CN110903159A - 一种以邻菲啰啉及衍生物为核心化合物及以该化合物为cpl层制作的oled器件 - Google Patents
一种以邻菲啰啉及衍生物为核心化合物及以该化合物为cpl层制作的oled器件 Download PDFInfo
- Publication number
- CN110903159A CN110903159A CN201911009691.0A CN201911009691A CN110903159A CN 110903159 A CN110903159 A CN 110903159A CN 201911009691 A CN201911009691 A CN 201911009691A CN 110903159 A CN110903159 A CN 110903159A
- Authority
- CN
- China
- Prior art keywords
- layer
- phenanthroline
- derivative
- compound
- cpl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/27—Polycyclic condensed hydrocarbons containing three rings
- C07C15/30—Phenanthrenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/10—Aza-phenanthrenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/36—Benzo-cinnolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- 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
-
- 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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] 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
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/85—Arrangements for extracting light from the devices
-
- 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
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- 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
- H10K85/615—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
-
- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- 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
-
- C—CHEMISTRY; METALLURGY
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
Abstract
本发明公开了一种以邻菲啰啉及衍生物为核心化合物及以该化合物为CPL层制作的OLED器件，有机化合物结构如下通式(1)所示：
本发明化合物具有较高的玻璃化温度和分子热稳定性；在可见光领域吸收低、折射率高，在应用于OLED器件的CPL层后，可有效提升OLED器件的光取出效率。本发明材料在OLED器件中应用在CPL层，不参与器件的电子和空穴传输，但对材料的热稳定性、膜结晶性及折射率具有非常高的要求。如上分析，高的Tg温度，保证了材料在薄膜状态下不结晶；低的蒸镀温度，是材料可应用于量产的前提；高的折射率则是本发明材料能应用于CPL层的最主要因素。
Description
技术领域
本发明涉及OLED器件领域，具体为一种以邻菲啰啉及衍生物为核心化合物及以该化合物为CPL层制作的OLED器件。
背景技术
OLED的发光属于电激发光(eletro luminescence EL),由于在应用上的重要性，电激发光现象一直是令人感兴趣的一门科学，有机发光现象最早是1963年由pope教授所发现的，当时他将数百伏的偏压施加于蒽(anthracene)晶体上，观察到发光现象，这是最早的文献报道。由于过高的电压与不佳的发光效率，该现象一直未受到重视。一直到哦1987年，美国柯达公司的邓青云博士(ching W.Tang)以及Steve发布以真空蒸镀的方式制成了多层式的OLED器件，可是空穴与电子局限在电子传输层与空穴传输层的界面附件在结合，大幅度提高了器件的性能，其工作电压与高亮度的商业应用潜力吸引了全球的目光，从此开启了OLED风起云涌的时代。由于小分子材料发明的比较早，而且最早应用于OLED平板显示器上，所以目前OLED多数是指有机小分子OLED。
