CN108084180A - 一种新型有机电致发光化合物及使用该有机电致发光化合物的有机电致发光器件 - Google Patents
一种新型有机电致发光化合物及使用该有机电致发光化合物的有机电致发光器件 Download PDFInfo
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- CN108084180A CN108084180A CN201711429858.XA CN201711429858A CN108084180A CN 108084180 A CN108084180 A CN 108084180A CN 201711429858 A CN201711429858 A CN 201711429858A CN 108084180 A CN108084180 A CN 108084180A
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- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 1
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- 229910052731 fluorine Inorganic materials 0.000 description 1
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- 150000002460 imidazoles Chemical class 0.000 description 1
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- 229910052738 indium Inorganic materials 0.000 description 1
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
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- 239000011368 organic material Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
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- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 150000003413 spiro compounds Chemical class 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000004078 waterproofing Methods 0.000 description 1
Classifications
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Abstract
本发明提供了一种新型有机电致发光化合物及使用该有机电致发光化合物的有机电致发光器件。其结构如下:其中,R1,R2和R4各自独立地为C1‑C20的直链或支链型烷基、苯基、吡啶基、萘基、菲基、蒽基、菲啶基、联苯基、嘧啶基、三嗪基;R3为C1‑C10的烷基,或者C6‑C30的芳基;R5为氢、重氢、卤素、C1‑C20的直链或支链烷基,或者选自于C6‑C30的芳基组成的群;R6、R7为氘,C1‑C20的直链或支链烷基、苯基、吡啶基、萘基、菲基、蒽基、菲啶基、联苯基、嘧啶基、三嗪基;X,Y分别为C或N,I为0‑4的整数,m,n为0或1。本发明有机电致发光化合物可用于制备有机电致发光器件备,并能够可降低器件的驱动电压,提高器件的发光效率、亮度、热稳定性、色彩纯度及寿命。
Description
技术领域
本发明涉及有机电致发光材料领域,具体而言,涉及一种新型有机电致发光化合物及使用该有机电致发光化合物的有机电致发光器件。
背景技术
有机电致发光器件(Organic Light-emitting Devices,OLED)是利用如下原理的自发性发光器件:当施加电场时,荧光物质通过正极注入的空穴和负极注入的电子的重新结合而发光。这种自发光器件,具有电压低、亮度高、视角宽、响应快、温度适应性好等特性,并且具有超薄,能制作在柔性面板上等优点,广泛应用于手机、平板电脑、电视、照明等领域。
有机电致发光器件具有类似于三明治的结构,包括电极材料膜层,以及夹在不同电极膜层或者自荐的有机功能材料,各种不同功能材料根据用途相互叠加在一起共同组成有机电致发光器件。作为电流器件,当对有机电致发光器件的两端电极施加电压,并通过电场作用在有机层功能材料膜层中产生正负电荷,正负电荷进一步在发光层中复合产生光,此过程为电致发光。
