CN114539127B - 一种有机化合物及其应用 - Google Patents
一种有机化合物及其应用 Download PDFInfo
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- CN114539127B CN114539127B CN202210166809.6A CN202210166809A CN114539127B CN 114539127 B CN114539127 B CN 114539127B CN 202210166809 A CN202210166809 A CN 202210166809A CN 114539127 B CN114539127 B CN 114539127B
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 37
- 239000000463 material Substances 0.000 claims abstract description 50
- 150000001875 compounds Chemical class 0.000 claims description 32
- 239000010409 thin film Substances 0.000 claims description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
- -1 cyano, methyl Chemical group 0.000 claims description 9
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- 229910052805 deuterium Inorganic materials 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 150000001616 biphenylenes Chemical group 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
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- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
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- 235000010290 biphenyl Nutrition 0.000 description 1
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- 239000000969 carrier Substances 0.000 description 1
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- 238000012512 characterization method Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
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- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- 230000005283 ground state Effects 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
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- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 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
- 238000011056 performance test Methods 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
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- 229920000128 polypyrrole Polymers 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
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- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
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- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
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- 125000004306 triazinyl group Chemical group 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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- C07D403/02—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 two hetero rings
- C07D403/10—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 two hetero rings linked by a carbon chain containing aromatic rings
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- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- 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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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
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- C07D401/02—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 two hetero rings
- C07D401/10—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 two hetero rings linked by a carbon chain containing aromatic rings
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- C07D403/02—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 two hetero rings
- C07D403/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two 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
本发明提供一种有机化合物及其应用,所述有机化合物具有良好的热稳定性和成膜性,适宜的玻璃化温度Tg,利于在热真空蒸镀过程中形成稳定、均一的薄膜,同时减少相分离,保持器件的稳定性。作为有机电致发光器件发光层主体材料和/或空穴传输层材料时具有平衡的空穴和电子传输性能,同时可以获得较宽的载流子复合区域,提高器件的发光效率。
Description
技术领域
本发明属于有机电致发光材料领域,涉及一种有机化合物及其应用。
背景技术
有机电致发光材料按发光机理可分为电致荧光和电致磷光两种,荧光是单重态激子的辐射衰减跃迁,磷光则是三重态激子辐射衰减到基态所发射的光。根据自旋量子统计理论,单重态激子和三重态激子的形成概率比例是1:3。荧光材料内量子效率不超过25%的限制,外量子效率普遍低于5%;电致磷光材料的内量子效率理论上达到100%,外量子效率可达20%。
磷光重金属材料有较长的寿命,在高电流密度下,可能导致三线态-三线态湮灭和浓度淬灭,造成器件性能衰减,因此通常将重金属磷光材料掺杂到合适的主体材料中,形成一种主客体掺杂体系,使得能量传递最优化,发光效率和寿命最大化。在目前的研究现状中,重金属掺杂材料商业化已成熟,很难开发可替代的掺杂材料。因此,把重心放在研发磷光主体材料是研究者们共通的思路。
