CN107936957B - 有机电致发光化合物、有机电致发光器件及其应用 - Google Patents
有机电致发光化合物、有机电致发光器件及其应用 Download PDFInfo
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- CN107936957B CN107936957B CN201711430609.2A CN201711430609A CN107936957B CN 107936957 B CN107936957 B CN 107936957B CN 201711430609 A CN201711430609 A CN 201711430609A CN 107936957 B CN107936957 B CN 107936957B
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- 238000006243 chemical reaction Methods 0.000 description 97
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Classifications
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
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- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
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- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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Abstract
本发明提供了有机电致发光化合物、有机电致发光器件及其应用。本发明有机电致发光化合物结构如下:
Description
技术领域
本发明涉及发光材料领域,具体而言,涉及有机电致发光化合物、有机电致发光器件及其应用。
背景技术
目前,大部分平板显示屏为液晶显示屏(LCD,liquid crystal display),但是在全世界范围内一直在积极努力地开发更为经济、性能更加优越,同时与液晶显示屏具有差别的新型平板显示屏。最近,作为下一代平板显示屏而受到瞩目的有机电致发光器件,与液晶显示屏相比,具有自发光、广视角、驱动电压低、响应速度快、可实现柔性显示灯等诸多优点。自从20世纪80年代发明以来,有机电致发光器件已经在产业上有所应用,比如用于相机、计算机、手机、电视机显示器等,由于各界多年来的持续投入和不懈努力,有机电致发光技术已经有了极大的发展。尽管如此,寿命短、效率低等诸多问题依旧制约着有机电致发光器件的发展。
有机电致发光器件由基板、阳极、从阳极接收空穴的空穴注入层、用于传输空穴的空穴传输层、阻止电子发光层进入到空穴传输层的电子阻隔层、空穴和电子相结合而发光的发光层、组织空穴从发光层进入到电子传输层的空穴阻隔层、从阴极接收电子的电子注入层以及阴极构成。
有机电致发光器件的驱动原理如下:向上述阳极和阴极之间施加电压时,从阳极注入的空穴就要经由空穴注入层和空穴传输层移动到发光层。同时,电子从阴极经由电子注入层和电子传输层,注入到发光层,在发光层中与载流子再结合而形成激子。激子在此状态下变化为基态,由此,发光层的荧光性分子发光,形成画像。此时,激发态通过单重激发态回到基态,所发出来的光叫做“荧光”;通过三重激发态回到基态,所发出来的光叫做“磷光”。通过单重激发态回到基态的概率为25%,通过三重激发态回到基态的概率为75%,因此,发光效率有限;使用磷光的话,三重态75%和单重激发态25%都可以用来发光,因此,理论上来说,内部量子效率可以达到100%。磷光发光层由主体材料和掺杂材料组成。掺杂材料从主体材料接收能量而发光。掺杂材料可以包括例如铱金属化合物的化合物。特别是,已经研制出(4,6-F2ppy)2Irpic(79APPL.PHYS.LETT.,3082-3084(2001))和基于氟化ppy配体结构的铱化合物(CHEM.COMMUN.,1494-1495(2001))作为蓝色发光化合物,而4,4′-N,N′-二咔唑基-联苯(CBP)材料已被广泛用作主体材料。CBP的三重能带间隙足以产生绿光和红光,但是其能带间隙太小而不能在放热跃迁时产生蓝光。由于CBP主体不能放热发出蓝光,所以可能产生低发蓝光效率和寿命短的问题。
