CN111978355A - Organic compound and organic electroluminescent device using the same - Google Patents
Organic compound and organic electroluminescent device using the same Download PDFInfo
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- CN111978355A CN111978355A CN202010938691.5A CN202010938691A CN111978355A CN 111978355 A CN111978355 A CN 111978355A CN 202010938691 A CN202010938691 A CN 202010938691A CN 111978355 A CN111978355 A CN 111978355A
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 6
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 claims abstract description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 3
- 125000002252 acyl group Chemical group 0.000 claims abstract description 3
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 3
- -1 amino, silyl Chemical group 0.000 claims abstract description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 3
- 150000002148 esters Chemical class 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- 125000004404 heteroalkyl group Chemical group 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 150000002527 isonitriles Chemical class 0.000 claims abstract description 3
- 150000002825 nitriles Chemical class 0.000 claims abstract description 3
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims abstract description 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims abstract description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 239000010410 layer Substances 0.000 claims description 54
- 150000001875 compounds Chemical class 0.000 claims description 11
- 238000002347 injection Methods 0.000 claims description 10
- 239000007924 injection Substances 0.000 claims description 10
- 239000012044 organic layer Substances 0.000 claims description 8
- 230000005525 hole transport Effects 0.000 claims description 7
- 239000002019 doping agent Substances 0.000 claims description 5
- 230000000903 blocking effect Effects 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 4
- 229920001621 AMOLED Polymers 0.000 abstract 1
- 229910052711 selenium Inorganic materials 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
- 239000011521 glass Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000011368 organic material Substances 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 238000003786 synthesis reaction Methods 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
- 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
- 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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-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
- 239000000203 mixture Substances 0.000 description 4
- 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 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
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000001308 synthesis method Methods 0.000 description 4
- 239000010405 anode material Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 238000000034 method Methods 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
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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
- 239000011248 coating agent Substances 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
- 239000012153 distilled water Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000001704 evaporation 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
- 229910052763 palladium Inorganic materials 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
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution 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
- 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
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 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
- 238000003756 stirring Methods 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- MJRFDVWKTFJAPF-UHFFFAOYSA-K trichloroiridium;hydrate Chemical compound O.Cl[Ir](Cl)Cl MJRFDVWKTFJAPF-UHFFFAOYSA-K 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- 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
- C07F15/0046—Ruthenium compounds
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- 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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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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- C09K2211/1007—Non-condensed systems
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- C09K2211/1018—Heterocyclic compounds
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- 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
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- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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- C09K2211/10—Non-macromolecular compounds
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- C09K2211/1096—Heterocyclic compounds characterised by ligands containing other heteroatoms
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- Chemical & Material Sciences (AREA)
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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 of the invention is represented by the following formula (I):
wherein R is1To R10Independently 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(R11R12)、NR11、Si(R11R12)；R11And R12Selected from substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl; x1—X9Selected from carbon or nitrogen. The organic compound is used as a light-emitting doping material in an organic electroluminescent device, can effectively improve the light-emitting efficiency of the OLED device, has long service life, and has a prospect of being applied to the AMOLED industry.
Description
Technical Field
The present invention relates to an organic electroluminescent device, and more particularly, to an organic compound and an organic electroluminescent device using the same. Most particularly, the present invention relates to a phosphor used as a dopant of a light emitting layer of an organic electroluminescent device formed by sequentially evaporating an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and a cathode.
Background
In recent years, flat panel display devices that occupy less space have been increasingly demanded as the size of the display devices has become larger. The flat panel display device includes an organic electroluminescent device, also called an Organic Light Emitting Diode (OLED). The technology of the organic electroluminescent device is being developed at a great speed.
When electrons and holes are injected into the electron and hole transport layers from the cathode and the anode, respectively, the electrons and the holes migrate to the light emitting layer through the electron and hole transport layers, respectively, and meet in the light emitting layer to form excitons and excite light emitting molecules, and redundant energy can be released in the form of light quanta.
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 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 considered as a next-generation color display device.
The process of fabricating an organic Electroluminescent (EL) device is described as follows:
(1) the 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) is 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 of 4, 4' -bis [ N- (1-naphthyl) -N-phenylamino ] biphenyl (NPB), and the hole layer is formed to a thickness of 30 to 60 nanometers (nm) by a general evaporation and coating method.
