CN113801066B - 咪唑衍生物及其应用 - Google Patents
咪唑衍生物及其应用 Download PDFInfo
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- CN113801066B CN113801066B CN202010864440.7A CN202010864440A CN113801066B CN 113801066 B CN113801066 B CN 113801066B CN 202010864440 A CN202010864440 A CN 202010864440A CN 113801066 B CN113801066 B CN 113801066B
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Abstract
Description
技术领域
本发明涉及有机电致发光材料技术领域,具体涉及一种咪唑衍生物及其应用。
背景技术
一般而言,有机发光现象是指在对有机物质施加电能时发出光的现象。即在阳极与阴极之间配置有机层时,如果在两个电极之间施加电压,则空穴会从阳极注入至有机层,电子会从阴极注入至有机层。当所注入的空穴和电子相遇时,会形成激子,当该激子跃迁至基态时,会发出光和热。
作为有效制造有机电致发光元件的一种方法,一直以来进行了以多层结构来代替单层制造元件内的有机层的研究,1987年唐提出了空穴层和发光层的功能层的层叠结构的有机电致发光元件,目前使用的大部分的有机电致发光元件包括:基板、阳极、从阳极接收空穴的空穴注入层、传输空穴的空穴传输层、空穴与电子进行再结合而发出光的发光层、传输电子的电子传输层、从阴极接收电子的电子注入层和阴极。这样以多层制作有机电致发光元件的理由是,由于空穴与电子的移动速度不同,因此如果制造适当的空穴注入层和传输层、电子传输层和电子注入层,则能够有效传输空穴和电子,元件内实现空穴与电子的均衡,能够提高激子利用率。
作为与电子传输材料有关的最早报告,可以举出二唑衍生物。之后报告了***衍生物和菲咯啉衍生物表现出电子传输性。可应用于电子传输层的物质作为有机单分子物质,报告了对于电子稳定性和电子移动速度相对优异的有机金属络合物为良好的候选物质,稳定性优异且电子亲和度大的Liq为最优异的物质,目前也是最基本使用的物质。
此外,作为以往的可应用于电子注入层和传输层的物质,报告了很多具有咪唑基、唑基、噻唑基、螺芴基的有机单分子物质。例如,中国专利局公开授权的CN103833507B、CN107573328B、CN107556310B以及由柯达公司于1996年发表的美国专利US5,645,948中记载的TPBI为具有咪唑基的电子传输层用物质,其结构中,在苯的1,3,5取代位置上含有三个N-苯基苯并咪唑基,就功能而言,不仅具有传输电子的能力,而且具有阻断从发光层跨越来的空穴的功能,但在实际应用在元件时存在热稳定性低、驱动电压偏高的问题。
由此,为了克服如上所述的以往技术问题而进一步提高有机电致发光元件的特性,继续要求对于在有机电致发光元件中可用作电子注入和传输用物质的更加稳定且有效的物质的开发。
发明内容
本发明的目的是提供一种咪唑衍生物。
本发明另一个目的是提供一种含有上述咪唑衍生物的有机电致发光材料。
本发明还有一个目的是提供一种有机电致发光器件,以及上述咪唑衍生物在制备有机电致发光器件中的应用。
为实现上述目的,本发明采用如下技术方案:
一种咪唑衍生物,其结构式如式I所示:
式中:
R1、R2各自独立地选自一个或多个相同或不同的氢、氘、卤素、取代或未取代的C6-C60芳香基、取代或未取代的C6-C60芳香乙烯基、取代或未取代的C6-C60稠环芳香基、取代或未取代的C6-C60芳胺基、或者取代或未取代的C2-C60杂环芳基;
