CN113980040B - 一种含硼的不对称螺环化合物及其在有机电致发光器件中的应用 - Google Patents
一种含硼的不对称螺环化合物及其在有机电致发光器件中的应用 Download PDFInfo
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- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 229910052796 boron Inorganic materials 0.000 title claims abstract description 18
- 150000003413 spiro compounds Chemical class 0.000 title claims abstract description 16
- 239000000463 material Substances 0.000 claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 229910052711 selenium Inorganic materials 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims description 19
- 238000002347 injection Methods 0.000 claims description 7
- 239000007924 injection Substances 0.000 claims description 7
- 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 claims description 6
- 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 claims description 6
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 13
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- 238000010791 quenching Methods 0.000 abstract description 3
- 239000011669 selenium Substances 0.000 abstract description 3
- 125000001424 substituent group Chemical group 0.000 abstract description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 abstract description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 2
- 239000001301 oxygen Substances 0.000 abstract description 2
- 239000011593 sulfur Substances 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 238000001819 mass spectrum Methods 0.000 description 11
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 11
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- 238000000921 elemental analysis Methods 0.000 description 9
- 229950000688 phenothiazine Drugs 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 description 5
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- GTIWFNAUYPVPAT-UHFFFAOYSA-N 1-bromo-2-chloro-3-fluorobenzene Chemical compound FC1=CC=CC(Br)=C1Cl GTIWFNAUYPVPAT-UHFFFAOYSA-N 0.000 description 3
