CN111793002A - 一种有机发光化合物及其制备方法和有机电致发光器件 - Google Patents
一种有机发光化合物及其制备方法和有机电致发光器件 Download PDFInfo
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- CN111793002A CN111793002A CN202010715743.2A CN202010715743A CN111793002A CN 111793002 A CN111793002 A CN 111793002A CN 202010715743 A CN202010715743 A CN 202010715743A CN 111793002 A CN111793002 A CN 111793002A
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- 239000012074 organic phase Substances 0.000 claims description 21
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 18
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
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- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 claims description 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 9
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 9
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 7
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- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 6
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- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 4
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
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- CRXBTDWNHVBEIC-UHFFFAOYSA-N 1,2-dimethyl-9h-fluorene Chemical compound C1=CC=C2CC3=C(C)C(C)=CC=C3C2=C1 CRXBTDWNHVBEIC-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
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- 125000003944 tolyl group Chemical group 0.000 claims description 3
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- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 2
- KKHFRAFPESRGGD-UHFFFAOYSA-N 1,3-dimethyl-7-[3-(n-methylanilino)propyl]purine-2,6-dione Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCCN(C)C1=CC=CC=C1 KKHFRAFPESRGGD-UHFFFAOYSA-N 0.000 description 2
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
- AVYVHIKSFXVDBG-UHFFFAOYSA-N N-benzyl-N-hydroxy-2,2-dimethylbutanamide Chemical compound C(C1=CC=CC=C1)N(C(C(CC)(C)C)=O)O AVYVHIKSFXVDBG-UHFFFAOYSA-N 0.000 description 2
