CN106317041A - 发光材料及其制备方法与使用该发光材料的有机发光二极管 - Google Patents
发光材料及其制备方法与使用该发光材料的有机发光二极管 Download PDFInfo
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- CN106317041A CN106317041A CN201610579501.9A CN201610579501A CN106317041A CN 106317041 A CN106317041 A CN 106317041A CN 201610579501 A CN201610579501 A CN 201610579501A CN 106317041 A CN106317041 A CN 106317041A
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- -1 aromatic amine compound Chemical class 0.000 claims description 18
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- 125000003368 amide group Chemical group 0.000 claims description 6
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- 125000006280 2-bromobenzyl group Chemical group [H]C1=C([H])C(Br)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 229910021529 ammonia Inorganic materials 0.000 claims 1
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- HNGQQUDFJDROPY-UHFFFAOYSA-N 3-bromobenzenethiol Chemical compound SC1=CC=CC(Br)=C1 HNGQQUDFJDROPY-UHFFFAOYSA-N 0.000 abstract 1
- HGXWRDPQFZKOLZ-UHFFFAOYSA-N 4-bromo-2-fluorobenzonitrile Chemical compound FC1=CC(Br)=CC=C1C#N HGXWRDPQFZKOLZ-UHFFFAOYSA-N 0.000 abstract 1
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 229910052763 palladium Inorganic materials 0.000 description 7
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- PAMBVPQLDDXPCQ-UHFFFAOYSA-N boric acid;n,n-diphenylaniline Chemical compound OB(O)O.C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 PAMBVPQLDDXPCQ-UHFFFAOYSA-N 0.000 description 4
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- 150000004982 aromatic amines Chemical group 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
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- 238000002156 mixing Methods 0.000 description 3
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- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