Ar1为单键、取代或未取代的C6-C60的亚芳基、或者取代或未取代的C2-C60的亚杂芳基;
Ar2、Ar3、Ar4各自独立地选自取代或未取代的C6-C60芳香基、取代或未取代的C6-C60稠环芳香基、或者取代或未取代的C2-C60杂环芳基,其中Ar4除上述基团以外还可以是氢、氘、氟或腈基;
其中两个或多个相邻的R1、R2、Ar1、Ar2、Ar3或Ar4可任选地形成另外的一个或多个取代或未取代的环,在所形成的环中含有或不含有一个或多个杂原子N、P、B、O或S;
n表示1-5的整数;
X为C或N。
本说明书中,相邻基团彼此结合而形成的取代或未取代的环中,“环”是指取代或未取代的烃环、或者取代或未取代的杂环。
优选地,上述咪唑衍生物中,所述R1、R2、Ar2、Ar3、Ar4基团中的任意一个或多个所述C2-C60杂环芳基的环结构中独立地含有一个或多个杂原子N、O或S。
优选地,上述咪唑衍生物中,所述R1、R2、Ar2、Ar3、Ar4基团中的任意一个或多个所述取代或未取代的C2-C60杂环芳基独立地选自以下II-1~II-17所示基团中的一种或多种:
其中,
Z1、Z2、Z3各自独立地选自氢、氘、卤素、羟基、腈基、硝基、氨基、脒基、肼基、腙基、羧基或其羧酸盐、磺酸基或其磺酸盐、磷酸基或其磷酸盐、C1-C60烷基、C2-C60烯基、C2-C60炔基、C1-C60烷氧基、C3-C60环烷烃基、C3-C60环烯烃基、C6-C60芳基、至少含有一个-F、-CN或C1-C10烷基的C6-C60芳基、取代或未取代的C6-C60芳氧基、取代或未取代的C6-C60芳硫醚基、或者取代或未取代的C2-C60杂环芳基;
x1表示1-4的整数;x2表示1-3的整数;x3表示1或2;x4表示1-6的整数;x5表示1-5的整数;
T1表示氧原子或硫原子;
优选地,上述咪唑衍生物中,所述Ar1选自以下III-1~III-15所示基团中的任意一种或多种:
其中,
Z11和Z12各自独立地选自氢、氘氢、卤原子、羟基、腈基、硝基、氨基、脒基、肼基、腙基、羧基或其羧酸盐、磺酸基或其磺酸盐、磷酸基或其磷酸盐、C1-C60烷基、C2-C60烯基、C2-C60炔基、C1-C60烷氧基、C3-C60环烷烃基、C3-C60环烯烃基、C6-C60芳基、至少含有一个-F、-CN或C1-C10烷基的C6-C60芳基、取代或未取代的C6-C60芳氧基、取代或未取代的C6-C60芳硫醚基、或者取代或未取代的C2-C60杂环芳基;
Z13表示取代或未取代的C6-C60芳基、取代或未取代的C6-C60芳氧基、取代或未取代的C6-C60芳硫醚基、或者取代或未取代的C2-C60杂环芳基;
y1表示1-4的整数;y2表示1-6的整数;y3表示1-3的整数;y4表示1-5的整数;
T2表示氧原子或硫原子;
本说明书中,“取代或未取代的”这一用语是指,被选自氢、氘、卤原子、羟基、腈基、硝基、氨基、脒基、肼基、腙基、羧基或其羧酸盐、磺酸基或其磺酸盐、磷酸基或其磷酸盐、C1-C60烷基、C2-C60烯基、C2-C60炔基、C1-C60烷氧基、C3-C60环烷基、C3-C60环烯基、C6-C60芳基、C6-C60芳氧基、C6-C60芳硫醚基和C2-C60杂环芳基中的1个以上的取代基取代或未取代,或者被上述例示的取代基中的2个以上的取代基连接而成的取代基取代或未取代。
优选地,所述咪唑衍生物的结构式为以下CJH-P01至CJH-P136任意一种:
本发明还提供一种材料,所述材料的原料包含上述的咪唑衍生物有机电致发光材料,优选的,所述材料为有机电致发光材料。包含本发明的咪唑衍生物的材料具有载流子传输的能力。
本发明还提供一种有机电致发光器件,其包含第一电极、第二电极和置于所述第一电极、所述第二电极之间的一层以上的有机层;所述有机层中的至少一层的材料包含上述的咪唑衍生物。
