CN107011183A - 新颖化合物及包含其的有机电子装置 - Google Patents

新颖化合物及包含其的有机电子装置 Download PDF

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CN107011183A
CN107011183A CN201710061447.3A CN201710061447A CN107011183A CN 107011183 A CN107011183 A CN 107011183A CN 201710061447 A CN201710061447 A CN 201710061447A CN 107011183 A CN107011183 A CN 107011183A
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heterocyclic radical
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CN107011183B (zh
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廖良玓
谢淑珠
陈济中
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Shanghai Nichem Fine Chemical Co Ltd
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Nichem Fine Technology Co Ltd
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Abstract

如以下化学式(I)所表示的新化合物：其中，Ar1、Ar2、Ar3、Ar4、L、Q、G、n1、n2、m1、m2及q如说明书的定义。此外，本发明也公开了一有机电子装置，其中的有机层包含本发明新颖化合物。

Description

新颖化合物及包含其的有机电子装置
技术领域
本发明涉及一种新颖化合物以及使用其的有机电子装置。
背景技术
有机发光装置(OLED device)已公知最初是由Eastman Kodak公司提出通过真空蒸镀法所发明的。Kodak公司的Tang及VanSlyke将电子传递材料如Alq3设置在表面上形成有一芳香族二胺有机层的透明氧化铟锡玻璃(缩写为ITO)之上，接着气相沉积金属电极在Alq3层之上后完成有机电致发光(EL)装置。因为具有高亮度、反应速度快、重量轻、小巧、色彩真实、无视角差别、不须使用任何LCD背光板以及低耗能的缘故，上述的有机EL装置现在变成新一代的照明装置或显示装置。
近年来，一些如电子传输层及空穴传输层的中间层被添加在阴极及阳极之间以增加OLED的电流效率及功率效率。例如，一种如图1所示的有机发光二极体(OLED)1’被设计成包含有：一阴极11’、一电子注入层13’、一发光层14’、一空穴传输层16’及一阳极18’。
近年来，为了有效率的增加OLED的发光性能，OLED制造商及研究人员已努力地开发不同的化合物，作为OLED的材料。然而，尽管已经开发了各种化合物，目前磷光的OLED仍然无法有优异的发光效率及装置生命期，据此，基于用于OLED的常规或商业材料仍有缺点，本申请的发明人已作出了巨大的努力以做出创造性的研究，并最终提供了新颖化合物供OLED使用。
发明内容
本发明的目的在于提供一种新颖化合物和包含其的有机电子装置。
根据一或多个实施例，化合物由以下化学式(I)所表示：
其中，
Ar1、Ar2、Ar3和Ar4各自独立为氢、氘、经取代或未经取代C1-C20的烷基、经取代或未经取代C6-C40的芳基、经取代或未经取代C1-C40的杂环基、或经取代或未经取代的胺基；或Ar1和Ar2与其所键结的N原子一起形成经取代或未经取代C1-C40的杂环基；或Ar3和Ar4与其所键结的N原子一起形成经取代或未经取代C1-C40的杂环基；
L和Q各自独立为经取代或未经取代C6-C40的亚芳基；
G为氘、经取代或未经取代C1-C20的烷基、经取代或未经取代C6-C40的芳基、经取代或未经取代C1-C40的杂环基或-NR1R2；
R1和R2各自独立为氢、氘、经取代或未经取代C1-C20的烷基、经取代或未经取代C6-C40的芳基，或经取代或未经取代C1-C40的杂环基；
