CN112480088A - 一种热激活延迟荧光型共价有机框架材料 - Google Patents
一种热激活延迟荧光型共价有机框架材料 Download PDFInfo
- Publication number
- CN112480088A CN112480088A CN202011358242.XA CN202011358242A CN112480088A CN 112480088 A CN112480088 A CN 112480088A CN 202011358242 A CN202011358242 A CN 202011358242A CN 112480088 A CN112480088 A CN 112480088A
- Authority
- CN
- China
- Prior art keywords
- delayed fluorescence
- organic framework
- framework material
- covalent organic
- general formula
- 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
- 239000000463 material Substances 0.000 title claims abstract description 39
- 239000013310 covalent-organic framework Substances 0.000 title claims abstract description 29
- 230000003111 delayed effect Effects 0.000 title claims abstract description 24
- 238000007725 thermal activation Methods 0.000 title claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- 238000003786 synthesis reaction Methods 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 6
- -1 triazine ring compound Chemical class 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000003172 aldehyde group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 238000011161 development Methods 0.000 claims description 3
- 229910001385 heavy metal Inorganic materials 0.000 claims description 3
- 239000007777 multifunctional material Substances 0.000 claims description 3
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 claims description 3
- 238000013461 design Methods 0.000 abstract description 4
- 230000005281 excited state Effects 0.000 abstract description 4
- 239000011148 porous material Substances 0.000 abstract description 4
- 230000000171 quenching effect Effects 0.000 abstract description 4
- 230000007704 transition Effects 0.000 abstract description 4
- 238000004020 luminiscence type Methods 0.000 abstract description 3
- 238000010791 quenching Methods 0.000 abstract description 3
- 239000002131 composite material Substances 0.000 abstract description 2
- 238000005401 electroluminescence Methods 0.000 abstract description 2
- 125000001841 imino group Chemical class [H]N=* 0.000 abstract 1
- 239000013384 organic framework Substances 0.000 abstract 1
- 230000035939 shock Effects 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000002441 reversible effect Effects 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- LNHGLSRCOBIHNV-UHFFFAOYSA-N 4-[tris(4-aminophenyl)methyl]aniline Chemical compound C1=CC(N)=CC=C1C(C=1C=CC(N)=CC=1)(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 LNHGLSRCOBIHNV-UHFFFAOYSA-N 0.000 description 2
