CN114516859A - Compound and application thereof - Google Patents
Compound and application thereof Download PDFInfo
- Publication number
- CN114516859A CN114516859A CN202011291799.6A CN202011291799A CN114516859A CN 114516859 A CN114516859 A CN 114516859A CN 202011291799 A CN202011291799 A CN 202011291799A CN 114516859 A CN114516859 A CN 114516859A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 76
- 239000000463 material Substances 0.000 claims abstract description 46
- -1 nitro, hydroxyl Chemical group 0.000 claims description 130
- 239000010410 layer Substances 0.000 claims description 54
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 30
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 24
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 20
- 125000001769 aryl amino group Chemical group 0.000 claims description 15
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 235000010290 biphenyl Nutrition 0.000 claims description 12
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 12
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000001624 naphthyl group Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 239000002346 layers by function Substances 0.000 claims description 10
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 9
- 239000004305 biphenyl Substances 0.000 claims description 9
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 9
- 125000002541 furyl group Chemical group 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 8
- 125000005549 heteroarylene group Chemical group 0.000 claims description 8
- 125000005990 isobenzothienyl group Chemical group 0.000 claims description 8
- 125000004957 naphthylene group Chemical group 0.000 claims description 8
- 125000005561 phenanthryl group Chemical group 0.000 claims description 8
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 8
- 125000006836 terphenylene group Chemical group 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- 125000005730 thiophenylene group Chemical group 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 6
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 6
- 125000001725 pyrenyl group Chemical group 0.000 claims description 6
- 239000002019 doping agent Substances 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 claims description 5
- 239000010409 thin film Substances 0.000 claims description 5
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 claims description 4
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 3
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 2
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000005551 pyridylene group Chemical group 0.000 claims description 2
- 125000005576 pyrimidinylene group Chemical group 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000005558 triazinylene group Chemical group 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 1
- 230000005525 hole transport Effects 0.000 abstract description 15
- 125000005266 diarylamine group Chemical group 0.000 abstract description 5
- 238000006243 chemical reaction Methods 0.000 description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 21
- 238000003786 synthesis reaction Methods 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- 238000001819 mass spectrum Methods 0.000 description 9
- 238000012544 monitoring process Methods 0.000 description 9
- 238000004809 thin layer chromatography Methods 0.000 description 9
- 238000004440 column chromatography Methods 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- 239000008204 material by function Substances 0.000 description 6
- 239000002356 single layer Substances 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 229910000024 caesium carbonate Inorganic materials 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- LTBWKAYPXIIVPC-UHFFFAOYSA-N 3-bromo-9h-carbazole Chemical compound C1=CC=C2C3=CC(Br)=CC=C3NC2=C1 LTBWKAYPXIIVPC-UHFFFAOYSA-N 0.000 description 4
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- SFKMVPQJJGJCMI-UHFFFAOYSA-N 2-chloro-4-phenylquinazoline Chemical compound C=12C=CC=CC2=NC(Cl)=NC=1C1=CC=CC=C1 SFKMVPQJJGJCMI-UHFFFAOYSA-N 0.000 description 2
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NSGDYZCDUPSTQT-UHFFFAOYSA-N N-[5-bromo-1-[(4-fluorophenyl)methyl]-4-methyl-2-oxopyridin-3-yl]cycloheptanecarboxamide Chemical compound Cc1c(Br)cn(Cc2ccc(F)cc2)c(=O)c1NC(=O)C1CCCCCC1 NSGDYZCDUPSTQT-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229910052769 Ytterbium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 238000007350 electrophilic reaction Methods 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 239000010408 film Substances 0.000 description 2
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- 239000011777 magnesium Substances 0.000 description 2
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 2
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000002207 thermal evaporation Methods 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- GJZLFBBCBVKUKW-UHFFFAOYSA-N 2-(2-fluorophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound FC1=C(C=CC=C1)C1=NC(=NC(=N1)C1=CC=CC=C1)C1=CC=CC=C1 GJZLFBBCBVKUKW-UHFFFAOYSA-N 0.000 description 1
- KPGPIQKEKAEAHM-UHFFFAOYSA-N 2-chloro-3-phenylquinoxaline Chemical compound ClC1=NC2=CC=CC=C2N=C1C1=CC=CC=C1 KPGPIQKEKAEAHM-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- MHHGZIWKFOLVJP-UHFFFAOYSA-N 5-bromo-1-n,1-n,3-n,3-n-tetraphenylbenzene-1,3-diamine Chemical group C=1C(Br)=CC(N(C=2C=CC=CC=2)C=2C=CC=CC=2)=CC=1N(C=1C=CC=CC=1)C1=CC=CC=C1 MHHGZIWKFOLVJP-UHFFFAOYSA-N 0.000 description 1
- BGEVROQFKHXUQA-UHFFFAOYSA-N 71012-25-4 Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=C1C1=CC=CC=C1N2 BGEVROQFKHXUQA-UHFFFAOYSA-N 0.000 description 1
- OXYFZHUGVBINOL-UHFFFAOYSA-N 8-bromo-5h-pyrido[3,2-b]indole Chemical compound C1=CN=C2C3=CC(Br)=CC=C3NC2=C1 OXYFZHUGVBINOL-UHFFFAOYSA-N 0.000 description 1
- QQZKFCZEMHCHMK-UHFFFAOYSA-N 8-bromo-5h-pyrido[4,3-b]indole Chemical group C1=NC=C2C3=CC(Br)=CC=C3NC2=C1 QQZKFCZEMHCHMK-UHFFFAOYSA-N 0.000 description 1
- ZHQNDEHZACHHTA-UHFFFAOYSA-N 9,9-dimethylfluorene Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 ZHQNDEHZACHHTA-UHFFFAOYSA-N 0.000 description 1
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical compound C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 1
- JTPHKHUWLNQSSU-UHFFFAOYSA-N C1=CC=CC=2C=CC=3C=4C=CC=CC4NC3C21.C2(=CC=CC1=CC=CC=C21)N2C1=CC=CC=C1C=1C=CC=CC21 Chemical compound C1=CC=CC=2C=CC=3C=4C=CC=CC4NC3C21.C2(=CC=CC1=CC=CC=C21)N2C1=CC=CC=C1C=1C=CC=CC21 JTPHKHUWLNQSSU-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 241000720974 Protium Species 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 101000766357 Ruditapes philippinarum Big defensin Proteins 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical group C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 1
- 125000005577 anthracene group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- LPTWEDZIPSKWDG-UHFFFAOYSA-N benzenesulfonic acid;dodecane Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCCCCCCCCCCC LPTWEDZIPSKWDG-UHFFFAOYSA-N 0.000 description 1
