CN111116673A - 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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- CN111116673A CN111116673A CN201911372768.0A CN201911372768A CN111116673A CN 111116673 A CN111116673 A CN 111116673A CN 201911372768 A CN201911372768 A CN 201911372768A CN 111116673 A CN111116673 A CN 111116673A
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- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 15
- 238000002347 injection Methods 0.000 claims abstract description 13
- 239000007924 injection Substances 0.000 claims abstract description 13
- 239000002019 doping agent Substances 0.000 claims abstract description 10
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- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 4
- 230000005525 hole transport Effects 0.000 claims abstract description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 3
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims abstract description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 229910052799 carbon Inorganic materials 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
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- -1 methylquinolyl Chemical group 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 10
- 150000004696 coordination complex Chemical class 0.000 claims description 8
- 239000003446 ligand Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 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
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 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
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 150000001975 deuterium Chemical group 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
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- 230000015572 biosynthetic process Effects 0.000 description 21
- 238000003786 synthesis reaction Methods 0.000 description 19
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- 239000003208 petroleum Substances 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
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- 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 3
- SOQIDYYUSMPIDR-UHFFFAOYSA-N 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=CC=N1 SOQIDYYUSMPIDR-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
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- TYXNCWURLACYGB-UHFFFAOYSA-N 1,3-dicyclohexyl-2-methylpropane-1,3-dione Chemical compound C1CCCCC1C(=O)C(C)C(=O)C1CCCCC1 TYXNCWURLACYGB-UHFFFAOYSA-N 0.000 description 1
- GJMUCDMIIVSROW-UHFFFAOYSA-N 2,8-dimethylnonane-4,6-dione Chemical compound CC(C)CC(=O)CC(=O)CC(C)C GJMUCDMIIVSROW-UHFFFAOYSA-N 0.000 description 1
- CGLYWDKTFBMSHI-UHFFFAOYSA-N 2-chloro-1,7-naphthyridine Chemical compound C1=CN=CC2=NC(Cl)=CC=C21 CGLYWDKTFBMSHI-UHFFFAOYSA-N 0.000 description 1
- BMIBJCFFZPYJHF-UHFFFAOYSA-N 2-methoxy-5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound COC1=NC=C(C)C=C1B1OC(C)(C)C(C)(C)O1 BMIBJCFFZPYJHF-UHFFFAOYSA-N 0.000 description 1
- ONGBXISBKSVVFS-UHFFFAOYSA-N 2-methyl-1,3-diphenylpropane-1,3-dione Chemical compound C=1C=CC=CC=1C(=O)C(C)C(=O)C1=CC=CC=C1 ONGBXISBKSVVFS-UHFFFAOYSA-N 0.000 description 1
- YIWTXSVNRCWBAC-UHFFFAOYSA-N 3-phenylpentane-2,4-dione Chemical compound CC(=O)C(C(C)=O)C1=CC=CC=C1 YIWTXSVNRCWBAC-UHFFFAOYSA-N 0.000 description 1
- KKLCYBZPQDOFQK-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=CC=C1 KKLCYBZPQDOFQK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000004431 deuterium atom Chemical group 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
- 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
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- C07—ORGANIC CHEMISTRY
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- 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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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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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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Abstract
The present invention discloses a red phosphorescent compound and an organic electroluminescent device using the same, the 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 sequentially deposited one on another, the organic electroluminescent device using a phosphorescent compound represented by the following formula I as a dopant of the light emitting layer:
the compound is shown in the formula I, wherein A is independently selected from substituted or unsubstituted C6-C30 naphthyridine; r1、R2、R3、R4、R5And R6Independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstitutedOne of C5-C8 cycloalkyl and substituted or unsubstituted C6-C30 aryl; x1、X2、X3And X4Selected from C or N; n is selected from 1 or 2.
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 10nm 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 30nm to 60 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 30nm to 60 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 A is independently selected from substituted or unsubstituted C6-C30 naphthyridine;
R1、R2、R3、R4、R5and R6Independently selected from one of hydrogen, deuterium, halogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C5-C8 cycloalkyl and substituted or unsubstituted C6-C30 aryl; x1、X2、X3And X4Selected from C or N; n is selected from 1 or 2.
Further, the alkyl of C1-C6 or the cycloalkyl of C5-C8 is selected from one of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertiary butyl, n-pentyl, cyclopentyl and cyclohexyl.
Further, the hydrogen atoms of the alkyl groups of C1-C6 or the cycloalkyl groups of C5-C8 are all replaced by deuterium atoms.
Further, the La group is selected from one of the following structural formulas:
further, said LbThe 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:
the present invention also provides 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 can use any one of the above phosphorescent compounds as a dopant of the light emitting layer.
