CN114853657A - Amide compound and preparation method thereof - Google Patents

Amide compound and preparation method thereof Download PDF

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CN114853657A
CN114853657A CN202210563305.8A CN202210563305A CN114853657A CN 114853657 A CN114853657 A CN 114853657A CN 202210563305 A CN202210563305 A CN 202210563305A CN 114853657 A CN114853657 A CN 114853657A
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amide compound
dosage
raw material
compound according
producing
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丁宗苍
陈佳
成春文
郭超
李帅
朱宇
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Jiangsu Nata Opto Electronic Material Co Ltd
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
    • C07C237/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to an acyclic carbon atom of a hydrocarbon radical substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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    • 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
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    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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  • Optics & Photonics (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

The invention provides an amide compound and a preparation method thereof, and the structural general formula is as follows:
Figure 343453DEST_PATH_IMAGE001
wherein R is an electron donating group; the preparation method comprises the following steps: adding raw materials A, B, CuI and alkali 1 into a reaction bottle, adding ultra-dry DMF (dimethyl formamide) and raw material C at 120 ℃ under the protection of N2Fully reacting to obtain an intermediate D; adding the intermediate D and the base 2 into a solvent of H2O, CH3OH and THF, and fully reacting at room temperature to obtain an intermediate E; acidifying the intermediate E to obtain an intermediate F; adding the intermediate F into anhydrous DMF, adding the raw materials G, HATU and DIEA, and fully reacting at room temperature to obtain an intermediate H; n is a radical of 2 And under protection, adding the intermediate H into anhydrous DCM, adding the raw material I at low temperature, and fully reacting at room temperature to obtain the amide compound which can be used as a light-emitting layer of an OLED and has high light-emitting efficiency.

