WO2023273357A1 - 一种含有咔唑的化合物及有机电致发光器件 - Google Patents
一种含有咔唑的化合物及有机电致发光器件 Download PDFInfo
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- WO2023273357A1 WO2023273357A1 PCT/CN2022/076054 CN2022076054W WO2023273357A1 WO 2023273357 A1 WO2023273357 A1 WO 2023273357A1 CN 2022076054 W CN2022076054 W CN 2022076054W WO 2023273357 A1 WO2023273357 A1 WO 2023273357A1
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- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Definitions
- the invention relates to the technical field of organic electroluminescence, in particular to a compound containing carbazole and an organic electroluminescence device.
- OLED Organic electroluminescent device
- the organic plastic layer of OLED is thinner, lighter and more flexible;
- the light-emitting layer of OLED is relatively light, so its base layer can use flexible materials instead of rigid materials.
- OLED base layer is made of plastic material, while LED and LCD use glass base layer;
- OLED is a current-type organic light-emitting device, which is a phenomenon of luminescence caused by injection and recombination of carriers, and the luminous intensity is proportional to the injected current.
- the holes generated by the anode and the electrons generated by the cathode will move, inject into the hole transport layer and the electron transport layer respectively, and migrate to the light emitting layer.
- energy excitons are generated, which excite light-emitting molecules and finally produce visible light.
- the materials that constitute the organic layer in the device such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, electron injection materials, etc., are backed by stable and effective materials. , so there is a continuous demand for the development of new materials.
- the present invention provides a compound containing carbazole and an organic electroluminescent device.
- R1-R2 are each independently hydrogen, deuterium, deuterated or undeuterated phenyl, deuterated or undeuterated biphenyl;
- L is a single bond, phenyl, naphthyl
- R3 is a deuterated C3-C20 cycloalkyl group, a deuterated C6-C20 aromatic group
- p and n are 0, 1, 2, 3, 4 each independently.
- the R3 is selected from deuterated phenyl, deuterated naphthyl, deuterated phenanthrenyl, deuterated C3-C12 cycloalkyl groups;
- the L is connected to the No. 1 position of dibenzofuran, and R1-R2 are each independently hydrogen, deuterium, deuterated or undeuterated phenyl.
- R3 is selected from one of the following groups:
- An organic electroluminescent device comprising a first electrode, a second electrode and an organic layer formed between the first electrode and the second electrode, the organic layer containing the compound above.
- the organic layer comprises a hole injection layer, a first hole transport layer, a second hole transport layer, a light-emitting layer, a hole blocking layer, an electron transport layer, and an electron injection layer; the hole injection layer, At least one of the first hole transport layer, the second hole transport layer, the light emitting layer, the hole blocking layer, the electron transport layer, and the electron injection layer contains the compound described above.
- the above-mentioned compounds are contained in the light-emitting layer.
- the light-emitting layer also contains at least one of the following compounds G1-G56:
- An electronic display device containing the above-mentioned organic electroluminescence device.
- An OLED lighting device containing the above-mentioned organic electroluminescent device.
- the room temperature in the present invention is 25 ⁇ 5°C.
- the present invention designs a compound used as an organic electroluminescent material, which has the following characteristics:
- the organic electroluminescent material of the present invention introduces deuterium (deuterium) into traditional organic materials of this type, and the introduction of deuterium
- the phase solubility between this type of material and the dopant material is improved, the stability of the interface is improved, and the luminous efficiency and stability of the device are greatly improved.
- the combination further improves the lifespan and luminous efficiency of the device.
- deuterium can lead to the weakening of the vibration in the material molecule, thereby reducing the occurrence of non-radiative transitions, improving the internal quantum efficiency of the material, and improving the stability of the device, thereby improving the luminous efficiency and life of the device, and the deuterium
- the introduction can adjust the molecular weight of the material, adjust its evaporation temperature, make it better match with the electron-donating group material, and improve the stability and life of the device.
- there are two carbazoles in the material molecule and the carbazole group has a higher triplet energy level, resulting in the compound of the present invention having a higher triplet energy level, which effectively prevents the energy from doping the material to The reverse transmission of the host material improves the luminous efficiency of the device.
- the organic electroluminescent device prepared by using the designed compound of the invention has better luminous efficiency and lifetime.
- FIG. 1 is a schematic structural view of an organic electroluminescent device of the present invention.
- Fig. 2 is an HPLC chart of compound 1 prepared in Example 1 of the present invention.
