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CN113336782A - Green light narrow spectrum three-coordination boron luminescent compound containing carbazole skeleton, preparation method and application thereof - Google Patents

Green light narrow spectrum three-coordination boron luminescent compound containing carbazole skeleton, preparation method and application thereof Download PDF

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CN113336782A
CN113336782A CN202110691228.XA CN202110691228A CN113336782A CN 113336782 A CN113336782 A CN 113336782A CN 202110691228 A CN202110691228 A CN 202110691228A CN 113336782 A CN113336782 A CN 113336782A
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路萍
刘福通
靳海旭
程状
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Changchun Hyperions Technology Co Ltd
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Abstract

一类含咔唑骨架的绿光窄光谱三配位硼发光化合物、制备方法及其在有机电致发光器件中的应用，属于有机半导体发光器件技术领域。本发明的有机电致发光材料是以含咔唑骨架的绿光窄光谱三配位硼发光化合物为中心、在整个分子骨架外围引入大的空间位阻基团，可以撑开了分子间距，有效的抑制分子之间的相互作用，缓解效率滚降问题，有利于在亮度下获得高的效率；此外刚柔适度的共轭结构可以降低分子的重组能，使分子激发态下的结构形变小，得到具有窄光谱(半峰宽<30nm)的高效有机电致发光化合物。通过真空蒸镀的方法制备有机电致发光器件的发光层，由此制备了具有高效率、高色纯度的有机电致发光器件，在全彩显示技术得到应用。

Figure 202110691228

The invention discloses a green light narrow-spectrum tri-coordinate boron luminescent compound containing a carbazole skeleton, a preparation method and its application in an organic electroluminescent device, and belongs to the technical field of organic semiconductor light-emitting devices. The organic electroluminescent material of the present invention is centered on a green light narrow-spectrum tri-coordinated boron luminescent compound containing a carbazole skeleton, and large steric hindrance groups are introduced at the periphery of the entire molecular skeleton, which can open the molecular distance and effectively In addition, the moderately rigid and flexible conjugated structure can reduce the reorganization energy of the molecule, so that the structural deformation in the excited state of the molecule is small, Highly efficient organic electroluminescent compounds with narrow spectra (half width <30 nm) were obtained. The light-emitting layer of the organic electroluminescent device is prepared by the method of vacuum evaporation, thereby preparing the organic electroluminescent device with high efficiency and high color purity, which is applied in the full-color display technology.

Figure 202110691228

Description

Green light narrow spectrum three-coordination boron luminescent compound containing carbazole skeleton, preparation method and application thereof
Technical Field
The invention belongs to the technical field of organic semiconductor luminescent devices, and particularly relates to a novel efficient green light narrow-spectrum three-coordination boron luminescent compound containing a carbazole skeleton, a preparation method and application thereof in an organic electroluminescent device.
Background
An Organic Light Emitting Diode (OLED) is a novel light emitting device, has the advantages of flexibility, wide viewing angle, energy saving, high response speed and the like, has made a great progress in full-color display and illumination application technologies, and has become a hot trend of current industrialization. The organic electroluminescent device is a laminated structure consisting of a plurality of organic functional layers and electrodes. The organic functional layer comprises an injection layer, a transmission layer, a barrier layer, a light-emitting layer and the like. The luminescent layer is used as the core of the electroluminescent device to determine the efficiency and the light color of the device, and the development and research of the material of the luminescent layer are more widely concerned. Organic small molecule photoelectric materials are widely used as high-performance materials due to the advantages of definite structure, easy modification, simple purification and processing and the like.
Thermally-Activated Delayed Fluorescence (TADF) materials are widely developed and used in electronic devices because of the 100% internal quantum efficiency that can be achieved (Nature 2012,492, 234;. j.am. chem. soc.2012,134, 14706-14709; nat. photonics 2014,8, 326;) materials. The Reverse Intersystem Crossing (RISC) process from a triplet state to a singlet state is realized by utilizing a charge transfer state bound by weak excitons, 25 percent of singlet excitons and 75 percent of triplet excitons can be simultaneously utilized to obtain high luminous efficiency which is comparable to a phosphorescent device, and the development trend of the OLED field is led. At present, although the TADF material is introduced into the OLED device as the luminescent dye, the efficiency can be high, but the color purity is very poor in most cases, and the technical requirement of high color purity of the full-color display technology cannot be met, and a novel material system with high efficiency and high color purity is urgently needed to be developed.
The TADF emission is mainly due to intramolecular charge transfer transition, which causes relaxation of molecular structure and resonance and transition motion to the acceptor, so that the TADF luminescent material shows a broad emission peak without fine structure, and its full-width at half-maximum (FWHM) is approximately distributed between 80-100 nm. The wide spectrum is favorable for illumination application, but cannot meet the requirements of high resolution, high definition and high color gamut in the display field. Although the device structure adopting the optical filter or the optical microcavity can meet the requirement of displaying on color purity, the device structure is complex, and simultaneously, the device structure causes great energy loss, which is not favorable for the requirements of energy conservation and environmental protection. Therefore, the development of a novel highly efficient and narrow-spectrum TADF luminescent material can fundamentally solve the problem of impure light emission of a device, and is a new research hotspot in the field of OLED.
In recent years, multiple resonance effect (MR) TADF materials have been widely used in scientific research and industrial fields (adv. Mater.2016,28, 2777-. Although rigid structures can effectively suppress non-radiative transitions, large planar structures tend to interact between molecules in the solid state, reducing the luminous efficiency of the material, and even causing severe efficiency roll-off in electroluminescent devices. In addition, although some electron-withdrawing groups or heavy atoms can adjust the color of the luminescent light, the structural relaxation, vibration and transport of the molecule are inevitably increased, so that the reorganization energy (lambda) is increased, and the spectrum is widened (FWHM >30 nm).
