CN111819167A - 用于有机电致发光器件的材料 - Google Patents
用于有机电致发光器件的材料 Download PDFInfo
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- CN111819167A CN111819167A CN201980017275.7A CN201980017275A CN111819167A CN 111819167 A CN111819167 A CN 111819167A CN 201980017275 A CN201980017275 A CN 201980017275A CN 111819167 A CN111819167 A CN 111819167A
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- 239000000463 material Substances 0.000 title claims description 55
- 150000001875 compounds Chemical class 0.000 claims abstract description 118
- 125000003118 aryl group Chemical group 0.000 claims description 73
- 150000003254 radicals Chemical class 0.000 claims description 35
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- 125000004429 atom Chemical group 0.000 claims description 20
- 239000002019 doping agent Substances 0.000 claims description 19
- 238000006467 substitution reaction Methods 0.000 claims description 19
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 18
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 14
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- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 13
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- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 10
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- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 7
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- 125000000217 alkyl group Chemical group 0.000 claims description 6
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- 125000004122 cyclic group Chemical group 0.000 claims description 6
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- 125000004104 aryloxy group Chemical group 0.000 claims description 5
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- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 4
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- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 claims description 4
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- 125000001424 substituent group Chemical group 0.000 claims description 4
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- WUNJCKOTXFSWBK-UHFFFAOYSA-N indeno[2,1-a]carbazole Chemical compound C1=CC=C2C=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 WUNJCKOTXFSWBK-UHFFFAOYSA-N 0.000 claims description 3
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- 125000002950 monocyclic group Chemical group 0.000 claims description 3
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- 238000010791 quenching Methods 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
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- 239000010410 layer Substances 0.000 description 131
- -1 transition metal cations Chemical class 0.000 description 45
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 31
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- 230000005525 hole transport Effects 0.000 description 22
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- 125000001072 heteroaryl group Chemical group 0.000 description 12
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 12
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- 239000000243 solution Substances 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 239000000412 dendrimer Substances 0.000 description 8
- 229920000736 dendritic polymer Polymers 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 229910052709 silver Inorganic materials 0.000 description 8
- 230000000903 blocking effect Effects 0.000 description 7
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 241000723343 Cichorium Species 0.000 description 6
- 235000007542 Cichorium intybus Nutrition 0.000 description 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 5
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- 239000011159 matrix material Substances 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 5
- 229910052697 platinum Inorganic materials 0.000 description 5
- 238000000859 sublimation Methods 0.000 description 5
- 230000008022 sublimation Effects 0.000 description 5
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical class N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 150000001716 carbazoles Chemical class 0.000 description 4
