WO2014104235A1 - Composé benzénique trisubstitué en positions 1, 2 et 4 et son procédé de production, et élément électroluminescent organique - Google Patents

Composé benzénique trisubstitué en positions 1, 2 et 4 et son procédé de production, et élément électroluminescent organique Download PDF

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WO2014104235A1
WO2014104235A1 PCT/JP2013/084972 JP2013084972W WO2014104235A1 WO 2014104235 A1 WO2014104235 A1 WO 2014104235A1 JP 2013084972 W JP2013084972 W JP 2013084972W WO 2014104235 A1 WO2014104235 A1 WO 2014104235A1
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華奈 藤田
信道 新井
桂甫 野村
尚志 飯田
田中　剛
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東ソー株式会社
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Definitions

  • the present invention relates to a 1,2,4-tris-substituted benzene compound, a method for producing the same, and a high-efficiency organic electroluminescent device using the same for at least one organic compound layer and having excellent light emission characteristics.
  • the organic electroluminescent element has a structure in which a light emitting layer containing a light emitting material is sandwiched between a hole transport layer and an electron transport layer, and an anode and a cathode are attached to the outside, and holes injected into the light emitting layer and It is a self-emitting element that utilizes a light emission phenomenon (fluorescence or phosphorescence) when excitons generated by electron recombination are deactivated. Since it is a self-luminous type, it is excellent in visibility, and since it is a completely solid element, it is easy to handle and manufacture. In addition, since it is a thin film type device, it is attracting attention from the viewpoints of space saving and portability, and is applied to displays, lighting, and the like. At present, the organic electroluminescence device has begun to be used for commercial purposes. However, further improvement in light emission efficiency, reduction in driving voltage, and longer life are required for energy saving.
  • Tris (8-quinolinolato) aluminum (III) (Alq) is an example of an electron transport material that has already been put to practical use.
  • the drive voltage is high. It was sought after.
  • Patent Document 1 discloses a host material for an electroluminescence element capable of obtaining an organic EL element having a long emission lifetime and excellent heat resistance, and an element using the same.
  • the host material is used as an electron transporting material, the device has been required to be improved because the driving voltage is increased.
  • An object of the present invention is to provide an electron transporting material which is excellent in the lifetime characteristics of the device and excellent in driving the device at a low voltage as compared with a conventionally known electron transporting material for an organic electroluminescence device.
  • an organic electroluminescent device using the 1,2,4-tris-substituted benzene compound shown in the present invention as an electron transport layer As compared with an organic electroluminescent device using a material for the electron transport layer, the driving voltage is significantly reduced and the lifetime is found, and the present invention has been completed.
  • the present invention relates to a 1,2,4-tris-substituted benzene compound represented by the following general formula (1) or (1) ′ (hereinafter referred to as “compound (1)” or “compound (1) ′”, respectively). And a manufacturing method thereof, and an organic electroluminescent element including the same as a constituent component.
  • Ar 1 represents an aromatic hydrocarbon group having 6 to 18 carbon atoms or a nitrogen-containing heteroaromatic group having 3 to 17 carbon atoms (these groups are alkyl groups having 1 to 8 carbon atoms, alkoxy groups, alkoxyalkyl groups, An ester group or an ester alkyl group, or an optionally substituted fluorine atom).
  • Ar 2 in formula (1) is a monovalent nitrogen-containing heteroaromatic group having 3 to 17 carbon atoms (an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group, or fluorine).
  • a divalent nitrogen-containing heteroaromatic group having 3 to 17 carbon atoms (an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, An ester group or an ester alkyl group, or an optionally substituted fluorine atom).
  • Ar 3 may be substituted with a nitrogen-containing heteroaromatic group having 3 to 17 carbon atoms (an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group, or a fluorine atom).
  • a substituent represented by —Ar 4 —Ar 5 Or a substituent represented by —Ar 4 —Ar 5 .
  • Ar 4 is a nitrogen-containing heteroarylene group having 3 to 17 carbon atoms (which may be substituted with an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group, or a fluorine atom).
  • Ar 5 is an aromatic hydrocarbon group having 6 to 18 carbon atoms, pyridyl group, pyrimidyl group, or pyrazyl group (these groups are alkyl groups having 1 to 8 carbon atoms, alkoxy groups, alkoxyalkyl groups, ester groups or esters). An alkyl group or a fluorine atom which may be substituted).
  • Ar 1 , Ar 2 , and Ar 3 is a pyridyl group, a pyrimidyl group, or a condensed ring group having 6 to 17 carbon atoms including a pyridine skeleton or a pyrimidine skeleton (these groups have a carbon number of 1 To 8 alkyl groups, alkoxy groups, alkoxyalkyl groups, ester groups or ester alkyl groups, or a fluorine atom, which may be substituted.
  • R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom or a substituent having 1 to 4 carbon atoms, and R 1 and R 2 , R 3 and R 4 , or R 1 and R 2 and R Both 3 and R 4 may be linked together to form an alicyclic or aromatic ring.
  • m represents 0 or 1.
  • n represents 0, 1, or 2.
  • Y 1 represents a divalent substituent represented by the following general formula (A)
  • Y 2 is a divalent substituent represented by the following general formula (A) in Formula (1), independently of Y 1.
  • a monovalent substituent represented by the following general formula (A) ′ is represented.
  • X 1 , X 2 and X 3 each independently represent CH or a nitrogen atom, and at least one is CH.
  • R 5 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group, or an ester alkyl group, a hydrogen atom, a fluorine atom, or a counter electron.
  • the total number of pyridyl groups and pyridylene groups, the total number of pyrimidyl groups and pyrimidylene groups, and the total number of pyrazyl groups and pyrazylene groups in the structure are each independently 0, 1 2, or 3.
  • each hydrogen atom in the formula may independently be a deuterium atom.
  • the compound (1) or (1) ′ of the present invention Since the compound (1) or (1) ′ of the present invention has good charge injection and transport properties, it is useful as an electron transport material of a fluorescent or phosphorescent organic electroluminescence device, and particularly used as an electron transport material. be able to.
  • the organic electroluminescent device having an electron transport layer containing the compound (1) or (1) ′ of the present invention has a significantly lower driving voltage and a higher driving voltage than an organic electroluminescent device using a general-purpose electron transport material. Efficiency and long life.
  • the band gap of the compound (1) or (1) ′ of the present invention is 3.2 eV or more, and the three primary colors constituting the panel (red: 1.9 eV, green: 2.4 eV, blue: 2.8 eV)
  • This material has a wide band gap sufficient to confine the energy of each color. Therefore, it can be applied to various elements such as a single color display element, a three primary color display element, and a white element for illumination use. Since the compound (1) of the present invention has a high triplet energy, it can be sufficiently applied to phosphorescence. Furthermore, since the solubility can be controlled by changing the substituent, it can be applied not only to a vapor deposition element but also to a coating element.
  • FIG. 3 is a cross-sectional view of an organic electroluminescent element produced in Test Example-1.