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- JFARSZKBZGPJGR-UHFFFAOYSA-N 2-(6-azaspiro[2.5]octan-6-yl)-N-[2-(4-fluoro-4-methylpiperidin-1-yl)-6-methylpyrimidin-4-yl]-4-(2-hydroxyethylsulfonylamino)benzamide Chemical compound FC1(CCN(CC1)C1=NC(=CC(=N1)NC(C1=C(C=C(C=C1)NS(=O)(=O)CCO)N1CCC2(CC2)CC1)=O)C)C JFARSZKBZGPJGR-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
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- 150000004982 aromatic amines Chemical class 0.000 description 1
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- 230000004888 barrier function Effects 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
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- 125000005843 halogen group Chemical group 0.000 description 1
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- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
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- 125000002950 monocyclic group Chemical group 0.000 description 1
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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 1
- 239000001301 oxygen Chemical group 0.000 description 1
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- 238000005215 recombination Methods 0.000 description 1
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- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Chemical group 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/94—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
- C07D311/90—Xanthenes with hydrocarbon radicals, substituted by amino radicals, directly attached in position 9
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
- C07D335/20—Thioxanthenes with hydrocarbon radicals, substituted by amino radicals, directly attached in position 9
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D345/00—Heterocyclic compounds containing rings having selenium or tellurium atoms as the only ring hetero atoms
-
- 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
- C07D407/02—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 two hetero rings