- Fig. 3 is the DSC spectrum of compound 1 prepared in Example 1 of the present invention. It can be seen from Fig. 3 that the Tm value of compound 1 is 304.33°C.
- Fig. 4 is the TGA spectrum of compound 1 prepared in Example 1 of the present invention. It can be seen from Fig. 4 that the thermal weight loss temperature Td is 477.67°C.
- Fig. 5 is the lifetime figure of organic electroluminescent device in application example 1 of the present invention and comparative example 1; As can be seen from Fig. 5, the T97% lifetime of the organic electroluminescent device prepared by application example 1 of the present invention and comparative example 1 is respectively 621h and 454h.
- substituted refers to the rearrangement of at least one hydrogen in the group with a hydrocarbyl, hydrocarbyl derivative, halogen or cyano (-CN) bit.
- unsubstituted means that at least one hydrogen in the group does not recoordinate with a hydrocarbyl, hydrocarbyl derivative, halogen or cyano group (-CN).
- hydrocarbyl or hydrocarbon derivative groups may include C1 to C20 alkyl, C2 to C20 alkenyl, C2 to C20 alkynyl, C6 to C20 aryl, C5 to C20 heteroaryl, C1 to C20 alkylamino, C6 to C20 C20 arylamino, C6 to C20 heteroarylamino, C6 to C20 arylheteroarylamino, etc., but not limited thereto.
- compound 1-a (1eq, 10g, 445.9g/mol, 22.43mmol), compound 1-b (1.1eq, 9.26g, 375.28g/mol, 24.67mmol) were dissolved in 200mL toluene, and acetic acid was added Palladium (0.25g, 224.51g/mol, 1.12mmol), X-phos (0.26g, 476.72g/mol, 1.12mmol), potassium carbonate (9.30g, 138.21g/mol, 67.28mmol), then add 100mL ethanol and 50mL of water was stirred overnight at 82°C, and the reaction progress was monitored by HPLC.
- the preparation method is basically the same as in Example 1, the difference is that compound 1-b is replaced by compound 2-b to obtain the final target product compound 2 with a yield of 41.5%, ESI-MS (m/z) (M+): theoretical value 710.83, measured value 711.34, elemental analysis results (molecular formula C49H22D7N5O): theoretical value C, 82.79; H, 5.10; N, 9.85; O, 2.25; measured value C, 82.73; H, 5.17; N, 9.80;
- the preparation method is basically the same as in Example 1, the difference is that compound 1-b is replaced by compound 3-b to obtain the final target product compound 3 with a yield of 45.6%, ESI-MS (m/z) (M+): theoretical value 710.83, measured value 711.21, element analysis result (molecular formula C49H22D7N5O): theoretical value C, 82.79; H, 5.10; N, 9.85; O, 2.25; measured value C, 82.83; H, 5.06; N, 9.89; O, 2.22.
- the preparation method is basically the same as in Example 1, except that compound 1-a is replaced by compound 4-a to obtain the final target product compound 8 with a yield of 51.6%, ESI-MS (m/z) (M+): theoretical value 666.81, measured value 667.25, elemental analysis result (molecular formula C45H14D13N5O): theoretical value C, 81.05; H, 6.04; N, 10.50; O, 2.40; measured value C, 81.09; H, 6.00; N, 10.57;
- the synthetic method of compound 10 is as follows:
- the preparation method is basically the same as in Example 1, except that compound 1-b is replaced by compound 5-b to obtain the final target product compound 10 with a yield of 44.7%, ESI-MS (m/z) (M+): theoretical value 784.91, measured value 783.98, elemental analysis results (molecular formula C55H28D5N5O): theoretical value C, 84.16; H, 4.88; N, 8.92; O, 2.04; measured value C, 84.10; H, 4.94; N, 8.90;
- Embodiment 6 is a diagrammatic representation of Embodiment 6
- the preparation method is basically the same as in Example 1, the difference is that compound 1-b is replaced by compound 6-b to obtain the final target product compound 18 with a yield of 38.5%, ESI-MS (m/z) (M+): theoretical value 786.93 , measured value 787.83, elemental analysis results (molecular formula C55H26D7N5O): theoretical value C, 83.95; H, 5.12; N, 8.90; O, 2.03; measured value C, 83.97; H, 5.10; N, 8.84;
- Embodiment 7 is a diagrammatic representation of Embodiment 7:
- the synthetic method of compound 24 is as follows:
- the preparation method is basically the same as in Example 1, the difference is that compound 1-b is replaced by compound 7-b to obtain the final target product compound 24 with a yield of 40.8%, ESI-MS (m/z) (M+): theoretical value 786.93, measured value 787.35, element analysis results (molecular formula C55H26D7N5O): theoretical value C, 83.95; H, 5.12; N, 8.90; O, 2.03; measured value C, 83.99; H, 5.08; N, 8.85; O, 2.08.
