CN114773273A - Phenanthroimidazole-based organic blue light micromolecule and application thereof in preparation of non-doped organic electroluminescent device - Google Patents
Phenanthroimidazole-based organic blue light micromolecule and application thereof in preparation of non-doped organic electroluminescent device Download PDFInfo
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- CN114773273A CN114773273A CN202210517122.2A CN202210517122A CN114773273A CN 114773273 A CN114773273 A CN 114773273A CN 202210517122 A CN202210517122 A CN 202210517122A CN 114773273 A CN114773273 A CN 114773273A
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- GZPPANJXLZUWHT-UHFFFAOYSA-N 1h-naphtho[2,1-e]benzimidazole Chemical compound C1=CC2=CC=CC=C2C2=C1C(N=CN1)=C1C=C2 GZPPANJXLZUWHT-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims description 23
- 239000000463 material Substances 0.000 claims abstract description 34
- 125000001424 substituent group Chemical group 0.000 claims abstract description 3
- -1 cyano-substituted phenyl Chemical group 0.000 claims description 7
- 238000002347 injection Methods 0.000 claims description 6
- 239000007924 injection Substances 0.000 claims description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 230000005525 hole transport Effects 0.000 claims description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 2
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- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims 1
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- 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 3
- 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 3
- YYVYAPXYZVYDHN-UHFFFAOYSA-N 9,10-phenanthroquinone Chemical compound C1=CC=C2C(=O)C(=O)C3=CC=CC=C3C2=C1 YYVYAPXYZVYDHN-UHFFFAOYSA-N 0.000 description 3
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- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- UNXISIRQWPTTSN-UHFFFAOYSA-N boron;2,3-dimethylbutane-2,3-diol Chemical compound [B].[B].CC(C)(O)C(C)(C)O UNXISIRQWPTTSN-UHFFFAOYSA-N 0.000 description 2
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- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 2
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- NNEOYCMCJMLRSD-UHFFFAOYSA-N 1-benzyl-4-bromobenzene Chemical compound C1=CC(Br)=CC=C1CC1=CC=CC=C1 NNEOYCMCJMLRSD-UHFFFAOYSA-N 0.000 description 1
- JHLKSIOJYMGSMB-UHFFFAOYSA-N 1-bromo-3,5-difluorobenzene Chemical compound FC1=CC(F)=CC(Br)=C1 JHLKSIOJYMGSMB-UHFFFAOYSA-N 0.000 description 1
- USYQKCQEVBFJRP-UHFFFAOYSA-N 1-bromo-3-phenylbenzene Chemical group BrC1=CC=CC(C=2C=CC=CC=2)=C1 USYQKCQEVBFJRP-UHFFFAOYSA-N 0.000 description 1
- XLQSXGGDTHANLN-UHFFFAOYSA-N 1-bromo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(Br)C=C1 XLQSXGGDTHANLN-UHFFFAOYSA-N 0.000 description 1
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 1
- ONCCVJKFWKAZAE-UHFFFAOYSA-N 2-bromo-9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=C(Br)C=C12 ONCCVJKFWKAZAE-UHFFFAOYSA-N 0.000 description 1
- MBHPOBSZPYEADG-UHFFFAOYSA-N 2-bromo-9,9-dimethylfluorene Chemical compound C1=C(Br)C=C2C(C)(C)C3=CC=CC=C3C2=C1 MBHPOBSZPYEADG-UHFFFAOYSA-N 0.000 description 1
- WNXNWOBGPRKOJF-UHFFFAOYSA-N 2-bromo-9,9-diphenylfluorene Chemical compound C12=CC(Br)=CC=C2C2=CC=CC=C2C1(C=1C=CC=CC=1)C1=CC=CC=C1 WNXNWOBGPRKOJF-UHFFFAOYSA-N 0.000 description 1
- ZLDMZIXUGCGKMB-UHFFFAOYSA-N 3,5-dibromobenzaldehyde Chemical compound BrC1=CC(Br)=CC(C=O)=C1 ZLDMZIXUGCGKMB-UHFFFAOYSA-N 0.000 description 1
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- 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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- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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Abstract
A phenanthroimidazole-based organic blue light micromolecule and application thereof in preparing a non-doped organic electroluminescent device belong to the technical field of organic photoelectric materials. According to the invention, the phenanthroimidazole with the rigid structure is connected with the neutral group or the weak receptor group in a reasonable manner, so that the excited state of the molecule has the characteristic of a weak charge transfer state, and the improvement of the color purity of blue light emission is facilitated. Meanwhile, a substituent group introduced on the phenanthroimidazole has certain steric hindrance to inhibit the interaction between molecules, so that the mutual quenching process between the molecules can be relieved to a certain degree. The phenanthroimidazole derivative has bipolar transport properties and excellent thermal stability and chemical stability. The non-doped electroluminescent device prepared by the derivative has the advantages of low turn-on, low roll-off, high efficiency, high color purity and the like, and has a promoting effect on the further development of organic electroluminescence.