Any one of an Al metal complex, a Zn metal complex, and a carbazole derivative is used as a host material of the light-emitting layer, and the amount of the dopant is 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 metal complex and the Zn metal complex includes quinolyl, biphenyl, isoquinolyl, phenyl, methylquinolyl, dimethylquinolyl, dimethylisoquinolyl, wherein the carbazole derivative includes CBP.
Drawings
Fig. 1 shows a graph in which the visibility decreases as the color purity of the organic electroluminescent device increases (i.e., as the X value of the chromaticity coordinate becomes larger).
FIG. 2 shows the structural formulae of the compounds copper (II) phthalocyanine (CuPc), NPB, (btp)2Ir (acac), Alq3 and BALq used in the embodiment 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.
And (3) synthesis of an intermediate:
1. synthesis of intermediate L-1
Under nitrogen protection, 2-chloro-1, 7-naphthyridine (14.5g, 88.1mmol), 3, 5-deuterated-dimethylbromobenzeneboronic acid pinacol ester (23.1, 96.9mmol), and 2M-potassium carbonate (100mL) were added to a three-necked flask dissolved in tetrahydrofuran (100 mL). The nitrogen was purged for 30 minutes, and palladium tetrakistriphenylphosphine (3 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 ligand L-1(17.0g, yield: 80%) was obtained by separation and purification through a silica gel column. Mass spectrum m/z: theoretical value: 240.33, respectively; measured value: 240.95. the above results confirmed that the obtained product was the objective product.
2. Synthesis of intermediate L-2
To a three-necked flask, 2-chloro-4-phenyl-1, 7-naphthyridine (21.2g, 88.1mmol), pinacol phenylboronate (19.8, 96.9mmol), and 2M-potassium carbonate (100mL) were dissolved in tetrahydrofuran (100mL) under nitrogen. The nitrogen was purged for 30 minutes, and palladium tetrakistriphenylphosphine (3 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 ligand L-2 was isolated and purified by means of a silica gel column chromatography (19.9g, yield: 80%). Mass spectrum m/z: theoretical value: 282.34, respectively; measured value: 282.96. the above results confirmed that the obtained product was the objective product.
3. Synthesis of intermediate L-3
To a three-necked flask, 2-chloro-4-ethyl-1, 7-naphthyridine (14.8g, 88.1mmol), 3, 5-deuterated isopropylphenylboronic acid pinacol ester (29.3, 96.9mmol), and 2M-potassium carbonate (100mL) were dissolved in tetrahydrofuran (100mL) under nitrogen. The nitrogen was purged for 30 minutes, and palladium tetrakistriphenylphosphine (3 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 ligand L-3(23.4g, yield: 80%) was obtained by separation and purification through a silica gel column. Mass spectrum m/z: theoretical value: 332.54, respectively; measured value: 333.16. the above results confirmed that the obtained product was the objective product.
4. Synthesis of intermediate L-4
To a three-necked flask, 2-chloro-4-isopropyl-1, 7-naphthyridine (18.21g, 88.1mmol), 2-pyridineboronic acid pinacol ester (19.44, 96.9mmol), and 2M-potassium carbonate (100mL) were added dissolved in tetrahydrofuran (100mL) under nitrogen. The nitrogen was purged for 30 minutes, and palladium tetrakistriphenylphosphine (3 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 ligand L-4(17.57g, yield: 80%) was obtained by separation and purification through a silica gel column. Mass spectrum m/z: theoretical value: 249.31, respectively; measured value: 249.93. the above results confirmed that the obtained product was the objective product.
5. Synthesis of intermediate L-5
Under the protection of nitrogen, 8-bromo-4-isopropyl-1, 7-naphthyridine (22.12g, 88.1mmol), 3, 5-dimethyl-pinacol bromobenzeneboronic acid ester (22.5, 96.9mmol), and 2M-potassium carbonate (100mL) were added to a three-necked flask and dissolved in tetrahydrofuran (100 mL). The nitrogen was purged for 30 minutes, and palladium tetrakistriphenylphosphine (3 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 ligand L-5(19.5g, yield: 80%) was obtained by separation and purification through a silica gel column. Mass spectrum m/z: theoretical value: 276.38, respectively; measured value: 277.00. the above results confirmed that the obtained product was the objective product.
6. Synthesis of intermediate L-6
To a three-necked flask, 2-chloro-6-isopropyl-1, 7-naphthyridine (22.12g, 88.1mmol), 2-pyridineboronic acid pinacol ester (19.44, 96.9mmol), and 2M-potassium carbonate (100mL) were added dissolved in tetrahydrofuran (100mL) under nitrogen. The nitrogen was purged for 30 minutes, and palladium tetrakistriphenylphosphine (3 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 ligand L-6(17.57g, yield: 80%) was obtained by separation and purification through a silica gel column. Mass spectrum m/z: theoretical value: 249.32, respectively; measured value: 249.94. the above results confirmed that the obtained product was the objective product.
