WO2016002864A1 - Composé triazine, son procédé de production, et son utilisation - Google Patents

Composé triazine, son procédé de production, et son utilisation Download PDF

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WO2016002864A1
WO2016002864A1 PCT/JP2015/069078 JP2015069078W WO2016002864A1 WO 2016002864 A1 WO2016002864 A1 WO 2016002864A1 JP 2015069078 W JP2015069078 W JP 2015069078W WO 2016002864 A1 WO2016002864 A1 WO 2016002864A1
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group
pyridyl
phenyl
atom
phenyl group
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Japanese (ja)
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新井信道
服部一希
岡祐児
野村桂甫
田中剛
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Tosoh Corp
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Tosoh Corp
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Priority claimed from JP2014178231A external-priority patent/JP6421502B2/ja
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Priority to KR1020167036957A priority Critical patent/KR20170023025A/ko
Priority to CN201580043586.2A priority patent/CN106573912A/zh
Publication of WO2016002864A1 publication Critical patent/WO2016002864A1/fr
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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms

Definitions

  • the inventors of the present invention have high heat resistance in the film quality of a triazine compound bonded with a diarylpyridyl group described later, and organic electroluminescence using the compound as an electron transport material It has been found that the device has a lower voltage, longer life, or higher luminous efficiency than the case where a conventionally known material is used, and the present invention has been completed.
  • a triazine compound represented by the following general formula (1) [2] Ar 2 and Ar 3 are each independently an optionally linked aromatic hydrocarbon group having 6 to 24 carbon atoms and / or a condensed ring having only 3 to 25 carbon atoms, A nitrogen-containing heteroaromatic group which may be condensed or a C3-C25 linkage and / or a condensed ring composed of an atom selected from the group consisting of atoms of H, C, O and S The triazine compound according to [1], which may be a heteroaromatic group.
  • Ar 2 and Ar 3 are each independently a phenyl group, tolyl group, dimethylphenyl group, biphenyl group, naphthylphenyl group, phenanthrylphenyl group, pyridylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, naphthyl group
  • the triazine compound according to [1] which is a pyridyl group, a benzothienyl group, a benzofuryl group, a phenanthryl group, an anthryl group, a dibenzothienyl group, or a dibenzofuryl group.
  • Ar 1 each independently represents a phenyl group or a naphthyl group (these groups may be substituted with a fluorine atom, a methyl group, or a phenyl group).
  • Ar 2 and Ar 3 are each independently a linkage having 6 to 24 carbon atoms and / or an aromatic hydrocarbon group which may be condensed, a linkage having 3 to 25 carbon atoms composed of only a 6-membered ring, and A nitrogen-containing heteroaromatic group which may be condensed or a C3-C25 linkage and / or a condensed ring composed of an atom selected from the group consisting of atoms of H, C, O and S Or a heteroaromatic group which may be substituted (these groups may be substituted with a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms).
  • the present invention relates to the above-mentioned triazine compounds (1), a method for producing them, and a material for an organic electroluminescent device containing the compounds.
  • a phenyl group substituted with a methyl group or a naphthyl group in Ar 1 is not particularly limited, but a tolyl group, a methylnaphthyl group, a dimethylphenyl group, a dimethylnaphthyl group, and the like are preferable examples.
  • Ar 1 is preferably a phenyl group, a naphthyl group, or a biphenyl group independently from the viewpoint of excellent electron transporting material properties, and more preferably a phenyl group from the viewpoint of easy synthesis.
  • Ar 2 and Ar 3 may be the same or different.
  • the aromatic hydrocarbon group that may be linked and / or condensed with 6 to 24 carbon atoms in Ar 2 and Ar 3 is not particularly limited, but includes a phenyl group, a biphenyl group, a terphenyl group, Quarterphenyl group, naphthylphenyl group, phenanthrylphenyl group, anthrylphenyl group, pyrenylphenyl group, triphenylphenyl group, chrysenylphenyl group, fluoranthenylphenyl group, acenaphthylphenyl group, fluorenylphenyl group Group, naphthylbiphenyl group, naphthyl group, phenylnaphthyl group, biphenylnaphthyl group, phenanthrylnaphthyl group, anthrylnaphthyl group, phenanthryl group, phenylphenanthryl group, naphth
  • the nitrogen-containing heteroaromatic group which may be linked and / or condensed with 3 to 25 carbon atoms composed of only a 6-membered ring in Ar 2 and Ar 3 is not particularly limited.
  • heteroaromatic group having 3 to 25 carbon atoms and / or a condensed ring composed of atoms selected from the group consisting of H, C, O and S in Ar 2 and Ar 3 include Although not particularly limited, thienyl group, furyl group, bithienyl group, bifuryl group, benzothienyl group, benzofuryl group, dibenzothienyl group, dibenzofuryl group, thienylphenyl group, furylphenyl group, bithienylphenyl group, bithienyl group, Furylphenyl group, benzothienylphenyl group, benzofurylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, thienylbiphenyl group, furylbiphenyl group, benzothienylbiphenyl group, benzofurylbiphenyl group, dibenzothienylbiphenyl group,
  • the alkoxy group having 1 to 4 carbon atoms in Ar 2 and Ar 3 is not particularly limited, but is a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, or a t-butoxy group. Groups and the like are mentioned as preferred examples.
