CN115594677A - A-D-A type organic compound and preparation method thereof - Google Patents
A-D-A type organic compound and preparation method thereof Download PDFInfo
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- CN115594677A CN115594677A CN202211115458.2A CN202211115458A CN115594677A CN 115594677 A CN115594677 A CN 115594677A CN 202211115458 A CN202211115458 A CN 202211115458A CN 115594677 A CN115594677 A CN 115594677A
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 239000000463 material Substances 0.000 claims abstract description 35
- 239000002994 raw material Substances 0.000 claims description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 239000007858 starting material Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical group [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- -1 4-tert-butylphenyl Chemical group 0.000 claims description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 5
- 229910052744 lithium Inorganic materials 0.000 claims description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052805 deuterium Inorganic materials 0.000 claims description 2
- DFENODSJEGDXHD-UHFFFAOYSA-N diphenylazaniumylideneazanide Chemical compound C=1C=CC=CC=1[N+](=[N-])C1=CC=CC=C1 DFENODSJEGDXHD-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000005580 one pot reaction 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
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 29
- 230000003111 delayed effect Effects 0.000 abstract description 6
- 238000007725 thermal activation Methods 0.000 abstract description 3
- 239000011368 organic material Substances 0.000 abstract description 2
- 230000003993 interaction Effects 0.000 abstract 1
- 230000008863 intramolecular interaction Effects 0.000 abstract 1
- 238000004020 luminiscence type Methods 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 150000001793 charged compounds Chemical class 0.000 description 6
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HJKGBRPNSJADMB-UHFFFAOYSA-N 3-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CN=C1 HJKGBRPNSJADMB-UHFFFAOYSA-N 0.000 description 2
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 2
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 238000001194 electroluminescence spectrum Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- KXERHVABNKZFON-UHFFFAOYSA-N 1-diphenylphosphoryldibenzofuran Chemical compound C1(=CC=CC=C1)P(=O)(C1=CC=CC=C1)C1=CC=CC=2OC3=C(C=21)C=CC=C3 KXERHVABNKZFON-UHFFFAOYSA-N 0.000 description 1
- AIAJGVRFXREWPK-UHFFFAOYSA-N 2,8-bis(diphenylphosphoryl)dibenzofuran Chemical compound C=1C=CC=CC=1P(C=1C=C2C3=CC(=CC=C3OC2=CC=1)P(=O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(=O)C1=CC=CC=C1 AIAJGVRFXREWPK-UHFFFAOYSA-N 0.000 description 1
- RKVIAZWOECXCCM-UHFFFAOYSA-N 2-carbazol-9-yl-n,n-diphenylaniline Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 RKVIAZWOECXCCM-UHFFFAOYSA-N 0.000 description 1
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 description 1
- NSXJEEMTGWMJPY-UHFFFAOYSA-N 9-[3-(3-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC(C=2C=CC=C(C=2)N2C3=CC=CC=C3C3=CC=CC=C32)=CC=C1 NSXJEEMTGWMJPY-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
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- C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings
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- C07D513/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains four or more hetero rings
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Abstract
The invention relates to an A-D-A type organic compound and a preparation method thereof, the material has the property of thermal activation delayed fluorescence, a single molecular structure presents a face-to-face receptor-donor-receptor (A-D-A) arrangement in space, the compound mainly has the function of realizing intramolecular interaction through space unconjugated connection, and double space interaction enables the material to have excellent luminescence property, and the material can be used as a material of an organic material layer of an organic luminescent device, in particular a luminescent material and/or a sensitizer.
Description
Technical Field
The invention relates to a luminescent material with an A-D-A type structure, application of the compound and an organic electroluminescent device adopting the compound.
Background
In order to improve the efficiency of the organic light emitting diode, various organic materials have been developed, such as conventional fluorescent materials, heavy metal-based phosphorescent materials, organic thermal activation delayed fluorescent materials, host materials, hole transport materials, electron transport materials, and the like. Fluorescent materials have good reliability but low efficiency. Phosphorescent materials are highly efficient, but require the use of heavy metals, which are expensive. The thermally activated delayed fluorescence material is not only high in efficiency, but also a pure organic compound, but the device efficiency roll-off is obvious, so that the application of the thermally activated delayed fluorescence material under high brightness is limited. It is important to develop new, efficient organic light emitting materials that can be used in the OLED field.
