CN112940013A - 一种咪唑并吡啶的芳胺类化合物及其应用 - Google Patents
一种咪唑并吡啶的芳胺类化合物及其应用 Download PDFInfo
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- CN112940013A CN112940013A CN201911268938.0A CN201911268938A CN112940013A CN 112940013 A CN112940013 A CN 112940013A CN 201911268938 A CN201911268938 A CN 201911268938A CN 112940013 A CN112940013 A CN 112940013A
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- unsubstituted
- substituted
- alkyl
- heteroaryl
- compound
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- -1 Arylamine compound Chemical class 0.000 title claims abstract description 15
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 67
- 239000000463 material Substances 0.000 claims abstract description 40
- 238000000605 extraction Methods 0.000 claims abstract description 17
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 52
- 125000001072 heteroaryl group Chemical group 0.000 claims description 29
- 125000003118 aryl group Chemical group 0.000 claims description 26
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 24
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 22
- 229910052805 deuterium Inorganic materials 0.000 claims description 22
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
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- 125000001624 naphthyl group Chemical group 0.000 claims description 12
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
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Classifications
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- 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
- 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
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- 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
-
- 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
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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
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- 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
- H10K50/858—Arrangements for extracting light from the devices comprising refractive means, e.g. lenses
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- H—ELECTRICITY
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- 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