为了克服上述缺陷,已经使用了具有比CBP化合物更大的三重态能带间隙的mCP(1,3-双咔唑基-9-基-苯)化合物,然而其具有很低的分子量和低的稳定性。因此,获得具有低驱动电压、高效率、良好稳定性和寿命长的蓝色发光化合物成为了人们的研究重点。
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有机电致发光化合物,本发明有机电致发光化合物能够进一步用以制备有机电致发光器件,并降低期间的启动电压,提高器件的发光效率、稳定性。
本发明的第二目的在于提供一种有机电致发光器件,其包含本发明有机电致发光化合物。
本发明的第三目的在于提供一种本发明所述的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:
一种有机电致发光化合物,所述有机电致发光化合物的结构如下:
其中,式(I)中,R1为氢,C1~C20的直连或支链烷基,苯基,苯胺基,二苯基胺基,2-苯基-3-氨基吡啶基,3-氨基二吡啶基,2-苯基-1-萘胺基,2-胺基二萘基,2-苯基-1-胺基非基,3-胺基二菲基,2-苯基-1-胺基蒽基,2-胺基二蒽基,菲啶基,联苯基,基吡啶基,嘧啶基,或是三嗪基的一种;
R2为H,D,F,Cl,Br,I,CN,Si(R2)3,具有1~40个碳元素的直链型烷基,烷氧基,硫代基,碳原子数为3~40个碳原子的盆地型烷基或环型烷基,烷氧基,硫代基,苯基,萘基,菲基,芴基,螺二芴基,二苯并呋喃基,硫芴基,或是由其中2个或更多个相同或不同的基团所组成的具有6~60个芳香族环原子的芳基或芳杂环基、具有5~60个芳香族环原子的芳氧基,或是具有5~60个芳香族环原子的芳烷基;
R3为D,C1~C20直链或支链烷基,苯基,吡啶基,萘基,菲基,蒽基,菲啶基,联苯基,吡啶基,嘧啶基或是三嗪基的一种,
m,n各自独立为0~4的整数。
优选的,本发明所述的有机电致发光化合物中,当R1为苯基,苯胺基,二苯基胺基,2-苯基-3-氨基吡啶基,3-氨基二吡啶基,2-苯基-1-萘胺基,2-胺基二萘基,2-苯基-1-胺基非基,3-胺基二菲基,2-苯基-1-胺基蒽基,2-胺基二蒽基,菲啶基,联苯基,基吡啶基,嘧啶基,或是三嗪基时,其中至少一个氢原子可以被C1~C20的直链或支链烷基,C3~C24环烷基,C1~C20烷氧基,卤素,CN,CF3,Si(CH3)3,萘基,蒽基,菲基,二苯并呋喃基,芴基,咔唑基,螺芴基和原子数5~20杂芳基所取代或非取代。
优选的,本发明所述的有机电致发光化合物中,当R1为苯基,吡啶基,萘基,菲基,蒽基,菲啶基,联苯基,吡啶基,嘧啶基或是三嗪基时,其中至少一个氢原子被C1~C20直链或支链烷基,C3~C24环烷基,C1~C20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,螺芴基和原子数为5~20个杂芳基取代或非取代。
优选的,本发明所述的有机电致发光化合物为如下化合物的任一种:
同时,本发明还提供了一种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。
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,或者电子传输层中的至少一层包含权利要求1-4中任一项所述的有机电致发光化合物。
进一步的,本发明也提供了一种包含本发明所述的有机电致发光器件的有机电致发光显示设备。
同样的,本发明还提供了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而应用于有机电致发光器件中,并能够制造具有低驱动电压、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。
有鉴于有机电致发光化合物对于器件和显示装置的性能和使用寿命等的影响较大,而现有有机电致发光化合物无法满足实际使用需求的实际问题,本发明特提供了一种新型有机电致发光化合物,以及包含其的器件和装置,通过使用本发明有机电致发光化合物,可以有效降低器件的驱动电压,从而使得相应的设备具有高效率、良好的稳定性和长使用寿命等优点。