- ILFYOWGJBKEMSK-UHFFFAOYSA-N 10h-phenoselenazine Chemical group C1=CC=C2NC3=CC=CC=C3[Se]C2=C1 ILFYOWGJBKEMSK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
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- 238000011161 development Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000007738 vacuum evaporation Methods 0.000 description 2
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
- WRJXIIFHUQBLSW-UHFFFAOYSA-N 1,5-dibromo-2-chloro-3-fluorobenzene Chemical compound FC1=CC(Br)=CC(Br)=C1Cl WRJXIIFHUQBLSW-UHFFFAOYSA-N 0.000 description 1
- NYLNBNAPLADVTL-UHFFFAOYSA-N 1-bromo-2-chloro-3,5-difluorobenzene Chemical compound FC1=CC(F)=C(Cl)C(Br)=C1 NYLNBNAPLADVTL-UHFFFAOYSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- OYFFSPILVQLRQA-UHFFFAOYSA-N 3,6-ditert-butyl-9h-carbazole Chemical compound C1=C(C(C)(C)C)C=C2C3=CC(C(C)(C)C)=CC=C3NC2=C1 OYFFSPILVQLRQA-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
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- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
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- 230000001052 transient effect Effects 0.000 description 1
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- -1 tri-tert-butylphosphine tetrafluoroborate Chemical compound 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
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Abstract
一种含硼的不对称螺环化合物及其在有机电致发光器件中的应用，属于有机电致发光器件技术领域。本发明所述的含硼的不对称螺环化合物作为发光层掺杂客体材料使用，其是在高效率的含咔唑骨架三配位硼发光化合物引入氧、硫、硒等杂原子，利用重原子效应促进自旋轨道耦合来提高三重态到单线态激子的反向系间窜越速率，减弱三线态激子湮灭过程。此外，引入大体积的外围取代基来抑制分子之间的相互作用，在一定程度上可以缓解分子与分子之间的相互淬灭过程。由此制备的有机电致发光器件克服了多重共振材料在高亮度下效率衰减严重等缺点，实现了具有高效率、高色纯度和低效率滚降的有机电致发光器件，对有机电致发光技术进一步普及有重要推动作用。
Description
技术领域
本发明属于有机电致发光器件技术领域，具体涉及一种含硼的不对称螺环化合物及其在有机电致发光器件中的应用。
背景技术
