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WO2017115834A1 - Composé, matériau électroluminescent et élément électroluminescent organique - Google Patents

Composé, matériau électroluminescent et élément électroluminescent organique Download PDF

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Publication number
WO2017115834A1
WO2017115834A1 PCT/JP2016/089033 JP2016089033W WO2017115834A1 WO 2017115834 A1 WO2017115834 A1 WO 2017115834A1 JP 2016089033 W JP2016089033 W JP 2016089033W WO 2017115834 A1 WO2017115834 A1 WO 2017115834A1
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Prior art keywords
group
substituted
unsubstituted
compound
carbazolyl
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PCT/JP2016/089033
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English (en)
Japanese (ja)
Inventor
圭朗 那須
安達　千波矢
一 中野谷
洸子 野村
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Kyushu University NUC
Kyulux Inc
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Kyushu University NUC
Kyulux Inc
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Priority claimed from JP2016079892A external-priority patent/JP6829547B2/ja
Application filed by Kyushu University NUC, Kyulux Inc filed Critical Kyushu University NUC
Priority to US16/066,814 priority Critical patent/US11038118B2/en
Priority to CN201680076802.8A priority patent/CN108473424B/zh
Publication of WO2017115834A1 publication Critical patent/WO2017115834A1/fr
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

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.
  • Some of these studies focus on compounds that emit delayed fluorescence. Delayed fluorescence is emitted when a compound that has been excited by energy donation undergoes reverse intersystem crossing from the excited triplet state to the excited singlet state and then returns to the ground state from the excited singlet state. This is fluorescence, which is observed after the fluorescence from the directly excited singlet state (normal fluorescence).
  • Patent Document 1 describes that a compound in which two cyano groups and one or more carbazolyl groups are substituted on a benzene ring is a compound that can emit delayed fluorescence. And when these compounds are used as luminescent materials, such as an organic electroluminescent element, it is described that luminous efficiency can be improved.
  • the present inventors have found that among compounds having a structure in which only one cyano group is substituted on the benzene ring, there are compounds that can emit delayed fluorescence. And it came to the knowledge that an organic light emitting element with high luminous efficiency can be provided by using the compound which can radiate
  • the present invention has been proposed based on such knowledge, and specifically has the following configuration.
  • a compound having a structure represented by the following general formula (1) [In the general formula (1), three or more of R 1 , R 2 , R 4 and R 5 are each independently a substituted or unsubstituted 9-carbazolyl group, a substituted or unsubstituted 10-phenoxazyl group, It represents a substituted or unsubstituted 10-phenothiazyl group or a cyano group. The remainder represents a hydrogen atom or a substituent, which is not a substituted or unsubstituted 9-carbazolyl group, a substituted or unsubstituted 10-phenoxazyl group, or a substituted or unsubstituted 10-phenothiazyl group.
  • R 3 each independently represents a hydrogen atom or a substituent, and the substituent is a substituted or unsubstituted 9-carbazolyl group, a substituted or unsubstituted 10-phenoxazyl group, a cyano group, a substituted or unsubstituted 10 -It is not a phenothiazyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkynyl group.
  • R 1 , R 2 , R 4 and R 5 are substituted or unsubstituted branched alkyl groups, substituted or unsubstituted alkoxy groups, and substituted or unsubstituted diarylamino groups
  • Three or more of R 1 , R 2 , R 4 and R 5 are 9-carbazolyl groups substituted with one or more substituted or unsubstituted branched alkyl groups [ [1] or [2].
  • R 1 , R 2 , R 4 and R 5 are 9-carbazolyl groups substituted at the 3-position and 6-position with substituents [1] to [3] The compound of any one of these.
  • R 3 is a hydrogen atom.
  • a luminescent material comprising the compound according to any one of [1] to [8].
  • the light-emitting material according to [9] which emits delayed fluorescence.
  • An organic light emitting device having a light emitting layer containing the light emitting material according to [9] or [10] on a substrate.
