TW201619152A - 有機電激發光裝置之材料 - Google Patents
有機電激發光裝置之材料 Download PDFInfo
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- TW201619152A TW201619152A TW104124263A TW104124263A TW201619152A TW 201619152 A TW201619152 A TW 201619152A TW 104124263 A TW104124263 A TW 104124263A TW 104124263 A TW104124263 A TW 104124263A TW 201619152 A TW201619152 A TW 201619152A
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- 239000000463 material Substances 0.000 title description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 88
- 239000011159 matrix material Substances 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 15
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims abstract description 14
- 230000008569 process Effects 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims description 133
- 125000004432 carbon atom Chemical group C* 0.000 claims description 57
- -1 NR 5 Inorganic materials 0.000 claims description 47
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 25
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000004305 biphenyl Substances 0.000 claims description 16
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 235000010290 biphenyl Nutrition 0.000 claims description 12
- 230000000903 blocking effect Effects 0.000 claims description 11
- 229910052805 deuterium Inorganic materials 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 6
- 238000005859 coupling reaction Methods 0.000 claims description 6
- 230000005525 hole transport Effects 0.000 claims description 6
- 238000006467 substitution reaction Methods 0.000 claims description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
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- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 3
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- 230000031709 bromination Effects 0.000 claims description 3
- 238000005893 bromination reaction Methods 0.000 claims description 3
- 230000026030 halogenation Effects 0.000 claims description 3
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
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- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004437 phosphorous atom Chemical group 0.000 claims description 2
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- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 1
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical class C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 abstract description 2
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- 125000002950 monocyclic group Chemical group 0.000 description 6
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- 125000004122 cyclic group Chemical group 0.000 description 4
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- 239000002019 doping agent Substances 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
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- 229910010272 inorganic material Inorganic materials 0.000 description 3
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- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
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- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
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- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
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- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- VXNSQGRKHCZUSU-UHFFFAOYSA-N octylbenzene Chemical compound [CH2]CCCCCCCC1=CC=CC=C1 VXNSQGRKHCZUSU-UHFFFAOYSA-N 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
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- 125000004430 oxygen atom Chemical group O* 0.000 description 1
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- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
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- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
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- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
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Abstract
本發明描述二苯並呋喃和二苯並噻吩衍生物,特別是用作有機電激發光裝置中之三重態基質材料。本發明此外關於一種用於製備根據本發明化合物之方法及包含此等化合物之電子裝置。
Description
本發明描述二苯並呋喃或二苯並噻吩衍生物,特別是用作有機電激發光裝置中之三重態基質材料。本發明此外關於一種用於製備根據本發明化合物之方法及包含此等化合物之電子裝置。
其中使用有機半導體作為功能材料之有機電激發光裝置(OLED)的結構係描述於(例如)US 4539507、US 5151629、EP 0676461及WO 98/27136中。所使用的發光材料經常為呈現磷光而非螢光之有機金屬錯合物。為了量子力學的原因,使用有機金屬化合物作為磷光發光體,能量及功率效率可能增加高達四倍。通常,在OLED的情況下,特別是亦在呈現三重態發光(磷光)之OLED的情況下,皆仍需要改良,例如關於效率、操作電壓及壽命。磷光OLED之性質不只由所使用之三重態發光體決定。特別是,所使用的其他材料,諸如(例如)基質材料,在此也特別重要。此等材料的改良因此也可導致OLED性質的顯著
改良。
根據先前技術,尤其是咔唑衍生物(例如根據WO 2014/015931)、吲哚並咔唑衍生物(例如根據WO 2007/063754或WO 2008/056746)或茚並咔唑衍生物(例如根據WO 2010/136109或WO 2011/000455),特別是彼等經缺電子雜芳族化合物(諸如三)取代者,係用作為磷光發光體之基質材料。此外,雙二苯並呋喃衍生物(例如根據EP 2301926)例如係用作磷光發光體之基質材料。WO 2013/077352揭示三衍生物,其中三基經由二價伸芳基鍵結至二苯並呋喃基。此等化合物係描述為電洞阻擋材料。未揭示此等材料作為磷光發光體之主體的用途。
通常,在用作基質材料之材料的情況中仍然需要改良,特別是關於該裝置的壽命,且也關於裝置的效率和操作電壓。
本發明之目的為提供適合使用於磷光或螢光OLED(特別是作為基質材料)的化合物。特別地,本發明之目的為提供適合於紅色-、黃色-和綠色-磷光OLED及隨意地亦適合於藍色-磷光OLED且其導致長壽命、良好效率和低操作電壓的基質材料。
令人驚訝地,已經發現:包含下式(1)之化合物的電激發光裝置具有超越先前技術之改良,特別是用作磷光摻雜劑之基質材料時。
本發明因此關於下式(1)之化合物,
其中下列適用於所使用的符號:A 在每次出現時相同或不同地為CR1或N,其中每個環最多二個A基團代表N;Y1 為O或S;L 為單鍵或具有5至30個芳族環原子之芳族或雜芳族環系統,其可經一或多個R1基團取代;HetAr 為式(2)、(3)或(4)之基團,
其中虛線鍵表示此基團的鍵聯;X 在每次出現時相同或不同地為CR2或N,其先決條件為至少一個符號X代表N;N1 為式(5)或(6)之基團,
其中虛線鍵表示此基團的鍵聯,及式(6)中之A具有上述所給定之意義;
Ar1 在每次出現時相同或不同地為具有5至30個芳族環原子之芳族或雜芳族環系統,其可經一或多個R3基團取代;W 在每次出現時相同或不同地為CR1或N,其中最多二個W基團代表N,或恰巧二個相鄰的W基團一起代表式(7)或(8)之基團,及其餘W基團在每次出現時相同或不同地代表CR1或N,
其中虛線鍵表示此基團的鍵聯,及A具有上述所給定之意義;Y2、Y3在每次出現時相同或不同地為O、NR4、S、C(R4)2、Si(R4)2、BR4或C=O,其中鍵結至N之R4基團不等於H;R1、R2、R3、R4 在每次出現時相同或不同地選自由下列所組成之群組:H、D、F、Cl、Br、I、CN、NO2、N(Ar2)2、N(R5)2、C(=O)Ar2、C(=O)R5、P(=O)(Ar2)2、P(Ar2)2、B(Ar2)2、Si(Ar2)3、Si(R5)3、具有1至20個C原子之直鏈烷基、烷氧基或硫烷基或具有3至20個C原子之支鏈或環狀烷基、烷氧基或硫烷基或具有2至20個C原子之烯基(彼等各自可經一或