有机电致发光二极管(Organic Light Emission Diodes,OLED)是一种新型的显示技术，具有亮度高、响应快、视角宽、工艺简单、可柔性化等优点，在全彩色显示和照明应用技术中取得了较大的进展，成为当前产业化的热点趋势。近年来，第三代发光材料-热活化延迟荧光(Thermally-Activated Delayed Fluorescence，TADF)材料由于可以有效利用三重态激子被广泛开发并应用于电子器件中，已成为发光材料领域的前沿研究热点。然而当前的TADF材料大部分均采用给-受体型结构，基态和激发态之间的振动耦合和激发态结构弛豫作用，导致其激发光谱的半峰宽(full-width at half maximum,FWHM>70nm)较宽，无法满足全彩显示技术高色纯度的技术需求。尽管采用滤光片或者光学微腔的器件结构可以满足显示对于色纯度的要求，但是这样不仅仅使得器件结构复杂，同时导致很大的能量损失，不利于节能环保的要求。
近年来，虽然具有多重共振效应(multiple resonance,MR)的新型TADF材料被报道可以实现高色纯度和高发光效率。但是其较大的HOMO(Lowest Unoccupied MolecularOrbital：已占有电子的能级最高的轨道)和LUMO(Highest Occupied Molecular Orbital：未占有电子的能级最低的轨道称为最低未占轨道)重叠，会导致材料的单、三线态能极差(△EST)较大，三线态到单线态激发态的反向系间窜越速率(reverse intersystemcrossing rate,kRISC)很慢，这都会导致三线态的寿命很长。在器件实际工作过程中，随着电流密度增加，生成的三线态激子来不及迅速反向系间窜越到单线态激发态，造成器件中三线态激子的大量累积，从而会被各种非辐射相互作用湮灭，导致高亮度下严重的效率滚降，不利于材料的实际应用。另外，该硼/氮多重共振体系化合物具有较大的刚性平面结构，分子与分子之间的相互作用很强，容易聚集，在制备电致发光器件时容易产生聚集诱导淬灭效应，从而进一步导致材料的发光性能和器件的色纯度变差。
因此，开发效率高、色纯度高、而且在高亮度下能保持高效率的新型有机发光材料意义重大，对OLEDs技术进一步普及有重要推动作用。
发明内容
本发明所要解决的技术问题是现有MR-TADF材料体系中kRISC较慢，三线态激子湮灭和分子之间的聚集诱导淬灭效应严重，导致电致发光器件在高亮度下效率滚降严重。针对现有问题，本发明提供了一种新型含硼的不对称螺环化合物，在高效率的含咔唑骨架三配位硼发光化合物引入氧、硫、硒等杂原子，利用重原子效应促进自旋轨道耦合来提高三重态到单线态激子的反向系间窜越速率。此外，引入大体积的外围取代基来抑制分子之间的相互作用，有利于在高亮度下实现高的效率，克服了MR-TADF材料高亮度下器件效率衰减严重等缺点。
本发明所述的一种新型高效含硼的不对称螺环化合物，其结构式如下所示：
其中R1为O、S或Se，
R2为
进一步，本发明所述的一种新型高效含硼的不对称螺环化合物，其结构式如下之一所示：
采用本发明产物制备的有机电致发光器件由阴极、阳极和两电极之间的一层或多层有机层构成，有机层中至少一层为发光层，且所述发光层由本发明制备的含硼的不对称螺环化合物作为掺杂客体材料、PhCzBCz作为掺杂主体材料构成，客体材料的质量掺杂比例为2～5％。该电致发光器件可以用于制备有机电致发光显示器或有机电致发光照明光源。
进一步，本发明的实施方案提供了一种有机电致发光器件，由下至上依次为透明基底、ITO导电薄膜(阳极)、空穴注入层(HATCN)、空穴传输层(TAPC)、激子阻挡层(TCTA和mCP)、发光层、电子传输层(TmPyPB)、电子注入层(LiF)和阴极层(Al)，所有功能层均可采用真空蒸镀成膜工艺制备而成。
作为优选，该器件中所用到的一些有机化合物均为市售或者按照已知文献或专利进行制备，分子结构式如下所示：
本发明的有益效果为：
本发明的不对称螺环化合物同时具有高的发光效率以及高的反向系间窜越速率。在中心苯环的一侧引入刚性的咔唑基团，增大了分子的刚性，有利于进一步减少其振动弛豫，从而确保使目标MR-TADF分子保持高辐射跃迁速率；同时在苯环的另一侧引入含有杂原子(O、S、Se)的吩噁嗪或吩噻嗪衍生物给体，利用重原子效应促进自旋轨道耦合来提高三重态到单线态激子的反向系间窜越速率，减弱三线态激子湮灭过程。此外，引入大体积的外围取代基来抑制分子之间的相互作用，在一定程度上可以缓解分子与分子之间的相互淬灭过程。由此制备的有机电致发光器件克服了MR-TADF材料在高亮度下效率衰减严重等缺点，实现了具有高效率、高色纯度和低效率滚降的有机电致发光器件，对有机电致发光技术进一步普及有重要推动作用。
附图说明
