CN111253440A - Phosphorescent compound and preparation method and application thereof - Google Patents
Phosphorescent compound and preparation method and application thereof Download PDFInfo
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- CN111253440A CN111253440A CN201911348513.0A CN201911348513A CN111253440A CN 111253440 A CN111253440 A CN 111253440A CN 201911348513 A CN201911348513 A CN 201911348513A CN 111253440 A CN111253440 A CN 111253440A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 56
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 239000003446 ligand Substances 0.000 claims abstract description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 42
- 229910052757 nitrogen Inorganic materials 0.000 claims description 38
- 238000006243 chemical reaction Methods 0.000 claims description 24
- -1 cyano, carboxyl Chemical group 0.000 claims description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 14
- 229910052711 selenium Inorganic materials 0.000 claims description 12
- 229910052710 silicon Inorganic materials 0.000 claims description 12
- 229910052805 deuterium Inorganic materials 0.000 claims description 10
- LNJXVUXPFZKMNF-UHFFFAOYSA-K iridium(3+);trichloride;trihydrate Chemical compound O.O.O.Cl[Ir](Cl)Cl LNJXVUXPFZKMNF-UHFFFAOYSA-K 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- CZKMPDNXOGQMFW-UHFFFAOYSA-N chloro(triethyl)germane Chemical compound CC[Ge](Cl)(CC)CC CZKMPDNXOGQMFW-UHFFFAOYSA-N 0.000 claims description 9
- 239000012046 mixed solvent Substances 0.000 claims description 9
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 9
- 125000000707 boryl group Chemical group B* 0.000 claims description 8
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- AEDZKIACDBYJLQ-UHFFFAOYSA-N ethane-1,2-diol;hydrate Chemical compound O.OCCO AEDZKIACDBYJLQ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 239000013067 intermediate product Substances 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 4
- 125000006746 (C1-C60) alkoxy group Chemical group 0.000 claims description 4
- 125000006818 (C3-C60) cycloalkyl group Chemical group 0.000 claims description 4
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 4
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 4
- 125000006752 (C6-C60) arylthio group Chemical group 0.000 claims description 4
- 229940126062 Compound A Drugs 0.000 claims description 4
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 125000003367 polycyclic group Chemical group 0.000 claims description 4
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical group [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000006549 C4-C10 aryl group Chemical group 0.000 claims 1
- 229910052741 iridium Inorganic materials 0.000 abstract description 4
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 3
- 229910052751 metal Inorganic materials 0.000 abstract description 3
- 239000002184 metal Substances 0.000 abstract description 3
- 150000002736 metal compounds Chemical class 0.000 abstract description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 abstract 2
- 238000009776 industrial production Methods 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
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- 230000000052 comparative effect Effects 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 238000004020 luminiscence type Methods 0.000 description 5
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 2
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 2
- PKMUHQIDVVOXHQ-HXUWFJFHSA-N C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O Chemical compound C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O PKMUHQIDVVOXHQ-HXUWFJFHSA-N 0.000 description 2
- 108700042658 GAP-43 Proteins 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229940126208 compound 22 Drugs 0.000 description 2
- 229940127573 compound 38 Drugs 0.000 description 2
- 229940126179 compound 72 Drugs 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 230000003595 spectral effect Effects 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
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-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
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 230000000007 visual effect Effects 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
-
- 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
-
- 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)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention discloses a phosphorescent compound and a preparation method and application thereof, and an organic metal iridium complex disclosed by the invention is prepared by combining metal iridium with a specific heterocyclic ligand, and the specific structural general formula is shown in the specification. By adjusting the wavelength of the compound, 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 is simple and easy to operate, and is more suitable for large-scale industrial production.
Description
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to a phosphorescent compound, a preparation method thereof and an organic electroluminescent device containing the phosphorescent compound.