Description
Technical Field
The invention belongs to the technical field of organic photoelectric materials, and particularly relates to phenanthroimidazole-based organic blue light micromolecules and application thereof in preparation of non-doped organic electroluminescent devices.
Background
Since the discovery of Organic Light Emitting Diodes (OLEDs) by the kodak company dunqing cloud doctor et al in 1987, the research trend of OLED materials and devices has risen worldwide. Due to the advantages of flexibility, wide viewing angle, energy conservation and the like, the OLED is rapidly developed and has corresponding commercialized products applied to the fields of display and illumination. The blue light material is one of the essential three primary colors in full color display, and in addition, the blue light material can be used as a main body to excite other colors through energy transfer due to a wider forbidden band, so that the manufacturing process of a component for full color display can be simplified, and the stability of a device can be improved.
The standard for deep blue light defined by the american television committee (NTSC) is the blue light coordinate (0.14, 0.08). The saturated deep blue light material is not only beneficial to rich colors of image display, but also can reduce power consumption in full color display. In the field of commercial application, the shortage of high-efficiency, saturated deep blue fluorescent materials has become one of the major bottlenecks that restrict the application of organic electroluminescent devices. Currently, relatively popular phosphorescent and Thermally Activated Delayed Fluorescence (TADF) materials are being investigated to achieve 100% exciton utilization, but they do not solve the problems currently faced by blue light. For phosphorescent materials, when the radiative metal-ligand charge transfer (MLCT) excited state is promoted to a short wavelength emission region, the non-radiative process of the metal d-rail is severe, and the phosphorescent materials are difficult to break through in the deep blue region. For TADF materials, most of them exhibit sky blue and blue-green emission due to the strong charge transfer state characteristic of the excited state, and it is difficult to realize CIEyLess than or equal to 0.08; secondly, since TADF materials involve long-lived intersystem crossing processes and suffer from severe efficiency roll-off at high current densities, they typically need to be fabricated into doped devices, like phosphorescent materials, which increases the complexity and economic cost of device fabrication and reduces the reproducibility of device performance. In addition, the lowest triplet state energy level of the blue TADF material is high, so the requirement on the host material is also strict, and the selection is less. Thus, in CIEyFew undoped devices have a deep blue field of less than or equal to 0.08 and an external quantum efficiency of more than 10%. To solve these problems, it is important to develop a blue organic emitter having high efficiency, high color purity, good chemical and thermal stability, low efficiency roll-off, and simple device manufacturing process.
The phenanthroimidazole compound can be simply synthesized by a one-pot method, the raw material cost is low, modification sites are rich, the inherent bipolar property is favorable for the transmission balance of current carriers, and a rigid plane is favorable for obtaining high fluorescence quantum yield. Besides, the wide forbidden band of the phenanthroimidazole is beneficial to realizing deep blue light emission. The organic micromolecule material with weak charge transfer characteristic is constructed by connecting the organic micromolecule material with neutral groups and weak acceptor groups in a reasonable mode, so that a non-doped device with deep blue light emission can be realized, and high external quantum efficiency under high brightness can be realized.
