CN112079876B - Organic compound and organic electroluminescent device using same - Google Patents
Organic compound and organic electroluminescent device using same Download PDFInfo
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- CN112079876B CN112079876B CN202010938466.1A CN202010938466A CN112079876B CN 112079876 B CN112079876 B CN 112079876B CN 202010938466 A CN202010938466 A CN 202010938466A CN 112079876 B CN112079876 B CN 112079876B
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 20
- 239000010410 layer Substances 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 14
- 238000002347 injection Methods 0.000 claims description 8
- 239000007924 injection Substances 0.000 claims description 8
- 239000012044 organic layer Substances 0.000 claims description 8
- 230000005525 hole transport Effects 0.000 claims description 6
- 239000002019 doping agent Substances 0.000 claims description 4
- 230000000903 blocking effect Effects 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 16
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 8
- 125000003118 aryl group Chemical group 0.000 abstract description 4
- 229910052799 carbon Inorganic materials 0.000 abstract description 4
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 4
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 abstract description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 abstract description 2
- 125000002252 acyl group Chemical group 0.000 abstract description 2
- 125000003342 alkenyl group Chemical group 0.000 abstract description 2
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 2
- 125000000304 alkynyl group Chemical group 0.000 abstract description 2
- -1 amino, silyl Chemical group 0.000 abstract description 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract description 2
- 125000004104 aryloxy group Chemical group 0.000 abstract description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract description 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
- 229910052805 deuterium Inorganic materials 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 125000004404 heteroalkyl group Chemical group 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 2
- 150000002431 hydrogen Chemical class 0.000 abstract description 2
- 239000001257 hydrogen Substances 0.000 abstract description 2
- 150000002527 isonitriles Chemical class 0.000 abstract description 2
- 150000002825 nitriles Chemical class 0.000 abstract description 2
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 abstract description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 abstract description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 abstract description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract description 2
- 229910052717 sulfur Inorganic materials 0.000 abstract description 2
- 229920001621 AMOLED Polymers 0.000 abstract 1
- 239000000758 substrate Substances 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000001819 mass spectrum Methods 0.000 description 16
- 238000005259 measurement Methods 0.000 description 16
- 239000011521 glass Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 239000011368 organic material Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000010405 anode material Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- 229940093475 2-ethoxyethanol Drugs 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 229940126208 compound 22 Drugs 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- VVOLVFOSOPJKED-UHFFFAOYSA-N copper phthalocyanine Chemical compound [Cu].N=1C2=NC(C3=CC=CC=C33)=NC3=NC(C3=CC=CC=C33)=NC3=NC(C3=CC=CC=C33)=NC3=NC=1C1=CC=CC=C12 VVOLVFOSOPJKED-UHFFFAOYSA-N 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- MJRFDVWKTFJAPF-UHFFFAOYSA-K trichloroiridium;hydrate Chemical compound O.Cl[Ir](Cl)Cl MJRFDVWKTFJAPF-UHFFFAOYSA-K 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
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- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/002—Heterocyclic compounds
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- 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
- 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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- 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
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- H—ELECTRICITY
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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
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
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- Electroluminescent Light Sources (AREA)
Abstract
The invention provides an organic compound and application thereof, and relates to the technical field of organic photoelectric materials. The structural formula of the organic compound obtained by the invention is an organic compound represented by the following formula (I):
wherein R is 1 To R 10 Independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof; x is selected from O, S, se, C (R) 11 R 12 )、NR 11 、Si(R 11 R 12 )；R 11 And R is 12 Selected from the group consisting of substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl; x is X 1 —X 9 Selected from carbon or nitrogen. The organic compound can be used as a luminescent doping material in an organic electroluminescent device, can effectively improve the luminescent efficiency of the OLED device, has long service life, and has the prospect of being applied to the AMOLED industry.
Description
Technical Field
The invention belongs to the field of organic electroluminescence, and in particular relates to an organic electroluminescent device, an organic compound and an organic electroluminescent device using the same.
Background
In recent years, as the size of display devices becomes larger, flat panel display devices that occupy less space have been increasingly demanded. The flat panel display device includes an organic electroluminescent device, also referred to as an organic electroluminescent diode (OLED). The technology of the organic electroluminescent device is being developed at a great speed.
