CN114437118A - Thienyl phenanthroline europium (III) complex material and preparation method and application thereof - Google Patents
Thienyl phenanthroline europium (III) complex material and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a thienyl phenanthroline europium (III) complex material and a preparation method and application thereof, wherein the material is a neutral phenanthroline ligand containing a thiophene group and a europium (III) complex material of beta-diketone derivative dibenzoylmethane, and has a structural formula shown in a formula (I). Synthesizing 1, 10-phenanthroline derivative ligand 3, 8-di (thiophene-2-yl) -1, 10-phenanthroline by adopting Suzuki coupling reaction, and synthesizing quaternary europium (III) complex Eu (DBM) by using beta-diketone derivative dibenzoyl methane as auxiliary ligand3PhenThi2. The complex introduces a thiophene group with a heteroatom S element, and explores the influence of the heteroatom on the light-emitting and charge-transporting performance of the organometallic complex. The device prepared by doping the material has the advantages of luminous efficiency, chemical stability and carrier mobilityHas excellent performances in the aspects of migration rate and the like.
Description
Technical Field
The invention belongs to the technical field of organic photoelectric materials, and particularly relates to a thienyl phenanthroline europium (III) complex material and a preparation method and application thereof.
Background
Since properties such as energy gap, solubility, electron affinity, stability in air, and the like of an organic semiconductor can be adjusted by changing its chemical composition, organic semiconductor materials are endowed with unparalleled flexibility in design compared to inorganic semiconductors. Organic electroluminescent devices have received much attention from researchers due to their potential applications in the field of flat panel displays. In recent decades, although conventional single-color light emitting devices have been advanced sufficiently, the development demand for high-purity full-color light emitting devices has not been satisfied.
To create a full color display, it is necessary to achieve pure blue, green and red emission. One way to solve this problem is to use organic europium (III) complexes in which the europium (III) ion acts as an emission center. Europium (iii) -based complexes exhibit strong visible light emission and their monochromaticity is independent of the external environment, so the spectral properties of europium (iii) ions are very suitable for full-color display devices. The electronic transition of the europium (III) internal 4f orbital gives it high purity red emission.
During the development of the OLED devices using europium (iii) complexes as the light-emitting material, considerable progress has been made in the relevant research. Ma et al (Fang, J.F.; You, H.; Gao, J.; Ma D.G.Chem.Phys.Lett.2004,392,11.) A high efficiency OLED was fabricated using tris (dibenzoylmethane) (3,4,7, 8-tetramethyl-1, 10-phenanthroline) europium (III) as the emitter, 4- (dicyanomethylene) -2-tert-butyl-6- (1,1,7, 7-tetramethylcinnarizyl-9-enyl) -4-hydropyran as the host matrix, with a maximum luminance at 20V of 2450cd/m2At 0.012mA/m2The lower luminance efficiency was 9.0 cd/A. Huang et al (Sun, M.; Xin, H.; Wang, K.Z.; Zhang, A.Y.; Jin, L.P.; Huang, C.H.chem.Commun.2003,702.) use tris (dibenzoylmethane) (2-4' -triphenylamino) imidazole [4, 5-f;, N.]1, 10-phenanthroline europium (III) as emission center, a luminance of 1305cd/m was obtained at 16V2A sharp red emission. Kido et al (Canzler, T.W.; Kido, J.org.Electron.2006,7,29.) selected tris (dibenzoyl formazan)Alkane) - (4, 7-biphenyl-1, 10-phenanthroline) europium (III) is used as a doping agent, N, N '-diphenyl-N, N' -bis (3-methylphenyl) -1, 1-biphenyl-4, 4-diamine is used as a main matrix, and the prepared OLED is at 0.02mA/m2With external quantum efficiencies as high as 7.5%. The excellent properties of these europium (III) complex materials are attributed to their europium (III) β -diketone complex structure, which has the advantages of a broad excitation band, high quantum yield and good color purity.
