CN108264477A - 应用于有机发光二极管的主体材料 - Google Patents
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- 239000000463 material Substances 0.000 title claims abstract description 34
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 239000000460 chlorine Substances 0.000 claims abstract description 14
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000001424 substituent group Chemical group 0.000 claims abstract description 10
- 238000006467 substitution reaction Methods 0.000 claims abstract description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 7
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 7
- 239000011737 fluorine Substances 0.000 claims abstract description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 5
- 239000011630 iodine Substances 0.000 claims abstract description 5
- -1 Hydrogen Chemical class 0.000 claims abstract description 4
- 238000006579 Tsuji-Trost allylation reaction Methods 0.000 claims abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 238000005401 electroluminescence Methods 0.000 claims description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000003944 tolyl group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims 1
- 230000005611 electricity Effects 0.000 claims 1
- 230000005669 field effect Effects 0.000 claims 1
- 230000009477 glass transition Effects 0.000 abstract description 12
- 239000010410 layer Substances 0.000 description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 230000005540 biological transmission Effects 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 230000027756 respiratory electron transport chain Effects 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
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- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
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- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
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- UTEFBSAVJNEPTR-RGEXLXHISA-N loprazolam Chemical compound C1CN(C)CCN1\C=C/1C(=O)N2C3=CC=C([N+]([O-])=O)C=C3C(C=3C(=CC=CC=3)Cl)=NCC2=N\1 UTEFBSAVJNEPTR-RGEXLXHISA-N 0.000 description 1
- 229960003019 loprazolam Drugs 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen 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
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
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- 239000004065 semiconductor Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
Classifications
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- 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
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- 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
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- 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
