CN107674087A - 延迟荧光化合物及使用该化合物的有机电致发光装置 - Google Patents
延迟荧光化合物及使用该化合物的有机电致发光装置 Download PDFInfo
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- CN107674087A CN107674087A CN201710797762.2A CN201710797762A CN107674087A CN 107674087 A CN107674087 A CN 107674087A CN 201710797762 A CN201710797762 A CN 201710797762A CN 107674087 A CN107674087 A CN 107674087A
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Abstract
本发明公开了一种延迟荧光化合物及使用该延迟荧光化合物作为发光层及/或电子传输层及/或电洞阻挡层的发光主体的有机电致发光装置,本发明的有机电致发光装置具有良好的性能表现。
Description
技术领域
本发明涉及一种延迟荧光化合物及使用该化合物的有机电致发光(OrganicElectroluminescence,以下简称为有机EL)装置。具体而言,本发明涉及一种具有式(1)通式(2)结构的延迟荧光化合物,且使用该延迟荧光化合物的有机EL装置可显示出极佳的性能。
背景技术
有机电致发光因其高照度、低重量、超薄外型、无背光的自照明、低能耗、广视角、高对比度度、制造简单及反应时间快速而应用在平板显示器中。
有机材料电致发光的首次发现于1950年代早期,由法国南锡大学的安德烈贝诺斯(Andre Bernanose)及其同事所发现。马丁伯普(Martin Pope)及其纽约大学的同事,于1963年在真空下掺有稠四苯葱的单一纯晶体上,首次观察到直流(DC)电致发光。
伊士曼柯达(Eastman Kodak)公司的邓青云(Ching W.Tang)及史蒂芬范斯莱克(Steven Van Slyke)在1987年公布了第一个二极管装置。该装置采用具有单独的电洞传输层和电子传输层的双层结构,可导致操作电压的降低及效率的提高,这促成当今主流的有机EL研究及其装置生产方式。
一般而言,有机EL装置由位于两个电极之间的有机材料层组成,其包括电洞传输层(hole transport layer,HTL)、发光层(emitting layer,EML)、电子传输层(electrontransport layer,ETL)。有机EL的基本机制包括载子的注入、载子传输、复合以及形成发光的激子。当外部电压施加到有机EL装置时,电子及电洞将分别自阴极及阳极注入,电子将从阴极注入最低未占用分子轨域(lowest unoccupied molecular orbital,LUMO)中,且电洞将从阳极注入最高占用分子轨域(highest occupied molecular orbital,HOMO)中。当电子与电洞在发光层中复合时,将会形成激子并随后发光。当发光分子吸收能量以达到激发态时,根据电子及电洞自旋组合方式,而激子可处于单重态或三重态。通过重组电子及电洞形成75%的激子而达到三重激发态。从三重态的衰减为自旋禁阻,因此,荧光电致发光装置仅具有25%的内部量子效率。与荧光电致发光装置相反,磷光有机EL装置利用自旋轨域交互作用来促进单重态及三重态之间的跨系统交叉,从而获得单重态和三重态的发射,以及电致发光装置的内部量子效率从25%到100%。自旋轨域交互作用由一些重原子完成,比如,铱、铑、铂、钯,且可从有机金属复合物的激发金属配位基电荷转移(metal-to-ligandcharge-transfer transition,MLCT)状态来观察磷光跃迁。
近来,安达(Adachi)及同事已开发热活化型延迟荧光(thermally activateddelayed fluorescence,TADF)机制,并将其整合至新型荧光有机EL装置,其通过在单重态及三重态间使用具有较小能量间隙的材料得到的逆向系统间穿越(reverse intersystemcrossing,RISC)机制,将自旋禁阻的三重态激子转化为单重态而获得高效率的激子。然而,于高电流密度中仍需要进一步提高有机EL装置的发光效率。
