WO2018123924A1 - Composition, matériau pour élément électroluminescent organique, film de composition, élément électroluminescent organique, et appareil électronique - Google Patents

Composition, matériau pour élément électroluminescent organique, film de composition, élément électroluminescent organique, et appareil électronique Download PDF

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WO2018123924A1
WO2018123924A1 PCT/JP2017/046297 JP2017046297W WO2018123924A1 WO 2018123924 A1 WO2018123924 A1 WO 2018123924A1 JP 2017046297 W JP2017046297 W JP 2017046297W WO 2018123924 A1 WO2018123924 A1 WO 2018123924A1
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group
substituted
carbon atoms
same
ring
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河村　昌宏
博之 岩渕
由美子 水木
均 熊
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出光興産株式会社
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    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to a composition, a material for an organic electroluminescence element, a composition film, an organic electroluminescence element, and an electronic apparatus.
  • Patent Document 1 and Patent Document 2 use a biscarbazole derivative having a specific structure having a cyano group as a first host and a compound having both a carbazolyl group derivative structure and a nitrogen-containing heteroaromatic ring as a second host.
  • Organic electroluminescent devices are described. According to this organic electroluminescence element, Patent Document 1 and Patent Document 2 describe a long life.
  • Patent Document 1 and Patent Document 2 when two materials (for example, a first host and a second host) are vapor-deposited from different vapor deposition sources, there is a problem that the manufacturing process of the organic electroluminescence element is complicated. . On the other hand, the lifetime of an organic electroluminescent element using one material (for example, only one of the first host and the second host) is shortened. Therefore, a technique for stably depositing two (or a plurality of) materials from one deposition source is desired. In the combination of the first host and the second host described in Patent Document 1 and Patent Document 2, when the deposition is performed from one deposition source, the ratio of the first host and the second host included in the formed layer is not stable. There is a problem that the performance of the organic electroluminescence element is not stable.
  • An object of the present invention is to provide a composition capable of stably depositing a ratio of materials from one vapor deposition source while maintaining the performance of the organic electroluminescence element, and an organic electroluminescence element including the composition Providing a material for use, providing a composition film containing the composition, providing an organic electroluminescence device containing the composition, and providing an electronic device including the organic electroluminescence device. .
  • Compositions containing a second compound are provided.
  • R 1 to R 4 are each independently A halogen atom, A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, A substituted or unsubstituted aryl group having 6 to 24 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 3 to 30 ring atoms; A silyl group substituted with one or more groups selected from the group consisting of an alkyl group having 1 to 25 carbon atoms and an aryl group having 6 to 24 ring carbon atoms, or a cyano group.
  • a is 2 or more, the plurality of R 1 are the same as or different from each other.
  • b is 2 or more, the plurality of R 2 are the same as or different from each other.
  • c is 2 or more, the plurality of R 3 are the same as or different from each other.
  • d is 2 or more, the plurality of R 4 are the same as or different from each other.
  • a 1 and A 2 are each independently A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 6 to 30 ring atoms.
  • a total of six ring structures represented by the following general formula (1a) are included in R 1 to R 4 , A 1 and A 2 .
  • X 1 , X 2 and X 3 each independently represent C R X or N. At least one of the six ring structures represented by the general formula (1a) In the ring structure, at least one of X 1 , X 2 and X 3 represents N. When the ring structures represented by the general formula (1a) are bonded to form a condensed ring, There are cases where it does not.
  • R X , R X1 , R X2 and R X3 are each independently Single bond, Hydrogen atom, A halogen atom, A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, A silyl group substituted with an alkyl group having 1 to 25 carbon atoms, or a cyano group.
  • the plurality of R X are the same as or different from each other. At least one of R X1 , R X2 , R X3 and one or more R X is a single bond.
  • R 21 to R 24 are each independently A halogen atom, A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 3 to 30 ring atoms; A silyl group substituted with one or more groups selected from the group consisting of an alkyl group having 1 to 25 carbon atoms and an aryl group having 6 to 30 ring carbon atoms, or a cyano group.
  • g 0, 1, 2, or 3.
  • h 0, 1, 2, 3, or 4.
  • the plurality of R 21 are the same as or different from each other.
  • the plurality of R 22 are the same as or different from each other.
  • the plurality of R 23 are the same as or different from each other.
  • the plurality of R 24 are the same as or different from each other.
  • At least one of A 3 and A 4 is a substituent represented by the following general formula (2a), and the other is a substituent represented by the following general formula (2b).
  • Ar represents a substituted or unsubstituted triphenylenylene group.
  • X 4 , X 5 , X 6 , X 7 and X 8 each independently represent CR Y or N.
  • R Y represents Hydrogen atom, A halogen atom, A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, A silyl group substituted with an alkyl group having 1 to 25 carbon atoms, or a cyano group.
  • the plurality of R Y are the same as or different from each other.
  • a material for an organic electroluminescence device comprising the composition according to one aspect of the present invention.
  • composition film including the composition according to the above-described aspect of the present invention.
  • An organic electroluminescent device comprising:
  • an electronic device equipped with the organic electroluminescence element according to one aspect of the present invention described above.
  • a composition capable of stably depositing a ratio of materials from one deposition source while maintaining the performance of the organic electroluminescence device, and to provide an organic including the composition.
  • composition is a composition in which two or more compounds are mixed.
  • the composition according to this embodiment contains at least a first compound represented by the following general formula (1) and a second compound represented by the following general formula (2).
  • the form of the composition according to the present embodiment is not particularly limited.
  • Examples of the form of the composition according to this embodiment include solids, powders, solutions, and films.
  • the composition according to this embodiment is a solid, it may be formed into a pellet.
  • the first compound is represented by the following general formula (1).
  • R 1 to R 4 are each independently A halogen atom, A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, A substituted or unsubstituted aryl group having 6 to 24 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 3 to 30 ring atoms; A silyl group substituted with one or more groups selected from the group consisting of an alkyl group having 1 to 25 carbon atoms and an aryl group having 6 to 24 ring carbon atoms, or a cyano group.
  • a is 2 or more, the plurality of R 1 are the same as or different from each other.
  • b is 2 or more, the plurality of R 2 are the same as or different from each other.
  • c is 2 or more, the plurality of R 3 are the same as or different from each other.
  • d is 2 or more, the plurality of R 4 are the same as or different from each other.
  • a 1 and A 2 are each independently A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 6 to 30 ring atoms.
  • a total of six ring structures represented by the following general formula (1a) are included in R 1 to R 4 , A 1 and A 2 .
  • X 1 , X 2 and X 3 each independently represent C R X or N. At least one of the six ring structures represented by the general formula (1a) In the ring structure, at least one of X 1 , X 2 and X 3 represents N. When the ring structures represented by the general formula (1a) are bonded to form a condensed ring, There are cases where it does not.
  • R X , R X1 , R X2 and R X3 are each independently Single bond, Hydrogen atom, A halogen atom, A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, A silyl group substituted with an alkyl group having 1 to 25 carbon atoms, or a cyano group.
  • the plurality of R X are the same as or different from each other. At least one of R X1 , R X2 , R X3 and one or more R X is a single bond.
  • a total of six ring structures represented by the general formula (1a) are included in R 1 to R 4 , A 1 and A 2 ” means R 1 to R 4.
  • a 1 and A 2 mean that six 6-membered rings represented by the general formula (1a) are contained.
  • the six 6-membered rings represented by the general formula (1a) are the same as or different from each other.
  • R 1 to R 4 A including the number of 6-membered rings constituting the condensed ring are included.
  • 6-membered ring means that it contains six in 1 and a 2.
  • the condensed ring includes two 6-membered rings. It will be out.
  • X A is CR 101 R 102 , NR 103 , an oxygen atom, or a sulfur atom.
  • R 101 to R 103 are each independently A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms.
  • Y 1 to Y 8 each independently represent CR X or N;
  • R X is Single bond, Hydrogen atom, A halogen atom, A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, A silyl group substituted with an alkyl group having 1 to 25 carbon atoms, or a cyano group.
