CN111848417A - 一种苯并蒽衍生物的有机电致发光化合物及其制备方法和应用 - Google Patents
一种苯并蒽衍生物的有机电致发光化合物及其制备方法和应用 Download PDFInfo
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- CN111848417A CN111848417A CN202010736280.8A CN202010736280A CN111848417A CN 111848417 A CN111848417 A CN 111848417A CN 202010736280 A CN202010736280 A CN 202010736280A CN 111848417 A CN111848417 A CN 111848417A
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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 20
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- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 18
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- 235000019341 magnesium sulphate Nutrition 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 9
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- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 9
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 9
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
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- 229940125904 compound 1 Drugs 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
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- -1 dimethylphenyl Chemical group 0.000 description 2
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- OMBVEVHRIQULKW-DNQXCXABSA-M (3r,5r)-7-[3-(4-fluorophenyl)-8-oxo-7-phenyl-1-propan-2-yl-5,6-dihydro-4h-pyrrolo[2,3-c]azepin-2-yl]-3,5-dihydroxyheptanoate Chemical compound O=C1C=2N(C(C)C)C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C=3C=CC(F)=CC=3)C=2CCCN1C1=CC=CC=C1 OMBVEVHRIQULKW-DNQXCXABSA-M 0.000 description 1
- 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 description 1
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 1
- DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-UHFFFAOYSA-N 0.000 description 1
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- 239000005909 Kieselgur Substances 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
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- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
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- 125000000217 alkyl group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 1
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- 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
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