Disclosure of Invention
The invention aims to solve the technical problems that the efficiency roll-off is serious in the existing narrow-spectrum TADF material system, the spectrum is still wider (FWHM is more than 30nm), and the spectrum cannot be narrowed greatly. The organic electroluminescent device which is lack of device structure, simple manufacturing process, low cost, high efficiency, stability and high color purity is beneficial to commercial application.
According to the invention, a green light narrow spectrum three-coordination boron luminescent compound containing a carbazole skeleton is taken as a center, and a large steric hindrance group is introduced to the periphery of the whole molecular skeleton, so that the molecular distance can be expanded, the interaction between molecules can be effectively inhibited, the problem of efficiency roll-off can be alleviated, and high efficiency can be obtained under the brightness; in addition, the conjugated structure with moderate rigidity and flexibility can reduce the recombination energy of molecules, so that the structural configuration of the molecules in an excited state becomes small, and the high-efficiency organic electroluminescent compound with a narrow spectrum (FWHM is less than 30nm) is obtained. The light-emitting layer of the organic electroluminescent device is prepared by a vacuum evaporation method, and the prepared organic electroluminescent device realizes TADF emission with narrow spectrum.
In order to achieve the purpose, the green light narrow spectrum three-coordination boron luminescent compound containing the carbazole skeleton has the following structural formula:
Figure BDA0003126832910000021
wherein R is a bulky sterically hindered group.
Further, the green light narrow spectrum three-coordination boron luminescent compound containing the carbazole skeleton has a structural formula shown as one of the following formulas:
Figure BDA0003126832910000031
Figure BDA0003126832910000041
the organic electroluminescent device prepared by the product of the invention consists of a cathode, an anode and a plurality of organic functional layers between the two electrodes, wherein at least one layer of the organic functional layers is a luminous layer. The electroluminescent device can be used for preparing an organic electroluminescent display or an organic electroluminescent lighting source.
Further, the electroluminescent device prepared by the product of the invention sequentially comprises a transparent substrate, an ITO conductive film (anode), a hole injection layer (HATCN), a hole transport layer (TAPC), an exciton blocking layer (TCTA and mCP), a light emitting layer, an electron transport layer (TmPyPB), an electron injection Layer (LiF) and a cathode layer (Al) from bottom to top. All functional layers can adopt a vacuum evaporation film-forming process.
Preferably, some of the organic compounds used in the device are commercially available or prepared according to known literature or patents, and the molecular structural formula is shown below:
Figure BDA0003126832910000051
preferably, the light-emitting layer contains (in the light-emitting layer, the compound of the invention is used as a doping material, and is doped into a host material for use, the host material is mCBP, and the doping mass concentration is 2-5%) any one of the green light narrow-spectrum three-coordination boron light-emitting compounds containing a carbazole skeleton.
The unique properties of the materials of the present invention are illustrated below by taking the compound BN-1 as an example, and the other organic molecules of the present invention have the same molecular skeleton as the compound BN-1, and thus have the same basic characteristics as the compound BN-1. Compared with some of the disclosed three-coordinate boron derivatives (CN 110627822A, CN 111333671A, Angew. chem. Int.Ed.2019,58, 169912-169917, Angew. chem. Int.Ed.2020, 59,17442-17446), the organic small molecule luminescent material and the electroluminescent device thereof have the following characteristics:
1. the large steric hindrance groups (terphenyl, fluorene and spirofluorene) are introduced to the molecular skeleton of the three-coordinate boron derivative for the first time, so that the molecular spacing can be effectively expanded, the pi-pi interaction caused by a large conjugated plane in a solid state is inhibited, and the solid state light-emitting efficiency is high.
2. The quantum chemical theory calculation shows that the introduction of the peripheral group substituted by the single bond can effectively inhibit the high-frequency carbon-carbon stretching vibration of the molecule, the low-frequency vibration mainly comprising torsional vibration is dominant, the recombination energy of the molecule is reduced, the structural configuration of the molecule in an excited state is reduced, and the half-peak width (FWHM is less than 30nm) of the target molecule is further narrowed.
3. Because the interaction between molecules is inhibited, the quenching or annihilation of triplet excitons can be relieved in the electroluminescent device, the efficiency roll-off is reduced to a certain extent, and the realization of high efficiency under high brightness is facilitated.
4. The device of the compound has simple preparation process, only selects single main body material, avoids the cost increase caused by using exciplex or sensitized main body, and is suitable for mass production and amplification.
Drawings
FIG. 1: the structure of the organic electroluminescent device prepared by the invention is shown in the figure, wherein 1 is a transparent glass substrate, 2 is an ITO conductive film anode, 3-bit hole injection layer, 4 is a hole transport layer, 5 is an exciton blocking layer, 6 is an organic luminescent layer, 7 is an electron transport layer, and 8 is a cathode;
FIG. 2: an optimized configuration diagram of recombination energy, ground state and excited state of the compound BN-1; the recombination energy of the molecule is calculated to be very small, 0.1088eV, by utilizing the time-dependent density functional theory (TDDFT), and the structural relaxation of the molecule is greatly inhibited by the rigid conjugated molecular skeleton of the molecule;
FIG. 3: ultraviolet (Uv-Vis), fluorescence (PL) and low temperature phosphorescence (Phos) spectra of compound BN-1; it can be seen from the graph that the FWHM of BN-1 is 21nm, and the difference of single/triplet state energy levels (. DELTA.E)ST) 0.09 eV;
FIG. 4: delayed fluorescence decay curve (doping concentration 3 wt%) of a doped thin film of the compound BN-1; illustration is shown: a transient fluorescent component of a doped thin film of compound BN-1; the lifetimes of the instant fluorescence and the delayed fluorescence are respectively 4.9ns and 62 mus through fitting;
FIG. 5: external quantum efficiency curves for electroluminescent devices made with compound BN-1, inset: electroluminescence spectrum under 6V driving voltage; the electroluminescence spectrum is 492nm, the half-peak width is 28nm, and the maximum external quantum efficiency is 28.9%.
