CN111253442A - 一种有机铱金属配合物、其制备方法及有机电致发光器件 - Google Patents
一种有机铱金属配合物、其制备方法及有机电致发光器件 Download PDFInfo
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- CN111253442A CN111253442A CN202010188803.XA CN202010188803A CN111253442A CN 111253442 A CN111253442 A CN 111253442A CN 202010188803 A CN202010188803 A CN 202010188803A CN 111253442 A CN111253442 A CN 111253442A
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- Prior art keywords
- metal complex
- iridium metal
- organic
- substituted
- organic iridium
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- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 65
- -1 iridium metal complex Chemical class 0.000 title claims abstract description 55
- 238000002360 preparation method Methods 0.000 title abstract description 18
- 239000003446 ligand Substances 0.000 claims abstract description 22
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims abstract description 5
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 239000000376 reactant Substances 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 claims description 6
- 239000012044 organic layer Substances 0.000 claims description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 6
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 230000001681 protective effect Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- AEDZKIACDBYJLQ-UHFFFAOYSA-N ethane-1,2-diol;hydrate Chemical compound O.OCCO AEDZKIACDBYJLQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 21
- 150000001875 compounds Chemical class 0.000 abstract description 8
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 11
- 238000005406 washing Methods 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 238000000967 suction filtration Methods 0.000 description 8
- 238000005303 weighing Methods 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 6
- 238000001819 mass spectrum Methods 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 239000008213 purified water Substances 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 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
- 238000004140 cleaning Methods 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 230000001376 precipitating effect Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound 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
- 238000005457 optimization Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007740 vapor deposition 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
- H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
有机铱金属配合物的结构式 | 分子式 | 质谱理论值 | 质谱测试值 |
L003 | C<sub>47</sub>H<sub>37</sub> F<sub>2</sub>IrN<sub>2</sub>O<sub>2</sub> | 892.04 | 892.06 |
L009 | C<sub>53</sub>H<sub>47</sub> IrN<sub>2</sub>O<sub>2</sub> | 936.33 | 936.30 |
L015 | C<sub>43</sub>H<sub>29</sub> F<sub>2</sub>IrN<sub>2</sub>O<sub>2</sub> | 836.18 | 836.20 |
L035 | C<sub>53</sub>H<sub>47</sub> IrN<sub>2</sub>O<sub>2</sub> | 936.33 | 936.30 |
L047 | C<sub>53</sub>H<sub>49</sub> IrN<sub>4</sub>O<sub>6</sub> | 1030.33 | 1030.30 |
L068 | C<sub>61</sub>H<sub>53</sub> D<sub>14</sub>IrN<sub>2</sub>O<sub>2</sub> | 1066.57 | 1066.60 |
Claims (10)
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Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111303213A (zh) * | 2020-04-15 | 2020-06-19 | 吉林奥来德光电材料股份有限公司 | 一种磷光铱配合物、其制备方法及有机电致发光器件 |
