WO2021020285A1 - 環状アジン化合物、有機電界発光素子用材料、有機電界発光素子用電子輸送材料、および有機電界発光素子 - Google Patents
環状アジン化合物、有機電界発光素子用材料、有機電界発光素子用電子輸送材料、および有機電界発光素子 Download PDFInfo
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- WO2021020285A1 WO2021020285A1 PCT/JP2020/028488 JP2020028488W WO2021020285A1 WO 2021020285 A1 WO2021020285 A1 WO 2021020285A1 JP 2020028488 W JP2020028488 W JP 2020028488W WO 2021020285 A1 WO2021020285 A1 WO 2021020285A1
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- organic electroluminescent
- layer
- compound
- cyclic azine
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- -1 Cyclic azine compound Chemical class 0.000 title claims abstract description 157
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- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 150000008376 fluorenones Chemical class 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- WIAWDMBHXUZQGV-UHFFFAOYSA-N heptacyclo[13.10.1.12,6.011,26.017,25.018,23.010,27]heptacosa-1(25),2,4,6(27),7,9,11,13,15(26),17,19,21,23-tridecaene Chemical group C=12C3=CC=CC2=CC=CC=1C1=CC=CC2=C1C3=C1C=C3C=CC=CC3=C1C2 WIAWDMBHXUZQGV-UHFFFAOYSA-N 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 229910052976 metal sulfide Inorganic materials 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- BBDFECYVDQCSCN-UHFFFAOYSA-N n-(4-methoxyphenyl)-4-[4-(n-(4-methoxyphenyl)anilino)phenyl]-n-phenylaniline Chemical group C1=CC(OC)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC(OC)=CC=1)C1=CC=CC=C1 BBDFECYVDQCSCN-UHFFFAOYSA-N 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- USPVIMZDBBWXGM-UHFFFAOYSA-N nickel;oxotungsten Chemical compound [Ni].[W]=O USPVIMZDBBWXGM-UHFFFAOYSA-N 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 150000007978 oxazole derivatives Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- GPRIERYVMZVKTC-UHFFFAOYSA-N p-quaterphenyl Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)C=C1 GPRIERYVMZVKTC-UHFFFAOYSA-N 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 150000003219 pyrazolines Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- SBIBMFFZSBJNJF-UHFFFAOYSA-N selenium;zinc Chemical compound [Se]=[Zn] SBIBMFFZSBJNJF-UHFFFAOYSA-N 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N serine Chemical compound OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Images
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- 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
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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- C07D487/12—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 three hetero rings
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
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Definitions
- the present disclosure relates to cyclic azine compounds, materials for organic electroluminescent devices, electron transport materials for organic electroluminescent devices, and organic electroluminescent devices.
- Patent Document 1 discloses a cyclic azine compound having a specific substituent, which is excellent in heat resistance, has a low driving voltage, and contributes to the provision of a long-life organic electroluminescent device as a material for an organic electroluminescent device. ..
- the market demand for organic electroluminescent devices in recent years has become higher and higher, and the development of materials that have both excellent drive voltage characteristics and current efficiency characteristics is required.
- the organic electroluminescent device using the cyclic azine compound disclosed in Patent Document 1 exhibits excellent long-life characteristics and current efficiency characteristics, but further improvement in drive voltage characteristics is required.
- One aspect of the present disclosure is directed to providing a cyclic azine compound, a material for an organic electroluminescent device, and an electron transporting material for an organic electroluminescent device that have both excellent drive voltage characteristics and current efficiency characteristics. Furthermore, another aspect of the present disclosure is directed to providing an organic electroluminescent device that has both excellent drive voltage characteristics and current efficiency characteristics.
- the cyclic azine compound represented by the formula (1) is provided:
- Ar 1 is a phenyl group, or a 4-biphenylyl group
- Ar 2 is any one of the groups represented by the formulas (2-1) to (2-3);
- Ar 3 is a group represented by the formula (3)
- Ar 31 is Hydrogen atom or It is any one of the groups represented by the formulas (2-1) to (2-3).
- a material for an organic electroluminescent device containing the cyclic azine compound is provided.
- an electron transport material for an organic electroluminescent device containing the cyclic azine compound is provided.
- an organic electroluminescent device containing the cyclic azine compound is provided.
- a cyclic azine compound having both excellent drive voltage characteristics and current efficiency characteristics, a material for an organic electroluminescent device, and an electron transport material for an organic electroluminescent device can be obtained.
- an organic electroluminescent device having both excellent drive voltage characteristics and current efficiency characteristics can be obtained.
- Ar 1 is a phenyl group, or a 4-biphenylyl group
- Ar 2 is a group represented by any one of the formulas (2-1) to (2-3);
- Ar 3 is a group represented by the formula (3)
- Ar 31 is Hydrogen atom or It is a group represented by any one of the formulas (2-1) to (2-3).
- the cyclic azine compound represented by the formula (1) may be referred to as the cyclic azine compound (1).
- substituents in the cyclic azine compound (1) and preferred specific examples thereof are as follows.
- Ar 2 is a group represented by any one of the formulas (2-1) to (2-3).
- Ar 2 has both excellent drive voltage characteristics and current efficiency characteristics, and is described in the formulas (2-1), (2-2a), (2-2b), (2-3a), or (2-3b). It is more preferable that the group is represented by.
- Ar 3 is a group represented by the formula (3);
- Ar 31 is Hydrogen atom or It is a group represented by any one of the formulas (2-1) to (2-3).
- Ar 3 is preferably a group represented by any one of the formulas (3-1) to (3-9) in that it has both excellent drive voltage characteristics and current efficiency characteristics.
- the cyclic azine compound (1) When the cyclic azine compound (1) is used as a part of a component of an organic electroluminescent element (OLED; Organic Light Emitting Diode), effects such as high current efficiency and low drive voltage can be obtained. In particular, when the cyclic azine compound (1) is used as an electron transport layer, these effects are further exhibited.
- OLED Organic Light Emitting Diode
- cyclic azine compound (1) The cyclic azine compound represented by any one of the compounds (1-1) to (1-90) shown in Tables 1 to 3 is more suitable in terms of achieving both excellent drive voltage characteristics and current efficiency characteristics. preferable.
- cyclic azine compounds shown in Tables 1 to 3 the formulas (1-6), (1-15), (1-48), (1-49), (1-51), (1-52) , (1-54), (1-64), (1-65), (1-66), (1-67), (1-71), (1-73) or (1-82).
- the cyclic azine compound is particularly preferable in that it has both excellent drive voltage characteristics and current efficiency characteristics of the device.
- the cyclic azine compound (1) is not particularly limited, but can be used, for example, as a material for an organic electroluminescent device. Further, the cyclic azine compound (1) can be used, for example, as an electron transport material for an organic electroluminescent device.
- the material for an organic electroluminescent device according to one aspect of the present disclosure contains a cyclic azine compound (1).
- the electron transport material for an organic electroluminescent device according to one aspect of the present disclosure includes a cyclic azine compound (1).
- the material for an organic electroluminescent device and the electron transporting material for an organic electroluminescent device containing the cyclic azine compound (1) contribute to the production of an organic electroluminescent device having both excellent drive voltage characteristics and current efficiency characteristics.
- the organic electroluminescent device includes a cyclic azine compound (1).
- the configuration of the organic electroluminescent device is not particularly limited, and examples thereof include the configurations (i) to (vii) shown below.
- FIG. 1 is a schematic cross-sectional view showing an example of a laminated structure of an organic electroluminescent device containing a cyclic azine compound according to one aspect of the present disclosure.