  • an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group is not particularly limited, and examples thereof include a methyl group (-Me), an ethyl group (- Et), n-propyl group (n-Pr), i-propyl group (i-Pr), n-butyl group (n-Bu), t-butyl group (t-Bu), pentyl group, hexyl group (- Hex), heptyl group, octyl group (above, alkyl group having 1 to 8 carbon atoms), methoxy group, ethoxy group, n-propyloxy group, i-propyloxy group, n-butyloxy group, t-butyloxy group, pentyl Oxy group, hexyloxy group, heptyloxy group, octyloxy group (above, alky
  • the aromatic hydrocarbon group having 6 to 18 carbon atoms is not particularly limited, and examples thereof include a phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2,3 -Dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 2-ethylphenyl group 3-ethylphenyl group, 4-ethylphenyl group, 2-ethyl-3-methylphenyl group, 2-ethyl-4-methylphenyl group, 2-ethyl-5- Tylphenyl group,
  • phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 1-naphthyl group, 2-naphthyl group, 2-phenanthrenyl are preferable in terms of performance as an organic electroluminescent element material.
  • Group, 9-phenanthrenyl group, 1-anthracenyl group, or 9-anthracenyl group is preferable, and phenyl group, 2-methylphenyl group, 3-methylphenyl group, or 4-methylphenyl group is more preferable.
  • the monovalent nitrogen-containing heteroaromatic group having 3 to 17 carbon atoms which may be used is not particularly limited, and examples thereof include 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 3- Methylpyridin-2-yl group, 4-methylpyridin-2-yl group, 5-methylpyridin-2-yl group, 6-methylpyridin-2-yl group, 2-methylpyridin-3-yl group, 4- Methylpyridin-3-yl group, 5-methylpyridin-3-yl group, 6-methylpyridin-3-yl group, 2-methylpyridin-4-yl group, 3-methylpyridin-4-yl group, 3, 4 Dimethylpyridin-2-yl group,
  • the divalent nitrogen-containing heteroaromatic group of 3 to 17 is not particularly limited.
  • pyridinediyl group methylpyridinediyl group, methoxypyridinediyl group, dimethylpyridinediyl group, ethylpyridinediyl group, Ethoxypyridinediyl group, propylpyridinediyl group, propoxypyridinediyl group, butylpyridinediyl group, butoxypyridinediyl group, methoxymethylpyridinediyl group, fluoropyridinediyl group, difluoropyridinediyl group, pyrimidinediyl group, methylpyrimidinediyl group, Methoxypyrimidine Yl, dimethylpyrimidinediyl, ethylpyrimidinediyl, ethoxypyrimidinediyl, propylpyrimidinediyl, propoxypyrimidinediyl, pentylpyrimidinediyl, pentoxypyrimidinediyl, pentoxypyr
  • Ar 1 and Ar 2 are each independently a pyridyl group, a pyrimidyl group, or a condensed ring group having 6 to 17 carbon atoms including a pyridine skeleton or a pyrimidine skeleton in terms of good performance as an organic electroluminescent element material ( These groups are monovalent or divalent, and may be substituted with an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group, or a fluorine atom).
  • a pyridyl group, a pyrimidyl group, or a condensed ring group having 6 to 9 carbon atoms including a pyridine skeleton or a pyrimidine skeleton (these groups are monovalent or divalent and have 1 to 8 carbon atoms).
  • Each of which is independently a pyridyl group, a pyrimidyl group, or a condensed ring group having 6 to 9 carbon atoms containing a pyridine skeleton (these groups are monovalent or divalent, More preferably, it may be substituted with an alkyl group, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group, or a fluorine atom.
  • a condensed ring group having 6 to 17 carbon atoms containing the pyridine skeleton or pyrimidine skeleton (these groups are an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group, or a fluorine atom.
  • these groups are an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group, or a fluorine atom.
  • Is not particularly limited, and examples thereof include quinolyl group, isoquinolyl group, naphthyridyl group, ⁇ -carbolyl group, phenanthridyl group, acridyl group, phenanthroyl group, and benzo [b].
  • a naphthylidyl group, a benzo [c] naphthylidyl group or the like may be substituted with an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group, or a fluorine atom.
  • the present invention is not limited to these examples.
  • quinolyl group, isoquinolyl group, ⁇ -carbolyl group, acridyl group, phenanthridyl group, or phenanthroyl group these groups are alkyl groups having 1 to 8 carbon atoms because of their good performance as organic electroluminescent device materials.
  • a bivalent condensed ring group having 6 to 17 carbon atoms containing the pyridine skeleton or pyrimidine skeleton (these groups are an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group; Or may be substituted with a fluorine atom), but is not particularly limited, for example, quinoline diyl group, isoquinoline diyl group, naphthyridine diyl group, ⁇ -carboline diyl group, phenanthridine diyl group, acridine diyl group Phenanthrolinediyl group, benzo [b] naphthyridinediyl group, benzo [c] naphthyridinediyl group, etc.
  • quinoline diyl group or an isoquinoline diyl group (these groups are alkyl groups having 1 to 8 carbon atoms, alkoxy groups, alkoxyalkyl groups, ester groups or ester alkyl groups in terms of good performance as organic electroluminescent element materials.
  • an optionally substituted with a fluorine atom and more preferably a quinolinediyl group or an isoquinolinediyl group (these groups may be substituted with a methyl group or a fluorine atom).
  • a condensed ring group having 6 to 9 carbon atoms containing the pyridine skeleton or pyrimidine skeleton (these groups are an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group, or a fluorine atom; Is not particularly limited, and examples thereof include a quinolyl group, an isoquinolyl group, or a naphthyridyl group (these groups include an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxy group).
  • an alkyl group, an ester group or an ester alkyl group, which may be substituted with a fluorine atom but the present invention is not limited thereto.
  • a quinolyl group or an isoquinolyl group (these groups are alkyl groups having 1 to 8 carbon atoms, alkoxy groups, alkoxyalkyl groups, ester groups or ester alkyl groups; Or may be substituted with a fluorine atom), and more preferably a quinolyl group or an isoquinolyl group (these groups may be substituted with a methyl group or a fluorine atom).
  • a divalent condensed ring group having 6 to 9 carbon atoms containing the pyridine skeleton or pyrimidine skeleton (these groups are an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group;
  • the group may be substituted with a fluorine atom, but is not particularly limited.
  • a quinoline diyl group, an isoquinoline diyl group, or a naphthyridine diyl group these groups are alkyl groups having 1 to 8 carbon atoms).
  • An alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group, or a fluorine atom may be substituted), but the present invention is not limited thereto.
  • a quinoline diyl group or an isoquinoline diyl group (these groups are alkyl groups having 1 to 8 carbon atoms, alkoxy groups, alkoxyalkyl groups, ester groups or ester alkyls) because of their good performance as organic electroluminescent device materials.
