CN110951485B - 一种有机电致发光化合物及其制备方法和应用 - Google Patents
一种有机电致发光化合物及其制备方法和应用 Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 96
- 238000002360 preparation method Methods 0.000 title abstract description 9
- -1 boric acid compound Chemical class 0.000 claims description 41
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 21
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- 239000000203 mixture Substances 0.000 claims description 10
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 7
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- 229910002027 silica gel Inorganic materials 0.000 claims description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 229910052796 boron Inorganic materials 0.000 claims description 6
- 239000011259 mixed solution Substances 0.000 claims description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 6
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- 101150075118 sub1 gene Proteins 0.000 claims description 3
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 claims description 3
- BMIBJCFFZPYJHF-UHFFFAOYSA-N 2-methoxy-5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound COC1=NC=C(C)C=C1B1OC(C)(C)C(C)(C)O1 BMIBJCFFZPYJHF-UHFFFAOYSA-N 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 abstract description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 abstract description 6
- 125000003118 aryl group Chemical group 0.000 abstract description 5
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- 125000003282 alkyl amino group Chemical group 0.000 abstract description 3
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
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- 235000019341 magnesium sulphate Nutrition 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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- 125000000217 alkyl group Chemical group 0.000 description 5
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
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- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 3
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- 101100450129 Caenorhabditis elegans hal-3 gene Proteins 0.000 description 3
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
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- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
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- 125000001624 naphthyl group Chemical group 0.000 description 2
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- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 2
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- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 2
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- 238000007740 vapor deposition Methods 0.000 description 2
- 125000006743 (C1-C60) alkyl group Chemical group 0.000 description 1
- 125000006744 (C2-C60) alkenyl group Chemical group 0.000 description 1
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- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
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- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 1
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- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
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- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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- 238000006731 degradation reaction Methods 0.000 description 1
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- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 239000011737 fluorine Substances 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
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- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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Abstract
