CN110590851A - Red phosphorescent compound and organic electroluminescent device using the same - Google Patents
Red phosphorescent compound and organic electroluminescent device using the same Download PDFInfo
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- CN110590851A CN110590851A CN201910808062.8A CN201910808062A CN110590851A CN 110590851 A CN110590851 A CN 110590851A CN 201910808062 A CN201910808062 A CN 201910808062A CN 110590851 A CN110590851 A CN 110590851A
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- organic electroluminescent
- electroluminescent device
- red phosphorescent
- phosphorescent compound
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- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
- 230000005525 hole transport Effects 0.000 claims abstract description 4
- -1 methylquinolyl Chemical group 0.000 claims description 8
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
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- 229910052751 metal Inorganic materials 0.000 claims description 3
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004431 deuterium atom Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
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- 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
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- BKIHFZLJJUNKMZ-UHFFFAOYSA-N 1-(3,5-dimethylphenyl)ethanone Chemical compound CC(=O)C1=CC(C)=CC(C)=C1 BKIHFZLJJUNKMZ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- WIWBLJMBLGWSIN-UHFFFAOYSA-L dichlorotris(triphenylphosphine)ruthenium(ii) Chemical compound [Cl-].[Cl-].[Ru+2].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 WIWBLJMBLGWSIN-UHFFFAOYSA-L 0.000 description 2
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
- CLKBZWDZDVOIGJ-UHFFFAOYSA-N (2-amino-5-chlorophenyl)methanol Chemical compound NC1=CC=C(Cl)C=C1CO CLKBZWDZDVOIGJ-UHFFFAOYSA-N 0.000 description 1
- DJGHSJBYKIQHIK-UHFFFAOYSA-N (3,5-dimethylphenyl)boronic acid Chemical compound CC1=CC(C)=CC(B(O)O)=C1 DJGHSJBYKIQHIK-UHFFFAOYSA-N 0.000 description 1
- SZCPTRGBOVXVCA-UHFFFAOYSA-N 2-amino-6-chlorobenzoic acid Chemical compound NC1=CC=CC(Cl)=C1C(O)=O SZCPTRGBOVXVCA-UHFFFAOYSA-N 0.000 description 1
- XHYVBIXKORFHFM-UHFFFAOYSA-N 2-amino-6-methylbenzoic acid Chemical compound CC1=CC=CC(N)=C1C(O)=O XHYVBIXKORFHFM-UHFFFAOYSA-N 0.000 description 1
- OFUFXTHGZWIDDB-UHFFFAOYSA-N 2-chloroquinoline Chemical compound C1=CC=CC2=NC(Cl)=CC=C21 OFUFXTHGZWIDDB-UHFFFAOYSA-N 0.000 description 1
- ZAZPDOYUCVFPOI-UHFFFAOYSA-N 2-methylpropylboronic acid Chemical compound CC(C)CB(O)O ZAZPDOYUCVFPOI-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910021380 Manganese Chloride Inorganic materials 0.000 description 1
- GLFNIEUTAYBVOC-UHFFFAOYSA-L Manganese chloride Chemical compound Cl[Mn]Cl GLFNIEUTAYBVOC-UHFFFAOYSA-L 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
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- 239000012043 crude product Substances 0.000 description 1
- 238000005516 engineering process Methods 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
- 239000012535 impurity Substances 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- IUYHWZFSGMZEOG-UHFFFAOYSA-M isopropylmagnesium chloride Substances [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 1
- 239000011565 manganese chloride Substances 0.000 description 1
- 235000002867 manganese chloride Nutrition 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
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 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
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- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- RMNIZOOYFMNEJJ-UHFFFAOYSA-K tripotassium;phosphate;hydrate Chemical compound O.[K+].[K+].[K+].[O-]P([O-])([O-])=O RMNIZOOYFMNEJJ-UHFFFAOYSA-K 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
-
- 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
-
- 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
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
-
- 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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- 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
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- 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
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present invention discloses a red phosphorescent compound and an organic electroluminescent device using the same, in the organic electroluminescent device including 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 deposited in sequence with each other, the organic electroluminescent device may use a phosphorescent compound represented by the following formula I as a dopant of the light emitting layer:wherein R1, R2, R3, R4, R5 and R6 are independently selected from one of H, C1-C6 alkyl and C5-C8 cycloalkyl. The red phosphorescent material has high efficiency, high color purity and narrow spectrum effectAnd (5) fruit.