- 125000004986 diarylamino group Chemical group 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 238000001906 matrix-assisted laser desorption--ionisation mass spectrometry Methods 0.000 description 4
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 239000011368 organic material Substances 0.000 description 4
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 4
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- 229910052723 transition metal Inorganic materials 0.000 description 4
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 3
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- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
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- 239000003480 eluent Substances 0.000 description 3
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
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- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
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- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical class C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 2
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- ZKAMEFMDQNTDFK-UHFFFAOYSA-N 1h-imidazo[4,5-b]pyrazine Chemical class C1=CN=C2NC=NC2=N1 ZKAMEFMDQNTDFK-UHFFFAOYSA-N 0.000 description 2
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 2
- LFFXHHIUSOGZOX-UHFFFAOYSA-N 2,8-bis(benzenesulfonyl)indeno[2,1-b]fluorene-10,12-dione Chemical compound C1(=CC=CC=C1)S(=O)(=O)C=1C=C2C(C3=CC=4C(C5=CC(=CC=C5C=4C=C3C2=CC=1)S(=O)(=O)C1=CC=CC=C1)=O)=O LFFXHHIUSOGZOX-UHFFFAOYSA-N 0.000 description 2
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 2
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 2
- LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical compound C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 description 2
- DXYYSGDWQCSKKO-UHFFFAOYSA-N 2-methylbenzothiazole Chemical compound C1=CC=C2SC(C)=NC2=C1 DXYYSGDWQCSKKO-UHFFFAOYSA-N 0.000 description 2
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 2
- HCCNHYWZYYIOFM-UHFFFAOYSA-N 3h-benzo[e]benzimidazole Chemical class C1=CC=C2C(N=CN3)=C3C=CC2=C1 HCCNHYWZYYIOFM-UHFFFAOYSA-N 0.000 description 2
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- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
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- 229910052796 boron Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
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- 229910052791 calcium Inorganic materials 0.000 description 1
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- CJRHLSZJEFJDLA-UHFFFAOYSA-N methyl 5-bromo-2-iodobenzoate Chemical compound COC(=O)C1=CC(Br)=CC=C1I CJRHLSZJEFJDLA-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000005054 naphthyridines Chemical class 0.000 description 1
- 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
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- 229910052762 osmium Inorganic materials 0.000 description 1
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- 125000005581 pyrene group Chemical group 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- GDISDVBCNPLSDU-UHFFFAOYSA-N pyrido[2,3-g]quinoline Chemical compound C1=CC=NC2=CC3=CC=CN=C3C=C21 GDISDVBCNPLSDU-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000003380 quartz crystal microbalance Methods 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- YSZJKUDBYALHQE-UHFFFAOYSA-N rhenium trioxide Chemical compound O=[Re](=O)=O YSZJKUDBYALHQE-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
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 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
- 239000010944 silver (metal) Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- CHLCPTJLUJHDBO-UHFFFAOYSA-M sodium;benzenesulfinate Chemical compound [Na+].[O-]S(=O)C1=CC=CC=C1 CHLCPTJLUJHDBO-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 150000001629 stilbenes Chemical class 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 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
- 238000002061 vacuum sublimation Methods 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
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- 150000003754 zirconium Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