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- H—ELECTRICITY
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- 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
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- 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
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- 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
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- 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
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- 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
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Abstract
本发明涉及一种咪唑并吡啶的芳胺类化合物及其应用。所述化合物具有式(I)结构。本发明化合物具有升华温度低,热稳定性好,折射率高、可见光区折射率差异小等优点,可做为光提取层材料,应用于有机发光器件中。
Description
技术领域
本发明涉及有机电致发光材料领域,特别涉及咪唑并吡啶的芳胺类化合物及其在有机电致发光器件上的应用。
背景技术
目前,作为新一代显示技术的有机电致发光器件(OLED)在显示和照明技术方面都获得了越来越多的关注,应用前景十分广泛。但是,和市场应用要求相比,OLED器件的发光效率、驱动电压、使用寿命等性能还需要继续加强和改进。
一般来说,OLED器件基本结构为在金属电极中间夹杂各种不同功能的有机功能材料薄膜,犹如一个三明治的结构,在电流的驱动下,从阴阳两极分别注入空穴和电子,空穴和电子在移动一段距离后,在发光层得到复合,并以光或热的形式进行释放,从而产生了OLED的发光。然而,有机功能材料是有机电致发光器件的核心组成部分,材料的热稳定性、光化学稳定性、电化学稳定性、量子产率、成膜稳定性、结晶性、色饱和度等都是影响器件性能表现的主要因素。
一方面,如何缩小OLED器件内外量子效率之间的巨大差距,如何减少器件中的全发射效应、提高光耦合提取比例引起人们的广泛关注。现行的光提取层的材料的折射率都比较低,尤其是在红光波段,通常折射率小于1.85,极少数大于1.90,更少数大于2.0。另外,现有的光提取材料在红绿蓝光波段区域的折射率差别较大,造成三种颜色光的最佳厚度差别大,未能充分体现光提取材料的性能。对于顶发射器件来说,光提取层材料的折射率越大,相应的外量子效率就越高,器件的发光效率就越高。所以,开发高折射率的光提取层材料尤为重要。CN103828485和TW201506128公开了以多联苯二胺为核心的光提取层材料,但是折射率还是稍微偏低,尤其是在红光方面更需要进一步提升。
发明内容
针对上述领域中的缺陷,本发明提供一种咪唑并吡啶的芳胺类化合物,该类化合物具有升华温度低,热稳定性好,折射率高、可见光区折射率差异小等优点,可用于有机发光器件中。
一种咪唑并吡啶的芳胺类化合物,其结构式为式I所示:
其中n为1或2;
X1、X2、X3、X4独立的表示为CR0或者N,R0独立的选自氢、氘、卤素、C1-C8烷基、C1-C8杂烷基、芳烷基、氨基、硅烷基、取代或未取代的C6-C60的芳基、取代或未取代的C1-C60的杂芳基、腈、异腈,且相邻的R0能键接成并环;
其中R1为单键、C1-C30亚烷基、C1-C30亚杂烷基、C3-C30亚环烷基、取代或未取代的C6-C30的亚芳基、取代或未取代的C2-C28的亚杂芳基;
其中R2独立的选自氢、氘、卤素、C1-C30烷基、C1-C30杂烷基、C3-C30环烷基、C1-C30烷氧基、C6-C60芳氧基、氨基、硅烷基、腈基、异腈基、膦基、取代或未取代的C6-C60的芳基、取代或未取代的C1-C60的杂芳基;
其中Ar1为取代或未取代的C6-C60的芳基、取代或未取代的C6-C60的杂芳基、经取代或未经取代C3-C60环烷基、取代或未取代的C6-C60的芳胺基;
其中B为取代或未取代的C6-C60的芳基或亚芳基、取代或未取代的C6-C60的杂芳基或亚杂芳基、经取代或未经取代的C3-C60环烷基或亚环烷基、取代或未取代的C6-C60的芳胺基或亚芳胺基;
其中杂烷基或杂芳基中的一个或多个碳原子由选自O、S、N、Se、Si、Ge中的至少一个杂原子替换;所述取代为被氘、卤素、C1-C30烷基、苯基、萘基或联苯基取代。
优选:其结构式如式II所示
