CN111333483B - 一种芘类蓝色有机荧光材料及其制备方法和应用 - Google Patents
一种芘类蓝色有机荧光材料及其制备方法和应用 Download PDFInfo
- Publication number
- CN111333483B CN111333483B CN202010174843.9A CN202010174843A CN111333483B CN 111333483 B CN111333483 B CN 111333483B CN 202010174843 A CN202010174843 A CN 202010174843A CN 111333483 B CN111333483 B CN 111333483B
- Authority
- CN
- China
- Prior art keywords
- pyrene
- fluorescent material
- organic fluorescent
- blue organic
- molecules
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 239000000463 material Substances 0.000 title claims abstract description 71
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 title claims abstract description 71
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title claims abstract description 22
- 125000005581 pyrene group Chemical group 0.000 claims abstract description 7
- -1 azacycles Chemical class 0.000 claims abstract description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 66
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- HSOBXXGBOLCELM-UHFFFAOYSA-N 5,9-dibromo-7-tert-butyl-1,3-diphenylpyrene Chemical compound C(C)(C)(C)C=1C=C2C(=CC3=C(C=C(C4=CC(=C(C=1)C2=C43)Br)C1=CC=CC=C1)C1=CC=CC=C1)Br HSOBXXGBOLCELM-UHFFFAOYSA-N 0.000 claims description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 6
- 150000007529 inorganic bases Chemical class 0.000 claims description 6
- 150000007530 organic bases Chemical class 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 claims description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical group [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 4
- IBXMKLPFLZYRQZ-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical group [Pd].[Pd].C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 IBXMKLPFLZYRQZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 claims description 2
- 229910052808 lithium carbonate Inorganic materials 0.000 claims description 2
- 239000012046 mixed solvent Substances 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 239000004327 boric acid Substances 0.000 claims 1
- 238000002347 injection Methods 0.000 abstract description 12
- 239000007924 injection Substances 0.000 abstract description 12
- 125000000641 acridinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 abstract description 4
