CN101679851B - 磷杂菲化合物及使用该磷杂菲化合物的有机发光二极管 - Google Patents
磷杂菲化合物及使用该磷杂菲化合物的有机发光二极管 Download PDFInfo
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- CN101679851B CN101679851B CN2008800148872A CN200880014887A CN101679851B CN 101679851 B CN101679851 B CN 101679851B CN 2008800148872 A CN2008800148872 A CN 2008800148872A CN 200880014887 A CN200880014887 A CN 200880014887A CN 101679851 B CN101679851 B CN 101679851B
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- LJUXFZKADKLISH-UHFFFAOYSA-N benzo[f]phosphinoline Chemical class C1=CC=C2C3=CC=CC=C3C=CC2=P1 LJUXFZKADKLISH-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 109
- 125000003118 aryl group Chemical group 0.000 claims description 66
- 125000005842 heteroatom Chemical group 0.000 claims description 59
- -1 phospho hetero phenanthrene compound Chemical class 0.000 claims description 46
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 150000002367 halogens Chemical class 0.000 claims description 28
- 229910052760 oxygen Inorganic materials 0.000 claims description 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- 239000001301 oxygen Substances 0.000 claims description 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 16
- 125000005104 aryl silyl group Chemical group 0.000 claims description 15
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
- 239000005864 Sulphur Substances 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 125000001769 aryl amino group Chemical group 0.000 claims description 9
- 125000004450 alkenylene group Chemical group 0.000 claims description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910005965 SO 2 Inorganic materials 0.000 claims description 5
- 150000001336 alkenes Chemical class 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 3
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- LJDZFAPLPVPTBD-UHFFFAOYSA-N nitroformic acid Chemical compound OC(=O)[N+]([O-])=O LJDZFAPLPVPTBD-UHFFFAOYSA-N 0.000 claims description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000005865 C2-C10alkynyl group Chemical group 0.000 claims 1
- 125000003968 arylidene group Chemical group [H]C(c)=* 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 239000004065 semiconductor Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 239000010410 layer Substances 0.000 description 30
- 239000010408 film Substances 0.000 description 29
- 239000000463 material Substances 0.000 description 29
- 125000000217 alkyl group Chemical group 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 229920002554 vinyl polymer Polymers 0.000 description 20
- 238000005160 1H NMR spectroscopy Methods 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 15
- 230000002194 synthesizing effect Effects 0.000 description 13
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 12
- 239000012300 argon atmosphere Substances 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000005424 photoluminescence Methods 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 238000001816 cooling Methods 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 238000000151 deposition Methods 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 8