目前，OLED已经成功应用于显示领域如智能穿戴手机平板进一步还将向大尺寸的电视领域发展，但是内量子效率转化到外量子的过程有极大地光损耗，大约只有20％-30％的内量子效率可以成功转化为外量子效率，严重制约了OLED如何提高OLED的光提取率成为了近年来科学领域研究的热点。针对这个课题，本文在OLED顶发光器件阴极层蒸镀一层CPL层，即光提取层，根据光学折射原理，折射率越高，光提出效率越高，因而可以大幅提高OLED发光效率。
发明内容
本发明的目的在于提供一种以邻菲啰啉及衍生物为核心化合物，化合物结构如下通式(1)所示：
优选的，通式(1)中，X、Y各自独立地表示C或N；且X＝Y。
优选的，通式(1)中每一个Z独立地表示C或N。
优选的，通式(1)中，所述Ar表示为单键、C1-10直链或支链烷基、卤素原、氕原子、氘原子、或氚原子取代或未取代的亚苯基；亚萘基；亚二联苯基；亚三联苯基；芴基；亚呋喃基；亚吡啶基；或亚咔唑基中的一种。
优选的，所述化合物能够作为OLED器件的电子传输层层、电子传输层、发光层或者覆盖层的构成材料来使用。
优选的，有机化合物的具体结构式为：
本发明还提供了一种权利要求1所述的以邻菲啰啉及衍生物为核心化合物为CPL层制作的OLED器，所述OLED器件包括以邻菲啰啉及其衍生物为核心的有机化合物制成的CPL层，以及阴极、电子注入层、电子传输层、空穴阻挡层、发光层、空穴传输层、空穴注入层和Ag/ITO/Ag层。
优选的，OLED器件的制作步骤如下：
a.清洗透明的OLED顶发光玻璃基板分别用去离子水、丙酮、异丙醇超声清洗15min，80℃烘干1h，投入蒸镀腔，等离子处理阳极表面；
b.在阳极表面通过热蒸镀的方式蒸镀空穴注入层材料HT1:NDP-9；
c.通过热蒸镀的方式蒸镀HT1，该层为空穴传输层；
d.在空穴传输层表面蒸镀R Prime1，该层为发光层和空穴传输层的buffer层；
e.通过热蒸镀的方式蒸镀RH1和RD1，该层为发光层；
f.在发光层表面蒸镀HBL1，该层为空穴传输层；
g.在HBL1层表面蒸镀ETL1和LiQ，该层为ETL层；
h.在HBL层表面以热蒸镀方式蒸镀Ag、Mg该层为阴极；
i.在阴极表面蒸镀一层CPL参照物，该层主要提高光提取率。
与现有技术相比，本发明的有益效果是：本发明化合物具有较高的玻璃化温度和分子热稳定性；在可见光领域吸收低、折射率高，在应用于OLED器件的CPL层后，可有效提升OLED器件的光取出效率。本发明材料在OLED器件中应用在CPL层，不参与器件的电子和空穴传输，但对材料的热稳定性、膜结晶性及折射率具有非常高的要求。如上分析，高的Tg温度，保证了材料在薄膜状态下不结晶；低的蒸镀温度，是材料可应用于量产的前提；高的折射率则是本发明材料能应用于CPL层的最主要因素。
附图说明
图1为用本发明的化合物为CPL层制作的OLED器件结构示意图。
具体实施方式
为了使本发明的目的、技术方案及优点更加清楚明白，以下结合具体实施例，对本发明进行进一步详细说明。应当理解，此处所描述的具体实施例仅仅用以解释本发明，并不用于限定本发明。
实施例1
化合物H7的合成
3,5二溴-1-(4-溴联苯基)三联苯(0.1mol)，4-(9-邻菲啰啉)苯硼酸(0.05mol)加入到3L三口瓶中，加入碳酸钾(0.075mol)，甲苯(1L)，乙醇(500mL)，去离子水(500mL)，充分搅拌，氮气保护，加入四三苯基膦钯(5mmol)，缓慢升温至回流110℃，保温24h，TLC检测原料反应完全，降温至室温，静置分层，有机相饱和食盐水洗涤3次，无水硫酸钠干燥，浓缩至半干，加入乙醇，有大量固体产出，真空抽滤，固体真空干燥得化合物H7。HPLC 99.2％，收率78％。MS(EI)m/z:[M]+calcd for C54H34N4,738.87；found,738.28.Anal.Calcd forC54H34N4:C 87.78,H 4.64，N 7.58；found:C 87.75,H 4.86,N 7.39。
实施例2
化合物H12的合成
3,5二溴-1-(4-溴联苯基)三联苯(0.1mol)，4-(9-(1,4二氮杂)菲)苯硼酸(0.05mol)加入到3L三口瓶中，加入碳酸钾(0.075mol)，甲苯(1L)，乙醇(500mL)，去离子水(500mL)，充分搅拌，氮气保护，加入四三苯基膦钯(5mmol)，缓慢升温至回流110℃，保温24h，TLC检测原料反应完全，降温至室温，静置分层，有机相饱和食盐水洗涤3次，无水硫酸钠干燥，浓缩至半干，加入乙醇，有大量固体产出，真空抽滤，固体真空干燥得化合物H12。HPLC 99.5％，收率64％。MS(EI)m/z:[M]+calcd for C54H34N4,738.87；found,738.28.Anal.Calcd for C54H34N4:C 87.78,H 4.64，N 7.58；found:C 87.75,H 4.86,N7.39。
