CN115010619A - 一种有机发光材料及其应用 - Google Patents
一种有机发光材料及其应用 Download PDFInfo
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- CN115010619A CN115010619A CN202210624884.2A CN202210624884A CN115010619A CN 115010619 A CN115010619 A CN 115010619A CN 202210624884 A CN202210624884 A CN 202210624884A CN 115010619 A CN115010619 A CN 115010619A
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- organic light
- emitting material
- luminescent material
- organic
- organic luminescent
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- 239000000463 material Substances 0.000 title claims abstract description 55
- 238000005516 engineering process Methods 0.000 claims abstract description 11
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 238000001514 detection method Methods 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- 230000000007 visual effect Effects 0.000 claims abstract description 5
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000001769 aryl amino group Chemical group 0.000 claims abstract description 3
- 125000001174 sulfone group Chemical group 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 238000000059 patterning Methods 0.000 claims description 2
- 125000004437 phosphorous atom Chemical group 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 125000003375 sulfoxide group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 238000003384 imaging method Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 18
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 5
- 238000012984 biological imaging Methods 0.000 abstract description 3
- 238000000746 purification Methods 0.000 abstract description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- MZXOWHSTNCNYFE-UHFFFAOYSA-N [2-[2-[2-[2-[hydroxy(methyl)phosphoryl]oxyphenoxy]ethoxy]ethoxy]phenoxy]-methylphosphinic acid Chemical compound CP(O)(=O)OC1=CC=CC=C1OCCOCCOC1=CC=CC=C1OP(C)(O)=O MZXOWHSTNCNYFE-UHFFFAOYSA-N 0.000 description 14
- 239000007858 starting material Substances 0.000 description 14
- 239000013078 crystal Substances 0.000 description 12
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- 239000000843 powder Substances 0.000 description 10
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000005284 excitation Effects 0.000 description 6
