WO2015072537A1 - Matériau électroluminescent, élément électroluminescent organique, et composé - Google Patents

Matériau électroluminescent, élément électroluminescent organique, et composé Download PDF

Info

Publication number
WO2015072537A1
WO2015072537A1 PCT/JP2014/080162 JP2014080162W WO2015072537A1 WO 2015072537 A1 WO2015072537 A1 WO 2015072537A1 JP 2014080162 W JP2014080162 W JP 2014080162W WO 2015072537 A1 WO2015072537 A1 WO 2015072537A1
Authority
WO
WIPO (PCT)
Prior art keywords
general formula
compound
atom
group
substituent
Prior art date
Application number
PCT/JP2014/080162
Other languages
English (en)
Japanese (ja)
Inventor
真樹 沼田
琢麿 安田
安達　千波矢
Original Assignee
国立大学法人九州大学
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 国立大学法人九州大学 filed Critical 国立大学法人九州大学
Priority to JP2015547802A priority Critical patent/JP6392240B2/ja
Publication of WO2015072537A1 publication Critical patent/WO2015072537A1/fr

Links

Images

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • 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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • 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
    • 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 light emitting material and an organic light emitting device using the compound.
  • organic light emitting devices such as organic electroluminescence devices (organic EL devices)
  • organic electroluminescence devices organic electroluminescence devices
  • various efforts have been made to increase the light emission efficiency by newly developing and combining electron transport materials, hole transport materials, light emitting materials, and the like constituting the organic electroluminescence element.
  • research on organic electroluminescence devices using a compound having a structure in which a substituent such as a carbazolyl group is bonded to a tricyclic structure having a heteraborine ring containing a boron atom and another heteroatom can be seen.
  • Non-Patent Document 1 describes the results of studying luminescence characteristics of a compound having a heteraboline ring containing a boron atom and a nitrogen atom. According to the document, it was described that when a cyclohexane solution or a solid film of a compound having the following structure was irradiated with excitation light, light emission was observed in the visible region (Hex n represents an n-hexyl group, and Tip represents Represents a 2,4,6-triisopropylphenyl group). However, Non-Patent Document 1 does not describe a compound in which a heteroatom of a heteraboline ring is changed to a heteroatom other than a nitrogen atom such as an oxygen atom or a sulfur atom.
  • Patent Document 1 discloses a compound having a tricyclic structure having a heterolabrin ring represented by the following general formula.
  • R 1 in the following general formula is a group containing two or more aryl groups or heteroaryl groups
  • R 3 and R 4 represent 1 to 5 substituents
  • R 2 to R 4 represent a hydrogen atom, an alkyl group
  • R 1 in the following general formula is a 2,4,6-triphenylphenyl group
  • R 2 is a phenyl group
  • R 3 and R 4 are hydrogen atoms
  • Patent Document 1 does not describe the light emission characteristics of the compound represented by this general formula, nor does it describe a compound in which the heteroatom of the heterolabrin ring is changed to a heteroatom other than a nitrogen atom. .
  • Non-Patent Document 2 describes the results of studying the emission characteristics of a compound having a heteraboline ring containing a boron atom and other heteroatoms, and light emission in the visible region was observed in a cyclohexane solution of a compound having the following structure. It is described.
  • R represents a hydrogen atom or a methyl group
  • E represents an N-methyl group or a sulfur atom
  • Mes represents a mesityl group.
  • Non-Patent Document 1 does not describe a compound in which R is a substituted amino group such as a carbazolyl group.
  • Non-Patent Document 1 discloses that a compound in which a carbazolyl group is introduced into a tricyclic structure having a heteraboline ring (azaborin ring) containing a boron atom and a nitrogen atom emits light in the visible region.
  • azaborin ring a heteraboline ring
  • the inventors actually evaluated the light emission characteristics of a compound in which a carbazolyl group substituted with a carbazolyl group, a methyl group, or the like was introduced into a tricyclic structure having an azaborin ring, the light emission characteristics can be sufficiently satisfied. It was proved that it was not (see Comparative Examples 1 to 3 below).
  • Non-Patent Document 2 it is described in Non-Patent Document 2 that light emission was observed in the visible region of a compound having a tricyclic structure having a heteraboline ring containing a boron atom and a sulfur atom.
  • Non-Patent Document 2 does not describe a compound in which a substituted amino group such as a carbazole group is bonded to a tricyclic structure having a heterolabrin ring. For this reason, the usefulness as a light-emitting material of a compound in which a substituted amino group such as a carbazolyl group is bonded to a tricyclic structure having a heteraboline ring containing a boron atom and an oxygen atom or a sulfur atom cannot be predicted.
  • the present inventors have further investigated the usefulness of a compound having a heteraboline ring containing a boron atom and an oxygen atom or sulfur atom as a luminescent material, and found a compound having excellent luminescent properties. Aimed at research. And the general formula of the compound useful as a luminescent material was derived, and the earnest examination was advanced for the purpose of generalizing the structure of the organic light emitting element with high luminous efficiency.
  • the present inventors have found that compounds having a specific structure among the compounds having a heteraboline ring containing a boron atom and an oxygen atom or a sulfur atom have excellent properties as a luminescent material.
  • a group of compounds is useful as a delayed fluorescent material, and it has been clarified that an organic light-emitting device having high emission efficiency can be provided at low cost. Based on these findings, the present inventors have provided the following present invention as means for solving the above problems.
  • a light emitting material comprising a compound represented by the following general formula (1).
  • X represents an oxygen atom or a sulfur atom.
  • R 1 ⁇ R 8 each independently represent a hydrogen atom or a substituent. However, at least one of R 1 to R 8 is each independently a group represented by any one of the following general formulas (2) to (7).
  • R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7 , R 7 and R 8 , R 8 and R 9 , R 9 and R 1 are bonded to each other Thus, a ring structure may be formed.
  • R 9 represents a substituent.
  • R 9 contains an atom having a lone pair of electrons that does not form a single bond with a boron atom
  • the atom may be coordinated with the boron atom to form a cyclic structure.
  • L 12 to L 17 each independently represents a single bond or a divalent linking group
  • * represents a bonding site to the benzene ring in the general formula (1).
  • R 11 to R 20 , R 21 to R 28 , R 31 to R 38 , R 3a , R 3b , R 41 to R 48 , R 4a , R 51 to R 58 , R 61 to R 68 are each independently hydrogen Represents an atom or substituent.
  • R 9 in the general formula (1) is a group represented by the following general formula (a).
  • * represents the bonding site to the boron atom in the general formula (1).
  • R 9a , R 9b , R 9c , R 9d and R 9e each independently represent a hydrogen atom or a substituent.
  • R 9a and R 9b , R 9b and R 9c , R 9c and R 9d , and R 9d and R 9e may be bonded to each other to form a cyclic structure.
  • X ′ represents an oxygen atom or a sulfur atom.
  • R 1 ′ to R 8 ′ each independently represents a hydrogen atom or a substituent. However, at least one of R 1 ′ to R 8 ′ is a group independently represented by any one of the following general formulas (2 ′) to (7 ′).
  • R 1 'and R 2', R 2 'and R 3', R 3 'and R 4', R 5 'and R 6', R 6 'and R 7', R 7 'and R 8', R 8 'And R 9 ' and R 9 'and R 1 ' may be bonded to each other to form a cyclic structure.
  • R 9 ′ represents a substituent. When R 9 ′ includes an atom having a lone pair of electrons that does not form a single bond with a boron atom, the atom may be coordinated with the boron atom to form a cyclic structure.
  • L 12 ′ to L 17 ′ each independently represents a single bond or a divalent linking group, and * represents a bond to the benzene ring in the general formula (1 ′).
  • the compound of the present invention is useful as a light emitting material.
  • the compounds of the present invention include those that emit delayed fluorescence.
  • An organic light emitting device using the compound of the present invention as a light emitting material can realize high luminous efficiency.
  • 2 is an emission spectrum of a solution of compound 5 in Example 1.
  • 2 is an emission spectrum of a thin film type organic photoluminescence device of Compound 5 of Example 1.
  • 2 is a transient decay curve of a solution of compound 5 of Example 1. It is the emission spectrum of the solution of the compound 6 of Example 2, and a thin film type organic photoluminescent element.
  • 2 is an emission spectrum of a thin film type organic photoluminescence device of Compound 6 of Example 2.
  • 4 is a transient decay curve of a solution of compound 6 of Example 2.
  • 2 is an emission spectrum of a solution of the compound 18 of Example 3.
  • 3 is a transient decay curve of a solution of the compound 18 of Example 3.
  • 4 is an emission spectrum of a solution of the compound 59 of Example 4.
  • 7 is an emission spectrum of a solution of the compound 65 of Example 5.
  • 7 is an emission spectrum of a solution of the compound 67 of Example 6.
  • 4 is an emission spectrum of a solution of compound 156 of Example 7.
  • 4 is a transient decay curve of a solution of compound 156 of Example 7.
  • 2 is an emission spectrum of a solution of Comparative Compound A of Comparative Example 1.
  • 2 is a transient decay curve of a solution of Comparative Compound A of Comparative Example 1.
  • 3 is an emission spectrum of a solution of Comparative Compound B of Comparative Example 2.
  • 4 is a transient decay curve of a solution of Comparative Compound B of Comparative Example 2.
  • 2 is an emission spectrum of a solution of Comparative Compound C of Comparative Example 3.
  • 4 is a transient decay curve of a solution of Comparative Compound C of Comparative Example 3.
  • 2 is an emission spectrum of an organic electroluminescent element of the compound 5 of Example 11.
  • 6 is a graph showing current density-external quantum efficiency characteristics of an organic electroluminescent device of Compound 5 of Example 11.
  • 7 is an emission spectrum of an organic electroluminescent element of the compound 6 of Example 12.
  • 10 is a graph showing current density-external quantum efficiency characteristics of an organic electroluminescence device of Compound 6 of Example 12.
