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WO2024117109A1 - Composition pour former une couche électroluminescente d'élément électroluminescent organique, élément électroluminescent organique et son procédé de production, et dispositif d'affichage - Google Patents

Composition pour former une couche électroluminescente d'élément électroluminescent organique, élément électroluminescent organique et son procédé de production, et dispositif d'affichage Download PDF

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WO2024117109A1
WO2024117109A1 PCT/JP2023/042479 JP2023042479W WO2024117109A1 WO 2024117109 A1 WO2024117109 A1 WO 2024117109A1 JP 2023042479 W JP2023042479 W JP 2023042479W WO 2024117109 A1 WO2024117109 A1 WO 2024117109A1
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奈良 麻優子 上田
一毅 岡部
英貴 五郎丸
延軍 李
司 長谷川
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Mitsubishi Chemical Corp
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10—Deposition of organic active material
    • H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
    • 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
    • H10K85/30—Coordination compounds
    • 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
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission

Definitions

  • the present invention relates to a composition for forming a light-emitting layer of an organic electroluminescent element (hereinafter, sometimes referred to as "composition for forming a light-emitting layer”) that is useful for forming a light-emitting layer of an organic electroluminescent element (hereinafter, sometimes referred to as "organic EL element”).
  • composition for forming a light-emitting layer an organic electroluminescent element
  • organic EL element organic electroluminescent element
  • Organic electroluminescent elements consume little power due to the low applied voltage, and are capable of emitting the three primary colors, so they are beginning to be used not only in large display monitors, but also in small and medium-sized displays such as mobile phones and smartphones.
  • Organic electroluminescent devices are manufactured by stacking multiple layers, including a light-emitting layer, a charge injection layer, and a charge transport layer.
  • a light-emitting layer a charge injection layer
  • a charge transport layer a charge transport layer.
  • organic electroluminescent devices are manufactured by depositing organic materials under vacuum, but the vacuum deposition method requires a complicated deposition process and is poor in productivity. In addition, it is extremely difficult to enlarge the panels of lighting or displays using organic electroluminescent devices manufactured by the vacuum deposition method.
  • wet film formation has been researched as a process for efficiently manufacturing organic electroluminescent elements that can be used in large displays and lighting.
  • the wet film formation method has the advantage of being able to easily form stable layers compared to the vacuum deposition method, so it is expected to be used in the mass production of displays and lighting devices and in large devices.
  • Patent Document 1 discloses an organic electroluminescent device in which a light-emitting layer containing a compound having a biscarbazole skeleton as shown below is formed by a vacuum deposition method, and attempts are made to improve the driving voltage and efficiency.
  • Patent Document 2 discloses an organic electroluminescent device in which a light-emitting layer containing a compound containing a biscarbazole skeleton as shown below is formed by a wet film-forming method, and attempts are made to provide a composition for forming a light-emitting layer for an organic electroluminescent device that has excellent solubility in organic solvents.
  • An object of the present invention is to provide a composition for forming a light-emitting layer for producing an organic electroluminescent device which can be produced preferably by a wet film-forming method and has higher light-emitting efficiency than conventional devices.
  • a light-emitting layer preferably by a wet film-forming method, using a composition for forming a light-emitting layer that contains a heteroaromatic ring compound of a specific structure and an indolocarbazole compound of a specific structure, and further contains a light-emitting material and an organic solvent, and thus arrived at the present invention.
  • the gist of the present invention is as follows:
  • composition for forming a light-emitting layer of an organic electroluminescent device contains at least a compound represented by formula (1), a compound represented by formula (2), a light-emitting material, and an organic solvent.
  • Each W independently represents CH or N, and at least one W is N;
  • Xa 1 , Ya 1 , and Za 1 each independently represent a divalent aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, or a divalent aromatic heterocyclic group having 3 to 30 carbon atoms which may have a substituent, and when there are a plurality of Xa 1 , Ya 1 , and Za 1 , they may be the same or different,
  • Xa 2 , Ya 2 and Za 2 each independently represent a hydrogen atom, a monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, or a monovalent aromatic heterocyclic group having 3 to 30 carbon atoms which may have a substituent;
  • 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, When g11 is 2 or more, the multiple Xa1 '
  • Ar 1 is a structure represented by formula (2a).
  • Each Ar2 is independently a (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent. When there are a plurality of Ar2 's, they may be the same or different.
  • Each R is independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a (hetero)aralkyl group having 7 to 40 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a (hetero)aryloxy group having 3 to 20 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an arylamino group having 6 to 20 carbon atoms, or a (hetero)aryl group having 3 to 30 carbon atoms.
  • These groups, except for the hydrogen atom may have a substituent.
  • At least one pair of adjacent Rs has a structure represented by formula (2b).
  • the subscripts m and n each independently represent an integer from 1 to 3.
  • Each R 1 is independently a hydrogen atom, a (hetero)aryl group having 3 to 20 carbon atoms which may have a substituent, or a bond to Ar 2 .
  • Ar3 is a (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent.
  • Each R2 is independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a (hetero)aralkyl group having 7 to 40 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a (hetero)aryloxy group having 3 to 20 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an arylamino group having 6 to 20 carbon atoms, or a (hetero)aryl group having 3 to 30 carbon atoms.
  • These groups, except for the hydrogen atom may have a substituent.
  • " ⁇ " indicates the bonding position with formula (2).
  • Aspect 2 of the present invention is in the composition for forming a light-emitting layer according to embodiment 1, the formula (1) is represented by the following formula (1-1):
  • W 1 , W 2 and W 3 each independently represent -CH or a nitrogen atom, and at least one of W 1 , W 2 and W 3 is a nitrogen atom;
  • Xa 1 , Ya 1 , and Za 1 each independently represent a 1,3-phenylene group which may have a substituent or a 1,4-phenylene group which may have a substituent, and when a plurality of Xa 1 , Ya 1 , and Za 1 are present, they may be the same or different, At least one of Za 1 is a 1,3-phenylene group;
  • Xa2 and Ya2 each independently represent a phenyl group which may have a substituent;
  • Za2 represents an N-carbazolyl group which may have a substituent.
  • f11 is 1 or 2;
  • g11 is an integer from 1 to 5, h11 is an integer from 2 to 5, j11 is an integer from 1 to 6,
  • Each R 11 independently represents a hydrogen atom or a substituent.
  • Aspect 3 of the present invention is in the composition for forming a light-emitting layer according to embodiment 1, the formula (1) is represented by the following formula (1-2):
  • W 1 , W 2 and W 3 each independently represent -CH or a nitrogen atom, and at least one of W 1 , W 2 and W 3 is a nitrogen atom;
  • Xa 1 , Ya 1 , and Za 1 each independently represent a 1,3-phenylene group which may have a substituent or a 1,4-phenylene group which may have a substituent, and when a plurality of Xa 1 , Ya 1 , and Za 1 are present, they may be the same or different, At least one of Ya1 and Za1 is a 1,3-phenylene group which may have a substituent;
  • Xa2 represents a phenyl group which may have a substituent;
  • Ya2 and Za2 each independently represent an N-carbazolyl group which may have a substituent;
  • f11 is 1 or 2;
  • g11 is an integer from 1 to 5,
  • h11 is an integer from 2 to 5,
  • j11 is an integer from 2 to 5,
  • Each R 11 independently
  • Aspect 4 of the present invention is in the composition for forming a light-emitting layer according to embodiment 3, at least one Ya 1 in the formula (1-2) is a 1,3-phenylene group, and at least one Za 1 is a 1,3-phenylene group.
  • Aspect 5 of the present invention is in the composition for forming a light-emitting layer according to embodiment 3 or 4, at least one of Xa 1 in formula (1-2) is a 1,3-phenylene group.
  • Aspect 6 of the present invention is The composition for forming an emission layer according to any one of Aspects 1 to 5, wherein the substituents which R 1 , R 2 , Ar 2 and Ar 3 in formula (2) may have are an alkyl group, an aralkyl group, a heteroaralkyl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylsilyl group, an arylsilyl group, an alkylcarbonyl group, an arylcarbonyl group, an alkylamino group, an arylamino group, an aryl group, or a heteroaryl group.
  • Aspect 7 of the present invention is The composition for forming a light-emitting layer according to any one of Aspects 1 to 5, wherein the formula (2) is represented by the following formula (2-1):
  • Ar 4 is a structure represented by the formula (2a)
  • Ar 5 is a group selected from the same groups as Ar 2 in the formula (2)
  • Ar 6 is a group selected from the same groups as Ar 3 in the formula (2b)
  • R 3 is each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a (hetero)aralkyl group having 7 to 40 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a (hetero)aryloxy group having 3 to 20 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an arylamino group having 6 to 20 carbon atoms, or a (hetero)aryl group having 3 to 30 carbon atoms.
  • each Ar 5 is independently a 1,3-phenylene group or a 1,4-phenylene group.
  • composition for forming an emission layer according to embodiment 7 or 8, wherein the substituents which R 3 , Ar 5 , and Ar 6 in formula (2-1) may have are an alkyl group, an aralkyl group, a heteroaralkyl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylsilyl group, an arylsilyl group, an alkylcarbonyl group, an arylcarbonyl group, an alkylamino group, an arylamino group, an aryl group, or a heteroaryl group.
  • Aspect 10 of the present invention is The composition for forming a light-emitting layer according to any one of Aspects 1 to 9, wherein the light-emitting material is represented by the following formula (3):
  • ring A1 represents an aromatic hydrocarbon ring structure which may have a substituent or an aromatic heterocyclic structure which may have a substituent.
  • Ring A2 represents an aromatic heterocyclic structure which may have a substituent.
  • R 201 and R 202 each independently represent a structure represented by formula (b), and "*" represents a bonding position with ring A1 or ring A2.
  • R 201 and R 202 may be the same or different, and when a plurality of R 201 and R 202 are present, they may be the same or different.
  • Ar 201 and Ar 203 each independently represent an aromatic hydrocarbon ring structure which may have a substituent, or an aromatic heterocyclic structure which may have a substituent.
  • Ar 202 represents an aromatic hydrocarbon ring structure which may have a substituent, an aromatic heterocyclic structure which may have a substituent, or an aliphatic hydrocarbon structure which may have a substituent.
  • Ar 201 , Ar 202 and Ar 203 may be the same or different.
  • the substituents bonded to ring A1, the substituents bonded to ring A2, or the substituents bonded to ring A1 and the substituents bonded to ring A2 may be bonded to each other to form a ring.
  • B 201 -L 200 -B 202 represents an anionic bidentate ligand.
  • B 201 and B 202 each independently represent a carbon atom, an oxygen atom, or a nitrogen atom, and these atoms may be atoms constituting a ring.
  • L 200 represents a single bond, or an atomic group constituting a bidentate ligand together with B 201 and B 202.
  • B 201 -L 200 -B 202 When a plurality of B 201 -L 200 -B 202 are present, they may be the same or different.
  • i1 and i2 each independently represent an integer of 0 to 12
  • i3 represents an integer of 0 or more, the upper limit of which is the number that can be substituted for Ar 202
  • i4 represents an integer of 0 or more, the upper limit of which is the number that can be substituted for Ar 201
  • k1 and k2 each independently represent an integer of 0 or more, the upper limit of which is the number of groups that can be substituted on ring A1 and ring A2
  • z represents an integer of 1 to 3.
  • M represents a metal atom selected from Groups 7 to 11 of the periodic table.
  • Aspect 11 of the present invention is The composition for forming a light-emitting layer according to any one of Aspects 1 to 10 further comprises a compound represented by the following formula (4):
  • Ar 61 to Ar 65 each independently represent a hydrogen atom or a monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent
  • L 1 to L 5 each independently represent a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent, and when a plurality of L 1 to L 5 are present, they may be the same or different
  • Each R 60 independently represents a substituent.
  • n represents an integer from 0 to 10
  • a1 to a3 each independently represents an integer of 0 to 3
  • at least one of Ar 61 , Ar 62 , Ar 63 , Ar 64 , and at least one Ar 65 when n is 1 or more, is not a hydrogen atom.
  • Aspect 12 of the present invention is A method for producing an organic electroluminescence device, comprising the step of forming a light-emitting layer by a wet film-forming method using the composition for forming a light-emitting layer according to any one of Aspects 1 to 11.
  • Aspect 13 of the present invention is The organic electroluminescence device has a light-emitting layer formed using the composition for forming a light-emitting layer according to any one of Aspects 1 to 11.
  • Aspect 14 of the present invention is A display device having the organic electroluminescent device according to aspect 13.
  • Organic electroluminescent devices produced using the light-emitting layer-forming composition according to an embodiment of the present invention exhibit excellent device characteristics, and in particular, have high light-emitting efficiency.
  • FIG. 1 is a schematic cross-sectional view showing an example of the structure of an organic electroluminescent device according to an embodiment of the present invention.
  • compound (1) the compound represented by formula (1).
  • the (hetero)aralkyl group, the (hetero)aryloxy group, and the (hetero)aryl group respectively refer to an aralkyl group that may contain a heteroatom, an aryloxy group that may contain a heteroatom, and an aryl group that may contain a heteroatom.
  • the term "may contain a heteroatom” means that one or more carbon atoms among the carbon atoms forming the aryl skeleton in the main skeleton of the aralkyl group, the aryloxy group, or the aryl group may be substituted with a heteroatom.
  • heteroatom examples include a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, and a silicon atom, and among these, a nitrogen atom is preferred from the viewpoint of durability.
  • the term "(hetero)aryl group” is used to mean a monocyclic group, a fused 2- to 4-ring group, and a group in which a plurality of monocyclic and/or fused 2- to 4-ring groups are linked together.
  • the (hetero)aryl group represents an aryl group which may contain a heteroatom, that is, an aryl group or a heteroaryl group, where an aryl group is an aromatic hydrocarbon group and a heteroaryl group is an aromatic heterocyclic group.
  • composition for forming a light-emitting layer is a composition for forming a light-emitting layer of an organic electroluminescent element, and contains at least a compound represented by formula (1), a compound represented by formula (2), a light-emitting material, and an organic solvent.
  • the reason why the organic electroluminescent element prepared using the composition for forming a light-emitting layer according to an embodiment of the present invention exhibits high light-emitting efficiency is unclear, but is presumed to be as follows. Since compound (1) has high electron transportability, it is possible to efficiently transfer electrons to the light-emitting material.
  • compound (2) it is first possible to efficiently transfer holes to the light-emitting material.
  • the light-emitting layer formed using the composition for forming a light-emitting layer according to an embodiment of the present invention it is possible to appropriately adjust the balance of charges, and the excited state of the light-emitting material can be efficiently created, so it is presumed that high light-emitting efficiency can be obtained.
  • the light-emitting layer prepared by combining compound (1) and compound (2) suppresses the formation of excited dimers between the same compounds or exciplexes between different compounds in the light-emitting layer, compared to light-emitting layers prepared by conventional techniques.
  • the light-emitting layer produced by combining compound (1) and compound (2) has higher energy due to excited dimers between the same compounds or excited complexes between different compounds in the light-emitting layer, compared to light-emitting layers produced by conventional techniques. Since excited dimers and excited complexes have lower excitation energy than the excitation energy of the original compounds, they cause a decrease in luminous efficiency, but it is considered that an organic electroluminescent device exhibiting high luminous efficiency can be obtained by using a combination of compound (1) and compound (2) according to the embodiment of the present invention in the light-emitting layer.
  • Compound (2) is a compound represented by the following formula (2).
  • Ar 1 is a structure represented by formula (2a).
  • Each Ar2 is independently a (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent. When there are a plurality of Ar2 's, they may be the same or different.
  • Each R is independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a (hetero)aralkyl group having 7 to 40 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a (hetero)aryloxy group having 3 to 20 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an arylamino group having 6 to 20 carbon atoms, or a (hetero)aryl group having 3 to 30 carbon atoms.
