CN113336785A - 一种含硅芴的芳香胺类化合物及其有机电致发光器件 - Google Patents
一种含硅芴的芳香胺类化合物及其有机电致发光器件 Download PDFInfo
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- CN113336785A CN113336785A CN202110710142.7A CN202110710142A CN113336785A CN 113336785 A CN113336785 A CN 113336785A CN 202110710142 A CN202110710142 A CN 202110710142A CN 113336785 A CN113336785 A CN 113336785A
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- Prior art keywords
- unsubstituted
- substituted
- aromatic amine
- layer
- silafluorene
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- -1 Aromatic amine compound Chemical class 0.000 title claims abstract description 48
- UTUZBCDXWYMYGA-UHFFFAOYSA-N silafluorene Chemical compound C12=CC=CC=C2CC2=C1C=CC=[Si]2 UTUZBCDXWYMYGA-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 230000005525 hole transport Effects 0.000 claims abstract description 26
- 239000010410 layer Substances 0.000 claims description 165
- 239000000758 substrate Substances 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
- 239000012044 organic layer Substances 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000000732 arylene group Chemical group 0.000 claims description 9
- 125000005549 heteroarylene group Chemical group 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 4
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
- BFRDBSBKJUVSNP-UHFFFAOYSA-N 9h-fluorene;silicon Chemical compound [Si].C1=CC=C2CC3=CC=CC=C3C2=C1 BFRDBSBKJUVSNP-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 51
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- 238000002425 crystallisation Methods 0.000 abstract description 3
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- 229910052757 nitrogen Inorganic materials 0.000 description 12
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
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- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
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- OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 description 4
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Chemical compound O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 4
- 238000007738 vacuum evaporation Methods 0.000 description 4
- PKMUHQIDVVOXHQ-HXUWFJFHSA-N C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O Chemical compound C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O PKMUHQIDVVOXHQ-HXUWFJFHSA-N 0.000 description 3
- SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 description 3
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- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical group C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 3
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- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 3
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- IJVBYWCDGKXHKK-UHFFFAOYSA-N 1-n,1-n,2-n,2-n-tetraphenylbenzene-1,2-diamine Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 IJVBYWCDGKXHKK-UHFFFAOYSA-N 0.000 description 2
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
- C07F7/0816—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring comprising Si as a ring atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/002—Heterocyclic compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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Abstract
本发明提供了一种含硅芴的芳香胺类化合物及其有机电致发光器件,涉及有机光电材料技术领域。本发明的含硅芴的芳香胺类化合物具有给电子能力强、空穴迁移率高、玻璃化温度高、热稳定性高和受热冷却不易结晶的特性。在OLED器件的覆盖层或空穴传输层应用于本发明化合物后,可有效提升OLED器件的光取出效率、寿命和发光效率,可以解决现有材料中折射率低,玻璃转化温度低,热稳定性差,易聚集结晶等问题。
Description
技术领域
本发明涉及有机光电材料技术领域,尤其涉及一种含硅芴的芳香胺类化合物及其有机电致发光器件。
背景技术
有机电致发光(OLED:Organic Light EmissionDiodes)器件技术既可以用来制造新型显示产品,也可以用于制作新型照明产品,有望替代现有的液晶显示和荧光灯照明,应用前景十分广泛。OLED发光器件犹如三明治的结构,包括电极材料膜层以及夹在不同电极膜层之间的有机功能材料,各种不同功能材料根据用途相互叠加在一起共同组成OLED发光器件。OLED发光器件作为电流器件,当对其两端电极施加电压,并通过电场作用有机层功能材料膜层中的正负电荷时,正负电荷进一步在发光层中复合,即产生OLED电致发光。
当前,OLED显示技术已经在智能手机,平板电脑等领域获得应用,进一步还将向电视等大尺寸应用领域扩展,但是和实际的产品应用要求相比,OLED器件的发光效率和使用寿命等性能还需要进一步提升。目前对OLED发光器件提高性能的研究包括:降低器件的驱动电压、提高器件的发光效率、提高器件的使用寿命等。为了实现OLED器件的性能的不断提升,不但需要从OLED器件结构和制作工艺的创新,更需要OLED光电功能材料不断研究和创新,创制出更高性能的OLED功能材料。
构成OLED器件的OLED光电功能材料膜层至少包括两层以上结构,产业上应用的OLED器件结构则包括空穴注入层、空穴传输层、空穴传输辅助层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层、覆盖层等多种膜层。另外,对于不同结构的OLED器件搭配而言,所使用的光电功能材料具有较强的选择性,相同的材料在不同结构器件中的性能表现也可能完全迥异。
为了制作高性能的OLED发光器件,要求各种有机功能材料具备良好的性能,譬如,作为电荷传输材料,要求具有良好的载流子迁移率、高玻璃化转化温度等,作为发光层的主体材料具有良好双极性、适当的HOMO/LUMO能阶等。
因此,针对当前OLED器件的产业应用要求以及OLED器件的不同功能膜层、器件的特性需求,必须选择更适合、性能更高的OLED功能材料或材料组合,才能实现器件的高效率、长寿命和低电压的综合特性。就当前的OLED显示照明产业的实际需求而言,目前OLED材料的发展还远远不够,落后于面板制造企业的要求,作为材料企业开发更高性能的有机功能材料显得尤为重要。
发明内容
针对现有技术存在的上述问题,本发明提供了一种含硅芴的芳香胺类化合物及其有机电致发光器件。本发明化合物应用于OLED器件的覆盖层后,可有效提升OLED器件的光取出效率,并且可作为OLED器件的空穴传输层材料,可将电子阻挡在发光层内,提高空穴和电子在发光层中的复合度,从而提升OLED器件的发光效率和使用寿命。
本发明提供了一种含硅芴的芳香胺类化合物,所述化合物选自如下式I所示:
其中,Ar1-Ar4中至少两个选自下式B,当多个式B同时存在时,多个式B彼此相同或不同;其余的相同或不同地选自取代或未取代的C6-C30的芳基、取代或未取代的C2-C30的杂芳基中的任意一种,且选自杂芳基时,不选自取代或未取代的六元含氮杂芳基;
