CN110183333B - 一种有机电致发光材料及包含该材料的有机电致发光器件 - Google Patents
一种有机电致发光材料及包含该材料的有机电致发光器件 Download PDFInfo
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- CN110183333B CN110183333B CN201910532443.8A CN201910532443A CN110183333B CN 110183333 B CN110183333 B CN 110183333B CN 201910532443 A CN201910532443 A CN 201910532443A CN 110183333 B CN110183333 B CN 110183333B
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- 239000007924 injection Substances 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 239000012044 organic layer Substances 0.000 claims description 10
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 5
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- 125000003828 azulenyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
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- HSIYJKUTMUOWPE-UHFFFAOYSA-N dibenzothiophen-3-amine Chemical compound C1=CC=C2C3=CC=C(N)C=C3SC2=C1 HSIYJKUTMUOWPE-UHFFFAOYSA-N 0.000 description 1
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
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- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
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- DZRDATNLTUIPAY-UHFFFAOYSA-N n,9-diphenylcarbazol-3-amine Chemical compound C=1C=C2N(C=3C=CC=CC=3)C3=CC=CC=C3C2=CC=1NC1=CC=CC=C1 DZRDATNLTUIPAY-UHFFFAOYSA-N 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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Classifications
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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Abstract
本发明提供一种有机电致发光材料及包含所述有机电致发光材料的有机发光器件,该有机电致发光材料的结构式为:
Description
技术领域
本发明涉及有机电致发光技术领域,具体涉及一种有机电致发光材料及包含该材料的有机电致发光器件。
背景技术
近年来,有机电致发光器件(OLED,Organic electroluminescent device)作为新一代显示技术逐渐进入人们的视野。常见的有机电致发光器件是由阳极、阴极以及在阴极和阳极之间设置一层以上的有机层构成。当阴阳两极施加电压时,两电极产生电场,在电场的作用下,阴极侧的电子向发光层移动,阳极侧的空穴也向发光层移动,两者在发光层结合形成激子,激子处于激发态向外释放能量,从激发态释放能量变为基态释放能量的过程对外发光。因此,提高OLED器件中电子和空穴的再结合性是至关重要的。
为了提高有机电致发光器件的亮度、效率和寿命,通常在器件中使用多层结构。这些多层结构包括:空穴注入层(hole injection layer)、空穴传输层(hole transportlayer)、电子阻挡层(electron-bl℃king layer)、发光层(emitting layer)和电子传输层(electron transport layer)等等。这些有机层具有提高载流子(空穴和电子)在各层界面间的注入效率,平衡载流子在各层之间传输的能力,从而提高器件的亮度和效率。
目前常用的空穴传输材料为NPD,NPD虽然具有优异的空穴传输性能,但是玻璃化转变温度(Tg)只有96℃,这导致在高温条件下,有机电致发光器件在高温下容易结晶,从而降低性能。
关于金刚烷(adamantane)衍生物已记录在很多文献中。例如:
专利文献CN201680002336.1涉及金刚烷衍生物及其有机电致放光器件,其包括基板、蒸镀在基板上的阴极、阳极,和蒸镀在阴极和阳极之间的有机层,其中有机层包含空穴传输层,其空穴传输层包含如下结构的金刚烷衍生物。尽管这些性能优良的有机电致发光材料已被陆续开发出来,但都是单胺类结构,单胺结构空穴传输率低,因此其得到的器件效率和寿命仍然有待提高,如何设计新的性能更好的材料进行调节,以使所有器件能够达到降低电压、提高效率和寿命的效果,一直是本领域技术人员亟待解决的问题。
发明内容
本发明的目的在于提供一种性能优异的有机电致发光材料,可用作有机电致发光器件中的空穴传输层、电子阻挡层等等。本发明的另一目的在于提供一种包含所述有机电致发光材料的有机发光器件,具有较低的驱动电压、较高的发光效率和使用寿命。
