CN114105868B - 一种以4-氰基吡啶为核心的有机化合物及包含其的有机电致发光器件 - Google Patents
一种以4-氰基吡啶为核心的有机化合物及包含其的有机电致发光器件 Download PDFInfo
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- CN114105868B CN114105868B CN202010903321.8A CN202010903321A CN114105868B CN 114105868 B CN114105868 B CN 114105868B CN 202010903321 A CN202010903321 A CN 202010903321A CN 114105868 B CN114105868 B CN 114105868B
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- cyanopyridine
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 25
- GPHQHTOMRSGBNZ-UHFFFAOYSA-N pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC=C1 GPHQHTOMRSGBNZ-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 239000000463 material Substances 0.000 claims abstract description 55
- 239000010410 layer Substances 0.000 claims description 49
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 12
- 229910052805 deuterium Inorganic materials 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 239000002346 layers by function Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000002019 doping agent Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 12
- 230000000694 effects Effects 0.000 abstract description 5
- 230000003595 spectral effect Effects 0.000 abstract description 4
- 239000004065 semiconductor Substances 0.000 abstract description 3
- -1 anthracyl Chemical group 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 9
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 125000001072 heteroaryl group Chemical group 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000002994 raw material Substances 0.000 description 7
- 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 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000001624 naphthyl group Chemical group 0.000 description 6
- 125000005561 phenanthryl group Chemical group 0.000 description 6
- 125000004076 pyridyl group Chemical group 0.000 description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 229910052722 tritium Inorganic materials 0.000 description 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 5
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 5
- 125000002541 furyl group Chemical group 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 5
- 125000001544 thienyl group Chemical group 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 4
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 description 4