其中R1为单键、C1-C10亚烷基、C1-C10亚杂烷基、C3-C10亚环烷基、取代或未取代的C6-C30的亚芳基、取代或未取代的C2-C28的亚杂芳基;
其中R2独立的选自氢、氘、卤素、C1-C10烷基、C1-C10杂烷基、C1-C10烷氧基、C3-C30环烷基、C6-C30芳氧基、氨基、硅烷基、腈、异腈、膦基、取代或未取代的C6-C30的芳基、取代或未取代的C1-C30的杂芳基;
其中Ar1、Ar2为取代或未取代的C6-C30的芳基、取代或未取代的C6-C30的杂芳基、经取代或未经取代的单环或多环C3-C30脂肪族环或芳香族环、取代或未取代的C6-C30的芳胺基;
其中杂烷基或杂芳基中的一个或多个碳原子由选自O、S、N、Si中的至少一个杂原子替换;所述取代为被氘、卤素、C1-C8烷基、苯基、萘基或联苯基取代。
优选:其中R1为C1-C8烷基取代或未取代的C6-C20的亚芳基、C1-C8烷基取代或未取代的C2-C18的亚杂芳基;其中R2为C1-C8烷基、C1-C8烷基取代或未取代的C6-C20的芳基、C1-C8烷基取代或未取代的C1-C20的杂芳基;其中Ar1、Ar2为取代或未取代的C6-C20的芳基、取代或未取代的C6-C20的杂芳基、经取代或未经取代的单环或多环C3-C20脂肪族环或芳香族环、取代或未取代的C6-C20的芳胺基;其中杂烷基或杂芳基中的一个或多个碳原子由选自O、S、N中的至少一个杂原子替换;所述取代为被氘、C1-C8烷基、苯基、萘基或联苯基取代。
更优选:其中R1为C1-C4烷基取代或未取代的C6-C10的亚芳基、C1-C4烷基取代或未取代的C2-C8的亚杂芳基;其中Ar1、R2为C1-C4烷基取代或未取代的C6-C10的芳基、C1-C4烷基取代或未取代的C1-C8的杂芳基;其中Ar2为取代或未取代的C6-C20的芳基、取代或未取代的C6-C20的杂芳基、经取代或未经取代的单环或多环C3-C20脂肪族环或芳香族环、取代或未取代的C6-C20的芳胺基;其中杂烷基或杂芳基中的一个或多个碳原子由选自O、S、N中的至少一个杂原子替换;所述取代为被氘、C1-C4烷基、苯基、萘基或联苯基取代。
作为优选的化合物,Ar1或Ar2至少之一含有以下结构式(III),其中R1为单键、C1-C8亚烷基、C1-C8亚杂烷基、C3-C8亚环烷基、C1-C8烷基取代或未取代的C6-C30的亚芳基、C1-C8烷基取代或未取代的C2-C28的亚杂芳基;其中R2为氢、氘、卤素、C1-C8烷基、C1-C8杂烷基、C3-C8环烷基、C1-C8烷基取代或未取代的C6-C30的芳基、C1-C8烷基取代或未取代的C1-C30的杂芳基。
作为优选的化合物,可为以下式(IV)结构,其中R1为单键、C1-C8亚烷基、C1-C8亚杂烷基、C3-C8亚环烷基、C1-C8烷基取代或未取代的C6-C30的亚芳基、C1-C8烷基取代或未取代的C2-C28的亚杂芳基;其中R2为氢、氘、卤素、C1-C8烷基、C1-C8杂烷基、C3-C8环烷基、C1-C8烷基取代或未取代的C6-C30的芳基、C1-C8烷基取代或未取代的C1-C30的杂芳基;其中Ar1为取代或未取代的C6-C30的芳基、取代或未取代的C6-C30的杂芳基、经取代或未经取代的单环或多环C3-C30脂肪族环或芳香族环,A为取代或未取代的C6-C30的亚芳基、取代或未取代的C6-C30的亚杂芳基;其中杂烷基或杂芳基中的一个或多个碳原子由选自O、S、N、Si中的至少一个杂原子替换;所述取代为被氘、卤素、C1-C8烷基、苯基、萘基或联苯基取代。
优选:其中R1为C1-C8烷基取代或未取代的C6-C20的亚芳基、C1-C8烷基取代或未取代的C2-C18的亚杂芳基;其中R2为C1-C8烷基、C1-C8烷基取代或未取代的C6-C20的芳基、C1-C8烷基取代或未取代的C1-C20的杂芳基;其中Ar1为取代或未取代的C6-C20的芳基、取代或未取代的C6-C20的杂芳基、经取代或未经取代的单环或多环C3-C20脂肪族环或芳香族环,A为取代或未取代的C6-C20的亚芳基、取代或未取代的C6-C20的亚杂芳基;其中杂烷基或杂芳基中的一个或多个碳原子由选自O、S、N中的至少一个杂原子替换;所述取代为被氘、C1-C8烷基、苯基、萘基或联苯基取代。
优选:X1、X2、X3、X4独立的表示为CR0,R0独立的选自氢、C1-C8烷基。
作为优选的化合物为以下化合物:
作为优选的化合物为以下化合物:
所述应用为化合物作为OLED器件的光提取层材料。
本发明的咪唑并吡啶的芳胺类化合物材料具有升华温度低,热稳定性好,发光效率高,折射率高、可见光区折射率差异小等优点,可用于有机发光器件中。作为光提取层材料,该器件具有发光效率高、长时间热稳定性好的优点,具有应用于AMOLED产业的可能。
具体实施方式(合成和器件实施)
下述实施例仅为了便于理解技术发明,不应视为本发明的具体限制。
本发明中的化合物合成中涉及的原物料和溶剂等均购自于Alfa、Acros等本领域技术人员熟知的供应商。
实施例1:
(1)化合物A1的合成:
化合物03的合成:向一个2L三口瓶,依次将化合物01(80g,256.4mmol,1.0eq)、化合物02(71.64g,769.2mmol,3.0eq),t-BuONa(49.2g,512.8mmol,2.0eq)、Pd2(dba)3(2.35g,2.56mmol,0.01eq),X-phos(2.44g,5.13mmol,0.02eq),分子筛干燥的甲苯(800ml)投入到烧瓶中,真空、氮气置换3次,油浴加热到108度左右,保温搅拌回流2h,取样点板01原料反应完。反应液降温至80℃,滴加甲醇(800ml)搅拌1h,降至室温后抽滤,得到固体加入THF(900ml)和正己烷(600ml)热打浆2h,抽滤,烘干得到71.5g类白色固体,收率82.8%。质谱:337.4(M+H)