本发明是通过以下技术方案来实现:
一种有机电致发光材料,该材料的结构式如化学式1所示:
其中,R2、R4和R5相同或不同,分别独立地选自取代或未取代的碳原子数为1-20的烷基、取代或未取代的碳原子数为2-20的烯基、取代或未取代的碳原子数为2-24的炔基、取代或未取代的碳原子数为3-20的环烷基、取代或未取代的碳原子数为2-20的杂环烷基、取代或未取代的碳原子数为7-30的芳烷基、取代或未取代的碳原子数为2-30的杂芳烷基、取代或未取代的碳原子数为6-30的芳基、取代或未取代的碳原子数为1-30的杂芳基;
R1和R3相同或不同,分别独立地选自单键、取代或未取代碳原子数为1-30的芳基、取代或未取代的碳原子数为1-30杂芳基、取代或未取代的碳原子数为7-30的芳烷基、取代或未取代的碳原子数为2-30的杂芳烷基;
所述R1、R2、R3、R4和R5的取代基相同或不同,分别独立地选自氘、氰基、硝基、卤素、羟基、碳原子数为1-40的烷基基团、碳原子数3-40的环烷基基团、碳原子数2-40的烯基基团、碳原子数2-40的炔基基团、碳原子数2-40的杂环烷基基团、碳原子数7-40的芳烷基基团、碳原子数2-40的杂芳烷基基团、碳原子数6-40的芳基基团、碳原子数1-40的杂芳基基团、碳原子数1-40的烷氧基基团、碳原子数1-40的烷氨基基团、碳原子数6-40的芳氨基基团、碳原子数为1-40的烷硫基基团、碳原子数7-40的芳烷氨基基团、碳原子数1-24的杂芳氨基基团、碳原子数为1-45的烷基甲硅烷基基团、碳原子数为6-50的芳基甲硅烷基基团、碳原子数为6-30的芳氧基基团、碳原子数为6-30芳硫基基团。
优选的,R2、R4和R5相同或不同,分别独立地选自取代或未取代的碳原子数为7-30的芳烷基、取代或未取代的碳原子数为2-30的杂芳烷基、取代或未取代的碳原子数为6-30的芳基、取代或未取代的碳原子数为1-30的杂芳基。
优选的,R1和R3相同或不同,分别独立地选自单键、取代或未取代的苯基、取代或未取代的联苯基、取代或未取代的三联苯基、取代或未取代的基、取代或未取代的菲基、取代或未取代的萘基、取代或未取代的甘菊环基、取代或未取代的茚基、取代或未取代的吡啶基、取代或未取代的嘧啶基、取代或未取代的三嗪基、取代或未取代的咪唑基。
优选的,所述化学式1为如下结构中的一种,但不仅限于此:
一种有机电致发光器件,包括阴极、阳极以及设置在所述阴极和阳极之间的一层以上的有机层,所述有机层至少有一层包含所述的电致发光材料。
优选的,所述有机层包括空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层以及电子注入层。
优选的,所述空穴传输层包含所述的电致发光材料。
优选的,所述电子阻挡层包含所述的电致发光材料。
与现有技术相比,本发明具有以下有益的技术效果:
相比于含有金刚烷基的单胺类结构,本发明含有的双胺结构有着较高的HOMO能量以及空穴迁移率,可以表现出比单胺类材料器件更高的效率和寿命。由于双胺类材料取代位点较多,通过金刚烷基在不同位置的取代,也可以对材料空间结构和分子堆叠起到更精细的调节作用;尤其是本发明作为电子阻挡层时,可以起到更佳的空穴传输速率调节作用,从而通过平衡空穴和电子传导率,进一步增强器件效率和寿命。此外,双胺结构具有高的空穴传导率,但由于其分子量较小以及对称性高,导致其易于低温下结晶;将双胺结构与金刚烷基相结合,引入了大位阻的金刚烷基后可以大幅度改善此现象,将玻璃态转变温度和结晶温度提高30-50℃,从而有效的抑制了材料的结晶,以及随之引起的发光器件的寿命低下的问题。
包含所述有机电致发光材料的有机发光器件,具有较低的驱动电压、较高的发光效率和使用寿命。
具体实施方式
下面结合具体的实施例对本发明做进一步的详细说明,所述是对本发明的解释而不是限定。
一种有机电致发光材料,该材料的结构式如化学式1所示:
其中,R2、R4和R5相同或不同,分别独立地选自取代或未取代的碳原子数为1-20的烷基、取代或未取代的碳原子数为2-20的烯基、取代或未取代的碳原子数为2-24的炔基、取代或未取代的碳原子数为3-20的环烷基、取代或未取代的碳原子数为2-20的杂环烷基、取代或未取代的碳原子数为7-30的芳烷基、取代或未取代的碳原子数为2-30的杂芳烷基、取代或未取代的碳原子数为6-30的芳基、取代或未取代的碳原子数为1-30的杂芳基;
R1和R3相同或不同,分别独立地选自单键、取代或未取代碳原子数为1-30的亚芳基、取代或未取代的碳原子数为1-30亚杂芳基、取代或未取代的碳原子数为7-30的芳烷基、取代或未取代的碳原子数为2-30的杂芳烷基;
所述R1、R2、R3、R4和R5的取代基相同或不同,分别独立地选自氘、氰基、硝基、卤素、羟基、碳原子数为1-40的烷基基团、碳原子数3-40的环烷基基团、碳原子数2-40的烯基基团、碳原子数2-40的炔基基团、碳原子数2-40的杂环烷基基团、碳原子数7-40的芳烷基基团、碳原子数2-40的杂芳烷基基团、碳原子数6-40的芳基基团、碳原子数1-40的杂芳基基团、碳原子数1-40的烷氧基基团、碳原子数1-40的烷氨基基团、碳原子数6-40的芳氨基基团、碳原子数为1-40的烷硫基基团、碳原子数7-40的芳烷氨基基团、碳原子数1-24的杂芳氨基基团、碳原子数为1-45的烷基甲硅烷基基团、碳原子数为6-50的芳基甲硅烷基基团、碳原子数为6-30的芳氧基基团、碳原子数为6-30芳硫基基团。
本发明中的未取代烷基,指的是碳原子数为1-20的直链的烷基,或包含碳原子数为1-13的支链的烷基。例如,甲基、乙基、丙基、异丁基、仲丁基、戊基、异戊基、已基等。取代的碳原子数为1-20的烷基是指至少一个氢原子被氘原子、F、Cl、I、CN、羟基、硝基、氨基等取代。
本发明中的未取代的烯基,指的是的碳原子数为2-20的烯基,包含碳碳双键的碳原子数为2-20的直链的烯基,或包含碳原子数为1-13的支链的烯基。例如:乙烯基、丙烯基、烯丙基、异丙烯基、2-丁烯基等。取代的碳原子数为2-20的烯基是指至少一个氢原子被氘原子、F、Cl、I、CN、羟基、硝基、氨基等取代。
本发明中的未取代的炔基,指的是的碳原子数为2-24的炔基,包含碳碳三键的碳原子数为2-35的直链的炔基,或包含碳原子数为1-10的支链的炔基。例如:乙炔基、2-丙炔基等。取代的碳原子数为2-24的炔基是指至少一个氢原子被氘原子、F、Cl、I、CN、羟基、硝基、氨基等取代。