- 125000001484 phenothiazinyl group Chemical class C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 abstract description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract description 4
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract description 3
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 abstract description 3
- 238000009825 accumulation Methods 0.000 abstract description 2
- 150000001454 anthracenes Chemical class 0.000 abstract description 2
- 235000010290 biphenyl Nutrition 0.000 abstract description 2
- 150000004074 biphenyls Chemical class 0.000 abstract description 2
- 230000021615 conjugation Effects 0.000 abstract description 2
- 150000002790 naphthalenes Chemical class 0.000 abstract description 2
- 230000007935 neutral effect Effects 0.000 abstract description 2
- 150000004893 oxazines Chemical class 0.000 abstract description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract 1
- 150000002991 phenoxazines Chemical class 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
- 150000001875 compounds Chemical class 0.000 description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
- 238000001228 spectrum Methods 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 11
- 238000004440 column chromatography Methods 0.000 description 9
- 238000005401 electroluminescence Methods 0.000 description 9
- 239000003480 eluent Substances 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 238000002390 rotary evaporation Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 7
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 238000010586 diagram Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 238000000295 emission spectrum Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000011259 mixed solution Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 3
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical group N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- IRDQNLLVRXMERV-UHFFFAOYSA-N CCCC[Na] Chemical group CCCC[Na] IRDQNLLVRXMERV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000005577 anthracene group Chemical group 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000005525 hole transport Effects 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 230000005693 optoelectronics Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- DQVXWCCLFKMJTQ-UHFFFAOYSA-N (4-methylphenoxy)boronic acid Chemical compound CC1=CC=C(OB(O)O)C=C1 DQVXWCCLFKMJTQ-UHFFFAOYSA-N 0.000 description 1