- C07D213/71—Sulfur atoms to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/40—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by doubly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
本发明涉及适用于电子器件、特别是有机电致发光器件中的式(1)化合物,并且涉及包含这些化合物的电子器件。
Description
本发明涉及一种式(1)化合物、所述化合物在电子器件中的用途以及包含式(1)化合物的电子器件。本发明还涉及一种包含一种或多种式(1)化合物的制剂。
用于电子器件的功能性化合物的开发目前是深入研究的主题。其目的特别是开发如下化合物,用所述化合物可以实现电子器件在一个或多个相关方面的改进特性,诸如器件的功率效率和寿命以及发射光的色坐标。
根据本发明,术语电子器件被认为尤其指有机集成电路(OIC)、有机场效应晶体管(OFET)、有机薄膜晶体管(OTFT)、有机发光晶体管(OLET)、有机太阳能电池(OSC)、有机光学检测器、有机光感受器、有机场猝熄器件(OFQD)、有机发光电化学电池(OLEC)、有机激光二极管(O-laser)以及有机电致发光器件(OLED)。
特别令人感兴趣的是提供用于最后提及的称为OLED的电子器件中的化合物。OLED的一般结构和功能原理是本领域技术人员已知的,并且例如在US 4539507中进行了描述。
已知具有空穴传输性功能的层(空穴传输性层),例如空穴注入层、空穴传输层和电子阻挡层对电子器件的性能数据有很大影响。
实际上,OLED的效率和寿命尤其取决于器件中电子和空穴的电荷-载流子平衡。此平衡通过器件中电荷-载流子分布和相关场分布来建立。
有效的空穴注入是OLED制造中的主要挑战。常用的透明阳极材料氧化锡铟的逸出功的绝对值通常低于常见空穴传输材料的最高占据分子轨道(HOMO)能量的绝对值。
因此,对于将空穴注入到空穴传输层中存在势垒,这导致OLED的工作电压增加。此问题通常通过用p型掺杂剂掺杂空穴传输层(例如,如WO 2014/056565中),或在阳极与空穴传输层之间施加空穴注入层(例如,如在WO 2001/49806中)来解决。
为了获得良好的性能数据,空穴传输层中的电荷载流子的良好迁移率和良好的空穴注入特性特别重要。
现有技术公开了p型掺杂剂(电子受体化合物)与空穴传输材料的组合在OLED的空穴传输性层(空穴注入层、空穴传输层和电子阻挡层)中的用途。在本文中,p型掺杂剂应理解为是指当作为次要组分添加到主要组分中时显著增加其电导率的化合物。
电子受体化合物还可以用作空穴传输性层中(例如空穴注入层中)的主要组分,以获得具有特别良好的空穴注入特性的层。
现有技术中已知p型掺杂剂,以及更一般地,有机电子受体化合物,例如7,7,8,8-四氰基-2,3,5,6-四氟醌二甲烷(F4TCNQ)。现有技术还例如在WO 2011/33023中公开了过渡金属阳离子和主族金属阳离子的金属络合物作为电子受体化合物,以及例如在EP 2045848中公开了茚并芴二酮衍生物。
然而,需要可以在OLED中用作电子受体材料的替代材料。此外,仍需要对此类化合物进行进一步改进以在寿命和效率方面改进OLED性能。需要由于适当的电子特性,例如通过具有高电子亲和力而有效作为电子受体材料的材料。同时,这些材料还应表现出适当的物理化学特性,例如在溶解性和稳定性方面,以在OLED制造期间进行最佳合成、纯化和处理。这些材料还应表现出适当的形态(分子平面性)。此外,OLED中用作电子受体材料(例如在空穴注入层中用作p型掺杂剂或用作主要组分)的材料应尽可能少地吸收可见光区域(VIS区域)中的光。非常需要在VIS区域中没有明显的吸收带,因为VIS区域中的吸收会影响OLED的发光特征及其效率。
因此,本发明是基于以下技术目的:提供一种用于电子器件中的在选自空穴注入层、空穴传输层和电子阻挡层中的空穴传输性层中作为p型掺杂剂或作为主要组分的电子受体材料。
在关于用于电子器件中的新型化合物的研究中,现已出乎意料地发现,以下定义的式(1)化合物非常适用于电子器件中。特别地,所述化合物实现了上文提及的技术目的中的一个或多个,优选全部技术目的。
因此,本申请涉及式(1)的化合物,
其中以下适用于所用符号和标记:
W为CR1、CR2或N;
V为CR、N,并且至少两个相邻的基团V表示式(V-1)的基团,
X1、X2在每次出现时相同或不同地选自式(X-1)至(X-9)的基团;
其中式(X-1)至(X-9)中的虚线键指示与包含X1或X2的5元环连接的键;
R、R1在每次出现时相同或不同地表示H,D,F,Cl,Br,I,CHO,CN,N(Ar)2,C(=O)Ar,P(=O)(Ar)2,S(=O)Ar,S(=O)2Ar,NO2,Si(R3)3,B(OR3)2,OSO2R3,具有1至40个C原子的直链的烷基、烷氧基或硫代烷基基团或具有3至40个C原子的支链或环状的烷基、烷氧基或硫代烷基基团,所述烷基、烷氧基或硫代烷基基团中的每一个可以被一个或多个基团R3取代,其中在每种情况下一个或多个非相邻的CH2基团可以被R3C=CR3、C≡C、Si(R3)2、Ge(R3)2、Sn(R3)2、C=O、C=S、C=Se、P(=O)(R3)、SO、SO2、O、S或CONR3代替,并且其中一个或多个H原子可以被D、F、Cl、Br、I、CN或NO2代替,具有5至60个芳族环原子的芳族或杂芳族环系,在每种情况下所述芳族或杂芳族环系可以被一个或多个基团R3取代,或具有5至40个芳族环原子的芳氧基基团,所述芳氧基基团可以被一个或多个基团R3取代,其中两个基团R和/或两个基团R1可以形成单环或多环的脂族环系或芳族环系,所述脂族环系或芳族环系可以被一个或多个基团R3取代;
R2在每次出现时相同或不同地表示-C(=O)Ar1、-P(=O)(Ar1)2、-S(=O)Ar1、-S(=O)2Ar1、-SAr1、-B(Ar1)2或-P(Ar1)2;
R3在每次出现时相同或不同地表示H,D,F,Cl,Br,I,CHO,CN,N(Ar)2,C(=O)Ar,P(=O)(Ar)2,S(=O)Ar,S(=O)2Ar,NO2,Si(R4)3,B(OR4)2,OSO2R4,具有1至40个C原子的直链的烷基、烷氧基或硫代烷基基团或具有3至40个C原子的支链或环状的烷基、烷氧基或硫代烷基基团,所述烷基、烷氧基或硫代烷基基团中的每一个可以被一个或多个基团R4取代,其中在每种情况下一个或多个非相邻的CH2基团可以被R4C=CR4、C≡C、Si(R4)2、Ge(R4)2、Sn(R4)2、C=O、C=S、C=Se、P(=O)(R4)、SO、SO2、O、S或CONR4代替,并且其中一个或多个H原子可以被D、F、Cl、Br、I、CN或NO2代替,具有5至60个芳族环原子的芳族或杂芳族环系,在每种情况下所述芳族或杂芳族环系可以被一个或多个基团R4取代,或具有5至60个芳族环原子的芳氧基基团,所述芳氧基基团可以被一个或多个基团R4取代,其中两个基团R3可以形成单环或多环的脂族环系或芳族环系,所述脂族环系或芳族环系可以被一个或多个基团R4取代;
R4在每次出现时相同或不同地表示H,D,F,Cl,Br,I,CN,具有1至20个C原子的直链的烷基、烷氧基或硫代烷基基团或具有3至20个C原子的支链或环状的烷基、烷氧基或硫代烷基基团,其中在每种情况下一个或多个非相邻的CH2基团可以被SO、SO2、O、S代替,并且其中一个或多个H原子可以被D、F、Cl、Br或I代替,或具有5至24个C原子的芳族或杂芳族环系;
Ar、Ar1在每次出现时相同或不同地为具有5至60个芳族环原子的芳族或杂芳族环系,所述芳族或杂芳族环系在每种情况下还可以被一个或多个基团R4取代;
并且其中式(1)和(V-1)中包含基团W的两个6元环均带有至少一个取代基R2。
本发明意义上的相邻取代基是与彼此直接连接的原子键合或与同一个原子键合的取代基。
此外,以下化学基团的定义适用于本申请的目的:
本发明意义上的芳基基团含有6至60个芳族环原子,优选6至40个芳族环原子,更优选6至20个芳族环原子;本发明意义上的杂芳基基团含有5至60个芳族环原子,优选5至40个芳族环原子,更优选5至20个芳族环原子,其中至少一个是杂原子。杂原子优选选自N、O和S。这表示基本定义。如果在本发明的说明书中指示其他优选情况,例如关于存在的芳族环原子或杂原子的数目,则这些情况为适用的。
本文中的芳基基团或杂芳基基团被认为是指简单的芳族环,即苯;或简单的杂芳族环,例如吡啶、嘧啶或噻吩;或稠合(增环)的芳族或杂芳族多环,例如萘、菲、喹啉或咔唑。在本申请的意义上,稠合(增环)的芳族或杂芳族多环由彼此稠合的两个或更多个简单的芳族或杂芳族环组成。
在每种情况下可以被上文提及的基团取代并且可以通过任何期望位置与芳族或杂芳族环系连接的芳基或杂芳基基团,被认为特别指衍生自以下物质的基团:苯、萘、蒽、菲、芘、二氢芘、苣、苝、荧蒽、苯并蒽、苯并菲、并四苯、并五苯、苯并芘、呋喃、苯并呋喃、异苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、异苯并噻吩、二苯并噻吩、吡咯、吲哚、异吲哚、咔唑、吡啶、喹啉、异喹啉、吖啶、菲啶、苯并-5,6-喹啉、苯并-6,7-喹啉、苯并-7,8-喹啉、吩噻嗪、吩嗪、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑、菲并咪唑、吡啶并咪唑、吡嗪并咪唑、喹喔啉并咪唑、唑、苯并唑、萘并唑、蒽并唑、菲并唑、异唑、1,2-噻唑、1,3-噻唑、苯并噻唑、哒嗪、苯并哒嗪、嘧啶、苯并嘧啶、喹喔啉、吡嗪、吩嗪、萘啶、氮杂咔唑、苯并咔啉、菲咯啉、1,2,3-***、1,2,4-***、苯并***、1,2,3-二唑、1,2,4-二唑、1,2,5-二唑、1,3,4-二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、1,3,5-三嗪、1,2,4-三嗪、1,2,3-三嗪、四唑、1,2,4,5-四嗪、1,2,3,4-四嗪、1,2,3,5-四嗪、嘌呤、蝶啶、吲哚嗪和苯并噻二唑。
