CN117069750A - 一种含氮硼的有机化合物、有机电致发光器件和显示装置 - Google Patents
一种含氮硼的有机化合物、有机电致发光器件和显示装置 Download PDFInfo
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- CN117069750A CN117069750A CN202310668844.2A CN202310668844A CN117069750A CN 117069750 A CN117069750 A CN 117069750A CN 202310668844 A CN202310668844 A CN 202310668844A CN 117069750 A CN117069750 A CN 117069750A
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- boron
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- unsubstituted
- nitrogen
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 31
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 title claims abstract description 25
- 229910052796 boron Inorganic materials 0.000 title claims abstract description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title abstract description 18
- 229910052757 nitrogen Inorganic materials 0.000 title abstract description 9
- 239000000463 material Substances 0.000 claims abstract description 21
- TZHYBRCGYCPGBQ-UHFFFAOYSA-N [B].[N] Chemical compound [B].[N] TZHYBRCGYCPGBQ-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000010410 layer Substances 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 19
- -1 benzophenanthryl Chemical group 0.000 claims description 10
- 239000012044 organic layer Substances 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 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 claims description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 3
- 125000001725 pyrenyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
- 125000004306 triazinyl group Chemical group 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000543 intermediate Substances 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 9
- 238000001308 synthesis method Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000004020 luminiscence type Methods 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000010791 quenching Methods 0.000 description 4
- 230000000171 quenching effect Effects 0.000 description 4
