITO electrode to obtain a hole injection layer having a thickness of 80 nm. Next, the exemplified compound 308 and the compound R in Table 1 were co-evaporated at a composition ratio of 3: 100 to form a light emitting layer having a thickness of 35 nm. Further, TPBI was deposited to form an electron injection layer having a thickness of 35 nm. On top of that, a cathode was formed by vapor deposition of 1 nm of lithium fluoride and 100 nm of Al to obtain an organic EL device.
  • Examples 206-220 A device was prepared in the same manner as in Example 205 except that the compound shown in Table 15 was used instead of the exemplified compound 308.
  • the emission color was blue, and the emission efficiency was 5 cd / A or more.
  • initial luminance when driven at a current density of 12.5 mA / cm 2 and luminance after continuous driving for 100 hours in an environment of 30 ° C. were measured. The results are shown in Table 15.
  • Comparative Examples 15-16 A device was prepared in the same manner as in Example 205 except that Compound W (Comparative Example 15) and the following Compound X (Comparative Example 16) were used instead of Compound 308. Luminous efficiency was measured when these devices were driven at a constant current at room temperature with an emission luminance of 300 (cd / m 2 ). In addition, initial luminance when driven at a current density of 12.5 mA / cm 2 and luminance after continuous driving for 100 hours in an environment of 30 ° C. were measured. The results are shown in Table 15.
  • Example 221 Compound T was vacuum deposited on a glass plate with an ITO electrode to obtain a hole injection layer having a thickness of 60 nm. Next, Compound R and Exemplary Compound 307 were co-evaporated at a weight composition ratio of 100: 3 to form a light emitting layer having a thickness of 30 nm. Further, Compound B was deposited to form an electron injection layer having a thickness of 30 nm. A cathode was formed thereon by vapor deposition of 1 nm of Li 2 O and 100 nm of Al to obtain an organic EL device.
  • Examples 222 to 237 A device was prepared in the same manner as in Example 221 except that the compounds shown in Table 16 were used instead of the compound 307.
  • the emission color is blue
  • the emission efficiency is 5 cd / A or more
  • the current density is 12.5 mA /
  • the initial luminance when driven at cm 2 and the luminance after continuous driving for 100 hours in an environment of 30 ° C. were measured. The results are shown in Table 16.
  • Comparative Example 17 A device was prepared in the same manner as in Example 221 except that Compound X was used instead of Compound 307. Luminous efficiency was measured when this device was driven at a constant current at room temperature with an emission luminance of 300 (cd / m 2 ). In addition, initial luminance when driven at a current density of 12.5 mA / cm 2 and luminance after continuous driving for 100 hours in an environment of 30 ° C. were measured. The results are shown in Table 16.
  • Example 238 Compound Q was vacuum-deposited on a glass plate with an ITO electrode to obtain a 60 nm-thick hole injection layer. Next, Compound H and Exemplary Compound 306 were co-evaporated at a composition ratio of 3: 100 to form a 40 nm thick light emitting layer. Further, TPBI was deposited to form an electron injection layer having a thickness of 40 nm. On top of that, a cathode was formed by vapor deposition of 1 nm of lithium fluoride and 100 nm of Al to obtain an organic EL device.
  • Examples 239 to 251 A device was prepared in the same manner as in Example 238 except that the compound shown in Table 17 was used instead of the compound 306.
  • the luminous efficiency was 5 cd / A or more.
  • initial luminance when driven at a current density of 12.5 mA / cm 2 and luminance after continuous driving for 100 hours in an environment of 30 ° C. were measured. The results are shown in Table 17.
  • Comparative Examples 18-19 A device was prepared in the same manner as in Example 238 except that Compound X (Comparative Example 18) and the following Compound Y (Comparative Example 19) were used instead of Compound 306. Luminous efficiency was measured when this device was driven at a constant current at room temperature with an emission luminance of 300 (cd / m 2 ). In addition, initial luminance when driven at a current density of 12.5 mA / cm 2 and luminance after continuous driving for 100 hours in an environment of 30 ° C. were measured. The results are shown in Table 17.
  • Example 252 Compound T was vacuum-deposited on a glass plate with an ITO electrode to obtain a 65 nm-thick hole injection layer. Next, Compound J and Compound 307 were co-evaporated at a composition ratio of 3: 100 to form a light emitting layer having a thickness of 35 nm. Further, TPBI was deposited to form an electron injection layer having a thickness of 30 nm. On top of that, a cathode was formed by vapor deposition of 1 nm of lithium fluoride and 100 nm of Al to obtain an organic EL device.
  • Examples 253 to 266 A device was prepared in the same manner as in Example 252 except that the compound shown in Table 18 was used instead of the compound 307.
  • the light emission efficiency is 4 cd / A or more, and when the elements are driven at a current density of 12.5 mA / cm 2 .
  • the luminance after each driving was measured. The results are shown in Table 18.