When electrons and holes are respectively injected into the electron and hole transport layers from the cathode and the anode, the electrons and the holes respectively migrate to the light emitting layer through the electron and hole transport layers and meet in the light emitting layer to form excitons and excite the light emitting molecules, and redundant energy is released in the form of photons.
The organic electroluminescent device may be formed on a flexible transparent substrate such as plastic. The organic electroluminescent device may also be driven at a lower voltage (i.e., a voltage less than or equal to 10V) than that required in a plasma display panel or an inorganic Electroluminescent (EL) display. The organic electroluminescent device is advantageous in that it consumes less power and provides excellent color display as compared to other display devices. Also, pictures can be reproduced using three colors (i.e., green, blue, and red), so the organic electroluminescent device is widely regarded as a next-generation color display device.
The process of manufacturing an organic Electroluminescent (EL) device is described as follows:
(1) An anode material is coated on a transparent substrate. Indium Tin Oxide (ITO) is generally used as the anode material.
(2) A Hole Injection Layer (HIL) was evaporated on the anode material. The hole injection layer is formed of a 2-TNATA layer having a thickness of 10 nanometers (nm) to 60 (nm).
(3) A Hole Transport Layer (HTL) is then evaporated. The hole transport layer is mainly formed by 4,4' -bis [ N- (1-naphthyl) -N-phenylamino ] biphenyl (NPB), and the thickness of the hole transport layer is 30-60 nanometers (nm) in a common evaporation and coating mode.
(4) Thereafter, an organic light emitting layer is formed. If doping is desired, a dopant may be added. In the case of luminescence, the organic light-emitting layer is typically evaporated to a thickness of 30 nanometers (nm) to 60 nanometers (nm).
(5) An Electron Transport Layer (ETL) and an Electron Injection Layer (EIL) are sequentially formed on the organic light emitting layer, or the electron injection and transport layers are formed on the organic light emitting layer to be used together by vapor deposition.
(6) Finally, a cathode layer is coated, and a protective layer is coated on the cathode.
Light emitting devices that emit (or display) blue, green, and red colors are fabricated in accordance with the method of forming a light emitting layer in the above structure. As a light emitting material, excitons are formed by recombination of electrons and holes injected from each electrode. Singlet excitons emit fluorescence and triplet excitons emit phosphorescence. Singlet excitons emitting fluorescence have a formation probability of 25%, whereas triplet excitons emitting phosphorescence have a formation probability of 75%. Thus, triplet excitons provide greater luminous efficiency than singlet excitons. Such organic materials may have greater luminous efficiency than fluorescent materials.
When such an organic material is used, high luminous efficiency, high color purity, and prolonged durability are required. When an organic material is used, the X value of CIE chromaticity coordinates becomes larger and visibility decreases as color purity increases, resulting in difficulty in providing high luminous efficiency. Accordingly, there is a need to develop organic materials that provide excellent chromaticity coordinates, improved luminous efficiency, and extended durability.
Disclosure of Invention
An object of the present invention is to provide an organic compound and an organic electroluminescent device using the same that solve one or more problems due to the limitations and disadvantages of the related art.
Another object of the present invention is to provide an organic electroluminescent device having high color purity, high luminance and long durability by using a compound represented by formula (I) and the compound as a dopant in a light emitting layer of the organic electroluminescent device.
The object of the present invention can be achieved by providing an organic compound represented by the following formula (I).
An organic compound represented by the following formula (I):
wherein R is 1 To R 10 Independently selected from the group consisting of hydrogen, deuterium, halogen, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acid, ester, nitrile, isonitrile, thio, sulfinyl, sulfonyl, phosphino, and combinations thereof;
x is selected from O, S, se, C (R) 11 R 12 )、NR 11 、Si(R 11 R 12 )；
Preferably, R 11 And R is 12 Selected from the group consisting of substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C2-C30 heteroaryl;
X 1 —X 9 selected from carbon or nitrogen.
Preferably, the L A The group is selected from one of the following structural formulas:
preferably, the L B The group is selected from one of the following structural formulas:
preferably, said compound of the invention is selected from organic compounds of the following structure:
the invention also provides an organic electroluminescent device, which comprises a cathode layer, an anode layer and an organic layer, wherein the organic layer comprises at least one layer of a hole injection layer, a hole transmission layer, a luminescent layer, a hole blocking layer, an electron injection layer and an electron transmission layer, and is characterized in that: the at least one organic compound layer comprises at least one organic compound according to the invention.
