WO2017080445A1 - 有机电子传输材料 - Google Patents

有机电子传输材料 Download PDF

Info

Publication number
WO2017080445A1
WO2017080445A1 PCT/CN2016/105147 CN2016105147W WO2017080445A1 WO 2017080445 A1 WO2017080445 A1 WO 2017080445A1 CN 2016105147 W CN2016105147 W CN 2016105147W WO 2017080445 A1 WO2017080445 A1 WO 2017080445A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
substituted
unsubstituted
organic
organic electron
Prior art date
Application number
PCT/CN2016/105147
Other languages
English (en)
French (fr)
Inventor
鲁锦鸿
陈金鑫
李哲
戴雷
蔡丽菲
Original Assignee
广东阿格蕾雅光电材料有限公司
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 广东阿格蕾雅光电材料有限公司 filed Critical 广东阿格蕾雅光电材料有限公司
Publication of WO2017080445A1 publication Critical patent/WO2017080445A1/zh

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • 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
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2102/00—Constructional details relating to the organic devices covered by this subclass
    • H10K2102/301—Details of OLEDs
    • H10K2102/302—Details of OLEDs of OLED structures

Definitions

  • the present invention relates to a novel organic electron transporting material which is deposited as a thin film by vacuum deposition as an electron transporting material for an electron-only semiconductor diode device.
  • Electron-only organic semiconductor diode devices are one type of single-carrier devices that are used as power semiconductor devices for switches or rectifiers of smart digital power integrated circuits.
  • the electron transporting material of the present invention can also be applied to an organic electroluminescent device and a field effect transistor.
  • Electron-only organic semiconductor diode devices are devices prepared by spin coating or depositing one or more layers of organic materials between electrodes of two metals, inorganic or organic compounds.
  • a classic layer of electronically only organic semiconductor diode device comprises an anode, an electron transport layer and a cathode.
  • a hole blocking layer may be added between the anode and the electron transporting layer of the multilayer electronic-only semiconductor diode device, and an electron injecting layer may be added between the electron transporting layer and the cathode.
  • the hole blocking layer, the electron transport layer and the electron injecting layer are respectively composed of a hole blocking material, an electron transporting material, and an electron injecting material.
  • BPhen bathophenanthroline
  • BCP bathocuproine
  • the electrical conductivity of the entire device will change after time, causing the electron and hole charge mobility to be unbalanced, resulting in a decrease in device performance and possibly localization in the device. Short circuit, affecting device stability and even device failure.
  • the mirror surface of the molecular structure is indicated by a dotted line
  • the present invention provides an organic electron transporting material which can be applied to long-life electronic-only semiconductor diode devices and organic electroluminescent devices, which has high electron transport rate, good electron transport performance, and high luminous efficiency.
  • R represents a C1-C8 alkyl group, or a C2-C8 substituted or unsubstituted olefinic group, or a C2-C8 substituted or unsubstituted alkynylalkyl group; wherein, Ar 1 and Ar 2 are independently represented as C6- C60 substituted or unsubstituted aryl.
  • R represents a C1-C4 alkyl group, or a C2-C4 substituted or unsubstituted olefinic group, or a C2-C4 substituted or unsubstituted alkynylalkyl group;
  • Ar 1 and Ar 2 are independently represented as Phenyl, naphthyl, anthracenyl, phenanthryl, anthracenyl, fluorenyl, fluorenyl, (9,9-dialkyl)fluorenyl substituted or unsubstituted by C1-C4 alkyl or C6-C30 aryl , (9,9-dialkyl substituted or unsubstituted aryl) anthracenyl or 9,9-spiropurinyl.
  • R is preferably represented by methyl, ethyl, propyl or isopropyl; wherein, Ar 1 and Ar 2 are independently represented by phenyl, tolyl, xylyl, naphthyl, methylnaphthalene, and Phenyl, diphenylphenyl, naphthylphenyl, diphenylbiphenyl, (9,9-dialkyl)fluorenyl, (9,9-dimethyl substituted or unsubstituted phenyl) fluorenyl , 9, 9-snail base.
  • Ar 1 and Ar 2 are independently represented by phenyl, tolyl, xylyl, naphthyl, methylnaphthalene, and Phenyl, diphenylphenyl, naphthylphenyl, diphenylbiphenyl, (9,9-dialkyl)fluorenyl, (9,9-dimethyl substituted or unsubstituted
  • R is preferably a methyl group.
  • Ar 1 and Ar 2 are the same.
  • the compound of the formula (I) is the following structural compound
  • An electron-only organic semiconductor diode device comprising an anode, a cathode, and an organic layer, the anode and cathode being a metal, an inorganic or an organic compound; the organic layer being a hole blocking layer, an electron transport layer, and an electron injection layer One or more layers. It is particularly noted that the above organic layers may be present in each of the layers as needed.
