CN105884830A - 一种双极性oled磷光主体材料以及包含该材料的发光器件 - Google Patents
一种双极性oled磷光主体材料以及包含该材料的发光器件 Download PDFInfo
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- CN105884830A CN105884830A CN201610308667.7A CN201610308667A CN105884830A CN 105884830 A CN105884830 A CN 105884830A CN 201610308667 A CN201610308667 A CN 201610308667A CN 105884830 A CN105884830 A CN 105884830A
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- 239000000463 material Substances 0.000 title claims abstract description 52
- 238000000034 method Methods 0.000 claims abstract description 18
- 230000005540 biological transmission Effects 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 4
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone powder Natural products C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 239000011521 glass Substances 0.000 claims description 7
- 238000002347 injection Methods 0.000 claims description 7
- 239000007924 injection Substances 0.000 claims description 7
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 claims description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 4
- 239000002994 raw material Substances 0.000 claims description 4
- XGRJZXREYAXTGV-UHFFFAOYSA-N chlorodiphenylphosphine Chemical compound C=1C=CC=CC=1P(Cl)C1=CC=CC=C1 XGRJZXREYAXTGV-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 claims 1
- UKOVIQFHGOCRSA-UHFFFAOYSA-N [O].C1(=CC=CC=C1)P Chemical group [O].C1(=CC=CC=C1)P UKOVIQFHGOCRSA-UHFFFAOYSA-N 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical group 0.000 abstract description 41
- 230000008901 benefit Effects 0.000 abstract description 4
- 230000009477 glass transition Effects 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000003003 spiro group Chemical group 0.000 abstract 1
- 238000001149 thermolysis Methods 0.000 abstract 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical group C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 abstract 1
- 238000005401 electroluminescence Methods 0.000 description 26