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- 229940125961 compound 24 Drugs 0.000 description 1
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- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
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- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 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
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged 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
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 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
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Classifications
-
- 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
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/68—Preparation of compounds containing amino groups bound to a carbon skeleton from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
-
- 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
- C07C217/80—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 and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
- C07C217/82—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 and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring
- C07C217/92—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 and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings of the same non-condensed six-membered aromatic ring the nitrogen atom of at least one of the amino groups being further bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
-
- 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
-
- 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
- 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
-
- 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
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Abstract
Description
技术领域
本发明涉及发光材料技术领域,具体涉及一种苯并蒽衍生物的有机电致发光化合物及其制备方法和应用。
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。
因此提供一种发光效率高且使用寿命长的苯并蒽衍生物作为母核并在其上的不同活性位点与侧链相连有机电致发光化合物及其制备方法和应用是本领域技术人员急需解决的技术问题。
发明内容
有鉴于此,本发明提供了一种苯并蒽衍生物作为母核并在其上的不同活性位点与侧链相连获得性能更为优异的发光辅助层材料,可以解决现有有机电致发光装置的发光效率和寿命不理想的技术问题。
为了实现上述目的,本发明采用如下技术方案:
一种苯并蒽衍生物的有机电致发光化合物,所述苯并蒽衍生物的有机电致发光化合物的结构通式如化学式1所示:
其中,X为化学键,或X选自O,S,Si(R4R5),C(R6R7)或NR8;
所述R1-R3各自独立地选自:氢、取代或非取代的C1-C10烷基、取代或非取代的C6-C30芳基、取代或非取代的3元至30元杂芳基、取代或非取代的C10-C30稠环基、取代或非取代的C1-C30烷氧基、取代或非取代的C1-C30烷巯基、取代或非取代的C6-C30芳基氨基、取代或非取代的C6-C30芳氧基;