图1：本发明所制备的有机电致发光器件的结构示意图，图中，1为透明基底，2为ITO阳极、3为空穴注入层、4为空穴传输层、5为激子阻挡层、6为有机发光层、7为电子传输层、8为电子注入层、9为阴极。
图2：化合物BN-4的单/三线态能级和自旋轨道图及理论计算得到的耦合常数；理论计算表明BN-4具有高的自旋轨道耦合常数，有利于三线态到单线态的反向系间窜越。
图3：化合物BN-4的紫外、荧光和低温磷光光谱图；发射主峰位于505nm，为纯绿光的发射；通过荧光和低温磷光起峰位计算得到S1和T1的能量分别为2.59eV和2.50eV，计算可得两分子的ΔEST为0.09eV。
图4：化合物BN-4的时间分辨光谱图；包含瞬时(5.0ns)和延迟(17.6μs)两个组分。
图5：化合物BN-4制备的电致发光器件的外量子效率曲线，最大的外量子效率为32.8％；插图为6V驱动电压下的电致发光光谱，电致发光主峰位于516nm，具有很高的色纯度，半峰宽为56nm。
图6：化合物BN-4制备的电致发光器件在不同电压下的电致发光光谱；不同电压下的光谱非常稳定，表明光色的稳定性。
图7：化合物BN-4制备的电致发光器件的电流密度-电压-亮度曲线；器件的最大亮度为26887cd/m2，开启电压为3.3V。
图8：化合物BN-4制备的电致发光器件的电流效率-亮度-功率效率曲线；器件的最大电流效率为108.5cd/A，最大的功率效率为92.1lm/W。
具体实施方式
下面结合附图对本发明作进一步描述，以便于所属技术领域的人员对本实用新型的理解。显然，所描述的实施例仅仅是本实验的一部分，并不是全部的实施例，所属领域的技术熟练人员，根据上述发明内容对本发明做出的非本质性修改、等同替换和改进等，均应包含在本发明的保护范围之内。下述所提及的原料均为市售或者按照已知文献或专利进行制备，未提及的工艺步骤和制备方法均为本领域技术人员所熟知的工艺步骤和制备方法。
实施例1：本实施例BN-1的制备，其步骤如下：
M1的合成：将100mL含有5.58g 3,6-二叔丁基咔唑(20.0mmol)的无水DMF(N,N-二甲基甲酰胺)溶液缓慢滴加到50mL含有13.0g碳酸铯(40.0mmol)的无水DMF溶液中，在室温下搅拌2小时后向其中滴加20mL含有6.27g的1-溴-2-氯-3-氟苯(30.0mmol)的无水DMF溶液，反应体系在150℃下搅拌24小时。然后冷却至室温，倒入1L冰水中，抽滤出白色固体，在真空中干燥，用柱层析分离提纯，展开剂为石油醚：二氯甲烷(体积比10：1)，得到白色固体(7.19g，产率：77％)。质谱MALDI-TOF(m/z)[M+]：测量值为468.34，理论值为468.86。
M2的合成：250mL圆底烧瓶中，将吩噻嗪(2.00g，10.0mmol)，M1(5.62g，12.0mmol)，三(二亚苄基丙酮)二钯(277mg，0.30mmol)，四氟硼酸三叔丁基膦(147mg，0.50mmol)，叔丁醇钠(1.92g，20mmol)溶于100mL甲苯溶液，氮气保护下110℃回流24小时。用二氯甲烷萃取分液，浓缩得到粗产品，柱层析分离提纯，展开剂为石油醚：二氯甲烷(体积比10：1)，得到白色固体(4.12g，产率：70％)。质谱MALDI-TOF(m/z)[M+]：测量值为587.10，理论值为587.22。
BN-1的合成：在氮气氛围保护下，将13.8mL叔丁基锂的正己烷溶液(18.0mmol)缓慢加入到含5.28g的M2(9.0mmol)的100mL叔丁基苯溶液中(0℃)。缓慢升温到60℃，搅拌2小时后，真空除去正己烷，然后冷却到-40℃，加入1.7mL三溴化硼(18.0mmol)，将反应混合物在室温下搅拌0.5小时。接着在0℃下加入3.1mL N,N-二异丙基乙胺(18.0mmol)，然后将反应混合物升至120℃下继续搅拌5小时后，冷却至室温。向反应混合物中加入5mL甲醇以淬灭残留的三溴化硼。将反应体系真空浓缩，柱层析分离提纯，展开剂为石油醚：二氯甲烷(体积比10：1)，得到黄色固体(1.10g，产率：22％)。质谱MALDI-TOF(m/z)[M+]：测量值为560.17，理论值为560.57。元素分析结果：实验值(％)：C，81.39；H，5.94；B，1.95；N，4.98；S，5.71；理论值(％)：C，81.42；H，5.93；B，1.93；N，5.00；S，5.72。
实施例2：本实施例BN-2的制备，其步骤如下：