  • a quinoline diyl group or an isoquinoline diyl group (these groups may be substituted with a methyl group or a fluorine atom), more preferably.
  • Ar 1 and Ar 2 are each independently a pyrimidyl group, a pyridyl group, a quinolyl group, or an isoquinolyl group (these groups are monovalent or divalent, each independently having 1 to 8 carbon atoms).
  • an alkyl group, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group, or a fluorine atom each independently, a pyrimidyl group, a pyridyl group, a quinolyl group, Or an isoquinolyl group (these groups are monovalent or divalent and may be substituted with a methyl group or a fluorine atom), and each independently represents a 2-pyrimidyl group, 4-methyl Pyrimidin-2-yl group, 4,6-dimethylpyrimidin-2-yl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 6- Tylpyridin-2-yl group, 5-methylpyridin-2-yl group, 6-fluoropyridin-2-yl group, 5-fluoropyridin-2-yl group, 1-isoquinolyl group, or 2-quinolyl group (above, Monovalent), 2,5-pyrimid
  • Ar 1 and Ar 2 are preferably the same substituent as each other regardless of the difference between monovalent and divalent in terms of excellent production efficiency.
  • Ar 3 represents a nitrogen-containing heteroaromatic group having 3 to 17 carbon atoms (an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group, or an ester alkyl group). Or a substituent represented by —Ar 4 —Ar 5 (which may be substituted with a group or a fluorine atom).
  • Ar 4 represents a nitrogen-containing heteroarylene group having 3 to 17 carbon atoms (which may be substituted with an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group, or a fluorine atom).
  • Ar 5 represents an aromatic hydrocarbon group having 6 to 18 carbon atoms, a pyridyl group, a pyrimidyl group, or a pyrazyl group (an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group, Or may be substituted with a fluorine atom).
  • a nitrogen-containing heteroaromatic group having 3 to 17 carbon atoms in Ar 3 (which may be substituted with an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group, or a fluorine atom)
  • a nitrogen-containing heteroaromatic group having 3 to 17 carbon atoms exemplified for Ar 1 and Ar 2 (an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, Examples thereof include the same substituent groups as those of an ester group or an ester alkyl group, which may be substituted with a fluorine atom.
  • Ar 3 are points performance as good as the organic electroluminescence element material, is Ar 3, alkyl group, alkoxy group, nitrogen-containing heteroaromatic group (from 1 to 8 carbon atoms of a carbon number of 4 11, an alkoxyalkyl group , An ester group or an ester alkyl group, or a substituent represented by —Ar 4 —Ar 5 , and Ar 4 is a nitrogen-containing heteroarylene group having 4 to 12 carbon atoms
  • Ar 5 is an aromatic carbon atom having 6 to 18 carbon atoms (which may be substituted with an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group, or a fluorine atom).
  • a hydrogen group, a pyridyl group, a pyrimidyl group, or a pyrazyl group are each independently an alkyl group, alkoxy group, A alkoxyalkyl group, an ester group or an ester alkyl group, or a fluorine atom which may be substituted).
  • a nitrogen-containing heteroaromatic group having 4 to 11 carbon atoms represented by Ar 3 (substituted with an alkyl group, alkoxy group, alkoxyalkyl group, ester group or ester alkyl group having 1 to 8 carbon atoms, or a fluorine atom) May be, for example, pyridyl group, pyrimidyl group, pyrazyl group, quinolyl group, isoquinolyl group, naphthyridyl group, carbolyl group, benzothiazolyl group (these groups have 1 to 8 carbon atoms).
  • an alkyl group an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group, or a fluorine atom which may be substituted.
  • a nitrogen-containing heteroarylene group having 3 to 17 carbon atoms represented by Ar 4 which may be substituted with a C 1 to C 8 alkyl group, alkoxy group, alkoxyalkyl group, ester group or ester alkyl group, or a fluorine atom
  • Ar 4 which may be substituted with a C 1 to C 8 alkyl group, alkoxy group, alkoxyalkyl group, ester group or ester alkyl group, or a fluorine atom
  • a nitrogen-containing heteroaromatic group having 3 to 17 carbon atoms exemplified for Ar 1 and Ar 2 (an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group) Group, ester group or ester alkyl group, which may be substituted with a fluorine atom) eg pyrimidinediyl group, pyridinediyl group, quinolinediyl group, isoquinolinediyl group, nap
  • a nitrogen-containing heteroarylene group having 4 to 12 carbon atoms represented by Ar 4 (which may be substituted with an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group, or a fluorine atom) Is not particularly limited.
  • Groups, indolediyl groups, benzimidazolediyl groups, pyrrolopyridinediyl groups (these groups are substituted with alkyl groups having 1 to 8 carbon atoms, alkoxy groups, alkoxyalkyl groups, ester groups or ester alkyl groups, or fluorine atoms). May be) And the like.
  • a pyridinediyl group a pyrimidinediyl group, a benzimidazolediyl group, or a carbazolediyl group (these groups are an alkyl group having 1 to 8 carbon atoms, an alkoxy group in view of good performance as an organic electroluminescent element material.
  • An aromatic hydrocarbon group having 6 to 18 carbon atoms represented by Ar 5 (which may be substituted with an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group, or a fluorine atom)
  • Ar 1 an aromatic hydrocarbon group having 6 to 18 carbon atoms exemplified by Ar 1 (an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group)
  • an ester alkyl group, or the same substituent as that optionally substituted with a fluorine atom can be exemplified.
  • Ar 5 is a phenyl group optionally substituted with an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group, or a fluorine atom in terms of good performance as an organic electroluminescent element material. It is preferably a group, and more preferably a phenyl group.
  • Ar 3 is 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 6-methylpyridin-2-yl group, 5-methylpyridine- 2-yl group, 6-fluoropyridin-2-yl group, 5-fluoropyridin-2-yl group, 5-phenylpyridin-2-yl group, 6-phenylpyridin-3-yl group, 2-pyrimidyl group, 5-phenylpyrimidin-2-yl group, 3- (2-pyridyl) -9H-carbazol-9-yl group, 2-phenyl-1H-benzimidazol-1-yl group, 1-phenyl-1H-benzimidazole- A 2-yl group, a 2-benzothiazolyl group, a 1-isoquinolyl group, a 2-quinolyl group, or a ⁇ -carbolin-9-yl group is preferable.
  • At least one of Ar 1 , Ar 2 , and Ar 3 has a pyridyl group, a pyrimidyl group, a pyridine skeleton or a pyrimidine skeleton, and has 6 to 17 carbon atoms.
  • a condensed ring group (these groups may be substituted with an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group, or a fluorine atom);
  • a condensed ring group having 6 to 17 carbon atoms containing the pyridine skeleton or pyrimidine skeleton (these groups are an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group, or a fluorine atom.
  • At least one of Ar 1 , Ar 2 , and Ar 3 is a pyridyl group, a pyrimidyl group, a quinolyl group, an isoquinolyl group, a naphthyridyl group, a quinazolinyl group, and a carbolinyl group in terms of good performance as an organic electroluminescent element material.