对于有机电致发光器件提高性能的研究包括:降低器件的驱动电压,提高器件的发光效率,提高器件的使用寿命等。为了实现有机电致发光器件性能的不断提升,不但需要有机电致发光器件的结构和制作工艺的创新,更需要有机电致光电功能材料的不断研究和创新,创制出更高性能的有机电致功能材料。就当前有机电致发光产业的实际需求而言,目前有机电致发光材料的发展还远远不够,落后于面板制造企业的要求,作为材料型企业,开发更高性能的有机功能材料显得尤为重要。
有鉴于此,特提出本发明。
发明内容
本发明的第一目的在于提供一种型有机电致发光化合物,所述的型有机电致发光化合物具有优异的光电性能,并且能够应用于有机电致发光器件中,能够解决有机电致发光器件中驱动电压高,发光效率低、亮度、热稳定性、色彩纯度及器件寿命等问题。
本发明的第二目的在于提供一种所述的包含本发明有机电致发光化合物的有机电致发光器件。
本发明的第三目的在于提供一种本发明有机电致发光化合物的应用。
为了实现本发明的上述目的,特采用以下技术方案:
一种新型有机电致发光化合物,所述新型有机电致发光化合物结构如下:
其中,式(I)中,式(I)中,R1,R2和R4分别独立的为C1-C20的直链或支链型烷基、苯基、吡啶基、萘基、菲基、蒽基、菲啶基、联苯基、嘧啶基,或者三嗪基;R3为C1-C10的烷基,或者C6-C30的芳基;R5为氢、氘、卤素、C1-C20的直链或支链烷基,或者选自于C6-C30的芳基组成的群;R6、R7分别独立的为氘,C1-C20的直链或支链烷基、苯基、吡啶基、萘基、菲基、蒽基、菲啶基、联苯基、嘧啶基,或者三嗪基;X,Y分别独立的为C或N;I为0-4的整数;m,n分别独立的为0或1。
优选的,本发明所述的新型有机电致发光化合物中,当R1、R2、R4为苯基,吡啶基,萘基,菲基,蒽基,菲啶基,联苯基,嘧啶基或者三嗪基时,其中至少一个氢原子被C1~C20的直连或支链烷基,C3~C24的环烷基,C1~C20的烷氧基,卤素,CN,CF3,Si(CH3)3,萘基,蒽基,菲基,苯并呋喃基,二苯并呋喃基,芴基,咔唑基,螺芴基或者环原子数为5~20的杂芳基取代或非取代。
优选的,本发明所述的新型有机电致发光化合物中,当R5为C6-C30的芳基组成的群时,其中至少一个氢原子被氘、卤素、C1-C10的烷基、C2-C10的烯基、C1-C10的烷氧基、C6-C30的芳基,或者C5-C30的杂芳基取代或非取代。
优选的,本发明所述的新型有机电致发光化合物中,当R6、R7为苯基,吡啶基,萘基,菲基,蒽基,菲啶基,联苯基,嘧啶基或者三嗪基时,其中至少一个氢原子被C1~C20的直连或支链烷基,C3~C24的环烷基,C1~C20的烷氧基,卤素,CN,CF3,Si(CH3)3,萘基,蒽基,菲基,苯并呋喃基,二苯并呋喃基,芴基,咔唑基,螺芴基,或者环原子数为5~20的杂芳基取代或非取代。
优选的,本发明所述的新型有机电致发光化合物中,式(I)化合物为如下化合物中的任意一个:
同时,本发明还提供了包含本发明所述的有机电致发光化合物的有机电致发光器件。
优选的,本发明所述的有机电致发光器件包括:阳极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层以及阴极顺次堆积的构造;
其中,阳极和发光层之间还可选的设置有电子阻隔层;阴极和发光层之间还可选的设置有空穴阻隔层;阴极表面还可选的设置有覆盖层。
优选的,本发明所述的有机电致发光器件中,所述空穴传输层、电子阻隔层、空穴阻隔层、电子传输层、发光层材料,或者覆盖层中的至少一层包含本发明所述的有机电致发光化合物。
同样的,本发明也提供了包含本发明有机电致发光器件的有机电致发光显示设备。
进一步的,本发明还提供了本发明所述的有机电致发光化合物在制备有机电致发光器件中的应用;
和/或,所述的有机电致发光化合物在制备有机电致发光显示设备中的应用。
与现有技术相比,本发明的有益效果为:
本发明提供的有机电致发光化合物可以作为空穴注入层材料、空穴传输层材料、发光层材料、电子阻隔层材料及覆盖层材料使用,而以本发明有机电致发光化合物能够制得具有低驱动电压、优异的电流和功率效率以及显著改善的驱动寿命的有机电致发光器件。
具体实施方式
下面将结合实施例对本发明的实施方案进行详细描述,但是本领域技术人员将会理解,下列实施例仅用于说明本发明,而不应视为限制本发明的范围。实施例中未注明具体条件者,按照常规条件或制造商建议的条件进行。所用试剂或仪器未注明生产厂商者,均为可以通过市售购买获得的常规产品。
有鉴于现在有机电致发光器件的发展技术上还有很多不足需要改进,本发明特提供了一种新型的有机电致发光化合物。
具体的,本发明新型有机电致发光化合物结构如下:
式(I)中,式(I)中,R1,R2和R4分别独立的为C1-C20的直链或支链型烷基、苯基、吡啶基、萘基、菲基、蒽基、菲啶基、联苯基、嘧啶基,或者三嗪基;
其中,当R1,R2和R4中任意的R基为苯基,吡啶基,萘基,菲基,蒽基,菲啶基,联苯基,嘧啶基,或者三嗪基时,该所述的苯基,吡啶基,萘基,菲基,蒽基,菲啶基,联苯基,嘧啶基,或者三嗪基上的一个或两个及以上的氢原子可以被C1~C20的直连或支链烷基,C3~C24的环烷基,C1~C20的烷氧基,卤素(优选的为F、Cl、Br、I),CN(腈基),CF3(三氟甲基),Si(CH3)3(三甲基硅基),萘基,蒽基,菲基,苯并呋喃基,二苯并呋喃基,芴基,咔唑基,螺芴基或环原子数为5~20的杂芳基所取代,从而形成取代或者非取代结构的苯基,吡啶基,萘基,菲基,蒽基,菲啶基,联苯基,嘧啶基,或者三嗪基;
R3为C1-C10的烷基,或者C6-C30的芳基;
R5为氢、氘、卤素、C1-C20的直链或支链烷基,或者选自于C6-C30的芳基组成的群,例如R5可以为碳原子数为6-30的一个芳基环/稠环芳基环,或者R5可以为多个芳基,而这些芳基中碳原子的总数为30;
其中,当R5为C6~C30芳基组成的群;该所述芳基组成的群中的一个或两个及以上的氢原子可以被氘,卤素,C1~C10的烷基,C2~C10的烯基,C1~C10的烷氧基,C6~C30的芳基和C5~C30的杂芳基所取代;从而形成取代或者非取代结构的C6~C30的芳基组成的群;
R6、R7分别独立的为氘,C1-C20的直链或支链烷基、苯基、吡啶基、萘基、菲基、蒽基、菲啶基、联苯基、嘧啶基,或者三嗪基;
其中,当R6或R7中任意的R基为苯基,吡啶基,萘基,菲基,蒽基,菲啶基,联苯基,嘧啶基或者三嗪基时,该所述的苯基,吡啶基,萘基,菲基,蒽基,菲啶基,联苯基,嘧啶基,或者三嗪基上的一个或两个及以上的氢原子可以被C1~C20的直连或支链烷基,C3~C24的环烷基,C1~C20的烷氧基,卤素,CN,CF3,Si(CH3)3,萘基,蒽基,菲基,苯并呋喃基,二苯并呋喃基,芴基,咔唑基,螺芴基或环原子数为5~20的杂芳基所取代,从而形成取代或者非取代结构的苯基,吡啶基,萘基,菲基,蒽基,菲啶基,联苯基,嘧啶基,或者三嗪基;
X,Y分别独立的为C或N;
I为0-4的整数,例如I可以为0、1、2、3,或者4;
m,n分别独立的为0或1。
而如上式(I)结构的有机电致发光化合物可以作为空穴传输层材料、电子阻隔层材料、空穴阻隔层材料、电子传输层材料、主体材料或是蓝色掺杂材料等发光层材料、覆盖层材料而应用于有机电致发光器件和相应的显示设备中,从而起到降低驱动电压、提高发光效率、使用寿命等性能的目的;
优选的,本发明所提供的有机电致发光化合物可作为空穴注入层材料、空穴传输层材料、发光层材料、电子阻隔层材料及覆盖层材料使用;
更优选的,本发明所提供的有机电致发光化合物是作为空穴传输层或电子阻隔层材料而应用。
而本发明所提供的有机电致发光器件的制造方法,包括以下步骤:
步骤1,采用常规方法将阳极材料蒸镀在基板表面形成阳极,所采用的基板选择具有良好透明性、表面平滑性、操作性及防水性的玻璃基板或透明塑料基板,阳极材料可以使用透明且传导性优越的ITO、IZO、SnO2、ZnO等。
步骤2,采用常规方法将空穴注入层材料(HIL)真空热沉积或旋涂在阳极表面,空穴注入层材料可以为CuPc、m-MTDATA、m-MTDAPB、星型胺类的TCTA、2-TNATA或从日本出光兴产株式会社能够购买到的IDE406等。
步骤3,采用常规方法将空穴传输层材料(HTL)真空蒸镀或旋涂在空穴注入层表面形成空穴传输层。所述空穴传输层材料除了本发明涉及的有机化合物,还可以为α-NPD,NPB或TPD。
步骤4,采用常规方法将发光层材料(EML)真空蒸镀或旋涂在空穴传输层表面,形成发光层。所使用的发光层材料,发光主体物质可以使用本发明所述的化合物,三(8-羟基喹啉)铝(Alq3),Balq,DPVBi系列化合物,螺环化合物,螺环-DPVBi,LiPBO,双(联苯乙烯)苯,铝-喹啉金属络合物,咪唑,噻唑,恶唑的金属络合物等。
在发光层中还有与发光主体物质一起使用的掺杂物质,其为蓝光时,可以使用本发明所述的化合物;除此以外,荧光掺杂可以使用日本出光兴产株式会社的IDE102、IDE105;磷光掺杂可以使用Ir(ppy)3,FIrpic(参考文献[Chihaya Adachi et al.,Appl.Phys.Lett.,2001,79,3082-3084]),PtOEP,TBE002(Cobion公司)等。
进一步地,在空穴传输层和发光层中间还可以添加电子阻隔层(EBL)。电子阻隔层材料没有特别的限定,可以使用本发明涉及的有机化合物。
步骤5,采用常规方法将电子传输层材料(ETL)真空热沉积或旋涂在发光层表面形成电子传输层。电子传输层材料没有特别的限定,可以使用本发明涉及的有机化合物、Alq3等。