  • These groups, except for the hydrogen atom may have a substituent.
  • At least one pair of adjacent Rs has a structure represented by formula (2b).
  • the subscripts m and n each independently represent an integer from 1 to 3.
  • Each R 1 is independently a hydrogen atom, a (hetero)aryl group having 3 to 20 carbon atoms which may have a substituent, or a bond to Ar 2 .
  • Ar3 is a (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent.
  • Each R2 is independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a (hetero)aralkyl group having 7 to 40 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a (hetero)aryloxy group having 3 to 20 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an arylamino group having 6 to 20 carbon atoms, or a (hetero)aryl group having 3 to 30 carbon atoms.
  • These groups, except for the hydrogen atom may have a substituent.
  • " ⁇ " indicates the bonding position with formula (2).
  • Ar 2 is preferably a (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent, and more preferably an aryl group having 6 to 60 carbon atoms.
  • Ar2 include divalent groups derived from a benzene ring, a naphthalene ring, a dibenzofuran ring, a thiophene ring, a dibenzothiophene ring, and a carbazole ring, and also divalent groups formed by bonding these together, such as a divalent group derived from phenylthiophene formed by bonding a benzene ring and a thiophene ring.
  • a benzene ring, a naphthalene ring, or a dibenzofuran ring is preferred, a benzene ring or a naphthalene ring is more preferred, and a divalent group derived from a benzene ring is particularly preferred.
  • the substituent which Ar2 may have is preferably a substituent selected from the substituent group Z described below.
  • Each R is independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a (hetero)aralkyl group having 7 to 40 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a (hetero)aryloxy group having 3 to 20 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an arylamino group having 6 to 20 carbon atoms, or a (hetero)aryl group having 3 to 30 carbon atoms.
  • a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a (hetero)aralkyl group having 7 to 40 carbon atoms, a (hetero)aryloxy group having 3 to 20 carbon atoms, an arylamino group having 6 to 20 carbon atoms, or a (hetero)aryl group having 3 to 30 carbon atoms is preferable, and a hydrogen atom or an aryl group having 3 to 30 carbon atoms is more preferable.
  • At least one pair of adjacent R's has a structure represented by formula (2b).
  • the substituent that R may have is preferably a substituent selected from the substituent group Z described below.
  • Examples of the alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a propyl group, a hexyl group, an octyl group, a decyl group, etc. From the viewpoint of element stability, a methyl group, an ethyl group, and a hexyl group are preferable, and a methyl group is more preferable.
  • the (hetero)aralkyl group having 7 to 40 carbon atoms include a phenylmethyl group, a phenylethyl group, a phenylpropyl group, a phenylhexyl group, a phenyloctyl group, a phenyldecyl group, and a dibenzofurylpropyl group. From the viewpoint of element stability, the phenylpropyl group and the phenylhexyl group are preferred.
  • alkoxy group having 1 to 20 carbon atoms examples include a methoxy group, an ethoxy group, a butyloxy group, and a hexyloxy group, and from the viewpoint of the stability of the element, a methoxy group and an ethoxy group are preferable.
  • Examples of (hetero)aryloxy groups having 3 to 20 carbon atoms include phenoxy groups, naphthyloxy groups, and carbazolyloxy groups, with the phenoxy group being preferred from the viewpoint of element stability.
  • alkylsilyl group having 1 to 20 carbon atoms examples include a trimethylsilyl group, a triethylsilyl group, and a tertiary butyldimethylsilyl group, and from the viewpoint of element stability, the trimethylsilyl group is preferred.
  • arylsilyl group having 6 to 20 carbon atoms examples include a dimethylphenylsilyl group and a triphenylsilyl group.
  • arylamino group having 6 to 20 carbon atoms include a diphenylamino group, a biphenylphenylamino group, and a naphthylphenyl group, and from the viewpoint of element stability, the diphenylamino group is preferred.
  • the (hetero)aryl group having 3 to 30 carbon atoms include a phenyl group, a naphthyl group, an anthranyl group, a biphenyl group, a terphenyl group, a carbazolyl group, a thienyl group, a benzofuryl group, a benzothienyl group, a dibenzofuryl group, a dibenzothienyl group, and a phenylthienyl group.
  • the phenyl group, the naphthyl group, the biphenyl group, the terphenyl group, the carbazolyl group, and the dibenzofuryl group are preferred, and the phenyl group, the biphenyl group, and the terphenyl group are more preferred.
  • Each R 1 is independently a hydrogen atom, a (hetero)aryl group having 3 to 20 carbon atoms which may have a substituent, or a bond to Ar 2 , and at least one of R 1's is a bond to Ar 2 .
  • R 1 other than the bond to Ar 2 is preferably a hydrogen atom or an aryl group having 3 to 20 carbon atoms which may have a substituent.
  • the (hetero)aryl group having 3 to 20 carbon atoms which may have a substituent include a phenyl group, a naphthyl group, an anthranyl group, a biphenyl group, a terphenyl group, a carbazolyl group, a thienyl group, a benzofuryl group, a benzothienyl group, a dibenzofuryl group, a dibenzothienyl group, a phenylthienyl group, etc., and from the viewpoint of extending the life of the element, the phenyl group, the naphthyl group, the biphenyl group, the terphenyl group, the carbazolyl group, and the dibenzofuryl group are preferred, and the phenyl group, the biphenyl group, and the terphenyl group are more preferred.
  • the substituent that R 1 may have is preferably a substituent selected from the substituent group Z described below.
  • ⁇ Preferable range of formula (2b) ⁇ Ar3 is a (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent.
  • Specific examples of the (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent include a phenyl group, a naphthyl group, an anthranyl group, a biphenyl group, a terphenyl group, a carbazolyl group, a thienyl group, a benzofuryl group, a benzothienyl group, a dibenzofuryl group, a dibenzothienyl group, a phenylthienyl group, etc., and from the viewpoint of extending the life of the element, the phenyl group, the naphthyl group, the biphenyl group, the terphenyl group, the carbazolyl group, and the dibenzofuryl group are preferred, and the phenyl group, the
  • the substituent that Ar3 may have is preferably a substituent selected from the substituent group Z described below.
  • Each R2 is independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a (hetero)aralkyl group having 7 to 40 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a (hetero)aryloxy group having 3 to 20 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an arylamino group having 6 to 20 carbon atoms, or a (hetero)aryl group having 3 to 30 carbon atoms.
  • These groups, except for the hydrogen atom may have a substituent.
  • the substituent that R2 may have is preferably a substituent selected from the substituent group Z described below.
  • Examples of the alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a propyl group, a hexyl group, an octyl group, a decyl group, etc. From the viewpoint of element stability, a methyl group, an ethyl group, and a hexyl group are preferable, and a methyl group is more preferable.
  • the (hetero)aralkyl group having 7 to 40 carbon atoms include a phenylmethyl group, a phenylethyl group, a phenylpropyl group, a phenylhexyl group, a phenyloctyl group, a phenyldecyl group, and a dibenzofurylpropyl group. From the viewpoint of element stability, the phenylpropyl group and the phenylhexyl group are preferred.
  • Examples of the alkoxy group having 1 to 20 carbon atoms include a methoxy group, an ethoxy group, a butyloxy group, and a hexyloxy group, and from the viewpoint of the stability of the element, a methoxy group and an ethoxy group are preferable.
  • Examples of the (hetero)aryloxy group having 3 to 20 carbon atoms include a phenoxy group, a naphthyloxy group, and a carbazolyloxy group, and from the viewpoint of the stability of the element, the phenoxy group is preferred.
  • alkylsilyl group having 1 to 20 carbon atoms examples include a trimethylsilyl group, a triethylsilyl group, and a tertiary butyldimethylsilyl group, and from the viewpoint of element stability, the trimethylsilyl group is preferred.
  • arylsilyl group having 6 to 20 carbon atoms examples include a dimethylphenylsilyl group and a triphenylsilyl group.
  • arylamino group having 1 to 20 carbon atoms include a diphenylamino group, a biphenylphenylamino group, and a naphthylphenyl group, and from the viewpoint of element stability, the diphenylamino group is preferred.
  • the (hetero)aryl group having 3 to 30 carbon atoms include a phenyl group, a naphthyl group, an anthranyl group, a biphenyl group, a terphenyl group, a carbazolyl group, a thienyl group, a benzofuryl group, a benzothienyl group, a dibenzofuryl group, a dibenzothienyl group, and a phenylthienyl group.
  • the phenyl group, the naphthyl group, the biphenyl group, the terphenyl group, the carbazolyl group, and the dibenzofuryl group are preferred, and the phenyl group, the biphenyl group, and the terphenyl group are more preferred.
  • R 1 , R 2 , Ar 2 and Ar 3 are preferably substituents selected from the substituent group Z described below.
  • the compound represented by the above formula (2) is preferably a charge transport compound, that is, a charge transport host material.
  • the composition for forming a light emitting layer according to the embodiment of the present invention may contain only one type of compound represented by the formula (2), or may contain two or more types of compounds.
  • Ar 4 is a structure represented by the above formula (2a).
  • Ar 5 is a group selected from the same groups as Ar 2 in the above formula (2)
  • Ar 6 is a group selected from the same groups as Ar 3 in the above formula (2b)
  • R 3 is each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a (hetero)aralkyl group having 7 to 40 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a (hetero)aryloxy group having 3 to 20 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an arylamino group having 6 to 20 carbon atoms, or a (hetero)aryl group having 3 to 30 carbon atoms.
  • Ar 5 is preferably a (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent, and more preferably an aryl group having 6 to 60 carbon atoms.
  • Ar 5 include divalent groups derived from a benzene ring, a naphthalene ring, a dibenzofuran ring, a thiophene ring, a dibenzothiophene ring, and a carbazole ring, and also include divalent groups formed by bonding these together, such as a divalent group derived from phenylthiophene formed by bonding a benzene ring and a thiophene ring.
  • Ar 6 is a (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent.
  • Specific examples of the (hetero)aryl group having 6 to 60 carbon atoms which may have a substituent include a phenyl group, a naphthyl group, an anthranyl group, a biphenyl group, a terphenyl group, a carbazolyl group, a thienyl group, a benzofuryl group, a benzothienyl group, a dibenzofuryl group, a dibenzothienyl group, a phenylthienyl group, etc., and from the viewpoint of extending the life of the element, the phenyl group, the naphthyl group, the biphenyl group, the terphenyl group, the carbazolyl group, and the dibenzofuryl group are preferred, and the phenyl group, the biphenyl group, and the terpheny
  • R 3 is each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a (hetero)aralkyl group having 7 to 40 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a (hetero)aryloxy group having 3 to 20 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an arylamino group having 6 to 20 carbon atoms, or a (hetero)aryl group having 3 to 30 carbon atoms.
  • a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a (hetero)aralkyl group having 7 to 40 carbon atoms, a (hetero)aryloxy group having 3 to 20 carbon atoms, an arylamino group having 6 to 20 carbon atoms, or a (hetero)aryl group having 3 to 30 carbon atoms is preferable, and a hydrogen atom or an aryl group having 3 to 30 carbon atoms is more preferable.
  • Examples of the alkyl group having 1 to 20 carbon atoms include a methyl group, an ethyl group, a propyl group, a hexyl group, an octyl group, a decyl group, etc. From the viewpoint of element stability, a methyl group, an ethyl group, and a hexyl group are preferable, and a methyl group is more preferable.
  • the (hetero)aralkyl group having 7 to 40 carbon atoms include a phenylmethyl group, a phenylethyl group, a phenylpropyl group, a phenylhexyl group, a phenyloctyl group, a phenyldecyl group, and a dibenzofurylpropyl group. From the viewpoint of element stability, the phenylpropyl group and the phenylhexyl group are preferred.
  • Examples of the alkoxy group having 1 to 20 carbon atoms include a methoxy group, an ethoxy group, a butyloxy group, and a hexyloxy group, and from the viewpoint of the stability of the element, a methoxy group and an ethoxy group are preferable.
  • Examples of the (hetero)aryloxy group having 3 to 20 carbon atoms include a phenoxy group, a naphthyloxy group, and a carbazolyloxy group, and from the viewpoint of the stability of the element, the phenoxy group is preferred.
  • alkylsilyl group having 1 to 20 carbon atoms examples include a trimethylsilyl group, a triethylsilyl group, and a tertiary butyldimethylsilyl group, and from the viewpoint of element stability, the trimethylsilyl group is preferred.
  • arylsilyl group having 6 to 20 carbon atoms examples include a dimethylphenylsilyl group and a triphenylsilyl group.
  • arylamino group having 1 to 20 carbon atoms include a diphenylamino group, a biphenylphenylamino group, and a naphthylphenyl group, and from the viewpoint of element stability, the diphenylamino group is preferred.
  • the (hetero)aryl group having 3 to 30 carbon atoms include a phenyl group, a naphthyl group, an anthranyl group, a biphenyl group, a terphenyl group, a carbazolyl group, a thienyl group, a benzofuryl group, a benzothienyl group, a dibenzofuryl group, a dibenzothienyl group, and a phenylthienyl group.
  • the phenyl group, the naphthyl group, the biphenyl group, the terphenyl group, the carbazolyl group, and the dibenzofuryl group are preferred, and the phenyl group, the biphenyl group, and the terphenyl group are more preferred.
  • R 3 , Ar 5 and Ar 6 are preferably substituents selected from the substituent group Z described below.
  • the compound represented by the above formula (2-1) is preferably a charge transport compound, that is, a charge transport host material.
  • the composition for forming a light emitting layer according to the embodiment of the present invention may contain only one type of compound represented by the formula (2-1), or may contain two or more types of compounds.
  • the molecular weight of the compound (2-1) is usually 5000 or less, preferably 3000 or less, more preferably 2500 or less, particularly preferably 2000 or less, and most preferably 1800 or less.
  • the lower limit of the molecular weight of the compound (2-1) is preferably 350 or more, more preferably 400 or more, and particularly preferably 500 or more.
  • Each W independently represents CH or N, and at least one W is N;
  • Xa 1 , Ya 1 , and Za 1 each independently represent a divalent aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, or a divalent aromatic heterocyclic group having 3 to 30 carbon atoms which may have a substituent, and when there are a plurality of Xa 1 , Ya 1 , and Za 1 , they may be the same or different,
  • Xa 2 , Ya 2 and Za 2 each independently represent a hydrogen atom, a monovalent aromatic hydrocarbon group having 6 to 30 carbon atoms which may have a substituent, or a monovalent aromatic heterocyclic group having 3 to 30 carbon atoms which may have a substituent;
  • 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, When g11 is 2 or more, the multiple Xa1 '
  • the compound represented by the above formula (1) is preferably a charge transport compound, i.e., a charge transport host material.
  • W represents CH or N, and at least one of them is N. From the viewpoints of electron transport properties and electron durability, it is preferable that at least two of them are N, and it is more preferable that all of them are N.
  • the aromatic hydrocarbon ring of the aromatic hydrocarbon group having 6 to 30 carbon atoms is preferably a 6-membered monocyclic ring or 2 to 5 condensed rings.
  • 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, and an indenofluorene ring.
  • a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, or a fluorene ring is preferred, a benzene ring, a naphthalene ring, a phenanthrene ring, or a fluorene ring is more preferred, and a benzene ring, a naphthalene ring, or a fluorene ring is even more preferred.
  • -Xa 1 -Xa 2 which is a terminal partial structure when g11 is 2 or more
  • -Ya 1 -Ya 2 which is a terminal partial structure when h11 is 2 or more
  • -Za 1 -Za 2 which is a terminal partial structure when j11 is 2 or more
  • -Xa 1 -Xa 2 which is a terminal partial structure when g11 is 2 or more
  • -Ya 1 -Ya 2 which is a terminal partial structure when h11 is 2 or more
  • -Za 1 -Za 2 which is a terminal partial structure when j11 is 2 or more
  • At least one of -Xa 1 -Xa 2 which is a terminal partial structure when g11 is 2 or more, -Ya 1 -Ya 2 , which is a terminal partial structure when h11 is 2 or more, and -Za 1 -Za 2 , which is a terminal partial structure when j11 is 2 or more, is preferably a spirofluorene structure.