Disclosure of Invention
Aiming at the defects of the prior art, the invention provides a thienyl phenanthroline europium (III) complex material, a preparation method and application thereof, and the thienyl phenanthroline europium (III) complex material can be used as a luminescent material of a red light OLED device with high efficiency and high purity. The invention introduces thiophene group containing heteroatom S into neutral ligand of phenanthroline, and synthesizes europium (III) complex with beta-diketone derivative dibenzoyl methane as auxiliary ligand. The complex has potential application in organic electronic fields such as organic/polymer electroluminescent materials, organic integrated circuits, organic solar cells, organic field effect transistors, dye lasers, organic nonlinear optical materials, fluorescent probes and the like.
The invention is realized by the following technical scheme:
a thienyl phenanthroline europium (III) complex material is an europium (III) complex material of a neutral phenanthroline ligand containing a thienyl group and beta-diketone derivative dibenzoyl methane, and has a structural formula shown as a formula (I):
a preparation method of thienyl phenanthroline europium (III) complex material is shown as a reaction formula (II), and comprises the following steps:
step (i) preparation of precursor: reacting 3-thiopheneboronic acid with pinacol for 12 hours under an anaerobic condition to generate 3-thiopheneboronic acid pinacol ester;
step (ii) preparation of ligand: under the conditions of no oxygen, light protection and alkalinity, carrying out Suzuki coupling reaction on 3, 8-dibromo phenanthroline and excessive 3-thiophene boric acid pinacol ester prepared in the step (i), wherein a catalyst is tetrakis (triphenylphosphine) palladium, the reaction temperature is 115 ℃, and the reaction time is 28 hours, so as to synthesize 3, 8-bis (thiophene-2-yl) -1, 10-phenanthroline;
step (iii) preparation of europium (III) complex precursor: under the alkaline condition, carrying out the complex reaction of europium chloride hexahydrate and dibenzoyl methane, wherein the solvent is a mixed solvent of water and ethanol, the reaction temperature is 80 ℃, and the reaction time is 4h, thus obtaining Eu (DBM)3(H2O)2；
Step (iv) preparation of the final europium (III) complex: (iv) reacting the 3, 8-bis (thien-2-yl) -1, 10-phenanthroline obtained in step (ii) with Eu (DBM) obtained in step (iii) under anhydrous and oxygen-free conditions3(H2O)2Carrying out reaction at 115 ℃ for 1.5-2 h in toluene as a solvent to obtain the thienyl phenanthroline europium (III) complex Eu (DBM)3PhenThi2。
Preferably, the molar ratio of 3-thiopheneboronic acid to pinacol in step (i) is 1: 1.5.
Preferably, the molar ratio of the 3, 8-dibromophenanthroline to the 3-thiopheneboronic acid pinacol ester in step (ii) is 1: 2.2.
Preferably, the molar ratio of europium chloride hexahydrate to dibenzoylmethane in step (iii) is 1: 111.
Preferably, the 3, 8-bis (thien-2-yl) -1, 10-phenanthroline of step (iv) is reacted with Eu (DBM)3(H2O)2In a molar ratio of 1: 1.3.
The thienyl phenanthroline europium (III) complex material is applied to a red OLED material.
The invention has the following beneficial effects:
(1) the preparation method has the advantages of simple synthesis process, cheap raw materials and low cost.
(2) The invention introduces the thiophene group with heteroatom S element, and explores the influence of the heteroatom on the light-emitting and charge-transporting properties of the organometallic complex.
(3) The europium (III) complex not only expands the size of product molecules, but also enables the europium (III) complex to have strong ultraviolet-visible absorption and strong red fluorescence emission due to the existence of lanthanide europium (III) ions.
(4) The europium (III) complex has a strong red emission peak at 618nm, and is suitable for being used as a red OLED material.
Drawings
FIG. 1 is a scheme showing the reaction of 3-thiopheneboronic acid pinacol ester1HNMR spectrogram;
FIG. 2 shows Phenthi2Is1HNMR spectrogram;
FIG. 3 shows Phenthi2Ultraviolet-visible absorption spectrum of (a);
FIG. 4 shows Eu (DBM)3(H2O)2Ultraviolet-visible absorption spectrum of (a);
FIG. 5 shows Phenthi2Fluorescence emission spectrum of (a);
FIG. 6 shows Eu (DBM)3(H2O)2Fluorescence emission spectrum of (2);
FIG. 7 shows Eu (DBM)3PhenThi2Fluorescence emission spectrum of (1).
