WO2018123783A1 - 有機電界発光素子用材料及び有機電界発光素子 - Google Patents

有機電界発光素子用材料及び有機電界発光素子 Download PDF

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WO2018123783A1
WO2018123783A1 PCT/JP2017/045847 JP2017045847W WO2018123783A1 WO 2018123783 A1 WO2018123783 A1 WO 2018123783A1 JP 2017045847 W JP2017045847 W JP 2017045847W WO 2018123783 A1 WO2018123783 A1 WO 2018123783A1
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carbon atoms
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organic
compound
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PCT/JP2017/045847
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French (fr)
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裕士 池永
林　健太郎
拓男 長浜
川田　敦志
敬之 福松
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新日鉄住金化学株式会社
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Priority to KR1020197016846A priority Critical patent/KR102498770B1/ko
Priority to KR1020237004439A priority patent/KR102628129B1/ko
Priority to JP2018559108A priority patent/JPWO2018123783A1/ja
Publication of WO2018123783A1 publication Critical patent/WO2018123783A1/ja
Priority to JP2024022776A priority patent/JP2024052784A/ja

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • 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
    • 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
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • 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]

Definitions

  • the present invention relates to an organic electroluminescent element material, an organic electroluminescent element film, and an organic electroluminescent element (hereinafter referred to as an organic EL element). Specifically, a compound having a conformation number within a specific range is used. The present invention relates to an organic EL element material.
  • Patent Document 1 discloses an organic EL element using a TTF (Triplet-Triplet Fusion) mechanism, which is one of delayed fluorescence mechanisms.
  • TTF Triplet-Triplet Fusion
  • the TTF mechanism uses the phenomenon that singlet excitons are generated by collision of two triplet excitons, and it is theoretically thought that the internal quantum efficiency can be increased to 40%.
  • Patent Document 2 discloses an organic EL element using a TADF (Thermally Activated Delayed Fluorescence) mechanism.
  • the TADF mechanism utilizes the phenomenon that reverse intersystem crossing from triplet excitons to singlet excitons occurs in materials where the energy difference between singlet and triplet levels is small. It is thought to be raised to 100%. However, there is a demand for further improvement in the life characteristics as in the phosphorescent light emitting device.
  • Patent Document 3 discloses the use of an indolocarbazole compound as a host material.
  • Patent Document 4 discloses the use of an indolocarbazole compound as a mixed host.
  • Patent Document 5 discloses the use of a host material in which a plurality of hosts containing an indolocarbazole compound are premixed. However, none of them are sufficient, and further improvements are desired. In addition, there is no teaching that a compound having a conformational number within a specific range is used as a material for an organic electroluminescence device.
  • An object of this invention is to provide the practically useful organic EL element which has high efficiency and high drive stability in view of the said present condition, and a compound suitable for it.
  • the present invention is represented by the general formula (1), has a skeleton structure in which an aromatic hydrocarbon group and / or an aromatic heterocyclic group are linked, and the skeleton structure not containing a substituent has a molecular weight of 500 or more and 1500 or less.
  • a compound for an organic electroluminescence device characterized in that the number of conformations generated by conformational search calculation of the skeleton structure is 9 to 100,000.
  • Ar is independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 24 carbon atoms, or 2 of these aromatic rings.
  • -10 represents a substituted or unsubstituted linked aromatic group formed by linking.
  • HetAr represents a substituted or unsubstituted aromatic heterocyclic group having 3 to 24 carbon atoms.
  • z represents an integer of 2 to 5.
  • n is an integer obtained by subtracting 4 from the total number of Ar 2 to Ar 7 .
  • ring A represents an aromatic ring represented by the formula (A2) condensed at an arbitrary position of two adjacent rings.
  • Ring B represents a nitrogen-containing five-membered ring represented by the formula (B2) that is fused at any position of two adjacent rings.
  • L is a substituted or unsubstituted aromatic group or a linked aromatic group independently represented by the formula (c2), Ar 1 to Ar 7 are each independently Ar 1 , Ar 3 and Ar 5 are divalent Ar 2 is i + 1 valent, Ar 4 is h + 1 valent, Ar 6 is g + 1 valent, Ar 7 is a monovalent aromatic hydrocarbon group having 6 to 24 carbon atoms, or aromatic group having 3 to 16 carbon atoms.
  • a heterocyclic group, and these aromatic hydrocarbon groups or aromatic heterocyclic groups may each independently have a substituent Q, and in the case of having a substituent, the substituent Q is deuterium, halogen, Cyano group, nitro group, alkyl group having 1 to 20 carbon atoms, aralkyl group having 7 to 38 carbon atoms, alkenyl group having 2 to 20 carbon atoms, alkynyl group having 2 to 20 carbon atoms, dialkylamino having 2 to 40 carbon atoms A diarylamino group having 12 to 44 carbon atoms, a diaralkylamino group having 14 to 76 carbon atoms, an acyl group having 2 to 20 carbon atoms, an acyloxy group having 2 to 20 carbon atoms, and an aryl group having 1 to 20 carbon atoms.
