CN112521343B - 一种有机电致发光材料及其装置 - Google Patents
一种有机电致发光材料及其装置 Download PDFInfo
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- CN112521343B CN112521343B CN202011322771.4A CN202011322771A CN112521343B CN 112521343 B CN112521343 B CN 112521343B CN 202011322771 A CN202011322771 A CN 202011322771A CN 112521343 B CN112521343 B CN 112521343B
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- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/02—Seven-membered rings
- C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D267/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
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- C07D281/02—Seven-membered rings
- C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D281/08—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
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- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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Abstract
Description
技术领域
本发明属于有机电致发光元件用材料技术领域,具体涉及一种有机电致发光材料及其装置。
背景技术
最近几年有机电致发光显示技术己趋于成熟,一些产品已进入市场,但在产业化时程中,仍有许多问题亟待解决,特别是用于制作元件的各种有机材料,其载流子注入、传输性能,材料电发光性能、使用寿命、色纯度、各种材料之间及与各电极之间的匹配等,尚有许多问题还未解决。尤其是发光元件在发光效率和使用寿命还达不到实用化要求,这大大限制了OLED技术的发展。
有机电致发光主要分为荧光和磷光,但根据自旋量子统计理论,单重态激子和三重态激子的概率为1:3,即来白单重态激子辐射跃迁的荧光的理论极限为25%,三重态激子辐射跃迁的荧光的理论极限为75%。如何利用75%的三线态激子的能量成为当务之急。1997年Forrest等发现磷光电致发光现象突破了有机电致发光材料量子效率25%效率的限制,引起人们对金属配合物磷光材料的广泛关注。从此,人们对磷光材料进行大量的研究。
鉴于以上原因,特提出本发明。
发明内容
为了解决现有技术存在的以上问题,本发明提供了一种新型的有机电致发光材料,本发明的有机电致发光材料作为有机电致发光元件用材料的原料,能够提供启动电压降低、发光效率高、亮度提高的有机电致发光元件用材料以及有机电致发光元件。
为了实现上述目的,本发明采用如下技术方案:
一种有机电致发光材料,所述有机电致发光材料的结构式如式(I)所示:
其中,R1~R10相同或者不同,选自氢、氘、具有C1~C40的直链烷基、具有C1~C40的直链杂烷基、具有C3~C40的支链或环状的烷基、具有C3~C40的支链或环状的杂烷基、具有C2~C40的烯基或炔基、具有5~60个碳原子的芳香族环系或杂芳族环系中的一种,R1~R10中的每个基团可被一个或多个基团R取代,且其中两个或更多个相邻的取代基团可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系;
Ar1选自具有5~60个碳原子的芳香族环系或杂芳族环系,所述环系可被一个或多个基团R取代;
Z选自氧、硫或CR11R12;