  • the aromatic heterocycle of the aromatic heterocyclic group having 3 to 30 carbon atoms is preferably a 5- or 6-membered monocycle, or 2- to 5-condensed rings.
  • a furan ring a benzofuran ring, a dibenzofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a pyrrole ring, a pyrazole ring, an imidazole ring, an oxadiazole ring, an indole ring, a carbazole ring, an indolocarbazole ring, an indenocarbazole ring, a pyrroloimidazole ring, a pyrrolopyrazole ring, a pyrrolopyrrole ring, a thienopyrrole ring, a thienothiophene ring, a furopyrrole ring, a furofuran ring, a thienofuran ring, a benzisoxazole ring, a benzisothiazole ring, a benzisothi
  • a thiophene ring, a pyrrole ring, an imidazole ring, 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, a phenanthroline ring, or an indenocarbazole ring is preferred, a pyridine ring, a pyrimidine ring, a triazine ring, a quinoline ring, a quinazoline ring, a carbazole ring, an indolocarbazole ring, an indenocarbazole ring, a dibenzofuran ring, or a dibenzothiophene ring is more preferred, and a carbazole ring, an indolocarbazole ring, an in
  • particularly preferred aromatic hydrocarbon rings are a benzene ring, a naphthalene ring, or a phenanthrene ring
  • particularly preferred aromatic heterocycles are a carbazole ring, an indolocarbazole 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 transport properties 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 formula (1) preferably has a total of 8 to 18 rings, including the ring having three central Ws, from the viewpoints of charge transportability, durability, and solubility in organic solvents.
  • At least one group selected from ( Xa1 ) g11 , ( Ya1 ) h11, and ( Za1 ) j11 preferably each independently has a partial structure selected from a partial structure represented by the following formula (11), a partial structure represented by the following formula (12), and a partial structure represented by the following formula (13), and it is more preferable that ( Xa1 ) g11 when g11 is 1 or more, ( Ya1 ) h11 when h11 is 1 or more, and ( Za1 ) j11 when j11 is 1 or more each independently have a partial structure selected from a partial structure represented by the following formula (11), a partial structure represented by the following formula (12), and a partial structure represented by the following formula (13).
  • * represents a bonding position with an adjacent structure, or a hydrogen atom when Xa 2 , Ya 2 , or Za 2 is a hydrogen atom. At least one of the two * represents a bonding position with an adjacent structure.
  • the definition of * is the same unless otherwise specified.
  • (Xa 1 ) g11 when g11 is 1 or more, (Ya 1 ) h11 when h11 is 1 or more, and (Za 1 ) j11 when j11 is 1 or more each independently have a partial structure represented by formula (11) or a partial structure represented by formula (12). More preferably, (Xa 1 ) g11 when g11 is 1 or more, (Ya 1 ) h11 when h11 is 1 or more, and (Za 1 ) j11 when j11 is 1 or more each independently have a partial structure represented by formula (11) and a partial structure represented by formula (12).
  • the partial structure represented by formula (12) is preferably the partial structure represented by formula (12-2) below.
  • the partial structure represented by formula (12) is even more preferably the partial structure represented by formula (12-3) below.
  • the partial structure having the partial structure represented by formula (11) and the partial structure represented by formula (12) is preferably a partial structure selected from the following formulas (14) to (17), which is a structure containing a plurality of structures selected from the partial structure represented by formula (11) and the partial structure represented by formula (12). That is, it is preferable that (Xa 1 ) g11 when g11 is 1 or more, (Ya 1 ) h11 when h11 is 1 or more, and (Za 1 ) j11 when j11 is 1 or more each independently have a partial structure selected from the above formulas (11) to (13) and the following formulas (14) to (17).
  • the structure containing a plurality of structures selected from the partial structure represented by formula (11) and the partial structure represented by formula (12) is, for example, a partial structure represented by formula (14) that can be regarded as having one partial structure represented by formula (11) and two partial structures represented by formula (12), as in the following formula (14a).
  • At least one of ( Xa1 ) g11 , ( Ya1 ) h11, and ( Za1 ) j11 has at least a partial structure represented by formula (14) or a partial structure represented by formula (15). More preferably, ( Xa1 ) g11 when g11 is 1 or more, ( Ya1 ) h11 when h11 is 1 or more, and ( Za1 ) j11 when j11 is 1 or more have a partial structure represented by formula (14) or a partial structure represented by formula (15).
  • the partial structure represented by formula (14) is preferably the partial structure represented by formula (14-2) below.
  • the partial structure represented by formula (14) is more preferably the partial structure represented by formula (14-3) below.
  • the partial structure represented by formula (15) is preferably the partial structure represented by formula (15-2) below.
  • the partial structure represented by formula (15) is more preferably the partial structure represented by formula (15-3) below.
  • the partial structure represented by formula (17) is preferably the partial structure represented by formula (17-2) below.
  • At least one of (Xa 1 ) g11 , (Ya 1 ) h11 , and (Za 1 ) j11 has a partial structure represented by the following formula (19) or a partial structure represented by the following formula (20) as a partial structure including a partial structure represented by formula (13).
  • * represents a bonding position with an adjacent structure, or a hydrogen atom when Xa 2 , Ya 2 , or Za 2 is a hydrogen atom. At least one of the two * represents a bonding position with an adjacent structure.
  • -(Xa 1 ) g11 -(Xa 2 ), -(Ya 1 ) h11 -(Ya 2 ), and -(Za 1 ) j11 -(Za 2 ) each independently have a partial structure represented by formula (11), a partial structure represented by formula (12-3), a partial structure represented by formula (14-3), or a partial structure represented by formula (15-3).
  • At least one of -(Xa 1 ) g11 -(Xa 2 ), -(Ya 1 ) h11 -(Ya 2 ), and -(Za 1 ) j11 -(Za 2 ) preferably has any one of the partial structures or terminal structures represented by the following formulae (250-1) to (250-10).
  • Ar 250 represents an aromatic hydrocarbon group having 6 to 20 carbon atoms.
  • R 32 represents a substituent. These structures may further have a substituent.
  • Ar 250 is preferably an aromatic hydrocarbon group having 6 to 20 carbon atoms, more preferably a phenyl group or a biphenyl group, and even more preferably a phenyl group.
  • R 32 is preferably an alkyl group having 1 to 20 carbon atoms, an aralkyl group having 7 to 40 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an alkylsilyl group having 1 to 20 carbon atoms, an arylsilyl group having 6 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms which may be substituted with an alkyl group having 1 to 8 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms which may be substituted with an alkyl group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 20 carbon atoms, an aralkyl group having 7 to 40 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an ary
  • R 31 is a substituent, 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 preferably an aromatic hydrocarbon group which may have a substituent. When there are a plurality of R 31 as a substituent, they may be different from each other.
  • the substituent which the aromatic hydrocarbon group having 6 to 30 carbon atoms may have, the substituent which the aromatic heterocyclic group having 3 to 30 carbon atoms may have, and the substituent R 31 may have can be selected from the substituent group Z described later.
  • the molecular weight of compound (1) is usually 5,000 or less, preferably 3,000 or less, more preferably 2,500 or less, particularly preferably 2,000 or less, and most preferably 1,800 or less.
  • the lower limit of the molecular weight of compound (1) is usually 350 or more, more preferably 400 or more, and particularly preferably 500 or more.
  • the compound represented by formula (1) is not particularly limited, but examples thereof include the following compounds.
  • the light-emitting layer and the composition for forming the light-emitting layer according to the embodiment of the present invention may contain only one type of compound represented by formula (1), or may contain two or more types.
  • Formula (1) is preferably represented by formula (1-1) or formula (1-2).
  • each R 11 independently represents a hydrogen atom or a substituent.
  • R 11 which is a substituent other than a hydrogen atom include groups selected from the substituent group Z described below.
  • the substituent group Z 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 is preferable. From the viewpoint of improving durability and charge transportability, an aromatic hydrocarbon group which may have a substituent is more preferable.
  • the plurality of R 11 may be the same or different from each other.
  • the substituent which the aromatic hydrocarbon group having 6 to 30 carbon atoms may have, the substituent which the aromatic heterocyclic group having 3 to 30 carbon atoms may have, and the substituent R 11 may have can be selected from the substituent group Z described later.
  • W 1 , W 2 and W 3 each independently represent -CH or a nitrogen atom, and at least one of W 1 , W 2 and W 3 is a nitrogen atom;
  • Xa 1 , Ya 1 , and Za 1 each independently represent a 1,3-phenylene group which may have a substituent or a 1,4-phenylene group which may have a substituent, and when a plurality of Xa 1 , Ya 1 , and Za 1 are present, they may be the same or different, At least one of Za 1 is a 1,3-phenylene group;
  • Xa2 and Ya2 each independently represent a phenyl group which may have a substituent;
  • Za2 represents an N-carbazolyl group which may have a substituent.
  • f11 is 1 or 2;
  • g11 is an integer from 1 to 5, h11 is an integer from 2 to 5, j11 is an integer from 1 to 6,
  • Each R 11 independently represents a hydrogen atom or a substituent.
  • W 1 , W 2 , and W 3 each independently represent -CH or a nitrogen atom, and at least one of W 1 , W 2 , and W 3 is a nitrogen atom. From the viewpoint of electron transportability and electron durability, it is preferable that at least W 1 is a nitrogen atom, it is preferable that at least W 1 and W 2 are nitrogen atoms, and it is more preferable that all of W 1 , W 2 , and W 3 are nitrogen atoms.
  • the group bonded to the para position has two or three benzene rings linked at the para position to expand conjugation, and W1 is a nitrogen atom, a pyrimidine structure in which in addition to W1 , one of W2 and W3 is a nitrogen atom is more preferable, and a triazine structure in which W1 , W2 and W3 are all nitrogen atoms is most preferable.
  • ⁇ -(Xa 1 ) g11 -Xa 2 > In formula (1-1), it is preferable that at least one of Xa 1 is a 1,3-phenylene group. In particular, it is more preferable that -(Xa 1 ) g11 -Xa 2 is selected from the structure group of formula (Xa-1) below.
  • the hydrogen atoms may be substituted with a substituent selected from the substituent group Z.
  • the hydrogen atoms are not substituted.
  • the hydrogen atoms may be substituted with a substituent selected from the substituent group Z.
  • the hydrogen atoms are not substituted.
  • ⁇ -(Za 1 ) j11 -Za 2 > In formula (1-1), it is preferable that at least one of Za 1 is a 1,3-phenylene group. In particular, it is more preferable that -(Za 1 ) j11 -Za 2 is selected from the structure group of formula (Za-1) below.
  • the hydrogen atoms may be substituted with a substituent selected from the substituent group Z.
  • the hydrogen atoms are not substituted.
  • the molecular weight of the compound (1-1) is usually 5,000 or less, preferably 3,000 or less, more preferably 2,500 or less, particularly preferably 2,000 or less, and most preferably 1,800 or less.
  • the lower limit of the molecular weight of the compound (1-1) is preferably 350 or more, more preferably 400 or more, and particularly preferably 500 or more.
  • the group bonded to the para position of W 3 is a 1,3-phenylene group and is therefore not conjugated, and therefore compound (1-1) has a wide energy gap and is considered preferable when used as a matrix material for a light-emitting layer because it is unlikely to quench the light-emitting material.
  • At least one of Za 1 in compound (1-1) is a 1,3-phenylene group and is not conjugated with Za 2 which is a carbazolyl group. Therefore, compound (1-1) has a wide energy gap and is considered preferable because it is unlikely to quench the light-emitting material when used as a matrix material for the light-emitting layer.
  • -(Xa 1 ) g11 -Xa 2 , -(Ya 1 ) h11 -Ya 2 and -(Za 1 ) j11 -Za 2 are the preferred structures, they have a wide energy gap and are unlikely to quench the light-emitting material when used as a matrix material for the light-emitting layer.
  • the compound (1-2) is a compound represented by the following formula (1-2).
  • W 1 , W 2 and W 3 each independently represent -CH or a nitrogen atom, and at least one of W 1 , W 2 and W 3 is a nitrogen atom;
  • Xa 1 , Ya 1 , and Za 1 each independently represent a 1,3-phenylene group which may have a substituent or a 1,4-phenylene group which may have a substituent, and when a plurality of Xa 1 , Ya 1 , and Za 1 are present, they may be the same or different, At least one of Ya1 and Za1 is a 1,3-phenylene group which may have a substituent;
  • Xa2 represents a phenyl group which may have a substituent;
  • Ya2 and Za2 each independently represent an N-carbazolyl group which may have a substituent;
  • f11 is 1 or 2;
  • g11 is an integer from 1 to 5,
  • h11 is an integer from 2 to 5,
  • j11 is an integer from 2 to 5,
  • Each R 11 independently
  • W 1 , W 2 , and W 3 each independently represent -CH or a nitrogen atom, and at least one of W 1 , W 2 , and W 3 is a nitrogen atom. From the viewpoint of electron transportability and electron durability, it is preferable that at least W 1 is a nitrogen atom, it is preferable that at least W 1 and W 2 are nitrogen atoms, and it is more preferable that all of W 1 , W 2 , and W 3 are nitrogen atoms.
  • the group bonded to the para position has two or three benzene rings linked at the para position to expand conjugation, and W1 is a nitrogen atom, a pyrimidine structure in which in addition to W1 , one of W2 and W3 is a nitrogen atom is more preferable, and a triazine structure in which W1 , W2 and W3 are all nitrogen atoms is most preferable.
  • ⁇ -(Xa 1 ) g11 -Xa 2 >
  • Xa 1 is a 1,3-phenylene group.
  • -(Xa 1 ) g11 -Xa 2 is selected from the structure group of formula (Xa-2) below.
  • the hydrogen atoms may be substituted with a substituent selected from the substituent group Z.
  • the hydrogen atoms are not substituted.
  • Ya 1 is a 1,3-phenylene group.
  • -(Ya 1 ) h11 -Ya 2 is selected from the structure group of formula (Ya-2) below.
  • all hydrogen atoms on the benzene ring may be substituted with a substituent selected from the substituent group Z.
  • the hydrogen atoms are not substituted.
  • ⁇ -(Za 1 ) j11 -Za 2 >
  • Za 1 is a 1,3-phenylene group.
  • -(Za 1 ) j11 -Za 2 is selected from the structure group of formula (Za-2) below.
  • all hydrogen atoms on the benzene ring may be substituted with a substituent selected from the substituent group Z.
  • the hydrogen atoms are not substituted.
  • h11 is 2 or more, and is preferably 2 or 4.
  • j11 is 2 or more, and is preferably 2 or 4.
  • At least one of Xa 1 is preferably a 1,3-phenylene group, and more preferably all of Xa 1 are 1,3-phenylene groups.
  • Xa 1 is a 1,3-phenylene group
  • conjugation is broken and solubility is increased.
  • at least one Ya 1 is preferably a 1,3-phenylene group, and it is more preferable that all Ya 1 are 1,3-phenylene groups.
  • Ya 1 is a 1,3-phenylene group, conjugation is broken and solubility is increased.
  • it is preferable that at least one of Za 1 is a 1,3-phenylene group, and it is more preferable that all of Za 1 are 1,3-phenylene groups.
  • Za 1 is a 1,3-phenylene group
  • conjugation is broken and solubility is increased.
  • at least one Ya 1 is a 1,3-phenylene group and at least one Za 1 is a 1,3-phenylene group.
  • the molecular weight of the compound (1-2) is usually 5,000 or less, preferably 3,000 or less, more preferably 2,500 or less, particularly preferably 2,000 or less, and most preferably 1,800 or less.