Background
The OLED is a hole and electron dual injection type light emitting device, and directly converts electric energy into light energy of organic semiconductor material molecules. Compared with traditional display devices such as CRT, LCD, PDP and the like, OLED (organic light emitting semiconductor) has all advantages of the existing display, has unique advantages, not only has high brightness, high contrast, high definition, wide visual angle, wide color gamut and the like to realize high-quality images, but also has the characteristics of ultra-thin, ultra-light, low driving voltage, low power consumption, wide temperature and the like to meet the requirements of portable equipment on portability, power saving and outdoor operation; the OLED display has the unique characteristics of self-luminescence, high luminous efficiency, short response time, transparency, flexibility and the like.
The noble metal complex is used as a phosphorescent material, singlet excitons and triplet excitons are fully utilized, and compared with a fluorescent material, only the singlet excitons are utilized, and the triplet excitons with the proportion up to 75 percent are effectively utilized, so that the PhOLED based on the phosphorescent material realizes 100 percent of internal quantum efficiency. In recent three years, phosphorescent materials gradually replace traditional fluorescent materials, and become hot spots for research on OLED luminescent materials. However, the synthesis process of the phosphorescent material is complex, takes long time and has short service life.
Therefore, it is an urgent need to solve the problems of the prior art to provide a phosphorescent compound having high device luminous efficiency, long lifetime and simple synthesis process, and a method for preparing the same.
Disclosure of Invention
In view of the above, the present invention provides a phosphorescent compound, a preparation method thereof and an application thereof, in which the wavelength of the compound is adjusted by selecting a specific heterocyclic ligand combination, and the obtained organometallic compound is used in an organic electroluminescent device, so that the luminous efficiency of the device is improved, and the service life of the device is long.
In order to achieve the purpose, the invention adopts the following technical scheme: a phosphorescent compound, characterized in that the general structural formula of the phosphorescent compound is:
wherein n is 1 or 2;
R1is at any position of the ring; r2Is at any position on ring Ar.
R1-R2As follows: any one of hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, sulfonic acid group, phosphoric acid group, borane group, C1-C20 alkyl, C6-C60 aryl, C3-C60 heteroaryl, C3-C60 cycloalkyl, C1-C60 alkoxy, C1-C60 alkylamino, C6-C60 arylamino, C6-C60 aryloxy, C6-C60 arylthio;
ar is a five-membered ring or a six-membered ring;
X1、X2are all O, S, N, Se, Si, NR1、NR2、CR1R2、Se、SiR1R2Any one of (1);
X3-6、X9-10all are any one or more of C, O, S, N, Se and Si;
X7、X8all are any one or more of C, O, S, N, Se and Si, and at least one of the C, O, S, N, Se and Si is N;
the structural general formula of L is as follows:
wherein R is3At any position on ring Ar, R4Is at any position of the ring;
R3、R4any one of hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, sulfonic acid group, phosphoric acid group, boryl, C1-C20 alkyl, C6-C60 aryl, C3-C60 heteroaryl, C3-C60 cycloalkyl, C1-C60 alkoxy, C1-C60 alkylamino, C6-C60 arylamino, C6-C60 aryloxy and C6-C60 arylthio;
ar is a five-membered ring or a six-membered ring. .
The invention has the beneficial effects that: the invention selects the ligand combination of a specific heterocycle to adjust the wavelength of the compound, and the obtained organic metal compound is used in an organic electroluminescent device, so that the luminous efficiency of the device is improved, and the phosphorescent compound has long service life.
Preferably, said R is1、R2Deuterium, fluorine atom, cyano, carboxyl, nitro, hydroxyl, sulfonic acid group, phosphoric acid group, boryl, C1-C10 alkyl, C6-C18 aryl, C3-C20 heteroaryl; wherein, the heteroaryl contains or does not contain any one or more of O, S, N, Se and Si.
Preferably, R1-R4Are all linked to adjacent substituents to form a monocyclic or polycyclic ring.