所述R11、R12相同或者不同,选自氢、氘、具有C1~C40的直链烷基、具有C1~C40的直链杂烷基、具有C3~C40的支链或环状的烷基、具有C3~C40的支链或环状的杂烷基、具有C2~C40的烯基或炔基、具有5~60个碳原子的芳香族环系或杂芳族环系中的一种,R11、R12可被一个或多个基团R取代,且R11和R12可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系;
所述R每次出现时相同或不同,选自氢原子、氘原子、卤素原子、腈基、硝基、N(Ar2)2、N(R13)2、C(=O)Ar2、C(=O)R13、P(=O)(Ar2)2、具有C1~C40的直链烷基、具有C1~C40的直链杂烷基、具有C3~C40的支链或环状的烷基、具有C3~C40的支链或环状的杂烷基、具有C2~C40的烯基或炔基、具有5~80个碳原子的芳族环或杂芳族环系、具有5~60个碳原子的芳氧基或杂芳氧基中的一种,R基团中的每个基团可被一个或多个基团R13取代,或这些体系的组合,其中一个或多个非相邻的-CH2-基团可被R13C=CR13、C≡C、Si(R13)2、Ge(R13)2、Sn(R13)2、C=O、C=S、C=Se、C=NR13、P(=O)(R13)、SO、SO2、NR13、O、S或CONR13代替,并且其中一个或多个氢原子或被氘原子、卤素原子、腈基或硝基代替,其中两个或更多个相邻的取代基R可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系,所述环系可被一个或多个基团R13取代;
R13每次出现时相同或不同,选自氢原子、氘原子、卤素原子、腈基、硝基、N(Ar2)2、N(R14)2、C(=O)Ar2、C(=O)R14、P(=O)(Ar2)2、具有C1~C40的直链烷基、具有C1~C40的直链杂烷基、具有C3~C40的支链或环状的烷基、具有C3~C40的支链或环状的杂烷基、具有C2~C40的烯基或炔基、具有5~60个碳原子的芳族环或杂芳族环系、具有5~60个碳原子的芳氧基或杂芳氧基中的一种,R13中的每个基团可被一个或多个基团R14取代,或这些体系的组合,其中一个或多个非相邻的-CH2-基团可被R14C=CR14、C≡C、Si(R14)2、Ge(R14)2、Sn(R14)2、C=O、C=S、C=Se、C=NR14、P(=O)(R14)、SO、SO2、NR14、O、S或CONR14代替,并且其中一个或多个氢原子可被氘原子、卤素原子、腈基或硝基代替,其中两个或更多个相邻的取代基R13可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系,所述环系可被一个或多个基团R14取代;
Ar2在每次出现时相同或不同,选自具有5~30个碳原子的芳族或杂芳族环系,所述环系可被一个或多个非芳族基团R14取代;此处键合至同一氮原子或磷原子的两个基团Ar2也可通过单键或选自N(R14)、C(R14)2、氧或硫的桥连基彼此桥连;
R14选自氢原子、氘原子、氟原子、腈基、具有C1~C20的脂族烃基、具有5~30个碳原子的芳族环或杂芳族环系,其中R14中一个或多个氢原子可被氘原子、卤素原子、或腈基代替,其中两个或更多个相邻的取代基R14可彼此形成单环或多环的脂族、芳族或杂芳族环系。
在本发明意义上的芳族或杂芳族环系旨在被认为是指不必仅含有芳基或杂芳基的体系,而是其中多个芳基或杂芳基还可以由非芳族单元例如C、N、O或S原子连接。因此,例如,和其中两个或更多个芳基被例如短的烷基连接的体系一样,诸如芴、9,9’-螺二芴、9,9-二芳基芴、三芳基胺、二芳基醚等的体系也被认为是指在本发明意义上的芳族环系。
本发明意义上的芳基含有5~60个碳原子,在本发明意义上的杂芳基含有5~60个碳原子和至少一个杂原子,其条件是碳原子和杂原子的总和至少是5;所述杂原子优选选自N、O或S。此处的芳基或杂芳基被认为是指简单的芳族环,即苯、萘等,或简单的杂芳族环,如吡啶、嘧啶、噻吩等,或稠合的芳基或杂芳基,如蒽、菲、喹啉、异喹啉等。通过单键彼此连接的芳族环,例如联苯,相反地不被称为芳基或杂芳基,而是称为芳族环系。