所述有机电致发光器件包含阴极、阳极和至少一个发光层。除了这些层之外,它还可以包含其它的层,例如在每种情况下,包含一个或多个空穴注入层、空穴传输层、空穴阻挡层、电子传输层、电子注入层、激子阻挡层、电子阻挡层和/或电荷产生层。具有例如激子阻挡功能的中间层同样可引入两个发光层之间。然而,应当指出,这些层中的每个并非必须都存在。此处所述有机电致发光装置可包含一个发光层,或者它可包含多个发光层。即,将能够发光的多种发光化合物用于所述发光层中。特别优选具有三个发光层的体系,其中所述三个层可显示蓝色、绿色和红色发光。如果存在多于一个的发光层,则根据本发明,这些层中的至少一个层包含本发明的化合物。
进一步地,根据本发明的有机电致发光器件不包含单独的空穴注入层和/或空穴传输层和/或空穴阻挡层和/或电子传输层,即发光层与空穴注入层或阳极直接相邻,和/或发光层与电子传输层或电子注入层或阴极直接相邻。
在根据本发明的有机电致发光器件的其它层中,特别是在空穴注入和空穴传输层中以及在电子注入和电子传输层中,所有材料可以按照根据现有技术通常所使用的方式来使用。本领域普通技术人员因此将能够在不付出创造性劳动的情况下与根据本发明的发光层组合使用关于有机电致发光元件所知的所有材料。
此外优选如下的有机电致发光装置,其特征在于借助于升华方法施加一个或多个层,其中在真空升华装置中在低于10-5Pa、优选低于10-6Pa的初压下通过气相沉积来施加所述材料。然而,所述初压还可能甚至更低,例如低于10-7Pa。
同样优选如下的有机电致发光器件,其特征在于借助于有机气相沉积方法或借助于载气升华来施加一个或多个层,其中,在10-5Pa至1Pa之间的压力下施加所述材料。该方法的特别的例子是有机蒸气喷印方法,其中所述材料通过喷嘴直接施加,并且因此是结构化的。
此外优选如下的有机电致发光器件,从溶液中,例如通过旋涂,或借助于任何所希望的印刷方法例如丝网印刷、柔性版印刷、平版印刷、光引发热成像、热转印、喷墨印刷或喷嘴印刷,来产生一个或多个层。可溶性化合物,例如通过适当的取代获得可溶性化合物。这些方法也特别适于低聚物、树枝状大分子和聚合物。此外可行的是混合方法,其中例如从溶液中施加一个或多个层并且通过气相沉积施加一个或多个另外的层。
这些方法是本领域普通技术人员通常已知的,并且他们可以在不付出创造性劳动的情况下将其应用于包含根据本发明的化合物的有机电致发光器件。
因此,本发明还涉及制造根据本发明的有机电致发光器件的方法,其特征在于借助于升华方法来施加至少一个层,和/或特征在于借助于有机气相沉积方法或借助于载气升华来施加至少一个层,和/或特征在于从溶液中通过旋涂或借助于印刷方法来施加至少一个层。
此外,本发明涉及包含至少一种上文指出的本发明的咪唑衍生物。如上文关于有机电致发光器件指出的相同优选情况适用于所述本发明的咪唑衍生物。特别是,所述咪唑衍生物此外还可优选包含其它化合物。从液相处理根据本发明的咪唑衍生物,例如通过旋涂或通过印刷方法进行处理,需要根据本发明的化合物的制剂。这些制剂可以例如是溶液、分散体或乳液。出于这个目的,可优选使用两种或更多种溶剂的混合物。合适并且优选的溶剂例如是甲苯,苯甲醚,邻二甲苯、间二甲苯或对二甲苯,苯甲酸甲酯,均三甲苯,萘满,邻二甲氧基苯,四氢呋喃,甲基四氢呋喃,四氢吡喃,氯苯,二噁烷,苯氧基甲苯,特别是3-苯氧基甲苯,(-)-葑酮,1,2,3,5-四甲基苯,1,2,4,5-四甲基苯,1-甲基萘,2-甲基苯并噻唑,2-苯氧基乙醇,2-吡咯烷酮,3-甲基苯甲醚,4-甲基苯甲醚,3,4-二甲基苯甲醚,3,5-二甲基苯甲醚,苯乙酮,α-萜品醇,苯并噻唑,苯甲酸丁酯,异丙苯,环己醇,环己酮,环己基苯,十氢化萘,十二烷基苯,苯甲酸乙酯,茚满,苯甲酸甲酯,1-甲基吡咯烷酮,对甲基异丙基苯,苯***,1,4-二异丙基苯,二苄醚,二乙二醇丁基甲基醚,三乙二醇丁基甲基醚,二乙二醇二丁基醚,三乙二醇二甲基醚,二乙二醇单丁基醚,三丙二醇二甲基醚,四乙二醇二甲基醚,2-异丙基萘,戊苯,己苯,庚苯,辛苯,1,1-双(3,4-二甲基苯基)乙烷,或这些溶剂的混合物。
