CN108727202B - 一种化合物及其制备方法和应用 - Google Patents
一种化合物及其制备方法和应用 Download PDFInfo
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- CN108727202B CN108727202B CN201810598647.7A CN201810598647A CN108727202B CN 108727202 B CN108727202 B CN 108727202B CN 201810598647 A CN201810598647 A CN 201810598647A CN 108727202 B CN108727202 B CN 108727202B
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 40
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
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- 125000003118 aryl group Chemical group 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 12
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- 238000005036 potential barrier Methods 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
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- 238000002390 rotary evaporation Methods 0.000 description 1
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
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- 238000005507 spraying Methods 0.000 description 1
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- 238000003786 synthesis reaction Methods 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- RUVINXPYWBROJD-ONEGZZNKSA-N trans-anethole Chemical compound COC1=CC=C(\C=C\C)C=C1 RUVINXPYWBROJD-ONEGZZNKSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
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- 239000000080 wetting agent Substances 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
- 239000011787 zinc oxide Substances 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/20—Nitrogen atoms
-
- 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
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
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Abstract
本发明提供了一种化合物及其制备方法和应用,实验结果表明,本发明提供的化合物作为有机电致发光器件中的CPL层,能够显著的提高有机电致发光器件的发光效率以及寿命;此外,本发明所述的化合物与高聚物组合得到的油墨组合物易于形成激基络合物,其作为有机电致发光器件的发光层材料时,可以通过印刷工艺实现发光层的涂覆,且得到的发光器件的发光效率和寿命较高。
Description
技术领域
本发明涉及有机光电材料技术领域,尤其是涉及一种化合物及其制备方法和应用。
背景技术
有机电致发光器件的相关研究初始于19世纪60年代,直到80年代末OLED才蓬勃发展起来。OLED具有全固态、低压驱动、主动发光、响应快速、宽视角、发光面积大、发光波长覆盖整个可见光区以及色彩丰富等优点,在实现全色大面积显示领域具有很大的优势,成为极具前景的平板显示器件。有机电致发光器件的发光亮度正比于空穴和电子的浓度及激子的复合概率的乘积,想要获得较高的发光效率,不仅需要空穴和电子能够有效注入、传输及复合且要求空穴和电子注入达到平衡。因此,在有机电致发光器件中,有机层之间及有机层与两电极的能带匹配对器件复合发光非常重要。
为了优化和平衡器件的各项性能,人们引入了多种不同作用的功能层,例如空穴注入层、空穴阻挡层等。在ITO阳极和空穴传输层之间加入空穴注入层的作用主要表现在降低界面势垒、增加空穴传输层与ITO电极的黏附能力、提高其稳定性以及平衡电子和空穴注入等方面。
此外,由于OLED的外量子效率与内量子效率之间存在巨大的差距,极大的制约了OLED的发展,因此,如何提高OLED的光取出效率也成为研究的热点。ITO薄膜和玻璃衬底的界面以及玻璃衬底与空气的界面处会发生全反射,出射到OLED器件前向外部空间的光约占有机材料薄膜EL总量的20%,其余约80%的光主要以导波形式限制在有机材料薄膜、ITO薄膜和玻璃衬底中,严重制约了OLED的发展与应用,如何减少OLED器件中的全反射效应、提高光耦合到器件前向外部空间的比例引,进而提高器件的性能起了人们的广泛关注。
发明内容
有鉴于此,本发明所要解决的技术问题在于提供一种化合物及其制备方法和应用,本发明提供的化合物作为OLED器件的CPL层,能够提高发光器件的效率。
本发明还提供了一种化合物,具有式(I)所示结构,
其中,所述Ar1、Ar2独立的选自氢、C1~C8的烷基、C6~C25的芳基或C2~C20的杂芳基;
所述X1-a、X1-b、X1-c、X1-d、X1-e独立的选自氮或碳;
所述X2-a、X2-b、X2-c、X2-d、X2-e独立的选自氮或碳;
所述R1、R2独立的选自C5~C9的烷基。
优选的,所述Ar1选自氢、C1~C5的烷基、苯基、C1~C5烷基取代的苯基、C10~20的稠环芳基、C3~C15的含硫杂芳基或C3~C15的含氮杂芳基;
所述Ar2选自氢、C1~C5的烷基、苯基、C1~C5的烷基取代的苯基、C10~20的稠环芳基、C3~C15的含硫杂芳基或C3~C15的含氮杂芳基。
优选的,所述Ar1选自氢、甲基、乙基、丙基、正丁基、叔丁基、戊基、三氟甲基、苯基、蒽基、萘基、菲基、3-叔丁基苯基、3-三氟甲基苯基、3-正丙基苯基、3-异丙基苯基、3-甲基苯基、4-叔丁基苯基、4-三氟甲基苯基、4-正丙基苯基、4-异丙基苯基、4-甲基苯基、3,5-二甲基苯基、2-噻吩基、吡啶基、哒嗪基、吡嗪基、三嗪基或吖啶基;
所述Ar2选自氢、甲基、乙基、丙基、正丁基、叔丁基、戊基、三氟甲基、苯基、蒽基、萘基、菲基、3-叔丁基苯基、3-三氟甲基苯基、3-正丙基苯基、3-异丙基苯基、3-甲基苯基、4-叔丁基苯基、4-三氟甲基苯基、4-正丙基苯基、4-异丙基苯基、4-甲基苯基、3,5-二甲基苯基、2-噻吩基、吡啶基、哒嗪基、吡嗪基、三嗪基或吖啶基。
优选的,所述X1-a、X1-b、X1-c、X1-d、X1-e中至多有3个为氮;
所述X2-a、X2-b、X2-c、X2-d、X2-e中至多有3个为氮。
优选的,所述R1、R2独立的选自正戊基、正己基、正庚基、正辛基或正癸基。
