CN110615816A - Phosphorescent material, preparation method thereof and organic electroluminescent device containing phosphorescent material - Google Patents
Phosphorescent material, preparation method thereof and organic electroluminescent device containing phosphorescent material Download PDFInfo
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- 239000000463 material Substances 0.000 title claims abstract description 53
- 238000002360 preparation method Methods 0.000 title claims description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 239000000126 substance Substances 0.000 claims abstract description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 40
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 239000010410 layer Substances 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- 235000019441 ethanol Nutrition 0.000 claims description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000002950 monocyclic group Chemical group 0.000 claims description 8
- 125000003367 polycyclic group Chemical group 0.000 claims description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 7
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 claims description 6
- 239000012046 mixed solvent Substances 0.000 claims description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 6
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000001769 aryl amino group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- -1 cyano, carboxyl Chemical group 0.000 claims description 4
- 239000002019 doping agent Substances 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 239000012044 organic layer Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Chemical group 0.000 claims description 4
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- 229910052717 sulfur Chemical group 0.000 claims description 3
- 125000006746 (C1-C60) alkoxy group Chemical group 0.000 claims description 2
- 125000006818 (C3-C60) cycloalkyl group Chemical group 0.000 claims description 2
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 2
- 125000006752 (C6-C60) arylthio group Chemical group 0.000 claims description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000000707 boryl group Chemical group B* 0.000 claims description 2
- CZKMPDNXOGQMFW-UHFFFAOYSA-N chloro(triethyl)germane Chemical compound CC[Ge](Cl)(CC)CC CZKMPDNXOGQMFW-UHFFFAOYSA-N 0.000 claims description 2
- 229940125904 compound 1 Drugs 0.000 claims description 2
- 229940125782 compound 2 Drugs 0.000 claims description 2
- 229940126214 compound 3 Drugs 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052805 deuterium Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 238000002156 mixing Methods 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
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 1
- 239000005864 Sulphur Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 abstract description 7
- 239000003446 ligand Substances 0.000 abstract description 5
- 150000002736 metal compounds Chemical class 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 21
- 239000007787 solid Substances 0.000 description 13
- 239000003208 petroleum Substances 0.000 description 12
- 239000002994 raw material Substances 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000012544 monitoring process Methods 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 238000005406 washing Methods 0.000 description 10
- 238000001035 drying Methods 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 238000000967 suction filtration Methods 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000004020 luminiscence type Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- MNKYQPOFRKPUAE-UHFFFAOYSA-N chloro(triphenyl)silane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 MNKYQPOFRKPUAE-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- KDOQMLIRFUVJNT-UHFFFAOYSA-N 4-n-naphthalen-2-yl-1-n,1-n-bis[4-(n-naphthalen-2-ylanilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=C(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=C1 KDOQMLIRFUVJNT-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 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
- 230000003595 spectral effect Effects 0.000 description 1
- 238000005303 weighing 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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- H—ELECTRICITY
- 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
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
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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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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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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
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
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- 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
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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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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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
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- Optics & Photonics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to a phosphorescent material and an organic electroluminescent device containing the same, and relates to the field of organic luminescent materials. The structural formula of the phosphorescent material is shown in chemical formula 1:
Description
Technical Field
The invention relates to the field of organic luminescent materials, in particular to a phosphorescent material, a preparation method thereof and an organic electroluminescent device containing the phosphorescent material.
Background
The OLED display is a display made using organic electroluminescent diodes. The display panel has the excellent characteristics of self-luminescence, no need of backlight source, high contrast, thin thickness, wide viewing angle, high reaction speed, wide application temperature range, simple structure and process, and the like, and can be used for a flexible panel, so the display panel is considered as a new application technology of a next-generation flat panel display.
