CN103788087A - 含咪唑[1,2,a]并吡啶基团的蒽类衍生物及其在OLED中的应用 - Google Patents
含咪唑[1,2,a]并吡啶基团的蒽类衍生物及其在OLED中的应用 Download PDFInfo
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- CN103788087A CN103788087A CN201210422794.1A CN201210422794A CN103788087A CN 103788087 A CN103788087 A CN 103788087A CN 201210422794 A CN201210422794 A CN 201210422794A CN 103788087 A CN103788087 A CN 103788087A
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title abstract description 41
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 title description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title 3
- 241001597008 Nomeidae Species 0.000 title 1
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 21
- 238000005401 electroluminescence Methods 0.000 claims abstract description 12
- 239000000463 material Substances 0.000 claims description 53
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 17
- -1 aliphatics alkane Chemical class 0.000 claims description 15
- 239000000758 substrate Substances 0.000 claims description 13
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- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 239000011368 organic material Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 abstract description 16
- 238000005516 engineering process Methods 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 6
- 230000027756 respiratory electron transport chain Effects 0.000 abstract description 5
- 150000001454 anthracenes Chemical class 0.000 abstract description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 abstract 1
- 125000005575 polycyclic aromatic hydrocarbon group Chemical group 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 18
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 17
- 150000004056 anthraquinones Chemical class 0.000 description 17
- 238000000034 method Methods 0.000 description 16
- 239000002994 raw material Substances 0.000 description 15
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 13
- 229910052794 bromium Inorganic materials 0.000 description 13
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- 238000004458 analytical method Methods 0.000 description 10
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- 239000004327 boric acid Substances 0.000 description 3
- BIVHHENFZSOWCE-UHFFFAOYSA-N boric acid;bromobenzene Chemical compound OB(O)O.BrC1=CC=CC=C1 BIVHHENFZSOWCE-UHFFFAOYSA-N 0.000 description 3