优选地,上述有机电致发光器件中,所述有机层包括空穴注入层、空穴传输层、空穴阻挡层、发光层、光折射层、电子传输层、电子注入层或电子阻挡层。
本发明还提供上述的咪唑衍生物在制备有机电致发光器件中的应用。
另外,如无特殊说明,本发明中所用原料均可通过市售商购获得,本发明所记载的任何范围包括端值以及端值之间的任何数值以及端值或者端值之间的任意数值所构成的任意子范围。
本发明所取得的有益效果:
本发明提供的式I所示咪唑衍生物,增大了咪唑环的π-π共轭强度,提高了材料热稳定性和输送电子的能力,利用本发明的材料制备的有机电致发光器件可显著降低启动电压、提高发光效率和亮度。
附图说明
图1是本发明实施例12的底发光有机电致发光器件的结构示意图,其中,1-基板,2-阳极层,3-空穴注入层,4-空穴传输层,5-有机发光层,6-电子传输层,7-电子注入层,8-阴极层。
图2是本发明实施例13的顶发光有机电致发光器件的结构示意图,其中,1-基板,2-阳极层,3-空穴注入层,4-电子阻挡层,5-有机发光层,6-空穴阻挡层,7-电子注入层,8-阴极层。
具体实施方式
以下结合具体实施例对本发明作进一步详细说明,但不用来限制本发明的范围。
在本发明的描述中,除非另有说明,“多个”的含义是两个或两个以上;术语“上”、“下”等指示的方位或位置关系为基于附图所示的方位或位置关系,仅是为了便于描述本发明和简化描述,而不是指示或暗示所指的装置或元件必须具有特定的方位、以特定的方位构造和操作,因此不能理解为对本发明的限制。
以下实施例中所使用的实验方法如无特殊说明,均为常规方法。以下实施例中所用的实验原料和相关设备等,如无特殊说明,均可从商业途径得到,所述百分比如无特殊说明,均为质量百分比。
下述实施例对OLED材料及器件进行性能测试的测试仪器及方法如下:
OLED器件性能检测条件:
亮度和色度坐标:使用光谱扫描仪PhotoResearch PR-715测试;
电流密度和起亮电压:使用数字源表Keithley 2420测试;
功率效率:使用NEWPORT 1931-C测试。
实施例1
化合物CJH-P55的制备方法,包括如下步骤:
第一步:中间体Int-1的制备
54.5mmol的N-苯基苯甲脒SM-1和54.5mmol的查尔酮、1.5g的无水氯化铁,再加入1.2g的碘,加入80ml的二氯苯,通入氧气,升温至110℃搅拌反应8小时,冷却到室温,过滤,滤饼用石油醚洗,再用乙醇重结晶,得黄色固体Int-1,收率81%。
第二步:中间体Int-2的制备
109.4mmol的甲氧基甲基三苯基氯化磷分散在500mL无水四氢呋喃中,在氮气保护下,用液氮降温至-78℃,分批加入12.3g(109.4mmol)的叔丁醇钾,升至室温搅拌反应30分钟后,再次降温至-78℃,滴加入91.2mmol的原料Int-1溶于四氢呋喃的溶液,加完后,保温搅拌反应1小时,升到室温搅拌反应过夜,加入150mL饱和氯化铵水溶液,用乙酸乙酯萃取,有机相干燥,过滤,减压浓缩干,用硅胶柱分离纯化,得到黄色固体,收率:65%。
第三步:中间体Int-3的制备
20.0mmol的中间体Int-2溶解于160mL的丙酮和40mL的水中,加入25mL的48%氢溴酸水溶液,搅拌反应24小时,用乙酸乙酯萃取,有机相干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,再用乙醇重结晶,得黄色固体Int-3,收率94%。
第四步:中间体Int-4的制备
18.0mmol的中间体Int-3溶解于80mL的乙腈中,加入2.7mmol的N-羟基邻苯二甲酰亚胺,通入氧气,升温至80℃搅拌反应24小时,冷却到室温,减压浓缩干,用硅胶柱分离纯化,得褐色固体Int-4,收率92%。