Disclosure of Invention
The invention aims to solve the problems of low color purity, low device efficiency and serious roll-off of organic blue light micromolecule materials in OLEDs in the field of non-doped devices. The invention provides a phenanthroimidazole-based high-efficiency organic blue-light fluorescent micromolecule material which is simple in synthesis method and excellent in thermal stability. The compounds are applied to the field of electroluminescence, so that excellent characteristics of high-efficiency deep blue light emission, low roll-off under high brightness and the like are realized, and the defects that metal complex phosphorescent materials and TADF materials need to be doped, the efficiency of devices is seriously attenuated under high brightness and the like are overcome.
In order to achieve the above purpose, the organic blue light micromolecule based on phenanthroimidazole has the following structural general formula:
the substituents R1 to R4 may be the same or different and are selected from hydrogen, phenyl, biphenyl, triphenyl, cyano-substituted phenyl, fluorophenyl, difluorophenyl, trifluoromethylphenyl, naphthyl, anthryl, diphenylether, diphenylsulfide, diphenylmethylene, fluorenyl and fluorenyl derivatives, spirofluorenyl and spirofluorenyl derivatives and other aromatic structures.
Preferably, the structural formula of the phenanthroimidazole-based organic blue light micromolecule is shown as one of the following formulas:
the phenanthroimidazole-based organic blue light micromolecule is prepared by preparing a phenanthroimidazole raw material from phenanthrenequinone by a one-pot method and preparing a target compound by utilizing Suzuki coupling.
A non-doped organic electroluminescent device prepared based on the organic blue light micromolecules is composed of a glass substrate, an ITO anode, a hole transport layer, a luminescent layer, an electron transport layer and a cathode, and is characterized in that: the light-emitting layer at least contains one organic blue light micromolecule.
The principle of the invention is as follows: phenanthroimidazole has a large rigid pi plane, has high fluorescence quantum yield, and meanwhile, the wide band gap of phenanthroimidazole contributes to realizing deep blue light emission of derivatives of phenanthroimidazole. The bipolar characteristic of the phenanthroimidazole is beneficial to the transmission balance of current carriers, strong intramolecular charge transfer cannot be caused by connecting neutral groups with the phenanthroimidazole, the construction of molecules with weak charge transfer characteristics is facilitated, and the light color of a target product can be blue-shifted to a short wavelength region. In addition, the group with certain steric hindrance is selected, the distance between molecules is increased, the aggregation quenching phenomenon under the solid state of the molecules is avoided, high solid state luminous efficiency is realized, and a foundation is laid for realizing a high-efficiency non-doped blue light electroluminescent device.
The organic blue light micromolecule luminescent material and the non-doped organic electroluminescent device prepared by the organic blue light micromolecule luminescent material have the following characteristics:
1. the preparation method is simple, the reaction conditions are mild, and the prepared target product has excellent thermal stability and chemical stability.
2. The phenanthroimidazole-based derivative has a proper energy level, is favorable for the transmission and balance of current carriers, and can be used as a blue light material to be applied to the field of organic electroluminescence.
3. The derivative has the characteristic of intramolecular weak charge transfer, can realize saturated blue light emission, and promotes the further development of blue electroluminescent materials.
4. The organic micromolecule is suitable for preparing the non-doped blue light OLED device, the device structure is simpler, and the manufacturing cost is saved.
Drawings
FIG. 1 is a thermogravimetric curve, thermal decomposition temperature (T), of P2d) The temperature is 430 ℃, the thermal stability is good, and a foundation is provided for preparing a luminescent device by vacuum evaporation.