The phosphorescence emission phenomenon is well-traced since the discovery, because the luminous efficiency of the phosphorescence material is obviously higher than the fluorescence emission efficiency, the phosphorescence emission device has more advantages compared with the traditional fluorescent material which is a light-emitting device, because the phosphorescence emission device can simultaneously capture singlet excitons and triplet excitons excited by an electric field, the internal quantum efficiency of the phosphorescence emission device can break the theoretical limit of 25 percent based on the fluorescent material device, and 100 percent of the internal quantum efficiency is possible. Therefore, many research institutes are increasing the research and development efforts of phosphor materials, and trying to accelerate the development of industrialization through phosphor materials. However, the phosphor material has high synthesis cost, high synthesis process requirement, high purification requirement, short service life and low efficiency, and is easy to pollute the environment in the synthesis process.
Therefore, the above problems are urgently needed to be improved, and the use of phosphorescent materials is needed to be solved and advanced.
Disclosure of Invention
In view of the above-mentioned deficiencies of the prior art, the present invention provides a phosphorescent material, a method for preparing the same, and an organic electroluminescent device comprising the same. The phosphorescent material provided by the invention has the advantages that the specific heterocyclic ligand combination is selected, the wavelength of the compound is adjusted, and the obtained organic metal compound is used for an organic electroluminescent device, so that the luminous efficiency of the device is improved, and the service life is long.
In order to solve the technical problems, the technical scheme of the invention is as follows:
the invention provides a phosphorescent material, which has a structural formula shown in chemical formula 1:
wherein R is1～R3Each independently represents hydrogen, deuterium, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heterocyclic group, a substituted or unsubstituted C1-C60 alkylamino group, or a substituted or unsubstituted C6-C60 arylamino group;
R4～R7each independently represents: hydrogen, isotopes of hydrogen, halogen, cyano, carboxyl, nitro, hydroxyl, sulfonic acid, phosphoric acid, boryl, substituted or unsubstituted silyl, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, substituted or unsubstituted C3-C60 cycloalkyl, substituted or unsubstituted C1-C60 alkoxy, substituted or unsubstituted C1-C60 alkylamino, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C6-C60 aryloxy, or substituted or unsubstituted C6-C60 arylthio; or are linked to an adjacent substituent(s) to form a substituted or unsubstituted, mono-or polycyclic, specifically aliphatic or aromatic ring of C3-C30;
l is a connecting bond or is selected from substituted or unsubstituted alkyl of C1-C60, cycloalkyl of C3-C60, substituted or unsubstituted aryl of C6-C60, or heterocyclic group of C6-C60; or are linked to an adjacent substituent(s) to form a substituted or unsubstituted, mono-or polycyclic, specifically aliphatic or aromatic ring of C3-C30;
ar is substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heterocyclic group, substituted or unsubstituted C1-C60 alkylamino, or substituted or unsubstituted C6-C60 arylamino; preferably a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heterocyclic group, or a substituted or unsubstituted C6-C60 arylamino group;
R4～R7at any position of the ring; r4、R5The number of (A) is 0-4; r6、R7The number of (A) is 0-3;
n is an integer of 0 to 3.
In the above-mentioned embodiments, L is preferably a bond or a phenyl group.
In the above technical scheme, when L is linked to an adjacent substituent to form a substituted or unsubstituted monocyclic or polycyclic ring, the carbon atom thereof may be replaced with at least one hetero atom selected from nitrogen, oxygen, sulfur.
In the above technical scheme, when R is4～R7When linked to an adjacent substituent to form a substituted or unsubstituted monocyclic or polycyclic ring, respectively, the carbon atom may be replaced with at least one heteroatom selected from nitrogen, oxygen, sulfur.
In the above technical solution, it is most preferable that the phosphorescent material is selected from any one of the following structures:
the invention also provides a preparation method of the phosphorescent material, which comprises the following steps:
step 1, preparation of intermediate I
Dissolving compound 1 and compound 2 in a mixed solvent of toluene, ethanol and water, and adding Pd (PPh)3)4、K2CO3After the reaction is finished, preparing an intermediate I;
step 2, preparation of intermediate II
Dissolving compound 3 and compound 4 in a mixed solvent of toluene, ethanol and water, and adding Pd (PPh)3)4、K2CO3After the reaction is finished, preparing an intermediate II;
step 3, preparation of intermediate IV
Reacting intermediate II with IrCl3·3H2Mixing O, heating, and preparing an intermediate III after the reaction is finished; dissolving the intermediate III in dichloromethane, adding an isopropanol solution of silver trifluoromethanesulfonate, and preparing an intermediate IV after the reaction is finished;
step 4, preparation of compound shown in chemical formula 1
Adding absolute ethyl alcohol into the intermediate IV and the intermediate I, and preparing a compound shown in a chemical formula 1 after the reaction is finished;
in the formula: r1～R7The definitions of the substituents and the number of substituents, L, Ar, and n are the same as those in chemical formula 1, and are not repeated herein.