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
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Abstract
本发明涉及应用于有机发光二极管的主体材料，具有式(I)所述的结构，其中，其中，R、R2独立选自氢，C1‑C4烷基取代或未取代的C1‑C4烷基，C1‑C4烷基取代或者未取代的C2‑C4烯烷基，C1‑C4烷基取代或者未取代的C2‑C4炔烷基，C6‑C10的含有一个或者多个取代基R1取代或未取代的芳基、芳烃基，C5‑C8的含有一个或者多个取代基R1取代或未取代的含有一个或者多个杂原子的杂芳基，R1独立选自氟F，氯Cl，溴Br，碘I，氰基CN，C1‑C4的烷基；Ar为N‑芳基咔唑。实验结果表明，本发明的有机主体材料具有高玻璃化转变温度，热稳定性高，所制备的有机发光器件性能良好且稳定。
Description
技术领域
本发明涉及新型有机发光二极管主体材料，通过真空沉积成薄膜，作为发光层材料用于有机发光二极管器件。
背景技术
近年来，有机发光二极管(OLED)作为一种有巨大应用前景的照明、显示技术，受到了学术界与产业界的广泛关注。OLED器件具有自发光、广视角、反应时间短及可制备大面积和柔性器件等特性，而且其还具有潜在的低成本优势，使其成为下一代显示、照明技术的有力竞争者。基于这些特性，OLED也被誉为21世纪明星显示产品。如今，OLED显示产品已经实现了商业化。但仍然存在效率低、寿命短等问题，有待人们进一步研究。
有机发光二极管为电致发光器件，在电压驱动下，电子和空穴分别经电子传输层和空穴传输层进入发光层复合形成激子；激子将能量传递给有发光特性的有机分子，使其受激发，激发态分子回到基态时发生辐射跃迁而发光。自1998年Forrest等人报道了电致磷光发光器件(PHOLED)以来，PHOLED因其可以利用三线态和单线态激子发光而实现100％内量子效率而备受关注。PHOLED器件通常采用多层结构，其优点在于可以方便地调节载流子注入、传输及复合等过程。在发光层中，当客体掺杂浓度较高时，会出现浓度淬灭和T1-T1湮灭，导致发光效率降低。为了解决这些问题，通常将客体材料掺杂在主体材料中，从而“稀释”客体材料的浓度。理想的主体材料应具有合适的前线轨道能级以实现主客体间有效地能量转移，良好的载流子传输性能以便在发光层中实现电子和空穴的平衡，和较好的热稳定性以利于形成稳定的非晶态薄膜。因此，为了获得高效PHOLED器件，开发新型主体材料尤为重要。
目前，广泛使用的主体材料为具有对称结构的4,4'-N,N'-二咔唑联苯(CBP)，就其光电性能而言基本上符合OLED对主体材料的要求，但其玻璃化转变温度较低，仅为62℃，因此CBP具有容易结晶的缺点。有机层材料一旦结晶，会使得分子间的电荷跃迁机制与正常非晶态薄膜机制不相同，能量转移方式也会发生变化。最终导致主客体间不能有效地进行能量转移，降低器件的使用寿命。非晶薄膜向晶态薄膜的转变难易程度主要受有机材料的玻璃化转变温度(Tg)影响，玻璃化转变温度越高，则薄膜的稳定性越好。因此，开发新型高玻璃化转变温度主体材料十分必要。
CBP对称的分子结构
发明内容
针对上述材料的缺陷，本发明提供一种可应用在有机电致发光器件上的高形态稳定性的有机主体材料。
应用于有机发光二极管的主体材料，具有化学式(I)的结构：
Ar为下列基团中的一个：
其中，R、R2独立选自氢，C1-C4烷基取代或未取代的C1-C4烷基，C1-C4烷基取代或者未取代的C2-C4烯烷基，C1-C4烷基取代或者未取代的C2-C4炔烷基，C6-C10的含有一个或者多个取代基R1取代或未取代的芳基、芳烃基，C5-C8的含有一个或者多个取代基R1取代或未取代的含有一个或者多个杂原子的杂芳基；
R1独立选自氟F，氯Cl，溴Br，碘I，氰基CN，C1-C4的烷基。
优选地，R、R2独立选自氢，C1-C4烷基，C6-C10的含有一个或者多个取代基R1取代或未取代的芳基、芳烃基；
R1独立选自氟F，氯Cl，溴Br，碘I，C1-C4的烷基。
更优选地，R选自氢，甲基，叔丁基，苯基，甲苯基，萘基；
R2独立选自氢H，C1-C4烷基，C6-C10的含有一个或者多个取代基R1取代或未取代的芳基、芳烃基；
R1独立选自氟F，氯Cl，溴Br，C1-C4的烷基。
进一步优选：R、R2选自氢，叔丁基，苯基，甲苯基，R1选自氢、甲基。
特别优选：R、R2选自氢，叔丁基，苯基，R1选自氢。
有机电致发光二极管器件，包括阴极、阳极和有机层，所述有机层为空穴传输层、发光层、空穴阻挡层、电子传输层中的一层或多层。需要特别指出，这些有机层不必每层都存在。
所述空穴传输层、空穴阻挡层、发光层和/或电子传输层中含有式(I)所述的化合物。
所述式(I)所述的化合物为应用于发光层中的主体材料。
本发明的电子器件有机层的总厚度为1-1000nm，优选1-500nm，更优选5-300nm。
所述有机层可以通过蒸渡或溶液法形成薄膜。
如上面提到的，本发明的式(I)所述的化合物如下，但不限于所列举的结构：
再优选：式(I)所表示化合物为以下结构
器件实验表明，本发明的有机主体材料具有高玻璃化转变温度，热稳定性高，所制备的有机电致发光器件性能良好且稳定，有潜力应用于有机电致发光器件领域。
附图说明
图1为本发明化合物1的DSC曲线，
图2为本发明的有机电致发光器件结构图，
其中10代表为玻璃基板，20代表为阳极，30代表为空穴注入层，40代表为空穴传输层，50代表发光层，60代表空穴阻挡层，70代表电子传输层，80代表电子注入层，90代表为阴极。
具体实施方式
为了更详细叙述本发明，特举以下例子，但是不限于此。
实施例1
化合物1的合成路线
化合物b的合成
氮气保护下，将五氧化二磷(0.8g,5.6mmol)加入甲烷磺酸(9.2g,95.6mmol)中，室温搅拌2h，使其充分溶解，呈粘稠状油状物(伊顿试剂)。随后，将伊顿试剂(1mL)逐滴加入化合物a(3.2g,10.0mmol)(参考文献J.Mater.Chem.C.,2(12),2160-2168合成)和三苯甲醇(2.86g，11.0mmol)的二氯甲烷(100mL)中。滴加完毕后，室温下搅拌2h。反应液水洗三次，无水硫酸钠干燥。减压除去溶剂后，粗产物经重结晶得白色固体(4.2g,产率74.4％)。1H NMR(400MHz，CDCl3,δ):8.01(s,1H),7.94(d,J＝7.6Hz,1H),7.69(d,J＝8.8Hz,2H),7.44(d,J＝8.8,2H),7.36(d,J＝3.6Hz,2H),7.32–7.18(m,18H).