本发明中的未取代的芳基,指的是的碳原子数为6-30的芳基。例如:苯基、萘基、芘基、二甲基芴基、蒽基、菲基、基、甘菊环基、苊基、联苯基、苯并蒽基、螺二芴基、苝基、茚基等。取代的碳原子数为6-30的芳基是指至少一个氢原子被氘原子、F、Cl、I、CN、羟基、硝基、氨基等取代。
本发明中未取代的芳烷基,指的是碳原子数为7-30的芳烷基。例如:甲苯基、二甲基芴基等等。取代的碳原子数为7-30的芳烷基是指至少一个氢原子被氘原子、F、Cl、I、CN、羟基、硝基、氨基等取代。
本发明中未取代的杂芳基,指的是碳原子数为1-30的杂芳基。例如:吡啶基、吡嗪基、嘧啶基、哒嗪基、三嗪基、喹啉基、吲哚基、咔唑基、二苯并呋喃基、二苯并噻吩基、二苯并硒吩基等。取代的碳原子数为1-30的杂芳基是指至少一个氢原子被氘原子、F、Cl、I、CN、羟基、硝基、氨基等取代。
本发明中未取代的环烷基,指的是碳原子数为3-20的环烷基。例如:环丙基、环丁基、环戊基、环己基、降冰片基、金刚烷基等等。取代的碳原子数为3-20的环烷基是指至少一个氢原子被氘原子、F、Cl、I、CN、羟基、硝基、氨基等取代。
以下,通过实施例对本发明进一步详细说明。但是,下述实施例仅是本发明的例示,而并非限定本发明。
合成例1
化合物1的合成
将1-金刚烷醇(50.0g,328.4mmol)、溴苯(51.6g,328.4mmol)、二氯甲烷(500mL)加入圆底烧瓶中,氮气保护下降温至-5-0℃、下滴加三氟甲磺酸(73.9g,492.6mmol),保温搅拌3h;向反应液中加入去离子水(300mL)水洗至pH=7,加入二氯甲烷(100mL)进行萃取,合并有机相,使用无水硫酸镁进行干燥,过滤,减压除去溶剂;所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯,得到白色固体中间体I-A-1(53.1g,55.4%)。
将中间体I-A-1(7.0g,24.04mmol),苯胺(2.69g,28.84mmol),三(二亚苄基丙酮)二钯(0.22g,0.24mmol),2-二环己基磷-2’,4’,6’-三异丙基联苯(0.23g,0.48mmol)以及叔丁醇钠(3.46g,36.05mmol)加入甲苯(60mL)中,氮气保护下加热至108℃,搅拌3h;而后冷却至室温,反应液使用去离子水洗后加入无水硫酸镁干燥,过滤后将滤液通过短硅胶柱,减压除去溶剂;使用二氯甲烷/正庚烷体系对粗品进行重结晶提纯,得到浅绿色固体中间体I-A(5.83g,79.9%)。
将二苯胺(3.80g,22.45mmol),4-溴-4’-碘联苯(10.48g,29.19mmol),三(二亚苄基丙酮)二钯(0.21g,0.22mmol),三叔丁基膦(0.10g,0.44mmol)以及叔丁醇钠(3.24g,33.68mmol)加入甲苯(100mL)中,氮气保护下加热至108℃,搅拌10h;而后冷却至室温,反应液使用水洗后加入硫酸镁干燥,过滤后将滤液减压除去溶剂;使用正庚烷为流动相进行硅胶柱色谱提纯,得到白色固体中间体II-A(3.6g,40.06%)。
将中间体I-A(3g,9.89mmol),中间体II-A(3.55g,9.89mmol),三(二亚苄基丙酮)二钯(0.09g,0.10mmol),2-二环己基磷-2’,6’-二甲氧基联苯(0.08g,0.20mmol)以及叔丁醇钠(1.43g,14.83mmol)加入甲苯(30mL)中,氮气保护下加热至108℃,搅拌1h;而后冷却至室温,反应液过滤后将滤液减压除去溶剂;使用二氯甲烷/正庚烷(1:1)为流动相进行硅胶柱色谱提纯,之后用二氯甲烷/乙酸乙酯体系对粗品进行重结晶提纯,得到白色固体化合物1(5.15g,83.74%)。质谱:m/z=623.3(M+H)+
合成例2
化合物2的合成
将N-苯基-4-联苯胺(5.00g,20.38mmol),4-溴-4’-碘联苯(9.15g,25.48mmol),三(二亚苄基丙酮)二钯(0.19g,0.20mmol),三叔丁基膦(0.08g,0.41mmol)以及叔丁醇钠(2.94g,30.57mmol)加入甲苯(80mL)中,氮气保护下加热至108℃,搅拌16h;而后冷却至室温,反应液使用水洗后加入硫酸镁干燥,过滤后将滤液减压除去溶剂;使用正庚烷为流动相进行硅胶柱色谱提纯,得到中间体II-B(5.55g,57.16%)。
将上述合成例1中的中间体I-A(4.70g,15.49mmol),中间体II-B(5.55g,15.49mmol),三(二亚苄基丙酮)二钯(0.14g,0.15mmol),2-二环己基磷-2’,6’-二甲氧基联苯(0.13g,0.31mmol)以及叔丁醇钠(2.23g,23.23mmol)加入甲苯(50mL)中,氮气保护下加热至108℃,搅拌1h;而后冷却至室温,反应液过滤后将滤液减压除去溶剂;使用二氯甲烷/正庚烷(1:1)为流动相进行硅胶柱色谱提纯,之后用二氯甲烷/乙酸乙酯体系对粗品进行重结晶提纯,得到白色固体化合物2(7.34g,67.78%)。质谱:m/z=699.4(M+H)+
合成例3
化合物3的合成
将3-溴二苯并呋喃(10.0g,40.47mmol),苯胺(4.15g,44.52mmol),三(二亚苄基丙酮)二钯(0.37g,0.40mmol),2-二环己基磷-2,4,6-三异丙基联苯(0.39g,0.81mmol)以及叔丁醇钠(5.84g,60.71mmol)加入甲苯(100mL)中,氮气保护下加热至108℃,搅拌1h;而后冷却至室温,反应液使用水洗后加入硫酸镁干燥,过滤后将滤液通过短硅胶柱,过柱液减压除去溶剂;使用二氯甲烷/正庚烷体系对粗品进行重结晶提纯,得到灰色固体中间体II-C-1(8.2g,78.17%)。
将3-溴-4’氯-1,1’-联苯(8.00g,29.90mmol),中间体II-C-1(5.17g,19.93mmol),三(二亚苄基丙酮)二钯(0.18g,0.20mmol),三叔丁基膦(0.10g,0.40mmol)以及叔丁醇钠(2.87g,29.90mmol)加入甲苯(70mL)中,氮气保护下加热至108℃,搅拌12h;而后冷却至室温,反应液使用水洗后加入硫酸镁干燥,过滤后将滤液减压除去溶剂;使用正庚烷为流动相进行硅胶柱色谱提纯,得到灰色固体中间体II-C(4.82g,54.28%)。