对于本发明意义上的含有1~40个碳原子并且其中单独的氢原子或-CH2-基团还可被上述基团取代的脂族烃基或者烷基或者烯基或炔基优选被认为是指如下基团:甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、2-甲基丁基、正戊基、仲戊基、新戊基、环戊基、正己基、新己基、环己基、正庚基、环庚基、正辛基、环辛基、2-乙基己基、环己烯基、庚烯基、环庚烯基、辛烯基、环辛烯基、乙炔基、丙炔基、丁炔基、戊炔基、己炔基、庚炔基或辛炔基。烷氧基优选具有1~40个碳原子的烷氧基被认为是指甲氧基、三氟甲氧基、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、正戊氧基、仲戊氧基、2-甲基丁氧基、正己氧基、环己氧基、正庚氧基、环庚氧基、正辛氧基、环辛氧基、2-乙基己氧基、五氟乙氧基和2,2,2-三氟乙氧基。杂烷基优选具有1~40个碳原子的烷基,是指其中单独的氢原子或-CH2-基团可被氧、硫、卤素原子取代的基团,被认为是指烷氧基、烷硫基、氟代的烷氧基、氟代的烷硫基,特别是指甲氧基、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、甲硫基、乙硫基、正丙硫基、异丙硫基、正丁硫基、异丁硫基、仲丁硫基、叔丁硫基、三氟甲硫基、三氟甲氧基、五氟乙氧基、五氟乙硫基、2,2,2-三氟乙氧基、2,2,2-三氟乙硫基、乙烯氧基、乙烯硫基、丙烯氧基、丙烯硫基、丁烯硫基、丁烯氧基、戊烯氧基、戊烯硫基、环戊烯氧基、环戊烯硫基、己烯氧基、己烯硫基、环己烯氧基、环己烯硫基、乙炔氧基、乙炔硫基、丙炔氧基、丙炔硫基、丁炔氧基、丁炔硫基、戊炔氧基、戊炔硫基、己炔氧基、己炔硫基。
一般来说,根据本发明的环烷基、环烯基可为环丙基、环丁基、环戊基、环己基、环丁烯基、环戊烯基、环己烯基、环庚基、环庚烯基,其中一个或多个-CH2-基团可被上述基团代替;此外,一个或多个氢原子还可被氘原子、卤素原子或腈基代替。
根据本发明的芳族或杂芳族环原子,在每种情况下还可被上述基团R14取代的芳族或杂芳族环系,特别是指衍生自如下物质的基团:苯、萘、蒽、苯并蒽、菲、芘、苝、荧蒽、并四苯、并五苯、苯并芘、联苯、偶苯、三联苯、三聚苯、芴、螺二芴、二氢菲、二氢芘、四氢芘、顺式或反式茚并芴、顺式或反式茚并咔唑、顺式或反式吲哚并咔唑、三聚茚、异三聚茚、螺三聚茚、螺异三聚茚、呋喃、苯并呋喃、异苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、异苯并噻吩、二苯并噻吩、吡咯、吲哚、异吲哚、咔唑、吡啶、喹啉、异喹啉、吖啶、菲啶、苯并[5,6]喹啉、苯并[6,7]喹啉、苯并[7,8]喹啉、吩噻嗪、吩噁嗪、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑、菲并咪唑、吡啶并咪唑、吡嗪并咪唑、喹喔啉并咪唑、噁唑、苯并噁唑、萘并噁唑、蒽并噁唑、菲并噁唑、异噁唑、1,2-噻唑、1,3-噻唑、苯并噻唑、哒嗪、六氮杂苯并菲、苯并哒嗪、嘧啶、苯并嘧啶、喹喔啉、1,5-二氮杂蒽、2,7-二氮杂芘、2,3-二氮杂芘、1,6-二氮杂芘、1,8-二氮杂芘、4,5-二氮杂芘,4,5,9,10-四氮杂苝、吡嗪、吩嗪、吩噁嗪、吩噻嗪、荧红环、萘啶、氮杂咔唑、苯并咔啉、咔啉、菲咯啉、1,2,3-***、1,2,4-***、苯并***、1,2,3-噁二唑、1,2,4-噁二唑、1,2,5-噁二唑、1,3,4-噁二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、1,3,5-三嗪、1,2,4-三嗪、1,2,3-三嗪、四唑、1,2,4,5-四嗪、1,2,3,4-四嗪、1,2,3,5-四嗪、嘌呤、蝶啶、吲嗪和苯并噻二唑或者衍生自这些体系的组合的基团。
进一步的,所述R1~R10相同或者不同,选自氢、氘、具有5~60个碳原子的芳香族环系或杂芳族环系中的一种,所述R1~R10中的每个基团可被一个或多个基团R取代,且其中两个或更多个相邻的取代基团可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系;
进一步的,所述Ar1选自具有5~60个碳原子的芳香族环系或杂芳族环系,所述环系可被一个或多个基团R取代;
进一步的,所述Z选自氧、硫或CR11R12;
进一步的,所述R11、R12相同或者不同,选自具有C1~C40的直链烷基、具有5~60个碳原子的芳香族环系或杂芳族环系中的一种,R11、R12可被一个或多个基团R取代,且R11和R12可以任选地接合或稠合形成单环或多环的脂族、芳族或杂芳族环系;
更进一步的,所述R11、R12选自甲基、乙基、苯基;
进一步的,所述有机电致发光材料的结构如CJHP664-CJHP840所示:
其中,T1各自独立地选自*—O—*、*—S—*、或下述结构中的任一种:
本发明还保护本发明所述的有机化合物在制备有机元件用的材料中的应用。
进一步的,所述有机元件为有机电致发光元件、有机场效应晶体管或有机薄膜太阳能电池。
进一步的,针对上述有机电致发光元件,所述的有机化合在制备发光层材料、电子输送层材料、空穴输送层材料或封装层材料中的应用。
一种有机电致发光元件,包括第一电极、第二电极和位于第一电极和第二电极之间的多层有机层,所述有机层中的至少一层由本发明所述的有机化合物制备得到。
所述有机电致发光元件包含阴极、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。
在根据本发明的有机电致发光元件的其它层中,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元件,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元件,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元件,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。
进一步地,所述有机层还包括选自电子注入层、电子输送层、空穴阻挡层、电子阻挡层、空穴输送层、空穴注入层、发光层、光折射层的一种以上。
本发明的有机电致发光元件既可以是顶发射光元件,又可以是底发射光元件。本发明的有机电致发光元件的结构和制备方法没有限定。采用本发明的化合物制得的有机电致发光元件可降低启动电压、提高发光效率和亮度。
一种显示装置,包括所述的有机电致发光元件。
一种照明装置,包括所述的有机电致发光元件。
本发明的有机元件用材料含有本发明的化合物。有机元件用材料可以单独使用本发明的化合物构成,也可以同时含有其他化合物。
本发明的有机电致发光元件用材料中所含有的本发明的化合物可以用作主体材料。此时,本发明的有机电致发光元件用材料中可以含有作为掺杂材料的其他化合物。
本发明的有机电致发光元件用材料还可以作为空穴传输层、增强层、发光层、电子传输层、电荷产生层、电子阻挡层、封装层用材料。
附图说明
图1是本发明的有机电致发光装置的一个底部发光例子的示意图;
图2是本发明的有机电致发光装置的一个顶部发光例子的示意图。
图中,1-基板、2-阳极、3-空穴注入层、4-空穴传输/电子阻挡层、5-发光层、6-空穴阻挡/电子传输层、7-电子注入层、8-阴极。
具体实施方式
以下实施例用于说明本发明,但不用来限制本发明的范围。
为使本发明的目的、技术方案和优点更加清楚,下面将对本发明的技术方案进行详细的描述。显然,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有做出创造性劳动的前提下所得到的所有其它实施方式,都属于本发明所保护的范围。
以下实施例中OLED材料及元件进行性能测试的测试仪器及方法如下:
OLED元件性能检测条件:
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;
寿命测试:使用LTS-1004AC寿命测试装置。
实施例1
化合物CJHP673的制备方法,包括如下步骤:
Z1为氧或硫,T1选为C(CH3)2的化合物CJHP673-1为例:
第一步:化合物Int-1的制备
25.0mmol的1-溴-8-氟萘、30.0mmol的邻甲氧基苯胺(或邻胺基苯甲硫醚)、35.0mmol的叔丁醇钠和0.25mmol的Pd2(dba)3以及0.5mmol的Xanphos混合,再加入80mL的甲苯,在氮气保护下,升温到100℃搅拌反应12小时,冷却到室温,加入300mL的水稀释,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,得到化合物Int-1,收率84%。
第二步:化合物Int-2的制备
20.0mmol第一步制备的中间体Int-1分散在100mL聚乙二醇中,加入22.0mmol的对碘溴苯、40.0mmol的无水碳酸钾和4.0mmol的铜粉,在氮气保护下,升温至120℃搅拌反应16小时,冷却到室温,加入100mL水稀释,过滤,滤饼用水洗,再用硅胶柱分离纯化,得到白色固体化合物Int-2,收率92%。
第三步:化合物Int-3的制备
20.0mmol第二步制备的中间体Int-2溶解在120mL二氯甲烷中,在氮气保护下,用冰盐浴降温至-10℃,滴加入22.0mmol的三溴化硼溶于二氯甲烷的溶液、搅拌反应2小时,加入100mL冰冻的稀盐酸水溶液,收集有机相,干燥,过滤,滤液减压浓缩干,再用硅胶柱分离纯化,得到淡粉色固体化合物Int-3,收率94%。