- 229910052698 phosphorus Inorganic materials 0.000 description 8
- 238000001556 precipitation Methods 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 description 7
- 150000004646 arylidenes Chemical group 0.000 description 7
- 230000008021 deposition Effects 0.000 description 7
- 239000011574 phosphorus Substances 0.000 description 7
- 238000001228 spectrum Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000009834 vaporization Methods 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 235000015320 potassium carbonate Nutrition 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 3
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000001118 alkylidene group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 239000004411 aluminium Substances 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- OMFXVFTZEKFJBZ-HJTSIMOOSA-N corticosterone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OMFXVFTZEKFJBZ-HJTSIMOOSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 3
- 150000003839 salts Chemical group 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- XSUNFLLNZQIJJG-UHFFFAOYSA-N 2-n-naphthalen-2-yl-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N(C=1C=CC=CC=1)C=1C=C2C=CC=CC2=CC=1)C1=CC=CC=C1 XSUNFLLNZQIJJG-UHFFFAOYSA-N 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- 0 CC(*)c(cc1)ccc1-c1nnc(*=C)[o]1 Chemical compound CC(*)c(cc1)ccc1-c1nnc(*=C)[o]1 0.000 description 2
- DXHXKMIMSJAQAH-NTCAYCPXSA-N COc(c(/C=C/c(cc1)ccc1F)c1)cc(P2(Oc(ccc(-c3ccccc3)c3)c3-c3c2cccc3)=O)c1OC Chemical compound COc(c(/C=C/c(cc1)ccc1F)c1)cc(P2(Oc(ccc(-c3ccccc3)c3)c3-c3c2cccc3)=O)c1OC DXHXKMIMSJAQAH-NTCAYCPXSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical class O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000011162 core material Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- BDMBWENRFFKJON-JWQCQUIFSA-N n-[(2r,4r)-1,4-dihydroxy-4-phenylbutan-2-yl]hexadecanamide Chemical compound CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)C[C@@H](O)C1=CC=CC=C1 BDMBWENRFFKJON-JWQCQUIFSA-N 0.000 description 2
- GIFAOSNIDJTPNL-UHFFFAOYSA-N n-phenyl-n-(2-phenylphenyl)naphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=CC=C1C1=CC=CC=C1 GIFAOSNIDJTPNL-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 238000000059 patterning Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 150000004714 phosphonium salts Chemical class 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 2
- 125000006654 (C3-C12) heteroaryl group Chemical group 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- AIDLAEPHWROGFI-UHFFFAOYSA-N 2-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=C(C(O)=O)C=CC=C1C(O)=O AIDLAEPHWROGFI-UHFFFAOYSA-N 0.000 description 1
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 1
- WZWIQYMTQZCSKI-UHFFFAOYSA-N 4-cyanobenzaldehyde Chemical compound O=CC1=CC=C(C#N)C=C1 WZWIQYMTQZCSKI-UHFFFAOYSA-N 0.000 description 1
- UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 1
- PNWSHHILERSSLF-UHFFFAOYSA-N 4-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=CC=C(C(O)=O)C=C1C(O)=O PNWSHHILERSSLF-UHFFFAOYSA-N 0.000 description 1