In the above preparation method, the preferred solvent for the synthesis of intermediates I and II is a mixed solvent of toluene, ethanol and water in a molar ratio of 1: 2-3: 2-3, the reaction temperature is not more than 100 ℃, and the reaction time is not more than 24 hours. IrCl3·3H2O and intermediate II in a molar ratio of 1: 2-4 are mixed in a solvent and the mixture is heated under reflux prior to isolation of the diiridium dimer. In the preparation of the compound of formula 1, preferred solvents are alcohols or alcohol/water mixed solvents, such as ethanol and ethanol/water mixtures. Final productThe molar ratio of primary ligand to secondary ligand is determined based on the approximate molar ratio of the reactants (based on composition).
The present invention also provides an organic electroluminescent device prepared from the phosphorescent material represented by chemical formula 1 of the present invention.
The organic electroluminescent device comprises: the organic light emitting diode comprises a first electrode, a second electrode and an organic layer arranged between the two electrodes, wherein the organic layer contains the phosphorescent material shown in the chemical formula 1.
The organic electroluminescent device includes a light emitting layer containing a phosphorescent material represented by chemical formula 1 of the present invention.
The light emitting layer of the organic electroluminescent device includes a host material and a dopant material containing a phosphorescent material represented by chemical formula 1 of the present invention.
The invention has the beneficial effects that:
the phosphorescent material provided by the invention has the advantages that the specific heterocyclic ligand combination is selected, the wavelength of the compound is adjusted, and the obtained organic metal compound is used for an organic electroluminescent device, so that the luminous efficiency of the device is improved, and the service life is long.
The preparation method of the phosphorescent material provided by the invention has the advantages of easily available raw materials, simple synthesis process and higher product yield.
The phosphorescent material of the present invention can be applied to an OLED light emitting device, and compared to comparative examples, voltage, efficiency and lifetime are improved compared to known OLED materials.
Detailed Description
The following are examples of the present invention, which are provided to aid understanding of the present invention and are not intended to limit the scope of the present invention. In addition, the preparation methods of the compounds which are not specifically listed in the embodiments of the present invention are methods generally applied in the related industries, and the methods described in the embodiments can be referred to when preparing other compounds.
Example 1: compound PD10
Synthesis of intermediate 10-3
Accurately weighing 20g (67.8mmol) of triphenylchlorosilane, adding the triphenylchlorosilane into a reaction bottle, adding 300mL of toluene, 150mL of ethanol and 150mL of deionized water, stirring for 30 minutes under the protection of nitrogen, and then respectively adding 16.2 g (81.4mmol) of raw material 2-phenylpyridine (4-boric acid) and catalyst Pd (PPh)3)40.6 g (0.678mol), 18.57 g of potassium carbonate (134.6mmol) were heated to 90 ℃ and reacted for 24 hours.
And (3) post-treatment process: TLC monitoring until the reaction is finished. Cooling, standing, separating, removing water layer, and keeping toluene layer. The toluene layer was washed once with 150mL of water, separated, dried, and spun dried to give a dark solid. Passing through a silica gel column, first eluting with dichloromethane: petroleum ether is 1: about 4 mL of the impurity spot was washed out, and then ethyl acetate: petroleum ether is 3: about 1 mL of the product was flushed out to obtain a complete product dot, which was then spun dry to obtain a white solid. 18g of product are obtained, yield 65%.
