CN111362954A - 一种以含烯键七元环的结构为核心的化合物及其应用 - Google Patents
一种以含烯键七元环的结构为核心的化合物及其应用 Download PDFInfo
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- CN111362954A CN111362954A CN201811591811.8A CN201811591811A CN111362954A CN 111362954 A CN111362954 A CN 111362954A CN 201811591811 A CN201811591811 A CN 201811591811A CN 111362954 A CN111362954 A CN 111362954A
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- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07—ORGANIC CHEMISTRY
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
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- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
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- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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Abstract
本发明公开了一种以含烯键七元环的结构为核心的化合物及其制备方法与应用，所述化合物结构以含烯键七元环为核心，连接给电子基团，具有高的三线态能级(T1)，作为OLED发光器件的电子阻挡层材料使用可有效阻挡发光层的激子能量传递至空穴传输层中，提高激子在发光层中的复合效率，提高能量利用率，从而提高器件发光效率；另外本发明化合物具有较高的玻璃化转变温度和分子热稳定性、合适的HOMO和LUMO能级和较高的Eg，通过器件结构优化，可有效提升OLED器件的光电性能以及OLED器件的寿命。
Description
技术领域
本发明涉及半导体材料技术领域，尤其是涉及一种以含烯键七元环的结构为核心的化合物及其制备方法与在有机电致发光器件上的应用。
背景技术
有机电致发光(OLED:Organic ight Emission Diodes)器件技术既可以用来制造新型显示产品，也可以用于制作新型照明产品，有望替代现有的液晶显示和荧光灯照明，应用前景十分广泛。OLED发光器件犹如三明治的结构，包括电极材料膜层以及夹在不同电极膜层之间的有机功能材料，各种不同功能材料根据用途相互叠加在一起共同组成OLED发光器件。OLED发光器件作为电流器件，当对其两端电极施加电压，并通过电场作用有机层功能材料膜层中的正负电荷时，正负电荷进一步在发光层中复合，即产生OLED电致发光。
当前，OLED显示技术已经在智能手机，平板电脑等领域获得应用，进一步还将向电视等大尺寸应用领域扩展，但是，和实际的产品应用要求相比，OLED器件的发光效率和使用寿命等性能还需要进一步提升。目前对OLED发光器件提高性能的研究包括：降低器件的驱动电压、提高器件的发光效率、提高器件的使用寿命等。为了实现OLED器件的性能的不断提升，不但需要从OLED器件结构和制作工艺的创新，更需要OLED光电功能材料不断研究和创新，创制出更高性能的OLED功能材料。
应用于OLED器件的OLED光电功能材料从用途上可划分为两大类，分别为电荷注入传输材料和发光材料。进一步，还可将电荷注入传输材料分为电子注入传输材料、电子阻挡材料、空穴注入传输材料和空穴阻挡材料，还可以将发光材料分为主体发光材料和掺杂材料。