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- 238000010438 heat treatment Methods 0.000 description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 description 1
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
- IWCBFNUUALXQBB-UHFFFAOYSA-N B(O)(O)O.B(F)(F)F Chemical compound B(O)(O)O.B(F)(F)F IWCBFNUUALXQBB-UHFFFAOYSA-N 0.000 description 1
- 208000036626 Mental retardation Diseases 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 230000004308 accommodation Effects 0.000 description 1
- 229940008309 acetone / ethanol Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- GSRACRUJMDHCAF-UHFFFAOYSA-N boric acid;9h-carbazole Chemical compound OB(O)O.C1=CC=C2C3=CC=CC=C3NC2=C1 GSRACRUJMDHCAF-UHFFFAOYSA-N 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 1
- 238000010849 ion bombardment Methods 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 238000010129 solution processing Methods 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
- C07D335/14—Thioxanthenes 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 in position 9
- C07D335/16—Oxygen atoms, e.g. thioxanthones
-
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
本发明提供一种发光材料及其制备方法与使用该发光材料的有机发光二极管。本发明的发光材料,结构单一,分子量确定,具有较好的溶解性及成膜性,且薄膜形态稳定;具有很高的分解温度和比较低的升华温度,容易升华成高纯度的发光材料,可应用于小分子有机发光二极管。本发明的发光材料的制备方法,以间溴苯硫酚与2‑氟‑4‑溴苄腈为起始原料,通过一系列的简单反应得到发光材料的中间体,最后通过乌尔曼反应或铃木反应得到发光材料,步骤简单,产率高。本发明的有机发光二极管,发光层含有上述发光材料,具有较高的发光效率与稳定性。
Description
技术领域
本发明涉及显示技术领域,尤其涉及一种发光材料及其制备方法与使用该发光材料的有机发光二极管。
背景技术
有机发光二极管(OLED,Organic Light-Emitting Diode)显示器,也称为有机电致发光显示器,是一种新兴的平板显示装置,由于其具有制备工艺简单、成本低、功耗低、发光亮度高、工作温度适应范围广、体积轻薄、响应速度快,而且易于实现彩色显示和大屏幕显示、易于实现和集成电路驱动器相匹配、易于实现柔性显示等优点,因而具有广阔的应用前景。
OLED显示器利用有机发光二极管进行发光,因此改善有机发光二极管的效率和寿命显得极为重要。至今,有机发光二极管已经取得了长足的进展,通过荧光磷光杂化,可以获得器件结构简单且效率很高的白光器件。而这种荧光磷光杂化器件的效率很大程度上依赖于荧光的效率,因此发展高效的荧光材料依然具有举足轻重的意义。
相比于聚合物而言,发光小分子由于制备步骤简便,结构稳定,能够纯化,因而可以获得更高的器件效率,从而可得到商业化应用。利用小分子进行蒸镀或者溶液加工,制备多层器件的方法已经受到了极大关注,并且取得了巨大的进展。但是基于传统的有机荧光材料由于通常只能利用25%的单线态激子,因此器件的效率受到极大的限制。而近期,由日本人Adachi课题组利用热活化延迟荧光机理,使全有机材料的激子利用率也可以达到100%,使得有机荧光的器件效率实现了飞跃。然而由于这类材料种类稀少,因而拓展这类材料的种类对未来的应用选择具有很重要的意义。至今为止,结构简单、且兼具良好性能、满足商业化需求的有机小分子发光材料依旧十分有限,开发成本低廉且效率优异的发光材料依然具有举足轻重的意义。