所述R1-R3各自独立地优选自甲基、乙基、丙基、异丙基、丁基、叔丁基、烷氧基、芳氧基、苯基、联苯基或萘基;R1-R3取代基的位置为在所在苯环的任意位置,R1的个数为0~4,R2、R3的个数为0~3。
所述R4-R8各自独立地选自:取代或非取代的C1-C10烷基、C3-C15环烷烃、取代或非取代的C6-C30芳基、取代或非取代的3元至30元杂芳基、取代或非取代的C10-C30稠环基、取代或非取代的C1-C30烷氧基;
R4-R8各自独立地优选自甲基、乙基、萘基、金刚烷基、联苯基、苯基、杂芳基等;
所述Ar1、Ar2独立地选自:取代或非取代的C1-C30烷基、取代或非取代的C6-C30芳基、取代或非取代的3元至30元的杂芳基、取代或非取代的C10-C30稠环基、取代或非取代的C5-C30螺环基,或Ar1、Ar2各自独立与相邻取代基连接形成单环或多环;
Ar1和Ar2各自独立地优选为萘基、菲基、苯基、甲基苯基、芴基、二甲基苯基、二甲基芴基,三联苯基、联苯、二苯并呋喃、二苯并噻吩及其衍生物。
进一步,所述单环或多环为C3-C30脂肪族环或C6-C30芳香族环;所述脂肪族环或芳香族环中至少一个碳原子置换为氮、氧、硫或硅。
采用上述进一步的有益效果在于:本发明限定的上述基团对苯并蒽母核进行性能修饰,得到的化合物有助于提高器件性能。
所述L为连接键,或L选自取代或非取代的C6-C30芳基、取代或非取代的3元至30元杂芳基、取代或非取代的C10-C30稠环基、取代或非取代的C5-C30螺环基。
在上述技术方案中,术语“取代或非取代的”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;取代或非取代的烷基;经取代或非取代的环烷基;经取代或非取代的烷氧基;经取代或非取代的烯基;经取代或非取代的烷基胺基;经取代或非取代的杂环基胺基;经取代或非取代的芳基胺基;经取代或非取代的芳基;和经取代或非取代的杂环基,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。
在上述技术方案中,优选的有机电致发光化合物选自下述结构中的任意一个:
本发明还提供了上述苯并蒽衍生物的有机电致发光化合物的制备方法,
其中:
L为取代基时合成路线为:
步骤为:(1)将反应物A和反应物B溶于盛有干燥甲苯的反应容器中,在氮气氛围下向反应容器中加入Pd2(dba)3、P(t-Bu)3、t-BuONa,并升温至110℃,搅拌条件下反应10h,反应完成后使用硅藻土趁热抽滤,除去盐和催化剂;然后将滤液冷却至室温并用蒸馏水对滤液进行洗涤;将洗涤液进行分液后保留有机相,并用乙酸乙酯萃取水相,合并有机相和乙酸乙酯萃取相,采用硫酸镁干燥合并后的有机相,再进行旋转式蒸发器去除溶剂;然后采用管柱色谱法纯化剩余物质,得到中间体C;
(2)在氮气氛围下将中间体C、反应物D、四(三苯基膦)钯和碳酸钾分别加入到甲苯、乙醇、水的混合溶剂中,升温至100℃回流反应8h,反应结束后,冷却至室温,待固体析出完毕后,对反应液进行抽滤并用水洗涤除去盐,然后再用乙醇淋洗得到滤饼,对滤饼进行干燥后将滤饼置于1,4-二氧六环中进行重结晶,得到通式I所示的化合物;
或,
L为连接键时合成路线为:
步骤为:(1)将反应物a和反应物b溶于盛有干燥甲苯的反应容器中,在氮气氛围下向反应容器中加入Pd2(dba)3、P(t-Bu)3、t-BuONa,并升温至110℃,并且搅拌混合物反应10h,反应完成后使用硅藻土趁热抽滤,除去盐和催化剂;然后将滤液冷却至室温并用蒸馏水对滤液进行洗涤;将洗涤液进行分液后保留有机相,并用乙酸乙酯萃取水相,合并有机相和乙酸乙酯萃取相,采用硫酸镁干燥合并后的有机相后,进行旋转式蒸发器去除溶剂;然后采用管柱色谱法纯化剩余物质,得到通式I所示的化合物。
进一步,L为取代基时所述反应物A和反应物B的摩尔比为1:1.1;
所述中间体C、反应物D、四(三苯基膦)钯和碳酸钾、摩尔比为1:1.1:0.01:2.4;
L为化学键时所述反应物a和反应物b摩尔比为1:1.1。
进一步,L为取代基或化学键时反应物a与、P(t-Bu)3、t-BuONa的摩尔比为1:0.01-0.02:0.056:3;
反应物a与、P(t-Bu)3、t-BuONa的摩尔比优选为1:0.0112:0.056:3;
采用上述进一步的有益效果在于:在本发明限定的比例下反应得到的产物副产品少,速度快,容易提纯。
进一步,L为取代基或化学键时所述管柱色谱法纯化洗脱剂为二氯甲烷和石油醚;所述二氯甲烷和石油醚体积比为1:9。
采用上述进一步的有益效果在于:本发明限定的洗脱剂比例下,能够有较将杂质点与产物分开,获得纯度很高的物质。
本发明的有益效果在于:本发明有机电致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。
本发明还提供了上述苯并蒽衍生物的有机电致发光化合物在制备有机电致发光器件中的应用。
一种有机电致发光器件,依次包括第一电极、若干个有机物层和第二电极;至少一个所述有机物层上述苯并蒽衍生物的有机电致发光化合物。
进一步,上述有机物层包括空穴注入层、空穴传输层、发光辅助层、空穴注入-空穴传输功能层、发光层、电子传输层、电子注入层的一层或几层,且至少一层包上述有机电致发光化合物;优选所述有机物层中至少一层包含空穴注入物质、空穴传输物质、发光辅助物质或既空穴注入-空穴传输功能层。