为了制作高性能的OLED发光器件，要求各种有机功能材料具备良好的光电性能，譬如，作为电荷传输材料，要求具有良好的载流子迁移率，高玻璃化转化温度等，作为发光层的主体材料具有良好双极性，适当的HOMO/LUMO能阶等。
构成OLED器件的OLED光电功能材料膜层至少包括两层以上结构，产业上应用的OLED器件结构则包括空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层等多种膜层，也就是说应用于OLED器件的光电功能材料至少包括空穴注入材料、空穴传输材料、发光材料、电子传输材料等，材料类型和搭配形式具有丰富性和多样性的特点。另外，对于不同结构的OLED器件搭配而言，所使用的光电功能材料具有较强的选择性，相同的材料在不同结构器件中的性能表现也可能完全迥异。
因此，针对当前OLED器件的产业应用要求以及OLED器件的不同功能膜层，器件的光电特性需求，必须选择更适合、性能更高的OLED功能材料或材料组合，才能实现器件的高效率、长寿命和低电压的综合特性。就当前的OLED显示照明产业的实际需求而言，目前OLED材料的发展还远远不够，落后于面板制造企业的要求，作为材料企业开发更高性能的有机功能材料显得尤为重要。
发明内容
针对现有技术存在的上述问题，本发明申请人提供了一种以含烯键七元环的结构为核心的化合物及其在有机电致发光器件上的应用。本发明化合物含有烯键芴及五元环并环结构，具有较高的玻璃化转变温度和分子热稳定性，合适的HOMO和LUMO能级，较高Eg，通过器件结构优化，可有效提升OLED器件的光电性能以及OLED器件的寿命。
本发明的技术方案如下：
一种以含烯键七元环的结构为核心的化合物，所述化合物的结构如通式(1)所示：
通式(1)中，虚线表示为两个基团以单键连接或不连接；
a、b、c、d分别独立地表示为0、1或2；
e、f分别独立地表示为0或1；
所述X表示为氮原子或C-H
R1、R2、R3、R4分别独立地表示为氢原子、氰基、卤素、C1-20烷基、取代或未取代的苯基、取代或未取代的萘基、取代或未取代的萘啶基、取代或未取代的联苯基、取代或未取代的吡啶基、通式(2)或通式(3)所示结构，且至少有一个表示为通式(2)或通式(3)所示结构；
通式(2)、通式(3)中，Ar1、Ar2分别独立地表示为单键、取代或未取代的C6-30亚芳基、含有一个或多个杂原子取代或未取代的5-30元亚杂芳基中的一种；
所述R9、R10、R11分别独立地表示为氢原子、氕、氘、氚、氰基、C1-20烷基、取代或未取代的C6-30芳基、含有一个或多个杂原子取代或未取代的5-30元杂芳基，且R9、R10、R11与通式(2)或通式(3)有并环或取代两种连接方式；
X1表示为-O-、-S-、-C(R14)(R15)-或-N(R16)-；
所述R5、R6、R7、R8分别独立地表示为氢原子、氕、氘、氚、氰基、卤素、C1-20烷基、经取代或未取代的C6-30芳基；当虚线表示为两个基团不连接时，R7、R8还可以表示为通式(3)所示结构；
所述R14～R16分别独立地表示为C1-20烷基、取代或未取代的C6-30芳基、含有一个或多个杂原子取代或未取代的5-30元杂芳基；且R14与R15可相互键结成环；
所述可取代基团的取代基任选自氕、氘、氚、氰基、卤素原子、C1-20的烷基、C6-30芳基、含有一个或多个杂原子的5-30元杂芳基中的一种或多种；
所述杂原子任选自氧原子、硫原子或氮原子中的一种或多种。
作为本发明进一步改进，当R9、R10、R11与通式(2)或通式(3)以取代方式连接时，R9、R10、R11分别独立地表示为氢原子、氕、氘、氚、氰基、甲基、乙基、丙基、异丙基、丁基、叔丁基、戊基、己基、取代或未取代的苯基、取代或未取代的萘基、取代或未取代的萘啶基、取代或未取代的联苯基、取代或未取代的吡啶基、取代或未取代的蒽基、取代或未取代的菲基、取代或未取代的苯并菲基、取代或未取代的芘基、通式(5)、通式(7)或通式(8)所示结构；当R9、R10、R11与通式(2)或通式(3)以并环方式连接时，R9、R10、R11分别独立地表示为氢原子、通式(4)或通式(6)所示结构；
