CN113683555B - 一类基于联二苯衍生物受体单元的d2a型紫光有机发光材料及应用 - Google Patents
一类基于联二苯衍生物受体单元的d2a型紫光有机发光材料及应用 Download PDFInfo
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- 239000000463 material Substances 0.000 title claims abstract description 47
- KXMHPELKLKNUCC-UHFFFAOYSA-N 9-(3-carbazol-9-ylphenyl)carbazole-3-carbonitrile Chemical compound N#CC1=CC2=C(C=C1)N(C1=C2C=CC=C1)C1=CC(=CC=C1)N1C2=C(C=CC=C2)C2=C1C=CC=C2 KXMHPELKLKNUCC-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000001704 evaporation Methods 0.000 claims description 3
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- 239000011737 fluorine Substances 0.000 abstract description 2
- -1 cyano-substituted biphenyl Chemical class 0.000 abstract 2
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- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-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
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical group C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical class [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
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- 230000009286 beneficial effect Effects 0.000 description 1
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
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- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
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- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
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- 238000001906 matrix-assisted laser desorption--ionisation mass spectrometry Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
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- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
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- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
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- 230000002195 synergetic effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
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- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
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- C07D209/80—[b, c]- or [b, d]-condensed
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- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
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Abstract
本发明属于发光材料技术领域，具体涉及一类基于联二苯衍生物受体单元的D2A型紫光有机发光材料及应用。这类发光材料以含氟或氰基取代的联二苯衍生物为受体(A)单元，通过嫁接给电子(D)单元，构筑D2A型紫光有机荧光发光材料。该类结构简单、易合成、价格低廉的发光材料是一类具有开发潜力的紫光发光材料。以此类材料作为发光层的客体材料、9‑[3‑(9H咔唑‑9‑基)苯基‑9H‑咔唑‑3‑氰](mCPCN)为主体材料，制备有机电致发光器件，获得最大发射峰为396nm、CIE坐标为(0.16,0.04)、最高外量子效率为11.9％的紫光有机电致发光器件。
Description
技术领域
本发明属于发光材料技术领域，具体涉及一类基于联二苯衍生物受体单元的D2A型紫光有机发光材料及应用。
背景技术
自1987年Tang、Van Slyke等人报道了第一个有机发光二极管(OLED)器件以来，近年来，基于红、绿、蓝三基色的OLED取得了重大进展，并广泛应用于平板显示和固态照明技术(Nature,2018,563,536；Chem.Soc.Rev.,2021,50, 1030)。如今，拓宽有机发光材料的发射波长为未来OLED开辟新的应用场景，已经引起研究者的广泛兴趣，如具有紫外线(UV)发射(发射波长低于400nm) 的OLED可应用于激发光源、高密度信息存储、化学/生物传感器和杀菌消毒等，展现了潜在的开发前景。
有机热活化延迟荧光(TADF)材料主要是三重态激子通过反系间窜越(RISC) 过程转变成单重态激子，新生成的单重态激子辐射跃迁回落基态产生延迟荧光，理论上内部量子效率(IQE)可达100％，构筑的TADF材料的关键在于分子要同时满足高荧光量子产率和小的第一激发单重态与第一激发三重态能级差(Δ EST)。然而到目前为止，基于TADF的UV-OLED的电致发光(EL)性能尚不理想，大多报道的最大EQE值不超过10％(J.Mater.Chem.C2020,8,14665；Adv. Mater.2020,32,2001248)。
具有局域态(HL)和电荷转移态(CT)(简称为HLCT)杂化性质的荧光材料(Chem.Soc.Rev.,2021,50,1030；Adv.Funct.Mater.2021,2100704)，由于更高三重激发态(Tn)和最低三重态(T1)之间的能极差较大，Tn到T1之间的内转换过程受到阻碍，更多的三重态激子通过RISC过程转变为S1，进一步促进hRISC过程，而较低的局域激发态(LE)保证了短波发射，有望规避激子利用与紫外光色纯度之间的冲突，可以有效防止长寿命T1激子的积累。如2012年，马於光团队报告了首例HLCT型荧光材料TPA-PPI，固态下其最大发射峰位于434nm的深蓝色发射，获得了最大外量子效率为5.02％和CIE坐标为(0.15,0.11)的电致发光器件(Adv.Funct.Mater.,2012,22,2797-2803)；2019年，Ayse Can团队设计合成了一种新型的可溶性的低聚小分子2EHO-CNPE，其表现出典型HLCT特性，固态下其最大发射峰位于434nm的深蓝色发射，并获得最大外量子效率为7.06％和CIE坐标为(0.15,0.09)的电致发光器件，这是迄今为止最高效率的溶液处理的深蓝光HLCT荧光材料(ACSAppl.Mater.Interfaces,2019,11,44474-44486)，器件的效率仍然较低。
目前基于HLCT性质的紫外发光材料还很少报道，主要是因为UV的HLCT 材料构件极具挑战性。因此，通过构筑D-A结构单元来调节给体和受体的能级，开发出高性能的HLCT型UV有机电致发光材料来提升UV-OLED性能不仅具有挑战性，也显得尤为迫切。
发明内容
为了克服现有技术存在的不足，本发明设计了一类具有局域态和电荷转移态(HLCT)特性的有机紫光发光材料，利用HLCT的发光协同优势，实现HLCT 紫光发光材料的高效发光及其在有机电致发光二极管中的应用。
本发明提供一类含有氟或氰基取代的联二苯衍生物结构单元作为电子受体 (A)单元，弱给电子(D)单元(9,9-二甲基-9,10-吖啶、咔唑、3,6-二叔丁基咔唑、吩恶嗪、吩噻嗪、二苯并[b,e][1,4]氮杂硅烷)为D单元，构建一类 D2A型分子结构的HLCT紫光发光材料。
本发明提供的一类D2A型HLCT紫光发光材料具有式Ⅰ所示结构：
其中，X＝Y＝F；或者X＝F，Y＝CN；或者X＝CN，Y＝F。
D为式II下列基团中的任一种：
本发明提供的一类D2A型HLCT紫光发光材料具有式III所示结构
D2A型HLCT紫光发光材料优选式IIII所示结构：
本发明还提供了所述的D2A型HLCT紫光发光材料的应用，将其作为有机电致发光二极管的发光层材料，用于有机电致发光二极管。
发光层通过溶液加工或全蒸镀加工方法制备。
本发明的紫光发光的OLEDs器件的结构为：ITO/PEDOT:PSS(40nm)/mCP(30 nm)/mCPCN:HLCT UV-emitter(20-100nm)/TmPyPb(50nm)/LiF(0.8nm)/Al。