FIG. 2 is a differential scanning calorimetry curve, glass transition temperature (T), of P2g) At 134 ℃ crystallization Peak (T)c) At 225 ℃ melting point (T)m) At 302 ℃; the high crystallization and melting point temperature ensures the morphological stability of the OLED device during working, and can effectively improve the stability of the device efficiency and prolong the service life of the device.
FIG. 3 shows absorption and emission spectra of P2 undoped vapor-deposited film, in which the absorption main peaks are at 334nm and 369nm, and the emission main peak is at 440nm, which is the emission of blue light, and can be used as organic blue light material to prepare electroluminescent device.
FIG. 4 is a graph of luminance-voltage-current density for an undoped electroluminescent device prepared using compound P1 as the light-emitting layer, the maximum luminance of the device being 5634cd m-2The starting voltage is 3.3V;
FIG. 5 is a graph of current efficiency-luminance-energy efficiency, maximum power, of an undoped electroluminescent device prepared using compound P1 as the light-emitting layerFlow efficiency of 2.6cd A-1Maximum power efficiency of 2.0lm W-1；
Fig. 6 is an external quantum efficiency curve of an undoped electroluminescent device prepared by using compound P1 as a light-emitting layer, the maximum external quantum efficiency being 6.1%: inserting a drawing: luminance of 100cd m-2The main peak of the spectrum is 424 nm;
FIG. 7 shows the electroluminescence spectrum of an undoped electroluminescent device prepared by using the compound P1 as a light-emitting layer under different voltages, wherein the main peak of the spectrum is at 424nm, and the high repetition degree of the electroluminescence spectrum under different driving voltages indicates good stability.
FIG. 8 is a graph of luminance-voltage-current density for an undoped electroluminescent device prepared using compound P2 as the light-emitting layer, the maximum luminance of the device being 18637cd m-2The starting voltage is 3.0V;
FIG. 9 is a graph of current efficiency-luminance-energy efficiency for an undoped electroluminescent device prepared using compound P2 as the light-emitting layer, with the maximum current efficiency being 7.2cd A-1Maximum power efficiency of 6.2lm W-1；
Fig. 10 is an external quantum efficiency curve of an undoped electroluminescent device prepared by using compound P2 as a light-emitting layer, the maximum external quantum efficiency being 11.8%: illustration is shown: luminance of 100cd m-2The main peak of the spectrum is at 436 nm;
FIG. 11 shows the electroluminescence spectra of undoped electroluminescent devices prepared by using compound P2 as the light-emitting layer at different voltages, the main peak of the spectrum is at 436nm, and the electroluminescence spectra are stable at different driving voltages.
Detailed Description
The invention is further described below with reference to the drawings and examples to facilitate understanding of the invention by those skilled in the art. It is to be understood that the embodiments described are merely exemplary of the present disclosure, and that all variations, equivalents, and modifications that are obvious to one skilled in the art and may be made in the present disclosure based on the above disclosure are intended to be included within the scope of the present disclosure. The starting materials mentioned below are either commercially available or prepared according to known literature or patents, and the process steps and preparation methods not mentioned are all those well known to the person skilled in the art.
Example 1: the preparation of compound P1 of this example was carried out as follows:
synthesis of M1: m1 was synthesized by a one-pot method by dissolving phenanthrenequinone (2.08g, 10.00mmol), aniline (3.73g, 40.00mmol), 3, 5-dibromobenzaldehyde (2.64g, 10.00mmol) and ammonium acetate (3.85g, 50mmol) in 50mL glacial acetic acid in a 100mL round-bottomed flask and heating at 120 ℃ under reflux for 2 hours. After the reaction, the reaction was quenched with water, filtered to obtain a solid, washed with water, glacial acetic acid and ethanol in this order to obtain a crude product, and subjected to column chromatography to separate and purify the crude product (petroleum ether: dichloromethane volume ratio: 2: 1) to obtain a white solid (4.23g, yield: 80%). Mass Spectrometry MALDI-TOF (M/z) [ M+]: the measured value was 528.77, and the theoretical value was 528.25.