Preferably, the first and second electrodes are formed of a metal,
the structural formula of (A) is:
preferably, in L1, R3、R4Deuterium, fluorine atom, alkyl group, cyano group, carboxyl group, nitro group, hydroxyl group, sulfonic group, phosphoric group, boryl group, C4-C10 aromatic ring; ar is a five-membered ring or a six-membered ring;
wherein, the aromatic ring contains or does not contain any one or more of O, S, N, Se and Si.
More preferably, L1 has the formula:
preferably, in L2, R3、R4All deuterium, fluorine atom, cyano, carboxyl, nitro, hydroxyl, sulfonic acid group, phosphoric acid group, boryl, C1-C10 alkyl, C6-C18 aryl, and C3-C20 heteroaryl;
wherein, the heteroaryl in the C3-C20 heteroaryl contains or does not contain one or more of O, S, N, Se and Si.
More preferably, L2 has the formula:
preferably, when n ═ 1, the L ligand is
The chemical formula I1Is composed of
When n is 2, the L ligand is
The chemical formula I2Is composed of
Preferably, the monocyclic ring and polycyclic ring are both C3-C30 aliphatic or aromatic rings.
Preferably, the five-membered ring or the six-membered ring contains or does not contain any one of O, S, N, Se and Si.
The following is the structure of a preferred phosphorescent compound:
the present invention also provides a method for preparing a phosphorescent compound, which is represented by formula I when n ═ 1,
the method comprises the following steps:
(1) under the protection of nitrogen, mixing the compound a with iridium trichloride trihydrate, and then adding the mixture into a mixed solvent of ethylene glycol ethyl ether and water for heating reaction to generate a bridging ligand b;
(2) mixing the bridging ligand b with silver trifluoromethanesulfonate, adding a mixed solvent of dichloromethane and methanol, and reacting at room temperature for 24 hours to generate an intermediate product c;
(3) mixing the intermediate product c with the compound d, adding ethanol, and stirring for reacting for 24 hours at 90 ℃ to obtain a compound of a chemical formula I;
wherein the molar ratio of the compound a to the iridium trichloride trihydrate is 12: 5; the molar ratio of the bridging ligand b to the silver trifluoromethanesulfonate is 2: 12; the molar ratio of the intermediate product c to the compound d is 12: 36;
in the step (1), the molar ratio of the volume of the mixed solvent to the iridium trichloride trihydrate is (200-300) mL: (25-30) mmol, wherein the solvent is a mixed solution of ethylene glycol ethyl ether and water, and the volume ratio of the ethylene glycol ethyl ether to the water is 15: 7;
in the step (2), the molar ratio of the volume of the mixed solvent to the silver trifluoromethanesulfonate is (100-200) mL: (20-25) mmol;
the synthetic route is as follows:
when n is 2, the preparation method of the chemical formula II,
the method comprises the following steps:
1) under the protection of nitrogen, the compound A and iridium trichloride trihydrate are mixed and then added into a mixed solvent of ethylene glycol ethyl ether and water for heating reaction to generate a bridging ligand B.
2) Mixing the bridging ligand B and the compound C, and stirring for 24 hours at room temperature under the protection of nitrogen for full reaction to prepare a compound of a chemical formula II;
wherein the molar ratio of the compound A to the iridium trichloride trihydrate is 12:5, and the molar ratio of the bridging ligand B to the compound C is 8: 6.
In the step (1), the molar ratio of the volume of the mixed solvent to the iridium trichloride trihydrate is (200-300) mL: (25-30) mmol, wherein the solvent is a mixed solution of ethylene glycol ethyl ether and water, and the volume ratio of the ethylene glycol ethyl ether to the water is 15: 7;
the synthetic route is
The preparation method has the advantages of simple synthesis process and high product yield.
The invention also discloses application of the organic iridium metal complex in an organic electroluminescent device.
The method specifically comprises the following steps: a first electrode, a second electrode, and one or more organic layers disposed between the first and second electrodes; wherein the organic layer contains the phosphorescent compound provided by the invention. The organic layer at least comprises one or more of a hole injection layer, a hole transport layer, a layer with hole injection and hole transport functions, an electron blocking layer, a light emitting layer, a hole blocking layer, an electron transport layer, an electron injection layer and a layer with electron transport and electron injection functions.