本发明公开了一种有机电致发光化合物及其制备方法和应用,所述有机电致发光化合物的分子结构通式由式1表示:其中,所述式1中,Ar1‑Ar4各自独立地选自取代或非取代的C1‑C30烷基、取代或非取代的C3‑C30环烷基、取代或非取代的C3‑C30杂环烷基、取代或非取代的C1‑C8烷氧基、取代或非取代的C2‑C6烯基、取代或非取代的C2‑C6炔基、C1‑C30烷基氨基、C6‑C30芳基氨基、取代或非取代的C6‑C30芳基、C6‑C30芳氧基、取代或非取代的C4‑C12杂芳基;L1‑L5各自独立地选自连接键、C6‑C60芳基、芴基、C3‑C60脂肪族环,C2‑C60杂环基。本发明所得含有有机电致发光化合物的有机电致发光器件具有高发光效率,低驱动电压和高耐热性,能显著改善色纯度和寿命。
Description
技术领域
本发明属于发光材料技术领域,更具体的说是涉及一种有机电致发光化合物及其制备方法和应用。
背景技术
有机电致发光现象是指电能转换成有机材料的光能的现象。有机EL元件是利用了如下原理的自发光元件:通过施加电场,利用由阳极注入的空穴与由阴极注入的电子的复合能使荧光性物质发光。它具有如下结构:阳极、阴极以及介于两者之间的有机层。为了提高有机EL元件的效率和稳定性,有机材料层包括具有不同材料的多层,例如空穴注入层(HIL)、空穴传输层(HTL)、发光层、电子传输层(ETL)和电子注入层(EIL)。用作有机电元件中的有机材料层的材料根据其功能可以分为发光材料和电荷传输材料,例如,空穴注入材料,空穴传输材料,电子传输材料,电子注入材料等。
随着便携式显示器市场中显示器尺寸变得越来越大,功耗也需要更多,而功耗是具有有限电池电源的便携式显示器中非常重要的因素,此外还有效率和寿命的问题。效率,寿命,驱动电压等彼此相关,仅通过简单地改善有机材料层并不能得到最大化效率。此外,为了解决最近的有机电子元件中的空穴传输层的发光问题,在空穴传输层和发光层之间存在发光辅助层。
从电子传输层转移到发光层的电子和从空穴传输层转移到发光层的空穴重新结合以形成激子。然而,由于空穴传输层中使用的材料应具有低HOMO值,因此其主要具有低T1值。由此,从发光层产生的激子被传输到空穴传输层,导致发光层中的电荷不平衡。发光在空穴传输层中或在空穴传输层的界面处发生,使得有机电致发光器件的色纯度,效率和寿命降低。并且,当使用具有快速空穴迁移率的材料来降低驱动电压时,倾向于降低效率。在OLED中,由于空穴迁移率比电子迁移率快,导致发光层中的电荷不平衡,并且发生了降低效率和寿命。
由此可知,发光辅助层必须由能够解决空穴传输层问题的材料形成,具有合适的空穴迁移率以提供合适的驱动电压,高T1能量值和宽带隙。但仅仅通过关于发光辅助层材料的核心结构特征不满足这些要求。
因此,结合上述问题,提供一种具有高T1能量值和宽带隙,能提高有机电子元件的效率和寿命的发光辅助层的材料,是本领域技术人员亟需解决的问题。
发明内容
有鉴于此,本发明提供了一种有机电致发光化合物及其制备方法和应用,本发明对制备的有机电致发光化合物应用,所得的有机电致发光器件不仅具有高发光效率,低驱动电压和高耐热性,而且能显著改善色纯度和寿命。
为了实现上述目的,本发明采用如下技术方案:
一种有机电致发光化合物,其分子结构通式由式1表示:
其中,所述式1中,Ar1-Ar4各自独立地选自取代或非取代的C1-C30烷基、取代或非取代的C3-C30环烷基、取代或非取代的C3-C30杂环烷基、取代或非取代的C1-C8烷氧基、取代或非取代的C2-C6烯基、取代或非取代的C2-C6炔基、C1-C30烷基氨基、C6-C30芳基氨基、取代或非取代的C6-C30芳基、C6-C30芳氧基、取代或非取代的C4-C12杂芳基;
L1-L5各自独立地选自连接键、C6-C60芳基、芴基、C3-C60脂肪族环、C2-C60杂环基。
优选的,所述Ar1-Ar4各自独立地选自C6-C12芳基,并且更优选为苯基、联苯、萘基、芴基、螺二芴基、二苯并呋喃、二苯并噻吩。
优选的,所述L1-L5各自独立地选自C6-C13芳基、芴基、C3-C12杂环基。
优选的,所述L1-L5各自独立地选自苯基、氘代苯基、甲基芴基、吡啶基。
优选的,所述Ar1-Ar4的取代基为氘,卤素,硅烷基,硅氧烷基,硼基,氰基,硝基,C1-C20烷硫基,C1-C20烷氧基,C1-C20烷基,C2-C20链烯基,C2-C20炔基,C6-C20芳基,被氘取代的C6-C20芳基,芴基,C3-C20环烷基,C7-C20芳基烷基中的任一种或几种的组合。
优选的,所述L1-L5各自独立地被氘,卤素,硅烷基,硅氧烷基,硼基,氰基,硝基,C1-C20烷硫基,C1-C20烷氧基,C1-C20烷基,C2-C20链烯基,C2-C20炔基,C6-C20芳基,被氘取代的C6-C20芳基,芴基,C3-C20环烷基,C7-C20芳基烷基中的任一种或几种的组合取代或未取代。
优选的,所述式2是式1的一种特定结构。