Detailed Description
In order to better understand the contents of the present invention patent, the technical scheme and route of the present invention will be further described by combining the drawings with specific experimental procedures. However, the following examples are not intended to limit the present invention.
Example 1
A thienyl phenanthroline europium (III) complex material is an europium (III) complex material of a neutral phenanthroline ligand containing a thienyl group and beta-diketone derivative dibenzoyl methane, and has a structural formula shown as a formula (I):
a thienyl phenanthroline europium (III) complex material has a reaction formula shown in a formula (II), and comprises the following specific steps:
(i) synthesis of 3-thiopheneboronic acid pinacol ester
Pinacol (1.385g, 11.722mmol) was dissolved in 20mL of toluene, the solution was degassed, slowly added to a reaction flask containing 3-thiopheneboronic acid (1g, 7.815mmol), and the reaction was carried out by heating to 115 ℃ under nitrogen atmosphere for 12 hours. After the reaction mixture was cooled to room temperature, it was extracted three times with dichloromethane, washed with water, and dried by adding anhydrous magnesium sulfate to the combined organic phases. Column chromatography on silica gel column using dichloromethane to petroleum ether 1:5 as eluent gave white solid powder (1.11g, 71.63% yield) which was 3-thiopheneboronic acid pinacol ester.
(ii) Synthesis of 3, 8-bis (thien-2-yl) -1, 10-phenanthroline (Phenthi)2)
3-thiophene boronic acid pinacol ester (0.683g, 3.254mmol), 3, 8-dibromo phenanthroline (0.5g, 1.489mmol), barium hydroxide octahydrate (0.791g, 2.507mmol) and tetrakis (triphenylphosphine) palladium were added to a reaction flask, a mixed solvent of degassed toluene (20mL), ethanol (2mL) and water (4mL) was added to the above mixed system, the reaction was completely protected from light, and the mixture was heated to 115 ℃ under a nitrogen atmosphere for 28 hours. The reaction mixture was cooled to room temperature, extracted three times with dichloromethane, washed with water, and dried by adding anhydrous magnesium sulfate to the combined organic phases. Column chromatography on silica gel column using ethyl acetate-petroleum ether-1: 10 as eluent gave a tan solid powder (0.318g, 62.57% yield), which was PhenThi2。
(iii) Synthesis of europium (III) Complex Eu (DBM)3(H2O)2
Europium chloride hexahydrate (1.832g, 5mmol) and dibenzoylmethane (3.364g, 15mmol) were charged to the reaction flask, and a mixed solution of degassed water (200mL) and ethanol (50mL) was added to the mixture. Will be provided withThe upper system was placed on a magnetic stirrer at room temperature and stirred, and an aqueous potassium carbonate solution (2.07g/10mL) was slowly added through a syringe and reacted for 4h under a nitrogen atmosphere. The resulting reaction mixture was filtered using a suction filter funnel and washed with water, and the resulting crude product was dried in a vacuum oven at room temperature. The dried crude product was dissolved in 200mL of hot ethanol, filtered while hot, and 100mL of water was added to the filtrate after cooling to room temperature to precipitate a yellow solid, which was further recrystallized in a refrigerator at-20 ℃. After filtering the product and drying in vacuo at room temperature, cyclohexane (20mL of cyclohexane per gram of crude) was added and stirred to remove excess dibenzoylmethane. Vacuum filtering to obtain product, and drying at room temperature in vacuum drying oven to obtain yellow solid (2.767g, yield 62.46%), which is Eu (DBM)3(H2O)2。
(iv) Synthesis of europium (III) Complex Eu (DBM)3PhenThi2
Eu (DBM)3(H2O)2(0.125g, 0.145mmol) and PhenThi2(0.05g, 0.145mmol) was added to a reaction flask, degassed toluene (5mL) was added, and the mixture was heated to 115 ℃ under a nitrogen atmosphere for 1.5 to 2 hours. Filtering the obtained clear yellow brown solution, putting the filtrate cooled to room temperature into a refrigerator at the temperature of-20 ℃ for recrystallization to obtain yellow brown crystals (0.058g, the yield is 34.21 percent), namely the thienyl phenanthroline europium (III) complex Eu (DBM)3PhenThi2。
Example 2 europium (III) Complex Eu (DBM)3PhenThi2Summary of physical Properties of intermediate products thereof
In this example, the structures of the precursor and the ligand are characterized by a nuclear magnetic resonance spectrometer (NMR), and the spectral properties of the ligand, the europium (iii) complex precursor, and the europium (iii) complex are determined by analysis with an ultraviolet-visible spectrophotometer (LAMBDA-35) and a fluorescence spectrophotometer (RF-6000), specifically including the following steps:
(1) weighing 3-thiophene pinacol borate (5mg), dissolving in deuterium-depleted chloroform (0.6mL), and analyzing and testing by a nuclear magnetic resonance spectrometer (NMR) to obtain the 3-thiophene pinacol borate1HNMR spectrogram, test resultAs shown in fig. 1.