步骤6,采用常规方法将电子注入层材料(EIL)真空热沉积或旋涂在电子传输层表面,形成电子注入层。电子注入层物质可以是LiF,Liq,Li2O,BaO,NaCl,CsF等。
步骤7,采用常规方法将阴极材料真空热沉积或旋涂在电子注入层,形成阴极。阴极材料,可以为Li,Al,Al-Li,Ca,Mg,Mg-In,Mg-Ag等。另外,也可以使用氧化铟锡(ITO)或氧化铟锌(IZO)制成光透射的透明阴极。
在阴极表面还可以进一步添加覆盖层(CPL)。覆盖层材料没有特别的限定,可以使用本发明涉及的有机化合物。
进一步地,在发光层和电子传输层之间还可以添加空穴阻隔层(HBL),同时在发光层中使用磷光掺杂,可以实现防止三线态激子或空穴扩散到电子传输层的效果。采用常规方法将空穴阻隔层材料(HBL)真空热沉积或旋涂在发光层表面,形成空穴阻隔层。空穴阻隔层材料没有特别的限定,可以使用本发明涉及的有机化合物,以及Liq、2-甲基-8-羟基喹啉对羟基联苯合铝、BCP及LiF等。
实施例1化合物1的合成
中间体-1的合成
[反应式1]
在干燥的3L三口烧瓶中加入21.9g(100mmol,1.0eq.)N-苯基-2-萘胺和43.1g(120mmol,1.2eq.)的4-溴-4-碘联苯,再加入干燥并除气过的1300ml甲苯作溶剂,通氮气15分钟。再加入2.9g(15%mol)碘化亚铜,5.9g(30%mol)1,10-菲啰啉和63.7g(300mol,3eq.)的磷酸钾。升温至110℃,反应18小时。待反应结束,冷却至室温,抽滤,旋除溶剂,用甲苯和乙醇重结晶,得到37.4g的中间体-1,产率为83%。
中间体-2的合成
[反应式2]
在干燥的3L三口烧瓶中加入16.2g(83mmol,1.0eq.)吖啶酮和37.4g(83mmol,1.0eq.)的中间体-1,再加入干燥并除气过的1000ml甲苯作溶剂,通氮气15分钟。再加入16g(166mmol,2.0eq.)的叔丁醇钠,1.5g(2%mol)的催化剂Pd2(dba)3和6.7ml(4%mol)P(t-bu)3的甲苯溶液(m/v,10%)。升温至100℃,反应6小时。待反应冷却至室温,加活性炭吸附,抽滤,旋除溶剂,用甲苯和乙醇重结晶,得到38.4g的中间体-2,产率为82%。
中间体-3的合成
[反应式3]
在干燥的3L三口烧瓶中加入9.3g(100mmol,1.0eq.)苯胺和42.9g间二碘苯(130mmol,1.3eq.),再加入干燥并除气过的1000ml甲苯作溶剂,通氮气15分钟。再加入19.2g(200mmol,2.0eq.)叔丁醇钠,1.8g(2%mol)催化剂Pd2(dba)3和8.1ml(4%mol)P(t-bu)3的甲苯溶液(m/v,10%)。升温至100℃,反应2小时。待反应结束,冷却至室温,加活性炭吸附,抽滤,旋除溶剂,用甲苯和乙醇重结晶,得到23.3g的中间体-3,产率为79%。
中间体-4的合成
[反应式4]
在干燥的2L三口烧瓶中加入23.3g(79mmol)的中间体-3和23.8g(79mmol)的2-溴-1-氟-3-碘苯,再加入干燥并除气过的800ml DMF作溶剂,再缓慢加入77.2g(237mmol,3.0eq.)的碳酸铯。升温至170℃,反应过夜15小时。待反应结束,冷却至室温,加水搅拌1小时,有固体生成,抽滤,加少量乙醇冲洗,用乙醇在室温下打浆3次,抽滤,干燥得到35.5g的中间体-4,产率为62%
中间体-5的合成
[反应式5]
将实验装置充分干燥,在3L三口烧瓶中加入35.5g(61.6mmol,1.0eq.)的中间体-4,加入400ml干燥过得四氢呋喃,溶解后降温至-78℃,滴加30ml 2.5M(74mmol,1.2eq.)的n-BuLi。滴加结束后在该温度下搅拌1小时,再在该温度下滴加400ml含有34.8g中间体-2的溶液,滴加结束后室温搅拌过夜。待反应结束,加水搅拌1小时,静置分层,有机相用水洗三次,滤液用二氯甲烷萃取并水洗,合并有机相,干燥,旋除溶剂,充分干燥,再投料到2L的干燥三口烧瓶中,加入600ml乙酸和150ml浓盐酸,升温至110℃,回流过夜16小时,结束反应。冷却至室温,加入适量水,搅拌,析出固体,抽滤,水洗滤饼,再用乙醇打浆3次,最后干燥,得到41.8g的中间体-5,产率为65%。
化合物1的合成
[反应式5]
在干燥的2L的三口烧瓶中,投入41.8g(40mmol,1.0eq.)的中间体-5,用1200ml甲苯作溶剂,再投入0.2g(2%mol)的醋酸钯和11.8g(120mmol,3.0eq.)的醋酸钾,升温至110℃,反应5小时。冷却至室温,加入活性炭搅拌1小时,填硅胶过短柱,滤液旋干,用甲苯和乙醇重结晶,得到22.7g的化合物1,产率72%。
以下为化合物1的图谱检测数据:
1H NMR(DMSO,300Hz):δ(ppm)=7.96-7.68(m,2H),7.65-7.52(m,9H),7.49-7.30(m,15H),7.28-6.89(m,11H);
MS(FAB):787(M+)。
实施例2化合物37的合成
中间体-6的合成
[反应式6]
在干燥的3L三口烧瓶中加入18.4g(120mmol,1.2eq.)4-氨基联苯和24.7g 2-溴二苯并呋喃(100mmol,1.0eq.),再加入干燥并除气过的900ml甲苯作溶剂,通氮气15分钟。再加入19.2g(200mmol,2.0eq.)叔丁醇钠,1.8g(2%mol)催化剂Pd2(dba)3和8.1ml(4%mol)P(t-bu)3的甲苯溶液(m/v,10%)。升温至100℃,反应6小时。待反应结束,冷却至室温,加活性炭吸附,抽滤,旋除溶剂,用甲苯和乙醇重结晶,得到27.2g中间体-6,产率为81%。
中间体-7的合成
[反应式7]
在干燥的3L三口烧瓶中加入18g(81mmol,1.0eq.)对碘氟苯和37.4g(81mmol,1.0eq.)中间体-6,再加入干燥并除气过的1100ml甲苯作溶剂,通氮气15分钟。再加入15.6g(162mmol,2.0eq.)叔丁醇钠,1.5g(2%mol)催化剂Pd2(dba)3和6.6ml(4%mol)P(t-bu)3的甲苯溶液(m/v,10%)。升温至100℃,反应6小时。待反应冷却至室温,加活性炭吸附,抽滤,旋除溶剂,用甲苯和乙醇重结晶,得到28.9g中间体-7,产率为83%。
中间体-8的合成
[反应式8]
在干燥的2L三口烧瓶中加入28.9g(67.2mmol)的中间体-7和13.1g(67.2mmol)吖啶酮,再加入干燥并除气过的800ml DMF作溶剂,再缓慢加入43.8g(134.4mmol,2.0eq.)碳酸铯。升温至170℃,反应过夜15小时。待反应结束,冷却至室温,加水搅拌1小时,有固体生成,抽滤,加少量乙醇冲洗,用乙醇在室温下打浆3次,抽滤,干燥得到33.7g的中间体-8,产率为83%。
中间体-9的合成
[反应式9]
在2L的三口烧瓶中,投入原料26.1g(100mmol.,1.0eq.)的2-溴代二苯甲酮,用800ml浓硫酸作溶剂,降至0℃,分批加入47.2g(210mmol,2.1eq.)的N-碘代丁二酰亚胺(NIS),反应1小时后结束,在0℃下加入1000g冰水,搅拌1小时,析出大量固体,抽滤,水洗,醇洗,干燥后用乙醇打浆3次,得到38.5g的中间体-9,产率为75%。
中间体-10的合成
[反应式10]
将实验装置充分干燥,在3L三口烧瓶中加入28.6g(55.8mmol,1.0eq.)的中间体-9,加入400ml干燥过得四氢呋喃,溶解后降温至-78℃,滴加26.8ml 2.5M(66.9mmol,1.2eq.)的n-BuLi。滴加结束后在该温度下搅拌1小时,再在该温度下滴加400ml含有33.7g(55.8mmol,1.0eq.)中间体-8的溶液,滴加结束后室温搅拌过夜。待反应结束,加水搅拌1小时,静置分层,有机相用水洗三次,滤液用二氯甲烷萃取并水洗,合并有机相,干燥,旋除溶剂,充分干燥,再投料到2L的干燥三口烧瓶中,加入600ml乙酸和150ml浓盐酸,升温至110℃,回流过夜16小时,结束反应。冷却至室温,加入适量水,搅拌,析出固体,抽滤,水洗滤饼,再用乙醇打浆3次,最后干燥,得到35.9g的中间体-10,产率为63%。
中间体-11的合成
[反应式11]
在干燥的2L的三口烧瓶中,投入35.9g(35.2mmol,1.0eq.)的中间体-10,用700ml甲苯作溶剂,再投入0.2g(2%mol)的醋酸钯和10.4g(105.6mmol,3.0eq.)醋酸钾,升温至110℃,反应5小时。冷却至室温,加入活性炭搅拌1小时,填硅胶过短柱,滤液旋干,用甲苯和乙醇重结晶,得到21.8g的中间体-11,产率为81%。
中间体-12的合成
[反应式12]
在3L的三口烧瓶中,投入21.8g(28.5mmol,1.0eq.)的中间体-11和2.9g(57mmol,2.0eq.)一水合肼,3.2g(60.7mmol,2.0eq.)KOH,用600ml二乙醇作溶剂,在110℃下反应15小时后,再在195℃下反应6小时。待反应结束,冷却至室温,有大量固体形成,抽滤,水洗,醇洗,在甲苯中重结晶,得到11.1g的中间体-12,产率为52%。
化合物37的合成
[反应式13]
在干燥的2L的三口烧瓶中,投入2.1g(8.9mmol,0.6eq.)的4-溴联苯和1.3g(8.9mmol,0.6eq.)碘苯,用100ml THF溶解后降至-78℃,滴加7.1ml(17.8mmol,1.2eq.)2.5M n-BuLi,滴加结束后在-78℃下搅拌1小时,再滴加150ml含11.1g(14.8mmol,1.0eq.)中间体-12的THF溶液,滴加结束后转移到室温反应3小时。滴加500ml水淬灭反应,静置分层,上层有机相再用水洗,干燥,旋除溶剂,用甲苯重结晶,得到7.1g的化合物37,产率为52%。