n1和n2各自独立为0或1；
m1和m2各自独立为0、1或2，且m1和m2不同时为0；以及
q为0、1或2。
根据一或多个实施例，一有机电子装置包含：一第一电极；一第二电极；以及一有机层，设置于该第一电极与该第二电极间，其中该有机层包含上述化学式(I)的化合物。
本发明提供一种新颖化合物，当本发明化合物用于有机电子装置时，可以提升该有机电子装置的效率，尤其是，当本发明的新颖化合物作为有机发光装置的材料时，可以进一步提升该有机发光装置的发光效率。
附图说明
图1为现有技术的OLED装置示意图；
图2为本发明的OLED装置示意图；
图3为本发明的有机太阳能电池装置示意图；
图4为本发明的化合物(1)(SGM 134)的NMR图谱；
图5为本发明的化合物(2)(SGM 137)的NMR图谱；
图6为本发明的化合物(4)(SGM 423)的NMR图谱；
图7为本发明的化合物(7)(SGM 135)的NMR图谱；
图8为本发明的化合物(8)(SGM 138)的NMR图谱；
图9为本发明的化合物(10)(SGM 422)的NMR图谱；
图10为本发明的化合物(11)(SGM 565)的NMR图谱；
图11为本发明的化合物(12)(SGM 578)的NMR图谱；
图12为本发明的化合物(31)(SGM 564)的NMR图谱；
图13为本发明的化合物(13)(SGM 136)的NMR图谱；
图14为本发明的化合物(14)(SGM 139)的NMR图谱；
图15为本发明的化合物(15)(SGM 171)的NMR图谱；
图16为本发明的化合物(20)(SGM 567)的NMR图谱；
图17为本发明的化合物(21)(SGM 568)的NMR图谱；
图18为本发明的化合物(30)(SGM 557)的NMR图谱；
图19为本发明的化合物(32)(SGM 584)的NMR图谱；
图20为本发明的化合物(33)(SGM 594)的NMR图谱。
【附图标记说明】
1’ 有机发光二极体
11 基板
12、18’ 阳极
13、13’ 空穴注入层
14、16’ 空穴传输层
15、14’ 发光层
16 电子传输层
17 电子注入层
18、11’ 阴极
21 第一电极
22 第二电极
23 有机层
具体实施方式
以下将详细描述本发明。本发明以说明性的方式对发明进行描述，所使用的术语应被理解为旨在描述而不在限制。对于本发明的许多修饰和改变根据教示是可能的。因此，在所附权利要求的范围内，本发明或许可以通过不同于具体描述的方式被实施。
化合物
根据一例示性实施例的化合物可以下列化学式(I)所表示。
在化学式(I)中，Ar1、Ar2、Ar3和Ar4可各自独立为氢、氘、经取代或未经取代C1-C20的烷基、经取代或未经取代C6-C40的芳基、经取代或未经取代C1-C40的杂环基、或经取代或未经取代的胺基；或Ar1和Ar2与其所键结的N原子一起可形成经取代或未经取代C1-C40的杂环基；或Ar3和Ar4与其所键结的N原子一起可形成经取代或未经取代C1-C40的杂环基；
L和Q可各自独立为经取代或未经取代C6-C40的亚芳基；
G可为氘、经取代或未经取代C1-C20的烷基、经取代或未经取代C6-C40的芳基、经取代或未经取代C1-C40的杂环基或-NR1R2；
R1和R2可各自独立为氢、氘、经取代或未经取代C1-C20的烷基、经取代或未经取代C6-C40的芳基、或经取代或未经取代C1-C40的杂环基；
n1和n2可各自独立为0或1；
m1和m2可各自独立为0、1或2，且m1和m2不同时为0；以及
q可为0、1或2。
根据一实施例，Ar1、Ar2、Ar3和Ar4可各自独立为经取代或未经取代C6-C40的芳基、或经取代或未经取代C1-C40的杂环基；或Ar1和Ar2与其所键结的N原子一起可形成经取代或未经取代C1-C40的杂环基；或Ar3和Ar4与其所键结的N原子一起可形成经取代或未经取代C1-C40的杂环基。优选地，Ar1、Ar2、Ar3和Ar4各自独立为经取代或未经取代C6-C40的芳基、或经取代或未经取代C1-C40的杂芳基；或Ar1和Ar2与其所键结的N原子一起形成经取代或未经取代C1-C40的杂芳基；或Ar3和Ar4与其所键结的N原子一起形成经取代或未经取代C1-C40的杂芳基。