  • a phenanthridinyl group, an acridinyl group, or a phenanthrolinyl group (these groups are substituted with an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group, or a fluorine atom)
  • the pyridyl group, pyrimidyl group, quinolyl group, isoquinolyl group, naphthyridyl group, quinazolinyl group, or carbolinyl group (these groups are substituted with a methyl group, a methoxy group, or a fluorine atom). More preferably).
  • R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom or a substituent having 1 to 4 carbon atoms, and R 1 , R 2 and R 3 And R 4 , or R 1 and R 2 and R 3 and R 4 may be linked to each other to form an alicyclic ring or an aromatic ring.
  • examples of the alicyclic ring include a cyclopentane ring and a cyclohexane ring
  • examples of the aromatic ring include, but are not limited to, a benzene ring.
  • Examples of the substituent having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a tert-butyl group, and an alkenyl group having 2 to 4 carbon atoms (for example, a vinyl group). ) And the like.
  • a vinyl group or a hydrogen atom, which are connected to each other to form an aromatic ring, is preferable in terms of good performance as an organic electroluminescent element material.
  • R 1 , R 2 , R 3 and R 4 are 1) all hydrogen atoms, 2) both R 1 and R 2 are alkenyl groups having 2 to 4 carbon atoms and are bonded to each other to form an aromatic ring Or 3) all of R 1 , R 2 , R 3 and R 4 are alkenyl groups having 2 to 4 carbon atoms, and R 1 and R 2 , and R 3 and R 4 are linked to each other It preferably forms an aromatic ring, 1) all are hydrogen atoms, 2) both R 1 and R 2 are vinyl groups and are bonded to each other to form a benzene ring, or 3) R More preferably, 1 , R 2 , R 3 and R 4 are all vinyl groups, and R 1 and R 2 , and R 3 and R 4 are connected to each other to form a benzene ring.
  • Y 1 represents a divalent substituent represented by the following General Formula (A)
  • Y 2 is the following in Formula (1) independently of Y 1.
  • the divalent substituent represented by the general formula (A) is represented.
  • the monovalent substituent represented by the following general formula (A) ′ is represented.
  • X 1 , X 2 and X 3 each independently represent CH or a nitrogen atom, and at least one is CH.
  • R 5 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group, or an ester alkyl group, a hydrogen atom, a fluorine atom, or a counter electron.
  • X 1 to X 3 are all CH, or X 1 is a nitrogen atom in terms of good performance as an organic electroluminescent device material, and X 2 and X 3 Is preferably CH.
  • a 1,4-phenylene group, a 2,5-pyridylene group, or a 2,5-pyrimidylene group are preferably each independently an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group, an ester alkyl group, or a fluorine atom.
  • a 1,4-phenylene group, a 2,5-pyridylene group, or a 2,5-pyrimidylene group (these groups may have a methyl group or a fluorine atom) are more preferable.
  • the monovalent Y 2 described in the general formula (1) ′ is a phenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, or 2- A pyrimidyl group (these groups may each independently have an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group, an ester alkyl group, or a fluorine atom); A phenyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, or a 2-pyrimidyl group (these groups may have a methyl group or a fluorine atom) are more preferable.
  • m represents 0 or 1. Note that m is preferably 1 in terms of good performance as an organic electroluminescent element material.
  • n is preferably 0 or 1 in terms of good performance as an organic electroluminescent element material.
  • the total number of pyridyl groups and pyridylene groups, the total number of pyrimidyl groups and pyrimidylene groups, and the total number of pyrazyl groups and pyrazilene groups are based on the presence or absence of the substituent of each group Regardless, each is independently limited to 0, 1, 2, or 3 (see Test Example-17 and Reference Example-3).
  • each hydrogen atom in the general formula (1) or (1) ′ may be independently a deuterium atom.
  • the compound (1) or (1) ′ of the present invention has the following reaction formula
  • Ar 1 represents an aromatic hydrocarbon group having 6 to 18 carbon atoms or a nitrogen-containing heteroaromatic group having 3 to 17 carbon atoms (these groups are alkyl groups having 1 to 8 carbon atoms, alkoxy groups, alkoxyalkyl groups, An ester group or an ester alkyl group, or an optionally substituted fluorine atom).
  • Ar 2 may be substituted with a nitrogen-containing heteroaromatic group having 3 to 17 carbon atoms (an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group, or a fluorine atom).
  • Ar 3 may be substituted with a nitrogen-containing heteroaromatic group having 3 to 17 carbon atoms (an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group, or a fluorine atom).
  • a substituent represented by —Ar 4 —Ar 5 Or a substituent represented by —Ar 4 —Ar 5 .
  • Ar 4 is a nitrogen-containing heteroarylene group having 3 to 17 carbon atoms (which may be substituted with an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group, or a fluorine atom).
  • Ar 5 is an aromatic hydrocarbon group having 6 to 18 carbon atoms, pyridyl group, pyrimidyl group, or pyrazyl group (these groups are alkyl groups having 1 to 8 carbon atoms, alkoxy groups, alkoxyalkyl groups, ester groups or esters). An alkyl group or a fluorine atom which may be substituted).
  • Ar 1 , Ar 2 , and Ar 3 is a pyridyl group, a pyrimidyl group, or a condensed ring group having 6 to 17 carbon atoms including a pyridine skeleton or a pyrimidine skeleton (these groups have a carbon number of 1 To 8 alkyl groups, alkoxy groups, alkoxyalkyl groups, ester groups or ester alkyl groups, or a fluorine atom, which may be substituted.
  • R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom or a substituent having 1 to 4 carbon atoms, and R 1 and R 2 , R 3 and R 4 , or R 1 and R 2 and R Both 3 and R 4 may be linked together to form an alicyclic or aromatic ring.
  • m represents 0 or 1.
  • n represents 0, 1, or 2.
  • Y 1 represents a divalent substituent represented by the following general formula (A)
  • Y 2 is a divalent substituent represented by the following general formula (A) in Formula (1), independently of Y 1.
  • a monovalent substituent represented by the following general formula (A) ′ is represented.
  • X 1 , X 2 and X 3 each independently represent CH or a nitrogen atom, and at least one is CH.
  • R 5 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group, or an ester alkyl group, a hydrogen atom, a fluorine atom, or a counter electron.
  • the total number of pyridyl groups and pyridylene groups, the total number of pyrimidyl groups and pyrimidylene groups, and the total number of pyrazyl groups and pyrazylene groups in the structure are each independently 0, 1 2, or 3.
  • each hydrogen atom in the formula may independently be a deuterium atom.
  • Z 1 , Z 2 and Z 3 each independently represent a leaving group.
  • M 1 , M 2 and M 3 each independently represent a metal group, a boronic acid group, or a boronic ester group. ) It can be manufactured by the method shown in
  • the compound represented by the general formula (2) is referred to as compound (2).