第五步:中间体Int-5的制备
15.0mmol的中间体Int-4溶解于100mL的二氯甲烷中,加入15.0mL的三氟甲磺酸,升温回流搅拌反应24小时,冷却到室温,减压浓缩干,加入冰水搅拌1小时,过滤,滤饼用水洗,用硅胶柱分离纯化,再用乙醇重结晶,得黄色固体Int-5,收率77%。
第六步:化合物CJH-P55的制备
12.0mmol的2-氯-4,6-二苯基-1,3,5-三嗪溶解于80mL干燥的四氢呋喃中,在氮气保护下,用液氮降温至-78℃,滴加入4.8mL的2.5M丁基锂正己烷溶液,搅拌反应1小时,滴加入10.0mmol的中间体Int-5溶于干燥四氢呋喃的溶液,升到室温搅拌反应1小时,滴加入20mL的浓盐酸,搅拌反应1小时,用乙酸乙酯萃取,收集有机相,干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,再用二氯甲烷/乙醇重结晶,得到产物CJH-P55,收率92%。MS(MALDI-TOF):m/z 628.2519[M+H]+;1HNMR(δ、CDCl3):8.82(1H,s);8.34~8.31(4H,m);8.11~8.09(1H,m);7.98~7.91(4H,m);7.85~7.78(2H,m);7.68~7.56(3H,m);7.49~7.24(14H,m)。
实施例2
参照实施例1的合成方法,制备下列化合物,即方法步骤同实施例1,不同之处仅在于根据所需产物不同,根据实际需要采用不同的化合物替换实施例1第一步中的N-苯基苯甲脒,替换实施例1第四步中的2-氯-4,6-二苯基-1,3,5-三嗪,并根据摩尔量更改该化合物的质量用量,制备编号CJH-P24、CJH-P25、CJH-P27、CJH-P40~CJH-P42、CJH-P46、CJH-P48、CJH-P53、CJH-P54、CJH-P56~CJH-P61、CJH-P113、CJH-P116~CJH-P118的化合物。
实施例3
化合物CJH-P03的制备,包括如下步骤:
第一步:中间体Int-6的制备
合成操作参照实施例1的第一步,将实施例1第一步的SM-1替换为SM-3,制备得到中间体Int-6,黄色固体,收率88%。
第二步:中间体Int-7的制备
合成操作参照实施例1的第二步,将实施例1第二步的中间体Int-1替换为中间体Int-6,制备得到中间体Int-7,黄色固体,收率62%。
第三步:中间体Int-8的制备
合成操作参照实施例1的第三步,将实施例1第三步的中间体Int-2替换为中间体Int-7,制备得到中间体Int-8,黄色固体,收率97%。
第四步:中间体Int-9的制备
合成操作参照实施例1的第四步,将实施例1第四步的中间体Int-3替换为中间体Int-8,制备得到中间体Int-9,黄色固体,收率90%。
第五步:中间体Int-10的制备
合成操作参照实施例1的第五步,将实施例1第五步的中间体Int-4替换为中间体Int-9,制备得到中间体Int-10,黄色固体,收率82%。
第六步:中间体Int-11的制备
合成操作参照实施例1的第六步,将实施例1第六步的中间体Int-5替换为中间体Int-10,制备得到中间体Int-11,黄色固体,收率87%。
第七步:化合物CJH-P03的制备
9.5mmol的(4-(4,6-二苯基-1,3,5-三嗪-2-基)苯基)硼酸、8.6mmol的Int-11、3.7g(34.9mmol)的碳酸钠和5mg的Pd(PPh3)4催化剂,加入40mL的甲苯和10mL的乙醇以及5mL的水,升温回流搅拌反应12小时,冷却到室温,用乙酸乙酯萃取,有机相干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,再用乙醇加热至沸腾,趁热过滤,得4.9g的产物CJH-P03,收率73%。MS(MALDI-TOF):m/z 781.3097[M+H]+;1HNMR(δ、CDCl3):9.11(1H,s);8.81~8.78(4H,m);8.61~8.59(1H,m);8.39~8.27(4H,m);8.06~7.87(10H,m);7.78~7.74(2H,m);7.69~7.61(7H,m);7.42~7.27(7H,m)。