The organic compound is used as a doping agent in a light-emitting layer of an organic electroluminescent device.
The organic electroluminescent device is applied to an Organic Light Emitting Device (OLED), an Organic Solar Cell (OSC), electronic Paper (e-Paper), an Organic Photoconductor (OPC) or an Organic Thin Film Transistor (OTFT).
Drawings
The accompanying drawings, which are included to provide a further understanding of the invention, illustrate embodiments of the invention and together with the description serve to explain the principle of the invention.
In the drawings of which there are shown,
fig. 1 illustrates a graph showing that visibility decreases as the color purity of the organic electroluminescent device increases (i.e., as the X value of chromaticity coordinates becomes larger).
FIG. 2 illustrates the structural formulas of copper (II) phthalocyanine (2-TNATA, NPB, ir (ppy) 3, GH-1, GH-2, and Alq 3) compounds used in embodiments of the invention.
Detailed Description
Reference will now be made in detail to the preferred embodiments of the present invention, examples of which are illustrated in the accompanying drawings.
The method of forming the organic compound according to the present invention is described below.
Example 1: synthesis of C-1
1. Synthesis of intermediate L-1:
step 2L-1-3 (5.6 g,19.1 mmol) and 180mL of methylene chloride were added to a 1L round bottom flask and stirred at ambient temperature. Bromine (3.4 mL,66 mmol) was diluted and added dropwise to 50mL of methylene chloride, and the mixture was stirred at room temperature for 8 hours, and after the completion of the reaction, 100mL of acetone was added to the reaction vessel and stirred. The resulting solid was filtered and then washed with acetone. The solid was recrystallized from monochlorobenzene to give intermediate L-1-2 (6.4 g, 75%). Mass spectrum m/z: theoretical value: 450.12; actual measurement value: 48.91.
step 3L-1-2 (4.5 g,10 mmol) and tetrahydrofuran (180 mL) were added to a 1L round bottom flask under nitrogen and stirred at ambient temperature. N-butyllithium (4.4 mL,11 mmol) was slowly added dropwise at-78deg.C, methyl bromide-D3 (1.4 g,11 mmol) was added dropwise after half an hour and stirred for 2 hours, and water was added to stop the reaction after stirring for another 4 hours at room temperature. Extracted with dichloromethane and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give crude product which was passed through a silica gel column to give intermediate L-1-1 (3.5 g, 90%). Mass spectrum m/z: theoretical value: 388.27; actual measurement value: 387.03.
step 4L-1-1 (16.2 g,41.8 mmol), A (12.0 g,41.8 mmol), potassium carbonate (11.7 g,104.6 mmol), tetrakis triphenylphosphine palladium (2.4 g,2.1 mmol), 1, 4-dioxane (140 mL) and water (70 mL) were added to a 500mL reaction flask. The reaction system is heated to 60 ℃ and reacted for ten hours under the protection of nitrogen. The reaction solution was poured into 450mL of methanol, and the precipitated solid was filtered. The precipitated solid was dissolved in chlorobenzene, and filtered through a funnel containing celite and silica gel powder. The orange liquid obtained by filtration was concentrated to dryness and recrystallized from methanol to give intermediate L-1 (12.5 g, yield 65%). Mass spectrum m/z: theoretical value: 458.60; actual measurement value: 458.24.
synthesis of a dichloro-crosslinked dimer Complex of C-1
A mixed solution of iridium trichloride monohydrate (3 g,10 mmol), ligand L-2 (4.3 g,22.1 mmol) and a ratio of diethyl ether to distilled water of 3:1 (120 mL:40 mL) was added to a dry two-necked round bottom flask, heated under reflux for 24 hours, then an appropriate amount of distilled water was added, the precipitated solid was filtered again, and the solid was washed with methanol and petroleum ether to give a dichloro-crosslinked dimer complex of C-1 (3.7 g, yield: 61%). Mass spectrum m/z: theoretical value: 1218.03; actual measurement value: 1218.65. the above results confirm that the obtained product was the target product.
