TW201428085A - 用於有機電致發光裝置的材料 - Google Patents
用於有機電致發光裝置的材料 Download PDFInfo
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- TW201428085A TW201428085A TW102146763A TW102146763A TW201428085A TW 201428085 A TW201428085 A TW 201428085A TW 102146763 A TW102146763 A TW 102146763A TW 102146763 A TW102146763 A TW 102146763A TW 201428085 A TW201428085 A TW 201428085A
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- 239000000463 material Substances 0.000 title claims description 47
- 150000001875 compounds Chemical class 0.000 claims abstract description 128
- 125000003118 aryl group Chemical group 0.000 claims description 76
- 239000000203 mixture Substances 0.000 claims description 55
- 125000004432 carbon atom Chemical group C* 0.000 claims description 42
- -1 NR 2 Inorganic materials 0.000 claims description 35
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 25
- 238000005859 coupling reaction Methods 0.000 claims description 22
- 229920000642 polymer Polymers 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 230000000903 blocking effect Effects 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- 230000008878 coupling Effects 0.000 claims description 16
- 238000010168 coupling process Methods 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
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- 229910052740 iodine Inorganic materials 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 239000000412 dendrimer Substances 0.000 claims description 13
- 229920000736 dendritic polymer Polymers 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 10
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- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 claims description 7
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 6
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
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- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
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- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 4
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- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 4
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- 125000005580 triphenylene group Chemical group 0.000 claims description 4
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 3
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- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 3
- 238000006880 cross-coupling reaction Methods 0.000 claims description 3
- 150000003254 radicals Chemical group 0.000 claims description 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
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- 230000005669 field effect Effects 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 125000004437 phosphorous atom Chemical group 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- 230000000171 quenching effect Effects 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims description 2
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- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- 230000004936 stimulating effect Effects 0.000 claims 1
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 22
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- 238000003786 synthesis reaction Methods 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 13
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
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- 238000010992 reflux Methods 0.000 description 12
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- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 239000002019 doping agent Substances 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 125000003003 spiro group Chemical group 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
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- 125000005842 heteroatom Chemical group 0.000 description 7
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 7
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- 230000004888 barrier function Effects 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical class [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 5
- 238000007639 printing Methods 0.000 description 5