- Embodiment 8 is a diagrammatic representation of Embodiment 8
- the synthetic method of compound 32 is as follows:
- the preparation method is basically the same as in Example 1, the difference is that compound 1-a is replaced by compound 8-a to obtain the final target product compound 32 with a yield of 50.8%, ESI-MS (m/z) (M+): theoretical value 734.86, measured value 735.60, elemental analysis results (molecular formula C51H26D5N5O): theoretical value C, 83.36; H, 4.94; N, 9.53; O, 2.18; measured value C, 83.30; H, 4.99; N, 9.53; O, 2.18.
- Embodiment 9 is a diagrammatic representation of Embodiment 9:
- the preparation method is basically the same as in Example 1, the difference is that compound 1-a is replaced by compound 9-a, compound 1-b is replaced by compound 9-b, and the final target product compound 34 is obtained, with a yield of 37.4%, ESI-MS (m/z)(M+): theoretical value 786.93, measured value 787.19, elemental analysis result (molecular formula C55H26D7N5O): theoretical value C, 83.95; H, 5.12; N, 8.90; O, 2.03; measured value C, 83.98; H , 5.16; N, 8.86; O, 2.00.
- the preparation method is basically the same as in Example 1, the difference is that compound 1-a is replaced by compound 10-a, compound 1-b is replaced by compound 10-b, and the final target product compound 41 is obtained with a yield of 35.8%, ESI-MS (m/z)(M+): theoretical value 861.01, measured value 861.55, element analysis result (molecular formula C61H32D5N5O): theoretical value C, 85.09; H, 4.92; N, 8.13; O, 1.86; measured value C, 85.04; H , 4.97; N, 8.17; O, 1.82.
- the synthetic method of compound 65 is as follows:
- the preparation method is basically the same as in Example 1, the difference is that compound 1-a is replaced by compound 11-a to obtain the final target product compound 65 with a yield of 48.9%, ESI-MS (m/z) (M+): theoretical value 734.86, measured value 735.41, element analysis results (molecular formula C51H26D5N5O): theoretical value C, 83.36; H, 4.94; N, 9.53; O, 2.18; measured value C, 83.30; H, 5.00; N, 9.56; O, 2.14.
- the preparation method is basically the same as in Example 1, the difference is that compound 1-a is replaced by compound 12-a to obtain the final target product compound 66 with a yield of 50.6%, ESI-MS (m/z) (M+): theoretical value 734.86, measured value 735.22, elemental analysis results (molecular formula C51H26D5N5O): theoretical value C, 83.36; H, 4.94; N, 9.53; O, 2.18; measured value C, 83.39; H, 4.91; N, 9.58; O, 2.12.
- thermogravimetric temperature Td is the temperature at which the weight loss is 5% in a nitrogen atmosphere. It is measured on a TGA N-1000 thermogravimetric analyzer. During the measurement, the nitrogen flow rate is 10mL/min. Xinke DSC N-650) measurement, heating rate 10 °C / min.
- Example 01 1 477.67 304.33
- Example 02 2 463.41 317.52
- Example 03 3 492.50 277.18
- Example 04 8 485.71 328.41
- Example 05 10 511.65 262.56
- Example 06 18 475.26 235.35
- Example 07 twenty four 503.22 289.49
- Example 08 32 524.58 309.58
- Example 09 34 460.46 247.17
- Example 10 41 478.34 303.44
- Example 11 65 484.62 265.06
- Example 12 66 508.07 317.48
- the compound synthesized by the present invention has excellent thermal stability, indicating that the compounds conforming to the general structural formula of the present invention have excellent thermal stability and can meet the requirements for the use of organic electroluminescent materials.
- ITO is used as the anode substrate material of the reflective layer, and its surface is treated with water, acetone, and N2 plasma in sequence;
- HIL hole injection layer
- HIL hole injection layer
- HTL first hole transport layer
- the compound 1 and G1 designed in the present invention are co-evaporated as the green light host material according to the mass ratio of 5:5, and GD-1 is used as the dopant material (the amount of GD-1 is 8% of the total mass of compound 1 and G1).