Synthesis of M2: m1(5.28g, 10.00mmol), pinacol diboron (10.12g, 40.00mmol), potassium acetate (5.88g, 60mmol) and [1,1' -bis (diphenylphosphino) ferrocene]Palladium dichloride dichloromethane complex (490mg, 0.6mmol) was dissolved in 80mL of 1, 4-dioxane solution and heated at 85 ℃ under reflux for 48 hours. After completion of the reaction, the reaction mixture was separated by extraction with dichloro, concentrated to give a crude product, and purified by column chromatography (petroleum ether: dichloromethane volume ratio: 2: 3) to give a white solid (3.73g, yield: 60%). Mass spectrometry MALDI-TOF (M/z) [ M+]: the measured value was 622.88, and the theoretical value was 622.38.
Synthesis of P1: 100mL round bottom flask, and2(1.87g, 3.0mmol), bromobenzene (1.13g, 7.2mmol), potassium carbonate (5.53g, 40mmol), tetrakis (triphenylphosphine) palladium (187.20mg, 0.18mmol) were dissolved in 20mL of distilled water and 40mL of toluene and refluxed at 90 ℃ for 24 hours under nitrogen. The separated liquid was extracted with dichloromethane, and concentrated to obtain a crude product, which was purified by column chromatography (petroleum ether: dichloromethane volume ratio: 4: 1) to obtain a white solid (1.25g, yield: 80%). Mass spectrum: MALDI-TOF (M/z) [ M+]: measured value 522.45, theoretical value 522.65; elemental analysis: c39H26N2Theoretical values are C89.63, H5.01, N5.36; the measurements were C89.61, H5.03, N5.36.
Example 2: the preparation of compound P2 of this example was carried out as follows:
synthesis of M3: m3 was synthesized by a one-pot method by dissolving phenanthrenequinone (2.08g, 10.00mmol), aniline (3.73g, 40.00mmol), 4-bromobenzaldehyde (1.85g, 10.00mmol) and ammonium acetate (3.85g, 50mmol) in 50mL glacial acetic acid in a 100mL round-bottomed flask and heating at 120 ℃ under reflux for 2 hours. After the reaction, the reaction was quenched with water, and the reaction was filtered to obtain a solid, which was washed with water, glacial acetic acid, and ethanol in this order to obtain a crude product, which was purified by column chromatography (petroleum ether: dichloromethane volume ratio: 2: 1) to obtain a white solid (3.59g, yield: 80%). Mass Spectrometry MALDI-TOF (M/z) [ M+]: the measured value was 449.55, and the theoretical value was 449.35.
Synthesis of M4: m3(4.49g, 10.00mmol), pinacol diboron (5.06g, 20.00mmol), potassium acetate (2.94g, 30mmol) and [1,1' -bis (diphenylphosphino) ferrocene]Palladium dichloride dichloromethane complex (245mg, 0.3mmol) was dissolved in 80mL of 1, 4-dioxane solution and heated at 85 ℃ under reflux for 48 h. After the reaction is finished, using dichloro to extract, separate liquid, concentrating to obtain crude product, column chromatography separation and purification (petroleum ether: dichloromethane body)Product ratio is 2: 3) obtained as a white solid (3.48g, 70% yield). Mass Spectrometry MALDI-TOF (M/z) [ M+]: the measured value was 496.39, and the theoretical value was 496.42.