  • Ar 2 and Ar 3 are each independently composed of an aromatic hydrocarbon group having 6 to 24 carbon atoms and / or a condensed ring, or a 6-membered ring, in that it has excellent electron transporting material properties.
  • 3 to 25 carbon atoms composed of atoms selected from the group consisting of nitrogen-containing heteroaromatic groups that may be linked and / or condensed and / or H, C, O, and S It is preferably a heteroaromatic group (which may be substituted with an alkyl group having 1 to 4 carbon atoms) which may be linking to 25 and / or optionally condensed.
  • a ruphenyl group More preferred are a ruphenyl group, a naphthyl group, a pyridyl group, a benzothienyl group, a benzofuryl group, a phenanthryl group, an anthryl group, a dibenzothienyl group, or a dibenzofuryl group, and each independently a phenyl group, a tolyl group, a dimethylphenyl group.
  • a biphenyl group preferably a naphthylphenyl group, a phenanthrylphenyl group, a pyridylphenyl group, a dibenzothienylphenyl group, a dibenzofurylphenyl group, a naphthyl group, a pyridyl group, or a phenanthryl group.
  • Ar 2 and / or Ar 3 are each independently a fragrance that is linked to and / or condensed from 10 to 24 carbon atoms from the viewpoint of excellent electron transporting material properties.
  • Biphenyl, naphthylphenyl, phenanthrylphenyl, fluoranthenylphenyl, pyridylphenyl, quinolylphenyl, thienylphenyl, furylfur Nyl group, benzothienylphenyl group, benzofurylphenyl group, dibenzothienylphenyl group, dibenzofurylphenyl group, naphthyl group, benzothienyl group, benzofuryl group, phenanthryl group, anthryl group, dibenzothienyl group, or dibenzofuryl group Are more preferable, and a biphenyl group, a naphthylphenyl group, a phenanthrylphenyl group, a pyridylphenyl group, a dibenzothienylphenyl group, a dibenzofurylphenyl group, a naphthyl group, or a phenanthryl
  • Ar 2 And Ar 3 Specific examples of these include, but are not limited to, phenyl group, p-tolyl group, m-tolyl group, o-tolyl group, 2,4-dimethylphenyl group, 3,5-dimethylphenyl group, mesityl group 2-ethylphenyl group, 3-ethylphenyl group, 4-ethylphenyl group, 2,4-diethylphenyl group, 3,5-diethylphenyl group, 2-propylphenyl group, 3-propylphenyl group, 4-propyl Phenyl group, 2,4-dipropylphenyl group, 3,5-dipropylphenyl group, 2-isopropylphenyl group, 3-isopropylphenyl group, 4-isopropylphenyl group, 2,4-diisopropylphenyl group, 3,5 -Diisopropylphenyl group, 2-butylphenyl group, 3-buty
  • R 5 , R 6 and R 7 each independently represents an alkyl group having 1 to 4 carbon atoms.
  • the alkyl group having 1 to 4 carbon atoms in R 5 , R 6 and R 7 is not particularly limited, but is methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, or t-butyl group.
  • a group etc. are mentioned as a preferable example. Of these substituents, a methyl group is more preferable in terms of excellent electron transporting material characteristics.
  • n 0 or 1.
  • p represents 0, 1, 2, 3 or 4.
  • R 5 may be different from each other.
  • q represents 0, 1, 2, 3 or 4.
  • R 6 may be different from each other.
  • r represents 0, 1 or 2.
  • two R 7 may be different from each other.
  • P, q, and r are each independently preferably 0 or 1, and more preferably all 0, because they are excellent in electron transporting material properties.
  • this compound When this compound is used as a part of the components of the organic electroluminescence device, effects such as high luminous efficiency, long life, and low voltage can be obtained. In particular, this effect is prominent when used as an electron transport layer.
  • particularly preferable compounds include the following (A-1) to (A-1669), but the present invention is not limited thereto. .
  • the light emitting layer in an organic electroluminescent element refers to a layer that emits light when a current is passed through an electrode composed of a cathode and an anode. Specifically, it refers to a layer containing a fluorescent compound that emits light when an electric current is passed through an electrode composed of a cathode and an anode.
  • an organic electroluminescent element has a structure in which a light emitting layer is sandwiched between a pair of electrodes.
  • the organic electroluminescence device of the present invention has a structure in which a hole transport layer, an electron transport layer, an anode buffer layer, a cathode buffer layer, and the like are provided in addition to the light emitting layer as required, and are sandwiched between a cathode and an anode.
  • a hole transport layer, an electron transport layer, an anode buffer layer, a cathode buffer layer, and the like are provided in addition to the light emitting layer as required, and are sandwiched between a cathode and an anode.
  • Specific examples include the structures shown below.
  • anode / light emitting layer / cathode ii) Anode / hole transport layer / light emitting layer / cathode (iii) Anode / light emitting layer / electron transport layer / cathode (iv) anode / hole transport layer / light emitting layer / electron Transport layer / cathode (v) anode / anode buffer layer / hole transport layer / light emitting layer / electron transport layer / cathode buffer layer / cathode
  • a method for forming the light emitting layer for example, there is a method of forming a thin film by a known method such as a vapor deposition method, a spin coating method, a casting method, or an LB method.