- 238000002360 preparation method Methods 0.000 description 21
- 238000012360 testing method Methods 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 11
- 150000002500 ions Chemical class 0.000 description 11
- 238000001819 mass spectrum Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000011084 recovery Methods 0.000 description 8
- 230000002194 synthesizing effect Effects 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 238000010189 synthetic method Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000007738 vacuum evaporation Methods 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 230000006798 recombination Effects 0.000 description 3
- 238000005215 recombination Methods 0.000 description 3
- -1 tri-butyl phosphine tetrafluoroborate Chemical compound 0.000 description 3
- 238000010792 warming Methods 0.000 description 3
- UZKBSZSTDQSMDR-UHFFFAOYSA-N 1-[(4-chlorophenyl)-phenylmethyl]piperazine Chemical compound C1=CC(Cl)=CC=C1C(C=1C=CC=CC=1)N1CCNCC1 UZKBSZSTDQSMDR-UHFFFAOYSA-N 0.000 description 2
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- WKGDNXBDNLZSKC-UHFFFAOYSA-N oxido(phenyl)phosphanium Chemical group O=[PH2]c1ccccc1 WKGDNXBDNLZSKC-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- LXNAVEXFUKBNMK-UHFFFAOYSA-N acetic acid;palladium Chemical compound [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 230000005525 hole transport Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/6552—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring
- C07F9/65522—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring condensed with carbocyclic rings or carbocyclic ring systems
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
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- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
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- 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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Abstract