现有的磷光主体材料使得载流子在发光层中不平衡,导致效率滚降严重,这主要是由于主体材料的HOMO能级与LUMO能级与相邻层材料的能级不匹配,以及载流子运输存在明显差异。因此,在本领域,期望开发一种新的磷光主体材料,以提高器件的发光效率。
发明内容
针对现有技术的不足,本发明的目的在于提供一种有机化合物及其应用。
为达此目的,本发明采用以下技术方案:
本发明的目的之一在于提供一种有机化合物,所述所述有机化合物具有式I所示结构:
其中R1-R8各自独立选自H、取代或未取代的C1-C10的烷基、取代或未取代的C1-C10的环烷基、取代或未取代的C6-C30的芳基、取代或未取代的C3-C30的杂芳基、-OR9或-SR9;
R9选自H、取代或未取代的C1-C10的烷基、取代或未取代的C1-C10的环烷基、取代或未取代的C6-C30的芳基、取代或未取代的C3-C30的杂芳基;
L选自连接键、取代或未取代的C6-C30芳基、取代或未取代C3-C30的杂芳基;
n为0-3的整数(例如0、1、2或3),Ar选自取代或未取代的C6-C30的芳基、取代或未取代的C3-C30的杂芳基。
在本发明中,所述C1-C10各自独立地可以为C1、C2、C3、C4、C5、C6、C7、C8、C9或C10。
所述C6~C30各自独立地可以为C6、C9、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26、C28、C29等。
所述C3~C30各自独立地可以为C4、C6、C9、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26、C28、C29等。
本发明提供的有机化合物具有良好的热稳定性和成膜性,适宜的玻璃化温度Tg,利于在热真空蒸镀过程中形成稳定、均一的薄膜,同时减少相分离,保持器件的稳定性。作为有机电致发光器件发光层主体材料时具有平衡的空穴和电子传输性能,同时可以获得较宽的载流子复合区域,提高器件的发光效率。
本发明的目的之二在于提供一种有机电致发光材料,所述有机电致发光材料包括如目的之一所述的有机化合物。
本发明的目的之三在于提供一种OLED器件,所述OLED器件包括阳极、阴极以及设置于所述阳极和阴极之间的有机薄膜层,所述有机薄膜层的材料包括如目的之一所述的有机电致发光材料。
本发明的目的之四在于提供一种显示面板,所述显示面板包括如目的之三所述的OLED器件。
相对于现有技术,本发明具有以下有益效果:
本发明提供的有机化合物具有良好的热稳定性和成膜性,适宜的玻璃化温度Tg,利于在热真空蒸镀过程中形成稳定、均一的薄膜,同时减少相分离,保持器件的稳定性。作为有机电致发光器件发光层主体材料时具有平衡的空穴和电子传输性能,同时可以获得较宽的载流子复合区域,提高器件的发光效率,利用本发明的化合物作为红光主体材料或者同时作为发光层主体材料和空穴传输层材料,使得OLED器件具有较低的驱动电压、较高的发光效率和较长的使用寿命。
附图说明
图1为本发明提供的OLED器件的结构示意图,其中1为基板、2为阳极、3为空穴注入层、4为空穴传输层(包括第一空穴传输层41和第二空穴传输层42)、5为发光层、6为电子传输层、7为电子注入层、8为阴极,9为盖帽层,箭头方向表示出光方向。
具体实施方式
下面通过具体实施方式来进一步说明本发明的技术方案。本领域技术人员应该明了,所述实施例仅仅是帮助理解本发明,不应视为对本发明的具体限制。
本发明的目的之一在于提供一种有机化合物,所述所述有机化合物具有式I所示结构:
其中R1-R8各自独立选自H、取代或未取代的C1-C10的烷基、取代或未取代的C1-C10的环烷基、取代或未取代的C6-C30的芳基、取代或未取代的C3-C30的杂芳基、-OR9或-SR9;
R9选自H、取代或未取代的C1-C10的烷基、取代或未取代的C1-C10的环烷基、取代或未取代的C6-C30的芳基、取代或未取代的C3-C30的杂芳基;
L选自连接键、取代或未取代的C6-C30芳基、取代或未取代C3-C30的杂芳基;
n为0-3的整数(例如0、1、2或3),Ar选自取代或未取代的C6-C30的芳基、取代或未取代的C3-C30的杂芳基。
在本发明中,所述C1-C10各自独立地可以为C1、C2、C3、C4、C5、C6、C7、C8、C9或C10。
所述C6~C30各自独立地可以为C6、C9、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26、C28、C29等。