Description
Technical Field
The present invention relates to an organic electroluminescent device, and more particularly, to a red phosphorescent compound and an organic electroluminescent device using the same. In particular, the present invention relates to a red phosphor used as a dopant of a light emitting layer of an organic electroluminescent device.
Background
In recent years, as the size of display devices is getting larger, flat display devices occupying less space are more and more required. 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 developing at a great speed, and many prototypes have been disclosed.
When electric charges are injected into an organic layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode), the organic electroluminescent device emits light. More specifically, when an electron and a hole form a pair, light is emitted, and the newly generated electron-hole pair decays. 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, since the organic electroluminescent device can reproduce pictures using three colors (i.e., green, blue, and red), the organic electroluminescent device is widely recognized as a next-generation color display device that can reproduce clear images.
The process of fabricating an organic light emitting diode (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 deposited on the anode material. The hole injection layer is formed of a copper phthalocyanine (CuPc) layer having a thickness of 10 nanometers (nm) to 30 nm.
(3) A void-transporting layer (HTL) is then deposited. The hole transport layer is mainly formed of 4, 4' -bis [ N- (1-naphthyl) -N-phenylamino ] biphenyl (NPB), which is first treated with vacuum evaporation and then coated to have a thickness of 30 nanometers (nm) to 60 nanometers (nm).
(4) Thereafter, an organic light emitting layer is formed. At this time, a dopant may be added, if necessary. In the case of green light emission, the organic light emitting layer is generally formed of tris (8-hydroxyquinolinato) aluminum (Alq3) evaporated in vacuum to have a thickness of 30 to 60 nanometers (nm). And, MQD (N-methyl quinacridone copper) is used as a dopant (or impurity).
(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/transport layer is formed on the organic light emitting layer. In the case of green light emission, Alq3 of step (4) has excellent electron transport ability. Therefore, electron injection and transport layers are not necessarily required.
(6) Finally, a cathode layer is coated, and a protective layer is coated on the whole structure.
Light emitting devices that emit (or display) blue, green, and red colors, respectively, are determined 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 and 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, triplet excitons provide greater luminous efficiency than singlet excitons. In such a phosphorescent material, the red phosphorescent material may have greater luminous efficiency than the fluorescent material. Therefore, as an important factor for improving the efficiency of the organic electroluminescent device, red phosphorescent materials are being widely studied.
When such a phosphorescent material is used, high luminous efficiency, high color purity and prolonged durability are required. Most particularly, when a red phosphorescent material is used, visibility is reduced as color purity increases (i.e., the X value of CIE chromaticity coordinates becomes larger), thereby causing difficulty in providing high luminous efficiency. Accordingly, there is a need to develop a red phosphorescent material that can provide excellent chromaticity coordinates (CIE color purity of X is 0.63 or more), improved luminous efficiency, and extended durability.
Disclosure of Invention
An object of the present invention devised to solve the problem lies on providing a red phosphorescent compound and an organic electroluminescent device using the same that substantially obviate one or more problems due to limitations and disadvantages of the related art.
Another object of the present invention devised to solve the problem lies on providing an organic electroluminescent device having high color purity, high luminance and long durability by incorporating the compound represented by formula (i) into a light-emitting layer of the organic electroluminescent device as a dopant.
The object of the present invention can be achieved by providing a red phosphorescent compound represented by the following formula (I).
A red phosphorescent compound represented by the following formula (I):
wherein R1, R2, R3, R4, R5 and R6 are independently selected from one of H, C1-C6 alkyl and C5-C8 cycloalkyl.
Further, the C1-C6 alkyl or C5-C8 cycloalkyl is selected from one of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, n-pentyl, cyclopentyl and cyclohexyl.