- 229910052707 ruthenium Inorganic materials 0.000 description 5
- 238000007740 vapor deposition Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
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- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
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- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
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- 235000011152 sodium sulphate Nutrition 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 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
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 3
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- 238000006887 Ullmann reaction Methods 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
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- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
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- 125000005259 triarylamine group Chemical group 0.000 description 3
- PSZXPGFNGPBEFR-UHFFFAOYSA-N trisodium butan-1-olate Chemical compound [Na+].[Na+].[Na+].CCCC[O-].CCCC[O-].CCCC[O-] PSZXPGFNGPBEFR-UHFFFAOYSA-N 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical class C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 2
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- USYQKCQEVBFJRP-UHFFFAOYSA-N 1-bromo-3-phenylbenzene Chemical group BrC1=CC=CC(C=2C=CC=CC=2)=C1 USYQKCQEVBFJRP-UHFFFAOYSA-N 0.000 description 2
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- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 2
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- VIHDTGHDWPVSMM-UHFFFAOYSA-N ruthenium;triphenylphosphane Chemical compound [Ru].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 VIHDTGHDWPVSMM-UHFFFAOYSA-N 0.000 description 1
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- 238000002061 vacuum sublimation Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Classifications
-
- 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
-
- 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
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
-
- 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
- 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
- C07D209/96—Spiro-condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
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Abstract
本發明係關於適用於電子裝置中之化合物,及包含此等化合物之電子裝置(特定言之有機電致發光裝置)。
Description
本發明係關於用於電子裝置(特定言之有機電致發光裝置)之材料,及包含此等材料之電子裝置(特定言之有機電致發光裝置)。
其中使用有機半導體作為功能材料之有機電致發光裝置(OLED)之結構係描述在(例如)US 4539507、US 5151629、EP 0676461及WO 98/27136中。此處所使用的發射材料係使用得越來越多的呈現磷光而非螢光的有機金屬錯合物。由於量子力學上的原因,使用有機金屬化合物作為磷光發射體可使能量及功率效率提升高達四倍。然而,一般而言,仍需要改良OLED(尤其還有呈現三重態發射(磷光現象)之OLED)之(例如)效率、操作電壓及壽命。
磷光OLED之性質不僅係由所使用的三重態發射體決定。特定言之,所使用的其他材料(諸如基質材料、電洞阻擋材料、電子傳遞材料、電洞傳遞材料及電子或激子阻擋材料)在此處亦特別重要。因此,此等材料之改良亦可導致OLED的性質的顯著改良。
根據先前技術,尤其使用吲哚并咔唑衍生物(例如根據WO 2007/063754或WO 2008/056746)、茚并咔唑衍生物(例如根據WO 2010/136109)或茀或螺二茀衍生物(例如根據WO 2012/074210)作為有機電致發光裝置中之磷光發射體之基質材料。此處希望進一步改良(特定言之)該等材料之效率、壽命及熱安定性。
本發明之目標係提供適合在OLED中(特定言之)作為磷光發射體
之基質材料,而且作為電洞阻擋材料、作為電子傳遞材料或視需要作為電洞傳遞及/或電子阻擋材料使用之化合物。本發明之另一目標係提供用於有機電致發光裝置之其他有機半導體,以便為熟習此項技術者製造OLED提供更多可供選擇的材料。
出乎意料的是,已發現,下文中更詳細描述的某些化合物可達成此目標,其等非常適用於OLED,並導致有機電致發光裝置的改良。此處的改良係關於(特定言之)壽命及/或操作電壓。因此,本發明係關於此等化合物及包含此類化合物之電子裝置(特定言之有機電致發光裝置)。
本發明係關於式(1)或式(1A)化合物,
其中以下內容適用於所使用的符號及下標:Y在每次出現時相同或不同地為CR1或N,限制條件係至少一個基團Y表示N;X在每次出現時相同或不同地為CR1或N;或兩個相鄰X表示S、O或NR1,以便形成五員環形式;或兩個相鄰X表示下式(2)、(3)或(4)基團,
其中^指示式(1)中相應相鄰基團X;V在每次出現時相同或不同地為C(R1)2、NR1、O、S、BR1、Si(R1)2或C=O;Z在每次出現時相同或不同地為CR1或N;Ar在每次出現時相同或不同地為具有5至40個芳族環原子之芳族或雜芳族環系統,其可經一或多個基團R1取代;R在每次出現時相同或不同地選自由下列組成之群:H、D、F、Cl、Br、I、CN、N(Ar1)2、具有1至40個C原子之直鏈烷基或具有3至40個C原子之分支鏈或環狀烷基(其中各者可經一或多個基團R2取代,其中一或多個非相鄰CH2基團可經R2C=CR2、C≡C或O置換,且其中一或多個H原子可經D或F置換)、或具有6至60個芳族環原子之芳族環系統(其可經一或多個基團R2取代);此處的兩個相鄰取代基R可形成單環或多環脂族或芳族環系統,其可經一或多個基團R2取代;R1在每次出現時相同或不同地選自由下列組成之群:H、D、F、Cl、Br、I、CN、NO2、N(Ar1)2、N(R2)2、C(=O)Ar1、C(=O)R2、P(=O)(Ar1)2、P(Ar1)2、B(Ar1)2、Si(Ar1)3、Si(R2)3、具有1至40個C原子之直鏈烷基、烷氧基或硫烷基、或具有3至40個C原子之分支鏈或環狀烷基、烷氧基或硫烷基、或具有2至40個C原子之烯基或炔基(其中各者可經一或多個基團R2取代,其中一或多個非相鄰CH2基團可經R2C=CR2、C≡C、Si(R2)2、C=O、C=S、C=NR2、P(=O)(R2)、SO、SO2、NR2、O、S或CONR2置換,且其中一或多個H原子可經D、F、Cl、Br、I、CN或NO2置換)、具有5至60個芳族環原子之芳族或雜芳族環系統(其在每次出現時可經一或多個基團R2取代)、具有5至60個芳族環原子之芳氧基或雜芳氧基(其可經一或多個基團R2取代);此處的兩個相鄰取代基R1可視需要形成單環或多環脂族、芳族或雜芳族環系統,其可經一或多個基團R2取代;