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000002883 imidazolyl group Chemical group 0.000 description 4
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 4
- 238000004020 luminiscence type Methods 0.000 description 4
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 4
- 125000002971 oxazolyl group Chemical group 0.000 description 4
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 125000003373 pyrazinyl group Chemical group 0.000 description 4
- 125000002098 pyridazinyl group Chemical group 0.000 description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 description 4
- 238000006862 quantum yield reaction Methods 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 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 3
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QEBYEVQKHRUYPE-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(1-methylpyrazol-3-yl)methyl]-4-[[methyl(pyridin-3-ylmethyl)amino]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CN(C)N=C1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CN=C1 QEBYEVQKHRUYPE-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
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- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
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- 239000000243 solution Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
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- 239000011593 sulfur Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000003996 delayed luminescence Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000011982 device technology Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
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- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
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- 239000012044 organic layer Substances 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
- 239000010970 precious metal Substances 0.000 description 1
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- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
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Classifications
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- 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
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Abstract
本发明涉及一种以4‑氰基吡啶为核心的有机化合物及包含其的有机电致发光器件,属于半导体技术领域,本发明提供化合物的结构如通式(1)所示,本发明还公开了包含上述化合物的有机电致发光器件。本发明提供的化合物具有较高的热稳定性,作为OLED发光器件的发光层材料使用时,可产生TADF效果,具有较高的PLQY且光谱变化较小,可有效提升OLED器件的光电性能以及OLED器件的寿命。
Description
技术领域
本发明涉及半导体技术领域,尤其涉及一种以4-氰基吡啶为核心的有机化合物及包含其的有机电致发光器件。
背景技术
有机电致发光(OLED:Organic Light Emission Diodes)器件技术既可以用来制造新型显示产品,也可以用于制作新型照明产品,有望替代现有的液晶显示和荧光灯照明,应用前景十分广泛。OLED发光器件犹如三明治的结构,包括电极材料膜层,以及夹在不同电极膜层之间的有机功能材料,各种不同功能材料根据用途相互叠加在一起共同组成OLED发光器件。作为电流器件,当对OLED发光器件的两端电极施加电压,并通过电场作用有机层功能材料膜层中的正负电荷,正负电荷进一步在发光层中复合,即产生OLED电致发光。
OLED的发光层材料的开发及使用前后共经历了三个主要阶段,第一阶段以荧光发光机制为主,第二阶段以磷光发光机制为主,第三阶段运用TADF材料作为发光层材料,有效的利用三线态激子从而提升器件的发光效率。TADF材料发展至今,在发光层中有丰富的应用,且其结构可控,性质稳定,价格便宜无需贵重金属,在OLEDs领域的应用前景广阔。
理论上,TADF材料可以通过三线态到单线态的反系间窜跃,实现100%的激子利用率,但在实际应用充当主体或者掺杂的过程中,器件效果不佳,其主要仍然存在如下问题:(1)由于TADF材料设计要求较小的S1-T1带隙,快速的反系间窜跃速率(较短的延迟发光寿命)与高荧光量子产率难以兼得;(2)由于较强的CT效应,TADF材料存在随比例不同而导致的光谱不稳定现象。
氰基修饰的化合物在有机电致发光材料领域可以被用于发光层掺杂材料,比如Wei Huang等人报道了一种TADF掺杂剂(4CzCNPy),可以实现绿色发光,发射峰在524nm,并且可以达到10%以上的EQE(DOI:10.1002/adom.201500016);CN110914378A公开了一种以氰基苯为核心的化合物,使用该类化合物制备的OLED能够达到高激发态而不产生快速的劣化,然而以上公开材料制备的OLED器件存在荧光量子产率低缺点。
发明内容
针对现有技术存在的上述问题,本发明申请人提供了一种有机化合物。本发明的化合物具有窄半峰宽、高荧光量子产率,具有高的玻璃化转变温度和分子热稳定性,以及具有合适的HOMO和LUMO能级,可用作有机电致发光器件的发光层掺杂材料,从而提升器件的发光色纯度和寿命。
本发明提供具体技术方案如下:一种以4-氰基吡啶为核心的有机化合物,所述有机化合物的结构如通式(1)所示:
其中R1、R2分别独立的表示为通式(2)、通式(3)或通式(4)所示结构;且至少有一个表示为通式(3)所示结构,至少有一个表示为通式(2)或通式(4)所示结构;
通式(2)~通式(4)中,Z1每次出现分别独立地表示为C、N或者C-R3;
Z2每次出现分别独立地表示为C、N或者C-R4;
Z3每次出现分别独立地表示为C、N或者C-R5;
*标表示与通式(1)的连接位点;
R3、R4、R5每次出现分别独立的表示为氢、氘、取代或未取代的C1~C10烷基、取代或未取代的C1~C10烷氧基、取代或未取代的氨基、取代或未取代的C6~C30芳基、取代或未取代的C6~C30芳氧基、取代或未取代的C2~C30杂芳基;相邻的R3、R4或R5可以相互连接成环;
X表示为-O-,-S-,-CRaRb-;Ra、Rb分别独立的表示为取代或未取代的C1~C10烷基、取代或未取代的氨基、取代或未取代的C6~C30芳基、取代或未取代的C6~C30芳氧基或取代或未取代的C2~C30杂芳基;
通式(4)与通式(1)相连处的Z3表示为C;
取代上述可取代基团的取代基任选自氘、氚、氰基、卤素、C1~C10烷基、C3~C10环烷基、C6~C30芳基、C2~C30杂芳基中的任意一种;
所述杂芳基和杂环中的杂原子任选自氧、硫或氮中的一种或多种。
进一步,所述有机化合物结构如通式(1-1)或通式(1-2)所示:
通式(1-1)和通式(1-2)中,Z1每次出现分别独立地表示为C、N或者C-R3;
R1、R2分别独立的表示为通式(2)或通式(4)所示结构;
通式(2)和通式(4)中,
Z2每次出现分别独立地表示为C、N或者C-R4;
Z3每次出现分别独立地表示为C、N或者C-R5;
*标表示与通式(1)的连接位点;
R3、R4、R5每次出现分别独立的表示为氢、氘、取代或未取代的C1~C10烷基、取代或未取代的C1~C10烷氧基、取代或未取代的氨基、取代或未取代的C6~C30芳基、取代或未取代的C6~C30芳氧基、取代或未取代的C2~C30杂芳基;相邻的R3、R4或R5可以相互连接成环;
X表示为-O-,-S-,-CRaRb-;Ra、Rb分别独立的表示为取代或未取代的C1~C10烷基、取代或未取代的氨基、取代或未取代的C6~C30芳基、取代或未取代的C6~C30芳氧基或取代或未取代的C2~C30杂芳基;
取代上述可取代基团的取代基任选自氘、氚、氰基、卤素、C1~C10烷基、C3~C10环烷基、C6~C30芳基、C2~C30杂芳基中的任意一种;
所述杂芳基和杂环中的杂原子任选自氧、硫或氮中的一种或多种。
进一步,所述通式(2)表示为取代或未取代的以下基团的任一种:
上述基团的取代基任选自氘、氚、氰基、氟原子、甲基、乙基、叔丁基、异丙基、丁烷基、金刚烷基、2,2-二甲基丁烷、3,3-二甲基戊烷、环己烷基、苯基、萘基、二联苯基、三联苯基、菲基、蒽基、二苯基氨基、9,9-二甲基芴基、9,9-二苯基芴基、螺芴基、吡啶基、咔唑基、呋喃基、嘧啶基、吡嗪基、哒嗪基、噻吩基、二苯并呋喃基、二苯并噻吩基、N-苯基咔唑基、喹啉基、异喹啉基、萘啶基、恶唑基、咪唑基、苯并恶唑基、苯并咪唑基、吩噁嗪基、吩噻嗪基。
进一步,所述通式(3)表示为取代或未取代的以下基团的任一种:
上述基团的取代基任选自氘、氚、氰基、氟原子、甲基、乙基、叔丁基、异丙基、丁烷基、金刚烷基、2,2-二甲基丁烷、3,3-二甲基戊烷、环己烷基、苯基、萘基、二联苯基、三联苯基、菲基、蒽基、二苯基氨基、9,9-二甲基芴基、9,9-二苯基芴基、螺芴基、吡啶基、咔唑基、呋喃基、嘧啶基、吡嗪基、哒嗪基、噻吩基、二苯并呋喃基、二苯并噻吩基、N-苯基咔唑基、喹啉基、异喹啉基、萘啶基、恶唑基、咪唑基、苯并恶唑基、苯并咪唑基、吩噁嗪基、吩噻嗪基。
进一步,所述通式(4)表示为取代或未取代的以下基团的任一种:
上述基团的取代基任选自氘、氚、氰基、氟原子、甲基、乙基、叔丁基、异丙基、丁烷基、金刚烷基、2,2-二甲基丁烷、3,3-二甲基戊烷、环己烷基、苯基、萘基、二联苯基、三联苯基、菲基、蒽基、二苯基氨基、9,9-二甲基芴基、9,9-二苯基芴基、螺芴基、吡啶基、咔唑基、呋喃基、嘧啶基、吡嗪基、哒嗪基、噻吩基、二苯并呋喃基、二苯并噻吩基、N-苯基咔唑基、喹啉基、异喹啉基、萘啶基、恶唑基、咪唑基、苯并恶唑基、苯并咪唑基、吩噁嗪基、吩噻嗪基。
进一步,R每次出现相同或不同的表示为氢、氘、取代或未取代的甲基、取代或未取代的叔丁基、取代或未取代的异丙基、取代或未取代的环己烷基、取代或未取代的甲氧基、取代或未取代的乙氧基、取代或未取代的苯基、取代或未取代的二联苯基、取代或未取代的三联苯基、取代或未取代的萘基、取代或未取代的蒽基、取代或未取代的菲基、取代或未取代的二苯基氨基、取代或未取代的吡啶基、取代或未取代的喹啉基、取代或未取代的呋喃基、取代或未取代的噻吩基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的咔唑基、取代或未取代的N-苯基咔唑基、取代或未取代的9,9-二甲基芴基、取代或未取代9,9-二苯基芴基、取代或未取代的螺芴基、取代或未取代的吩噁嗪基、取代或未取代的吩噻嗪基、取代或未取代的萉基、取代或未取代的吲哚并咔唑、取代或未取代的苯并萘并呋喃基、取代或未取代的苯并呋喃并二苯并呋喃基;相邻的R可以相互连接成环;
Ra、Rb分别独立的表示为取代或未取代的甲基、取代或未取代的叔丁基、取代或未取代的异丙基、取代或未取代的环己烷基、取代或未取代的苯基、取代或未取代的二联苯基、取代或未取代的三联苯基、取代或未取代的萘基、取代或未取代的蒽基、取代或未取代的菲基、取代或未取代的二苯基氨基、取代或未取代的吡啶基、取代或未取代的喹啉基、取代或未取代的二苯并呋喃基、取代或未取代的二苯并噻吩基、取代或未取代的咔唑基、取代或未取代的N-苯基咔唑基、取代或未取代的9,9-二甲基芴基、取代或未取代9,9-二苯基芴基、取代或未取代的螺芴基;
取代上述可取代基团的取代基任选自氘、氚、氰基、氟原子、甲基、乙基、叔丁基、异丙基、丁烷基、金刚烷基、2,2-二甲基丁烷、3,3-二甲基戊烷、环己烷基、苯基、萘基、二联苯基、三联苯基、菲基、蒽基、二苯基氨基、9,9-二甲基芴基、9,9-二苯基芴基、螺芴基、吡啶基、咔唑基、呋喃基、嘧啶基、吡嗪基、哒嗪基、噻吩基、二苯并呋喃基、二苯并噻吩基、N-苯基咔唑基、喹啉基、异喹啉基、萘啶基、恶唑基、咪唑基、苯并恶唑基、苯并咪唑基、吩噁嗪基、吩噻嗪基。
进一步,所述有机化合物的具体结构式为以下结构中的任一种:
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一种有机发光器件,包含阴极、阳极和功能层,所述功能层位于阴极和阳极之间,所述有机发光器件的功能层中所述以4-氰基吡啶为核心的有机化合物。
进一步,所述的有机发光器件的功能层包含发光层,所述发光层含有所述以4-氰基吡啶为核心的有机化合物。
进一步,所述发光层包含第一主体材料、第二主体材料和掺杂材料,所述第一主体材料和第二主体材料中至少有一个为TADF材料,且至少有一个为所述以4-氰基吡啶为核心的有机化合物。
TADF敏化荧光技术(TSF)将TADF材料与荧光掺杂材料相结合,利用TADF材料作为激子敏化媒介,将电激发形成的三线态激子转变为单线态激子,通过单线态激子长程能量传递将能量传递给荧光掺杂材料,同样可以达到100%的器件内量子效率,该技术能弥补荧光掺杂材料激子利用率不足的缺点,有效发挥荧光掺杂材料高荧光量子产率、高器件稳定性、高色纯度及价廉的特点,在OLEDs应用上具有广阔前景。
与现有技术相比,本发明有益的技术效果在于:
(1)具有较高的热稳定性,以及膜相态稳定性,从而使得材料作为器件是具有较强的稳定性,从而有效的提升器件的寿命。
(2)具有高效的TADF特性,使得本发明材料作为主体材料时能充分的利用三线态能量提升器件的发光效率
(3)具有较短的延迟寿命,三线态激子存在时间短,有效减小主体材料的三线态激子猝灭,延长器件的寿命。
(4)具有较好的光谱稳定性,本发明材料作为敏化剂时,可以确保能量有效传递到掺杂材料;
(5)具有较高的PLQY,本发明材料作为敏化剂时,可以有效提升器件的效率。
附图说明
图1为本发明所列举的材料应用于OLED器件的结构示意图;