  • the organic light-emitting device according to [11] which is an organic electroluminescence device.
  • the organic light-emitting device according to [11] or [12], wherein the light-emitting layer contains the compound according to any one of [1] to [8] and a host material.
  • three or more of R 1 ′, R 2 ′, R 4 ′ and R 5 ′ are each independently a substituted or unsubstituted 9-carbazolyl group, substituted or unsubstituted 10 -Represents a phenoxazyl group or a substituted or unsubstituted 10-phenothiazyl group.
  • the rest represents a hydrogen atom or a substituent, which is a substituted or unsubstituted 9-carbazolyl group, a substituted or unsubstituted 10-phenoxazyl group, a substituted or unsubstituted 10-phenothiazyl group, or a cyano group is not.
  • One or more carbon atoms constituting each ring skeleton of the 9-carbazolyl group, the 10-phenoxazyl group, and the 10-phenothiazyl group may be substituted with a nitrogen atom.
  • R 3 ′ each independently represents a hydrogen atom or a substituent, which may be a substituted or unsubstituted 9-carbazolyl group, a substituted or unsubstituted 10-phenoxazyl group, a substituted or unsubstituted 10-phenothiazyl group. Or a cyano group.
  • the compound of the present invention is useful as a light emitting material.
  • the compound of the present invention can emit delayed fluorescence, and its excited triplet energy can be effectively used for light emission. For this reason, the organic light emitting element using the compound of the present invention as a light emitting material can realize high luminous efficiency.
  • FIG. It is the emission spectrum and absorption spectrum of the toluene solution of the compound 1 of Example 1.
  • 2 is a transient decay curve of a toluene solution of Compound 1 of Example 1.
  • FIG. It is the emission spectrum and absorption spectrum of the toluene solution of the compound 2 of Example 2.
  • 3 is a transient decay curve of a toluene solution of Compound 2 of Example 2.
  • 4 is a transient decay curve of a toluene solution of compound 3 of Example 3.
  • 2 is an emission spectrum of a toluene solution of compound 814 in Example 4.
  • 4 is a transient decay curve of a toluene solution of the compound 814 in Example 4.
  • 2 shows an emission spectrum and an absorption spectrum of a toluene solution of compound 816 in Example 5.
  • 6 is a transient decay curve of a toluene solution of the compound 816 of Example 5.
  • 3 is a transient decay curve of a toluene solution of Comparative Compound 1.
  • 3 is a transient decay curve of a toluene solution of Comparative Compound 2.
  • 3 is a transient decay curve of a toluene solution of Comparative Compound 3.
  • 2 is an emission spectrum of an organic electroluminescence device using Compound 1.
  • 4 is a graph showing luminance-external quantum efficiency characteristics of an organic electroluminescence device using Compound 1.
  • 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 containing a compound represented by the following general formula (1).
  • R 1 , R 2 , R 4 and R 5 are each independently a substituted or unsubstituted 9-carbazolyl group, a substituted or unsubstituted 10-phenoxazyl group, or It represents a substituted or unsubstituted 10-phenothiazyl group.
  • the rest represents a hydrogen atom or a substituent, which is a substituted or unsubstituted 9-carbazolyl group, a substituted or unsubstituted 10-phenoxazyl group, a substituted or unsubstituted 10-phenothiazyl group, or a cyano group. Absent.
  • R 1 , R 2 , R 4 and R 5 those which are a substituted or unsubstituted 9-carbazolyl group, a substituted or unsubstituted 10-phenoxazyl group, or a substituted or unsubstituted 10-phenothiazyl group are 3 There may be four or four, but preferably four.
  • R 1 , R 2 , R 4 and R 5 are a substituted or unsubstituted 9-carbazolyl group, a substituted or unsubstituted 10-phenoxazyl group, or a substituted or unsubstituted 10-phenothiazyl group
  • R 1 , R 2 and R 4 , or R 1 , R 2 and R 5 may be R 1 , R 2 and R 4 , or R 1 , R 2 and R 5 .
  • R 1 , R 2 , R 4 and R 5 those which are a substituted or unsubstituted 9-carbazolyl group, a substituted or unsubstituted 10-phenoxazyl group, or a substituted or unsubstituted 10-phenothiazyl group are the same These structures may be different structures or different structures, but the same structure is preferable.
  • R 1, R 2, R 4 and R 5 is preferably at least one of which is a substituted or unsubstituted 9-carbazolyl group, or three of which are substituted or unsubstituted 9-carbazolyl group, That is, all of R 1 , R 2 , R 4 and R 5 are substituted or unsubstituted 9-carbazolyl groups, or three of R 1 , R 2 , R 4 and R 5 are substituted or unsubstituted. It is more preferably a substituted 9-carbazolyl group.
  • R 1 , R 2 , R 4 and R 5 are substituted or unsubstituted branched alkyl groups, substituted or unsubstituted alkoxy groups, and substituted or unsubstituted diarylamino groups.
  • the unsubstituted branched alkyl group preferably has 3 to 10 carbon atoms, and more preferably 3 to 5 carbon atoms.
  • the substitution position is not particularly limited. Preferred examples include those in which at least one of the 3-position and the 6-position is substituted, and more preferably those in which both the 3-position and the 6-position are substituted.
  • one or more carbon atoms constituting each ring skeleton may be substituted with a nitrogen atom.
  • the number of carbon atoms substituted with a nitrogen atom is not particularly limited, but is preferably 1 to 4, more preferably 1 or 2.
  • R 3 represents a hydrogen atom or a substituent, and the substituent includes a substituted or unsubstituted 9-carbazolyl group, a substituted or unsubstituted 10-phenoxazyl group, a substituted or unsubstituted 10-phenothiazyl group, a cyano group, It is not a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or a substituted or unsubstituted alkynyl group.
  • R 3 is preferably a hydrogen atom.
  • R 1 , R 2 , R 4 , and R 5 are each a 10-phenoxazyl group or 10-phenothiazyl group substituted with a substituent
  • the substituent of the 10-phenoxazyl group or 10-phenothiazyl group is, for example, a hydroxy group Halogen atom, cyano group, alkyl group having 1 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms, alkylthio group having 1 to 20 carbon atoms, alkyl-substituted amino group having 1 to 20 carbon atoms, 2 to 20 carbon atoms Acyl group, aryl group having 6 to 40 carbon atoms, heteroaryl group having 3 to 40 carbon atoms, alkenyl group having 2 to 10 carbon atoms, alkynyl group having 2 to 10 carbon atoms, alkoxycarbonyl group having 2 to 10 carbon atoms An alkylsulfonyl group having 1 to 10 carbon atoms, a hal
  • 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 2 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 2 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.
  • R 1 , R 2 , R 4 and R 5 are a substituted or unsubstituted 9-carbazolyl group, a substituted or unsubstituted 10-phenoxazyl group, or a substituted or unsubstituted 10-phenothiazyl group
  • substituents that can be taken by the remaining R 1 , R 2 , R 4 or R 5 include those other than the cyano group among those exemplified as the substituent of the 10-phenoxazyl group or 10-phenothiazyl group.
  • the heteroaryl group does not include a substituted or unsubstituted 9-carbazolyl group, a substituted or unsubstituted 10-phenoxazyl group, or a substituted or unsubstituted 10-phenothiazyl group. More preferred substituents are a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, and a substituted or unsubstituted aryl group having 6 to 40 carbon atoms.
  • examples of the substituent R 3 can be taken, the above 10-phenoxazyl group, a substituted 10-out of the illustrated ones as the substituent of phenothiazyl group, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, having a carbon number of 3 to Examples include those other than 40-substituted or unsubstituted heteroaryl groups, alkynyl groups having 2 to 10 carbon atoms, trialkylsilylalkynyl groups having 5 to 20 carbon atoms, and cyano groups.
  • More preferable substituents are a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, and a dialkyl-substituted amino group having 2 to 20 carbon atoms.
  • the dialkylamino group may be formed by linking alkyl groups with an oxygen atom or the like to form a ring structure.
  • 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.
  • the compound represented by the general formula (1) is a novel compound.
  • the compound represented by the general formula (1) can be synthesized by combining known reactions.
  • R 1 , R 2 , R 4 and R 5 in the general formula (1) are substituted or unsubstituted 9-carbazolyl groups, substituted or unsubstituted 10-phenoxazyl groups, or substituted or unsubstituted 10-phenothiazyl groups.
  • R 11 to R 14 and R 17 to R 20 each independently represents a hydrogen atom or a substituent.
  • L represents a single bond, an oxygen atom or a sulfur atom.
  • X represents a halogen atom, and examples thereof include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a fluorine atom, a bromine atom and an iodine atom are preferable.
  • the above reaction is an application of a known coupling 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 delayed phosphor of the present invention has a structure represented by the following general formula (1 ′).
  • general formula (1 ′) three or more of R 1 ′, R 2 ′, R 4 ′ and R 5 ′ are each independently a substituted or unsubstituted 9-carbazolyl group, substituted or unsubstituted 10 -Represents a phenoxazyl group or a substituted or unsubstituted 10-phenothiazyl group.
  • the rest represents a hydrogen atom or a substituent, which is a substituted or unsubstituted 9-carbazolyl group, a substituted or unsubstituted 10-phenoxazyl group, a substituted or unsubstituted 10-phenothiazyl group, or a cyano group. Absent. One or more carbon atoms constituting each ring skeleton of the 9-carbazolyl group, the 10-phenoxazyl group, and the 10-phenothiazyl group may be substituted with a nitrogen atom.
  • R 3 each independently represents a hydrogen atom or a substituent, and the substituent is a substituted or unsubstituted 9-carbazolyl group, a substituted or unsubstituted 10-phenoxazyl group, a substituted or unsubstituted 10-phenothiazyl group. Or a cyano group.
  • R 1 ′ to R 5 ′ see the explanations, preferred ranges and specific examples of R 1 to R 5 in the compound represented by the general formula (1). Can do.
  • Examples of the substituent that R 3 ′ can take include, in addition to the substituent that R 3 can take, a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, and a substituted or unsubstituted group having 3 to 40 carbon atoms.
  • Heteroaryl groups excluding substituted or unsubstituted 9-carbazolyl groups, substituted or unsubstituted 10-phenoxazyl groups, substituted or unsubstituted 10-phenothiazyl groups
  • alkynyl groups having 2 to 10 carbon atoms, 5 carbon atoms Mention may also be made of ⁇ 20 trialkylsilylalkynyl groups.
  • a compound containing a plurality of structures represented by the general formula (1) in the molecule as a light emitting material. It is also conceivable to use a compound containing a plurality of structures represented by the general formula (1 ′) as a delayed phosphor.
  • a polymer obtained by preliminarily allowing a polymerizable group to be present in the structure represented by the general formula (1) or the general formula (1 ′) and polymerizing the polymerizable group is used as a luminescent material or It can be considered to be used as a delayed phosphor.
  • a monomer containing a polymerizable functional group is prepared in any one of R 1 to R 5 in the general formula (1) or R 1 ′ to R 5 ′ in the general formula (1 ′). It is conceivable that a polymer having a repeating unit is obtained by polymerizing it alone or copolymerizing with other monomers, and the polymer is used as a light emitting material or a delayed phosphor. Alternatively, it is also conceivable that dimers and trimers are obtained by coupling compounds having a structure represented by the general formula (1) and used as a light emitting material or a delayed phosphor.
  • a polymer having a repeating unit containing a structure represented by the general formula (1) or the general formula (1 ′) a polymer containing a structure represented by the following general formula (11) or (12) be able to.
  • Q represents a group including a structure represented by General Formula (1) or General Formula (1 ′), and 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 5 in the structure of the general formula (1) constituting Q and any of R 1 ′ to R 5 ′ in the general formula (1 ′). Can be combined. Two or more linking groups may be linked to one Q to form a crosslinked structure or a network structure.
  • the polymer having a repeating unit containing the formulas (13) to (16) is any one of R 1 to R 5 having the structure of the general formula (1) or R 1 ′ having the structure of the general formula (1 ′).
  • ⁇ advance by introducing hydroxy groups into R 5 ', which was introduced a polymerizable group by reacting the following compound as a linker, may be synthesized by polymerizing the polymerizable group.
  • the polymer containing a structure represented by the general formula (1) or general formula (1 ′) in the molecule is composed only of a repeating unit having a structure represented by the general formula (1) or general formula (1 ′).
  • a polymer may be sufficient and the polymer containing the repeating unit which has another structure may be sufficient.
  • the repeating unit having a structure represented by the general formula (1) or 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) or 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.
  • 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. Moreover, you may use the compound represented by General formula (1) of this invention as a host or an assist dopant.
  • 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.
  • 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 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. In FIG. 1, 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, and 7 is a cathode. Below, each member and each layer of an organic electroluminescent element are demonstrated. In addition, description of a 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.
  • 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.
  • 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.
  • 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, thiopyran dioxide oxide 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 one organic layer (for example, an electron transport layer) but also for a plurality of organic layers. .
  • the compound represented by General formula (1) used for each organic layer may be the same as or different from each other.
  • the injection layer, the blocking layer, the hole blocking layer, the electron blocking layer, the exciton blocking layer, the hole transport layer, and the like are also represented by the general formula (1).
  • a compound may be used.
  • 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, R ′, and R 1 to R 10 each independently represent a hydrogen atom or a substituent.
  • X represents a carbon atom or a hetero atom forming a ring skeleton
  • n represents an integer of 3 to 5
  • Y represents a substituent
  • m represents an integer of 0 or more.
  • the organic electroluminescence 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, the thermal deactivation rate constant is large, and the luminescence rate constant is small. Therefore, it is hardly observable at room temperature.
  • the excited triplet energy of a normal organic compound it can be measured by observing light emission under extremely low temperature conditions.
  • the organic light emitting device of the present invention at least one layer of the organic layer contains the compound represented by the general formula (1) of the present invention, so that electrons and holes are smoothly transported to the light emitting layer and the light emitting material.
  • the above-described light emission can be efficiently generated.
  • deterioration of characteristics due to high temperatures and deterioration of characteristics over time during driving can be suppressed, and high thermal stability and a long element lifetime can be obtained.
  • 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.
  • the UV absorption spectrum was measured using UV-2550 (manufactured by Shimadzu Corporation) or LAMBDA950-PKA (manufactured by PerkinElmer), and the emission spectrum was measured using Fluoromax-4 (manufactured by HORIBA Jobin Yvon).
  • the transient attenuation curve was measured using Quantaurus-tau (manufactured by Hamamatsu Photonics). In this example, fluorescence having a light emission lifetime of 0.05 ⁇ s or more was determined as delayed fluorescence.
  • Example 1 Preparation and Evaluation of Organic Photoluminescence Device Using Compound 1
  • a toluene solution of Compound 1 (concentration 1 ⁇ 10 ⁇ 5 mol / L) was prepared in a glove box under an Ar atmosphere.
  • FIG. 2 shows an emission spectrum and an absorption spectrum of the toluene solution of Compound 1 measured using 300 nm excitation light
  • FIG. 3 shows a transient decay curve measured using 340 nm excitation light after bubbling with argon.
  • a solid line represents an emission spectrum
  • a dotted line represents an absorption spectrum.
  • the photoluminescence quantum efficiency was 12.0% in the toluene solution before bubbling and 45.4% in the toluene solution after bubbling with argon. Further, from FIG.
  • a fluorescent component having a fast decay and a delayed fluorescent component having a slow decay are confirmed.
  • the light emission lifetime of the fluorescent component having a fast decay is 1.65 ns (nanosecond), and the light emission lifetime of the delayed fluorescent component is 70 ⁇ s. there were. From these results, it was confirmed that Compound 1 is a compound capable of emitting delayed fluorescence and has high luminous efficiency.
  • Example 2 Compound 2 was used in place Preparation and Evaluation Compound 1 of the organic photoluminescent device using the compound 2, the toluene solution under the same conditions as in Example 1 (concentration 1 ⁇ 10 -5 mol / L) Prepared.
  • FIG. 4 shows an emission spectrum and an absorption spectrum of the toluene solution of Compound 2 measured using 337 nm excitation light
  • FIG. 5 shows a transient decay curve measured using 340 nm excitation light after bubbling with argon.
  • a solid line represents an emission spectrum
  • a dotted line represents an absorption spectrum.
  • the photoluminescence quantum efficiency was 10.0% in the toluene solution before bubbling and 13.7% in the toluene solution after bubbling with argon. Further, from FIG. 5, a fluorescent component having a fast decay and a delayed fluorescent component having a slow decay were confirmed. The light emission lifetime of the fluorescent component having a fast decay was 2.8 ns, and the light emission lifetime of the delayed fluorescent component was 17 ⁇ s. From these results, it was confirmed that the compound 2 is a compound capable of emitting delayed fluorescence and has high luminous efficiency.
  • Example 3 Preparation and Evaluation of Organic Photoluminescence Device Using Compound 3
  • a compound 3 was used instead of compound 1, and a toluene solution (concentration 1 ⁇ 10 ⁇ 5 mol / L) was prepared under the same conditions as in Example 1.
  • FIG. 6 shows an emission spectrum and an absorption spectrum of a toluene solution of Compound 3 measured using 337 nm excitation light
  • FIG. 7 shows a transient attenuation curve measured using 340 nm excitation light after bubbling with argon.
  • a solid line represents an emission spectrum
  • a dotted line represents an absorption spectrum.
  • the photoluminescence quantum efficiency was 17.8% in the toluene solution before bubbling and 21.0% in the toluene solution after bubbling with argon. Further, from FIG. 7, a fluorescent component having a fast decay and a delayed fluorescent component having a slow decay were confirmed. The light emission lifetime of the fluorescent component having a fast decay was 6.6 ns, and the light emission lifetime of the delayed fluorescence component was 96 ⁇ s. From these results, it was confirmed that the compound 3 is a compound capable of emitting delayed fluorescence and has high luminous efficiency.
  • Example 4 Preparation and evaluation of organic photoluminescence device using compound 814
  • Compound 814 was used instead of compound 1, and a toluene solution (concentration 1 ⁇ 10 -5 mol / L) was prepared under the same conditions as in Example 1.
  • FIG. 8 shows an emission spectrum of a toluene solution of compound 814 measured using 337 nm excitation light
  • FIG. 9 shows a transient decay curve measured using 340 nm excitation light after bubbling with argon.
  • the photoluminescence quantum efficiency was 27.4% in the toluene solution before bubbling, and 37.4% in the toluene solution after bubbling with argon. Further, from FIG.
  • Example 5 Preparation and Evaluation of Organic Photoluminescence Device Using Compound 816
  • Compound 816 was used in place of Compound 1, and a toluene solution (concentration 1 ⁇ 10 ⁇ 5 mol / L) was prepared under the same conditions as in Example 1.
  • FIG. 10 shows an emission spectrum and an absorption spectrum of a toluene solution of Compound 816 measured using 337 nm excitation light
  • FIG. 11 shows a transient attenuation curve measured using 340 nm excitation light after bubbling with argon.
  • a solid line represents an emission spectrum and a dotted line represents an absorption spectrum.
  • the photoluminescence quantum efficiency was 13.1% in the toluene solution before bubbling, and 39.4% in the toluene solution after bubbling with argon.
  • a fluorescent component having a fast decay and a delayed fluorescent component having a slow decay were confirmed, the light emission lifetime of the fluorescent component having a fast decay was 2.2 ns, and the light emission lifetime of the delayed fluorescence component was 6.3 ⁇ s. . From these results, it was confirmed that the compound 816 was a compound capable of emitting delayed fluorescence and had high luminous efficiency.
  • Comparative Example 1 Preparation and Evaluation of Organic Photoluminescence Device Using Comparative Compound 1
  • comparative compound 1 represented by the following formula was used, and a toluene solution (concentration 1 ⁇ ) under the same conditions as in Example 1. the 10 -5 mol / L) was prepared.
  • FIG. 12 shows the transient decay curve of the toluene solution of Comparative Compound 1 measured using 280 nm excitation light after bubbling with argon.
  • the photoluminescence quantum efficiency was 17.0% in the toluene solution before bubbling, and 35.1% in the toluene solution after bubbling with argon. From FIG. 12, no delayed fluorescent component was confirmed, and only a fluorescent component having a fast decay (luminescence lifetime: 10.9 ns) was observed.
  • Comparative Example 2 Preparation and Evaluation of Organic Photoluminescence Device Using Comparative Compound 2
  • a toluene solution (concentration 1 ⁇ ) was used under the same conditions as in Example 1, except that Comparative Compound 2 represented by the following formula was used instead of Compound 1. 10 ⁇ 5 mol / L) was prepared.
  • FIG. 13 shows a transient decay curve of a toluene solution of Comparative Compound 2 measured using 280 nm excitation light after bubbling with argon.
  • the photoluminescence quantum efficiency was 14.4% in the toluene solution before bubbling and 18.9% in the toluene solution after bubbling with argon. From FIG. 13, no delayed fluorescent component was confirmed, and only a fluorescent component with a fast decay (luminescence lifetime: 3.75 ns) was observed.
  • Comparative Example 3 Preparation and Evaluation of Organic Photoluminescence Device Using Comparative Compound 1
  • a comparative compound 3 represented by the following formula was used, and a toluene solution (concentration 1 ⁇ ) under the same conditions as in Example 1. 10 ⁇ 5 mol / L) was prepared.
  • FIG. 14 shows the transient decay curve of the toluene solution of Comparative Compound 3 measured using 280 nm excitation light after bubbling with argon.
  • the photoluminescence quantum efficiency was 8.60% in the toluene solution before bubbling and 10.7% in the toluene solution after bubbling with argon. From FIG. 14, no delayed fluorescent component was confirmed, and only a fluorescent component with a fast decay (luminescence lifetime: 3.94 ns) was observed.
  • Example 6 Preparation and Evaluation of Organic Electroluminescent Device Using Compound 1
  • ITO indium tin oxide
  • HAT-CN was formed on ITO to a thickness of 10 nm
  • TAPC was formed thereon to a thickness of 30 nm
  • mCP was formed thereon to a thickness of 10 nm.
  • Compound 1 and PPT were co-deposited from different vapor deposition sources to form a layer having a thickness of 30 nm to form a light emitting layer. At this time, the concentration of Compound 1 was 15% by weight.
  • FIG. 16 shows luminance vs. external quantum efficiency characteristics. It was confirmed that an external quantum efficiency of 20% was achieved.
  • 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.

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Abstract

L'invention concerne un composé présentant une structure représentée par la formule générale suivante qui émet une fluorescence retardée et est utile comme matériau électroluminescent. Trois, ou plus, parmi R1, R2, R4 et R5 représentent un groupe 9-carbazolyle, 10-phénoxazyle ou 10-phénothiazyle. Le reste et R3 représentent des atomes d'hydrogène ou d'autres substituants, mais ne sont pas des groupes cyano. En plus, R3 n'est pas un groupe aryle, un groupe hétéroaryle ou un groupe alcynyle.
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