WO2023115394A1 - 双芳胺化合物及其用途、光取出材料、电致发光器件和显示装置 - Google Patents

双芳胺化合物及其用途、光取出材料、电致发光器件和显示装置 Download PDF

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WO2023115394A1
WO2023115394A1 PCT/CN2021/140537 CN2021140537W WO2023115394A1 WO 2023115394 A1 WO2023115394 A1 WO 2023115394A1 CN 2021140537 W CN2021140537 W CN 2021140537W WO 2023115394 A1 WO2023115394 A1 WO 2023115394A1
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陈磊
王丹
梁丙炎
陈雪芹
张东旭
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京东方科技集团股份有限公司
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Priority to CN202180004119.4A priority Critical patent/CN116783172A/zh
Priority to US18/273,262 priority patent/US20240315129A1/en
Priority to PCT/CN2021/140537 priority patent/WO2023115394A1/zh
Publication of WO2023115394A1 publication Critical patent/WO2023115394A1/zh

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Definitions

  • the embodiments of the present disclosure relate to but are not limited to the field of display technology, in particular to a bisarylamine compound and its application, light extraction material, electroluminescent device and display device.
  • OLED Organic Light Emitting Device
  • An OLED device consists of a light-emitting layer and a pair of electrodes located on both sides of the light-emitting layer. When an electric field is applied between the two electrodes, electrons are injected from the negative electrode and holes are injected from the positive electrode. In the light-emitting layer, the electrons and holes recombine to form an excited state. When the excited state returns to the ground state, the energy generated will emit light. . Due to the characteristics of active light emission, high luminous brightness and efficiency, high resolution, wide color gamut and viewing angle, fast response speed, low energy consumption and flexibility, OLED devices have become the hottest mainstream display products in the market.
  • the light extraction layer (also known as the capping layer, CPL) material can effectively improve the light extraction efficiency of the OLED device.
  • the light extraction layer in the OLED device can be a layer of organic or inorganic transparent material with a relatively high refractive index, and the absorption intensity in the visible light range is low and close to none.
  • the embodiment of the present disclosure provides a bisarylamine compound, the general structural formula of which is:
  • At least two of Ar 1 to Ar 4 include groups represented by general formula II and/or III:
  • Ar 1 to Ar 4 excluding groups represented by general formula II or III, including substituted or unsubstituted C6 to C60 aryl groups, substituted or unsubstituted C5 to C60 heteroaryl groups;
  • substituted C6 to C60 aryl, substituted C5 to C60 heteroaryl means substituted by one or more of the following groups: deuterium, halogen, nitro, nitrile, C1 to C30 alkyl , C2 to C30 alkenyl, C1 to C30 alkoxy, C1 to C30 thioether group, C6 to C60 aryl and C5 to C60 heteroaryl;
  • X 1 includes CR 3 R 4 , O, NR 5 or S;
  • X 2 includes O or S;
  • R 1 to R 5 each independently include hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C2 to C30 alkenyl, substituted or unsubstituted Any one of C1 to C30 alkoxy, substituted or unsubstituted C1 to C30 thioether group, substituted or unsubstituted C6 to C50 aryl, substituted or unsubstituted C2 to C50 heteroaryl species, and when R 1 and R 2 each independently include a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heteroaryl group, R 1 or R 2 and the general formula II or
  • the benzene rings in III are connected by a single bond or fused by sharing two atoms; here, substituted C1 to C30 alkyl, substituted C2 to C30 alkeny
  • L 1 to L 4 each independently include any one of a single bond, a substituted or unsubstituted C6 to C50 arylene group, a substituted or unsubstituted C2 to C50 heteroarylene group, and here, the substituted C6 to C50 heteroarylene group C50 arylene group, substituted C2 to C50 heteroarylene group means substituted by one or more of the following groups: deuterium, halogen, nitro, nitrile, C6 to C50 aryl, C2 to C50 the heteroaryl;
  • a and bond L form a five-membered ring, and A includes any one of O, S, NR 6 , CR 7 R 8 ;
  • At least one of Ar 1 to Ar 4 includes a group represented by general formula IV or V:
  • At least one of Ar 1 to Ar 4 includes a group shown in general formula VI:
  • Y 1 and Z 1 each independently include any one of CR 12 R 13 , O, NR 14 , and S, each of Y 2 and Z 2 independently includes C or N, and both Y 3 and Z 3 include N;
  • substituted C6 to C60 aryl, substituted or unsubstituted C5 to C60 heteroaryl that does not include groups shown in general formulas IV, V, and VI in Ar 1 to Ar 4 Species;
  • substituted C6 to C60 aryl, substituted C5 to C60 heteroaryl means substituted by one or more of the following groups: deuterium, halogen, nitro, nitrile, C1 to C30 Alkyl, C2 to C30 alkenyl, C1 to C30 alkoxy, C1 to C30 thioether, C6 to C60 aryl and C5 to C60 heteroaryl;
  • R 6 to R 14 each independently include hydrogen, heavy hydrogen, halogen, nitro, nitrile, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C2 to C30 alkenyl, substituted or unsubstituted Any one of C1 to C30 alkoxy, substituted or unsubstituted C1 to C30 thioether group, substituted or unsubstituted C6 to C50 aryl, substituted or unsubstituted C2 to C50 heteroaryl Species;
  • Substituted C2 to C50 heteroaryl refers to being substituted by one or more of the following groups: deuterium, halogen, nitro, nitrile, C1 to C30 alkyl
  • L 1 and L 2 each independently include a single bond, substituted or unsubstituted C6 to C50 arylene, substituted or unsubstituted C2 to C50 heteroarylene, here, the substituted C6 to C50 C50 arylene group, substituted C2 to C50 heteroarylene group means substituted by one or more of the following groups: deuterium, halogen, nitro, nitrile, C6 to C50 aryl, C2 to C50 The heteroaryl.
  • Embodiments of the present disclosure also provide the use of the above-mentioned bisarylamine compound as a light extraction material.
  • Embodiments of the present disclosure also provide light extraction materials, including the above-mentioned bisarylamine compound.
  • An embodiment of the present disclosure also provides an electroluminescent device, comprising the above-mentioned bisarylamine compound.
  • An embodiment of the present disclosure also provides a display device, including the above-mentioned electroluminescent device.
  • FIG. 1 is a schematic structural view of an electroluminescent device according to an exemplary embodiment of the present disclosure.
  • the embodiment of the present disclosure provides a bisarylamine compound, the general structural formula of which is:
  • At least two of Ar 1 to Ar 4 include groups represented by general formula II and/or III:
  • Ar 1 to Ar 4 excluding groups represented by general formula II or III, including substituted or unsubstituted C6 to C60 aryl groups, substituted or unsubstituted C5 to C60 heteroaryl groups;
  • substituted C6 to C60 aryl, substituted C5 to C60 heteroaryl means substituted by one or more of the following groups: deuterium, halogen, nitro, nitrile, C1 to C30 alkyl , C2 to C30 alkenyl, C1 to C30 alkoxy, C1 to C30 thioether group, C6 to C60 aryl and C5 to C60 heteroaryl;
  • X 1 includes CR 3 R 4 , O, NR 5 or S;
  • X 2 includes O or S;
  • R 1 to R 5 each independently include hydrogen, deuterium, halogen, nitro, nitrile, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C2 to C30 alkenyl, substituted or unsubstituted Any one of C1 to C30 alkoxy, substituted or unsubstituted C1 to C30 thioether group, substituted or unsubstituted C6 to C50 aryl, substituted or unsubstituted C2 to C50 heteroaryl species, and when R 1 and R 2 each independently include a substituted or unsubstituted C6 to C50 aryl group, a substituted or unsubstituted C2 to C50 heteroaryl group, R 1 or R 2 and the general formula II or
  • the benzene rings in III are connected by a single bond or fused by sharing two atoms; here, substituted C1 to C30 alkyl, substituted C2 to C30 alkeny
  • L 1 to L 4 each independently include any one of a single bond, a substituted or unsubstituted C6 to C50 arylene group, a substituted or unsubstituted C2 to C50 heteroarylene group, and here, the substituted C6 to C50 heteroarylene group C50 arylene group, substituted C2 to C50 heteroarylene group means substituted by one or more of the following groups: deuterium, halogen, nitro, nitrile, C6 to C50 aryl, C2 to C50 the heteroaryl;
  • a and bond L form a five-membered ring, and A is any one of O, S, NR 6 , CR 7 R 8 ;
  • At least one of Ar 1 to Ar 4 includes a group represented by general formula IV or V:
  • At least one of Ar 1 to Ar 4 includes a group shown in general formula VI:
  • Y 1 and Z 1 each independently include any one of CR 12 R 13 , O, NR 14 , and S, each of Y 2 and Z 2 independently includes C or N, and both Y 3 and Z 3 include N;
  • substituted C6 to C60 aryl, substituted or unsubstituted C5 to C60 heteroaryl that does not include groups shown in general formulas IV, V, and VI in Ar 1 to Ar 4 Species;
  • substituted C6 to C60 aryl, substituted C5 to C60 heteroaryl means substituted by one or more of the following groups: deuterium, halogen, nitro, nitrile, C1 to C30 Alkyl, C2 to C30 alkenyl, C1 to C30 alkoxy, C1 to C30 thioether, C6 to C60 aryl and C5 to C60 heteroaryl;
  • R 6 to R 14 each independently include hydrogen, heavy hydrogen, halogen, nitro, nitrile, substituted or unsubstituted C1 to C30 alkyl, substituted or unsubstituted C2 to C30 alkenyl, substituted or unsubstituted Any one of C1 to C30 alkoxy, substituted or unsubstituted C1 to C30 thioether group, substituted or unsubstituted C6 to C50 aryl, substituted or unsubstituted C2 to C50 heteroaryl Species;
  • Substituted C2 to C50 heteroaryl refers to being substituted by one or more of the following groups: deuterium, halogen, nitro, nitrile, C1 to C30 alkyl
  • L 1 and L 2 each independently include a single bond, substituted or unsubstituted C6 to C50 arylene, substituted or unsubstituted C2 to C50 heteroarylene, here, the substituted C6 to C50 C50 arylene group, substituted C2 to C50 heteroarylene group means substituted by one or more of the following groups: deuterium, halogen, nitro, nitrile, C6 to C50 aryl, C2 to C50 The heteroaryl.
  • the group represented by the general formula II may include any one of the following groups:
  • the group represented by the general formula II may include any one of the following groups:
  • the group represented by the general formula IV may include:
  • At least one of Ar 1 to Ar 4 includes a group represented by the general formula IV-1.
  • the group represented by the general formula V may include:
  • At least one of Ar 1 to Ar 4 includes a group represented by the general formula V-1.
  • the five-membered ring contains three N atoms; the existence of multiple N atoms increases the electron cloud density between the lone pair of electrons, and the conjugation Moreover, the N atom forms a hydrogen bond with the H on the adjacent benzene ring, increasing the planar type of the two aromatic rings, increasing the polarizability of the fragment, and the N-substituted heterocycle relative to other positions, the general formula IV-1
  • the conjugation and planarity of the group represented by the general formula V-1 are better.
  • the group represented by the general formula IV may include:
  • Groups represented by general formula V may include:
  • At least one of Ar 1 to Ar 4 includes a group represented by the general formula IV-2 or V-2.
  • the group shown in general formula IV-2 can include:
  • the group represented by the general formula V-2 may include:
  • the bisarylamine compound may include any one of the following compounds:
  • the refractive index of the bisarylamine compound at a wavelength of 460nm may be in the range of 2.08 to 2.25;
  • the refractive index of the arylamine compound at a wavelength of 530nm may be in the range of 1.92 to 2.16;
  • the refractive index of the aromatic amine compound at a wavelength of 620nm may be in the range of 1.88 to 2.07.
  • the absorption coefficient of the bisarylamine compound at a wavelength of 400nm may be above 0.84, and the absorption coefficient at a wavelength of 450nm or greater than 450nm is 0.
  • the glass transition temperature of the bisarylamine compound may be above 127°C.
  • the embodiment of the present disclosure also provides the use of the above-mentioned bisarylamine compound as a light extraction material.