- MCMWRWKXPXXZAS-UHFFFAOYSA-N 6-chloro-3-[3-(4-chloro-3,5-dimethylphenoxy)propyl]-1h-indole-2-carboxylic acid Chemical compound CC1=C(Cl)C(C)=CC(OCCCC=2C3=CC=C(Cl)C=C3NC=2C(O)=O)=C1 MCMWRWKXPXXZAS-UHFFFAOYSA-N 0.000 description 1
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- IGUDRSXXGZKSLT-PSLBBUNJSA-N CC(/C(/N)=C(\N)/Oc(cc(c(O/C(/N)=C(\C)/N)c1)[O]2Oc(cccc3)c3-c3c2cccc3)c1-c1c(cccc2)c2ccc1)=C Chemical compound CC(/C(/N)=C(\N)/Oc(cc(c(O/C(/N)=C(\C)/N)c1)[O]2Oc(cccc3)c3-c3c2cccc3)c1-c1c(cccc2)c2ccc1)=C IGUDRSXXGZKSLT-PSLBBUNJSA-N 0.000 description 1
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Abstract
本发明涉及具有优异发光性的新型磷杂菲化合物和使用该磷杂菲化合物的有机发光二极管(OLED)。
Description
技术领域
本发明涉及作为具有发光性的磷化合物的磷杂菲化合物和使用该磷杂菲化合物的具有优异的发光性的有机发光二极管(下文称作OLED)。
背景技术
作为自发光显示器的OLED具有宽视角、快响应速度和低电压驱动等几大优点,目前已被用作下一代平板显示器。
普通的OLED基本由以有机化合物制成的多层薄膜结构构成,所述多层薄膜结构例如有位于OLED的阴极和阳极之间的空穴输送层、发光层、电子输送层和空穴输送层等。OLED利用以下原理:在两个电极之间施加电流时,通过由阴极注入电子和由阳极注入空穴而在发光层重组电子与空穴,并在能级由激发态下降至基态的过程中发光。
自从Eastman Kodak Co.(USA)于1987年率先开发出的使用芳香二胺和Alq3作为形成发光层的材料的OLED(Appl.Phys.Lett.p913,(1987))为世人所知以来,旨在改进萘基二胺类发光材料(美国专利第6549345号公报)、荧光型发光材料(美国专利第6803121号公报)(例如蒽类材料)和磷型发光材料(例如具有更高效率的使用铱络合物的发光材料)(美国专利第6858327号公报)的性能的研究一直都在进行之中。如今,OLED已被实际应用于手机等小型平板显示器上。
作为到目前为止所知的发蓝光化合物,有由Idemitsu Kosan(EP 388,768(1990),日本九州大学(PRO,SRIE,1910,180(1993))开发的联苯二烯(distryl)类蒽衍生物等。然而,发蓝光材料的发光效率低于其它颜色的发光体,因而应该进一步改进薄膜稳定性和耐热性等。
此外,常见的是,使用基质材料作为磷型发光材料以通过能量传递使效率最大化。例如,作为低分子磷基质,有4,4’-N,N’-二咔唑-联苯(CBP)、1,3-二(9-咔唑基)苯(mCP)等(Journal of Materials chemistry(2003)13,2157-2163;Journal of Materials chemistry(2005)15,2304-2315);作为聚合磷基质,有聚(N-乙烯基咔唑)(PVK)等。近来,C.W.Tang的团队报道了具有单层结构和多层结构的有机发光二极管使用聚合的聚乙烯基咔唑作为磷基质,而不是使用CBP和mCP作为磷基质(J.Appl.Phys.,Vol.92,No.7,3447)。然而,该有机发光二极管具有以下缺点,即,在被长时间驱动时会因生成的驱动热而使器件劣化。具体而言,由于mCP等材料具有低玻璃化转变温度Tg,因而在器件被驱动时容易结晶为薄膜材料,由此产生因驱动热引起色纯度变化和器件寿命缩短的重大缺陷。因此,在长时间和高效率的OLED的材料开发中,除了将色纯度和效率考虑为重要变量之外,也将耐热性考虑为重要变量。
通过引入其为磷化合物的磷杂菲衍生物作为OLED用材料,本发明人经过不懈努力,已经开发出具有优异的发光性和耐热性的材料,并且已经成功地使用所述材料进行了OLED构造。
磷杂菲衍生物过去仅用作阻燃剂等(韩国专利第1993-3867号公报),但极少有用作OLED用材料的实例。在相关技术的美国专利公开第2002-0193522号中,已知包含磷杂菲化合物的高分子材料被用作OLED用材料。作为包含在高分子材料中的磷杂菲化合物,已知以下三种化合物。然而,已知技术限于以下三种化合物,并且不适用于EL(电致发光)。
发明内容
技术问题
本发明的一个目的在于提供具有耐热性和优异的发光性的磷杂菲化合物,所述耐热性和优异的发光性是实现如上所述的高效率和长使用寿命的器件所必需的。本发明的另一目的在于提供含有制备的磷杂菲化合物作为发光材料的有机发光二极管。
技术方案
本发明涉及用作OLED用核心材料的由以下化学式1表示的具有优异的耐热性和发光性的磷杂菲化合物,和包含所述磷杂菲化合物作为发光材料的有机发光二极管。
[化学式1]
在化学式1中,L1是化学键或(C2-C10)亚烯基、(C6-C30)亚芳基或NR11,并且L1的亚烯基或亚芳基可以进一步被选自下述基团的至少一种取代:(C1-C22)烷基、(C6-C30)芳基、(C2-C30)杂芳基、(C6-C30)芳基(C1-C22)烷基、(C1-C22)烷基(C6-C30)芳基、卤素、(C1-C10)烷基甲硅烷基、(C6-C30)芳基甲硅烷基、羧酸、氰基或OR31;
L2是(C2-C10)亚烯基、(C2-C10)亚炔基、(C6-C30)亚芳基、(C2-C30)杂亚芳基或-Ar1-A-Ar2-,并且L2的亚烯基、亚芳基或杂亚芳基可以进一步被选自下述基团的至少一种取代:(C1-C22)烷基、卤素、氰基、羧酸、(C1-C10)烷基甲硅烷基、(C6-C30)芳基甲硅烷基、(C6-C30)芳基、(C2-C30)杂芳基、(C6-C30)芳基(C1-C22)烷基、(C1-C22)烷基(C6-C30)芳基或OR31;
Ar1和Ar2彼此独立且为(C6-C30)亚芳基或(C2-C30)杂亚芳基,并且Ar1和Ar2的亚芳基或杂亚芳基不被取代或进一步被选自下述基团的至少一种取代:(C1-C22)烷基、(C6-C30)芳基、(C6-C30)芳氧基、(C2-C30)杂芳基、卤素、(C1-C10)烷基甲硅烷基、(C6-C30)芳基甲硅烷基、(C1-C22)烷氧基、羧酸或氰基;
A是NR12、(O=)PR13、SiR14R15、SO2或O;
R1是氢、(C1-C22)烷基、(C6-C30)芳基、(C2-C30)杂芳基、卤素、氰基、(C1-C22)烷氧基、(C6-C30)芳氧基、(C6-C30)芳磺酰基、单或二(C1-C10)烷基氨基、单或二(C6-C30)芳基氨基、(C2-C7)烯氧基、(C2-C7)炔氧基、(C2-C7)烯羰氧基、(C2-C7)炔羰氧基、(C1-C10)烷基甲硅烷基、(C6-C30)芳基甲硅烷基或