M选自如下式中的任意一种所示:
X选自O、S、C R5R6、N-R7中的任意一种;
R1-R2、R5-R7相同或不同地选自取代或未取代的C1-C10的烷基、取代或未取代的C3-C12的环烷基、取代或未取代的C6-C12的芳基、取代或未取代的C2-C12的杂芳基中的任意一种,或R1-R2与其所连接的基团一起形成取代或未取代的螺硅芴,或R1-R2之间相互键合成五元或六元环;R3-R4相同或不同地选自H、D、-CN、取代或未取代的C1-C4的烷基、取代或未取代的C3-C10的环烷基、取代或未取代的C6-C12的芳基、取代或未取代的C2-C12的杂芳基中的任意一种,e选自0到4的整数,f选自0到6的整数,g选自0到7的整数,当e、f、g为2或更大时,多个R3、R4彼此相同或不同,相邻的多个R3之间、R4之间可以相互键合成五元或六元环;
L1-L3相同或不同地选自连接键、取代或未取代的C6-C30的亚芳基、取代或未取代的C2-C30的亚杂芳基中的任意一种;
所述烷基、环烷基、芳基、杂芳基、亚芳基、亚杂芳基的取代基分别选自D、卤素原子、-CN、C1-C4的烷基、C3-C12的环烷基、未取代的或者经C1-C4的烷基取代的C6-C12的芳基、9,9-二甲基芴基、9,9-二苯基芴基、9-苯基芴基、螺芴基、未取代的或者经C1-C4的烷基取代的C2-C12的杂芳基组成的组中的一种或一种以上,在被多个取代基取代的情况下,多个取代基彼此相同或不同。
本发明还提供了一种有机电致发光器件,所述有机电致发光器件包括覆盖层、阴极、有机物层、阳极和基板,所述覆盖层包括第一覆盖层和第二覆盖层,所述第一覆盖层或第二覆盖层至少含有一种所述含硅芴的芳香胺类化合物。
本发明还提供了一种有机电致发光器件,所述有机电致发光器件包括阴极、有机物层、阳极和基板,所述有机物层含有空穴传输层,所述空穴传输层至少含有一种所述含硅芴的芳香胺类化合物。
本发明有益效果:
本发明的含硅芴的芳香胺类化合物具有给电子能力强、空穴迁移率高、玻璃化温度高、热稳定性高和受热冷却不易结晶的特性,在OLED器件的覆盖层或空穴传输层应用于本发明化合物后,可有效提升OLED器件的光取出效率、寿命和发光效率。本发明所述化合物在OLED发光器件中具有良好的应用效果和产业化前景。
附图说明
图1为本发明的化合物1的1H NMR图;图2为本发明的化合物69的1H NMR图;
图3为本发明的化合物125的1H NMR图;图4为本发明的化合物198的1H NMR图。
具体实施方式:
下面将结合本发明实施例的技术方案进行清楚、完整地描述,显然,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域技术人员在没有做出创造性劳动前提下所获得的所有其他实施例,都属于本发明的保护范围。
在本发明中,所述烷基可以是直链或支链的,优选具有1至10个碳原子,更优选具有1至6个碳原子。所述烷基可以是取代或未取代的。具体实例包括甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、1-甲基-丁基、1-乙基-丁基、正戊基、异戊基、新戊基、叔戊基、正己基、1-甲基戊基、2-甲基戊基、4-甲基-2-戊基、2-乙基丁基、1-甲基己基、正辛基等,但不限于此。
在本发明中,所述环烷基优选具有3至12个碳原子,更优选具有3至8个碳原子。所述环烷基可以是取代或未取代的。具体实例包括环丙基、环丁基、环戊基、2,3-二甲基环戊基、环己基、4-甲基环己基、2,3-二甲基环己基、3,4,5-三甲基环己基、环庚基、降莰烷基、金刚烷基等,但不限于此。
在本发明中,所述芳基可以是单环、多环或稠环的,优选具有6至30个碳原子,更优选具有6至20个碳原子,进一步优选具有6至14个碳原子。所述芳基可以是取代或未取代的。当所述芳基是单环芳基时,具体实例包括苯基等,但不限于此;当所述芳基是多环芳基时,具体实例包括联苯基、三联苯基等,但不限于此;当所述芳基是稠环芳基时,具体实例包括萘基、蒽基、菲基、三苯基、芘基、苝基、芴基、螺芴基、茚基、荧蒽基等,但不限于此。
在本发明中,所述亚芳基意指在芳基中具有两个键合位置的基团,即二价基团。上述关于芳基的描述可以应用于亚芳基,不同之处在于亚芳基是二价的。
在本发明中,所述杂芳基包含除碳之外的一个或更多个原子,即杂原子,并且具体地杂原子可以包括选自O、N、Se和S等中的一个或更多个原子,优选具有2至20个碳原子,更优选具有2至10个碳原子,进一步优选具有2至7个碳原子。所述杂芳基可以是取代或未取代的。杂芳基可以是单环、多环或稠环的,具体实例包括噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、三唑基、吖啶基、菲啶基、哒嗪基、吡嗪基、吩嗪基、喹啉基、喹唑啉基、喹喔啉基、酞嗪基、异喹啉基、吲哚基、吲唑基、萘啶基、咔唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、苯并呋喃基、苯并噁唑基、噁唑基、噻唑基、二唑基、苯并噻唑基、吩噻嗪基、二苯并噻吩基、二苯并呋喃基、氮杂芴基、咔啉基、菲罗啉基等,但不限于此。
在本发明中,所述亚杂芳基意指在杂芳基中具有两个键合位置的基团,即二价基团。上述关于杂芳基的描述可以应用于亚杂芳基,不同之处在于亚杂芳基是二价的。
本发明所述的键合形成环是指两个基团通过化学键彼此连接并任选地芳构化。如下所示例:
本发明中,键合形成的环可以为五元环或六元环或者稠合环,例如苯基、萘基、环戊烯基、环戊烷基、环己烷并苯基、喹啉基、异喹啉基、二苯并噻吩基、菲基或芘基,但不限于此。
本发明所述的“选自0~W的整数”是指所述值选自0~W的整数中的任意一个,包括0,1,2…W-2,W-1,W。例如,“e选自0到4的整数”是指e为0,1,2,3或4;以此类推。