  • R x When there are a plurality of R x , the plurality of R X are the same as or different from each other; At least one of the plurality of R X is a single bond.
  • the first compound is a compound represented by the following general formula (3).
  • R 1 to R 6 are each independently A halogen atom, A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, A silyl group substituted with an alkyl group having 1 to 25 carbon atoms, or a cyano group.
  • a is 0, 1, 2, 3, or 4;
  • b is 0, 1, 2, or 3;
  • c is 0, 1, 2, or 3;
  • d is 0, 1, 2, 3 or 4.
  • i is 0, 1, 2, 3, or 4.
  • j is 0, 1, 2, 3, 4, or 5.
  • the plurality of R 1 are the same as or different from each other.
  • the plurality of R 2 are the same as or different from each other.
  • the plurality of R 3 are the same as or different from each other.
  • the plurality of R 4 are the same as or different from each other.
  • i is 2 or more
  • the plurality of R 5 are the same as or different from each other.
  • j is 2 or more
  • the plurality of R 6 are the same as or different from each other.
  • B 1 represents a substituent represented by the following general formula (4) or the following general formula (5).
  • X 1 to X 3 each represent CR Z or a nitrogen atom.
  • R Z is Hydrogen atom, A halogen atom, A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, A silyl group substituted with an alkyl group having 1 to 25 carbon atoms, or a cyano group.
  • the plurality of R Z are the same as or different from each other.
  • R 7 to R 9 are each independently A halogen atom, A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, A cyano group is shown.
  • k is 0, 1, 2, 3, 4, or 5.
  • l is 0, 1, 2, 3, 4, or 5;
  • m is 0, 1, 2, 3, or 4.
  • the plurality of R 7 are the same as or different from each other.
  • the plurality of R 8 are the same as or different from each other.
  • m is 2 or more, the plurality of R 9 are the same as or different from each other.
  • the first compound is a compound represented by the following general formula (6).
  • R 1 to R 6 and R 10 are each independently A halogen atom, A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, A silyl group substituted with an alkyl group having 1 to 25 carbon atoms, or a cyano group.
  • a is 0, 1, 2, 3, or 4;
  • b is 0, 1, 2, or 3;
  • c is 0, 1, 2, or 3;
  • d is 0, 1, 2, or 3.
  • i is 0, 1, 2, or 3.
  • j is 0, 1, 2, 3, 4, or 5.
  • n is 0, 1, 2, 3, 4, or 5.
  • the plurality of R 1 are the same as or different from each other.
  • the plurality of R 2 are the same as or different from each other.
  • the plurality of R 3 are the same as or different from each other.
  • the plurality of R 4 are the same as or different from each other.
  • i is 2 or more
  • the plurality of R 5 are the same as or different from each other.
  • j is 2 or more
  • the plurality of R 6 are the same as or different from each other.
  • n is 2 or more, the plurality of R 10 are the same as or different from each other.
  • B 2 represents a substituent represented by the following general formula (7).
  • X 1 to X 3 each represent CR Z or a nitrogen atom.
  • R Z is Hydrogen atom, A halogen atom, A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, A silyl group substituted with an alkyl group having 1 to 25 carbon atoms, or a cyano group.
  • the plurality of R Z are the same as or different from each other.
  • R 11 and R 12 are each independently A halogen atom, A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, A silyl group substituted with an alkyl group having 1 to 25 carbon atoms, or a cyano group.
  • o is 0, 1, 2, 3, 4, or 5.
  • p is 0, 1, 2, 3, 4, or 5.
  • the plurality of R 11 are the same as or different from each other.
  • p is 2 or more, the plurality of R 12 are the same as or different from each other.
  • X 1 , X 2 , and X 3 in at least any one of the six ring structures represented by the general formula (1a) are preferably nitrogen atoms.
  • X 1 , X 2 , and X 3 are nitrogen atoms, and in the five ring structures, X 1 , X 2 , And X 3 are preferably CR Z , and R Z has the same meaning as described above.
  • one of A 1 and A 2 includes five 6-membered rings represented by the general formula (1a), and the other includes a 6-membered ring represented by the general formula (1a). It is also preferable that one is included.
  • one of A 1 and A 2 includes four 6-membered rings represented by the general formula (1a), and the other is a 6-membered represented by the general formula (1a). It is also preferred that two rings are included.
  • a, b, c and d are preferably 0.
  • i and j are preferably 0.
  • k, l and m are preferably 0.
  • n, o and p are preferably 0.
  • a, b, c, d, k, l, m, n, o and p are preferably 0.
  • Examples of the first compound according to this embodiment are shown below.
  • the first compound in the present invention is not limited to these specific examples.
  • R 21 to R 24 are each independently A halogen atom, A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 3 to 30 ring atoms; A silyl group substituted with one or more groups selected from the group consisting of an alkyl group having 1 to 25 carbon atoms and an aryl group having 6 to 30 ring carbon atoms, or a cyano group.
  • g 0, 1, 2, or 3.
  • h 0, 1, 2, 3, or 4.
  • the plurality of R 21 are the same as or different from each other.
  • the plurality of R 22 are the same as or different from each other.
  • the plurality of R 23 are the same as or different from each other.
  • the plurality of R 24 are the same as or different from each other.
  • At least one of A 3 and A 4 is a substituent represented by the following general formula (2a), and the other is a substituent represented by the following general formula (2b).
  • Ar represents a substituted or unsubstituted triphenylenylene group.
  • X 4 , X 5 , X 6 , X 7 and X 8 each independently represent CR Y or N.
  • R Y represents Hydrogen atom, A halogen atom, A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, A silyl group substituted with an alkyl group having 1 to 25 carbon atoms, or a cyano group.
  • the plurality of R Y are the same as or different from each other.
  • the second compound is a compound represented by the following general formula (8).
  • R 21 to R 24 are each independently A halogen atom, A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, A substituted or unsubstituted aryl group having 6 to 24 ring carbon atoms, A substituted or unsubstituted heterocyclic group having 3 to 30 ring atoms; A silyl group substituted with one or more groups selected from the group consisting of an alkyl group having 1 to 25 carbon atoms and an aryl group having 6 to 24 ring carbon atoms, or a cyano group.
  • g 0, 1, 2, or 3.
  • h 0, 1, 2, 3, or 4.
  • the plurality of R 21 are the same as or different from each other.
  • the plurality of R 22 are the same as or different from each other.
  • the plurality of R 23 are the same as or different from each other.
  • the plurality of R 24 are the same as or different from each other.
  • At least one of A 3 and A 4 is a substituent represented by the following general formula (2a), and the other is a substituent represented by (2b).
  • Ar represents a substituted or unsubstituted triphenylenylene group.
  • X 4 , X 5 , X 6 , X 7 and X 8 each independently represent CR Y or N.
  • R Y represents Hydrogen atom, A halogen atom, A substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, A substituted or unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms, A silyl group substituted with an alkyl group having 1 to 25 carbon atoms, or a cyano group.
  • the plurality of R Y are the same as or different from each other.
  • X 4 , X 5 , X 6 , X 7 and X 8 are CR Y
  • R Y is a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms.
  • a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 25 carbon atoms, a silyl group substituted with an alkyl group having 1 to 25 carbon atoms, or a cyano group, and a plurality of R Y are the same as each other Or different.
  • X 4 , X 5 , X 6 , X 7 and X 8 are preferably CR Y and RY is preferably a hydrogen atom.
  • Ar is preferably an unsubstituted divalent triphenylenylene group.
  • e, f, g and h are preferably 0.
  • Examples of the second compound according to this embodiment are shown below.
  • the second compound in the present invention is not limited to these specific examples.
  • composition of the present embodiment contains a combination of the first compound and the second compound, the composition of the present embodiment can be used while maintaining the performance of the organic electroluminescence device. It is possible to stably deposit the material ratio from the deposition source.