进一步的,所述式2的化合物可以由式3-式8表示。
优选的,所述式3-式8的化合物中,X1-X3可以各自独立地为O或S。
优选的,所述式3-式8的化合物中,R1-R6各自独立地选自氢、氘、卤素、氰基、硝基、羟基、氨基;取代或非取代的C1-C60的烷基、取代或非取代的烷氧基、取代或非取代的烷胺基、取代或非取代的烷巯基取代或非取代的C3-C60的环烷基;取代或非取代的C2-C60的烯基、取代或非取代的C2-C60的炔基;取代或非取代的C6-C60芳基、取代或非取代的C7-C60的芳烷基、取代或非取代的C8-C60的芳烯基、取代或非取代的C6-C60的芳胺基或取代或非取代的C6-C60的芳巯基、取代或非取代的C2-C60的杂芳基、C10-C60的稠环基或C10-C60的螺环基。
优选的,所述式3-式8的化合物中,相邻的R1-R6之间以及R1-R6与所在环上的取代基之间可以接合或稠合在一起以形成环,所成环可以是单环也可以是多环。
优选的,所述式3-式8的化合物中,所成环优选自取代或非取代的C6-C30芳基,取代或非取代的C2-C30杂芳基。
优选的,所述式3-式8的化合物中,m、p和w中的每一个可以是0到4的整数,o、q、n中的每一个可以是0到3的整数。
优选的,所述式3-式8的化合物中,A1-A6可各自独立地选自C6-C60芳基、C3-C20杂芳基,C3-C20环烷基,C3-C20杂环烷基;优选为苯基、萘基。
优选的,所述式3-式8的化合物中,R1-R6可各自独立地被氘,卤素,硅烷基,硅氧烷基,硼基,氰基,硝基,C1-C20烷硫基,C1-C20烷氧基,C1-C20烷基,C2-C20链烯基,C2-C20炔基,C6-C20芳基,被氘取代的C6-C2芳基,芴基,含有至少一个选自O,N,S,Si和P的杂原子的C2-C20杂环基,C3-C20环烷基,C7-C20芳烷基和C8-C20芳基烯基中的任一种或几种的组合取代。
优选的,所述有机电致发光化合物的具体结构式还可以表示为:
优选的,所述式1-式8的化合物中的卤素包括氟,氯,溴或碘。
优选的,所述式1-式8的化合物中的烷基包括但不限于直链烷基,支链烷基,环烷基。
优选的,所述式1-式8的化合物中的碳原子数优选为1-40。
优选的,所述式1-式8的化合物中的烷基的具体实例包括但不限于甲基、乙基、丙基、正丙基、异丙基、丁基、正丁基、异丁基、叔丁基、仲丁基、1-甲基-丁基、1-乙基-丁基、戊基、正戊基、异戊基、新戊基、叔戊基、己基、正己基、1-甲基戊基、2-甲基戊基、4-甲基-2-戊基、3,3-二甲基丁基、2-乙基丁基、庚基、正庚基、1-甲基己基、环戊基甲基、环己基甲基、辛基、正辛基、叔辛基、1-甲基庚基、2-乙基己基、2-丙基戊基、正壬基、2,2-二甲基庚基、1-乙基-丙基、1,1-二甲基-丙基、异己基、4-甲基己基、5-甲基己基。
优选的,所述式1-式8的化合物中的烷基可被取代。
优选的,所述式1-式8的化合物中的环烷基为单环、多环和螺烷基。
优选的,所述式1-式8的化合物中的环烷基含有3-12个环碳原子。
优选的,所述式1-式8的化合物中的环烷基包括但不限于环丙基、环戊基、环己基、双环[3,1,1]庚基、螺[4,5]癸基、螺[5,5]十一烷基、金刚烷基。
优选的,所述式1-式8的化合物中的环烷基可被取代。
优选的,所述式1-式8的化合物中的烷氧基可以为线性、支化或环状。
优选的,所述式1-式8的化合物中的烷氧基含有1-40个碳原子。
优选的,所述式1-式8的化合物中的烷氧基的具体实例包括但不限于甲氧基、乙氧基、正丙氧基、异丙氧基、异丙基氧基、正丁氧基、异丁氧基、叔丁氧基、仲丁氧基、正戊氧基、新戊氧基、异戊氧基、正己氧基、3,3-二甲基丁基氧基、2-乙基丁基氧基、正辛氧基、正壬氧基、正癸氧基。
优选的,所述式1-式8的化合物中的杂环烷基指环烷基,其具有至少一个被杂原子置换的碳原子。
优选的,所述式1-式8的化合物中的杂环烷基中至少一个杂原子选自O、S、N、P、B、Si和Se。
优选的,所述式1-式8的化合物中的杂环烷基中至少一个杂原子选自O、S或N。
优选的,所述式1-式8的化合物中的杂环烷基可被取代。
优选的,所述式1-式8的化合物中的烯基为直链和支链烯基。
一种有机电致发光化合物的制备方法,制备式1化合物包括以下步骤:
S1、将通式为Sub1-1的硼酸类化合物、通式为Sub1-2的三卤代苯化合物、Pd(PPh3)4和K2CO3的混合物溶于甲苯、乙醇和水的混合溶剂中,回流12h,反应完成,冷却反应溶液的温度至室温,采用二氯甲烷萃取,水洗涤后,用无水MgSO4干燥,真空浓缩,通过柱色谱法纯化粗产物,得到通式为Sub1-3的双卤代化合物;