Ar1在每次出現時相同或不同地為具有5-30個芳族環原子之芳族或雜芳族環系統,其可經一或多個非芳族基團R2取代;此處鍵合至同一N原子或P原子之兩個基團Ar1亦可藉由單鍵或選自N(R2)、C(R2)2、O或S之橋彼此橋接在一起;R2在每次出現時相同或不同地選自由下列組成之群:H、D、F、CN、具有1至20個C原子之脂族烴基、或具有5至30個芳族環原子之芳族或雜芳族環系統(其中一或多個H原子可經D、F、Cl、Br、I或CN置換),其中兩個或更多個相鄰取代基R2可相互形成單環或多環脂族環系統;m、n在每次出現時相同或不同地為0或1,限制條件係m+n1;p在每次出現時相同或不同地為0、1、2、3或4;q係0、1或2。
本發明意義下的芳基含有6至60個C原子;本發明意義下的雜芳基含有2至60個C原子及至少一個雜原子,限制條件係C原子及雜原子之總數為至少5。該等雜原子較佳係選自N、O及/或S。此處的芳基或雜芳基意指簡單芳族環(亦即苯)或簡單雜芳族環(例如吡啶、嘧啶、噻吩等)或縮合(稠合)芳基或雜芳基(例如萘、蒽、菲、喹啉、異喹啉等)。相比之下,藉由單鍵相互鍵聯在一起的芳族基(諸如,例如,聯苯)並不稱為芳基或雜芳基,而稱為芳族環系統。
本發明意義下的芳族環系統係在該環系統中含有6至60個C原子。本發明意義下的雜芳環系統係在該環系統中含有2至60個C原子及至少一個雜原子,限制條件係C原子及雜原子之總數為至少5。該等雜原子較佳係選自N、O及/或S。就本發明之目的而言,芳族或雜芳族環系統意指不一定僅含有芳基或雜芳基之系統,相反地,除此之外,在該系統中,複數個芳基或雜芳基可藉由非芳族單元(諸如,例如,C、N或O原子)連接在一起。因此,就本發明之目的而言,例
如,諸如茀、9,9‘-螺二茀、9,9-二芳基茀、三芳基胺、二芳基醚、二苯乙烯等系統亦意欲理解為芳族環系統,其中兩個或更多個芳基係藉由(例如)短烷基連接在一起之系統亦然。
就本發明之目的而言,可含有1至40個C原子,且除此之外,其中個別H原子或CH2基團可經上述基團取代之脂族烴基或烷基或烯基或炔基較佳意指以下基團:甲基、乙基、正丙基、異丙基、正丁基、異丁基、第二丁基、第三丁基、2-甲基丁基、正戊基、第二戊基、新戊基、環戊基、正己基、新己基、環己基、正庚基、環庚基、正辛基、環辛基、2-乙基己基、三氟甲基、五氟乙基、2,2,2-三氟乙基、乙烯基、丙烯基、丁烯基、戊烯基、環戊烯基、己烯基、環己烯基、庚烯基、環庚烯基、辛烯基、環辛烯基、乙炔基、丙炔基、丁炔基、戊炔基、己炔基、庚炔基或辛炔基。具有1至40個C原子之烷氧基較佳意指甲氧基、三氟甲氧基、乙氧基、正丙氧基、異丙氧基、正丁氧基、異丁氧基、第二丁氧基、第三丁氧基、正戊氧基、第二戊氧基、2-甲基丁氧基、正己氧基、環己氧基、正庚氧基、環庚氧基、正辛氧基、環辛氧基、2-乙基己氧基、五氟乙氧基及2,2,2-三氟乙氧基。具有1至40個C原子之硫烷基意指(特定言之)甲基硫基、乙基硫基、正丙基硫基、異丙基硫基、正丁基硫基、異丁基硫基、第二丁基硫基、第三丁基硫基、正戊基硫基、第二戊基硫基、正己基硫基、環己基硫基、正庚基硫基、環庚基硫基、正辛基硫基、環辛基硫基、2-乙基己基硫基、三氟甲基硫基、五氟乙基硫基、2,2,2-三氟乙基硫基、乙烯基硫基、丙烯基硫基、丁烯基硫基、戊烯基硫基、環戊烯基硫基、己烯基硫基、環己烯基硫基、庚烯基硫基、環庚烯基硫基、辛烯基硫基、環辛烯基硫基、乙炔基硫基、丙炔基硫基、丁炔基硫基、戊炔基硫基、己炔基硫基、庚炔基硫基或辛炔基硫基。一般而言,根據本發明之烷基、烷氧基或硫烷基可係直鏈、分支鏈或環狀,其中一或多個
非相鄰CH2基團可經上述基團置換;此外,一或多個H原子亦可經D、F、Cl、Br、I、CN或NO2(較佳F、Cl或CN,更佳F或CN,特別佳CN)置換。
具有5-60個芳族環原子之芳族或雜芳族環系統(其亦可在每次出現時經上述基團R2或烴基取代,且其可經由任何所需位置鍵聯於芳族或雜芳族環系統上)意指(特定言之)衍生自苯、萘、蒽、苯并蒽、菲、芘、(chrysene)、苝、丙二烯合茀、稠四苯、稠五苯、苯并芘、聯苯、亞聯苯、聯三苯、三亞苯、茀、螺二茀、二氫菲、二氫芘、四氫茲、順式-或反式-茚并茀、順式-或反式-茚并咔唑、順式-或反式-吲哚并咔唑、參茚并苯、異參茚并苯、螺參茚并苯、螺異參茚并苯、呋喃、苯并呋喃、異苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、異苯并噻吩、二苯并噻吩、吡咯、吲哚、異吲哚、咔唑、吡啶、喹啉、異喹啉、吖啶、菲啶、苯并-5,6-喹啉、苯并-6,7-喹啉、苯并-7,8-喹啉、吩噻嗪、吩噁嗪、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑、菲并咪唑、吡啶并咪唑(pyridimidazole)、吡嗪并咪唑(pyrazinimidazole)、喹噁啉并咪唑、噁唑、苯并噁唑、萘并噁唑、蒽并噁唑、菲并噁唑、異噁唑、1,2-噻唑、1,3-噻唑、苯并噻唑、噠嗪、六氮雜三亞苯、苯并噠嗪、嘧啶、苯并嘧啶、喹噁啉、1,5-二氮雜蒽、2,7-二氮雜芘、2,3-二氮雜芘、1,6-二氮雜芘、1,8-二氮雜芘、4,5-二氮雜芘、4,5,9,10-四氮雜苝、吡嗪、吩嗪、吩噁嗪、吩噻嗪、熒紅環(fluorubin)、萘啶、氮雜咔唑、苯并咔啉、菲咯啉、1,2,3-三唑、1,2,4-三唑、苯并三唑、1,2,3-噁二唑、1,2,4-噁二唑、1,2,5-噁二唑、1,3,4-噁二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、1,3,5-三嗪、1,2,4-三嗪、1,2,3-三嗪、四唑、1,2,4,5-四嗪、1,2,3,4-四嗪、1,2,3,5-四嗪、嘌呤、蝶啶、吲嗪及苯并噻二唑之基團或衍生自此等系統之組合之基團。
本申請案意義下的相鄰基團或相鄰取代基意指鍵合至C原子(其進一步相互直接鍵合在一起)之取代基或鍵合至同一C原子之取代基。
在本發明之一較佳實施例中,X在每次出現時相同或不同地表示CR1或N,其中每環中最多一個基團X表示N;或兩個相鄰基團X表示式(2)或(3)(特定言之式(3))基團,其中Z在每次出現時相同或不同地表示CR1,且V在每次出現時相同或不同地表示NR1、C(R1)2、O或S。此外較佳地,存在於X上之相鄰基團R1不會相互形成環。特別佳地,X在每次出現時相同或不同地表示CR1。
式(1)化合物之較佳實施例係下式(5)至(11)化合物,且式(1A)化合物之較佳實施例係下式(12)化合物,
其中所使用的該等符號及下標具有上文所給定的含義。此處的V較佳表示NR1、C(R1)2、O或S。就V=C(R1)2而言,該等兩個基團R1較佳彼此形成環,且因此形成螺系統。
在本發明之一較佳實施例中,p在每次出現時相同或不同地為0、1或2,特別佳0或1及極特別佳等於0。
此外較佳地,q等於0或1,特別佳等於0。
式(5)至(12)結構之特別佳實施例係式(5a)至(12a)結構,
其中所使用的該等符號及下標具有上文所給定的含義。
在本發明之一較佳實施例中,R在每次出現時相同或不同地選自由下列組成之群:H、F、CN、N(Ar1)2、具有1至10個C原子之直鏈烷基或具有3至10個C原子之分支鏈或環狀烷基或具有6至30個芳族環原子之芳族環系統(其可經一或多個非芳族基團R2取代)。在本發明之一特別佳實施例中,R在每次出現時相同或不同地選自由下列組成之群:H、具有1至4個C原子之直鏈烷基或具有3至8個C原子之分支鏈或環狀烷基,特定言之係H。若使用本發明化合物作為製造聚合物之單體,則兩個取代基R亦可較佳表示Br或I,且聚合作用亦可較佳經由此等基團進行。
在本發明之另一較佳實施例中,R1在每次出現時相同或不同地選自由下列組成之群:H、D、F、Br、CN、N(Ar1)2、C(=O)Ar1、P(=O)(Ar1)2、具有1至10個C原子之直鏈烷基或烷氧基或具有3至10個C原子之分支鏈或環狀烷基或烷氧基或具有2至10個C原子之烯基或炔基(其中各者可經一或多個基團R2取代,其中一或多個非相鄰CH2基團可經O置換,且其中一或多個H原子可經D或F置換)、具有5至30個芳族環原子之芳族或雜芳族環系統(其在每次出現時可經一或多個基團R2取代)。R1特別佳在每次出現時相同或不同地選自由下列組成之
群:H、N(Ar1)2、具有1至4個C原子之直鏈烷基或具有3至8個C原子之分支鏈或環狀烷基(其中各者可經一或多個基團R2取代)或具有5至18個芳族環原子之芳族或雜芳族環系統(其在每次出現時可經一或多個基團R2取代)。
若R表示芳族環系統或若R1表示芳族或雜芳族環系統,則該R或R1較佳在每次出現時相同或不同地選自與下文針對Ar所指示的適宜基團相同的基團。
在藉由真空蒸發加工的化合物中,該等烷基較佳具有不多於五個C原子,特別佳不多於4個C原子,極特別佳不多於1個C原子。就自溶液加工的化合物而言,適宜的化合物亦係彼等經具有至多10個C原子之烷基(特定言之分支鏈烷基)取代者或經寡聚伸芳基(例如鄰-、間-、對-或分支鏈聯三苯基或四聯苯基)取代者。
在本發明之一較佳實施例中,n=1且m=0。在本發明之另一較佳實施例中,n=0且m=1。在本發明之又另一較佳實施例中,n=m=1。
較佳基團Ar係具有5至24個芳族環原子之芳族或雜芳族環系統,其在每次出現時可經一或多個基團R1取代。適宜基團Ar係選自苯、鄰-、間-或對-聯苯、鄰-、間-、對-或分支鏈聯三苯、鄰-、間-、對-或分支鏈四聯苯、1-、2-或3-茀基、1-、2-、3-或4-螺二茀基、1-或2-萘基、吡咯、呋喃、噻吩、吲哚、苯并呋喃、苯并噻吩、1-、2-或3-咔唑、1-、2-或3-二苯并呋喃、1-、2-或3-二苯并噻吩、茚并咔唑、吲哚并咔唑、2-、3-或4-吡啶、2-、4-或5-嘧啶、吡嗪、噠嗪、三嗪、蒽、菲、三亞苯、芘、苯并蒽或此等基團中之二者或三者之組合,其中各者可經一或多個基團R1取代。Ar特別佳表示芳族環系統,特定言之選自由下列組成之群:苯、鄰-、間-或對-聯苯、鄰-、間-、對-或分支鏈聯三苯及鄰-、間-、對-或分支鏈四聯苯。若如下文更詳細描述的基團(Het-Ar)亦鍵合至基團Ar(亦即若n=m=1),則基團(Het-