FIG. 6: the electroluminescent spectrum of the electroluminescent device prepared by the compound BN-1 under different voltages; the spectra at different voltages are very stable, demonstrating the color stability of the device.
FIG. 7: the current density-voltage-luminance curve of an electroluminescent device prepared from the compound BN-1; the turn-on voltage of the device was 3.7V and the maximum luminance was 13518cd/m2；
FIG. 8: current efficiency-luminance-power efficiency curves for electroluminescent devices prepared with compound BN-1. The maximum current efficiency and power efficiency of the device are respectively 54.8cd/A and 43.1 lm/W.
Detailed Description
The present invention is further described below in conjunction with the appended drawings to facilitate an understanding of the present invention by those skilled in the art. It is obvious that the embodiments described are only a part of the experiments and not all embodiments, and those skilled in the art should be able to make non-essential modifications, equivalent replacements and improvements of the present invention according to the above-mentioned disclosure within the protection scope of the present invention. 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 those well known to the person skilled in the art.
Example 1: preparation of BN-1 according to this example, the procedure was as follows:
Figure BDA0003126832910000071
synthesis of M1: 100mL of a solution of 11.2g of 3, 6-di-tert-butylcarbazole (40.0mmol) in anhydrous DMF (N, N-dimethylformamide) was slowly added dropwise to 50mL of a solution of 26.1g of cesium carbonate (80.0mmol) in anhydrous DMF, and after stirring at room temperature for 2 hours, 20mL of a solution of 5-bromo-2-chloro-1, 3-difluorobenzene (20.0mmol) in anhydrous DMF was added dropwise thereto. The reaction was stirred at 150 ℃ for 24 hours. Then cooling to room temperature, pouring into 1L of ice water, filtering to obtain a white solid, drying in vacuum, and separating and purifying by column chromatography, wherein a developing agent is petroleum ether: dichloromethane (volume ratio 5: 1) gave a white solid (12.1 g, yield: 81%). Mass Spectrometry MALDI-TOF (M/z) [ M+]: the measured value was 745.96, and the theoretical value was 746.27.
Figure BDA0003126832910000081
Synthesis of M2: in a 250mL round bottom flask, (3, 5-diphenylphenyl) boronic acid (4.11g, 15.0mmol), M1(11.19g, 15.0mmol), palladium tetrakistriphenylphosphine (480mg, 0.42mmol), potassium carbonate (13.8g, 100 mmol) were dissolved in 100mL toluene and 50mL aqueous solution and refluxed at 85 ℃ 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: 10: 1) to obtain a white solid (8.73g, yield: 65%). Mass Spectrometry MALDI-TOF (M/z) [ M+]: the measured value was 895.53, and the theoretical value was 895.67.
Figure BDA0003126832910000082
Synthesis of BN-1: 13.8mL of a solution of tert-butyllithium in n-hexane (18.0mmol) were slowly added to a solution of 8.10g of M2(9.0mmol) in 100mL of tert-butylbenzene (0 ℃ C.) under a nitrogen atmosphere. The temperature was slowly raised to 60 ℃ and after stirring for 2 hours, n-hexane was removed in vacuo, then cooled to-40 ℃ and 1.7 mL of boron tribromide (18.0mmol) was added and the reaction mixture was stirred at room temperature for 0.5 hours. Then 3.1mL of N, N-diisopropylethylamine (18.0mmol) was added at 0 deg.C, and the reaction mixture was warmed to 120 deg.C and stirred for an additional 5 hours before cooling to room temperature. To the reaction mixture was added 5mL of methanol to quench the residual boron tribromide. The reaction system was concentrated in vacuo and purified by column chromatography (petroleum ether: dichloromethane volume ratio: 10: 1) to give a yellow solid (1.95g, yield: 25%). Mass Spectrometry MALDI-TOF (M/z) [ M+]: the measured value was 869.31, and the theoretical value was 869.02. Elemental analysis results: experimental values (%): c, 88.54; h, 7.01; b, 1.23; n, 3.23; theoretical value (%): c, 88.46; h, 7.08; b, 1.24; and N, 3.22.
Figure BDA0003126832910000083
Example 2: the procedure for the preparation of BN-2 of this example was as follows:
Figure BDA0003126832910000091
this embodiment is substantially the same as embodiment 1, except that: in this example, (3, 5-diphenylbenzene) boronic acid was changed to an equivalent amount of 2,4, 6-trimethylphenylboronic acid to obtain a pale yellow powdery solid (2.19g, yield: 32%). Mass Spectrometry MALDI-TOF (M/z) [ M+]: the measured value was 758.19, and the theoretical value was 758.90. Elemental analysis results: experimental values (%): c, 87.13; h, 7.75; b, 1.42; n, 3.71; theoretical value (%): c, 87.05; h, 7.84; b, 1.42; and N, 3.69.
Example 3: the procedure for the preparation of BN-3 according to this example was as follows:
Figure BDA0003126832910000092
this embodiment is substantially the same as embodiment 1, except that: in this example, (3, 5-diphenylbenzene) boronic acid was changed to 4- (9H-carbazol-9-yl) phenylboronic acid in an equivalent amount to obtain a yellow powdery solid (1.75g, yield: 22%). Mass Spectrometry MALDI-TOF (M/z) [ M+]: the measured value was 882.45, and the theoretical value was 882.02. Elemental analysis results: experimental values (%): c, 87.25; h, 6.79; b, 1.22; n, 4.73; theoretical value (%): c, 87.15; h, 6.86; b, 1.23; and N, 4.76.