- 238000010992 reflux 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
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004537 pulping Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 2
- RFSIFTKIXZLPHR-UHFFFAOYSA-N 3,5-dinitropyridine Chemical compound [O-][N+](=O)C1=CN=CC([N+]([O-])=O)=C1 RFSIFTKIXZLPHR-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 238000004237 preparative chromatography Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- PYUVWRKNVLSJJE-UHFFFAOYSA-N trimethyl(pyridin-4-yl)silane Chemical compound C[Si](C)(C)C1=CC=NC=C1 PYUVWRKNVLSJJE-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- VHHPDZDTKZOHTB-UHFFFAOYSA-M [Br-].[Mg+]C.C1CCOC1 Chemical compound [Br-].[Mg+]C.C1CCOC1 VHHPDZDTKZOHTB-UHFFFAOYSA-M 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 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
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000006757 chemical reactions by type Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- NEXSMEBSBIABKL-UHFFFAOYSA-N hexamethyldisilane Chemical compound C[Si](C)(C)[Si](C)(C)C NEXSMEBSBIABKL-UHFFFAOYSA-N 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
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- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- 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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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1018—Heterocyclic compounds
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Abstract
本发明提供一种含氮硼的有机化合物、有机电致发光器件和显示装置。所述含氮硼的有机化合物具有如下式I所示结构。本发明通过对含氮硼的有机化合物的结构进行设计,得到了性能优异的含氮硼的有机化合物,以本发明提供的含氮硼的有机化合物作为OLED器件发光层材料,制备得到的OLED器件具有较低的驱动电压、较高的电流效率和较长的寿命。
Description
技术领域
本发明属于有机电致发光材料技术领域,具体涉及一种含氮硼的有机化合物、有机电致发光器件和显示装置。
背景技术
有机发光元件(organic light emitting diode;OLED)是利用自发光现象的显示部件,其视角较大,相比于液晶显示部件,OLED元件更轻薄、响应速度更快,且能实现柔性显示,因此作为全彩显示部件或照明用设备的应用备受期待。
通常,有机发光现象是指利用有机物质而将电能转换为光能的现象。利用有机发光现象的有机发光元件通常具有包括阳极、阴极以及夹设于阳极与阴极之间的有机物层的结构。