发明内容
本发明的目的在于提供一种发光材料,结构单一,分子量确定,具有较好的溶解性及成膜性,可应用于小分子有机发光二极管。
本发明的目的还在于提供一种发光材料的制备方法,步骤简单,产率高。
本发明的目的还在于提供一种有机发光二极管,发光层含有上述发光材料,具有较高的发光效率与稳定性。
为实现上述目的,本发明首先提供一种发光材料,结构通式为其中,Ar1、Ar2分别选自式(1)、式(2)、式(3)、式(4)、式(5)、式(6)、式(7)所示的芳香氨基团;
Ar1与Ar2相同。
所述发光材料包括以下化合物中的一种或多种:
本发明还提供一种发光材料的制备方法,包括如下步骤:
步骤1、制备中间体
步骤2、中间体与芳香胺化合物通过乌尔曼反应或铃木反应得到发光材料,所述发光材料的结构通式为其中,Ar1、Ar2分别选自式(1)、式(2)、式(3)、式(4)、式(5)、式(6)、式(7)所示的芳香氨基团;
Ar1与Ar2相同。
所述发光材料包括以下化合物中的一种或多种:
所述步骤1包括:
步骤11、间溴苯硫酚与2-氟-4-溴苄腈反应得到
步骤12、先在碱性条件下水解,再酸化,得到
步骤13、发生脱水缩合反应,得到和中间体
本发明提供一种有机发光二极管,包括基板、在基板上从下到上依次层叠设置的阳极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层、及阴极;
所述发光层包括发光材料,所述发光材料的结构通式为
其中,Ar1、Ar2分别选自式(1)、式(2)、式(3)、式(4)、式(5)、式(6)、式(7)所示的芳香氨基团;
Ar1与Ar2相同。
所述发光材料包括以下化合物中的一种或多种:
本发明的有益效果:本发明提供的一种发光材料,结构单一,分子量确定,具有较好的溶解性及成膜性,且薄膜形态稳定;具有很高的分解温度和比较低的升华温度,容易升华成高纯度的发光材料,可应用于小分子有机发光二极管;通过改变连接的芳香胺基团,可进一步改善其物理特性,提升基于该发光材料的光电器件的性能。本发明提供的一种发光材料的制备方法,以间溴苯硫酚与2-氟-4-溴苄腈为起始原料,通过一系列的简单反应得到发光材料的中间体,最后通过乌尔曼反应或铃木反应得到发光材料,步骤简单,产率高。本发明提供的一种有机发光二极管,发光层含有上述发光材料,具有较高的发光效率与稳定性。
为了能更进一步了解本发明的特征以及技术内容,请参阅以下有关本发明的详细说明与附图,然而附图仅提供参考与说明用,并非用来对本发明加以限制。
附图说明
下面结合附图,通过对本发明的具体实施方式详细描述,将使本发明的技术方案及其它有益效果显而易见。
附图中,
图1为本发明的发光材料的制备方法的流程图;
图2为本发明的有机发光二极管的结构示意图。
具体实施方式
为更进一步阐述本发明所采取的技术手段及其效果,以下结合本发明的优选实施例及其附图进行详细描述。
本发明首先提供一种发光材料,其结构通式为其中,Ar1、Ar2分别选自式(1)、式(2)、式(3)、式(4)、式(5)、式(6)、式(7)所示的芳香氨基团;
优选的,Ar1与Ar2相同。
具体的,所述发光材料包括以下化合物中的一种或多种:
上述发光材料,结构单一,分子量确定,具有较好的溶解性及成膜性,且薄膜形态稳定;具有很高的分解温度和比较低的升华温度,容易升华成高纯度的发光材料,可应用于小分子有机发光二极管;通过改变连接的芳香胺基团,可进一步改善其物理特性,提升基于该发光材料的光电器件的性能。
请参阅图1,本发明还提供一种上述发光材料的制备方法,包括如下步骤:
步骤1、制备中间体
所述中间体的合成路线为:
具体的,所述步骤1包括:
步骤11、间溴苯硫酚与2-氟-4-溴苄腈反应得到(b1)。
所述步骤11的具体实施步骤为:
于250ml三口烧瓶中将0.73g(30mmol)NaH缓慢加入到溶解有4.7g(25mmol)间溴苯硫酚的20ml干燥二甲基甲酰胺(DMF)中,然后向其中滴加溶解有5g(25mmol)2-氟-4-溴苄腈的20ml干燥二甲基甲酰胺中。在氮气保护下,加热回流反应20h,反应结束后降至室温,将反应液倒入50ml1M的NaOH溶液中,二氯甲烷(DCM)萃取,减压出掉溶剂,过硅胶柱,得到白色固体5.2g,即为化合物b1。分子式:C13H7Br2NS,MS:366.87,元素分析:C,42.31;H,1.91;Br,43.30;N,3.80;S,8.69。