Example 4: the procedure for the preparation of BN-4 of this example was as follows:
Figure BDA0003126832910000101
this embodiment is substantially the same as embodiment 1, except that: in this example, (3, 5-diphenylbenzene) boronic acid was changed to an equivalent amount of 3- (9H-carbazol-9-yl) phenylboronic acid to obtain a yellow powdery solid (1.59g, yield: 20)%). Mass Spectrometry MALDI-TOF (M/z) [ M+]: the measured value was 882.31, and the theoretical value was 882.02. Elemental analysis results: experimental values (%): c, 87.23; h, 6.77; b, 1.22; n, 4.75; theoretical value (%): c, 87.15; h, 6.86; b, 1.23; and N, 4.76.
Example 5: the procedure for the preparation of BN-5 of this example was as follows:
Figure BDA0003126832910000102
this embodiment is substantially the same as embodiment 1, except that: in this case, (3, 5-diphenylbenzene) boronic acid is exchanged for an equivalent amount of (3',4',5' -triphenyl- [1,1:2, 1- "terphenyl)]4-yl) boronic acid to give a yellow powdery solid (1.12g, yield: 11%). Mass Spectrometry MALDI-TOF (M/z) [ M+]: the measured value was 1097.65, and the theoretical value was 1097.31. Elemental analysis results: experimental values (%): c, 87.89; h, 6.77; b, 1.01; n, 2.54; theoretical value (%): c, 87.96; h, 6.71; b, 0.99; and N, 2.55.
Example 6: the procedure for the preparation of BN-6 of this example was as follows:
Figure BDA0003126832910000111
this embodiment is substantially the same as embodiment 1, except that: in this example, (3, 5-diphenylbenzene) boronic acid was changed to an equivalent amount of (5,6,7, 8-tetraphenylnaphthalen-2-yl) boronic acid to obtain a yellow powdery solid (1.01 g, yield: 10%). Mass Spectrometry MALDI-TOF (M/z) [ M+]: the measured value was 1071.53, and the theoretical value was 1071.27. Elemental analysis results: experimental values (%): c, 89.65; h, 6.71; b, 1.03; n, 2.59; theoretical value (%): c, 89.70; h, 6.68; b, 1.01; and N, 2.62.
Example 7: the procedure for the preparation of BN-7 of this example was as follows:
Figure BDA0003126832910000112
this embodiment is substantially the same as embodiment 1, except that: in this example, (3, 5-diphenylbenzene) boronic acid was changed to the equivalent amount of 9, 9-dimethylfluorene-3-boronic acid pinaster to give a yellow powdery solid (1.45 g, yield: 19%). Mass Spectrometry MALDI-TOF (M/z) [ M+]: the measured value was 832.69, and the theoretical value was 832.98. Elemental analysis results: experimental values (%): c, 87.91; h, 7.41; b, 1.33; n, 3.32; theoretical value (%): c, 87.96; h, 7.38; b, 1.30; and N, 3.36.
Example 8: the procedure for the preparation of BN-8 of this example was as follows:
Figure BDA0003126832910000121
this embodiment is substantially the same as embodiment 1, except that: in this example, (3, 5-diphenylbenzene) boronic acid was changed to the equivalent amount of 9, 9-dimethylfluorene-2-boronic acid pinacol ester to obtain a yellow powdery solid (1.35g, yield: 18%). Mass Spectrometry MALDI-TOF (M/z) [ M+]: the measured value was 832.76, and the theoretical value was 832.98. Elemental analysis results: experimental values (%): c, 87.90; h, 7.43; b, 1.32; n, 3.33; theoretical value (%): c, 87.96; h, 7.38; b, 1.30; and N, 3.36.
Example 9: the procedure for the preparation of BN-9 of this example was as follows:
Figure BDA0003126832910000122
this embodiment is substantially the same as embodiment 1, except that: in this example, (3, 5-diphenylbenzene) boronic acid was changed to the equivalent amount of 9, 9-dimethylfluorene-4-boronic acid pinacol ester to give a yellow powdery solid (1.21g, yield: 16%). Mass Spectrometry MALDI-TOF (M/z) [ M+]: the measured value was 832.45, and the theoretical value was 832.98. Elemental analysis results: experimental values (%): c, 87.92; h, 7.43; b, 1.32; n, 3.35; theoretical value (%): c, 87.96; h, 7.38; b, 1.30; and N, 3.36.
Example 10: the procedure for the preparation of BN-10 of this example is as follows:
Figure BDA0003126832910000131
this embodiment is substantially the same as embodiment 1, except that: in this example, (3, 5-diphenylbenzene) boronic acid was changed to an equivalent amount of 9,9' -spirobifluorene-3-boronic acid to obtain a yellow powdery solid (1.35g, yield: 16%). Mass Spectrometry MALDI-TOF (M/z) [ M+]: the measured value was 955.45, and the theoretical value was 955.11. Elemental analysis results: experimental values (%): c, 89.16; h, 6.72; b, 1.12; n, 2.95; theoretical value (%): c, 89.29; h, 6.65; b, 1.13; and N, 2.93.
Example 11: the procedure for the preparation of BN-11 of this example was as follows:
Figure BDA0003126832910000132
this embodiment is substantially the same as embodiment 1, except that: in this example, (3, 5-diphenylbenzene) boronic acid was changed to an equivalent amount of 9,9' -spirobifluorene-2-boronic acid to obtain a yellow powdery solid (1.23g, yield: 14%). Mass Spectrometry MALDI-TOF (M/z) [ M+]: the measured value was 955.63, and the theoretical value was 955.11. Elemental analysis results: experimental values (%): c, 89.26; h, 6.70; b, 1.11; n, 2.94; theoretical value (%): c, 89.29; h, 6.65; b, 1.13; and N, 2.93.