- C07D407/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
本发明提供了一种有机发光化合物,具有式Ⅰ所示结构。本发明通过在萘环上的不同活性位点与母核和侧链基团连接,极大拓展了结构设计方向,可以设计并合成出具有更为精细差异空间构象的分子结构,更有利于梳理构效关系,从而获得性能更为优异的绿光辅助层材料。本发明提供的有机发光化合物作为有机电致发光器件的电子传输层材料,与其他电子传输层材料相比,发光效率和寿命均得到了显著的提高。且所述有机发光化合物合成路线较短,工艺简单,原料易得,成本低,适合工业化生产。
Description
技术领域
本发明涉及发光材料技术领域,尤其涉及一种有机发光化合物及其制备方法和有机电致发光器件。
背景技术
OLED材料分为发光材料、空穴传输材料、电子传输材料等;其中,空穴传输材料通常具有低的最高已占据分子轨道(HOMO)值,在发光层中生成的激子扩散到空穴传输层界面或者空穴传输层侧,最终导致在发光层内界面的发光或者发光层内的电荷不均衡,从而在空穴传输层的界面上发光,使有机电致发光器件的色纯度及效率变低,并且寿命变短。向发光层和空穴传输层之间引入发光辅助层,可以有效避免上述技术问题。
但是,目前作为发光辅助层的材料有限,面板产线上的绿光发光辅助层材料大多采用德国默克、韩国三星、日本出光的相关材料,这类材料大多采用芴环结构,它们在具备较高的空穴迁移率,同时具备较高的T1能量阻挡复合后的激子外扩到传输层,提升器件的整体效率,同时合适的HOMO值降低了空穴从传输层到发光层的传输势垒,使得器件驱动电压降低且寿命有所改善。
发明内容
有鉴于此,本发明的目的在于提供一种有机发光化合物及其制备方法和有机电致发光器件,本发明提供的有机发光化合物具有更为精细差异空间构象的分子结构,更有利于梳理构效关系,从而获得性能更为优异的绿光辅助层材料。
本发明提供了一种有机发光化合物,具有式Ⅰ所示结构:
其中,X选自化学键、O、S、Se、Si(R6R7)、C(R8R9)或NR10;
L选自化学键、取代或未经取代的C6~C60的芳基、C3~C60的杂芳基、C10~C60的稠环基或C10~C60的螺环基;
R1-R5独立的选自氢、氘、取代或未经取代的C1-C30烷基、C6-C30芳基、3元到30元杂芳基、C1-C30烷氧基、C1-C30烷巯基、C6-C30芳基氨基或C6-C30芳氧基;
R6-R10独立的选自氢、氘、取代或未经取代的C1-C10烷基、C3-C15环烷烃、C1-C10烷氧基、C6-C30芳基、3元到30元杂芳基、C6-C30芳基氨基或C6-C30芳氧基;
Ar1、Ar2独立的选自取代或未经取代的C1-C30烷基、C6-C30芳基、C1-C30烷氧基、3元到30元的杂芳基、C10-C30稠环基、C5-C30螺环基,或与相邻取代基连接形成单环或多环的C3-C30脂肪族环或C6-C30芳香族环。
进一步,所述L优选选自单键、取代或未经取代的苯基、萘基、菲基、苯并菲基、芘基、苝基、9,9-螺二芴基、(9,9-二烷基)芴基、(9,9-二取代或未取代的芳基)芴基、咔唑基、二苯并噻吩基、二苯并呋喃基、吡啶基、嘧啶基、噻唑基、恶唑基、三氮唑基、喹啉基或喹唑啉基。
进一步,所述R1优选选自甲基、乙基、丙基、异丙基、丁基、叔丁基、烷氧基、烷巯基、芳氧基、苯基、联苯基或萘基。
进一步,所述R2优选选自甲基、乙基、丙基、异丙基、丁基、叔丁基、烷氧基、烷巯基、芳氧基、苯基、联苯基或萘基。
进一步,所述R3优选选自甲基、乙基、丙基、异丙基、丁基、叔丁基、烷氧基、烷巯基、芳氧基、苯基、联苯基或萘基。
更进一步,R1-R3取代基的位置优选在所在苯环的任意位置,R1的个数优选为0~5,R2、R3的个数优选为0~4。
进一步,所述R4优选为氘。
进一步,所述R5优选为氘。
进一步,所述R6优选选自甲基、乙基、萘基、烷氧基、苯基、金刚烷基、联苯基或杂芳基。
进一步,所述R7优选选自甲基、乙基、萘基、烷氧基、苯基、金刚烷基、联苯基或杂芳基。
进一步,所述R8优选选自甲基、乙基、萘基、烷氧基、苯基、金刚烷基、联苯基或杂芳基。
进一步,所述R9优选选自甲基、乙基、萘基、烷氧基、苯基、金刚烷基、联苯基或杂芳基。
进一步,所述R10优选选自甲基、乙基、萘基、烷氧基、苯基、金刚烷基、联苯基或杂芳基。
进一步,所述Ar1优选选自取代或未经取代的萘基、菲基、苯基、甲基苯基、二甲基苯基、三联苯基、联苯、二苯并呋喃、二苯并噻吩、环戊二噻吩、环戊二呋喃或二甲基芴。
进一步,所述Ar2优选选自取代或未经取代的萘基、菲基、苯基、甲基苯基、二甲基苯基、三联苯基、联苯、二苯并呋喃、二苯并噻吩、环戊二噻吩、环戊二呋喃或二甲基芴。
更进一步,Ar1、Ar2中形成的单环或多环的C3-C30脂肪族环或C6-C30芳香族环上的碳原子可置换为氮、氧、硫、硅等杂原子中的一个或以上。