化合物06的合成:向一个2L单口瓶,依次将化合物04(76g,214.6mmol,1.0eq)、化合物05(50.5g,536.6mmol,2.5q),NaHCO3(27.05g,322mmol,1.5eq)、异丙醇(700ml)投入到烧瓶中,油浴加热到80度左右,保温搅拌回流7h,取样点板原料反应完。降温,滴加去离子水,搅拌2h左右,抽滤。固体用乙酸乙酯打浆,抽滤烘干。得到54.5g白色固体化合物06,收率72.7%。质谱:349.2(M+H)
化合物A1的合成:向一个2L三口瓶,依次将化合物06(45.7,130.8mmol,2.2eq)、化合物03(20g,59.4mmol,1eq),t-BuONa(17.1g,178.3mmol,3.0eq)、Pd2(dba)3(1.09g,1.19mmol,0.02eq),X-phos(1.13g,2.38mmol,0.04eq),分子筛干燥的甲苯(600ml)投入到烧瓶中,真空、氮气置换3次,油浴加热到108度左右,保温搅拌回流16h,取样点板06原料反应完。反应液降温至80℃,滴加正己烷(800ml)搅拌1h,降至室温后抽滤,得到固体加入二氯甲烷(1.6L)溶解完全,去离子水洗四次(500ml*4),分液后有机相用硅胶过滤,少量二氯甲烷冲洗硅胶,浓缩有机相得到固体,采用四氢呋喃/甲醇(250ml/300ml)进行重结晶2次,烘干得到32g淡黄色固体,收率61.6%。得到的合成品经过升华纯化得到21.2克淡黄色固体化合物A1,收率66.2%。质谱:874.1(M+H)。
1HNMR(400MHz,CDCl3)δ8.01(d,J=6.8Hz,2H),7.72(d,J=8.0Hz,3H),7.64(d,J=9.0Hz,2H),7.51(d,J=8.3Hz,4H),7.40–7.13(m,23H),7.10(d,J=7.2Hz,2H),6.74(d,J=6.8Hz,2H)。
(2)化合物A16的合成:
化合物08的合成:选取对应的材料,参照化合物03的合成方式和处理方法,只需要将对应的原物料变更即可。质谱:412.5(M+H)
化合物A16的合成:选取对应的材料,参照化合物A1的合成、升华得到黄色固体化合物A16。质谱:949.1(M+H)。1H NMR(400MHz,CDCl3)δ8.48(d,2H),7.73(dd,4H),7.58–7.44(m,12H),7.37(m,8H),7.33–7.17(m,14H),7.08(d,4H),7.00(d,2H),6.86(d,2H)。
(3)化合物A17的合成:
化合物10的合成:选取对应的材料,参照化合物03的合成方式和处理方法,只需要将对应的原物料变更即可。质谱:377.5(M+H)
化合物A17的合成:选取对应的材料,参照化合物A1的合成、升华得到黄色固体化合物A17。质谱:913.1(M+H)。1HNMR(400MHz,CDCl3)δ8.48(d,2H),7.86(d,2H),7.73(dd,4H),7.49(dd,J=14.4,9.4Hz,10H),7.37(m,4H),7.25(dd,J=28.1,8.1Hz,12H),7.08(m,4H),7.00(d,2H),6.86(d,2H),1.69(s,6H)。
(4)化合物A22的合成:
化合物12的合成:选取对应的材料,参照化合物06的合成方式和处理方法,只需要将对应的原物料变更即可。质谱:349.03(M+H)
化合物A22的合成:选取对应的材料,参照化合物A1的合成、升华得到黄色固体化合物A22。质谱:873.1(M+H)。1HNMR(400MHz,CDCl3)δ8.48(d,2H),7.73(dd,4H),7.60–7.42(m,12H),7.37(m,8H),7.33–7.16(m,10H),7.04(d,J=40.0Hz,6H),6.86(d,2H).
(5)化合物B86的合成:
化合物14的合成:选取对应的材料,参照化合物06的合成方式和处理方法,只需要将对应的原物料变更即可。质谱:397.30(M+H);
化合物15的合成:选取对应的材料,参照化合物03的合成方式和处理方法,只需要将对应的原物料变更即可。质谱:361.4(M+H);
化合物17的合成:向一个2L三口瓶,依次将化合物15(45g,124.5mmol,1.0eq)、化合物16(36.98g,130.7mmol,1.05eq),CuI(2.37g,12.45mmol,2eq)、1,10-菲罗啉(4.49g,24.9mmol,0.2eq),K2CO3(34.41g,2.49mmol,0.04eq),DMF(450ml)投入到烧瓶中,真空、氮气置换3次,油浴加热到120度左右,保温搅拌8h,取样点板15原料反应完。反应液降温至40℃,滴加去离子水(800ml)搅拌1h,降至室温后过滤,得到固体加入甲苯(400ml)溶解完全,去离子水洗(100ml*3),分液后有机相用硅胶过滤,少量甲苯冲洗硅胶,浓缩有机相至剩余250ml,再滴加甲醇(300ml)进行析晶,过滤烘干得到50.34g米白色固体化合物17,收率78.3%。质谱:516.4(M+H)