  • An embodiment of the present disclosure also provides a light extraction material, which includes the above-mentioned bisarylamine compound.
  • An embodiment of the present disclosure also provides an electroluminescent device, which includes the above-mentioned bisarylamine compound.
  • the electroluminescence device includes a light extraction layer, and a material of the light extraction layer may include the bisarylamine compound as described above.
  • the electroluminescent device may include: an anode, a hole injection layer (Hole Injection Layer, HIL), a hole transport layer (Hole Transport Layer, HTL), an electron blocking layer (Electron Block Layer, EBL), light emitting layer (Emitting Layer, EML), hole blocking layer (Hole Block Layer, HBL), electron transport layer (Electron Transport Layer, ETL), electron injection layer (Electron Injection Layer, EIL), cathode and light extraction layer .
  • HIL hole injection layer
  • HTL hole transport layer
  • EBL electron blocking layer
  • EML light emitting layer
  • Hole Block Layer HBL
  • ETL electron transport layer
  • EIL Electrode and light extraction layer
  • FIG. 1 is a schematic structural view of an electroluminescent device according to an exemplary embodiment of the present disclosure.
  • the electroluminescent device may include: an anode 100, a hole injection layer 200, a hole transport layer 300, an electron blocking layer 400, a light emitting layer 500, a hole blocking layer 600, an electron transport layer 700, Electron injection layer 800 , cathode 900 and light extraction layer 1000 .
  • the hole injection layer 200 is disposed on the surface of the anode 100 side
  • the hole transport layer 300 is disposed on the surface of the hole injection layer 200 away from the anode 100 side
  • the blocking layer 400 is disposed on the surface of the hole transport layer 300 on the side away from the anode 100
  • the light-emitting layer 500 is disposed on the surface of the electron blocking layer 400 on the side away from the anode 100
  • the hole blocking layer 600 is arranged on the surface of the luminescent layer 500 away from the anode 100
  • the electron transport layer 700 is arranged on the surface of the hole blocking layer 600 away from the anode 100.
  • the electron injection layer 800 is arranged on the surface of the electron transport layer 700 away from the anode 100, and the cathode 900 is arranged on the surface of the electron injection layer 800 away from the anode 100.
  • the light extraction layer 1000 is disposed on the surface of the cathode 900 away from the anode 100 .
  • the light extraction layer may be formed by vapor deposition of the light extraction material provided in the embodiments of the present disclosure.
  • the anode may be a material having a high work function.
  • the anode can be made of a transparent oxide material, such as indium tin oxide (ITO) or indium zinc oxide (Indium Zinc Oxide, IZO).
  • ITO indium tin oxide
  • IZO indium zinc oxide
  • the anode can use a composite structure of metal and transparent oxide, such as Ag/ITO (Indium Tin Oxide, Indium Tin Oxide), Ag/IZO (Indium Zinc Oxide, Indium Zinc Oxide), Al/ITO , Al/IZO or ITO/Ag/ITO, etc., can ensure good reflectivity.
  • the material of the hole injection layer may include a transition metal oxide, for example, may include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, Any one or more of zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, and manganese oxide.
  • a transition metal oxide for example, may include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, Any one or more of zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, and manganese oxide.
  • the material of the hole injection layer may include a p-type dopant of a strong electron-withdrawing system and a hole transport material;
  • the p-type dopant may include 2,3,6,7,10,11-hexacyano-1,4,5,8,9,12-hexaazatriphenylene, 2,3,5, 6-tetrafluoro-7,7',8,8'-tetracyano-p-benzoquinone (F4TCNQ), 1,2,3-tris[(cyano)(4-cyano-2,3,5,6 - any one or more of tetrafluorophenyl) methylene] cyclopropane;
  • the hole transport material may include any one or more of arylamine hole transport materials, dimethylfluorene hole transport materials, and carbazole hole transport materials; for example, the hole transport material May include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-bis(3-methylphenyl)-N,N'- Diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (BAFLP ), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (DFLDPBi), 4,4'-bis(9-carbazolyl ) biphenyl (CBP) and any one or more of 9-phenyl-3-[4-(10-phenyl-9-
  • the hole injection layer may be formed by evaporation.
  • the material of the hole transport layer may include any one or more of arylamine-based hole-transport materials, dimethylfluorene-based hole-transport materials, and carbazole-based hole-transport materials ;
  • the material of the hole transport layer may include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-bis(3- Methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4-phenyl-4'-(9-phenylfluorene -9-yl)triphenylamine (BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (DFLDPBi), 4 ,4'-bis(9-carbazolyl)biphenyl (NPB), N,N
  • the hole transport layer may be formed by evaporation.
  • the material of the electron blocking layer may include any one or more of arylamine-based electron-blocking materials, dimethylfluorene-based electron-blocking materials, and carbazole-based electron-blocking materials; for example, the The material of the electron blocking layer may include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB), N,N'-bis(3-methylphenyl) -N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl) Triphenylamine (BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (DFLDPBi), 4,4'-bis Any of (9-carbazolyl)biphenyl (CBP)
  • the electron blocking layer may be formed by evaporation.
  • the material of the light-emitting layer may include one kind of light-emitting material, or two or more kinds of light-emitting materials.
  • a host luminescent material and a guest luminescent material doped into the host luminescent material may be included.
  • the electroluminescent device may be a blue electroluminescent device, a green electroluminescent device or a red electroluminescent device, and the material of the light-emitting layer of the blue electroluminescent device includes blue As for the luminescent material, the material of the luminescent layer of the green electroluminescent device includes a green luminescent material, and the material of the luminescent layer of the red electroluminescent device may include a red luminescent material.
  • the blue light-emitting material may include a pyrene derivative-based blue light-emitting material, an anthracene derivative-based blue light-emitting material, a fluorene derivative-based blue light-emitting material, a perylene derivative-based blue light-emitting material Any one or more of styrylamine derivative-based blue luminescent materials and metal complex-based blue luminescent materials.
  • the blue light-emitting material may include N1, N6-bis([1,1'-biphenyl]-2-yl)-N1,N6-bis([1,1'-biphenyl]-4-yl ) pyrene-1,6-diamine, 9,10-di-(2-naphthyl)anthracene (ADN), 2-methyl-9,10-di-2-naphthylanthracene (MADN), 2,5 ,8,11-Tetra-tert-butylperylene (TBPe), 4,4'-bis[4-(diphenylamino)styryl]biphenyl (BDAV Bi), 4,4'-bis[4-(bis Any one or more of p-tolylamino)styryl]biphenyl (DPAVBi), bis(4,6-difluorophenylpyridine-C2,N)pyridinecarboyl iridium (FIrpic).
  • ADN
  • the green luminescent material may include coumarin dyes, quinacridine copper derivative-based green luminescent materials, polycyclic aromatic hydrocarbon-based green luminescent materials, diamine anthracene derivative-based green luminescent materials, carba Any one or more of azole derivative-based green luminescent materials and metal complex-based green luminescent materials.
  • the green luminescent material may include coumarin 6 (C-6), coumarin 545T (C-525T), quinacridone copper (QA), N,N'-dimethylquinacridone (DMQA), 5,12-diphenylnaphthonaphthalene (DPT), N10,N10'-diphenyl-N10,N10'-diphthaloyl-9,9'-dianthracene-10,10'- Diamine (abbreviation: BA-NPB), tris(8-hydroxyquinoline) aluminum (III) (abbreviation: Alq3), tris(2-phenylpyridine) iridium (Ir(ppy)3), acetylacetonate Any one or more of bis(2-phenylpyridine)iridium (Ir(ppy)2(acac)).
  • C-6 coumarin 6
  • DMQA quinacridone copper
  • DMQA N,N'-dimethylquinacridone
  • DPT 5,12-dipheny
  • the red luminescent material may include any one or more of DCM-based red luminescent materials and metal complex-based red luminescent materials.
  • the red luminescent material may include 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran (DCM), 4-( Dicyanomethylene)-2-tert-butyl-6-(1,1,7,7-tetramethyljulonidin-9-enyl)-4H-pyran (DCJTB), bis(1- Phenylisoquinoline)(acetylacetonate)iridium(III)(Ir(piq)2(acac)), platinum octaethylporphyrin (abbreviation: PtOEP), bis(2-(2'-benzothienyl) Any one or more of pyridine-N,C3')(acetylacetonate)iridium (abbreviation: Ir(btp)2(acac).
  • DCM dimethyl-6-(4-dimethylaminostyryl)-4H-pyran
  • DCJTB 4-( D
  • the light emitting layer may be formed by evaporation.
  • the material of the hole blocking layer may include aromatic heterocyclic hole blocking materials, for example, may include benzimidazole and its derivatives, imidazopyridine and its derivatives.
  • the material of the hole blocking layer may include 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), 1, 3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (OXD-7), 3-(4-tert-butylphenyl)-4- Phenyl-5-(4-biphenyl)-1,2,4-triazole (TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5- (4-biphenyl)-1,2,4-triazole (p-EtTAZ), bathophenanthroline (BPhen), (BCP), 4,4'-bis(5-methylbenzoxazole- Any one or more of 2-yl) stilbenes (BzOs).
  • PBD 2-(4-biphenyl)-5-(4-tert
  • the hole blocking layer may be formed by evaporation.
  • the material of the electron transport layer may include aromatic heterocyclic electron transport materials, for example, may include benzimidazole and its derivatives electron transport materials, imidazopyridine and its derivatives electron transport materials.
  • Transport materials benzimidazolophenanthridine derivatives electron transport materials, pyrimidine and its derivatives electron transport materials, triazine derivatives electron transport materials, pyridine and its derivatives electron transport materials, pyrazine and its derivatives
  • Species electron transport materials quinoxaline and its derivatives electron transport materials, oxadiazole and its derivatives electron transport materials, quinoline and its derivatives electron transport materials, isoquinoline derivatives electron transport materials,
  • Electron transport materials based on phenanthroline derivatives electron transport materials based on diazaphosphoroles, electron transport materials based on phosphine oxides, electron transport materials based on aromatic ketones, electron transport materials based on lactams, and boranes any one or more of the materials.
  • the material of the electron transport layer may include 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (PBD), 1,3 -Bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (OXD-7), 3-(4-tert-butylphenyl)-4-benzene Base-5-(4-biphenyl)-1,2,4-triazole (TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-( 4-biphenyl)-1,2,4-triazole (p-EtTAZ), bathophenanthroline (BPhen), (BCP), 4,4'-bis(5-methylbenzoxazole-2 - any one or more of stilbene (BzOs).
  • PBD 2-(4-biphenyl)-5-(4-tert
  • the electron transport layer may be formed by evaporation.
  • the material of the electron injection layer may include any one or more of an alkali metal electron injection material and a metal electron injection material.
  • the electron injection layer material may include any one or more of LiF, Yb, Mg, and Ca.
  • the electron injection layer may be formed by evaporation.
  • the cathode may be formed using a metal with a low work function such as Al, Ag, Mg, or an alloy containing a metal material with a low work function.
  • An embodiment of the present disclosure also provides a display device, the display device comprising the electroluminescence device as described above.
  • the display device may include a plurality of the electroluminescent devices.
  • the electroluminescent device may be a blue electroluminescent device, a green electroluminescent device or a red electroluminescent device, and the display device may include a blue electroluminescent device, a green electroluminescent device and a red electroluminescent device.
  • Luminescent devices may be a blue electroluminescent device, a green electroluminescent device and a red electroluminescent device.
  • the display device can be any product or component with a display function such as a mobile phone, a tablet computer, a television, a monitor, a notebook computer, a digital photo frame, a navigator, a vehicle display, a smart watch, and a smart bracelet.
  • a display function such as a mobile phone, a tablet computer, a television, a monitor, a notebook computer, a digital photo frame, a navigator, a vehicle display, a smart watch, and a smart bracelet.
  • the synthesis method of the exemplary bisarylamine compound of the present disclosure is as follows.
  • the synthetic process of intermediate A3 is similar to the synthetic process of intermediate A2 in Synthetic Example 1, but the raw material 4-(benzo [D] oxazol-2-yl) aniline is replaced by 2-amino-benzoxazole, other The steps are the same, and the yield is 83%.
