CN111718333A - 1,3-二氮杂芴化合物和电子器件 - Google Patents
1,3-二氮杂芴化合物和电子器件 Download PDFInfo
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- CN111718333A CN111718333A CN202010641980.9A CN202010641980A CN111718333A CN 111718333 A CN111718333 A CN 111718333A CN 202010641980 A CN202010641980 A CN 202010641980A CN 111718333 A CN111718333 A CN 111718333A
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- diazafluorene
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- KPXWJZVFWZHULA-UHFFFAOYSA-N 9h-indeno[2,1-d]pyrimidine Chemical class N1=CN=C2CC3=CC=CC=C3C2=C1 KPXWJZVFWZHULA-UHFFFAOYSA-N 0.000 title abstract description 12
- -1 1, 3-diazafluorene compound Chemical class 0.000 claims abstract description 186
- 239000000463 material Substances 0.000 claims abstract description 49
- 230000000903 blocking effect Effects 0.000 claims abstract description 26
- 238000002347 injection Methods 0.000 claims abstract description 26
- 239000007924 injection Substances 0.000 claims abstract description 26
- 230000005525 hole transport Effects 0.000 claims abstract description 16
- 230000005669 field effect Effects 0.000 claims abstract description 7
- 239000010410 layer Substances 0.000 claims description 142
- 125000004432 carbon atom Chemical group C* 0.000 claims description 95
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 33
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 239000012044 organic layer Substances 0.000 claims description 20
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 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 9
- 235000010290 biphenyl Nutrition 0.000 claims description 9
- 239000004305 biphenyl Substances 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000004431 deuterium atom Chemical group 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 229910052805 deuterium Inorganic materials 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 125000004306 triazinyl group Chemical group 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000006267 biphenyl group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 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 claims 1
- DERKMBVPWKXOHM-UHFFFAOYSA-N 12h-[1]benzofuro[3,2-a]carbazole Chemical compound O1C2=CC=CC=C2C2=C1C=CC1=C2NC2=CC=CC=C12 DERKMBVPWKXOHM-UHFFFAOYSA-N 0.000 claims 1
- GLYYLMBVQZMMMS-UHFFFAOYSA-N 12h-[1]benzothiolo[3,2-a]carbazole Chemical compound S1C2=CC=CC=C2C2=C1C=CC1=C2NC2=CC=CC=C12 GLYYLMBVQZMMMS-UHFFFAOYSA-N 0.000 claims 1
- BAWARCCDOBENCG-UHFFFAOYSA-N 19-azaheptacyclo[15.11.0.02,14.03,11.05,10.018,26.020,25]octacosa-1(28),2,4,6,8,10,12,14,16,18,20,22,24,26-tetradecaene Chemical compound C1=CC=CC=2N=C3C=4C(=CC=C3C1=2)C=1C(C=CC2=C3C=CC=CC3=CC=12)=CC=4 BAWARCCDOBENCG-UHFFFAOYSA-N 0.000 claims 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims 1
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 claims 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
- 125000005580 triphenylene group Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 6
- 239000000470 constituent Substances 0.000 abstract description 3
- 238000011161 development Methods 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- 239000010408 film Substances 0.000 description 38
- 238000000034 method Methods 0.000 description 31
- 125000001424 substituent group Chemical group 0.000 description 29
- 150000001875 compounds Chemical class 0.000 description 27
- 230000015572 biosynthetic process Effects 0.000 description 20
- 239000000543 intermediate Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 238000002156 mixing Methods 0.000 description 14
- 239000000758 substrate Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 238000007740 vapor deposition Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- 239000010409 thin film Substances 0.000 description 7