Synthesis of intermediate 10-6
Adding 20g (85.4mmol) of raw material 4-bromophenyl-2-pyridine and 12.5 g (10.25mmol) of phenylboronic acid into a reaction bottle, adding 200mL of toluene, 100mL of ethanol and 100mL of deionized water, adding catalyst Pd (PPh) under the protection of nitrogen, and adding catalyst Pd (PPh)3)40.1 g (0.854mol), 23.51 g potassium carbonate (0.1708mmol) were heated to 90 ℃ and reacted for 24 hours.
TLC monitoring until the reaction is finished. Cooling, standing, separating, removing water layer, and keeping toluene layer. The toluene layer was washed once with 200mL of water, separated, dried and spun dry to give a dark solid. Passing through a silica gel column, first eluting with dichloromethane: petroleum ether is 1: about 4 mL of the impurity spot was washed out, and then ethyl acetate: petroleum ether is 2: about 1 mL of the product was flushed out to give a white solid. 15g of product are obtained with a yield of 70%.
Synthesis of intermediate 10-7
Adding 10-313.6 g (32.88mmol) of intermediate and 3.4 g (13.15mmol) of iridium trichloride into a three-neck flask, adding 200mL of ethylene glycol diethyl ether and 100mL of water, heating to 140 ℃ under the protection of nitrogen, and stirring for reacting for 24 hours.
After 1 hour of reaction, a solid precipitated and the reaction was continued for 18 hours. And monitoring the reaction by TLC, and cooling after the raw materials are reacted. Directly filtering to obtain yellow solid, washing with 100mL of ethanol, washing with 100mL of petroleum ether, and drying. 12.11g of product was obtained, yield: 70% and MW: 2104.47.
Synthesis of intermediate 10-8
10-712.11 g (5.75mol) of intermediate was charged into a three-necked flask, and about 200mL of methylene chloride was added thereto, followed by stirring at room temperature until all the intermediate was dissolved. 4.6 g (17.25mmol) of silver triflate were dissolved in 20mL of isopropanol. The prepared isopropanol solution is dripped into a three-neck flask and reacted for 24 hours at room temperature.
TLC monitoring, the basic reaction of the raw materials is finished, the deep color solution is obtained by suction filtration, the deep color oily matter is obtained by spin drying, and the yield is 100%. MW:1286.33
Synthesis of Compound PD10
10-87.4 g (5.75mol) of intermediate was put into a three-necked flask, 150mL of anhydrous ethanol and 10-69.6 g (11.5mmol) of intermediate were added thereto, and the reaction mixture was stirred at 90 ℃ for 24 hours, whereupon a large amount of solid was precipitated.
TLC monitoring, the raw materials are basically reacted. Suction filtration to obtain the target product, washing with about 50mL of petroleum ether, drying to obtain 5.6 g of product, yield 76%, and HPLC 99%. MW: 1280.17.
Example 2: compound PD25
Intermediate 25-8 was synthesized according to the procedure of example 1.
Intermediate 25 to 812.87 g (10.0mmol) was put into a three-necked flask, and 150mL of absolute ethanol and intermediate 25 to 65.22 g (20.0mmol) were further added, and the reaction mixture was stirred at 90 ℃ for 24 hours, whereupon a large amount of solid precipitated. TLC monitoring, the raw materials are basically reacted. Suction filtration to obtain the target product, washing with about 50mL of petroleum ether, and drying to obtain 9.2g of product with 72% yield, which is measured as 99% HPLC. MW: 1277.52.
Example 3: compound PD34
Intermediate 34-812.87 g (10.0mmol) was added to a three-necked flask, 150mL of anhydrous ethanol and intermediate 34-66.18 g (20mmol) were further added, and the reaction was stirred at 90 ℃ for 24 hours, whereupon a large amount of solid precipitated.
TLC monitoring, the raw materials are basically reacted. Suction filtration to obtain the target product, washing with about 50mL petroleum ether, drying to obtain product PD3410.34g, yield 78%, HPLC 99%. MW: 1325.41.