  • a numerical range represented by using “to” means a range including numerical values described before and after “to” as a lower limit value and an upper limit value.
  • the isotope species of the hydrogen atom present in the molecule of the compound used in the present invention is not particularly limited. For example, all the hydrogen atoms in the molecule may be 1 H, or a part or all of them are 2 H. (Deuterium D) may be used.
  • the luminescent material of the present invention is characterized by comprising a compound represented by the following general formula (1).
  • X represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom.
  • R 1 to R 8 each independently represents a hydrogen atom or a substituent. However, at least one of R 1 to R 8 is each independently a group represented by any one of the following general formulas (2) to (7). The group represented by any of the following general formulas (2) to (7) may be only one of R 1 to R 8 , or may be two or more.
  • any one of R 2 , R 3 , R 6 and R 7 Is preferably a group represented by any one of the following general formulas (2) to (7)
  • R 3 or R 6 is a group represented by any one of the following general formulas (2) to (7). More preferably.
  • any one of the following general formulas (2) to (7) Is preferably at least one of R 1 to R 4 and at least one of R 5 to R 8 .
  • the groups represented by any of the following general formulas (2) to (7) are 1 to 3 of R 1 to R 4 and 1 to 3 of R 5 to R 8. It is preferably 1 or 2 of R 1 to R 4 , and more preferably 1 or 2 of R 5 to R 8 .
  • R 1 to R 4 are represented by any of the general formulas (2) to (7), and R 5 to R 8 are represented by any of the general formulas (2) to (7).
  • the number of groups may be the same or different, but is preferably the same.
  • R 1 to R 4 at least one of R 2 or R 3 is preferably a group represented by any one of the general formulas (2) to (7), and at least R 3 is a group represented by the general formula (2) A group represented by any one of (7) to (7) is more preferable.
  • R 5 to R 8 at least one of R 6 or R 7 is preferably a group represented by any one of the general formulas (2) to (7), and at least R 6 is a group represented by the general formula ( A group represented by any one of 2) to (7) is more preferable.
  • Preferred compounds are those in which R 3 and R 6 in the general formula (1) are groups represented by any one of the general formulas (2) to (7), and R 2 and R 7 in the general formula (1) are general.
  • a more preferred compound is a compound in which R 3 and R 6 are groups represented by any one of the general formulas (2) to (7).
  • the groups represented by any of the plurality of general formulas (2) to (7) present in the general formula (1) may be the same or different, but are preferably the same.
  • the group represented by the general formula (1) has a symmetrical structure. That is, R 1 and R 8 , R 2 and R 7 , R 3 and R 6 , and R 4 and R 5 are preferably the same.
  • L 12 to L 17 each independently represent a single bond or a divalent linking group, and preferably a single bond.
  • examples of the divalent linking group include an aromatic hydrocarbon ring group having 6 to 18 carbon atoms and a heteroaromatic hydrocarbon ring group having 6 to 18 ring members. Can be mentioned.
  • Preferred linking groups are a phenylene group, a biphenylene group, a fluorenylene group, a triphenylenylene group, and a thiophenylene group, a more preferred linking group is a phenylene group, and a more preferred linking group is a 1,4-phenylene group. .
  • These linking groups may have a substituent introduced therein.
  • the explanation and preferred range of the substituent that can be introduced into the linking group the explanation and preferred range of the substituent that can be taken by the following R 1 to R 8 and the like can be referred to.
  • R 11 to R 20 , R 21 to R 28 , R 31 to R 38 , R 3a , R 3b , R 41 to R 48 , R 4a , R 51 to R 58 , R 61 to R 68 each independently represents a hydrogen atom or a substituent.
  • R 11 to R 20 , R 21 to R 28 , R 31 to R 38 , R 3a , R 3b , R 41 to R 48 , R 4a , R 51 to R 58 , R All of 61 to R 68 may be unsubstituted (that is, a hydrogen atom), but R 11 to R 20 , R 21 to R 28 , R 31 to R 38 , R 3a and R 3b , R 41 to R 48 , R 51 to R 58 , and R 61 to R 68 are preferably a substituent, and R 13 and R 18 , R 23 and R 26 , R 33 and R 36 , R 3a and More preferably, at least one of the respective groups of R 3b , R 43 and R 46 , R 53 and R 56 , R 63 and R 66 is a substituent. In each of the general formulas (2) to (7), when there are two or more substituents, these substituents may be the same or different.
  • R 11 to R 20 , R 21 to R 28 , R 31 to R 38 , R 3a , R 3b , R 41 to R 48 , R 4a , R 51 to R 58 , R 61 to R 68 , R 1 to R 8 can be substituted with a substituent that can be introduced into L 12 to L 17 , for example, a hydroxy group, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, 20 alkoxy groups, alkylthio groups having 1 to 20 carbon atoms, alkyl-substituted amino groups having 1 to 20 carbon atoms, acyl groups having 2 to 20 carbon atoms, aryl groups having 6 to 40 carbon atoms, heterocycles having 3 to 40 carbon atoms An aryl group, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkoxycarbonyl group having 2 to 10 carbon atom
  • substituents are a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, carbon A substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms, and a dialkyl-substituted amino group having 1 to 20 carbon atoms.
  • substituents are a halogen atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, carbon A substituted or unsubstituted heteroaryl group having 3 to 40 carbon atoms, and a dialkyl-substituted amino group having 1 to 20 carbon
  • substituents are a fluorine atom, a chlorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, and a substituted group having 6 to 15 carbon atoms.
  • it is an unsubstituted aryl group or a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.
  • the cyclic structure may be an aromatic ring or an alicyclic ring, may contain a hetero atom, and the cyclic structure may be a condensed ring of two or more rings.
  • the hetero atom here is preferably selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom.
  • Examples of cyclic structures formed include benzene ring, naphthalene ring, pyridine ring, pyridazine ring, pyrimidine ring, pyrazine ring, pyrrole ring, imidazole ring, pyrazole ring, triazole ring, imidazoline ring, oxazole ring, isoxazole ring, thiazole And a ring, an isothiazole ring, a cyclohexadiene ring, a cyclohexene ring, a cyclopentaene ring, a cycloheptatriene ring, a cycloheptadiene ring, and a cycloheptaene ring.
  • R 11 to R 20 , R 21 to R 28 , R 31 to R 38 , R 3a , R 3b , R 41 to R 48 , R 4a , R 51 to R 58 , and R 61 to R 68 are each independently A group represented by any one of the general formulas (2) to (7) is also preferable.
  • R 1 to R 8 may be, for example, at least one selected from the groups represented by any of the general formulas (3) to (7), and at least one of the general formulas (4) to (7 ) May be selected.
  • R 1 ⁇ R 8 is a group represented by the general formula (4)
  • R 3a and R 3b are preferably bonded to each other to form a cyclic structure.
  • the cyclic structure is preferably a tricyclic structure such as a fluorene ring, a xanthene ring, or a thioxanthene ring.
  • R 9 represents a substituent.
  • R 9 is preferably a substituted or unsubstituted phenyl group represented by the following general formula (8).
  • R 9a , R 9b , R 9c , R 9d and R 9e each independently represent a hydrogen atom or a substituent.
  • the number of substituents is not particularly limited, and all of R 9a , R 9b , R 9c , R 9d , and R 9e may be unsubstituted (that is, a hydrogen atom), but R 9a , R 9c , and R 9e At least one of them is preferably a substituent, and R 9a and R 9e are more preferably substituents.
  • these substituents may be the same or different.
  • R 9a and R 9b , R 9b and R 9c , R 9c and R 9d , and R 9d and R 9e may be bonded to each other to form a cyclic structure.
  • R 9a , R 9b , R 9c , R 9d , and R 9e may take, see the explanations and preferred ranges of the substituents that can be taken by R 1 to R 8 below.
  • R 1 to R 8 For the explanation and preferred examples of the cyclic structure, reference can be made to the explanation and preferred examples of the cyclic structure formed by combining R 1 and R 2 in the general formula (1).
  • R 9 is a substituent that includes an atom that does not form a single bond with a boron atom and has a lone pair
  • the atom coordinates with the boron atom to form a cyclic structure. It may be.
  • the atoms that do not form a single bond with the boron atom and have a lone pair include oxygen atoms and nitrogen atoms.
  • the cyclic structure formed by coordination bonding of the atom with a boron atom is preferably a 5- to 7-membered ring, and more preferably a 5- or 6-membered ring.
  • the following compounds 177 to 186 can be referred to. In these compounds, an oxygen atom or a nitrogen atom that does not form a single bond with a boron atom is coordinated with the boron atom to form a 5- or 6-membered ring.
  • 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 vapor deposition. Preferably, it is preferably 1200 or less, more preferably 1000 or less, and even more preferably 800 or less.
  • the lower limit of the molecular weight is the molecular weight of the minimum compound represented by the general formula (1).
  • the compound represented by the general formula (1) may be formed by a coating method regardless of the molecular weight. If a coating method is used, a film can be formed even with a compound having a relatively large molecular weight.
  • a compound containing a plurality of structures represented by the general formula (1) in the molecule as a light emitting material.
  • a polymer obtained by previously polymerizing a polymerizable group in the structure represented by the general formula (1) and polymerizing the polymerizable group as a light emitting material.
  • a monomer containing a polymerizable functional group in any of R 1 to R 9 in the general formula (1) and polymerizing it alone or copolymerizing with other monomers, It is conceivable to obtain a polymer having a repeating unit and use the polymer as a light emitting material.
  • dimers and trimers are obtained by reacting compounds having a structure represented by the general formula (1) and used as a luminescent material.
  • Examples of the polymer having a repeating unit containing a structure represented by the general formula (1) include a polymer containing a structure represented by the following general formula (9) or (10).
  • Q represents a group including the structure represented by General Formula (1)
  • L 1 and L 2 represent a linking group.
  • the linking group preferably has 0 to 20 carbon atoms, more preferably 1 to 15 carbon atoms, and still more preferably 2 to 10 carbon atoms. And preferably has a structure represented by - linking group -X 11 -L 11.
  • X 11 represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom.
  • L 11 represents a linking group, preferably a substituted or unsubstituted alkylene group, or a substituted or unsubstituted arylene group, and a substituted or unsubstituted alkylene group having 1 to 10 carbon atoms, or a substituted or unsubstituted group A phenylene group is more preferable.
  • R 101 , R 102 , R 103 and R 104 each independently represent a substituent.
  • it is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a halogen atom, more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms.
  • An unsubstituted alkoxy group having 1 to 3 carbon atoms, a fluorine atom, and a chlorine atom and more preferably an unsubstituted alkyl group having 1 to 3 carbon atoms and an unsubstituted alkoxy group having 1 to 3 carbon atoms.
  • the linking group represented by L 1 and L 2 is any one of R 1 to R 8 in the structure of the general formula (1) constituting Q, any one of R 11 to R 20 in the general formula (2), Any one of R 21 to R 28 in the structure of formula (3), any of R 31 to R 38 in the structure of general formula (4), any of R 41 to R 48 in the structure of general formula (5), It can be bonded to any one of R 51 to R 58 of the structure of the general formula (6) and any of R 61 to R 68 of the structure of the general formula (7).
  • Two or more linking groups may be linked to one Q to form a crosslinked structure or a network structure.
  • repeating unit examples include structures represented by the following formulas (11) to (14).
  • a hydroxy group is introduced into any one of R 1 to R 9 of the structure of the general formula (1), and this is used as a linker as described below. It can be synthesized by reacting a compound to introduce a polymerizable group and polymerizing the polymerizable group.
  • the polymer containing the structure represented by the general formula (1) in the molecule may be a polymer composed only of repeating units having the structure represented by the general formula (1), or other structures may be used. It may be a polymer containing repeating units.
  • the repeating unit having a structure represented by the general formula (1) contained in the polymer may be a single type or two or more types. Examples of the repeating unit not having the structure represented by the general formula (1) include those derived from monomers used in ordinary copolymerization. Examples thereof include a repeating unit derived from a monomer having an ethylenically unsaturated bond such as ethylene and styrene.
  • X ′ represents an oxygen atom or a sulfur atom.
  • R 1 ′ to R 8 ′ each independently represents a hydrogen atom or a substituent. However, at least one of R 1 ′ to R 8 ′ is a group independently represented by the following general formulas (2 ′) to (7 ′).
  • R 1 'and R 2', R 2 'and R 3', R 3 'and R 4', R 5 'and R 6', R 6 'and R 7', R 7 'and R 8', R 8 'And R 9 ' and R 9 'and R 1 ' may be bonded to each other to form a cyclic structure.
  • R 9 ′ represents a substituent. When R 9 ′ includes an atom having a lone pair of electrons that does not form a single bond with a boron atom, the atom may be coordinated with the boron atom to form a cyclic structure.
  • L 12 ′ to L 17 ′ each independently represents a single bond or a divalent linking group
  • * represents a binding site to the benzene ring in the general formula (1 ′).
  • R 1 ′ to R 8 ′ in general formula (1 ′) and R 11 ′ to R 20 ′, R 21 ′ to R 28 ′, R 31 ′ to R 38 in general formulas (2 ′) to (7 ′) R, R 3a , R 3b ′, R 41 ′ to R 48 ′, R 4a ′, R 51 ′ to R 58 ′, R 61 ′ to R 68 ′ are explained in general formula (1).
  • the description of the compound represented by can be referred to.
  • A represents a halogen atom, and examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and a chlorine atom, a bromine atom, and an iodine atom are preferable.
  • the above reaction is an application of a known reaction, and known reaction conditions can be appropriately selected and used. The details of the above reaction can be referred to the synthesis examples described below.
  • the compound represented by the general formula (1 ′) can also be synthesized by combining other known synthesis reactions.
  • the compound represented by the general formula (1) of the present invention is useful as a light emitting material of an organic light emitting device. For this reason, the compound represented by General formula (1) of this invention can be effectively used as a luminescent material for the light emitting layer of an organic light emitting element.
  • the compound represented by the general formula (1) includes a delayed fluorescent material (delayed phosphor) that emits delayed fluorescence. That is, the present invention relates to a delayed phosphor having a structure represented by the general formula (1), an invention using a compound represented by the general formula (1) as a delayed phosphor, and a general formula (1).
  • An invention of a method for emitting delayed fluorescence using the represented compound is also provided.
  • An organic light emitting device using such a compound as a light emitting material emits delayed fluorescence and has a feature of high luminous efficiency. The principle will be described below by taking an organic electroluminescence element as an example.
  • the organic electroluminescence element carriers are injected into the light emitting material from both positive and negative electrodes to generate an excited light emitting material and emit light.
  • 25% of the generated excitons are excited to the excited singlet state, and the remaining 75% are excited to the excited triplet state. Therefore, the use efficiency of energy is higher when phosphorescence, which is light emission from an excited triplet state, is used.
  • the excited triplet state has a long lifetime, energy saturation occurs due to saturation of the excited state and interaction with excitons in the excited triplet state, and in general, the quantum yield of phosphorescence is often not high.
  • delayed fluorescent materials after energy transition to an excited triplet state due to intersystem crossing, etc., are then crossed back to an excited singlet state due to triplet-triplet annihilation or absorption of thermal energy, and emit fluorescence.
  • a thermally activated delayed fluorescent material by absorption of thermal energy is particularly useful.
  • excitons in the excited singlet state emit fluorescence as usual.
  • excitons in the excited triplet state absorb heat generated by the device and cross between the excited singlets to emit fluorescence.
  • the light is emitted from the excited singlet, the light is emitted at the same wavelength as the fluorescence, but the light lifetime (luminescence lifetime) generated by the reverse intersystem crossing from the excited triplet state to the excited singlet state is normal. Since the fluorescence becomes longer than the fluorescence and phosphorescence, it is observed as fluorescence delayed from these. This can be defined as delayed fluorescence. If such a heat-activated exciton transfer mechanism is used, the ratio of the compound in an excited singlet state, which normally generated only 25%, is increased to 25% or more by absorbing thermal energy after carrier injection. It can be raised.
  • the heat of the device will sufficiently cause intersystem crossing from the excited triplet state to the excited singlet state and emit delayed fluorescence. Efficiency can be improved dramatically.
  • the compound represented by the general formula (1) of the present invention as a light-emitting material of a light-emitting layer, excellent organic light-emitting devices such as an organic photoluminescence device (organic PL device) and an organic electroluminescence device (organic EL device) Can be provided.
  • the compound represented by the general formula (1) of the present invention may have a function of assisting light emission of another light emitting material included in the light emitting layer as a so-called assist dopant. That is, the compound represented by the general formula (1) of the present invention contained in the light emitting layer includes the lowest excitation singlet energy level of the host material contained in the light emitting layer and the lowest excitation of other light emitting materials contained in the light emitting layer.
  • the organic photoluminescence element 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 an organic layer is formed at least between an anode, a cathode, and an anode and a 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. Examples of such other organic layers include a hole transport layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an exciton blocking layer.
  • 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.
  • FIG. 1 A specific example of the structure of an organic electroluminescence element is shown in FIG.
  • 1 is a substrate
  • 2 is an anode
  • 3 is a hole injection layer
  • 4 is a hole transport layer
  • 5 is a light emitting layer
  • 6 is an electron transport layer
  • 7 is a cathode.
  • each member and each layer of an organic electroluminescent element are demonstrated.
  • substrate and a light emitting layer corresponds also to the board
  • the organic electroluminescence device of the present invention is preferably supported on a substrate.
  • the substrate is not particularly limited and may be any substrate conventionally used for organic electroluminescence elements.
  • a substrate made of glass, transparent plastic, quartz, silicon, or the like can be used.
  • an electrode material made of a metal, an alloy, an electrically conductive compound, or a mixture thereof having a high work function (4 eV or more) is preferably used.
  • electrode materials include metals such as Au, and conductive transparent materials such as CuI, indium tin oxide (ITO), SnO 2 , and ZnO.
  • conductive transparent materials such as CuI, indium tin oxide (ITO), SnO 2 , and ZnO.
  • an amorphous material such as IDIXO (In 2 O 3 —ZnO) that can form a transparent conductive film may be used.
  • a thin film may be formed by vapor deposition or sputtering of these electrode materials, and a pattern of a desired shape may be formed by photolithography, or when pattern accuracy is not so high (about 100 ⁇ m or more) ), A pattern may be formed through a mask having a desired shape at the time of vapor deposition or sputtering of the electrode material.
  • wet film-forming methods such as a printing system and a coating system, can also be used.
  • the transmittance be greater than 10%, and the sheet resistance as the anode is preferably several hundred ⁇ / ⁇ or less.
  • the film thickness depends on the material, it is usually selected in the range of 10 to 1000 nm, preferably 10 to 200 nm.
  • cathode a material having a low work function (4 eV or less) metal (referred to as an electron injecting metal), an alloy, an electrically conductive compound, and a mixture thereof as an electrode material is used.
  • electrode materials include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al 2 O 3 ) Mixtures, indium, lithium / aluminum mixtures, rare earth metals and the like.
  • a mixture of an electron injecting metal and a second metal which is a stable metal having a larger work function value than this for example, a magnesium / silver mixture
  • Suitable are a magnesium / aluminum mixture, a magnesium / indium mixture, an aluminum / aluminum oxide (Al 2 O 3 ) mixture, a lithium / aluminum mixture, aluminum and the like.
  • the cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.
  • the sheet resistance as the cathode is preferably several hundred ⁇ / ⁇ or less, and the film thickness is usually selected in the range of 10 nm to 5 ⁇ m, preferably 50 to 200 nm.
  • the emission luminance is advantageously improved.
  • a transparent or semi-transparent cathode can be produced. By applying this, an element in which both the anode and the cathode are transparent is used. Can be produced.
  • the light emitting layer is a layer that emits light after excitons are generated by recombination of holes and electrons injected from each of the anode and the cathode, and the light emitting material may be used alone for the light emitting layer. , Preferably including a luminescent material and a host material. As a luminescent material, the 1 type (s) or 2 or more types chosen from the compound group of this invention represented by General formula (1) can be used. In order for the organic electroluminescence device and the organic photoluminescence device of the present invention to exhibit high luminous efficiency, it is important to confine singlet excitons and triplet excitons generated in the light emitting material in the light emitting material.
  • a host material in addition to the light emitting material in the light emitting layer.
  • the host material an organic compound having at least one of excited singlet energy and excited triplet energy higher than that of the light emitting material of the present invention can be used.
  • singlet excitons and triplet excitons generated in the light emitting material of the present invention can be confined in the molecules of the light emitting material of the present invention, and the light emission efficiency can be sufficiently extracted.
  • high luminous efficiency can be obtained, so that host materials that can achieve high luminous efficiency are particularly limited. And can be used in the present invention.
  • the organic light emitting device or organic electroluminescent device of the present invention light emission is generated from the light emitting material of the present invention contained in the light emitting layer. This emission includes both fluorescence and delayed fluorescence. However, light emission from the host material may be partly or partly emitted.
  • the amount of the compound of the present invention, which is a light emitting material is preferably 0.1% by weight or more, more preferably 1% by weight or more, and 50% or more. It is preferably no greater than wt%, more preferably no greater than 20 wt%, and even more preferably no greater than 10 wt%.
  • the host material in the light-emitting layer is preferably an organic compound that has a hole transporting ability and an electron transporting ability, prevents the emission of longer wavelengths, and has a high glass transition temperature.
  • the injection layer is a layer provided between the electrode and the organic layer for lowering the driving voltage and improving the luminance of light emission, and includes a hole injection layer and an electron injection layer, Further, it may be present between the cathode and the light emitting layer or the electron transport layer.
  • the injection layer can be provided as necessary.
  • the blocking layer is a layer that can prevent diffusion of charges (electrons or holes) and / or excitons existing in the light emitting layer to the outside of the light emitting layer.
  • the electron blocking layer can be disposed between the light emitting layer and the hole transport layer and blocks electrons from passing through the light emitting layer toward the hole transport layer.
  • a hole blocking layer can be disposed between the light emitting layer and the electron transporting layer to prevent holes from passing through the light emitting layer toward the electron transporting layer.
  • the blocking layer can also be used to block excitons from diffusing outside the light emitting layer. That is, each of the electron blocking layer and the hole blocking layer can also function as an exciton blocking layer.
  • the term “electron blocking layer” or “exciton blocking layer” as used herein is used in the sense of including a layer having the functions of an electron blocking layer and an exciton blocking layer in one layer.
  • the hole blocking layer has a function of an electron transport layer in a broad sense.
  • the hole blocking layer has a role of blocking holes from reaching the electron transport layer while transporting electrons, thereby improving the recombination probability of electrons and holes in the light emitting layer.
  • the material for the hole blocking layer the material for the electron transport layer described later can be used as necessary.
  • the electron blocking layer has a function of transporting holes in a broad sense.
  • the electron blocking layer has a role to block electrons from reaching the hole transport layer while transporting holes, thereby improving the probability of recombination of electrons and holes in the light emitting layer. .
  • the exciton blocking layer is a layer for preventing excitons generated by recombination of holes and electrons in the light emitting layer from diffusing into the charge transport layer. It becomes possible to efficiently confine in the light emitting layer, and the light emission efficiency of the device can be improved.
  • the exciton blocking layer can be inserted on either the anode side or the cathode side adjacent to the light emitting layer, or both can be inserted simultaneously.
  • the layer when the exciton blocking layer is provided on the anode side, the layer can be inserted adjacent to the light emitting layer between the hole transport layer and the light emitting layer, and when inserted on the cathode side, the light emitting layer and the cathode Between the luminescent layer and the light-emitting layer.
  • a hole injection layer, an electron blocking layer, or the like can be provided between the anode and the exciton blocking layer adjacent to the anode side of the light emitting layer, and the excitation adjacent to the cathode and the cathode side of the light emitting layer can be provided.
  • an electron injection layer, an electron transport layer, a hole blocking layer, and the like can be provided.
  • the blocking layer is disposed, at least one of the excited singlet energy and the excited triplet energy of the material used as the blocking layer is preferably higher than the excited singlet energy and the excited triplet energy of the light emitting material.
  • the hole transport layer is made of a hole transport material having a function of transporting holes, and the hole transport layer can be provided as a single layer or a plurality of layers.
  • the hole transport material has any one of hole injection or transport and electron barrier properties, and may be either organic or inorganic.
  • hole transport materials that can be used include, for example, triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, Examples include amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, and conductive polymer oligomers, particularly thiophene oligomers.
  • An aromatic tertiary amine compound and an styrylamine compound are preferably used, and an aromatic tertiary amine compound is more preferably used.
  • the electron transport layer is made of a material having a function of transporting electrons, and the electron transport layer can be provided as a single layer or a plurality of layers.
  • the electron transport material (which may also serve as a hole blocking material) may have a function of transmitting electrons injected from the cathode to the light emitting layer.
  • Examples of the electron transport layer that can be used include nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, oxadiazole derivatives, and the like.
  • a thiadiazole derivative in which the oxygen atom of the oxadiazole ring is substituted with a sulfur atom, and a quinoxaline derivative having a quinoxaline ring known as an electron withdrawing group can also be used as an electron transport material.
  • a polymer material in which these materials are introduced into a polymer chain or these materials are used as a polymer main chain can also be used.
  • the compound represented by the general formula (1) may be used not only for the light emitting layer but also for layers other than the light emitting layer.
  • the compound represented by General formula (1) used for a light emitting layer and the compound represented by General formula (1) used for layers other than a light emitting layer may be same or different.
  • the compound represented by the general formula (1) may be used for the injection layer, blocking layer, hole blocking layer, electron blocking layer, exciton blocking layer, hole transporting layer, electron transporting layer, and the like. .
  • the method for forming these layers is not particularly limited, and the layer may be formed by either a dry process or a wet process.
  • the preferable material which can be used for an organic electroluminescent element is illustrated concretely.
  • the material that can be used in the present invention is not limited to the following exemplary compounds.
  • R and R 1 to R 10 in the structural formulas of the following exemplary compounds each independently represent a hydrogen atom or a substituent.
  • n represents an integer of 3 to 5.
  • the organic electroluminescent device produced by the above-described method emits light by applying an electric field between the anode and the cathode of the obtained device. At this time, if the light is emitted by excited singlet energy, light having a wavelength corresponding to the energy level is confirmed as fluorescence emission and delayed fluorescence emission. In addition, in the case of light emission by excited triplet energy, a wavelength corresponding to the energy level is confirmed as phosphorescence. Since normal fluorescence has a shorter fluorescence lifetime than delayed fluorescence, the emission lifetime can be distinguished from fluorescence and delayed fluorescence.
  • the excited triplet energy is unstable and is converted into heat and the like, and the lifetime is short and it is immediately deactivated.
  • the excited triplet energy of a normal organic compound it can be measured by observing light emission under extremely low temperature conditions.
  • the organic electroluminescence element of the present invention can be applied to any of a single element, an element having a structure arranged in an array, and a structure in which an anode and a cathode are arranged in an XY matrix. According to the present invention, an organic light emitting device with greatly improved light emission efficiency can be obtained by containing the compound represented by the general formula (1) in the light emitting layer.
  • the organic light emitting device such as the organic electroluminescence device of the present invention can be further applied to various uses. For example, it is possible to produce an organic electroluminescence display device using the organic electroluminescence element of the present invention.
  • organic electroluminescence device of the present invention can be applied to organic electroluminescence illumination and backlights that are in great demand.
  • Methyl anthranilate (349.2 g, 2310 mmol), iodobenzene (428.4 g, 2100 mmol), potassium carbonate (348.3 g, 2520 mmol), and copper iodide (20.0 g, 105 mmol) were placed in a three-necked flask under a nitrogen atmosphere. The mixture was heated and stirred at 180 ° C. After completion of the reaction, the mixture was cooled to room temperature, diluted with 500 ml of hexane, and filtered using celite.
  • the target pale yellow oily liquid (intermediate 1a) was obtained in a yield of 427.5 g and a yield of 90%.
  • This solution was washed with water using a separatory funnel and dried over anhydrous magnesium sulfate. Thereafter, the solution was filtered, concentrated, and vacuum dried (60 ° C., 6 h) to obtain an oily liquid.
  • This oily liquid was put into a three-necked flask, 960 ml of chloroform and 62.3 ml of methanesulfonic acid were added, and the mixture was refluxed for 3 hours in a nitrogen atmosphere. After cooling this mixture to room temperature, it neutralized carefully using sodium hydrogencarbonate aqueous solution, and extracted with chloroform using the separatory funnel. The obtained extract was dried over anhydrous magnesium sulfate, filtered through a silica gel pad, and concentrated.
  • the concentrate obtained by concentrating the obtained fraction was recrystallized with a mixed solvent of toluene and hexane (1: 5 ml / g).
  • the target intermediate 1b was obtained in a yield of 47.9 g and a yield of 48%.
  • This solution was washed with water using a separatory funnel and dried over anhydrous magnesium sulfate. Thereafter, the solution was filtered, concentrated, and vacuum dried (60 ° C., 6 h) to obtain an oily substance.
  • This oily substance was put into a three-necked flask, 672 ml of chloroform and 21.8 ml of methanesulfonic acid were added, and the mixture was refluxed for 3 hours in a nitrogen atmosphere. The mixture was cooled to room temperature, then carefully neutralized with an aqueous sodium hydrogen carbonate solution, and extracted with dichloromethane using a separatory funnel. The extract was dried over anhydrous magnesium sulfate, filtered through a silica gel pad, and concentrated.
  • This concentrate was recrystallized with a mixed solvent of toluene and hexane (5:10 ml / g). As a result, the target intermediate 2a was obtained in a yield of 27.9 g and a yield of 50%.
  • the resulting filtrate was filtered through a silica gel pad and concentrated.
  • the concentrate obtained by concentrating the obtained fraction was recrystallized from hexane (5 ml / g, 5 ° C.). As a result, the target product Intermediate 3a was obtained in a yield of 19.68 g and a yield of 61%.
  • 2-Bromo-1,3,5-triisopropylbenzene (43.9 g, 155 mmol) and dehydrated tetrahydrofuran 155 ml were placed in a three-necked flask and cooled to -78 ° C.
  • a 1.60 M hexane solution of n-butyllithium (106.6 ml, 170.5 mmol) was added with a syringe and stirred at ⁇ 78 ° C. for 10 minutes, and then trimethoxyborane (34.5 ml, 310 mmol) was added for 2 minutes. It was dripped over. The mixture was then stirred at ⁇ 78 ° C. for 30 minutes and then at room temperature overnight.
  • the mixture was concentrated to about half by an evaporator, 300 ml of 1N hydrochloric acid aqueous solution was added, and the mixture was stirred at room temperature for 4 hours.
  • the resulting solution was placed in a separatory funnel and extracted with dichloromethane.
  • the extract was washed twice with water, dried over anhydrous magnesium sulfate, filtered and concentrated.
  • This concentrate was put into a three-necked flask equipped with a Soxhlet extractor charged with molecular sieves, and 200 ml of toluene and 30 ml of methanol were added and refluxed for 12 hours. After completion of the reaction, the mixture was cooled to room temperature and concentrated with an evaporator.
  • the solvent of the obtained fraction was removed by vacuum drying, and the target colorless oily substance (intermediate 3c) was obtained in a yield of 31.88 g and a yield of 74%.
  • 1,4-dibromo-2-fluorobenzene 50.78 g, 200 mmol
  • potassium hydroxide (6.73 g, 120 mmol)
  • potassium carbonate 27.64 g, 200 mmol
  • 20 ml of triethylene glycol dimethyl ether 20 ml
  • the mixture was heated and stirred at 180 ° C. for 96 hours in a nitrogen atmosphere.
  • the mixture was cooled to room temperature, diluted by adding 500 ml of toluene, and further subjected to sonication for 10 minutes by adding 500 ml of water.
  • the mixture was filtered using celite, and the filtrate was collected.
  • the filtrate was transferred to a separatory funnel and washed twice with water to recover the organic phase.
  • the obtained organic phase was dried over anhydrous magnesium sulfate, filtered through a silica gel pad, and concentrated.
  • the intermediate product 4a was obtained in a yield of 8.51 g and a yield of 18%.
  • the obtained organic phase was dried over anhydrous magnesium sulfate, filtered through a silica gel pad, and concentrated.
  • This white solid was rinsed with hexane and then vacuum-dried to obtain 9.40 g of the target intermediate 5a in a yield of 88%.
  • 2,5-dibromofluorobenzene (15.23 g, 60 mmol), 2-bromobenzenethiol (9.45 g, 50 mmol), potassium carbonate (13.82 g, 100 mmol), and 10 ml of triethylene glycol dimethyl ether were placed in a three-necked flask, and nitrogen was added. The mixture was heated and stirred at 180 ° C. for 24 hours in an atmosphere. After completion of the reaction, the mixture was cooled to room temperature, diluted with 100 ml of toluene, and further sonicated with 100 ml of water for 10 minutes. The mixture was filtered using celite, and the filtrate was collected.
  • reaction solution was deactivated by adding a small amount of water, and extracted with dichloromethane using a separatory funnel.
  • the obtained extract was dried over anhydrous magnesium sulfate, filtered, and concentrated to obtain a reaction crude product.
  • This crude reaction product was placed in a three-necked flask, 600 ml of chloroform and 3.9 ml of methanesulfonic acid were added, and the mixture was refluxed for 3 hours in a nitrogen atmosphere.
  • the mixture was cooled to room temperature and washed with water using a separatory funnel.
  • the washed mixture was dried over anhydrous magnesium sulfate, filtered through a silica gel pad, and concentrated to obtain a precipitate.
  • This precipitate was recrystallized with ethanol to obtain 10.2 g of a target intermediate 8b in a yield of 45%.
  • the resulting solution was washed with a separatory funnel, and then residual bromine was deactivated with a sodium thiosulfate / sodium hydroxide aqueous solution.
  • the solution was dried over anhydrous magnesium sulfate, filtered through a silica gel pad, and concentrated.
  • the obtained concentrate was purified by silica gel chromatography using hexane as a developing solvent.
  • the resulting fraction concentrate was recrystallized from hexane.
  • the target intermediate 11a was obtained in a yield of 38.29 g and a yield of 79%.
  • Intermediate 11b was synthesized in the same manner as Compound 5 Synthesis Method A described later, except that Intermediate 11a (14.57 g, 30 mmol) was used as a raw material. The obtained intermediate 11b was 6.27 g in yield and 39% in yield.
  • 2,4,6-Triphenylbromobenzene (25.5 g, 66 mmol) and 264 ml of dehydrated tetrahydrofuran were placed in a three-necked flask, cooled to ⁇ 80 ° C., and 1.60 M hexane solution (45. 4 ml, 72.6 mmol) was added via syringe. Thereafter, the reaction solution was stirred at ⁇ 80 ° C. for 15 minutes, and then trimethoxyborane (14.7 ml, 132 mmol) was added by syringe and stirred overnight at room temperature.
  • the resulting solution was filtered through a silica gel pad and the filtrate was concentrated.
  • the concentrate of the obtained fraction was recrystallized with hexane to obtain 2.20 g of the target compound 5 in a yield of 37%.
  • the resulting solution was filtered using celite and concentrated.
  • Synthesis Example 11 Synthesis of Compound 176
  • Compound 176 was synthesized in the same manner as the compound 59 synthesis method, except that intermediate 7b (2.16 mmol) and intermediate 2a (2.59 mmol) were used as raw materials.
  • the compound 176 obtained was 0.85 g in yield and 54% in yield.
  • an organic photoluminescence element and an organic electroluminescence element were produced and evaluated. Emission characteristics are evaluated by source meter (Keithley: 2400 series), semiconductor parameter analyzer (Agilent Technology: E5273A), optical power meter measuring device (Newport: 1930C), optical spectrometer (Ocean) Optics: USB2000), a spectroradiometer (Topcon: SR-3) and a streak camera (Hamamatsu Photonics C4334) were used.
  • Singlet energy E S1 A sample having a thickness of 100 nm was prepared on a Si substrate by co-evaporating the measurement target compound and mCP so that the measurement target compound had a concentration of 6% by weight. The fluorescence spectrum of this sample was measured at room temperature (300K). By integrating the luminescence from immediately after the excitation light incidence to 100 nanoseconds after the incidence, a fluorescence spectrum having a luminescence intensity on the vertical axis and a wavelength on the horizontal axis was obtained.
  • the vertical axis represents light emission and the horizontal axis represents wavelength.
  • a tangent line was drawn with respect to the short-wave rise of the emission spectrum, and the wavelength value ⁇ edge [nm] at the intersection of the tangent line and the horizontal axis was obtained.
  • a value obtained by converting this wavelength value into an energy value by the following conversion formula was defined as E S1 .
  • Conversion formula: E S1 [eV] 1239.85 / ⁇ edge
  • the maximum point having a peak intensity of 10% or less of the maximum peak intensity of the spectrum is not included in the above-mentioned maximum value on the shortest wavelength side, and has the maximum slope value closest to the maximum value on the shortest wavelength side.
  • the tangent drawn at the point where the value was taken was taken as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side.
  • Example 1 Preparation and Evaluation of Organic Photoluminescence Device Using Compound 5
  • a toluene solution (concentration 10 ⁇ 5 mol / L) and a hexane solution (concentration 10 ⁇ 5 mol / L) of compound 5 were prepared in the atmosphere. Then, after deoxygenation by bubbling with nitrogen for 15 minutes, it was used for measurement of light emission characteristics.
  • a thin film of compound 5 was formed to a thickness of 100 nm on a quartz substrate by a vacuum deposition method under a vacuum degree of 10 ⁇ 4 Pa or less to obtain an organic photoluminescence device.
  • the result of measuring the emission spectrum of the toluene solution and the hexane solution of Compound 5 is shown in FIG.
  • the photoluminescence quantum yield ⁇ was 0.97 for the toluene solution, 0.54 for the hexane solution, and 0.83 for the organic photoluminescence device having a thin film of Compound 5.
  • Energy difference Delta] E ST of the singlet excited state and a triplet excited state as determined from the fluorescence spectrum and phosphorescence spectrum was 0.05 eV.
  • the transient decay curve of the toluene solution of compound 5 and a hexane solution is shown in FIG.
  • This transient decay curve shows the result of measuring the luminescence lifetime obtained by measuring the process in which the emission intensity is deactivated by applying excitation light to the compound.
  • the light emission intensity decays in a single exponential manner. This means that if the vertical axis of the graph is semi-log, it will decay linearly.
  • the transient decay curve of Compound 5 shown in FIG. 4 such a linear component (fluorescence) is observed at the beginning of observation, but a component deviating from linearity appears after several ⁇ sec. This is light emission of the delay component, and the signal added to the initial component becomes a loose curve with a tail on the long time side.
  • Compound 5 is a luminescent material containing a delay component in addition to the fluorescent component.
  • the emission lifetime ⁇ 1 of the immediate fluorescence component in the toluene solution is 35 ns
  • the emission lifetime ⁇ 2 of the delayed fluorescence component is 1.35 ⁇ s
  • the emission lifetime ⁇ 1 of the immediate fluorescence component in the hexane solution is 21 ns
  • the emission lifetime ⁇ 2 of the delay fluorescence component is 2.09 ⁇ s.
  • Example 2 Production and evaluation of organic photoluminescence device using compound 6
  • a toluene solution and a hexane solution of compound 6 by the same method as in Example 1, An organic photoluminescence device having a thin film of Compound 6 was produced. Further, a thin film in which the concentration of compound 6 is 6.0% by weight is deposited on a quartz substrate by a vacuum deposition method under the condition of a vacuum degree of 10 ⁇ 4 Pa or less from different deposition sources. An organic photoluminescence device was formed with a thickness of 100 nm.
  • FIG. 5 shows the results of measuring the emission spectrum of an organic photoluminescence device having a toluene solution and a hexane solution of compound 6 and a thin film of compound 6 and mCP. The results are shown in FIG.
  • the photoluminescence quantum yield ⁇ was 1.00 for the toluene solution, 0.54 for the hexane solution, and 0.88 for the organic photoluminescence device having a thin film of compound 6 alone.
  • Energy difference Delta] E ST of the singlet excited state and a triplet excited state as determined from the fluorescence spectrum and phosphorescence spectrum was 0.08 eV.
  • the transient decay curve of the toluene solution of compound 6 and a hexane solution is shown in FIG.
  • the emission lifetime ⁇ 1 of the immediate fluorescence component in the toluene solution is 33 ns
  • the emission lifetime ⁇ 2 of the delayed fluorescence component is 1.60 ⁇ s
  • the emission lifetime ⁇ 1 of the immediate fluorescence component in the hexane solution is 20 ns
  • the emission lifetime ⁇ 2 of the delay fluorescence component is 1.29 ⁇ s.
  • Example 3 Preparation and Evaluation of Organic Photoluminescence Device Using Compound 18
  • a toluene solution of Compound 18 was prepared in the same manner as in Example 1 except that Compound 18 was used instead of Compound 5.
  • the emission spectrum and transient decay curve of this toluene solution were measured.
  • the measured emission spectrum is shown in FIG. 8, and the transient decay curve is shown in FIG.
  • the photoluminescence quantum yield ⁇ of the toluene solution of compound 18 was 0.81.
  • the emission lifetime ⁇ 1 of the immediate fluorescence component was 89.3 ns
  • the emission lifetime ⁇ 2 of the delayed fluorescence component was 39.5 ⁇ s.
  • Example 4 Production and Evaluation of Organic Photoluminescence Device Using Compound 59
  • a toluene solution of compound 59 was prepared in the same manner as in Example 1, except that compound 59 was used instead of compound 5.
  • the emission spectrum and transient decay curve of this toluene solution were measured.
  • the measured emission spectrum is shown in FIG.
  • the photoluminescence quantum yield ⁇ of the toluene solution of compound 59 was 0.76. Further, the emission lifetime ⁇ 1 of the immediate fluorescence component was 27.7 ns, and the emission lifetime ⁇ 2 of the delayed fluorescence component was 4.02 ⁇ s.
  • Example 5 Production and Evaluation of Organic Photoluminescence Device Using Compound 65
  • a toluene solution of compound 65 was prepared by the same method as in Example 1 except that compound 65 was used instead of compound 5.
  • the emission spectrum and transient decay curve of this toluene solution were measured.
  • the measured emission spectrum is shown in FIG.
  • the photoluminescence quantum yield ⁇ of the toluene solution of compound 65 was 0.56. Further, the emission lifetime ⁇ 1 of the immediate fluorescence component was 25.9 ns, and the emission lifetime ⁇ 2 of the delayed fluorescence component was 2.06 ⁇ s.
  • Example 6 Production and Evaluation of Organic Photoluminescence Device Using Compound 67
  • a toluene solution of compound 67 was prepared in the same manner as in Example 1 except that compound 67 was used instead of compound 5.
  • the emission spectrum and transient decay curve of this toluene solution were measured.
  • the measured emission spectrum is shown in FIG.
  • the photoluminescence quantum yield ⁇ of the toluene solution of compound 67 was 1.00. Further, the emission lifetime ⁇ 1 of the immediate fluorescence component was 35 ns, and the emission lifetime ⁇ 2 of the delayed fluorescence component was 2.33 ⁇ s.
  • Example 7 Production and Evaluation of Organic Photoluminescence Device Using Compound 156
  • a toluene solution of compound 156 was prepared in the same manner as in Example 1 except that compound 156 was used instead of compound 5.
  • the emission spectrum and transient decay curve of this toluene solution were measured.
  • the measured emission spectrum is shown in FIG. 13, and the transient decay curve is shown in FIG.
  • the photoluminescence quantum yield ⁇ of the toluene solution of compound 156 was 1.00.
  • the emission lifetime ⁇ 1 of the immediate fluorescence component was 3.2 ns
  • the emission lifetime ⁇ 2 of the delayed fluorescence component was 1.61 ⁇ s.
  • Example 8 A toluene solution was prepared in the same manner as in Example 1, except that the compounds 88, 116, and 176 were used instead of the compound 5. The emission spectrum and transient decay curve of this toluene solution were measured. Table 1 shows the photoluminescence quantum yield ⁇ and the emission lifetime determined from the measured emission spectrum and transient decay curve. As shown in Table 1, all the toluene solutions of the compounds 88, 116, and 176 obtained a sufficient photoluminescence quantum yield ⁇ , and confirmed delayed fluorescence.
  • Comparative Example 1 Preparation and Evaluation of Organic Photoluminescence Device Using Comparative Compound A Using Comparative Compound A having the following structure instead of Compound 1, a toluene solution of Comparative Compound A was prepared in the same manner as Example 1. Prepared. The emission spectrum and transient decay curve of this toluene solution were measured. The measured emission spectrum is shown in FIG. 15, and the transient decay curve is shown in FIG. The emission lifetime was 16.0 ns, and no delayed fluorescence was observed.
  • Comparative Example 2 Preparation and Evaluation of Organic Photoluminescence Element Using Comparative Compound B Using Comparative Compound B having the following structure instead of Compound 1, a toluene solution of Comparative Compound A was prepared in the same manner as Example 1. Prepared. The emission spectrum and transient decay curve of this toluene solution were measured. The measured emission spectrum is shown in FIG. 17, and the transient decay curve is shown in FIG. The photoluminescence quantum yield ⁇ of the toluene solution of Comparative Compound B was 0.27. Moreover, the light emission lifetime was 8.1 ns, and no delayed fluorescence was observed.
  • Comparative Example 3 Preparation and Evaluation of Organic Photoluminescence Device Using Comparative Compound C having the following structure instead of Compound 1, a toluene solution of Comparative Compound C was prepared in the same manner as Example 1. Prepared. The emission spectrum and transient decay curve of this toluene solution were measured. The measured emission spectrum is shown in FIG. 19, and the transient decay curve is shown in FIG. The photoluminescence quantum yield ⁇ of the toluene solution of Comparative Compound C was 0.26. The emission lifetime was 12.7 ns, and no delayed fluorescence was observed.
  • Example 11 Production and evaluation of organic electroluminescence device using compound 5 Each thin film was formed by vacuum deposition on a glass substrate on which an anode made of indium tin oxide (ITO) having a thickness of 100 nm was formed. And a degree of vacuum of 5.0 ⁇ 10 ⁇ 4 Pa or less. First, ⁇ -NPD was formed on ITO with a thickness of 30 nm, and mCP was formed thereon with a thickness of 10 nm. Next, Compound 5 and (Cz) 2 DBF were co-evaporated from different vapor deposition sources to form a layer having a thickness of 15 nm as a light emitting layer. At this time, the concentration of Compound 5 was 6.0% by weight.
  • ITO indium tin oxide
  • PPT was formed to a thickness of 10 nm, and TPBi was formed thereon to a thickness of 40 nm. Further, lithium fluoride (LiF) was vacuum-deposited at 0.8 nm, and then aluminum (Al) was evaporated at a thickness of 100 nm to form a cathode, thereby obtaining an organic electroluminescence device.
  • LiF lithium fluoride
  • Al aluminum
  • the emission spectrum of the produced organic electroluminescence device is shown in FIG. 21, and the current density-external quantum efficiency characteristic is shown in FIG.
  • the organic electroluminescence device using Compound 5 as the light emitting material achieved a high external quantum efficiency of 15.3%.
  • Example 12 Production and evaluation of organic electroluminescence device using compound 6 An organic electroluminescence device was produced in the same manner as in Example 4 using compound 6 instead of compound 5. The emission spectrum of the produced organic electroluminescence element is shown in FIG. 23, and the current density-external quantum efficiency characteristic is shown in FIG. The organic electroluminescence device using Compound 5 as the light emitting material achieved a high external quantum efficiency of 8.9%.
  • the compound of the present invention is useful as a luminescent material. For this reason, the compound of this invention is effectively used as a luminescent material for organic light emitting elements, such as an organic electroluminescent element. Since the compounds of the present invention include those that emit delayed fluorescence, it is also possible to provide an organic light-emitting device with high luminous efficiency. For this reason, this invention has high industrial applicability.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Inorganic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

Cette invention concerne un composé représenté par la formule générale (1) qui est utile à titre de matériau électroluminescent. R1 à R8 représentent indépendamment un atome d'hydrogène ou un substituant, et R9 représente un substituant, au moins un des R1 à R8 désignant un groupe représenté par la formule générale (2) ou autre. L12 représente une liaison simple ou un groupe de liaison bivalent, et * représente un site de liaison à un cycle benzène dans la formule générale (1). R11 à R20 représentent indépendamment un atome d'hydrogène ou un substituant.
PCT/JP2014/080162 2013-11-18 2014-11-14 Matériau électroluminescent, élément électroluminescent organique, et composé WO2015072537A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2015547802A JP6392240B2 (ja) 2013-11-18 2014-11-14 発光材料、有機発光素子および化合物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2013237824 2013-11-18
JP2013-237824 2013-11-18

Publications (1)

Publication Number Publication Date
WO2015072537A1 true WO2015072537A1 (fr) 2015-05-21

Family

ID=53057471

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2014/080162 WO2015072537A1 (fr) 2013-11-18 2014-11-14 Matériau électroluminescent, élément électroluminescent organique, et composé

Country Status (3)

Country Link
JP (1) JP6392240B2 (fr)
TW (1) TW201527485A (fr)
WO (1) WO2015072537A1 (fr)

Cited By (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2017126606A (ja) * 2016-01-12 2017-07-20 コニカミノルタ株式会社 電子デバイス材料、有機エレクトロルミネッセンス素子、表示装置、及び、照明装置
WO2018159662A1 (fr) * 2017-02-28 2018-09-07 国立大学法人九州大学 Composé, matériau électroluminescent et élément électroluminescent organique
WO2018212169A1 (fr) * 2017-05-16 2018-11-22 学校法人関西学院 Composé aromatique polycyclique
US10333085B2 (en) 2016-07-13 2019-06-25 Samsung Display Co., Ltd. Polycyclic compound and organic electroluminescence device including the same
WO2019131079A1 (fr) * 2017-12-25 2019-07-04 学校法人関西学院 Composé contenant du bore en tant qu'atome spiro et composé macromoléculaire associé
EP3508490A1 (fr) * 2018-01-08 2019-07-10 Samsung Display Co., Ltd. Dispositif électroluminescent organique et composé polycyclique pour dispositif électroluminescent organique
CN110272440A (zh) * 2018-03-15 2019-09-24 江苏三月光电科技有限公司 一种含硼六元杂环化合物及其在有机电致发光器件中的应用
WO2020076796A1 (fr) 2018-10-09 2020-04-16 Kyulux, Inc. Nouvelle composition de matière destinée à être utilisée dans des diodes électroluminescentes organiques
CN111662311A (zh) * 2019-03-05 2020-09-15 三星显示有限公司 有机电致发光器件和用于有机电致发光器件的多环化合物
CN112661778A (zh) * 2020-12-30 2021-04-16 中节能万润股份有限公司 一种含硼的芳基酰亚胺类有机电致发光材料及其应用
WO2021157642A1 (fr) 2020-02-04 2021-08-12 株式会社Ｋｙｕｌｕｘ Matériau hôte, composition, et élément luminescent organique
US11101440B2 (en) 2015-07-01 2021-08-24 Kyushu University, National University Corporation Organic electroluminescent device
WO2021235549A1 (fr) 2020-05-22 2021-11-25 株式会社Kyulux Composé, matériau électroluminescent et élément électroluminescent
WO2022009883A1 (fr) 2020-07-08 2022-01-13 日鉄ケミカル＆マテリアル株式会社 Matériau à fluorescence retardée activée par la chaleur et élément électroluminescent organique
WO2022025248A1 (fr) 2020-07-31 2022-02-03 株式会社Kyulux Composé, matériau luminescent, et élément luminescent
US11335872B2 (en) 2016-09-06 2022-05-17 Kyulux, Inc. Organic light-emitting device
JP2022077011A (ja) * 2020-11-10 2022-05-20 エルジー ディスプレイ カンパニー リミテッド 有機発光ダイオードおよび有機発光装置
WO2022168956A1 (fr) 2021-02-04 2022-08-11 株式会社Kyulux Composé, matériau électroluminescent et élément électroluminescent organique
US11462690B2 (en) 2018-11-29 2022-10-04 Samsung Display Co., Ltd. Organic electroluminescence device and polycyclic compound for organic electroluminescence device
US11476435B2 (en) 2017-08-24 2022-10-18 Kyushu University, National University Corporation Film and organic light-emitting device containing perovskite-type compound and organic light-emitting material
US11482679B2 (en) 2017-05-23 2022-10-25 Kyushu University, National University Corporation Compound, light-emitting lifetime lengthening agent, use of n-type compound, film and light-emitting device
WO2022244503A1 (fr) 2021-05-20 2022-11-24 株式会社Kyulux Elément électroluminescent organique
WO2022270354A1 (fr) 2021-06-23 2022-12-29 株式会社Kyulux Composé, matériau électroluminescent et élément électroluminescent organique
WO2022270602A1 (fr) 2021-06-23 2022-12-29 株式会社Kyulux Élément électroluminescent organique et film
WO2022270113A1 (fr) 2021-06-23 2022-12-29 株式会社Kyulux Élément électroluminescent organique
WO2023282224A1 (fr) 2021-07-06 2023-01-12 株式会社Kyulux Élément émetteur de lumière organique et son procédé de conception
WO2023053835A1 (fr) 2021-09-28 2023-04-06 株式会社Kyulux Composé, composition, matériau hôte, matériau barrière aux électrons et élément électroluminescent organique
US11634438B2 (en) 2018-04-12 2023-04-25 Samsung Display Co., Ltd. Heterocyclic compound and organic light-emitting device including the same
US11785837B2 (en) 2019-11-08 2023-10-10 Samsung Display Co., Ltd. Organic electroluminescence device and polycyclic compound for organic electroluminescence device
US11930654B2 (en) 2017-07-06 2024-03-12 Kyulux, Inc. Organic light-emitting element
US11950492B2 (en) 2019-01-29 2024-04-02 Samsung Display Co., Ltd. Organic electroluminescence device and polycyclic compound for organic electroluminescence device

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019062684A1 (fr) * 2017-09-29 2019-04-04 江苏三月光电科技有限公司 Composé organique contenant du bore et son application dans un dispositif électroluminescent organique
CN109575056A (zh) * 2017-09-29 2019-04-05 江苏三月光电科技有限公司 一种含硼有机化合物及其在有机电致发光器件中的应用
CN113980054B (zh) * 2021-11-18 2023-12-15 广东工业大学 一种含膦氧化合物及其制备和应用

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013526548A (ja) * 2010-05-14 2013-06-24 ユニバーサル ディスプレイ コーポレイション Ｐｈｏｌｅｄのためのホスト材料およびドーパントとしてのアザボリン化合物

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013526548A (ja) * 2010-05-14 2013-06-24 ユニバーサル ディスプレイ コーポレイション Ｐｈｏｌｅｄのためのホスト材料およびドーパントとしてのアザボリン化合物

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
A. K. C. MENGEL ET AL.: "A Triarylamine- Triarylborane Dyad with a Photochromic Dithienylethene Bridge", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 77, 16 July 2012 (2012-07-16), pages 6545 - 6552 *
J. KOBAYASHI ET AL.: "Synthesis of Dibenzochalcogenaborins and Systematic Comparisons of Their Optical Properties by Changing a Bridging Chalcogen Atom", CHEMISTRY - AN ASIAN JOURNAL, vol. 4, 19 November 2008 (2008-11-19), pages 42 - 49 *
P. CHEN ET AL.: "n-Expanded Borazine: An Ambipolar Conjugated B-n-N Macrocycle", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 51, 5 July 2012 (2012-07-05), pages 7994 - 7998 *
T. AGOU ET AL.: "Development of a general route to periphery-functionalized azaborines and ladder-type azaborines by using common intermediates", CHEMICAL COMMUNICATIONS, pages 3204 - 3206 *

