CN115594677B - A-D-A type organic compound and preparation method thereof - Google Patents

A-D-A type organic compound and preparation method thereof Download PDF

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CN115594677B
CN115594677B CN202211115458.2A CN202211115458A CN115594677B CN 115594677 B CN115594677 B CN 115594677B CN 202211115458 A CN202211115458 A CN 202211115458A CN 115594677 B CN115594677 B CN 115594677B
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CN115594677A (en
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唐建新
谢凤鸣
李昊泽
李艳青
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Abstract

The invention relates to an A-D-A type organic compound and a preparation method thereof, the material has a thermal activation delayed fluorescence property, 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 intermolecular interaction through space non-conjugated connection, and the material has excellent luminescence performance due to double space interaction, and 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

A-D-A type organic compound and preparation method thereof
Technical Field
The invention relates to a luminescent material with an A-D-A type structure, and also relates to 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 heat-activated delayed fluorescent materials, host materials, hole transport materials, electron transport materials, and the like. The fluorescent material has good reliability but low efficiency. Phosphorescent materials are highly efficient, but require heavy metals and are expensive. The thermally activated delayed fluorescence material is not only efficient, but also a pure organic compound, but the device efficiency roll-off is obvious, limiting its application under high brightness. It is important to develop new, efficient organic luminescent materials that can be used in the field of OLEDs.
Disclosure of Invention
In order to solve the technical problems, the invention aims to provide a heat-activated delayed fluorescence material with A-D-A type, which can be used for electroluminescent devices. The invention relates to a novel luminescent material and a preparation method thereof, wherein the luminescent material has a thermal activation delayed fluorescence property, a single molecular structure is arranged face to face in space, and the luminescent material has excellent luminescence property, can be used as a luminescent layer material of an organic electroluminescent device, and can realize a luminescent device with high efficiency and low roll-off, so that the luminescent material can bring great application prospect and economic value.
The A-D-A type organic compound of the present invention is represented by the following general formula:
wherein: r is R 1 、R 2 、R 3 And R is 4 Independently selected from one of the following groups: hydrogen, methyl, t-butyl, cyclohexenyl, phenyl, 4-t-butylphenyl, diphenylamino, nitrogen-containing aromatic rings (e.g., carbazolyl, etc.); x is X 1 And/or X 2 Unsubstituted or, X 1 、X 2 Independently selected from single bond, double bond, O, S, S (=o) 2 CR 'R' or Se; x is X 1 And/or X 2 Unsubstituted means X 1 And/or X 2 Absence of; a is selected from aromatic amine or heteroaryl of C6-C60.
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 heteroaromatic hydrocarbon or polycyclic heteroaromatic hydrocarbon. Preferably, the substituent is selected from one of deuterium, trifluoromethyl, cyano, halogen, C1-C10 alkyl or cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl.
Heteroatoms in the present invention generally refer to atoms or groups of atoms selected from N, O, S, P, si and Se, preferably N, O and S.
The invention discloses a preparation method of the A-D-A 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, an acid; a 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, the first raw material is subjected to a metallization reaction by a lithium compound in a nitrogen atmosphere, then the second raw material is added for a coupling reaction, and finally the ring closure 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 and second raw materials, the substituent is the same as the substituent of the above-mentioned A-D-A type organic compound, and Y is halogen such as Cl, br or I.
The compounds of the general formula according to the invention may preferably be one of the following specific compounds, which are only representative:
the invention discloses application of the A-D-A type organic compound in preparation of an organic electroluminescent device, and specifically, the A-D-A type organic compound is used as a luminescent layer material, preferably as a luminescent dye and/or sensitizer.
The OLED device prepared by the compound has low starting voltage, high luminous efficiency, high color purity and longer service life.
The preparation process of the compound is simple and feasible, 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 the example of the present invention;
FIG. 2 is a mass spectrum of compound 2PXZ2TRZ prepared in the example of the present invention;
FIG. 3 is a device efficiency diagram of device D1 prepared in accordance with an embodiment of the present invention;
FIG. 4 is an electroluminescent spectrum of a device D1 according to an embodiment of the present invention.
Detailed Description
Specific methods for preparing the above novel compounds of the present invention will be described below by way of example with reference to a plurality of synthesis examples, but the preparation method of the present invention is not limited to these synthesis examples. All raw materials of the invention are existing products, and the specific preparation method and the testing method are conventional technologies. The preparation of the A-D-A organic compound of the invention is schematically shown below:
example 2PXZ2TRZ Synthesis of Compound
N-butyllithium (2.0 m,3.00 ml) was added dropwise to a tetrahydrofuran low temperature (-78 ℃) solution of raw material A1 (1.00 g, 1.67 mmol) under nitrogen atmosphere, after stirring for 1 hour at-78 ℃, raw material B1 (2.40 g, 4.92 mmol) dissolved in tetrahydrofuran solution was added, then stirring for 12 hours at room temperature, the solvent was removed under reduced pressure, acetic acid (40 ml) and hydrochloric acid (36%, 1 ml) were then added, reaction was carried out for 15 hours at 120 ℃, after the completion of the reaction, the reaction solution was poured into water and suction filtered under reduced pressure, and the filter residue was purified by silica gel column chromatography (developing solvent dichloromethane: petroleum ether=1:1, v/v) to obtain compound 2PXZ2TRZ (1.26 g, yield: 55%) as a white powder as a main product, MALDI-TOF-MS result: molecular ion peak 1378.797. FIG. 1 is a hydrogen spectrum of Compound 2PXZ2 TRZ; fig. 2 is a mass spectrum of compound 2PXZ, 2 TRZ. Byproduct 2PXZTRZ (0.35 g, yield: 21%) was also obtained as a white powder, MALDI-TOF-MS results: 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), the other conditions being unchanged, to give compound 2Cz2TRZ (1.18 g, yield: 50%) as a white powder. MALDI-TOF-MS results: molecular ion peak 1346.48.
Example three 2Cz2BO synthesis of compounds
On the basis of example two, starting material B1 was replaced by starting material B2 (2.20 g, 4.91 mmol), the other conditions being unchanged, compound 2Cz2BO (1.18 g, yield: 53%) was obtained as a white powder. MALDI-TOF-MS results: molecular ion peak 1268.40.
Example four 2Cz2BN synthesis of compounds
On the basis of example two, starting material B1 was replaced by starting material B3 (3.00 g, 5.04 mmol), the other conditions being unchanged, compound 2Cz2BN (1.37 g, yield: 50%) was obtained as a white powder. MALDI-TOF-MS results: molecular ion peak 1560.52.
2CzTRZ Synthesis of comparative example one Compound
On the basis of example two, starting material A2 was replaced with starting material A3 in an equal amount, the other conditions being unchanged, to give compound 2CzTRZ (0.85 g, yield: 55%) as a white powder. MALDI-TOF-MS results: molecular ion peak 877.32.
The invention discloses a method for preparing an organic electroluminescent device by using the compound as a guest material doped with a host material as a luminescent layer or directly as the luminescent layer; further, when the above-mentioned compounds are used as guest materials and doped with host materials together as light-emitting layers, the doping concentration of the compounds is 20 wt%. Doping concentration refers to the percentage of guest material relative to the sum of the mass of guest material and 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, bipyrazino [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' -tris (carbazol-9-yl) triphenylamine (TCTA) and 3,3 '-bis (9H-carbazol-9-yl) -1,1' -biphenyl (mCBP) is used as an Electron Blocking Layer (EBL), the above compounds are used as guest materials doped with 2, 8-bis (diphenylphosphoryl) dibenzo [ B, D ] furan (PPF) host materials together as a light emitting layer (EML), 2, 8-bis (diphenylphosphoryl) dibenzo [ B, D ] furan (PPF) is used as a hole blocking layer (HTL), 4, 6-bis (carbazol-9-yl) triphenylamine (TCTA) and 3,3 '-bis (9H-carbazol-9-yl) -1,1' -biphenyl (mCBP) is used as an Electron Blocking Layer (EBL), the above compounds are used as guest materials doped 2, 8-bis (diphenylphosphoryl) dibenzo [ B, D ] furan (PPF) and (PPF) is used as a hole blocking layer (Pl) and as electron blocking layer (E-layer (E); 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 the organic electroluminescent devices based on the compounds prepared in the above examples are shown in table 1, and specific test methods are 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 meanwhile, the ultra-high brightness of the electroluminescent device is realized. Therefore, the novel compound is an organic luminous functional material with good performance, and is expected to be popularized and applied commercially. FIG. 3 is a device efficiency diagram of device D1; FIG. 4 is an electroluminescence spectrum of the device D1.
While the present invention has been described in connection with the embodiments, it is not limited to the above embodiments, but it should be understood that various modifications and improvements can be made by those skilled in the art under the guidance of the inventive concept, and all such modifications and improvements should fall within the scope of the appended claims.