多個R5基團取代,其中一或多個非相鄰CH2基團可經R5C=CR5、Si(R5)2、C=O、C=NR5、P(=O)(R5)、SO、SO2、NR5、O、S或CONR5置換及其中一或多個H原子可經D、F、Cl、Br、I、CN或NO2置換)、具有5至40個芳族環原子之芳族或雜芳族環系統(其在各情況下可經一或多個R5基團取代)、具有5至40個芳族環原子之芳氧基或雜芳氧基(其可經一或多個R5基團取代)、或具有5至40個芳族環原子之芳烷基或雜芳烷基(其可經一或多個R5基團取代);二個相鄰的R1取代基或二個相鄰的R3取代基在此可隨意地形成脂族環系統(其可經一或多個R5基團取代),及二個相鄰的R4取代基可形成脂族或芳族環系統(其可經一或多個R5基團取代);Ar2 在每次出現時相同或不同地為具有5至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R5取代);鍵結至相同的N原子、P原子或B原子之二個Ar2基團在此也可以單鍵或選自N(R5)、C(R5)2、O或S之橋彼此橋聯;R5 在每次出現時相同或不同地選自由下列所組成之群組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(其中一個或多個H原子可經D、F、Cl、Br、I或CN置換且其可經一或多個各自具有1至4個碳原子之烷基取代);二或多個相鄰的R5取代基在此可彼此形成脂族環系統。
相鄰的取代基就本發明之意義而言為鍵結至彼此直接連接的碳原子或鍵結至相同碳原子上的取代基。
就本申請案之目的而言,二或多個基團彼此可形成環之規劃特別意指:二個基團彼此以一化學鍵連接。此以下列流程進行說明:
然而,此外,上述規劃也意指:在二基團之一表示氫的情況下,第二基團鍵結於氫原子所鍵結之位置,且形成一環。
縮合芳基就本發明之意義而言為其中二或多個芳族基縮合之基團,即彼此經由共用邊環化,諸如(例如)萘。相比之下,例如,茀就本發明之意義而言不為縮合芳基,因為茀中之二個芳族基沒有共用邊。
芳族環系統就本發明之意義而言在環系統中含有6至40個C原子。芳族環系統就本發明之意義而言意指不一定只含有芳基或雜芳基,而是此外其中多個芳基或雜芳基可以非芳族單元(較佳為少於10%非H之原子)(諸如,例
如C、N或O原子)連接的系統。因此,例如,系統諸如茀、9,9’-螺聯茀、9,9-二芳基茀、三芳基胺、等等就本發明之意義而言亦意欲為芳族環系統,如為其中二或多個芳基例如以短烷基連接之系統。此外,經由單鍵彼此連結之芳族環(即寡聚伸芳基或寡聚伸雜芳基,諸如(例如)聯苯基、聯三苯基或聯四苯基)就本發明之意義而言係指芳族環系統。
就本發明之目的而言,含有1至40個C原子且其中,此外,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、五氟乙氧基或2,2,2-三氟乙氧基。具有1至40個C原子之硫烷基(thioalkyl)特別是意指甲硫基、乙硫基、正丙硫基、異
丙硫基、正丁硫基、異丁硫基、第二丁硫基、第三丁硫基、正戊硫基、第二戊硫基、正己硫基、環己硫基、正庚硫基、環庚硫基、正辛硫基、環辛硫基、2-乙基己硫基、三氟甲硫基、五氟乙硫基、2,2,2-三氟乙硫基、乙烯硫基、丙烯硫基、丁烯硫基、戊烯硫基、環戊烯硫基、己烯硫基、環己烯硫基、庚烯硫基、環庚烯硫基、辛烯硫基、環辛烯硫基、乙炔硫基、丙炔硫基、丁炔硫基、戊炔硫基、己炔硫基、庚炔硫基或辛炔硫基。通常,根據本發明之烷基、烷氧基或硫烷基可為直鏈、支鏈或環狀,其中一或多個非相鄰的CH2基團可經上述基團置換;再者,一或多個H原子也可經D、F、Cl、Br、I、CN或NO2置換,較佳地經F、Cl或CN置換,進一步較佳地經F或CN置換,特佳地經CN置換。
具有5-40個芳族環原子之芳族或雜芳族環系統意指(特別是)衍生自下列之基團:苯、萘、蒽、苯並蒽、菲、芘、(chrysene)、苝、1,2-苯並苊(fluoranthene)、稠四苯、稠五苯、苯並芘、聯苯、伸聯苯(biphenylene)、聯三苯(terphenyl)、伸聯三苯(triphenylene)、茀、螺聯茀、二氫菲、二氫芘、四氫芘、順-或反-茚並茀、順-或反-茚並咔唑、順-或反-吲哚並咔唑、三聚茚(truxene)、異三聚茚(isotruxene)、螺三聚茚、螺異三聚茚、呋喃、苯並呋喃、異苯並呋喃、二苯並呋喃、噻吩、苯並噻吩、異苯並噻吩、二苯並噻吩、吡咯、吲哚、異吲哚、咔唑、吡啶、喹啉、異喹啉、吖啶、啡啶、苯並-5,6-喹啉、苯並-6,7-喹
啉、苯並-7,8-喹啉、啡噻、啡噁、吡唑吲唑、咪唑、苯並咪唑、萘並咪唑(naphthimidazole)、菲並咪唑(phenanthrimidazole)、吡啶並咪唑(pyridimidazole)、吡並咪唑(pyrazinimidazole)、喹噁啉並咪唑(quinoxalinimidazole)、噁唑、苯並噁唑、萘並噁唑(naphthoxazole)、蒽並噁唑(anthroxazole)、菲並噁唑(phenanthroxazole)、異噁唑、1,2-噻唑、1,3-噻唑、苯並噻唑、嗒、六氮雜聯伸三苯、苯並嗒、嘧啶、苯並嘧啶、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、啡、啡噁、啡噻、熒紅環(fluorubin)、啶、氮雜咔唑、苯並咔啉、啡啉、1,2,3-三唑、1,2,4-三唑、苯並三唑、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、1,2,4-三、1,2,3-三、四唑、1,2,4,5-四、1,2,3,4-四、1,2,3,5-四、嘌呤、喋啶、吲和苯並噻二唑或衍生自這些系統的組合之基團。
在本發明之一較佳實施態樣中,每環最多一個A基團代表N及其它A基團代表CR1。A特佳代表CR1,致使式(1)化合物為下式(1a)之化合物
其中所使用之符號具有上述所給定之意義,且n在每次出現時相同或不同地代表0、1、2或3。
在本發明之一較佳實施態樣中,式(1a)中之標號n在每次出現時相同或不同地為0、1或2,特佳地,為0或1且非常特佳地等於0。
式(1a)的較佳實施態樣為下式(1b)至(1f)之化合物,
其中所使用之符號具有上述所給定之意義。
特佳實施態樣為下式(1g)之化合物,
其中所使用之符號具有上述所給定之意義。
HetAr基團的較佳實施態樣描述如下。
式(2)、(3)和(4)之基團的較佳實施態樣為下式(2-1)至(2-10)、(3-1)和(4-1)之基團,
其中虛線鍵表示此等基團的鍵聯且R2具有上述所給定之意義。
較佳者為式(2-1)至(2-3)之基團,且特佳者為式(2-1)之基團。
上述基團的較佳實施態樣為下式(2-1a)至(4-1a)之基團,
其中虛線鍵表示此等基團的鍵聯且R2表示根據上述所給定之非氫的定義之取代基。
HetAr基團上之R2取代基較佳在每次出現時相同或不同地為H或具有6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R5基團取代)。式(2-1a)至(4-1a)之基團中的R2在此不等於氫。芳族或雜芳族環系統較佳具有6至18個芳族環原子。特佳的是具有6至12個芳族環原子之芳族環系統或具有6至13個芳族環原子之雜芳族環系統,彼等各自可經一或多個R5基團取代,但較佳為未經取代。適當R2基團的實例係選自由下列所組成群組:苯基、聯苯基(特別是鄰-、間-或對-聯苯基)、聯三苯基(特別是支鏈聯三苯基)、聯四苯基(特別是支鏈聯四苯基)、1-、2-、3-或4-茀基、1-、2-、3-或4-螺聯茀基、吡啶基、嘧啶基、1-、2-、3-或4-二苯並呋喃基、1-、2-、3-或4-二苯並噻吩基和1-、2-、3-或4-咔唑基,彼等各自
可經一或多個R5基團取代,但較佳為未經取代。
適當R2基團的實例為下示之結構R2-1至R2-18,
N1基團的較佳實施態樣係顯示如下。如上所述,N1基團代表式(5)或(6)之基團。
在本發明之一較佳實施態樣中,式(5)之基團中的Ar1基團在每次出現時相同或不同地代表具有6至24個芳族環原子(較佳具有6至18個芳族環原子)之芳族或雜芳族環系統,特佳代表具有6至12個芳族環原子之芳族環系統或具有6至13個芳族環原子之雜芳族環系統,彼等各自可經一或多個R3基團取代,但較佳為未經取代。適當Ar1基團的實例係選自由下列所組成群組:苯基、聯苯基(特別是鄰-、間-或對-聯苯基)、聯三苯基(特別是支鏈聯三苯基)、聯四苯基(特別是支鏈聯四苯基)、1-、2-、3-或4-茀基、1-、2-、3-或4-螺聯茀基、吡啶基、嘧啶基、1-、2-、3-或4-二苯並呋喃基、1-、2-、3-或4-二苯並噻吩基和1-、2-、3-或4-咔唑基,彼等各自可經一或多個R3
基團取代,但較佳為未經取代。
特佳Ar1基團為下式(Ar1-1)至(Ar1-20)之基團,
在本發明之一較佳實施態樣中,R3在每次出現時相同或不同地代表H、具有1至4個C原子之烷基或具有5至14個芳族環原子之芳族或雜芳族環系統。R3特佳在每次出現時相同或不同地代表H或具有1至4個碳原子之烷基。
在式(6)之基團中,較佳的是:若最多一個A基團代表N和其他A基團代表CR1。特佳地,式(6)中之所有A基團代表CR1。式(6)之特佳基團因此為下式(6-1)和(6-2)之基團,
其中R1具有上述所給定之意義且此外:二個相鄰的W基團一起代表下式(7a)或(8a)之基團及其它二個W基團代表CR1且較佳地代表CH,
其中Y2、Y3和R1具有上述所給定之意義;m 在每次出現時相同或不同地為0、1、2、3或4。
在本發明之一較佳實施態樣中,標號m代表0、1、2或3,特佳地代表0、1或2且非常特佳地代表0或1。
式(6-1)之基團的較佳實施態樣為下式(6-1a)至(6-1f)之基團,
其中Y2具有上述所給定之意義且較佳地代表NR4、O或S。
式(6-2)之基團的較佳實施態樣為下式(6-2a)至(6-2f)之基團,
在本發明另一較佳實施態樣中,Y2和Y3在每次出現時相同或不同地代表O、C(R4)2或NR4,其中鍵結至氮之R4基團不等於H,特佳地代表C(R4)2或NR4,其中鍵結至氮之R4基團不等於H,且非常特佳代表C(R4)2。
若Y2或Y3代表NR4,較佳的是:若此R4基團在每次出現時相同或不同地代表具有5至24個芳族環原子之芳族或雜芳族環系統(其在各情況下可經一或多個R5基團取代),特佳代表具有6至18個芳族環原子之芳族或雜芳族環系統(其可經一或多個R5基團取代)。適當R4基團的實例係選自由下列所組成群組:苯基、聯苯基(特別是鄰-、間-或對-聯苯基)、聯三苯基(特別是支鏈聯三苯基)、聯四苯基(特別是支鏈聯四苯基)、1-、2-、3-或4-茀基、1-、2-、3-或4-螺聯茀基、吡啶基、嘧啶基、1,3,5-三基、4,6-二苯基-1,3,5-三基、1-、2-、3-或4-二苯並呋喃基、1-、2-、3-或4-二苯並噻吩基和1-、2-、3-或4-咔唑基,其中咔唑基在氮原子上經非H或D之R5基團取代。此等基團各自可經一或多個R5基團取代,但較佳為未經取代。適當R4取代基為與上述R2-1至R2-18相同的結構。
若Y2代表C(R4)2,較佳的是:若此等R4基團在每次出現時相同或不同地為代表具有1至10個C原子之直鏈烷基或具有3至10個C原子之支鏈或環狀烷基或具有2至10個C原子之烯基(彼等各自可經一或多個R5基團取代,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),或代表具有5至24個芳族環原子之芳族或雜芳族環系統,其在各情況下可經一或多個R5基團取代;二個取代基R4在此可隨意地形成單或多環的脂族、芳族或雜芳族環系統(其可經一或多個R5基團取代)。若R4基團代表苯基,則二個R4取代基的環形成形成螺系統,例如螺聯茀或螺聯茀之衍生物。
在本發明另一較佳實施態樣中,L代表單鍵或具有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R1基團取代)。L特佳在每次出現時相同或不同地代表單鍵或具有6至12個芳族環原子之芳族環系統或具有6至13個芳族環原子之雜芳族環系統,彼等各自可經一或多個R1基團取代,但較佳為未經取代。L非常特佳地代表單鍵。適當芳族或雜芳族環系統L的實例係選自由下列所組成群組:伸苯基、聯苯、茀、吡啶、嘧啶、三、二苯並呋喃、二苯並噻吩和咔唑,彼等各自可經一或多個R1基團取代,但較佳為未經取代。
若根據本發明之化合物含有R1取代基,則此等基團較佳選自由下列所組成群組:H、D、F、CN、N(Ar2)2、C(=O)Ar2、P(=O)(Ar2)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原子之支鏈或環狀烷基或烷氧基或具有2至10個C原子之烯基(彼等各自可經一或多個R5基團取代,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24個芳族環原子之芳族或雜芳族環系統(其在各情況下可經一或多個R5基團取代)、或具有5至25個芳族環原子之芳烷基或雜芳烷基(其可經一或多個R1基團取代);鍵結至相鄰碳原子之二個R1取代基在此可隨意地形成單環或多環的脂肪族環系統(其可經一或多個R5基團取代)。