其中,1为透明基板层,2为阳极层,3为空穴注入层,4为空穴传输层,5为电子阻挡层,6为发光层,7为空穴阻挡,8为电子传输层,9为电子注入层,10为阴极层。
具体实施方式
本发明合成实施例中涉及到的原料均采购于中节能万润有限公司。
实施例1:化合物1的合成
(1)将原料1-1(1.7mmol),原料1-2(4.2mmol)、K2CO3(17mmol),DMSO(10ml)加入到三口瓶中,在150℃下加热回流12h。冷却至室温倒入200ml水中析出大量固体搅拌0.5h,抽滤得白色固体,柱层析提纯,收率88.5%,得到中间体1-1。
(2)在氮气气氛下,向三口烧瓶中加入0.01mol中间体1-1、0.025mol原料1-3、0.03mol叔丁醇钠、5×10-5mol Pd2(dba)3和5×10-5mol三叔丁基磷,然后加入150ml甲苯将其溶解,加热至100℃,回流24小时,利用TLC观察反应,直至反应完全。自然冷却至室温,过滤,将滤液旋蒸至无馏分。所得物质通过硅胶柱(石油醚作为洗脱剂)纯化,得到化合物1。
实施例8:化合物87的合成
(1)将原料8-1(1.7mmol),原料8-2(4.2mmol)、K2CO3(17mmol),DMSO(10ml)加入到三口瓶中,在150℃下加热回流12h。冷却至室温倒入200ml水中析出大量固体搅拌0.5h,抽滤得白色固体,柱层析提纯,收率88.5%,得到中间体8-1。
(2)在氮气气氛下,向三口烧瓶中加入0.01mol中间体8-1、0.025mol原料8-3、0.03mol叔丁醇钠、5×10-5mol Pd2(dba)3和5×10-5mol三叔丁基磷,然后加入150ml甲苯将其溶解,加热至100℃,回流24小时,利用TLC观察反应,直至反应完全。自然冷却至室温,过滤,将滤液旋蒸至无馏分。所得物质通过硅胶柱(石油醚作为洗脱剂)纯化,得到化合物87。表1实施例中化合物的合成方法与实施例1或8类似,所用到的原料1-1或8-1是相同的,区别在于用到的原料1-2或8-2和1-3或8-3有所不同,下表1中列出了原料-2、原料-3及产物的结构式,测试结果也同时在下表1中列出。
表1
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为了对实施例1至15制备的化合物进行结构分析,利用LC-MS测量分子量,且通过在氘代氯仿溶剂中溶解制备的化合物并利用400MHz的NMR设备测量1H-NMR。
表2
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本发明化合物在发光器件中使用,可以作为发光层材料使用。对本发明上述实施例制备的化合物进行物化性质的测试,检测结果如表3所示:
表3
注:玻璃化转变温度Tg由示差扫描量热法(DSC,德国耐驰公司DSC204F1示差扫描量热仪)测定,升温速率10℃/min;最高占据分子轨道HOMO能级是由电离能量测试系统(IPS-3)测试,测试为氮气环境;三线态能级T1是由Horiba的Fluorolog-3系列荧光光谱仪测试,材料的测试条件为2*10-5mol/L的甲苯溶液;S1由Horiba的Fluorolog-3系列荧光光谱仪测试,材料的测试条件为2*10-5mol/L的甲苯溶液,△Est=S1-T1;PLQY、τ由Horiba的Fluorolog-3系列荧光光谱仪测试;光谱变化由纯膜发光峰减去3%掺杂于CBP的共混膜发光峰所得,测试由Horiba的Fluorolog-3系列荧光光谱仪测试。
由上表数据可知,本发明的有机化合物具有合适的能级,可应用于OLED器件的发光层,本发明的有机化合物具有较高的热稳定性,作为发光层材料使用时具有较高效率和较长的寿命。相较于ref-1、ref-2和ref-3,本发明的有机化合物具有较高的PLQY且光谱变化较小,更适合作发光层中的敏化材料。
以下通过器件实施例1-20和器件比较例1-3详细说明本发明合成的OLED材料在器件中的应用效果。
器件实施例1
透明基板层1为透明PI膜,对ITO阳极层2(膜厚为150nm)进行洗涤,即依次进行清洗剂(Semiclean M-L20)洗涤、纯水洗涤、干燥,再进行紫外线-臭氧洗涤以清除透明ITO表面的有机残留物。在进行了上述洗涤之后的ITO阳极层2上,利用真空蒸镀装置,蒸镀膜厚为10nm的HT-1和HI-1作为空穴注入层3,HT-1和HI-1的质量比为97:3。接着蒸镀60nm厚度的HT-1作为空穴传输层4。随后蒸镀30nm厚度的EB-1作为电子阻挡层5。上述电子阻挡材料蒸镀结束后,制作OLED发光器件的发光层6,其结构包括OLED发光层6所使用CBP作为第一主体,使用化合物1作为敏化剂,GD-1作为掺杂材料,CBP、化合物1和GD-1质量比为67:30:3,发光层膜厚为30nm。在上述发光层6之后,继续真空蒸镀HB-1,膜厚为5nm,此层为空穴阻挡层7。在上述空穴阻挡层7之后,继续真空蒸镀ET-1和Liq,ET-1和Liq质量比为1:1,膜厚为30nm,此层为电子传输层8。在电子传输层8上,通过真空蒸镀装置,制作膜厚为1nm的LiF层,此层为电子注入层9。在电子注入层9上,通过真空蒸镀装置,制作膜厚为80nm的Mg:Ag电极层,Mg、Ag质量比为1:9,此层为阴极层10使用。
相关材料的分子结构式如下所示:
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如上所述地完成OLED发光器件后,用公知的驱动电路将阳极和阴极连接起来,测量器件的电流效率、外量子效率和器件的寿命。用同样的方法制备的器件实施例和比较例如表4所示;所得器件的电流效率、外量子效率和寿命的测试结果如表5所示。