As can be seen from FIG. 1, the peak at 1.27ppm corresponds to the four methyl groups of 3-thiopheneboronic acid pinacol ester, and the peaks at 7.19, 7.27 and 7.33ppm correspond to the three active hydrogens in the thienyl group of 3-thiopheneboronic acid pinacol ester, respectively, thus deducing that the compound is 3-thiopheneboronic acid pinacol ester.
(2) Weighing Phenthi2(5mg) dissolved in deuterium-charged chloroform (0.6mL) and analyzed by nuclear magnetic resonance spectrometer (NMR) to give PhenThi2Is/are as follows1The HNMR spectrogram and the test result are shown in figure 2.
As can be seen from FIG. 2, the peaks at 7.54, 7.61 and 7.78ppm correspond to PhenThi2The peaks at 7.88, 8.14 and 9.49 correspond to PhenThi2Three active hydrogens in the thienyl group of (A), thereby deducing that the compound is PhenThi2。
(3) Weighing Phenthi2(1mg) was dissolved in methylene chloride and prepared to have a concentration of 1X 10-5The mol/L solution is analyzed and tested by an ultraviolet-visible spectrophotometer (LAMBDA-35) to obtain Phenthi2The test results are shown in fig. 3.
As can be seen from FIG. 3, Phenthi2The maximum absorption peak of (2) is located at 332nm, wherein the absorption peak at 278nm is caused by the stronger absorption capacity of the phenanthroline group.
(4) Weighing Eu (DBM)3(H2O)2(1mg) was dissolved in methylene chloride and prepared to have a concentration of 1X 10-5The mol/L solution is analyzed and tested by an ultraviolet-visible spectrophotometer (LAMBDA-35) to obtain Eu (DBM)3(H2O)2The test results are shown in fig. 4.
As shown in FIG. 4, Eu (DBM)3(H2O)2The maximum absorption peak of (2) is located at 347 nm.
(5) Weighing Phenthi2(1mg) was dissolved in methylene chloride and prepared to have a concentration of 1X 10-5The solution of mol/L is analyzed and tested by a fluorescence spectrophotometer (RF-6000) to obtain PhenThi2Fluorescent emission of (2)The spectra, the test results are shown in fig. 5.
As can be seen from FIG. 5, Phenthi2The maximum emission peak of the compound is at 395nm, and the introduction of the thiophene group causes the emission wavelength to show obvious red shift.
(6) Weighing Eu (DBM)3(H2O)2(1mg) was dissolved in methylene chloride and prepared to have a concentration of 1X 10-5The mol/L solution is analyzed and tested by a fluorescence spectrophotometer (RF-6000) to obtain Eu (DBM)3(H2O)2The fluorescence emission spectrum of (2) and the test results are shown in FIG. 6.
As shown in FIG. 6, Eu (DBM)3(H2O)2The maximum emission peak of (a) is located at 619nm, so that a narrow emission peak of high wavelength corresponds to the properties of the europium (III) complex.