Disclosure of Invention
In order to solve the above technical problems, it is an object of the present invention to provide a thermally activated delayed fluorescence material having an a-D-a type, which can be used in an electroluminescent device. The invention relates to a novel luminescent material and a preparation method thereof, the luminescent material has the property of thermal activation delayed fluorescence, has excellent luminescent performance because a monomolecular structure is arranged face to face in space, can be used as a luminescent layer material of an organic electroluminescent device, can realize a luminescent device with high efficiency and low roll-off, and can bring huge application prospect and economic value.
The organic compound of A-D-A type of the present invention is represented by the following general formula:
in the formula: r 1 、R 2 、R 3 And R 4 Independently selected from one of the following groups: hydrogen, methyl, tert-butyl, cyclohexyl, phenyl, 4-tert-butylphenyl, diphenylamino, nitrogen-containing aromatic ring: (Such as carbazolyl groups, etc.); x 1 And/or X 2 Unsubstituted or, X 1 、X 2 Independently selected from single bond, double bond, O, S (= O) 2 CR 'R' or Se; x 1 And/or X 2 Unsubstituted means X 1 And/or X 2 Is absent; a is selected from C6-C60 arylamine or heteroaryl.
Further, in CR 'R', R 'and R' are selected from one of the following substituted or unsubstituted groups: C1-C10 alkyl, C6-C30 monocyclic aromatic hydrocarbon or polycyclic aromatic hydrocarbon, C5-C30 monocyclic hetero aromatic hydrocarbon or polycyclic hetero aromatic hydrocarbon. Preferably, the substituent is selected from one of deuterium, trifluoromethyl, cyano, halogen, C1-C10 alkyl or cycloalkyl, C6-C30 aryl, and C3-C30 heteroaryl.
The hetero atom in the present invention generally means an atom or an atomic group selected from N, O, S, P, si and Se, and preferably N, O and S.
The invention discloses a preparation method of the A-D-A type organic compound, which is obtained by reacting a first raw material with a second raw material; the reaction is carried out in the presence of a lithium reagent and an acid; the preferred lithium reagent is n-butyllithium; the acid is concentrated hydrochloric acid with the concentration of 30-37% and acetic acid; the reaction is a continuous one-pot method for ring closure reaction. Specifically, under the nitrogen atmosphere, a raw material I is subjected to a metallization reaction through a lithium compound, then a raw material II is added for a coupling reaction, and finally a ring-closing reaction is completed under an acidic condition.
The chemical structural formula of the raw material I is as follows:
the chemical structural formula of the raw material II is as follows:
in the first raw material and the second raw material, the substituent is the same as that of the A-D-A type organic compound, and Y is halogen such as Cl, br or I.
The compound of the general formula of the present invention may preferably be one of the following specific compounds, which are representative only:
the invention discloses application of the A-D-A type organic compound in preparing an organic electroluminescent device, in particular to application of the A-D-A type organic compound as a luminescent layer material, preferably as a luminescent dye and/or a sensitizer.
The OLED device prepared by the compound has low turn-on voltage, high luminous efficiency, high color purity and longer service life.
The preparation process of the compound is simple and feasible, the raw materials are easy to obtain, and the compound is suitable for mass production and amplification.
Drawings
FIG. 1 is a hydrogen spectrum of compound 2PXZ2TRZ prepared in accordance with the present invention;
FIG. 2 is a mass spectrum of Compound 2PXZ2TRZ prepared according to the example of the present invention;
FIG. 3 is a graph of device efficiency for device D1 prepared according to an embodiment of the present invention;
FIG. 4 is a graph showing an electroluminescence spectrum of a device D1 prepared in an example of the present invention.