  • the hole blocking layer, the electron transport layer and/or the electron injecting layer contain the compound of the formula (I).
  • the compound of the formula (I) is an electron transporting material.
  • the organic layer of the electronic device of the present invention has a total thickness of from 1 to 1000 nm, preferably from 1 to 500 nm, more preferably from 5 to 300 nm.
  • the organic layer may be formed into a film by steaming or spin coating.
  • the device experiments show that only the electronic organic semiconductor diode device and the organic electroluminescent device prepared by using the organic electron transporting material of the invention emit blue, have high electron transmission rate, good electron transport performance and high luminous efficiency.
  • Figure 1 is an HPLC chart of the compound of Example 1
  • Figure 2 is a carbon spectrum of the compound of Example 1;
  • Figure 3 is a hydrogen spectrum of the compound of Example 1;
  • Figure 4 is a TGA diagram of the compound of Example 1
  • Figure 5 is a structural view of the device of the present invention.
  • 10 represents a glass substrate
  • 20 represents an anode
  • 30 represents a hole blocking layer
  • 40 represents an electron transport layer
  • 50 represents an electron injecting layer
  • 60 represents a cathode.
  • Figure 9 shows the emission spectrum
  • Reaction preparation 4,7-diphenylphenanthroline (5.0 g, 15 mmol) was added to the reaction flask, and nitrogen was added three times, then anhydrous THF (180 mL) was added, and the mixture was cooled in an ice water bath for 15 minutes, and then added to the reaction mixture. Lithium-n-hexane solution (12 ml, 15.07 mmol), the reaction mixture gradually changed from a white turbid liquid to a blue-black color until black, and the mixture was stirred at room temperature for 8 h, then stirred in air for 24 h. After the reaction was stopped, the THF was evaporated, EtOAc (EtOAc)EtOAc. The filtrate was Compound 4 (5.19 g, 99%).
  • An electron-only organic semiconductor diode device was prepared using the organic electron transport material of the present invention, see FIG.
  • the transparent conductive ITO glass substrate 10 (with the anode 20 on the surface) was sequentially washed with a detergent solution and deionized water, ethanol, acetone, deionized water, and then treated with oxygen plasma for 30 seconds.
  • a compound 4 having a thickness of 100 nm was vapor-deposited on the hole blocking layer as the electron transport layer 40.
  • lithium fluoride of 1 nm thick was vapor-deposited on the electron transport layer as the electron injection layer 50.
  • SCLC space charge limited current
  • J is the current density (mA cm -2 )
  • ⁇ is the relative dielectric constant (the organic material usually takes 3)
  • ⁇ 0 is the vacuum dielectric constant (8.85 ⁇ 10 -14 C V -1 cm -1 )
  • E is the electric field strength (V cm -1 )
  • L is the thickness (cm) of the sample in the device
  • ⁇ 0 is the charge mobility under the electric field (cm 2 V -1 s -1 )
  • ⁇ is the Poole–Frenkel factor. Indicates how quickly the mobility changes with the strength of the electric field.
  • the device produced in E electron mobility under operating electric field is 1x 10 6 Vcm -1 was 2.36x 10 -4 cm 2 V -1 s -1. Structure in the device
  • the method was the same as in Example 2 except that a commonly used commercially available compound TmPyPB was used as the electron transport layer 40, and an electron-only semiconductor diode device for comparison was fabricated.
  • the device produced in E an electron mobility under operating electric field is 1x 10 6 Vcm -1 was 1.61x 10 -6 cm 2 V -1 s -1. Structure in the device
  • the method was the same as in Example 2, except that the compound PhBPhen (synthesized according to US20080265746) was used as the electron transport layer 40, and an electron-only semiconductor diode device for comparison was fabricated.
  • the device produced in E electron mobility under operating electric field is 1x 10 6 Vcm -1 was 8.12x 10 -4 cm 2 V -1 s -1. Structure in the device
  • the fabricated device has a voltage of 3.75V at a working current density of 20 mA/cm 2 , a current efficiency of 2.93 cd/A, and a CIEy coordinate of 0.0915 at a luminance of 1000 cd/m 2 . Blu-ray.
  • the first electron transmission rate is the highest, the second is second, and the third is poor, that is, the electron transmission performance is the best.
  • the luminous efficiency of the device 1 is high.
  • the brightness and color coordinates appear to be device 1, device 2 and device 3 are similar, indicating that the chromaticity changes of several materials are basically the same, and the spectral data consistently indicates that the energy levels of HOMO and LUMO are consistent.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