实施例3
化合物H28的合成
2,6二溴-4-(4-溴联苯基)吡啶(0.1mol)，4-(9-邻菲啰啉)苯硼酸(0.05mol)加入到3L三口瓶中，加入碳酸钾(0.075mol)，甲苯(1L)，乙醇(500mL)，去离子水(500mL)，充分搅拌，氮气保护，加入四三苯基膦钯(5mmol)，缓慢升温至回流110℃，保温24h，TLC检测原料反应完全，降温至室温，静置分层，有机相饱和食盐水洗涤3次，无水硫酸钠干燥，浓缩至半干，加入乙醇，有大量固体产出，真空抽滤，固体真空干燥得化合物H28。HPLC 99.5％，收率90％。MS(EI)m/z:[M]+calcd for C53H33N5,739.86；found,739.27.Anal.Calcd forC53H33N5:C 86.04,H 4.50，N 9.47；found:C 86.26,H 4.36,N 9.39。
这些化合物的纯化是通过利用柱色谱法的精制、利用硅胶、活性炭、活性白土等的吸附精制、利用溶剂的重结晶、晶析法等来进行，最终，通过升华精制等进行精制。对于材料的物理特性，本发明对升华后的材料进行玻璃化转变温度(Tg)和折射率的测定。玻璃化转变温度(Tg)成为薄膜状态的稳定性的指标，折射率是光提取率的重要的指标。就玻璃化转变温度(Tg)而言，本文使用高灵敏度差示扫描量热计进行测定。就折射率和消光系数而言，在硅基板上制作50nm的薄膜，使用椭偏仪进行量测。并且通过和市场通过的CPL参照物相比较，本文设计的CPL材料具有相对较高的玻璃化转变温度和相对较高的折射率。
测得的化合物的玻璃化温度和折射率如表1所示：
表1
这样，本发明的化合物与化合物CPL参照物相比折射率在R、G、B发光区域均有所提高，这意味着能够期待有机OLED器件中的光的取出效率的提高。
化合物能够作为OLED器件的电子传输层层、电子传输层、发光层或者覆盖层的构成材料来使用，对OLED器件有着巨大的改善，图1为OLED器件的结构示意图，通过热蒸镀的方式制备了四个红色顶发光器件(CPL参照物/化合物H7/化合物H12化合物H28)各个具体的器件结构如下：
器件实施例1：一种OLED器件，其制备步骤包括：
a.清洗透明的OLED顶发光玻璃基板分别用去离子水、丙酮、异丙醇超声清洗15min，80℃烘干1h，投入蒸镀腔，等离子处理阳极表面；
b.在阳极表面通过热蒸镀的方式蒸镀空穴注入层材料HT1:NDP-9(10nm：0.3)；
c.通过热蒸镀的方式蒸镀HT1(1200nm),该层为空穴传输层；
d.在空穴传输层表面蒸镀R Prime1(800nm)，该层为发光层和空穴传输层的buffer层；
e.通过热蒸镀的方式蒸镀RH1和RD1(40nm:0.3)，该层为发光层；
f.在发光层表面蒸镀HBL1(5nm)，该层为空穴传输层；
g.在HBL1层表面蒸镀ETL1和LiQ(15nm:15),该层为ETL层；
h.在HBL层表面以热蒸镀方式蒸镀Ag、Mg(12nm:1.2)该层为阴极；
i.在阴极表面蒸镀一层CPL参照物(85nm)，该层主要提高光提取率。
按照上述步骤完成电致发光器件后，测量器件的电流效率和寿命，器件的电流-亮度-电压特性是由带有校正过的硅光电二极管的Keithley源测量系统(Keithley2400Sourcemeter、Keithley 2000Currentmeter)完成的。相关的分子结构如下所示：
器件实施例2：光提取层为化合物H7；器件实施例3：光提取层为化合物H12；器件实施例4：光提取层为化合物H28；
所得电致发光器件的检测数据见表2
以上所述，仅为本发明较佳的具体实施方式，但本发明的保护范围并不局限于此，任何熟悉本技术领域的技术人员在本发明揭露的技术范围内，根据本发明的技术方案及其发明构思加以等同替换或改变，都应涵盖在本发明的保护范围之内。
Claims (8)
1.一种以邻菲啰啉及衍生物为核心化合物，其特征在于：有机化合物结构如下通式(1)所示：
2.根据权利要求1所述的一种以邻菲啰啉及衍生物为核心化合物，其特征在于：通式(1)中，X、Y各自独立地表示C或N；且X＝Y。
3.根据权利要求1所述的一种以邻菲啰啉及衍生物为核心化合物，其特征在于：通式(1)中每一个Z独立地表示C或N。
4.根据权利要求1所述的一种以邻菲啰啉及衍生物为核心化合物，其特征在于：通式(1)中，所述Ar表示为单键、C1-10直链或支链烷基、卤素原、氕原子、氘原子、或氚原子取代或未取代的亚苯基；亚萘基；亚二联苯基；亚三联苯基；芴基；亚呋喃基；亚吡啶基；或亚咔唑基中的一种。