Example 12: the procedure for the preparation of BN-12 of this example was as follows:
Figure BDA0003126832910000141
this embodiment is substantially the same as embodiment 1, except that: in this example, (3, 5-diphenylbenzene) boronic acid was changed to an equivalent amount of 9,9' -spirobifluorene-4-boronic acid to obtain a yellow powdery solid (1.03g, yield: 12%). Mass spectrometryMALDI-TOF(m/z)[M+]: the measured value was 955.32, and the theoretical value was 955.11. Elemental analysis results: experimental values (%): c, 89.25; h, 6.71; b, 1.15; n, 2.91; theoretical value (%): c, 89.29; h, 6.65; b, 1.13; and N, 2.93.
Effect example 1: preparation of organic electroluminescent device BN-1
The technical effects and advantages of the invention are shown and verified by testing practical use performance by specifically applying the compound of the invention to an organic electroluminescent device. The specific device preparation process and device performance test experiment operation are as follows: the preparation process of the device is as follows: preparation of substrate Indium Tin Oxide (ITO) conductive glass: the substrate is sequentially washed by deionized water, isopropanol, acetone, toluene, acetone and isopropanol in an ultrasonic bath for 20 minutes respectively, and 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 ITO conductive film, 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 30 nm: evaporating an exciton blocking layer TCTA on TAPC, wherein the thickness is 5 nm; evaporating an exciton blocking layer mCP on the TCTA, wherein the thickness of the exciton blocking layer mCP is 5 nm; depositing a luminescent layer on the mCP with a thickness of 20 nm; an electron transport layer TmPyPB is evaporated on the luminescent layer, and the thickness is 40 nm; evaporating an electron transport layer LiF on TPBi, wherein the thickness of the electron transport layer LiF is 1 nm; on LiF, a cathode Al is evaporated to a thickness of 100 nm.
The organic electroluminescent device BN-1 has the following structure: ITO/HATCN (6nm)/TAPC (30 nm)/TCTA (5nm)/mCP (5nm)/EML (20nm)/TmPyPB (40nm)/LiF (1nm)/Al (100nm), wherein EML represents a light-emitting layer, and the light-emitting layer is composed of a host material mCBP with the mass percentage of 97% and a doped guest light-emitting material BN-1 with the mass percentage of 3%.
A direct current voltage was applied to the organic electroluminescent device BN-1 prepared in this example, the luminescence performance 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 luminescence characteristics, the electroluminescence spectrum and half-peak under the variation with the applied DC voltage were measuredWide, CIE color coordinate value, external quantum efficiency (%), Power efficiency (lm/W), maximum luminance (cd/m)2). The luminance-voltage-current density curve, the current efficiency-luminance-energy efficiency curve, the external quantum efficiency curve, and the electroluminescence spectra at different voltages of the organic electroluminescent device of the present example are shown in fig. 4, 5,6, and 7, respectively. Detailed electroluminescent performance data for the devices are listed in table 1. The measured values of the fabricated device were 492nm in spectral peak, 28nm in half-peak width, CIE color coordinate values (0.10, 0.46), 28.9% in maximum external quantum efficiency, 43.1lm/W in maximum power efficiency, and 13518cd/m in maximum luminance2。
Effect example 2: preparation of organic electroluminescent device BN-2
The same preparation method as that of effect example 1 except that the guest light emitting material BN-1 used in the light emitting layer was replaced with BN-2, and a specific device structure was as follows: ITO/HATCN (6nm)/TAPC (30 nm)/TCTA (5nm)/mCP (5nm)/EML (20nm)/TmPyPB (40nm)/LiF (1nm)/Al (100nm), wherein EML represents a light-emitting layer, and the light-emitting layer is composed of a host material mCBP with the mass percentage of 97% and a doped guest light-emitting material BN-2 with the mass percentage of 3%.
The device performance results of the organic electroluminescent device BN-2 prepared in the embodiment are as follows: detailed electroluminescent property data of the device are shown in Table 1, with a spectral peak of 488nm, a half-peak width of 26nm, CIE color coordinate values of (0.14, 0.36), a maximum external quantum efficiency of 27.8%, a maximum power efficiency of 33.1 lm/W and a maximum luminance of 9726cd/m2。
Effect example 3: preparation of organic electroluminescent device BN-3
The same preparation method as that of effect example 1 except that the guest light emitting material BN-1 used in the light emitting layer was replaced with BN-3, and a specific device structure was as follows: ITO/HATCN (6nm)/TAPC (30 nm)/TCTA (5nm)/mCP (5nm)/EML (20nm)/TmPyPB (40nm)/LiF (1nm)/Al (100nm), wherein EML represents a light-emitting layer, and the light-emitting layer is composed of a host material mCBP with the mass percentage of 97% and a doped guest light-emitting material BN-3 with the mass percentage of 3%.
Device characteristics of the organic electroluminescent device BN-3 prepared in this example were measuredThe energy results are as follows: detailed electroluminescent property data of the device are shown in Table 1, with a spectral peak of 496nm, a half-peak width of 30nm, CIE color coordinate values of (0.13, 0.54), a maximum external quantum efficiency of 27.2%, a maximum power efficiency of 50.8 lm/W and a maximum luminance of 11483cd/m2。
Effect example 4: preparation of organic electroluminescent device BN-4
The same preparation method as that of effect example 1 except that the guest light emitting material BN-1 used in the light emitting layer was replaced with BN-4, and a specific device structure was as follows: ITO/HATCN (6nm)/TAPC (30 nm)/TCTA (5nm)/mCP (5nm)/EML (20nm)/TmPyPB (40nm)/LiF (1nm)/Al (100nm), wherein EML represents a light-emitting layer, and the light-emitting layer is composed of a host material mCBP with the mass percentage of 97% and a doped guest light-emitting material BN-4 with the mass percentage of 3%.