有机EL利用三重态激子和单重态激子。磷光有机EL通常在发光层(EML)及电子传输层(ETL)之间需要附加电洞阻挡层(hole blocking layer,HBL),或在发光层(EML)及电洞传输层(HTL)之间附加电子阻挡层(electron blocking layer,EBL),因此,与单重态激子相比,三重态激子寿命更长、扩散长度更长。使用HBL或EBL的目的是限制注入的电洞及电子的复合以及使EML内所产生的激子弛豫,藉此可提高装置的效率。为了满足这些作用,电洞阻挡材料或电子阻挡材料必须具有适合于阻断电洞或电子从EML传输至ETL或到HTL的HOMO和LUMO能阶。
对于主动矩阵有机发光二极管(active-matrix organic light-emittingdiode,AMOLED)或有机发光二极管(organic light-emitting diode,OLED)为发光面板的全彩平板显示器来说,于发光层中使用磷光主体材料,对于工业实务使用而言,半衰期、效率及驱动电压方面仍无法令人满意。除此之外,为了呈现有机EL装置的优异性能,磷光发光主体材料需与其他有机薄膜层(例如:电洞阻挡层及电子传输层)配位,以达到低能耗、长半衰期及高效率。因此,需要设计及开发用于有机EL装置的新型材料。
在本发明中,为了使有机EL装置中延迟荧光化合物的偶极材料半衰期延迟、提高效率及显示极佳性能,我们使用一系列的苯并[c][1,2,5]噻二唑(benzo[c][1,2,5]thiadiazole)、苯并[c][1,2,5]二唑(benzo[c][1,2,5]oxadiazole)、苯并[c][1,2,5]硒二唑(benzo[c][1,2,5]selenadiazole)、萘并[2,3-c][1,2,5]噻二唑(naphtho[2,3-c][1,2,5]thiadiazole)、萘并[2,3-c][1,2,5]二唑(naphtho[2,3-c][1,2,5]oxadiazole)及萘并[2,3-c][1,2,5]硒二唑(naphtho[2,3-c][1,2,5]selenadiazole)骨架作为供体并与二氢吲哚咔唑基团(dihydroindolocarbazole group)、二氢茚并咔唑基团(dihydroindenocarbazole group)、啡噻嗪基团(phenothiazine group)、啡嗪基团(phenoxazine group)、二氢吖啶基团(dihydroacridine group)、二氢啡嗪基团(dihydrophenazine group)的供体特征联接,二氢啡嗪基团作为偶极材料,以完成如式(1)或式(2)结构的延迟荧光化合物。现有技术:合成金属161(2011)718–723基于具有咔唑(carbazole)部份的2,1,3-苯并噻二唑(2,1,3-benzothiadiazole)公开了有效的发光材料,WO2015/105137A1亦公开了具有咔唑衍生物作为延迟荧光化合物的苯并噻二唑偶联(benzothiadiazole coupling)。但未有先前技术展示了本发明的用于有机EL装置的延迟荧光化合物。
发明内容
根据上述原因,本发明的目的在于解决现有技术的这些问题,并提供一种发光装置,其在热稳定性、高发光效率及长衰期上表现极佳。本发明公开一种具有式(1)或式(2)结构的有机化合物,其用作发光层的延迟荧光材料及/或发光层及/或电子传输层及/或电洞阻挡层的磷光发光主体,该等层具有良好的电荷载子迁移率,且极佳的使用寿命可降低有机EL装置的驱动电压和能耗、增加有机EL装置的效率并延长其半衰期,具有工业应用的经济优点。
相应地,本发明提供了可用于有机EL装置的延迟荧光化合物。所述延迟荧光化合物的结构由下式(1)或式(2)表示:
其中,D1及D2中的至少一个独立选自由式(3)至式(5)所示的基团:
