WO2015085725A1 - 蒽类衍生物及制备方法、应用和有机发光器件 - Google Patents
蒽类衍生物及制备方法、应用和有机发光器件 Download PDFInfo
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- WO2015085725A1 WO2015085725A1 PCT/CN2014/078772 CN2014078772W WO2015085725A1 WO 2015085725 A1 WO2015085725 A1 WO 2015085725A1 CN 2014078772 W CN2014078772 W CN 2014078772W WO 2015085725 A1 WO2015085725 A1 WO 2015085725A1
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- Prior art keywords
- organic
- preparation
- following
- derivative
- organic light
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- 150000001454 anthracenes Chemical class 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 239000000463 material Substances 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 150000002894 organic compounds Chemical class 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- -1 substituted aryl diboronic acid compound Chemical class 0.000 claims description 5
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 238000005401 electroluminescence Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 3
- RZVHIXYEVGDQDX-UHFFFAOYSA-N 9,10-anthraquinone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1 RZVHIXYEVGDQDX-UHFFFAOYSA-N 0.000 claims description 2
- 150000004059 quinone derivatives Chemical class 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 150000004056 anthraquinones Chemical class 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 150000002475 indoles Chemical class 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 claims 1
- 239000010410 layer Substances 0.000 description 20
- 238000012360 testing method Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 230000005525 hole transport Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 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 2
- BODYVHJTUHHINQ-UHFFFAOYSA-N (4-boronophenyl)boronic acid Chemical compound OB(O)C1=CC=C(B(O)O)C=C1 BODYVHJTUHHINQ-UHFFFAOYSA-N 0.000 description 1
- HNGIZKAMDMBRKJ-UHFFFAOYSA-N 2-acetamido-3-(1h-indol-3-yl)propanamide Chemical compound C1=CC=C2C(CC(NC(=O)C)C(N)=O)=CNC2=C1 HNGIZKAMDMBRKJ-UHFFFAOYSA-N 0.000 description 1
- LOPWWCSLIWAJCY-UHFFFAOYSA-N C1(=CC=CC=C1)NC1=CC=C(C2=CC=C(NC3=CC=CC=C3)C=C2)C=C1.C1=CC=CC2=CC3=CC=CC=C3C=C12 Chemical compound C1(=CC=CC=C1)NC1=CC=C(C2=CC=C(NC3=CC=CC=C3)C=C2)C=C1.C1=CC=CC2=CC3=CC=CC=C3C=C12 LOPWWCSLIWAJCY-UHFFFAOYSA-N 0.000 description 1
- 229910019015 Mg-Ag Inorganic materials 0.000 description 1
- 241001602876 Nata Species 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 150000002290 germanium Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
Classifications
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/26—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms
- C07C1/30—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms by splitting-off the elements of hydrogen halide from a single molecule
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
- C07C1/321—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a non-metal atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/27—Polycyclic condensed hydrocarbons containing three rings
- C07C15/28—Anthracenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
- C07C17/02—Preparation of halogenated hydrocarbons by addition of halogens to unsaturated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- C07C2531/24—Phosphines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- 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]
- H10K50/17—Carrier injection layers
Definitions
- Organic electroluminescence generally consists of two opposed electrodes and at least one organic light-emitting compound interposed between the two electrodes. Charge is injected into the organic layer formed between the anode and the cathode to form electron and hole pairs, and the organic compound having fluorescent or phosphorescent characteristics is caused to emit light.
- the organic electroluminescent device is designed as a multilayer structure because the hole and electron movement speeds are different, and the hole injection layer, the hole transport layer, the electron transport layer, and the electron injection layer are appropriately designed, and the hole and the hole can be improved.
- the transmission efficiency of electrons equalizes holes and electrons in the device, thereby improving luminous efficiency.
- the basic structure of an OLED device was a simple structure of an anode (ITO), a hole transport layer (HTL), an emissive layer (EML), and a cathode (Mg: Ag). Subsequently, a hole injection layer such as copper phthalocyanine Cu.Pc, an electron injection layer (LiF), and a cathode (Al: Li) were added. Due to the insertion of a large number of organic layers, the structure of the OLED device becomes complicated and technically increased. However, for production, in order to reduce the number of production steps and improve power efficiency, it is desirable to reduce the number of layers.
- the inventors of the present invention have studied a novel asymmetric quinone derivative which can be used as a host material, a hole injecting material or a hole transporting material.
- the anthracene derivative can improve the luminous efficiency and the luminescent brightness, and greatly improve various aspects of the performance of the organic electroluminescent device.
- Step N3 filtering, washing to obtain the above, the aryl or substituted aryl diboronic acid compound is selected from at least the following
- the anthracene derivative is used as a fluorescent green host material in the organic electroluminescent device.
- the anthracene derivatives of the present invention can be used to fabricate organic light-emitting devices.
