TWI275628B - New compound and organic light emitting device using the same - Google Patents
New compound and organic light emitting device using the same Download PDFInfo
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- TWI275628B TWI275628B TW094133221A TW94133221A TWI275628B TW I275628 B TWI275628 B TW I275628B TW 094133221 A TW094133221 A TW 094133221A TW 94133221 A TW94133221 A TW 94133221A TW I275628 B TWI275628 B TW I275628B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 56
- 239000011368 organic material Substances 0.000 claims abstract description 20
- 239000000126 substance Substances 0.000 claims description 61
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 125000003277 amino group Chemical group 0.000 claims description 13
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 238000002347 injection Methods 0.000 claims description 7
- 239000007924 injection Substances 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical group NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 5
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 5
- 125000004185 ester group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 150000004982 aromatic amines Chemical group 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-M nitrite group Chemical group N(=O)[O-] IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 229910052707 ruthenium Inorganic materials 0.000 claims description 3
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical group O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- 238000005345 coagulation Methods 0.000 claims description 2
- 230000015271 coagulation Effects 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 235000017166 Bambusa arundinacea Nutrition 0.000 claims 1
- 235000017491 Bambusa tulda Nutrition 0.000 claims 1
- 244000061176 Nicotiana tabacum Species 0.000 claims 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims 1
- 244000082204 Phyllostachys viridis Species 0.000 claims 1
- 235000015334 Phyllostachys viridis Nutrition 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000005577 anthracene group Chemical group 0.000 claims 1
- 239000011425 bamboo Substances 0.000 claims 1