Detailed Description
The specific production method of the above-mentioned novel compound of the present invention will be described in detail below by taking a plurality of synthesis examples as examples, but the production method of the present invention is not limited to these synthesis examples. All the raw materials of the invention are the existing products, and the specific preparation method and the testing method are the conventional technologies. The preparation of the organic compound of type A-D-A of the invention is schematically as follows:
EXAMPLE 2PXZ2TRZ Synthesis of Compounds
N-butyllithium (2.0 m,3.00 ml) was added dropwise to a tetrahydrofuran low temperature (-78 ℃) solution of the raw material A1 (1.00 g, 1.67 mmol) under a nitrogen atmosphere, after stirring at-78 ℃ for 1 hour, the raw material B1 (2.40 g, 4.92 mmol) dissolved in the tetrahydrofuran solution was added, followed by stirring at room temperature for 12 hours, the solvent was removed under reduced pressure, then acetic acid (40 ml) and hydrochloric acid (36%, 1 ml) were added, reaction was carried out at 120 ℃ for 15 hours, after completion of the reaction, the reaction liquid was poured into water and suction-filtered under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent dichloromethane: petroleum ether =1, v/v), to obtain a compound 2PXZ2 (1.26 g, yield: 55%), a white powder as a main product, MALDI-TOF-MS results: molecular ion peak 1378.797. FIG. 1 is a hydrogen spectrum of compound 2PXZ2 TRZ; figure 2 is a mass spectrum of compound 2PXZ2 TRZ. Also obtained was by-product 2PXZTRZ (0.35 g, yield: 21%), white powder, MALDI-TOF-MS result: molecular ion peak 988.945.
EXAMPLE 2Cz2TRZ Synthesis of Compounds
On the basis of example one, starting material A1 was replaced with starting material A2 (2.50 g, 5.13 mmol), and the other conditions were unchanged to give compound 2Cz2TRZ (1.18 g, yield: 50%) as a white powder. MALDI-TOF-MS results: molecular ion peak 1346.48.
EXAMPLE 2Cz2BO Synthesis of the Tri-Compounds
In addition to example two, the raw material B1 was replaced with the raw material B2 (2.20 g, 4.91 mmol), and the other conditions were not changed to obtain compound 2Cz2BO (1.18 g, yield: 53%) as a white powder. MALDI-TOF-MS results: molecular ion peak 1268.40.
Example 2Cz2BN Synthesis of the four Compounds
On the basis of example two, starting material B1 was replaced with starting material B3 (3.00 g, 5.04 mmol), and the other conditions were unchanged to give compound 2Cz2BN (1.37 g, yield: 50%) as a white powder. MALDI-TOF-MS results: molecular ion peak 1560.52.
Comparative example 2CzTRZ synthesis of compound
In addition to example two, the starting material A2 was replaced with the starting material A3 in an equivalent amount of substance without changing other conditions to obtain compound 2CzTRZ (0.85 g, yield: 55%) as a white powder. MALDI-TOF-MS results: molecular ion peak 877.32.
The invention discloses that the compound is used as a guest material to dope a host material as a luminescent layer, or is directly used as the luminescent layer for preparing an organic electroluminescent device; further, when the compound is used as a guest material and a host material is doped to jointly serve as a light-emitting layer, the doping concentration of the compound is 20 wt%. The doping concentration refers to the percentage of the guest material to the sum of the mass of the guest material and the mass of the host material.
Application examples
The organic electroluminescent device based on the compound has the specific structure as follows: indium Tin Oxide (ITO) is used as an anode, bis-pyrazino [2,3-f:2',3' -H ] quinoxaline-2, 3,6,7,10, 11-Hexanenitrile (HATCN) is used as a Hole Injection Layer (HIL), 4'- (cyclohexane-1, 1-diyl) bis (N, N-di-p-Tolylaniline) (TAPC) is used as a Hole Transport Layer (HTL), 4',4 ″ -tris (carbazol-9-yl) triphenylamine (TCTA) and 3,3 '-bis (9H-carbazol-9-yl) -1,1' -biphenyl (mCBP) are used as Electron Blocking Layers (EBL), the above compounds are used as guest materials to dope a2, 8-bis (diphenylphosphoryl) dibenzo [ B, D ] furan (PPF) host material together as a light emitting layer (EML), 2, 8-bis (diphenylphosphoryl) dibenzo [ B, D ] furan (PPF) is used as a Hole Blocking Layer (HBL), 4, 6-bis (3, 5-bis (3-phenylpyridine) -2, 1-yl) is used as a cathode (tml) to inject lithium octal); the specification of each layer of the organic electroluminescent device is as follows: ITO/HATCN (10 nm)/TAPC (40 nm)/TCTA (10 nm)/mCBP (8 nm)/PPF guest material (20 wt%) (20 nm)/PPF (8 nm) TmPyPB (40 nm)/Liq (3 nm)/Al (100 nm). The specific preparation process is conventional technology and adopts a vacuum evaporation method for preparation.