所述HLCT UV-emitter化合物掺杂的质量比为2.5-7.5％。
其中，空穴注入层为PEDOT:PSS，空穴传输层、电子阻挡层为mCP，发光层主体材料为mCPCN，电子传输层为TmPyPB，阴极层由金属铝和LiF构成,发光层为本发明优选的HLCT紫光发光材料p-CDFDB涂层。
优选的应用方法中以所述的HLCT紫光发光材料p-CDFDB制备UV-OLEDs器件的发光层，并获得了最大发射峰位于396nm，外量子效率高达11.9％的 UV-OLEDs器件。
相对于现在的技术，本发明的有益效果在于：
(1)本发明的HLCT紫光发光材料的分子结构简单、易合成、制备成本低。
(2)本发明的HLCT紫光发光材料分子内给体和受体单元之间通过苯环π桥连接，最大程度地减少了给体单元HOMO和受体单元LUMO之间的空间重叠，从而得到较小的S1-T1能量分裂(ΔEST)，促进反向系间窜跃(RISC)，实现从T1到S1态的快速跃迁，减少分子的非辐射跃迁，提高材料的发光效率。
(3)该类HLCT紫光有机发光小分子材料热稳定性高，具有优良的载流子传输性能。
(4)本发明的HLCT紫光有机发光材料可作为发光层材料，应用于UV-OLEDs 器件。本发明优选实施例实现了OLEDs器件的紫光发射，并获得了优于现有报道的外量子效率。
附图说明：
【图1】为本发明实施例1制得的化合物p-CDFDB在薄膜中和在10-5mol/L 浓度DCM溶液中的紫外可见光吸收光谱图。
【图2】为本发明实施例1制得的化合物p-CDFDB在薄膜中和在10-5mol/L 浓度DCM溶液中的光致发光光谱图。
【图3】为本发明实施例1制得的化合物p-CDFDB在不同溶剂介质下的斯托克斯位移(νa–νf)与溶剂取向极化率(f)的线性拟合图。
【图4】为本发明实施例1制得的化合物p-CDFDB固体粉末的热失重(TGA) 曲线图。
【图5】为本发明实施例1制得的化合物p-CDFDB在除氧的乙腈溶液(0.1M) 中，使用Bu4NPF6作电解质，以铂电极为工作电极，铂丝作对电极，银电极作为参比电极，二茂铁(Fc/Fc+)作内标化合物测得的循环伏安曲线图。
【图6】为本发明实施例1制得的化合物p-CDFDB的电致发光光谱图。
【图7】为本发明实施例1制得的化合物p-CDFDB以不同比例掺杂进发光层所制器件最大外量子效率-电流密度(EQE-J)曲线图。
【图8】为本发明实施例1制得的化合物p-CDFDB以不同比例掺杂进发光层所制器件的电流密度-电压-辐照度(J-V-R)曲线图。
【图9】为本发明实施例1制得的化合物p-CDFDB以不同比例掺杂进发光层所制器件的CIE坐标图。
【图10】为本发明实施例1制得的化合物SM1的核磁氢谱图。
【图11】为本发明实施例1制得的化合物SM2的核磁氢谱图。
【图12】为本发明实施例1制得的化合物p-CDFDB的核磁氢谱图。
【图13】为本发明实施例1制得的化合物p-CDFDB的核磁碳谱图。
【图14】为本发明实施例1制得的化合物p-CDFDB的质谱图。
具体实施方式
以下具体实施案例旨在对本发明进一步说明，但这些具体实施方案不以任何方式限制本发明的保护范围。
实施例1
基于D2A型HLCT紫光p-CDFDB材料合成路线如下：
分子p-CDFDB的合成步骤
化合物SM1的合成
在干燥的250mL的单口瓶中依次加入1,4-二溴-2,5-二氟苯(7.07g,26 mmol)、3,6-二叔丁基咔唑(5.59g,20mmol)、活性铜粉(1.27g,20mmol)、碘化亚铜(0.38g,2mmol)、碳酸钾(2.76g,20mmol)和100mL邻二氯苯，氮气保护和180℃下回流反应24h，停止反应，反应液呈现红褐色浑浊液。将反应液冷却至室温，抽滤，减压蒸馏滤液，用二氯甲烷(DCM)萃取(3×50m)L，萃取液水洗(3×50mL)，无水硫酸镁干燥过夜，减压旋除有机溶剂，石油醚(PE)、DCM按照体积比8：1作洗脱剂进行柱色谱分离，浓缩有机溶剂，选择三氯甲烷和甲醇(MeOH)重结晶，得到5.5g白色固体，产率57.9％。1H NMR(300MHz,CDCl3) δ8.12(s,2H),7.60(dd,J＝8.9,6.2Hz,1H),7.48(d,J＝8.6Hz,2H),7.40-7.30(m,1H),7.20-7.13(m,2H),1.46(s,18H).
化合物SM2的合成
将化合物SM1(4.70g,10mmol)、联硼酸频那醇酯(5.08g,20mmol)、1,1'- 双二苯基膦二茂铁二氯化钯(0.43g,0.60mmol)、乙酸钾(4.91g,50mmol) 和甲苯(90mL)依次加入干燥洁净的200mL的单口瓶中，混合物溶液在氮气保护下加热搅拌至120℃，回流反应24h。减压旋除甲苯，剩下的反应物固体用 DCM(每次50mL)萃取水洗三次，用无水硫酸镁干燥过夜，减压旋除有机溶剂，以体积比VPE：VDCM＝4:1作洗脱剂进行色谱分离，浓缩有机溶剂，得到的粗产物经 DCM和MeOH重结晶，得到1.99g白色粉末，产率39％。1H NMR(300MHz,CDCl3) δ8.12(s,2H),7.75-7.68(m,1H),7.47(dd,J＝8.7,1.9Hz,2H),7.31-7.26(m,1H),7.20(dd,J＝8.6,2.1Hz,2H),1.46(s,18H),1.41 (s,12H).