Synthesis of P2: a100 mL round-bottom flask was prepared by dissolving M4(1.49g, 3.0mmol), 5' -bromo-M-terphenyl (1.11g, 3.6mmol), potassium carbonate (5.53g, 40mmol), tetrakis (triphenylphosphine) palladium (93.60mg, 0.09mmol) in 20mL distilled water and 40mL toluene and refluxing at 90 ℃ for 24 hours under nitrogen. The resulting extract was extracted with dichloromethane, concentrated to obtain a crude product, and purified by column chromatography (petroleum ether: dichloromethane volume ratio: 4: 1) to obtain a white solid (1.25g, yield: 80%). Mass spectrum: MALDI-TOF (M/z) [ M+]: measured value 598.24, theoretical value 598.75; elemental analysis: c45H30N2Theoretical values of C90.27, H5.05 and N4.68; the measurements were C90.29, H5.04, N4.67.
Example 3: the preparation of compound P3 of this example was carried out as follows:
this embodiment is substantially the same as embodiment 2, except that: in this example, 5' -bromo-m-terphenyl was exchanged for an equivalent amount of 4-bromo-5 ' -phenyl-1, 1':3', 1' -terphenyl to obtain a white powdery solid (1.35g, yield: 80%). Mass spectrum: MALDI-TOF (M/z) [ M+]: measured value 674.27, theoretical value 674.85; elemental analysis: c51H34N2Theoretical values of C90.77, H5.08, N4.15; the measurements were C90.73, H5.09, N4.17.
Example 4: the preparation of compound P4 of this example was carried out as follows:
this embodiment is substantially the same as embodiment 2, except that: in this example, 5' -bromo-m-terphenyl was exchanged for an equivalent amount of 3-bromo-5 ' -phenyl-1, 1':3', 1' -terphenyl to obtain a white powdery solid (1.35g, yield: 80%). Mass spectrum: MALDI-TOF (M/z) [ M+]: measured value 674.27, theoretical value 675.05; elemental analysis: c51H34N2Theoretical values of C90.77, H5.08, N4.15; the measurements were C90.73, H5.09, N4.17.
Example 5: the preparation of compound P5 of this example was carried out as follows:
this embodiment is substantially the same as embodiment 1, except that: in this example, 5' -bromo-m-terphenyl was used in the amount equivalent to that of bromobenzene to obtain white powdery solid (1.73g, yield: 70%). Mass spectrum: MALDI-TOF (M/z) [ M+]: measured value 826.33, theoretical value 827.04; elemental analysis: c63H42N2Theoretical values of C91.49, H5.12 and N3.39; the measurements were C91.46, H5.14, N3.40.
Example 6: the preparation of compound P6 of this example was carried out as follows:
this embodiment is substantially the same as embodiment 2, except that: in this example, 5' -bromo-m-terphenyl was changed to 4-bromobiphenyl in an equivalent amount to obtain a white powdery solid (1.25g, yield: 80%). Mass spectrum: MALDI-TOF (M/z) [ M+]: measured value 522.21, theoretical value 522.65; elemental analysis: c39H26N2Theoretical values of C89.63, H5.01 and N5.36; the measurements were C89.64, H5.02, N5.34.
Example 7: the preparation of compound P7 of this example was carried out as follows:
this embodiment is substantially the same as embodiment 2, except that: in this example, 5' -bromo-m-terphenyl was converted to m-bromobiphenyl in an equivalent amount to obtain a white powdery solid (1.25g, yield: 80%). Mass spectrum: MALDI-TOF (M/z) [ M+]: measured value 522.21, theoretical value 522.65; elemental analysis: c39H26N2Theoretical values are C89.63, H5.01, N5.36; the measurements were C89.64, H5.02, N5.34.
Example 8: the preparation of compound P8 of this example was carried out as follows:
this embodiment is substantially the same as embodiment 2, except that: in this example, 5' -bromo-m-terphenyl was exchanged for an equivalent amount of 4-bromobiphenyl ether to obtain a white powdery solid (1.29g, yield: 80%). Mass spectrum: MALDI-TOF (M/z) [ M+]: measured value 538.20, theoretical value 538.65; elemental analysis: c39H26N2Theoretical values of O are C89.96, H4.87 and N5.20; the measurements were C89.94, H4.89, N5.20.