(4) Thereafter, an organic light emitting layer is formed. If doping is required, a dopant may be added. In the case of light emission, the organic light emitting layer is generally evaporated to a thickness of 30 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 an electron injection and transport layer is formed on the organic light emitting layer and then evaporated.
(6) And finally coating a cathode layer and coating a protective layer on the cathode.
Light emitting devices emitting (or displaying) blue, green, and red colors are fabricated according to the method of forming the light emitting layer in the above structure. As the light emitting material, excitons are formed by recombination of electrons and holes injected from each electrode. Singlet excitons emit fluorescence, triplet excitons emit phosphorescence. Singlet excitons that emit fluorescence have a 25% formation probability, whereas triplet excitons that emit phosphorescence have a 75% formation probability. Thus, the triplet excitons provide greater luminous efficiency than the singlet excitons. Such organic materials can have a 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 as color purity increases, visibility is reduced, and it is difficult to provide high luminous efficiency. Accordingly, there is a need to develop an organic material that can 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, which substantially obviate one or more problems due to limitations and disadvantages of the related art.
It is another object of the present invention to provide an organic electroluminescent device having high color purity, high luminance and long durability by applying the 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):
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 is1To R10Independently 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)11R12)、NR11、Si(R11R12)；
R11And R12Selected from substituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;
X1—X9selected from carbon or nitrogen.
Further, said LAThe group is selected from one of the following structural formulas:
further, said LBThe group is selected from one of the following structural formulas:
preferably, the organic compound of the present invention is selected from the group of organic compounds of the following structures:
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 of a hole injection layer, a hole transport layer, a luminescent layer, a hole blocking layer, an electron injection layer and an electron transport layer, and is characterized in that: at least one organic compound layer contains at least one organic compound according to the present invention.
An organic compound of the present invention is used as a dopant in a light-emitting layer of an organic electroluminescent device.
The organic electroluminescent device of the present invention may be applied to an Organic Light Emitting Device (OLED), an Organic Solar Cell (OSC), electronic Paper (e-Paper), an Organic Photoreceptor (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, there is shown in the drawings,
fig. 1 illustrates a graph showing a decrease in visibility as the color purity of an organic electroluminescent device increases (i.e., as the X value of chromaticity coordinates becomes larger).
FIG. 2 illustrates the structural formulae of compounds 2-TNATA, NPB, Ir (ppy)3, GH-1, GH-2 and Alq3 used in embodiments of the present 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 following describes a method of forming the organic compound according to the present invention.
Example 1: synthesis of C-1
1. Synthesis of intermediate L-1:
step 1A 500mL reaction flask was charged with intermediate L-1-4(10.0g,30.7mmol), L-1-5(5.1g,30.7mmol), tetrakis (triphenylphosphine) palladium (5 mol%), K2CO3(17.0g,122.8mmol),1, 4-dioxane (200mL) and water (50 mL). The reaction system is heated to 80 ℃ and reacts for 12 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and the crude product obtained by recrystallization was passed through a silica gel column to obtain intermediate L-1-3(5.2g, yield 70%). Mass spectrum m/z: theoretical value: 242.27, respectively; measured value: 242.07.
step 2A 1-L round-bottom flask was charged with L-1-3(4.6g,19.1mmol), and 180mL of dichloromethane, and stirred at room temperature. Bromine (3.4mL,66mmol) was diluted and added dropwise to 50mL of methylene chloride, and the mixture was stirred at room temperature for 8 hours, and after completion of the reaction, 100mL of acetone was added to the reaction vessel and stirred. The resulting solid was filtered and washed with acetone. The solid was recrystallized from monochlorobenzene to yield intermediate L-1-2(5.8g, 76%). Mass spectrum m/z: theoretical value: 400.06, respectively; measured value: 397.89.
step 3L-1-2 (4.0g,10mmol), tetrahydrofuran (180mL) were added to a 1L round bottom flask under nitrogen and stirred at ambient temperature. N-butyllithium (4.4mL,11mmol) was slowly added dropwise at-78 deg.C, methyl bromide-D3 (1.4g, 11mmol) was added dropwise half an hour later, and the mixture was stirred for 2 hours, further stirred at room temperature for 4 hours, and then water was added thereto to stop the reaction. Extracted with dichloromethane and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and the crude product obtained by recrystallization was passed through a silica gel column to obtain intermediate L-1-1(3.0g, 89%). Mass spectrum m/z: theoretical value: 338.21, respectively; measured value: 337.02.