The device performance results of the organic electroluminescent device BN-4 prepared in the embodiment are as follows: detailed electroluminescent property data of the device are shown in Table 1, with a spectral peak of 496nm, a half-peak width of 31nm, CIE color coordinate values of (0.15, 0.55), a maximum external quantum efficiency of 25.9%, a maximum power efficiency of 44.7 lm/W and a maximum luminance of 13725cd/m2。
Effect example 5: preparation of organic electroluminescent device BN-5
The same preparation method as that of effect example 1 except that the guest light emitting material BN-1 used in the light emitting layer was replaced with BN-5, and a specific device structure was as follows: ITO/HATCN (6nm)/TAPC (30 nm)/TCTA (5nm)/mCP (5nm)/EML (20nm)/TmPyPB (40nm)/LiF (1nm)/Al (100nm), wherein EML represents a light-emitting layer, and the light-emitting layer is composed of a host material mCBP with the mass percentage of 97% and a doped guest light-emitting material BN-5 with the mass percentage of 3%.
The device performance results of the organic electroluminescent device BN-5 prepared in the embodiment are as follows: detailed electroluminescent property data of the device are shown in Table 1, with a spectral peak of 500nm, a half-peak width of 32nm, CIE color coordinate values of (0.16, 0.56), a maximum external quantum efficiency of 22.9%, a maximum power efficiency of 36.2 lm/W and a maximum luminance of 12848cd/m2。
Effect example 6: preparation of organic electroluminescent device BN-6
The same preparation method as that of effect example 1 except that the guest light emitting material BN-1 used in the light emitting layer was replaced with BN-6, and a specific device structure was as follows: ITO/HATCN (6nm)/TAPC (30 nm)/TCTA (5nm)/mCP (5nm)/EML (20nm)/TmPyPB (40nm)/LiF (1nm)/Al (100nm), wherein EML represents a light-emitting layer, and the light-emitting layer is composed of a host material mCBP with the mass percentage of 97% and a doped guest light-emitting material BN-6 with the mass percentage of 3%.
The device performance results of the organic electroluminescent device BN-6 prepared in the embodiment are as follows: detailed electroluminescent property data of the device are shown in Table 1, with a spectral peak of 496nm, a half-peak width of 31nm, CIE color coordinate values of (0.15, 0.56), a maximum external quantum efficiency of 23.5%, a maximum power efficiency of 34.8 lm/W and a maximum luminance of 11014cd/m2。
Effect example 7: preparation of organic electroluminescent device BN-7
The same preparation method as that of effect example 1 except that the guest light emitting material BN-1 used in the light emitting layer was replaced with BN-7, and a specific device structure was as follows: ITO/HATCN (6nm)/TAPC (30 nm)/TCTA (5nm)/mCP (5nm)/EML (20nm)/TmPyPB (40nm)/LiF (1nm)/Al (100nm), wherein EML represents a light-emitting layer, and the light-emitting layer is composed of a host material mCBP with the mass percentage of 97% and a doped guest light-emitting material BN-7 with the mass percentage of 3%.
The device performance results of the organic electroluminescent device BN-7 prepared in the embodiment are as follows: detailed electroluminescent property data of the device are shown in Table 1, with a spectral peak of 500nm, a half-peak width of 31nm, CIE color coordinate values of (0.14, 0.56), a maximum external quantum efficiency of 25.7%, a maximum power efficiency of 41.0 lm/W and a maximum luminance of 10409cd/m2。
Effect example 8: preparation of organic electroluminescent device BN-8
The same preparation method as that of effect example 1 except that the guest light emitting material BN-1 used in the light emitting layer was replaced with BN-8, and a specific device structure was as follows: ITO/HATCN (6nm)/TAPC (30 nm)/TCTA (5nm)/mCP (5nm)/EML (20nm)/TmPyPB (40nm)/LiF (1nm)/Al (100nm), wherein EML represents a light-emitting layer, and the light-emitting layer is composed of a host material mCBP with the mass percentage of 97% and a doped guest light-emitting material BN-8 with the mass percentage of 3%.
The device performance results of the organic electroluminescent device BN-8 prepared in the embodiment are as follows: detailed electroluminescent property data of the device are shown in Table 1, with a spectral peak of 496nm, a half-peak width of 29nm, CIE color coordinate values of (0.12, 0.53), a maximum external quantum efficiency of 24.2%, a maximum power efficiency of 38.8 lm/W and a maximum luminance of 10827cd/m2。
Effect example 9: preparation of organic electroluminescent device BN-9
The same preparation method as that of effect example 1 except that the guest light emitting material BN-1 used in the light emitting layer was replaced with BN-9, and a specific device structure was as follows: ITO/HATCN (6nm)/TAPC (30 nm)/TCTA (5nm)/mCP (5nm)/EML (20nm)/TmPyPB (40nm)/LiF (1nm)/Al (100nm), wherein EML represents a light-emitting layer, and the light-emitting layer is composed of a host material mCBP with the mass percentage of 97% and a doped guest light-emitting material BN-9 with the mass percentage of 3%.
The device performance results of the organic electroluminescent device BN-9 prepared in the embodiment are as follows: detailed electroluminescent property data of the device are shown in Table 1, with a spectral peak of 496nm, a half-peak width of 30nm, CIE color coordinate values of (0.12, 0.53), a maximum external quantum efficiency of 26.4%, a maximum power efficiency of 47.7 lm/W and a maximum luminance of 11204cd/m2。
Effect example 10: preparation of organic electroluminescent device BN-10
The same preparation method as that of effect example 1 except that the guest light emitting material BN-1 used in the light emitting layer was replaced with BN-10, and a specific device structure was as follows: ITO/HATCN (6nm)/TAPC (30 nm)/TCTA (5nm)/mCP (5nm)/EML (20nm)/TmPyPB (40nm)/LiF (1nm)/Al (100nm), wherein EML represents a light-emitting layer, and the light-emitting layer is composed of a host material mCBP with the mass percentage of 97% and a doped guest light-emitting material BN-10 with the mass percentage of 3%.