  • the synthesis process of compound 2 is similar to the synthesis process of compound 1 in synthesis example 1, but intermediate A2 is replaced by intermediate A3, and the yield is 76%.
  • the synthesis process of intermediate A4 is similar to the synthesis process of intermediate A3 in Synthesis Example 2, but the raw material bromobenzene is replaced with 4-bromobiphenyl, other steps are the same, and the yield is 73%.
  • the synthesis process of intermediate E is similar to the synthesis process of intermediate A3 in Synthesis Example 2, but the raw material bromobenzene is replaced by 2-bromonaphthalene, other steps are the same, and the yield is 88%.
  • the synthesis process of compound 5 is similar to the synthesis process of compound 2 in synthesis example 2, but intermediate A3 is replaced by intermediate E, and the yield is 70%.
  • the synthesis process of intermediate A6 is similar to the synthesis process of intermediate A2 in Synthesis Example 1, but the raw material bromobenzene is replaced with 2-bromo(9-phenyl)carbazole, other steps are the same, and the yield is 71%.
  • the synthesis process of intermediate A7 is similar to the synthesis process of intermediate A2 in Synthesis Example 1, but the raw material 4-(benzo[D]oxazol-2-yl)aniline is replaced by 4-(2-benzothiazolyl) Aniline, the other steps are the same, the yield is 80%.
  • the synthesis process of intermediate A8 is similar to the synthesis process of intermediate A7 in Synthesis Example 6, but the raw material 4-(2-benzothiazolyl)aniline is replaced by 4-(1-phenylbenzimidazol-2-yl) Aniline, and changing bromobenzene to 4-bromobiphenyl, the other steps are the same, and the yield is 65%.
  • the refractive index is measured by ellipsometer; the scanning range of the instrument is 245nm to 1000nm; a thin film of the compound is formed by evaporation on a silicon wafer, and the thickness of the film is 50nm, and then the refractive index is measured.
  • CP1 is following compound:
  • the compounds of the examples of the present disclosure have higher refractive indices at different wavelengths.
  • the refractive index is an important physical parameter of the light extraction material, and the refractive index directly determines the optical coupling efficiency of the device. Therefore, the compound of the disclosed embodiment is suitable as a light extraction material, which can significantly improve the light extraction efficiency of the device, obtain a higher external quantum efficiency, reduce the loss of light inside the device, and further improve the efficiency of the device.
  • a film containing the bisarylamine compound is formed by vapor deposition on a glass substrate, and the thickness of the film is 50 nm, and then the absorption coefficient is tested by an ultraviolet-visible absorption spectrometer.
  • CPL materials In order to protect OLED devices from the damage of ultraviolet light in the external environment, CPL materials need to have a strong absorption capacity around 400nm to absorb external ultraviolet light and prevent device aging. At the same time, it cannot absorb the light emitted by the OLED device itself, so the absorption at 450nm and beyond must be almost zero.
  • the compounds of the embodiments of the present disclosure have a significantly higher absorption coefficient at a wavelength of 400nm, so they can better absorb ultraviolet light;
  • the absorption at the place is zero, and the absorption at the wavelength greater than 450nm is also zero (not shown in the table), indicating that the light emitted by the device itself will not be absorbed.
  • the measuring instrument of the glass transition temperature is a DSC differential scanning calorimeter; the test atmosphere is nitrogen, the heating rate is 10°C/min, and the temperature range is 50°C to 300°C; the measured glass transition temperature (Tg) is as follows Table 3 shows.
  • the glass transition temperature (Tg) determines the thermal stability of the material in evaporation. The higher the Tg, the better the thermal stability of the material. Generally, a Tg above 110°C can meet the requirements of evaporation. It can be seen that the glass transition temperatures Tg of the compounds in the examples of the present disclosure are all relatively high, all above 120°C. Therefore, the compound of the embodiment of the present disclosure is suitable as a light extraction material, and has good stability in the evaporation process, which can solve the problem of more decomposed impurities caused by heating and unstable materials in the evaporation process, and is conducive to improving The stability of the material in the device and the lifetime of the device.
  • the preparation process of the OLED device includes: cleaning and drying the pre-prepared ITO substrate; sequentially evaporating HIL material, HTL material, and EBL material on the anode; then evaporating the light-emitting layer material; evaporating the HBL material on the light-emitting layer , ETL material, EIL material; after that, the cathode is evaporated; on the cathode, the compound of the disclosed embodiment is evaporated to form a CPL layer.
  • the device is packaged in glass UV.
  • Thin-Film Encapsulation (TFE) can also be used, but LIF or organic materials with a refractive index n ⁇ 1.6 need to be deposited on the CPL.
  • the material of the CPL layer is selected from Compound 1 to Compound 38 provided in the examples of the present disclosure.
  • ITO/m-MTDATA:F4TCNQ 3%10nm/m-MTDATA 100nm/CBP 75nm/RH:RD 3%45nm/TPBI 5nm/BCP:Liq 1:1 30nm/Yb 1nm/Mg:Ag 13nm/CPL 60nm
  • the performance of the first blue OLED device is shown in Table 5.
  • the blue OLED devices prepared by using the compounds of the embodiments of the present disclosure as CPL materials have higher light extraction efficiency (EQE) and better stability , efficiency and lifespan have been improved.