所述C3~C30各自独立地可以为C4、C6、C9、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26、C28、C29等。
本发明提供的有机化合物具有良好的热稳定性和成膜性,适宜的玻璃化温度Tg,利于在热真空蒸镀过程中形成稳定、均一的薄膜,同时减少相分离,保持器件的稳定性。作为有机电致发光器件发光层主体材料时具有平衡的空穴和电子传输性能,同时可以获得较宽的载流子复合区域,提高器件的发光效率。
在一个实施方式中,所述取代的C1-C10的烷基、取代的C1-C10的环烷基、取代的C1-C10的烷氧基、取代的C6-C30的芳基、取代的C6-C30的芳氧基或取代的C3-C30的杂芳基中的取代基选自氘、氟、三氟甲基、氰基、甲基、乙基、叔丁基、异丙基或甲氧基。
在一个实施方式中,所述有机化合物具有式II所示结构:
其中X1-X5各自独立地选自N或CRA,每个RA彼此独立地选自H、取代或未取代C1-C10的烷基、取代或未取代C1-C10的环烷基、取代或未取代C6-C30的芳基、取代或未取代C3-C30的杂芳基;
R1-R8以及L和n的限定与式I中相同。
在一个实施方式中,所述有机化合物具有式III所示结构:
其中X1-X3各自独立地选自N或CRA,每个RA彼此独立地选自H、取代或未取代C1-C10的烷基、取代或未取代C1-C10的环烷基、取代或未取代C6-C30的芳基、取代或未取代C3-C30的杂芳基,Ar1和Ar2独立地选自取代或未取代C6-C30的芳基、取代或未取代C3-C30的杂芳基;
R1-R8以及L和n的限定与式I中相同。
在一个实施方式中,所述有机化合物具有式IV所示结构:
其中X1-X3各自独立地选自N或CRA,每个RA彼此独立地选自H、取代或未取代C1-C10的烷基、取代或未取代C1-C10的环烷基、取代或未取代C6-C30的芳基、取代或未取代C3-C30的杂芳基,Ar1、Ar2和A独立地选自取代或未取代C6-C30的芳基、取代或未取代C3-C30的杂芳基;
R1-R8以及L和n的限定与式I中相同。
式IV中A环代表与所在环稠合。
在一个实施方式中,R1-R8各自独立选自H、氘、氟、三氟甲基、氰基、甲基、乙基、叔丁基、异丙基、环丙基、环戊基、甲氧基、苯基、氰基取代的苯基、吡啶基或苯氧基。
在一个实施方式中,L选自单键、取代或未取代的亚苯基、取代或未取代的亚联苯基或取代的或未取代的亚萘基、取代或未取代的亚苯基-亚萘基、取代或未取代的亚菲基、取代或未取代的亚吡啶基、取代或未取代的亚吡啶基-亚吡啶基。
在一个实施方式中,Ar选自取代或未取代的苯基、取代或未取代的菲基、取代或未取代的吡啶基、取代或未取代的三嗪基、取代或未取代的苯并嘧啶基、取代或未取代的芳胺基;
当为所述取代的基团时,取代基选自C6-C30(例如可以为C6、C9、C10、C12、C13、C14、C15、C16、C18、C20、C22、C24、C26、C28、C29等)的芳基。
在一个实施方式中,Ar选自
在一个实施方式中,RA选自H、苯基、联苯基或吡啶基。
在一个实施方式中,A环选自苯环或萘环。所述A环以画出,表示其与和其连接的环稠合成环结构。
在一个实施方式中,所述有机化合物为如下化合物中的任意一种:
其中D代表氘。
在一个实施方式中,所述有机化合物为如下化合物中的任意一种:
本发明的目的之二在于提供一种有机电致发光材料,所述有机电致发光材料包括如目的之一所述的有机化合物。
本发明的目的之三在于提供一种OLED器件,所述OLED器件包括阳极、阴极以及设置于所述阳极和阴极之间的有机薄膜层,所述有机薄膜层的材料包括如目的之一所述的有机电致发光材料。
在一个实施方式中,所述有机薄膜层包括发光层,所述发光层包括作为主体材料的如目的之一所述的有机化合物。
在一个实施方式中,所述有机薄膜层包括发光层和空穴传输层,所述发光层包括作为主体材料的如目的之一所述的有机化合物,所述空穴传输层的材料包括如目的之一所述的有机化合物。
本发明提供的OLED器件中,阳极材料可以为金属、金属氧化物或导电性聚合物;其中,所述金属包括铜、金、银、铁、铬、镍、锰、钯、铂等及它们的合金,所述金属氧化物包括氧化铟锡(ITO)、氧化铟锌(IZO)、氧化锌、氧化铟镓锌(IGZO)等,所述导电性聚合物包括聚苯胺、聚吡咯、聚(3-甲基噻吩)等。除以上有助于空穴注入的材料及其组合,还包括已知的适合做阳极的材料。
所述OLED器件中,阴极材料可以为金属或多层金属材料;其中,所述金属包括铝、镁、银、铟、锡、钛等及它们的合金,所述多层金属材料包括LiF/Al、LiO2/Al、BaF2/Al等。除以上有助于电子注入的材料及其组合,还包括已知的适合做阴极的材料。