根据一实施例，Ar1、Ar2、Ar3和Ar4可各自独立为经取代或未经取代的苯基、经取代或未经取代的联苯基、经取代或未经取代的联三苯基、经取代或未经取代的茀基、经取代或未经取代的三苄基氧杂环庚烯基(tribenzyloxepinyl)、经取代或未经取代的二苯并呋喃基(dibenzofuranyl)、经取代或未经取代的二苯并噻吩基(dibenzothiofuranyl)、经取代或未经取代的萘基、或经取代或未经取代的三苄基-氮呯基(tribenzyl-azepinylgroup)。优选地，Ar1、Ar2、Ar3和Ar4各自独立为未经取代的苯基、经烷基取代的苯基、未经取代的联苯基、未经取代的联三苯基、未经取代的茀基、经烷基取代的茀基、未经取代的三苄基氧杂环庚烯基、未经取代的二苯并呋喃基，或未经取代的萘基。
根据一实施例，m1可为1；且m2可为0或1。根据另一实施例，m1可为1，而m2可为0。根据再一实施例，m1可为1，而m2可为1。
根据一实施例，m1可为1；m2可为0；且Ar1和Ar2与其所键结的N原子一起可形成经取代或未经取代C1-C40的杂芳基。优选地，Ar1和Ar2与其所键结的N原子一起形成未经取代的三苄基-氮呯基(tribenzyl-azepinyl group)。
根据一实施例，当m1及m2同时不为0，–Ln1-NAr1Ar2及–Qn2-NAr3Ar4可相同。
根据一实施例，m1及m2同为1，且–Ln1-NAr1Ar2及–Qn2-NAr3Ar4可相同。
根据一实施例，L和Q可以各自独立为经取代或未经取代的亚苯基、亚联苯基或亚萘基。优选地，L和Q各自独立为未经取代的亚苯基。
根据一实施例，q可为0或1。
当q为1时，G可以为经取代或未经取代C6-C40的芳基、或经取代或未经取代C1-C40的杂环基或-NR1R2，其中R1和R2各自独立为经取代或未经取代C6-C40的芳基。优选地，G为包含一氮原子的经取代或未经取代C1-C40的杂芳基或-NR1R2，其中R1和R2为相同的经取代或未经取代的苯基、联苯基或亚萘基。更优选地，G为未经取代的吡啶基或-NR1R2，其中R1和R2为未经取代的苯基。
根据一实施例，G、–Ln1-NAr1Ar2及–Qn2-NAr3Ar4可相同。例如，当m1为1而m2为0，G及–Ln1-NAr1Ar2可相同。
根据另一实施例，G、–Ln1-NAr1Ar2及–Qn2-NAr3Ar4可不同。例如，当m1为1而m2为0，G及–Ln1-NAr1Ar2可不同。
根据一实施例，该化学式(I)所示的化合物可为以下化学式(I-1)至(I-18)任一所表示：
其中，化学式(I-1)至(I-18)中的Ar1、Ar2、Ar3、Ar4、L、Q、G、n1和n2与以上描述相同。
根据一实施例，–Ln1-NAr1Ar2及–Qn2-NAr3Ar4可各自独立选自由下列所组成的群组：
以及其中，*代表键结位置；Ra及Rb各自独立为C1-20烷基；以及x及y各自独立为1或2。在此，Ra及Rb可相同。x及y可相同。Ra及Rb的例子可为甲基、乙基或丙基。此外，n1或n2可为0。
根据一实施例，n1为0而n2为1。根据另一实施例，n1为1而n2为1。在此两个实施例中，–Ln1-NAr1Ar2及–Qn2-NAr3Ar4可各自独立选自由下列所组成的群组：
以及其中，*代表键结位置。Ra、Rb、x及y的定义如前所述。于此两个实施例中，L及Q可各自独立为经取代或为取代的C6-C40亚芳基，如亚苯基。
以下，将详细描述化学式(I)的取代基，本发明未定义的取代基表示与本领域已知的定义相同。
在本发明中，该未经取代的烷基可以为线型或支链型，例如包含C1-C20的烷基、C1-C10的烷基或C1-C6的烷基。未经取代的烷基的具体例子包含甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、戊基、新戊基或己基，但不局限于此。在此，该未经取代的烷基至少一个氢原子可以被卤素、烷基、烯基、烷氧基、环烷基、芳基、芳烷基、芳烯基、杂环基、氰基或乙炔基所取代。
在本发明中，该未经取代的芳基是指芳香族烃基，例如可为C6-C40的芳基或C6-C20的芳基。此外，该芳基可为单环、双环、三环或多环芳香族烃基；其中二或多环可以彼此稠合或藉由单一键彼此相联。未经取代的芳基的具体例子包含苯基、联苯基、联三苯基、联四苯基、萘基、蒽基、苯并蒽基(benzanthryl)、菲基(phenanthryl)、稠四苯基(naphthacetyl)、芘基(pyrenyl)、屈基(chrysenyl)、苯并[c]菲基、苯并[g]屈基、三亚苯基、芴基(fluorenyl)、螺环双芴基(spirobifluorenyl)、苯并芴基(benzofluorenyl)或二苯并芴基(dibenzofluorenyl)，但不局限于此。在此，该未经取代的芳基至少一个氢原子可被以上关于烷基描述的相同取代基取代。此外，该亚芳基的定义与以上叙述相同，且不在此详细说明。