- 230000007547 defect Effects 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 150000002926 oxygen Chemical class 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- 229920001187 thermosetting polymer Polymers 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 55
- 239000000463 material Substances 0.000 description 19
- 238000004519 manufacturing process Methods 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 230000005525 hole transport Effects 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- -1 12 mmol) at 4t Substances 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 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 1
- HYGLETVERPVXOS-UHFFFAOYSA-N 1-bromopyrene Chemical compound C1=C2C(Br)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 HYGLETVERPVXOS-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- XQVWYOYUZDUNRW-UHFFFAOYSA-N N-Phenyl-1-naphthylamine Chemical compound C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 XQVWYOYUZDUNRW-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 206010036790 Productive cough Diseases 0.000 description 1
- 241000270666 Testudines Species 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000005264 aryl amine group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- DLIJPAHLBJIQHE-UHFFFAOYSA-N butylphosphane Chemical compound CCCCP DLIJPAHLBJIQHE-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 238000007591 painting process Methods 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 210000003802 sputum Anatomy 0.000 description 1
- 208000024794 sputum Diseases 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
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- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/20—Spiro-condensed ring systems
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- 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
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- C09K2211/10—Non-macromolecular compounds
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- 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
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/1458—Heterocyclic containing sulfur as the only heteroatom
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/1466—Heterocyclic containing nitrogen as the only heteroatom