  • the film thickness of the light emitting layer thus formed is not particularly limited and can be appropriately selected according to the situation, but is usually in the range of 5 nm to 5 ⁇ m.
  • electrons injected from the cathode and transported from the electron injection layer and / or the electron transport layer to the light-emitting layer are generated by the electron barrier existing at the interface between the light-emitting layer and the hole injection layer or the hole transport layer. It accumulates at the interface in the light emitting layer without leaking into the injection layer or the hole transport layer, resulting in an element with excellent light emitting performance such as improved luminous efficiency.
  • the hole injecting material and the hole transporting material have either hole injection or transport or electron barrier properties, and may be either organic or inorganic.
  • Examples of the hole injection material and hole transport material include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazoles.
  • Derivatives styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers, particularly thiophene oligomers.
  • the hole injecting material and the hole transporting material those described above can be used, and porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds, particularly aromatic tertiary amine compounds can be used. preferable.
  • aromatic tertiary amine compounds and styrylamine compounds include N, N, N ′, N′-tetraphenyl-4,4′-diaminophenyl, N, N′-diphenyl-N, N ′.
  • inorganic compounds such as p-type-Si and p-type-SiC can be used as the hole injection material and the hole transport material.
  • the hole injection layer and the hole transport layer are formed by thinning the hole injection material and the hole transport material by a known method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method. Can be formed.
  • the film thickness of the hole injection layer and the hole transport layer is not particularly limited, but is usually about 5 nm to 5 ⁇ m.
  • the hole injection layer and hole transport layer may have a single layer structure composed of one or more of the above materials, or may have a multilayer structure composed of a plurality of layers having the same composition or different compositions.
  • the electron transport layer contains a triazine compound represented by the general formula (1).
  • the electron transport layer may be formed by forming the triazine compound represented by the general formula (1) by a known thin film forming method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method. it can.
  • the thickness of the electron transport layer is not particularly limited, but is usually selected in the range of 5 nm to 5 ⁇ m.
  • this electron transport layer contains a triazine compound represented by the general formula (1), may contain a conventionally known electron transport material, and may have a single-layer structure composed of one kind or two or more kinds. Alternatively, a laminated structure composed of a plurality of layers having the same composition or different compositions may be used.
  • the substrate that is preferably used in the organic electroluminescent device of the present invention is not particularly limited in the type of glass, plastic, etc., and is not particularly limited as long as it is transparent.
  • Examples of the substrate preferably used in the organic electroluminescence device of the present invention include glass, quartz, and a light transmissive plastic film.
  • the light transmissive plastic film examples include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyetheretherketone, polyphenylene sulfide, polyarylate, polyimide, and polycarbonate (PC). And a film made of cellulose triacetate (TAC), cellulose acetate propionate (CAP), or the like.
  • a thin film made of a desired electrode material for example, an anode material
  • a suitable substrate by a method such as vapor deposition or sputtering so as to have a film thickness of 1 ⁇ m or less, preferably in the range of 10 to 200 nm.
  • An anode is produced.
  • a thin film comprising a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer / electron injection layer, which is a device material, is formed thereon.
  • a buffer layer (electrode interface layer) may exist between the anode and the light emitting layer or the hole injection layer and between the cathode and the light emitting layer or the electron injection layer.
  • a layer having other functions may be laminated as necessary.
  • a functional layer such as a hole blocking layer or an electron blocking layer may be provided.
  • an electrode material made of a metal, an alloy, an electrically conductive compound or a mixture thereof having a large work function (4 eV or more) is preferably used as the anode in the organic electroluminescence device.
  • an electrode material made of a metal, an alloy, an electrically conductive compound or a mixture thereof having a large work function (4 eV or more) is preferably used.
  • Specific examples of such an electrode substance include a conductive transparent material such as a metal such as Au, CuI, indium tin oxide (ITO), SnO 2 , and ZnO.
  • the anode may be formed by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering, and a pattern having a desired shape may be formed by photolithography, or the pattern may be formed through a mask having a desired shape at the time of vapor deposition or sputtering. May be formed.
  • a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function value than this from the viewpoint of durability against electron injecting and oxidation for example, a magnesium / silver mixture, magnesium
  • An aluminum / aluminum mixture, a magnesium / indium mixture, an aluminum / aluminum oxide (Al 2 O 3 ) mixture, a lithium / aluminum mixture, and the like are preferable.
  • the cathode can be produced by forming a thin film from these electrode materials by a method such as vapor deposition or sputtering.
  • the organic electroluminescence device of the present invention may be used as a kind of lamp for illumination or exposure light source, a projection device for projecting an image, or a display for directly viewing a still image or a moving image. It may be used as a device (display).
  • the driving method may be either a simple matrix (passive matrix) method or an active matrix method.
  • the triazine compound (1) of the present invention has the following reaction formula (11) in the presence or absence of a base and in the presence of a palladium catalyst.
  • Each M independently represents ZnR 1 , MgR 2 , Sn (R 3 ) 3 or B (OR 4 ) 2 .