- the organic electroluminescence device shown in FIG. 1 has a so-called bottom emission type element configuration, but the organic electroluminescence device according to one aspect of the present disclosure is limited to the bottom emission type element configuration. is not it. That is, the organic electroluminescence device according to one aspect of the present disclosure may have a top emission type device configuration or another known device configuration.
- the organic electroluminescent device 100 includes a substrate 1, an anode 2, a hole injection layer 3, a charge generation layer 4, a hole transport layer 5, a light emitting layer 6, an electron transport layer 7, and a cathode 8 in this order.
- some of these layers may be omitted, and conversely, other layers may be added.
- an electron injection layer may be provided between the electron transport layer 7 and the cathode 8, the charge generation layer 4 is omitted, and the hole transport layer 5 is directly provided on the hole injection layer 3. May be good.
- a single layer having a function of a plurality of layers such as an electron injection / transport layer having a function of an electron injection layer and a function of an electron transport layer in a single layer, is provided as a plurality of layers. It may be a configuration provided instead of. Further, for example, the single-layer hole transport layer 5 and the single-layer electron transport layer 7 may each be composed of a plurality of layers.
- the organic electroluminescent device contains a cyclic azine compound represented by the above formula (1) in one or more layers selected from the group consisting of a light emitting layer and a layer between the light emitting layer and the cathode. Therefore, in the configuration example shown in FIG. 1, the organic electroluminescent device 100 contains the cyclic azine compound (1) in at least one layer selected from the group consisting of the light emitting layer 6 and the electron transport layer 7. In particular, it is preferable that the electron transport layer 7 contains the cyclic azine compound (1).
- the cyclic azine compound (1) may be contained in a plurality of layers included in the organic electroluminescent device, and when an electron injection layer is provided between the electron transport layer and the cathode, the electron injection layer is provided.
- the cyclic azine compound (1) may be contained.
- the organic electroluminescent device 100 in which the electron transport layer 7 contains the cyclic azine compound (1) will be described.
- the substrate is not particularly limited, and examples thereof include a glass plate, a quartz plate, and a plastic plate. Further, in the case of a configuration in which light emission is taken out from the substrate 1 side, the substrate 1 is transparent with respect to the wavelength of light.
- the light-transmitting plastic film examples include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyetheretherketone, polyphenylene sulfide, polyarylate, polyimide, and polycarbonate (Plastic film).
- PET polyethylene terephthalate
- PEN polyethylene naphthalate
- PES polyethersulfone
- polyetherimide polyetheretherketone
- polyphenylene sulfide polyarylate
- polyimide polycarbonate
- PC cellulose triacetate
- CAP cellulose acetate propionate
- An anode 2 is provided on the substrate 1 (on the hole injection layer 3 side).
- the anode is formed of a material that allows or substantially passes the light emission.
- the transparent material used for the anode is not particularly limited, but for example, indium-tin oxide (ITO; Indium Tin Oxide), indium-zinc oxide (IZO; Indium Zinc Oxide), tin oxide, aluminum.
- ITO Indium-tin oxide
- IZO Indium Zinc Oxide
- tin oxide aluminum.
- anode In the case of an organic electroluminescent device having a configuration in which light is extracted only from the cathode side, the transmission characteristics of the anode are not important. Therefore, examples of the material used for the anode in this case include gold, iridium, molybdenum, palladium, platinum and the like.
- a buffer layer electrode interface layer may be provided on the anode.
- a hole injection layer 3, a charge generating layer 4 described later, and a hole transport layer 5 are provided in this order from the anode 2 side.
- the hole injection layer and the hole transport layer have a function of transmitting holes injected from the anode to the light emitting layer, and the hole injection layer and the hole transport layer are interposed between the anode and the light emitting layer. As a result, more holes are injected into the light emitting layer at a lower electric field.
- the hole injection layer and hole transport layer also function as electron barrier layers. That is, the electrons injected from the cathode and transported from the electron injection layer and / or the electron transport layer to the light emitting layer are generated by the electron barrier existing at the interface between the light emitting layer and the hole injection layer and / or the hole transport layer. , Leakage into the hole injection layer and / or the hole transport layer is suppressed. As a result, the electrons are accumulated at the interface in the light emitting layer to bring about effects such as improvement of current efficiency, and an organic electroluminescent device having excellent light emitting performance can be obtained.
- the material of the hole injection layer and the hole transport layer has at least one of hole injection property, hole transport property, and electron barrier property.
- the material of the hole injection layer and the hole transport layer may be either an organic substance or an inorganic substance.
- the materials for the hole injection layer and the hole transport layer include triazole derivative, oxadiazole derivative, imidazole derivative, polyarylalkane derivative, pyrazoline derivative, pyrazolone derivative, phenylenediamine derivative, arylamine derivative, and amino-substituted chalcone.
- aromatic tertiary amine compound and the styrylamine compound include N, N, N', N'-tetraphenyl-4,4'-diaminophenyl, N, N'-diphenyl-N, N'-.
- the hole injection layer and the hole transport layer may have a single-layer structure made of one or more kinds of materials, or may have a laminated structure made of a plurality of layers having the same composition or different compositions.
- a charge generation layer 4 may be provided between the hole injection layer 3 and the hole transport layer 5.
- the material of the charge generation layer is not particularly limited, but for example, dipyrazino [2,3-f: 2', 3'-h] quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT). -CN).
- the charge generation layer may have a single-layer structure composed of one or more kinds of materials, or may have a laminated structure composed of a plurality of layers having the same composition or different compositions.
- a light emitting layer 6 is provided between the hole transport layer 5 and the electron transport layer 7, which will be described later.
- Examples of the material of the light emitting layer include a phosphorescent material, a fluorescent material, and a thermally activated delayed fluorescent material. In the light emitting layer, electron-hole pairs are recombined, resulting in light emission.
- the light emitting layer may consist of a single low molecular weight material or a single polymer material, but more generally it consists of a host material doped with a guest compound. The luminescence comes primarily from the dopant and can have any color.
- Examples of the host material include compounds having a biphenyl group, a fluorenyl group, a triphenylsilyl group, a carbazole group, a pyrenyl group, and an anthryl group. More specifically, DPVBi (4,4'-bis (2,2-diphenylvinyl) -1,1'-biphenyl), BCzVBi (4,4'-bis (9-ethyl-3-carbazobinylene) 1, 1'-biphenyl), TBADN (2-talmostutyl-9,10-di (2-naphthyl) anthracene), ADN (9,10-di (2-naphthyl) anthracene), CBP (4,4'-bis) (Carbazole-9-yl) biphenyl), CDBP (4,4'-bis (carbazole-9-yl) -2,2'-dimethylbiphenyl), 2- (9-phenylcarbazole
- Examples of the fluorescent dopant include anthracene, pyrene, tetracene, xanthene, perylene, lubrene, coumarin, rhodamine, quinacridone, dicyanomethylenepyrane compound, thiopyran compound, polymethine compound, pyrylium, thiapyrylium compound, fluorene derivative, periversene derivative and indenoperylene. Derivatives, bis (azinyl) amine boron compounds, bis (azinyl) methane compounds, carbostyryl compounds, and the like can be mentioned.
- the fluorescent dopant may be a combination of two or more selected from these.
- Examples of the phosphorescent dopant include metal complexes such as iridium complex, platinum complex, palladium complex, and osmium complex.