实施例4
参照实施例3的合成方法,制备下列化合物,即方法步骤同实施例3,不同之处仅在于根据所需产物不同,根据实际需要采用不同的化合物替换实施例3第一步中的N-苯基苯甲脒,替换实施例3第七步中的(4-(4,6-二苯基-1,3,5-三嗪-2-基)苯基)硼酸,并根据摩尔量更改该化合物的质量用量,制备编号CJH-P01、CJH-P02、CJH-P04~CJH-P23、CJH-P26、CJH-P28~CJH-P31、CJH-P33~CJH-P39、CJH-P43~CJH-P45、CJH-P47、CJH-P49~CJH-P52、CJH-P62~CJH-P112、CJH-P114、CJH-P115、CJH-P119、CJH-P120的化合物。
实施例5
化合物CJH-P32的制备,包括如下步骤:
第一步:中间体Int-12的制备
合成操作参照实施例1的第六步,将实施例1第六步的中间体Int-5替换为中间体Int-10,制备得到中间体Int-12,黄色固体,收率85%。
第二步:中间体Int-13的制备
15.0mmol的中间体Int-12溶解于80mL干燥的四氢呋喃中,在氮气保护下,用液氮降温至-78℃,滴加入7.2mL的2.5M丁基锂正己烷溶液,搅拌反应1小时,滴加入18.0mmol的二苯基氯化磷溶于干燥四氢呋喃的溶液,升到室温搅拌反应1小时,滴加入20mL的饱和氯化铵水溶液,搅拌反应1小时,用乙酸乙酯萃取,收集有机相,干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得白色固体Int-13,收率82%。
第三步:化合物CJH-P32的制备
10.0mmol的中间体Int-13溶解于60mL的二氯甲烷中,加入5mL的35%双氧水,升温回流搅拌反应12小时,冷却到室温,用水洗、有机相再用饱和亚硫酸氢钠水溶液洗、水洗,有机相干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,再用乙酸乙酯加热至沸腾,趁热过滤,得产物CJH-P32,收率93%。MS(MALDI-TOF):m/z 828.2906[M+H]+;1HNMR(δ、CDCl3):8.81~8.78(4H,m);8.46~8.41(3H,m);8.09~8.07(2H,m);7.94~7.90(2H,m);7.76~7.65(9H,m);7.57~7.32(18H,m)。
实施例6
化合物CJH-P126的制备,包括如下步骤:
第一步:中间体Int-14的制备
在氮气保护下,向80mL的1,2-二氯乙烷中,加入122.0mg的无水三氯化铁和480.0mg的无水甲醇,于室温搅拌反应30分钟,加入15.0mmol实施例3第二步制备的中间体Int-7,升温至80℃搅拌反应8小时,减压浓缩干,用硅胶柱分离纯化,得到中间体Int-14,收率82%。
第二步:化合物CJH-P126的制备
10.0mmol的(4-(4,6-二苯基-1,3,5-三嗪-2-基)苯基)硼酸、8.3mmol的Int-14、3.5g(33.2mmol)的碳酸钠和5mg的Pd(PPh3)4催化剂,加入40mL的甲苯和10mL的乙醇以及5mL的水,升温回流搅拌反应12小时,冷却到室温,用乙酸乙酯萃取,有机相干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,再用乙醇加热至沸腾,趁热过滤,得到产物CJH-P126,收率76%。MS(MALDI-TOF):m/z704.2828[M+H]+;1HNMR(δ、CDCl3):8.80~8.78(4H,m);8.49~8.48(1H,m);8.38~8.35(2H,m);8.09~8.08(1H,m);7.91~7.72(10H,m);7.66~7.43(9H,m);7.35~7.22(6H,m)。