表4
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表5
器件实施例 | 电压 | 电流效率(cd/A) | CIEx | CIEy | LT95寿命(H) |
对比例1 | 4.54 | 15.6 | 0.301 | 0.642 | 31.5 |
对比例2 | 4.81 | 16.3 | 0.300 | 0.630 | 21.6 |
对比例3 | 4.69 | 14.7 | 0.298 | 0.648 | 18.7 |
实施例1 | 3.74 | 44.58 | 0.296 | 0.642 | 150.48 |
实施例2 | 3.80 | 43.36 | 0.308 | 0.652 | 156.2 |
实施例3 | 3.92 | 43.91 | 0.299 | 0.634 | 144.76 |
实施例4 | 3.66 | 42.55 | 0.305 | 0.638 | 133.1 |
实施例5 | 3.79 | 39.88 | 0.309 | 0.659 | 127.82 |
实施例6 | 3.81 | 40.53 | 0.306 | 0.621 | 171.6 |
实施例7 | 3.82 | 42.9 | 0.297 | 0.647 | 159.28 |
实施例8 | 3.83 | 41.95 | 0.301 | 0.629 | 144.1 |
实施例9 | 3.68 | 42.6 | 0.299 | 0.642 | 155.54 |
实施例10 | 3.78 | 40.52 | 0.3 | 0.639 | 155.76 |
实施例11 | 3.82 | 44.6 | 0.308 | 0.621 | 151.58 |
实施例12 | 3.74 | 41.67 | 0.308 | 0.639 | 159.06 |
实施例13 | 3.79 | 40.16 | 0.31 | 0.631 | 147.18 |
实施例14 | 3.65 | 40.59 | 0.306 | 0.655 | 162.58 |
实施例15 | 3.69 | 44.57 | 0.302 | 0.66 | 143.44 |
实施例16 | 3.71 | 43.06 | 0.298 | 0.652 | 111.98 |
实施例17 | 3.69 | 42.78 | 0.298 | 0.62 | 115.94 |
实施例18 | 3.73 | 40.15 | 0.309 | 0.644 | 124.52 |
实施例19 | 3.80 | 42.63 | 0.306 | 0.649 | 139.48 |
实施例20 | 3.73 | 40.82 | 0.295 | 0.642 | 143.66 |
注:电压、电流效率、发光峰使用IVL(电流-电压-亮度)测试系统(苏州弗士达科学仪器有限公司),测试条件为10mA/cm2;寿命测试系统为日本系统技研公司EAS-62C型OLED器件寿命测试仪;LT95指的是器件亮度衰减到95%所用时间。
由表5的器件数据结果可以看出,与器件对比例1-3相比,本发明的有机发光器件无论是在器件效率还是器件寿命均相对于已知材料的OLED器件获得较大的提升。
综上,以上仅为本发明的较佳实施例,并不用以限制本发明,凡在本发明的精神和原则之内,所作的任何修改、等同替换、改进等,均应包含在本发明的保护范围之内。
Claims (8)
1.一种以4-氰基吡啶为核心的有机化合物,其特征在于:所述有机化合物结构如通式(1-1)或通式(1-2)所示:
通式(1-1)和通式(1-2)中,Z1每次出现分别独立地表示为C-R3;
R1、R2分别表示为通式(2)或通式(4)所示结构;
通式(2)和通式(4)中,
Z2每次出现分别独立地表示为C-R4;
Z3每次出现分别独立地表示为C或者C-R5;
*标表示与通式(1-1)或通式(1-2)的连接位点;
R3、R4、R5每次出现分别独立的表示为氢、氘、C1~C10烷基、取代或未取代的C6芳基;
X表示为-O-,-S-;
通式(4)与通式(1-1)或通式(1-2)相连处的Z3表示为C;
取代上述可取代基团的取代基任选自氘、苯基中的任意一种。
2.根据权利要求1所述的有机化合物,其特征在于:所述通式(2)表示为以下基团的任一种:
3.根据权利要求1所述的有机化合物,其特征在于:所述通式(4)表示为取代或未取代的以下基团的任一种:
上述基团的取代基任选自氘。
4.根据权利要求1-3任一项所述的有机化合物,其特征在于:所述有机化合物的具体结构式为以下结构中的任一种:
5.一种以4-氰基吡啶为核心的有机化合物,其特征在于:所述有机化合物的具体结构式为以下结构中的任一种:
6.一种有机发光器件,包含阴极、阳极和功能层,所述功能层位于阴极和阳极之间,其特征在于:所述有机发光器件的功能层中包含权利要求1-5任一项所述以4-氰基吡啶为核心的有机化合物。
7.根据权利要求6所述的有机发光器件,所述功能层包含发光层,其特征在于:所述发光层含有权利要求1-5任一项所述以4-氰基吡啶为核心的有机化合物。
8.根据权利要求7所述的有机发光器件,所述发光层包含第一主体材料、第二主体材料和掺杂材料,其特征在于:所述第一主体材料和第二主体材料中至少有一个为TADF材料,且至少有一个为权利要求1-5任一项所述以4-氰基吡啶为核心的有机化合物。
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