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 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
- 150000001716 carbazoles Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
- 229960005544 indolocarbazole Drugs 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 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
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 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
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition 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
- 125000005579 tetracene group Chemical group 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 125000005556 thienylene group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- 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
- C07D471/04—Ortho-condensed systems
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- 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
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
- H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
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- H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
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- Electroluminescent Light Sources (AREA)
Abstract
The invention relates to a compound and application thereof, wherein the compound has a structure shown in a formula I, is a red phosphorescent main body material containing diarylamine, can effectively improve the hole transport performance of the main body material, and can effectively improve the hole transport performance of the main body material when being applied to an OLED (organic light emitting diode) deviceThe organic electroluminescent material has high efficiency and low driving voltage, and is one excellent main body material, especially one excellent red light main body material.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a compound and application thereof.
Background
In recent years, Organic Light Emitting Diodes (OLEDs) have been developed very rapidly, and have a place in the field of information display, which is mainly benefited from the fact that OLED devices can prepare full-color display devices using three primary colors of high saturation, red, green and blue, and can realize bright, light, thin and soft colors without additional backlight sources.
The Organic Light Emitting Diode (OLED) device plays an important role in a thin-layer structure containing various organic functional materials, and common organic functional materials comprise a light emitting layer material, an electron blocking layer material, an electron transport layer material, a hole blocking layer material, a hole transport layer material and the like. After the power is switched on, electrons and holes are respectively injected and transmitted to the light-emitting layer and are recombined to generate excitons, so that light is emitted. Therefore, the research on organic functional materials in OLED devices is a key research topic for those skilled in the art.
At present, researchers have developed various organic functional materials for various specific device structures, which play roles in improving carrier mobility, regulating carrier balance, breaking through electroluminescence efficiency, and delaying device attenuation.
Conventional fluorescent emitters emit light primarily using singlet excitons generated upon recombination of holes and electrons, and such emitters are still used in various OLED devices. In addition, a phosphorescent emitter, that is, a material which can emit light by using both triplet excitons and singlet excitons, such as an iridium complex or the like, is also included. Most importantly, the thermal excitation delayed fluorescence (TADF) technology can still effectively utilize triplet excitons to realize higher luminous efficiency by promoting the conversion of the triplet excitons to the singlet excitons without adopting a metal complex, and the thermal excitation sensitized fluorescence (TASF) technology is to adopt a TADF material to sensitize a luminous body in an energy transfer manner to realize higher luminous efficiency, so that the TADF material has a wide application prospect in the field of OLEDs.
Although various organic functional layer materials have been developed, nowadays, the requirements of people on the performance of the OLED device are higher and higher, and the existing organic functional materials cannot be applied to new OLED devices with higher performance.
Therefore, there is a need in the art to develop a wider variety of organic functional materials, which can improve the light emitting efficiency, reduce the driving voltage, and prolong the service life when applied to OLED devices.
Disclosure of Invention
In view of the deficiencies of the prior art, it is an object of the present invention to provide a compound. When the compound is applied to an OLED device, the luminous efficiency can be improved, the driving voltage can be reduced, and the service life can be prolonged.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention provides a compound, which has a structure shown in a formula I;
in the formula I, A is selected from structures shown in a formula (a) or a formula (b);
when A is a structure represented by the formula (a), Ar1Is a substituted or unsubstituted C3-C30 heteroaryl group, wherein the heteroatom is N, O, S, P, Si; when A is a structure represented by the formula (b), Ar1Is a substituted or unsubstituted heteroaryl group of C3-C30, wherein the heteroatom is N, O, P, Si and when the heteroatom is N, the Ar is1Contains at least two N atoms;
said X1、X2、X3、X4Each independently selected from N or CR, R is selected from one of hydrogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, silyl, amino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroaryl amino and substituted or unsubstituted C3-C30 heteroaryl, and when a plurality of R are adopted, adjacent R can be mutually bonded to form C6-C30 aryl or C4-C30 heteroaryl;
said L1One selected from single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene;
in the formula (a), Ar is2、Ar3、Ar4Each independently selected from one of substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
L2selected from single bonds, substituted or notOne of substituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene;
L3one selected from substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene;
in the formula (b), Ar5、Ar6、Ar7、Ar8Each independently selected from one of substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
L4one selected from substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene;
when the substituent group exists in the groups, the substituent group is selected from one or a combination of at least two of halogen, cyano, carbonyl, chain alkyl of C1-C20, cycloalkyl of C3-C20, alkenyl of C2-C10, alkoxy or thioalkoxy of C1-C10, arylamino of C6-C30, heteroarylamino of C3-C30, aryl of C6-C30 and heteroaryl of C3-C30.