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- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 238000000295 emission spectrum Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- JSEQNGYLWKBMJI-UHFFFAOYSA-N 9,9-dimethyl-10h-acridine Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3NC2=C1 JSEQNGYLWKBMJI-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000005281 excited state Effects 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- ALIQZUMMPOYCIS-UHFFFAOYSA-N benzene-1,3-disulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC(S(Cl)(=O)=O)=C1 ALIQZUMMPOYCIS-UHFFFAOYSA-N 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
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- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 238000007650 screen-printing Methods 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- BFKNIJKSZFWRDJ-UHFFFAOYSA-N CC1(C2=CC=CC=C2N(C3=CC=CC=C31)C=O)C Chemical compound CC1(C2=CC=CC=C2N(C3=CC=CC=C31)C=O)C BFKNIJKSZFWRDJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 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
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 description 2
- 235000011399 aloe vera Nutrition 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Natural products C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 description 1
- 241001116389 Aloe Species 0.000 description 1
- 235000002961 Aloe barbadensis Nutrition 0.000 description 1
- 244000186892 Aloe vera Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical group [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003609 aryl vinyl group Chemical group 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- UWCPYKQBIPYOLX-UHFFFAOYSA-N benzene-1,3,5-tricarbonyl chloride Chemical compound ClC(=O)C1=CC(C(Cl)=O)=CC(C(Cl)=O)=C1 UWCPYKQBIPYOLX-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 230000010113 energy transfer pathway Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- GWHOGODUVLQCEB-UHFFFAOYSA-N pyridine-2,6-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=N1 GWHOGODUVLQCEB-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
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- C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
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- C07C233/66—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
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- C07C233/67—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/75—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
