WO2022138790A1 - Composition pour former une couche luminescente d'un élément électroluminescent organique, élément électroluminescent organique, dispositif d'affichage électroluminescent organique et dispositif d'éclairage électroluminescent organique - Google Patents

Composition pour former une couche luminescente d'un élément électroluminescent organique, élément électroluminescent organique, dispositif d'affichage électroluminescent organique et dispositif d'éclairage électroluminescent organique Download PDF

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WO2022138790A1
WO2022138790A1 PCT/JP2021/047764 JP2021047764W WO2022138790A1 WO 2022138790 A1 WO2022138790 A1 WO 2022138790A1 JP 2021047764 W JP2021047764 W JP 2021047764W WO 2022138790 A1 WO2022138790 A1 WO 2022138790A1
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substituent
ring
formula
carbon atoms
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一毅 岡部
宏一朗 飯田
英司 小松
敏光 中井
繁樹 服部
和弘 長山
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三菱ケミカル株式会社
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Priority to JP2022571601A priority patent/JPWO2022138790A1/ja
Priority to KR1020237020109A priority patent/KR20230124575A/ko
Publication of WO2022138790A1 publication Critical patent/WO2022138790A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/658—Organoboranes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
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    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements
    • H—ELECTRICITY
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    • 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
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    • 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
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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    • 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
    • H—ELECTRICITY
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    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
    • H10K59/10—OLED displays
    • H10K59/17—Passive-matrix OLED displays

Definitions

  • the present invention relates to a composition for forming a light emitting layer of an organic electroluminescent element, and an organic electroluminescent element, an organic EL display device, and an organic EL lighting using the composition.
  • OLED organic electroluminescent device
  • An organic electroluminescent device usually has a hole injection layer, a hole transport layer, an organic light emitting layer, an electron transport layer, etc. between an anode and a cathode, and materials suitable for each of these layers are being developed. Yes, the emission colors are red, green, and blue, and development is progressing for each.
  • the vacuum vapor deposition method is easy to stack, it has the advantages of improving charge injection from the anode and / or cathode and facilitating containment of excitons in the light emitting layer.
  • the wet film forming method does not require a vacuum process, it is easy to increase the area, and by using a coating liquid in which a plurality of materials having various functions are mixed, a plurality of materials having various functions can be easily obtained.
  • advantages such as being able to form a layer containing the above materials. Therefore, in recent years, research and development of an organic electroluminescent device by a wet film forming method has been energetically carried out.
  • Patent Documents 1 to 5 study an organic electroluminescent element that forms a light emitting layer containing a light emitting material having a polycyclic heterocyclic compound skeleton containing boron and nitrogen by a wet film forming method. However, it is desired to further extend the drive life of the device. Further, it is desired to reduce the voltage drive of the element and improve the luminous efficiency.
  • An object of the present invention is to provide an organic electroluminescent device which has a light emitting layer containing a polycyclic heterocyclic compound containing boron, exhibits excellent device characteristics, and has a particularly long drive life.
  • the present invention also provides an organic electroluminescent device which has a light emitting layer containing a polycyclic heterocyclic compound containing boron, exhibits excellent element characteristics, is driven at a low voltage, has high luminous efficiency, and has a long driving life. The task is to do.
  • the gist of the present invention is as follows [1] to [23].
  • Rings a, b, and c are independently aromatic hydrocarbon rings that may have substituents or aromatic heterocycles that may have substituents.
  • Y is independently O, NR, or S, respectively.
  • R is an aromatic hydrocarbon ring group which may have a substituent, an aromatic heterocyclic group which may have a substituent, or an alkyl group.
  • the R is a carbon atom adjacent to an atom bonded to Y in at least one ring selected from the group consisting of the ring a, the ring b, and the ring c, and —O—, —S—, ⁇ . It may be bound by C (-R a ) 2- or a single bond.
  • Ra is a hydrogen atom or an alkyl group.
  • the adjacent carbon atom is not a carbon atom constituting the central fused bicyclic structure of the formula (1) containing B and Y. At least one hydrogen atom in the polycyclic heterocyclic compound represented by the formula (1) may be substituted with a halogen atom or deuterium.
  • Compound I Compound represented by the following formula (20)
  • Compound II Compound represented by the following formula (200)
  • Compound III Compound represented by the following formula (210), compound represented by the following formula (220) And one or more compounds selected from the compounds represented by the following formula (230)
  • Compound IV Compounds represented by the following formula (240)
  • Ar 21 to Ar 35 each independently have a hydrogen atom, a benzene ring structure which may have a substituent, or 2 to 10 benzene ring structures which may have a substituent, and are not. Represents a branched or branched and connected structure.
  • W represents CH or N independently, and at least one W is N.
  • Xa 1 , Ya 1 , and Za 1 each independently have a divalent aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, or a carbon which may have a substituent.
  • Each of Xa 2 , Ya 2 and Za 2 independently has a hydrogen atom, an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, or a carbon number which may have a substituent.
  • Represents 3 to 30 aromatic heterocyclic groups g11, h11, and j11 each independently represent an integer of 0 to 6.
  • At least one of g11, h11, and j11 is an integer of 1 or more.
  • a plurality of Xa 1s may be the same or different.
  • a plurality of Ya 1s may be the same or different.
  • a plurality of Za 1s existing may be the same or different.
  • R 31 represents a hydrogen atom or substituent, and the four R 31s may be the same or different.
  • the corresponding Xa 2 , Ya 2 , and Za 2 are not hydrogen atoms, respectively.
  • Ar 41 , Ar 42 , and Ar 43 are each independently an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, and an aromatic having 3 to 30 carbon atoms which may have a substituent.
  • R 21 , R 22 and R 23 each independently represent a hydrogen atom or a substituent.
  • X 21 and X 22 independently represent O, S, or N-Ar 44 , respectively.
  • Ar 44 contains an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, an aromatic heterocyclic group having 3 to 30 carbon atoms which may have a substituent, or a substituent. Two to five structures selected from an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have and an aromatic heterocyclic group having 3 to 30 carbon atoms which may have a substituent are linked. Represents a monovalent group n21, n22, and n23 independently represent 1 or 2, respectively. n24 represents an integer from 1 to 4 and represents When n24 is 2 or more, the plurality of R 21s may be the same or different. )
  • Ar 611 and Ar 612 each independently represent a divalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent.
  • R 611 and R 612 are monovalent aromatic hydrocarbon groups having 6 to 50 carbon atoms, which may independently have a deuterium atom, a halogen atom, or a substituent.
  • G represents a divalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a single bond or a substituent.
  • n 611 and n 612 are each independently an integer of 0 to 4.
  • At least one of Ar 22 , Ar 23 , Ar 24 , Ar 27 , Ar 28 , Ar 29 , Ar 32 , Ar 33 and Ar 34 is the following formula (21) or the following formula.
  • Ar 36 to Ar 39 each independently have a hydrogen atom, a benzene ring structure which may have a substituent, or a benzene ring structure which may have a substituent 2 to 2. Represents a structure of eight, non-branched or branched and connected.
  • the structure represented by the above formula (21) is represented by the following formula (21-1), (21-2), (21-3), (21-4), or (21-5). It is a structure, and the structure represented by the above formula (22) is a structure represented by the following formula (22-1), (22-2), (22-3) or (22-4).
  • Ar 41 , Ar 42 , and Ar 43 in the formula (210), the formula (220), and the formula (230) are represented by any of the following formulas (20-1) to (20-13).
  • Ar 45 contains an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, an aromatic heterocyclic group having 3 to 30 carbon atoms which may have a substituent, or a substituent. Two to five structures selected from an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have and an aromatic heterocyclic group having 3 to 30 carbon atoms which may have a substituent are linked. It is a monovalent group. )
  • a method for manufacturing an organic electroluminescent device which comprises a step of applying and drying the composition for forming a light emitting layer of the organic electroluminescent device according to any one of [1] to [9] to form a light emitting layer.
  • a method for manufacturing an organic EL display device which comprises the method for manufacturing an organic electroluminescent device according to [10].
  • a method for manufacturing an organic EL lighting including the method for manufacturing an organic electroluminescent element according to [10].
  • It has an anode, a cathode, and a light emitting layer provided between the anode and the cathode, and the light emitting layer includes a polycyclic heterocyclic compound represented by the following formula (1), the following compound I, and the following compound.
  • An organic electroluminescent device comprising II, the following compound III, and at least one of the following compounds IV.
  • Rings a, b, and c are independently aromatic hydrocarbon rings that may have substituents or aromatic heterocycles that may have substituents.
  • Y is independently O, NR, or S, respectively.
  • R is an aromatic hydrocarbon ring group which may have a substituent, an aromatic heterocyclic group which may have a substituent, or an alkyl group.
  • the R is a carbon atom adjacent to an atom bonded to Y in at least one ring selected from the group consisting of the ring a, the ring b, and the ring c, and —O—, —S—, ⁇ . It may be bound by C (-R a ) 2- or a single bond.
  • Ra is a hydrogen atom or an alkyl group.
  • the adjacent carbon atom is not a carbon atom constituting the central fused bicyclic structure of the formula (1) containing B and Y. At least one hydrogen atom in the polycyclic heterocyclic compound represented by the formula (1) may be substituted with a halogen atom or deuterium.
  • Compound I Compound represented by the following formula (20)
  • Compound II Compound represented by the following formula (200)
  • Compound III Compound represented by the following formula (210), compound represented by the following formula (220) And one or more compounds selected from the compounds represented by the following formula (230)
  • Compound IV Compounds represented by the following formula (240)
  • Ar 21 to Ar 35 each independently have a hydrogen atom, a benzene ring structure which may have a substituent, or 2 to 10 benzene ring structures which may have a substituent, and are not. Represents a branched or branched and connected structure.
  • W represents CH or N independently, and at least one W is N.
  • Xa 1 , Ya 1 , and Za 1 each independently have a divalent aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, or a carbon which may have a substituent.
  • Each of Xa 2 , Ya 2 and Za 2 independently has a hydrogen atom, an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, or a carbon number which may have a substituent.
  • Represents 3 to 30 aromatic heterocyclic groups g11, h11, and j11 each independently represent an integer of 0 to 6.
  • At least one of g11, h11, and j11 is an integer of 1 or more.
  • a plurality of Xa 1s may be the same or different.
  • a plurality of Ya 1s may be the same or different.
  • a plurality of Za 1s existing may be the same or different.
  • R 31 represents a hydrogen atom or substituent, and the four R 31s may be the same or different.
  • the corresponding Xa 2 , Ya 2 , and Za 2 are not hydrogen atoms, respectively.
  • Ar 41 , Ar 42 , and Ar 43 are each independently an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, and an aromatic having 3 to 30 carbon atoms which may have a substituent.
  • R 21 , R 22 and R 23 each independently represent a hydrogen atom or a substituent.
  • X 21 and X 22 independently represent O, S, or N-Ar 44 , respectively.
  • Ar 44 contains an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, an aromatic heterocyclic group having 3 to 30 carbon atoms which may have a substituent, or a substituent. Two to five structures selected from an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have and an aromatic heterocyclic group having 3 to 30 carbon atoms which may have a substituent are linked. Represents a monovalent group n21, n22, and n23 independently represent 1 or 2, respectively. n24 represents an integer from 1 to 4 and represents When n24 is 2 or more, the plurality of R 21s may be the same or different. )
  • Ar 611 and Ar 612 each independently represent a divalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent.
  • R 611 and R 612 are monovalent aromatic hydrocarbon groups having 6 to 50 carbon atoms, which may independently have a deuterium atom, a halogen atom, or a substituent.
  • G represents a divalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a single bond or a substituent.
  • n 611 and n 612 are each independently an integer of 0 to 4.
  • At least one of Ar 22 , Ar 23 , Ar 24 , Ar 27 , Ar 28 , Ar 29 , Ar 32 , Ar 33 , and Ar 34 is the following formula (21) or the following formula (22). ), The organic electroluminescent device according to [13] or [14].
  • Ar 36 to Ar 39 each independently have a hydrogen atom, a benzene ring structure which may have a substituent, or a benzene ring structure which may have a substituent 2 to 2. Represents a structure of eight, non-branched or branched and connected.
  • the structure represented by the above formula (21) is represented by the following formula (21-1), (21-2), (21-3), (21-4) or (21-5).
  • the structure represented by the above formula (22) is a structure represented by the following formula (22-1), (22-2), (22-3) or (22-4), [ 15] The organic electroluminescent device according to any one of [17].
  • Ar 41 , Ar 42 , and Ar 43 in the formula (210), the formula (220), and the formula (230) are represented by any of the following formulas (20-1) to (20-13).
  • Ar 45 contains an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, an aromatic heterocyclic group having 3 to 30 carbon atoms which may have a substituent, or a substituent. Two to five structures selected from an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have and an aromatic heterocyclic group having 3 to 30 carbon atoms which may have a substituent are linked. It is a monovalent group. )
  • An organic EL display device including the organic electroluminescent device according to any one of [13] to [21].
  • Organic EL lighting including the organic electroluminescent element according to any one of [13] to [21].
  • the composition for forming a light emitting layer and an organic electroluminescent device of the present invention can provide an organic electroluminescent device that exhibits excellent device characteristics and has a particularly long drive life. Further, the composition for forming a light emitting layer and the organic electroluminescent device of the present invention can provide an organic electroluminescent device which exhibits excellent device characteristics and has particularly high luminous efficiency. Further, the composition for forming a light emitting layer and the organic electroluminescent device of the present invention can provide an organic electroluminescent device which exhibits excellent device characteristics and is particularly effective in lowering the voltage. Further, the composition for forming a light emitting layer and the organic electroluminescent element of the present invention can provide an organic electroluminescent element which exhibits excellent element characteristics, is driven at a low voltage, has high luminous efficiency, and has a long driving life.
  • FIG. 1 is a schematic cross-sectional view showing a structural example of the organic electroluminescent device of the present invention.
  • composition for forming a light emitting layer of the organic electroluminescent element of the present invention the organic electroluminescent element, the organic EL display device including the organic electroluminescent element, and the embodiment of the organic EL lighting including the organic electroluminescent element are described in detail.
  • the following description is an example (representative example) of an embodiment of the present invention, and the present invention is not specified in these contents unless the gist thereof is exceeded.
  • the light emitting layer of the organic electroluminescent device contains at least a material having light emitting properties (light emitting material), and preferably contains one or more host materials.
  • the host material is usually a charge transport material, but a material having a low charge transport property may be blended in order to adjust the charge transport property.
  • the composition for forming a light emitting layer of the organic electroluminescent element of the present invention (hereinafter referred to as "the composition for forming a light emitting layer of the present invention") is a polycyclic heterocycle represented by the following formula (1) as a light emitting material. It contains a compound, and as a host material, it contains at least one of the following compound I, the following compound II, the following compound III, and the following compound IV, and further contains an organic solvent.
  • Rings a, b, and c are independently aromatic hydrocarbon rings that may have substituents or aromatic heterocycles that may have substituents.
  • Y is independently O, NR, or S, respectively.
  • R is an aromatic hydrocarbon ring group which may have a substituent, an aromatic heterocyclic group which may have a substituent, or an alkyl group.
  • the R is a carbon atom adjacent to an atom bonded to Y in at least one ring selected from the group consisting of the ring a, the ring b, and the ring c, and —O—, —S—, ⁇ . It may be bound by C (-R a ) 2- or a single bond.
  • Ra is a hydrogen atom or an alkyl group.
  • the adjacent carbon atom is not a carbon atom constituting the central fused bicyclic structure of the formula (1) containing B and Y. At least one hydrogen atom in the polycyclic heterocyclic compound represented by the formula (1) may be substituted with a halogen atom or deuterium.
  • Compound I Compound represented by the following formula (20)
  • Compound II Compound represented by the following formula (200)
  • Compound III Compound represented by the following formula (210), compound represented by the following formula (220) And one or more compounds selected from the compounds represented by the following formula (230)
  • Compound IV Compounds represented by the following formula (240)
  • Ar 21 to Ar 35 each independently have a hydrogen atom, a benzene ring structure which may have a substituent, or 2 to 10 benzene ring structures which may have a substituent, and are not. Represents a branched or branched and connected structure.
  • W represents CH or N independently, and at least one W is N.
  • Xa 1 , Ya 1 , and Za 1 each independently have a divalent aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, or a carbon which may have a substituent.
  • Each of Xa 2 , Ya 2 and Za 2 independently has a hydrogen atom, an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, or a carbon number which may have a substituent.
  • Represents 3 to 30 aromatic heterocyclic groups g11, h11, and j11 each independently represent an integer of 0 to 6.
  • At least one of g11, h11, and j11 is an integer of 1 or more.
  • a plurality of Xa 1s may be the same or different.
  • a plurality of Ya 1s may be the same or different.
  • a plurality of Za 1s existing may be the same or different.
  • R 31 represents a hydrogen atom or substituent, and the four R 31s may be the same or different.
  • the corresponding Xa 2 , Ya 2 , and Za 2 are not hydrogen atoms, respectively.
  • Ar 41 , Ar 42 , and Ar 43 are each independently an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, and an aromatic having 3 to 30 carbon atoms which may have a substituent.
  • R 21 , R 22 and R 23 each independently represent a hydrogen atom or a substituent.
  • X 21 and X 22 independently represent O, S, or N-Ar 44 , respectively.
  • Ar 44 contains an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, an aromatic heterocyclic group having 3 to 30 carbon atoms which may have a substituent, or a substituent. Two to five structures selected from an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have and an aromatic heterocyclic group having 3 to 30 carbon atoms which may have a substituent are linked. Represents a monovalent group n21, n22, and n23 independently represent 1 or 2, respectively. n24 represents an integer from 1 to 4 and represents When n24 is 2 or more, the plurality of R 21s may be the same or different. )
  • Ar 611 and Ar 612 each independently represent a divalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent.
  • R 611 and R 612 are monovalent aromatic hydrocarbon groups having 6 to 50 carbon atoms, which may independently have a deuterium atom, a halogen atom, or a substituent.
  • G represents a divalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a single bond or a substituent.
  • n 611 and n 612 are each independently an integer of 0 to 4.
  • the polycyclic heterocyclic compound represented by the formula (1) functions as a light emitting material
  • the compound I, the compound II, the compound III, Compound IV functions as a host material.
  • at least one of the above compounds I, II, III and IV may be referred to as "Compounds I-IV" or "first host material”.
  • the composition for forming a light emitting layer of the present invention may be referred to as a "first composition”.
  • the organic electroluminescent element using the composition for forming a light emitting layer of the present invention contains the compound I represented by the above formula (20), which is a compound having a structure in which a large number of benzene rings are linked to the light emitting layer, as a host material. Therefore, it is considered that the transportability of charges in the light emitting layer is appropriately adjusted, deterioration of the polycyclic heterocyclic compound represented by the above formula (1), which is a light emitting material, can be suppressed, and the drive life is extended. Be done. In particular, compound I has the effect of suppressing charge transportability.
  • an anthracene-based host material having high electron transportability represented by the formula (30) described later is used as the second host material, electron transportability in the light emitting layer is prevented so that the light emitting material is not excessively reduced and deteriorated. It is considered that the drive life of the element is extended by suppressing the above.
  • the organic electric field light emitting element using the composition for forming a light emitting layer of the present invention is represented by the above formula (200), which is a compound having a structure in which a 6-membered heteroaromatic ring having nitrogen and a benzene ring are linked to the light emitting layer.
  • the compound II as a host material, the transportability of charges in the light emitting layer is appropriately adjusted, the voltage is lowered, the light emission efficiency is improved, and the polycycle represented by the above formula (1), which is a light emitting material, is obtained. It is considered that the deterioration of the heterocyclic compound can be suppressed and the drive life is extended.
  • the W of the above formula (200) of the compound II has a triazine structure in which all of them are nitrogen atoms
  • the LUMO is relatively deep, has an appropriate electron trapping property in addition to the electron transport property, and excessive electrons are contained in the light emitting material. It is considered that the durability of the light emitting material is improved by not supplying the light emitting material, and as a result, the driving life of the organic electroluminescent element is extended. In particular, it is considered that there is a possibility that electrons enter the empty p-orbital of the boron atom of the polycyclic heterocyclic compound represented by the above formula (1), which is a luminescent material, and the deterioration of the luminescent material may be suppressed.
  • compound II since compound II has an aromatic 6-membered ring having a nitrogen atom in the center, it has high electron transportability. Therefore, when compound II is used as the first host, it is considered that by further using a host material having high hole transportability as the host material, the voltage is lowered, the luminous efficiency is improved, and the drive life is extended. ..
  • Compound III The compound represented by the above formula (210) and the compound represented by the above formula (220) contained in the light emitting layer forming composition of the present invention and the light emitting layer of the organic electric field light emitting element formed by the light emitting layer forming composition are represented by the above formula (220).
  • Compound III which is one of the compounds represented by the above formula (230), is always aromatic at the 3-position of the benzene ring to which two or three phenylene groups bonded to the nitrogen atom of the amine are linked. The rings are bonded.
  • the aromatic ring referred to here is a structure represented by Ar 41 , Ar 42 , Ar 43 or a benzene ring.
  • the number of benzene rings bonded to the nitrogen atom of the amine at the para position becomes 2 or 3, and the appropriate distribution of HOMO improves hole transportability and lowers the voltage, and further in the light emitting layer. It is considered that the balance between electrons and holes is improved, the luminous efficiency is improved, the durability is improved, and the drive life of the element is extended. Further, by having a structure such as Ar 41 , Ar 42 , Ar 43 , etc., it is considered that the voltage is further lowered, the luminous efficiency is improved and the life is extended, and the solubility of the compound in an organic solvent is improved. .. Further, it is considered that the durability is improved by appropriately selecting the structures of Ar 41 , Ar 42 , and Ar 43 .
  • compound III has hole transporting properties and holes from the cathode side layer when the light emitting material directly receives the holes injected from the anode side layer and may deteriorate when it becomes an oxidized state. It is considered that the light emitting material is less likely to be directly oxidized and deterioration is suppressed because it is easy to receive. On the contrary, when the light emitting material directly receives the electrons injected from the cathode side and may deteriorate when it is in a reduced state, holes are rapidly transported from Compound III to the light emitting material, and the light emitting material is recombined to emit light. It is considered that the deterioration of the light emitting material is suppressed by making the light emitting material.
  • compound III is a hole-transporting host having a triphenylamine structure, the voltage can be lowered and the luminous efficiency can be reduced by using compound III as the first host and a material having high electron-transporting properties as the second host material. It is considered that an organic electroluminescent device having a long drive life can be obtained.
  • composition for forming a light emitting layer of the present invention and the organic electroluminescent element formed by the composition for forming a light emitting layer are represented by the above formula (240), which is a compound having a structure having two carbazole rings in the light emitting layer.
  • the compound IV as a host material, the transportability of electric charges in the light emitting layer is appropriately adjusted, the voltage is lowered, the luminous efficiency is improved, and the light emitting material is represented by the above formula (1). It is considered that the deterioration of the ring heterocyclic compound can be suppressed and the drive life is extended.
  • Compound IV has a hole transporting property and easily receives holes from the cathode side layer when the light emitting material directly receives the holes injected from the anode side layer and may deteriorate when it becomes an oxidized state. Therefore, it is considered that the light emitting material is less likely to be directly oxidized and deterioration is suppressed. On the contrary, when the light-emitting material directly receives the electrons injected from the cathode side and is likely to deteriorate when it is in a reduced state, holes are rapidly transported from compound IV to the light-emitting material, and the light-emitting material recombines and emits light. Deterioration is considered to be suppressed.
  • Compound IV has two highly planar carbazole ring structures, holes in the light emitting material of the polycyclic heterocyclic compound represented by the above formula (1), which is a highly planar polycyclic heterocyclic compound. It is thought that transportability will improve. At this time, it is considered that the electron supply to the light emitting material is also promptly performed, so that the light is rapidly recombined to emit light and the deterioration of the light emitting material is suppressed. Therefore, by using Compound IV as the first host and using a material having high electron transportability as the second host material, it is possible to obtain an organic electroluminescent device having a low voltage, improved luminous efficiency, and a long drive life. Is thought to be possible.
  • the composition for forming a light emitting layer of the present invention contains a polycyclic heterocyclic compound represented by the above formula (1).
  • the polycyclic heterocyclic compound represented by the formula (1) is preferably a light emitting material.
  • the ring a, the ring b, and the ring c are each independently an aromatic hydrocarbon ring which may have a substituent or an aromatic heterocycle which may have a substituent.
  • the substituent that the aromatic hydrocarbon ring or aromatic heterocycle may have is preferably a group selected from the following substituent group ⁇ .
  • the aromatic hydrocarbon ring or aromatic heterocycle has a central condensed bicyclic structure in the formula (1) composed of B and Y (hereinafter, may be referred to as "central condensed bicyclic structure"). It is preferable to have a 5-membered ring or a 6-membered ring that shares a bond with, and more preferably to have a 6-membered ring that shares a bond with a centrally condensed bicyclic structure.
  • the "central condensed two-ring structure” is a structure in which two saturated hydrocarbon rings including B and two Y are condensed, which is shown in the center of the formula (1). Specifically, it is a structure in which the ring d and the ring e in the following formula (1') are condensed.
  • a 6-membered ring sharing a bond with the central condensed 2-ring structure means, for example, a case where the ring a is a benzene ring (6-membered ring).