- the fluorescent dopant and the phosphorescent dopant include Alq3 (tris (8-hydroxyquinolinolato) aluminum), DPAVBi (4,4'-bis [4- (di-p-tolylamino) styryl] biphenyl), perylene, Bis [2- (4-n-hexylphenyl) quinoline] (acetylacetonate) iridium (III), Ir (PPy) 3 (tris (2-phenylpyridine) iridium (III)), and FIrPic (bis (3,3) 5-difluoro-2- (2-pyridyl) phenyl- (2-carboxypyridyl) iridium (III))) and the like can be mentioned.
- the thermal activated delayed fluorescence material can be used as either the host material or the guest material described above.
- the thermally activated delayed fluorescence light emitting material itself does not emit light, and can also play a role of efficiently transferring excitation energy to the fluorescent dopant forming the light emitting layer at the same time as the thermally activated delayed fluorescence emitting material.
- thermally activated delayed fluorescence examples include 4Cz-IPN (2,4,5,6-tetra (9-carbazolyl) -isophthalonitrile), 5Cz-BN (2,3,4,5,6- Penta (9-carbazolyl) -benzonitrile), DACTII (2- [3,6-bis (diphenylamino) carbazole-9-ylphenyl] -4,6-diphenyl-1,3,5-triazine) and the like. Be done.
- the light emitting material is not limited to being contained only in the light emitting layer.
- the light emitting material may contain a layer (hole transport layer 5 or electron transport layer 7) adjacent to the light emitting layer. This makes it possible to further increase the current efficiency of the organic electroluminescent device.
- the light emitting layer may have a single layer structure made of one or more kinds of materials, or may have a laminated structure made of a plurality of layers having the same composition or different compositions.
- An electron transport layer 7 is provided between the light emitting layer 6 and the cathode 8 described later.
- the electron transport layer has a function of transferring electrons injected from the cathode to the light emitting layer. By interposing the electron transport layer between the cathode and the light emitting layer, electrons are injected into the light emitting layer with a lower electric field.
- the electron transport layer preferably contains the cyclic azine compound represented by the above formula (1).
- the electron transport layer may further contain a conventionally known electron transport material in addition to the cyclic azine compound (1).
- Conventionally known electron transport materials include, for example, 8-hydroxyquinolinolatrithium (Liq), bis (8-hydroxyquinolinolato) zinc, bis (8-hydroxyquinolinolato) copper, and bis (8-hydroxyquino).
- Linolato) manganese tris (8-hydroxyquinolinolato) aluminum, tris (2-methyl-8-hydroxyquinolinolato) aluminum, tris (8-hydroxyquinolinolato) gallium, bis (10-hydroxybenzo [h] ] Kinolinolato) berylium, bis (10-hydroxybenzo [h] quinolinolato) zinc, bis (2-methyl-8-quinolinolato) chlorogallium, bis (2-methyl-8-quinolinolato) (o-cresolate) gallium, bis ( 2-Methyl-8-quinolinolato) -1-naphtholate aluminum, or bis (2-methyl-8-quinolinolato) -2-naphtholate gallium, 2- [3- (9-phenanthrenyl) -5- (3-pyridinyl) ) Phenyl] -4,6-diphenyl-1,3,5-triazine, and 2- (4,''-di-2-pyridinyl
- the electron transport layer may have a single-layer structure composed of one or more kinds of materials, or may have a laminated structure composed of a plurality of layers having the same composition or a different composition.
- the electron transport layer has a two-layer structure in which the light emitting layer side is the first electron transport layer and the cathode side is the second electron transport layer, it is preferable that the second electron transport layer contains the cyclic azine compound (1).
- a cathode 8 is provided on the electron transport layer 7.
- the cathode can be formed from any conductive material.
- Materials for the cathode 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 ) mixture, indium. , Lithium / aluminum mixture, rare earth metals and the like.
- a buffer layer may be provided on the cathode (electron transport layer side).
- the material of each layer (with a material such as a binder resin and a solvent if necessary) can be used, for example, by vacuum deposition method, spin coating method, casting method, LB ( It can be formed by thinning by a known method such as the Langmuir-Blodgett method) method.
- the film thickness of each layer formed in this manner is not particularly limited and may be appropriately selected depending on the situation, but is usually in the range of 5 nm to 5 ⁇ m.
- the anode and cathode can be formed by thinning the electrode material by a method such as vapor deposition or sputtering.
- a pattern may be formed through a mask having a desired shape during vapor deposition or sputtering, or a thin film may be formed by vapor deposition or sputtering, and then a pattern having a desired shape may be formed by photolithography.
- the film thickness of the anode and the cathode is preferably 1 ⁇ m or less, and more preferably 10 nm or more and 200 nm or less.
- the organic electroluminescent element according to one aspect of the present disclosure may be used as a kind of lamp such as an illumination or an exposure light source, a projection device of a type that projects an image, or a still image or a moving image that is directly visually recognized. It may be used as a display device (display) of the type to be used.
- the drive method may be either a simple matrix (passive matrix) method or an active matrix method.
- a full-color display device can be manufactured by using two or more kinds of organic electroluminescent devices of the present embodiment having different emission colors.
- the cyclic azine compound (1) according to one aspect of the present disclosure can be synthesized by appropriately combining known reactions (for example, Suzuki-Miyaura cross-coupling reaction).
- the cyclic azine compound (1) according to one aspect of the present disclosure can be synthesized according to the production method represented by any one of the reaction formulas (a) to (f) shown below. It is not to be interpreted in a limited way.
- Ar 1 , Ar 2 , and Ar 3 have the same definition as the formula (1).
- X 2 and X 3 each independently represent a leaving group.
- the leaving group is not particularly limited, and examples thereof include a chlorine atom, a bromine atom, an iodine atom, and a trifluoromethanesulfonyloxy group.
- a bromine atom or a chlorine atom is preferable in terms of good reaction yield.
- Y 2 and Y 3 independently represent the metal-containing groups ZnR 1 , MgR 2 , or Sn (R 3 ) 3 ; or the boron-containing group B (OR 4 ) 2 ;.
- R 1 and R 2 independently represent a chlorine atom, a bromine atom or an iodine atom
- R 3 represents an alkyl group or a phenyl group having 1 to 4 carbon atoms
- R 4 represents a hydrogen atom and a carbon number of carbon atoms. 1 from an alkyl group or a phenyl group 4
- B (oR 4) 2 two R 4 2 may be the same or different. Further, two R 4 may form a ring containing an oxygen atom and a boron atom together.
- ZnR 1 and MgR 2 examples include ZnCl, ZnBr, ZnI, MgCl, MgBr, MgI and the like.
- Sn (R 3 ) 3 examples include Sn (Me) 3 , Sn (Bu) 3, and the like.
- B (OR 4 ) 2 in the case where the two R 4s are integrated to form a ring containing an oxygen atom and a boron atom is not particularly limited, but the following (I)
- the group represented by (VI) can be exemplified, and the group represented by (II) is desirable in terms of good yield.
- reaction formulas (a) to (d) The production methods represented by the reaction formulas (a) to (d) will be described in more detail by taking the production method represented by the reaction formula (a) as an example.
- Process represented by the reaction formula (a) is the presence of a palladium catalyst, indicating that the obtained cyclic azine compound (1) by using the sequential reaction Y 2 -Ar 2, and Y 3 -Ar 3.
- Y 2- Ar 2 and Y 3- Ar 3 used in the reaction can be used at the same time to react, and the intermediate product obtained by reacting with Y 2- Ar 2 is once isolated.
- the presence of a palladium catalyst, Y 3 -Ar 3 can also be obtained cyclic azine compound (1) by reacting with a.