R1取代基特佳係選自由下列所組成群組:H、D、F、CN、N(Ar2)2、具有1至8個C原子(較佳具有1、2、3或4個C原子)之直鏈烷基、或具有3至8個C原子(較佳具有3或4個C原子)之支鏈或環狀烷基、或具有2至8個C原子(較佳具有2、3或4個C原子)之烯基(彼等各自可經一或多個R5基團取代,但較佳為未經取代)、或具有6至24個芳族環原子(較佳具有6至18個芳族環原子,特佳具有6至13個芳族環原子)之芳族或雜芳族環系統(其在各情況下可經一或多個非芳族R5基團取代,但較佳為未經取代);鍵結至相鄰碳原子之二個R1取代基在此可隨意地形成單環或多環的脂肪族環系統(其可經一或多個R5基團取代,但較佳為未經取代)。
R1取代基非常特佳係選自由下列所組成群組:H或具有6至18個芳族環原子(較佳具有6至13個芳族環原子)之芳族或雜芳族環系統,其在各情況下可經一或多個非芳
族R5基團取代,但較佳為未經取代。適當R1取代基的實例係選自由下列所組成群組:苯基、聯苯基(特別是鄰-、間-或對-聯苯基)、聯三苯基(特別是支鏈聯三苯基)、聯四苯基(特別是支鏈聯四苯基)、1-、2-、3-或4-茀基、1-、2-、3-或4-螺聯茀基、吡啶基、嘧啶基、1-、2-、3-或4-二苯並呋喃基、1-、2-、3-或4-二苯並噻吩基和1-、2-、3-或4-咔唑基,彼等各自可經一或多個R5基團取代,但較佳為未經取代。適當R1結構在此為與上述R2-1至R2-18相同之結構。
在本發明另一較佳實施態樣中,R5在每次出現時相同或不同地選自由下列所組成之群組:H、D、F、CN、具有1至10個C原子(較佳具有1、2、3或4個C原子)之脂族烴基、或具有5至30個芳族環原子(較佳具有5至13個芳族環原子)之芳族或雜芳族環系統,其可經一或多個各自具有1至4個碳原子之烷基取代,但較佳為未經取代。
若根據本發明之化合物係經芳族或雜芳族基取代,則較佳的是:若此等化合物不含具有二個以上之芳族六員環彼此直接縮合的芳基或雜芳基。取代基特佳絕對不含具有彼此直接縮合之六員環的芳基或雜芳基。此較佳撰擇是由於此等結構的低三重態能。根據本發明仍亦適合的具有二個以上之芳族六員環彼此直接縮合的縮合芳基為菲和三伸苯基,因為此等也具有高三重態能階。
上述的較佳選擇可個別發生或一起發生。較佳的是:
若上述的較佳選擇一起發生。
較佳者因此為上述式(1a)之化合物,其中:L 在每次出現時相同或不同地為單鍵或具有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R1基團取代;HetAr 為上述式(2-1)至(2-10)、(3-1)或(4-1)中之一者的基團;N1 為下式(5)、(6-1)或(6-2)之基團,
二個相鄰的W基團一起代表下式(7a)或(8a)之基團及其它W基團代表CR1且較佳地代表CH,
Ar1 在每次出現時相同或不同地為具有6至24個芳族環原子(較佳具有6至18個芳族環原子)之芳族或雜芳族環系統,其可經一或多個R3基團取代;Y2、Y3在每次出現時相同或不同地為O、NR4或C(R4)2,其中鍵結至N之R4基團不等於H;R1 在每次出現時相同或不同地選自由下列所組成之群組:H、D、F、CN、N(Ar2)2、
C(=O)Ar2、P(=O)(Ar2)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原子之支鏈或環狀烷基或烷氧基或具有2至10個C原子之烯基(彼等各自可經一或多個R5基團取代,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24個芳族環原子之芳族或雜芳族環系統(其在各情況下可經一或多個R5基團取代)、或具有5至25個芳族環原子之芳烷基或雜芳烷基(其可經一或多個R1基團取代);鍵結至相鄰碳原子之二個R1取代基在此可隨意地形成單環或多環的脂肪族環系統(其可經一或多個R5基團取代);R2 在每次出現時相同或不同地為H或具有6至24個芳族環原子(特別是具有6至18個芳族環原子)之芳族或雜芳族環系統,其在各情況下可經一或多個R5基團取代;R3 在每次出現時相同或不同地為H、具有1至4個碳原子之烷基或具有5至14個芳族環原子之芳族或雜芳族環系統;R4 當Y2或Y3=NR4時,為具有5至24個芳族環原子(較佳具有6至18個芳族環原子)之芳族或雜芳族環系統,其在各情況下可經一或多個R5基團取代;
及當Y2或Y3=C(R4)2時,在每次出現時相同或不同地為具有1至10個C原子之直鏈烷基或具有3至10個C原子之支鏈或環狀烷基或具有2至10個C原子之烯基(彼等各自可經一或多個R5基團取代,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)、或具有5至24個芳族環原子之芳族或雜芳族環系統,其在各情況下可經一或多個R5基團取代;二個取代基R4在此可隨意地形成單-或多環的脂族、芳族或雜芳族環系統(其可經一或多個R5基團取代);R5 在每次出現時相同或不同地選自由下列所組成之群組:H、D、F、CN、具有1至10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,其可經一或多個各自具有1至4個碳原子之烷基取代;n 在每次出現時相同或不同地為0、1、2或3,較佳為0、1或2;m 在每次出現時相同或不同地為0、1、2、3或4,較佳為0、1、2或3;其它符號具有上述所給定之意義。
特佳者為上述式(1b)至(1g)之化合物,其中:L 在每次出現時相同或不同地為單鍵或具有6至12個芳族環原子之芳族環系統或具有6至13
個芳族環原子之雜芳族環系統,彼等各自可經一或多個R1基團取代,但較佳為未經取代;HetAr 為上述(2-1a)至(2-10a)、(3-1a)或(4-1a)中之一者的基團;N1 上述式(5)、(6-1)或(6-2a)至(6-2f)之基團;Ar1 在每次出現時相同或不同地選自由下列所組成之群組:苯基、聯苯基、聯三苯基、聯四苯基、1-、2-、3-或4-茀基、1-、2-、3-或4-螺聯茀基、吡啶基、嘧啶基、1-、2-、3-或4-二苯並呋喃基、1-、2-、3-或4-二苯並噻吩基和1-、2-、3-或4-咔唑基,彼等各自可經一或多個R基團取代,但較佳為未經取代,且特佳係選自上述式(Ar1-1)至(Ar1-20)之基團;Y2、Y3在每次出現時相同或不同地為NR4或C(R4)2,其中鍵結至N之R4基團不等於H,且特別是C(R4)2;R1 在每次出現時相同或不同地選自由下列所組成之群組:H、D、F、CN、N(Ar2)2、具有1至8個C原子(較佳具有1、2、3或4個C原子)之直鏈烷基、或具有3至8個C原子(較佳具有3或4個C原子)之支鏈或環狀烷基、或具有2至8個C原子(較佳具有2、3或4個C原子)之烯基(彼等各自可經一或多個R5基團取代,但較佳為未經取代)、或具有6至24個
芳族環原子(較佳具有6至18個芳族環原子,特佳具有6至13個芳族環原子)之芳族或雜芳族環系統(其在各情況下可經一或多個非芳族R5基團取代,但較佳為未經取代);鍵結至相鄰碳原子之二個R1取代基在此可隨意地形成單環或多環的脂肪族環系統(其可經一或多個R5基團取代,但較佳為未經取代);R1特佳在每次出現時相同或不同地選自由下列所組成之群組:H或具有6至18個芳族環原子(較佳具有6至13個芳族環原子)之芳族或雜芳族環系統,其在各情況下可經一或多個非芳族R5基團取代,但較佳為未經取代;R2 在每次出現時相同或不同地選自由下列所組成之群組:苯基、聯苯基、聯三苯基、聯四苯基(特別是支鏈聯四苯)、1-、2-、3-或4-茀基、1-、2-、3-或4-螺聯茀基、吡啶基、嘧啶基、1-、2-、3-或4-二苯並呋喃基、1-、2-、3-或4-二苯並噻吩基和1-、2-、3-或4-咔唑基,彼等各自可經一或多個R5基團取代,且特佳係選自上述結構R2-1至R2-18之基團;R3 為H或具有1至4個C原子之烷基;R4 當Y2或Y3=NR4時,係選自由下列所組成群組:苯基、聯苯基、聯三苯基、聯四苯基、1-、2-、3-或4-茀基、1-、2-、3-或4-螺聯茀
基、吡啶基、嘧啶基、1,3,5-三基、4,6-二苯基-1,3,5-三基、1-、2-、3-或4-二苯並呋喃基、1-、2-、3-或4-二苯並噻吩基和1-、2-、3-或4-咔唑基,其中咔唑基在氮原子上經非H或D之R5基團取代,其中此等基團各自可經一或多個R5基團取代;特佳者為上述結構R2-1至R2-18;及當Y2或Y3=C(R4)2時,在每次出現時相同或不同地為具有1至5個C原子之直鏈烷基或具有3至8個C原子之支鏈或環狀烷基或具有2至8個C原子之烯基(彼等各自可經一或多個R5基團取代,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)、或具有6至18個芳族環原子之芳族或雜芳族環系統(其在各情況下可經一或多個R5基團取代);二個取代基R4在此可隨意地形成單-或多環的脂族、芳族或雜芳族環系統(其可經一或多個R5基團取代):R5 在每次出現時相同或不同地選自由下列所組成之群組:H、D、F、CN、具有1、2、3或4個C原子之脂族烴基或具有5至13個芳族環原子之芳族或雜芳族環系統,其可經一或多個各自具有1至4個碳原子之烷基取代,但較佳為未經取代;
n 在每次出現時相同或不同地為0或1;m 在每次出現時相同或不同地為0、1或2,較佳為0或1。其它符號具有上述所給定之意義。
根據本發明之適當化合物的實例為下示結構。
根據本發明之化合物可藉由熟習該項技術者已知的合成步驟(諸如,例如溴化、鈴木(Suzuki)偶合、烏爾曼(Ullmann)偶合、哈特維希-布赫瓦爾德(Hartwig-Buchwald)偶合、等等)製備。適當合成方法係籠統描述於下述流程1中。
合成從1-鹵二苯並呋喃或-二苯並噻吩開始,彼等可轉化成對應硼酸或硼酸衍生物。在下一步驟中,可藉由鈴木偶合引入HetAr基團。鹵化(例如使用NBS)選擇性發生於二苯並呋喃或二苯並噻吩之8-位置。在最後步驟中,N1
基團可(例如)藉由特維希-布赫瓦爾德偶合引入於此位置。
所示用於合成根據本發明化合物之一般方法是示例性的。熟習該項技術者在其一般專業知識的範圍內將能夠開發替代性合成路徑。
本發明因此此外關於一種合成根據本發明化合物之方法,其從1-鹵二苯並呋喃或1-鹵二苯並噻吩開始,其中鹵素較佳為溴,其特徵在於下列步驟:(1)隨意地將鹵素基團轉化成硼酸或硼酸衍生物;(2)藉由偶合反應(特別是鈴木偶合)引入HetAr基團;(3)二苯並呋喃或二苯並噻吩於8-位置之鹵化,特別是溴化;(4)藉由偶合反應(特別是哈特維希-布赫瓦爾德偶合)引入N1基團。
為了從液相處理根據本發明之化合物(例如藉由旋轉塗佈或藉由印刷方法)需要根據本發明之化合物的調配物。此等調配物可為例如溶液、分散液或乳液。為此目的,較佳可為使用二或多種溶劑之混合物。適當且較佳的溶劑為(例如)甲苯、苯甲醚、鄰-、間-或對-二甲苯、苯甲酸甲酯、對稱三甲苯、四氫萘、藜蘆醚、THF、甲基-THF、THP、氯苯、二噁烷、苯氧基甲苯(特別是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-甲基苯並噻唑、2-苯氧基乙醇、2-吡咯啶酮、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、苯並噻唑、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、茚烷、苯甲酸甲酯、NMP、對-異丙基甲苯、苯基乙基醚、1,4-二異丙基苯、二苄基醚、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。
本發明因此此外關於一種調配物,其包含根據本發明之化合物和至少一種另外的化合物。另外的化合物可為(例如)溶劑,特別是上述溶劑中之一者或此等溶劑之混合物。然而,另外的化合物也可為至少一種同樣可用於電子裝置之另外的有機或無機化合物,例如發光化合物(特別是磷光摻雜劑)及/或另外的基質材料。適當發光化合物和另外的基質材料如下所示與有機電激發光裝置有關者。此另外的化合物也可為聚合的。
根據本發明之化合物和混合物係適合使用於電子裝置。電子裝置在此意指一種包含至少一個包含至少一種有機化合物之層的裝置。然而,該元件在此亦可包含無機材料或完全由無機材料構建之層。
本發明因此此外關於根據本發明之化合物或混合物於電子裝置(特別是於有機電激發光裝置)之用途。
本發明此外又關於一種包含上述根據本發明之化合物
或混合物中的至少一者之電子裝置。上述就化合物而言之較佳陳述亦適用於電子裝置。
電子裝置較佳係選自由下列所組成之群組:有機電激發光裝置(OLED、PLED)、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)、有機染料敏化的太陽能電池、有機光學檢測器、有機感光器、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)和“有機電漿發光裝置(organic plasmon emitting device)”(D.M.Koller等人,Nature Photonics 2008,1-4),較佳為有機電激發光裝置(OLED、PLED),特別是磷光OLED。