第四步:化合物Int-4的制备
20.0mmol第三步制备的中间体Int-3溶解在100mL的N,N’-二甲基甲酰胺中,在氮气保护下,加入40.0mmol的无水碳酸钾和2.0mmol的铜粉,升温至130℃搅拌反应6小时,冷却到室温,过滤,将滤液倒入500mL冰水溶液中,过滤,滤饼用水洗、乙醇洗,再用硅胶柱分离纯化,得到白色固体化合物Int-4,收率83%。
第五步:化合物Int-5的制备
10.0mmol第四步制备的中间体Int-4溶解于50mL干燥的THF中,在氮气保护下,用液氮降温至-80℃,滴加入4.8mL的2.5M正丁基锂正己烷溶液,搅拌反应30分钟,再滴加入15.0mmol的硼酸三甲酯溶于THF的溶液,搅拌反应1小时,升到室温,加入20mL的3N稀盐酸水溶液,搅拌30分钟,用乙酸乙酯萃取,收集有机相,干燥,过滤,滤液减压浓缩干,加入石油醚分散,过滤,得到中间体Int-5,白色固体,收率75%。
第六步:化合物CJHP673-1(Z1为氧,T1为C(CH3)2)的制备
10.0mmol上步制备的中间体Int-5溶解于60mL的甲苯中,在氮气保护下,加入8.3mmol的N-(4-溴苯基)-9,9-二甲基芴-N-苯基-2-胺、20.0mmol的无水碳酸钾和0.01mmol的Pd(PPh3)4催化剂,升温回流搅拌反应8小时,冷却到室温,加入50mL水稀释,用二氯甲烷萃取,收集下层有机相,干燥,过滤,滤液减压浓缩干,固体用硅胶柱分离纯化,得到化合物CJHP673-1,黄色固体,收率86%。
化合物CJHP673-1的MS和1HNMR测试结果如下:
MS(MALDI-TOF):m/z 669.2924[M+H]+;1HNMR(δ、CDCl3):8.66~8.65(1H,d);8.25~8.23(1H,d);8.08~8.06(1H,d);7.66~7.49(9H,m);7.05(1H,s);7.02~6.79(9H,m);6.75~6.63(8H,m);1.44(6H,s)。
实施例2
化合物CJHP664~CJHP705、CJHP749~CJHP786、CJHP823~CJHP829、CJHP835~CJHP837中Z1为氧或硫的化合物的制备,参照实施例1中化合物CJHP673-1的制备方法,仅将不同的卤代物替换实施例1中第六步的N-(4-溴苯基)-9,9-二甲基芴-N-苯基-2-胺,其他实验参数进行常规调整,制备化合物CJHP664~CJHP705、CJHP749~CJHP786、CJHP823~CJHP829、CJHP835~CJHP837,其中Z1为氧或硫的化合物。
实施例3
化合物CJHP686的制备,包括如下步骤:
以Z1选为C(CH3)2的化合物CJHP686-1为例:
第一步:化合物Int-6的制备
10.0mmol的1,8-二溴萘溶解于80mL干燥的THF中、在氮气保护下,加入10.0mmol的叔丁醇钾,用液氮降温至-100℃,滴加入4.4mL的正丁基锂正己烷溶液,搅拌反应30分钟,滴加入11.0mmol的邻溴氯苄溶于THF的溶液,搅拌反应30分钟,升到室温搅拌反应2小时,滴加入50mL饱和氯化铵水溶液,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,得到中间体Int-6,白色晶体,收率78%。
第二步:中间体Int-7的制备
10.0mmol中间体Int-6溶解于80mL干燥的甲苯中、在氮气保护下,加入10.0mmol的对氯苯胺和30.0mmol的叔丁醇钠,再加入0.1mmol的Pd2(dba)3CHCl3和0.02mL的10%三叔丁磷甲苯溶液,升温至100℃,搅拌反应15小时,冷却到室温,加入50mL水稀释,用甲苯萃取,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-7,白色固体,收率73%。
第三步:中间体Int-8的制备
在氮气保护下,30.0mmol的氢氧化钾溶于50mL的二甲基亚砜中,在室温搅拌反应30分钟后,加入10.0mmol的中间体Int-7,搅拌反应30分钟,加入30.0mmol的碘甲烷,搅拌反应5小时,将反应液倒入200mL水中,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,得到中间体Int-8,白色固体,收率96%。