3. Synthesis of intermediate I-1
In a round bottom flask, dichloro-crosslinked dimer complex (3.4 g,2.8 mmol) was dissolved in 200mL dichloromethane. In another flask, silver (I) triflate (1.6 g,6.1 mmol) was dissolved in 100 mM MeOH. It was slowly added to the dimer solution with continuous stirring at room temperature. The reaction was stirred overnight in the dark and then filtered through celite to remove silver chloride precipitate. The solvent was removed under reduced pressure to give intermediate I-1 (4.0 g, yield: 91%) which was used without further purification. Mass spectrum m/z: theoretical value: 785.71; actual measurement value: 786.33. the above results confirm that the obtained product was the target product.
Synthesis of C-1
Intermediate I-1 (4.3 g,5.5 mmol) and ligand L-1 (7.6 g,16.6 mmol) were dissolved in a mixed solvent of DMF (100 mL) and 2-ethoxyethanol (100 mL) and heated at 130℃for 18 hours. After evaporation of the solvent, the crude product was purified by column chromatography using a hexane eluent containing 65-100% of methylene chloride to give C-1 (2.7 g, yield: 47%). Mass spectrum m/z: theoretical value: 1030.15; actual measurement value: 1030.29.
example 2:
example 2: synthesis of C-15
1. Synthesis of intermediate L-2:
step 2L-15-4 (13.7 g,41.8 mmol), L-15-3 (9.2 g,41.8 mmol), potassium carbonate (11.7 g,104.6 mmol), palladium tetraphenylphosphine (2.4 g,2.1 mmol), 1, 4-dioxane (140 mL) and water (70 mL) were added to a 500mL reaction flask. The reaction system is heated to 60 ℃ and reacted for ten hours under the protection of nitrogen. The reaction solution was poured into 450mL of methanol, and the precipitated solid was filtered. The precipitated solid was dissolved in chlorobenzene, and filtered through a funnel containing celite and silica gel powder. The orange liquid obtained by filtration was concentrated to dryness and recrystallized from methanol to give intermediate L-15-2 (9.6 g, yield 60%). Mass spectrum m/z: theoretical value: 383.44; actual measurement value: 383.13.
step 3L-1-2 (7.3 g,19.1 mmol) and 180mL of methylene chloride were added to a 1L round bottom flask and stirred at ambient temperature. Bromine (1.7 mL,33 mmol) was diluted and added dropwise to 50mL of methylene chloride, followed by stirring at room temperature for 8 hours, and after the completion of the reaction, 100mL of acetone was added to the reaction vessel and stirred. The resulting solid was filtered and then washed with acetone. The solid was recrystallized from monochlorobenzene to give intermediate L-1-1 (6.2 g, 70%). Mass spectrum m/z: theoretical value: 462.34; actual measurement value: 461.04.
step 4L-1-1 (4.6 g,10 mmol) and tetrahydrofuran (180 mL) were added to a 1L round bottom flask under nitrogen and stirred at ambient temperature. N-butyllithium (4.4 mL,11 mmol) was slowly added dropwise at-78deg.C, methyl bromide-D3 (1.4 g,11 mmol) was added dropwise after half an hour and stirred for 2 hours, and water was added to stop the reaction after stirring for another 4 hours at room temperature. Extracted with dichloromethane and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and recrystallized to give crude product which was passed through a silica gel column to give intermediate L-1 (3.6 g, 89%). Mass spectrum m/z: theoretical value: 400.49; actual measurement value: 400.17.
synthesis of C-15
Intermediate I-1 (4.3 g,5.5 mmol) and ligand L-15 (6.6 g,16.6 mmol) were dissolved in a mixed solvent of DMF (100 mL) and 2-ethoxyethanol (100 mL) and heated at 130℃for 18 hours. After evaporation of the solvent, the crude product was purified by column chromatography using a hexane eluent containing 65-100% of methylene chloride to give C-15 (2.45 g, yield: 45%). Mass spectrum m/z: theoretical value: 972.21; actual measurement value: 972.03.
example 3: preparation of Compound 22
The synthetic procedure of example 1 gave compound 22. Mass spectrum m/z, theoretical value: 1208.30; actual measurement value: 1208.02.
example 4: preparation of Compound 108
The synthetic procedure of example 1 was followed to give compound 108. Mass spectrum m/z, theoretical value: 957.21; actual measurement value: 957.35.