具体的,本发明所提供的有机电致发光化合物结构如下:
式(I)中,R1为氢,C1~C20的直连或支链烷基,苯基,苯胺基,二苯基胺基,2-苯基-3-氨基吡啶基,3-氨基二吡啶基,2-苯基-1-萘胺基,2-胺基二萘基,2-苯基-1-胺基非基,3-胺基二菲基,2-苯基-1-胺基蒽基,2-胺基二蒽基,菲啶基,联苯基,基吡啶基,嘧啶基,或是三嗪基的一种;
其中,当R1为苯基,苯胺基,二苯基胺基,2-苯基-3-氨基吡啶基,3-氨基二吡啶基,2-苯基-1-萘胺基,2-胺基二萘基,2-苯基-1-胺基非基,3-胺基二菲基,2-苯基-1-胺基蒽基,2-胺基二蒽基,菲啶基,联苯基,基吡啶基,嘧啶基,或是三嗪基时,该所述的苯基,苯胺基,二苯基胺基,2-苯基-3-氨基吡啶基,3-氨基二吡啶基,2-苯基-1-萘胺基,2-胺基二萘基,2-苯基-1-胺基非基,3-胺基二菲基,2-苯基-1-胺基蒽基,2-胺基二蒽基,菲啶基,联苯基,基吡啶基,嘧啶基,或是三嗪基上的一个或者两个及以上的氢原子可以被C1~C20的直链或支链烷基,C3~C24环烷基,C1~C20烷氧基,卤素,CN(腈基),CF3(三氟甲基),Si(CH3)3(三甲基硅基),萘基,蒽基,菲基,二苯并呋喃基,芴基,咔唑基,螺芴基和原子数5~20杂芳基所取代,从而形成具有取代或非取代结构的苯基,苯胺基,二苯基胺基,2-苯基-3-氨基吡啶基,3-氨基二吡啶基,2-苯基-1-萘胺基,2-胺基二萘基,2-苯基-1-胺基非基,3-胺基二菲基,2-苯基-1-胺基蒽基,2-胺基二蒽基,菲啶基,联苯基,基吡啶基,嘧啶基,或是三嗪基;
R2为H,D,F,Cl,Br,I,CN,Si(R2)3(例如三甲基硅基等三烷基硅基,该烷基的定义与R2相同),具有1~40个碳元素的直链型烷基,烷氧基,硫代基,碳原子数为3~40个碳原子的盆地型烷基或环型烷基,烷氧基,硫代基,苯基,萘基,菲基,芴基,螺二芴基,二苯并呋喃基,硫芴基;
或者,R2还可以为如上所述的H,D,F,Cl,Br,I,CN,Si(R2)3,具有1~40个碳元素的直链型烷基,烷氧基,硫代基,碳原子数为3~40个碳原子的盆地型烷基或环型烷基,烷氧基,硫代基,苯基,萘基,菲基,芴基,螺二芴基,二苯并呋喃基,硫芴基中的两个或者更多个基团(例如2、3、4,或者5个基团,每种情况下,各个基团可以为相同或者不同)所组成的具有6~60个芳香族环原子的芳基或芳杂环基、具有5~60个芳香族环原子的芳氧基,或是具有5~60个芳香族环原子的芳烷基;
R3为D,C1~C20直链或支链烷基,苯基,吡啶基,萘基,菲基,蒽基,菲啶基,联苯基,吡啶基,嘧啶基或是三嗪基的一种;
其中,当R3为为苯基,吡啶基,萘基,菲基,蒽基,菲啶基,联苯基,吡啶基,嘧啶基或是三嗪基时,该所述的苯基,吡啶基,萘基,菲基,蒽基,菲啶基,联苯基,吡啶基,嘧啶基或是三嗪基上的至少一个氢原子可以被C1~C20直链或支链烷基,C3~C24环烷基,C1~C20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,螺芴基和原子数为5~20个杂芳基取代,从而形成带有或者不带有取代基结构的苯基,吡啶基,萘基,菲基,蒽基,菲啶基,联苯基,吡啶基,嘧啶基或是三嗪基;
m,n各自独立为0~4的整数,例如m、n分别独立的为0、1、2、3,或者4。
而如上的有机电致发光化合物可以作为空穴传输层、电子阻隔层、空穴阻隔层、电子传输层、发光层材料,或者覆盖层材料而应用于有机电致发光器件中;
特别是作为传输层、电子阻隔层、空穴阻隔层,或者电子传输层中材料而在有机电致发光器件中使用,从而起到降低驱动电压,提高发光频率、亮度、热稳定性、色彩纯度及器件寿命的优异效果。
实施例1化合物(12)的合成
(1)中间体-1的合成
[反应式1]
将24.7g(100mmol,1.0eq.)4-溴二苯并呋喃和21.8g(110mmol,1.1eq.)3-联苯硼酸,加入到2L的三口烧瓶中,加入900ml甲苯和90ml乙醇溶解,通氮气15分钟,再加入150ml2M含有41.5g(300mmol,3.0eq.)K2CO3的水溶液,最后加入2.3g Pd(PPh3)4(2mol%)。升温至110℃,反应过夜结束。加活性炭吸附,抽滤,旋除溶剂,干燥,用甲苯和乙醇重结晶,得到26.6g中间体-1,产率为83%。