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- 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
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
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- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Pyridine Compounds (AREA)
- Luminescent Compositions (AREA)
Description
1275628 九、發明說明: 【發明所屬之技術領域】 本發明是關於一創新化合物,由一氟延伸化合物組成,能 顯著的改良壽命、效率及電化學及熱穩定性。 % 【先前技術】 有機發光現象是一有機分子内部程序轉換電流到可見光 ^的例子。有機發光現象是依據以下的_。當有機材料 =與陰極之間時,如果在這兩個電極之間施加電壓,電^ ^ 3=及陰極注入有機材料層。注人到有機材料層的電子 /、电洞、、Ό合而形成激子,激子降低到底層狀態發射 3機制的有機發光裝置典型的含陰極、陽極、及^於^ J機U層⑻,而有機材料層可含有電 電;^ 層、發光層、及電子輸送層。 也/Π輸达 料與娜或有機材 =料、發光材料、電電洞 料报容易還原而且型性質的有機材 材料或電子輸是使料電子注入 型與η-型性質的有機 f/材科;比較需要同時具有p_ 種具有高發光效率:g b^原後都穩^,也需要一 更進一^ 田^子形成時,能將激子轉換成光線。 的性質。、使用在有機發光裝置的材料也最好要有以下 性 1275628 近才用來做電洞輪送層觀,其 此度低於觸c,因 置,盒:有高效率的有機發光裝 不會由發:=== 有., 目前作為有機發光裝置二*、'同於 的LUM0月匕里層, 產,低於使用為發光;ί材^^’使用溶液塗裝方法生 率及長壽命的有機ϋϊϊ的有義材料,因此很難產生有高效 定性而4m錢發紐置的㈣必須要有雛的化學穩 穩^生 屬威物雜魏好齡面來確認裝置的 【發明内容】 有機的是提供錢發光敍—養料能滿足 學穩3的條件,例如’合適的能量層次,電化 行有機料性’ *且含絲化魅物魏學結構能執 仃百触植置所需要的各種角色的替代群。 機材=r 一電極、包括發光層之有 =物機材料層最少有一層含下列化學式1的 化合物 熱硬化或可光交聯群組之具有含化學式1的 1275628 [化學式1]
_ 化學式卜X是C或Si,而A是-NZ1Z2。 Y疋一鍵結,二價芳香烴類;最少被一取代群組取代之二 ,芳香烴類,該取代群組選自硝基、硝酸基、函素、烷基、烷 氧基、及胺基群所組成之群組;二價雜環群;或最少被一取代 群組取代之二價雜環群,該取代群組選自硝基、硝酸基、鹵素、 - 烷基、烷氧基、及胺基群所組成之群組。 _ Z1到Z2各為獨立的氫;含碳數量為1_2〇之脂肪烴類; 芳香烴類;最少被一取代群組取代之芳香烴類,該取代群組選 自1基、硝酸基、_素、烷基、烷氧基、胺基、芳香烴類、及 鲁 #環群所組成之群組;用芳香烴類取代的石夕群;雜環群;最少 被一取=群組取代之雜環群,該取代群組選自硝基、硝酸基、 鹵素、k基、烷氧基、胺基、芳香烴類、及雜環群所組成之群 組;被含碳數量1 — 20的烴類或含碳數量6 - 20的芳香烴類取 代之代苯基群;或被芳香烴類取代的硼群。 、 f RU各為獨立的氫、取代或被取代之烧基群、取代 院ί 3、取代或被取代之縣群、取代或被取代 ϋ n 取代之雜環群、胺基群、石練基群、确 基群、*素群、酼胺群、或酯群。R1到 群組形成祕或雜凝結環。 」‘ 相㈣ 1275628 R12到R15各為獨立的氳、取代或被取代之烷基群,取代 或被取代之烧氧基群,取代或被取代之浠基群,取代或被取代 之芳香基群’取代或被取代之雜環群、胺基群、硝酸基群、硝 基群、鹵素群、醯胺群、或酯群。R12到R15可能會與相鄰的 群組形成脂肪或雜凝結環。 抑R7與R8可以直接的互相連結或可以與一群組形成凝結 % ’此群組逼:自的群組含〇、S、NR、PR、〇〇、CRR,、及
SiRR’。R與R’各為獨立的(或共同為)氯、取代或被取代之 烧基群、、取似被取代之烧氧基群、取代或被取代之烯基群、 取代或被取代之芳香基群、取代或被取代之芳香基胺群、取代 或被取代之雜環群、硝’絲群、胺群、或酯群,及可以形成 一凝結環後再形成一螺形化合物。 化學式1取代群的詳細說明。 1 為巧學式1的取代群,芳香烴類範例為單環芳 =衣妨t ί基、聯苯基、及三苯、及多環芳香族環,如奈基、 =唾基、触基、基、氧二唾基^^基三^、 疋基、°疋基、嗒基、磺安基、及異奎林基。 跡子含_旨_貞、分叉鏈脂 另丁基群、ί 丁基群Γ對·;正丁基群、 的婦基群,如苯乙縣、及三鍵炔基^如m群;有雙鍵 沾^學式1的R1到R15芳香基群說明範例,作τ曰㈣丨从 的,含單環芳香族環’如苯基群、聯苯基群、]三二-=生 !275628 酉分基群、非基群、核 s;群及香族環’如奈基群、 性的,Ri=香胺基群說明範例,但不是限制 三群、二笨基胺群、甲苯絲群、销群、及 含代ϊίί1 ΐΐ1到R15雜環群說明範例,但不是限制性的, 各鱗、硫亞絲群、代錄群、氧嗅 ㈣綱、雜基群、 =外,化學式丨的R1到Ri5的烯基、芳香基、 =禪細範例,但不是限制性的,含下列化學式顯^的群 1275628