(7) Weighing Eu (DBM)3PhenThi2(1mg) was dissolved in methylene chloride and prepared to have a concentration of 1X 10-5The mol/L solution is analyzed and tested by a fluorescence spectrophotometer (RF-6000) to obtain Eu (DBM)3PhenThi2The fluorescence emission spectrum of (2) and the test results are shown in FIG. 7.
As can be seen from FIG. 7, Eu (DBM)3PhenThi2Is located at 618nm, wherein the eu (iii) ion has a greater influence on the maximum emission wavelength of the compound than other groups.
In conclusion, the europium (III) complex Eu (DBM)3PhenThi2Due to the existence of lanthanide europium (III) ion, the size of product molecule is expanded, and Eu (DBM)3PhenThi2Has strong ultraviolet-visible absorption and strong red fluorescence emission. In particular Eu (DBM)3PhenThi2Has an intense red emission peak at 618nm and has potential as a red OLED material.
While the invention has been shown and described with reference to certain preferred embodiments thereof, it will be understood by those skilled in the art that the foregoing is a more detailed description of the invention, taken in conjunction with the specific embodiments thereof, and that no limitation of the invention is intended thereby. Various changes in form and detail, including simple deductions or substitutions, may be made by those skilled in the art without departing from the spirit and scope of the invention.
Claims (7)
1. The thienyl phenanthroline europium (III) complex material is characterized in that the material is a neutral phenanthroline ligand containing a thiophene group and a europium (III) complex material of beta-diketone derivative dibenzoylmethane, and has a structural formula shown as a formula (I):
2. the method for preparing the thienylphenanthroline europium (III) complex material in claim 1, wherein the reaction formula is shown as a formula (II), and the method comprises the following steps:
step (i) preparation of precursor: reacting 3-thiopheneboronic acid with pinacol for 12 hours under an anaerobic condition to generate 3-thiopheneboronic acid pinacol ester;
step (ii) preparation of the ligand: under the conditions of no oxygen, light protection and alkalinity, carrying out Suzuki coupling reaction on 3, 8-dibromophenanthroline and excessive 3-thiophene boric acid pinacol ester prepared in the step (i), wherein a catalyst is tetrakis (triphenylphosphine) palladium, the reaction temperature is 115 ℃, and the reaction time is 28h, so as to synthesize 3, 8-di (thiophene-2-yl) -1, 10-phenanthroline;
step (iii) preparation of europium (III) complex precursor: under the alkaline condition, carrying out the complex reaction of europium chloride hexahydrate and dibenzoyl methane, wherein the solvent is a mixed solvent of water and ethanol, the reaction temperature is 80 ℃, and the reaction time is 4h, thus obtaining Eu (DBM)3(H2O)2；
Step (iv) preparation of the final europium (III) complex: (iii) reacting the product of step (ii) under anhydrous and anaerobic conditions3, 8-bis (thien-2-yl) -1, 10-phenanthroline and Eu (DBM) obtained in step (iii)3(H2O)2Carrying out reaction at 115 ℃ for 1.5-2 h in toluene as a solvent to obtain the thienyl phenanthroline europium (III) complex Eu (DBM)3PhenThi2。
3. The method for preparing the thienylphenanthroline europium (III) complex material according to claim 2, wherein the molar ratio of the 3-thiopheneboronic acid to the pinacol in step (i) is 1: 1.5.
4. The method for preparing the thienylphenanthroline europium (III) complex material according to claim 2, wherein the molar ratio of the 3, 8-dibromophenanthroline to the 3-thiopheneboronic acid pinacol ester in the step (ii) is 1: 2.2.
5. The method for preparing the thienylphenanthroline europium (III) complex material according to claim 2, wherein the molar ratio of the europium chloride hexahydrate and dibenzoylmethane in step (iii) is 1: 111.
6. The method according to claim 2, wherein the 3, 8-bis (thien-2-yl) -1, 10-phenanthroline and Eu (DBM) in step (iv)3(H2O)2In a molar ratio of 1: 1.3.
7. The use of the thienylphenanthroline europium (III) complex material as claimed in claim 1 as a red-light OLED material.
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