Example 9: the preparation of compound P9 of this example was carried out as follows:
this embodiment is substantially the same as embodiment 2, except that: in this example, 5' -bromo-m-terphenyl was converted to 4-bromodiphenylmethane in an equivalent amount to obtain a white powdery solid (1.29g, yield: 80%). Mass spectrum: MALDI-TOF (M/z) [ M+]: measured value 536.23, theoretical value 536.68; elemental analysis: c40H28N2Theoretical valueIs C89.52, H5.26, N5.22; the measurements were C89.54, H5.28, N5.20.
Example 10: the preparation of compound P10 of this example was carried out as follows:
this embodiment is substantially the same as embodiment 2, except that: in this example, 5' -bromo-m-terphenyl was exchanged for an equivalent amount of 2-bromo-9, 9-dimethylfluorene to obtain a white powdery solid (1.35g, yield: 80%). Mass spectrum: MALDI-TOF (M/z) [ M+]: measured value 562.25, theoretical value 563.75; elemental analysis: c42H30N2Theoretical values of C89.65, H5.37 and N4.98; the measurements were C89.67, H5.39, N4.94.
Example 11: the preparation of compound P11 of this example was carried out as follows:
this embodiment is substantially the same as embodiment 2, except that: in this example, 5' -bromo-m-terphenyl was exchanged for an equivalent amount of 2-bromo-9, 9-diphenylfluorene to obtain a white powdery solid (1.65g, yield: 80%). Mass spectrum: MALDI-TOF (M/z) [ M+]: measured value 686.72, theoretical value 686.68; elemental analysis: c52H34N2Theoretical values of C90.93, H4.99 and N4.08; the measurements were C90.91, H4.99, N4.10.
Example 12: the preparation of compound P12 of this example was carried out as follows:
this embodiment is substantially the same as embodiment 2, except that: in this case, 5' -bromo-m-terphenyl is converted into 2-bromo-9, 9-spirobifluorene in equal amount to obtainTo a white powdery solid (1.64g, yield: 80%). Mass spectrum: MALDI-TOF (M/z) [ M+]: measured value 684.26, theoretical value 684.84; elemental analysis: c52H32N2Theoretical values of C91.20, H4.71 and N4.09; the measured values were C91.19, H4.73, N4.08.
Example 13: the preparation of compound P13 of this example was carried out as follows:
this embodiment is substantially the same as embodiment 2, except that: in this example, 5' -bromo-m-terphenyl was exchanged for p-bromophenonitrile in an equivalent amount to give a pale green powdery solid (1.13g, yield: 80%). Mass spectrum: MALDI-TOF (M/z) [ M+]: measured value 471.17, theoretical value 471.56; elemental analysis: c34H21N3Theoretical values of C86.60, H4.49 and N8.91; the measurements were C86.58, H4.50, N8.92.
Example 14: the preparation of compound P14 of this example was carried out as follows:
this embodiment is substantially the same as embodiment 2, except that: in this example, 5' -bromo-m-terphenyl was converted to an equivalent amount of 1-bromo-3, 5-difluorobenzene to obtain a white powdery solid (1.16g, yield: 80%). Mass spectrum: MALDI-TOF (M/z) [ M+]: measured value 482.16, theoretical value 482.53; elemental analysis: c33H20F2N2Theoretical values of C82.14, H4.18, N5.81; the measurements were C82.12, H4.16, N5.82.
Example 15: the preparation of compound P15 of this example was carried out as follows:
this embodiment is substantially the same as embodiment 2, except that: in this example, 5' -bromo-m-terphenyl was exchanged for p-bromotrifluorotoluene in an equivalent amount to obtain a white powdery solid (1.16g, yield: 80%). Mass spectrum: MALDI-TOF (M/z) [ M+]: measured value 514.17, theoretical value 514.55; elemental analysis: c34H21F3N2Theoretical values of C79.37, H4.11, N5.44; the measurements were C79.35, H4.12, N5.45.