步骤12、先在碱性条件下水解,再酸化,得到(b2)。
所述步骤12的具体实施步骤为:
于250ml三口烧瓶中加入80ml去离子水、15g KOH、及80ml乙醇,将5.2g化合物b1加入到反应瓶中,氮气保护下回流过夜。反应完冷却至室温,将反应液加入到100ml 6M的盐酸中,冰浴析出白色固体抽滤,干燥得到白色固体5.1g,即为化合物b2。分子式:C13H8Br2O2S,MS:385.86,元素分析:C,40.23;H,2.08;Br,41.18;O,8.25;S,8.26。
步骤13、发生脱水缩合反应,得到和中间体
所述步骤13的具体实施步骤为:
在500ml单口烧瓶中加入2.75g(10mmol)化合物b2,加入500ml氯仿作为溶剂,滴加3.2g(20mmol,2equ)三氟乙酸酐,室温搅拌10min,加冰浴冷却10min,然后加入0.5g三氟化硼乙醚,去掉冰浴室温反应12h。反应完,加亚硫酸钠饱和水溶液,淬灭多余的三氟乙酸酐,分液,减压蒸馏除掉溶剂,过柱分别得到和中间体产率分别为36%和45%。
步骤2、中间体与芳香胺化合物通过乌尔曼反应或铃木(Suzuki)反应得到发光材料其中,Ar1、Ar2分别选自式(1)、式(2)、式(3)、式(4)、式(5)、式(6)、式(7)所示的芳香氨基团;
优选的,Ar1与Ar2相同。
具体的,所述发光材料包括以下化合物中的一种或多种:
具体的,所述步骤2中,所述芳香胺化合物包括咔唑、二苯胺、9,9-二甲基吖啶、对咔唑苯硼酸酯、对苯基咔唑硼酸酯、对三苯胺硼酸酯、及对苯基吩噻嗪-S,S-二氧硼酸酯中的一种或多种;
所述咔唑的结构式为
所述二苯胺的结构式为
所述9,9-二甲基吖啶的结构式为
所述对咔唑苯硼酸酯的结构式为
所述对苯基咔唑硼酸酯的结构式为
所述对三苯胺硼酸酯的结构式为
所述对苯基吩噻嗪-S,S-二氧硼酸酯的结构式为以下结合具体实施例,详细说明所述步骤2的具体实施方法。
实施例1:中间体与咔唑通过乌尔曼反应得到反应式如下:
具体实施步骤为:
在氮气保护下,向三口烧瓶中加入100ml甲苯、0.72g(2mmol)中间体0.67g(4mmol)咔唑,在搅拌下加入0.3g叔丁基醇钠,再加入20mg三(二亚苄基丙酮)二钯(Pd2(dba)3),再加入0.3ml 10%三叔丁基膦正己烷溶液,加热回流,反应过夜。降温,用二氯甲烷萃取有机相,旋干,过柱。得白色固体产物0.70g,产率65%。分子式:C37H22N2OS;M/Z=542.15;理论值:542.15(100.0%),543.15(40.3%),544.15(8.7%),544.14(4.5%),545.14(1.8%),543.14(1.5%),545.16(1.0%);元素分析:C,81.89;H,4.09;N,5.16;O,2.95;S,5.91。
实施例2:中间体与9,9-二甲基吖啶通过乌尔曼反应得到反应式如下:
具体实施步骤为:
在氮气保护下,向三口烧瓶中加入100ml甲苯、0.72g(2mmol)中间体0.84g(4mmol)9,9-二甲基吖啶,在搅拌下加入0.3g叔丁基醇钠,再加入20mg三(二亚苄基丙酮)二钯(Pd2(dba)3),再加入0.3ml 10%三叔丁基膦正己烷溶液,加热回流,反应过夜。降温,用二氯甲烷萃取有机相,旋干,过柱。得到白色固体0.70g,产率56%。分子式:C43H34N2OS;M/Z=626.24;理论值:626.24(100.0%),627.24(48.1%),628.25(10.8%),628.23(4.5%),629.24(2.2%),629.25(1.8%);元素分析:C,82.40;H,5.57;N,4.47;O,2.55;S,5.12。
实施例3:中间体与二苯胺通过乌尔曼反应得到反应式如下:
具体实施步骤为:
在氮气保护下,向三口烧瓶中加入100ml甲苯、0.72g(2mmol)中间体0.84g(4mmol)的二苯胺,在搅拌下加入0.3g叔丁基醇钠,再加入20mg三(二亚苄基丙酮)二钯(Pd2(dba)3),再加入0.3ml 10%三叔丁基膦正己烷溶液,加热回流,反应过夜。降温,用二氯甲烷萃取有机相,旋干,过柱。得白色固体产物0.60g,产率55%。分子式:C37H26N2OS;M/Z=546.18;理论值:546.18(100.0%),547.18(41.2%),548.18(8.6%),548.17(4.5%),549.18(2.0%),549.19(1.0%);元素分析:C,81.29;H,4.79;N,5.12;O,2.93;S,5.87。
实施例4:中间体与对咔唑苯硼酸酯通过铃木反应得到反应式如下:
具体实施步骤为:
在氮气气氛下,往250ml烧瓶中加入96ml甲苯、32ml乙醇、16ml 2M的碳酸钾水溶液、0.72g(2mmol)中间体2.06g(1.2equ)对咔唑苯硼酸酯,室温搅拌,然后加入100mg三苯基磷钯(催化剂),96℃回流24小时。冷却至室温,二氯甲烷萃取,无水硫酸镁干燥。得白色固体产物1.18g,产率85%。分子式:C49H30N2OS;M/Z=694.21;理论值:694.21(100.0%),695.21(54.2%),696.21(14.8%),696.20(4.5%),697.21(2.6%),697.22(2.5%);元素分析:C,84.70;H,4.35;N,4.03;O,2.30;S,4.61。
实施例5:中间体与对苯基咔唑硼酸酯通过铃木反应得到反应式如下:
具体实施步骤为:
在氮气气氛下,往250ml烧瓶中加入96ml甲苯、32ml乙醇、16ml 2M的碳酸钾水溶液、0.72g(2mmol)中间体2.32g(1.2equ)对苯基咔唑硼酸酯,室温搅拌,然后加入100mg三苯基磷钯(催化剂),96℃回流24小时。冷却至室温,二氯甲烷萃取,无水硫酸镁干燥。分离得白色固体1.15g,产率83%。分子式:C49H30N2OS;M/Z=694.21;理论值:694.21(100.0%),695.21(54.2%),696.21(14.8%),696.20(4.5%),697.21(2.6%),697.22(2.5%);元素分析:C,84.70;H,4.35;N,4.03;O,2.30;S,4.61。
实施例6:中间体与对三苯胺硼酸酯通过铃木反应得到反应式如下:
具体实施步骤为:
在氮气气氛下,往250ml烧瓶中加入96ml甲苯、32ml乙醇、16ml 2M的碳酸钾水溶液、0.72g(2mmol)中间体2.32g(1.2equ)对三苯胺硼酸酯,室温搅拌,然后加入100mg三苯基磷钯(催化剂),96℃回流24小时。冷却至室温,二氯甲烷萃取,无水硫酸镁干燥。得白色固体产物1.16g,产率83%。分子式:C49H34N2OS;M/Z=698.24;理论值:698.24(100.0%),699.24(54.6%),700.25(14.0%),700.23(4.5%),701.25(2.6%),701.24(2.5%),700.24(1.0%);元素分析:C,84.21;H,4.90;N,4.01;O,2.29;S,4.59。
实施例7:中间体与对苯基吩噻嗪-S,S-二氧硼酸酯通过铃木反应得到反应式如下:
具体实施步骤为:
在氮气气氛下,往250ml烧瓶中加入96ml甲苯、32ml乙醇、16ml 2M的碳酸钾水溶液、0.72g(2mmol)中间体2.06g(1.2equ)对苯基吩噻嗪-S,S-二氧硼酸酯,室温搅拌,然后加入100mg三苯基磷钯(催化剂),96℃回流24小时。冷却至室温,二氯甲烷萃取,无水硫酸镁干燥。得白色固体产物1.40g,产率85%。分子式:C49H30N2O5S3;M/Z=822.13;理论值:822.13(100.0%),823.14(53.5%),824.13(15.3%),824.14(15.1%),825.13(7.5%),825.14(3.4%),823.13(3.1%),826.13(2.2%);元素分析:C,71.51;H,3.67;N,3.40;O,9.72;S,11.69。
上述发光材料的制备方法,以间溴苯硫酚与2-氟-4-溴苄腈为起始原料,通过一系列的简单反应得到发光材料的中间体,最后通过乌尔曼反应或铃木反应得到发光材料,步骤简单,产率高。
请参阅图2,本发明还提供一种含有上述发光材料的有机发光二极管,包括基板10、在基板10上从下到上依次层叠设置的阳极20、空穴注入层30、空穴传输层40、发光层50、电子传输层60、电子注入层70、及阴极80;
所述发光层50包括发光材料,所述发光材料的结构通式为
其中,Ar1、Ar2分别选自式(1)、式(2)、式(3)、式(4)、式(5)、式(6)、式(7)所示的芳香氨基团;
优选的,Ar1与Ar2相同。
具体的,所述发光材料包括以下化合物中的一种或多种:
优选的,所述发光层50中,所述发光材料的质量百分比为1%。
具体的,所述发光层50可以发红光、黄光、绿光、或者蓝光。
具体的,所述阳极20的材料包括透明金属氧化物,所述透明金属氧化物优选为氧化铟锡(ITO)。
具体的,所述空穴注入层30的材料包括2,3,6,7,10,11-六氰基-1,4,5,8,9,12-六氮杂三亚苯(HAT-CN),所述2,3,6,7,10,11-六氰基-1,4,5,8,9,12-六氮杂三亚苯的结构式为