- XPEIJWZLPWNNOK-UHFFFAOYSA-N (4-phenylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC=C1 XPEIJWZLPWNNOK-UHFFFAOYSA-N 0.000 description 1
- MNJYZNVROSZZQC-UHFFFAOYSA-N (4-tert-butylphenyl)boronic acid Chemical compound CC(C)(C)C1=CC=C(B(O)O)C=C1 MNJYZNVROSZZQC-UHFFFAOYSA-N 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 150000001543 aryl boronic acids Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 239000002800 charge carrier Substances 0.000 description 1
- 238000004140 cleaning Methods 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
- 238000010304 firing Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/38—Polycyclic condensed hydrocarbons containing four rings
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
本发明公开了一种芘类蓝色有机荧光材料及其制备方法和应用。该材料的结构式为:其中Ar是单苯类、联苯类、萘类、蒽类、吩噻嗪类、吩噁嗪类、吖啶类、咔唑类、苯氨基类、磺酰基类、氮杂环类、嗪类等基团。通过在芘的活性1,3位引入中性富π电子的苯基来拓展分子的π共轭度,提高材料分子的发光量子效率,在芘的K‑区5,9位引入不同具有吸电子特性或供电子特性的大的基团来改变分子的共轭形态、分子内电荷转移路径(ICT)和抑制分子间的π‑π堆积,实现材料分子的蓝光发射及OLED应用中载流子注入的平衡,同时实现材料分子发光颜色的调制。本发明的蓝色有机荧光材料分子具有很好的光化学、热稳定性和高的发光量子效率,可作为OLED器件发光层的主体或客体材料。
Description
技术领域
本发明属于有机电致发光器件技术领域,具体涉及一种芘类蓝色有机荧光材料及其制备方法和应用。
背景技术
有机电致发光现象是Pope等人在1963年首次发现的。1987年,美国柯达公司通过蒸镀有机小分子的方法首次制备了非晶膜有机电致发光器件(OLED),从而将器件驱动电压降低到20V以内。OLED器件具有超轻薄,自发光,高亮度,宽视角,快响应,驱动电压低,功耗小等优点,可广泛应用于平板显示器和面光源领域之中,因此得到了广泛关注与研究。
经过三十多年的发展,OLED材料已经实现了蓝、绿、红色发光。在全彩色显示领域中,要求蓝色、绿色和红色发光体具有高发射效率和高色纯度。其中绿色和红色发光体通常用于磷光系统,而蓝色发光体仍然用于荧光系统。目前蓝色发光体的颜色稳定性和寿命仍然面临着挑战。
发明内容
本发明的目的是提供一种热稳定性好、发光量子效率高的芘类蓝色有机荧光材料,并为该材料提供一种制备方法和新的应用。
针对上述目的,本发明芘类蓝色有机荧光材料的结构式如下所示:
其中:Ar代表单苯类基团、联苯类基团、萘类基团、蒽类基团、吩噻嗪类基团、吩噁嗪类基团、吖啶类基团、咔唑类基团、苯氨基类基团、磺酰基类基团、氮杂环类基团、嗪类基团中任意一种。
上述的单苯类基团选自下述任意一种:
上述的联苯类基团选自下述任意一种:
上述的萘类基团选自下述任意一种:
上述的蒽类基团选自下述任意一种:
上述的吩噻嗪类基团选自下述任意一种:
上述的吩噁嗪类基团选自下述任意一种:
上述的吖啶类基团选自下述任意一种:
上述的咔唑类基团选自下述任意一种:
上述的苯氨基类基团选自下述任意一种:
上述的磺酰基类基团选自下述任意一种:
上述的氮杂环类基团选自下述任意一种:
上述的嗪类基团选自下述任意一种:
本发明芘类蓝色有机荧光材料的结构式中,优选Ar选自 中任意一种。
本发明芘类蓝色有机荧光材料的结构式中Ar单元通过C原子与芘单元相连时,其制备方法为:将7-叔丁基-1,3-二苯-5,9-二溴芘与式I所示芳基硼酸、四(三苯基膦)钯、无机碱加入甲苯与乙醇体积比为4:1的混合溶剂中,在100~120℃下反应16~24小时,得到芘类蓝色有机荧光材料,具体反应方程式如下:
上述的7-叔丁基-1,3-二苯-5,9-二溴芘与芳基硼酸、四(三苯基膦)钯、无机碱的摩尔比为1:1.5~3:0.08~0.20:30~50,其中所述的无机碱为碳酸钾、碳酸钠、碳酸铯、碳酸锂中任意一种。