优选的,所述式(I)所示的化合物为式(I-1)、式(I-2)或式(I-3),
其中,所述Ar1、Ar2独立的选自氢、C1~C8的烷基、C6~C25的芳基或C2~C20的杂芳基;
所述X1-a、X1-b、X1-c、X1-d、X1-e独立的选自氮或碳;
所述X2-a、X2-b、X2-c、X2-d、X2-e独立的选自氮或碳。
优选的,所述式(I)所示的化合物为式(001)~式(072),
本发明提供了一种式(I)化合物的制备方法,包括:将式(II)结构的化合物与式(III)结构的化合物反应,得到式(I)结构的化合物;
其中,所述Ar1、Ar2独立的选自氢、C1~C8的烷基、C6~C25的芳基或C2~C20的杂芳基;
所述X1-a、X1-b、X1-c、X1-d、X1-e独立的选自氮或碳;
所述X2-a、X2-b、X2-c、X2-d、X2-e独立的选自氮或碳;
所述R1、R2独立的选自C5~C9的烷基。
本发明还提供了一种本发明所述的式(I)所示的化合物作为CPL层在制备有机电致发光器件中的应用。
本发明还提供了一种油墨组合物,包括:高聚物和本发明所述的式(I)所示的化合物。
本发明还提供了一种有机电致发光器件,其中,所述有机电致发光器件的发光层是通过印刷工艺制备得到的;
所述有机电致发光器件的发光层的发光材料包括本发明所述的油墨组合物。
与现有技术相比,本发明提供了一种化合物及其制备方法和应用,实验结果表明,本发明提供的化合物作为有机电致发光器件中的CPL层,能够显著的提高有机电致发光器件的发光效率以及寿命;此外,本发明所述的化合物与高聚物组合得到的油墨组合物易于形成激基络合物,其作为有机电致发光器件的发光层材料时,可以通过印刷工艺实现发光层的涂覆,且得到的发光器件的发光效率和寿命较高。
具体实施方式
本发明提供了一种化合物,具有式(I)所示结构,
其中,所述Ar1、Ar2独立的选自氢、C1~C8的烷基、C6~C25的芳基或C2~C20的杂芳基;
所述X1-a、X1-b、X1-c、X1-d、X1-e独立的选自氮或碳,且所述X1-a、X1-b、X1-c、X1-d、X1-e中至少有1个为氮;
所述X2-a、X2-b、X2-c、X2-d、X2-e独立的选自氮或碳,且所述X2-a、X2-b、X2-c、X2-d、X2-e中至少有1个为氮;
所述R1、R2独立的选自C5~C9的烷基。
按照本发明,所述Ar1优选为氢、C1~C5的烷基、苯基、C1~C5烷基取代的苯基、C10~20的稠环芳基、C3~C15的含硫杂芳基或C3~C15的含氮杂芳基;更优选为氢、甲基、乙基、丙基、正丁基、叔丁基、戊基、三氟甲基、苯基、蒽基、萘基、菲基、3-叔丁基苯基、3-三氟甲基苯基、3-正丙基苯基、3-异丙基苯基、3-甲基苯基、4-叔丁基苯基、4-三氟甲基苯基、4-正丙基苯基、4-异丙基苯基、4-甲基苯基、3,5-二甲基苯基、2-噻吩基、吡啶基、哒嗪基、吡嗪基、三嗪基或吖啶基;所述Ar2优选为氢、C1~C5的烷基、苯基、C1~C5烷基取代的苯基、C10~20的稠环芳基、C3~C15的含硫杂芳基或C3~C15的含氮杂芳基;更优选为氢、甲基、乙基、丙基、正丁基、叔丁基、戊基、三氟甲基、苯基、蒽基、萘基、菲基、3-叔丁基苯基、3-三氟甲基苯基、3-正丙基苯基、3-异丙基苯基、3-甲基苯基、4-叔丁基苯基、4-三氟甲基苯基、4-正丙基苯基、4-异丙基苯基、4-甲基苯基、3,5-二甲基苯基、2-噻吩基、吡啶基、哒嗪基、吡嗪基、三嗪基或吖啶基。
按照本发明,X1-a、X1-b、X1-c、X1-d、X1-e中优选有零个氮、一个为氮、两个为氮或者三个为氮;所述X2-a、X2-b、X2-c、X2-d、X2-e中优选有零个氮、一个为氮、两个为氮或者三个为氮。
按照本发明,所述R1优选为正戊基、正己基、正庚基、正辛基或正癸基。
所述R2优选为正戊基、正己基、正庚基、正辛基或正癸基。
具体的,所述式(I)所示的化合物为式(I-1)、式(I-2)或式(I-3),
其中,所述Ar1、Ar2独立的选自氢、C1~C8的烷基、C6~C25的芳基或C2~C20的杂芳基;
所述X1-a、X1-b、X1-c、X1-d、X1-e独立的选自氮或碳,且所述X1-a、X1-b、X1-c、X1-d、X1-e中至少有1个为氮;
所述X2-a、X2-b、X2-c、X2-d、X2-e独立的选自氮或碳,且所述X2-a、X2-b、X2-c、X2-d、X2-e中至少有1个为氮。
更具体的,所述式(I)所示的化合物为式(001)~式(072),
本发明还提供了一种式(I)化合物的制备方法,包括:将式(II)结构的化合物与式(III)结构的化合物反应,得到式(I)结构的化合物;
其中,所述Ar1、Ar2独立的选自氢、C1~C8的烷基、C6~C25的芳基或C2~C20的杂芳基;
所述X1-a、X1-b、X1-c、X1-d、X1-e独立的选自氮或碳;
所述X2-a、X2-b、X2-c、X2-d、X2-e独立的选自氮或碳;
所述R1、R2独立的选自C5~C9的烷基。
其中,本发明对反应的条件没有特殊要求,本领域技术人员可以根据公知常识选择合适的反应条件制备得到产物,且基团的限定与前述化合物相同。
本发明还提供了一种油墨组合物,包括:高聚物和本发明所述的式(I)所示的化合物。
其中,本发明对高聚物没有特殊要求,本领域公知的可用于油墨组合物的高聚物均可,优选的,所述高聚物为高聚物1、高聚物2或高聚物3,
本发明中,本发明所述的油墨组合物在工作温度或在25℃下的表面张力优选约在19dyne/cm到50dyne/cm范围;更优选是在22dyne/cm到35dyne/cm范围;最优选是在25dyne/cm到33dyne/cm范围。
本发明中,所述油墨组合物在工作温度或25℃下的粘度优选在1cps到100cps范围;更优选在在1cps到50cps范围;最优选在1.5cps到20cps范围;最好是在4.0cps到20cps范围。如此配制的组合物将便于喷墨印刷。
本发明所述的组合物的粘度可以通过不同的方法调节,如通过合适的溶剂选取和油墨中功能材料的浓度进行调节;
本发明中,所述油墨组合物至少还包括一种有机溶剂,其中,所述有机溶剂选自基于芳族或杂芳族的溶剂,特别是脂肪族链/环取代的芳族溶剂、或芳族酮溶剂,或芳族醚溶剂。
适合本发明的溶剂的例子有,但不限于:基于芳族或杂芳族的溶剂:对二异丙基苯、戊苯、四氢萘、环己基苯、氯萘、1,4-二甲基萘、3-异丙基联苯、对甲基异丙苯、二戊苯、三戊苯、戊基甲苯、邻二甲苯、间二甲苯、对二甲苯、邻二乙苯、间二乙苯、对二乙苯、1,2,3,4-四甲苯、1,2,3,5-四甲苯、1,2,4,5-四甲苯、丁苯、十二烷基苯、二己基苯、二丁基苯、对二异丙基苯、1-甲氧基萘、环己基苯、二甲基萘、3-异丙基联苯、对甲基异丙苯、1-甲基萘、1,2,4-三氯苯、1,3-二丙氧基苯、4,4-二氟二苯甲烷、1,2-二甲氧基-4-(1-丙烯基)苯、二苯甲烷、2-苯基吡啶、3-苯基吡啶、N-甲基二苯胺、4-异丙基联苯、d,α-二氯二苯甲烷、4-(3-苯基丙基)吡啶、苯甲酸苄酯、1,1-双(3,4-二-甲基苯基)乙烷、2-异丙基萘、二苄醚等;基于酮的溶剂:1-四氢萘酮,2-四氢萘酮,2-(苯基环氧)四氢萘酮,6-(甲氧基)四氢萘酮,苯乙酮、苯丙酮、二苯甲酮、及它们的衍生物,如4-甲基苯乙酮、3-甲基苯乙酮、2-甲基苯乙酮、4-甲基苯丙酮、3-甲基苯丙酮、2-甲基苯丙酮,异佛尔酮、2,6,8-三甲基-4-壬酮、葑酮、2-壬酮、3-壬酮、5-壬酮、2-癸酮、2,5-己二酮、佛尔酮、二正戊基酮;芳族醚溶剂:3-苯氧基甲苯、丁氧基苯、苄基丁基苯、对茴香醛二甲基乙缩醛、四氢-2-苯氧基-2H-吡喃、1,2-二甲氧基-4-(1-丙烯基)苯、1,4-苯并二噁烷、1,3-二丙基苯、2,5-二甲氧基甲苯、4-乙基本乙醚、1,2,4-三甲氧基苯、4-(1-丙烯基)-1,2-二甲氧基苯、1,3-二甲氧基苯、缩水甘油基苯基醚、二苄基醚、4-叔丁基茴香醚、反式-对丙烯基茴香醚、1,2-二甲氧基苯、1-甲氧基萘、二苯醚、2-苯氧基甲醚、2-苯氧基四氢呋喃、乙基-2-萘基醚、戊醚c己醚、二辛醚、乙二醇二丁醚、二乙二醇二乙醚、二乙二醇丁基甲醚、二乙二醇二丁醚、三乙二醇二甲醚、三乙二醇乙基甲醚、三乙二醇丁基甲醚、三丙二醇二甲醚、四乙二醇二甲醚;酯溶剂:辛酸烷酯、癸二酸烷酯、硬脂酸烷酯、苯甲酸烷酯、苯乙酸烷酯、肉桂酸烷酯、草酸烷酯、马来酸烷酯、烷内酯、油酸烷酯等。
