CN113135935B - 一种多环芳族系化合物及其制备方法和应用 - Google Patents
一种多环芳族系化合物及其制备方法和应用 Download PDFInfo
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- CN113135935B CN113135935B CN202110402169.XA CN202110402169A CN113135935B CN 113135935 B CN113135935 B CN 113135935B CN 202110402169 A CN202110402169 A CN 202110402169A CN 113135935 B CN113135935 B CN 113135935B
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- -1 Polycyclic aromatic compound Chemical class 0.000 title claims abstract description 83
- 238000002360 preparation method Methods 0.000 title claims description 7
- 239000000463 material Substances 0.000 claims abstract description 33
- 239000000126 substance Substances 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims description 109
- 238000003756 stirring Methods 0.000 claims description 54
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 48
- 239000003208 petroleum Substances 0.000 claims description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 42
- 239000010410 layer Substances 0.000 claims description 38
- 238000001816 cooling Methods 0.000 claims description 31
- 239000000243 solution Substances 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 238000012544 monitoring process Methods 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 21
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 238000010438 heat treatment Methods 0.000 claims description 17
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 16
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 16
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 claims description 16
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- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 claims description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
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- 235000010290 biphenyl Nutrition 0.000 claims description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
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- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
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- 125000004062 acenaphthenyl group Chemical group C1(CC2=CC=CC3=CC=CC1=C23)* 0.000 claims 1
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- 125000002346 iodo group Chemical group I* 0.000 description 1
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- 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
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- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
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- 230000000750 progressive effect Effects 0.000 description 1
- 230000001737 promoting 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
