CN108358918A - 一种芘衍生物及其有机电致发光器件 - Google Patents
一种芘衍生物及其有机电致发光器件 Download PDFInfo
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- CN108358918A CN108358918A CN201810378387.2A CN201810378387A CN108358918A CN 108358918 A CN108358918 A CN 108358918A CN 201810378387 A CN201810378387 A CN 201810378387A CN 108358918 A CN108358918 A CN 108358918A
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- pyrene derivatives
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- organic
- electroluminescence device
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- 150000003220 pyrenes Chemical class 0.000 title claims abstract description 23
- 238000005401 electroluminescence Methods 0.000 title claims abstract description 16
- 239000000463 material Substances 0.000 claims abstract description 36
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 11
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 7
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 5
- 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 5
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical class C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 5
- 125000005561 phenanthryl group Chemical group 0.000 claims description 5
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 5
- 125000001725 pyrenyl group Chemical group 0.000 claims description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 4
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000006743 (C1-C60) alkyl group Chemical group 0.000 claims description 3
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 3
- CRXBTDWNHVBEIC-UHFFFAOYSA-N 1,2-dimethyl-9h-fluorene Chemical class C1=CC=C2CC3=C(C)C(C)=CC=C3C2=C1 CRXBTDWNHVBEIC-UHFFFAOYSA-N 0.000 claims description 2
- QTPLEVOKSWEYAC-UHFFFAOYSA-N 1,2-diphenyl-9h-fluorene Chemical class C=1C=CC=CC=1C1=C2CC3=CC=CC=C3C2=CC=C1C1=CC=CC=C1 QTPLEVOKSWEYAC-UHFFFAOYSA-N 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 abstract description 12
- 150000001875 compounds Chemical class 0.000 abstract description 10
- 239000011368 organic material Substances 0.000 abstract description 7
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 abstract description 6
