WO2022230574A1 - Matériau de transport de charge, composition et élément luminescent organique - Google Patents

Matériau de transport de charge, composition et élément luminescent organique Download PDF

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WO2022230574A1
WO2022230574A1 PCT/JP2022/015885 JP2022015885W WO2022230574A1 WO 2022230574 A1 WO2022230574 A1 WO 2022230574A1 JP 2022015885 W JP2022015885 W JP 2022015885W WO 2022230574 A1 WO2022230574 A1 WO 2022230574A1
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atoms
substituted
adjacent
compound
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PCT/JP2022/015885
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Japanese (ja)
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寛晃 小澤
勇人 垣添
桃子 森尾
亜衣子 後藤
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株式会社Kyulux
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Priority claimed from JP2021140203A external-priority patent/JP2022168813A/ja
Application filed by 株式会社Kyulux filed Critical 株式会社Kyulux
Priority to CN202280030927.2A priority Critical patent/CN117279919A/zh
Priority to KR1020237037437A priority patent/KR20240004404A/ko
Publication of WO2022230574A1 publication Critical patent/WO2022230574A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • 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
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • 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
    • H10K2101/20—Delayed fluorescence emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to a compound useful as a charge transport material, a composition using the compound, and an organic light-emitting device.
  • organic electroluminescence elements organic electroluminescence elements
  • various attempts have been made to improve the luminous efficiency by newly developing and combining electron transporting materials, hole transporting materials, light emitting materials, host materials, and the like, which constitute organic electroluminescence elements.
  • an organic electroluminescence device using a delayed fluorescence material has been developed and is attracting attention (see Non-Patent Document 1).
  • a delayed fluorescence material is a material that emits fluorescence when returning from the excited singlet state to the ground state after reverse intersystem crossing from the excited triplet state to the excited singlet state occurs in the excited state. Fluorescence by such a pathway is called delayed fluorescence because it is observed later than the fluorescence from the excited singlet state directly generated from the ground state (ordinary fluorescence).
  • the probability of occurrence of an excited singlet state and an excited triplet state is statistically 25%:75%. There is a limit to the improvement in luminous efficiency with only the fluorescence of .
  • the delayed fluorescence material not only the excited singlet state but also the excited triplet state can be used for fluorescence emission through the reverse intersystem crossing described above, so the emission is higher than that of ordinary fluorescent materials. Efficiency will be obtained.
  • a delayed fluorescence material having such characteristics is generally used together with a host material in the light-emitting layer of an organic electroluminescence device, and actually contributes to the improvement of the light-emitting efficiency.
  • a compound with a higher lowest excited singlet energy than the delayed fluorescent material is selected as the host material to be combined with the delayed fluorescent material.
  • a host material that has been used in combination with a conventional fluorescent material that does not emit delayed fluorescence is combined with a delayed fluorescent material as it is, it is not possible to achieve sufficient light emission performance.
  • device characteristics such as driving voltage.
  • the inventors of the present invention conducted studies with the aim of improving the device characteristics of an organic light-emitting device using a delayed fluorescence material.
  • the present inventors found that a compound having a specific structure is useful as a charge transport material such as a host material.
  • the present invention has been proposed based on these findings, and specifically has the following configurations.
  • D-Ar-Z A compound represented by the following general formula (1).
  • D represents a donor group
  • Ar is a substituted or unsubstituted arylene group, or a substituted or unsubstituted biphenylylene group (provided that the two benzene rings constituting the biphenylylene group are may be further linked via a linking group)
  • Z is a substituted or unsubstituted benzophlodibenzofuryl group, a substituted or unsubstituted benzophlodibenzothienyl group, a substituted or unsubstituted benzothienodibenzofuryl group , or represents a substituted or unsubstituted benzothienodibenzothienyl group.
  • n 0 or 1; n1, n2, n3, n4, n5 and n7 each independently represents an integer of 0 to 4; n6 represents an integer of 0 to 2; R 3 and R 4 , 2 adjacent R 1 , 2 adjacent R 2 , 2 adjacent R 3 , 2 adjacent R 4 , 2 adjacent R 5 , 2 adjacent R 6 and two adjacent R 7 may combine with each other to form a cyclic structure.
  • the compound according to [1] represented by any one of the following general formulas (3-1) to (3-16).
  • R 1 to R 7 each independently represent a deuterium atom or a substituent.
  • n 0 or 1
  • n1, n2, n3, n4, n5 and n7 each independently represents an integer of 0 to 4
  • n3′ and n4′ each independently represents an integer of 0 to 3 represents an integer
  • n6 represents any integer from 0 to 2.
  • R 3 and R 4 , 2 adjacent R 1 , 2 adjacent R 2 , 2 adjacent R 3 , 2 adjacent R 4 , 2 adjacent R 5 , 2 adjacent R 6 and two adjacent R 7 may combine with each other to form a cyclic structure.
  • [5] no two adjacent R 1 's are bonded together to form a cyclic structure, and no two adjacent R 2 's are bonded together to form a cyclic structure, [3] Or the compound according to [4].
  • [6] The compound according to any one of [3] to [5], wherein neither R 1 nor R 2 contains a carbazole ring structure.
  • [7] A charge transport material comprising the compound according to any one of [1] to [6].
  • [8] The charge-transporting material according to [7], which is a host material.
  • [9] A composition in which a host material comprising the compound according to any one of [1] to [6] is doped with a delayed fluorescence material.
  • the composition according to [9] which is in the form of a film.
  • composition according to [9] or [10], wherein the delayed fluorescence material is a compound having a cyanobenzene structure in which the benzene ring is substituted with one cyano group.
  • the delayed fluorescence material is a compound having a dicyanobenzene structure in which two cyano groups are substituted on the benzene ring.
  • the delayed fluorescence material is a compound having an azabenzene structure in which at least one carbon atom constituting the ring skeleton of the benzene ring is substituted with a nitrogen atom. thing.
  • the compound of the present invention is useful as a charge transport material and can be effectively used in organic semiconductor devices.
  • the device characteristics can be improved by using the compound of the present invention as a host material for the light-emitting layer of an organic electroluminescence device.
  • substituted means an atom or group of atoms other than a hydrogen atom and a deuterium atom.
  • substituted or unsubstituted means that hydrogen atoms may be replaced with deuterium atoms or substituents.
  • Z is a substituted or unsubstituted benzoflodibenzofuryl group, a substituted or unsubstituted benzoflodibenzothienyl group, a substituted or unsubstituted benzothienodibenzofuryl group, or a substituted or unsubstituted benzothieno represents a dibenzothienyl group.
  • Z is attached in a fused ring containing at least one furan structure. In one aspect of the invention, Z is attached in a fused ring containing at least one thiophene structure.
  • Z is linked in a fused ring comprising at least one furan structure and at least one thiophene structure. In one aspect of the invention, Z is attached in a fused ring containing at least one furan structure but no thiophene structure. In one aspect of the invention, Z is linked in a fused ring containing at least one thiophene structure but no furan structures. In one aspect of the invention, Z is attached in a condensed ring with five condensed rings.
  • Z is an unsubstituted benzophodibenzofuryl group, an unsubstituted benzophodibenzothienyl group, an unsubstituted benzothienodibenzofuryl group, or an unsubstituted benzothienodibenzothienyl group.
  • Z is a substituted benzophodibenzofuryl group, a substituted benzophodibenzothienyl group, a substituted benzothienodibenzofuryl group, or a substituted benzothienodibenzothienyl group.
  • Z is a substituted or unsubstituted benzoflodibenzofuryl group. In one aspect of the invention, Z is a substituted or unsubstituted benzoflodibenzothienyl group. In one aspect of the invention, Z is a substituted or unsubstituted benzothienodibenzofuryl group. In one aspect of the invention, Z is a substituted or unsubstituted benzothienodibenzothienyl group.
  • Z is bonded through a benzene ring that constitutes the end of each condensed ring structure of a benzoflodibenzofuryl group, a benzoflodibenzothienyl group, a benzothienodibenzofuryl group, and a benzothienodibenzothienyl group.
  • Z is bonded through a benzene ring that constitutes the central portion of each condensed ring structure of a benzoflodibenzofuryl group, a benzoflodibenzothienyl group, a benzothienodibenzofuryl group, and a benzothienodibenzothienyl group.
  • Z may have any of the following skeletons 1a to 1f.
  • Z has any skeleton of skeletons 1a-1c.
  • Z has the skeleton of any of skeletons 1d-1f.
  • Z has a skeleton of skeleton 1a or 1b.
  • Z has a skeleton of skeleton 1c or 1d.
  • Z has the skeleton of skeleton 1e or 1f.
  • Z has the skeleton of skeleton 1c.
  • Z may have any of the following skeletons 2a to 2f.
  • Z has any of skeletons 2a-2c.
  • Z has the skeleton of any of skeletons 2d-2f.
  • Z has a skeleton of skeleton 2a or 2b.
  • Z has a skeleton of skeleton 2c or 2d.
  • Z has a skeleton of skeleton 2e or 2f.
  • Z has a skeleton of skeleton 2c.
  • Z may have any of the following skeletons 3a to 3f.
  • Z has any of skeletons 3a-3c.
  • Z has a skeleton of any of skeletons 3d-3f.
  • Z has a skeleton of skeleton 3a or 3b.
  • Z has a skeleton of skeleton 3c or 3d.
  • Z has a skeleton of skeleton 3e or 3f.
  • Z has a skeleton of skeleton 3c.
  • Z may have any of the skeletons 4a to 4f below.
  • Z has the skeleton of any of skeletons 4a-4c.