  • R ⁇ 1 > and R ⁇ 2 > represents a chlorine atom, a bromine atom, or an iodine atom each independently
  • R ⁇ 3 > represents a C1-C4 alkyl group or a phenyl group
  • R ⁇ 4 > is a hydrogen atom, carbon number 1 It represents an alkyl group or a phenyl group 4
  • B (oR 4) 2 two R 4 2 may be the same or different. Further, two R 4 may form a ring containing an oxygen atom and a boron atom together.
  • ZnR 1 and MgR 2 examples include ZnCl, ZnBr, ZnI, MgCl, MgBr, and MgI.
  • Compound (13) used in Reaction Formula (11), Compound (15) used in Reaction Formula (12), Compound (23) used in Reaction Formula (21), and Compound (23) used in Reaction Formula (22) 25) are disclosed in, for example, JP-A-2005-268199, [0105] to [0121], JP-A-2008-280330, [0061] to [0076], or JP-A-2001-335516, [0047] to [0082]. Can be produced in combination.
  • Examples of the compound (13) and the compound (23) include the following (B-1) to (B-56), but the present invention is not limited to these.
  • Compound (15) used in Reaction Formula (12) and Compound (25) used in Reaction Formula (22) are compounds obtained by replacing M in Compound (13) and Compound (23) with Y. It can be illustrated.
  • Y in the compound (12), the compound (15), the compound (22), and the compound (25) represents a leaving group, and is not particularly limited.
  • a chlorine atom, a bromine atom, an iodine atom, or a triflate may be used. Can be mentioned. Among these, a bromine atom or a chlorine atom is preferable in terms of a good reaction yield. However, it may be preferable to use triflate because of the availability of raw materials.
  • Step 11 is a method in which the compound (12) is reacted with the compound (13) in the presence or absence of a base in the presence of a palladium catalyst to obtain the triazine compound (11) of the present invention.
  • reaction conditions of general coupling reactions such as Suzuki-Miyaura reaction, Negishi reaction, Tamao-Kumada reaction, Stille reaction, etc., the target product can be obtained in high yield.
  • Examples of the palladium catalyst that can be used in “Step 11” include salts of palladium chloride, palladium acetate, palladium trifluoroacetate, palladium nitrate, and the like. Furthermore, ⁇ -allyl palladium chloride dimer, palladium acetylacetonate, tris (dibenzylideneacetone) dipalladium, dichlorobis (triphenylphosphine) palladium, tetrakis (triphenylphosphine) palladium and dichloro (1,1′-bis (diphenylphosphine). Examples include complex compounds such as fino) ferrocene) palladium.
  • a palladium complex having a tertiary phosphine as a ligand is more preferable in terms of a good reaction yield, is easily available, and a palladium complex having triphenylphosphine as a ligand is preferable in terms of a good reaction yield. Particularly preferred.
  • 2-dicyclohexylphosphino-2 ', 4', 6'-triisopropylbiphenyl or triphenylphosphine is preferable because it is easily available and the reaction yield is good.
  • the molar ratio of the tertiary phosphine to the palladium salt or complex compound is preferably 1:10 to 10: 1, and more preferably 1: 2 to 5: 1 from the viewpoint of good reaction yield.
  • Examples of the base that can be used in “Step 11” include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, lithium carbonate, cesium carbonate, potassium phosphate, sodium phosphate, sodium fluoride, potassium fluoride, fluoride. Examples thereof include cesium chloride, and potassium carbonate is preferable in terms of a good yield.
  • the molar ratio of base to compound (13) is preferably 1: 2 to 10: 1, and more preferably 1: 1 to 3: 1 in terms of good yield.
  • the molar ratio of the compound (12) and the compound (13) used in “Step 11” is preferably 1: 2 to 5: 1, and more preferably 1: 2 to 2: 1 in terms of a good yield.
  • Examples of the solvent that can be used in “Step 11” include water, dimethyl sulfoxide, dimethylformamide, tetrahydrofuran, 1,4-dioxane, dimethoxyethane, toluene, benzene, diethyl ether, ethanol, methanol, and xylene. You may use it combining suitably. It is desirable to use a mixed solvent of dioxane or tetrahydrofuran and water in terms of a good yield.
  • Compound (11) can be obtained by carrying out a normal treatment after completion of “Step 11”. If necessary, it may be purified by recrystallization, column chromatography or sublimation.
  • Step 11 “Step 12” can be applied by replacing Compound (12) with Compound (15) and Compound (13) with Compound (14).
  • Step 21 can be applied by replacing Compound (12) with Compound (22) and Compound (13) with Compound (23).
  • Step 22 can be applied by replacing Compound (12) with Compound (25) and Compound (13) with Compound (24).
  • the reaction conditions are not necessarily the same as those in “Step 11”.
  • purification may be performed by recrystallization, column chromatography, sublimation, or the like, if necessary.
  • the triazine compound (1) of the present invention can also be produced using a compound represented by the general formula (26).
  • Z 3 , Z 4 and Z 5 each independently represent a nitrogen atom or C—H. However, any one of Z 3 , Z 4 , and Z 5 represents a nitrogen atom, and the remaining two represent C—H.
  • X 1 and X 2 each independently represent a chlorine atom, a bromine atom, or an iodine atom. However, both X 1 and X 2 are not bromine atoms.