  • the aromatic hydrocarbon ring or aromatic heterocycle (which is ring a) has this 6-membered ring” means that the ring a is formed only by the 6-membered ring or includes the 6-membered ring. As described above, it means that another ring or the like is condensed with this 6-membered ring to form the ring a.
  • ring b "ring c", and "5-membered ring”.
  • aromatic hydrocarbon ring examples include an aromatic hydrocarbon ring having 6 to 30 carbon atoms, and an aromatic hydrocarbon ring having 6 to 16 carbon atoms. Is preferable, an aromatic hydrocarbon ring having 6 to 12 carbon atoms is more preferable, and an aromatic hydrocarbon ring having 6 to 10 carbon atoms is particularly preferable.
  • aromatic hydrocarbon ring examples include a benzene ring which is a monocyclic system, a biphenyl ring which is a bicyclic system, a naphthalene ring which is a fused bicyclic system, and a terphenyl ring (m-terphenyl) which is a tricyclic system.
  • o-terphenyl, p-terphenyl fused tricyclics, ashenafutilene ring, fluorene ring, phenylene ring, phenanthrene ring, fused tetracyclic triphenylene ring, pyrene ring, naphthalene ring, fused pentacyclic system.
  • a certain pyrene ring or pentacene ring is preferable, a benzene ring, a biphenyl ring, a naphthalene ring, a terphenyl ring, or a fluorene ring is more preferable, and a benzene ring is most preferable.
  • aromatic heterocycle examples of the aromatic heterocycle in the ring a, the ring b and the ring c of the formula (1) include an aromatic heterocycle having 2 to 30 carbon atoms, and an aromatic heterocycle having 2 to 25 carbon atoms is preferable.
  • An aromatic heterocycle having 2 to 20 carbon atoms is more preferable, an aromatic heterocycle having 2 to 15 carbon atoms is further preferable, and an aromatic heterocycle having 2 to 10 carbon atoms is particularly preferable.
  • the aromatic heterocycle for example, a heterocycle containing 1 to 5 heteroatoms selected from an oxygen atom, a sulfur atom and a nitrogen atom in addition to a carbon atom as a ring-constituting atom is preferable.
  • aromatic heterocycle examples include a pyrrole ring, an oxazole ring, a thiazole ring, an isothiazole ring, an imidazole ring, a thiathiazole ring, a triazole ring, a pyrazole ring, a pyridine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, and an indole ring.
  • Substituent group ⁇ is a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted diarylamino group, a substituted or unsubstituted diheteroarylamino group, a substituted or substituted group.
  • Unsubstituted aryl heteroarylamino group (amino group having aromatic hydrocarbon group and aromatic heterocyclic group), substituted or unsubstituted alkyl group, substituted or unsubstituted alkoxy group, substituted or unsubstituted aryloxy group , And a halogen atom.
  • the substituent that the group selected from the substituent group ⁇ other than the halogen atom may have is the following substituent group ⁇ .
  • Examples of the aromatic hydrocarbon group or aryl structure in the substituent group ⁇ include the group of the aromatic hydrocarbon ring in the ring a, the ring b and the ring c. The same applies to the specific structure and preferable structure of the aromatic hydrocarbon ring.
  • the aromatic hydrocarbon group in the substituent group ⁇ is preferably a benzene ring.
  • Examples of the aromatic heterocyclic group or heteroaryl structure in the substituent group ⁇ include the group of the aromatic heterocycle in the rings a, b and c. The same applies to the specific structure and preferable structure of the aromatic heterocycle.
  • the aromatic heterocyclic group in the substituent group ⁇ is preferably a triazine ring, a benzimidazole ring, a benzothiazole ring, a pyrimid [5,4-d] pyrimidine ring, or a benzo [1,2-d: 4,5-d]. ] It is a imidazole ring.
  • the alkyl group in the substituent group ⁇ may be either a straight chain or a branched chain, and examples thereof include a linear alkyl group having 1 to 24 carbon atoms or a branched chain alkyl group having 3 to 24 carbon atoms.
  • a linear alkyl group having 1 to 18 carbon atoms or a branched alkyl group having 3 to 18 carbon atoms is preferable, and a linear alkyl group having 1 to 12 carbon atoms or a branched chain chain having 3 to 12 carbon atoms is preferable.
  • alkyl group is more preferable, a linear alkyl group having 1 to 6 carbon atoms or a branched alkyl group having 3 to 6 carbon atoms is further preferable, and a linear alkyl group having 1 to 4 carbon atoms or a fraction having 3 to 4 carbon atoms is preferable. Branch-chain alkyl groups are particularly preferred.
  • alkyl group examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group and an isopentyl group.
  • Examples include a group, an n-octyl group, a tert-octyl group and the like.
  • a part of H of the alkyl group in the substituent group ⁇ may be replaced with F.
  • Examples of the alkoxy group in the substituent group ⁇ include a straight chain having 1 to 24 carbon atoms or an alkoxy group having a branched chain having 3 to 24 carbon atoms.
  • a linear alkoxy group having 1 to 18 carbon atoms or an alkoxy group having a branched chain having 3 to 18 carbon atoms is preferable, and a linear alkoxy group having 1 to 12 carbon atoms or a fraction having 3 to 12 carbon atoms is preferable.
  • Branch-chain alkoxy groups are more preferred, linear alkoxy groups having 1 to 6 carbon atoms or branched-chain alkoxy groups having 3 to 6 carbon atoms are even more preferred, and linear alkoxy groups having 1 to 4 carbon atoms or having 3 carbon atoms. Alkoxy groups of ⁇ 4 branched chains are particularly preferable.
  • alkoxy group examples include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group, a hexyloxy group and a heptyloxy group. , Octyloxy group and the like.
  • halogen atom in the substituent group ⁇ examples include a fluorine atom, a chlorine atom, and a bromine atom.
  • a fluorine atom and a chlorine atom are preferable, and among them, a fluorine atom is more preferable.
  • the substituent group ⁇ comprises an aromatic hydrocarbon group optionally substituted with an aralkyl group, an aromatic heterocyclic group optionally substituted with an aralkyl group, an alkyl group, and a halogen atom.
  • aromatic hydrocarbon group, aromatic heterocyclic group, alkyl group, aralkyl group, and halogen atom in the substituent group ⁇ include the same as those of the substituent group ⁇ , and the preferable structure is also the substituent group ⁇ . The same is true.
  • the substituent group ⁇ may be an aromatic hydrocarbon group optionally substituted with an aralkyl group, an aromatic heterocyclic group optionally substituted with an aralkyl group, an alkyl group, or an aralkyl group.
  • Groups are preferred.
  • an aralkyl group which may be substituted with an aralkyl group an aromatic hydrocarbon group or an aromatic heterocyclic group in the substituent group ⁇ , an aralkyl group having 7 to 30 carbon atoms is preferable.
  • a structure in which a benzene ring is bonded to an alkyl group is preferable.
  • (Y) Y in the formula (1) is O, NR, or S.
  • (R) R is an aromatic hydrocarbon ring group which may have a substituent, an aromatic heterocyclic group or an alkyl group which may have a substituent.
  • the two Ys in the formula (1) may be the same or different from each other, but are preferably the same.
  • the two Ys are preferably NR.
  • Examples of the aromatic hydrocarbon ring group and the aromatic heterocyclic group in R of the formula (1) include the group of the aromatic hydrocarbon ring and the aromatic heterocycle in the rings a, b and c of the formula (1). The basis of is mentioned.
  • Examples of the aromatic hydrocarbon ring group and the aromatic heterocyclic group include an aromatic hydrocarbon ring group having 6 to 10 carbon atoms (for example, a phenyl group and a naphthyl group) and an aromatic heterocyclic group having 2 to 15 carbon atoms. (For example, a carbazolyl group) is preferable.
  • R of the formula (1) is an aromatic hydrocarbon ring group which may have a substituent or an aromatic heterocyclic group which may have a substituent
  • the rings a, b and c of the formula (1) It is a group similar to an aromatic hydrocarbon ring group which may have a substituent in the above or an aromatic heterocyclic group which may have a substituent.
  • Specific structures and preferred structures also include aromatic hydrocarbon ring groups which may have substituents on rings a, b and c of formula (1) or aromatic heterocyclic groups which may have substituents. The same is true.
  • R in the formula (1) is an aromatic hydrocarbon ring group which may have a substituent or an aromatic heterocyclic group which may have a substituent
  • the formula (1) is represented by the following formula (21). Will be done.
  • the formula (1) preferably has a structure represented by the following formula (21).
  • Examples of the alkyl group in R of the formula (1) include the alkyl group in the substituent group ⁇ .
  • the alkyl group an alkyl group having 1 to 4 carbon atoms (for example, a methyl group, an ethyl group, etc.) is particularly preferable.
  • R is a carbon atom adjacent to an atom bonded to Y in at least one ring selected from the group consisting of the ring a, the ring b, and the ring c, and —O—, —S—, —C. (-R a ) 2 -or may be bonded by a single bond.
  • Ra is a hydrogen atom or an alkyl group.
  • alkyl group in Ra examples include the alkyl group in the substituent group ⁇ .
  • the alkyl group is particularly preferably an alkyl group having 1 to 4 carbon atoms, such as a methyl group and an ethyl group.
  • the adjacent carbon atoms are not carbon atoms constituting the central condensed bicyclic structure.
  • at least one hydrogen atom in the polycyclic heterocyclic compound represented by the formula (1) may be substituted with a halogen atom or deuterium.
  • Ring a, ring b, ring c, ring d and ring e are the same as in the above formula (1').
  • the ring f and the ring g are the same as the ring a, the ring b or the ring c in the above formula (1'), and each independently has an aromatic hydrocarbon ring or a substituent which may have a substituent. It is an aromatic heterocycle that may be used.
  • Ring f is a carbon atom adjacent to an atom bonded to N in at least one ring of ring a or ring b, and —O—, —S—, —C (—R a ) 2- or a single bond.
  • Ring g is a carbon atom adjacent to an atom bonded to N in at least one ring of ring a or ring c, and —O—, —S—, —C (—R a ) 2- or a single bond.
  • Ra is a hydrogen atom or an alkyl group.
  • the adjacent carbon atoms are not the carbon atoms constituting the rings d and e including B and N, but At least one hydrogen atom in the polycyclic heterocyclic compound represented by the formula (1) may be substituted with a halogen atom or deuterium.
  • the aromatic hydrocarbon ring group and the aromatic heterocyclic group in the ring f and the ring g include an aromatic hydrocarbon ring group having 6 to 10 carbon atoms (for example, a phenyl group, a naphthyl group, etc.) and a carbon number of 2 to 15 carbon atoms.
  • Aromatic heterocyclic groups eg, carbazolyl groups, etc. are preferred.
  • rings f and g which are aromatic hydrocarbon rings or aromatic heterocycles, may have are the same as those of rings a, b and c, and are preferably from the substituent group ⁇ . It is the group to be selected.
  • Equation (22) The formula (21) preferably has a structure represented by the following formula (22).
  • the ring a, the ring b, the ring c, the ring d and the ring e in the above formula (21) are all benzene ring structures, and the ring a, the ring b, the ring c, the ring d and the ring e are substituted.
  • Ring f is a carbon atom adjacent to an atom bonded to N in at least one ring of ring a or ring b, and —O—, —S—, —C (—R a ) 2- or a single bond.
  • Ring g is a carbon atom adjacent to an atom bonded to N in at least one ring of ring a or ring c, and —O—, —S—, —C (—R a ) 2- or a single bond.
  • Ra is a hydrogen atom or an alkyl group.
  • At least one hydrogen atom in the polycyclic heterocyclic compound represented by the formula (22) may be substituted with a halogen atom or deuterium.
  • the polycyclic heterocyclic compound represented by the formula (22) is the polycyclic heterocyclic compound TD1 represented by the formula (71) described later, or the polycyclic heterocyclic compound represented by the formula (81) described later. It is also preferable that it is TD2.
  • the polycyclic heterocyclic compound represented by the above formula (1) is the polycyclic heterocyclic compound TD1 represented by the formula (71) described later, or the polycyclic complex represented by the formula (81) described later. It is also preferable that it is the ring compound TD2.
  • the polycyclic heterocyclic compound represented by the formula (1) is not particularly limited, and examples thereof include the following compounds.
  • the polycyclic heterocyclic compound represented by the formula (1) is also preferably a polycyclic heterocyclic compound represented by the following formula (71).
  • the polycyclic heterocyclic compound represented by the following formula (71) may be referred to as a polycyclic heterocyclic compound TD1.
  • Each of A 1 to A 7 independently has a hydrogen atom, a fluorine atom, an alkyl group which may have a substituent, a heteroaryl group which is an electron-accepting substituent, a nitro group, a cyano group, or an electron.
  • Each of R 71 to R 78 may independently have a hydrogen atom, an alkyl group which may have a substituent, an aromatic hydrocarbon group which may have a substituent, and a substituent.
  • the dotted line means single bond or no bond.
  • the electron cloud of LUMO is localized and gathered at the position where A 1 to A 7 are bonded to the phenyl group. Therefore, by using at least one selected from A 1 to A 7 as an electron acceptor-type substituent, the electron cloud spreads, the energy level of LUMO is stabilized, and the energy difference between HOMO and LUMO becomes small. .. As a result, the polycyclic heterocyclic compound represented by the above formula (71) can obtain an emission spectrum having a long wavelength.
  • Each of A 1 to A 7 independently has a hydrogen atom, a fluorine atom, an alkyl group which may have a substituent, a heteroaryl group which is an electron-accepting substituent, a nitro group, a cyano group, or an electron. It is an aromatic hydrocarbon group or an aromatic heterocyclic group having a heteroaryl group, a nitro group or a cyano group as substituents having an accepting property.
  • at least one selected from A 1 to A 7 is an electron-accepting substituent, and A 1 to A 7 other than the electron-accepting substituent are independently hydrogen atoms and fluorine, respectively. It is an atom or an alkyl group which may have a substituent.
  • the emission wavelength can be adjusted depending on the number and type of A 1 to A 7 , which is preferable.
  • An electron-accepting substituent is a substituent having a chemical structure that tends to have an excess of electrons by extracting electrons from adjacent chemical structures by chemically bonding.
  • the electron-accepting substituent examples include a substituent such as a heteroaryl group, a nitro group and a cyano group, an aromatic hydrocarbon group having the above substituent, an aromatic heterocyclic group and the like. Of these, a heteroaryl group is preferable from the viewpoint of lengthening the wavelength.
  • a heteroaryl group is an aryl group having at least one atom selected from a nitrogen atom, an oxygen atom, and a sulfur atom.
  • Examples of the heteroaryl group include groups having 1 to 4 rings of polycyclic aromatic heteroaryls containing a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom and the like.
  • the electron acceptor substituent has an absolute value of the value obtained by adding the energy level of HOMO and the energy level of LUMO and dividing by 2 (hereinafter, may be referred to as "absolute value ⁇ ") of 3 eV or more. It is preferably a group that is. When the absolute value ⁇ is 3 eV or more, the electron acceptor property of the substituent is empirically improved.
  • the absolute value ⁇ of the electron acceptor substituent is preferably 3.1 eV or more, more preferably 3.5 eV or more, and even more preferably 4.0 eV or more. Further, although the upper limit of the absolute value ⁇ in the electron acceptor substituent is not particularly set, it is generally 7.0 eV or less.
  • the energy level of HOMO and the energy level of LUMO in the electron accepting substituent are the energy level of the molecular orbital of HOMO and the energy level of the molecular orbital of LUMO obtained as follows. That is, the single bond between the electron-accepting substituent in the formula (71) and the adjacent phenyl group is deleted, and a hydrogen atom is added. Then, if the molecular structure of the obtained electron-accepting substituent is calculated by the molecular orbital calculation software Gaussian16 using the general function: B3LYP and the basic function: 6-31G (d), the structure is optimized by the density general function. good.
  • the electron acceptor substituent is a group represented by the following formula (5), a group represented by the following formula (6), a group represented by the following formula (7), or a group represented by the following formula (8). It is preferably the group represented.
  • R 732 to R 745 are each independently a hydrogen atom, an alkyl group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent.
  • alkyl group examples include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec-butyl group, tert-butyl group, n-hexyl group and n-.
  • alkyl group examples include linear, branched, or cyclic alkyl groups having 1 or more and 24 or less carbon atoms, such as an octyl group, a cyclohexyl group, and a dodecyl group.
  • the aromatic hydrocarbon group examples include an aromatic hydrocarbon group having 6 or more and 60 or less carbon atoms, and specifically, a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, a tetracene ring, and the like.
  • examples thereof include a monovalent group of a 6-membered monocyclic ring or a 2 to 5 fused ring such as a pyrene ring, a benzpyrene ring, a chrysen ring, a triphenylene ring, an acenaften ring, a fluorantene ring, and a fluorene ring.
  • R 732 to R 745 may have can be selected from the substituent group Z2 described later.
  • the electron acceptor substituent is preferably the group represented by the above formula (5) from the viewpoint of lengthening the wavelength and easiness of production by organic synthesis.
  • the group represented by the above formula (5) has a relatively large absolute value ⁇ and has less steric hindrance with the adjacent phenyl group in the above formula (71), so that the adjacent phenyl group and the above formula (5) are used.
  • the twist of the ⁇ plane of the represented group is small, and the effect of lengthening the large emission wavelength can be obtained.
  • the group represented by the above formula (5) can be produced relatively easily in organic synthesis, and even when it is desired to improve the solubility in a solvent, it has a long chain (for example, 4 carbon atoms) in R 732 and R 733 .
  • the above) alkyl group can be introduced relatively easily.
  • an alkyl group which may have a substituent is preferable from the viewpoint of increasing the absolute value ⁇ to facilitate the acquisition of a long wavelength emission wavelength and also from the viewpoint of solubility in a solvent. Further, it is more preferable that at least one selected from R 732 and R 733 is a phenyl group having a tert-butyl group.
  • one selected from R 732 and R 733 is an alkyl group which may have a substituent, and the other is an alkyl group.
  • Aromatic hydrocarbon groups that may have substituents are preferred.
  • the substituent that the aromatic hydrocarbon group may have can be selected from the substituent group Z2.
  • a 1 to A 7 other than the electron-accepting substituent are alkyl groups which may independently have a hydrogen atom, a fluorine atom, or a substituent.
  • alkyl group examples include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec-butyl group, tert-butyl group, n-hexyl group and n-.
  • alkyl group examples include linear, branched, or cyclic alkyl groups having 1 or more and 24 or less carbon atoms, such as an octyl group, a cyclohexyl group, and a dodecyl group.
  • the substituents that A 1 to A 7 may have can be selected from the substituent group Z2 described later.
  • a 1 to A 7 are each independently a fluorine atom or an alkyl group which may have a substituent
  • a 1 to A 7 are hydrogen atoms due to their electron acceptability. Since the emission wavelength is slightly shorter or longer than in the case, it is preferable to select a substituent according to the target wavelength.
  • a 1 to A 7 are each independently long-chain alkyl groups for the purpose of improving the solubility in a solvent.
  • At least one selected from A 1 , A 4 , and A 7 is preferably an electron acceptor-type substituent, and more preferably a group represented by the formula (5).
  • both A 1 and A 7 are electron acceptor substituents, almost the same wavelength lengthening effect can be obtained as compared with the case where only A 4 is the same electron acceptor substituent. Further, it is preferable that two or more selected from A 1 to A 7 are electron acceptor substituents because the wavelength becomes longer, and two or more selected from A 1 to A 7 are electron acceptor property. It is preferable that the substituent is a substituent and at least one of them is an electron acceptor - type substituent because the wavelength is further extended.
  • the single bond connecting the adjacent phenyl groups A 1 to A 7 is twisted, and the ⁇ plane of the adjacent phenyl group and the main aromatic hydrocarbon group of the electron acceptor-type substituent is formed. It is preferable not to twist it. This twist makes it difficult for the charges of the adjacent phenyl group and the electron acceptor-type substituent to be exchanged smoothly, and it becomes difficult for the emission wavelength of the above formula (71) to be lengthened.
  • R 71 to R 78 may independently have a hydrogen atom, an alkyl group which may have a substituent, an aromatic hydrocarbon group which may have a substituent, and a substituent.
  • alkyl group examples include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec-butyl group, tert-butyl group, n-hexyl group and n-.
  • alkyl group examples include linear, branched, or cyclic alkyl groups having 1 or more and 24 or less carbon atoms, such as an octyl group, a cyclohexyl group, and a dodecyl group.
  • the aromatic hydrocarbon group examples include an aromatic hydrocarbon group having 6 or more and 60 or less carbon atoms, and specifically, a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, a tetracene ring, and the like.
  • examples thereof include a monovalent group of a 6-membered monocyclic ring or a 2 to 5 fused ring such as a pyrene ring, a benzpyrene ring, a chrysen ring, a triphenylene ring, an acenaften ring, a fluorentene ring, and a fluorene ring.
  • the aromatic heterocyclic group preferably has an aromatic heterocyclic group having 3 or more and 60 or less carbon atoms, and specifically, a furan ring, a benzofuran ring, a thiophene ring, a benzothiophene ring, a pyrrole ring, a pyrazole ring, or an imidazole ring.
  • Oxadiazole ring indole ring, carbazole ring, pyrrolobymidazole ring, pyrrolopyrazole ring, pyrrolopyrrole ring, thienopyrrole ring, thienothiophene ring, flopyrol ring, furan ring, thienoflan ring, benzoisoxazole ring, benzoisothiazole ring, Benzoimidazole ring, pyridine ring, pyrazine ring, pyridazine ring, pyrimidine ring, triazine ring, quinoline ring, isoquinoline ring, cinnoline ring, quinoxalin ring, phenanthridine ring, benzoimidazole ring, perimidine ring, quinazoline ring, quinazolinone ring, azulene.
  • Examples thereof include monovalent groups of 5- or 6-membered monocyclic rings or 2-
  • R 71 to R 78 may have can be selected from the substituent group Z2 described later.
  • At least one selected from R 71 to R 78 is an electron donor substituent from the viewpoint of lengthening the wavelength.
  • An electron donor substituent is a substituent having a chemical structure that is liable to become electron deficient by donating electrons from adjacent chemical structures by chemically bonding.
  • the electron cloud of HOMO is localized and gathered at R 71 to R 78 . Therefore, by using at least one selected from R 71 to R 78 as an electron donor substituent, the electron cloud of HOMO is likely to spread outward, the energy level of HOMO is destabilized, and HOMO is formed. The energy difference of LUMO becomes small. As a result, the polycyclic heterocyclic compound represented by the above formula (71) can obtain an emission spectrum having a long wavelength.
  • the electron donor substituent is preferably a group having an absolute value ⁇ of less than 3 eV.
  • the absolute value ⁇ is less than 3 eV, the electron donor property of the substituent is empirically improved.
  • the absolute value ⁇ of the electron donor substituent is more preferably less than 2.97 eV, further preferably less than 2.8 eV, and particularly preferably less than 2.6 eV from the viewpoint of lengthening the wavelength. Further, although the lower limit of the absolute value ⁇ in the electron donor substituent is not particularly set, it is generally 1 eV or more.
  • the HOMO energy level and the LUMO energy level in the electron donor substituent are the HOMO molecular orbital energy level and the LUMO molecular orbital energy level obtained as follows. That is, the single bond between the electron donor substituent in the formula (71) and the adjacent phenyl group is deleted, and a hydrogen atom is added. Then, if the molecular structure of the obtained electron donor substituent is calculated by the density general function using the molecular orbital calculation software Gaussian16 using the general function: B3LYP and the basic function: 6-31G (d). good.
  • the electron donor substituent is preferably a group represented by the following formula (2), a group represented by the following formula (3), or a group represented by the following formula (4).
  • Each of R 709 to R 731 is an alkyl group which may have a substituent, an aromatic hydrocarbon group which may have a substituent, or a hydrogen atom, respectively.
  • alkyl group examples include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec-butyl group, tert-butyl group, n-hexyl group and n-.
  • alkyl group examples include linear, branched, or cyclic alkyl groups having 1 or more and 24 or less carbon atoms, such as an octyl group, a cyclohexyl group, and a dodecyl group.
  • the aromatic hydrocarbon group examples include an aromatic hydrocarbon group having 6 or more and 60 or less carbon atoms, and specifically, a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, a tetracene ring, and the like.
  • examples thereof include a monovalent group of a 6-membered monocyclic ring or a 2 to 5 fused ring such as a pyrene ring, a benzpyrene ring, a chrysen ring, a triphenylene ring, an acenaften ring, a fluorantene ring, and a fluorene ring.
  • R 709 to R 731 may have can be selected from the substituent group Z2 described later.
  • the electron donor substituent is preferably the group represented by the above formula (2) from the viewpoint of lengthening the wavelength, ease of production by organic synthesis, and balance of structural stability.
  • the group represented by the above formula (2) has a relatively small absolute value ⁇ , and the effect of lengthening the emission wavelength can be obtained. Further, the group represented by the above formula (2) can be produced relatively easily in organic synthesis, and even when it is desired to improve the solubility in a solvent, a long-chain alkyl group is compared with R 709 to R 716 . It can be easily introduced.
  • At least one selected from R 709 to R 716 is preferably a tert-butyl group from the viewpoint of solubility in a solvent and ease of synthesis.