化合物p-CDFDB的合成
在100mL的单口瓶中依次加入SM1(1.15g，2.45mmol)、SM2(1.50g，2.94 mmol)、四(三苯基膦)钯(0.08g，0.07mmol)、2mol/L的碳酸钾溶液15mL和40mL的四氢呋喃(THF)溶剂，氮气保护下加热搅拌至75℃回流反应24h，将反应液冷却至室温，减压旋除THF溶剂，用30mLDCM萃取、饱和食盐水洗三次，合并有机相，用无水硫酸镁干燥过夜，选择VPE：VDCM＝2:1体积比的混合液作洗脱剂进行柱色谱分离，再用DCM和MeOH进行重结晶，析出白色固体1.37g，产率 72.0％。1H NMR(300MHz,CDCl3)δ8.16(d,J＝1.8Hz,4H),7.58-7.53 (m,4H),7.52-7.47(m,4H),7.31(d,J＝1.9Hz,2H),7.29(d,J＝2.0 Hz,2H),1.48(s,36H)。13C NMR(126MHz,CDCl3)δ156.68,154.88,154.69, 152.88,143.81,138.71,124.00,123.93,119.60,119.41,116.49,109.46, 34.83,32.03。MALDI-MS(m/z):calcd.781.00found.780.53.
实施例2
测试实施例1中的化合物p-CDFDB薄膜的紫外可见吸收光谱，由图1可知，化合物p-CDFDB在溶液中的紫外可见吸收光谱大致有三种吸收峰：短波长(＜300 nm)处的吸收峰归属于分子内的π-π*和n-π*的跃迁吸收；长波长(305-380nm) 处的吸收峰归属于分子内给体单元到受体单元的电荷转移(ICT)跃迁吸收峰。
实施例3
将实施例1的化合物p-CDFDB溶解在DCM中配成10-5mol/L标准浓度溶液，测试其溶液的紫外可见吸收光谱。由图1可知，化合物p-CDFDB在溶液中的紫外可见吸收光谱的峰型与在薄膜中大致相同，在220-270nm短波长处出现的强跃迁吸收峰归属于分子的π-π*跃迁吸收，在270-305nm处出现的吸收峰归属于分子内n-π*跃迁，在305-385nm处出现的弱吸收峰归属于分子给体单元到受体单元的ICT吸收峰。
实施例4
测试实施例1中化合物p-CDFDB在薄膜及其在10-5mol/L DCM溶液下的光致发光性能。由图2所示，在固定波长的单色光源激发下，化合物p-CDFDB在薄膜中从约370nm处出现发射峰，最大发射峰为405nm，在紫光区域。化合物 p-CDFDB在溶液中的发射峰起峰位置与在薄膜中大致一样，但由于溶剂化效应，最大发射峰稍有红移，约为430nm。
实施例5
将实施例1的化合物p-CDFDB溶解在不同极性的溶剂中，配制成10-5mol/L 标准浓度溶液，分别测试其在不同溶剂中的紫外可见吸收光谱、光致发光光谱，并计算化合物p-CDFDB在不同极性溶剂中的斯托克斯位移(νa–νf)，绘制化合物p-CDFDB在低极性溶液和高极性溶剂中的斯托克斯位移与溶剂取向极化率(f) 的线性拟合图。如图3所示，化合物p-CDFDB在低极性溶剂与高极性溶剂中的斯托克斯位移-溶剂取向极化率明显呈两段线性关系，这是由CT态分子的偶极矩对溶剂极性的敏感性造成。因此，分子在低极性溶剂中激发态以LE态为主，偶极矩减小，而在高极性溶剂中激发态以CT态为主，偶极矩明显增大，证实了其激发态具有明显的HLCT特性。
实施例6
对实施例1中制得的化合物p-CDFDB进行了热稳定性能测试。在氮气氛围下，以10℃/min的升温速率从室温加热到500℃，进行热失重测试。如图4所示，化合物p-CDFDB失重5％的温度为205℃，表明材料具有良好的热稳定性能，为材料后续作为发光层进行溶液加工、全蒸镀器件的制备奠定了基础。