,并且R1的烷基、芳基、杂芳基、烷氧基、芳氧基、芳磺酰基、烷基氨基、芳基氨基、烯氧基、炔氧基、烷基甲硅烷基或芳基甲硅烷基可以进一步被选自下述基团的至少一种取代:(C1-C10)烷基、卤素、氰基、硝基、羧酸、(C6-C30)芳基、单或二(C1-C10)烷基氨基、单或二(C6-C30)芳基氨基、(C1-C10)烷基甲硅烷基或(C6-C30)芳基甲硅烷基;
L11是化学键或(C2-C10)亚烯基、(C6-C30)亚芳基或NR16,并且L11的亚烯基或亚芳基可以进一步被选自下述基团的至少一种取代:(C1-C22)烷基、(C1-C22)烷氧基、(C3-C22)环烷基、(C6-C30)芳基、氰基、卤素、氨基、单或二(C1-C10)烷基氨基、单或二(C6-C30)芳基氨基、硝基或羟基;
R2~R9彼此独立且为氢、(C1-C22)烷基、包含氧、氮或硫的(C1-C22)烷基、(C1-C22)烷氧基、(C3-C22)环烷基、(C3-C22)环烷基(C1-C22)烷基、(C6-C30)芳基、卤素、氰基、氨基、单或二(C1-C10)烷基氨基、单或二(C6-C30)芳基氨基、羟基、硝基、单或二苄基氨基或(C3-C10)环烷基氨基,并且R2~R9通过(C3-C5)亚烷基或(C3-C5)亚烯基与相邻取代基的碳结合以形成稠环,稠环的碳可以被替换为选自氧、硫或氮的杂原子,并且R2~R9的烷基、烷氧基、环烷基、环烷基烷基、芳基或氨基可以进一步被选自下述基团的至少一种取代:(C1-C10)烷基、卤素、(C6-C30)芳基、(C1-C10)烷基甲硅烷基或(C6-C30)芳基甲硅烷基;
R11~R16彼此独立且为(C1-C22)烷基、(C3-C22)环烷基、(C6-C30)芳基、单或二(C1-C10)烷基氨基、单或二(C6-C30)芳基氨基或氨基,并且R11~R16的烷基、环烷基或芳基可以进一步被选自下述基团的至少一种取代:卤素、(C1-C22)烷基、(C6-C30)芳基、(C1-C22)烷氧基、包含氧、氮或硫的至少一种的3元至7元杂环烷基,或氰基;
R21~R28彼此独立且为氢、(C1-C22)烷基、包含氧、氮或硫的(C1-C22)烷基、(C1-C22)烷氧基、(C3-C22)环烷基、(C3-C22)环烷基(C1-C22)烷基、(C6-C30)芳基、卤素、氰基、氨基、单或二(C1-C10)烷基氨基、单或二(C6-C30)芳基氨基、羟基、硝基、单或二苄基氨基或(C3-C10)环烷基氨基,并且R21~R28通过(C3-C5)亚烷基或(C3-C5)亚烯基与相邻取代基的碳结合以形成稠环,稠环的碳可以被替换为选自氧、硫或氮的杂原子,并且R21~R28的烷基、烷氧基、环烷基、环烷基烷基、芳基或氨基可以进一步被选自下述基团的至少一种取代:(C1-C10)烷基、卤素、(C6-C30)芳基、(C1-C10)烷基甲硅烷基或(C6-C30)芳基甲硅烷基;并且
R31是(C1-C22)烷基、(C6-C30)芳基、(C2-C10)烯基或(C1-C22)烷羰基,并且R31的烷基、芳基或烷羰基可以进一步被选自下述基团的至少一种取代:包含N、O和S的至少一种的3元至5元杂环烷基、(C3-C22)环烷基、(C2-C10)炔基、(C2-C10)烯基、氰基或卤素。
(C6-C30)芳基优选为(C6-C18)芳基,更优选为(C6-C12)芳基。芳基的具体实例可以包括诸如苯基、萘基、联苯基、四氢萘基、茚满基、芴基、菲基、蒽基、三亚苯基(triphenylenyl)、芘基、crycenyl和萘并萘基等芳香基。
(C2-C30)杂芳基优选为(C3-C18)杂芳基,更优选为(C3-C12)杂芳基。杂芳基可以包含选自N、O、P或S的1~3个杂原子作为芳环结构原子,其中其它芳环结构原子是指芳基的碳。杂芳基包括例如通过氧化或季盐化环中的杂原子而形成N-氧化物或季盐的二价芳基。代表性的实例可以包括呋喃基、吡喃基、异苯并呋喃基、吡咯基、咪唑基、吡唑基、异噻唑基、异噁唑基、四唑基、吡啶基、吡嗪基、嘧啶基、哒嗪基、氮茚基、异吲哚基、吲哚基、吲唑基、喹嗪基、异喹啉基、喹啉基、咔唑基、菲啶基和与它们相应的N-氧化物(例如,吡啶基N-氧化物、喹啉基N-氧化物),和它们的季盐等,但不限于这些实例。
B是化学键或NR71、(O=)PR71、SiR73R74、SO2或O;
D是CR81R82、NR83、O、S或SO2;
R31是(C1-C22)烷基、(C6-C30)芳基、(C2-C10)烯基或(C1-C22)烷羰基,并且R31的烷基、烯基或烷羰基可以进一步被选自下述基团的至少一种取代:包含N、O和S的至少一种的3元至5元杂环烷基、(C3-C22)环烷基、(C2-C10)炔基、(C2-C10)烯基、氰基或卤素;
R41~R64彼此独立且为氢、(C1-C22)烷基、(C6-C30)芳基、卤素、(C2-C30)杂芳基、氰基、羧酸、(C1-C10)烷基甲硅烷基、(C6-C30)芳基甲硅烷基、(C6-C30)芳基(C1-C22)烷基、(C1-C22)烷基(C6-C30)芳基或OR31,或者R45和R46或R47和R48与(C3-C5)亚烷基或(C3-C5)亚烯基偶联以形成稠环,并且稠环的碳可以被替换为选自氧、硫或氮的杂原子;
R71~R74彼此独立且为(C1-C22)烷基、(C3-C22)环烷基、(C6-C30)芳基、单或二(C1-C10)烷基氨基、单或二(C6-C30)芳基氨基或氨基,并且R71~R74的烷基、环烷基或芳基可以进一步被选自下述基团的至少一种取代:卤素、(C1-C22)烷基、(C6-C30)芳基、(C1-C22)烷氧基、包含氧、氮或硫的至少一种的3元至7元杂环烷基,或氰基;
R81~R83彼此独立且为氢、(C1-C22)烷基、(C6-C30)芳基、卤素、(C2-C30)杂芳基、氰基、羧酸、(C1-C10)烷基甲硅烷基、(C6-C30)芳基甲硅烷基、(C6-C30)芳基(C1-C22)烷基、(C1-C22)烷基(C6-C30)芳基或(C1-C22)烷氧基;并且
m和n彼此独立且为1~4的整数。
具体而言,选自以下化学结构:
本发明的磷杂菲化合物可以由以下化合物说明,但是本发明不限于以下化合物。
有利效果
本发明还提供了有机EL二极管,其中,电子输送层、发光层和发光/电子输送层包含由化学式1表示的磷杂菲化合物。由化学式1表示的磷杂菲化合物可用作电子输送材料或发光材料。特别是,本发明的磷杂菲化合物可用作电子输送材料。因此,电子输送层或发光层包含本发明的磷杂菲化合物的OELD可在低电能下被驱动,并且即使被长时间驱动时亦能保持发光效率,这使得可实现OLED的长使用寿命。
此外,在制备本发明的由化学式1表示的磷杂菲化合物时,可以使用包括此处所述的方法在内的任何已知方法,只要最终材料的结构相同即可。换言之,用于制备本发明的由化学式1表示的磷杂菲化合物的溶剂、反应温度、浓度或催化剂等不受特别限制,并与制备收率无关。例如,下面将详细描述反应式1。
在反应式1的情况中,通过磷杂菲衍生物与醌的加成反应可以合成酚形式的衍生物。为将合成的衍生物制为卤代甲基,对羟基进行烷氧基化。卤代甲基与三苯基膦反应,使得其被合成为能够进行维蒂希(Wittig)反应的前体。在使用四氢呋喃等有机溶剂的情况下,用于维蒂希反应的单体(通常为鏻盐和苯甲醛衍生物)与诸如钠或烷基锂等强碱催化剂反应。
[反应式1]
附图说明
通过结合附图提供的优选实施方式的下述描述,本发明的上述及其它目的、特征和优点将变得显而易见,附图中:
图1是第一实施方式制备的化合物101的1H-NMR谱;