所述X2、X3、X4、X5、X6分别独立的表示为单键、-O-、-S-、-C(R17)(R18)-或-N(R19)-；且X3、X5、X6还可以表示为单键；
通式(5)中，R12、R13分别独立的表示为取代或未取代的C6-30芳基、含有一个或多个杂原子取代或未取代的5-30元杂芳基；
所述L表示为取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚吡啶基、取代或未取代的亚联苯基；
所述Z表示为氮原子或C(R20)；且连接位点处的Z表示为碳原子；
所述R17～R19分别独立地表示为C1-20烷基、取代或未取代的C6-30芳基、含有一个或多个杂原子取代或未取代的5-30元杂芳基；且R17与R18还可相互键结成环；
所述R20表示为氢原子、氕、氘、氚、氰基、卤素、C1-20烷基、经取代或未取代的C6-30芳基；
通式(4)、通式(6)中，由*标记的两个相邻位置以并环方式与通式(2)或通式(3)中两个相邻位置L1-L2、L2-L3、L3-L4、L'1-L'2、L'2-L'3、L'3-L'4、L5-L6、L6-L7或L7-L8相连；
所述可取代基团的取代基任选自氕、氘、氚、氰基、卤素原子、C1-20的烷基、C6-30芳基、含有一个或多个杂原子的5-30元杂芳基中的一种或多种；
所述杂原子任选自氧原子、硫原子或氮原子中的一种或多种。
作为本发明进一步改进，所述R9、R10不同时表示为氢原子；所述R11不表示为氢原子。
作为本发明进一步改进，所述Ar1、Ar2分别独立地表示为单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚咔唑基、取代或未取代的亚二苯并呋喃基、取代或未取代的亚苯并噻吩基、取代或未取代的亚萘啶基、取代或未取代的亚吡啶基中的一种；
所述R12、R13分别独立的表示为取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的咔唑基、取代或未取代的苯并呋喃基、取代或未取代的苯并噻吩基、取代或未取代的9，9-二甲基芴基、取代或未取代的9，9-二苯基芴基、取代或未取代的9，9-螺芴基、取代或未取代的吡啶基、取代或未取代的喹啉基、取代或未取代的异喹啉基、取代或未取代的嘧啶基、取代或未取代的菲基、取代或未取代的蒽基中的一种；
所述R14～R19分别独立的表示为甲基、乙基、丙基、异丙基、丁基、叔丁基、戊基、己基、取代或未取代的苯基、取代或未取代联苯基、取代或未取代的萘基、取代或未取代的吡啶基中的一种；
所述R5、R6、R7、R8、R20分别独立地表示为氢原子、氕、氘、氚、氰基、氟原子、甲基、乙基、丙基、异丙基、丁基、叔丁基、戊基、己基、取代或未取代的苯基、取代或未取代联苯基、取代或未取代的萘基、取代或未取代的吡啶基中的一种；
所述可取代集团的取代基任选自氟原子、氰基、苯基、联苯基、萘基、呋喃基、咔唑基、噻吩基或吡啶基中的一种或多种。
所述以含烯键七元环的结构为核心的化合物，优选的具体结构为：
一种有机电致发光器件，包括有机薄膜层，至少一层有机薄膜层含有所述以含烯键七元环的结构为核心的化合物。
进一步优选，所述的有机电致发光器件，包括电子阻挡材料/空穴传输层，其电子阻挡材料/空穴传输层含有所述以含烯键七元环的结构为核心的化合物。
进一步优选，所述的有机电致发光器件，包括发光层，其发光层含有所述以含烯键七元环的结构为核心的化合物。
一种显示元件，所述显示元件含有所述的有机电致发光器件。
本发明有益的技术效果在于：
(1)本发明的化合物以含烯键七元环的结构为核心，连接给电子基团，具有高的三线态能级(T1)，作为OLED发光器件的电子阻挡层材料使用可有效阻挡发光层的激子能量传递至空穴传输层中，提高激子在发光层中的复合效率，提高能量利用率，从而提高器件发光效率。
(2)本发明的化合物使得电子和空穴在发光层的分布更加平衡，在恰当的HOMO能级下，提升了空穴注入和传输性能；在合适的LUMO能级下，又起到了电子阻挡的作用，提升激子在发光层中的复合效率；可有效提高激子利用率和高荧光辐射效率，降低器件电压，提高器件的电流效率和寿命；从而更易于获得器件的高效率。在OLED发光器件中具有良好的应用效果，具有良好的产业化前景。