- the cyclic azine compound (1) can also be obtained by using Y 3- Ar 3 in the reaction first.
- reaction formulas (e) and (f) The production methods represented by the reaction formulas (e) and (f) will be described by taking the production method represented by the reaction formula (e) as an example.
- Process represented by the reaction formula (e) is the presence of a palladium catalyst, indicating that the obtained cyclic azine compound (1) by using the X 3 -Ar 3 to the reaction.
- the cyclic azine compound as a raw material used in the production methods represented by the reaction formulas (e) and (f) can be produced according to, for example, International Publication No. 2017/025164. Moreover, you may use a commercially available product.
- the production method represented by the reaction formula (e) or (f) is preferable in that the obtained cyclic azine compound (1) has a high purity.
- the production method according to one aspect of the present disclosure is a method for producing a cyclic azine compound represented by the formula (1). Including reacting the compound represented by the formula (4) with the compound represented by the formula (5):
- Ar 1 is a phenyl group, or a 4-biphenylyl group
- Ar 2 is a group represented by any one of the formulas (2-1) to (2-3);
- Ar 3 is a group represented by the formula (3)
- Ar 31 is Hydrogen atom or It is a group represented by any one of the formulas (2-1) to (2-3); X 4 is a leaving group; Y 4 is a halogen atom, a metal-containing group or a boron-containing group.
- the definition of the leaving group in the formula (4) is the same as the definition of the leaving group in the reaction formulas (a) to (f) described above.
- the definition of the metal-containing group or the boron-containing group in the formula (5) is the same as the definition of the leaving group in the reaction formulas (a) to (f) described above.
- the pyridine compound according to one aspect of the present disclosure is a pyridine compound represented by the formula (5):
- Ar 2 is a group represented by any one of the formulas (2-1) to (2-3);
- Ar 3 is a group represented by the formula (3)
- Ar 31 is Hydrogen atom or It is a group represented by any one of the formulas (2-1) to (2-3); Y 4 is a halogen atom, a metal-containing group or a boron-containing group.
- the definition of the metal-containing group or the boron-containing group in the formula (5) is the same as the definition of the leaving group in the reaction formulas (a) to (f) described above.
- the pyridine compound represented by the formula (5) is preferably a pyridine compound represented by the formula (5-1), (5-2) or (5-3):
- the measurement of the 1 H-NMR spectrum was performed using Gemini 200 (manufactured by Varian) or Bruker ASCEND 400 (400 MHz; manufactured by BRUKER).
- the light emitting characteristics of the organic electroluminescent device were evaluated by applying a direct current to the manufactured device at room temperature and using a luminance meter (product name: BM-9, manufactured by Topcon Techno House).
- Device Example-1 (see FIG. 2) (Preparation of substrate 101 and anode 102)
- a glass substrate with an ITO transparent electrode in which a 2 mm wide indium tin oxide (ITO) film (thickness 110 nm) was patterned in a stripe shape was prepared. Then, after cleaning this substrate with isopropyl alcohol, surface treatment was performed by ozone ultraviolet cleaning.
- ITO indium tin oxide
- each layer was vacuum-deposited by a vacuum-film deposition method on the surface-treated substrate after cleaning, and each layer was laminated and formed.
- the glass substrate was introduced into a vacuum vapor deposition tank, and the pressure was reduced to 1.0 ⁇ 10 -4 Pa. Then, each layer was produced in the following order according to the film forming conditions of each layer.
- the sublimated and purified HTL was formed into a film at a rate of 0.15 nm / sec at 85 nm to prepare a first hole transport layer 1051.
- the sublimated and purified EBL-3 was formed into a 5 nm film at a rate of 0.15 nm / sec to prepare a second hole transport layer 1052.
- the sublimated and purified HBL-1 was formed into a 6 nm film at a rate of 0.05 nm / sec to prepare a first electron transport layer 1071.
- cathode 108 a metal mask was arranged so as to be orthogonal to the ITO stripe on the substrate, and a cathode 108 was formed.
- silver / magnesium mass ratio 1/10
- silver were formed in this order at 80 nm and 20 nm, respectively, to form a two-layer structure.
- the film formation rate of silver / magnesium was 0.5 nm / sec, and the film formation rate of silver was 0.2 nm / sec.
- the 2 organic electroluminescent device 100 having a light emitting area of 4 mm as shown in FIG. 2 was manufactured.
- Each film thickness was measured with a stylus type film thickness measuring meter (DEKTAK, manufactured by Bruker).
- this device was sealed in a nitrogen atmosphere glove box having an oxygen and water concentration of 1 ppm or less.
- the sealing was performed by using a glass sealing cap and a film-forming substrate (element) with a bisphenol F type epoxy resin (manufactured by Nagase ChemteX Corporation).
- Element comparison example-1 An organic electroluminescent device was produced and evaluated in the same manner as in Device Example-1 except that ETL-1 was used instead of Compound 1-48 in Device Example-1. The obtained measurement results are shown in Table 4.
- Element reference example-1 An organic electroluminescent device was produced and evaluated in the same manner as in Device Example-1 except that ETL-2 described in Patent Document 1 was used instead of Compound 1-48 in Device Example-1. .. The obtained measurement results are shown in Table 4.
- Element reference example-2 An organic electroluminescent device was produced and evaluated in the same manner as in Device Example-1 except that ETL-3 described in Patent Document 1 was used instead of Compound 1-48 in Device Example-1. .. The obtained measurement results are shown in Table 4.
- Element reference example-3 An organic electroluminescent device was produced in the same manner as in Device Example-1 except that ETL-4 described in JP-A-2017-105717 was used instead of Compound 1-48 in Device Example-1. And evaluated. The obtained measurement results are shown in Table 4.
- Element Example-2 (see FIG. 3) (Preparation of substrate 101 and anode 102)
- a substrate having an anode on its surface a glass substrate with an ITO transparent electrode in which a 2 mm wide indium tin oxide (ITO) film (thickness 110 nm) was patterned in a stripe shape was prepared. Then, after cleaning this substrate with isopropyl alcohol, surface treatment was performed by ozone ultraviolet cleaning.
- ITO indium tin oxide
- each layer was vacuum-deposited by a vacuum-film deposition method on the surface-treated substrate after cleaning, and each layer was laminated and formed.
- the glass substrate was introduced into a vacuum vapor deposition tank, and the pressure was reduced to 1.0 ⁇ 10 -4 Pa. Then, each layer was produced in the following order according to the film forming conditions of each layer.
- the sublimated and purified HTL was formed into a 10 nm film at a rate of 0.15 nm / sec to prepare a first hole transport layer 1051.
- the sublimated and purified EBL-2 was formed into a 5 nm film at a rate of 0.15 nm / sec to prepare a second hole transport layer 1052.
- the sublimated and purified HBL-2 was formed into a 5 nm film at a rate of 0.05 nm / sec to prepare a first electron transport layer 1071.
- cathode 108 a metal mask was arranged so as to be orthogonal to the ITO stripe on the substrate, and a cathode 108 was formed.
- silver / magnesium mass ratio 1/10
- silver were formed in this order at 80 nm and 20 nm, respectively, to form a two-layer structure.
- the film formation rate of silver / magnesium was 0.5 nm / sec, and the film formation rate of silver was 0.2 nm / sec.
- the 2 organic electroluminescent device 100 having a light emitting area of 4 mm as shown in FIG. 3 was manufactured.
- Each film thickness was measured with a stylus type film thickness measuring meter (DEKTAK, manufactured by Bruker).
- this device was sealed in a nitrogen atmosphere glove box having an oxygen and water concentration of 1 ppm or less.