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- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
- C07C255/60—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton at least one of the singly-bound nitrogen atoms being acylated
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
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- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/38—[b, e]-condensed with two six-membered rings
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- C07F9/46—Phosphinous acids [R2POH], [R2P(= O)H]: Thiophosphinous acids including[R2PSH]; [R2P(=S)H]; Aminophosphines [R2PNH2]; Derivatives thereof
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- C07F9/50—Organo-phosphines
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- C07F9/5337—Phosphine oxides or thioxides containing the structure -C(=X)-P(=X) or NC-P(=X) (X = O, S, Se)
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Abstract
Description
技术领域
本发明属于光电材料技术领域,具体涉及一种有机发光材料及其应用。
背景技术
具有动态响应的有机发光材料在外部刺激后,其发射颜色、强度等发生变化。这样的动态响应的特性使其在信息加密、多彩图案化、可视化检测、生物成像、有机电致发光等领域存在着丰富的应用价值。然而,大多具有动态响应的有机发光材料涉及对如光致变色化合物的改性,例如激发态质子转移类化合物、偶氮化合物、芳基乙烯类衍生物、螺吡喃类化合物等,难以避免复杂的制备方法及高昂的制备成本(e.g.Nat.Nanotechnol.2019,14,347;Adv.Funct.Mater.2019,30,1907507)。另一方面,具有动态响应的有机动态发光通过主-客体能量传递途径(e.g.Angew.Chem.Int.Ed.2020,59,16054.)实现,但存在调控复杂、需要精确的能级匹配以及相分离等缺陷。
近年来,有机发光材料的研究取得了跨越式发展,涵盖了荧光、磷光、热致延迟荧光等多种发光机制,并广泛应用于有机发光二极管(OLED)、有机发光晶体管(OLET)等领域。但根据卡莎规则,发射的波长由最低激发态决定,表现为单一固定的发射。因此,开发具有动态响应的有机发光材料是一项兼具挑战性与吸引性的工作。
发明内容
解决的技术问题:针对现有技术存在的不足,本发明提供一种有机发光材料及其应用,能有效解决上述制备成本高、调控复杂、需要精确的能级匹配以及相分离等技术问题。
技术方案:第一方面,本发明提供了一种有机发光材料,所述有机发光材料的结构通式如下式I所示:
其中,A选自羰基、砜基中的任意一种;Ar选自取代或未取代的C6~C40的芳胺基、取代或未取代的C6~C40的芳膦基中的一种;D选自C或N中的任意一种;E选自H或-A-Ar中的任意一种。
优选的,所述Ar选自以下化学结构中的一种:
R1~R6各自独立地选自氢原子、卤素、氰基、C1~C30的直链或支链烷基、C1~C30的烷氧基或C6~C30的芳香基中的一种;
R选自C1~C30的直链或支链烷基、C1~C30的直链或支链烷氧基,或C6~C30的芳香基中的一种;
a、b、e、f、h各自独立地选自0~5的整数,c、d各自独立地选自0~4的整数,g、i、j各自独立地选自0~7的整数;
X选自氮原子、磷原子、磷氧双键中的一种;
Y选自氧原子、硫原子、羰基、亚砜基、砜基中的一种;
Z选自碳原子、硅原子中的一种。
优选的,所述Ar选自以下化学结构中的一种:
优选的,所述发光材料为如下所示化学结构中的任意一种:
第二方面,本发明提供了一种第一方面所述的有机发光材料的制备方法,包括以下步骤:
(1)在氮气保护及干燥无水的条件下,在反应瓶中加入任意一种Ar基团对应的原料与碱及甲苯溶剂,在80~120℃下搅拌20~30分钟;
所述的碱为氢化钠、叔丁醇钠、碳酸钠、碳酸氢钠、三乙胺中的一种;Ar基团对应的原料与碱的摩尔比为1:1~1:4,每毫摩尔的Ar基团对应的原料加入甲苯2~8mL;
(2)向步骤(1)的反应物中,加入间苯二甲酰氯、1,3,5-均三苯甲酰氯、2,6-吡啶二甲酰氯或苯-1,3-二磺酰氯中的一种,继续反应8~12小时,反应结束后冷却至室温,调节pH值至中性;
所述间苯二甲酰氯、1,3,5-均三苯甲酰氯、2,6-吡啶二甲酰氯或苯-1,3-二磺酰氯与Ar基团对应的原料的摩尔比分别为1:1~1:2、1:1.5~1:3、1:1~1:2、1:1~1:2;