- 230000008901 benefit Effects 0.000 abstract description 5
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 abstract description 3
- 230000009477 glass transition Effects 0.000 abstract description 3
- 238000010189 synthetic method Methods 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 35
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000000047 product Substances 0.000 description 16
- -1 triazine radical Chemical class 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 13
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
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- 229910052757 nitrogen Inorganic materials 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
- YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 2
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 2
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 2
- 125000006749 (C6-C60) aryl group Chemical group 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
- VKLKXFOZNHEBSW-UHFFFAOYSA-N 5-[[3-[(4-morpholin-4-ylbenzoyl)amino]phenyl]methoxy]pyridine-3-carboxamide Chemical compound O1CCN(CC1)C1=CC=C(C(=O)NC=2C=C(COC=3C=NC=C(C(=O)N)C=3)C=CC=2)C=C1 VKLKXFOZNHEBSW-UHFFFAOYSA-N 0.000 description 2
- RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 description 2
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- PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 description 2
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- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound 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 2
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- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
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- DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 description 1
- SZWWISYJSCLLFW-UHFFFAOYSA-N Nc1cc(-c2cccc3ccccc23)ccn1 Chemical compound Nc1cc(-c2cccc3ccccc23)ccn1 SZWWISYJSCLLFW-UHFFFAOYSA-N 0.000 description 1
- BAOIJCGWLQNKOE-UHFFFAOYSA-N Nc1cc(-c2ccccc2)ccn1 Chemical compound Nc1cc(-c2ccccc2)ccn1 BAOIJCGWLQNKOE-UHFFFAOYSA-N 0.000 description 1
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- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 1