本发明涉及一种OLED材料,其特征在于,以螺[芴‑9,9’‑氧杂蒽]和苯基膦氧结构为核心,并且结构通式为:其中Ar1和Ar2独立地选自氢以及包含杂原子的多环芳族基团,并且Ar1和Ar2不同时为氢。本发明还提供了一种制备所述OLED材料的方法。本发明还提供了一种包含所述OLED材料作为发光层的主体材料的发光器件。本发明所公开的化合物结构具有良好的传输空穴和电子的双极传输特性,具有较高的载流子传输能力,同时可有效提高分子的玻璃化转变温度和热分解温度,对进一步提高器件的寿命有极大的好处,所制备的器件能够有效的提升外量子效率、功率效率和电流效率。
Description
技术领域
本发明涉及有机电致发光领域,更特别地,涉及一种OLED材料以及包含该材料的发光器件。
背景技术
机电致发光具有超薄、自发光、视角宽、响应快、发光效率高、驱动电压低、能耗低等优点。根据激子从激发单重态或激发三重态辐射跃迁回到基态的发光过程,电致发光分为电致荧光和电致磷光两种。受到自旋统计限制,在激子的形成过程中,单重态激子和三重态激子的比例为1︰3。荧光材料因为三重态激子自旋禁阻作用,只能利用单重态激子到基态的辐射跃迁,导致电致荧光的内量子效率被限制在25%以内。电致磷光中的重金属磷光材料通过系间窜越(ISC)能同时俘获单线态和三线态的激子,内量子效率理论上达到100%,突破了传统荧光材料内量子效率不超过25%的限制。但磷光重金属材料有较长的寿命(微秒级),可能导致三线态-三线态湮灭和浓度淬灭等不良影响,从而引起器件性能衰减,因此通常将重金属磷光材料掺杂到合适的主体材料中。良好的主体材料具有以下设计要求:(i)主体材料的三线态能级应该高于磷光客体,以抑制从客体到主体的三线态能量倒流,从而将三线态激子限制在发光层内;(ii)主体材料的HOMO能级与LUMO能级应该与相邻的载流子传输层能级匹配,以减少空穴和电子注入势垒,降低器件的驱动电压,此外,主体的HOMO和LUMO能级宽度大于磷光客体材料,有利于主体到客体的能量转移以及载流子在磷光客体上的直接俘获;(iii)主体材料应具有较高的载流子传输速率以及平衡的载流子传输性能,以利于器件中空穴和电子电流的平衡以及获得较宽的载流子复合区域;(iv)主体材料应当具有良好的热稳定性和成膜性,以利于在热真空蒸镀过程中形成稳定、均一的薄膜,减少相分离,保持器件的稳定性。
传统的主体材料通常只具有单一载流子传输性质,当用空穴传输型主体或电子传输型主体时,激子的复合区域通常靠近发光层与电子传输层或空穴传输层的界面。窄的激子复合区域会导致三线态-三线态的湮灭加速,尤其在高电压下使器件效率迅速下降。分子结构中既含有电子给体单元又含有电子受体单元的双极传输主体,同时具有空穴和电子传输能力,有利于发光层中的电荷平衡。双极传输主体的引入,可拓宽激子复合区域,简化器件结构,提高器件效率。
发明内容
本发明针对上述技术问题,提供了一种双极性传输型有机电致发光主体材料,其以螺[芴-9,9’-氧杂蒽]和苯基膦氧结构为核心,并且结构通式为:
Ar1和Ar2独立地选自氢以及包含杂原子的多环芳族基团,并且Ar1和Ar2不同时为氢。
优选地,所述杂原子为N、O、S中的一种或多种。
优选地,所述包含杂原子的多环芳族基团选自:
优选地,所述材料的结构式选自:
本发明还提供了一种制备上述的OLED材料的方法,包括以下步骤:
1)在溶剂甲苯中,催化剂醋酸钯、催化剂配体三叔丁基膦四氟硼酸盐和缚酸剂碳酸钾的存在下,以3,6-二溴氧杂蒽酮或3-溴氧杂蒽酮为原料,用含杂原子的多环芳族基团取代所述3,6-二溴氧杂蒽酮的3位和6位的溴或取代所述3-溴氧杂蒽酮的3位的溴,反应式如下:
2)在溶剂四氢呋喃中,使步骤1)得到的产物与2,2’-二溴联苯反应,得到螺[芴-9,9’-氧杂蒽]结构:
3)使步骤2)得到的产物依次与正丁基锂、二苯基氯化膦反应得到所述OLED材料:
本发明还提供了一种发光器件,其包含上述OLED材料作为发光层的主体材料。
优选地,所述发光器件由ITO导电玻璃衬底101、空穴注入层102、空穴传输层103、发光层104、电子传输层105、电子注入层106和阴极层107依次堆叠而成,其中所述发光层104中包含所述OLED材料作为发光层的主体材料。
本发明的有益效果是:
本发明提供了一种双极传输型有机电致发光主体材料及其应用,并提供了该类材料的制备方法,以该材料作为主体材料制作的有机电致发光器件(例如绿色OLED器件),展示了较好的效能,其特点在于:
1.本发明所公开的化合物结构既含有具有空穴传输性能的螺[芴-9,9’-氧杂蒽]结构又包含具有电子传输性能的苯基膦氧结构,具有良好的传输空穴和电子的双极传输特性,具有较高的载流子传输能力。
2.本发明所公开的化合物结构包含螺[芴-9,9’-氧杂蒽]结构,该螺环结构具有较大的二面角,可有效降低分子间有序堆积导致的磷光淬灭,螺环结构的分子刚性特征,可有效提高分子的玻璃化转变温度和热分解温度,化合物的稳定性高,对进一步提高器件的寿命有极大的好处。
3.本发明所公开的化合物具有较高的单线态和三线态能级,进一步可作为绿光主体材料使用。应用本发明的有机化合物作为主体材料,制备的器件能够有效的提升外量子效率、功率效率和电流效率。
附图说明
图1为本发明的有机电致发光器件的示意图。
附图中,各标号所代表的部件列表如下:
101、ITO导电玻璃衬底,102、空穴注入层,103、空穴传输层,104、发光层,105、电子传输层,106、电子注入层,107、阴极层。
具体实施方式
以下结合实施例对本发明的原理和特征进行描述,所举实例只用于解释本发明,并非用于限定本发明的范围。
实施例1 化合物C02的制备
1)在氮气保护下,将原料3,6-二溴氧杂蒽酮(1.77g,5mmol)、吩噁嗪(2.02g,11mmol)和150mL甲苯加入250mL三口瓶中,然后投入催化剂醋酸钯(0.022g,0.1mmol)和催化剂配体三叔丁基膦四氟硼酸盐(0.058g,0.2mmol),缚酸剂碳酸钾(2.07g,15mmol)。体系升温至回流搅拌10小时,自然降温至20-25℃后加入50mL水淬灭反应,分液,除去溶剂,将粗品用甲苯结晶,得到2.23g中间体C02-a,收率79.9%。
高分辨质谱,ESI源,正离子模式,分子式C37H22N2O4,理论值558.1580,测试值558.1576。元素分析(C37H22N2O4),理论值C:79.56,H:3.97,N:5.02,O:11.46,实测值C:79.56,H:3.96,N:5.03,O:11.46。
2)氮气保护下,在250mL三口瓶中加入2,2’-二溴联苯(1.37g,4.4mmol)和60mL四氢呋喃,置于低温浴中降温至-78℃,滴加正丁基锂(0.31g,4.84mmol),-78℃反应2小时。将中间体C02-a(2.23g,4mmol)溶于20mL四氢呋喃并滴入上述反应体系,-78℃反应2小时。自然升温至0-5℃后加入30mL稀盐酸淬灭反应,分液,除去溶剂得到2.81g粗品,收率88.7%。将2.81g粗品加入100mL三口瓶中并加入35mL乙酸和0.5mL 36%(wt%)浓盐酸,110℃回流反应2.5小时,自然降温至20-25℃后,抽滤,收集滤饼,得到2.13g中间体C02-b,收率77.6%。
高分辨质谱,ESI源,正离子模式,分子式C49H29N2O3,理论值772.1362,测试值772.1361。元素分析(C49H29N2O3),理论值C:76.07,H:3.78,Br:10.33,N:3.62,O:6.20,实测值C:76.06,H:3.79,Br:10.33,N:3.61,O:6.21。
3)在氮气保护下,将中间体C02-b(2.13g,2.75mmol)和40mL四氢呋喃加入100mL三口瓶中,置于低温浴中降温至-78℃,滴加正丁基锂(0.194g,3.025mmol),-78℃反应2小时。将二苯基氯化膦(0.67g,3.025mmol)溶于10mL四氢呋喃并滴入上述反应体系,-78℃反应2小时。自然升温至0-5℃后加入10mL 10%(wt%)稀盐酸淬灭反应,分液,除去溶剂得到2.05g粗品,收率85%。将2.05g粗品加入100mL三口瓶中并加入35mL二氯甲烷,滴加5mL 36%(wt%)双氧水,25-30℃反应10小时,除去溶剂,甲苯结晶,得到1.53g化合物C02,收率62.2%。
高分辨质谱,ESI源,正离子模式,分子式C61H69N2O4P,理论值894.2647,测试值894.2641。元素分析(C61H69N2O4P),理论值C:81.87,H:4.39,N:3.13,O:7.15,P:3.46,实测值C:,81.86,H:4.40,N:3.13,O:7.14,P:3.47。
实施例2 化合物C03的制备
合成方法参照C02的制备方法,总收率26.5%。
高分辨质谱,ESI源,正离子模式,分子式C67H51N2O2P,理论值946.3688,测试值946.3683。元素分析(C67H51N2O2P),理论值C:84.97,H:5.43,N:2.96,O:3.38,P:3.27,实测值C:84.96,H:5.44,N:2.96,O:3.36,P:3.29。
实施例3 化合物C04的制备
合成方法参照C02的制备方法,总收率23.6%。
高分辨质谱,ESI源,正离子模式,分子式C61H39N2O2P,理论值862.2749,测试值862.2751。元素分析(C61H39N2O2P),理论值C:84.90,H:4.56,N:3.25,O:3.71,P:3.59,实测值C:84.91,H:4.57,N:3.25,O:3.71,P:3.59。
实施例4 化合物C09的制备
合成方法参照C02的制备方法,总收率21.8%。
高分辨质谱,ESI源,正离子模式,分子式C61H43N2O2P,理论值866.3062,测试值866.3061。元素分析(C61H43N2O2P),理论值C:84.51,H:5.00,N:3.23,O:3.69,P:3.57,实测值C:84.52,H:5.01,N:3.21,O:3.69,P:3.57。
实施例5 化合物C10的制备
合成方法参照C02的制备方法,总收率21.4%。
高分辨质谱,ESI源,正离子模式,分子式C65H43N2O2P,理论值914.3062,测试值914.3061。元素分析(C65H43N2O2P),理论值C:85.32,H:4.74,N:3.06,O:3.50,P:3.39,实测值C:85.31,H:4.75,N:3.07,O:3.49,P:3.39。
实施例6 化合物C11的制备
1)在氮气保护下,将原料3-溴氧杂蒽酮(1.38g,5mmol)、二苯并呋喃-4-硼酸(1.17g,5.5mmol)和150mL甲苯加入250mL三口瓶中,然后投入催化剂四(三苯基膦钯)(0.116g,0.1mmol),缚酸剂碳酸钾(1.38g,10mmol)。体系升温至回流搅拌10小时,自然降温至20-25℃后加入50mL水淬灭反应,分液,除去溶剂,将粗品用甲苯结晶,得到1.31g中间体C11-a,收率72.3%。
参照C02的制备方法完成C11的制备,总收率17.5%。
高分辨质谱,ESI源,正离子模式,分子式C49H31O3P,理论值698.2011,测试值968.1987。元素分析(C49H31O3P),理论值C:84.23,H:4.47,O:6.87,P:4.43,实测值C:84.22,H:4.48,O:6.87,P:4.43。
实施例7 化合物C22的制备
合成方法参照C02的制备方法,总收率23.2%。
高分辨质谱,ESI源,正离子模式,分子式C55H37N2O2P,理论值788.2593,测试值788.2591。元素分析(C55H37N2O2P),理论值C:83.74,H:4.73,N:3.55,O:4.06,P:3.93,实测值C:83.72,H:4.75,N:3.57,O:4.04,P:3.93。
实施例8 化合物C24的制备
合成方法参照C02的制备方法,总收率20.5%。
高分辨质谱,ESI源,正离子模式,分子式C55H34NO3P,理论值787.2276,测试值787.2271。元素分析(C55H34NO3P),理论值C:83.85,H:4.35,N:4.78,O:6.09,P:3.93,实测值C:83.86,H:4.35,N:4.77,O:6.09,P:3.93。
实施例9 化合物C28的制备
合成方法参照C02的制备方法,总收率18.3%。
高分辨质谱,ESI源,正离子模式,分子式C62H40NO2P,理论值861.2797,测试值861.2792。元素分析(C62H40NO2P),理论值C:86.39,H:4.68,N:1.62,O:3.71,P:3.59,实测值C:86.40,H:4.67,N:1.62,O:3.71,P:3.59。
有机电致发光器件实施例:
本发明选取化合物C02、化合物C03、化合物C04、化合物C09、化合物C10、化合物C11、化合物C22、化合物C24、化合物C28制作有机电致发光器件,并选择商品化的主体材料材料4,4’-二(9H-咔唑基)联苯(CBP)作为对比例,下面结合图1叙述,有机电致发光器件从下至上依次为为ITO导电玻璃衬底101、空穴注入层102、空穴传输层103、发光层104、电子传输层105、电子注入层106和阴极层107。应当理解,器件实施过程与结果,只是为了更好地解释本发明,并非对本发明的限制。
实施例10 化合物C02在有机电致发光器件中的应用
本实施例按照下述方法制备有机电致发光器件1:
1)清洗ITO(氧化铟锡)玻璃:分别用去离子水、丙酮、乙醇超声清洗ITO玻璃各30分钟,然后在等离子体清洗器中处理5分钟;
2)在阳极ITO玻璃上真空蒸镀空穴注入层m-MTDATA和F4-TCNQ,两种材料采用共蒸镀的方法,总蒸镀速率0.1nm/s,蒸镀膜厚为150nm;
3)在空穴注入层之上真空蒸镀空穴传输层NPB,蒸镀速率0.1nm/s,蒸镀膜厚为20nm;
4)在空穴传输层之上,真空蒸镀发光层实施例1制备的化合物C02:5%wt Ir(ppy)3,蒸镀速率0.1nm/s,蒸镀总膜厚为30nm;
5)在发光层之上,真空蒸镀作为电子传输层的TPBI,厚度为20nm;
6)在电子传输层之上,真空蒸镀电子注入层LiF,厚度为1nm;
7)在电子注入层之上,真空蒸镀阴极Al,厚度为100nm。
器件的结构为ITO/m-MTDATA:F4-TCNQ(150nm)/NPB(:20nm)/化合物C02:5%wt Ir(ppy)3(30nm)/TPBI(20nm)/LiF(1nm)/Al(100nm),真空蒸镀过程中,压力<4.0×10-4Pa,以化合物C02作为器件一的主体材料,所得器件的测试结果见表1所示。
对比例1:根据与实施例10相同的方法制作有机电致发光器件,区别在于使用4,4’-二(9H-咔唑基)联苯(CBP)作为发光层的主体代替作为发光层主体的实施例1中合成的C02。所得器件的测试结果见表1所示。
实施例11:化合物C03在有机电致发光器件中的应用
根据与实施例10相同的方法制作有机电致发光器件,区别在于使用C03作为发光层的主体代替作为发光层主体的实施例1中合成化合物C02。所得器件的测试结果见表1所示。
实施例12:化合物C04在有机电致发光器件中的应用
根据与实施例10相同的方法制作有机电致发光器件,区别在于使用C04作为发光层的主体代替作为发光层主体的实施例1中合成化合物C02。所得器件的测试结果见表1所示。
实施例13:化合物C09在有机电致发光器件中的应用
根据与实施例10相同的方法制作有机电致发光器件,区别在于使用C09作为发光层的主体代替作为发光层主体的实施例1中合成化合物C02。所得器件的测试结果见表1所示。
实施例14:化合物C10在有机电致发光器件中的应用
根据与实施例10相同的方法制作有机电致发光器件,区别在于使用C10作为发光层的主体代替作为发光层主体的实施例1中合成化合物C02。所得器件的测试结果见表1所示。
实施例15:化合物C11在有机电致发光器件中的应用
根据与实施例10相同的方法制作有机电致发光器件,区别在于使用C11作为发光层的主体代替作为发光层主体的实施例1中合成化合物C02。所得器件的测试结果见表1所示。
实施例16:化合物C22在有机电致发光器件中的应用
根据与实施例10相同的方法制作有机电致发光器件,区别在于使用C22作为发光层的主体代替作为发光层主体的实施例1中合成化合物C02。所得器件的测试结果见表1所示。
实施例17:化合物C24在有机电致发光器件中的应用
根据与实施例10相同的方法制作有机电致发光器件,区别在于使用C24作为发光层的主体代替作为发光层主体的实施例1中合成化合物C02。所得器件的测试结果见表1所示。
实施例18:化合物C28在有机电致发光器件中的应用
根据与实施例10相同的方法制作有机电致发光器件,区别在于使用C28作为发光层的主体代替作为发光层主体的实施例1中合成化合物C02。所得器件的测试结果见表1所示。
表1器件光电数据表
为了比较,本发明制造使用常规绿色主体材料CBP的参考器件。如表1所示,基于CBP的器件,具有4.1V的高启亮电压,最大电流效率15.6cd/A;基于本发明主体材料制备的有机电致发光器件,展示了较好的性能,器件启亮电压3.2-3.7V,最大电流效率17.6-22.6cd/A。与常规绿光主体材料CBP比较,本发明的器件在效率、驱动电压和稳定性方面表现出出色的特性。
以上所述仅为本发明的较佳实施例,并不用以限制本发明,凡在本发明的精神和原则之内,所作的任何修改、等同替换、改进等,均应包含在本发明的保护范围之内。
Claims (7)
1.一种OLED材料,其特征在于,以螺[芴-9,9’-氧杂蒽]和苯基膦氧结构为核心,并且结构通式为:
其中Ar1和Ar2独立地选自氢以及包含杂原子的多环芳族基团,并且Ar1和Ar2不同时为氢。
2.根据权利要求1所述的OLED材料,其特征在于,所述杂原子为N、O、S中的一种或多种。
3.根据权利要求1所述的OLED材料,其特征在于,所述包含杂原子的多环芳族基团的结构式选自:
4.根据权利要求1所述的OLED材料,其特征在于,所述OLED材料的结构式选自:
5.一种制备权利要求1-4中任一项所述的OLED材料的方法,其特征在于,包括以下步骤:
1)以3,6-二溴氧杂蒽酮或3-溴氧杂蒽酮为原料,用含杂原子的多环芳族基团取代所述3,6-二溴氧杂蒽酮的3位和6位的溴或取代所述3-溴氧杂蒽酮的3位的溴,反应式如下:
2)在溶剂四氢呋喃中,使步骤1)得到的产物与2,2’-二溴联苯反应,得到螺[芴-9,9’-氧杂蒽]结构:
3)使步骤2)得到的产物依次与正丁基锂、二苯基氯化膦反应得到所述OLED材料:
6.一种发光器件,包括发光层(104),其特征在于,所述发光层(104)的主体材料为权利要求1-4中任一项所述的OLED材料。
7.根据权利要求6所述的发光器件,其特征在于,所述发光器件由ITO导电玻璃衬底(101)、空穴注入层(102)、空穴传输层(103)发光层(104)、电子传输层(105)、电子注入层(106)和阴极层(107)依次堆叠而成。
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