  • a group substituted with R 1 to R 3 each independently represent a substituent Q or L. At least one of L has a total number of Ar 2 to Ar 7 of 4 or more.
  • a, b, and c represent the number of substitutions, and each independently represents an integer of 0 to 2.
  • d, e, and f represent the number of repetitions, and each independently represents an integer of 0 to 5.
  • g, h, and i represent the number of substitutions, and each independently represents an integer of 0 to 5.
  • the total number of Ar 1 to Ar 7 contained in all L in the general formula (2) is preferably 6 or more and 10 or less.
  • ring C represents an aromatic ring represented by the formula (C3) that is condensed at an arbitrary position of two adjacent rings.
  • Ring D represents a nitrogen-containing five-membered ring represented by the formula (D3) that is fused at any position of two adjacent rings.
  • L is in agreement with the general formula (2), and Ar 2 in at least one L represents an i + 1-valent substituted or unsubstituted aromatic heterocyclic group having 3 to 9 carbon atoms.
  • L in the general formula (3) may be a group represented by the following formula (c5).
  • Ar 1 , Ar 3 to Ar 7 , d to i are the same as in formula (c2)
  • X represents CH, C— or nitrogen independently, and at least one of X represents nitrogen.
  • i in L is 2 to 4, and the i substituents may be different from each other.
  • any of Ar 2 to Ar 7 in L can have at least one partial structure represented by the formula (4). Preferably, it can have two or more.
  • any one of L is a group L 2 represented by the formula (c2) other than the formula (c5), and any one of Ar 2 to Ar 7 in the L 2 , It is preferable to have at least one partial structure represented by the formula (4).
  • any one of Ar 2 to Ar 7 in L preferably has at least one partial structure represented by the formula (5).
  • Ar 1 and Ar 3 to Ar 7 in L are preferably an aromatic hydrocarbon group having 6 carbon atoms.
  • at least one of L is the formula (c5), and Ar 3 to Ar 7 in the formula (c5) have at least one partial structure represented by the formula (5) Can do.
  • a preferred embodiment of the present invention is shown below.
  • the above-mentioned compound for organic electroluminescence device having a solubility in toluene at 40 ° C. of 1% or more.
  • Another embodiment is a material for an organic electroluminescence device comprising at least one of the above compounds for organic electroluminescence device.
  • Another aspect is an organic electroluminescent element including an organic layer made of the above-described organic electroluminescent element material.
  • Another aspect is a composition for an organic electroluminescent element obtained by dissolving or dispersing the above-described organic electroluminescent element material in a solvent.
  • Another aspect is an organic electroluminescent device comprising an organic layer comprising a coating film of the composition for organic electroluminescent devices.
  • the organic layer may be at least one layer selected from a light emitting layer, a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer, and preferably emits light. Is a layer.
  • the light emitting layer can contain a light emitting dopant material.
  • the material for organic electroluminescent elements of the present invention contains the compound for organic electroluminescent elements of the present invention.
  • This compound has a structure in which a plurality of aromatic rings including an aromatic heterocycle are connected, and can take various three-dimensional conformations, so that it is crystalline compared to a material having a structure with few conformations.
  • a film having high amorphous stability can be formed.
  • the material for organic electroluminescence device of the present invention When the compound for organic electroluminescence device of the present invention is a compound having an indolocarbazole skeleton, the material for organic electroluminescence device has high stability in the active state of oxidation, reduction and exciton and has high heat resistance Thus, an organic electroluminescent element using an organic thin film formed therefrom exhibits high luminous efficiency and driving stability.
  • the material for an organic electroluminescent element of the present invention is a mixture containing at least one compound for an organic electroluminescent element of the present invention, the mixture is used for the same organic electroluminescent element layer, whereby holes in the layer are formed. And the carrier balance of electrons can be adjusted, and a higher performance organic EL device can be realized.
  • the organic electroluminescent element material of the present invention can have various three-dimensional structures as described above, packing between molecules is weak and solubility in an organic solvent is high. This material is therefore adaptable to the application process.
  • the compound for an organic electroluminescence device of the present invention has a molecular weight of 500 to 1500 in a skeleton structure only linked to an aromatic hydrocarbon group and an aromatic heterocyclic group not containing a substituent, and conformational search of the skeleton structure It has a structure in which the number of conformations generated by calculation is 9 to 100,000, and is represented by the above general formula (1).
  • the compound for an organic electroluminescent device of the present invention has a skeletal structure in which an aromatic ring of an aromatic group selected from an aromatic hydrocarbon group and an aromatic heterocyclic group is connected by a direct bond, such as an alkyl group.
  • the skeleton structure may be linear or branched.
  • the molecular weight of the above skeleton structure alone is 500 to 1500, but if the molecular weight is too low, the amorphous stability of the material may be lowered. If the molecular weight is too high, the heating temperature required for vapor deposition film formation Increases and the possibility of material degradation increases. Therefore, the molecular weight range is 500 to 1500, preferably 600 to 1300, more preferably 700 to 1100.