  • the lower limit of the molecular weight of the compound (1-2) is preferably 350 or more, more preferably 400 or more, and particularly preferably 500 or more.
  • the group bonded to the para position of W1 is a group in which two or three benzene rings are linked at the para position, so that conjugation is widespread, LUMO is distributed therein, and it is considered that the compound has excellent electron transport properties.
  • the number of benzene rings linked in conjugation to the para position of W1 is three or less, the conjugation is not too long and the compound has a wide energy gap, so that when the compound is used as a matrix material for the light-emitting layer, it is considered that the compound is preferable because it is unlikely to quench the light-emitting material.
  • the group bonded to the para position of W 3 is a 1,3-phenylene group and is therefore not conjugated, and therefore compound (1-2) has a wide energy gap and is considered preferable when used as a matrix material for a light-emitting layer because it is unlikely to quench the light-emitting material.
  • At least one of Ya 1 and Za 1 in compound (1-2) is a 1,3-phenylene group and is not conjugated with Ya 2 or Za 2 which is an N-carbazolyl group. Therefore, compound (1-2) has a wide energy gap and is considered to be preferable because it is unlikely to quench the light-emitting material when used as a matrix material for the light-emitting layer.
  • -(Xa 1 ) g11 -Xa 2 , -(Ya 1 ) h11 -Ya 2 and -(Za 1 ) j11 -Za 2 are the preferred structures, they have a wide energy gap and are unlikely to quench the light-emitting material when used as a matrix material for the light-emitting layer.
  • compound (1-2) has three or more phenylene groups between the nitrogen-containing 6-membered ring containing W 1 , W 2 and W 3 and the carbazolyl group, contains a moderate number of 1,3-phenylene groups, and does not contain a 1,4-phenylene linking structure longer than a terphenylene group, and therefore has excellent solubility.
  • composition for forming a light emitting layer according to an embodiment of the present invention may further contain a compound represented by the following formula (4).
  • Compound (4) is a compound represented by the following formula (4).
  • Ar 61 to Ar 65 each independently represent a hydrogen atom or a monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent
  • L 1 to L 5 each independently represent a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent, and when a plurality of L 1 to L 5 are present, they may be the same or different
  • Each R 60 independently represents a substituent.
  • n represents an integer from 0 to 10
  • a1 to a3 each independently represents an integer of 0 to 3
  • at least one of Ar 61 , Ar 62 , Ar 63 , Ar 64 , and at least one Ar 65 when n is 1 or more, is not a hydrogen atom.
  • Ar 61 , Ar 62 , Ar 65 each independently represent a hydrogen atom or a monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent.
  • Ar 61 , Ar 62 and Ar 65 are preferably a hydrogen atom, a monovalent group of a benzene ring, a monovalent group of a naphthalene ring, or a structure represented by formula (261) or formula (262), more preferably a hydrogen atom, a monovalent group of a benzene ring, or a structure represented by formula (261) or formula (262), still more preferably a hydrogen atom, a monovalent group of a benzene ring, or a structure represented by formula (262), and particularly preferably a structure represented by formula (262).
  • Ar 61 , Ar 62 , and at least one Ar 65 are represented by the following formula (261) or the following formula (262), and it is more preferable that one or more and three or less of Ar 61 , Ar 62 , and at least one Ar 65 are represented by the following formula (262).
  • one of Ar 61 , Ar 62 and at least one Ar 65 is represented by the following formula (262).
  • two or more of Ar 61 , Ar 62 and at least one Ar 65 are represented by the following formula (262), and it is more preferable that three of them are represented by the following formula (262).
  • R 101 to R 126 each independently represent a hydrogen atom or a substituent.
  • m1 is preferably 0 or 1, more preferably 0.
  • m2 is preferably 0 or 1, more preferably 0.
  • m5 is preferably 0 or 1, more preferably 0.
  • Ar 63 and Ar 64 each independently represent a hydrogen atom or a monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent.
  • the monovalent aromatic hydrocarbon group having 6 to 60 carbon atoms include monovalent groups of a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a tetraphenylene ring, a chrysene ring, a pyrene ring, a benzoanthracene ring, a perylene ring, a biphenyl ring, or a terphenyl ring.
  • Ar 63 and Ar 64 in formula (4) are each independently preferably a hydrogen atom, a monovalent group of a benzene ring, or a monovalent group of a naphthalene ring, more preferably a hydrogen atom or a monovalent group of a benzene ring.
  • L 1 to L 5 each independently represent a divalent aromatic hydrocarbon group having 6 to 60 carbon atoms which may have a substituent.
  • divalent aromatic hydrocarbon groups having 6 to 60 carbon atoms include divalent groups of a benzene ring, a naphthalene ring, an anthracene ring, a tetraphenylene ring, a phenanthrene ring, a chrysene ring, a pyrene ring, a benzoanthracene ring, or a perylene ring.
  • Each of L 1 to L 5 independently represents preferably a phenylene group or a divalent group in which two or more, for example, 2 to 5, phenylene groups are linked by direct bonds, which may have a substituent, and more preferably a 1,3-phenylene group which may have a substituent from the viewpoint of solubility.
  • Each R 60 in formula (4) independently represents a substituent.
  • the substituent one selected from the above-mentioned substituent group Z can be used. Among them, an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, an alkoxycarbonyl group, an acyl group, a halogen atom, a haloalkyl group, an alkylthio group, an arylthio group, a silyl group, a siloxy group, an aralkyl group, or an aromatic hydrocarbon group is preferred.
  • an alkyl group, an alkenyl group, an alkoxy group, an aryloxy group, an alkoxycarbonyl group, an acyl group, a halogen atom, a haloalkyl group, a silyl group, a siloxy group, an aralkyl group, or an aromatic hydrocarbon group is preferred, an alkyl group, an alkoxy group, an aralkyl group, or an aromatic hydrocarbon group is more preferred, an alkyl group having 10 or less carbon atoms, an aralkyl group having 30 or less carbon atoms, or an aromatic hydrocarbon group having 30 or less carbon atoms is more preferred, and a benzene ring or a group in which 2 to 5 benzene rings are linked is particularly preferred.
  • m1, m2, and m5 each independently represent an integer of 0 to 5.
  • m3 and m4 each independently represent an integer of 0 to 5.
  • m1, m2 and m5 are preferably 4 or less, more preferably 3 or less, even more preferably 2 or less, particularly preferably 1 or less, and most preferably 0, from the viewpoint of the solubility and durability of the compound.
  • m1 when Ar 61 is formula (261) or formula (262), m2 when Ar 62 is formula (261) or formula (262), and m5 when Ar 65 is formula (261) or formula (262) are 0.
  • m3 and m4 are preferably 1 or more, preferably 4 or less, more preferably 3 or less, and particularly preferably 2 or less, from the viewpoint of the solubility and durability of the compound.
  • m1 in formula (4) is 2 or more
  • multiple L1s may be the same or different.
  • m2 in formula (4) is 2 or more
  • multiple L2s may be the same or different.
  • m3 in formula (4) is 2 or more
  • multiple L3s may be the same or different.
  • m4 in formula (4) is 2 or more
  • multiple L4s may be the same or different.
  • m5 in formula (4) is 2 or more, multiple L5s may be the same or different.
  • At least one group among (L 1 ) m1 , (L 2 ) m2 , (L 3 ) m3 , (L 4 ) m4 , and at least one (L 5 ) m5 in formula ( 4 ) preferably has a partial structure selected from a partial structure represented by the following formula (11), a partial structure represented by the following formula (12), and a partial structure represented by the following formula (13).
  • (L 1 ) m1 when m1 is 1 or more, (L 2 ) m2 when m2 is 1 or more, (L 5 ) m5 when n is 1 or more and m5 is 1 or more, (L 3 ) m3 when m3 is 1 or more, and (L 4 ) m4 when m4 is 1 or more have a partial structure selected from a partial structure represented by the following formula (11), a partial structure represented by the following formula (12), and a partial structure represented by the following formula (13).
  • * represents a bonding position with an adjacent structure or a hydrogen atom when Ar 61 , Ar 62 , Ar 63 , Ar 64 or Ar 65 is a hydrogen atom, and at least one of the two * represents a bonding position with an adjacent structure.
  • the definition of * is the same unless otherwise specified.
  • At least one of (L 1 ) m1 , (L 2 ) m2 , (L 3 ) m3 , (L 4 ) m4 , and at least one of (L 5 ) m5 in formula (4) has a partial structure represented by formula (11) or a partial structure represented by formula (12).
  • (L 1 ) m1 when m1 is 1 or more, (L 2 ) m2 when m2 is 1 or more, (L 3 ) m3 when m3 is 1 or more, (L 4 ) m4 when m4 is 1 or more, and (L 5 ) m5 when n is 1 or more and m5 is 1 or more each have a partial structure represented by formula (11) or a partial structure represented by formula (12).
  • (L 1 ) m1 when m1 is 1 or more, (L 2 ) m2 when m2 is 1 or more, (L 3 ) m3 when m3 is 1 or more, (L 4 ) m4 when m4 is 1 or more, and (L 5 ) m5 when n is 1 or more and m5 is 1 or more each have a partial structure represented by formula (11) and a partial structure represented by formula (12).
  • formula (12) is preferably the following formula (12-2).
  • the partial structure that is preferably possessed by at least one of (L 1 ) m1 , (L 2 ) m2 , (L 3 ) m3 , (L 4 ) m4 , and (L 5 ) m5 in formula (4) is a partial structure having a partial structure represented by formula (11) and a partial structure represented by formula (12).
  • the partial structure having the partial structure represented by formula (11) and the partial structure represented by formula (12) is preferably a partial structure selected from the following formulas (14) to (17), which is a structure containing a plurality of structures selected from the partial structure represented by formula (11) and the partial structure represented by formula (12).
  • (L 1 ) m1 when m1 is 1 or more, (L 2 ) m2 when m2 is 1 or more, (L 3 ) m3 when m3 is 1 or more, (L 4 ) m4 when m4 is 1 or more, and (L 5 ) m5 when n is 1 or more and m5 is 1 or more each independently have a partial structure selected from the above formulas (11) to (13) and the following formulas (14) to (17).
  • a structure containing a plurality of structures selected from the partial structure represented by formula (11) and the partial structure represented by formula (12) is, for example, a partial structure that can be regarded as having one partial structure represented by formula (11) and two partial structures represented by formula (12), as in formula (14a) below.
  • At least one of ( L1 ) m1 , ( L2 ) m2 , ( L3 ) m3 , ( L4 ) m4 , and at least one of ( L5 ) m5 in formula (4) has a partial structure represented by formula (14) or a partial structure represented by formula (15).
  • ( L1 )m1 when m1 is 1 or more, (L2) m2 when m2 is 1 or more, ( L3 ) m3 when m3 is 1 or more, ( L4 ) m4 when m4 is 1 or more, and ( L5 ) m5 when n is 1 or more and m5 is 1 or more have a partial structure represented by formula (14) or a partial structure represented by formula (15).
  • formula (14) is preferably the following formula (14-2).
  • formula (14) is more preferably the following formula (14-3).
  • formula (15) is preferably the following formula (15-2).
  • formula (15) is more preferably the following formula (15-3).
  • formula (17) is preferably the following formula (17-2).
  • At least one of (L 1 ) m1 , (L 2 ) m2 , (L 3 ) m3 , (L 4 ) m4 , and at least one of (L 5 ) m5 in formula (4) has a partial structure represented by the following formula (19) or a partial structure represented by the following formula (20) as a partial structure including a partial structure represented by formula (13).
  • L 1 to L 5 have a partial structure represented by formula (11), a partial structure represented by formula (12-3), a partial structure represented by formula (14-3), or a partial structure represented by formula (15-3).
  • n represents an integer of 0 to 10.
  • n is preferably 1 or more, more preferably 2 or more, and is preferably 6 or less, further preferably 5 or less, particularly preferably 4 or less, from the viewpoint of the solubility and durability of the compound.
  • R 101 to R 126 each independently represent a hydrogen atom or a substituent.
  • substituent group Z one selected from the above-mentioned substituent group Z can be used.
  • an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, an alkoxycarbonyl group, an acyl group, a halogen atom, a haloalkyl group, an alkylthio group, an arylthio group, a silyl group, a siloxy group, an aralkyl group, or an aromatic hydrocarbon group is preferred.
  • an alkyl group, an alkenyl group, an alkoxy group, an aryloxy group, an alkoxycarbonyl group, an acyl group, a halogen atom, a haloalkyl group, a silyl group, a siloxy group, an aralkyl group, or an aromatic hydrocarbon group is preferred, a hydrogen atom or an aromatic hydrocarbon group is more preferred, and a hydrogen atom is particularly preferred.
  • an alkyl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, an alkoxycarbonyl group, an acyl group, a halogen atom, a haloalkyl group, an alkylthio group, an arylthio group, a silyl group, a siloxy group, an aralkyl group, or an aromatic hydrocarbon group is preferred
  • an alkyl group, an alkenyl group, an alkoxy group, an aryloxy group, an alkoxycarbonyl group, an acyl group, a halogen atom, a haloalkyl group, a silyl group, a siloxy group, an aralkyl group, or an aromatic hydrocarbon group is more preferred.
  • the molecular weight of the compound represented by formula (4) is preferably 3,000 or less, more preferably 2,500 or less, even more preferably 2,000 or less, particularly preferably 1,500 or less, and is usually 400 or more, preferably 500 or more, more preferably 600 or more.
  • the light-emitting layer and the composition for forming the light-emitting layer according to the embodiment of the present invention may contain only one type of compound represented by formula (4), or may contain two or more types.
  • the substituent group Z is an alkyl group, an aralkyl group, a heteroaralkyl group, an alkoxy group, an aryloxy group, a heteroaryloxy group, an alkylsilyl group, an arylsilyl group, an alkylcarbonyl group, an arylcarbonyl group, an alkylamino group, an arylamino group, an aryl group, or a heteroaryl group.
  • alkyl groups having 1 to 20 carbon atoms aralkyl groups having 7 to 40 carbon atoms, heteroaralkyl groups having 7 to 40 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, aryloxy groups having 6 to 20 carbon atoms, heteroaryloxy groups having 3 to 20 carbon atoms, alkylsilyl groups having 1 to 20 carbon atoms, arylsilyl groups having 6 to 20 carbon atoms, alkylcarbonyl groups having 2 to 20 carbon atoms, arylcarbonyl groups having 7 to 20 carbon atoms, alkylamino groups having 1 to 20 carbon atoms, arylamino groups having 6 to 20 carbon atoms, aryl groups having 6 to 30 carbon atoms, and heteroaryl groups having 3 to 30 carbon atoms, and more specifically, the substituents described in [Specific examples of substituents] below.
  • alkyl groups having 1 to 20 carbon atoms More preferred are alkyl groups having 1 to 20 carbon atoms, aralkyl groups having 7 to 40 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, aryloxy groups having 6 to 20 carbon atoms, and aryl groups having 6 to 30 carbon atoms.
  • the alkyl group having 1 to 20 carbon atoms may be any of linear, branched, and cyclic alkyl groups. More specifically, examples include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-octyl, isopropyl, isobutyl, isopentyl, t-butyl, and cyclohexyl groups. Among these, linear alkyl groups having 1 to 8 carbon atoms, such as methyl, ethyl, n-butyl, n-hexyl, and n-octyl groups, are preferred.
  • the (hetero)aralkyl group having 7 to 40 carbon atoms refers to a group in which some of the hydrogen atoms constituting a linear alkyl group, a branched alkyl group, or a cyclic alkyl group are substituted with an aryl group or a heteroaryl group. More specifically, examples include a 2-phenyl-1-ethyl group, a cumyl group, a 5-phenyl-1-pentyl group, a 6-phenyl-1-hexyl group, a 7-phenyl-1-heptyl group, and a tetrahydronaphthyl group. Among these, the 5-phenyl-1-pentyl group, the 6-phenyl-1-hexyl group, and the 7-phenyl-1-heptyl group are preferred.