Further, the hydrogen atoms of the C1-C6 alkyl groups or the C5-C8 cycloalkyl groups are all replaced by deuterium atoms.
Further, the La group is selected from one of the following structural formulas:
further, the red phosphorescent compound, wherein the formula (i) is any one of the following structural formulae:
in another aspect of the present invention, there is provided an organic electroluminescent device comprising 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, which are sequentially deposited one on another, wherein the organic electroluminescent device may use any one of the above-described phosphorescent compounds as a dopant of the light emitting layer.
Any one of Al and Zn metal complexes and carbazole derivatives may be used as a host material of the light emitting layer, and the amount of the dopant may be in the range of 0.1 to 50% by weight. When the amount of the dopant used is within the above range, the efficiency of the present invention can be improved. And the ligand of each of the Al and Zn metal complexes may include quinolyl, biphenyl, isoquinolyl, phenyl, methylquinolyl, dimethylquinolyl, dimethylisoquinolyl, wherein the carbazole derivative may include CBP.
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 the compounds copper (II) phthalocyanine (CuPc), NPB, (btp)2Ir (acac), Alq3 and BALq 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 method of forming the red phosphorescent compound according to the present invention is described below.
Examples of formation
1. Synthesis of intermediate Sub-1
To a three-necked flask, 2-chloroquinoline (10.0g,61.1mmol),3, 5-dimethylbenzeneboronic acid (11.0g,73.3mmol), and 2M-potassium carbonate (120mL) were dissolved in tetrahydrofuran (120mL) under nitrogen. The nitrogen was purged for 30 minutes, and palladium tetrakistriphenylphosphine (5 mol%) as a catalyst was added. The reaction was warmed to 80 ℃ and stirred under reflux for 12 hours. After cooling to room temperature, the reaction mixture was quenched with water, and the reaction mixture was extracted with ethyl acetate and saturated brine. The mixture was washed with saturated brine two to three times, and the organic phase was taken out. The organic phase was dried over anhydrous magnesium sulfate and concentrated. The intermediate Sub-1(10.0g, yield 70%) was obtained by separation and purification on a silica gel column.
LC-MS:M/Z 234.3(M+H)+
2. Synthesis of intermediate Sub-2
To a mixture of lithium aluminum hydride (4.5g,119.0mmol) and dry tetrahydrofuran (100mL) was added dropwise a solution of 2-amino-6-methylbenzoic acid (15.0g,99.2mmol) and dry tetrahydrofuran (50mL) under nitrogen protection, and after completion of the addition, the mixture was stirred at room temperature for 2 hours, quenched with 10mL of water, and then a solution of sodium hydroxide (5g) and water (50mL) was added. Filtering, extracting the filtrate with ethyl acetate, combining the organic phases, drying with anhydrous sodium sulfate, filtering, and concentrating under reduced pressure. The concentrate was crystallized from ethyl acetate/petroleum ether to give intermediate Sub-2(11.6g, yield 85%)). LC-MS M/Z138.2 (M + H) +)+
3. Synthesis of intermediate Sub-3
2-amino-5-chlorobenzyl alcohol (10.0g,72.9mmol),3, 5-dimethylacetophenone (16.2g,109.3mmol), tris (triphenylphosphine) ruthenium (II) dichloride (2 mol%), potassium hydroxide (4.5g,80.2mmol) and toluene (100mL) were added to a reaction flask, heated and stirred to reflux, and water was separated by a condensate reflux trap. When the reaction was complete, cool to room temperature and filter through silica gel pad. The product was further purified by column chromatography (eluent: n-hexane/ethyl acetate 2/100) and finally concentrated by isopropylCrystallization of the alcohol gave intermediate Sub-3(10.5g, 58% yield). LC-MS M/Z248.3 (M + H)+
4. Synthesis of intermediate Sub-4