具体的,所述空穴传输层40的材料包括1,1-双[(二-4-甲苯基氨基)苯基]环己烷(TAPC),所述1,1-双[(二-4-甲苯基氨基)苯基]环己烷的结构式为
具体的,所述发光层50还包括4,4'-双(N-咔唑)-1,1'-联苯(CBP),所述4,4'-双(N-咔唑)-1,1'-联苯的结构式为
具体的,所述电子传输层60的材料包括1,3,5-三[(3-吡啶基)-3-苯基]苯(TmPyPB),所述1,3,5-三[(3-吡啶基)-3-苯基]苯的结构式为
具体的,所述电子注入层70的材料包括氟化锂(LiF)。
具体的,所述阴极80的材料包括铝(Al)。
优选的,所述阳极20的厚度为95nm,所述空穴注入层30的厚度为5nm,所述空穴传输层40的厚度为20nm,所述发光层50的厚度为35nm,所述电子传输层60的厚度为55nm,所述电子注入层70的厚度为1nm,所述阴极80的厚度大于80nm。
所述有机发光二极管的制备过程如下:将氧化铟锡透明导电玻璃在清洗剂中进行超声处理,再用去离子水清洗,在丙酮/乙醇的混合溶剂中利用超声除油,之后在洁净的环境下烘烤至完全除去水分,然后用紫外光和臭氧进行清洗,并用低能阳离子轰击得到阳极20,将带有阳极20的透明导电玻璃置于真空腔内,抽真空至1×10-5~9×10-3Pa,然后在所述阳极20上依次蒸镀空穴注入层30、空穴传输层40、数层发光层50、电子传输层60、电子注入层70与阴极80,最终得到本实施例的有机发光二极管。
综上所述,本发明提供的一种发光材料,结构单一,分子量确定,具有较好的溶解性及成膜性,且薄膜形态稳定;具有很高的分解温度和比较低的升华温度,容易升华成高纯度的发光材料,可应用于小分子有机发光二极管;通过改变连接的芳香胺基团,可进一步改善其物理特性,提升基于该发光材料的光电器件的性能。本发明提供的一种发光材料的制备方法,以间溴苯硫酚与2-氟-4-溴苄腈为起始原料,通过一系列的简单反应得到发光材料的中间体,最后通过乌尔曼反应或铃木反应得到发光材料,步骤简单,产率高。本发明提供的一种有机发光二极管,发光层含有上述发光材料,具有较高的发光效率与稳定性。
以上所述,对于本领域的普通技术人员来说,可以根据本发明的技术方案和技术构思作出其他各种相应的改变和变形,而所有这些改变和变形都应属于本发明权利要求的保护范围。
Claims (10)
1.一种发光材料,其特征在于,结构通式为其中,Ar1、Ar2分别选自式(1)、式(2)、式(3)、式(4)、式(5)、式(6)、式(7)所示的芳香氨基团;
2.如权利要求1所述的发光材料,其特征在于,Ar1与Ar2相同。
3.如权利要求2所述的发光材料,其特征在于,包括以下化合物中的一种或多种:
4.一种发光材料的制备方法,其特征在于,包括如下步骤:
步骤1、制备中间体
步骤2、中间体与芳香胺化合物通过乌尔曼反应或铃木反应得到发光材料,所述发光材料的结构通式为其中,Ar1、Ar2分别选自式(1)、式(2)、式(3)、式(4)、式(5)、式(6)、式(7)所示的芳香氨基团;
5.如权利要求4所述的发光材料的制备方法,其特征在于,Ar1与Ar2相同。
6.如权利要求5所述的发光材料的制备方法,其特征在于,所述发光材料包括以下化合物中的一种或多种:
7.如权利要求4所述的发光材料的制备方法,其特征在于,所述步骤1包括:
步骤11、间溴苯硫酚与2-氟-4-溴苄腈反应得到
步骤12、先在碱性条件下水解,再酸化,得到
步骤13、发生脱水缩合反应,得到和中间体
8.一种有机发光二极管,其特征在于,包括基板(10)、在基板(10)上从下到上依次层叠设置的阳极(20)、空穴注入层(30)、空穴传输层40)、发光层(50)、电子传输层(60)、电子注入层(70)、及阴极(80);
所述发光层(50)包括发光材料,所述发光材料的结构通式为
其中,Ar1、Ar2分别选自式(1)、式(2)、式(3)、式(4)、式(5)、式(6)、式(7)所示的芳香氨基团;
9.如权利要求8所述的有机发光二极管,其特征在于,Ar1与Ar2相同。
10.如权利要求9所述的有机发光二极管,其特征在于,所述发光材料包括以下化合物中的一种或多种:
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CN113004259A (zh) * | 2019-12-20 | 2021-06-22 | 江苏三月光电科技有限公司 | 一种以蒽酮骨架为核心的化合物及其应用 |
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