  • the compound for organic electroluminescence device of the present invention has a skeleton structure in which the number of conformations generated by conformational search calculation is 9 to 100,000. If the number of conformations is too small, the amorphous stability of the material may be reduced. In addition, when the number of conformations is too large, the volume fraction of the structure related to charge transport and light emission decreases, so that charge transport characteristics and light emission characteristics deteriorate, and an excellent organic electroluminescence device cannot be obtained. Therefore, the range of the conformational number of the skeleton structure possessed by the compound for organic charge light emitting device of the present invention is 9 to 100,000, preferably 12 to 50,000, more preferably 15 to 20,000.
  • the conformation indicates a local stable structure that can be taken by the bond rotation and bond direction of the molecule, and the multiple conformations generated by the conformational search calculation are in a conformational relationship with each other. is there.
  • Conformational search can be easily calculated by executing a molecular force field calculation using software such as CONFLEX (manufactured by Conflex) or MacroModel (manufactured by Schrodinger). it can. Preferred specific calculation methods are described in the examples.
  • CONFLEX manufactured by Conflex
  • MacroModel manufactured by Schrodinger
  • Ar is independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 3 to 24 carbon atoms, or these A substituted or unsubstituted linked aromatic group formed by connecting 2 to 10 aromatic rings.
  • Ar examples include benzene, pentalene, indene, naphthalene, azulene, heptalene, octalene, indacene, acenaphthylene, phenalene, phenanthrene, anthracene, tridene, fluoranthene, acephenanthrylene, acanthrylene, triphenylene, pyrene, chrysene, Tetraphen, tetracene, pleiaden, picene, perylene, pentaphen, pentacene, tetraphenylene, cholanthrylene, helicene, hexaphene, rubicene, coronene, trinaphthylene, heptaphene, pyranthrene, furan, benzofuran, isobenzofuran, xanthene, oxatolene, dibenzofuran, perixane Tenox
  • HetAr represents a substituted or unsubstituted aromatic heterocyclic group having 3 to 24 carbon atoms.
  • Specific examples thereof include furan, benzofuran, isobenzofuran, xanthene, oxatolene, dibenzofuran, perixanthenoxanthene, thiophene, thioxanthene, thianthrene, phenoxathiin, thionaphthene, isothianaphthene, thiophene, thiophanthrene, dibenzothiophene, Pyrrole, pyrazole, tellurazole, selenazole, thiazole, isothiazole, oxazole, furazane, pyridine, pyrazine, pyrimidine, pyridazine, triazine, indolizine, indole, isoindole, indazole, purine, quinolidine, is
  • Preferred is a group formed by removing hydrogen from pyridine, pyrazine, pyrimidine, pyridazine, triazine, carbazole, indole, indoloindole, indolocarbazole, dibenzofuran, dibenzothiophene, quinoline, isoquinoline, quinoxaline, quinazoline or naphthyridine.
  • the number of hydrogen removed is z.
  • z represents an integer of 2 to 5, and is more preferably an integer of 2 to 4 from the viewpoint of amorphous stability and charge transport characteristics.
  • Preferred examples of the compound for organic electroluminescence device of the present invention include compounds represented by the above general formula (2) or general formula (3).
  • the ring A represents an aromatic ring represented by the formula (A2) that is condensed at an arbitrary position of two adjacent rings.
  • Ring B represents a nitrogen-containing five-membered ring represented by the formula (B2) that is fused at any position of two adjacent rings.
  • L is independently represented by the formula (c2).
  • Ar 1 to Ar 7 each independently represents an aromatic hydrocarbon group having 6 to 24 carbon atoms or an aromatic heterocyclic group having 3 to 16 carbon atoms, and these aromatic hydrocarbon group or aromatic heterocyclic group Each may be independently substituted, in which case the substituent Q is deuterium, halogen, cyano group, nitro group, alkyl group having 1 to 20 carbon atoms, aralkyl group having 7 to 38 carbon atoms, carbon number 2 to 20 alkenyl groups, 2 to 20 alkynyl groups, 2 to 40 dialkylamino groups, 12 to 44 diarylamino groups, 14 to 76 diaralkylamino groups, 2 carbon atoms ⁇ 20 acyl group, C2-C20 acyloxy group, C1-C20 alkoxy group, C2-C20 alkoxycarbonyl group, C2-C20 alkoxycarbonyloxy group, C1-C20 Or a hydrogen atom in these hydrocarbon groups is deuterium Or an been substituted with halogen.
  • R 1 to R 3 each independently represent the above substituent Q or L.
  • L may be 2 or more, but at least one of them has a total number of Ar 2 to Ar 7 contained in L of 4 or more.
  • a, b, and c represent the number of substitutions, and each independently represents an integer of 0 to 2.
  • d, e, and f represent the number of repetitions, and each independently represents an integer of 0 to 5.
  • g, h, and i represent the number of substitutions, and each independently represents an integer of 0 to 5.
  • the total number of Ar 2 to Ar 7 can be calculated from the number of e, f, g, h, and i in the formula (c2).