  • the light extraction efficiency trends of red OLED devices and green OLED devices are similar to those of blue OLED devices. Therefore, using the high refractive index compound of the embodiment of the present disclosure as the CPL material of the OLED device can improve the light extraction efficiency of the OLED device. Furthermore, due to the improvement of the thermal stability of the CPL material, the service life of the device is relatively improved.
  • the material of the CPL layer is selected from Compound 1' to Compound 69' provided in the examples of the present disclosure.
  • ITO/m-MTDATA:F4TCNQ 3%10nm/m-MTDATA 100nm/CBP 75nm/RH:RD 3%45nm/TPBI 5nm/BCP:Liq 1:1 30nm/Yb 1nm/Mg:Ag 13nm/CPL 65nm
  • the performance of the second blue OLED device is shown in Table 6.
  • the performance of the second green OLED device is shown in Table 7.
  • the performance of the second red OLED device is shown in Table 8.
  • the light extraction efficiency (EQE) of the device prepared by using the bisarylamine compound of the embodiment of the present disclosure as the CPL material is higher, and the stability is improved to a certain extent. Lift, efficiency and longevity have all been improved.

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Abstract

一种双芳胺化合物及其用途、光取出材料、电致发光器件和显示装置，所述双芳胺化合物的结构通式为式(I)。

Description

双芳胺化合物及其用途、光取出材料、电致发光器件和显示装置 技术领域
本公开实施例涉及但不限于显示技术领域，尤其涉及一种双芳胺化合物及其用途、光取出材料、电致发光器件和显示装置。
背景技术
近年来，有机电致发光器件(Organic Light Emitting Device，OLED)作为一种新型的平板显示逐渐受到更多的关注。OLED器件由发光层和位于发光层两侧的一对电极所构成。当在两个电极之间施加电场时，电子由负极注入，空穴由正极注入，在发光层中电子和空穴重新结合形成激发态，当激发态返回到基态时产生的能量就会发射光。OLED器件由于具有主动发光、发光亮度与效率高、分辨率高、色域与视角宽、响应速度快、低能耗以及可柔性化等特点，成为目前市场上炙手可热的主流显示产品。
近几年，OLED器件的应用领域已经从手机延伸到其它高质量的信息显示装置，随着产品种类不断的发展，及各类显示装置的要求，对OLED器件的需求越来越高，需要开发更高的分辨率、更高效率、更低电压、更长寿命的器件。在对OLED器件性能的提升与优化过程中，可以通过改善器件中不同功能层及其组合来实现。
光在不同介质之间传输时，由于折射率差异，会在介质接触面发生损失。其中光取出层(又叫覆盖层，Capping Layer,CPL)材料可以有效地提高OLED器件的出光效率。光取出层在OLED器件中可以为一层折射率较高的有机或无机透明材料，在可见光范围内吸收强度较低接近于无。通过在OLED器件中引入光取出层，可以明显提高器件的外量子效率，减少光在器件内部的损耗，进而提高器件效率；而且，光取出层可以吸收紫外光，从而可以避免紫外线对器件稳定性的影响。
发明内容
以下是对本文详细描述的主题的概述。本概述并非是为了限制本申请的保护范围。
本公开实施例提供一种双芳胺化合物，其结构通式为：
Figure PCTCN2021140537-appb-000001
其中，A不存在或存在；
i)当A不存在时，萘环与苯环通过键L连接；
Ar 1至Ar 4中的至少两个包括通式II和/或III所示的基团：
Figure PCTCN2021140537-appb-000002
Ar 1至Ar 4中不包括通式II或III所示的基团的包括取代或未取代的C6至C60的芳基、取代或未取代的C5至C60的杂芳基中的任意一种；这里，取代的C6至C60的芳基、取代的C5至C60的杂芳基是指被一个或多个如下基团所取代：重氢、卤素、硝基、腈基、C1至C30的烷基、C2至C30的烯基、C1至C30的烷氧基、C1至C30的硫醚基、C6至C60的芳基和C5至C60的杂芳基；
X 1包括CR 3R 4、O、NR 5或S；X 2包括O或S；
R 1至R 5各自独立地包括氢、重氢、卤素、硝基、腈基、取代或未取代的C1至C30的烷基、取代或未取代的C2至C30的烯基、取代或未取代的C1至C30的烷氧基、取代或未取代的C1至C30的硫醚基、取代或未取代的C6至C50的芳基、取代或未取代的C2至C50的杂芳基中的任意一种，并且 当R 1、R 2各自独立地包括取代或未取代的C6至C50的芳基、取代或未取代的C2至C50的杂芳基时，R 1或R 2分别与通式II或III中的苯环通过单键连接或通过共用两个原子的方式稠合连接；这里，取代的C1至C30的烷基、取代的C2至C30的烯基、取代的C1至C30的烷氧基、取代的C1至C30的硫醚基、取代的C6至C50的芳基、取代的C2至C50的杂芳基是指被一个或多个如下基团所取代：重氢、卤素、硝基、腈基、C1至C30的烷基、C2至C30的烯基、C1至C30的烷氧基、C1至C30的硫醚基、C6至C50的芳基、C2至C50的杂芳基；
L 1至L 4各自独立地包括单键、取代或未取代的C6至C50的亚芳基、取代或未取代的C2至C50的亚杂芳基中的任意一种，这里，取代的C6至C50的亚芳基、取代的C2至C50的亚杂芳基是指被一个或多个如下基团所取代：重氢、卤素、硝基、腈基、C6至C50的芳基、C2至C50的杂芳基；
ii)当A存在时，A与键L形成五元环，A包括O、S、NR 6、CR 7R 8中的任意一种；
Ar 1至Ar 4中的至少一个包括通式IV或V所示的基团：
Figure PCTCN2021140537-appb-000003
并且Ar 1至Ar 4中的至少一个包括通式VI所示的基团：
Figure PCTCN2021140537-appb-000004
Y 1、Z 1各自独立地包括CR 12R 13、O、NR 14、S中的任意一种，Y 2、Z 2各自独立地包括C或N，Y 3、Z 3均包括N；
Ar 1至Ar 4中不包括通式IV、V、VI所示的基团的包括取代或未取代的C6至C60的芳基、取代或未取代的C5至C60的杂芳基中的任意一种；这里，取代的C6至C60的芳基、取代的C5至C60的杂芳基是指被一个或多个如下基团所取代：重氢、卤素、硝基、腈基、C1至C30的烷基、C2至C30的烯基、C1至C30的烷氧基、C1至C30的硫醚基、C6至C60的芳基和C5至C60的杂芳基；
R 6至R 14各自独立地包括氢、重氢、卤素、硝基、腈基、取代或未取代的C1至C30的烷基、取代或未取代的C2至C30的烯基、取代或未取代的C1至C30的烷氧基、取代或未取代的C1至C30的硫醚基、取代或未取代的C6至C50的芳基、取代或未取代的C2至C50的杂芳基中的任意一种；这里，取代的C1至C30的烷基、取代的C2至C30的烯基、取代的C1至C30的烷氧基、取代的C1至C30的硫醚基、取代的C6至C50的芳基、取代的C2至C50的杂芳基是指被一个或多个如下基团所取代：重氢、卤素、硝基、腈基、C1至C30的烷基、C2至C30的烯基、C1至C30的烷氧基、C1至C30的硫醚基、C6至C50的芳基、C2至C50的杂芳基；
L 1、L 2各自独立地包括单键、取代或未取代的C6至C50的亚芳基、取代或未取代的C2至C50的亚杂芳基中的任意一种，这里，取代的C6至C50的亚芳基、取代的C2至C50的亚杂芳基是指被一个或多个如下基团所取代：重氢、卤素、硝基、腈基、C6至C50的芳基、C2至C50的杂芳基。
本公开实施例还提供如上所述的双芳胺化合物作为光取出材料的用途。
本公开实施例还提供光取出材料，包括如上所述的双芳胺化合物。
本公开实施例还提供一种电致发光器件，包括如上所述的双芳胺化合物。
本公开实施例还提供一种显示装置，包括如上所述的电致发光器件。
在阅读并理解了附图和详细描述后，可以明白其他方面。
附图说明
附图用来提供对本公开技术方案的理解，并且构成说明书的一部分，与本公开的实施例一起用于解释本公开的技术方案，并不构成对本公开技术方案的限制。
图1为本公开示例性实施例的电致发光器件的结构示意图。
附图中的标记符号的含义为：
100-阳极；200-空穴注入层；300-空穴传输层；400-电子阻挡层；500-发光层；600-空穴阻挡层；700-电子传输层；800-电子注入层；900-阴极；1000-光取出层。
具体实施方式
本文中的实施方式可以以多个不同形式来实施。所属技术领域的普通技术人员可以很容易地理解一个事实，就是实现方式和内容可以在不脱离本公开的宗旨及其范围的条件下被变换为各种各样的形式。因此，本公开不应该被解释为仅限定在下面的实施方式所记载的内容中。在不冲突的情况下，本公开中的实施例及实施例中的特征可以相互任意组合。
在附图中，有时为了明确起见，可能夸大表示了构成要素的大小、层的厚度或区域。因此，本公开的任意一个实现方式并不一定限定于图中所示尺寸，附图中部件的形状和大小不反映真实比例。此外，附图示意性地示出了理想的例子，本公开的任意一个实现方式不局限于附图所示的形状或数值等。
本公开实施例提供一种双芳胺化合物，其结构通式为：
Figure PCTCN2021140537-appb-000005
其中，A不存在或存在；
i)当A不存在时，萘环与苯环通过键L连接；
Ar 1至Ar 4中的至少两个包括通式II和/或III所示的基团：
Figure PCTCN2021140537-appb-000006
Ar 1至Ar 4中不包括通式II或III所示的基团的包括取代或未取代的C6至C60的芳基、取代或未取代的C5至C60的杂芳基中的任意一种；这里，取代的C6至C60的芳基、取代的C5至C60的杂芳基是指被一个或多个如下基团所取代：重氢、卤素、硝基、腈基、C1至C30的烷基、C2至C30的烯基、C1至C30的烷氧基、C1至C30的硫醚基、C6至C60的芳基和C5至C60的杂芳基；
X 1包括CR 3R 4、O、NR 5或S；X 2包括O或S；
R 1至R 5各自独立地包括氢、重氢、卤素、硝基、腈基、取代或未取代的C1至C30的烷基、取代或未取代的C2至C30的烯基、取代或未取代的C1至C30的烷氧基、取代或未取代的C1至C30的硫醚基、取代或未取代的C6至C50的芳基、取代或未取代的C2至C50的杂芳基中的任意一种，并且当R 1、R 2各自独立地包括取代或未取代的C6至C50的芳基、取代或未取代的C2至C50的杂芳基时，R 1或R 2分别与通式II或III中的苯环通过单键连接或通过共用两个原子的方式稠合连接；这里，取代的C1至C30的烷基、取代的C2至C30的烯基、取代的C1至C30的烷氧基、取代的C1至C30的硫醚基、取代的C6至C50的芳基、取代的C2至C50的杂芳基是指被一个或多个如下基团所取代：重氢、卤素、硝基、腈基、C1至C30的烷基、C2至C30的烯基、C1至C30的烷氧基、C1至C30的硫醚基、C6至C50的芳基、C2至C50的杂芳基；
L 1至L 4各自独立地包括单键、取代或未取代的C6至C50的亚芳基、取代或未取代的C2至C50的亚杂芳基中的任意一种，这里，取代的C6至C50的亚芳基、取代的C2至C50的亚杂芳基是指被一个或多个如下基团所取代：重氢、卤素、硝基、腈基、C6至C50的芳基、C2至C50的杂芳基；
ii)当A存在时，A与键L形成五元环，A为O、S、NR 6、CR 7R 8中的任意一种；
Ar 1至Ar 4中的至少一个包括通式IV或V所示的基团：
Figure PCTCN2021140537-appb-000007
并且Ar 1至Ar 4中的至少一个包括通式VI所示的基团：
Figure PCTCN2021140537-appb-000008
Y 1、Z 1各自独立地包括CR 12R 13、O、NR 14、S中的任意一种，Y 2、Z 2各自独立地包括C或N，Y 3、Z 3均包括N；