本发明芘类蓝色有机荧光材料的结构式中Ar单元通过N原子与芘单元相连时,其制备方法为:将7-叔丁基-1,3-二苯-5,9-二溴芘与式II所示芳烃、钯催化剂、有机碱、三叔丁基膦加入甲苯中,在60~80℃下反应8~16小时,得到芘类蓝色有机荧光材料,具体反应方程式如下:
上述的7-叔丁基-1,3-二苯-5,9-二溴芘与芳烃、钯催化剂、有机碱、三叔丁基膦的摩尔比为1:2~3:0.06~0.10:8~12:0.1~0.2,其中所述的钯催化剂为三二亚苄基丙酮二钯或四(三苯基膦)钯,所述的有机碱为叔丁醇钠或双(三甲硅基)氨基钠。
本发明芘类蓝色有机荧光材料具有良好的热稳定性好和较高的发光量子效率,可作为有机电致发光器件发光层主体材料和发光层客体材料应用。
本发明的有益效果如下:
1、本发明的荧光材料能够实现蓝光发射。在芘的活性1,3位其中Ar是单苯类、联苯类、萘类、蒽类、吩噻嗪类、吩噁嗪类、吖啶类、咔唑类、苯氨基类、磺酰基类、氮杂环类、嗪类等基团。在芘的活性1,3位引入中性富π电子的苯基来拓展分子的π共轭度,提高材料分子的发光量子效率,在芘的K-区5,9位引入不同具有吸电子特性或供电子特性的大的基团来改变分子的共轭形态、分子内电荷转移路径(ICT)和抑制分子间的π-π堆积,实现材料分子的蓝光发射及OLED应用中载流子注入的平衡,同时实现材料分子发光颜色的调制。此外,芘的1,3,5,9位大的空间位阻基团和7位叔丁基的存在,能有效地抑制分子间的π-π堆叠相互作用,能进一步提高了材料分子的发光量子效率。
2、本发明荧光材料的制备方法具有步骤简单、成本低、产率高、易提纯等特点。所制备的荧光材料在紫外光照射下,溶液或薄膜都呈现强的蓝色荧光发射,具有荧光量子产率高、荧光寿命长、电荷载流子迁移率高和光化学、热稳定性好等优点,在有机显示、有机固态照明等领域具有一定的应用价值和市场前景。
3、本发明有机荧光材料应用在OLED器件中,作为主体材料制备的器件性能优、外量子效率(EQE)高,实现了低电压驱动的掺杂蓝色高效OLED器件的制备;作为客体材料制备的器件性能优,色纯度好,实现了低电压驱动、色纯度好掺杂蓝色OLED器件的制备。
附图说明
图1是实施例1制得的芘类蓝色有机荧光材料a的核磁共振氢谱图。
图2是实施例1制得的芘类蓝色有机荧光材料a的核磁共振碳谱图。
图3是实施例1制得的芘类蓝色有机荧光材料a的热重图。
图4是器件A1的电致发光(EL)图。
图5是器件A1的电流密度-外部量子效率(Cd-EQE)的图谱曲线。
图6是器件A1的电流密度-电压-亮度(Cd-V-L)图谱曲线。
图7是器件A2的电致发光(EL)图。
图8是器件A2的电流密度-外部量子效率(Cd-EQE)的图谱曲线。
图9是器件A2的电流密度-电压-亮度(Cd-V-L)图谱曲线。
图10是器件B1的电致发光(EL)图。
图11是器件B1的电流密度-外部量子效率(Cd-EQE)的图谱曲线。
图12是器件B1的电流密度-电压-亮度(Cd-V-L)图谱曲线。
图13是器件B2的电致发光(EL)图。
图14是器件B2的电流密度-外部量子效率(Cd-EQE)的图谱曲线。
图15是器件B2的电流密度-电压-亮度(Cd-V-L)图谱曲线。
具体实施方式
下面结合附图和实施例对本发明进一步详细说明,但本发明的保护范围不仅限于这些实施例。
实施例1
制备结构式如下的化合物a
在氮气保护下,在反应瓶中加入0.568g(1mmol)7-叔丁基-1,3-二苯基-5,9-二溴芘、0.408g(3mmol)4-甲苯基硼酸、0.116g(0.1mmol)四(三苯基膦)钯、5.52g(40mmol)K2CO3、40mL甲苯、10mL乙醇,混合均匀,在110℃下搅拌反应24小时,反应结束后,用甲苯萃取,有机相经旋转蒸发浓缩后,柱层析(洗脱剂是正己烷与二氯甲烷体积比2:1的混合液)纯化,再用正己烷重结晶,得到化合物a,产率为73%。
所得化合物a的核磁共振氢谱数据为:1H NMR(300MHz,CDCl3):δ=1.38(s,9H),2.48(s,6H),7.33(m,4H),7.42(d,J=7.2Hz,2H),7.52(m,8H),7.68(d,J=6.9Hz,4H),7.96(s,1H),8.14(s,2H),8.32(s,2H)ppm,核磁共振氢谱如图1所示;核磁共振碳谱数据为:13CNMR(100MHz,CDCl3):δ=148.60,141.26,139.80,138.52,137.12,130.68,130.10,129.16,128.50,127.43,127.24,125.58,124.42,124.23,121.47,35.53,31.80,21.39ppm,核磁共振碳谱如图2所示;其分子式为C46H38,分子量为590。由图3可见,该化合物热分解温度为345℃,具有良好的热稳定性,满足使用真空蒸镀法来制备器件的要求。
实施例2
制备结构式如下的化合物b
在氮气保护下,在反应瓶中加入0.568g(1mmol)7-叔丁基-1,3-二苯基-5,9-二溴芘、0.593g(3mmol)4-叔丁基苯硼酸、0.116g(0.1mmol)四(三苯基膦)钯、5.52g(40mmol)K2CO3、40mL甲苯、10mL乙醇,混合均匀,在110℃下搅拌反应24小时,反应结束后,用甲苯萃取,有机相经旋转蒸发浓缩后,柱层析(洗脱剂是正己烷与二氯甲烷体积比1:1的混合液)纯化,再用正己烷重结晶,得到化合物b,产率为68%。