所述OLED器件中,有机薄膜层包括至少一层发光层(EML)和设置于发光层两侧的空穴注入层(HIL)、空穴传输层(HTL)、电子阻挡层(EBL)、空穴阻挡层(HBL)、电子传输层(ETL)或电子注入层(EIL)中的任意一种或至少两种的组合。
所述OLED器件可以通过以下方法制备:在透明或不透明的光滑的基板上形成阳极,在阳极上形成有机薄层,在有机薄层上形成阴极。其中,形成有机薄层可采用如蒸镀、溅射、旋涂、浸渍、离子镀等已知的成膜方法。
本发明的目的之四在于提供一种显示面板,所述显示面板包括如目的之三所述的OLED器件。
本发明所述有机化合物的制备方法示例性如下所述:
Toluene代表甲苯,KO(t-Bu)代表叔丁醇甲,[Pd(cinnamyl)Cl]2代表氯化钯(1-苯基烯丙基)。
以下实施例示例性地提供了一系列具体化合物的合成方法,对于未提及具体合成方法的化合物,可以通过相似的方法进行合成,也可以采用其他现有的方法进行合成,本发明对此不做具体限定。
制备实施例1
(1)将P1-1(0.5mmol)、铁粉(0.5mmol)和PPh3(0.5mmol)加入甲苯3mL溶液中混合,放入50mL的烧瓶中,在106℃下反应10小时。冷却至室温,然后向溶液中缓慢加入饱和MgSO4水溶液和乙酸乙酯萃取三次,然后将有机层通过旋转蒸发仪去除溶剂,通过柱层析,得到粗产物P1-2。
测试目标产物P1-2的结构:通过基质辅助激光解吸电离飞行时间质谱分析得MALDI-TOF MS(m/z):C16H9N,计算值为215.1,测试值为215.0。
(2)将P1-2(0.5mmol)、P1-3(0.75mmol)、KO(t-Bu)(0.75mmol)、[Pd(cinnamyl)Cl]2(0.02mol)、Ligand(0.015mol)加入甲苯3mL溶液中混合,放入50mL的烧瓶中,在80℃下反应12小时。冷却至室温,然后向溶液中缓慢加入饱和MgSO4水溶液和乙酸乙酯萃取三次,然后将有机层通过旋转蒸发仪去除溶剂,通过柱层析,得到粗产物P1。
测试目标产物P1的结构:通过基质辅助激光解吸电离飞行时间质谱分析得MALDI-TOF MS(m/z):C37H22N4,计算值为522.2,测试值为522.1。
元素分析:理论值C,85.04;H,4.24;N,10.72;测试值C,85.04;H,4.25;N,10.72。
制备实施例2
(1)将P1-2(0.5mmol)、P5-1(0.75mmol)、KO(t-Bu)(0.75mmol)、[Pd(cinnamyl)Cl]2(0.02mol)、Ligand(0.015mol)加入甲苯3mL溶液中混合,放入50mL的烧瓶中,在80℃下反应12小时。冷却至室温,然后向溶液中缓慢加入饱和MgSO4水溶液和乙酸乙酯萃取三次,然后将有机层通过旋转蒸发仪去除溶剂,通过柱层析,得到粗产物P5。
测试目标产物P5的结构:通过基质辅助激光解吸电离飞行时间质谱分析得MALDI-TOF MS(m/z):C36H21N3,计算值为495.2,测试值为495.1。
元素分析:理论值C,87.25;H,4.27;N,8.48;测试值C,87.25;H,4.28;N,8.49。
制备实施例3
(1)将P12-1(0.5mmol)、铁粉(0.5mmol)和PPh3(0.5mmol)加入甲苯3mL溶液中混合,放入50mL的烧瓶中,在106℃下反应10小时。冷却至室温,然后向溶液中缓慢加入饱和MgSO4水溶液和乙酸乙酯萃取三次,然后将有机层通过旋转蒸发仪去除溶剂,通过柱层析,得到粗产物P12-2。
测试目标产物P12-2的结构:通过基质辅助激光解吸电离飞行时间质谱分析得MALDI-TOF MS(m/z):C16H8DN,计算值为216.1,测试值为216.0。
(2)将P12-2(0.5mmol)、P12-3(0.75mmol)、KO(t-Bu)(0.75mmol)、[Pd(cinnamyl)Cl]2(0.02mol)、Ligand(0.015mol)加入甲苯3mL溶液中混合,放入50mL的烧瓶中,在80℃下反应12小时。冷却至室温,然后向溶液中缓慢加入饱和MgSO4水溶液和乙酸乙酯萃取三次,然后将有机层通过旋转蒸发仪去除溶剂,通过柱层析,得到粗产物P12。
测试目标产物P12的结构:通过基质辅助激光解吸电离飞行时间质谱分析得MALDI-TOF MS(m/z):C37H21DN4,计算值为523.2,测试值为523.1。
元素分析:理论值C,84.87;H,4.43;N,10.70;测试值C,84.88;H,4.42;N,10.70。
制备实施例4