  • the compound (3), the compound (4), the compound (4) ′ and the compound (5) are produced using, for example, the methods disclosed in JP-A-2008-280330 (0061) to (0076). be able to.
  • Examples of the compound (3) include the following (A1) to (A178), but the present invention is not limited to these.
  • M 1 represents a metal group, a boronic acid group, or a boronic acid ester group.
  • Examples of the compound (4) include the following (B1) to (B84), but the present invention is not limited to these.
  • M 2 represents a metal group, a boronic acid group, or a boronic acid ester group.
  • Examples of the compound (4) ′ include the following (B85) to (B118), but the present invention is not limited to these.
  • M 2 represents a metal group, a boronic acid group, or a boronic acid ester group.
  • Examples of the compound (5) include compounds in which M 2 described in (B1) to (B84) is M 3 and the following (C1) to (C105), but the present invention is limited to these. It is not a thing.
  • M 3 represents a metal group, a boronic acid group, or a boronic acid ester group.
  • Step 1 is the step of reacting compound (2) with compound (3), compound (4) or compound (4) ′, and compound (5) in the presence of a metal catalyst or in the presence of a metal catalyst and a base.
  • This is a method for obtaining the compound (1) or (1) ′ of the present invention, and applies general reaction conditions for coupling reactions such as Suzuki-Miyaura reaction, Negishi reaction, Tamao-Kumada reaction, Stille reaction, etc. By doing so, the target product can be obtained in good yield.
  • the reaction sequence when reacting the compound (3), the compound (4) or the compound (4) ′, and the compound (5) is random, and the intermediates may be taken out by sequentially reacting or reacting simultaneously. Also good.
  • M 1 , M 2 and M 3 in compound (3), compound (4), compound (4) ′ and compound (5) are ZnA 1 , MgA 2 , Sn (A 3 ) 3 , B (OA 4 ) 2 etc. are mentioned.
  • a 1 and A 2 each independently represent a chlorine atom, a bromine atom or an iodine atom
  • a 3 represents an alkyl group having 1 to 4 carbon atoms or a phenyl group
  • a 4 represents a hydrogen atom or carbon number 1 4 represents an alkyl group or a phenyl group
  • two A 4 of B (OA 4 ) 2 may be the same or different.
  • the two A 4 can also form a ring containing an oxygen atom and a boron atom together.
  • B (OA 4 ) 2 in the case where two A 4 are united to form a ring containing an oxygen atom and a boron atom include groups represented by the following (D1) to (D6): The group represented by (D2) is preferable because it can be exemplified and the yield is good.
  • Examples of the leaving group represented by Z 1 , Z 2 and Z 3 in the compound (2) include a chlorine group, a bromine group, an iodine group, a trifluoromethylsulfonyloxy (OTf) group, a methanesulfonyloxy group, and a chloromethanesulfonyl. Examples thereof include an oxy group and a p-toluenesulfonyloxy group. Examples of the compound (2) include the following (E1) to (E5), but the present invention is not limited to these.
  • Examples of the metal catalyst that can be used in “Step 1” include a palladium catalyst and a nickel catalyst.
  • Examples of the palladium catalyst that can be used in “Step 1” include salts of palladium chloride, palladium acetate, palladium trifluoroacetate, palladium nitrate, and the like.
  • a palladium complex having a tertiary phosphine as a ligand is preferable in terms of a good reaction yield.
  • a palladium complex having tertiary phosphine as a ligand can also be prepared in a reaction system by adding tertiary phosphine to a palladium salt or complex compound.
  • the tertiary phosphine that can be used at this time is triphenylphosphine, trimethylphosphine, tributylphosphine, tri (tert-butyl) phosphine, tricyclohexylphosphine, tert-butyldiphenylphosphine, 9,9-dimethyl-4,5.
  • 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 in terms of good reaction yield.
  • the nickel catalyst that can be used in “Step 1” includes [1,1′-bis (diphenylphosphino) ferrocene] nickel (II) dichloride, [1,2-bis (diphenylphosphino) ethane] nickel ( II) Dichloride, [1,3-bis (diphenylphosphino) propane] nickel (II) dichloride, [1,1′-bis (diphenylphosphino) propane] nickel (II) dichloride, 1,2-bis (diphenyl) Phosphino) ethane] nickel (II) dichloride, [1,3-bis (diphenylphosphino) propane] nickel (II) dichloride, and the like.
  • Examples of the base that can be used in “Step 1” include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, lithium carbonate, cesium carbonate, tripotassium phosphate, sodium phosphate, sodium fluoride, potassium fluoride, Cesium fluoride and the like can be exemplified, and tripotassium phosphate is desirable in terms of a good yield.
  • the molar ratio of the base to the compound (3), the compound (4) and the compound (5) is preferably 1: 2 to 10: 1, and more preferably 1: 1 to 3: 1 in terms of a good yield.
  • Examples of the solvent that can be used in “Step 1” include water, dimethyl sulfoxide, dimethylformamide, tetrahydrofuran, dioxane, toluene, benzene, diethyl ether, ethanol, methanol, and xylene, and these may be used in appropriate combination. . It is desirable to use a mixed solvent of dioxane and water in terms of a good yield.
  • Step 1 can be performed at a temperature appropriately selected from 0 ° C. to 150 ° C., and is more preferably performed at 80 ° C. to 100 ° C. in terms of a good yield.
  • Compound (1) can be obtained by performing a normal treatment after completion of “Step 1”. If necessary, it may be purified by recrystallization, column chromatography or sublimation.
  • Ar 1 represents an aromatic hydrocarbon group having 6 to 18 carbon atoms or a nitrogen-containing heteroaromatic group having 3 to 17 carbon atoms (these groups are alkyl groups having 1 to 8 carbon atoms, alkoxy groups, alkoxyalkyl groups, An ester group or an ester alkyl group, or an optionally substituted fluorine atom).
  • Ar 2 may be substituted with a nitrogen-containing heteroaromatic group having 3 to 17 carbon atoms (an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group, or a fluorine atom).
  • Ar 3 may be substituted with a nitrogen-containing heteroaromatic group having 3 to 17 carbon atoms (an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group, or a fluorine atom).
  • a substituent represented by —Ar 4 —Ar 5 Or a substituent represented by —Ar 4 —Ar 5 .
  • Ar 4 is a nitrogen-containing heteroarylene group having 3 to 17 carbon atoms (which may be substituted with an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group or an ester alkyl group, or a fluorine atom).
  • Ar 5 is an aromatic hydrocarbon group having 6 to 18 carbon atoms, pyridyl group, pyrimidyl group, or pyrazyl group (these groups are alkyl groups having 1 to 8 carbon atoms, alkoxy groups, alkoxyalkyl groups, ester groups or esters). An alkyl group or a fluorine atom which may be substituted).