- the sealing was performed by using a glass sealing cap and a film-forming substrate (element) with a bisphenol F type epoxy resin (manufactured by Nagase ChemteX Corporation).
- a direct current was applied to the organic electroluminescent device produced as described above, and the light emission characteristics were evaluated using a luminance meter (product name: BM-9, manufactured by Topcon Technohouse Co., Ltd.).
- a luminance meter product name: BM-9, manufactured by Topcon Technohouse Co., Ltd.
- the drive voltage is a relative value using the result in the element reference example 2 described later as a reference value (100). The obtained measurement results are shown in Table 5.
- Element Example-3 An organic electroluminescent device was produced and evaluated in the same manner as in Device Example-2, except that Compound 1-49 was used instead of Compound 1-48 in Device Example-2. The obtained measurement results are shown in Table 5.
- Element Example-4 An organic electroluminescent device was produced in the same manner as in Device Example-2, except that Compound 1-50 synthesized in Synthesis Example-5 was used instead of Compound 1-48 in Device Example-2. evaluated. The obtained measurement results are shown in Table 5.
- Element Example-5 An organic electroluminescent device was produced in the same manner as in Device Example-2, except that Compound 1-51 synthesized in Synthesis Example-6 was used instead of Compound 1-48 in Device Example-2. evaluated. The obtained measurement results are shown in Table 5.
- Element Example-6 An organic electroluminescent device was produced and evaluated in the same manner as in Device Example-2, except that compound 1-52 was used instead of compound 1-48 in device example-2. The obtained measurement results are shown in Table 5.
- Element Example-7 An organic electroluminescent device was produced and evaluated in the same manner as in Device Example-2 except that Compound 1-64 was used instead of Compound 1-48 in Device Example-2. The obtained measurement results are shown in Table 5.
- Element Example-8 An organic electroluminescent device was produced and evaluated in the same manner as in Device Example-2, except that Compound 1-65 was used instead of Compound 1-48 in Device Example-2. The obtained measurement results are shown in Table 5.
- Element reference example-4 An organic electroluminescent device was produced in the same manner as in Device Example-2, except that ETL-4 described in JP-A-2017-105717 was used instead of Compound 1-48 in Device Example-2. And evaluated. The obtained measurement results are shown in Table 5.
- Element Example-9 In device Example-1, EBL-4 is used instead of EBL-3, BD-3 is used instead of BD-2, and compound 1-67 is used instead of compound 1-48 as a cathode.
- Ytterbium, silver / magnesium (mass ratio 9/1) and silver were deposited in this order at 2 nm, 12 nm and 90 nm, respectively, in the same manner as in Device Example-1 except that they had a three-layer structure.
- An organic electroluminescent device was prepared and evaluated. Here, the film formation rate of itterbium was 0.02 nm / sec, the film formation rate of silver / magnesium was 0.5 nm / sec, and the film formation rate of silver was 0.2 nm / sec. The obtained measurement results are shown in Table 6.
- Element reference example-5 An organic electroluminescent device was produced and evaluated in the same manner as in Device Example-9, except that ETL-4 was used instead of Compound 1-67 in Device Example-9. The obtained measurement results are shown in Table 6.
- Element Example-10 In device Example-1, EBL-4 is used instead of EBL-3, BD-3 is used instead of BD-2, and ytterbium, silver / magnesium (mass ratio 9/1) and silver are used as cathodes.
- an organic electroluminescent device was produced and evaluated by the same method as in Device Example-1 except that the film was formed at 2 nm, 12 nm and 90 nm, respectively, to form a three-layer structure.
- the film formation rate of itterbium was 0.02 nm / sec
- the film formation rate of silver / magnesium was 0.5 nm / sec
- the film formation rate of silver was 0.2 nm / sec.
- the measurement results obtained are shown in Table 7.
- Element Example-11 An organic electroluminescent device was produced and evaluated in the same manner as in Device Example-10, except that Compound 1-66 was used in place of Compound 1-48 in Device Example-10. The measurement results obtained are shown in Table 7.
- Element Example-12 An organic electroluminescent device was prepared and evaluated in the same manner as in Device Example-10, except that Compound 1-62 was used instead of Compound 1-48 in Device Example-10. The measurement results obtained are shown in Table 7.
- Element comparison example-2 An organic electroluminescent device was produced and evaluated in the same manner as in Device Example-10, except that ETL-1 was used in place of Compound 1-48 in Device Example-10. The measurement results obtained are shown in Table 7.
- the cyclic azine compound (1) can provide an organic electroluminescent device having both excellent drive voltage characteristics and current efficiency characteristics as compared with conventionally known cyclic azine compounds. it can.
- the cyclic azine compound (1) according to one aspect of the present disclosure is used as an electron transport material for an organic electroluminescent device that has both excellent drive voltage characteristics and current efficiency characteristics. Further, according to the cyclic azine compound (1), it is possible to provide an organic electroluminescent device having low power consumption.
- the thin film made of the cyclic azine compound (1) according to one aspect of the present disclosure is excellent in electron transporting ability, hole blocking ability, redox resistance, water resistance, oxygen resistance, electron injection characteristics and the like, it emits organic electroluminescence. It is useful as a material for elements, as an electron transport material, a hole block material, a light emitting host material, and the like. It is especially useful when used as an electron transport material.
- the cyclic azine compound (1) since the cyclic azine compound (1) according to one aspect of the present disclosure has a wide bandgap and a high triplet excitation level, it is used not only for conventional fluorescent device applications but also for phosphorescent devices and thermal activated delayed fluorescence (1). It can be suitably used for an organic electroluminescent device using TADF).