(3)用二氯甲烷与饱和食盐水萃取,用无水硫酸钠干燥,去除有机相溶剂,随后,以石油醚和二氯甲烷作为洗脱剂进行柱层析纯化,重结晶,得到相应化合物;
所述石油醚与二氯甲烷洗脱剂的体积比为1:1~1:4,柱层析所用硅胶目数为100~200目或200~300目。
第三方面,本发明提供了一种第一方面所述的有机发光材料的单晶培育方法,具体为:
采用良溶剂-不良溶剂挥发的方法,选择的良溶剂为甲苯、二氯甲烷、氯仿、四氢呋喃或乙酸乙酯中的一种,选择的不良溶剂为甲醇、乙醇、正己烷或石油醚中的一种,所述的良溶剂-不良溶剂的体积比为1:0.5~1:2。
第四方面,本发明提供了一种有机发光材料的应用,包括以下方面:
所述有机发光材料应用于信息加密技术、多彩图案化产品、可视化检测技术时,将该有机动态发光材料均匀分散在聚乙烯醇或芦荟胶等功能助剂介质中,以丝网印刷方式在滤纸或其他纸张上制备出相应的信息、图案等。
有益效果:本发明有机发光材料具有动态响应的发射特点:在溶液态下,随浓度增加,产生激基缔合物发射;在晶态粉末及单晶态下具有激发依赖和力致生色的性质,其中晶态粉末态,在可见光范围,具有随激发波长增加,主要发射峰蓝移的性质;单晶态具有“荧光-延迟荧光-室温磷光”多重发射的性质,且在不同的激发波长下,各个位置的发射峰强度的相对比例发生变化。这样的动态发光性质可用于信息加密技术、多彩图案化产品、可视化检测技术、生物成像技术和有机电致发光器件等领域。
附图说明
图1为实施例1有机发光材料DDOP(1,3-phenylenebis((9,9-dimethylacridin-10(9H)-yl)methanone))的1H NMR谱图;
图2为实施例1不同含量的有机发光材料DDOP在四氢呋喃溶液中的发射光谱图;
图3为实施例2有机发光材料DDOP的晶态粉末在不同波长处的发射光谱图;
图4为实施例2有机发光材料DDOP的晶态粉末研磨前后发射光谱图;
图5为实施例3有机发光材料DDOP用二氯甲烷/甲醇溶剂生长出的单晶在不同波长处的发射光谱图;
图6为实施例3有机发光材料DDOP用二氯甲烷/甲醇溶剂生长出的单晶在不同波长处的激发态寿命衰减图。
具体实施方式
本发明一种有机发光材料,其结构通式如式I所示,
在苯环的间位或吡啶环的2,6位引入2-3个酰化或磺酰化的Ar基生色团,
其中,A选自羰基、砜基中的任意一种;Ar为具有非平面扭曲结构的给电子基团,选自芳胺基、取代或未取代的C6~C40的芳膦基中的任意一种,具体可选择但不限于二苯胺/二苯膦及其衍生物、吩噻嗪/吩噁嗪/吖啶/吖啶酮及其衍生物;D选自碳原子或氮原子中的任意一种;E选自氢原子或-A-Ar中的任意一种。以下通过若干具体实施例对本发明做进一步说明,但实施例不限制本发明的涵盖范围。
实施例提供的一种有机发光材料是如下所示的化学结构中的任意一种:
实施例1
有机发光材料DDOP(1,3-phenylenebis((9,9-dimethylacridin-10(9H)-yl)methanone))的合成反应式,及其溶液态光物理性能:
在反应瓶中加入9,10-二氢-9,9-二甲基吖啶(1.05g,5mmol)与碳酸钠(1.38g,10mmol),抽换氮气,注入20mL重蒸及鼓泡后的甲苯溶剂,在90℃下搅拌20分钟。随后向上述反应物中,加入间苯二甲酰氯(1.02g,5mmol),继续反应8小时。反应结束后冷却至室温,调节pH值至中性,用二氯甲烷与饱和食盐水萃取,用无水硫酸钠干燥,去除有机相溶剂。然后,以体积比为1:2的石油醚和二氯甲烷作为洗脱剂进行柱层析纯化,硅胶目数为100~200目。接着用二氯甲烷和甲醇进行重结晶,得到黄色的目标产物(1.20g,产率45%)。如图1所示,经鉴证,1H NMR(400MHz,CDCl3)δ7.68(d,1H),7.47-7.52(d,4H),7.38-7.43(d,4H),7.30(d,1H),7.27(d,1H),7.18-7.25(m,3H),7.06-7.17(m,5H);13C NMR(100MHz,CDCl3)δ166.45,138.71,136.21,130.13,129.81,127.08,126.03,125.80,125.62,123.56,38.16,26.67;MALDI-TOF-MS(m/z):calcd.For C38H32N2O2,Molecular Weight:548.69。在溶液态下,随浓度增加,产生激基缔合物发射,可由图2有机发光材料DDOP的在四氢呋喃溶液中的发射光谱图证实。
实施例2
有机发光材料DDOP晶态粉末用于信息加密及多彩显示图案的制备及其晶态粉末的光物理性能:
将200mg DDOP粉末均匀分散在300mg市售芦荟胶中,搅动至混合均匀成胶状。通过丝网印刷技术在市售滤纸上印刷有机动态发光材料DDOP,其中丝网印刷模板预先设定信息及图案。由手提紫外灯照射,在254nm紫外灯照射下,可以识别出正常光下无法识别的黄绿色信息;而在254nm紫外灯照射下,可以识别出正常光下无法识别的黄蓝色信息。在320~360nm的紫外激发源照射下,印刷的图案呈现不同颜色的显示。其不同颜色的显示,说明晶态粉末具有激发依赖和力致生色的性质,均可由图3-图4在不同激发波长下和不同聚集状态下的发射光谱证实。
实施例3
有机发光材料DDOP的单晶培育及其单晶的光物理性能:
将50mg DDOP产物溶解在12mL二氯甲烷良溶剂中,再加入6mL甲醇不良溶剂,使混合溶液缓慢蒸发。最后,在溶液中形成黄色透明的块状晶体。单晶为单斜晶系,空间群为C2/c,晶胞参数为 α=90°,β=120.370(3)°,γ=90°;Z=8。其单晶的光物理性能不同于晶态粉末,具有“荧光-延迟荧光-室温磷光”多重发射的性质,可由图5-图6有机发光材料DDOP用二氯甲烷/甲醇溶剂生长出的单晶的发射光谱图和激发态寿命衰减图证实。