本实施例与实施例1基本相同，其不同之处在于：本例中需将吩噻嗪换为等物质的量的吩噁嗪，得到淡黄色粉末状固体(1.22g，产率：25％)。质谱MALDI-TOF(m/z)[M+]：测量值为544.32，理论值为544.51。元素分析结果：实验值(％)：C，83.79；H，6.12；B，2.00；N，5.13；O，2.96；理论值(％)：C，83.82；H，6.11；B，1.99；N，5.14；O，2.94。
实施例3：本实施例BN-3的制备，其步骤如下：
本实施例与实施例1基本相同，其不同之处在于：本例中需将吩噻嗪换为等物质的量的吩硒嗪，得到淡黄色粉末状固体(1.01g，产率：18％)。质谱MALDI-TOF(m/z)[M+]：测量值为607.81，理论值为607.47。元素分析结果：实验值(％)：C，75.11；H，5.47；B，1.79；N，4.62；Se，13.01；理论值(％)：C，75.13；H，5.48；B，1.78；N，4.61；Se，13.00。
实施例4：本实施例BN-4的制备，其步骤如下：
本实施例与实施例1基本相同，其不同之处在于：本例中需将1-溴-2-氯-3-氟苯换为等物质的量的1-溴-2-氯-3,5-二氟苯，得到淡黄色粉末状固体(1.12g，产率：15％)。质谱MALDI-TOF(m/z)[M+]：测量值为837.62，理论值为837.98。元素分析结果：实验值(％)：C，81.11；H，6.75；B，1.28；N，5.01；S，3.81；理论值(％)：C，81.13；H，6.74；B，1.29；N，5.01；S，3.83。
实施例5：本实施例BN-5的制备，其步骤如下：
本实施例与实施例4基本相同，其不同之处在于：本例中需将吩噻嗪换为等物质的量的吩噁嗪，得到淡黄色粉末状固体(1.31g，产率：18％)。质谱MALDI-TOF(m/z)[M+]：测量值为821.77，理论值为821.92。元素分析结果：实验值(％)：C，84.77；H，6.88；B，1.31；N，5.12；O，1.93；理论值(％)：C，84.76；H，6.87；B，1.32；N，5.11；O，1.95。
实施例6：本实施例BN-6的制备，其步骤如下：
本实施例与实施例4基本相同，其不同之处在于：本例中需将吩噻嗪换为等物质的量的吩硒嗪，得到淡黄色粉末状固体(1.11g，产率：14％)。质谱MALDI-TOF(m/z)[M+]：测量值为884.76，理论值为884.88。元素分析结果：实验值(％)：C，78.75；H，6.32；B，1.24；N，4.74；Se，8.90；理论值(％)：C，78.73；H，6.38；B，1.22；N，4.75；Se，8.92。
实施例7：本实施例BN-7的制备，其步骤如下：
本实施例与实施例1基本相同，其不同之处在于：本例中需将1-溴-2-氯-3-氟苯换为等物质的量的2-氯-3,5-二溴氟苯，得到淡黄色粉末状固体(1.05g，产率：15％)。质谱MALDI-TOF(m/z)[M+]：测量值为757.69，理论值为757.82。元素分析结果：实验值(％)：C，79.21；H，5.33；B，1.44；N，5.53；S，8.48；理论值(％)：C，79.25；H，5.32；B，1.43；N，5.54；S，8.46。
实施例8：本实施例BN-8的制备，其步骤如下：
本实施例与实施例7基本相同，其不同之处在于：本例中需将吩噻嗪换为等物质的量的吩噁嗪，得到淡黄色粉末状固体(1.32g，产率：20％)。质谱MALDI-TOF(m/z)[M+]：测量值为725.60，理论值为725.70。元素分析结果：实验值(％)：C，82.77；H，5.57；B，1.48；N，5.78；O，4.40；理论值(％)：C，82.75；H，5.56；B，1.49；N，5.79；O，4.41。
实施例9：本实施例BN-9的制备，其步骤如下：
本实施例与实施例7基本相同，其不同之处在于：本例中需将吩噻嗪换为等物质的量的吩硒嗪，得到淡黄色粉末状固体(1.15g，产率：15％)。质谱MALDI-TOF(m/z)[M+]：测量值为851.30，理论值为851.62。元素分析结果：实验值(％)：C，70.50；H，4.72；B，1.28；N，4.91；Se，18.57；理论值(％)：C，70.52；H，4.73；B，1.27；N，4.93；Se，18.54。
下通过将本发明的化合物具体应用到有机电致发光器件中测试实际使用性能来展示和验证本发明的技术效果和优点。
效果实施例1：有机电致发光器件BN-1的制备