Ar 1至Ar 4中不包括通式IV、V、VI所示的基团的包括取代或未取代的C6至C60的芳基、取代或未取代的C5至C60的杂芳基中的任意一种；这里，取代的C6至C60的芳基、取代的C5至C60的杂芳基是指被一个或多个如下基团所取代：重氢、卤素、硝基、腈基、C1至C30的烷基、C2至C30的烯基、C1至C30的烷氧基、C1至C30的硫醚基、C6至C60的芳基和C5至C60的杂芳基；
R 6至R 14各自独立地包括氢、重氢、卤素、硝基、腈基、取代或未取代的C1至C30的烷基、取代或未取代的C2至C30的烯基、取代或未取代的C1至C30的烷氧基、取代或未取代的C1至C30的硫醚基、取代或未取代的C6至C50的芳基、取代或未取代的C2至C50的杂芳基中的任意一种；这里， 取代的C1至C30的烷基、取代的C2至C30的烯基、取代的C1至C30的烷氧基、取代的C1至C30的硫醚基、取代的C6至C50的芳基、取代的C2至C50的杂芳基是指被一个或多个如下基团所取代：重氢、卤素、硝基、腈基、C1至C30的烷基、C2至C30的烯基、C1至C30的烷氧基、C1至C30的硫醚基、C6至C50的芳基、C2至C50的杂芳基；
L 1、L 2各自独立地包括单键、取代或未取代的C6至C50的亚芳基、取代或未取代的C2至C50的亚杂芳基中的任意一种，这里，取代的C6至C50的亚芳基、取代的C2至C50的亚杂芳基是指被一个或多个如下基团所取代：重氢、卤素、硝基、腈基、C6至C50的芳基、C2至C50的杂芳基。
在示例性实施例中，通式II所示的基团可以包括以下基团中的任意一种：
Figure PCTCN2021140537-appb-000009
在示例性实施例中，通式II所示的基团可以包括以下基团中的任意一种：
Figure PCTCN2021140537-appb-000010
在示例性实施例中，通式IV所示的基团可以包括：
Figure PCTCN2021140537-appb-000011
Ar 1至Ar 4中的至少一个包括通式IV-1所示的基团。
在示例性实施例中，通式V所示的基团可以包括：
Figure PCTCN2021140537-appb-000012
Ar 1至Ar 4中的至少一个包括通式V-1所示的基团。
在通式IV-1和通式V-1所示的基团中，五元环中含有三个N原子；多个N原子的存在，使孤对电子间的电子云密度增大，共轭性增加；而且，N原子和相邻苯环上的H形成氢键，增加两个芳香环的平面型，增加片段的极化率，相对其他的位置N取代的杂环，通式IV-1和通式V-1所示的基团的共轭性和平面性更好。
在示例性实施例中，通式IV所示的基团可以包括：
Figure PCTCN2021140537-appb-000013
通式V所示的基团可以包括：
Figure PCTCN2021140537-appb-000014
Ar 1至Ar 4中的至少一个包括通式IV-2或V-2所示的基团。
在示例性实施例中，
通式IV-2所示的基团可以包括：
Figure PCTCN2021140537-appb-000015
在示例性实施例中，通式V-2所示的基团可以包括：
Figure PCTCN2021140537-appb-000016
Figure PCTCN2021140537-appb-000017
在示例性实施例中，所述双芳胺化合物可以包括下述化合物中的任意一种：
Figure PCTCN2021140537-appb-000018
Figure PCTCN2021140537-appb-000019
Figure PCTCN2021140537-appb-000020
Figure PCTCN2021140537-appb-000021
Figure PCTCN2021140537-appb-000022
Figure PCTCN2021140537-appb-000023
Figure PCTCN2021140537-appb-000024
Figure PCTCN2021140537-appb-000025
Figure PCTCN2021140537-appb-000026
Figure PCTCN2021140537-appb-000027
Figure PCTCN2021140537-appb-000028
Figure PCTCN2021140537-appb-000029
Figure PCTCN2021140537-appb-000030
Figure PCTCN2021140537-appb-000031
Figure PCTCN2021140537-appb-000032
Figure PCTCN2021140537-appb-000033
在示例性实施例中，
所述双芳胺化合物在460nm波长处的折射率可以在2.08至2.25范围内；
所述芳胺类化合物在530nm波长处的折射率可以在1.92至2.16范围内；
所述芳胺类化合物在620nm波长处的折射率可以在1.88至2.07范围内。
在示例性实施例中，所述双芳胺化合物在400nm波长处的吸光系数可以在0.84以上，在450nm波长及大于450nm波长处的吸光系数为0。
在示例性实施例中，所述双芳胺化合物的玻璃化转变温度可以在127℃以上。
本公开实施例还提供了如上所述的双芳胺化合物作为光取出材料的用途。
本公开实施例还提供了一种光取出材料，所述光取出材料包括如上所述的双芳胺化合物。
本公开实施例还提供一种电致发光器件，所述电致发光器件包括如上所 述的双芳胺化合物。
在示例性实施例中，所述电致发光器件包括光取出层，所述光取出层的材料可以包括如上所述的双芳胺化合物。
在示例性实施例中，所述电致发光器件可以包括：阳极、空穴注入层(Hole Injection Layer,HIL)、空穴传输层(Hole Transport Layer,HTL)、电子阻挡层(Electron Block Layer,EBL)、发光层(Emitting Layer,EML)、空穴阻挡层(Hole Block Layer,HBL)、电子传输层(Electron Transport Layer,ETL)、电子注入层(Electron Injection Layer,EIL)、阴极和光取出层。
图1为本公开示例性实施例的电致发光器件的结构示意图。如图1所示，所述电致发光器件可以包括：阳极100、空穴注入层200、空穴传输层300、电子阻挡层400、发光层500、空穴阻挡层600、电子传输层700、电子注入层800、阴极900和光取出层1000。所述空穴注入层200设置在所述阳极100一侧的表面上，所述空穴传输层300设置在所述空穴注入层200的远离所述阳极100一侧的表面上，所述电子阻挡层400设置在所述空穴传输层300的远离所述阳极100一侧的表面上，所述发光层500设置在所述电子阻挡层400的远离所述阳极100一侧的表面上，所述空穴阻挡层600设置在所述发光层500的远离所述阳极100一侧的表面上，所述电子传输层700设置在所述空穴阻挡层600的远离所述阳极100一侧的表面上，所述电子注入层800设置在所述电子传输层700的远离所述阳极100一侧的表面上，所述阴极900设置在所述电子注入层800的远离所述阳极100一侧的表面上，所述光取出层1000设置在所述阴极900的远离所述阳极100一侧的表面上。
在示例性实施例中，所述光取出层可以采用本公开实施例提供的光取出材料蒸镀形成。
在示例性实施例中，所述阳极可以为具有高功函数的材料。例如，对于底发射型器件，阳极可以采用透明氧化物材料，如氧化铟锡(ITO)或氧化铟锌(Indium Zinc Oxide,IZO)等。或者，对于顶发射型器件，阳极可以采用金属和透明氧化物的复合结构，如Ag/ITO(氧化铟锡,Indium Tin Oxide)、Ag/IZO(氧化铟锌,Indium Zinc Oxide)、Al/ITO、Al/IZO或者ITO/Ag/ITO等，可保证良好的反射率。
在示例性实施例中，所述空穴注入层的材料可以包括过渡金属氧化物，例如，可以包括钼氧化物、钛氧化物、钒氧化物、铼氧化物、钌氧化物、铬氧化物、锆氧化物、铪氧化物、钽氧化物、银氧化物、钨氧化物、锰氧化物中的任意一种或多种。
在另一示例性实施例中，所述空穴注入层的材料可以包括强吸电子体系的p型掺杂剂和空穴传输材料；
所述p型掺杂剂可以包括2,3,6,7,10,11-六氰基-1,4,5,8,9,12-六氮杂苯并菲、2,3,5,6-四氟-7,7’,8,8’-四氰基对苯醌(F4TCNQ)、1,2,3-三[(氰基)(4-氰基-2,3,5,6-四氟苯基)亚甲基]环丙烷中的任意一种或多种；
所述空穴传输材料可以包括芳胺类空穴传输材料、二甲基芴类空穴传输材料、咔唑类空穴传输材料中的任意一种或多种；例如，所述空穴传输材料可以包括4,4’-双[N-(1-萘基)-N-苯基氨基]联苯(NPB)、N,N’-双(3-甲基苯基)-N,N’-二苯基-[1,1’-联苯]-4,4’-二胺(TPD)、4-苯基-4’-(9-苯基芴-9-基)三苯基胺(BAFLP)、4,4’-双[N-(9,9-二甲基芴-2-基)-N-苯基氨基]联苯(DFLDPBi)、4,4’-二(9-咔唑基)联苯(CBP)和9-苯基-3-[4-(10-苯基-9-蒽基)苯基]-9H-咔唑(PCzPA)中的任意一种或多种。
在示例性实施例中，所述空穴注入层可以通过蒸镀形成。
在示例性实施例中，所述空穴传输层的材料可以包括芳胺类空穴传输材料、二甲基芴类空穴传输材料、咔唑类空穴传输材料中的任意一种或多种；例如，所述空穴传输层的材料可以包括4,4’-双[N-(1-萘基)-N-苯基氨基]联苯(NPB)、N,N’-双(3-甲基苯基)-N,N’-二苯基-[1,1’-联苯]-4,4’-二胺(TPD)、4-苯基-4’-(9-苯基芴-9-基)三苯基胺(BAFLP)、4,4’-双[N-(9,9-二甲基芴-2-基)-N-苯基氨基]联苯(DFLDPBi)、4,4’-二(9-咔唑基)联苯(CBP)和9-苯基-3-[4-(10-苯基-9-蒽基)苯基]-9H-咔唑(PCzPA)中的任意一种或多种。
在示例性实施例中，所述空穴传输层可以通过蒸镀形成。
在示例性实施例中，所述电子阻挡层的材料可以包括芳胺类电子阻挡材料、二甲基芴类电子阻挡材料、咔唑类电子阻挡材料中的任意一种或多种；例如，所述电子阻挡层的材料可以包括4,4’-双[N-(1-萘基)-N-苯基氨基]联苯(NPB)、N,N’-双(3-甲基苯基)-N,N’-二苯基-[1,1’-联苯]-4,4’-二胺(TPD)、4- 苯基-4’-(9-苯基芴-9-基)三苯基胺(BAFLP)、4,4’-双[N-(9,9-二甲基芴-2-基)-N-苯基氨基]联苯(DFLDPBi)、4,4’-二(9-咔唑基)联苯(CBP)和9-苯基-3-[4-(10-苯基-9-蒽基)苯基]-9H-咔唑(PCzPA)中的任意一种或多种。
在示例性实施例中，所述电子阻挡层可以通过蒸镀形成。
在示例性实施例中，所述发光层的材料可以包括一种发光材料，也可以包括两种或两种以上的发光材料。例如，可以包括主体发光材料和掺杂到所述主体发光材料中的客体发光材料。
在示例性实施例中，所述电致发光器件可以为蓝色电致发光器件、绿色电致发光器件或红色电致发光器件，所述蓝色电致发光器件的发光层的材料包括蓝色发光材料，所述绿色电致发光器件的发光层的材料包括绿色发光材料，所述红色电致发光器件的发光层的材料可以包括红色发光材料。
在示例性实施例中，所述蓝色发光材料可以包括芘衍生物类蓝色发光材料、蒽衍生物类蓝色发光材料、芴衍生物类蓝色发光材料、苝衍生物类蓝色发光材料、苯乙烯基胺衍生物类蓝色发光材料和金属配合物类蓝色发光材料中的任意一种或多种。
例如，所述蓝色发光材料可以包括N1,N6-二([1,1’-联苯]-2-基)-N1,N6-二([1,1’-联苯]-4-基)芘-1,6-二胺、9,10-二-(2-萘基)蒽(ADN)、2-甲基-9,10-二-2-萘基蒽(MADN)、2,5,8,11-四叔丁基苝(TBPe)、4,4’-二[4-(二苯氨基)苯乙烯基]联苯(BDAV Bi)、4,4’-二[4-(二对甲苯基氨基)苯乙烯基]联苯(DPAVBi)、二(4,6-二氟苯基吡啶-C2,N)吡啶甲酰合铱(FIrpic)中的任意一种或多种。
在示例性实施例中，所述绿色发光材料可以包括香豆素染料、喹吖啶铜衍生物类绿色发光材料、多环芳香烃类绿色发光材料、二胺蒽衍生物类绿色发光材料、咔唑衍生物类绿色发光材料和金属配合物类绿色发光材料中的任意一种或多种。
例如，所述绿色发光材料可以包括香豆素6(C-6)、香豆素545T(C-525T)、喹吖啶铜(QA)、N,N’-二甲基喹吖啶酮(DMQA)、5,12-二苯基萘并萘(DPT)、N10,N10'-二苯基-N10,N10’-二苯二甲酰-9,9’-二蒽-10,10’-二胺(简称：BA-NPB)、三(8-羟基喹啉)合铝(III)(简称：Alq3)、三(2-苯基吡啶)合铱 (Ir(ppy)3)、乙酰丙酮酸二(2-苯基吡啶)铱(Ir(ppy)2(acac))中的任意一种或多种。
在示例性实施例中，所述红色发光材料可以包括DCM类列红色发光材料和金属配合物类红色发光材料中的任意一种或多种。
例如，所述红色发光材料可以包括4-(二氰基亚甲基)-2-甲基-6-(4-二甲基氨基苯乙烯基)-4H-吡喃(DCM)、4-(二氰基甲撑)-2-叔丁基-6-(1,1,7,7-四甲基久洛尼啶-9-烯基)-4H-吡喃(DCJTB)，二(1-苯基异喹啉)(乙酰丙酮)铱(III)(Ir(piq)2(acac))、八乙基卟啉铂(简称：PtOEP)、二(2-(2’-苯并噻吩基)吡啶-N,C3’)(乙酰丙酮)合铱(简称：Ir(btp)2(acac)中的任意一种或多种。
在示例性实施例中，所述发光层可以通过蒸镀形成。