S2、将步骤S1得到的通式为Sub1-3的双卤代化合物、通式为Sub1-4的硼酸类化合物、Pd(PPh3)4和K2CO3的混合物溶于甲苯、乙醇和水的混合溶剂中,回流24h,反应完成,冷却反应溶液的温度至室温,采用二氯甲烷萃取,水洗涤后,用无水MgSO4干燥,真空浓缩,通过柱色谱法纯化粗产物,得到通式为Sub1-5的化合物;
S3、将三环己基膦和Pd2(dba)3加入溶剂(干燥1,4-二氧六环)中,换气3次,在氮气保护下室温搅拌30min,加入步骤S2得到的通式为Sub 1-5的化合物、联硼酸频哪醇酯,和KOAc,升温至110℃,持续搅拌24h;反应完成后,蒸馏除去1,4-二氧六环,采用二氯甲烷和水萃取,用无水MgSO4对有机相干燥,真空浓缩;通过柱色谱法对粗产物纯化、结晶,得到通式为Sub1的硼酯化合物;
S4、向通式为Sub2-1的胺类化合物和通式为Sub2-2的卤代化合物的混合溶液中加入Pd2(dba)3、P(t-Bu)3和NaOt-Bu设置温度为100℃,回流24h;用***和水萃取溶液,用无水MgSO4干燥,真空蒸发,通过硅胶柱纯化粗产物并重结晶,得到通式为Sub2-3的胺类化合物;
S5、向步骤S4得到的通式为Sub2-3的胺类化合物和通式为Sub2-4的双卤代化合物的混合溶液加入Pd2(dba)3、P(t-Bu)3和NaOt-Bu,设置温度为100℃,回流24h;用***和水萃取溶液,用无水MgSO4干燥,真空蒸发,通过硅胶柱纯化粗产物并重结晶,得到通式为Sub2的卤代胺类化合物;
S6、将得到的通式为Sub1的硼酯化合物和Sub2的卤代胺类化合物、Pd(PPh3)4和K2CO3的混合物溶于甲苯、乙醇和水的混合溶剂中,回流24h,反应完成,冷却反应溶液的温度至室温,采用二氯甲烷萃取,水洗涤后,用无水MgSO4干燥,真空浓缩,通过柱色谱法纯化粗产物,得到式1所示的化合物。
其中,上述式中Ar1-Ar4、L1-L5与权利要求1-3任一项的所述式1中相同部分表示一致。
优选的,Hal1、Hal2、Hal3代表卤素,可相同也可不同,且当Hal2和Hal3表示不同卤素时,Hal2的反应活性高于Hal3。
优选的,所述步骤S1、S2、S6中甲苯、乙醇和水的体积比为3:1:1。
一种有机电致发光化合物在有机电致发光器件中的应用,所述有机电致发光器件主要包括第一电极、第二电极、有机材料层,有机材料层包括发光层、发光辅助层材料或者包括发光层、空穴传输层材料,发光辅助层材料或空穴传输层材料采用分子结构通式由式1表示的化合物组成,发光辅助层或空穴传输层的层厚为20-25nm。
优选的,所述有机材料层包含单一种类的所述有机电致发光化合物或多种不同种类的所述有机电致发光化合物的混合物。
优选的,所述有机材料层设置在第一电极和发光层之间。
优选的,所述有机材料层包含式1-式8表示的化合物。
优选的,所述发光层包括主体材料和掺杂材料,所述主体材料和掺杂材料的重量比为95:5。
优选的,一种有机电致发光化合物的应用,所述有机电致发光器件在有机发光器件、有机太阳能电池、有机光导体、有机晶体管中的应用。
具体实施方式
下面对本发明实施例中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,本领域普通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,都属于本发明保护的范围。
实施例1
本发明实施例1公开了一种有机电致发光化合物及其制备方法,采用的技术方案如下:
S1、将20mmol通式为Sub 1-1-(1)的化合物、20mmol通式为Sub1-2-(1)的化合物、0.2mmol的Pd(PPh3)4和60mmol的K2CO3的混合物溶于150ml甲苯、50ml乙醇和50ml水的混合溶剂中,回流24h,反应完成,冷却反应溶液的温度至室温,采用二氯甲烷萃取,水洗涤后,用无水MgSO4干燥,真空浓缩,通过柱色谱法纯化粗产物,得到通式为Sub1-3-(1)的化合物,7.6g,收率85%;
S2、将步骤S1得到的通式为Sub1-3-(1)的化合物取16mmol、16mmol通式为Sub1-4-(1)的化合物、0.16mmol的Pd(PPh3)4和48mmol的K2CO3的混合物溶于150ml甲苯、50ml乙醇和50ml水的混合溶剂中,回流24h,反应完成,冷却反应溶液的温度至室温,采用二氯甲烷萃取,水洗涤后,用无水MgSO4干燥,真空浓缩,通过柱色谱法纯化粗产物,得到通式为Sub1-5-(1)的化合物,8.04g,收率80%;