Specifically, the light-emitting layer is provided, and the light-emitting layer contains the phosphorescent compound provided by the invention.
The light-emitting layer comprises a main material and a doping material, the doping material is a phosphorescent compound provided by the invention, and the mass ratio of the main material to the phosphorescent compound is 90: 10-99.5: 0.5.
Detailed Description
The technical solutions in the embodiments of the present invention will be described clearly and completely with reference to the following embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
The synthesis route of the compound 1 is as follows:
the preparation method comprises the following steps:
1) weighing A-1(60mmol), IrC1 under nitrogen protection system3·3H2O (25mmo1) is put into a reaction system, a mixed solution of 150mL of ethylene glycol ethyl ether and 70mL of purified water is added, nitrogen is used for protection, and the temperature is raised to 140 ℃ to be stirred and reacted for 24 hours. The reaction was monitored by TLC and cooled to 30 ℃ until the reaction of the starting materials was complete. Direct suction filtration gave a yellow solid which was washed first with 100mL of ethanol and then with petroleum ether and dried under vacuum at 60 ℃ for 3 hours to give intermediate B-1(12.7g, 80% yield).
2) Intermediate B-1(8mmol) was weighed, silver trifluoromethanesulfonate (24mmol) was added, 100mL of dichloromethane was added to the system, 40mL of isopropanol was added, and the reaction was carried out at room temperature for 24 hours under nitrogen atmosphere. TLC monitored that the starting material was substantially reacted and the dark solution was filtered with suction to afford the compound of formula C-1 (12.3g, 88% yield).
3) Weighing the intermediate C-1(12mmol), adding the ligand D-1(36mmol), adding 150mL of absolute ethanol into the system, stirring and reacting at 90 ℃ for 24 hours under the protection of nitrogen, and separating out a large amount of solid. TLC monitoring, the raw materials are basically reacted. And (5) carrying out suction filtration to obtain a crude product of the target product. Washed with about 50mL of petroleum ether and dried to give compound 1(9.1g, 69% yield).
HPLC purity is more than 99%.
Mass spectrum calculated 1104.33; the test value was 1103.82.
Example 2:
the preparation of compound 22, the synthetic route is as follows:
the preparation method comprises the following steps:
1) weighing A-22(60mmol), IrC1 under nitrogen protection system3·3H2O (25mmo1, 4.4g) is put into a reaction system, a mixed solution of 150mL of ethylene glycol ethyl ether and 70mL of purified water is added, nitrogen is used for protection, and the temperature is raised to 140 ℃ and stirring reaction is carried out for 24 hours. The reaction was monitored by TLC and cooled to 30 ℃ until the starting material reaction was complete. Direct suction filtration gave a yellow solid which was washed first with 100mL of ethanol and then with 100mL of petroleum ether and dried under vacuum at 60 ℃ for 3 hours to give intermediate B-22(11.6g, 75% yield).
2) Intermediate B-22(8mmol) was weighed, silver trifluoromethanesulfonate (24mmol) was added, 100mL of dichloromethane and 40mL of isopropanol were added to the system, and the reaction was carried out at room temperature for 24 hours under nitrogen atmosphere. TLC monitored that the starting material was essentially reacted, filtered by suction to give a dark solution, and spin-dried to give C-22 as a dark oil (11.8g, 86% yield).
3) Weighing the intermediate C-22(12mmol), adding the ligand D-22(36mmol), adding 150mL of absolute ethanol into the system, stirring and reacting at 90 ℃ for 24 hours under the protection of nitrogen, and separating out a large amount of solid. TLC monitoring, the raw materials are basically reacted. And (5) carrying out suction filtration to obtain a crude product of the target product. Washed with petroleum ether and dried to give compound 22(7.8g, 70% yield).