- OMBVEVHRIQULKW-DNQXCXABSA-M (3r,5r)-7-[3-(4-fluorophenyl)-8-oxo-7-phenyl-1-propan-2-yl-5,6-dihydro-4h-pyrrolo[2,3-c]azepin-2-yl]-3,5-dihydroxyheptanoate Chemical compound O=C1C=2N(C(C)C)C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C=3C=CC(F)=CC=3)C=2CCCN1C1=CC=CC=C1 OMBVEVHRIQULKW-DNQXCXABSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 229940126540 compound 41 Drugs 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- UMJJFEIKYGFCAT-UHFFFAOYSA-N indan-2-one Chemical compound C1=CC=C2CC(=O)CC2=C1 UMJJFEIKYGFCAT-UHFFFAOYSA-N 0.000 description 5
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 5
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000002356 single layer Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000007772 electrode material Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000001041 indolyl group Chemical group 0.000 description 4
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 4
- 125000005493 quinolyl group Chemical group 0.000 description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 4
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical class C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 4
- STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 3
- JAUCIDPGGHZXRP-UHFFFAOYSA-N 4-phenyl-n-(4-phenylphenyl)aniline Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1NC(C=C1)=CC=C1C1=CC=CC=C1 JAUCIDPGGHZXRP-UHFFFAOYSA-N 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 150000001454 anthracenes Chemical class 0.000 description 3
- 125000005874 benzothiadiazolyl group Chemical group 0.000 description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 229940125878 compound 36 Drugs 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 125000005956 isoquinolyl group Chemical group 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 3
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 3
- 125000003226 pyrazolyl group Chemical group 0.000 description 3
- 125000001725 pyrenyl group Chemical group 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 125000000168 pyrrolyl group Chemical group 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 125000001544 thienyl group Chemical group 0.000 description 3
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical group C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 2
- 238000001194 electroluminescence spectrum Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 2
- 238000002189 fluorescence spectrum Methods 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 2
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 2
- 229910017053 inorganic salt Inorganic materials 0.000 description 2
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 2
- 125000005990 isobenzothienyl group Chemical group 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000000842 isoxazolyl group Chemical group 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 2
- ZTLUNQYQSIQSFK-UHFFFAOYSA-N n-[4-(4-aminophenyl)phenyl]naphthalen-1-amine Chemical compound C1=CC(N)=CC=C1C(C=C1)=CC=C1NC1=CC=CC2=CC=CC=C12 ZTLUNQYQSIQSFK-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 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 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 150000007978 oxazole derivatives Chemical class 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 2
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 2
- 125000005561 phenanthryl group Chemical group 0.000 description 2
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 150000003220 pyrenes Chemical class 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- 150000004322 quinolinols Chemical class 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 2