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
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- 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
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 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 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-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
Classifications
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- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
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Abstract
本发明公开了一种多环芳族系化合物,结构通式如化学式I或化学式II所示:
Description
技术领域
本发明涉及有机光电材料领域,具体是一种多环芳族系化合物及其制备方法、以及涉及采用该类化合物的有机发光器件。
背景技术
有机电致发光二极管(OLED:Organic Light Emission Diodes)又称为有机电激光显示、有机发光半导体。OLED显示技术具有自发光、高亮度、快响应、宽视角、广色域、柔性化、超薄、超轻、低驱动电压、低功耗、宽温度等显著的优点,是一种发展快、技术更迭迅速的新型显示技术,得到广泛地研究。
OLED显示技术的核心有机发光材料,基于红光材料、绿光材料、蓝光材料三者混合实现全色域。新型发光材料的开发是推动电致发光技术不断进步的源动力,也是有机电致发光产业的研究热点。新型蓝光有机电致发光材料的开发实现器件高发光效率和更优的使用寿命,同时,窄半峰宽、色纯度高的蓝光发光材料是开发蓝光发光材料的重点。
目前,采用多重振动效应(MR效应),利用硼与氮氧等杂原子相反的振动,构建由硼原子与氮氧等杂原子将多个芳香族环缩合形成的多环芳香族化合物,即制备含有硼原子、氮氧杂原子的特殊刚性材料体系。这类荧光分子具有高辐射跃迁速率、窄的半峰宽、高色纯度,但其效率滚降较为严重。
发明内容
有鉴于此,本发明提供了一种多环芳族系化合物及其制备方法和应用,本发明提供的新型结构的多环芳族系化合物,其优势在于用于有机电致发光器件后,使得器件的效率提高,且使用寿命增长。
为了实现上述目的,本发明采用如下技术方案:
一种多环芳族系化合物,其结构通式如化学式I或化学式II所示:
其中,化学式I和化学式II中,Y选自B、N中的任意一种;
X1和X2彼此相同或不同,且各自独立的选自N-R1,C-R2R3、O、S和 Si-R4R5中的任意一种,或者直接键合;
X3和X4其中一个选自O、S、N-Ra、CRbRc和SiRdRe中的任意一种,另外一个为直接键合;
Z各自独立的选自CR6或N;
化学式I中,X5和X6其中一个选自O、S、N-Ra、CRbRc和SiRdRe中的任意一种,另外一个为直接键合。
进一步的,R1-R6彼此相同或不同,并且各自独立地选自氢、氘、经取代或未经取代的碳数为1-30烷基、经取代或未经取代的碳数为6-50芳基、经取代或未经取代的碳数为3-30环烷基、经取代或未经取代的碳数为2-50杂芳基、经取代或未经取代的碳数为1-30烷氧基、经取代或未经取代的碳数为6-30 芳氧基、经取代或未经取代的碳数为1-30烷基胺基、经取代或未经取代的碳数为6-30二芳基氨基、经取代或未经取代的碳数为1-30烷基甲硅烷基、经取代或未经取代的碳数为5-30芳基甲硅烷基、硝基、三氟甲基、氰基和卤素基,并且R1-R6中至少有一个氢可经取代;
R1-R6各自任选地与环A、环B或环C键合以形成取代或未取代脂环族或芳族或杂芳族单环或多环,R2和R3任选地彼此连接以形成取代或未取代脂环族或芳族或杂芳族单环或多环,以及R4和R5任选地彼此连接以形成取代或未取代脂环族或芳族或杂芳族单环或多环;
更进一步的,R1选自经取代的碳数为6-50芳基、经取代或未经取代的碳数为3-30环烷基、经取代或未经取代的碳数为2-50杂芳基或经取代或未经取代的碳数为6-30芳氧基;
R2-R5选自经取代或未经取代的碳数为1-30烷基;
再进一步的,R1选自经取代的碳数为6-50芳基、经取代或未经取代的碳数为2-50杂芳基或经取代或未经取代的碳数为6-30芳氧基;
进一步的,Ra、Rb、Rc、Rd、Re彼此相同或者不同,并且各自独立地选自氢、氘、卤素基、氰基、三氟甲基、经取代或未经取代的C1-C30烷基、经取代或未经取代的C6-C50芳基、经取代或未经取代的C3-C30环烷基、经取代或未经取代的C2-C50杂芳基、经取代或未经取代的C1-C30烷氧基、经取代或未经取代的C6-C30芳氧基、经取代或未经取代的C1-C30烷基硫基、经取代或未经取代的C5-C30芳基硫基、经取代或未经取代的C1-C30烷基胺基、经取代或未经取代的二芳基胺基的芳基为C5-C30的芳基、经取代或未经取代的芳基杂芳基氨基的芳基为碳数为5-30的芳基以及杂芳基为碳数为2-30 的杂芳基,经取代或未经取代的C1-C30烷基甲硅烷基、经取代或未经取代的 C5-C30芳基甲硅烷基、硝基、三氟甲基、氰基和卤素基;
更进一步的,Ra为经取代或未经取代的C6-C50芳基;
更进一步的,Rb-Re均为经取代或未经取代的C1-C30烷基。
进一步的,R6独立的选自氢、氘、卤素基团、氰基、三氟甲基、经取代或未经取代的烷基、经取代或未经取代的芳基、经取代或未经取代的环烷基、经取代或未经取代的杂芳基、经取代或未经取代的烷氧基、经取代或未经取代的芳氧基、经取代或未经取代的烷基硫基、经取代或未经取代的芳基硫基、经取代或未经取代的烷基氨基、经取代或未经取代的二芳基氨基、经取代或未经取代的芳基杂芳基氨基、经取代或未经取代的二杂芳基氨基、经取代或未经取代的烷基甲硅烷基、经取代或未经取代的芳基甲硅烷基;