  • the number of conformations generated by conformational search calculation is preferably greater than 4 ⁇ 2 n and not greater than 4 ⁇ 4 n + 1 , more preferably Is greater than 4 ⁇ 2 n and less than or equal to 4 ⁇ 4 n , more preferably greater than 4 ⁇ 2 n + 1 and less than or equal to 4 ⁇ 4 n .
  • n is an integer obtained by subtracting 4 from the total number of Ar 2 to Ar 7. At this time, n is preferably 1 to 7, and more preferably 2 to 5.
  • the total number of the Ar 2 ⁇ Ar 7 are the general formula (2), since L is two or more, is understood to be the sum of the total number of Ar 2 ⁇ Ar 7 for each L.
  • Ar 1 to Ar 7 represent an aromatic hydrocarbon group having 6 to 24 carbon atoms or an aromatic heterocyclic group having 3 to 16 carbon atoms. Specific examples thereof include benzene, Pentalene, indene, naphthalene, azulene, heptalene, octalene, indacene, acenaphthylene, phenalene, phenanthrene, anthracene, triindene, fluoranthene, acephenanthrylene, acanthrylene, triphenylene, pyrene, chrysene, tetraphene, tetracene, preaden, picene , Perylene, pentaphen, pentacene, tetraphenylene, cholanthrylene, helicene, hexaphene, rubicene, coronene, trinaphthylene, heptaphene, pyranthren
  • a, b and c represent the number of substitutions and each independently represents an integer of 0 to 2, but preferably represents an integer of 0 to 1.
  • d, e, and f represent the number of repetitions, and each independently represents an integer of 0 to 5, preferably an integer of 0 to 4, more preferably an integer of 0 to 3.
  • g, h, and i represent the number of substitutions, and each independently represents an integer of 0 to 5, preferably an integer of 0 to 4, more preferably an integer of 0 to 2.
  • either d or i is preferably an integer of 1 or more.
  • the ring C represents an aromatic ring represented by the formula (C3) that is condensed at an arbitrary position of two adjacent rings.
  • Ring D represents a nitrogen-containing five-membered ring represented by the formula (D3) that is fused at any position of two adjacent rings.
  • L is in agreement with the general formula (2), and Ar 2 in any one L represents an i + 1 monovalent substituted or unsubstituted aromatic heterocyclic group having 3 to 9 carbon atoms.
  • any one L in the general formula (3) is represented by the above formula (c5).
  • each X independently represents CH, C- or nitrogen, and at least one of X represents nitrogen.
  • Symbols common to the general formula (2) such as Ar 1 , Ar 3 to Ar 7 , d to i, and the like are the same.
  • L in the general formula (2) or the general formula (3) has at least one partial structure represented by the above formula (4).
  • the conformation number becomes a more preferable value.
  • the number of substitutions i in the formula (c5) is 2 to 4, and the 2 to 4 substituents are preferably different. Different substituents result in a loss of symmetry and more conformations.
  • L in the general formula (2) or the general formula (3) has at least two partial structures represented by the above formula (4). It is more preferable to have at least one partial structure represented by the above formula (5), and to have at least one partial structure represented by the above formula (5) on the nitrogen-containing six-membered ring in the formula (c5). Further preferred.
  • Ar 1 and Ar 3 to Ar 7 in formula (2) or formula (3) are preferably aromatic hydrocarbon groups having 6 carbon atoms, and the total number of Ar 1 to Ar 7 is 6 or more and 10 or less. It is preferable that
  • any one of Ar 3 to Ar 7 constituting L in the general formula (2) or the general formula (3) has at least one partial structure represented by the above formula (4) or the formula (5). desirable.
  • the compound for organic electroluminescence device of the present invention can be used alone as a material for organic electroluminescence device, but it can be used by using a plurality of compounds for organic electroluminescence device of the present invention or mixed with other compounds. By using it as a material for an electroluminescence device, the function can be further improved or the insufficient characteristics can be compensated.
  • a preferable compound that can be used by mixing with the compound for organic electroluminescence device of the present invention is not particularly limited as long as it is a known compound.
  • the organic electroluminescent device compound or material of the present invention is an organic layer such as a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, a hole blocking layer, or an electron blocking layer constituting the organic electroluminescent device. It can be used as a material, but among them, it is preferable to use as a hole transport layer, electron blocking layer, light emitting layer, electron transport layer, hole blocking layer material, and further, electron blocking layer, light emitting layer, hole blocking More preferably, it is used as a layer material.
  • one or more compounds of the present invention may be vapor-deposited from a vapor deposition source to form an organic layer.
  • the organic layer can also be formed by vapor deposition from different vapor deposition sources simultaneously with other compounds such as the material and phosphorescent material such as phosphorescence, fluorescence, and delayed fluorescence.
  • two or more kinds of the compounds of the present invention can be premixed to form a premix before vapor deposition, and the premix can be simultaneously vapor deposited from one vapor deposition source to form an organic layer.
  • one or more compounds of the present invention are premixed with a known host material or a luminescent dopant material such as phosphorescence, fluorescence, and delayed fluorescence to form a premix, and the premix is obtained from one deposition source.
  • the organic layer can also be formed by vapor deposition at the same time.