其中,L1及L2独立选自单键、具有6到30个环碳原子的取代或未取代的亚芳基或具有3到30个环碳原子的取代或未取代的杂亚芳基;X选自氧原子、硫原子及硒原子;p表示0到4的整数;Z为包含选自由O、S、C(R7)(R8)、NR9及Si(R10)(R11)组成的原子或基团的二价桥;Y1至Y6独立选自氮原子或C(Rs),且各个Rs独立选自氢原子、苯基、具有1到30个碳原子的取代或未取代的烷基、具有6到30个碳原子的取代或未取代的芳基;R1至R12独立选自氢原子、卤化物、具有1到30个碳原子的取代或未取代的烷基、具有6到30个碳原子的取代或未取代的芳基、具有6到30个碳原子的取代或未取代的芳烷基及具有3到30个碳原子的一取代或未取代的杂芳基。
附图说明
图1为本发明用于有机电致发光装置的延迟荧光化合物的实施例的有机EL装置示意图;
图2为化合物8的延迟荧光特性的瞬时衰变曲线曲线;
图3为化合物8的UV-Vis(nm)及PL(nm)图表。
[符号说明]
6 透明电极
7 电洞注入层
8 电洞传输层
9 电子阻挡层
10 发光层
11 电洞阻挡层
12 电子传输层
13 电子注入层
14 金属电极
具体实施方法
本发明研究用于有机EL装置的延迟荧光化合物。下面将详细说明其生产、结构及组成部份,以使对本发明的理解更充分。本发明的应用明显不受限于所属技术领域具有通常知识者熟知的具体细节。另一方面,众所周知的一般组成成份和程序不作详细说明,以避免对本发明造成不必要的限制。现在将在下面更详细地介绍本发明的一些优选实施例。然而,应该了解本发明可实际操作于各种其他实施例中,而非本发明详细所述的实施例中,也就是说,本发明还可广泛地应用于其他实施例,且本发明的范围没有明确的限制,除权利要求范围限定的内容。
在本发明的第一个实施例中,提供了可用作有机EL装置的发光层的热活化延迟荧光(thermally activated delayed fluorescence,TADF)材料。所述延迟荧光化合物的结构由下式(1)或式(2)表示:
其中,D1及D2中的至少一个独立选自由式(3)至式(5)所示的基团:
其中,L1及L2独立选自单键、具有6到30个环碳原子的取代或未取代的亚芳基或具有3到30个环碳原子的取代或未取代的杂亚芳基;X选自氧原子、硫原子及硒原子;p表示0到4的整数;Z为包含选自由O、S、C(R7)(R8)、NR9及Si(R10)(R11)组成的原子或基团的二价桥;Y1至Y6独立选自氮原子或C(Rs),且各个Rs独立选自氢原子、苯基、具有1到30个碳原子的取代或未取代的烷基、具有6到30个碳原子的取代或未取代的芳基;R1至R12独立选自氢原子、卤化物、具有1到30个碳原子的取代或未取代的烷基、具有6到30个碳原子的取代或未取代的芳基、具有6到30个碳原子的取代或未取代的芳烷基及具有3到30个碳原子的一取代或未取代的杂芳基。
在本发明的一实施例中,如上述具有式(1)或式(2)结构的延迟荧光化合物,其中L1及L2由下式(6)表示:
其中,Z1及Z5独立选自氮原子或C(Rs),且各个Rs独立选自氢原子、苯基、具有1到30个碳原子的取代或未取代的烷基及具有6到30个碳原子的取代或未取代的芳基。
在本发明的一实施例中,一些延迟荧光化合物的结构如下式所示:
本发明中延迟荧光化合物的详细制备由示例性实施例阐明,但本发明的权利要求范围不限于示例性实施例。实施例1至实施例4展示出了本发明中延迟荧光化合物的制备优选实施例。实施例5展示出有机EL装置及I-V-B的制作、有机EL装置性能测试报告。
实施例1化合物4的合成
4,7-双(12,12-二甲基茚并[2,1-a]咔唑-11(12氢)-基)苯并[c][1,2,5]噻二唑(4,7-bis(12,12-dimethylindeno[2,1-a]carbazol-11(12H)-yl)benzo[c][1,2,5]thiadiazole)的合成
在氮气中将 5g(17.0mmol)4,7-二溴苯并[c][1,2,5]噻二唑(4,7-dibromobenzo[c][1,2,5]thiadiazole)、12.5g(44.2mmol)12,12-二甲基-11,12-二氢茚并[2,1-a]咔唑(12,12-dimethyl-11,12-dihydroindeno[2,1-a]carbazole)、0.3g(0.16mmol)CuI、0.1g(0.51mmol)18-冠-6(18-Crown-6)、9.5g(68.4mmol)K2CO3及25ml NMP混合物回流过夜。反应完成后,使混合物冷却至室温。将溶液倒入水中,随后过滤。固体使用DMF再结晶并通过升华纯化,得到3.6g产物(产率31%)。MS(m/z,FAB+):699.5