有機電激發光裝置包含陽極、陰極及至少一個發光層。除了此等層以外,有機電激發光裝置亦可包含其它層,例如在各情況下一或多個電洞注入層、電洞傳輸層、電洞阻擋層、電子傳輸層、電子注入層、激子阻擋層、電子阻擋層、及/或電荷產生層。同樣可能在二個發光層之間引入具有(例如)激子阻擋功能之中間層。然而,應指出的是此等層不一定必須存在。有機電激發光裝置在此可包含一個發光層或多個發光層。若存在多個發光層,則此等較佳地具有總計多個在380奈米與750奈米之間的發光最大值,整體導致為白色發光,亦即將能夠發螢光或磷光的各種發光化合物使用於發光層中。特佳者為具有三個發光層之系統,其中該三層呈現藍色、綠色及橙色或紅色發光
(基本結構參見例如WO 2005/011013)。此等可為螢光或磷光發光層或其中螢光和磷光發光層彼此合併的混合系統。
根據上示實施態樣的根據本發明之化合物可使用於各種層中,取決於精確結構。較佳者為一種有機電激發光裝置,其包含式(1)或根據較佳實施態樣之化合物作為用於螢光或磷光發光體(特別是用於磷光發光體)、及/或電子傳輸層中及/或電子阻擋或激子阻擋層中及/或電洞傳輸層中之基質材料,取決於精確取代。上示較佳實施態樣也適用於材料在有機電子裝置中之用途。
在本發明之一較佳實施態樣中,式(1)或根據較佳實施態樣之化合物係用作發光層中之螢光或磷光化合物(特別是磷光化合物)之基質材料。有機電激發光裝置在此可包含一個發光層或多個發光層,其中至少一個發光層包含至少一種根據本發明之化合物作為基質材料。
若式(1)或根據較佳實施態樣之化合物係用作發光層中的發光化合物之基質材料,則較佳與一或多種磷光材料(三重態發光體)組合使用。磷光就本發明的意義而言意指從具有自旋多重性>1之激態(特別是從激發之三重態)的發光(luminescence)。為了本申請案之目的,所有發光過渡金屬錯合物和發光鑭族元素錯合物(特別是所有銥、鉑和銅錯合物)係視為磷光化合物。
包含式(1)或根據較佳實施態樣之化合物和發光化合物的混合物以包含發光體和基質材料的整個混合物為基準計,包含介於99和1體積%之間,較佳介於98和10體
積%之間,特佳介於97和60體積%之間,特別是介於95和80體積%之間的式(1)或根據較佳實施態樣之化合物。對應地,混合物以包含發光體和基質材料的整個混合物為基準計,包含介於1和99體積%,較佳地介於2和90體積%之間,特佳地介於3和40體積%之間,特別是介於5和20體積%之間的發光體。
本發明之另一較佳實施態樣為式(1)或根據較佳實施態樣之化合物與另外的基質材料組合用於磷光發光體之基質材料的用途。可與式(1)或根據較佳實施態樣之化合物組合使用的特別適合之基質材料為芳族酮、芳族氧化膦或芳族亞碸或碸(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或WO 2008/086851中所揭示之咔唑衍生物)、吲哚並咔唑衍生物(例如根據WO 2007/063754或WO 2008/056746)、茚並咔唑衍生物(例如,根據WO 2010/136109或WO 2011/000455)、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)、氮硼雜環戊烯(azaborole)或硼酸酯(例如根據WO 2006/117052)、三衍生物(例如根據WO 2010/015306、WO 2007/063754或WO 2008/056746)、鋅錯合物(例如根據EP 652273或
WO 2009/062578)、二氮雜矽雜環戊二烯(diazasilole)或四氮雜矽雜環戊二烯衍生物(例如根據WO 2010/054729)、二氮磷雜環戊二烯(diazaphosphole)衍生物(例如根據WO 2010/054730)、橋聯咔唑衍生物(例如根據US 2009/0136779、WO 2010/050778、WO 2011/042107、WO 2011/088877或根據尚未公開的申請案EP 11003232.3)、聯伸三苯衍生物(例如,根據WO 2012/048781)、或內醯胺(例如,根據WO 2011/116865或WO 2011/137951)。在比實際發光體短的波長發光之另外磷光發光體同樣可存在於混合物中作為共主體。
較佳共主體材料為三芳基胺衍生物,特別是單胺、內醯胺、咔唑衍生物和茚並咔唑衍生物。
適當磷光化合物(=三重態發光體)特別為在適當激發時發光(較佳在可見光區域內)且另外含有至少一種具有原子序大於20(較佳為大於38且少於84,特佳為大於56且少於80)的原子之化合物,特別是具有此原子序的金屬。所使用之磷光發光體較佳為含有銅、鉬、鎢、錸、釕、鋨、銠、銥、鈀、鉑、銀、金或銪的化合物,特別是含有銥或鉑的化合物。就本發明之目的而言,含有上述金屬之發光化合物全部被視為磷光化合物。
上述發光體的實例係由申請案WO 00/70655、WO 2001/41512、WO 2002/02714、WO 2002/15645、EP 1191613、EP 1191612、EP 1191614、WO 05/033244、WO 05/019373、US 2005/0258742、WO 2009/146770、WO
2010/015307、WO2010/031485、WO2010/054731、WO 2010/054728、WO 2010/086089、WO 2010/099852、WO 2010/102709、WO 2011/032626、WO 2011/066898、WO 2011/157339、WO 2012/007086、WO 2014/008982、WO 2014/023377、WO 2014/094962、WO 2014/094961或WO 2014/094960披露。通常,如根據先前技術用於磷光OLED且為熟習有機電激發光裝置領域之技術者已知的所有磷光錯合物皆適合,且熟習該項技術者也將能夠在無進步性下使用另外的磷光錯合物。
在本發明另一實施態樣中,根據本發明的有機電激發光裝置不包含單獨的電洞注入層及/或電洞傳輸層及/或電洞阻擋層及/或電子傳輸層,亦即發光層直接與電洞注入層或陽極相鄰,及/或發光層直接與電子傳輸層或電子注入層或陰極相鄰,如例如在WO 2005/053051中所述。此外可能使用與發光層中之金屬錯合物相同或類似的金屬錯合物作為直接與發光層相鄰之電洞傳輸或電洞注入材料,如(例如)WO 2009/030981中所述。
此外根據本發明之化合物可能使用於電洞阻擋或電子傳輸層。此特別適用於不含咔唑結構的根據本發明之化合物。此等較佳亦可經一或多個另外的電子傳輸基(例如苯並咪唑基)取代。
在根據本發明之有機電激發光裝置的另外層中,可能採用如根據先前技術通常所使用之所有材料。熟習該項技術者因此將能夠在無進步性下使用有機電激發光裝置的已
知所有材料與式(1)或根據較佳實施態樣之化合物組合。
此外較佳者為一種有機電激發光裝置,其特徵在於利用昇華方法施加一或多層,其中該等材料係於真空昇華單元中在低於10-5毫巴,較佳低於10-6毫巴之初壓力下藉由氣相沈積施加。然而,初壓力在此也可能甚至更低或更高,例如低於10-7毫巴。
同樣較佳者為一種有機電激發光裝置,其特徵在於利用OVPD(有機蒸氣相沈積)法或輔以載體-氣體昇華法施加一或多層,其中該等材料係在介於10-5毫巴與1巴之間的壓力下施加。此方法的一特殊例子為OVJP(有機蒸氣噴墨印刷)方法,其中該等材料係經由噴嘴直接施加且因此結構化(例如,M.S.Arnold等人之Appl.Phys.Lett.2008,92,053301)。
此外較佳者為一種有機電激發光裝置,其特徵在於諸如(例如)以旋轉塗佈或利用任何所欲印刷方法(諸如,例如噴墨印刷、LITI(光誘導熱成像、熱轉移印刷)、網版印刷、快乾印刷、平版印刷或噴嘴印刷)從溶液製造一或多層。為此目的需要可溶性化合物,其可藉由適當取代而獲得。
也可能者為混合方法,其中,例如,一或多層從溶液施加和一或多個另外的層係藉由氣相沈積施加。因此,例如,可能從溶液施加發光層及藉由氣相沈積施加電子傳輸層。
這些方法通常為熟習該項技術者已知的且熟習該項技
術者可在無進步性下施用於包含根據本發明化合物之有機電激發光裝置。
根據本發明之化合物通常在使用於有機電激發光裝置時具有非常良好的性質。特別是,相較於根據先前技術之類似化合物,根據本發明之化合物在使用於有機電激發光裝置時的壽命顯著較好。有機電激發光裝置的其它性質(特別是效率和電壓)也同樣較好或至少相當。此外,化合物具有高玻璃轉移溫度和高熱穩定性。
現在將藉由下列實施例更詳細地闡釋本發明,但不希望因此限制本發明。
除非另外指出,否則在保護性氣體氛圍下於乾燥溶劑中進行下列合成。溶劑和試劑可購買自例如Sigma-ALDRICH或ABCR。對應CAS號碼在各情況下也指示來自從文獻得知的化合物。
將200g(664mmol)的1-溴-3-氟-2-碘苯、101g(664mmol)的2-甲氧基苯基硼酸和137.5g(997mmol)的四硼酸鈉溶解在1000ml的THF和600ml的水中並除氣。添加
9.3g(13.3mmol)的氯化雙(三苯基膦)鈀(II)和1g(20mmol)的氫氧化肼。接著將反應混合物在保護性氣體氛圍下於70℃攪拌48h。將冷卻溶液用甲苯補充,用水洗滌數次,乾燥和蒸發。藉由管柱層析法在矽膠上用甲苯/庚烷(1:2)純化產物。產量:155g(553mmol),理論的83%。
類似地製備下列化合物:
將112g(418mmol)的6-溴-2-氟-2’-甲氧基聯苯溶解
在2l的二氯甲烷中並冷卻至5℃。經90min.的過程將41.01ml(431mmol)的三溴化硼滴加至此溶液,並繼續攪拌過夜。將水慢慢地加至混合物,並將有機相用水洗滌三次,經過Na2SO4乾燥,在旋轉蒸發器中蒸發並藉由層析法純化。產量:104g(397mmol),理論的98%。
類似地製備下列化合物:
將111g(416mmol)的6’-溴-2’-氟聯苯-2-醇溶解在2l的SeccoSolv® DMF(max.0.003%的H2O)中並冷卻至5℃。將20g(449mmol)的氫化鈉(在石蠟油中之60%懸浮液)分批加至溶液,且加入完成之後將混合物攪拌另20
min,接著在100℃下加熱45min。冷卻之後,將500ml的乙醇慢慢地加至混合物,其然後在旋轉蒸發器中蒸發至乾且藉由層析法純化。產量:90g(367mmol),理論的88.5%。
類似地製備下列化合物:
將180g(728mmol)的1-溴二苯並呋喃溶解在1500ml的乾燥THF中並冷卻至-78℃。在此溫度下經約5min.的過程添加305ml(764mmol/在己烷之2.5M)的正丁基鋰,並接著在-78℃下繼續攪拌2.5h。在此溫度下盡可能迅速地添加151g(1456mmol)的硼酸三甲酯,及使反應混合物
慢慢地至室溫(約18h)。用水洗滌反應溶液,及將沈澱的固體和有機相與甲苯共沸地乾燥。藉由在約40℃下與甲苯/二氯甲烷一起攪拌而將粗製產物洗滌並以抽吸濾出。產量:146g(690mmol),理論的95%。
類似地製備下列化合物:
將23g(110.0mmol)的二苯並呋喃-1-硼酸、29.5g(110.0mmol)的2-氯-4,6-二苯基-1,3,5-三和21g(210.0mmol)的碳酸鈉懸浮在500ml的乙二醇二胺醚和500ml的水中。將913mg(3.0mmol)的三-鄰甲苯基膦及接著
112mg(0.5mmol)的乙酸鈀(ii)加至此懸浮液,並將反應混合物在回流下加熱16h。冷卻之後,將有機相分離出來,通過矽膠過濾,每次用200ml的水洗滌三次且隨後蒸發至乾。將殘餘物從甲苯和從二氯甲烷/庚烷再結晶。產量為37g(94mmol),對應於理論的87%。
類似地製備下列化合物:
將70g(190.0mmol)的2-二苯並呋喃-1-基-4,6-二苯基-1,3,5-三懸浮在2000ml的乙酸(100%)和2000ml的硫酸(95-98%)中。將34g(190mmol)的NBS加至此懸浮液,並將混合物在黑暗中攪拌2h。接著添加水/冰,並將固體分離出來及用乙醇沖洗。從甲苯再結晶殘餘物。產量為80g(167mmol),對應於理論的87%。
類似地製備下列化合物:
在噻吩衍生物的情況下,使用硝基苯代替硫酸及使用元素溴代替NBS:
將70g(147mmol)的2-(8-溴二苯並呋喃-1-基)-4,6-二苯基-1,3,5-三和35.7g(147mmol)的3-苯基-9H-咔唑在600ml的甲苯中之除氣溶液以N2飽和1h。首先將2.09ml(8.6mmol)的P(tBu)3,接著1.38g(6.1mmol)的乙酸鈀(II)加至該溶液,及隨後添加固態17.7g(185mmol)的NaOtBu。將反應混合物在回流下加熱1h。在冷卻至室溫之後,將混合物用3×50ml的甲苯洗滌。經過MgSO4乾燥,且在真空中移除溶劑。藉由層析在矽膠上用庚烷/乙酸乙酯(20/1)純化粗製產物。將殘餘物從甲苯再結晶且最後在高真空(p=5×10-6毫巴)中昇華。產量為74.8g(116
mmol),對應於理論的80%。
類似地製備下列化合物:
最初將24.0g(142mmol,1.2eq.)的4-胺基聯苯(CAS 92-67-1)與32.0g(117mmol,1.0eq.)的2-溴-9,9’-二甲基茀(CAS 28320-31-2)一起引入950ml的甲苯中並以氬氣飽和30分鐘。接著添加1.0g(1.8mmol,0.02eq.)的1,1’-雙(二苯膦基)二茂鐵(CAS 12150-46-8)、350mg(1.6mmol,0.01eq.)的乙酸鈀(II)(CAS 3375-31-3)和29g(300mmol,2.6eq.)的第三丁醇鈉(CAS 865-48-5),並將混合物在回流下加熱過夜。當反應完全時,將該批料用300ml的甲苯稀釋並用水萃取。將有機相經硫酸鈉乾燥,且在旋轉蒸發
器中移除溶劑。將50毫升乙酸乙酯添加至棕色油中,且將混合物加至庚烷/乙酸乙酯20:1的混合物中。將所形成的固體以抽氣濾出且以庚烷洗滌。乾燥產生29g(80mmol,69%)的所要產物h,具有99.1%之HPLC純度。
類似地製備下列化合物:
類似於上述g)項所指示之步驟製備下列化合物:
在下列實施例V1至E20中呈現各種OLED之數據(參見表1和2)。
實施例V1-E20之預處理:將已塗有厚度為50nm之結構化ITO(氧化銦錫)的玻璃板塗佈20nm之PEDOT:PSS(聚(3,4-伸乙基二氧基噻吩)聚(苯乙烯磺酸酯),以CLEVIOSTM P VP AI 4083自德國Heraeus Precious Metals GmbH購得,藉由旋轉塗佈自水溶液施加)以改良處理。此等經塗覆玻璃板形成施加OLED之基板。
OLED原則上具有下列的層結構:基板/電洞傳輸層
(HTL)/隨意中間層(IL)/電子阻擋層(EBL)/發光層(EML)/隨意電洞阻擋層(HBL)/電子傳輸層(ETL)/隨意電子注入層(EIL)及最後陰極。陰極係由具有100nm之厚度的鋁陰極形成。OLED的精確結構係顯示於表1中。製造OLED所需的材料係顯示於表3中。
所有材料係在真空室內藉由熱氣相沈積施加。發光層在此總是由至少一種基質材料(主體材料)和發光摻雜劑(發光體)組成,該發光摻雜劑藉由共蒸發而與基質材料或基質材料等以某體積比例摻混。詞句諸如IC1:IC3:TEG1(55%:35%:10%)在此意指材料IC1係以55%之體積比例存在於層中,IC3係以35%之比例存在於層中,和TEG1係以10%之比例存在於層中。類似地,電子傳輸層亦可由二種材料之混合物所組成。
OLED係以標準方法示性。為此目的,測定電激發光光譜、電流效率(以cd/A測量)、功率效率(以lm/W測量)及假設Lambert發光特性,從電流/電壓/發光密度特徵線(IUL特徵線)計算以發光密度為函數之外部量子效率(EQE,以百分比測量)及壽命。電激發光光譜係在1000cd/m2之發光密度下測定,且由此計算CIE 1931 x與y色座標。表2中詞句U1000表示1000cd/m2之發光密度所需之電壓。CE1000及PE1000表示在1000cd/m2下所達到之電流及功率效率。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下操作時自初始發光密度下降至某一比例
L1之後的時間。表2中之L0;j0=4000cd/m2和L1=70%之詞句意指LT欄中所指示之壽命對應於在初始發光密度自4000cd/m2降至2800cd/m2後的時間。類似地,L0;j0=20mA/cm2,L1=80%意指在於20mA/cm2操作時,在時間LT之後,發光密度降至其初始值之80%。
各種OLED之數據係總結於表2中。實施例V1-V5為根據先前技術之OLED比較例,實施例E1至E20顯示根據本發明之OLED的數據。
在下文中更詳細地闡釋一些實施例以說明根據本發明之化合物的優點。
當用作磷光OLED中之基質材料,根據本發明之材料導致超越先前技術之關於元件壽命的顯著改良。觀察到:相較於先前技術,根據本發明之化合物EG1和EG4與綠色-發光摻雜劑TEG1組合使用使壽命能夠增加200%(實施例V1與E1之比較和V2與E2之比較以及V3與E3之比較和V4、V5與E4之比較)。
Claims (14)
- 一種式(1)化合物,
- 根據申請專利範圍第1項之化合物,其為式(1a),
- 根據申請專利範圍第1或2項之化合物,其為式(1b)至(1g)中之一者,
- 根據申請專利範圍第1或2項之化合物,其中式(2)、(3)和(4)之基團係選自式(2-1)至(2-10)、(3-1)和(4-1)之基團,
- 根據申請專利範圍第1或2項之化合物,其中Ar1在每次出現時相同或不同地代表具有6至18個芳族環原子之芳族或雜芳族環系統,其在各情況下可經一或多個R3基團取代。
- 根據申請專利範圍第1或2項之化合物,其中Ar1係相同或不同地選自由下列所組成之群組:苯基、聯苯基、聯三苯基、聯四苯基、茀基、螺聯茀基、吡啶基、嘧啶基、二苯並呋喃基、二苯並噻吩基和咔唑基,彼等各自可經一或多個R3基團取代。
- 根據申請專利範圍第1或2項之化合物,其中式(6)之基團係選自式(6-1)和(6-2)之基團,
- 根據申請專利範圍第1或2項之化合物,其中式(6)之基團係選自式(6-1a)至(6-1f)或(6-2a)至(6-2f)之基團,
- 根據申請專利範圍第1或2項之化合物,其中Y2和Y3在每次出現時相同或不同地代表O、C(R4)2或NR4,其中鍵結至氮之R4基團不等於H。
- 一種製備根據申請專利範圍第1至8項中之一或多項的化合物之方法,其係從1-鹵二苯並呋喃或1-鹵二苯並噻吩開始,其特徵為下列步驟:(1)隨意地將鹵素基團轉化成硼酸或硼酸衍生物; (2)藉由偶合反應引入HetAr基團;(3)二苯並呋喃或二苯並噻吩於8-位置之鹵化,特別是溴化;(4)藉由偶合反應引入N1基團。
- 一種調配物,其包含至少一種根據申請專利範圍第1至8項中一或多項之化合物及至少一種溶劑。
- 一種根據申請專利範圍第1至8項中一或多項之化合物之用途,其係用於電子裝置。
- 一種電子裝置,其包含至少一種根據申請專利範圍第1至8項中一或多項之化合物。
- 根據申請專利範圍第13項之電子裝置,其為有機電激發光裝置,其中根據申請專利範圍第1至11項中一或多項之化合物係用作螢光或磷光發光體及/或電子傳輸層及/或電子阻擋或激子阻擋層及/或電洞傳輸層中之基質材料。
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Cited By (8)
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TWI641606B (zh) * | 2016-11-07 | 2018-11-21 | 南韓商Lg化學股份有限公司 | 化合物以及包含此化合物的有機發光裝置 |
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US11296281B2 (en) | 2017-03-15 | 2022-04-05 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
US11678572B2 (en) | 2016-06-29 | 2023-06-13 | Samsung Sdi Co., Ltd. | Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device and display apparatus |
Families Citing this family (147)
Publication number | Priority date | Publication date | Assignee | Title |
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US10741772B2 (en) * | 2014-08-29 | 2020-08-11 | Samsung Electronics Co., Ltd. | Organic light-emitting device |
JP5831654B1 (ja) | 2015-02-13 | 2015-12-09 | コニカミノルタ株式会社 | 芳香族複素環誘導体、それを用いた有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
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KR101693744B1 (ko) * | 2016-05-11 | 2017-02-06 | 희성소재 (주) | 헤테로고리 화합물 및 이를 이용한 유기 발광 소자 |
KR101849747B1 (ko) * | 2016-07-20 | 2018-05-31 | 주식회사 엘지화학 | 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자 |
WO2018016742A1 (ko) * | 2016-07-20 | 2018-01-25 | 주식회사 엘지화학 | 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자 |
KR102032610B1 (ko) | 2016-07-26 | 2019-10-15 | 주식회사 엘지화학 | 유기 발광 소자 |
JP2019530676A (ja) | 2016-09-14 | 2019-10-24 | メルク パテント ゲーエムベーハー | カルバゾール構造を有する化合物 |
EP3512841B1 (de) | 2016-09-14 | 2023-04-26 | Merck Patent GmbH | Verbindungen mit spirobifluoren-strukturen |
TWI766884B (zh) * | 2016-09-30 | 2022-06-11 | 德商麥克專利有限公司 | 具有二氮雜二苯并呋喃或二氮雜二苯并噻吩結構的化合物、其製法及其用途 |
EP3538521A1 (de) | 2016-11-09 | 2019-09-18 | Merck Patent GmbH | Materialien für organische elektrolumineszenzvorrichtungen |
CN108884086B (zh) * | 2016-11-16 | 2021-10-29 | 株式会社Lg化学 | 杂环化合物及利用其的有机发光元件 |
KR101885898B1 (ko) * | 2016-11-16 | 2018-08-06 | 주식회사 엘지화학 | 유기 발광 소자 |
US11713319B2 (en) | 2016-11-30 | 2023-08-01 | Merck Patent Gmbh | Compounds having valerolactam structures |
EP3548486B1 (de) | 2016-12-05 | 2021-10-27 | Merck Patent GmbH | Materialien für organische elektrolumineszenzvorrichtungen |
TW201831468A (zh) | 2016-12-05 | 2018-09-01 | 德商麥克專利有限公司 | 含氮的雜環化合物 |
EP3548485B1 (de) | 2016-12-05 | 2021-01-20 | Merck Patent GmbH | Materialien für organische elektrolumineszenzvorrichtungen |
JP2020061390A (ja) * | 2016-12-26 | 2020-04-16 | 出光興産株式会社 | 組成物、有機エレクトロルミネッセンス素子用材料、組成物膜、有機エレクトロルミネッセンス素子、及び電子機器 |
KR101857703B1 (ko) * | 2016-12-26 | 2018-05-14 | 주식회사 엘지화학 | 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자 |
JP2020061389A (ja) * | 2016-12-26 | 2020-04-16 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子及び電子機器 |
EP3565816B1 (de) | 2017-01-04 | 2022-03-16 | Merck Patent GmbH | Materialien für organische elektrolumineszenzvorrichtungen |
US10964894B2 (en) | 2017-01-25 | 2021-03-30 | Merck Patent Gmbh | Carbazole derivatives |
EP3573985B1 (de) | 2017-01-30 | 2023-01-18 | Merck Patent GmbH | Materialien für organische elektrolumineszenzvorrichtungen |
TW201835075A (zh) | 2017-02-14 | 2018-10-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置之材料 |