HPLC purity is more than 99%.
Mass spectrum calculated 929.2; the test value was 929.1.
Example 3:
the preparation of compound 38, the synthetic route for which is as follows:
the preparation method comprises the following steps:
1) weighing A-38(60mmol), IrC1 under nitrogen protection system3·3H2O (25mmo1) is put into a reaction system, a mixed solution of 150mL of ethylene glycol ethyl ether and 70mL of purified water is added, nitrogen is used for protection, and the temperature is raised to 14 DEGThe reaction was stirred at 0 ℃ for 24 hours. The reaction was monitored by TLC and cooled to 30 ℃ until the starting material had reacted. Direct suction filtration gave a yellow solid which was washed first with 80mL ethanol and then with 120mL petroleum ether and dried under vacuum at 60 ℃ for 3 h to give intermediate B-38(10.7g, 70% yield).
2) Intermediate B-38(8mmol) was weighed, silver trifluoromethanesulfonate (24mmol) was added, 100mL of dichloromethane was added to the system, 40mL of isopropanol was added, and the reaction was carried out at room temperature for 24 hours under nitrogen. TLC monitored that the starting material was essentially reacted, filtered by suction to give a dark solution, and spin-dried to give C-38 as a dark oil (11.4g, 84% yield).
3) Weighing the intermediate C-38(12mmol), adding the ligand D-38(36mmol), adding 150mL of absolute ethanol into the system, stirring and reacting at 90 ℃ for 24 hours under the protection of nitrogen, and separating out a large amount of solid. TLC monitoring, the raw materials are basically reacted. And (5) carrying out suction filtration to obtain a crude product of the target product. Washed with about 50mL of petroleum ether and dried to give compound 38(7.7g, 63% yield).
HPLC purity is more than 99%.
Mass spectrum calculated 1014.24; the test value was 1013.69.
Example 4:
the synthetic route for the preparation of compound 50 is as follows:
the preparation method comprises the following steps:
1) weighing A-50(60mmol), IrC1 under nitrogen protection system3·3H2O (25mmo1) is put into a reaction system, a mixed solution of 150mL of ethylene glycol ethyl ether and 70mL of purified water is added, nitrogen is used for protection, and the temperature is raised to 140 ℃ to be stirred and reacted for 24 hours. The reaction was monitored by TLC and cooled to 30 ℃ until the starting material had reacted. Direct suction filtration gave a yellow solid which was washed first with 100mL ethanol and then with 100mL petroleum ether and dried under vacuum at 60 ℃ for 3 h to give intermediate B-50(12.7g, 72% yield).
2) Intermediate B-50(8mmol) was weighed, silver trifluoromethanesulfonate (24mmol) was added, 100mL of dichloromethane and 40mL of isopropyl alcohol were added to the system, and the reaction was carried out at room temperature for 24 hours under nitrogen atmosphere. TLC monitored that the starting material was essentially reacted, filtered by suction to give a dark solution, and spin-dried to give C-50 as a dark oil (13.3g, 88% yield).
3) Weighing intermediate C-50(12mmol), adding ligand D-50(36mmol), adding anhydrous ethanol 150mL, stirring at 90 deg.C under nitrogen protection, reacting for 24 hr, and separating out a large amount of solid. TLC monitoring, the raw materials are basically reacted. And (5) carrying out suction filtration to obtain a crude product of the target product. Washed with about 50mL of petroleum ether and dried to give compound 50(9.6g, 73% yield).
HPLC purity is more than 99%.
Mass spectrum calculated 1093.19; the test value was 1093.02.