且,R6任选的与彼此键合或与另外的相邻取代基连接以形成其碳原子任选地被选自N、S和O原子中的一个或更多个杂原子取代的脂环族或芳族或杂芳族单环或多环,所形成的环中的至少一个氢可由氘卤素基、三氟甲基、氰基、芳基、杂芳基、二芳基氨基、二杂芳基氨基、芳基杂芳基氨基、烷基、烷氧基或芳氧基取代,其中上述定义中的芳基为碳数为6-50的芳基,杂芳基为碳数为2-50的杂芳基,烷基为碳数为1-30的烷基,烷氧基为碳数为1-30的烷氧基,芳氧基为碳数为6-30的芳氧基,环烷基为碳数为3-30环烷基;
更进一步的,R6选自氢、卤素基、经取代或未经取代的烷基、经取代或未经取代的芳基、经取代或未经取代的环烷基、经取代或未经取代的芳氧基、经取代或未经取代的烷基硫基、经取代或未经取代的芳基硫基、经取代或未经取代的烷基氨基、经取代或未经取代的二芳基氨基、经取代或未经取代的芳基杂芳基氨基或经取代或未经取代的二杂芳基氨基;
再进一步的,R6选自氢、经取代或未经取代的烷基、经取代或未经取代的芳基、经取代或未经取代的烷基氨基、经取代或未经取代的二芳基氨基、经取代或未经取代的芳氧基、经取代或未经取代的烷基硫基、经取代或未经取代的芳基硫基。
化学式Ⅲ中,D环和E环彼此相同或者不同且各自独立的选自经取代或未取代的芳环、经取代或未取代的杂芳环,经取代或未取代的烷基,且D环和E环中至少有一个为取代或未取代的杂芳环,上述取代的取代基中至少一个氢可由氘、卤素基、氰基、三氟甲基、硝基、甲硅烷基、取代或未取代的芳基、取代或未取代的烷基、取代或未取代的杂芳基取代或未取代的二芳基氨基、取代或未取代的二杂芳基氨基、取代或未取代的芳基杂芳基氨基、取代或未取代烷氧基、取代或未取代芳氧基取代;
上述定义中的芳基为碳数6-50的芳基,杂芳基为碳数为2-50的杂芳基,烷基为碳数为1-30的烷基,烷氧基为碳数为1-30的烷氧基,芳氧基为碳数为 6-30的芳氧基,另外,D环和E环可由O或S或NRf或CRgRh连接或直接键合,Rf、Rg、Rh彼此相同或者不同且各自独立的选自经取代或未取代的芳基、经取代或未取代的杂芳基、经取代或未取代的烷基;
进一步的,D环和E环中至少一个氢经卤素基或氰基或硝基或三氟甲基或甲硅烷基取代;
进一步的,D环和E环可直接键合形成碳数为3-8的含氮杂芳烃环;
进一步的,L为直接键、经取代或未取代碳数为1-12亚烷基、经取代或未取代的碳数为6-30亚芳基、经取代或未取代的碳数为6-20亚杂芳基,n为 0至3的整数,并且当n为2或3时,L彼此相同或者不同;
更进一步的,L为直接键;n为0。
优选地,芳基分别独立选自苯基、萘基、蒽基、菲基、萘并萘基、芘基、基、苝基、茚基、苊基、三亚苯基、二甲基芴基、苯并二甲基芴基、二苯基芴基、苯并二苯基芴基、苯基芴基、螺芴基、苯并螺芴基、联苯基、对三联苯基、间三联苯基中任意一种,但不限于此;/>
优选地,杂芳基分别独立的选自噻吩基、呋喃基、吡咯基、苯并噻吩基、苯并呋喃基、吲哚基、二苯并呋喃基、二苯并噻吩基、吡唑基、苯并吡唑基、苯并咪唑基、咪唑基、取代或未取代咔唑基、苯并萘并呋喃基、苯并萘并噻吩基、苯并咔唑基、二萘并呋喃基、二萘并噻吩基、吡啶基、萘啶基、吖啶基、哒嗪基、吩噻嗪基、苯恶嗪基、吡啶基、联吡啶基、嘧啶基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、吡嗪基、三嗪基、二唑基、三唑基、恶唑基、取代或未噻唑基、恶二唑基、噻二唑基、苯并噻二唑基、嘧啶基、吡嗪基、苯并咪唑基、吲哚基、喹啉基、哒嗪基、酞嗪基、异喹啉基、喹唑啉基、喹喔啉基、菲咯啉基、萘啶基、苯并恶嗪基、苯并噻嗪基、氮杂咔唑基、氮杂二甲基芴基、氮杂二苯基芴基、氮杂苯并二甲基芴基基、氮杂苯并二苯基芴基基、氮杂螺芴基、氮杂苯并螺芴基中任意一个,但不限于此;
优选地,卤素基分别独立选自氟基、氯基、溴基、碘基中任意一种;
优选地,烷基可以为直链或支链的,分别独立选自甲基、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、金刚烷基、异己基、4-甲基己基、5-甲基己基环丙基、环丁基、环戊基、3-甲基环戊基、2,3-二甲基环戊基、环己基、3-甲基环己基、4- 甲基环己基、2,3-二甲基环己基、3,4,5-三甲基环己基、4-叔丁基环己基、环庚基或环辛基中任意一种,但不限于此;
优选地,烷氧基可以为甲氧基、乙氧基、丙氧基、异丁氧基、仲丁氧基、戊氧基、异戊氧基或己氧基中任意一种,但不限于此;
优选地,甲硅烷基可以为三甲基甲硅烷基、三乙基甲硅烷基、三苯基甲硅烷基、三甲氧基甲硅烷基、二甲氧基苯基甲硅烷基、二苯基甲基甲硅烷基、二苯基乙烯基甲硅烷基、甲基环丁基甲硅烷基或二甲基呋喃基甲硅烷基中任意一种,但不限于此;
优选地,芳氧基可以为苯氧基、对甲苯氧基、间甲苯氧基、3,5-二甲基苯氧基、2,4,6-三甲基苯氧基、对叔丁基苯氧基、3-联苯氧基、4-联苯氧基、1- 萘氧基、2-萘氧基、4-甲基-1-萘氧基、5-甲基-2-萘氧基、1-蒽氧基、2-蒽氧基、 9-蒽氧基、1-菲氧基、3-菲氧基或9-菲氧基中任意一种,但不限于此;
本发明中所使用的,R1-R6、Ra-Re以及D环和E环的定义中的术语“经取代的”的表示经选自以下的一个或更多个取代基取代,取代基选自氘、氰基、卤素基、羟基、硝基、三氟甲基、碳数为1-30的烷基、碳数为3-30的环烷基、碳数为6-50芳基、碳数为2-50杂芳基、碳数为1-30烷氧基、碳数为6-30芳氧基、碳数为1-30烷基硫基、碳数为5-30芳基硫基、碳数为1-30烷基胺基、二芳基胺基的芳基为碳数为5-30的芳基、芳基杂芳基氨基的芳基为碳数为 5-30的芳基杂芳基为碳数为2-30的杂芳基,碳数为1-30烷基甲硅烷基、碳数为5-30芳基甲硅烷基;
进一步的,上述的多环芳族系化合物中,选自下述结构式所示化合物中的任意一种:
其中,结构式中的“Me”为甲基,“t-Bu”为叔丁基,“t-Am”为叔戊基,“D”为氘,“AdH”为金刚烷。
需要说明的是,上述化合物的编号与下述实施例中多环芳族系化合物的编号一致,即下述实施例中的多环芳族系化合物编号的化合物对应上述多环芳族系化合物编号化合物以及其结构式。
一种上述多环芳族系化合物的合成工艺,参照下述合成路径合成:
上述式中X1-X6和Z与上述化学式I或II中相同部分表示一致;
具体制备方法为:
在氮气氛围下,将中间体A和无水叔丁基苯置于反应瓶中,在-78℃下,将叔丁基锂的戊烷溶液滴加反应体系中,滴加完毕后,缓慢升温至70~80℃,继续搅拌2~5h,随后降温至-30~-40℃,逐滴滴加三溴化硼,升温至室温,继续搅拌0.5~2h后,向反应体系中滴加N,N-二异丙基乙胺,升温至120~160℃继续反应3~8h,监测反应完毕后,冷却至室温,向反应混合物中滴加饱和碳酸氢钠水溶液,并用乙酸乙酯萃取得有机层,将有机层浓缩并通过柱层析色谱法纯化以得到化学式I或化学式II;
其中,所述中间体A为中间体I-I或中间体II-I;
或;
在氮气氛围下,将中间体B与叔丁醇钠溶于无水甲苯中,室温搅拌10min,将三叔丁基膦、三(二亚苄基丙酮)二钯加入反应体系中,逐渐升温至90-130℃,反应过夜,TCL检测反应完毕后,冷却至室温,搅拌条件下加入蒸馏水,萃取,收集有机相,无水硫酸镁干燥,浓缩后,通过柱层析色谱法纯化得到化学式I或化学式II;
其中,所述中间体B为中间体I-II或中间体II-II。
进一步的,所述所述中间体A、叔丁基锂的戊烷溶液、三溴化硼以及N,N- 二异丙基乙胺的当量比为1:(5-10):(3-6):(8-12);
所述中间体B、叔丁醇钠、三叔丁基膦以及三(二亚苄基丙酮)二钯的当量比为1:(4-6):0.4:0.04。
进一步的,所述柱层析色谱法中洗脱剂为乙酸乙酯和石油醚;所述乙酸乙酯和石油醚的体积比为:1:(10-20)。
本发明的另一个目的在于提供一种上述多环芳族系化合物在发光材料中的应用,发光材料包括上述多环芳族系化合物和荧光主体材料,且荧光主体材料和多环芳族系化合物的重量比为(95:5):(98:2)。
本发明还有一个目的在于提供一种上述多环芳族系化合物在有机电致发光器件中的应用,有机电致发光器件包括第一电极,第二电极,以及设置在所述第一电极和所述第二电极之间的发光层,发光层至少设置有一层,且至少一个层包括上述的发光材料。
进一步的,第一电极和第二电极之间设置包括空穴注入层、空穴传输层、发光辅助层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层的至少一层或多层。
进一步的,第一电极作为阳极,阳极优选包含具有高逸出功的材料。例如氧化锡铟(ITO)或氧化铟锌(IZO)。由于在水和/或空气存在下本发明器件的寿命会缩短,所以所述器件被适当地(取决于应用)结构化、提供接点并最后密封。
进一步的,空穴传输材料是能够接收来自阳极或空穴注入层的空穴并将空穴传输至发光层的材料,并且具有高空穴迁移率的材料,其具体实例包括基于芳基胺的有机材料、导电聚合物、同时具有共轭部分和非共轭部分的嵌段共聚物等,但不限于此。
进一步的,电子阻挡层可以设置在空穴传输层与发光层之间,作为电子阻挡层,可以使用本领域中已知的材料,例如基于芳基胺的有机材料。
进一步的,空穴阻挡层材料,可以使用现有技术中公知的具有空穴阻挡作用的化合物,例如,浴铜灵(BCP)等菲咯啉衍生物、噁唑衍生物、三唑衍生物、三嗪衍生物等,但不限于此。
进一步的,电子传输层可以起到促进电子传输的作用。可以使用现有技术中公知的具有电子传输作用的化合物,例如,8-羟基喹啉的Al配合物;包含Alq3的配合物;有机自由基化合物;羟基黄酮-金属配合物等。
进一步的,电子注入层可以起到促进电子注入的作用。具有传输电子的能力,防止发光层中产生的激子迁移至空穴注入层。本发明中使用的电子注入材料包括芴酮、蒽醌二甲烷、联苯醌、噻喃二氧化物、唑、二唑、三唑、咪唑、苝四羧酸、亚芴基甲烷、蒽酮等及其衍生物,金属配合物,含氮五元环衍生物等,但不限于此。
进一步的,第二电极作为阴极,通常优选具有小功函数的材料使得电子顺利注入有机材料层。例如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅,或其合金。
经由上述的技术方案可知,与现有技术相比,本发明具有如下有益效果:
本发明实施例提供的多环芳族系化合物为扁平型的高共轭电子分布系统,让分子间有效并且有次序地堆栈,从而在一定的电场下发挥最佳的载子传输与迁移。同时将一些刚性的并具有高立体阻碍性的分子基团合成于分子结构中,使分子与分子间作用减弱,避免能量转换与高浓度下的荧光淬熄,使得半峰宽变窄,器件寿命合效率得到大大提高。
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
本发明实施例提供一种多环芳族系化合物(记为化合物1)及其合成工艺,具体地,参照下述合成路径合成得到化合物1:
具体操作如下:(1)在氮气保护下,将反应物1-1(120mmol)、叔丁醇钠 (220mmol)加入1000ml的三口瓶中,并用500ml的干燥甲苯溶液溶解,室温搅拌10min后,室温条件下加入反应物1-2(120mmol)、三叔丁基膦(12mmol)、三(二亚苄基丙酮)二钯(2mmol),随后缓慢升高反应温度至90℃,继续反应 12h,利用TLC监测反应,待反应结束后,冷却至室温,搅拌条件下加入适量蒸馏水,分液后保留有机相。无水硫酸镁干燥后,收集滤液,将滤液利用硅藻土过滤,除去催化剂,将所得滤液利用旋转式蒸发仪旋干后,溶解在石油醚/乙醇中,进行重结晶,过滤,将滤饼用石油醚多次淋洗,放入60℃烘箱干燥5h,得到中间体1-3(36.2g,产率:90.1%,Ms:334.91)。
(2)在氮气保护下,将中间体1-3(110mmol)、叔丁醇钠(220mmol)加入 1000ml的三口瓶中,并用500ml的干燥甲苯溶液溶解,室温搅拌10min后,室温条件下加入反应物1-4(110mmol)、三叔丁基膦(11mmol)、三(二亚苄基丙酮)二钯(2mmol),随后缓慢升高反应温度至90℃,继续反应12h。利用TLC 监测反应,待反应结束后,冷却至室温,搅拌条件下加入适量蒸馏水,分液后保留有机相。无水硫酸镁干燥后,收集滤液,将滤液利用硅藻土过滤,除去催化剂,将所得滤液利用旋转式蒸发仪旋干后,溶解在石油醚/乙醇中,进行重结晶,过滤,将滤饼用石油醚多次淋洗,放入60℃烘箱干燥7h,得到中间体1-5(48.5g,产率:85.3%,Ms:516.93)。
