CN110066227A - 有机电致发光材料及发光器件 - Google Patents
有机电致发光材料及发光器件 Download PDFInfo
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- CN110066227A CN110066227A CN201810068377.9A CN201810068377A CN110066227A CN 110066227 A CN110066227 A CN 110066227A CN 201810068377 A CN201810068377 A CN 201810068377A CN 110066227 A CN110066227 A CN 110066227A
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- 239000011368 organic material Substances 0.000 title claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 125000001424 substituent group Chemical group 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims abstract 2
- 239000010410 layer Substances 0.000 claims description 35
- 238000005401 electroluminescence Methods 0.000 claims description 19
- 239000012044 organic layer Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000000975 dye Substances 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- 230000005611 electricity Effects 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 description 41
- 238000003786 synthesis reaction Methods 0.000 description 41
- 239000000463 material Substances 0.000 description 31
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 238000001819 mass spectrum Methods 0.000 description 13
- 239000000376 reactant Substances 0.000 description 13
- 230000005540 biological transmission Effects 0.000 description 8
- 238000010189 synthetic method Methods 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- OYFFSPILVQLRQA-UHFFFAOYSA-N 3,6-ditert-butyl-9h-carbazole Chemical compound C1=C(C(C)(C)C)C=C2C3=CC(C(C)(C)C)=CC=C3NC2=C1 OYFFSPILVQLRQA-UHFFFAOYSA-N 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 230000027756 respiratory electron transport chain Effects 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 238000007738 vacuum evaporation Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000006575 electron-withdrawing group Chemical group 0.000 description 3
- 238000007306 functionalization reaction Methods 0.000 description 3
- 230000005283 ground state Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- CEBAHYWORUOILU-UHFFFAOYSA-N (4-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=C(C#N)C=C1 CEBAHYWORUOILU-UHFFFAOYSA-N 0.000 description 2