将上述合成例1中的中间体I-A(3.00g,9.89mmol),中间体II-C(4.41g,9.89mmol),三(二亚苄基丙酮)二钯(0.10g,0.10mmol),2-二环己基磷-2’,6’-二甲氧基联苯(0.09g,0.20mmol)以及叔丁醇钠(1.43g,14.83mmol)加入甲苯(50mL)中,氮气保护下加热至108℃,搅拌2h;而后冷却至室温,反应液过滤后将滤液减压除去溶剂;使用二氯甲烷/正庚烷(1:3)为流动相进行硅胶柱色谱提纯,之后用二氯甲烷/乙酸乙酯体系对粗品进行重结晶提纯,得到白色固体化合物3(5.35g,76.14%)。质谱:m/z=713.3(M+H)+
合成例4
化合物4的合成
将苯胺(10.0g,107.38mmol),3-溴二苯并噻吩(26.91.0g,102.26mmol),三(二亚苄基丙酮)二钯(0.94g,1.02mmol),2-二环己基磷-2,4,6-三异丙基联苯(0.98g,2.05mmol)以及叔丁醇钠(14.74g,153.40mmol)加入甲苯(180mL)中,氮气保护下加热至108℃,搅拌2h;而后冷却至室温,反应液使用水洗后加入硫酸镁干燥,过滤后将滤液通过短硅胶柱,过柱液减压除去溶剂;使用二氯甲烷/正庚烷体系对粗品进行重结晶提纯,得到白色固体中间体II-D-1(21.69g,77.02%)。
将中间体II-D-1(5.90g,21.43mmol),4-溴-4’-碘联苯(10g,27.85mmol),三(二亚苄基丙酮)二钯(0.19g,0.21mmol),三叔丁基膦(0.20g,0.13mmol)以及叔丁醇钠(3.09g,32.14mmol)加入甲苯(80mL)中,氮气保护下加热至108℃,搅拌7h;而后冷却至室温,反应液过滤后将滤液减压除去溶剂;使用正庚烷为流动相进行硅胶柱色谱提纯,之后用二氯甲烷/正庚烷体系对粗品进行重结晶提纯,得到白色固体中间体II-D(6.07g,55.95%)。
将上述合成例1中的中间体I-A(3.60g,11.86mmol),中间体II-D(6.07g,11.86mmol),三(二亚苄基丙酮)二钯(0.11g,0.12mmol),2-二环己基磷-2’,6’-二甲氧基联苯(0.11g,0.24mmol)以及叔丁醇钠(1.71g,17.80mmol)加入甲苯(50mL)中,氮气保护下加热至108℃,搅拌1h;而后冷却至室温,反应液过滤后将滤液减压除去溶剂;使用二氯甲烷/正庚烷体系对粗品进行重结晶提纯,得到白色固体化合物4(7.12g,56.62%)。质谱:m/z=729.3(M+H)+
合成例5
化合物5的合成
将1-金刚烷醇(10.0g,65.69mmol)、4-溴联苯(15.31g,65.69mmol)、加入盛有(150mL)二氯甲烷的圆底烧瓶中,氮气保护下降温至(-20)-(-10)℃下滴加三氟甲磺酸(14.7g,98.53mmol),保温搅拌6h;向反应液中加入去离子水(100mL)水洗至pH=7,加入MC(100mL)进行萃取,合并有机相,使用无水硫酸镁进行干燥,过滤,减压除去溶剂;所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯,得到白色固体中间体I-E-1(9.80g,40.61%)。
将中间体I-E-1(9.50g,25.89mmol),4-氨基联苯(4.60g,27.18mmol),三(二亚苄基丙酮)二钯(0.24g,0.26mmol),2-二环己基磷-2’,4’,6’-三异丙基联苯(0.25g,0.52mmol)以及叔丁醇钠(3.73g,38.83mmol)加入甲苯(100mL)中,氮气保护下加热至108℃,搅拌3h;而后冷却至室温,反应液使用去离子水洗后加入无水硫酸镁干燥,过滤后将滤液通过短硅胶柱,减压除去溶剂;使用二氯甲烷/正庚烷体系对粗品进行重结晶提纯,得到浅绿色固体中间体I-E(8.71g,73.88%)。
将2-溴,4-氯联苯(50.00g,180.69mmol)、苯硼酸(20.17g,170.79mmol)、四三苯基膦钯(4.1g,0.36mmol)、碳酸钾(54.0g,390.16mmol)、四丁基氯化铵(.9.9g,35.6mmol)、甲苯(400mL)、乙醇(100mL)和去离子水(100mL)加入圆底烧瓶中,氮气保护下升温至78℃,搅拌8小时;将反应液冷却至室温,加入甲苯(1000mL)进行萃取,合并有机相,使用无水硫酸镁进行干燥,过滤,减压除去溶剂;所得粗品使用二氯甲烷/正庚烷(1:8)为流动相进行硅胶柱色谱提纯,之后用二氯甲烷/乙醇体系进行重结晶提纯,得到浅黄色固体中间体II-E-1(38.0g,80.85%)。
将中间体II-E-1(3.80g,14.35mmol),4-氨基联苯(2.55g,15.07mmol),三(二亚苄基丙酮)二钯(0.29g,0.31mmol),2-二环己基磷-2’,4’,6’-三异丙基联苯(0.26g,0.63mmol)以及叔丁醇钠(2.26g,23.5mmol)加入甲苯(30mL)中,氮气保护下加热至108℃,搅拌5h;而后冷却至室温,反应液使用去离子水洗后加入无水硫酸镁干燥,过滤后将滤液通过短硅胶柱,减压除去溶剂;使用二氯乙烷对粗品进行重结晶提纯,得到浅绿色片状固体中间体II-E-2(4.7g,82.31%)。
将II-E-2(4.50g,11.14mmol),4-溴-4’-碘联苯(6.00g,16.7mmol),三(二亚苄基丙酮)二钯(0.10g,0.11mmol),三叔丁基磷(0.05g,0.22mmol)以及叔丁醇钠(1.61g,16.71mmol)加入甲苯(50mL)中,氮气保护下加热至108℃,搅拌16h;而后冷却至室温,反应液使用水洗后加入硫酸镁干燥,过滤后将滤液减压除去溶剂;使用正庚烷为流动相进行硅胶柱色谱提纯,得到白色中间体II-E(3.2g,45.71%)。