以下为化合物37的图谱检测数据:
1H NMR(DMSO,300Hz):δ(ppm)=8.21-7.95(m,2H),7.92-7.81(d,2H),7.79-7.67(m,5H),7.65-7.27(m,25H),7.24-7.05(m,6H),6.97-6.84(d,1H),2.41-2.13(s,3H);
MS(FAB):917(M+)。
实施例3化合物54的合成
中间体-13的合成
[反应式14]
在干燥的3L三口烧瓶中加入33g(100mmol,1.0eq.)间二碘苯和20.3g(120mmol,1.2eq.)3-氨基联苯,再加入干燥并除气过的1000ml甲苯作溶剂,通氮气15分钟。再加入19.2g(200mmol,2.0eq.)叔丁醇钠,1.8g(2%mol)催化剂Pd2(dba)3和8.1ml(4%mol)P(t-bu)3的甲苯溶液(m/v,10%)。升温至100℃,反应2小时。待反应冷却至室温,加活性炭吸附,抽滤,旋除溶剂,用甲苯和乙醇重结晶,得到31.9g的中间体-13,产率为86%。
中间体-14的合成
[反应式15]
在干燥的3L三口烧瓶中加入31.9g(86mmol,1.0eq.)的中间体-13和25.9g(86mmol,1.0eq.)的2-溴-1-氟-3-碘苯,再加入干燥并除气过的1200ml DMF作溶剂,再缓慢加入84.1g(258mmol,3.0eq.)碳酸铯。升温至170℃,反应过夜15小时。待反应结束,冷却至室温,加水搅拌1小时,有固体生成,抽滤,加少量乙醇冲洗,用乙醇在室温下打浆3次,抽滤,干燥得到45.4g的中间体-14,产率为81%。
中间体-15的合成
[反应式16]
在干燥的3L三口烧瓶中加入41.1g(100mmol,1.0eq.)3-(4-氨基联苯基)9-苯基咔唑和22.2g(100mmol,1.0eq.)对碘氟苯,再加入干燥并除气过的1200ml甲苯作溶剂,通氮气15分钟。再加入19.2g(200mmol,2.0eq.)叔丁醇钠,1.8g(2%mol)催化剂Pd2(dba)3和8.1ml(4%mol)P(t-bu)3的甲苯溶液(m/v,10%)。升温至100℃,反应6小时。待反应冷却至室温,加活性炭吸附,抽滤,旋除溶剂,用甲苯和乙醇重结晶,得到41.4g的中间体-15,产率为82%。
中间体-16的合成
[反应式17]
在干燥的3L三口烧瓶中加入41.4g(82mmol,1.0eq.)的中间体-15和16g(82mmol)吖啶酮,再加入干燥并除气过的1200ml DMF作溶剂,再缓慢加入80.2g(246mmol,3.0eq.)碳酸铯。升温至170℃,反应过夜15小时。待反应结束,冷却至室温,加水搅拌1小时,有固体生成,抽滤,加少量乙醇冲洗,用乙醇在室温下打浆3次,抽滤,干燥得到44g的中间体-16,产率为79%。
中间体-17的合成
[反应式18]
将实验装置充分干燥,在3L三口烧瓶中加入44g(64.7mmol,1.0eq.)中间体-16,加入400ml干燥过得四氢呋喃,溶解后降温至-78℃,滴加31.1ml2.5M(77.7mmol,1.2eq.)的n-BuLi。滴加结束后在该温度下搅拌1小时,再在该温度下滴加400ml含有42.2g(64.7mmol,1.0eq.)中间体-14的溶液,滴加结束后室温搅拌过夜。待反应结束,加水搅拌1小时,静置分层,有机相用水洗三次,滤液用二氯甲烷萃取并水洗,合并有机相,干燥,旋除溶剂,充分干燥,再投料到2L的干燥三口烧瓶中,加入600ml乙酸和150ml浓盐酸,升温至110℃,回流过夜16小时,结束反应。冷却至室温,加入适量水,搅拌,析出固体,抽滤,水洗滤饼,再用乙醇打浆3次,最后干燥,得到42.8g的中间体-17,产率为58%。
化合物54的合成
[反应式19]
在干燥的2L的三口烧瓶中,投入42.8g(37.5mmol,1.0eq.)的中间体-17,用1200ml甲苯作溶剂,再投入0.2g(2%mol)的醋酸钯和11g(112.5mmol,3.0eq.)醋酸钾,升温至110℃,反应5小时。冷却至室温,加入活性炭搅拌1小时,填硅胶过短柱,滤液旋干,用甲苯和乙醇重结晶,得到25g的化合物54,产率为68%。
以下为化合物54的检测图谱数据:
1H NMR(DMSO,300Hz):δ(ppm)=8.27-8.11(d,1H),8.09-7.97(s,1H),7.94-7.86(d,1H),7.82-7.69(m,4H),7.67-6.84(m,34H),7.08-6.95(m,4H),6.58-6.43(d,1H);
MS(FAB):979(M+)。
实施例4化合物92的合成
中间体-18的合成
[反应式20]