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Abstract
Description
例えば特許文献1は、有機電界発光素子用材料として、耐熱性に優れ、駆動電圧が低く、長寿命な有機電界発光素子の提供に資する、特定の置換基を有する環状アジン化合物を開示している。
ここで、特許文献1で開示された環状アジン化合物を用いた有機電界発光素子は、優れた長寿命特性、および電流効率特性を発揮するものの、駆動電圧特性についてはさらなる改善が求められている。
さらに、本開示の他の態様は、優れた駆動電圧特性および電流効率特性を両立する有機電界発光素子を提供することに向けられている。
Ar1は、フェニル基、または4-ビフェニリル基である;
Ar2は、式(2-1)から(2-3)で示される基のいずれか1つである;
Ar31は、
水素原子、または、
式(2-1)から(2-3)で示される基のいずれか1つである。
本開示の他の態様によれば、上記環状アジン化合物を含む有機電界発光素子用電子輸送材料が提供される。
本開示の他の態様によれば、上記環状アジン化合物を含む有機電界発光素子が提供される。
本開示の他の態様によれば、優れた駆動電圧特性および電流効率特性を両立する有機電界発光素子が得られる。
本開示の一態様にかかる環状アジン化合物は、式(1)で示される:
Ar1は、フェニル基、または4-ビフェニリル基である;
Ar2は、式(2-1)から(2-3)のいずれか1つで示される基である;
Ar31は、
水素原子、または、
式(2-1)から(2-3)のいずれか1つで示される基である。
Ar2は、式(2-1)から(2-3)のいずれか1つで示される基である。
Ar3は、式(3)で示される基であり;
水素原子、または、
式(2-1)から(2-3)のいずれか1つで示される基である。
優れた駆動電圧特性および電流効率特性を両立する点で、表1~表3に示される、化合物(1-1)から(1-90)のいずれか1つで表される環状アジン化合物がより好ましい。
<有機電界発光素子用材料、有機電界発光素子用電子輸送材料>
環状アジン化合物(1)は、特に限定されるものではないが、例えば、有機電界発光素子用材料として用いることができる。また、環状アジン化合物(1)は、例えば、有機電界発光素子用電子輸送材料として用いることができる。
本開示の一態様にかかる有機電界発光素子は、環状アジン化合物(1)を含む。
有機電界発光素子の構成については特に限定されるものではないが、例えば、以下に示す(i)~(vii)の構成が挙げられる。
(i):陽極/発光層/陰極
(ii):陽極/正孔輸送層/発光層/陰極
(iii):陽極/発光層/電子輸送層/陰極
(iv):陽極/正孔輸送層/発光層/電子輸送層/陰極
(v):陽極/正孔注入層/正孔輸送層/発光層/電子輸送層/電子注入層/陰極
(vi):陽極/正孔注入層/電荷発生層/正孔輸送層/発光層/電子輸送層/陰極
(vii):陽極/正孔注入層/正孔輸送層/電子阻止層/発光層/正孔阻止層/電子輸送層/電子注入層/陰極
有機電界発光素子は、発光層、および、該発光層と陰極との間の層からなる群より選ばれる1層以上に上記式(1)で示される環状アジン化合物を含む。したがって、図1に示される構成例において有機電界発光素子100は、発光層6および電子輸送層7からなる群より選ばれる少なくとも1層に環状アジン化合物(1)を含む。特に、電子輸送層7が環状アジン化合物(1)を含むことが好ましい。
以下においては、電子輸送層7が環状アジン化合物(1)を含む有機電界発光素子100について説明する。
基板としては特に限定はなく、例えばガラス板、石英板、プラスチック板などが挙げられる。また、基板1側から発光が取り出される構成の場合、基板1は光の波長に対して透明である。
基板1上(正孔注入層3側)には陽極2が設けられている。
発光が陽極を通過して取り出される構成の有機電界発光素子の場合、陽極は当該発光を通すかまたは実質的に通す材料で形成される。
陽極上には、バッファー層(電極界面層)を設けてもよい。
陽極2と後述する発光層6との間には、陽極2側から、正孔注入層3、後述する電荷発生層4、正孔輸送層5がこの順で設けられている。
正孔注入層、正孔輸送層は、陽極より注入された正孔を発光層に伝達する機能を有し、この正孔注入層、正孔輸送層を陽極と発光層との間に介在させることによって、より低い電界で多くの正孔が発光層に注入される。
また、p型-Si、p型-SiCなどの無機化合物も正孔注入層の材料、正孔輸送層の材料の一例として挙げることができる。
正孔注入層3と正孔輸送層5との間には、電荷発生層4が設けられていてもよい。
電荷発生層の材料としては特に制限はないが、例えば、ジピラジノ[2,3-f:2’,3’-h]キノキサリン-2,3,6,7,10,11-ヘキサカルボニトリル(HAT-CN)が挙げられる。
電荷発生層は、一種または二種以上の材料からなる単層構造であってもよく、同一組成または異種組成の複数層からなる積層構造であってもよい。
正孔輸送層5と後述する電子輸送層7との間には、発光層6が設けられている。
発光層の材料としては、燐光発光材料、蛍光発光材料、熱活性化遅延蛍光発光材料が挙げられる。発光層では電子・正孔対が再結合し、その結果として発光が生じる。
発光層6と後述する陰極8との間には、電子輸送層7が設けられている。
電子輸送層は、陰極より注入された電子を発光層に伝達する機能を有する。電子輸送層を陰極と発光層との間に介在させることによって、電子がより低い電界で発光層に注入される。
電子輸送層が、発光層側を第一電子輸送層、陰極側を第二電子輸送層とする二層構造である場合、第二電子輸送層が環状アジン化合物(1)を含むことが好ましい。
電子輸送層7上には陰極8が設けられている。
陽極を通過した発光のみが取り出される構成の有機エレクトロルミネッセンス素子の場合、陰極は任意の導電性材料から形成することができる。
陰極の材料としては、ナトリウム、ナトリウム-カリウム合金、マグネシウム、リチウム、マグネシウム/銅混合物、マグネシウム/銀混合物、マグネシウム/アルミニウム混合物、マグネシウム/インジウム混合物、アルミニウム/酸化アルミニウム(Al2O3)混合物、インジウム、リチウム/アルミニウム混合物、希土類金属等が挙げられる。
陰極上(電子輸送層側)には、バッファー層(電極界面層)を設けてもよい。
以上説明した電極(陽極、陰極)を除く各層は、それぞれの層の材料(必要に応じて結着樹脂などの材料、溶剤と共に)を、例えば真空蒸着法、スピンコート法、キャスト法、LB(Langmuir-Blodgett method)法などの公知の方法によって薄膜化することにより、形成することができる。
このようにして形成された各層の膜厚については特に制限はなく、状況に応じて適宜選択することができるが、通常は5nm~5μmの範囲である。
例えば、本開示の一態様にかかる環状アジン化合物(1)は、以下に示す反応式(a)~(f)のいずれか1つで示される製法に従って合成可能であるが、これらの例により何ら限定して解釈されるものではない。
Sn(R3)3としては、Sn(Me)3、Sn(Bu)3等が例示できる。
B(OR4)2としては、B(OH)2、B(OMe)2、B(OiPr)2、B(OBu)2等が例示できる。また、2つのR4が一体となって酸素原子およびホウ素原子を含んで環を形成した場合のB(OR4)2の例としては、特に限定されるものではないが、次の(I)~(VI)で表される基が例示でき、収率がよい点で(II)で表される基が望ましい。
本開示の一態様にかかる製造方法は、式(1)で示される環状アジン化合物の製造方法であって、
式(4)で示される化合物と、式(5)で示される化合物と、を反応させることを含む:
Ar1は、フェニル基、または4-ビフェニリル基である;
Ar2は、式(2-1)から(2-3)のいずれか1つで示される基である;
水素原子、または、
式(2-1)から(2-3)のいずれか1つで示される基である;
X4は、脱離基である;
Y4は、ハロゲン原子、金属含有基、またはホウ素含有基である。
本開示の一態様にかかるピリジン化合物は、式(5)で示されるピリジン化合物である:
Ar2は、式(2-1)から(2-3)のいずれか1つで示される基である;
水素原子、または、
式(2-1)から(2-3)のいずれか1つで示される基である;
Y4は、ハロゲン原子、金属含有基、またはホウ素含有基である。
Ar2およびY4は、式(5)と同義であり;
Ar31は、式(3)と同義である。
有機電界発光素子の発光特性は、室温下、作製した素子に直流電流を印加し、輝度計(製品名:BM-9,トプコンテクノハウス社製)を用いて評価した。
1H-NMR(400MHz,CDCl3):δ9.14(dd,J=2.3,0.7Hz,1H),9.01(dd,J=1.8,1.5Hz,2H),8.86(d,J=8.9Hz,2H),8.81(d,J=6.5Hz,2H),8.02(dd,J=1.8,1.5Hz,1H),7.84-7.86(m,2H),7.83(d,J=8.6Hz,2H),7.80(d,J=8.4Hz,2H),7.72(d,J=7.1Hz,2H),7.46-7.65(m,11H),7.43(t,J=7.3Hz,1H),7.28-7.33(m,4H),7.08-7.14(m,1H),7.06(d,J=8.1Hz,1H).