- -1 1,3- dibromo phenyl Chemical group 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CGDKALWGXBQBHQ-UHFFFAOYSA-N CC=1C(=O)CC(CC1C)(C)C.N#CC#N.N#CC#N Chemical compound CC=1C(=O)CC(CC1C)(C)C.N#CC#N.N#CC#N CGDKALWGXBQBHQ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 238000007747 plating Methods 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 239000012925 reference material Substances 0.000 description 2
- 238000009877 rendering Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000007740 vapor deposition Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NPLZNDDFVCGRAG-UHFFFAOYSA-N (2-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1C#N NPLZNDDFVCGRAG-UHFFFAOYSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 239000011162 core material Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- ZEWMZYKTKNUFEF-UHFFFAOYSA-N indium;oxozinc Chemical compound [In].[Zn]=O ZEWMZYKTKNUFEF-UHFFFAOYSA-N 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 150000002739 metals Chemical group 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 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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- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
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- C07—ORGANIC CHEMISTRY
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- 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
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- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems 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 carbon atoms of the ring system
- C07D219/06—Oxygen atoms
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- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/38—[b, e]-condensed with two six-membered rings
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- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
- C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
- C07D279/18—[b, e]-condensed with two six-membered rings
- C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom
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- 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
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Abstract
一种有机电致发光材料,其为下述通式(1)所示的化合物,其中Ar2氰基取代苯基,Ar1为给电子基团,独立地选自取代或未取代的C6~C60的芳烃基、取代或未取代的C3~C60的杂芳烃基,这些基团可以具有取代基;m为2~4的整数,m个Ar1可以相同也可以不同,氰基取代苯基的氰基可以位于苯环的任意位置,优选位于邻位或对位。
Description
技术领域
本发明涉及一种有机化合物,其可以用作有机电致发光器件的发光材料;本发明还涉及该化合物在有机电致发光器件中的应用及有机电致发光器件。
背景技术
有机电致发光材料的有机电致发光器件(OLED),可以用于固体发光型的全色彩显示以及固态白光照明等领域,被誉为下一代新型显示及照明技术。通常OLED器件含有发光层和夹持该层的一对对置电极。器件在两电极间施加电场时,从阴极侧注入电子,从阳极侧注入空穴,电子在发光层中与空穴复合,形成激发状态,激发状态恢复到基态时,能量以光的形式放出。随着OLED技术在照明和显示两大领域的不断推进,人们对于其核心材料的研究更加关注,一个效率好寿命长的有机电致发光器件通常是器件结构以及各种有机材料的优化搭配的结果,这就为化学家们设计开发各种结构的功能化材料提供了极大的机遇和挑战。常见的功能化有机材料有:空穴注入材料、空穴传输材料、空穴阻挡材料、电子注入材料、电子传输材料,电子阻挡材料以及发光主体材料和发光客体(染料)等。为了制备性能更好的发光器件,业界一直致力于开发新的有机电致发光材料以进一步提高器件的发光效率和寿命。
众所周知,效率优异的蓝光发光材料一直是业界开发的重点。在WO2015080183A1专利文献中,公开了一类双氰基与苯分子相连的有机电致发光材料,但是这类发光材料中带氰基的吸电子基团苯与给电子基团R直接相连,这会造成材料带隙不够宽,不利于蓝光发光材料的构建。
在WO2017190885A1,WO2016181846A1,DE102016108335B3专利文献中,也公开了类似的双氰基与苯分子有机电致发光材料,但是这些专利文献中公开的化合物在蓝光发光效率方面还不是很理想。现有的功能化有机材料在蓝光发光性能方面还有很大改进余地,业界亟需开发新的有机电致发光材料,尤其是蓝色发光的有机电致发光材料。
发明内容
本发明的发明人经过锐意研究,发现将下述通式(1)所示的化合物用作有机电致发光材料时,可以在器件中很好的实现蓝光的发光,而且有着良好的发光效率,从而完成了本发明。通式(1)所示的化合物具体为:
其中Ar2为下述通式(2)表示的基团:
*代表与苯环的连接位点,
Ar1为给电子基团,独立地选自取代或未取代的C6~C60的芳烃基、取代或未取代的C3~C60的杂芳烃基,这些基团可以具有取代基;m为2~4的整数,m个Ar1可以相同也可以不同。
本发明的化合物能够实现良好的蓝光发光效率的原因并不明确,分析可能是因为通过在带氰基的吸电子基团苯(即通式(2)的基团)(与给电子基团Ar1之间间隔1个苯,并引入大位阻给电子基团Ar2,使得材料带隙更宽,增大了位阻作用,这有利于减少振动弛豫,抑制分子内转动,可以使发光光谱变窄,蓝色发光显色性更好。
本发明中的m优选为3、4,更优选为4。也就是说,优选Ar1尽可能的多,这样的结果是能够进一步的增大了位阻作用,这有利于分子中心部分的电子云相对更加稳定,从而提高了载流子的传输效率,因而,能够表现为有机发光器件的高效率。
Ar1为给电子基团,独立地选自取代或未取代的C6~C60的芳烃基、取代或未取代的C3~C60的杂芳烃基,这些基团可以具有取代基;m为2~4的整数,m个Ar1可以相同也可以不同,
氰基取代苯基的氰基可以位于苯环的任意位置,优选位于邻位或对位,更优选为对位。当位于对位时,该化合物能实现的蓝色发光效果更好,其机理尚不明确,但是众所周知氰基在对位有着最强的拉电子效应,推测这可能是使蓝色发光发色性能更佳的原因。
式(2)基团在式(1)中的取代位置,可以为邻位、间位、对位。
作为上述Ar1的给电子基团,从更好的蓝色发光显色性方面考虑,优选为下述基团,
其中的R独立地选自取代或未取代的C1~C20的脂肪烃基、取代或未取代的C6~C30的芳香烃基、取代或未取代的C5~C30的杂芳香烃基,取代或未取代的C1~C30的含硅的烷基,取代或未取代的C1~C30的含硼的烷基,n为0~10的整数;*代表与苯环的连接位置,R基团的取代位置表示可以在Ar1基团上可取代的任意位置。
Ar1的给电子集团,进一步优选下述基团,
这些基团能够提供足够的给电子特性,而且空间位阻也更合适,且原料容易获得。
作为上述的R取代基,R优选选自以下取代基,
通过引入上述取代基,本发明的化合物用于电致发光器件时的发光效率进一步提高,其原因并不清楚。可能的原因是,由于涉及三线态激子的一般来说都是Dexter能量传递,Dexter能量传递是以载流子直接交换的方式传递能量,当一个处于激发态的分子和另外一个处于基态的分子离的很近,以至于电子云彼此交叠的时候,处于激发态的分子上的电子和空穴就能直接迁移到处于基态的临近分子上,在完成载流子迁移的同时完成能量的转移。显然,对于Dexter能量转移,由于需要电子云的交叠,因此只能在紧邻的分子之间才能完成,本发明化合物通过引入大位阻基团,有效的避免了电子云交叠,导致dexter能量传递受限,能量通过辐射跃途径发光从而有效提高发光效率。