Preferably, in formula I, Ar1Is substituted or unsubstituted C3-C30 heteroaryl, wherein the heteroatom is N.
Still preferably, in the formula I, when A is a structure represented by the formula (a), Ar1Selected from the following substituted or unsubstituted groups:
when A is a structure represented by the formula (b), Ar1Selected from the following substituted or unsubstituted groups:
when the substituent group exists in the groups, the substituent group is selected from one or a combination of at least two of halogen, cyano, carbonyl, chain alkyl of C1-C12, cycloalkyl of C3-C12, alkenyl of C2-C10, alkoxy or thioalkoxy of C1-C10, arylamino of C6-C30, heteroarylamino of C3-C30, aryl of C6-C30 and heteroaryl of C3-C30.
Preferably, in the formula I, L is1Selected from the group consisting of a single bond, phenylene, biphenylene, terphenylene, naphthylene, furanylene, thiophenylene, pyridinylene, pyrimidinylene, or triazinylene;
in the formula (a), L2Selected from the group consisting of a single bond, phenylene, biphenylene, terphenylene, naphthylene, furylene and thienylene, and L3Selected from phenylene, biphenylene, terphenylene, naphthylene, furanylene or thiophenylene;
in the formula (b), L4Selected from phenylene, biphenylene, terphenylene, naphthylene, furan or thiophenylene.
Preferably, in formula I, X1、X2、X3、X4Each independently selected from CR, R is selected from one of hydrogen, C1-C5 chain alkyl, C3-C5 cycloalkyl, C1-C5 alkoxy, halogen, cyano, C6-C30 aryl, C6-C30 arylamino, C3-C30 heteroaryl amino and C3-C30 heteroaryl; preferably, R is hydrogen;
or, in formula I, X1、X2、X3、X4One of them is N, X1、X2、X3、X4Three of the compounds are respectively and independently selected from CR, R is selected from one of hydrogen, C1-C5 chain alkyl, C3-C5 cycloalkyl, C1-C5 alkoxy, halogen, cyano, C6-C30 aryl, C6-C30 arylamino, C3-C30 heteroaryl amino and C3-C30 heteroaryl; preferably, R is hydrogen.
More preferably, in formula (a), Ar is2、Ar3、Ar4Each independently selected from phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, anthryl, perylenyl, anthryl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, trimeric indenyl, isotridecyl, spiromesitylTriindenyl, spiroiso-triindenyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxaloiyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthraoxazolyl, phenanthroizolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzpyridazinyl, One of pyrimidinyl, benzopyrimidinyl and quinoxalinyl;
in the formula (b), Ar is5、Ar6、Ar7、Ar8Each independently selected from phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthrenyl, benzophenanthrenyl, pyrenyl, bornyl, perylenyl, fluoranthenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, idophenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, triindenyl, isotridendenyl, spiroisotridendenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolinyl, benzo-6, 7-quinolinyl, benzo-7, 8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalimidazolyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthracenooxazolyl, phenanthroioxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyrazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl.
Most preferably, formula (VI)(a) In (1), Ar2、Ar3、Ar4Each independently selected from one of phenyl, naphthyl, phenanthryl, biphenyl, terphenyl, fluorenyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl and carbazolyl;
in the formula (b), Ar is5、Ar6、Ar7、Ar8Each independently selected from one of phenyl, naphthyl, phenanthryl, biphenyl, terphenyl, fluorenyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, carbazolyl.
The above "substituted or unsubstituted" group may be substituted with one substituent, or may be substituted with a plurality of substituents, and when a plurality of substituents are present, different substituents may be selected.
In the present invention, the expression of Ca to Cb means that the group has carbon atoms of a to b, and the carbon atoms do not generally include the carbon atoms of the substituents unless otherwise specified.
In the present invention, the expression of chemical elements includes the concept of chemically identical isotopes, for example, hydrogen (H) includes1H (protium or H),2H (deuterium or D), etc.; carbon (C) then comprises12C、13C and the like.
The above-mentioned C1-C20 chain alkyl group is preferably a C1-C10 chain alkyl group, and more preferably a C1-C5 chain alkyl group. Examples thereof include: methyl, ethyl, n-propyl, n-butyl, n-hexyl, n-octyl, isopropyl, isobutyl, tert-butyl and the like.
The above-mentioned C3-C30 cycloalkyl group is preferably C3-C20 cycloalkyl group, more preferably C3-C10 cycloalkyl group, and still more preferably cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, adamantyl group or the like.
In the present invention, the C6-C30 aryl group includes C6-C30 monocyclic aryl group or C10-C30 fused ring aryl group, wherein monocyclic aryl group means that the aromatic ring exists as a single ring, no fusion exists, and includes, but is not limited to, phenyl, biphenyl, or terphenyl group; a fused ring aryl refers to a structure in which at least two aromatic rings are fused, including, but not limited to, naphthyl, anthryl, phenanthryl, fluorenyl, and the like.
In the present invention, the C6-C30 arylamino represents a group formed by substituting one or two C6-C30 aryl groups for hydrogen on an amino group, wherein the linking site of the C6-C30 arylamino group can be linked to an aryl group in the arylamino group or can be linked to N in the arylamino group, and exemplary carbon numbers and specific groups of the C6-C30 aryl group in the C6-C30 arylamino group are the same as those described above.