  • Comparative Examples 20-21 A device was prepared in the same manner as in Example 252 except that Compound X (Comparative Example 20) and Compound Y (Comparative Example 21) were used instead of Compound 307. Luminous efficiency was measured when this device was driven at a constant current at room temperature with an emission luminance of 300 (cd / m 2 ). In addition, the initial luminance when driven at a current density of 12.5 mA / cm 2 , and continuous driving for 100 hours in an environment of 30 ° C., followed by continuous driving for 24 hours in an environment of 100 ° C., after each driving The brightness of was measured. The results are shown in Table 18.
  • Example 267 Compound K was deposited on a glass plate with an ITO electrode to form a hole injection layer having a thickness of 60 nm.
  • the compound 315 of Table 1 and the compound L were co-evaporated with the composition ratio of 100: 9, and the light emitting layer with a film thickness of 50 nm was formed.
  • Balq is vapor-deposited to form a 10 nm-thick hole blocking layer, and then Alq3 is vacuum-deposited thereon to form a 50-nm-thick electron injection layer.
  • An electrode was formed by vapor-depositing 1 nm and then 200 nm of Al to obtain an organic EL device. When this device was driven at a constant current at room temperature with an emission luminance of 300 (cd / m 2 ), it emitted blue light and its luminous efficiency was 11.4 cd / A.
  • Examples 268-276 A device was prepared in the same manner as in Example 267 except that the compound shown in Table 19 was used instead of the compound 315. When these devices were driven at a constant current at room temperature with an emission luminance of 300 (cd / m 2 ), the luminous efficiency was 9 cd / A or more. The results are shown in Table 19.
  • Example 277 PEDOT / PSS (poly (3,4-ethylenedioxy) -2,5-thiophene / polystyrene sulfonic acid, BAYTRON P VP CH8000 manufactured by Bayer) manufactured on a cleaned glass plate with an ITO electrode by spin coating A hole injection layer having a thickness of 50 nm was obtained. Next, 60% of PVK (polyvinylcarbazole), 5% of compound 373 and 36% of electron transport material (compound N) were dissolved in toluene at a concentration of 2.5 wt%, and light emission with a film thickness of 40 nm was performed by spin coating. A layer was obtained.
  • PVK polyvinylcarbazole
  • compound N electron transport material
  • Example 278 PEDOT / PSS (poly (3,4-ethylenedioxy) -2,5-thiophene / polystyrene sulfonic acid, BAYTRON P VP CH8000 manufactured by Bayer) manufactured on a cleaned glass plate with an ITO electrode by spin coating A hole injection layer having a thickness of 50 nm was obtained. Next, 60% PVK (polyvinylcarbazole), 5% compound 381 and 35% electron transport material (compound O) were dissolved in toluene at a concentration of 2.5 wt%, and light emission with a film thickness of 50 nm was performed by spin coating. A layer was obtained.
  • PVK polyvinylcarbazole
  • compound O electron transport material
  • Example 279 On the cleaned glass plate with an ITO electrode, the compound 310 of the present invention was vacuum-deposited to obtain a 50 nm-thick hole injection layer. Compound A was then vacuum evaporated to obtain a 50 nm hole transport layer. Further, Alq3 is vacuum-deposited to form an electron-injection type light-emitting layer having a film thickness of 50 nm, and then an electrode is formed by first depositing 1 nm of lithium fluoride and then 200 nm of Al to form an electrode. It was. When an energization test was performed on this device, yellow light emission with a maximum light emission luminance of 2570 (cd / m 2 ) was obtained.
  • Examples 280-282 A device was produced in the same manner as in Example 279 except that the compound shown in Table 20 was used instead of the compound 310.
  • Table 20 shows the maximum light emission luminance when conducting an energization test on these elements.
  • Example 283 Compound Q was deposited on a glass plate with an ITO electrode to form a 30 nm-thick hole injection layer, and then compound 312 was deposited to form a 50 nm-thick hole transport layer. Next, Alq3 was deposited to form an electron injecting light emitting layer having a thickness of 40 nm, and an electrode was formed thereon by vacuum deposition of 1 nm of lithium fluoride and 200 nm of Al, thereby obtaining an organic EL device. When an energization test was performed on this device, yellow light emission with a maximum light emission luminance of 1950 (cd / m 2 ) was obtained.
  • Examples 284-286 A device was prepared in the same manner as in Example 283 except that the compound shown in Table 21 was used instead of the compound 312. Table 21 shows the maximum light emission luminance when conducting an energization test on these elements.
  • Example 287 Compound Q was vacuum deposited on a glass plate with an ITO electrode to obtain a hole injection layer having a thickness of 40 nm. Next, Alq3 was deposited to form a light-emitting layer having a thickness of 40 nm. Further, a compound 311 was deposited to form an electron injection layer having a thickness of 30 nm. On top of that, a cathode was formed by vapor deposition of 1 nm of lithium fluoride and 100 nm of Al to obtain an organic EL device. When this device was subjected to a current test, yellow light emission with a maximum light emission luminance of 1690 (cd / m 2 ) was obtained.
  • Examples 288-293 A device was prepared in the same manner as in Example 287 except that the compound shown in Table 22 was used instead of the compound 311.
  • Table 22 shows the maximum light emission luminance when conducting an energization test on these elements.
  • the organic EL device using the organic EL device material of the present invention can achieve improved luminous efficiency and longer life.