Ar)係鍵合至Ar之任何所需位置。
在本發明之一較佳實施例中,Ar係芳族環系統(亦即不含雜芳基)。此適用於若n=1且如下文所述基團(Het-Ar)亦鍵合至Ar之情形,且亦適用於n=0之情形。
在本發明之另一較佳實施例中,若Ar含有多於一個芳基,則基團Ar中之芳族基並非對位-鍵聯,亦即其等較佳不為對-聯苯、對-聯三苯或對-四聯苯,而為(例如)各自的鄰位-或間位-鍵聯結構。
若Ar含有咔唑、吡咯、咪唑或苯并咪唑基團,則該基團此外較佳不經由氮原子而是經由碳原子鍵聯至Ar之其他芳族單元或鍵聯至氮原子。
就n=1而言,本發明化合物包含具有下式之雜芳基(其在下文中簡寫為(Het-Ar)):
就n=1而言,此基團係存在於本發明化合物中,且就m=1而言係鍵合至Ar,或就m=0而言鍵合至氮。基團(Het-Ar)中之至少一個基團Y及較佳最多三個基團Y表示N,且其他基團Y表示CR1。
較佳實施例係下式(Het-Ar-1)至(Het-Ar-10)基團,
其中虛線鍵結表示至Ar之鍵結,或就m=0而言表示至氮之鍵結,且所使用的該等符號具有上文所給定的含義。
以下式(Het-Ar-1a)至(Het-Ar-10b)基團特別佳,
其中虛線鍵結表示至Ar之鍵結,或就m=0而言表示至氮之鍵結,且所使用的該等符號具有上文所給定的含義。
若(Het-Ar)表示基團(Het-Ar-1)或(Het-Ar-1a),則此基團中之兩個取代基R1較佳表示具有5至24個芳族環原子之芳族或雜芳族環系統(其可經一或多個基團R2取代),特定言之表示苯基、鄰-、間-或對-聯苯、鄰-、間-、對-或分支鏈聯三苯、鄰-、間-、對-或分支鏈四聯苯、1-、2-、3-或4-茀、1-、2-、3-或4-螺二茀、1-、2-、3-或4-二苯并呋喃或1-、2-、3-或4-咔唑。
若(Het-Ar)表示基團(Het-Ar-2)至(Het-Ar-10)或(Het-Ar-2a)至(Het-Ar-10a),則此等基團中之R1較佳在每次出現時相同或不同地表示H、D或具有5至24個芳族環原子之芳族或雜芳族環系統(其可經一或多個
基團R2取代),特定言之表示H或苯基、鄰-、間-或對-聯苯、鄰-、間-、對-或分支鏈聯三苯或鄰-、間-、對-或分支鏈四聯苯。
上述較佳實施例可視需要相互組合在一起。在本發明之一特別佳實施例中,上述較佳項係同時出現。
若將式(1)化合物或該等較佳實施例用作磷光發射體之基質材料或用於直接比鄰磷光層之層中,則該化合物此外較佳不含其中多於兩個六員環係相互直接縮合在一起的縮合芳基或雜芳基。特定言之,基團R、R1、R2及Ar較佳不含其中兩個或更多個六員環係相互直接縮合在一起的芳基或雜芳基,且兩個相鄰基團X較佳不表示式(2)基團。
根據上文所指示實施例之較佳化合物之實例係顯示於下表中之化合物。
本發明化合物之基本結構係可藉由流程圖1中所概述的途徑製備。官能化作用係可根據流程圖2進行。
此處的合成通常係自文獻資料中已知的4-溴螺二茀(Organic Letters 2009,11(12),2607-2610)或經相應取代的4-溴螺二茀開始進行。使該物質與鄰-鹵化胺基苯在C-N偶合反應((例如)使用Pd或Cu催化作用)中反應,其中鹵素較佳係Cl、Br或I。可完全類似地使用(例如)萘、茀、二苯并呋喃或二苯并噻吩衍生物,從而得到含有式(2)或(3)基團之化合物。用以得到相應咔唑衍生物之閉環作用係藉由分子內Pd-催化偶合反應進行。
可自文獻資料中已知的4,4'-二溴螺二茀開始,完全類似地進行式(1A)化合物之合成。
其中n=0且m=1之式(1)化合物係藉由與經相應官能化的芳族化合物或雜芳族化合物(其中反應基較佳係Cl、Br或I)之偶合反應(例如哈特維希-布赫瓦爾德(Hartwig-Buchwald)偶合或烏爾曼(Ullmann)偶合)來獲得。
其中n=1且m=0之式(1)化合物係藉由與經相應離去基團(特定言之Cl或Br)取代之基團(Het-Ar)之親核芳族取代反應或Pd-催化偶合反應來獲得。
其中n=1且m=1之式(1)化合物係藉由與經雙官能化之芳族化合物或雜芳族化合物(其中反應基較佳係溴基及碘基)之偶合反應(例如哈特維希-布赫瓦爾德偶合或烏爾曼偶合)且隨後在使鹵素基團轉化為酸衍生物後視需要進行Pd-催化偶合反應(例如鈴木(Suzuki)偶合、根岸
(Negishi)偶合、山本(Yamamoto)偶合、格利雅交叉(Grignard-Cross)或斯蒂爾(Stille)偶合)來獲得。
此外,本發明係關於一種製備式(1)或(1A)化合物之方法,其包括以下反應步驟:a)合成尚未含基團(Het-Ar)及/或Ar之化合物(1)或(1A)之骨架;及b)使該來自a)之骨架在C-C偶合(諸如鈴木偶合、根岸偶合、山本偶合、格利雅交叉偶合或斯蒂爾偶合等)或C-N偶合(諸如布赫瓦爾德偶合或烏爾曼偶合)中反應。
上述本發明化合物(特定言之經反應性離去基團(諸如溴、碘、氯、酸或酸酯),或經反應性可聚合基團(諸如烯烴、苯乙烯類、丙烯酸酯類或氧雜環丁烷)取代的化合物)可用作生成相應寡聚物、樹枝狀聚合物或聚合物之單體。此處的寡聚作用或聚合作用較佳係經由鹵素官能基或酸官能基或經由可聚合基團進行。此外,可經由此類基團使該等聚合物交聯。本發明化合物及聚合物可用作交聯或非交聯層。
因此,本發明此外係關於含有一或多種上文所指示的本發明化合物之寡聚物、聚合物或樹枝狀聚合物,其中本發明化合物至聚合物、寡聚物或樹枝狀聚合物之一或多個鍵結係存在於一或多個位置而非取代基上。端看本發明化合物之鍵聯,此會形成寡聚物或聚合物之側鏈,或鍵聯於主鏈上,或形成樹枝狀聚合物之核心。該等聚合物、寡聚物或樹枝狀聚合物可係共軛、部分共軛或非共軛。該等寡聚物或聚合物可係直鏈、分支鏈或樹枝狀。與上文所述相同的較佳項適用於寡聚物、樹枝狀聚合物及聚合物中之本發明化合物之重複單元。
就製備該等寡聚物或聚合物而言,使本發明單體與其他單體均聚或共聚。以其中式(1)單元或上文所指示的較佳實施例係以0.01至
99.9莫耳%,較佳5至90莫耳%,特別佳20至80莫耳%之程度存在之均聚物或共聚物較佳。形成聚合物主鏈之適宜且較佳的共聚單體係選自茀(例如根據EP 842208或WO 2000/22026)、螺二茀(例如根據EP 707020、EP 894107或WO 2006/061181)、對-伸苯基(例如根據WO 92/18552)、咔唑(例如根據WO 2004/070772或WO 2004/113468)、噻吩(例如根據EP 1028136)、二氫菲(例如根據WO 2005/014689)、順式-反式-茚并茀(例如根據WO 2004/041901或WO 2004/113412)、酮(例如根據WO 2005/040302)、菲(例如根據WO 2005/104264或WO 2007/017066)亦或複數個此等單元。該等聚合物、寡聚物及樹枝狀聚合物亦可包含其他單元,例如電洞傳遞單元(特定言之彼等基於三芳基胺者)及/或電子傳遞單元。此外,該等聚合物可包含經共聚化或經混合作為摻合物之三重態發射體。特定言之,本發明寡聚物、聚合物或樹枝狀聚合物與三重態發射體之組合產生特別佳結果。
就藉由(例如)旋塗或印刷製程自液相加工本發明混合物而言,本發明化合物之調配物係必需。此等調配物可係(例如)溶液、分散液或乳液。為此,較佳可使用兩種或更多種溶劑之混合物。適宜且較佳的溶劑係(例如)甲苯、苯甲醚、鄰二甲苯、間二甲苯或對二甲苯、苯甲酸甲酯、三甲苯、四氫化萘、藜蘆醚、THF、甲基-THF、THP、氯苯、二噁烷、苯氧基甲苯(特定言之3-苯氧基甲苯)、(-)-葑酮、1,2,3,5-四甲基苯、1,2,4,5-四甲基苯、1-甲基萘、2-甲基苯并噻唑、2-苯氧基乙醇、2-吡咯烷酮、3-甲基苯甲醚、4-甲基苯甲醚、3,4-二甲基苯甲醚、3,5-二甲基苯甲醚、苯乙酮、α-萜品醇、苯并噻唑、苯甲酸丁酯、異丙苯、環己醇、環己酮、環己基苯、十氫萘、十二烷基苯、苯甲酸乙酯、茚滿、苯甲酸甲酯、NMP、對異丙基甲苯、苯乙醚、1,4-二異丙基苯、二芐醚、二乙二醇丁基甲基醚、三乙二醇丁基甲基醚、二乙二醇二丁基醚、三乙二醇二甲基醚、二乙二醇單丁基
醚、三丙二醇二甲基醚、四乙二醇二甲基醚、2-異丙基萘、戊基苯、己基苯、庚基苯、辛基苯、1,1-雙(3,4-二甲基苯基)乙烷或此等溶劑之混合物。
因此,本發明此外係關於一種包含本發明化合物及至少一種其他化合物之調配物。該其他化合物可係(例如)溶劑,特定言之上述溶劑中之一者或此等溶劑之混合物。然而,該其他化合物亦可係至少一種同樣用於電子裝置中之其他有機或無機化合物,例如發射化合物及/或其他基質材料。適宜的發射化合物及其他基質材料係指示於關於有機電致發光裝置的下文中。此其他化合物亦可係聚合物。
本發明化合物係適用於電子裝置,特定言之用於有機電致發光裝置。
因此,本發明此外係關於本發明化合物在電子裝置,特定言之在有機電致發光裝置中之用途。
本發明此外又關於一種包含至少一種本發明化合物之電子裝置。
本發明意義下的電子裝置係包含至少一個包含至少一種有機化合物之層之裝置。該組件亦可包含無機材料或完全由無機材料構建之層。
該電子裝置較佳係選自由下列組成之群:有機電致發光裝置(OLED)/有機積體電路(O-IC)、有機場效電晶體(O-FET)、有機薄膜電晶體(O-TFT)、有機發光電晶體(O-LET)、有機太陽能電池(O-SC)、染料敏化有機太陽能電池(DSSC)、有機光學偵測器、有機光感受器、有機場淬滅裝置(O-FQD)、發光電化學電池(LEC)、有機雷射二極體(O-雷射)及「有機電漿子發射裝置」,但較佳係有機電致發光裝置(OLED),特別佳係磷光OLED。
有機電致發光裝置包含陰極、陽極及至少一個發射層。除該等