- HBL hole blocking layer
- ET-1 and LiQ are co-evaporated on the hole blocking layer (HBL) according to the ratio of 5:5 to obtain an electron transport layer (ETL) with a thickness of 30nm;
- silver (Ag) is vapor-deposited on the electron injection layer to form a cathode with a thickness of 100nm, and DNTPD with a thickness of 50nm is deposited on the above-mentioned cathode sealing layer.
- a UV-curable adhesive and a packaging film containing a desiccant are used on the surface of the cathode. (seal cap) is sealed to protect the organic electroluminescent device from being affected by oxygen or moisture in the atmosphere. So far, the organic electroluminescent device is prepared.
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Abstract
本发明公开了一种含有咔唑的化合物及有机电致发光器件，化合物以特定的方式将两个咔唑、三嗪、以及二苯并呋喃连接而成。且在传统的该类有机材料中引入重氢(氘)，氘的引入提高了该类材料与掺杂材料的相溶解性，提高界面稳定性，进而大幅度提高了器件的发光效率及稳定性，同时氘代的引入使得该类化合物能够更好的与掺杂材料进行搭配，进一步提高了器件的寿命及发光效率。
Description
本发明涉及有机电致发光技术领域，具体涉及一种含有咔唑的化合物及有机电致发光器件。
有机电致发光器件(OLED)是近年来国际上平板显示领域的一个研究热点。相较于LCD具有以下优点
相较于LED(发光二极管)或LCD(液晶显示)的晶体层，OLED的有机塑料层更薄、更轻而且更富于柔韧性；
OLED的发光层比较轻，因此它的基层可使用富于柔韧性的材料，而不会使用刚性材料，OLED基层为塑料材质，而LED和LCD则使用玻璃基层；
OLED属于一种电流型的有机发光器件，是通过载流子的注入和复合而致发光的现象，发光强度与注入的电流成正比。OLED在电场的作用下，阳极产生的空穴和阴极产生的电子就会发生移动，分别向空穴传输层和电子传输层注入，迁移到发光层。当二者在发光层相遇时，产生能量激子，从而激发发光分子最终产生可见光。
由于OLED的外量子效率与内量子效率之间存在巨大的差距，极大的制约了OLED的发展，因此，如何提高OLED的光取出效率也成为研究的热点。ITO薄膜和玻璃衬底的界面以及玻璃衬底与空气的界面处会发生全反射，出射到OLED器件前向外部空间的光约占有机材料薄膜EL总量的20％，其余约80％的光主要以导波形式限制在有机材料薄膜、ITO薄膜和玻璃衬底中，严重制约了OLED的发展与应用，如何减少OLED器件中的全反射效应、提高光耦合到器件前向外部空间的比例引，进而提高器件的性能起了人们的广泛关注。
为了充分发挥有机发光器件具有的优异的特征，构成器件内有机物层的材料，例如空穴注入材料、空穴传输材料、发光材料、电子传输材料、电子注入材料等以稳定且有效的材料为后盾，因此持续要求开发新的材料。
发明内容
发明目的：针对上述技术问题，本发明提供了一种含有咔唑的化合物及有机电致发光器件。
为了达到上述发明目的，本发明所采用的技术方案如下：
一种含有咔唑的化合物，其特征在于，其结构式如下所示基团：
R1-R2各自独立的为氢、氘、氘代或未氘代的苯基、氘代或未氘代的联苯基；
L为单键、苯基、萘基；
R3为经氘代的C3-C20的环烷基团、经氘代的C6-C20芳香族基团；
p、n各自独立的为0、1、2、3、4。
优选的，所述R3选自经氘代苯基、经氘代的萘基、经氘代的菲基、经氘代的C3-C12的环烷基团；
所述L连接于二苯并呋喃的1号位，R1-R2各自独立的为氢、氘、氘代或未氘代的苯基。
进一步地，所述R3选自以下基团之一：
进一步地，其为以下化合物的任意一种：