图2是应用了第一实施方式所制备的化合物101的OLED的紫外吸收(UV-vis)和光致发光(PL)谱;
图3是应用了第八实施方式所制备的化合物108的OLED的紫外吸收(UV-vis)和光致发光(PL)谱;
图4是应用了第九实施方式所制备的化合物109的OLED的紫外吸收(UV-vis)和光致发光(PL)谱;
图5是应用了第一实施方式所制备的化合物101的OLED的电致发光(EL)谱;
图6是应用了第八实施方式所制备的化合物108的OLED的电致发光(EL)谱;和
图7是应用了第九实施方式所制备的化合物109的OLED的电致发光(EL)谱。
具体实施方式
下面将参考本发明的实施方式,描述制备本发明的新型磷杂菲化合物的方法。然而,提供以下实施方式的目的在于帮助理解本发明,因此,本发明的范围不限于这些实施方式。
[第一实施方式]10-{4’-[2-(4-氟苯基)-乙烯基]-2’,5’-二甲氧基苯基}-9-氧杂-10-磷杂菲-10-氧化物(化合物101)的合成
10-(4’-甲基-2’,5’-二羟基苯基)-9,10-二氢-9-氧杂-10-磷杂菲-10-氧化
物(化合物A)的合成
将200g(0.93mol)9,10-二羟基-9-氧杂-10-磷杂菲-10-氧化物、107g(0.88mol)甲基-1,4-苯醌和300ml 2-丁氧基乙醇放入氩气氛围下的1000ml的单口圆底烧瓶中,然后加热回流12小时。反应完成后,将其于常温缓缓冷却以产生沉淀。使用甲醇在减压下过滤沉淀从而获得目标化合物,即,254g(收率:81%)作为白色固体的10-(4’-甲基-2’,5’-二羟基苯基)-9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物(化合物A)。
1H NMR(CDCl3),δ=2.15(s,3H,CH3),6.24(d,1H,芳基),6.75(d,1H,芳基),7.08~7.96(m,8H,芳基)
10-(4’-甲基-2’,5’-二甲氧基苯基)-9,10-二氢-9-氧杂-10-磷杂菲-10-氧
化物(化合物B)的合成
在将20g(0.06mol)10-(4’-甲基-2’,5’-二羟基苯基)-9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物(化合物A)和200ml甲醇放入氩气氛围下的500ml单口圆底烧瓶中并于其中搅拌时,依次向该烧瓶中加入7g(0.13mol)甲醇钠和83g(0.59mol)碘甲烷。然后,将它们加热回流4小时。反应完成后,进一步向其中加入100ml甲醇,并用200ml的乙酸乙酯萃取三次。使用蒸馏水洗涤经萃取的滤液两次,并用无水硫酸镁对其进行干燥,然后在减压下过滤,从而获得目标化合物,即,12.6g(收率:58%)作为白色固体的10-(4’-甲基-2’,5’-二甲氧基苯基)-9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物(化合物B)。
1H NMR(CDCl3),δ=2.17(s,3H,CH3),3.14(s,3H,OCH3),3.81(s,3H,OCH3),6.56(d,1H,芳基),7.03~7.94(m,9H,芳基)
10-(4’-溴甲基-2’,5’-二甲氧基苯基)-9,10-二氢-9-氧杂-10-磷杂菲-10-
氧化物(化合物C)的合成
在将1g(27mmol)10-(4’-甲基-2’,5’-二甲氧基苯基)-9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物(化合物B)和200ml四氯甲烷放入氩气氛围下的100ml单口圆底烧瓶中并于其中搅拌时,依次向该烧瓶中加入0.02g(1.08mmol)AIBN和0.97g(54mmol)N-溴代琥珀酰亚胺。然后,将它们加热回流12小时。反应完成后,向其中进一步加入80ml二氯甲烷,使用蒸馏水洗涤两次,并用无水硫酸镁对其进行干燥,然后在减压下过滤,从而获得1.23g棕色固体。使用展开液(乙酸乙酯/正己烷:1/2)通过快速色谱法将副产物分离出来,从而获得目标化合物,即,0.42g(收率:33%)作为白色固体的10-(4’-溴甲基-2’,5’-二甲氧基苯基)-9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物(化合物C)。
1H NMR(CDCl3),δ=3.14(s,3H,OCH3),3.86(s,3H,OCH3),4.41(s,3H,CH2Br),6.72(d,1H,芳基),7.08~7.95(m,9H,芳基)
10-(4’-三苯基溴化膦-2’,5’-二甲氧基苯基)-9,10-二氢-9-氧杂-10-磷杂
菲-10-氧化物(化合物D)的合成
将14.85g(0.03mol)10-(4’-溴甲基-2’,5’-二甲氧基苯基)-9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物(化合物C)和100mg乙醇放入500ml单口圆底烧瓶中并于其中搅拌,然后向该烧瓶中加入10.26g(0.04mol)三苯基膦。然后,将它们加热回流4小时。反应完成后,将其于常温缓缓冷却。使用乙醚过滤冷却后产生的沉淀从而获得目标化合物,即,23.31g(收率:99%)作为白色固体的10-(4’-三苯基溴化膦-2’,5’-二甲氧基苯基)-9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物(化合物D)。
1H NMR(CDCl3),δ=3.14(s,3H,OCH3),3.26(s,3H,OCH3),5.15(t,1H,CH2P),5.67(t,1H,CH2P),7.16~8.00(m,15H,芳基)
10-{4’-[2-(4-氟苯基)-乙烯基]-2’,5’-二甲氧基苯基}-9-氧杂-10-磷杂菲
-10-氧化物(化合物101)的合成
在将5g(69.6mmol)10-(4’-三苯基溴化膦-2’,5’-二甲氧基苯基)-9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物(化合物D)、0.95g(76.6mmol)4-氟苯甲醛和50ml无水四氢呋喃放入氩气氛围下的100ml单口圆底烧瓶中并于其中搅拌后,向其中缓缓滴入3.3ml(21%的乙醇溶液,83.5mml)21%的乙醇钠。于常温将它们搅拌2小时。反应完成后,将其在减压下蒸发。利用展开液(乙酸乙酯/正己烷:1/1)由该混合物获得目标化合物,即,2.92g(收率:89%)作为白色固体的10-{4’-[2-(4-氟苯基)-乙烯基]-2’,5’-二甲氧基苯基}-9-氧杂-10-磷杂菲-10-氧化物(化合物101)。
1H NMR(CDCl3),δ=2.83(s,3H,OCH3),3.80(s,3H,OCH3),6.51~7.96(m,16H,乙烯基和芳基)
[第二实施方式]10-{4’-[2-(萘)-乙烯基]-2’,5’-二甲氧基苯基}-9-氧杂-10-磷杂菲-10-氧化物(化合物102)的合成