Example 4: compound PD47
Intermediate 47-812.87 g (10.0mmol) was added to a three-necked flask, 150mL of anhydrous ethanol and intermediate 47-69.96 g (20mmol) were further added, and the reaction mixture was stirred at 90 ℃ for 24 hours, whereupon a large amount of solid precipitated. TLC monitoring, the raw materials are basically reacted. And (4) performing suction filtration to obtain a target product crude product, washing with about 50mL of petroleum ether, and drying to obtain a product PD4710.35g, wherein the yield is 72%, and the HPLC is 99%. MW: 1438.40.
Example 5: compound PD59
Intermediate 59-813.9 g (10.0mmol) was charged into a three-necked flask, 150mL of anhydrous ethanol and intermediate 59-66.42 g (20mmol) were further added, and the reaction mixture was stirred at 90 ℃ for 24 hours, whereupon a large amount of solid precipitated. TLC monitoring, the raw materials are basically reacted. And (4) performing suction filtration to obtain a target product crude product, washing with about 50mL of petroleum ether, and drying to obtain a product PD5911.21g, wherein the yield is 78%, and the HPLC is 99%. MW: 1437.49.
Example 6: compound PD69
Intermediate 69-812.87 g (10.0mmol) was charged into a three-necked flask, 150mL of anhydrous ethanol and intermediate 69-66.94 g (20.0mol) were further added, and the mixture was stirred at 90 ℃ for 24 hours to precipitate a large amount of solid. TLC monitoring, the raw materials are basically reacted. Suction filtration to obtain the target product, washing with about 50mL of petroleum ether, and drying to obtain 9.95g of product with 73% yield, which is measured as 99% HPLC. MW: 1363.12.
EXAMPLE 7 Compound PD7
Synthesis of Compound PD7
10-87.4 g (5.75mol) of intermediate was put into a three-necked flask, 150mL of anhydrous ethanol and 10-34.8 g (11.5mmol) of intermediate were added thereto, and the reaction mixture was stirred at 90 ℃ for 24 hours, whereupon a large amount of solid was precipitated.
TLC monitoring, the raw materials are basically reacted. Suction filtration is carried out to obtain a target product, about 50mL of petroleum ether is used for washing, and the product is dried to obtain 5.6 g, the yield is 80%, and the HPLC is measured to be 99.1%. MW: 1432.
The present invention also provides an organic electroluminescent device made of the phosphorescent material of the present invention represented by chemical formula 1.
In order to further describe the present invention, more specific examples are set forth below.
Example 8
Organic electroluminescent devices were prepared using phosphorescent materials of formula PD10, which is more specific:
coating with a thickness ofThe ITO glass substrate of (1) was washed in distilled water for 2 times, ultrasonically for 30 minutes, repeatedly washed in distilled water for 2 times, ultrasonically for 10 minutes, and after the washing with distilled water was completed, solvents such as isopropyl alcohol, acetone, and methanol were ultrasonically washed in this order, dried, transferred to a plasma cleaning machine, and the substrate was washed for 5 minutes and sent to an evaporation coater. Firstly, evaporating N1- (2-naphthyl) -N4, N4-di (4- (2-naphthyl (phenyl) amino) phenyl) -N1-phenyl benzene-1, 4-diamine ('2-TNATA') 60nm on an ITO (anode), and then evaporating NPB 60nm, a host substance 4,4'-N, N' -biphenyl dicarbazole ('CBP') and a doping substance compound PD 1095: 5 in a weight ratio of 30nm in mixed evaporation, 10nm in thickness of a hole blocking layer ('BALq') in evaporation, 40nm in thickness of an electron transport layer ('Alq 3') in evaporation, 0.2nm in thickness of an electron injection layer in evaporation and 150nm in Al in evaporation of a cathode to prepare the organic electroluminescent device. And testing the performance luminescence characteristics of the obtained device, wherein a KEITHLEY 2400 type source measuring unit and a CS-2000 spectral radiance luminance meter are adopted for measurement so as to evaluate the driving voltage, the luminescence brightness and the luminescence efficiency.
Example 9
An organic electroluminescent device was produced as in example 8, except that the light-emitting layer doping compound was replaced with the compound PD25 from the compound PD 10.