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- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- BZLZKLMROPIZSR-UHFFFAOYSA-N triphenylsilicon Chemical compound C1=CC=CC=C1[Si](C=1C=CC=CC=1)C1=CC=CC=C1 BZLZKLMROPIZSR-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
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Abstract
本发明提供一种芘衍生物及其有机电致发光器件，属于有机光电材料技术领域。该化合物具有式(Ⅰ)所示结构，本发明将芘与苯并咪唑进行稠合，使得到的材料具有优异的电子传输能力和高玻璃化转变温度并且能够防止结晶的作用；合成方法简单易操作，使用该芘衍生物制备的有机发光器件表现出驱动电压低、发光效率高的优点，是性能优良的有机发光材料。
Description
技术领域
本发明涉及有机光电材料技术领域，具体涉及一种芘衍生物及其有机电致发光器件。
背景技术
随着信息产业的进步，传统的显示器已不能满足人们的要求，如：阴极射线管(cathode ray tube,CRT)显示器体积大、驱动电压高；液晶显示器(liquid crystaldisplay,LCD)亮度低、视角窄、工作温度范围小；等离子显示器(plasma display panel,PDP)造价昂贵、分辨率不高、耗电量大。
有机电致发光二极管(organic light-emitting diodes,OLEDs)作为一种全新的显示技术在各个性能上拥有现有显示技术无以伦比的优势，如具有全固态、自主发光、亮度高、高分辨率、视角宽(170度以上)、响应速度快、厚度薄、体积小、重量轻、可使用柔性基板、低电压直流驱动(3-10V)、功耗低、工作温度范围宽等，使得它的应用市场十分广泛，如照明系统、通讯系统、车载显示、便携式电子设备、高清晰度显示甚至是军事领域。
有机电致发光材料在近些年内不断实现突破，取得了令人瞩目的进展，对传统的显示材料构成了强有力的挑战。柔性OLED商业化以后，目前世界上与之相关的科研及商业力量都在不遗余力的开展这方面的工作。虽然有机电致发光材料研究已经取得巨大的成果，但是OLED在商业化的过程中还有一些亟待解决的问题。
发光材料分为荧光材料和磷光材料，发光层的形成方法是荧光主体材料中掺杂磷光材料(有机金属)的方法和荧光主体材料掺杂荧光(包含氮的有机物)掺杂剂的方法。常用的主体材料概可以分为几种，如空穴传输主体材料、电子传输主体材料、双极主体材料、惰性主体材料、荧光配合物主体材料和磷光配合物主体材料。
在使用磷光材料制备的有机发光器件中，大多使用TPD等含有三苯胺基团材料当作发光层的主体发光材料。然而，这一类材料的热稳定性较差，导致使用磷光材料的有机发光器件的寿命较短，因而降低了此类材料的使用程度。如何设计新的性能更好的材料进行调节，一直是本领域技术人员亟待解决的问题。
发明内容
本发明的目的是提供一种芘衍生物及其有机电致发光器件，本发明通过对芘与苯并咪唑进行稠合，使得到的材料具有高玻璃化转变温度并且能够防止结晶的作用。将该化合物作为发光层中的主体材料使用而制成的有机电致发光器件，表现出驱动电压低、发光效率高的优点，是性能优良的有机发光材料。
本发明首先提供一种芘衍生物，结构式为：
其中，R1、R2独立的选自氢、取代或未取代的C1-C60烷基、取代或未取代的C6-C60的芳基、取代或未取代的C3～C60的杂芳基中的一种。
优选的，所述的R1、R2独立的选自氢、取代或未取代的C1-C30烷基、取代或未取代的C6-C30的芳基、取代或未取代的C4～C30的杂芳基中的一种。
优选的，所述的R1、R2独立的选自氢、C1～C4烷基或取代或未取代的如下基团：苯基、萘基、蒽基、菲基、芘基、联苯基、三联苯基、芴基、9-9二甲基芴、9-9二苯基芴、螺二芴基、咔唑基、吡啶基、吖啶基、吩噻嗪基、吩噁嗪基、三嗪基、二苯并噻吩基、二苯并呋喃基、喹啉基或异喹啉基。
优选的，所述的芘衍生物选自如下所示结构中的任意一种：
。
本发明还提供一种有机电致发光器件，包括阳极、阴极以及位于所述阳极与所述阴极之间的若干个有机功能层，所述有机功能层中包括所述的芘衍生物任意一种或至少两种的组合。
优选的，所述有机功能层包括发光层，所述发光层包括所述的芘衍生物的任意一种或至少两种的组合。
优选的，所述芘衍生物在发光层中用作主体材料。
本发明的有益效果：
为了解决现有技术中磷光主体材料的热稳定性较差，使用寿命短等问题，本发明首先提供一种含有芘和苯并咪唑结构的衍生物，该化合物具有式(Ⅰ)所示结构。本发明将芘与苯并咪唑进行稠合，并且用烷基、芳基、杂芳基对芘和苯并咪唑进行取代，改善了主体材料的电子传输性能，使得所述材料在电子传输方面是高效的，可改善器件的电流特性，使得到的材料具有高玻璃化转变温度并且能够防止结晶的作用。将该化合物作为发光层中的主体材料使用而制成的有机电致发光器件，表现出驱动电压低、发光效率高的优点，是性能优良的有机发光材料。