在上面的化學式,2是_群其選自的群 1 _20之脂肪烴類、絲基群、芳香基胺群、芳香^群 石肖酸基群、及乙炔群。Z的芳香基胺、芳,環 在上述R1到R11的取代群。 及硪衣群頒不 依f $明一個比較好的組合’化學式】的X是c,而 R7及R8疋直接的互相連結或與-群形錢結環,此群 的??f二 Sn NR、服、C=〇、⑽、及 SlRR,(R 及 R,都 定義在化学式1)。 依據本發明另一個比較好的組合,化學式〗 π八i的X是Si, 而R7及R8是直接的互相連結或與一群形成凝結環,此群組 1275628 =定ms、服、pr、c=〇、⑽、及—及 依據本發明再另外-個比較好的組合,化 是化學式2到5的化合物中的任何一個。 口
m
m:
【化學式3】 【化學式2】 m
R1S 【化學式4】
RS
【化學式5】 在化學式2到5,A如前述定義。 化學式1之A群的說明範例,但不是限制性的,如 結合化學式2到5的化合減下φ的A魏形成各種的街生 11 1275628 化合物。舉例來說,如果化學式2的化合物結合第1群組,產 品將會標示為化學式2-1。 [A群]
1 2 3 4 5 6 7
43 44 4ϊ 46 4F 48
12 1275628
【實施方式】 弟一圖係為一有機發光裝置,其組成為基體1、陽極2、 發光層3、及陰極4;第二圖係說明一有機發光裝置其組成為 基體1、陽極2、電洞注入層5、電洞輸送層6、發光層7、電 子輸送層8、及陰極4。 因此,本發明的細部說明如下。 不同的取代群引用到化學式i核心結構的細節,核心結 f a其中—轉鍵賴射基戦唾辆的齡而臟,如此 ΐίί 1化f物的特性可以適用於有機發光裝置有機材料層 9便用。細卽§兄明如下。 ,為使說明方便,能分成 化學式1化合物的立體核心結 兩部份,A與B,如下面的化學式。 1275628
B
A
以古1化合物立體核心結構中的平面A與平面6在又 单而父’Λ在X點’ A與B部份沒有結合。而且,若在 ,固氮位於三個芳香基群中,則結合侷限在平面B。 化度與能量_隙有很緊密的_。更詳細 ,因度增加時,能量頻間隙降低。如上面的 如上面的說明,在本發明裏,爿
到⑽有大能量頻間隙位置的核心Π,==3 有不同的能量頻間隙。一般來今,妳士3|、/此產生的化合物 頻間隙位置馳蝴f缺容㈣it彳彳有ΐ能量 取代群到有小能量賴祕置的核 =、Β $ ’但是引進 間隙。而且,在本發明中,能引則很難控制能量頻 核心結構能控制化合物的H〇M〇 到R19的 而且,經由引進各種取代群到核心处 2曰 有取代群本質的化合物。例如,二°冓之内’能合成各種 料、電洞輸送層材料、發光層材料、、’的電洞注入層材 生產有機發光裝置時使用,的取代引=子輸运層材料,皆在 滿足每一有機材料層需求的物質。|]核心結構來生回收率 的核心結齡料縣躲構,'帥料 14 Ϊ275628 物代表的取代群因發光裝置的化學式!化合 裝置。 衣乍有低啟動電壓及高光線效率的 是雜芳香(如果f1及Z2 控制HOMO及LUMO能量欠^旦哼以)’則能精確的 機材料的介面特性,因此改良有 子如此將有機材料—交互作用最小化上ί; 祕ίϋ^蝴隙及能量層次,舉例來說,為化學式u 塞口 ,在其中芳香基胺引進到電洞輸送材料戋化^ j & t„ H0M0.537eV, ?;4;*;^ΐ 綠洞輸送層。同時,化學式2_2的化合物的ί 、曰1 运是大於ΝΡΒ的鍵間隙,典型的用為電洞於 它的LUM〇值約是2.黯,算是非常的高 光值Ϊ化合物用作電洞輸送層,它增加構成發 3 i 來防止f子由發光層移_翻輸送層。 改良有機發光裝置的發光效率,如此效率古 =B(H_54ev ’ LUM()23ev ’及能量頻 5 g隙 發明,使用典型的⑽哪光譜計算能量頻 還 而且,化學式1的化合物有穩定的氧化還原特性。氧化 15 1275628 ,穩定性烟cv(旋雌特計)方法 "tίί ί2·2 ^ ^ 性&生而心H。這代表化合物對氧化有極佳的穩定 同因為化學式1的化合物有高的玻璃轉化溫 的熱穩錄。舉例來說,化學式2_2的化合=璃)轉 是131 C,還是高於傳統使用的仰吨:%。〇。這^ 先、穩定性的增加在提供裝置啟動穩定性是很重要的。 壯炉2且1生產有機發光裝置時使用真空沉殿程序或容易塗 ί ί 式1的化合物可以用來形成有機材料層。斑這溶 的範例,但不是關性的,含_塗裝程 :塗墨印刷程序,絹印程序,噴灑程序及滾 斤舉例來說,化學式2_2的化合物對極性溶劑,如二甲苯、 請’有报好的溶解度,這些極性溶劑在生產 :=溶液塗裝,咖來生產這裝置。=在: ϋ lit ’ $用洛液塗裝程序形成的薄膜或_物的發光 f的波長,朋為分子_交互作用。有化 予式1、、、吉構的化合物的波長移動很少。 產物依ΐΐΠ ’將三級醇,醋酸化的芳香基及酮基群反應的 ,物,六祕催储-起加赫成六純狀結構,同時去除 :2,生‘的化合物有螺型結構。上述生產這化合物的步驟 =“、、σ自、工蟄’在生產化學式1的化合物時,任何熟悉這工蓺 的ίί改變生產條件。