層以外,其亦可包含其他層,例如在各情形下,包含一或多個電洞注入層、電洞傳遞層、電洞阻擋層、電子傳遞層、電子注入層、激子阻擋層、電子阻擋層及/或電荷產生層。亦可在兩個發射層之間引入具有(例如)激子阻擋功能之中間層。然而,應指出的是,此等層之各者不一定必須存在。此處的有機電致發光裝置可包含一個發射層,或其可包含複數個發射層。若存在複數個發射層,則此等層在380nm與750nm之間較佳總共具有複數個發射最大值,從而總體上產生白色發射,亦即該等發射層中使用各種可發螢光或發磷光之發射化合物。以具有三個發射層(其中該等三層呈現藍色、綠色及橙色或紅色發射)之系統特別佳(關於基本結構,參見,例如,WO 2005/011013)。本發明有機電致發光裝置亦可係串列式OLED,特定言之亦係白色發射OLED。
根據上文所指示實施例之本發明化合物可用於各種層中,視確切結構而定。較佳是用在有機電致發光裝置,其包含式(1)化合物或上文所指示的較佳實施例作為基質材料,以用於磷光或螢光發射體(特定言之磷光發射體),及/或在電子阻擋或激子阻擋層中及/或在電洞傳遞層中及/或在電洞阻擋層中及/或在電洞阻擋或電子傳遞層中,視確切取代而定。
在本發明之一較佳實施例中,本發明化合物係用作發射層中之磷光化合物之基質材料。此處的有機電致發光裝置可包含一個發射層,或其可包含複數個發射層,其中至少一個發射層包含至少一種本發明化合物作為基質材料。
若本發明化合物係用作發射層中之磷光化合物之基質材料,則其較佳與一或多種磷光材料(三重態發射體)組合使用。本發明意義下的磷光現象意指來自具有相對高自旋多重度(亦即自旋態>1)之激發態(特定言之激發三重態)之冷光。在本申請案意義上而言,所有含過渡
金屬或鑭系元素之發光錯合物(特定言之所有的銥、鉑及銅錯合物)均可視為磷光化合物。
基於包含發射體及基質材料之全體混合物計,本發明化合物及該發射化合物之混合物包含在99與1體積%之間,較佳在98與10體積%之間,特別佳在97與60體積%之間,尤其在95與80體積%之間的本發明化合物。相應地,基於包含發射體及基質材料之全體混合物計,該混合物包含在1與99體積%之間,較佳在2與90體積%之間,特別佳在3與40體積%之間,尤其在5與20體積%之間的該發射體。
本發明之另一較佳實施例係本發明化合物與其他基質材料之組合作為磷光發射體之基質材料之用途。可與本發明化合物組合使用之特別適宜的基質材料係芳族酮、芳族膦氧化物或芳族亞碸或碸(例如根據WO 2004/013080、WO 2004/093207、WO 2006/005627或WO 2010/006680)、三芳基胺、咔唑衍生物(例如CBP(N,N-雙咔唑基聯苯)或WO 2005/039246、US 2005/0069729、JP 2004/288381、EP 1205527、WO 2008/086851或WO 2013/041176中所揭示的咔唑衍生物)、吲哚并咔唑衍生物(例如根據WO 2007/063754或WO 2008/056746)、茚并咔唑衍生物(例如根據WO 2010/136109、WO 2011/000455、WO 2013/041176或WO 2013/056776)、氮雜咔唑衍生物(例如根據EP 1617710、EP 1617711、EP 1731584、JP 2005/347160)、雙極性基質材料(例如根據WO 2007/137725)、矽烷(例如根據WO 2005/111172)、氮雜硼雜環戊烯或酸酯(例如根據WO 2006/117052)、三嗪衍生物(例如根據WO 2007/063754、WO 2008/056746、WO 2010/015306、WO 2011/057706、WO 2011/060859或WO 2011/060877)、鋅錯合物(例如根據EP 652273或WO 2009/062578)、二氮雜噻咯或四氮雜噻咯衍生物(例如根據WO 2010/054729)、二氮雜磷唑衍生物(例如根據WO 2010/054730)、橋聯
咔唑衍生物(例如根據WO 2011/042107、WO 2011/060867、WO 2011/088877及WO 2012/143080)或三亞苯衍生物(例如根據WO 2012/048781)。該混合物中亦可存在比實際發射體在更短波長下發射之其他磷光發射體作為共主體,或存在如(例如)WO 2010/108579中所述在很大程度上不參與電荷傳遞(若參與的話)之化合物。
特定言之,適宜的磷光化合物(=三重態發射體)係在適當激發時發射(較佳)可見區內之光,且除此之外含有至少一種原子序數大於20,較佳大於38且小於84,特別佳大於56且小於80之原子(特定言之具有該原子序數之金屬)之化合物。所使用的磷光發射體較佳係含銅、鉬、鎢、錸、釕、鋨、銠、銥、鈀、鉑、銀、金或銪之化合物,特定言之係含銥或鉑之化合物。
上述發射體之實例係由以下申請案所揭示:WO 00/70655、WO 2001/41512、WO 2002/02714、WO 2002/15645、EP 1191613、EP 1191612、EP 1191614、WO 2005/033244、WO 2005/019373、US 2005/0258742、WO 2010/086089、WO 2011/157339、WO 2012/007086、WO 2012/163471、WO 2013/000531及WO 2013/020631。亦適宜的係(例如)未公開申請案EP 12005187.5及EP 12005715.3中所揭示的金屬錯合物。一般而言,如根據先前技術用於磷光OLED及如熟習有機電致發光領域技術者所知之所有的磷光錯合物均適宜,且熟習此項技術者將可在無需發明性步驟的情形下使用其他磷光錯合物。
本發明化合物亦適用作有機電致發光裝置中之(特定言之)磷光發射體之基質材料,如(例如)US 2011/0248247及US 2012/0223633中所述。在此等多彩顯示器組件中,額外藍色發射層係藉由在整個區域上進行蒸氣沈積而施加至所有像素(還有彼等具有不同於藍色之顏色的像素)上。出乎意料的是,此處已發現,當用作紅色及/或綠色像素之
基質材料時,本發明化合物仍與經蒸氣沈積的藍色發射層一起產生極佳發射。
在本發明之另一實施例中,本發明有機電致發光裝置不包含單獨的電洞注入層及/或電洞傳遞層及/或電洞阻擋層及/或電子傳遞層,亦即發射層係直接比鄰電洞注入層或陽極及/或發射層係直接比鄰電子傳遞層或電子注入層或陰極,如(例如)WO 2005/053051中所述。此外,可使用與發射層中之金屬錯合物相同或類似的金屬錯合物作為直接比鄰發射層之電洞傳遞或電洞注入材料,如(例如)WO 2009/030981中所述。
在本發明之另一實施例中,本發明化合物係用於電洞傳遞層或電子阻擋層或激子阻擋層中。
在本發明之又另一較佳實施例中,本發明化合物係用作電子傳遞或電子注入層中之電子傳遞材料。此處的發射層可係螢光或磷光的。若該化合物係用作電子傳遞材料,則其較佳經(例如)鹼金屬錯合物(諸如,例如,LiQ(羥基喹啉鋰))摻雜。
在本發明之又另一較佳實施例中,本發明化合物係用於電洞阻擋層中。電洞阻擋層意指在陰極側直接比鄰發射層之層。
在本發明有機電致發光裝置之其他層中,所有材料均可如根據先前技術通常使用的方式使用。因此,熟習此項技術者將可在無需發明性步驟的情形下組合使用所有已知用於有機電致發光裝置之材料與本發明式(1)化合物或上文所指示的較佳實施例。
此外,以特徵在於一或多個層係藉由昇華製程加以塗覆之有機電致發光裝置為較佳,其中該等材料係在真空昇華裝置中藉由蒸氣沈積於低於10-5毫巴(較佳低於10-6毫巴)的初始壓力下施加。然而,初始壓力亦可甚至更低,例如低於10-7毫巴。
亦以特徵在於一或多個層係藉由OVPD(有機蒸氣噴射沈積)製程
或藉由運載氣體昇華加以塗覆之有機電致發光裝置為較佳,其中該等材料係在10-5毫巴與1巴之間之壓力下施加。該製程之特殊情形係OVJP(有機蒸氣噴射印刷)製程,其中該等材料係通過噴嘴直接施加,且因此經結構化(例如M.S.Arnold等人,Appl.Phys.Lett. 2008,92,053301)。
此外,以特徵在於一或多個層係(諸如,例如)藉由旋塗或藉由任何所需印刷製程(諸如,例如,絲網印刷、柔性印刷、平版印刷、LITI(光誘導熱成像法、熱轉移印刷)、噴墨印刷或噴嘴印刷)自溶液製造之有機電致發光裝置為較佳。藉由(例如)適宜取代所獲得的可溶性化合物係達成此目的所必需。
混合製程亦可行,在該等製程中,例如,一或多個層係自溶液施加,且一或多個其他層係藉由蒸氣沈積施加。
該等製程通常係熟習此項技術者所知,且技術者可在無需發明性步驟的情形下將其等應用至包含本發明化合物之有機電致發光裝置。
本發明化合物及本發明有機電致發光裝置之特徵係勝過先前技術之下列出乎意料的優勢中之一或多者:
1.用作螢光或磷光發射體之基質材料之本發明化合物產生較長壽命。特定言之,此適用於該等化合物係用作磷光發射體之基質材料之情形。
2.本發明化合物產生極低操作電壓。特定言之,此適用於該等化合物係用作磷光發射體之基質材料之情形。
此等上述優勢並不會伴隨著其他電子性質之減損。
藉由以下實例來更詳細地說明本發明,但不希望因此而限制本發明。熟習此項技術者將可利用該等說明來在整個所揭示的範圍內實施本發明,並在無需發明性步驟的情形下製備本發明其他化合物,並
將其等用於電子裝置中或應用本發明方法。
除非另有說明,否則以下合成係在保護氣體氣氛下於乾燥溶劑中進行。該等溶劑及試劑可自ALDRICH或ABCR購得。在無法自市場上購得之起始材料之情形下所指示之編號係相應的CAS編號。
將54g(137mmol)4-溴螺-9,9'-二茀(1161009-88-6)、17.9g(140mmol)2-氯苯胺、68.2g(710mmol)第三丁醇鈉、613mg(3mmol)乙酸鈀(II)及3.03g(5mmol)dppf溶解於1.3l甲苯中,並在回流下攪拌5h。使該反應混合物冷卻至室溫,用甲苯加以萃取,並濾過矽藻土。
在真空中蒸發濾液,並使殘餘物自甲苯/庚烷結晶。單離得到呈無色固體之產物。產量:52.2g(118mmol),理論產率86%。
以類似方式製備以下化合物:
將45g(102mmol)(2-氯苯基)-4-螺-9,9'-二茀基胺、56g(409mmol)碳酸鉀、4.5g(12mmol)四氟硼酸三環己基鏻及1.38g(6mmol)乙酸鈀(II)懸浮於500ml二甲基乙醯胺中,並在回流下攪拌6h。冷卻後,用300ml水及600ml二氯甲烷萃取該反應混合物。再攪拌該混合物30min,分離出有機相,濾過短矽藻土床,及然後在真空中移除溶劑。用熱甲苯萃取粗產物,並自甲苯再結晶。單離出呈米黃色固體之產物(32.5g,80mmol,相當於78%之理論產率)。
以類似方式製備以下化合物:
在保護氣氛下,將4.2g含於礦物油之60% NaH(0.106mol)溶解於300ml二甲基甲醯胺中。將43g(0.106mol)螺[9H-茀-9,7'(1'H)-茚并
[1,2-a]咔唑]溶解於250ml DMF中,並滴加至反應混合物中。在室溫下1h後,滴加2-氯-4,6-二苯基-1,3,5-三嗪(34.5g,0.122mol)之200ml THF之溶液。然後在室溫下攪拌該反應混合物12h。此後,將該反應混合物傾倒於冰上。升溫至室溫後,濾出該過程中的沉澱固體,並用乙醇及庚烷加以清洗。用熱甲苯萃取殘餘物,自甲苯/正庚烷再結晶,並最後在高真空中昇華。純度為99.9%。產量為28.4g(44.5mmol;42%)。
以類似方式製備以下化合物:
在回流下,加熱32.8g(81mmol)螺[9H-茀-9,7'(1'H)-茚并[1,2-a]咔唑]、115g(406mmol)1-溴-4-碘苯、22.4g(162mmol)碳酸鉀、1.84g(8.1mmol)1,3-二(2-吡啶基)-1,3-丙二酮、1.55g(8.1mmol)碘化亞銅及1000ml DMF達30h。隨後在旋轉蒸發器中將該反應混合物蒸發至乾。將殘餘物溶解於THF中,並濾過短矽膠床,然後在真空中移除溶劑。隨後使該固體自庚烷/THF中再結晶,並在氧化鋁上用熱庚烷/甲苯加以萃取。濾出冷卻時所沉澱出的固體,並加以乾燥。產量:37g(66mmol),81%。
以類似方式製備以下化合物:
將55ml(138mmol)正丁基鋰(2.5M的己烷溶液)滴加至73g(130mmol)1-溴-9-螺二茀之1500ml THF之冷卻至-78℃的溶液中。在-78℃下攪拌該反應混合物30min。使該混合物達到室溫,再冷卻至-78℃,且然後迅速添加20ml(176mmol)硼酸三甲酯含於50ml THF之混合物。升溫至-10℃後,使用135ml 2N鹽酸水解該混合物。分離出有機相,用水加以清洗,在硫酸鈉上加以乾燥,並蒸發至乾。使殘餘物溶解於300ml正庚烷中,利用抽吸濾出無色固體,用正庚烷加以清洗,並在真空中乾燥。產量:94.5g(255mmol),理論產率99%;純度:根據HPLC為99%。
以類似方式製備以下化合物:
將57.8g(110mmol)螺[9H-茀-9,7'(12'H)-茚并[1,2-a]咔唑]-12'-[4-苯基酸]、29.5g(110.0mmol)2-氯-4,6-二苯基-1,3,5-三嗪及44.6g(210.0mmol)磷酸三鉀懸浮於500ml甲苯、500ml二噁烷及500ml水中。先後將913mg(3.0mmol)三鄰甲苯基膦及112mg(0.5mmol)乙酸鈀(II)添加至該懸浮液中,並在回流下加熱該反應混合物達16h。冷卻後,分離出有機相,濾過矽膠,用200ml水清洗三次,及隨後蒸發至乾。使殘餘物自甲苯/庚烷再結晶,及最後在高真空中昇華(p=5 x 10-5毫巴,T=377℃)。產量為29.2g(41mmol),相當於37%之理論產率。
以類似方式製備以下化合物:
將43g(106mmol)螺[9H-茀-9,7'(1'H)-茚并[1,2-a]咔唑]、17.9g(114mmol)溴苯及30.5g NaOtBu懸浮於1.5l對二甲苯中。將含於甲苯之0.5g(2.11mmol)Pd(OAc)2及4.2ml 1M三第三丁基膦溶液添加至該懸浮液中。在回流下加熱該反應混合物達16h。冷卻後,分離出有機相,用水清洗三次,每次200ml,及隨後蒸發至乾。用熱甲苯萃取殘餘物,自甲苯再結晶,及最後在高真空中昇華。純度為99.9%,產量為21.4g(44.5mmol;42%)。
以類似方式製備以下化合物:
在500ml四頸燒瓶中,將7g(14.5mmol)苯基-4-螺咔唑及2.7g(15mmol)NBS溶解於300ml THF中,並在室溫下攪拌48h,直至反應完成。隨後用50ml水水解該混合物,並在減壓下移除有機溶劑。
藉由用300ml熱乙醇攪拌一次清洗所得固體。冷卻至室溫後,濾出固體。在減壓下乾燥後,獲得呈無色固體之產物。產量為7.3g(13mmol,相當於90%理論產率)。
在1l四頸燒瓶中,將17.5g(31mmol)8a、9.2g(32mmol)苯基咔唑酸、26.5g(125mmol)磷酸三鉀溶解於120ml乙二醇二甲醚、170ml甲苯及120ml水中,並使氬氣穿過該混合物,歷時30min。隨後添加140mg(0.6mmol)乙酸鈀及380mg(1.2mmol)三鄰甲苯基膦,並在回流下加熱該混合物達16h。當反應完成時,使該反應混合物冷卻至室溫,濾出沉澱固體,並用乙醇及庚烷加以清洗。隨後用熱甲苯萃取該固體兩次,自庚烷/甲苯再結晶,並在400℃及2 x 10-5巴下昇華。獲得呈無色固體之產物,其具有99.95%之HPLC純度。產量為10.2g(14mmol,相當於45%之理論產率)。
以類似方式製備以下化合物:
在2l四頸燒瓶中,在回流下加熱含於1000ml無水二噁烷之33.8g(71mmol)聯苯-2-基聯苯-4-基-(4-溴苯基)胺(1371651-92-1)、21.9g(86mmol)雙頻哪醇根基二硼烷(73183-34-3)、21.7g(221mmol)乙酸鉀及1.7g(2.1mmol)1,1-雙(二苯基膦基)二茂鐵二氯化鈀(II)錯合物及
DCM加熱達16h,直至反應完成。冷卻至室溫後,用乙酸乙酯萃取有機相,用300ml水清洗三次,並用硫酸鈉加以乾燥。在旋轉蒸發器中將合併的有機相蒸發至乾。自庚烷再結晶後,獲得呈固體之產物。產量為22.6g(41mmol;61%)。
以類似方式製備以下化合物:
在用70℃油浴進行二次加熱下,自2.7g(110mmol)經碘活化的鎂切屑及25.6g(110mmol)2-溴聯苯、0.8ml 1,2-二氯乙烷、50ml 1,2-二甲氧基乙烷、400ml THF及200ml甲苯之混合物製備相應格利雅(Grignard)試劑。當鎂完全反應時,使該混合物冷卻至室溫,及然後滴加25.9g(100mmol)4-[聯苯-4-基-(9,9-二甲基-9H-茀-2-基)胺基]茀-9-酮(7h)之500ml THF之溶液,在50℃下加熱該反應混合物達4h,且然後在室溫下又攪拌12h。添加100ml水,簡單攪拌混合物,分離出有機相,並在真空中移除溶劑。在40℃下,使殘餘物懸浮於500ml溫暖的冰乙酸中,將0.5ml濃硫酸添加至該懸浮液中,且隨後在100℃下再攪拌混合物2h。冷卻後,利用抽吸濾出沉澱固體,用100ml冰乙酸清洗一次,用乙醇清洗三次,每次100ml,及最後自二噁烷
再結晶。產量:26.9g(68mmol),68%;根據1H-NMR之純度為約98%。
以類似方式製備以下化合物:
首先將24.0g(142mmol,1.2當量)4-胺基聯苯(CAS 92-67-1)及32.0g(117mmol,1.0當量)2-溴-9,9'-二甲基茀(CAS 28320-31-2)引入950ml甲苯中,並充滿氬30分鐘。隨後添加1.0g(1.8mmol,0.02當量)1,1'-雙(二苯基膦基)二茂鐵(CAS 12150-46-8)、350mg(1.6mmol,0.01當量)乙酸鈀(II)(CAS 3375-31-3)及29g(300mmol,2.6當量)第三丁醇鈉(CAS 865-48-5),並在回流下隔夜加熱混合物。當反應
完成時,用300ml甲苯稀釋該批料,並用水加以萃取。在硫酸鈉上乾燥有機相,並在旋轉蒸發器中移除溶劑。將50ml乙酸乙酯添加至棕色油中,並將該混合物添加至庚烷/乙酸乙酯的20:1混合物中。利用抽吸濾出所形成的固體,並用庚烷加以清洗。乾燥得到29g(80mmol,69%)所需產物,其具有99.1%之HPLC純度。
以類似方式製備以下化合物:
將29g(80mmol,1.0當量)中間體12a及25g(80mmol,1.0當量)3,3'-二溴-1,1'-聯苯(CAS 16400-51-4)溶解於600ml甲苯中,並脫氣30分鐘。隨後添加45g(240mmol,3.0當量)第三丁醇鈉、890mg(0.40mmol,0.050當量)乙酸鈀(II)及8ml(8.0mmol,0.10當量)1M三第三丁基膦溶液。在回流下隔夜加熱該批料,並在反應完成時,連同甲苯濾過氧化鋁兩次。在旋轉蒸發器中移除溶劑後,使油溶解於少量THF中,並引入庚烷中。利用抽吸濾出所形成的固體,並藉由庚烷/甲苯1:1進行熱萃取加以純化,得到16.6g(28mmol,35%)所需產物。
首先將7.9g(330mmol,1.2當量)鎂切屑引入1l四頸燒瓶中,並足夠緩慢地添加63g(270mmol,1.0當量)3-溴聯苯(CAS 2113-57-7)的THF溶液,以獲得反應混合物之回流。當完成添加時,在回流下再加熱該批料達2h。
在2l四頸燒瓶中,將含於500ml THF之50g(270mmol,1當量)2,4,6-三氯-1,3,5-三嗪(CAS 108-77-0)冷卻至-10℃。在該溫度下足夠緩慢地滴加格利雅溶液,使該溫度不超過0℃,及最後在室溫下隔夜攪拌該批料。就處理而言,滴加270ml 1N鹽酸,並攪拌該混合物1h。隨後分離出水相,並用乙醚加以萃取。在硫酸鈉上乾燥合併的有機相,並在旋轉蒸發器中移除溶劑,得到56g(69%)無色油。
以類似方式製備以下化合物:
步驟2:
變體A:將18g(50mmol,1當量)9,9-螺二茀-2-基酸(CAS 236389-21-2)、15g(50mmol,1當量)2-聯苯-3-基-4,6-二氯-1,3,5-三嗪14a及5.8g(55mmol,1.1當量)碳酸鈉溶解於200ml二噁烷、200ml甲苯及70ml水之混合物中,並脫氣30分鐘。隨後添加580mg(0.50mmol,1莫耳%)肆(三苯基膦)(CAS 14221-01-3),並在回流下隔夜加熱該批料。使反應混合物冷卻,並添加300ml水。用乙酸乙酯萃取水相三次,合併有機相,並在旋轉蒸發器中移除溶劑。用庚烷/甲苯4:1進行熱萃取得到15g(26mmol,51%)無色固體。
變體B:類似於步驟1。
以類似方式製備以下化合物:
下文實例V1至E77中呈現各種OLED之數據(參見表1及2)。
實例V1-V7及E1-E49之預處理:為改良加工,用20nm PEDOT:PSS(聚(3,4-伸乙基二氧噻吩)聚(苯乙烯磺酸鹽),其係作為CLEVIOSTM P VP AI 4083自Heraeus Precious Metals GmbH,Germany購得,其係自水溶液藉由旋塗施加)塗覆已經50nm厚度的結構化ITO(氧化銦錫)塗覆的清潔玻璃板(在Miele實驗室洗碟機中清潔,Merck Extran洗滌劑)。隨後藉由在180℃下加熱10min乾燥該等樣品。該等經塗覆的玻璃板形成施加OLED之基板。
實例E50-E55之預處理:用氧電漿處理已經50nm厚度的結構化ITO(氧化銦錫)塗覆之清潔玻璃板(在Miele實驗室洗碟機中清洗,Merck Extran洗滌劑)達130s。此等經電漿處理的玻璃板形成施加OLED之基板。在塗覆前,將該等基板保持在真空下。在電漿處理後的10min內開始塗覆。
實例E56-E77之預處理:用氧電漿處理已經50nm厚度的結構化ITO(氧化銦錫)塗覆之清潔玻璃板(在Miele實驗室洗碟機中清洗,Merck Extran洗滌劑)達130s,隨後用氬電漿處理達150s。此等經電漿處理的玻璃板形成施加OLED之基板。在塗覆前,將該等基板保持在真空下。在電漿處理後的10min內開始塗覆。
該等OLED基本上具有以下層結構:基板/可選的電洞注入層(HIL)/電洞傳遞層(HTL)/中間層(IL)/電子阻擋層(EBL)/發射層(EML)/可選的電洞阻擋層(HBL)/電子傳遞層(ETL)/可選的電子注入層(EIL)及
最後的陰極。該陰極係由鋁層形成,厚度為100nm。該等OLED之精確結構顯示於表1中。製造該等OLED所需的材料顯示於表3中。此處諸如「3a」之標示與表中所顯示的實例3a的材料有關。類似情形適用於其他材料。
化合物WB1之合成係類似於WO 2009/124627進行。化合物TEG3之合成係描述於WO 2011/032626中,化合物TER2之合成係描述於WO 2011/032626中,化合物IC4之合成係描述於WO 2010/136109中。
所有的材料均係在真空腔室中藉由熱蒸氣沈積施加。此處的發射層始終由至少一種基質材料(主體材料)及發射摻雜劑(發射體)組成,該發射摻雜劑係藉由共蒸發與該基質材料或該等基質材料呈一定體積比例地摻合在一起。此處諸如ST1:7b:TEG1(30%:58%:12%)之表述意指材料ST1係以30體積%之比例存在於該層中,7b係以58%之比例存在於該層中,且TEG1係以12%之比例存在於該層中。類似地,該電子傳遞層亦可由兩種材料之混合物組成。
該等OLED係藉由標準方法表徵。為此,測定作為發光密度(自假定Lambert發射特性之電流/電壓/發光密度特徵線(IUL特徵線)計算)之函數之電致發光光譜、電流效率(以cd/A計)、功率效率(以lm/W計)及外部量子效率(EQE,以百分數計),及壽命。在1000cd/m2之發光密度下測定電致發光光譜,並由此計算CIE 1931 x及y顏色座標。表2中之術語U1000表示得到1000cd/m2之發光密度所需的電壓。CE1000及PE1000分別表示在1000cd/m2下所達到之電流效率及功率效率。最後,EQE1000表示在1000cd/m2之操作發光密度下之外部量子效率。
壽命LT係定義為發光密度在恒定電流密度下操作時自初始發光密度下降至某一比例L1所經歷之時間。表X2中之表述L0;j0=4000cd/m2及L1=70%意指LT欄中所示壽命對應於發光密度自其初始值4000cd/m2下降至2800cd/m2所經歷之時間。類似地,L0;j0=20mA/cm2,
L1=80%意指發光密度在20mA/cm2下操作時間LT後下降至其初始值之80%。
該等各種OLED之數據係匯總於表2中。實例V1-V7係根據先前技術之比較實例,實例E1-E77顯示包含本發明材料之OLED之數據。
下文中更詳細闡述一些該等實例以說明本發明化合物之優勢。
然而,應指出的是,此僅代表表2中所示數據之精選。從表中可看出,在一些情形下,使用並未作更詳細描述的本發明化合物時,所有參數亦可達成勝過先前技術之顯著提升,但在一些情形下,僅觀察到效率或電壓或壽命之提升。然而,即使該等參數中之一者之提升亦代表著重大進展,因為不同應用需要最優化不同參數。
本發明化合物作為電子傳遞材料之用途
若使用本發明類似螺化合物3a代替根據先前技術之二苯基茀化合物StdT2作為電子傳遞材料,則與綠色磷光摻雜劑TEG1組合會使功率效率獲得約15%的顯著提升,此為電壓之顯著提升及外部量子效率之提升之故。壽命同樣略有提升(實例V6、E24)。與藍色螢光摻雜劑D1組合亦獲得極佳性能數據(實例E25)。
本發明化合物在磷光OLED中作為基質材料之用途
與綠色磷光摻雜劑TEG1組合時,與化合物StdT1(其中三嗪基團係鍵合至螺之茀部分)相比,使用本發明化合物3a(其中三嗪係經由氮鍵合)獲得電壓顯著提升0.3V,且壽命顯著提升35%。外部量子效率亦提升,此總體上導致功率效率顯著提升幾乎20%(實例V1、E1)。與二苯基茀化合物StdT2相比,特別觀察到壽命提升(實例V4、E1)。使用本發明化合物時,與紅色磷光摻雜劑TER1組合會出現類似改良(實例V5、E30、E31)。
在發射層中與化合物IC3組合時,本發明化合物亦可獲得顯著優勢(實例V7、E21),尤其是壽命提升幾乎40%。
最終,本發明化合物與化合物ST1或IC2在發射層中之組合得到極佳性能數據(實例E39、E40、E41、E42)。
諸多本發明材料亦可自溶液加工,且與進行真空加工的OLED相比,此得到明顯更容易製造的OLED,但仍然具有良好性質。特定言之,本發明基質材料對具有經溶液加工的發射層之組件之操作壽命及效率具有積極影響。基於全溶液之OLED之製造已多次描述在文獻資料(例如WO 2004/037887)中。
在下文所論述的實例中,將基於溶液及基於真空施加之層組合於OLED中,因此自溶液進行加工直至發射層且包括發射層,且後續
層係藉由在真空中熱蒸發進行。出於此目的,上述一般製程適用於此處所述情形(層厚度變化,材料),且係如下組合。
為改良加工,用20nm(就綠色發射OLED而言)或80nm(就紅色發射OLED而言)PEDOT:PSS((聚(3,4-伸乙基二氧噻吩)聚(苯乙烯磺酸鹽),其係作為CLEVIOSTM P VP AI 4083自Heraeus Precious Metals GmbH,Germany購得,其係自水溶液藉由旋塗施加)塗覆已經50nm厚度的結構化ITO(氧化銦錫)塗覆之清潔玻璃板(在Miele實驗室洗碟機中清潔,Merck Extran洗滌劑)。隨後藉由在180℃下加熱10min乾燥此等基板。
將厚度為20nm之電洞傳遞層施加至此等基板。其係由具有以下結構式之聚合物組成,
其已根據WO 2010/097155合成。將該材料溶解於甲苯中。該溶液之固體含量為5g/l。在氮氣氛中,藉由旋塗自該溶液施加厚為20nm之層。隨後在氮氣氛中藉由在180℃下加熱60min乾燥該樣品。
然後施加發射層。該發射層始終由至少一種基質材料(主體材料)及發射摻雜劑(發射體)組成。此外,可出現複數種基質材料及共摻雜劑之混合物。諸如基質(92%):摻雜劑(8%)之表述意指:基質材料係以92%之重量比且摻雜劑係以8%之重量比存在於製造發射層之溶液中。將用於該發射層之相應固體混合物溶解於甲苯中。固體含量為18g/l。在氮氣氛中藉由旋塗施加該發射層,並在氮氣氛中藉由在180℃下加熱10分鐘進行乾燥。
隨後將該等樣品引入真空腔室中,不與空氣接觸,並藉由蒸發施加兩個其他層。若一個此種層係由複數種材料組成,則上述命名法適用於個別組分之混合比。
該等OLED係如上文所述進行表徵。為測量壽命,在經設定以獲得某一初始發光密度之恆定電流下操作該等OLED。壽命LT80@8000係定義為發光密度自其初始值8000cd/m2下降至80%(亦即下降至6400cd/m2)所需的時間。其他初始亮度或其他最終發光密度百分比下之壽命值係相應地加以定義。
比較實例LV1:根據先前技術,將固體混合物IC4(40%):WB1(40%):TEG3(20%)用於發射層。如上所述,自其製造厚度為60nm之發射層。隨後在真空中藉由熱蒸發先後施加厚度為10nm之ST2材料層及厚度為40nm之ST2:LiQ(50%:50%)層。隨後在真空中藉由蒸發施加厚度為100nm之鋁層作為陰極。該OLED發射綠光,且獲得U1000=4.6V,EQE1000=17.8%,LT80@10000=115h,LT90@10000=28h。
本發明實例LE1:該OLED對應實例LV1,不同之處在於使用混合物3q(40%):WB1(40%):TEG3(20%)代替混合物IC4(40%):WB1(40%):TEG3(20%)。該OLED發射綠光,且獲得U1000=4.6V,EQE1000=18.3%,LT80@10000=120h,LT90@10000=37h。
本發明實例LE2:該OLED對應實例LV1,不同之處在於使用混合物3p(40%):WB1(40%):TEG3(20%)代替混合物IC4(40%):WB1(40%):TEG3(20%)。該OLED發射綠光,且獲得U1000=4.5V,EQE1000=18.4%,LT80@10000=130h,LT90@10000=38h。