具体实施方式
为了进一步理解本发明，下面结合实施例对本发明优选实施方案进行描述，但是应当理解，这些描述只是为进一步说明本发明的特征和优点，而不是对本发明权利要求的限制。
需要说明的是，除非另有规定，本发明所使用的科技术语的含义与本领域技术人员通常所理解的含义相同。
本发明所述烷基是指烷烃分子中少掉一个氢原子而成的烃基，其可以为直链烷基、支链烷基或环烷基，实例可包括甲基、乙基、丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、戊基、异戊基、环戊基、环己基等，但不限于此。
本发明所述芳基是指芳烃分子的芳核碳上去掉一个氢原子后，剩下一价基团的总称，其可以为单环芳基或稠环芳基，实例可包括苯基、联苯基、萘基、蒽基、菲基或芘基等，但不限于此。
本发明所述杂芳基是指芳基中一个或多个芳核碳被杂原子替代得到的基团的总称，所述杂原子包括但不限于氧、硫、氮或硅原子，所述杂芳基可以为单环或稠环，实例可包括吡啶基、吩噻嗪基、吩恶嗪基、嘧啶基、苯并嘧啶基、咔唑基、三嗪基、苯并噻唑基、苯并咪唑基、吖啶基等，但不限于此。
本发明所述取代的烷基、取代的芳基、取代的杂芳基中，所述取代基可以独立的选自氘原子、氰基、硝基、卤素原子、C1-C10的烷基、C1-C10的烷氧基、C1-C10的烷硫基、C1-C30的芳基、C1-C30的芳氧基、C1-C30的芳硫基、C3-C30的杂芳基，C1～C30的硅烷基、C2～C10的烷胺基、C6～C30的芳胺基等，例如氘原子、氰基、硝基、卤素、甲基、乙基、丙基、异丙基、叔丁基、甲氧基、甲硫基、苯基、联苯基、三联苯基、萘基、蒽基、菲基、苯并菲基、苝基、芘基、芴基、9,9-二甲基芴基、苯甲基、苯氧基、苯硫基、二苯胺基、二甲胺基、咔唑基、9-苯基咔唑基、呋喃基、噻吩基、三苯基硅基、三甲基硅基、三氟甲基、吩噻嗪基、吩噁嗪基、吖啶基、哌啶基、吡啶基、吡嗪基、三嗪基、嘧啶基等，但不限于此。
本发明首先提供一种芘衍生物，具有如式(I)所示的结构式：
其中，R1、R2独立的选自氢、取代或未取代的C1-C60烷基、取代或未取代的C6-C60的芳基、取代或未取代的C3～C60的杂芳基中的一种。
按照本发明，优选R1、R2独立的选自氢、取代或未取代的C1-C30烷基、取代或未取代的C6-C30的芳基、取代或未取代的C4～C30的杂芳基中的一种。
按照本发明，优选R1、R2独立的选自氢、C1～C4烷基或取代或未取代的如下基团：苯基、萘基、蒽基、菲基、芘基、联苯基、三联苯基、芴基、螺二芴基、咔唑基、吡啶基、吖啶基、吩噻嗪基、吩噁嗪基、三嗪基、二苯并噻吩基、二苯并呋喃基、喹啉基或异喹啉
具体的，所述芘衍生物优选选自如下结构中的任意一种：
。
以上列举了本发明所述芘衍生物的一些具体的结构形式，但本发明并不局限于所列的这些化学结构，凡是以式(I)所示结构为基础，R1、R2为如上所限定的基团都应该包含在内。
本发明所述菲衍生物，其制备方法如下：
按照本发明，中间体A按照如下所示方法制备得到：
在氮气的保护下，化合物a和化合物b，以Pd(PPh3)4作为催化剂，发生C-C偶联反应生成化合物c，以叔丁醇钠、醋酸钯、三叔丁基膦作为催化剂，化合物c与化合物d发生C-N偶联反应生成中间体A。
按照本发明，化合物I按照如下所示方法制备得到：
将中间体A溶解于水中，将PhI(OAc)2，mCPBA和PTSA.H2O加入上述溶液中，搅拌至反应完全，得到化合物I。
本发明还提供一种有机电致发光器件，所述有机电致发光器件为本领域技术人员所熟知的有机电致发光器件即可，本发明所述有机电致发光器件包括阳极、阴极以及位于所述阳极与阴极之间的若干个有机功能层，所述有机功能层中包括所述的菲衍生物任意一种或至少两种的组合。所述有机功能层可以包括空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层与电子注入层中的至少一层，优选所述有机功能层包括发光层，所述发光层包括所述的芘衍生物的任意一种或至少两种的组合。更优选所述芘衍生物在发光层中用作主体材料。
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。
实施例1：
化合物2的制备
中间体2-3的制备
在氮气的保护下，向2L反应釜中加入2-1(36.00g，100.00mmol)，2-2(12.20g，100.00mmol)，碳酸钾(1.24g，9.00mmol)，甲苯200mL搅拌。反应釜内温度升到70℃，加入Pd(PPh3)4(1.04g，0.90mmol)，蒸馏水100mL搅拌，搅拌回流11h，充分反应。加入70mL蒸馏水终止反应后，减压过滤，用蒸馏水洗涤固体，然后用丙酮，甲苯，THF来重结晶，得到固体后再升华，甲苯重结晶，得到中间体2-3 28.69g，产率为80.32％。
中间体2-5的制备