WO2018157981A1 (de) * | 2017-03-02 | 2018-09-07 | Merck Patent Gmbh | Materialien für organische elektronische vorrichtungen |
TW201843143A (zh) | 2017-03-13 | 2018-12-16 | 德商麥克專利有限公司 | 含有芳基胺結構之化合物 |
WO2018174679A1 (ko) * | 2017-03-24 | 2018-09-27 | 희성소재(주) | 유기 발광 소자 및 유기 발광 소자의 유기물층용 조성물 |
WO2018174678A1 (ko) * | 2017-03-24 | 2018-09-27 | 희성소재(주) | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
CN109564973B (zh) * | 2017-03-30 | 2023-03-31 | 株式会社Lg化学 | 有机发光器件 |
WO2018189134A1 (de) * | 2017-04-13 | 2018-10-18 | Merck Patent Gmbh | Zusammensetzung für organische elektronische vorrichtungen |
JP2020520970A (ja) | 2017-05-22 | 2020-07-16 | メルク パテント ゲーエムベーハー | 電子デバイス用六環性ヘテロ芳香族化合物 |
EP3649123B1 (de) * | 2017-07-05 | 2023-03-15 | Merck Patent GmbH | Zusammensetzung für organische elektronische vorrichtungen |
WO2019017730A1 (ko) * | 2017-07-20 | 2019-01-24 | 주식회사 엘지화학 | 신규한 헤테로 고리 화합물 및 이를 이용한 유기 발광 소자 |
KR102132350B1 (ko) * | 2017-07-20 | 2020-07-09 | 주식회사 엘지화학 | 신규한 헤테로 고리 화합물 및 이를 이용한 유기 발광 소자 |
KR101856728B1 (ko) | 2017-08-10 | 2018-05-10 | 주식회사 엘지화학 | 유기 발광 소자 |
US11437588B2 (en) | 2017-10-24 | 2022-09-06 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
KR102072923B1 (ko) * | 2017-11-03 | 2020-02-10 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
WO2019088751A1 (ko) * | 2017-11-03 | 2019-05-09 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
KR102123745B1 (ko) | 2017-11-28 | 2020-06-16 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
KR102181841B1 (ko) | 2017-11-28 | 2020-11-23 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
KR102160860B1 (ko) | 2017-11-28 | 2020-10-06 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
KR102258046B1 (ko) | 2017-12-27 | 2021-05-28 | 삼성에스디아이 주식회사 | 유기 화합물, 조성물, 유기 광전자 소자 및 표시 장치 |
TWI811290B (zh) | 2018-01-25 | 2023-08-11 | 德商麥克專利有限公司 | 用於有機電致發光裝置的材料 |
CN111683940B (zh) * | 2018-05-29 | 2023-09-12 | 株式会社Lg化学 | 杂环化合物及包含其的有机发光器件 |
WO2019229011A1 (de) * | 2018-05-30 | 2019-12-05 | Merck Patent Gmbh | Zusammensetzung für organische elektronische vorrichtungen |
CN112219292A (zh) | 2018-06-07 | 2021-01-12 | 默克专利有限公司 | 有机电致发光器件 |
KR102322698B1 (ko) | 2018-06-22 | 2021-11-09 | 엘티소재주식회사 | 헤테로고리 화합물, 이를 포함하는 유기 발광 소자, 유기 발광 소자의 유기물층용 조성물 및 유기 발광 소자의 제조 방법 |
US11581497B2 (en) | 2018-07-09 | 2023-02-14 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
KR102233654B1 (ko) | 2018-07-23 | 2021-03-30 | 주식회사 엘지화학 | 화합물 및 이를 포함하는 유기 발광 소자 |
US12010912B2 (en) | 2018-07-24 | 2024-06-11 | Lg Chem, Ltd. | Heterocyclic compound and organic light emitting device comprising the same |
TWI826522B (zh) | 2018-09-12 | 2023-12-21 | 德商麥克專利有限公司 | 電致發光裝置 |
TW202030902A (zh) | 2018-09-12 | 2020-08-16 | 德商麥克專利有限公司 | 電致發光裝置 |
KR20210068054A (ko) | 2018-09-27 | 2021-06-08 | 메르크 파텐트 게엠베하 | 유기 전자 디바이스에서 활성 화합물로 사용될 수 있는 화합물 |
WO2020064662A2 (de) | 2018-09-27 | 2020-04-02 | Merck Patent Gmbh | Verfahren zur herstellung von sterisch gehinderten stickstoffhaltigen heteroaromatischen verbindungen |
EP3877369A1 (de) | 2018-11-05 | 2021-09-15 | Merck Patent GmbH | In einer organischen elektronischen vorrichtung einsetzbare verbindungen |
WO2020094542A1 (de) | 2018-11-06 | 2020-05-14 | Merck Patent Gmbh | 5,6-diphenyl-5,6-dihydro-dibenz[c,e][1,2]azaphosphorin- und 6-phenyl-6h-dibenzo[c,e][1,2]thiazin-5,5-dioxid-derivate und ähnliche verbindungen als organische elektrolumineszenzmaterialien für oleds |
US20220006018A1 (en) | 2018-11-14 | 2022-01-06 | Merck Patent Gmbh | Compounds that can be used for producing an organic electronic device |
WO2020099307A1 (de) | 2018-11-15 | 2020-05-22 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
KR102290359B1 (ko) * | 2018-12-11 | 2021-08-19 | 엘티소재주식회사 | 헤테로고리 화합물, 이를 포함하는 유기 발광 소자, 이의 제조 방법 및 유기물층용 조성물 |
TW202039493A (zh) | 2018-12-19 | 2020-11-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置之材料 |
KR102261984B1 (ko) * | 2018-12-28 | 2021-06-09 | 엘티소재주식회사 | 유기 발광 소자, 이의 제조 방법 및 유기물층용 조성물 |
WO2020169241A1 (de) | 2019-02-18 | 2020-08-27 | Merck Patent Gmbh | Zusammensetzung für organische elektronische vorrichtungen |
KR20210137148A (ko) | 2019-03-12 | 2021-11-17 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 재료 |
US20220177478A1 (en) | 2019-03-20 | 2022-06-09 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2020193447A1 (de) | 2019-03-25 | 2020-10-01 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
CN109928945B (zh) * | 2019-04-11 | 2022-11-04 | 西安欧得光电材料有限公司 | 一种1-溴二苯并呋喃及其合成方法 |
WO2020208475A1 (ja) * | 2019-04-12 | 2020-10-15 | 株式会社半導体エネルギー研究所 | 有機化合物、発光デバイス、発光装置、電子機器、および照明装置 |
WO2021015603A1 (ko) * | 2019-07-24 | 2021-01-28 | 주식회사 엘지화학 | 신규한 화합물 및 이를 이용한 유기발광 소자 |
JP2022546334A (ja) | 2019-08-26 | 2022-11-04 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセントデバイスのための材料 |
CN114341117A (zh) | 2019-09-02 | 2022-04-12 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
TW202122558A (zh) | 2019-09-03 | 2021-06-16 | 德商麥克專利有限公司 | 用於有機電致發光裝置之材料 |
CN114401945A (zh) | 2019-09-20 | 2022-04-26 | 默克专利有限公司 | 作为用于电子器件的材料的迫位缩合杂环化合物 |
WO2021078710A1 (en) | 2019-10-22 | 2021-04-29 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2021078831A1 (de) | 2019-10-25 | 2021-04-29 | Merck Patent Gmbh | In einer organischen elektronischen vorrichtung einsetzbare verbindungen |
CN110922391B (zh) * | 2019-10-31 | 2020-11-20 | 陕西莱特光电材料股份有限公司 | 含氮化合物、电子元件及电子装置 |
KR102288205B1 (ko) * | 2019-12-13 | 2021-08-11 | 엘티소재주식회사 | 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
TW202136471A (zh) | 2019-12-17 | 2021-10-01 | 德商麥克專利有限公司 | 有機電致發光裝置用的材料 |
JP2023506572A (ja) | 2019-12-18 | 2023-02-16 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 有機エレクトロルミネッセンス素子のための芳香族化合物 |
KR20220116008A (ko) | 2019-12-19 | 2022-08-19 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 다환 화합물 |