- 125000003831 tetrazolyl group Chemical group 0.000 description 2
- 125000005259 triarylamine group Chemical group 0.000 description 2
- 150000003918 triazines Chemical class 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
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- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical class [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
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- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
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- 125000005063 tetradecenyl group Chemical group C(=CCCCCCCCCCCCC)* 0.000 description 1
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- 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 1
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- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
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- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明涉及1,3‑二氮杂芴化合物和电子器件。本发明的1,3‑二氮杂芴化合物通过引入1,3‑二氮杂芴刚性结构,其的成膜性和热稳定性优异,可用于制备有机电致发光器件、有机场效应晶体管和有机太阳能电池。另外,本发明的1,3‑二氮杂芴化合物可以作为空穴注入层、空穴传输层、发光层、电子阻挡层、空穴阻挡层或电子传输层的构成材料,能够降低驱动电压,提高效率、亮度和寿命等。此外,本发明的1,3‑二氮杂芴化合物的制备方法简单,原料易得,能够满足工业化的发展需求。
Description
技术领域
本发明属于有机光电材料技术领域,涉及1,3-二氮杂芴化合物和包含该1,3-二氮杂芴化合物的电子器件。更具体地,本发明涉及适用于电子器件,特别是有机电致发光器件、有机场效应晶体管和有机太阳能电池的1,3-二氮杂芴化合物以及使用了该1,3-二氮杂芴化合物的电子器件。
背景技术
有机电致发光器件具有自主发光、低电压驱动、全固化、宽视角、组成和工艺简单等一系列的优点,与液晶显示器相比,有机电致发光器件不需要背光源。因此,有机电致发光器件具有广泛的应用前景。
有机电致发光器件一般包括阳极、金属阴极和它们之间夹着的有机层。有机层主要包括空穴注入层、空穴传输层、电子阻挡层、发光层、空穴阻挡层、电子传输层、电子注入层。另外,发光层大多采用主客体结构。即,将发光材料以一定浓度掺杂在主体材料中,以避免浓度淬灭和三线态-三线态湮灭,提高发光效率。因此,一般要求主体材料具有较高的三线态能级,并且同时具有较高的稳定性。
目前,有机电致发光材料的研究已经在学术界和工业界广泛开展,大量性能优良的有机电致发光材料陆续被开发出来。总体来看,未来有机电致发光器件的方向是发展高效率、长寿命、低成本的白光器件和全彩色显示器件,但该技术的产业化进程仍面临许多关键问题。因此,设计与寻找一种稳定高效的化合物,作为有机电致发光器件新型材料以克服其在实际应用过程中出现的不足,是有机电致发光器件材料研究工作中的重点与今后的研发趋势。
发明内容
发明要解决的问题
本发明的目的在于,提供一种1,3-二氮杂芴化合物。本发明的1,3-二氮杂芴化合物热稳定性高、传输性能好、制备方法简单,并且由该1,3-二氮杂芴化合物制成的有机发光器件,表现出发光效率高、寿命长、驱动电压低的优点,是性能优良的有机电致发光材料。
本发明的另一个目的是提供一种使用该1,3-二氮杂芴化合物的电子器件,该电子器件具有高效率、高耐久性和长寿命的优点。
用于解决问题的方案
1,3-二氮杂芴化合物具有特殊的联苯结构,具有较高热稳定性、化学稳定性和载流子传输性,更重要的是1,3-二氮杂芴化合物中的两个sp2杂化氮原子具有明显的吸电子特性,搭配不同的给体和受体单元可以实现合适的单线态、三线态以及分子轨道能级。因此将其引入到具有电致发光特性的分子中,有利于提高器件的稳定性和发光效率,降低器件驱动电压。
即,本发明的方案如前述的技术方案所示。
发明的效果
本发明的1,3-二氮杂芴化合物通过引入1,3-二氮杂芴刚性结构,具有良好的成膜性和热稳定性,可用于制备有机电致发光器件、有机场效应晶体管和有机太阳能电池等电子器件,尤其是作为有机电致发光器件中的空穴注入层、空穴传输层、发光层、电子阻挡层、空穴阻挡层或电子传输层的构成材料,能够表现出发光效率高、寿命长且驱动电压低的优点,显著优于现有有机电致发光器件。
另外,本发明的1,3-二氮杂芴化合物的制备方法简单,原料易得,能够满足工业化的发展需求。
本发明的1,3-二氮杂芴化合物在有机电致发光器件、有机场效应晶体管和有机太阳能电池等电子器件中具有良好的应用效果,具有广泛的产业化前景。
本发明的1,3-二氮杂芴化合物具有高的电子注入和移动速率。因此,利用具有使用本发明的1,3-二氮杂芴化合物制备的电子注入层和/或电子传输层的有机电致发光器件,提高了从电子传输层到发光层的电子传输效率,从而提高发光效率。并且,降低了驱动电压,从而增强所得的有机电致发光器件的耐久性。
本发明的1,3-二氮杂芴化合物具有优异的阻断空穴的能力,电子传输性能优异,并且在薄膜状态下是稳定的。因此,具有使用本发明的1,3-二氮杂芴化合物制备的空穴阻挡层的有机电致发光器件具有高的发光效率,驱动电压降低,并且电流耐性改善,使得有机电致发光器件的最大发光亮度增加。
本发明的1,3-二氮杂芴化合物可用作有机电致发光器件的空穴注入层、空穴传输层、发光层、电子阻挡层、空穴阻挡层或电子传输层的构成材料。使用本发明的有机电致发光器件,可以限制在发光层内产生的激子,并且可以进一步增加空穴和电子的重新结合的可能性,以获得高发光效率。此外,驱动电压如此之低,因而可以实现高耐久性。
附图说明
图1为本发明实施例3(化合物41)在二氯甲烷溶液中的荧光光谱(PL)。
图2为本发明实施例6(有机电致发光器件3)的电致发光光谱。
图3是显示实施例4~6的有机电致发光器件以及比较例1和2的有机电致发光器件的构造的图。
附图标记说明
1 基板
2 阳极
3 空穴注入层
4 空穴传输层
5 电子阻挡层
6 发光层
7 空穴阻挡层
8 电子传输层
9 电子注入层
10 阴极
具体实施方式
以下,对本发明的实施方式进行详细说明。但是,本发明不受以下实施方式的限定。
本发明的1,3-二氮杂芴化合物是具有芴环结构的新型化合物,并且由下述通式(1)表示。
具体地,本发明的1,3-二氮杂芴化合物具有下列通式(I)或(II)的结构:
在上述通式(1)、(I)以及(II)中,
L1和L2各自独立地表示单键、羰基、具有6至18个碳原子的芳香族烃基或具有5至18个碳原子的芳香族杂环基中的一个或多个;
Ar1~Ar4各自独立地表示任选被一个或多个R1取代的、具有6至30个碳原子的芳香族烃基或任选被一个或多个R1取代的、具有5至30个碳原子的芳香族杂环基中的一个或多个;
X和Y各自独立地表示取代或未取代的具有1至8个碳原子的烷基、取代或未取代的具有6至24个碳原子的芳香族烃基或取代或未取代的具有5至23个碳原子的芳香族杂环基中的一个或多个,或者它们可以连接成环;
m和n各自独立地为0~4的整数,并且m和n不同时为0;
R1表示氢原子、氘原子、氟原子、氯原子、溴原子、碘原子、氰基、NO2、N(R2)2、OR2、SR2、C(=O)R2、P(=O)R2、Si(R2)3、取代或未取代的具有1至20个碳原子的烷基、取代或未取代的具有2至20个碳原子的烯基、取代或未取代的具有2至20个碳原子的炔基、取代或未取代的具有6至40个碳原子的芳香族烃基、或取代或未取代的具有5至40个碳原子的芳香族杂环基中的一个或多个;