将三叔丁基膦(4.4mL的1.0M的甲苯溶液，1.48g，0.05mmol)、醋酸钯(0.4g，1.83mmol)和叔丁醇钠(52.7g，549mmol)添加至2-3(28.69g，80.31mmol)和2-4(7.56g，80.31mmol)在脱气甲苯(500mL)中的溶液，并且将该混合物在回流下加热2小时。将该反应混合物冷却至室温，用甲苯稀释并且经由硅藻土过滤。将该滤液用水稀释，并用甲苯提取，并且合并有机相，将其在真空下进行蒸发。将该残余物经由硅胶(庚烷/二氯甲烷)进行过滤，并从异丙醇中结晶，得到中间体2-5 23.39g，产率为78.63％。
化合物2的制备
将2-5(23.39g，63.13mmol)溶解于1L水中，将PhI(OAc)2(1.87g，5.8mmol)，mCPBA(10equiv，2.9mmol)和PTSA.H2O(20equiv，5.88mmol)加入上述溶液中，室温下敞口在空气中充分搅拌4-6h，TLC监测直到反应物反应完全，反应溶液用乙酸乙酯进行萃取，用饱和硫代硫酸钠溶液洗涤产物，有机层用饱和盐水洗涤，并且用无水硫酸钠干燥，对有机提取物进行减压抽滤，重结晶得到217.60g，产率为75.65％。质谱m/z：368.44(计算值：368.45)。理论元素含量(％)C27H16N2：C，88.02；H，4.38；N，7.60实测元素含量(％)：C，88.03；H，4.37；N，7.59。上述证实获得产物为目标产物2。
实施例2
化合物12的制备
将实施例1中的2-2替换为如上所示12-2，得到化合物12。质谱m/z：458.52(计算值：458.53)。理论元素含量(％)C33H18N2O：C，86.44；H，3.96；N，6.11；O，3.49实测元素含量(％)：C，86.45；H，3.97；N，6.12；O，3.48。上述证实获得产物为目标产物12。
实施例3
化合物19的制备
将实施例1中的2-2替换为如上所示19-2，2-4替换为如上所示19-4，得到化合物19。质谱m/z：533.63(计算值：533.64)。理论元素含量(％)C39H23N3：C，87.78；H，4.34；N，7.87实测元素含量(％)：C，87.79；H，4.35；N，7.86。上述证实获得产物为目标产物19。
实施例4
化合物28的制备
将实施例1中的2-2替换为如上所示28-2，2-4替换为如上所示28-4，得到化合物28。质谱m/z：561.64(计算值：561.65)。理论元素含量(％)C40H23N3O：C，85.54；H，4.13；N，7.48；O，2.85实测元素含量(％)：C，85.53；H，4.14；N，7.47；O，2.86。上述证实获得产物为目标产物28。
实施例5
化合物33的制备
将实施例1中的2-2替换为如上所示33-2，2-4替换为如上所示33-4，得到化合物33。质谱m/z：544.66(计算值：544.67)。理论元素含量(％)C41H24N2：C，90.41；H，4.44；N，5.14实测元素含量(％)：C，90.42；H，4.43；N，5.12。上述证实获得产物为目标产物33。
实施例6
化合物48的制备
将实施例1中的2-2替换为如上所示48-2，2-4替换为如上所示48-4得到化合物48。质谱m/z：625.73(计算值：625.74)。理论元素含量(％)C45H27N3O：C，86.38；H，4.35；N，6.72；O，2.56实测元素含量(％)：C，86.39；H，4.36；N，6.73；O，2.57。上述证实获得产物为目标产物48。
实施例7
化合物67的制备
将实施例1中的2-2替换为如上所示67-2，2-4替换为如上所示67-4，得到化合物67。质谱m/z：734.90(计算值：734.91)。理论元素含量(％)C56H34N2：C，91.52；H，4.66；N，3.81实测元素含量(％)：C，91.53；H，4.65；N，3.82。上述证实获得产物为目标产物67。
实施例8
化合物86的制备
将实施例1中的2-2替换为如上所示86-2，2-4替换为如上所示86-4得到化合物86。质谱m/z：650.75(计算值：650.76)。理论元素含量(％)C45H26N6：C，83.06；H，4.03；N，12.91实测元素含量(％)：C，83.07；H，4.04；N，12.92。上述证实获得产物为目标产物86。
[对比应用实施例]
将透明阳极电极ITO基板分别用去离子水、丙酮、乙醇超声清洗各15分钟，然后在等离子清洗器中清洗2分钟，干燥并且抽真空至5×10-5Pa。随后将处理后的ITO基板进行蒸镀。首先蒸镀一层HAT-CN作为空穴传输层，蒸镀速率为0.1nm/s，蒸镀厚度为10nm。然后是发光层的蒸镀，混合蒸镀所述有机发光材料CBP/Ir(ppy)3，作为绿光磷光掺杂材料，掺杂浓度为5％，蒸镀速率为0.005nm/s，蒸镀厚度为30nm，随后蒸镀50nm的TPBI作为电子传输层，蒸镀速率为0.01nm/s，在电子传输层上真空蒸镀Al层作为阴极，厚度为30nm。
[应用实施例1-8]