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Abstract

L'invention porte sur une matière pour dispositif électroluminescent organique, qui est caractérisée par le fait qu'elle est composée d'un composé représenté par la formule générale [1]. (Dans la formule, Ar1 et Ar2 représentent indépendamment un groupe hydrocarboné aromatique divalent substitué ou non substitué ou un groupe hétérocyclique aromatique divalent substitué ou non substitué; Ar3 représente un groupe hydrocarboné aromatique fusionné substitué ou non substitué ou un groupe hétérocyclique aromatique fusionné substitué ou non substitué; Ar4 représente un atome d'hydrogène, un groupe hydrocarboné aromatique substitué ou non substitué ou un groupe hétérocyclique aromatique substitué ou non substitué; X représente S, O ou N-Ar5 (où Ar5 représente un groupe hydrocarboné aromatique substitué ou non substitué ou un groupe hétérocyclique aromatique substitué ou non substitué); et R1 et R2 représentent indépendamment un atome d'hydrogène, un groupe alkyle substitué ou non substitué, un groupe hydrocarboné aromatique substitué ou non substitué, un groupe hétérocyclique aromatique substitué ou non substitué, un groupe alcoxy substitué ou non substitué ou un groupe aryloxy substitué ou non substitué. À cet égard, R1 et R2 peuvent se combiner ensemble pour former un noyau.)
PCT/JP2009/053023 2008-02-22 2009-02-20 Matière pour dispositif électroluminescent organique et dispositif électroluminescent organique WO2009104733A1 (fr)

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US20120126217A1 (en) * 2009-10-16 2012-05-24 Idemitsu Kosan Co. Ltd. Fluorene-containing aromatic compound, material for organic electroluminescent element, and organic electroluminescent element using same
JP2013234183A (ja) * 2012-05-03 2013-11-21 Samsung Display Co Ltd 縮合環化合物及びそれを含んだ有機発光素子
KR101585297B1 (ko) 2013-09-03 2016-01-13 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
CN107759504A (zh) * 2017-10-13 2018-03-06 北京理工大学 一种固液态均具较强荧光的双相有机荧光材料及制备方法
CN110452226A (zh) * 2019-08-05 2019-11-15 北京大学深圳研究生院 一种基于吡咯衍生物的有机蓝光荧光材料与蓝光器件
WO2023140173A1 (fr) * 2022-01-21 2023-07-27 日鉄ケミカル＆マテリアル株式会社 Matériau pour élément de conversion photoélectrique destiné à l'imagerie, et élément de conversion photoélectrique

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JP2013234183A (ja) * 2012-05-03 2013-11-21 Samsung Display Co Ltd 縮合環化合物及びそれを含んだ有機発光素子
EP2666768A2 (fr) * 2012-05-03 2013-11-27 Samsung Display Co., Ltd. Composé cyclique condensé et diode électroluminescente organique le comprenant
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US10249824B2 (en) 2012-05-03 2019-04-02 Samsung Display Co., Ltd. Condensed-cyclic compound and organic light-emitting diode comprising the same
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CN107759504A (zh) * 2017-10-13 2018-03-06 北京理工大学 一种固液态均具较强荧光的双相有机荧光材料及制备方法
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WO2023140173A1 (fr) * 2022-01-21 2023-07-27 日鉄ケミカル＆マテリアル株式会社 Matériau pour élément de conversion photoélectrique destiné à l'imagerie, et élément de conversion photoélectrique

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