  • alkoxy group having 1 to 20 carbon atoms include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a hexyloxy group, a cyclohexyloxy group, an octadecyloxy group, etc. Of these, a hexyloxy group is preferable.
  • Specific examples of the (hetero)aryloxy group having 3 to 20 carbon atoms include a phenoxy group, a 4-methylphenyloxy group, etc. Among these, the phenoxy group is preferable.
  • the alkylsilyl group having 1 to 20 carbon atoms may be one in which some of the alkyl groups are replaced with aryl groups, and specific examples thereof include a trimethylsilyl group, a triethylsilyl group, a triisopropylsilyl group, a dimethylphenylsilyl group, a t-butyldimethylsilyl group, a t-butyldiphenylsilyl group, etc.
  • a triisopropylsilyl group, a t-butyldimethylsilyl group, and a t-butyldiphenylsilyl group are preferred.
  • arylsilyl group having 6 to 20 carbon atoms include a diphenylpyridylsilyl group, a triphenylsilyl group, etc. Among these, a triphenylsilyl group is preferable.
  • alkylcarbonyl group having 2 to 20 carbon atoms include an acetyl group, a propionyl group, a pivaloyl group, a caproyl group, a decanoyl group, a cyclohexylcarbonyl group, etc. Among these, an acetyl group and a pivaloyl group are preferable.
  • Specific examples of the arylcarbonyl group having 7 to 20 carbon atoms include a benzoyl group, a naphthoyl group, an anthrayl group, etc. Of these, a benzoyl group is preferable.
  • alkylamino group having 1 to 20 carbon atoms include a methylamino group, a dimethylamino group, a diethylamino group, an ethylmethylamino group, a dihexylamino group, a dioctylamino group, a dicyclohexylamino group, etc.
  • a dimethylamino group and a dicyclohexylamino group are preferable.
  • arylamino group having 6 to 20 carbon atoms include a phenylamino group, a diphenylamino group, a di(4-tolyl)amino group, a di(2,6-dimethylphenyl)amino group, etc.
  • a diphenylamino group and a di(4-tolyl)amino group are preferred.
  • the (hetero)aryl group having 3 to 30 carbon atoms means an aromatic hydrocarbon group, an aromatic heterocyclic group, a linked aromatic hydrocarbon group in which a plurality of aromatic hydrocarbons are linked, a linked aromatic heterocyclic group in which a plurality of aromatic heterocyclic groups are linked, or a group in which at least one aromatic hydrocarbon and at least one aromatic heterocyclic ring are arbitrarily linked, all of which have one free atomic valence.
  • a benzene ring 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 chrysene ring, a triphenylene ring, a fluoranthene ring, a furan ring, a benzofuran ring, a dibenzofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a pyrrole ring, a pyrazole ring, an imidazole ring, an oxadiazole ring, an indole ring, a carbazole ring, a pyrrolyl ring, and a pyrrolyl ring, all of which have one
  • Examples of the ring include a midazole ring, a pyrrolopyrazole ring, a pyrrolopyrrole ring, a thienopyrrole ring, a thienothiophene ring, a furopyrrole ring, a furofuran ring, a thienofuran ring, a benzisoxazole ring, a benzisothiazole ring, a benzimidazole ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinoxaline ring, a perimidine ring, a quinazoline ring, a quinazolinone ring, and an azulene ring.
  • benzene rings, naphthalene rings, dibenzofuran rings, dibenzothiophene rings, carbazole rings, pyridine rings, pyrimidine rings, and triazine rings, each having one free valence are preferred, and among these, aryl groups having 6 to 18 carbon atoms, such as a benzene ring, naphthalene ring, or phenanthrene ring, which may have one free valence and be substituted with an alkyl group having 1 to 8 carbon atoms, or a pyridine ring, which may have one free valence and be substituted with an alkyl group having 1 to 4 carbon atoms, are more preferred, and aryl groups having 6 to 18 carbon atoms, such as a benzene ring, naphthalene ring, or phenanthrene ring, which may have one free valence and be substituted with an alkyl group
  • combinations of these substituents can be, for example, but are not limited to, a combination of an aryl group and an alkyl group, a combination of an aryl group and an aralkyl group, or a combination of an aryl group, an alkyl group and an aralkyl group.
  • a combination of an aryl group and an aralkyl group for example, a combination of a phenyl group, a biphenyl group or a terphenyl group and a 5-phenyl-1-pentyl group or a 6-phenyl-1-hexyl group can be used.
  • the luminescent material any known material that is usually used as a luminescent material for an organic electroluminescent element can be applied, and there is no particular limitation, as long as a substance that emits light at a desired emission wavelength and has good luminous efficiency is used.
  • the luminescent material may be a fluorescent compound or a phosphorescent compound, but from the viewpoint of internal quantum efficiency, a phosphorescent compound is preferable. More preferably, the red luminescent material and the green luminescent material are phosphorescent compounds, and the blue luminescent material is a fluorescent compound.
  • the phosphorescent compound is a compound that emits light from an excited triplet state.
  • Representative examples of the phosphorescent compound include metal complex compounds having Ir, Pt, Eu, etc., and the material structure preferably includes a metal complex.
  • examples of phosphorescent organometallic complexes that emit light via a triplet state include Werner-type complexes or organometallic complex compounds containing a metal selected from Groups 7 to 11 of the long-form periodic table (hereinafter, unless otherwise specified, the term "periodic table” refers to the long-form periodic table) as a central metal.
  • Examples of such phosphorescent compounds include the phosphorescent compounds described in WO 2014/024889, WO 2015/087961, WO 2016/194784, and JP 2014-074000 A.
  • the compound represented by the following formula (3) or the compound represented by the following formula (205) is used, and more preferably, the compound represented by the following formula (3).
  • M represents a metal.
  • specific examples of M include metal atoms selected from Groups 7 to 11 of the periodic table. Among these, preferred are ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum, and gold, and particularly preferred are trivalent metals such as iridium.
  • ring A1 represents an aromatic hydrocarbon ring structure which may have a substituent or an aromatic heterocyclic structure which may have a substituent.
  • Ring A2 represents an aromatic heterocyclic structure which may have a substituent.
  • R 201 and R 202 each independently represent a structure represented by formula (b), and "*" represents a bonding position with ring A1 or ring A2.
  • R 201 and R 202 may be the same or different, and when a plurality of R 201 and R 202 are present, they may be the same or different.
  • Ar 201 and Ar 203 each independently represent an aromatic hydrocarbon ring structure which may have a substituent, or an aromatic heterocyclic structure which may have a substituent.
  • Ar 202 represents an aromatic hydrocarbon ring structure which may have a substituent, an aromatic heterocyclic structure which may have a substituent, or an aliphatic hydrocarbon structure which may have a substituent. When a plurality of Ar 201 , Ar 202 and Ar 203 are present, they may be the same or different.
  • Substituents bonded to ring A1, substituents bonded to ring A2, or a substituent bonded to ring A1 and a substituent bonded to ring A2 may bond to each other to form a ring.
  • B 201 -L 200 -B 202 represents an anionic bidentate ligand.
  • B 201 and B 202 each independently represent a carbon atom, an oxygen atom, or a nitrogen atom, and these atoms may be atoms constituting a ring.
  • L 200 represents a single bond, or an atomic group constituting a bidentate ligand together with B 201 and B 202.
  • B 201 -L 200 -B 202 When a plurality of B 201 -L 200 -B 202 are present, they may be the same or different.
  • i1 and i2 each independently represent an integer of 0 to 12
  • i3 represents an integer of 0 or more, the upper limit of which is the number that can be substituted for Ar 202
  • i4 represents an integer of 0 or more, the upper limit of which is the number that can be substituted on Ar 201
  • k1 and k2 each independently represent an integer of 0 or more, the upper limit of which is the number of groups that can be substituted on ring A1 and ring A2
  • z represents an integer of 1 to 3.
  • substituent group S is preferably a group selected from the following substituent group S.
  • Substituent group S An alkyl group, preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 12 carbon atoms, still more preferably an alkyl group having 1 to 8 carbon atoms, and particularly preferably an alkyl group having 1 to 6 carbon atoms.
  • An alkoxy group preferably an alkoxy group having 1 to 20 carbon atoms, more preferably an alkoxy group having 1 to 12 carbon atoms, and even more preferably an alkoxy group having 1 to 6 carbon atoms.
  • An aryloxy group preferably an aryloxy group having 6 to 20 carbon atoms, more preferably an aryloxy group having 6 to 14 carbon atoms, even more preferably an aryloxy group having 6 to 12 carbon atoms, and particularly preferably an aryloxy group having 6 carbon atoms.
  • a heteroaryloxy group preferably a heteroaryloxy group having 3 to 20 carbon atoms, more preferably a heteroaryloxy group having 3 to 12 carbon atoms.
  • An alkylamino group preferably an alkylamino group having 1 to 20 carbon atoms, more preferably an alkylamino group having 1 to 12 carbon atoms.
  • An arylamino group preferably an arylamino group having 6 to 36 carbon atoms, more preferably an arylamino group having 6 to 24 carbon atoms.
  • An aralkyl group preferably an aralkyl group having 7 to 40 carbon atoms, more preferably an aralkyl group having 7 to 18 carbon atoms, and even more preferably an aralkyl group having 7 to 12 carbon atoms.
  • An alkenyl group preferably an alkenyl group having 2 to 20 carbon atoms, more preferably an alkenyl group having 2 to 12 carbon atoms, even more preferably an alkenyl group having 2 to 8 carbon atoms, and particularly preferably an alkenyl group having 2 to 6 carbon atoms.
  • An alkynyl group preferably an alkynyl group having 2 to 20 carbon atoms, more preferably an alkynyl group having 2 to 12 carbon atoms.
  • An aryl group preferably an aryl group having 6 to 30 carbon atoms, more preferably an aryl group having 6 to 24 carbon atoms, still more preferably an aryl group having 6 to 18 carbon atoms, and particularly preferably an aryl group having 6 to 14 carbon atoms.
  • a heteroaryl group preferably a heteroaryl group having 3 to 30 carbon atoms, more preferably a heteroaryl group having 3 to 24 carbon atoms, still more preferably a heteroaryl group having 3 to 18 carbon atoms, and particularly preferably a heteroaryl group having 3 to 14 carbon atoms.
  • An alkylsilyl group preferably an alkylsilyl group having an alkyl group with 1 to 20 carbon atoms, and more preferably an alkylsilyl group having an alkyl group with 1 to 12 carbon atoms.
  • An arylsilyl group preferably an arylsilyl group having an aryl group with 6 to 20 carbon atoms, and more preferably an arylsilyl group having an aryl group with 6 to 14 carbon atoms.
  • An alkylcarbonyl group preferably an alkylcarbonyl group having 2 to 20 carbon atoms.
  • An arylcarbonyl group preferably an arylcarbonyl group having 7 to 20 carbon atoms.
  • one or more hydrogen atoms may be replaced by fluorine atoms, or one or more hydrogen atoms may be replaced by deuterium atoms.
  • aryl is an aromatic hydrocarbon ring and heteroaryl is an aromatic heterocyclic ring.
  • substituent group S preferred are an alkyl group, an alkoxy group, an aryloxy group, an arylamino group, an aralkyl group, an alkenyl group, an aryl group, a heteroaryl group, an alkylsilyl group, an arylsilyl group, and groups in which one or more hydrogen atoms of these groups are replaced by fluorine atoms, a fluorine atom, a cyano group, or -SF5 .
  • it is an alkyl group, an arylamino group, an aralkyl group, an alkenyl group, an aryl group, a heteroaryl group, a group in which one or more hydrogen atoms of these groups are replaced with fluorine atoms, a fluorine atom, a cyano group, or -SF5 . More preferred are an alkyl group, an alkoxy group, an aryloxy group, an arylamino group, an aralkyl group, an alkenyl group, an aryl group, a heteroaryl group, an alkylsilyl group, and an arylsilyl group.
  • an alkyl group particularly preferred are an alkyl group, an arylamino group, an aralkyl group, an alkenyl group, an aryl group, and a heteroaryl group.
  • an alkyl group, an arylamino group, an aralkyl group, an aryl group and a heteroaryl group are particularly preferred.
  • substituents S may further have a substituent selected from the substituents S as a substituent.
  • the preferred groups, more preferred groups, even more preferred groups, particularly preferred groups, and most preferred groups of the substituents that may be had are the same as the preferred groups in the substituents S.
  • Ring A1 represents an aromatic hydrocarbon ring structure which may have a substituent or an aromatic heterocyclic structure which may have a substituent.
  • the aromatic hydrocarbon ring is preferably an aromatic hydrocarbon ring having a carbon number of 6 to 30.
  • a benzene ring, a naphthalene ring, an anthracene ring, a triphenylyl ring, an acenaphthene ring, a fluoranthene ring, and a fluorene ring are preferred.
  • the aromatic heterocycle is preferably an aromatic heterocycle having 3 to 30 carbon atoms and containing a nitrogen atom, oxygen atom, or sulfur atom as a heteroatom, more preferably a furan ring, a benzofuran ring, a thiophene ring, or a benzothiophene ring.
  • Ring A1 is more preferably a benzene ring, a naphthalene ring, or a fluorene ring, particularly preferably a benzene ring or a fluorene ring, and most preferably a benzene ring.
  • Ring A2 represents an aromatic heterocyclic structure which may have a substituent.
  • the aromatic heterocycle is preferably an aromatic heterocycle having 3 to 30 carbon atoms and containing a nitrogen atom, an oxygen atom, or a sulfur atom as a heteroatom. Specific examples thereof include a pyridine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, an imidazole ring, an oxazole ring, a thiazole ring, a benzothiazole ring, a benzoxazole ring, a benzimidazole ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, a quinazoline ring, a naphthyridine ring, and a phenanthridine ring.
  • a pyridine ring, a pyrazine ring, a pyrimidine ring, an imidazole ring, a benzothiazole ring, a benzoxazole ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, and a quinazoline ring are preferred
  • a pyridine ring, an imidazole ring, a benzothiazole ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, and a quinazoline ring are more preferred
  • a pyridine ring, an imidazole ring, a benzothiazole ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, and a quinazoline ring are most preferred.
  • Preferred combinations of ring A1 and ring A2, expressed as (ring A1-ring A2) include (benzene ring-pyridine ring), (benzene ring-quinoline ring), (benzene ring-quinoxaline ring), (benzene ring-quinazoline ring), (benzene ring-benzothiazole ring), (benzene ring-imidazole ring), (benzene ring-pyrrole ring), (benzene ring-diazole ring), and (benzene ring-thiophene ring).
  • the substituents which the ring A1 and the ring A2 may have can be arbitrarily selected, but are preferably one or more kinds of substituents selected from the above-mentioned group S of substituents.
  • Ar 201 and Ar 203 each independently represent an aromatic hydrocarbon ring structure which may have a substituent, or an aromatic heterocyclic structure which may have a substituent.
  • Ar 202 represents an aromatic hydrocarbon ring structure which may have a substituent, an aromatic heterocyclic structure which may have a substituent, or an aliphatic hydrocarbon structure which may have a substituent.
  • the aromatic hydrocarbon ring structure is preferably an aromatic hydrocarbon ring having a carbon number of 6 to 30.
  • a benzene ring, a naphthalene ring, an anthracene ring, a triphenylyl ring, an acenaphthene ring, a fluoranthene ring, or a fluorene ring is preferred, a benzene ring, a naphthalene ring, or a fluorene ring is more preferred, and a benzene ring is most preferred.
  • Ar 201 or Ar 202 is a benzene ring which may have a substituent
  • Ar 201 , Ar 202 and Ar 203 is a fluorene ring which may have a substituent
  • the 9- and 9'-positions of the fluorene ring preferably have a substituent or are bonded to an adjacent structure.