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- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
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- DLKQHBOKULLWDQ-UHFFFAOYSA-N 1-bromonaphthalene Chemical compound C1=CC=C2C(Br)=CC=CC2=C1 DLKQHBOKULLWDQ-UHFFFAOYSA-N 0.000 description 2
- APSMUYYLXZULMS-UHFFFAOYSA-N 2-bromonaphthalene Chemical compound C1=CC=CC2=CC(Br)=CC=C21 APSMUYYLXZULMS-UHFFFAOYSA-N 0.000 description 2
- WGOLHUGPTDEKCF-UHFFFAOYSA-N 5-bromopyridin-2-amine Chemical compound NC1=CC=C(Br)C=N1 WGOLHUGPTDEKCF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
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- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 1
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- ZYZCALPXKGUGJI-DDVDASKDSA-M (e,3r,5s)-7-[3-(4-fluorophenyl)-2-phenyl-5-propan-2-ylimidazol-4-yl]-3,5-dihydroxyhept-6-enoate Chemical compound C=1C=C(F)C=CC=1N1C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C(C)C)N=C1C1=CC=CC=C1 ZYZCALPXKGUGJI-DDVDASKDSA-M 0.000 description 1
- KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 1
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- NPRYCHLHHVWLQZ-TURQNECASA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynylpurin-8-one Chemical compound NC1=NC=C2N(C(N(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C NPRYCHLHHVWLQZ-TURQNECASA-N 0.000 description 1
- NTZCFGZBDDCNHI-UHFFFAOYSA-N 2-phenylanthracene-9,10-dione Chemical compound C=1C=C2C(=O)C3=CC=CC=C3C(=O)C2=CC=1C1=CC=CC=C1 NTZCFGZBDDCNHI-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
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- IBXWUOHYYXKGAQ-UHFFFAOYSA-N C=[Br]c(cc1)ccc1C(C(c1ccccc1)Br)=O Chemical compound C=[Br]c(cc1)ccc1C(C(c1ccccc1)Br)=O IBXWUOHYYXKGAQ-UHFFFAOYSA-N 0.000 description 1
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- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
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- 229940077746 antacid containing aluminium compound Drugs 0.000 description 1
- 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 description 1
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 1
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- MEYZYGMYMLNUHJ-UHFFFAOYSA-N tunicamycin Natural products CC(C)CCCCCCCCCC=CC(=O)NC1C(O)C(O)C(CC(O)C2OC(C(O)C2O)N3C=CC(=O)NC3=O)OC1OC4OC(CO)C(O)C(O)C4NC(=O)C MEYZYGMYMLNUHJ-UHFFFAOYSA-N 0.000 description 1