将中间体I-E(2.30g,5.05mmol),中间体II-E(3.2g,5.05mmol),三(二亚苄基丙酮)二钯(0.10g,0.11mmol),2-二环己基磷-2’,6’-二甲氧基联苯(0.08g,0.22mmol)以及叔丁醇钠(0.73g,7.58mmol)加入甲苯(30mL)中,氮气保护下加热至108℃,搅拌2h;而后冷却至室温,反应液过滤后将滤液减压除去溶剂;使用二氯甲烷/正庚烷(1:1)为流动相进行硅胶柱色谱提纯,之后用二氯甲烷/正庚烷体系对粗品进行重结晶提纯,得到白色固体化合物5(2.12g,41.9%)。质谱:m/z=1003.5(M+H)+
合成例6
化合物6的合成
将3-溴-N,N-双(4-甲基苯基)苯胺(10.0g,30.74mmol)、4'-溴-4-联苯硼酸(5.68g,20.50mmol)、四三苯基膦钯(0.47g,0.41mmol)、碳酸钾(6.22g,45.09mmol)、四丁基氯化铵(1.14g,4.10mmol)、甲苯(80mL)、乙醇(20mL)和去离子水(20mL)加入圆底烧瓶中,氮气保护下升温至78℃,搅拌8小时;将反应液冷却至室温,加入甲苯(100mL)进行萃取,合并有机相,使用无水硫酸镁进行干燥,过滤,减压除去溶剂;所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯,之后用二氯甲烷/乙酸乙酯体系进行重结晶提纯,得到白色固体中间体II-F(3.69g,35.69%)。
将上述合成例4中的中间体I-D(3.50g,7.68mmol),中间体II-F(3.8g,7.68mmol),三(二亚苄基丙酮)二钯(0.14g,0.15mmol),2-二环己基磷-2’,6’-二甲氧基联苯(0.13g,0.31mmol)以及叔丁醇钠(1.11g,11.52mmol)加入甲苯(30mL)中,氮气保护下加热至108℃,搅拌3h;而后冷却至室温,反应液过滤后将滤液减压除去溶剂;使用二氯甲烷/正庚烷体系对粗品进行重结晶提纯,得到白色固体化合物6(4.17g,61.33%)。质谱:m/z=879.5(M+H)+
合成例7
化合物7的合成
将1-金刚烷醇(10.0g,65.69mmol)、1-溴代萘(12.95g,62.56mmol)、二氯甲烷(120mL)加入圆底烧瓶中,氮气保护下降温至(-20)-(-10)℃、下滴加三氟甲磺酸(14.08g,93.84mmol),保温搅拌6h;向反应液中加入去离子水(300mL)水洗至pH=7,加入MC(50mL)进行萃取,合并有机相,使用无水硫酸镁进行干燥,过滤后滤液减压除去溶剂;所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯,得到白色固体中间体I-G-1(12.58g,58.92%)。
将中间体I-G-1(10g,29.30mmol),苯胺(2.87g,30.77mmol),三(二亚苄基丙酮)二钯(0.27g,0.29mmol),2-二环己基磷-2’,4’,6’-三异丙基联苯(0.28g,0.59mmol)以及叔丁醇钠(4.22g,43.95mmol)加入甲苯(80mL)中,氮气保护下加热至108℃,搅拌3h;而后冷却至室温,反应液使用去离子水洗后加入无水硫酸镁干燥,过滤后将滤液通过短硅胶柱,减压除去溶剂;使用二氯甲烷/正庚烷体系对粗品进行重结晶提纯,得到橙色固体中间体I-G(7.63g,73.65%)。
将苯胺(3.00g,32.69mmol),9-(4-溴苯基)-咔唑(10.00g,31.13mmol),三(二亚苄基丙酮)二钯(0.29g,0.31mmol),2-二环己基磷-2’,4’,6’-三异丙基联苯(0.29g,0.63mmol)以及叔丁醇钠(4.49g,46.70mmol)加入甲苯(80mL)中,氮气保护下加热至108℃,搅拌6h;而后冷却至室温,反应液使用去离子水洗后加入无水硫酸镁干燥,过滤后将滤液通过短硅胶柱,减压除去溶剂;使用二氯甲烷/正庚烷(1:3)为流动相进行硅胶柱色谱提纯,之后用二氯甲烷/正庚烷体系对粗品进行重结晶提纯,得到白色固体中间体II-G-1(8.54g,82.05%)。
将中间体II-G-1(5.00g,14.95mmol),4-溴-4’-碘联苯(8.05g,22.43mmol),三(二亚苄基丙酮)二钯(0.14g,0.15mmol),2-二环己基磷-2’,6’-二甲氧基联苯(0.14g,0.30mmol)以及叔丁醇钠(2.16g,22.43mmol)加入甲苯(80mL)中,氮气保护下加热至108℃,搅拌16h;而后冷却至室温,反应液过滤后将滤液减压除去溶剂;所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯,之后用正庚烷对粗品进行重结晶提纯,得到黄色固体中间体II-G(3.52g,41.61%)。
将中间体I-G(2.20g,6.22mmol),中间体II-G(3.52g,6.22mmol),三(二亚苄基丙酮)二钯(0.06g,0.06mmol),2-二环己基磷-2’,6’-二甲氧基联苯(0.05g,0.12mmol)以及叔丁醇钠(0.90g,9.34mmol)加入甲苯(30mL)中,氮气保护下加热至108℃,搅拌2h;而后冷却至室温,反应液过滤后将滤液减压除去溶剂;使用二氯甲烷/乙酸乙酯体系对粗品进行重结晶提纯,得到白色固体化合物7(2.31g,44.25%)。质谱:m/z=838.4(M+H)+
合成例8
化合物8的合成
将1-金刚烷醇(10.0g,65.69mmol)、邻溴甲苯(11.23g,65.69mmol)、二氯甲烷(120mL)加入圆底烧瓶中,氮气保护下降温至(-45)-(-35)℃℃下滴加三氟甲磺酸(14.78g,98.53mmol),保温搅拌5h;向反应液中加入去离子水(300mL)水洗至pH=7,加入MC(50mL)进行萃取,合并有机相,使用无水硫酸镁进行干燥,过滤,减压除去溶剂;所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯,得到白色固体中间体I-H-1(12.84g,63.94%)。