(1)将P1-2(0.5mmol)、P43-1(0.75mmol)、KO(t-Bu)(0.75mmol)、[Pd(cinnamyl)Cl]2(0.02mol)、Ligand(0.015mol)加入甲苯3mL溶液中混合,放入50mL的烧瓶中,在80℃下反应12小时。冷却至室温,然后向溶液中缓慢加入饱和MgSO4水溶液和乙酸乙酯萃取三次,然后将有机层通过旋转蒸发仪去除溶剂,通过柱层析,得到粗产物P43。
测试目标产物P43的结构:通过基质辅助激光解吸电离飞行时间质谱分析得MALDI-TOF MS(m/z):C34H20N2,计算值为456.2,测试值为456.1。
元素分析:理论值C,89.45;H,4.42;N,6.14;测试值C,89.45;H,4.43;N,6.14。
制备实施例5
(1)将P65-1(0.5mmol)、铁粉(0.5mmol)和PPh3(0.5mmol)加入甲苯3mL溶液中混合,放入50mL的烧瓶中,在106℃下反应10小时。冷却至室温,然后向溶液中缓慢加入饱和MgSO4水溶液和乙酸乙酯萃取三次,然后将有机层通过旋转蒸发仪去除溶剂,通过柱层析,得到粗产物P65-2。
测试目标产物P65-2的结构:通过基质辅助激光解吸电离飞行时间质谱分析得MALDI-TOF MS(m/z):C19H13N,计算值为255.1,测试值为255.0。
(2)将P65-2(0.5mmol)、P65-3(0.75mmol)、KO(t-Bu)(0.75mmol)、[Pd(cinnamyl)Cl]2(0.02mol)、Ligand(0.015mol)加入甲苯3mL溶液中混合,放入50mL的烧瓶中,在80℃下反应12小时。冷却至室温,然后向溶液中缓慢加入饱和MgSO4水溶液和乙酸乙酯萃取三次,然后将有机层通过旋转蒸发仪去除溶剂,通过柱层析,得到粗产物P65。
测试目标产物P65的结构:通过基质辅助激光解吸电离飞行时间质谱分析得MALDI-TOF MS(m/z):C30H20N2,计算值为408.2,测试值为408.1。
元素分析:理论值C,88.21;H,4.93;N,6.86;测试值C,88.21;H,4.94;N,6.86。
具体实施方式中所使用的本发明化合物的制备方法均与上述方法相似,不一一赘述,仅提供其表征结果,质谱分析与元素分析结果如表1所示。
对比例1:化合物CI
对比例2:化合物CII
表1
化合物能级的模拟计算
运用密度泛函理论(DFT),对各实施例和对比例的化合物进行能级的模拟计算。通过Gaussian 09程序包(Gaussian Inc.),在B3LYP/6-31G(d)计算水平下,优化并计算得到了分子前线轨道HOMO和LUMO的分布情况,同时基于含时密度泛函理论(TDDFT)模拟计算了化合物的最低单线态能级ES1和最低三线态能级ET1。结果如表2所示。
表2化学物能级模拟计算结果
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从表2可以看出,本发明提供的化合物P39、P41、P42、P43、P44、P47、P48、P53、P54、P58具有较浅的HUMO能级(例如<-4.91eV),有利于空穴的注入和传输。P1、P5、P10、P12、P14、P18、P19、P22、P27、P28等其他的材料具有合适的HUMO能级和LUMO能级,和较高的最低三线态能级ET1(例如>2.15eV),将该化合物适合用作红光主体材料,能提高有机发光器件的电子迁移率和发光效率。
以下列举几种本发明所述有机化合物应用于OLED器件中的应用例:
器件实施例1
本应用例提供一种OLED器件(有机发光器件),如图1所示,包括依次层叠的基板1、阳极(ITO)2、空穴注入层3、第一空穴传输层41、第二空穴传输层42、发光层5、电子传输层6、电子注入层7、阴极8(镁银电极,镁银质量比1:9)和盖帽层9(CPL)。图中箭头表示出光方向。
上述OLED器件的具体制备步骤如下:
1)将带有氧化铟锡(ITO)阳极(厚度为15nm)的玻璃基板切成50mm×50mm×0.7mm的大小,分别在异丙醇和去离子水中超声处理30分钟,然后暴露在臭氧下约10min来进行清洁,将清洗后的玻璃基板安装到真空沉积设备上;
2)在ITO阳极层上,通过真空蒸镀方式共同蒸镀空穴注入层材料(化合物b)和p掺杂材料(化合物a),掺杂比例为3%(质量比);厚度为5nm,作为空穴注入层;
3)在空穴注入层上真空蒸镀空穴传输材料(化合物c),厚度为100nm,作为第一空穴传输层;
4)在第一空穴传输层上真空蒸镀空穴传输材料(化合物d),厚度为5nm,作为第二空穴传输层;