在将1g(69.6mmol)10-(4’-三苯基溴化膦-2’,5’-二甲氧基苯基)-9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物(化合物D)、0.21g(13.9mmol)1-萘甲醛和50ml无水四氢呋喃放入氩气氛围下的100ml单口圆底烧瓶中并于其中搅拌后,向其中缓缓滴入3.3ml(21%的乙醇溶液,83.5mml)21%的乙醇钠。于常温将它们搅拌2小时。反应完成后,将其在减压下蒸发。利用展开液(乙酸乙酯/正己烷:1/1)由该混合物获得目标化合物,即,0.39g(收率:56%)作为白色固体的10-{4’-[2-(萘)-乙烯基]-2’,5’-二甲氧基苯基}-9-氧杂-10-磷杂菲-10-氧化物(化合物102)。
1H NMR(CDCl3),δ=2.83(s,3H,OCH3),3.80(s,3H,OCH3),6.51~7.96(m,19H,乙烯基和芳基)
[第三实施方式]10-{4’-[2-(氰基苯基)-乙烯基]-2’,5’-二甲氧基苯基}-9-氧杂-10-磷杂菲-10-氧化物(化合物103)的合成
在将1g(14mmol)10-(4’-三苯基溴化膦-2’,5’-二甲氧基苯基)-9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物(化合物D)、0.2g(15.4mmol)4-氰基苯甲醛和30ml无水四氢呋喃放入氩气氛围下的50ml单口圆底烧瓶中并于其中搅拌后,向其中缓缓滴入0.66ml(21%的乙醇溶液,16.8mml)21%的乙醇钠。于常温将它们搅拌2小时。反应完成后,将其在减压下蒸发。利用展开液(乙酸乙酯/正己烷:1/1)由该混合物获得目标化合物,即,0.42g(收率:65%)作为白色固体的10-{4’-[2-(4-氰基苯基)-乙烯基]-2’,5’-二甲氧基苯基}-9-氧杂-10-磷杂菲-10-氧化物(化合物103)。
1H NMR(CDCl3),δ=3.30(s,3H,OCH3),3.94(s,3H,OCH3),6.92~7.93(m,16H,乙烯基和芳基)
[第四实施方式]10-{4’-[2-(3-苯基乙烯基)]-2’,5’-二甲氧基苯基}-9-氧杂-10-磷杂菲-10-氧化物)-乙烯基]-2’,5’-二甲氧基苯基}-9-氧杂-10-磷杂菲-10-氧化物(化合物104)的合成
在将1g(14mmol)10-(4’-三苯基溴化膦-2’,5’-二甲氧基苯基)-9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物(化合物D)、0.1g(15.4mmol)苯1,3-甲醛和50ml无水四氢呋喃放入氩气氛围下的50ml单口圆底烧瓶中并于其中搅拌后,向其中缓缓滴入0.66ml(21%的乙醇溶液,16.8mml)21%的乙醇钠。于常温将它们搅拌2小时。反应完成后,将其在减压下蒸发。利用展开液(乙酸乙酯/正己烷:1/1)由该混合物获得目标化合物,即,0.23g(收率:20%)作为白色固体的10-{4’-[2-(3-苯基乙烯基)]-2’,5’-二甲氧基苯基}-9-氧杂-10-磷杂菲-10-氧化物)-乙烯基]-2’,5’-二甲氧基苯基}-9-氧杂-10-磷杂菲-10-氧化物(化合物104)。
1H NMR(CDCl3),δ=3.22(s,3H,OCH3),3.70(s,3H,OCH3),6.40~7.96(m,28H,乙烯基和芳基)
[第五实施方式]10-{4’-[2-(FIrpic)]-2’,5’-二甲氧基苯基}-9-氧杂-10-磷杂菲-10-氧化物(化合物105)的合成
将0.72g(0.11mmol)FIrpic醇和0.5g(0.11mmol)10-(4’-溴甲基-2’,5’-二甲氧基苯基)-9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物与15ml二甲基甲酰胺在100ml烧瓶中混合,并向该烧瓶中加入0.46g(0.33mmol)碳酸钾。加入后,通过在100℃加热回流48小时使其反应。反应后,向其中加入100ml二氯甲烷,然后用水洗涤以产生滤液。通过硫酸镁除去滤液中的水。在减压下除去二氯甲烷并进行浓缩,从而获得目标化合物,即,0.98g(收率:81%)作为黄色固体的10-{4’-[2-(FIrpic)]-2’,5’-二甲氧基苯基}-9-氧杂-10-磷杂菲-10-氧化物(化合物105)。
1H NMR(CDCl3),δ=3.24(s,3H,OCH3),3.71(s,3H,OCH3),4.52(s,2H,CH2),6.40~7.96(m,27H,乙烯基和芳基)
[第六实施方式]10-联苯基-(4-(9-氧杂-10-磷杂菲)-9-氧杂-10-磷杂菲-10-氧化物(化合物106)的合成
将10g(0.05mol)9,10-二羟基-9-氧杂-10-磷杂菲-10-氧化物、6.4g(0.05mol)碳酸钾、9.38g(0.023mol)4-4’-碘联苯、1.6g(23mmol)钯催化剂和60ml二氧六环放入氩气氛围下的100ml单口圆底烧瓶中。将它们加热回流24小时。反应完成后,将其于常温缓缓冷却,在减压下蒸馏,并溶解在二氯甲烷溶液中,使用蒸馏水洗涤数次。通过硫酸镁对其进行干燥并过滤,以在减压下除去和浓缩溶剂,并通过硅胶柱色谱法(乙酸乙酯∶己烷=1∶1)提纯,从而获得目标化合物,即,18.32g(收率:68%)作为白色固体的10-联苯基-(4-(9-氧杂-10-磷杂菲)-9-氧杂-10-磷杂菲-10-氧化物(化合物106)。
1H NMR(CDCl3),δ=6.56(d,1H,芳基),7.01~7.99(m,23H,芳基)
[第七实施方式]9,9-二己基-(2,7-(9-氧杂-10-磷杂菲)-9-氧杂-10-磷杂菲-10-氧化物)芴(化合物107)的合成
将10g(0.05mol)9,10-二羟基-9-氧杂-10-磷杂菲-10-氧化物、6.4g(0.05mmol)碳酸钾、13.5g(0.023ml)4,4’-碘-9,9’-二己基芴、1.6g(23mmol)钯催化剂和100ml二氧六环放入氩气氛围下的100ml单口圆底烧瓶中。将它们加热回流48小时。反应完成后,将其于常温缓缓冷却,在减压下蒸馏,并溶解在二氯甲烷溶液中,然后使用蒸馏水洗涤数次。通过硫酸镁对其进行干燥并过滤,以在减压下除去和浓缩溶剂,然后通过硅胶柱色谱法(乙酸乙酯∶己烷=1∶1)提纯,从而获得目标化合物,即,14.4g(收率:40%)作为白色固体的9,9-二己基-(2,7-(9-氧杂-10-磷杂菲)-9-氧杂-10-磷杂菲-10-氧化物)芴(化合物107)。
1H NMR(CDCl3),δ=0.35~2.1(m,26H,二己基),7.05~8.29(m,22H,芳基)
[第八实施方式]10-(2-对-9-氧杂-10-磷杂菲-乙烯基)-9-氧杂-10-磷杂菲-10-氧化物(化合物108)的合成
(10-氧-10H-9-氧杂-10-磷杂菲-10-基)-甲醇(化合物E)的合成
将20g(0.09mol)9-氧杂-10-磷杂菲-10-氧化物和3.0g(0.10mol)多聚甲醛溶解在100ml蒸馏水中,然后加热回流6小时。反应完成后,将其于常温冷却,同时缓缓添加乙醚以产生沉淀。过滤产生的沉淀,并在减压烘箱中进行干燥,从而获得目标化合物,即,20.3g(收率:89%)作为白色固体的(10-氧-10H-9-氧杂-10-磷杂菲-10-基)-甲醇(化合物E)。
(10-氧-10H-9-氧杂-10-磷杂菲-10-基)-甲醛(化合物F)的合成