在本发明中，该未经取代的杂环基是指非芳香族或芳香族烃基，例如可为C1-C40的杂环基、C2-C20的杂环基或C4-C20的杂环基。此外，该杂环基可为具有至少一选自O、N、及S的杂原子的单环、双环、三环或多环杂芳基或杂环烷基；其中二或多环可以藉由彼此稠合或藉由单一键彼此相联。未经取代的杂环基的具体例子包含吡咯基(pyroryl)、吡嗪基(pyrazinyl)、吡啶基、哌啶基、吲哚基、异吲哚基、咪唑基、苯并咪唑基、呋喃基、恶唑基(ozazolyl)、噻唑基、噻二唑基(thiadiazolyl)、苯并噻唑基、四唑基、恶二唑基(oxadiazolyl)、三吖嗪基(triazinyl)、咔唑基、苯并呋喃基、二苯并呋喃基、二苯并噻吩基(dibenzothiofuranyl)、二苯并苯硫基(dibenzothiophenyl)、喹啉基、异喹啉基、喹喔啉基(quinoxalinyl)、菲唳基(phenantridinyl)、吖啶基(acridinyl)、菲咯啉基(phenanthrolinyl)、吩嗪基(phenazinyl)、啡噻嗪基(phenothiazinyl)、吩恶嗪基(phenoxazinyl)、恶唑基(oxazolyl)、恶二唑基(oxadiazolyl)、呋咱基(furazanyl)、噻吩基(thienyl)、苯并苯硫基(benzothiophenyl)、三苯基氧呯基(tribenzyloxepinyl)、苯硫基(thiophenyl)或苯并恶唑基(benzooxazolyl)，但不局限于此。在此，该未经取代的杂环基至少一氢原子可被以上关于烷基描述的相同取代基取代。
在一实施例中，二或多个芳基或杂环基可以直接彼此交联形成螺环结构，例如，芴基和三苯并-环庚三烯基(tribenzo-cycloheptatrienyl)可彼此交联形成螺环结构。
在本发明中，卤素包含氟、氯、溴和碘；优选为氟或溴。
在本发明中，该未经取代的烷氧基是指上述定义的烷基与氧原子偶合的基团。例如可以包含线型或支链型C1-C10的烷氧基或线型或支链型C1-C6的烷氧基。具体例子包含甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、戊氧基、新戊氧基或己氧基，但不局限于此。在此，该未经取代的烷氧基至少一氢原子可被以上关于烷基描述的相同取代基取代。
在本发明中，该未经取代的环烷基是指具有3-20个碳原子的单价饱和烃环，或3-12个碳原子的单价饱和烃环。未经取代的环烷基的具体例子包含环丙基、环丁基、环戊基、环己基、环庚基或环辛基，但不局限于此。在此，该未经取代的环烷基至少一氢原子可被以上关于烷基描述的相同取代基取代。
在本发明中，该未经取代的烯基可以为线型或支链型，且具有至少一个碳-碳双键。例如可以包含C1-C20的烯基、C1-C10的烯基或C1-C6的烯基。未经取代的烯基的具体例子包含乙烯基、丙烯基、丙亚烯基、烯丙基或1,4-丁二烯，但不局限于此。在此，该未经取代的烯基至少一氢原子可被以上关于烷基描述的相同取代基取代。
化学式(I)所示的化合物可以包含下列化合物(1)至(224)中的任一：
在此，化合物(1)-(224)中的至少一个氢原子可以进一步选择性地被上述取代基取代。
有机电子装置
本发明提供一包含上述化合物的有机电子装置。
在一实施例中，该有机电子装置包含：一第一电极；一第二电极以及一设置于上述第一电极与第二电极的间的有机层，其中，该有机层包含上述化合物中的任一种。
在此，“有机层”是指单层或多层，其设置于有机电子装置的第一电极与第二电极之间。
本发明的有机电子装置的应用包括但不限于有机发光装置、有机太阳能电池装置、有机薄膜晶体管、有机光感测器、平板显示器、电脑显示器、电视、广告牌、室内或室外照明光、室内或室外信号光、抬头显示器、全透明显示器、柔性显示器、激光印表机、电话、手机、平板电脑、笔记本电脑、数码相机、便携式摄像机、取景器、微型显示器、交通工具、大电视墙、剧场或体育场屏幕、信号标志。较佳地，本发明的有机电子装置应用在有机发光装置或有机太阳能电池装置中。