Effect examples 1 to 15
The following embodiments of the undoped electroluminescent device prepared by using the materials P1-P15 of the invention have the following specific device preparation process and device performance test experimental operations: preparation of Indium Tin Oxide (ITO) conductive glass substrate: the substrate is sequentially washed by deionized water, isopropanol, acetone, toluene, acetone and isopropanol in an ultrasonic bath for 20 minutes respectively, and is dried in an oven for standby. Treating the surface of the ITO conductive glass in an ultraviolet ozone cleaning machine for 40 minutes, and then transferring the ITO conductive glass into vacuum evaporation equipment (the pressure in a cavity is less than 2 multiplied by 10)-4Pa); vacuum evaporating a hole injection layer HATCN on the anode ITO conductive glass, wherein the thickness of the hole injection layer HATCN is 6 nm; on the HATCN, a hole transport layer TAPC was vacuum evaporated to a thickness of 25 nm: performing vacuum evaporation on the TAPC to form an exciton blocking layer TCTA with the thickness of 15 nm; vacuum evaporating a luminescent layer on TCTA, wherein the thickness of the luminescent layer is 20 nm; vacuum evaporating an electron transport layer TmPyPB on the P1, wherein the thickness is 40 nm; vacuum evaporating an electron injection layer LiF on the TmPyPB, wherein the thickness of the electron injection layer LiF is 1 nm; on LiF, cathode Al is evaporated in vacuum with a thickness of 120 nm.
The organic electroluminescent non-doped device has the following structure: ITO/HATCN (6nm)/TAPC (25nm)/TCTA (15nm)/EML (20nm)/TmPyPB (40nm)/LiF (1nm)/Al (120nm), wherein EML represents a light-emitting layer, and the light-emitting layer is a non-doped thin film formed by vacuum evaporation of the material.
Direct current voltage was applied to the organic electroluminescent device prepared in this example, the luminescence property was evaluated using a Spectrascan PR655 luminance meter, and the current-voltage characteristics were measured using a computer-controlled Keithley 2400 digital source meter. As the light emission characteristics, parameters such as the on voltage, the maximum luminance, the emission peak position, the CIE color coordinate value, the external quantum efficiency, etc. were measured as a function of the applied dc voltage, and the results of the effect examples are shown in tables 1 to 3.
Table 1: effects electroluminescent property data of device of example 1
Table 2: effect example 2 electroluminescent property data of device
Table 3: effect examples 1 to 15 electroluminescent property data of devices
Effect examples 1 to 15 the structural formulae of the materials used in the organic electroluminescent devices are as follows, and they are commercially available:
the above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents, improvements and the like that fall within the spirit and principle of the present invention are intended to be included therein.
Claims (4)
1. A phenanthroimidazole-based organic blue light micromolecule material has a structural general formula as follows:
wherein, the substituents R1-R4 are the same or different and are selected from hydrogen, phenyl, biphenyl, triphenyl, cyano-substituted phenyl, fluorophenyl, difluorophenyl, trifluoromethylphenyl, naphthyl, anthryl, diphenyl ether, diphenyl sulfide, diphenyl methane, fluorenyl and fluorenyl derivatives or spirofluorenyl and spirofluorenyl derivatives.
2. The phenanthroimidazole-based organic blue-light small molecule material of claim 1, having a structural formula shown in one of the following:
3. the use of the phenanthroimidazole-based organic blue light small molecule material in claim 1 or 2 in the preparation of non-doped organic electroluminescent devices.
4. The application of the phenanthroimidazole-based organic blue-light small molecule material in preparing a non-doped organic electroluminescent device as claimed in claim 3, wherein: the structure of the undoped organic electroluminescent device is anode/hole injection layer/hole transport layer/organic luminescent layer/electron transport layer/electron injection layer/cathode, and the organic luminescent layer at least contains one phenanthroimidazole-based organic blue light micromolecule material in claim 1 or 2.
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