其中,有机物层为了提高有机发光元件的效率和稳定性而在多数情况下由分别不同的物质构成的多层结构所构成,例如,可由空穴注入层、空穴传输层、发光层、电子传输层、电子注入层等构成。如果在这种有机发光元件的结构中对两个电极之间施加电压,则阳极中的空穴将被注入到有机物层,而阴极中的电子也将被注入到有机物层,当注入的空穴和电子相遇时形成激子(exciton),当该激子释放能量跃迁至基态时将会发射光子,从而产生光。这种有机发光元件被广泛地认识为具有自发光、高亮度、高效率、低驱动电压、宽阔的视野角、高对比度、高速响应性等特性。
目前,有机电致发光材料的研究已经在学术界和工业界广泛开展,其中,蓝光材料是有机电致发光器件的重要组成部分,蓝光材料的传输性能及发光效率制约着发光器件的产业化。因此,设计与寻找一种化合物,作为OLED新型材料以克服其在实际应用过程中出现的不足,是OLED材料研究工作中的重点与今后的研发趋势。
发明内容
针对现有技术的不足,本发明的目的在于提供一种含氮硼的有机化合物、有机电致发光器件和显示装置。本发明通过对含氮硼的有机化合物的结构进行设计,得到了性能优异的含氮硼的有机化合物,以本发明提供的含氮硼的有机化合物作为OLED器件发光层材料,制备得到的OLED器件具有较低的驱动电压、较高的电流效率和较长的寿命。
为达此目的,本发明采用以下技术方案:
第一方面,本发明提供一种含氮硼的有机化合物,所述含氮硼的有机化合物具有如下式I所示结构:
其中,Y选自CR1R2或不存在;
Ar1、Ar2各自独立地选自取代或未取代的芳基、取代或未取代的杂芳基中的任意一种;
R1和R2各自独立地选自取代或未取代的芳基、取代或未取代的杂芳基、烷烃基或氢原子中的任意一种;
Ar1、Ar2、R1和R2中所述取代的取代基选自C1-C5的烷基或C6-C12的芳基中的至少一种。
本发明中,所述含氮硼的有机化合物具有如下式I-1~I-2所示结构:
其中,Ar1、Ar2、R1和R2具有与上述相同的保护范围。
本发明通过结构设计得到的含硼氮的化合物,具有良好的热稳定性及优异的发光性能,可用于制备有机电致发光器件,尤其是作为有机电致发光器件中发光层材料,能够有效降低有机电致发光器件的驱动电压,提高有机电致发光器件的电流效率。
本发明中,所述芳基是指芳烃分子的芳核碳上去掉一个氢原子后,剩下一价基团的总称,其可以为单环芳基或稠环芳基,示例性地包括但不限于:苯基、联苯基、三联苯基、萘基、蒽基、茚基、芴基、苝基、菲基、芘基、荧蒽基、苯并菲基等。
所述杂芳基是指芳基中的一个或多个芳核碳被杂原子替代得到的基团,或者两个相邻的芳环通过杂原子桥接得到的基团的总称,所述杂原子包括但不限于氧、硫和氮原子,所述杂芳基可以为单环杂芳基或稠环杂芳基,示例性地包括但不限于:选自吡啶基、二嗪基、三嗪基、菲啰啉基、喹喔啉基、三氮唑基、二苯并呋喃基(两个相邻的苯环通过O原子桥接)、二苯并噻吩基(两个相邻的苯环通过S原子桥接)等。
本发明中,C1-C5可以是C1、C2、C3、C4或C5。
C6-C12可以是C6、C7、C8、C10或C12等。
以下作为本发明的优选技术方案,但不作为对本发明提供的技术方案的限制,通过以下优选的技术方案,可以更好的达到和实现本发明的目的和有益效果。
作为本发明的优选技术方案,所述Ar1、Ar2各自独立地选自取代或未取代的C6-C50(例如可以是C6、C8、C10、C12、C15、C18、C20、C24、C30、C36、C40、C46或C50等,下同)的芳基、取代或未取代的C4-C50(例如可以是C2、C3、C4、C5、C7、C10、C15、C20、C25、C30、C35、C40、C45或C50等,下同)的杂芳基中的任意一种。
优选地,所述R1和R2各自独立地选自取代或未取代的C6-C50(例如可以是C6、C8、C10、C12、C15、C18、C20、C24、C30、C36、C40、C46或C50等)的芳基、取代或未取代的C3-C50(例如可以是C2、C3、C4、C5、C7、C10、C15、C20、C25、C30、C35、C40、C45或C50等)的芳杂基、C1-C20(例如可以是C1、C2、C4、C6、C8、C10、C12、C14、C16、C18或C20等)的烷烃基或氢原子中的任意一种。
优选地,所述Ar1、Ar2、R1和R2中所述取代的取代基选自甲基、乙基、丙基、丁基、苯基中的至少一种。
作为本发明的优选技术方案,所述取代或未取代的C6-C50的芳基选自苯基、联苯基、三联苯基、萘基、蒽基、茚基、芴基、苝基、菲基、芘基、荧蒽基或苯并菲基中的任意一种。
作为本发明的优选技术方案,所述取代或未取代的C3-C50的芳杂基选自吡啶基、嘧啶基、吡嗪基、三嗪基、菲啰啉基、喹喔啉基、二苯并呋喃基、二苯并噻吩基或三氮唑基中的任意一种。