进一步,按照本发明的油墨组合物,所述油墨组合物中的溶剂还可选自:脂肪族酮,例如,2-壬酮、3-壬酮、5-壬酮、2-癸酮、2,5-己二酮、2,6,8-三甲基-4-壬酮、佛尔酮、二正戊基酮等;或脂肪族醚,例如,戊醚、己醚、二辛醚、乙二醇二丁醚、二乙二醇二乙醚、二乙二醇丁基甲醚、二乙二醇二丁醚、三乙二醇二甲醚、三乙二醇乙基甲醚、三乙二醇丁基甲醚、三丙二醇二甲醚、四乙二醇二甲醚等。
本发明中,所述的油墨组合物进一步包含有另一种有机溶剂。另一种有机溶剂的例子包括(但不限于):甲醇、乙醇、2-甲氧基乙醇、二氯甲烷、三氯甲烷、氯苯、邻二氯苯、四氢呋喃、苯甲醚、吗啉、甲苯、邻二甲苯、间二甲苯、对二甲苯、1,4二氧杂环己烷、丙酮、甲基乙基酮、1,2二氯乙烷、3-苯氧基甲苯、1,1,1-三氯乙烷、1,1,2,2-四氯乙烷、醋酸乙酯、醋酸丁酯、二甲基甲酰胺、二甲基乙酰胺、二甲基亚砜、四氢萘、萘烷、茚和/或它们的混合物。
本发明中,本发明所述的油墨组合物可以是溶液或悬浮液。
本发明所述的油墨组合物可以作为涂料或印刷油墨用于制备有机电子器,特别优选的是通过打印或涂布的制备方法制备电子器件。
其中,适合的打印或涂布技术包括(但不限于)喷墨打印,喷印(NozzlePrinting),活版印刷,丝网印刷,浸涂,旋转涂布,刮刀涂布,辊筒印花,扭转辊印刷,平版印刷,柔版印刷,轮转印刷,喷涂,刷涂或移印,狭缝型挤压式涂布等。首选的是凹版印刷,喷印及喷墨印刷。溶液或悬浮液可以另外包括一个或多个组份例如表面活性化合物,润滑剂,润湿剂,分散剂,疏水剂,粘接剂等,用于调节粘度,成膜性能,提高附着性等。有关打印技术,及其对有关溶液的相关要求,如溶剂及浓度,粘度等,的详细信息请参见Helmut Kipphan主编的《印刷媒体手册:技术和生产方法》(Handbook of Print Media:Technologies andProduction Methods),ISBN 3-540-67326-1。
本发明还提供了一种有机电致发光器件,其中,所述有机电致发光器件的发光层是通过印刷工艺制备得到的;且所述有机电致发光器件的发光层的发光材料包括本发明所述的油墨组合物。
本发明所述的有机电致发光器件可选于,但不限于,有机发光二极管(OLED),有机光伏电池(OPV),有机发光电池(OLEEC),有机场效应管(OFET),有机发光场效应管,有机激光器,有机自旋电子器件,有机传感器及有机等离激元发射二极管(Organic PlasmonEmitting Diode)等,特别是OLED。
本发明中,所述发光材料层中包含本发明所述的油墨组合物和一种磷光发光体,或包含一种所述的油墨组合物和一种主体材料,或包含一种所述的油墨组合物,一种磷光发光体和一种主体材料。
在以上所述的发光器件,特别是OLED中,包括一基片,一阳极,至少一发光层,一阴极。
基片可以是不透明或透明。一个透明的基板可以用来制造一个透明的发光元器件。例如可参见,Bulovic等Nature 1996,380,p29,和Gu等,Appl.Phys.Lett.1996,68,p2606。基片可以是刚性的或弹性的。基片可以是塑料,金属,半导体晶片或玻璃。最好是基片有一个平滑的表面。无表面缺陷的基板是特别理想的选择。在一个优选的实施例中,基片是柔性的,可选于聚合物薄膜或塑料,其玻璃化温度Tg为150℃以上,较好是超过200℃,更好是超过250℃,最好是超过300℃。合适的柔性基板的例子有聚(对苯二甲酸乙二醇酯)(PET)和聚乙二醇(2,6-萘)(PEN)。