  • the compound used for premixing and the compound for organic electroluminescent elements of the present invention have a temperature difference of 30 ° C. or less at a desired vapor pressure.
  • the organic electroluminescent material can also be applied to various coating processes such as spin coating, bar coating, spraying, ink jet, and printing.
  • a solution also referred to as a composition for an organic electroluminescence device
  • the solvent is volatilized by heating and drying.
  • An organic layer can be formed.
  • the solvent used may be one kind or a mixture of two or more kinds.
  • the solution may contain a known host material or a luminescent dopant material such as phosphorescence, fluorescence, delayed fluorescence, etc. as a compound other than the present invention.
  • An additive or the like may be included.
  • FIG. 1 is a cross-sectional view showing an example of the structure of a general organic electroluminescence device used in the present invention.
  • 1 is a substrate
  • 2 is an anode
  • 3 is a hole injection layer
  • 4 is a hole transport layer
  • 5 is light emission.
  • Layer, 6 represents an electron transport layer
  • 7 represents a cathode.
  • the organic EL device of the present invention may have an exciton blocking layer adjacent to the light emitting layer, or may have an electron blocking layer between the light emitting layer and the hole injection layer.
  • the exciton blocking layer can be inserted on either the anode side or the cathode side of the light emitting layer, or both can be inserted simultaneously.
  • the organic electroluminescent device of the present invention has an anode, a light emitting layer, and a cathode as essential layers, but it is preferable to have a hole injecting and transporting layer and an electron injecting and transporting layer in addition to the essential layers. It is preferable to have a hole blocking layer between the injection transport layers.
  • the hole injection / transport layer means either or both of a hole injection layer and a hole transport layer
  • the electron injection / transport layer means either or both of an electron injection layer and an electron transport layer.
  • the structure opposite to that shown in FIG. 1, that is, the cathode 7, the electron transport layer 6, the light emitting layer 5, the hole transport layer 4 and the anode 2 can be laminated in this order on the substrate 1. Addition and omission are possible.
  • the organic electroluminescent device of the present invention is preferably supported on a substrate.
  • the substrate is not particularly limited, and any substrate that has been conventionally used for an organic electroluminescence device can be used.
  • a substrate made of glass, transparent plastic, quartz, or the like can be used.
  • anode material in the organic electroluminescence device a 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.
  • these electrode materials may be formed into a thin film by a method such as vapor deposition or sputtering, and a pattern having a desired shape may be formed by a photolithography method, or the pattern accuracy is not required (about 100 ⁇ m or more). May form a pattern through a mask having a desired shape at the time of vapor deposition or sputtering of the electrode material. Or when using the substance which can be apply
  • the transmittance be greater than 10%
  • 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.
  • the cathode material a material made of a metal having a small work function (4 eV or less) (referred to as an electron injecting metal), an alloy, an electrically conductive compound or a mixture thereof is used.
  • an electron injecting metal a material made of a metal having a small work function (4 eV or less) (referred to as an electron injecting metal), an alloy, an electrically conductive compound or a mixture thereof.
  • 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 such as a magnesium / silver mixture, magnesium, from the viewpoint of electron injectability and durability against oxidation, etc.
  • a magnesium / silver mixture, magnesium from the viewpoint of electron injectability and durability against oxidation, etc.
  • Aluminum mixtures, magnesium / indium mixtures, aluminum / aluminum oxide (Al 2 O 3 ) mixtures, lithium / aluminum mixtures, aluminum and the like are preferred.
  • the cathode can be produced by forming a thin film of these cathode materials by a method such as vapor deposition or sputtering.
  • the sheet resistance of 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 improved, which is convenient.
  • a transparent or translucent cathode can be produced by forming the conductive transparent material mentioned in the description of the anode on the cathode.
  • an element in which both the anode and the cathode are transmissive can be manufactured.
  • 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 layer includes a light emitting dopant material and a host material.
  • the organic electroluminescent element material of the present invention is suitably used as a host material in the light emitting layer.
  • one or a plurality of known host materials may be used in combination, but the amount used is 5 wt% or more and 95 wt% or less, preferably 20 wt% or more and 80 wt% or less with respect to the total of the host materials. Is good.
  • a known host material that can be used is preferably a compound that has a hole transporting ability and an electron transporting ability, prevents the emission of light from becoming longer, and has a high glass transition temperature.
  • Such other host materials are known from a large number of patent documents, and can be selected from them.
  • Specific examples of the host material are not particularly limited, but include indole derivatives, carbazole derivatives, indolocarbazole derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, Pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethylidene compounds, porphyrins Compounds, anthraquinodimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyran dioxide
  • Tetracarboxylic anhydride Tetracarboxylic anhydride, phthalocyanine derivatives, metal complexes of 8-quinolinol derivatives, metal phthalocyanines, various metal complexes represented by metal complexes of benzoxazole and benzothiazole derivatives, polysilane compounds, poly (N-vinylcarbazole) derivatives, Examples include aniline-based copolymers, thiophene oligomers, polythiophene derivatives, polyphenylene derivatives, polyphenylene vinylene derivatives, and polyfluorene derivatives.