作为本发明的优选技术方案,所述C1-C20的烷烃基选自甲基、乙基、丙基、异丙基、正丁基、叔丁基、正戊基、异戊基、新戊基、正己基、环己基中的任意一种。
作为本发明的优选技术方案,所述化合物包括化合物1-136中的任意一种:
优选地,所述含氮硼的有机化合物选自如下化合物中的任意一种:
所述含氮硼的有机化合物的制备方法包括但不限于如下方法:(1)合成中间体
中间体A的合成方法包括如下步骤:
中间体B的合成方法包括如下步骤:
(2)合成含氮硼的有机化合物
式I-1含氮硼的有机化合物的合成方法包括如下步骤:
式I-2含氮硼的有机化合物的合成方法包括如下步骤:
其中,Ar1、Ar2、R1、R2具有与上述相同的保护范围。
需要说明的是,本发明对上述反应的条件没有特殊要求,以本领域技术人员熟知的此类反应的常规条件即可。本发明对上述反应中所采用的原料的来源没有特别的限制,原料或中间体可以为市场直售产品或采用本领域技术人员所熟知的制备方法制备得到。
对于本发明所提供的含有硼氮的化合物,其合成方法可以为其他本领域技术人员所熟知的反应类型,上述反应通式仅为其中可行的一种方案。
第二方面,本发明提供一种有机电致发光器件,所述有机电致发光器件包括如第一方面所述的含氮硼的有机化合物。
作为本发明的优选技术方案,所述有机电致发光器件包括第一电极、第二电极和设置于所述第一电极与第二电极之间的有机物层;
所述有机物层的材料包括如第一方面所述含氮硼的有机化合物。
作为本发明的优选技术方案,所述有机层包括发光层;
所述发光层的材料包括如第一方面所述含氮硼的有机化合物。
第三方面,本发明提供一种显示装置,所述显示装置包括如第二方面所述的有机电致发光器件。
与现有技术相比,本发明具有以下有益效果:
本发明通过对含氮硼的有机化合物的结构进行设计,得到了具有特定结构、优异的发光性能的含氮硼的有机化合物,以本发明提供的含氮硼的有机化合物作为OLED器件发光层材料,制备得到的OLED器件具有较低的驱动电压、较高的电流效率和较长的寿命。
具体实施方式
为便于理解本发明,本发明列举实施例如下。本领域技术人员应该明了,所述实施例仅仅是帮助理解本发明,不应视为对本发明的具体限制。
制备例1
本制备例提供一种中间体B及其合成方法,所述合成方法如下:
(1)氮气保护下,将13g甲醇钠及32g六甲基二硅烷加入到160mL六甲基磷酰三胺中,氮气置换5次,确保体系无水无氧,25℃下滴加43g 3-甲酸甲酯-4-溴吡啶到反应瓶中,滴加完毕后,常温反应2h,并加水淬灭反应,用二氯甲烷提取后,浓缩干,得到21g中间体B0;
(2)在200mL高压釜中依次加入上述所得21g中间体B0、15g 4-(三甲基硅基)吡啶、100mL甲苯溶液以及25g(0.1mol)三溴化硼,在120℃搅拌反应12h,反应结束后加入100mL水淬灭,分液,水相用DCM(二氯甲烷,100mL×3)萃取反应液,收集有机相,干燥过滤,旋蒸去除溶剂,用制备色谱分离得到3g中间体B1;
(3)向反应瓶中加入3.6g(0.15mol)镁屑,用约5mL四氢呋喃覆盖住表面,滴加3g3,5-二硝基吡啶,缓慢升温至55℃引发反应,再保持温度滴加剩余的34.2g 3,5-二硝基吡啶的四氢呋喃溶液(加提前加入的3g,共0.15mol,用200mL四氢呋喃稀释),滴加完毕后,保温55℃反应1h,取30g(0.1mol)中间体B1用200mL四氢呋喃溶解并置于1L反应瓶中,降温至10℃左右,缓慢滴加上述制备好格式试剂,滴加过程保持温度处于10~20℃之间,滴加完毕后,升温至常温反应2h,然后缓慢加入到冰水混合物中淬灭反应,分液,水相用的二氯甲烷提取(100mL×3),合并有机相,干燥,过50g中性氧化铝,用制备色谱分离获得1.6g(0.04mol)中间体B,纯度92%。
对化合物B的质谱数据进行测试,测得质谱m/z:393.09。
理论元素含量(%)C17H12BN5O6:C,51.94;H,3.08;B,2.75;N,17.81;O,24.42;实测元素含量(%):C,51.96;H,3.11;N,17.82。
制备例2
将制备例1步骤(1)中的3-甲酸甲酯-4-溴吡啶替换为等物质的量的表1中的原料1,将制备例1步骤(2)中的4-(三甲基硅基)吡啶替换为等物质的量的表1中的原料2,参照制备例1提供的合成方法,分别合成中间体A,其具体结构如下表1所示。
表1
实施例1
本实施例提供一种化合物1及其合成方法,所述合成方法如下:
(1)向50mL单口瓶中加入1.1g中间体A、10g亚磷酸三乙酯升温至152~153℃反应9h,取样过控,原料剩余量<2%,停止反应减压蒸馏除掉亚磷酸三乙酯,然后用5倍甲苯回流打浆,得到0.3g中间体1-A1,纯度为98.5%,;
