WO2018173882A1 - Composé d'azine cyclique, matériau pour élément électroluminescent organique, et matériau de transport d'électrons pour élément électroluminescent organique - Google Patents

Composé d'azine cyclique, matériau pour élément électroluminescent organique, et matériau de transport d'électrons pour élément électroluminescent organique Download PDF

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WO2018173882A1
WO2018173882A1 PCT/JP2018/009952 JP2018009952W WO2018173882A1 WO 2018173882 A1 WO2018173882 A1 WO 2018173882A1 JP 2018009952 W JP2018009952 W JP 2018009952W WO 2018173882 A1 WO2018173882 A1 WO 2018173882A1
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group
pyridyl
phenyl
carbon atoms
unsubstituted
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PCT/JP2018/009952
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Japanese (ja)
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服部一希
田中剛
野村桂甫
太田恵理子
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東ソー株式会社
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  • the present disclosure relates to a cyclic azine compound, a material for an organic electroluminescent element, and an electron transport material for an organic electroluminescent element.
  • An organic electroluminescent element has a basic 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 a light-emitting element that utilizes light emission (fluorescence or phosphorescence) when excitons generated by electron recombination are deactivated, and are already used for applications such as large televisions and lighting as well as small displays.
  • the hole transport layer is a hole transport layer and a hole injection layer
  • the light emitting layer is an electron block layer
  • the electron transport layer is an electron transport layer and an electron injection layer.
  • a co-deposited film doped with a metal, an organometallic compound, or another organic compound may be used as the carrier transport layer (electron transport layer or hole transport layer) of the organic electroluminescence device.
  • organic electroluminescent element materials cyclic azine compounds disclosed in Patent Document 1 or 2 have been reported.
  • organic electroluminescent elements have a higher driving voltage than inorganic light emitting diodes, have low luminance and luminous efficiency, have extremely low element lifetime, and have not been put into practical use.
  • recent organic electroluminescence devices have been gradually improved, further excellent materials are demanded in terms of luminous efficiency characteristics, driving voltage characteristics, and long life characteristics.
  • extremely high heat resistance may be required, and the material is required to have a high glass transition temperature (Tg).
  • Tg glass transition temperature
  • active research has been conducted on organic electroluminescent devices using thermally activated delayed fluorescence (TADF) and blue electroluminescent devices using phosphorescence by Adachi et al. In these materials for organic electroluminescence devices, high triplet excitation levels are required for energy confinement.
  • TADF thermally activated delayed fluorescence
  • Adachi et al In these materials for organic electroluminescence devices, high triplet excitation levels are required for energy confinement.
  • the cyclic azine compound having a non-planar structure disclosed in Patent Document 2 is required to be further improved in terms of extending the lifetime of the device when used in an organic electroluminescence device and increasing the luminous efficiency.
  • compounds containing triptycene specific synthesis examples, characteristics as an electron transport material for organic electroluminescence devices, glass transition temperature, and triplet excitation levels are not described, and their physical properties are unknown. It is.
  • each aspect of the present invention is to provide a cyclic azine compound having a high glass transition temperature and a high triplet excitation level, a material for an organic electroluminescence device, and an electron transport material for an organic electroluminescence device, as compared with conventionally known compounds. Is to provide.
  • cyclic azine compound (1) the glass transition temperature of a cyclic azine compound to which a group having a triptycene structure is bonded.
  • An organic electroluminescence device that is extremely high and has a high triplet excitation level and uses the compound as an electron transport material has a lower driving voltage, higher luminous efficiency, and higher performance than those using a conventionally known material. It has been found that the heat resistance is increased or the life is extended, and each aspect of the present invention has been completed.
  • the cyclic azine compound according to the first aspect of the present invention is a cyclic azine compound represented by the formula (1):
  • Ar 1 each independently represents a substituted or unsubstituted phenyl group, naphthyl group, or pyridyl group
  • Ar 2 is A substituted or unsubstituted monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, A monocyclic or condensed nitrogen-containing heteroaromatic group having 4 to 25 carbon atoms consisting of only a substituted or unsubstituted 6-membered ring, Represents a monocyclic or condensed heteroaromatic group having 3 to 25 carbon atoms composed of an atom selected from the group consisting of substituted or unsubstituted H, C, O, and S, or a hydrogen atom;
  • Ar 3 and Ar 4 are each independently Substituted or unsubstituted phenyl, naphthyl, pyridyl, Hydrogen atom, An unsubstituted alkyl group having 1 to 4 carbon atoms, or Represents a single bond
  • the cyclic azine compound according to the second aspect of the present invention is: The cyclic azine compound according to the first aspect, wherein Z is a nitrogen atom.
  • the cyclic azine compound according to the third aspect of the present invention is:
  • Two Ar 1 represent the same group and are a substituted or unsubstituted phenyl group, naphthyl group, or pyridyl group;
  • the substituent is the cyclic azine compound according to the first or second aspect, which is a fluorine atom, a methyl group, or a phenyl group.
  • the cyclic azine compound according to the fourth aspect of the present invention is: The cyclic azine compound according to any one of the first to third aspects, wherein two Ar 1 are both phenyl groups.