将中间体I-H-1(10.0g,32.76mmol),4-氨基对三联苯(8.28g,33.74mmol),三(二亚苄基丙酮)二钯(0.30g,0.33mmol),2-二环己基磷-2’,4’,6’-三异丙基联苯(0.31g,0.66mmol)以及叔丁醇钠(4.72g,49.14mmol)加入甲苯(100mL)中,氮气保护下加热至108℃,搅拌5h;而后冷却至室温,反应液使用去离子水洗后加入无水硫酸镁干燥,过滤后将滤液通过短硅胶柱,减压除去溶剂;所得粗品使用二氯甲烷/正庚烷(1:5)为流动相进行硅胶柱色谱提纯,之后用二氯甲烷/正庚烷体系对粗品进行重结晶提纯,得到灰白色固体中间体I-H(10.96g,71.22%)。
将2-溴-7-碘-9,9-二甲基芴(10.0g,25.06mmol),N-(4-(-1-萘基)苯基)-4-联苯胺(6.39g,17.21mmol),三(二亚苄基丙酮)二钯(0.15g,0.16mmol),三叔丁基膦(0.07g,0.33mmol)以及叔丁醇钠(2.41g,23.5mmol)加入甲苯(100mL)中,氮气保护下加热至18℃,搅拌16h;而后冷却至室温,反应液过滤后将滤液减压除去溶剂;所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯,之后用正庚烷对粗品进行重结晶提纯,得到淡黄色固体中间体II-H(3.07g,28.58%)。
将中间体I-H(2.20g,4.68mmol),中间体II-H(3.00g,4.68mmol),三(二亚苄基丙酮)二钯(0.09g,0.09mmol),2-二环己基磷-2’,6’-二甲氧基联苯(0.08g,0.19mmol)以及叔丁醇钠(0.68g,7.03mmol)加入甲苯(30mL)中,氮气保护下加热至108℃,搅拌4h;而后冷却至室温,反应液过滤后将滤液减压除去溶剂;使用二氯甲烷/乙酸乙酯体系对粗品进行重结晶提纯,得到白色固体化合物8(2.18g,45.13%)。质谱:m/z=1031.5(M+H)+
合成例9
化合物9的合成
将3-氨基-4’-甲基联苯(5.00g,27.29mmol),3-溴-5'-苯基-1,1':3',1”-三联苯(10.21g,26.49mmol),三(二亚苄基丙酮)二钯(0.49g,0.53mmol),2-二环己基磷-2’,4’,6’-三异丙基联苯(0.50g,1.06mmol)以及叔丁醇钠(3.82g,39.74mmol)加入甲苯(100mL)中,氮气保护下加热至108℃,搅拌6h;而后冷却至室温,反应液过滤后将滤液减压除去溶剂;所得粗品使用二氯甲烷/正庚烷对粗品进行重结晶提纯,得到白色固体中间体II-I-1(8.69g,69.41%)。
将中间体II-I-1(5.00g,10.25mmol),1-溴-4-碘萘(5.12g,15.38mmol),三(二亚苄基丙酮)二钯(0.19g,0.21mmol),三叔丁基膦(0.08g,0.41mmol)以及叔丁醇钠(1.48g,15.38mmol)加入甲苯(50mL)中,氮气保护下加热至108℃,搅拌7h;而后冷却至室温,反应液过滤后将滤液减压除去溶剂;所得粗品使用二氯甲烷/正庚烷(1:8)为流动相进行硅胶柱色谱提纯,之后用二氯甲烷/正庚烷对粗品进行重结晶提纯,得到灰白色固体中间体II-I(3.61g,54.86%)
将上述合成例1中的中间体I-A(1.70g,5.60mmol),中间体II-I(3.60g,5.60mmol),三(二亚苄基丙酮)二钯(0.10g,0.11mmol),2-二环己基磷-2’,6’-二甲氧基联苯(0.09g,0.22mmol)以及叔丁醇钠(0.81g,8.4mmol)加入甲苯(30mL)中,氮气保护下加热至108℃,搅拌4h;而后冷却至室温,反应液过滤后将滤液减压除去溶剂;使用二氯甲烷/乙酸乙酯体系对粗品进行重结晶提纯,得到白色固体化合物9(2.04g,39.84%)。质谱:m/z=915.5(M+H)+
合成例10
化合物10的合成
将上述合成例1中的中间体I-A-1(5.00g,17.17mmol),2-氨基-9,9二甲基芴(3.70g,17.68mmol),三(二亚苄基丙酮)二钯(0.31g,0.34mmol),2-二环己基磷-2’,4’,6’-三异丙基联苯(0.32g,0.69mmol)以及叔丁醇钠(2.47g,25.75mmol)加入甲苯(50mL)中,氮气保护下加热至108℃,搅拌3h;而后冷却至室温,反应液使用去离子水洗后加入无水硫酸镁干燥,过滤后将滤液通过短硅胶柱,减压除去溶剂;使用二氯甲烷/正庚烷体系对粗品进行重结晶提纯,得到白色固体中间体I-J(5.85g,81.25%)。
将N,9-二苯基-9H-咔唑-3-胺(5.00g,14.95mmol),4-溴-4’-碘联苯(8.05g,22.43mmol),三(二亚苄基丙酮)二钯(0.27g,0.30mmol),三叔丁基膦(0.12g,0.60mmol)以及叔丁醇钠(2.16g,22.43mmol)加入甲苯(80mL)中,氮气保护下加热至108℃,搅拌6h;而后冷却至室温,反应液过滤后将滤液减压除去溶剂;所得粗品使用正庚烷为流动相进行硅胶柱色谱提纯,之后二氯甲烷/正庚烷对粗品进行重结晶提纯,得到黄色固体中间体II-J(3.10g,36.64%)
将中间体I-J(2.30g,5.48mmol),中间体II-J(3.10g,5.48mmol),三(二亚苄基丙酮)二钯(0.10g,0.11mmol),2-二环己基磷-2’,6’-二甲氧基联苯(0.09g,0.22mmol)以及叔丁醇钠(0.79g,8.22mmol)加入甲苯(30mL)中,氮气保护下加热至108℃,搅拌2h;而后冷却至室温,反应液过滤后将滤液减压除去溶剂;使用二氯甲烷/正庚烷体系对粗品进行重结晶提纯,得到白色固体化合物10(2.36g,47.58%)。质谱:m/z=904.5(M+H)+
合成例11:化合物11的合成
除了使用5.64g(15mmol)4-氨基-4’-甲基联苯和5.23g(16.5mmol)中间体II-E-1之后,与合成例1相同的方法合成了化合物11。质谱:m/z=942.3(M+H)+
合成例12:化合物12的合成
除了使用5.42g(15mmol)2-萘胺和5.33g(16.5mmol)中间体II-E-1之后,与合成例1相同的方法合成了化合物12。质谱:m/z=902.2(M+H)+
合成例13:化合物13的合成
除了使用3.11g(15mmol)对甲苯胺和5.06g(16.5mmol)4-溴-4'-氯-2,3-二甲基-1,1'-联苯之后,与合成例6相同的方法合成了化合物13。质谱:m/z=770.1(M+H)+