第四步:中间体Int-9的制备
参照实施例1第五步的制备方法,仅将实施例1第五步中的中间体Int-4替换为中间体Int-8,制备中间体Int-9,白色固体,收率78%。
第五步:化合物CJHP686-1的制备
参照实施例1第六步的制备方法,仅将实施例1第六步中的中间体Int-5替换为中间体Int-9,将N-(4-溴苯基)-9,9-二甲基芴-N-苯基-2-胺替换为N,N-二(4-联苯基)-N-对溴苯胺制备化合物CJHP686-1,淡黄色固体,收率86%。
化合物CJHP686-1的MS和1HNMR测试结果如下:
MS(MALDI-TOF):m/z 731.3444[M+H]+;1HNMR(δ、CDCl3):7.94~7.92(1H,d);7.81~7.78(1H,d);7.64~7.51(8H,m);7.46~7.21(14H,m);7.13~7.10(2H,m);6.97~6.88(6H,m);6.80~6.78(2H,m);6.98~6.96(2H,m);1.76(3H,s);1.64(3H,s)。
实施例4
化合物CJHP664~CJHP705、CJHP749~CJHP786、CJHP823~CJHP829、CJHP835~CJHP837中Z1为C(CH3)2的化合物的制备,参照实施例3中化合物CJHP686-1的制备方法,仅将不同的卤代物替换实施例3中第五步的N,N-二(4-联苯基)-N-对溴苯胺,其他实验参数进行常规调整,制备化合物CJHP664~CJHP705、CJHP749~CJHP786、CJHP823~CJHP829、CJHP835~CJHP837,其中Z1为C(CH3)2的化合物。
实施例5
化合物CJHP707的制备方法,包括如下步骤:
以Z1选为C(Ph)2的化合物CJHP707-1为例:
第一步:化合物Int-11的制备
10.0mmol中间体Int-10(参照实施例3中第一和第二步的合成方法制备)溶解于120mL干燥的四氯化碳中、在氮气保护下,加入20.5mmol的NBS和催化量的过氧苯甲酰,升温回流搅拌反应15小时,冷却到室温,减压浓缩干,加入120mL的二氯甲烷溶解,加入120mL的饱和碳酸钠水溶液,于室温搅拌反应2小时,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-11,白色固体,收率74%。
第二步:中间体Int-12的制备
8.0mmol第一步制备的中间体Int-11溶解于50mL干燥的THF中,在氮气保护下,用液氮降温至0℃,滴加入10.0mmol苯基锂THF的溶液,搅拌反应30分钟,升到室温,搅拌30分钟,加入20mL的1N稀盐酸水溶液,用乙酸乙酯萃取,收集有机相,干燥,过滤,滤液减压浓缩干,得到褐色的固体溶于50mL干燥的苯中,升温至回流,缓慢滴加入1.0mL的浓硫酸,继续回流反应8小时,冷却到室温,加入50mL的饱和碳酸氢钠水溶液,分出有机相,水相用甲苯萃取,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-12,白色固体,收率70%。
第三步:中间体Int-13的制备
10.0mmol第二步制备的中间体Int-12溶解于50mL干燥的THF中,加入10.0mmol的水合氯化镍和0.2g的5%钯/炭催化剂,在室温常压下通入氢气,搅拌反应12小时,过滤,滤液浓缩干,得到中间体Int-13,收率100%。
第四步:化合物CJHP707-1(Z1为C(Ph)2)的制备
10.0mmol第三步制备的中间体Int-13溶解于60mL的甲苯中,在氮气保护下,加入10.0mmol的7-溴-9,9-二甲基-N-(1-萘基)-N-苯-2-芴胺和30.0mmol的叔丁醇钠,再加入0.1mmol的Pd2(dba)3CHCl3和0.02mL的10%三叔丁磷甲苯溶液,升温至100℃,搅拌反应15小时,冷却到室温,加入50mL水稀释,用甲苯萃取,收集有机相,干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到化合物CJHP707-1,白色固体,收率76%。
化合物CJHP707-1的MS和1HNMR测试结果如下:
MS(MALDI-TOF):m/z 793.3601[M+H]+;1HNMR(δ、CDCl3):8.14~8.12(2H,m);7.89~7.87(1H,m);7.78~7.74(2H,t);7.65~7.42(10H,m);7.38~7.27(15H,m);7.24~7.20(2H,m);7.17~7.14(4H,m);7.12~7.07(2H,m);1.45(6H,s)。
