CN114456174A - Nitrogen-containing compound, and electronic component and electronic device comprising same - Google Patents
Nitrogen-containing compound, and electronic component and electronic device comprising same Download PDFInfo
- Publication number
- CN114456174A CN114456174A CN202111547507.5A CN202111547507A CN114456174A CN 114456174 A CN114456174 A CN 114456174A CN 202111547507 A CN202111547507 A CN 202111547507A CN 114456174 A CN114456174 A CN 114456174A
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- China
- Prior art keywords
- group
- carbon atoms
- substituted
- unsubstituted
- nitrogen
- Prior art date
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- -1 Nitrogen-containing compound Chemical class 0.000 title claims abstract description 83
- 125000005549 heteroarylene group Chemical group 0.000 claims abstract description 13
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 151
- 239000010410 layer Substances 0.000 claims description 83
- 125000003118 aryl group Chemical group 0.000 claims description 58
- 125000001424 substituent group Chemical group 0.000 claims description 55
- 125000001072 heteroaryl group Chemical group 0.000 claims description 43
- 150000001875 compounds Chemical class 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 20
- 229910052805 deuterium Inorganic materials 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 20
- 125000001624 naphthyl group Chemical group 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 239000002346 layers by function Substances 0.000 claims description 16
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 125000001188 haloalkyl group Chemical group 0.000 claims description 13
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 235000010290 biphenyl Nutrition 0.000 claims description 10
- 239000004305 biphenyl Substances 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000005104 aryl silyl group Chemical group 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 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 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000005110 aryl thio group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000005561 phenanthryl group Chemical group 0.000 claims description 6
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 5
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 3
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 125000005567 fluorenylene group Chemical group 0.000 claims description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 48
- OPDGWSYNXPRREB-UHFFFAOYSA-N 5,6,7,8-tetramethyl-1,2,3,4-tetrahydronaphthalene Chemical compound C1CCCC2=C(C)C(C)=C(C)C(C)=C21 OPDGWSYNXPRREB-UHFFFAOYSA-N 0.000 abstract description 4
- 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 abstract description 4
- 229960005544 indolocarbazole Drugs 0.000 abstract description 4
- 230000005525 hole transport Effects 0.000 description 26
- 230000015572 biosynthetic process Effects 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 18
- 238000002347 injection Methods 0.000 description 16
- 239000007924 injection Substances 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000376 reactant Substances 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 125000002950 monocyclic group Chemical group 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- NLOOVMVNNNYLFS-UHFFFAOYSA-N 6-bromo-1,1,4,4-tetramethyl-2,3-dihydronaphthalene Chemical compound BrC1=CC=C2C(C)(C)CCC(C)(C)C2=C1 NLOOVMVNNNYLFS-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000002950 deficient Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000002386 leaching Methods 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 2
- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 2
- SPSSDDOTEZKOOV-UHFFFAOYSA-N 2,3-dichloroquinoxaline Chemical compound C1=CC=C2N=C(Cl)C(Cl)=NC2=C1 SPSSDDOTEZKOOV-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- MAIALRIWXGBQRP-UHFFFAOYSA-N 9-naphthalen-1-yl-10-naphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(C2=CC3=CC=CC=C3C=C2)=C(C=CC=C2)C2=C1C1=CC=CC2=CC=CC=C12 MAIALRIWXGBQRP-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229920001090 Polyaminopropyl biguanide Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 125000004431 deuterium atom Chemical group 0.000 description 2
- YMWUJEATGCHHMB-DICFDUPASA-N dichloromethane-d2 Chemical compound [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 2
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound 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
- 230000005684 electric field Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 125000004306 triazinyl group Chemical group 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
- HTWMXCZFSCJBEX-UHFFFAOYSA-N 12-phenyl-12,16-diazahexacyclo[11.11.0.02,11.03,8.015,23.017,22]tetracosa-1(13),2(11),3,5,7,9,14,17,19,21,23-undecaene Chemical compound N1C2=CC=CC=C2C2=C1C=C1N(C3=C(C1=C2)C1=C(C=CC=C1)C=C3)C1=CC=CC=C1 HTWMXCZFSCJBEX-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- 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 1
- 241000764238 Isis Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N SnO2 Inorganic materials O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 229910052769 Ytterbium Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 229910052977 alkali metal sulfide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Abstract
The present application relates to a nitrogen-containing compound, and an electronic element and an electronic device comprising the same. The nitrogen-containing compound comprises a structure of indolocarbazole, a nitrogen-containing heteroarylene group and tetramethyltetralin, and when the nitrogen-containing compound is used as a main material of an organic electroluminescent device, the luminous efficiency and the service life of the device can be remarkably improved.
Description
Technical Field
The application relates to the technical field of organic electroluminescent materials, in particular to a nitrogen-containing compound, and an electronic element and an electronic device comprising the same.
Background
With the development of electronic technology and the progress of material science, the application range of electronic components for realizing electroluminescence or photoelectric conversion is more and more extensive. Organic electroluminescent devices, such as Organic Light Emitting Diodes (OLEDs), typically include a cathode and an anode disposed opposite each other, and a functional layer disposed between the cathode and the anode. The functional layer is composed of multiple organic or inorganic film layers, and generally includes an organic light emitting layer, a hole transport layer, an electron transport layer, and the like. When voltage is applied to the anode and the cathode, the two electrodes generate an electric field, electrons on the cathode side move to the electroluminescent layer under the action of the electric field, holes on the anode side also move to the luminescent layer, the electrons and the holes are combined in the electroluminescent layer to form excitons, and the excitons are in an excited state and release energy outwards, so that the electroluminescent layer emits light outwards.
In the conventional organic electroluminescent device, the most important problems are lifetime and efficiency, and as the display has been increased in area, the driving voltage has been increased, and the luminous efficiency and the current efficiency have been increased, so that it is necessary to continuously develop new materials to further improve the performance of the organic electroluminescent device.
Disclosure of Invention
In view of the above problems in the prior art, it is an object of the present invention to provide a nitrogen-containing compound that can be used in an organic electroluminescent device to improve the performance of the device, and an electronic element and an electronic device including the same.
According to a first aspect of the present application, there is provided a nitrogen-containing compound having a structure represented by formula i:
the formula II is connected to any two adjacent positions in the formula I through a connecting bond shown by the letter;
het is a 6-18 membered nitrogen containing heteroarylene group and the Het group contains at least two nitrogen atoms;
L1、L2、L3l are the same or different from each other and are each independently selected from the group consisting of a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar1selected from hydrogen, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; ar (Ar)2Selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;
said L1、L2、L3、L、Ar1、Ar2Wherein the substituents are the same or different and are each independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, a haloalkyi group having 1 to 12 carbon atoms, a haloalkyi group having a halogen atom, a haloalkyi group, a cycloalkyl group, a trialkylsilyl group, a carbon atom, a trialkylsilyl group, a carbon atom, a halogen atom, a groupAryl of 6 to 20, heteroaryl of 3 to 20 carbon atoms, aryloxy of 6 to 20 carbon atoms, arylthio of 6 to 20 carbon atoms, arylsilyl of 6 to 18 carbon atoms, arylphosphono of 12 to 18 carbon atoms; optionally, any two adjacent substituents form a 5-13 membered ring;
R1、R2and R3The same or different from each other, and each is independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an arylthio group having 6 to 20 carbon atoms, an arylsilyl group having 6 to 18 carbon atoms, and an arylphosphono group having 12 to 18 carbon atoms;
n1represents R1Number of (2), n1Selected from 0, 1,2,3 or 4, when n is1When greater than 1, any two R1Identical or different, optionally, any two adjacent R1Forming a ring;
n2represents R2Number of (2), n2Selected from 0, 1 or 2, when n2When greater than 1, any two R2Identical or different, optionally, any two adjacent R2Form a ring of (a);
n3represents R3Number of (2), n3Selected from 0, 1,2,3 or 4, when n is3When greater than 1, any two R3Identical or different, optionally, any two adjacent R3Forming a ring.
According to a second aspect of the present application, there is provided an electronic component comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; the functional layer contains the above-mentioned nitrogen-containing compound.
According to a third aspect of the present application, there is provided an electronic device including the electronic component of the second aspect.
The structure of the nitrogen-containing compound comprises structures of indolocarbazole, nitrogen-containing heteroarylene and tetramethyl tetralin, wherein the indolocarbazole and the tetramethyl tetralin are electron-rich groups and can be used as electron donors (D: donor), the nitrogen-containing heteroarylene is electron-poor groups and is suitable for being used as electron acceptors (A: Acceptor), and the three groups are combined with each other to form a D-A-D structure, so that the dipole moment of a molecule is increased. When the host material has a large dipole moment, it contributes to the host material being oriented parallel to the substrate; meanwhile, the dipole moment of the host material is increased, the interaction between the host material and the guest material is facilitated, the energy transmission efficiency between the host material and the guest material is improved, and the carrier transition dipole moment in the compound is oriented parallel to the substrate, so that the light coupling-out efficiency of the OLED device is improved, and the light emitting efficiency of the device is improved. Therefore, the use of the nitrogen-containing compound of the present application as a host material can significantly improve the light emission efficiency of the device.
Drawings
The accompanying drawings, which are included to provide a further understanding of the application and are incorporated in and constitute a part of this specification, illustrate embodiments of the application and together with the description serve to explain the principles of the application and not to limit the application.
Fig. 1 is a schematic structural view of an organic electroluminescent device according to an embodiment of the present application.
Fig. 2 is a schematic structural diagram of an electronic device according to an embodiment of the present application.
Reference numerals
100. Anode 200, cathode 300, functional layer 310, hole injection layer
320. Hole transport layer 321, first hole transport layer 322, second hole transport layer 330, organic light emitting layer
340. Electron transport layer 350, electron injection layer 400, and electronic device
Detailed Description
Exemplary embodiments will now be described more fully with reference to the accompanying drawings. The exemplary embodiments, however, may be embodied in many different forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of exemplary embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the application.
In a first aspect, the present application provides a nitrogen-containing compound having a structure represented by formula i:
formula II is connected to any two adjacent star positions in formula I through a connecting bond shown by the star;
het is a 6-18 membered nitrogen containing heteroarylene group and the Het group contains at least two nitrogen atoms;
L1、L2、L3l are the same or different from each other and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar1selected from hydrogen, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; ar (Ar)2Selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;
said L1、L2、L3、L、Ar1、Ar2Wherein the substituents are the same or different and are independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an arylthio group having 6 to 20 carbon atoms, an arylsilyl group having 6 to 18 carbon atoms, and an arylphosphono group having 12 to 18 carbon atoms; optionally, optionallyAny two adjacent substituents form a 5-13 membered ring;
R1、R2and R3Identical to or different from each other, and each independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an arylthio group having 6 to 20 carbon atoms, an arylsilyl group having 6 to 18 carbon atoms, and an arylphosphono group having 12 to 18 carbon atoms;
n1represents R1Number of (2), n1Selected from 0, 1,2,3 or 4, when n is1When greater than 1, any two R1Identical or different, optionally, any two adjacent R1Forming a ring;
n2represents R2Number of (2), n2Selected from 0, 1 or 2, when n2When greater than 1, any two R2Identical or different, optionally, any two adjacent R2Form a ring of (a);
n3represents R3Number of (2), n3Selected from 0, 1,2,3 or 4, when n is3When greater than 1, any two R3Identical or different, optionally, any two adjacent R3Forming a ring.
In this application, the terms "optional" and "optionally" mean that the subsequently described event or circumstance may or may not occur. For example, "optionally, any two adjacent substituents form a ring" means that the two substituents may or may not form a ring, i.e., including: a case where two adjacent substituents form a ring and a case where two adjacent substituents do not form a ring. For another example, "optionally, Ar2Wherein any two adjacent substituents form a ring "means Ar2Any two adjacent substituents in (1) may be linked to each other to form a ring, or Ar2Any two adjacent substituents in (1) may also be independent of each otherAre present. "any two adjacent" may include two substituents on the same atom, and may also include two substituents on two adjacent atoms; wherein, when two substituents are present on the same atom, the two substituents may form a saturated or unsaturated spiro ring with the atom to which they are both attached; when two adjacent atoms have a substituent on each, the two substituents may be fused to form a ring.
In the present application, the description that "… … is independently" and "… … is independently" and "… … is independently selected from" are used interchangeably and should be understood broadly, which means that the specific items expressed between the same symbols in different groups do not affect each other, or that the specific items expressed between the same symbols in the same groups do not affect each other. For example,
wherein each q is independently 0, 1,2 or 3, each R "is independently selected from hydrogen, deuterium, fluoro, chloro" and has the meaning: the formula Q-1 represents that Q substituent groups R ' are arranged on a benzene ring, each R ' can be the same or different, and the options of each R ' are not influenced mutually; the formula Q-2 represents that each benzene ring of biphenyl has Q substituent groups R ', the number Q of the substituent groups R' on the two benzene rings can be the same or different, each R 'can be the same or different, and the options of each R' are not influenced with each other.
In the present application, the term "substituted or unsubstituted" means that a functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, the substituent is collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to an aryl group having a substituent Rc or an unsubstituted aryl group. The substituent Rc may be, for example, deuterium, a halogen group, a cyano group, a heteroaryl group, an aryl group, a trialkylsilyl group, an alkyl group, a haloalkyl group, a cycloalkyl group, or the like. The number of substitutions may be 1 or more.
In the present application, "a plurality" means 2 or more, for example, 2,3,4, 5, 6, etc.
In the present application, the number of carbon atoms of the substituted or unsubstituted functional group means all the number of carbon atoms. For example, if L1Is a substituted arylene group having 12 carbon atoms, all of the carbon atoms of the arylene group and the substituents thereon are 12.
In this application, aryl refers to an optional functional group or substituent derived from an aromatic carbon ring. The aryl group can be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group can be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups joined by carbon-carbon bonds, monocyclic and fused ring aryl groups joined by carbon-carbon bonds, two or more fused ring aryl groups joined by carbon-carbon bonds. That is, unless otherwise specified, two or more aromatic groups linked by a carbon-carbon bond can also be considered aryl groups herein. The fused ring aryl group may include, for example, a bicyclic fused aryl group (e.g., naphthyl group), a tricyclic fused aryl group (e.g., phenanthryl group, fluorenyl group, anthracyl group), and the like. The aryl group does not contain a hetero atom such as B, N, O, S, P, Se or Si. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthracyl, phenanthryl, biphenyl, terphenyl, triphenylenyl, perylenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl, phenanthrenyl, pyrenyl,
and the like. In this application, reference to arylene is to a divalent group formed by an aryl group further deprived of a hydrogen atom. In the present application, the number of carbon atoms of the substituted or unsubstituted aryl group may be 6, 10, 12, 13, 14, 15, 16, 17, 18, 20, 25 or 30.
In the present application, the fluorenyl group may be substituted with 1 or more substituents, wherein any adjacent 2 substituents may be combined with each other to form a substituted or unsubstituted spiro ring structure. In the case where the above-mentioned fluorenyl group is substituted, the substituted fluorenyl group may be:
and the like, but is not limited thereto.
In this application, terphenyl comprises
In this application, substituted aryl groups may be aryl groups in which one or more than two hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, -CN, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, haloalkyl groups, deuterated alkyl groups, cycloalkyl groups, arylsilyl groups, and the like. The number of carbon atoms of the substituted aryl group means the total number of carbon atoms of the aryl group and the substituent on the aryl group, for example, the number of carbon atoms of the substituted aryl group having 18 carbon atoms means the total number of carbon atoms of the aryl group and the substituent is 18.
In this application, as L1、L2、L3、L、Ar1And Ar2Aryl groups of substituents of (a), such as, but not limited to, phenyl, naphthyl, phenanthryl, biphenyl, fluorenyl, dimethylfluorenyl, and the like.
In the present application, heteroaryl refers to a monovalent or polyvalent aromatic ring or derivatives thereof containing 1,2,3,4, 5 or 6 heteroatoms in the ring, which may be at least one of B, O, N, P, Si, Se and S. The heteroaryl group may be a monocyclic heteroaryl group or a polycyclic heteroaryl group, in other words, the heteroaryl group may be a single aromatic ring system or a plurality of aromatic ring systems connected by carbon-carbon bonds in a conjugated manner, and any one of the aromatic ring systems is an aromatic monocyclic ring or an aromatic fused ring. Illustratively, heteroaryl groups can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinyl, isoquinolyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, and the like, without being limited thereto. In the present application, the number of carbon atoms of the substituted or unsubstituted heteroaryl group may be selected from 3,4, 5, 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29 or 30.
In this application, as L1、L2、L3、L、Ar1And Ar2Examples of heteroaryl groups as substituents of (a) are, but not limited to, pyridyl, carbazolyl, dibenzothienyl, dibenzofuranyl.
In the present application, substituted heteroaryl groups may be heteroaryl groups in which one or more hydrogen atoms are substituted with groups such as deuterium atoms, halogen groups, -CN, aryl, heteroaryl, trialkylsilyl, alkyl, cycloalkyl, haloalkyl, deuterated alkyl, arylsilyl, and the like. It is understood that the number of carbon atoms in the substituted heteroaryl group refers to the total number of carbon atoms in the heteroaryl group and the substituent on the heteroaryl group.
In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms of the alkyl group may be, for example, 1,2,3,4, 5, 6, 7, 8, 9,10, and specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, and the like.
In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, iodine.
Specific examples of the trialkylsilyl group herein include, but are not limited to, trimethylsilyl group, triethylsilyl group, and the like.
Specific examples of haloalkyl groups in the present application include, but are not limited to, trifluoromethyl.
In the present application, the number of carbon atoms of the cycloalkyl group having 3 to 10 carbon atoms may be, for example, 3,4, 5, 6, 7, 8 or 10. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentyl, cyclohexyl.
In this application, the ring system formed by n atoms is an n-membered ring. For example, phenyl is a 6-membered aryl. A6-to 18-membered nitrogen-containing heteroarylene group means a heteroarylene group having 6 to 18 ring atoms and containing a nitrogen atom in the ring atoms.
In the context of the present application, it is,
as used herein, the term "substituent" refers to a position bonded to another substituent or a bonding position.
As used herein, an delocalized linkage refers to a single bond extending from a ring system
It means that one end of the linkage may be attached to any position in the ring system through which the linkage extends, and the other end to the rest of the compound molecule. For example, as shown in the following formula (f), naphthyl represented by formula (f) is connected with other positions of the molecule through two non-positioned connecting bonds penetrating through a double ring, and the meaning of the naphthyl represented by the formula (f-1) to the formula (f-10) comprises any possible connecting mode shown in the formula (f-1) to the formula (f-10).
As another example, as shown in the following formula (X '), the dibenzofuranyl group represented by formula (X') is attached to another position of the molecule via an delocalized bond extending from the middle of the phenyl ring on one side, which has the meaning shown in any of the possible attachment means as shown in formulas (X '-1) to (X' -4).
In some embodiments of the present application, the nitrogen-containing compound is selected from the structures shown in formulas III-1 and III-2 below:
in some embodiments of the present application, the nitrogen-containing compound is selected from the structures represented by the following formulas III-3:
in some embodiments of the present application, R1、R2And R3Identical to or different from each other and each independently selected from deuterium, fluoro, cyano, trimethylsilyl, trideuteromethyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl or carbazolyl;
n1represents R1Number of (2), n3Selected from 0, 1,2,3 or 4, when n is1When greater than 1, any two R1Identical or different, optionally, any two adjacent R1A benzene ring is formed;
n2represents R2Number of (2), n4Selected from 0, 1 or 2, when n2When greater than 1, any two R2Identical or different, optionally, any two adjacent R2To form a benzene ring;
n3represents R3Number of (2), n5Selected from 0, 1,2,3 or 4, when n is3When greater than 1, any two R3Identical or different, optionally, any two adjacent R3A benzene ring is formed.
In the present application, the nitrogen-containing compound has a structure represented by the structural formula shown below:
in some embodiments of the present application, the nitrogen-containing compound is
Is composed of
In some embodiments herein, Het is a 6-16 membered nitrogen containing heteroarylene group and the Het group contains at least two nitrogen atoms. In other embodiments herein, Het is a 6-membered nitrogen-containing heteroarylene, a 10-membered nitrogen-containing heteroarylene, or a 13-membered nitrogen-containing heteroarylene, and the Het group contains at least two nitrogen atoms.
In some more specific embodiments herein, Het is a 6-to 18-membered electron deficient nitrogen containing heteroaryl (also known as electron deficient heteroaryl) group containing at least two nitrogen atoms in the Het group. Sp on Het2The hybridized nitrogen atom can reduce the electron cloud density of a conjugated system of the heteroaryl instead of improving the electron cloud density of the conjugated system of the heteroaryl on the whole, lone pair electrons on the heteroatom do not participate in the conjugated system, and the electron cloud density of the conjugated system is reduced due to stronger electronegativity of the heteroatom. By way of example, electron deficient heteroaryl groups can include, but are not limited to, triazinyl, pyrimidinyl, quinolinyl, quinoxalinyl, quinazolinyl, isoquinolinyl, benzimidazolyl, benzothiazolyl, benzoxazolyl, phenanthrolinyl, benzoquinazolinyl, phenanthroimidazolyl, benzofuropyrimidinyl, benzothienopyrimidinyl, and the like. The Het group can form an electron transport core group of the compound, so that the compound can effectively realize electron transport, and further can effectively balance the transport rate of electrons and holes in the organic light-emitting layer. Thus, the compound can be used as a bipolar organic light-emitting layer host material for simultaneously transporting electrons and holes, and can also be used as an electron type organic light-emitting layer host material for simultaneously transporting electrons and holesThe organic light-emitting layer is made of a host material.
In some embodiments, Het is selected from the group consisting of:
In some embodiments, Het is selected from the group consisting of:
represents the position of the linkage to the L group3The position at which the group is attached represents the position to which L is attached1The position at which the group is attached; wherein the symbol is not marked, and represents the position to which it is attached
In, L1Is a single bond, Ar1Is hydrogen (i.e.
Is hydrogen).
In some embodiments, Ar1Selected from hydrogen, substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms; ar (Ar)2Selected from substituted or unsubstituted aryl groups having 6 to 25 carbon atoms and substituted or unsubstituted heteroaryl groups having 7 to 18 carbon atoms.
Alternatively, Ar1Selected from hydrogen, substituted or unsubstituted C6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25 or 30The aryl group of (2) is a substituted or unsubstituted heteroaryl group having 12, 13, 14, 15, 16, 17 or 18 carbon atoms.
Alternatively, Ar2Selected from substituted or unsubstituted aryl groups having 6, 7, 8, 9,10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25 or 30 carbon atoms, and substituted or unsubstituted heteroaryl groups having 7, 12, 13, 14, 15, 16, 17, 18 carbon atoms.
Optionally, the Ar is1、Ar2Wherein the substituents are the same or different and are each independently selected from deuterium, halogen, cyano, haloalkyl having 1 to 4 carbon atoms, deuterated alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 12 carbon atoms, heteroaryl having 5 to 12 carbon atoms, trialkylsilyl having 3 to 8 carbon atoms or triphenylsilyl; optionally, any two adjacent substituents form a fluorene ring
In some embodiments, Ar1Selected from the group consisting of hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, and substituted or unsubstituted carbazolyl.
In some embodiments, Ar2Selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, and substituted or unsubstituted benzoxazolyl.
Alternatively, Ar1、Ar2Wherein the substituents are the same or different and are each independently selected from deuterium, fluoro, cyano, trimethylsilyl, triphenylsilylA silicon group, a trideuteromethyl group, a trifluoromethyl group, a cyclopentyl group, a cyclohexyl group, a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a phenyl group, a naphthyl group, a biphenyl group, a pyridyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group.
In some embodiments, Ar1Selected from hydrogen, substituted or unsubstituted groups W1Unsubstituted radical W1Selected from the group consisting of:
substituted radicals W1In (a) has one or more substituents, substituted group W1Wherein the substituents are each independently selected from deuterium, fluoro, cyano, trideuteromethyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothienyl or carbazolyl, and when the group W is1When the number of the substituents is more than 1, the substituents may be the same or different.
In some embodiments, Ar2Selected from substituted or unsubstituted groups W2Unsubstituted radical W2Selected from the group consisting of:
substituted radicals W2In (a) has one or more substituents, substituted group W2Wherein the substituents are each independently selected from deuterium, fluoro, cyano, trideuteromethyl, trimethylsilyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, pyridyl, dibenzofuranyl, dibenzothienyl or carbazolyl, and when the group W is2When the number of the substituents is more than 1, the substituents may be the same or different.
In one embodiment, Ar1Selected from hydrogen or the group consisting of：
In one embodiment, Ar2Selected from the group consisting of:
alternatively, Ar1Selected from hydrogen or the following groups:
alternatively, Ar2Selected from the following groups:
in some embodiments, L1、L2、L3And L are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 7 to 12 carbon atoms.
In some embodiments, L1、L2、L3And L are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 10, 12, 13, 14, 15, 18 carbon atoms, and a substituted or unsubstituted heteroarylene group having 7 or 12 carbon atoms.
Alternatively, L1、L2、L3And the substituents in L are independently selected from deuterium, fluorine, cyano, alkyl with 1-5 carbon atoms, trialkylsilyl with 3-8 carbon atoms, fluoroalkyl with 1-4 carbon atoms and carbon atomDeuterated alkyl with the number of 1-4, aryl with the number of 6-12 carbon atoms and heteroaryl with the number of 5-12 carbon atoms.
Alternatively, L1、L2、L3Each L is independently selected from the group consisting of a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzoxazolyl group;
alternatively, L1、L2、L3The substituents in L are the same or different and are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl or naphthyl.
In some embodiments, L1、L2、L3L is selected from the group consisting of a single bond or the following groups:
in some embodiments, L is selected from a single bond or the following groups:
in some embodiments, L1Selected from a single bond or the following groups:
in some embodiments, L2Each independently selected from a single bond or the following groups:
in some specific embodimentsIn, L3Selected from single bonds or the following groups:
in some more specific embodiments, of formula II
Selected from the group consisting of:
optionally, the nitrogen-containing compound is selected from the group consisting of:
in a second aspect, the present application provides an electronic component comprising an anode, a cathode, and a functional layer disposed between the anode and the cathode; wherein the functional layer comprises a nitrogen-containing compound as described in the first aspect of the present application.
The nitrogen-containing compound provided by the application can be used for forming at least one organic film layer in the functional layer so as to improve the characteristics of the device such as service life and the like.
Optionally, the functional layer comprises an organic light emitting layer comprising the nitrogen containing compound. The organic light-emitting layer may be composed of the nitrogen-containing compound provided herein, or may be composed of the nitrogen-containing compound provided herein and other materials.
Optionally, the electronic element is an organic electroluminescent device.
According to a particular embodiment, the electronic component is an organic electroluminescent device. As shown in fig. 1, the organic electroluminescent device may include an anode 100, a hole injection layer 310, a first hole transport layer 321, a second hole transport layer (hole assist layer) 322, an organic light emitting layer 330, an electron transport layer 340, an electron injection layer 350, and a cathode 200, which are sequentially stacked.
Optionally, the anode 100 comprises an anode material, preferably a material with a large work function that facilitates hole injection into the functional layer. Specific examples of the anode material include metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, Indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metals and oxides, e.g. ZnO: Al or SnO2Sb; or a conductive polymer such as poly (3-methylthiophene), poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline, but are not limited thereto. Preferably, a transparent electrode including Indium Tin Oxide (ITO) as an anode is included.
The functional layer of the organic electroluminescent device further comprises a hole transport layer 320, the hole transport layer 320 being located between the anode and the organic light emitting layer. The hole transport layer includes a first hole transport layer and a second hole transport layer, and the first hole transport layer is closer to the anode than the second hole transport layer.
In the present application, the first hole transport layer 321 may include one or more hole transport materials, and the hole transport layer material may be selected from carbazole multimer, carbazole-linked triarylamine compound, or other types of compounds, and specifically may be selected from the following compounds or any combination thereof:
in one embodiment, the first hole transport layer 321 may be composed of PAPB.
Alternatively, the second hole transport layer 322 may include one or more hole transport materials, and the hole transport material may be selected from carbazole multimer, carbazole-linked triarylamine-based compound, or other types of compounds, which are not specifically limited herein. In one embodiment of the present application, the second hole transport layer 322 is comprised of HT-1.
Optionally, a hole injection layer 310 may be further disposed between the anode 100 and the first hole transport layer 321 to enhance the ability to inject holes into the first hole transport layer 321. The hole injection layer 310 may be made of benzidine derivatives, starburst arylamine compounds, phthalocyanine derivatives, or other materials, which are not limited in this application. The material of the hole injection layer 310 may be selected from, for example, the following compounds or any combination thereof;
in one embodiment of the present application, the hole injection layer 310 is composed of HAT-CN.
Alternatively, the organic light emitting layer 330 may be composed of a single light emitting material, and may also include a host material and a guest material. Alternatively, the organic light emitting layer 330 is composed of a host material and a guest material, and a hole injected into the organic light emitting layer 330 and an electron injected into the organic light emitting layer 330 may be combined in the organic light emitting layer 330 to form an exciton, which transfers energy to the host material, and the host material transfers energy to the guest material, thereby enabling the guest material to emit light.
The guest material of the organic light emitting layer 330 may be a compound having a condensed aryl ring or a derivative thereof, a compound having a heteroaryl ring or a derivative thereof, an aromatic amine derivative, or other materials, which is not particularly limited in the present application. The guest material is also referred to as a dopant material or dopant. They can be classified into fluorescent dopants and phosphorescent dopants according to the type of light emission. For example, specific examples of the red phosphorescent dopant include, but are not limited to,
in another embodiment of the present application, theThe organic electroluminescent device is a red organic electroluminescent device. The host material of the organic light emitting layer 330 may be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, a compound of the present application, a mixture of a compound of the present application and another compound, or another type of material, which is not particularly limited in the present application. In a more specific embodiment, the host material of the organic light-emitting layer 330 is a nitrogen-containing compound of the present application, and the guest material can be, for example, Ir (dmpq)2acac。
The electron transport layer 340 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, which may be selected from, but not limited to, ET-1, LiQ, benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, which is not limited in this application. The material of the electron transport layer 340 includes, but is not limited to, the following compounds:
in one embodiment of the present application, the electron transport layer 340 may be composed of BmPyPhB and LiQ.
In the present application, the cathode 200 may include a cathode material, which is a material having a small work function that facilitates electron injection into the functional layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or a multilayer material such as LiF/Al, Liq/Al, LiO2Al, LiF/Ca, LiF/Al and BaF2and/Ca. Optionally, a metal electrode comprising magnesium and silver is included as a cathode.
Optionally, an electron injection layer 350 may be further disposed between the cathode 200 and the electron transport layer 340 to enhance the ability to inject electrons into the electron transport layer 340. The electron injection layer 350 may include an inorganic material such as an alkali metal sulfide or an alkali metal halide, or may include a complex of an alkali metal and an organic material. In one embodiment of the present application, the electron injection layer 350 may include ytterbium (Yb).
A third aspect of the present application provides an electronic device comprising the electronic component according to the second aspect of the present application.
According to one embodiment, as shown in fig. 2, the electronic device provided is an electronic device 400 comprising the above-described organic electroluminescent device. The electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, which may include, but are not limited to, a computer screen, a mobile phone screen, a television, electronic paper, an emergency light, an optical module, and the like.
The synthesis method of the nitrogen-containing compound of the present application will be specifically described below with reference to the synthesis examples, but the present disclosure is not limited thereto.
Synthetic examples
One skilled in the art will recognize that the chemical reactions described herein may be used to suitably prepare a wide variety of organic compounds of the present application, and that other methods for preparing the compounds of the present application are contemplated as being within the scope of the present application. For example, the synthesis of those non-exemplified compounds according to the present application can be successfully accomplished by those skilled in the art by modification, such as appropriate protection of interfering groups, by the use of other known reagents other than those described herein, or by some routine modification of reaction conditions. Compounds of synthetic methods not mentioned in this application are all commercially available starting products.
1. Synthesis of intermediate Sub-a1
To a 500mL three-necked flask, 6-bromo-1, 1,4, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene (13.36g, 50mmol), 4-chlorobenzeneboronic acid (8.60g, 55mmol), and tetrakis (triphenylphosphine) palladium (Pd (PPh) were added in this order under a nitrogen atmosphere3)40.58g, 0.5mmol), anhydrous sodium carbonate (10.60g, 100mmol), toluene (140mL), tetrahydrofuran (35mL)And deionized water (35mL), stirring and heating are started, the temperature is increased to reflux, and the reaction is carried out for 16 h. After the system was cooled to room temperature, it was extracted with dichloromethane (100mL × 3 times), the organic phases were combined and dried over anhydrous magnesium sulfate, filtered and the solvent was distilled off under reduced pressure to obtain a crude product. Purification by column chromatography on silica gel using n-heptane as the mobile phase gave Sub-a1(13.30g, 89% yield) as a white solid.
Referring to the synthesis of Sub-a1, Sub-a2 was synthesized using reactant a shown in table 1 instead of 4-chlorobenzeneboronic acid.
Table 1: synthesis of Sub-a2
2. Synthesis of intermediate Sub-b1
Under nitrogen atmosphere, 6-bromo-1, 1,4, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene (11.76g, 44mmol), pinacol diboron (12.28g, 48.4mmol), potassium acetate (9.50g, 96.8mmol) and 1, 4-dioxane (120mL) were added in sequence to a 250mL three-necked flask, stirring and heating were started, and when the system was warmed to 40 ℃, tris (dibenzylideneacetone) dipalladium (Pd) was rapidly added2(dba)30.40g, 0.44mmol) and (2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl) (0.42g, 0.88mmol), and the reaction was stirred overnight while continuing to reflux. After the system is cooled to room temperature, adding 200mL of water into the system, fully stirring for 30min, separating out solids, carrying out vacuum filtration, washing a filter cake to be neutral by deionized water, and then leaching by 100mL of absolute ethyl alcohol to obtain gray solids; the crude product was slurried once with n-heptane, then washed with 200mL of toluene, passed through a short pad of silica gel to remove the catalyst, and concentrated to give Sub-b1 as a white solid (16.66g, 83% yield).
With reference to the synthesis of Sub-B1, Sub-B2 and Sub-B3 were synthesized using reactant B shown in table 2 instead of 6-bromo-1, 1,4, 4-tetramethyl-1, 2,3, 4-tetrahydronaphthalene.
Table 2: synthesis of Sub-b2 and Sub-b3
3. Synthesis of intermediate Sub-c1
To a 500mL three-necked flask, under a nitrogen atmosphere, Sub-b1(15.71g, 50mmol), 2, 3-dichloroquinoxaline (14.93g, 75mmol), tetrakis (triphenylphosphine) palladium (Pd (PPh) were added in this order3)40.58g and 0.5mmol), anhydrous sodium carbonate (10.60g and 100mmol), toluene (160mL) and deionized water (40mL), stirring and heating are started, and the temperature is increased to 65-70 ℃ for reaction for 16 h. After the system was cooled to room temperature, it was extracted with dichloromethane (150mL × 3 times), the organic phases were combined and dried over anhydrous magnesium sulfate, filtered, and the filtrate was distilled under reduced pressure to remove the solvent to obtain a crude product. Purification by column chromatography on silica gel using dichloromethane/n-heptane as a mobile phase gave Sub-c1(13.33g, 76% yield) as a white solid.
Referring to the synthesis of Sub-C1, intermediates Sub-C2 to Sub-C12 were synthesized using reactant C instead of Sub-b1 and reactant D instead of 2, 3-dichloroquinoxaline as shown in table 3.
Table 3: synthesis of Sub-c2 to Sub-c12
4. Synthesis of intermediate Sub-d1
Under nitrogen atmosphere, 4-bromobiphenyl (11.65g, 50mmol) and indolo [2,3-A ] are added in sequence into a 250mL three-necked flask]Carbazole (14.10g, 55mmol), tris (dibenzylideneacetone) dipalladium (Pd)2(dba)30.916g, 1mmol), (2-dicyclohexylphosphine-2 ',4',6' -triisopropylbiphenyl) (X-Phos, 0.95g, 2mmol), sodium tert-butoxide (9.61g, 100mmol) and xylene (120mL), heated to reflux and stirred for reaction overnight; after the system is cooled to room temperature, pouring the reaction solution into 250mL of deionized water, fully stirring for 30min, carrying out suction filtration, leaching the filter cake to be neutral by using the deionized water, and leaching by using anhydrous ethanol (200 mL); the filter cake was recrystallized from toluene to give Sub-d1 as a pale green solid (14.70 g; 72% yield).
Referring to the synthesis of Sub-d1, Sub-d2 through Sub-d18 were synthesized using reactant E shown in table 4 instead of 4-bromobiphenyl and reactant F instead of indolo [2,3-a ] carbazole.
Table 4: synthesis of Sub-d2 to Sub-d18
5. Synthesis of Compounds
Synthesis of Compound 1:
to a 250mL three-necked flask, 7, 9-dihydro-7-phenyl-benzo [ G ] was added in sequence under a nitrogen atmosphere]Indolo [2,3-B ]]Carbazole (CAS:1800022-02-9,7.65g, 20mmol), Sub-c1(8.42g, 24mmol), anhydrous potassium carbonate (2.76g, 20mmol), 4-dimethylaminopyridine (1.22g,10mmol) and N, N-dimethylacetamide (80mL), stirring and heating were started, and the temperature was raised to reflux for 16 h. After the system was cooled to room temperature, it was extracted with methylene chloride (100 mL. times.3 times), the organic phases were combined and dried over anhydrous magnesium sulfate,filtering, and distilling the filtrate under reduced pressure to remove the solvent to obtain a crude product. The crude product was recrystallized from toluene to give compound 1 as a white solid (7.53g, 54% yield), M/z 697.3[ M + H ]]+。
Referring to the synthesis procedure of compound 1, the following compound was synthesized using reactant G shown in table 5 instead of 7, 9-dihydro-7-phenyl-benzo [ G ] indolo [2,3-B ] carbazole and reactant H instead of Sub-c 1.
Table 5: synthesis of Compounds of the present application
Compound nuclear magnetic data are shown in the following table:
compound 13 nuclear magnetic:1H-NMR(400MHz,CD2Cl2)δ(ppm)：9.21(s,1H),8.96(d,1H),8.32(d,1H),8.20(d,1H),8.05(d,1H),7.95(d,1H),7.84-7.72(m,4H),7.60-7.26(m,15H),7.17(d,1H),7.11(d,1H),7.02(s,1H),1.56(m,4H),1.12(s,12H)。
preparation and evaluation of an organic electroluminescent device:
embodiments also provide an organic electroluminescent device comprising an anode, a cathode, and an organic layer interposed between the anode and the cathode, the organic layer comprising the organic compound described herein. The organic electroluminescent element of the present application will be described in detail below with reference to examples. However, the following embodiments are merely examples of the present application, and do not limit the present application.
Example 1: preparation of red organic electroluminescent device
The anode was prepared by the following procedure: the thickness of ITO/Ag/ITO is set as
The ITO substrate of (1) was cut into a size of 40mm (length) × 40mm (width) × 0.7mm (thickness), and prepared into an experimental substrate having a cathode, an anode and an insulating layer pattern by using a photolithography process, and UV ozone and O were used2:N2Plasma is used for surface treatment to increase the work function of the anode, and an organic solvent can be used for cleaning the surface of the ITO substrate to remove impurities and oil stains on the surface of the ITO substrate.
HAT-CN was vacuum-deposited on an experimental substrate (anode) to a thickness of
Then depositing PAPB on the hole injection layer by vacuum evaporation to form a layer having a thickness of
The first hole transport layer of (1).
Vacuum evaporating compound HT-1 on the first hole transport layer to a thickness of
The second hole transport layer of (1).
Then, on the second hole transporting layer, compound 1: Ir (dmpq)2acac as 98%: 2% of evaporation rate ratio, and forming a thickness of
The organic light emitting layer (red light emitting layer, R-EML).
On the organic light emitting layer, compounds BmPyPhB and LiQ are mixed at a weight ratio of 1:1 and formed by evaporation
Thick Electron Transport Layer (ETL)) Depositing Yb on the electron transport layer to a thickness of
Then magnesium (Mg) and silver (Ag) were mixed at a rate of 1:9, and vacuum-evaporated on the electron injection layer to form an Electron Injection Layer (EIL) having a thickness of
The cathode of (1).
The thickness of the vacuum deposition on the cathode is set to
Thereby completing the fabrication of the red organic electroluminescent device.
Examples 2 to 41
Organic electroluminescent devices were produced in the same manner as in example 1, except that in the production of the organic light-emitting layer, the compounds in table 6 below were used instead of compound 1 in example 1.
Comparative examples 1 to 2
An organic electroluminescent device was produced in the same manner as in example 1, except that compound a and compound B were used instead of compound 1 in example 1, respectively, in the production of the organic light-emitting layer.
The structural formula of the main material of each functional layer used in the preparation of the organic electroluminescent devices of the above examples and comparative examples is shown below.
The red organic electroluminescent devices prepared in examples 1 to 41 and comparative examples 1 to 2 were tested for their performance at 10mA/cm2The IVL performance of the device is tested under the condition of (1), and the service life of the T95 device is 20mA/cm2Under the conditions of Volt (V) -operating voltage, Cd/A-current efficiency, T95(hrs)—T95The life and the test results are shown in Table 6.
TABLE 6 Performance test results of red organic electroluminescent devices
Referring to table 6 above, it can be seen that when the nitrogen-containing compound of the present application is used as a host material of an organic electroluminescent device, the light-emitting efficiency and the lifetime of the device can be significantly improved. Specifically, the organic electroluminescent devices according to examples 1 to 41 of the present application showed at least 14.2% improvement in efficiency and at least 13.9% improvement in lifetime, as compared with the organic electroluminescent devices according to comparative examples 1 to 2. The reason for this is that indolocarbazoles and tetramethyltetralins are electron-rich groups serving as electron donors (D: donor) and nitrogen-containing heteroarylenes are electron-poor groups serving as electron acceptors, so that D-A-D structures are formed in the molecules, the dipole moment of the molecules is increased, the energy transfer efficiency between host and guest materials is improved, and the dipole moment of carrier transition in the compounds is oriented parallel to the substrate, so that the light coupling-out efficiency of OLED devices is improved, and the efficiency of the devices is improved.
It will be understood by those of ordinary skill in the art that the foregoing embodiments are specific examples for carrying out the present application, and that various changes in form and details may be made therein without departing from the spirit and scope of the present application in practice.
Claims (15)
1. A nitrogen-containing compound having a structure represented by formula i:
formula II is connected to any two adjacent star positions in formula I through a connecting bond shown by the star;
het is a nitrogen-containing heteroarylene group with 6-18 carbon atoms, and the Het group contains at least two nitrogen atoms;
L1、L2、L3l are the same or different from each other and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar1selected from hydrogen, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms; ar (Ar)2Selected from substituted or unsubstituted aryl with 6-30 carbon atoms and substituted or unsubstituted heteroaryl with 3-30 carbon atoms;
said L1、L2、L3、L、Ar1、Ar2Wherein the substituents are the same or different and are independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an arylthio group having 6 to 20 carbon atoms, an arylsilyl group having 6 to 18 carbon atoms, and an arylphosphono group having 12 to 18 carbon atoms; optionally, any two adjacent substituents form a 5-13 membered ring;
R1、R2and R3The same or different from each other, and each is independently selected from deuterium, a halogen group, a cyano group, a haloalkyl group having 1 to 10 carbon atoms, a deuterated alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, a trialkylsilyl group having 3 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, an arylthio group having 6 to 20 carbon atoms, an arylsilyl group having 6 to 18 carbon atoms, and an arylphosphono group having 12 to 18 carbon atoms;
n1represents R1Number of (2), n1Selected from 0, 1,2,3 or 4When n is1When greater than 1, any two R1Identical or different, optionally, any two adjacent R1Forming a ring;
n2represents R2Number of (2), n2Selected from 0, 1 or 2, when n2When greater than 1, any two R2Identical or different, optionally, any two adjacent R2Form a ring of (a);
n3represents R3Number of (2), n3Selected from 0, 1,2,3 or 4, when n is3When greater than 1, any two R3Identical or different, optionally, any two adjacent R3Forming a ring.
2. The nitrogen-containing compound of claim 1, wherein Het is selected from the group consisting of:
3. The nitrogen-containing compound according to claim 1, wherein the nitrogen-containing compound is selected from the structures represented by the following formulae III-1 and III-2:
4. the nitrogen-containing compound according to claim 1, wherein R is1、R2And R3Are identical or different from each otherAnd each is independently selected from deuterium, fluoro, cyano, trimethylsilyl, trideuteromethyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl;
n1represents R1Number of (2), n3Selected from 0, 1,2,3 or 4, when n is1When greater than 1, any two R1Identical or different, optionally, any two adjacent R1A benzene ring is formed;
n2represents R2Number of (2), n4Selected from 0, 1 or 2, when n2When greater than 1, any two R2Identical or different, optionally, any two adjacent R2To form a benzene ring;
n3represents R3Number of (2), n5Selected from 0, 1,2,3 or 4, when n is3When greater than 1, any two R3Identical or different, optionally, any two adjacent R3A benzene ring is formed.
5. The nitrogen-containing compound according to claim 1, wherein the Ar is1Selected from hydrogen, substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 12 to 18 carbon atoms;
optionally, the Ar is2Selected from substituted or unsubstituted aryl with 6-25 carbon atoms and substituted or unsubstituted heteroaryl with 7-18 carbon atoms;
optionally, the Ar is1、Ar2Wherein the substituents are the same or different and are each independently selected from deuterium, halogen, cyano, haloalkyl having 1 to 4 carbon atoms, deuterated alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 12 carbon atoms, heteroaryl having 5 to 12 carbon atoms, trialkylsilyl having 3 to 8 carbon atoms or triphenylsilyl; optionally, any two adjacent substituents form a fluorene ring.
6. The nitrogen-containing compound according to claim 1, wherein Ar is Ar1Selected from the group consisting of hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl;
Ar2selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted terphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirobifluorenyl, substituted or unsubstituted phenanthrenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted benzoxazolyl;
alternatively, Ar1、Ar2The substituents in (a) are the same or different and are each independently selected from deuterium, fluoro, cyano, trimethylsilyl, triphenylsilyl, trideuteromethyl, trifluoromethyl, cyclopentyl, cyclohexyl, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl, biphenyl, pyridyl, dibenzofuranyl, dibenzothienyl, or carbazolyl.
7. The nitrogen-containing compound according to claim 1, wherein Ar is Ar1Selected from hydrogen or the group consisting of:
Ar2selected from the group consisting of:
8. the compound of claim 1 containing nitrogenObject of, wherein L1、L2、L3L are the same or different from each other and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroarylene group having 7 to 12 carbon atoms;
alternatively, L1、L2、L3And the substituents in L are independently selected from deuterium, fluorine, cyano, alkyl with 1-4 carbon atoms, trialkylsilyl with 3-8 carbon atoms, fluoroalkyl with 1-4 carbon atoms, deuterated alkyl with 1-4 carbon atoms, aryl with 6-12 carbon atoms and heteroaryl with 5-12 carbon atoms.
9. The nitrogen-containing compound according to claim 1, wherein L1、L2、L3L are the same or different from each other and are each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted fluorenylene group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted benzoxazolyl group;
alternatively, L1、L2、L3The substituents in L are the same or different and are each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, tert-butyl, trifluoromethyl, trideuteromethyl, trimethylsilyl, phenyl or naphthyl.
10. The nitrogen-containing compound according to claim 1, wherein L1、L2、L3L is selected from the group consisting of a single bond or the following groups:
11. the nitrogen-containing compound of claim 1, wherein Het is selected from the group consisting of:
represents the position of the linkage to the L group3The position at which the group is attached represents the position to which L is attached1The position to which the group is attached, not marked in the formula, represents the position to which the group is attached
In, L1Is a single bond, Ar1Is hydrogen.
12. The nitrogen-containing compound of claim 1, wherein the nitrogen-containing compound is selected from the group consisting of:
13. an electronic component comprising an anode and a cathode disposed opposite to each other, and a functional layer disposed between the anode and the cathode; characterized in that the functional layer comprises the nitrogen-containing compound according to any one of claims 1 to 12.
14. The electronic element according to claim 13, wherein the functional layer comprises an organic light-emitting layer containing the nitrogen-containing compound;
optionally, the electronic element is an organic electroluminescent device, and the organic light-emitting layer contains the nitrogen-containing compound.
15. An electronic device, characterized by comprising the electronic component of claim 13 or 14.
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| WO2023221048A1 (en) * | 2022-05-19 | 2023-11-23 | 京东方科技集团股份有限公司 | Light-emitting material and light-emitting device |
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