所述有机物层为单层结构时,有机物层为发光层,所述有机物层为多层结构时,所述有机物层包括发光层;
采用上述进一步的有益效果在于:本发明不同功能层的搭配使用,使能级搭配更加合理。
更进一步,所述发光层中为磷光主体、荧光主体、磷光掺杂材料和荧光掺杂材料中的一种或多种。当所述有机物层包括空穴传输层或发光辅助层时,所述空穴传输层包括化学式1所示的有机发光化合物。
采用上述进一步的有益效果在于:本发明限定的发光辅助层的使用会使空穴传输层与发光层之间的能级过渡更加平滑,有效降低势垒,降低驱动电压使寿命延长的同时,提高发光效率。
与现有技术相比本发明的有益效果在于:本发明提供的有机电致发光器件具有发光效率高、低驱动电压且寿命较长。
具体实施方式
下面将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:化合物9的制备
在反应容器中加入反应物A-9(50mmol)和反应物B-9(55mmol)溶于200ml甲苯之后,在氮气氛围下加入Pd2(dba)3(0.56mmol)、P(t-Bu)3(2.8mmol)、t-BuONa(150mmol)。添加后,使反应温度缓慢升温到110℃,并且搅拌混合物10h。使用硅藻土趁热抽滤,除去盐和催化剂,滤液冷却至室温后,接着将蒸馏水添加到滤液中进行洗涤,分液后保留有机相,用乙酸乙酯萃取水相。接着使用硫酸镁干燥合并后的有机层,并且使用旋转式蒸发器去除溶剂。以二氯甲烷:石油醚体积比为1:9作为洗脱剂,用管柱色谱法纯化剩余物质,获得终产品9(21.2g,产率为76%,MS:557.27)。
实施例2:化合物24的制备
步骤1:
在反应容器中加入化学式反应物A-24(50mmol)和反应物B-24(55mmol)溶于200ml甲苯之后,在氮气氛围下加入Pd2(dba)3(0.56mmol)、P(t-Bu)3(2.8mmol)、t-BuONa(150mmol)。添加后,使反应温度缓慢升温到110℃,并且搅拌混合物10h。使用硅藻土趁热抽滤,除去盐和催化剂,滤液冷却至室温后,接着将蒸馏水添加到滤液中进行洗涤,分液后保留有机相,用乙酸乙酯萃取水相。接着使用硫酸镁干燥合并后的有机层,并且使用旋转式蒸发器去除溶剂。以二氯甲烷:石油醚体积比为1:9作为洗脱剂,用管柱色谱法纯化剩余物质,获得中间体C-24(27.6g,产率为78%)。
步骤2:
N2保护下,将中间体C-24(35mmol)、中间体D-24(38.5mmol)、四(三苯基膦)钯(0.35mmol)和碳酸钾(84mmol)分别加入到150mL甲苯、50mL乙醇、50mL水的混合溶剂中,升温至100℃回流反应8h,反应结束后,冷却至室温,待固体析出完毕后,抽滤后用水洗涤出去盐,再用少量乙醇淋洗,干燥滤饼。置于1,4-二氧六环中重结晶(150mL),得到终产品24(27.3g,86%,MS:906.40)。
实施例3:化合物41的制备
步骤1:
在反应容器中加入化学式反应物A-41(50mmol)和反应物B-41(55mmol)溶于200ml甲苯之后,在氮气氛围下加入Pd2(dba)3(0.56mmol)、P(t-Bu)3(2.8mmol)、t-BuONa(150mmol)。添加后,使反应温度缓慢升温到110℃,并且搅拌混合物10h。使用硅藻土趁热抽滤,除去盐和催化剂,滤液冷却至室温后,接着将蒸馏水添加到滤液中进行洗涤,分液后保留有机相,用乙酸乙酯萃取水相。接着使用硫酸镁干燥合并后的有机层,并且使用旋转式蒸发器去除溶剂。以二氯甲烷:石油醚体积比为1:9作为洗脱剂,用管柱色谱法纯化剩余物质,获得中间体C-41(19.5g,产率为75%)。
步骤2:
N2保护下,将中间体C-41(35mmol)、中间体D-41(38.5mmol)、四(三苯基膦)钯(0.35mmol)和碳酸钾(84mmol)分别加入到150mL甲苯、50mL乙醇、50mL水的混合溶剂中,升温至100℃回流反应8h,反应结束后,冷却至室温,待固体析出完毕后,抽滤后用水洗涤出去盐,再用少量乙醇淋洗,干燥滤饼。置于1,4-二氧六环中重结晶(150mL),得到终产品41(24.5g,83%,MS:843.39)。
实施例4:化合物63的制备
步骤1:
在反应容器中加入化学式反应物A-63(50mmol)和反应物B-63(55mmol)溶于200ml甲苯之后,在氮气氛围下加入Pd2(dba)3(0.56mmol)、P(t-Bu)3(2.8mmol)、t-BuONa(150mmol)添加后,使反应温度缓慢升温到110℃,并且搅拌混合物10h。使用硅藻土趁热抽滤,除去盐和催化剂,滤液冷却至室温后,接着将蒸馏水添加到滤液中进行洗涤,分液后保留有机相,用乙酸乙酯萃取水相。接着使用硫酸镁干燥合并后的有机层,并且使用旋转式蒸发器去除溶剂。以二氯甲烷:石油醚体积比为1:9作为洗脱剂,用管柱色谱法纯化剩余物质,获得中间体C-63(20.1g,产率为72%)。
步骤2:
N2保护下,将中间体C-63(35mmol)、中间体D-63(38.5mmol)、四(三苯基膦)钯(0.35mmol)和碳酸钾(84mmol)分别加入到150mL甲苯、50mL乙醇、50mL水的混合溶剂中,升温至100℃回流反应8h,反应结束后,冷却至室温,待固体析出完毕后,抽滤后用水洗涤出去盐,再用少量乙醇淋洗,干燥滤饼。置于1,4-二氧六环中重结晶(150mL),得到终产品63(21.4g,82%,MS:745.28)。
实施例5:化合物84的制备
步骤1:
在反应容器中加入化学式反应物A-84(50mmol)和反应物B-84(55mmol)溶于200ml甲苯之后,在氮气氛围下加入Pd2(dba)3(0.56mmol)、P(t-Bu)3(2.8mmol)、t-BuONa(150mmol)。添加后,使反应温度缓慢升温到110℃,并且搅拌混合物10h。使用硅藻土趁热抽滤,除去盐和催化剂,滤液冷却至室温后,接着将蒸馏水添加到滤液中进行洗涤,分液后保留有机相,用乙酸乙酯萃取水相。接着使用硫酸镁干燥合并后的有机层,并且使用旋转式蒸发器去除溶剂。以二氯甲烷:石油醚体积比为1:9作为洗脱剂,用管柱色谱法纯化剩余物质,获得中间体C-84(20.4g,产率为77%)。
步骤2:
N2保护下,将中间体C-84(35mmol)、中间体D-84(38.5mmol)、四(三苯基膦)钯(0.35mmol)和碳酸钾(84mmol)分别加入到150mL甲苯、50mL乙醇、50mL水的混合溶剂中,升温至100℃回流反应8h,反应结束后,冷却至室温,待固体析出完毕后,抽滤后用水洗涤出去盐,再用少量乙醇淋洗,干燥滤饼。置于1,4-二氧六环中重结晶(150mL),得到终产品84(21.1g,84%,MS:717.30)。
实施例6:化合物105的制备
步骤1:
在反应容器中加入化学式反应物A-105(50mmol)和反应物B-105(55mmol)溶于200ml甲苯之后,在氮气氛围下加入Pd2(dba)3(0.56mmol)、P(t-Bu)3(2.8mmol)、t-BuONa(150mmol)。添加后,使反应温度缓慢升温到110℃,并且搅拌混合物10h。使用硅藻土趁热抽滤,除去盐和催化剂,滤液冷却至室温后,接着将蒸馏水添加到滤液中进行洗涤,分液后保留有机相,用乙酸乙酯萃取水相。接着使用硫酸镁干燥合并后的有机层,并且使用旋转式蒸发器去除溶剂。以二氯甲烷:石油醚体积比为1:9作为洗脱剂,用管柱色谱法纯化剩余物质,获得中间体C-105(23.7g,产率为73%)。
步骤2:
N2保护下,将中间体C-105(35mmol)、中间体D-105(38.5mmol)、四(三苯基膦)钯(0.35mmol)和碳酸钾(84mmol)分别加入到150mL甲苯、50mL乙醇、50mL水的混合溶剂中,升温至100℃回流反应8h,反应结束后,冷却至室温,待固体析出完毕后,抽滤后用水洗涤出去盐,再用少量乙醇淋洗,干燥滤饼。置于1,4-二氧六环中重结晶(150mL),得到终产品105(25.4g,81%)。
其他化合物的合成方法均与上述所列举的实施例相同,所以在此不再一一例举,部分质谱和分子式列于下表1。
表1:
[器件实施例1]:制造含有化合物5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的化合物NPB与F4-TCNQ(掺杂比为97:3)作为空穴注入层。然后将化合物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5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CBP和掺杂材料(btfmp)2Ir(dbm)。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5分别置换为化合物9,18,20,24,32,41,50,56,61,63,69,72,73,74,78,83,87,90,95,96,97,100,105,108,110,118,121,123其他方法相同,分别制作含有化合物9,18,20,24,32,41,50,56,61,63,69,72,73,74,78,83,87,90,95,96,97,100,105,108,110,118,121,123的有机电致发光器件实施例2-器件实施例29。
[器件对比例1]-[器件对比例3]
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5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5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:按照器件实施例1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2为本发明器件实施例1~27以及器件对比例1~3的发光特性测试结果(亮度值为5000cd/m2)。
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。
器件实施例18,20,24,32,41,56,61,63,69,72,78,83,87,90,95,100,105,108,110,118,121,123与对比例1-2相比,驱动电压下降约2.0V,发光效率提升约7-15%,同时器件寿命提高约30h。
器件实施例5,9,50,73,74,96,97与对比例1-2相比,得到的数据虽有提升,但是效果并不显著,驱动电压下降在1V左右,发光效率提升约4%,同时器件寿命提高约20h。
相同的母核与相同的器件制备方式得到的器件数据出现明显差异的原因可能是因为侧链结构中带有的“L”连接基团,L的存在使化合物的HUMO能级与发光层和空穴注入层的能级控制在一个更加匹配的区间之内,在有效降低势垒提升发光效率的同时降低驱动电压,延长器件寿命。
对比化合物1-2带有“L”连接键,区别在于母核不同,但是得到的器件数据效果要远低于本发明化合物,可能是因为本文母核中引入了更多的π键,得到的化合物空间构型更加适用于红光辅助材料。