S3、将三环己基膦和0.12mmol的Pd2(dba)3加入300ml溶剂(干燥1,4-二氧六环)中,换气3次,在氮气保护下室温搅拌30min,加入步骤S2得到的通式为Sub 1-5-(1)的化合物12.0mmol、13.2mmol的联硼酸频哪醇酯,和36.0mmol的KOAc,升温至110℃,持续搅拌24h;反应完成后,蒸馏除去1,4-二氧六环,采用二氯甲烷和水萃取),用无水MgSO4对有机相干燥,真空浓缩;通过柱色谱法对粗产物纯化、结晶,得到通式为Sub1-(1)的化合物,7.35g,收率85%;
S4、向20mmol通式为Sub2-1-(1)的化合物和20mmol通式为Sub2-2-(1)的化合物的混合溶液中加入0.2mmol的Pd2(dba)3、2mmol的PPh3和60mmol的NaOt-Bu,设置温度为100℃,回流24h;用***和水萃取溶液,用无水MgSO4干燥,真空蒸发,通过硅胶柱纯化粗产物并重结晶,得到通式为Sub2-3-(1)的化合物,2.8g,收率83%;
S5、向步骤S4得到的通式为Sub2-3-(1)的化合物16mmol和17mmol通式为Sub2-4-(1)的化合物的混合溶液加入0.16mmol的Pd2(dba)3、1.6mmol的PPh3和48mmol的NaOt-Bu,设置温度为100℃,回流24h;用***和水萃取溶液,用无水MgSO4干燥,真空蒸发,通过硅胶柱纯化粗产物并重结晶,得到通式为Sub 2-(1)的化合物4.13g,收率80%;
S6、将得到的通式为Sub1的化合物1.0eq和Sub2的化合物1.1eq,0.01eq的Pd(PPh3)4和3.0eq的K2CO3的混合物加入到甲苯/乙醇/水的混合溶剂中,回流24h,反应完成,分液,水相用***和水萃取,合并有机相,用无水MgSO4干燥,蒸发,通过硅胶柱纯化粗产物并重结晶,得到最终产物化合物1,8.54g,收率85%。
其中,合成出的Sub 1-(1)的具体结构包括但不限于如下表1,其质谱数据如表2所示。
表1
表2
化合物 | FD-MS |
Sub 1-(1) | m/z=720.17(C48H37BO2S2=720.23) |
Sub 1-(7) | m/z=720.29(C48H37BO2S2=720.23) |
Sub 1-(10) | m/z=688.42(C48H37BO4=688.28) |
Sub 1-(20) | m/z=628.19(C42H33BO3S=628.22) |
Sub 1-(21) | m/z=628.71(C42H33BO3S=628.22) |
Sub 1-(34) | m/z=643.97(C42H33BO2S2=644.20) |
Sub 1-(39) | m/z=628.35(C42H33BO3S=628.22) |
Sub 1-(41) | m/z=462.07(C30H27BO2S=462.18) |
Sub 1-(49) | m/z=578.83(C39H35BO2S=578.25) |
Sub 1-(55) | m/z=598.31(C42H35BO3=598.27) |
合成出的Sub 2-(1)的具体结构包括但不限于如下表3,其质谱数据如表4所示。
表3
表4
化合物 | FD-MS |
Sub 2-(1) | m/z=323.8(C18H14BrN=323.03) |
Sub 2-(7) | m/z=339.62(C48H37BO2S2=399.06) |
Sub 2-(10) | m/z=439.77(C27H22BrN=439.09) |
Sub 2-(17) | m/z=475.11(C30H22BrN=475.09) |
Sub 2-(20) | m/z=373.21(C22H16BrN=373.05) |
Sub 2-(25) | m/z=489.57(C30H20BrNO=489.07) |
Sub 2-(39) | m/z=489.23(C30H20BrNO=489.07) |
Sub 2-(41) | m/z=505.08(C30H20BrNS=505.05) |
Sub 1-(55) | m/z=565.71(C36H24BrNO=565.10) |
合成出的中间体及最终产物的具体结构包括但不限于如下表5,其质谱数据如表6所示。
表5
表6
化合物 | FD-MS |
1 | m/z=837.55(C60H39NS2=837.25) |
7 | m/z=913.01(C66H43NS2=913.28) |
10 | m/z=921.37(C69H47NO2=921.36) |
17 | m/z=912.81(C66H43NS2=913.28) |
20 | m/z=795.42(C58H37NOS=795.26) |