附图说明
图1为本发明所列举的材料应用于OLED器件的结构示意图；
图中，1为透明基板层、2为ITO阳极层、3为空穴注入层、4、第一空穴传输层、5第二空穴传输层(电子阻挡层)、6为发光层、7为电子传输层、8为电子注入层、9为阴极反射电极层。
图2为本发明化合物制备的OLED器件的电流效率随温度变化的曲线。
具体实施方式
下面结合附图和实施例，对本发明进行具体描述。
下述实施例中所有原料均采购于中节能万润股份有限公司。
实施例1：中间体M的制备：
将原料B-1(0.5mmol)溶解在四氢呋喃(1.5ml)中并将溶液冷却至-78℃(干冰/丙酮)。然后，用少量三甲基硅重氮甲烷(2M，0.25ml，0.5mmol)的醚溶液处理混合物，直至原料C-1的强烈颜色消失；使混合物缓慢升温至-45℃，直到观察到N2的消除。然后加入原料A-1(0.5mmol)使用冰浴(0℃)放置10分钟，向溶液中加入四丁基氟化铵(1M的四氢呋喃溶液，1ml，1mmol)的混合物溶液。在真空下除去溶剂后，通过柱色谱法纯化粗产物得到中间体M-1。元素分析结构(分子式C28H17Br)：理论值C,77.61；H,3.95；Br,18.44；测试值：C,77.62；H,3.95；Br,18.43。ESI-MS(m/z)(M+)：理论值为432.05，实测值为432.51。
以中间体M-1的合成方法制备中间体M，具体结构如表1所示。
表1
实施例2：化合物3的制备：
将0.01mol中间体M-1和0.012mol原料C-1溶解于甲苯和乙醇的150mL(V甲苯:V乙醇＝5:1)混合溶液中，除氧后加入0.0002mol Pd(PPh3)4和0.02mol K2CO3，在通入氮气的气氛下110℃反应24个小时，取样点板，待原料反应完全后，冷却、过滤，将滤液旋蒸除去溶剂，粗产品过硅胶柱，得到化合物3；元素分析结构(分子式C52H31NO)：理论值C,91.07；H,4.56；N,2.04；测试值：C,91.07；H,4.56；N,2.05。ESI-MS(m/z)(M+)：理论值为685.24，实测值为685.80。
实施例3：化合物12的制备：
化合物12的制备方法同实施例2，不同之处在于用中间体M-2替换中间体M-1，用原料C-2替换原料C-1；元素分析结构(分子式C52H31NO)：理论值C,91.07；H,4.56；N,2.04；测试值：C,91.06；H,4.56；N,2.04。ESI-MS(m/z)(M+)：理论值为685.24，实测值为685.77。
实施例4：化合物19的制备：
化合物19的制备方法同实施例2，不同之处在于用原料C-3替换原料C-1；元素分析结构(分子式C55H37N)：理论值C,92.79；H,5.24；N,1.97；测试值：C,92.79；H,5.24；N,1.97。ESI-MS(m/z)(M+)：理论值为711.29，实测值为711.47。
实施例5：化合物30的制备：
250ml的三口瓶，在通入氮气的气氛下，加入0.01mol原料D-1，0.012mol的中间体M-2，0.03mol叔丁醇钾，1×10-4molPd2(dba)3，1×10-4mol三苯基膦，150ml甲苯，加热回流12小时，取样点板，反应完全；自然冷却，过滤，滤液旋蒸，过硅胶柱，得到化合物30；元素分析结构(分子式C49H33N)：理论值C,92.57；H,5.23；N,2.20；测试值：C,92.56；H,5.23；N,2.21。ESI-MS(m/z)(M+)：理论值为635.26，实测值为635.66。
实施例6：化合物40的制备：
化合物40的制备方法同实施例2，不同之处在于用中间体M-3替换中间体M-1，原料C-4替换原料C-1；元素分析结构(分子式C58H36N2)：理论值C,91.55；H,4.77；N,3.68；测试值：C,91.56；H,4.77；N,3.67。ESI-MS(m/z)(M+)：理论值为760.29，实测值为760.79。
实施例7：化合物49的制备：