一种有机电子传输材料，具有式(I)结构的化合物，其中，R表示为C1-C8烷基、或C2-C8取代或者未取代的烯烷基、或C2-C8取代或者未取代的炔烷基；Ar 1、Ar 2独立地表示为C6-C60取代或者未取代的芳基。器件实验表明，使用该有机电子传输材料制备的仅电子有机半导体二极管器件及有机电致发光器件发射蓝光，电子传输速率高，电子传输性能好，发光效率高。

Description

有机电子传输材料 技术领域
本发明涉及新型的有机电子传输材料，通过真空沉积成薄膜，作为电子传输材料应用于仅电子有机半导体二极管器件。
背景技术
仅电子有机半导体二极管器件是单载流子器件的一种，作为功率半导体装置用于智能数字功率集成电路的开关或整流器。其中本发明的电子传输材料也可应用于有机电致发光器件及场效应晶体管。
仅电子有机半导体二极管器件为在两个金属、无机物或有机化合物的电极之间通过旋涂或沉积一层或多层有机材料而制备的器件。一个经典的一层仅电子有机半导体二极管器件包含阳极，电子传输层和阴极。在多层仅电子有机半导体二极管器件阳极和电子传输层之间可以加入空穴阻挡层，而电子传输层和阴极之间可以加入电子注入层。空穴阻挡层，电子传输层和电子注入层分别由空穴阻挡材料，电子传输材料和电子注入材料组成。连接到仅电子有机半导体二极管器件的电压到达开启电压后，由阴极产生的电子经电子传输层传输到阳极，相反地,空穴不能从阳极注入。仅电子有机半导体二极管器件中的电子传输材料可应用到其它半导体器件如有机电致发光器件。有机电致发光器件市场庞大，因而稳定、高效的有机电子传输材料对有机电致发光器件的应用和推广具有重要作用，同时也是有机电致发光大面积面板显示的应用推广的迫切需求。
市场上现有较多使用的电子传输材料向红菲咯啉(bathophenanthroline,BPhen)和浴铜灵(bathocuproine,BCP)，基本上能符合有机电致发光面板的市场需求，但其效率和稳定性仍有待进一步提高。从BPhen及BCP的分子结构中分析，其对称结构会使分子倾向有规则地堆叠，时间过后容易做成结晶。电子传输材料一旦结晶，分子间的电荷跃迁机制跟在正常运作的非晶态薄膜机制不相同，引致电子传输性能改变。如果BPhen对称分子结构的材料在有机电致发光器件中使用，时间过后会使整个器件导电性能改变，令电子和空穴电荷迁移率失衡，引致到器件效能下降，也可能会在器件中产生局部短路，影响器件稳定性，甚至令器件失效。
Figure PCTCN2016105147-appb-000001
分子结构的镜面用虚线表示
发明内容
针对上述材料的缺陷，本发明提供一种可应用在长寿命仅电子有机半导体二极管器件和有机电致发光器件中电子传输速率高，电子传输性能好，发光效率高的有机电子传输材料。
有机电子传输材料，具有式(I)所述结构的化合物，
Figure PCTCN2016105147-appb-000002
其中，R表示为C1-C8烷基、或C2-C8取代或者未取代的烯烷基、或C2-C8取代或者未取代的炔烷基；其中，Ar1、Ar2独立地表示为C6-C60取代或者未取代的芳基。
优选：其中，R表示为C1-C4烷基、或C2-C4取代或者未取代的烯烷基，或C2-C4取代或者未取代的炔烷基；其中，Ar1、Ar2独立地表示为由C1-C4烷基或者C6-C30芳基取代或者未取代的苯基、萘基、蒽基，菲基，芘基，苝基，荧蒽基，(9,9-二烷基)芴基，(9,9-二烷基取代或未取代芳基)芴基或9,9-螺芴基。
优选：其中，R优选表示为甲基，乙基，丙基，异丙基；其中，Ar1、Ar2独立地表示为苯基，甲苯基，二甲苯基，萘基，甲基萘，联苯基，二苯基苯基，萘基苯基，二苯基联苯基，(9,9-二烷基)芴基，(9,9-二甲基取代或未取代苯基)芴基，9,9-螺芴基。
如上面提到的，本发明的式(I)所述的化合物如下，但不限于所列举的结构：
Figure PCTCN2016105147-appb-000003
Figure PCTCN2016105147-appb-000004
优选：R优选为甲基。
优选：Ar1、Ar2相同。
更优选：式(I)所述的化合物为下列结构化合物
Figure PCTCN2016105147-appb-000005
一种仅电子有机半导体二极管器件包含阳极，阴极，和有机层，所述阳极和阴极为金属、无机物或有机化合物；所述有机层为空穴阻挡层、电子传输层、电子注入层中的一层或多层。需要特别指出，上述有机层可以根据需要，这些有机层不必每层都存在。
所述空穴阻挡层，电子传输层和/或电子注入层中含有式(I)所述的化合物。
所述式(I)所述的化合物为电子传输材料。
本发明的电子器件有机层的总厚度为1-1000nm，优选1-500nm，更优选5-300nm。
所述有机层可以通过蒸渡或旋涂形成薄膜。
器件实验表明，使用本发明的有机电子传输材料制备的仅电子有机半导体二极管器件及有机电致发光器件发射蓝色，电子传输速率高，电子传输性能好，发光效率高。
附图说明
图1实施例1化合物的HPLC图,
图2实施例1化合物的碳谱图，
图3实施例1化合物的氢谱图，
图4实施例1化合物的TGA图，
图5为本发明的器件结构图，
其中10代表为玻璃基板，20代表为阳极，30代表为空穴阻挡层，40代表为电子传输层，50代表电子注入层，60代表为阴极。
图6电压-电流密度，
图7电流密度-电流效率，