Example 5:
preparation of compound 72, the synthetic route is as follows:
the preparation method comprises the following steps:
1) weighing A-72(60mmol), IrC1 under nitrogen protection system3·3H2O (25mmo1) is put into a reaction system, a mixed solution of 150mL of ethylene glycol ethyl ether and 70mL of purified water is added, nitrogen is used for protection, and the temperature is raised to 140 ℃ to be stirred and reacted for 24 hours. The reaction was monitored by TLC and cooled to 30 ℃ until the starting material had reacted. Directly filtering to obtain yellow solid, washing with ethanol 100mL, washing with petroleum ether 100mL, vacuum drying at 60 deg.C for 3 hr to obtain intermediate B-72(12.7g, yield 77%)
2) Adding the compound B-72(8mmol) into a three-neck flask, adding 200mL of ethylene glycol diethyl ether, sodium carbonate (6mmol) and the compound C-72(24mmol) into the three-neck flask, and stirring at room temperature for reacting for 24 hours; the reaction was monitored by TLC and after all the starting material had reacted, a yellow solid was obtained by suction filtration, purified with methanol and ethylene glycol ethyl ether and dried to give compound 72(12.8g, 69% yield).
HPLC purity is more than 99%.
Mass spectrum calculated 1164.37; the test value was 1164.29.
The compounds prepared in examples 6-15 below were synthesized in the same manner as in examples 1-6 listed above, and the mass spectra and molecular formulae are shown in Table 1.
TABLE 1 molecular formulas, calculated values by mass spectrometry and measured values by mass spectrometry of compounds prepared in examples 6-15
| Examples | Compound (I) | Molecular formula | Calculated mass spectrum | Mass spectrometric test values |
| 6 | 2 | C57H45D12IrN4O4 | 1066.48 | 1066.77 |
| 7 | 10 | C54H47IrN4O | 960.34 | 960.71 |
| 8 | 15 | C55H37IrN4OSe | 1042.18 | 1042.39 |
| 9 | 36 | C57H42IrN5O | 1005.30 | 1005.67 |
| 10 | 39 | C48H36IrN5OS | 923.23 | 923.45 |
| 11 | 42 | C50H33D6IrN6O | 938.32 | 938.41 |
| 12 | 43 | C47H37FIrN5O | 899.26 | 899.57 |
| 13 | 58 | C55H37FIrN7O | 1023.27 | 1023.68 |
| 14 | 62 | C49H45IrN4O4 | 946.31 | 946.66 |
| 15 | 67 | C55H41IrN4O4Se2 | 1174.11 | 1174.23 |
Example 16
An organic electroluminescent device was prepared using the organic phosphorus luminescent material (iridium metal complex) of compound 1 in example 1, and the specific process was as follows:
coating with a thickness of
The 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, the substrate was sequentially ultrasonically washed with solvents such as isopropyl alcohol, acetone, methanol, etc., dried, transferred to a plasma washer, washed for 5 minutes, and sent to a deposition machine.
The organic electroluminescent device is prepared by taking ITO as an anode, firstly evaporating N1- (2-naphthyl) -N4, N4-di (4- (2-naphthyl (phenyl) amino) phenyl) -N1-phenyl benzene-1, 4-diamine ('2-TNATA') 60nm on the ITO, and then evaporating NPB 60nm, a host substance 4, 4'-N, N' -biphenyl dicarbazole ('CBP') and a doping substance compound with the weight ratio of I-190: 10, mixing and evaporating 30nm, evaporating a hole blocking layer ('BALq') 10 nm), evaporating an electron transport layer ('Alq 3') 40nm, evaporating an electron injection layer LiF0.2nm and evaporating cathode Al 150 nm. The performance luminescence characteristics of the obtained device are tested by adopting a KEITHLEY2400 type source measuring unit and a CS-2000 spectral radiance luminance meter to evaluate the driving voltage, the service life and the luminescence efficiency. The results are shown in Table 1.
By substituting compound 1 with the compounds of examples 2 to 15, respectively, with reference to the above-mentioned methods, organic electroluminescent devices of the corresponding compounds were prepared. And testing the performance luminescence characteristics of the obtained device, wherein a KEITHLEY2400 type source measuring unit and a CS-2000 spectral radiance luminance meter are adopted for measurement so as to evaluate the driving voltage, the service life and the luminescence efficiency. The results are shown in Table 2.
