CN109415375A - Heterocyclic compound and organic illuminating element comprising it - Google Patents
Heterocyclic compound and organic illuminating element comprising it Download PDFInfo
- Publication number
- CN109415375A CN109415375A CN201780041153.2A CN201780041153A CN109415375A CN 109415375 A CN109415375 A CN 109415375A CN 201780041153 A CN201780041153 A CN 201780041153A CN 109415375 A CN109415375 A CN 109415375A
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- Prior art keywords
- substituted
- unsubstituted
- aryl
- different
- same
- Prior art date
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- 150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 35
- 239000000126 substance Substances 0.000 claims abstract description 88
- 125000003118 aryl group Chemical group 0.000 claims description 137
- -1 nitro, hydroxyl Chemical group 0.000 claims description 121
- 229910052799 carbon Inorganic materials 0.000 claims description 118
- 229910052739 hydrogen Inorganic materials 0.000 claims description 63
- 239000001257 hydrogen Substances 0.000 claims description 63
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- 125000000623 heterocyclic group Chemical group 0.000 claims description 52
- 239000005416 organic matter Substances 0.000 claims description 50
- 150000002431 hydrogen Chemical class 0.000 claims description 49
- 238000006467 substitution reaction Methods 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 42
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 38
- 229910052805 deuterium Inorganic materials 0.000 claims description 38
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 238000002347 injection Methods 0.000 claims description 27
- 239000007924 injection Substances 0.000 claims description 27
- 125000005843 halogen group Chemical group 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 125000005264 aryl amine group Chemical group 0.000 claims description 21
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 19
- 230000005540 biological transmission Effects 0.000 claims description 18
- 125000000707 boryl group Chemical group B* 0.000 claims description 18
- 125000003282 alkyl amino group Chemical group 0.000 claims description 17
- 125000003368 amide group Chemical group 0.000 claims description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000005360 alkyl sulfoxide group Chemical group 0.000 claims description 10
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 10
- 125000004647 alkyl sulfenyl group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- 230000008859 change Effects 0.000 claims description 4
- 230000005611 electricity Effects 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims 2
- 125000003375 sulfoxide group Chemical group 0.000 claims 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- 229910052796 boron Inorganic materials 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 239000010410 layer Substances 0.000 description 192
- 150000001721 carbon Chemical group 0.000 description 109
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 58
- 230000015572 biosynthetic process Effects 0.000 description 54
- 238000003786 synthesis reaction Methods 0.000 description 54
- 238000000034 method Methods 0.000 description 31
- 229940125904 compound 1 Drugs 0.000 description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 28
- 239000000463 material Substances 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 22
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 16
- 230000000052 comparative effect Effects 0.000 description 14
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 14
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 125000001544 thienyl group Chemical group 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 13
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 13
- HJCUTNIGJHJGCF-UHFFFAOYSA-N 9,10-dihydroacridine Chemical class C1=CC=C2CC3=CC=CC=C3NC2=C1 HJCUTNIGJHJGCF-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 10
- 150000002790 naphthalenes Chemical class 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 9
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 239000004411 aluminium Substances 0.000 description 8
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 8
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 8
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 8
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 8
- 239000002019 doping agent Substances 0.000 description 8
- 125000002541 furyl group Chemical group 0.000 description 8
- 125000005561 phenanthryl group Chemical group 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- MYKQKWIPLZEVOW-UHFFFAOYSA-N 11h-benzo[a]carbazole Chemical compound C1=CC2=CC=CC=C2C2=C1C1=CC=CC=C1N2 MYKQKWIPLZEVOW-UHFFFAOYSA-N 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 7
- 239000004305 biphenyl Substances 0.000 description 7
- 235000010290 biphenyl Nutrition 0.000 description 7
- 125000004076 pyridyl group Chemical group 0.000 description 7
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 125000005580 triphenylene group Chemical group 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 125000004653 anthracenylene group Chemical group 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 6
- 125000004957 naphthylene group Chemical group 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 125000005562 phenanthrylene group Chemical group 0.000 description 6
- 125000005493 quinolyl group Chemical group 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 150000003643 triphenylenes Chemical group 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 229940125773 compound 10 Drugs 0.000 description 5
- 238000004770 highest occupied molecular orbital Methods 0.000 description 5
- 125000005956 isoquinolyl group Chemical group 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 229940126214 compound 3 Drugs 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 150000002220 fluorenes Chemical class 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 125000005241 heteroarylamino group Chemical group 0.000 description 4
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 4
- 229960005544 indolocarbazole Drugs 0.000 description 4
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 230000004888 barrier function Effects 0.000 description 3
- 150000001616 biphenylenes Chemical group 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000004696 coordination complex Chemical class 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 229910052733 gallium Inorganic materials 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 3
- 238000005240 physical vapour deposition Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 125000003373 pyrazinyl group Chemical group 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- 125000005017 substituted alkenyl group Chemical group 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- 239000005725 8-Hydroxyquinoline Substances 0.000 description 2
- 150000004325 8-hydroxyquinolines Chemical class 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 206010011224 Cough Diseases 0.000 description 2
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-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
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-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
- 239000002253 acid Substances 0.000 description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 125000005018 aryl alkenyl group Chemical group 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 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 2
- 150000004826 dibenzofurans Chemical class 0.000 description 2
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- MRNHPUHPBOKKQT-UHFFFAOYSA-N indium;tin;hydrate Chemical compound O.[In].[Sn] MRNHPUHPBOKKQT-UHFFFAOYSA-N 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 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
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 229960003540 oxyquinoline Drugs 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
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 150000003248 quinolines Chemical class 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 238000004544 sputter deposition Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
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- 150000003230 pyrimidines Chemical class 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 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
- 229910052711 selenium Inorganic materials 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([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
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 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
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 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
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 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
- 150000003852 triazoles Chemical class 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
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 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
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/20—Polycyclic condensed hydrocarbons
- C07C15/27—Polycyclic condensed hydrocarbons containing three rings
- C07C15/28—Anthracenes
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
- C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K50/15—Hole transporting layers
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- H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
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Abstract
This specification is related to the heterocyclic compound of chemical formula 1 and the organic illuminating element comprising it.
Description
Technical field
The South Korea patent application 10-2016- that this application claims submitted on 07 01st, 2016 to Koran Office
No. 0083734 priority, its contents are contained in this manual.
This specification is related to heterocyclic compound and the organic illuminating element comprising it.
Background technique
Organic light emission phenomenon is one of the example that electric current is converted into visible light by the internal procedure of specific organic molecule.
The principle of organic light emission phenomenon is as follows.When configuring organic matter layer between the anode and the cathode, if applying electricity between electrodes
Pressure, then electrons and holes can be injected into organic matter layer from cathode and anode respectively.It is injected into the electrons and holes of organic matter layer again
In conjunction with and form exciton (exciton), which transits to ground state again and issues light.Utilize the organic light emission member of this principle
Part can generally be constituted by cathode and anode and positioned at the organic matter layer between them, and the organic matter layer is for example comprising hole
Implanted layer, hole transmission layer, luminescent layer, electron transfer layer, electron injecting layer etc..
It is lasting to require exploitation organic film material in order to improve performance, service life or the efficiency of organic illuminating element.
Summary of the invention
This specification provides heterocyclic compound and the organic illuminating element comprising it.
One embodiment of this specification provides the heterocyclic compound indicated by following chemical formula 1.
[chemical formula 1]
In above-mentioned chemical formula 1,
R5 to R8 is same or different to each other, and is each independently hydrogen, deuterium, halogen group, itrile group, nitro, hydroxyl, fragrant oxygen
Base, alkyl sulfenyl (Alkyl thioxy), artyl sulfo (Aryl
Thioxy), alkyl sulfoxide base (Alkyl sulfoxy), aryl sulfoxid es base (
Aryl sulfoxy), silicyl, boryl, substituted or unsubstituted alkyl, substituted or unsubstituted naphthenic base, substitution or not
Substituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted aryl alkyl, substituted or unsubstituted alkyl amine group,
Substituted or unsubstituted aralkyl amido, substituted or unsubstituted heteroaryl amido, substituted or unsubstituted arylamine group, substitution
Or unsubstituted aryl heteroaryl amido, substituted or unsubstituted aryl phosphino- or substituted or unsubstituted heterocycle,
L1 and L2 are same or different to each other, and are each independently Direct Bonding, substituted or unsubstituted arlydene or take
The heterocycle of generation or unsubstituted divalent,
Ar1 is substituted or unsubstituted heterocycle,
R1 to R4 is same or different to each other, and is each independently substituted or unsubstituted aryl or substituted or unsubstituted
Heterocycle,
A and b is respectively 0 to 4 integer,
The integer that c is 0 to 3,
The integer that d is 0 to 5,
When a to d is respectively 2 or more, the substituent group in bracket is same or different to each other,
N1 and n2 is 0 or 1,
1 in n1 and n2 the above are 1 integer,
X1 and X2 is hydrogen or is bonded directly with one another.
In addition, an embodiment of this specification provides a kind of organic illuminating element, characterized by comprising: the first electricity
Pole, second electrode and have 1 layer or more of organic matter layer between above-mentioned first electrode and second electrode, it is above-mentioned organic
1 layer or more in nitride layer includes above-mentioned heterocyclic compound.
The compound recorded in this specification can be used as the material of the organic matter layer of organic illuminating element.According at least one
Raising, lower driving voltage and/or the service life that the compound of embodiment can be realized efficiency in organic illuminating element are special
The raising of property.The compound recorded in this specification can be used as hole injection, hole transport, hole injection and hole transport,
Electronics inhibits, shines, hole inhibits, electron-transport or electron injection material and use.
Detailed description of the invention
Fig. 1 illustrates the examples for the organic illuminating element being made of substrate 1, anode 2, luminescent layer 3 and cathode 4.
Fig. 2 is illustrated by substrate 1, anode 2, hole injection layer 5, hole transmission layer 6, luminescent layer 3,7 and of electron transfer layer
The example for the organic illuminating element that cathode 4 is constituted.
1: substrate
2: anode
3: luminescent layer
4: cathode
5: hole injection layer
6: hole transmission layer
7: electron transfer layer
Specific embodiment
Hereinafter, being illustrated in more details to this specification.
One embodiment of this specification provides the compound indicated by following chemical formula 1.
[chemical formula 1]
In above-mentioned chemical formula 1,
R5 to R8 is same or different to each other, and is each independently hydrogen, deuterium, halogen group, itrile group, nitro, hydroxyl, fragrant oxygen
Base, alkyl sulfenyl, artyl sulfo, alkyl sulfoxide base, aryl sulfoxid es base, silicyl, boryl, substituted or unsubstituted alkyl,
Substituted or unsubstituted naphthenic base, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted aryl
Alkyl, substituted or unsubstituted alkyl amine group, substituted or unsubstituted aralkyl amido, substituted or unsubstituted heteroaryl amine
Base, substituted or unsubstituted arylamine group, substituted or unsubstituted aryl heteroaryl amido, substituted or unsubstituted aryl phosphine
Base or substituted or unsubstituted heterocycle,
L1 and L2 are same or different to each other, and are each independently Direct Bonding, substituted or unsubstituted arlydene or take
The heterocycle of generation or unsubstituted divalent,
Ar1 is substituted or unsubstituted heterocycle,
R1 to R4 is same or different to each other, and is each independently substituted or unsubstituted aryl or substituted or unsubstituted
Heterocycle,
A and b is respectively 0 to 4 integer,
The integer that c is 0 to 3,
The integer that d is 0 to 5,
When a to d is respectively 2 or more, the substituent group in bracket is same or different to each other,
N1 and n2 is 0 or 1,
1 in n1 and n2 the above are 1 integer,
X1 and X2 is hydrogen or is bonded directly with one another.
The illustration of above-mentioned substituent group is illustrated below, but not limited to this.
In this specification, above-mentioned " substitution " this term refers to that the hydrogen atom in conjunction with the carbon atom of compound is replaced by
Other substituent groups, as long as substituted position hydrogen atom can with substituted position, i.e., substituent group can substituted position just
It does not limit, in 2 or more substituted situations, 2 or more substituent groups be can be the same or different from each other.
In this specification, " substituted or unsubstituted " this term refers to by selected from deuterium, halogen group, itrile group, nitro, boron
It is base, substituted or unsubstituted alkyl, substituted or unsubstituted naphthenic base, substituted or unsubstituted alkoxy, substituted or unsubstituted
Aryloxy group, substituted or unsubstituted alkenyl, substituted or unsubstituted silicyl, substituted or unsubstituted amido, substitution or
1 or more substituent group in unsubstituted aryl and substituted or unsubstituted heterocycle replaces, or foregoing illustrative
The substituent group that 2 or more substituent groups in substituent group are formed by connecting replaces, or does not have any substituent group.For example, " 2
The substituent group that above substituent group is formed by connecting " can be the aryl being substituted with aryl, the aryl being substituted by heteroaryl, by aryl
Substituted heterocycle, by alkyl-substituted aryl etc..
In this specification, " adjacent " group can refer on the atom being directly connected to the atom replaced by the substituent group
It the substituent group that is replaced or immediate substituent group or is taken by the substituent group in stereochemical structure with the substituent group
The other substituent groups replaced on the atom in generation.For example, 2 substituent groups that the ortho position (ortho) in phenyl ring replaces and
2 substituent groups replaced on same carbon in aliphatic ring are considered as " adjacent " group each other.
In this specification, " * " andRefer to the position in conjunction with chemical formula 1 or nuclear structure.
In this specification, as the example of halogen group, there are fluorine, chlorine, bromine or iodine.
In this specification, silicyl can be by-SiRaRbRcChemical formula indicate, above-mentioned Ra、RbAnd RcCan be respectively
Hydrogen, substituted or unsubstituted alkyl or substituted or unsubstituted aryl.Above-mentioned silicyl specifically has trimethyl silyl
Base, triethylsilyl, t-butyldimethylsilyl, vinyldimethylsilyl, propyl-dimethyl monosilane
Base, triphenyl-silyl, diphenylsilyl group, phenyl silyl groups etc., but not limited to this.
In this specification, boryl can be by-BRaRbChemical formula indicate, above-mentioned RaAnd RbRespectively can for hydrogen, replace or
Unsubstituted alkyl or substituted or unsubstituted aryl.Above-mentioned boryl specifically has trimethyl boryl, triethyl group boryl, tertiary fourth
Base dimethyl boryl, triphenyl boryl, phenyl boryl etc., but not limited to this.
In this specification, abovementioned alkyl can be linear chain or branched chain, and carbon atom number is not particularly limited, and can be 1 to 50,
According to an embodiment, carbon atom number can be 1 to 30, and according to another embodiment, carbon atom number can be 1 to 20.Make
For specific example, there are methyl, ethyl, propyl, n-propyl, isopropyl, butyl, normal-butyl, isobutyl group, tert-butyl, sec-butyl, 1-
Methyl-butvl, 1- Ethyl-butyl, amyl, n-pentyl, isopentyl, neopentyl, tertiary pentyl, hexyl, n-hexyl, 1- methylpent
Base, 2- methyl amyl, 4- methyl -2- amyl, 3,3- dimethylbutyl, 2- ethyl-butyl, heptyl, n-heptyl, 1- methylhexyl,
Cyclopentyl-methyl, cyclohexyl methyl, octyl, n-octyl, t-octyl, 1- methylheptyl, 2- ethylhexyl, 2- propylpentyl, just
Nonyl, 2,2- dimethyl heptyl, 1- Ethyl-propyl, 1,1- Dimethyl-propyl, isohesyl, 2- methyl amyl, 4- methylhexyl,
5- methylhexyl etc., but not limited to this.
In this specification, naphthenic base is not particularly limited, and carbon atom number can be 3 to 60, and according to an embodiment, carbon is former
Subnumber can be 3 to 30, and according to another embodiment, carbon atom number can be 3 to 20.Specifically, having cyclopropyl, ring fourth
Base, cyclopenta, 3- methylcyclopentyl, 2,3- dimethylcyclopentyl, cyclohexyl, 3- methylcyclohexyl, 4- methylcyclohexyl, 2,3-
Dimethylcyclohexyl, 3,4,5- trimethylcyclohexyls, 4- tert-butylcyclohexyl, suberyl, cyclooctyl etc., but be not limited to
This.
In this specification, above-mentioned alkoxy can be straight chain, branch or ring-type.The carbon atom number of alkoxy does not limit especially
Fixed, preferably carbon atom number is 1 to 20.Specifically, can be methoxyl group, ethyoxyl, positive propoxy, isopropoxy, isopropyl oxygen
Base, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyl oxygen, isoamoxy, positive hexyloxy, 3,
3- dimethyl butyrate oxygroup, 2- ethyl-butoxy, n-octyloxy, positive nonyl epoxide, n-decyloxy, benzyloxy, to methylbenzyloxy etc.,
But not limited to this.
In this specification, amido can be selected from-NH2, alkyl amine group, N- aryl alkyl amido, arylamine group, N- aryl it is miscellaneous
Arylamine group, N- miscellaneous alkyl aryl amido and heteroaryl amido, carbon atom number are not particularly limited, and preferably 1 to 30.As amine
The specific example of base has methylamino, dimethyl amido, ethyl amido, diethyl amido, phenyl amido, naphthalene amido, biphenyl
Base amido, anthryl amido, 9- methyl-anthryl amido, diphenyl amido, N- phenyl napthyl amido, ditolyl base amido, N- phenyl
Tolyl amido, triphenyl amido etc., but not limited to this.
In this specification, above-mentioned alkenyl can be linear chain or branched chain, and carbon atom number is not particularly limited, preferably 2 to 40.
As specific example, have vinyl, 1- acrylic, isopropenyl, 1- cyclobutenyl, 2- cyclobutenyl, 3- cyclobutenyl, 1- pentenyl,
2- pentenyl, 3- pentenyl, 3-methyl-1-butene base, 1,3- butadienyl, allyl, 1- phenyl vinyl -1- base, 2- benzene
Base vinyl -1- base, 2,2- diphenylacetylene -1- base, 2- phenyl -2- (naphthalene -1- base) vinyl -1- base, 2,2- bis- (two
Phenyl -1- base) vinyl -1- base, Stilbene base, styryl etc., but not limited to this.
In this specification, the carbon atom number of alkyl amine group is not particularly limited, and can be 1 to 40, according to an embodiment,
Carbon atom number can be 1 to 30, and according to another embodiment, carbon atom number can be 1 to 20.Concrete example as alkyl amine group
Son has methylamino, dimethyl amido, ethyl amido, diethyl amido, phenyl amido, naphthalene amido, xenyl amido, anthracene
Base amido, 9- methyl-anthryl amido, diphenyl amido, phenyl napthyl amido, ditolyl base amido, phenyltoluene base amido, three
Phenyl amido etc., but not limited to this.
It is substituted or unsubstituted monoarylamine base, substituted or unsubstituted as the example of arylamine group in this specification
Diaryl amido or substituted or unsubstituted triaryl amido.Aryl in above-mentioned arylamine group can be monocyclic aryl,
It may be polyaromatic.It is above-mentioned to include that the arylamine group of 2 or more aryl may include monocyclic aryl, polyaromatic, or
Person includes simultaneously monocyclic aryl and polyaromatic.
As the specific example of arylamine group, there are phenyl amido, naphthalene amido, xenyl amido, anthryl amido, 3- first
Base-phenyl amido, 4- methyl-naphthalene amido, 2- Methvl-biphenyl amido, 9- methyl-anthryl amido, diphenyl amido, phenyl
Naphthalene amido, ditolyl base amido, phenyltoluene base amido and triphenyl amido etc., but not limited to this.
In this specification, as the example of heteroaryl amido, substituted or unsubstituted single heteroaryl amido replaces or not
Substituted di (hetero) arylamine group or substituted or unsubstituted three heteroaryls amido.Heteroaryl in above-mentioned heteroaryl amido can
Think bicyclic heteroaryl, or polyheteroaromatic.Above-mentioned includes that the heteroaryl amido of 2 or more heteroaryls may include
Bicyclic heteroaryl, polyheteroaromatic, or simultaneously include bicyclic heteroaryl and polyheteroaromatic.
In this specification, aryl heteroaryl amido refers to the amido replaced by aryl and heteroaryl.
It is substituted or unsubstituted single aryl phosphino-, substituted or unsubstituted as the example of aryl phosphino- in this specification
Diarylphosphino or substituted or unsubstituted triaryl phosphino-.Aryl in above-mentioned aryl phosphino- can be monocyclic aryl,
It may be polyaromatic.It is above-mentioned include 2 or more aryl aryl phosphino- can for monocyclic aryl, polyaromatic, or
It simultaneously include monocyclic aryl and polyaromatic.
In this specification, in the case that above-mentioned aryl is monocyclic aryl, carbon atom number is not particularly limited, carbon atom number
It can be 6 to 60, according to an embodiment, carbon atom number can be 6 to 30, and according to another embodiment, carbon atom number can be with
It is 6 to 20.As the specific example of above-mentioned monocyclic aryl, can there are phenyl, xenyl, terphenyl etc., but be not limited to
This.
When above-mentioned aryl be polyaromatic in the case where, carbon atom number is not particularly limited, carbon atom number can for 10 to
60, according to an embodiment, carbon atom number can be 10 to 30, and according to another embodiment, carbon atom number can be 10 to 20.
Specifically, as polyaromatic, can for naphthalene, anthryl, phenanthryl, pyrenyl, base,Base, fluorenyl etc., but be not limited to
This.
In this specification, above-mentioned fluorenyl can be substituted, and adjacent substituent group can be bonded to each other and form ring.
In the substituted situation of above-mentioned fluorenyl, Ke Yiwei Deng.But not limited to this.
In this specification, heterocycle includes the hetero atom of 1 or more non-carbon, specifically, above-mentioned hetero atom can be with
Atom comprising 1 or more in O, N, Se and S.The carbon atom number of heterocycle is not particularly limited, but carbon atom number can be with
It is 2 to 60.According to an embodiment, carbon atom number can be 2 to 30.According to another embodiment, carbon atom number can for 2 to
20.As the example of heterocycle, have thienyl, furyl, pyrrole radicals, imidazole radicals, thiazolyl,Oxazolyl,Di azoly, three
Oxazolyl, pyridyl group, bipyridyl, pyrimidine radicals, triazine radical, acridinyl, pyridazinyl, pyrazinyl, quinolyl, quinazolyl, quinoline
Quinoline base, phthalazinyl, Pyridopyrimidine base, pyrido-pyrazine base, pyrazine and pyrazinyl, isoquinolyl, indyl, carbazyl, benzene
AndOxazolyl, benzimidazolyl, benzoquinoline base, benzo pyridazinyl, benzothiazolyl, benzo carbazole base, benzothienyl,
It is dibenzothiophene, benzofuranyl, phenanthroline (phenanthroline), thiazolyl, differentOxazolyl,Di azoly,
Thiadiazolyl group, benzothiazolyl, phenothiazinyl and dibenzofuran group, benzimidazole and naphthalene, phenanthro- imidazole radicals, benzimidazole
And phenanthridinyl etc., but not limited to this.
Above-mentioned heterocycle can be monocycle or polycyclic, or aromatic series, aliphatic or aromatic series with it is aliphatic thick
Ring.
In this specification, above-mentioned hydrocarbon ring can be aliphatic, aromatic series or aliphatic and aromatic condensed ring, above-mentioned
Hydrocarbon ring can be selected from the illustration of above-mentioned naphthenic base or aryl other than not being 1 valence.Above-mentioned heterocycle can be aliphatic, fragrance
Race or aliphatic and aromatic condensed ring can be selected from the illustration of above-mentioned heterocycle other than not being 1 valence.
In this specification, aryloxy group, artyl sulfo, aryl sulfoxid es base, aryl phosphino-, aryl alkyl, aralkyl amido, virtue
Alkenyl, alkylaryl, arylamine group, the aryl in aryl heteroaryl amido can be applicable in the above-mentioned explanation about aryl.
In this specification, alkyl sulfenyl, alkyl sulfoxide base, aryl alkyl, aralkyl amido, alkylaryl, alkyl amine group
In alkyl can be applicable in the above-mentioned explanation about alkyl.
In this specification, heteroaryl, heteroaryl amido, the heteroaryl in aryl heteroaryl amido can be applicable in above-mentioned pass
In the explanation of heterocycle.
In this specification, the alkenyl in arylalkenyl, aryl alkenyl can be applicable in the above-mentioned explanation about alkenyl.
In this specification, the alkyl in aryl alkyl, alkylthio can be applicable in the above-mentioned explanation about alkyl.
In this specification, arlydene can be applicable in the above-mentioned explanation about aryl other than being divalent.
In this specification, heteroarylidene can be applicable in the above-mentioned explanation about heteroaryl other than being divalent.
In an embodiment of this specification, above-mentioned X1 and X2 are hydrogen.
In another embodiment, above-mentioned X1 and X2 are bonded directly with one another and form five-membered ring.
In one embodiment of this specification, above-mentioned n1 and n2 are 0 or 1, and the above are 1 integers by 1 in n1 and n2.
According to another embodiment, integer that above-mentioned n1 and n2 are 1.
In one embodiment of this specification, above-mentioned Ar1 is the heterocycle of substituted or unsubstituted carbon atom number 2 to 60.
In one embodiment of this specification, above-mentioned Ar1 is the heterocycle of substituted or unsubstituted carbon atom number 2 to 40.
In one embodiment of this specification, above-mentioned Ar1-L2-NR3R4 is one of following structures.
In above structure,
Defining for L2, R3 and R4 is identical as the definition in above-mentioned chemical formula 1,
R' and R " are same or different to each other, and are each independently hydrogen, deuterium, halogen group, itrile group, nitro, hydroxyl, fragrant oxygen
Base, alkyl sulfenyl, artyl sulfo, alkyl sulfoxide base, aryl sulfoxid es base, silicyl, boryl, substituted or unsubstituted alkyl,
Substituted or unsubstituted naphthenic base, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted aryl
Alkyl, substituted or unsubstituted alkyl amine group, substituted or unsubstituted aralkyl amido, substituted or unsubstituted heteroaryl amine
Base, substituted or unsubstituted arylamine group, substituted or unsubstituted aryl heteroaryl amido, substituted or unsubstituted aryl phosphine
Base or substituted or unsubstituted heterocycle,
Above structure can be further substituted.
In an embodiment of this specification, above-mentioned R' and R " are same or different to each other, be each independently hydrogen, deuterium,
It is halogen group, silicyl, boryl, substituted or unsubstituted alkyl, substituted or unsubstituted naphthenic base, substituted or unsubstituted
Aryl, substituted or unsubstituted alkyl amine group, substituted or unsubstituted aralkyl amido, substituted or unsubstituted heteroaryl amine
Base, substituted or unsubstituted arylamine group, substituted or unsubstituted aryl heteroaryl amido or substituted or unsubstituted heterocycle
Base.
In an embodiment of this specification, above-mentioned R' and R " are same or different to each other, be each independently hydrogen, deuterium,
Substituted or unsubstituted alkyl, substituted or unsubstituted naphthenic base, substituted or unsubstituted aryl or substituted or unsubstituted
Heterocycle.
In one embodiment of this specification, above-mentioned R' and R " are same or different to each other, and are each independently hydrogen, deuterium, take
Generation or the alkyl of unsubstituted carbon atom number 1 to 50, substituted or unsubstituted carbon atom number 3 to 60 naphthenic base, replace or not
The heterocycle of the aryl of substituted carbon atom number 6 to 60 or substituted or unsubstituted carbon atom number 2 to 40.
In one embodiment of this specification, above-mentioned R' and R " are same or different to each other, and are each independently hydrogen, deuterium, take
Generation or the alkyl of unsubstituted carbon atom number 1 to 30, substituted or unsubstituted carbon atom number 3 to 30 naphthenic base, replace or not
The heterocycle of the aryl of substituted carbon atom number 6 to 30 or substituted or unsubstituted carbon atom number 2 to 25.
In another embodiment, above-mentioned R' and R " are same or different to each other, and are each independently substituted or unsubstituted
The alkyl of carbon atom number 1 to 20.
According to another embodiment, above-mentioned R' and R " are same or different to each other, and are each independently substituted or unsubstituted
Methyl, substituted or unsubstituted ethyl or substituted or unsubstituted tert-butyl.
In another embodiment, above-mentioned R' and R " are same or different to each other, and are each independently methyl, ethyl or tertiary fourth
Base.
According to an embodiment of this specification, the heterocyclic compound indicated by above-mentioned chemical formula 1 can be for selected from following
Chemical formula 1-A is any into 1-D.
[chemical formula 1-A]
[chemical formula 1-B]
[chemical formula 1-C]
[chemical formula 1-D]
Above-mentioned chemical formula 1-A into 1-D,
X1, X2, R1 are identical as the definition in above-mentioned chemical formula 1 to R8, L1, L2, n1 and n2,
W1 to W4 is same or different to each other, and is each independently O, S or SiT1T2,
T1, T2, R101 are same or different to each other to R104, be each independently hydrogen, deuterium, substituted or unsubstituted alkyl,
Substituted or unsubstituted naphthenic base, substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl,
S1 and s3 is respectively 0 to 5 integer,
S2 and s4 is respectively 0 to 7 integer,
When s1 to s4 is respectively 2 or more integer, the substituent group in bracket is same or different to each other.
According to an embodiment of this specification, above-mentioned s1 is 0 or 1.
According to an embodiment of this specification, above-mentioned s2 is 0 or 1.
According to an embodiment of this specification, above-mentioned s3 is 0 or 1.
According to an embodiment of this specification, above-mentioned s4 is 0 or 1.
In another embodiment, above-mentioned T1 and T2 are same or different to each other, and are each independently hydrogen or substitution or not
Substituted alkyl.
According to another embodiment, above-mentioned T1 and T2 are same or different to each other, and are each independently hydrogen or substitution or not
The alkyl of substituted carbon atom number 1 to 40.
In another embodiment, above-mentioned T1 and T2 are same or different to each other, and are each independently hydrogen or substitution or not
The alkyl of substituted carbon atom number 1 to 20.
According to another embodiment, above-mentioned T1 and T2 are same or different to each other, and are each independently hydrogen, substituted or unsubstituted
Methyl, substituted or unsubstituted ethyl or substituted or unsubstituted tert-butyl.
In another embodiment, above-mentioned T1 and T2 is methyl.
In an embodiment of this specification, above-mentioned R101 to R104 is same or different to each other, be each independently hydrogen,
Substituted or unsubstituted alkyl or substituted or unsubstituted aryl.
According to another embodiment, above-mentioned R101 to R104 is same or different to each other, be each independently hydrogen, replace or not
The aryl of the alkyl of substituted carbon atom number 1 to 40 or substituted or unsubstituted carbon atom number 6 to 60.
In another embodiment, above-mentioned R101 to R104 is same or different to each other, be each independently hydrogen, replace or not
The aryl of the alkyl of substituted carbon atom number 1 to 20 or substituted or unsubstituted carbon atom number 6 to 30.
According to another embodiment, above-mentioned R101 to R104 is hydrogen.
In an embodiment of this specification, above-mentioned R5 to R8 is same or different to each other, be each independently hydrogen, deuterium,
It is halogen group, silicyl, boryl, substituted or unsubstituted alkyl, substituted or unsubstituted naphthenic base, substituted or unsubstituted
Aryl, substituted or unsubstituted alkyl amine group, substituted or unsubstituted aralkyl amido, substituted or unsubstituted heteroaryl amine
Base, substituted or unsubstituted arylamine group, substituted or unsubstituted aryl heteroaryl amido or substituted or unsubstituted heterocycle
Base.
In an embodiment of this specification, above-mentioned R5 to R8 is same or different to each other, be each independently hydrogen, deuterium,
Substituted or unsubstituted alkyl, substituted or unsubstituted naphthenic base, substituted or unsubstituted aryl or substituted or unsubstituted
Heterocycle.
In an embodiment of this specification, above-mentioned R5 to R8 is same or different to each other, be each independently hydrogen, deuterium,
The alkyl of substituted or unsubstituted carbon atom number 1 to 50, substituted or unsubstituted carbon atom number 3 to 60 naphthenic base, replace or
The heterocycle of the aryl of unsubstituted carbon atom number 6 to 60 or substituted or unsubstituted carbon atom number 2 to 40.
In an embodiment of this specification, above-mentioned R5 to R8 is same or different to each other, be each independently hydrogen, deuterium,
The alkyl of substituted or unsubstituted carbon atom number 1 to 30, substituted or unsubstituted carbon atom number 3 to 30 naphthenic base, replace or
The heterocycle of the aryl of unsubstituted carbon atom number 6 to 30 or substituted or unsubstituted carbon atom number 2 to 25.
In another embodiment, above-mentioned R5 to R8 is same or different to each other, and is each independently hydrogen, deuterium, substitution or not
The alkyl of substituted carbon atom number 1 to 30, the aryl of substituted or unsubstituted carbon atom number 6 to 30 or substituted or unsubstituted
Carbon atom number 2 to 25 heterocycle.
According to another embodiment, above-mentioned R5 to R8 is same or different to each other, and is each independently hydrogen, deuterium, substitution or not
Substituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl, substitution or
Unsubstituted xenyl, substituted or unsubstituted naphthalene or substituted or unsubstituted dibenzofuran group.
In another embodiment, above-mentioned R5 to R8 is same or different to each other, and is each independently hydrogen, deuterium, methyl, second
Base, tert-butyl, phenyl, xenyl, naphthalene or dibenzofuran group.
According to another embodiment, above-mentioned R5 and R8 are hydrogen.
In an embodiment of this specification, above-mentioned L1 and L2 are same or different to each other, and are each independently direct key
The divalent of conjunction, the arlydene of substituted or unsubstituted carbon atom number 6 to 30 or substituted or unsubstituted carbon atom number 2 to 30
Heterocycle.
In another embodiment, above-mentioned L1 and L2 are same or different to each other, and are each independently substituted or unsubstituted
Phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted sub- terphenyl, substituted or unsubstituted naphthylene,
It is substituted or unsubstituted fluorenylidene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted anthrylene, substituted or unsubstituted
Triphenylene, substituted or unsubstituted sub- thienyl, substituted or unsubstituted furylidene, substituted or unsubstituted sub- pyrroles
Base, substituted or unsubstituted sub- dibenzofuran group, substituted or unsubstituted dibenzo Asia thienyl or substituted or unsubstituted
Sub- carbazyl.
According to another embodiment, above-mentioned L1 and L2 are same or different to each other, and are each independently phenylene, sub- biphenyl
Base, sub- terphenyl, naphthylene, 9,9- diphenyl fluorenyl, 9,9- dimethyl fluorenyl, phenanthrylene, anthrylene, triphenylene, Asia
Thienyl, furylidene, by the substituted or unsubstituted sub- pyrrole radicals of methyl or phenyl, sub- dibenzofuran group, dibenzo Asia thiophene
Pheno base, by the substituted or unsubstituted sub- carbazyl of ethyl or phenyl.
In an embodiment of this specification, above-mentioned L1 and L2 are same or different to each other, and are each independently direct key
One of conjunction or following structures.
In an embodiment of this specification, above-mentioned L1 and L2 are Direct Bonding.
In an embodiment of this specification, above-mentioned R1 to R4 is same or different to each other, be each independently substitution or
Unsubstituted aryl or substituted or unsubstituted heterocycle.
According to an embodiment of this specification, above-mentioned R1 to R4 is same or different to each other, be each independently substitution or
The heterocycle of the aryl of unsubstituted carbon atom number 6 to 30 or substituted or unsubstituted carbon atom number 2 to 30.
In another embodiment, above-mentioned R1 to R4 is same or different to each other, and is each independently substituted or unsubstituted
The heterocycle of the aryl of carbon atom number 6 to 30 or substituted or unsubstituted carbon atom number 2 to 30.
According to another embodiment, above-mentioned R1 to R4 is same or different to each other, and is each independently substituted or unsubstituted
The heterocycle of the aryl of carbon atom number 6 to 30 or substituted or unsubstituted carbon atom number 2 to 30.
According to another embodiment, above-mentioned R1 to R4 is same or different to each other, and is each independently substituted or unsubstituted
Phenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted xenyl, substituted or unsubstituted terphenyl, substitution or not
Substituted anthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted fluoranthene base, takes substituted or unsubstituted phenanthryl
In generation, is unsubstitutedBase, substituted or unsubstituted pyrenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted indenofluorene
Base, substituted or unsubstituted benzo fluorenyl, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrazinyl, substitution or not
Substituted pyridazinyl, substituted or unsubstituted pyrimidine radicals, substituted or unsubstituted quinolyl, substituted or unsubstituted quinoxaline
Base, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted dibenzofuran group, substitution
Or unsubstituted dibenzothiophene, substituted or unsubstituted naphtho- benzofuranyl, substituted or unsubstituted naphtho- benzo thiophene
Pheno base, substituted or unsubstituted benzofuranyl, substituted or unsubstituted benzothienyl, substituted or unsubstituted benzimidazole
Base, substituted or unsubstituted benzoOxazolyl, substituted or unsubstituted benzothiazolyl, substituted or unsubstituted fluorenes and benzo
Furyl or substituted or unsubstituted benzofuran and dibenzofuran group.
In an embodiment of this specification, above-mentioned R1 to R4 is same or different to each other, and is each independently and is selected from down
State one of structure.
In above structure,
R201 to R297 is same or different to each other, and is each independently hydrogen, deuterium, halogen group, itrile group, nitro, monosilane
Base, boryl, substituted or unsubstituted amido, substituted or unsubstituted alkyl, substituted or unsubstituted naphthenic base, substitution do not take
The aryl in generation or substituted or unsubstituted heteroaryl,
A1, a6, a10, a23 and a25 are respectively 0 to 5 integer,
A2, a5, a8, a9, a14, a16, a17, a21, a28 are to a35, b1 to b4, b6 to b9, b11 to b13, b15 and b17
It is respectively 0 to 4 integer to b32,
A3 and a22 is respectively 0 to 7 integer,
A4, a7, a12, a15, a19, a26 and a27 are respectively 0 to 3 integer,
The integer that a11 is 0 to 9,
A13, a20 and a24 are respectively 0 to 6 integer,
A18, b5, b10, b14 and b16 are respectively 0 to 2 integer,
In the case that a18, b5, b10, b14 and b16 are 2, the substituent group in bracket is different from each other,
A1, a6, a10, a23, a25, a2, a5, a8, a9, a14, a16, a17, a21, a28 to a35, b1 to b4, b6 to b9,
B11 is respectively to b13, b15, b17 to b32, a3, a22, a4, a7, a12, a15, a19, a26, a27, a11, a13, a20 and a24
When 2 or more, the substituent group in bracket is same or different to each other.
In an embodiment of this specification, above-mentioned R201 to R297 is same or different to each other, be each independently hydrogen,
Deuterium, halogen group, silicyl, substituted or unsubstituted alkyl, substituted or unsubstituted naphthenic base or substituted or unsubstituted
Aryl.
In another embodiment, above-mentioned R201 to R297 is same or different to each other, and is each independently hydrogen, deuterium, halogen
Group, silicyl, the alkyl of substituted or unsubstituted carbon atom number 1 to 30, substituted or unsubstituted carbon atom number 3 to 30
The aryl of naphthenic base or substituted or unsubstituted carbon atom number 6 to 30.
In another embodiment, above-mentioned R201 to R297 is same or different to each other, and is each independently hydrogen, deuterium, halogen
Group, silicyl, the alkyl of substituted or unsubstituted carbon atom number 1 to 20, substituted or unsubstituted carbon atom number 3 to 20
The aryl of naphthenic base or substituted or unsubstituted carbon atom number 6 to 20.
In another embodiment, above-mentioned R201 to R297 is same or different to each other, and is each independently hydrogen, deuterium, halogen
Group, by the substituted or unsubstituted silicyl of alkyl, substituted or unsubstituted carbon atom number 1 to 20 alkyl, replace or not
The aryl of the naphthenic base of substituted carbon atom number 3 to 20 or substituted or unsubstituted carbon atom number 6 to 20.
According to another embodiment, above-mentioned R201 to R297 is same or different to each other, and is each independently hydrogen, deuterium, halogen
Group, by methyl substituted silicyl, substituted or unsubstituted methyl, substituted or unsubstituted ethyl, substituted or unsubstituted
Propyl, substituted or unsubstituted tert-butyl, substituted or unsubstituted phenyl, substituted or unsubstituted xenyl, substitution or not
Substituted cyclopenta or substituted or unsubstituted cyclohexyl.
In another embodiment, above-mentioned R201 to R297 is same or different to each other, and is each independently hydrogen, deuterium, fluorine
(F), trimethyl silyl, methyl, tert-butyl, phenyl or xenyl.
In an embodiment of this specification, above-mentioned a1 to a35 and b1 to b32 are respectively 0 to 2 integer.
In an embodiment of this specification, above-mentioned R1 to R4 is same or different to each other, be each independently fluorine (- F),
Methyl, by tert-butyl or the substituted or unsubstituted phenyl of trimethyl silyl, 9,9- dimethyl fluorenyl, naphthalene or dibenzo furan
It mutters base.
According to an embodiment of specification, the heterocyclic compound of above-mentioned chemical formula 1 can be for selected from following heterocyclic compounds
Any one of object.
It can be manufactured by aftermentioned manufacturing method according to the compound of an embodiment of this specification.Such as above-mentionedization
The compound of formula 1 can manufacture nuclear structure as following Production Examples.Substituent group can be by well known to the technical field
Method combines, and type, position or the number of substituent group can the technology alterations according to well known to the technical field.
According to an embodiment of this specification, a kind of organic illuminating element can be provided, comprising: first electrode, with it is upper
It states that first electrode is opposed and the second electrode that has and has 1 layer or more between above-mentioned first electrode and second electrode
Organic matter layer, 1 layer or more in above-mentioned organic matter layer includes above-mentioned heterocyclic compound.
According to an embodiment of this specification, the organic matter layer of the organic illuminating element of this specification can be by single layer knot
It is configured to, can also be formed by the multilayered structure for being laminated with two layers or more of organic matter layer.For example, organic light emission member of the invention
Part can have comprising hole injection layer, hole transmission layer, electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer,
The structure as organic matter layer such as electronic implanted layer.But it's not limited to that for the structure of organic illuminating element, can wrap
Containing less or more organic layer.
Organic luminous element structure of the invention can have structure as depicted in figs. 1 and 2, and but not limited to this.
The knot for being sequentially laminated with the organic illuminating element of anode 2, luminescent layer 3 and cathode 4 on substrate 1 is instantiated in Fig. 1
Structure.In this configuration, above compound may be embodied in above-mentioned luminescent layer 3.
Instantiated in Fig. 2 be sequentially laminated on substrate 1 anode 2, hole injection layer 5, hole transmission layer 6, luminescent layer 3,
The structure of the organic illuminating element of electron transfer layer 7 and cathode 4.In this configuration, above compound may be embodied in above-mentioned
In hole injection layer 5, hole transmission layer 6, luminescent layer 3 or electron transfer layer 7.
According to an embodiment of this specification, above-mentioned organic matter layer includes hole injection layer, hole transmission layer or electronics
Barrier layer, above-mentioned hole injection layer, hole transmission layer or electronic barrier layer include the heterocyclic compound indicated by above-mentioned chemical formula 1
Object.
According to an embodiment of this specification, above-mentioned organic matter layer includes luminescent layer, and above-mentioned luminescent layer includes by above-mentioned
The heterocyclic compound that chemical formula 1 indicates.
According to an embodiment of this specification, above-mentioned organic matter layer includes luminescent layer, and above-mentioned luminescent layer includes by above-mentioned
The heterocyclic compound that chemical formula 1 indicates, above-mentioned luminescent layer also includes the compound indicated by following chemical formula 2.
[chemical formula 2]
In above-mentioned chemical formula 2,
R9 is hydrogen, deuterium, halogen group, itrile group, nitro, hydroxyl, aryloxy group, alkyl sulfenyl, artyl sulfo, alkyl sulfoxide
Base, aryl sulfoxid es base, silicyl, boryl, substituted or unsubstituted alkyl, substituted or unsubstituted naphthenic base, substitution or not
Substituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted aryl alkyl, substituted or unsubstituted alkyl amine group,
Substituted or unsubstituted aralkyl amido, substituted or unsubstituted heteroaryl amido, substituted or unsubstituted arylamine group, substitution
Or unsubstituted aryl heteroaryl amido, substituted or unsubstituted aryl phosphino- or substituted or unsubstituted heterocycle,
The integer that p is 0 to 6,
When p is 2 or more, the substituent group in bracket is same or different to each other,
L3 to L6 is same or different to each other, be each independently Direct Bonding or substituted or unsubstituted arlydene or
The substituted or unsubstituted heteroarylidene of person,
Ar2 to Ar5 is same or different to each other, and is each independently hydrogen, substituted or unsubstituted aryl or substitution or not
Substituted heteroaryl.
According to an embodiment of this specification, above-mentioned R9 be hydrogen, deuterium, halogen group, silicyl, boryl, substitution or
Unsubstituted alkyl, substituted or unsubstituted naphthenic base, substituted or unsubstituted aryl, substituted or unsubstituted alkyl amine group,
Substituted or unsubstituted aralkyl amido, substituted or unsubstituted heteroaryl amido, substituted or unsubstituted arylamine group, substitution
Or unsubstituted aryl heteroaryl amido or substituted or unsubstituted heterocycle.
In an embodiment of this specification, above-mentioned R9 is same or different to each other, and is each independently hydrogen, deuterium, substitution
Or unsubstituted alkyl, substituted or unsubstituted naphthenic base, substituted or unsubstituted aryl or substituted or unsubstituted heterocycle
Base.
In an embodiment of this specification, above-mentioned R9 is same or different to each other, and is each independently hydrogen, deuterium, substitution
Or the alkyl of unsubstituted carbon atom number 1 to 50, substituted or unsubstituted carbon atom number 3 to 60 naphthenic base, replace or do not take
The heterocycle of the aryl of the carbon atom number 6 to 60 in generation or substituted or unsubstituted carbon atom number 2 to 40.
In an embodiment of this specification, above-mentioned R9 is same or different to each other, and is each independently hydrogen, deuterium, substitution
Or the alkyl of unsubstituted carbon atom number 1 to 30, substituted or unsubstituted carbon atom number 3 to 30 naphthenic base, replace or do not take
The heterocycle of the aryl of the carbon atom number 6 to 30 in generation or substituted or unsubstituted carbon atom number 2 to 25.
According to another embodiment, above-mentioned R9 is hydrogen.
In an embodiment of this specification, above-mentioned p is 0 or 1.
In an embodiment of this specification, above-mentioned L3 to L6 is same or different to each other, and is each independently direct key
The miscellaneous Asia of conjunction, the arlydene of substituted or unsubstituted carbon atom number 6 to 60 or substituted or unsubstituted carbon atom number 2 to 60
Aryl.
In an embodiment of this specification, above-mentioned L3 to L6 is same or different to each other, and is each independently direct key
The miscellaneous Asia of conjunction, the arlydene of substituted or unsubstituted carbon atom number 6 to 40 or substituted or unsubstituted carbon atom number 2 to 40
Aryl.
According to another embodiment, above-mentioned L3 to L6 is same or different to each other, be each independently Direct Bonding, replace or
It is unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted sub- terphenyl, substituted or unsubstituted
Naphthylene, substituted or unsubstituted anthrylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted triphenylene, substitution
Or unsubstituted fluorenyl, substituted or unsubstituted sub- thienyl, substituted or unsubstituted furylidene, substituted or unsubstituted two
Benzo Asia thienyl, substituted or unsubstituted dibenzo furylidene or substituted or unsubstituted sub- carbazyl.
In another embodiment, above-mentioned L3 to L6 is same or different to each other, and is each independently Direct Bonding, sub- benzene
It is base, biphenylene, sub- terphenyl, naphthylene, anthrylene, phenanthrylene, triphenylene, substituted or unsubstituted by methyl or phenyl
Fluorenyl, sub- thienyl, furylidene, dibenzo Asia thienyl, dibenzo furylidene or replaced by ethyl or phenyl or
Unsubstituted Asia carbazyl.
According to another embodiment, above-mentioned L3 to L6 is same or different to each other, and is each independently Direct Bonding or can be with
Selected from following structures.
According to an embodiment of this specification, L3 is Direct Bonding.
According to an embodiment of this specification, L4 is phenylene.
According to an embodiment of this specification, L5 and L6 are Direct Bonding.
In an embodiment of this specification, above-mentioned Ar2 to Ar5 is same or different to each other, and is each independently hydrogen, takes
The heteroaryl of the aryl or substituted or unsubstituted carbon atom number 2 to 60 of generation or unsubstituted carbon atom number 6 to 60.
According to another embodiment, above-mentioned Ar2 to Ar5 is same or different to each other, and is each independently hydrogen, by carbon atom number
The aryl of the substituted or unsubstituted carbon atom number 6 to 60 of heteroaryl of 6 to 60 aryl or carbon atom number 2 to 60 or by carbon
The heteroaryl of the aryl of atomicity 6 to 60 or the substituted or unsubstituted carbon atom number 2 to 60 of the heteroaryl of carbon atom number 2 to 60.
In another embodiment, above-mentioned Ar2 to Ar5 is same or different to each other, and is each independently hydrogen, replaces or do not take
The phenyl in generation, substituted or unsubstituted xenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted phenanthryl, substitution or not
Substituted anthryl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted naphthalene
And benzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazyl, substituted or unsubstituted fluorenes
Base, substituted or unsubstituted thienyl, substituted or unsubstituted furyl, substituted or unsubstituted benzothienyl, substitution or
Unsubstituted benzofuranyl, substituted or unsubstituted benzo fluorenyl, replaces or does not take substituted or unsubstituted benzo carbazole base
Indolocarbazole base, substituted or unsubstituted pyridyl group, substituted or unsubstituted isoquinolyl, the substituted or unsubstituted quinoline in generation
Quinoline base, substituted or unsubstituted triazine radical, substituted or unsubstituted benzimidazolyl, takes substituted or unsubstituted quinazolyl
Generation or unsubstituted benzoOxazolyl, substituted or unsubstituted acridan base, takes substituted or unsubstituted benzothiazolyl
Generation or unsubstituted xanthyl or substituted or unsubstituted dibenzo thiophene cough up base.
According to another embodiment, above-mentioned Ar2 to Ar5 is same or different to each other, and is each independently hydrogen, phenyl, biphenyl
Base is substituted with aryl or unsubstituted naphthalene, phenanthryl, anthryl, triphenylene, is substituted with aryl or unsubstituted dibenzofurans
Base, naphtho- benzofuranyl are substituted with aryl or unsubstituted dibenzothiophene, substituted or unsubstituted by alkyl or aryl
Carbazyl, by the substituted or unsubstituted fluorenyl of alkyl or aryl, be substituted with aryl or unsubstituted thienyl, be substituted with aryl or
Unsubstituted furyl, benzothienyl, benzofuranyl, by the substituted or unsubstituted benzo carbazole base of alkyl or aryl, quilt
Alkyl or aryl substituted or unsubstituted benzo fluorenyl, pyridyl group, is substituted with aryl or unsubstituted isoquinoline indolocarbazole base
Quinoline base, quinolyl are substituted with aryl or unsubstituted quinazolyl, are substituted with aryl or unsubstituted triazine radical, are taken by aryl
Generation or unsubstituted benzimidazolyl are substituted with aryl or unsubstituted benzoOxazolyl is substituted with aryl or unsubstituted benzene
Benzothiazolyl, by the substituted or unsubstituted acridan base of alkyl or aryl, by the substituted or unsubstituted xanthene of alkyl or aryl
Base or base is coughed up by the substituted or unsubstituted dibenzo thiophene of alkyl or aryl.
In another embodiment, above-mentioned Ar2 to Ar5 is same or different to each other, and is each independently hydrogen；Phenyl；Biphenyl
Base；It is substituted by phenyl or unsubstituted naphthalene；Phenanthryl；Anthryl；Triphenylene；It is substituted by phenyl or unsubstituted dibenzofurans
Base；Naphtho- benzofuranyl；It is substituted by phenyl or unsubstituted dibenzothiophene；Replaced by methyl, ethyl or phenyl or not
Substituted carbazyl；By the substituted or unsubstituted fluorenyl of methyl or phenyl；It is substituted by phenyl or unsubstituted thienyl；By phenyl
Substituted or unsubstituted furyl；Benzothienyl；Benzofuranyl；By the substituted or unsubstituted benzo carbazole of methyl or phenyl
Base；By the substituted or unsubstituted benzo fluorenyl of methyl or phenyl；Indolocarbazole base；It is substituted or unsubstituted by phenyl or naphthyl
Pyridyl group；It is substituted by phenyl or unsubstituted isoquinolyl；Quinolyl；It is substituted by phenyl or unsubstituted quinazolyl；By benzene
The substituted or unsubstituted triazine radical of base；It is substituted by phenyl or unsubstituted benzimidazolyl；It is substituted by phenyl or unsubstituted benzene
AndOxazolyl；It is substituted by phenyl or unsubstituted benzothiazolyl；By the substituted or unsubstituted acridan of methyl or phenyl
Base；By the substituted or unsubstituted xanthyl of methyl or phenyl；Or it is coughed up by the substituted or unsubstituted dibenzo thiophene of methyl or phenyl
Base.
In an embodiment of this specification, above-mentioned Ar2 to Ar5 is same or different to each other, be each independently hydrogen or
Selected from following structures.
According to an embodiment of this specification, above-mentioned organic matter layer includes luminescent layer, and above-mentioned luminescent layer includes by above-mentioned
The heterocyclic compound that chemical formula 1 indicates, above-mentioned luminescent layer also includes the compound indicated by following chemical formula 3.
[chemical formula 3]
In above-mentioned chemical formula 3,
R10 is hydrogen, deuterium, halogen group, itrile group, nitro, hydroxyl, aryloxy group, alkyl sulfenyl, artyl sulfo, alkyl sulfoxide
Base, aryl sulfoxid es base, silicyl, boryl, substituted or unsubstituted alkyl, substituted or unsubstituted naphthenic base, substitution or not
Substituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted aryl alkyl, substituted or unsubstituted alkyl amine group,
Substituted or unsubstituted aralkyl amido, substituted or unsubstituted heteroaryl amido, substituted or unsubstituted arylamine group, substitution
Or unsubstituted aryl heteroaryl amido, substituted or unsubstituted aryl phosphino- or substituted or unsubstituted heterocycle,
The integer that q is 0 to 7,
When q is 2 or more, the substituent group in bracket is same or different to each other,
L7 to L9 is same or different to each other, be each independently Direct Bonding or substituted or unsubstituted arlydene or
The substituted or unsubstituted heteroarylidene of person,
Ar6 to Ar8 is same or different to each other, and is each independently substituted or unsubstituted aryl or substitution or does not take
The heteroaryl in generation.
In an embodiment of this specification, above-mentioned R10 be hydrogen, deuterium, halogen group, silicyl, boryl, substitution or
Unsubstituted alkyl, substituted or unsubstituted naphthenic base, substituted or unsubstituted aryl, substituted or unsubstituted alkyl amine group,
Substituted or unsubstituted aralkyl amido, substituted or unsubstituted heteroaryl amido, substituted or unsubstituted arylamine group, substitution
Or unsubstituted aryl heteroaryl amido or substituted or unsubstituted heterocycle.
In an embodiment of this specification, above-mentioned R10 is same or different to each other, and is each independently hydrogen, deuterium, substitution
Or unsubstituted alkyl, substituted or unsubstituted naphthenic base, substituted or unsubstituted aryl or substituted or unsubstituted heterocycle
Base.
In an embodiment of this specification, above-mentioned R10 is same or different to each other, and is each independently hydrogen, deuterium, substitution
Or the alkyl of unsubstituted carbon atom number 1 to 50, substituted or unsubstituted carbon atom number 3 to 60 naphthenic base, replace or do not take
The heterocycle of the aryl of the carbon atom number 6 to 60 in generation or substituted or unsubstituted carbon atom number 2 to 40.
As soon as above-mentioned R10 is same or different to each other in the embodiment of this specification, it is each independently hydrogen, deuterium, takes
Generation or the alkyl of unsubstituted carbon atom number 1 to 30, substituted or unsubstituted carbon atom number 3 to 30 naphthenic base, replace or not
The heterocycle of the aryl of substituted carbon atom number 6 to 30 or substituted or unsubstituted carbon atom number 2 to 25.
In another embodiment, above-mentioned R10 is hydrogen.
In an embodiment of this specification, above-mentioned q is 0 or 1.
In an embodiment of this specification, above-mentioned L7 to L9 is same or different to each other, and is each independently direct key
The miscellaneous Asia of conjunction, the arlydene of substituted or unsubstituted carbon atom number 6 to 60 or substituted or unsubstituted carbon atom number 2 to 60
Aryl.
In an embodiment of this specification, above-mentioned L7 to L9 is same or different to each other, and is each independently direct key
The miscellaneous Asia of conjunction, the arlydene of substituted or unsubstituted carbon atom number 6 to 40 or substituted or unsubstituted carbon atom number 2 to 40
Aryl.
According to another embodiment, above-mentioned L7 to L9 is same or different to each other, be each independently Direct Bonding, replace or
It is unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted sub- terphenyl, substituted or unsubstituted
Naphthylene, substituted or unsubstituted anthrylene, substituted or unsubstituted phenanthrylene, substituted or unsubstituted triphenylene, substitution
Or unsubstituted fluorenyl, substituted or unsubstituted sub- thienyl, substituted or unsubstituted furylidene, substituted or unsubstituted two
Benzo Asia thienyl, substituted or unsubstituted dibenzo furylidene or substituted or unsubstituted sub- carbazyl.
In another embodiment, above-mentioned L7 to L9 is same or different to each other, and is each independently Direct Bonding, sub- benzene
It is base, biphenylene, sub- terphenyl, naphthylene, anthrylene, phenanthrylene, triphenylene, substituted or unsubstituted by methyl or phenyl
Fluorenyl, sub- thienyl, furylidene, dibenzo Asia thienyl, dibenzo furylidene or replaced by ethyl or phenyl or
Unsubstituted Asia carbazyl.
According to another embodiment, above-mentioned L7 to L9 is same or different to each other, and is each independently Direct Bonding or choosing
From following structures.
In an embodiment of this specification, above-mentioned L7 to L9 is Direct Bonding.
In an embodiment of this specification, above-mentioned Ar6 to Ar8 is same or different to each other, and is each independently substitution
Or unsubstituted carbon atom number 6 to 60 aryl or substituted or unsubstituted carbon atom number 2 to 60 heteroaryl.
According to another embodiment, above-mentioned Ar6 to Ar8 is same or different to each other, be each independently by carbon atom number 6 to
The aryl of the substituted or unsubstituted carbon atom number 6 to 60 of heteroaryl of 60 aryl or carbon atom number 2 to 60 or by carbon atom
The heteroaryl of the aryl of number 6 to 60 or the substituted or unsubstituted carbon atom number 2 to 60 of the heteroaryl of carbon atom number 2 to 60.
In another embodiment, above-mentioned Ar6 to Ar8 is same or different to each other, and is each independently substituted or unsubstituted
Phenyl, substituted or unsubstituted xenyl, substituted or unsubstituted naphthalene, substituted or unsubstituted phenanthryl, substitution or do not take
The anthryl in generation, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuran group, substituted or unsubstituted naphtho-
Benzofuranyl, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted carbazyl, substituted or unsubstituted fluorenes
Base, substituted or unsubstituted thienyl, substituted or unsubstituted furyl, substituted or unsubstituted benzothienyl, substitution or
Unsubstituted benzofuranyl, substituted or unsubstituted benzo fluorenyl, replaces or does not take substituted or unsubstituted benzo carbazole base
Indolocarbazole base, substituted or unsubstituted pyridyl group, substituted or unsubstituted isoquinolyl, the substituted or unsubstituted quinoline in generation
Quinoline base, substituted or unsubstituted triazine radical, substituted or unsubstituted benzimidazolyl, takes substituted or unsubstituted quinazolyl
Generation or unsubstituted benzoOxazolyl, substituted or unsubstituted acridan base, takes substituted or unsubstituted benzothiazolyl
Generation or unsubstituted xanthyl or substituted or unsubstituted dibenzo thiophene cough up base.
According to another embodiment, above-mentioned Ar6 to Ar8 is same or different to each other, be each independently phenyl, xenyl,
Be substituted with aryl or unsubstituted naphthalene, phenanthryl, anthryl, triphenylene, be substituted with aryl or unsubstituted dibenzofuran group,
Naphtho- benzofuranyl, be substituted with aryl or unsubstituted dibenzothiophene, by the substituted or unsubstituted click of alkyl or aryl
Oxazolyl, by the substituted or unsubstituted fluorenyl of alkyl or aryl, be substituted with aryl or unsubstituted thienyl, be substituted with aryl or not
Substituted furyl, benzothienyl, benzofuranyl, by the substituted or unsubstituted benzo carbazole base of alkyl or aryl, by alkane
Base or aryl substituted or unsubstituted benzo fluorenyl, pyridyl group, are substituted with aryl or unsubstituted isoquinolin indolocarbazole base
Base, quinolyl are substituted with aryl or unsubstituted quinazolyl, are substituted with aryl or unsubstituted triazine radical, are substituted with aryl
Or it unsubstituted benzimidazolyl, is substituted with aryl or unsubstituted benzoOxazolyl is substituted with aryl or unsubstituted benzo
Thiazolyl, by the substituted or unsubstituted acridan base of alkyl or aryl, by the substituted or unsubstituted xanthyl of alkyl or aryl,
Or base is coughed up by the substituted or unsubstituted dibenzo thiophene of alkyl or aryl.
In another embodiment, above-mentioned Ar6 to Ar8 is same or different to each other, and is each independently phenyl；Xenyl；
It is substituted by phenyl or unsubstituted naphthalene；Phenanthryl；Anthryl；Triphenylene；It is substituted by phenyl or unsubstituted dibenzofuran group；
Naphtho- benzofuranyl；It is substituted by phenyl or unsubstituted dibenzothiophene；It is substituted or unsubstituted by methyl, ethyl or phenyl
Carbazyl；By the substituted or unsubstituted fluorenyl of methyl or phenyl；It is substituted by phenyl or unsubstituted thienyl；It is substituted by phenyl
Or unsubstituted furyl；Benzothienyl；Benzofuranyl；By the substituted or unsubstituted benzo carbazole base of methyl or phenyl；
By the substituted or unsubstituted benzo fluorenyl of methyl or phenyl；Indolocarbazole base；By the substituted or unsubstituted pyrrole of phenyl or naphthyl
Piperidinyl；It is substituted by phenyl or unsubstituted isoquinolyl；Quinolyl；It is substituted by phenyl or unsubstituted quinazolyl；By phenyl
Substituted or unsubstituted triazine radical；It is substituted by phenyl or unsubstituted benzimidazolyl；It is substituted by phenyl or unsubstituted benzoOxazolyl；It is substituted by phenyl or unsubstituted benzothiazolyl；By the substituted or unsubstituted acridan base of methyl or phenyl；
By the substituted or unsubstituted xanthyl of methyl or phenyl；Or base is coughed up by the substituted or unsubstituted dibenzo thiophene of methyl or phenyl.
In an embodiment of this specification, above-mentioned Ar6 to Ar8 is same or different to each other, and is each independently selected from down
State structure.
According to an embodiment of this specification, above-mentioned organic matter layer includes luminescent layer, and above-mentioned luminescent layer includes by above-mentioned
Material of main part of the heterocyclic compound that chemical formula 1 indicates as luminescent layer.
According to an embodiment of this specification, above-mentioned organic matter layer includes luminescent layer, and above-mentioned luminescent layer includes by above-mentioned
Dopant of the heterocyclic compound that chemical formula 1 indicates as luminescent layer.
According to an embodiment of this specification, above-mentioned organic matter layer includes luminescent layer, and above-mentioned luminescent layer includes by above-mentioned
Dopant of the heterocyclic compound that chemical formula 1 indicates as luminescent layer, includes the change indicated by above-mentioned chemical formula 2 or chemical formula 3
Close material of main part of the object as luminescent layer.
According to an embodiment of this specification, above-mentioned organic matter layer includes luminescent layer, and above-mentioned luminescent layer includes by above-mentioned
Dopant of the heterocyclic compound that chemical formula 1 indicates as luminescent layer, includes the change indicated by above-mentioned chemical formula 2 or chemical formula 3
Material of main part of the object as luminescent layer is closed, the heterocyclic compound indicated by above-mentioned chemical formula 1 can be mixed with 2 to 10wt%
It is miscellaneous.
According to an embodiment of this specification, above-mentioned organic matter layer includes hole blocking layer, electron transfer layer or electronics
Implanted layer, above-mentioned hole blocking layer, electron transfer layer or electron injecting layer include the heterocyclic compound indicated by above-mentioned chemical formula 1
Object.
According to an embodiment of this specification, above-mentioned organic matter layer can also be comprising passing selected from hole injection layer, hole
1 layer or more in defeated layer, luminescent layer, electron transfer layer and electron injecting layer.
Organic illuminating element according to an embodiment of this specification includes: first electrode, second electrode and having
Luminescent layer between above-mentioned first electrode and above-mentioned second electrode, above-mentioned luminescent layer include to indicate miscellaneous by above-mentioned chemical formula 1
Cycle compound.
According to another embodiment, organic illuminating element of the invention includes: first electrode, second electrode and having
Luminescent layer between above-mentioned first electrode and above-mentioned second electrode, above-mentioned luminescent layer include to indicate miscellaneous by above-mentioned chemical formula 1
Cycle compound can also include material of main part as dopant.
In another embodiment, organic illuminating element of the invention includes: first electrode, second electrode and having
Luminescent layer between above-mentioned first electrode and above-mentioned second electrode, above-mentioned luminescent layer include to indicate miscellaneous by above-mentioned chemical formula 1
Cycle compound can also include material of main part as dopant, and aforementioned body material can be for by the expression of above-mentioned chemical formula 2 or 3
Compound.Above-mentioned organic illuminating element other than luminescent layer, can also comprising selected from hole transmission layer, hole injection layer,
1 or more organic matter layer in electron transfer layer and electron injecting layer.But it the structure of organic illuminating element but does not limit
In this.
According to another embodiment, organic illuminating element of the invention includes: first electrode, second electrode and having
Luminescent layer between above-mentioned first electrode and second electrode may include between above-mentioned first electrode and luminescent layer selected from hole
1 or more organic matter layer in implanted layer and hole transmission layer, may include choosing between above-mentioned second electrode and luminescent layer
From 1 or more organic matter layer in electron transfer layer and electron injecting layer.But the structure of organic illuminating element of the invention
But not limited to this.
In another embodiment, organic illuminating element of the invention includes: first electrode, second electrode and having
Luminescent layer between above-mentioned first electrode and second electrode, above-mentioned luminescent layer include the jeterocyclic chemistry indicated by above-mentioned chemical formula 1
Object is closed as material of main part, may include in hole injection layer and hole transmission layer between above-mentioned first electrode and luminescent layer
1 or more organic matter layer, may include between above-mentioned second electrode and luminescent layer selected from electron transfer layer and electronics note
Enter 1 or more organic matter layer in layer.But but not limited to this for the structure of organic illuminating element of the invention.
According to another embodiment, organic illuminating element of the invention includes: first electrode, second electrode and having
Luminescent layer between above-mentioned first electrode and second electrode, above-mentioned luminescent layer include the jeterocyclic chemistry indicated by above-mentioned chemical formula 1
Object is closed as dopant, the material of main part comprising the compound that is indicated by above-mentioned chemical formula 2 or 3 as luminescent layer, above-mentioned the
It may include 1 or more the organic matter layer in hole injection layer and hole transmission layer between one electrode and luminescent layer,
It may include 1 or more the organic matter in electron transfer layer and electron injecting layer between above-mentioned second electrode and luminescent layer
Layer.But but not limited to this for the structure of organic illuminating element of the invention.
In the organic illuminating element of this specification, 1 layer or more in organic matter layer include this specification heterocyclic compound,
The heterocyclic compound indicated by above-mentioned chemical formula 1 can pass through material and method system well known to the technical field in addition to this
It makes.