(2)中间体-2的合成
[反应式2]
在干燥的2L的三口烧瓶中,投入26.6g(83mmol,1.0eq.)反应式1得到的中间体-1,以300ml干燥的四氢呋喃溶解,通氮气,降至-10℃,滴加36.5ml 2.5M(91.3mmol,1.1eq.)的n-BuLi,待滴加结束,继续在该温度下搅拌1小时,分批加入31.6g(124.5mmol,1.5eq.)碘,移除冷却环境,继续反应过夜17小时,待反应结束,滴加4M的HCl溶液,搅拌1小时,静置,分层,上层有机相水洗3次,下层有机相以二氯甲烷萃取,水洗3次,合并有机相,干燥,旋除溶剂,用层析柱提纯,得到32.2g中间体-2,产率为87%。
(3)中间体-3的合成
[反应式3]
将32.2g(72.2mmol,1.0eq.)反应式2得到的中间体-2和10.9g(79.4mmol,1.1eq.)间氨基苯硼酸,加入到2L的三口烧瓶中,加入900ml甲苯和90ml乙醇溶解,通氮气15分钟,再加入108.3ml 2M含有30g(216.6mmol,3.0eq.)K2CO3的水溶液,最后加入1.7g Pd(PPh3)4(2mol%)。升温至110℃,反应过夜结束。加活性炭吸附,抽滤,旋除溶剂,干燥,以甲苯和乙醇重结晶,得到23.8g中间体-3,产率为80%。
(4)中间体-4的合成
[反应式4]
在干燥的2L三口烧瓶中加入23.8g(57.8mmol,1.0eq.)反应式3得到的中间体-3和18.4g(63.5mmol,1.1eq.)2-溴-5-碘噻吩,再加入干燥并除气过的800ml甲苯作溶剂,通氮气15分钟。再加入8.3g(86.7mmol,1.5eq.)叔丁醇钠,1.1g(2%mol)催化剂Pd2(dba)3和4.7ml(4%mol)P(t-bu)3的甲苯溶液(m/v,10%)。升温至90℃,反应1.5小时。待反应结束,冷却至室温,加活性炭吸附,抽滤,旋除溶剂,以甲苯和乙醇重结晶,得到25.8g中间体-4,产率为78%。
(5)中间体-5的合成
[反应式5]
将25.8g(45.1mmol,1.0eq.)反应式4得到的中间体-4和9.8g(49.6mmol,1.1eq.)3-苯基-苯硼酸,加入到2L的三口烧瓶中,加入700ml甲苯和70ml乙醇溶解,通氮气15分钟,再加入67.7ml 2M含有18.7g(135.3mmol,3.0eq.)K2CO3的水溶液,最后加入1.0g Pd(PPh3)4(2mol%)。升温至100℃,反应过夜结束。加活性炭吸附,抽滤,旋除溶剂,干燥,以甲苯和乙醇重结晶,得到22.4g中间体-5,产率为77%。
(6)化合物12的合成
[反应式6]
在干燥的2L三口烧瓶中加入22.4g(34.7mmol,1.0eq.)反应式5得到的中间体-5和9.5g(34.7mmol,1.0eq.)2-溴-9,9’-二甲基芴,再加入干燥并除气过的700ml甲苯作溶剂,通氮气15分钟。再加入6.7g(69.4mmol,2.0eq.)叔丁醇钠,0.6g(2%mol)催化剂Pd2(dba)3和2.8ml(4%mol)P(t-bu)3的甲苯溶液(m/v,10%)。升温至90℃,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,以甲苯和乙醇重结晶,得到21.8g化合物12,产率在75%。
产物核磁分析:
1H NMR(DMSO,300Hz):δ(ppm)=8.15-7.96(m,4H),7.94-7.79(m,5H),7.77-7.69(m,6H),7.60-7.35(m,17H),7.21-7.12(m,3H),6.94-6.81(d,1H),6.23-6.11(d,1H),1.79-1.48(s,6H);
MS(FAB):838(M+)。
实施例2化合物(55)的合成
(1)中间体-6的合成
[反应式7]
在干燥的2L的三口烧瓶中,投入24.7g(100mmol,1.0eq.)4-溴二苯并呋喃,以300ml干燥的四氢呋喃溶解,通氮气,降至-10℃,滴加44ml 2.5M(110mmol,1.1eq.)的LDA,待滴加结束,继续在该温度下搅拌1小时,分批加入38.1g(150mmol,1.5eq.)碘,移除冷却环境,继续反应过夜17小时,待反应结束,滴加4M的HCl溶液,搅拌1小时,静置,分层,上层有机相水洗3次,下层有机相以二氯甲烷萃取,水洗3次,合并有机相,干燥,旋除溶剂,用层析柱提纯,得到32.8g中间体-6,产率为88%。