  • the organic electroluminescent element material can be deposited from a vapor deposition source or dissolved in a solvent to form a solution, and then applied onto the hole injection transport layer and dried to form a light emitting layer.
  • organic electroluminescent element material When an organic electroluminescent element material is deposited to form an organic layer, other host materials and dopants may be deposited from different deposition sources together with the material of the present invention, or premixed before the deposition. By using a mixture, a plurality of host materials and dopants can be deposited simultaneously from one deposition source.
  • the material used for the hole injecting and transporting layer as the base has low solubility in the solvent used in the light emitting layer solution.
  • any of a fluorescent light-emitting dopant, a phosphorescent light-emitting dopant, and a delayed fluorescent light-emitting dopant may be used, but a phosphorescent light-emitting dopant and a delayed fluorescent light-emitting dopant are preferable in terms of light emission efficiency. Further, only one kind of these luminescent dopants may be contained, or two or more kinds of dopants may be contained.
  • the phosphorescent dopant preferably contains an organometallic complex containing at least one metal selected from ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum and gold.
  • organometallic complex containing at least one metal selected from ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum and gold.
  • iridium complexes described in J. Am. Chem. Soc. 2001, 123,4304 and JP-T-2013-53051 are preferably used, but are not limited thereto.
  • the content of the phosphorescent dopant material is preferably 0.1 to 30 wt%, more preferably 1 to 20 wt% with respect to the host material.
  • the phosphorescent dopant material is not particularly limited, and specific examples include the following.
  • the fluorescent dopant is not particularly limited.
  • benzoxazole derivatives benzothiazole derivatives, benzimidazole derivatives, styrylbenzene derivatives, polyphenyl derivatives, diphenylbutadiene derivatives, tetraphenylbutadiene derivatives, naphthalimide Derivatives, coumarin derivatives, condensed aromatic compounds, perinone derivatives, oxadiazole derivatives, oxazine derivatives, aldazine derivatives, pyralidine derivatives, cyclopentadiene derivatives, bisstyrylanthracene derivatives, quinacridone derivatives, pyrrolopyridine derivatives, thiadiazopyridine derivatives, styryl Amine derivatives, diketopyrrolopyrrole derivatives, aromatic dimethylidine compounds, metal complexes of 8-quinolinol derivatives and pyromethenes Conductor of metal
  • Preferred examples include condensed aromatic derivatives, styryl derivatives, diketopyrrolopyrrole derivatives, oxazine derivatives, pyromethene metal complexes, transition metal complexes, or lanthanoid complexes, more preferably naphthalene, pyrene, chrysene, triphenylene, benzo [c] phenanthrene.
  • the content of the fluorescent light-emitting dopant material is preferably 0.1 to 20%, more preferably 1 to 10% with respect to the host material.
  • the thermally activated delayed fluorescence emission dopant is not particularly limited, but a metal complex such as a tin complex or a copper complex, an indolocarbazole derivative described in WO2011 / 070963, Examples include cyanobenzene derivatives, carbazole derivatives described in Nature 2012, 492, 234, phenazine derivatives, oxadiazole derivatives, triazole derivatives, sulfone derivatives, phenoxazine derivatives, acridine derivatives, and the like described in Nature Photonics, 2014, 8, 326.
  • the content of the thermally activated delayed fluorescent light-emitting dopant material is preferably 0.1 to 90%, more preferably 1 to 50% with respect to the host material.
  • 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 hole blocking layer has a function of an electron transport layer in a broad sense, and is made of a hole blocking material that has a function of transporting electrons and has a remarkably small ability to transport holes. The probability of recombination of electrons and holes in the light emitting layer can be improved by preventing the above.
  • the hole blocking layer preferably contains the material of the present invention, but a known hole blocking layer material can also be used.
  • the electron blocking layer has the function of a hole transport layer in a broad sense. By blocking electrons while transporting holes, the probability of recombination of electrons and holes in the light emitting layer can be improved. .
  • the material for the electron blocking layer a known electron blocking layer material can be used, and the material for the hole transport layer described later can be used as necessary.
  • the thickness of the electron blocking layer is preferably 3 to 100 nm, more preferably 5 to 30 nm.
  • 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 between two adjacent light emitting layers in an element in which two or more light emitting layers are adjacent.
  • a known exciton blocking layer material can be used as the material for the exciton blocking layer.
  • Examples thereof include 1,3-dicarbazolylbenzene (mCP) and bis (2-methyl-8-quinolinolato) -4-phenylphenolatoaluminum (III) (BAlq).
  • 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 of hole injection or transport and electron barrier properties, and may be either organic or inorganic.
  • any known compound can be selected and used.
  • Examples of such hole transport materials include porphyrin derivatives, arylamine derivatives, triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives.
  • Porphyrin derivatives, arylamine derivatives, and styryl It is preferable to use an amine derivative, and it is more preferable to use an arylamine compound.
  • 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.
  • an electron transport material (which may also serve as a hole blocking material), it is sufficient if it has a function of transmitting electrons injected from the cathode to the light emitting layer.
  • any known compound can be selected and used.