  • the triazine compound (1) of the present invention is prepared by the following reaction formula (23) in the presence or absence of a base and in the presence of a palladium catalyst.
  • Ar 1 represents the same substituent as described above.
  • Ar 4 is an aromatic hydrocarbon group that may be linked and / or condensed with 6 to 18 carbon atoms, or a linked and / or condensed ring with 3 to 19 carbon atoms that is composed of only a 6-membered ring.
  • X 1 and X 2 each independently represent a chlorine atom, a bromine atom, or an iodine atom. However, both X 1 and X 2 are not bromine atoms.
  • the triazine compound (1) of the present invention can be reacted with the reaction formula (26) in the presence of a palladium catalyst in the presence or absence of a base.
  • X 1 and X 2 each independently represent a chlorine atom, a bromine atom, or an iodine atom. However, both X 1 and X 2 are not bromine atoms. Among these, a bromine atom or a chlorine atom is preferable in terms of a good reaction yield. In order to improve the selectivity of the reaction, it is more preferable that X 1 and X 2 have different atoms.
  • Ar 4 are not particularly limited, but the same substituents as those specifically exemplified for Ar 2 can be exemplified.
  • the aromatic hydrocarbon group which may be connected and / or condensed having a carbon number greater than 18 or a connected and / or condensed ring having a carbon number greater than 20 composed of only a 6-membered ring.
  • reaction formula (23), reaction formula (24), reaction formula (25), reaction formula (26), reaction formula (27), and reaction formula (28), Suzuki-Miyaura reaction, Negishi reaction, Tamao-Kumada The target product can be obtained in good yield by carrying out general coupling reactions such as reactions and Stille reactions as many times as necessary under the general conditions.
  • Step 23 can be applied to the conditions listed in “Step 21” in which the compound (22) is replaced with the compound (26) and the compound (23) is replaced with the compound (28).
  • the reaction conditions are not necessarily the same as those in “Step 21”.
  • purification may be performed by recrystallization, column chromatography, sublimation or the like, if necessary.
  • Step 24 is applicable to the conditions listed in “Step 21” in which the compound (22) is replaced with the compound (29) and the compound (23) is replaced with the compound (30). However, the reaction conditions are not necessarily the same as those in “Step 21”. After completion of “Step 24”, it may be purified by recrystallization, column chromatography, sublimation or the like, if necessary.
  • Step 26 is applicable to the conditions listed in “Step 21” in which the compound (22) is replaced with the compound (32) and the compound (23) is replaced with the compound (28). However, the reaction conditions are not necessarily the same as those in “Step 21”. After completion of “Step 26”, purification may be performed by recrystallization, column chromatography, sublimation or the like, if necessary.
  • Step 27 among the conditions listed in “Step 21”, the conditions in which compound (23) is replaced with compound (33) can be applied. However, the reaction conditions are not necessarily the same as those in “Step 21”. After completion of “Step 27”, purification may be performed by recrystallization, column chromatography, sublimation or the like, if necessary.
  • Step 30 can be applied to the conditions listed in “Step 21” in which the compound (22) is replaced with the compound (32) and the compound (23) is replaced with the compound (28).
  • the reaction conditions are not necessarily the same as those in “Step 21”.
  • Step 31 among the conditions listed in “Step 21”, the conditions in which compound (23) is replaced with compound (36) can be applied. However, the reaction conditions are not necessarily the same as those in “Step 21”. After completion of “Step 31”, it may be purified by recrystallization, column chromatography, sublimation or the like, if necessary.
  • Step 32 is applicable to the conditions listed in “Step 21” in which the compound (22) is replaced with the compound (35) and the compound (23) is replaced with the compound (37). However, the reaction conditions are not necessarily the same as those in “Step 21”. After completion of “Step 32”, it may be purified by recrystallization, column chromatography, sublimation or the like, if necessary.
  • the triazine compound (1) of the present invention is suitably used as a material for an organic electroluminescence device.
  • the film-forming by a vacuum evaporation method is possible. Film formation by the vacuum evaporation method can be performed by using a general-purpose vacuum evaporation apparatus.
  • the vacuum degree of the vacuum chamber when forming a film by the vacuum deposition method is determined by taking into account the manufacturing tact time and manufacturing cost of manufacturing the organic electroluminescence device, and commonly used diffusion pumps, turbo molecular pumps, cryopumps, etc.
  • the deposition rate is preferably 0.005 to 1.0 nm / second, more preferably 0.01 to 1 nm / second, depending on the thickness of the film to be formed.
  • the triazine compounds (11) and (1) of the present invention have high solubility in chloroform, dichloromethane, 1,2-dichloroethane, chlorobenzene, toluene, ethyl acetate, tetrahydrofuran, or the like, a spin coat using a general-purpose apparatus. Film formation by the GOT method, inkjet method, cast method, dipping method or the like is also possible.
  • the typical structure of the organic electroluminescent element capable of obtaining the effects of the present invention includes a substrate, an anode, a hole injection layer, a hole transport layer light emitting layer, an electron transport layer, and a cathode.
  • the anode and cathode of the organic electroluminescent element are connected to a power source through an electrical conductor.
  • the organic electroluminescent device operates by applying a potential between the anode and the cathode. Holes are injected into the organic electroluminescent device from the anode, and electrons are injected into the organic electroluminescent device at the cathode.