  • Ar 1 , Ar 2 , and Ar 3 is a pyridyl group, a pyrimidyl group, or a condensed ring group having 6 to 17 carbon atoms including a pyridine skeleton or a pyrimidine skeleton (these groups have a carbon number of 1 To 8 alkyl groups, alkoxy groups, alkoxyalkyl groups, ester groups or ester alkyl groups, or a fluorine atom, which may be substituted.
  • R 1 , R 2 , R 3 and R 4 each independently represent a hydrogen atom or a substituent having 1 to 4 carbon atoms, and R 1 and R 2 , R 3 and R 4 , or R 1 and R 2 and R Both 3 and R 4 may be linked together to form an alicyclic or aromatic ring.
  • m represents 0 or 1.
  • n represents 0, 1, or 2.
  • Y 1 represents a divalent substituent represented by the following general formula (A)
  • Y 2 is a divalent substituent represented by the following general formula (A) in Formula (1), independently of Y 1.
  • a monovalent substituent represented by the following general formula (A) ′ is represented.
  • X 1 , X 2 and X 3 each independently represent CH or a nitrogen atom, and at least one is CH.
  • R 5 each independently represents an alkyl group having 1 to 8 carbon atoms, an alkoxy group, an alkoxyalkyl group, an ester group, or an ester alkyl group, a hydrogen atom, a fluorine atom, or a counter electron.
  • the total number of pyridyl groups and pyridylene groups, the total number of pyrimidyl groups and pyrimidylene groups, and the total number of pyrazyl groups and pyrazylene groups in the structure are each independently 0, 1 2, or 3.
  • each hydrogen atom in the formula may independently be a deuterium atom.
  • Z 1 and Z 2 each independently represent a leaving group.
  • M 1 and M 2 each independently represent a metal group, a boronic acid group, or a boronic ester group.
  • W represents a substituent necessary for carrying out the heterocycle formation reaction. ) It can be manufactured by the method shown in
  • Step 2 can be performed in the same manner as “Step 1”, and the conditions thereof are the same as those of “Step 1”.
  • “Step 3” is a method of converting the site represented by W of compound (7) and compound (7) ′ to Ar 3 by a heterocycle formation reaction, and includes imidazole synthesis, indole synthesis, oxazole synthesis, and Erdman cyclization. Known methods such as reaction can be applied.
  • Examples of the substituent necessary for carrying out the heterocycle-forming reaction represented by W in compound (7) and compound (7) ′ include formyl group, amino group, ester group, carbonyl group, nitrile group and the like. Can be mentioned.
  • film formation by vacuum vapor deposition 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 evaporation method is reached by a commonly used diffusion pump, turbo molecular pump, cryopump, etc., considering the manufacturing tact time and manufacturing cost of organic electroluminescence device production. It is preferably about 1 ⁇ 10 ⁇ 2 to 1 ⁇ 10 ⁇ 5 Pa.
  • the deposition rate is preferably 0.005 to 1.0 nm / sec depending on the thickness of the film to be formed.
  • the compound (1) or (1) ′ of the present invention can be formed into a film by a spin coat method, an ink jet method, a cast method, a dip method or the like using a general-purpose apparatus.
  • 2′-formyl-4,4 ′′ -di (2-pyridyl) -1,1 ′: 1.98 g (4.80 mmol) of 4 ′, 1 ′′ -terphenyl, and N-phenyl-1,2- 1.33 g (7.20 mmol) of phenylenediamine was dissolved in a mixed solvent of 51 mL of toluene and 13 mL of acetic acid, and heated and stirred at 100 ° C. for 20 hours. After cooling to room temperature, 150 mL of pure water was added, followed by separation / extraction with chloroform, and the organic layer was separated and washed twice with pure water.
  • Test Example-1 Preparation and evaluation of the organic electroluminescent element were performed as follows.
  • a glass substrate with an ITO transparent electrode in which a 2 mm-wide indium-tin oxide (ITO) film was patterned in a stripe shape was used as the substrate.
  • 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.
  • the glass substrate was introduced into a vacuum evaporation tank, and the pressure was reduced to 1.0 ⁇ 10 ⁇ 4 Pa. Thereafter, a hole injection layer 2, a hole transport layer 3, a light emitting layer 4 and an electron transport layer 5 are sequentially formed as an organic compound layer on the glass substrate indicated by 1 in FIG. Filmed.
  • a hole injection layer 2 sublimation-purified phthalocyanine copper (II) was vacuum-deposited with a film thickness of 25 nm.
  • N, N′-di (1-naphthyl) -N, N′-diphenylbenzidine (NPD) was vacuum-deposited with a film thickness of 45 nm.
  • Each organic material was formed into a film by a resistance heating method, and the heated compound was vacuum-deposited at a film formation rate of 0.6 to 3.0 nm / second. Finally, a metal mask was disposed so as to be orthogonal to the ITO stripe, and the cathode layer 6 was formed.
  • the cathode layer 6 was made into a two-layer structure by vacuum deposition of lithium fluoride and aluminum with a thickness of 1.0 nm and 100 nm, respectively. Each film thickness was measured with a stylus type film thickness meter (DEKTAK). Furthermore, this element was sealed in a nitrogen atmosphere glove box having an oxygen and moisture concentration of 1 ppm or less. For the sealing, a glass sealing cap and the above-described film-forming substrate epoxy type ultraviolet curable resin (manufactured by Nagase ChemteX Corporation) were used.
  • a direct current was applied to the produced organic electroluminescence device, and the light emission characteristics were evaluated using a luminance meter of LUMINANCE METER (BM-9) manufactured by TOPCON.
  • V voltage
  • cd / m 2 luminance
  • cd / A current efficiency
  • lm / W power efficiency
  • the measured values of the fabricated element were 4.49 V, 2020 cd / m 2 , 10.1 cd / A, 7.07 lm / W.
  • Test Example-2 (Example) 2 ′-(2-benzothiazolyl) -4,4 ′′ -di (2-pyridyl) -1,1 ′: 4 ′ obtained in Experimental Example-5 instead of the electron transporting layer 5 in Test Example-1.
  • An organic electroluminescent device obtained by vacuum-depositing 1,1 ′′ -terphenyl was prepared and evaluated in the same manner as in Test Example-1.
  • the measured values of the fabricated elements were 4.98 V, 1428 cd / m 2 , 7.14 cd / A, and 4.50 lm / W, respectively.
  • Test Example 3 (Example) 4- (2-benzothiazolyl) -4 ′′-(2-pyridyl) -5 ′-[4- (2-pyridyl) obtained in Experimental Example-6 instead of the electron transport layer 5 of Test Example-1
  • An organic electroluminescent device in which phenyl] -1,1 ′: 2 ′, 1 ′′ -terphenyl was vacuum-deposited was prepared and evaluated in the same manner as in Test Example-1.
  • the measured values of the fabricated elements were 4.83 V, 1472 cd / m 2 , 7.36 cd / A, and 4.79 lm / W, respectively.