The device performance results of the organic electroluminescent device BN-10 prepared in the embodiment are as follows: detailed electroluminescent property data of the devices are shown in Table 1, with spectral peak at 492nm, full width at half maximum at 28nm, CIE color coordinate values of (0.10, 0.46), andthe large external quantum efficiency is 25.8%, the maximum power efficiency is 34.6 lm/W and the maximum luminance is 12055cd/m2。
Effect example 11: preparation of organic electroluminescent device BN-11
The same preparation method as that of effect example 1 except that the guest light emitting material BN-1 used in the light emitting layer was replaced with BN-11, and a specific device structure was as follows: ITO/HATCN (6nm)/TAPC (30 nm)/TCTA (5nm)/mCP (5nm)/EML (20nm)/TmPyPB (40nm)/LiF (1nm)/Al (100nm), wherein EML represents a light-emitting layer, and the light-emitting layer is composed of a host material mCBP with the mass percentage of 97% and a doped guest light-emitting material BN-11 with the mass percentage of 3%.
The device performance results of the organic electroluminescent device BN-11 prepared in this example are as follows: detailed electroluminescent property data of the device are shown in Table 1, with a spectral peak of 492nm, a half-peak width of 30nm, CIE color coordinate values of (0.12, 0.54), a maximum external quantum efficiency of 24.8%, a maximum power efficiency of 32.8 lm/W and a maximum luminance of 10473cd/m2。
Effect example 12: preparation of organic electroluminescent device BN-12
The same preparation method as that of effect example 1 except that the guest light emitting material BN-1 used in the light emitting layer was replaced with BN-12, and a specific device structure was as follows: ITO/HATCN (6nm)/TAPC (30 nm)/TCTA (5nm)/mCP (5nm)/EML (20nm)/TmPyPB (40nm)/LiF (1nm)/Al (100nm), wherein EML represents a light-emitting layer, and the light-emitting layer is composed of a host material mCBP with the mass percentage of 97% and a doped guest light-emitting material BN-12 with the mass percentage of 3%.
The device performance results of the organic electroluminescent device BN-12 prepared in this example are as follows: detailed electroluminescent property data of the device are shown in Table 1, with a spectral peak of 496nm, a half-peak width of 30nm, CIE color coordinate values of (0.13, 0.55), a maximum external quantum efficiency of 25.7%, a maximum power efficiency of 31.2 lm/W and a maximum luminance of 10171cd/m2。
Table 1: effect examples data parameters of electroluminescent devices
Figure BDA0003126832910000191
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 (5)

1. A green light narrow spectrum three-coordination boron luminescent compound containing a carbazole skeleton has a structural formula shown as one of the following formulas:
Figure FDA0003126832900000011
Figure FDA0003126832900000021
2. an organic electroluminescent device comprises a cathode, an anode and a plurality of organic functional layers between the two electrodes, wherein at least one layer of the organic functional layers is a light-emitting layer; the method is characterized in that: the light-emitting layer contains any one of the green-light narrow-spectrum three-coordinate boron light-emitting compounds containing a carbazole skeleton described in claim 1.
3. An organic electroluminescent device as claimed in claim 2, wherein: the organic functional layer other than the light emitting layer is one or more of a hole injection layer, a hole transport layer, an exciton blocking layer, an electron transport layer, and an electron injection layer.
4. An organic electroluminescent device as claimed in claim 2 or 3, wherein: the green light narrow-spectrum three-coordination boron luminescent compound containing the carbazole skeleton as claimed in claim 1 is doped into a host material as a doping material, wherein the host material is mCBP, and the doping mass concentration is 2-5%.
5. An electroluminescent device as claimed in claim 4, characterized in that: the electroluminescent device is used for preparing an organic electroluminescent display or an organic electroluminescent lighting source.
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113896741A (en) * 2021-11-11 2022-01-07 吉林大学 Spiro-structured compounds containing boron-nitrogen coordination bonds and their organic electroluminescent devices as light-emitting layers
CN113980040A (en) * 2021-11-21 2022-01-28 吉林大学 A boron-containing asymmetric spiro compound and its application in organic electroluminescent devices
CN114014881A (en) * 2021-11-10 2022-02-08 深圳大学 A narrow emission high-efficiency multiple resonance light-emitting material and its preparation method and organic light-emitting diode
CN115286649A (en) * 2022-07-20 2022-11-04 广东工业大学 A kind of aryl boron nitrogen compound with narrow band emission and its preparation and application
CN116120349A (en) * 2022-01-28 2023-05-16 季华恒烨(佛山)电子材料有限公司 Boron-nitrogen compound and preparation method and application thereof
CN116120350A (en) * 2022-01-28 2023-05-16 季华恒烨(佛山)电子材料有限公司 Boron-nitrogen compound and preparation method and application thereof

Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103360416A (en) * 2013-07-16 2013-10-23 山西大学 Arylboron compound based on carbazole as well as preparation method and application of arylboron
CN107501311A (en) * 2017-07-14 2017-12-22 瑞声科技（南京）有限公司 Electroluminescent organic material and its luminescent device
CN108530475A (en) * 2016-07-29 2018-09-14 江苏三月光电科技有限公司 A kind of high color purity boracic organic electroluminescent compounds and its application
US20180331302A1 (en) * 2017-03-16 2018-11-15 Wuhan China Star Optoelectronics Technology Co., Ltd. Organic light emitting device and preparation method thereof