图8亮度-色坐标y，
图9发射光谱。
具体实施方式
为了更详细叙述本发明，特举以下例子，但是不限于此。
实施例1
Figure PCTCN2016105147-appb-000006
化合物4的合成
反应投放：向反应瓶中加入4,7-二苯基菲罗啉(5.0g,15mmol)，充放氮气三次后加入无水 THF(180mL)，冰水浴降温15分钟后在反应混合物中加入甲基锂正己烷溶液(12ml，15.07mmol)，反应液由开始的白色浊状液逐渐变为蓝黑色，直至黑色，加入溶液后室温搅拌8h，然后在空气中搅拌24h。停止反应后，旋干THF，加入水(100mL)和二氯甲烷(150mL x 3)萃取，有机层合并，用无水硫酸镁干燥后过滤，滤液旋干后用丙酮(50mL)打浆，抽滤，滤质为化合物4(5.19克，99％)。真空(4x 10-5torr)加热160℃升华完成后得到3.14克黄色粉末状产品，纯度99.575％，见图1，峰值统计见下表。1H NMR(300MHz，CDCl3)δ9.21(d，J＝3Hz，1H)，7.76(s，2H)，7.52-7.46(m，12H)；13C NMR(75MHz，CDCl3)δ159.0，149.8，148.6，148.5，146.7，146.5，138.2，129.8，129.8，128.7，128.5，128.5，126.6，124.7，124.3，124.1，123.4，123.1，26.3。
峰表
PDA Ch1 254nm
峰号 保留时间 面积 高度 面积％ 高度％
1 4.042 253 35 0.003 0.005
2 5.310 3801 408 0.047 0.062
3 7.509 591 80 0.007 0.012
4 7.983 8109838 659953 99.533 99.575
5 8.703 3336 355 0.041 0.054
6 9.412 1054 82 0.013 0.012
7 10.481 25386 1632 0.312 0.246
8 11.604 3644 224 0.045 0.034
总计   8147904 662769 100.000 100.000
液相的条件如下：
色谱柱：InertSustain C18 4.6*250mm，5μm，柱温：40℃
溶剂：DCM，流动相：MeOH∶4mMNa2EDTA水溶液＝8∶2，检测波长：254nm
其氢谱、碳谱和TGA图见图2-4。
实施例2仅电子有机半导体二极管器件1的制备
使用本发明的有机电子传输材料制备仅电子有机半导体二极管器件，见图5。
首先，将透明导电ITO玻璃基板10(上面带有阳极20)依次经：洗涤剂溶液和去离子水，乙醇，丙酮，去离子水洗净，再用氧等离子处理30秒。
然后，在ITO上蒸渡5nm厚的BCP作为空穴阻挡层30。
然后，在空穴阻挡层上蒸渡100nm厚的化合物4作为电子传输层40。
然后，在电子传输层上蒸渡1nm厚的氟化锂作为电子注入层50。
最后，在电子注入层上蒸渡100nm厚的铝作为器件阴极60。
通过利用空间限制电流(space charge limited current,SCLC)电流密度与电场强度的关系如式(1)：
Figure PCTCN2016105147-appb-000007
其中，J为电流密度(mA cm-2),ε为相对介电常数(有机材料通常取值为3)，ε0为真空介电常数(8.85×10-14C V-1cm-1)，E为电场强度(V cm-1)，L为器件中样本的厚度(cm)，μ0为零电场下的电荷迁移率(cm2V-1s-1)，β为Poole–Frenkel因子，表示迁移率随电场强度变化的快慢程度。
所制备的器件在E＝1x 106Vcm-1的工作电场下的电子迁移率为2.36x 10-4cm2V-1s-1。器件中所述结构式
Figure PCTCN2016105147-appb-000008
比较例1仅电子有机半导体二极管器件2的制备
方法同实施例2，但使用常用市售化合物TmPyPB作为电子传输层40，制作对比用仅电子有机半导体二极管器件。
所制备的器件在E＝1x 106Vcm-1的工作电场下的电子迁移率为1.61x 10-6cm2V-1s-1。器件中所述结构式
Figure PCTCN2016105147-appb-000009
比较例2仅电子有机半导体二极管器件3的制备
方法同实施例2，但使用化合物PhBPhen(根据US20080265746合成)作为电子传输层40，制作对比用仅电子有机半导体二极管器件。
所制备的器件在E＝1x 106Vcm-1的工作电场下的电子迁移率为8.12x 10-4cm2V-1s-1。 器件中所述结构式
Figure PCTCN2016105147-appb-000010
如图6－图9所示，所制备的器件在20mA/cm2的工作电流密度下电压为3.75V，电流效率达到2.93.cd/A，在1000cd/m2亮度下CIEy坐标为0.0915，发射蓝光。
从器件数据对比来看，从电压电流密度曲线看，第一个的电子传输速率最高，第二个其次，第三个较差，即电子传输性能最好。从电流密度-电流效率看，器件1的发光效率高。亮度和色坐标看起来器件1，器件2和器件3差不多，说明几个材料的色度变化基本一致，光谱数据一致说明HOMO和LUMO的能级差是一致的。