  • Test Example 4 (Example) 4- (2-Phenyl-1H-benzoimidazol-1-yl) -4 ′′-(2-pyridyl) -5 ′ obtained in Experimental Example-7 in place of the electron transport layer 5 of Test Example-1 An organic electroluminescent device obtained by vacuum-depositing — [4- (2-pyridyl) phenyl] -1,1 ′: 2 ′, 1 ′′ -terphenyl was prepared and evaluated in the same manner as in Test Example-1. The measured values of the fabricated elements were 4.65 V, 1944 cd / m 2 , 9.72 cd / A, and 6.57 lm / W, respectively.
  • Test Example-5 The 4- (1-phenyl-1H-benzoimidazol-2-yl) -4 ′′-(2-pyridyl) -5 ′ obtained in Experimental Example-8 was used in place of the electron transport layer 5 in Test Example-1.
  • the measured values of the fabricated elements were 5.42 V, 1824 cd / m 2 , 9.12 cd / A, and 5.29 lm / W, respectively. Further, the luminance 20% deterioration time during continuous lighting of this element was 35 hours.
  • Test Example-6 (Example) Instead of the electron transport layer 5 of Test Example-1, 4,4 ′′ -di (2-quinolyl) -4 ′-[4- (2-quinolyl) phenyl] -1, obtained in Experimental Example-16 An organic electroluminescent device obtained by vacuum-depositing 1 ′: 2 ′, 1 ′′ -terphenyl was prepared and evaluated in the same manner as in Test Example-1. The measured values of the fabricated elements were 5.84 V, 2020 cd / m 2 , 10.1 cd / A, and 5.43 lm / W, respectively.
  • Comparative Example-1 In place of the electron transport layer 5 in Test Example 1, an organic electroluminescent device in which Alq was vacuum-deposited was produced and evaluated in the same manner as in Test Example-1.
  • the measured values of the fabricated elements were 7.47 V, 1661 cd / m 2 , 8.31 cd / A, and 3.49 lm / W, respectively. Further, the luminance 20% deterioration time during continuous lighting of this element was 34 hours.
  • the measurement results of Test Examples 1 to 6 and Comparative Example 1 are summarized in the following table.
  • Test Example-7 (Example) 4- (2-Phenyl-1H-benzoimidazol-1-yl) -4 ′′-(1-isoquinolyl) -5 ′ obtained in Experimental Example-13 instead of the electron transport layer 5 in Test Example-1 -[4- (1-Isoquinolyl) phenyl] -1,1 ′: 2 ′, 1 ′′ -terphenyl is changed to the light-emitting layer 4 to produce 2-tert-butyl-9,10-di (3-biphenyl) ) Anthracene (formula below, see EML-1) and N, N′-diphenyl-N, N′-bis (4-biphenyl) pyrene-1,6-diamine (formula below, see EML-2) 95: 5 An organic electroluminescent device vacuum-deposited at a ratio of (% by mass) was produced and evaluated in the same manner as in Test Example-1.
  • the measured values of the fabricated elements were 5.87 V, 1244 cd / m 2 , 6.22 cd / A, and 3.33 lm / W, respectively. Further, the 30% luminance degradation time during continuous lighting of this element was 58 hours.
  • Test Example-8 (Example) The 4- (5-methylpyridin-2-yl) -4 ′′-(2-phenyl-1H-benzoimidazole-1-) obtained in Experimental Example-20 was used instead of the electron transporting layer 5 in Test Example-7.
  • Yl) -4 ′-[4- (5-methylpyridin-2-yl) phenyl] -1,1 ′: 2 ′, 1 ′′ -terphenyl was vacuum-deposited and an organic electroluminescent device was tested in Test Example 7 Were prepared and evaluated. The measured values of the fabricated elements were 4.72 V, 1407 cd / m 2 , 7.04 cd / A, and 4.68 lm / W, respectively.
  • Test Example-9 (Example) 4,4 ′ ′′-di (2-pyridyl) -2 ′-[4- (2-pyridyl) phenyl] -1 obtained in Experiment 21 instead of the electron transport layer 5 in Test Example-7 , 1 ′: 4 ′, 1 ′′: 4 ′′, 1 ′ ′′-Quaterphenyl was vacuum-deposited and an organic electroluminescent device was produced and evaluated in the same manner as in Test Example-7.
  • the measured values of the fabricated elements were 5.32 V, 1465 cd / m 2 , 7.33 cd / A, and 4.33 lm / W, respectively.
  • Test Example-10 (Example) 4 ′-[(2-Pyridyl) naphthalen-4-yl] -4,4 ′′ -di (2-pyridyl)-obtained in Experimental Example-22 instead of Electron Transport Layer 5 in Test Example-7
  • An organic electroluminescent device obtained by vacuum-depositing 1,1 ′: 2 ′, 1 ′′ -terphenyl was prepared and evaluated in the same manner as in Test Example-7.
  • the measured values of the fabricated elements were 6.24 V, 1379 cd / m 2 , 6.90 cd / A, and 3.47 lm / W, respectively.
  • Test Example-11 (Example) 2 ′-[5- (2-Phenyl-1H-benzimidazol-1-yl) pyridin-2-yl] -4,4 obtained in Experimental Example-23 instead of the electron transport layer 5 in Test Example-7
  • An organic electroluminescent device obtained by vacuum-depositing ′′-(2-pyridyl) -1,1 ′: 4 ′, 1 ′′ -terphenyl was prepared and evaluated in the same manner as in Test Example-7.
  • the measured values of the fabricated elements were 4.96 V, 1332 cd / m 2 , 6.66 cd / A, and 4.22 lm / W, respectively. Further, the 30% luminance degradation time when the device was continuously lit was 40 hours.
  • Test Example-7 An organic electroluminescent device obtained by vacuum deposition was prepared and evaluated in the same manner as in Test Example-7.
  • the measured values of the fabricated elements were 6.79 V, 1193 cd / m 2 , 5.97 cd / A, and 2.76 lm / W, respectively. Further, the 30% luminance degradation time during continuous lighting of this element was 50 hours.
  • the measurement results of Test Examples 7 to 11 and Reference Example 1 are summarized in the following table.
  • Test Example-12 (Example) 4- (2-pyridyl) -2 ′-[4- (2-pyridyl) phenyl] -1,1 ′: 4 ′ obtained in Experiment Example 2 instead of the electron transport layer 5 in Test Example 1 , 1 ′′: 4 ′′, 1 ′ ′′-quaterphenyl is changed to the light-emitting layer 4, and 2-tert-butyl-9,10-di (2-naphthyl) anthracene (TBADN) and 4,4
  • An organic electroluminescence device obtained by vacuum-depositing '-bis [4- (di-p-tolylamino) phenylethen-1-yl] biphenyl (DPAVBi) at a ratio of 93: 7 (mass%) was the same as in Test Example 1.
  • the measured values of the fabricated elements were 4.53 V, 2130 cd / m 2 , 10.65 cd / A, and 7.39 lm
  • Comparative Example-2 In place of the electron transport layer 5 in Test Example-12, an organic electroluminescent device in which Alq was vacuum-deposited was produced and evaluated in the same manner as in Test Example-12.