(2)中间体-7的合成
[反应式8]
将32.8g(88mmol,1.1eq.)反应式7得到的中间体-6和17g(80mmol,1.0eq.)二苯并呋喃-4-硼酸,加入到2L的三口烧瓶中,加入1000ml甲苯和100ml乙醇溶解,通氮气15分钟,再加入120ml 2M含有33.2g(240mmol,3.0eq.)K2CO3的水溶液,最后加入1.8g Pd(PPh3)4(2mol%)。升温至100℃,反应过夜结束。加活性炭吸附,抽滤,旋除溶剂,干燥,用甲苯和乙醇重结晶,得到25.1g中间体-7,产率在76%。
(3)中间体-8的合成
[反应式9]
在干燥的2L三口烧瓶中加入25.1g(60.8mmol,1.0eq.)反应式8得到的中间体-7和17g(66.9mmol,1.1eq.)联硼酸频那醇酯,再加入干燥并除气过的800ml 1,4-二氧六环作溶剂,通氮气15分钟,加入1.0g催化剂Pd(dppf)2Cl2(2%mol)和11.9g(121.6mmol,2.0eq.)乙酸钾。升温至100℃,反应过夜5小时。待反应结束,冷却至室温,加活性炭,过硅胶短柱,旋干滤液,以甲苯和乙醇重结晶,得到23.2g中间体-8,产率为83%。
(4)中间体-9的合成
[反应式10]
将23.2g(50.5mmol,1.0eq.)反应式9中得到的中间体-8和15.7g(55.5mmol,1.1eq.)间溴碘苯,加入到2L的三口烧瓶中,加入800ml甲苯和80ml乙醇溶解,通氮气15分钟,再加入75.8ml 2M含有20.9g(151.5mmol,3.0eq.)K2CO3的水溶液,最后加入1.2gPd(PPh3)4(2mol%)。升温至100℃,反应过夜结束。加活性炭吸附,抽滤,旋除溶剂,干燥,以甲苯和乙醇重结晶,得到17.8g中间体-9,产率在72%。
(5)中间体-10的合成
[反应式11]
将25.8g(36.4mmol,1.0eq.)反应式10中得到的中间体-9和5.5g(40mmol,1.1eq.)对氨基苯硼酸,加入到2L的三口烧瓶中,加入600ml甲苯和60ml乙醇溶解,通氮气15分钟,再加入54.6ml 2M含有15.1g(109.2mmol,3.0eq.)K2CO3的水溶液,最后加入0.8g Pd(PPh3)4(2mol%)。升温至100℃,反应过夜结束。加活性炭吸附,抽滤,旋除溶剂,干燥,以甲苯和乙醇重结晶,得到14.4g中间体-10,产率为79%。
(6)中间体-11的合成
[反应式12]
在干燥的2L三口烧瓶中加入14.4g(28.8mmol,1.1eq.)反应式11中得到的中间体-10和6.1g(26.1mmol,1.0eq.)4-溴联苯,再加入干燥并除气过的400ml甲苯作溶剂,通氮气15分钟。再加入5.0g(52.2mmol,2.0eq.)叔丁醇钠,0.6g(2%mol)催化剂Pd2(dba)3和2.1ml(4%mol)P(t-bu)3的甲苯溶液(m/v,10%)。升温至90℃,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,以甲苯和乙醇重结晶,得到13g中间体-11,产率为76%。
(7)化合物55的合成
[反应式13]
在干燥的2L三口烧瓶中加入13g(19.8mmol,1.0eq.)反应式12得到的中间体-11和6.3g(19.8mmol,1.0eq.)2-(4-溴苯基)-5-苯基噻吩,再加入干燥并除气过的400ml甲苯作溶剂,通氮气15分钟。再加入5.7g(59.4mmol,3.0eq.)叔丁醇钠,0.4g(2%mol)催化剂Pd2(dba)3和1.6ml(4%mol)P(t-bu)3的甲苯溶液(m/v,10%)。升温至90℃,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,以甲苯和乙醇重结晶,得到12.1g化合物55,产率为69%。
产物核磁分析:
1H NMR(DMSO,300Hz):δ(ppm)=8.17-7.92(m,8H),7.86-7.78(m,5H),7.73-7.11(m,26H),7.04-6.87(m,2H);
MS(FAB):888(M+)。
实施例3化合物(88)的合成
(1)中间体-12的合成
[反应式14]