Claims (8)

  1. 有机电子传输材料，具有式(I)所述结构的化合物，
    Figure PCTCN2016105147-appb-100001
    其中，R表示为C1-C8烷基、或C2-C8取代或者未取代的烯烷基、或C2-C8取代或者未取代的炔烷基；Ar1、Ar2独立地表示为C6-C60取代或者未取代的芳基。
  2. 根据权利要求1所述的有机电子传输材料，其中，R表示为C1-C4烷基、或C2-C4取代或者未取代的烯烷基，或C2-C4取代或者未取代的炔烷基；Ar1、Ar2独立地表示为由C1-C4烷基或者C6-C30芳基取代或者未取代的苯基、萘基、蒽基，菲基，芘基，苝基，荧蒽基，(9,9-二烷基)芴基，(9,9-二烷基取代或未取代芳基)芴基或9,9-螺芴基。
  3. 根据权利要求2所述的有机电子传输材料，其中，R表示为甲基，乙基，丙基，异丙基；Ar1、Ar2独立地表示为苯基，甲苯基，二甲苯基，萘基，甲基萘，联苯基，二苯基苯基，萘基苯基，二苯基联苯基，(9,9-二烷基)芴基，(9,9-二甲基取代或未取代苯基)芴基，9,9-螺芴基。
  4. 根据权利要求3所述的有机电子传输材料，其结构式如下：
    Figure PCTCN2016105147-appb-100002
    Figure PCTCN2016105147-appb-100003
    Figure PCTCN2016105147-appb-100004
  5. 根据权利要求4所述的有机电子传输材料，其中R为甲基。
  6. 根据权利要求5所述的有机电子传输材料，其中Ar1、Ar2相同。
  7. 根据权利要求6所述的有机电子传输材料，其中R为甲基；Ar1、Ar2表示为苯基，其结构式如下
    Figure PCTCN2016105147-appb-100005
  8. 权利要求1-7任一所述的有机电子传输材料在仅电子有机半导体二极管器件中的应用。
PCT/CN2016/105147 2015-11-10 2016-11-09 有机电子传输材料 WO2017080445A1 (zh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN201510760404.5 2015-11-10
CN201510760404 2015-11-10