Description

Amide compound and preparation method thereof
Technical Field
The invention relates to the technical field of organic photoelectric materials, in particular to a preparation method of an amide compound.
Background
The organic electroluminescent technology is a new generation display technology, and an organic electroluminescent diode (OLED) is light, thin and bendable in appearance and has the advantages of low cost, high luminous efficiency and capability of working at low temperature. Over the past few decades, this technology has achieved some success on the road of commercialization, such as smart phones, televisions, and in-vehicle displays. Organic electroluminescent materials are the core and foundation of electroluminescent devices, and therefore, new material development has great significance for continuous progress of electroluminescent technology.
TADF (thermally activated delayed fluorescence) is a new generation of luminescent material, and its luminescent quantum efficiency is theoretically as high as 100% as compared with conventional fluorescent and phosphorescent materials, and is a new luminescent material of great interest. The OLED (organic light-emitting diode) device prepared based on the material has the advantages of low cost and high luminous efficiency. The invention provides a D-A-D type amide compound which can be used as a luminescent layer material of an OLED.
Disclosure of Invention
The technical problem to be solved by the invention is as follows: in order to overcome the defects in the prior art, the invention provides a D-A-D type amide compound based on a TADF material and a preparation method thereof, wherein the amide compound can be used as a luminescent layer of an organic electroluminescent diode.
The technical scheme adopted for solving the technical problems is as follows: an amide compound represented by the general structural formula 1:
Figure 298528DEST_PATH_IMAGE001
wherein R is an electron donating group.
Preferably, the electron-donating group is carbazole, acridine, phenoxazine, or the like.
The amide compound represented by the above chemical formula 1 is preferably selected from any one of the following structures:
Figure 200100DEST_PATH_IMAGE002
the invention provides a preparation method of an amide compound, which specifically comprises the following steps:
step 1: mixing raw materials A, B, CuI and alkali 1 (anhydrous K) 2 PO 4 ) Adding into a reaction bottle, adding ultra-dry DMF (N, N-dimethylformamide) and the raw material C under the protection of N2, and fully reacting at 120 ℃ to obtain an intermediate D;
Figure 502906DEST_PATH_IMAGE003
step 2: intermediate D and base 2 were added to H 2 O、CH 3 OH and THF solvent are fully reacted at room temperature to obtain an intermediate E;
Figure 860069DEST_PATH_IMAGE004
and step 3: acidifying the intermediate E with acid to obtain an intermediate F;
Figure 539312DEST_PATH_IMAGE005
and 4, step 4: adding the intermediate F into anhydrous DMF, adding raw materials G, HATU (polypeptide condensation reagent, 2- (7-azobenzotriazole) -N, N, N ', N' -tetramethylurea hexafluorophosphate) and DIEA (N, N-diisopropylethylamine), and reacting at room temperature to obtain an intermediate H;
Figure 298320DEST_PATH_IMAGE006
and 5: in N 2 Under protection, adding the intermediate H into anhydrous DCM (dichloromethane), adding the raw material I at low temperature (liquid nitrogen and ethanol), and fully reacting at room temperature to obtain a product J;
Figure 772027DEST_PATH_IMAGE007
the product J is the prepared amide compound.
Preferably, the dosage of the raw material A in the step 1 is 1 eq; the dosage of the raw material B is 1.1 eq; the dosage of the raw material C is 0.4 eq; the dosage of the CuI is 0.4 eq; the amount of the base 1 used was 3 eq.
Preferably, the amount of the intermediate D in the step 2 is 1 eq; the amount of the base 2 used was 4 eq.
As a preferable scheme, the dosage of the raw material E in the step 3 is 1 eq; the amount of the acid used was 1.1 eq.
Preferably, the amount of the intermediate F in the step 4 is 1 eq; the dosage of the raw material G is 1.1 eq; the dosage of the HATU is 1.5 eq; the DIEA dosage is 5 eq.
Preferably, the amount of the intermediate H in the step 5 is 1 eq; the dosage of the raw material I is 6 eq.
Preferably, the low temperature in step 5 is achieved by using liquid nitrogen and alcohol.
The invention has the beneficial effects that: according to the amide compound and the preparation method thereof, the amide compound prepared based on the TADF material can be used as a light-emitting layer of an OLED and has high light-emitting efficiency.
Drawings
The invention is further illustrated by the following figures and examples.
FIG. 1: of intermediate D001 1 H NMR spectrum.
FIG. 2: LC-MS spectrum of intermediate F001.
FIG. 3: 1H NMR spectrum of intermediate H001.
FIG. 4: 1H NMR spectrum of J001.
FIG. 5: LC-MS spectrum of J001.
Detailed Description
The present invention will now be described in detail with reference to the accompanying drawings. This figure is a simplified schematic diagram, and merely illustrates the basic structure of the present invention in a schematic manner, and therefore it shows only the constitution related to the present invention.
The invention relates to an amide compound, which has a structural general formula shown as chemical formula 1:
Figure 616486DEST_PATH_IMAGE008
wherein R is an electron donating group.
Preferably, the electron-donating group is carbazole, acridine, phenoxazine, or the like.
The amide compound represented by the above chemical formula 1 is preferably selected from any one of the following structures:
Figure 568262DEST_PATH_IMAGE009
in this example, the preparation method of the amide compound having a structure of 001 is described in detail, and the amide compound prepared in this example is represented by J001, and the synthetic route of J001 is as follows:
Figure 447356DEST_PATH_IMAGE010
further comprising the steps of:
step 1: raw material A (1.9 mM,0.5 g), raw material B (2.09 mM, 0.35 g), CuI (0.76 mM, 0.14 g), and anhydrous K were weighed 2 PO 4 (5.7mM, 1.2g) and feedstock C (0.76 mM, 0.097 g), wherein K 2 PO 4 Is a base 1; mixing raw materials A, B, CuI and alkali 1 (anhydrous K) 2 PO 4 ) Adding into a three-mouth reaction bottle at N 2 Under protection, 20ml of ultra-dry DMF (N, N-dimethylformamide) and the raw material C were added, after a full reaction at 120 ℃ for 3 hours, water was added, filtration was carried out, the filtrate was extracted with EA/H2O to obtain an organic phase, dried over anhydrous MgSO4, filtered, the organic solvent was removed, and recrystallization was carried out with ethanol to obtain brown flocculent intermediate D001 (3g, yield: 53%). As shown in FIG. 1, of intermediate D001 1 H NMR spectrum, the abscissa represents concentration (unit: ppm).
Step 2: intermediate D001 (9.97 mM, 3 g) was added to a solution containing 15ml CH 3 OH, 15ml THF (tetrahydrofuran, C) 4 H 8 O) and 30ml of water, adding KOH (39.9 mM, 2.23 g) into the reaction solution, reacting for 3h at room temperature, and spin-drying the organic solvent to obtain an aqueous phase intermediate E001;
and step 3: dropwise adding HCl into the aqueous solution of the intermediate E001 while stirring until no precipitate is separated out, filtering, and drying to obtain a white intermediate F001(3g, yield: 100%);
the LC-MS spectrum of intermediate F001 is shown in fig. 2, wherein,
purity of LC: 99.57 percent
Mass spectrum: theoretical value: 287.09, found: 286.15[ M-H] - 。
And 4, step 4: intermediate F001 (10.5 mM, 3G), starting material G (11.6 mM, 1.4G), HATU (15.8 mM, 6G), DIEA (52.5 mM, 6.8G) were added to 30ml of anhydrous DMF, reacted at room temperature for 4H, and EA/H 2 O extraction to give an organic phase, drying, and column chromatography to give a white solid powder, intermediate H001 (3g, 73% yield), as shown in FIG. 3 for intermediate H001 1 H NMR spectrum.
And 5: in N 2 Intermediate H001 (1.28 mM,0.5 g) was added to 25ml of anhydrous DCM under protection, raw material I (7.68 mM, 1.9 g) was added at low temperature (liquid nitrogen and ethanol), reacted at room temperature for 4H, quenched with water, quenched with DCM/H 2 O extraction, drying the organic phase, spin-drying, and weighing with DCM/PECrystallization gave amide ligand J001 as an off-white powder (0.35 g, 72.9% yield);
as shown in FIG. 4 as J001 1 H NMR spectrum, FIG. 5 is LC-MS spectrum of J001, wherein,
purity of LC: 98.96 percent;
mass spectrum: theoretical value: 378.13 found: 379.28[ M + H] + 。
The synthesis of other compounds (002 and 003) is the same as in the above examples and is not repeated here.
In light of the foregoing description of preferred embodiments in accordance with the invention, it is intended that the appended claims be interpreted as including all such alterations and modifications as fall within the true spirit and scope of the invention. The technical scope of the present invention is not limited to the contents of the specification, and must be determined according to the scope of the claims.