在干燥的2L的三口烧瓶中,投入24.4g(100mmol,1.0eq.)4-苯基二苯并呋喃,以300ml干燥的四氢呋喃溶解,通氮气,降至-10℃,滴加44ml 2.5M(110mmol,1.1eq.)的LDA,待滴加结束,继续在该温度下搅拌1小时,分批加入38.1g(150mmol,1.5eq.)碘,移除冷却环境,继续反应过夜17小时,待反应结束,滴加4M的HCl溶液,搅拌1小时,静置,分层,上层有机相用水洗3次,下层有机相以二氯甲烷萃取,水洗3次,合并有机相,干燥,旋除溶剂,层析柱提纯,得到33.3g中间体-12,产率为90%。
(2)中间体-13的合成
[反应式15]
在干燥的3L三口烧瓶中加入33.3g(90mmol,1.0eq.)反应式14得到的中间体-12和25.1g(99mmol,1.1eq.)联硼酸频那醇酯,再加入干燥并除气过的1200ml 1,4-二氧六环作溶剂,通氮气15分钟,加入1.5g催化剂Pd(dppf)2Cl2(2%mol)和17.7g(180mmol,2.0eq.)乙酸钾。升温至100℃,反应过夜5小时。待反应结束,冷却至室温,加活性炭,过硅胶短柱,旋干滤液,以甲苯和乙醇重结晶,得到28.3g中间体-13,产率为85%。
(3)中间体-14的合成
[反应式16]
将28.3g(76.5mmol,1.0eq.)反应式15得到的中间体-13和24g(84.2mmol,1.1eq.)间溴碘苯,加入到2L的三口烧瓶中,加入1000ml甲苯和100ml乙醇溶解,通氮气15分钟,再加入76.5ml 2M含有21.1g(153mmol,2.0eq.)K2CO3的水溶液,最后加入1.8g Pd(PPh3)4(2mol%)。升温至100℃,反应过夜结束。加活性炭吸附,抽滤,旋除溶剂,干燥,以甲苯和乙醇重结晶,得到22.9g中间体-14,产率为75%。
(4)中间体-15的合成
[反应式17]
将22.9g(57.4mmol,1.0eq.)反应式16得到的中间体-14和8.6g(63.1mmol,1.1eq.)对氨基苯硼酸,加入到2L的三口烧瓶中,加入600ml甲苯和60ml乙醇溶解,通氮气15分钟,再加入86.1ml 2M含有23.8g(172.2mmol,3.0eq.)K2CO3的水溶液,最后加入1.3gPd(PPh3)4(2mol%)。升温至100℃,反应过夜结束。加活性炭吸附,抽滤,旋除溶剂,干燥,以甲苯和乙醇重结晶,得到18.9g中间体-15,产率为80%。
(5)中间体-16的合成
[反应式18]
在干燥的2L三口烧瓶中加入18.9g(45.9mmol,1.1eq.)反应式17得到的中间体-15和10.7g(41.7mmol,1.0eq.)2-溴菲,再加入干燥并除气过的600ml甲苯作溶剂,通氮气15分钟。再加入8.0g(83.4mmol,2.0eq.)叔丁醇钠,0.8g(2%mol)催化剂Pd2(dba)3和3.4ml(4%mol)P(t-bu)3的甲苯溶液(m/v,10%)。升温至90℃,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,以甲苯和乙醇重结晶,得到17.6g中间体-16,产率为72%。
(6)中间体-17的合成
[反应式19]
在干燥的2L三口烧瓶中加入17.6g(30mmol,1.0eq.)反应式18得到的中间-16和9.3g(33mmol,1.1eq.)对溴碘苯,再加入干燥并除气过的500ml甲苯作溶剂,通氮气15分钟。再加入5.8g(60mmol,2.0eq.)叔丁醇钠,0.5g(2%mol)催化剂Pd2(dba)3和2.4ml(4%mol)P(t-bu)3的甲苯溶液(m/v,10%)。升温至90℃,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16.9g中间体-17,产率为76%。
(7)中间体-18的合成
[反应式20]
将32g(100mmol,1.0eq.)9,9’-二甲基芴-4-硼酸和31.8g(110mmol,1.1eq.)2-溴-5-碘-噻吩,加入到3L的三口烧瓶中,加入1200ml甲苯和120ml乙醇溶解,通氮气15分钟,再加入150ml 2M含有41.5g(300mmol,3.0eq.)K2CO3的水溶液,最后加入2.3gPd(PPh3)4(2mol%)。升温至100℃,反应过夜结束。加活性炭吸附,抽滤,旋除溶剂,干燥,以甲苯和乙醇重结晶,得到26.6g中间体-18,产率为75%。