使用干冰和丙酮冷却100ml纯化的无水二氯甲烷。冷却完成后,加入42.5ml(0.05mol)乙二酰氯和5.76ml(0.08mol)二甲基亚砜。然后,将它们搅拌10分钟。接下来,向其中加入10g(0.04mol)(10-氧-10H-9-氧杂-10-磷杂菲-10-基)-甲醇(化合物E)。之后,将它们搅拌1小时。然后,向其中缓缓加入22ml三乙胺。随后,于常温将它们搅拌12小时。反应完成后,向其中加入100ml蒸馏水。然后,使用二氯甲烷萃取溶液。使用1N盐酸水溶液、饱和碳酸氢钠溶液或饱和盐水等处理萃取液,并使用无水硫酸镁对其进行干燥。在减压下过滤经干燥的溶液,并在减压下对其进行蒸发,从而获得棕色溶液。将获得的产物用于紧随其后的步骤中的反应。
10-(2-对-9-氧杂-10-磷杂菲-乙烯基)-9-氧杂-10-磷杂菲-10-氧化物(化
合物108)的合成
加入7.73g(0.03mol)上述产物、12.7g(0.02mol)鏻盐和100ml无水四氢呋喃以制得悬浮液。然后,对它们进行搅拌,同时向其中滴入21%的乙醇钠溶液。滴入完成后将它们搅拌24小时。然后,添加100ml乙酸乙酯。接下来,使用蒸馏水洗涤数次,使用无水硫酸镁干燥该溶液,在减压下过滤并在减压下蒸发,从而获得深黄色固体。使用乙酸乙酯∶己烷(1∶1)展开液提纯产生的固体以除去副产物(即,三苯基氧化物),从而获得目标化合物,即,6.42g(收率:32%)作为白色固体的10-(2-对-9-氧杂-10-磷杂菲-乙烯基)-9-氧杂-10-磷杂菲-10-氧化物(化合物108)。
1H NMR(CDCl3),δ=5.40(d,4H,乙烯基),6.88~8.89(m,24H,芳基)
[第九实施方式]10-{4’-[2-萘基]-2’,5’-二甲氧基苯基}-9-氧杂-10-磷杂菲-10-氧化物(化合物109)的合成
将3.97g(0.02mol)9,10-二羟基-9-氧杂-10-磷杂菲-10-氧化物、4.05g(0.02mol)2-萘基-1,4-苯醌和10ml 2-乙氧基乙醇放入氩气氛围下的100ml单口圆底烧瓶中。将它们加热回流12小时。反应完成后,将其于常温缓缓冷却以产生沉淀。使用甲醇在减压下过滤该沉淀,从而获得3.61g浅色粉末。向该粉末中依次加入4.5g(0.03mol)碘甲烷、4.43g(0.03mol)碳酸钾和50ml丙酮,并对其加热回流4小时。反应完成后,使用二氯甲烷和蒸馏水对其进行萃取。使用无水硫酸镁干燥,然后在减压下过滤以除去溶剂,从而获得目标化合物,即,3.6g(收率:44%)作为白色固体的10-{4’-[2-萘基]-2’,5’-二甲氧基苯基}-9-氧杂-10-磷杂菲-10-氧化物(化合物109)。
1H NMR(CDCl3):δ=2.15(s,3H,OCH3),6.24(d,1H,芳基),6.75(d,1H,芳基),7.08~7.96(m,8H,芳基)
[第十实施方式]10-(1,4-二甲氧基蒽-2-基)-9-氧杂-10-磷杂菲-10-氧化物(化合物111)的合成
1,4-蒽醌(化合物I)的合成
将25g 1,4-二羟基-蒽醌和250ml无水甲醇放入氩气氛围下的500ml圆底烧瓶中,并在0℃缓缓添加15.7g NaBH4。经过1小时后,在0℃向该混合物中缓缓加入6N HCl,以产生橙色沉淀。过滤该沉淀,然后使用水和甲醇进行洗涤。将该沉淀物再沉淀于二氯甲烷和醚中,从而获得目标化合物,即,15.3g(收率:70%)作为橙色固体的1,4-蒽醌(化合物I)。
1H NMR(CDCl3):δ=7.06(d,2H),7.70(q,2H),8.06(q,2H),8.60(s,2H)
2-(10-氧-10H-9-氧杂-10-磷杂菲-10-基)蒽-1,4-二醇(化合物J)的合
成
将17g 1,4-蒽醌(化合物I)、21g的9-氧杂-10-磷杂菲-10-氧化物和110ml 2-丁氧基乙醇放入氩气氛围下的500ml圆底烧瓶中。然后,将它们加热回流4小时。在高温真空下除去2-丁氧基乙醇,然后利用柱色谱(乙酸乙酯∶正己烷=1∶1)提纯,从而获得目标化合物,即,14.6g(收率:42%)作为固体的2-(10-氧-10H-9-氧杂-10-磷杂菲-10-基)蒽-1,4-二醇(化合物J)。
1H NMR(丙酮-d6):δ=8.46(s,1H),8.25(d,1H),8.20(t,1H),8.04(d,1H),7.89(t,1H),7.84(s,1H),7.78(t,1H),7.64(d,1H),7.55(m,1H),7.49(m,5H),7.29(d,2H),6.73(d,1H)
10-(1,4-二甲氧基蒽-2-基)-9-氧杂-10-磷杂菲-10-氧化物(化合物111)
的合成
将5g 2-(10-氧-10H-9-氧杂-10-磷杂菲-10-基)-蒽-1,4-二醇、6.5gK2CO3、5ml CH3I和100ml丙酮放入250ml圆底烧瓶中。然后,将它们加热回流4小时。反应完成后,除去丙酮。接下来,使用水和乙酸乙酯对其进行萃取,然后再沉淀于THF和己烷中,从而获得1.5g(收率:30%)作为固体的10-(1,4-二甲氧基蒽-2-基)-9-氧杂-10-磷杂菲-10-氧化物(化合物111)。
1H NMR(丙酮-d6):δ=8.73(s,1H),8.27(q,1H),8.22(t,1H),8.07(q,1H),8.01(t,1H),7.84(s,1H),7.80(t,1H),7.67(d,1H),7.57(m,1H),7.50(m,3H),7.40(d,1H),7.30(d,1H),6.77(d,1H),4.05(s,6H)
[第十一实施方式]10-(1,4-二甲氧基-7-甲基-蒽-2-基)-9-氧杂-10-磷杂菲-10-氧化物(化合物112)的合成
1,4-二羟基-6-甲基-蒽醌(化合物K)
将50g的4-甲基邻苯二甲酸酐、34g氢醌、120g氯化铝和24g NaCl放入500ml锥形瓶中。将它们在250℃搅拌10分钟。在反应进行过程中产生红色固体。降低加热温度,然后向其中加入水和HCl以产生橙色固体。对其进行过滤,然后再沉淀于THF和己烷中,从而获得目标化合物,即,16.7g(收率:35%)作为橙色固体的1,4-二羟基-6-甲基-蒽醌(化合物K)。
1H NMR(CDCl3):δ=12.92(s,1H),12.88(s,1H),8.21(d,1H),8.11(s,1H),7.61(d,1H),7.28(s,1H),2.54(s,3H)
通过与第十实施方式相同的方法,制备6-甲基-1,4-蒽醌(化合物L)、7-甲基-2-(10-氧-10H-9-氧杂-10-磷杂菲-10-基)-蒽-1,4-二醇(化合物M)和10-(1,4-二甲氧基-7-甲基-蒽-2-基)-9-氧杂-10-磷杂菲-10-氧化物(化合物112)。
[测试例]紫外和光致发光性质测试
本发明所合成的化合物的UV-vis和光致发光(下文称为PL)的测量值列于表1中。使用Shimatzu UV/Vis分光光度计来测量UV-vis,使用来自Perkin Elmer Co.的LS55发光分光计来测量PL。使用二氯甲烷溶液制备测量样品。以波长为单位获得制备的样品的UV-vis谱和PL性质,其中UV-vis峰表示极值。
[表1]化合物结构和UV/PL数据
电致发光性质评价I
为进行电致发光(下文称作EL)性质测试,如下制备最常用形式的有机发光二极管,所述二极管由阴极、空穴注入层、空穴输送层、发光层、电子输送层、电子注入层和阳极构成。
通过在图案化的ITO透明电极上沉积膜厚为60nm的4,4’,4”-三(N-(2-萘基)-N-苯基-氨基)-三苯胺膜(下文称为‘2-TNATA膜’)来形成空穴注入层,并在该2-TNATA膜上形成膜厚为15nm的4,4-二[N-(1-萘基)-N-苯基-氨基]联苯膜(下文称为‘NPD膜’)。NPD膜起到空穴输送层的作用。