In the present invention, the heteroaryl group of C3-C30 includes C3-C30 monocyclic heteroaryl group or C6-C30 fused ring heteroaryl group, wherein the monocyclic heteroaryl group means that the heteroaryl ring exists in the form of a single ring without fusion, including but not limited to furan, thiophene, pyridine, pyrimidine, triazine, or a group formed by connecting at least two thereof, etc.; fused heteroaryl refers to a fused ring aryl group containing a heteroatom, including but not limited to a dibenzofuran group, a dibenzothiophene group, or a carbazole group, and the like.
In the present invention, the heteroaryl amino group having C3-C30 represents a group formed by substituting one or two C3-C30 heteroaryl groups for hydrogen on the amino group, wherein the linking site of the C3-C30 heteroaryl amino group can be linked to the heteroaryl group in the heteroaryl amino group or linked to N in the heteroaryl amino group, and exemplary numbers of carbons and specific groups of the C3-C30 heteroaryl group in the C3-C30 heteroaryl amino group are the same as those described above.
The substituted or unsubstituted C6-C30 aryl group, preferably C6-C30 aryl group, preferably the aryl group is selected from phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl and derivatives thereof, fluoranthyl, triphenylenyl, pyrenyl, perylenyl, perylene, and the like,
A group of the group consisting of a phenyl group and a tetracenyl group. The biphenyl group is selected from the group consisting of 2-biphenyl, 3-biphenyl, and 4-biphenyl; the terphenyl group includes p-terphenyl-4-yl, p-terphenyl-3-ylP-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes a 1-naphthyl group or a 2-naphthyl group; the anthracene group is selected from the group consisting of 1-anthracene group, 2-anthracene group, and 9-anthracene group; the fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl; the fluorenyl derivative is selected from the group consisting of 9, 9-dimethylfluorene, 9-spirobifluorene and benzofluorene; the pyrenyl group is selected from the group consisting of 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetracene group is selected from the group consisting of 1-tetracene, 2-tetracene, and 9-tetracene.
The substituted or unsubstituted C3-C30 heteroaryl group, preferably C3-C30 heteroaryl group, preferably the heteroaryl group is furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, isobenzofuryl, indolyl, dibenzofuryl, dibenzothienyl, carbazolyl and derivatives thereof, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole benzocarbazole, dibenzocarbazole, or indolocarbazole.
Preferably, the compound has any one of the structures described below as P1-P104:
a second object of the present invention is to provide an application of the compound according to the first object as a functional material in an organic electronic device including an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information tag, an electronic artificial skin sheet, a sheet type scanner, or electronic paper;
preferably, the compound is applied to an organic electroluminescent device, preferably a red organic electroluminescent device.
More preferably, the compound is used as a host material of the organic electroluminescent device, preferably as a red host material.
It is a further object of the present invention to provide an organic electroluminescent device comprising a first electrode, a second electrode and a plurality of light-emitting functional layers interposed between the first electrode and the second electrode, the light-emitting functional layers containing at least one compound according to one of the objects.
Preferably, the light-emitting functional layer includes a light-emitting layer containing at least one compound described for one of the purposes.
Preferably, the light-emitting layer includes a host material and a dopant material, and the host material includes at least one compound described for one of the purposes.
In one embodiment, the light emitting functional layer may further include a hole transport region and an electron transport region.
In one embodiment, a substrate may be used below the first electrode or above the second electrode. The substrate is a glass or polymer material having excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode may be formed by sputtering or depositing a material used as the first electrode on the substrate. When the first electrode is used as an anode, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO) may be used2) Oxide transparent conductive materials such as zinc oxide (ZnO), and any combination thereof. When the first electrode is used as a cathode, a metal or an alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof can be used.
The light-emitting functional layer can be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compounds used as the light emitting functional layer may be small organic molecules, large organic molecules, and polymers, and combinations thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer containing only one compound and a single layer containing a plurality of compounds. The hole transport region may also be a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL).
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylenevinylene, polyaniline/dodecylbenzene sulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives including compounds shown below as HT-1 to HT-50; or any combination thereof.
The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more compounds of HT-1 to HT-50 described above, or one or more compounds of HI-1 to HI-3 described below; one or more of the compounds HT-1 to HT-50 may also be used to dope one or more of the compounds HI-1 to HI-3 described below.
The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra, and may also include a Host material (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The single color light emitting layers of a plurality of different colors may be arranged in a planar manner in accordance with a pixel pattern, or may be stacked to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light-emitting layer may be a single color light-emitting layer capable of emitting red, green, blue, or the like at the same time.
According to different technologies, the luminescent layer material can be different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescent luminescent material, and the like. In an OLED device, a single light emitting technology may be used, or a combination of a plurality of different light emitting technologies may be used. These technically classified different luminescent materials may emit light of the same color or of different colors.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescent technology. The phosphorescent dopant of the light emitting layer thereof may be selected from, but not limited to, a combination of one or more of RPD-1 to RPD-28 listed below.
The electron transport region may be an Electron Transport Layer (ETL) of a single-layer structure including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
In one aspect of the invention, the electron transport layer material may be selected from, but is not limited to, the combination of one or more of ET-1 through ET-73 listed below.
An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer materials including, but not limited to, combinations of one or more of the following.
Liq、LiF、NaCl、CsF、Li2O、Cs2CO3、BaO、Na、Li、Ca、Yb。
The cathode is metal, metal mixture or oxide such as magnesium silver mixture, LiF/Al, ITO, etc.