21 | m/z=821.64(C60H39NOS=821.28) |
25 | m/z=971.25(C72H45NO3=971.34) |
34 | m/z=927.62(C66H41NOS2=927.26) |
39 | m/z=911.67(C66H41NO2S=911.29) |
41 | m/z=761.19(C54H35NS2=761.22) |
49 | m/z=877.78(C63H43NS2=877.28) |
55 | m/z=957.27(C72H47NO2=957.36) |
实施例2
本发明实施例2公开了有机电致发光化合物在有机电致发光器件中的应用,所述有机电致发光器件的制备方法,采用的技术方案如下:
器件实施例(1):制造含有实施例1最终产物化合物1的有机电致发光器件
将涂层厚度为的ITO玻璃基板放在蒸馏水中清洗2次,超声波洗涤30分钟,用蒸馏水反复清洗2次,超声波洗涤10分钟,蒸馏水清洗结束后,异丙醇、丙酮、甲醇等溶剂按顺序超声波洗涤以后干燥,转移到等离子体清洗机里,将上述基板洗涤5分钟,送到蒸镀机里。将已经准备好的ITO透明电极上蒸镀厚度为30nm的4,4',4”-三[2-萘基苯基氨基]三苯基胺(2-TNATA)作为空穴注入层。然后将化合物1在形成的空穴注入层上面真空蒸镀厚度为20nm的空穴传输层。然后在上述空穴传输层上蒸镀厚度为20nm的4,4'-N,N'-联苯二咔唑("CBP")和掺杂材料Ir(bty)2acac。主体材料和掺杂材料的重量比为95:5。接着在上述发光层上真空蒸镀厚度为30nm的TPBi作为空穴阻挡层及电子传输层。在上述电子传输层上真空蒸镀厚度为0.5nm氟化锂(LiF),作为电子注入层。最后蒸镀厚度为100nm的铝作为阴极,以此完成了有机电致发光器件的制备。对得到的器件的性能发光特性测试。
器件实施例(2)-器件实施例(12):
将器件实施例(1)中的有机电致发光化合物的化合物1分别置换为化合物7、10、17、20、21、25、34、39、41、49、55,其他方法相同,分别制作含有化合物7、10、17、20、21、25、34、39、41、49、55的有机电致发光器件。
器件对比例(1):制造含有对比化合物1的有机电致发光器件。按照器件实施例(1)的方法,将空穴传输层的材料由化合物1置换为对比化合物1,其他方法相同,制作含有对比化合物1的有机电致发光器件。
器件对比例(2):制造含有对比化合物2的有机电致发光器件。按照器件实施例(1)的方法,将空穴传输层的材料由化合物1置换为对比化合物2,其他方法相同,制作含有对比化合物2的有机电致发光器件。
表7为本发明器件实施例(1)-器件实施例(12)与器件对比例(1)、器件对比例(2)制备的有机电致发光器件的发光特性测试结果(亮度值为5000cd/m2)。
表7
由表7可以看出,使用本发明提供化合物作为空穴传输层材料所制备的有机电致发光器件与使用比较化合物1和对比化合物1作为空穴传输材料所制备的有机电致发光器件相比,驱动电压以及电流密度明显降低,发光效率以及寿命得到显著提高。
器件实施例(13)
将涂层厚度为的ITO玻璃基板放在蒸馏水中清洗2次,超声波洗涤30分钟,用蒸馏水反复清洗2次,超声波洗涤10分钟,蒸馏水清洗结束后,异丙醇、丙酮、甲醇等溶剂按顺序超声波洗涤以后干燥,转移到等离子体清洗机里,将上述基板洗涤5分钟,送到蒸镀机里。将已经准备好的ITO透明电极上蒸镀厚度为50nm的4,4',4”-三[2-萘基苯基氨基]三苯基胺(2-TNATA)作为空穴注入层。然后将NPB在形成的空穴注入层上面真空蒸镀厚度为50nm的空穴传输层。在上述空穴传输层上蒸镀厚度为20nm的化合物1作为发光辅助层;然后在上述发光辅助层上蒸镀厚度为20nm的4,4'-N,N'-联苯二咔唑("CBP")和掺杂材料Ir(ppy)3。主体材料和掺杂材料的重量比为97:3。接着在上述发光层上真空蒸镀厚度为30nm的TPBi作为空穴阻挡层及电子传输层。在上述电子传输层上真空蒸镀厚度为0.5nm氟化锂(LiF),作为电子注入层。最后蒸镀厚度为100nm的铝作为阴极,以此完成了有机电致发光器件的制备。
器件实施例(14)-器件实施例(24)
将器件实施例(13)中发光辅助层的化合物1分别置换为化合物7、10、17、20、21、25、34、39、41、49、55,其他方法相同,分别制作含有化合物7、10、17、20、21、25、34、39、41、49、55的有机电致发光器件。
器件对比例(3):制造含有对比化合物2的有机电致发光器件。按照器件实施例(13)的方法,将发光辅助层的化合物1置换为对比化合物2,其他方法相同,制作含有对比化合物2的有机电致发光器件。