  • the measured values of the fabricated elements were 6.04 V, 1902 cd / m 2 , 9.51 cd / A, and 4.95 lm / W, respectively.
  • the measurement results of Test Example 12 and Comparative Example 2 are summarized in the following table.
  • Test Example-13 (Example) Instead of the electron transport layer 5 of Test Example-1, 4,4 ′′ -di (1-isoquinolyl) -4 ′-[4- (1-isoquinolyl) phenyl] -1, obtained in Experiment Example-11, An organic electroluminescent device obtained by vacuum-depositing 1 ′: 2 ′, 1 ′′ -terphenyl was prepared in the same manner as in Test Example 1, except that the substrate surface treatment method was changed from ozone ultraviolet cleaning to oxygen plasma cleaning. evaluated. The measured values of the fabricated elements were 5.70 V, 1779 cd / m 2 , 8.90 cd / A, and 4.90 lm / W, respectively.
  • Comparative Example-3 In place of the electron transport layer 5 of Test Example-13, an organic electroluminescent device in which Alq was vacuum-deposited was produced and evaluated in the same manner as Test Example-13.
  • the measured values of the fabricated elements were 6.20 V, 1957 cd / m 2 , 9.79 cd / A, and 4.96 lm / W, respectively.
  • the measurement results of Test Example 13 and Comparative Example 3 are summarized in the following table.
  • Test Example-14 (Example) Instead of the hole injection layer 2 of Test Example 1, the sublimated and purified HIL is changed to a thickness of 45 nm and changed to the hole transport layer 3, and HAT and HTL are changed to a thickness of 5 nm and 30 nm, respectively.
  • EML-1 and EML-2 (same as above) at a ratio of 958: 42 (mass%) with a film thickness of 20 nm
  • the electron transport layer 5 was used and synthesized in Experimental Example 27 of the present invention.
  • Test Example-15 (Example) 4- ( ⁇ -carbolin-9-yl) -4 ′′-(2-pyridyl) -5 ′-[4] synthesized in Experimental Example-25 of the present invention instead of the electron transport layer 5 in Test Example-14
  • An organic electroluminescent device in which — (2-pyridyl) phenyl] -1,1 ′: 2 ′, 1 ′′ -terphenyl was vacuum-deposited was prepared and measured in the same manner as in Test Example-14. The evaluation results of the fabricated devices are shown in the table below.
  • Test Example-16 (Example) Instead of the electron transport layer 5 in Test Example-14, 2 ′-[5- ( ⁇ -carbolin-9-yl) pyridin-2-yl] -4,4 ′ obtained in Experiment Example-26 of the present invention was used.
  • An organic electroluminescent device obtained by vacuum-depositing '-(2-pyridyl) -1,1': 4 ', 1''-terphenyl was prepared and measured in the same manner as in Test Example-14. The evaluation results of the fabricated devices are shown in the table below.
  • Test Example-17 The thickness of the hole injection layer 2 in Test Example-14 was changed to 65 nm, the thickness of the hole transport layer 3HTL was changed to 10 nm, and the light emitting layer 4 was changed to 954 for EML-1 and EML-2 (shown in Chemical Formula 53):
  • the thickness of the film was 25 nm at a ratio of 46 (mass%), and instead of the electron transport layer 5, 4,4 ′′ -di (2-pyridyl) -4 ′-[4- (2 -Pyridyl) phenyl] -1,1 ': 2', 1 ''-terphenyl was vacuum-deposited with a cathode layer 6Liq having a thickness of 0.5 nm to produce an organic electroluminescent device in the same manner as in Test Example-14 And measured.
  • the measured value evaluation results of the fabricated devices are shown in the table below. Further, the 20% luminance deterioration time during continuous lighting of this element was 105 hours.
  • the thin film comprising the compound (1) or (1) ′ of the present invention has high thin film stability, heat resistance, electron transport properties, hole blocking ability, redox resistance, water resistance, oxygen resistance, electron injection properties, etc. Therefore, it can be suitably used as an organic electroluminescent element material, particularly as an electron transporting material. Further, the compound (1) or (1) ′ of the present invention has a wide energy gap and triplet energy, and can be used in combination with a fluorescent or phosphorescent organic electroluminescent material. In addition, the compound (1) or (1) ′ of the present invention can be used for a light-emitting host layer and the like in addition to the electron transport layer because of its characteristics. Moreover, it can be used even if it mixes or laminates with another compound as an electron carrying layer.
  • this compound has high solubility, and can be used for coating elements in addition to vapor deposition. From these effects, these elements are expected to have significant effects such as suppression of battery consumption by reducing power consumption, improvement of product life by extending life, and reduction of burden on the drive circuit.
  • the entire contents of the specification, claims, drawings and abstract of Japanese Patent Application No. 2012-287908 filed on Dec. 28, 2012 are cited here as disclosure of the specification of the present invention. Incorporated.

Abstract

La présente invention concerne : un élément électroluminescent organique présentant une efficacité élevée, pouvant être excité à basse tension et ayant une longue durée de vie ; et un matériau, en particulier un matériau transporteur d'électrons, qui permet de produire l'élément électroluminescent organique. L'invention concerne ainsi un composé benzénique trisubstitué en positions 1, 2 et 4 représenté par la formule (1) ou (1)' ; et un élément électroluminescent organique produit au moyen du composé. Dans les formules, Ar1 représente un groupe hydrocarboné aromatique ayant de 6 à 18 atomes de carbone ou analogue, Ar2 représente un groupe hétéroaromatique azoté monovalent ou bivalent ayant de 3 à 17 atomes de carbone, et Ar3 représente un groupe hétéroaromatique azoté ayant de 3 à 17 atomes de carbone ou analogue, au moins un des Ar1, Ar2 et Ar3 représentant un groupe pyridyle ou analogue ; les R1, R2, R3 et R4 représentent indépendamment un atome d'hydrogène ou analogue ; m représente 0 ou 1 ; n représente 0, 1 ou 2 ; les Y1 et Y2 représentent indépendamment un groupe monovalent ou bivalent représenté par la formule (A) ou (A)' (dans laquelle les X1, X2 et X3 représentent indépendamment CH ou analogue et au moins un des X1, X2 et X3 représente CH) ; et les R5 représentent indépendamment un groupe alkyle ayant de 1 à 8 atomes de carbone ou analogue) (dans la structure, le nombre total de groupes pyridyle, pyridylène et analogues représente de 0 à 3 indépendamment de la présence ou de l'absence de substituants ; et dans les formules, chacun des atomes d'hydrogène peut être un atome de deutérium).
PCT/JP2013/084972 2012-12-28 2013-12-26 Composé benzénique trisubstitué en positions 1, 2 et 4 et son procédé de production, et élément électroluminescent organique WO2014104235A1 (fr)

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KR20230068995A (ko) * 2021-11-11 2023-05-18 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자
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