Claims (10)

1. An amide compound characterized in that: the structural general formula of the amide compound is represented as the chemical formula:
Figure 316959DEST_PATH_IMAGE001
wherein R is an electron donating group.
2. The amide compound according to claim 1, wherein: the electron-donating group is one of carbazole, acridine and phenoxazine.
3. The amide compound according to claim 1, wherein: the amide compound is selected from any one of the following structures:
Figure 460496DEST_PATH_IMAGE002
Figure 718302DEST_PATH_IMAGE003
Figure 679304DEST_PATH_IMAGE004
。
4. a method for producing an amide compound, characterized in that: the method comprises the following steps:
step 1: adding the raw materials A, B, CuI and alkali 1 into a reaction bottle, adding ultra-dry DMF (dimethyl formamide) and the raw material C under the protection of N2, and fully reacting at 120 ℃ to obtain an intermediate D;
Figure 327455DEST_PATH_IMAGE005
step 2: intermediate D and base 2 were added to H 2 O、CH 3 OH and THF solvent are fully reacted at room temperature to obtain an intermediate E;
Figure 133737DEST_PATH_IMAGE006
and step 3: acidifying the intermediate E with acid to obtain an intermediate F;
Figure 198381DEST_PATH_IMAGE007
and 4, step 4: adding the intermediate F into anhydrous DMF, adding the raw materials G, HATU and DIEA, and fully reacting at room temperature to obtain an intermediate H;
Figure 64705DEST_PATH_IMAGE008
and 5: in N 2 Under protection, adding the intermediate H into anhydrous DCM, adding the raw material I at low temperature, and fully reacting at room temperature to obtain a product J;
Figure 200152DEST_PATH_IMAGE009
the product J is the prepared amide compound.
5. The process for producing an amide compound according to claim 4, wherein: in the step 1, the dosage of the raw material A is 1 eq; the dosage of the raw material B is 1.1 eq; the dosage of the raw material C is 0.4 eq; the dosage of the CuI is 0.4 eq; the amount of the base 1 used was 3 eq.
6. The process for producing an amide compound according to claim 4, wherein: the dosage of the intermediate D in the step 2 is 1 eq; the amount of the base 2 used was 4 eq.
7. The process for producing an amide compound according to claim 4, wherein: in the step 3, the dosage of the raw material E is 1 eq; the amount of the acid used was 1.1 eq.
8. The process for producing an amide compound according to claim 4, wherein: the dosage of the intermediate F in the step 4 is 1 eq; the dosage of the raw material G is 1.1 eq; the dosage of the HATU is 1.5 eq; the DIEA dosage is 5 eq.
9. The process for producing an amide compound according to claim 4, wherein: the dosage of the intermediate H in the step 5 is 1 eq; the dosage of the raw material I is 6 eq.
10. The process for producing an amide compound according to claim 4, wherein: and the low temperature in the step 5 is achieved by adopting liquid nitrogen and alcohol.
CN202210563305.8A 2022-05-20 2022-05-20 Amide compound and preparation method thereof Pending CN114853657A (en)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108164445A (en) * 2018-01-15 2018-06-15 华南理工大学 A kind of autonomous agent organic light emission small molecule material and its preparation method and application
JP2018159749A (en) * 2017-03-22 2018-10-11 東洋インキＳｃホールディングス株式会社 Red coloring composition for organic el display device, color filter for organic el display device, and organic el display device
CN112708134A (en) * 2020-12-28 2021-04-27 深圳瑞华泰薄膜科技股份有限公司 Colorless transparent copolyamide-imide film and preparation method thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2018159749A (en) * 2017-03-22 2018-10-11 東洋インキＳｃホールディングス株式会社 Red coloring composition for organic el display device, color filter for organic el display device, and organic el display device
CN108164445A (en) * 2018-01-15 2018-06-15 华南理工大学 A kind of autonomous agent organic light emission small molecule material and its preparation method and application
CN112708134A (en) * 2020-12-28 2021-04-27 深圳瑞华泰薄膜科技股份有限公司 Colorless transparent copolyamide-imide film and preparation method thereof

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