根据本发明的定义的芳氧基基团被认为是指通过氧原子键合的如上文所定义的芳基基团。类似的定义适用于杂芳氧基基团。
本发明意义上的芳族环系在环系中含有6至60个C原子,优选6至40个C原子,更优选6至20个C原子。本发明意义上的杂芳族环系含有5至60个芳族环原子,优选5至40个芳族环原子,更优选5至20个芳族环原子,其中至少一个为杂原子。杂原子优选选自N、O和/或S。本发明意义上的芳族或杂芳族环系旨在被认为是指如下体系,其不一定仅含芳基或杂芳基基团,而是其中多个芳基或杂芳基基团还可以通过非芳族单元(优选少于10%的除H以外的原子)连接,诸如sp3杂化的C、Si、N或O原子,sp2杂化的C或N原子或sp杂化的C原子。因此,例如,诸如9,9'-螺二芴、9,9'-二芳基芴、三芳基胺、二芳基醚和茋等的体系也旨在被认为是本发明意义上的芳族环系,其中两个或更多个芳基基团例如通过直链或环状的烷基、烯基或炔基基团或通过甲硅烷基基团连接的体系也是如此。此外,其中两个或更多个芳基或杂芳基基团通过单键彼此连接的体系,诸如联苯、三联苯或二苯基三嗪的体系,也被认为是本发明意义上的芳族或杂芳族环系。
在每种情况下还可以被上文定义的基团取代并且可以通过任何期望位置与芳族或杂芳族基团连接的具有5-60个芳族环原子的芳族或杂芳族环系,被认为特别指衍生自以下物质的基团:苯、萘、蒽、苯并蒽、菲、苯并菲、芘、苣、苝、荧蒽、并四苯、并五苯、苯并芘、联苯、联二苯叉、三联苯、联三苯叉、四联苯、芴、螺二芴、二氢菲、二氢芘、四氢芘、顺式或反式茚并芴、三聚茚、异三聚茚、螺三聚茚、螺异三聚茚、呋喃、苯并呋喃、异苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、异苯并噻吩、二苯并噻吩、吡咯、吲哚、异吲哚、咔唑、吲哚并咔唑、茚并咔唑、吡啶、喹啉、异喹啉、吖啶、菲啶、苯并-5,6-喹啉、苯并-6,7-喹啉、苯并-7,8-喹啉、吩噻嗪、吩嗪、吡唑、吲唑、咪唑、苯并咪唑、萘并咪唑、菲并咪唑、吡啶并咪唑、吡嗪并咪唑、喹喔啉并咪唑、唑、苯并唑、萘并唑、蒽并唑、菲并唑、异唑、1,2-噻唑、1,3-噻唑、苯并噻唑、哒嗪、苯并哒嗪、嘧啶、苯并嘧啶、喹喔啉、1,5-二氮杂蒽、2,7-二氮杂芘、2,3-二氮杂芘、1,6-二氮杂芘、1,8-二氮杂芘、4,5-二氮杂芘、4,5,9,10-四氮杂苝、吡嗪、吩嗪、吩嗪、吩噻嗪、荧红环、萘啶、氮杂咔唑、苯并咔啉、菲咯啉、1,2,3-***、1,2,4-***、苯并***、1,2,3-二唑、1,2,4-二唑、1,2,5-二唑、1,3,4-二唑、1,2,3-噻二唑、1,2,4-噻二唑、1,2,5-噻二唑、1,3,4-噻二唑、1,3,5-三嗪、1,2,4-三嗪、1,2,3-三嗪、四唑、1,2,4,5-四嗪、1,2,3,4-四嗪、1,2,3,5-四嗪、嘌呤、蝶啶、吲哚嗪和苯并噻二唑或这些基团的组合。
出于本发明的目的,其中个别H原子或CH2基团还可以被上文在基团定义中提及的基团取代的具有1至40个C原子的直链的烷基基团或具有3至40个C原子的支链或环状的烷基基团或具有2至40个C原子的烯基或炔基基团,优选被认为是指基团甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、2-甲基丁基、正戊基、仲戊基、环戊基、新戊基、正己基、环己基、新己基、正庚基、环庚基、正辛基、环辛基、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、环戊烯基、己烯基、环己烯基、庚烯基、环庚烯基、辛烯基、环辛烯基、乙炔基、丙炔基、丁炔基、戊炔基、己炔基或辛炔基。具有1至40个C原子的烷氧基或硫代烷基基团优选被认为是指甲氧基、三氟甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、正戊氧基、仲戊氧基、2-甲基丁氧基、正己氧基、环己氧基、正庚氧基、环庚氧基、正辛氧基、环辛氧基、2-乙基己氧基、五氟乙氧基、2,2,2-三氟乙氧基、甲基硫基、乙基硫基、正丙基硫基、异丙基硫基、正丁基硫基、异丁基硫基、仲丁基硫基、叔丁基硫基、正戊基硫基、仲戊基硫基、正己基硫基、环己基硫基、正庚基硫基、环庚基硫基、正辛基硫基、环辛基硫基、2-乙基己基硫基、三氟甲基硫基、五氟乙基硫基、2,2,2-三氟乙基硫基、乙烯基硫基、丙烯基硫基、丁烯基硫基、戊烯基硫基、环戊烯基硫基、己烯基硫基、环己烯基硫基、庚烯基硫基、环庚烯基硫基、辛烯基硫基、环辛烯基硫基、乙炔基硫基、丙炔基硫基、丁炔基硫基、戊炔基硫基、己炔基硫基、庚炔基硫基或辛炔基硫基。
出于本申请的目的,两个或更多个基团可以彼此形成环的术语旨在被认为特别指两个基团通过化学键彼此连接。此通过以下方案说明:
然而,此外,上文提及的术语还旨在被认为是指,在两个基团之一表示氢的情况下,第二个基团在氢原子所键合的位置处键合,从而形成环。此通过以下方案说明:
此外,出于本申请的目的,空穴传输材料可以为空穴传输材料(HTM)和/或空穴注入材料(HIM)。空穴注入材料简化或促进了空穴即正电荷从阳极向有机层中的转移。空穴传输材料能够传输空穴,即正电荷,所述空穴通常从阳极或相邻层例如空穴注入层注入。
这些材料经常通过前沿轨道的特性描述,下面将对这些特性进行更详细地描述。材料的分子轨道,特别地还是最高占据分子轨道(HOMO)和最低未占分子轨道(LUMO),其能级以及最低三重态T1或最低激发单重态S1的能量通过量子化学计算确定。为了计算不含金属的有机物质,首先使用理论的B3PW91/6-31G(d)水平(电荷=0;自旋多重性=1)进行几何结构优化。随后根据优化的几何结构进行能量计算。在本文中使用理论的B3PW91/6-31G(d)水平(电荷0,自旋单重态)。对于含有金属的化合物,通过理论的HF/LanL2MB水平(电荷=0;自旋多重性=1)进行几何结构优化。类似于上文针对有机物质所述的方法进行能量计算,其不同之处在于,LanL2DZ基组用于金属原子,而6-31G(d)基组用于配体。能量计算以哈特里单位给出HOMO能级HEh或LUMO能级LEh。参考循环伏安法测量值校准的以电子伏特计的HOMO和LUMO能级由此如下确定:
HOMO(eV)=((HEh*27.212)-0.9899)/1.1206
LUMO(eV)=((LEh*27.212)-2.0041)/1.385。
出于本申请的目的,这些值分别被认为是材料的HOMO和LUMO能级。
最低三重态T1被定义为具有最低能量的三重态的能量,该能量来自所述的量子化学计算。
最低激发单重态S1被定义为具有最低能量的激发单重态的能量,该能量来自所述的量子化学计算。
本文所述的方法与所使用的软件包无关,并且总给出相同结果。用于此目的的常用程序的实例是“Gaussian09W”(Gaussian公司)和Q-Chem 4.1(Q-Chem公司)。
通常,空穴注入材料的HOMO能级比阳极的能级负,即通常至少为-4.9eV。
空穴传输材料通常具有优选至少-5.0eV的高HOMO能级。根据电子器件的结构,还可以使用空穴传输材料作为空穴注入材料。
根据一个优选的实施方式,式(1)化合物选自下式(2)至(5)的化合物,
其中符号X1、X2、V、R1和R2具有与上文所定义相同的含义,并且其中标记n等于0、1、2或3。
根据一个非常优选的实施方式,式(1)化合物选自下式(2a)至(5a)的化合物,
其中符号X1、X2、V、R1和R2以及标记n具有与上文所定义相同的含义。
根据一个特别优选的实施方式,式(1)化合物选自式(2b-1)至(5b-3)的化合物,
其中符号X1、X2和R2具有与上文所定义相同的含义。
基团R2在每次出现时相同或不同地表示-C(=O)Ar1、-P(=O)(Ar1)2、-S(=O)Ar1、-S(=O)2Ar1、-SAr1、-B(Ar1)2或-P(Ar1)2,优选-P(=O)(Ar1)2、-S(=O)Ar1和-S(=O)2Ar1。
基团Ar1在每次出现时优选相同或不同地为选自苯、萘、蒽、联苯、三联苯、芴、呋喃、苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、二苯并噻吩、咔唑、吲哚并咔唑、茚并咔唑或吡啶的芳族或杂芳族环系,这些基团中的每一个可以在任何自由位置处被一个或多个基团R4取代。更优选地,基团Ar1在每次出现时相同或不同地选自苯、萘、蒽、联苯、三联苯、芴,这些基团中的每一个可以在任何自由位置处被一个或多个基团R4取代。
此外,特别优选地,基团Ar1被至少一个氟原子或至少一个具有1至20个C原子的直链的氟代烷基基团或具有3至20个C原子的支链或环状的氟代烷基基团取代。
根据一个优选的实施方式,基团X1和X2在每次出现时相同或不同地选自如上文所定义的式(X-1)、(X-2)或(X-9)的基团。
根据一个非常优选的实施方式,基团X1表示式(X-1)基团,并且基团X2表示式(X-9)基团,或基团X1表示式(X-9)基团,并且基团X2表示式(X-1)基团。
根据另一个非常优选的实施方式,基团X1和X2在每次出现时相同或不同地选自如上文所定义的式(X-1)或(X-2)、优选(X-1)的基团。
以下化合物为式(1)化合物的实例:
式(1)化合物可以通过有机化学的已知方法或反应步骤制备。
用于制备式(1)化合物的优选方法如下方案1所示。
方案1
R为基团
R2具有与上文相同的定义
Y1、Y2为离去基团如卤素
可以从实施例获得关于上文示意性指示的方法和其他可能方法的细节。
必要时,本领域技术人员将能够偏离上文示意性指示的方法或对其进行修改,以获得式(1)化合物。这在本领域技术人员的常见能力范围内进行。
上述根据本发明的化合物,特别是用反应性离去基团,诸如溴、碘、氯、硼酸或硼酸酯取代的化合物,可以用作用于制备相应低聚物、树枝状大分子或聚合物的单体。合适的反应性离去基团为例如溴、碘、氯、硼酸、硼酸酯、胺、分别含有末端C-C双键或三键的烯基或炔基基团、环氧乙烷、氧杂环丁烷、经历环加成例如1,3-偶极环加成的基团诸如二烯或叠氮化物、羧酸衍生物、醇和硅烷。
因此,本发明还涉及包含一种或多种式(1)化合物的低聚物、聚合物或树枝状大分子,其中与聚合物、低聚物或树枝状大分子连接的键可以位于式(1)中被R、R1或R2取代的任何期望位置处。根据式(1)的化合物的连接,所述化合物为低聚物或聚合物的侧链的一部分或主链的一部分。