在示例性实施例中，所述空穴阻挡层的材料可以包括芳族杂环类空穴阻挡材料，例如，可以包括苯并咪唑及其衍生物类空穴阻挡材料、咪唑并吡啶及其衍生物类空穴阻挡材料、苯并咪唑并菲啶衍生物类空穴阻挡材料、嘧啶及其衍生物类空穴阻挡材料、三嗪衍生物类空穴阻挡材料、吡啶及其衍生物类空穴阻挡材料、吡嗪及其衍生物类空穴阻挡材料、喹喔啉及其衍生物类空穴阻挡材料、二唑及其衍生物类空穴阻挡材料、喹啉及其衍生物类空穴阻挡材料、异喹啉衍生物类空穴阻挡材料、菲咯啉衍生物类空穴阻挡材料、二氮磷杂环戊二烯类空穴阻挡材料、氧化膦类空穴阻挡材料、芳族酮类空穴阻挡材料类空穴阻挡材料、内酰胺、硼烷类空穴阻挡材料中的任意一种或多种。
再例如，所述空穴阻挡层的材料可以包括2-(4-联苯基)-5-(4-叔丁基苯基)-1,3,4-噁二唑(PBD)、1,3-双[5-(对叔丁基苯基)-1,3,4-噁二唑-2-基]苯(OXD-7)、3-(4-叔丁基苯基)-4-苯基-5-(4-联苯基)-1,2,4-三唑(TAZ)、3-(4-叔丁基苯基)-4-(4-乙基苯基)-5-(4-联苯基)-1,2,4-三唑(p-EtTAZ)、红菲咯啉(BPhen)、(BCP)、4,4’-双(5-甲基苯并噁唑-2-基)芪(BzOs)中的任意一种或多种。
在示例性实施例中，所述空穴阻挡层可以通过蒸镀形成。
在示例性实施例中，所述电子传输层的材料可以包括芳族杂环类电子传输材料，例如，可以包括苯并咪唑及其衍生物类电子传输材料、咪唑并吡啶及其衍生物类电子传输材料、苯并咪唑并菲啶衍生物类电子传输材料、嘧啶及其衍生物类电子传输材料、三嗪衍生物类电子传输材料、吡啶及其衍生物 类电子传输材料、吡嗪及其衍生物类电子传输材料、喹喔啉及其衍生物类电子传输材料、二唑及其衍生物类电子传输材料、喹啉及其衍生物类电子传输材料、异喹啉衍生物类电子传输材料、菲咯啉衍生物类电子传输材料、二氮磷杂环戊二烯类电子传输材料、氧化膦类电子传输材料、芳族酮类电子传输材料类电子传输材料、内酰胺、硼烷类电子传输材料中的任意一种或多种。
再例如，所述电子传输层的材料可以包括2-(4-联苯基)-5-(4-叔丁基苯基)-1,3,4-噁二唑(PBD)、1,3-双[5-(对叔丁基苯基)-1,3,4-噁二唑-2-基]苯(OXD-7)、3-(4-叔丁基苯基)-4-苯基-5-(4-联苯基)-1,2,4-三唑(TAZ)、3-(4-叔丁基苯基)-4-(4-乙基苯基)-5-(4-联苯基)-1,2,4-三唑(p-EtTAZ)、红菲咯啉(BPhen)、(BCP)、4,4’-双(5-甲基苯并噁唑-2-基)芪(BzOs)中的任意一种或多种。
在示例性实施例中，所述电子传输层可以通过蒸镀形成。
在示例性实施例中，所述电子注入层的材料可以包括碱金属电子注入材料和金属电子注入材料中的任意一种或多种。
例如，所述电子注入层材料可以包括LiF、Yb、Mg、Ca中的任意一种或多种。
在示例性实施例中，所述电子注入层可以通过蒸镀形成。
在示例性实施例中，所述阴极可以采用Al、Ag、Mg等较低功函数的金属形成，或采用含有低功函数金属材料的合金形成。
本公开实施例还提供一种显示装置，所述显示装置包括如上所述的电致发光器件。
在示例性实施例中，所述显示装置可以包括多个所述电致发光器件。例如，所述电致发光器件可以为蓝色电致发光器件、绿色电致发光器件或红色电致发光器件，所述显示装置可以包括蓝色电致发光器件、绿色电致发光器件和红色电致发光器件。
所述显示装置可以为手机、平板电脑、电视机、显示器、笔记本电脑、数码相框、导航仪、车载显示器、智能手表、智能手环等任何具有显示功能的产品或部件。
下面为本公开的一些示例性实施例的双芳胺化合物的合成过程以及性能测试和对比。
本公开的示例性双芳胺化合物的合成方法如下。
合成例1：化合物1的合成
Figure PCTCN2021140537-appb-000034
中间体A1的合成：
反应瓶中加入2-溴-6-碘萘和对溴苯硼酸各0.3mol，然后加入甲苯500ml、乙醇和碳酸钾的水溶液；抽真空充氮气，加入催化剂四(三苯基膦)钯0.003mol，继续抽真空充氮气，加热回流搅拌反应4个小时，然后加入水搅拌，降温至室温后减压过滤，依次使用热水和丙酮冲洗，确保滤液pH值约为7。加入氯仿溶解，浓缩滤液后加入少量甲醇重结晶，减压过滤得到固体，即中间体A1，产率约为88％。
Figure PCTCN2021140537-appb-000035
中间体A2的合成：
反应瓶中加甲苯溶剂400ml，然后加入4-(苯并[D]恶唑-2-基)苯胺0.02mol、 溴苯及叔丁醇钠各0.2mol；充氮气后，加入醋酸钯0.002mol；再进行氮气充气，加入三叔丁基膦的甲苯溶液0.007mol；再重复氮气充气后，回流2小时；反应完成后，将混合物冷却至室温，经硅藻土过滤得滤液，滤液浓缩后加入甲醇，静置重结晶，抽滤并用甲醇淋洗得重结晶固体，得到中间体A2，产率75％；
化合物1的合成：
反应瓶中加入甲苯溶剂100ml，然后依次加入原料中间体A2 0.04mol、中间体A10.02mol及叔丁醇钠0.07mol；充氮气后加入醋酸钯0.1g；再进行氮气充气，加入三叔丁基膦；再重复氮气充气过程，回流2小时；反应完成后，冷却至室温，经硅藻土过滤得滤液，滤液浓缩后加热，加入少量乙醇，静置至室温重结晶，抽滤并用乙醇淋洗得重结晶固体，得到淡黄色固体，即化合物1，产率72％。
质谱m/z：772.28，元素含量(％)：C 54H 36N 4O 2，C，83.92；H，4.69；O，4.14；N，7.25。
1H NMR(500MHz，CDCl 3)：δ7.84(1H)，7.74-7.73(8H)，7.56-7.55(3H)，7.37-7.4(11H)，7.32-7.24(5H)，7.17-7.00(8H)。
合成例2：化合物2的合成
Figure PCTCN2021140537-appb-000036
中间体A1的合成过程与合成例1相同。
中间体A3的合成过程与合成例1中的中间体A2合成过程类似，但将原料4-(苯并[D]恶唑-2-基)苯胺换成2-氨基-苯并恶唑，其他步骤相同，产率83％。
化合物2的合成过程与合成例1中的化合物1合成过程类似，但将中间体A2换成中间体A3，产率76％。
质谱m/z：620.22，元素含量(％)：C 42H 28N 4O 2，C，81.27；H，4.55；O，5.16；N，9.03。
1H NMR(500MHz，CDCl 3)：δ7.84(1H)，7.72(4H)，7.56-7.55(4H)，7.4-7.39(5H)，7.37(4H)，7.32(1H)，7.24(4H)，7.17-7.08(6H)，7.00(2H)。
合成例3：化合物3的合成
Figure PCTCN2021140537-appb-000037
中间体A4的合成过程与合成例2中的中间体A3合成过程类似，但将原料溴苯换成4-溴联苯，其他步骤相同，产率73％。
化合物3的合成过程与合成例2中的化合物2合成过程类似，但将中间体A3换成中间体A4，产率75％。
质谱m/z：772.28，元素含量(％)：C 54H 36N 4O 2，C，83.92；H，4.69；O，4.14；N，7.25。
1H NMR(500MHz，CDCl 3)：δ7.84(1H)，7.75(4H)，7.72(4H)，7.56-7.55(7H)，7.49(4H)，7.41-7.4(3H)，7.39(4H)，7.37(6H)，7.32(1H)，7.17-7.11(2H)。
合成例4：化合物5的合成
Figure PCTCN2021140537-appb-000038
中间体E的合成过程与合成例2中的中间体A3合成过程类似，但将原料溴苯换成2-溴基萘，其他步骤相同，产率88％。
化合物5的合成合成过程与合成例2中的化合物2合成过程类似，但将中间体A3换成中间体E，产率70％。
质谱m/z：720.25，元素含量(％)：C 50H 32N 4O 2，C，83.31；H，4.47；O，4.44；N，7.77。
1H NMR(500MHz，CDCl 3)：δ7.84(1H)，7.78(2H)，7.72(4H)，7.71(2H)，7.56(1H)，7.55(2H)，7.54(2H)，7.45(2H)，7.42(2H)，7.4(3H)，7.39(4H)，7.37(2H)，7.32(1H)，7.17-7.11(4H)。
合成例5：化合物7的合成
Figure PCTCN2021140537-appb-000039
中间体A6的合成过程与合成例1中的中间体A2合成过程类似，但将原料溴苯换成2-溴(9-苯基)咔唑，其他步骤相同，产率71％。
化合物7的过程与合成例1中的化合物1合成过程类似，但将中间体A2换 成中间体A6，产率68％。
质谱m/z：1102.4，元素含量(％)：C 78H 50N 6O 2，C，84.91；H，4.57；O，2.90；N，7.62
1H NMR(500MHz，CDCl 3)：δ8.55(2H)，7.94(2H)，7.84(1H)，7.74(4H)，7.73(4H)，7.62(4H)，7.58(2H)，7.56(1H)，7.55(2H)，7.54(2H)，7.5(4H)，7.4-7.38(5H)，7.37(6H)，7.35(4H)，7.33(2H)，7.32(1H)，7.17-7.11(4H)。
合成例6：化合物12的合成
Figure PCTCN2021140537-appb-000040
中间体A7的合成过程与合成例1中的中间体A2合成过程类似，但将原料4-(苯并[D]恶唑-2-基)苯胺换成4-(2-苯并噻唑基)苯胺，其他步骤相同，产率80％。
化合物12的合成过程与合成例1中的化合物1合成过程类似，但将中间体A2换成中间体A7，产率74％。
质谱m/z：804.24，元素含量(％)：C 54H 36N 4S 2，C，80.57；H，4.51；S，7.96；N，6.96
1H NMR(500MHz，CDCl 3)：δ8.18(2H)，8.02(2H)，7.85-7.84(5H)，7.56-7.55(3H)，7.53(2H)，7.51(2H)，7.4(1H)，7.37(6H)，7.32(1H)，7.24(4H)，7.17(1H)，7.11(1H)，7.08(4H)，7.00(2H)。
合成例7：化合物16的合成
Figure PCTCN2021140537-appb-000041
中间体A8的合成过程与合成例6中的中间体A7合成过程类似，但将原料4-(2-苯并噻唑基)苯胺换成4-(1-苯基苯并咪唑-2-基)苯胺，以及将溴苯换成4-溴联苯，其他步骤相同，产率65％。
化合物16的合成过程与合成例6中的化合物12合成过程类似，但将中间体A7换成中间体A8，产率62％。
质谱m/z：1074.44，元素含量(％)：C 78H 54N 6，C，87.12；H，5.06；N，7.82
1H NMR(500MHz，CDCl 3)：δ8.56(2H)，8.01(4H)，7.84-7.81(3H)，7.75(4H)，7.62(2H)，7.56-7.55(7H)，7.53(2H)，7.49(4H)，7.48(4H)，7.41-7.4(3H)，7.38(4H)，7.37(10H)，7.32(1H)，7.28(2H)，7.17-7.11(2H)。
合成例8：化合物11’的合成
Figure PCTCN2021140537-appb-000042
在反应瓶中加400mL甲苯溶剂，然后加入0.2mol原料B1、0.2mol原料C1及0.1mol叔丁醇钠，充氮气后，加入0.002mol醋酸钯，再进行氮气充气，加入三叔丁基膦的甲苯溶液0.007mol；再重复氮气充气后，回流2小时；反应完成后，将混合物冷却至室温，经硅藻土过滤得滤液，滤液浓缩后加入甲醇，静置重结晶，抽滤并用甲醇淋洗得重结晶固体，得到中间体A9，产率78％。
Figure PCTCN2021140537-appb-000043
在反应瓶中加入400ml甲苯溶剂，然后依次加入0.3mol中间体A9和0.15mol原料C2及0.1mol叔丁醇钠；充氮气后加入0.002mol醋酸钯，再进行氮气充气，加入三叔丁基膦的甲苯溶液0.007mol；再重复氮气充气过程，回流2小时；反应完成后，冷却至室温，经硅藻土过滤得滤液，滤液浓缩后加热，加入少量乙醇，静置至室温重结晶，抽滤并用乙醇淋洗得重结晶固体，得到固体化合物11’，产率75％。
质谱m/z：788.25，元素含量(％)：C 52H 32N 6O 3，C，79.17；H，4.09；O，6.08；N，10.65。
1H NMR(500MHz，CDCl 3)：δ8.03-8.04(3H),7.92(2H),7.8(1H),7.73-7.74(8H),7.54(1H),7.49(1H),7.42(2H),7.36-7.38(10H),7.11-7.11(3H),6.91(1H)。
合成例9：化合物12’的合成
Figure PCTCN2021140537-appb-000044
反应瓶中加400ml甲苯溶剂，然后加入0.2mol原料B1、0.2mol原料C3及0.1mol叔丁醇钠，充氮气后，加入0.002mol醋酸钯，再进行氮气充气，加入三叔丁基膦的甲苯溶液0.007mol；再重复氮气充气后，回流2小时；反应完成后，将混合物冷却至室温，经硅藻土过滤得滤液，滤液浓缩后加入甲醇，静置重结晶，抽滤并用甲醇淋洗得重结晶固体，得到中间体A10，产率76％。
Figure PCTCN2021140537-appb-000045
在反应瓶中加入400ml甲苯溶剂，然后依次加入0.3mol中间体A10和0.15mol原料C2及0.1mol叔丁醇钠；充氮气后加入0.002mol醋酸钯，再进行氮气充气，加入三叔丁基膦的甲苯溶液0.007mol；再重复氮气充气过程，回流2小时；反应完成后，冷却至室温，经硅藻土过滤得滤液，滤液浓缩后加热，加入少量乙醇，静置至室温重结晶，抽滤并用乙醇淋洗得重结晶固体，得到固体化合物12’，产率70％。