在一实施例中，有机电子装置可为有机发光装置，图2为本发明中的一实施例使用的有机发光装置的示例性结构示意图，如图2所示，该有机发光装置包含：一基板11；一阳极12；一阴极18；以及一有机层包含一空穴注入层13、一空穴传输层14、一发光层15、一电子传输层16和一电子注入层17。然而，本发明并不局限于此。可以在本发明的有机发光装置中形成能够提高有机发光装置的发光效率的其他层，例如一电子阻隔层或一空穴阻隔层。当本发明的有机发光装置进一步包含电子阻隔层时，该电子阻隔层设置于空穴传输层14与发光层15之间。当本发明的有机发光装置进一步包含空穴阻隔层时，该空穴阻隔层设置于电子传输层16与发光层15之间。
在一实施例中，本发明的有机发光装置可以包含一含有上述化合物的空穴传输层。在另一实施例中，本发明的有机发光装置可以包含一含有上述化合物的空穴注入层。在又一实施例中，本发明的有机发光装置可以包含一含有上述化合物的电子阻隔层。然而，本发明并不局限于此。
在一实施例中，发光层可以包含一含有铱或铂的磷光发光材料。在另一实施例中，发光层可以包含一量子点或半导体奈米结晶材料。然而，本发明并不局限于此。
在另一实施例中，有机电子装置可为有机太阳能电池，图3为本发明中的一实施例使用的有机太阳能电池的示例性结构示意图，如图3所示，该有机太阳能电池可包含：一第一电极21；一第二电极22；以及一设置于上述第一电极21与第二电极22之间的有机层23，且有机层23包含上述化合物中的任一种。在此，该有机层23可以作为一载子传输层。
本发明的其他目的、优势及新颖特征可从下面的详细描述结合附图，变得更加清楚。
实施例
以下实施例是为了提供本发明特性的说明，然而本发明并不局限于以下实施例的描述。
除非另有说明，否则以下合成是在保护气体气氛下执行。起始物可以从Aldrich或Alfa购得，或根据文献所揭示的工艺合成。
合成实施例1–中间物A1-A8及其合成
用于制备化学式(I)的化合物的中间物A1-A8列于以下表1中，其中，每个中间物下方的数字表示其CAS编号。
表1–中间物A1-A8
中间物A1-A5
中间物A1-A5从Aldrich或Alfa购买，且CAS编号列于上表。
中间物A6-A8的合成
[流程I]
中间物A6-A8可根据以上流程I来制备。起始物Ar1-NH2(芳基胺)和Br-Ar2(溴芳基)列于下表2中。
简要地，将溴芳基(1.0eq)、芳基胺(1.05eq)、乙酸钯(0.01eq)、1,1'-双(二苯基膦)二茂铁(dppf，0.04eq)、仲丁基氧化钠(NaO-t-Bu，1.5eq)和甲苯的混合物置于压力管中，在氮气下加热至80℃反应12小时，待反应完成后，在真空下移除挥发物，将剩余的溶液以二氯甲烷萃取(3×60mL)，合并有机层以食盐水洗，以硫酸钠干燥并浓缩后得黄色固体，进一步将粗产物以硅胶管柱层析法纯化，使用己烷/二氯甲烷(体积比2:1)作为冲提液。所得产物即中间物A6-A8的分析数据列于下表2中。
表2
合成实施例2–中间物B1-B4及其合成
用于制备化学式(I)的化合物的中间物B1-B4列于以下表3中。
表3–中间物B1-B4
中间物B1的合成
[流程II]
中间物B1可根据以上流程II来制备。
步骤1：中间物B1-1的合成
取3-溴二苯并[a,d]环庚-5-酮(86g，1.0eq)、N-溴琥珀酰亚胺(106g，2eq)和过氧化芐基(0.7g，0.01eq)溶于四氯化碳(430ml)，将混合物加热至85℃，以HPLC监测反应，待反应完成后，过滤移除沉淀物并以甲醇洗，接着再结晶纯化，纯化后的产物浓缩至干燥后得白色固体产物(123g，92.3％)。FD-MS分析C15H9Br3O：理论值444.94，实际值444.94。
步骤2：中间物B1-2的合成
取中间物B1-1(116.0g，1.0eq)溶于呋喃/四氢呋喃(体积比2/1，960ml)，将反应冷却至0℃后加入仲丁基氧化钾(KO-t-Bu，87.8g，3.0eq)，反应于0℃下搅拌1小时再回温至室温搅拌12小时，待反应完成后，以去离子水终止反应，有机层以溶剂萃取回复并以硫酸钠干燥，从有机层中以减压蒸馏移除溶剂，并将生成的残余物以硅胶管柱层析法纯化，纯化后的产物浓缩干燥，得浅黄色固体产物(46.8g，51.1％)。FD-MS分析C19H11BrO2：理论值351.19，实际值351.19。
步骤3：中间物B1-3的合成
取中间物B1-2(53.5g，1.0eq)和5％Pd/C(8.1g，0.025eq)于乙酸乙酯(535ml)形成一悬浮液，反应在氢气下搅拌3-6小时，生成的混合物以硅藻土过滤并以乙酸乙酯洗，减压浓缩滤液后得黄色固体中间物B1-3(100g，100％)，中间物B1-3不经过进一步纯化直接用于下一步反应。