The specific reason why the compound of the present invention has excellent properties is not clear, and it is presumed that the following reasons may be mentioned:
the compound provided by the invention is a carbazole derivative containing diarylamine, and the substitution site is fixed at the 3-position of carbazole, so that on one hand, a diarylamine group has good hole transport performance, the voltage of a device can be effectively reduced, and the efficiency is improved; on the other hand, the 3-position of carbazole has high electric-rich property and is easy to generate electrophilic reaction, and due to the existence of a complex electrochemical environment in a device, if naked active hydrogen exists on the 3-position of carbazole, the reaction is easy to generate, so that the service life of the device is influenced, so that the 3-position of carbazole is substituted, and compared with compounds substituted at other positions of carbazole, the compound provided by the invention has longer service life. The compound provided by the invention can be used as a good luminescent host material, in particular to a good red light host material.
Detailed Description
For the purpose of facilitating an understanding of the present invention, the present invention will now be described by way of examples. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitation of the present invention.
The compounds of formula I of the present invention represent the synthetic route as follows:
the above symbols all have the same meaning as in formula I.
Synthesis example 1:
synthesis of Compound P2
Adding 3-bromocarbazole (100mmol), 2-chloro-4-phenylquinazoline (110mmol), cesium carbonate (150mmol) and 200mL of N, N-dimethylformamide into a reaction bottle, heating to 150 ℃ for reacting for 4h, monitoring by TLC to complete reaction, cooling, pouring the reaction into water, filtering, and recrystallizing with xylene to obtain P2-A.
Adding N1- ([1,1 '-biphenyl ] -4-yl-N1- (4-bromophenyl) -N4, N4-diphenyl-1, 4-diphenylamine (100mmol), pinacol diboron (120mmol), potassium acetate (150mmol), [1,1' -bis (diphenylphosphine) ferrocene ] palladium dichloride (1.2mmol) and dioxane 200ml into a reaction bottle, carrying out reflux reaction for 4 hours under the protection of nitrogen, adding water and dichloromethane for extraction after complete reaction, concentrating an organic phase, and carrying out column chromatography purification to obtain P2-B.
Adding P2-A (50mmol), P2-B (55mmol), potassium carbonate (80mmol), tetrakis (triphenylphosphine) palladium (0.5mmol), water (30mL) and 300mL of dioxane into a reaction bottle, heating to 120 ℃ for reacting for 6h, monitoring the reaction by TLC, adding water and dichloromethane for extraction, separating an organic phase, concentrating, and purifying by column chromatography to obtain P2. Mass spectrum (M/Z): 858.4.
synthesis example 2:
synthesis of Compound P10
The difference from synthetic example 1 is that N1- ([1,1' -biphenyl)]-4-yl-N1- (4-bromophenyl) -N4, N4-diphenyl-1, 4-diphenylamine in an amount equivalent to N1- (4-bromophenyl) -N1- (dibenzofuran-2-yl) -N4,N4Diphenyl-1, 4-diphenylamine to give the compound P10. Mass spectrum (M/Z): 872.3.
synthesis example 3:
synthesis of Compound P26
Adding P2-A (50mmol), N4, N4, N6-triphenyl dibenzofuran-4, 6-diphenylamine (50mmol), sodium tert-butoxide (80mmol), tris (dibenzylideneacetone) dipalladium (0.05mmol), 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (0.1mmol, S-Phos) and toluene (200ml) into a reaction bottle, heating to 120 ℃ for reaction for 7 hours, monitoring the reaction by TLC, cooling, adding water and dichloromethane for extraction, concentrating an organic phase, and purifying by column chromatography to obtain P26. Mass spectrum (M/Z): 796.3.
synthesis example 4:
synthesis of Compound P54
Adding 3-bromocarbazole (100mmol), 2-chloro-3-phenylquinoxaline (110mmol), cesium carbonate (150mmol) and 200mL of N, N-dimethylformamide into a reaction bottle, heating to 150 ℃ for reacting for 4h, monitoring by TLC to complete the reaction, cooling, pouring the reaction into water, filtering, and recrystallizing xylene to obtain P54-A.
Adding P54-A (50mmol), S1(50mmol), sodium tert-butoxide (80mmol), tris (dibenzylideneacetone) dipalladium (0.05mmol), 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (0.1mmol, S-Phos) and toluene (200ml) into a reaction bottle, heating to 120 ℃ for reaction for 5h, monitoring the reaction by TLC, cooling, adding water and dichloromethane for extraction, concentrating an organic phase, and purifying by column chromatography to obtain P54. Mass spectrum (M/Z): 858.4.
synthesis example 5:
synthesis of Compound P59
The difference from Synthesis example 4 was that S1 was replaced with N2, N2, N6-triphenyl-naphthalene-2, 6-diphenylamine in equal amounts to obtain P59. Mass spectrum (M/Z): 756.3.
synthesis example 6:
synthesis of Compound P69
Adding 3-bromocarbazole (100mmol), 2- (2-fluorophenyl) -4, 6-diphenyl 1,3,5 triazine (110mmol), cesium carbonate (150mmol) and 200mL of N, N-dimethylformamide into a reaction bottle, heating to 150 ℃ for reacting for 4h, monitoring the reaction by TLC (thin layer chromatography), cooling, pouring the reaction into water, filtering, and recrystallizing xylene to obtain P69-A.