实施例4
有机发光材料TDOP(benzene-1,3,5-triyltris((9,9-dimethylacridin-10(9H)-yl)methanone))的合成反应式:
本实施例与实施例1制备方法基本相同,不同之处在于反应温度为100℃,反应时间为10h,碱选用叔丁醇钠,选择9,10-二氢-9,9-二甲基吖啶作为原料,且原料与1,3,5-均三苯甲酰氯的摩尔比为3:1。MALDI-TOF-MS(m/z):calcd.For C54H45N3O3,MolecularWeight:783.97。
实施例5
有机发光材料DDOPy(benzene-1,3,5-triyltris((9,9-dimethylacridin-10(9H)-yl)methanone))的合成反应式:
本实施例与实施例1制备方法基本相同,不同之处在于反应温度为120℃,反应时间为12h,碱选用氢化钠,选择9,10-二氢-9,9-二甲基吖啶作为原料,且原料与2,6-吡啶二甲酰氯的摩尔比为1:1。MALDI-TOF-MS(m/z):calcd.For C37H31N3O2,Molecular Weight:549.67。
实施例6
有机发光材料DDSOP(1,3-bis((9,9-dimethylacridin-10(9H)-yl)sulfonyl)benzene)的合成反应式:
本实施例与实施例1制备方法基本相同,不同之处在于反应温度为100℃,反应时间为12h,碱选用碳酸氢钠,选择9,10-二氢-9,9-二甲基吖啶作为原料,且原料与苯-1,3-二磺酰氯的摩尔比为1:1。MALDI-TOF-MS(m/z):calcd.For C36H32N2O4S2,Molecular Weight:620.78。
实施例7
有机发光材料DPOP(1,3-phenylenebis((10H-phenothiazin-10-yl)methanone))的合成反应式:
本实施例与实施例1制备方法基本相同,不同之处在于反应温度为80℃,反应时间为10h,碱选用三乙胺,选择吩噻嗪作为原料,且原料与间苯二甲酰氯的摩尔比为2:1。MALDI-TOF-MS(m/z):calcd.For C32H20N2O2S2,Molecular Weight:528.64。
实施例8
有机动态发光材
DPOPO(1,3-phenylenebis((5,5-dioxido-10H-phenothiazin-10-yl)methanone))的合成反应式:
本实施例与实施例1制备方法基本相同,不同之处在于反应温度为110℃,反应时间为10h,碱选用三乙胺,选择10H-phenothiazine 5,5-dioxide作为原料,且原料与间苯二甲酰氯的摩尔比为2:1。MALDI-TOF-MS(m/z),Molecular Weight:592.64。
实施例9
有机发光材料DDOSOP(1,3-bis((9,9-dimethylacridin-10(9H)-yl)sulfonyl)benzene)的合成反应式:
本实施例与实施例1制备方法基本相同,不同之处在于反应温度为95℃,反应时间为11h,碱选用碳酸钠,选择吖啶-9-(10H)-酮作为原料,且原料与苯-1,3-二磺酰氯的摩尔比为2:1。MALDI-TOF-MS(m/z),Molecular Weight:592.64。
实施例10
有机动态发光材料DDPOP(1,3-phenylenebis((9,9-diphenylacridin-10(9H)-yl)methanone))的合成反应式:
本实施例与实施例1制备方法基本相同,不同之处在于反应温度为105℃,反应时间为12h,碱选用氢化钠,选择9,9-二苯基-9,10-二氢吖啶作为原料,且原料与间苯二甲酰氯的摩尔比为2:1。MALDI-TOF-MS(m/z),Molecular Weight:796.97。
实施例11
有机发光材料1,3-phenylenebis((diphenylphosphaneyl)methanone)的合成反应式:
本实施例与实施例1制备方法基本相同,不同之处在于反应温度为115℃,反应时间为11h,碱选用氢化钠,选择二苯膦作为原料,且原料与间苯二甲酰氯的摩尔比为2:1。MALDI-TOF-MS(m/z),Molecular Weight:502.49。
实施例12
有机发光材料benzene-1,3,5-triyltris((diphenylphosphoryl)methanone)的合成反应式:
本实施例与实施例1制备方法基本相同,不同之处在于反应温度为110℃,反应时间为12h,碱选用氢化钠,选择二苯基氧化膦作为原料,且原料与1,3,5-均三苯二甲酰氯的摩尔比为3:1。MALDI-TOF-MS(m/z),Molecular Weight:762.67。
Claims (5)
5.一种如权利要求1-4任一项所述的有机发光材料在信息加密技术、多彩图案化产品、可视化检测技术、生物成像技术及有机电致发光器件中的应用。
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CN117924356A (zh) * | 2024-03-19 | 2024-04-26 | 广州佳顺科技有限公司 | 一种甲苯磺酰基二苯基磷化合物及其制备方法 |
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