本发明提供了一种含硅芴的芳香胺类化合物,所述化合物选自如下式I所示:
其中,Ar1-Ar4中至少两个选自下式B,当多个式B同时存在时,多个式B彼此相同或不同;其余的相同或不同地选自取代或未取代的C6-C30的芳基、取代或未取代的C2-C30的杂芳基中的任意一种,且选自杂芳基时,不选自取代或未取代的六元含氮杂芳基;
M选自如下式中的任意一种所示:
X选自O、S、C R5R6、N-R7中的任意一种;
R1-R2、R5-R7相同或不同地选自取代或未取代的C1-C10的烷基、取代或未取代的C3-C12的环烷基、取代或未取代的C6-C12的芳基、取代或未取代的C2-C12的杂芳基中的任意一种,或R1-R2与其所连接的基础一起形成取代或未取代的螺硅芴,或R1-R2之间相互键合成五元或六元环;R3-R4相同或不同地选自H、D、-CN、取代或未取代的C1-C4的烷基、取代或未取代的C3-C10的环烷基、取代或未取代的C6-C12的芳基、取代或未取代的C2-C12的杂芳基中的任意一种,e选自0到4的整数,f选自0到6的整数,g选自0到7的整数,当e、f、g为2或更大时,多个R3、R4彼此相同或不同,相邻的多个R3之间、R4之间可以相互键合成五元或六元环;
L1-L3相同或不同地选自连接键、取代或未取代的C6-C30的亚芳基、取代或未取代的C2-C30的亚杂芳基中的任意一种;
所述烷基、环烷基、芳基、杂芳基、亚芳基、亚杂芳基的取代基分别选自D、卤素原子、-CN、C1-C4的烷基、C3-C12的环烷基、未取代的或者经C1-C4的烷基取代的C6-C12的芳基、9,9-二甲基芴基、9,9-二苯基芴基、9-苯基芴基、螺芴基、未取代的或者经C1-C4的烷基取代的C2-C12的杂芳基组成的组中的一种或一种以上,在被多个取代基取代的情况下,多个取代基彼此相同或不同。
优选的,所述化合物选自如下式中的任意一种所示:
其中,R1-R2相同或不同地选自甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、三氟甲基、环戊基、环己基、降莰烷基、金刚烷基、苯基、氘代苯基、萘基、氘代奈基、苯甲基、蒽基中的任意一种,或R1-R2与其所连接的基团一起形成取代或未取代的螺硅芴,或R1-R2之间相互键合成五元或六元饱和环;R3相同或不同地选自H、D、-CN、甲基、乙基、异丙基、叔丁基、三氟甲基、环戊基、环己基、降莰烷基、金刚烷基、苯基中的任意一种。
优选的,R1与R2一起形成-(CH2)4-或-(CH2)5-。
优选的,所述B选自如下式中任意一种所示:
优选的,所述M选自如下式中任意一种所示:
优选的,所述Ar1-Ar4中至少两个选自式B,当多个式B同时存在时,多个式B彼此相同或不同;其余的相同或不同地选自如下结构中的任意一种:
其中,R8相同或不同地选自H、D、-CN、甲基、乙基、异丙基、叔丁基、三氟甲基、环戊基、环己基、降莰烷基、金刚烷基、苯基、苯甲基、氘代苯基、二联苯基、萘基、蒽基、咔唑、芴、二苯并呋喃、二苯并噻吩中的任意一种,q选自0到5的整数,r选自0到7的整数,s选自0到9的整数,t选自0到11的整数,u选自0到4的整数,w选自0到6的整数,x选自0到8的整数,当q、r、s、t、u、w、x为2或更大时,多个R8彼此相同或不同。
更优选的,所述Ar1-Ar4中至少两个选自式B,当多个式B同时存在时,多个式B彼此相同或不同;其余的相同或不同地选自如下结构中的任意一种:
优选的,所述L1-L3选自连接键或选自如下式中任意一种所示:
最优选的,所述化合物选自如下式中任意一种所示:
本发明所述含硅芴的芳香胺类化合物的制备方法,可通过常规的偶联反应制备得到,例如可通过如下合成路线制备得到,但本发明不限于此:
1、原料1.1-1、原料1.1-2,以Pd(OAc)2、P(t-Bu)3为催化剂,叔丁醇钠为碱,得到中间体1.1-3;
2、原料1.1-4、原料1.1-5,以Pd(OAc)2、P(t-Bu)3为催化剂,叔丁醇钠为碱,得到中间体1.1-6;
3、中间体2.2-1、中间体1.1-3,以Pd(OAc)2、P(t-Bu)3为催化剂,叔丁醇钠为碱,得到中间体2.2-2;
4、中间体2.2-2、中间体1.1-6,以Pd(OAc)2、P(t-Bu)3为催化剂,叔丁醇钠为碱,得到I,所述Ar1-Ar4、M、L1-L2如上述定义,E相同或不同的选自Cl、Br、I中任意一个。
本发明对上述合成中所采用的原料的来源没有特别的限制,可以使用市售产品原料或采用本领域技术人员所熟知的制备方法得到本发明所述含硅芴的芳香胺类化合物。
本发明还提供了一种有机电致发光器件,所述有机电致发光器件包括覆盖层、阴极、有机物层、阳极和基板,所述覆盖层包括第一覆盖层和第二覆盖层,所述第一覆盖层或第二覆盖层至少含有一种所述含硅芴的芳香胺类化合物。
本发明还提供了一种有机电致发光器件,所述有机电致发光器件包括阴极、有机物层、阳极和基板,所述有机物层含有空穴传输层,所述空穴传输层至少含有一种所述含硅芴的芳香胺类化合物。
本发明的有机电致发光器件的有机功能层可以具有单层结构,或者具有两层以上的多层结构。本发明的有机电致发光器件的有机物层可以包含空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层、覆盖层或者置于阳极和空穴注入层之间的缓冲层中的任意一层或者任意多层。
优选的,本发明的阳极材料,可以选择如下材料中的一种或者多种:铜、金、银、铁、铬、镍、锰、钯、铂等及它们的合金;金属氧化物例如:氧化铟、氧化锌、氧化铟锡(简称:ITO)、氧化铟锌(简称:IZO)、氧化铝锌、ITO-Ag-ITO等;导电性聚合物例如:聚苯胺、聚吡咯、聚(3-甲基噻吩)等,但不限于此。除了以上材料及其组合之外,阳极材料还可包括其他已知的适合做阳极的材料。