  • each of R 71 to R 78 independently has an alkyl group which may have a substituent, an aromatic hydrocarbon group which may have a substituent, and an aromatic which may have a substituent.
  • the emission wavelength is slightly shorter or longer than that in the case where R 71 to R 78 are hydrogen atoms due to their electrophilicity. It is preferable to select the substituent according to the wavelength of.
  • R 71 to R 78 are each independently long-chain alkyl groups for the purpose of improving the solubility in a solvent.
  • the dotted line may be a single bond or no bond.
  • the dotted line is preferably a single bond.
  • the electron cloud spreads and the emission wavelength becomes slightly longer.
  • the dotted line is a single bond, it becomes easy to introduce an electron acceptor substituent in A 1 to A 7 and an electron donor substituent in R 71 to R 78 .
  • the polycyclic heterocyclic compound of the above formula (71) is an asymmetric type because it has an effect of narrowing the half width of the emission wavelength. It is considered that the half-value width of the emission spectrum is narrowed because the polycyclic heterocyclic compounds are less likely to associate with each other due to the asymmetric type and the symmetry is lowered, and the interaction between the polycyclic heterocyclic compounds is lowered.
  • the polycyclic heterocyclic compound is an asymmetric type when it is rotated by 180 ° with respect to the axis of rotation when the line connecting the bond axis of B and A4 is used as the axis of rotation in the above equation (71). It does not have the same structure, or it is not mirror-symmetric with respect to a plane perpendicular to the plane formed by the polycyclic heterocycle of the compound of the above formula (71) including the axis of rotation.
  • a 1 and A 7 are different, A 2 and A 6 are different, A 3 and A 5 are different, R 71 and R 78 are different, R 72 and R 77 are different, R 73 .
  • R 76 are different, or R 74 and R 75 are different, the structure.
  • substituent group Z2 examples include the following groups.
  • a linear, branched, or cyclic alkyl group usually having 1 or more carbon atoms, preferably 4 or more carbon atoms, usually 24 or less, preferably 12 or less carbon atoms; for example, a methyl group, an ethyl group, or n-.
  • the number of carbon atoms is usually 2 or more, and usually 24.
  • An alkenyl group which is less than or equal to, preferably 12 or less; for example, a vinyl group or the like.
  • Aalkoxy group for example, a methoxy group, an ethoxy group, etc.
  • the above is usually 24 or less, preferably 12 or less dialkylamino groups; for example, dimethylamino group, diethylamino group, etc., which usually have 10 or more carbon atoms, preferably 12 or more, and usually 36 or less.
  • diarylamino group for example, a diphenylamino group, a ditrilamino group, an N-carbazolyl group, etc., an arylalkylamino group having a carbon number of usually 7 or more, usually 36 or less, preferably 24 or less;
  • an acyl group such as a phenylmethylamino group having a carbon number of usually 2 or more, usually 24 or less, preferably 12 or less; for example, a halogen atom such as an acetyl group or a benzoyl group; for example, a fluorine atom or a chlorine atom.
  • a syroxy group preferably 3 or more, usually 36 or less, preferably 24 or less; for example, a trimethylsiloxy group, a triphenylsiloxy group, etc., which has 6 or more carbon atoms and usually 36 or less, preferably 36 or less.
  • Is 24 or less aromatic hydrocarbon groups for example, phenyl groups
  • Aromatic heterocyclic groups having a carbon number of usually 3 or more, preferably 4 or more, usually 36 or less, preferably 24 or less; for example, a thienyl group, a pyridyl group, etc. having 7 or more carbon atoms.
  • -1-phenylmethyl group 1,1-di (n-hexyl) -1-phenylmethyl group, 1,1-di (n-octyl) -1-phenylmethyl group, phenylmethyl group, phenylethyl group, 3 -Phenyl-1-propyl group, 4-phenyl-1-n-butyl group, 1-methyl-1-phenylethyl group, 5-phenyl-1-n-propyl group, 6-phenyl-1-n-hexyl group , 6-naphthyl-1-n-hexyl group, 7-phenyl-1-n-heptyl group, 8-phenyl-1-n-octyl group, 4-phenylcyclohexyl group, etc.
  • the number of carbon atoms is 2 or more, preferably 4 or more. And 40 or less, preferably 30 or less, more preferably 20 or less heteroaralkyl groups; 1,1-dimethyl-1- (2-pyridyl) methyl group, 1,1-di (n-hexyl) -1-.
  • polycyclic heterocyclic compound TD1 ⁇ Specific example of polycyclic heterocyclic compound TD1>
  • the structure of the polycyclic heterocyclic compound TD1 represented by the formula (71) is not particularly limited, and examples thereof include the following structures.
  • the polycyclic heterocyclic compound represented by the formula (1) is also preferably a polycyclic heterocyclic compound represented by the following formula (81).
  • the polycyclic heterocyclic compound represented by the following formula (81) may be referred to as a polycyclic heterocyclic compound TD2.
  • R 81 and four R 82 each independently have a hydrogen atom, an alkyl group having 10 or less carbon atoms which may have a substituent, and a carbon number which may have a substituent. It represents an aromatic heterocyclic group having 3 or more and 20 or less carbon atoms which may have an aromatic hydrocarbon group of 6 or more and 20 or less or a substituent.
  • a 81 represents a structure represented by the following formula (82). a80, b80, c80, and d80 each independently represent an integer of 0 to 2, and at least one of a80 to d80 is an integer of 1 or more. When there are a plurality of A 81s in the formula (81), the plurality of A 81s may be the same or different.
  • the asterics (*) represent the joint and represent the joint.
  • RF represents a fluoroalkyl group having 5 or less carbon atoms.
  • R 83 may have an alkyl group having 10 or less carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 or more carbon atoms and 20 or less carbon atoms which may have a substituent, or a carbon which may have a substituent.
  • e80 represents an integer from 0 to 5.
  • the two RFs in equation (82) may be the same or different.
  • the plurality of R 83s may be the same or different.
  • the polycyclic heterocyclic compound TD2 represented by the above formula (81) has a condensed heterocyclic skeleton containing a boron atom and a nitrogen atom as a basic skeleton, and the two basic skeletons are represented by the above formula (82). It is characterized in that at least one quaternary carbon atom substituted with a fluoroalkyl group and a benzene ring is connected.
  • the fluorine atom which is a strong electron-withdrawing group, is not directly substituted with the basic skeleton, so that the ionization potential has a great influence on the element characteristics of the organic electric field light emitting element. It is possible to shorten the emission wavelength without significantly changing the electron affinity.
  • the polycyclic heterocyclic compound TD2 is an organic solvent. Excellent solubility in. Therefore, the film produced by the wet film forming method has high uniformity and is suitable as a light emitting material for an organic electroluminescent element.
  • R 81 and R 82 Each of the R 81 and the four R 82s in the formula (81) independently has a hydrogen atom, an alkyl group having 10 or less carbon atoms which may have a substituent, and 6 carbon atoms which may have a substituent. It represents an aromatic heterocyclic group having 3 or more and 20 or less carbon atoms which may have an aromatic hydrocarbon group or a substituent having 20 or less.
  • alkyl groups having 10 or less carbon atoms examples include methyl group, ethyl group, branched, linear or cyclic propyl group, butyl group, pentyl group, hexyl group, octyl group, nonyl group, decyl group and adamantyl group. Can be mentioned.
  • R 1 is an alkyl group having 10 or less carbon atoms, a methyl group, a branched, linear or cyclic propyl group or a butyl group is preferable, and a branched butyl group is particularly preferable, from the viewpoint of the stability of the compound. ..
  • aromatic hydrocarbon groups having 6 or more and 20 or less carbon atoms include monovalent groups such as a benzene ring, a naphthalene ring, a phenanthrene ring, an anthracene ring, a chrysen ring, a pyrene ring, a benzoanthracene ring, and a perylene ring. From the viewpoint of solubility of the compound, a phenyl group, which is a monovalent group of the benzene ring, is preferable.
  • aromatic heterocyclic groups having 3 or more and 20 or less carbon atoms include monovalent groups such as a pyridine ring, a quinoline ring, a benzofuran ring, and a carbazole ring.
  • R 81 a hydrogen atom and an alkyl group having 1 to 4 carbon atoms are preferable, and a hydrogen atom or a t-butyl group is more preferable.
  • a hydrogen atom is preferable as R 82 .
  • a80, b80, c80, and d80 each independently represent an integer of 0 to 2, and at least one of a80 to d80 is an integer of 1 or more. From the viewpoint of the short emission wavelength of the compound, a80 + b80 + c80 + d80 is preferably 2 or more, and a80 + b80 + c80 + d80 is particularly preferably 4 or more.
  • RF represents a fluoroalkyl group having 5 or less carbon atoms.
  • fluoroalkyl groups having 5 or less carbon atoms include perfluoroalkyl groups such as trifluoromethyl group, pentafluoroethyl group, branched, linear or cyclic perfluoropropyl group, perfluorobutyl group and perfluoropentane group. From the viewpoint of the film-forming property of the compound, a trifluoromethyl group and a pentafluoroethyl group are preferable, and a trifluoromethyl group is particularly preferable.
  • R 83 contains an alkyl group having 10 or less carbon atoms which may have a substituent, and an aromatic hydrocarbon group or a substituent having 6 or more and 20 or less carbon atoms which may have a substituent. It represents an aromatic heterocyclic group having 3 or more and 20 or less carbon atoms which may be possessed.
  • the alkyl group having 10 or less carbon atoms include a methyl group, an ethyl group, a branched, linear or cyclic propyl group, a butyl group, a pentyl group, a hexyl group, an octyl group, a nonyl group, and a decyl group.
  • a branched or linear propyl group, butyl group, pentyl group or hexyl group is preferable, and a branched or linear butyl group, branched, linear or cyclic hexyl group is particularly preferable. ..
  • aromatic hydrocarbon groups having 6 or more and 20 or less carbon atoms include monovalent groups such as a benzene ring, a naphthalene ring, a phenanthrene ring, an anthracene ring, a chrysen ring, a pyrene ring, a benzoanthracene ring, and a perylene ring. From the viewpoint of solubility of the compound, a phenyl group, which is a monovalent group of the benzene ring, is preferable.
  • aromatic heterocyclic groups having 3 or more and 20 or less carbon atoms include monovalents such as a pyridine ring, a quinoline ring, a benzofuran ring, and a carbazole ring.
  • R 81 to R 83 may have> R 81 , R 82 , and R 83 have an alkyl group having 10 or less carbon atoms which may have a substituent, and an aromatic hydrocarbon group or a substituent having 6 or more and 20 or less carbon atoms which may have a substituent.
  • an aromatic heterocyclic group having 3 or more and 20 or less carbon atoms which may be possessed examples of the substituent which the alkyl group, the aromatic hydrocarbon group and the aromatic heterocyclic group may have are described later. It can be selected from the substituent group W1.
  • an alkyl group having 10 or less carbon atoms, an aromatic hydrocarbon group or an aromatic heterocyclic group having 20 or less carbon atoms, and an aralkyl group having 30 or less carbon atoms are preferable, and an alkyl group having 10 or less carbon atoms is more preferable.
  • An aromatic hydrocarbon group having 20 or less carbon atoms, and an aralkyl group having 30 or less carbon atoms are preferable, and an alkyl group having 10 or less carbon atoms is more preferable.
  • Examples of an alkyl group having 10 or less carbon atoms as a substituent include a methyl group and an ethyl group, as well as a branched, linear and cyclic propyl group, a butyl group, a pentyl group, a pentyl group, a hexyl group, an octyl group and a nonyl group. , A decyl group. From the viewpoint of the stability of the compound, a methyl group, an ethyl group, a branched group, a linear group, a cyclic propyl group and a butyl group are preferable, and a branched propyl group is particularly preferable.
  • aromatic hydrocarbon groups having 6 or more and 20 or less carbon atoms as substituents include monovalent rings such as benzene ring, naphthalene ring, phenanthren ring, anthracene ring, chrysen ring, pyrene ring, benzoanthracene ring and perylene ring.
  • a group is mentioned, and from the viewpoint of solubility of the compound, a phenyl group which is a monovalent group of a benzene ring is preferable.
  • Examples of the aromatic heterocyclic group having 3 or more carbon atoms and 20 or less carbon atoms as a substituent include a monovalent group such as a pyridine ring, a quinoline ring, a benzofuran ring, and a carbazole ring.
  • Examples of an aralkyl group having 30 or less carbon atoms as a substituent include a benzyl group, a 2-phenylethyl group, a 2-phenylpropyl-2-yl group, a 2-phenylbutyl-2-yl group, and a 3-phenylpentyl-. 3-yl group, 3-phenyl-1-propyl group, 4-phenyl-1-butyl group, 5-phenyl-1-pentyl group, 6-phenyl-1-hexyl group, 7-phenyl-1-heptyl group, Examples thereof include a 8-phenyl-1-octyl group.
  • substituent group W1 examples include the following groups. For example, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec-butyl group, tert-butyl group, n-hexyl group, cyclohexyl group, dodecyl group and the like.
  • a linear, branched, or cyclic alkyl group usually having 1 or more carbon atoms, preferably 4 or more, usually 24 or less, preferably 12 or less;
  • Aralkill group For example, an alkoxy group such as a methoxy group or an ethoxy group having a carbon number of usually 1 or more, usually 24 or less, preferably 12 or less;
  • an alkoxycarbonyl group such as a methoxycarbonyl group or an ethoxycarbonyl group, which usually has 2 or more carbon atoms and usually has 24 or less, preferably 12 or less carbon atoms;
  • the alkyl group, the aromatic hydrocarbon group or the aromatic heterocyclic group is preferable, and the alkyl group and the aromatic hydrocarbon group are more preferable. From the viewpoint of charge transportability, it is more preferable to have no substituent.
  • each substituent of the above-mentioned substituent group W1 may further have a substituent.
  • substituents the same ones as those of the above-mentioned substituents (substituent group W1) can be used.
  • the polycyclic complex compound TD2 represented by the above formula (81) preferably has a structure represented by the following formula (83).
  • R 81 , R 82 , and A 81 are synonymous with R 81 , R 82 , and A 81 in equation (81).
  • a83, b83, c83 and d83 are independently 0 or 1, and at least one is 1.
  • composition for forming a light emitting layer of the present invention may contain only one kind of the polycyclic heterocyclic compound represented by the above formula (1), or may contain two or more kinds.
  • composition for forming a light emitting layer of the present invention contains compound I represented by the following formula (20).
  • Ar 21 to Ar 35 each independently have a hydrogen atom, a benzene ring structure which may have a substituent, or 2 to 10 benzene ring structures which may have a substituent, and are not. Represents a branched or branched and connected structure.
  • Ar 21 to Ar 35 may have a substituent or a benzene ring structure may have a substituent, and 2 to 10 benzene ring structures may be unbranched or branched and linked.
  • the substituent that the benzene ring may have in the above case is preferably an alkyl group.
  • the alkyl group as a substituent is usually 1 or more and 12 or less, preferably 8 or less, more preferably 6 or less, and more preferably 4 or less, linear, branched or cyclic. It is an alkyl group, specifically, a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, a sec-butyl group, a tert-butyl group, and an n-hexyl group. , Cyclohexyl group, 2-ethylhexyl group and the like.
  • Ar 36 to Ar 39 each independently have a hydrogen atom, a benzene ring structure which may have a substituent, or a benzene ring structure which may have a substituent 2 to 2. Represents a structure of eight, non-branched or branched and connected.
  • Ar 36 to Ar 39 may have a substituent or a benzene ring structure may have a substituent, and 2 to 10 benzene ring structures may be unbranched or branched.
  • the substituent that the benzene ring may have in the case of the structure in which the benzene ring is linked is preferably an alkyl group as the substituent.
  • any one of Ar 22 , Ar 23 and Ar 24 , any one of Ar 27 , Ar 28 and Ar 29 , and any one of Ar 32 , Ar 33 and Ar 34 is preferably a structure represented by the formula (21) or the formula (22), and Ar 22 , Ar 27 and Ar 32 are represented by the formula (21) or the formula (22). The structure is more preferable.
  • the structure represented by the above formula (21) is a structure represented by the following formula (21-1), (21-2), (21-3), (21-4) or (21-5).
  • the structure represented by the above formula (22) is preferably a structure represented by the following formulas (22-1), (22-2), (22-3) or (22-4).
  • These structures may be substituted with an alkyl group as the substituent. From the viewpoint of improving solubility, it is preferably substituted with an alkyl group. From the viewpoint of charge transportability and durability when driving the device, it is preferable not to have a substituent.
  • the structure represented by the formula (21) is preferably the structure represented by the formula (21-1), (21-3), (21-4), or (21-5).
  • the structure represented by the formula (22) is more preferably a structure represented by the formula (22-1), and at least one structure represented by the formula (21) or the formula (22). It is particularly preferable to include the structure represented by the formula (21-1) or the structure represented by the formula (22-3).
  • the compound represented by the above formula (20) contains such a structure, so that the transportability of the charge in the light emitting layer can be appropriately adjusted and the luminous efficiency is improved. Further, it is considered that the inclusion of such a structure is excellent in solubility and durability when the element is driven.
  • the compound I represented by the formula (20) is a small molecule material, and the molecular weight is preferably 3,000 or less, more preferably 3,000 or less, particularly preferably 2,000 or less, and most preferably. It is 1,500 or less.
  • the lower limit of the molecular weight of compound I is usually 300 or more, preferably 350 or more, and more preferably 400 or more.
  • the compound I represented by the formula (20) is not particularly limited, and examples thereof include the following compounds.
  • composition for forming a light emitting layer of the present invention may contain only one kind of compound I represented by the above formula (20), or may contain two or more kinds.
  • composition for forming a light emitting layer of the present invention contains compound II represented by the following formula (200).
  • W represents CH or N independently, and at least one W is N.
  • Xa 1 , Ya 1 , and Za 1 each independently have a divalent aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, or a carbon which may have a substituent.
  • Each of Xa 2 , Ya 2 and Za 2 independently has a hydrogen atom, an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, or a carbon number which may have a substituent.
  • Represents 3 to 30 aromatic heterocyclic groups g11, h11, and j11 each independently represent an integer of 0 to 6.
  • At least one of g11, h11, and j11 is an integer of 1 or more.
  • a plurality of Xa 1s may be the same or different.
  • a plurality of Ya 1s may be the same or different.
  • a plurality of Za 1s existing may be the same or different.
  • R 31 represents a hydrogen atom or substituent, and the four R 31s may be the same or different.
  • the corresponding Xa 2 , Ya 2 , and Za 2 are not hydrogen atoms, respectively.
  • the compound II represented by the above formula (200) is preferably a charge transport compound, that is, a charge transport host material.
  • ⁇ W> W in the above formula (200) represents CH or N, and at least one of them is N, but from the viewpoint of electron transportability and electron durability, at least two are preferably N, and all are N. It is more preferable to have.
  • Xa 1 , Ya 1 , Za 1 , Xa 2 , Ya 2 , Za 2 are divalent aromatic hydrocarbon groups having 6 to 30 carbon atoms which may have a substituent, and when Xa 2 and Ya 2 are used.
  • Za 2 is an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent
  • the aromatic hydrocarbon ring of the aromatic hydrocarbon group having 6 to 30 carbon atoms is 6 A monocyclic member ring or a 2-5 fused ring is preferable.
  • benzene ring examples include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a fluorene ring, a perylene ring, a tetracene ring, a pyrene ring, a benzpyrene ring, a chrysene ring, a triphenylene ring, a fluoranthene ring, an indenofluorene ring and the like.
  • a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, or a fluorene ring is preferable, a benzene ring, a naphthalene ring, a phenanthrene ring, or a fluorene ring is more preferable, and a benzene ring, a naphthalene ring, or a fluorene ring is more preferable.
  • Xa 1 , Ya 1 , and Za 1 in the above formula (200) are divalent aromatic heterocyclic groups having 3 to 30 carbon atoms which may have a substituent
  • Za 2 is an aromatic heterocyclic group having 3 to 30 carbon atoms which may have a substituent
  • the aromatic heterocyclic ring of the aromatic heterocyclic group having 3 to 30 carbon atoms is 5 or A 6-membered monocyclic ring or a 2-5 fused ring is preferable.
  • the thiophene ring, pyrrole ring, imidazole ring, pyridine ring, pyrimidine ring, triazine ring, quinoline ring, quinazoline ring, carbazole ring, dibenzofuran ring, dibenzothiophene ring, indolocarbazole ring, phenanthroline ring, or indenocarbazole ring are preferable.
  • a pyridine ring it is more preferably a pyridine ring, a pyrimidine ring, a triazine ring, a quinoline ring, a quinazoline ring, a carbazole ring, a dibenzofuran ring or a dibenzothiophene ring, and more preferably a carbazole ring, a dibenzofuran ring or a dibenzothiophene ring.
  • a particularly preferable aromatic hydrocarbon ring is a benzene ring, a naphthalene ring, or a phenanthrene ring, and a particularly preferable aromatic ring.
  • the heterocycle is a carbazole ring, a dibenzofuran ring or a dibenzothiophene ring.
  • g11, h11, j11> g11, h11, and j11 each independently represent an integer of 0 to 6, and at least one of g11, h11, and j11 is an integer of 1 or more. From the viewpoint of charge transportability and durability, it is preferable that g11 is 2 or more, or at least one of h11 and j11 is 3 or more.
  • the compound represented by the above formula (200) has 8 to 18 rings in total, including a ring having 3 Ws in the center, in terms of charge transportability, durability and organic solvent. It is preferable from the viewpoint of solubility.
  • R 31 is preferably an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent or an aromatic having 3 to 30 carbon atoms which may have a substituent. It is a group heterocyclic group. From the viewpoint of improving durability and charge transportability, it is more preferable to use an aromatic hydrocarbon group which may have a substituent. When there are a plurality of R 31s as substituents, they may be different from each other.
  • the substituent which may be possessed by the above can be selected from the following substituent group Z.
  • the substituent group Z includes an alkyl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkoxycarbonyl group, a dialkylamino group, a diarylamino group, an arylalkylamino group, an acyl group, a halogen atom, a haloalkyl group and an alkylthio group. It is a group consisting of an arylthio group, a silyl group, a siloxy group, a cyano group, an aromatic hydrocarbon group, and an aromatic heterocyclic group. These substituents may contain any of linear, branched and cyclic structures.
  • the substituent group Z has the following structure.
  • an alkoxy group such as a methoxy group or an ethoxy group having a carbon number of usually 1 or more, usually 24 or less, and preferably 12 or less;
  • an aryloxy group or a heteroaryloxy having a phenoxy group, a naphthoxy group, a pyridyloxy group, etc. having a carbon number of usually 4 or more, preferably 5 or more, usually 36 or less, and preferably 24 or less.
  • an alkoxycarbonyl group such as a methoxycarbonyl group or an ethoxycarbonyl group, which usually has 2 or more carbon atoms, usually 24 or less, and preferably 12 or less carbon atoms
  • a dialkylamino group having a carbon number of usually 2 or more, usually 24 or less, preferably 12 or less, such as a dimethylamino group and a diethylamino group
  • an acyl group such as an acetyl group or a benzoyl group, which usually has 2 carbon atoms,
  • an alkyl group, an alkoxy group, a diarylamino group, an aromatic hydrocarbon group, or an aromatic heterocyclic group is preferable.
  • the substituent is preferably an aromatic hydrocarbon group or an aromatic heterocyclic group, more preferably an aromatic hydrocarbon group, and further preferably having no substituent.
  • an alkyl group or an alkoxy group is preferable as the substituent.
  • each substituent of the above-mentioned substituent group Z may further have a substituent.
  • substituents include the same substituents as the above-mentioned substituents (substituent group Z).
  • Each substituent that the substituent group Z may have is preferably an alkyl group having 8 or less carbon atoms, an alkoxy group having 8 or less carbon atoms, or a phenyl group, and more preferably an alkyl group having 6 or less carbon atoms. It is an alkoxy group or a phenyl group having 6 or less carbon atoms, and it is more preferable that each of the substituents of the substituent group Z does not have a further substituent from the viewpoint of charge transportability.
  • the compound II represented by the formula (200) is a small molecule material, and the molecular weight is preferably 3,000 or less, more preferably 3,000 or less, particularly preferably 2,000 or less, and most preferably. It is 1,500 or less.
  • the lower limit of the molecular weight of compound II is usually 300 or more, preferably 350 or more, and more preferably 400 or more.
  • the compound II represented by the formula (200) is not particularly limited, and examples thereof include the following compounds.
  • composition for forming a light emitting layer of the present invention may contain only one kind of compound II represented by the above formula (200), or may contain two or more kinds.
  • composition for forming a light emitting layer of the present invention in one embodiment is selected from a compound represented by the following formula (210), a compound represented by the following formula (220), and a compound represented by the following formula (230). Contains one or more compounds III.
  • Ar 41 , Ar 42 , and Ar 43 are each independently an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, and an aromatic having 3 to 30 carbon atoms which may have a substituent.
  • R 21 , R 22 and R 23 each independently represent a hydrogen atom or a substituent.
  • X 21 and X 22 independently represent O, S, or N-Ar 44 , respectively.