Adding P69-A (50mmol), N, N, N-triphenyl-1, 4-phenylenediamine (50mmol), sodium tert-butoxide (80mmol), tris (dibenzylideneacetone) dipalladium (0.05mmol), 2-dicyclohexylphosphine-2 ',6' -dimethoxybiphenyl (0.1mmol, S-Phos) and toluene (200ml) into a reaction bottle, heating to 120 ℃ for reaction for 5h, monitoring the reaction by TLC, cooling, adding water and dichloromethane for extraction, concentrating an organic phase, and purifying by column chromatography to obtain P69. Mass spectrum (M/Z): 809.3.
synthesis example 7:
synthesis of Compound P78
The difference from Synthesis example 1 is that N1- ([1,1' -biphenyl ] -4-yl-N1- (4-bromophenyl) -N4, N4-diphenyl-1, 4-diphenylamine was replaced with 5-bromo-N, N, N ', N ' -tetraphenyl-benzene-1, 3-diamine in the same amount as N, to give compound P78. Mass Spectrum (M/Z): 782.3.
Synthesis example 8:
synthesis of Compound P93
Adding 8-bromo-5H-pyrido [3,2-B ] indole (100mmol), 2-chloro-4-phenylquinazoline (110mmol), cesium carbonate (150mmol) and 200mL of N, N-dimethylformamide into a reaction bottle, heating to 150 ℃ for reacting for 4H, monitoring by TLC to complete reaction, cooling, pouring the reaction into water, filtering, and recrystallizing xylene to obtain P93-A.
Adding S2(100mmol), pinacol diboride (120mmol), potassium acetate (150mmol), [1,1' -bis (diphenylphosphino) ferrocene ] palladium dichloride (1.2mmol) and dioxane (200ml) into a reaction bottle, refluxing and reacting for 4 hours under the protection of nitrogen, adding water and dichloromethane after complete reaction for extraction, concentrating an organic phase, and purifying by column chromatography to obtain P93-B.
Adding P93-A (50mmol), P93-B (55mmol), potassium carbonate (80mmol), tetrakis (triphenylphosphine) palladium (0.5mmol), water (30mL) and 300mL of dioxane into a reaction bottle, heating to 120 ℃ for reacting for 6h, monitoring the reaction by TLC, adding water and dichloromethane for extraction, separating an organic phase, concentrating, and purifying by column chromatography to obtain P93. Mass spectrum (M/Z): 935.4.
synthesis example 9:
synthesis of Compound P101
The difference from Synthesis example 4 was that 3-bromocarbazole was replaced with 8-bromo-5H-pyrido [4,3-B ] indole in an equivalent amount to give Compound P101. Mass spectrum (M/Z): 859.4.
the present invention exemplarily provides specific synthetic methods for the above compounds, and the compounds that are not provided with specific synthetic methods in the following examples are also prepared by similar methods, and can be obtained only by replacing raw materials, which are not described herein again, or can be prepared by other methods in the prior art by those skilled in the art.
Examples 1 to 10 and comparative examples 1 to 2
The above examples and comparative examples respectively provide an organic electroluminescent device, and the specific preparation method is as follows:
the glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
placing the glass substrate with the ITO anode in a vacuum chamber, and vacuumizing to<1×10-5Pa, performing vacuum thermal evaporation on the anode layer film in sequence to obtain a 10nm HT-4: HI-3(97/3, w/w) mixture as a hole injection layer; 60nm of compound HT-4 as hole transport layer; by vacuum evaporation of a compound HT-47 as a device on top of the hole transport layerThe evaporation rate of the electron barrier layer material is 0.1nm/s, and the total film thickness of the evaporation is 60 nm; host material of 40 nm: an RPD-8(100:3, w/w) binary mixture as a light-emitting layer; vacuum evaporating 5nm of ET-17 on the light-emitting layer to be used as a hole blocking layer of the device; a 25nm mixture of compounds ET-69: ET-57(50/50, w/w) as an electron transport layer; LiF with the particle size of 1nm is used as an electron injection layer; 150nm of metallic aluminum as a cathode.
The host in the light-emitting layer was each of the compounds listed in table 1. The total evaporation rate of all the organic layers and LiF is controlled at 0.1nm/s, and the evaporation rate of the metal electrode is controlled at 1 nm/s.
The compound C1 is described in detail in patent application KR1020130024521A, and the compound C2 is described in patent application WO2012043996A 2.
And (3) performance testing:
the organic electroluminescent devices prepared in examples and comparative examples were measured for driving voltage and current efficiency at the same brightness. Specifically, the voltage was raised at a rate of 0.1V per second, and it was determined that the luminance of the organic electroluminescent device reached 3000cd/m2The current density is measured at the same time as the driving voltage; the ratio of the brightness to the current density is the current efficiency; taking the current efficiency of the comparative example 1 as 1, the voltage as 1, and the ratio of the rest to the comparative example 1; the lifetime test was set to 10000cd/m of initial luminance2Then, its luminance is attenuated to 9800cd/m2The required time, C1 in comparative example 1 was set to have a lifetime of 1, the remainder being the ratio to comparative example 1.
The results of device performance tests of each of the examples and comparative examples prepared above are shown in table 1.
Table 1:
as can be seen from table 1, the compound provided by the present invention as a light emitting host material of a device can improve the efficiency of the device, reduce the driving voltage, and increase the lifetime of the device.