step 4A 500mL reaction flask was charged with L-1-1(14.1g,41.8mmol), A (12.0g,41.8mmol), potassium carbonate (11.7g,104.6mmol), palladium tetrakistriphenylphosphine (2.4g,2.1mmol),1, 4-dioxane (140mL) and water (70 mL). The reaction system is heated to 60 ℃ and reacts 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(10.3g, yield 60%). Mass spectrum m/z: theoretical value: 408.55, respectively; measured value: 408.22.
synthesis of C-1 dichloro-crosslinked dimer Complex
A mixed solution of iridium trichloride monohydrate (3g, 10mmol), ligand L-2(4.3g, 22.1mmol) and diethanolamoether in a ratio of 3:1(120mL:40mL) to distilled water was charged into a dry two-necked round-bottomed flask, and heated under reflux for 24 hours, followed by addition of an appropriate amount of distilled water, filtration of the precipitated solid, and washing of the solid with methanol and petroleum ether to obtain C-1 dichloro-crosslinked dimer complex (3.7g, yield: 61%). Mass spectrum m/z: theoretical value: 1218.03, respectively; measured value: 1218.65. the above results confirmed that the obtained product was the objective product.
3. Synthesis of intermediate I-1
In a round bottom flask, dichloro-crosslinked dimer complex (3.4g, 2.8mmol) was dissolved in 200mL of dichloromethane. In a separate flask, silver (I) triflate (1.6g, 6.1mmol) was dissolved in 100mL of MeOH. It was added slowly to the dimer solution at room temperature with constant stirring. The reaction was stirred overnight in the dark and then filtered through celite to remove the silver chloride precipitate. The solvent was removed under reduced pressure to give intermediate I-1(4.0g, yield: 91%) which was used without further purification. Mass spectrum m/z: theoretical value: 785.71, respectively; measured value: 786.33. the above results confirmed that the obtained product was the objective product.
Synthesis of C-1
Intermediate I-1(4.3g, 5.5mmol) and ligand L-1(6.8g, 16.6mmol) were dissolved in a mixed solvent of DMF (100mL) and 2-ethoxyethanol (100mL) and heated at 130 ℃ for 18 hours. After the solvent was evaporated, the crude product was purified by column chromatography using 65 to 100% dichloromethane-containing hexane eluent to give C-1(2.4g, yield: 45%). Mass spectrum m/z: theoretical value: 980.09, respectively; measured value: 980.27.
example 2:
example 2: synthesis of C-15
1. Synthesis of intermediate L-2:
step 1A 500mL reaction flask was charged with intermediate L-15-5(11.1g,30.7mmol), L-15-6(5.1g,30.7mmol), tetrakis (triphenylphosphine) palladium (5 mol%), K2CO3(17.0g,122.8mmol),1, 4-dioxane (200mL) and water (50 mL). The reaction system is heated to 80 ℃ and reacts for 12 hours under the protection of nitrogen. After completion of the reaction, the reaction solution was cooled to room temperature and extracted with o-dichlorobenzene and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and the crude product obtained by recrystallization was passed through a silica gel column to obtain intermediate L-15-4(5.8g, yield 68%). Mass spectrum m/z: theoretical value: 276.72, respectively; measured value: 276.03.
step 2A 500mL reaction flask was charged with L-15-4(11.6g,41.8mmol), L-15-3(9.2g,41.8mmol), potassium carbonate (11.7g,104.6mmol), palladium tetrakistriphenylphosphine (2.4g,2.1mmol),1, 4-dioxane (140mL) and water (70 mL). The reaction system is heated to 60 ℃ and reacts 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(7.7g, yield 55%). Mass spectrum m/z: theoretical value: 333.38, respectively; measured value: 333.12.