上述技术方案中,术语“取代或未经取代的”意指被选自以下的一个、两个或更多个取代基取代:氘;卤素基团;腈基;羟基;羰基;酯基;甲硅烷基;硼基;经取代或未经取代的烷基;经取代或未经取代的环烷基;经取代或未经取代的烷氧基;经取代或未经取代的烯基;经取代或未经取代的烷基胺基;经取代或未经取代的杂环基胺基;经取代或未经取代的芳基胺基;经取代或未经取代的芳基;和经取代或未经取代的杂环基,或者被以上所示的取代基中的两个或更多个取代基相连接的取代基取代,或者不具有取代基。例如,“两个或更多个取代基相连接的取代基”可以包括联苯基。换言之,联苯基可以为芳基,或者可以解释为两个苯基相连接的取代基。
本发明优选的,所述有机发光化合物,具有以下具体结构:
上述结构式中的单键表示甲基。
本发明还提供了上述有机发光化合物的制备方法,包括以下步骤:
a)将反应物B加入三口瓶中,加入无水四氢呋喃并氮气置换2次~4次,随后将反应体系降温至-80℃~-75℃,滴加n-BuLi,搅拌1h~3h;然后将反应物A溶于四氢呋喃中,滴加至反应体系中,滴加完毕后升温至20℃~30℃搅拌8h~12h;再加入蒸馏水终止反应,分液收集有机相,加入无水硫酸镁干燥,通过旋转蒸发仪除去溶剂,得到中间体C;
b)将中间体C加入三口瓶中,加入三氯甲烷搅拌至充分溶解,加入反应物D和三氟甲磺酸,回流搅拌0.5h~1.5h后,冷却至20℃~30℃;再加入蒸馏水终止反应,分液,收集有机相,加入无水硫酸镁干燥,通过旋转蒸发仪除去溶剂,得到中间体E;
c)将中间体E和反应物F加入到三口瓶中,加入无水甲苯,氮气置换2次~4次,搅拌至充分溶解,随后加入叔丁醇钠、Pd2(dba)3和三叔丁基膦,回流搅拌8h~12h,冷却至20℃~30℃;再加入蒸馏水,分液,水相用二氯甲烷萃取2次~4次,合并有机相,无水硫酸镁干燥,柱层析后得到具有式Ⅰ所示结构的有机发光化合物;
在本发明的一些具体实施例中,所述反应的路线如下:
上述路线中的R1~R10、Ar1、Ar2、X、L的范围与上述技术方案中所述的相同。
进一步,步骤a)中所述反应物B、n-BuLi和反应物A的摩尔比优选为(8~9):10:(8~9),更优选为8.3:10:8.3。
进一步,步骤b)中所述中间体C、反应物D和三氟甲磺酸的摩尔比优选为(6~7):(30~35):13,更优选为6.5:32.5:13。
进一步,步骤c)中所述中间体E、反应物F、叔丁醇钠、Pd2(dba)3和三叔丁基膦的摩尔比优选为(40~50):(45~55):(80~100):(0.04~0.05):(0.2~0.25),更优选为45:50:90:0.045:0.23。
本发明还提供了一种有机电致发光器件,包括上述技术方案所述的有机发光化合物。
所述有机电致发光器件为本领域技术人员熟知的有机电致发光器件即可,本发明优选包括第一电极、第二电极和设置于所述第一电极与第二电极之间的一个或多个有机物层;至少一个所述有机物层包含上述有机发光化合物。
本发明中,所述有机物层是指有机电致发光器件第一电极和第二电极之间的全部层。所述有机物层中的至少一层为发光层。
按照本发明,所述有机物层优选包括空穴注入层、空穴传输层、同时具备空穴注入和空穴传输技能层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层与同时具备电子传输和电子注入技能层中的一层或多层,更优选包括依次设置的空穴注入层、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或依次设置的既具备空穴注入又具备空穴传输技能层、电子阻挡层、发光层、空穴阻挡层与既具备电子传输又具备电子注入技能层。
当本发明有机物层包含空穴注入层、空穴传输层和同时具备空穴注入和空穴传输技能层时,优选所述空穴注入层、空穴传输层和同时具备空穴注入和空穴传输技能层中至少一层包含空穴注入物质、空穴传输物质或既具备空穴注入又具备空穴传输技能的物质。
当本发明有机物层为单层结构时,所述有机物层为发光层,当所述有机物层为多层结构时,所述有机物层包括发光层;所述发光层中优选包括磷光主体、荧光主体、磷光掺杂材料与荧光掺杂材料中的一种或多种。
当所述有机物层包括电子传输层时,所述电子传输层可包括式(I)所示的有机发光化合物。在本发明的一些具体实施例中,所述电子传输层还包括金属化合物。所述金属化合物为本领域技术人员熟知的用于电子传输的物质即可,并无特殊的限制。
当所述有机物层同时包括发光层与电子传输层时,所述发光层与电子传输层可分别包括结构相同或不相同的式(I)所示的有机发光化合物。
本发明提供的有机电致发光器件,利用式(I)所示的有机发光化合物及常规材料制成即可,本发明对所述有机电致发光器件的制备方法并无限定,本领域常规方法即可,本发明优选利用薄膜蒸镀、电子束蒸发或物理气相沉积等方法在基板上蒸镀金属及具有导电性的氧化物及它们的合金形成阳极,然后在其上形成有机物层及蒸镀阴极,得到有机电致发光器件。