CN115052865A (zh) | 2020-01-29 | 2022-09-13 | 默克专利有限公司 | 苯并咪唑衍生物 |
CN115135741A (zh) | 2020-02-25 | 2022-09-30 | 默克专利有限公司 | 杂环化合物在有机电子器件中的用途 |
CN115244728A (zh) | 2020-03-02 | 2022-10-25 | 默克专利有限公司 | 砜化合物在有机电子器件中的用途 |
EP4118696B1 (de) | 2020-03-11 | 2023-12-20 | Merck Patent GmbH | Organische elektrolumineszierende vorrichtung |
EP4121432A1 (de) | 2020-03-17 | 2023-01-25 | Merck Patent GmbH | Heteroaromatische verbindungen für organische elektrolumineszenzvorrichtungen |
KR20220154751A (ko) | 2020-03-17 | 2022-11-22 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 복소환 화합물 |
WO2021191117A1 (de) | 2020-03-24 | 2021-09-30 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
US20230157171A1 (en) | 2020-03-26 | 2023-05-18 | Merck Patent Gmbh | Cyclic compounds for organic electroluminescent devices |
CN115335382A (zh) | 2020-04-02 | 2022-11-11 | 默克专利有限公司 | 用于有机电致发光器件的材料 |
EP4132939B1 (de) | 2020-04-06 | 2024-01-31 | Merck Patent GmbH | Polycyclische verbindungen für organische elektrolumineszenzvorrichtungen |
WO2022002771A1 (de) | 2020-06-29 | 2022-01-06 | Merck Patent Gmbh | Heterocyclische verbindungen für organische elektrolumineszenzvorrichtungen |
US20230312612A1 (en) | 2020-06-29 | 2023-10-05 | Merck Patent Gmbh | Heteroaromatic compounds for organic electroluminescent devices |
KR20230049107A (ko) | 2020-08-06 | 2023-04-12 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 재료 |
KR20230053629A (ko) | 2020-08-18 | 2023-04-21 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 재료 |
JP2023539825A (ja) | 2020-08-19 | 2023-09-20 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセントデバイスのための材料 |
CN114276360B (zh) * | 2020-09-28 | 2024-09-06 | 江苏绿人半导体有限公司 | 一种有机化合物及有机电致发光器件 |
CN114315845B (zh) * | 2020-09-28 | 2024-09-10 | 江苏绿人半导体有限公司 | 一种有机化合物及在有机电致发光器件中的应用 |
TW202229215A (zh) | 2020-09-30 | 2022-08-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置功能層之結構化的化合物 |
TW202222748A (zh) | 2020-09-30 | 2022-06-16 | 德商麥克專利有限公司 | 用於結構化有機電致發光裝置的功能層之化合物 |
KR20230088748A (ko) | 2020-10-16 | 2023-06-20 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 헤테로원자를 포함하는 화합물 |
KR20230088415A (ko) | 2020-10-16 | 2023-06-19 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 복소환 화합물 |
CN116601157A (zh) | 2020-11-10 | 2023-08-15 | 默克专利有限公司 | 用于有机电致发光器件的含硫化合物 |
US20230416264A1 (en) | 2020-12-02 | 2023-12-28 | Merck Patent Gmbh | Heterocyclic compounds for organic electroluminescent devices |
EP4259628A2 (de) | 2020-12-10 | 2023-10-18 | Merck Patent GmbH | Materialien für organische elektrolumineszenzvorrichtungen |
KR20230122093A (ko) | 2020-12-18 | 2023-08-22 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 질소 함유 화합물 |
US20240101560A1 (en) | 2020-12-18 | 2024-03-28 | Merck Patent Gmbh | Nitrogenous heteroaromatic compounds for organic electroluminescent devices |
TW202241899A (zh) | 2020-12-18 | 2022-11-01 | 德商麥克專利有限公司 | 用於有機電致發光裝置之芳烴化合物 |
US20240083891A1 (en) | 2021-01-05 | 2024-03-14 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
CN116710454A (zh) | 2021-01-25 | 2023-09-05 | 默克专利有限公司 | 用于有机电致发光器件的含氮化合物 |
KR20230154439A (ko) | 2021-03-02 | 2023-11-08 | 메르크 파텐트 게엠베하 | 유기 전계발광 디바이스용 화합물 |
US20240092783A1 (en) | 2021-03-18 | 2024-03-21 | Merck Patent Gmbh | Heteroaromatic compounds for organic electroluminescent devices |
KR20240005782A (ko) | 2021-04-29 | 2024-01-12 | 메르크 파텐트 게엠베하 | 유기 전계 발광 디바이스용 재료 |
KR20240005806A (ko) | 2021-04-29 | 2024-01-12 | 메르크 파텐트 게엠베하 | 유기 전계발광 디바이스용 재료 |
US20240246983A1 (en) | 2021-04-30 | 2024-07-25 | Merck Patent Gmbh | Nitrogenous heterocyclic compounds for organic electroluminescent devices |
KR20240012506A (ko) | 2021-05-21 | 2024-01-29 | 메르크 파텐트 게엠베하 | 적어도 하나의 기능성 물질의 연속 정제 방법 및 적어도 하나의 기능성 물질의 연속 정제를 위한 디바이스 |
DE112022003409A5 (de) | 2021-07-06 | 2024-05-23 | MERCK Patent Gesellschaft mit beschränkter Haftung | Materialien für organische elektrolumineszenzvorrichtungen |
CN117980439A (zh) | 2021-09-14 | 2024-05-03 | 默克专利有限公司 | 用于有机电致发光器件的含硼杂环化合物 |
WO2023052313A1 (de) | 2021-09-28 | 2023-04-06 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
KR20240075872A (ko) | 2021-09-28 | 2024-05-29 | 메르크 파텐트 게엠베하 | 전자 디바이스용 재료 |
WO2023052275A1 (de) | 2021-09-28 | 2023-04-06 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
CN118056486A (zh) | 2021-09-28 | 2024-05-17 | 默克专利有限公司 | 用于电子器件的材料 |
CN118020406A (zh) | 2021-09-30 | 2024-05-10 | 默克专利有限公司 | 有机电致发光器件 |
KR20240091021A (ko) | 2021-10-27 | 2024-06-21 | 메르크 파텐트 게엠베하 | 유기 전계발광 디바이스용 붕소 및 질소 복소환 화합물 |
WO2023094412A1 (de) | 2021-11-25 | 2023-06-01 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2023110742A1 (de) | 2021-12-13 | 2023-06-22 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
CN118354991A (zh) | 2021-12-21 | 2024-07-16 | 默克专利有限公司 | 用于制备氘化的有机化合物的方法 |
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WO2023161167A1 (de) | 2022-02-23 | 2023-08-31 | Merck Patent Gmbh | Stickstoffhaltige heterocyclen für organische elektrolumineszenzvorrichtungen |
CN118647622A (zh) | 2022-02-23 | 2024-09-13 | 默克专利有限公司 | 用于有机电致发光器件的芳族杂环 |
WO2023213837A1 (de) | 2022-05-06 | 2023-11-09 | Merck Patent Gmbh | Cyclische verbindungen für organische elektrolumineszenzvorrichtungen |
WO2023222559A1 (de) | 2022-05-18 | 2023-11-23 | Merck Patent Gmbh | Verfahren zur herstellung von deuterierten organischen verbindungen |
WO2023247338A1 (de) | 2022-06-20 | 2023-12-28 | Merck Patent Gmbh | Organische heterocyclen für photoelektrische vorrichtungen |
WO2023247345A1 (de) | 2022-06-20 | 2023-12-28 | Merck Patent Gmbh | Heterocyclen für photoelektrische vorrichtungen |
WO2024013004A1 (de) | 2022-07-11 | 2024-01-18 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