  • Ar 44 contains an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, an aromatic heterocyclic group having 3 to 30 carbon atoms which may have a substituent, or a substituent. Two to five structures selected from an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have and an aromatic heterocyclic group having 3 to 30 carbon atoms which may have a substituent are linked. Represents a monovalent group n21, n22, and n23 independently represent 1 or 2, respectively. n24 represents an integer from 1 to 4 and represents When n24 is 2 or more, the plurality of R 21s may be the same or different. )
  • the compound III represented by the above formula (210), the above formula (220), or the above formula (230) is preferably a charge transport compound, that is, a charge transport host material.
  • the 6-membered ring is the aromatic hydrocarbon group having 6 to 30 carbon atoms applicable to Ar 41 , Ar 42 , Ar 43 and Ar 44 in the formula (210), the formula (220) and the formula (230).
  • a monovalent group of a monocyclic ring or a monovalent group of 2 to 5 fused rings is preferable.
  • monovalent rings such as benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, fluorene ring, perylene ring, tetracene ring, pyrene ring, benzpyrene ring, chrysene ring, triphenylene ring, fluoranthene ring, and indenofluorene ring.
  • monovalent rings such as benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, fluorene ring, perylene ring, tetracene ring, pyrene ring, benzpyrene ring, chrysene ring, triphenylene ring, fluoranthene ring, and indenofluorene ring.
  • monovalent rings such as benzene ring, naphthalene ring, anthracene ring, phenant
  • it is a monovalent group of a benzene ring, a naphthalene ring, a phenanthrene ring, a fluorene ring, or an indenofluorene ring, and more preferably, it is a monovalent group of a benzene ring, a naphthalene ring, or a fluorene ring. It is preferably a monovalent group of a benzene ring or a naphthalene ring.
  • the aromatic heterocyclic group having 3 to 30 carbon atoms applicable to Ar 41 , Ar 42 , Ar 43 and Ar 44 in the formula (210), the formula (220) and the formula (230) is 5 or 6
  • a monocyclic member ring or a monovalent group of 2 to 5 fused rings is preferable.
  • thiophene ring preferably thiophene ring, pyrrole ring, imidazole ring, pyridine ring, pyrimidine ring, triazine ring, quinoline ring, quinazoline ring, carbazole ring, dibenzofuran ring, dibenzothiophene ring, indolocarbazole ring, phenanthroline ring, or India.
  • locarbazole ring more preferably a monovalent group of a pyridine ring, a pyrimidine ring, a triazine ring, a quinoline ring, a quinazoline ring, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, an indolocarbazole ring, or an indenocarbazole ring.
  • Yes more preferably a monovalent group of a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, an indolocarbazole ring, or an indenocarbazole ring.
  • Ar 41 , Ar 42 , Ar 43 or Ar 44 may have a substituent may have a 6 to 30 carbon aromatic hydrocarbon group and may have a substituent 3 to 30 carbon atoms.
  • the aromatic hydrocarbon group and the aromatic heterocyclic group when the structure selected from the group heterocyclic groups is a monovalent group in which 2 to 5 are linked can be selected and combined from these monovalent groups. ..
  • the number of concatenations is preferably 2 or 3, and more preferably 2.
  • Ar 44 preferably has an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent or an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent. It is a 5 linked group.
  • X 21 is preferably O or N-Ar 44
  • X 22 is preferably O or S, and more preferably O.
  • the substituents that these groups may have can be selected from the substituent group Z in the above-mentioned compound II.
  • Preferred groups of Ar 41 , Ar 42 and Ar 43 include groups represented by the following formulas (20-1) to (20-13), and these groups may further have a substituent.
  • Ar 45 contains an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, an aromatic heterocyclic group having 3 to 30 carbon atoms which may have a substituent, or a substituent. Two to five structures selected from an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have and an aromatic heterocyclic group having 3 to 30 carbon atoms which may have a substituent are linked. It is a monovalent group. )
  • the same group as the monovalent group applicable to the Ar 44 can be applied.
  • the substituent is preferably selected from the above-mentioned substituent group Z. Preferred substituents are also as described in the above-mentioned substituent group Z.
  • R 21 , R 22 , R 23 can each be independently selected from the above-mentioned substituent group Z. It is preferably an aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent or an aromatic heterocyclic group having 3 to 30 carbon atoms which may have a substituent. From the viewpoint of improving durability and charge transportability, it is more preferable to use an aromatic hydrocarbon group which may have a substituent. When there are a plurality of R 21s as substituents, they may be different from each other.
  • R 21 , R 22 and R 23 may have when they are substituents can be selected from the above-mentioned substituent group Z.
  • the compound III represented by the formula (210), the formula (220) or the formula (230) is a small molecule material, and the molecular weight is preferably 3,000 or less, more preferably 3,000 or less, and particularly. It is preferably 2,000 or less, and most preferably 1,500 or less.
  • the lower limit of the molecular weight of compound III is usually 300 or more, preferably 350 or more, and more preferably 400 or more.
  • the compound III represented by the formula (210), the formula (220) or the formula (230) is not particularly limited, and examples thereof include the following compounds.
  • the composition for forming a light emitting layer of the present invention may contain only one kind of the compound represented by the above formula (210) as compound III, or may contain two or more kinds.
  • the composition for forming a light emitting layer of the present invention may contain only one kind of the compound represented by the above formula (220) as compound III, or may contain two or more kinds.
  • the composition for forming a light emitting layer of the present invention may contain only one kind of the compound represented by the above formula (230) as compound III, or may contain two or more kinds.
  • one or more compounds represented by the above formula (210) and one or two compounds represented by the above formula (220) are included.
  • Species or more may be contained, and one or more of the compounds represented by the formula (210) and one or more of the compounds represented by the formula (230) are contained. Also, one or more of the compounds represented by the formula (220) and one or more of the compounds represented by the formula (230) may be contained, and the above formula (210) may be contained. ), One or more of the compounds represented by the above formula (220), and one or more of the compounds represented by the above formula (230). And may be included.
  • composition for forming a light emitting layer of the present invention contains compound IV represented by the following formula (240).
  • Ar 611 and Ar 612 each independently represent a divalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent.
  • R 611 and R 612 are monovalent aromatic hydrocarbon groups having 6 to 50 carbon atoms, which may independently have a deuterium atom, a halogen atom, or a substituent.
  • G represents a divalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a single bond or a substituent.
  • n 611 and n 612 are each independently an integer of 0 to 4.
  • Ar 611 and Ar 612 each independently represent a divalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a substituent.
  • the number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 50, more preferably 6 to 30, and even more preferably 6 to 18.
  • Specific examples of the aromatic hydrocarbon group include a benzene ring, a naphthalene ring, an anthracene ring, a tetraphenylene ring, a phenanthracene ring, a chrysen ring, a pyrene ring, a benzoanthracene ring, or a perylene ring, which usually have 6 carbon atoms.
  • the monovalent group of the aromatic hydrocarbon structure which is usually 30 or less, preferably 18 or less, more preferably 14 or less, or a plurality of structures selected from these structures are bonded in a chain or branched manner.
  • the monovalent group of the structure described above can be mentioned.
  • a structure in which 2 to 8 rings are linked is usually mentioned, and a structure in which 2 to 5 rings are linked is preferable.
  • a plurality of aromatic hydrocarbon rings are linked, the same structure may be linked or different structures may be linked.
  • Ar 611 and Ar 612 are preferably independently phenyl groups, respectively.
  • the number of benzene rings, naphthalene rings, phenanthrene rings and tetraphenylene rings to be bonded is usually 2 to 8, preferably 2 to 5.
  • a monovalent structure in which 1 to 4 benzene rings are linked a monovalent structure in which 1 to 4 benzene rings and a naphthalene ring are linked, a monovalent structure in which 1 to 4 benzene rings and a phenanthrene ring are linked 1 are preferable. It is a valent structure or a monovalent structure in which 1 to 4 benzene rings and a tetraphenylene ring are linked.
  • aromatic hydrocarbon groups may have a substituent.
  • the substituents that the aromatic hydrocarbon group may have are as described above, and specifically, it can be selected from the substituent group Z.
  • the preferred substituent is the preferred substituent of the substituent group Z.
  • At least one of Ar 611 and Ar 612 preferably has at least one partial structure selected from the following formulas (72-1) to (72-7) from the viewpoint of solubility and durability of the compound.
  • * represents a bond with an adjacent structure or a hydrogen atom, and at least one of two * represents a bond position with an adjacent structure.
  • * represents a bond with an adjacent structure or a hydrogen atom
  • * represents a bond position with an adjacent structure.
  • the definition of * is the same unless otherwise specified.
  • At least one of Ar 611 and Ar 612 has at least one partial structure selected from formulas (72-1) to (72-4) and formula (72-7). More preferably, Ar 611 and Ar 612 each have at least one partial structure selected from formulas (72-1) to (72-3) and formula (72-7). Particularly preferably, Ar 611 and Ar 612 each have at least one partial structure selected from formula (72-1), formula (72-2) and formula (72-7).
  • the formula (72-2) is preferably the following formula (72-2-2).
  • a partial structure represented by the formula (72-1) and a partial structure represented by the formula (72-2) are represented as a partial structure preferably possessed by at least one of Ar 611 and Ar 612 .
  • a partial structure having a partial structure to be formed is mentioned.
  • R611 and R612 are monovalent aromatic hydrocarbons having 6 to 30 carbon atoms which may independently have halogen atoms such as deuterium atoms and fluorine atoms, and substituents.
  • the aromatic hydrocarbon group include a monovalent group having an aromatic hydrocarbon structure having preferably 6 to 30 carbon atoms, more preferably 6 to 18 carbon atoms, and more preferably 6 to 10 carbon atoms. These aromatic hydrocarbon groups may have a substituent.
  • the substituents that the aromatic hydrocarbon group may have are as described above, and specifically, it can be selected from the substituent group Z.
  • the preferred substituent is the preferred substituent of the substituent group Z.
  • n 611 and n 612 are each independently an integer of 0 to 4. It is preferably 0 to 2, and more preferably 0 or 1.
  • ⁇ G> G represents a divalent aromatic hydrocarbon group having 6 to 50 carbon atoms which may have a single bond or a substituent.
  • the carbon number of the aromatic hydrocarbon group of G is preferably 6 to 50, more preferably 6 to 30, and even more preferably 6 to 18.
  • Specific examples of the aromatic hydrocarbon group include a benzene ring, a naphthalene ring, an anthracene ring, a tetraphenylene ring, a phenanthracene ring, a chrysen ring, a pyrene ring, a benzoanthracene ring, or a perylene ring, which usually have 6 carbon atoms.
  • a divalent group of an aromatic hydrocarbon structure which is usually 30 or less, preferably 18 or less, more preferably 14 or less, or a plurality of structures selected from these structures are bonded in a chain or branched manner.
  • the divalent group of the structure described above can be mentioned.
  • a structure in which 2 to 8 rings are linked is usually mentioned, and a structure in which 2 to 5 rings are linked is preferable.
  • a plurality of aromatic hydrocarbon rings are linked, the same structure may be linked or different structures may be linked.
  • G is preferably Single bond, Phenylene group, A divalent group in which multiple benzene rings are chained or branched and bonded, A divalent group in which one or more benzene rings and at least one naphthalene ring are chained or branched. A divalent group in which one or more benzene rings and at least one phenanthrene ring are chained or branched and bonded, or A divalent group in which one or more benzene rings and at least one tetraphenylene ring are chained or branched. It is more preferably a divalent group in which a plurality of benzene rings are chained or branched and bonded, and in any case, the order of bonding does not matter.
  • the number of benzene rings, naphthalene rings, phenanthrene rings and tetraphenylene rings to be bonded is usually 2 to 8, preferably 2 to 5. More preferably, a divalent structure in which 1 to 4 benzene rings are linked, a divalent structure in which 1 to 4 benzene rings and a naphthalene ring are linked, a divalent structure in which 1 to 4 benzene rings are linked, and a phenanthrene ring are linked. It is a divalent structure or a divalent structure in which 1 to 4 benzene rings and a tetraphenylene ring are linked.
  • aromatic hydrocarbon groups may have a substituent.
  • the substituents that the aromatic hydrocarbon group may have are as described above, and specifically, it can be selected from the substituent group Z in the above-mentioned compound II.
  • the preferred substituent is the preferred substituent of the substituent group Z in the compound II.
  • Organic solvent contained in the composition for forming a light emitting layer of the present invention is used to form a layer containing the polycyclic heterocyclic compound represented by the formula (1) and compounds I to IV by wet film formation. It is a volatile liquid component.
  • the organic solvent is not particularly limited as long as it is an organic solvent in which the polycyclic heterocyclic compound represented by the formula (1), the compounds I to IV and the second host material described later are well dissolved.
  • Preferred organic solvents include, for example, alkanes such as n-decane, cyclohexane, ethylcyclohexane, decalin, bicyclohexane; aromatic hydrocarbons such as toluene, xylene, mesitylene, phenylcyclohexane, tetraline, methylnaphthalene; chlorobenzene, di.
  • alkanes such as n-decane, cyclohexane, ethylcyclohexane, decalin, bicyclohexane
  • aromatic hydrocarbons such as toluene, xylene, mesitylene, phenylcyclohexane, tetraline, methylnaphthalene
  • chlorobenzene di.
  • Halogenized aromatic hydrocarbons such as chlorobenzene and trichlorobenzene; 1,2-dimethoxybenzene, 1,3-dimethoxybenzene, anisole, phenetol, 2-methoxytoluene, 3-methoxytoluene, 4-methoxytoluene, 2,3 -Aromatic ethers such as dimethylanisole, 2,4-dimethylanisole and diphenyl ether; aromatic esters such as phenylacetate, phenylpropionate, methyl benzoate, ethyl benzoate, propyl benzoate and n-butyl benzoate; Aromatic ketones such as cyclohexanone, cyclooctanone, fencon; alicyclic alcohols such as cyclohexanol and cyclooctanol; aliphatic ketones such as methylethylketone and dibutylketone; aliphatic alcohols such
  • alkanes, aromatic hydrocarbons and aromatic esters are preferable, and aromatic hydrocarbons and aromatic esters are particularly preferable.
  • One of these organic solvents may be used alone, or two or more of them may be used in any combination and ratio.
  • the boiling point of the organic solvent used is usually 80 ° C. or higher, preferably 100 ° C. or higher, more preferably 120 ° C. or higher, and usually 350 ° C. or lower, preferably 330 ° C. or lower, more preferably 300 ° C. or lower. If the boiling point of the organic solvent is lower than this range, the film formation stability may decrease due to solvent evaporation from the light emitting layer forming composition during wet film formation. If the boiling point of the organic solvent exceeds this range, the film formation stability may decrease due to the solvent remaining after the wet film formation.
  • organic solvents it is considered preferable to combine two or more organic solvents having a boiling point of 150 ° C. or higher because it is easy to form a more uniform coating film.
  • composition for forming a light emitting layer of the present invention preferably further contains a second host material.
  • the second host material is preferably a charge-transporting host material, and materials conventionally used as materials for organic electroluminescent devices can be used.
  • materials conventionally used as materials for organic electroluminescent devices can be used.
  • pyridine carbazole, naphthalene, perylene, pyrene, anthracene, chrysene, naphthalene, phenanthrene, coronen, fluoranthene, benzophenanthrene, fluorene, acetonaftofluoranthene, coumarin, p-bis (2-phenylethenyl) benzene and theirs.
  • One of these may be used alone, or two or more of them may be used in any combination and ratio.
  • anthracene derivative a compound represented by the following formula (30) is preferable.
  • the anthracene derivative represented by the following formula (30) has excellent electron transport properties, and when used as a host material for the light emitting layer of an organic electroluminescent device, functions as an electron transport host.
  • Ar 241 and Ar 242 are each independently represented by the following formula (31), Ar 243 represents a substituent, and when there are a plurality of Ar 243s , the plurality of Ar 243s are present. It may be the same or different, and n 43 is an integer of 0 to 8.
  • Ar 244 and Ar 245 each independently represent an aromatic hydrocarbon structure which may have a substituent or a heteroaromatic ring structure which may have a substituent.
  • the plurality of Ar 244 and Ar 245 may be the same or different, and n 44 is an integer of 1 to 5 and n 45 is an integer of 0 to 5.
  • Ar 244 is preferably an aromatic hydrocarbon structure which is a monocyclic or fused ring having 6 to 30 carbon atoms, which may have a substituent, and more preferably may have a substituent.
  • An aromatic hydrocarbon structure which is a monocyclic or fused ring having 6 to 12 carbon atoms.
  • the aromatic hydrocarbon structure is more preferably a benzene ring structure, a naphthalene structure, an anthracene structure, or a phenanthrene structure, and further preferably a benzene ring structure.
  • Ar 245 preferably has an aromatic hydrocarbon structure which is a monocyclic or fused ring having 6 to 30 carbon atoms, which may have a substituent, or may have a substituent, which may have 6 carbon atoms. It is an aromatic heterocyclic structure which is a fused ring of to 30 and more preferably an aromatic hydrocarbon structure which is a monocycle or a fused ring having 6 to 12 carbon atoms which may have a substituent, or It is an aromatic heterocyclic structure which is a fused ring having 12 carbon atoms which may have a substituent.
  • aromatic hydrocarbon structure specifically, a benzene ring structure, a naphthalene structure, an anthracene structure, and a phenanthrene structure are preferable, and a benzene ring structure, a naphthalene structure, or a phenanthrene structure is more preferable.
  • aromatic heterocyclic structure specifically, a dibenzofuran structure, a dibenzothiophene structure, and a phenanthroline structure are preferable, and a dibenzofuran structure or a phenanthroline structure is more preferable.
  • n 44 is preferably an integer of 1 to 3, more preferably 1 or 2.
  • n 45 is preferably an integer of 0 to 3, and more preferably an integer of 0 to 2.
  • the substituents that the substituents Ar 243 , Ar 244 and Ar 245 may have are preferably a group selected from the substituent group Z in the above-mentioned compound II, and more preferably contained in the above-mentioned substituent group Z. It is an alkyl group or an aromatic hydrocarbon group, and more preferably an aromatic hydrocarbon group contained in the above-mentioned substituent group Z. Further, the substituents that may be possessed by the substituents Ar 243 , Ar 244 and Ar 245 may further have a substituent, and the substituents that may further have are the above-mentioned substituents.
  • the same group as the group Z can be mentioned, preferably an alkyl group having 8 or less carbon atoms, an alkoxy group having 8 or less carbon atoms, or a phenyl group, and more preferably an alkyl group having 6 or less carbon atoms and 6 or less carbon atoms. It is more preferably an alkoxy group or a phenyl group, and each of the above-mentioned substituents of the substituent group Z does not have a further substituent from the viewpoint of charge transportability.
  • the compound represented by the formula (30) is a low molecular weight material, and the molecular weight is preferably 3,000 or less, more preferably 2,500 or less, particularly preferably 2,000 or less, and most preferably 1. , 500 or less, usually 300 or more, preferably 350 or more, more preferably 400 or more.
  • the anthracene derivative represented by the formula (30) is not particularly limited, and examples thereof include the following compounds.
  • the content of the polycyclic heterocyclic compound represented by the formula (1) contained in the composition for forming a light emitting layer of the present invention is usually 0.001% by mass or more, preferably 0.01% by mass or more, and is usually 30. It is 0.0% by mass or less, preferably 20.0% by mass or less.
  • the content of the compounds I to IV contained in the composition for forming a light emitting layer of the present invention is usually 0.01% by mass or more, preferably 0.1% by mass or more, and usually 30.0% by mass or less, preferably 30.0% by mass or less. It is 20.0% by mass or less.
  • the polycyclic heterocyclic compound represented by the formula (1) may be contained in the composition for forming a light emitting layer only at one type, or may be contained in combination of two or more types.
  • the compounds I to IV only one kind may be contained in the composition for forming a light emitting layer, or two or more kinds may be contained in combination.
  • the content thereof is usually 0.01% by mass or more, preferably 0.1% by mass or more, and usually 30.0% by mass or less. It is preferably 20.0% by mass or less.
  • the total content of the compounds I to IV and the second host material contained in the light emitting layer forming composition of the present invention is represented by the formula (1) in the light emitting layer forming composition.
  • 1 part by mass of the represented polycyclic heterocyclic compound it is usually 1000 parts by mass or less, preferably 100 parts by mass or less, more preferably 50 parts by mass or less, and usually 0.01 parts by mass or more, preferably 0. It is 1 part by mass or more, more preferably 1 part by mass or more.
  • the light emitting layer of the present invention is considered to appropriately suppress the movement of electric charges in the light emitting layer, further improve the balance between electrons and holes, improve the light emitting efficiency, and extend the driving life of the element.
  • the content of the compounds I to IV is usually 100 parts by mass or less, preferably 70 parts by mass or less, and further, with respect to the total content of 100 parts by mass of the compounds I to IV and the second host material contained in the composition for formation. It is preferably 50 parts by mass or less, usually 1 part by mass or more, preferably 3 parts by mass or more, and more preferably 10 parts by mass or more.
  • the content of the organic solvent contained in the composition for forming a light emitting layer of the present invention is usually 10% by mass or more, preferably 50% by mass or more, particularly preferably 80% by mass or more, and usually 99.95% by mass or less, preferably 99.95% by mass or less. Is 99.9% by mass or less, particularly preferably 99.8% by mass or less.
  • the content of the organic solvent is at least the above lower limit, the viscosity is appropriate and the coatability is improved, and when it is at least the above upper limit, a uniform film can be easily obtained and the film forming property is good.
  • composition for forming a light emitting layer of the present invention may contain other compounds in addition to the above compounds, if necessary.
  • Preferred examples of the other compound include phenols such as dibutylhydroxytoluene and dibutylphenol, which are known as antioxidants.
  • the method for forming a light emitting layer using the composition for forming a light emitting layer of the present invention is a wet film forming method.
  • the wet film forming method is a method in which a composition is applied to form a liquid film, and the film is dried to remove an organic solvent to form a film of a light emitting layer.
  • Examples of the coating method include spin coating method, dip coating method, die coating method, bar coating method, blade coating method, roll coating method, spray coating method, capillary coating method, inkjet method, nozzle printing method, screen printing method, and gravure.
  • a spin coating method, a spray coating method, an inkjet method, a nozzle printing method and the like are preferable.
  • an inkjet method or a nozzle printing method is preferable, and an inkjet method is particularly preferable.
  • the drying method is not particularly limited, but natural drying, vacuum drying, heat drying, or vacuum drying while heating can be appropriately used.
  • the heat drying may be carried out after natural drying or vacuum drying to further remove the residual organic solvent.
  • vacuum drying it is preferable to reduce the pressure to the vapor pressure or lower of the organic solvent contained in the composition for forming a light emitting layer.
  • the heating method is not particularly limited, but heating by a hot plate, heating in an oven, infrared heating, or the like can be used.
  • the heating time is usually 80 ° C. or higher, preferably 100 ° C. or higher, more preferably 110 ° C. or higher, more preferably 200 ° C. or lower, and even more preferably 150 ° C. or lower.
  • the heating time is usually 1 minute or more, preferably 2 minutes or more, usually 60 minutes or less, preferably 30 minutes or less, and more preferably 20 minutes or less.
  • the organic electroluminescent element according to one aspect of the present invention includes an anode, a cathode, and a light emitting layer formed between the anode and the cathode using the composition for forming a light emitting layer of the present invention.
  • the composition for forming a light emitting layer according to one aspect of the present invention contains the polycyclic heterocyclic compound represented by the formula (1) as a light emitting material, and the compound I, the compound II, and the compound III as host materials. , Or at least one of the above-mentioned compound IV, and further contains an organic solvent.
  • the composition for forming a light emitting layer according to one aspect of the present invention preferably contains the second host material, and the second host material is preferably a compound represented by the formula (30).
  • the light-emitting material contained in the composition for forming a light-emitting layer according to one aspect of the present invention is preferably only the polycyclic heterocyclic compound represented by the formula (1), and the host material is the compound I, the above-mentioned compound I. It is more preferable that only the compound II, the compound III, or at least one of the compound IV, and the compound represented by the formula (30) are used.
  • the organic electroluminescent element according to another aspect of the present invention has an anode, a cathode, and a light emitting layer provided between the anode and the cathode, and the light emitting layer is represented by the above formula (1).
  • the electroluminescent layer preferably contains at least one of a ring heterocyclic compound and compounds I to IV, and the light emitting layer further preferably contains the second host material, and the second host material is the formula (30).
  • the compound represented by is preferable.
  • the light-emitting material contained in the light-emitting layer of the organic electroluminescent device according to another aspect of the present invention is preferably only the polycyclic heterocyclic compound represented by the formula (1), and the host material is the compound I. , The compound II, the compound III, and at least one of the compound IV, and the compound represented by the formula (30) are more preferable.
  • the host material as an electron transporting host material, from the viewpoint that it is easy to improve the charge balance of electrons and holes in the light emitting layer by including a material having electron transporting property and a material having hole transporting property.
  • the second host material may contain at least one of the compound represented by the formula (30) and the compound II, and the hole transporting host material may contain at least one of the compound III and the compound IV. preferable.
  • the organic electroluminescent device of the present invention further includes an organic layer other than the light emitting layer as a second organic layer between the anode and the light emitting layer.
  • the second organic layer is more preferably a hole injection layer or a hole transport layer, and even more preferably a hole transport layer.
  • the second organic layer is a polymer having a triarylamine structure as a repeating unit (hereinafter, the polymer contained in the second organic layer is referred to as a "second polymer". There is.), And it is more preferable that the polymer does not contain a cross-linking group.
  • a polymer containing a repeating unit represented by the formula (50) is preferable as described below, and more preferably, a repeating unit represented by the formula (54) described later, the formula (55).
  • a polymer containing a repeating unit represented by the formula (56), a repeating unit represented by the formula (57), a repeating unit represented by the formula (60), or a repeating unit represented by the formula (60) is preferable.
  • the second organic layer is preferably formed by a wet film forming method using a second composition described later.
  • the second composition is insolubilized by heating after coating. Therefore, the second organic layer can be suitably used for stacking organic electroluminescent devices.
  • the second organic layer included in the organic electroluminescent device of the present invention will be described below.
  • the structure of the organic electroluminescent device of the present invention will be described later.
  • the second organic layer preferably contains, as a hole transporting material, a second polymer having a triarylamine structure as a repeating unit, and the polymer may have a cross-linking group. It is more preferable that the polymer does not contain a cross-linking group. The reasons why it is preferable not to contain a cross-linking group are described below.
  • a polycyclic heterocyclic compound containing boron has an empty p-orbital on boron and easily reacts with various reactive groups.
  • the hole transport layer in contact with the light emitting layer is made of a material that does not have a cross-linking group, the unreacted cross-linking group and the polycyclic heterocyclic compound containing boron do not chemically react when the element is driven, and the stability is improved. It is thought to improve.
  • the polymer contained in the second organic layer preferably has a triarylamine structure as a repeating unit.
  • the triarylamine structure is preferably contained in the backbone of the polymer.
  • a polymer having a triarylamine structure as a repeating unit which is preferable as the polymer contained in the second organic layer, will be described.
  • the substituent is a substituent selected from the substituent group Z in the above-mentioned compound II, or a cross-linking group described later.
  • the repeating unit of the triarylamine structure is represented by the following formula (50).
  • Ar 51 includes an aromatic hydrocarbon group which may have a substituent, an aromatic heterocyclic group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent. Represents a linked group of multiple groups selected from aromatic heterocyclic groups that may have substituents.
  • Ar 52 is a divalent aromatic hydrocarbon group which may have a substituent, a divalent aromatic heterocyclic group which may have a substituent, or the divalent aromatic hydrocarbon group. And at least one group selected from the group consisting of the divalent aromatic heterocyclic group represents a divalent group in which a plurality of groups are directly linked or linked via a linking group.
  • Ar 51 and Ar 52 may form a ring via a single bond or a linking group.
  • Ar 51 is an aromatic hydrocarbon group which may have a substituent, an aromatic heterocyclic group which may have a substituent, or a substituent.
  • the aromatic hydrocarbon group preferably has 6 or more carbon atoms and 60 or less carbon atoms, and specifically, a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, a tetracene ring, a pyrene ring, a benzpyrene ring, and a chrysene ring.
  • Triphenylene ring Triphenylene ring, acenaphthene ring, fluorentene ring, fluorene ring and the like, a monovalent group of a 6-membered ring, a monovalent ring of 2 to 5 fused rings, or a group in which a plurality of these are linked.
  • the "monovalent group of a benzene ring” means a "benzene ring having a monovalent free valence", that is, a phenyl group.
  • the aromatic heterocyclic group preferably has 3 or more carbon atoms and 60 or less carbon atoms, and specifically, a furan ring, a benzofuran ring, a thiophene ring, a benzothiophene ring, a pyrrole ring, a pyrazole ring, an imidazole ring, or an oxadiazole ring.
  • Ar 51 is preferably an aromatic hydrocarbon group which may have a substituent, and above all, a benzene ring or a fluorene ring which may have a substituent from the viewpoints of excellent charge transportability and durability.
  • the monovalent group of the above that is, a phenyl group or a fluorenyl group which may have a substituent is more preferable, a fluorenyl group which may have a substituent is further preferable, and a fluorenyl group which may have a substituent may be possessed.
  • a 2-fluorenyl group is particularly preferred.
  • the substituent that the aromatic hydrocarbon group and the aromatic heterocyclic group of Ar 51 may have is not particularly limited as long as it does not significantly reduce the characteristics of the present polymer.
  • the substituent preferably includes a group selected from the substituent group Z, more preferably an alkyl group, a good lucoxy group, an aromatic hydrocarbon group and an aromatic heterocyclic group, and even more preferably an alkyl group.
  • Ar 51 is preferably a fluorenyl group substituted with an alkyl group having 1 to 24 carbon atoms, and particularly a 2-fluorenyl group substituted with an alkyl group having 4 to 12 carbon atoms. preferable. Further, a 9-alkyl-2-fluorenyl group in which the 9-position of the 2-fluorenyl group is substituted with an alkyl group is preferable, and a 9,9-dialkyl-2-fluorenyl group in which the 9-position is substituted with an alkyl group is particularly preferable.
  • the solubility in a solvent and the durability of the fluorene ring tend to be improved. Furthermore, since both the 9-position and the 9'-position are fluorenyl groups substituted with an alkyl group, the solubility in a solvent and the durability of the fluorene ring tend to be further improved.
  • Ar 51 is preferably a spirobifluorenyl group from the viewpoint of solubility in a coating solvent.
  • Ar 51 As the polymer, at least one of Ar 51 in the repeating unit represented by the above formula (50) contains a monovalent or divalent group in which 2 to 5 benzene rings which may have a substituent are linked.
  • Ar 53 and Ar 54 each independently have a divalent aromatic hydrocarbon group which may have a substituent, an aromatic heterocyclic group which may have a substituent, or a substituent. Represents a divalent group in which a plurality of aromatic heterocyclic groups, which may have an aromatic hydrocarbon group or a substituent which may have a substituent, are directly linked or are linked via a linking group.
  • Ar 55 is an aromatic hydrocarbon group which may have a substituent, an aromatic heterocyclic group which may have a substituent, or an aromatic hydrocarbon group or an aromatic which may have a substituent. Represents a monovalent group in which a plurality of group heterocyclic groups are directly linked or linked via a linking group.
  • Ar 56 represents a hydrogen atom or a substituent.
  • each aromatic hydrocarbon group and each aromatic heterocyclic group may have a substituent
  • Ar 56 in the case of a substituent may have a cross-linking group.
  • the cross-linking group a group selected from the cross-linking group group T described later can be used.
  • Ar 53 and Ar 54 each independently have a divalent aromatic hydrocarbon group and a substituent which may have a substituent.
  • it is a divalent aromatic hydrocarbon group which may have a substituent or a group in which a plurality of divalent aromatic hydrocarbon groups which may have a substituent are linked.
  • the substituent which the aromatic hydrocarbon group and the aromatic heterocyclic group may have may have a bridging group, and the same group as the substituent group Z is preferable.
  • the cross-linking group a group selected from the cross-linking group group T can be used.
  • aromatic hydrocarbon group and aromatic heterocyclic group of Ar 53 and Ar 54 the same aromatic hydrocarbon group and aromatic heterocyclic group as Ar 52 can be used.
  • the same group is used as a divalent group in which a plurality of aromatic hydrocarbon groups which may have a substituent or an aromatic heterocyclic group which may have a substituent are directly linked or linked via a linking group. May be a group in which a plurality of different groups are linked, or a group in which a plurality of different groups are linked may be used.
  • a bivalent group linked to 2 to 10 is mentioned, and a divalent group linked to 2 to 5 is preferable.
  • Ar 53 is preferably a group in which 1 to 6 divalent aromatic hydrocarbon groups which may have a substituent are linked, and a divalent aromatic hydrocarbon group which may have a substituent is preferable.
  • a group in which 2 to 4 groups are linked is more preferable, a group in which 1 to 4 phenylene rings which may have a substituent are linked is more preferable, and a group in which 2 or 4 phenylene rings which may have a substituent are linked are further preferable.
  • Biphenylene is particularly preferred.
  • the plurality of linked divalent aromatic hydrocarbon groups are bonded so as not to be conjugated.
  • Ar 53 may have, the same group as the substituent group Z is preferable. Preferably, Ar 53 has no substituents.
  • Ar 54 is preferably a group in which one or a plurality of divalent aromatic hydrocarbon groups which may be the same or different are linked, from the viewpoint of excellent charge transportability and durability, and the divalent aromatic group is preferable.
  • the group hydrocarbon group may have a substituent. When a plurality of plants are linked, 2 or more and 10 or less are preferable, 6 or less is more preferable, and 3 or less is particularly preferable from the viewpoint of film stability.
  • Preferred aromatic hydrocarbon structures are a benzene ring, a naphthalene ring, an anthracene ring, and a fluorene ring, and more preferably a benzene ring and a fluorene ring.
  • the plurality of linked groups may be a group in which 1 to 4 phenylene rings which may have a substituent are linked, or a group which may have a phenylene ring and a substituent which may have a substituent.
  • a group to which a fluorene ring is linked is preferable. From the viewpoint of spreading LUMO, biphenylene in which two phenylene rings which may have a substituent are linked is particularly preferable.
  • any one of the above-mentioned substituent group Z or a combination thereof can be used. It is preferable that the group is other than the N-carbazolyl group, the indolocarbazolyl group and the indenocarbazolyl group, and more preferable substituents are a phenyl group, a naphthyl group and a fluorenyl group. It is also preferable that it does not have a substituent.
  • Ar 55 includes an aromatic hydrocarbon group which may have a substituent, an aromatic heterocyclic group which may have a substituent, or an aromatic hydrocarbon group which may have a substituent.
  • a group selected from the aromatic heterocyclic groups which may have the substituent is a monovalent group in which a plurality of groups are directly linked or linked via a linking group.
  • it is a monovalent aromatic hydrocarbon group which may have a substituent or a group in which a plurality of monovalent aromatic hydrocarbon groups which may have a substituent are linked.
  • the substituent that the aromatic hydrocarbon group and the aromatic heterocyclic group may have may have a bridging group, and a group similar to the substituent group Z is preferable.
  • a group selected from the cross-linking group group T described later can be used.
  • a plurality When a plurality are linked, it is preferably a divalent group linked by 2 to 10 and a monovalent group linked by 2 to 5.
  • the aromatic hydrocarbon and the aromatic heterocycle the same aromatic hydrocarbon group and aromatic heterocyclic group as Ar 51 can be used.
  • the Ar 55 preferably has a structure represented by any of the following schemes 2. Furthermore, from the viewpoint of distributing the LUMO of the molecule, it is selected from a-1 to a-4, b-1 to b-9, c-1 to c-4, d-1 to d-16, and e1 to e4. Structure is preferable. Furthermore, from the viewpoint of promoting the spread of LUMO of the molecule by having an electron-withdrawing group, a-1 to a-4, b-1 to b-9, d-1 to d-12, and e1 to e4. The structure selected from is preferred.
  • a structure selected from a-1 to a-4, d-1 to d-12, and e1 to e4 is preferable. ..
  • d-1 and d-10 are more preferable, and the benzene ring structure of d-1 is particularly preferable, from the viewpoint of easy synthesis and excellent stability.
  • these structures may have a substituent.
  • "-*" indicates the connection position with Ar 54
  • any one of them indicates the connection position with Ar 54 .
  • R 31 and R 32 of Scheme 2 are linear, branched or cyclic alkyl groups which may independently have a substituent.
  • the number of carbon atoms of the alkyl group is not particularly limited, but in order to maintain the solubility of the polymer, the number of carbon atoms is preferably 1 or more and 6 or less, more preferably 3 or less, and further preferably a methyl group or an ethyl group. ..
  • R 31 and R 32 may be the same or different, but all R 31 and R 32 can be uniformly distributed around the nitrogen atom and are easy to synthesize. Is preferably the same group.
  • any one of the above-mentioned substituent group Z or a combination thereof can be used. From the viewpoint of durability and charge transportability, it is preferable to select from the same substituents that the above Ar 54 may have.
  • Ar 56 represents a hydrogen atom or a substituent.
  • Ar 56 is a substituent, it is not particularly limited, but is preferably an aromatic hydrocarbon group which may have a substituent or an aromatic heterocyclic group which may have a substituent.
  • the preferred structure is the same as the aromatic hydrocarbon structure and the aromatic heterocyclic structure mentioned in Ar 53 to Ar 54 , and is a monovalent structure.
  • Ar 56 When Ar 56 is a substituent, it may have a cross-linking group.
  • a cross-linking group a group selected from the cross-linking group group T described later can be used.
  • Ar 56 is a substituent, it is preferable that it is bonded to the 3-position of carbazole from the viewpoint of improving durability.
  • Ar 56 is preferably a hydrogen atom from the viewpoint of ease of synthesis and charge transportability.
  • Ar 56 is preferably an aromatic hydrocarbon group which may have a substituent or an aromatic heterocyclic group which may have a substituent. , It is more preferable that it is an aromatic hydrocarbon group which may have a substituent.
  • Ar 56 is preferably a hydrogen atom from the viewpoint of ease of synthesis and charge transportability.
  • Ar 56 is an aromatic hydrocarbon group which may have a substituent or an aromatic heterocyclic group which may have a substituent
  • the substituents listed in the substituent group Z are substituted. The same is true for the groups, the preferred substituents are the same, and so are the substituents that these substituents may have.
  • At least one of Ar 51 in the repeating unit represented by the above formula (50) is a group represented by the following formula (52).
  • the reason for this is that in the two carbazole structures in the following formula (52), LUMO is distributed in the aromatic hydrocarbon group or the aromatic heterocyclic group between the nitrogen atoms of each other, and the main chain amine in the formula (50) is distributed. It is considered that the influence on the main chain amine is suppressed and the durability of the main chain amine to electrons and excitons is improved.
  • Ar 61 and Ar 62 are each independently a divalent aromatic hydrocarbon group which may have a substituent or a divalent aromatic heterocyclic group which may have a substituent.
  • Ar 63 to Ar 65 are each independently a hydrogen atom or a substituent. * Represents the bond position to the nitrogen atom in the formula (50). )
  • Ar 63 to Ar 65 each independently represent a hydrogen atom or a substituent.
  • the substituents are not particularly limited, but preferably an aromatic hydrocarbon group which may have a substituent or an aromatic complex which may have a substituent. It is a ring group.
  • the preferred structure of the aromatic hydrocarbon group and the aromatic heterocyclic group is the same as the group mentioned in Ar 51 .
  • Ar 63 to Ar 65 are substituents, it is preferable that Ar 63 to Ar 65 are bonded to the 3-position or 6-position of each carbazole structure from the viewpoint of improving durability.
  • Ar 63 to Ar 65 are preferably hydrogen atoms from the viewpoint of ease of synthesis and charge transportability.
  • Ar 63 to Ar 65 are aromatic hydrocarbon groups which may have a substituent or an aromatic heterocyclic group which may have a substituent from the viewpoint of improving durability and charge transportability. It is preferable, and it is more preferable that it is an aromatic hydrocarbon group which may have a substituent.
  • Ar 63 to Ar 65 are an aromatic hydrocarbon group which may have a substituent or an aromatic heterocyclic group which may have a substituent
  • the substituents include the substituent group Z.
  • Ar 62 is a divalent aromatic hydrocarbon group which may have a substituent or a divalent aromatic heterocyclic group which may have a substituent.
  • the aromatic hydrocarbon group preferably has 6 or more and 60 or less carbon atoms, more preferably 10 or more and 50 or less carbon atoms, and particularly preferably 12 or more and 40 or less carbon atoms.
  • Specific examples of the aromatic hydrocarbon group include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, a tetracene ring, a pyrene ring, a benzpyrene ring, a chrysen ring, a triphenylene ring, an acenaften ring, and a fluoranthene ring.
  • Examples thereof include a 6-membered monocyclic ring, a divalent group of a 2 to 5 fused ring, or a group in which a plurality of these are linked, such as a fluorene ring. When a plurality of these are linked, it is preferably a group to which a plurality of linked divalent aromatic hydrocarbon groups are conjugated.
  • the aromatic heterocyclic group preferably has 3 or more and 60 or less carbon atoms, and specifically, a furan ring, a benzofuran ring, a thiophene ring, a benzothiophene ring, a pyrrole ring, a pyrazole ring, an imidazole ring, an oxadiazole ring, and the like.
  • Indole ring Indole ring, carbazole ring, pyroloymidazole ring, pyrrolopyrazole ring, pyrolopyrole ring, thienopyrol ring, thienothiophene ring, flopyrol ring, furan ring, thienofran ring, benzoisoxazole ring, benzoisothiazole ring, benzoimidazole ring, pyridine ring.
  • Examples of the substituent that these aromatic hydrocarbon groups or aromatic heterocyclic groups may have include the alkyl group, the aralkyl group and the aromatic hydrocarbon group of the substituent group Z. If the steric effect of the substituent causes a twist in the structure of Ar 62 , it is preferable that there is no substituent, and if the steric effect of the substituent does not cause a twist in the structure of Ar 62 , it is preferable to have a substituent. ..
  • the preferred group of Ar 62 is a divalent group of a benzene ring, a naphthalene ring, an anthracene ring, a fluorene ring or a group in which a plurality of these are linked, and more preferably, a divalent group of a benzene ring or a group in which a plurality thereof are linked.
  • the benzene ring is linked with a divalent 1,4-phenylene group
  • the fluorene ring is linked with a divalent 2,7-fluoreneylene group, or these are A plurality of linked groups, most preferably a group containing "1,4-phenylene group-2,7-fluorenylene group-1,4-phenylene group-".
  • the phenylene group has no substituent other than the linking position, because the Ar 62 is not twisted due to the steric effect of the substituent.
  • the fluorene group has a substituent at the 9,9'position from the viewpoint of improving the solubility and the durability of the fluorene structure.
  • Ar 61 is a divalent group linked to the nitrogen atom of the amine in the backbone in formula (52).
  • Ar 61 is a divalent aromatic hydrocarbon group which may have a substituent or a divalent aromatic heterocyclic group which may have a substituent.
  • the aromatic hydrocarbon group of Ar 61 preferably has 6 or more carbon atoms and 60 or less carbon atoms, more preferably 10 or more and 50 or less carbon atoms, and particularly preferably 12 or more and 40 or less carbon atoms.
  • Specific examples of the aromatic hydrocarbon group include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, a tetracene ring, a pyrene ring, a benzpyrene ring, a chrysen ring, a triphenylene ring, an acenaften ring, and a fluoranthene ring.
  • Examples thereof include a 6-membered monocyclic ring, a divalent group of a 2 to 5 fused ring, or a group in which a plurality of these are linked, such as a fluorene ring.
  • the aromatic heterocyclic group of Ar 61 preferably has 3 or more carbon atoms and 60 or less carbon atoms.
  • Synnoline ring Synnoline ring, quinoxaline ring, phenanthridin ring, benzoimidazole ring, perimidine ring, quinazoline ring, quinazolinone ring, azulene ring, etc. Examples thereof include a group in which a plurality of these are linked.
  • aromatic hydrocarbon groups or aromatic heterocyclic groups may have include the alkyl group, the aralkyl group and the aromatic hydrocarbon group of the substituent group Z.
  • divalent aromatic hydrocarbon groups or divalent aromatic heterocyclic groups When a plurality of these divalent aromatic hydrocarbon groups or divalent aromatic heterocyclic groups are linked, it is preferably a group in which a plurality of linked divalent aromatic hydrocarbon groups are bonded so as not to be conjugated. Specifically, it is preferable to include a 1,3-phenylene group or a group having a substituent and having a twisted structure due to the steric effect of the substituent.
  • At least one of Ar 51 in the repeating unit represented by the formula (50) is a group represented by the following formula (53).
  • Ar 71 represents a divalent aromatic hydrocarbon group which may have a substituent.
  • Ar 72 and Ar 73 each independently have an aromatic hydrocarbon group which may have a substituent, an aromatic heterocyclic group which may have a substituent, or a substituent. It represents a monovalent group in which two or more groups selected from a good aromatic hydrocarbon group and an aromatic heterocyclic group which may have a substituent are directly or via a linking group.
  • Ring HA is an aromatic heterocycle containing a nitrogen atom.
  • X 2 and Y 2 independently represent a carbon atom or a nitrogen atom, and when at least one of X 2 and Y 2 is a carbon atom, the carbon atom may have a substituent.
  • Ar 71 is the same group as Ar 53 .
  • the Ar 71 is a group in which one divalent aromatic hydrocarbon group which may have a substituent or 2 to 10 divalent aromatic hydrocarbon groups which may have a substituent are linked.
  • one divalent aromatic hydrocarbon group which may have a substituent or a group in which 2 to 8 divalent aromatic hydrocarbon groups which may have a substituent are linked is further used.
  • a group in which two or more divalent aromatic hydrocarbon groups which may have a substituent are linked is preferable.
  • a group in which 2 to 6 benzene rings which may have a substituent are linked is particularly preferable, and a quaterphenylene group in which 4 benzene rings which may have a substituent are linked are particularly preferable. Most preferred.
  • Ar 71 preferably contains at least one benzene ring linked at positions 1 and 3 which are non-conjugated sites, and more preferably contains 2 or more.
  • Ar 71 is a group in which a plurality of divalent aromatic hydrocarbon groups which may have a substituent are linked, it is preferable that all of them are directly bonded and linked from the viewpoint of charge transportability or durability. ..
  • any one of the above-mentioned substituent group Z or a combination thereof can be used.
  • the preferred range of substituents that Ar 71 may have is similar to the substituents that Ar 71 may have when G is an aromatic hydrocarbon group.
  • X 2 and Y 2 independently represent a C (carbon) atom or an N (nitrogen) atom, respectively. When at least one of X 2 and Y 2 is a C atom, it may have a substituent.
  • both X 2 and Y 2 are N atoms.
  • any one of the above-mentioned substituent group Z or a combination thereof can be used. From the viewpoint of charge transportability, it is more preferable that X 2 and Y 2 do not have a substituent.
  • Ar 72 and Ar 73 each independently have an aromatic hydrocarbon group which may have a substituent, an aromatic heterocyclic group which may have a substituent, or a substituent. It is a monovalent group in which a plurality of two or more groups selected from a good aromatic hydrocarbon group and an aromatic heterocyclic group which may have a substituent are directly or via a linking group are linked.
  • Ar 72 and Ar 73 independently have a-1 to a-4, b-1 to b-9, c-1 to c-4, and d shown in the above scheme 2. It is preferable to have a structure selected from -1 to d-16 and e-1 to e-4.
  • a-1 to a-4, b-1 to b-9, c-1 to c-5, d-1 to A structure selected from d-12 and e-1 to e-4 is preferable.
  • a-1 to a-4, d-1 to d-12, and e-1 to e-4 from the viewpoint of the effect of confining excitons formed in the light emitting layer having a high triplet level.
  • the structure is preferred.
  • a structure selected from d-1 to d-12 and e-1 to e-4 is more preferable.
  • -* Represents a binding site with ring HA. When there are a plurality of "-*", one of them represents a site that binds to the ring HA.
  • any one of the above-mentioned substituent group Z or a combination thereof can be used. From the viewpoint of durability and charge transportability, it is a substituent, and a group similar to the substituent group Z is preferable.
  • Ar 52 examples of the aromatic hydrocarbon group and the aromatic hydrocarbon group in Ar 52 include a group similar to Ar 51 in the formula (50) and having a divalent value. Further, the substituents that the aromatic hydrocarbon group and the aromatic hydrocarbon group may have in Ar 52 are preferably the same groups as those in the substituent group Z.
  • a cross-linking group is a group that reacts with other cross-linking groups located in the vicinity of the cross-linking group to form a new chemical bond by irradiation with heat and / or active energy rays.
  • the reacting group may be the same group as the cross-linking group or a different group.
  • cross-linking group examples include a group containing an alkenyl group, a group containing a conjugated diene structure, a group containing an alkynyl group, a group containing an oxylan structure, a group containing an oxetane structure, a group containing an aziridine structure, an azido group, and a maleic anhydride structure.
  • examples thereof include a group containing an alkenyl group bonded to an aromatic ring, a cyclobutene ring fused to an aromatic ring, and the like.
  • Specific examples of the cross-linking group include a group selected from the following cross-linking group group T.
  • R XL represents a methylene group, an oxygen atom or a sulfur atom
  • R 100 represents an alkyl group which may have a hydrogen atom or a substituent
  • n XL represents 0 to 5. Represents an integer. When there are a plurality of R XLs , they may be the same or different, and when there are a plurality of n XLs , they may be the same or different. * 1 represents the bonding position.
  • These cross-linking groups may have substituents.
  • the substituent that R 100 may have in the case of these cross-linking groups and alkyl groups is preferably the substituent described in the substituent group Z.
  • the polymer having a triarylamine structure as a repeating unit contains a plurality of repeating units represented by these formulas and a plurality of repeating units having different structures in each formula.
  • Ar 51 is the same as Ar 51 in the above formula (50).
  • X is -C (R 207 ) (R 208 )-, -N (R 209 )-or-C (R 211 ) (R 212 ) -C (R 213 ) (R 214 )-.
  • R 201 , R 202 , R 221 and R 222 are alkyl groups which may independently have a substituent, respectively.
  • R 207 to R 209 and R 211 to R 214 each independently have a hydrogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent, or a substituent. It is an aromatic hydrocarbon group that may be used.
  • a and b are independently integers of 0 to 4, respectively.
  • c is an integer from 0 to 3 and d is an integer from 0 to 4,
  • the plurality of R 201s may be the same or different.
  • the plurality of R 202s may be the same or different.
  • the plurality of R 221s may be the same or different.
  • the plurality of R 222s may be the same or different.
  • i and j are each independently an integer of 0 to 3.
  • R 201 , R 202 , R 221 and R 222 are alkyl groups which may independently have a substituent.
  • the alkyl group is a linear, branched or cyclic alkyl group.
  • the number of carbon atoms of the alkyl group is not particularly limited, but in order to maintain the solubility of the polymer, 1 or more is preferable, 8 or less is preferable, 6 or less is more preferable, and 3 or less is more preferable.
  • the alkyl group is more preferably a methyl group or an ethyl group.
  • the plurality of R 201s may be the same or different, and when there are a plurality of R 202s, the plurality of R 202s may be the same or different. It is preferable that all R 201 and R 202 have the same group because the charge can be uniformly distributed around the nitrogen atom and the synthesis is easy.
  • the plurality of R 221s may be the same or different, and when there are a plurality of R 222s, the plurality of R 222s may be the same or different. It is preferable that all R 221 and R 222 have the same group because the charge can be uniformly distributed around the nitrogen atom and the synthesis is easy.
  • R 207 to R 209 and R 211 to R 214 each independently have a hydrogen atom, an alkyl group which may have a substituent, an aralkyl group which may have a substituent, or a substituent. It is an aromatic hydrocarbon group that may be used.
  • the alkyl group is not particularly limited, but since it tends to improve the solubility of the polymer, the number of carbon atoms is preferably 1 or more, preferably 24 or less, further preferably 8 or less, and even more preferably 6 or less. Further, the alkyl group may have a linear, branched or cyclic structure.
  • alkyl group examples include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an i-butyl group, a sec-butyl group, a tert-butyl group and an n-hexyl group.
  • alkyl group examples include an n-octyl group, a cyclohexyl group and a dodecyl group.
  • the aralkyl group is not particularly limited, but the solubility of the polymer tends to be improved, so that the number of carbon atoms is preferably 5 or more, preferably 60 or less, and more preferably 40 or less.
  • aralkyl group examples include 1,1-dimethyl-1-phenylmethyl group, 1,1-di (n-butyl) -1-phenylmethyl group and 1,1-di (n-hexyl) -1.
  • the aromatic hydrocarbon group is not particularly limited, but the solubility of the polymer tends to be improved, so that the number of carbon atoms is preferably 6 or more, preferably 60 or less, and more preferably 30 or less.
  • aromatic hydrocarbon group examples include a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, a tetracene ring, a pyrene ring, a benzpyrene ring, a chrysen ring, a triphenylene ring, an acenaphthene ring, a fluoranthene ring, and a fluorene ring.
  • Examples thereof include a monovalent group of a 6-membered ring, a monovalent ring of 2 to 5 fused rings, or a group in which a plurality of these are linked.
  • R 207 and R 208 are preferably a methyl group or an aromatic hydrocarbon group, R 207 and R 208 are more preferably a methyl group, and R 209 is a phenyl group. Is more preferable.
  • Alkyl groups of R 201 , R 202 , R 221 and R 222 , alkyl groups of R 207 to R 209 and R 211 to R 214 , aralkyl groups and aromatic hydrocarbon groups may have substituents.
  • substituents include the alkyl groups of R 207 to R 209 and R 211 to R 214 , the groups listed as preferable groups of the aralkyl group and the aromatic hydrocarbon group.
  • the alkyl groups of R 201 , R 202 , R 221 and R 222 , the alkyl groups of R 207 to R 209 and R 211 to R 214 , the aralkyl group and the aromatic hydrocarbon group are substituents from the viewpoint of lowering the voltage. It is most preferable not to have.
  • a and b are independently integers of 0 to 4. It is preferable that a + b is 1 or more, further, a and b are preferably 2 or less, and it is more preferable that both a and b are 1.
  • a is 1 or more when c is 1 or more, and b is 1 or more when d is 1 or more. Further, when b is 1 or more, it is preferable that d is also 1 or more.
  • the plurality of a may be the same or different, and when d is 2 or more, the plurality of b may be the same or different.
  • the aromatic ring of the main chain is twisted due to steric hindrance, the polymer has excellent solubility in a solvent, and the coating film formed by a wet film forming method and heat-treated is insoluble in the solvent. Tends to be excellent. Therefore, when a + b is 1 or more, when another organic layer (for example, a light emitting layer) is formed on the coating film by a wet film forming method, the composition for forming a light emitting layer used in the present invention containing an organic solvent is included. Elution of the polymer into the substance is suppressed. As a result, it is considered that the influence on the formed light emitting layer is small and the drive life of the organic electroluminescent element is further extended.
  • another organic layer for example, a light emitting layer
  • c is an integer of 0 to 3 and d is an integer of 0 to 4.
  • c and d are preferably 2 or less, respectively, c and d are more preferably equal, and it is particularly preferable that both c and d are 1 or both c and d are 2.
  • both c and d in the repeating unit represented by the above formula (54) are 1, or both c and d are 2, and both a and b are 2 or 1, R.
  • 201 and R 202 are coupled to each other at symmetrical positions.
  • R 201 and R 202 are bonded at positions symmetrical to each other means that the bonding position of R 201 and R 202 is the binding position of R 201 and R 202 with respect to the fluorene ring, carbazole ring or 9,10 dihydrophenanthrene derivative structure in the formula (54). It means that it is symmetric. At this time, 180 degree rotation about the main chain is regarded as the same structure.
  • R 221 and R 222 are present, they are preferably independently present at the 1-position, 3-position, 6-position, or 8-position with respect to the carbon atom of the benzene ring to which X is bonded.
  • the presence of R 221 and / or R 222 at this position causes the fused ring to which R 221 and / or R 222 is bonded and the adjacent benzene ring on the main chain to be twisted due to steric hindrance, resulting in a polymer.
  • the coating film formed by the wet film forming method and heat-treated tends to have excellent solubility in a solvent, and is preferable.
  • i and j are independently integers of 0 to 3.
  • i and j are each independently, preferably an integer of 0 to 2, and more preferably 0 or 1. It is preferable that i and j are the same integer.
  • R 221 and / or R 222 is preferably bonded to the 1-position and / or 3-position of the benzene ring. .. From the viewpoint of ease of synthesis, i and j are preferably 0.
  • the carbon atom to which R221 or R222 can be bonded at the carbon atom next to the carbon atom to which X is bonded is at the 1st position, and is bonded to the adjacent structure as the main chain.
  • the carbon atom is in the second position.
  • Ar 51 is the same as Ar 51 in the above formula (50), and has an aromatic hydrocarbon group and a substituent which may have a substituent.
  • a plurality of groups selected from an aromatic heterocyclic group which may be present, or an aromatic hydrocarbon group which may have a substituent and an aromatic heterocyclic group which may have a substituent are linked. It is a group.
  • It has an aromatic hydrocarbon group that may have a substituent, an aromatic heterocyclic group that may have a substituent, or an aromatic hydrocarbon group and a substituent that may have a substituent.
  • groups in which a plurality of groups selected from the aromatic heterocyclic groups may be linked include the same group as in the case of Ar 51 in the above formula (50), and the substituent and the preferable structure are also described in the above formula. The same as the case of Ar 51 in (50) can be mentioned.
  • Ar 51 in the repeating unit represented by the above formula (54) is a group represented by the formula (51), the formula (52) or the formula (53).
  • LUMO is distributed in the aromatic hydrocarbon group or the aromatic heterocyclic group between the nitrogen atoms of each other, so that the durability against electrons and excitons tends to be improved. It is believed that there is.
  • X in the above formula (54) has high stability during charge transport, it is preferably -C (R 207 ) (R 208 )-or -N (R 209 )-, and -C (R 207 ). ) (R 208 )-is more preferred.
  • the polymer containing the repeating unit represented by the above formula (54) when there are a plurality of Ar 51 , R 201 , R 202 , R 221 , R 222 , and X, they are different even if they are the same. May be good.
  • the polymer contains a plurality of repeating units having the same structure as the repeating unit represented by the formula (54).
  • the HOMO and LUMO of the repeating units are the same, so that the charges do not concentrate on a specific shallow level and become a trap, and the charge transportability It is considered to be excellent.
  • the repeating unit represented by the above formula (54) is particularly preferably a repeating unit represented by any of the following formulas (54-1) to (54-8).
  • R 201 and R 202 are the same, and R 201 and R 202 are coupled to each other at symmetrical positions.
  • the main chain structure excluding the nitrogen atom in the above formula (54) is not particularly limited, and examples thereof include the following structures.
  • the content of the repeating unit represented by the formula (54) is not particularly limited, but the repeating unit represented by the formula (54) is usually 10 mol% in the polymer. It is preferably contained in an amount of 30 mol% or more, more preferably 40 mol% or more, and further preferably 50 mol% or more.
  • the polymer contained in the second organic layer may be composed of only the repeating unit represented by the formula (54) as the repeating unit, but the purpose is to balance various performances when the organic electroluminescent device is used. Therefore, it may have a repeating unit different from that of the equation (54). In that case, the content of the repeating unit represented by the formula (54) in the polymer is usually 99 mol% or less, preferably 95 mol% or less.
  • the terminal group refers to the structure of the terminal portion of the polymer formed by the end cap agent used at the end of the polymerization of the polymer.
  • the terminal group of the polymer containing the repeating unit represented by the formula (54) is preferably a hydrocarbon group.
  • the hydrocarbon group preferably has 1 or more and 60 or less carbon atoms, more preferably 1 or more and 40 or less, and further preferably 1 or more and 30 or less.
  • hydrocarbon group for example, Carbon such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec-butyl group, tert-butyl group, n-hexyl group, cyclohexyl group, dodecyl group, etc.
  • hydrocarbon groups may further have a substituent, and the substituent that may further have is preferably an alkyl group or an aromatic hydrocarbon group. When there are a plurality of these substituents which may be further present, they may be bonded to each other to form a ring.
  • the terminal group is preferably an alkyl group or an aromatic hydrocarbon group, and more preferably an aromatic hydrocarbon group from the viewpoint of charge transportability and durability.
  • Ar 51 is the same as Ar 51 in the above formula (50) or the above formula (54).
  • R 303 and R 306 are alkyl groups which may independently have a substituent, respectively.
  • R 304 and R 305 are each independently an alkyl group which may have a substituent, an alkoxy group which may have a substituent, or an aralkyl group which may have a substituent.
  • l is 0 or 1 and is m is 1 or 2 and n is 0 or 1 and p is 0 or 1. q is 0 or 1.
  • R 303 , R 306 R 303 and R 306 in the repeating unit represented by the above formula (55) are alkyl groups which may independently have a substituent.
  • Examples of the alkyl group include those similar to those of R 201 and R 202 in the above formula (54), and examples thereof include substituents and preferred structures similar to those of R 201 and R 202 .
  • the plurality of R 303s may be the same or different, and when there are a plurality of R 306s, the plurality of R 306s may be the same or different.
  • R 304 , R 305 ) R 304 and R 305 in the repeating unit represented by the above formula (55) are independently an alkyl group which may have a substituent, an alkoxy group which may have a substituent or a substituent. It is an aralkyl group which may have a group. It is preferably an alkyl group which may have a substituent. It is preferable that R 304 and R 304 are the same.
  • the alkyl group is a linear, branched or cyclic alkyl group.
  • the number of carbon atoms of the alkyl group is not particularly limited, but 1 or more is preferable, 24 or less is preferable, 8 or less is more preferable, and 6 or less is more preferable, because the solubility of the polymer tends to be improved.
  • the alkoxy group is not particularly limited, and the R10 group of the alkoxy group ( ⁇ OR 10 ) may have a linear, branched or cyclic structure, and tends to improve the solubility of the polymer.
  • the number of carbon atoms is preferably 1 or more, preferably 24 or less, and more preferably 12 or less.
  • Specific examples thereof include a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, a hexyloxy group, a 1-methylpentyloxy group, a cyclohexyloxy group and the like.
  • the aralkyl group is not particularly limited, but since it tends to improve the solubility of the polymer, the number of carbon atoms is preferably 5 or more, preferably 60 or less, and more preferably 40 or less.
  • 1,1-dimethyl-1-phenylmethyl group 1,1-di (n-butyl) -1-phenylmethyl group, 1,1-di (n-hexyl) -1-phenylmethyl group , 1,1-di (n-octyl) -1-phenylmethyl group, phenylmethyl group, phenylethyl group, 3-phenyl-1-propyl group, 4-phenyl-1-n-butyl group, 1-methyl- 1-phenylethyl group, 5-phenyl-1-n-propyl group, 6-phenyl-1-n-hexyl group, 6-naphthyl-1-n-hexyl group, 7-phenyl-1-n-heptyl group, Examples thereof include 8-phenyl-1-n-octyl group and 4-phenylcyclohexyl group.
  • L and n are independent of each other, and l + n is preferably 1 or more, more preferably 1 or 2, and even more preferably 2.
  • l + n is in the above range, the solubility of the polymer contained in the second organic layer is increased, and precipitation from the composition for an organic electroluminescent device containing the polymer tends to be suppressed.
  • M represents 1 or 2, and is preferably 1 because the organic electroluminescent device of the present invention can be driven at a low voltage and the hole injection ability, transport ability, and durability tend to be improved.
  • (P and q) p represents 0 or 1 and q represents 0 or 1.
  • the plurality of ps may be the same or different, and when n is 2 or more, the plurality of qs may be the same or different.
  • p and q do not become 0 at the same time, the solubility of the polymer contained in the composition of the present invention tends to be high, and precipitation from the second composition containing the polymer tends to be suppressed.
  • the aromatic ring of the main chain is twisted due to steric hindrance, the polymer is excellently soluble in the solvent, and the coating film formed by the wet film forming method and heat-treated is transferred to the solvent. It tends to be insoluble. Therefore, when p + q is 1 or more, when another organic layer (for example, a light emitting layer) is formed on this coating film by a wet film forming method, the composition for forming another organic layer containing an organic solvent is obtained. Elution of the polymer of the above is suppressed.
  • Ar 51 is the same as Ar 51 in the above formula (50) or the above formula (54), and is an aromatic hydrocarbon group which may have a substituent.
  • It has an aromatic hydrocarbon group that may have a substituent, an aromatic heterocyclic group that may have a substituent, or an aromatic hydrocarbon group and a substituent that may have a substituent.
  • groups in which a plurality of groups selected from the aromatic heterocyclic groups may be linked include the same group as in the case of Ar 51 in the above formula (50), and the substituent and the preferable structure are also described in the above formula. The same as the case of Ar 51 in (50) can be mentioned.
  • the main chain structure excluding the N atom of the repeating unit represented by the formula (55) is not particularly limited, and examples thereof include the following structures.
  • the content of the repeating unit represented by the formula (55) is not particularly limited, but the repeating unit represented by the formula (55) is usually 10 mol% in the polymer. It is preferably contained in an amount of 30 mol% or more, more preferably 40 mol% or more, and particularly preferably 50 mol% or more.
  • the polymer contained in the second organic layer may be composed of only the repeating unit represented by the formula (55) as the repeating unit, but the purpose is to balance various performances when the organic electroluminescent device is used. Therefore, it may have a repeating unit different from that of the equation (55). In that case, the content of the repeating unit represented by the formula (55) in the polymer is usually 99 mol% or less, preferably 95 mol% or less.
  • the terminal group of the polymer containing the repeating unit represented by the formula (55) is the terminal group of the polymer containing the repeating unit represented by the above formula (54).
  • it is preferably a hydrocarbon group. Preferred hydrocarbon groups and possible substituents are also the same as the terminal groups of the polymer containing the repeating unit represented by the above formula (54).
  • Ar 51 is the same as the Ar 51 in the above formula (50), the above formula (54) or the above formula (55).
  • Ar 41 is a divalent aromatic hydrocarbon group which may have a substituent, a divalent aromatic heterocyclic group which may have a substituent, or the divalent aromatic hydrocarbon group. And at least one group selected from the group consisting of the divalent aromatic heterocyclic group is a divalent group in which a plurality of groups are directly linked or linked via a linking group.
  • R 441 and R 442 are alkyl groups which may independently have a substituent, respectively.
  • t is 1 or 2
  • u is 0 or 1 and is r and s are independently integers from 0 to 4.
  • R 441 , R 442 R 441 and R 442 in the repeating unit represented by the above formula (56) are alkyl groups which may independently have a substituent.
  • the alkyl group is a linear, branched or cyclic alkyl group which may have a substituent.
  • the number of carbon atoms of the alkyl group is not particularly limited, but in order to maintain the solubility of the polymer, the number of carbon atoms is preferably 1 or more, preferably 10 or less, more preferably 8 or less, and even more preferably 6 or less.
  • the alkyl group is more preferably a methyl group or a hexyl group.
  • R 441 and R 442 may be the same or different.
  • r and s are independently integers of 0 to 4.
  • t is 2 or more, the plurality of r may be the same or different, and when u is 2 or more, the plurality of s may be the same or different.
  • r + s is preferably 1 or more, and r and s are preferably 2 or less, respectively. When r + s is 1 or more, it is considered that the drive life of the organic electroluminescent device is further extended.
  • t is 1 or 2 and u is 0 or 1.
  • t is preferably 1 and u is preferably 1.
  • Ar 51 is the same as Ar 51 in the above formula (50), the above formula (54) or the above formula (55), and even if it has a substituent.
  • Examples of the aromatic hydrocarbon group which may have a substituent or the aromatic heterocyclic group which may have a substituent include the same as in the case of Ar 51 in the above formula (50). Examples of the substituent and the preferable structure are the same as in the case of Ar 51 in the above formula (50).
  • Ar 41 is a divalent aromatic hydrocarbon group which may have a substituent, a divalent aromatic heterocyclic group which may have a substituent, or the divalent aromatic hydrocarbon group. And at least one group selected from the group consisting of the divalent aromatic heterocyclic group is a divalent group in which a plurality of groups are directly linked or linked via a linking group.
  • Examples of the aromatic hydrocarbon group and the aromatic hydrocarbon group in Ar 41 include the same groups as Ar 52 in the above formula (50). Further, the substituents that the aromatic hydrocarbon group and the aromatic hydrocarbon group may have are preferably the same groups as those of the substituent group Z, and the substituents that may have further are also the substituent group Z. It is preferable that it is the same as.
  • the content of the repeating unit represented by the formula (56) is not particularly limited, but the repeating unit represented by the formula (56) is usually 10 mol% in the polymer. It is preferably contained in an amount of 30 mol% or more, more preferably 40 mol% or more, and particularly preferably 50 mol% or more.
  • the polymer contained in the second organic layer may be composed of only the repeating unit represented by the formula (56) as the repeating unit, but the purpose is to balance various performances when the organic electroluminescent device is used. Therefore, it may have a repeating unit different from that of the equation (56). In that case, the content of the repeating unit represented by the formula (56) in the polymer is usually 99 mol% or less, preferably 95 mol% or less.
  • the terminal group of the polymer containing the repeating unit represented by the formula (56) is the terminal group of the polymer containing the repeating unit represented by the above formula (54).
  • it is preferably a hydrocarbon group. Preferred hydrocarbon groups and possible substituents are also the same as the terminal groups of the polymer containing the repeating unit represented by the above formula (54).
  • the Ar 51 is the same as the Ar 51 in the formula (50), the formula (54), the formula (55) or the formula (56).
  • Each of R 517 to R 519 independently contains an alkyl group which may have a substituent, an alkoxy group which may have a substituent, an aralkyl group which may have a substituent, and a substituent.
  • f, g, and h each independently represent an integer of 0 to 4.
  • e represents an integer from 0 to 3 and represents However, when g is 1 or more, e is 1 or more.
  • R 517 to R 519 The aromatic hydrocarbon group and the aromatic heterocyclic group in R 517 to R 519 are independently the same groups as those mentioned in Ar 51 , and the substitutions that these groups may have.
  • the group is preferably a group similar to the substituent group Z or.
  • the alkyl group and the aralkyl group in R 517 to R 519 are preferably the same group as those mentioned in R 207 , and the substituent which may be possessed is also preferably the same group as in R 207 .
  • the alkoxy group in R 517 to R 519 is preferably the alkoxy group mentioned in the substituent group Z, and the substituents that may be further contained are the same as those in the substituent group Z.
  • (F, g, h) f, g, and h each independently represent an integer of 0 to 4.
  • a plurality of g may be the same or different.
  • f + g + h is 1 or more.
  • f + h is 1 or more.
  • f + h is 1 or more and f, g and h are 2 or less.
  • f + h is 1 or more and f and h are 1 or less. It is most preferable that both f and h are 1.
  • R 517 and R 519 are bonded to each other at symmetrical positions. Further, it is preferable that R 517 and R 519 are the same.
  • g is 2
  • the two R 518s are most preferably bonded to each other in the para position.
  • g it is most preferable that the two R 518s are the same.
  • R 517 and R 519 are coupled to each other at symmetrical positions means the following coupling positions.
  • 180 degree rotation around the main chain is regarded as the same structure.
  • the ratio of the compound represented by the formula (1) to the repeating unit represented by the formula (57) is (formula).
  • the number of moles of the repeating unit represented by (57)) / (the number of moles of the compound represented by the formula (1)) is preferably 0.1 or more, more preferably 0.3 or more, and 0.5 or more. More preferably, 0.9 or more is even more preferable, and 1.0 or more is particularly preferable.
  • the ratio is preferably 2.0 or less, more preferably 1.5 or less, and even more preferably 1.2 or less.
  • repeating unit represented by the above formula (57) is preferably a repeating unit represented by the following formula (58).
  • the bonding positions are the 2nd and 5th positions.
  • g 0, that is, when there is no steric hindrance due to R 518
  • R 517 and R 519 are coupled to each other at a symmetrical position.
  • the bonding positions are the 2nd and 5th positions.
  • R 517 and R 519 can be coupled to each other at symmetrical positions.
  • the main chain structure of the repeating unit represented by the formula (57) is not particularly limited, and examples thereof include the following structures.
  • the repeating unit represented by any of the formulas (50) to (59) does not have a cross-linking group.
  • the polymer chain is not easily distorted by heating and drying or baking (heating and firing) after the wet film formation. This is because the volume change may occur when the cross-linking group reacts, and the polymer chain is distorted. This is also because the polymer chain is distorted even if the volume does not change.
  • Ar 51 is the same as Ar 51 in the above equation (50).
  • n 60 represents an integer of 1 to 5.
  • n 60 represents an integer of 1 to 5, preferably an integer of 1 to 4, and more preferably an integer of 1 to 3.
  • the repeating unit represented by the formula (50) is more preferably represented by the formula (54).
  • the repeating unit represented by the above formula (54) including the partial structure represented by the following formula (61).
  • the repeating unit represented by the above formula (55) including the partial structure represented by the following formula (61).
  • the repeating unit represented by the above formula (56) including the partial structure represented by the following formula (61).
  • it is preferably a polymer containing a repeating unit represented by the above formula (57) including a partial structure represented by the following formula (61).
  • R 601 is R 201 or R 202 in equation (54), R 303 , R 304 , R 305 or R 406 in equation (55), R 441 or R + in equation (56), R 517 in equation (57), It represents R 518 or R 519 , and-* represents a bond with an adjacent atom.
  • Ring B may be a part of the fused ring.
  • the partial structures represented by the formulas (61) and (61') include Ring A and Ring B, and in the case of the partial structure of the formula (54), R201 or R202 , the formula ( If it is a partial structure of 55), it is R 303 , R 304 , R 305 , or R 406 , if it is a partial structure of equation (56), it is R 441 or R 442 , and if it is a partial structure of equation (57), it is. It may have R 517 , R 518 or R 519 . ) Since the formula (61) and the formula (61') can be regarded as the same, the formula (61) will be described below when necessary.
  • the partial structure represented by the above equation (61) is more main than the normal ⁇ -conjugated bond by distorting the substantially planar structure of Ring A and Ring B formed by ⁇ -conjugation by the steric hindrance of R601 .
  • the chain has a twisted structure. That is, it has a twisted structure that inhibits conjugation. Therefore, the singlet excitation energy level and the triplet excitation energy level are high, excitons in adjacent light emitting layers can be blocked, and the light emission efficiency as a light emitting element tends to be high, which is preferable.
  • the repeating unit of the above formula (54) is particularly preferable. It is more preferable that the composition of the present invention contains the solvent compound represented by the above formula (1) and a polymer having this repeating unit.
  • the repeating unit represented by the formula (54) is preferably a repeating unit represented by the following formula (62).
  • Ar 51 , X, R 201 , R 202 , R 221 , R 222 , a, b, c, d are Ar 51 , X, R 201 , R 202 , R 221 , R 222 , a in the above equation (54).
  • B, c, d, a 1 , a 2 , b 1 , b 2 , i 1 , i 2 , j 1 , and j 2 are independently 0 or 1, respectively.
  • a 1 , a 2 and a are independent of each other, and at least one is 1 or more.
  • b 1 , b 2 and b are independent of each other and at least one is 1 or more.
  • c and d are 1 or more independently, respectively.
  • c is 1
  • at least one of a1 or a2 is 1.
  • d is 1
  • at least one of b1 or b2 is 1.
  • (2) i 1 , i 2 , j 1 and j 2 are independent of each other, and at least one is 1.
  • Ring B1 refers to a divalent benzene ring that may have R 201 in a particular position.
  • Ring B3 refers to a divalent fused ring with a biphenyl structure further bonded at X.
  • Ring B5 refers to a divalent benzene ring that may have R 202 at a particular position.
  • a in the formula (54) is 1 or more is synonymous with the fact that at least one of a 1 , a 2 and a is 1 or more in the formula (62), and is synonymous with the formula (54).
  • b is 1 or more is synonymous with the fact that at least one of b 1 , b 2 and b is 1 or more in the formula (62).
  • the formula (62) includes the formula (61) as a partial structure.
  • a 1 , a 2 and a is 1 or more, If at least one of a 1 or a 2 is 1,
  • Ring B1 and Ring B2 include the above formula (61) as a partial structure.
  • Ring B1 and Ring B3 include the above formula (61) as a partial structure.
  • Ring B2 and Ring B1 or Ring B2 and Ring B3 include the above formula (61) as a partial structure.
  • the above formula (61) may be included as a partial structure in Ring B2.
  • i 1 , i 2 , j 1 and j 2 is 1.
  • the formula (61) is formed as a partial structure by the ring to which R221 of Ring B3 is bonded and the benzene ring of Ring B2 or Ring B1.
  • the ring in which R222 of Ring B3 is bonded and the benzene ring of Ring B4 or Ring B5 may form the formula (61) as a partial structure. I understand. That is, it can be seen that Ring B3 and Ring B2 or Ring B1 have a twisted structure, or Ring B3 and Ring B4 or Ring B5 are twisted.
  • the formula (62) contains a twisted structure of the aromatic ring of the main chain, it is preferable because it is a twisted structure that inhibits conjugation.
  • the weight average molecular weight (Mw) of the polymer containing the repeating unit represented by the formula (54) is usually 3,000,000 or less, preferably 1,000,000 or less, more preferably 500,000 or less, still more preferably. Is 200,000 or less, particularly preferably 100,000 or less.
  • the weight average molecular weight is usually 2,500 or more, preferably 5,000 or more, more preferably 10,000 or more, still more preferably 15,000 or more, and particularly preferably 17,000 or more.
  • the weight average molecular weight of the polymer When the weight average molecular weight of the polymer is not more than the above upper limit value, solubility in a solvent is obtained, and the film forming property tends to be excellent. Further, when the weight average molecular weight of the polymer is at least the above lower limit value, the decrease in the glass transition temperature, the melting point and the vaporization temperature of the polymer may be suppressed, and the heat resistance may be improved.
  • the number average molecular weight (Mn) of the polymer containing the repeating unit represented by the formula (54) is usually 2.5 million or less, preferably 750,000 or less, more preferably 400,000 or less, and particularly preferably. Is 100,000 or less.
  • the number average molecular weight is usually 2,000 or more, preferably 4,000 or more, more preferably 6,000 or more, and further preferably 8,000 or more.
  • the dispersity (Mw / Mn) in the polymer containing the repeating unit represented by the formula (54) is preferably 3.5 or less, more preferably 2.5 or less, and particularly preferably 2.0 or less. .. Since the smaller the value of the dispersion, the better, the lower limit is ideally 1. When the dispersity of the polymer is not more than the above upper limit, purification is easy, and solubility in a solvent and charge transporting ability are good.
  • the weight average molecular weight (Mw) of the polymer containing the repeating unit represented by the formula (55) or the formula (56) is preferably 10,000 or more, more preferably 15,000 or more, still more preferably. It is over 17,000.
  • the weight average molecular weight is preferably 2,000,000 or less, more preferably 1,000,000 or less, and particularly preferably 100,000 or less.
  • the weight average molecular weight of the polymer is not more than the above upper limit, the increase in the molecular weight of impurities is suppressed, and purification tends to be easy. Further, when the weight average molecular weight of the polymer is at least the above lower limit value, the decrease in the glass transition temperature, the melting point, the vaporization temperature and the like is suppressed, and the heat resistance tends to be improved.
  • the number average molecular weight (Mn) of the polymer containing the repeating unit represented by the formula (55) or the formula (56) is preferably 1,000,000 or less, more preferably 800,000 or less. , More preferably 500,000 or less. Further, it is preferably 4,000 or more, more preferably 8,000 or more, and further preferably 10,000 or more.
  • the dispersity (Mw / Mn) of the polymer containing the repeating unit represented by the formula (55) or the formula (56) is preferably 3.5 or less, more preferably 3.0 or less. It is more preferably 2.4 or less, particularly preferably 2.1 or less, and most preferably 2 or less.
  • the dispersity of the polymer is preferably 1 or more, more preferably 1.1 or more, and further preferably 1.2 or more.
  • the weight average molecular weight and the number average molecular weight of the polymer are determined by SEC (size exclusion chromatography) measurement.
  • SEC size exclusion chromatography
  • the weight average molecular weight and the number average molecular weight are calculated.
  • the content of the repeating unit represented by the formula (50) is not particularly limited, but the repeating unit represented by the formula (50) is usually 10 mol% or more in 100 mol% of all the repeating units of the polymer. It is contained, preferably 30 mol% or more, more preferably 40 mol% or more, and further preferably 50 mol% or more.
  • the repeating unit may be composed of only the repeating unit represented by the formula (50), but the polymer is represented by the formula (50) for the purpose of balancing various performances when the organic electroluminescent device is used. It may have a repeating unit different from the repeating unit to be generated. In that case, the content of the repeating unit represented by the formula (50) in the polymer is usually 99 mol% or less, preferably 95 mol% or less.
  • the polymer containing the arylamine structure of the present invention as a repeating unit may further contain a structure represented by the following formula (50-2) in the main chain.
  • R 81 and R 82 each independently represent a hydrogen atom, an alkyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group. When a plurality of R 81 and R 82 are present, they are the same. It may be different. P80 represents an integer of 1 to 5.
  • the alkyl group is a linear, branched or cyclic alkyl group.
  • the number of carbon atoms of the alkyl group is not particularly limited, but in order to maintain the solubility of the polymer, 1 or more is preferable, 8 or less is preferable, 6 or less is more preferable, and 3 or less is further preferable.
  • the alkyl group is more preferably a methyl group or an ethyl group.
  • R 81 and R 82 are aromatic hydrocarbon groups or aromatic heterocyclic groups, the structure described in the above-mentioned "Definition" item is preferable.
  • R 81 and R 82 may have a substituent and / or a cross-linking group.
  • the substituent is preferably a substituent selected from the substituent group Z.
  • the cross-linking group is preferably a cross-linking group selected from the cross-linking group group Z.
  • p80 is preferably 3 or less, more preferably 2 or less, and most preferably 1.
  • the coupling of the main chain of the polymer is broken, the S1 energy level and the T1 energy level of the polymer are increased, and the composition containing this polymer is contained.
  • the hole transport layer of the organic electric field light emitting element it is considered that the excitators of the light emitting layer are less likely to be deactivated and the light emission efficiency is increased, which is preferable.
  • a specific structure in the repeating unit represented by each equation, a specific structure will be referred to as a “repeating unit structure”.
  • the specific structure is a structure obtained by applying a specific structure or numerical value to all the codes in the general formula. That is, the polymer having an arylamine structure as a repeating unit has a repeating unit structure contained in the formula (54), a repeating unit structure contained in the formula (55), and a repeating unit structure contained in the formula (56).
  • the repeating unit structures included in the formula (57) and the repeating unit structure included in the formula (60) only one repeating unit structure may be included, or two or more repeating unit structures may be included. good.
  • the plurality of repetition units of two or more may be the repetition unit structure included in the same general formula, or may be a repetition unit structure included in different general formulas. There may be.
  • the polymer having an arylamine structure as a repeating unit contains 1 or 2 specific repeating unit structures represented by each of these formulas, and does not contain other repeating unit structures. It is even more preferable that they are coalesced.
  • These polymers may be random copolymers, alternate copolymers, block copolymers, graft copolymers, or the like, and the order of arrangement of the monomers is not limited.
  • polymer containing the repeating unit represented by the formula (55) and the polymer having the structure in which Ar 51 of the repeating unit represented by the formula (55) is represented by the formula (52) are shown below.
  • the polymer used in the present invention is not limited to these.
  • the numbers in the chemical formula represent the molar ratio of the repeating unit. n represents the number of repetitions.
  • These polymers may be random copolymers, alternate copolymers, block copolymers, graft copolymers, or the like, and the order of arrangement of the monomers is not limited.
  • polymer containing the repeating unit represented by the formula (56) are shown below, but the polymer used in the present invention is not limited thereto.
  • the numbers in the chemical formula represent the molar ratio of the repeating unit. n represents the number of repetitions.
  • These polymers may be random copolymers, alternate copolymers, block copolymers, graft copolymers, or the like, and the order of arrangement of the monomers is not limited.
  • the method for producing the second polymer contained in the second organic layer is not particularly limited and is arbitrary.
  • a polymerization method by the Suzuki reaction a polymerization method by the Grignard reaction, a polymerization method by the Yamamoto reaction, a polymerization method by the Ullmanne reaction, a polymerization method by the Buchwald-Hartwig reaction and the like can be mentioned.
  • the aryl dihalogenated represented by the following formula (54a) Z represents a halogen atom such as I, Br, Cl, F
  • a second polymer containing the repeating unit represented by the formula (54) is synthesized.
  • the dial halide represented by the formula (55a) Z represents a halogen atom such as I, Br, Cl, F
  • the formula (55b) By reacting with the primary aminoaryl represented by 55b), a polymer containing the repeating unit represented by the formula (55) is synthesized.
  • the reaction for forming an N-aryl bond is usually carried out in the presence of a base such as potassium carbonate, tert-butoxysodium or triethylamine. It can also be carried out in the presence of a transition metal catalyst such as copper or palladium complex.
  • a base such as potassium carbonate, tert-butoxysodium or triethylamine. It can also be carried out in the presence of a transition metal catalyst such as copper or palladium complex.
  • the second composition contains a second polymer and a solvent (organic solvent).
  • This second composition is usually used by a wet film forming method to form an organic layer of the organic electroluminescent device of the present invention.
  • the organic layer is particularly preferably a hole transport layer adjacent to the light emitting layer formed by the composition for forming a light emitting layer of the present invention.
  • the second composition may contain one kind of the second polymer, or may contain two or more kinds in any combination and any ratio.
  • the content of the second polymer in the second composition is usually 0.01% by mass or more and 70% by mass or less, preferably 0.1% by mass or more and 60% by mass or more, and more preferably 0.5% by mass or more. It is 50% by mass or less.
  • the content of the second polymer is within the above range, defects are less likely to occur in the formed organic layer and uneven film thickness is less likely to occur, which is preferable.
  • the second composition usually contains a solvent.
  • the solvent is preferably one that dissolves the second polymer.
  • a solvent in which the second polymer is dissolved in the second composition at room temperature in an amount of usually 0.05% by mass or more, preferably 0.5% by mass or more, still more preferably 1% by mass or more is preferable. Is.
  • the solvent include aromatic solvents such as toluene, xylene, mesitylene, cyclohexylbenzene and methylnaphthalene; halogen-containing solvents such as 1,2-dichloroethane, chlorobenzene and o-dichlorobenzene; ethylene glycol dimethyl ether and ethylene glycol diethyl.
  • aromatic solvents such as toluene, xylene, mesitylene, cyclohexylbenzene and methylnaphthalene
  • halogen-containing solvents such as 1,2-dichloroethane, chlorobenzene and o-dichlorobenzene
  • ethylene glycol dimethyl ether and ethylene glycol diethyl.
  • Alibo ethers such as ethers, propylene glycol-1-monomethyl ether acetate (PGMEA); 1,2-dimethoxybenzene, 1,3-dimethoxybenzene, anisole, phenetol, 2-methoxytoluene, 3-methoxytoluene, 4- Ether-based solvents such as aromatic ethers such as methoxytoluene, 2,3-dimethylanisole and 2,4-dimethylanisole; aliphatic ester-based solvents such as ethyl acetate, n-butyl acetate, ethyl lactate and n-butyl lactate; Ester-based solvents such as phenyl acetate, phenyl propionate, methyl benzoate, ethyl benzoate, isopropyl benzoate, propyl benzoate, n-butyl benzoate and other aromatic esters; organic solvents such as, and other holes described below.
  • One type of solvent may be used, or two or more types may be used in any combination and in any ratio.
  • the surface tension of the solvent at 20 ° C. is usually less than 40 dyn / cm, preferably 36 dyn / cm or less, and more preferably 33 dyn / cm or less.
  • the vapor pressure of the solvent at 25 ° C. is usually 10 mmHg or less, preferably 5 mmHg or less, and usually 0.1 mmHg or more.
  • Such a solvent include the above-mentioned aromatic solvents such as toluene, xylene, mesitylene and cyclohexylbenzene, ether solvents and ester solvents.
  • the solubility of the solvent in water at 25 ° C. is preferably 1% by mass or less, more preferably 0.1% by mass or less.
  • the content of the solvent in the second composition is usually 10% by mass or more, preferably 30% by mass or more, more preferably 50% by mass or more, and particularly preferably 80% by mass or more.
  • the content of the solvent is at least the above lower limit, the flatness and uniformity of the formed layer can be improved.
  • the second composition preferably further contains an electron-accepting compound in terms of lowering the resistance.
  • the second composition preferably contains an electron accepting compound.
  • the electron-accepting compound a compound having an oxidizing power and an ability to receive one electron from the second polymer contained in the second organic layer is preferable. Specifically, a compound having an electron affinity of 4 eV or more is preferable, and a compound having an electron affinity of 5 eV or more is more preferable.
  • the second composition may contain one kind of the above-mentioned electron-accepting compound alone, or may contain two or more kinds in any combination and ratio.
  • the content of the electron-accepting compound in the second composition is usually 0.0005% by mass or more, preferably 0.001% by mass or more, and is usually used. It is 20% by mass or less, preferably 10% by mass or less.
  • the ratio of the electron-accepting compound to the second polymer in the second composition is usually 0.5% by mass or more, preferably 1% by mass or more, more preferably 3% by mass or more, and usually 80% by mass. Hereinafter, it is preferably 60% by mass or less, more preferably 40% by mass or less.
  • the electron acceptor When the content of the electron-accepting compound in the second composition is at least the above lower limit, the electron acceptor receives electrons from the second polymer and the formed organic layer has a low resistance, which is preferable.
  • the content of the electron-accepting compound in the second composition is not more than the above upper limit, defects are less likely to occur in the formed organic layer and uneven film thickness is less likely to occur, which is preferable.
  • the second composition may further contain a cationic radical compound.
  • a cationic radical compound an ionic compound composed of a cationic radical, which is a chemical species obtained by removing one electron from a hole transporting compound, and a counter anion is preferable.
  • the cation radical is derived from a hole-transporting polymer compound, the cation radical has a structure in which one electron is removed from the repeating unit of the polymer compound.
  • the cation radical is preferably a chemical species obtained by removing one electron from the hole transporting compound described later.
  • a chemical species obtained by removing one electron from a preferable compound as a hole transporting compound is preferable in terms of amorphousness, visible light transmittance, heat resistance, solubility and the like.
  • the cationic radical compound can be produced by mixing the hole transporting compound described later and the electron accepting compound described above. By mixing a hole-transporting compound and an electron-accepting compound, electron transfer occurs from the hole-transporting compound to the electron-accepting compound, and a cation consisting of a cation radical and a counter anion of the hole-transporting compound occurs. The compound is produced.
  • the content of the cation radical compound in the second composition is usually 0.0005% by mass or more, preferably 0.001% by mass or more, and usually 40% by mass. Hereinafter, it is preferably 20% by mass or less.
  • the content of the cationic radical compound is not less than the above lower limit, the formed organic layer has a low resistance, and when it is not more than the above upper limit, the formed organic layer is less likely to have defects and uneven film thickness is less likely to occur. ..
  • the second composition may contain components contained in the hole injection layer forming composition and the hole transport layer forming composition described later in the contents described below. ..
  • FIG. 1 shows a schematic view (cross section) of a structural example of the organic electroluminescent device 8.
  • 1 is a substrate
  • 2 is an anode
  • 3 is a hole injection layer
  • 4 is a hole transport layer
  • 5 is a light emitting layer
  • 6 is an electron transport layer
  • 7 is a cathode.
  • the substrate 1 serves as a support for an organic electric field light emitting element, and usually a quartz or glass plate, a metal plate, a metal foil, a plastic film, a sheet, or the like is used. Of these, a glass plate or a transparent synthetic resin plate such as polyester, polymethacrylate, polycarbonate, or polysulfone is preferable.
  • the substrate is preferably made of a material having a high gas barrier property because the organic electroluminescent element is unlikely to be deteriorated by the outside air. Therefore, particularly when a material having a low gas barrier property such as a substrate made of synthetic resin is used, it is preferable to provide a dense silicon oxide film or the like on at least one side of the substrate to improve the gas barrier property.
  • the anode 2 has a function of injecting holes into the layer on the light emitting layer 5 side.
  • the anode 2 is usually a metal such as aluminum, gold, silver, nickel, palladium, platinum; a metal oxide such as an oxide of indium and / or tin; a halide metal such as copper iodide; carbon black and poly (3). -Methylthiophene), polypyrrole, polyaniline and other conductive polymers.
  • the anode 2 is usually formed by a dry method such as a sputtering method or a vacuum vapor deposition method.
  • a dry method such as a sputtering method or a vacuum vapor deposition method.
  • metal fine particles such as silver, fine particles such as copper iodide, carbon black, conductive metal oxide fine particles, conductive polymer fine powder, etc.
  • disperse them in an appropriate binder resin solution it can also be formed by applying it on a substrate.
  • a conductive polymer a thin film can be formed directly on the substrate by electrolytic polymerization, or an anode can be formed by applying the conductive polymer on the substrate (Appl. Phys. Lett., Volume 60, 2711 p., 1992).
  • the anode 2 usually has a single-layer structure, but may have a laminated structure as appropriate. When the anode 2 has a laminated structure, different conductive materials may be laminated on the first-layer anode.
  • the thickness of the anode 2 may be determined according to the required transparency and material. When particularly high transparency is required, a thickness having a visible light transmittance of 60% or more is preferable, and a thickness having a visible light transmittance of 80% or more is further preferable.
  • the thickness of the anode 2 is usually 5 nm or more, preferably 10 nm or more, and usually 1000 nm or less, preferably 500 nm or less.
  • the thickness of the anode 2 may be arbitrarily set according to the required strength and the like, and in this case, the anode 2 may have the same thickness as the substrate.
  • impurities on the anode 2 are removed and the ionization potential thereof is formed by treating the surface of the anode 2 with ultraviolet rays / ozone, oxygen plasma, argon plasma, or the like. It is preferable to improve the hole injection property.
  • the layer having a function of transporting holes from the anode 2 side to the light emitting layer 5 side is usually called a hole injection transport layer or a hole transport layer.
  • the layer closer to the anode side may be referred to as the hole injection layer 3.
  • the hole injection layer 3 is preferably formed in that it enhances the function of transporting holes from the anode 2 to the light emitting layer 5 side.
  • the hole injection layer 3 is usually formed on the anode 2.
  • the film thickness of the hole injection layer 3 is usually 1 nm or more, preferably 5 nm or more, usually 1000 nm or less, and preferably 500 nm or less.
  • the hole injection layer may be formed by either a vacuum vapor deposition method or a wet film deposition method. From the viewpoint of excellent film forming property, it is preferable to form by a wet film forming method.
  • the hole injection layer is preferably formed by a wet film forming method using a composition for forming a hole injection layer.
  • the composition for forming a hole injection layer usually contains a hole transporting compound that becomes the hole injection layer 3.
  • the composition for forming a hole injection layer usually further contains a solvent. It is preferable that the composition for forming a hole injection layer has high hole transportability and can efficiently transport the injected holes. Therefore, it is preferable that the hole mobility is high and impurities that serve as traps are unlikely to be generated during manufacturing or use. Further, it is preferable that the stability is excellent, the ionization potential is small, and the transparency to visible light is high. In particular, when the hole injection layer is in contact with the light emitting layer, those that do not quench the light emitted from the light emitting layer or those that form an exciplex with the light emitting layer and do not reduce the luminous efficiency are preferable.
  • hole transporting compound a compound having an ionization potential of 4.5 eV to 6.0 eV is preferable from the viewpoint of a charge injection barrier from the anode to the hole injection layer.
  • hole-transporting compounds include aromatic amine compounds, phthalocyanine compounds, porphyrin compounds, oligothiophene compounds, polythiophene compounds, benzylphenyl compounds, compounds in which a tertiary amine is linked with a fluorene group, and hydrazone.
  • examples thereof include a system compound, a silazane system compound, and a quinacridone system compound.
  • aromatic amine compounds are preferable, and aromatic tertiary amine compounds are particularly preferable, from the viewpoint of amorphousness and visible light transmission.
  • the aromatic tertiary amine compound is a compound having an aromatic tertiary amine structure, and also includes a compound having a group derived from the aromatic tertiary amine.
  • the type of the aromatic tertiary amine compound is not particularly limited, but is a polymer compound having a weight average molecular weight of 1,000 or more and 1,000,000 or less (repeatedly) because it is easy to obtain uniform light emission due to the surface smoothing effect. It is preferable to use a polymerized compound in which the units are continuous.
  • the hole injection layer 3 is formed by the wet film formation method
  • the material to be the hole injection layer is usually mixed with a soluble solvent (solvent for the hole injection layer) to form a composition for film formation (holes).
  • a composition for forming an injection layer is prepared.
  • the hole-injection layer forming composition is applied onto a layer (usually an anode) corresponding to the lower layer of the hole-injection layer to form a film, and the hole-injection layer 3 is formed by drying.
  • the concentration of the hole transporting compound in the composition for forming a hole injection layer is arbitrary as long as the effect of the present invention is not significantly impaired, but a lower concentration is preferable in terms of film thickness uniformity, and hole injection is preferable. Higher is preferable in that defects are less likely to occur in the layer. Specifically, it is preferably 0.01% by mass or more, further preferably 0.1% by mass or more, particularly preferably 0.5% by mass or more, and 70% by mass or less. Is more preferable, and it is more preferably 60% by mass or less, and particularly preferably 50% by mass or less.
  • solvent examples include ether solvents, ester solvents, aromatic hydrocarbon solvents, amide solvents and the like.
  • ether solvent examples include aliphatic ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether and propylene glycol-1-monomethyl ether acetate (PGMEA), and 1,2-dimethoxybenzene, 1,3-dimethoxybenzene and anisole. , Fenetol, 2-methoxytoluene, 3-methoxytoluene, 4-methoxytoluene, 2,3-dimethylanisole, 2,4-dimethylanisole and other aromatic ethers.
  • aliphatic ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether and propylene glycol-1-monomethyl ether acetate (PGMEA), and 1,2-dimethoxybenzene, 1,3-dimethoxybenzene and anisole.
  • PMEA propylene glycol-1-monomethyl ether acetate
  • Fenetol 2-methoxytoluene
  • ester-based solvent examples include aromatic esters such as phenyl acetate, phenyl propionate, methyl benzoate, ethyl benzoate, propyl benzoate, and n-butyl benzoate.
  • aromatic hydrocarbon solvent examples include toluene, xylene, cyclohexylbenzene, 3-isopropylbiphenyl, 1,2,3,4-tetramethylbenzene, 1,4-diisopropylbenzene, cyclohexylbenzene, methylnaphthalene and the like. Be done.
  • amide-based solvent examples include N, N-dimethylformamide, N, N-dimethylacetamide and the like.
  • dimethyl sulfoxide and the like can also be used.
  • the formation of the hole injection layer 3 by the wet film formation method is usually performed on the layer corresponding to the lower layer of the hole injection layer 3 (usually, the anode 2) after preparing the composition for forming the hole injection layer. It is carried out by applying a film to the film and drying it. In the hole injection layer 3, the coating film is usually dried by heating, vacuum drying, or the like after the film formation.
  • the hole injection layer 3 is formed by the vacuum vapor deposition method
  • a crucible installed in a vacuum vessel (two or more kinds of materials).
  • the crucible is heated (when two or more kinds of materials are used, each crucible is usually heated), and the material in the crucible is evaporated while controlling the evaporation amount (when two or more kinds of materials are used).
  • a mixture thereof can be placed in a crucible and heated and evaporated to form a hole injection layer.
  • the degree of vacuum at the time of vapor deposition is not limited as long as the effect of the present invention is not significantly impaired, but is usually 0.1 ⁇ 10 -6 Torr (0.13 ⁇ 10 -4 Pa) or more, 9.0 ⁇ 10 -6 Torr ( 12.0 ⁇ 10 -4 Pa) or less.
  • the vapor deposition rate is not limited as long as the effect of the present invention is not significantly impaired, but is usually 0.1 ⁇ / sec or more and 5.0 ⁇ / sec or less.
  • the film formation temperature at the time of vapor deposition is not limited as long as the effect of the present invention is not significantly impaired, but is preferably 10 ° C. or higher and 50 ° C. or lower.
  • the hole injection layer 3 may be crosslinked.
  • the hole transport layer 4 is a layer having a function of transporting holes from the anode 2 side to the light emitting layer 5 side.
  • the hole transport layer 4 is preferably formed in the organic electroluminescent device of the present invention in terms of enhancing the function of transporting holes from the anode 2 to the light emitting layer 5.