实施例2化合物8的合成
4,7-双(12,12-二甲基茚并[2,1-a]咔唑-11(12氢)-基)苯并[c][1,2,5]噻二唑(4,7-bis(12,12-dimethylindeno[2,1-a]carbazol-11(12H)-yl)benzo[c][1,2,5]thiadiazole)的合成
在氮气中将 5g(14.5mmol)4,7-二溴苯并[c][1,2,5]噻二唑(4,7-dibromobenzo[c][1,2,5]thiadiazole)、10.7g(37.8mmol)12,12-二甲基-11,12-二氢茚并[2,1-a]咔唑(12,12-dimethyl-11,12-dihydroindeno[2,1-a]carbazole)、0.3g(0.15mmol)CuI、0.1g(0.44mmol)18-冠-6(18-Crown-6)、8.0g(58.0mmol)K2CO3及25ml NMP混合物回流过夜。反应完成后,使混合物冷却至室温。将溶液倒入水中,随后过滤。固体使用DMF重结晶并通过升华纯化,得到2.9g产物(产率28%)。MS(m/z,FAB+):748.9
实施例3化合物29的合成
4,7-二(10氢-啡噻嗪-10-基)苯并[c][1,2,5]噻二唑(4,7-di(10H-phenothiazin-10-yl)benzo[c][1,2,5]thiadiazole)的合成
将2g(6.8mmol)4,7-二溴苯并[c][1,2,5]噻二唑(4,7-dibromobenzo[c][1,2,5]thiadiazole)、3.4g(17mmol)啡噻嗪(phenothiazine)、1.3g(6.8mmol)碘化铜(I)(Copper(I)iodide)、4.4g(13.6mmol)Cs2CO3、1.25g(4.76mmol)18-冠-6(18-Crown-6)及40ml邻二氯苯(o-Dichlorobenzene)混合物除气并放置在氮气环境中,随后在180℃加热16h。在反应完成后,将混合物热过滤。液体使用二氯甲烷及水萃取,使用无水硫酸镁干燥,移除溶剂并通过硅胶管柱层析法纯化,得到2.5g黄橙色固体产物(产率70%)。
实施例4化合物31的合成
4,7-双(9,9-二甲基吖啶-10(9氢)-基)苯并[c][1,2,5]噻二唑(4,7-bis(9,9-dimethylacridin-10(9H)-yl)benzo[c][1,2,5]thiadiazole)的合成
将2g(6.8mmol)4,7-二溴苯并[c][1,2,5]噻二唑(4,7-dibromobenzo[c][1,2,5]thiadiazole)、3.6g(17mmol)9,9-二甲基-9,10-二氢吖啶(9,9-dimethyl-9,10-dihydroacridine)、1.3g(6.8mmol)碘化铜(I)(Copper(I)iodide)、4.4g(13.6mmol)Cs2CO3、1.25g(4.76mmol)18-冠-6(18-Crown-6)及40ml邻二氯苯(o-Dichlorobenzene)混合物除气并放置在氮气环境中,随后在180℃加热16h。在反应完成后,将混合物热过滤。液体使用二氯甲烷及水萃取,使用无水硫酸镁干燥,移除溶剂并通过硅胶管柱层析法纯化,得到2.2g橙色固体产物(产率58%)。
延迟荧光化合物之光物理特性的测量方法