The difference of the molecular structure of the compound C1 in the prior art and the compound of the invention is that the substitution sites on the carbazole group are different, the diarylamine structure in the compound C1 is connected to the 2-position of the mother-nucleus carbazole group, the molecular structure may cause the instability of the compound in a complex electrochemical environment, and the diarylamine structure in the compound of the invention is connected to the 3-position of the mother-nucleus carbazole group, so that the problem that the service life of the device is influenced because the electrophilic reaction is easy to occur if 3-position exposed active hydrogen is avoided. As can be seen from the data in Table 1 above, the device lifetimes of examples 1-10, which were prepared using the compounds of the present invention as the luminescent host, were all greater than the device lifetime of comparative example 1, which was prepared using C1 as the luminescent host. The molecular structure of the compound C2 in the prior art differs from that of the compound of the present invention in that a monoaza group is used in the molecule C2 to connect the N atom of the carbazole group as an electron-deficient group, and as can be seen from the data in table 1 above, the device of comparative example 2 prepared using C2 as a light-emitting host material has the effect that the voltage is relatively higher than the voltage of the devices of examples 1 to 10 prepared using the compound of the present invention as a light-emitting host material, and the efficiency exhibited by the device of comparative example 2 is also poor because the molecular structure of C2 causes the imbalance of electron and hole transport in the device, both of which are significantly lower than the efficiency of the devices of examples 1 to 10.
The applicant states that the present invention is illustrated in detail by the above examples, but the present invention is not limited to the above detailed methods, i.e. it is not meant that the present invention must rely on the above detailed methods for its implementation. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
Claims (9)
1. A compound of the general formula having the structure shown in formula I:
in the formula I, A is selected from structures shown in a formula (a) or a formula (b);
when A is a structure represented by the formula (a), Ar1Is a substituted or unsubstituted C3-C30 heteroaryl group, wherein the heteroatom is N, O, S, P, Si;
when A is a structure represented by the formula (b), Ar1Is a substituted or unsubstituted heteroaryl group of C3-C30, wherein the heteroatom is N, O, P, Si and when the heteroatom is N, the Ar is1Contains at least two N atoms;
said X1、X2、X3、X4Each independently selected from N or CR, R is selected from one of hydrogen, C1-C10 chain alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, silyl, amino, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroaryl amino and substituted or unsubstituted C3-C30 heteroaryl, and when a plurality of R are adopted, adjacent R can be mutually bonded to form C6-C30 aryl or C4-C30 heteroaryl;
said L1One selected from single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene;
in the formula (a), Ar is2、Ar3、Ar4Each independently selected from substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
L2one selected from single bond, substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene;
L3selected from substituted or unsubstituted C6-C30 aryleneOne of substituted or unsubstituted C3-C30 heteroarylene;
in the formula (b), Ar is5、Ar6、Ar7、Ar8Each independently selected from one of substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl;
L4one selected from substituted or unsubstituted C6-C30 arylene, substituted or unsubstituted C3-C30 heteroarylene;
when the substituent group exists in the groups, the substituent group is selected from one or a combination of at least two of halogen, cyano, carbonyl, chain alkyl of C1-C20, cycloalkyl of C3-C20, alkenyl of C2-C10, alkoxy or thioalkoxy of C1-C10, arylamino of C6-C30, heteroarylamino of C3-C30, aryl of C6-C30 and heteroaryl of C3-C30.
2. A compound of claim 1, formula I, wherein Ar1Is substituted or unsubstituted C3-C30 heteroaryl, wherein the heteroatom is N.
3. The compound of claim 1, wherein:
when A is a structure represented by the formula (a), Ar1Selected from the following substituted or unsubstituted groups:
when A is a structure represented by the formula (b), Ar1Selected from the following substituted or unsubstituted groups:
when the substituent group exists in the groups, the substituent group is selected from one or a combination of at least two of halogen, cyano, carbonyl, chain alkyl of C1-C12, cycloalkyl of C3-C12, alkenyl of C2-C10, alkoxy or thioalkoxy of C1-C10, arylamino of C6-C30, heteroarylamino of C3-C30, aryl of C6-C30 and heteroaryl of C3-C30.
4. The compound of claim 1, formula i wherein L1Selected from the group consisting of a single bond, phenylene, biphenylene, terphenylene, naphthylene, furanylene, thiophenylene, pyridinylene, pyrimidinylene, or triazinylene;
in the formula (a), L2Selected from the group consisting of a single bond, phenylene, biphenylene, terphenylene, naphthylene, furanylene, or thiophenylene, and L3Selected from phenylene, biphenylene, terphenylene, naphthylene, furanylene or thiophenylene;
in the formula (b), L4Selected from phenylene, biphenylene, terphenylene, naphthylene, furan or thiophenylene.
5. A compound of claim 1, formula I wherein X1、X2、X3、X4Each independently selected from CR, R is selected from one of hydrogen, C1-C5 chain alkyl, C3-C5 cycloalkyl, C1-C5 alkoxy, halogen, cyano, C6-C30 aryl, C6-C30 arylamino, C3-C30 heteroaryl amino and C3-C30 heteroaryl; preferably, R is hydrogen;
or, in formula I, X1、X2、X3、X4One of them is N, X1、X2、X3、X4Three of the compounds are respectively and independently selected from CR, R is selected from one of hydrogen, C1-C5 chain alkyl, C3-C5 cycloalkyl, C1-C5 alkoxy, halogen, cyano, C6-C30 aryl, C6-C30 arylamino, C3-C30 heteroarylamino and C3-C30 heteroaryl; preferably, R is hydrogen.