  • the aromatic heterocyclic structure is preferably an aromatic heterocyclic ring having 3 to 30 carbon atoms containing any of a nitrogen atom, an oxygen atom or a sulfur atom as a heteroatom, and specific examples thereof include a pyridine ring, a pyrimidine ring, a pyrazine ring, a triazine ring, an imidazole ring, an oxazole ring, a thiazole ring, a benzothiazole ring, a benzoxazole ring, a benzimidazole ring, a quinoline ring, an isoquinoline ring, a quinoxaline ring, a quinazoline ring, a naphthyridine ring, a phenanthridine ring, a carbazole ring, a dibenzofuran ring and a di
  • Ar 202 is an aliphatic hydrocarbon structure which may have a substituent, it is an aliphatic hydrocarbon structure having a straight chain, branched chain, or cyclic structure, and preferably has 1 or more and 24 or less carbon atoms, more preferably has 1 or more and 12 or less carbon atoms, and still more preferably has 1 or more and 8 or less carbon atoms.
  • Each of i1 and i2 independently represents an integer of 0 to 12, preferably 1 to 12, more preferably 1 to 8, and even more preferably 1 to 6. Within this range, improvement in solubility and charge transportability can be expected.
  • i3 preferably represents an integer of 0 to 5, more preferably 0 to 2, and even more preferably 0 or 1.
  • i4 preferably represents an integer of 0 to 2, and more preferably 0 or 1.
  • k1 and k2 each independently represent an integer of preferably 0 to 3, more preferably 1 to 3, even more preferably 1 or 2, and particularly preferably 1.
  • the substituents that Ar 201 , Ar 202 , and Ar 203 may have can be arbitrarily selected, but are preferably one or more substituents selected from the above-mentioned substituent group S, and the preferred groups are also the same as those in the above-mentioned substituent group S, but are more preferably unsubstituted (hydrogen atom), alkyl group, or aryl group, particularly preferably unsubstituted (hydrogen atom) or alkyl group, and most preferably unsubstituted (hydrogen atom) or tertiary butyl group, and it is preferable that the tertiary butyl group is substituted on Ar 203 when Ar 203 is present, on Ar 202 when Ar 203 is not present, and on Ar 201 when Ar 202 and Ar 203 are not present.
  • the compound represented by formula (3) is preferably a compound that satisfies one or more of the following (I) to (IV):
  • the structure represented by formula (b) is preferably a structure having a group linked to a benzene ring, i.e., a benzene ring structure, i1 being 1 to 6, and at least one of the benzene rings being bonded to an adjacent structure at the ortho-position or meta-position. Such a structure is expected to improve the solubility and the charge transport property.
  • (II) (phenylene)-aralkyl(alkyl)
  • Ar 201 and Ar 202 are benzene ring structures
  • Ar 203 is a biphenyl or terphenyl structure
  • i1 and i2 are 1 to 6
  • i3 is 2
  • j is 2.
  • Such a structure is expected to improve the solubility and the charge transport property.
  • B201 - L200 - B202 The structure represented by B 201 -L 200 -B 202 is preferably a structure represented by the following formula (203) or (204).
  • R 211 , R 212 and R 213 each independently represent a substituent.
  • ring B3 represents an aromatic heterocyclic structure containing a nitrogen atom which may have a substituent. Ring B3 is preferably a pyridine ring.
  • the phosphorescent compound represented by formula (201) is not particularly limited, but preferred examples include the following:
  • M2 represents a metal
  • T represents a carbon atom or a nitrogen atom
  • R92 to R95 each independently represent a substituent. However, when T is a nitrogen atom, R94 and R95 do not exist.
  • M2 include metals selected from Groups 7 to 11 of the periodic table. Among them, preferred are ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum, and gold, and particularly preferred are divalent metals such as platinum and palladium.
  • R 92 and R 93 each independently represent a hydrogen atom, a halogen atom, an alkyl group, an aralkyl group, an alkenyl group, a cyano group, an amino group, an acyl group, an alkoxycarbonyl group, a carboxyl group, an alkoxy group, an alkylamino group, an aralkylamino group, a haloalkyl group, a hydroxyl group, an aryloxy group, an aromatic hydrocarbon group, or an aromatic heterocyclic group.
  • R 94 and R 95 each independently represent a substituent represented by the same examples as R 92 and R 93.
  • R 94 or R 95 does not exist that is directly bonded to T.
  • R 92 to R 95 may further have a substituent.
  • the substituent may be the above-mentioned substituent.
  • any two or more groups among R 92 to R 95 may be bonded to each other to form a ring.
  • the molecular weight of the phosphorescent compound is preferably 5,000 or less, more preferably 4,000 or less, and particularly preferably 3,000 or less.
  • the molecular weight of the phosphorescent compound is preferably 1,200 or more, more preferably 1,400 or more, and even more preferably 1,600 or more. It is believed that within this molecular weight range, the phosphorescent compounds do not aggregate with each other and can be uniformly mixed with the charge transport material, thereby making it possible to obtain a light-emitting layer with high luminous efficiency.
  • the molecular weight of the phosphorescent compound is preferably large in that it has a high Tg, melting point, decomposition temperature, etc., and the phosphorescent compound and the light-emitting layer formed have excellent heat resistance, and is less susceptible to deterioration of film quality due to gas generation, recrystallization, molecular migration, etc., and to an increase in impurity concentration due to thermal decomposition of the material.
  • the molecular weight of the phosphorescent compound is preferably small in that it is easier to purify the organic compound.
  • the organic solvent contained in the composition of the present invention is a volatile liquid component used for forming a layer containing the compound according to an embodiment of the present invention by wet film formation.
  • the organic solvent is not particularly limited as long as it is an organic solvent in which the compound according to the embodiment of the present invention, which is the solute, and the light-emitting material described below can be well dissolved.
  • Preferred organic solvents include, for example, alkanes such as n-decane, cyclohexane, ethylcyclohexane, decalin, and bicyclohexane; aromatic hydrocarbons such as toluene, xylene, mesitylene, phenylcyclohexane (cyclohexylbenzene), tetralin, and methylnaphthalene; halogenated aromatic hydrocarbons such as chlorobenzene, dichlorobenzene, and trichlorobenzene; 1,2-dimethoxybenzene, 1,3-dimethoxybenzene, anisole, phenetole, 2-methoxytoluene, 3-methoxytoluene, 4-methoxytoluene, 2,3-dimethylanisole, 2,4-dimethylanisole, and diphenyl ether.
  • alkanes such as n-decane, cyclohexan
  • aromatic ethers such as phenyl acetate, phenyl propionate, methyl benzoate, ethyl benzoate, propyl benzoate, n-butyl benzoate, and other aromatic esters; alicyclic ketones such as cyclohexanone, cyclooctanone, and fenchone; alicyclic alcohols such as cyclohexanol and cyclooctanol; aliphatic ketones such as methyl ethyl ketone and dibutyl ketone; aliphatic alcohols such as butanol and hexanol; aliphatic ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, and propylene glycol-1-monomethyl ether acetate (PGMEA); and the like.
  • alicyclic ketones such as cyclohexanone, cyclooctanone, and fenchone
  • alkanes, aromatic hydrocarbons, aromatic ethers, and aromatic esters are preferred, aromatic hydrocarbons, aromatic ethers, and aromatic esters are more preferred, and aromatic hydrocarbons and aromatic esters are particularly preferred.
  • aromatic hydrocarbons, aromatic ethers, and aromatic esters are particularly preferred.
  • These organic solvents may be used alone or in any combination and ratio of two or more kinds.
  • 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 380°C or lower, preferably 350°C or lower, more preferably 330°C or lower. If the boiling point of the organic solvent is below this range, the film formation stability may decrease during wet film formation due to solvent evaporation from the composition. If the boiling point of the organic solvent is above this range, the film formation stability may decrease during wet film formation due to solvent remaining after film formation.
  • a uniform coating film can be produced. If there is only one or fewer organic solvents with a boiling point of 150°C or higher, it is believed that a uniform film may not be formed during coating.
  • Organic electroluminescent device has a light-emitting layer formed by using the above-mentioned composition for forming a light-emitting layer according to this embodiment, preferably by a wet film-forming method.
  • the organic electroluminescent element preferably has at least an anode, a cathode, and at least one organic layer between the anode and the cathode on a substrate, and at least one of the organic layers is a layer formed using the composition for forming a light-emitting layer according to this embodiment. It is more preferable that such a layer is formed by a wet film-forming method.
  • the organic layer includes a light-emitting layer, and it is more preferable that this light-emitting layer is a layer formed using the composition for forming a light-emitting layer according to this embodiment.
  • wet film formation method refers to a film formation method, i.e., a coating method that employs a wet film formation method such as spin coating, dip coating, die coating, bar coating, blade coating, roll coating, spray coating, capillary coating, inkjet printing, nozzle printing, screen printing, gravure printing, flexographic printing, etc., and then dries the film formed by these methods to form a film.
  • a coating method that employs a wet film formation method such as spin coating, dip coating, die coating, bar coating, blade coating, roll coating, spray coating, capillary coating, inkjet printing, nozzle printing, screen printing, gravure printing, flexographic printing, etc.
  • FIG. 1 is a schematic cross-sectional view showing a preferred structural example of an organic electroluminescent element 10 according to an embodiment of the present invention.
  • reference numeral 1 denotes a substrate
  • reference numeral 2 denotes an anode
  • reference numeral 3 denotes a hole injection layer
  • reference numeral 4 denotes a hole transport layer
  • reference numeral 5 denotes a light emitting layer
  • reference numeral 6 denotes a hole blocking layer
  • reference numeral 7 denotes an electron transport layer
  • reference numeral 8 denotes an electron injection layer
  • reference numeral 9 denotes a cathode.
  • the materials applied to these structures can be any known material and are not particularly limited, but representative materials and manufacturing methods for each layer are described below as examples. When publications, papers, etc. are cited below, it is assumed that the relevant contents can be applied and adapted as appropriate within the scope of common sense of those skilled in the art.
  • the substrate 1 is a support for the organic electroluminescent element.
  • a quartz or glass plate, a metal plate or metal foil, a plastic film or sheet, etc. are used as the substrate 1.
  • a glass plate; a plate of a transparent synthetic resin such as polyester, polymethacrylate, polycarbonate, polysulfone, etc. are preferable.
  • the gas barrier property of the substrate is large, since the organic electroluminescent element is less likely to be deteriorated by the outside air passing through the substrate. For this reason, a method of ensuring the gas barrier property by providing a dense silicon oxide film or the like on at least one side of the synthetic resin substrate is one of the preferable methods.
  • the anode 2 is an electrode that plays a role of injecting holes into the layers on the light-emitting layer 5 side.
  • the anode 2 is usually composed of a metal such as aluminum, gold, silver, nickel, palladium, or platinum; a metal oxide such as an oxide of indium and/or tin; a metal halide such as copper iodide; carbon black; or a conductive polymer such as poly(3-methylthiophene), polypyrrole, or polyaniline.
  • the anode 2 is usually formed by a method such as sputtering or vacuum deposition.
  • the anode 2 can be formed by dispersing these fine particles in an appropriate binder resin solution and applying the solution onto the substrate 1.
  • a conductive polymer a thin film can be formed directly on the substrate 1 by electrolytic polymerization.
  • the anode 2 can also be formed by coating a conductive polymer on the substrate 1 (Appl. Phys. Lett., Vol. 60, p. 2711, 1992).
  • the anode 2 is usually a single-layer structure, but can also be a laminated structure made of multiple materials if desired.
  • the thickness of the anode 2 may be appropriately selected depending on the required transparency. When transparency is required, it is preferable that the visible light transmittance is usually 60% or more, preferably 80% or more. In this case, 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. When opaqueness is sufficient, the thickness of the anode 2 is arbitrary.
  • a substrate 1 that also functions as the anode 2 may be used. It is also possible to laminate a different conductive material on the above-mentioned anode 2.
  • UV ultraviolet
  • oxygen plasma oxygen plasma
  • argon plasma treatment it is preferable to subject the surface of the anode 2 to ultraviolet (UV)/ozone treatment, oxygen plasma, or argon plasma treatment.
  • the hole injection layer 3 is a layer that transports holes from the anode 2 to the light emitting layer 5.
  • the hole injection layer 3 is usually formed on the anode 2.
  • the method for forming the hole injection layer 3 is not particularly limited and may be a vacuum deposition method or a wet film formation method. From the viewpoint of reducing dark spots, the hole injection layer 3 is preferably formed by a wet film formation method.
  • the hole injection layer is formed by a wet film forming method, it is formed using a composition for forming a hole injection layer.
  • the heating temperature is preferably 120°C or higher, more preferably 150°C or higher, more preferably 180°C or higher, and is preferably 300°C or lower, and more preferably 260°C or lower.
  • the thickness of the hole injection layer 3 is in the range of usually 5 nm or more, preferably 10 nm or more, and usually 1000 nm or less, preferably 500 nm or less.
  • the composition for forming a hole injection layer usually contains a hole transport material and an organic solvent as the constituent materials of the hole injection layer 3.
  • the organic solvent contained in the composition for forming a hole injection layer include the same organic solvents as those exemplified as the organic solvents contained in the composition of the present invention.
  • the hole transport material is generally used in the hole injection layer 3 of an organic electroluminescent element, and may be a high molecular weight compound such as a polymer or a low molecular weight compound such as a monomer as long as it has hole transport properties. However, a high molecular weight compound is preferable.
  • hole transport material a compound having an ionization potential of 4.5 eV to 6.0 eV is preferable in terms of the charge injection barrier from the anode 2 to the hole injection layer 3.
  • hole transport materials include aromatic amine derivatives, phthalocyanine derivatives, porphyrin derivatives, oligothiophene derivatives, polythiophene derivatives, benzylphenyl derivatives, compounds in which a tertiary amine is linked with a fluorene group, hydrazone derivatives, silazane derivatives, silanamine derivatives, phosphamine derivatives, quinacridone derivatives, polyaniline derivatives, polypyrrole derivatives, polyphenylenevinylene derivatives, polythienylenevinylene derivatives, polyquinoline derivatives, polyquinoxaline derivatives, and carbon.
  • the derivative for example, in the case of an aromatic amine derivative, includes an aromatic amine itself and a compound having an aromatic amine as the main skeleton, and may be either a polymer or a monomer.
  • the hole transport material used as the material for the hole injection layer 3 may contain any one of these compounds alone or may contain two or more of them.
  • the combination is arbitrary, but it is preferable to use one or more aromatic tertiary amine polymer compounds in combination with one or more other hole transport materials.
  • aromatic amine compounds are preferred as hole transport materials in terms of their amorphous nature and visible light transmittance, and aromatic tertiary amine compounds are particularly preferred.
  • An aromatic tertiary amine compound is a compound that has an aromatic tertiary amine structure, and also includes compounds that have a group derived from an aromatic tertiary amine.
  • the type of aromatic tertiary amine compound is not particularly limited, but from the viewpoint of uniform light emission due to the surface smoothing effect, a polymer compound (polymerized compound with a series of repeating units) having a weight average molecular weight of 1000 or more and 1,000,000 or less is more preferable.
  • a preferred example of an aromatic tertiary amine polymer compound is a polymer compound having a repeating unit represented by the following formula (51) or (61).
  • Ar 3 represents an aromatic hydrocarbon group or an aromatic heterocyclic group which may have a substituent
  • Ar 4 represents a divalent aromatic hydrocarbon group or a divalent aromatic heterocyclic group which may have a substituent, or a divalent group in which a plurality of the aromatic hydrocarbon groups and aromatic heterocyclic groups are linked together directly or via a linking group.
  • Ar 4 in formula (51) is an aromatic hydrocarbon group or an aromatic heterocyclic group, the plurality of which are linked via a linking group represented by the following formula (52):
  • d represents an integer of 1 to 10
  • R 8 and R 9 each independently represent a hydrogen atom or an optionally substituted alkyl group, aromatic hydrocarbon group, or aromatic heterocyclic group. When a plurality of R 8 and R 9 are present, they may be the same or different.