  • Z has the skeleton of any of skeletons 4d-4f.
  • Z has a skeleton of skeleton 4a or 4b.
  • Z has a skeleton of skeleton 4c or 4d.
  • Z has a skeleton of skeleton 4e or 4f.
  • Z has a skeleton of skeleton 4c.
  • the hydrogen atoms in the above skeletons 1a to 4f may be substituted with deuterium atoms or substituents.
  • deuterium atoms or substituents For example, one in which some of the hydrogen atoms bonded to the skeleton are replaced with deuterium atoms, and one in which all of the hydrogen atoms bonded to the skeleton are replaced with deuterium atoms can be exemplified. can.
  • An unsubstituted one can also be preferably employed.
  • the substituent may be selected from substituent group A, may be selected from substituent group B, may be selected from substituent group C, or may be selected from substituent group D. or may be selected from Substituent Group E.
  • Z has any one of skeletons 1a, 2a, 3a and 4a. In one aspect of the invention, Z has the skeleton of any of skeletons 1b, 2b, 3b, 4b. In one aspect of the invention, Z has the skeleton 1c, 2c, 3c, 4c. In one aspect of the invention, Z has the skeleton 1d, 2d, 3d, 4d. In one aspect of the invention, Z has the skeleton 1e, 2e, 3e, 4e. In one aspect of the invention, Z has the skeleton 1f, 2f, 3f, or 4f. In one aspect of the invention, the skeletons 1a-4f have no further fused rings. In one aspect of the invention, the skeletons 1a-4f are further fused with rings. For example, a benzene ring, benzofuro structure, and benzothieno structure may be condensed.
  • Ar represents a substituted or unsubstituted arylene group or a substituted or unsubstituted biphenylylene group.
  • arylene group For the description and preferred range of the arylene group, reference can be made to the description and preferred range of the aryl group to be given later.
  • Ar preferably includes a substituted or unsubstituted phenylene group.
  • the phenylene group may be a 1,2-phenylene group, a 1,3-phenylene group or a 1,4-phenylene group, preferably a 1,3-phenylene group or a 1,4-phenylene group.
  • a 1,3-phenylene group or a 1,4-phenylene group may be employed.
  • the biphenylylene group is a linking group in which two phenylene groups are linked, and is any of biphenyl-2,2'-diyl group, biphenyl-3,3'-diyl group and biphenyl-4,4'-diyl group. However, biphenyl-3,3′-diyl group and biphenyl-4,4′-diyl group are preferable. base may be employed. Two benzene rings constituting a biphenylylene group may be further linked to each other via a linking group.
  • a substituted or unsubstituted dibenzofurandyl group is formed by bonding via an oxygen atom (--O--).
  • a dibenzothiophenediyl structure is formed by bonding via a sulfur atom (--S--).
  • Ar has any one of the skeletons below.
  • Ar has a 5a or 5b backbone. In one aspect of the invention, Ar has a backbone of any of 5c-5f. In one aspect of the invention, Ar has a 5c or 5d backbone. In one aspect of the invention, Ar has a 5e or 5f backbone. In one aspect of the invention, Ar has a 5c or 5e backbone. In one aspect of the invention, Ar has a 5d or 5fd backbone.
  • the hydrogen atoms of the arylene group and biphenylylene group that Ar can take, and the hydrogen atoms in skeletons 5a to 5f may be substituted with a deuterium atom or a substituent.
  • substituents include those in which some of the hydrogen atoms are substituted with deuterium atoms, and those in which all of the hydrogen atoms are substituted with deuterium atoms.
  • An unsubstituted one can also be preferably employed.
  • the substituent may be selected from substituent group A, may be selected from substituent group B, may be selected from substituent group C, or may be selected from substituent group D. or may be selected from Substituent Group E.
  • D in the general formula (1) represents a donor group.
  • the donor group referred to herein is a group having a negative Hammett's ⁇ p value.
  • k0 is the rate constant of a benzene derivative without a substituent
  • k is the rate constant of a benzene derivative substituted with a substituent
  • K0 is the equilibrium constant of a benzene derivative without a substituent
  • K is a substituent.
  • the equilibrium constant of the benzene derivative substituted with ⁇ represents the reaction constant determined by the type and conditions of the reaction.
  • a group having a positive Hammett ⁇ p value tends to exhibit electron-withdrawing properties (acceptor properties). Note that in one embodiment of the present invention, the compound represented by General Formula (1) does not contain a substituent having a ⁇ p value of 0.2 or more.
  • the donor group is preferably a group containing a substituted amino group.
  • the substituent bonded to the nitrogen atom of the amino group is preferably a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. , a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, more preferably a substituted or unsubstituted aryl group.
  • the substituted amino group is particularly preferably a substituted or unsubstituted diarylamino group or a substituted or unsubstituted diheteroarylamino group.
  • Two atomic groups bonded to the nitrogen atom of the substituted amino group may bond together to form a cyclic structure.
  • the donor group in the present invention may be a group that binds through the nitrogen atom of the substituted amino group, or a group that binds through the group to which the substituted amino group is bound.
  • the group to which the substituted amino group is bonded is preferably a ⁇ -conjugated group.
  • a group that binds through the nitrogen atom of a substituted amino group or a group that binds the nitrogen atom of the substituted amino group to a benzene ring and binds through the benzene ring, and more preferred is a substituted amino group. It is a group attached at the nitrogen atom of the group.
  • a substituted or unsubstituted carbazol-9-yl group is particularly preferred as the donor group in the present invention.
  • the carbazol-9-yl group may be further condensed with a benzene ring or hetero ring. In one aspect of the invention, the carbazol-9-yl group is not further fused with a benzene ring or a heterocycle.
  • the substituent of the carbazol-9-yl group may be, for example, a substituent selected from the following substituent group A, a substituent selected from the following substituent group B, or a substituent selected from the following substituent group It may be a substituent selected from C, a substituent selected from the following substituent group D, or a substituent selected from the following substituent group E.
  • Preferred carbazol-9-yl groups include an unsubstituted carbazol-9-yl group, a carbazol-9-yl group substituted at least one of the 3- and 6-positions, and a carbazole substituted at both the 3- and 6-positions. -9-yl group can be exemplified.
  • a group represented by the following general formula is employed as the donor group.
  • Ar 1 and Ar 2 each independently represent a phenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenylyl group or m-terphenylyl group.
  • p represents 0 or 1; When p is 1, Ar 1 and Ar 2 may be the same or different.
  • * represents a binding position.
  • a group represented by the following general formula is employed as the donor group.
  • X3 represents an oxygen atom or a sulfur atom.
  • Ar 3 and Ar 4 each independently represent a phenyl group, 2-biphenylyl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenylyl group or m-terphenylyl group.
  • q and r each independently represent 0 or 1, and q+r is 1 or 2; When both q and r are 1, Ar 3 and Ar 4 may be the same or different.
  • * represents a binding position.
  • the donor group that D can take preferably has 13 or more atoms other than hydrogen atoms and deuterium atoms. You can also choose what is The donor group that D can take may be composed only of atoms selected from, for example, a hydrogen atom, a deuterium atom, a carbon atom, a nitrogen atom and an oxygen atom, for example a hydrogen atom, a deuterium atom, a carbon atom and It may be composed only of atoms selected from nitrogen atoms, for example, it may be composed only of atoms selected from hydrogen atoms, carbon atoms and nitrogen atoms.
  • the compound represented by general formula (1) preferably has a structure represented by general formula (2) below.
  • X1 and X2 each independently represent an oxygen atom or a sulfur atom.
  • at least one of X 1 and X 2 is an oxygen atom.
  • at least one of X 1 and X 2 is a sulfur atom.
  • one of X 1 and X 2 is an oxygen atom and the other is a sulfur atom.
  • both X 1 and X 2 are oxygen atoms.
  • both X 1 and X 2 are sulfur atoms.
  • either of the two benzene rings to which X 1 is bonded may be bonded to the benzene ring to which (R 4 ) n4 is bonded.
  • X2 is preferably bonded to the other benzene ring to which it is not bonded.
  • n represents 0 or 1. In one aspect of the invention, n is 0. In one aspect of the invention, n is 1. In general formula (2), n1, n2, n3, n4, n5 and n7 each independently represent an integer of 0-4, and n6 represents an integer of 0-2. In one aspect of the present invention, each of n1-n6 is independently an integer of 0-2. In one aspect of the invention, n1-n6 are each independently 0 or 1. In one aspect of the invention, n1 and n2 are zero. In one aspect of the invention, n3 and n4 are zero. In one aspect of the invention, n5 and n6 are zero.
  • R 1 to R 7 each independently represent a deuterium atom or a substituent.
  • R 1 -R 7 are deuterium atoms.
  • the substituent may be, for example, a substituent selected from the following substituent group A, a substituent selected from the following substituent group B, or a substituent selected from the following substituent group C may be a group, a substituent selected from Substituent Group D below, and a substituent selected from Substituent Group E below.
  • two adjacent R 1 , two adjacent R 2 , two adjacent R 3 , two adjacent R 4 , two adjacent R 5 , two adjacent R 6 and two adjacent R 7 may be bonded to each other to form a cyclic structure.
  • two adjacent R1 's are not bonded to each other and do not form a ring structure.
  • two adjacent R 2 are not bonded to each other and do not form a ring structure.
  • two adjacent R3's are not bonded to each other and do not form a cyclic structure.
  • two adjacent R4 's are not bonded to each other and do not form a ring structure.
  • two adjacent R5's are not bonded to each other and do not form a ring structure.
  • two adjacent R6 are not bonded to each other and do not form a ring structure.