本发明意义上的低聚物被认为是指由至少三个单体单元构成的化合物。本发明意义上的聚合物被认为是指由至少十个单体单元构成的化合物。根据本发明的聚合物、低聚物或树枝状大分子可以是共轭的、部分共轭的或非共轭的。根据本发明的低聚物或聚合物可以为线性、支化或树枝状的。在以线性方式连接的结构中,式(1)的单元可以彼此直接连接,或通过二价基团,例如通过取代或未取代的烷亚基基团,通过杂原子或通过二价芳族或杂芳族基团彼此连接。在支化和树枝状结构中,例如,三个或更多个式(1)的单元可以通过三价或多价基团,例如通过三价或多价芳族或杂芳族基团连接,以得到支化或树枝状的低聚物或聚合物。
与上文对于式(1)化合物所述相同的优选方式适用于低聚物、树枝状大分子和聚合物中的式(1)的重复单元。
为了制备低聚物或聚合物,使根据本发明的单体均聚或与其他单体共聚。适合且优选的共聚单体选自芴(例如根据EP 842208或WO 00/22026)、螺二芴(例如根据EP707020、EP 894107或WO 06/061181)、对苯亚基(例如根据WO 1992/18552)、咔唑(例如根据WO 04/070772或WO 2004/113468)、噻吩(例如根据EP 1028136)、二氢菲(例如根据WO2005/014689或WO 2007/006383)、顺式和反式茚并芴(例如根据WO 2004/041901或WO2004/113412)、酮(例如根据WO 2005/040302)、菲(例如根据WO 2005/104264或WO 2007/017066)或者多种这些单元。所述聚合物、低聚物和树枝状大分子通常还含有其他单元,例如发光(荧光或磷光)单元,诸如乙烯基三芳基胺(例如根据WO 2007/068325)或磷光金属络合物(例如根据WO 2006/003000),和/或电荷传输单元,特别是基于三芳基胺的那些电荷传输单元。
根据本发明的聚合物、低聚物和树枝状大分子具有有利的特性,特别是长寿命、高效率和良好的色坐标。
通常通过使一种或多种类型的单体聚合来制备根据本发明的聚合物和低聚物,所述单体中的至少一种单体产生聚合物中的式(1)的重复单元。合适的聚合反应为本领域技术人员所已知并且描述在文献中。产生C-C或C-N连接的特别合适且优选的聚合反应如下:
(A)SUZUKI聚合;
(B)YAMAMOTO聚合;
(C)STILLE聚合;和
(D)HARTWIG-BUCHWALD聚合。
可以通过这些方法进行聚合的方式以及然后可以将聚合物从反应介质中分离出并纯化的方式,是本领域技术人员已知的并且详细描述在文献中,例如WO 2003/048225、WO2004/037887和WO 2004/037887中。
为了从液相例如通过旋涂或通过印刷方法处理根据本发明的化合物,需要根据本发明的化合物的制剂。这些制剂可以为例如溶液、分散液或乳液。出于此目的,优选可以使用两种或更多种溶剂的混合物。合适且优选的溶剂为例如甲苯;苯甲醚;邻-、间-或对-二甲苯;苯甲酸甲酯;1,3,5-三甲基苯;四氢萘;藜芦醚;THF;甲基-THF;THP;氯苯;二烷;苯氧基甲苯,特别是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-甲基苯并噻唑;2-苯氧基乙醇;2-吡咯烷酮;3-甲基苯甲醚;4-甲基苯甲醚;3,4-二甲基苯甲醚;3,5-二甲基苯甲醚;苯乙酮;α甲萜品醇;苯并噻唑;苯甲酸丁酯;异丙苯;环己醇;环己酮;环己基苯;十氢萘;十二烷基苯;苯甲酸乙酯;茚满;苯甲酸甲酯;NMP;对伞花烃;苯***;1,4-二异丙基苯;二苄醚;二乙二醇丁甲醚;三乙二醇丁甲醚;二乙二醇二丁醚;三乙二醇二甲醚;二乙二醇单丁醚;三丙二醇二甲醚;四乙二醇二甲醚;2-异丙基萘;戊基苯;己基苯;庚基苯;辛基苯;1,1-双(3,4-二甲基苯基)乙烷;或这些溶剂的混合物。
因此,本发明还涉及一种制剂,特别是溶液、分散液或乳液,其包含至少一种式(1)化合物或含有至少一种式(1)单元的至少一种聚合物、低聚物或树枝状大分子,以及至少一种溶剂,优选有机溶剂。可以制备此类溶液的方式是本领域技术人员所已知的,并且例如在WO 2002/072714、WO 2003/019694及其中引用的文献中进行了描述。
式(1)化合物适用于电子器件、特别是有机电致发光器件(OLED)。根据取代,将化合物用于不同的功能和层中。
式(1)化合物可以用于有机电致发光器件中的任何功能,例如用作空穴注入材料、p型掺杂剂、空穴传输性材料,用作基质材料,用作发光材料或用作电子传输性材料。
因此,本发明还涉及式(1)化合物在电子器件中的用途。本文的电子器件优选选自有机集成电路(OIC)、有机场效应晶体管(OFET)、有机薄膜晶体管(OTFT)、有机发光晶体管(OLET)、有机太阳能电池(OSC)、有机光学检测器、有机光感受器、有机场猝熄器件(OFQD)、有机发光电化学电池(OLEC)、有机激光二极管(O-laser),并且特别优选有机电致发光器件(OLED)。
本发明还涉及包含至少一种式(1)化合物的电子器件。电子器件优选选自上述器件。特别优选包含阳极、阴极和至少一个发光层的有机电致发光器件,其特征在于至少一个有机层包含至少一种式(1)化合物。
除阴极、阳极和发光层以外,有机电致发光器件还可以包含其他层。在每种情况下,这些其他层例如选自一个或多个空穴注入层、空穴传输层、空穴阻挡层、电子传输层、电子注入层、电子阻挡层、激子阻挡层、中间层、电荷产生层(IDMC 2003,中国台湾;Session21OLED(5),T.Matsumoto,T.Nakada,J.Endo,K.Mori,N.Kawamura,A.Yokoi,J.Kido,具有电荷产生层的多光子有机EL器件(Multiphoton Organic EL Device Having ChargeGeneration Layer))和/或有机或无机p/n结。
有机电致发光器件的层的次序优选如下:阳极-空穴注入层-空穴传输层-发光层-电子传输层-电子注入层-阴极。不必存在所有的所述层,并且可以另外存在其他层,例如在阳极侧与发光层相邻的电子阻挡层或在阴极侧与发光层相邻的空穴阻挡层。
根据本申请的空穴传输层为具有空穴传输性功能的层,该层存在于阳极与发光层之间。特别地,它为不是空穴注入层或电子阻挡层的空穴传输性层。本申请意义上的空穴注入层和电子阻挡层应理解为是空穴传输性层的特定实施方式。在阳极与发光层之间具有多个空穴传输性层的情况下,空穴注入层为与阳极相邻或与阳极仅间隔有单个涂层的空穴传输性层。在阳极与发光层之间具有多个空穴传输性层的情况下,电子阻挡层为在阳极侧与发光层相邻的空穴传输性层。
根据本发明的有机电致发光器件可以包含多个发光层。在此情况下,这些发光层特别优选在380nm至750nm之间总共具有多个发光峰值,使得总体上产生白色发光,即将能够发荧光或发磷光以及发蓝光、绿光、黄光、橙光或红光的多种发光化合物用于发光层中。特别优选为三层体系,即具有三个发光层的体系,其中这些层中的至少一个优选包含至少一种式(1)化合物,并且其中该三个层表现出蓝色、绿色、黄色、橙色或红色发光(对于基本结构,参见例如WO 2005/011013)。应注意,为了产生白光,代替在颜色中发光的多种发光体化合物,单独使用的在宽波长范围内发光的发光体化合物也可以是合适的。替代地和/或另外地,根据本发明的化合物还可以存在于空穴传输层中或此类有机电致发光器件中的另一个层中。多种发光层可以直接彼此相邻,或它们可以彼此间隔有非发光层。根据本发明的一个优选实施方式,白色发光OLED为所谓的串联OLED,即在OLED中存在两个或更多个完整的OLED层序列,其中在每种情况下OLED层序列包含空穴传输层、发光层和电子传输层,这些层各自彼此间隔有电荷产生层。
根据一个优选的实施方式,式(1)化合物作为p型掺杂剂与一种或多种空穴传输材料组合用于空穴传输性层(例如空穴注入层、空穴传输层或电子阻挡层)中。可以与式(1)化合物组合用于空穴传输、空穴注入或电子阻挡层中的优选空穴传输材料为茚并芴胺衍生物(例如根据WO 06/122630或WO 06/100896)、EP 1661888中公开的胺衍生物、六氮杂联三苯叉衍生物(例如根据WO 01/049806)、含有稠合芳族环的胺衍生物(例如根据US 5,061,569)、WO 95/09147中公开的胺衍生物、单苯并茚并芴胺(例如根据WO 08/006449)、二苯并茚并芴胺(例如根据WO 07/140847)、螺二芴胺(例如根据WO 2012/034627或WO 2013/120577)、芴胺(例如根据EP 2875092、EP 2875699和EP 2875004)、螺二苯并吡喃胺(例如根据WO 2013/083216)和二氢吖啶衍生物(例如根据WO 2012/150001)。
当式(1)化合物用作空穴传输性层中的p型掺杂剂时,式(1)化合物在空穴传输性层的混合物中的比例为0.1至50.0%、优选0.5至20.0%、特别优选1.0至10.0%。相应地,空穴传输材料的比例为50.0至99.9%、优选80.0至99.5%、特别优选90.0至99.0%。
出于本申请的目的,如果从气相施加化合物时,以%表示的比例的规格被认为是指体积%,并且如果从溶液施加化合物时,所述规格被认为是指重量%。
p型掺杂剂优选在p型掺杂层中基本上均匀分布。这可以例如通过p型掺杂剂和空穴传输材料基质的共蒸发来实现。
用作层中的p型掺杂剂的式(1)化合物可以与其他p型掺杂剂组合使用。
除式(1)化合物以外的p型掺杂剂的特别优选实施方式为WO 2011/073149、EP1968131、EP 2276085、EP 2213662、EP 1722602、EP 2045848、DE 102007031220、US8044390、US 8057712、WO 2009/003455、WO 2010/094378、WO 2011/120709、US 2010/0096600、WO 2012/095143和DE 102012209523中公开的化合物。