(2)向体系加入二甲苯60mL、叔丁醇钠5.77g(0.06mol),加入6g(0.023mol)中间体1-A1、溴苯8g(0.051mol)、0.002g Pd2(dba)3、0.014g质量百分含量为10%的三叔丁基膦的甲苯溶液,回流反应4h,取样送检,原料剩余量<0.5%,
停止反应,降至室温,加入50mL水和50mL乙醇,升温至60℃搅拌0.5h,
产品析出,过滤,所得固体用甲苯溶解后过硅胶,所得滤液浓缩至有固体析出,降温至室温抽滤,得到5.9g化合物1,纯度99.8%。
对化合物1的质谱数据进行测试,测得质谱m/z:423.17。
理论元素含量(%)C27H18BN5:C,76.61;H,4.29;B,2.55;N,16.55;实测元素含量(%):C,76.69;H,4.29;N,16.53。
实施例2
本实施例提供一种化合物75及其合成方法,所述合成方法如下:
(1)取20g(0.051mol)中间体B溶解于200mL四氢呋喃中,降温至0~5℃,滴加含有0.2mol的甲基溴化镁四氢呋喃溶液(浓度为1.4M),滴加完毕后,升温至室温搅拌2h,取样送检,原料剩余量<0.5%,将反应液缓慢倒入冰水混合物中淬灭反应,并用甲苯提纯(200mL×2),有机相干燥浓缩至有大量固体析出(约剩余50mL),加入50mL乙醇,降温至室温抽滤,得到5.9g(0.03mol)中间体75-A1,纯度99.2%;
(2)将11.8g中间体75-A1加入到200mL甲苯中,并加入1.3g对甲苯磺酸,升温回流反应,并分水,反应6h取样监控,原料剩余量<1%,加入100mL水,搅拌10min后,分液,有机相干燥后过50g硅胶柱,并用30mL乙醇打浆,抽滤,得到7.5g中间体75-A2,纯度为98.4%;
(3)向250mL单口瓶中加入7.5g中间体75-A2、70g亚磷酸三乙酯升温至152~153℃反应9h,取样过控,原料剩余量<2%,停止反应减压蒸馏除掉亚磷酸三乙酯,然后用5倍甲苯回流打浆,得到3.7g中间体75-A3,纯度为97.9%;
(4)向体系加入二甲苯60mL、叔丁醇钠5.77g(0.06mol),加入7.5g(0.024mol)中间体75-A3、溴苯8g(0.051mol)、0.002g Pd2(dba)3、0.014g三叔丁基膦溶液,回流反应4h,取样送检,原料剩余量<0.5%,停止反应,降至室温,加入50mL水和50mL乙醇,升温至60℃搅拌0.5h,产品析出,过滤,所得固体用甲苯溶解后过硅胶,所得滤液浓缩至有固体析出,降温至室温抽滤,得到5.8g化合物75,纯度99.5%。
对化合物75的质谱数据进行测试,测得质谱m/z:463.20。
理论元素含量(%)C30H22BN5:C,77.77;H,4.79;B,2.33;N,15.11;实测元素含量(%):C,77.79;H,4.81;N,15.09。
其它未列明具体合成步骤的化合物,可以通过本领域公知常识,结合以上实施例提供的合成方法制备得到。
下述器件实施例以及器件对比例中所采用的化合物的具体结构如下所示:
下述器件实施例中选用本发明提供的含硼氮的化合物作为有机电致发光器件中的发光层掺杂材料,器件对比例选用上述BD-1、BD-2、BD-3、BD-4、BD-5以及BD-6作为有机电致发光器件中的发光层掺杂材料。
器件实施例1
器件实施例提供一种有机电致发光器件,以本发明合成实施例1提供的化合物1作为发光层掺杂材料;并且本实施例中,发光层层采用溶液法制备。
所述有机电致发光器件结构为:
ITO/HT(40nm)/BH-1:化合物1 3%/TPBI(30nm)/LiF(0.5nm)/Al(150nm)。
上述有机电致发光器件的制备方法如下:
将涂布了ITO透明导电层(作为阳极)的玻璃基板在清洗剂中进行超声处理,然后在去离子水中冲洗,再在丙酮与乙醇混合溶剂中超声除油,再在洁净环境下烘烤至完全除水,用紫外光和臭氧清洗,并用低能阳离子束轰击表面,以改善表面的性质,提高与空穴注入层的结合能力;
将上述玻璃基板置于真空腔内,抽真空至1×10-5~9×10-3Pa,在阳极上真空蒸镀HT作为空穴传输层,蒸镀速率0.1nm/s,蒸镀膜厚为40nm;
将以上已经蒸镀完毕空穴传输层的玻璃基板转移至充满氮气的手套箱中,在空穴传输层上分别旋涂BH-1及其质量3%的本专利所述化合物或BH-1及其质量3%的对比化合物的4-环己基苯:氯苯=3:1(体积比)溶液,旋涂转速为1000转/min,时间为60秒,然后将上述玻璃基板放在80℃加热2小时,真空除去溶剂,通过调节BH-1和本发明化合物在溶剂中的浓度以及BH-1和对比化合物在溶剂中的浓度,使得到的发光层的厚度在30~40nm左右,列于表2中(发光层膜厚单位为nm)。