1H-NMR(CDCl3):δ9.14(d,J=1.7Hz,1H),9.05(dd,J=1.5,1.5Hz,1H),9.00(dd,J=1.5,1.5Hz,1H),8.86(d,J=8.4Hz,2H),8.81(dd,J=8.2,1.7Hz,2H),8.06(dd,J=1.5,1.5Hz,1H),7.88(d,J=8.4Hz,2H),7.79-7.83(m,2H),7.82(d,J=8.2Hz,2H),7.79(d,J=8.2Hz,2H),7.72(d,J=7.3Hz,2H),7.70(d,J=7.3Hz,2H),7.59-7.63(m,3H),7.42-7.59(m,7H),7.42(dd,J=7.3,7.3Hz,1H),7.40(dd,J=7.3,7.3Hz,1H),7.26-7.38(m,5H),7.06(d,J=8.2Hz,1H).
1H-NMR(CDCl3):δ8.78-8.82(m,6H),7.91(s,1H),7.90(dd,J=8.8,0.9Hz,1H),7.83(d,J=8.8Hz,4H),7.71-7.75(m,4H),7.52(dd,J=7.6Hz,4H),7.37-7.48(m,9H),7.15(dd,J=7.6,0.9Hz,4H),6.99(t,J=3.5Hz,1H),6.94(dt,J=7.3,1.3Hz,1H),6.87(t,J=7.4Hz,1H),6.55(dd,J=8.3,1.6Hz,2H)
1H-NMR(CDCl3):δ9.13(d,J=1.8Hz,1H),9.02(dd,J=1.6,1.6Hz,1H),9.00(dd,J=1.6,1.6Hz,1H),8.86(d,J=8.4Hz,4H),8.01(dd,J=1.6,1.6Hz,1H),7.88-7.80(m,2H),7.82(d,J=8.4Hz,4H),7.80(d,J=7.2Hz,2H),7.72(d,J=7.2Hz,4H),7.56(dd,J=7.3,7.3Hz,2H),7.47-7.54(m,3H),7.51(dd,J=7.3,7.3Hz,4H),7.47(d,J=7.5Hz,1H),7.42(dd,J=7.3,7.3Hz,2H),7.26-7.36(m,5H),7.05(d,J=8.1Hz,1H).
1H-NMR(CDCl3):δ8.69-8.71(m,5H),8.62(d,J=5.0Hz,1H),8.52(t,J=1.6Hz,1H),8.36(t,J=1.6Hz,1H),7.80(d,J=8.5Hz,4H),7.72(dd,J=7.1,1.4Hz,4H),7.41-7.54(m,9H),7.21-7.39(m,12H),7.12(d,J=4.6Hz,1H).
1H-NMR(CDCl3)δ9.17(t,J=1.6Hz,1H),9.05(t,J=1.6Hz,1H),8.87(dt,J=8.6,1.8Hz,4H),8.78(dd,J=4.6,1.6Hz,2H),8.04-8.07(m,3H),7.82(dt,J=8.6,1.8Hz,4H),7.77(dd,J=4.6,1.6Hz,2H),7.71(dt,J=7.0,2.0Hz,4H),7.68(d,J=7.2Hz,1H),7.47-7.62(m,12H),7.42(tt,J=7.3,2.1Hz,2H).
1H-NMR(CDCl3):δ9.22(t,1.5Hz,1H),9.08(t,1.5Hz,1H),8.91(d,J=8.4Hz,4H),8.81(dd,J=3.1,1.5Hz,2H),8.29(s,1H),8.23(t,J=1.5Hz,1H),8.15(s,1H),8.10(t,J=8.3Hz,2H),7.98(dt,J=8.9,1.7Hz,1H),7.86(dt,J=8.3,1.9Hz,4H),7.78(t,J=6.3Hz,4H),7.73(dd,J=8.4,1.4Hz,4H)7.56-7.50(m,7H),7.46-7.41(m,3H).
1H-NMR(CDCl3):δ8.73(dd,4.8,1.7Hz,1H),7.79(dd,t.t,1.7Hz,1H),7.46(t,1.8Hz,1H),7.42-7.30(m,9H),7.27(d,1.8Hz,1H),7.25-7.24(m,2H),7.18(t,1.6Hz,1H).
1H-NMR(CDCl3):δ8.70(dd,4.8,1.7Hz,1H),7.92(dd,1.8,1.0Hz,1H),7.86(dd,7.7,1.7Hz,1H),7.79(dd,1.8,1.0Hz,1H),7.41-7.38(m,2H),7.36-7.27(m,8H),7.23-7.21(m,2H),1.36(s,12H).
1H-NMR(CDCl3):δ9.02(t,1.6Jz,1H),8.90(d、8.6Hz,4H),8.80(t、1.6Hz,1H),8.77(dd、4.7,1.7Hz,1H),8.09(dd、7.7,1.7Hz,1H),7.93(d、8.6Hz,4H),7.82(d、8.2Hz,4H),7.77(t、1.8Hz,1H),7.62-7.32(m、16H),7.29(tt、7.3,1.4Hz,1H).
1H-NMR(CDCl3)δ7.36-7.55(m,17H),7.01-7.75(m,4H),7.80-7.88(m,6H),8.79-8.84(m,5H),8.87(dd,J=1.6,1.5Hz,1H),8.93(dd,J=1.7,1.6Hz,1H).
(基板101、陽極102の用意)
陽極をその表面に備えた基板として、2mm幅の酸化インジウム-スズ(ITO)膜(膜厚110nm)がストライプ状にパターンされたITO透明電極付きガラス基板を用意した。ついで、この基板をイソプロピルアルコールで洗浄した後、オゾン紫外線洗浄にて表面処理を行った。
洗浄後の表面処理が施された基板上に、真空蒸着法で各層の真空蒸着を行い、各層を積層形成した。
まず、真空蒸着槽内に前記ガラス基板を導入し、1.0×10-4Paまで減圧した。そして、以下の順で、各層の成膜条件に従ってそれぞれ作製した。
昇華精製したHTLとNDP-9を0.15nm/秒の速度で10nm成膜し、正孔注入層103を作製した。
昇華精製したHTLを0.15nm/秒の速度で85nm成膜し、第一正孔輸送層1051を作製した。
昇華精製したEBL-3を0.15nm/秒の速度で5nm成膜し、第二正孔輸送層1052を作製した。
昇華精製したBH-1とBD-2とを95:5(質量比)の割合で20nm成膜し、発光層106を作製した。成膜速度は0.18nm/秒であった。
昇華精製したHBL-1を0.05nm/秒の速度で6nm成膜し、第一電子輸送層1071を作製した。
化合物1-48およびLiqを50:50(質量比)の割合で25nm成膜し、第二電子輸送層1072を作製した。成膜速度は0.15nm/秒であった。
最後に、基板上のITOストライプと直交するようにメタルマスクを配し、陰極108を成膜した。陰極は、銀/マグネシウム(質量比1/10)と銀とを、この順番で、それぞれ80nmと20nmとで成膜し、2層構造とした。銀/マグネシウムの成膜速度は0.5nm/秒、銀の成膜速度は成膜速度0.2nm/秒であった。
素子実施例-1において、化合物1-48代わりにETL-1を用いた以外は、素子実施例-1と同じ方法で有機電界発光素子を作製し、評価した。得られた測定結果を表4に示す。
素子実施例-1において、化合物1-48の代わりに特許文献1に記載されているETL-2を用いた以外は、素子実施例-1と同じ方法で有機電界発光素子を作製し、評価した。得られた測定結果を表4に示す。
素子実施例-1において、化合物1-48の代わりに特許文献1に記載されているETL-3を用いた以外は、素子実施例-1と同じ方法で有機電界発光素子を作製し、評価した。得られた測定結果を表4に示す。
素子実施例-1において、化合物1-48の代わりに特開2017-105717号公報に記載されているETL-4を用いた以外は、素子実施例-1と同じ方法で有機電界発光素子を作製し、評価した。得られた測定結果を表4に示す。