一种有机电致发光器件，包括第一电极、第二电极以及在所述第一电极和所述第二电极 之间形成的有机层，所述有机层中含有上述化合物。
进一步地，所述有机层包含空穴注入层、第一空穴传输层、第二空穴传输层、发光层、空穴阻挡层、电子传输层、电子注入层；所述空穴注入层、第一空穴传输层、第二空穴传输层、发光层、空穴阻挡层、电子传输层、电子注入层中的至少一层含有上述化合物。
进一步地，所述发光层中含有上述的化合物。
更进一步，所述发光层中还含有以下化合物G1-G56中的至少一种：
一种含有上述有机电致发光器件的电子显示设备。
一种含有上述有机电致发光器件的OLED照明设备。
本发明所述室温均为25±5℃。
本发明的有益效果：
本发明设计了一款作为有机电致发光材料使用的化合物，具备一下特征：其一，本发明的有机电致发光才材料在传统的该类有机材料中引入重氢(氘)，氘的引入提高了该类材料与掺杂材料的相溶解性，提高界面稳定性，进而大幅度提高了器件的发光效率及稳定性，同时氘代的引入使得该类化合物能够更好的与掺杂材料进行搭配，进一步提高了器件的寿命及发光效率。其二，氘代可导致材料分子内振动的减弱，进而降低无辐射跃迁的发生，提高材料的内部量子效率，同时提高了器件的稳定性，进而提高器件的发光效率及寿命，并且氘代的引入能够调节材料的分子量，调整其蒸发温度，使得其更好的与供电子基团材料进行搭配，提高器件的稳定性及寿命。其三，材料分子中具备两个咔唑，咔唑基团具有较高的三线态能级，导致本发明的化合物具有较高的三线态能级，该特性有效避免了能量由掺杂材料到主体材料的反向传递，进而提高了器件的发光效率。
经器件验证，使用本发明设计的化合物制备的有机电致发光器件具有更好的发光效率及寿命。
图1为本发明有机电致发光器件的结构示意图。
图中标号分别代表：
1-阳极、2-空穴注入层、3-第一空穴传输层、4-第二空穴传输层、5-发光层、6-空穴阻挡层、7-电子传输层、8-电子注入层、9-阴极。
图2为本发明实施例1中所制备的化合物1的HPLC图。
图3为本发明实施例1中所制备的化合物1的DSC图谱，由图3可知，化合物1的Tm值为304.33℃。
图4为本发明实施例1中所制备的化合物1的TGA图谱，由图4可知，热失重温度Td值为477.67℃。
图5为本发明应用例1和对照例1中有机电致发光器件的寿命图；由图5可知，本发明应用例1和对照例1所制备的有机电致发光器件的T97％寿命分别为621h和454h。
以下进一步说明和描述了各个方面的实施例。应当理解，本文的描述并非旨在将权利要求书限制于所描述的特定方面。相反，旨在覆盖可包括在由所附权利要求书限定的本公开的精神和范围内的替代、修改和等同物。
如本文所用，在“取代的”或“未取代的”中，术语“取代的”是指该基团中的至少一个氢与 烃基、烃衍生物基、卤素或氰基(-CN)重新配位。术语“未取代的”是指该基团中的至少一个氢不与烃基、烃衍生物基、卤素或氰基(-CN)重新配位。烃基或烃衍生物基团的实例可包括C1至C20烷基、C2至C20烯基、C2至C20炔基、C6至C20芳基、C5至C20杂芳基、C1至C20烷氨基、C6至C20芳氨基、C6至C20杂芳氨基、C6至C20芳基杂芳氨基等，但不限于此。
实施例中未注明具体条件者，按照常规条件或制造商建议的条件进行。所用试剂或仪器未注明生产厂商者，均为可以通过市售购买获得的常规产品。
实施例1：
化合物1的合成方法如下：
氮气保护下，将化合物1-a(1eq，10g，445.9g/mol，22.43mmol)、化合物1-b(1.1eq，9.26g，375.28g/mol，24.67mmol)溶于200mL甲苯中，加入醋酸钯(0.25g，224.51g/mol，1.12mmol)，X-phos(0.26g，476.72g/mol，1.12mmol)，碳酸钾(9.30g，138.21g/mol，67.28mmol)，再加入100mL乙醇和50mL水，82℃下搅拌过夜反应，HPLC监测反应进度。
HPLC监测化合物1-a反应完全后，停止反应，将反应液冷却至室温，加水60mL，搅拌20min，抽滤得滤饼，滤饼使用水和乙醇淋洗2次后真空80℃干燥6小时，将经过干燥的滤饼加入到250mL三口烧瓶中，加入100mL邻二氯苯，加热至120℃是固体完全溶解，溶解完全后趁热过硅胶和活性炭漏斗得滤液，滤液自然降至室温，有白色固体析出后，抽滤得滤饼，滤饼再进行两次重结晶操作后，得最终目标产物化合物1(6.38g，9.69mmol，收率43.2％)，ESI-MS(m/z)(M+)：理论值658.76，实测值659.22，元素分析结果(分子式C45H22D5N5O)：理论值C,82.05；H,4.89；N,10.63；O,2.43；实测值C,82.09；H,4.85；N, 10.67；O,2.39。