化合物49的制备方法同实施例2，不同之处在于用中间体M-4替换中间体M-1；元素分析结构(分子式C52H33NO)：理论值C,90.80；H,4.84；N,2.04；测试值：C,90.80；H,4.84；N,2.05。ESI-MS(m/z)(M+)：理论值为687.26，实测值为687.88。
实施例8：化合物58的制备：
化合物58的制备方法同实施例2，不同之处在于用中间体M-5替换中间体M-1，原料C-2替换原料C-1；元素分析结构(分子式C52H33NO)：理论值C,90.80；H,4.84；N,2.04；测试值：C,90.80；H,4.84；N,2.05。ESI-MS(m/z)(M+)：理论值为687.26，实测值为687.89。
实施例9：化合物71的制备：
化合物71的制备方法同实施例2，不同之处在于用中间体M-6替换中间体M-1，原料C-3替换原料C-1；元素分析结构(分子式C55H39N)：理论值C,92.53；H,5.51；N,1.96；测试值：C,92.52；H,5.51；N,1.97。ESI-MS(m/z)(M+)：理论值为713.31，实测值为713.88。
实施例10：化合物77的制备：
化合物77的制备方法同实施例2，不同之处在于用中间体M-4替换中间体M-1，原料C-5替换原料C-1；元素分析结构(分子式C58H35NO4)：理论值C,86.01；H,4.36；N,1.73；测试值：C,86.01；H,4.36；N,1.74。ESI-MS(m/z)(M+)：理论值为809.26，实测值为809.67。
实施例11：化合物90的制备：
化合物90的制备方法同实施例2，不同之处在于用中间体M-5替换中间体M-1，原料C-6替换原料C-1；元素分析结构(分子式C58H38N2)：理论值C,91.31；H,5.02；N,3.67；测试值：C,91.32；H,5.02；N,3.66。ESI-MS(m/z)(M+)：理论值为762.30，实测值为762.66。
实施例12：化合物101的制备：
化合物101的制备方法同实施例2，不同之处在于用中间体M-6替换中间体M-1，原料C-7替换原料C-1；元素分析结构(分子式C58H40N2)：理论值C,91.07；H,5.27；N,3.66；测试值：C,91.06；H,5.27；N,3.67。ESI-MS(m/z)(M+)：理论值为764.32，实测值为764.74。
实施例13：化合物112的制备：
化合物112的制备方法同实施例2，不同之处在于用中间体M-3替换中间体M-1，原料C-8替换原料C-1；元素分析结构(分子式C54H33N)：理论值C,93.21；H,4.78；N,2.01；测试值：C,93.22；H,4.78；N,2.00。ESI-MS(m/z)(M+)：理论值为695.26，实测值为695.96。
实施例14：化合物127的制备：
化合物127的制备方法同实施例2，不同之处在于用中间体M-7替换中间体M-1，原料C-9替换原料C-1；元素分析结构(分子式C52H31NO)：理论值C,91.07；H,4.56；N,2.04；测试值：C,91.07；H,4.56；N,2.05。ESI-MS(m/z)(M+)：理论值为685.24，实测值为685.74。
实施例15：化合物138的制备：
化合物138的制备方法同实施例2，不同之处在于用原料C-10替换原料C-1；元素分析结构(分子式C64H37NO2)：理论值C,90.22；H,4.38；N,1.64；测试值：C,90.21；H,4.38；N,1.64。ESI-MS(m/z)(M+)：理论值为851.28，实测值为851.28。
实施例16：化合物149的制备：
化合物149的制备方法同实施例2，不同之处在于用中间体M-8替换中间体M-1，原料C-11替换原料C-1；元素分析结构(分子式C61H43N)：理论值C,92.74；H,5.49；N,1.77；测试值：C,92.73；H,5.49；N,1.78。ESI-MS(m/z)(M+)：理论值为789.34，实测值为789.78。
实施例17：化合物159的制备：
化合物159的制备方法同实施例2，不同之处在于用中间体M-8替换中间体M-1，原料C-12替换原料C-1；元素分析结构(分子式C50H33N)：理论值C,92.70；H,5.13；N,2.16；测试值：C,92.71；H,5.13；N,2.16。ESI-MS(m/z)(M+)：理论值为647.26，实测值为647.89。