  • two adjacent R7s are not bonded to each other and do not form a ring structure.
  • R 3 and R 4 , two adjacent R 1 , two adjacent R 2 , two adjacent R 3 , two adjacent R 4 , two adjacent None of R 5 , two adjacent R 6 , and two adjacent R 7 are bonded to each other to form a cyclic structure.
  • the compound represented by general formula (1) preferably has a structure represented by any one of the following general formulas (3-1) to (3-16).
  • R 1 to R 7 each independently represent a deuterium atom or a substituent.
  • n represents 0 or 1
  • n1, n2, n3, n4, n5 and n7 each independently represents an integer of 0 to 4
  • n3′ and n4′ each independently represents an integer of 0 to 3 represents an integer
  • n6 represents any integer from 0 to 2.
  • R 3 and R 4 , 2 adjacent R 1 , 2 adjacent R 2 , 2 adjacent R 3 , 2 adjacent R 4 , 2 adjacent R 5 , 2 adjacent R 6 and two adjacent R 7 may combine with each other to form a cyclic structure.
  • One aspect of the present invention has a structure represented by any one of general formulas (3-1) to (3-4).
  • One aspect of the present invention has a structure represented by any one of general formulas (3-5) to (3-8).
  • One aspect of the present invention has a structure represented by any one of general formulas (3-9) to (3-12).
  • One aspect of the present invention has a structure represented by any one of general formulas (3-13) to (3-16).
  • One aspect of the present invention has a structure represented by any one of general formulas (3-1), (3-5), (3-9), and (3-13).
  • One aspect of the present invention has a structure represented by any one of general formulas (3-2), (3-6), (3-10), and (3-14).
  • One aspect of the present invention has a structure represented by any one of general formulas (3-3), (3-7), (3-11), and (3-15).
  • One aspect of the present invention has a structure represented by any one of general formulas (3-4), (3-8), (3-12), and (3-16).
  • general formulas (3-4), (3-8), (3-12), and (3-16 For embodiments and preferred ranges of general formulas (3-1) to (3-16), reference can be made to the corresponding descriptions of general formulas (1) and (2).
  • the compound represented by general formula (1) has only one carbazole structure in the molecule. In one aspect of the present invention, the compound represented by general formula (1) does not have a pyrrole ring that does not form a carbazole structure. In one aspect of the present invention, the compound represented by general formula (1) does not have a furan ring that does not form a dibenzofuran structure. In one aspect of the present invention, the compound represented by general formula (1) does not have a thiophene ring that does not form a dibenzothiophene structure. In one aspect of the present invention, the compound represented by the general formula (1) does not have condensed rings in which six or more rings are condensed.
  • a compound having an asymmetric structure is selected as the compound represented by general formula (1).
  • the molecular weight of the compound represented by the general formula (1) is, for example, 1500 or less when the organic layer containing the compound represented by the general formula (1) is intended to be formed by a vapor deposition method and used. It is preferably 1200 or less, more preferably 1000 or less, and even more preferably 900 or less.
  • the lower limit of the molecular weight is the molecular weight of the smallest compound in the group of compounds represented by general formula (1).
  • the compound represented by general formula (1) may be formed into a film by a coating method regardless of its molecular weight.
  • the compound represented by general formula (1) has the advantage of being easily dissolved in an organic solvent. Therefore, the compound represented by the general formula (1) can be easily applied to the coating method, and can be easily purified to increase its purity.
  • the compound represented by general formula (1) preferably does not contain a metal atom.
  • a compound composed of atoms selected from the group consisting of carbon, hydrogen, deuterium, nitrogen, oxygen and sulfur atoms can be selected.
  • a compound consisting of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms and oxygen atoms can be selected.
  • a compound consisting of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms and oxygen atoms can be selected.
  • a compound composed of atoms selected from the group consisting of carbon atoms, hydrogen atoms, deuterium atoms, nitrogen atoms and sulfur atoms can be selected.
  • a compound consisting of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms and sulfur atoms can be selected.
  • the "alkyl group” may be linear, branched, or cyclic. Moreover, two or more of the linear portion, the cyclic portion and the branched portion may be mixed.
  • the number of carbon atoms in the alkyl group can be, for example, 1 or more, 2 or more, or 4 or more. Also, the number of carbon atoms can be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less.
  • alkyl groups include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, isopentyl group, n-hexyl group, isohexyl group, 2-ethylhexyl group, n-heptyl group, isoheptyl group, n-octyl group, isooctyl group, n-nonyl group, isononyl group, n-decanyl group, isodecanyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group.
  • alkyl group as a substituent may be further substituted with an aryl group.
  • An "alkenyl group” may be linear, branched, or cyclic. Moreover, two or more of the linear portion, the cyclic portion and the branched portion may be mixed.
  • the number of carbon atoms in the alkenyl group can be, for example, 2 or more and 4 or more. Also, the number of carbon atoms can be 30 or less, 20 or less, 10 or less, 6 or less, or 4 or less.
  • alkenyl groups include ethenyl, n-propenyl, isopropenyl, n-butenyl, isobutenyl, n-pentenyl, isopentenyl, n-hexenyl, isohexenyl, and 2-ethylhexenyl groups. can be mentioned.
  • the alkenyl group as a substituent may be further substituted with a substituent.
  • the “aryl group” and “heteroaryl group” may be monocyclic or condensed rings in which two or more rings are condensed. In the case of condensed rings, the number of condensed rings is preferably 2 to 6, and can be selected from 2 to 4, for example.
  • rings include benzene ring, pyridine ring, pyrimidine ring, triazine ring, naphthalene ring, anthracene ring, phenanthrene ring, triphenylene ring, quinoline ring, pyrazine ring, quinoxaline ring, and naphthyridine ring, which are condensed. It may be a circular ring.
  • aryl or heteroaryl groups include phenyl, 1-naphthyl, 2-naphthyl, 1-anthracenyl, 2-anthracenyl, 9-anthracenyl, 2-pyridyl, 3-pyridyl, 4 - pyridyl group.
  • the number of atoms constituting the ring skeleton of the aryl group is preferably 6 to 40, more preferably 6 to 20, selected within the range of 6 to 14, or selected within the range of 6 to 10.
  • the number of atoms constituting the ring skeleton of the heteroaryl group is preferably 4 to 40, more preferably 5 to 20, selected within the range of 5 to 14, or selected within the range of 5 to 10. You may "Arylene group” and "heteroaryl group” can be read by changing the valence number from 1 to 2 in the description of the aryl group and heteroaryl group.
  • substituted group A refers to a hydroxyl group, a halogen atom (e.g., fluorine atom, chlorine atom, bromine atom, iodine atom), an alkyl group (e.g., 1 to 40 carbon atoms), an alkoxy group (e.g., 1 to 40), alkylthio groups (eg, 1 to 40 carbon atoms), aryl groups (eg, 6 to 30 carbon atoms), aryloxy groups (eg, 6 to 30 carbon atoms), arylthio groups (eg, 6 to 30 carbon atoms), Heteroaryl group (eg, 5 to 30 ring atoms), heteroaryloxy group (eg, 5 to 30 ring atoms), heteroarylthio group (eg, 5 to 30 ring atoms), acyl group ( For example, 1 to 40 carbon atoms), alkenyl groups (eg, 1 to 40 carbon atoms), alkenyl groups (eg, 1 to 40
  • substituted group B means an alkyl group (eg, 1 to 40 carbon atoms), an alkoxy group (eg, 1 to 40 carbon atoms), an aryl group (eg, 6 to 30 carbon atoms), an aryloxy group (eg for example, 6 to 30 carbon atoms), heteroaryl groups (eg, 5 to 30 ring atoms), heteroaryloxy groups (eg, 5 to 30 ring atoms), diarylaminoamino groups (eg, 0 to 30 carbon atoms).
  • substituted group C refers to an alkyl group (eg, 1 to 20 carbon atoms), an aryl group (eg, 6 to 22 carbon atoms), a heteroaryl group (eg, 5 to 20 ring skeleton atoms), It means one group or a combination of two or more groups selected from the group consisting of diarylamino groups (eg, 12 to 20 carbon atoms).
  • substituted group D refers to an alkyl group (eg, 1 to 20 carbon atoms), an aryl group (eg, 6 to 22 carbon atoms) and a heteroaryl group (eg, 5 to 20 ring skeleton atoms). It means one group selected from the group consisting of or a combination of two or more groups.
  • substituted group E refers to one group selected from the group consisting of an alkyl group (eg, 1 to 20 carbon atoms) and an aryl group (eg, 6 to 22 carbon atoms), or a combination of two or more means a group.
  • substituent when described as “substituent” or “substituted or unsubstituted” may be selected from, for example, substituent group A, or selected from substituent group B. may be selected from Substituent Group C, may be selected from Substituent Group D, or may be selected from Substituent Group E.
  • the compound represented by the general formula (1) can be synthesized by appropriately combining known synthesis methods. For example, by reacting DH with XAr-Z, it is possible to synthesize D-Ar-Z of general formula (1).
  • H is a hydrogen atom
  • X is a halogen atom (eg fluorine, chlorine, bromine or iodine). Reaction conditions can be optimized by techniques well known to those skilled in the art.
  • the compound represented by the general formula (1) may be used as a host material for a light-emitting material (dopant), or may be used as a charge transport material or a light-emitting material depending on the mode of use. When used as a host material for a light-emitting material, it may be used as a host material for any of a delayed fluorescent material, a fluorescent material that does not emit delayed fluorescence (immediate fluorescent material), or a phosphorescent material.
  • the compound represented by general formula (1) is particularly excellent as a host material for light-emitting materials.
  • the compound represented by general formula (1) is particularly useful as a host material for use with a delayed fluorescence material.
  • delayed fluorescence material means that in an excited state, reverse intersystem crossing occurs from an excited triplet state to an excited singlet state, and delayed fluorescence is emitted when returning from the excited singlet state to the ground state. It is an organic compound.
  • a delayed fluorescence material is defined as a material that emits fluorescence with an emission lifetime of 100 ns (nanoseconds) or more when measured by a fluorescence lifetime measurement system (such as a streak camera system manufactured by Hamamatsu Photonics).
  • the delayed fluorescence material receives energy from the compound represented by the general formula (1) in an excited singlet state to an excited singlet state transition to Further, the delayed fluorescence material may receive energy from the compound represented by general formula (1) in the excited triplet state and transition to the excited triplet state. Since the delayed fluorescent material has a small difference ( ⁇ EST ) between the excited singlet energy and the excited triplet energy, the delayed fluorescent material in the excited triplet state easily undergoes reverse intersystem crossing to the delayed fluorescent material in the excited singlet state. The delayed fluorescent material in the excited singlet state generated by these pathways contributes to light emission.
  • the difference ⁇ EST between the lowest excited singlet energy and the lowest excited triplet energy at 77K is preferably 0.3 eV or less, more preferably 0.25 eV or less, and 0.2 eV or less. is more preferably 0.15 eV or less, more preferably 0.1 eV or less, even more preferably 0.07 eV or less, and even more preferably 0.05 eV or less , is more preferably 0.03 eV or less, and particularly preferably 0.01 eV or less.
  • ⁇ EST is small, reverse intersystem crossing from the excited singlet state to the excited triplet state is likely to occur due to the absorption of thermal energy, and thus the material functions as a thermally activated delayed fluorescence material.
  • a thermally activated delayed fluorescence material absorbs the heat emitted by the device and undergoes reverse intersystem crossing from the excited triplet state to the excited singlet relatively easily, and the excited triplet energy efficiently contributes to light emission. can be done.
  • the lowest excited singlet energy (E S1 ) and the lowest excited triplet energy (E T1 ) of the compound in the present invention are values determined by the following procedure.
  • ⁇ E ST is a value obtained by calculating E S1 -E T1 .
  • (2) Lowest excited singlet energy (E S1 ) A thin film or a toluene solution (concentration 10 ⁇ 5 mol/L) of the compound to be measured is prepared and used as a sample. The fluorescence spectrum of this sample is measured at room temperature (300K). In the fluorescence spectrum, the vertical axis is light emission and the horizontal axis is wavelength.
  • the maximum point with a peak intensity of 10% or less of the maximum peak intensity of the spectrum is not included in the maximum value on the shortest wavelength side described above, and is closest to the maximum value on the short wavelength side.
  • the tangent line drawn at the point where the value is taken is taken as the tangent line to the rise on the short wavelength side of the phosphorescence spectrum.
  • a compound (cyanobenzene derivative) having a cyanobenzene structure in which the benzene ring is substituted with one cyano group is used as the delayed fluorescence material.
  • a compound (dicyanobenzene derivative) having a dicyanobenzene structure in which two cyano groups are substituted on the benzene ring is used as the delayed fluorescence material.
  • a compound (azabenzene derivative) having an azabenzene structure in which at least one carbon atom constituting the ring skeleton of a benzene ring is substituted with a nitrogen atom is used as the delayed fluorescence material.
  • a compound represented by the following general formula (4) is used as the delayed fluorescence material.
  • one of R 21 to R 23 represents a cyano group or a group represented by general formula (5) below, and the remaining two of R 21 to R 23 and R 24 and R 25 At least one of them represents a group represented by the following general formula (6), and the rest of R 21 to R 25 are hydrogen atoms or substituents (wherein the substituent here is a cyano group, the following general formula (5) is not a group represented by the following general formula (6)).
  • L 1 represents a single bond or a divalent linking group
  • R 31 and R 32 each independently represent a hydrogen atom or a substituent
  • * represents a bonding position
  • L2 represents a single bond or a divalent linking group
  • R33 and R34 each independently represent a hydrogen atom or a substituent
  • * represents a bonding position
  • R 22 is a cyano group. In a preferred embodiment of the present invention, R 22 is a group represented by general formula (5). In one aspect of the present invention, R 21 is a cyano group or a group represented by general formula (5). In one aspect of the present invention, R 23 is a cyano group or a group represented by general formula (5). In one aspect of the invention, one of R 21 to R 23 is a cyano group. In one aspect of the present invention, one of R 21 to R 23 is a group represented by general formula (5).
  • L 1 in general formula (5) is a single bond.
  • L 1 is a divalent linking group, preferably a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group, more preferably a substituted or unsubstituted arylene group and more preferably a substituted or unsubstituted 1,4-phenylene group (for example, an alkyl group having 1 to 3 carbon atoms as a substituent).
  • R 31 and R 32 in general formula (5) are each independently an alkyl group (eg, 1 to 40 carbon atoms), an aryl group (eg, 6 to 30 carbon atoms), a heteroaryl group (eg, one group selected from the group consisting of 5 to 30 ring skeleton atoms), an alkenyl group (for example, 1 to 40 carbon atoms) and an alkynyl group (for example, 1 to 40 carbon atoms), or a combination of two or more (these groups are hereinafter referred to as "substituent group A groups").
  • alkyl group eg, 1 to 40 carbon atoms
  • aryl group eg, 6 to 30 carbon atoms
  • a heteroaryl group eg, one group selected from the group consisting of 5 to 30 ring skeleton atoms
  • an alkenyl group for example, 1 to 40 carbon atoms
  • an alkynyl group for example, 1 to 40 carbon atoms
  • each of R 31 and R 32 is independently a substituted or unsubstituted aryl group (eg, having 6 to 30 carbon atoms), and the substituent of the aryl group is a group of substituent group A. can be mentioned.
  • R 31 and R 32 are the same.
  • L2 in general formula ( 6 ) is a single bond.
  • L2 is a divalent linking group, preferably a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group, more preferably a substituted or unsubstituted arylene group and more preferably a substituted or unsubstituted 1,4-phenylene group (for example, an alkyl group having 1 to 3 carbon atoms as a substituent).
  • R 33 and R 34 in general formula (6) are each independently a substituted or unsubstituted alkyl group (eg, 1 to 40 carbon atoms), a substituted or unsubstituted alkenyl group (eg, 1 to 40), a substituted or unsubstituted aryl group (eg, 6 to 30 carbon atoms), or a substituted or unsubstituted heteroaryl group (eg, 5 to 30 carbon atoms).
  • substituents of the alkyl group, alkenyl group, aryl group, and heteroaryl group referred to herein include hydroxyl group, halogen atom (eg, fluorine atom, chlorine atom, bromine atom, iodine atom), alkyl group (eg, C 1-40 ), an alkoxy group (eg, 1 to 40 carbon atoms), an alkylthio group (eg, 1 to 40 carbon atoms), an aryl group (eg, 6 to 30 carbon atoms), an aryloxy group (eg, 6 to 30 carbon atoms), an arylthio group ( (e.g., 6 to 30 carbon atoms), heteroaryl groups (e.g., 5 to 30 ring atoms), heteroaryloxy groups (e.g., 5 to 30 ring atoms), heteroarylthio groups (e.g., ring atoms) 5 to 30), acyl groups (eg, 1 to 40 carbon atoms), alky
  • R 33 and R 34 may be bonded to each other via a single bond or a linking group to form a cyclic structure.
  • R 33 and R 34 are aryl groups, they are preferably bonded to each other via a single bond or a linking group to form a cyclic structure.
  • R 35 to R 37 each independently represent a hydrogen atom or a substituent.
  • a group of the above substituent group A can be selected, or a group of the following substituent group B can be selected, preferably an alkyl group having 1 to 10 carbon atoms and an alkyl group having 6 to 14 carbon atoms. It is one group or a combination of two or more groups selected from the group consisting of aryl groups.
  • the group represented by general formula (6) is preferably a group represented by general formula (7) below.
  • L11 in general formula ( 7 ) represents a single bond or a divalent linking group.
  • the description and preferred range of L 11 can be referred to the description and preferred range of L 2 above.
  • Each of R 41 to R 48 in general formula (7) independently represents a hydrogen atom or a substituent.
  • R 41 and R 42 , R 42 and R 43 , R 43 and R 44 , R 44 and R 45 , R 45 and R 46 , R 46 and R 47 , R 47 and R 48 are bonded to each other to form a cyclic structure. may be formed.
  • the cyclic structure formed by bonding to each other may be an aromatic ring or an alicyclic ring, or may contain a heteroatom, and the cyclic structure may be a condensed ring of two or more rings.
  • the heteroatoms referred to here are preferably those selected from the group consisting of nitrogen atoms, oxygen atoms and sulfur atoms.
  • Examples of cyclic structures formed include benzene ring, naphthalene ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, pyrrole ring, imidazole ring, pyrazole ring, imidazoline ring, oxazole ring, isoxazole ring, thiazole ring, iso thiazole ring, cyclohexadiene ring, cyclohexene ring, cyclopentaene ring, cycloheptatriene ring, cycloheptadiene ring, cycloheptaene ring, furan ring, thiophene ring, naphthyridine ring, quinoxaline ring, quinoline ring and the like.
  • a ring formed by condensing a large number of rings such as a phenanthrene ring or a triphenylene ring may be formed.
  • the number of rings contained in the group represented by general formula (7) may be selected from the range of 3-5, or may be selected from the range of 5-7.
  • substituents that R 41 to R 48 can take include the groups of the above substituent group B, preferably unsubstituted alkyl groups having 1 to 10 carbon atoms or unsubstituted alkyl groups having 1 to 10 carbon atoms. It is an aryl group having 6 to 10 carbon atoms which may be substituted with an alkyl group.
  • R 41 to R 48 are hydrogen atoms or unsubstituted alkyl groups having 1 to 10 carbon atoms. In a preferred embodiment of the present invention, R 41 to R 48 are hydrogen atoms or unsubstituted aryl groups having 6 to 10 carbon atoms. In a preferred embodiment of the present invention, all of R 41 to R 48 are hydrogen atoms.
  • * represents a bonding position.
  • a preferred embodiment of the present invention uses an azabenzene derivative as the delayed fluorescence material.
  • the azabenzene derivative has an azabenzene structure in which three of the ring skeleton-constituting carbon atoms of the benzene ring are substituted with nitrogen atoms.
  • an azabenzene derivative having a 1,3,5-triazine structure can be preferably selected.
  • the azabenzene derivative has an azabenzene structure in which two of the ring skeleton-constituting carbon atoms of the benzene ring are substituted with nitrogen atoms.
  • azabenzene derivatives having a pyridazine structure, a pyrimidine structure, and a pyrazine structure can be mentioned, and azabenzene derivatives having a pyrimidine structure can be preferably selected.
  • the azabenzene derivative has a pyridine structure in which one of the ring skeleton-constituting carbon atoms of the benzene ring is substituted with a nitrogen atom.
  • a compound represented by the following general formula (8) is used as the delayed fluorescence material.
  • at least one of Y 1 , Y 2 and Y 3 represents a nitrogen atom and the rest represent methine groups.
  • Y 1 is a nitrogen atom and Y 2 and Y 3 are methine groups.
  • Y 1 and Y 2 are preferably nitrogen atoms and Y 3 is preferably a methine group. More preferably, all of Y 1 to Y 3 are nitrogen atoms.
  • Z 1 to Z 3 each independently represent a hydrogen atom or a substituent, at least one of which is a donor substituent.
  • a donor substituent means a group having a negative Hammett's ⁇ p value.
  • at least one of Z 1 to Z 3 is a group containing a diarylamino structure (two aryl groups bonded to the nitrogen atom may be bonded to each other), more preferably the general formula (6 ), for example, a group represented by the general formula (7).
  • only one of Z 1 to Z 3 is a group represented by general formula (6) or (7).
  • only two of Z 1 to Z 3 are each independently a group represented by general formula (6) or (7).
  • all of Z 1 to Z 3 are each independently a group represented by general formula (6) or (7).
  • Z 1 to Z 3 that are not groups represented by general formulas (6) and (7) are substituted or unsubstituted aryl groups (eg, 6 to 40 carbon atoms, preferably 6 to 20 carbon atoms).
  • the substituents of the aryl group referred to herein include an aryl group (eg, 6 to 20 carbon atoms, preferably 6 to 14 carbon atoms) and an alkyl group (eg, 1 to 20 carbon atoms, preferably 1 to 6).
  • aryl group eg, 6 to 20 carbon atoms, preferably 6 to 14 carbon atoms
  • alkyl group eg, 1 to 20 carbon atoms, preferably 1 to 6
  • general formula (8) does not contain a cyano group.
  • a compound represented by the following general formula (9) is used as the delayed fluorescence material.
  • Ar 1 forms a cyclic structure that may be substituted with A 1 and D 1 below, and represents a benzene ring, naphthalene ring, anthracene ring, or phenanthrene ring.
  • Ar 2 and Ar 3 each may form a cyclic structure, and when they form a cyclic structure, they represent a benzene ring, a naphthalene ring, a pyridine ring, or a cyano-substituted benzene ring.
  • D 1 represents a substituted or unsubstituted 5H-indolo[3,2,1-de]phenazin-5-yl group or a substituted or unsubstituted heterocyclic condensed carbazolyl group containing no naphthalene structure; ), they may be the same or different. Also, the substituents of D 1 may be bonded to each other to form a cyclic structure.
  • delayed fluorescence material Preferred compounds that can be used as the delayed fluorescence material are listed below, but the delayed fluorescence material that can be used in the present invention is not limited to these specific examples.
  • known delayed fluorescence materials other than those described above can be used in appropriate combination with the compound represented by general formula (1). Moreover, even unknown delayed fluorescence materials can be used.
  • the delayed fluorescence material paragraphs 0008 to 0048 and 0095 to 0133 of WO2013/154064, paragraphs 0007 to 0047 and 0073 to 0085 of WO2013/011954, paragraphs 0007 to 0033 and 0059 to 0066 of WO2013/011955, Paragraphs 0008 to 0071 and 0118 to 0133 of WO2013/081088, paragraphs 0009 to 0046 and 0093 to 0134 of JP 2013-256490, paragraphs 0008 to 0020 and 0038 to 0040 of JP 2013-116975, WO2013 / Paragraphs 0007 to 0032 and 0079 to 0084 of 133359, paragraphs 0008 to 0054 and 0101 to 0121 of WO2013/161437, paragraphs 0007 to 0041 and 0060
  • JP 2013-253121, WO2013/133359, WO2014/034535, WO2014/115743, WO2014/122895, WO2014/126200, WO2014/136758, WO2014/133121 Publications, WO2014/136860, WO2014/196585, WO2014/189122, WO2014/168101, WO2015/008580, WO2014/203840, WO2015/002213, WO2010/01620 WO2015/019725, WO2015/072470, WO2015/108049, WO2015/080182, WO2015/072537, WO2015/080183, JP 2015-129240, WO2015/129714, WO2015/129715, WO2015/133501, WO2015/136880, WO2015/137244, WO2015/137202, WO2015/137136, WO2015/146541, WO2015/159541
  • a luminescent material that emits delayed fluorescence can also be employed.
  • the delayed fluorescence material used in the present invention preferably does not contain metal atoms.
  • a compound composed of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, oxygen atoms and sulfur atoms can be selected.
  • a compound composed of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms and oxygen atoms can be selected.
  • a compound composed of carbon atoms, hydrogen atoms and nitrogen atoms can be selected as the delayed fluorescence material.
  • composition contains a compound represented by formula (1) and a delayed fluorescence material.
  • the composition is composed only of one or more compounds represented by general formula (1) and one or more delayed fluorescence materials.
  • the composition comprises only one type of compound represented by general formula (1) and one type of delayed fluorescence material.
  • the composition contains a third component in addition to the compound represented by formula (1) and the delayed fluorescence material.
  • the third component here is neither the compound represented by the general formula (1) nor the delayed fluorescence material. Only one type of the third component may be contained, or two or more types may be contained.
  • the content of the third component in the composition may be selected within the range of 30% by weight or less, may be selected within the range of 10% by weight or less, or may be selected within the range of 1% by weight or less. It may be selected, or may be selected within the range of 0.1% by weight or less.
  • the third component does not emit light.
  • the third component emits fluorescence.
  • the largest component of luminescence from the composition of the present invention is fluorescence (including delayed fluorescence).
  • the content of the compound represented by general formula (1) is greater than that of the delayed fluorescence material on a weight basis.
  • the content of the compound represented by the general formula (1) may be selected within a range of 3 times or more by weight the content of the delayed fluorescence material, or may be selected within a range of 10 times or more by weight. However, it may be selected within a range of 100 times by weight or more, may be selected within a range of 1000 times by weight or more, or may be selected within a range of, for example, 10000 times by weight or less. In the composition of the present invention, it is preferable to select a delayed fluorescence material having an excited singlet energy smaller than the excited singlet energy of the compound represented by formula (1).
  • the difference in excited singlet energy may be 0.1 eV or more, 0.3 eV or more, or 0.5 eV or more, and may be 2 eV or less, 1.5 eV or less, or 1.0 eV or less.
  • the composition of the present invention preferably does not contain metal elements.
  • the composition of the invention consists exclusively of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, oxygen atoms, sulfur atoms, boron atoms and halogen atoms.
  • the composition of the invention consists exclusively of atoms selected from the group consisting of carbon atoms, hydrogen atoms, nitrogen atoms, oxygen atoms and sulfur atoms.
  • the compound represented by general formula (1) is useful as a host material for use with a delayed fluorescence material and a fluorescent compound. Therefore, in one aspect of the present invention, the composition of the present invention contains a fluorescent compound in addition to the compound represented by formula (1) and the delayed fluorescent material.
  • the fluorescent compound preferably has a lower lowest excited singlet energy (E S1 ) than the compound represented by formula (1) and the delayed fluorescent material.
  • the fluorescent compound absorbs energy from the compound represented by general formula (1) in the excited singlet state, the delayed fluorescent material, and the delayed fluorescent material in the excited singlet state through inverse intersystem crossing from the excited triplet state. It receives and transitions to a singlet excited state, and then emits fluorescence when returning to the ground state.
  • the fluorescent compound is not particularly limited as long as it can receive energy from the compound represented by the general formula (1) and the delayed fluorescence material and emit fluorescence. It may be delayed fluorescence.
  • the luminescent material used as the fluorescent compound preferably emits fluorescence when returning from the lowest excited singlet energy level to the ground energy level.
  • Fluorescent compounds include anthracene derivatives, tetracene derivatives, naphthacene derivatives, pyrene derivatives, perylene derivatives, chrysene derivatives, rubrene derivatives, coumarin derivatives, pyran derivatives, stilbene derivatives, fluorene derivatives, anthryl derivatives, pyrromethene derivatives, terphenyl derivatives, terphenyl derivatives, Phenylene derivatives, fluoranthene derivatives, amine derivatives, quinacridone derivatives, oxadiazole derivatives, malononitrile derivatives, pyran derivatives, carbazole derivatives, julolidine derivatives, thiazole derivatives, derivatives containing metals (Al, Zn), diazaboranaphthoanthracene, etc.
  • the fluorescent compound include the compounds given as specific examples of the delayed fluorescence material.
  • the composition of the present invention contains two or more delayed fluorescence materials, and the one with the higher lowest singlet excited energy functions as an assist dopant, and the one with the lower lowest singlet excited energy functions as a fluorescent compound that mainly emits light.
  • the compound used as the fluorescent compound preferably exhibits a PL emission quantum yield of 60% or more, more preferably 80% or more.
  • the compound used as the fluorescent compound preferably exhibits an instantaneous fluorescence lifetime of 50 ns or less, more preferably 20 ns or less.
  • the instantaneous fluorescence lifetime at this time is the luminescence lifetime of the fastest decaying component among multiple exponentially decaying components observed when luminescence lifetime measurement is performed for a compound exhibiting thermally activated delayed fluorescence.
  • the compound used as the third compound preferably has a fluorescence emission rate from the lowest excited singlet (S1) to the ground state higher than an intersystem crossing rate from S1 to the lowest excited triplet (T1).
  • S1 lowest excited singlet
  • T1 intersystem crossing rate from S1 to the lowest excited triplet
  • the rate constant of the compound refer to known literature on thermally activated delayed fluorescence materials (H. Uoyama, et al., Nature 492, 234 (2012) and K. Masui, et al., Org. Electron. 14 , 2721, (2013), etc.).
  • Preferred compounds that can be used as fluorescent compounds that are used together with the delayed fluorescent material are listed below, but the fluorescent compounds that can be used in the present invention are not limited to these specific examples.
  • the compound represented by General Formula (1) can be used together with another host material for a light-emitting layer (composition) containing a plurality of host materials. That is, in one aspect of the present invention, the composition of the present invention contains multiple host materials containing the compound represented by general formula (1). In the composition of the present invention, a plurality of types of compounds represented by general formula (1) may be used, or a compound represented by general formula (1) and a host material not represented by general formula (1) may be used. They may be used in combination. Preferred compounds that can be used as the second host material together with the compound represented by the general formula (1) are listed below. It should not be interpreted restrictively.
  • the form of the composition of the present invention is not particularly limited.
  • the composition of the invention is in the form of a film.
  • a film comprising the composition of the present invention may be formed by a wet process or a dry process.
  • a solution in which the composition of the present invention is dissolved is applied to the surface, and the luminescent layer is formed after removing the solvent.
  • wet processes include spin coating, slit coating, ink jet (spray), gravure printing, offset printing, and flexographic printing, but are not limited to these.
  • a suitable organic solvent is selected and used that is capable of dissolving the composition of the present invention.
  • compounds included in the compositions of the present invention can be introduced with substituents (eg, alkyl groups) that increase their solubility in organic solvents.
  • a vacuum vapor deposition method can be preferably employed as the dry process. When a vacuum deposition method is employed, each compound constituting the composition of the present invention may be co-deposited from individual deposition sources, or all the compounds may be co-deposited from a single deposition source mixed. . When a single vapor deposition source is used, a mixed powder obtained by mixing powders of all the compounds may be used, a compression molding obtained by compressing the mixed powder may be used, or each compound may be heated and melted and mixed. A mixture that has been cooled after heating may be used.
  • the composition ratio of the plurality of compounds contained in the vapor deposition source is reduced by co-deposition under conditions in which the vapor deposition rates (weight reduction rates) of the plurality of compounds contained in the single vapor deposition source match or substantially match. It is possible to form a film having a composition ratio corresponding to A film having a desired composition ratio can be easily formed by mixing a plurality of compounds at the same composition ratio as that of the film to be formed, and using this as an evaporation source. In one embodiment, the temperature at which each of the co-deposited compounds has the same weight loss rate can be identified and used as the temperature during co-deposition.
  • the molecular weight of each compound constituting the composition is preferably 1500 or less, more preferably 1200 or less, further preferably 1000 or less, and 900 or less. It is even more preferred to have The lower limit of the molecular weight may be 450, 500, or 600, for example.
  • Organic light-emitting element Excellent organic light-emitting devices such as organic photoluminescence devices (organic PL devices) and organic electroluminescence devices (organic EL devices) can be provided by forming a light-emitting layer comprising the composition of the present invention.
  • the organic light-emitting device of the present invention is a fluorescent light-emitting device, and the largest component of light emitted from the device is fluorescence (the fluorescence referred to herein includes delayed fluorescence).
  • the thickness of the light-emitting layer can be, for example, 1-15 nm, 2-10 nm, or 3-7 nm.
  • An organic photoluminescence device has a structure in which at least a light-emitting layer is formed on a substrate.
  • the organic electroluminescence element has a structure in which at least an anode, a cathode, and an organic layer are formed between the anode and the cathode.
  • the organic layer includes at least a light-emitting layer, and may consist of only the light-emitting layer, or may have one or more organic layers in addition to the light-emitting layer.
  • Such other organic layers can include hole transport layers, hole injection layers, electron blocking layers, hole blocking layers, electron injection layers, electron transport layers, exciton blocking layers, and the like.
  • the hole transport layer may be a hole injection transport layer having a hole injection function
  • the electron transport layer may be an electron injection transport layer having an electron injection function.
  • the organic light-emitting device of the present invention is a multi-wavelength light-emitting organic light-emitting device
  • the emission with the shortest wavelength may include delayed fluorescence.
  • it is also possible that the emission with the shortest wavelength does not contain delayed fluorescence.
  • An organic light-emitting device using the composition of the present invention when excited by thermal or electronic means, has a blue, green, yellow, orange, and red region (for example, 420-500 nm, 500 nm) in the ultraviolet region and the visible spectrum.
  • organic light emitting devices can emit light in the red or orange region (eg, 620-780 nm).
  • organic light emitting devices can emit light in the orange or yellow region (eg, 570-620 nm).
  • an organic light emitting device can emit light in the green region (eg, 490-575 nm).
  • an organic light emitting device can emit light in the blue region (eg, 400-490 nm).
  • organic light emitting devices can emit light in the ultraviolet spectral region (eg, 280-400 nm).
  • organic light emitting devices can emit light in the infrared spectral region (eg, 780 nm to 2 ⁇ m). It is preferable that the largest component of light emission from the organic light-emitting device using the composition of the present invention is light emission from the delayed fluorescence material contained in the composition of the present invention.
  • Emission from the compound represented by the general formula (1) is preferably less than 10% of the light emission from the organic light-emitting device, for example, less than 1%, less than 0.1%, less than 0.01%, detection limit It may be below.
  • Emission from the delayed fluorescence material may be, for example, more than 50%, more than 90%, more than 99% of the emission from the organic light emitting device.
  • the layer containing the composition of the present invention contains a fluorescent material as the third component
  • the maximum component of light emitted from the organic light-emitting device may be light emitted from the fluorescent material.
  • the emission from the luminescent material may be, for example, more than 50%, more than 90%, more than 99% of the emission from the organic light emitting device.
  • the organic electroluminescent device of the present invention is held by a substrate, which is not particularly limited and commonly used in organic electroluminescent devices such as glass, transparent plastic, quartz and silicon. Any material formed by
  • the anode of the organic electroluminescent device is made from metals, alloys, conductive compounds, or combinations thereof.
  • the metal, alloy or conductive compound has a high work function (4 eV or greater).
  • the metal is Au.
  • the conductive transparent material is selected from CuI, indium tin oxide ( ITO), SnO2 and ZnO. Some embodiments use amorphous materials that can form transparent conductive films, such as IDIXO (In 2 O 3 —ZnO).
  • the anode is a thin film. In some embodiments, the thin film is made by evaporation or sputtering.
  • the film is patterned by photolithographic methods. In some embodiments, if the pattern does not need to be highly precise (eg, about 100 ⁇ m or greater), the pattern may be formed using a mask with a shape suitable for vapor deposition or sputtering onto the electrode material. In some embodiments, wet film forming methods such as printing and coating methods are used when coating materials such as organic conductive compounds can be applied.
  • the anode has a transmittance of greater than 10% when emitted light passes through the anode, and the anode has a sheet resistance of several hundred ohms per unit area or less. In some embodiments, the thickness of the anode is 10-1,000 nm. In some embodiments, the thickness of the anode is 10-200 nm. In some embodiments, the thickness of the anode varies depending on the material used.
  • the cathode is made of electrode materials such as metals with a low work function (4 eV or less) (referred to as electron-injecting metals), alloys, conductive compounds, or combinations thereof.
  • the electrode material is sodium, sodium-potassium alloys, magnesium, lithium, magnesium-copper mixtures, magnesium-silver mixtures, magnesium-aluminum mixtures, magnesium-indium mixtures, aluminum - aluminum oxide (Al2 O 3 ) mixtures, indium, lithium-aluminum mixtures and rare earth elements.
  • a mixture of an electron-injecting metal and a second metal that is a stable metal with a higher work function than the electron-injecting metal is used.
  • the mixture is selected from magnesium-silver mixtures, magnesium-aluminum mixtures, magnesium-indium mixtures, aluminum-aluminum oxide (Al 2 O 3 ) mixtures, lithium-aluminum mixtures and aluminum. In some embodiments, the mixture improves electron injection properties and resistance to oxidation.
  • the cathode is manufactured by depositing or sputtering the electrode material as a thin film. In some embodiments, the cathode has a sheet resistance of no more than several hundred ohms per unit area. In some embodiments, the thickness of said cathode is between 10 nm and 5 ⁇ m. In some embodiments, the thickness of the cathode is 50-200 nm.
  • either one of the anode and cathode of the organic electroluminescent device is transparent or translucent to allow transmission of emitted light.
  • transparent or translucent electroluminescent elements enhance light radiance.
  • the cathode is formed of a conductive transparent material as described above for the anode, thereby forming a transparent or translucent cathode.
  • the device includes an anode and a cathode, both transparent or translucent.
  • the injection layer is the layer between the electrode and the organic layer. In some embodiments, the injection layer reduces drive voltage and enhances light radiance. In some embodiments, the injection layer comprises a hole injection layer and an electron injection layer. The injection layer can be placed between the anode and the light-emitting layer or hole-transporting layer and between the cathode and the light-emitting layer or electron-transporting layer. In some embodiments, an injection layer is present. In some embodiments, there is no injection layer. Preferred examples of compounds that can be used as the hole injection material are given below.
  • a barrier layer is a layer that can prevent charges (electrons or holes) and/or excitons present in the light-emitting layer from diffusing out of the light-emitting layer.
  • an electron blocking layer is between the light-emitting layer and the hole-transporting layer to block electrons from passing through the light-emitting layer to the hole-transporting layer.
  • a hole blocking layer is between the emissive layer and the electron transport layer and blocks holes from passing through the emissive layer to the electron transport layer.
  • the barrier layer prevents excitons from diffusing out of the emissive layer.
  • the electron blocking layer and the hole blocking layer constitute an exciton blocking layer.
  • the terms "electron blocking layer” or “exciton blocking layer” include layers that have both the functionality of an electron blocking layer and an exciton blocking layer.
  • Hole blocking layer functions as an electron transport layer. In some embodiments, the hole blocking layer blocks holes from reaching the electron transport layer during electron transport. In some embodiments, the hole blocking layer increases the probability of recombination of electrons and holes in the emissive layer.
  • the materials used for the hole blocking layer can be the same materials as described above for the electron transport layer. Preferred examples of compounds that can be used in the hole blocking layer are given below.
  • Electron barrier layer The electron blocking layer transports holes. In some embodiments, the electron blocking layer prevents electrons from reaching the hole transport layer during hole transport. In some embodiments, the electron blocking layer increases the probability of recombination of electrons and holes in the emissive layer.
  • the materials used for the electron blocking layer may be the same materials as described above for the hole transport layer. Specific examples of preferred compounds that can be used as the electron barrier material are given below.
  • Exciton barrier layer The exciton blocking layer prevents excitons generated through recombination of holes and electrons in the light emitting layer from diffusing to the charge transport layer. In some embodiments, the exciton blocking layer allows effective confinement of excitons in the emissive layer. In some embodiments, the light emission efficiency of the device is improved. In some embodiments, the exciton blocking layer is adjacent to the emissive layer on either the anode side or the cathode side, and on both sides thereof. In some embodiments, when an exciton blocking layer is present on the anode side, it may be present between and adjacent to the hole-transporting layer and the light-emitting layer.
  • an exciton blocking layer when an exciton blocking layer is present on the cathode side, it may be between and adjacent to the emissive layer and the cathode. In some embodiments, a hole-injection layer, electron-blocking layer, or similar layer is present between the anode and an exciton-blocking layer adjacent to the light-emitting layer on the anode side. In some embodiments, a hole injection layer, electron blocking layer, hole blocking layer, or similar layer is present between the cathode and an exciton blocking layer adjacent to the emissive layer on the cathode side. In some embodiments, the exciton blocking layer comprises an excited singlet energy and an excited triplet energy, at least one of which is higher than the excited singlet energy and triplet energy, respectively, of the emissive material.
  • the hole-transporting layer comprises a hole-transporting material.
  • the hole transport layer is a single layer.
  • the hole transport layer has multiple layers.
  • the hole transport material has one property of a hole injection or transport property and an electron barrier property.
  • the hole transport material is an organic material.
  • the hole transport material is an inorganic material. Examples of known hole transport materials that can be used in the present invention include, but are not limited to, triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolones.
  • the hole transport material is selected from porphyrin compounds, aromatic tertiary amine compounds and styrylamine compounds. In some embodiments, the hole transport material is an aromatic tertiary amine compound. Specific examples of preferred compounds that can be used as the hole-transporting material are given below.
  • the electron transport layer includes an electron transport material.
  • the electron transport layer is a single layer.
  • the electron transport layer has multiple layers.
  • the electron-transporting material need only function to transport electrons injected from the cathode to the emissive layer.
  • the electron transport material also functions as a hole blocking material.
  • electron-transporting layers examples include, but are not limited to, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, carbodiimides, fluorenylidene methane derivatives, anthraquinodimethanes, anthrone derivatives, oxazide Azole derivatives, azole derivatives, azine derivatives or combinations thereof, or polymers thereof.
  • the electron transport material is a thiadiazole derivative or a quinoxaline derivative.
  • the electron transport material is a polymeric material. Specific examples of preferred compounds that can be used as the electron-transporting material are given below.
  • examples of preferred compounds as materials that can be added to each organic layer are given.
  • it may be added as a stabilizing material.
  • Preferred materials that can be used in organic electroluminescence elements are specifically exemplified, but materials that can be used in the present invention are not limitedly interpreted by the following exemplified compounds. Moreover, even compounds exemplified as materials having specific functions can be used as materials having other functions.
  • the emissive layer is incorporated into the device.
  • devices include, but are not limited to, OLED bulbs, OLED lamps, television displays, computer monitors, mobile phones and tablets.
  • an electronic device includes an OLED having at least one organic layer including an anode, a cathode, and a light-emitting layer between the anode and the cathode.
  • compositions described herein can be incorporated into various photosensitive or photoactivated devices, such as OLEDs or optoelectronic devices.
  • the composition may be useful in facilitating charge or energy transfer within a device and/or as a hole transport material.
  • OLEDs organic light emitting diodes
  • OICs organic integrated circuits
  • O-FETs organic field effect transistors
  • O-TFTs organic thin film transistors
  • O-LETs organic light emitting transistors
  • O-SC organic solar cells.
  • O-SC organic optical detectors
  • O-FQD organic field-quench devices
  • LOC luminescent fuel cells
  • O-lasers organic laser diodes
  • an electronic device includes an OLED including at least one organic layer including an anode, a cathode, and a light-emitting layer between the anode and the cathode.
  • the device includes OLEDs of different colors.
  • the device includes an array including combinations of OLEDs.
  • said combination of OLEDs is a combination of three colors (eg RGB).
  • the combination of OLEDs is a combination of colors other than red, green, and blue (eg, orange and yellow-green).
  • said combination of OLEDs is a combination of two, four or more colors.
  • the device a circuit board having a first side with a mounting surface and a second opposite side and defining at least one opening; at least one OLED on the mounting surface, wherein the at least one OLED is configured to emit light, wherein the at least one OLED includes at least one organic layer including an anode, a cathode, and a light-emitting layer between the anode and the cathode; at least one OLED comprising a housing for the circuit board; at least one connector disposed at an end of said housing, said housing and said connector defining a package suitable for attachment to a lighting fixture.
  • the OLED light comprises multiple OLEDs mounted on a circuit board such that light is emitted in multiple directions. In some embodiments, some light emitted in the first direction is polarized and emitted in the second direction. In some embodiments, a reflector is used to polarize light emitted in the first direction.
  • the emissive layers of the invention can be used in screens or displays.
  • the compounds of the present invention are deposited onto a substrate using processes such as, but not limited to, vacuum evaporation, deposition, evaporation or chemical vapor deposition (CVD).
  • the substrate is a photoplate structure useful in two-sided etching to provide unique aspect ratio pixels.
  • Said screens also called masks
  • the corresponding artwork pattern design allows placement of very steep narrow tie-bars between pixels in the vertical direction as well as large and wide beveled openings in the horizontal direction.
  • the internal patterning of the pixels makes it possible to construct three-dimensional pixel openings with various aspect ratios in the horizontal and vertical directions. Further, the use of imaged "stripes" or halftone circles in pixel areas protects etching in specific areas until these specific patterns are undercut and removed from the substrate. All pixel areas are then treated with a similar etch rate, but their depth varies with the halftone pattern. Varying the size and spacing of the halftone patterns allows etching with varying degrees of protection within the pixel, allowing for the localized deep etching necessary to form steep vertical bevels. . A preferred material for the evaporation mask is Invar.
  • Invar is a metal alloy that is cold rolled into long thin sheets in steel mills. Invar cannot be electrodeposited onto a spin mandrel as a nickel mask.
  • a suitable and low-cost method for forming the open areas in the deposition mask is by wet chemical etching.
  • the screen or display pattern is a matrix of pixels on a substrate.
  • screen or display patterns are fabricated using lithography (eg, photolithography and e-beam lithography).
  • the screen or display pattern is processed using wet chemical etching.
  • the screen or display pattern is fabricated using plasma etching.
  • An OLED display is generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels.
  • each cell panel on the mother panel forms a thin film transistor (TFT) having an active layer and source/drain electrodes on a base substrate, and the TFT is coated with a planarization film, a pixel electrode, a light emitting layer , a counter electrode and an encapsulation layer, are sequentially formed and cut from the mother panel.
  • TFT thin film transistor
  • An OLED display is generally manufactured by forming a large mother panel and then cutting the mother panel into cell panels.
  • each cell panel on the mother panel forms a thin film transistor (TFT) having an active layer and source/drain electrodes on a base substrate, and the TFT is coated with a planarization film, a pixel electrode, a light emitting layer , a counter electrode and an encapsulation layer, are sequentially formed and cut from the mother panel.