- VHJCTDHAJKNLIM-UHFFFAOYSA-N 4-tris(4-aminophenyl)silylaniline Chemical compound C1=CC(N)=CC=C1[Si](C=1C=CC(N)=CC=1)(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 VHJCTDHAJKNLIM-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 150000004984 aromatic diamines Chemical class 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 230000009878 intermolecular interaction Effects 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- OULOEJYWPDLJJI-UHFFFAOYSA-N acridine-1-carbaldehyde Chemical compound C1=CC=C2C=C3C(C=O)=CC=CC3=NC2=C1 OULOEJYWPDLJJI-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
- 238000006757 chemical reactions by type Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000002715 modification method Methods 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- PFXVKGGZWQQTSE-UHFFFAOYSA-N sulfuryl dicyanide Chemical compound N#CS(=O)(=O)C#N PFXVKGGZWQQTSE-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
Classifications
-
- 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
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon 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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
- C07F7/083—Syntheses without formation of a Si-C bond
-
- 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
-
- 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
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
-
- 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
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
本发明提供一种热激活延迟荧光型共价有机框架材料,合成了一系列含亚氨基的延迟荧光的COF分子。这类分子由于含有多个芳环,并且节点由不饱和C=N键连接,刚性离域大π键结构的使其具有本征的发光的属性;COFs较大的孔道尺寸可以为特殊离子的引入提供空间需求,从而形成多功能复合材料;COF分子的刚性结构可以有效避免TADF分子的震动淬灭,防止激发态畸变引起的能量损失。TADF材料可以同时利用单重态激子和三重态激子发光;当单重态和三重态的能级差较(ΔEST)小时,三重态激子可以被热激活成单重态激子,最终以辐射跃迁的方式实现延迟荧光;因此,TADF型COFs的电致发光的内部量子效率理论上限为100%,同时由于刚性的分子结构,可以有效的避免分子振动和转动引起的激子弛豫和能量泄露;本发明将TADF性质引入COFs的分子设计中以实现热激活延迟荧光型供价有机框架材料。
Description
技术领域
本发明具体涉及一种热激活延迟荧光共价有机框架材料分子设计和制备方法,属于化合物技术领域。
背景技术
共价有机框架材料有着较小的密度和稳健的结构,选择功能化的结构单元以可逆的方式连接,通过热力学的调控使其具有良好的结构和缺陷修复能力以及长程有序的高晶度。二维COFs通过共价键连接成片层,层层的堆积就形成了周期性的刚性骨架和开放的孔道结构。特殊功能性的材料可以被固定在这种刚性结构中,平面共轭的刚性和开放的孔道结构能游戏促进载流子的传输。此外,长程的结晶度可以避免电荷载体的重组,防止其碰撞失活从而延长激发态寿命。将光电小分子作为COFs的功能结构基元直接引入或者通过后修饰的方法加到刚性骨架上可以大大提高了光子吸收率和电子传输率。含大π共轭结构的COF材料由于电子离域性诱导的激子跃迁使得材料具有较强的荧光性。
热激活延迟荧光(TADF)具有理论上100%的激子利用率,在单重态和三重态具有较小能极差时,通常反向系间窜越(RISC)实现三重态到单重态的能量转换。较小的ΔEST需要从空间上分离HOMO和LOMO的轨道重叠,给体-受体型的TADF材料具有分子内电荷转移的特性,这与分离的前线轨道能级想矛盾。在经典的TADF分子设计中,HOMO和LOMO分别位于电子给体和电子受体上,使得材料的轨道能级易于分离。由于较小的能极差,利用延迟荧光材料作为发射层的有机发光二极管,电荷可以有效的从电子传输层中注入发光层,从而降低器件的驱动电压,从而提高功率效率。要提高TADF材料的电致发光效率,必须抑制单重态激子的非辐射跃迁和三重态激子的浓度猝灭效应。TADF材料分子设计中,对于给体基团,可以采用咔唑、吖啶、吩噁嗪等衍生物;受体基团可以是氰基、砜基、三嗪、吡啶、羰基、嘧啶等衍生物。此外,引入扭曲构象或饱和体系可以保持TADF材料具有较高的三重态能量,从而避免能量泄漏。
发明内容
本发明的目的是为了解决上述问题,提出一种热激活延迟荧光型共价有机框架材料。
为了实现上述目的,本发明采用的技术方案如下:
一种热激活延迟荧光型共价有机框架材料,具有以下具体合成通式:
优选地,这种材料具有无重金属结构、100%的理论内部量子效率、反应条件简单温和易于制备、受热力学控制且产品收率和纯度较高等优点,是一种极具发展前景的高效、大规模、低成本的多功能材料。
本发明有以下优点和效果:
有机光电材料经历了荧光材料、磷光材料和延迟荧光材料三代,延迟荧光源自激发三重态通过反向系间窜越重新生成激发单线态的辐射跃迁。与之前两代材料相比,TADF材料在不含贵金属的情况下能同时利用单重态激子和三重态激子实现发光。当单重态和三重态能量差较小时,三重态激子可以被热激活成单重态激子产生延迟荧光,而内部量子效率理论上限为100%,延迟荧光寿命可以达到微秒甚至毫秒级别。然而,延迟荧光材料都具有浓度猝灭的现象。要获得高效的发光效率,必须有效的限制激发态下分子的振动、转动以及分子间相互作用。
共价有机框架材料是一种由共价键将刚性有机构筑单元结合的新型多孔的晶体材料,具有多孔性、大比表面积等特性。具有荧光性能的有机单元通过动态共价平衡来构成荧光COF的分子,这类分子由于含有多个苯环作为构筑单元,并且节点由不饱和C=N键连接,所以该大共轭体系表现出大的刚性使其具有本征发光的属性。将TADF分子作为COFs的构筑骨架,一方面可以利用TADF的高效荧光性质提高COF材料的发光性能。另一方面,COF的刚性结构可以有效的固定TADF分子,避免激发态振动弛豫和分子间相互作用引起的激子猝灭。席夫碱反应基于醛或酮与伯胺在特定的条件下脱水缩合形成亚胺键,基于此种反应条件简单、产品收率较高是目前COFs合成中较常见的反应类型。另外,COF材料较大的孔道尺寸可以引入多种官能团,从而构成多功能复合材料。
具体实施方式
下面结合实施例对本发明做进一步的说明:
一种有机电致发光材料,该材料具体是一种热激活延迟荧光多孔聚合物材料,具有一下具体合成通式:
这种材料具有无重金属结构、100%的理论内部量子效率、反应条件简单温和易于制备、受热力学控制且产品收率和纯度较高等优点,是一种极具发展前景的高效、大规模、低成本的多功能材料。
优选地,上述的热激活延迟荧光材料为具有如下结构的化合物:
实施例1
合成C1在回流条件下,将三嗪咔唑醛(558mg,0.5mmol)与对二苯胺(432mg,4mmol)在20mL乙醇、2mL二氧六环和0.3mL乙酸水溶液中反应24h合成该化合物。然后将溶液冷却至室温,通过过滤收集沉淀,用乙醇洗涤以去除多余的对苯二胺,并在真空下干燥以得到淡黄色固体。
实施例2
合成C2在回流条件下,将三嗪吖啶醛(622mg,0.5mmol)与4,4'-二氨基联苯(736mg,4mmol)在20mL乙醇、2mL二氧六环和0.3mL乙酸水溶液中反应24h合成该化合物。然后将溶液冷却至室温,通过过滤收集沉淀,用乙醇洗涤以去除多余的4,4'-二氨基联苯,并在真空下干燥以得到淡黄色固体。
实施例3
合成C3在回流条件下,将三嗪苯胺醛(561mg,0.5mmol)与1,3,5-三苯胺(492mg,4mmol)在20mL乙醇、2mL二氧六环和0.3mL乙酸水溶液中反应24h合成该化合物。然后将溶液冷却至室温,通过过滤收集沉淀,用乙醇洗涤以去除多余的1,3,5-三苯胺,并在真空下干燥以得到淡黄色固体。
实施例4
合成C2在回流条件下,将三嗪吩噁嗪醛(582mg,0.5mmol)与1,3,5-(三苯胺基)苯(1404mg,4mmol)在20mL乙醇、2mL二氧六环和0.3mL乙酸水溶液中反应24h合成该化合物。然后将溶液冷却至室温,通过过滤收集沉淀,用乙醇洗涤以去除多余的4,4'-二氨基联苯,并在真空下干燥以得到淡黄色固体。
实施例5
合成C5在回流条件下,将三嗪噻吩嗪醛(606mg,0.5mmol)与四(4-氨基苯基)甲烷(1520mg,4mmol)在20mL乙醇、2mL二氧六环和0.3mL乙酸水溶液中反应24h合成该化合物。然后将溶液冷却至室温,通过过滤收集沉淀,用乙醇洗涤以去除多余的四(4-氨基苯基)甲烷,并在真空下干燥以得到淡黄色固体。
实施例6
合成C6在回流条件下,将三嗪吩噁嗪醛(582mg,0.5mmol)与四(4-氨基苯基)硅(1584mg,4mmol)在20mL乙醇、2mL二氧六环和0.3mL乙酸水溶液中反应24h合成该化合物。然后将溶液冷却至室温,通过过滤收集沉淀,用乙醇洗涤以去除多余的四(4-氨基苯基)硅,并在真空下干燥以得到淡黄色固体。
以上所述均为本发明的优选实施方式,对于本技术领域的普通技术人员,在不脱离本发明的原理前提下,对本发明的各种等价形式的修改均属于本申请所附权利要求的保护范围。
Claims (6)
6.一种热激活延迟荧光型共价有机框架材料的应用,其特征在于:这种材料具有无重金属结构、100%的理论内部量子效率、反应条件简单温和易于制备、受热力学控制且产品收率和纯度较高等优点,是一种极具发展前景的高效、大规模、低成本的多功能材料。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202011358242.XA CN112480088A (zh) | 2020-11-27 | 2020-11-27 | 一种热激活延迟荧光型共价有机框架材料 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202011358242.XA CN112480088A (zh) | 2020-11-27 | 2020-11-27 | 一种热激活延迟荧光型共价有机框架材料 |
Publications (1)
Publication Number | Publication Date |
---|---|
CN112480088A true CN112480088A (zh) | 2021-03-12 |
Family
ID=74936221
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202011358242.XA Pending CN112480088A (zh) | 2020-11-27 | 2020-11-27 | 一种热激活延迟荧光型共价有机框架材料 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN112480088A (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113512033A (zh) * | 2021-05-19 | 2021-10-19 | 南京工业大学 | 吩噁嗪和吩噻嗪共价三嗪框架材料及其制备方法与应用 |