实施例18：化合物168的制备：
化合物168的制备方法同实施例2，不同之处在于用中间体M-8替换中间体M-1，原料C-13替换原料C-1；元素分析结构(分子式C70H46N2O)：理论值C,90.29；H,4.98；N,3.01；测试值：C,90.29；H,4.98；N,3.02。ESI-MS(m/z)(M+)：理论值为930.36，实测值为930.99。
本发明的有机化合物在发光器件中使用，可以作为空穴传输层材料使用。对本发明化合物3、12、19、30、40、49、58、71、77、90、101、112、127、138、149、159、168和182分别进行T1能级、热性能、HOMO能级的测试，检测结果如表2所示。
表2
| 化合物 | T1(ev) | Tg(℃) | Td(℃) | HOMO能级(ev) |
| 化合物3 | 2.75 | 144 | 410 | -5.81 |
| 化合物12 | 2.76 | 143 | 403 | -5.80 |
| 化合物19 | 2.73 | 141 | 410 | -5.81 |
| 化合物30 | 2.75 | 142 | 408 | -5.82 |
| 化合物40 | 2.75 | 142 | 402 | -5.84 |
| 化合物49 | 2.75 | 146 | 404 | -5.83 |
| 化合物58 | 2.77 | 142 | 410 | -5.85 |
| 化合物71 | 2.76 | 144 | 405 | -5.86 |
| 化合物77 | 2.76 | 145 | 409 | -5.83 |
| 化合物90 | 2.75 | 144 | 406 | -5.81 |
| 化合物101 | 2.75 | 145 | 405 | -5.86 |
| 化合物112 | 2.74 | 141 | 411 | -5.83 |
| 化合物127 | 2.75 | 141 | 413 | -5.81 |
| 化合物138 | 2.75 | 142 | 410 | -5.86 |
| 化合物149 | 2.74 | 140 | 410 | -5.83 |
| 化合物159 | 2.75 | 144 | 414 | -5.81 |
| 化合物168 | 2.75 | 150 | 420 | -5.81 |
| 化合物174 | 2.74 | 141 | 408 | -5.80 |
| 化合物182 | 2.74 | 154 | 430 | -5.82 |
注：三线态能级T1是由日立的F4600荧光光谱仪测试，材料的测试条件为2*10-5的甲苯溶液；玻璃化温度Tg由示差扫描量热法(DSC，德国耐驰公司DSC204F1示差扫描量热仪)测定，升温速率10℃/min；热失重温度Td是在氮气气氛中失重1％的温度，在日本岛津公司的TGA-50H热重分析仪上进行测定，氮气流量为20mL/min；最高占据分子轨道HOMO能级是由电离能量测试系统(IPS3)测试，测试为大气环境。
由上表2数据可知，本发明的有机化合物具有较为合适的HOMO能级，可应用于空穴传输层，本发明以氮杂螺芴为核心的有机化合物具有较高的三线态能级及较高的热稳定性，使得所制作的含有本发明有机化合物的OLED器件效率和寿命均得到提升。
以下将通过器件实施例1-20和器件比较例1详细说明本发明的化合物在OLED器件中的应用效果。器件实施例2-20、器件比较例1与器件实施例1相比，制作工艺完全相同，并且所采用了相同的基板材料和电极材料，电极材料的膜厚也保持一致，所不同的是器件中空穴传输层材料或发光层发生了改变。各器件叠层结构如表3所示，各器件的性能测试结果如表4和表5所示。
器件实施例1
如图1所示，一种电致发光器件的制备方法，包括如下步骤：
a)清洗透明基板层1上的ITO阳极层2，分别用去离子水、丙酮、乙醇超声清洗各15分钟，然后在等离子体清洗器中处理2分钟；
b)在ITO阳极层2上，通过真空蒸镀方式蒸镀空穴注入层材料HAT-CN，厚度为10nm，这层作为空穴注入层3；