化合物18的合成:向一个1L单口瓶,依次将化合物17(32.5g,62.9mmol,1.0eq)、联硼酸频那醇酯(19.18g,75.52mmol,1.2eq),Pd(dppf)Cl2(0.92g,1.26mmol,0.02eq)、醋酸钾(12.35g,125.8mmol,2eq),二氧六环(350ml)投入到烧瓶中,油浴加热到100度左右,保温搅拌6h,取样点板17原料反应完。反应液降温至40℃,反应液减压浓缩至200ml,加入甲醇(400ml)室温下搅拌2h,过滤,得到固体加入正己烷(400ml)在50℃时打浆2h,过滤烘干得到30.35g米白色固体化合物18,收率86.1%。质谱:563.5(M+H)
化合物B86的合成:向一个1L三口瓶,依次将化合物18(28.0g,49.69mmol,1.0eq)、化合物19(23.67g,49.69mmol,1.0eq),K2CO3(13.73g,99.38mmol,2.0eq)、Pd132(0.35g,0.49mmol,0.01eq),甲苯(280ml),乙醇(56ml)去离子水(56ml)投入到烧瓶中,真空、氮气置换3次,油浴加热到75度左右,保温搅拌回流16h,取样点板18原料反应完。反应液降温至60度,加入甲苯(200ml),去离子水(100ml),搅拌1h,分液,分液后有机相用硅胶过滤,少量甲苯冲洗硅胶,浓缩有机相得到固体,采用甲苯/甲醇(220ml/250ml)进行重结晶3次,烘干得到29.47g淡黄色固体,收率71.2%。得到的合成品经过升华纯化得到22.3克淡黄色固体化合物B86,收率75.6%。质谱:833.1(M+H)。1H NMR(400MHz,CDCl3)δ8.48(d,1H),7.75(dd,4H),7.62–7.42(m,19H),7.39(m,J=20.0Hz,9H),7.33–7.14(m,7H),7.08(d,2H),7.00(d,1H),6.86(d,1H)。
(6)化合物B111的合成:
化合物B111的合成:选取对应的材料,参照化合物B86的合成方式和处理方法,只需要将对应的原物料变更即可。质谱:897.1(M+H)。1H NMR(400MHz,CDCl3)δ8.48(d,1H),7.96(m,6H),7.75(m,4H),7.60–7.34(m,16H),7.33-7.15(m,13H),7.08(d,2H),7.00(d,1H),6.86(d,1H)。
(7)化合物B130的合成:
化合物B130的合成:选取对应的材料,参照化合物B86的合成方式和处理方法,只需要将对应的原物料变更即可。质谱:913.2(M+H)。1H NMR(400MHz,CDCl3)δ8.48(d,1H),7.95–7.79(m,6H),7.60–7.44(m,14H),7.36(m,J=13.6Hz,7H),7.30–7.15(m,8H),7.08(d,2H),7.00(d,1H),6.86(d,1H),1.69(s,12H)。
(8)化合物B137的合成:
化合物B137的合成:选取对应的材料,参照化合物B86的合成方式和处理方法,只需要将对应的原物料变更即可。质谱:679.8(M+H)。1HNMR(400MHz,CDCl3)8.48(d,1H),8.13–7.94(m,3H),7.84(d,2H),7.63–7.46(m,9H),7.45–7.29(m,5H),7.29–7.13(m,9H),7.04(d,J=40.0Hz,3H),6.86(d,1H)。
应用例:
(1)化合物性能对比:本发明的化合物在OLED器件中可作为光提取层材料,具有较高的玻璃化转变温度、较高的折射率、可见光区较小的折射率差值。基本性能列于下表1
表1:折射率对比:
(2)有机电致发光器件的制作
将50mm*50mm*1.0mm的具有ITO(100nm)透明电极的玻璃基板在乙醇中超声清洗10分钟,再150度烘干后经过N2 Plasma处理30分钟。将洗涤后的玻璃基板安装在真空蒸镀装置的基板支架上,首先在有透明电极线一侧的面上按照覆盖透明电极的方式蒸镀化合物HATCN,形成膜厚为5nm的薄膜,紧接着蒸镀一层HTM1形成膜厚为60nm的薄膜,再在HTM1薄膜上蒸镀一层HTM2形成膜厚为10nm的薄膜,然后,在HTM2膜层上再采用共蒸镀的模式蒸镀主体材料CBP和掺杂材料,膜厚为30nm,主体材料和掺杂材料比例为90%:10%。在发光层上再依次按照下表的搭配蒸镀BCP(5nm)作为空穴阻隔层材料、Alq3(30nm)作为电子传输材料,接着在电子传输材料层之上蒸镀LiF(1nm)作为电子注入材料,接着再采用共蒸镀的模式蒸镀Mg/Ag(18nm,1:9)作为阴极材料,最后在阴极材料之上按照下表的搭配蒸镀CPL(50nm)作为光提取层材料。
器件性能评价
将上述器件进行器件性能测试,在各实施例和比较例中,使用恒定电流电源(Keithley2400),使用固定的电流密度流过发光元件,使用分光辐射俩都系(CS 2000)测试发光波谱,同时测定器件的发光效率。结果如下表2:
表2:
对比上述表2中的数据可知,使用本发明的化合物应用于有机电致发光器件的光提取层材料,相较于对比化合物发光效率表现出更加优越的性能。