CN110386923A (en) * 2018-04-19 2019-10-29 北京鼎材科技有限公司 Carbazole compound and its application and organic electroluminescence device
CN110483574A (en) * 2019-05-15 2019-11-22 苏州大学 Three carbazole derivates of fluorenes spiral shell phenyl, preparation method and application and electronic device
US20190393084A1 (en) * 2018-06-25 2019-12-26 Tokyo Electron Limited Method Utilizing Thermal Decomposition Material To Relax Queue Time Control
CN110627822A (en) * 2019-10-08 2019-12-31 吉林大学 A green-light narrow-spectrum tricoordinate boron luminescent compound, luminescent composition and application thereof
CN110872316A (en) * 2019-11-29 2020-03-10 清华大学 Novel compound, application thereof and organic electroluminescent device using compound
JP2020076138A (en) * 2018-11-09 2020-05-21 日本製鉄株式会社 Non-oriented electrical steel sheet
CN111533762A (en) * 2020-05-29 2020-08-14 上海天马有机发光显示技术有限公司 Boron heterocyclic compound, display panel, and display device
CN111777633A (en) * 2020-08-07 2020-10-16 吉林大学 A boron-containing compound and an organic electroluminescent device containing the same
CN112679310A (en) * 2019-10-18 2021-04-20 罗门哈斯电子材料韩国有限公司 Multiple light emitting materials and organic electroluminescent device comprising the same
CN112930382A (en) * 2018-10-26 2021-06-08 罗门哈斯电子材料韩国有限公司 Multiple light emitting materials and organic electroluminescent device comprising the same

Patent Citations (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103360416A (en) * 2013-07-16 2013-10-23 山西大学 Arylboron compound based on carbazole as well as preparation method and application of arylboron
CN108530475A (en) * 2016-07-29 2018-09-14 江苏三月光电科技有限公司 A kind of high color purity boracic organic electroluminescent compounds and its application
US20180331302A1 (en) * 2017-03-16 2018-11-15 Wuhan China Star Optoelectronics Technology Co., Ltd. Organic light emitting device and preparation method thereof
CN107501311A (en) * 2017-07-14 2017-12-22 瑞声科技（南京）有限公司 Electroluminescent organic material and its luminescent device
CN110386923A (en) * 2018-04-19 2019-10-29 北京鼎材科技有限公司 Carbazole compound and its application and organic electroluminescence device
US20190393084A1 (en) * 2018-06-25 2019-12-26 Tokyo Electron Limited Method Utilizing Thermal Decomposition Material To Relax Queue Time Control
CN112930382A (en) * 2018-10-26 2021-06-08 罗门哈斯电子材料韩国有限公司 Multiple light emitting materials and organic electroluminescent device comprising the same
JP2020076138A (en) * 2018-11-09 2020-05-21 日本製鉄株式会社 Non-oriented electrical steel sheet
CN110483574A (en) * 2019-05-15 2019-11-22 苏州大学 Three carbazole derivates of fluorenes spiral shell phenyl, preparation method and application and electronic device
CN110627822A (en) * 2019-10-08 2019-12-31 吉林大学 A green-light narrow-spectrum tricoordinate boron luminescent compound, luminescent composition and application thereof
CN112679310A (en) * 2019-10-18 2021-04-20 罗门哈斯电子材料韩国有限公司 Multiple light emitting materials and organic electroluminescent device comprising the same
CN110872316A (en) * 2019-11-29 2020-03-10 清华大学 Novel compound, application thereof and organic electroluminescent device using compound
CN111533762A (en) * 2020-05-29 2020-08-14 上海天马有机发光显示技术有限公司 Boron heterocyclic compound, display panel, and display device
CN111777633A (en) * 2020-08-07 2020-10-16 吉林大学 A boron-containing compound and an organic electroluminescent device containing the same

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
YINCAI XU，等: "Attaching strong auxiliary acceptor onto B-N-containing multiple resonance framework and achieving highly efficient electroluminescence with ultrahigh color purity", 《CHEMRXIV》 *
YUEWEI ZHANG，等: "Multi-Resonance Induced Thermally Activated Delayed Fluorophores for Narrowband Green OLEDs", 《ANGEWANDTE CHEMIE INTERNATIONAL EDITION》 *
越柏玲，等: "聚集诱导发光分子的光电功能与器件应用", 《中国科学:化学》 *
陈斌，等: "多功能聚集诱导发光OLED材料研究进展", 《科学通报》 *

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114014881A (en) * 2021-11-10 2022-02-08 深圳大学 A narrow emission high-efficiency multiple resonance light-emitting material and its preparation method and organic light-emitting diode
CN114014881B (en) * 2021-11-10 2024-01-12 深圳大学 Narrow-emission efficient multi-resonance luminescent material, preparation method thereof and organic light-emitting diode
CN113896741A (en) * 2021-11-11 2022-01-07 吉林大学 Spiro-structured compounds containing boron-nitrogen coordination bonds and their organic electroluminescent devices as light-emitting layers
CN113896741B (en) * 2021-11-11 2024-01-19 吉林大学 Spiro structure compound containing boron-nitrogen coordination bond and organic electroluminescent device using same as light-emitting layer
CN113980040A (en) * 2021-11-21 2022-01-28 吉林大学 A boron-containing asymmetric spiro compound and its application in organic electroluminescent devices
CN113980040B (en) * 2021-11-21 2024-02-27 吉林大学 Boron-containing asymmetric spiro compound and application thereof in organic electroluminescent device
CN116120349A (en) * 2022-01-28 2023-05-16 季华恒烨(佛山)电子材料有限公司 Boron-nitrogen compound and preparation method and application thereof
CN116120350A (en) * 2022-01-28 2023-05-16 季华恒烨(佛山)电子材料有限公司 Boron-nitrogen compound and preparation method and application thereof
WO2023142486A1 (en) * 2022-01-28 2023-08-03 季华恒烨(佛山)电子材料有限公司 Boron-nitrogen compound, preparation method therefor, and application thereof
WO2023142485A1 (en) * 2022-01-28 2023-08-03 季华恒烨(佛山)电子材料有限公司 Boron-nitrogen compound, preparation method therefor, and application thereof
CN115286649A (en) * 2022-07-20 2022-11-04 广东工业大学 A kind of aryl boron nitrogen compound with narrow band emission and its preparation and application

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