接下来,通过在NPD膜上沉积膜厚为30nm的化合物101、化合物103或化合物104来形成发光层,并在该膜上沉积膜厚为5nm的2,9-二甲基-4,7-二苯基-1,10-二氮杂菲膜(下文称为‘BCP膜’),以形成空穴阻止层。然后,在该膜上沉积膜厚为30nm的三(8-羟基喹啉)铝膜(下文称为‘Alq膜’),以形成电子注入层。
最后,在该膜上形成厚1nm的Li/F膜,并于其上沉积金属铝(膜厚为200nm),以形成金属阴极,由此制备有机发光二极管。
电致发光性质评价II
为进行电致发光(下文称作EL)性质测试,如下制备最常用形式的有机发光二极管,所述二极管由阴极、空穴注入层、空穴输送层、发光层、电子输送层、电子注入层和阳极构成。
通过在图案化的ITO透明电极上沉积膜厚为40nm的4,4’,4”-三(N-(2-萘基)-N-苯基-氨基)-三苯胺膜(下文称为‘2-TNATA膜’)来形成空穴注入层,并在该2-TNATA膜上形成膜厚为10nm的4,4-二[N-(1-萘基)-N-苯基-氨基]联苯膜(下文称为‘NPD膜’)。NPD膜起到空穴输送层的作用。
接下来,通过在NPD膜上沉积膜厚为40nm的化合物112来形成发光层,并在该膜上沉积膜厚为10nm的4,7-二苯基-1,10-二氮杂菲膜(下文称为‘BPhen膜’),以形成空穴阻止层。
最后,在该膜上形成厚1nm的Li/F膜,并于其上沉积金属铝(膜厚为200nm),以形成金属阴极,由此制备有机发光二极管。
下表2表示了化合物112的电致发光性质。
[表2]
开启(V) | E.Q.E | 效率(cd/A) | 效率(lm/A) | 色度坐标(CIE) | ELmax(nm) | |
化合物112 | 3.4 | 1.56 | 2.06 | 1.13 | 0.16,0.16 | 450 |
工业实用性
本发明的新型磷杂菲化合物可以用作OLED的核心材料,也可以用作用于光学开关、传感器、模块、波导器或光存储器的材料,或者用于放大、非线性光学材料、光电导体或光吸收器等。
Claims (6)
1.由以下化学式1表示的磷杂菲化合物,
在化学式1中,其中选自以下结构:
B是化学键或NR71、(O=)PR71、SiR73R74、SO2或O;
D是CR81R82、NR83、O、S或SO2;
R31是C1-C22烷基、C6-C30芳基、C2-C10烯基或C1-C22烷羰基,并且R31的烷基、烯基或烷羰基不被取代或进一步被选自下述基团的至少一种取代:包含N、O和S的至少一种的3元至5元杂环烷基、C3-C22环烷基、C2-C10炔基、C2-C10烯基、氰基或卤素;
R41~R54,R56~R64彼此独立且为氢、C1-C22烷基、C6-C30芳基、卤素、C2-C30杂芳基、氰基、羧酸、C1-C10烷基甲硅烷基、C6-C30芳基甲硅烷基、C6-C30芳基C1-C22烷基、C1-C22烷基C6-C30芳基或OR31,或者R45和R46或R47和R48与C3-C5亚烷基或C3-C5亚烯基偶联以形成稠环,并且所述稠环的碳不被替换或被替换为选自氧、硫或氮的杂原子;
R71~R74彼此独立且为C1-C22烷基、C3-C22环烷基、C6-C30芳基、单或二C1-C10烷基氨基、单或二C6-C30芳基氨基或氨基,并且R71~R74的烷基、环烷基或芳基不被取代或进一步被选自下述基团的至少一种取代:卤素、C1-C22烷基、C6-C30芳基、C1-C22烷氧基、包含氧、氮或硫的至少一种的3元至7元杂环烷基,或氰基;
R81~R83彼此独立且为氢、C1-C22烷基、C6-C30芳基、卤素、C2-C30杂芳基、氰基、羧酸、C1-C10烷基甲硅烷基、C6-C30芳基甲硅烷基、C6-C30芳基C1-C22烷基、C1-C22烷基C6-C30芳基或C1-C22烷氧基;并且
m为1~4的整数;
R1是氢、C1-C22烷基、C6-C30芳基、C2-C30杂芳基、卤素、氰基、C1-C22烷氧基、C6-C30芳氧基、C6-C30芳磺酰基、单或二C1-C10烷基氨基、单或二C6-C30芳基氨基、C2-C7烯氧基、C2-C7炔氧基、C2-C7烯羰氧基、C2-C7炔羰氧基、C1-C10烷基甲硅烷基、C6-C30芳基甲硅烷基或并且R1的烷基、芳基、杂芳基、烷氧基、芳氧基、芳磺酰基、烷基氨基、芳基氨基、烯氧基、炔氧基、烷基甲硅烷基或芳基甲硅烷基不被取代或进一步被选自下述基团的至少一种取代:C1-C10烷基、卤素、氰基、硝基、羧酸、C6-C30芳基、单或二C1-C10烷基氨基、单或二C6-C30芳基氨基、C1-C10烷基甲硅烷基或C6-C30芳基甲硅烷基;
L11是化学键或C2-C10亚烯基、C6-C30亚芳基或NR16,并且L11的亚烯基或亚芳基不被取代或进一步被选自下述基团的至少一种取代:C1-C22烷基、C1-C22烷氧基、C3-C22环烷基、C6-C30芳基、氰基、卤素、氨基、单或二C1-C10烷基氨基、单或二C6-C30芳基氨基、硝基或羟基;
R2~R9彼此独立且为氢、C1-C22烷基、包含氧、氮或硫的C1-C22烷基、C1-C22烷氧基、C3-C22环烷基、C3-C22环烷基C1-C22烷基、C6-C30芳基、卤素、氰基、氨基、单或二C1-C10烷基氨基、单或二C6-C30芳基氨基、羟基、硝基、单或二苄基氨基或C3-C10环烷基氨基,并且R2~R9通过C3-C5亚烷基或C3-C5亚烯基与相邻取代基的碳结合以形成稠环,稠环的碳不被替换或被替换为选自氧、硫或氮的杂原子,R2~R9的烷基、烷氧基、环烷基、环烷基烷基、芳基或氨基不被取代或进一步被选自下述基团的至少一种取代:C1-C10烷基、卤素、C6-C30芳基、C1-C10烷基甲硅烷基或C6-C30芳基甲硅烷基;
R16为C1-C22烷基、C3-C22环烷基、C6-C30芳基、单或二C1-C10烷基氨基、单或二C6-C30芳基氨基或氨基,并且R11~R16的烷基、环烷基或芳基不被取代或进一步被选自下述基团的至少一种取代:卤素、C1-C22烷基、C6-C30芳基、C1-C22烷氧基、包含氧、氮或硫的至少一种的3元至7元杂环烷基,或氰基;和
R21~R28彼此独立且为氢、C1-C22烷基、包含氧、氮或硫的C1-C22烷基、C1-C22烷氧基、C3-C22环烷基、C3-C22环烷基C1-C22烷基、C6-C30芳基、卤素、氰基、氨基、单或二C1-C10烷基氨基、单或二C6-C30芳基氨基、羟基、硝基、单或二苄基氨基或C3-C10环烷基氨基,并且R21~R28通过C3-C5亚烷基或C3-C5亚烯基与相邻取代基的碳结合以形成稠环,稠环的碳不被替换或被替换为选自氧、硫或氮的杂原子,R21~R28的烷基、烷氧基、环烷基、环烷基烷基、芳基或氨基不被取代或进一步被选自下述基团的至少一种取代:C1-C10烷基、卤素、C6-C30芳基、C1-C10烷基甲硅烷基或C6-C30芳基甲硅烷基。
4.一种包含权利要求1~3中任一项所述的磷杂菲化合物的有机发光二极管。
5.如权利要求4所述的有机发光二极管,其中,所述磷杂菲化合物包含在选自电子输送层、发光层或其混合功能层的层中。
6.一种包含权利要求1~3中任一项所述的磷杂菲化合物的有机半导体器件。
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