Comparative example 1
An organic electroluminescent device was produced in the same manner as in example 6, except that the doped compound was replaced from compound 1 to the following compound:
the results of testing the organic electroluminescent devices prepared from the phosphorescent compounds of examples 1 to 15 and the organic electroluminescent device of comparative example 1 are shown in Table 2:
| compound (I) | Drive voltage (V) | Efficiency of | Life (h) | Colour(s) |
| Ir(ppy)3 | 1.0 | 1.0 | 1.0 | Green |
| 1 | 0.56 | 3.8 | 5.8 | Green |
| 2 | 0.56 | 3.2 | 5.1 | Green |
| 10 | 0.53 | 3.5 | 4.9 | Green |
| 15 | 0.56 | 3.6 | 5.1 | Green |
| 22 | 0.53 | 3.5 | 5.5 | Green |
| 36 | 0.51 | 3.7 | 5.0 | Green |
| 38 | 0.56 | 3.6 | 5.0 | Green |
| 39 | 0.52 | 3.5 | 4.8 | Green |
| 42 | 0.57 | 3.8 | 5.4 | Green |
| 43 | 0.53 | 3.2 | 5.2 | Green |
| 50 | 0.51 | 3.5 | 4.7 | Green |
| 58 | 0.56 | 3.6 | 4.5 | Green |
| 62 | 0.51 | 3.4 | 4.6 | Green |
| 67 | 0.50 | 3.9 | 4.3 | Green |
| 72 | 0.54 | 3.1 | 4.4 | Green |
Device test performance was referenced to device comparative example 1, and each performance index of comparative example 1 was set to 1.0. From the results of table 2, it can be seen that the phosphorescent compounds according to the present invention can be applied to OLED light emitting devices, and compared to comparative examples, the voltage, efficiency and lifetime are improved compared to known OLED materials.
The embodiments in the present description are described in a progressive manner, each embodiment focuses on differences from other embodiments, and the same and similar parts among the embodiments are referred to each other. The device disclosed by the embodiment corresponds to the method disclosed by the embodiment, so that the description is simple, and the relevant points can be referred to the method part for description.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (9)
1. A phosphorescent compound, characterized in that the structural general formula of the phosphorescent compound is:
wherein n is 1 or 2;
R1is at any position of the ring; r2Is at any position on ring Ar.
R1-R2As follows: any one of hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, sulfonic acid group, phosphoric acid group, boryl, C1-C20 alkyl, C6-C60 aryl, C3-C60 heteroaryl, C3-C60 cycloalkyl, C1-C60 alkoxy, C1-C60 alkylamino, C6-C60 arylamino, C6-C60 aryloxy, C6-C60 arylthio;
ar is a five-membered ring or a six-membered ring;
X1、X2are all O, S, N, Se, Si, NR1、NR2、CR1R2、Se、SiR1R2Any one of (a);
X3-6、X9-10all are any one or more of C, O, S, N, Se and Si;
X7、X8all are any one or more of C, O, S, N, Se and Si, and at least one of the N is contained;
the structural general formula of L is as follows:
wherein R is3At any position on ring Ar, R4Is at any position of the ring;
R3、R4are any one of hydrogen, deuterium, halogen, cyano, carboxyl, nitro, hydroxyl, sulfonic acid group, phosphoric acid group, boryl, C1-C20 alkyl, C6-C60 aryl, C3-C60 heteroaryl, C3-C60 cycloalkyl, C1-C60 alkoxy, C1-C60 alkylamino, C6-C60 arylamino, C6-C60 aryloxy and C6-C60 arylthio;
ar is a five-membered ring or a six-membered ring.
2. A phosphorescent compound according to claim 1 wherein R is1、R2Deuterium, fluorine atom, cyano, carboxyl, nitro, hydroxyl, sulfonic acid group, phosphoric acid group, boryl, C1-C10 alkyl, C6-C18 aryl, C3-C20 heteroaryl; wherein, the heteroaryl contains or does not contain any one or more of O, S, N, Se and Si.