Cited By (45)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11101440B2 (en) 2015-07-01 2021-08-24 Kyushu University, National University Corporation Organic electroluminescent device
JP2017126606A (ja) * 2016-01-12 2017-07-20 コニカミノルタ株式会社 電子デバイス材料、有機エレクトロルミネッセンス素子、表示装置、及び、照明装置
US10333085B2 (en) 2016-07-13 2019-06-25 Samsung Display Co., Ltd. Polycyclic compound and organic electroluminescence device including the same
US11335872B2 (en) 2016-09-06 2022-05-17 Kyulux, Inc. Organic light-emitting device
CN110520421A (zh) * 2017-02-28 2019-11-29 国立大学法人九州大学 化合物、发光材料及有机发光元件
WO2018159662A1 (fr) * 2017-02-28 2018-09-07 国立大学法人九州大学 Composé, matériau électroluminescent et élément électroluminescent organique
JPWO2018212169A1 (ja) * 2017-05-16 2020-03-19 学校法人関西学院 多環芳香族化合物
CN110612304A (zh) * 2017-05-16 2019-12-24 学校法人关西学院 多环芳香族化合物
JP7202572B2 (ja) 2017-05-16 2023-01-12 学校法人関西学院 多環芳香族化合物
WO2018212169A1 (fr) * 2017-05-16 2018-11-22 学校法人関西学院 Composé aromatique polycyclique
US11482679B2 (en) 2017-05-23 2022-10-25 Kyushu University, National University Corporation Compound, light-emitting lifetime lengthening agent, use of n-type compound, film and light-emitting device
US11930654B2 (en) 2017-07-06 2024-03-12 Kyulux, Inc. Organic light-emitting element
US11476435B2 (en) 2017-08-24 2022-10-18 Kyushu University, National University Corporation Film and organic light-emitting device containing perovskite-type compound and organic light-emitting material
CN111527094A (zh) * 2017-12-25 2020-08-11 学校法人关西学院 具有硼作为螺原子的化合物及其高分子化合物
KR102674465B1 (ko) 2017-12-25 2024-06-11 가꼬우 호징 관세이 가쿠잉 붕소를 스피로 원자로 한 화합물 및 그의 고분자 화합물
JPWO2019131079A1 (ja) * 2017-12-25 2021-01-28 学校法人関西学院 ホウ素をスピロ原子とした化合物およびその高分子化合物
JP7341412B2 (ja) 2017-12-25 2023-09-11 学校法人関西学院 ホウ素をスピロ原子とした化合物およびその高分子化合物
CN111527094B (zh) * 2017-12-25 2024-03-26 学校法人关西学院 化合物及其高分子化合物、有机元件用材料、有机电致发光元件、显示装置及照明装置
KR20200101969A (ko) 2017-12-25 2020-08-28 가꼬우 호징 관세이 가쿠잉 붕소를 스피로 원자로 한 화합물 및 그의 고분자 화합물
WO2019131079A1 (fr) * 2017-12-25 2019-07-04 学校法人関西学院 Composé contenant du bore en tant qu'atome spiro et composé macromoléculaire associé
EP3508490A1 (fr) * 2018-01-08 2019-07-10 Samsung Display Co., Ltd. Dispositif électroluminescent organique et composé polycyclique pour dispositif électroluminescent organique
US11251380B2 (en) 2018-01-08 2022-02-15 Samsung Display Co., Ltd. Organic electroluminescence device and polycyclic compound for organic electroluminescence device
CN110272440A (zh) * 2018-03-15 2019-09-24 江苏三月光电科技有限公司 一种含硼六元杂环化合物及其在有机电致发光器件中的应用
US11634438B2 (en) 2018-04-12 2023-04-25 Samsung Display Co., Ltd. Heterocyclic compound and organic light-emitting device including the same
WO2020076796A1 (fr) 2018-10-09 2020-04-16 Kyulux, Inc. Nouvelle composition de matière destinée à être utilisée dans des diodes électroluminescentes organiques
US11462690B2 (en) 2018-11-29 2022-10-04 Samsung Display Co., Ltd. Organic electroluminescence device and polycyclic compound for organic electroluminescence device
US11950492B2 (en) 2019-01-29 2024-04-02 Samsung Display Co., Ltd. Organic electroluminescence device and polycyclic compound for organic electroluminescence device
CN111662311A (zh) * 2019-03-05 2020-09-15 三星显示有限公司 有机电致发光器件和用于有机电致发光器件的多环化合物
US11785837B2 (en) 2019-11-08 2023-10-10 Samsung Display Co., Ltd. Organic electroluminescence device and polycyclic compound for organic electroluminescence device
WO2021157593A1 (fr) 2020-02-04 2021-08-12 株式会社Ｋｙｕｌｕｘ Composition, film, élément électroluminescent organique, procédé de fourniture de composition électroluminescente, et programme
WO2021157642A1 (fr) 2020-02-04 2021-08-12 株式会社Ｋｙｕｌｕｘ Matériau hôte, composition, et élément luminescent organique
WO2021235549A1 (fr) 2020-05-22 2021-11-25 株式会社Kyulux Composé, matériau électroluminescent et élément électroluminescent
KR20230035528A (ko) 2020-07-08 2023-03-14 닛테츠 케미컬 앤드 머티리얼 가부시키가이샤 열활성화 지연 형광재료, 및 유기 전계 발광소자
WO2022009883A1 (fr) 2020-07-08 2022-01-13 日鉄ケミカル＆マテリアル株式会社 Matériau à fluorescence retardée activée par la chaleur et élément électroluminescent organique
WO2022025248A1 (fr) 2020-07-31 2022-02-03 株式会社Kyulux Composé, matériau luminescent, et élément luminescent
JP7246453B2 (ja) 2020-11-10 2023-03-27 エルジー ディスプレイ カンパニー リミテッド 有機発光ダイオードおよび有機発光装置
JP2022077011A (ja) * 2020-11-10 2022-05-20 エルジー ディスプレイ カンパニー リミテッド 有機発光ダイオードおよび有機発光装置
CN112661778A (zh) * 2020-12-30 2021-04-16 中节能万润股份有限公司 一种含硼的芳基酰亚胺类有机电致发光材料及其应用
WO2022168956A1 (fr) 2021-02-04 2022-08-11 株式会社Kyulux Composé, matériau électroluminescent et élément électroluminescent organique
WO2022244503A1 (fr) 2021-05-20 2022-11-24 株式会社Kyulux Elément électroluminescent organique
WO2022270113A1 (fr) 2021-06-23 2022-12-29 株式会社Kyulux Élément électroluminescent organique
WO2022270602A1 (fr) 2021-06-23 2022-12-29 株式会社Kyulux Élément électroluminescent organique et film
WO2022270354A1 (fr) 2021-06-23 2022-12-29 株式会社Kyulux Composé, matériau électroluminescent et élément électroluminescent organique
WO2023282224A1 (fr) 2021-07-06 2023-01-12 株式会社Kyulux Élément émetteur de lumière organique et son procédé de conception
WO2023053835A1 (fr) 2021-09-28 2023-04-06 株式会社Kyulux Composé, composition, matériau hôte, matériau barrière aux électrons et élément électroluminescent organique

Also Published As

Publication number Publication date
TW201527485A (zh) 2015-07-16
JP6392240B2 (ja) 2018-09-19
JPWO2015072537A1 (ja) 2017-03-16

Similar Documents

Publication Publication Date Title
JP6392240B2 (ja) 発光材料、有機発光素子および化合物
JP6318155B2 (ja) 化合物、発光材料および有機発光素子
WO2015080182A1 (fr) Matériau électroluminescent, élément organique électroluminescent et composé
JP6430370B2 (ja) 発光材料、有機発光素子および化合物
JP6284370B2 (ja) 発光材料、有機発光素子および化合物
JP6466913B2 (ja) 発光材料、有機発光素子および化合物
WO2015080183A1 (fr) Substance électroluminescente, élément électroluminescent organique, et composé
JP6225111B2 (ja) 発光材料、化合物、およびそれらを用いた有機発光素子
JP6293417B2 (ja) 化合物、発光材料および有機発光素子
JP6472383B2 (ja) 発光材料、並びに、これを用いた遅延蛍光体および有機発光素子
JP6367189B2 (ja) 発光材料、有機発光素子および化合物
JP6326050B2 (ja) 化合物、発光材料および有機発光素子
JP6383538B2 (ja) 発光材料、有機発光素子および化合物
WO2015002213A1 (fr) Matériau électroluminescent, substance fluorescente de longue durée, élément électroluminescent organique et composé
WO2015129715A1 (fr) Substance luminescente, élément organique luminescent et composé associé
WO2015133501A1 (fr) Matériau électroluminescent, élément organique électroluminescent et composé
WO2014133121A1 (fr) Composé, matériau électroluminescent, et élément électroluminescent organique
WO2015129714A1 (fr) Matériau électroluminescent, élément électroluminescent organique, et composé
JP6647514B2 (ja) 有機発光素子ならびにそれに用いる発光材料および化合物
JPWO2013161437A1 (ja) 発光材料および有機発光素子
WO2019004254A1 (fr) Matériau électroluminescent, composé, phosphore à longue persistance et élément électroluminescent
JP2019006988A (ja) 発光材料、化合物、遅延蛍光体および発光素子
WO2018043241A1 (fr) Élément électroluminescent organique, matériau luminescent et composé utilisé à cet effet
JP6622484B2 (ja) 発光材料、有機発光素子および化合物
WO2016111196A1 (fr) Composé, mélange, couche photo-émettrice, élément électroluminescent organique, et dopant auxiliaire

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 14862491

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2015547802

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 14862491

Country of ref document: EP

Kind code of ref document: A1