  • polycyclic aromatic derivatives such as naphthalene, anthracene, phenanthroline, tris (8-quinolinolato) aluminum (III) Derivatives, phosphine oxide derivatives, nitro-substituted fluorene derivatives, diphenylquinone derivatives, thiopyrandioxide derivatives, carbodiimides, fluorenylidenemethane derivatives, anthraquinodimethane and anthrone derivatives, bipyridine derivatives, quinoline derivatives, oxadiazole derivatives, benzimidazoles Derivatives, benzothiazole derivatives, indolocarbazole derivatives and the like.
  • Conformational search calculation was performed for compounds 300, 122, 337, 338, 335, 339, 019, 600, 161, 181, 160, and compounds 1 to 10 for comparison, which were exemplified as the compounds for organic electroluminescence devices. .
  • Conformational search calculation is performed by inputting the atomic coordinates and bonding mode of the structure to be calculated into calculation software called CONFLEX (manufactured by CONFLEX), setting the conformational search range from the local stable structure to 20 kcal / mol, Calculation was performed by a dynamic method (force field: MMFF94s). Table 1 shows the calculation result of the conformation generated by the conformation search calculation. Note that any of the above compounds has a structure in which aromatic rings are linked and does not have a non-aromatic substituent, so that the compound itself has a skeleton structure that does not contain a substituent.
  • the compound numbers correspond to the numbers given to the above exemplified compounds and the numbers given to the following compounds for comparison.
  • Table 1 shows the results of a solubility test in toluene for the above compounds.
  • toluene was added so that each compound would be 1 wt%, and it was judged by the presence or absence of undissolved matter after ultrasonically stirring it in a water bath at a water temperature of 40 ° C. for 15 minutes.
  • A means no undissolved residue and B means undissolved residue.
  • Example 12 Each thin film was laminated at a vacuum degree of 4.0 ⁇ 10 ⁇ 5 Pa by a vacuum evaporation method on a glass substrate on which an anode made of ITO having a thickness of 110 nm was formed.
  • HAT-CN was formed as a hole injection layer with a thickness of 25 nm on ITO, and then NPD was formed as a hole transport layer with a thickness of 30 nm.
  • HT-1 was formed to a thickness of 10 nm as an electron blocking layer.
  • the compound 300 as a host and Ir (ppy) 3 as a light emitting dopant were co-deposited from different vapor deposition sources, and a light emitting layer was formed to a thickness of 40 nm.
  • the co-evaporation was performed under the deposition conditions in which the concentration of Ir (ppy) 3 was 10 wt%.
  • ET-1 was formed to a thickness of 20 nm as an electron transport layer.
  • lithium fluoride (LiF) was formed to a thickness of 1 nm as an electron injection layer on the electron transport layer.
  • aluminum (Al) was formed as a cathode to a thickness of 70 nm on the electron injection layer, and an organic EL device was produced.
  • Example 12 an organic EL device was produced in the same manner as in Example 12 except that any one of Compounds 122, 019, 600, 161, 181, and 160 was used as the host.
  • Example 12 an organic EL device was produced in the same manner as in Example 12 except that any one of Compounds 1, 2, or 3 was used as the host.
  • Table 2 shows the luminance, driving voltage, and luminance half-life of the produced organic EL device.
  • voltage, brightness, current efficiency, and power efficiency are values at a drive current of 20 mA / cm 2 , which are initial characteristics.
  • LT90 is the time required for the luminance to decay to 90% of the initial luminance at the initial luminance of 9000 cd / m 2 , and is a life characteristic. Note that all the characteristics (voltage, luminance, LT90) are expressed as relative values with the characteristics of the reference comparative example (comparative example 11 in Table 2) as 100%.
  • Example 19 Each thin film was laminated at a vacuum degree of 4.0 ⁇ 10 ⁇ 5 Pa by a vacuum evaporation method on a glass substrate on which an anode made of ITO having a thickness of 110 nm was formed.
  • HAT-CN was formed as a hole injection layer with a thickness of 25 nm on ITO, and then NPD was formed as a hole transport layer with a thickness of 30 nm.
  • HT-1 was formed to a thickness of 10 nm as an electron blocking layer.
  • compound 338 as a host and Ir (ppy) 3 as a light emitting dopant were co-deposited from different vapor deposition sources to form a light emitting layer with a thickness of 40 nm.
  • the co-evaporation was performed under the deposition conditions in which the concentration of Ir (ppy) 3 was 10 wt%.
  • ET-1 was formed to a thickness of 20 nm as an electron transport layer.
  • lithium fluoride (LiF) was formed to a thickness of 1 nm as an electron injection layer on the electron transport layer.
  • aluminum (Al) was formed as a cathode to a thickness of 70 nm on the electron injection layer, and an organic EL device was produced.
  • Example 20 and Comparative Examples 14 to 15 In Example 19, an organic EL device was produced in the same manner as in Example 19 except that any one of Compound 337, Compound 4, and Compound 5 was used as the host.
  • Table 3 shows the characteristics of the fabricated organic EL elements.
  • the reference comparative example is Comparative Example 14.