這生產方法在下面的製作範心有詳二 本發明的有機發光裝置能使用現有的材料及現有的程序 ,只需修改最少一層有機材料層來包含本發明的化合物, 16 1275628 這就是,化學式1的化合物。 依^據本發明’有機發rk p: m. / / , n 結構,或者是替代的,多匕層可以是單-層叠 詹、電洞輪送層、^層t 以包含電祠注入 她从姓居^ ^私千輸达層、及電子注入層作&女 =有;=料,光物 這關聯的可以使^理“沉、及第二電極。與 子線蒸發綠,蚁綠法,如雖方法或電 用化或例子說明生產化學式1的化合物及使 ς作耗例及例子指示用來做制之用,並不是用來限制本發 的化合物 使用以下的製作範例或例子說明生產化學式1 的化合物生產有機發光裝置的方法。然而,以 發明t耗列及例子指示用來做說明之用,並不是用來限制本 了生產化學式1的化合物,可以使用下列任-化合物的 化子式,a到c,作為起始材料。
化學式b
化學式c 17 1275628 製作範例1 :製作化學式a代表的起始材料 將唾(1.672g ’ l〇mm〇i),1·溴 峨苯(1 5ml,12mmol),碳 酸_(1^2(1:03,2.7646g,20mmol),埃化銅(Cul,95mg, 0.5mmol),及25ml二甲苯在氮環境回流。在冷卻到正常溫度 後,用乙酸乙酯萃取產品,用無水硫酸鎂(MgS〇4)去除水,而 溶劑在低壓去除。產生的產品通過矽膠,使用己烷溶劑生產化 合物’溶劑在低壓去除,然後使用真空乾燥生產白色的固體化 馨合物(800mg,25%回收率)。ms : [M+H]+=323。 製作範例2 :製作化學式b代表的起始材料 將4.19g化學式a代表的起始材料(13mm〇1)溶解到純化的 THF,然後慢慢的在_78t輸入4就的η-Βιιυ(2·5Μ己烧溶 液,12mmol)。在同一溫度混合45分鐘,然後加入2 59g的 2-溴-9-氟(l〇.〇mmol)。在同一溫度下混合i小時,溫度回升到 ❿ 正^度’繼續混合2小時。反應在氯化氨(NH4C1)水溶液中 完成,然後用乙_萃取有機材料,然後去除水分,將有機溶劑 去除生產黃色的固體。將固體產品在乙醇中分散,混合,過渡, 然後真空乾燥生產4.5g的中間材料。將中間固體產物在4〇ml 酉曰酉夂中为散’然後加12滴濃縮硫酸,再回流3小時。當達到 正常溫度時,將產品固體過濾,用乙醇清洗,然後真空乾燥來 生產 3.98g 的產品(82·2〇/〇回收率)。MS : [M+H]+=484。 18 1275628 衣作範例3 ·製作化學式c代表的起始材料 將化學式b代表的起始材料(10.0g,n.8mm〇1)完全溶解到 200ml 的 THF,然後加人 4_氯·苯猶(8.3〇g,53 3mm〇1),观 碳酸鉀溶液,烷氧基異丁基異(三苯基膦)鈀⑼(〇62g, 0.53mm〇l),及1_乙醇’再回流24小時。當反應完成後, 冷卻到正常溫度’_。用水及乙騎洗幾次。用乙醇重新結 曰曰,再真空乾燥生產化合物(9.5g,85°/。回收率)。MS : [M+H]+=625 〇 例1 :製作化學式2-2代表的化合物 將化學式b的化合物(3.〇g,6.19mmol)及N-苯基-1-奈基胺 d.5g,6.81mm〇l)溶解到50ml的甲苯,然後加入特丁氧化鈉 (〇.89g,9.3mmol),二(聯苯李登丙酮)鈀⑼(pd(dba)2,〇 〇7g, ai24mm〇1),及 50wt% 三-三級· 丁基膦(0·09πύ,0.186mmol), 然後在氮環境回流2小時。再將蒸餾水加入反應溶劑來完成反 應’然後萃取有機層。使用n_己烷及四氫喃基溶劑己烷 /THF〜4/1)執行柱式分離程序,在乙醇中重新結晶,然後真空 乾文呆來生產化合物(2.0g,回收率52%)。MS : [M+Hf=622。 例2 :製作化學式3_2代表的化合物 將化本式c化合物(5.0g,9.69mmol)及N-苯基-1-奈基胺 (10.5mm〇l)溶解到50ml的曱苯,然後加入特丁氧化納
19 1275628 a〇2g,3umm〇i),二(聯苯李登丙酮)把⑼(pd(dba)2,〇 217g, 〇.121mm〇l),及 50wt% 三-三級_ 丁基膦(〇 13πύ,〇315mm〇1), • 然後在氮環境回流2小時。再將蒸餾水加入反應溶劑來完成反 — 應,然後萃取有機層。使用n_己烷及四氫喃基溶劑(η-己烷 /THF=4/1)執行柱式分離程序,在乙醇中重新結晶,然後真空 乾:^來生產化合物(4.2g,回收率62%)。ms : [M+H]+=698。 例3 :生產有機發光裝置 在玻璃基體(康寧7059玻璃),塗上1000A厚的IT〇(氧化 銦錫)形成薄膜,將其放入溶解有清潔劑的蒸餾水,再用超音 波β洗。與這相關的是,使用FischerInc•製造的清潔劑,蒸餾 水的製造使用Milliporelnc·過濾器過濾兩次。在IT〇清洗3〇 分鐘後,朗超音波在蒸财巾洗兩次。在蒸财清洗完畢 後’用超音波及異丙醇、丙酮、與乙醇溶劑清洗,然後乾燥。 • 了一步將其送到電漿清洗機。使用氧電漿清洗基體5分鐘,然 後送到真空蒸發器。 下面化學式的六硝酸六氮三苯(以後稱為,ΉΑΤ”)在透明 ιτο私極上’用上面的步驟製作,經過真空沉殿形成5〇〇Α薄 膜,如此形成的陽極含有ΙΤ〇導電層及1型有機材料。 20 1275628 [狐η