  • j, k, l, m, n, and p each independently represent an integer of 0 or more, provided that l+m ⁇ 1.
  • Ar 11 , Ar 12 , and Ar 14 each independently represent a divalent aromatic ring group having 30 or less carbon atoms which may have a substituent.
  • Ar 13 represents a divalent aromatic ring group having 30 or less carbon atoms which may have a substituent or a divalent group represented by the following formula (62)
  • Q 11 and Q 12 each independently represent an oxygen atom, a sulfur atom, or a hydrocarbon chain having 6 or less carbon atoms which may have a substituent
  • S 1 to S 4 each independently represent a group represented by the following formula (63).
  • the aromatic ring group referred to here means an aromatic hydrocarbon group and an aromatic heterocyclic group.
  • Examples of the aromatic ring group of Ar 11 , Ar 12 , and Ar 14 include a monocyclic ring, a group having 2 to 6 condensed rings, or a group in which two or more of these aromatic rings are linked together.
  • Specific examples of the aromatic ring group having a monocyclic ring or 2 to 6 condensed rings 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 chrysene ring, a triphenylene ring, an acenaphthene ring, a fluoranthene ring, a fluorene ring, a biphenyl group, a terphenyl group, a quaterphenyl group, a furan ring, a benzofuran
  • divalent group examples include a divalent group derived from a benzene ring, a pyrrolopyrazole ring, a pyrrolopyrrole ring, a thienopyrrole ring, a thienothiophene ring, a furopyrrole ring, a furofuran ring, a thienofuran ring, a benzisoxazole ring, a benzisothiazole ring, a benzimidazole ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinoxaline ring, a phenanthridine ring, a benzimidazole ring, a perimidine ring, a qui
  • a divalent group derived from a benzene ring, a naphthalene ring, a fluorene ring, a pyridine ring or a carbazole ring or a biphenyl group is preferred because it efficiently delocalizes the negative charge and is excellent in stability and heat resistance.
  • Examples of the aromatic ring group for Ar 13 are the same as those for Ar 11 , Ar 12 and Ar 14 .
  • R 11 represents an alkyl group, an aromatic ring group, or a trivalent group consisting of an alkyl group having 40 or less carbon atoms and an aromatic ring group, which may have a substituent.
  • R 12 represents an alkyl group, an aromatic ring group, or a divalent group consisting of an alkyl group having 40 or less carbon atoms and an aromatic ring group, which may have a substituent.
  • Ar 31 represents a monovalent aromatic ring group or a monovalent bridging group, which may have a substituent.
  • q represents 1 to 4. When q is 2 or more, multiple R 12 may be the same or different, and multiple Ar 31 may be the same or different.
  • An asterisk (*) indicates the bonding position with the nitrogen atom in formula (61).
  • the aromatic ring group for R 11 is preferably one aromatic ring group which is a monocyclic or fused ring having 3 to 30 carbon atoms, or a group in which 2 to 6 of these are linked together.
  • Specific examples include a benzene ring, a fluorene ring, a naphthalene ring, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, and a trivalent group derived from a group in which 2 to 6 of these are linked together.
  • the alkyl group for R 11 is preferably a linear, branched, or cyclic alkyl group having from 1 to 12 carbon atoms, and specific examples include groups derived from methane, ethane, propane, isopropane, butane, isobutane, pentane, hexane, and octane.
  • the group consisting of an alkyl group having 40 or less carbon atoms and an aromatic ring group for R 11 preferably includes a group in which a linear, branched, or cyclic alkyl group having from 1 to 12 carbon atoms is linked to one or a group in which 2 to 6 aromatic ring groups are linked, each of which is a monocyclic or condensed ring having from 3 to 30 carbon atoms.
  • aromatic ring group of R 12 examples include a divalent group derived from a benzene ring, a fluorene ring, a naphthalene ring, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, and a connecting ring having 30 or less carbon atoms formed by connecting these rings.
  • alkyl group of R 12 include divalent groups derived from methane, ethane, propane, isopropane, butane, isobutane, pentane, hexane, and octane.
  • aromatic ring group of Ar 31 examples include a benzene ring, a fluorene ring, a naphthalene ring, a carbazole ring, a dibenzofuran ring, a dibenzothiophene ring, and a monovalent group derived from a connecting ring having 30 or less carbon atoms formed by connecting these rings.
  • Preferred examples of the structure of formula (62) include the following structures, and the benzene ring or fluorene ring in the main chain in the following structure, which is a partial structure of R 11 , may further have a substituent.
  • Examples of the bridging group of Ar 31 include groups derived from a benzocyclobutene ring, a naphthocyclobutene ring, or an oxetane ring, a vinyl group, an acryl group, etc. From the viewpoint of the stability of the compound, a group derived from a benzocyclobutene ring or a naphthocyclobutene ring is preferred.
  • x and y represent integers of 0 or more.
  • Ar 21 and Ar 23 each independently represent a divalent aromatic ring group, which may have a substituent.
  • Ar 22 represents a monovalent aromatic ring group which may have a substituent, and R 13 represents an alkyl group, an aromatic ring group, or a divalent group consisting of an alkyl group and an aromatic ring group, which may have a substituent.
  • Ar 32 represents a monovalent aromatic ring group or a monovalent bridging group, and these groups may have a substituent.
  • An asterisk (*) indicates the bonding position to the nitrogen atom in formula (61). Examples of the aromatic ring group for Ar 21 and Ar 23 are the same as those for Ar 11 , Ar 12 and Ar 14 .
  • Examples of the aromatic ring group of Ar 22 and Ar 32 include a single ring, 2 to 6 condensed rings, or a group in which two or more of these aromatic rings are linked together. Specific 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 chrysene ring, a triphenylene ring, an acenaphthene ring, a fluoranthene ring, a fluorene ring, a biphenyl group, a terphenyl group, a quaterphenyl group, a furan ring, a benzofuran ring, a thiophene ring, a benzothiophene ring, a pyrrole ring, a pyr
  • Examples of the monovalent group include a pyrazole ring, a pyrrolopyrrole ring, a thienopyrrole ring, a thienothiophene ring, a furopyrrole ring, a furofuran ring, a thienofuran ring, a benzisoxazole ring, a benzisothiazole ring, a benzimidazole ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a cinnoline ring, a quinoxaline ring, a phenanthridine ring, a benzimidazole ring, a perimidine ring, a quinazoline ring, a quinazolinone ring or an
  • a monovalent group derived from a benzene ring, a naphthalene ring, a fluorene ring, a pyridine ring or a carbazole ring or a biphenyl group is preferable because it efficiently delocalizes negative charges and has excellent stability and heat resistance.
  • Examples of the alkyl group or aromatic ring group for R 13 are the same as those for R 12 .
  • the bridging group of Ar 32 is not particularly limited, but preferred examples include groups derived from a benzocyclobutene ring, a naphthocyclobutene ring, or an oxetane ring, a vinyl group, an acryl group, and the like.
  • the above Ar 11 to Ar 14 , R 11 to R 13 , Ar 21 to Ar 23 , Ar 31 to Ar 32 , Q 11 and Q 12 may further have a substituent, provided that it is not contrary to the spirit of the present invention.
  • the molecular weight of the substituent is preferably 400 or less, and more preferably 250 or less.
  • the type of the substituent is not particularly limited, and examples include one or more types selected from the following substituent group W.
  • Substituent group W alkyl groups having 1 or more carbon atoms, preferably 10 or less, and more preferably 8 or less, such as a methyl group or an ethyl group; alkenyl groups having 2 or more carbon atoms, preferably 11 or less, and more preferably 5 or less, such as a vinyl group; alkynyl groups having 2 or more carbon atoms, preferably 11 or less, and more preferably 5 or less, such as an ethynyl group; alkoxy groups having 1 or more carbon atoms, preferably 10 or less, and more preferably 6 or less, such as a methoxy group or an ethoxy group; aryloxy groups having 4 or more carbon atoms, preferably 5 or more, and preferably 25 or less, and more preferably 14 or less, such as a phenoxy group, a naphthoxy group or a pyridyloxy group; Alkoxycarbonyl groups having 2 or more carbon atoms, preferably 11 or less,
  • an alkyl group or an alkoxy group is preferred from the viewpoint of improving solubility, and an aromatic hydrocarbon group or an aromatic heterocyclic group is preferred from the viewpoint of charge transportability and stability.
  • a polymer compound having a repeating unit represented by the following formula (64) is preferred because it has extremely high hole injection and transport properties.
  • R 21 to R 25 each independently represent an arbitrary substituent. Specific examples of the substituents R 21 to R 25 are the same as the substituents described in the above-mentioned [Substituent group W]. Each of s and t independently represents an integer of 0 to 5. Each of u, v and w independently represents an integer of 0 to 4.
  • aromatic tertiary amine polymeric compounds include polymeric compounds containing repeating units represented by the following formula (65) and/or formula (66).
  • Ar 45 , Ar 47 and Ar 48 each independently represent a monovalent aromatic hydrocarbon group which may have a substituent or a monovalent aromatic heterocyclic group which may have a substituent.
  • Ar 44 and Ar 46 each independently represent a divalent aromatic hydrocarbon group which may have a substituent or a divalent aromatic heterocyclic group which may have a substituent.
  • R 41 to R 43 each independently represent a hydrogen atom or an arbitrary substituent.
  • R 41 to R 43 are preferably a hydrogen atom or a substituent described in the above-mentioned [Substituent group W], and more preferably a hydrogen atom, an alkyl group, an alkoxy group, an amino group, an aromatic hydrocarbon group, or an aromatic heterocyclic group.
  • repeating units represented by formula (65) and formula (66) that can be used in the present invention, but the present invention is not limited to these.
  • the composition for forming the hole injection layer preferably contains an electron accepting compound as a constituent material of the hole injection layer 3 .
  • the electron-accepting compound is preferably a compound having an oxidizing power and an ability to accept one electron from the hole-transporting material.
  • the electron-accepting compound is preferably a compound having an electron affinity of 4.0 eV or more, more preferably a compound having an electron affinity of 5.0 eV or more.
  • electron-accepting compounds include one or more compounds selected from the group consisting of triarylboron compounds, metal halides, Lewis acids, organic acids, onium salts, salts of arylamines and metal halides, and salts of arylamines and Lewis acids.
  • electron-accepting compounds include onium salts substituted with organic groups, such as 4-isopropyl-4'-methyldiphenyliodonium tetrakis(pentafluorophenyl)borate and triphenylsulfonium tetrafluoroborate (WO 2005/089024, WO 2017/164268); high-valence inorganic compounds, such as iron(III) chloride (JP 11-251067 A) and ammonium peroxodisulfate; cyano compounds, such as tetracyanoethylene, and aromatic boron compounds, such as tris(pentafluorophenyl)borane (JP 2003-31365 A); fullerene derivatives; iodine; and sulfonate ions, such as polystyrene sulfonate ions, alkylbenzene sulfonate ions, and camphorsulfonate ions.
  • organic groups such as 4-isopropyl
  • the electron-accepting compound can improve the conductivity of the hole injection layer 3 by oxidizing the hole transport material.
  • the material of the hole injection layer 3 may further contain other components in addition to the above-mentioned hole transport material and electron accepting compound, so long as the effects of the present invention are not significantly impaired.
  • the hole transport layer 4 is a layer that transports holes from the anode 2 to the light emitting layer 5.
  • the hole transport layer 4 is not an essential layer for the organic electroluminescent device according to the embodiment of the present invention. However, when the hole transport layer 4 is provided, the hole transport layer 4 is usually formed on the hole injection layer 3 when the hole injection layer 3 is present, or on the anode 2 when the hole injection layer 3 is not present.
  • the method for forming the hole transport layer 4 is not particularly limited and may be a vacuum deposition method or a wet film formation method. From the viewpoint of reducing dark spots, the hole transport layer 4 is preferably formed by a wet film formation method.
  • the material forming the hole transport layer 4 is preferably one that has high hole transport properties and can efficiently transport injected holes. For this reason, the material forming the hole transport layer 4 is preferably one that has a small ionization potential, is highly transparent to visible light, has a large hole mobility, is highly stable, and is unlikely to generate impurities that can become traps during manufacture or use. In many cases, since the hole transport layer 4 contacts the light-emitting layer 5, it is preferable that it does not quench the light emission from the light-emitting layer 5 or form exciplexes between it and the light-emitting layer 5, thereby reducing efficiency.
  • the material of the hole transport layer 4 may be any material that has been conventionally used as a constituent material of the hole transport layer 4.
  • Examples of the material of the hole transport layer 4 include arylamine derivatives, fluorene derivatives, spiro derivatives, carbazole derivatives, pyridine derivatives, pyrazine derivatives, pyrimidine derivatives, triazine derivatives, quinoline derivatives, phenanthroline derivatives, phthalocyanine derivatives, porphyrin derivatives, silole derivatives, oligothiophene derivatives, condensed polycyclic aromatic derivatives, and metal complexes.
  • Materials for the hole transport layer 4 include, for example, polyvinylcarbazole derivatives, polyarylamine derivatives, polyvinyltriphenylamine derivatives, polyfluorene derivatives, polyarylene derivatives, polyarylene ether sulfone derivatives containing tetraphenylbenzidine, polyarylene vinylene derivatives, polysiloxane derivatives, polythiophene derivatives, poly(p-phenylene vinylene) derivatives, etc. These may be alternating copolymers, random polymers, block polymers, or graft copolymers. They may also be polymers with branches in the main chain and three or more terminals, or so-called dendrimers.
  • polyarylamine derivatives and polyarylene derivatives are preferable as the material for the hole transport layer 4 .
  • Specific examples of the polyarylamine derivatives and polyarylene derivatives include those described in JP-A-2008-98619.
  • As the polyarylamine derivative it is preferable to use the aromatic tertiary amine polymer compound.
  • the layer is wet-formed in the same manner as in the formation of the hole injection layer 3, and then dried.
  • the composition for forming the hole transport layer contains an organic solvent in addition to the above-mentioned hole transport material.
  • the organic solvent used is the same as that used in the composition for forming the hole injection layer.
  • the drying conditions are also the same as those in the case of forming the hole injection layer 3.
  • the deposition conditions are the same as those for forming the hole injection layer 3.
  • the 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 200 nm or less, taking into consideration factors such as the penetration of the low molecular weight material in the light emitting layer and the swelling of the hole transport material.
  • the light-emitting layer 5 is a layer that becomes a main light-emitting source when excited by recombination of holes injected from the anode 2 and electrons injected from the cathode 9 between the electrodes to which an electric field is applied.
  • the light-emitting layer 5 is usually formed on the hole-transport layer 4 when the hole-transport layer 4 is present, on the hole-injection layer 3 when the hole-transport layer 4 is not present and the hole-injection layer 3 is present, and on the anode 2 when neither the hole-transport layer 4 nor the hole-injection layer 3 is present.
  • 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. As described above, the light-emitting layer 5 of the organic electroluminescent device according to the embodiment of the present invention is preferably formed using the light-emitting layer-forming composition according to this embodiment.
  • the inkjet method is preferred as a wet film formation method for forming the light-emitting layer 5.
  • the inkjet method By forming the light-emitting layer 5 by the inkjet method, it is possible to form a film by the inkjet method in succession to the organic layer formed using the layer-forming composition according to the embodiment of the present invention, which is preferable.
  • the thickness of the light-emitting layer 5 is arbitrary.
  • the thickness of the light-emitting layer 5 is usually 5 nm or more, preferably 10 nm or more, and usually 100 nm or less, preferably 90 nm or less.
  • a hole blocking layer 6 may be provided between the light emitting layer 5 and an electron injection layer 8 described later.
  • the hole blocking layer 6 is a layer of the electron transport layer that also plays a role of blocking holes moving from the anode 2 from reaching the cathode 9.