  • the blending ratio of the first compound and the second compound is not particularly limited. What is necessary is just to determine suitably the compounding ratio of a 1st compound and a 2nd compound according to the effect calculated
  • the compounding ratio (mass ratio) of the compound represented by the first compound: second compound is usually in the range of 1:99 to 99: 1, and preferably in the range of 10:90 to 90:10. 40:60 to 60:40 is more preferable.
  • the material for an organic electroluminescence element according to this embodiment includes the composition according to this embodiment. That is, the organic electroluminescent element material according to the present embodiment contains the first compound and the second compound. The material for an organic electroluminescence element according to this embodiment may further contain other compounds. When the organic electroluminescent element material according to the present embodiment further includes other compounds, the other compounds may be solid or liquid.
  • composition film includes the composition according to the present embodiment. That is, the film (composition film) containing the composition according to the present embodiment means a film containing the first compound and the second compound.
  • the composition film according to the present embodiment may further contain other compounds.
  • the method for forming the composition film according to the present embodiment is not particularly limited unless otherwise specified in the present specification.
  • known methods such as a dry film forming method and a wet film forming method can be employed.
  • the dry film forming method include a vacuum deposition method, a sputtering method, a plasma method, and an ion plating method.
  • wet film forming method include a spin coating method, a dipping method, a flow coating method, and an ink jet method.
  • the organic EL element according to this embodiment includes an organic layer between a pair of electrodes.
  • This organic layer includes at least one layer composed of an organic compound.
  • the organic layer is formed by laminating a plurality of layers composed of organic compounds.
  • the organic layer may further contain an inorganic compound.
  • at least one of the organic layers is a light emitting layer. Therefore, the organic layer may be composed of, for example, a single light emitting layer or may include a layer that can be employed in an organic EL element.
  • the layer that can be employed in the organic EL element is not particularly limited. For example, at least one selected from the group consisting of a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and a barrier layer. Layer.
  • the organic layer is preferably composed of a plurality of layers, and the composition according to this embodiment is preferably contained in one or more of the plurality of layers.
  • the composition according to this embodiment in any one or more layers of the organic EL element according to this embodiment, high organic EL performance (for example, light emission performance of at least one of driving voltage, light emission efficiency, and lifetime) ) Can be obtained.
  • the composition according to the present embodiment is formed using the method according to the present embodiment (for example, vacuum deposition method)
  • the first compound and the second compound in the light emitting layer from the initial deposition stage to the final deposition stage.
  • the material ratio with the compound is stable.
  • the organic EL element can stably maintain high light emission performance regardless of the deposition time.
  • the light emitting layer preferably contains the composition according to this embodiment.
  • a hole transport layer is further provided between the anode and the light emitting layer.
  • the composition according to an embodiment of the present invention is used in the electron transport zone.
  • the structure of (d) is preferably used.
  • the “light emitting layer” is an organic layer having a light emitting function.
  • the “hole injection / transport layer” means “at least one of a hole injection layer and a hole transport layer”.
  • the “electron injection / transport layer” means “at least one of an electron injection layer and an electron transport layer”.
  • a hole injection layer is provided between the hole transport layer and the anode.
  • an organic EL element has an electron injection layer and an electron carrying layer, it is preferable that the electron injection layer is provided between the electron carrying layer and the cathode.
  • each of the hole injection layer, the hole transport layer, the electron transport layer, and the electron injection layer may be composed of a single layer or a plurality of layers.
  • FIG. 1 shows a schematic configuration of an example of the organic EL element according to this embodiment.
  • the organic EL element 1 includes a translucent substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4.
  • the organic layer 10 includes a hole injection layer 6, a hole transport layer 7, a light emitting layer 5, an electron transport layer 8, and an electron injection layer 9.
  • a hole injection layer 6, a hole transport layer 7, a light emitting layer 5, an electron transport layer 8, and an electron injection layer 9 are laminated in this order from the anode 3 side.
  • the light emitting layer 5 of the organic EL element 1 contains the composition according to the present embodiment. That is, the light emitting layer 5 includes the first compound and the second compound.
  • the organic EL device of the present embodiment is driven at a low voltage by using the first compound and the second compound in combination in the organic layer. From the viewpoint of driving the organic EL element at a low voltage, an embodiment in which the first compound and the second compound are contained in one light emitting layer is preferable.
  • the ratio of the total mass of the first compound and the second compound contained in the organic layer is preferably 1% by mass or more and 100% by mass or less.
  • the blending ratio of the first compound and the second compound is not particularly limited. What is necessary is just to determine suitably the compounding ratio of a 1st compound and a 2nd compound according to the effect calculated
  • the compounding ratio (mass ratio) of the compound represented by the first compound: second compound is usually in the range of 1:99 to 99: 1, and preferably in the range of 10:90 to 90:10. 40:60 to 60:40 is more preferable.
  • the light emitting layer preferably further contains a light emitting material.
  • the light emitting layer contains a phosphorescent material as a light emitting material.
  • the phosphorescent material is preferably an orthometalated complex of any metal atom selected from the group consisting of iridium (Ir), osmium (Os), and platinum (Pt). Suitable phosphorescent materials will be described later.
  • the content of the light emitting material in the light emitting layer is preferably 0.1% by mass or more and 50% by mass or less. % To 20% by mass is more preferable.
  • each layer of the organic EL element which is one embodiment of the present invention is not particularly limited unless otherwise specified in the present specification.
  • known methods such as a dry film forming method and a wet film forming method can be employed.
  • the dry film forming method include a vacuum deposition method, a sputtering method, a plasma method, and an ion plating method.
  • the wet film forming method include a spin coating method, a dipping method, a flow coating method, and an ink jet method.
  • the film thickness of each layer of the organic EL element which is one embodiment of the present invention is not limited except as specifically mentioned above.
  • the film thickness of each layer needs to be set to an appropriate film thickness. If the film thickness is too thick, a large applied voltage is required to obtain a constant light output, and the efficiency may deteriorate. If the film thickness is too thin, pinholes and the like are generated, and there is a possibility that sufficient light emission luminance cannot be obtained even when an electric field is applied.
  • the film thickness is suitably in the range of 5 nm to 10 ⁇ m, more preferably in the range of 10 nm to 0.2 ⁇ m.
  • the substrate is used as a support for the light emitting element.
  • the substrate for example, glass, quartz, plastic, or the like can be used.
  • a flexible substrate may be used.
  • the flexible substrate is a substrate that can be bent (flexible), and examples thereof include a plastic substrate made of polycarbonate or polyvinyl chloride.
  • anode For the anode formed on the substrate, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a high work function (specifically, 4.0 eV or more).
  • a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a high work function (specifically, 4.0 eV or more).
  • ITO indium tin oxide
  • ITO indium oxide-tin oxide containing silicon or silicon oxide
  • indium oxide-zinc oxide silicon oxide
  • tungsten oxide and indium oxide containing zinc oxide.
  • graphene graphene.
  • gold (Au), platinum (Pt), a nitride of a metal material (for example, titanium nitride), or the like can be given.
  • the hole injection layer is a layer provided for efficiently injecting holes from the anode into the organic layer.
  • Substances used for the hole injection layer include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide
  • An oxide, a tungsten oxide, a manganese oxide, an aromatic amine compound, an acceptor compound, a polymer compound (oligomer, dendrimer, polymer, etc.), or the like can also be used.
  • the substance used for the hole injection layer is preferably an aromatic amine derivative or an acceptor compound, and more preferably an acceptor compound.
  • a heterocyclic derivative substituted with an electron withdrawing group a quinone derivative substituted with an electron withdrawing group, an arylborane derivative, a heteroarylborane derivative, or the like is preferably used.
  • hexacyanohexaazatriphenylene, F 4 TCNQ (2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane) or 1,2,3-tris [(cyano) (4-cyano-2,3 , 5,6-tetrafluorophenyl) methylene] cyclopropane and the like are preferably used.
  • the layer containing an acceptor compound is preferably in a form further containing a matrix material.
  • a wide variety of materials for organic EL can be used as the matrix material.
  • a donor compound is preferably used, and an aromatic amine compound is more preferably used.
  • the hole transport layer is a layer containing a substance having a high hole transport property.
  • An aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used for the hole transport layer.
  • a high molecular compound such as poly (N-vinylcarbazole) (abbreviation: PVK) or poly (4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.
  • PVK N-vinylcarbazole
  • PVTPA poly (4-vinyltriphenylamine)
  • the layer containing a substance having a high hole-transport property is not limited to a single layer, and two or more layers containing the above substances may be stacked.
  • the hole transport material is preferably a compound represented by the following general formula (H).
  • Ar 1 to Ar 3 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms. Or a group composed of a combination of a substituted or unsubstituted aryl group and a substituted or unsubstituted heterocyclic group.
  • aryl group a phenyl group, a biphenyl group, a terphenyl group, a fluorenyl group, a spirobifluorenyl group, an indenofluorenyl group, a naphthyl group, a phenanthryl group, an anthryl group, a triphenylenyl group and the like are preferable.
  • heterocyclic group a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group and the like are preferable.
  • At least one of Ar 1 to Ar 3 in the general formula (H) is preferably a compound further substituted with an arylamino group, and is a diamine derivative, a triamine derivative, or a tetraamine derivative. It is also preferable.
  • diamine derivatives examples include tetraaryl-substituted benzidine derivatives and TPTE (4,4′-bis [N-phenyl-N- [4′-diphenylamino-1,1′-biphenyl-4-yl] amino] -1,1 '-Biphenyl] and the like are preferably used.
  • the hole transporting material used for the layer in contact with the phosphorescent light emitting layer preferably has a high triplet level, and Ar 1 to Ar 3 in the general formula (H) are fluorenyl group, spirofluorenyl group, phenyl group.
  • a group formed by a substituent such as a biphenyl group, a phenanthryl group, a triphenylenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a combination thereof.
  • the light-emitting layer is a layer including a substance having high light-emitting properties, and various materials can be used.
  • the light emitting layer usually contains a light emitting material (dopant material) having a high light emitting property and a host material for efficiently emitting light.
  • a fluorescent compound that emits fluorescence or a phosphorescent compound that emits phosphorescence can be used as the substance having high light-emitting property.
  • a fluorescent compound is a compound that can emit light from a singlet excited state
  • a phosphorescent compound is a compound that can emit light from a triplet excited state.
  • the light emitting layer containing a fluorescent compound is called a fluorescent light emitting layer
  • the light emitting layer containing a phosphorescent compound is called a phosphorescent light emitting layer.
  • Fluorescent compounds can be widely used as dopant materials for the fluorescent layer.
  • the dopant material for the fluorescent light emitting layer among them, condensed polycyclic aromatic derivatives, styrylamine derivatives, condensed ring amine derivatives, boron-containing compounds, pyrrole derivatives, indole derivatives, carbazole derivatives, and the like are preferable. More preferable examples of the dopant material for the fluorescent light emitting layer include condensed ring amine derivatives and boron-containing compounds.
  • Examples of the condensed ring amine derivative include diaminopyrene derivatives, diaminochrysene derivatives, diaminoanthracene derivatives, diaminofluorene derivatives, and diaminofluorene derivatives in which one or more benzofuro skeletons are condensed.
  • Examples of the boron-containing compound include a pyromethene derivative and a triphenylborane derivative.
  • the term “derivative” refers to a compound that includes the skeleton as a partial structure, and includes a compound that forms a further condensed ring and a compound that forms a ring between substituents.
  • a condensed polycyclic aromatic derivative it is a compound that contains a condensed polycyclic aromatic skeleton as a partial structure, a compound that further forms a condensed ring in the condensed polycyclic aromatic skeleton, and the condensed polycyclic aromatic Also included are compounds that form a ring with substituents of the skeleton.
  • a general fluorescent material can be used as a host material used for the fluorescent light emitting layer.
  • the host material used for the fluorescent light-emitting layer is preferably a compound having a condensed polycyclic aromatic derivative as a main skeleton, and particularly preferably an anthracene derivative, a pyrene derivative, a chrysene derivative, or a naphthacene derivative.
  • a host particularly suitable as a blue host material (a host material used with a blue fluorescent light-emitting dopant material) and a green host material (a host material used with a green fluorescent light-emitting dopant material) is represented by the following general formula (X). It is an anthracene derivative represented.
  • Ar X1 and Ar X2 each independently represent a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted ring atom having 3 to 50 ring atoms.
  • a heterocyclic group is shown.
  • Ar X1 and Ar X2 each independently preferably represent a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms or a heterocyclic group having 5 to 30 ring atoms.
  • a metal complex such as an iridium complex, an osmium complex, or a platinum complex is used.
  • the phosphorescent material that is an orthometalated complex of a metal atom selected from the group consisting of iridium (Ir), osmium (Os), and platinum (Pt) is a complex represented by the following formula ( ⁇ ). preferable.
  • M represents at least one metal selected from the group consisting of osmium, iridium and platinum, and n represents the valence of the metal.
  • Ring A 1 represents a substituted or unsubstituted aryl group having 6 to 24 ring carbon atoms or a heteroaryl group having 5 to 30 ring atoms
  • Ring A 2 is a substituted group containing nitrogen as a hetero ring forming atom. Alternatively, it represents an unsubstituted heteroaryl group having 5 to 30 ring atoms.
  • Examples of the aryl group having 6 to 24 ring carbon atoms in the ring A 1 of the formula ( ⁇ ) include the aryl groups in the general formula (1) described above.
  • Examples of the heteroaryl group having 5 to 30 ring atoms in the ring A 1 and the ring A 2 of the formula ( ⁇ ) include the heteroaryl groups in the general formula (1) described above.
  • the substituent that the ring A 1 and the ring A 2 of the formula ( ⁇ ) may have is the same as the substituent in the general formula (1) described above.
  • the complex represented by the formula ( ⁇ ) is preferably a complex represented by the following formula (T) or (U).
  • M represents a metal
  • ring B and ring C each independently represent an aryl group or heteroaryl group having 5 or 6 ring atoms.
  • Ring A-ring B represents a bond pair of an aryl group or a heteroaryl group, and is coordinated to the metal M through the nitrogen atom of ring A and the sp 2 hybrid atom of ring B.
  • Ring A to ring C represent a bond pair of an aryl group or a heteroaryl group.
  • R a , R b and R c are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms, a substituted or unsubstituted group; Amino group, substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 25 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, substituted or unsubstituted This represents any one selected from the group consisting of an aryl group having 6 to 24 ring carbon atoms and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms, and R a is 1 or more and 4 or less R b is 1 or more and 4 or less, R c is 1 or more and 4 or less
  • X 1 to X 9 each independently represents a carbon atom or a nitrogen atom.
  • R d and R e are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 25 carbon atoms, a substituted or unsubstituted amino group, Substituted or unsubstituted alkenyl group having 2 to 25 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 25 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, substituted or unsubstituted ring-forming carbon R c , R d and R e bonded to the ring C, each represented by any one selected from the group consisting of an aryl group having 6 to 24 and a substituted or unsubstituted heteroaryl group having 5 to 30 ring
  • examples of M include osmium, iridium, and platinum, and iridium is particularly preferable.
  • examples of the aryl group having 5 or 6 ring atoms represented by ring B and ring C include the aryl group in the general formula (1) described above.
  • Examples of the heteroaryl group having 5 or 6 ring atoms represented by ring B and ring C include the heteroaryl group in the general formula (1) described above.
  • the aralkyl group having 7 to 50 carbon atoms, the substituted or unsubstituted aryl group having 6 to 24 ring carbon atoms and the substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms are as described above. The same group is mentioned.
  • Examples of the monoanionic bidentate ligand represented by L ′ include a ligand represented by the following formula (L ′).
  • X 4 ⁇ X 9, R a, and R b are the same as X 4 ⁇ X 9, R a , and R b in Formula (T), preferable embodiments thereof are also the same.
  • the ligand represented by the formula (L ′) is represented by the formula (T) through a solid line extending from the ring X 9 to the outside of the ring B and a broken line extending from the nitrogen atom of the ring A to the outside of the ring A. Coordinates to metal M.
  • X represents any one selected from the group consisting of NR, oxygen atom, sulfur atom, BR, and selenium atom
  • R represents a hydrogen atom or a substituted or unsubstituted carbon number of 1 to 25 It is an alkyl group.
  • R 1 , R 2 , R 3 and R 4 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 24 ring carbon atoms.
  • R 1 is 1 or more and 4 or less
  • R 2 is 1 or more and 4 or less
  • R 3 is 1 or more and 4 or less
  • R 4 is 1 or more and 4 or less
  • the numbers of R 1 , R 2 , R 3 and R 4 are independent of each other.
  • examples of the alkyl group having 1 to 25 carbon atoms represented by R, R 1 , R 2 , R 3 and R 4 include the groups described above, and preferred embodiments thereof are also the same.
  • examples of the aryl group having 6 to 24 ring carbon atoms represented by R 1 , R 2 , R 3, and R 4 include the groups described above, and preferred embodiments thereof are also the same.
  • an iridium complex represented by the following formula ( ⁇ ) is also preferable.
  • a 1 to A 8 contain a carbon atom or a nitrogen atom, at least one of A 1 to A 8 is a nitrogen atom, ring B is bonded to ring A by a C—C bond, and iridium (Ir) is bonded to ring A through an Ir—C bond.
  • Ir iridium
  • a 3 and A 4 are carbon atoms among A 1 to A 4 .
  • a 5 is preferably a nitrogen atom
  • a 1 to A 4 and A 6 to A 8 are preferably carbon atoms.
  • a 6 is preferably CR (carbon atom to which R is bonded), and R is a substituted or unsubstituted alkyl group having 1 to 25 carbon atoms or a substituted or unsubstituted cycloalkyl group having 3 to 25 ring carbon atoms.
  • R is preferably a substituted or unsubstituted alkyl having 1 to 25 carbon atoms or a substituted or unsubstituted cycloalkyl having 3 to 25 ring carbon atoms.
  • R 1 to R 4 are each independently mono-substituted, di-substituted, tri-substituted or tetra-substituted, or unsubstituted, and adjacent R 1 to R 4 are bonded to each other.
  • R 1 to R 4 are each independently hydrogen, deuterium, halogen, Substituted or unsubstituted alkyl having 1 to 25 carbon atoms, Substituted or unsubstituted cycloalkyl having 3 to 25 ring carbon atoms, Substituted or unsubstituted heteroalkyl having 2 to 25 atoms, Substituted or unsubstituted arylalkyl having 7 to 50 carbon atoms, Substituted or unsubstituted alkoxy having 1 to 25 carbon atoms, Substituted or unsubstituted aryloxy having 6 to 24 ring carbon atoms, Substituted or unsubstituted amino, Substituted silyl, Substituted or unsubstituted alkenyl having 2 to 25 carbon atoms, Cycloalkenyl having 3 to 25 ring carbon atoms, Heteroalkenyl having 3
  • the substituted carbonyl is a carbonyl substituted with one or more groups selected from the group consisting of an alkyl group having 1 to 25 carbon atoms and an aryl group having 6 to 24 ring carbon atoms.
  • R 1 to R 4 are preferably each independently selected from the group consisting of hydrogen, deuterium, alkyl having 1 to 25 carbon atoms, and combinations thereof.
  • At least one of R 2 and R 3 is preferably an alkyl group having 1 to 25 carbon atoms, more preferably the alkyl group is deuterated or partially deuterated.
  • n is an integer of 1 to 3, and is preferably 1.
  • the complex represented by the formula ( ⁇ ) in addition to the complex represented by the formula (T) or (U), the complex represented by the following formula (V), (X), (Y) or (Z) It can also be used.
  • R 50 to R 54 are each independently a hydrogen atom or a substituent, k is an integer of 1 to 4, and 1 is 1 Is an integer from 4 to 4, and m is an integer from 1 to 2. M is Ir, Os, or Pt. Examples of the substituent represented by R 50 to R 54 are the same as those described above.
  • Formula (V) is preferably represented by the following formula (V-1), and formula (X) is preferably represented by the following formula (X-1) or formula (X-2).
  • R 50 , k, and M are the same as R 50 , k, and M described above.
  • the host material used for the phosphorescent light-emitting layer is preferably a material having a triplet level higher than that of the phosphorescent dopant, and a phosphorescent host material such as a general aromatic derivative, heterocyclic derivative, or metal complex is used. Can do.
  • aromatic derivatives and heterocyclic derivatives are preferable, and examples of aromatic derivatives include naphthalene derivatives, triphenylene derivatives, phenanthrene derivatives, and fluoranthene derivatives.
  • Examples include indole derivatives, carbazole derivatives, pyridine derivatives, pyrimidine derivatives, triazine derivatives, quinoline derivatives, isoquinoline derivatives, quinazoline derivatives, dibenzofuran derivatives, and dibenzothienyl derivatives.
  • the derivative is defined as described above.
  • One preferred form of the host material used for the phosphorescent light emitting layer is a composition according to an embodiment of the present invention.
  • the electron transport layer is a layer containing a substance having a high electron transport property.
  • one or more layers may be provided between the electron transport layer and the light emitting layer.
  • This layer is called a second electron transport layer, a hole blocking layer, a triplet block layer, or the like.
  • a material having a deep HOMO level In order to improve the triplet blocking property, it is preferable to use a material having a high triplet level.
  • the electron transport layer includes metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, heterocyclic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, condensed aromatic hydrocarbon derivatives, and Polymeric compounds can be used.
  • metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes
  • heterocyclic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, condensed aromatic hydrocarbon derivatives, and Polymeric compounds can be used.
  • imidazole derivatives for example, benzimidazole derivatives, imidazopyridine derivatives, benzimidazophenanthridine derivatives
  • azine derivatives for example, pyrimidine derivatives, triazine derivatives, quinoline derivatives, isoquinoline derivatives, phenanthroline derivatives, etc., and these heterocyclic rings Phosphine oxide-based substituents
  • aromatic hydrocarbon derivatives for example, anthracene derivatives and fluoranthene derivatives.
  • the composition according to one embodiment of the present invention can be used.
  • the electron transport layer is formed of an alkali metal derivative (for example, lithium quinolinate complex) such as an alkali metal (Li, Cs, etc.), an alkaline earth metal (Mg, etc.), and an alloy containing these. And at least one selected from the group consisting of alkaline earth metal derivatives.
  • an alkali metal derivative for example, lithium quinolinate complex
  • the electron transport layer contains at least one of alkali metals, alkaline earth metals and alloys thereof, the content ratio in the electron transport layer is preferably 0.1 to 50% by mass, more preferably 0.1 to 20%.
  • the content ratio in the electron transport layer is preferably It is 1 to 99% by mass, more preferably 10 to 90% by mass.
  • the electron injection layer is a layer containing a substance having a high electron injection property.
  • alkali metals such as lithium (Li), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF 2 ), lithium oxide (LiO x ), and the like are used.
  • Alkali metal derivatives for example, lithium quinolinate complexes
  • alkaline earth metal derivatives such as metals or alloys containing them can be used.
  • cathode For the cathode, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a small work function (specifically, 3.8 eV or less).
  • cathode materials include elements belonging to Group 1 or Group 2 of the Periodic Table of Elements, that is, alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth such as magnesium (Mg). And other rare earth metals such as alloys, alloys containing them (for example, MgAg, AlLi), and alloys containing these.
  • the hydrogen atom includes isotopes having different neutron numbers, that is, light hydrogen (protium), deuterium (triuterium), and tritium.
  • the number of ring-forming carbon atoms constitutes the ring itself of a compound having a structure in which atoms are bonded cyclically (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, or a heterocyclic compound). Represents the number of carbon atoms in the atom.
  • the carbon contained in the substituent is not included in the number of ring-forming carbons.
  • the “ring-forming carbon number” described below is the same unless otherwise specified.
  • the benzene ring has 6 ring carbon atoms
  • the naphthalene ring has 10 ring carbon atoms
  • the pyridinyl group has 5 ring carbon atoms
  • the furanyl group has 4 ring carbon atoms.
  • the carbon number of the alkyl group is not included in the number of ring-forming carbons.
  • the carbon number of the fluorene ring as a substituent is not included in the number of ring-forming carbons.
  • the number of ring-forming atoms means a compound (for example, a monocyclic compound, a condensed ring compound, a bridging compound, a carbocyclic compound, a heterocycle) having a structure in which atoms are bonded in a cyclic manner (for example, a monocyclic ring, a condensed ring, or a ring assembly).
  • a compound for example, a monocyclic compound, a condensed ring compound, a bridging compound, a carbocyclic compound, a heterocycle
  • a cyclic manner for example, a monocyclic ring, a condensed ring, or a ring assembly.
  • Atoms that do not constitute a ring or atoms included in a substituent when the ring is substituted by a substituent are not included in the number of ring-forming atoms.
  • the “number of ring-forming atoms” described below is the same unless otherwise specified.
  • the pyridine ring has 6 ring atoms
  • the quinazoline ring has 10 ring atoms
  • the furan ring has 5 ring atoms.
  • a hydrogen atom bonded to a carbon atom of a pyridine ring or a quinazoline ring or an atom constituting a substituent is not included in the number of ring-forming atoms.
  • a fluorene ring is bonded to the fluorene ring as a substituent (including a spirofluorene ring)
  • the number of atoms of the fluorene ring as a substituent is not included in the number of ring-forming atoms.
  • the “carbon number XX to YY” in the expression “substituted or unsubstituted ZZ group having XX to YY” represents the number of carbon atoms in the case where the ZZ group is unsubstituted. The carbon number of the substituent in the case where it is present is not included.
  • atom number XX to YY in the expression “a ZZ group having a substituted or unsubstituted atom number XX to YY” represents the number of atoms when the ZZ group is unsubstituted. In this case, the number of substituent atoms is not included.
  • unsubstituted in the case of “substituted or unsubstituted” means that a hydrogen atom is bonded without being substituted with the above substituent.
  • alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, pentyl (including isomeric groups), hexyl Groups (including isomer groups), heptyl groups (including isomer groups), octyl groups (including isomer groups), nonyl groups (including isomer groups), decyl groups (including isomer groups), undecyl Groups (including isomer groups), dodecyl groups (including isomer groups), and the like.
  • a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, and a pentyl group (all including an isomer group) are preferable.
  • Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group and t-butyl group are more preferable, and methyl group, ethyl group, isopropyl group and t-butyl group are particularly preferable. preferable.
  • the carbon number of the alkyl group is 1 to 25, preferably 1 to 10.
  • halogenated alkyl group in which the alkyl group is substituted with a halogen atom examples include groups in which the alkyl group having 1 to 25 carbon atoms is substituted with one or more halogen atoms, preferably a fluorine atom.
  • Specific examples of the halogenated alkyl group having 1 to 25 carbon atoms in the present specification include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, a trifluoromethylmethyl group, a trifluoroethyl group, A pentafluoroethyl group etc. are mentioned.
  • the alkenyl group is a group having a double bond in the alkyl group, and the alkenyl group has 2 to 25 carbon atoms, preferably 2 to 10 carbon atoms. More preferably, it is a vinyl group.
  • the alkynyl group is a group having a triple bond in the alkyl group, and the alkynyl group has 2 to 25 carbon atoms, preferably 2 to 10 carbon atoms. More preferred is an ethynyl group.
  • cycloalkyl group examples include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, and the like. Among these, a cyclopentyl group and a cyclohexyl group are preferable.
  • the number of carbon atoms forming the ring of the cycloalkyl group is 3 to 25, preferably 3 to 10, more preferably 3 to 8, and further preferably 3 to 6.
  • the alkoxy group is a group represented by —OY 10 , and examples of Y 10 include the same groups as those described above for the alkyl group and the cycloalkyl group.
  • the number of carbon atoms of the alkoxy group is preferably 1 to 25, more preferably 1 to 10.
  • the alkylthio group is a group represented by —SY 10 , and examples of Y 10 include the same groups as those described above for the alkyl group and the cycloalkyl group.
  • the alkylthio group has 1 to 25 carbon atoms, preferably 1 to 10 carbon atoms.
  • halogen atom examples include fluorine, chlorine, bromine, iodine and the like, preferably a fluorine atom.
  • aryl groups include phenyl, biphenylyl, terphenylyl, naphthyl, acenaphthylenyl, anthryl, benzoanthryl, aceanthryl, phenanthryl, benzo [c] phenanthryl, phenalenyl, fluorenyl, Picenyl group, pentaphenyl group, pyrenyl group, chrysenyl group, benzo [g] chrysenyl group, s-indacenyl group, as-indacenyl group, fluoranthenyl group, benzo [k] fluoranthenyl group, triphenylenyl group, benzo [b ] A triphenylenyl group, a perylenyl group, etc.
  • a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a fluoranthenyl group, and a fluorenyl group are preferable, a phenyl group, a biphenylyl group, and a terphenylyl group are more preferable, and a phenyl group is more preferable.
  • the aryl group has 6-30 ring-forming carbon atoms, preferably 6-24, more preferably 6-20, and even more preferably 6-18.
  • the arylene group is a divalent group Y 21 in which one hydrogen atom or substituent is further removed from the aryl group.
  • the aralkyl group is represented as —Y 11 —Y 20 .
  • Y 11 is a divalent group (an alkylene group or a cycloalkylene group) obtained by further removing one hydrogen atom or substituent from those exemplified as the alkyl group and the cycloalkyl group.
  • Examples of Y 20 include the aryl group.
  • the aryloxy group is represented as —OY 20 and examples of Y 20 include the same as those mentioned as the aryl group.
  • the heteroaryloxy group is represented as —OY 30, and examples of Y 30 include the same as those described below as the heteroaryl group.
  • the arylthio group is represented by —SY 20, and examples of Y 20 include the same as those mentioned as the aryl group.
  • the heteroarylthio group is represented by —SY 30, and examples of Y 30 include the same groups as those described below as the heteroaryl group.
  • the arylcarbonyloxy group is represented by —O— (C ⁇ O) —Y 20, and examples of Y 20 include the same as those mentioned as the aryl group.
  • a substituted carbonyl group having a substituent selected from an alkyl group and an aryl group is represented by — (C ⁇ O) —Y 10 or — (C ⁇ O) —Y 20, and examples of Y 10 include the alkyl group And the same as those mentioned as the cycloalkyl group, and examples of Y 20 include the same as those mentioned as the aryl group.
  • the heterocyclic group includes a heterocyclic group having no aromaticity and an aromatic heterocyclic group having aromaticity (a monoaryl is a heteroaryl group, and a bivalent is a heteroarylene group).
  • heterocyclic group having no aromaticity examples include a ring group having 3 to 30, preferably 3 to 20 ring-forming atoms including a nitrogen atom, an oxygen atom or a sulfur atom.
  • Specific examples of the heterocyclic ring having no aromaticity include aziridine, oxirane, thiirane, azetidine, oxetane, trimethylene sulfide, pyrrolidine, tetrahydrofuran, tetrahydrothiophene, piperidine, tetrahydropyran, tetrahydrothiopyran and the like.
  • heterocyclic group examples include a cyclic group containing a hetero atom such as a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, or a sulfur atom, and the ring-forming atom is selected from the group consisting of a nitrogen atom, an oxygen atom, or a sulfur atom. It is preferable to contain the atoms.
  • a heteroaryl group having aromaticity is preferable.
  • heteroaryl groups include pyrrolyl, furyl, thienyl, pyridyl, imidazopyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, imidazolyl, oxazolyl, thiazolyl, pyrazolyl, isoxazolyl , Isothiazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, tetrazolyl group, indolyl group, isoindolyl group, benzofuranyl group, isobenzofuranyl group, benzothiophenyl group, isobenzothiophenyl group, indolizinyl group, quinolidinyl group, quinolyl group , Isoquinolyl group, cinnolyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl
  • pyridyl group imidazopyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, benzimidazolyl group, dibenzofuranyl group, dibenzothiophenyl group, carbazolyl group, aryl group or heterocyclic group at the 9-position
  • a substituted carbazolyl group, phenanthrolinyl group and quinazolinyl group are preferred.
  • the number of ring-forming atoms of the heterocyclic group is from 3 to 30, preferably from 5 to 24, more preferably from 5 to 18.
  • the number of ring-forming atoms of the heteroaryl group is 5 to 30, preferably 5 to 24, more preferably 5 to 18.
  • the ring-forming atom other than the carbon atom of the heteroaryl group is preferably a nitrogen atom, an oxygen atom or a sulfur atom.
  • the heteroarylene group is a divalent group Y 31 in which one hydrogen atom or substituent is further removed from the heteroaryl group.
  • the heterocyclic group may be a group derived from a partial structure represented by the following general formulas (XY-1) to (XY-18), for example.
  • X A and Y A are each independently a hetero atom, and an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, or a germanium atom Is preferred.
  • the partial structures represented by the general formulas (XY-1) to (XY-18) have a bond at an arbitrary position to be a heterocyclic group, and this heterocyclic group has a substituent. Also good.
  • the substituted or unsubstituted carbazolyl group may include a group further condensed with a carbazole ring as represented by the following formula, for example. Such a group may also have a substituent. Also, the position of the joint can be changed as appropriate.
  • the mono-substituted amino group having a substituent selected from an alkyl group and an aryl group is represented by —NH (Y 10 ) or —NH (Y 20 ), and Y 10 and Y 20 are as described above.
  • the disubstituted amino group having a substituent selected from an alkyl group and an aryl group is represented by —N (Y 10 ) 2 , —N (Y 20 ) 2 or —N (Y 10 ) (Y 20 ), and Y 10 And Y 20 are as described above.
  • two Y 10 or Y 20 are present, they may be the same as or different from each other.
  • the mono-substituted silyl group having a substituent selected from an alkyl group and an aryl group is represented by —SiH 2 (Y 10 ) or —SiH 2 (Y 20 ).
  • the disubstituted silyl group having a substituent selected from an alkyl group and an aryl group is represented by —SiH (Y 10 ) 2 , —SiH (Y 20 ) 2 or —SiH (Y 10 ) (Y 20 ).
  • the tri-substituted silyl group having a substituent selected from an alkyl group and an aryl group is -Si (Y 10 ) 3 , -Si (Y 20 ) 3 , -Si (Y 10 ) 2 (Y 20 ) or -Si (Y 10 ) (Y 20 ) 2 .
  • Y 10 and Y 20 are as described above, and when there are a plurality of Y 10 or Y 20 s , they may be the same as or different from each other.
  • the substituted sulfonyl group having a substituent selected from an alkyl group and an aryl group is represented by —S ( ⁇ O) 2 —Y 10 or —S ( ⁇ O) 2 —Y 20 , and Y 10 and Y 20 are the above-mentioned Street.
  • Y 10 and Y 20 are as described above, and when two Y 10 or Y 20 are present, they may be the same as or different from each other.
  • the alkylsulfonyloxy group having an alkyl group is represented by —O—S ( ⁇ O) 2 (Y 10 ), and Y 10 is as described above.
  • the arylsulfonyloxy group having a substituent selected from an aryl group is represented by —O—S ( ⁇ O) 2 (Y 20 ), and Y 20 is as described above.
  • the substituent in the case of “substituted or unsubstituted” includes an aryl group having 6 to 30 ring carbon atoms, a heteroaryl group having 5 to 30 ring atoms, and an alkyl group having 1 to 25 carbon atoms.
  • the substituent in the case of “substituted or unsubstituted” includes an aryl group having 6 to 30 ring carbon atoms, a heteroaryl group having 5 to 30 ring atoms, and an alkyl group having 1 to 25 carbon atoms.
  • Preferred is at least one group selected from the group consisting of a group (straight chain or branched alkyl group), an alkylsilyl group having 3 to 25 carbon atoms, an arylsilyl group having 6 to 30 ring carbon atoms, and a cyano group.
  • specific substituents that are preferable in the description of each substituent are preferable.
  • the substituent in the case of “substituted or unsubstituted” is an aryl group having 6 to 30 ring carbon atoms, a heteroaryl group having 5 to 30 ring atoms, or an alkyl group having 1 to 25 carbon atoms.
  • the substituent further substituted on the substituent in the case of “substituted or unsubstituted” includes an aryl group having 6 to 30 ring carbon atoms, a heteroaryl group having 5 to 30 ring atoms, It is preferably at least one group selected from the group consisting of an alkyl group having 1 to 25 carbon atoms (straight chain or branched chain alkyl group), a halogen atom, and a cyano group. More preferably, it is at least one group selected from the specific substituents described above.
  • An electronic device which is one embodiment of the present invention includes the organic electroluminescence element which is one embodiment of the present invention.
  • the organic electroluminescent element which is one embodiment of the present invention can be used for various electronic devices.
  • the organic electroluminescence element which is one embodiment of the present invention can be used for a planar light emitter, a backlight, a light source such as an instrument, a display board, a marker lamp, and the like.
  • the flat light emitter include a flat panel display of a wall-mounted television.
  • the backlight include backlights such as copying machines, printers, and liquid crystal displays.
  • the compound of this invention can be used not only in an organic EL element but in fields, such as an electrophotographic photoreceptor, a photoelectric conversion element, a solar cell, an image sensor.
  • the mode in which the composition is included in the light emitting layer is described as an example.
  • the organic EL element of the aspect by which the composition is contained in one layer of organic layers other than a light emitting layer is mentioned, for example.
  • an anode, a cathode, a light-emitting layer included between the anode and the cathode, and an electron transport zone included between the light-emitting layer and the cathode is illustrated.
  • the light emitting layer is not limited to one layer, and a plurality of light emitting layers may be stacked.
  • the organic EL element has a plurality of light emitting layers, it is sufficient that at least one light emitting layer satisfies the conditions described in the above embodiment.
  • the other light-emitting layer may be a fluorescent light-emitting layer or a phosphorescent light-emitting layer that utilizes light emission by electron transition from a triplet excited state to a direct ground state.
  • these light emitting layers may be provided adjacent to each other, or a so-called tandem organic material in which a plurality of light emitting units are stacked via an intermediate layer. It may be an EL element.
  • a barrier layer may be provided adjacent to at least one of the anode side and the cathode side of the light emitting layer.
  • the barrier layer is preferably disposed in contact with the light emitting layer and blocks at least one of holes, electrons, and excitons.
  • the barrier layer transports electrons, and holes reach a layer on the cathode side of the barrier layer (for example, an electron transport layer).
  • an organic EL element contains an electron carrying layer, it is preferable to contain the said barrier layer between a light emitting layer and an electron carrying layer.
  • the barrier layer transports holes, and the electrons are directed to a layer on the anode side of the barrier layer (for example, a hole transport layer). Stop reaching.
  • the organic EL element includes a hole transport layer
  • a barrier layer may be provided adjacent to the light emitting layer so that excitation energy does not leak from the light emitting layer to the peripheral layer. The excitons generated in the light emitting layer are prevented from moving to a layer (for example, an electron transport layer or a hole transport layer) closer to the electrode than the barrier layer.
  • the light emitting layer and the barrier layer are preferably joined.
  • reaction solution was extracted with toluene, the organic layer was washed with water, dehydrated with magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography to obtain 745 g of 3-bromo-5-chlorobenzaldehyde.
  • DMF is an abbreviation for N, N-dimethylformamide.
  • the crucible, the crucible filled with compound ET-1, and the crucible filled with 8-quinolinolatolithium (Liq) were set in a vacuum deposition apparatus.
  • a glass substrate manufactured by Geomat Co.
  • an ITO transparent electrode anode
  • the film thickness of ITO was 130 nm.
  • Compound HAT was vapor-deposited to form a HAT film having a thickness of 10 nm to form a hole injection layer.
  • a compound HT-1 was vapor-deposited on the hole injection layer to form a 110 nm-thick HT-1 film, thereby forming a first hole transport layer.
  • a compound HT-2 was vapor-deposited on the first hole transport layer to form an HT-2 film having a thickness of 35 nm, thereby forming a second hole transport layer.
  • a mixture of compound PGH-P1 and compound PGH-N1 and compound PGD-1 were formed on the second hole transport layer by co-evaporation to form a light-emitting layer having a thickness of 40 nm.
  • the concentration of the compound PGD-1 contained in the light emitting layer was 5% by mass.
  • the compound ET-1 and 8-quinolinolatolithium (Liq) were formed by co-evaporation at a mass ratio of 50:50 to form an electron transport layer having a thickness of 30 nm. . Liq was vapor-deposited on this electron transport layer to form an electron injection layer having a thickness of 1 nm. Metal Al was vapor-deposited on the electron injection layer to form a metal cathode having a thickness of 80 nm. The organic EL device produced in this way was used as an organic EL device in the initial stage of vapor deposition.
  • the ITO substrate is retracted out of the chamber, and the mixture of the compound PGH-P1 and the compound PGH-N1 is evaporated to a mass of 0.4 g (the remaining amount is 20% by mass). ) Continued until. Thereafter, the ITO substrate is returned to the chamber, and the already prepared organic EL element part is protected with a mask, and then the compound HAT is vapor deposited so as to cover the transparent electrode on the surface on which the transparent electrode line is formed. A HAT film having a thickness of 10 nm was formed to form a hole injection layer.
  • a compound HT-1 was vapor-deposited on the hole injection layer to form a 110 nm-thick HT-1 film, thereby forming a first hole transport layer.
  • a compound HT-2 was vapor-deposited on the first hole transport layer to form an HT-2 film having a thickness of 35 nm, thereby forming a second hole transport layer.
  • a mixture of compound PGH-P1 and compound PGH-N1 and compound PGD-1 were formed on the second hole transport layer by co-evaporation to form a light-emitting layer having a thickness of 40 nm.
  • the concentration of the compound PGD-1 contained in the light emitting layer was 5% by mass.
  • the compound ET-1 and 8-quinolinolatolithium (Liq) were formed by co-evaporation at a mass ratio of 50:50 to form an electron transport layer having a thickness of 30 nm. . Liq was vapor-deposited on this electron transport layer to form an electron injection layer having a thickness of 1 nm. Metal Al was vapor-deposited on the electron injection layer to form a metal cathode having a thickness of 80 nm. The organic EL device produced in this way was used as the organic EL device at the end of vapor deposition.
  • the residue in the crucible is taken out from the vapor deposition apparatus, the residue in the crucible is dissolved in tetrahydrofuran, and the ratio (residue ratio) of compound PGH-P1 and compound PGH-N1 from the peak area values of each component detected by HPLC Asked.
  • Table 1 shows the ratio (initial ratio) of the compound PGH-P1 and the compound PGH-N1 in the crucible in the initial stage (before deposition), and the ratio of the compound PGH-P1 and the compound PGH-N1 in the crucible after deposition ( Residue ratio).
  • Example 2 Example 2 was carried out in the same manner as Example 1 except that compound PGH-N2 was used instead of compound PGH-N1 in the light emitting layer of Example 1.
  • Table 1 shows the ratio (initial ratio) of compound PGH-P1 and compound PGH-N2 in the initial (before vapor deposition) crucible, and the ratio of compound PGH-P1 and compound PGH-N2 in the crucible after vapor deposition ( Residue ratio).
  • Example 3 Example 3 was carried out in the same manner as Example 1 except that compound PGH-N3 was used instead of compound PGH-N1 in the light emitting layer of Example 1.
  • Table 1 shows the ratio (initial ratio) of compound PGH-P1 and compound PGH-N3 in the initial (before vapor deposition) crucible, and the ratio of compound PGH-P1 and compound PGH-N3 in the crucible after vapor deposition ( Residue ratio).
  • Comparative Example 1 uses Compound PGH-C1 instead of Compound PGH-P1 in the light emitting layer of Example 1, and uses Compound PGH-C2 instead of Compound PGH-N1 in the light emitting layer of Example 1. This was carried out in the same manner as in Example 1 except that.
  • Table 1 shows the ratio (initial ratio) of compound PGH-C1 and compound PGH-C2 in the initial (before vapor deposition) crucible, and the ratio of compound PGH-C1 and compound PGH-C2 in the crucible after vapor deposition ( Residue ratio).
  • the mass ratio (film ratio) of the compound PGH-P1 and the compound PGH-N1 in the light emitting layer was analyzed by HPLC.
  • the compound PGH-P1: the compound PGH- N1 5: 5.
  • the mass ratio (film ratio) between the compound PGH-P1 and the compound PGH-N2 in the light emitting layer was analyzed by HPLC.
  • the compound PGH-P1: the compound PGH- N2 5: 5.
  • the mass ratio (film ratio) between the compound PGH-P1 and the compound PGH-N3 in the light emitting layer was analyzed by HPLC.
  • the compound PGH-P1: the compound PGH- N3 5: 5.
  • the mass ratio (film ratio) between the first compound and the second compound in the light emitting layer was the first (before vapor deposition) in the first crucible in the crucible. The ratio was the same as the mass ratio (initial ratio) between the compound and the second compound.
  • the mass ratio (film ratio) of the compound PGH-C1 and the compound PGH-C2 in the light emitting layer was the compound PGH in the crucible at the initial stage (before vapor deposition). The mass ratio (initial ratio) of -C1 and compound PGH-C2 was significantly different.
  • V The voltage (unit: V) when energized between the ITO transparent electrode and the metal Al cathode was measured so that the current density was 10 mA / cm 2 .
  • External quantum efficiency EQE A spectral radiance spectrum when a voltage was applied to the device so that the current density was 10 mA / cm 2 was measured with a spectral radiance meter CS-1000 (manufactured by Konica Minolta). The external quantum efficiency EQE (unit:%) was calculated from the obtained spectral radiance spectrum, assuming that Lambtian radiation was performed.
  • Lifetime LT97 A DC continuous energization test was performed with the initial current density set to 10 mA / cm 2 , the time when the luminance decreased to 97% with respect to the luminance at the start of the test was measured, and the measured time was determined as the lifetime LT97 ( Unit: hours (hrs)).
  • SYMBOLS 1 Organic EL element, 3 ... Anode, 4 ... Cathode, 5 ... Light emitting layer, 7 ... Hole transport layer, 8 ... Electron transport layer.

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  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne une composition dans laquelle deux sortes de composé ou plus sont mélangées, et qui comprend au moins un premier composé représenté par la formule générale (1), et un second composé représenté par la formule générale (2). Dans la formule générale (1), Ｒ１ à Ｒ４, Ａ１ et Ａ２ contiennent au total six structures cycliques représentées par la formule générale (1a). Dans la formule générale (2), Ａ３ et/ouＡ４ est un substituant représenté par la formule générale (2a), l'autre étant un substituant représenté par la formule générale (2b).
PCT/JP2017/046297 2016-12-26 2017-12-25 Composition, matériau pour élément électroluminescent organique, film de composition, élément électroluminescent organique, et appareil électronique WO2018123924A1 (fr)

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JP2021168421A (ja) * 2018-10-10 2021-10-21 株式会社半導体エネルギー研究所 発光デバイス
CN114105743A (zh) * 2021-11-02 2022-03-01 阜阳欣奕华材料科技有限公司 一种合成3-溴-5-氯苯甲醛的方法
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CN114105743A (zh) * 2021-11-02 2022-03-01 阜阳欣奕华材料科技有限公司 一种合成3-溴-5-氯苯甲醛的方法

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