优选的,本发明的空穴注入材料具有较好的空穴注入性能,可以选择如下材料中的一种或者多种:三氧化钼、氧化银、三氧化钨、氧化钌、氧化镍、氧化铜、二氧化钛、三氧化二铝、酞菁铜(II)(简称:CuPc)、氧钛酞菁(简称:TiOPC)、2,3,6,7,10,11-六氰基-1,4,5,8,9,12-六氮杂苯并菲(简称HAT-CN)、4,4',4”-三(2-萘基苯基氨基)三苯基胺(简称:2T-NATA)等,但不限于此。其可以是单一物质构成的单一结构,也可是不同物质形成的单层结构或多层结构。
优选的,本发明的空穴传输材料具有较好的空穴传输性能,可以选自如下材料中的一种或者多种:本发明的含硅芴的芳香胺类化合物、4,4',4”-三(N,N-二苯基氨基)三苯胺(简称:TDATA)、N,N'-二(萘-1-基)-N,N'-二(苯基)-2,2'-二甲基联苯胺(简称:α-NPD)、N,N'-二苯基-N,N'-(1-萘基)-1,1'-联苯-4,4'-二胺(简称:NPB)等,但不限于此。其可以是单一物质构成的单一结构,也可是不同物质形成的单层结构或多层结构。更优选的,所述空穴传输材料选自本发明含硅芴的芳香胺类化合物。
优选的,本发明所述电子阻挡层材料,可以选自如下材料中的一种或者多种:4,4',4”-三(N,N-二苯基氨基)三苯胺(简称:TDATA)、N,N'-二苯基-N,N'-二(3-甲基苯基)-1,1'-联苯-4,4'-二胺(简称:TPD)、4,4'-环己基二[N,N-二(4-甲基苯基)苯胺](简称:TAPC)、2,2,7,7-四(二苯基氨基)-9,9-螺二芴(简称:Spiro-TAD)等,但不限于此。其可以是单一物质构成的单一结构,也可是不同物质形成的单层结构或多层结构。
优选的,本发明的发光层,可以是主客体的形式、可以是包含一种材料或可以包含两种以上的混合材料,本发明所述主体材料可以选自如下材料:4,4'-二(9-咔唑)联苯(简称:CBP)、9,10-二(2-萘基)蒽(简称:ADN)、9,9'-(1,3-苯基)二-9H-咔唑(简称:mCP)、4,4',4”-三(咔唑-9-基)三苯胺(简称:TCTA)、9,10-二(1-萘基)蒽(简称:α-AND)、1,3,5-三(9-咔唑基)苯(简称:TCP)等,但不限于此。发光层主体材料还可包括其他已知的适合做发光层的材料,其可以是单一物质构成的单一结构,也可是不同物质形成的单层结构或多层结构。
优选的,本发明的发光层客体材料可以选自如下材料:4,4'-二[4-(二苯氨基)苯乙烯基]联苯(简称:BDAVBi)、4,4'-二[4-(二对甲苯基氨基)苯乙烯基]联苯(简称:DPAVBi)、4,4'-双(9-乙基-3-咔唑乙烯基)-1,1'-联苯(简称:BCzVBi)、二(4,6-二氟苯基吡啶-C2,N)吡啶甲酰合铱(简称:FIrpic)、三(2-苯基吡啶)合铱(简称:Ir(ppy)3)、乙酰丙酮酸二(2-苯基吡啶)铱(简称:Ir(ppy)2(acac))、三[1-苯基异喹啉-C2,N]铱(III)(简称:Ir(piq)3)、二(1-苯基异喹啉)(乙酰丙酮)合铱(简称:Ir(piq)2(acac))等,但不限于此。发光层客体材料还可包括其他已知的适合做发光层的材料。
优选的,本发明所述的空穴阻挡层材料,可以选自如下材料中的一种或者多种:2,9-二甲基-4,7-联苯-1,10-菲罗啉(简称:BCP)、1,3,5-三(N-苯基-2-苯并咪唑)苯(简称:TPBi)、三(8-羟基喹啉)铝(简称:Alq3)、8-羟基喹啉锂(简称:Liq)、双(2-甲基-8-羟基喹啉-N1,O8)-(1,1'-联苯-4-羟基)铝(简称:BAlq)等,但不限于此。其可以是单一物质构成的单一结构,也可是不同物质形成的单层结构或多层结构。
优选的,本发明所述的电子传输层材料,可以选自如下材料中的一种或者多种:噁二唑衍生物、2,9-二甲基-4,7-联苯-1,10-菲罗啉(简称:BCP)、1,3,5-三(N-苯基-2-苯并咪唑)苯(简称:TPBi)、三(8-羟基喹啉)铝(简称:Alq3)、8-羟基喹啉锂(简称:Liq)、4,7-二苯基-1,10-菲罗啉(简称:Bphen)、3-(联苯-4-基)-5-(4-叔丁基苯基)-4-苯基-4H-1,2,4-三唑(简称:TAZ)、双(2-甲基-8-羟基喹啉-N1,O8)-(1,1'-联苯-4-羟基)铝(简称:BAlq)等,但不限于此。其可以是单一物质构成的单一结构,也可是不同物质形成的单层结构或多层结构。
优选的,本发明的电子注入材料,可以选自如下材料中的一种或者多种:Li、Na、K、Rb、Cs、Be、Mg、Ca、Sr、Ba、氟化锂、氟化钠、氟化钾、氟化铷、氟化铯、氟化镁、氟化钙、8-羟基喹啉锂等,但不限于此。其可以是单一物质构成的单一结构,也可是不同物质形成的单层结构或多层结构。
优选的,本发明所述的阴极材料,可以选自如下材料中的一种或者多种:铜、金、银、铁、铬、镍、锰、钯、铂等及它们的合金;多层金属材料例如:LiF/Al、Mg/Ag、Li/Al、LiO2/Al、BaF2/Al等,但不限于此。除以上材料及其组合之外,阴极材料还可包括其他已知的适合做阴极的材料。
优选的,本发明所述的覆盖层材料,所述覆盖层包含第一覆盖层和第二覆盖层,第一覆盖层和第二覆盖层的蒸镀顺序没有特别限定。可以选自如下材料中的一种或者多种:本发明的含硅芴的芳香胺类化合物、N,N'-[二(1-萘基)-N,N'-二苯基]-1,1'-联苯基)-4,4'-二胺(简称:NPB),或,2,9-二甲基-4,7-二苯基-1,10-菲啰啉(简称:BCP)、4,4',4”-三(N-3-甲基苯基-N-苯基氨基)三苯胺(简称:m-MTDATA)、LaB6、ZTO、Al2O3、MgO、TiO2、MgF2、12CaO·7Al2O3、SiO2、SiNx、SnO2、ZnO、ZrO2、WO3、MoO3、TPD、Alq3、CBP、TPBi等,但不限于此。更优选的,所述覆盖层选自本发明含硅芴的芳香胺类化合物。