步骤4：中间物B1的合成
取中间物B1-3(53g，1.0eq)和对甲苯磺酸(57g，2.0eq)于甲苯(530ml)下加热回流12小时，将混合物冷却至室温后以饱和碳酸氢钠水溶液终止反应，再以二氯甲烷萃取，有机层依序以水、食盐水洗后，以无水硫酸钠干燥，减压浓缩生成的溶液并以硅胶管柱层析法纯化，使用二氯甲烷/己烷(体积比1/1)作为冲提液，得浅黄色固体中间物B1(46.0g，91.5％)。FD-MS分析C19H11BrO：理论值335.19，实际值335.19。
中间物B2-B4的合成
除了将制备中间物B1的3-溴二苯并[a,d]环庚-5-酮以制备中间物B2的2-溴二苯并[a,d]环庚-5-酮取代，或以制备中间物B3的3,7-二溴二苯并[a,d]环庚-5-酮取代，或以制备中间物B4的二苯并[a,d]环庚-5-酮取代外，中间物B2-B4的合成步骤与制备中间物B1的方法相同，所有步骤的中间物、产率和质谱分析数据列于下表4中。
表4
合成实施例3–中间物C1-C4及其合成
用于制备化学式(I)的化合物的中间物C1-C4列于以下表5中，其中，每个中间物下方的数字表示其CAS编号。
表5–中间物C1-C4
中间物C4的合成
取1-溴-2-氯-4-碘化苯(1.0eq)、4-氯苯基硼酸(1.1eq)、乙酸钯(0.95g，0.01eq)、三苯基膦(4.45g，0.04eq)和3.0M碳酸钾水溶液(5.86g，2.0eq溶于144mL H2O)溶于甲苯(730mL)中，反应在氮气下加热至65℃反应12小时，将反应冷却至室温，以旋转蒸发器移除溶剂，残余物以管柱层析法纯化，得中间物C4(65％)。MS:[M]+＝301.99。
合成实施例4–中间物D1-D13及其合成
用于制备化学式(I)的化合物的中间物D1-D15列于以下表6中。
表6–中间物D1-D15
中间物D1的合成
[流程III]
中间物D1可根据以上流程III来制备。
步骤1：螺环醇的合成
取中间物C1(1.0eq)溶于无水四氢呋喃(0.4M)在-78℃下搅拌，逐滴加入正丁基锂(1.0eq)搅拌20分钟后，加入中间物B4(0.7eq)并将反应回温至室温，以HPLC监测反应，待反应完成后，以水终止反应并将水层以乙酸乙酯萃取，合并萃取溶液与有机层以饱和食盐水洗，再以硫酸镁干燥，待干燥后将混合物抽吸过滤并浓缩滤液，得到浅黄色螺环醇的粉状固体(65g)，不须进一步纯化直接用于步骤2。
步骤2：中间物D1的合成
于螺环醇(1eq)中，加入乙酸(w/v＝1/3的反应物)及硫酸(5滴)，在110℃下搅拌混合物6小时，以HPLC监测反应，待反应完成后以过滤分离沉淀物，以管柱层析法纯化剩余的物质，得白色固体中间物D1(58g，91.0％)。FD-MS分析C31H19Br：理论值471.39，实际值471.39。
中间物D2-D13的合成
除了将制备中间物D1的中间物B4和中间物C1以下表7的化合物取代，中间物D2-D13的合成步骤与制备中间物D1的方法相同，所得的中间物D2-D12为白色固体，此外，中间物D1-D13的产率和质谱分析数据列于下表7中。
表7
中间物D14和D15的合成
[流程IV]
中间物D14和D15可根据以上流程IV来制备。
取中间物D1或D5(1.0eq)、硼酸(1.1eq)、乙酸钯(0.01eq)、三苯基膦(0.04eq)和碳酸钾(1.5eq，3.0M)溶于甲苯，将反应加热至100℃反应12小时，待反应完成后，在真空下移除挥发物，将剩余溶液以二氯甲烷萃取(3×60mL)，合并有机萃取物以食盐水溶液洗，硫酸钠干燥并浓缩留下黄色固体，进一步将粗产物以硅胶管柱层析法纯化，此外，中间物D14和D15的产率和质谱分析数据列于下表8中。
表8
合成实施例5–化合物(1)-(30)
化合物(1)-(26)的合成
本发明的化合物可根据以下流程V来合成。
[流程V]
简要地，取中间物D1-D15(1.0eq)、中间物A1-A9(1.05eq)、乙酸钯(0.005eq)、四氟硼酸三叔丁基磷(P(t-Bu)3HBF4，0.02eq)和第三丁基氧化钠(1.5eq)溶于甲苯(0.3M)，将反应加热至90℃反应8-24小时，待完成反应后，在真空下移除挥发物，剩余溶液以二氯甲烷萃取(3×60mL)，合并有机萃取物以食盐水溶液洗，硫酸钠干燥并浓缩留下黄色固体，进一步将粗产物以硅胶管柱层析法纯化，得白色固体的最终产物。
化合物(27)的合成