6. The compound of claim 1, formula (a), wherein Ar is2、Ar3、Ar4Each independently selected from phenyl, naphthyl, anthryl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl and cavernylAn perylene group, a fluoranthenyl group, a tetracenyl group, a pentacenyl group, a benzopyrenyl group, a biphenyl group, an idophenyl group, a terphenyl group, a quaterphenyl group, a fluorenyl group, a spirobifluorenyl group, a dihydrophenanthryl group, a dihydropyrenyl group, a tetrahydropyrenyl group, a cis-or trans-indenofluorenyl group, a trimeric indenyl group, an isotridecyl group, a spirotrimeric indenyl group, a spiroisotridecyl group, a furanyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a thienyl group, a benzothienyl group, an isobenzothienyl group, a dibenzothienyl group, a pyrrolyl group, an isoindolyl group, a carbazolyl group, an indenocarbazolyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, an acridinyl group, a phenanthridinyl group, a benzo-5, 6-quinolyl group, a benzo-6, 7-quinolyl group, a benzo-7, 8-quinolyl group, a pyrazolyl group, an indazolyl group, an imidazolyl group, a benzimidazolyl group, a naphthoimidazolyl group, a salt, One of phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxaloimidazolyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthracenooxazolyl, phenanthroizolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyrazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl;
in the formula (b), Ar is5、Ar6、Ar7、Ar8Each independently selected from phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthrenyl, benzophenanthrenyl, pyrenyl, bornyl, perylenyl, fluoranthenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, idophenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, triindenyl, isotridendenyl, spiroisotridendenyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolinyl, benzo-6, 7-quinolinyl, benzo-7, 8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthrimidazolyl, pyridoimidazolyl, pyrazinimidazolyl, quinoxalimidazolyl, oxazolylOne of benzoxazolyl, naphthooxazolyl, anthracenooxazolyl, phenanthrenooxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl and quinoxalinyl;
preferably, in the formula (a), Ar is2、Ar3、Ar4Each independently selected from one of phenyl, naphthyl, phenanthryl, biphenyl, terphenyl, fluorenyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl and carbazolyl;
in the formula (b), Ar5、Ar6、Ar7、Ar8Each independently selected from one of phenyl, naphthyl, phenanthryl, biphenyl, terphenyl, fluorenyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, carbazolyl.
7. The compound of claim 1, having the structure shown below:
8. use of a compound according to any one of claims 1 to 7 as a functional material in an organic electronic device comprising an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information label, an electronic artificial skin sheet, a sheet-type scanner or electronic paper;
preferably, the compound is applied to be used as a luminescent layer material in an organic electroluminescent device;
more preferably, the compound is applied to be used as a host material of a red light emitting layer in an organic electroluminescent device.
9. An organic electroluminescent device comprising a first electrode, a second electrode and one or more light-emitting functional layers interposed between the first electrode and the second electrode, wherein the light-emitting functional layers contain the compound according to any one of claims 1 to 7;
preferably, the light-emitting functional layer includes a light-emitting layer containing the compound according to any one of claims 1 to 7;
more preferably, the light-emitting layer includes a host material and a dopant material, and the host material includes at least one compound described for one of the purposes.
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Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101855315A (en) * | 2007-11-08 | 2010-10-06 | Lg化学株式会社 | New compound and organic light emitting device using the same |
| WO2012043996A2 (en) * | 2010-09-30 | 2012-04-05 | 덕산하이메탈(주) | Compound in which amine derivative is substituted with fluorene, organic electronic device using same, and terminal thereof |
| US20140138627A1 (en) * | 2012-11-20 | 2014-05-22 | Universal Display Corporation | Organic Electroluminescent Device With Delayed Fluorescence |
| CN103827257A (en) * | 2012-02-27 | 2014-05-28 | 株式会社Lg化学 | Organic light emitting diode |
| KR20150068282A (en) * | 2013-12-09 | 2015-06-19 | 주식회사 엠비케이 | Novel organic electroluminescent compound, organic electroluminescent device including the same and electric apparatus |
| CN107787314A (en) * | 2015-06-12 | 2018-03-09 | 德山新勒克斯有限公司 | Organic electric element compound, organic electric element and its electronic installation using it |
| US20200020863A1 (en) * | 2016-09-22 | 2020-01-16 | Duk San Neolux Co., Ltd | Compound for organic electronic element, organic electronic element using same and electronic device therefor |
| WO2020116816A1 (en) * | 2018-12-06 | 2020-06-11 | 덕산네오룩스 주식회사 | Compound for organic electric element, organic electric element using same, and electronic device comprising organic electric element |
| KR20200081771A (en) * | 2018-12-28 | 2020-07-08 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
-
2020
- 2020-11-18 CN CN202011291799.6A patent/CN114516859A/en active Pending
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101855315A (en) * | 2007-11-08 | 2010-10-06 | Lg化学株式会社 | New compound and organic light emitting device using the same |
| WO2012043996A2 (en) * | 2010-09-30 | 2012-04-05 | 덕산하이메탈(주) | Compound in which amine derivative is substituted with fluorene, organic electronic device using same, and terminal thereof |
| CN103827257A (en) * | 2012-02-27 | 2014-05-28 | 株式会社Lg化学 | Organic light emitting diode |
| US20140138627A1 (en) * | 2012-11-20 | 2014-05-22 | Universal Display Corporation | Organic Electroluminescent Device With Delayed Fluorescence |
| KR20150068282A (en) * | 2013-12-09 | 2015-06-19 | 주식회사 엠비케이 | Novel organic electroluminescent compound, organic electroluminescent device including the same and electric apparatus |
| CN107787314A (en) * | 2015-06-12 | 2018-03-09 | 德山新勒克斯有限公司 | Organic electric element compound, organic electric element and its electronic installation using it |
| US20200020863A1 (en) * | 2016-09-22 | 2020-01-16 | Duk San Neolux Co., Ltd | Compound for organic electronic element, organic electronic element using same and electronic device therefor |
| WO2020116816A1 (en) * | 2018-12-06 | 2020-06-11 | 덕산네오룩스 주식회사 | Compound for organic electric element, organic electric element using same, and electronic device comprising organic electric element |
| KR20200081771A (en) * | 2018-12-28 | 2020-07-08 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
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