本发明的有机电致发光器件的器件结构优选为:
基板/阳极/空穴传输层/发光层/电子传输层/阴极;
基板/阳极/空穴传输层/发光层/电子传输层/电子注入层/阴极;
基板/阳极/空穴注入层/空穴传输层/发光层/电子传输层/阴极;
基板/阳极/空穴注入层/空穴传输层/发光层/电子传输层/电子注入层/阴极;
基板/阳极/空穴注入层/空穴传输层/电子阻挡层/发光层/电子传输层/电子注入层/阴极;
基板/阳极/空穴注入层/空穴传输层/发光层/空穴阻挡层/电子传输层/电子注入层/阴极;
基板/阳极/空穴注入层/空穴传输层/电子阻挡层/发光层/空穴阻挡层/电子传输层/电子注入层/阴极;
基板/阳极/空穴传输层/发光层/电子传输层/阴极/覆盖层;
基板/阳极/空穴传输层/发光层/电子传输层/电子注入层/阴极/覆盖层;
基板/阳极/空穴注入层/空穴传输层/发光层/电子传输层/阴极/覆盖层;
基板/阳极/空穴注入层/空穴传输层/发光层/电子传输层/电子注入层/阴极/覆盖层;
基板/阳极/空穴注入层/空穴传输层/发光层/空穴阻挡层/电子传输层/电子注入层/阴极/覆盖层;
基板/阳极/空穴注入层/空穴传输层/电子阻挡层/发光层/电子传输层/电子注入层/阴极/覆盖层;
基板/阳极/空穴注入层/空穴传输层/电子阻挡层/发光层/空穴阻挡层/电子传输层/电子注入层/阴极/覆盖层等,但有机电致发光器件的结构不限于此。
本发明对有机电致发光器件的各有机物层的厚度并没有特殊限制,采用本领域所常用的厚度即可。
本发明有机电致发光器件可以采用喷墨打印、旋转涂布、丝网印刷等溶液涂布或真空蒸镀等多种方法制备得到。
本发明对以下实施例中所采用的原料的来源没有特别的限制,可以为市售产品或采用本领域技术人员所熟知的制备方法制备得到。中间体的制备可重复多次以积累足够的量。
本发明所述有机发电致光器件可广泛应用于面板显示、照明、OLED、太阳能电池、有机感光体或有机薄膜晶体管、指示牌、信号灯等领域。
实施例
将通过合成实施例和器件实施例来更加具体的描述本发明,但是本发明的范围并不限于下列合成实施例和器件实施例。
化合物的制备及表征
原料、试剂以及表征设备的说明:
质谱使用英国沃特斯G2-Si四极杆串联飞行时间高分辨质谱仪,氯仿为溶剂;
元素分析使用德国Elementar公司的Vario EL cube型有机元素分析仪,样品质量为5~10mg;
核磁共振(1HNMR)使用Bruker-510型核磁共振谱仪(德国Bruker公司),600MHz,CDCl3为溶剂,TMS为内标。
合成实施例1:化合物1的合成:
在250ml的三口瓶中,通氮气保护下,加入1-1(1.86g,0.020mol)、2-1(3.46g,0.012mol),用150ml甲苯搅溶解,然后加入5×10-5mol Pd(OAc)2、5×10-5mol P(t-Bu)3、0.03mol叔丁醇钠,加热至105℃,搅拌回流反应8小时后,降至室温后分液,水相用甲苯萃取,合并有机相,无水硫酸钠干燥,减压旋干溶剂,柱层析分离提纯(洗脱剂为石油醚:DCM=10:1~1:1),并重结晶得到中间体3-1(3.07g,HPLC纯度99.8%);
在250ml的三口瓶中,通氮气保护下,加入中间体3-1(4.22g,0.014mol)、4-1(1.86g,0.006mol)、5×10-5mol Pd(OAc)2、5×10-5mol P(t-Bu)3、0.03mol叔丁醇钠,加毕加热至115℃,搅拌回流反应20小时,TLC监控反应终点。降至室温后分液,水相用甲苯萃取,合并有机相,无水硫酸钠干燥,减压旋干溶剂,柱层析分离提纯(洗脱剂为石油醚:DCM=10:1~1:1),得到化合物1(3.61g,HPLC纯度99.5%)。质谱m/z:753.1074(理论值:753.1080)。理论元素含量(%)C52H44N2Si2:C,82.90;H,5.88;N,3.76。实测元素含量(%)C,82.94;H,5.86;N,3.74。1H NMR(600MHz,CDCl3)δ7.86(dd,2H),7.73(dd,2H),7.67(dd,2H),7.54(t,2H),7.51(s,1H),7.51(s,1H),7.46–7.44(m,8H),7.31(dd,4H),7.24(t,4H),7.08(dd,4H),7.00(m,2H),0.66(s,12H),上述结果证实获得产物为目标产品。
合成实施例2:化合物20的合成
化合物20的制备方法同实施例1,不同之处在于将2-1替换为等摩尔的2-2、将4-1替换为等摩尔的4-2。得到目标化合物20(3.23g;HPLC纯度99.4%)。质谱m/z:793.1721(理论值:793.1730)。理论元素含量(%)C55H48N2Si2:C,83.29;H,6.10;N,3.53。实测元素含量(%)C,83.25;H,6.13;N,3.54。上述结果证实获得产物为目标产品。
合成实施例3:化合物49的合成
化合物49的制备方法同实施例1,不同之处在于将1-1替换为等摩尔的1-2、将4-1替换为等摩尔的4-3。得到目标化合物49(4.37g;HPLC纯度99.2%)。质谱m/z:829.2054(理论值:829.2060)。理论元素含量(%)C58H48N2Si2:C,84.01;H,5.83;N,3.38。实测元素含量(%)C,84.04;H,5.78;N,3.40。上述结果证实获得产物为目标产品。
合成实施例4:化合物69的合成