如上所示,含有本发明结构的咪唑并吡啶的芳胺类化合物具有升华温度低,热稳定性好,折射率高、可见光区折射率差异小等优点,能够大幅改善光的取出效率、薄膜状态的稳定性。通过使用该系列化合物制备的OLED器件,能够得到较高的效率,并且改善其耐用性。综上所述,该类化合物作为光提取层材料,具有应用于AMOLED产业的可能。
Claims (10)
1.一种咪唑并吡啶的芳胺类化合物,其结构式如式(I)所示:
其中n为1或2;
其中X1、X2、X3、X4独立的表示为CR0或者N,R0独立的选自氢、氘、卤素、C1-C8烷基、C1-C8杂烷基、芳烷基、氨基、硅烷基、取代或未取代的C6-C60的芳基、取代或未取代的C1-C60的杂芳基、腈、异腈,且相邻的R0能键接成并环;
其中R1为单键、C1-C30亚烷基、C1-C30亚杂烷基、C3-C30亚环烷基、取代或未取代的C6-C30的亚芳基、取代或未取代的C2-C28的亚杂芳基;
其中R2独立的选自氢、氘、卤素、C1-C30烷基、C1-C30杂烷基、C3-C30环烷基、C1-C30烷氧基、C6-C60芳氧基、氨基、硅烷基、腈基、异腈基、膦基、取代或未取代的C6-C60的芳基、取代或未取代的C1-C60的杂芳基;
其中Ar1为取代或未取代的C6-C60的芳基、取代或未取代的C6-C60的杂芳基、C3-C60环烷基、取代或未取代的C6-C60的芳胺基;
其中B为取代或未取代的C6-C60的芳基或亚芳基、取代或未取代的C6-C60的杂芳基或亚杂芳基、C3-C60环烷基、取代或未取代的C6-C60的芳胺基或亚芳胺基;
其中杂烷基或杂芳基中的一个或多个碳原子由选自O、S、N、Se、Si、Ge中的至少一个杂原子替换;所述取代为被氘、卤素、C1-C30烷基、苯基、萘基或联苯基取代。
2.根据权利要求1所述的化合物,其结构式如式(II)所示:
其中R1为单键、C1-C10亚烷基、C1-C10亚杂烷基、C3-C10亚环烷基、取代或未取代的C6-C30的亚芳基、取代或未取代的C2-C28的亚杂芳基;
其中R2独立的选自氢、氘、卤素、C1-C10烷基、C1-C10杂烷基、C1-C10烷氧基、C3-C30环烷基、、C6-C30芳氧基、氨基、硅烷基、腈、异腈、膦基、取代或未取代的C6-C30的芳基、取代或未取代的C1-C30的杂芳基;
其中Ar1、Ar2为取代或未取代的C6-C30的芳基、取代或未取代的C6-C30的杂芳基、经取代或未经取代的单环或多环C3-C30脂肪族环或芳香族环、取代或未取代的C6-C30的芳胺基;
其中杂烷基或杂芳基中的一个或多个碳原子由选自O、S、N、Si中的至少一个杂原子替换;所述取代为被氘、卤素、C1-C8烷基、苯基、萘基或联苯基取代。
3.根据权利要求2所述的化合物,其中R1为C1-C8烷基取代或未取代的C6-C20的亚芳基、C1-C8烷基取代或未取代的C2-C18的亚杂芳基;其中R2为C1-C8烷基、C1-C8烷基取代或未取代的C6-C20的芳基、C1-C8烷基取代或未取代的C1-C20的杂芳基;其中Ar1、Ar2为取代或未取代的C6-C20的芳基、取代或未取代的C6-C20的杂芳基、经取代或未经取代的单环或多环C3-C20脂肪族环或芳香族环、取代或未取代的C6-C20的芳胺基;其中杂烷基或杂芳基中的一个或多个碳原子由选自O、S、N中的至少一个杂原子替换;所述取代为被氘、C1-C8烷基、苯基、萘基或联苯基取代。
4.根据权利要求3所述的化合物,其中R1为C1-C4烷基取代或未取代的C6-C10的亚芳基、C1-C4烷基取代或未取代的C2-C8的亚杂芳基;其中Ar1、R2为C1-C4烷基取代或未取代的C6-C10的芳基、C1-C4烷基取代或未取代的C1-C8的杂芳基;其中Ar2为取代或未取代的C6-C20的芳基、取代或未取代的C6-C20的杂芳基、经取代或未经取代的单环或多环C3-C20脂肪族环或芳香族环、取代或未取代的C6-C20的芳胺基;其中杂烷基或杂芳基中的一个或多个碳原子由选自O、S、N中的至少一个杂原子替换;所述取代为被氘、C1-C4烷基、苯基、萘基或联苯基取代。
6.根据权利要求1所述的化合物,其结构式如式(IV)所示:
其中R1为单键、C1-C8亚烷基、C1-C8亚杂烷基、C3-C8亚环烷基、C1-C8烷基取代或未取代的C6-C30的亚芳基、C1-C8烷基取代或未取代的C2-C28的亚杂芳基;其中R2为氢、氘、卤素、C1-C8烷基、C1-C8杂烷基、C3-C8环烷基、C1-C8烷基取代或未取代的C6-C30的芳基、C1-C8烷基取代或未取代的C1-C30的杂芳基;其中Ar1为取代或未取代的C6-C30的芳基、取代或未取代的C6-C30的杂芳基、经取代或未经取代的单环或多环C3-C30脂肪族环或芳香族环,A为取代或未取代的C6-C30的亚芳基、取代或未取代的C6-C30的亚杂芳基;其中杂烷基或杂芳基中的一个或多个碳原子由选自O、S、N、Si中的至少一个杂原子替换;所述取代为被氘、卤素、C1-C8烷基、苯基、萘基或联苯基取代。
7.根据权利要求6所述的化合物,其中R1为C1-C8烷基取代或未取代的C6-C20的亚芳基、C1-C8烷基取代或未取代的C2-C18的亚杂芳基;其中R2为C1-C8烷基、C1-C8烷基取代或未取代的C6-C20的芳基、C1-C8烷基取代或未取代的C1-C20的杂芳基;其中Ar1为取代或未取代的C6-C20的芳基、取代或未取代的C6-C20的杂芳基、经取代或未经取代的单环或多环C3-C20脂肪族环或芳香族环,A为取代或未取代的C6-C20的亚芳基、取代或未取代的C6-C20的亚杂芳基;其中杂烷基或杂芳基中的一个或多个碳原子由选自O、S、N中的至少一个杂原子替换;所述取代为被氘、C1-C8烷基、苯基、萘基或联苯基取代。