5.根据权利要求1所述的一种以邻菲啰啉及衍生物为核心化合物，其特征在于：所述化合物能够作为OLED器件的电子传输层层、电子传输层、发光层或者覆盖层的构成材料来使用。
6.根据权利要求1所述的一种以邻菲啰啉及衍生物为核心化合物，其特征在于：化合物的具体结构式为：
7.一种根据权利要求1所述的以邻菲啰啉及衍生物为核心的化合物为CPL层制作的OLED器件，其特征在于：所述OLED器件包括以邻菲啰啉及其衍生物为核心的有机化合物制成的CPL层，以及阴极、电子注入层、电子传输层、空穴阻挡层、发光层、空穴传输层、空穴注入层和Ag/ITO/Ag层。
8.根据权利要求7所述的一种以邻菲啰啉及衍生物为核心的化合物为CPL层制作的OLED器件，其特征在于：OLED器件的制作步骤如下：
a.清洗透明的OLED顶发光玻璃基板分别用去离子水、丙酮、异丙醇超声清洗15min，80℃烘干1h，投入蒸镀腔，等离子处理阳极表面；
b.在阳极表面通过热蒸镀的方式蒸镀空穴注入层材料HT1:NDP-9；
c.通过热蒸镀的方式蒸镀HT1，该层为空穴传输层；
d.在空穴传输层表面蒸镀R Prime1，该层为发光层和空穴传输层的buffer层；
e.通过热蒸镀的方式蒸镀RH1和RD1，该层为发光层；
f.在发光层表面蒸镀HBL1，该层为空穴传输层；
g.在HBL1层表面蒸镀ETL1和LiQ，该层为ETL层；
h.在HBL层表面以热蒸镀方式蒸镀Ag、Mg该层为阴极；
i.在阴极表面蒸镀一层CPL参照物，该层主要提高光提取率。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910740849 | 2019-08-12 | ||
| CN2019107408495 | 2019-08-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN110903159A true CN110903159A (zh) | 2020-03-24 |
Family
ID=69814857
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911009691.0A Pending CN110903159A (zh) | 2019-08-12 | 2019-10-23 | 一种以邻菲啰啉及衍生物为核心化合物及以该化合物为cpl层制作的oled器件 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110903159A (zh) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113418930A (zh) * | 2021-06-04 | 2021-09-21 | 西北工业大学 | 一种用于快速检测铁板表面镀层是否完整的方法 |
| CN113444112A (zh) * | 2021-06-25 | 2021-09-28 | 上海钥熠电子科技有限公司 | 杂环化合物及其在有机电致发光器件中的应用 |
| CN113651836A (zh) * | 2021-08-18 | 2021-11-16 | 清华大学 | 一种有机化合物及包含该化合物的有机电致发光器件 |
| CN113418930B (zh) * | 2021-06-04 | 2024-05-10 | 西北工业大学 | 一种用于快速检测铁板表面镀层是否完整的方法 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003045662A (ja) * | 2001-08-01 | 2003-02-14 | Konica Corp | 有機エレクトロルミネッセンス素子及び表示装置 |
| CN106946853A (zh) * | 2017-05-11 | 2017-07-14 | 江苏三月光电科技有限公司 | 一种基于三嗪和苯并咪唑的有机化合物及其在有机电致发光器件上的应用 |
| KR20170111802A (ko) * | 2016-03-29 | 2017-10-12 | 주식회사 엘지화학 | 유기 발광 소자 |
| CN109384802A (zh) * | 2017-08-08 | 2019-02-26 | 三星显示有限公司 | 杂环化合物以及包括该杂环化合物的有机发光装置和电子设备 |
-
2019
- 2019-10-23 CN CN201911009691.0A patent/CN110903159A/zh active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003045662A (ja) * | 2001-08-01 | 2003-02-14 | Konica Corp | 有機エレクトロルミネッセンス素子及び表示装置 |