R2表示氢原子、氘原子、氟原子、氰基、取代或未取代的具有1至20个碳原子的烷基、取代或未取代的具有6至30个碳原子的芳香族烃基或取代或未取代的具有5至30个碳原子的芳香族杂环基中的一个或多个。
<L1和L2>
L1和L2各自独立地表示单键、羰基、具有6至18个碳原子的芳香族烃基或具有5至18个碳原子的芳香族杂环基中的一个或多个。
在本发明中,具有5至18个碳原子的芳香族杂环基中的杂原子优选自N、O和/或S。在本发明中,杂原子的数目可以是1~5个。本发明意义上的芳香族烃基或芳香族杂环基是指如下的体系,该体系并不必须仅含有芳基或杂芳基基团,而是其中多个芳基或杂芳基基团还可以被非芳香族单元(优选小于非氢原子的10%)间断,该非芳香族单元例如可以是碳原子、氮原子、氧原子或者羰基基团。例如,和两个或多个芳基基团例如被直链或环状的烷基基团或者被甲硅烷基基团间断的体系一样,9,9’-螺二芴、9,9-二芳基芴、三芳基胺、二芳基醚等的体系也旨在被认为是本发明意义上的芳香族烃基。此外,其中两个或多个芳基或杂芳基基团相互直接键合的体系,例如联苯、三联苯或四联苯,同样也旨在被认为是芳香族烃基或芳香族杂环基。
由L1和L2表示的具有6至18个碳原子的芳香族烃基或具有5至18个碳原子的芳香族杂环基可以例示出:苯基、萘基、蒽基、苯并蒽基、菲基、苯并菲基、芘基、苝基、荧蒽基、苯并荧蒽基、并四苯基、并五苯基、苯并芘基、联苯基、偶苯基、三联苯基、四联苯基、五联苯基、三聚苯基、芴基、螺双芴基、二氢菲基、二氢芘基、四氢芘基、顺式或反式茚并芴基、顺式或反式单苯并茚并芴基、顺式或反式二苯并茚并芴基、三聚茚基、异三聚茚基、螺三聚茚基、螺异三聚茚基、呋喃基、苯并呋喃基、异苯并呋喃基、二苯并呋喃基、噻吩基、苯并噻吩基、异苯并噻吩基、二苯并噻吩基、吡咯基、吲哚基、异吲哚基、咔唑基、吲哚并咔唑基、茚并咔唑基、吡啶基、喹啉基、异喹啉基、吖啶基、菲啶基、苯并-5,6-喹啉基、苯并-6,7-喹啉基、苯并-7,8-喹啉基、吩噻嗪基、吩噁嗪基、吡唑基、吲唑基、咪唑基、苯并咪唑基、萘并咪唑基、菲并咪唑基、吡啶并咪唑基、吡嗪并咪唑基、喹喔啉并咪唑基、噁唑基、苯并噁唑基、萘并噁唑基、蒽并噁唑基、菲并噁唑基、异噁唑基、1,2-噻唑基、1,3-噻唑基、苯并噻唑基、哒嗪基、苯并哒嗪基、嘧啶基、苯并嘧啶基、喹喔啉基、1,5-二氮杂蒽基、2,7-二氮杂芘基、2,3-二氮杂芘基、1,6-二氮杂芘基、1,8-二氮杂芘基、4,5-二氮杂芘基、4,5,9,10-四氮杂苝基、吡嗪基、吩嗪基、吩噁嗪基、吩噻嗪基、荧红环基、萘啶基、氮杂咔唑基、苯并咔啉基、菲咯啉基、1,2,3-***基、1,2,4-***基、苯并***基、1,2,3-噁二唑基、1,2,4-噁二唑基、1,2,5-噁二唑基、1,3,4-噁二唑基、1,2,3-噻二唑基、1,2,4-噻二唑基、1,2,5-噻二唑基、1,3,4-噻二唑基、1,3,5-三嗪基、1,2,4-三嗪基、1,2,3-三嗪基、四唑基、1,2,4,5-四嗪基、1,2,3,4-四嗪基、1,2,3,5-四嗪基、嘌呤基、蝶啶基、吲嗪基、苯并噻二唑基等。
在本发明中,优选地,L1和L2各自独立地表示单键、羰基、具有6至12个碳原子的芳香族烃基或具有5至12个碳原子的芳香族杂环基中的一个或多个。更优选地,L1和L2各自独立地表示单键、羰基、苯基、三嗪基或联苯基中的一个或多个。
由L1和L2表示的具有6至18个碳原子的芳香族烃基或具有5至18个碳原子的芳香族杂环基可以是未取代的,但也可以具有取代基。取代基可以例示如下:氘原子;氰基;硝基;卤素原子,例如氟原子、氯原子、溴原子或碘原子;具有1至6个碳原子的烷基,例如,甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、异戊基、新戊基或正己基;具有1至6个碳原子的烷氧基,例如甲氧基、乙氧基或丙氧基;烯基,例如乙烯基或烯丙基;芳氧基,例如苯氧基或甲苯氧基;芳基烷氧基,例如苄氧基或苯乙氧基;芳族烃基或稠合多环芳族基,例如苯基、联苯基、三联苯基、萘基、蒽基、菲基、芴基、茚基、芘基、苝基、荧蒽基、苯并[9,10]菲基或螺二芴基;芳族杂环基,例如吡啶基、噻吩基、呋喃基、吡咯基、喹啉基、异喹啉基、苯并呋喃基、苯并噻吩基、吲哚基、咔唑基、苯并噁唑基、苯并噻唑基、喹喔啉基、苯并咪唑基、吡唑基、二苯并呋喃基、二苯并噻吩基、氮杂芴基、二氮杂芴基、咔啉基、氮杂螺二芴基或二氮杂螺二芴基;芳基乙烯基,例如苯乙烯基或萘乙烯基;和酰基,例如乙酰基或苯甲酰基等。
具有1至6个碳原子的烷基和具有1至6个碳原子的烷氧基可以是直链或者支链的。任何上述取代基可以进一步被上述示例性取代基取代。上述取代基可以彼此独立地存在,但也可以经由单键、取代或未取代的亚甲基、氧原子或硫原子彼此键合形成环。
<A1和A2>
(Ar1至Ar4)
Ar1~Ar4各自独立地表示任选被一个或多个R1取代的、具有6至30个碳原子的芳香族烃基或任选被一个或多个R1取代的、具有5至30个碳原子的芳香族杂环基中的一个或多个。
由Ar1~Ar4表示的具有6至30个碳原子的芳香族烃基或具有5至30个碳原子的芳香族杂环基可以例示出:苯基、萘基、蒽基、苯并蒽基、菲基、苯并菲基、芘基、苝基、荧蒽基、苯并荧蒽基、并四苯基、并五苯基、苯并芘基、联苯基、偶苯基、三联苯基、四联苯基、五联苯基、三聚苯基、芴基、螺双芴基、二氢菲基、二氢芘基、四氢芘基、顺式或反式茚并芴基、顺式或反式单苯并茚并芴基、顺式或反式二苯并茚并芴基、三聚茚基、异三聚茚基、螺三聚茚基、螺异三聚茚基、呋喃基、苯并呋喃基、异苯并呋喃基、二苯并呋喃基、噻吩基、苯并噻吩基、异苯并噻吩基、二苯并噻吩基、苯并噻吩并咔唑基、吡咯基、吲哚基、异吲哚基、咔唑基、吲哚并咔唑基、茚并咔唑基、吡啶基、联吡啶基、三联吡啶基、喹啉基、异喹啉基、吖啶基、菲啶基、苯并-5,6-喹啉基、苯并-6,7-喹啉基、苯并-7,8-喹啉基、吩噻嗪基、吩噁嗪基、吡唑基、吲唑基、咪唑基、苯并咪唑基、萘并咪唑基、菲并咪唑基、吡啶并咪唑基、吡嗪并咪唑基、喹喔啉并咪唑基、噁唑基、苯并噁唑基、苯并噁二唑基、萘并噁唑基、蒽并噁唑基、菲并噁唑基、异噁唑基、噻唑基、异噻唑基、苯并噻唑基、苯并噻二唑基、哒嗪基、苯并哒嗪基、嘧啶基、苯并嘧啶基、喹喔啉基、喹唑啉基、氮杂芴基、二氮杂蒽基、二氮杂芘基、四氮杂苝基、二氮杂萘基、吡嗪基、吩嗪基、吩噁嗪基、吩噻嗪基、荧红环基、萘啶基、氮杂咔唑基、苯并咔啉基、菲咯啉基、***基、苯并***基、噁二唑基、噻二唑基、三嗪基、四唑基、四嗪基、嘌呤基、蝶啶基、吲嗪基、苯并噻二唑基、吡啶并吡咯基、吡啶并***基、呫吨基、苯并呋喃并咔唑基、苯并芴并咔唑基、N-苯基咔唑基、二苯基-苯并咪唑基、二苯基-噁二唑基、二苯基硼基、三苯基磷氧基、二苯基磷氧基、三苯基硅基、四苯基硅基等。
在本发明中,优选地,Ar1~Ar4各自独立地选自下述基团:
其中,虚线表示与L1、L2或N键合的键;
R1具有上述所定义的含义。
由Ar1~Ar4表示的具有6至30个碳原子的芳香族烃基或具有5至30个碳原子的芳香族杂环基可以是未取代的,但也可以具有取代基。优选地,由Ar1~Ar4表示的具有6至30个碳原子的芳香族烃基或具有5至30个碳原子的芳香族杂环基是被一个或多个R1取代的、具有5至30个碳原子的芳香族烃基或被一个或多个R1取代的、具有5至30个碳原子的芳香族杂环基。
(R1)
R1表示氢原子、氘原子、氟原子、氯原子、溴原子、碘原子、氰基、NO2、N(R2)、OR2、SR2、C(=O)R2、P(=O)R2、Si(R2)3、取代或未取代的具有1至20个碳原子的烷基、取代或未取代的具有2至20个碳原子的烯基、取代或未取代的具有2至20个碳原子的炔基、取代或未取代的具有6至40个碳原子的芳香族烃基、或取代或未取代的具有5至40个碳原子的芳香族杂环基中的一个或多个。
由R1表示的具有1至20个碳原子的烷基可以例示出:甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、异戊基、新戊基、正己基、正庚基、2-甲基己基、正辛基、异辛基、叔辛基、2-乙基己基、3-甲基庚基、正壬基、正癸基、十六烷基、十八烷基、二十烷基、环丙基、环丁基、环戊基、3-甲基环戊基、2,3-二甲基环戊基、环己基、3-甲基环己基、4-甲基环己基、2,3-二甲基环己基、3,4,5-三甲基环己基、4-叔丁基环己基、环庚基、环辛基等。具有1至20个碳原子的烷基可以是直链、支链或环状的。