- the organic light emitting device includes a first electrode, a second electrode, and one or more organic compound layers interposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the germanium Class Derivatization
- the anthracene derivatives provided by the present invention have high luminous efficiency.
- the high luminous efficiency indicates that the compound can be used as a luminescent material or a luminescent host material, particularly as a fluorescent host material.
- the steroid also has a high glass transition temperature and is not easily crystallized, and can be used in an organic electroluminescent device, which exhibits high efficiency, high brightness, long life, and better charge transport capability, thereby prolonging organic electroluminescence.
- the lifetime of the light emitting device reduces the manufacturing cost of the organic electroluminescent device.
- the present invention provides an anthraquinone compound, a preparation method and an application thereof, and the present invention will be further described in detail below in order to clarify the object, the technical solution and the effect of the present invention. It is understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
- the present invention provides an anthraquinone compound represented by the following molecular formula:
- Step Nh is added to the degassed reaction vessel Solvent
- Step ⁇ 2 The reaction system is heated to 60 ⁇ to fully react;
- Step N3 Filter, Wash ⁇ /Get the place
- the aryl or substituted aryl diboronic acid compound is selected from at least one of the following
- the temperature in the reactor was raised to 70 ° C, and Pd(PPh 3 ) 4 (0, 35 g, 0.0003 mol) was added thereto, and 100 mL of distilled water was stirred and refluxed for 1 h. After full reaction.
- Test value is C: 94.76% H: 5.24%
- test value is C: 94.85%; H: 5, 15%;
- test value is C: 94.86%; B t 5.14%;
- test value is C: 94.92%; Hr 5.08%;
- test value is C : 92.47%; H: 4,91%;
- the present invention is exemplified by a fluorescent green host material as follows.
- the following compound a is used as a fluorescent green host material
- b is used as a fluorescent green doping material
- 2- ⁇ is used as a hole injecting layer material
- a-NPD(N,N'dinaphthyl-anthracene, anthracene-diphenylbenzidine As a hole transporting layer material, an organic light-emitting device of the following structure was fabricated to obtain Comparative Sample 1.
- a 2-nm NATA was vacuum-deposited on the substrate to form a hole injecting layer.
- a-NPD having a thickness of 30 nm was vacuum-deposited to form a hole transport layer.
- a compound represented by Chemical Formula a and a compound represented by Chemical Formula b (doping ratio: 3%) having a thickness of 30 nm were vacuum-deposited, and a light-emitting layer having a thickness of 30 nm was formed.
- An organic light-emitting device was fabricated by vacuum-depositing LiF 0.5 nm (electron injection) and Al 60 nm on the electron transport layer.
- the wavelength of the display shows that the illuminating color is green.
- the luminous efficiency and brightness of the samples 1-6 were significantly improved.
Landscapes
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US14/416,957 US20150380655A1 (en) | 2013-12-10 | 2014-05-29 | Anthracene derivative, method for preparing the same, use thereof and organic light emitting device |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201310670362.7A CN103664495B (zh) | 2013-12-10 | 2013-12-10 | 蒽类衍生物及制备方法、应用和有机发光器件 |
CN201310670362.7 | 2013-12-10 |
Publications (1)
Publication Number | Publication Date |
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WO2015085725A1 true WO2015085725A1 (zh) | 2015-06-18 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/CN2014/078772 WO2015085725A1 (zh) | 2013-12-10 | 2014-05-29 | 蒽类衍生物及制备方法、应用和有机发光器件 |
Country Status (3)
Country | Link |
---|---|
US (1) | US20150380655A1 (zh) |
CN (1) | CN103664495B (zh) |
WO (1) | WO2015085725A1 (zh) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN103664495B (zh) * | 2013-12-10 | 2016-07-06 | 京东方科技集团股份有限公司 | 蒽类衍生物及制备方法、应用和有机发光器件 |
CN108383693A (zh) * | 2018-02-06 | 2018-08-10 | 陕西师范大学 | 一种有机蓝色荧光材料及其制备方法和应用 |
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2013
- 2013-12-10 CN CN201310670362.7A patent/CN103664495B/zh active Active
-
2014
- 2014-05-29 US US14/416,957 patent/US20150380655A1/en not_active Abandoned
- 2014-05-29 WO PCT/CN2014/078772 patent/WO2015085725A1/zh active Application Filing
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CN101809117A (zh) * | 2007-11-01 | 2010-08-18 | 第一毛织株式会社 | 用于有机光电装置的材料及有机光电装置 |
CN103554011A (zh) * | 2013-10-30 | 2014-02-05 | 吉林奥来德光电材料股份有限公司 | 一种含蒽类衍生物、制备方法及其应用 |
CN103664495A (zh) * | 2013-12-10 | 2014-03-26 | 京东方科技集团股份有限公司 | 蒽类衍生物及制备方法、应用和有机发光器件 |
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