所得化合物b的核磁共振氢谱数据为:1H NMR(300MHz,CDCl3):δ=CDCl31.43(s,18H),1.39(s,9H),7.56(m,14H),7.70(d,J=6.9Hz,4H),7.95(s,1H,),8.16(s,2H),8.37(s,2H)ppm.13C NMR(100MHz,CDCl3):δ=150.24,148.48,141.22,139.63,138.34,136.97,130.63,129.80,128.42,128.21,127.36,127.13,125.57,125.36,123.23,121.40,35.45,34.66,33.01,31.54,31.46ppm;其分子式为C52H50,分子量为674。
实施例3
制备结构式如下的化合物c
在氮气保护下,在反应瓶中加入0.568g(1mmol)7-叔丁基-1,3-二苯基-5,9-二溴芘、0.516g(3mmol)1-萘硼酸、0.116g(0.1mmol)四(三苯基膦)钯、5.52g(40mmol)K2CO3、40mL甲苯、10mL乙醇,混合均匀,在110℃下搅拌反应24小时,反应结束后,用甲苯萃取,有机相经旋转蒸发浓缩后,柱层析(洗脱剂是正己烷与二氯甲烷体积比10:1的混合液)纯化,再用正己烷重结晶,得到化合物c,产率为73%,其分子式为C52H38,分子量为662。
实施例4
制备结构式如下的化合物d
在氮气保护下,在反应瓶中加入0.784g(1.38mmol)7-叔丁基-1,3-二苯基-5,9-二溴芘、0.607g(3.59mmol)二苯胺、0.101g(0.11mmol)三二亚苄基丙酮二钯、1.33g(13.8mmol)叔丁醇钠、50mL甲苯,充分搅拌混合均匀,然后加入0.032g(0.16mmol)三叔丁基膦,在70℃下搅拌反应12小时,反应结束后,用甲苯萃取,有机相经旋转蒸发浓缩后,柱层析(洗脱剂是正己烷与二氯甲烷体积比10:1的混合液)纯化,再用正己烷重结晶,得到化合物d,产率为26.6%,其分子式为C56H44N2,分子量为744。实施例5
制备结构式如下的化合物e
在氮气保护下,在反应瓶中加入0.568g(1mmol)7-叔丁基-1,3-二苯基-5,9-二溴芘、0.594g(3mmol)4-苯基苯硼酸、0.116g(0.1mmol)四(三苯基膦)钯、5.52g(40mmol)K2CO3、40mL甲苯、10mL乙醇,混合均匀,在110℃下搅拌反应24小时,反应结束后,用甲苯萃取,有机相经旋转蒸发浓缩后,柱层析(洗脱剂是正己烷与二氯甲烷体积比8:1的混合液)纯化,再用正己烷重结晶,得到化合物e,产率为74%,其分子式为C56H42,分子量为714。
实施例6
制备结构式如下的化合物f
在氮气保护下,在反应瓶中加入0.568g(1mmol)7-叔丁基-1,3-二苯基-5,9-二溴芘、0.963g(3mmol)4-吩噻嗪基笨硼酸、0.116g(0.1mmol)四(三苯基膦)钯、5.52g(40mmol)K2CO3、40mL甲苯、10mL乙醇,混合均匀,在110℃下搅拌反应24小时,反应结束后,用甲苯萃取,有机相经旋转蒸发浓缩后,柱层析(洗脱剂是正己烷与二氯甲烷体积比8:1的混合液)纯化,再用正己烷重结晶,得到化合物f,产率为70%,其分子式为C68H52N2S2,分子量为960。
实施例7
制备结构式如下的化合物g
在氮气保护下,在反应瓶中加入0.568g(1mmol)7-叔丁基-1,3-二苯基-5,9-二溴芘、0.915g(3mmol)4-吩噁嗪基笨硼酸、0.116g(0.1mmol)四(三苯基膦)钯、5.52g(40mmol)K2CO3、40mL甲苯、10mL乙醇,混合均匀,在110℃下搅拌反应24小时,反应结束后,用甲苯萃取,有机相经旋转蒸发浓缩后,柱层析(洗脱剂是正己烷与二氯甲烷体积比8:1的混合液)纯化,再用正己烷重结晶,得到化合物g,产率为71%,其分子式为C68H52N2O2,分子量为928。
实施例8
制备结构式如下的化合物h
/>
在氮气保护下,在反应瓶中加入0.568g(1mmol)7-叔丁基-1,3-二苯基-5,9-二溴芘、0.909g(3mmol)4-吖啶基笨硼酸、0.116g(0.1mmol)四(三苯基膦)钯、5.52g(40mmol)K2CO3、40mL甲苯、10mL乙醇,混合均匀,在110℃下搅拌反应24小时,反应结束后,用甲苯萃取,有机相经旋转蒸发浓缩后,柱层析(洗脱剂是正己烷与二氯甲烷体积比8:1的混合液)纯化,再用正己烷重结晶,得到化合物h,产率为72%,其分子式为C70H56N2,分子量为924。
实施例9
制备结构式如下的化合物i
在氮气保护下,在反应瓶中加入0.784g(1.38mmol)7-叔丁基-1,3-二苯基-5,9-二溴芘、0.600g(3.59mmol)咔唑、0.101g(0.11mmol)三二亚苄基丙酮二钯、1.33g(13.8mmol)叔丁醇钠、50mL甲苯,充分搅拌混合均匀,然后加入0.032g(0.16mmol)三叔丁基膦,在70℃下搅拌反应12小时,反应结束后,用甲苯萃取,有机相经旋转蒸发浓缩后,柱层析(洗脱剂是正己烷与二氯甲烷体积比10:1的混合液)纯化,再用正己烷重结晶,得到化合物i,产率为37.8%,其分子式为C56H40N2,分子量为740。
实施例10
本发明芘类蓝色有机荧光材料作为有机电致发光器件发光层主体材料和客体材料的应用