CN111690019A (zh) * | 2020-07-15 | 2020-09-22 | 奥来德(上海)光电材料科技有限公司 | 一种有机铱金属配合物及其制备方法与应用 |
CN112010908A (zh) * | 2020-08-31 | 2020-12-01 | 奥来德(上海)光电材料科技有限公司 | 一种用于红光电致发光材料的铱配合物及其制备方法和光电器件 |
EP3778614A1 (en) * | 2019-08-16 | 2021-02-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN112759617A (zh) * | 2021-01-06 | 2021-05-07 | 吉林奥来德光电材料股份有限公司 | 一种铱配合有机电致发光材料及其制备方法与应用 |
CN113214325A (zh) * | 2020-07-15 | 2021-08-06 | 奥来德(上海)光电材料科技有限公司 | 一种有机铱金属配合物及其制备方法和应用 |
CN113493482A (zh) * | 2020-04-01 | 2021-10-12 | 北京夏禾科技有限公司 | 含氰基取代的辅助配体的有机发光材料 |
CN113621000A (zh) * | 2021-08-25 | 2021-11-09 | 吉林奥来德光电材料股份有限公司 | 一种含有双齿配体的有机铱金属配合物及其应用 |
CN114075252A (zh) * | 2021-08-25 | 2022-02-22 | 吉林奥来德光电材料股份有限公司 | 铱金属化合物、发光材料、发光层和有机电致发光器件 |
CN115304644A (zh) * | 2021-05-07 | 2022-11-08 | 三星电子株式会社 | 有机金属化合物、包括其的有机发光器件、和包括所述有机发光器件的电子设备 |
WO2024142881A1 (ja) * | 2022-12-26 | 2024-07-04 | キヤノン株式会社 | 金属錯体及び有機発光素子 |
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CN113024610A (zh) * | 2019-12-24 | 2021-06-25 | 三星电子株式会社 | 有机金属化合物、包括其的有机发光器件和包括所述有机发光器件的电子设备 |
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2020
- 2020-03-17 CN CN202010188803.XA patent/CN111253442B/zh active Active
Patent Citations (2)
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US20100219407A1 (en) * | 2007-11-08 | 2010-09-02 | Canon Kabushiki Kaisha | Organic metal complex, and organic light emitting device and display apparatus using the same |
CN113024610A (zh) * | 2019-12-24 | 2021-06-25 | 三星电子株式会社 | 有机金属化合物、包括其的有机发光器件和包括所述有机发光器件的电子设备 |
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP3778614A1 (en) * | 2019-08-16 | 2021-02-17 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN113493482A (zh) * | 2020-04-01 | 2021-10-12 | 北京夏禾科技有限公司 | 含氰基取代的辅助配体的有机发光材料 |
CN111303213A (zh) * | 2020-04-15 | 2020-06-19 | 吉林奥来德光电材料股份有限公司 | 一种磷光铱配合物、其制备方法及有机电致发光器件 |
CN111690019A (zh) * | 2020-07-15 | 2020-09-22 | 奥来德(上海)光电材料科技有限公司 | 一种有机铱金属配合物及其制备方法与应用 |
CN113214325A (zh) * | 2020-07-15 | 2021-08-06 | 奥来德(上海)光电材料科技有限公司 | 一种有机铱金属配合物及其制备方法和应用 |
CN112010908A (zh) * | 2020-08-31 | 2020-12-01 | 奥来德(上海)光电材料科技有限公司 | 一种用于红光电致发光材料的铱配合物及其制备方法和光电器件 |
CN112010908B (zh) * | 2020-08-31 | 2023-03-24 | 奥来德(上海)光电材料科技有限公司 | 一种用于红光电致发光材料的铱配合物及其制备方法和光电器件 |
CN112759617A (zh) * | 2021-01-06 | 2021-05-07 | 吉林奥来德光电材料股份有限公司 | 一种铱配合有机电致发光材料及其制备方法与应用 |
CN112759617B (zh) * | 2021-01-06 | 2022-10-28 | 吉林奥来德光电材料股份有限公司 | 一种铱配合有机电致发光材料及其制备方法与应用 |
CN115304644A (zh) * | 2021-05-07 | 2022-11-08 | 三星电子株式会社 | 有机金属化合物、包括其的有机发光器件、和包括所述有机发光器件的电子设备 |
CN113621000A (zh) * | 2021-08-25 | 2021-11-09 | 吉林奥来德光电材料股份有限公司 | 一种含有双齿配体的有机铱金属配合物及其应用 |
CN114075252A (zh) * | 2021-08-25 | 2022-02-22 | 吉林奥来德光电材料股份有限公司 | 铱金属化合物、发光材料、发光层和有机电致发光器件 |
WO2024142881A1 (ja) * | 2022-12-26 | 2024-07-04 | キヤノン株式会社 | 金属錯体及び有機発光素子 |
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Inventor after: Wang Hui Inventor after: Li Jianxing Inventor after: Chen Ming Inventor after: Zhao He Inventor after: Li He Inventor after: Li Ming Inventor after: Jiang Zhiyuan Inventor after: Ma Xiaoyu Inventor before: Chen Ming Inventor before: Li Jianxing Inventor before: Zhao He Inventor before: Li He Inventor before: Li Ming Inventor before: Jiang Zhiyuan Inventor before: Ma Xiaoyu |
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