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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Abstract
本发明公开了一种含咪唑[1,2,a]并吡啶基团的蒽类衍生物及其在OLED中的应用。本发明涉及一类如式(I)所示的化合物,其中:Ar选自C6~C30稠环芳烃基团;Ar1、Ar2和Ar3独立地选自H、C1~C20的脂肪族烷、C6~C20的芳香族基团或C4~C30的含有杂原子N或S的芳香杂环基团的其中之一;Ar1和Ar2不能同时为H;n等于1或2。该类有机化合物性质稳定,制备工艺简单,具有较高的载流子迁移率,可用于有机电致发光器件中的电子传输层,能够较明显的降低驱动电压,提高电流效率。
Description
技术领域
本发明涉及一种新型有机材料,尤其涉及一种用于有机电致发光器件的化合物及其在有机电致发光显示技术领域中的应用。
背景技术
电致发光材料和器件经过多年的研究和发展,已经达到了实用化水平。各种材料,例如空穴材料,电子材料,发光材料以及显示器件制备技术,已经取得了长足的进展。同样地,传输能力更强、稳定性更高类型的电子传输材料,在相关文章和专利中都已有报道。一般来说,电子传输材料都是具有大的共轭结构的平面芳香族化合物,它们大多具有较好的接受电子的能力,同时在一定正向偏压下又可以有效的传递电子。使用过的电子传输材料主要有8-羟基喹啉铝类化合物,恶二唑类化合物,喹喔啉类化合物,含腈基的聚合物,其它含氮杂环化合物等(Chem.Mater.2004,16,4556-4573,J Mater.Chem.2005,15,94-106)。目前较新的报道有苯基吡啶基取代的稠环芳烃电子传输材料(申请公布号CN 101891673A,申请公布日2010,11,24),苯并咪唑基团取代的稠环芳烃电子传输材料(公开号特开2011-3793,公开日2011,1,6),等等。这些专利所报道的材料,不同程度地使启亮电压降低,效率提高,但由于材料分子量较小,材料的玻璃化温度较低,在材料使用过程,反复充电放电,材料容易结晶,从而影响材料使用寿命。
因此,开发稳定高效的电子传输材料,从而降低起亮电压,提高器件效率,具有很重要的实际应用价值。
发明内容
本发明的目的在于提供一种新型有机化合物,并将该化合物应用于有机发光功能层作为电子传输材料,进而得到驱动电压低,电流效率高、半衰期较长的有机电致发光器件。
为解决上述技术问题,本发明采用的技术方案如下:
本发明提供的有机化合物含有蒽基团和咪唑并[1,2,a]吡啶基团。蒽具有大的共轭平面可以提供高的电子流动性。而咪唑并[1,2,a]吡啶基团的还原电位比相似结构的纯芳香族要低,有利于接受电子,将缺电子的咪唑并[1,2,a]吡啶基团引入到蒽环上,既提高了化合物的电子迁移率,又降低了整个分子的平面性。同时母核蒽2或9、10为所连接的咪唑并[1,2,a]吡啶基团,通过单键旋转,与蒽处在非平面状态,使得整个分子在空间立体上形成一定程度的扭曲,提高了其成膜性。
本发明提供了一种有机化合物,具有如式(I)和(II)所示的结构:
其中:
Ar选自C6~C30稠环芳烃基团;
Ar1、Ar2和Ar3独立地选自H、C1~C20的脂肪族烷、C6~C20的芳香族基团或C4~C30的含有杂原子N或S的芳香杂环基团的其中之一;
Ar1和Ar2不能同时为H;
n等于1或2。
优选地,所述有机化合物具有如式(III)、式(IV)、式(V)或式(VI)所示的结构:
其中:
Ar选自C6~C30稠环芳烃基团;
Ar1、Ar2和Ar3独立地选自H、C1~C20的脂肪族烷、C6~C20的芳香族基团或C4~C30的含有杂原子N或S的芳香杂环基团的其中之一;
Ar1和Ar2不能同时为H;
n等于1或2。
优选地,所述Ar的优选结构式如下述结构式:
优选地,所述Ar1~Ar3的优选结构式如下述结构式:
优选地,所述的有机化合物的优选结构式如下:
所述的有机化合物在有机电致发光器件中用作电子传输材料。
本发明还提供了一种有机电致发光器件,包括基板,以及依次成型于所述基板上的阳极 层、有机发光功能层和阴极层;
所述有机发光功能层所用材料包括空穴传输材料、有机发光材料以及电子传输材料,所述电子传输材料为具有下述结构式(I)或(II)所示的结构:
其中:
Ar选自C6~C30稠环芳烃基团;
Ar1、Ar2和Ar3独立地选自H、C1~C20的脂肪族烷、C6~C20的芳香族基团或C4~C30的含有杂原子N或S的芳香杂环基团的其中之一;
Ar1和Ar2不能同时为H;
n等于1或2。
本发明还提供了一种有机电致发光器件,包括基板,以及依次成型于所述基板上的阳极层、有机发光功能层和阴极层;
所述有机发光功能层所用材料包括空穴传输材料、有机发光材料以及电子传输材料,所述有机发光功能层所用材料为具有下述结构式具有如式(I)或式(II)所示的结构:
其中:
Ar选自C6~C30稠环芳烃基团;
Ar1、Ar2和Ar3独立地选自H、C1~C20的脂肪族烷、C6~C20的芳香族基团或C4~C30的含有杂原子N或S的芳香杂环基团的其中之一;
Ar1和Ar2不能同时为H;
n等于1或2。
本发明的上述技术方案相比现有技术具有以下优点:
(1)本发明提供的有机化合物具有较高的电子传输性能,成膜性好,所应用的器件在使用温度下具有较高的稳定性。