  • the cyclic azine compound according to the fifth aspect of the present invention is:
  • Ar 2 is A hydrogen atom, or Substituted or unsubstituted phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, benzofluorenyl, pyrenyl, perylenyl, fluoranthenyl, triphenylenyl, pyrimidyl, pyridyl, pyridyl, Quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group, When Ar 2 has a substituent, the substituent is a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or
  • the cyclic azine compound according to the sixth aspect of the present invention is: Ar 2 is a substituted or unsubstituted fluorenyl group, benzofluorenyl group, pyridyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, or dibenzothienyl group, When Ar 2 has a substituent, the substituent is a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms.
  • the cyclic azine compound according to any one of the first to fifth aspects which is an alkoxy group.
  • the cyclic azine compound according to the seventh aspect of the present invention is: Ar 3 and Ar 4 are each independently Hydrogen atom; Unsubstituted phenyl group, naphthyl group, pyridyl group; or A cyclic azine compound according to any one of the first to sixth aspects, wherein the single bond is bonded to X 2 .
  • the cyclic azine compound according to the eighth aspect of the present invention is: X 1 and X 2 are each independently Single bond;
  • the cyclic azine compound according to the ninth aspect of the present invention is: Y 1 , Y 2 , Y 3 , and Y 4 are all groups represented by C—R; Each R is independently Hydrogen atom; The unsubstituted alkyl group having 1 to 4 carbon atoms, the alkenyl group having 1 to 4 carbon atoms, the phenyl group, the naphthyl group, or the pyridyl group according to any one of the first to eighth embodiments. It is a cyclic azine compound.
  • the cyclic azine compound according to the tenth aspect of the present invention is: The cyclic azine compound according to any one of the first to ninth aspects, wherein W 1 , W 2 , and W 3 are all C—H.
  • the cyclic azine compound according to the eleventh aspect of the present invention is: A material for an organic electroluminescent element comprising the cyclic azine compound represented by the formula (1) according to any one of the first to tenth aspects.
  • the cyclic azine compound according to the twelfth aspect of the present invention is: An electron transport material for an organic electroluminescence device comprising the cyclic azine compound represented by the formula (1) according to any one of the first to tenth aspects.
  • a cyclic azine compound having excellent heat resistance of film quality and a high triplet excitation level, an organic electroluminescent device material containing the same, and an electron transport material for an organic electroluminescent device Therefore, it contributes to the provision of an organic electroluminescent device that is excellent in low driving voltage, high luminous efficiency, high heat resistance, or long life.
  • Each aspect of the present invention relates to a cyclic azine compound represented by the formula (1) (cyclic azine compound (1)), a method for producing the same, and a material for an organic electroluminescent element including the material.
  • the cyclic azine compound according to one embodiment of the present invention is a cyclic azine compound represented by the formula (1):
  • Ar 1 each independently represents a substituted or unsubstituted phenyl group, naphthyl group, or pyridyl group
  • Ar 2 is A substituted or unsubstituted monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, A monocyclic or condensed nitrogen-containing heteroaromatic group having 4 to 25 carbon atoms consisting of only a substituted or unsubstituted 6-membered ring, Represents a monocyclic or condensed heteroaromatic group having 3 to 25 carbon atoms composed of an atom selected from the group consisting of substituted or unsubstituted H, C, O, and S, or a hydrogen atom;
  • Ar 3 and Ar 4 are each independently Substituted or unsubstituted phenyl, naphthyl, pyridyl, Hydrogen atom, An unsubstituted alkyl group having 1 to 4 carbon atoms, or Represents a single bond
  • Ar 1 each independently represents a phenyl group, a naphthyl group, or a pyridyl group (these groups may be substituted with a fluorine atom, a methyl group, or a phenyl group).
  • the phenyl group, naphthyl group, or pyridyl group substituted with a fluorine atom in Ar 1 is not particularly limited, and examples thereof include a fluorophenyl group, a pentafluorophenyl group, a difluorophenyl group, a fluoronaphthyl group, and difluoro.
  • Preferred examples include a naphthyl group, a fluoropyridyl group, a difluoropyridyl group, and the like.
  • the phenyl group, naphthyl group, or pyridyl group substituted with a methyl group in Ar 1 is not particularly limited, and examples thereof include a tolyl group, a methylnaphthyl group, a dimethylphenyl group, a dimethylnaphthyl group, and a methylpyridyl group. Or a dimethylpyridyl group etc. are mentioned as a preferable example.
  • a phenyl group, a naphthyl group, or a pyridyl group substituted with a phenyl group in Ar 1 is not particularly limited. A group etc. are mentioned as a preferable example.
  • Ar 1 When two Ar 1 represent the same group and are substituted or unsubstituted phenyl group, naphthyl group, or pyridyl group, and Ar 1 has a substituent, the substituent is a fluorine atom, a methyl group Or a phenyl group.
  • Ar 1 is more preferably independently a phenyl group, a tolyl group, a naphthyl group, or a biphenyl group in terms of excellent electron transport material properties, and two Ar 1 are the same, It is more preferable that they are a group, a tolyl group, a naphthyl group, or a biphenyl group, and it is further more preferable that both two Ar ⁇ 1 > is a phenyl group from the viewpoint of easy synthesis.