所述有机物层可以同时包括上述的空穴注入层、空穴传输层、发光层、空穴阻挡层及电子传输层的多层结构,并且这些多层结构可按照上述薄膜蒸镀、电子束蒸发或物理气相沉积等方法蒸镀,也可使用多样的高分子材料溶剂工程替代蒸镀方法,如旋转涂膜(spin-coating)、薄带成型(tape-casting)、刮片法(doctor-blading)、丝网印刷(Screen-Printing)、喷墨印刷或热成像(Thermal-Imaging)等方法减少层数制造。
本发明提供的有机电致发光器件按照使用的材料也可分为前面发光、背面发光或两面发光;并且该有机电致发光器件可以同样原理应用在有机发光器件(OLED)、有机太阳电池(OSC)、电子纸(e-paper)、有机感光体(OPC)或有机薄膜晶体管(OTFT)上。
本发明提供的式(I)所示的有机发光化合物在有机太阳电池、照明用OLED、柔性OLED、有机感光体及有机晶体管等有机器件中也可按照适用有机发光器件的原理适用。
本发明还提供了一种有机光电材料,包括上述式(I)所示的有机发光化合物;所述有机光电材料包括有机太阳电池、电子纸、有机感光体或有机晶体管。
与现有技术相比,本发明提供了一种有机发光化合物,具有式Ⅰ所示结构。本发明通过在萘环上的不同活性位点与母核和侧链基团连接,极大拓展了结构设计方向,可以设计并合成出具有更为精细差异空间构象的分子结构,更有利于梳理构效关系,从而获得性能更为优异的绿光辅助层材料。本发明提供的有机发光化合物作为有机电致发光器件的电子传输层材料,与其他电子传输层材料相比,发光效率和寿命均得到了显著的提高。且所述有机发光化合物合成路线较短,工艺简单,原料易得,成本低,适合工业化生产。
具体实施方式
为了进一步说明本发明,下面结合实施例对本发明提供的有机发光化合物及其制备方法和有机电致发光器件进行详细描述。
本发明以以下化合物1、40、62、92、119为例,其余化合物的制备方法类似,在此不再另行举例。
实施例1:化合物13的制备
将反应物B-13(83mmol)加入到500mL三口瓶中,加入无水四氢呋喃200mL,氮气置换三次,随后将反应体系降温至-78℃,滴加40mL n-BuLi(2.5M)(100mmol),在-78℃下搅拌2h。将反应物A-13(83mmol)溶于50mL四氢呋喃中,滴加至反应体系中,滴加完毕后升温至室温搅拌10h。加入100mL蒸馏水终止反应,分液收集有机相,加入无水硫酸镁干燥。通过旋转蒸发仪除去溶剂,得到白色中间体C-13(24.4g,产率86%,MS:342.12)。
将中间体C-13(65mmol)加入500mL三口瓶中,加入200mL三氯甲烷搅拌至充分溶解,加入反应物D-13(325mmol)和三氟甲磺酸(130mmol),回流搅拌1h。冷却至室温,加入200mL蒸馏水终止反应,分液,收集有机相,加入无水硫酸镁干燥,通过旋转蒸发仪除去溶剂,得到白色固体中间体E-13(18.6g,产率71%,MS:402.86)。
将中间体E-13(45mmol),反应物F-13(50mmol)加入到500mL三口瓶中,加入无水甲苯200mL,氮气置换三次,搅拌至充分溶解,随后加入叔丁醇钠(90mmol),Pd2(dba)3(0.045mmol),三叔丁基膦(0.23mmol),回流搅拌10h,冷却至室温,加入蒸馏水100mL,分液,水相用二氯甲烷萃取三次,合并有机相,无水硫酸镁干燥,柱层析得到化合物13(27.8g,产率85%,MS:727.34)。
实施例2:化合物40的制备
将反应物B-40(83mmol)加入到500mL三口瓶中,加入无水四氢呋喃200mL,氮气置换三次,随后将反应体系降温至-78℃,滴加40mL n-BuLi(2.5M)(100mmol),在-78℃下搅拌2h。将反应物A-40(83mmol)溶于50mL四氢呋喃中,滴加至反应体系中,滴加完毕后升温至室温搅拌10h。加入100mL蒸馏水终止反应,分液收集有机相,加入无水硫酸镁干燥。通过旋转蒸发仪除去溶剂,得到白色中间体C-40(26.5g,产率83%,MS:384.13)。
将中间体C-40(65mmol)加入500mL三口瓶中,加入200mL三氯甲烷搅拌至充分溶解,加入反应物D-40(325mmol)和三氟甲磺酸(130mmol),回流搅拌1h。冷却至室温,加入200mL蒸馏水终止反应,分液,收集有机相,加入无水硫酸镁干燥,通过旋转蒸发仪除去溶剂,得到白色固体中间体E-40(21.4g,产率74%,MS:444.25)。
将中间体E-40(45mmol),反应物F-40(50mmol)加入到500mL三口瓶中,加入无水甲苯200mL,氮气置换三次,搅拌至充分溶解,随后加入叔丁醇钠(90mmol),Pd2(dba)3(0.045mmol),三叔丁基膦(0.23mmol),回流搅拌10h,冷却至室温,加入蒸馏水100mL,分液,水相用二氯甲烷萃取三次,合并有机相,无水硫酸镁干燥,柱层析得到化合物40(29.1g,产率80%,MS:809.42)。