下面通过将本发明的化合物具体应用到有机电致发光器件中测试实际使用性能来展示和验证本发明的技术效果和优点。具体的器件制备工艺及器件性能测试实验操作如下：器件的制备过程如下：基片铟锡氧化物(ITO)导电玻璃的准备：基片依次用去离子水、异丙醇、丙酮、甲苯、丙酮、异丙醇在超声浴中各自清洗20分钟，并于烘箱中烘干；在紫外臭氧清洗机中对ITO导电玻璃表面处理40分钟后，将其移入真空蒸镀设备中(腔体内压力＜2×10-4Pa)；在阳极ITO导电玻璃上，真空蒸镀空穴注入层HATCN，厚度为6nm；在HATCN上，真空蒸镀空穴传输层TAPC，厚度为30nm：在TAPC上，蒸镀激子阻挡层TCTA，厚度为5nm；在TCTA上，蒸镀激子阻挡层mCP，厚度为5nm；在mCP之上，蒸镀发光层，厚度为20nm；在发光层之上，蒸镀电子传输层TmPyPB，厚度为40nm；在TPBi之上，蒸镀电子传输层LiF，厚度为1nm；在LiF之上，蒸镀阴极Al，厚度为100nm。
所述有机电致发光器件BN-1的结构如下：ITO/HATCN(6nm)/TAPC(30nm)/TCTA(5nm)/mCP(5nm)/EML(20nm)/TmPyPB(40nm)/LiF(1nm)/Al(100nm)，EML代表发光层，发光层由质量百分含量97％的主体材料PhCzBCz和质量百分含量3％的客体发光材料BN-1组成。
针对本实施例制备得到的有机电致发光器件BN-1施加直流电压，使用Spectrascan PR655亮度计来评价发光性能，使用电脑控制的Keithley 2400数字源表测量电流-电压特性。作为发光特性，测定在随外加直流电压变化下的电致光谱、半峰宽、CIE色坐标值、外量子效率(％)、功率效率(lm/W)、最大亮度(cd/m2)。器件的详细电致发光性能数据列于表1中。所制作的器件的测定值为光谱峰值为520nm，半峰宽为54nm，CIE色坐标值为(0.26，0.65)，最大功率效率为86.1lm/W和最大的亮度为29793cd/m2，最大外量子效率为27.6％。在亮度达到100cd/m2和1000cd/m2时，外量子效率仍然能保持在26.2％和17.3％。
效果实施例2：有机电致发光器件BN-4的制备
与效果实施例1的制备方法相同，区别在于，将发光层中采用的客体发光材料BN-1替换为BN-4，具体器件结构如下：ITO/HATCN(6nm)/TAPC(30nm)/TCTA(5nm)/mCP(5nm)/EML(20nm)/TmPyPB(40nm)/LiF(1nm)/Al(100nm)，EML代表发光层，发光层由质量百分含量97％的主体材料PhCzBCz和质量百分含量3％的客体发光材料BN-4组成。
针对本实施例制备得到的有机电致发光器件BN-4测定器件性能结果如下：本实施例的有机电致发光器件的外量子效率曲线和6V驱动电压下的电致发光光谱、不同电压下的电致发光光谱、电流密度-电压-亮度曲线、电流效率-亮度-功率效率曲线分别如图5、图6、图7和图8所示。器件的详细电致发光性能数据列于表1中。所制作的器件的测定值为光谱峰值为516nm，半峰宽为56nm，CIE色坐标值为(0.24，0.63)，最大功率效率为92.1lm/W和最大的亮度为26887cd/m2，最大外量子效率为32.8％。在亮度达到100cd/m2和1000cd/m2时，外量子效率仍然能保持在30.8％和23.5％。
表1：效果实施例所提供的电致发光器件数据参数
以上所述仅为本发明的较佳实施例，并不用以限制本发明，凡在本发明的精神和原则之内，所作的任何修改、等同替换、改进等，均应包含在本发明的保护范围之内。
Claims (5)
1.一种含硼的不对称螺环化合物，其结构式如下所示：
其中R1为O、S或Se；
R2为H、中的一种。
2.如权利要求1所述的一种含硼的不对称螺环化合物，其结构式如下之一所示：
3.权利要求1或2所述的一种含硼的不对称螺环化合物在制备有机电致发光器件中的应用。
4.如权利要求3所述一种含硼的不对称螺环化合物在制备有机电致发光器件中的应用，其特征在于：该有机电致发光器件由下至上，依次为透明基底、ITO导电薄膜阳极、空穴注入层HATCN、空穴传输层TAPC、激子阻挡层TCTA和mCP、发光层、电子传输层TmPyPb、电子注入层LiF和阴极层Al；发光层由权利要求1或2制备的含硼的不对称螺环化合物作为掺杂客体材料、PhCzBCz作为掺杂主体材料构成，客体材料的质量掺杂比例为2～5％；ITO为铟锡氧化物，上述各化合物的结构式如下所示，
5.如权利要求4所述一种含硼的不对称螺环化合物在制备有机电致发光器件中的应用，其特征在于：该电致发光器件用于制备有机电致发光显示器或有机电致发光照明光源。
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