  • the organic electroluminescent element is typically placed on a substrate, and the anode or cathode can be in contact with the substrate.
  • the electrode in contact with the substrate is called the lower electrode for convenience.
  • the lower electrode is an anode, but the organic electroluminescence device of the present invention is not limited to such a form.
  • the substrate may be light transmissive or opaque, depending on the intended emission direction. Light transmission properties are desirable for viewing electroluminescent emission through a substrate. Transparent glass or plastic is generally employed as such a substrate.
  • the substrate may be a composite structure including multiple material layers.
  • anode should pass or substantially pass the emission.
  • Common transparent anode (anode) materials used in the present invention are indium-tin oxide (ITO), indium-zinc oxide (IZO), or tin oxide, but other metal oxides such as Aluminum or indium doped tin oxide, magnesium-indium oxide, or nickel-tungsten oxide are also useful.
  • metal nitrides such as gallium nitride, metal selenides such as zinc selenide, or metal sulfides such as zinc sulfide can be used as the anode.
  • the anode can be modified with plasma deposited fluorocarbon.
  • the transmission properties of the anode are not critical and any conductive material that is transparent, opaque or reflective can be used.
  • conductors for this application include gold, iridium, molybdenum, palladium and platinum.
  • a hole injection layer can be provided between the anode and the hole transport layer.
  • the hole injection material can serve to improve the film forming properties of the subsequent organic layer and to facilitate injection of holes into the hole transport layer.
  • materials suitable for use in the hole injection layer include porphyrin compounds, plasma deposited fluorocarbon polymers, and amines having aromatic rings such as biphenyl groups and carbazole groups, such as m-MTDATA (4,4 ′ , 4 ′′ -tris [(3-methylphenyl) phenylamino] triphenylamine), 2T-NATA (4,4 ′, 4 ′′ -tris [(N-naphthalen-2-yl) -N-phenylamino ] Triphenylamine), triphenylamine, tolylamine, tolyldiphenylamine, N, N′-diphenyl-N, N′-bis (3-methylphenyl) -1,1′-biphenyl-4,4′-diamine, N,
  • hole transport material an aromatic tertiary amine having one or more amine groups can be used.
  • a polymeric hole transport material can be used.
  • PVK poly (N-vinylcarbazole)
  • PVK polythiophene
  • polypyrrole polyaniline
  • NPD N, N′-bis (naphthalen-1-yl) -N, N′-diphenyl-1,1′-biphenyl-4,4′-diamine
  • ⁇ -NPD N, N′-di
  • TPBi 1,3,5-tris (1-phenyl-1H-benzimidazol-2-yl) ) Benzene
  • TPD N, N′-bis (3-methylphenyl) -N, N′-diphenyl-1,1′-biphenyl-4,4′-diamine
  • a layer containing (HAT-CN) may be provided.
  • the light emitting layer of the organic electroluminescent element contains a phosphorescent material or a fluorescent material. In this case, light emission occurs as a result of recombination of electron-hole pairs in this region.
  • the emissive layer may consist of a single material including both small molecules and polymers, but more commonly consists of a host material doped with a guest compound, in which case the emission is mainly from the dopant. Occurs and can have any color.
  • Examples of the host material for the light emitting layer include compounds having a biphenyl group, a fluorenyl group, a triphenylsilyl group, a carbazole group, a pyrenyl group, or an anthryl group.
  • DPVBi 4,4′-bis (2,2-diphenylvinyl) -1,1′-biphenyl
  • BCzVBi 4,4′-bis (9-ethyl-3-carbazovinylene) 1,1′-biphenyl
  • TBADN (2-tert-butyl-9,10-di (2-naphthyl) anthracene
  • ADN (9,10-di (2-naphthyl) anthracene
  • CBP 4,4′-bis (carbazole-9) -Yl) biphenyl
  • CDBP 4,4′-bis (carbazol-9-yl) -2,2′-dimethylbiphenyl
  • the host material in the light emitting layer may be an electron transport material as defined below, a hole transport material as defined above, or another material that supports hole-electron recombination, or a combination of these materials.
  • fluorescent dopants examples include anthracene, tetracene, xanthene, perylene, rubrene, coumarin, rhodamine and quinacridone, dicyanomethylenepyran compounds, thiopyran compounds, polymethine compounds, pyrylium or thiapyrylium compounds, fluorene derivatives, perifanthene derivatives, indeno Examples include perylene derivatives, bis (azinyl) amine boron compounds, bis (azinyl) methane compounds, and carbostyryl compounds.
  • An example of a useful phosphorescent dopant is an organometallic complex of a transition metal of iridium, platinum, palladium, or osmium.
  • dopants examples include Alq 3 (tris (8-hydroxyquinoline) aluminum)), DPAVBi (4,4′-bis [4- (di-para-tolylamino) styryl] biphenyl), perylene, Ir (PPy) 3 ( And tris (2-phenylpyridine) iridium (III), FlrPic (bis (3,5-difluoro-2- (2-pyridyl) phenyl- (2-carboxypyridyl) iridium (III)), and the like.
  • the thin film forming material used for forming the electron transport layer of the organic electroluminescence device of the present invention is the triazine compound (1) of the present invention.