实施例3:化合物62的制备
将反应物B-62(83mmol)加入到500mL三口瓶中,加入无水四氢呋喃200mL,氮气置换三次,随后将反应体系降温至-78℃,滴加40mL n-BuLi(2.5M)(100mmol),在-78℃下搅拌2h。将反应物A-62(83mmol)溶于50mL四氢呋喃中,滴加至反应体系中,滴加完毕后升温至室温搅拌10h。加入100mL蒸馏水终止反应,分液收集有机相,加入无水硫酸镁干燥。通过旋转蒸发仪除去溶剂,得到白色中间体C-62(25.0g,产率88%,MS:342.20)。
将中间体C-62(65mmol)加入500mL三口瓶中,加入200mL三氯甲烷搅拌至充分溶解,加入反应物D-62(325mmol)和三氟甲磺酸(130mmol),回流搅拌1h。冷却至室温,加入200mL蒸馏水终止反应,分液,收集有机相,加入无水硫酸镁干燥,通过旋转蒸发仪除去溶剂,得到白色固体中间体E-62(19.9g,产率76%,MS:402.65)。
将中间体E-62(45mmol),反应物F-62(50mmol)加入到500mL三口瓶中,加入无水甲苯200mL,氮气置换三次,搅拌至充分溶解,随后加入叔丁醇钠(90mmol),Pd2(dba)3(0.045mmol),三叔丁基膦(0.23mmol),回流搅拌10h,冷却至室温,加入蒸馏水100mL,分液,水相用二氯甲烷萃取三次,合并有机相,无水硫酸镁干燥,柱层析得到化合物62(28.7g,产率82%,MS:780.21)。
实施例4:化合物92的制备
将反应物B-92(83mmol)加入到500mL三口瓶中,加入无水四氢呋喃200mL,氮气置换三次,随后将反应体系降温至-78℃,滴加40mL n-BuLi(2.5M)(100mmol),在-78℃下搅拌2h。将反应物A-92(83mmol)溶于50mL四氢呋喃中,滴加至反应体系中,滴加完毕后升温至室温搅拌10h。加入100mL蒸馏水终止反应,分液收集有机相,加入无水硫酸镁干燥。通过旋转蒸发仪除去溶剂,得到白色中间体C-92(26.5g,产率83%,MS:384.52)。
将中间体C-92(65mmol)加入500mL三口瓶中,加入200mL三氯甲烷搅拌至充分溶解,加入反应物D-92(325mmol)和三氟甲磺酸(130mmol),回流搅拌1h。冷却至室温,加入200mL蒸馏水终止反应,分液,收集有机相,加入无水硫酸镁干燥,通过旋转蒸发仪除去溶剂,得到白色固体中间体E-92(20.2g,产率70%,MS:445.30)。
将中间体E-92(45mmol),反应物F-92(50mmol)加入到500mL三口瓶中,加入无水甲苯200mL,氮气置换三次,搅拌至充分溶解,随后加入叔丁醇钠(90mmol),Pd2(dba)3(0.045mmol),三叔丁基膦(0.23mmol),回流搅拌10h,冷却至室温,加入蒸馏水100mL,分液,水相用二氯甲烷萃取三次,合并有机相,无水硫酸镁干燥,柱层析得到化合物92(31.0g,产率84%,MS:819.36)。
实施例5:化合物119的制备
将反应物B-119(83mmol)加入到500mL三口瓶中,加入无水四氢呋喃200mL,氮气置换三次,随后将反应体系降温至-78℃,滴加40mL n-BuLi(2.5M)(100mmol),在-78℃下搅拌2h。将反应物A-119(83mmol)溶于50mL四氢呋喃中,滴加至反应体系中,滴加完毕后升温至室温搅拌10h。加入100mL蒸馏水终止反应,分液收集有机相,加入无水硫酸镁干燥。通过旋转蒸发仪除去溶剂,得到白色中间体C-119(26.1g,产率82%,MS:384.65)。
将中间体C-119(65mmol)加入500mL三口瓶中,加入200mL三氯甲烷搅拌至充分溶解,加入反应物D-119(325mmol)和三氟甲磺酸(130mmol),回流搅拌1h。冷却至室温,加入200mL蒸馏水终止反应,分液,收集有机相,加入无水硫酸镁干燥,通过旋转蒸发仪除去溶剂,得到白色固体中间体E-119(21.7g,产率73%,MS:458.24)。
将中间体E-119(45mmol),反应物F-119(50mmol)加入到500mL三口瓶中,加入无水甲苯200mL,氮气置换三次,搅拌至充分溶解,随后加入叔丁醇钠(90mmol),Pd2(dba)3(0.045mmol),三叔丁基膦(0.23mmol),回流搅拌10h,冷却至室温,加入蒸馏水100mL,分液,水相用二氯甲烷萃取三次,合并有机相,无水硫酸镁干燥,柱层析得到化合物119(29.3g,产率83%,MS:783.75)。
本发明以上述化合物的制备为例,其余化合物的制备方法同上,在此不再一一例举,部分质谱和分子式列于下表1。
表1本发明实施例制备的化合物质谱和分子式数据
实施例 | 化合物 | 分子式 | 质谱理论值 | 质谱测试值 |
实施例6 | 8 | C<sub>60</sub>H<sub>49</sub>NO | 799.38 | 799.34 |
实施例7 | 18 | C<sub>58</sub>H<sub>47</sub>NSi | 785.35 | 785.26 |
实施例8 | 23 | C<sub>56</sub>H<sub>41</sub>NO | 743.32 | 743.34 |
实施例9 | 35 | C<sub>56</sub>H<sub>41</sub>N | 727.32 | 727.30 |
实施例10 | 45 | C<sub>56</sub>H<sub>39</sub>NO | 741.30 | 741.42 |
实施例11 | 52 | C<sub>60</sub>H<sub>49</sub>NO | 799.38 | 799.32 |
实施例12 | 60 | C<sub>65</sub>H<sub>45</sub>NSi | 867.33 | 867.23 |
实施例13 | 66 | C<sub>55</sub>H<sub>41</sub>NO<sub>3</sub> | 763.31 | 763.21 |
实施例14 | 78 | C<sub>53</sub>H<sub>37</sub>N | 687.29 | 687.33 |
实施例15 | 84 | C<sub>56</sub>H<sub>41</sub>NSe | 807.24 | 807.35 |
实施例16 | 88 | C<sub>59</sub>H<sub>47</sub>N | 769.37 | 769.36 |
实施例17 | 95 | C<sub>53</sub>H<sub>37</sub>NS | 719.26 | 719.29 |
实施例18 | 100 | C<sub>62</sub>H<sub>45</sub>NO | 819.35 | 819.26 |
实施例19 | 108 | C<sub>59</sub>H<sub>39</sub>NOS | 809.28 | 809.33 |
实施例20 | 115 | C<sub>59</sub>H<sub>39</sub>NS | 793.28 | 793.34 |
实施例21 | 118 | C<sub>60</sub>H<sub>49</sub>N | 783.39 | 783.32 |
实施例22 | 123 | C<sub>53</sub>H<sub>37</sub>NS | 719.26 | 719.55 |
实施例23 | 130 | C<sub>57</sub>H<sub>43</sub>N | 741.34 | 741.67 |
[器件实施例1]:制造含有化合物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HT所示化合物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的主体材料EMH和掺杂材料EMD。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10nm的BAlq作为空穴阻挡层及厚度为40nm的电子传输层Alq3。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150nm的铝作为阴极,以此完成了有机电致发光器件的制备。
将器件实施例1中的化合物1分别置换为化合物8,18,23,35,40,45,52,60,62,66,78,84,88,92,95,100,108,115,118,119,123,130其他方法相同,分别制作含有化合物8,18,23,35,40,45,52,60,62,66,78,84,88,92,95,100,108,115,118,119,123,130的有机电致发光器件实施例2-器件实施例23。
[器件对比例1]-[器件对比例4]
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,将发光辅助层的化合物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3:制造含有对比化合物3的有机电致发光器件。
按照器件实施例1的方法,将发光辅助层的化合物1置换为对比化合物3,其他方法相同,制作含有对比化合物3的有机电致发光器件。
器件对比例4:按照器件实施例1的方法,制作器件对比例4。不同之处在于不含有发光辅助层。