5)在第二空穴传输层上真空共同蒸镀发光主体材料化合物P1、化合物e(蒸镀的比例1:1)和掺杂材料化合物f,掺杂比例为3%(质量比),厚度为30nm,作为发光层;
6)在发光层上真空蒸镀化合物g,厚度为30nm,作为电子传输层;
7)在电子传输层上真空共同蒸镀化合物h和n掺杂材料(化合物i),掺杂质量比例为1:1;厚度为5nm,作为电子注入层;
8)在电子注入层上真空蒸镀镁银电极,其中,Mg:Ag质量比为1:9,厚度为10nm,作为阴极;
9)在阴极上真空蒸镀化合物j,厚度为100nm,作为盖帽层。
应用例2~14,24,26~29和应用对比例1
与应用例1类似,区别仅在于,将步骤(5)中的化合物P1分别用实施例2~14,24,26~29和对比例1的化合物替换。
应用例15~23,25和应用对比例2
与应用例1类似,区别仅在于,将步骤(3)中的化合物c分别用实施例15~23,25和对比例2的化合物替换。
用Keithley 2365A数字纳伏表测试OLED器件在不同电压下的电流,然后用电流除以发光面积得到OLED器件在不同电压下的电流密度;用Konicaminolta CS-2000分光辐射亮度计测试OLED器件在不同电压下的亮度和辐射能流密度;根据OLED器件在不同电压下的电流密度和亮度,得到在相同电流密度(10mA/cm2)下的工作电压和电流效率CE(10mA/cm2)(cd/A),Von为亮度1cd/m2下的启亮电压;通过测量OLED器件的亮度达到初始亮度的95%时的时间而获得寿命LT95(在50mA/cm2测试条件下);测试数据如表3所示。
表3 OLED器件性能测试结果
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由表3可知,本发明提供的OLED器件由于采用本发明的化合物作为红光主体材料或者是空穴传输层材料,具有较低的驱动电压、较高的发光效率和较长的使用寿命。例如,启亮电压可小于等于3.89V,或小于等于3.95V;电流效率CE(10mA/cm2)可大于等于45.6cd/A,或大于等于37.6cd/A;寿命LT95可大于等于78h。相对于应用对比例1~2,本发明的OLED器件的以上性能得到明显提升,这主要得益于本发明提供的有机化合物具有合适的HOMO能级、LUMO能级、以及较高的三线态能级,能提高空穴注入能力,从而使得采用其作为红光主体材料或者是空穴传输层材料的有机发光器件获得较低的驱动电压和较高的发光效率;同时本发明提供的有机化合物还具有良好的热稳定性和成膜性,有利于器件的稳定性,提升器件寿命。
申请人声明,本发明通过上述实施例来说明本发明的有机化合物及其应用,但本发明并不局限于上述实施例,即不意味着本发明必须依赖上述实施例才能实施。所属技术领域的技术人员应该明了,对本发明的任何改进,对本发明产品各原料的等效替换及辅助成分的添加、具体方式的选择等,均落在本发明的保护范围和公开范围之内。
Claims (8)
1.一种有机化合物,其特征在于,所述有机化合物具有式I所示结构:
其中R1-R8各自独立选自H、氘、氟、三氟甲基、氰基、甲基、乙基、叔丁基、异丙基、环丙基、环戊基、甲氧基、苯基、氰基取代的苯基、吡啶基或苯氧基;
L选自单键、取代或未取代的亚苯基、取代或未取代的亚联苯基或取代的或未取代的亚萘基、取代或未取代的亚苯基-亚萘基、取代或未取代的亚菲基、取代或未取代的亚吡啶基、取代或未取代的亚吡啶基-亚吡啶基;
n为1;
Ar选自
所述取代的取代基选自氘、氟、三氟甲基、氰基、甲基、乙基、叔丁基、异丙基或甲氧基。
2.一种有机化合物,其特征在于,所述有机化合物为如下化合物中的任意一种:
其中D代表氘。
3.一种有机化合物,其特征在于,所述有机化合物为如下化合物中的任意一种:
4.一种有机电致发光材料,其特征在于,所述有机电致发光材料包括如权利要求1-3中任一项所述的有机化合物。
5.一种OLED器件,其特征在于,所述OLED器件包括阳极、阴极以及设置于所述阳极和阴极之间的有机薄膜层,所述有机薄膜层的材料包括如权利要求4所述的有机电致发光材料。
6.根据权利要求5所述的OLED器件,其特征在于,所述有机薄膜层包括发光层,所述发光层包括作为主体材料的如权利要求1-3中任一项所述的有机化合物。
7.根据权利要求5所述的OLED器件,其特征在于,所述有机薄膜层包括发光层和空穴传输层,所述发光层包括作为主体材料的如权利要求1-3中任一项所述的有机化合物,所述空穴传输层的材料包括如权利要求1-3中任一项所述的有机化合物。
8.一种显示面板,其特征在于,所述显示面板包括如权利要求5-7任一项所述的OLED器件。
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