  • the electron transporting layer may contain another electron transporting material, and examples of the electron transporting material include alkali metal complexes, alkaline earth metal complexes, and earth metal complexes. Desirable alkali metal complexes, alkaline earth metal complexes, and earth metal complexes include, for example, 8-hydroxyquinolinate lithium (Liq), bis (8-hydroxyquinolinato) zinc, and bis (8-hydroxyquinolinate).
  • a hole blocking layer may be provided between the light emitting layer and the electron transport layer for the purpose of improving carrier balance.
  • Preferred compounds for the hole blocking layer include BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), Bphen (4,7-diphenyl-1,10-phenanthroline), BAlq (bis (2 -Methyl-8-quinolinolato) -4- (phenylphenolate) aluminum), or bis (10-hydroxybenzo [h] quinolinato) beryllium).
  • an electron injection layer may be provided for the purpose of improving electron injection properties and improving device characteristics (for example, light emission efficiency, low voltage driving, or high durability).
  • Preferred compounds for the electron injection layer include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthraquinodimethane, or anthrone. Etc.
  • the cathode used in the present invention can be formed from almost any conductive material.
  • Desirable cathode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3 ) mixture, indium , Lithium / aluminum mixtures, rare earth metals and the like.
  • the light emission characteristics of the organic electroluminescence device were evaluated by applying a direct current to the fabricated device at room temperature and using a luminance meter of LUMINANCE METER (BM-9) (TOPCON).
  • the resulting compound A-155 had a Tg of 139 ° C.
  • the crude product obtained from the filtrate was further purified by recrystallization once (toluene), and further purified by column chromatography (chloroform: hexane) to give the desired 2- ⁇ [2- (3-chlorophenyl) -6 -Phenylpyridin-4-yl] phenyl-3-yl ⁇ -4,6-diphenyl-1,3,5-triazine was obtained as a white powder (yield 1.88 g, yield 38%).
  • Element Example 1 As the substrate, a glass substrate with an ITO transparent electrode on which a 2 mm wide indium-tin oxide (ITO) film (thickness 110 nm) was patterned in a stripe shape was used. The substrate was cleaned with isopropyl alcohol and then surface treated by ozone ultraviolet cleaning. Each layer was vacuum-deposited on the cleaned substrate by a vacuum deposition method, and an organic electroluminescence device having a light-emitting area of 4 mm 2 as shown in FIG. Each organic material was formed by a resistance heating method.
  • ITO indium-tin oxide
  • the glass substrate was introduced into a vacuum evaporation tank, and the pressure was reduced to 1.0 ⁇ 10 ⁇ 4 Pa.
  • a hole injection layer 2 a charge generation layer 3, a hole transport layer 4, a light-emitting layer 5, an electron transport layer 6, and a cathode layer are formed as an organic compound layer on the glass substrate with an ITO transparent electrode shown in FIG. 7 were laminated in this order, and all were formed by vacuum deposition.
  • the hole injection layer 2 65 nm of HIL purified by sublimation was formed at a rate of 0.15 nm / second.
  • sublimated and purified HAT was deposited to a thickness of 5 nm at a rate of 0.05 nm / second.
  • HTL was formed to a thickness of 10 nm at a rate of 0.15 nm / second.
  • EML-1 and EML-2 were deposited to a thickness of 25 nm at a ratio of 95: 5 (deposition rate of 0.18 nm / second).
  • Each film thickness was measured with a stylus type film thickness meter (DEKTAK).
  • this element was sealed in a nitrogen atmosphere glove box having an oxygen and moisture concentration of 1 ppm or less.
  • a glass sealing cap and the above-described film-forming substrate epoxy type ultraviolet curable resin manufactured by Nagase ChemteX Corporation were used.
  • Element Example 2 In Device Example 1, 2- ⁇ 4 ′-[4- (2-naphthyl) -6-phenylpyridin-2-yl] biphenyl-3-yl ⁇ synthesized in Example-2 instead of Compound A-2
  • An organic electroluminescent device was prepared and evaluated in the same manner as in Device Example 1 except that -4,6-diphenyl-1,3,5-triazine (Compound A-362) was used. The results are shown in Table 1.
  • element lifetime after measuring element lifetime (h), it represented with the relative value which set the element lifetime of the element reference example 1 to 100.
  • Example 3 2- ⁇ 4 ′-[6- (2-naphthyl) -4-phenylpyridin-2-yl] biphenyl-3-yl ⁇ synthesized in Example 3 instead of Compound A-2 in Device Example 1
  • An organic electroluminescent device was prepared and evaluated in the same manner as in Device Example 1 except that -4,6-diphenyl-1,3,5-triazine (Compound A-722) was used. The results are shown in Table 1.
  • element lifetime, after measuring element lifetime (h) it represented with the relative value which set the element lifetime of the element reference example 1 to 100.
  • Element Example 4 2- ⁇ 4 ′-[2- (1-naphthyl) -6-phenylpyridin-4-yl] biphenyl-3-yl ⁇ synthesized in Example-6 instead of Compound A-2 in Device Example 1
  • An organic electroluminescent device was prepared and evaluated in the same manner as in Device Example 1 except that -4,6-diphenyl-1,3,5-triazine (Compound A-4) was used. The results are shown in Table 1.