example 5: preparation of Compound 119
The synthesis of example 1 gave compound 119. Mass spectrum m/z, theoretical value: 1106.29; actual measurement value: 1106.26.
example 6: preparation of Compound 134
The synthetic procedure of example 1 was followed to give compound 134. Mass spectrum m/z, theoretical value: 1022.23; actual measurement value: 1022.35.
device example 1
The ITO glass substrate was patterned to have a light emitting region of 3mm×3 mm. Then, the patterned ITO glass substrate was washed. The substrate is then placed in a vacuum chamber. Standard pressure is set to 1×10 -6 And (5) a bracket. Thereafter, on the ITO substrate
And->
Sequentially forming layers of organic material.
Device example 2
The ITO glass substrate was patterned to have a light emitting region of 3mm×3 mm. Then, the patterned ITO glass substrate was washed. The substrate is then placed in a vacuum chamber. Standard pressure is set to 1×10 -6 And (5) a bracket. Thereafter, on the ITO substrate
And->
Sequentially forming layers of organic material.
Device example 3
The ITO glass substrate was patterned to have a light emitting region of 3mm×3 mm. Then, the patterned ITO glass substrate was washed. The substrate is then placed in a vacuum chamber. Standard pressure is set to 1×10 -6 And (5) a bracket. Thereafter, on the ITO substrate
And->
Sequentially forming layers of organic material.
Device example 4
The ITO glass substrate was patterned to have a light emitting region of 3mm×3 mm. Then, the patterned ITO glass substrate was washed. The substrate is then placed in a vacuum chamber. Standard pressure is set to 1×10 -6 And (5) a bracket. Thereafter, on the ITO substrate
And->
Sequentially forming layers of organic material.
Device example 5
The ITO glass substrate was patterned to have a light emitting region of 3mm×3 mm. Then, the patterned ITO glass substrate was washed. The substrate is then placed in a vacuum chamber. Standard pressure is set to 1×10 -6 And (5) a bracket. Thereafter, on the ITO substrate
And->
Sequentially forming layers of organic material.
Device example 6
The ITO glass substrate was patterned to have a light emitting region of 3mm×3 mm. Then, the patterned ITO glass substrate was washed. The substrate is then placed in a vacuum chamber. Standard pressure is set to 1×10 -6 And (5) a bracket. Thereafter, on the ITO substrate
And->
Sequentially forming layers of organic material.
The structures of GH-1 and GH2 are as follows:
comparative example
The ITO glass substrate was patterned to have a light emitting region of 3mm×3 mm. Then, the patterned ITO glass substrate was washed. The substrate is then placed in a vacuum chamber. Standard pressure is set to 1×10 -6 And (5) a bracket. On an ITO substrate
And->
Sequentially forming layers of organic material.
The characteristics of voltage, efficiency according to the above examples and comparative examples are shown in table 1 below.
TABLE 1
As shown in table 1, the device operates with high efficiency at low voltage even when the color purity is high. And, the current efficiency of example 2 was increased by 20% or more as compared with the comparative example.
It will be apparent to those skilled in the art that many modifications and variations can be made to the present invention without departing from the spirit or scope of the invention. It is therefore contemplated that the present invention cover modifications and variations of the invention provided they fall within the scope of the appended claims and their equivalents.
Industrial applicability
The present invention provides an organic electroluminescent device having excellent color purity and brightness and prolonged durability by using a compound represented by formula (I) as a light emitting layer of the organic electroluminescent device.
Claims (5)
1. An organic compound represented by the following formula (I):
in the structure, L A Is a structure formed from a compound selected from the following formulas:
L B is a structure formed from a compound selected from the following formulas:
2. an organic compound characterized by: the organic compound is selected from the group consisting of compounds of the following structures:
3. an organic electroluminescent device comprising a cathode layer, an anode layer and an organic layer, wherein the organic layer comprises a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron injection layer and an electron transport layer, and is characterized in that: the light-emitting layer comprising at least one organic compound according to claim 1.
4. An organic electroluminescent device as claimed in claim 3, characterized in that the organic compound is used as a dopant in the light-emitting layer.
5. Use of an organic electroluminescent device according to claim 3 in an organic light emitting device, an organic solar cell, electronic paper, an organic photoreceptor or an organic thin film transistor.
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