| KR20170111802A (ko) * | 2016-03-29 | 2017-10-12 | 주식회사 엘지화학 | 유기 발광 소자 |
| CN106946853A (zh) * | 2017-05-11 | 2017-07-14 | 江苏三月光电科技有限公司 | 一种基于三嗪和苯并咪唑的有机化合物及其在有机电致发光器件上的应用 |
| CN109384802A (zh) * | 2017-08-08 | 2019-02-26 | 三星显示有限公司 | 杂环化合物以及包括该杂环化合物的有机发光装置和电子设备 |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113418930A (zh) * | 2021-06-04 | 2021-09-21 | 西北工业大学 | 一种用于快速检测铁板表面镀层是否完整的方法 |
| CN113418930B (zh) * | 2021-06-04 | 2024-05-10 | 西北工业大学 | 一种用于快速检测铁板表面镀层是否完整的方法 |
| CN113444112A (zh) * | 2021-06-25 | 2021-09-28 | 上海钥熠电子科技有限公司 | 杂环化合物及其在有机电致发光器件中的应用 |
| CN113651836A (zh) * | 2021-08-18 | 2021-11-16 | 清华大学 | 一种有机化合物及包含该化合物的有机电致发光器件 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109761967B (zh) | 一种基于杂芳基胺类结构的有机化合物及其在oled上的应用 | |
| CN109824659B (zh) | 一种基于杂芳基胺类结构的有机化合物及其应用 | |
| CN109449304B (zh) | 一种基于三嗪和苯并咪唑的有机化合物及其在有机电致发光器件上的应用 | |
| KR20180128417A (ko) | 일종의 트리아진과 벤조이미다졸을 핵심으로 하는 유기화합물 및 유기 전계 발광소자 상의 관련 응용 | |
| CN109206420B (zh) | 一种基于三嗪的有机化合物及其在有机电致发光器件上的应用 | |
| CN110229145B (zh) | 一种基于氮杂苯的有机化合物及其在oled上的应用 | |
| CN107417668B (zh) | 一种基于氮杂苯和苯并咪唑的有机化合物及其在oled上的应用 | |
| CN111253332A (zh) | 一种有机化合物及其制备方法和在oled上的应用 | |
| CN109928886B (zh) | 一种含有三芳胺和芴的化合物及其应用 | |
| CN110964021A (zh) | 一种以芴为核心的化合物、制备方法及其应用 | |
| CN113264911A (zh) | 一种化合物、有机发光材料和有机电致发光器件 | |
| CN109232376A (zh) | 一种芴衍生物及其有机电致发光器件 | |
| CN111303149B (zh) | 一种苯并五元环并稠杂环类有机化合物及其应用 | |
| CN113929709A (zh) | 一种含硼氮有机化合物及包含其的有机电致发光器件 | |
| CN110903159A (zh) | 一种以邻菲啰啉及衍生物为核心化合物及以该化合物为cpl层制作的oled器件 | |
| CN106543071B (zh) | 一种以二苯并庚烯酮为核心的化合物及其在oled上的应用 | |
| CN113937233B (zh) | 一种有机电致发光器件及其应用 | |
| CN110577523B (zh) | 一种含三芳胺结构的化合物及其制备的有机电致发光器件 | |
| CN112479904B (zh) | 一种以茚并蒽衍生物为核心的有机化合物及其应用 | |
| CN111253382B (zh) | 一种以酮类衍生物为核心的有机化合物及其制备方法和其应用 | |
| CN116332773B (zh) | 一种发光辅助材料及其制备方法和应用 | |
| CN110845508A (zh) | 一种以螺芴蒽酮为核心的化合物、制备方法及其应用 | |
| CN112479901B (zh) | 一种以茚并蒽衍生物为核心的有机化合物及其应用 | |
| CN112159326A (zh) | 一种化合物、发光层染料材料和有机电致发光器件 | |
| CN109574989B (zh) | 一种以二苯并六元环为核心的化合物及其在有机电致发光器件上的应用 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20200324 |
|
| RJ01 | Rejection of invention patent application after publication |