除式(1)化合物以外的特别优选p型掺杂剂为醌二甲烷化合物;氮杂茚并芴二酮;氮杂莒;氮杂联三苯叉;I2;金属卤化物,优选过渡金属卤化物;金属氧化物,优选含有至少一种过渡金属或第3主族金属的金属氧化物;和过渡金属络合物,优选Cu、Co、Ni、Pd和Pt与含有至少一个氧原子作为键合位点的配体的络合物。还优选过渡金属氧化物作为掺杂剂,优选铼、钼和钨的氧化物,特别优选Re2O7、MoO3、WO3和ReO3。
除式(1)化合物以外的合适p型掺杂剂的实例为化合物(D-1)至(D-13):
根据另一个优选的实施方式,式(1)化合物可以用作例如空穴传输层、空穴注入层或电子阻挡层中的主要化合物,其以纯材料的形式,即以100%的比例使用,或它可以与一种或多种其他化合物组合使用。当它与一种或多种其他化合物组合使用时,则式(1)化合物的比例优选为50.0至99.9%、优选80.0至99.5%、特别优选90.0至99.0%。
当式(1)化合物用作空穴注入层中的主要化合物(比例为50至100%、优选80至100%、非常优选90至100%、特别优选99至100%)时,则该空穴注入层的层厚度为0.5至50nm、优选1至20nm、非常优选1至10nm并且特别优选1至5nm。
电子器件还优选在阳极与发光层之间具有多个空穴传输性层。可以发生以下情况:所有这些层均包含式(1)化合物,或仅其单个层包含式(1)化合物。
下文指示了在根据本发明的有机电致发光器件中用作相应功能材料的通常优选的材料类别。
合适的磷光发光化合物特别是以下化合物,其在合适的激发下优选在可见光区域发光,并且另外含有至少一个原子序数大于20、优选大于38并且小于84、特别优选大于56并且小于80的原子。使用的磷光发光化合物优选为含有铜、钼、钨、铼、钌、锇、铑、铱、钯、铂、银、金或铕的化合物,特别是含有铱、铂或铜的化合物。
在本发明的意义上,所有发光的铱、铂或铜络合物均被认为是磷光化合物。
上述磷光发光体的实例通过如下申请揭示:WO 00/70655、WO 2001/41512、WO2002/02714、WO 2002/15645、EP 1191613、EP 1191612、EP 1191614、WO 05/033244、WO 05/019373、US 2005/0258742、WO 2009/146770、WO 2010/015307、WO 2010/031485、WO 2010/054731、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、WO 2014/094960或WO 2016/124304。通常,根据现有技术用于磷光OLED并且为有机电致发光领域的技术人员已知的所有磷光络合物均为合适的,并且本领域技术人员将能够不付出创造性劳动而使用其他磷光络合物。
除了根据本发明的化合物之外,优选的荧光发光体选自芳基胺类。本发明意义上的芳基胺被认为是指含有直接与氮键合的三个取代或未取代的芳族或杂芳族环系的化合物。这些芳族或杂芳族环系中的至少一个优选为稠合环系,特别优选具有至少14个芳族环原子的稠合环系。其优选实例为芳族蒽胺、芳族蒽二胺、芳族芘胺、芳族芘二胺、芳族苣胺或芳族苣二胺。芳族蒽胺被认为是指如下化合物,其中一个二芳基氨基基团直接与蒽基团键合,优选在9位键合。芳族蒽二胺被认为是指如下化合物,其中两个二芳基氨基基团直接与蒽基团键合,优选在9,10位键合。芳族的芘胺、芘二胺、苣胺和苣二胺与此类似地定义,其中二芳基氨基基团与芘优选在1位或1,6位键合。其他优选的发光体为茚并芴胺或茚并芴二胺,例如根据WO 2006/108497或WO 2006/122630;苯并茚并芴胺或苯并茚并芴二胺,例如根据WO 2008/006449;和二苯并茚并芴胺或二苯并茚并芴二胺,例如根据WO 2007/140847;以及WO 2010/012328中公开的含有稠合芳基基团的茚并芴衍生物。同样优选为WO 2012/048780和WO 2013/185871中公开的芘芳基胺。同样优选为WO 2014/037077中公开的苯并茚并芴胺、WO 2014/106522中公开的苯并芴胺、WO 2014/111269和WO 2017/036574中公开的苯并茚并芴、WO 2017/028940和WO 2017/028941中公开的吩嗪和WO 2016/150544中公开的芴衍生物。
用于与荧光发光化合物组合使用的优选基质材料选自以下的类别:低聚芳亚基(例如根据EP 676461的2,2',7,7'-四苯基螺二芴,或二萘基蒽),特别是含有稠合的芳族基团的低聚芳亚基;低聚芳亚基乙烯亚基(例如根据EP 676461的DPVBi或螺-DPVBi);多足金属络合物(例如根据WO 2004/081017);空穴传导化合物(例如根据WO 2004/058911);电子传导化合物,特别是酮、氧化膦、亚砜等(例如根据WO 2005/084081和WO 2005/084082);阻转异构体(例如根据WO 2006/048268);硼酸衍生物(例如根据WO 2006/117052)或苯并蒽(例如根据WO 2008/145239)。特别优选的基质材料选自以下的类别:低聚芳亚基,其包含萘、蒽、苯并蒽和/或芘或这些化合物的阻转异构体;低聚芳亚基乙烯亚基;酮;氧化膦;和亚砜。非常特别优选的基质材料选自包含蒽、苯并蒽、苯并菲和/或芘或这些化合物的阻转异构体的低聚芳亚基的类别。本发明意义上的低聚芳亚基旨在被认为是指至少三个芳基或芳亚基基团彼此键合的化合物。还优选WO 2006/097208、WO 2006/131192、WO 2007/065550、WO 2007/110129、WO 2007/065678、WO 2008/145239、WO 2009/100925、WO 2011/054442和EP 1553154中公开的蒽衍生物,EP 1749809、EP 1905754和US 2012/0187826中公开的芘化合物,WO 2015/158409中公开的苯并蒽基-蒽衍生物,WO 2017/025165中公开的茚并苯并呋喃以及WO 2017/036573中公开的菲基-蒽。
用于与磷光发光组合使用的优选基质材料为芳族酮、芳族氧化膦或芳族亚砜或砜,例如根据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-双咔唑基联苯)或WO 2005/039246、US 2005/0069729、JP2004/288381、EP 1205527或WO 2008/086851中公开的咔唑衍生物;吲哚并咔唑衍生物,例如根据WO 2007/063754或WO 2008/056746;茚并咔唑衍生物,例如根据WO 2010/136109、WO2011/000455或WO 2013/041176;氮杂咔唑衍生物,例如根据EP 1617710、EP 1617711、EP1731584、JP 2005/347160;双极性基质材料,例如根据WO 2007/137725;硅烷,例如根据WO2005/111172;硼氮杂环戊熳或硼酸酯,例如根据WO 2006/117052;三嗪衍生物,例如根据WO2010/015306、WO 2007/063754或WO 2008/056746;锌络合物,例如根据EP 652273或WO2009/062578;硅二氮杂环戊熳衍生物或硅四氮杂环戊熳衍生物,例如根据WO 2010/054729;磷二氮杂环戊熳衍生物,例如根据WO 2010/054730;桥连的咔唑衍生物,例如根据US 2009/0136779、WO 2010/050778、WO 2011/042107、WO 2011/088877或WO 2012/143080;联三苯叉衍生物,例如根据WO 2012/048781;或内酰胺,例如根据WO 2011/116865或WO2011/137951。
可用于根据本发明的有机电致发光器件的空穴注入或空穴传输层或电子阻挡层中或电子传输层中的合适电荷传输材料为例如Y.Shirota等人,化学评论(Chem.Rev.)2007,107(4),953-1010中公开的化合物,或根据现有技术用于这些层中的其他材料。
可以用于根据本发明的电致发光器件中的空穴传输、空穴注入或电子阻挡层中的优选空穴传输材料的实例为,茚并芴胺衍生物(例如根据WO 06/122630或WO 06/100896);EP 1661888中公开的胺衍生物;六氮杂联三苯叉衍生物(例如根据WO 01/049806);含有稠合芳族环的胺衍生物(例如根据US 5,061,569);WO 95/09147中公开的胺衍生物;单苯并茚并芴胺(例如根据WO 08/006449);二苯并茚并芴胺(例如根据WO 07/140847);螺二芴胺(例如根据WO 2012/034627或WO 2013/120577);芴胺(例如根据WO 2014/015937、WO 2014/015938、WO 2014/015935和WO 2015/082/056);螺二苯并吡喃胺(例如根据WO 2013/083216);二氢吖啶衍生物(例如根据WO 2012/150001);螺二苯并呋喃和螺二苯并噻吩,例如根据WO 2015/022051和WO 2016/102048和WO 2016/131521;菲二芳基胺,例如根据WO2015/131976;螺三苯并环庚三烯酚酮,例如根据WO 2016/087017;具有间-苯基二胺基团的螺二芴,例如根据WO 2016/078738;螺双吖啶,例如根据WO 2015/158411;氧杂蒽二芳基胺,例如根据WO 2014/072017;以及根据WO2015/086108的具有二芳基氨基基团的9,10-二氢蒽螺环化合物。
关于电子传输层,根据现有技术已知或用作电子传输材料的材料均可以用于电子传输层中。特别合适作为电子传输材料的是以下化合物:铝络合物,例如Alq3;锆络合物,例如Zrq4;锂络合物,例如Liq;苯并咪唑衍生物;三嗪衍生物;嘧啶衍生物;吡啶衍生物;吡嗪衍生物;喹喔啉衍生物;喹啉衍生物;二唑衍生物;芳族酮;内酰胺;硼烷;磷二氮杂环戊熳衍生物和氧化膦衍生物。其他合适的材料为如JP 2000/053957、WO 2003/060956、WO 2004/028217、WO 2004/080975和WO 2010/072300中所述的以上化合物的衍生物。