实施例2：
化合物2的合成方法如下：
制备方法与实施例1基本相同，区别在于，将化合物1-b替换为化合物2-b，得最终目标产物化合物2，收率41.5％，ESI-MS(m/z)(M+)：理论值710.83，实测值711.34，元素分析结果(分子式C49H22D7N5O)：理论值C,82.79；H,5.10；N,9.85；O,2.25；实测值C,82.73；H,5.17；N,9.80；O,2.30。
实施例3：
化合物3的合成方法如下：
制备方法与实施例1基本相同，区别在于，将化合物1-b替换为化合物3-b，得最终目标产物化合物3，收率45.6％，ESI-MS(m/z)(M+)：理论值710.83，实测值711.21，元素 分析结果(分子式C49H22D7N5O)：理论值C,82.79；H,5.10；N,9.85；O,2.25；实测值C,82.83；H,5.06；N,9.89；O,2.22。
实施例4：
化合物8的合成方法如下：
制备方法与实施例1基本相同，区别在于，将化合物1-a替换为化合物4-a，得最终目标产物化合物8，收率51.6％，ESI-MS(m/z)(M+)：理论值666.81，实测值667.25，元素分析结果(分子式C45H14D13N5O)：理论值C,81.05；H,6.04；N,10.50；O,2.40；实测值C,81.09；H,6.00；N,10.57；O,2.34。
实施例5：
化合物10的合成方法如下：
制备方法与实施例1基本相同，区别在于，将化合物1-b替换为化合物5-b，得最终目标产物化合物10，收率44.7％，ESI-MS(m/z)(M+)：理论值784.91，实测值783.98，元素分析结果(分子式C55H28D5N5O)：理论值C,84.16；H,4.88；N,8.92；O,2.04；实测值C,84.10；H,4.94；N,8.90；O,2.06。
实施例6：
化合物18的合成方法如下：
制备方法与实施例1基本相同，区别在于，将化合物1-b替换为化合物6-b，得最终目标产物化合物18收率38.5％，ESI-MS(m/z)(M+)：理论值786.93，实测值787.83，元素分析结果(分子式C55H26D7N5O)：理论值C,83.95；H,5.12；N,8.90；O,2.03；实测值C,83.97；H,5.10；N,8.84；O,2.09。
实施例7：
化合物24的合成方法如下：
制备方法与实施例1基本相同，区别在于，将化合物1-b替换为化合物7-b，得最终目标产物化合物24，收率40.8％，ESI-MS(m/z)(M+)：理论值786.93，实测值787.35，元素分析结果(分子式C55H26D7N5O)：理论值C,83.95；H,5.12；N,8.90；O,2.03；实测值C,83.99；H,5.08；N,8.85；O,2.08。
实施例8：
化合物32的合成方法如下：
制备方法与实施例1基本相同，区别在于，将化合物1-a替换为化合物8-a，得最终目标产物化合物32，收率50.8％，ESI-MS(m/z)(M+)：理论值734.86，实测值735.60，元素分析结果(分子式C51H26D5N5O)：理论值C,83.36；H,4.94；N,9.53；O,2.18；实测值C,83.30；H,4.99；N,9.53；O,2.18。
实施例9：
化合物34的合成方法如下：
制备方法与实施例1基本相同，区别在于，将化合物1-a替换为化合物9-a，化合物1-b替换为化合物9-b，得最终目标产物化合物34,收率37.4％，ESI-MS(m/z)(M+)：理论值786.93，实测值787.19，元素分析结果(分子式C55H26D7N5O)：理论值C,83.95；H,5.12；N,8.90；O,2.03；实测值C,83.98；H,5.16；N,8.86；O,2.00。
实施例10：
化合物41的合成方法如下：
制备方法与实施例1基本相同，区别在于，将化合物1-a替换为化合物10-a，化合物1-b替换为化合物10-b，得最终目标产物化合物41，收率35.8％，ESI-MS(m/z)(M+)：理论值861.01，实测值861.55，元素分析结果(分子式C61H32D5N5O)：理论值C,85.09；H,4.92；N,8.13；O,1.86；实测值C,85.04；H,4.97；N,8.17；O,1.82。
实施例11：
化合物65的合成方法如下：
制备方法与实施例1基本相同，区别在于，将化合物1-a替换为化合物11-a，得最终目标产物化合物65，收率48.9％，ESI-MS(m/z)(M+)：理论值734.86，实测值735.41，元素分析结果(分子式C51H26D5N5O)：理论值C,83.36；H,4.94；N,9.53；O,2.18；实测值C,83.30；H,5.00；N,9.56；O,2.14。