质谱m/z：788.2536：C 52H 32N 6O 3，C，79.17；H，4.09；N，10.65；O，6.08。
1H NMR(500MHz，CDCl 3)：δ8.03-8.04(3H),7.8(1H),7.73-7.74(8H),7.54-7.55(3H),7.49(1H),7.42(2H),7.38-7.37(8H),7.11(1H),6.91(1H),6.73(2H),6.63(2H)。
合成例10：化合物13’的合成
Figure PCTCN2021140537-appb-000046
在反应瓶中加400ml甲苯溶剂，然后加入0.2mol原料B1、0.2mol原料C4及0.1mol叔丁醇钠，充氮气后，加入0.002mol醋酸钯，再进行氮气充气，加入三叔丁基膦的甲苯溶液0.007mol；再重复氮气充气后，回流2小时；反应完成后，将混合物冷却至室温，经硅藻土过滤得滤液，滤液浓缩后加入甲醇，静置重结晶，抽滤并用甲醇淋洗得重结晶固体，得到中间体A11，产率78％。
Figure PCTCN2021140537-appb-000047
在反应瓶中加入400ml甲苯溶剂，然后依次加入0.3mol中间体A11、0.15mol原料C2及0.1mol叔丁醇钠；充氮气后加入0.002mol醋酸钯，再进行氮 气充气，加入三叔丁基膦的甲苯溶液0.007mol；再重复氮气充气过程，回流2小时；反应完成后，冷却至室温，经硅藻土过滤得滤液，滤液浓缩后加热，加入少量乙醇，静置至室温重结晶，抽滤并用乙醇淋洗得重结晶固体，得到固体化合物13’，产率76％。
质谱m/z：788.2536：C 52H 32N 6O 3，C，79.17；H，4.09；N，10.65；O，6.08；
1H NMR(500MHz，CDCl 3)：δ8.46(4H),8.03(1H),7.8(1),7.73-7.74(8H),7.5(1H),7.49(1H),7.42(2H),7.38-7.37(8H),7.11(1H),6.99(4H),6.91(1H)。
合成例11：化合物32’的合成
Figure PCTCN2021140537-appb-000048
在反应瓶中加400ml甲苯溶剂，然后加入0.2mol原料B2、0.2mol原料C1及0.1mol叔丁醇钠，充氮气后，加入醋酸钯0.002mol，再进行氮气充气，加入三叔丁基膦的甲苯溶液0.007mol；再重复氮气充气后，回流2小时；反应完成后，将混合物冷却至室温，经硅藻土过滤得滤液，滤液浓缩后加入甲醇，静置重结晶，抽滤并用甲醇淋洗得重结晶固体，得到中间体A12，产率71％。
Figure PCTCN2021140537-appb-000049
化合物32’的合成过程与合成例8中化合物11’的合成过程类似，但将原料换成中间体A12和原料C5，其他步骤相同，产率75％。
质谱m/z：836.19，元素含量(％)：C 52H 32N 6S 3，C，74.62；H，3.85；N，10.04；S，11.49。
1H NMR(500MHz，CDCl 3)：δ8.18(2H),8.01-8.04(5H),7.92(2H),7.85-7.86(5H),7.73-7.74(8H),7.78(1H),7.64(1H),7.54(1H),7.51-7.53(3H),7.42-7.43(2H),7.36-7.37(6H),7.24(4),7.11-7.15(3H)。
合成例12：化合物41’的合成
Figure PCTCN2021140537-appb-000050
在反应瓶中加400ml甲苯溶剂，然后加入0.2mol原料B2、0.2mol原料C1及0.1mol叔丁醇钠，充氮气后，加入醋酸钯0.002mol，再进行氮气充气，加入三叔丁基膦的甲苯溶液0.007mol；再重复氮气充气后，回流2小时；反应完成后，将混合物冷却至室温，经硅藻土过滤得滤液，滤液浓缩后加入甲醇，静置重结晶，抽滤并用甲醇淋洗得重结晶固体，得到中间体A12，产率 77％。
Figure PCTCN2021140537-appb-000051
化合物41’的合成过程与合成例8中化合物11’的合成过程类似，但将原料换成中间体A12和原料C2，其他步骤相同，产率75％。
质谱m/z：820.207)：C 52H 32N 6OS 2，C，76.08；H，3.93；N，10.24；O，1.95；S,7.81。
1H NMR(500MHz，CDCl 3)：δ8.18(2H)，8.02-8.04(5H),7.92(2H),7.85(4H),7.8(1H),7.49-7.54(6H),7.42(2H),7.36-7.37(6H),7.11-7.15(3H),6.91(1H)。
合成例13：化合物56’的合成
Figure PCTCN2021140537-appb-000052
在反应瓶中加400ml甲苯溶剂，然后加入0.2mol原料B3、0.2mol原料C1及0.1mol叔丁醇钠，充氮气后，加入醋酸钯0.002mol，再进行氮气充气，加入三叔丁基膦的甲苯溶液0.007mol；再重复氮气充气后，回流2小时；反应完成后，将混合物冷却至室温，经硅藻土过滤得滤液，滤液浓缩后加入甲醇， 静置重结晶，抽滤并用甲醇淋洗得重结晶固体，得到中间体A13，产率70％。
Figure PCTCN2021140537-appb-000053
化合物56’的合成过程与合成例8中化合物11’的合成过程类似，但将原料换成中间体A13和原料C5，其他步骤相同，产率75％。
质谱m/z：804.2532，元素含量(％)：C 50H 32N 10S，C，74.61；H，4.01；N，17.40；S,3.98。
1H NMR(500MHz，CDCl 3)：δ8.03(6H),7.92(3H),7.86(1H),7.78(1H),7.64(1H),7.54-7.57(9H).7.42-7.43(2H),7.36(2H),7.11-7.18(7)。
双芳胺化合物的折射率
折射率采用椭偏仪测试；仪器扫描范围为245nm至1000nm；采用硅片蒸镀形成化合物的薄膜，薄膜厚度为50nm，然后测试折射率。
其中，作为对比的化合物CP1、CP2为以下化合物：
Figure PCTCN2021140537-appb-000054
测试结果如表1所示。
表1
Figure PCTCN2021140537-appb-000055
Figure PCTCN2021140537-appb-000056
可以看出，与对比例1、2的化合物CP1、CP2相比，本公开实施例的化合物在不同波长处的折射率更高。折射率是光取出材料的重要物理参数，折射率大小直接决定改了器件的光耦合效率。因此本公开实施例的化合物适于作为光取出材料，可以明显提高器件出光效率，获得更高的外量子效率，减少光在器件内部的损耗，进而提高器件的效率。
双芳胺化合物的吸光系数
采用玻璃基板蒸镀形成含有双芳胺化合物的薄膜，薄膜厚度为50nm，然后采用紫外可见吸收光谱仪测试吸光系数。
测试结果如表2。
表2
Figure PCTCN2021140537-appb-000057
Figure PCTCN2021140537-appb-000058
为保护OLED器件不受外界环境中紫外光的破坏，CPL材料需在400nm左右有较强的吸收能力，吸收外界紫外光，防止器件老化。同时不能对OLED器件本身发出的光有吸收，因此要求在450nm及之后的吸收需要几乎为0。
可以看出，相较于对比化合物CP1、CP2，本公开实施例的化合物在400nm波长处的吸光系数明显更高，因此可以更好地吸收紫外光；而且，本公开实施例的化合物在450nm波长处的吸收为零，在大于450nm波长处的吸收也均为零(表中未示)，表明不会吸收器件本身发出的光。
双芳胺化合物的玻璃化转变温度
玻璃化转变温度的测量仪器为DSC差示扫描量热仪；测试气氛为氮气，升温速率为为10℃/min，温度范围为50℃至300℃；所测得的玻璃转化温度 (Tg)如表3所示。
表3
化合物 Tg℃ 化合物 Tg℃
对比例1(CP1) 130 化合物1’ 128
对比例2(CP2) 125 化合物2’ 127
化合物1 133 化合物3’ 131
化合物2 131 化合物4’ 129
化合物3 134 化合物5’ 130
化合物4 133 化合物6’ 130
化合物5 135 化合物7’ 138
化合物6 138 化合物8’ 136
化合物8 137 化合物23’ 134
化合物11 133 化合物24’ 137
化合物12 134 化合物31’ 133
化合物13 135 化合物32’ 136
化合物14 136 化合物39’ 138
化合物15 138 化合物40’ 135
化合物16 140 化合物46’ 130
化合物17 139 化合物47’ 132
化合物20 132 化合物48’ 138
化合物22 133 化合物49’ 134
化合物24 135 化合物50’ 142
化合物25 137 化合物51’ 138
化合物27 139 化合物57’ 131
化合物28 141 化合物58’ 134
化合物31 140 化合物59’ 132
化合物35 145 化合物60’ 134
化合物37 134 化合物65’ 139
化合物38 139 化合物66’ 140
    化合物67’ 135
    化合物68’ 132
玻璃换转变温度(Tg)的高低决定了材料在蒸镀中的热稳定性，Tg越高，材料热稳定性越好。一般Tg在110℃以上就可以满足蒸镀要求。可以看出，本公开实施例的化合物的玻璃化转变温度Tg均较高，均在120℃以上。因此本公开实施例的化合物适于作为光取出材料，在蒸镀工艺中具有很好的稳定性，可以解决蒸镀工艺中因为加热而材料不稳定造成的分解杂质变多的问题，有利于提高器件中材料的稳定性和器件的寿命。
下面对本公开的一些示例性实施例的电致发光器件的性能进行测试和对比。
OLED器件性能测试
其中采用的部分原料的化学结构如表4所示。
表4
Figure PCTCN2021140537-appb-000059
Figure PCTCN2021140537-appb-000060
Figure PCTCN2021140537-appb-000061
OLED器件的制备过程包括：将事先制备好的ITO基板进行清洗并烘干；在阳极上依次蒸镀HIL材料、HTL材料、EBL材料；之后蒸镀发光层材料；在发光层上蒸镀HBL材料、ETL材料、EIL材料；之后再蒸镀阴极；在阴极之上，蒸镀本公开实施例的化合物形成CPL层。器件采用玻璃UV封装。也可以采用薄膜封装(Thin-Film Encapsulation,TFE)，但CPL上需要蒸镀LIF或者折射率n≤1.6的有机材料。
测试例1
在该测试例中，CPL层的材料在本公开实施例提供的化合物1至化合物38中选择。
第一蓝色OLED器件的结构以及厚度
ITO/m-MTDATA:F4TCNQ 3％10nm/m-MTDATA 100nm/CBP 10nm/BH1:BD1 5％20nm/TPBI 5nm/BCP:Liq 1:1 30nm/Yb 1nm/Mg：Ag 13nm/CPL 60nm
第一绿色OLED器件的结构以及厚度
ITO/m-MTDATA:F4TCNQ 3％10nm/m-MTDATA 100nm/CBP 45nm/GH:GD 10％40nm/TPBI 5nm/BCP:Liq 1:1 30nm/Yb 1nm/Mg：Ag 13nm/CPL 60nm
第一红色OLED器件的结构以及厚度
ITO/m-MTDATA:F4TCNQ 3％10nm/m-MTDATA 100nm/CBP 75nm/RH:RD 3％45nm/TPBI 5nm/BCP:Liq 1:1 30nm/Yb 1nm/Mg：Ag 13nm/CPL 60nm
第一蓝色OLED器件的性能如表5所示。
表5
Figure PCTCN2021140537-appb-000062
Figure PCTCN2021140537-appb-000063
可以看出，与对比例采用CP1和CP2作为CPL材料制备的器件相比，采用本公开实施例的化合物作为CPL材料制备的蓝色OLED器件的取光效率(EQE)更高，稳定性更好，效率和寿命都得到了提升。
红色OLED器件和绿色OLED器件的取光效率趋势与蓝色OLED器件类似。因此，采用本公开实施例的高折射率化合物作为OLED器件的CPL材料，可以提高OLED器件的取光效率。又由于CPL材料的热稳定性的提高，使得器件的寿命相对提高。
测试例2
在该测试例中，CPL层的材料在本公开实施例提供的化合物1’至化合物69’中选择。
第二蓝色OLED器件的结构以及厚度
ITO/m-MTDATA:F4TCNQ 3％10nm/m-MTDATA 110nm/CBP 5nm/BH1:BD1 5％20nm/TPBI 5nm/BCP:Liq 1:1 30nm/Yb 1nm/Mg：Ag 13nm/CPL 65nm
第二绿色OLED器件的结构以及厚度
ITO/m-MTDATA:F4TCNQ 3％10nm/m-MTDATA 110nm/CBP 45nm/GH:GD 10％40nm/TPBI 5nm/BCP:Liq 1:1 30nm/Yb 1nm/Mg：Ag 13nm/CPL 65nm
第二红色OLED器件的结构以及厚度
ITO/m-MTDATA:F4TCNQ 3％10nm/m-MTDATA 100nm/CBP 75nm/RH:RD 3％45nm/TPBI 5nm/BCP:Liq 1:1 30nm/Yb 1nm/Mg：Ag 13nm/CPL 65nm
第二蓝色OLED器件的性能如表6所示。
表6
Figure PCTCN2021140537-appb-000064