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。
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者使用本发明。对这些实施例的多种修改对本领域的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,在其他实施例中实现。因此,本发明将不会被限制与本文所示的这些实施例,而是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 (10)
1.一种苯并蒽衍生物的有机电致发光化合物,其特征在于,所述苯并蒽衍生物的有机电致发光化合物的结构通式如化学式1所示:
其中,X为化学键,或X选自O,S,Si(R4R5),C(R6R7)或NR8;
所述R1-R3各自独立地选自:氢、取代或非取代的C1-C10烷基、取代或非取代的C6-C30芳基、取代或非取代的3元至30元杂芳基、取代或非取代的C10-C30稠环基、取代或非取代的C1-C30烷氧基、取代或非取代的C1-C30烷巯基、取代或非取代的C6-C30芳基氨基、取代或非取代的C6-C30芳氧基;
所述R4-R8各自独立地选自:取代或非取代的C1-C10烷基、C3-C15环烷烃、取代或非取代的C6-C30芳基、取代或非取代的3元至30元杂芳基、取代或非取代的C10-C30稠环基、取代或非取代的C1-C30烷氧基;
所述Ar1、Ar2独立地选自:取代或非取代的C1-C30烷基、取代或非取代的C6-C30芳基、取代或非取代的3元至30元的杂芳基、取代或非取代的C10-C30稠环基、取代或非取代的C5-C30螺环基,或Ar1、Ar2各自独立与相邻取代基连接形成单环或多环;
所述L为连接键,或L选自取代或非取代的C6-C30芳基、取代或非取代的3元至30元杂芳基、取代或非取代的C10-C30稠环基、取代或非取代的C5-C30螺环基。
2.根据权利要求1所述一种苯并蒽衍生物的有机电致发光化合物,其特征在于,所述单环或多环为C3-C30脂肪族环或C6-C30芳香族环;
所述脂肪族环或芳香族环中至少一个碳原子置换为氮、氧、硫或硅。
3.一种苯并蒽衍生物的有机电致发光化合物的制备方法,其特征在于,
L为取代基时合成路线为:
步骤为:(1)将反应物A和反应物B溶于盛有干燥甲苯的反应容器中,在氮气氛围下向反应容器中加入Pd2(dba)3、P(t-Bu)3、t-BuONa,并升温至110℃,在搅拌条件下反应10h,反应完成后使用硅藻土趁热抽滤,除去盐和催化剂;然后将滤液冷却至室温并用蒸馏水对滤液进行洗涤;将洗涤液进行分液后保留有机相,并用乙酸乙酯萃取水相,合并有机相和乙酸乙酯萃取相,采用硫酸镁干燥合并后的有机相,再进行旋转式蒸发器去除溶剂;然后采用管柱色谱法纯化剩余物质,得到中间体C;
(2)在氮气氛围下将中间体C、反应物D、四(三苯基膦)钯和碳酸钾分别加入到甲苯、乙醇、水的混合溶剂中,升温至100℃回流反应8h,反应结束后,冷却至室温,待固体析出完毕后,对反应液进行抽滤并用水洗涤除去盐,然后再用乙醇淋洗得到滤饼,对滤饼进行干燥后将滤饼置于1,4-二氧六环中进行重结晶,得到通式I所示的化合物;
或,
L为连接键时合成路线为:
步骤为:(1)将反应物a和反应物b溶于盛有干燥甲苯的反应容器中,在氮气氛围下向反应容器中加入Pd2(dba)3、P(t-Bu)3、t-BuONa,并升温至110℃,并且搅拌混合物反应10h,反应完成后使用硅藻土趁热抽滤,除去盐和催化剂;然后将滤液冷却至室温并用蒸馏水对滤液进行洗涤;将洗涤液进行分液后保留有机相,并用乙酸乙酯萃取水相,合并有机相和乙酸乙酯萃取相,采用硫酸镁干燥合并后的有机相后,进行旋转式蒸发器去除溶剂;然后采用管柱色谱法纯化剩余物质,得到通式I所示的化合物。
4.根据权利要求3所述一种苯并蒽衍生物的有机电致发光化合物的制备方法,其特征在于,L为取代基时所述反应物A和反应物B的摩尔比为1:1.1;
所述中间体C、反应物D、四(三苯基膦)钯和碳酸钾的摩尔比为1:1.1:0.01:2.4;
L为化学键时所述反应物a和反应物b摩尔比为1:1.1。
5.根据权利要求3所述一种苯并蒽衍生物的有机电致发光化合物的制备方法,L为取代基或化学键时反应物a与、P(t-Bu)3、t-BuONa的摩尔比为1:0.01-0.02:0.056:3。
6.根据权利要求3所述一种苯并蒽衍生物的有机电致发光化合物的制备方法,其特征在于,L为取代基或化学键时所述管柱色谱法纯化洗脱剂为二氯甲烷和石油醚;
所述二氯甲烷和石油醚的体积比为1:9。
7.一种根据权利要求1或2所述苯并蒽衍生物的有机电致发光化合物在制备有机电致发光器件中的应用。
8.一种有机电致发光器件,其特征在于,依次包括第一电极、若干层有机物层和第二电极;至少一个所述有机物层包括权利要求1或2所述苯并蒽衍生物的有机电致发光化合物。
9.根据权利要求8所述一种有机电致发光器件,其特征在于,所述有机物层包括空穴注入层、空穴传输层、发光辅助层、空穴注入-空穴传输功能层、发光层、电子传输层、电子注入层的一层或几层,且至少一层包括权利要求1或2所述有机电致发光化合物。
10.根据权利要求9所述一种有机电致发光器件,其特征在于,所述发光层中为磷光主体材料、荧光主体材料、磷光掺杂材料和荧光掺杂材料中的一种或多种。
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