Example 10
An organic electroluminescent device was produced as in example 8, except that the light-emitting layer doping compound was replaced with the compound PD34 from the compound PD 10.
Example 11
An organic electroluminescent device was produced as in example 8, except that the light-emitting layer doping compound was replaced with the compound PD47 from the compound PD 10.
Example 12
An organic electroluminescent device was produced as in example 8, except that the light-emitting layer doping compound was replaced with the compound PD59 from the compound PD 10.
Example 13
An organic electroluminescent device was produced as in example 8, except that the light-emitting layer doping compound was replaced with the compound PD69 from the compound PD 10.
Example 14
An organic electroluminescent device was produced as in example 8, except that the light-emitting layer doping compound was replaced with the compound PD7 from the compound PD 10.
Comparative example 1
An organic electroluminescent device was produced in the same manner as in example 8, except that the dopant compound was replaced with the compound PD10 as follows:
table 1 results of testing organic electroluminescent elements in examples 8 to 14 and comparative example 1
| Compound (I) | Driving voltage (v) | Efficiency of | Life (h) | Colour(s) |
| Ir(ppy)3 | 1.0 | 1.0 | 1.0 | Green |
| PD10 | 0.57 | 3.9 | 5.2 | Green |
| PD24 | 0.55 | 3.9 | 4.7 | Green |
| PD34 | 0.56 | 3.8 | 5.5 | Green |
| PD47 | 0.53 | 3.7 | 5.0 | Green |
| PD59 | 0.56 | 3.8 | 4.9 | Green |
| PD69 | 0.55 | 3.8 | 5.1 | Green |
| PD7 | 0.54 | 3.8 | 4.8 | Green |
The device test performance was measured by referring to comparative device 1, and each performance index of comparative device 1 was set to 1.0. From the results of table 1, it can be seen that the phosphorescent material of the present invention can be applied to an OLED light emitting device, and compared to the comparative example, the voltage, efficiency and lifetime are improved compared to the known OLED material.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.
Claims (10)
1. A phosphorescent material, characterized in that its structural formula is shown in chemical formula 1:
wherein R is1～R3Each independently represents hydrogen, deuterium, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heterocyclic group, a substituted or unsubstituted C1-C60 alkylamino group, or a substituted or unsubstituted C6-C60 arylamino group;
R4～R7each independently represents: hydrogen, isotopes of hydrogen, halogens, cyano, carboxyl, nitro, hydroxy, sulfonic acidsA group, a phosphoric acid group, a boryl group, a substituted or unsubstituted silicon group, a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C3-C60 heteroaryl group, a substituted or unsubstituted C3-C60 cycloalkyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C1-C60 alkylamino group, a substituted or unsubstituted C6-C60 arylamino group, a substituted or unsubstituted C6-C60 aryloxy group, or a substituted or unsubstituted C6-C60 arylthio group; or are linked to an adjacent substituent(s) to form a substituted or unsubstituted, mono-or polycyclic, specifically aliphatic or aromatic ring of C3-C30;
l is a connecting bond or is selected from substituted or unsubstituted alkyl of C1-C60, cycloalkyl of C3-C60, substituted or unsubstituted aryl of C6-C60, or heterocyclic group of C6-C60; or are linked to an adjacent substituent(s) to form a substituted or unsubstituted, mono-or polycyclic, specifically aliphatic or aromatic ring of C3-C30;
ar is substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heterocyclic group, substituted or unsubstituted C1-C60 alkylamino, or substituted or unsubstituted C6-C60 arylamino; r4～R7At any position of the ring; r4、R5The number of (A) is 0-4; r6、R7The number of (A) is 0-3;
n is an integer of 0 to 3.
2. The phosphorescent material of claim 1, wherein L is a bond or a phenyl group.
3. The phosphorescent material of claim 1, wherein when L is linked to an adjacent substituent to form a substituted or unsubstituted mono-or polycyclic ring, the carbon atom thereof is replaced with at least one heteroatom selected from nitrogen, oxygen, and sulfur.