实施例12：
化合物66的合成方法如下：
制备方法与实施例1基本相同，区别在于，将化合物1-a替换为化合物12-a，得最终目标产物化合物66，收率50.6％，ESI-MS(m/z)(M+)：理论值734.86，实测值735.22，元素 分析结果(分子式C51H26D5N5O)：理论值C,83.36；H,4.94；N,9.53；O,2.18；实测值C,83.39；H,4.91；N,9.58；O,2.12。
材料性质测试：
测试本发明化合物1、2、3、8、10、18、24、32、34、41、65、66的热失重温度Td和熔点Tm，测试结果如下表1所示。
注：热失重温度Td是在氮气气氛中失重5％的温度，在TGA N-1000热重分析仪上进行测定，测定时氮气流量为10mL/min，熔点Tm由示差扫描量热法(DSC，新科DSC N-650)测定，升温速率10℃/min。
表1：
| 项目 | 材料 | Td/℃ | Tm/℃ |
| 实施例01 | 1 | 477.67 | 304.33 |
| 实施例02 | 2 | 463.41 | 317.52 |
| 实施例03 | 3 | 492.50 | 277.18 |
| 实施例04 | 8 | 485.71 | 328.41 |
| 实施例05 | 10 | 511.65 | 262.56 |
| 实施例06 | 18 | 475.26 | 235.35 |
| 实施例07 | 24 | 503.22 | 289.49 |
| 实施例08 | 32 | 524.58 | 309.58 |
| 实施例09 | 34 | 460.46 | 247.17 |
| 实施例10 | 41 | 478.34 | 303.44 |
| 实施例11 | 65 | 484.62 | 265.06 |
| 实施例12 | 66 | 508.07 | 317.48 |
由上述数据可知，本发明所合成的化合物的热稳定性优良，说明符合本发明结构通式的化合物都具有优良的热稳定性，可以满足有机电致发光材料使用的要求。
器件性能测试：
应用例1:
采用ITO作为反射层阳极基板材料，并依次用水、丙酮、N
2等离子对其进行表面处理；
在ITO阳极基板上方，沉积10nm掺杂有5％HAT-CN的HT-1，形成空穴注入层(HIL)；
在空穴注入层(HIL)上方蒸镀100nm的HT-1形成第一空穴传输层(HTL)；
在第一空穴传输层(HTL)上方真空蒸镀GP，形成厚度为30nm的第二空穴传输层(GPL)；
将本发明设计的化合物1与G1按照5:5的质量比例作为绿光主体材料进行共同蒸镀，GD-1作为掺杂材料(GD-1用量为化合物1与G1总质量的8％)蒸镀在第二空穴传输层(GPL)上形成厚度为30nm的发光层；
将HB-1蒸镀到发光层上得到厚度为20nm的空穴阻挡层(HBL)；
将ET-1与LiQ按照5:5的比例进行共同蒸镀到空穴阻挡层(HBL)上得到厚度为30nm的电子传输层(ETL)；
将镁(Mg)和银(Ag)以9:1的比例混合蒸镀到电子传输层(ETL)上方，形成厚度为50nm的电子注入层(EIL)；
此后将银(Ag)蒸镀到电子注入层上方，形成厚度为100nm的阴极，在上述阴极封口层上沉积50nm厚度的DNTPD，此外，在阴极表面以UV硬化胶合剂和含有除湿剂的封装薄膜(seal cap)进行密封，以保护有机电致发光器件不被大气中的氧气或水分所影响至此制备获得有机电致发光器件。
应用例2-12
分别以本发明实施例2-12中的化合物2、3、8、10、18、24、32、34、41、65、66代替化合物1作为绿光主体材料，其他部分与应用例1一致，据此制作出应用例2-12的有机电致发光器件。
对照例1-3：
与应用例1的区别在于，分别用CN112079824A中的GH-1、GH-2、GH-3代替化合物1作为绿光主体材料，其余与应用例1相同。
上述应用例制造的有机电致发光器件及对照例制造的有机电致发光器件的特性是在电流密度为10mA/cm
2的条件下测定的，结果如表2所示。
表2：
由如上表2可知，本发明化合物应用于有机电致发光器件中，在相同电流密度下，发光效率得到了较大幅度的提升，器件的启动电压有所下降，器件的功耗相对降低，使得器件的寿命相应提高。
分别将对照例1-3、应用例1-5所制备的有机电致发光器件进行发光寿命测试，得到发光寿命T97％数据(发光亮度降低至初始亮度97％的时间)，测试设备为TEO发光器件寿命测试系统。结果如表3所示：
表3：