取中间物A9(1.0eq)、中间物D3(2.1eq)、乙酸钯(0.01eq)、四氟硼酸三叔丁基磷(P(t-Bu)3HBF4，0.04eq)和第三丁基氧化钠(3.0eq)溶于甲苯(0.3M)，将反应加热至90℃反应24小时，待完成反应后，在真空下移除挥发物，剩余溶液以二氯甲烷萃取(3×60mL)，合并有机萃取物以食盐水溶液洗，硫酸钠干燥并浓缩留下黄色固体，进一步将粗产物以硅胶管柱层析法纯化，得白色固体的最终产物。
产物(1)-(30)所使用的中间物、产率及质谱分析数据列于下表9中。
表9
实施例–OLED装置制造
将一具有厚度为的ITO(氧化铟锡)涂层的玻璃基板放置于包含清洗剂的蒸馏水中，以超声波洗涤，在此，该清洗剂是由Fischer Co.所制造，且蒸馏水是经过过滤器(Millipore Co.)二次过滤而得。ITO以清洁剂经过30分钟清洗后，以蒸馏水进行2次超声波清洗共10分钟，接着以异丙醇、丙酮和甲醇溶剂超声波清洗并干燥，再将其转移到等离子体清洁器(plasma cleaner)，接着以氧等离子体将该基板清洁5分钟，并将其转移至真空蒸发器。
各种有机材料和金属材料依序沉积于ITO基板上而获得本实施例的OLED装置，在沉积期间，真空程度维持在1×10-6至3×10-7torr。此外，下述OLED装置所使用的材料的化学式及代号，列于下表10中。
制备蓝色OLED装置
在制备本实施例的蓝色OLED装置时，首先将HAT沉积在ITO基板上，而得厚度为的第一空穴注入层。再将掺杂有HAT(5.0wt％)的HI-2沉积于第一空穴注入层上，而得到厚度为的第二空穴注入层。
接着，沉积HT-1或本发明化合物而得到第一空穴传输层(HT1)，厚度为和/或沉积HT-2或本发明化合物而得到第二空穴传输层(HT2)，厚度为
而后，将掺杂有BD(3.5wt％)的BH沉积在第一或第二空穴传输层上，而得到厚度为的发光层。将掺杂有Liq(35.0wt％)的ET沉积在发光层上，而得到厚度为的电子传输层。将Liq沉积于电子传输层上，得到厚度为的电子注入层。将Al沉积在电子注入层上，而得到厚度为的阴极。
经由前述步骤，可得到下述测试例所使用的蓝色OLED装置。
制备绿色OLED装置
绿色OLED装置的制备与蓝色OLED装置的制备相似，除了第二空穴注入层、发光层及电子传输层不同外。
在此，第二空穴注入层厚度为将掺杂有GD(10wt％)的GH沉积在空穴传输层上，而得到厚度为的发光层。电子传输层厚度为
制备红色OLED装置
红色OLED装置的制备与蓝色OLED装置的制备相似，除了第二空穴注入层、发光层及电子传输层不同外。
在此，第二空穴注入层厚度为将掺杂有RD(3.5wt％)的RH沉积在空穴传输层上，而得到厚度为的发光层。电子传输层厚度为
表10
OLED装置测量
以PR-650测量所制得的蓝色、绿色和红色OLED装置的装置性能。以1000尼特(nit)收集蓝色和红色OLED装置数据，以3000尼特(nit)收集绿色OLED装置数据。数据如CIE、发光效率(Eff.)和驱动电压(Voltage)列于下表11-13中。
表11
表12
表13
根据表11-13的结果，使用化学式(I)所示的化合物的OLED装置具有提升的发光效率以及低驱动电压，因此，本发明的化学式(I)所示的化合物可以有效地用来作为OLED装置的空穴传递材料。
以上所述的具体实施例，对本发明的目的、技术方案和有益效果进行了进一步详细说明，应理解的是，以上所述仅为本发明的具体实施例而已，并不用于限制本发明，凡在本发明的精神和原则之内，所做的任何修改、等同替换、改进等，均应包含在本发明的保护范围之内。

Claims (24)

1.一种如化学式(I)所示的化合物：
其中，Ar1、Ar2、Ar3和Ar4各自独立为氢、氘、经取代或未经取代C1-C20的烷基、经取代或未经取代C6-C40的芳基、经取代或未经取代C1-C40的杂环基、或经取代或未经取代的胺基；或Ar1和Ar2与其所键结的N原子一起形成经取代或未经取代C1-C40的杂环基；或Ar3和Ar4与其所键结的N原子一起形成经取代或未经取代C1-C40的杂环基；
L和Q各自独立为经取代或未经取代C6-C40的亚芳基；
G为氘、经取代或未经取代C1-C20的烷基、经取代或未经取代C6-C40的芳基、经取代或未经取代C1-C40的杂环基、或-NR1R2；
R1和R2各自独立为氢、氘、经取代或未经取代C1-C20的烷基、经取代或未经取代C6-C40的芳基、或经取代或未经取代C1-C40的杂环基；