  • Ar 1 preferably represents the same group in terms of easy synthesis.
  • Ar 1 is not particularly limited.
  • each of them independently represents a phenyl group, a p-tolyl group, an m-tolyl group, an o-tolyl group, a 2,4-dimethylphenyl group, 3, 5-dimethylphenyl group, mesityl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2,4-difluorophenyl group, 3,5-difluorophenyl group, biphenyl-2-yl group, Biphenyl-3-yl group, biphenyl-4-yl group, 1-naphthyl group, 2-naphthyl group, 1-phenylnaphthalen-2-yl group, 1-phenylnaphthalen-3-yl group, 1-phenylnaphthalene-4 -Yl group, 1-phenylnaphthalen-5-yl group, 1-phenylnaphthalen-6-yl
  • a naphthyl group is preferable, and each independently a phenyl group, a biphenyl-3-yl group, a biphenyl-4-yl group, a 1-naphthyl group, or a 2-naphthyl group is more preferable;
  • the group is particularly preferred.
  • Ar 2 is a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, a monocyclic or condensed nitrogen-containing heteroaromatic group having 4 to 25 carbon atoms consisting of only a 6-membered ring, or H, C, A monocyclic or condensed heteroaromatic group having 3 to 25 carbon atoms composed of an atom selected from an atomic group consisting of O and S (these groups include a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, A dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms), or a hydrogen atom.
  • the monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms in Ar 2 is not particularly limited, and examples thereof include a phenyl group, a naphthyl group, a phenanthryl group, an anthryl group, a pyrenyl group, and a triphenylenyl group.
  • Preferred examples include a chrysenyl group, a fluoranthenyl group, an acenaphthyl group, a fluorenyl group, or a benzofluorenyl group.
  • substituents are phenyl group, tolyl group, pyridyl group, methylpyridyl group, dimethylpyridyl group, fluorine atom, alkyl group having 1 to 4 carbon atoms, or alkoxy group having 1 to 4 carbon atoms. May be substituted.
  • a monocyclic or condensed nitrogen-containing heteroaromatic group having 4 to 25 carbon atoms consisting of only a 6-membered ring in Ar 2 is not particularly limited, and examples thereof include a pyridyl group, a pyrazyl group, a pyrimidyl group, and pyridazyl.
  • Preferred examples include a group, a quinolyl group, an isoquinolyl group, a phenanthridyl group, a benzoquinolyl group, or an acridinyl group.
  • the carbazolyl group is a heteroaromatic group including a 5-membered ring
  • the monocyclic or condensed nitrogen-containing heteroaromatic group having 4 to 25 carbon atoms and including only the 6-membered ring includes Not included.
  • these substituents include a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms. May be substituted.
  • a monocyclic or condensed heteroaromatic group having 3 to 25 carbon atoms composed of an atom selected from an atomic group consisting of H, C, O, and S in Ar 2 is not particularly limited.
  • a thienyl group, a furyl group, a bithienyl group, a bifuryl group, a benzothienyl group, a benzofuryl group, a dibenzothienyl group, a dibenzofuryl group, and the like are preferable examples.
  • substituents are phenyl group, tolyl group, pyridyl group, methylpyridyl group, dimethylpyridyl group, fluorine atom, alkyl group having 1 to 4 carbon atoms, or alkoxy group having 1 to 4 carbon atoms. May be substituted.
  • the alkyl group having 1 to 4 carbon atoms in Ar 2 is not particularly limited.
  • a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, or a t-butyl group is preferable. Take as an example.
  • the alkoxy group having 1 to 4 carbon atoms in Ar 2 is not particularly limited, and examples thereof include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, and a t-butoxy group. A preferred example is given.
  • Ar 2 represents a hydrogen atom, a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, a monocyclic or condensed nitrogen-containing heteroaromatic group having 4 to 25 carbon atoms consisting of only a 6-membered ring, or H 2 It is preferably a monocyclic or condensed heteroaromatic group having 3 to 25 carbon atoms composed of an atom selected from the group consisting of C, O, and S.
  • Ar 2 is a monocyclic or condensed aromatic hydrocarbon group having 6 to 24 carbon atoms, or a monocyclic or condensed ring containing nitrogen having 4 to 25 carbon atoms consisting of only a 6-membered ring because of its high glass transition temperature. It is preferably a heteroaromatic group or a monocyclic or condensed heteroaromatic group having 3 to 25 carbon atoms composed of an atom selected from the group consisting of H, C, O and S.
  • Ar 2 is a hydrogen atom; phenyl group, naphthyl group, biphenyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, Pyrimidyl group, pyrazyl group, pyridyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, or dibenzothienyl group (these groups are phenyl group, tolyl group, pyridyl group, methylpyridyl group, It may have a dimethylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms).
  • Ar 2 is phenyl group, naphthyl group, biphenyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, pyrimidyl group, pyrazyl group, pyridyl group Quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, or dibenzothienyl group (these groups are phenyl group, tolyl group, pyridyl group, methylpyridyl group, dimethylpyridyl group, fluorine atom, carbon More preferably an alkyl group having 1 to 4 carbon atoms or an alkoxy group having 1 to 4 carbon atoms).
  • Ar 2 is a phenyl group, naphthyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, pyrimidyl group, pyrazyl group, pyridyl group, quinolyl group And more preferably an isoquinolyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, a biphenyl group, a pyridylphenyl group, or a terphenyl group.
  • Ar 2 is excellent in electron transporting material characteristics, and is a fluorenyl group, benzofluorenyl group, pyridyl group, quinolyl group, isoquinolyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, or dibenzothienyl.
  • a group (these groups may have a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a fluorine atom, an alkyl group having 1 to 4 carbon atoms, or an alkoxy group having 1 to 4 carbon atoms).
  • Ar 2 is a pyridyl group.
  • Ar 2 Specific examples of these include, but are not limited to, hydrogen atom, phenyl group, p-tolyl group, m-tolyl group, o-tolyl group, 2,4-dimethylphenyl group, 3,5-dimethylphenyl group.
  • phenyl group p-tolyl group, biphenyl-2-yl group, biphenyl-3-yl group, biphenyl-4-yl group, 3- (2-pyridyl) phenyl group, 4- (2-pyridyl) phenyl group, 3- (3-pyridyl) phenyl group, 4- (3-pyridyl) phenyl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 2-phenylpyridine-6- Yl group, 2-phenylpyridin-5-yl group, 2-phenylpyridin-4-yl group, 3-phenylpyridin-5-yl group, 3-phenylpyridin-6-yl group, 2,6-diphenylpyridine- 4-yl group, 4,6-diphenylpyridin-2-yl group, 2-pyrimidyl group, 2-pyrazyl group, 1-naphthyl
  • Ar 3 and Ar 4 each independently represent a phenyl group, a naphthyl group, or a pyridyl group (these groups may be substituted with a fluorine atom, a methyl group, or a phenyl group), a hydrogen atom, or a carbon number.
  • the alkyl group having 1 to 4 carbon atoms in Ar 3 and Ar 4 is not particularly limited, but includes a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, or a t-butyl group Is a preferred example.
  • the phenyl group, naphthyl group, and pyridyl group substituted with a fluorine atom in Ar 3 and Ar 4 are not particularly limited, and examples thereof include the same groups as Ar 1 .
  • the phenyl group, naphthyl group, and pyridyl group substituted with a methyl group in Ar 3 and Ar 4 are not particularly limited, and examples thereof include the same groups as Ar 1 .
  • the phenyl group, naphthyl group, and pyridyl group substituted with a phenyl group in Ar 3 and Ar 4 are not particularly limited, and examples thereof include the same groups as Ar 1 .
  • Ar 3 and Ar 4 are each preferably a single bond formed with a hydrogen atom, a phenyl group, a naphthyl group, a biphenyl group, a pyridyl group, or X 2 independently from the viewpoint of excellent electron transporting material properties. Yes. Ar 3 and Ar 4 are each more preferably a hydrogen atom or a single bond formed with X 2 independently from the viewpoint of easy synthesis.
  • phenyl group, naphthyl group, or pyridyl group in Ar 3 and Ar 4 are particularly limited. Although it is not, the same group as Ar 1 is mentioned.
  • substituents phenyl group, biphenyl-3-yl group, biphenyl-4-yl group, 2-pyridyl group, 3-pyridyl group, 4-pyridyl group, 1 A -naphthyl group or a 2-naphthyl group is preferable, and a phenyl group is particularly preferable in terms of easy synthesis.
  • Ar 5 and Ar 6 are each independently a phenyl group, a naphthyl group, a pyridyl group (these groups may be substituted with a fluorine atom, a methyl group, or a phenyl group), a hydrogen atom, or a carbon atom.
  • the alkyl group having 1 to 4 carbon atoms in Ar 5 and Ar 6 is not particularly limited, but a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, a t-butyl group, or the like Is a preferred example.
  • the phenyl group, naphthyl group, and pyridyl group substituted with a fluorine atom in Ar 5 and Ar 6 are not particularly limited, and examples thereof include the same groups as Ar 1 .
  • the phenyl group, naphthyl group, and pyridyl group substituted with a methyl group in Ar 5 and Ar 6 are not particularly limited, and examples thereof include the same groups as Ar 1 .
  • the phenyl group, naphthyl group, and pyridyl group substituted with a phenyl group in Ar 5 and Ar 6 are not particularly limited, and examples thereof include the same groups as Ar 1 .
  • Ar 5 and Ar 6 are each independently preferably a hydrogen atom, a phenyl group, a tolyl group, a naphthyl group, a biphenyl group, or a pyridyl group because they are excellent in electron transporting material properties, and are easily synthesized. It is more preferable that it is a hydrogen atom at a point.
  • W 1 , W 2 , and W 3 each independently represent C—H or a nitrogen atom, and W 1 , W 2 , and W 3 all represent C—H, or W 1 , W 2 , W 3 represents a nitrogen atom, and the remaining two represent C—H. That is, W 1 , W 2 , and W 3 each independently represent C—H or a nitrogen atom, and at least two represent C—H. W 1 , W 2 and W 3 are all preferably C—H from the viewpoint of easy synthesis.
  • X 1 and X 2 are each independently a phenylene group, a naphthylene group, a biphenylene group, a pyridylene group (these groups may be substituted with a fluorine atom, a methyl group, or a phenyl group), or a single group. Represents a bond.
  • X 1 and X 2 are each independently Single bond; It is preferably an unsubstituted phenylene group, naphthylene group, biphenylene group, or pyridylene group. Of these groups, a single bond, a phenylene group, or a pyridylene group is more preferable independently from the viewpoint of easy availability of raw materials.
  • Z represents a nitrogen atom or C—H. Among these, it is preferable that Z is a nitrogen atom at the point which is excellent in an electron transport material characteristic.
  • Y 1 , Y 2 , Y 3 , and Y 4 each independently represent a group represented by C—R or a nitrogen atom.
  • R represents a phenyl group, a naphthyl group, or a pyridyl group (these groups may be substituted with a fluorine atom, a methyl group, or a phenyl group), a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, and a carbon number of 1 Represents -4 alkenyl groups.
  • any of Y 1 , Y 2 , Y 3 , and Y 4 represents a nitrogen atom
  • only one of Y 1 , Y 2 , Y 3 , and Y 4 is a nitrogen atom, and the rest is C
  • a group represented by -R (where each R independently represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an alkenyl group having 1 to 4 carbon atoms, a phenyl group, a naphthyl group, or a pyridyl group.
  • a naphthyl group, or a pyridyl group may be substituted with a fluorine atom, a methyl group, or a phenyl group), from the viewpoint of easy synthesis.
  • Y 1 , Y 2 , Y 3 , and Y 4 are all groups represented by C—R (where each R is independently a hydrogen atom or a group having 1 to 4 carbon atoms, for easy synthesis).
  • R may be bonded to each other to form an aromatic ring.
  • R couple bonded together and formed the aromatic ring.
  • Formula (1f) or (1g) etc. which are mentioned later are mentioned.
  • the compound represented by the formula (1) is not particularly limited.
  • the following formula (1a), (1b), (1c), (1d), (1e), (1f), or (1g) and the like can be embodied.
  • the cyclic azine compound (1) according to one embodiment of the present invention is used as a part of the constituent components of the organic electroluminescent 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 or a hole blocking layer.
  • Particular preferable compounds among the compounds represented by the formula (1) include the following (A-1) to (A-1356), but the present disclosure is not limited thereto.
  • the organic electroluminescent element material includes the cyclic azine compound (1).
  • 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 electroluminescent device includes a hole transport layer, an electron transport layer, an anode buffer layer, a cathode buffer layer, and the like in addition to the light emitting layer as necessary, and is sandwiched between the cathode and the anode. Take the structure. Specific examples include the structures shown below.
  • a conventionally known light emitting material can be used for the light emitting layer.
  • 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 light emitting layer can be obtained by dissolving a light emitting material in a solvent together with a binder such as a resin to form a solution and then applying the solution by a spin coating method to form a thin film.
  • 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.
  • the hole injection layer and the hole transport layer have a function of transmitting the holes injected from the anode to the light emitting layer, and the hole injection layer and the hole transport layer are interposed between the anode and the light emitting layer. Thus, many holes are injected into the light emitting layer with a lower electric field.
  • 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 preferably contains a cyclic azine compound represented by the above formula (1). Therefore, the electron transport material for organic electroluminescent elements according to one embodiment of the present invention includes the cyclic azine compound (1). In addition, about the cyclic azine compound (1) concerning 1 aspect of this invention, it can also be used other than the electron carrying layer of an organic electroluminescent element.
  • the electron transport layer may be formed by forming a cyclic azine compound represented by the above 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.
  • the electron transport layer preferably includes a cyclic azine compound represented by the formula (1), may include a conventionally known electron transport material, and has 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 light emitting material is not limited to the light emitting layer, and one kind may be contained in the hole transport layer or the electron transport layer adjacent to the light emitting layer, thereby further increasing the light emission efficiency of the organic electroluminescent device. be able to.
  • the type of substrate such as glass or plastic, and there is no particular limitation as long as it is transparent.
  • the substrate preferably used in the organic electroluminescent device according to one embodiment of the present invention include glass, quartz, and a light-transmitting 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 suitable example for producing an organic electroluminescent element will be described.
  • a method for producing an organic electroluminescent element composed of the anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / electron injection layer / cathode will be described.
  • 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 of the organic electroluminescent element 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 high 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.
  • the cathode those using an electrode substance of a metal having a small work function (4 eV or less) (referred to as an electron injecting metal), an alloy, an electrically conductive compound and a mixture thereof are preferably used.
  • electrode 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 ) Mixtures, indium, lithium / aluminum mixtures, rare earth metals and the like.
  • 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.
  • 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.
  • a thin film made of a substance is formed 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 50 to 200 nm, and a cathode is provided to obtain a desired organic electroluminescence device.
  • the organic electroluminescence device may be used as a kind of lamp for illumination or an exposure light source, or may be a projection device that projects an image, or directly recognizes a still image or a moving image. It may be used as a type of display device (display).
  • the driving method may be either a simple matrix (passive matrix) method or an active matrix method.
  • a full-color display device can be manufactured by using two or more organic electroluminescent elements according to one embodiment of the present invention having different emission colors.
  • the cyclic azine compound (1) according to one embodiment of the present invention is not particularly limited.
  • the following reaction formulas (1) to (1) (4) It can manufacture by the method shown by either.
  • compound (2a) the compound represented by formula (2a).
  • compound (2a) the compound represented by formula (2a).
  • compound (3a) compound (4a), compound (5a), compound (3b), compound (4b), compound (5b), compound (4c), compound (1g) and the like.
  • a 1 , A 2 , A 3 , and A 4 each represent a leaving group and are not particularly limited, and examples thereof include a chlorine atom, a bromine atom, an iodine atom, or a triflate independently.
  • a bromine atom or a chlorine atom is preferable independently from the viewpoint of good reaction yield.
  • M 1 , M 2 , M 3 , and M 4 each represent a leaving group and are not particularly limited.
  • said R ⁇ 1 > and R ⁇ 2 > respectively independently represents a chlorine atom, a bromine atom, or an iodine atom
  • said R ⁇ 3 > represents a C1-C4 alkyl group or a phenyl group
  • said R ⁇ 4 > is hydrogen atom, an alkyl group or a phenyl group having a carbon number of 1 to 4
  • B (oR 4) 2 two R 4 2 may be the same or different.
  • two R 4 may form a ring containing an oxygen atom and a boron atom together.
  • the ZnR 1, MgR 2, is not particularly limited, for example, ZnCl, ZnBr, ZnI, MgCl , MgBr, MgI like.
  • the Sn (R 3) 3, is not particularly limited, for example, Sn (Me) 3, Sn (Bu) 3 and the like.
  • B (OR 4 ) 2 is not particularly limited, and examples thereof include B (OH) 2 , B (OMe) 2 , B (O i Pr) 2 , and B (OBu) 2 .
  • B (OR 4 ) 2 in the case where two R 4s are combined to form a ring containing an oxygen atom and a boron atom include the following (C-1) to (C-6): The group shown can be exemplified, and the group shown by (C-2) is desirable from the viewpoint of good yield.
  • the compound (5a) used in the reaction formula (1) is, for example, J. Am. Chem. Soc. , 1963, 85 (10), 1549, WO2010 / 082621 Paragraph Nos. [0091] to [0103], or Japanese Unexamined Patent Publication No. 2013-223458, Paragraph Nos. [0045] to [0067] Can be manufactured in combination.
  • Reaction formula (1) is a method for obtaining the cyclic azine compound (1) according to one embodiment of the present invention by performing “Step 2” after “Step 1”.
  • “Step 1” is a method in which compound (2a) is reacted with compound (3a) in the presence or absence of a base in the presence of a palladium catalyst to obtain compound (4a).
  • Suzuki-Miyaura reaction By applying reaction conditions for general coupling reactions such as Negishi reaction, Tamao-Kumada reaction, Stille reaction, etc., the desired product can be obtained in good yield.
  • the palladium catalyst that can be used in “Step 1” is not particularly limited, and examples thereof 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.
  • a palladium complex having a tertiary phosphine as a ligand can also be prepared in a reaction system by adding a tertiary phosphine to a palladium salt or a complex compound.
  • the tertiary phosphine that can be used in this case is not particularly limited.
  • triphenylphosphine trimethylphosphine, tributylphosphine, tri (tert-butyl) phosphine, tricyclohexylphosphine, tert-butyldiphenylphosphine.
  • 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.
  • the base that can be used in “Step 1” is not particularly limited.
  • potassium carbonate is preferable in terms of a good yield.
  • the molar ratio of base to compound (3a) 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 (2a) to the compound (3a) used in “Step 1” is not particularly limited, but for example, 1: 2 to 5: 1 is desirable, and 1: 2 in terms of good yield. To 2: 1 is more desirable.
  • the solvent that can be used in “Step 1” is not particularly limited, and examples thereof include water, dimethyl sulfoxide, dimethylformamide, tetrahydrofuran, 1,4-dioxane, dimethoxyethane, toluene, benzene, diethyl ether, ethanol, Examples thereof include methanol or xylene, and these may be used in appropriate combination. It is desirable to use a mixed solvent of dioxane or tetrahydrofuran and water in terms of a good yield.
  • Step 1 is not particularly limited, but can be performed at a temperature appropriately selected from 0 ° C. to 150 ° C., for example, and is preferably performed at 50 ° C. to 100 ° C. in terms of good yield. desirable.
  • Compound (4a) 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.
  • Step 2 is a reaction of compound (4a) obtained in “Step 1” with compound (5a) in the presence or absence of a base and in the presence of a palladium catalyst.
  • This is a method for obtaining such a cyclic azine compound (1), which can be obtained in a high yield by applying reaction conditions of general coupling reactions such as Suzuki-Miyaura reaction, Negishi reaction, Tamao-Kumada reaction, Stille reaction and the like. The object can be obtained.