化合物69的制备方法同实施例1,不同之处在于将4-1替换为等摩尔的4-4。得到目标化合物69(3.49g;HPLC纯度99.6%)。质谱m/z:767.0902(理论值:767.0910)。理论元素含量(%)C52H42N2OSi2:C,81.42;H,5.52;N,3.65。实测元素含量(%)C,81.37;H,5.55;N,3.67。1H NMR(600MHz,CDCl3)δ7.86(dd,2H),7.75(d,4H),7.69(dd,2H),7.54(m,2H),7.51(s,2H),7.50(dd,1H),7.48(dd,1H),7.47–7.44(m,2H),7.41(s,2H),7.24(t,4H),7.15(m,2H),7.08(dd,4H),7.02–6.99(m,2H),0.66(s,12H),上述结果证实获得产物为目标产品。
合成实施例5:化合物72的合成
化合物72的制备方法同实施例1,不同之处在于将4-1替换为等摩尔的4-5。得到目标化合物72(3.57g;HPLC纯度99.7%)。质谱m/z:783.1511(理论值:783.1520)。理论元素含量(%)C52H42N2SSi2:C,79.75;H,5.41;N,3.58。实测元素含量(%)C,79.78;H,5.42;N,3.62。上述结果证实获得产物为目标产品。
合成实施例6:化合物125的合成
化合物125的制备方法同实施例1,不同之处在于将4-1替换为等摩尔的4-3。得到目标化合物125(3.33g;HPLC纯度99.5%)。质谱m/z:677.0091(理论值:677.0100)。理论元素含量(%)C46H40N2Si2:C,81.61;H,5.96;N,4.14。实测元素含量(%)C,81.65;H,5.94;N,4.12。1H NMR(600MHz,CDCl3)δ7.86(dd,2H),7.74(dd,1H),7.73(dd,1H),7.69(d,1H),7.67(d,1H),7.54(m,2H),7.51(s,2H),7.45(m,4H),7.24(t,4H),7.08(dd,4H),7.05(d,4H),7.02–6.99(m,2H),0.66(s,12H),上述结果证实获得产物为目标产品。
合成实施例7:化合物141的合成
化合物141的制备方法同实施例1,不同之处在于将1-1替换为等摩尔的1-3、将4-1替换为等摩尔的4-6。得到目标化合物141(3.35g;HPLC纯度99.3%)。质谱m/z:777.1293(理论值:777.1300)。理论元素含量(%)C54H44N2Si2:C,83.46;H,5.71;N,3.60。实测元素含量(%)C,83.41;H,5.74;N,3.62。上述结果证实获得产物为目标产品。
合成实施例8:化合物170的合成
化合物170的制备方法同实施例1,不同之处在于将1-1替换为等摩尔的1-4、将4-1替换为等摩尔的4-3。得到目标化合物170(4.12g;HPLC纯度99.4%)。质谱m/z:941.4832(理论值:941.4840)。理论元素含量(%)C62H56N2Si4:C,79.10;H,6.00;N,2.98。实测元素含量(%)C,79.05;H,6.02;N,3.01。上述结果证实获得产物为目标产品。
合成实施例9:化合物176的合
化合物176的制备方法同实施例1,不同之处在于将2-1替换为等摩尔的2-3、将4-1替换为等摩尔的4-7。得到目标化合物176(3.48g;HPLC纯度99.2%)。质谱m/z:829.2051(理论值:829.2060)。理论元素含量(%)C58H48N2Si2:C,84.01;H,5.83;N,3.38。实测元素含量(%)C,84.06;H,5.80;N,3.36。上述结果证实获得产物为目标产品。
合成实施例10:化合物184的合成
化合物184的制备方法同实施例1,不同之处在于将1-1替换为等摩尔的1-4、将4-1替换为等摩尔的4-8。得到目标化合物184(2.75g;HPLC纯度99.1%)。质谱m/z:677.0093(理论值:677.0100)。理论元素含量(%)C46H40N2Si2:C,81.61;H,5.96;N,4.14。实测元素含量(%)C,81.55;H,5.99;N,4.17。上述结果证实获得产物为目标产品。
合成实施例11:化合物198的合成
化合物197的制备方法同实施例1,不同之处在于将2-1替换为等摩尔的2-4、将4-1替换为等摩尔的4-9。得到目标化合物197(3.36g;HPLC纯度99.3%)。质谱m/z:727.0695(理论值:727.0700)。理论元素含量(%)C50H42N2Si2:C,82.60;H,5.82;N,3.85。实测元素含量(%)C,82.63;H,5.83;N,3.81。1H NMR(600MHz,CDCl3)δ8.33(dd,2H),7.86(dd,2H),7.79(dd,2H),7.61–7.59(d,1H),7.59–7.57(dd,1H),7.55(m,2H),7.50(d,2H),7.48–7.44(m,5H),7.39(dd,1H),7.31(d,2H),7.24(t,4H),7.17(dd,2H),7.14(dd,2H),7.00(m,2H),0.66(s,12H),上述结果证实获得产物为目标产品。
合成实施例12:化合物204的合成
化合物204的制备方法同实施例1,不同之处在于将4-1替换为等摩尔的4-9。得到目标化合物204(3.29g;HPLC纯度99.5%)。质谱m/z:753.1073(理论值:753.1080)。理论元素含量(%)C52H44N2Si2:C,82.93;H,5.89;N,3.72。实测元素含量(%)C,82.95;H,5.5.83;N,3.76。
