CN107502340A - 延迟荧光化合物及使用其的有机电致发光装置 - Google Patents
延迟荧光化合物及使用其的有机电致发光装置 Download PDFInfo
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- CN107502340A CN107502340A CN201710641150.4A CN201710641150A CN107502340A CN 107502340 A CN107502340 A CN 107502340A CN 201710641150 A CN201710641150 A CN 201710641150A CN 107502340 A CN107502340 A CN 107502340A
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- delayed fluorescence
- electroluminescent device
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- organnic electroluminescent
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- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- OSCBARYHPZZEIS-UHFFFAOYSA-N phenoxyboronic acid Chemical class OB(O)OC1=CC=CC=C1 OSCBARYHPZZEIS-UHFFFAOYSA-N 0.000 description 1
- 238000001296 phosphorescence spectrum Methods 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000000103 photoluminescence spectrum Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- SDLBJIZEEMKQKY-UHFFFAOYSA-M silver chlorate Chemical compound [Ag+].[O-]Cl(=O)=O SDLBJIZEEMKQKY-UHFFFAOYSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 238000001161 time-correlated single photon counting Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical compound C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- 238000001392 ultraviolet--visible--near infrared spectroscopy Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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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在有机电致发光(有机EL)装置中的应用,本发明的电致发光(有机EL)装置具有良好的性能表现。
Description
技术领域
本发明涉及一种化合物及使用该化合物在有机电致发光(有机EL)装置中的应用。具体而言,本发明涉及一种具有通式(1)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(有机EL)装置因其高照度、低重量、超薄外型、无背光的自照明、高对比度、制造简单及反应时间快速而广泛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)及史帝芬凡斯莱克(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(HTL)、发光层(EML)、电子传输层(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 molecularorbital,LUMO)中,且电洞将从阳极注入最高占用分子轨域(highest occupied molecularorbital,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,根据电子和电洞自旋组合方式,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。从三重态衰减为自旋禁阻(selfforbidden),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***交叉,从而获得单重态和三重态的发射,以及将电致发光装置的内部量子效率从25%增加到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-ligand charge-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***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利用三重态和单重态激子。