To a mixture of lithium aluminum hydride (10.6g,279.8mmol) and dry tetrahydrofuran (250mL) was added dropwise a solution of 2-amino-6-chlorobenzoic acid (40.0g,233.1mmol) and dry tetrahydrofuran (300mL) under nitrogen protection, and after completion of the addition, the mixture was stirred at room temperature for 2 hours, quenched with 15mL of water, and then a solution of sodium hydroxide (10g) and water (100mL) was added. Filtering, extracting the filtrate with ethyl acetate, combining the organic phases, drying with anhydrous sodium sulfate, filtering, and concentrating under reduced pressure. The concentrate was crystallized from ethyl acetate/petroleum ether to give intermediate Sub-4(31.2g, yield 85%)). LC-MS M/Z158.6 (M + H)+
5. Synthesis of intermediate Sub-5
The intermediate Sub-4(30.0g,190.4mmol),3, 5-dimethylacetophenone (56.4g,380.7mmol), tris (triphenylphosphine) ruthenium (II) dichloride (2 mol%), potassium hydroxide (11.7g,209.4mmol) and toluene (350mL) were added to a reaction flask, heated to reflux, and water was removed via a condensate reflux trap. When the reaction was complete, cool to room temperature and filter through silica gel pad. The product was further purified by column chromatography (eluent: n-hexane/ethyl acetate 2/100) and finally crystallized from isopropanol to give intermediate Sub-5(28.0g, yield 55%). LC-MS M/Z268.8(M + H)+
6. Synthesis of intermediate Sub-6
Intermediate Sub-5(15.0g,56.0mmol), MnCl2(1 mol%) and THF (180mL) were added under argon protection to a two-necked round bottom flask. After cooling to 0 deg.C, 2M-isopropylmagnesium chloride (42.0mL, 84) was added slowly via syringe.0 mmol). After stirring at 0 ℃ for 4 hours, the reaction mixture was quenched with saturated ammonium chloride solution (100mL) and water (150 mL). Extracted with EtOAc and dried over anhydrous magnesium sulfate. After removal of the solvent in vacuo, the crude product was purified by column (n-hexane: EtOAc ═ 50:1) to give intermediate Sub-6(10.0g, yield 65%). LC-MS M/Z276.4 (M + H)+
7. Synthesis of intermediate Sub-7
Intermediate Sub-5(10.0g,37.3mmol), isobutylboronic acid (7.6g,74.7mmol), tris (dibenzylideneacetone) dipalladium (2 mol%), 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (4 mol%), potassium phosphate (monohydrate) (31.7g,149.4mmol), toluene (150mL), nitrogen substitution, and leaving under nitrogen protection to heat reflux for 18 hours. The reaction was cooled to room temperature and purified by column chromatography using n-hexane/ethyl acetate 100/2 as eluent to give intermediate Sub-7(9.3g, yield 86%).
LC-MS:M/Z 290.4(M+H)+
8. Synthesis of dichloro-crosslinked dimer complexes
A mixed solution of iridium trichloride monohydrate (4.0g,13.4mmol), intermediate Sub-1(6.9g,29.5mmol) and diethanol monoethyl ether at a ratio of 3/1(120mL/40mL) to distilled water was charged into a dry two-necked round-bottomed flask, heated under reflux for 24 hours, followed by addition of an appropriate amount of distilled water, and the precipitated solid was filtered and washed with methanol and petroleum ether to give a dichloro-crosslinked dimer complex (5.7g, yield 62%). LC-MS M/Z1385.5 (M + H)+
Synthesis of RD-004
Dichloro-crosslinked dimer complex (3.0g,2.2mmol),3, 7-diethyl-3, 7-dimethyl-4, 6-dione (D1.6g,6.5mmol), anhydrous sodium carbonate (1.1g,10.8mmol) and 80ml of 2-ethoxyethanol were added to a two-necked round-bottomed flask, followed by heating under reflux for 6 hours, stopping heating, cooling to room temperature, adding an appropriate amount of distilled water, and filtering off a solid. The solid was dissolved in dichloromethane and passed through a short column of silica gel. The solvent was removed under reduced pressure and the resulting solid was concentrated and washed with methanol followed by petroleum ether to give RD-004(2.5g, 65% yield) the desired product. LC-MS M/Z897.2 (M + H)+
10. Synthesis of dichloro-crosslinked dimer complexes