实施例7
参照实施例6的合成方法,制备下列化合物,即方法步骤同实施例6,不同之处仅在于根据所需产物不同,根据实际需要采用不同的化合物替换实施例3第一步中的查尔酮,替换实施例6第二步中的(4-(4,6-二苯基-1,3,5-三嗪-2-基)苯基)硼酸,并根据摩尔量更改该化合物的质量用量,制备编号CJH-P121~CJH-P125、CJH-P127~CJH-P130的化合物。
实施例8
化合物CJH-P132的制备,包括如下步骤:
第一步:中间体Int-15的制备
在氮气保护下,向80mL的二氯甲烷中,加入5mL的DAST(二乙胺基三氟化硫),用液氮降温至-40℃,加入15.0mmol实施例3第五步制备的中间体Int-10,搅拌反应2小时,滴加入20mL的饱和盐水,用二氯甲烷萃取,收集有机相,干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到中间体Int-15,收率96%。
第二步:化合物CJH-P132的制备
10.0mmol的中间体Int-15、12.0mmol的对腈基苯硼酸、3.7g(35.0mmol)的碳酸钠和58.0mg的Pd(PPh3)4催化剂,加入60mL的甲苯和30mL的乙醇以及20mL的水,升温回流搅拌反应12小时,冷却到室温,用乙酸乙酯萃取,有机相干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,再用二氯甲烷-乙醇重结晶,得到产物CJH-P132,收率83%。MS(MALDI-TOF):m/z516.1892[M+H]+;1HNMR(δ、CDCl3):8.12~8.10(2H,m);7.87~7.84(2H,m);7.78~7.74(3H,m);7.69~7.65(3H,m);7.60~7.53(6H,m);7.49~7.45(2H,m);7.41~7.32(3H,m);7.26~7.22(1H,m)。
实施例9
参照实施例8的合成方法,制备下列化合物,即方法步骤同实施例8,不同之处仅在于根据所需产物不同,根据实际需要采用不同的化合物替换实施例8第二步中的对腈基苯硼酸,并根据摩尔量更改该化合物的质量用量,制备编号CJH-P131、CJH-P133的化合物。
实施例10
化合物CJH-P136的制备,包括如下步骤:
第一步:中间体Int-16的制备
在氮气保护下,10.0mmol实施例3第五步制备的中间体Int-10溶解于60mL的二氯甲烷中,加入0.25mmol的碘化锌,用冰水浴降温至0℃,滴加入12.0mmol的三甲基硅氰,搅拌反应2小时,升到室温搅拌反应12小时,加入20mL的浓盐酸,于室温搅拌反应1小时,用二氯甲烷萃取,收集有机相,干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到中间体Int-16,收率95%。
第二步:化合物CJH-P136的制备
10.0mmol的中间体Int-16、12.0mmol的(4-(4,6-二苯基-1,3,5-三嗪-2-基)苯基)硼酸、3.7g(35.0mmol)的碳酸钠和58.0mg的Pd(PPh3)4催化剂,加入60mL的甲苯和30mL的乙醇以及20mL的水,升温回流搅拌反应12小时,冷却到室温,用乙酸乙酯萃取,有机相干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,再用二氯甲烷/甲醇重结晶,得到产物CJH-P136,收率85%。MS(MALDI-TOF):m/z 729.2784[M+H]+;1HNMR(δ、CDCl3):8.71~8.69(4H,m);8.47~8.44(2H,m);8.28~8.25(2H,m);8.08~8.06(2H,m);7.89~7.78(6H,m);7.71~7.66(4H,m);7.58~7.51(6H,m);7.46~7.36(6H,m)。