将上步已经旋涂上发光层的玻璃基板转移至真空腔室内,在发光层之上真空蒸镀TPBI作为器件的电子传输层,蒸镀速率为0.1nm/s,蒸镀总膜厚为30nm;
在电子传输层上真空蒸镀0.5nm的LiF、150nm的Al作为电子注入层和阴极。
测量了所制备有机电致发光器件的亮度、驱动电压、电流效率。
器件实施例2-8
器件实施例2-8分别提供一种有机电致发光器件,与器件实施例1的区别仅在于,发光层掺杂材料不同(详见下表2),其他条件与器件实施例1相同。
器件对比例1-6
器件对比例1-6分别提供一种有机电致发光器件,与器件实施例1的区别仅在于,发光层掺杂材料不同(详见下表2),其他条件与器件实施例1相同。
性能测试
测试方法:使用杭州远方生产的OLED-1000多通道加速老化寿命与光色性能分析系统测试以上提供的OLED器件的驱动电压、电流效率和寿命LT90;其中,LT90是指保持初始亮度1000nit时的电流密度不变,亮度降至原始亮度90%所需要的时间,测试项目包括有机电致发光器件的亮度、驱动电压、电流效率,驱动电压和电流效率、LT90数据均为亮度为1000cd/m2时的相对值。有机电致发光器件性能测试结果见如下表2:
表2
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由表2的内容可知,本发明通过对含氮硼的有机化合物的结构进行设计,得到了具有特定结构、优异的发光性能的含氮硼的有机化合物,以本发明提供的含氮硼的有机化合物作为OLED器件发光层材料,制备得到的OLED器件具有较低的驱动电压、较高的电流效率和较长的寿命,其驱动电压≤0.969,具体为0.66~0.96,电流效率≥1.12,具体为1.12~1.88,使用使用寿命≥1.09,具体为1.09~1.71。
申请人声明,本发明通过上述实施例来说明本发明的详细工艺流程,但本发明并不局限于上述详细工艺流程,即不意味着本发明必须依赖上述详细工艺流程才能实施。所属技术领域的技术人员应该明了,对本发明的任何改进,对本发明产品各原料的等效替换及辅助成分的添加、具体方式的选择等,均落在本发明的保护范围和公开范围之内。
Claims (10)
1.一种含氮硼的有机化合物,其特征在于,所述含氮硼的有机化合物具有如下式I所示结构:
其中,Y选自CR1R2或不存在;
Ar1、Ar2各自独立地选自取代或未取代的芳基、取代或未取代的杂芳基中的任意一种;
R1和R2各自独立地选自取代或未取代的芳基、取代或未取代的杂芳基、烷烃基或氢原子中的任意一种;
Ar1、Ar2、R1和R2中所述取代的取代基选自C1-C5的烷基或C6-C10的芳基中的至少一种。
2.根据权利要求1所述的含氮硼的有机化合物,其特征在于,所述Ar1、Ar2各自独立地选自取代或未取代的C6-C50的芳基、取代或未取代的C2-C50的杂芳基中的任意一种;
优选地,所述R1和R2各自独立地选自取代或未取代的C6-C50的芳基、取代或未取代的C2-C50的芳杂基、C1-C20的烷烃基或氢原子中的任意一种;
优选地,所述Ar1、Ar2、R1和R2中所述取代的取代基选自甲基、乙基、丙基、丁基、苯基中的至少一种。
3.根据权利要求2所述的含氮硼的有机化合物,其特征在于,所述取代或未取代的C6-C50的芳基选自苯基、联苯基、三联苯基、萘基、蒽基、茚基、芴基、苝基、菲基、芘基、荧蒽基或苯并菲基中的任意一种。
4.根据权利要求2所述的含硼氮的化合物,其特征在于,所述取代或未取代的C3-C50的芳杂基选自吡啶基、嘧啶基、吡嗪基、三嗪基、菲啰啉基、喹喔啉基、二苯并呋喃基、二苯并噻吩基或三氮唑基中的任意一种。
5.根据权利要求2所述的含硼氮的化合物,其特征在于,所述C1-C20的烷烃基选自甲基、乙基、丙基、异丙基、正丁基、叔丁基、正戊基、异戊基、新戊基、正己基、环己基中的任意一种。
6.根据权利要求1-5任一项所述的含硼的化合物,其特征在于,所述化合物包括化合物1-136中的任意一种:
7.一种有机电致发光器件,其特征在于,所述有机电致发光器件包括如权利要求1-6任一项所述的含硼氮的化合物。
8.根据权利要求8所述的有机电致发光器件,其特征在于,所述有机电致发光器件包括第一电极、第二电极和设置于所述第一电极与第二电极之间的有机物层;所述有机物层的材料包括如权利要求1-6任一项所述含硼氮的化合物。
9.根据权利要求9所述的有机电致发光器件,其特征在于,所述有机层包括发光层;所述发光层的材料包括如权利要求1-6任一项所述含硼氮的化合物。
10.一种显示装置,其特征在于,所述显示装置包括如权利要求7-10任一项所述的有机电致发光器件。
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