(3)在氮气保护下,将反应物1-6(85mmol)、叔丁醇钠(170mmol)加入 500ml的三口瓶中,并用500ml的干燥甲苯溶液溶解,室温搅拌10min后,室温条件下加入中间体1-5(85mmol)、三叔丁基膦(8.5mmol)、三(二亚苄基丙酮)二钯(1.7mmol),随后缓慢升高反应温度至90℃,继续反应12h,利用TLC 监测反应,待反应结束后,冷却至室温,搅拌条件下加入适量蒸馏水,分液后保留有机相,无水硫酸镁干燥后,收集滤液,将滤液利用硅藻土过滤,除去催化剂,将所得滤液利用旋转式蒸发仪旋干后,溶解在石油醚/乙醇中,进行重结晶,过滤,将滤饼用石油醚多次淋洗,放入60℃烘箱干燥7h,得到中间体1-7(44.5g,产率:86.5%,Ms:605.55)。
(4)在氮气保护下,将中间体1-8(70mmol)、叔丁醇钠(140mmol)加入 1000ml的三口瓶中,并用500ml的干燥甲苯溶液溶解,室温搅拌10min后,室温条件下加入反应物1-7(70mmol)、三叔丁基膦(7mmol)、三(二亚苄基丙酮) 二钯(1.4mmol),随后缓慢升高反应温度至90℃,继续反应12h,利用TLC监测反应,待反应结束后,冷却至室温,搅拌条件下加入适量蒸馏水,分液后保留有机相,无水硫酸镁干燥后,收集滤液,将滤液利用硅藻土过滤,除去催化剂,将所得滤液利用旋转式蒸发仪旋干后,溶解在石油醚/乙醇中,进行重结晶,过滤,将滤饼用石油醚多次淋洗,放入60℃烘箱干燥7h,得到中间体1-9(49.8g,产率:89.6%,Ms:794.40)。
(5)在氮气氛围下,将中间体1-9(50mmol)和无水叔丁基苯置于反应瓶中,置换氮气,在-78℃条件下,将叔丁基锂的戊烷溶液(250mmol)滴加反应体系中,滴加完毕后,缓慢升温至65℃,继续搅拌3h,随后降温至-30℃,逐滴滴加三溴化硼(250mmol),升温至室温,继续搅拌1h后,向反应体系中滴加 N,N-二异丙基乙胺(500mmol)。升温至145℃继续反应4h,监测反应完毕后,冷却至室温,向反应混合物中滴加饱和碳酸氢钠水溶液,并用乙酸乙酯萃取。将有机层浓缩并通过柱层析色谱法(洗脱剂:V(乙酸乙酯):V(石油醚) =1:20)纯化以得到化合物1(8.2g,产率:21.4%)。
对所得化合物1进行检测分析,结果如下:
质谱测试:理论值为767.74;测试值为767.14。
元素分析:
理论值为:C,78.22;H,4.07;B,1.41;F,2.47;N,5.47;S,8.35
测试值为:C,78.01;H,4.13;B,1.39;F,2.52;N,5.53;S,8.32。
实施例2:
本发明实施例提供一种多环芳族系化合物(记为化合物6)及其合成工艺,具体地,参照下述合成路径合成得到化合物6:
具体操作如下:(1)在氮气保护下,将反应物6-1(120mmol)、叔丁醇钠 (220mmol)加入1000ml的三口瓶中,并用500ml的干燥甲苯溶液溶解,室温搅拌10min后,室温条件下加入反应物6-2(120mmol)、三叔丁基膦(12mmol)、三(二亚苄基丙酮)二钯(2mmol),随后缓慢升高反应温度至90℃,继续反应 12h,利用TLC监测反应,待反应结束后,冷却至室温,搅拌条件下加入适量蒸馏水,分液后保留有机相,无水硫酸镁干燥后,收集滤液,将滤液利用硅藻土过滤,除去催化剂,将所得滤液利用旋转式蒸发仪旋干后,溶解在石油醚/乙醇中,进行重结晶,过滤,将滤饼用石油醚多次淋洗,放入60℃烘箱干燥5h,得到中间体6-3(34.0g,产率:89.4%,Ms:317.01)。
(2)在氮气保护下,将中间体6-3(110mmol)、叔丁醇钠(220mmol)加入 1000ml的三口瓶中,并用500ml的干燥甲苯溶液溶解,室温搅拌10min后,室温条件下加入反应物6-4(110mmol)、三叔丁基膦(11mmol)、三(二亚苄基丙酮)二钯(2mmol),随后缓慢升高反应温度至90℃,继续反应12h,利用TLC 监测反应,待反应结束后,冷却至室温,搅拌条件下加入适量蒸馏水,分液后保留有机相。无水硫酸镁干燥后,收集滤液,将滤液利用硅藻土过滤,除去催化剂,将所得滤液利用旋转式蒸发仪旋干后,溶解在石油醚/乙醇中,进行重结晶,过滤,将滤饼用石油醚多次淋洗,放入60℃烘箱干燥7h,得到中间体6-5(45.0g,产率:84.6%,Ms:483.18)。
(3)在氮气保护下,将反应物6-6(85mmol)、叔丁醇钠(170mmol)加入 500ml的三口瓶中,并用500ml的干燥甲苯溶液溶解,室温搅拌10min后,室温条件下加入中间体6-5(85mmol)、三叔丁基膦(8.5mmol)、三(二亚苄基丙酮)二钯(1.7mmol),随后缓慢升高反应温度至90℃,继续反应12h,利用TLC 监测反应,待反应结束后,冷却至室温,搅拌条件下加入适量蒸馏水,分液后保留有机相。无水硫酸镁干燥后,收集滤液,将滤液利用硅藻土过滤,除去催化剂,将所得滤液利用旋转式蒸发仪旋干后,溶解在石油醚/乙醇中,进行重结晶,过滤,将滤饼用石油醚多次淋洗,放入60℃烘箱干燥7h,得到中间体6-7(42.0g,产率:86.5%,Ms:571.49)。
(4)在氮气保护下,将中间体6-8(70mmol)、叔丁醇钠(140mmol)加入 1000ml的三口瓶中,并用500ml的干燥甲苯溶液溶解,室温搅拌10min后,室温条件下加入反应物6-7(70mmol)、三叔丁基膦(7mmol)、三(二亚苄基丙酮) 二钯(1.4mmol),随后缓慢升高反应温度至90℃,继续反应12h,利用TLC监测反应,待反应结束后,冷却至室温,搅拌条件下加入适量蒸馏水,分液后保留有机相。无水硫酸镁干燥后,收集滤液,将滤液利用硅藻土过滤,除去催化剂,将所得滤液利用旋转式蒸发仪旋干后,溶解在石油醚/乙醇中,进行重结晶,过滤,将滤饼用石油醚多次淋洗,放入60℃烘箱干燥7h,得到中间体6-9(42.8g,产率:80.6%,Ms:760.34)。
(5)在氮气氛围下,将中间体6-9(50mmol)和无水叔丁基苯置于反应瓶中,置换氮气,在-78℃条件下,将叔丁基锂的戊烷溶液(250mmol)滴加反应体系中。滴加完毕后,缓慢升温至65℃,继续搅拌3h,随后降温至-30℃,逐滴滴加三溴化硼(250mmol),升温至室温,继续搅拌1h后,向反应体系中滴加 N,N-二异丙基乙胺(500mmol),升温至145℃继续反应4h,监测反应完毕后,冷却至室温,向反应混合物中滴加饱和碳酸氢钠水溶液,并用乙酸乙酯萃取。将有机层浓缩并通过柱层析色谱法(洗脱剂:V(乙酸乙酯):V(石油醚) =1:20)纯化以得到化合物6(7.1g,产率:19.3%)。
对所得化合物6进行检测分析,结果如下:
质谱测试:理论值为733.68;测试值为733.43。