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WO2024061942A1 (de) | 2022-09-22 | 2024-03-28 | Merck Patent Gmbh | Stickstoffenthaltende verbindungen für organische elektrolumineszenzvorrichtungen |
WO2024094592A2 (de) | 2022-11-01 | 2024-05-10 | Merck Patent Gmbh | Stickstoffhaltige heterocyclen für organische elektrolumineszenzvorrichtungen |
WO2024121133A1 (de) | 2022-12-08 | 2024-06-13 | Merck Patent Gmbh | Organische elektronische vorrichtung und spezielle materialien für organische elektronische vorrichtungen |
WO2024132993A1 (de) | 2022-12-19 | 2024-06-27 | Merck Patent Gmbh | Materialien für elektronische vorrichtungen |
WO2024133048A1 (en) | 2022-12-20 | 2024-06-27 | Merck Patent Gmbh | Method for preparing deuterated aromatic compounds |
WO2024149694A1 (de) | 2023-01-10 | 2024-07-18 | Merck Patent Gmbh | Stickstoffhaltige heterocyclen für organische elektrolumineszenzvorrichtungen |
WO2024153568A1 (de) | 2023-01-17 | 2024-07-25 | Merck Patent Gmbh | Heterocyclen für organische elektrolumineszenzvorrichtungen |
WO2024184050A1 (de) | 2023-03-07 | 2024-09-12 | Merck Patent Gmbh | Cyclische stickstoffverbindungen für organische elektrolumineszenzvorrichtungen |
CN117624146B (zh) * | 2024-01-24 | 2024-04-30 | 吉林奥来德光电材料股份有限公司 | 一种磷光主体材料及其制备方法和有机电致发光器件 |
Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP4496949B2 (ja) * | 2004-12-13 | 2010-07-07 | 株式会社豊田自動織機 | 有機el素子 |
JP5194596B2 (ja) * | 2007-07-11 | 2013-05-08 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
JP5604848B2 (ja) | 2009-10-19 | 2014-10-15 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、照明装置及び表示装置 |
CN102201541B (zh) * | 2010-03-23 | 2015-11-25 | 株式会社半导体能源研究所 | 发光元件、发光装置、电子设备及照明装置 |
US9257651B2 (en) | 2010-06-18 | 2016-02-09 | Konica Minolta Holdings, Inc. | Organic electroluminescence element and method for manufacturing organic electroluminescence element |
JP6007467B2 (ja) | 2010-07-27 | 2016-10-12 | コニカミノルタ株式会社 | 有機エレクトロルミネッセンス素子材料、有機エレクトロルミネッセンス素子、 |
KR20120109744A (ko) | 2011-03-25 | 2012-10-09 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전자재료용 화합물 및 이를 포함하는 유기 전계 발광 소자 |
JP5831068B2 (ja) | 2011-09-13 | 2015-12-09 | コニカミノルタ株式会社 | 縮合複素環化合物の製造方法 |
BR112014006697A2 (pt) * | 2011-09-21 | 2017-03-28 | Merck Patent Gmbh | derivados de carbazol para dispositivos eletroluminescentes orgânicos |
WO2013081315A1 (ko) * | 2011-11-28 | 2013-06-06 | 덕산하이메탈(주) | 유기전기소자용 화합물, 이를 포함하는 유기전기소자 및 그 전자 장치 |
KR101497124B1 (ko) | 2011-11-28 | 2015-03-06 | 덕산네오룩스 주식회사 | 유기전기소자용 화합물, 이를 포함하는 유기전기소자 및 그 전자 장치 |
WO2013102992A1 (ja) * | 2012-01-05 | 2013-07-11 | 出光興産株式会社 | 有機エレクトロルミネッセンス素子用材料とそれを用いた素子 |
JP6169078B2 (ja) | 2012-07-19 | 2017-07-26 | 新日鉄住金化学株式会社 | 有機電界発光素子 |
KR20140035737A (ko) | 2012-09-14 | 2014-03-24 | 롬엔드하스전자재료코리아유한회사 | 신규한 유기 전계 발광 화합물 및 이를 포함하는 유기 전계 발광 소자 |
US9209411B2 (en) * | 2012-12-07 | 2015-12-08 | Universal Display Corporation | Organic electroluminescent materials and devices |
TWI652014B (zh) * | 2013-09-13 | 2019-03-01 | 美商艾佛艾姆希公司 | 雜環取代之雙環唑殺蟲劑 |
AU2015208247B2 (en) * | 2014-01-21 | 2021-05-27 | Universiteit Gent | Muscle-specific nucleic acid regulatory elements and methods and use thereof |
WO2015169412A1 (de) | 2014-05-05 | 2015-11-12 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
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- 2015-07-03 EP EP15734298.1A patent/EP3174954B1/de active Active
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Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI637952B (zh) * | 2016-06-29 | 2018-10-11 | 三星Sdi股份有限公司 | 用於有機光電裝置的化合物、用於有機光電裝置的組成物以及有機光電裝置及顯示裝置 |
US11678572B2 (en) | 2016-06-29 | 2023-06-13 | Samsung Sdi Co., Ltd. | Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device and display apparatus |
US11706975B2 (en) | 2016-06-29 | 2023-07-18 | Samsung Sdi Co., Ltd. | Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device and display apparatus |
US11084806B2 (en) | 2016-07-12 | 2021-08-10 | Samsung Sdi Co., Ltd. | Compound for organic optoelectronic device, composition for organic optoelectronic device, organic optoelectronic device, and display device |
US11264574B2 (en) | 2016-07-29 | 2022-03-01 | Samsung Sdi Co., Ltd. | Composition for organic optoelectronic element, organic optoelectronic element, and display device |
TWI641606B (zh) * | 2016-11-07 | 2018-11-21 | 南韓商Lg化學股份有限公司 | 化合物以及包含此化合物的有機發光裝置 |
US11208402B2 (en) | 2016-11-07 | 2021-12-28 | Lg Chem, Ltd. | Heterocyclic compound and organic light emitting device comprising the same |
US11802123B2 (en) | 2016-11-07 | 2023-10-31 | Lg Chem, Ltd. | Heterocyclic compound and organic light emitting device comprising the same |
US11158817B2 (en) | 2017-01-05 | 2021-10-26 | Samsung Sdi Co., Ltd. | Compound for organic optoelectronic device, composition for organic optoelectronic device and organic optoelectronic device and display device |
US11296281B2 (en) | 2017-03-15 | 2022-04-05 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
TWI780126B (zh) * | 2017-03-15 | 2022-10-11 | 德商麥克專利有限公司 | 有機電致發光裝置之材料、彼之製法及彼之用途 |
CN110621668A (zh) * | 2017-03-24 | 2019-12-27 | 喜星素材株式会社 | 杂环化合物与包含其的有机发光装置 |
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EP3174954A1 (de) | 2017-06-07 |
US11309497B2 (en) | 2022-04-19 |
TWI671293B (zh) | 2019-09-11 |
KR20170039209A (ko) | 2017-04-10 |
JP2020090495A (ja) | 2020-06-11 |
WO2016015810A1 (de) | 2016-02-04 |
KR102474330B1 (ko) | 2022-12-05 |
JP2017524707A (ja) | 2017-08-31 |
US20220165961A1 (en) | 2022-05-26 |
US20170207399A1 (en) | 2017-07-20 |
CN106661006B (zh) | 2019-11-08 |
EP3174954B1 (de) | 2019-02-13 |
CN106661006A (zh) | 2017-05-10 |
JP6891109B2 (ja) | 2021-06-18 |
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