Example 1
Synthesis of C-109 dichloro-crosslinked dimer Complex
A mixed solution of iridium trichloride monohydrate (4.0g,13.4mmol), intermediate L-1(7.09g,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, filtration of the precipitated solid, and washing of the solid with methanol and petroleum ether to obtain C-109 dichloro crosslinked dimer complex (5.9g, yield 62%). Mass spectrum m/z: theoretical value: 1410.48, respectively; measured value: 1411.10. the above results confirmed that the obtained product was the objective product.
Synthesis of C-109
Dichloro-crosslinked dimer complex (3.1g,2.2mmol), pentane-2, 4-dione (0.65g,6.5mmol), anhydrous sodium carbonate (1.1g,10.8mmol) 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 C-109(2.2g, 65% yield) as the desired product. Mass spectrum m/z: theoretical value: 769.97, respectively; measured value: 770.59. the above results confirmed that the product was the target product.
Example 2
Synthesis of C-398 dichloro-crosslinked dimer Complex
A mixed solution of iridium trichloride monohydrate (4.0g,13.4mmol), intermediate L-2(8.3g,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, filtration of the precipitated solid, and washing of the solid with methanol and petroleum ether to obtain C-398 dichloro-crosslinked dimer complex (6.5g, yield 62%). Mass spectrum m/z: theoretical value: 1580.70, respectively; measured value: 1581.32. the above results confirmed that the obtained product was the objective product.
Synthesis of C-398
Dichloro-crosslinked dimer complex (3.5g,2.2mmol),2, 8-dimethyl-4, 6-nonanedione (1.2g,6.5mmol), anhydrous sodium carbonate (1.1g,10.8mmol) 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 C-398(2.7g, 65% yield) as the desired product. Mass spectrum m/z: theoretical value: 938.15, respectively; measured value: 938.77. the above results confirmed that the obtained product was the objective product.
Example 3
Synthesis of C-1053 dichloro-crosslinked dimer Complex
A mixed solution of iridium trichloride monohydrate (4.0g,13.4mmol), intermediate L-3(9.8g,29.5mmol) and diethanol monoethyl ether in a ratio of 3:1 to distilled water (120mL:40mL) 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 of C-1053 (7.4g, yield 62%). Mass spectrum m/z: theoretical value: 1783.49, respectively; measured value: 1784.11. the above results confirmed that the obtained product was the objective product.
Synthesis of C-1053
Dichloro-crosslinked dimer complex (3.9g,2.2mmol), 2-methyl-1, 3-diphenyl-1, 3-propane-dione (1.6g,6.5mmol), anhydrous sodium carbonate (1.1g,10.8mmol) 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 C-1053(3.1g, 65% yield) as the desired product. Mass spectrum m/z: theoretical value: 240.33, respectively; measured value: 240.90. the above results confirmed that the obtained product was the objective product.
Example 4
Synthesis of C-1209 dichloro-crosslinked dimer Complex
A mixed solution of iridium trichloride monohydrate (4.0g,13.4mmol), intermediate L-4(7.4g,29.5mmol) and diethanol monoethyl ether in 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 C-1209 dichloro-crosslinked dimer complex (6.1g, yield 62%). Mass spectrum m/z: theoretical value: 1454.6, respectively; measured value: 1455.22. the above results confirmed that the obtained product was the objective product.
Synthesis of C-1209
Dichloro-crosslinked dimer complex (3.2g,2.2mmol), 2-methyl-1, 3-dicyclohexyl-1, 3-propanedione (1.6g,6.5mmol), anhydrous sodium carbonate (1.1g,10.8mmol) 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 C-1209(2.7g, 65% yield) as the desired product. Mass spectrum m/z: theoretical value: 940.40, respectively; measured value: 941.02. the above results confirmed that the obtained product was the objective product.
Example 5
Synthesis of C-1210 dichloro-crosslinked dimer Complex
A mixed solution of iridium trichloride monohydrate (4.0g,13.4mmol), intermediate L-5(8.2g,29.5mmol) and diethanol monoethyl ether in a ratio of 3:1 to distilled water (120mL:40mL) 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 C-1210 dichloro-crosslinked dimer complex (6.5g, yield 62%). Mass spectrum m/z: theoretical value: 1558.83, respectively; measured value: 1559.45. the above results confirmed that the obtained product was the objective product.
Synthesis of C-1210
Dichloro-crosslinked dimer complex (3.4g,2.2mmol), 3-phenyl-2, 4-pentanedione (1.6g,6.5mmol), anhydrous sodium carbonate (1.2g,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 C-1210(2.6g, 65% yield) the desired product. Mass spectrum m/z: theoretical value: 918.16, respectively; measured value: 918.78. the above results confirmed that the obtained product was the objective product.
Example 6
Synthesis of dichloro-crosslinked dimer Complex to C-1215
A mixed solution of iridium trichloride monohydrate (4.0g,13.4mmol), intermediate L-6(7.4g,29.5mmol) and diethanol monoethyl ether in 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 C-1215 dichloro crosslinked dimer complex (6.0g, yield 62%). Mass spectrum m/z: theoretical value: 1450.57, respectively; measured value: 1451.19. the above results confirmed that the obtained product was the objective product.
Synthesis of C-1215
Dichloro-crosslinked dimer complex (3.2g,2.2mmol), 5-ethyl-2, 8-dimethyl-4, 6-nonanedione (1.4g,6.5mmol), anhydrous sodium carbonate (1.1g,10.8mmol) 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 C-1215(2.6g, 65% yield) as the desired product. Mass spectrum m/z: theoretical value: 900.14, respectively; measured value: 900.76. the above results confirmed that the obtained product was the objective product.
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, on the ITO substrate
And
the sequence of (a) and (b) forming layers of organic material. At 0.9mA, the luminance is equal to 1200cd/m2(6.1V). In this case, CIEx is 0.697 and y is 0.301.
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, on the ITO substrate
And
the sequence of (a) and (b) forming layers of organic material. At 0.9mA, the luminance is equal to 1299cd/m2(6.2V). In this case, CIEx is 0.694 and y is 0.305.
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, on the ITO substrate
And
the sequence of (a) and (b) forming layers of organic material. At 0.9mA, the luminance is equal to 1242cd/m2(6.4V). At this time, CIEx is 0.692 and y is 0.306.
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, on the ITO substrate
And
the sequence of (a) and (b) forming layers of organic material. At 0.9mA, the luminance is equal to 1331cd/m2(6.3V). In this case, CIEx is 0.692 and y is 0.305.
Example 5
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, on the ITO substrate
And
the sequence of (a) and (b) forming layers of organic material. At 0.9mA, the luminance is equal to 1330cd/m2(6.4V). At this time, CIEx is 0.692 and y is 0.306.
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, on the ITO substrate
And
the sequence of (a) and (b) forming layers of organic material. At 0.9mA, the luminance is equal to 1331cd/m2(6.3V). In this case, CIEx is 0.692 and y is 0.307.
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, on the ITO substrate
And
the 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 (9)
1. A red phosphorescent compound is characterized in that the structural formula is shown as a formula I,
wherein A is independently selected from substituted or unsubstituted C6-C30 naphthyridine;
wherein R is1、R2、R3、R4、R5And R6Independently selected from one of hydrogen, deuterium, halogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C5-C8 cycloalkyl and substituted or unsubstituted C6-C30 aryl; x1、X2、X3And X4Selected from C or N; n is selected from 1 or 2.
2. The red phosphorescent compound of claim 1, wherein the alkyl group having 1-6 carbon atoms or the cycloalkyl group having 5-8 carbon atoms is selected from one of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, n-pentyl, cyclopentyl and cyclohexyl.
3. The red phosphorescent compound according to claim 2, wherein the hydrogen atoms of the alkyl group having 1 to 6 carbon atoms or the cycloalkyl group having 5 to 8 carbon atoms are each replaced by a deuterium atom.
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 L isbThe group is selected from one of the following structural formulas:
6. the red phosphorescent compound of claim 1, wherein formula (i) is any one of the following structural formulae:
7. 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 6 as a dopant.
8. The organic electroluminescent device as claimed in claim 7, wherein any one of an Al metal complex, a Zn metal complex, and a carbazole derivative is used as a host material of the light emitting layer, and wherein the dopant is used in an amount ranging from 0.1% to 50% by weight.
9. The organic electroluminescent device as claimed in claim 8, wherein the ligand of each of the Al metal complex, Zn metal complex includes quinolyl, biphenyl, isoquinolyl, phenyl, methylquinolyl, dimethylquinolyl, dimethylisoquinolyl; carbazole derivatives include CBP.
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| WO2022083779A1 (en) * | 2020-10-23 | 2022-04-28 | 北京绿人科技有限责任公司 | Compound containing 1,3-diketone ligand and application thereof, and organic electroluminescent device |
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| WO2022083779A1 (en) * | 2020-10-23 | 2022-04-28 | 北京绿人科技有限责任公司 | Compound containing 1,3-diketone ligand and application thereof, and organic electroluminescent device |
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