元素分析:
理论值为:C,81.85;H,4.40;B,1.47;N,5.73;O,2.18;S,4.37
测试值为:C,81.72;H,4.51;B,1.37;N,5.84;O,2.10;S,4.37。
实施例3:
本发明实施例提供一种多环芳族系化合物(记为化合物36)及其合成工艺,具体地,参照下述合成路径合成得到化合物36:
具体操作如下:(1)在氮气保护下,将反应物36-1(120mmol)、叔丁醇钠(220mmol)加入1000ml的三口瓶中,并用400ml的干燥甲苯溶液溶解,室温搅拌10min后,室温条件下加入反应物36-2(120mmol)、三叔丁基膦 (12mmol)、三(二亚苄基丙酮)二钯(2mmol),随后缓慢升高反应温度至90℃,继续反应12h。利用TLC监测反应,待反应结束后,冷却至室温,搅拌条件下加入适量蒸馏水,分液后保留有机相。无水硫酸镁干燥后,收集滤液,将滤液利用硅藻土过滤,除去催化剂,将所得滤液利用旋转式蒸发仪旋干后,溶解在石油醚/乙醇中,进行重结晶,过滤,将滤饼用石油醚多次淋洗,放入 60℃烘箱干燥5h,得到中间体36-3(43.4g,产率:88.7%,Ms:407.57)。
(2)在氮气保护下,将中间体36-3(110mmol)、叔丁醇钠(220mmol)加入 1000ml的三口瓶中,并用500ml的干燥甲苯溶液溶解,室温搅拌10min后,室温条件下加入反应物36-4(110mmol)、三叔丁基膦(11mmol)、三(二亚苄基丙酮)二钯(2mmol),随后缓慢升高反应温度至90℃,继续反应12h。利用TLC 监测反应,待反应结束后,冷却至室温,搅拌条件下加入适量蒸馏水,分液后保留有机相,无水硫酸镁干燥后,收集滤液,将滤液利用硅藻土过滤,除去催化剂,将所得滤液利用旋转式蒸发仪旋干后,溶解在石油醚/乙醇中,进行重结晶,过滤,将滤饼用石油醚多次淋洗,放入60℃烘箱干燥7h,得到中间体36-5(48.2g,产率:87.3%,Ms:502.07)。
(3)在氮气保护下,将反应物36-6(85mmol)、叔丁醇钠(170mmol)加入 500ml的三口瓶中,并用500ml的干燥甲苯溶液溶解,室温搅拌10min后,室温条件下加入中间体36-5(85mmol)、三叔丁基膦(8.5mmol)、三(二亚苄基丙酮)二钯(1.7mmol),随后缓慢升高反应温度至90℃,继续反应12h。利用TLC 监测反应,待反应结束后,冷却至室温,搅拌条件下加入适量蒸馏水,分液后保留有机相。无水硫酸镁干燥后,收集滤液,将滤液利用硅藻土过滤,除去催化剂,将所得滤液利用旋转式蒸发仪旋干后,溶解在石油醚/乙醇中,进行重结晶,过滤,将滤饼用石油醚多次淋洗,放入60℃烘箱干燥7h,得到中间体36-7(40.3g,产率:84.9%,Ms:558.73)。
(4)在氮气保护下,将中间体36-8(70mmol)、叔丁醇钠(140mmol)加入 1000ml的三口瓶中,并用500ml的干燥甲苯溶液溶解,室温搅拌10min后,室温条件下加入反应物36-7(70mmol)、三叔丁基膦(7mmol)、三(二亚苄基丙酮)二钯(1.4mmol),随后缓慢升高反应温度至90℃,继续反应12h。利用TLC 监测反应,待反应结束后,冷却至室温,搅拌条件下加入适量蒸馏水,分液后保留有机相。无水硫酸镁干燥后,收集滤液,将滤液利用硅藻土过滤,除去催化剂,将所得滤液利用旋转式蒸发仪旋干后,溶解在石油醚/乙醇中,进行重结晶,过滤,将滤饼用石油醚多次淋洗,放入60℃烘箱干燥7h,得到中间体36-9(40.1g,产率:82.6%,Ms:703.72)。
(5)在氮气保护下,将中间体36-10(60mmol)、叔丁醇钠(120mmol)加入 1000ml的三口瓶中,并用500ml的干燥甲苯溶液溶解,室温搅拌10min后,室温条件下加入反应物36-9(60mmol)、三叔丁基膦(6mmol)、三(二亚苄基丙酮)二钯(1.2mmol),随后缓慢升高反应温度至90℃,继续反应12h,利用TLC 监测反应,待反应结束后,冷却至室温,搅拌条件下加入适量蒸馏水,分液后保留有机相。无水硫酸镁干燥后,收集滤液,将滤液利用硅藻土过滤,除去催化剂,将所得滤液利用旋转式蒸发仪旋干后,溶解在石油醚/乙醇中,进行重结晶,过滤,将滤饼用石油醚多次淋洗,放入60℃烘箱干燥7h,得到中间体36-11(43.7g,产率:81.6%,Ms:892.57)。
(6)在氮气氛围下,将中间体36-11(50mmol)和无水叔丁基苯置于反应瓶中,置换氮气,在-78℃条件下,将叔丁基锂的戊烷溶液(250mmol)滴加反应体系中。滴加完毕后,缓慢升温至65℃,继续搅拌3h,随后降温至-30℃,逐滴滴加三溴化硼(250mmol),升温至室温,继续搅拌1h后,向反应体系中滴加N,N-二异丙基乙胺(500mmol),升温至145℃继续反应4h,监测反应完毕后,冷却至室温,向反应混合物中滴加饱和碳酸氢钠水溶液,并用乙酸乙酯萃取。将有机层浓缩并通过柱层析色谱法(洗脱剂:V(乙酸乙酯):V(石油醚) =1:20)纯化以得到化合物36(7.5g,产率:17.4%)。
对所得化合物36进行检测分析,结果如下:
质谱测试:理论值为865.91;测试值为865.63。
元素分析:
理论值为:C,81.84;H,4.66;B,1.25;N,4.85;S,7.41
测试值为:C,81.63;H,4.63;B,1.36;N,4.92;S,7.44。
实施例4:
本发明实施例提供一种多环芳族系化合物(记为化合物46)及其合成工艺,具体地,参照下述合成路径合成得到化合物46:
具体操作如下:(1)在氮气保护下,将反应物46-1(120mmol)、叔丁醇钠(220mmol)加入1000ml的三口瓶中,并用500ml的干燥甲苯溶液溶解,室温搅拌10min后,室温条件下加入反应物46-2(120mmol)、三叔丁基膦 (12mmol)、三(二亚苄基丙酮)二钯(2mmol),随后缓慢升高反应温度至90℃,继续反应12h,利用TLC监测反应,待反应结束后,冷却至室温,搅拌条件下加入适量蒸馏水,分液后保留有机相,无水硫酸镁干燥后,收集滤液,将滤液利用硅藻土过滤,除去催化剂,将所得滤液利用旋转式蒸发仪旋干后,溶解在石油醚/乙醇中,进行重结晶,过滤,将滤饼用石油醚多次淋洗,放入 60℃烘箱干燥5h,得到中间体46-3(27.8g,产率:89.3%,Ms:259.30)。