作为本发明中的具体化合物,可例举以下的P1~P69,但本发明的范围不受这些化合物的限制。
针对上述现有技术方案,本发明通过在带氰基的吸电子基团苯与给电子基团R之间间隔1个苯,使得更有利于蓝光的发光,并引入大位阻给电子基团R,使得材料带隙更宽,增大了位阻作用,这有利于减少振动弛豫,抑制分子内转动,窄化光谱,改善了发光效率。
需要说明的是,本发明中,Ca~Cb的表达方式代表该基团具有的碳原子数为a~b,除非特殊说明,一般而言该碳原子数不包括取代基的碳原子数。
本发明中,对于化学元素的表述包含化学性质相同的同位素的概念,例如“氢”的表述,也包括化学性质相同的“氘”、“氚”的概念。
本发明中的杂原子,通常指选自B、N、O、S、P、P(=O)、Si和Se中的原子或原子团。
本发明还涉及上述化合物在有机电致发光器件中作为发光层材料的应用,进而作为主体材料的应用。需要说明的是,所述通式(1)中的化合物可以但不限于在有机电致发光器件中用作发光层材料。
本发明提供一种有机电致发光器件,包括位于基板上的第一电极和第二电极,以及位于电极之间有机层,所述有机层至少包括空穴传输层、发光层、电子传输层,其特征在于,所述有机层包含上述化合物。
本发明的化合物作为蓝光染料使用时,发色性能优异,且发光效率优良,能够适用于高效的有机电致发光器件。
具体实施方式
上述通式(I)中的化合物可以但不限于在有机电致发光器件中用作发光层材料。
下面将以多个合成实施例为例来详述本发明的化合物的具体制备方法,但本发明的制备方法并不限于这多个合成实施例,本领域技术人员可以在其基础上在不悖离本发明原则的前提下进行任何修改、等同替换、改进等,而将该方法扩展到本发明的权利要求书要求保护的技术方案的范围之内。
合成实施例
代表性合成路径1:
代表性合成路径2:
更具体地,以下给出本发明的代表性中间体为式(M1)~(M5)的合成方法。
中间体(M1)~(M5)的结构如下:
合成例1:中间体M1的合成
在氮气氛围下,将0.11mol 1,4-二溴四氟苯,0.1mol 4-氰基苯硼酸,0.001molPd2(dba)3,0.002mol s-phos,0.2molK3PO4溶解到300ml甲苯和100ml水的混合溶液中,100℃反应12h。用色谱柱分离。得M1,质谱:352。
合成例2:中间体M2的合成
将反应物1,4-二溴四氟苯替换为1,3-二溴四氟苯,经过与合成例1相同的合成方法,得M2,质谱:352。
合成例3:中间体M3的合成
将反应物1,4-二溴四氟苯替换为1,2-二溴四氟苯,经过与合成例1相同的合成方法,得M3,质谱:352。
合成例4:中间体M4的合成
将反应物4-氰基苯硼酸替换为2-氰基苯硼酸,经过与合成例1相同的合成方法,得M4,质谱:352。
合成例5:中间体M5的合成
将反应物1,4-二溴四氟苯替换为1,4-二溴-2,5-二氟苯,经过与合成例1相同的合成方法,得M5,质谱:316。
合成例6:P1的合成
在氮气氛围下,将0.02mol M1,0.08mol 3,6-二叔丁基咔唑,0.04mol K3PO4溶解到200ml DMSO溶液中,120℃反应12h。用色谱柱分离。得P1,质谱:1389。
合成例7:P3的合成
将反应物M1替换为M2,经过与合成例6相同的合成方法,得P3,质谱:1389。
合成例8:P5的合成
将反应物M1替换为M3,经过与合成例6相同的合成方法,得P5,质谱:1389。
合成例9:P11的合成
将反应物M1替换为M4,经过与合成例6相同的合成方法,得P11,质谱:1389。
合成例10:P13的合成
将反应物3,6-二叔丁基咔唑替换为吩噁嗪,经过与合成例6相同的合成方法,得P13,质谱:1004。
合成例11:P21的合成
将反应物3,6-二叔丁基咔唑替换为3,6-二叔丁基咔啉,经过与合成例6相同的合成方法,得P21,质谱:1393。
合成例12:P25的合成
将反应物M1替换为M5,将反应物3,6-二叔丁基咔唑替换为3,6-双(环丙基二甲基甲硅烷基)-咔唑,经过与合成例6相同的合成方法,得P25,质谱:1002。
合成例13:P48的合成
将反应物M1替换为M5,将反应物3,6-二叔丁基咔唑替换为3,6-双(二甲基硼基)-咔唑,经过与合成例6相同的合成方法,得P48,质谱:770。
器件实施例
有机发光二极管包括位于基板上的阳极和阴极,以及位于电极之间有机材料,阳极以上依次为空穴传输层、发光层、电子传输层。
基板使用有机发光显示器所用的基板,例如:玻璃、聚合物材料以及带有TFT元器件的玻璃和聚合物材料等。
阳极材料可以采用铟锡氧(ITO)、铟锌氧(IZO)、二氧化锡(SnO2)、氧化锌(ZnO)等透明导电材料,也可以是银及其合金、铝及其合金等金属材料,也可以是PEDOT等有机导电材料,及上述材料的多层结构。
阴极为镁银混合物、LiF/Al、ITO等金属、金属混合物、氧化物
空穴传输层选自但不限于以下所罗列的HT1-HT31一种或多种化合物的组合
其中,蓝色荧光主体选自但不限于以下所罗列的TDH1-TDH20一种或多种化合物的组合
电子传输层选自但不限于以下所罗列的ET1-ET57一种或多种化合物的组合