(2)本发明提供的有机化合物性质稳定,制备工艺简单,具有高的发光效率和载流子迁移率,可用于电致发光元件的电子传输层。
(3)器件实施例11-12表明,在电子传输层中应用本发明的有机化合物作为电子传输材料,制备的器件能有效地降低驱动电压,提高电流效率。
附图说明
为了使本发明的内容更容易被清楚的理解,下面根据本发明的具体实施例并结合附图,对本发明作进一步详细的说明;用Gaussian 03/6-31方法分别测定化合物的最高占有分子轨道的HOMO能级和最低空轨道的LUMO能级。其中,
图1是本发明所述的有机化合物M7的核磁谱图(13C);
图2是本发明所述的有机化合物M10的核磁谱图(13C)。
具体实施方式
本发明中所用的吡啶衍生物、苯基溴代醛酮、芳基硼酸衍生物等基础化工原料均可在国内化工产品市场买到,各种稠环芳烃溴代物、稠环芳烃硼酸衍生物均可用普通有机方法合成。
化合物合成实施例
实施例1化合物1的合成
合成过程共分四步,第一步同于实施例1第一步,只是将原料中的2-氨基-5-溴吡啶换为2氨基吡啶,2-溴-2-苯基苯乙酮换为2-溴-2-(对溴苯基)苯乙酮;第二步同于实施例15中的第一步,只是将其中的2,3-苯基-6-溴咪唑并[1,2,a]吡啶换为2-苯基-3-(对溴苯基)咪唑并[1,2,a]吡啶;第三步同于实施例4第一步,只是将原料中的对溴苯硼酸换为上步合成出的硼酸中间体,合成出蒽醌衍生物中间体;第四步同于实施例1的第二步,只是将原料2,3-二苯基-6-溴咪唑并[1,2,a]吡啶换为1-溴萘,将蒽醌换为本实施例中第三步合成出的蒽醌衍生物中间体,得到化合物30。
产物MS(m/e):698,元素分析(C53H34N2):理论值C:91.09%,H:4.90%,N:4.01%;实测值C:91.05%,H:4.89%,N:4.06%。
实施例2化合物2的合成
使用实施例1的第二步,只是将原料2,3-苯基-6-溴咪唑并[1,2,a]吡啶换为2-溴萘,将蒽醌换为实施例30中第三步合成出的蒽醌衍生物中间体,得到化合物31。
产物MS(m/e):698,元素分析(C53H34N2):理论值C:91.09%,H:4.90%,N:4.01%;实测值C:91.07%,H:4.86%,N:4.07%。
实施例3化合物3的合成
使用实施例1的第二步,只是将原料2,3-苯基-6-溴咪唑并[1,2,a]吡啶换为4-溴联苯,将蒽醌换为实施例30中第三步合成出的蒽醌衍生物中间体,得到化合物32。
产物MS(m/e):750,元素分析(C57H38N2):理论值C:91.17%,H:5.10%,N:3.73%;实测值C:91.20%,H:5.05%,N:3.75%。
使用实施例1的第二步,只是将原料2,3-二苯基-6-溴咪唑并[1,2,a]吡啶换为9-溴菲,将蒽醌换为实施例30中第三步合成出的蒽醌衍生物中间体,得到化合物33。
产物MS(m/e):798,元素分析(C61H38N2):理论值C:91.70%,H:4.79%,N:3.51%; 实测值C:91.71%,H:4.83%,N:3.46%。
实施例5化合物5的合成
合成过程共分四步,第一步同于实施例1第一步,只是将原料中的2-氨基-5-溴吡啶换为2氨基吡啶,2-溴-2-苯基苯乙酮换为2-溴-2-苯基(对溴苯基)乙酮;第二步同于实施例15中的第一步,只是将其中的2,3-苯基-6-溴咪唑并[1,2,a]吡啶换为2-(对溴苯基)-3-苯基咪唑并[1,2,a]吡啶;第三步同于实施例4第一步,只是将原料中的对溴苯硼酸换为上步合成出的硼酸中间体,合成出蒽醌衍生物中间体;第四步同于实施例1的第二步,只是将原料2,3-二苯基-6-溴咪唑并[1,2,a]吡啶换为1-溴萘,将蒽醌换为本实施例中第三步合成出的蒽醌衍生物中间体,得到化合物34。
产物MS(m/e):698,元素分析(C53H34N2):理论值C:91.09%,H:4.90%,N:4.01%;实测值C:91.07%,H:4.87%,N:4.06%。
实施例6化合物6的合成
合成过程同于实施例1的第二步,只是将原料2,3-二苯基-6-溴咪唑并[1,2,a]吡啶换为2-溴萘,将蒽醌换为实施例34中第三步合成出的蒽醌衍生物中间体,得到化合物35。
产物MS(m/e):698,元素分析(C53H34N2):理论值C:91.09%,H:4.90%,N:4.01%;实测值C:91.12%,H:4.85%,N:4.03%。
实施例7化合物7的合成
合成过程同于实施例1的第二步,只是将原料2,3-苯基-6-溴咪唑并[1,2,a]吡啶换为4-溴联苯,将蒽醌换为实施例34中第三步合成出的蒽醌衍生物中间体,得到化合物36。
产物MS(m/e):750,元素分析(C57H38N2):理论值C:91.17%,H:5.10%,N:3.73%;实测值C:91.21%,H:5.08%,N:3.71%。
实施例8化合物8的合成
合成过程同于实施例1的第二步,只是将原料2,3-苯基-6-溴咪唑并[1,2,a]吡啶换为2-苯基-3-(对溴苯基)咪唑并[1,2,a]吡啶,得到化合物38。
产物MS(m/e):714,元素分析(C52H34N4):理论值C:87.37%,H:4.79%,N:7.84%;实测值C:87.40%,H:4.82%,N:7.78%。
实施例9化合物9的合成
合成过程同于实施例1的第二步,只是将原料2,3-苯基-6-溴咪唑并[1,2,a]吡啶换为2-苯基-3-(对溴苯基)咪唑并[1,2,a]吡啶,蒽醌换为2-苯基蒽醌,得到化合物39。
产物MS(m/e):790,元素分析(C58H38N4):理论值C:88.07%,H:4.84%,N:7.08%;实测值C:88.05%,H:4.81%,N:7.14%。