Specific performance data of organic electroluminescent devices based on the compounds prepared in the above examples are detailed in table 1, and a specific test method is the prior art.
The experimental data show that after the A-D-A type TADF material provided by the invention is applied to an organic electroluminescent device, the device has good performances of high luminous efficiency and low-efficiency roll-off, and simultaneously, the ultrahigh brightness of the electroluminescent device is realized. Therefore, the novel compound is an organic luminescent functional material with good performance, and is expected to be popularized and applied commercially. FIG. 3 is a device efficiency graph for device D1; FIG. 4 is a graph of the electroluminescence spectrum of the device D1.
Although the invention has been described in connection with the embodiments, the invention is not limited to the embodiments described above, and it is to be understood that various modifications and improvements may be made by those skilled in the art within the spirit of the invention, and all such modifications and improvements are intended to fall within the scope of the appended claims.
Claims (10)
1. An organic compound of type a-D-a, characterized in that the chemical structural formula of the organic compound of type a-D-a is as follows:
wherein: r is 1 、R 2 、R 3 And R 4 Independently selected from one of the following groups: hydrogen, methyl, tert-butyl, cyclohexane, phenyl, 4-tert-butylphenyl, diphenylamino, nitrogen-containing aromatic rings; x 1 And/or X 2 Unsubstituted or, X 1 、X 2 Independently selected from single bond, double bond, O, S (= O) 2 CR 'R' or Se; a is selected from C6-C60 arylamine or heteroaryl.
2. An organic compound of the type a-D-a according to claim 1, wherein in CR 'R ", R' and R" are independently selected from one of the following substituted or unsubstituted groups: C1-C10 alkyl, C6-C30 monocyclic aromatic hydrocarbon or polycyclic aromatic hydrocarbon, C5-C30 monocyclic hetero aromatic hydrocarbon or polycyclic hetero aromatic hydrocarbon.
3. The organic compound of type A-D-A as claimed in claim 2, wherein the substituent is selected from deuterium, trifluoromethyl, cyano, halogen, C1-C10 alkyl or cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl.
4. An organic compound of the type a-D-a according to claim 1, characterized in that it is as follows:
5. the process for the preparation of organic compounds of the type A-D-A according to claim 1, characterized in that they are obtained by reacting a first starting material with a second starting material; the chemical structural formula of the raw material I is as follows:
the chemical structural formula of the raw material II is as follows:
wherein the substituents are the same as those in claim 1, and Y is halogen.
6. The method for producing an organic compound of the type A-D-A according to claim 5, wherein the reaction is carried out in the presence of a lithium reagent or an acid.
7. The method for preparing an a-D-a type organic compound according to claim 6, wherein the lithium reagent is n-butyllithium; the acid is concentrated hydrochloric acid with the concentration of 30-37% and acetic acid; the reaction is a continuous one-pot method for ring closure reaction.
8. Use of an organic compound of the type A-D-A according to claim 1 for the preparation of an organic electroluminescent device.
9. Use of an organic compound of the type A-D-A as claimed in claim 1 as a light-emitting material.
10. Use of starting materials one and two for the preparation of organic compounds of type A-D-A according to claim 1.
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| CN113121442A (en) * | 2021-03-22 | 2021-07-16 | 深圳大学 | Synthesis method and application of spiro-substituted acridine compound |
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| CN113121442A (en) * | 2021-03-22 | 2021-07-16 | 深圳大学 | Synthesis method and application of spiro-substituted acridine compound |
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| LIU, HE: "Versatile Direct Cyclization Constructs Spiro-acridan Derivatives for Highly Efficient TADF emitters", ANGEWANDTE CHEMIE, INTERNATIONAL EDITION, vol. 60, no. 22 * |
| LIU, JUNYUAN: "Toward a BT.2020 green emitter through a combined multiple resonance effect and multi-lock strategy", NATURE COMMUNICATIONS, vol. 13, no. 1 * |
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