  • Example 21 Each thin film was laminated at a vacuum degree of 4.0 ⁇ 10 ⁇ 5 Pa by a vacuum evaporation method on a glass substrate on which an anode made of ITO having a thickness of 110 nm was formed.
  • HAT-CN was formed as a hole injection layer with a thickness of 25 nm on ITO, and then NPD was formed as a hole transport layer with a thickness of 30 nm.
  • HT-1 was formed to a thickness of 10 nm as an electron blocking layer.
  • compound 335 as a host and Ir (ppy) 3 as a light emitting dopant were co-deposited from different vapor deposition sources to form a light emitting layer with a thickness of 40 nm.
  • the co-evaporation was performed under the deposition conditions in which the concentration of Ir (ppy) 3 was 10 wt%.
  • ET-1 was formed to a thickness of 20 nm as an electron transport layer.
  • lithium fluoride (LiF) was formed to a thickness of 1 nm as an electron injection layer on the electron transport layer.
  • aluminum (Al) was formed as a cathode to a thickness of 70 nm on the electron injection layer, and an organic EL device was produced.
  • Example 21 an organic EL device was produced in the same manner as in Example 21 except that Compound 6 was used as the host.
  • Table 4 shows the characteristics of the fabricated organic EL elements.
  • the reference comparative example is Comparative Example 16.
  • Example 22 Each thin film was laminated at a vacuum degree of 4.0 ⁇ 10 ⁇ 5 Pa by a vacuum evaporation method on a glass substrate on which an anode made of ITO having a thickness of 110 nm was formed.
  • HAT-CN was formed as a hole injection layer with a thickness of 25 nm on ITO, and then NPD was formed as a hole transport layer with a thickness of 30 nm.
  • HT-1 was formed to a thickness of 10 nm as an electron blocking layer.
  • the compound 339 as a host and Ir (ppy) 3 as a light emitting dopant were co-deposited from different vapor deposition sources to form a light emitting layer with a thickness of 40 nm.
  • the co-evaporation was performed under the deposition conditions in which the concentration of Ir (ppy) 3 was 10 wt%.
  • ET-1 was formed to a thickness of 20 nm as an electron transport layer.
  • lithium fluoride (LiF) was formed to a thickness of 1 nm as an electron injection layer on the electron transport layer.
  • aluminum (Al) was formed as a cathode to a thickness of 70 nm on the electron injection layer, and an organic EL device was produced.
  • Comparative Example 17 An organic EL device was produced in the same manner as in Example 22 except that Compound 7 was used as the host in Example 22.
  • Table 5 shows the characteristics of the fabricated organic EL elements.
  • the reference comparative example is Comparative Example 17.
  • Example 27 Solvent-cleaned, UV ozone-treated glass substrate with ITO having a film thickness of 150 nm, poly (3,4-ethylenedioxythiophene) / polystyrene sulfonic acid (PEDOT / PSS) as a hole injection layer: (HCC Stark) Co., Ltd., trade name: Clevios PCH8000) was formed to a film thickness of 25 nm.
  • PEDOT / PSS polystyrene sulfonic acid
  • the solvent was removed with a hot plate at 150 ° C.
  • thermosetting film is a film having a crosslinked structure and is insoluble in a solvent.
  • This thermosetting film is a hole transport layer (HTL).
  • HTL hole transport layer
  • Alq 3 was formed to a thickness of 35 nm
  • LiF / Al was formed to a thickness of 170 nm as a cathode
  • this element was sealed in a glove box to produce an organic electroluminescent element.
  • Example 28 Comparative Example 20 In Example 27, an organic EL device was produced in the same manner as in Example 27 except that Compound 160, 122, or 1 was used as the host.
  • Table 6 shows the characteristics of the fabricated organic EL elements.
  • the reference comparative example is Comparative Example 20.
  • Examples 35 to 36, Comparative Examples 22 to 23 An organic thin film was formed by depositing any one of the compounds 300 and 122, which are the materials for an organic electroluminescent element of the present invention, and the comparative compounds 1 and 2 on a silicon substrate by a vacuum deposition method. The substrate on which this organic thin film was formed was heated at the glass transition temperature of the material for 24 hours under a nitrogen atmosphere, and then amorphous stability was determined by visual observation of the thin film and measurement of out-of-plane X-ray diffraction. Evaluated.
  • Table 7 shows the results of amorphous stability evaluated in Examples 35 to 36 and Comparative Examples 22 to 23.
  • C indicates crystallization and A indicates no crystallization.
  • XRD measurement result after the heating of Example 35 and Comparative Example 22 is shown in FIG.
  • Example 35 is indicated by a solid line
  • Comparative Example 22 is indicated by a dotted line.
  • the organic electroluminescence device using the compound for organic electroluminescence device of the present invention has excellent light emission characteristics and excellent life characteristics.
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KR20230099693A (ko) 2021-12-27 2023-07-04 가부시키가이샤 한도오따이 에네루기 켄큐쇼 유기 화합물, 발광 디바이스, 박막, 발광 장치, 전자 기기, 및 조명 장치

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