光物理特征:合成的化合物在高真空下通过温度梯度升华进行纯化,随后在之后的研究中使用。通过在基础压力<10-6torr的真空室中以1-2A/sec的速率于石英基材上热蒸发来制备光物理特征的薄膜。所得薄膜及吸收溶液的吸收光谱由UV-vis-NIR分光亮度仪(UV-1650PC,Shimadzu)检测。光激荧光(Photoluminescence,PL)光谱、冷光量子吸收量(photoluminescence quantum yields,PLQYs)及磷光光谱由荧光分光亮度仪(FluoroMax-P,Horiba Jobin Yvon Inc.)检测薄膜或稀释溶液的PLQYs使用配备校准积分球的该荧光分光亮度仪来检测。使用选定的单色激发光来激发位于校准积分球中的激发样本。通过对比单色激发光及PL发射的光谱强度,测定PL量子吸收量。通过配有微秒闪光灯作为脉冲激发光源的荧光分光亮度仪在77K(液氮温度)下进行薄膜或稀释溶液的磷光光谱。在发射光谱的脉冲激发及收集之间插入10-ms延迟时间。通过使用具有荧光寿命系统的时间相关单光子计数技术(FluoroCube,Horiba Jobin Yvon Inc.)及来自UV发光二极管的奈秒(nanosecond)脉冲光激发(300nm)来监控PL峰值处强度的衰减,以确定时间解析(time-resolved)PL(PL衰减曲线)。将样本放置在具有温度控制的真空低温恒温室中。使用具有发射光谱的脉冲激发及收集之间为200-ns延迟时间及10-ns延迟时间的相同荧光寿命系统来收集瞬时成份及延迟成份的PL光谱。电化学特征:使用CHI619B恒电位仪的循环伏安法来量测氧化/还原电位。通过使用0.1Mn-Bu4NPF6(TBAPF6)在CH2Cl2中作为支持电解质,扫描速率为100mV s-1,用循环伏安法测定氧化电位。通过使用0.1M n-Bu4NClO4(TBAP)在DMF中作为支持电解质,扫描速率为100mV s-1,记录还原电位。使用包含银/氯化银(Ag/AgCl)、铂金线及玻璃碳电极分别作为参考、计数及工作电极的标准3-电极电池。记录所有电位以Ag/AgCl(饱和)作为参考电极时,CH2Cl2/TBAPF6中二茂铁铁/二茂铁离子(Fc/Fc+)氧化还原发生于氧化出现在E’o=+0.47V,且二茂铁/二茂铁离子(Fc/Fc+)氧化还原发生于还原出现在E”o=+0.51V。
图2显示化合物8的延迟荧光特征的甲苯溶液的瞬时衰变曲线,图3显示出了化合物8的光致发光光谱。
生产有机EL装置的一般方法
将阻值为9~12奥姆/平方米且厚度为120~160nm的铟锡氧化物(Indium TinOxide,ITO)涂层玻璃在超声波浴(例如,洗涤剂、等离子水)中进行多次清洗。在气相沉积有机层之前,用紫外光(UV)和臭氧进一步处理清洗后的ITO基底。ITO基底的所有预处理过程在洁净室(100级)内进行。
将有机层通过高真空单位(10-7Torr)的气相沉积法依次施加在ITO基底上,比如:电阻加热石英船。每层的厚度和气相沉积速率(0.1~0.3nm/sec)由石英晶体监视器来精确监控或设置。如上所述,还可以使单层中包含一种以上的化合物,即在一般主体材料中掺杂有掺杂材料。这是通过来自两个或多个来源的共气相法来实现的。
在该有机EL装置中,将二吡嗪[2,3-f:2,3-]喹喔啉-2,3,6,7,10,11-六腈(dipyrazino[2,3-f:2,3-]quinoxaline-2,3,6,7,10,11-hexacarbonitrile)(HAT-CN)用作电洞注入层,且N4,N4’-二二(联苯-4-基)-N4,N4’-二二苯基联苯基-4,4’-二胺(N4,N4’-di(biphenyl-4-yl)-N4,N4’-diphenylbiphenyl-4,4’-diamine)(HT1)用作电洞传输层,N-(联苯-4-基)-9,9-二甲基-N-(4’-苯基联苯-4-基)-9H-茀-2-胺(N-(biphenyl-4-yl)-9,9-dimethyl-N-(4’-phenyl biphenyl-4-yl)-9H-fluoren-2-amine)(EB2)用作电洞阻挡层,化合物H1用作与本实施例对比的磷光主体及延迟荧光主体。这些化合物的化学结构式如下式所示:
本发明中制备的以下延迟荧光化合物优选实施例可通过有机EL装置验证为并用作为延迟荧光掺杂剂、磷光主体、电洞阻挡材料或电子传输材料。使用对比化合物Q(CCQ)作为本实施例中对比化合物的延迟荧光掺杂剂。
有机铱络合物广泛用作发光层的磷光掺杂剂,Ir(ppy)3广泛用作有机EL装置的发光层的磷光绿色掺杂剂。