A mixed solution of iridium trichloride monohydrate (4.0g,13.4mmol), intermediate Sub-3(7.3g,29.5mmol) and diethanol monoethyl ether at a ratio of 3/1(120mL/40mL) to distilled water was charged into a dry two-necked round-bottomed flask, heated under reflux for 24 hours, followed by addition of an appropriate amount of distilled water, and the precipitated solid was filtered and washed with methanol and petroleum ether to give a dichloro-crosslinked dimer complex (5.9g, yield 61%). LC-MS M/Z1441.7 (M + H)+
Synthesis of RD-029
Dichloro-crosslinked dimer complex (3.0g,2.1mmol),3, 7-diethyl-3, 7-dimethyl-4, 6-dione (1.5g,6.2mmol), anhydrous sodium carbonate (1.1g,10.4mmol) and 80ml of 2-ethoxyethanol were added to a two-necked round-bottomed flask, and then heated under reflux for 6 hours, the heating was stopped, cooled to room temperature, an appropriate amount of distilled water was added, and a solid was filtered off. The solid was dissolved in dichloromethane and passed through a short column of silica gel. The solvent was removed under reduced pressure and the resulting solid was concentrated and washed with methanol followed by petroleum ether to give RD-029(2.3g, 59% yield) as the desired product. LC-MS M/Z925.2 (M + H)+
12. Synthesis of dichloro-crosslinked dimer complexes
A mixed solution of iridium trichloride monohydrate (4.0g,13.4mmol), intermediate Sub-6(8.1g,29.5mmol) and diethanol monoethyl ether at a ratio of 3/1(120mL/40mL) to distilled water was charged into a dry two-necked round-bottomed flask, heated under reflux for 24 hours, followed by addition of an appropriate amount of distilled water, and the precipitated solid was filtered and washed with methanol and petroleum ether to give a dichloro-crosslinked dimer complex (6.0g, yield 58%). LC-MS M/Z1553.9 (M + H)+
Synthesis of RD-072
Dichloro-crosslinked dimer complex (3g,1.9mmol),3, 7-diethyl-3, 7-dimethyl-4, 6-dione (1.4g,5.8mmol), anhydrous sodium carbonate (1.0g,9.7mmol) and 80ml of 2-ethoxyethanol were added to a two-necked round-bottomed flask, and then heated under reflux for 6 hours, the heating was stopped, the temperature was lowered to room temperature, an appropriate amount of distilled water was added, and a solid was filtered off. The solid was dissolved in dichloromethane and passed through a short column of silica gel. The solvent was removed under reduced pressure and the resulting solid was concentrated and washed with methanol followed by petroleum ether to give RD-072(2.1g, 56% yield) the desired product. LC-MS M/Z981.4 (M + H)+
14. Synthesis of dichloro-crosslinked dimer complexes
A mixed solution of iridium trichloride monohydrate (4g,13.4mmol), intermediate Sub-7(8.5g,29.5mmol) and diethanol monoethyl ether at 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, and the precipitated solid was filtered and washed with methanol and petroleum ether to obtain dichloro-crosslinked dimer complex (6.0g, yield 56%). LC-MS M/Z1610.0 (M + H)+
Synthesis of RD-098
Dichloro-crosslinked dimer complex (3g,1.9mmol),3, 7-diethyl-3, 7-dimethyl-4, 6-dione (1.3g,5.6mmol), anhydrous sodium carbonate (1.0g,9.3mmol) and 80ml of 2-ethoxyethanol were added to a two-necked round-bottomed flask, and then heated under reflux for 6 hours, the heating was stopped, the temperature was lowered to room temperature, an appropriate amount of distilled water was added, and a solid was filtered off. The solid was dissolved in dichloromethane and passed through a short column of silica gel. The solvent was removed under reduced pressure and the resulting solid was concentrated and washed with methanol followed by petroleum ether to give RD-098(2.1g, 55% yield) the desired product. LC-MS M/Z1009.4 (M + H)+
Examples of preferred embodiments are given below to describe the present invention. It should be clearly understood that the invention is not limited to the presented embodiments only.