  • element lifetime after measuring element lifetime (h), it represented with the relative value which set the element lifetime of the element reference example 1 to 100.
  • Element Example 5 In Device Example 1, 2- ⁇ 4 ′-[4- (1-naphthyl) -6-phenylpyridin-2-yl] biphenyl-3-yl ⁇ synthesized in Example-7 instead of Compound A-2
  • An organic electroluminescent device was prepared and evaluated in the same manner as in Device Example 1 except that -4,6-diphenyl-1,3,5-triazine (Compound A-364) was used. The results are shown in Table 1.
  • element lifetime, after measuring element lifetime (h) it represented with the relative value which set the element lifetime of the element reference example 1 to 100.
  • Element Example 6 2- ⁇ 4 ′-[4- (1-Naphtyl) -6- (2-naphthyl) pyridin-2-yl] biphenyl- synthesized in Example-8 instead of Compound A-2 in Device Example 1
  • An organic electroluminescent device was prepared and evaluated in the same manner as in Device Example 1 except that 3-yl ⁇ -4,6-diphenyl-1,3,5-triazine (Compound A-365) was used. The results are shown in Table 1.
  • element lifetime, after measuring element lifetime (h) it represented with the relative value which set the element lifetime of the element reference example 1 to 100.
  • Element Example 7 4,6-Diphenyl-2- [4 ′-(4,6-diphenylpyridin-2-yl) -biphenyl synthesized in Example-9 instead of Compound A-2 in Element Example 1
  • An organic electroluminescent device was prepared and evaluated in the same manner as in Device Example 1 except that -3-yl] -1,3,5-triazine (Compound A-721) was used. The results are shown in Table 1.
  • element lifetime, after measuring element lifetime (h) it represented with the relative value which set the element lifetime of the element reference example 1 to 100.
  • Element Example 8 In Device Example 1, 2-( ⁇ 4- [3- (9-phenanthryl) phenyl] -6-phenylpyridin-2-yl ⁇ phenyl-3-synthesized in Example-18 instead of Compound A-2 Yl) -4,6-diphenyl-1,3,5-triazine (Compound A-1422) was used, and an organic electroluminescence device was prepared and evaluated in the same manner as in Device Example 1. The results are shown in Table 1. In addition, about element lifetime, after measuring element lifetime (h), it represented with the relative value which set the element lifetime of the element reference example 1 to 100.
  • Element Example 9 In Device Example 1, instead of compound A-2, 2-( ⁇ 2- [3- (9-phenanthryl) phenyl] -6-phenylpyridin-4-yl ⁇ phenyl-3-synthesized in Example-19 was used. Yl) -4,6-diphenyl-1,3,5-triazine (Compound A-1282) was used, and an organic electroluminescent device was prepared and evaluated in the same manner as in Device Example 1. The results are shown in Table 1. In addition, about element lifetime, after measuring element lifetime (h), it represented with the relative value which set the element lifetime of the element reference example 1 to 100.
  • Element Reference Example 1 In Device Example 1, instead of compound A-2, 2- [5- (9-phenanthryl) -4 ′-(2-pyrimidyl) biphenyl-3-yl] -4 described in JP2011-063584 A An organic electroluminescent device was prepared and evaluated in the same manner as in Device Example 1 except that, 6-diphenyl-1,3,5-triazine (ETL-2) was used. The results are shown in Table 1. In addition, about element lifetime, after measuring element lifetime (h), the element lifetime of this element reference example 1 was made into the reference value (100).
  • the triazine compound (1) of the present invention is excellent in heat resistance of film quality, an organic electroluminescent device having excellent long life and luminous efficiency can be provided by using the compound.
  • the triazine compound (1) of the present invention is used as an electron transport material for an organic electroluminescence device which is excellent in a low driving voltage. Furthermore, according to the present invention, it is possible to provide an organic electroluminescence device having excellent power consumption.
  • the triazine compound (1) of the present invention provides a material that has excellent sublimation purification operability due to good thermal stability during sublimation purification, and is low in impurities that cause element degradation of organic electroluminescent elements. Can do. Moreover, since the triazine compound (1) of the present invention is excellent in the stability of the deposited film, it is possible to provide an organic electroluminescence device having a long life.
  • the thin film comprising the triazine compound (1) of the present invention is useful as a material for an organic electroluminescence device because it has excellent electron transport ability, hole blocking ability, oxidation-reduction resistance, water resistance, oxygen resistance, electron injection characteristics, and the like. It is useful as an electron transport material, a hole blocking material, a light emitting host material, and the like. It is particularly useful when used as an electron transport material. Further, since the triazine compound (1) of the present invention is a wide band gap compound, it can be suitably used not only for conventional fluorescent device applications but also for phosphorescent devices.

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Abstract

　L'invention concerne un matériau de transport d'électrons présentant une excellente résistance à la chaleur, une longue durée de vie dans un élément électroluminescent organique, et d'excellentes propriétés d'attaque à basse tension ou une excellente efficience lumineuse. L'invention concerne aussi un matériau pour un élément électroluminescent organique, représenté par la formule générale (1). (Dans la formule générale (1), Ar1, Ar2, Ar3, R5, R6, R7, n, p, q, r, Z1, et Z2 ont les significations décrites dans la revendication 1).
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