由R1表示的具有1至20个碳原子的烷基可以是未取代的,但也可具有取代基。优选地,由R1表示的具有1至20个碳原子的烷基被一个或多个下述R2取代。另外,所述烷基中的一个或多个非相邻的CH2基团可以被R2C=CR2、C≡C、Si(R2)3、C=O、C=NR2、P(=O)R2、SO、SO2、NR2、O、S或CONR2代替,并且其中一个或者多个氢原子可以被氘原子、氟原子、氯原子、溴原子、碘原子、氰基、硝基代替。
由R1表示的具有2至20个碳原子的烯基可以例示出:乙烯基、丙烯基、丁烯基、戊烯基、己烯基、庚烯基、辛烯基、壬烯基、癸烯基、十一烯基、十二烯基、十三烯基、十四烯基、十五烯基、十六烯基、十七烯基、十八烯基、十九烯基、二十烯基、2-乙基己烯基、烯丙基或环己烯基等。具有2至20个碳原子的烯基可以是直链、支链或环状的。
由R1表示的具有2至20个碳原子的烯基可以是未取代的,或可以具有取代基。取代基可以例示为与由R1表示的具有1至20个碳原子的烷基任选地具有的取代基所示的相同的取代基。取代基可以采用的模式与示例性取代基的模式相同。
由R1表示的具有2至20个碳原子的炔基可以例示出:乙炔基、异丙炔基、丁炔基、戊炔基、己炔基、庚炔基、辛炔基、壬炔基、癸炔基等。
由R1表示的具有2至20个碳原子的炔基可以是未取代的,或可以具有取代基。取代基可以例示为与由R1表示的具有1至20个碳原子的烷基任选地具有的取代基所示的相同的取代基。取代基可以采用的模式与示例性取代基的模式相同。
由R1表示的具有6至40个碳原子的芳香族烃基或具有5至40个碳原子的芳香族杂环基可以列举出于前述由Ar1~Ar4表示的具有6至30个碳原子的芳香族烃基或具有5至30个碳原子的芳香族杂环基示出的基团相同的基团。
由R1表示的具有6至40个碳原子的芳香族烃基或具有5至40个碳原子的芳香族杂环基可以是未取代的,或可以具有取代基。取代基可以例示为与由R1表示的具有1至20个碳原子的烷基任选地具有的取代基所示的相同的取代基。取代基可以采用的模式与示例性取代基的模式相同。此外,两个相邻的R1取代基或两个相邻的R2取代基任选可形成单环或多环的脂肪族、芳香族或者杂芳香族的环系,所述环系可以被一个或多个R2取代;在此处两个或多个取代基R1可以彼此连接并可以形成环。
作为优选的由R1表示的具有6至40个碳原子的芳香族烃基或具有5至40个碳原子的芳香族杂环基,可以列举:苯基、联苯基、三联苯基、四联苯基、五联苯基、苯并噻吩并咔唑基、苯并呋喃并咔唑基、苯并芴并咔唑基、苯并蒽基、苯并菲基、芴基、螺双芴基、三嗪基、二苯并呋喃基、二苯并噻吩基、咔唑基、N-苯基咔唑基、茚并咔唑基、苯并咪唑基、二苯基-苯并咪唑基、二苯基-噁二唑基、二苯基硼基、三苯基磷氧基、二苯基磷氧基、三苯基硅基、四苯基硅基等。所述具有6至40个碳原子的芳香族烃基或具有5至40个碳原子的芳香族杂环基可以被一个或多个R2取代。
(R2)
R2表示氢原子、氘原子、氟原子、氰基、取代或未取代的具有1至20个碳原子的烷基、取代或未取代的具有6至30个碳原子的芳香族烃基或取代或未取代的具有5至30个碳原子的芳香族杂环基中的一个或多个。
由R2表示的具有1至20个碳原子的烷基可以列举出于前述由R1表示的具有1至20个碳原子的烷基示出的基团相同的基团。
由R2表示的具有6至30个碳原子的芳香族烃基或取代或未取代的具有5至30个碳原子的芳香族杂环基可以列举出与前述由R1表示的具有6至30个碳原子的芳香族烃基或取代或未取代的具有5至30个碳原子的芳香族杂环基示出的基团相同的基团。
由R2表示的具有1至20个碳原子的烷基、具有6至30个碳原子的芳香族烃基或取代或未取代的具有5至30个碳原子的芳香族杂环基可以是未取代的,或也可以具有取代基。取代基可以例示出:氘原子;卤素原子,例如氟原子、氯原子、溴原子或碘原子;氰基等。
(X和Y)
X和Y各自独立地表示取代或未取代的具有1至8个碳原子的烷基、取代或未取代的具有6至24个碳原子的芳香族烃基或取代或未取代的具有5至23个碳原子的芳香族杂环基,或者它们可以连接成环。
具体地,X和Y各自独立地表示甲基、乙基、苯基中的一个或多个;或者X和Y可以连接形成螺芴基、螺环三苯胺基、螺环苯基咔唑基或环戊烷基。
(m和n)
m和n分别表示与1,3-二氮杂芴环骨架结构相连的-L1-A1结构单元和-L2-A2结构单元的数目,在本发明中,m和n各自独立地为0~4的整数,并且m和n不同时为0。优选地,m和n各自独立地为0~2的整数,更优选为0、1或2,但不同时为0。
<制造方法>
本发明的1,3-二氮杂芴化合物例如可以通过以下方法制造:
所得化合物的纯化可以例如通过使用柱色谱法的纯化,使用硅胶、活性炭、活性粘土等的吸附纯化,使用溶剂的重结晶或结晶,升华纯化等来进行。化合物的鉴定可以通过质谱、元素分析进行。
在本发明的1,3-二氮杂芴化合物中,优选的化合物的具体实例如下所示,但本发明绝不限于这些化合物。
<电子器件>
多种含有本发明的1,3-二氮杂芴化合物的电子器件可以将根据本发明的1,3-二氮杂芴化合物用于生产可以特别地以层的形式配置的有机材料来生产。特别地,本发明的1,3-二氮杂芴化合物可以用于有机电致发光器件、有机太阳能电池、有机二极管特别是有机场效应晶体管。特别是在有机电致发光器件或太阳能电池的情况下,组件可以具有插销结构(器件具有一个或多个p-掺杂的空穴传输层和/或一个或多个n-掺杂的电子传输层)或倒置结构(从发光层看,上电极和空穴传输层位于相同侧同时基板在相对侧),没有限定为这些结构。注入层、传输层、发光层、阻挡层等例如可以通过在电极之间形成包含根据本发明的1,3-二氮杂芴化合物或由根据本发明的1,3-二氮杂芴化合物组成的层来制作。然而,根据本发明的1,3-二氮杂芴化合物的使用不限于上述示例性实施方案。
<有机电致发光器件>
本发明的有机电致发光器件包括:第一电极、与第一电极对置而具备的第二电极、以及夹在第一电极与第二电极之间的至少一个有机层,其中所述至少一个有机层包含本发明的1,3-二氮杂芴化合物。
图3是显示本发明的有机电致发光器件的构造的图。如图3所示,在本发明的有机电致发光器件中,例如,阳极2、空穴注入层3、空穴传输层4、电子阻挡层5、发光层6、空穴阻挡层7、电子传输层8、电子注入层9和阴极10依次设置在基板1上。
本发明的有机电致发光器件不限于这样的结构,例如在该多层结构中,可以省略一些有机层。例如,可以是阳极2与空穴传输层4之间的空穴注入层3、发光层6与电子传输层8之间的空穴阻挡层7、以及电子传输层8与阴极10之间的电子注入层9被省略,并且在基板1上依次设置阳极2、空穴传输层4、发光层6、电子传输层8和阴极10的构型。
根据本发明的有机电致发光器件除了上述有机层包含由上述通式(1)表示的化合物以外,可以通过本领域技术领域公知的材料和方法进行制造。另外,在上述有机电致发光器件包含多个有机层的情况下,上述有机层可以由相同的物质或不同的物质形成。
例如,根据本发明的有机电致发光器件可以通过在基板上依次层叠第一电极、有机层和第二电极而制造。此时,可以如下制造:利用溅射法或电子束蒸发法之类的PVD(物理蒸镀法)方法,在基板上蒸镀金属或具有导电性的金属氧化物或它们的合金而形成阳极,然后在该阳极上形成包含空穴注入层、空穴传输层、发光层和电子传输层的有机层,之后在该有机物层上蒸镀可用作阴极的物质。但是,制造方法并不限定于此。
作为一个例子,上述第一电极为阳极,上述第二电极为阴极,或者上述第一电极为阴极,上述第二电极为阳极。
作为本发明的有机电致发光器件的阳极,可以由公知的电极材料构成。例如使用具有大的功函数的电极材料,如钒、铬、铜、锌、金等金属或它们的合金;如氧化锌、氧化铟、氧化铟锡(ITO)、氧化铟锌(IZO)等金属氧化物;如ZnO:Al或SNO2:Sb等金属与氧化物的组合;聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧)噻吩](PEDOT)、聚吡咯和聚苯胺等导电性高分子等。这些之中,优选ITO。
作为本发明的有机电致发光器件的空穴注入层,可以使用公知的具有空穴注入性质的材料。例如可列举:以铜酞菁为代表的卟啉化合物、萘二胺化合物、星型的三苯胺化合物、分子中具有3个以上三苯胺结构通过单键或不含杂原子的二价基团连接的结构的芳胺化合物等三苯胺三聚体及四聚体、六氰基氮杂苯并菲等受体型杂环化合物、涂布型高分子材料。这些材料可以通过蒸镀法、以及旋涂法、喷墨法等公知方法来形成薄膜。
作为本发明的有机电致发光器件的空穴传输层,优选使用包含本发明的1,3-二氮杂芴化合物。除此之外,还可以使用公知的其他具有空穴传输性的材料。例如可列举:含有间咔唑基苯基的化合物;如N,N′-二苯基-N,N′-二(间甲苯基)联苯胺(TPD)、N,N′-二苯基-N,N′-(1-萘基)-1,1'-联苯-4,4'-二胺(NPB)、N,N,N′,N′-四联苯基联苯胺等联苯胺衍生物;1,1-双[(二-4-甲苯基氨基)苯基]环己烷(TAPC);各种三苯胺三聚体及四聚体;9,9′,9″-三苯基-9H,9′H,9″H-3,3′:6′,3″-三咔唑(Tris-PCz)等。它们可以单独地成膜,也可以以与其它材料一起混合成膜而成的单层的形式来使用,还可以制成单独成膜而成的层彼此的层叠结构、混合成膜而成的层彼此的层叠结构、或者单独成膜而成的层与混合成膜而成的层的层叠结构。这些材料可以通过蒸镀法、以及旋涂法、喷墨法等公知方法来形成薄膜。
此外,空穴注入层或空穴传输层中,也可以使用对于该层中通常使用的材料进一步P掺杂三溴苯胺六氯化锑、轴烯衍生物等而成的物质、其部分结构中具有TPD等联苯胺衍生物的结构的高分子化合物等。
作为本发明的有机电致发光器件的电子阻挡层,优选使用本发明的1,3-二氮杂芴化合物。除此之外,还可以使用其他具有电子阻挡作用的公知化合物形成。例如,可列举出:4,4′,4″-三(N-咔唑基)三苯胺(TCTA)、9,9-双[4-(咔唑-9-基)苯基]芴、1,3-双(咔唑-9-基)苯(mCP)、2,2-双(4-咔唑-9-基苯基)金刚烷(Ad-Cz)等咔唑衍生物;9-[4-(咔唑-9-基)苯基]-9-[4-(三苯基甲硅烷基)苯基]-9H-芴所代表的具有三苯基甲硅烷基和三芳胺结构的化合物;电子阻挡性高的单胺化合物、各种三苯胺二聚体等具备电子阻挡作用的化合物。它们可以单独地成膜,也可以与其它材料一起混合成膜而成的单层的形式来使用,还可以制成单独成膜而成的层彼此的层叠结构、混合成膜而成的层彼此的层叠结构、或者单独成膜而成的层与混合成膜而成的层的层叠结构。这些材料可以通过蒸镀法、以及旋涂法、喷墨法等公知方法来形成薄膜。
作为本发明的有机电致发光器件的发光层,优选使用本发明的1,3-二氮杂芴化合物。除此之外,还可以使用以Alq3为首的羟基喹啉衍生物的金属络合物等各种金属络合物、具有嘧啶环结构的化合物、蒽衍生物、双苯乙烯基苯衍生物、芘衍生物、噁唑衍生物、聚对亚苯基亚乙烯基衍生物等。
发光层可以由主体材料和掺杂材料构成。作为主体材料,优选使用本发明的1,3-二氮杂芴化合物。除此之外,还可以使用mCBP、mCP、噻唑衍生物、苯并咪唑衍生物、聚二烷基芴衍生物、具有吲哚环作为稠合环的部分结构的杂环化合物等。
作为掺杂材料,可以使用芳香族胺衍生物、苯乙烯基胺化合物、硼配合物、荧蒽化合物、金属配合物等。例如,可列举芘衍生物、蒽衍生物、喹吖啶酮、香豆素、红荧烯、苝和它们的衍生物、苯并吡喃衍生物、罗丹明衍生物、氨基苯乙烯基衍生物、螺环双芴衍生物等。它们可以单独地成膜,也可以与其它材料一起混合成膜而成的单层的形式来使用,还可以制成单独成膜而成的层彼此的层叠结构、混合成膜而成的层彼此的层叠结构、或者单独成膜而成的层与混合成膜而成的层的层叠结构。这些材料可以通过蒸镀法、以及旋涂法、喷墨法等公知方法来形成薄膜。
作为本发明的有机电致发光器件的空穴阻挡层,优选使用本发明的1,3-二氮杂芴化合物。除此之外,还可以使用其他具有空穴阻挡性的化合物来形成。例如可以使用2,4,6-三(3-苯基)-1,3,5-三嗪(T2T)、1,3,5-三(1-苯基-1H-苯并咪唑-2-基)苯(TPBi)、浴铜灵(BCP)等菲咯啉衍生物、铝(III)双(2-甲基-8-羟基喹啉)-4-苯基苯酚盐(BAlq)等喹啉醇衍生物的金属络合物、以及各种稀土类络合物、噁唑衍生物、***衍生物、三嗪衍生物等具有空穴阻挡作用的化合物。它们可以单独地成膜,也可以以与其它材料一起混合成膜而成的单层的形式来使用,也可以制成单独成膜而成的层彼此的层叠结构、混合成膜而成的层彼此的层叠结构、或单独成膜而成的层与混合成膜而成的层的层叠结构。这些材料可以通过蒸镀法、以及旋涂法、喷墨法等公知方法来形成薄膜。
上述具有空穴阻挡性的材料也可以用于下述的电子传输层的形成。即,通过使用上述公知的具有空穴阻挡性的材料,可以形成同时作为空穴阻挡层和电子传输层的层。
作为本发明的有机电致发光器件的电子传输层,优选使用本发明的1,3-二氮杂芴化合物。除此之外,还可以使用其他具有电子传输性的化合物形成。例如可以使用Alq3、BAlq为首的羟基喹啉衍生物的金属络合物;各种金属络合物;***衍生物;三嗪衍生物;噁二唑衍生物;吡啶衍生物;双(10-羟基苯并[H]喹啉)铍(Be(bq)2);如2-[4-(9,10-二萘-2-蒽-2-基)苯基]-1-苯基-1H-苯并咪唑(ZADN)等苯并咪唑衍生物;噻二唑衍生物;蒽衍生物;碳二亚胺衍生物;喹喔啉衍生物;吡啶并吲哚衍生物;菲咯啉衍生物;噻咯衍生物等。它们可以单独地成膜,也可以以与其它材料一起混合成膜而成的单层的形式来使用,也可以制成单独成膜而成的层彼此的层叠结构、混合成膜而成的层彼此的层叠结构、或单独成膜而成的层与混合成膜而成的层的层叠结构。这些材料可以通过蒸镀法、以及旋涂法、喷墨法等公知方法来形成薄膜。
作为本发明的有机电致发光器件的电子注入层,可以使用本身公知的材料形成。例如可以使用氟化锂、氟化铯等碱金属盐;氟化镁等碱土金属盐;羟基喹啉锂等羟基喹啉衍生物的金属络合物;氧化铝等金属氧化物等。
在电子注入层或电子传输层中,对于该层中通常使用的材料,可以使用进而N掺杂铯等金属、三芳基氧化膦衍生物等而成的材料。
作为本发明的有机电致发光器件的阴极,优选使用具有低功函数的电极材料如铝、镁,或者具有低功函数的合金如镁银合金、镁铟合金、铝镁合金作为电极材料。
作为本发明的基板,可以使用传统的有机发光器件中的基板,例如玻璃或塑料。在本发明中,选用玻璃基板。
实施例
在以下实施例中对由上述通式(1)表示的化合物及包含其的有机电致发光器件的制造进行具体说明。但是,下述实施例仅用于对本发明进行例示,本发明的范围不限于此。
实施例1:化合物50的合成
(中间体1-1的合成)
中间体1-1的合成路线如下所示:
在50mL单口烧瓶中加入2-茚酮(2.64g,20mmol)和50mL三氯甲烷,在搅拌下滴加N,N-二甲基甲酰胺二甲基缩醛(2.65mL,20mmol)。滴加完毕后,体系继续在室温下反应6小时。反应完毕后,减压蒸去溶剂,得紫色固体2.62g,收率70%。粗品无需进一步纯化直接投入下一步反应中。MS(EI):m/z:187.10[M+]。Anal.calcd for C12H13NO(%):C 76.98,H 7.00,N7.48;found:C 76.95,H 7.03,N 7.46。
向一干燥洁净的100mL单口烧瓶中依次加入甲醇钠(1.51g,28mmol)、4-溴苯甲脒盐酸盐(6.59g,28mmol)和50mL无水乙醇。在不断搅拌下滴加20mL上面步骤的产品(2.62g,14mmol)的无水乙醇溶液,滴加完毕后,体系回流反应3h。待反应结束后,冷却至室温,抽滤除去无机盐,滤饼用少量无水乙醇洗涤。将滤液倒入200mL水中,用1N盐酸中和后用二氯甲烷萃取。滤液经干燥浓缩后得到紫色固体,粗品经乙醇重结晶(活性炭脱色)后得白色固体4.25g,收率70%。MS(EI):m/z:323.08[M+]。Anal.calcd for C17H11BrN2(%):C 63.18,H3.43,N 8.67;found:C 63.15,H 3.46,N 8.66。
(中间体1-2的合成)
中间体1-2的合成路线如下所示:
将中间体1-1(3.23g,10mmol)转移到装有滴液漏斗的100mL三口瓶中,氮气保护下加入100mL四氢呋喃,搅拌溶解,并用冰水浴冷却。在冰浴下加入叔丁醇钠(4.0g,41.7mmol),保持该温度继续搅拌10min后加入碘甲烷(5.9g,41.7mmol)。体系继续搅拌30min后移去冰浴,体系自行升至室温,并于室温下继续反应过夜。反应结束后抽滤除去不溶物,滤液浓缩后经柱层析纯化(石油醚:二氯甲烷=3:1(V/V))后得白色结晶2.88g,收率82%。MS(EI):m/z:351.13[M+]。Anal.calcd for C19H15BrN2(%):C 64.97,H 4.30,N 7.98;found:C 64.96,H 4.34;N 7.95。
(化合物50的合成)
化合物50的合成路线如下所示:
在氮气保护下,在250mL Schlenk瓶中依次加入中间体1-2(1.76g,5mmol)、二(4-联苯基)胺(1.67g,5.2mmol)、醋酸钯(11mg,0.05mmol)、三叔丁基膦四氟硼酸盐(29mg,0.1mmol)、叔丁醇钠(960mg,10mmol)和120mL甲苯,回流搅拌反应12小时。反应完毕,蒸去溶剂,用200mL二氯甲烷溶解残留物,水洗,分出有机层,水层用15mL二氯甲烷萃取两次,合并有机层。蒸去溶剂后,残留物经柱层析分离(石油醚:二氯甲烷=3:1(V/V))。蒸去溶剂,干燥后,得到2.16g白色固体,产率73%。MS(EI):m/z:591.48[M+]。Anal.calcd for C43H33N3(%):C 87.28,H 5.62,N 7.10;found:C 87.25,H 5.65,N 7.08。
实施例2:化合物36的合成
(中间体1-3和1-4的合成)
中间体1-3和1-4的合成路线如下所示:
在50mL单口烧瓶中加入5-溴-2-茚酮(4.22g,20mmol)和50mL三氯甲烷,在搅拌下滴加N,N-二甲基甲酰胺二甲基缩醛(2.65mL,20mmol)。滴加完毕后,体系继续在室温下反应6小时。反应完毕后,减压蒸去溶剂,得紫色固体4.15g,收率78%。粗品包含两种异构体,无需进一步纯化直接投入下一步反应中。MS(EI):m/z:266.02[M+]。Anal.calcd forC12H12BrNO(%):C 54.16,H 4.55,N 5.26;found:C 54.15,H 4.58,N 5.24。
向一干燥洁净的100mL单口烧瓶中依次加入甲醇钠(1.68g,31.2mmol)、苯甲脒盐酸盐(4.90g,31.2mmol)和50mL无水乙醇。在不断搅拌下滴加20mL上面步骤的产品(4.15g,15.6mmol)的无水乙醇溶液,滴加完毕后,体系回流反应3h。待反应结束后,冷却至室温,抽滤除去无机盐,滤饼用少量无水乙醇洗涤。将滤液倒入200mL水中,用1N盐酸中和后用二氯甲烷萃取。滤液经干燥浓缩后得到紫色固体。粗品进一步经柱层析纯化(石油醚:二氯甲烷=2:1(V/V))后得中间体1-3(1.9g)和中间体1-4(1.6g)。中间体1-3,收率38%。MS(EI):m/z:323.10[M+]。Anal.calcd for C17H11BrN2(%):C 63.18,H 3.43,N 8.67;found:C 63.16,H 3.44,N 8.65。中间体1-4,收率32%。MS(EI):m/z:323.02[M+]。Anal.calcd forC17H11BrN2(%):C 63.18,H 3.43,N 8.67;found:C 63.17,H 3.44,N 8.65。
(中间体1-5的合成)
中间体1-5的合成路线如下所示:
将中间体1-3(3.23g,10mmol)转移到装有滴液漏斗的100mL三口瓶中,氮气保护下加入100mL四氢呋喃,搅拌溶解,并用冰水浴冷却。在冰浴下加入叔丁醇钠(4.0g,41.7mmol),保持该温度继续搅拌10min后加入碘甲烷(5.9g,41.7mmol)。体系继续搅拌30min后移去冰浴,体系自行升至室温,并于室温下继续反应过夜。反应结束后抽滤除去不溶物,滤液浓缩后经柱层析纯化(石油醚:二氯甲烷=3:1(V/V))后得白色结晶2.88g,收率76%。MS(EI):m/z:351.08[M+]。Anal.calcd for C19H15BrN2(%):C 64.97,H 4.30,N 7.98;found:C 64.95,H 4.33;N 7.97。
(化合物36的合成)
化合物36的合成路线如下所示:
在氮气保护下,在250mL Schlenk瓶中依次加入中间体1-5(1.7g,5mmol)、二(4-联苯基)胺(1.7g,5.2mmol)、醋酸钯(11mg,0.05mmol)、三叔丁基膦四氟硼酸盐(29mg,0.1mmol)、叔丁醇钠(960mg,10mmol)和120mL甲苯,回流搅拌反应12小时。反应完毕,蒸去溶剂,用200mL二氯甲烷溶解残留物,水洗,分出有机层,水层用15mL二氯甲烷萃取两次,合并有机层。蒸去溶剂后,残留物经柱层析分离(石油醚:二氯甲烷=3:1(V/V))。蒸去溶剂,干燥后,得到2.22g白色固体,产率75%。MS(EI):m/z:591.48[M+]。Anal.calcd for C43H33N3(%):C 87.28,H 5.62,N 7.10;found:C 87.25,H 5.64,N 7.09。
实施例3:化合物41的合成
(中间体1-6的合成)
中间体1-6的合成路线如下所示:
将中间体1-4(3.23g,10mmol)转移到装有滴液漏斗的100mL三口瓶中,氮气保护下加入100mL四氢呋喃,搅拌溶解,并用冰水浴冷却。在冰浴下加入叔丁醇钠(4.0g,41.7mmol),保持该温度继续搅拌10min后加入碘甲烷(5.9g,41.7mmol)。体系继续搅拌30min后移去冰浴,体系自行升至室温,并于室温下继续反应过夜。反应结束后抽滤除去不溶物,滤液浓缩后经柱层析纯化(石油醚:二氯甲烷=3:1(V/V))后得白色结晶2.46g,收率70%。MS(EI):m/z:351.20[M+]。Anal.calcd for C19H15BrN2(%):C 64.97,H 4.30,N 7.98;found:C 64.96,H 4.34;N 7.95。
(化合物41的合成)
化合物41的合成路线如下所示:
在氮气保护下,在250mL Schlenk瓶中依次加入中间体1-6(1.7g,5mmol)、二(4-联苯基)胺(1.7g,5.2mmol)、醋酸钯(11mg,0.05mmol)、三叔丁基膦四氟硼酸盐(29mg,0.1mmol)、叔丁醇钠(960mg,10mmol)和120mL甲苯,回流搅拌反应12小时。反应完毕,蒸去溶剂,用200mL二氯甲烷溶解残留物,水洗,分出有机层,水层用15mL二氯甲烷萃取两次,合并有机层。蒸去溶剂后,残留物经柱层析分离(石油醚:二氯甲烷=3:1(V/V))。蒸去溶剂,干燥后,得到2.31g白色固体,产率78%。MS(EI):m/z:591.52[M+]。Anal.calcd for C43H33N3(%):C 87.28,H 5.62,N 7.10;found:C 87.26,H 5.65,N 7.07。
在本发明中,采用Hatachi F4600荧光分光光度计测量所述化合物41在二氯甲烷溶液中的荧光光谱。
实施例4:有机电致发光器件1(有机EL器件1)的制备
将空穴注入层3、空穴传输层4、电子阻挡层5、发光层6、空穴阻挡层7、电子传输层8、电子注入层9和阴极10依次形成在预先形成为玻璃基板1上的透明阳极2上,以制备如图3所示的有机电致发光器件。
具体地,将形成有膜厚100nm的ITO膜的玻璃基板在Decon 90碱性清洗液中超声处理,去离子水中冲洗,在丙酮和乙醇中各清洗三次,在洁净的环境下烘烤至完全除去水分,用紫外光和臭氧清洗,并用低能阳离子束轰击表面。将该带有ITO电极的玻璃基板置入真空腔内,抽真空至4×10-4-2×10-5Pa。然后在上述带有ITO电极的玻璃基板上以0.2nm/s的蒸镀速率蒸镀2,3,6,7,10,11-六氰基-1,4,5,8,9,12-六氮杂苯并菲(HAT-CN)以形成膜厚为10nm的层作为空穴注入层。在空穴注入层上,以0.2nm/s的蒸镀速率蒸镀N,N'-二苯基-N,N'-(1-萘基)-1,1'-联苯-4,4'-二胺(NPB)以形成膜厚为40nm的层作为空穴传输层。在空穴传输层上,以0.2nm/s的蒸镀速率蒸镀3,3'-二(N-咔唑基)-1,1'-联苯(mCBP)以形成膜厚为10nm的层作为电子阻挡层(EBL)。在电子阻挡层上,以作为主体材料的实施例1的化合物(化合物50)的蒸镀速率为0.2nm/s、作为掺杂材料的GD1的蒸镀速率为0.016nm/s的蒸镀速率进行双源共蒸,形成膜厚为20nm的层作为发光层,GD1的掺杂重量比例为8wt%。在发光层上,以0.2nm/s的蒸镀速率蒸镀铝(III)双(2-甲基-8-羟基喹啉)-4-苯基苯酚盐(BAlq)以形成膜厚为10nm的层作为空穴阻挡层(HBL)。在空穴阻挡层上,以0.2nm/s的蒸镀速率蒸镀BAlq以形成膜厚为40nm的层作为电子传输层(ETL)。在电子传输层上,以0.1nm/s的蒸镀速率蒸镀8-羟基喹啉-锂(Liq)以形成膜厚为2nm的层作为电子注入层。最后,以0.5nm/s以上的蒸镀速率蒸镀铝,形成膜厚为100nm的阴极。
实施例5~6:有机EL器件2~3的制备
除了使用以下表1中的化合物分别代替实施例4的各层中的化合物以外,在以与有机EL器件1相同的条件下制作有机EL器件。
比较例1~2:有机EL器件比较例1~2的制备
除了使用以下表1中的化合物分别代替实施例4的各层中的化合物以外,在以与有机EL器件1相同的条件下制作有机EL器件比较例。
实施例和比较例涉及的化合物结构如下:
表1
在常温下大气中当施加直流电压时,测量实施例4~6中制作的有机EL器件1~3和比较例1~2中制作的有机EL器件比较例1~2的发光特性。测量结果示于表2中。
器件的电流-亮度-电压特性是由带有校正过的硅光电二极管的Keithley源测量系(Keithley 2400Sourcemeter、Keithley 2000Currentmeter)完成的,电致发光光谱是由Photo research公司PR655光谱仪测量的,器件的外部量子效率通过文献Adv.Mater.,2003,15,1043–1048的方法计算可得。
器件寿命的测定为:将发光开始时的发光亮度(初始亮度)设定为10000cd/m2,进行恒定电流驱动直到发光亮度衰减到9500cd/m2(对应于95%,其中初始亮度取作100%:95%衰减)的时间。以GD1作为掺杂剂的器件寿命是指以10000cd/m2为初始亮度,衰减到9500cd/m2(对应于95%,其中初始亮度取作100%:95%衰减)的时间。所有器件均在氮气环境中封装。
表2
由表2可见,本发明的1,3-二氮杂芴化合物获得了优异的性能数据。
有机EL器件比较例2和有机EL器件3采用GD1作为掺杂剂,有机EL器件3的主体材料构成材料为本发明的化合物41。通过器件性能数据的对比可见,有机EL器件3具有更低的工作电压,外部量子效率相对提高了10%以上,器件寿命(95%)也明显要来的更长。
由上可见,本发明的1,3-二氮杂芴化合物相对于现有技术常用的材料可以有效降低工作电压,提高外部量子效率和器件寿命。
本发明的1,3-二氮杂芴化合物具有优异的发光效率和寿命特性、低驱动电压。因此,由该化合物可以制备具有极佳使用寿命的有机电致发光器件。
Claims (10)
1.一种1,3-二氮杂芴化合物,其特征在于,其由下述通式(1)表示:
其中,L1和L2各自独立地表示单键、羰基、具有6至18个碳原子的芳香族烃基或具有5至18个碳原子的芳香族杂环基中的一个或多个;
Ar1~Ar4各自独立地表示任选被一个或多个R1取代的、具有6至30个碳原子的芳香族烃基或任选被一个或多个R1取代的、具有5至30个碳原子的芳香族杂环基中的一个或多个;
X和Y各自独立地表示取代或未取代的具有1至8个碳原子的烷基、取代或未取代的具有6至24个碳原子的芳香族烃基或取代或未取代的具有5至23个碳原子的芳香族杂环基中的一个或多个,或者它们可以连接成环;
m和n各自独立地为0~4的整数,并且m和n不同时为0;
R1表示氢原子、氘原子、氟原子、氯原子、溴原子、碘原子、氰基、NO2、N(R2)2、OR2、SR2、C(=O)R2、P(=O)R2、Si(R2)3、取代或未取代的具有1至20个碳原子的烷基、取代或未取代的具有2至20个碳原子的烯基、取代或未取代的具有2至20个碳原子的炔基、取代或未取代的具有6至40个碳原子的芳香族烃基、或取代或未取代的具有5至40个碳原子的芳香族杂环基中的一个或多个;
R2表示氢原子、氘原子、氟原子、氰基、取代或未取代的具有1至20个碳原子的烷基、取代或未取代的具有6至30个碳原子的芳香族烃基或取代或未取代的具有5至30个碳原子的芳香族杂环基中的一个或多个。
4.根据权利要求1~3中任一项所述的1,3-二氮杂芴化合物,其特征在于,
m和n各自独立地为0~2的整数,并且m和n不同时为0;
L1、L2各自独立地表示单键、羰基、苯基、三嗪基或联苯基中的一个或多个;
X和Y各自独立地表示甲基、乙基、苯基中的一个或多个;或者X和Y可以连接形成螺芴基、螺环三苯胺基、螺环苯基咔唑基或环戊烷基;
R1和R2各自独立地表示苯基、联苯基、三联苯基、四联苯基、五联苯基、苯并噻吩并咔唑、苯并呋喃并咔唑、苯并芴并咔唑、苯并蒽、苯并菲、芴基、螺双芴基、三嗪基、二苯并呋喃基、二苯并噻吩基、咔唑基、N-苯基咔唑基、茚并咔唑基、苯并咪唑基、二苯基-苯并咪唑基、二苯基-噁二唑基、二苯基硼基、三苯基磷氧基、二苯基磷氧基、三苯基硅基或四苯基硅基中的一个或多个。
6.一种电子器件,其特征在于,其包括权利要求1~5中任一项所述的1,3-二氮杂芴化合物。
7.根据权利要求6所述的电子器件,其特征在于,所述电子器件为有机电致发光器件、有机场效应晶体管或有机太阳能电池;
其中,所述有机电致发光器件包括:第一电极、与所述第一电极对置而具备的第二电极、以及夹在所述第一电极与所述第二电极之间的至少一个有机层,所述至少一个有机层包含权利要求1~5中任一项所述的1,3-二氮杂芴化合物。
8.根据权利要求7所述的电子器件,其特征在于,所述至少一个有机层为空穴注入层、空穴传输层、发光层、电子阻挡层、空穴阻挡层或电子传输层。
9.根据权利要求1~5中任一项所述的1,3-二氮杂芴化合物在电子器件中作为发光材料、电子传输材料、电子阻挡材料、空穴注入材料或空穴阻挡材料的用途。
10.根据权利要求9所述的用途,其特征在于,所述电子器件为有机电致发光器件、有机场效应晶体管或有机太阳能电池。
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114292268A (zh) * | 2021-12-10 | 2022-04-08 | 维思普新材料(苏州)有限公司 | 1,3-二氮杂螺芴类衍生物和电子器件 |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104981471A (zh) * | 2013-02-07 | 2015-10-14 | 株式会社Lg化学 | 杂环化合物及使用其的有机发光元件 |
CN104995185A (zh) * | 2013-02-07 | 2015-10-21 | 株式会社Lg化学 | 杂环化合物及使用其的有机发光元件 |
US20170179408A1 (en) * | 2015-12-22 | 2017-06-22 | Samsung Display Co., Ltd. | Condensed cyclic compound and an organic light-emitting device including the same |
KR20180011980A (ko) * | 2016-07-26 | 2018-02-05 | 에스에프씨 주식회사 | 신규한 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
CN107915722A (zh) * | 2016-10-07 | 2018-04-17 | 株式会社Lg化学 | 新型化合物及包含其的有机发光元件 |
KR20190075403A (ko) * | 2017-12-21 | 2019-07-01 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
CN110892539A (zh) * | 2017-07-27 | 2020-03-17 | Sfc株式会社 | 能够低电压驱动且具有高效率、长寿命特性的有机发光元件 |
-
2020
- 2020-07-06 CN CN202010641980.9A patent/CN111718333B/zh active Active
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104981471A (zh) * | 2013-02-07 | 2015-10-14 | 株式会社Lg化学 | 杂环化合物及使用其的有机发光元件 |
CN104995185A (zh) * | 2013-02-07 | 2015-10-21 | 株式会社Lg化学 | 杂环化合物及使用其的有机发光元件 |
US20170179408A1 (en) * | 2015-12-22 | 2017-06-22 | Samsung Display Co., Ltd. | Condensed cyclic compound and an organic light-emitting device including the same |
KR20180011980A (ko) * | 2016-07-26 | 2018-02-05 | 에스에프씨 주식회사 | 신규한 헤테로고리 화합물 및 이를 포함하는 유기 발광 소자 |
CN107915722A (zh) * | 2016-10-07 | 2018-04-17 | 株式会社Lg化学 | 新型化合物及包含其的有机发光元件 |
CN110892539A (zh) * | 2017-07-27 | 2020-03-17 | Sfc株式会社 | 能够低电压驱动且具有高效率、长寿命特性的有机发光元件 |
KR20190075403A (ko) * | 2017-12-21 | 2019-07-01 | 덕산네오룩스 주식회사 | 유기전기 소자용 화합물, 이를 이용한 유기전기소자 및 그 전자 장치 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN114292268A (zh) * | 2021-12-10 | 2022-04-08 | 维思普新材料(苏州)有限公司 | 1,3-二氮杂螺芴类衍生物和电子器件 |
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