  • TFT thin film transistor
  • an organic light emitting diode (OLED) display comprising: forming a barrier layer on the base substrate of the mother panel; forming a plurality of display units on the barrier layer in cell panel units; forming an encapsulation layer over each of the display units of the cell panel; and applying an organic film to the interfaces between the cell panels.
  • the barrier layer is an inorganic film, eg, made of SiNx, and the edges of the barrier layer are covered with an organic film, made of polyimide or acrylic.
  • the organic film helps the mother panel to be softly cut into cell panels.
  • a thin film transistor (TFT) layer has an emissive layer, a gate electrode, and source/drain electrodes.
  • Each of the plurality of display units may have a thin film transistor (TFT) layer, a planarization film formed on the TFT layer, and a light emitting unit formed on the planarization film, and The applied organic film is made of the same material as that of the planarizing film, and is formed at the same time as the planarizing film is formed.
  • the light-emitting unit is coupled with the TFT layer by a passivation layer, a planarizing film therebetween, and an encapsulation layer that covers and protects the light-emitting unit.
  • the organic film is not connected to the display unit or encapsulation layer.
  • each of the organic film and the planarizing film may include one of polyimide and acrylic.
  • the barrier layer may be an inorganic film.
  • the base substrate may be formed of polyimide.
  • the method further includes attaching a carrier substrate made of a glass material to another surface of a base substrate made of polyimide before forming a barrier layer on the other surface of the base substrate; separating the carrier substrate from the base substrate prior to cutting along the interface.
  • the OLED display is a flexible display.
  • the passivation layer is an organic film placed on the TFT layer to cover the TFT layer.
  • the planarizing film is an organic film formed over a passivation layer.
  • the planarizing film is formed of polyimide or acrylic, as is the organic film formed on the edge of the barrier layer. In some embodiments, the planarizing film and the organic film are formed simultaneously during the manufacture of an OLED display. In some embodiments, the organic film may be formed on the edge of the barrier layer such that a portion of the organic film is in direct contact with the base substrate and a remaining portion of the organic film is , in contact with the barrier layer while surrounding the edges of the barrier layer.
  • the emissive layer comprises a pixel electrode, a counter electrode, and an organic emissive layer disposed between the pixel electrode and the counter electrode.
  • the pixel electrodes are connected to source/drain electrodes of the TFT layer.
  • a suitable voltage is formed between the pixel electrode and the counter electrode, causing the organic light emitting layer to emit light, thereby displaying an image. is formed.
  • An image forming unit having a TFT layer and a light emitting unit is hereinafter referred to as a display unit.
  • the encapsulation layer that covers the display unit and prevents the penetration of external moisture may be formed into a thin encapsulation structure in which organic films and inorganic films are alternately laminated.
  • the encapsulation layer has a thin film-like encapsulation structure in which multiple thin films are stacked.
  • the organic film applied to the interface portion is spaced apart from each of the plurality of display units.
  • the organic film is formed such that a portion of the organic film is in direct contact with the base substrate and the remaining portion of the organic film is in contact with the barrier layer while surrounding the edges of the barrier layer. be done.
  • the OLED display is flexible and uses a flexible base substrate made of polyimide.
  • the base substrate is formed on a carrier substrate made of glass material, and then the carrier substrate is separated.
  • a barrier layer is formed on the surface of the base substrate opposite the carrier substrate.
  • the barrier layer is patterned according to the size of each cell panel. For example, a base substrate is formed on all surfaces of a mother panel, while barrier layers are formed according to the size of each cell panel, thereby forming grooves at the interfaces between the barrier layers of the cell panels. Each cell panel can be cut along the groove.
  • the manufacturing method further comprises cutting along the interface, wherein a groove is formed in the barrier layer, at least a portion of the organic film is formed with the groove, and the groove is Does not penetrate the base substrate.
  • a TFT layer of each cell panel is formed, and a passivation layer, which is an inorganic film, and a planarization film, which is an organic film, are placed on and cover the TFT layer.
  • the planarizing film eg made of polyimide or acrylic
  • the interface grooves are covered with an organic film, eg made of polyimide or acrylic. This prevents cracking by having the organic film absorb the impact that occurs when each cell panel is cut along the groove at the interface.
  • the grooves at the interfaces between the barrier layers are coated with an organic film to absorb shocks that might otherwise be transmitted to the barrier layers, so that each cell panel is softly cut and the barrier layers It may prevent cracks from forming.
  • the organic film covering the groove of the interface and the planarizing film are spaced apart from each other. For example, when the organic film and the planarizing film are connected to each other as a single layer, external moisture may enter the display unit through the planarizing film and the portion where the organic film remains. The organic film and planarizing film are spaced from each other such that the organic film is spaced from the display unit.
  • the display unit is formed by forming a light-emitting unit and an encapsulating layer is placed over the display unit to cover the display unit.
  • the carrier substrate carrying the base substrate is separated from the base substrate.
  • the carrier substrate separates from the base substrate due to the difference in coefficient of thermal expansion between the carrier substrate and the base substrate.
  • the mother panel is cut into cell panels.
  • the mother panel is cut along the interfaces between the cell panels using a cutter.
  • the interface groove along which the mother panel is cut is coated with an organic film so that the organic film absorbs impact during cutting.
  • the barrier layer can be prevented from cracking during cutting. In some embodiments, the method reduces the reject rate of the product and stabilizes its quality.
  • Another embodiment includes a barrier layer formed on a base substrate, a display unit formed on the barrier layer, an encapsulation layer formed on the display unit, and an organic layer applied to the edges of the barrier layer.
  • An OLED display comprising a film.
  • the features of the present invention will be explained more specifically below with reference to Synthesis Examples, Test Examples, and Examples.
  • the materials, processing details, processing procedures, etc. described below can be changed as appropriate without departing from the gist of the present invention. Therefore, the scope of the present invention should not be construed to be limited by the specific examples shown below.
  • the emission characteristics were evaluated using a source meter (manufactured by Keithley: 2400 series), a semiconductor parameter analyzer (manufactured by Agilent Technologies: E5273A), an optical power meter measuring device (manufactured by Newport: 1930C), and an optical spectrometer.
  • reaction solution was cooled to room temperature and toluene was removed.
  • the solid obtained was washed with water and methanol and dried.
  • Example 1 Each thin film was laminated at a degree of vacuum of 5.0 ⁇ 10 ⁇ 5 Pa by a vacuum deposition method on a glass substrate on which an anode made of indium tin oxide (ITO) with a thickness of 50 nm was formed.
  • ITO indium tin oxide
  • HAT-CN was formed to a thickness of 10 nm on ITO
  • NPD was formed thereon to a thickness of 30 nm.
  • Tris-PCz was formed to a thickness of 10 nm.
  • the delayed fluorescent material (TADF10), the fluorescent material (E35), and the compound 1 were co-deposited from different vapor deposition sources to form a layer with a thickness of 40 nm to form a light-emitting layer.
  • the concentrations of the delayed fluorescence material, the fluorescence material, and Compound 1 in the light-emitting layer were 40% by mass, 0.5% by mass, and 59.5% by mass, respectively.
  • Liq and SF3-TRZ were co-deposited from different vapor deposition sources to form a layer with a thickness of 30 nm.
  • the concentrations of Liq and SF3-TRZ in this layer were 30% and 70% by weight, respectively.
  • Liq was formed to a thickness of 2 nm, and then aluminum (Al) was vapor-deposited to a thickness of 100 nm to form a cathode, thereby obtaining an organic electroluminescence device (EL device 1).
  • Comparative example 1 An organic electroluminescence device (comparative EL device 1) was produced by performing the same steps as in Example 1, except that Comparative Compound 1 was used instead of Compound 1.
  • Example 2 An organic electroluminescence device (EL device 2) was produced by performing the same steps as in Example 1, except that compound 2 was used instead of compound 1. It was confirmed that the driving voltage of the EL element 2 was lower than that of the comparative EL element 1 .
  • Example 3 An organic electroluminescence device (EL device 3) was produced by performing the same steps as in Comparative EL device 1, except that Tris-PCz was changed to Compound 2. It was confirmed that the EL element 3 also had a longer element life than the comparative EL element 1.
  • the compound of the present invention is useful as various materials (particularly charge transport materials) used in light-emitting devices, and can be used, for example, as host materials for doping delayed fluorescence materials.
  • the properties of organic light-emitting devices such as organic electroluminescence devices can be improved. Therefore, the present invention has high industrial applicability.

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Abstract

Composé représenté par D-Ar-Z qui est utile en tant que matériau hôte pour des éléments luminescents organiques. D représente un groupe donneur, Ar représente un groupe arylène ou un groupe biphénylylène, et Z représente un groupe benzofurodibenzofuryle, un groupe benzothiénodibenzothiényle, etc.
PCT/JP2022/015885 2021-04-26 2022-03-30 Matériau de transport de charge, composition et élément luminescent organique WO2022230574A1 (fr)

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YUN JU HUI, LEE KYUNG HYUNG, LEE JUN YEOB, HONG WAN PYO: "Benzofurodibenzofuran as a universal chemical platform of highly efficient sky-blue thermally activated delayed fluorescence emitters and hosts", CHEMICAL ENGENEERING JOURNAL, ELSEVIER, AMSTERDAM, NL, vol. 411, 1 May 2021 (2021-05-01), AMSTERDAM, NL , pages 128550, XP055980422, ISSN: 1385-8947, DOI: 10.1016/j.cej.2021.128550 *

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