Publications (1)

Publication Number Publication Date
WO2017080445A1 true WO2017080445A1 (zh) 2017-05-18

Family

ID=58392877

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CN2016/105147 WO2017080445A1 (zh) 2015-11-10 2016-11-09 有机电子传输材料

Country Status (3)

Country Link
CN (1) CN106543172B (zh)
TW (1) TWI612047B (zh)
WO (1) WO2017080445A1 (zh)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107586294B (zh) * 2016-07-08 2019-10-18 广东阿格蕾雅光电材料有限公司 高Tg有机电子传输器件
KR102430678B1 (ko) * 2019-03-08 2022-08-09 주식회사 엘지화학 화합물 및 이를 포함하는 유기 발광 소자

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1097981A2 (en) * 1999-11-02 2001-05-09 Sony Corporation Organic electroluminescent device
CN101076904A (zh) * 2004-11-24 2007-11-21 普林斯顿大学理事会 具有菲咯啉激子阻挡层的有机光敏光电器件

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1546477A (zh) * 2003-12-04 2004-11-17 复旦大学 电子传输/空穴阻挡材料及其电致红光器件的制备方法
JP2006131782A (ja) * 2004-11-08 2006-05-25 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、照明装置及び表示装置
JP2006156635A (ja) * 2004-11-29 2006-06-15 Konica Minolta Holdings Inc 有機エレクトロルミネッセンス素子及び表示装置

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1097981A2 (en) * 1999-11-02 2001-05-09 Sony Corporation Organic electroluminescent device
CN101076904A (zh) * 2004-11-24 2007-11-21 普林斯顿大学理事会 具有菲咯啉激子阻挡层的有机光敏光电器件

Also Published As

Publication number Publication date
CN106543172A (zh) 2017-03-29
CN106543172B (zh) 2019-02-26
TWI612047B (zh) 2018-01-21
TW201716407A (zh) 2017-05-16

Similar Documents

Publication Publication Date Title
US20150108449A1 (en) Organic electronic material and organic electroluminescent device
TW201536757A (zh) 用於有機發光元件之化合物及具有該化合物的有機發光元件
KR101831270B1 (ko) 유기전계발광소자
KR20080010186A (ko) 안트라센 유도체, 이를 이용한 유기 전자 소자 및 이 유기전자 소자를 포함하는 전자 장치
JP2011506564A (ja) ナフチル置換されたアントラセン誘導体および有機発光ダイオードにおけるその使用
KR20130121597A (ko) 트리페닐아민을 사용한 정공 수송 물질 및 이를 포함한 유기 전계 발광 소자
Gu et al. Tetrasubstituted adamantane derivatives with arylamine groups: Solution-processable hole-transporting and host materials with high triplet energy and good thermal stability for organic light-emitting devices
KR20130121516A (ko) 신규한 아릴아민을 사용한 정공 수송 물질 및 이를 포함한 유기 전계 발광 소자
KR101950255B1 (ko) 인돌로퀴녹살린 유도체를 포함하는 유기전기소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치
TWI623532B (zh) 有機空穴傳輸材料
WO2017080445A1 (zh) 有机电子传输材料
WO2017080446A1 (zh) 仅电子有机半导体二极管器件
JP2014129347A (ja) テトラフェニレンエチレン系化合物及びそれを含むｏｌｅｄデバイス
TWI643856B (zh) 高Tg有機電子傳輸器件
KR101799033B1 (ko) 적색 인광 호스트 물질 및 이를 이용한 유기전계발광소자
TWI612028B (zh) 有機電子傳輸材料
WO2018006680A1 (zh) 高Tg有机电子传输材料
KR20120038818A (ko) 적색 인광 호스트 물질 및 이를 이용한 유기전계발광소자
TWI612703B (zh) 僅電子有機半導體二極體器件
TWI624091B (zh) 僅空穴有機半導體二極體器件
KR100681026B1 (ko) 전계발광소자 및 전자전달 화합물
Gao et al. A simple bipolar host material based on triphenylamine and pyridine featuring σ-linkage for efficient solution-processed phosphorescent organic light-emitting diodes
WO2018120972A1 (zh) 有机发光二极管器件
KR20120036559A (ko) 적색 인광 호스트 물질 및 이를 이용한 유기전계발광소자
KR101794132B1 (ko) 적색 인광 호스트 물질 및 이를 이용한 유기전계발광소자

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 16863621

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 16863621

Country of ref document: EP

Kind code of ref document: A1