由上表3可知，将本发明化合物应用于有机电致发光器件中，在相同电流密度下，使用寿命得到较大程度提升，具有广阔的应用前景。
Claims (10)
- 一种含有咔唑的化合物，其特征在于，其结构式如下所示基团：
R1-R2各自独立的为氢、氘、氘代或未氘代的苯基、氘代或未氘代的联苯基；L为单键、苯基、萘基；R3为经氘代的C3-C20的环烷基团、经氘代的C6-C20芳香族基团；p、n各自独立的为0、1、2、3、4。 - 如权利要求1所述的有机化合物，其特征在于，所述R3选自经氘代苯基、经氘代的萘基、经氘代的菲基、经氘代的C3-C12的环烷基团；所述L连接于二苯并呋喃的1号位，R1-R2各自独立的为氢、氘、氘代或未氘代的苯基。
- 如权利要求2所述的有机化合物，其特征在于，所述R3选自以下基团之一：
- 如权利要求1所述的有机化合物，其特征在于，其为以下化合物的任意一种：
- 一种有机电致发光器件，其特征在于，包括第一电极、第二电极以及在所述第一电 极和所述第二电极之间形成的有机层，所述有机层中含有如权利要求1-4中任一项所述的化合物。
- 如权利要求5所述的有机电致发光器件，其特征在于，所述有机层包含空穴注入层、第一空穴传输层、第二空穴传输层、发光层、空穴阻挡层、电子传输层、电子注入层；所述空穴注入层、第一空穴传输层、第二空穴传输层、发光层、空穴阻挡层、电子传输层、电子注入层中的至少一层含有权利要求1-4中任一项所述的化合物。
- 如权利要求6所述的有机电致发光器件，其特征在于，所述发光层中含有如权利要求1-4中任一项所述的化合物。
- 如权利要求7所述的有机电致发光器件，其特征在于，所述发光层中还含有以下化合物G1-G56中的至少一种：
- 一种电子显示设备，其特征在于，含有如权利要求7所述的有机电致发光器件。
- 一种OLED照明设备，其特征在于，含有如权利要求7所述的有机电致发光器件。
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| CN110869364A (zh) * | 2017-07-04 | 2020-03-06 | 株式会社斗山 | 有机化合物及利用其的有机电致发光元件 |
| CN112028883A (zh) * | 2020-09-02 | 2020-12-04 | 南京高光半导体材料有限公司 | 一种化合物及有机电致发光器件 |
| CN112079824A (zh) * | 2019-06-12 | 2020-12-15 | 三星Sdi株式会社 | 用于有机光电器件的化合物、有机光电器件及显示器件 |
| CN112225726A (zh) * | 2020-12-14 | 2021-01-15 | 南京高光半导体材料有限公司 | 一种化合物及有机电致发光器件 |
| CN112300177A (zh) * | 2020-12-21 | 2021-02-02 | 南京高光半导体材料有限公司 | 一种有机电致发光化合物及有机电致发光器件 |
| CN113480526A (zh) * | 2021-06-30 | 2021-10-08 | 南京高光半导体材料有限公司 | 一种含有咔唑的化合物及有机电致发光器件 |
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| CN110869364A (zh) * | 2017-07-04 | 2020-03-06 | 株式会社斗山 | 有机化合物及利用其的有机电致发光元件 |
| CN112079824A (zh) * | 2019-06-12 | 2020-12-15 | 三星Sdi株式会社 | 用于有机光电器件的化合物、有机光电器件及显示器件 |
| CN112028883A (zh) * | 2020-09-02 | 2020-12-04 | 南京高光半导体材料有限公司 | 一种化合物及有机电致发光器件 |
| CN112225726A (zh) * | 2020-12-14 | 2021-01-15 | 南京高光半导体材料有限公司 | 一种化合物及有机电致发光器件 |
| CN112300177A (zh) * | 2020-12-21 | 2021-02-02 | 南京高光半导体材料有限公司 | 一种有机电致发光化合物及有机电致发光器件 |
| CN113480526A (zh) * | 2021-06-30 | 2021-10-08 | 南京高光半导体材料有限公司 | 一种含有咔唑的化合物及有机电致发光器件 |
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