3. The phosphorescent compound of claim 1, wherein R is1-R4Are all linked to adjacent substituents to form a monocyclic or polycyclic ring.
4. The phosphorescent compound as claimed in claim 1, wherein R in L1 is3、R4Deuterium, fluorine atom, alkyl, cyano, carboxyl, nitro, hydroxyl, sulfonic acid group, phosphoric acid group, borane group, C4-C10 aryl;
wherein, the aromatic ring contains or does not contain any one or more of O, S, N, Se and Si.
5. The phosphorescent compound as claimed in claim 1, wherein R in L2 is3、R4All deuterium, fluorine atom, cyano, carboxyl, nitro, hydroxyl, sulfonic acid group, phosphoric acid group, boryl, C1-C10 alkyl, C6-C18 aryl, and C3-C20 heteroaryl;
wherein, the heteroaryl in the C3-C20 heteroaryl contains or does not contain one or more of O, S, N, Se and Si.
6. A phosphorescent compound as claimed in claim 4 or claim 5 wherein the mono-or polycyclic ring is a C3-C30 aliphatic or aromatic ring.
7. A phosphorescent compound according to claim 4 or 5, wherein any of O, S, N, Se, Si is contained or not contained in the five-membered ring or the six-membered ring.
8. A preparation method of a phosphorescent compound, which is characterized in that the preparation method of the chemical formula I comprises the following steps:
when n is 1, the method comprises the following steps:
(1) under the protection of nitrogen, mixing the compound a with iridium trichloride trihydrate, and then adding the mixture into a mixed solvent of ethylene glycol ethyl ether and water for heating reaction to generate a bridging ligand b;
(2) mixing the bridging ligand b with silver trifluoromethanesulfonate, adding a mixed solvent of dichloromethane and isopropanol, and reacting at 15-30 ℃ for 16-30 hours to generate an intermediate product c;
(3) mixing the intermediate product c with the compound d, adding ethanol, and stirring to react at 90-110 ℃ for 16-30 hours to obtain a compound of a chemical formula I;
wherein the molar ratio of the compound a to the iridium trichloride trihydrate is 2-3: 1; the molar ratio of the bridging ligand b to the silver trifluoromethanesulfonate is 1: 2-5; the molar ratio of the intermediate product c to the compound d is 1: 1-2;
the synthetic route is as follows:
when n is 2, the method comprises the following steps:
1) under the protection of nitrogen, mixing the compound A and iridium trichloride trihydrate, and then adding the mixture into a mixed solvent of ethylene glycol ethyl ether and water for heating reaction to generate a bridging ligand B;
2) mixing the bridging ligand B and the compound C, and stirring for 16-30 hours under the protection of nitrogen at 15-30 ℃ to fully react to prepare a compound of a chemical formula II;
wherein the molar ratio of the compound A to the iridium trichloride trihydrate is 2-3:1, and the molar ratio of the bridging ligand B to the compound C is 1: 4-5;
the synthetic route is
9. Use of the phosphorescent compound according to claims 1 to 7 or the phosphorescent compound prepared by the method according to claim 8 in an organic electroluminescent device.
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| US20130328037A1 (en) * | 2011-02-16 | 2013-12-12 | Konica Minolta , Inc. | Organic electroluminescent element, lighting device, and display device |
| US20180026210A1 (en) * | 2016-07-19 | 2018-01-25 | Universal Display Corporation | Organic electroluminescent materials and devices |
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| US20080131730A1 (en) * | 2006-11-28 | 2008-06-05 | Canon Kabushiki Kaisha | Metal complex compound, electroluminescent device and display apparatus |
| CN103298907A (en) * | 2010-11-11 | 2013-09-11 | 环球展览公司 | Phosphorescent materials |
| US20130328037A1 (en) * | 2011-02-16 | 2013-12-12 | Konica Minolta , Inc. | Organic electroluminescent element, lighting device, and display device |
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