磷光有机EL通常在发光层(emitting layer,EML)及电子传输层(electron transport layer,ETL)之间需要附加电洞阻挡层(holeblocking layer,HBL),或在发光层(EML)及电洞传输层(hole transport layer,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,使用于发光层中磷光主体材料之,对于工业实务使用而言,在半衰期、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它有机薄膜层(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延长半衰期、提高效率及显示极佳性能,我们使用2,3-二苯基吡啶并[3,4-b]吡嗪(2,3-diphenylpyrido[3,4-b]pyrazine)骨架作为受体并使用5个及/或8个骨架连接的位置来提供咔唑基(carbazole group)、二咔唑基(bicarbazole group)、二氢吲哚咔唑基(dihydroindolocarbazole group)、二氢咔唑基(dihydroindenocarbazole group)、吩噻嗪基(phenothiazine group)、吩基(phenoxazine group)、二氢吖基(dihydroacridinegroup)、二氢化基(dihydrophenazine group)取代,以完成延迟荧光化合物的通式(1)。先前专利US7601435、US20100239339A1、WO2015099486、WO2016013875公开了喹喔啉(quinoxaline)相关化合物并在喹喔啉核的6及7的位置中引入取代基。P.布罗顿(P.Brogdon)等人公布了用于最高效率染料敏化太阳能电池(dye-sensitized solarcell,DSC)装置的基于喹喔啉的染料。(SYNMET 15280No.of Pages 10)。在先前技术中并未有以2,3-二苯基吡啶并[3,4-b]吡嗪(2,3-diphenylpyrido[3,4-b]pyrazine)骨架作为有机EL装置中延迟荧光化合物的受体。
发明内容
根据上述原因,本发明的目的为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。本发明提供了一种具有式(1)结构的延迟荧光化合物,其在有机电致发光(有机EL)装置中用作发光层的延迟荧光材料及/或发光层的磷光发光主体及/或电子传输层及/或电洞阻挡层,该等层具有良好的电荷载体迁移率及极佳的操作耐久性,可降低驱动电压及能耗,增加有机EL装置的效率及半衰期,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式如式(1)所示
其中,D1及D2单独选自式(2)至式(6):
其中,L表示单键、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;m表示0到5的整数;n表示0到2的整数;p表示0到4的整数;q表示0到7的整数;r表示0到8的整数;X为包含选自O、S、C(R14)(R15)、NR16及Si(R17)(R18)组成的原子或基团的二价桥;Y1表示氮原子或C(Rs),且各个Rs单独表示氢原子、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R2单独选自氢原子、卤化物、硝基、吡啶、吡嗪、嘧啶、三嗪、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;而R3到R18单独选自氢原子、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烷基及具有3到30个碳原子的取代或未取代的杂芳基。
上列详细说明为针对本发明之一可行实施例的具体说明,但该实施例并非用以限制本发明的权利要求范围,凡未脱离本发明主旨所进行的等效实施或变更,均应包含于本发明的权力要求范围中。
综上所述,本发明不但在空间型态上确属创新,并能较现有技术增进上述多项功效,应已充分符合新颖性及创造性的法定发明专利要素,爰依法提出申请,恳请贵局核准本件发明专利申请案,以励发明,至感德便。
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C4的延迟荧光特性的瞬时衰变固化。
图3为化合物Q的延迟荧光特性的瞬时衰变固化。
图4为化合物如C4的UV-Vis(nm)及PL(nm)图。
图5为对比化合物如Q的UV-Vis(nm)及PL(nm)图。
【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
下面结合具体实施例及附图来进一步描述本发明,本发明的优点和特点将会随着描述而更为清楚。但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。
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式如式(1)所示:
其中,D1及D2单独选自式(2)至式(6):
其中,L表示单键、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;m表示0到5的整数;n表示0到2的整数;p表示0到4的整数;q表示0到7的整数;r表示0到8的整数;X为包含选自由O、S、C(R14)(R15)、NR16及Si(R17)(R18)组成的原子或基团的二价桥;Y1表示氮原子或C(Rs),且各个Rs单独表示氢原子、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R2单独选自氢原子、卤化物、硝基、吡啶、吡嗪、嘧啶、三嗪、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;而R3到R18单独选自氢原子、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烷基及具有3到30个碳原子的取代或未取代的杂芳基。
在本发明的一个实施例中,根据上述延迟荧光化合物式(1),其中,L1及L2的结构式如式(7)所示:
其中,Z1及Z5单独表示氮原子或C(Rs),且各个Rs单独表示氢原子、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。
在本本发明的实施例中,一些延迟荧光化合物的结构式如下式所示:
本发明的延迟荧光化合物的详细制备方法将由以下示例性实施例阐明,但本发明不限于这些示例性实施例。实施例1至实施例6为本发明中延迟荧光化合物的制备实施例。实施例10至11为有机EL装置及IVB的制作及有机EL装置的测试报告。
实施例1化合物C4的合成
5,8-二溴-2,3-二苯基吡啶并[3,4-b]吡嗪(5,8-dibromo-2,3-diphenylpyrido[3,4-b]pyrazine)的合成:
于100℃下将10g(37.5mmol)2,5-二溴吡啶-3,4-二胺(2,5-dibromopyridine-3,4-diamine)、8.66g(41.2mmol)苯偶酰(benzil)、200ml醋酸的混合物加热2小时。使所得混合物冷却至室温,随后过滤得到黄色固体。产率(11g,66.7%)。
1H NMR(CDCl3,400MHz):化学位移(ppm)8.50(s,1H),7.41-7.51(m,10H)。
9,9'-(2,3-二苯基吡啶并[3,4-b]吡嗪-5,8-二基)双(9H-咔唑)(9,9'-(2,3-diphenylpyrido[3,4-b]pyrazine-5,8-diyl)bis(9H-carbazole))(C4)的合成:
将5g(11.3mmol)的5,8-二溴-2,3-二苯基吡啶并[3,4-b]吡嗪(5,8-dibromo-2,3-diphenylpyrido[3,4-b]pyrazine)及5.69g(34mmol)的咔唑(carbazole)、2.16g(11.3mmol)的CuI、7.39g(22.6mmol)的Cs2CO3、2.27g(8.6mmol)的18-冠-6(18-crown-6)以及80ml的1,2-二氯苯(1,2-dichlorobenzene)的混合物除气并置于氮气中,随后加热回流12小时。在完成反应之后,将混合物冷却至室温。加入250ml的甲醇,随后过滤并使用甲醇清洗,得到红色固体。产率(4.5g,64.7%)。
1H NMR(CDCl3,400MHz):化学位移(ppm)8.62(s,1H),、8.58(d,2H),8.15(d,2H)、7.92(d,2H)、7.65(d,2H)、7.41-7.51(m,12H)、7.25-7.33(m,6H)。MS(m/z,EI+):613.5
实施例2化合物C8的合成
9,9'-(3,3'-(2,3-二苯基吡啶并[3,4-b]吡嗪-5,8-二基)双(3,1-亚苯基))双(9H-咔唑)(9,9'-(3,3'-(2,3-diphenylpyrido[3,4-b]pyrazine-5,8-diyl)bis(3,1-phenylene))bis(9H-car bazole)(C8)的合成:
将5g(11.3mmol)的5,8-二溴-2,3-二苯基吡啶并[3,4-b]吡嗪(5,8-dibromo-2,3-diphenylpyrido[3,4-b]pyrazine)及7.16g(24.9mmol)的3-(9H-咔唑-9-基)苯基硼酸(3-(9H-carbazol-9-yl)phenylboronic acid)、0.13g(0.11mmol)的Pd(PPh3)4、14.1ml的2MNa2CO3(aq)、50ml的EtOH以及150ml的甲苯的混合物除气并置于氮气中,随后于100℃下加热12小时。在完成反应之后,将混合物冷却至室温。加入250ml的甲醇,随后过滤并使用甲醇清洗,得到红色固体。产率(5.04g,59%)。
MS(m/z,EI+):765.5
实施例3化合物C17的合成
9,9',9”,9”'-(5,5'-(2,3-二苯基吡啶并[3,4-b]吡嗪-5,8-二基)双(苯5,3,1-三基))四(9H-咔唑)(9,9',9”,9”'-(5,5'-(2,3-diphenylpyrido[3,4-b]pyrazine-5,8-diyl)bis(benzene-5,3,1-triyl))tetrakis(9H-carbazole))(C17)的合成:
使用如实施例2中的合成方法,将9,9'-(5-(4,4,5,5-四甲基-1,3,2-二氧杂环戊硼烷-2-基)-1,3-亚苯基)双(9H-咔唑)(9,9'-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-phenylene)bis(9H-carbazole))取代3-(9H-咔唑-9-基)苯基-硼酸(3-(9H-carbazol-9-yl)phenyl-boronic acid),得到所需化合物9,9',9”,9”'-(5,5'-(2,3-二苯基吡啶并[3,4-b]吡嗪-5,8-二基)双(苯5,3,1-三基))四(9H-咔唑)(9,9',9”,9”'-(5,5'-(2,3-diphenylpyrido[3,4-b]pyrazine-5,8-diyl)bis(benzene-5,3,1-triyl))tetrakis(9H-carbazole))(C17)。
MS(m/z,EI+):1096.4
实施例4化合物C25的合成
9,9'-(2,3-二苯基吡啶并[3,4-b]吡嗪-5,8-二基)双(6-(9H-咔唑-9-基)-9H-3,9'-二咔唑)(9,9'-(2,3-diphenylpyrido[3,4-b]pyrazine-5,8-diyl)bis(6-(9H-carbazol-9-yl)-9H-3,9'-bicarbazole))(C25)的合成:
使用如实施例1中的合成方法,6-(9H-咔唑-9-基)-9H-3,9'-二咔唑(6-(9H-carbazol-9-yl)-9H-3,9'-bicarbazole)取代咔唑(carbazole),得到9,9'-(2,3-二苯基吡啶并[3,4-b]吡嗪-5,8-二基)双(6-(9H-咔唑-9-基)-9H-3,9'-二咔唑)(9,9'-(2,3-diphenylpyrido[3,4-b]pyrazine-5,8-diyl)bis(6-(9H-carbazol-9-yl)-9H-3,9'-bicarbazole))(C25)。
MS(m/z,EI+):1274.8
实施例5化合物C38的合成
12,12'-(3,3'-(2,3-二苯基吡啶并[3,4-b]吡嗪-5,8-二基)双(3,1-亚苯基))二(11-苯基-11,12-二氢吲哚并[2,3-a]咔唑)(12,12'-(3,3'-(2,3-diphenylpyrido[3,4-b]pyrazine-5,8-diyl)bis(3,1-phenylene))bis(11-phenyl-11,12-dihydroindolo[2,3-a]carbazole))(C38)的合成:
使用如实施例2中的合成方法,11-苯基-12-(3-(4,4,5,5-四甲基-1,3,2-二氧硼杂环戊烷-2-基)苯基-11,12-二氢吲哚并[2,3-a]咔唑(11-phenyl-12-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-11,12-dihydroindolo[2,3-a]carbazole)取代3-(9H-咔唑-9-基)苯基硼酸(3-(9H-carbazol-9-yl)phenylboronicacid),得到所需化合物12,12'-(3,3'-(2,3-二苯基吡啶并[3,4-b]吡嗪-5,8-二基)双(3,1-亚苯基))双(11-苯基-11,12-二氢吲哚并[2,3-a]咔唑)(12,12'-(3,3'-(2,3-diphenylpyrido[3,4-b]pyrazine-5,8-diyl)bis(3,1-phenylene))bis(11-phenyl-11,12-dihydroindolo[2,3-a]carbazole))(C38)。
MS(m/z,EI+):1096.6
实施例6化合物C67的合成
10,10'-(2,3-二苯基吡啶并[3,4-b]吡嗪-5,8-二基)双(10H-吩恶嗪)(10,10'-(2,3-diphenylpyrido[3,4-b]pyrazine-5,8-diyl)bis(10H-phenoxazine))(C67)的合成。
使用如实施例1中的合成方法,10H-吩恶嗪(10H-phenoxazine)取代咔唑(carbazole),得到所需化合物10,10'-(2,3-二苯基吡啶并[3,4-b]吡嗪-5,8-二基)双(10H-吩恶嗪)(10,10'-(2,3-diphenylpyrido[3,4-b]pyrazine-5,8-diyl)bis(10H-phenoxazine))(C67)。
MS(m/z,EI+):645.3
延迟荧光化合物光物理学特性的量测方法
光物理学特征:在用于之后的研究之前,将合成的化合物在高真空下通过温度梯度升华进行纯化。在具有<10-6torr本底压力的真空室内,于石英基底上以1-2A/sec的速度通过热蒸发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分光光度仪(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光度仪(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光度仪来检测。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。透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光度仪在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***10-ms延迟时间。通过使用具有荧光寿命***的时间相关单光子计数技术(FluoroCube,Horiba Jobin Yvon Inc.)及来自UV发光二极管的纳秒(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***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0.1M n-Bu4NPF6(TBAPF6)在CH2Cl2中作为支持电解质,扫描速率为100mV s-1,通过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/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及图3表示C4及对比化合物的延迟荧光于甲苯溶液的瞬时衰减曲线的测量值。图4及图5表示C4及对比化合物的光激荧光发射光谱的测量值。
生产有机EL装置的一般方法
提供抗性为9~12ohm/square及厚度为120~160nm的氧化铟锡(ITO)涂层玻璃(之后以ITO为基材),并在超声波浴(例如:洗涤剂、去离子水)中进行几步骤的清洗。在对有机层进行气相沉积之前,通过UV及臭氧进一步处理清洁的ITO基材。ITO基材的所有预处理过程都在洁净室(class 100)内进行。
将这些有机层在高真空单元(10-7Torr)中通过气相沉积按顺序施加在ITO基材上,比如:电阻加热的石英船。使用石英晶体监视器精确监控或设定每层的厚度及气相沉积速率(0.1~0.3nm/sec)。如上所述,各层包含不止一种化合物,意即,通常为掺杂有掺杂剂材料的主体材料。这是通过两个或更多来源的共蒸发来实现的。
在有机EL装置中,使用二吡嗪并[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)作为电洞注入层,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)作为电洞传输层,N-(联苯-4-基)-9,9-二甲基-N-(4'-苯基联苯-4-基)-9H-芴-2-胺(N-(biphenyl-4-yl)-9,9-dimethyl-N-(4'-phenylbiphenyl-4-yl)-9H-fluoren-2-amine)(EB2)作为电子阻挡层,H1用作本发明磷光主体及延迟荧光主体的对照组或标准品。化学结构如下:
本发明中制备的下列延迟荧光实施例可作为延迟荧光掺杂剂、电洞阻挡材料或电子传输材料,并通过有机EL装置进行测试。本发明中,以化合物Q(CCQ)作为该延迟荧光掺杂剂的对照组。
有机铱络合物广泛用作发光层的磷光掺杂剂,其中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”-(1,3,5-三苯基)-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用作电洞阻挡材料(HBM),而2-(10,10-二甲基-10H-茚并[2,1-b]苯并菲-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,在有机EL装置中与8-羟基喹啉-锂(8-hydroxyquinolato-lithium)(LiQ)共沉积。现有技术中用于生产标准有机EL装置的其它OLED材料与及本发明的材料结构如下:
有机EL装置一般包含经过热蒸发作为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,能够用于减少电子注入障碍并提高有机EL装置性能。现有技术中的电子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,透过使用PR650光谱扫描光谱仪量测EL光谱及CIE坐标。此外,使用Keithley 2400可编程电压电流源来检测电流/电压、发光/电压及产率/电压。上述装置在室温(约25℃)及大气压下进行操作。
实施例10
使用与上述生产有机EL装置的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)。装置:ITO/HAT-CN(20nm)/HT1(110nm)/EB2(5nm)/主体+10%~30%掺杂剂(30nm)/HBM(10nm)/ETM掺杂40%LiQ(35nm)/LiQ(1nm)/Al(160nm)。有机EL装置的I-V-B(于1000nits亮度时)的测试报告如表1所示。
表1
在上述有机EL装置测试报告的最佳实施例中(参阅表1),我们提供了本发明中具有通式(1)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装置的发光层的延迟荧光(TADF)材料时,呈现出比现有技术中有机EL材料更良好的性能。尤其是,2,3-二苯基吡啶并[3,4-b]吡嗪(2,3-diphenylpyrido[3,4-b]pyrazine)骨架(比如C4)用作有机EL装置的延迟荧光化合物时,呈现了比喹喔啉核(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式如式(1)所示:
其中,D1及D2单独选自式(2)至式(6):
其中,L表示单键、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;m表示0到5的整数;n表示0到2的整数;p表示0到4的整数;q表示0到7的整数;r表示0到8的一整数;X为包含选自O、S、C(R14)(R15)、NR16及Si(R17)(R18)组成的原子或基团的二价桥,Y1表示氮原子或C(Rs),且各个Rs单独表示氢原子、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R2单独选自氢原子、卤化物、硝基、吡啶、吡嗪、嘧啶、三嗪、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;而R3到R18单独选自氢原子、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个碳原子的一取代或未取代的芳烷基及具有3到30个碳原子的取代或未取代的杂芳基。
Claims (18)
1.一种延迟荧光化合物,其特征在于,其结构式如式(1)所示:
其中,D1及D2单独选自式(2)至式(6):
其中,L表示单键、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芳基;m表示0到5的整数;n表示0到2的整数;p表示0到4的整数;q表示0到7的整数;r表示0到8的整数;X为包含选自O、S、C(R14)(R15)、NR16及Si(R17)(R18)组成的原子或基团的二价桥;Y1表示氮原子或C(Rs),且各个Rs单独表示氢原子、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个碳原子的一取代或未取代的芳基;R1及R2单独选自氢原子、卤化物、硝基、吡啶、吡嗪、嘧啶、三嗪、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;而R3到R18单独选自氢原子、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烷基及具有3到30个碳原子的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的结构式如式(7)所示:
其中,Z1及Z5单独表示氮原子或C(Rs),且各个Rs单独表示氢原子、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)结构的该化合物为一发光材料。
5.如权利要求4所述的延迟荧光化合物,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,其包含由阴极及阳极组成的一对电极对,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具有一如权利要求1-5任一项所示的延迟荧光化合物。
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及/或该荧光化合物。
9.如权利要求6所述的有机电致发光装置,其特征在于,其中包括具有式(1)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,其中包括具有式(1)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,该发光层更包括一第二延迟荧光掺杂材料。
12.如权利要求6所述的有机电致发光装置,其特征在于,该发光层更包括一第二延迟荧光主体材料。
13.如权利要求6所述的有机电致发光装置,其特征在于,其中包括具有式(1)结构的该延迟荧光化合物的该发光层为一荧光主体材料。
14.如权利要求6所述的有机电致发光装置,其特征在于,其中包括具有式(1)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,其中包括具有式(1)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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CN109796451A (zh) * | 2019-02-18 | 2019-05-24 | 中国科学院化学研究所 | 一种以萘啶作为电子受体的多色热激活延迟荧光材料及其制备方法与应用 |
CN111533736A (zh) * | 2020-04-15 | 2020-08-14 | 苏州久显新材料有限公司 | 氮杂萘类衍生物、其合成方法及其电子器件 |
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