n1和n2各自独立为0或1；
m1和m2各自独立为0、1或2，且m1和m2不同时为0；以及
q为0、1或2。
2.如权利要求1所述的化合物，其中，Ar1、Ar2、Ar3和Ar4各自独立为经取代或未经取代C6-C40的芳基、或经取代或未经取代C1-C40的杂环基；或Ar1和Ar2与其所键结的N原子一起形成经取代或未经取代C1-C40的杂环基；或Ar3和Ar4与其所键结的N原子一起形成经取代或未经取代C1-C40的杂环基。
3.请权利要求2所述的化合物，其中，Ar1、Ar2、Ar3和Ar4各自独立为经取代或未经取代C6-C40的芳基、或经取代或未经取代C1-C40的杂芳基；或Ar1和Ar2与其所键结的N原子一起形成经取代或未经取代C1-C40的杂芳基；或Ar3和Ar4与其所键结的N原子一起形成经取代或未经取代C1-C40的杂芳基。
4.如权利要求1所述的化合物，其中，Ar1、Ar2、Ar3和Ar4各自独立为经取代或未经取代的苯基、经取代或未经取代的联苯基、经取代或未经取代的联三苯基、经取代或未经取代的茀基、经取代或未经取代的三苄基氧杂环庚烯基、经取代或未经取代的二苯并呋喃基、经取代或未经取代的二苯并噻吩基、经取代或未经取代的萘基、或经取代或未经取代的三苄基-氮呯基。
5.如权利要求4所述的化合物，其中，Ar1、Ar2、Ar3和Ar4各自独立为未经取代的苯基、经烷基取代的苯基、未经取代的联苯基、未经取代的联三苯基、未经取代的茀基、经烷基取代的茀基、未经取代的三苄基氧杂环庚烯基、未经取代的二苯并呋喃基、或未经取代的萘基。
6.如权利要求1所述的化合物，其中，m1为1；且m2为0或1。
7.如权利要求1所述的化合物，其中，m1为1；m2为0；且Ar1和Ar2与其所键结的N原子一起形成经取代或未经取代C1-C40的杂芳基。
8.如权利要求7所述的化合物，其中，Ar1和Ar2与其所键结的N原子一起形成未经取代的三苄基-氮呯基。
9.如权利要求1所述的化合物，其中，L和Q各自独立为经取代或未经取代的亚苯基、亚联苯基或亚萘基。
10.如权利要求9所述的化合物，其中，L和Q各自独立为未经取代的亚苯基。
11.如权利要求1所述的化合物，其中，q为0或1。
12.如权利要求1所述的化合物，其中，q为1；且G为经取代或未经取代C6-C40的芳基、经取代或未经取代C1-C40的杂环基、或-NR1R2，其中R1和R2各自独立为经取代或未经取代C6-C40的芳基。
13.如权利要求12所述的化合物，其中，G为包含一氮原子的经取代或未经取代C1-C40的杂芳基或-NR1R2，其中R1和R2为相同的经取代或未经取代的苯基、联苯基或亚萘基。
14.如权利要求13所述的化合物，其中，G为未经取代的吡啶基或-NR1R2，其中R1和R2为未经取代的苯基。
15.如权利要求1所述的化合物，其中，该化合物为以下化学式(I-1)至(I-18)中的任一所表示：
其中，Ar1、Ar2、Ar3、Ar4、L、Q、G、n1、n2与化学式(I)所示相同。
16.如权利要求1所述的化合物，其中–Ln1-NAr1Ar2及–Qn2-NAr3Ar4各自独立选自由下列所组成的群组：
其中，*代表键结位置；
Ra及Rb各自独立为C1-20烷基；以及
x及y各自独立为1或2。
17.如权利要求16所述的化合物，其中n1或n2为0。
18.如权利要求1所述的化合物，其中n1或n2为1，–Ln1-NAr1Ar2及–Qn2-NAr3Ar4各自独立选自由下列所组成的群组：
其中，*代表键结位置；
Ra及Rb各自独立为C1-20烷基；以及
x及y各自独立为1或2。
19.如权利要求1所述的化合物，其中该化合物为下列化合物(1)至(224)任一所表示：
20.一种有机电子装置，包含：
一第一电极；
一第二电极；以及
一有机层，设置于该第一电极与该第二电极间，其中该有机层包含如权利要求1所述的化合物。
21.如权利要求20所述的有机电子装置，其中，该有机电子装置为一有机发光装置。
22.如权利要求21所述的有机电子装置，其中，该有机层包含一空穴传输层；且该空穴传输层包含如权利要求1所述的化合物。
23.如权利要求21所述的有机电子装置，其中，该有机层包含一空穴注入层；且该空穴注入层包含如权利要求1所述的化合物。
24.如权利要求21所述的有机电子装置，其中，该有机层包含一电子阻隔层；且该电子阻隔层包含如权利要求1所述的化合物。
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