化合物1的合成
将化合物b(2.0g,3.5mmol)、化合物c(1.44g,3.9mmol)(参考文献J.Mater.Chem.C.,1(24),3871-3878合成)、Pd(PPh3)4(208mg,0.2mmol)、四氢呋喃(30mL)和碳酸钾水溶液(2M,5mL)依次加入Schlenk管中。抽真空，通入氮气，反复进行三次。氮气保护下，回流过夜。冷至室温后，将上述反应液加入水中，经二氯甲烷萃取三次，合并有机相。有机相经无水硫酸钠干燥后，减压蒸除溶剂，剩余物经柱层析分离得白色固体(2.1g,产率81.6％),升华后纯度为99.8％。1H NMR(400MHz,CDCl3,δ):8.17(d,J＝8.0Hz,2H),8.05(s,1H),7.98(d,J＝7.6Hz,1H),7.90-7.87(m,4H),7.72-7.69(m,4H),7.52(s,1H),7.50(s,2H),7.46-7.38(m,4H),7.34-7.19(m,19H)。玻璃化转变温度为159℃。
实施例2
玻璃化转变温度测试：
在氮气保护下，以20℃/min的加热和冷却速率用示差扫描量热法(DSC)测试化合物1的玻璃化转变温度(图1)。测得化合物1的玻璃化转变温度Tg为159℃。而文献所报道的CBP的玻璃化转变温度仅为62℃。
可见，本发明中的化合物比常用市售材料CBP具有更高的玻璃化转变温度，本发明显著提高了电致发光器件材料的热稳定性，更符合电致发光器件对有机材料的要求。
实施例3
有机电致发光器件1的制备
使用本发明的有机主体材料制备OLED，见图2
首先，将透明导电ITO玻璃基板10(上面带有阳极20)依次经：洗涤剂溶液和去离子水，乙醇，丙酮，去离子水洗净，再用氧等离子处理30秒。
然后，在ITO上蒸渡10nm厚的MoO3作为空穴注入层30。
然后，蒸渡化合物NPB,形成40nm厚的空穴传输层40。
然后，在空穴传输层上蒸渡30nm厚的Ir(PPy)3(9％)与化合物1(91％)作为发光层50。
然后，在发光层上蒸渡10nm厚的BCP作为空穴阻挡层60。
然后，在空穴阻挡层上蒸渡30nm厚的30nm厚的AlQ3作为电子传输层70。
最后，蒸渡1nm LiF为电子注入层80和100nm Al作为器件阴极90。
器件中所述结构式
所制备的器件在20mA/cm2的工作电流密度下，亮度4362cd/m2,电流效率为21.8cd/A发射绿光CIEx为0.318,CIEy为0.618。
比较例
有机电致发光器件2的制备
方法同实施例3，但使用Ir(PPy)3(9％)和常用市售化合物CBP(91％)作为发光层，制作对比用有机发光二极管器件。
器件中所述结构式
所制备的器件在20mA/cm2的工作电流密度下，亮度为3021cd/m2,电流效率达到15.1cd/A，发射绿光CIEx为0.321,CIEy为0.613。
对比实施例3和比较例的实验结果可见，相比于广泛使用的主体材料CBP，使用本发明的有机材料制备的器件具有更好的电致发光性能，更符合高性能有机半导体器件对主体材料的要求。
Claims (8)
1.一种应用于有机发光二极管的主体材料，具有化学式(I)的结构：
其中，Ar为下列N-芳基咔唑基团中的一个：
R、R2独立选自氢，C1-C4烷基取代或未取代的C1-C4烷基，C1-C4烷基取代或者未取代的C2-C4烯烷基，C1-C4烷基取代或者未取代的C2-C4炔烷基，C6-C10的含有一个或者多个取代基R1取代或未取代的芳基，C6-C10的含有一个或者多个取代基R1取代或未取代的芳烃基，C5-C8的含有一个或者多个取代基R1取代或未取代的含有一个或者多个杂原子的杂芳基；
R1独立选自氟F，氯Cl，溴Br，碘I，氰基CN，C1-C4的烷基。
2.根据权利要求1所述的主体材料，R、R2独立选自氢，C1-C4烷基，C6-C10的含有一个或者多个取代基R1取代或未取代的芳基、芳烃基；
R1独立选自氟F，氯Cl，溴Br，碘I，C1-C4的烷基。
3.根据权利要求2所述的主体材料，R独立选自氢，甲基，叔丁基，苯基，甲苯基，萘基；
R2独立选自氢H，C1-C4烷基，C6-C10的含有一个或者多个取代基R1取代或未取代的芳基、芳烃基；
R1独立选自氟F，氯Cl，溴Br，C1-C4的烷基。
4.根据权利要求3所述的主体材料，其中R、R2独立选自氢，叔丁基，苯基，甲苯基，R1选自氢、甲基。
5.根据权利要求4所述的主体材料，其中R、R2独立选自氢，叔丁基，苯基，R1为氢。
6.根据权利要求5所述的主体材料，为下列化合物中的一个：
7.根据权利要求6所述的主体材料，为下述化合物：
8.权利要求1-7任一主体材料在有机电致发光器件，有机场效应晶体管，有机太阳能电池和有机光电传感器上的应用。
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008001621A (ja) * | 2006-06-21 | 2008-01-10 | Mitsubishi Chemicals Corp | トリチル化合物、トリチル化合物の製造方法、電荷輸送材料、発光材料及び有機電界発光素子 |
| CN104144909A (zh) * | 2011-12-28 | 2014-11-12 | 索尔维公司 | 可交联芳基胺化合物 |
| TW201542760A (zh) * | 2014-02-24 | 2015-11-16 | Universal Display Corp | 有機電致發光材料及裝置 |
| US20160071625A1 (en) * | 2013-05-22 | 2016-03-10 | Konica Minolta, Inc. | Charge-transporting thin film |
| US20160079548A1 (en) * | 2013-05-22 | 2016-03-17 | Konica Minolta, Inc. | Electronic device, organic electroluminescent element, organic thin-film solar cell, and dye-sensitized solar cell |
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| CN105566199B (zh) * | 2014-10-14 | 2018-06-26 | 北京化工大学 | 一类共轭芳炔基咔唑化合物 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008001621A (ja) * | 2006-06-21 | 2008-01-10 | Mitsubishi Chemicals Corp | トリチル化合物、トリチル化合物の製造方法、電荷輸送材料、発光材料及び有機電界発光素子 |
| CN104144909A (zh) * | 2011-12-28 | 2014-11-12 | 索尔维公司 | 可交联芳基胺化合物 |
| US20160071625A1 (en) * | 2013-05-22 | 2016-03-10 | Konica Minolta, Inc. | Charge-transporting thin film |
| US20160079548A1 (en) * | 2013-05-22 | 2016-03-17 | Konica Minolta, Inc. | Electronic device, organic electroluminescent element, organic thin-film solar cell, and dye-sensitized solar cell |
| TW201542760A (zh) * | 2014-02-24 | 2015-11-16 | Universal Display Corp | 有機電致發光材料及裝置 |
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