(8)中间体-19的合成
[反应式21]
在干燥的2L三口烧瓶中加入26.6g(75mmol,1.0eq.)反应式20得到的中间体-18和21g(82.5mmol,1.1eq.)联硼酸频那醇酯,再加入干燥并除气过的1000ml 1,4-二氧六环作溶剂,通氮气15分钟,加入1.2g催化剂Pd(dppf)2Cl2(2%mol)和14.7g(150mmol,2.0eq.)乙酸钾。升温至100℃,反应过夜5小时。待反应结束,冷却至室温,加活性炭,过硅胶短柱,旋干滤液,以甲苯和乙醇重结晶,得到23.2g中间体-19,产率为77%。
(9)化合物88的合成
[反应式22]
将16.9g(22.8mmol,1.0eq.)反应式19得到的中间体-17和9.2g(22.8mmol,1.0eq.)反应式21得到的中间体-19,加入到2L的三口烧瓶中,加入500ml甲苯和50ml乙醇溶解,通氮气15分钟,再加入34.2ml 2M含有9.5g(68.4mmol,3.0eq.)K2CO3的水溶液,最后加入0.5g Pd(PPh3)4(2mol%)。升温至100℃,反应过夜结束。加活性炭吸附,抽滤,旋除溶剂,干燥,用甲苯和乙醇重结晶,得到14.1g化合物88,产率在66%。
产物核磁分析:
1H NMR(DMSO,300Hz):δ(ppm)=8.95-8.74(d,1H),8.72-8.61(d,1H),8.15-7.97(m,4H),7.94-7.79(m,5H),7.77-7.16(m,28H),7.05-6.92(m,2H),1.79-1.48(s,6H);
MS(FAB):938(M+)。
实施例4化合物(116)的合成
(1)中间体-20的合成
[反应式23]
在干燥的2L的三口烧瓶中,投入24.7g(100mmol,1.0eq.)4-溴二苯并呋喃,以300ml干燥的四氢呋喃溶解,通氮气,降至-10℃,滴加44ml 2.5M(110mmol,1.1eq.)的LDA,待滴加结束,继续在该温度下搅拌1小时,分批加入38.1g(150mmol,1.5eq.)碘,移除冷却环境,继续反应过夜17小时,待反应结束,滴加4M的HCl溶液,搅拌1小时,静置,分层,上层有机相用水洗3次,下层有机相以二氯甲烷萃取,水洗3次,合并有机相,干燥,旋除溶剂,用层析柱提纯,得到32.8g中间体-20,产率为88%。
(2)中间体-21的合成
[反应式24]
将32.8g(88mmol,1.1eq.)反应式23得到的中间体-20和17g(80mmol,1.0eq.)二苯并呋喃-4-硼酸,加入到2L的三口烧瓶中,加入1000ml甲苯和100ml乙醇溶解,通氮气15分钟,再加入120ml 2M含有33.2g(240mmol,3.0eq.)K2CO3的水溶液,最后加入1.8g Pd(PPh3)4(2mol%)。升温至100℃,反应过夜结束。加活性炭吸附,抽滤,旋除溶剂,干燥,以甲苯和乙醇重结晶,得到25.1g中间体-21,产率为76%。
(3)中间体-22的合成
[反应式25]
在干燥的2L三口烧瓶中加入25.1g(60.8mmol,1.0eq.)反应式24得到的中间体-21和17g(66.9mmol,1.1eq.)联硼酸频那醇酯,再加入干燥并除气过的800ml甲苯作溶剂,通氮气15分钟,加入1.0g催化剂Pd(dppf)2Cl2(2%mol)和11.9g(121.6mmol,2.0eq.)乙酸钾。升温至100℃,反应过夜5小时。待反应结束,冷却至室温,加活性炭,过硅胶短柱,旋干滤液,以甲苯和乙醇重结晶,得到23.2g中间体-22,产率在83%。
(4)中间体-23的合成
[反应式26]
将23.2g(50.4mmol,1.0eq.)反应式25得到的中间体-22和8.7g(50.4mmol,1.0eq.)对溴苯胺,加入到2L的三口烧瓶中,加入600ml甲苯和60ml乙醇溶解,通氮气15分钟,再加入75.6ml 2M含有20.9g(151.2mmol,3.0eq.)K2CO3的水溶液,最后加入1.2g Pd(PPh3)4(2mol%)。升温至100℃,反应过夜结束。加活性炭吸附,抽滤,旋除溶剂,干燥,以甲苯和乙醇重结晶,得到16.3g中间体-23,产率为76%。
(5)中间体-24的合成
[反应式27]