器件对比例(4):按照器件实施例(13)的方法,制作器件对比例(3)。不同之处在于不含有发光辅助层。
表8为本发明器件实施例(13)-器件实施例(24)与器件对比例(3)、器件对比例(4)制备的有机电致发光器件的发光特性测试结果(亮度值为5000cd/m2)。
表8
由表8可以看出,使用本发明提供化合物作为发光辅助层材料所制备的有机电致发光器件与使用对比化合物2作为发光辅助层材料以及不使用发光辅助层的有机电致发光器件相比,驱动电压以及电流密度明显降低,发光效率以及寿命得到显著提高。
本领域的技术人员将明显看到,在不脱离本发明的精神和范围下,本发明可以有许多修改和变化。因此可以预期到,本发明覆盖在附带权利要求的范围及其相当范围内提供的本发明修改和变化。
本说明书中各个实施例采用递进的方式描述,每个实施例重点说明的都是与其他实施例的不同之处,各个实施例之间相同相似部分互相参见即可。
对所公开的实施例的上述说明,使本领域专业技术人员能够实现或使用本发明。对这些实施例的多种修改对本领域的专业技术人员来说将是显而易见的,本文中所定义的一般原理可以在不脱离本发明的精神或范围的情况下,在其它实施例中实现。因此,本发明将不会被限制于本文所示的这些实施例,而是要符合与本文所公开的原理和新颖特点相一致的最宽的范围。
Claims (5)
2.一种权利要求1所述的有机电致发光化合物的制备方法,其特征在于,制备所述化合物包括以下步骤:
S1、将通式为Sub1-1的硼酸类化合物、通式为Sub1-2的三卤代苯化合物、Pd(PPh3)4和K2CO3的混合物溶于甲苯、乙醇和水的混合溶剂中,回流12h,反应完成,冷却反应溶液的温度至室温,采用二氯甲烷萃取,水洗涤后,用无水MgSO4干燥,真空浓缩,通过柱色谱法纯化粗产物,得到通式为Sub1-3的双卤代化合物;
S2、将步骤S1得到的通式为Sub1-3的双卤代化合物、通式为Sub1-4的硼酸类化合物、Pd(PPh3)4和K2CO3的混合物溶于甲苯、乙醇和水的混合溶剂中,回流24h,反应完成,冷却反应溶液的温度至室温,采用二氯甲烷萃取,水洗涤后,用无水MgSO4干燥,真空浓缩,通过柱色谱法纯化粗产物,得到通式为Sub1-5的化合物;
S3、将三环己基膦和Pd2(dba)3加入溶剂(干燥1,4-二氧六环)中,换气3次,在氮气保护下室温搅拌30min,加入步骤S2得到的通式为Sub 1-5的化合物、联硼酸频哪醇酯,和KOAc,升温至110℃,持续搅拌24h;反应完成后,蒸馏除去1,4-二氧六环,采用二氯甲烷和水萃取,用无水MgSO4对有机相干燥,真空浓缩;通过柱色谱法对粗产物纯化、结晶,得到通式为Sub1的硼酯化合物;
S4、向通式为Sub2-1的胺类化合物和通式为Sub2-2的卤代化合物的混合溶液中加入Pd2(dba)3、P(t-Bu)3和NaOt-Bu设置温度为100℃,回流24h;用***和水萃取溶液,用无水MgSO4干燥,真空蒸发,通过硅胶柱纯化粗产物并重结晶,得到通式为Sub2-3的胺类化合物;
S5、向步骤S4得到的通式为Sub2-3的胺类化合物和通式为Sub2-4的双卤代化合物的混合溶液加入Pd2(dba)3、P(t-Bu)3和NaOt-Bu,设置温度为100℃,回流24h;用***和水萃取溶液,用无水MgSO4干燥,真空蒸发,通过硅胶柱纯化粗产物并重结晶,得到通式为Sub 2的卤代胺类化合物;
S6、将得到的通式为Sub1的硼酯化合物和Sub2的卤代胺类化合物、Pd(PPh3)4和K2CO3的混合物溶于甲苯、乙醇和水的混合溶剂中,回流24h,反应完成,冷却反应溶液的温度至室温,采用二氯甲烷萃取,水洗涤后,用无水MgSO4干燥,真空浓缩,通过柱色谱法纯化粗产物,得到所述化合物;
其中,上述式中Ar1-Ar4、L1-L5与权利要求1所述化合物中相同部分表示一致。
3.根据权利要求2所述的一种有机电致发光化合物的制备方法,其特征在于,所述步骤S1、S2、S6中甲苯、乙醇和水的体积比为3:1:1。
4.一种权利要求1所述的有机电致发光化合物在有机电致发光器件中的应用,其特征在于,所述有机电致发光器件主要包括第一电极、第二电极、有机材料层,有机材料层包括发光层、发光辅助层材料或者包括发光层、空穴传输层材料,发光辅助层材料或空穴传输层材料采用权利要求1所述化合物,发光辅助层或空穴传输层的层厚为20-25nm。
5.根据权利要求4所述的一种有机电致发光化合物在有机电致发光器件中的应用,其特征在于,所述发光层包括主体材料和掺杂材料,所述主体材料和掺杂材料的重量比为95:5。
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