c)在空穴注入层3上，通过真空蒸镀方式蒸镀空穴传输材料HT-1，厚度为60nm，该层为第一空穴传输层4；
d)在第一空穴传输层4上，通过真空蒸镀方式蒸镀第二空穴传输层(电子阻挡层)材料本发明实施例制备的化合物3，厚度为20nm，该层为第二空穴传输层5；
e)在第二空穴传输层(电子阻挡层)5之上蒸镀发光层6，主体材料为GH-1和GH-2，掺杂材料为GD-1，GH-1、GH-2和GD-1的质量比为45:45:10，厚度为40nm；
f)在发光层6之上，通过真空蒸镀方式蒸镀电子传输材料ET-1和Liq按质量比1:1，厚度为35nm，这层有机材料作为电子传输层7使用；
g)在电子传输层7之上，真空蒸镀电子注入层LiF，厚度为1nm，该层为电子注入层8；
h)在电子注入层8之上，真空蒸镀阴极Al(100nm)，该层为阴极反射电极层9；
按照上述步骤完成电致发光器件的制作后，测量器件的IVL数据和光衰寿命，其结果见表3所示。相关材料的分子结构式如下所示：
表3
各器件实施例与器件比较例1的电流效率和寿命数据见表4所示。
表4
注：LT97指的是在电流密度为10mA/cm2情况下，器件亮度衰减到97％所用时间；
寿命测试系统为韩国脉冲科学M600型OLED器件寿命测试仪。
由表4的器件数据结果可以看出，本发明制备的有机发光器件无论是在效率还是寿命均相对于已知材料的OLED器件获得较大的提升。
进一步的本发明材料制备的OLED器件在低温下工作时效率也比较稳定，将器件实施例3、9、20和器件比较例1在-10～80℃区间进行效率测试，所得结果如表5和图2所示。
表5
从表5和图2的数据可知，器件实施例3、9、20为本发明材料和已知材料搭配的器件结构，与器件比较例1相比，不仅低温效率高，而且在温度升高过程中，效率平稳升高。
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 (9)
1.一种以含烯键七元环的结构为核心的化合物，其特征在于，所述化合物的结构如通式(1)所示：
通式(1)中，虚线表示为两个基团以单键连接或不连接；
a、b、c、d分别独立地表示为0、1或2；
所述X表示为氮原子或C-H；
e、f分别独立地表示为0或1；
R1、R2、R3、R4分别独立地表示为氢原子、氰基、卤素、C1-20烷基、取代或未取代的苯基、取代或未取代的萘基、取代或未取代的萘啶基、取代或未取代的联苯基、取代或未取代的吡啶基、通式(2)或通式(3)所示结构，且至少有一个表示为通式(2)或通式(3)所示结构；
通式(2)、通式(3)中，Ar1、Ar2分别独立地表示为单键、取代或未取代的C6-30亚芳基、含有一个或多个杂原子取代或未取代的5-30元亚杂芳基中的一种；
所述R9、R10、R11分别独立地表示为氢原子、氕、氘、氚、氰基、C1-20烷基、取代或未取代的C6-30芳基、含有一个或多个杂原子取代或未取代的5-30元杂芳基，且R9、R10、R11与通式(2)或通式(3)有并环或取代两种连接方式；
X1表示为-O-、-S-、-C(R14)(R15)-或-N(R16)-；
所述R5、R6、R7、R8分别独立地表示为氢原子、氕、氘、氚、氰基、卤素、C1-20烷基、经取代或未取代的C6-30芳基；当虚线表示为两个基团不连接时，R7、R8还可以表示为通式(3)所示结构；
所述R14～R16分别独立地表示为C1-20烷基、取代或未取代的C6-30芳基、含有一个或多个杂原子取代或未取代的5-30元杂芳基；且R14与R15可相互键结成环；
所述可取代基团的取代基任选自氕、氘、氚、氰基、卤素原子、C1-20的烷基、C6-30芳基、含有一个或多个杂原子的5-30元杂芳基中的一种或多种；
所述杂原子任选自氧原子、硫原子或氮原子中的一种或多种。
2.根据权利要求1所述的化合物，其特征在于，当R9、R10、R11与通式(2)或通式(3)以取代方式连接时，R9、R10、R11分别独立地表示为氢原子、氕、氘、氚、氰基、甲基、乙基、丙基、异丙基、丁基、叔丁基、戊基、己基、取代或未取代的苯基、取代或未取代的萘基、取代或未取代的萘啶基、取代或未取代的联苯基、取代或未取代的吡啶基、取代或未取代的蒽基、取代或未取代的菲基、取代或未取代的苯并菲基、取代或未取代的芘基、通式(5)、通式(7)或通式(8)所示结构；当R9、R10、R11与通式(2)或通式(3)以并环方式连接时，R9、R10、R11分别独立地表示为氢原子、通式(4)或通式(6)所示结构；