在干燥的3L三口烧瓶中加入32.1g(100mmol,1.0eq.)二(4-氨基联苯)和22.2g对溴碘苯(100mmol,1.0eq.),再加入干燥并除气过的1200ml甲苯作溶剂,通氮气15分钟。再加入19.2g(200mmol,2.0eq.)叔丁醇钠,1.8g(2%mol)催化剂Pd2(dba)3和8.1ml(4%mol)P(t-bu)3的甲苯溶液(m/v,10%)。升温至100℃,反应6小时。待反应结束,冷却至室温,加活性炭吸附,抽滤,旋除溶剂,用甲苯和乙醇重结晶,得到34.1g的中间体-18,产率为82%。
中间体-19的合成
[反应式21]
在干燥的2L三口烧瓶中加入中间体-18 34.1g(82mmol,1.0eq.)和16g(82mmol,1.0eq.)吖啶酮,再加入干燥并除气过的1000ml DMF作溶剂,再缓慢加入53.4g(164mmol,2.0eq.)碳酸铯。升温至170℃,反应过夜15小时。待反应结束,冷却至室温,加水搅拌1小时,有固体生成,抽滤,加少量乙醇冲洗,用乙醇在室温下打浆3次,抽滤,干燥得到40.2g的中间体-19,产率为83%。
中间体-20的合成
[反应式22]
在2L的三口烧瓶中,投入原料26.1g(100mmol.,1.0eq.)2-溴代二苯甲酮,用800ml浓硫酸作溶剂,降至0℃,分批加入47.2g(210mmol,2.1eq.)N-碘代丁二酰亚胺(NIS),反应1小时后结束,在0℃下加入1000g冰水,搅拌1小时,析出大量固体,抽滤,水洗,醇洗,干燥后用乙醇打浆3次,得到38.5g的中间体-20,产率为75%。
中间体-21的合成
[反应式23]
将实验装置充分干燥,在3L三口烧瓶中加入34.9g(68.1mmol,1.0eq.)中间体-20,加入400ml干燥过得四氢呋喃,溶解后降温至-78℃,滴加32.7ml 2.5M(81.7mmol,1.2eq.)的n-BuLi。滴加结束后在该温度下搅拌1小时,再在该温度下滴加400ml含有40.2g(68.1mmol,1.0eq.)中间体-19的溶液,滴加结束后室温搅拌过夜。待反应结束,加水搅拌1小时,静置分层,有机相用水洗三次,滤液用二氯甲烷萃取并水洗,合并有机相,干燥,旋除溶剂,充分干燥,再投料到2L的干燥三口烧瓶中,加入600ml乙酸和150ml浓盐酸,升温至110℃,回流过夜16小时,结束反应。冷却至室温,加入适量水,搅拌,析出固体,抽滤,水洗滤饼,再用乙醇打浆3次,最后干燥,得到41.1g的中间体-21,产率为60%。
中间体-22的合成
[反应式24]
在干燥的2L的三口烧瓶中,投入41.1g(40.9mmol,1.0eq.)的中间体-21,用800ml甲苯作溶剂,再投入0.2g(2%mol)的醋酸钯和12g(122.7mmol,3.0eq.)醋酸钾,升温至110℃,反应5小时。冷却至室温,加入活性炭搅拌1小时,填硅胶过短柱,滤液旋干,用甲苯和乙醇重结晶,得到25.2g的中间体-22,产率82%。
中间体-23的合成
[反应式25]
在3L的三口烧瓶中,投入中间体-22 25.2g(33.5mmol,1.0eq.)和3.4g(67.1mmol,2.0eq.)一水合肼,3.8g(67.1mmol,2.0eq.)KOH,用600ml二乙醇作溶剂,在110℃下反应15小时后,再在195℃下反应6小时。待反应结束,冷却至室温,有大量固体形成,抽滤,水洗,醇洗,在甲苯中重结晶,得到13.6g的中间体-23,产率为55%。
化合物92的合成
[反应式26]
在干燥的2L的三口烧瓶中,投入4.5g(22.1mmol,1.2eq.)碘苯,用100mlTHF溶解后降至-78℃,滴加8.8ml(22.1mmol,1.2eq.)2.5Mn-BuLi,滴加结束后在-78℃下搅拌1小时,再滴加150ml含13.6g(18.4mmol,1.0eq.)中间体-23的THF溶液,滴加结束后转移到室温反应3小时。滴加500ml水淬灭反应,静置分层,上层有机相再用水洗,干燥,旋除溶剂,用甲苯重结晶,得到9.2g化合物92,产率为56%。
以下为化合物92检测图谱数据:
1H NMR(DMSO,300Hz):δ(ppm)=8.05-7.83(d,2H),7.81-7.65(m,4H),7.61-7.33(m,22H),7.31-6.95(m,16H);
MS(FAB):889(M+)。
进一步的,还可以参照如上式1-26的方法,得到本发明通式结构中的其他化合物,特别是化合物1-120。
实施例1
一种有机电致发光器件,其采用ITO作为反射层阳极基板材料,并用N2等离子或UV-Ozone对其进行表面处理。