8.根据权利要求1-7任一所述的化合物,X1、X2、X3、X4独立的表示为CR0,R0独立的选自氢、C1-C8烷基。
10.权利要求1-9任一化合物在OLED器件中的应用,所述的应用为权利要求1-9任一所述的化合物作为OLED器件的光提取层材料。
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Citations (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1542083A (zh) * | 2003-02-07 | 2004-11-03 | ����Sdi��ʽ���� | 有机电致发光器件的发光化合物及用该化合物的有机电致发光器件 |
EP2067778A1 (en) * | 2007-12-03 | 2009-06-10 | Semiconductor Energy Laboratory Co., Ltd. | Quinoxaline derivative, and light emitting element, licht emitting device and electronic appliance using the same |
CN101851235A (zh) * | 2009-03-31 | 2010-10-06 | 株式会社半导体能源研究所 | 杂环化合物、使用杂环化合物的发光元件、发光装置、照明装置及电子设备 |
KR20100125004A (ko) * | 2009-05-20 | 2010-11-30 | 덕산하이메탈(주) | 3개의 카바졸을 가지는 아민 화합물 및 이를 이용한 유기전기소자, 그 단말 |
CN102070632A (zh) * | 2009-11-20 | 2011-05-25 | 中国科学院理化技术研究所 | 吡啶并咪唑衍生物及其在有机电致发光器件中的应用 |
KR20140078401A (ko) * | 2012-12-17 | 2014-06-25 | 삼성디스플레이 주식회사 | 파이렌계 화합물 및 이를 포함한 유기 발광 소자 |
WO2015001726A1 (ja) * | 2013-07-03 | 2015-01-08 | 保土谷化学工業株式会社 | 有機エレクトロルミネッセンス素子 |
KR20160001508A (ko) * | 2014-06-27 | 2016-01-06 | 희성소재 (주) | 헤테로고리 화합물 및 이를 이용한 유기발광소자 |
CN105576143A (zh) * | 2011-09-12 | 2016-05-11 | 保土谷化学工业株式会社 | 有机电致发光器件 |
US9343687B1 (en) * | 2014-12-10 | 2016-05-17 | National Chi Nan University | Imidazo[1,2-A]pyrimidine-containing compounds, method for preparing the same, and their use in electronic devices |
KR20160057018A (ko) * | 2014-11-12 | 2016-05-23 | (주)위델소재 | 아민 화합물 및 이를 이용한 유기전계 발광소자 |
KR20180061825A (ko) * | 2016-11-30 | 2018-06-08 | 엘지디스플레이 주식회사 | 유기 화합물과 이를 이용한 발광다이오드 및 유기발광다이오드 표시장치 |
CN108358932A (zh) * | 2018-02-07 | 2018-08-03 | 上海道亦化工科技有限公司 | 一种氮杂环化合物及其用途和有机电致发光器件 |
CN110845501A (zh) * | 2018-12-10 | 2020-02-28 | 广州华睿光电材料有限公司 | 一种芳胺化合物及其在有机电子器件上的应用 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111211235B (zh) * | 2018-11-22 | 2023-08-08 | 固安鼎材科技有限公司 | 有机电致发光器件 |
-
2019
- 2019-12-11 CN CN201911268938.0A patent/CN112940013B/zh active Active
-
2020
- 2020-09-19 WO PCT/CN2020/116333 patent/WO2021114801A1/zh active Application Filing