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, CuPc was applied onto the ITO substrateNPBBAlq+RD-004(5％)Alq3LiFAnd AlThe sequence of (a) and (b) forming layers of organic material. At 0.9mA, the luminance is equal to 1030cd/m2(6.1V). In this case, CIEx is 0.667 and y is 0.331.
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, CuPc was applied onto the ITO substrateNPBBAlq+RD-029(5％)Alq3LiFAnd AlThe sequence of (a) and (b) forming layers of organic material. At 0.9mA, the luminance is equal to 1289cd/m2(6.2V). At this time, CIEx is equal to 0.664 and y is equal to 0.338.
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, CuPc was applied onto the ITO substrateNPBBAlq+RD-072(5％)Alq3LiFAnd AlThe sequence of (a) and (b) forming layers of organic material. At 0.9mA, the luminance is equal to 1232cd/m2(6.4V). In this case, CIEx is 0.662 and y is 0.340.
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, CuPc was applied onto the ITO substrateNPBBAlq+RD-098(5％)Alq3LiFAnd AlThe sequence of (a) and (b) forming layers of organic material. At 0.9mA, the luminance is equal to 1321cd/m2(6.3V). In this case, CIEx is 0.662 and y is 0.339.
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. Thereafter, CuPc was applied onto the ITO substrateNPBBAlq+(btp)2Ir(acac)(5％)Alq3LiFAnd AlThe sequence of (a) and (b) forming layers of organic material. At 0.9mA, the luminance is equal to 780cd/m2(7.5V). In this case, CIEx is 0.659 and y is 0.329.
The characteristics of efficiency, chromaticity coordinates and luminance 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 the examples was increased by 40% or more compared to the comparative examples.
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 (8)
1. A red phosphorescent compound is characterized in that the structural formula is shown as a formula I,
wherein R1, R2, R3, R4, R5 and R6 are independently selected from one of H, C1-C6 alkyl and C5-C8 cycloalkyl.
2. The red phosphorescent compound of claim 1, wherein the C1-C6 alkyl group or the C5-C8 cycloalkyl group is one selected from the group consisting of a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a cyclopentyl group and a cyclohexyl group.
3. The red phosphorescent compound according to claim 2, wherein the hydrogen atoms of the C1 to C6 alkyl groups or C5 to C8 cycloalkyl groups are all replaced by deuterium atoms.
4. The red phosphorescent compound of claim 1, wherein the La group is selected from one of the following structural formulae:
5. the red phosphorescent compound of claim 1, wherein formula (i) is any one of the following structural formulae:
6. an organic electroluminescent device, characterized in that: the device comprises 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 which are sequentially deposited with each other; the organic electroluminescent device comprising a compound according to any of claims 1 to 5 as a dopant.
7. The organic electroluminescent device as claimed in claim 6, wherein any one of an Al or Zn metal complex and a carbazole derivative is used as a host material of the light emitting layer, and wherein the amount of the dopant used is in the range of 0.1 to 50% by weight.
8. The organic electroluminescent device as claimed in claim 6, wherein the ligand of each of the Al and Zn metal complexes includes quinolyl, biphenyl, isoquinolyl, phenyl, methylquinolyl, dimethylquinolyl, dimethylisoquinolyl, and wherein the carbazole derivative includes CBP.
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| CN109956977A (en) * | 2017-12-25 | 2019-07-02 | 北京夏禾科技有限公司 | The metal complex of the ligand containing heterocyclic substituted, and electroluminescent device and compound formulas comprising the complex compound |
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| CN101160369A (en) * | 2005-03-08 | 2008-04-09 | Lg电子株式会社 | Red phosphorescene compounds and organic electroluminescence devices using the same |
| US20120181511A1 (en) * | 2011-01-13 | 2012-07-19 | Universal Display Corporation | 5-Substituted 2 Phenylquinoline Complexes Materials for Light Emitting Diode |
| CN104277075A (en) * | 2013-07-01 | 2015-01-14 | 环球展览公司 | Ancillary ligands for organometallic complexes, device comprising the same, and formulation |
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