本發明實例LE3:該OLED對應實例LV1,不同之處在於使用混
合物3a(40%):WB1(40%):TEG3(20%)代替混合物IC4(40%):WB1(40%):TEG3(20%)。該OLED發射綠光,且獲得U1000=4.4V,EQE1000=18.8%,LT80@10000=240h,LT90@10000=75h。
比較實例LV2:該OLED對應實例LV1,不同之處在於使用混合物IC5(40%):WB1(30%):TEG3(30%)代替混合物IC4(40%):WB1(40%):TEG3(20%)。該OLED發射綠光,且獲得U1000=4.0V,EQE1000=19.7%,LT80@10000=335h,LT90@10000=87h。
本發明實例LE4:該OLED對應實例LV2,不同之處在於使用混合物3a(40%):WB1(30%):TEG3(30%)代替混合物IC5(40%):WB1(30%):TEG3(30%)。該OLED發射綠光,且獲得U1000=4.0V,EQE1000=21.4%,LT80@10000=520h,LT90@10000=195h。
比較實例LV3:該OLED對應實例LV1,不同之處在於使用混合物IC5(40%):WB1(24%):TEG3(30%):TER2(6%)代替混合物IC4(40%):WB1(40%):TEG3(20%)。該OLED發射紅光,且獲得U1000=6.0V,EQE1000=13.5%,LT80@8000=180h,LT90@8000=48h。
本發明實例LE5:該OLED對應實例LV3,不同之處在於使用混合物3a(40%):WB1(24%):TEG3(30%):TER2(6%)代替混合物IC5(40%):WB1(24%):TEG3(30%):TER2(6%)。該OLED發射紅光,且獲得U1000=5.6V,EQE1000=13.8%,LT80@8000=255h,LT90@8000=82h。
本發明實例LE6:該OLED對應實例LV3,不同之處在於使用混合物3p(40%):WB1(24%):TEG3(30%):TER2(6%)代替混合物
IC5(40%):WB1(24%):TEG3(30%):TER2(6%)。該OLED發射紅光,且獲得U1000=6.0V,EQE1000=13.8%,LT80@8000=275h,LT90@8000=81h。
本發明實例LE7:該OLED對應實例LV3,不同之處在於使用混合物3q(40%):WB1(24%):TEG3(30%):TER2(6%)代替混合物IC5(40%):WB1(24%):TEG3(30%):TER2(6%)。該OLED發射紅光,且獲得U1000=6.0V,EQE1000=14.0%,LT80@8000=250h,LT90@8000=68h。
比較實例LV4:根據先前技術,將固體混合物IC4(40%):WB1(40%):TEG3(20%)用於發射層。如上所述,自其製造厚度為60nm之發射層。隨後在真空中藉由熱蒸發先後施加厚度為20nm之M1:D1(95%:5%)層及厚度為20nm之ST2:LiQ(50%:50%)層。隨後在真空中藉由蒸發施加厚度為100nm之鋁層作為陰極。該OLED發射綠光,且獲得U1000=5.0V,EQE1000=16.7%,LT80@10000=33h,LT90@10000=8h。
比較實例LV5:該OLED對應實例LV4,不同之處在於使用混合物IC5(40%):WB1(40%):TEG3(20%)代替混合物IC4(40%):WB1(40%):TEG3(20%)。該OLED發射綠光,且獲得U1000=4.3V,EQE1000=15.0%,LT80@10000=29h,LT90@10000=8h。
本發明實例LE8:該OLED對應實例LV4,不同之處在於使用混合物3a(40%):WB1(40%):TEG3(20%)代替混合物IC4(40%):WB1(40%):TEG3(20%)。該OLED發射綠光,且獲得U1000=4.3V,EQE1000=16.9%,LT80@10000=88h,LT90@10000=25h。
藉由比較實例LV1與LE1-LE3,LV2與LE4,LV3與LE5-LE7及
LV4以及LV5與LE8可看出,用包含本發明化合物之混合物所得到之所有參數均改良,特別係LT90之極顯著增加,其對顯示器應用很重要。
Claims (15)
- 一種式(1)或式(1A)化合物,
- 如請求項1之化合物,其中X在每次出現時相同或不同地表示CR1或N,其中每環中最多一個基團X表示N;或兩個相鄰基團X表示式(2)或(3)基團,其中Z在每次出現時相同或不同地表示CR1,且V在每次出現時相同或不同地表示NR1、C(R1)2、O或S。
- 如請求項1或2之化合物,其係選自式(5)至(12)化合物,
- 如請求項1至3中任一項之化合物,其係選自式(5a)至(12a)結構,
- 如請求項1至4中任一項之化合物,其中R在每次出現時相同或不同地選自由下列組成之群:H、F、CN、N(Ar1)2、具有1至10個C原子之直鏈烷基或具有3至10個C原子之分支鏈或環狀烷基或具有6至30個芳族環原子之芳族環系統(其可經一或多個非芳族基團R2取代),且其中R1在每次出現時相同或不同地選自由下列組成之群:H、D、F、Br、CN、N(Ar1)2、C(=O)Ar1、P(=O)(Ar1)2、具有1至10個C原子之直鏈烷基或烷氧基或具有3至10個C原子之分支鏈或環狀烷基或烷氧基或具有2至10個C原子之烯基或炔基(其中各者可經一或多個基團R2取代,其中一或多個非相鄰CH2基團可經O置換,且其中一或多個H原子可經D或F置換)、具有5至30個芳族環原子之芳族或雜芳族環系統(其在每次出現時可經一或多個基團R2取代)。
- 如請求項1至5中任一項之化合物,其中Ar係選自具有5至24個芳族環原子之芳族或雜芳族環系統(其在每次出現時可經一或多個基團R1取代),較佳係苯、鄰-、間-或對-聯苯、鄰-、間-、對-或分支鏈聯三苯、鄰-、間-、對-或分支鏈四聯苯、1-、2-或3-茀基、1-、2-、3-或4-螺二茀基、1-或2-萘基、吡咯、呋喃、噻吩、吲哚、苯并呋喃、苯并噻吩、1-、2-或3-咔唑、1-、2-或3-二苯并呋喃、1-、2-或3-二苯并噻吩、茚并咔唑、吲哚并咔唑、2-、3-或4-吡啶、2-、4-或5-嘧啶、吡嗪、噠嗪、三嗪、蒽、菲、三亞苯、芘、苯并蒽或此等基團中之二者或三者之組合,其中各者可經一或多個基團R1取代。
- 如請求項1至6中任一項之化合物,其中在下式(Het-Ar)基團中,
- 如請求項7之化合物,其中該基團(Het-Ar)係選自式(Het-Ar-1)至(Het-Ar-10)基團,
- 如請求項1至8中任一項之化合物,其中其不含其中多於兩個六員環係彼此直接縮合在一起的縮合芳基或雜芳基。
- 一種製備如請求項1至9中任一項之化合物之方法,其包括以下反應步驟:a)合成尚未含基團(Het-Ar)及/或Ar之化合物(1)或(1A)之骨架;及b)使該來自a)之骨架在C-C偶合(諸如鈴木偶合、根岸偶合、山本偶合、格利雅交叉偶合或斯蒂爾偶合等)或C-N偶合(諸如布赫瓦爾德偶合或烏爾曼偶合)中反應。
- 一種包含一或多種如請求項1至9中任一項之化合物之寡聚物、聚合物或樹枝狀聚合物,其中該化合物至該聚合物、寡聚物或樹枝狀聚合物之一或多個鍵結係存在於一或多個位置而非取代基上。
- 一種調配物,其包含至少一種如請求項1至9中任一項之化合物或如請求項11之寡聚物、聚合物或樹枝狀聚合物及至少一種溶劑。
- 一種如請求項1至9中任一項之化合物或如請求項11之寡聚物、聚合物或樹枝狀聚合物於電子裝置中之用途。
- 一種電子裝置,其包括至少一種如請求項1至9中任一項之化合物或如請求項11之寡聚物、聚合物或樹枝狀聚合物,特定言之,其係選自由下列組成之群:有機電致發光裝置、有機積體電路、有機場效電晶體、有機薄膜電晶體、有機發光電晶體、有機太陽能電池、染料敏化有機太陽能電池、有機光學偵測器、有機光感受器、有機場淬滅裝置、發光電化學電池、有機雷射二極體及「有機電漿子發射裝置」。
- 如請求項14之電子裝置,其係有機電致發光裝置,其中如請求項1至9中任一項之化合物係用作磷光或螢光發射體之基質材料及/或用於電子阻擋或激子阻擋層中及/或用於電洞傳遞層中及/或用於電洞阻擋層中及/或用於電洞阻擋或電子傳遞層中。
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CN107075363A (zh) * | 2014-11-11 | 2017-08-18 | 罗门哈斯电子材料韩国有限公司 | 多种主体材料和包含其的有机电致发光装置 |
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KR20150100825A (ko) | 2015-09-02 |
KR102195986B1 (ko) | 2020-12-29 |
JP6342419B2 (ja) | 2018-06-13 |
KR102321547B1 (ko) | 2021-11-03 |
JP2016506399A (ja) | 2016-03-03 |
KR20200143531A (ko) | 2020-12-23 |
US10227528B2 (en) | 2019-03-12 |
EP2935276A1 (de) | 2015-10-28 |
EP2935276B1 (de) | 2017-11-01 |
WO2014094963A1 (de) | 2014-06-26 |
CN104903328A (zh) | 2015-09-09 |
CN104903328B (zh) | 2018-03-30 |
TWI601804B (zh) | 2017-10-11 |
US20150337197A1 (en) | 2015-11-26 |
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