CN107840835A - New heterocyclic compound and utilize its organic illuminating element - Google Patents
New heterocyclic compound and utilize its organic illuminating element Download PDFInfo
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- CN107840835A CN107840835A CN201710623704.8A CN201710623704A CN107840835A CN 107840835 A CN107840835 A CN 107840835A CN 201710623704 A CN201710623704 A CN 201710623704A CN 107840835 A CN107840835 A CN 107840835A
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- 150000002391 heterocyclic compounds Chemical class 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 77
- 239000000126 substance Substances 0.000 claims description 61
- -1 biphenyl -4,4 '-diyl Chemical group 0.000 claims description 53
- 239000011368 organic material Substances 0.000 claims description 41
- 238000002347 injection Methods 0.000 claims description 38
- 239000007924 injection Substances 0.000 claims description 38
- 230000005540 biological transmission Effects 0.000 claims description 21
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 238000006467 substitution reaction Methods 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 229910052710 silicon Inorganic materials 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002019 doping agent Substances 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 230000005611 electricity Effects 0.000 claims description 3
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims 1
- 125000005104 aryl silyl group Chemical group 0.000 claims 1
- 239000010410 layer Substances 0.000 description 129
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- 238000006243 chemical reaction Methods 0.000 description 19
- 238000000034 method Methods 0.000 description 19
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- 230000014509 gene expression Effects 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 0 C[C@@](CC=CC=CC=[I+])[C@@](C)(*C(*)C1IC=CC=*1)C(C)=CC Chemical compound C[C@@](CC=CC=CC=[I+])[C@@](C)(*C(*)C1IC=CC=*1)C(C)=CC 0.000 description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
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- 239000010406 cathode material Substances 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
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- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 229960003540 oxyquinoline Drugs 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 3
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- 125000002877 alkyl aryl group Chemical group 0.000 description 3
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- 125000005018 aryl alkenyl group Chemical group 0.000 description 3
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- 150000004696 coordination complex Chemical class 0.000 description 3
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- 150000004826 dibenzofurans Chemical class 0.000 description 3
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical class C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 125000005264 aryl amine group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 229920001940 conductive polymer Polymers 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 2
- 229910052733 gallium Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 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 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000003475 lamination Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 238000005240 physical vapour deposition Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
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- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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- 125000001425 triazolyl group Chemical group 0.000 description 2
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
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- UWRZIZXBOLBCON-VOTSOKGWSA-N (e)-2-phenylethenamine Chemical compound N\C=C\C1=CC=CC=C1 UWRZIZXBOLBCON-VOTSOKGWSA-N 0.000 description 1
- 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 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
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- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- PJKVFARRVXDXAD-UHFFFAOYSA-N 2-naphthaldehyde Chemical class C1=CC=CC2=CC(C=O)=CC=C21 PJKVFARRVXDXAD-UHFFFAOYSA-N 0.000 description 1
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- DDTHMESPCBONDT-UHFFFAOYSA-N 4-(4-oxocyclohexa-2,5-dien-1-ylidene)cyclohexa-2,5-dien-1-one Chemical compound C1=CC(=O)C=CC1=C1C=CC(=O)C=C1 DDTHMESPCBONDT-UHFFFAOYSA-N 0.000 description 1
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- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000037429 base substitution Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl 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
- 229910052790 beryllium Inorganic materials 0.000 description 1
- ATBAMAFKBVZNFJ-UHFFFAOYSA-N beryllium atom Chemical compound [Be] ATBAMAFKBVZNFJ-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- MMUFAGXJPKNAHT-UHFFFAOYSA-N copper;quinolin-8-ol Chemical compound [Cu].C1=CN=C2C(O)=CC=CC2=C1 MMUFAGXJPKNAHT-UHFFFAOYSA-N 0.000 description 1
- SIFHTIHFPPIGBL-UHFFFAOYSA-N ctk2i0750 Chemical class C12=C3C4=CC=CC3=CC=C2C=CC=C1C1=C4CC2=CC=CC=C21 SIFHTIHFPPIGBL-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
- RMBGFUOEZINVEP-UHFFFAOYSA-N cyclohexa-2,5-diene-1,4-dione;phenol Chemical compound OC1=CC=CC=C1.O=C1C=CC(=O)C=C1 RMBGFUOEZINVEP-UHFFFAOYSA-N 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
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([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
- 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
- 238000003618 dip coating Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 210000003746 feather Anatomy 0.000 description 1
- 244000144992 flock Species 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 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
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005241 heteroarylamino group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002460 imidazoles Chemical class 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
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910000765 intermetallic Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 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
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 150000002545 isoxazoles Chemical class 0.000 description 1
- 239000011133 lead 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
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- VQOXIYILDDQNTQ-UHFFFAOYSA-N manganese quinolin-8-ol Chemical group [Mn].Oc1cccc2cccnc12 VQOXIYILDDQNTQ-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([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
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- IKXKTLBKRBLWNN-UHFFFAOYSA-N pentacene Chemical class C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21.C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 IKXKTLBKRBLWNN-UHFFFAOYSA-N 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 150000004032 porphyrins Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003220 pyrenes Chemical class 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical compound N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 description 1
- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical compound C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- GNHGQOQUCKGFCV-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1 GNHGQOQUCKGFCV-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000013519 translation Methods 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
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 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
- 230000000007 visual effect Effects 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 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
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- 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
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- 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
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
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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]
- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection layers
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
- H10K85/6565—Oxadiazole compounds
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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- 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
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- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The present invention provides a kind of new heterocyclic compound and utilizes its organic illuminating element.
Description
Technical field
The present invention relates to a kind of new heterocyclic compound and include its organic illuminating element.
Background technology
Generally, organic light emission phenomenon refers to the phenomenon that luminous energy is converted electrical energy into by using organic material.Using organic
The organic illuminating element visual angle of luminescence phenomenon is wide, contrast is excellent, the response time is fast, and brightness, driving voltage and response speed
Excellent performance is spent, therefore substantial amounts of research has been carried out to organic illuminating element.
Organic illuminating element, which typically has, includes anode, negative electrode and the structure for being placed in organic material layer therebetween.It is described to have
Machine material layer has the sandwich construction being made up of respectively different materials, to improve the efficiency of organic illuminating element and stability, example
Such as, hole injection layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer etc. can be included.In this organic light emission
In the structure of element, if applying voltage between two electrodes, hole is from anode injection organic material layer and electronics from the moon
Pole injection organic material layer, exciton can be formed when injected holes and electrode meet, and can be sent out when exciton returns ground state
Light.
For the organic material as described above for organic illuminating element, it is necessary to persistently develop new material.
Citation
Patent document 1：Korean Patent Publication No. 10-2000-0051826
The content of the invention
Technical problem
The present invention provides a kind of new heterocyclic compound and includes its organic illuminating element.
Technical scheme
The present invention provides a kind of compound represented by formula 1 below.
[chemical formula 1]
In the chemical formula 1,
X is O or S,
R1To R4In at least two be identical-L-Ar, remaining is hydrogen,
L is singly-bound；Substituted or unsubstituted C6-60Arlydene；It is or substituted or unsubstituted comprising in O, N, Si and S
The C of one or more atoms2-60Heteroarylidene,
Ar is substituted or unsubstituted C6-60Aryl；Or it is substituted or unsubstituted include O, N, Si and S in one or
The C of multiple atoms2-60Heteroaryl,
But Ar is not pyridine radicals.
In addition, the present invention provides a kind of organic illuminating element, the organic illuminating element includes：First electrode；With it is described
The relative second electrode of first electrode；And one or more layers organic material between the first electrode and the second electrode
The bed of material, one or more layers organic material layer includes the compound represented by the chemical formula 1 in the organic material layer.
Invention effect
The described compound represented by chemical formula 1 can be used as the material of the organic material layer of organic illuminating element, and
Efficiency and low driving voltage and/or life performance can be improved in organic illuminating element.Especially, it is described by chemical formula 1
The compound of expression can be used as hole injection, hole transport, hole injection and transmission, luminous, electric transmission or electron injection material
Material.
Brief description of the drawings
Fig. 1 shows the example of the organic illuminating element comprising substrate 1, anode 2, luminescent layer 3 and negative electrode 4.
Fig. 2 is shown comprising substrate 1, anode 2, hole injection layer 5, hole transmission layer 6, luminescent layer 7, the and of electron transfer layer 8
The example of the organic illuminating element of negative electrode 4.
Embodiment
In order to help to understand the present invention, it is described in more detail below.
The present invention provides the compound represented by the chemical formula 1.
In this manual,OrIntention is connected to the key of other substituents.
In this manual, term " substitution is unsubstituted " intention is by selected from deuterium；Halogen group；Itrile group；Nitro；Hydroxyl；
Carbonyl；Ester group；Imide；Amino；Phosphine epoxide；Alkoxy；Aryloxy group；Alkyl sulfide epoxide (alkylthioxy group)；Virtue
Base sulphur epoxide；Alkyl sulphonyl (alkylsulfoxy group)；Aryl sulfonyl；Silicyl (silyl group)；Boron
Base；Alkyl；Cycloalkyl；Alkenyl；Aryl；Aralkyl；Arylalkenyl；Alkylaryl；Alkyl amine group；Aralkyl amido；Heteroaryl amine
Base；Arylamine group；Aryl phosphino-；Or one or more of heterocyclic radical comprising one or more N, O and S atom substituent takes
In generation, is unsubstituted, or the connected substitution or unsubstituted of two or more substituents in the substituent illustrated in intention.For example,
" the connected substituent of two or more substituents " can be xenyl.In other words, it can be understood as xenyl can be virtue
The substituent that base or two phenyl are connected.
In this manual, the carbon number of carbonyl is not particularly limited, but carbon number is preferably 1 to 40.Specifically
For, the compound of following structure, but not limited to this can be included.
In this manual, for ester group, the oxygen of ester group can be by straight chain, side chain or loop chain that carbon number is 1 to 25
Alkyl or the aryl that carbon number is 6 to 25 substitute.Specifically, the compound of following structural formula can be included, but be not limited to
This.
In this manual, the carbon number of imide is not particularly limited, but carbon number is preferably 1 to 25.
Specifically, the compound of following structure, but not limited to this can be included.
In this manual, silicyl is specifically comprising trimethyl silyl, triethylsilyl, tert-butyl group diformazan
Base silicyl, vinyldimethylsilyl, propyl-dimethyl silicyl, triphenyl-silyl, diphenylmethyl silicon
Alkyl, phenyl silyl groups etc., but not limited to this.
In this manual, boryl is specifically comprising trimethyl boryl, triethyl group boryl, fert-butyidimethylsilyl boryl, triphen
Base boryl, phenyl boryl etc., but not limited to this.
In this manual, the example of halogen group includes fluorine, chlorine, bromine or iodine.
In this manual, the alkyl can be straight or branched, and carbon number is not particularly limited, but preferably
For 1 to 40.According to an embodiment, the carbon number of the alkyl is 1 to 20.According to another embodiment, the alkane
The carbon number of base is 1 to 10.According to further embodiment, the carbon number of the alkyl is 1 to 6.The specific reality of alkyl
Example includes methyl, ethyl, propyl group, n-propyl, isopropyl, butyl, normal-butyl, isobutyl group, the tert-butyl group, sec-butyl, 1- methyl-fourth
Base, 1- Ethyl-butyls, amyl group, n-pentyl, isopentyl, neopentyl, tertiary pentyl, hexyl, n-hexyl, 1- methyl amyls, 2- methyl
Amyl group, 4- methyl -2- amyl groups, 3,3- dimethylbutyls, 2- ethyl-butyls, heptyl, n-heptyl, 1- methylhexyls, cyclopenta first
Base, cyclohexyl methyl, octyl group, n-octyl, t-octyl, 1- methylheptyls, 2- ethylhexyls, 2- propylpentyls, n-nonyl, 2,2-
Methylheptyl, 1- Ethyl-propyls, 1,1- Dimethyl-propyls, isohesyl, 2- methyl amyls, 4- methylhexyls, 5- methylhexyls
Deng, but not limited to this.
In this manual, the alkenyl can be straight or branched, and carbon number is not particularly limited, but preferably
For 2 to 40.According to an embodiment, the carbon number of the alkenyl is 2 to 20.According to another embodiment, the alkene
The carbon number of base is 2 to 10.According to further embodiment, the carbon number of the alkenyl is 2 to 6.Instantiation includes
Vinyl, 1- acrylic, isopropenyl, 1- cyclobutenyls, 2- cyclobutenyls, 3- cyclobutenyls, 1- pentenyls, 2- pentenyls, 3- amylenes
Base, 3-methyl-1-butene base, 1,3- butadienyls, pi-allyl, 1- phenyl vinyl -1- bases, 2- phenyl vinyl -1- bases, 2,
Double (diphenyl -1- bases) ethene of 2- diphenylacetylene -1- bases, 2- phenyl -2- (naphthyl -1- bases) vinyl -1- bases, 2,2-
Base -1- bases, stilbene radicals (stilbenyl group), styryl etc., but not limited to this.
In this manual, cycloalkyl is not particularly limited, but carbon number is preferably 3 to 60.According to an implementation
Scheme, the carbon number of the cycloalkyl is 3 to 30.According to another embodiment, the carbon number of the cycloalkyl for 3 to
20.According to further embodiment, the carbon number of the cycloalkyl is 3 to 6.Specifically comprising cyclopropyl, cyclobutyl, ring penta
Base, 3- methylcyclopentyls, 2,3- dimethylcyclopentyls, cyclohexyl, 3- methylcyclohexyls, 4- methylcyclohexyls, 2,3- methyl rings
Hexyl, 3,4,5- trimethylcyclohexyls, 4- tert-butylcyclohexyls, suberyl, cyclooctyl etc., but not limited to this.
In this manual, aryl is not particularly limited, but carbon number is preferably 6 to 60, can be monocyclic aryl
Or polyaromatic.According to an embodiment, the carbon number of the aryl is 6 to 30.It is described according to another embodiment
The carbon number of aryl is 6 to 20.The monocyclic aryl can include phenyl, xenyl, terphenyl etc., but not limited to this.Institute
State polyaromatic can include naphthyl, anthryl, phenanthryl, pyrenyl, base,Base (crycenyl), fluorenyl etc., but not limited to this.
In this manual, fluorenyl can be substituted, and two substituents can bond together and form spirane structure.Work as institute
State fluorenyl it is substituted when, can include
Deng, but not limited to this.
In this manual, heterocyclic radical is as heteroatomic heterocyclic radical, to carbon original comprising one or more O, N, Si and S
Subnumber is not particularly limited, but carbon number is preferably 2 to 60.The example of heterocyclic radical include thienyl, furyl, pyrrole radicals,
Imidazole radicals, thiazolyl, oxazolyl, oxadiazolyls, triazolyl, pyridine radicals, bipyridyl, pyrimidine radicals, triazine radical, triazolyl, a word used for translation
Piperidinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolyl, quinoxalinyl, phthalazinyl, Pyridopyrimidine base, pyrido-pyrazine base,
Pyrazine and pyrazinyl, isoquinolyl, indyl, carbazyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzo carbazole
Base, benzothienyl, dibenzothiophenes base, benzofuranyl, phenanthroline (phenanthroline), thiazolyl, isoxazoles
Ji, oxadiazolyls, thiadiazolyl group, benzothiazolyl, phenothiazinyl, dibenzofuran group etc., but not limited to this.
In this manual, the aryl in aralkyl, arylalkenyl, alkylaryl, arylamine group and foregoing Examples of aryl groups
It is identical.In this manual, alkyl is identical with foregoing examples of alkyl in aralkyl, alkylaryl, alkyl amine group.In this explanation
In book, the foregoing description to heterocyclic radical is applicable to the heteroaryl in heteroaryl amido.In this manual, alkenyl in arylalkenyl
It is identical with foregoing alkenyl example.In this manual, the foregoing description to aryl is applicable to arlydene, and divalent group
Except.In this manual, the foregoing description to heterocyclic radical is applicable to heteroarylidene, and except divalent group.At this
In specification, the foregoing description to aryl or cycloalkyl is applicable to hydrocarbon ring, non-univalent perssad and two substituents bondings and shape
Except.In this manual, the foregoing description to heterocyclic radical is applicable to heterocycle, non-univalent perssad and two substituent keys
Close and formed except.
Preferably, R1To R4In two be identical-L-Ar, remaining is hydrogen.That is, the compound represented by the chemical formula 1
It can be represented by any one chemical formula in formula 1 below -1 to 1-6.
[chemical formula 1-1]
[chemical formula 1-2]
[chemical formula 1-3]
[chemical formula 1-4]
[chemical formula 1-5]
[chemical formula 1-6]
Preferably, L is singly-bound or any one selected from following group,
It is highly preferred that L is 1,3- phenylenes, Isosorbide-5-Nitrae-phenylene or biphenyl -4,4 '-diyl (biphenyl-4,4 ' -
diyl)。
Preferably, Ar is any one selected from following group,
In the chemical formula,
X1、X2And X3It is separately CH or N,
X4And X5It is separately S, O or NH,
X6And X7It is separately CH or N,
X8To X10In it is at least one be N, remaining is CH,
R1To R7It is separately hydrogen, C6-60Aryl or the C for including one or more of O, N, Si and S atom2-60
Heteroaryl.
Hereinbefore, X is worked as1To X7For NH or CH when, can be connected instead of NH or CH HOr substituted R1To R4。
Preferably, R1To R7It is separately hydrogen, phenyl, xenyl, naphthyl or pyridine radicals.
It is highly preferred that Ar is any one selected from following group,
Preferably, the compound represented by the chemical formula 1 is any compound selected from following group,
The compound represented by the chemical formula 1 can be prepared by the preparation method of such as formulas below 1.For described
Preparation method, more specifically described in preparation example described later.
[reaction equation 1]
In the reaction equation 1,
X、R1、R2、R3、R4, L and Ar definition it is same as mentioned above,
R′1To R '4In at least two be 4,4,5,5- tetramethyl -1,3,2- dioxaborolanes bases (4,4,5,5-
Tetramethyl-1,3,2-dioxaborolanyl) and remaining is hydrogen, and X ' is halogen, or R '1To R '4In at least two be
Halogen and remaining be hydrogen, X ' is 4,4,5,5- tetramethyls -1,3,2- dioxaborolanes base (4,4,5,5-tetramethyl-
1,3,2-dioxaborolanyl)。
The reaction is preferably carried out in the presence of potassium carbonate.In addition, the reaction is preferably in tetra-triphenylphosphine palladium
(tetrakistriphenyl-phosphinopalladium) carried out under catalyst.Carried out 1 hour moreover, the reaction is preferred
To 10 hours, reaction can also be cleaned and/or dried as needed after terminating.
In addition, the present invention provides a kind of organic illuminating element for including the compound represented by the chemical formula 1.As one
Individual example, the present invention provide a kind of organic illuminating element, and it is included：First electrode；Second electricity relative with the first electrode
Pole；And one or more layers organic material layer between the first electrode and the second electrode, the organic material layer
In one or more layers include the compound that is represented by the chemical formula 1.
The organic material layer of the organic illuminating element of the present invention can be that single layer structure or two layers or multilayer are organic
The sandwich construction of material layer.Noted for example, the organic illuminating element of the present invention can have as organic material layer comprising hole
Enter the structure of layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer etc., but the structure of organic illuminating element is unlimited
In this, less organic layer can be included.
In addition, the organic material layer can include hole injection layer, hole transmission layer or carry out hole injection and biography simultaneously
Defeated layer, the hole injection layer, hole transmission layer or carries out the layer of hole injection and transmission and includes by the chemical formula simultaneously
1 compound represented.
In addition, the organic material layer can include luminescent layer, the luminescent layer includes the chemical combination represented by the chemical formula 1
Thing.
In addition, the organic material layer can include electron transfer layer or electron injecting layer, the electron transfer layer or electricity
Sub- implanted layer includes the compound represented by the chemical formula 1.
In addition, the electron transfer layer, electron injecting layer or carry out simultaneously electron injection and electric transmission layer include by
The compound that the chemical formula 1 represents.Especially, have excellent heat steady according to the compound represented by chemical formula 1 of the present invention
HOMO energy levels, high triplet energies (ET) and the hole stability qualitative, more than 6.0eV is deep.Moreover, will be by the chemistry
The compound that formula 1 represents is used to carry out the organic material layer of electron injection and electric transmission simultaneously when, this can be used in mixed way
N-type dopant used in industry.
In addition, the organic material layer can include luminescent layer and electron transfer layer, the electron transfer layer is included by described
The compound that chemical formula 1 represents.
In addition, the organic illuminating element of the present invention can have anode, one or more layers organic material layer and negative electrode
The organic illuminating element for the structure (normal type) being sequentially laminated on substrate.Moreover, the organic illuminating element of the present invention can
To be that there is negative electrode, one or more layers organic material layer and anode to be sequentially laminated the reverse geometry (inverted on substrate
Type organic illuminating element).For example, the structure of the organic illuminating element of one embodiment of the invention is shown in Fig. 1 and Fig. 2.
Fig. 1 be comprising substrate 1, anode 2, luminescent layer 3, negative electrode 4 organic illuminating element schematic diagram.In such structure
In, the compound represented by the chemical formula 1 can be included in the luminescent layer.
Fig. 2 is to include substrate 1, anode 2, hole injection layer 5, hole transmission layer 6, luminescent layer 7, electron transfer layer 8 and the moon
The schematic diagram of the organic illuminating element of pole 4.In such a configuration, the compound represented by the chemical formula 1 can be included in institute
State in one or more layers in hole injection layer, hole transmission layer, luminescent layer and electron transfer layer.
The organic illuminating element of the present invention is included by the chemical formula 1 except one or more layers in the organic material layer
Outside the compound of expression, it can be manufactured using material as known in the art and method.Moreover, the organic illuminating element
During comprising multiple organic material layers, the organic material layer can be formed with identical or different material.
For example, the organic illuminating element of the present invention can be by by first electrode, organic material layer and second electrode successively layer
It is pressed on substrate to manufacture.Now, sputtering method (sputtering) or e-beam evaporation (e-beam are utilized
) etc. evaporation physical vaporous deposition (physical Vapor Deposition PVD) on substrate deposited metal or
Conductive metal oxide or their alloy, to form anode, formed on anode comprising hole injection layer, hole
After the organic material layer of transport layer, luminescent layer and electron transfer layer, deposition can be as the material of negative electrode on organic material layer.
In addition to such method, it can also be made by being sequentially depositing on substrate cathode material, organic material layer, anode material
Into organic illuminating element.
In addition, when manufacturing organic illuminating element, not only solution coating process can also be passed through by vacuum deposition method
The compound represented by the chemical formula 1 is formed as into organic material layer.The solution coating process refer to spin coating, dip-coating, blade coating,
Ink jet printing, silk-screen printing, spraying, roller coat etc., but not limited to this.
, can by being sequentially depositing cathode material, organic material layer, anode material on substrate in addition to described method
To manufacture organic illuminating element (WO 2003/012890).But manufacture method not limited to this.
In an example, the first electrode is anode, and the second electrode is negative electrode, or the first electrode is
Negative electrode, the second electrode are anode.
The anode material is generally preferably using the big material of work function, so that hole being capable of successfully injection organic material
Layer.The instantiation of the anode material includes metal or their alloys such as vanadium, chromium, copper, zinc, gold；Zinc oxide, indium oxide,
The metal oxides such as tin indium oxide (ITO), indium zinc oxide (IZO)；ZnO:Al or SNO2:The combination of the metals such as Sb and oxide
Thing；The conduction such as poly- (3 methyl thiophene), poly- [3,4- (epoxides of ethylidene -1,2- two) thiophene] (PEDOT), polypyrrole and polyaniline
Property polymer, but not limited to this.
The cathode material is generally preferably using the small material of work function, so that electronics is easy to injection organic material layer.Institute
State cathode material instantiation include the metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminium, silver, tin and lead or they
Alloy；LiF/Al or LiO2Sandwich such as/Al etc., but not limited to this.
The hole injection layer is preferably used with following ability from the layer in electrode injection hole, hole-injecting material
Compound：Can transporting holes, so as to the hole of anode injection effect and to luminescent layer or luminescent material with excellent
Different hole injection effect, and prevent that caused exciton moves to electron injecting layer or electron injection material in luminescent layer, also has
There is excellent film Forming ability.The HOMO (highest occupied molecular orbital(HOMO)) of hole-injecting material is preferably between the work(of anode material
Between the HOMO of function and surrounding organic material layer.The instantiation of hole-injecting material include metalloporphyrin (porphyrin),
Oligopoly thiophene, arylamine class organic material, the azepine Benzophenanthrene organic material of six nitrile six, quinacridone (quinacridone) class have
Machine material, (perylene) class organic material, anthraquinone and polyaniline and polythiophene class electric conductive polymer etc., but be not limited to
This.
The hole transmission layer is to receive hole and by the layer of hole transport to luminescent layer from hole injection layer, as hole
Transmission material is adapted to use following material：Hole can be received from anode or hole injection layer and be transferred to luminescent layer, and to sky
Cave has high mobility.Instantiation includes arylamine class organic material, electric conductive polymer and conjugate moiety and non-simultaneously be present
Block copolymer of conjugate moiety etc., but not limited to this.
The luminescent material be can receive hole respectively from hole transmission layer and electron transfer layer and electronics make its with reference to and
The material of the light of visible region is sent, the luminescent material, which preferably uses, has favourable quantum efficiency to fluorescence or phosphorescence
Material.Instantiation includes 8-hydroxyquinoline aluminium complex (Alq3)；Carbazole compound；Two polystyrene (dimerized
Styryl) compound；BAlq；10- hydroxy benzos quinoline-metallic compound；Benzoxazole, benzothiazole and benzimidazole
Compound；Poly- compound of being birdsed of the same feather flock together (to phenylene vinylidene)；Loop coil (spiro) compound；Polyfluorene, lycid alkene etc., but not limited to this.
The luminescent layer can include material of main part and dopant material.Material of main part includes fused aromatic rings derivative or containing miscellaneous
Cycle compound etc..Specifically, fused aromatic rings derivative includes anthracene derivant, pyrene derivatives, naphthalene derivatives, pentacene
(pentacene) derivative, phenanthrene compound, fluoranthene compound etc., nitrogen-containing heterocgcies include carbazole derivates, dibenzofurans
Derivative, ladder type (ladder-type) furan compound, pyrimidine derivatives etc., but not limited to this.
Dopant material includes aromatic amine derivative, styrylamine compound, boron complex, fluoranthene compound, metal network
Compound etc..Specifically, aromatic amine derivative is fused aromatic rings derivative and bag with substituted or unsubstituted arylamino
Containing the pyrene with arylamino, anthracene,Two indeno pyrenes (peryflanthene) etc., styrylamine compound is for substitution or not
Substitution has the compound of at least one aryl vinyl on substituted arylamine, and is selected from aryl, silicyl, alkyl, ring
One or more substituent in alkyl and arylamino is substituted or unsubstituted.Specifically, styrylamine compound
Comprising styrylamine, styrene diamines, styrene triamine, styrene tetramine etc., but not limited to this.In addition, metal complex bag
Containing iridium complex, platinum complex etc., but not limited to this.It can be used by following chemistry preferably as the dopant material
The compound that formula 2 represents.
[chemical formula 2]
In the chemical formula 2,
R8To R15It is separately hydrogen, halogen, substituted or unsubstituted C1-20Alkyl, substituted or unsubstituted C3-10Ring
Alkyl, substituted or unsubstituted C3-30AIkylsilyl groups, substituted or unsubstituted C8-30Arylsilyl groups, substitution do not take
The C in generation1-20Alkoxy, substituted or unsubstituted C6-20Aralkyl or substituted or unsubstituted C6-10Aryl,
Ar1To Ar4It is separately substituted or unsubstituted C6-30Aryl, but the Ar1To Ar4In at least one difference
Independently by C1-20Alkyl, cyano group, halogen, nitro or carbonyl substitution.
Preferably, R8To R15Middle R9And R13It is separately substituted or unsubstituted C1-20Alkyl, remaining is hydrogen.It is more excellent
Selection of land, R8To R15Middle R9And R13For isopropyl, remaining is hydrogen.
Preferably, Ar1To Ar4For by C1-20Alkyl or the phenyl of cyano group substitution.It is highly preferred that Ar1And Ar3For by C1-20Alkane
The phenyl of base substitution, Ar2And Ar4For the phenyl substituted by cyano group.
The representative example of the compound represented by the chemical formula 2 is as follows：
The electron transfer layer is to receive electronics and by the layer of electric transmission to luminescent layer from electron injecting layer, as electronics
Transmission material is adapted to use following material：Electronics can be received from negative electrode and be transferred to luminescent layer, and there is high migrate to electronics
Rate.Instantiation includes 8-hydroxyquinoline aluminium complex；Containing Alq3Complex compound；Organic free radical compound；Flavonol-metal
Complex compound etc., but not limited to this.As used in the prior art, electron transfer layer can be together with required arbitrary cathode material
Use.Specifically, the example of suitable cathode material is that work function is small and conventional material with aluminium lamination or silver layer.It is specific and
Speech, cathode material includes caesium, barium, calcium, ytterbium and samarium, in each case with aluminium lamination or silver layer.
The electron injecting layer is preferably used with following ability from the layer of electrode injection electronics, electron injection material
Compound：Electronics can be transmitted, so as to the electronic injection effect from negative electrode and to luminescent layer or luminescent material
With excellent electron injection effect, and prevent that caused exciton is migrated to hole injection layer, also with excellent in luminescent layer
Film Forming ability.Specifically, electron injection material includes Fluorenone (fluorenone), anthraquinone and bismethane
(anthraquinodimethane), phenoquinone (diphenoquinone), thiopyrandioxide, oxazole, oxadiazoles,
Triazole, imidazoles, tetrabasic carboxylic acid, fluorenylidene-methane, anthrone etc. and its derivative, metal complex and nitrogenous 5 membered ring derivatives etc.,
But not limited to this.
The metal complex includes 8-hydroxyquinoline lithium, double (8-hydroxyquinoline) zinc, double (8-hydroxyquinoline) copper, double
It is (8-hydroxyquinoline) manganese, three (8-hydroxyquinoline) aluminium, three (2- methyl -8-hydroxyquinoline) aluminium, three (8-hydroxyquinoline) galliums, double
(10- hydroxy benzos [h] quinoline) beryllium, double (10- hydroxy benzos [h] quinoline) zinc, double (2- methyl -8- quinoline) chloro galliums, double (2-
Methyl -8- quinoline) (orthoresol) gallium, double (2- methyl -8- quinoline) (1- naphthols) aluminium, double (2- methyl -8- quinoline) (beta naphthals)
Gallium etc., but not limited to this.
Organic illuminating element material used in of the present invention can be top emission type, bottom emission type, two-sided
Light emitting-type.
In addition, for the compound represented by the chemical formula 1, in addition to organic illuminating element, it has been further included in
Machine solar cell or organic transistor.
The compound that is represented by the chemical formula 1 and the organic light emission member for including it are will be described in the following embodiments
The preparation of part.However, following embodiments are only intended to the example present invention, the scope of the present invention is not limited to following embodiments.
Embodiment 1 (E1)
By the compound (10.0g, 23.8mmol) represented by the chemical formula A and the chemical combination represented by the chemical formula B
After thing (12.7g, 47.6mmol) is dissolved completely in THF (100mL), add in 50mL water dissolved with potassium carbonate (9.9g,
Solution 71.4mmol).After adding tetra-triphenylphosphine palladium (825mg, 0.71mmol), heating stirring 8 hours.Cool the temperature to
After normal temperature terminates reaction, filter out solution of potassium carbonate and obtain white solid.The white solid THF and ethyl acetate that will be filtrated to get
It is respectively washed the compound (13.4g, yield 89%) for, being prepared for being represented twice by the chemical formula E1.
MS[M+H]+=631
Embodiment 2 (E2)
In addition to each initial feed is identical with the reaction equation, it is prepared for by method same as Example 1 by institute
State the compound of chemical formula E2 expressions.
MS[M+H]+=783
Embodiment 3 (E3)
In addition to each initial feed is identical with the reaction equation, it is prepared for by method same as Example 1 by institute
State the compound of chemical formula E3 expressions.
MS[M+H]+=783
Embodiment 4 (E4)
In addition to each initial feed is identical with the reaction equation, it is prepared for by method same as Example 1 by institute
State the compound of chemical formula E4 expressions.
MS[M+H]+=721
Embodiment 5 (E5)
In addition to each initial feed is identical with the reaction equation, it is prepared for by method same as Example 1 by institute
State the compound of chemical formula E5 expressions.
MS[M+H]+=781
Embodiment 6 (E6)
In addition to each initial feed is identical with the reaction equation, it is prepared for by method same as Example 1 by institute
State the compound of chemical formula E6 expressions.
MS[M+H]+=799
Embodiment 7 (E7)
In addition to each initial feed is identical with the reaction equation, it is prepared for by method same as Example 1 by institute
State the compound of chemical formula E7 expressions.
MS[M+H]+=729
Embodiment 8 (E8)
In addition to each initial feed is identical with the reaction equation, it is prepared for by method same as Example 1 by institute
State the compound of chemical formula E8 expressions.
MS[M+H]+=783
Embodiment 9 (E9)
In addition to each initial feed is identical with the reaction equation, it is prepared for by method same as Example 1 by institute
State the compound of chemical formula E9 expressions.
MS[M+H]+=781
Embodiment 10 (E10)
In addition to each initial feed is identical with the reaction equation, it is prepared for by method same as Example 1 by institute
State the compound of chemical formula E10 expressions.
MS[M+H]+=539
Embodiment 11 (E11)
In addition to each initial feed is identical with the reaction equation, it is prepared for by method same as Example 1 by institute
State the compound of chemical formula E11 expressions.
MS[M+H]+=693
Embodiment 12 (E12)
In addition to each initial feed is identical with the reaction equation, it is prepared for by method same as Example 1 by institute
State the compound of chemical formula E12 expressions.
MS[M+H]+=693
Embodiment 13 (E13)
In addition to each initial feed is identical with the reaction equation, it is prepared for by method same as Example 1 by institute
State the compound of chemical formula E13 expressions.
MS[M+H]+=625
Experimental example 1
Being coated with thickness isThe glass substrate of ITO (tin indium oxide) film be placed in dissolved with cleaning agent
It is cleaned by ultrasonic in distilled water.Now, the product of Fischer companies has been used as cleaning agent, has been used as distilled water
The distilled water filtered twice by the filter (Filter) produced by Millipore companies.ITO is cleaned 30 minutes
Afterwards, ultrasonic cleaning is repeated twice with distilled water, cleaned 10 minutes.After having been cleaned with distilled water, then with isopropanol, acetone, methanol
Solvent is cleaned by ultrasonic and dried, and is then transferred to plasma cleaner.The substrate is cleaned using oxygen plasma 5 minutes
Afterwards, then by substrate it is transferred to vacuum deposition apparatus.
On the ito transparent electrode so prepared, deposit HI-A compounds by thermal vacuum is to form thickness
Hole injection layer.On the hole injection layer, pass through the following HAT compounds of vacuum moulding machine successivelyAnd following HT-
A compoundsForm hole transmission layer.
Then, on the hole transport layer, by with 25:1 weight BH compounds more following than vacuum moulding machine and BDization
Compound is to form film thicknessLuminescent layer.
On the light-emitting layer, by with 1:Compound E1 of 1 weight than vacuum moulding machine embodiment 1 and following LiQ chemical combination
Thing is to form thicknessElectron injection and transport layer.In the electron injection and transport layer, by being sequentially depositing
Thickness isLithium fluoride (LiF) and thickness beAluminium form negative electrode.
During described, the sedimentation rate of organic material is keptExtremelyNegative electrode
Lithium fluoride sedimentation rate is keptAl deposition speed is keptAnd deposit when vacuum keep 1 ×
10-7To 5 × 10-5Torr, organic illuminating element is thus manufactured.
Experimental example 2 to 13
Except replace embodiment 1 compound E1 using embodiment 2 to 13 compound E2 to E13 in addition to, by with institute
State the identical method of experimental example 1 and manufacture organic illuminating element.
Contrast experiment's example 1 to 12
Except replace embodiment 1 compound E1 use following compound ET-A to ET-L in addition to, by with the experiment
The identical method of example 1 has manufactured organic illuminating element.
To the organic illuminating element that is manufactured in the experimental example and contrast experiment's example in 10mA/cm2Current density under survey
Determine driving voltage and luminous efficiency, and in 20mA/cm2Current density under determine and reach 90% relative to original intensity
Time (T90), the results are shown in table 1 below and table 2.
【Table 1】
【Table 2】
From upper table 1 it has been confirmed that the compound represented by chemical formula 1 of the present invention can be used for the energy of organic illuminating element
Enough organic material layers for carrying out electron injection and electric transmission simultaneously.
In addition, contrast experiment's example 1,2,3 and 6 of the experimental example of upper table 1 and upper table 2 is contrasted it has been confirmed that such as this
The chemical formula 1 of invention substitutes the compound for having two substituents of identical to have with substitution on dibenzofurans or dibenzothiophenes
The compound phase ratio of different substituents, it is obvious excellent in terms of the driving voltage of organic illuminating element, efficiency and life-span.
In addition, contrast experiment's example 5 of the experimental example of upper table 1 and upper table 2 is contrasted it has been confirmed that with being passed with electronics
The situation of the bad substituent of Movement Capabilities such as pyridine is compared, and the performance of organic illuminating element is improved.
In addition, contrast experiment's example 4,7 to 12 of the experimental example of upper table 1 and upper table 2 is contrasted it has been confirmed that such as this hair
Bright chemical formula 1 in dibenzofurans and dibenzothiophenes skeleton on the phenyl of side substitution have the compound of identical substituent with
Substitution has the compound phase ratio of identical substituent, driving voltage, efficiency and the life-span aspect of organic illuminating element on different phenyl
It is obvious excellent.
Symbol description
1：Substrate 2：Anode
3：Luminescent layer 4：Negative electrode
5：Hole injection layer 6：Hole transmission layer
7：Luminescent layer 8：Electron transfer layer
Claims (10)
- A kind of 1. compound represented by formula 1 below：[chemical formula 1]In the chemical formula 1,X is O or S,R1To R4In at least two be identical-L-Ar, remaining is hydrogen,L is singly-bound；Substituted or unsubstituted C6-60Arlydene；Or it is substituted or unsubstituted include O, N, Si and S in one or The C of multiple atoms2-60Heteroarylidene,Ar is substituted or unsubstituted C6-60Aryl；Or substituted or unsubstituted include one or more of O, N, Si and S original The C of son2-60Heteroaryl,But Ar is not pyridine radicals.
- 2. compound according to claim 1, wherein,R1To R4In two be identical-L-Ar, remaining is hydrogen.
- 3. compound according to claim 1, wherein,L is singly-bound or any one selected from following group,
- 4. compound according to claim 1, wherein,L is 1,3- phenylenes, 1,4- phenylenes or biphenyl -4,4 '-diyl.
- 5. compound according to claim 1, wherein,Ar is any one selected from following group,In the chemical formula,X1、X2And X3It is separately CH or N,X4And X5It is separately S, O or NH,X6And X7It is separately CH or N,X8To X10In it is at least one be N, remaining is CH,R1To R7It is separately hydrogen, C6-60Aryl or the C for including one or more of O, N, Si and S atom2-60Heteroaryl Base.
- 6. compound according to claim 1, wherein,Ar is any one selected from following group,
- 7. compound according to claim 1, wherein,The compound represented by the chemical formula 1 is any compound selected from following group,
- 8. a kind of organic illuminating element, it is included：First electrode；The second electrode relative with the first electrode；And institute State one or more layers organic material layer between first electrode and the second electrode, one layer or more in the organic material layer Layer includes the compound any one of claim 1 to 7.
- 9. organic illuminating element according to claim 8, wherein,Organic material layer comprising the compound is electron injecting layer；Electron transfer layer；Or electron injection and electricity are carried out simultaneously The layer of son transmission.
- 10. organic illuminating element according to claim 8, wherein,The organic illuminating element includes luminescent layer, and the luminescent layer includes the change represented by formula 2 below as dopant Compound,[chemical formula 2]In the chemical formula 2,R8To R15It is separately hydrogen, halogen, substituted or unsubstitutedC1-20Alkyl, substituted or unsubstituted C3-10Cycloalkyl, Substituted or unsubstituted C3-30AIkylsilyl groups, substituted or unsubstituted C8-30It is arylsilyl groups, substituted or unsubstituted C1-20Alkoxy, substituted or unsubstituted C6-20Aralkyl or substituted or unsubstituted C6-10Aryl,Ar1To Ar4It is separately substituted or unsubstituted C6-30Aryl, but the Ar1To Ar4In it is at least one independently Ground is by C1-20Alkyl, cyano group, halogen, nitro or carbonyl substitution.
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| KR102095001B1 (en) | 2020-03-30 |
| CN107840835B (en) | 2021-08-31 |
| KR20180031224A (en) | 2018-03-28 |
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