实施例7
实施例1中的化合物p-CDFDB的电化学性能测试条件如下：制得的化合物 p-CDFDB在除氧的乙腈溶液(0.1M)中，使用Bu4NPF6作电解质，以铂电极为工作电极，铂丝作对电极，银电极作为参比电极，二茂铁(Fc/Fc+)作内标化合物进行测试。如图5所示，化合物p-CDFDB在0-1.2V区间内呈现出不可逆的氧化峰，根据经验公式可以计算出，化合物p-CDFDB的HOMO能级为-5.84eV。结合化合物p-CDFDB纯膜的紫外吸收光谱起峰位置，可以计算出化合物p-CDFDB的带隙 (Eg)为3.23eV，因此可以计算出LUMO为-2.61eV。
实施例8
在装有积分球的瞬态荧光光度计中完成基于实施例1中化合物p-CDFDB的光致发光量子效率(PLQY)的测试，测试方法如下：将化合物p-CDFDB溶于二氯甲烷溶剂中配成浓度在10mg/ml左右的溶液，固定石英片在匀胶机上，调整匀胶机转速为1500r/min，通过移液枪快速滴加80μl溶液至石英片中心，在室温下甩膜30s，制成样品薄膜。先后测试空白石英片和样品薄膜的荧光强度。通过软件计算得到化合物p-CDFDB的荧光量子效率(PLQY)为56.0％。
实施例9
实施例1中的化合物p-CDFDB在有机电致发光器件中的应用：以化合物 p-CDFDB作为器件发光层掺杂剂制备结构为ITO/PEDOT:PSS(40nm)/MCP(30 nm)/mCPCN:化合物p-CDFDB(25nm)/TmPyPb(50nm)/LiF(0.8nm)/Al的有机电致发光二极管。其中，PEDOT:PSS为空穴注入层，mCPCN为发光层主体材料，化合物p-CDFDB为发光层客体材料，TmPyPB为电子传输层，CsF/Al为阴极。通过研究化合物p-CDFDB的掺杂比例，发现化合物p-CDFDB的掺杂比例为2.5％时器件性能最优：由于仪器限制，在测试实例1中化合物p-CDFDB不同掺杂浓度的电致发光光谱时未能采集其完整光谱，但由图6所示，化合物p-CDFDB的最大发射峰为396nm，达到紫光区域。如图7所示，最大外量子效率为11.9％。由图8所示，器件的最大辐照度为500mW/Sr/m2。如图9所示，器件的CIE坐标为(0.16,0.04)。
尽管结合了优选实施例对本发明进行了说明，但本发明并不局限于上述实施例，应当理解所附权利要求概括了本发明的范围。在本发明构思的指导下，本领域的技术人员应当意识到，对本发明的各实施例方案所进行的一定的改变，都将被本发明的权利要求书的精神和范围所覆盖。
Claims (5)
1.一类基于联二苯衍生物受体单元的D2A型紫光有机发光材料，其特征在于，所述有机发光材料的结构式如下:
。
2.一种根据权利要求1所述的D2A型紫光有机发光材料的应用，其特征在于，将所述紫光有机材料作为发光层材料，应用于紫光有机电致发光二极管的发光层。
3.根据权利要求2所述的应用，其特征在于，所述发光层通过溶液加工或全蒸镀加工方法制备。
4.根据权利要求2所述的应用，其特征在于，所述的紫光有机电致发光二极管的器件的结构为ITO/PEDOT:PSS 40 nm/mCP 30 nm/mCPCN: 紫光有机材料20-100 nm/TmPyPb 50nm/LiF 0.8 nm/Al。
5.根据权利要求4所述的应用，其特征在于，所述紫光有机材料掺杂的质量比为2.5-7.5%。
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