阳极可包括一导电金属或金属氧化物,或导电聚合物。阳极可以容易地注入空穴到空穴注入层(HIL)或空穴传输层(HTL)或发光层中。在一个的实施例中,阳极的功函数和发光层中的发光体或作为HIL或HTL或电子阻挡层(EBL)的p型半导体材料的HOMO能级或价带能级的差的绝对值小于0.5eV,较好是小于0.3eV,最好是小于0.2eV。阳极材料的例子包括但不限于:Al、Cu、Au、Ag、Mg、Fe、Co、Ni、Mn、Pd、Pt、ITO、铝掺杂氧化锌(AZO)等。其他合适的阳极材料是已知的,本领域普通技术人员可容易地选择使用。阳极材料可以使用任何合适的技术沉积,如一合适的物理气相沉积法,包括射频磁控溅射,真空热蒸发,电子束(e-beam)等。在某些实施例中,阳极是图案结构化的。图案化的ITO导电基板可在市场上买到,并且可以用来制备根据本发明的器件。
阴极可包括一导电金属或金属氧化物。阴极可以容易地注入电子到EIL或ETL或直接到发光层中。在一个的实施例中,阴极的功函数和发光层中发光体或作为电子注入层(EIL)或电子传输层(ETL)或空穴阻挡层(HBL)的n型半导体材料的LUMO能级或导带能级的差的绝对值小于0.5eV,较好是小于0.3eV,最好是小于0.2eV。原则上,所有可用作OLED的阴极的材料都可能作为本发明器件的阴极材料。阴极材料的例子包括但不限于:Al、Au、Ag、Ca、Ba、Mg、LiF/Al、MgAg合金、BaF2/Al、Cu、Fe、Co、Ni、Mn、Pd、Pt、ITO等。阴极材料可以使用任何合适的技术沉积,如一合适的物理气相沉积法,包括射频磁控溅射,真空热蒸发,电子束(e-beam)等。
OLED还可以包含其他功能层,如空穴注入层(HIL)、空穴传输层(HTL)、电子阻挡层(EBL)、电子注入层(EIL)、电子传输层(ETL)、空穴阻挡层(HBL)。
按照本发明的发光器件,其发光波长在300到1000nm之间,较好的是在350到900nm之间,更好的是在400到800nm之间。
本发明还涉及按照本发明的电致发光器件在各种电子设备中的应用,包含,但不限于,显示设备,照明设备,光源,传感器等等。
本发明提供了一种化合物及其制备方法和应用,实验结果表明,本发明提供的化合物作为有机电致发光器件中的CPL层,能够显著的提高有机电致发光器件的发光效率以及寿命;此外,本发明所述的化合物与高聚物组合得到的油墨组合物易于形成激基络合物,其作为有机电致发光器件的发光层材料时,可以通过印刷工艺实现发光层的涂覆,且得到的发光器件的发光效率和寿命较高。
下面将结合本发明实施例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001的合成
氮气条件下,二苯胺(110mmol),2-溴-9,9-二庚基芴(100mmol),邻菲罗啉(1.98g),碘化亚铜(1.90g),碳酸铯(38.6g,2eq)等物质,溶解在甲苯(300mL)中加热110℃,反应7小时,冷却,常温过滤,除掉金属物质,用旋蒸蒸发溶剂,得到固体001(76mmolg,76%)。
同理,按照上述方法,选择不同的底物得到新的化合物。
实施例2
本发明的有机化合物作为发光器件中的CPL层材料,具有高的Tg(玻璃转化温度),高折射率,对实施例制备的化合物分别进行热性能及折射率的测试,检测结果如表1所示。
表1
实施例3
将本发明所述的式(I)化合物作为CPL层应用于OLED器件的制备,本实施例中的OLED器件为顶发射有机电致发光器件,其结构包括:基板1,和在基板1上依次镀覆形成的反射层2、阳极3、空穴注入层(HIL)4、空穴传输层(HTL)5、发光层(EML)6、电子传输层(ETL)7、电子注入层(EIL)8、阴极9和覆盖层10。
其中,基板1为玻璃基板、石英基板或柔性高分子基板(塑料或聚酰亚胺等);
反射层2可为金属银或银合金,金属铝或铝合金层,用于反射入射基板方向的光线;
阳极层3可为ITO(氧化铟锡)、IZO(氧化铟锌)、高功函数金属或合金、C60等有机半导体材料;均能实现本发明的目的,属于本发明的保护范围。
空穴注入层4选用4,4′,4”-三(N-3-甲基苯基-N-苯基氨基)三苯胺(MTDATA)和2,3,5,6-四氟四氰基奎二甲烷(F4TCNQ)的混合物,两者的质量比例为25∶1。