有机电致发光器件的阴极优选包含具有低逸出功的金属、金属合金或多层结构,所述金属合金或多层结构包含多种金属,诸如碱土金属、碱金属、主族金属或镧系元素(例如Ca、Ba、Mg、Al、In、Mg、Yb、Sm等)。也合适的是包含碱金属或碱土金属和银的合金,例如包含镁和银的合金。在多层结构的情况下,除了所述金属以外,还可以使用具有相对高逸出功的其他金属,诸如Ag或Al,在该情况下,通常使用金属的组合,诸如Ca/Ag、Mg/Ag或Ag/Ag。还可以优选在金属阴极与有机半导体之间引入具有高介电常数的材料的薄中间层。适用于此目的的是例如碱金属氟化物或碱土金属氟化物,以及相应的氧化物或碳酸盐(例如LiF、Li2O、BaF2、MgO、NaF、CsF、Cs2CO3等)。此外,可以将喹啉锂(LiQ)用于此目的。此层的层厚度优选为0.5nm至5nm。
阳极优选包含具有高逸出功的材料。优选地,阳极的逸出功为相较于真空大于4.5eV。一方面,适用于此目的的为具有高氧化还原电位的金属,诸如Ag、Pt或Au。另一方面,金属/金属氧化物电极(例如Al/Ni/NiOx、Al/PtOx)也可以是优选的。对于一些应用,所述电极中的至少一个必须是透明或半透明的,以促进有机材料的照射(有机太阳能电池)或光的耦合输出(OLED、O-laser)。本文的优选阳极材料为导电性混合金属氧化物。特别优选为氧化锡铟(ITO)或氧化铟锌(IZO)。此外,优选为导电性掺杂有机材料,特别是导电性掺杂聚合物。
将该器件适当地(根据本申请)结构化,使其具有接触点并最终密封,因为根据本发明的器件的寿命在存在水和/或空气下会缩短。
在一个优选的实施方式中,根据本发明的有机电致发光器件的特征在于,通过升华方法涂布一个或多个层,其中,通过在真空升华单元中以小于10-5毫巴、优选小于10-6毫巴的初始压力进行气相沉积来施加材料。然而,在本文中,初始压力还可以甚至更低,例如小于10-7毫巴。
还优选如下有机电致发光器件,其特征在于通过OVPD(有机气相沉积)方法或通过载气升华来涂布一个或多个层,其中在10-5毫巴至1巴的压力下施加材料。此方法的一个特殊情况为OVJP(有机蒸气喷印)法,其中这些材料通过喷嘴直接施加并因此结构化(例如M.S.Arnold等人,应用物理快报(Appl.Phys.Lett.)2008,92,053301)。
此外优选为如下有机电致发光器件,其特征在于诸如通过旋涂或通过任何期望印刷方法,诸如丝网印刷、柔版印刷、喷嘴印刷或胶版印刷,但特别优选LITI(光诱导的热成像、热转移印刷)或喷墨印刷,从溶液产生一个或多个层。可溶的式(1)化合物是此目的所必需的。高溶解性可以通过合适地取代这些化合物实现。
为了生产根据本发明的有机电致发光器件,还优选从溶液施加一个或多个层以及通过升华方法施加一个或多个层。
根据本发明,包含一种或多种根据本发明的化合物的电子器件可以用于显示器中,用作照明应用中的光源以及用作医学和/或美容应用(例如光疗法)中的光源。
实施例
A)合成例
实施例1
3,9-双(苯基磺酰基)-6,12-双(二氰基甲亚基)茚并[1,2-b]芴
a)4,4”-二溴-[1,1';4',1”]三联苯-2,2”-二甲酸二甲酯
在惰性氛围下,将1,3-苯亚基二硼酸(17.04g,102.8mmol)、5-溴-2-碘-苯甲酸甲酯(77.1g,226.2mmol)、Pd(PPh3)4(11.9g,10.3mmol)和K2CO3(55.8g,411.2mmol)溶解在甲苯(700ml)、乙醇(400ml)和水(250ml)中。将反应物脱气并加热至70℃后维持四天。停止反应并冷却后,将反应混合物倒入水(600ml)中,剧烈搅拌,最后分离各层。用乙酸乙酯(2×200ml)萃取水层。用盐水(150ml)洗涤合并的有机层并用MgSO4干燥。在真空中浓缩产物,并且得到呈黄色液体状的粗产物。通过快速硅胶色谱法,用庚烷和二氯甲烷(分别为1:2)作为洗脱剂来纯化混合物。得到呈白色固体状的产物(31.4g,62.3mmol,61%)。
LC-APLI-MS(100Hz,正):92.1%,m/z=501.9(M+)
b)4,4”-双(苯基磺酰基)-[1,1':4',1”-三联苯]-2,2”-二甲酸二甲酯
在氩气下,将4,4”-二溴-[1,1';4',1”]三联苯-2,2”-二甲酸二甲酯(25g,49.6mmol)、苯亚磺酸钠(17.9g,109.1mmol)、4,5-双(二苯基膦)-9,9-二甲基氧杂蒽(1.43g,2.48mmol)、Pd2(dba)3(1.36g,1.49mmol)、CsCO3(24.2g,74.4mmol)和Bu4NCl*H2O(16.5g,59.5mmol)溶解在甲苯(1L)中。将溶液脱气,随后加热至105℃后维持三天。冷却至室温后,将反应混合物倒入水(300ml)中,剧烈搅拌,最后分离各层。用DCM(2×200ml)萃取水层。浓缩合并的有机层,并使粗产物从庚烷、DCM和甲苯中重结晶。得到呈亮黄色固体状的产物(19.1g,30.5mmol,62%)。
APCI-MS(负)m/z=626.3(M-)
FT-IR(ATR)=1726cm-1(-O-C=O-),1242cm-1(-O-C=O-)
c)3,9-双(苯基磺酰基)茚并[1,2-b]芴-6,12-二酮
将4,4”-双(苯基磺酰基)-[1,1':4',1”-三联苯]-2,2”-二甲酸二甲酯(15.3g,24.4mmol)溶解在浓H2SO4(500ml)中。将混合物加热至75℃后过夜,并且溶液颜色为深红色。通过FT-IR(ATR)测量跟踪反应进程。当反应停止时,将其冷却至室温,然后将反应混合物缓慢倒入冰水中。滤出精细固体,用大量水和二氯甲烷洗涤,并在60℃下在真空中干燥。得到呈深褐色固体状的产物(9.37g,16.7mmol,68%)。
MALDI-TOF-MS(DHB,100Hz,负)=562(100%,M-)
FT-IR(ATR)=1716cm-1(C=O)
d)3,9-双(苯基磺酰基)-6,12-双(二氰基甲亚基)茚并[1,2-b]芴
将3,9-双(苯基磺酰基)茚并[1,2-b]芴-6,12-二酮(250mg,0.44mmol)与丙二腈(191mg,2.9mmol)一起溶解在吡啶(5ml)和甲苯(20ml)中。将混合物加热至180℃后过夜。反应完成后,将其浓缩并用庚烷和二氯甲烷洗涤剩余晶体。得到呈深褐色固体状的产物(143mg,0.22mmol,49%)。将其通过升华进一步纯化。
MALDI-TOF-MS(DHB,100Hz,负)=658(M-),696([M--H+K]-)
FT-IR(ATR)=2209cm-1(CN)
实施例2
2,8-双(苯基磺酰基)-10,12-双(二氰基甲亚基)茚并[2,1-b]芴
a)2-溴-5-(苯基磺酰基)苯甲酸甲酯
反应类似于化学用化学催化剂(Chem.Cat.Chem.)2015,7,1539-1542进行。催化剂的制备:在氩气下,将Cu(I)Br(2.00g,14mmol)和1,10-菲咯啉(2.51g,14mmol)溶解在二氯甲烷(70ml)中。在室温下持续搅拌2h。在真空中去除溶剂,并且得到呈固体状的催化剂phenCu(I)Br,并将其直接用于下一反应中。
在环境条件下,将2-溴-5-(氯磺酰基)苯甲酸甲酯(40g,128mmol)、苯基硼酸(18.7g,153mmol)、K2CO3(35.3g,255mmol)和phenCu(I)Br(4.44g,14mmol)溶解在二氯甲烷(1.6l)和水(20ml)中。在室温下持续搅拌三天。然后将反应混合物倒入水(500ml)中并分离各层。用二氯甲烷(3×100ml)萃取水层。用盐水(100ml)洗涤合并的有机层并用MgSO4干燥。在真空中去除溶剂并通过硅胶柱色谱法用二氯甲烷/庚烷(2:1)作为洗脱剂来纯化粗产物(35.7g)。得到呈白色固体状的产物(19.0g,53.3mmol,42%)。
GC-MS(EI,70eV)=356/354(60%),325/323(70%),263/261(30%),125(100%),77(70%)
b)4,4”-双(苯基磺酰基)-[1,1':3',1”-三联苯]-2,2”-二甲酸二甲酯
在氩气下,将2-溴-5-(苯基磺酰基)苯甲酸甲酯(17.6g,49.5mmol)、1,3-苯亚基二硼酸(3.91g,23.6mmol)、K3PO4(20.0g,94.4mmol)和Pd(PPh3)4(2.18g,1.9mmol)溶解在甲苯(700ml)、乙醇(400ml)和水(300ml)中。将溶液脱气,随后加热至65℃后维持两天。冷却至室温后,将反应混合物倒入水(200ml)中。分离各层,并用甲苯(3×100ml)萃取水层。用盐水洗涤合并的有机层并用MgSO4干燥。在真空中去除溶剂,并且得到呈胶样材料状的粗产物。使用硅胶柱色谱法用庚烷和乙酸乙酯作为洗脱剂来进一步纯化。得到呈黄色固体状的产物(9.35g,14.9mmol,63%)。
GC-MS(EI,70eV)=626(50%,M+),563(100%)
FT-IR(ATR,纯)=1728cm-1(C=O)
c)2,8-双(苯基磺酰基)茚并[2,1-b]芴-10,12-二酮
将4,4”-双(苯基磺酰基)-[1,1':3',1”-三联苯]-2,2”-二甲酸二甲酯(8.5g,13.6mmol)和浓硫酸(170ml)在搅拌下加热至90℃后维持两天。将反应混合物冷却至室温,并倒入冰水中。通过过滤收集黄色沉淀物并用水和庚烷洗涤。在真空中干燥并收集呈黄色固体状的粗产物。通过硅胶柱色谱法用庚烷和乙酸乙酯纯化粗产物。
MALDI-MS(DHB,100Hz,正)=562(100%,M-)
FT-IR(ATR,纯)=1704,1720cm-1(C=O)
d)2,8-双(苯基磺酰基)-10,12-双(二氰基甲亚基)茚并[2,1-b]芴
将粗2,8-双(苯基磺酰基)茚并[2,1-b]芴-10,12-二酮(7.2g,12.8mmol)和丙二腈(5.1g,76.8mmol)溶解在吡啶(200ml)中。将反应混合物加热至65℃后维持5h。冷却至室温后,滤出沉淀物。用水、庚烷和二氯甲烷洗涤粗产物并在真空中干燥。得到呈橙色粉末状的粗产物。将其通过升华进一步纯化。