Tg温度由美国TA公司的型号:25型差示扫描量热仪测定,测试气氛为氮气,氮气的流量为50ml/min;升温速率10%/min;扫描范围为50~350℃;化合物样品的质量为1~6mg;
折射率(n)由美国J.A.Woollam公司的型号:M-2000光谱型椭偏仪测量,测试为大气环境,仪器扫描范围为245nm~1000nm;玻璃基板大小为200×200mm,材料薄膜厚度为20~60nm。
对合成实施例制备的化合物1、20、49、69、72、125、141、170、176、184、198、204和对比化合物CP1分别进行玻璃转化温度及折射率的测试,测试结果如表1
所示:
表1
器件性能
有机材料以及设备的说明:
本发明所用的有机材料都是经过升华,纯度在99.99%以上;
驱动电压、发光效率的测试是通过测试软件、计算机、美国Keithley公司生产的K2400数字源表和美国Photo Research公司的PR788光谱扫描亮度计组成一个联合IVL测试系统来测试;
寿命的测试采用McScience公司的M6000OLED寿命测试系统,测试环境为大气环境,温度为室温。
以下通过器件实施例1-19和比较例1-4详细说明本发明合成的OLED材料在器件中的应用效果。
器件实施例1
将ITO-Ag-ITO玻璃基板进行洗涤,即依次进行碱洗涤、纯水洗涤、干燥,再进行紫外线-臭氧洗涤以清除基板表面的有机残留物。进行了上述洗涤之后,在ITO-Ag-ITO透明电极上,利用真空蒸镀装置,蒸镀10nm厚度的HAT-CN作为空穴注入层。接着蒸镀60nm厚度的NPB作为空穴传输层。再蒸镀30nm厚度的CBP和BCzVBi(重量比为90:10)作为发光层。继续真空蒸镀40nm厚度的ET-1和Liq作为空穴阻挡/电子传输层。在空穴阻挡/电子传输层上,通过真空蒸镀装置,蒸镀1nm厚度的氟化锂(LiF)作为电子注入层。再蒸镀15nm厚度的Mg:Ag作为阴极层。真空蒸镀第一覆盖层50nm厚度的化合物1和第二覆盖层50nm厚度的CP1共同作为覆盖层。如上所述地完成OLED发光器件后,用公知的驱动电路将阳极和阴极连接起来,测量器件的电流效率以及器件的寿命。
表2
表3
表4
由表4的结果可以看出,实施例1-19与比较例1-4进行比较,比较例中化合物与本发明化合物相比,在有机发光器件中,本发明化合物的效率和寿命方面明显优于比较例中化合物,本发明的含硅芴的芳香胺类化合物是性能良好的有机电致发光材料。
本申请虽然以较佳实施例公开如上,任何本领域技术人员在不脱离本申请构思的前提下,都可以做出若干可能的变动和修改,因此本申请的保护范围应当以本申请权利要求所界定的范围为准。
Claims (10)
1.一种含硅芴的芳香胺类化合物,其特征在于,所述化合物选自如下式Ⅰ所示:
其中,Ar1-Ar4中至少两个选自下式B,当多个式B同时存在时,多个式B彼此相同或不同;其余的相同或不同地选自取代或未取代的C6-C30的芳基、取代或未取代的C2-C30的杂芳基中的任意一种,且选自杂芳基时,不选自取代或未取代的六元含氮杂芳基;
M选自如下式中的任意一种所示:
X选自O、S、CR5R6、N-R7中的任意一种;
R1-R2、R5-R7相同或不同地选自取代或未取代的C1-C10的烷基、取代或未取代的C3-C12的环烷基、取代或未取代的C6-C12的芳基、取代或未取代的C2-C12的杂芳基中的任意一种,或R1-R2与其所连接的基团一起形成取代或未取代的螺硅芴,或R1-R2之间相互键合成五元或六元环;R3-R4相同或不同地选自H、D、-CN、取代或未取代的C1-C4的烷基、取代或未取代的C3-C10的环烷基、取代或未取代的C6-C12的芳基、取代或未取代的C2-C12的杂芳基中的任意一种,e选自0到4的整数,f选自0到6的整数,g选自0到7的整数,当e、f、g为2或更大时,多个R3、R4彼此相同或不同,相邻的多个R3之间、R4之间可以相互键合成五元或六元环;
L1-L3相同或不同地选自连接键、取代或未取代的C6-C30的亚芳基、取代或未取代的C2-C30的亚杂芳基中的任意一种;
所述烷基、环烷基、芳基、杂芳基、亚芳基、亚杂芳基的取代基分别选自D、卤素原子、-CN、C1-C4的烷基、C3-C12的环烷基、未取代的或者经C1-C4的烷基取代的C6-C12的芳基、9,9-二甲基芴基、9,9-二苯基芴基、9-苯基芴基、螺芴基、未取代的或者经C1-C4的烷基取代的C2-C12的杂芳基组成的组中的一种或一种以上,在被多个取代基取代的情况下,多个取代基彼此相同或不同。
5.根据权利要求1中所述一种含硅芴的芳香胺类化合物,其特征在于,所述Ar1-Ar4中至少两个选自式B,当多个式B同时存在时,多个式B彼此相同或不同;其余的相同或不同地选自如下结构中的任意一种:
其中,R8相同或不同地选自H、D、-CN、甲基、乙基、异丙基、叔丁基、三氟甲基、环戊基、环己基、降莰烷基、金刚烷基、苯基、苯甲基、氘代苯基、二联苯基、萘基、蒽基、咔唑、芴、二苯并呋喃、二苯并噻吩中的任意一种,q选自0到5的整数,r选自0到7的整数,s选自0到9的整数,t选自0到11的整数,u选自0到4的整数,w选自0到6的整数,x选自0到8的整数,当q、r、s、t、u、w、x为2或更大时,多个R8彼此相同或不同。
9.一种有机电致发光器件,所述有机电致发光器件包括覆盖层、阴极、有机物层、阳极和基板,其特征在于,所述覆盖层包括第一覆盖层和第二覆盖层,所述第一覆盖层或第二覆盖层至少含有一种权利要求1-8任一项所述的含硅芴的芳香胺类化合物。
10.一种有机电致发光器件,所述有机电致发光器件包括阴极、有机物层、阳极和基板,其特征在于,所述有机物层含有空穴传输层,所述空穴传输层至少含有一种权利要求1-8中任意一项所述的含硅芴的芳香胺类化合物。
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