空穴传输层5为N,N’-二-(1-萘基)-N,N’-二苯基-1,1’-联苯基-4,4’-二胺(NPB)。
发光层6可以是红光、绿光或蓝光。其中,红光的主体RH为Bebq2(双(10-羟基苯并[h]喹啉)铍)、掺杂RD为Ir(piq)2(acac),绿光的主体GH为CBP(4,4′-双(N-咔唑)-1,1′-联苯)、掺杂GD为Ir(ppy)3,蓝光主体BH为ADN、掺杂BD为DPAVB(1,4-二[4-(二甲氨苯基)苯乙烯基]苯);
电子传输层7为Bphen。
电子注入层8可为无机碱金属化合物或有机碱金属配合物。优选碱金属为无机碱金属化合物为LiF,有机碱金属配合物为八羟基喹啉锂。具体制备器件的方法如下:
蓝光器件
基板1为玻璃基板,在基板1上溅射沉积Ag作为反射层2,厚度为150nm,溅射10nm的ITO作为器件的阳极3,并蚀刻出所需的图形,用O3等离子处理3分钟。将所得基板1置于真空中,通过共蒸沉积130nm的MTDATA和F4TCNQ的混合物作为空穴注入层(HIL)4,其中F4TCNQ重量为MTDATA重量的4%。接着沉积10nm的NPB作为空穴传输层(HTL)5。再共蒸沉积30nm的ADN和DPAVB的混合物作为发光层6,其中DPAVB与ADN的摩尔比为1∶20。然后沉积20nm的Bphen作为电子传输层(ETL)7。再蒸镀1nm的LiF作为电子注入层8。阴极9为共同蒸镀K和Ag的合金层10nm,其中K通过KBH4在蒸镀过程中(温度400℃)分解的方式蒸镀,K和Ag摩尔比为8∶1,然后沉积25nm的Ag。蒸镀30nm的本发明化合物001作为CPL层。
绿光器件
与蓝光器件的制备方法一致,只是将HIL的厚度改为170nm,发光层的材料改为CBP和Ir(ppy)3的混合物,其中Ir(ppy)3与CBP的摩尔比1∶10。
红光器件
与蓝光器件的制备方法一致,只是将HIL的厚度改为60nm,发光层的材料改为BeBq2和Ir(piq)2(acac)的混合物,其中Ir(piq)2(acac)与BeBq2的摩尔比为1∶10。
实施例4
具体实施步骤同实施例2,唯一不同的是阴极9为:K和Ag合金层,摩尔比为2∶1,厚度为7nm;Ag层为25nm;CPL层为本发明化合物013,厚度为50nm,制备红光器件。
实施例5
具体实施步骤同实施例2,唯一不同的是阴极9为:Mg和Ag合金层,摩尔比为4∶1,厚度为5nm;Ag层为20nm;CPL层为本发明化合物025,厚度为60nm,制备绿光器件。
实施例6
具体实施步骤同实施例2,唯一不同的是阴极9为:Mg和Ag合金层,摩尔比为6∶1,厚度为7nm;Ag层为25nm;CPL层为本发明化合物037,厚度为30nm,制备红光器件。
实施例7
具体实施步骤同实施例2,唯一不同的是阴极9为:Li和Ag合金层,摩尔比为8∶1,厚度为9nm;Ag层为30nm;CPL层为本发明化合物049,厚度为50nm,制备绿光器件。
实施例8
具体实施步骤同实施例2,唯一不同的是阴极9为:Mg和Ag合金层,摩尔比为4∶1,厚度为11nm;Ag层为20nm;CPL层为本发明化合物061,厚度为45nm,制备蓝光器件。
实施例9~实施例12
具体实施步骤同实施例2,唯一不同的是阴极9为:Mg和Ag合金层,摩尔比为6∶1,厚度为7nm;Ag层为25nm;CPL层为本发明化合物062~065,厚度为30nm,制备红光器件。
实施例13~实施例16
具体实施步骤同实施例2,唯一不同的是阴极9为:Li和Ag合金层,摩尔比为8∶1,厚度为9nm;Ag层为30nm;CPL层为本发明化合物066~069,厚度为50nm,制备绿光器件。
实施例17~实施例19
具体实施步骤同实施例2,唯一不同的是阴极9为:Mg和Ag合金层,摩尔比为4∶1,厚度为11nm;Ag层为20nm;CPL层为本发明化合物070~072,厚度为45nm,制备蓝光器件。
对比例1
本对比例是OLED器件制备实施例,具体步骤如实施例3所述,唯一不同的是所述OLED透明复合阴极9仅包括依次设置的低功函数金属与Ag的合金层、Ag层,不包括CPL层,制备红光器件、绿光器件和蓝光器件。
对比例2