实施例6
化合物CJHP664~CJHP795、CJHP823~CJHP837中Z1为C(Ph)2的化合物的制备,参照实施例5的制备方法,将不同的卤代物替换实施例5中第四步的7-溴-9,9-二甲基-N-(1-萘基)-N-苯-2-芴胺,其他实验参数进行常规的调整,制备化合物式I中的化合物CJHP664~CJHP795、CJHP823~CJHP837,其中Z1为C(Ph)2的化合物。
实施例7
化合物CJHP706~CJHP748、CJHP787~CJHP795、CJHP830~CJHP834中Z1为氧或硫的化合物的制备,参照实施例1的制备方法,将不同的卤代物替换实施例1中第六步的N-(4-溴苯基)-9,9-二甲基芴-N-苯基-2-胺,其他实验参数进行常规的调整,制备化合物式I中的化合物CJHP706~CJHP748、CJHP787~CJHP795、CJHP830~CJHP834,其中Z1为氧或硫的化合物。
实施例8
化合物CJHP706~CJHP748、CJHP787~CJHP795、CJHP830~CJHP834中Z1为C(CH3)2的化合物的制备,参照实施例3中化合物CJHP686-1的制备方法,仅将不同的卤代物替换实施例3中第五步的N,N-二(4-联苯基)-N-对溴苯胺,其他实验参数进行常规调整,制备化合物CJHP664~CJHP705、CJHP749~CJHP786、CJHP823~CJHP829、CJHP835~CJHP837,其中Z1为C(CH3)2的化合物。
实施例9
化合物CJHP822的制备方法,包括如下步骤:
Z1为氧或硫的化合物CJHP822-1为例:
第一步:化合物Int-15的制备
10.0mmol中间体Int-14(参照实施例1中第一至第四步的合成方法制备)溶解于60mL干燥的THF中、在氮气保护下,用冰水浴降温至0℃,加入11.0mmol的65%氢化钠固体,搅拌反应1小时,加入10.5mmol的2,4-二氯-6-苯基-1,3,5-三嗪,搅拌反应24小时,加入50mL水稀释,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,得到中间体Int-15,白色固体,收率64%。
第二步:化合物CJHP822-1(Z1为硫)的制备
10.0mmol上步制备的中间体Int-15溶解于60mL的甲苯中,在氮气保护下,加入12.0mmol的(3'-(9-咔唑基)-[1,1'-联苯]-4-基)硼酸、20.0mmol的无水碳酸钾和0.01mmol的Pd(PPh3)4催化剂,升温回流搅拌反应8小时,冷却到室温,加入50mL水稀释,用二氯甲烷萃取,收集下层有机相,干燥,过滤,滤液减压浓缩干,固体用硅胶柱分离纯化,得到化合物CJHP822-1,黄色固体,收率65%。
化合物CJHP822-1(Z1为硫)的MS和1HNMR测试结果如下:
MS(MALDI-TOF):m/z 722.2394[M+H]+;1HNMR(δ、CDCl3):8.48~8.46(2H,d);8.24~8.22(2H,d);8.12~8.10(2H,m);7.94~7.86(4H,m);7.58~7.52(3H,m);7.44~6.23(15H,m);7.15~7.12(2H,m);7.04(1H,s)。
实施例10
化合物CJHP796~CJHP822的制备,参照实施例9中化合物CJHP822-1的制备方法,仅将不同的卤代物替换实施例9中第二步的(3'-(9-咔唑基)-[1,1'-联苯]-4-基)硼酸,其他实验参数进行常规调整,制备化合物CJHP796~CJHP822。
实施例11
化合物CJHP838的制备方法,包括如下步骤:
以Z1为C(CH3)2的化合物CJHP838-1为例:
第一步:化合物Int-17的制备
10.0mmol中间体Int-16(参照实施例1和实施例5的合成方法制备)溶解于60mL干燥的甲苯中、在氮气保护下,加入11.0mmol的4,4’-二溴二苯硫醚和45.0mmol的叔丁醇钠,再加入0.2mmol的Pd2(dba)3CHCl3和0.04mL的10%三叔丁磷甲苯溶液,升温至100℃,搅拌反应24小时,冷却到室温,加入50mL水稀释,用甲苯萃取,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-17,白色固体,收率58%。