在干燥的2L三口烧瓶中加入16.3g(38.3mmol,1.1eq.)反应式26得到的中间体-23和9.0g(34.8mmol,1.0eq.)2-溴菲,再加入干燥并除气过的600ml甲苯作溶剂,通氮气15分钟。再加入6.7g(69.6mmol,2.0eq.)叔丁醇钠,0.6g(2%mol)催化剂Pd2(dba)3和2.8ml(4%mol)P(t-bu)3的甲苯溶液(m/v,10%)。升温至90℃,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14.4g中间体-24,产率在69%。
(6)化合物116的合成
[反应式28]
在干燥的2L三口烧瓶中加入14.4g(24mmol,1.0eq.)反应式27得到的中间体-24和7.6g(24mmol,1.0eq.)2-(4-溴苯基)-5-苯基噻吩,再加入干燥并除气过的400ml甲苯作溶剂,通氮气15分钟。再加入4.6g(48mmol,2.0eq.)叔丁醇钠,0.4g(2%mol)催化剂Pd2(dba)3和1.9ml(4%mol)P(t-bu)3的甲苯溶液(m/v,10%)。升温至90℃,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13g化合物116,产率为65%。
产物图谱分析:
1H NMR(DMSO,300Hz):δ(ppm)=8.96-8.79(d,1H),8.75-8.66(d,1H),8.16-7.95(m,6H),7.93-7.79(m,5H),7.77-7.12(m,22H),7.03-6.81(m,2H);
MS(FAB):836(M+)。
利用上述反应式1~28的方法,可以得到本发明通式中所涵盖的其他化合物,特别是化合物式1-120。
实验例1有机电致发光器件的制造
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HIL层沉积厚度的HAT-CN。在上述HTL层上方,将本发明中的化合物3真空蒸镀厚度形成空穴传输层。在上述空穴传输层上真空蒸镀TCTA形成的电子阻隔层,上述电子阻隔层上蒸镀能够形成blue EML的9,10-Bis(2-naphthyl)anthraces(ADN)作为发光层,作为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形成电子传输层,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。
实验例2-12
分别以化合物12、15、30、39、55、62、74、85、88、99和116作为空穴传输层(HTL)物质,其他部分与实施例1一致,据此制作出实验例2~12的有机电致发光器件。
比较例1
与实验例1的区别在于,使用NPD代替本发明的化合物作为空穴传输层,其余与实验例1相同。
上述实施例制造的有机电致发光器件及比较例制造的有机电致发光器件的特性是在电流密度为10mA/cm2的条件下测定的,结果如表1所示。
表1不同实验组器件性能测试结果:
由如上表1的实验对比数据可知,采用本发明所述的化合物制备的有机电致发光器件的实验例1~12,与对照例相比,发光效率显著提高。由此可见,本发明的化合物能使器件的驱动电压降低,减少了电能的消耗。另外通过低电力驱动,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 (7)
2.一种包含权利要求1所述的有机电致发光化合物的有机电致发光器件。
3.根据权利要求2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。
4.根据权利要求3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所述的有机电致发光化合物。
5.根据权利要求4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,或者电子传输层中的至少一层包含权利要求1所述的有机电致发光化合物。
6.一种包含权利要求3-5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。
7.权利要求1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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