本对比例中OLED器件制备步骤同实施例3,不同的是所述阴极9是一种OLED复合阴极结构,所述OLED复合阴极结构包括依次设置的低功函数金属与Ag的合金层、Ag层。具体步骤如下:在真空条件下,利用热蒸镀技术,蒸镀Mg/Ag合金材料作为所述合金层,Mg/Ag的摩尔比为1∶1,所述合金层的厚度为10nm;在真空条件下,利用热蒸镀技术,在所述所述合金层的上方蒸镀一层Ag层,厚度为10nm,制备红光器件、绿光器件和蓝光器件。
实施例20
对实施例3~19以及对比例1~2得到的OLED器件的性能进行测试,结果见表2。
表2
从上表可以看出,相同类型的器件,实施例中的器件比对比例中的器件的电流效率、亮度寿命更好。
实施例21
印刷OLED器件的制备及测量
OLED器件的结构为ITO/HIL/HTL/EML/ETL/阴极,制备步骤如下:
a、ITO(铟锡氧化物)导电玻璃基片的清洗:使用各种溶剂(例如氯仿、丙酮或异丙醇中的一种或几种)清洗,然后进行紫外臭氧处理;
b、HIL(空穴注入层,60nm):60nm的PEDOT(聚乙撑二氧噻吩,CleviosTMAI4083)作为HIL在超净室旋转涂布而成,并在180℃的热板上处理10分钟;
c、HTL(空穴传输层,20nm):20nm的TFB或PVK(Sigma Aldrich,平均Mn25,000-50,000)是在氮气手套箱中通过旋转涂布而成,所用的溶液是加入至甲苯溶剂的TFB或PVK(SigmaAldrich),溶液溶度5mg/ml,随后在180℃的热板上处理60分钟;
其中,TFB(H.W.SandsCorp.)是一种空穴传输材料,用于HTL,其结构式如下:
d、EML(有机发光层):EML是在氮气手套箱中通过旋转涂布而成,所用的溶液由本发明所述的式(I)化合物、高聚物1~3和甲苯溶剂的石墨烯组合物与金属络合物D组成的混合溶液,其结构式如下所示,溶液溶度10mg/ml,随后在180℃的热板上处理10分钟;表3列出了器件的EML的组分和厚度;
表3
e、阴极:Ba/Al(2nm/100nm)在高真空(1×10-6毫巴)中热蒸镀而成;
f、封装:器件在氮气手套箱中用紫外线固化树脂封装。
各OLED器件的电流电压及发光(IVL)特性通过表征设备来表征,同时记录重要的参数如效率,寿命及驱动电压,OLED器件的性能结果见表4。
表4
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 (9)
3.一种化合物作为CPL层在制备有机电致发光器件中的应用,所述化合物具有式(I)所示结构,
其中,
所述Ar1选自氢、甲基、乙基、丙基、正丁基、叔丁基、戊基、三氟甲基、苯基、蒽基、萘基、菲基、3-叔丁基苯基、3-三氟甲基苯基、3-正丙基苯基、3-异丙基苯基、3-甲基苯基、4-叔丁基苯基、4-三氟甲基苯基、4-正丙基苯基、4-异丙基苯基、4-甲基苯基、3,5-二甲基苯基、2-噻吩基、吡啶基、哒嗪基、吡嗪基、三嗪基或吖啶基;
所述Ar2选自氢、甲基、乙基、丙基、正丁基、叔丁基、戊基、三氟甲基、苯基、蒽基、萘基、菲基、3-叔丁基苯基、3-三氟甲基苯基、3-正丙基苯基、3-异丙基苯基、3-甲基苯基、4-叔丁基苯基、4-三氟甲基苯基、4-正丙基苯基、4-异丙基苯基、4-甲基苯基、3,5-二甲基苯基、2-噻吩基、吡啶基、哒嗪基、吡嗪基、三嗪基或吖啶基;
所述X1-a、X1-b、X1-c、X1-d、X1-e独立的选自氮或碳;
所述X2-a、X2-b、X2-c、X2-d、X2-e独立的选自氮或碳;
所述R1、R2独立的选自C5~C9的烷基。
4.根据权利要求1~3任一项所述的应用,其特征在于,所述X1-a、X1-b、X1-c、X1-d、X1-e中至多有3个为氮;
所述X2-a、X2-b、X2-c、X2-d、X2-e中至多有3个为氮。
5.根据权利要求1~3任一项所述的应用,其特征在于,所述R1、R2独立的选自正戊基、正己基、正庚基、正辛基或正癸基。
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