对上述制备的有机电致发光器件加以正向直流偏置电压,利用Photo Research公司的PR-650光度测量设备测定有机电致发光特性,并在亮度值为8000cd/m2的基准灰度下利用McScience公司的寿命测定装置测定了T95的寿命。结果见表2。
表2本发明器件实施例1~23以及器件对比例1~4的发光特性测试结果
由表2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比较化合物1-3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,发光效率以及寿命得到显著提高。与器件对比例1-3相比,驱动电压下降1.5V-2.2V,发光效率提升约5.2-16.3%,同时器件寿命也显著提高。
以上实施例的说明只是用于帮助理解本发明的方法及其核心思想。应当指出,对于本技术领域的普通技术人员来说,在不脱离本发明原理的前提下,还可以对本发明进行若干改进和修饰,这些改进和修饰也落入本发明权利要求的保护范围内。
Claims (10)
1.一种有机发光化合物,具有式Ⅰ所示结构:
其中,X选自化学键、O、S、Se、Si(R6R7)、C(R8R9)或NR10;
L选自化学键、取代或未经取代的C6~C60的芳基、C3~C60的杂芳基、C10~C60的稠环基或C10~C60的螺环基;
R1-R5独立的选自氢、氘、取代或未经取代的C1-C30烷基、C6-C30芳基、3元到30元杂芳基、C1-C30烷氧基、C1-C30烷巯基、C6-C30芳基氨基或C6-C30芳氧基;
R6-R10独立的选自氢、氘、取代或未经取代的C1-C10烷基、C3-C15环烷烃、C1-C10烷氧基、C6-C30芳基、3元到30元杂芳基、C6-C30芳基氨基或C6-C30芳氧基;
Ar1、Ar2独立的选自取代或未经取代的C1-C30烷基、C6-C30芳基、C1-C30烷氧基、3元到30元的杂芳基、C10-C30稠环基、C5-C30螺环基,或与相邻取代基连接形成单环或多环的C3-C30脂肪族环或C6-C30芳香族环。
2.根据权利要求1所述的有机发光化合物,其特征在于,所述L选自单键、取代或未经取代的苯基、萘基、菲基、苯并菲基、芘基、苝基、9,9-螺二芴基、(9,9-二烷基)芴基、(9,9-二取代或未取代的芳基)芴基、咔唑基、二苯并噻吩基、二苯并呋喃基、吡啶基、嘧啶基、噻唑基、恶唑基、三氮唑基、喹啉基或喹唑啉基。
3.根据权利要求1所述的有机发光化合物,其特征在于,所述R1、R2、R3独立的选自甲基、乙基、丙基、异丙基、丁基、叔丁基、烷氧基、烷巯基、芳氧基、苯基、联苯基或萘基;
R4为氘;
R5为氘;
R6-R10独立的选自甲基、乙基、萘基、烷氧基、苯基、金刚烷基、联苯基或杂芳基。
4.根据权利要求1所述的有机发光化合物,其特征在于,所述Ar1、Ar2独立的选自取代或未经取代的萘基、菲基、苯基、甲基苯基、二甲基苯基、三联苯基、联苯、二苯并呋喃、二苯并噻吩、环戊二噻吩、环戊二呋喃或二甲基芴。
6.一种权利要求1~5任一项所述的有机发光化合物的制备方法,包括以下步骤:
a)将反应物B加入三口瓶中,加入无水四氢呋喃并氮气置换2次~4次,随后将反应体系降温至-80℃~-75℃,滴加n-BuLi,搅拌1h~3h;然后将反应物A溶于四氢呋喃中,滴加至反应体系中,滴加完毕后升温至20℃~30℃搅拌8h~12h;再加入蒸馏水终止反应,分液收集有机相,加入无水硫酸镁干燥,通过旋转蒸发仪除去溶剂,得到中间体C;
b)将中间体C加入三口瓶中,加入三氯甲烷搅拌至充分溶解,加入反应物D和三氟甲磺酸,回流搅拌0.5h~1.5h后,冷却至20℃~30℃;再加入蒸馏水终止反应,分液,收集有机相,加入无水硫酸镁干燥,通过旋转蒸发仪除去溶剂,得到中间体E;
c)将中间体E和反应物F加入到三口瓶中,加入无水甲苯,氮气置换2次~4次,搅拌至充分溶解,随后加入叔丁醇钠、Pd2(dba)3和三叔丁基膦,回流搅拌8h~12h,冷却至20℃~30℃;再加入蒸馏水,分液,水相用二氯甲烷萃取2次~4次,合并有机相,无水硫酸镁干燥,柱层析后得到具有式Ⅰ所示结构的有机发光化合物;
7.根据权利要求6所述的制备方法,其特征在于,步骤a)中所述反应物B、n-BuLi和反应物A的摩尔比为(8~9):10:(8~9)。
8.根据权利要求6所述的制备方法,其特征在于,步骤b)中所述中间体C、反应物D和三氟甲磺酸的摩尔比为(6~7):(30~35):13。
9.根据权利要求6所述的制备方法,其特征在于,步骤c)中所述中间体E、反应物F、叔丁醇钠、Pd2(dba)3和三叔丁基膦的摩尔比为(40~50):(45~55):(80~100):(0.04~0.05):(0.2~0.25)。
10.一种有机电致发光器件,包括权利要求1~5任意一项所述的有机发光化合物。
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