MALDI-MS(DHB,100Hz,负)=658(100%,M+)
FT-IR(ATR,纯)=2224cm-1(CN)
实施例3
(2,9-双(苯基磺酰基)-7-(二氰基甲亚基))茚并[1,2-a]芴-12-酮
a)2,9-双(苯基磺酰基)茚并[1,2-a]芴-7,12-二酮
将4,4”-双(苯基磺酰基)-[1,1':3',1”-三联苯]-2,2”-二甲酸二甲酯(8.5g,13.6mmol)和浓硫酸(170ml)在搅拌下加热至90℃后维持两天。将反应混合物冷却至室温,并倒入冰水中。通过过滤收集黄色沉淀物并用水和庚烷洗涤。在真空中干燥并收集呈黄色固体状的粗产物。通过硅胶柱色谱法用庚烷和乙酸乙酯纯化粗产物。
MALDI-MS(DHB,100Hz,正)=562(100%,M+)
FT-IR(ATR,纯)=1714cm-1(C=O)
b)(2,9-双(苯基磺酰基)-7-(二氰基甲亚基))茚并[1,2-a]芴-12-酮
将粗2,8-双(苯基磺酰基)茚并[2,1-b]芴-10,12-二酮(7.2g,12.8mmol)和丙二腈(5.1g,76.8mmol)溶解在吡啶(200ml)中。将反应混合物加热至65℃后维持5h。冷却至室温后,滤出沉淀物。用水、庚烷和二氯甲烷洗涤粗产物并在真空中干燥。得到呈橙色粉末状的粗产物。将其通过升华进一步纯化。
MALDI-MS(DHB,100Hz,负)=610(100%,M+)
FT-IR(ATR,纯)=2224cm-1(CN),1711cm-1(C=O)
B)OLED的制造
基底预处理:所用基底为涂有厚度为50nm的结构化ITO(氧化锡铟)的玻璃板。
将新清洁的基底转移到蒸发工具中。在本文中,将基底用氧等离子体预处理130s,之后用氩等离子体处理150s(氧氩),或仅用氧等离子体预处理130s(氧)。
之后,通过物理气相沉积来沉积多个有机层。
通过参比实验确定层的厚度,其中沉积约100nm有机材料的厚层。在蒸发期间用基于石英晶体微量天平的薄膜厚度监测器(例如Inficon)测量厚度。通过在顶部蒸发薄铝膜来保护该有机层。然后,通过表面轮廓仪(例如K-LA-Tencor P7)测量有机层的实际厚度。薄膜监测器的加工因子以使表面轮廓仪与薄膜监测器的膜厚度相同的方式进行调整。
这些器件基本上具有以下层结构:基底/空穴注入层(HIL)/空穴传输层(HTL),最后为阴极,或:基底/HTM:HIM(X%)/空穴传输层(HTL),并且最后为阴极。阴极由厚度为100nm的铝层形成。
所有材料均通过在真空室中进行热气相沉积来施加。本文的诸如HTM:HIM(X%)的表达是指材料HTM在该层中以体积比例(100-X)%存在,并且HIM在该层中以X%的比例存在。
本发明化合物作为仅空穴器件中的HIL材料的用途:
所述器件为仅空穴器件,其中实施例1、2和3的本发明化合物被用于HIL中。可以显示,与没有HIL的器件相比,可以用由本发明化合物制成的HIL来获得降低的电压。
Claims (16)
1.一种式(1)的化合物,
其中以下适用于所用符号和标记:
W为CR1、CR2或N;
V为CR、N,并且至少两个相邻的基团V表示式(V-1)的基团,
X1、X2在每次出现时相同或不同地选自式(X-1)至(X-9)的基团,
其中式(X-1)至(X-9)中的虚线键指示与包含X1或X2的5元环连接的键;
R、R1在每次出现时相同或不同地表示H,D,F,Cl,Br,I,CHO,CN,N(Ar)2,C(=O)Ar,P(=O)(Ar)2,S(=O)Ar,S(=O)2Ar,NO2,Si(R3)3,B(OR3)2,OSO2R3,具有1至40个C原子的直链的烷基、烷氧基或硫代烷基基团或具有3至40个C原子的支链或环状的烷基、烷氧基或硫代烷基基团,所述烷基、烷氧基或硫代烷基基团中的每一个可以被一个或多个基团R3取代,其中在每种情况下一个或多个非相邻的CH2基团可以被R3C=CR3、C≡C、Si(R3)2、Ge(R3)2、Sn(R3)2、C=O、C=S、C=Se、P(=O)(R3)、SO、SO2、O、S或CONR3代替,并且其中一个或多个H原子可以被D、F、Cl、Br、I、CN或NO2代替,具有5至60个芳族环原子的芳族或杂芳族环系,在每种情况下所述芳族或杂芳族环系可以被一个或多个基团R3取代,或具有5至40个芳族环原子的芳氧基基团,所述芳氧基基团可以被一个或多个基团R3取代,其中两个基团R和/或两个基团R1可以形成单环或多环的脂族环系或芳族环系,所述脂族环系或芳族环系可以被一个或多个基团R3取代;
R2在每次出现时相同或不同地表示-C(=O)Ar1、-P(=O)(Ar1)2、-S(=O)Ar1、-S(=O)2Ar1、-SAr1、-B(Ar1)2或-P(Ar1)2;
R3在每次出现时相同或不同地表示H,D,F,Cl,Br,I,CHO,CN,N(Ar)2,C(=O)Ar,P(=O)(Ar)2,S(=O)Ar,S(=O)2Ar,NO2,Si(R4)3,B(OR4)2,OSO2R4,具有1至40个C原子的直链的烷基、烷氧基或硫代烷基基团或具有3至40个C原子的支链或环状的烷基、烷氧基或硫代烷基基团,所述烷基、烷氧基或硫代烷基基团中的每一个可以被一个或多个基团R4取代,其中在每种情况下一个或多个非相邻的CH2基团可以被R4C=CR4、C≡C、Si(R4)2、Ge(R4)2、Sn(R4)2、C=O、C=S、C=Se、P(=O)(R4)、SO、SO2、O、S或CONR4代替,并且其中一个或多个H原子可以被D、F、Cl、Br、I、CN或NO2代替,具有5至60个芳族环原子的芳族或杂芳族环系,在每种情况下所述芳族或杂芳族环系可以被一个或多个基团R4取代,或具有5至60个芳族环原子的芳氧基基团,所述芳氧基基团可以被一个或多个基团R4取代,其中两个基团R3可以形成单环或多环的脂族环系或芳族环系,所述脂族环系或芳族环系可以被一个或多个基团R4取代;
R4在每次出现时相同或不同地表示H,D,F,Cl,Br,I,CN,具有1至20个C原子的直链的烷基、烷氧基或硫代烷基基团或具有3至20个C原子的支链或环状的烷基、烷氧基或硫代烷基基团,其中在每种情况下一个或多个非相邻的CH2基团可以被SO、SO2、O、S代替,并且其中一个或多个H原子可以被D、F、Cl、Br或I代替,或具有5至24个C原子的芳族或杂芳族环系;
Ar、Ar1在每次出现时相同或不同地为具有5至60个芳族环原子的芳族或杂芳族环系,所述芳族或杂芳族环系在每种情况下还可以被一个或多个基团R4取代;
并且其中式(1)和(V-1)中包含基团W的两个6元环均带有至少一个取代基R2。
5.根据前述权利要求中的一项或多项所述的化合物,其特征在于R2选自-P(=O)(Ar1)2、-S(=O)Ar1和-S(=O)2Ar1。
6.根据前述权利要求中的一项或多项所述的化合物,其特征在于所述基团Ar1在每次出现时相同或不同地为选自苯、萘、蒽、联苯、三联苯、芴、呋喃、苯并呋喃、二苯并呋喃、噻吩、苯并噻吩、二苯并噻吩、咔唑、吲哚并咔唑、茚并咔唑或吡啶的芳族或杂芳族环系,所述基团中的每一个可以在任何自由位置处被一个或多个基团R4取代。
7.根据前述权利要求中的一项或多项所述的化合物,其特征在于所述基团Ar1在每次出现时相同或不同地为选自苯、萘、蒽、联苯、三联苯、芴的芳族或杂芳族环系,所述基团中的每一个可以在任何自由位置处被一个或多个基团R4取代。
8.根据前述权利要求中的一项或多项所述的化合物,其特征在于所述基团Ar1被至少一个氟原子或至少一个具有1至20个C原子的直链的氟代烷基基团或具有3至20个C原子的支链或环状的氟代烷基基团取代。
9.根据前述权利要求中的一项或多项所述的化合物,其特征在于X1和X2在每次出现时相同或不同地选自根据权利要求1中所定义的式(X-1)、(X-2)或(X-9)的基团。
10.根据权利要求9所述的化合物,其特征在于X1表示(X-1)并且X2表示(X-9),或特征在于X1表示(X-9)并且X2表示(X-1)。
11.根据权利要求9所述的化合物,其特征在于X1和X2均表示根据权利要求1中所定义的式(X-1)的基团。
12.一种制剂,所述制剂包含至少一种根据权利要求1至11中的一项或多项所述的化合物和至少一种溶剂。
13.一种包含至少一种根据权利要求1至11中的一项或多项所述的化合物的电子器件,所述电子器件选自有机电致发光器件、有机集成电路、有机场效应晶体管、有机薄膜晶体管、有机发光晶体管、有机太阳能电池、染料敏化的有机太阳能电池、有机光学检测器、有机光感受器、有机场猝熄器件、发光电化学电池、有机激光二极管以及有机等离子体激元发光器件。
14.根据权利要求13所述的电子器件,所述电子器件为有机电致发光器件,其特征在于根据权利要求1至11中的一项或多项所述的化合物用作空穴注入层中的空穴注入材料或用作空穴注入或空穴传输性层中的p型掺杂剂。
15.根据权利要求14所述的电子器件,其特征在于所述有机电致发光器件包含阴极、阳极、布置在所述阳极与所述阴极之间的至少一个发光层、布置在所述阳极与所述至少一个发光层之间的至少一个空穴传输层和布置在所述阳极与所述至少一个空穴传输层之间的至少一个空穴注入层,其特征在于所述至少一个空穴注入层包含对应于根据权利要求1至11中的一项或多项所述的化合物的电子受体材料。
16.根据权利要求14所述的电子器件,其特征在于所述有机电致发光器件包含阴极、阳极、布置在所述阳极与所述阴极之间的至少一个发光层、布置在所述阳极与所述至少一个发光层之间的至少一个空穴传输层和布置在所述阳极与所述至少一个空穴传输层之间的至少一个空穴注入层,其特征在于所述至少一个空穴注入层或所述至少一个空穴传输层包含对应于根据权利要求1至11中的一项或多项所述的化合物的p型掺杂剂。
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US20210020843A1 (en) | 2021-01-21 |
TW201945514A (zh) | 2019-12-01 |
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