合成例14:化合物14的合成
除了使用4.96g(15mmol)2-溴联苯之后,与合成例3相同的方法合成了化合物14。质谱:m/z=790.0(M+H)+
合成例15:化合物15的合成
除了使用5.73g(15mmol)3-氨基联苯之后,与合成例6相同的方法合成了化合物15。质谱m/z=699.9(M+H)+
合成例16:化合物16的合成
除了使用5.64g(15mmol)3-溴-4’-碘联苯,与合成例1相同的方法合成了化合物16。质谱:m/z=623.9(M+H)质谱:m/z=623.9(M+H)+
合成例17:化合物17的合成
除了使用4.45g(15mmol)1-(3-溴苯基)金刚烷之后,与合成例1相同的方法合成了化合物17。质谱m/z=623.9M+H)+
合成例18:化合物18的合成
除了使用5.91g(15mmol)II-E-1之后,与合成例5相同的方法合成了化合物18。质谱m/z=1016.5(M+H)+
合成例19:化合物19的合成
除了使用5.28g(15mmol)4-氨基联苯、5.35g(16.5mmol)4溴-4’甲基联苯和4.29g(13.5mmol)对氯苯硼酸之后,与合成例6相同的方法合成了化合物19。质谱m/z=1017.5(M+H)+
合成例20:化合物20的合成
除了使用6.06g(15mmol)9-(4-溴苯基)咔唑、3.17g(16.5mmol)苯胺和4.29g(13.5mmol)对氯苯硼酸之后,与合成例6相同的方法合成了化合物20。质谱m/z=1045.5(M+H)+
合成例21:化合物21的合成
除了使用5.19g(15mmol)2-溴-5-碘代苯和6.24g(16.5mmol)4-氯-3-甲基联苯-4’-基硼酸之后,与合成例6相同的方法合成了化合物21。质谱:m/z=850.4(M+H)+
合成例22:化合物22的合成
除了使用5.17g(15mmol)二苯胺5.81g(16.5mmol)4-溴-4'-碘-联苯和4.29g(13.5mmol)间氯苯硼酸之后,与合成例5相同的方法合成了化合物22。质谱:m/z=983.5(M+H)+
合成例23:化合物23的合成
除了使用3.11g(15mmol)对甲苯胺和5.47g(16.5mmol)3-溴二苯并呋喃之后,与合成例6相同的方法合成了化合物23。质谱:m/z=851.4(M+H)+
合成例24:化合物24的合成
除了使用5.42g(15mmol)4氯联苯-4’硼酸和5.56g(16.5mmol)4-氨基联苯之后,与合成例1相同的方法合成了化合物24。质谱:m/z=891.5(M+H)+
合成例25:化合物25的合成
除了使用5.42g(15mmol)4氯联苯-3’硼酸和6.09g(16.5mmol)2-氨基-9,9-二甲基芴之后,与合成例1相同的方法合成了化合物25。质谱:m/z=895.4(M+H)+
合成例26:化合物26的合成
除了使用5.93g(15mmol)3-二苯并噻吩胺和5.84g(16.5mmol)3-溴二苯并呋喃之后,与合成例1相同的方法合成了化合物26。质谱:m/z=981.5(M+H)+
合成例27:化合物27的合成
除了使用3.11g(15mmol)对甲苯胺和5.98g(16.5mmol))2-氨基-9,9-二甲基芴之后,与合成例1相同的方法合成了化合物27。质谱:m/z=713.3(M+H)+
制作有机电致发光器件
实施例1:使用本发明化合物作为空穴传输层的有机电致发光器件
通过以下过程制备阳极:将厚度为的ITO基板(康宁制造)切割成40mm×40mm×0.7mm的尺寸,采用光刻工序,将其制备成具有阴极、阳极以及绝缘层图案的实验基板,利用紫外臭氧以及O2:N2等离子进行表面处理,以增加阳极(实验基板)的功函数的和清除浮渣。
将DBimiBphen和LiQ以1:1的重量比进行混合并蒸镀形成了厚的电子传输层(ETL),将LiQ蒸镀在电子传输层上以形成厚度为的电子注入层(EIL),然后将镁(Mg)和银(Ag)以1:9的蒸镀速率混合,真空蒸镀在电子注入层上,形成厚度为的阴极。
此外,在上述阴极上蒸镀了厚度为65nm的N-(4-(9H-咔唑-9-基)苯基)-4'-(9H-咔唑-9-基)-N-苯基-[1,1'-联苯]-4-胺,形成覆盖层(CPL),从而完成有机发光器件的制造。
实施例2-7
除了在形成空穴传输层(HTL)使用表1中所示的化合物以外,利用与实施例1相同的方法制作有机电致发光器件。
器件性能见表1。
比较例1~比较例3
在所述比较例1~比较例3中,除了使用了NPB、化合物A和化合物B作为空穴传输层替代化合物1之外,用与实施例1相同的方法制造有机电致发光器件。
即比较例1采用NPB制造有机电致发光器件,比较例2采用化合物A制造有机电致发光器件,比较例3采用化合物B制造有机电致发光器件,器件性能见表1。
对上述制得的有机电致发光器件,在20mA/cm2的条件下分析了器件的性能,其结果示于下表1。
表1
实施例 | 化合物 | Volt(V) | Cd/A | EQE(%) | T95(hrs) | CIEx | CIEy |
实施例1 | 化合物1 | 4.0 | 6.7 | 14.3 | 200 | 0.140 | 0.045 |
实施例2 | 化合物2 | 4.1 | 6.8 | 14.6 | 210 | 0.141 | 0.044 |
实施例3 | 化合物3 | 3.9 | 6.9 | 14.9 | 198 | 0.141 | 0.045 |
实施例4 | 化合物4 | 4.2 | 7.2 | 15.1 | 209 | 0.141 | 0.042 |
实施例5 | 化合物5 | 3.8 | 6.4 | 14.7 | 180 | 0.142 | 0.044 |
实施例6 | 化合物6 | 3.9 | 6.6 | 14.3 | 176 | 0.143 | 0.043 |
实施例7 | 化合物7 | 4.4 | 6.4 | 14.4 | 169 | 0.142 | 0.042 |
比较例1 | NPB | 5.0 | 4.0 | 6.4 | 80 | 0.142 | 0.043 |