在帝,化學式厶2的化合物(400人)真空沉澱形成電洞輸送層。 輪送層上真空沉殿厚度300入的Alq3,形成發光層。在 ^上將下面化學式的電子輸送層材料沉殿200人厚度,形 成龟子輪送層。 電子輸送層材料
依序的將厚度12A的氟化鋰(LiF)及厚度2000A的鋁沉澱 到電子輸送層來形成陰極。 在以上的步驟,將有機材料沉澱的速度維持在 〇.3-0.8A/sec。而且,氟化鋰(LiF)及鋁的沉澱到陰極的速度各 自是0.3A/sec及l.5_2.5A/sec。在沉澱時,真空維持在l_3*l(T7。 得到的裝置的電場是9.74V,前進電流密度為 100mA/cm2,及頻率的光效率為i.631m/W。在上述啟動電流的 裝置操作及光發射表示化學式2-2的化合物,在電洞注入層及 1275628 發光層之間形成的層,用來輪送電洞。 例4 :生產有機發光裝置 重複例3步驟生產裝置,不同的是用化學式η的化合物 替代化學式2-2的化合物來作為電洞輸送層。 在Η進電流密度l〇〇mA/cm2 τ,得到的裝置的電場為 8.59V ’而光邊的光線效率為裝置在上述啟動電壓 的操作與光線放射表示化學式3_2的化合物,形成電洞注入^ 薄膜與發光層薄膜之間的中間層,作用為輸入動電洞。曰 本發明的化合物能用為有機材料層材料,特別是,有機發 光^置的電洞注入及/或輸送材料,而且當使用在有機發光^ 置時,它能降低裝置的啟動電壓,因此改良光線效率f^以及 經由化合物的熱穩定性改良裝置的壽命。 【圖式簡單說明】 第一圖係為一有機發光裝置;及 第二圖係說明一有機發光裝置。 符號說明】 土 陽極 電洞注入層 5 發光層 1 電洞輸送層 6 陰極 發光層 η 4 電子輸送層 8 22
Claims (1)
1275628 十、申請專利範圍: 1、一^有機發光裝置,包含: 第一電極; 芦含it有機材料層包括發故,其中最少有—層有機材料 i人式1的化合物或採用可熱硬化或可光交聯群組之具 有S化學式1的化合物;以及 弟一^極; ibl’第一電極,有機材料層與第二電極係形成層疊結構;
其中: X是C或Si ;
A 是 _NZ1Z2 ; Y疋一鍵結,二價芳香烴類;最少被一取代群組取代之二 香烴類,該取代群組係選自硝基、硝酸基、鹵素、烷基、 烷氧基、及胺基群所組成之群組;二價雜環群;或最少被一取 代群組取代之二價雜環群,該取代群組選自硝基、硝酸基、鹵 素、烷基、烷氧基、及胺基群所組成之群組; Ζ1與Ζ2各為獨立的氫;含碳數量為uo之脂肪烴類;芳 香烴類,最少被一取代群組取代之芳香烴類,該取代群組選自 硝基、硝酸基、i素、烧基、烧氧基、胺基、芳香煙類、及雜 環群所組成之群組;用芳香烴類取代的矽群;雜環群;最少被 —取代群組取代之雜環群,該取代群組選自硝基、硝酸基、鹵 1275628 素、烧基、烧氧基、胺基、芳香烴類、及雜環群所組成之群組; 被含礙數量1 - 20的烴類或含碳數量6 - 20的芳香烴類取代之 代苯基群;或被芳香烴類取代的硼群; R1到R11各為獨立的氫、取代或被取代之烷基群、取代或 被取代之烧氧基群、取代或被取代之烯基群、取代或被取代之 - 芳香基群、取代或被取代之雜環群、胺基群、硝酸基群、硝基 群、鹵素群、醯胺群、或酯群;其中,幻到R11可與相鄰的群 組形成脂肪或雜凝結環; R12到R15各為獨立的氫、取代或被取代之烷基群、取代 或巧取代之烷氧基群、取代或被取代之烯基群、取代或被取代 之芳香基群、取代或被取代之雜環群、胺基群、硝酸基群、硝 基群、鹵素群、醯胺群、或酯君羊;其中,R12到R15可與相鄰 的群組形成脂肪或雜凝結環;以及 成R7,與R8可以直接的互相連結或可以與一群組形成凝結 環’此群組运自的群組含Q、S、皿、pR、,、及; ^中’R與R’各為獨立的(或共同為)氫、取代或被取代之烷 基群、、取代或餘代找氧鱗、取代或被取狀烯基群、取 ,或被取代之芳香基群、取代或被取代之芳縣胺群、取代或 衣群、硝酸基群、醯胺群、或酯群,以及可形成-旋、、、^壞後再形成一螺形化合物。 第1項所述之有機發光裝置,其中化學式1 p 14一群形成凝結環,此群選自的群組含〇、S、NR、 、-、CRR’、及SiRR,(R&R,定義在化學式心 疋仕化學式2到5化合物·· 24 1275628 R5
【化學式2】 m
【化學式3】
【化學式4】 【化學式5】
其中,在化學式2到5中,A定義於申請專利範圍第1 項0 4、如申請專利範圍第1項所述之有機發光裝置,其中化學式1 的A為下列群組之一: 25 1275628
26 1275628
ο 27 _ 81 1275628
7所述之有機發光裝置,其中該有機特 竹層3包洞輸达層,而電洞輪 材 可熱硬化財歧料权用
專利範圍第1項所述之有機發光裝置,其中該有機枒 ίί L⑽注人層,而電润注人層含化學式1的化合物或2 可;^硬化或可光交聯群組之具有含化學式丨的化合物。/ 7、如申晴專利範圍第1項所述之有機發光裝置,其中 層含-電洞注入/輸送層,其包含化學式i的化合物或採用可敎 硬化或可光交聯群組之具有含化學式丨的化合物。 …、
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