(2)在氮气保护下,将中间体46-3(110mmol)、叔丁醇钠(220mmol)加入 1000ml的三口瓶中,并用500ml的干燥甲苯溶液溶解,室温搅拌10min后,室温条件下加入反应物46-4(110mmol)、三叔丁基膦(11mmol)、三(二亚苄基丙酮)二钯(2mmol),随后缓慢升高反应温度至90℃,继续反应12h,利用TLC 监测反应,待反应结束后,冷却至室温,搅拌条件下加入适量蒸馏水,分液后保留有机相,无水硫酸镁干燥后,收集滤液,将滤液利用硅藻土过滤,除去催化剂,将所得滤液利用旋转式蒸发仪旋干后,溶解在石油醚/乙醇中,进行重结晶,过滤,将滤饼用石油醚多次淋洗,放入60℃烘箱干燥7h,得到中间体46-5(37.1g,产率:91.2%,Ms:369.84)。
(3)在氮气保护下,将反应物46-6(90mmol)、叔丁醇钠(180mmol)加入 1000ml的三口瓶中,并用500ml的干燥甲苯溶液溶解,室温搅拌10min后,室温条件下加入中间体46-5(90mmol)、三叔丁基膦(9mmol)、三(二亚苄基丙酮)二钯(1.8mmol),随后缓慢升高反应温度至90℃,继续反应12h,利用TLC 监测反应,待反应结束后,冷却至室温,搅拌条件下加入适量蒸馏水,分液后保留有机相。无水硫酸镁干燥后,收集滤液,将滤液利用硅藻土过滤,除去催化剂,将所得滤液利用旋转式蒸发仪旋干后,溶解在石油醚/乙醇中,进行重结晶,过滤,将滤饼用石油醚多次淋洗,放入60℃烘箱干燥7h,得到中间体46-7(32.1g,产率:83.5%,Ms:426.51)。
(4)在氮气保护下,将中间体46-8(120mmol)、叔丁醇钠(220mmol)加入 1000ml的三口瓶中,并用500ml的干燥甲苯溶液溶解,室温搅拌10min后,室温条件下加入反应物46-9(120mmol)、三叔丁基膦(12mmol)、三(二亚苄基丙酮)二钯(2mmol),随后缓慢升高反应温度至90℃,继续反应12h,利用TLC 监测反应,待反应结束后,冷却至室温,搅拌条件下加入适量蒸馏水,分液后保留有机相,无水硫酸镁干燥后,收集滤液,将滤液利用硅藻土过滤,除去催化剂,将所得滤液利用旋转式蒸发仪旋干后,溶解在石油醚/乙醇中,进行重结晶,过滤,将滤饼用石油醚多次淋洗,放入60℃烘箱干燥7h,得到中间体46-10(33.7g,产率:88.7%,Ms:317.01)。
(5)在氮气保护下,将中间体46-10(110mmol)、叔丁醇钠(120mmol)加入1000ml的三口瓶中,并用500ml的干燥甲苯溶液溶解,室温搅拌10min后,室温条件下加入反应物46-11(110mmol)、三叔丁基膦(11mmol)、三(二亚苄基丙酮)二钯(2mmol),随后缓慢升高反应温度至90℃,继续反应12h,利用TLC 监测反应,待反应结束后,冷却至室温,搅拌条件下加入适量蒸馏水,分液后保留有机相。无水硫酸镁干燥后,收集滤液,将滤液利用硅藻土过滤,除去催化剂,将所得滤液利用旋转式蒸发仪旋干后,溶解在石油醚/乙醇中,进行重结晶,过滤,将滤饼用石油醚多次淋洗,放入60℃烘箱干燥7h,得到中间体46-12(45.1g,产率:84.8%,Ms:483.18)。
(6)在氮气保护下,将中间体46-13(90mmol)、叔丁醇钠(180mmol)加入 1000ml的三口瓶中,并用500ml的干燥甲苯溶液溶解,室温搅拌10min后,室温条件下加入反应物46-12(90mmol)、三叔丁基膦(9mmol)、三(二亚苄基丙酮)二钯(1.8mmol),随后缓慢升高反应温度至90℃,继续反应12h。利用TLC 监测反应,待反应结束后,冷却至室温,搅拌条件下加入适量蒸馏水,分液后保留有机相,无水硫酸镁干燥后,收集滤液,将滤液利用硅藻土过滤,除去催化剂,将所得滤液利用旋转式蒸发仪旋干后,溶解在石油醚/乙醇中,进行重结晶,过滤,将滤饼用石油醚多次淋洗,放入60℃烘箱干燥7h,得到中间体46-14(61.2g,产率:82.1%,Ms:828.78)。
(7)在氮气保护下,将中间体46-15(60mmol)、叔丁醇钠(120mmol)加入 1000ml的三口瓶中,并用500ml的干燥甲苯溶液溶解,室温搅拌10min后,室温条件下加入反应物46-14(60mmol)、三叔丁基膦(6mmol)、三(二亚苄基丙酮)二钯(1.2mmol),随后缓慢升高反应温度至90℃,继续反应12h,利用TLC 监测反应,待反应结束后,冷却至室温,搅拌条件下加入适量蒸馏水,分液后保留有机相。无水硫酸镁干燥后,收集滤液,将滤液利用硅藻土过滤,除去催化剂,将所得滤液利用旋转式蒸发仪旋干后,溶解在石油醚/乙醇中,进行重结晶,过滤,将滤饼用石油醚多次淋洗,放入60℃烘箱干燥7h,得到中间体46-16(50.0g,产率:78.6%,Ms:1017.63)。
(8)在氮气氛围下,将中间体46-16(50mmol)和无水叔丁基苯置于反应瓶中,置换氮气,在-78℃条件下,将叔丁基锂的戊烷溶液(250mmol)滴加反应体系中,滴加完毕后,缓慢升温至65℃,继续搅拌3h,随后降温至-30℃,逐滴滴加三溴化硼(250mmol),升温至室温,继续搅拌1h后,向反应体系中滴加N,N-二异丙基乙胺(500mmol)。升温至145℃继续反应4h,监测反应完毕后,冷却至室温,向反应混合物中滴加饱和碳酸氢钠水溶液,并用乙酸乙酯萃取,将有机层浓缩并通过柱层析色谱法(洗脱剂:V(乙酸乙酯):V(石油醚) =1:20)纯化以得到化合物46(8.3g,产率:16.8%)。
对所得化合物46进行检测分析,结果如下:
质谱测试:理论值为990.97;测试值为991.03。
元素分析:
理论值为:C,82.42;H,4.37;B,1.09;N,5.65;O,3.23;S,3.24
测试值为:C,82.30;H,4.33;B,1.03;N,5.71;O,3.35;S,3.28。
实施例5-实施例25
参照实施例1至6的合成方法制备得到化合物98,103,3,8,14,23, 26,33,45,52,55,60,70,83,89,92,96,101,105,113,120,对应化合物的质谱和分子式列于下表:
应用例1
制备有机电致发光器件:将具有15Ψ/cm2的片电阻值的ITO玻璃基板切成50mm×50mm×0.7mm大小作为阳极;将切开的基板分别在丙酮、异丙醇和纯水中用超声波清洗15min;并UV臭氧清洗30min,送到蒸镀机里。