器件中还可以包括但不限于位于空穴传输层与发光层之间的空穴注入层,选自以下所罗列的HT1-HT14一种或多种化合物的组合,
器件中还可以包括但不限于电子传输层与阴极之间的电子注入层,电子注入层材料包括但不限于以下罗列的一种或多种的组合。
LiQ,LiF,NaCl,CsF,Li2O,Cs2CO3,BaO,Na,Li,Ca
本实施例中还用到的材料如下:
本实施例中有机电致发光器件制备过程如下:
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HT11作为空穴注入层,蒸镀速率为0.1nm/s,蒸镀膜厚为10nm;
在空穴注入层之上真空蒸镀HT-2作为器件的空穴传输层,蒸镀速率为0.1nm/s,蒸镀总膜厚为80nm;
在空穴传输层之上真空蒸镀器件的发光层,发光层包括主体材料和染料材料,利用多源共蒸的方法,调节主体材料TDH-2蒸镀速率为0.1nm/s,本发明的化合物蒸镀速率3%比例设定,蒸镀总膜厚为30nm;
在发光层之上真空蒸镀器件的电子传输层材料ET-56,其蒸镀速率为0.1nm/s,蒸镀总膜厚为30nm;
在电子传输层(ETL)上真空蒸镀厚度为0.5nm的LiF作为电子注入层,厚度为150nm的Al层作为器件的阴极。
由此制备了蓝色发光的有机电致发光器件,使用PR655光谱仪对该器件的驱动电压电流效率和EL进行了以下的测试,结果见下表:
有机电致发光器件性能见下表:
化合物编号 | 要求亮度cd/m<sup>2</sup> | 电压V | 电流效率cd/A | 发射光谱nm |
参比材料P70 | 1000.00 | 5.7 | 10.9 | 460 |
参比材料P71 | 1000.00 | 6.2 | 15.6 | 474 |
化合物P1 | 1000.00 | 5.2 | 25.1 | 454 |
化合物P3 | 1000.00 | 5.1 | 24.6 | 456 |
化合物P5 | 1000.00 | 5.2 | 23.7 | 452 |
化合物P11 | 1000.00 | 5.3 | 23.1 | 463 |
化合物P13 | 1000.00 | 5.0 | 20.5 | 458 |
化合物P21 | 1000.00 | 5.1 | 24.4 | 460 |
化合物P25 | 1000.00 | 5.4 | 20.8 | 459 |
化合物P48 | 1000.00 | 5.3 | 22.5 | 457 |
本发明的化合物与外围没有取代基的P70相比,发光光谱基本一致,都能实现非常良好的蓝光发光,但发光的效率大大提高了。与P71相比,本发明实现了更纯正的蓝色发光,这在有机电致发光领域是非常难得的,对于扩展发光器件的色域、改善显示效果有着非常重要的意义,同时,本发明的发光效率也略有提高。
以上结果表明,本发明的新型有机材料用于有机电致发光器件,可以有效的降低驱动电压,提高电流效率,是性能良好的蓝色发光材料。
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 (10)
1.一种有机电致发光材料,其为下述通式(1)所示的化合物,
其中Ar2为下述通式(2)表示的基团:
*代表与苯环的连接位点,
Ar1为给电子基团,独立地选自取代或未取代的C6~C60的芳烃基、取代或未取代的C3~C60的杂芳烃基,这些基团可以具有取代基;m为2~4的整数,m个Ar1可以相同也可以不同。
2.根据权利要求1所述的有机电致发光材料,其中,Ar1选自以下基团,
R独立地选自取代或未取代的C1~C20的脂肪烃基、取代或未取代的C6~C30的芳香烃基、取代或未取代的C3~C30的杂芳香烃基,取代或未取代的C1~C30的含硅的烷基,取代或未取代的C1~C30的含硼的烷基,n为0~10的整数;
*代表与苯环的连接位置,R基团的取代位置表示可以在Ar1基团上可取代的任意位置。
3.根据权利要求2所述的有机电致发光材料,其中,R分别独立地选自以下取代基,
4.根据权利要求1所述的有机电致发光材料,其中,通式(1)中,两个Ar2位于苯环的对位,通式(2)中,氰基取代在苯环的对位。
5.根据权利要求4所述的有机电致发光材料,其中,n=4。
6.根据权利要求1所述的有机电致发光材料,其中通式1表示的化合物选自下述化合物P1~P69:
7.权利要求1~6中任一项所述的有机化合物在有机电致发光器件中的应用。
8.一种有机电致发光器件,包括第一电极、第二电极和插入在所述第一电极和第二电极之间的多个有机层,其特征在于,所述有机层中含有权利要求1~6中任一项所述的有机化合物。
9.根据权利要求8所述有机电致发光器件,其中,权利要求1~6中任一项所述的有机化合物在发光层中用作染料。
10.根据权利要求9所述有机电致发光器件,其中,所述发光层为蓝光的发光层。
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CN112409240A (zh) * | 2020-11-20 | 2021-02-26 | 清华大学 | 一种有机化合物及其应用及采用该化合物的有机电致发光器 |
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