Claims (3)

1. An a-D-a type organic compound characterized by having the chemical structural formula:
；
；
；
。
2. use of an organic compound of the type a-D-a according to claim 1 for the preparation of an organic electroluminescent device.
3. Use of an organic compound of the type a-D-a according to claim 1 as a luminescent material.
CN202211115458.2A 2022-09-14 2022-09-14 A-D-A type organic compound and preparation method thereof Active CN115594677B (en)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021008374A1 (en) * 2019-07-18 2021-01-21 清华大学 Novel compound and application thereof, and organic electroluminescent device using same
CN113121442A (en) * 2021-03-22 2021-07-16 深圳大学 Synthesis method and application of spiro-substituted acridine compound

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021008374A1 (en) * 2019-07-18 2021-01-21 清华大学 Novel compound and application thereof, and organic electroluminescent device using same
CN113121442A (en) * 2021-03-22 2021-07-16 深圳大学 Synthesis method and application of spiro-substituted acridine compound

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
Liu, He.Versatile Direct Cyclization Constructs Spiro-acridan Derivatives for Highly Efficient TADF emitters.Angewandte Chemie, International Edition.2021,第60卷(第22期),全文. *
Liu, Junyuan.Toward a BT.2020 green emitter through a combined multiple resonance effect and multi-lock strategy.Nature Communications.2022,第13卷(第1期),全文. *

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