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Patent Citations (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1542083A (zh) * | 2003-02-07 | 2004-11-03 | ����Sdi��ʽ���� | 有机电致发光器件的发光化合物及用该化合物的有机电致发光器件 |
EP2067778A1 (en) * | 2007-12-03 | 2009-06-10 | Semiconductor Energy Laboratory Co., Ltd. | Quinoxaline derivative, and light emitting element, licht emitting device and electronic appliance using the same |
CN101851235A (zh) * | 2009-03-31 | 2010-10-06 | 株式会社半导体能源研究所 | 杂环化合物、使用杂环化合物的发光元件、发光装置、照明装置及电子设备 |
KR20100125004A (ko) * | 2009-05-20 | 2010-11-30 | 덕산하이메탈(주) | 3개의 카바졸을 가지는 아민 화합물 및 이를 이용한 유기전기소자, 그 단말 |
CN102070632A (zh) * | 2009-11-20 | 2011-05-25 | 中国科学院理化技术研究所 | 吡啶并咪唑衍生物及其在有机电致发光器件中的应用 |
CN105576143A (zh) * | 2011-09-12 | 2016-05-11 | 保土谷化学工业株式会社 | 有机电致发光器件 |
KR20140078401A (ko) * | 2012-12-17 | 2014-06-25 | 삼성디스플레이 주식회사 | 파이렌계 화합물 및 이를 포함한 유기 발광 소자 |
WO2015001726A1 (ja) * | 2013-07-03 | 2015-01-08 | 保土谷化学工業株式会社 | 有機エレクトロルミネッセンス素子 |
KR20160001508A (ko) * | 2014-06-27 | 2016-01-06 | 희성소재 (주) | 헤테로고리 화합물 및 이를 이용한 유기발광소자 |
KR20160057018A (ko) * | 2014-11-12 | 2016-05-23 | (주)위델소재 | 아민 화합물 및 이를 이용한 유기전계 발광소자 |
US9343687B1 (en) * | 2014-12-10 | 2016-05-17 | National Chi Nan University | Imidazo[1,2-A]pyrimidine-containing compounds, method for preparing the same, and their use in electronic devices |
KR20180061825A (ko) * | 2016-11-30 | 2018-06-08 | 엘지디스플레이 주식회사 | 유기 화합물과 이를 이용한 발광다이오드 및 유기발광다이오드 표시장치 |
CN108358932A (zh) * | 2018-02-07 | 2018-08-03 | 上海道亦化工科技有限公司 | 一种氮杂环化合物及其用途和有机电致发光器件 |
CN110845501A (zh) * | 2018-12-10 | 2020-02-28 | 广州华睿光电材料有限公司 | 一种芳胺化合物及其在有机电子器件上的应用 |
Non-Patent Citations (1)
Title |
---|
SOPHIE RÉGNIER ET AL.: "Synthesis of 3‑Aminoimidazo[1,2‑a]pyridines from α‑Aminopyridinyl Amides", vol. 81, pages 10345 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115448842A (zh) * | 2022-08-29 | 2022-12-09 | 江苏南大光电材料股份有限公司 | 联苯二胺型芳胺化合物的制备方法 |
CN115448842B (zh) * | 2022-08-29 | 2024-04-19 | 江苏南大光电材料股份有限公司 | 联苯二胺型芳胺化合物的制备方法 |
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KR20220066342A (ko) | 2022-05-24 |
CN112940013B (zh) | 2024-03-26 |
TWI752665B (zh) | 2022-01-11 |
JP2023503114A (ja) | 2023-01-26 |
TW202122398A (zh) | 2021-06-16 |
WO2021114801A1 (zh) | 2021-06-17 |
US20230063748A1 (en) | 2023-03-02 |
DE112020004795T5 (de) | 2022-06-23 |
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