4. The phosphorescent material of claim 1, wherein when R is4～R7When linked to adjacent substituents to form a substituted or unsubstituted monocyclic or polycyclic ring, respectively,the carbon atoms of which are replaced by at least one heteroatom selected from nitrogen, oxygen, sulphur.
5. The phosphorescent material of claim 1, wherein the phosphorescent material is selected from any one of the following structures:
6. a method for preparing a phosphorescent material according to any one of claims 1 to 5, characterized by comprising the steps of:
step 1, preparation of intermediate I
Dissolving compound 1 and compound 2 in a mixed solvent of toluene, ethanol and water, and adding Pd (PPh)3)4、K2CO3After the reaction is finished, preparing an intermediate I;
step 2, preparation of intermediate II
Dissolving compound 3 and compound 4 in a mixed solvent of toluene, ethanol and water, and adding Pd (PPh)3)4、K2CO3After the reaction is finished, preparing an intermediate II;
step 3, preparation of intermediate IV
Will be intermediateBody II and IrCl3·3H2Mixing O, heating, and preparing an intermediate III after the reaction is finished; dissolving the intermediate III in dichloromethane, adding an isopropanol solution of silver trifluoromethanesulfonate, and preparing an intermediate IV after the reaction is finished;
step 4, preparation of compound shown in chemical formula 1
Adding absolute ethyl alcohol into the intermediate IV and the intermediate I, and preparing a compound shown in a chemical formula 1 after the reaction is finished;
7. an organic electroluminescent device prepared from the phosphorescent material of any one of claims 1 to 5.
8. The organic electroluminescent device according to claim 7, comprising: a first electrode, a second electrode and an organic layer disposed between the two electrodes, wherein the organic layer contains the phosphorescent material according to any one of claims 1 to 5.
9. The organic electroluminescent device according to claim 8, comprising a light-emitting layer containing the phosphorescent material according to any one of claims 1 to 5.
10. The organic electroluminescent device according to claim 9, wherein the light-emitting layer comprises a host material and a dopant material, and the dopant material contains the phosphorescent material according to any one of claims 1 to 5.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3904363A1 (en) * | 2020-04-29 | 2021-11-03 | Samsung Electronics Co., Ltd. | Organometallic compound, organic light-emitting device including the same, and electronic apparatus including the organic light-emitting device |
| EP3974494A1 (en) * | 2020-09-29 | 2022-03-30 | Samsung Electronics Co., Ltd. | Organometallic compound, organic light-emitting device including the same, and electronic apparatus including the organic light-emitting device |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140008617A1 (en) * | 2012-07-09 | 2014-01-09 | Universal Display Corporation | Novel silylated metal complexes |
| KR20170082236A (en) * | 2016-01-06 | 2017-07-14 | 부산대학교 산학협력단 | organic light-emitting diodes |
| CN107759638A (en) * | 2016-08-19 | 2018-03-06 | 株式会社Lg化学 | New organo-metallic compound and utilize its organic illuminating element |
-
2019
- 2019-10-16 CN CN201910982890.3A patent/CN110615816B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20140008617A1 (en) * | 2012-07-09 | 2014-01-09 | Universal Display Corporation | Novel silylated metal complexes |
| KR20170082236A (en) * | 2016-01-06 | 2017-07-14 | 부산대학교 산학협력단 | organic light-emitting diodes |
| CN107759638A (en) * | 2016-08-19 | 2018-03-06 | 株式会社Lg化学 | New organo-metallic compound and utilize its organic illuminating element |
Non-Patent Citations (1)
| Title |
|---|
| GUIJIANG ZHOU等: "Robust Tris-Cyclometalated Iridium(III) Phosphors with Ligands for Effective Charge Carrier Injection/Transport: Synthesis, Redox, Photophysical, and Electrophosphorescent Behavior", 《CHEM. ASIAN J.》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3904363A1 (en) * | 2020-04-29 | 2021-11-03 | Samsung Electronics Co., Ltd. | Organometallic compound, organic light-emitting device including the same, and electronic apparatus including the organic light-emitting device |
| EP3974494A1 (en) * | 2020-09-29 | 2022-03-30 | 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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