实施例10化合物10的合成
合成过程同于实施例4第一步,只是将原料中的对溴苯硼酸换为4-(2-苯基咪唑并[1,2,a]吡啶-3-基)苯硼酸,将2,3-二苯基-6-溴咪唑并[1,2,a]吡啶换为10,10’-二溴9,9’-联蒽,得到化合物40。
产物MS(m/e):890,元素分析(C66H42N4):理论值C:88.96%,H:4.75%,N:6.29%;实测值C:88.94%,H:4.76%,N:6.30%。
下面是本发明化合物的应用实施例:
实施例11:制备器件OLED-1~OLED-10
制备器件的优选实施方式:
(1)器件设计
为了方便比较这些空穴注入、空穴传输材料的性能,本发明设计了一简单电发光器件(基片/阳极/空穴注入层(HIL)/空穴传输层(HTL)/有机发光层(EL)/电子传输层(ETL)/阴极),仅使用M1~M10作为电子传输材料例证,高效电子传输材料Bphen作为比较材料,AND掺杂TBPe作为发光层材料、NPB作为空穴传输材料。Bphen、NPB、AND和TBPe的结构为:
基片可以使用传统有机发光器件中的基板,例如:玻璃或塑料。在本发明的器件制作中选用玻璃基板,ITO作阳极材料。
空穴传输层可以采用各种三芳胺类材料。在本发明的器件制作中所选用的空穴传输材料是NPB。
阴极可以采用金属及其混合物结构,如Mg:Ag、Ca:Ag等,也可以是电子注入层/金属层结构,如LiF/Al、Li2O/Al等常见阴极结构。在本发明的器件制作中所选用的电子注入材料是LiF,阴极材料是Al。
(2)制作器件OLED-1
将涂布了ITO透明导电层的玻璃板在商用清洗剂中超声处理,在去离子水中冲洗,在丙酮:乙醇混合溶剂中超声除油,在洁净环境下烘烤至完全除去水份,用紫外光和臭氧清洗,并用低能阳离子束轰击表面;
把上述带有阳极的玻璃基片置于真空腔内,抽真空至1×10-5~9×10-3Pa,在上述阳极层膜上真空蒸镀NPB作为空穴传输层,蒸镀速率为0.1nm/s,蒸镀膜厚为40nm;
在空穴传输层之上真空蒸镀发光层,以双源共蒸的方法,蒸镀ADN和TBPe,ADN的蒸镀速率为0.1nm/s,TBPe的蒸镀速率为0.005nm/s,蒸镀总膜厚为30nm;
在发光层之上分别真空蒸镀一层M1~M10或Bphen作为电子传输材料,其蒸镀速率为0.1nm/s,蒸镀总膜厚为20nm;
在电子传输层(ETL)上真空蒸镀LiF和Al层作为器件的阴极,厚度分别为0.5nm和150nm。
按上述方法制备制备OLED-2~OLED-40,仅是改变了作为电子传输材料的化合物。
对比例1
方法同实施例11,将ETL材料换成Bphen。
器件性能见表1(标准器件结构:ITO/NPB(40nm)/ADN:5%wt TBPe(30nm)/ETL材料(20nm)/LiF(0.5nm)/Al(150nm))。
表1
实施例12:制备器件OLED-11和OLED-12
方法同实施例11,,将ETL材料换成M7和M10,并改变ETL厚度。
对比例2
方法同实施例11,将ETL材料换成Bphen,并改变ETL厚度。
器件的性能见表2:(标准器件结构:ITO/NPB(40nm)/ADN:5%wt TBPe(30nm)/ETL材料(厚度nm)/LiF(0.5nm)/Al(150nm))
表2
以上结果表明,本发明的新型有机材料在有机电致发光器件中应用,具有较高的电子传输性能和高的载流子迁移率,且制备工艺简单、易行,作为电子传输层材料,能有效地降低驱动电压,提高电流效率,是性能良好的电子传输材料。
尽管结合实施例对本发明进行了说明,但本发明并不局限于上述实施例,应当理解,在本发明构思的引导下,本领域技术人员可进行各种修改和改进,所附权利要求概括了本发明的范围。
Claims (8)
6.权利要求1所述的有机化合物在有机电致发光器件中用作电子传输材料。
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WO2012141249A1 (ja) * | 2011-04-12 | 2012-10-18 | 富士フイルム株式会社 | 有機電界発光素子 |
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US11751415B2 (en) | 2018-02-02 | 2023-09-05 | Oti Lumionics Inc. | Materials for forming a nucleation-inhibiting coating and devices incorporating same |
US11730012B2 (en) | 2019-03-07 | 2023-08-15 | Oti Lumionics Inc. | Materials for forming a nucleation-inhibiting coating and devices incorporating same |
US11985841B2 (en) | 2020-12-07 | 2024-05-14 | Oti Lumionics Inc. | Patterning a conductive deposited layer using a nucleation inhibiting coating and an underlying metallic coating |
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