将透明阳极电极ITO基板分别用去离子水、丙酮、乙醇超声清洗各15分钟，然后在等离子清洗器中清洗2分钟，干燥并且抽真空至5×10-5Pa，随后将处理后的ITO基板进行蒸镀。首先蒸镀一层HAT-CN作为空穴传输层，蒸镀速率为0.1nm/s，蒸镀厚度为10nm。然后是发光层的蒸镀，混合蒸镀本发明所述芘衍生物/Ir(ppy)3，作为绿光磷光掺杂材料，掺杂浓度为5％，蒸镀速率为0.005nm/s，蒸镀厚度为30nm，随后蒸镀50nm的50nm的TPBI作为电子传输层，蒸镀速率为0.01nm/s，在电子传输层上真空蒸镀Al层作为阴极，厚度为30nm。上述方法制造的有机发光器件的电子发光特性在下表中表示：
以上结果表明，本发明的化合物作为发光层主体材料，应用于有机电致发光器件中，发光效率高，是性能良好的有机发光材料。
虽然本发明用示范性实施方案进行了特别的描述，但应该理解在不偏离权利要求所限定的本发明的精神与范围的情况下，本领域普通技术人员可对其进行各种形式和细节上的改变。
Claims (7)
1.一种芘衍生物，其特征在于，具有如下通式(Ⅰ)所示结构：
其中，R1、R2独立的选自氢、取代或未取代的C1-C60烷基、取代或未取代的C6-C60的芳基、取代或未取代的C3-C60的杂芳基中的一种。
2.根据权利要求1所述芘衍生物，其特征在于，R1、R2独立的选自氢、取代或未取代的C1-C30烷基、取代或未取代的C6-C30的芳基、取代或未取代的C4-C30的杂芳基中的一种。
3.根据权利要求1所述芘衍生物，其特征在于，R1、R2独立的选自氢、C1-C4烷基或取代或未取代的如下基团：苯基、萘基、蒽基、菲基、芘基、联苯基、三联苯基、芴基、9-9二甲基芴、9-9二苯基芴、螺二芴基、咔唑基、吡啶基、吖啶基、吩噻嗪基、吩噁嗪基、三嗪基、二苯并噻吩基、二苯并呋喃基、喹啉基或异喹啉基。
4.根据权利要求1所述芘衍生物，其特征在于，选自如下所示结构中的任意一种：
5.一种有机电致发光器件，包括阳极、阴极以及位于所述阳极与所述阴极之间的若干个有机功能层，其特征在于,所述有机功能层中包括权利要求1～4任一项所述的芘衍生物任意一种或至少两种的组合。
6.根据权利要求5所述的一种有机电致发光器件，其特征在于，所述有机功能层包括发光层，所述发光层包括权利要求1～4任一项所述的芘衍生物的任意一种或至少两种的组合。
7.根据权利要求6所述的一种有机电致发光器件，其特征在于，所述芘衍生物在发光层中用作主体材料。
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107602440A (zh) * | 2017-10-09 | 2018-01-19 | 长春海谱润斯科技有限公司 | 一种苯并咔唑类有机电致发光材料及其有机发光器件 |
| CN107629062A (zh) * | 2017-10-09 | 2018-01-26 | 长春海谱润斯科技有限公司 | 一种咔唑类衍生物及其有机发光器件 |
| CN107698486A (zh) * | 2017-10-09 | 2018-02-16 | 长春海谱润斯科技有限公司 | 一种苯并咔唑有机化合物及其有机发光器件 |
| CN107698488A (zh) * | 2017-10-09 | 2018-02-16 | 长春海谱润斯科技有限公司 | 一种苯并咔唑类衍生物及其有机发光器件 |
| CN108358919A (zh) * | 2018-04-25 | 2018-08-03 | 长春海谱润斯科技有限公司 | 一种菲衍生物及其有机电致发光器件 |
| CN108440524A (zh) * | 2018-04-25 | 2018-08-24 | 长春海谱润斯科技有限公司 | 一种三亚苯衍生物及其有机电致发光器件 |
Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20100099459A (ko) * | 2009-03-03 | 2010-09-13 | 덕산하이메탈(주) | 비스벤조이미다졸 화합물 및 이를 이용한 유기전기소자, 그단말 |
| WO2012079032A2 (en) * | 2010-12-09 | 2012-06-14 | Trana Discovery, Inc. | Compositions and methods of treating drug-resistant retroviral infections |
| JP2012204794A (ja) * | 2011-03-28 | 2012-10-22 | Sony Corp | 有機電界発光素子および表示装置 |
| CN106467549A (zh) * | 2016-08-03 | 2017-03-01 | 江苏三月光电科技有限公司 | 一种含有苯并咪唑的化合物及其在有机电致发光器件上的应用 |
| CN108358919A (zh) * | 2018-04-25 | 2018-08-03 | 长春海谱润斯科技有限公司 | 一种菲衍生物及其有机电致发光器件 |
| CN108440524A (zh) * | 2018-04-25 | 2018-08-24 | 长春海谱润斯科技有限公司 | 一种三亚苯衍生物及其有机电致发光器件 |