step 3A 1-L round-bottom flask was charged with L-1-2(6.4g,19.1mmol), and 180mL of dichloromethane, and stirred at room temperature. Bromine (0.8mL,16mmol) was diluted and added dropwise to 50mL of methylene chloride, and the mixture was stirred at room temperature for 8 hours, and after completion of the reaction, 100mL of acetone was added to the reaction vessel and stirred. The resulting solid was filtered and washed with acetone. The solid was recrystallized from monochlorobenzene to yield intermediate L-1-1(5.3g, 68%). Mass spectrum m/z: theoretical value: 412.28, respectively; measured value: 411.03.
step 4. A1L round-bottom flask was charged with L-1-1(4.1g,10mmol), tetrahydrofuran (180mL) under nitrogen and stirred at ambient temperature. N-butyllithium (4.4mL,11mmol) was slowly added dropwise at-78 deg.C, methyl bromide-D3 (1.4g, 11mmol) was added dropwise half an hour later, and the mixture was stirred for 2 hours, further stirred at room temperature for 4 hours, and then water was added thereto to stop the reaction. Extracted with dichloromethane and water. The organic layer was dried over anhydrous magnesium sulfate, concentrated, and the crude product obtained by recrystallization was passed through a silica gel column to obtain intermediate L-1(3.0g, 85%). Mass spectrum m/z: theoretical value: 350.43, respectively; measured value: 350.15.
synthesis of C-15
Intermediate I-1(4.3g, 5.5mmol) and ligand L-15(5.8g, 16.6mmol) were dissolved in a mixed solvent of DMF (100mL) and 2-ethoxyethanol (100mL) and heated at 130 ℃ for 18 hours. After the solvent was evaporated, the crude product was purified by column chromatography using 65-100% dichloromethane in hexane as an eluent to obtain C-15(2.4g, yield: 47%). Mass spectrum m/z: theoretical value: 921.97, respectively; measured value: 922.20.
example 3: preparation of Compound 22
Compound 22 was obtained according to the synthesis method of example 1. Mass spectrum m/z, theoretical value: 1158.24, respectively; measured value: 1158.28.
example 4: preparation of Compound 108
Compound 108 was obtained according to the synthesis method of example 1. Mass spectrum m/z, theoretical value: 907.15, respectively; measured value: 907.33.
example 5: preparation of Compound 119
Compound 119 was obtained according to the synthesis method described in example 1. Mass spectrum m/z, theoretical value: 1056.23, respectively; measured value: 1056.25.
example 6: preparation of Compound 134
Compound 134 was obtained according to the synthesis method of example 1. Mass spectrum m/z, theoretical value: 972.17, respectively; measured value: 972.34.
device example 1
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. Then, the patterned ITO glass substrate was washed. The substrate is then placed in a vacuum chamber. The standard pressure was set to 1X 10-6And (4) supporting. Thereafter, 2-TNATA is coated on the ITO substrate
NPB
(GH1+GH2)+C-1(8％)
BCP
Alq3 
LiF
And Al
The sequence of (a) and (b) forming layers of organic material.
Device example 2
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. Then, the patterned ITO glass substrate was washed. The substrate is then placed in a vacuum chamber. The standard pressure was set to 1X 10-6And (4) supporting. Thereafter, 2-TNATA is coated on the ITO substrate
NPB
(GH1+GH2)+C-15(8％)
BCP
Alq3 
LiF
And Al
The sequence of (a) and (b) forming layers of organic material.
Device example 3
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. Then, the patterned ITO glass substrate was washed. The substrate is then placed in a vacuum chamber. The standard pressure was set to 1X 10-6And (4) supporting. Thereafter, 2-TNATA is coated on the ITO substrate
NPB
(GH1+GH2)+C-22(8％)
BCP
Alq3 
LiF
And Al
The sequence of (a) and (b) forming layers of organic material.
Device example 4
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. Then, the patterned ITO glass substrate was washed. The substrate is then placed in a vacuum chamber. The standard pressure was set to 1X 10-6And (4) supporting. Thereafter, 2-TNATA is coated on the ITO substrate
NPB
(GH1+GH2)+C-108(8％)
BCP
Alq3 
LiF
And Al
The sequence of (a) and (b) forming layers of organic material.
Device example 5
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. Then, the patterned ITO glass is washedA substrate. The substrate is then placed in a vacuum chamber. The standard pressure was set to 1X 10-6And (4) supporting. Thereafter, 2-TNATA is coated on the ITO substrate
NPB
(GH1+GH2)+C-119(8％)
BCP
Alq3 
LiF
And Al
The sequence of (a) and (b) forming layers of organic material.