实施例11
参照实施例10的合成方法,制备下列化合物,即方法步骤同实施例10,不同之处仅在于根据所需产物不同,根据实际需要采用不同的化合物替换实施例10第二步中的(4-(4,6-二苯基-1,3,5-三嗪-2-基)苯基)硼酸,并根据摩尔量更改该化合物的质量用量,制备编号CJH-P134、CJH-P135的化合物。
实施例12
一种有机电致发光器件,为底发射光器件,其结构如图1所示,包括基板1、设于基板1上的阳极层2、设于阳极层2上的空穴注入层3、设于空穴注入层3上的空穴传输层4、设于空穴传输层4上的有机发光层5、设于有机发光层5上的电子传输层6、设于电子传输层6上的电子注入层7、设于电子注入层7上的阴极层8,其制备包括如下步骤:
1)将涂布了ITO导电层的玻璃基片在清洗剂中超声处理30分钟,在去离子水中冲洗,在丙酮/乙醇混合溶剂中超声30分钟,在洁净的环境下烘烤至完全干燥,用紫外光清洗机照射10分钟,并用低能阳离子束轰击表面。
实施例13
一种有机电致发光器件,为底发射光器件,其结构如图2所示,包括基板1、设于基板1上的阳极层2、设于阳极层2上的空穴注入层3、设于空穴注入层3上的电子阻挡层4、设于电子阻挡层4上的有机发光层5、设于有机发光层5上的空穴阻挡层6、设于空穴阻挡层6上的电子注入层7、设于电子注入层7上的阴极层8。
实施例14
按照与实施例12相同的步骤,将步骤5)中的化合物(式I)选为CJH-P03,得到本发明提供的器件OLED-1;
实施例15
按照与实施例12相同的步骤,将步骤5)中的化合物(式I)选为CJH-P36,得到本发明提供的器件OLED-2;
实施例16
按照与实施例12相同的步骤,将步骤5)中的化合物(式I)选为CJH-P55,得到本发明提供的器件OLED-3;
实施例17
按照与实施例12相同的步骤,将步骤5)中的化合物(式I)选为CJH-P69,得到本发明提供的器件OLED-4;
实施例18
按照与实施例12相同的步骤,将步骤5)中的化合物(式I)选为CJH-P87,得到本发明提供的器件OLED-5;
实施例19
按照与实施例12相同的步骤,将步骤5)中的化合物(式I)选为CJH-P136,得到本发明提供的器件OLED-6;
实施例20
按照与实施例12相同的步骤,将步骤5)中的化合物(式I)替换为Alq3,得到对比器件OLED-7;
所得器件的性能检测结果列于表1中,其中驱动电压、电流效率、色坐标(1931CIE)、半峰宽(FWHM)、外量子效率(EQE)是在器件的电流密度为10mA/cm2条件下得出,并且相较参比器件进行了数据归一化处理,器件的LT95%寿命是在起始亮度为10000cd/m2的条件下测得,且相较参比器件进行了数据归一化处理。
表1 OLED-1至OLED-7的性能检测结果
由上可知,本发明的有机材料制备成的器件在相同的电流密度条件下,驱动电压低,电流效率和量子效率明显比Alq3作为电子传输层的高,而且器件的LT95%寿命要好很多。
虽然,上文中已经用一般性说明、具体实施方式及试验,对本发明作了详尽的描述,但在本发明基础上,可以对其作一些修改或改进,这对本领域技术人员而言是显而易见的。因此,在不偏离本发明精神的基础上所做的这些修改或改进,均属于本发明要求保护的范围。
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