  • reaction conditions are not necessarily the same as those in “Step 1”.
  • reaction formula (2) After completion of “Step 2”, it may be purified by recrystallization, column chromatography, sublimation or the like, if necessary.
  • the reaction conditions in reaction formula (2) are the same as those in reaction formula (1). That is, “Step 3” in the reaction formula (2) is the same as the conditions listed in “Step 1” except that the compound (2a) is replaced with the compound (3b) and the compound (3a) is replaced with the compound (2b). Can be applied. The same reaction conditions as those mentioned in “Step 1” can be applied to “Step 4” in the reaction formula (2). After completion of “Step 4”, it may be purified by recrystallization, column chromatography, sublimation or the like, if necessary.
  • reaction conditions in Reaction Formula (3) are the same as those in Reaction Formula (1). That is, in “Step 5” in the reaction formula (3), compound (2a) was replaced with compound (5b) and compound (3a) was replaced with compound (4b) among the conditions listed in “Step 1”. Conditions can be applied. However, the reaction conditions are not necessarily the same as those in “Step 1”. After completion of “Step 5”, it may be purified by recrystallization, column chromatography, sublimation or the like, if necessary.
  • Reaction formula (4) is a method for obtaining the cyclic azine compound (1 g) according to one embodiment of the present invention by carrying out “Step 6”.
  • the reaction conditions in Reaction Formula (4) are the same as those in Reaction Formula (1). That is, in “Step 6” in the reaction formula (4), compound (2a) was replaced with compound (5a) and compound (3a) was replaced with compound (4c) among the conditions listed in “Step 1”. Conditions can be applied. However, the reaction conditions are not necessarily the same as those in “Step 1”. After completion of “Step 5”, it may be purified by recrystallization, column chromatography, sublimation or the like, if necessary.
  • Triplet excited level (eV) 1241.6 / ⁇ onset “ ⁇ onset” represents a wavelength value at the intersection of the tangent line and the horizontal axis by drawing a tangent line to the rising edge on the short wavelength side in the phosphorescence spectrum, where the vertical axis indicates the phosphorescence intensity and the horizontal axis indicates the wavelength.
  • the calculation of the triplet excited level by molecular orbital calculation was performed using Gaussian 09 (manufactured by Gaussian).
  • 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 LUMINANCEMETER (BM-9) (manufactured by TOPCON).
  • Table 1 shows the glass transition temperatures of the compounds obtained in Synthesis Example-1 to Synthesis Example-8 and Reference Example-1.
  • the cyclic azine compound according to one embodiment of the present invention to which a group having a triptycene structure is bonded has a high triplet excitation level.
  • the triplet excitation level in Table 2 is an actual measurement value measured using the aforementioned FP-6500 (manufactured by JASCO Corporation).
  • the triplet excited level in Table 3 is a value obtained by DFT calculation (B3LYP / 6-31G (d)) performed using Gaussian 09 (manufactured by Gaussian).
  • 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. First, the glass substrate was introduced into a vacuum evaporation tank, and the pressure was reduced to 1.0 ⁇ 10 ⁇ 4 Pa. Thereafter, as an organic compound layer on the glass substrate with an ITO transparent electrode shown by 1 in FIG. 6. The first electron transport layer 7, the second electron transport layer 8, and the cathode layer 9 were all formed by vacuum deposition while being laminated in this order.
  • ITO indium-tin oxide
  • a sublimated HIL film having a thickness of 55 nm was formed at a rate of 0.15 nm / second.
  • charge generation layer 3 sublimation-purified HAT was deposited to a thickness of 5 nm at a rate of 0.05 nm / second.
  • first hole transport layer 4 HTL-1 was deposited to a thickness of 10 nm at a rate of 0.15 nm / second.
  • second hole transport layer 5 HTL-2 was deposited 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).
  • ETL-1 was deposited to a thickness of 5 nm at a rate of 0.15 nm / second.
  • the cathode layer 9 is formed of silver / magnesium (weight ratio 1/10) and silver in this order at 80 nm (film formation rate 0.5 nm / second) and 20 nm (film formation rate 0.2 nm / second), respectively. And it was set as the 2 layer structure. 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.
  • a direct current was applied to the organic electroluminescent device produced as described above, and the light emission characteristics were evaluated using a luminance meter of LUMINANCE METER (BM-9) manufactured by TOPCON.
  • V voltage
  • cd / A current efficiency
  • element lifetime h
  • the element lifetime of Table 4 the luminance was measured decay time at the time of continuous lighting when driving was prepared device at an initial luminance 1000 cd / m 2, the luminance (cd / m 2) is required until reduced 10% Time was measured.
  • the voltage, current efficiency, and element lifetime were expressed as relative values based on the result in element reference example 1 described later as a reference value (100). The results are shown in Table 4.