第二绿色OLED器件的性能如表7所示。
表7
Figure PCTCN2021140537-appb-000065
第二红色OLED器件的性能如表8所示。
表8
Figure PCTCN2021140537-appb-000066
可以看出，与对比例采用CP1和CP2作为CPL材料制备的器件相比，采用本公开实施例的双芳胺化合物作为CPL材料制备的器件的光取出效率(EQE)更高、稳定性得到一定提升、效率和寿命都得到了改善。
虽然本公开所揭露的实施方式如上，但所述的内容仅为便于理解本公开而采用的实施方式，并非用以限定本公开。任何所属领域内的技术人员，在不脱离本公开所揭露的精神和范围的前提下，可以在实施的形式及细节上进行任何的修改与变化，但本申请的专利保护范围，仍须以所附的权利要求书所界定的范围为准。

Claims (20)

  1. 一种双芳胺化合物，其结构通式为：
    Figure PCTCN2021140537-appb-100001
    其中，A不存在或存在；
    i)当A不存在时，萘环与苯环通过键L连接；
    Ar 1至Ar 4中的至少两个包括通式II和/或III所示的基团：
    Figure PCTCN2021140537-appb-100002
    Ar 1至Ar 4中不包括通式II或III所示的基团的包括取代或未取代的C6至C60的芳基、取代或未取代的C5至C60的杂芳基中的任意一种；这里，取代的C6至C60的芳基、取代的C5至C60的杂芳基是指被一个或多个如下基团所取代：重氢、卤素、硝基、腈基、C1至C30的烷基、C2至C30的烯基、C1至C30的烷氧基、C1至C30的硫醚基、C6至C60的芳基和C5至C60的杂芳基；
    X 1包括CR 3R 4、O、NR 5或S；X 2包括O或S；
    R 1至R 5各自独立地包括氢、重氢、卤素、硝基、腈基、取代或未取代的C1至C30的烷基、取代或未取代的C2至C30的烯基、取代或未取代的C1至C30的烷氧基、取代或未取代的C1至C30的硫醚基、取代或未取代的C6至C50的芳基、取代或未取代的C2至C50的杂芳基中的任意一种，并且当R 1、R 2各自独立地包括取代或未取代的C6至C50的芳基、取代或未取代 的C2至C50的杂芳基时，R 1或R 2分别与通式II或III中的苯环通过单键连接或通过共用两个原子的方式稠合连接；这里，取代的C1至C30的烷基、取代的C2至C30的烯基、取代的C1至C30的烷氧基、取代的C1至C30的硫醚基、取代的C6至C50的芳基、取代的C2至C50的杂芳基是指被一个或多个如下基团所取代：重氢、卤素、硝基、腈基、C1至C30的烷基、C2至C30的烯基、C1至C30的烷氧基、C1至C30的硫醚基、C6至C50的芳基、C2至C50的杂芳基；
    L 1至L 4各自独立地包括单键、取代或未取代的C6至C50的亚芳基、取代或未取代的C2至C50的亚杂芳基中的任意一种，这里，取代的C6至C50的亚芳基、取代的C2至C50的亚杂芳基是指被一个或多个如下基团所取代：重氢、卤素、硝基、腈基、C6至C50的芳基、C2至C50的杂芳基；
    ii)当A存在时，A与键L形成五元环，A包括O、S、NR 6、CR 7R 8中的任意一种；
    Ar 1至Ar 4中的至少一个包括通式IV或V所示的基团：
    Figure PCTCN2021140537-appb-100003
    并且Ar 1至Ar 4中的至少一个包括通式VI所示的基团：
    Figure PCTCN2021140537-appb-100004
    Y 1、Z 1各自独立地包括CR 12R 13、O、NR 14、S中的任意一种，Y 2、Z 2 各自独立地包括C或N，Y 3、Z 3均包括N；
    Ar 1至Ar 4中不包括通式IV、V、VI所示的基团的包括取代或未取代的C6至C60的芳基、取代或未取代的C5至C60的杂芳基中的任意一种；这里，取代的C6至C60的芳基、取代的C5至C60的杂芳基是指被一个或多个如下基团所取代：重氢、卤素、硝基、腈基、C1至C30的烷基、C2至C30的烯基、C1至C30的烷氧基、C1至C30的硫醚基、C6至C60的芳基和C5至C60的杂芳基；
    R 6至R 14各自独立地包括氢、重氢、卤素、硝基、腈基、取代或未取代的C1至C30的烷基、取代或未取代的C2至C30的烯基、取代或未取代的C1至C30的烷氧基、取代或未取代的C1至C30的硫醚基、取代或未取代的C6至C50的芳基、取代或未取代的C2至C50的杂芳基中的任意一种；这里，取代的C1至C30的烷基、取代的C2至C30的烯基、取代的C1至C30的烷氧基、取代的C1至C30的硫醚基、取代的C6至C50的芳基、取代的C2至C50的杂芳基是指被一个或多个如下基团所取代：重氢、卤素、硝基、腈基、C1至C30的烷基、C2至C30的烯基、C1至C30的烷氧基、C1至C30的硫醚基、C6至C50的芳基、C2至C50的杂芳基；
    L 1、L 2各自独立地包括单键、取代或未取代的C6至C50的亚芳基、取代或未取代的C2至C50的亚杂芳基中的任意一种，这里，取代的C6至C50的亚芳基、取代的C2至C50的亚杂芳基是指被一个或多个如下基团所取代：重氢、卤素、硝基、腈基、C6至C50的芳基、C2至C50的杂芳基。
  2. 根据权利要求1所述的双芳胺化合物，其中，通式II所示的基团包括以下基团中的任意一种：
    Figure PCTCN2021140537-appb-100005
    Figure PCTCN2021140537-appb-100006
  3. 根据权利要求2所述的双芳胺化合物，其中，通式II所示的基团包括以下基团中的任意一种：
    Figure PCTCN2021140537-appb-100007
  4. 根据权利要求1所述的双芳胺化合物，其中，通式IV所示的基团包括：
    Figure PCTCN2021140537-appb-100008
    Ar 1至Ar 4中的至少一个包括通式IV-1所示的基团。
  5. 根据权利要求1所述的双芳胺化合物，其中，通式V所示的基团包括：
    Figure PCTCN2021140537-appb-100009
    Ar 1至Ar 4中的至少一个包括通式V-1所示的基团。
  6. 根据权利要求1所述的双芳胺化合物，其中，通式IV所示的基团包括：
    Figure PCTCN2021140537-appb-100010
    通式V所示的基团包括：
    Figure PCTCN2021140537-appb-100011
    Ar 1至Ar 4中的至少一个包括通式IV-2或V-2所示的基团。
  7. 根据权利要求6所述的双芳胺化合物，其中，
    通式IV-2所示的基团包括：
    Figure PCTCN2021140537-appb-100012
    或者，
    通式V-2所示的基团包括：
    Figure PCTCN2021140537-appb-100013
    Figure PCTCN2021140537-appb-100014
  8. 根据权利要求1所述的双芳胺化合物，其中，所述双芳胺化合物包括下述化合物中的任意一种：
    Figure PCTCN2021140537-appb-100015
    Figure PCTCN2021140537-appb-100016
    Figure PCTCN2021140537-appb-100017
    Figure PCTCN2021140537-appb-100018
    Figure PCTCN2021140537-appb-100019
    Figure PCTCN2021140537-appb-100020
    Figure PCTCN2021140537-appb-100021
    Figure PCTCN2021140537-appb-100022
    Figure PCTCN2021140537-appb-100023
    Figure PCTCN2021140537-appb-100024
    Figure PCTCN2021140537-appb-100025
    Figure PCTCN2021140537-appb-100026
    Figure PCTCN2021140537-appb-100027
    Figure PCTCN2021140537-appb-100028
    Figure PCTCN2021140537-appb-100029
    Figure PCTCN2021140537-appb-100030
  9. 根据权利要求1至8中任一项所述的双芳胺化合物，其中，
    所述双芳胺化合物在460nm波长处的折射率在2.08至2.25范围内；
    所述芳胺类化合物在530nm波长处的折射率在1.92至2.16范围内；
    所述芳胺类化合物在620nm波长处的折射率在1.88至2.07范围内。
  10. 根据权利要求1至8中任一项所述的双芳胺化合物，其中，所述双芳胺化合物在400nm波长处的吸光系数在0.84以上，在450nm波长及大于450nm波长处的吸光系数为零。
  11. 根据权利要求1至8中任一项所述的双芳胺化合物，其中，所述双芳胺化合物的玻璃化转变温度在127℃以上。
  12. 根据权利要求1至11中任一项所述的双芳胺化合物作为光取出材料的用途。
  13. 一种光取出材料，包括根据权利要求1至11中任一项所述的双芳胺化合物。
  14. 一种电致发光器件，包括根据权利要求1至11中任一项所述的双芳胺化合物。
  15. 根据权利要求14所述的电致发光器件，包括：阳极、空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层、阴极和光取出层。
  16. 根据权利要求15所述的电致发光器件，其中，
    a)所述空穴注入层的材料包括过渡金属氧化物；
    所述过渡金属氧化物包括钼氧化物、钛氧化物、钒氧化物、铼氧化物、钌氧化物、铬氧化物、锆氧化物、铪氧化物、钽氧化物、银氧化物、钨氧化物、锰氧化物中的任意一种或多种；或者
    b)所述空穴注入层的材料包括p型掺杂剂和空穴传输材料；
    所述p型掺杂剂包括2,3,6,7,10 11-六氰基-1,4,5,8,9,12-六氮杂苯并菲、2,3,5,6-四氟-7,7’,8,8’-四氰基对苯醌、1,2,3-三[(氰基)(4-氰基-2,3,5,6-四氟苯基)亚甲基]环丙烷中的任意一种或多种；
    所述空穴传输材料包括芳胺类空穴传输材料、二甲基芴类空穴传输材料、咔唑类空穴传输材料中的任意一种或多种。
  17. 根据权利要求15所述的电致发光器件，其中，所述空穴传输层的材料包括芳胺类空穴传输材料、二甲基芴类空穴传输材料、咔唑类空穴传输材料中的任意一种或多种；
    所述电子阻挡层的材料包括芳胺类电子阻挡材料、二甲基芴类电子阻挡材料、咔唑类电子阻挡材料中的任意一种或多种。
  18. 根据权利要求15所述的电致发光器件，其中，所述电致发光器件为蓝色电致发光器件、绿色电致发光器件或红色电致发光器件，所述蓝色电致发光器件的发光层的材料包括蓝色发光材料，所述绿色电致发光器件的发光层的材料包括绿色发光材料，所述红色电致发光器件的发光层的材料包括红色发光材料；
    所述蓝色发光材料包括芘衍生物类蓝色发光材料、蒽衍生物类蓝色发光材料、芴衍生物类蓝色发光材料、苝衍生物类蓝色发光材料、苯乙烯基胺衍生物类蓝色发光材料和金属配合物类蓝色发光材料中的任意一种或多种；
    所述绿色发光材料包括香豆素染料、喹吖啶铜衍生物类绿色发光材料、多环芳香烃类绿色发光材料、二胺蒽衍生物类绿色发光材料、咔唑衍生物类绿色发光材料和金属配合物类绿色发光材料中的任意一种或多种；
    所述红色发光材料包括DCM类列红色发光材料和金属配合物类红色发光材料中的任意一种或多种。
  19. 根据权利要求15所述的电致发光器件，其中，所述空穴阻挡层的材料包括苯并咪唑及其衍生物类空穴阻挡材料、咪唑并吡啶及其衍生物类空穴阻挡材料、苯并咪唑并菲啶衍生物类空穴阻挡材料、嘧啶及其衍生物类空穴阻挡材料、三嗪衍生物类空穴阻挡材料、吡啶及其衍生物类空穴阻挡材料、吡嗪及其衍生物类空穴阻挡材料、喹喔啉及其衍生物类空穴阻挡材料、二唑及其衍生物类空穴阻挡材料、喹啉及其衍生物类空穴阻挡材料、异喹啉衍生物类空穴阻挡材料、菲咯啉衍生物类空穴阻挡材料、二氮磷杂环戊二烯类空穴阻挡材料、氧化膦类空穴阻挡材料、芳族酮类空穴阻挡材料类空穴阻挡材料、内酰胺、硼烷类空穴阻挡材料中的任意一种或多种；
    所述电子传输层的材料包括苯并咪唑及其衍生物类电子传输材料、咪唑并吡啶及其衍生物类电子传输材料、苯并咪唑并菲啶衍生物类电子传输材料、嘧啶及其衍生物类电子传输材料、三嗪衍生物类电子传输材料、吡啶及其衍生物类电子传输材料、吡嗪及其衍生物类电子传输材料、喹喔啉及其衍生物类电子传输材料、二唑及其衍生物类电子传输材料、喹啉及其衍生物类电子 传输材料、异喹啉衍生物类电子传输材料、菲咯啉衍生物类电子传输材料、二氮磷杂环戊二烯类电子传输材料、氧化膦类电子传输材料、芳族酮类电子传输材料类电子传输材料、内酰胺、硼烷类电子传输材料中的任意一种或多种；
    所述电子注入层的材料包括碱金属电子注入材料和金属电子注入材料中的任意一种或多种。
  20. 一种显示装置，包括根据权利要求14至19中任一项所述的电致发光器件。
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