采用实施例1~4制备的化合物制备有机电致发光器件A1、A2、B1、B2,具体制备方法为:依次用洗洁精、去离子水、四氢呋喃、异丙醇超声清洗ITO玻璃各20分钟,然后在等离子体清洗器中处理10分钟,其方阻为15~20Ω/sq;在清洗后的ITO玻璃上真空蒸镀厚度为5nm的空穴注入层HAT-CN,在空穴注入HAT-CN上真空蒸镀厚度为40nm的空穴传输层TAPC,在空穴传输层TAPC上真空蒸镀厚度为20nm的发光层,在发光层上真空蒸镀厚度为40nm的电子传输层B3PyPB,在电子传输层上真空蒸镀厚度为1nm的电子注入层LiF,在电子注入层上真空蒸镀厚度为100nm的阴极Al。
按照上述方法制备的有机电致发光器件A1的发光层的主体材料为化合物a,客体材料为DSA-ph,DSA-ph与化合物a的质量比为5:95;A1的结构为依次叠层的ITO(110nm)/HAT-CN(5nm)/TAPC(40nm)/EML:[5%DSA-ph:a(20nm)]/B3PyPB(40nm)/LiF(1nm)/Al(100nm)。
按照上述方法制备的有机电致发光器件A2的发光层的主体材料为化合物b,客体材料为DSA-ph,DSA-ph与化合物b的质量比为5:95;A2的结构为依次叠层的ITO(110nm)/HAT-CN(5nm)/TAPC(40nm)/EML:[5%DSA-ph:b(20nm)]/B3PyPB(40nm)/LiF(1nm)/Al(100nm)。
按照上述方法制备的有机电致发光器件B1的发光层的主体材料为CBP,客体材料为化合物a,化合物a与CBP的质量比为5:95;B1的结构为依次叠层的ITO(110nm)/HAT-CN(5nm)/TAPC(40nm)/EML:[5%a:CBP(20nm)]/B3PyPB(40nm)/LiF(1nm)/Al(100nm)。
按照上述方法制备的有机电致发光器件B2的发光层的主体材料为CBP,客体材料为化合物b,化合物b与CBP的质量比为5:95;B2的结构为依次叠层的ITO(110nm)/HAT-CN(5nm)/TAPC(40nm)/EML:[5%b:CBP(20nm)]/B3PyPB(40nm)/LiF(1nm)/Al(100nm)。
上述HAT-CN、TAPC、DSA-ph、B3PyPB、CBP的结构式如下:
上述器件A1的发光图谱、电流密度-外部量子效率的图谱曲线、电流密度-电压-亮度图谱曲线分别如图4、图5、图6所示,器件A2的发光图谱、电流密度-外部量子效率的图谱曲线、电流密度-电压-亮度图谱曲线分别如图7、图8、图9所示,器件B1的发光图谱、电流密度-外部量子效率的图谱曲线、电流密度-电压-亮度图谱曲线、分别如图10、图11、图12所示,器件B2的发光图谱、电流密度-外部量子效率的图谱曲线、电流密度-电压-亮度图谱曲线、分别如图13、图14、图15所示。各器件的光电参数见表1。
表1各电致发光器件的光电参数
注:表中Von代表点亮电压,CEmax代表最大电流效率,PEmax代表最大功率效率,EQEmax代表最大外部量子效率,EQE500代表在500cd/A时的最大外部量子效率,CIE(x,y)代表色纯度坐标(CIE)。
从图4可以得出:器件A1是来自于客体材料DSA-ph的发光,说明器件能量转移完全。从图5可以得出,器件A1的最大EQE达到6.00%且效率滚降很小,说明器件效率稳定性好,并且最大电流效率(CE)为11.39Cd/A,最大功率效率(PE)为12.78lm/w,器件综合性能优异。从图6得出:器件A1点亮电压低于3.0V,说明器件电荷注入良好,化合物a作为主体材料具备优良的电荷注入及传输的能力。
从图7可以得出:器件A2是来自于客体材料DSA-ph的发光,说明器件能量转移完全。从图8可以得出,器件A2的最大EQE达到5.00%且效率滚降很小,说明器件效率稳定性好并且最大电流效率(CE)为10.57Cd/A,最大功率效率(PE)为12.78lm/w,器件综合性能优异。从图9得出:器件A2点亮电压低于3.0V,说明器件电荷注入良好,化合物b作为主体材料具备优良的电荷注入及传输的能力。
从图10可以得出:器件B1是来自于客体材料a的发光,说明器件能量转移完全。从图11可以得出,器件B1的最大EQE达到3.00%且效率滚降较小,说明器件效率稳定性好并且最大电流效率(CE)为1.15Cd/A,最大功率效率(PE)为1.13lm/w,器件综合性能优异。同时器件的色度坐标为(0.15,0.05),说明器件具有良好的色纯度。从图12得出:器件B1点亮电压为3.2V,说明器件电荷注入良好。
从图13可以得出:器件B2是来自于客体材料b的发光,说明器件能量转移完全。从图14可以得出,器件B2的最大EQE达到2.97%且效率滚降较小,说明器件效率稳定性好并且最大电流效率(CE)为1.25Cd/A,最大功率效率(PE)为1.31lm/w,器件综合性能优异。同时器件的色度坐标为(0.15,0.05),说明器件具有良好的色纯度。从图15得出:器件B2点亮电压为3.4V,说明器件电荷注入良好。
由上述试验结果可见,本发明芘类蓝色有机荧光材料具有良好的热稳定性和较高的发光量子效率,作为有机电致发光器件发光层主体材料,具有较高的载流子迁移率,可实现充分的主客体能量传递,作为有机电致发光器件发光层客体材料,可实现色纯度好,性能优异的蓝色发光器件。
Claims (8)
1.一种芘类蓝色有机荧光材料,其特征在于该材料的结构式如下:
所述的Ar选自中任意一种。
2.一种权利要求1所述的芘类蓝色有机荧光材料的制备方法,其特征在于:
所述芘类蓝色有机荧光材料结构式中 Ar 单元通过 C 原子与芘单元相连时,制备方法为:将 7-叔丁基-1,3-二苯-5,9-二溴芘与式 I 所示芳基硼酸、四(三苯基膦)钯、无机碱加入甲苯与乙醇体积比为 4:1 的混合溶剂中,在 100~120℃下反应 16~24 小时,得到芘类蓝色有机荧光材料;
所述芘类蓝色有机荧光材料结构式中 Ar 单元通过 N 原子与芘单元相连时,制备方法为:将 7-叔丁基-1,3-二苯-5,9-二溴芘与式 II 所示芳烃、钯催化剂、有机碱、三叔丁基膦加入甲苯中,在 60~80℃下反应 8~16 小时,得到芘类蓝色有机荧光材料;
上述的钯催化剂为三二亚苄基丙酮二钯或四(三苯基膦)钯。
3.根据权利要求2所述的芘类蓝色有机荧光材料的制备方法,其特征在于:所述的7-叔丁基-1,3-二苯-5,9-二溴芘与芳基硼酸、四(三苯基膦)钯、无机碱的摩尔比为1:1.5~3:0.08~0.20:30~50。
4.根据权利要求2所述的芘类蓝色有机荧光材料的制备方法,其特征在于:所述的无机碱为碳酸钾、碳酸钠、碳酸铯、碳酸锂中任意一种。
5.根据权利要求2所述的芘类蓝色有机荧光材料的制备方法,其特征在于:所述的7-叔丁基-1,3-二苯-5,9-二溴芘与芳烃、钯催化剂、有机碱、三叔丁基膦的摩尔比为 1:2~3:0.06~0.10:8~12:0.1~0.2。
6.根据权利要求 2所述的芘类蓝色有机荧光材料的制备方法,其特征在于:所述的有机碱为叔丁醇钠或双(三甲硅基)氨基钠。
7.权利要求1的芘类蓝色有机荧光材料作为有机电致发光器件发光层主体材料的应用。
8.权利要求1的芘类蓝色有机荧光材料作为有机电致发光器件发光层客体材料的应用。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202010174843.9A CN111333483B (zh) | 2020-03-13 | 2020-03-13 | 一种芘类蓝色有机荧光材料及其制备方法和应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202010174843.9A CN111333483B (zh) | 2020-03-13 | 2020-03-13 | 一种芘类蓝色有机荧光材料及其制备方法和应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN111333483A CN111333483A (zh) | 2020-06-26 |
CN111333483B true CN111333483B (zh) | 2024-01-26 |
Family
ID=71180068
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202010174843.9A Active CN111333483B (zh) | 2020-03-13 | 2020-03-13 | 一种芘类蓝色有机荧光材料及其制备方法和应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN111333483B (zh) |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103539725A (zh) * | 2013-05-17 | 2014-01-29 | Tcl集团股份有限公司 | 四芳基芘类衍生物、制备方法和应用及电致发光器件 |
CN104876825A (zh) * | 2015-04-30 | 2015-09-02 | 北京印刷学院 | 一种芘的衍生物及其制备方法和应用 |
KR20160056522A (ko) * | 2014-11-12 | 2016-05-20 | (주)피엔에이치테크 | 유기발광 화합물 및 이를 포함하는 유기전계발광소자 |
CN109233813A (zh) * | 2018-10-19 | 2019-01-18 | 陕西师范大学 | 一种近紫外色有机电致发光器件及其制备方法 |
CN110002946A (zh) * | 2019-04-25 | 2019-07-12 | 陕西师范大学 | 一种芘基蓝色聚集诱导发光材料及其制备方法和应用 |
CN110183315A (zh) * | 2019-06-10 | 2019-08-30 | 南京邮电大学 | 一种芘衍生物材料及其制备方法与应用 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20140087828A (ko) * | 2012-12-31 | 2014-07-09 | 삼성디스플레이 주식회사 | 축합환 화합물 및 이를 포함하는 유기 전계 발광 소자 |
-
2020
- 2020-03-13 CN CN202010174843.9A patent/CN111333483B/zh active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103539725A (zh) * | 2013-05-17 | 2014-01-29 | Tcl集团股份有限公司 | 四芳基芘类衍生物、制备方法和应用及电致发光器件 |
KR20160056522A (ko) * | 2014-11-12 | 2016-05-20 | (주)피엔에이치테크 | 유기발광 화합물 및 이를 포함하는 유기전계발광소자 |