  • the hole transport layer 4 is usually formed between the anode 2 and the light emitting layer 5.
  • the hole transport layer 4 is formed between the hole injection layer 3 and the light emitting layer 5.
  • the film thickness of the hole transport layer 4 is usually 5 nm or more, preferably 10 nm or more, and usually 300 nm or less, preferably 100 nm or less.
  • the hole transport layer 4 may be formed by either a vacuum vapor deposition method or a wet film deposition method. From the viewpoint of excellent film forming property, it is preferable to form by a wet film forming method.
  • the hole transport layer is preferably formed by a wet film forming method using the above-mentioned second composition as the composition for forming the hole transport layer.
  • the hole transport layer 4 usually contains a hole transport compound.
  • the hole transporting compound contained in the hole transporting layer 4 the second polymer contained in the second organic layer is preferable.
  • two or more tertiary amines represented by the hole transporting compound 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl, can be used.
  • Stars such as aromatic diamine (Japanese Patent Laid-Open No. 5-234681) in which two or more condensed aromatic rings are substituted with nitrogen atoms, 4,4', 4 "-tris (1-naphthylphenylamino) triphenylamine and the like.
  • Aromatic amine compounds with a burst structure J. Lumin., 72-74, pp.
  • hole transport layer is formed by the wet film forming method
  • holes are usually formed instead of the hole injection layer forming composition in the same manner as in the case where the hole injection layer is formed by the wet film forming method. It is formed using a composition for forming a transport layer.
  • the composition for forming the hole transport layer usually further contains a solvent.
  • a solvent used in the composition for forming a hole transport layer, the same solvent as the solvent used in the composition for forming a hole injection layer described above can be used.
  • the concentration of the hole-transporting compound in the composition for forming the hole-transporting layer can be in the same range as the concentration of the hole-transporting compound in the composition for forming the hole-injecting layer.
  • the hole transport layer can be formed by the wet film formation method in the same manner as the hole injection layer film formation method described above.
  • the hole transport is usually performed instead of the composition for forming the hole injection layer in the same manner as in the case of forming the hole injection layer by the vacuum vapor deposition method. It can be formed using a layer-forming composition.
  • the film formation conditions such as the degree of vacuum, the vapor deposition rate, and the temperature at the time of vapor deposition can be the same as those at the time of vacuum deposition of the hole injection layer.
  • the light emitting layer 5 is a layer having a function of emitting light by being excited by recombination of holes injected from the anode 2 and electrons injected from the cathode 7 when an electric field is applied between the pair of electrodes. ..
  • the light emitting layer 5 is a layer formed between the anode 2 and the cathode 7.
  • the light emitting layer is formed between the hole injection layer and the cathode when there is a hole injection layer on the anode.
  • the light emitting layer 5 is formed between the hole transport layer and the cathode.
  • the organic electroluminescent device in the present invention contains the polycyclic heterocyclic compound represented by the above formula (1) as a light emitting material, and the above compound I, the said compound II, the said compound III, and the said compound IV as host materials. It is preferable to have a light emitting layer containing at least one kind. Further, since the host material preferably contains a material having electron transporting property and a material having hole transporting property, the host material is represented by the formula (30) which is the second host material as the electron transporting host material. It is preferable that the compound and at least one of the compound II are contained, and at least one of the compound III and the compound IV is contained as the hole transporting host material.
  • the preferable compounding ratio (mass ratio) when the light emitting layer of the organic electroluminescent element of the present invention contains the compound represented by the above formula (30) as the second host is as follows.
  • the blending amount of the compound I with respect to the total of 100 of the compound represented by the formula (30) and the compound I is preferably 50 or less, more preferably 40 or less, further preferably 30 or less, and particularly preferably 25 or less. 5 or more is preferable, 10 or more is more preferable, and 20 or more is particularly preferable.
  • the blending amount of the compound II with respect to the total of 100 of the compound represented by the formula (30) and the compound II is preferably 30 or less, more preferably 20 or less, still more preferably 10 or less, and particularly preferably 5 or less.
  • the blending amount of the compound III with respect to the total of 100 of the compound represented by the formula (30) and the compound III is preferably 30 or less, more preferably 20 or less, still more preferably 10 or less, and particularly preferably 5 or less.
  • 1 or more is preferable, and 3 or more is more preferable.
  • the blending amount of the compound IV with respect to the total of 100 of the compound represented by the formula (30) and the compound IV is preferably 70 or less, more preferably 50 or less, particularly preferably 30 or less, and most preferably 20 or less. 1 or more is preferable, 3 or more is more preferable, and 5 or more is particularly preferable.
  • the compound II is contained and the compound III or the compound IV is contained, and the compound II and the compound IV are contained. Is more preferable.
  • the compounding ratio (mass ratio) when the compound II is contained and the compound III or the compound IV is contained is the said in terms of the compounding amount of the compound II and the compounding amount of the compound III or the compound IV to a total of 100.
  • the blending amount of compound II is preferably 10 or more, more preferably 30 or more, particularly preferably 50 or more, most preferably 70 or more, preferably 95 or less, further preferably 90 or less, and particularly preferably 85 or less.
  • the film thickness of the light emitting layer 5 is arbitrary as long as the effect of the present invention is not significantly impaired.
  • the film thickness of the light emitting layer 5 is preferably 3 nm or more, more preferably 5 nm or more, preferably 200 nm or less, and further preferably 100 nm or less.
  • the light emitting layer 5 contains at least a material having light emitting properties (light emitting material), and preferably contains one or more host materials.
  • the host material is usually a charge transport material, but a material having a low charge transport property may be blended in order to adjust the charge transport property.
  • the light emitting layer may be formed by either a vacuum vapor deposition method or a wet film forming method, but the wet film forming method is preferable, and the spin coating method and the inkjet method are more preferable because of the excellent film forming property.
  • a light emitting layer is formed using the composition for forming a light emitting layer of the present invention, laminating by a wet film forming method is easy, so that it is preferable to adopt a wet film forming method.
  • the hole injection layer is formed with the light emitting layer instead of the composition for forming the hole injection layer in the same manner as in the case of forming the hole injection layer by the wet film forming method.
  • the material is formed by using a composition for forming a light emitting layer prepared by mixing a soluble solvent (solvent for a light emitting layer).
  • the solvent examples include ether-based solvents, ester-based solvents, aromatic hydrocarbon-based solvents, amide-based solvents, alcan-based solvents, halogenated aromatic hydrocarbon-based solvents, and fats mentioned for the formation of the hole injection layer.
  • examples thereof include a group alcohol solvent, an alicyclic alcohol solvent, an aliphatic ketone solvent, an alicyclic ketone solvent and the like. Specific examples of the solvent are given below, but the present invention is not limited thereto as long as the effect of the present invention is not impaired.
  • aliphatic ether solvents such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol-1-monomethyl ether acetate (PGMEA); 1,2-dimethoxybenzene, 1,3-dimethoxybenzene, anisole, phenetol, 2 -Aromatic ether solvents such as methoxytoluene, 3-methoxytoluene, 4-methoxytoluene, 2,3-dimethylanisole, 2,4-dimethylanisole, diphenyl ether; phenyl acetate, phenyl propionate, methyl benzoate, benzoic acid Aromatic ester solvents such as ethyl, propyl benzoate, n-butyl benzoate; toluene, xylene, mesitylen, cyclohexylbenzene, tetralin, 3-isopropylbiphenyl, 1,2,3,
  • a hole blocking layer may be provided between the light emitting layer 5 and the electron transport layer 6 described later.
  • the hole blocking layer is a layer laminated on the light emitting layer 5 so as to be in contact with the interface on the cathode 7 side of the light emitting layer 5.
  • This hole blocking layer has a role of blocking holes moving from the anode 2 from reaching the cathode 7 and a role of efficiently transporting electrons injected from the cathode 7 toward the light emitting layer 5.
  • the physical properties required for the material constituting the hole blocking layer are high electron mobility and low hole mobility, a large energy gap (difference between HOMO and LUMO), and an excited triplet level (T 1 ). Is high.
  • Examples of the material of the hole blocking layer satisfying such conditions include bis (2-methyl-8-quinolinolato) (phenorato) aluminum, bis (2-methyl-8-quinolinolato) (triphenylsilanorat) aluminum and the like.
  • Mixed ligand complex bis (2-methyl-8-quinolato) aluminum- ⁇ -oxo-bis- (2-methyl-8-quinolilato) aluminum dinuclear metal complex and other metal complexes, distyrylbiphenyl derivative and the like.
  • Triazole derivatives such as styryl compounds (Japanese Patent Laid-Open No.
  • the hole blocking layer There are no restrictions on the method of forming the hole blocking layer. Therefore, it can be formed by a wet film forming method, a thin film deposition method, or another method.
  • the film thickness of the hole blocking layer is arbitrary as long as the effect of the present invention is not significantly impaired, but is usually 0.3 nm or more, preferably 0.5 nm or more, and usually 100 nm or less, preferably 50 nm or less.
  • the electron transport layer 6 is provided between the light emitting layer 5 and the cathode 7 for the purpose of further improving the current efficiency of the device.
  • the electron transport layer 6 is formed of a compound capable of efficiently transporting electrons injected from the cathode 7 between electrodes to which an electric field is applied in the direction of the light emitting layer 5.
  • the electron transporting compound used in the electron transporting layer 6 is a compound having high electron injection efficiency from the cathode 7, high electron mobility, and capable of efficiently transporting the injected electrons. is required.
  • Examples of the electron-transporting compound used in the electron-transporting layer include a metal complex such as an aluminum complex of 8-hydroxyquinoline (Japanese Patent Laid-Open No. 59-194393), a metal complex of 10-hydroxybenzo [h] quinoline, and oxadi.
  • phenanthroline derivative Japanese Patent Laid-Open No. 5-331459
  • 2-tert-butyl-9,10-N, N'-dicyanoanthraquinonediimine n-type hydrogenated amorphous Examples thereof include silicon carbide, n-type zinc sulfide, and n-type zinc selenium.
  • the film thickness of the electron transport layer 6 is usually 1 nm or more, preferably 5 nm or more, and usually 300 nm or less, preferably 100 nm or less.
  • the electron transport layer 6 is formed by laminating on a light emitting layer or a hole blocking layer by a wet film forming method or a vacuum vapor deposition method in the same manner as described above. Usually, a vacuum deposition method is used.
  • an electron injection layer may be provided between the electron transport layer 6 and the cathode 7.
  • the material forming the electron injection layer is preferably a metal having a low work function.
  • an alkali metal such as sodium or cesium, an alkaline earth metal such as barium or calcium, or the like is used.
  • the film thickness is usually preferably 0.1 nm or more and 5 nm or less.
  • an organic electron transport material represented by a nitrogen-containing heterocyclic compound such as vasophenantroline and a metal complex such as an aluminum complex of 8-hydroxyquinoline is doped with an alkali metal such as sodium, potassium, cesium, lithium and rubidium (). Also described in JP-A No. 10-270171, JP-A-2002-100478, JP-A-2002-1000482, etc.), because electron injection and transportability are improved and excellent film quality can be achieved at the same time. preferable.
  • the film thickness of the electron injection layer is usually 5 nm or more, preferably 10 nm or more, and usually 200 nm or less, preferably 100 nm or less.
  • the electron injection layer is formed by laminating on the light emitting layer 5 or the hole blocking layer or the electron transport layer 6 on the light emitting layer 5 by a wet film forming method or a vacuum vapor deposition method.
  • the details of the wet film forming method are the same as those of the above-mentioned light emitting layer.
  • the hole blocking layer, electron transport layer, and electron injection layer may be made into one layer by the operation of electron transport material and lithium complex co-doping.
  • the cathode 7 plays a role of injecting electrons into a layer on the light emitting layer 5 side (electron injection layer, light emitting layer, or the like).
  • the material used for the anode 2 can be used.
  • a metal having a low work function in order to efficiently inject electrons, and for example, a metal such as tin, magnesium, indium, calcium, aluminum, silver or an alloy thereof is used. Be done.
  • Specific examples include alloy electrodes having a low work function such as magnesium-silver alloys, magnesium-indium alloys, and aluminum-lithium alloys.
  • the organic electroluminescent element it is preferable to laminate a metal layer having a high work function and stable with respect to the atmosphere on the cathode to protect the cathode made of a metal having a low work function.
  • the metal to be laminated include metals such as aluminum, silver, copper, nickel, chromium, gold, and platinum.
  • the film thickness of the cathode is usually the same as that of the anode.
  • the organic electroluminescent device of the present invention may further have another layer as long as the effect of the present invention is not significantly impaired. Any other layer may be provided between the anode and the cathode.
  • the organic electroluminescent device of the present invention has a structure opposite to that described above, that is, for example, a cathode, an electron injection layer, an electron transport layer, a hole blocking layer, a light emitting layer, a hole transport layer, and holes on a substrate. It is also possible to stack the injection layer and the anode in this order.
  • the organic electroluminescent device of the present invention When the organic electroluminescent device of the present invention is applied to an organic electroluminescent device, it may be used as a single organic electroluminescent device or may be used in a configuration in which a plurality of organic electroluminescent devices are arranged in an array.
  • the anode and cathode may be arranged in an XY matrix.
  • the organic EL display device (organic electroluminescent element display device) of the present invention includes the organic electroluminescent element of the present invention.
  • the model and structure of the organic EL display device of the present invention are not particularly limited, and can be assembled according to a conventional method using the organic electroluminescent device of the present invention.
  • the organic EL display device of the present invention can be obtained by a method as described in "Organic EL Display” (Ohmsha, published on August 20, 2004, by Shizushi Tokito, Chihaya Adachi, Hideyuki Murata). Can be formed.
  • the organic EL lighting (organic electroluminescent element lighting) of the present invention includes the organic electroluminescent element of the present invention.
  • the type and structure of the organic EL lighting of the present invention are not particularly limited, and can be assembled according to a conventional method using the organic electroluminescent device of the present invention.
  • the organic electroluminescent device manufactured by using the formula (D-1) described later as a light emitting material showed blue light emission having a peak wavelength of about 464 nm and a half width of about 30 nm. ..
  • Example I-1 An organic electroluminescent device was manufactured by the following method. A 2 mm wide stripe of indium tin oxide (ITO) transparent conductive film deposited on a glass substrate to a thickness of 50 nm (a sputtered film product manufactured by Geomatec Co., Ltd.) using ordinary photolithography technology and hydrochloric acid etching. The anode was formed by patterning. The substrate on which the ITO pattern is formed is washed in the order of ultrasonic cleaning with an aqueous solution of a surfactant, water washing with ultrapure water, ultrasonic cleaning with ultrapure water, and water washing with ultrapure water, and then dried with compressed air. Finally, UV ozone cleaning was performed.
  • ITO indium tin oxide
  • composition for forming a hole injection layer 3.0% by mass of a hole transporting polymer compound having a repeating structure of the following formula (P-1) and 0.6% by mass of an oxidizing agent (HI-1) are used. , A composition dissolved in ethyl benzoate was prepared.
  • This composition for forming a hole injection layer is spin-coated on the substrate in the atmosphere and dried on an atmospheric hot plate at 240 ° C. for 30 minutes to form a uniform thin film having a film thickness of 40 nm to form a hole injection layer. And said.
  • a charge-transporting polymer compound having the following structural formula (HT-1) was dissolved in cyclohexylbenzene at a concentration of 3.0% by mass to prepare a composition for forming a hole transport layer.
  • This composition for forming a hole transport layer is spin-coated in a nitrogen glove box on a substrate coated with the hole injection layer and dried at 230 ° C. for 30 minutes on a hot plate in the nitrogen glove box to form a film.
  • a uniform thin film having a thickness of 40 nm was formed to form a hole transport layer.
  • This composition for forming a light emitting layer is spin-coated in a nitrogen glove box on a substrate coated with the hole transport layer, dried at 120 ° C. for 20 minutes on a hot plate in the nitrogen glove box, and has a film thickness of 40 nm. A uniform thin film was formed to form a light emitting layer.
  • the substrate on which the film was formed up to the light emitting layer was installed in a vacuum vapor deposition apparatus, and the inside of the apparatus was exhausted until it became 2 ⁇ 10 -4 Pa or less.
  • a 2 mm wide striped shadow mask as a mask for cathode vapor deposition is brought into close contact with the substrate so as to be orthogonal to the ITO stripe of the anode, and aluminum is heated by a molybdenum boat to form an aluminum layer having a thickness of 80 nm. Formed to form a cathode.
  • an organic electroluminescent device having a light emitting area portion having a size of 2 mm ⁇ 2 mm was obtained.
  • composition of the light emitting layer forming composition is the same as that of Example I-1 except that (H-1) is 97 parts by mass, (D-1) is 3 parts by mass, and (H-2) is not used. The element was manufactured.
  • Example II-1 As the material of the light emitting layer, 92 parts by mass of the following structural formula (H-1), 5 parts by mass of (H-3), and 3 parts by mass of (D-1) are weighed and dissolved in cyclohexylbenzene to have a solid content concentration. A 4.2% by mass solution was prepared and used as a composition for forming a light emitting layer.
  • the device was produced in the same manner as in Example I-1 except that the above light emitting layer forming composition was used as the light emitting layer forming composition.
  • Table 2 shows the voltage difference (V) obtained by subtracting the voltage of Comparative Example 1 from Example II-1, the relative current luminous efficiency of Example II-1 when the current luminous efficiency of Comparative Example 1 is 1, and the comparative example.
  • Example II-2 As the material of the light emitting layer, it is carried out except that the structural formula (H-1) is 92 parts by mass, the following structural formula (H-6) is 5 parts by mass, and the structural formula (D-1) is 3 parts by mass.
  • the element was manufactured in the same manner as in Example II-1.
  • Example II-3 As the material of the light emitting layer, it is carried out except that the structural formula (H-1) is 92 parts by mass, the following structural formula (H-7) is 5 parts by mass, and the structural formula (D-1) is 3 parts by mass.
  • the element was manufactured in the same manner as in Example II-1.
  • Table 3 shows the relative current luminous efficiency of Example II-2 when the current luminous efficiency of Comparative Example 1 is 1, and the external quantum efficiency (EQE) of Comparative Example 1 of Example II-2.
  • Table 4 shows the voltage difference (V) obtained by subtracting the voltage of Comparative Example 1 from Example II-3, and the relative current luminous efficiency of Example II-3 when the current luminous efficiency of Comparative Example 1 is 1.
  • V voltage difference
  • EQE external quantum efficiency
  • the organic electroluminescent device of the present invention using compound II as the first host material is expected to have high luminous efficiency, low voltage and long life, and the device performance is improved. I found out that I would do it.
  • Example III-1 As the material of the light emitting layer, the following structural formula (H-1) is 92 parts by mass, (H-4) is 5 parts by mass, and (D-1) is 3 parts by mass. The element was manufactured in the same manner.
  • Example III-2 An element was produced in the same manner as in Example III-1 except that (H-5) having the following structure was used instead of (H-4) as the material of the light emitting layer.
  • Table 5 shows the voltage difference (V) obtained by subtracting the voltage of Comparative Example 1 from Example III-1 and Example III-2, and Examples III-1 and Implementation when the current luminous efficiency of Comparative Example 1 is 1.
  • the relative EQE of Example III-1 and Example III-2 is described when the relative current luminous efficiency of Example III-2 and the external quantum efficiency (EQE) of Comparative Example 1 are set to 1.
  • the organic electroluminescent device of the present invention using compound III as the first host material has high luminous efficiency and improved device performance with low voltage drive. Further, when the elements obtained in Example III-1 and Comparative Example 1 are continuously energized with a current density of 20 mA / cm 2 , the time (hr) in which the brightness of the element decreases to 90% of the initial brightness is set. When measured as the life, the relative life of Example III-1 was 1.39 when the life of Comparative Example 1 was 1, indicating that the life was extended.
  • the element was manufactured in the same manner as in 2.
  • Comparative Example III-2 As the material of the light emitting layer, an element was manufactured in the same manner as in Comparative Example III-1 except that the formula (H-1) was 97 parts by mass and the formula (D-2) was 3 parts by mass.
  • Example IV-1 Examples I-1 as the material of the light emitting layer, except that the formula (H-1) is 92 parts by mass, the following formula (H-8) is 5 parts by mass, and the formula (D-1) is 3 parts by mass. The element was manufactured in the same manner as above.
  • Table 6 shows the voltage difference (V) obtained by subtracting the voltage of Comparative Example 1 from Example IV-1, the relative current luminous efficiency of Example IV-1 when the current luminous efficiency of Comparative Example 1 is 1, and the comparative example.
  • Example 1 a polymer having no cross-linking group was used as the second polymer forming the hole transport layer.
  • An organic electroluminescent device containing compound II and compound IV was produced as a host material for the light emitting layer.
  • the following formula (HT-2) is used instead of the above formula (HT-1).
  • the following formula (H-9) is 22.5 parts by mass
  • the following formula (H-10) is 22.5 parts by mass
  • the above formula (H-8) is 15 parts by mass
  • the following formula (D) is used as the material of the light emitting layer.
  • Example I-3 was weighed in 3 parts by mass, dissolved in cyclohexylbenzene to prepare a solution having a solid content concentration of 4.2% by mass, and the same as in Example I-1 except that the composition was prepared as a composition for forming a light emitting layer.
  • the element was manufactured.
  • Example 2 Organic electroluminescence is carried out in the same manner as in Example 1 except that the structural formula (HT-3) is used instead of the compound represented by the structural formula (HT-2) as the material of the hole transport layer. The element was manufactured.
  • Example 3 Organic electroluminescence is carried out in the same manner as in Example 1 except that the structural formula (HT-1) is used instead of the compound represented by the structural formula (HT-2) as the material of the hole transport layer. The element was manufactured.
  • Table 7 shows the voltage difference (V) obtained by subtracting the voltage of Example 3 from Example 1 and Example 2, and the relative current emission of Examples 1 and 2 when the current luminous efficiency of Example 3 is 1. Efficiency, relative EQE of Examples 1 and 2 when the external quantum efficiency (EQE) of Example 3 is 1, and relative of Examples 1 and 2 when the lifetime of Example is 1. I wrote down the life.
  • the present invention relates to various fields in which an organic electroluminescent element is used, for example, a flat panel display (for example, for an OA computer or a wall-mounted television), or a light source that takes advantage of its characteristics as a surface emitter (for example, a light source for a copying machine).
  • a flat panel display for example, for an OA computer or a wall-mounted television
  • a light source that takes advantage of its characteristics as a surface emitter
  • Liquid crystal display, backlight source of instruments), display board, indicator light, etc. can be suitably used.

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Abstract

L'invention concerne une composition pour former une couche luminescente d'un élément électroluminescent organique qui comprend un composé hétérocyclique polycyclique représenté par la formule (1), un composé représenté par la formule (20), et un solvant organique. L'invention concerne un élément électroluminescent organique ayant une longue durée de vie qui a une couche luminescente contenant un composé hétérocyclique polycyclique qui contient du bore. (Le cycle a, le cycle b et le cycle c sont des cycles hydrocarbonés aromatiques ou des hétérocycles aromatiques. Y est O, N-R ou S. R est un groupe cyclique hydrocarboné aromatique, un groupe hétérocyclique aromatique ou un groupe alkyle. R peut se lier avec un atome de carbone adjacent à un atome lié à Y dans au moins l'un des cycles a-c par -O-, -S-, -C(-Ra)2-, ou une liaison simple. Ra représente un atome d'hydrogène ou un groupe alkyle.) (Ar21-Ar35 sont un atome d'hydrogène ou une structure dans laquelle une ou 2 à 10 structures cycliques de benzène sont non ramifiées ou ramifiées et liées.)
PCT/JP2021/047764 2020-12-24 2021-12-23 Composition pour former une couche luminescente d'un élément électroluminescent organique, élément électroluminescent organique, dispositif d'affichage électroluminescent organique et dispositif d'éclairage électroluminescent organique WO2022138790A1 (fr)

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JP2022571601A JPWO2022138790A1 (fr) 2020-12-24 2021-12-23
KR1020237020109A KR20230124575A (ko) 2020-12-24 2021-12-23 조성물, 유기 전계 발광 소자 및 그 제조 방법, 유기 전계 발광 표시 장치 및 그 제조 방법, 유기 전계 발광 조명 및 그 제조 방법

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WO2019120125A1 (fr) * 2017-12-21 2019-06-27 广州华睿光电材料有限公司 Composition pour la préparation d'un dispositif électronique organique, dispositif électronique organique et application associée
WO2020040298A1 (fr) * 2018-08-23 2020-02-27 学校法人関西学院 Élément électroluminescent organique, dispositif d'affichage, dispositif d'éclairage, composition de formation de couche luminescente et composé
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EP3522248B1 (fr) 2016-09-29 2023-08-09 Sumitomo Chemical Company Limited Élément électroluminescent et composition servant à la fabrication de l'élément électroluminescent
KR20190132645A (ko) 2017-04-03 2019-11-28 이데미쓰 고산 가부시키가이샤 유기 전기발광 소자 및 전자 기기
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JP2019057484A (ja) * 2017-09-22 2019-04-11 三菱ケミカル株式会社 有機電界発光素子、有機電界発光素子の製造方法
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WO2024090353A1 (fr) * 2022-10-27 2024-05-02 東レ株式会社 Composé, matériau d'élément luminescent, élément luminescent, dispositif d'affichage et illuminateur

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