在阳极基板上方,向空穴注入层沉积厚度的HAT-CN。在上述空穴注入层上方,选择实施例1中的化合物1真空蒸镀形成空穴传输层。在上述空穴传输层上真空蒸镀TCTA形成的电子阻隔层,上述电子阻隔层蒸镀能够形成blue EML的9,10-Bis(2-naphthyl)anthraces(ADN)作为发光层,以dopant掺杂约5%的2,5,8,11-四丁基二萘嵌苯形成的发光层。在其上方将蒽衍生物和Liq以1:1的比例混合蒸镀的厚度到电子传输层,在电子传输层之上蒸镀的Liq作为电子注入层。最后在阴极蒸镀厚度的银。此外,在阴极表面用含有UV硬化性粘合剂吸水材料密封,以保护有机电致发光器件不被大气中的氧气或水分所影响。
本实施例中所述化合物的结构式如下:
实施例2-12
分别以化合物4,19,37,45,54,63,71,79,92,97和120作为空穴传输层(HTL)物质,其他部分与实施例1一致,据此制作出实施例1~12的有机电致发光器件。
对照例1
与实施例1的区别在于,使用NPD代替本发明的有机电致发光化合物作为空穴传输层物质,其余与实施例1相同。
将实施例1~12和对照例1制备获得的有机电致发光器件在电流密度10mA/cm2,结果如下表所示。
表1实施例1-12和对照例1有机电致发光器件性能对比
由上述表1所示的实验结果可知,相较于现有的有机电致发光器件,本发明实施例1-12的有机电致发光器件在发光效率性能有明显的改进。
另外,由述实验结果可知,使用本发明的有机化合物作为空穴传输物质时,可以确认有机电致发光器件的驱动电压明显降低,本发明的有机化合物可以为器件提供降低电力驱动并减少电力消耗的效果,另外,通过更低的电力驱动,有机电致发光器件的寿命也有所提高。
尽管已用具体实施例来说明和描述了本发明,然而应意识到,在不背离本发明的精神和范围的情况下可以作出许多其它的更改和修改。因此,这意味着在所附权利要求中包括属于本发明范围内的所有这些变化和修改。
Claims (10)
1.一种新型有机电致发光化合物,其特征在于,所述新型有机电致发光化合物结构如下:
其中,式(I)中,式(I)中,R1,R2和R4分别独立的为C1-C20的直链或支链型烷基、苯基、吡啶基、萘基、菲基、蒽基、菲啶基、联苯基、嘧啶基,或者三嗪基;
R3为C1-C10的烷基,或者C6-C30的芳基;
R5为氢、氘、卤素、C1-C20的直链或支链烷基,或者选自于C6-C30的芳基组成的群;
R6、R7分别独立的为氘,C1-C20的直链或支链烷基、苯基、吡啶基、萘基、菲基、蒽基、菲啶基、联苯基、嘧啶基,或者三嗪基;
X,Y分别独立的为C或N;
I为0-4的整数;
m,n分别独立的为0或1。
2.根据权利要求1所述的新型有机电致发光化合物,其特征在于,当R1、R2、R4为苯基,吡啶基,萘基,菲基,蒽基,菲啶基,联苯基,嘧啶基或者三嗪基时,其中至少一个氢原子被C1~C20的直连或支链烷基,C3~C24的环烷基,C1~C20的烷氧基,卤素,CN,CF3,Si(CH3)3,萘基,蒽基,菲基,苯并呋喃基,二苯并呋喃基,芴基,咔唑基,螺芴基或者环原子数为5~20的杂芳基取代或非取代。
3.根据权利要求1所述的新型有机电致发光化合物,其特征在于,当R5为C6-C30的芳基组成的群时,其中至少一个氢原子被氘、卤素、C1-C10的烷基、C2-C10的烯基、C1-C10的烷氧基、C6-C30的芳基,或者C5-C30的杂芳基取代或非取代。
4.根据权利要求1所述的新型有机电致发光化合物,其特征在于,当R6、R7为苯基,吡啶基,萘基,菲基,蒽基,菲啶基,联苯基,嘧啶基或者三嗪基时,其中至少一个氢原子被C1~C20的直连或支链烷基,C3~C24的环烷基,C1~C20的烷氧基,卤素,CN,CF3,Si(CH3)3,萘基,蒽基,菲基,苯并呋喃基,二苯并呋喃基,芴基,咔唑基,螺芴基,或者环原子数为5~20的杂芳基取代或非取代。
5.根据权利要求1所述的新型有机电致发光化合物,其特征在于,式(I)化合物为如下化合物中的任意一个:
6.一种包含权利要求1-5中任一项所述的有机电致发光化合物的有机电致发光器件。
7.根据权利要求6所述的有机电致发光器件,其特征在于,所述有机电致发光器件包括:
阳极、空穴注入层、空穴传输层、发光层、电子传输层、电子注入层以及阴极顺次堆积的构造;
其中,阳极和发光层之间还可选的设置有电子阻隔层;
阴极和发光层之间还可选的设置有空穴阻隔层;
阴极表面还可选的设置有覆盖层。
8.根据权利要求7所述的有机电致发光器件,其特征在于,所述空穴传输层、电子阻隔层、空穴阻隔层、电子传输层、发光层材料,或者覆盖层中的至少一层包含权利要求1-5中任一项所述的有机电致发光化合物。
9.一种包含权利要求6-8中任一项所述的有机电致发光器件的有机电致发光显示设备。
10.权利要求1-5中任一项所述的有机电致发光化合物在制备有机电致发光器件中的应用;
和/或,权利要求1-5中任一项所述的有机电致发光化合物在制备有机电致发光显示设备中的应用。
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