  • Element Example-2 2- [3- (9,10-dihydro-9,10- [1,2] benzenoanthracen-2-yl) synthesized in Synthesis Example-2 in place of Compound A-257 in Device Example 1
  • An organic electroluminescent device was prepared in the same manner as in Device Example 1 except that ⁇ 5- (4-pyridyl) phenyl] -4,6-diphenyl-1,3,5-triazine (Compound A-337) was used. Prepared and evaluated. The results are shown in Table 4. Note that the voltage, current efficiency, and element lifetime were expressed as relative values with the result in element reference example-1 described later as the reference value (100).
  • Element Example-3 2- [3- (9,10-dihydro-9,10- [1,2] benzenoanthracen-2-yl) synthesized in Synthesis Example 3 instead of Compound A-257 in Device Example 1
  • An organic electroluminescent device was prepared in the same manner as in Device Example 1 except that -5- (3-quinolyl) phenyl] -4,6-diphenyl-1,3,5-triazine (Compound A-705) was used. Prepared and evaluated. The results are shown in Table 4. Note that the voltage, current efficiency, and element lifetime were expressed as relative values with the result in element reference example-1 described later as the reference value (100).
  • Element Example 4 2- [3- (9,10-dihydro-9,10- [1,2] benzenoanthracen-2-yl) synthesized in Synthesis Example 4 instead of Compound A-257 in Device Example 1
  • An organic electroluminescent device was prepared in the same manner as in Device Example 1 except that ⁇ 5- (4-isoquinolyl) phenyl] -4,6-diphenyl-1,3,5-triazine (Compound A-769) was used. Prepared and evaluated. The results are shown in Table 4. Note that the voltage, current efficiency, and element lifetime were expressed as relative values with the result in element reference example-1 described later as the reference value (100).
  • Element Example-6 In Device Example 1, 2- ⁇ 3- [4- (9,10-dihydro-9,10- [1,2] benzenoanthracene-2 synthesized in Synthesis Example-7 instead of Compound A-257 -Yl) -3-pyridyl] phenyl ⁇ -4,6-diphenyl-1,3,5-triazine (Compound A-8) was used to prepare an organic electroluminescent device in the same manner as in Device Example-1. Prepared and evaluated. The results are shown in Table 4. Note that the voltage, current efficiency, and element lifetime were expressed as relative values with the result in element reference example-1 described later as the reference value (100).
  • Element Example-7 2- ⁇ 3- [3- (9,10-dihydro-9,10- [1,2] benzenoanthracene-2 synthesized in Synthesis Example-8 instead of Compound A-257 in Device Example 1 -Il) -4-pyridyl] phenyl ⁇ -4,6-diphenyl-1,3,5-triazine (Compound A-11) was used to produce an organic electroluminescent device in the same manner as in Device Example-1. Prepared and evaluated. The results are shown in Table 4. Note that the voltage, current efficiency, and element lifetime were expressed as relative values with the result in element reference example-1 described later as the reference value (100).
  • Device reference example-1 In Device Example-1, instead of Compound A-257, 2- [5- (9-phenanthryl) -4 ′-(2-pyrimidyl) biphenyl-3-yl] described in JP2011-063584- 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 (ETL-2) was used. The results are shown in Table 4. For the voltage, current efficiency, and element lifetime, the result of this element reference example-1 was used as the reference value (100).
  • the cyclic azine compound (1) according to one embodiment of the present invention is extremely excellent in heat resistance of film quality, and by using the compound, an organic electroluminescent device excellent in long life and luminous efficiency can be provided. Moreover, the cyclic azine compound (1) concerning 1 aspect of this invention is utilized as an electron transport material for organic electroluminescent elements which is excellent in a low drive voltage. Furthermore, according to one embodiment of the present invention, an organic electroluminescent element having excellent power consumption can be provided. In addition, the cyclic azine compound according to one embodiment of the present invention is excellent in sublimation purification operability due to good thermal stability during sublimation purification, and provides a material with less impurities causing deterioration of the organic electroluminescence device. can do.
  • the cyclic azine compound according to one embodiment of the present invention is excellent in stability of a deposited film, an organic electroluminescent element having a long lifetime can be provided.
  • the thin film formed of the cyclic azine compound (1) according to one embodiment of the present invention is excellent in electron transport ability, hole blocking ability, redox resistance, water resistance, oxygen resistance, electron injection characteristics, etc. It is useful as an element material, and 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.
  • the cyclic azine compound (1) since the cyclic azine compound (1) according to one embodiment of the present invention has a wide band gap and a high triplet excitation level, it can be used not only for conventional fluorescent devices but also for phosphorescent devices and thermally activated delayed fluorescence ( It can be suitably used for an organic electroluminescent device using TADF).

Abstract

L'invention concerne un composé d'azine cyclique ayant une résistance thermique exceptionnelle, une durée de vie prolongée dans un élément électroluminescent organique, ainsi que d'excellentes propriétés de commande à basse tension ou une excellente efficacité lumineuse. L'invention concerne également un composé d'azine cyclique ayant une structure spécifique représentée par la formule (1).
PCT/JP2018/009952 2017-03-21 2018-03-14 Composé d'azine cyclique, matériau pour élément électroluminescent organique, et matériau de transport d'électrons pour élément électroluminescent organique WO2018173882A1 (fr)

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