| CN108440525A (zh) * | 2018-04-25 | 2018-08-24 | 长春海谱润斯科技有限公司 | 一种苝衍生物及其有机电致发光器件 |
| CN108530336A (zh) * | 2018-05-29 | 2018-09-14 | 长春海谱润斯科技有限公司 | 一种并芴化合物及其有机电致发光器件 |
| CN108530469A (zh) * | 2018-05-29 | 2018-09-14 | 长春海谱润斯科技有限公司 | 一种并芴化合物及其有机电致发光器件 |
| CN108727260A (zh) * | 2018-05-29 | 2018-11-02 | 长春海谱润斯科技有限公司 | 一种并芴衍生物及其有机电致发光器件 |
| CN108727252A (zh) * | 2018-05-29 | 2018-11-02 | 长春海谱润斯科技有限公司 | 一种并芴化合物及其有机电致发光器件 |
-
2018
- 2018-04-25 CN CN201810378387.2A patent/CN108358918A/zh not_active Withdrawn
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20100099459A (ko) * | 2009-03-03 | 2010-09-13 | 덕산하이메탈(주) | 비스벤조이미다졸 화합물 및 이를 이용한 유기전기소자, 그단말 |
| WO2012079032A2 (en) * | 2010-12-09 | 2012-06-14 | Trana Discovery, Inc. | Compositions and methods of treating drug-resistant retroviral infections |
| JP2012204794A (ja) * | 2011-03-28 | 2012-10-22 | Sony Corp | 有機電界発光素子および表示装置 |
| CN106467549A (zh) * | 2016-08-03 | 2017-03-01 | 江苏三月光电科技有限公司 | 一种含有苯并咪唑的化合物及其在有机电致发光器件上的应用 |
| CN108358919A (zh) * | 2018-04-25 | 2018-08-03 | 长春海谱润斯科技有限公司 | 一种菲衍生物及其有机电致发光器件 |
| CN108440524A (zh) * | 2018-04-25 | 2018-08-24 | 长春海谱润斯科技有限公司 | 一种三亚苯衍生物及其有机电致发光器件 |
| CN108440525A (zh) * | 2018-04-25 | 2018-08-24 | 长春海谱润斯科技有限公司 | 一种苝衍生物及其有机电致发光器件 |
| CN108530336A (zh) * | 2018-05-29 | 2018-09-14 | 长春海谱润斯科技有限公司 | 一种并芴化合物及其有机电致发光器件 |
| CN108530469A (zh) * | 2018-05-29 | 2018-09-14 | 长春海谱润斯科技有限公司 | 一种并芴化合物及其有机电致发光器件 |
| CN108727260A (zh) * | 2018-05-29 | 2018-11-02 | 长春海谱润斯科技有限公司 | 一种并芴衍生物及其有机电致发光器件 |
| CN108727252A (zh) * | 2018-05-29 | 2018-11-02 | 长春海谱润斯科技有限公司 | 一种并芴化合物及其有机电致发光器件 |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107602440A (zh) * | 2017-10-09 | 2018-01-19 | 长春海谱润斯科技有限公司 | 一种苯并咔唑类有机电致发光材料及其有机发光器件 |
| CN107629062A (zh) * | 2017-10-09 | 2018-01-26 | 长春海谱润斯科技有限公司 | 一种咔唑类衍生物及其有机发光器件 |
| CN107698486A (zh) * | 2017-10-09 | 2018-02-16 | 长春海谱润斯科技有限公司 | 一种苯并咔唑有机化合物及其有机发光器件 |
| CN107698488A (zh) * | 2017-10-09 | 2018-02-16 | 长春海谱润斯科技有限公司 | 一种苯并咔唑类衍生物及其有机发光器件 |
| CN108358919A (zh) * | 2018-04-25 | 2018-08-03 | 长春海谱润斯科技有限公司 | 一种菲衍生物及其有机电致发光器件 |
| CN108440524A (zh) * | 2018-04-25 | 2018-08-24 | 长春海谱润斯科技有限公司 | 一种三亚苯衍生物及其有机电致发光器件 |
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