CN114957578A (zh) * | 2022-06-21 | 2022-08-30 | 南京理工大学 | 基于噻吩嗪基的共价有机框架材料及其制备方法和应用 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2832767A1 (en) * | 2013-07-31 | 2015-02-04 | Fundación Imdea Nanociencia | Method for the Synthesis of Covalent Organic Frameworks |
CN106967216A (zh) * | 2017-04-18 | 2017-07-21 | 吉林大学 | 一种亚胺联接的共价有机骨架材料及其制备方法与应用 |
CN111808282A (zh) * | 2020-08-03 | 2020-10-23 | 中国地质大学(北京) | 低温快速制备二维共价有机框架材料的方法及二维共价有机框架材料 |
-
2020
- 2020-11-27 CN CN202011358242.XA patent/CN112480088A/zh active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2832767A1 (en) * | 2013-07-31 | 2015-02-04 | Fundación Imdea Nanociencia | Method for the Synthesis of Covalent Organic Frameworks |
CN106967216A (zh) * | 2017-04-18 | 2017-07-21 | 吉林大学 | 一种亚胺联接的共价有机骨架材料及其制备方法与应用 |
CN111808282A (zh) * | 2020-08-03 | 2020-10-23 | 中国地质大学(北京) | 低温快速制备二维共价有机框架材料的方法及二维共价有机框架材料 |
Non-Patent Citations (1)
Title |
---|
胡彬等: "具有双极性端枝的3D结构化合物的合成及光学性能" * |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113512033A (zh) * | 2021-05-19 | 2021-10-19 | 南京工业大学 | 吩噁嗪和吩噻嗪共价三嗪框架材料及其制备方法与应用 |
CN114957578A (zh) * | 2022-06-21 | 2022-08-30 | 南京理工大学 | 基于噻吩嗪基的共价有机框架材料及其制备方法和应用 |
CN114957578B (zh) * | 2022-06-21 | 2024-03-19 | 南京理工大学 | 基于噻吩嗪基的共价有机框架材料及其制备方法和应用 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Jiang et al. | A review on synthesis of carbazole-based chromophores as organic light-emitting materials | |
CN111574544A (zh) | 一种含硼的有机化合物及其在有机电致发光器件上的应用 | |
CN107880027B (zh) | 一种以三嗪为核心的化合物及其在有机电致发光器件上的应用 | |
CN112480088A (zh) | 一种热激活延迟荧光型共价有机框架材料 | |
JP7222173B2 (ja) | 有機発光素子 | |
CN108948095B (zh) | 基于苯基咔唑的四齿环金属铂配合物及其应用 | |
CN110317140B (zh) | 一种以芳胺接双二甲基芴为核心的化合物及其应用 | |
CN113603628B (zh) | 一种非共轭连接的空间电荷转移热活化延迟荧光材料及其电致发光应用 | |
CN107880030B (zh) | 以三嗪为核心的化合物及有机电致发光器件 | |
CN110526825B (zh) | 一种以异屈与三芳胺结构为核心的化合物及其应用 | |
CN110885338A (zh) | 一种以三芳胺为核心的有机化合物及其制备方法和其应用 | |
CN103739607A (zh) | 一种基于三并咔唑多臂结构红光材料及其制备方法与应用 | |
CN110092800B (zh) | 热活化延迟荧光分子材料及其合成方法、电致发光器件 | |
CN107880028B (zh) | 一种以氮杂苯为核心的化合物及有机电致发光器件 | |
CN113416190B (zh) | 基于吡唑并[2,3-f][1,10]菲啰啉-2,3-二腈的有机电致发光材料及应用 | |
CN112961157A (zh) | 一种基于吲哚并咔唑的有机发光材料及其制备方法和应用 | |
CN110655486A (zh) | 一种以二苯并环庚烯为核心的化合物及其应用 | |
CN113979903B (zh) | 一种含有苯基砜-螺芴结构单元的有机热活化延迟荧光材料、制备方法及应用 | |
WO2023193596A1 (zh) | 金属铂(ii)和钯(ii)配合物、有机发光器件及显示或照明装置 | |
CN110759935B (zh) | 基于氟硼络合物的蓝色热活性延迟荧光材料及其应用 | |
CN108409794B (zh) | 基于苯基-咔唑的四齿环金属铂配合物及其应用 | |
CN107827873B (zh) | 一种三芳胺类衍生物及其有机发光器件 | |
CN115557881A (zh) | 一种有机小分子空穴传输材料、合成方法及其应用 | |
KR20200050675A (ko) | 유기전자소자용 화합물, 이를 포함하는 유기전자소자 및 유기전자소자를 포함하는 표시장치 | |
CN110862290A (zh) | 一种含有蒽烯结构化合物及其在有机电致发光器件的应用 |
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 |