CN104876825A (zh) * | 2015-04-30 | 2015-09-02 | 北京印刷学院 | 一种芘的衍生物及其制备方法和应用 |
CN109233813A (zh) * | 2018-10-19 | 2019-01-18 | 陕西师范大学 | 一种近紫外色有机电致发光器件及其制备方法 |
CN110002946A (zh) * | 2019-04-25 | 2019-07-12 | 陕西师范大学 | 一种芘基蓝色聚集诱导发光材料及其制备方法和应用 |
CN110183315A (zh) * | 2019-06-10 | 2019-08-30 | 南京邮电大学 | 一种芘衍生物材料及其制备方法与应用 |
Non-Patent Citations (6)
Also Published As
Publication number | Publication date |
---|---|
CN111333483A (zh) | 2020-06-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR101551207B1 (ko) | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고 있는 유기 발광 소자 | |
KR101427605B1 (ko) | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계발광 소자 | |
KR101376530B1 (ko) | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고 있는 유기 발광 소자 | |
KR20100109293A (ko) | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계발광 소자 | |
KR20100109050A (ko) | 신규한 유기 발광 화합물 및 이를 포함하는 유기 전계 발광소자 | |
KR20100118700A (ko) | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자 | |
KR101645949B1 (ko) | 유기발광화합물을 발광재료로서 채용하고 있는 유기 전계 발광 소자 | |
KR20110116635A (ko) | 신규한 유기 전자재료용 화합물 및 이를 채용하고 있는 유기 전계 발광 소자 | |
KR20100108924A (ko) | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계발광 소자 | |
KR20130127014A (ko) | 유기전기발광화합물을 발광재료로서 채용하고 있는 유기전기발광소자 | |
KR20120020901A (ko) | 신규한 유기 전자재료용 화합물 및 이를 채용하고 있는 유기 전계 발광 소자 | |
KR20110113297A (ko) | 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자 | |
CN110330481B (zh) | 一种红色磷光化合物和使用该化合物的有机发光器件 | |
CN109593097B (zh) | 一种磷光主体化合物及其使用该化合物的有机电致发光器件 | |
KR20120038056A (ko) | 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자 | |
KR20120033017A (ko) | 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자 | |
CN109678875B (zh) | 一种磷光化合物和使用该化合物的有机发光二极管器件 | |
CN111675701B (zh) | 一种基于三苯胺结构的有机电致发光化合物及有机电致发光器件 | |
KR20100108909A (ko) | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계발광 소자 | |
CN111153888A (zh) | 一种磷光化合物和使用该化合物的有机发光二极管器件 | |
KR20120020818A (ko) | 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자 | |
KR20130058027A (ko) | 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전자 소자 | |
KR20100118258A (ko) | 신규한 유기 발광 화합물 및 이를 채용하고 있는 유기 전계 발광 소자 | |
CN108997201A (zh) | 一种螺芴杂蒽化合物及其有机电致发光器件 | |
CN111533678B (zh) | 高效率电子阻挡材料及使用该种材料的有机电致发光器件 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |