CN111072659A - Compound, organic electroluminescent device, and electronic device - Google Patents
Compound, organic electroluminescent device, and electronic device Download PDFInfo
- Publication number
- CN111072659A CN111072659A CN201911369556.7A CN201911369556A CN111072659A CN 111072659 A CN111072659 A CN 111072659A CN 201911369556 A CN201911369556 A CN 201911369556A CN 111072659 A CN111072659 A CN 111072659A
- Authority
- CN
- China
- Prior art keywords
- carbon atoms
- independently selected
- group
- substituted
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 74
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 225
- 125000003118 aryl group Chemical group 0.000 claims abstract description 63
- 239000000463 material Substances 0.000 claims abstract description 53
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 41
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 39
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 18
- 239000000126 substance Substances 0.000 claims abstract description 14
- 125000000732 arylene group Chemical group 0.000 claims abstract description 12
- 125000005549 heteroarylene group Chemical group 0.000 claims abstract description 11
- 239000010410 layer Substances 0.000 claims description 77
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
- 229910052799 carbon Inorganic materials 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 239000012044 organic layer Substances 0.000 claims description 16
- 229910052805 deuterium Inorganic materials 0.000 claims description 12
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052710 silicon Inorganic materials 0.000 claims description 9
- 125000005110 aryl thio group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000005104 aryl silyl group Chemical group 0.000 claims description 4
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 abstract description 4
- 230000007704 transition Effects 0.000 abstract description 3
- 238000005516 engineering process Methods 0.000 abstract description 2
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 abstract 1
- 230000002035 prolonged effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 132
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 37
- 239000000543 intermediate Substances 0.000 description 34
- 238000003756 stirring Methods 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 239000012074 organic phase Substances 0.000 description 23
- 239000002994 raw material Substances 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 238000002347 injection Methods 0.000 description 18
- 239000007924 injection Substances 0.000 description 18
- -1 aluminum 8-hydroxyquinoline Chemical compound 0.000 description 16
- 238000001035 drying Methods 0.000 description 16
- 238000010438 heat treatment Methods 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 12
- 230000000903 blocking effect Effects 0.000 description 12
- 239000007791 liquid phase Substances 0.000 description 12
- 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 12
- 238000010992 reflux Methods 0.000 description 12
- 239000007858 starting material Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 238000012544 monitoring process Methods 0.000 description 9
- 239000011343 solid material Substances 0.000 description 9
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 8
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 125000002950 monocyclic group Chemical group 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 6
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 230000021615 conjugation Effects 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 229910052702 rhenium Inorganic materials 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- JAZNSOPOXXXZQO-UHFFFAOYSA-N [N].CCO Chemical compound [N].CCO JAZNSOPOXXXZQO-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 125000001725 pyrenyl group Chemical group 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- MINMDCMSHDBHKG-UHFFFAOYSA-N 4-[4-[[6-methoxy-2-(2-methoxyimidazo[2,1-b][1,3,4]thiadiazol-6-yl)-1-benzofuran-4-yl]oxymethyl]-5-methyl-1,3-thiazol-2-yl]morpholine Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(=C(S1)C)N=C1N1CCOCC1 MINMDCMSHDBHKG-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 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
- 239000010405 anode material Substances 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- 150000004866 oxadiazoles Chemical class 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 2
- 125000005561 phenanthryl group Chemical group 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
- 238000002360 preparation method Methods 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- AFVDZBIIBXWASR-AATRIKPKSA-N (E)-1,3,5-hexatriene Chemical compound C=C\C=C\C=C AFVDZBIIBXWASR-AATRIKPKSA-N 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- BRMRAJNUAMLZGO-UHFFFAOYSA-N 2,3-dimethyl-6-phenylnaphthalene Chemical compound C1=C2C=C(C)C(C)=CC2=CC=C1C1=CC=CC=C1 BRMRAJNUAMLZGO-UHFFFAOYSA-N 0.000 description 1
- UIPSRNHDSBVXHY-UHFFFAOYSA-N 2,5-dichloropyridine-4-carbaldehyde Chemical compound ClC1=CC(C=O)=C(Cl)C=N1 UIPSRNHDSBVXHY-UHFFFAOYSA-N 0.000 description 1
- AWXGSYPUMWKTBR-UHFFFAOYSA-N 4-carbazol-9-yl-n,n-bis(4-carbazol-9-ylphenyl)aniline Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(N(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 AWXGSYPUMWKTBR-UHFFFAOYSA-N 0.000 description 1
- DIVZFUBWFAOMCW-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n,1-n-bis[4-(n-(3-methylphenyl)anilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 DIVZFUBWFAOMCW-UHFFFAOYSA-N 0.000 description 1
- QRXMUCSWCMTJGU-UHFFFAOYSA-N 5-bromo-4-chloro-3-indolyl phosphate Chemical compound C1=C(Br)C(Cl)=C2C(OP(O)(=O)O)=CNC2=C1 QRXMUCSWCMTJGU-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [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 group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-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
- 101000837344 Homo sapiens T-cell leukemia translocation-altered gene protein Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 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
- 229910002666 PdCl2 Inorganic materials 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
- XOLBLPGZBRYERU-UHFFFAOYSA-N SnO2 Inorganic materials O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 102100028692 T-cell leukemia translocation-altered gene protein Human genes 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-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
- 125000002723 alicyclic group Chemical group 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
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 1
- 125000001769 aryl amino group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910001632 barium fluoride Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- UNXISIRQWPTTSN-UHFFFAOYSA-N boron;2,3-dimethylbutane-2,3-diol Chemical compound [B].[B].CC(C)(O)C(C)(C)O UNXISIRQWPTTSN-UHFFFAOYSA-N 0.000 description 1
- 125000000707 boryl group Chemical group B* 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000001975 deuterium Chemical group 0.000 description 1
- 125000004431 deuterium atom Chemical group 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000009740 moulding (composite fabrication) Methods 0.000 description 1
- GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- MHJUNMARMFAUBI-UHFFFAOYSA-N n-phenyliminobenzamide Chemical compound C=1C=CC=CC=1C(=O)N=NC1=CC=CC=C1 MHJUNMARMFAUBI-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000005649 substituted arylene group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000004587 thienothienyl group Chemical group S1C(=CC2=C1C=CS2)* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- 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
-
- 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
- H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
-
- 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
-
- 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
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
-
- 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
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
-
- 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
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- 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
-
- 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
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
-
- 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
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present application belongs to the field of OLED technology and provides a compound having a structure represented by chemical formula 1: wherein, X1、X2、X3、X4、X5And X6Each independently selected from a C atom or a N atom, and X1、X2、X3And only one is an N atom, X4、X5And X6And only one of them is an N atom; l is1And L2Each independently selected fromA bond, C1-C20 alkylene, C3-C20 cycloalkylene, C6-C30 arylene, C3-C30 heteroarylene; ar (Ar)1And Ar2Each independently selected from C1-C20 alkyl, C3-C20 cycloalkyl, C6-C30 aryl, C3-C30 heteroaryl, Si (R)1R2R3). The application provides a compound using phenanthrene fused ring derivatives as a parent nucleus, wherein molecules of the compound have strong plane ductility, the rigidity of the material can be enhanced, and the service life of the compound can be prolonged. In addition, a plurality of nitrogen atom centers exist in molecules at the same time, the density of electron clouds in the molecules is increased, the electron mobility and the transition rate can be improved, and the organic electroluminescent device has high device efficiency. The application also provides an organic electroluminescent device and an electronic device.
Description
Technical Field
The application relates to the technical field of organic materials, in particular to a condensed ring compound, an organic electroluminescent device comprising the condensed ring compound and an electronic device comprising the condensed ring compound.
Background
An organic light-emitting diode (OLED) is simply referred to as an OLED. The principle is that when an electric field is applied to the anode and the cathode, holes on the anode side and electrons on the cathode side move to the light emitting layer and are combined to form excitons in the light emitting layer, the excitons are in an excited state and release energy outwards, and the excitons emit light outwards in the process of changing the energy released from the excited state to the energy released from the ground state. Since Kodak corporation reports electroluminescence of organic molecules in 1987 and Cambridge university in England reports electroluminescence of polymers in 1990, various countries in the world have developed research and development. The material has the advantages of simple structure, high yield, low cost, active luminescence, high response speed, high fraction and the like, and has the performances of low driving voltage, full solid state, no vacuum, oscillation resistance, low temperature (-40 ℃) resistance and the like. In recent years, the OLED material has been widely used in the field of smart phones, is considered as a new technology that is most likely to replace liquid crystal displays in the future, and has attracted great attention. The organic charge transport material is an organic semiconductor material which can realize the controllable directional ordered migration of carriers under the action of an electric field when the carriers (electrons or holes) are injected, thereby realizing charge transport. Compared with inorganic materials, the organic charge transport material has the advantages of low cost, low toxicity, easy processing and forming, chemical modification to meet different requirements, capability of manufacturing fully flexible devices and the like, and can be divided into organic hole transport (p-type) materials and organic electron transport (n-type) materials. N-type materials have evolved more slowly than organic p-type materials, such as aluminum 8-hydroxyquinoline (Alq3) and the oxadiazole derivative PBD, which were studied earlier.
Efficient commercial organic light emitting diodes employ phosphors containing organometallic iridium complexes because they can trap both singlet and triplet excitons, thereby achieving 100% internal quantum efficiency. However, since the excited exciton lifetime of the transition metal complex is relatively too long and the concentration quenching effect of the light emitting material is easily generated, the unwanted triplet-triplet (T1-T1) is quenched in the practical operation of the device, and in order to overcome this problem, researchers often dope the triplet light emitting guest material into the organic light emitting host material. In recent years, highly efficient phosphorescent devices have been few, mainly due to the lack of guest materials having both good carrier transport properties and high triplet energy levels.
The information disclosed in the background section is only for enhancement of understanding of the background of the application and therefore it may contain information that does not constitute prior art that is known to a person of ordinary skill in the art.
Disclosure of Invention
The present application aims to provide a photoelectric material applied to an organic electroluminescent diode (OLED) and an application thereof in an electroluminescent device, so that the photoelectric material has the advantages of excellent photoelectric performance, high efficiency, low driving voltage and long service life.
In order to achieve the purpose, the following technical scheme is adopted in the application.
The present application provides a nitrogen heterocyclic compound having a structure represented by chemical formula 1:
wherein, X1、X2、X3、X4、X5And X6Each independently selected from a C atom or a N atom, and X1、X2、X3And only one is an N atom, X4、X5And X6And only one of them is an N atom;
L1and L2Each independently selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar1and Ar2Each independently selected from substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and Si (R)1R2R3)；
R1，R2，R3Each independently selected from the following substituted or unsubstituted groups: an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 30 carbon atoms.
The application provides a phenanthrene fused ring derivative as a parent nucleus, and a compound molecule has strong planarity. The strong plane ductility of the compound molecules can enhance the rigidity of the material and prolong the service life of the material. In addition, a large conjugated system is easily formed by the molecular parent nucleus and the aryl/heteroaryl, a plurality of nitrogen atom centers exist at the same time, the density of electron clouds in molecules is increased, the HOMO energy level can be further adjusted to a proper level, the electron mobility and the transition rate are further improved, and the organic electroluminescent device has high device efficiency.
The present application also provides an organic electroluminescent device and an electronic device including the compound.
Drawings
FIG. 1 is a general chemical formula of a compound of the present application;
FIG. 2 is a schematic structural view of one embodiment of an organic electroluminescent device of the present application;
fig. 3 is a schematic view of an electronic device using the organic electroluminescent device of the present application.
Reference numerals:
100-an anode; 200-a cathode; 300-organic layer; 310-a hole injection layer; 320-a hole transport layer; 330-electron blocking layer; 340-an organic electroluminescent layer; 350-a hole blocking layer; 360-electron transport layer; 370-an electron injection layer; 400-electronic device.
Detailed Description
Example embodiments will now be described more fully with reference to the accompanying drawings. Example embodiments may, however, 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 example 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. One skilled in the relevant art will recognize, however, that the subject matter of the present application can be practiced without one or more of the specific details, or with other methods, materials, devices, etc. In other instances, well-known technical solutions have not been shown or described in detail to avoid obscuring aspects of the present application. The same reference numerals in the drawings denote the same or similar structures, and thus their detailed description will be omitted.
Furthermore, the drawings are merely schematic illustrations of the present application and are not necessarily drawn to scale. The same reference numerals in the drawings denote the same or similar parts, and thus their repetitive description will be omitted. The terms "a" and "the" are used to indicate the presence of one or more elements/components/etc.; the terms "comprising" and "having" are intended to be inclusive and mean that there may be additional elements/components/etc. other than the listed elements/components/etc.
The technical solution of the present application will be described in detail below.
One aspect of the present application provides a compound having a structure represented by chemical formula 1:
wherein the content of the first and second substances,X1、X2、X3、X4、X5and X6Each independently selected from a C atom or a N atom, and X1、X2、X3And only one is an N atom, X4、X5And X6And only one of them is an N atom;
L1and L2Each independently selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar1and Ar2Each independently selected from the following substituted or unsubstituted groups: alkyl group having 1 to 20 carbon atoms, cycloalkyl group having 3 to 20 carbon atoms, aryl group having 6 to 30 carbon atoms, heteroaryl group having 3 to 30 carbon atoms, Si (R)1R2R3)。
R1，R2，R3Each independently selected from the following substituted or unsubstituted groups: alkyl with 1-20 carbon atoms and aryl with 6-30 carbon atoms;
said L1And L2、Ar1And Ar2The substituents are the same or different and are each independently selected from deuterium, halogen, cyano, alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, alkylthio having 1 to 12 carbon atoms, haloalkyl having 1 to 12 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, aryloxy having 6 to 18 carbon atoms, arylthio having 6 to 18 carbon atoms, aryl having 6 to 18 carbon atoms, heteroaryl having 3 to 18 carbon atoms and arylsilyl having 6 to 24 carbon atoms.
In the present application, L1、L2、Ar1And Ar2The number of carbon atoms of (b) means all the number of carbon atoms. For example, if L1Selected from the group consisting of substituted arylene groups having 12 carbon atoms, all of the carbon atoms of the arylene group and the substituents thereon are 12.
In the present application, when a specific definition is not otherwise provided, "hetero" means that at least 1 hetero atom of B, N, O, S or P or the like is included in one functional group and the remaining atoms are carbon and hydrogen. An unsubstituted alkyl group can be a "saturated alkyl group" without any double or triple bonds.
In this application, the terms "optional" or "optionally" mean that the subsequently described event or circumstance may, but need not, occur, and that the description includes instances where the event or circumstance occurs or does not. For example, "a heterocyclic group optionally substituted with an alkyl" means that an alkyl may, but need not, be present, and the description includes the scenario where the heterocyclic group is substituted with an alkyl and the scenario where the heterocyclic group is not substituted with an alkyl. "optionally, Re and Rf attached to the same atom may be linked to each other to form a saturated or unsaturated 5-to 10-membered aliphatic ring" means that Re and Rf attached to the same atom may be, but need not be, cyclic, including the case where Re and Rf are linked to each other to form a saturated or unsaturated 5-to 10-membered aliphatic ring, and also including the case where Re and Rf are present independently of each other.
In the present application, the descriptions "… … is independently" and "… … is independently" and "… … is independently selected from" are interchangeable, and should be understood in a broad sense, which means that the specific items expressed between the same symbols do not affect each other in different groups, or that the specific items expressed between the same symbols do not affect each other in the same groups. 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 either no substituent or substituted with one or more substituents. Such substituents include, but are not limited to, deuterium (D), halogen groups (F, Cl, Br), cyano, alkyl, alkenyl, alkynyl, haloalkyl, aryl, heteroaryl, aryloxy, arylthio, cycloalkyl, heterocycloalkyl.
In the present application, "alkyl" may include straight chain alkyl or branched alkyl. Alkyl groups may have 1 to 20 carbon atoms, and in the present application, numerical ranges such as "1 to 20" refer to each integer in the given range. For example, "1 to 20 carbon atoms" refers to an alkyl group that may include 1 carbon atom, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms, 11 carbon atoms, 12 carbon atoms, 13 carbon atoms, 14 carbon atoms, 15 carbon atoms, 16 carbon atoms, 17 carbon atoms, 18 carbon atoms, 19 carbon atoms, or 20 carbon atoms. The alkyl group can also be a medium size alkyl group having 1 to 10 carbon atoms. The alkyl group may also be a lower alkyl group having 1 to 6 carbon atoms. Further, the alkyl group may be substituted or unsubstituted.
Alternatively, the alkyl group is selected from alkyl groups having 1 to 10 carbon atoms, and specific examples include, but are not limited to, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, and hexyl.
In the present application, "alkenyl" refers to a hydrocarbon group comprising one or more double bonds in a straight or branched hydrocarbon chain. Alkenyl groups may be unsubstituted or substituted. An alkenyl group can have 1 to 20 carbon atoms, and whenever appearing herein, a numerical range such as "1 to 20" refers to each integer in the given range. For example, "1 to 20 carbon atoms" refers to an alkenyl group that may contain 1 carbon atom, 2 carbon atoms, 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms, 11 carbon atoms, 12 carbon atoms, 13 carbon atoms, 14 carbon atoms, 15 carbon atoms, 16 carbon atoms, 17 carbon atoms, 18 carbon atoms, 19 carbon atoms, or 20 carbon atoms. For example, the alkenyl group can be vinyl, butadiene, or 1,3, 5-hexatriene.
In the present application, cycloalkyl refers to a saturated hydrocarbon containing an alicyclic structure, including monocyclic and fused ring structures. Cycloalkyl groups may have 3-20 carbon atoms, and numerical ranges such as "3 to 20" refer to each integer in the given range. For example, "3 to 20 carbon atoms" refers to a cycloalkyl group that can include 3 carbon atoms, 4 carbon atoms, 5 carbon atoms, 6 carbon atoms, 7 carbon atoms, 8 carbon atoms, 9 carbon atoms, 10 carbon atoms, 11 carbon atoms, 12 carbon atoms, 13 carbon atoms, 14 carbon atoms, 15 carbon atoms, 16 carbon atoms, 17 carbon atoms, 18 carbon atoms, 19 carbon atoms, or 20 carbon atoms. The cycloalkyl group may be a small ring, a normal ring or a large ring having 3 to 20 carbon atoms. Cycloalkyl groups can also be divided into monocyclic-only one ring, bicyclic-two rings, polycyclic-three or more rings. Cycloalkyl groups can also be divided into spiro rings, fused rings, and bridged rings, in which two rings share a common carbon atom, and more than two rings share a common carbon atom. In addition, cycloalkyl groups may be substituted or unsubstituted.
Alternatively, the cycloalkyl group is selected from cycloalkyl groups having 3 to 10 carbon atoms, and specific examples include, but are not limited to, cyclopropane, cyclobutane, cyclopentane, cyclohexane, and adamantane.
In the present application, aryl refers to an optional functional group or substituent derived from an aromatic hydrocarbon ring. The aryl group may be a monocyclic aryl group or a polycyclic aryl group, in other words, the aryl group may be a monocyclic aryl group, a fused ring aryl group, two or more monocyclic aryl groups connected by carbon-carbon bond conjugation, a monocyclic aryl group and a fused ring aryl group connected by carbon-carbon bond conjugation, two or more fused ring aryl groups connected by carbon-carbon bond conjugation. That is, two or more aromatic groups conjugated through a carbon-carbon bond may also be considered as an aryl group in the present application. Wherein the aryl group does not contain a heteroatom such as B, N, O, S or P. For example, biphenyl, terphenyl, and the like are aryl groups in this application. Examples of the aryl group may include phenyl, naphthyl, fluorenyl, anthracyl, phenanthryl, biphenyl, terphenyl, quaterphenyl, pentabiphenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, benzofluoranthenyl, phenanthrenyl, pyrenyl, phenanthrenyl, pyrenyl,
a phenyl group, a fluorenyl group, and the like, without being limited thereto. An "aryl" group herein may contain from 6 to 30 carbon atoms, in some embodiments the number of carbon atoms in the aryl group may be from 6 to 25, in other embodiments the number of carbon atoms in the aryl group may be from 6 to 18, and in other embodiments the number of carbon atoms in the aryl group may be from 6 to 13. For example, the number of carbon atoms may be 6, 12, 13, 18, 20, 25 or 30, and of course, other numbers may be used, which are not listed here.
In the present application, the aryl group having 6 to 25 ring-forming carbon atoms means that the number of carbon atoms located on the aromatic ring in the aryl group is 6 to 25, and the number of carbon atoms in the substituent on the aryl group is not counted. The number of cyclic carbon atoms in the aryl group may be 6 to 25, 6 to 20, 6 to 18, 6 to 14, or 6 to 10, but is not limited thereto.
In this application, substituted aryl refers to an aryl group in which one or more hydrogen atoms are replaced with another group. For example, at least one hydrogen atom is substituted with deuterium atoms, F, Cl, I, CN, hydroxyl, amino, branched alkyl, straight chain alkyl, cycloalkyl, alkoxy, alkylamino, or other groups. It is understood that a substituted aryl group having 18 carbon atoms refers to an aryl group and the total number of carbon atoms in the substituents on the aryl group being 18. For example, 2, 3-dimethyl-6-phenylnaphthalene has a carbon number of 18, 9, 9-diphenylfluorenyl group of 25. Among them, biphenyl can be interpreted as an aryl group or a substituted phenyl group.
In the present application, the fluorenyl group may be substituted and two substituents may be combined with each other to form a spiro structure, and specific examples include, but are not limited to, the following structures:
in the present application, the heteroaryl group may be a heteroaryl group including at least one of B, O, N, P, Si and S as a heteroatom. 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. For example, heteroaryl groups can include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolyl, indolyl, carbazolyl, N-arylcarbazolyl, N-heteroarylcarbazolyl, N-alkylcarbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothienyl, thienothienyl, benzofuryl, phenanthrolinyl, isoxazolyl, thiadiazolyl, benzothiazolyl, phenothiazinyl, dibenzosilyl, dibenzofuryl, phenyl-substituted dibenzofuryl, Dibenzofuranyl-substituted phenyl groups, and the like, without being limited thereto. Wherein, thienyl, furyl, phenanthroline and the like are heteroaryl of a single aromatic ring system, and N-aryl carbazolyl, N-heteroaryl carbazolyl, phenyl-substituted dibenzofuryl and the like are heteroaryl of a plurality of aromatic ring systems connected by carbon-carbon bond conjugation.
The heteroaryl group having a carbon number of 3 to 24 as a ring-forming carbon means that the number of carbon atoms located on the heteroaryl ring in the heteroaryl group is 3 to 24, and the number of carbon atoms in the substituent on the heteroaryl group is not counted. The number of carbon atoms on the heteroaryl group may be 3-24, 3-18, 4-18, 3-12, 3-8, but is not limited thereto.
In this application, substituted heteroaryl refers to heteroaryl groups in which one or more hydrogen atoms are replaced by a group thereof, for example at least one hydrogen atom is replaced by a deuterium atom, F, Cl, Br, CN, amino, alkyl, haloalkyl, cycloalkyl, aryloxy, arylthio, silyl, alkylamino, arylamino, boryl, phosphino, or other group.
In this application, the explanation for aryl applies to arylene and the explanation for heteroaryl applies equally to heteroarylene.
In the present application, the halogen may be a fluorine atom, a chlorine atom, a bromine atom, an iodine atom.
In some embodiments, the compound of formula 1 described herein is selected from the following compounds:
wherein, X1、X2、X3、X4、X5And X6Each independently selected from a C atom or a N atom, and X1、X2、X3And only one is an N atom, X4、X5And X6And only one of them is an N atom.
Alternatively, X1And X6Same as X2And X5Same as X3And X4The same is true.
In one embodiment of the compounds described herein, L1And L2Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 25 ring carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 24 ring carbon atoms.
In some embodiments of the compounds described herein, L1And L2Each independently selected from the group consisting of a single bond or the following group, but not limited thereto:
wherein the content of the first and second substances,
represents a chemical bond of a compound represented by the formula,
Z1to Z21Independently selected from hydrogen, deuterium, halogen, cyano, carbanoAlkyl with the sub-number of 1-10, haloalkyl with the sub-number of 1-10, cycloalkyl with the sub-number of 3-10, alkoxy with the sub-number of 1-6, aryloxy with the sub-number of 6-18, arylthio with the sub-number of 6-18, aryl with the sub-number of 6-20 and heteroaryl with the sub-number of 3-20;
z is selected from C (R)4R5)，N(R6)，O，S，Si(R4R5)，Se；
R4，R5The same or different, and are respectively and independently selected from substituted or unsubstituted alkyl with 1-10 carbon atoms, substituted or unsubstituted cycloalkyl with 3-10 carbon atoms, substituted or unsubstituted aryl with 6-20 carbon atoms, and substituted or unsubstituted heteroaryl with 3-20 carbon atoms; alternatively, the first and second electrodes may be,
optionally, R4，R5Are linked to each other to form a saturated or unsaturated cyclic group;
x is selected from the following substituted or unsubstituted groups: alkylene having 1 to 10 carbon atoms, cycloalkylene having 3 to 10 carbon atoms, arylene having 6 to 20 carbon atoms, heteroarylene having 3 to 30 carbon atoms;
R6selected from the following substituted or unsubstituted groups: alkyl with 1-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, aryl with 6-20 carbon atoms and heteroaryl with 3-20 carbon atoms;
X1to X10Each independently selected from C or N, and at least one is N;
X11to X15Each independently selected from C or N, and at least one is N;
X16to X23Each independently selected from C or N, and at least one is N;
X24to X27Are each independently selected from C (R)4R5)，N(R6)，O，S，Si(R4R5)，Se；
X28，X29Each independently selected from C or N, and at least one is N;
n1，n3，n4，n6，n7，n8，n9，n15，n17，n19each independently selected from 1,2, 3 or 4;
n2，n14，n16，n20each independently selected from 1,2, 3,4, 5 or 6;
n5，n12，n18each independently selected from 1,2, 3,4, 5,6, 7 or 8;
n13selected from 1,2, 3,4 or 5;
n10，n11each independently selected from 1,2 or 3;
n21selected from 1,2, 3,4, 5,6 or 7.
In some embodiments of the compounds described herein, R4，R5Are independent of each other and are not directly connected; or R4，R5Directly attached, and the atoms commonly attached to form a ring, which may be saturated (e.g., five-membered ring, six-membered ring, adamantane, etc.) or unsaturated. That is, R4，R5The substituents may be independent of each other or may be linked to each other to form a cyclic group, and specific examples of the cyclic group that may be formed include, but are not limited to: cyclopropane, cyclobutane, cyclopentane, cyclohexane, and adamantane.
In some embodiments of the compounds described herein, L1And L2Each independently selected from a single bond or from the group consisting of:
in some embodiments of the compounds described herein, Ar1And Ar2Each independently selected from the following substituted or unsubstituted groups: an aryl group having 6 to 25 ring-forming carbon atoms and a heteroaryl group having 3 to 24 ring-forming carbon atoms.
In some embodiments of the compounds described herein, Ar1And Ar2Each independently selected from the group consisting of, but not limited to:
wherein the content of the first and second substances,
represents a chemical bond of a compound represented by the formula,
T1to T20Each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, alkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, alkoxy having 1 to 6 carbon atoms, aryloxy having 6 to 18 carbon atoms, arylthio having 6 to 18 carbon atoms, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, and arylsilyl having 6 to 24 carbon atoms;
t is selected from C (R)7R8)，N(R9)，O，S，Si(R7R8)，Se；
R7，R8The same or different, each is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms; alternatively, the first and second electrodes may be,
optionally, R7，R8Are linked to each other to form a saturated or unsaturated cyclic group;
w is selected from the following substituted or unsubstituted groups: alkylene having 1 to 10 carbon atoms, cycloalkylene having 3 to 10 carbon atoms, arylene having 6 to 20 carbon atoms, heteroarylene having 3 to 20 carbon atoms;
R9selected from the following substituted or unsubstituted groups: alkyl with 1-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, aryl with 6-20 carbon atoms and heteroaryl with 3-20 carbon atoms;
W1，W2selected from C or N, and at least one is N;
W3to W7Selected from C or N, and at least one is N;
W8to W15Selected from C or N, and at least one is N;
W16，W17are each independently selected from C (R)7R8)，N(R9)，O，S，Si(R7R8)，Se；
e1，e11，e14，e15，e17Each independently selected from 1,2, 3,4 or 5;
e16，e20each independently selected from 1,2 or 3;
e2，e9each independently selected from 1,2, 3,4, 5,6 or 7;
e3，e4，e5each independently selected from 1,2, 3,4, 5,6, 7, 8 or 9;
e6selected from 1,2, 3,4, 5,6, 7 or 8;
e7，e10，e12，e13，e18，e19each independently selected from 1,2, 3 or 4;
e8selected from 1,2, 3,4, 5 or 6.
In some embodiments of the compounds described herein, R7，R8Are independent of each other and are not directly connected; or R4，R5Directly attached, and the atoms commonly attached to form a ring, which may be saturated (e.g., five-membered ring, six-membered ring, adamantane, etc.) or unsaturated. That is, R7，R8The substituents may be independent of each other or may be linked to each other to form a cyclic group, and specific examples of the cyclic group that may be formed include, but are not limited to: cyclopropane, cyclobutane, cyclopentane, cyclohexane, and adamantane.
In some embodiments of the compounds described herein, Ar1And Ar2Each independently selected from the group consisting of, but not limited to:
the compound according to the present application, wherein the compound is selected from any one of the following compounds, but not limited thereto:
another aspect of the present application provides an organic electroluminescent device comprising an anode, a cathode, and a light-emitting layer disposed between the anode and the cathode, wherein a guest material of the light-emitting layer is selected from one or more of the compounds described herein.
In the organic electroluminescent device described herein, the organic electroluminescent device may further include one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a hole blocking layer, an electron injection layer, or an electron transport layer. According to the combination of different organic layers and the compounds contained in each organic layer, the corresponding compounds with different organic layers and high matching degree are selected to improve the photoelectric properties of the compounds.
The present application also provides an organic electroluminescent device comprising an anode, a cathode, an organic layer between the anode and the cathode, wherein the organic layer comprises the compound.
Optionally, the organic layer comprises a light emitting layer comprising the compound.
Optionally, the light emitting layer includes a host material and a guest material, the guest material including the compound.
Optionally, the organic electroluminescent device is a blue light device.
For example, as shown in fig. 2, the organic electroluminescent device includes an anode 100 and a cathode 200 oppositely disposed, and an organic layer 300 disposed between the anode 100 and the cathode 200; the organic layer 300 comprises a compound provided herein.
Alternatively, the compounds provided herein may be used to form at least one organic film layer in the organic layer 300 to improve the lifetime characteristics, efficiency characteristics, and reduce the driving voltage of the organic electroluminescent device; in some embodiments, the mass production stability of the organic electroluminescent device can also be improved.
Optionally, the organic layer 300 includes an electron transport layer 360, the electron transport layer 360 comprising a compound provided herein. The electron transport layer 360 may be composed of the nitrogen-containing compound provided herein, or may be composed of the compound provided herein and other materials.
In one embodiment of the present application, as shown in fig. 1, the organic electroluminescent device may include an anode 100, a hole injection layer 310, a hole transport layer 320, an electron blocking layer 330, an organic light emitting layer 340, a hole blocking layer 350, an electron transport layer 360, an electron injection layer 370, and a cathode 200, which are sequentially stacked. The compound provided by the application can be applied to an electron transport layer 360 and a hole blocking layer 350 of an organic electroluminescent device, and can effectively improve the electron transport property of the organic electroluminescent device. Here, the hole characteristics mean that holes formed in the anode 100 are easily injected into the organic electroluminescent layer 340 and are transported in the organic electroluminescent layer 340 according to conduction characteristics of the HOMO level.
Optionally, the anode 100 comprises an anode material, which is optionally a material with a large work function that facilitates hole injection into the organic 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), polypyrroleAnd polyaniline, but is not limited thereto. Preferably, a transparent electrode including Indium Tin Oxide (ITO) as an anode is included.
Alternatively, the organic light emitting layer 340 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 340 may be composed of a host material and a guest material, and a hole injected into the organic light emitting layer 340 and an electron injected into the organic light emitting layer 340 may be combined in the organic light emitting layer 340 to form an exciton, which transfers energy to the host material, and the host material transfers energy to the guest material, so that the guest material can emit light.
The host material of the organic light emitting layer 340 may be a metal chelate compound, a stilbene-based derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, which are not particularly limited in this application, in one embodiment of the present application, the host material of the organic light emitting layer 340 may be α -ADN.
The guest material of the organic light emitting layer 340 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 compounds of the present application may be used as guest materials for light-emitting layer 340.
The electron transport layer 360 may have a single-layer structure or a multi-layer structure, and may include one or more electron transport materials, and the electron transport materials may be selected from benzimidazole derivatives, oxadiazole derivatives, quinoxaline derivatives, or other electron transport materials, which is not particularly limited in this application. For example, in one embodiment of the present application, the electron transport layer 360 may be composed of DBimiBphen and LiQ.
Optionally, the cathode 200 comprises a cathode material, which is a material with a small work function that facilitates electron injection into the organic layer. Specific examples of the cathode material include: metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or a multi-layer material such as LiF/Al, Liq/Al, LiO2/Al, LiF/Ca, LiF/Al, and BaF2/Ca, but not limited thereto. Preferably, a metal electrode comprising aluminum is included as a cathode.
Optionally, as shown in fig. 2, a hole injection layer 310 may be further disposed between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320. 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. In one embodiment of the present application, the hole injection layer 310 may be composed of m-MTDATA.
Optionally, as shown in fig. 1, an electron injection layer 370 may be further disposed between the cathode 200 and the electron transport layer 360 to enhance the ability to inject electrons into the electron transport layer 360. The electron injection layer 370 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 370 may include LiQ.
The electronic device comprises any one of the electronic elements described in the electronic element embodiment. Since the electronic device has any one of the electronic elements described in the electronic element embodiments, the electronic device has the same beneficial effects, and the details of the electronic device are not repeated herein.
For example, as shown in fig. 3, the present application provides an electronic device 400, wherein the electronic device 400 includes any one of the organic electroluminescent devices described in the organic electroluminescent device embodiments. The electronic device 400 may be a display device, a lighting device, an optical communication device, or other types of electronic devices, and may include, but is not limited to, a computer screen, a mobile phone screen, a television, electronic paper, an emergency light, an optical module, and the like. Since the electronic device 400 has any one of the organic electroluminescent devices described in the organic electroluminescent device embodiments, the same advantages are obtained, and details are not repeated herein.
Hereinafter, the present application will be described in further detail with reference to examples. However, the following examples are merely illustrative of the present application and do not limit the present application.
For the convenience of understanding of the present application, the following raw materials and intermediates correspond to the numbers of the compounds to be prepared, and for example, "raw material 2 a", "raw material 2 b" and "raw material 2 c" respectively refer to raw material Ia, raw material Ib and raw material Ic specifically selected for preparing the compound 2; "starting material 18 a", "starting material 18 b", "intermediate 18 d", "starting material 18 c" and "intermediate 18 e" respectively refer to starting material Ia, starting material Ib, intermediate Id, starting material Ic and intermediate Ie, which are specifically selected for the preparation of compound 18.
Synthesis of Compound intermediate starting Material (example 1 a)
(1) After nitrogen replacement is carried out in a three-mouth reaction bottle provided with a mechanical stirring device, a thermometer and a constant pressure dropping funnel, raw materials 1a-1(200mmol) and 500.0ml of THF are sequentially added, stirring is started, the temperature is reduced to-85 to-90 ℃, 2mol/L n-butyllithium (210mmol) is dropwise added, the temperature in the dropwise adding process is kept at-85 to-90 ℃, heat preservation is carried out for 1h after the dropwise adding is finished, and the solution of the raw materials 2, 5-dichloropyridine-4-aldehyde (200mmol) +140.0ml of THF is dropwise added. After the dropwise addition, the temperature is kept for 0.5h, and the temperature is naturally raised to room temperature for reaction for 3 h. Pouring the reaction solution into 10% ammonium chloride aqueous solution, extracting with 320.0ml toluene, separating, extracting the water phase with 320.0ml toluene for 1 time, combining the organic phase, washing with 260.0ml water for 2 times, separating, adding 12g anhydrous sodium sulfate into the organic phase, drying, filtering, concentrating the organic phase (minus 0.08-0.09 MPa, 55-65 ℃) until the organic phase cannot be discharged, adding 150.0ml petroleum ether, stirring for 0.5h, filtering, leaching the filter cake with petroleum ether to obtain an intermediate 1a-2(104mmol), and obtaining the yield of 52%.
(2) Under the protection of nitrogen in a three-mouth reaction bottle with a mechanical stirrer, a thermometer and a condenser, the intermediate 1a-2(104mmol), p-toluenesulfonic acid (138mmol) and 400.0ml of toluene are sequentially added, the temperature is raised to 100-105 ℃, and the reaction is carried out for 7 hours under the heat preservation condition. Adding 200.0ml of water, separating, extracting the water phase with 200.0ml of toluene, combining organic phases, adding 200.0ml of water, washing for 2 times, separating, adding 10g of anhydrous sodium sulfate into the organic phases, stirring and drying, filtering, concentrating the organic phases to be below (-0.08 to-0.09 MPa, 55-65 ℃) until the organic phases are not discharged, adding 100.0ml of ethanol, stirring and separating out a large amount of solids, filtering, leaching a filter cake with ethanol to obtain 1a-3(72.80mmol), wherein the yield is 70%.
(3) To a three-necked reaction flask equipped with a mechanical stirrer, a thermometer and a condenser under nitrogen protection were added 1a-3(72mmol), cesium carbonate (115mmol), tricyclohexylphosphine tetrafluoroborate (7.2mmol), Pd (OAc)2(1.44mmol) and 350ml of N, N-dimethylacetamide, stirring is started, the temperature is raised to 130-140 ℃, reaction is carried out for 10h, the reaction solution is poured into 200.0ml of water, 300.0ml of dichloroethane is added under stirring, standing and liquid separation are carried out, 300.0ml of dichloroethane is used for 2 times of aqueous phase extraction, organic phases are combined, 200.0ml of water is used for washing the organic phases for 2 times, 10g of anhydrous sodium sulfate is used for drying, filtration is carried out, filtrate passes through (80-120) mesh silica gel column, column passing liquid (50-70 ℃, 0.09-0.08 MPa) is concentrated until the organic phase is not discharged, 100.00ml of N-heptane is added under stirring, filtration is carried out, and the obtained solid crude product is used for 1g of product: recrystallization from 3.2ml of ethyl acetate gave compound 1a (21.60mmol) in 60% overall yield.
The following starting material Ia was synthesized according to the method for the starting material 1a, except that the starting materials 1a-1 and 1a-2 were replaced with the corresponding starting materials Ia-1 and Ia-2, and the starting materials Ia were prepared as shown in Table 1 below.
TABLE 1
Preparation process of raw material Id:
introducing protective gas into a reaction bottle for replacement for 15min, sequentially adding raw materials Id (60mmol), pinacol diboron (72mmol), potassium acetate (120mmol) and 240.0ml of 1.4 dioxane, starting stirring, heating to 45-50 ℃, and rapidly adding PdCl2(dppf) (2.4mmol) and X-phos (2.4mmol), and the reaction is continued to be heated to 80-90 ℃ for 5 h. Reacting under stirringThe solution was slowly poured into water, toluene was added and extracted 2 times, and the organic phases were combined. And washing the organic phase for 3 times, adding anhydrous sodium sulfate into the organic phase, passing through a silica gel column, concentrating the column passing liquid until no liquid drops flow out, adding petroleum ether under stirring, and filtering to obtain 51mmol of an intermediate Id.
Example 1 (Compound 1)
Under the protection of nitrogen, sequentially adding raw materials 1a (20mmol, 1.0eq), 1b (18mmol, 0.9eq), toluene (45mL), ethanol (5mL), water (5mL) and potassium carbonate (50mmol, 2.5eq) into a reaction bottle, starting heating and stirring, adding tetrakis (triphenylphosphine) palladium (0.1mmol, 0.005eq) into the reaction system when the temperature of the reaction system rises to 50 ℃, continuously heating to a reflux state, and stirring overnight. Stopping the reaction when the liquid phase monitoring reaction is complete, adding water into the reaction system when the reaction system is cooled to normal temperature, extracting twice with toluene, combining organic phases, drying with anhydrous sodium sulfate, and separating and purifying by a column to obtain 1-14.59g of an intermediate, wherein the yield is as follows: 82.60 percent.
Under the protection of nitrogen, tetrahydrofuran (45mL) is sequentially added into a reaction bottle, stirring is started, then intermediate 1-1(16mmol, 1.0eq) is added into the reaction system, when solid materials are completely dissolved, the temperature of the reaction system is reduced to-78 ℃ by using a liquid nitrogen ethanol bath, n-butyl lithium (20.8mmol, 1.3eq) is slowly dropped into the reaction system, the temperature of the reaction system is kept between 80 ℃ below zero and 60 ℃ below zero for reaction for 1.5 hours after dropping, then raw material 1c (14.4mmol, 0.9eq) is added into the reaction system in batches at the temperature, and after feeding, the temperature is slowly returned, and stirring is carried out overnight. Saturated ammonium chloride solution was added to the reaction system, stirred for 5 minutes, then extracted twice with dichloroethane, the organic phases were collected and combined, dried over anhydrous sodium sulfate, concentrated to dryness, and then purified by boiling with n-heptane to give 1 to 25.51 g of intermediate, yield: 75.06 percent.
Under the protection of nitrogen, sequentially adding toluene (55mL) into a reaction bottle, starting stirring, then adding 1-2(12mmol, 1.0eq) of an intermediate into a reaction system, adding p-toluenesulfonic acid (3.6mmol, 0.3eq) into the reaction system after solid materials are completely dissolved, starting heating, heating the reaction system to a reflux state, observing through a water separator until anhydrous drops are separated out, additionally refluxing for 1 hour, and stopping the reaction when the liquid phase monitors that the reaction is complete. When the temperature of the reaction system is reduced to room temperature, filtering the reaction solution through diatomite to remove insoluble residues, concentrating and drying the filtrate, and directly carrying out the next reaction without further purification to obtain 1-35.03 g of an intermediate, wherein the yield is as follows: 95 percent.
Under the protection of nitrogen, dichloromethane (50mL) is sequentially added into a reaction bottle, stirring is started, then 1-3(11mmol, 1.0eq) of an intermediate is added into the reaction system, when solid materials are completely dissolved, the temperature of the reaction system is reduced to-5 ℃ by using an ice salt bath, boron trifluoride diethyl etherate complex (11mmol, 1.0eq) is slowly dropped into the reaction system, then 2, 3-dichloro-5, 6-dicyano-1, 4-benzoquinone (16.5mmol, 1.5eq) is added into the reaction system, the process of 2, 3-dichloro-5, 6-dicyano-1, 4-benzoquinone is added into the reaction system, the temperature of the reaction system is between-10 ℃ and 0 ℃ after the feeding is finished, the reaction system is kept at the temperature between-10 ℃ and 0 ℃ for 5 hours, and the reaction is stopped when the liquid phase monitoring is complete. The reaction solution was then filtered through celite to remove insoluble residues, rinsed with dichloromethane, the filtrate was concentrated to dryness, and then recrystallized from toluene to give 1-43.17 g of intermediate, yield: 65.75 percent.
Under the protection of nitrogen, sequentially adding 1-4(7mmol, 1.0eq), 1-5(6.3mmol, 0.9eq), 1, 4-dioxane (30mL), 6mL of water and 17.5mmol, 2.5eq to a reaction bottle, starting heating and stirring, adding 0.07mmol, 0.01eq of tetrakis (triphenylphosphine) palladium to the reaction system when the temperature of the reaction system rises to 50 ℃, continuously heating to a reflux state, and stirring overnight. Stopping the reaction when the liquid phase monitoring reaction is completed, adding water into the reaction system when the reaction system is cooled to normal temperature, extracting twice with dichloroethane, combining organic phases, drying with anhydrous sodium sulfate, removing part of pigments and insoluble impurities through column separation and purification, concentrating and drying eluent, and recrystallizing with toluene to obtain 3.77g of a compound 1 with yield: 91.70 percent. Mass spectrometry data: m/z 587.2[ M + H [ ]]+。
Example 2 (Compound 43)
Under the protection of nitrogen, raw material 43a (20mmol, 1.0eq), raw material 43b (18mmol, 0.9eq), toluene (45mL), ethanol (5mL), water (5mL) and potassium carbonate (50mmol, 2.5eq) are sequentially added into a reaction bottle, heating and stirring are started, when the temperature of a reaction system rises to 50 ℃, tetrakis (triphenylphosphine) palladium (0.1mmol, 0.005eq) is added into the reaction system, the temperature is continuously raised to a reflux state, and stirring is carried out overnight. Stopping the reaction when the liquid phase monitoring reaction is complete, adding water into the reaction system when the reaction system is cooled to normal temperature, extracting twice with toluene, combining organic phases, drying with anhydrous sodium sulfate, and separating and purifying by a column to obtain 32-17.56 g of an intermediate, wherein the yield is as follows: 80 percent.
Under the protection of nitrogen, tetrahydrofuran (45mL) is sequentially added into a reaction bottle, stirring is started, then the intermediate 43-1(16mmol, 1.0eq) is added into the reaction system, when solid materials are completely dissolved, the temperature of the reaction system is reduced to-78 ℃ by using a liquid nitrogen ethanol bath, n-butyl lithium (20.8mmol, 1.3eq) is slowly dropped into the reaction system, the temperature of the reaction system is kept between 80 ℃ below zero and 60 ℃ below zero for reaction for 1.5 hours after dropping is finished, then the raw material 43c (14.4mmol, 0.9eq) is added into the reaction system in batches at the temperature, and after the feeding is finished, the temperature is slowly returned, and stirring is carried out overnight. Saturated ammonium chloride solution was added to the reaction system, stirred for 5 minutes, then extracted twice with dichloroethane, the organic phases were collected and combined, dried over anhydrous sodium sulfate, concentrated to dryness, and then purified by boiling with n-heptane to give intermediate 43-26.44g, yield: 72 percent.
Under the protection of nitrogen, sequentially adding toluene (55mL) into a reaction bottle, starting stirring, then adding the intermediate 43-2(11mmol, 1.0eq) into the reaction system, adding p-toluenesulfonic acid (3.3mmol, 0.3eq) into the reaction system after solid materials are completely dissolved, starting heating, heating the reaction system to a reflux state, observing through a water separator until anhydrous drops are separated out, additionally refluxing for 1 hour, and stopping the reaction when the liquid phase monitors that the reaction is complete. When the temperature of the reaction system is reduced to room temperature, filtering the reaction solution through diatomite to remove insoluble residues, concentrating and drying the filtrate, and directly carrying out the next reaction without further purification to obtain 43-35.52 g of an intermediate, wherein the yield is as follows: 95 percent.
Under the protection of nitrogen, dichloromethane (50mL) is sequentially added into a reaction bottle, stirring is started, then the intermediate 43-3(11mmol, 1.0eq) is added into the reaction system, when solid materials are completely dissolved, the temperature of the reaction system is reduced to-5 ℃ by using an ice salt bath, boron trifluoride diethyl etherate complex (11mmol, 1.0eq) is slowly dropped into the reaction system, then 2, 3-dichloro-5, 6-dicyano-1, 4-benzoquinone (16.5mmol, 1.5eq) is added into the reaction system, the process of 2, 3-dichloro-5, 6-dicyano-1, 4-benzoquinone is added into the reaction system, the temperature of the reaction system is between-10 ℃ and 0 ℃ after the feeding is finished, the reaction system is kept at the temperature between-10 ℃ and 0 ℃ for 5 hours, and the reaction is stopped when the liquid phase monitoring is completely carried out. The reaction was then filtered through celite to remove insoluble residues, rinsed with dichloromethane, the filtrate concentrated to dryness, and then recrystallized from toluene to afford intermediate 43-43.85 g, yield: 65 percent.
Under the protection of nitrogen, adding the intermediate 43-4(7mmol, 1.0eq), the intermediate 43-5(6.3mmol, 0.9eq), 1, 4-dioxane (30mL), water (6mL), potassium carbonate (17.5mmol, 2.5eq) into a reaction bottle in sequence, starting heating and stirring, adding tetrakis (triphenylphosphine) palladium (0.07mmol, 0.01eq) into the reaction system when the temperature of the reaction system rises to 50 ℃, continuing to heat to a reflux state, and stirring overnight. Stopping the reaction when the liquid phase monitoring reaction is completed, adding water into the reaction system when the reaction system is cooled to normal temperature, extracting twice with dichloroethane, combining organic phases, drying with anhydrous sodium sulfate, removing part of pigments and insoluble impurities through column separation and purification, concentrating and drying eluent, and recrystallizing with toluene to obtain 3.62g of a compound 43 with yield: 89 percent. Mass spectrometry data: 581.2[ M + H ] M/z]+。
Example 3 (Compound 85)
Under the protection of nitrogen, raw materials 85a (20mmol, 1.0eq), 85b (18mmol, 0.9eq), toluene (45mL), ethanol (5mL), water (5mL) and potassium carbonate (50mmol, 2.5eq) are sequentially added into a reaction bottle, heating and stirring are started, when the temperature of a reaction system rises to 50 ℃, tetrakis (triphenylphosphine) palladium (0.1mmol, 0.005eq) is added into the reaction system, the temperature is continuously increased to a reflux state, and stirring is carried out overnight. Stopping the reaction when the liquid phase monitoring reaction is complete, adding water into the reaction system when the reaction system is cooled to normal temperature, extracting twice with toluene, combining organic phases, drying with anhydrous sodium sulfate, and performing column separation and purification to obtain 85-14.72 g of an intermediate, wherein the yield is as follows: 85 percent.
Under the protection of nitrogen, tetrahydrofuran (47mL) is sequentially added into a reaction bottle, stirring is started, then, the intermediate 85-1(17mmol, 1.0eq) is added into a reaction system, when solid materials are completely dissolved, the reaction system is cooled to-78 ℃ by a liquid nitrogen ethanol bath, n-butyl lithium (22.1mmol, 1.3eq) is slowly dropped into the reaction system, the temperature of the reaction system is kept between 80 ℃ below zero and 60 ℃ below zero for reaction for 1.5 hours after dropping, then, the raw material 85c (15.3mmol, 0.9eq) is added into the reaction system in batches at the temperature, and after feeding, the temperature is slowly returned, and stirring is carried out overnight. Saturated ammonium chloride solution was added to the reaction system, stirred for 5 minutes, then extracted twice with dichloroethane, the organic phases were collected and combined, dried over anhydrous sodium sulfate, concentrated to dryness, and then purified by boiling with n-heptane to give intermediate 85-26.08g, yield: 78 percent.
Under the protection of nitrogen, sequentially adding toluene (60mL) into a reaction bottle, starting stirring, then adding the intermediate 85-2(13mmol, 1.0eq) into the reaction system, adding p-toluenesulfonic acid (3.93mmol, 0.3eq) into the reaction system after solid materials are completely dissolved, starting heating, heating the reaction system to a reflux state, observing through a water separator until anhydrous drops are separated out, additionally refluxing for 1 hour, and stopping the reaction when the liquid phase monitors that the reaction is complete. When the temperature of the reaction system is reduced to room temperature, filtering the reaction solution through diatomite to remove insoluble residues, concentrating and drying the filtrate, and directly carrying out the next reaction without further purification to obtain 85-35.45 g of an intermediate, wherein the yield is as follows: 95 percent.
Under the protection of nitrogen, dichloromethane (55mL) is sequentially added into a reaction bottle, stirring is started, then the intermediate 43-3(12mmol, 1.0eq) is added into the reaction system, when solid materials are completely dissolved, the temperature of the reaction system is reduced to-5 ℃ by using an ice salt bath, boron trifluoride diethyl etherate complex (12mmol, 1.0eq) is slowly dropped into the reaction system, then 2, 3-dichloro-5, 6-dicyano-1, 4-benzoquinone (18mmol, 1.5eq) is added into the reaction system, the process of 2, 3-dichloro-5, 6-dicyano-1, 4-benzoquinone is added, the temperature of the reaction system is between-10 ℃ and 0 ℃ after feeding is finished, the reaction system is kept at-10 ℃ and 0 ℃ for 5 hours, and the reaction is stopped when the liquid phase monitoring is completed. The reaction was then filtered through celite to remove insoluble residues, rinsed with dichloromethane, the filtrate concentrated to dryness, and then recrystallized from toluene to afford intermediates 85-43.42 g, yields: 65 percent.
Under the protection of nitrogen, adding the intermediate 85-4(7.5mmol, 1.0eq), the intermediate 85-5(6.75mmol, 0.9eq), 1, 4-dioxane (30mL), water (6mL), potassium carbonate (18.75mmol, 2.5eq) into a reaction bottle in sequence, starting heating and stirring, adding tetrakis (triphenylphosphine) palladium (0.075mmol, 0.01eq) into the reaction system when the temperature of the reaction system rises to 50 ℃, continuing to rise to the reflux state, and stirring overnight. Stopping the reaction when the liquid phase monitoring reaction is completed, adding water into the reaction system when the reaction system is cooled to normal temperature, extracting twice with dichloroethane, combining organic phases, drying with anhydrous sodium sulfate, removing part of pigments and insoluble impurities through column separation and purification, concentrating and drying eluent, and recrystallizing with toluene to obtain 3.89g of compound 853 with yield: 82 percent. Mass spectrometry data: 633.2[ M + H ] M/z]+。
Examples 4 to 11
The compounds of examples 4 to 11 were synthesized according to the methods of examples 1 to 3, except that the raw materials 1a, 1b, 1c and 1d in example 1 were replaced with the corresponding raw materials, and the raw materials used, the compounds prepared accordingly, and the mass spectrum data are specifically shown in table 2.
TABLE 2
Device part
The following application examples 1 to 11 are used to illustrate the application of the compound of the present application to a light emitting layer in an organic electroluminescent device.
Application example 1
A method of manufacturing an organic light emitting device, comprising the steps of:
(1) firstly, distilled water and methanol are sequentially used for ultrasonic cleaning
Drying a glass bottom plate of an Indium Tin Oxide (ITO) electrode;
(2) cleaning the anode base plate for 5 minutes by using oxygen plasma, and then loading the cleaned anode base plate into vacuum deposition equipment;
(3) the compound 2-TNATA (CAS: 185690-41-9) was vacuum deposited onto an ITO electrode
A hole injection layer 310 of a thickness and vacuum depositing NPB (N, N '-diphenyl-N, N' -di (1-naphthyl) -1, 1 '-biphenyl-4, 4' -diamine) on the hole injection layer
A hole transport layer 320 with a thickness, and TCTA (structure shown in formula A) is deposited on the hole transport layer to form
Electron blocking layer 330 with thickness then co-depositing host luminescent material α -ADN (structure shown in formula B) and compound 1 as guest on the electron blocking layer according to film thickness ratio of 100:3 to form
Thickness of hairAn optical layer 340;
(4) will be provided with
The hole blocking layer 350 is formed on the light-emitting layer by vacuum deposition of the hole blocking layer TPBi;
(5) mixing DBimiBphen (structure shown as formula C) and LiQ (structure shown as formula D) at a weight ratio of 1:1, and vacuum-depositing on the hole blocking layer to form
Electron transport layer 360 of thickness. Then, LiQ (8-hydroxyquinoline-lithium) was evaporated on the electron transport layer to form
An electron injection layer 370 with a thickness of 1: 9, and magnesium (Mg) and silver (Ag) are mixed at a vapor deposition rate, and vacuum-deposited on the electron injection layer to form
The cathode with the thickness of
CP-1 (structural formula can be seen below), and a capping layer (CPL) was formed, thereby completing the fabrication of an organic light emitting device, which was designated as a 1.
Comparative examples 1 to 2
In comparative examples 1 and 2, organic electroluminescent devices, which were respectively denoted as D1 and D2, were fabricated in the same manner as in example 1, except that BD-6MDPA and compound a were used as guest materials for the light-emitting layer, respectively, instead of compound 1. Wherein, the structural formulas of the BD-6MDPA and the compound A are respectively shown as follows:
application example 2 to application example 11
Organic electroluminescent devices a2 to a11 were produced in the same manner as in application example 1, except that in application examples 2 to 11, compounds shown in table 2 were used as guest materials instead of compound 1, respectively.
Fabrication of organic electroluminescent devices
The organic electroluminescent devices A1 to A11 and D1 and D2 prepared as above were each heated at 15mA/cm2The life of the T95 device was tested under the condition that the data voltage, efficiency and color coordinate are 10mA/cm at constant current density2The following tests were carried out and the results are shown in Table 3.
Table 3 performance test results of organic electroluminescent device
From the above results, it is clear that the compound of the present application as a light-emitting guest material is compared with comparative examples 1 and 2 using known light-emitting guest materials:
the driving voltages of the organic electroluminescent devices A1 to A11 prepared in application examples 1 to 11 are between 3.8 and 3.9V, and are at least 0.2V lower than the driving voltage of the organic electroluminescent device of the comparative example.
The luminous efficiency of the organic electroluminescent devices A1-A11 is 6.1-6.8 Cd/A, and is improved by 20-35% compared with the luminous efficiency (average value of 5.05) of the comparative organic electroluminescent devices. The external quantum efficiency of the organic electroluminescent devices A1-A11 is 10.6-12.9%, which is improved by 33-62% compared with the external quantum efficiency (average value of 7.95) of a comparative example. The T95 service life of the organic electroluminescent devices A1-A10 is 178-258 h, which is 11-61% longer than the service life (average value 160) of the comparative T95.
It can be seen that the organic electroluminescent devices a1 to a11 prepared in application examples 1 to 11 had lower driving voltage, higher luminous efficiency, higher external quantum efficiency, and brightness, compared to the devices of the comparative examples.
The organic electroluminescent device adopting the compound disclosed by the application has excellent performances in the aspects of chromaticity, service life and the like.
Compared with BD-6MDPA and the compound A, the condensed ring compound parent nucleus, aryl and heteroaryl substituent groups adopted by the compound are easy to form a large conjugated system, a plurality of nitrogen atom centers exist at the same time, the density of electron clouds in molecules is increased, the HOMO energy level can be further adjusted to a proper level, the electron mobility and the transition rate are further improved, and the organic electroluminescent device has high device efficiency. The performance of the organic electroluminescent device can be remarkably improved when the organic electroluminescent device is used for a light emitting layer of the organic electroluminescent device.
In the present application, the organic electroluminescent device may be used in an organic light-emitting electronic device, wherein the electronic device may be a display screen of a mobile phone, a computer display screen, a television display screen, a display screen of a smart watch, a display screen of an organic electroluminescent device of a smart car, a display screen of a VR or AR helmet, a display screen of various smart devices, and the like. Fig. 3 is a schematic view of an electronic device according to an embodiment of the present application. In fig. 3, 400 denotes a display panel of a cellular phone including an organic electroluminescent device.
Although the present application has been described with reference to preferred embodiments, it is not intended to limit the scope of the claims, and many possible variations and modifications may be made by one skilled in the art without departing from the spirit of the application.
Claims (13)
1. A compound having a structure represented by chemical formula 1:
wherein, X1、X2、X3、X4、X5And X6Each independently selected from a C atom or a N atom, and X1、X2、X3And only one is an N atom, X4、X5And X6And only one of them is an N atom;
L1and L2Each independently selected from a single bond, a substituted or unsubstituted alkylene group having 1 to 20 carbon atoms, a substituted or unsubstituted cycloalkylene group having 3 to 20 carbon atoms, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms;
Ar1and Ar2Each independently selected from the following substituted or unsubstituted groups: alkyl group having 1 to 20 carbon atoms, cycloalkyl group having 3 to 20 carbon atoms, aryl group having 6 to 30 carbon atoms, heteroaryl group having 3 to 30 carbon atoms, Si (R)1R2R3)；
R1，R2，R3Each independently selected from the following substituted or unsubstituted groups: an alkyl group having 1 to 20 carbon atoms and an aryl group having 6 to 30 carbon atoms.
2. The compound of claim 1, wherein L is1And L2、Ar1And Ar2The substituents are the same or different and are each independently selected from deuterium, halogen, cyano, alkyl having 1 to 12 carbon atoms, alkoxy having 1 to 12 carbon atoms, alkylthio having 1 to 12 carbon atoms, haloalkyl having 1 to 12 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, cycloalkyl having 3 to 12 carbon atoms, aryloxy having 6 to 18 carbon atoms, arylthio having 6 to 18 carbon atoms, aryl having 6 to 18 carbon atoms, heteroaryl having 3 to 18 carbon atoms and arylsilyl having 6 to 24 carbon atoms.
3. The compound of claim 1, wherein L is1And L2Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 25 ring carbon atoms, and a substituted or unsubstituted heteroarylene group having 3 to 24 ring carbon atoms.
4. The compound of claim 1, wherein L is1And L2Each independently selected from a single bond or from the group consisting of:
wherein the content of the first and second substances,
represents a chemical bond of a compound represented by the formula,
Z1to Z21Independently selected from hydrogen, deuterium, halogen, cyano, alkyl having 1 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, alkoxy having 1 to 6 carbon atoms, aryloxy having 6 to 18 carbon atoms, arylthio having 6 to 18 carbon atoms, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms;
z is selected from C (R)4R5)，N(R6)，O，S，Si(R4R5)，Se；
R4，R5The same or different, each is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms; alternatively, the first and second electrodes may be,
optionally, R4，R5Are linked to each other to form a saturated or unsaturated cyclic group;
x is selected from the following substituted or unsubstituted groups: alkylene having 1 to 10 carbon atoms, cycloalkylene having 3 to 10 carbon atoms, arylene having 6 to 20 carbon atoms, heteroarylene having 3 to 30 carbon atoms;
R6selected from the following substituted or unsubstituted groups: alkyl with 1-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, aryl with 6-20 carbon atoms and heteroaryl with 3-20 carbon atoms;
X1to X10Each independently selected from C or N, and at least one is N;
X11to X15Each independently selected from C or N, and at least one is N;
X16to X23Each independently selected from C or N, and at least one is N;
X24to X27Are each independently selected from C (R)4R5)，N(R6)，O，S，Si(R4R5)，Se；
X28，X29Each independently selected from C or N, and at least one is N;
n1，n3，n4，n6，n7，n8，n9，n15，n17，n19each independently selected from 1,2, 3 or 4;
n2，n14，n16，n20each independently selected from 1,2, 3,4, 5 or 6;
n5，n12，n18each independently selected from 1,2, 3,4, 5,6, 7 or 8;
n13selected from 1,2, 3,4 or 5;
n10，n11each independently selected from 1,2 or 3;
n21selected from 1,2, 3,4, 5,6 or 7.
5. The compound of claim 1, wherein L is1And L2Each independently selected from a single bond or from the group consisting of:
6. the compound of claim 1, wherein Ar is Ar1And Ar2Each independently selected from the following substituted or unsubstituted groups: an aryl group having 6 to 25 ring-forming carbon atoms and a heteroaryl group having 3 to 24 ring-forming carbon atoms.
7. The compound of claim 1, wherein Ar is Ar1And Ar2Each independently selected from the group consisting of:
wherein the content of the first and second substances,
represents a chemical bond of a compound represented by the formula,
T1to T20Each independently selected from the group consisting of hydrogen, deuterium, halogen, cyano, alkyl having 1 to 10 carbon atoms, cycloalkyl having 3 to 10 carbon atoms, haloalkyl having 1 to 10 carbon atoms, alkoxy having 1 to 6 carbon atoms, aryloxy having 6 to 18 carbon atoms, arylthio having 6 to 18 carbon atoms, aryl having 6 to 20 carbon atoms, heteroaryl having 3 to 20 carbon atoms, trialkylsilyl having 3 to 12 carbon atoms, and arylsilyl having 6 to 24 carbon atoms;
t is selected from C (R)7R8)，N(R9)，O，S，Si(R7R8)，Se；
R7，R8The same or different, each is independently selected from hydrogen, deuterium, substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, substituted or unsubstituted aryl group having 6 to 20 carbon atoms, and substituted or unsubstituted heteroaryl group having 3 to 20 carbon atoms; alternatively, the first and second electrodes may be,
optionally, R7，R8Are linked to each other to form a saturated or unsaturated cyclic group;
w is selected from the following substituted or unsubstituted groups: alkylene having 1 to 10 carbon atoms, cycloalkylene having 3 to 10 carbon atoms, arylene having 6 to 20 carbon atoms, heteroarylene having 3 to 20 carbon atoms;
R9selected from the following substituted or unsubstituted groups: alkyl with 1-10 carbon atoms, cycloalkyl with 3-10 carbon atoms, aryl with 6-20 carbon atoms and heteroaryl with 3-20 carbon atoms;
W1，W2each independently selected from C or N, and at least one is N;
W3to W7Each independently selected from C or N, and at least one is N;
W8to W15Each independently selected from C or N, and at least one is N;
W16，W17are each independently selected from C (R)7R8)，N(R9)，O，S，Si(R7R8)，Se；
e1，e11，e14，e15，e17Each independently selected from 1,2, 3,4 or 5;
e16，e20each independently selected from 1,2 or 3;
e2，e9each independently selected from 1,2, 3,4, 5,6 or 7;
e3，e4，e5each independently selected from 1,2, 3,4, 5,6, 7, 8 or 9;
e6selected from 1,2, 3,4, 5,6, 7 or 8;
e7，e10，e12，e13，e18，e19each independently selected from 1,2, 3 or 4;
e8selected from 1,2, 3,4, 5 or 6.
8. The compound of claim 1, wherein Ar is Ar1And Ar2Each independently selected from the group consisting of:
9. the compound of claim 1, wherein the compound is selected from any one of the following compounds:
10. an organic electroluminescent device comprising an anode, a cathode and an organic layer disposed between the cathode and the anode;
the organic layer comprises a compound of any one of claims 1-9.
11. The organic electroluminescent device according to claim 10, wherein the organic layer comprises a light-emitting layer comprising a host material and a guest material comprising the compound according to any one of claims 1 to 9.
12. The organic electroluminescent device according to claim 10 or 11, wherein the organic electroluminescent device is a blue light device.
13. An electronic device comprising the organic electroluminescent element as claimed in any one of claims 10 to 12.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911369556.7A CN111072659A (en) | 2019-12-26 | 2019-12-26 | Compound, organic electroluminescent device, and electronic device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911369556.7A CN111072659A (en) | 2019-12-26 | 2019-12-26 | Compound, organic electroluminescent device, and electronic device |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN111072659A true CN111072659A (en) | 2020-04-28 |
Family
ID=70318504
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911369556.7A Withdrawn CN111072659A (en) | 2019-12-26 | 2019-12-26 | Compound, organic electroluminescent device, and electronic device |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111072659A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111018722A (en) * | 2019-12-30 | 2020-04-17 | 陕西莱特光电材料股份有限公司 | Compound, organic electroluminescent device, and electronic device |
| CN114621208A (en) * | 2022-03-07 | 2022-06-14 | 京东方科技集团股份有限公司 | Light extraction material, organic electroluminescent device, and display device |
| CN114874176A (en) * | 2022-02-11 | 2022-08-09 | 京东方科技集团股份有限公司 | Heterocyclic compound, application and organic electroluminescent device |
| CN115322189A (en) * | 2021-09-28 | 2022-11-11 | 四川阿格瑞新材料有限公司 | Spiro compound and application thereof |
-
2019
- 2019-12-26 CN CN201911369556.7A patent/CN111072659A/en not_active Withdrawn
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111018722A (en) * | 2019-12-30 | 2020-04-17 | 陕西莱特光电材料股份有限公司 | Compound, organic electroluminescent device, and electronic device |
| CN115322189A (en) * | 2021-09-28 | 2022-11-11 | 四川阿格瑞新材料有限公司 | Spiro compound and application thereof |
| CN115322189B (en) * | 2021-09-28 | 2023-11-28 | 四川阿格瑞新材料有限公司 | Spiro compound and application thereof |
| CN114874176A (en) * | 2022-02-11 | 2022-08-09 | 京东方科技集团股份有限公司 | Heterocyclic compound, application and organic electroluminescent device |
| CN114621208A (en) * | 2022-03-07 | 2022-06-14 | 京东方科技集团股份有限公司 | Light extraction material, organic electroluminescent device, and display device |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111072659A (en) | Compound, organic electroluminescent device, and electronic device | |
| CN111454197A (en) | Nitrogen-containing compound, organic electroluminescent device, and electronic device | |
| CN112500410B (en) | Spiro nitrogen-containing organic luminescent compound, and preparation method and application thereof | |
| CN113285038B (en) | Organic electroluminescent device and electronic device | |
| WO2022170831A1 (en) | Organic electroluminescent material, electronic element and electronic apparatus | |
| WO2022127518A1 (en) | Nitrogen-containing organic compound and electronic component and electronic apparatus using same | |
| CN113121588B (en) | Organic compound, electronic element containing organic compound and electronic device | |
| CN114075215B (en) | Organic compound, organic electroluminescent device comprising same and electronic device | |
| CN111018854B (en) | Compound, organic electroluminescent device, and electronic device | |
| CN111004237A (en) | Compound, organic electroluminescent device, and electronic device | |
| CN111018722A (en) | Compound, organic electroluminescent device, and electronic device | |
| CN114805179A (en) | Nitrogen-containing compound, organic electroluminescent device, and electronic device | |
| CN114315836B (en) | Organic compound, organic electroluminescent device comprising same and electronic device | |
| CN112457278B (en) | Organic electroluminescent compound and preparation method and application thereof | |
| CN113372321B (en) | Organic compound, and electronic device and apparatus comprising the same | |
| CN113105462A (en) | Organic compound, and electronic element and electronic device using same | |
| CN113421980B (en) | Organic electroluminescent device and electronic apparatus including the same | |
| CN114149443B (en) | Nitrogen-containing compound, electronic component and electronic device | |
| CN113380954B (en) | Organic electroluminescent device and electronic apparatus | |
| CN111039962B (en) | Nitrogen-containing compound, application thereof and organic electroluminescent device using nitrogen-containing compound | |
| CN110938073A (en) | Compound, organic electroluminescent device, and electronic device | |
| CN115394942A (en) | Organic electroluminescent device and electronic device | |
| CN115968591A (en) | Organic light emitting device comprising organic compound | |
| CN113972332B (en) | Organic electroluminescent device and electronic device including the same | |
| CN114335399B (en) | Organic electroluminescent device and electronic device including the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WW01 | Invention patent application withdrawn after publication | ||
| WW01 | Invention patent application withdrawn after publication |
Application publication date: 20200428 |