在真空度为650×10-7Pa和沉积速度为0.1-0.3nm/s的条件下,首先蒸镀厚度为150nm的ITO玻璃基板作为阳极,蒸镀厚度为20nm的HATCH作为空穴注入层,紧接着蒸镀40nm的NPB作为空穴传输层。
在相同的真空沉积条件下,同时蒸镀厚度为30nm主体材料和掺杂物质作为发光层。其中,荧光主体材料为ADN,实施例1制备得到的化合物1作为掺杂剂,按照98:2重量比混合蒸镀。
在相同的真空沉积条件下,在发光层的上表面依次蒸镀双(2-甲基-8-羟基喹啉)-4-(苯基苯酚)铝(BAlq)作为空穴阻挡层和Alq3(30nm)作为电子传输层,蒸镀电子注入层Liq(1nm)、蒸镀阴极Al(150nm)制备得到有机电致发光器件。
对得到的器件的性能发光特性测试,测量采用KEITHLEY2400型源测量单元,CS-2000分光辐射亮度计,以评价驱动电压,发光效率和器件寿命。
上述原料的化学结构式如下所示:
应用例2-25
参照应用例1的制备方法制备有机电致发光器件,区别在于将应用例1 中的实施例1的化合物1替换为实施例2-25对应的化合物。
对比例1:
按照上述制备方法制备有机电致发光器件,其中发光层的掺杂材料化合物替换为下述化合物(标记为对比化合物1):
实验例:
用公知的驱动电路将阳极和阴极连接起来,测量上述制备得到的有机电致发光器件的电流效率以及器件的寿命,检测结果参见下表(亮度值为 1000cd/m2);
根据上表可知,使用本发明提供的化合物作为发光层中的掺杂材料所制备的有机电致发光器件与使用比较化合物1作为掺杂材料所制备的有机电致发光器件相比,发光效率大幅提高,寿命提高20-60h。
掺杂对比化合物1的效率滚降与掺杂本专利发明化合物不同,本专利发明化合物效率滚降更低,并且具有优异的色纯度。
本发明化合物与ADN之间具有更好的能量传递效果,得到的蓝光色度值更加纯净。
以上所述仅为本发明的优选实施例而已,并不用于限制本发明,对于本领域的技术人员来说,本发明可以有各种更改和变化。凡在本发明的精神和原则之内,所作的任何修改、等同替换、改进等,均应包含在本发明的保护范围之内。
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。对于实施例公开的装置而言,由于其与实施例公开的方法相对应,所以描述的比较简单,相关之处参见方法部分说明即可。
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 (7)
1.一种多环芳族系化合物,其特征在于,结构通式如化学式II所示:
其中,所述化学式II中,Y选自B;
X1和X2各自独立的选自N-R1;
X3为直接键合;X4选自O、S、N-Ra、CRbRc或SiRdRe;
Z选自CR6;
所述R1选自经取代或未经取代的芳基、经取代或未经取代的杂芳基;
所述Ra-Re各自独立的选自氘、未取代的C1-C30烷基、未取代的芳基;
R6选自氢、氘、未取代的烷基、未取代的芳基或如化学式III所示的基团,且,所述R6任选地与彼此键合或与其相邻取代基连接;
R6中至少有一个为如化学式III所示的基团;
所述D环和E环各自独立的选自经取代或未取代的芳基、经取代或未取代的杂芳基,
且D环和E环中至少有一个为经取代或未取代的杂芳基,
所述L选自直接键;
所述n为0-3的整数;
所述术语“经取代”表示经选自以下的一个或更多个取代基取代,取代基选自氘、氰基、卤素基、碳数为1-30的烷基;
所述芳基分别独立选自苯基、萘基、蒽基、菲基、萘并萘基、芘基、苝基、茚基、苊基、三亚苯基、二甲基芴基、苯并二甲基芴基、二苯基芴基、苯并二苯基芴基、苯基芴基、螺芴基、苯并螺芴基、联苯基、对三联苯基、间三联苯基中任意一种;
所述杂芳基分别独立的选自噻吩基、呋喃基、吡咯基、苯并噻吩基、苯并呋喃基、吲哚基、二苯并呋喃基、二苯并噻吩基、吡唑基、苯并吡唑基、苯并咪唑基、咪唑基、咔唑基、苯并萘并呋喃基、苯并萘并噻吩基、苯并咔唑基、二萘并呋喃基、二萘并噻吩基、吡啶基、萘啶基、吖啶基、哒嗪基、吩噻嗪基、苯恶嗪基、联吡啶基、嘧啶基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、吡嗪基、三嗪基、二唑基、三唑基、恶唑基、噻唑基、恶二唑基、噻二唑基、苯并噻二唑基、喹啉基、酞嗪基、异喹啉基、喹唑啉基、喹喔啉基、菲咯啉基、苯并恶嗪基、苯并噻嗪基、氮杂咔唑基、氮杂二甲基芴基、氮杂二苯基芴基、氮杂苯并二甲基芴基、氮杂苯并二苯基芴基、氮杂螺芴基、氮杂苯并螺芴基中任意一个。
3.一种如权利要求1所述的多环芳族系化合物的制备方法,其特征在于,所述化学式II合成路径如下:
具体制备方法为:
在氮气氛围下,将中间体A和无水叔丁基苯置于反应瓶中,在-78℃下,将叔丁基锂的戊烷溶液滴加反应体系中,滴加完毕后,缓慢升温至70~80℃,继续搅拌2~5h,随后降温至-30~-40℃,逐滴滴加三溴化硼,升温至室温,继续搅拌0.5~2h后,向反应体系中滴加N,N-二异丙基乙胺,升温至120~160℃继续反应3~8h,监测反应完毕后,冷却至室温,向反应混合物中滴加饱和碳酸氢钠水溶液,并用乙酸乙酯萃取得有机层,将有机层浓缩并通过柱层析色谱法纯化以得到化学式II;
其中,所述中间体A为中间体II-I。
4.根据权利要求3所述的一种多环芳族系化合物的制备方法,其特征在于,所述中间体A、叔丁基锂的戊烷溶液、三溴化硼以及N,N-二异丙基乙胺的当量比为1:(5-10):(3-6):(8-12)。
5.根据权利要求4所述的一种多环芳族系化合物的制备方法,其特征在于,所述柱层析色谱法中洗脱剂为乙酸乙酯和石油醚;所述乙酸乙酯和石油醚的体积比为:1:(10-20)。
6.一种如权利要求1所述多环芳族系化合物在制备发光材料中的应用,其特征在于,所述发光材料包括权利要求1所述多环芳族系化合物和荧光主体材料,且所述荧光主体材料与所述多环芳族系化合物的重量比为95:5至98:2。
7.一种如权利要求1所述多环芳族系化合物在制备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包括第一电极,第二电极,以及设置在所述第一电极和所述第二电极之间的发光层,所述发光层至少设置有一层,且至少一个层包括权利要求1所述的化合物。
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