2,2’,2”-(1,3,5-苯并三嗪)-三(1-苯基-1-H-苯并咪唑)(2,2’,2”-(1,3,5-Benzinetriyl)-tris(1-phenyl-1-H-benzimidazole))(TPBi)及HB3(参见下列化学结构)用作电洞阻挡材料(HBM),且2-(10,10-二甲基-10氢-茚并[2,1-b]三亚苯-12-基)-4,6-二苯基-1,3,5-三嗪(2-(10,10-dimethyl-10H-indeno[2,1-b]triphenylen-12-yl)-4,6-diphenyl-1,3,5-triazine)(ET2)用作电子传输材料,以在有机EL装置中与8-羟基喹啉-锂(8-hydroxyquinolato-lithium,LiQ)共沉积。本实施例中用于作为生产标准有机EL装置对比材料的其他OLED材料的现有化合物的结构如下式所示:
有机EL装置一般包含通过热蒸发形成阴极的低功函数金属,比如,Al、Mg、Ca、Li及K,且该低功函数金属可有助于电子从阴极注入电子传输层。另外,在阴极及电子传输层之间引入薄膜电子注入层,用于减少电子注入障碍并提高有机EL装置性能。现有的电洞注入层材料为具有低功函数的金属卤化物或金属氧化物,比如:LiF、LiQ、MgO或Li2O。
另一方面,在制作有机EL装置之后,通过使用PR650光谱扫描光谱仪量测EL光谱及CIE坐标。此外,电流/电压、发光/电压及产率/电压特征都使用吉时利(Keithley)2400可编程电压电流源来检测。上述设备在室温(约25℃)及大气压下操作。
实施例5
使用与上述一般方法类似的程序,生产具有下列装置结构的有机EL装置(参阅图1)。有机EL装置包含,透明电极6~金属电极14,其之间依序分别为沉积在透明电极6上的电洞注入层7,沉积在电洞注入层7上的电洞传输层8,沉积在电洞传输层8上的电子阻挡层9,沉积在电子阻挡层9上的发光层10,沉积在发光层10上的电洞阻挡层11,沉积在电洞阻挡层11上的电子传输层12,沉积在电子传输层12上的电子注入层13,以及沉积在电子注入层13上的金属电极14。装置:ITO/HAT-CN(20nm)/HT1(110nm)/EB2(5nm)/主体+10%~30%dopant(30nm)/HBM(10nm)/ETM doped 40%LiQ(35nm)/LiQ(1nm)/Al(160nm)有机EL装置的I-V-B(1000nits亮度时)的测试报告结果如表1所示。
表1
在上述有机EL装置测试报告的优选实施例中(参阅表1),我们公开了本发明中具有式(1)或式(2)结构的延迟荧光化合物作为发光层及/或电子传输层及/或电洞阻挡层的发光主体及/或有机EL器件装置的发光层的延迟荧光(TADF)材料时,本发明的有机EL装置的性能显现比有机EL材料现有技术的更好。尤其是,本发明中使用二氢吲哚咔唑骨架(比如C4及C8)用作有机EL装置的延迟荧光化合物时,显现出了比先前技术中使用咔唑核(比如CCQ)更好的效率。
总而言之,本发明提供了一种延迟荧光化合物,其可作为发光层及/或电子传输层及/或电洞阻挡层的磷光发光主体及/或作为有机EL装置的发光层的延迟荧光材料。所述延迟荧光化合物的结构由下式(1)或式(2)表示:
其中,D1及D2中的至少一个独立选自由式(3)至式(5)所示的基团:
其中,L1及L2独立选自单键、具有6到30个环碳原子的取代或未取代的亚芳基或具有3到30个环碳原子的取代或未取代的杂亚芳基;X选自氧原子、硫原子及硒原子;p表示0到4的整数;Z为包含选自由O、S、C(R7)(R8)、NR9及Si(R10)(R11)组成的原子或基团的二价桥;Y1至Y6独立氮原子或C(Rs),且各个Rs独立选自氢原子、苯基、具有1到30个碳原子的取代或未取代的烷基、具有6到30个碳原子的取代或未取代的芳基;R1至R12独立选自氢原子、卤化物、具有1到30个碳原子的取代或未取代的烷基、具有6到30个碳原子的取代或未取代的芳基、具有6到30个碳原子的取代或未取代的芳烷基及具有3到30个碳原子的一取代或未取代的杂芳基。
以上这些实施例仅是范例性的,并不对本发明的范围构成任何限制。本领域技术人员应该理解的是,在不偏离本发明的精神和范围下可以对本发明技术方案的细节和形式进行修改或替换,但这些修改和替换均落入本发明的保护范围内。
Claims (18)
1.一种延迟荧光化合物,其特征在于,其结构由下式(1)或式(2)表示:
其中,D1及D2中的至少一个独立选自由式(3)至式(5)所示的基团:
其中,L1及L2独立选自单键、具有6到30个环碳原子的取代或未取代的亚芳基或具有3到30个环碳原子的取代或未取代的杂亚芳基;X选自氧原子、硫原子及硒原子;p表示0到4的整数;Z为包含选自由O、S、C(R7)(R8)、NR9及Si(R10)(R11)组成的原子或基团的二价桥;Y1至Y6独立选自氮原子或C(Rs),且各个Rs独立选自氢原子、苯基、具有1到30个碳原子的取代或未取代的烷基、具有6到30个碳原子的取代或未取代的芳基;R1及R12独立选自氢原子、卤化物、具有1到30个碳原子的取代或未取代的烷基及具有6到30个碳原子的取代或未取代的芳基、具有6到30个碳原子的取代或未取代的芳烷基或具有3到30个碳原子的一取代或未取代的杂芳基。
2.如权利要求1所述的延迟荧光化合物,其特征在于,L1及L2的结构由下式(6)表示:
其中,Z1至Z5独立选自氮原子或C(Rs),且各个Rs独立选自氢原子、苯基、具有1到30个碳原子的取代或未取代的烷基及具有6到30个碳原子的取代或未取代的芳基。
3.如权利要求1所述的延迟荧光化合物,其特征在于,该延迟荧光化合物的单重态能量与该延迟荧光化合物的三重态能量之间的差异小于0.25eV。
4.如权利要求1所述的延迟荧光化合物,其特征在于,具有式(1)或式(2)结构的该化合物为一发光材料。
5.如权利要求4所述的发光材料,其特征在于,该发光材料发出延迟荧光。
6.一种有机电致发光装置,其特征在于,包含由阴极及阳极组成的一对电极对,且其中该对电极对之间至少包含一层发光层、一层或多层有机薄膜层,其中该发光层、该有机薄膜层其中之一或二者包含如权利要求1所述该延迟荧光化合物。
7.如权利要求6所述的有机电致发光装置,其特征在于,该延迟荧光化合物的单重态能量与该延迟荧光化合物的三重态能量之间的差异小于0.25eV。
8.如权利要求6所述的有机电致发光装置,其特征在于,该发光层包括该延迟荧光化合物。
9.如权利要求6所述的有机电致发光装置,其特征在于,包括具有式(1)或式(2)结构的该延迟荧光化合物的该发光层为一延迟荧光主体材料。
10.如权利要求6所述的有机电致发光装置,其特征在于,包括具有式(1)或式(2)结构的该延迟荧光化合物的该发光层为一延迟荧光掺杂材料。
11.如权利要求6所述的有机电致发光装置,其特征在于,该发光层包括该第二荧光掺杂材料。
12.如权利要求6所述的有机电致发光装置,其特征在于,该发光层包括该第二荧光主体材料。
13.如权利要求6所述的有机电致发光装置,其特征在于,包括具有式(1)或式(2)结构的该延迟荧光化合物的该发光层为一磷光主体材料。
14.如权利要求6所述的有机电致发光装置,其特征在于,包括具有式(1)或式(2)结构的该延迟荧光化合物的该有机薄膜层为一电洞阻挡材料。
15.如权利要求6所述的有机电致发光装置,其特征在于,包括具有式(1)或式(2)结构的该延迟荧光化合物的该有机薄膜层为一电子传输层材料。
16.如权利要求6所述的有机电致发光装置,其特征在于,该装置为一有机发光装置。
17.如权利要求6所述的有机电致发光装置,其特征在于,该装置为一发光面板。
18.如权利要求6所述的有机电致发光装置,其特征在于,该装置为一背光面板。
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CN109369684A (zh) * | 2018-11-01 | 2019-02-22 | 华东师范大学 | 一类电子供体-受体-供体荧光分子及其制备方法和应用 |
CN109659442A (zh) * | 2018-12-13 | 2019-04-19 | 云谷(固安)科技有限公司 | 一种有机电致发光器件和显示装置 |
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CN111378437A (zh) * | 2018-12-26 | 2020-07-07 | 创王光电股份有限公司 | 有机电致发光化合物及包含此化合物的有机电致发光装置 |
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