所述X2、X3、X4、X5、X6分别独立的表示为单键、-O-、-S-、-C(R17)(R18)-或-N(R19)-；且X3、X5、X6还可以表示为单键；
通式(5)中，R12、R13分别独立的表示为取代或未取代的C6-30芳基、含有一个或多个杂原子取代或未取代的5-30元杂芳基；
所述L表示为取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚吡啶基、取代或未取代的亚联苯基；
所述Z表示为氮原子或C(R20)；且连接位点处的Z表示为碳原子；
所述R17～R19分别独立地表示为C1-20烷基、取代或未取代的C6-30芳基、含有一个或多个杂原子取代或未取代的5-30元杂芳基；且R17与R18还可相互键结成环；
所述R20表示为氢原子、氕、氘、氚、氰基、卤素、C1-20烷基、经取代或未取代的C6-30芳基；
通式(4)、通式(6)中，由*标记的两个相邻位置以并环方式与通式(2)或通式(3)中两个相邻位置L1-L2、L2-L3、L3-L4、L'1-L'2、L'2-L'3、L'3-L'4、L5-L6、L6-L7或L7-L8相连；
所述可取代基团的取代基任选自氕、氘、氚、氰基、卤素原子、C1-20的烷基、C6-30芳基、含有一个或多个杂原子的5-30元杂芳基中的一种或多种；
所述杂原子任选自氧原子、硫原子或氮原子中的一种或多种。
3.根据权利要求1所述的化合物，其特征在于，所述R9、R10不同时表示为氢原子；所述R11不表示为氢原子。
4.根据权利要求1所述的化合物，其特征在于，所述Ar1、Ar2分别独立地表示为单键、取代或未取代的亚苯基、取代或未取代的亚萘基、取代或未取代的亚联苯基、取代或未取代的亚咔唑基、取代或未取代的亚二苯并呋喃基、取代或未取代的亚苯并噻吩基、取代或未取代的亚萘啶基、取代或未取代的亚吡啶基中的一种；
所述R12、R13分别独立的表示为取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的咔唑基、取代或未取代的苯并呋喃基、取代或未取代的苯并噻吩基、取代或未取代的9，9-二甲基芴基、取代或未取代的9，9-二苯基芴基、取代或未取代的9，9-螺芴基、取代或未取代的吡啶基、取代或未取代的喹啉基、取代或未取代的异喹啉基、取代或未取代的嘧啶基、取代或未取代的菲基、取代或未取代的蒽基中的一种；
所述R14～R19分别独立的表示为甲基、乙基、丙基、异丙基、丁基、叔丁基、戊基、己基、取代或未取代的苯基、取代或未取代联苯基、取代或未取代的萘基、取代或未取代的吡啶基中的一种；
所述R5、R6、R7、R8、R20分别独立地表示为氢原子、氕、氘、氚、氰基、氟原子、甲基、乙基、丙基、异丙基、丁基、叔丁基、戊基、己基、取代或未取代的苯基、取代或未取代联苯基、取代或未取代的萘基、取代或未取代的吡啶基中的一种；
所述可取代集团的取代基任选自氟原子、氰基、苯基、联苯基、萘基、呋喃基、咔唑基、噻吩基或吡啶基中的一种或多种。
5.根据权利要求1所述的化合物，其特征在于，所述化合物的具体结构为：
6.一种有机电致发光器件，包括有机薄膜层，其特征在于，至少一层有机薄膜层含有权利要求1～5任一项所述以含烯键七元环的结构为核心的化合物。
7.根据权利6所述的有机电致发光器件，包括电子阻挡材料/空穴传输层，其特征在于，所述电子阻挡材料/空穴传输层含有权利要求1～5任一项所述以含烯键七元环的结构为核心的化合物。
8.根据权利6所述的有机电致发光器件，包括发光层，其特征在于，所述发光层含有权利要求1～5任一项所述以含烯键七元环的结构为核心的化合物。
9.一种显示元件，其特征在于，所述显示元件含有权利要求6～8任一项所述的有机电致发光器件。
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