  • the hole blocking layer 6 is a layer laminated on the light emitting layer 5 so as to be in contact with the interface of the light emitting layer 5 on the cathode 9 side.
  • the hole blocking layer 6 has the role of preventing holes moving from the anode 2 from reaching the cathode 9, and the role of efficiently transporting electrons injected from the cathode 9 in the direction of the light-emitting layer 5.
  • the physical properties required for the material constituting the hole blocking layer 6 include high electron mobility and low hole mobility, a large energy gap (difference between HOMO and LUMO), and a high excited triplet energy level (T1).
  • materials for the hole blocking layer 6 that satisfy these conditions include mixed ligand complexes such as bis(2-methyl-8-quinolinolato)(phenolato)aluminum and bis(2-methyl-8-quinolinolato)(triphenylsilanolate)aluminum; metal complexes such as bis(2-methyl-8-quinolinolato)aluminum- ⁇ -oxo-bis-(2-methyl-8-quinolinolato)aluminum binuclear metal complex; styryl compounds such as distyrylbiphenyl derivatives (Japanese Patent Laid-Open No.
  • the thickness of the hole blocking layer 6 is arbitrary.
  • the thickness of the hole blocking layer 6 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 7 is a layer provided between the light emitting layer 5 and the cathode 9 for transporting electrons.
  • the electron transporting compound for the electron transport layer 7 a compound is usually used which has a high efficiency of electron injection from the cathode 9 or an adjacent layer on the cathode 9 side, and has high electron mobility so that the injected electrons can be efficiently transported.
  • Examples of compounds that satisfy such conditions include metal complexes such as aluminum complexes and lithium complexes of 8-hydroxyquinoline (JP-A-59-194393), metal complexes of 10-hydroxybenzo[h]quinoline, oxadiazole derivatives, distyrylbiphenyl derivatives, silole derivatives, 3-hydroxyflavone metal complexes, 5-hydroxyflavone metal complexes, benzoxazole metal complexes, benzothiazole metal complexes, trisbenzimidazolylbenzene (U.S. Pat. No.
  • the hole blocking layer 6 is not present, and the layer in contact with the cathode 9 side of the light-emitting layer 5 is the electron transport layer 7.
  • the thickness of the electron transport layer 7 is arbitrary as long as it does not significantly impair the effects of the present invention.
  • the thickness of the electron transport layer 7 is usually 1 nm or more, preferably 5 nm or more, and is usually 300 nm or less, preferably 100 nm or less.
  • an electron injection layer 8 may be provided between the electron transport layer 7 and the cathode 9 described below.
  • the electron injection layer 8 is made of an inorganic salt or the like. Examples of materials for the electron injection layer 8 include lithium fluoride (LiF), magnesium fluoride (MgF 2 ), lithium oxide (Li 2 O), and cesium (II) carbonate (CsCO 3 ) (see Applied Physics Letters, 1997, Vol. 70, pp. 152; Japanese Patent Publication No. 10-74586; IEEE Transactions on Electron Devices, 1997, Vol. 44, pp. 1245; SID 04 Digest, pp. 154, etc.).
  • the electron injection layer 8 since the electron injection layer 8 often does not have charge transport properties, it is preferable to use it as an extremely thin film in order to efficiently inject electrons, and the film thickness is usually 0.1 nm or more, and preferably 5 nm or less.
  • the cathode 9 is an electrode that serves to inject electrons into the layers on the light-emitting layer 5 side.
  • Examples of materials for the cathode 9 include metals such as aluminum, gold, silver, nickel, palladium, and platinum, metal oxides such as indium and/or tin oxide, metal halides such as copper iodide, carbon black, and conductive polymers such as poly(3-methylthiophene), polypyrrole, and polyaniline.
  • metals with a low work function are preferred for efficient electron injection, and suitable metals such as tin, magnesium, indium, calcium, aluminum, and silver, or alloys thereof are used.
  • Specific examples include alloy electrodes with a low work function, such as a magnesium-silver alloy, a magnesium-indium alloy, and an aluminum-lithium alloy.
  • the material for the cathode 9 may be of one type alone or of two or more types in any combination and ratio.
  • the thickness of the cathode 9 varies depending on the transparency required. When transparency is required, it is preferable that the visible light transmittance is usually 60% or more, and preferably 80% or more. In this case, the thickness of the cathode 9 is usually 5 nm or more, preferably 10 nm or more, and usually 1000 nm or less, preferably 500 nm or less. When opacity is sufficient, the thickness of the cathode 9 is arbitrary, and the cathode may be the same as the substrate.
  • a different conductive material on top of the cathode 9 .
  • a cathode made of a metal having a low work function such as an alkali metal such as sodium or cesium, or an alkaline earth metal such as barium or calcium
  • metals such as aluminum, silver, copper, nickel, chromium, gold, platinum, etc. These materials may be used alone or in any combination and ratio of two or more.
  • the organic electroluminescent device according to the embodiment of the present invention may have another configuration without departing from the spirit of the device.
  • any layer may be provided between the anode 2 and the cathode 9 in addition to the layers described above, and any layer not essential among the layers described above may be omitted, so long as the performance is not impaired.
  • the other components may be provided on the substrate 1 in the following order: cathode 9, electron injection layer 8, electron transport layer 7, hole blocking layer 6, light-emitting layer 5, hole transport layer 4, hole injection layer 3, and anode 2.
  • the organic electroluminescent device according to the embodiment of the present invention may be configured as a single organic electroluminescent device, may be applied to a configuration in which multiple organic electroluminescent devices are arranged in an array, or may be applied to a configuration in which anodes and cathodes are arranged in an XY matrix.
  • Each layer described above may contain ingredients other than those described as materials.
  • the method for producing the organic electroluminescence element according to the present embodiment is not particularly limited as long as it uses the composition for forming the light-emitting layer as described above.
  • the method for producing the organic electroluminescence element according to the present embodiment may include a production method including a step of forming a light-emitting layer by a wet film-forming method using the composition for forming the light-emitting layer as described above.
  • the display device according to the present embodiment has the organic electroluminescent device as described above.
  • the type or structure of the display device there are no particular limitations on the type or structure of the display device, and it can be assembled in a conventional manner using the organic electroluminescent device according to the present embodiment.
  • the display device according to this embodiment can be formed by a method such as that described in "Organic EL Display” (Ohmsha, published on August 20, 2004, by Tokito Shizuo, Adachi Chinaya, and Murata Hideyuki).
  • Example 1 An organic electroluminescent device was prepared in the following manner. A transparent conductive film of indium tin oxide (ITO) was deposited to a thickness of 50 nm on a glass substrate (a sputter-formed product manufactured by Geomatec Co., Ltd.) and patterned into 2 mm-wide stripes using normal photolithography and hydrochloric acid etching to form an anode. The substrate on which the ITO pattern was thus formed was ultrasonically cleaned with a surfactant aqueous solution, rinsed with ultrapure water, ultrasonically cleaned with ultrapure water, and rinsed with ultrapure water, in that order, then dried with compressed air, and finally cleaned with ultraviolet ozone.
  • ITO indium tin oxide
  • composition for forming a hole injection layer a composition was prepared by dissolving 3.0% by mass of a hole transporting polymer compound having a repeating structure represented by the following formula (P-1) and 0.6% by mass of an electron accepting compound represented by the following formula (HI-1) in ethyl benzoate.
  • This solution was spin-coated onto the substrate in the atmosphere and dried on a hot plate in the atmosphere at 240°C for 30 minutes to form a uniform thin film with a thickness of 40 nm, which served as the hole injection layer.
  • a charge transporting polymer compound having a structure represented by the following formula (HT-1) was dissolved in mesitylene to prepare a 2.0% by mass solution.
  • This solution was spin-coated in a nitrogen glove box onto the substrate on which the hole injection layer had been formed, and dried for 30 minutes at 230° C. on a hot plate in the nitrogen glove box to form a uniform thin film with a thickness of 40 nm, which was used as a hole transport layer.
  • This composition for forming the light-emitting layer was spin-coated in a nitrogen glove box onto the substrate on which the hole transport layer had been applied, and then dried for 20 minutes at 120°C on a hot plate in the nitrogen glove box to form a uniform thin film with a thickness of 60 nm, which served as the light-emitting layer.
  • the substrate on which the light-emitting layer had been formed was placed in a vacuum deposition apparatus, and the inside of the apparatus was evacuated until the pressure became 2 ⁇ 10 ⁇ 4 Pa or less.
  • a compound represented by the following formula (HB-1) and 8-hydroxyquinolinolatolithium were co-deposited on the light-emitting layer at a rate of 1 ⁇ /sec by vacuum deposition so that the thickness ratio was 2:3, forming a hole-blocking layer with a thickness of 30 nm.
  • a 2 mm wide striped shadow mask was attached to the substrate as a mask for cathode deposition so that it was perpendicular to the ITO stripes of the anode, and placed in another vacuum deposition device.
  • Aluminum was then heated in a molybdenum boat to form an 80 nm thick aluminum layer at a deposition rate of 1 to 8.6 ⁇ /sec, forming the cathode.
  • the organic electroluminescent devices (Examples 1 and 2) in which the compounds (H-2) and (H-6) according to this embodiment are used as charge transport hosts in the composition for forming the light-emitting layer were found to have higher luminous efficiency than the organic electroluminescent devices (Comparative Examples 1 and 2) in which the compounds (H-3) and (H-4) are used in the composition for forming the light-emitting layer.
  • the organic electroluminescent device (Examples 1 and 2) in which the compound (H-1) according to this embodiment is used in the composition for forming the light-emitting layer as a host to be combined with the compounds (H-2) and (H-6) according to this embodiment is used in the composition for forming the light-emitting layer, was found to have a higher light-emitting efficiency than the organic electroluminescent device (Comparative Example 3 and Comparative Example 4) in which the compound (H-5) is used in the composition for forming the light-emitting layer.
  • Example 3 and Comparative Examples 4 and 5 were measured for current luminous efficiency (cd/A) when emitting light at 1,000 cd/ m2 .
  • the organic electroluminescent device (Examples 3 and 4) in which the compound (H-7) according to this embodiment is used in the composition for forming the light-emitting layer as a host to be combined with the compounds (H-2) and (H-6) according to this embodiment is found to have a higher light-emitting efficiency than the organic electroluminescent device (Comparative Example 5) in which the compound (H-8) is used in the composition for forming the light-emitting layer.
  • Example 5 and Comparative Examples 6 to 8 were measured for current luminous efficiency (cd/A) when emitting light at 1,000 cd/ m2 .
  • the organic electroluminescent device (Example 5) in which the compound (H-6) according to this embodiment is used as a charge transport host in the composition for forming the light-emitting layer was found to have a higher light-emitting efficiency than the organic electroluminescent device (Comparative Example 7 and Comparative Example 8) in which the compounds (H-3) and (H-10) are used in the composition for forming the light-emitting layer.
  • the organic electroluminescent device (Example 5) in which the compound (H-7) according to this embodiment is used in the composition for forming the light-emitting layer as a host to be combined with the compound (H-6) according to this embodiment is found to have a higher light-emitting efficiency than the organic electroluminescent device (Comparative Example 6) in which the compound (H-9) is used in the composition for forming the light-emitting layer.
  • Example 6 and Comparative Example 9 were measured for current luminous efficiency (cd/A) when emitting light at 1,000 cd/ m2 .
  • the organic electroluminescent device (Example 6) in which the compound (H-7) according to this embodiment is used in the composition for forming the light-emitting layer as a host to be combined with the compound (H-6) according to this embodiment is found to have a higher light-emitting efficiency than the organic electroluminescent device (Comparative Example 9) in which the compound (H-9) is used in the composition for forming the light-emitting layer.
  • composition for forming a light-emitting layer according to the embodiment of the present invention makes it possible to produce an organic electroluminescent device that exhibits excellent device characteristics and has particularly high light-emitting efficiency.

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Abstract

La présente invention aborde le problème de la fourniture d'une composition destinée à former une couche électroluminescente pour la production d'un élément électroluminescent organique qui présente une efficacité lumineuse plus élevée que jamais auparavant, la composition permettant la production d'un élément électroluminescent organique de préférence par un procédé de formation de film humide. La présente invention concerne : une composition pour former une couche électroluminescente d'un élément électroluminescent organique, la composition contenant au moins un composé cyclique hétéroaromatique qui présente une structure spécifique, un composé indolocarbazole qui présente une structure spécifique, un matériau électroluminescent et un solvant organique ; un procédé de production d'un élément électroluminescent organique, le procédé comprenant une étape dans laquelle une couche électroluminescente est formée par un procédé de formation de film humide à l'aide de cette composition pour former une couche électroluminescente ; et un élément électroluminescent organique qui comprend une couche électroluminescente qui est formée à l'aide de cette composition pour former une couche électroluminescente.
PCT/JP2023/042479 2022-11-30 2023-11-28 Composition pour former une couche électroluminescente d'élément électroluminescent organique, élément électroluminescent organique et son procédé de production, et dispositif d'affichage Ceased WO2024117109A1 (fr)

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007126443A (ja) * 2005-10-07 2007-05-24 Mitsubishi Chemicals Corp 炭化水素化合物、電荷輸送材料、電荷輸送材料組成物および有機電界発光素子
JP5163837B2 (ja) * 2011-01-11 2013-03-13 三菱化学株式会社 有機電界発光素子用組成物、有機電界発光素子、表示装置及び照明装置
JP2014509068A (ja) * 2010-12-20 2014-04-10 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 電子技術応用のための電気活性組成物
JP2018009078A (ja) * 2016-07-12 2018-01-18 三星電子株式会社Ｓａｍｓｕｎｇ Ｅｌｅｃｔｒｏｎｉｃｓ Ｃｏ．，Ｌｔｄ． 有機発光素子用インキ組成物、並びにこれを用いた有機発光素子およびその製造方法
WO2018135656A1 (fr) * 2017-01-23 2018-07-26 三菱ケミカル株式会社 Composition pour former une couche électroluminescente et élément électroluminescent organique contenant ladite composition pour former une couche électroluminescente
KR20190038109A (ko) * 2017-09-29 2019-04-08 삼성에스디아이 주식회사 유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치
US20210111350A1 (en) * 2017-05-26 2021-04-15 Samsung Sdi Co., Ltd. Phosphorescent host composition, organic optoelectronic diode, and display device
US20220255020A1 (en) * 2021-02-04 2022-08-11 Universal Display Corporation Organic electroluminescent materials and devices

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007126443A (ja) * 2005-10-07 2007-05-24 Mitsubishi Chemicals Corp 炭化水素化合物、電荷輸送材料、電荷輸送材料組成物および有機電界発光素子
JP2014509068A (ja) * 2010-12-20 2014-04-10 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー 電子技術応用のための電気活性組成物
JP5163837B2 (ja) * 2011-01-11 2013-03-13 三菱化学株式会社 有機電界発光素子用組成物、有機電界発光素子、表示装置及び照明装置
JP2018009078A (ja) * 2016-07-12 2018-01-18 三星電子株式会社Ｓａｍｓｕｎｇ Ｅｌｅｃｔｒｏｎｉｃｓ Ｃｏ．，Ｌｔｄ． 有機発光素子用インキ組成物、並びにこれを用いた有機発光素子およびその製造方法
WO2018135656A1 (fr) * 2017-01-23 2018-07-26 三菱ケミカル株式会社 Composition pour former une couche électroluminescente et élément électroluminescent organique contenant ladite composition pour former une couche électroluminescente
US20210111350A1 (en) * 2017-05-26 2021-04-15 Samsung Sdi Co., Ltd. Phosphorescent host composition, organic optoelectronic diode, and display device
KR20190038109A (ko) * 2017-09-29 2019-04-08 삼성에스디아이 주식회사 유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치
US20220255020A1 (en) * 2021-02-04 2022-08-11 Universal Display Corporation Organic electroluminescent materials and devices

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