Device example 6
The ITO glass substrate was patterned to have a light-emitting area of 3mm × 3 mm. Then, the patterned ITO glass substrate was washed. The substrate is then placed in a vacuum chamber. The standard pressure was set to 1X 10-6And (4) supporting. Thereafter, 2-TNATA is coated on the ITO substrate
NPB
(GH1+GH2)+C-134(8％)
BCP
Alq3 
LiF
And Al
The sequence of (a) and (b) 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 area of 3mm × 3 mm. Then, the patterned ITO glass substrate was washed. The substrate is then placed in a vacuum chamber. The standard pressure was set to 1X 10-6And (4) supporting. 2-TNATA on an ITO substrate
NPB
(GH1+GH2)+Ir(ppy)3(8％)
BCP
Alq3 
LiF
And Al
The sequence of (a) and (b) forming layers of organic material.
The characteristics of voltage and 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 at high efficiency at low voltage even when the color purity is high. Also, the current efficiency of example 2 increased by 20% or more compared to the comparative example.
It will be apparent to those skilled in the art that many modifications and variations can be made in the present invention without departing from the spirit and scope of the invention. It is therefore contemplated that the present invention cover the modifications and variations of this invention provided they come 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 the compound represented by formula (I) as a light emitting layer of the organic electroluminescent device.
Claims (7)
1. An organic compound represented by the following formula (I):
wherein R is1To R10Independently 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)11R12)、NR11、Si(R11R12)；
R11And R12Is selected from the group consisting ofSubstituted or unsubstituted C1-C15 alkyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C2-C30 heteroaryl;
X1—X9selected from carbon or nitrogen.
2. An organic compound according to claim 1, characterized in that: the organic compound is shown in the structural formula (I) in the specification, wherein L isAThe moiety is a structure formed by a formula selected from the group consisting of:
3. an organic compound according to claim 1, characterized in that: the organic compound is shown in the structural formula (I) in the specification, wherein L isBThe moiety is a structure formed by a formula selected from the group consisting of:
4. an organic compound according to claim 1, characterized in that: the organic compound is selected from compounds formed by the following structural formula:
5. an organic electroluminescent device comprising a cathode layer, an anode layer and an organic layer, the organic layer comprising at least one of a hole injection layer, a hole transport layer, a light emitting layer, a hole blocking layer, an electron injection layer, an electron transport layer, characterized in that: at least one organic compound layer comprising at least one organic compound as claimed in claim 1 to 4.
6. The organic electroluminescent device according to claim 5, wherein the organic compound according to any one of claims 1 to 4 is used as a dopant in a light-emitting layer of the device.
7. Use of the organic electroluminescent device according to claim 5 in an Organic Light Emitting Device (OLED), an Organic Solar Cell (OSC), electronic Paper (e-Paper), an Organic Photoreceptor (OPC), or an Organic Thin Film Transistor (OTFT).
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| CN113480576A (en) * | 2021-07-07 | 2021-10-08 | 北京八亿时空液晶科技股份有限公司 | Metal complex, organic electroluminescent element and consumer product |
| US20220102652A1 (en) * | 2020-09-29 | 2022-03-31 | Samsung Electronics Co., Ltd. | Organometallic compound, organic light-emitting device including the same, and electronic apparatus including the organic light-emitting device |
| EP4016656A1 (en) * | 2020-12-16 | 2022-06-22 | Samsung Electronics Co., Ltd. | Organometallic compound, organic light-emitting device including the same, and diagnostic composition including the organometallic compound |
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| US20220102652A1 (en) * | 2020-09-29 | 2022-03-31 | Samsung Electronics Co., Ltd. | Organometallic compound, organic light-emitting device including the same, and electronic apparatus including the organic light-emitting device |
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| CN113480576A (en) * | 2021-07-07 | 2021-10-08 | 北京八亿时空液晶科技股份有限公司 | Metal complex, organic electroluminescent element and consumer product |
| CN114874268A (en) * | 2022-04-28 | 2022-08-09 | 北京八亿时空液晶科技股份有限公司 | Organic electroluminescent material, organic electroluminescent element and consumer product |
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