(基板101、陽極102の用意)
陽極をその表面に備えた基板として、2mm幅の酸化インジウム-スズ(ITO)膜(膜厚110nm)がストライプ状にパターンされたITO透明電極付きガラス基板を用意した。ついで、この基板をイソプロピルアルコールで洗浄した後、オゾン紫外線洗浄にて表面処理を行った。
洗浄後の表面処理が施された基板上に、真空蒸着法で各層の真空蒸着を行い、各層を積層形成した。
まず、真空蒸着槽内に前記ガラス基板を導入し、1.0×10-4Paまで減圧した。そして、以下の順で、各層の成膜条件に従ってそれぞれ作製した。
昇華精製したHILを0.15nm/秒の速度で50nm成膜し、正孔注入層103を作製した。
(電荷発生層104の作製)
昇華精製したHAT-CNを0.15nm/秒の速度で5nm成膜し、電荷発生層104を作製した。
昇華精製したHTLを0.15nm/秒の速度で10nm成膜し、第一正孔輸送層1051を作製した。
昇華精製したEBL-2を0.15nm/秒の速度で5nm成膜し、第二正孔輸送層1052を作製した。
昇華精製したBH-2とBD-1を95:5(質量比)の割合で25nm成膜し、発光層106を作製した。成膜速度は0.18nm/秒であった。
昇華精製したHBL-2を0.05nm/秒の速度で5nm成膜し、第一電子輸送層1071を作製した。
化合物1-48およびLiqを50:50(質量比)の割合で25nm成膜し、第二電子輸送層1072を作製した。成膜速度は0.15nm/秒であった。
最後に、基板上のITOストライプと直交するようにメタルマスクを配し、陰極108を成膜した。陰極は、銀/マグネシウム(質量比1/10)と銀とを、この順番で、それぞれ80nmと20nmとで成膜し、2層構造とした。銀/マグネシウムの成膜速度は0.5nm/秒、銀の成膜速度は成膜速度0.2nm/秒であった。
素子実施例-2において、化合物1-48の代わりに、化合物1-49を用いた以外は、素子実施例-2と同じ方法で有機電界発光素子を作製し、評価した。得られた測定結果を表5に示す。
素子実施例-2において、化合物1-48の代わりに、合成実施例-5で合成した化合物1-50を用いた以外は、素子実施例-2と同じ方法で有機電界発光素子を作製し、評価した。得られた測定結果を表5に示す。
素子実施例-2において、化合物1-48の代わりに、合成実施例-6で合成した化合物1-51を用いた以外は、素子実施例-2と同じ方法で有機電界発光素子を作製し、評価した。得られた測定結果を表5に示す。
素子実施例-2において、化合物1-48の代わりに、化合物1-52を用いた以外は、素子実施例-2と同じ方法で有機電界発光素子を作製し、評価した。得られた測定結果を表5に示す。
素子実施例-2において、化合物1-48の代わりに、化合物1-64を用いた以外は、素子実施例-2と同じ方法で有機電界発光素子を作製し、評価した。得られた測定結果を表5に示す。
素子実施例-2において、化合物1-48の代わりに、化合物1-65を用いた以外は、素子実施例-2と同じ方法で有機電界発光素子を作製し、評価した。得られた測定結果を表5に示す。
素子実施例-2において、化合物1-48の代わりに特開2017-105717号公報に記載されているETL-4を用いた以外は、素子実施例-2と同じ方法で有機電界発光素子を作製し、評価した。得られた測定結果を表5に示す。
素子実施例-1において、EBL-3の代わりに、EBL-4を用い、BD-2の代わりにBD-3を用い、化合物1-48の代わりに、化合物1-67を用い、陰極として、イッテルビウム、銀/マグネシウム(質量比9/1)と銀とを、この順番で、それぞれ2nm、12nmと90nmとで成膜し、3層構造とした以外は、素子実施例-1と同じ方法で有機電界発光素子を作製し、評価した。ここで、イッテルビウムの成膜速度は0.02nm/秒、銀/マグネシウムの成膜速度は0.5nm/秒、銀の成膜速度は成膜速度0.2nm/秒であった。得られた測定結果を表6に示す。
素子実施例-9において、化合物1-67の代わりにETL-4を用いた以外は、素子実施例-9と同じ方法で有機電界発光素子を作製し、評価した。得られた測定結果を表6に示す。
素子実施例-1において、EBL-3の代わりに、EBL-4を用い、BD-2の代わりにBD-3を用い、陰極として、イッテルビウム、銀/マグネシウム(質量比9/1)と銀とを、この順番で、それぞれ2nm、12nmと90nmとで成膜し、3層構造とした以外は、素子実施例-1と同じ方法で有機電界発光素子を作製し、評価した。ここで、イッテルビウムの成膜速度は0.02nm/秒、銀/マグネシウムの成膜速度は0.5nm/秒、銀の成膜速度は成膜速度0.2nm/秒であった。得られた測定結果を表7に示す。
素子実施例-10において、化合物1-48の代わりに化合物1-66を用いた以外は、素子実施例-10と同じ方法で有機電界発光素子を作製し、評価した。得られた測定結果を表7に示す。
素子実施例-10において、化合物1-48の代わりに化合物1-62を用いた以外は、素子実施例-10と同じ方法で有機電界発光素子を作製し、評価した。得られた測定結果を表7に示す。
素子実施例-10において、化合物1-48の代わりにETL-1を用いた以外は、素子実施例-10と同じ方法で有機電界発光素子を作製し、評価した。得られた測定結果を表7に示す。
なお、2019年7月30日に出願された日本国特許出願2019-139746号の明細書、特許請求の範囲、図面および要約書の全内容をここに引用し、本発明の明細書の開示として、取り入れるものである。
2,102 陽極
3,103 正孔注入層
4,104 電荷発生層
5,105 正孔輸送層
6,106 発光層
7,107 電子輸送層
8,108 陰極
51,1051 第一正孔輸送層
52,1052 第二正孔輸送層
71,1071 第一電子輸送層
72,1072 第二電子輸送層
100 有機電界発光素子
Claims (10)
- 請求項1から4のいずれか1項に記載の環状アジン化合物を含む有機電界発光素子用材料。
- 請求項1から4のいずれか1項に記載の環状アジン化合物を含む有機電界発光素子用電子輸送材料。
- 請求項1から4のいずれか1項に記載の環状アジン化合物を含む有機電界発光素子。
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US17/630,859 US20220274952A1 (en) | 2019-07-30 | 2020-07-22 | Cyclic azine compound, material for organic light emitting diode, electron transport material for organic light emitting diode, and organic light emitting diode |
KR1020227002856A KR20220025860A (ko) | 2019-07-30 | 2020-07-22 | 환상 아진 화합물, 유기전계 발광소자용 재료, 유기전계 발광소자용 전자수송 재료, 및 유기전계 발광소자 |
EP20846024.6A EP4006023A4 (en) | 2019-07-30 | 2020-07-22 | CYCLIC AZINE COMPOUND, ORGANIC ELECTROLUMINescent ELEMENT MATERIAL, ELECTRON TRANSPORT MATERIAL FOR ORGANIC ELECTROLUMINescent ELEMENT, AND ORGANIC ELECTROLUMINescent ELEMENT |
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