第二步:化合物CJHP838-1(Z1为C(CH3)2)的制备
10.0mmol第一步制备的中间体Int-17溶解于120mL的二氯甲烷中,加入40.0mmol的85%间氯过氧苯甲酸,升温回流搅拌反应12小时,冷却到室温,过滤,滤液用碳酸氢钠水溶液洗,收集有机相,干燥,过滤,滤液减压浓缩干,用硅胶柱分离纯化,得到化合物CJHP838-1,白色固体,收率92%。
化合物CJHP838-1的MS和1HNMR测试结果如下:
MS(MALDI-TOF):m/z 732.2705[M]+;1HNMR(δ、CDCl3):7.96~7.94(2H,d);7.79~7.77(2H,d);7.61~7.59(4H,m);7.48~7.36(10H,m);7.15~7.13(2H,m);6.99~6.92(8H,m);1.76(3H,s);1.74(3H,s);1.66(3H,s);1.64(3H,s)。
实施例12
化合物CJHP838~CJHP840的制备,参照实施例11的制备方法,将不同的中间体替换实施例11中第一步的中间体Int-16,制备化合物式I中的化合物CJHP838~CJHP840。
对比例1
将下述的化合物A作为绿光主体材料,使用下述的化合物B作为绿光掺杂材料,化合物C作为空穴注入材料,化合物D作为空穴传输材料,化合物G作为电子传输掺杂材料,LiQ作为电子传输主体材料。
试验例1
将对比例1中的化合物A替换为本发明的化合物CJHP664-CJHP840,按照对比例1的方法制备有机电致发光元件。
所得有机电致发光元件的性能检测结果列于表1中,其中驱动电压(V)、电流效率(LE)、色坐标(CIE)、半峰宽(FWHM)是在元件的电流密度为10mA/cm2条件下得出,且电压、LE、FWHM和LT90%相较参比元件进行了数据归一化处理。
表1元件性能检测结果
由表1可知,本发明的有机材料制备成的元件相较于对比例1制备的元件,驱动电压基本相同,但在2000cd/cm2为初始的条件下的元件寿命有很大提高,尤其是CJHP822-1在电流效率和元件寿命方面有很好的表现。
表1中仅列举了部分的CJHP664-CJHP840中部分化合物的性能,其他化合物性能与表中列举的化合物的结构基本一致,由于篇幅有限,不再一一列举。
试验例2
将对比例1中的化合物D替换为本发明的化合物CJHP664-CJHP840,按照对比例1的方法制备有机电致发光元件。
所得元件的性能检测结果列于表2中,其中驱动电压(V)、电流效率(LE)、色坐标(CIE)、半峰宽(FWHM)是在元件的电流密度为10mA/cm2条件下得出,且电压、LE、FWHM和LT90%相较参比元件进行了数据归一化处理。
表2元件性能检测结果
由表2的元件性能测试结果可知,本发明的有机材料制备成的元件相较于对比例1制备的元件尤其是CJHP686-1驱动电压明显降低,电流效率高,而且在元件初始亮度为2000cd/cm2为初始的条件下的LT90%寿命提高明显。
表2中仅列举了CJHP664-CJHP840中部分化合物的性能,其他化合物性能与表中列举的化合物的结构基本一致,由于篇幅有限,不再一一列举。
如图1和2所示,分别为本发明的有机电致发光装置的一个底部发光例子的示意图和有机电致发光装置的一个顶部发光例子的示意图,本发明制备的有机化合物包含在发光层5中或空穴传输层4中或空穴阻挡层6中。
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,可以对之作一些修改或改进,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。
Claims (7)
2.一种权利要求1所述的有机化合物作为有机元件的材料在制备有机元件中的应用。
3.根据权利要求2所述的应用,其特征在于,所述的有机元件为有机电致发光元件、有机场效应晶体管或有机薄膜太阳能电池。
4.根据权利要求3所述的应用,其特征在于,所述的有机化合物在有机电致发光元件中用作发光层材料、空穴输送层材料、空穴阻挡层材料或封装层材料。
5.一种有机电致发光元件,其特征在于,包括第一电极、第二电极和位于第一电极和第二电极之间的多层有机层,所述有机层中的至少一层由权利要求1所述的有机化合物制备得到。
6.一种显示装置,其特征在于,包括权利要求5所述的有机电致发光元件。
7.一种照明装置,其特征在于,包括权利要求5所述的有机电致发光元件。
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