比较例2 | 化合物A | 4.6 | 5.4 | 9.8 | 120 | 0.141 | 0.044 |
比较例3 | 化合物B | 4.4 | 5.9 | 10 | 160 | 0.141 | 0.043 |
参见上述表1器件评价结果可知,实施例1-7将本发明的化合物用作空穴传输层(HTL)的情况下,与比较例1-3中的化合物相比,在色坐标CIEy相差不大的情况下,在相同电流密度下进行测试,用本发明的化合物制作的有机电致发光器件,驱动电压(V)明显降低,电流效率(Cd/A)和外量子效率(EQE)提升明显优于比较例,呈现出提升的趋势,而使用寿命(T95)也显著增加。比较例2中的化合物A虽然也是金刚烷基连接双胺化合物的结构,但是与本发明的不同之处在于本发明中与金刚烷基与双胺化合物相连的基团为苯基、联苯基或三联苯基,而化合物A是以二甲基芴基相连。二甲基芴基在高温条件下容易发生断裂,发生断裂的位置,首先是两个甲基先发生断裂,其次芴基中的五元环。将其制成有机电致发光器件,容易在高温下发生结晶,导致器件性能降低,特别是发光效率和寿命会严重降低,驱动电压也会升高。
而本发明中的苯、联苯、三联苯都为相对稳定的结构,在高温环境下不易发生断裂,不会使器件在高温环境下发生结晶。因此,将本发明化合物用作有机电致发光器件的空穴传输层,具有降低驱动电压、提高发光效率以及延长使用寿命的特性。
实施例8:使用本发明化合物作为电子阻挡层的有机电致发光器件
通过以下过程制备阳极:将厚度为的ITO基板(康宁制造)切割成40mm×40mm×0.7mm的尺寸,采用光刻工序,将其制备成具有阴极、阳极以及绝缘层图案的实验基板,利用紫外臭氧以及O2:N2等离子进行表面处理,以增加阳极(实验基板)的功函数的和清除浮渣。
将DBimiBphen和LiQ以1:1的重量比进行混合并蒸镀形成了厚的电子传输层(ETL),将LiQ蒸镀在电子传输层上以形成厚度为的电子注入层(EIL),然后将镁(Mg)和银(Ag)以1:9的比例混合,真空蒸镀在电子注入层上,形成厚度为的阴极。
实施例9-10
除了在形成电子阻挡层(EBL)时各自使用表2中所示的化合物以外,利用与实施例8相同的方法制作有机电致发光器件。
即实施例9采用本发明化合物9制作有机电致发光器件,实施例10采用本发明化合物10制作有机电致发光器件。
器件性能见表2
比较例4~比较例6
在所述比较例4~比较例6中,除了使用了TCTA、NPD、TPD作为电子阻挡层替代化合物6之外,用与实施例6相同的方法制造有机电致发光器件。
即比较例4采用TCTA制造有机电致发光器件,比较例5采用NPD制造有机电致发光器件,比较例6采用TPD制造有机电致发光器件,器件性能见表2。
对上述制得的有机电致发光器件,在20mA/cm2的条件下分析了器件的性能,其结果示于下表2。
表2
实施例 | 化合物 | Volt(V) | Cd/A | EQE(%) | T95(hrs) | CIEx | CIEy |
实施例8 | 化合物8 | 4.1 | 6.5 | 12.1 | 152 | 0.141 | 0.043 |
实施例9 | 化合物9 | 3.7 | 6.1 | 14.4 | 178 | 0.143 | 0.043 |
实施例10 | 化合物10 | 4.5 | 6.1 | 13.2 | 186 | 0.142 | 0.042 |
比较例4 | TCTA | 5.0 | 5.1 | 8.3 | 75 | 0.141 | 0.044 |
比较例5 | NPD | 6.5 | 4.2 | 8.7 | 68 | 0.140 | 0.043 |
比较例6 | TPD | 5.7 | 4.9 | 9.5 | 59 | 0.144 | 0.045 |
参见上述表2器件评价结果可知,实施例8-10将本发明的化合物用作电子阻挡层(EBL)的情况下,与比较例4-6中的化合物相比,在色坐标CIEy相差不大的情况下,在相同电流密度下进行测试,用本发明的化合物制作的有机电致发光器件,驱动电压(V)明显降低,电流效率(Cd/A)和外量子效率(EQE)提升明显优于比较例,呈现出提升的趋势,而使用寿命(T95)也显著增加。
从表2可知,本发明化合物用于蓝光器件的电子阻挡层时,与比较例相比,外量子效率提高了27%~75%,这对蓝光器件而言,是非常显著的提升。对于OLED器件(即有机电致发光器件)来说,对其效果(例如EQE方面)的改善即使在数据上看来只有百分之几,但是,这种改善也是非常显著的。
具体地说,外量子效率(EQE)可以按照如下公式计算,例如EQE=射出组件的光子数目/注入电子数目;又例如EQE=出光率*内部量子效率(出光率小于1)。
对于蓝光器件而言,发光层用的是荧光材料,而荧光材料是单线态激子发光,其内部量子效率最高为25%。而对外发光时,由于耦合等器件结构所导致的光的损失等其他原因,因为只能利用25%的激子,导致外量子效率一定低于25%,使得其效率通常较低。
因此,使用本发明化合物制作的器件,具有降低驱动电压、提高发光效率以及延长使用寿命的特性。
综上所述,将本发明化合物用作有机电致发光器件的空穴传输层或电子阻挡层,使得包含该化合物的有机电致发光器件具有更低的驱动电压、更高的发光效率和更好的寿命。
以上实施例只是对本发明的化合物的进一步说明,本发明的发明要求保护范围并不限定于此。对本发明所属领域的普通技术人员而言,在不脱离发明要求保护范围中所记载的本发明的技术思想的范围下,对本发明进行的各种补充及变形也属于本发明的保护范围。
Claims (7)
4.一种有机电致发光器件,其特征在于,包括阴极、阳极以及设置在所述阴极和阳极之间的一层以上的有机层,所述有机层至少有一层包含权利要求1或权利要求3所述的电致发光材料。
5.根据权利要求4所述的有机电致发光器件,其特征在于,所述有机层包括空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层以及电子注入层。
6.根据权利要求5所述的有机电致发光器件,其特征在于,所述空穴传输层包含权利要求1所述的电致发光材料。
7.根据权利要求5所述的有机电致发光器件,其特征在于,所述电子阻挡层包含权利要求1所述的电致发光材料。
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