When above-mentioned organic illuminating element includes multiple organic matter layers, above-mentioned organic matter layer can be by same substance or difference
Substance is formed.
For example, the organic illuminating element of this specification can be by stacking gradually first electrode, organic matter layer on substrate
And second electrode and manufacture.At this point it is possible to manufacture as follows: using such as sputtering method (sputtering) or electron beam
The physical vapor depositions methods such as evaporation (e-beam evaporation) (PVD:physical Vapor Deposition) are in substrate
Upper evaporation metal or conductive metal oxide or their alloy and form first electrode, then in the first electrode
It is upper to form the organic matter layer comprising hole injection layer, hole transmission layer, luminescent layer and electron transfer layer, later in the organic matter
Vapor deposition can be used as the substance of second electrode on layer.In addition to the method described above, second electrode can also successively be deposited on substrate
Substance, organic matter layer substance, first electrode substance manufacture organic illuminating element.In addition, about being indicated by above-mentioned chemical formula 1
Heterocyclic compound not only can use vacuum vapour deposition when manufacturing organic illuminating element, can also using solution coating method come
Form organic matter layer.Herein, so-called solution coating method refers to spin-coating method, dip coating, knife coating, ink jet printing method, silk-screen printing
Method, spray-on process, rolling method etc., but not limited to this.
According to an embodiment of this specification, above-mentioned first electrode is anode, and above-mentioned second electrode is cathode.
According to another embodiment of this specification, above-mentioned first electrode is cathode, and above-mentioned second electrode is anode.
As above-mentioned anode material, generally for enabling hole successfully to inject to organic matter layer, preferably work function
Big substance.As the specific example for the anode material that can be used in the present invention, just like metals such as vanadium, chromium, copper, zinc, gold or
Their alloy；Such as zinc oxide, indium oxide, tin indium oxide (ITO), indium zinc oxide (IZO) metal oxide；Such as ZnO:Al or
SnO2: the combination of the metals such as Sb and oxide；Such as poly- (3 methyl thiophene), poly- [3,4- (ethylidene -1,2- dioxy) thiophene]
(PEDOT), electroconductive polymers such as polypyrrole and polyaniline etc., but not limited to this.
As above-mentioned cathode substance, generally for electronics is easily injected into organic matter layer, preferably work function is small
Substance.It is golden just like magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminium, silver, tin and lead etc. as the specific example of cathode substance
Category or their alloy；Such as LiF/Al or LiO2Multilayered structures substance such as/Al, Mg/Ag etc., but not limited to this.
Above-mentioned hole injection layer is the layer in the hole that injection carrys out self-electrode, as hole injecting material, preferably followingization
Close object: the ability with transporting holes has hole injection effect from anode, for the excellent of luminescent layer or luminescent material
Hole inject effect, prevent the exciton generated in luminescent layer from migrating to electron injecting layer or electron injection material, and film
Forming ability is excellent.It is preferred that HOMO (highest occupied molecular orbital(HOMO), the highest occupied of hole injecting material
Molecular orbital) between the work function of anode material and the HOMO of surrounding organic matter layer.As hole infusion
The concrete example of matter has metalloporphyrin (porphyrin), Oligopoly thiophene, aryl amine system organic matter, six nitriles, six azepine benzophenanthrene system to have
It is organic matter, anthraquinone and polyaniline and polythiophene that machine object, quinacridone (quinacridone), which are organic matter, (perylene),
It is electroconductive polymer etc., but not limited to this.
Above-mentioned hole transmission layer is to receive the hole from hole injection layer and by the layer of hole transport to luminescent layer, as
Hole transporting material is the substance that can be received the hole from anode or hole injection layer and transfer them to luminescent layer, empty
Mobility big substance in cave is suitable.As concrete example, there are aryl amine system organic matter, electroconductive polymer and deposit simultaneously
In conjugate moiety and the block copolymer of non-conjugated portion etc., but not limited to this.
It is that can receive the sky from hole transmission layer and electron transfer layer respectively as the luminescent substance of above-mentioned luminescent layer
Cave and electronics and make they in conjunction with and issue the substance of the light of visible light region, the preferably quantum efficiency for fluorescence or phosphorescence
High substance.As a specific example, there is 8-hydroxyquinoline aluminum complex (Alq3)；Carbazole based compound；Two is polystyrene-based
(dimerized styryl) compound；BAlq；10- hydroxy benzo quinoline metal compound；BenzoAzoles, benzothiazole and
Benzimidazole based compound；Poly- (to phenyleneethenyl) (PPV) is macromolecule；Loop coil (spiro) compound；It is polyfluorene, red glimmering
Alkene etc., but not limited to this.
Above-mentioned luminescent layer may include material of main part and dopant material.As material of main part, there is aromatic fused ring derivative
Object or nitrogen-containing heterocgcies etc..Specifically, having anthracene derivant, pyrene derivatives, naphthalene derivative as aromatic fused ring derivative
Object, pentacene derivative, phenanthrene compound, fluoranthene compound etc. have carbazole derivates, dibenzo furan as nitrogen-containing heterocgcies
It mutters derivative, ladder type furan compoundAnd pyrimidine derivatives etc., but be not limited to
This.
As above-mentioned dopant material, there are aromatic amine derivative, styrylamine compound, boron complexes, fluoranthene chemical combination
Object, metal complex etc..Specifically, being the virtue with substituted or unsubstituted arylamino as aromatic amine derivative
Fragrant race's fused-ring derivatives, have pyrene with arylamino, anthracene,Two indeno pyrenes (Periflanthene) etc., as styrene
Ylamine compounds are to replace the compound for having at least one aryl vinyl on substituted or unsubstituted arylamine, are selected from
More than one substituent group in aryl, silicyl, alkyl, naphthenic base and arylamino is substituted or unsubstituted.It is specific and
Speech, has styryl amine, styryl diamines, styryl triamine, styryl tetramine etc., but not limited to this.In addition,
As metal complex, there are complex of iridium, platinum complex etc., but not limited to this.
Above-mentioned electron transfer layer is from electron injecting layer reception electronics and by the layer of electron-transport to luminescent layer, as electronics
Transport materials are can to receive well electronics from cathode and transfer them to the substance of luminescent layer, the big object of electron mobility
Matter is suitable.As concrete example, there is the Al complex of 8-hydroxyquinoline, comprising Alq3Complex, organic free radical chemical combination
Object, flavonol-metal complex etc., but not limited to this.Electron transfer layer can as used in the prior art that
Sample and the cathode substance of any desired are used together.In particular, the example of suitable cathode substance is with low work function and companion
There is the common substance of aluminium layer or silver layer.Specially caesium, barium, calcium, ytterbium and samarium, for above-mentioned each substance, with aluminium layer
Or silver layer.
Above-mentioned electron injecting layer is the layer for the electronics that injection carrys out self-electrode, preferably following compound: has transmission electronics
Ability, there is electron injection effect from cathode, for the excellent electron injection effect of luminescent layer or luminescent material, prevent
Only generated exciton is migrated to hole injection layer in luminescent layer, and film-forming energy is excellent.Specifically, have Fluorenone,
Anthraquinone bismethane (Anthraquinodimethane), diphenoquinone, thiopyrandioxide,Azoles,Diazole, triazole, imidazoles,
Tetrabasic carboxylic acid, fluorenylidene-methane, anthrone etc. and their derivative, metal complex compounds and nitrogenous five-membered ring derivative
Deng but not limited to this.
As above-mentioned metal complex, there are 8-hydroxyquinoline lithium, bis- (8-hydroxyquinoline) zinc, bis- (8-hydroxyquinolines)
Copper, bis- (8-hydroxyquinoline) manganese, three (8-hydroxyquinoline) aluminium, three (2- methyl -8-hydroxyquinoline) aluminium, three (8-hydroxyquinolines)
Gallium, bis- (10- hydroxy benzo [h] quinoline) berylliums, bis- (10- hydroxy benzo [h] quinoline) zinc, bis- (2- methyl -8- quinoline) gallium chlorides,
Bis- (2- methyl -8- quinoline) (o-cresol) galliums, bis- (2- methyl -8- quinoline) (1- naphthols) aluminium, bis- (2- methyl -8- quinoline) (2-
Naphthols) gallium etc., but not limited to this.
Organic illuminating element involved in this specification can be sent out according to used material for top emission type, bottom
Light type or bidirectional luminescence type.
In the following, enumerating embodiment in order to which this specification is concretely demonstrated and being described in detail.However, this theory
Embodiment involved in bright book can be deformed into other various forms, should not be construed to this specification range be limited at it is following
The embodiment of detailed description.The embodiment of this specification is mentioned to be more fully explained this specification to those skilled in the art
It supplies.
<synthesis example>
The synthesis of 1. intermediate 1-a of synthesis example
According to following 1 synthetic intermediate 1-a of reaction equation.
<reaction equation 1>
The bromo- 5- chlorobenzaldehyde (20.0g, 74mmol) of 2-, 4- dibenzofurans ylboronic acid (17.3g, 82mmol) is complete
After being dissolved in the tetrahydrofuran of 300mL, potassium carbonate (30.7g, 222mmol) aqueous solution of 100mL is added, adds four (triphenyls
Phosphine) after palladium (0.86g, 0.74mmol), return stirring 24 hours.After reaction, room temperature is cooled the temperature to, water and second are then used
Acetoacetic ester is extracted and separates organic layer.After organic layer is handled with anhydrous magnesium sulfate, filtering is concentrated under reduced pressure.Solid acetic acid second
Ester recrystallization obtains<intermediate 1-a>(21.7g, 82%).
MS [M+]=356.06
The synthesis of 2. intermediate 1-b of synthesis example
According to following 2 synthetic intermediate 1-b of reaction equation.
<reaction equation 2>
After<intermediate 1-a>(20.0g, 56mmol) is dissolved in the tetrahydrofuran of 300mL, by sodium hypochlorite (5.6g,
62mmol), sulfamic acid (8.2g, 84mmol) is diluted with water (each 50mL) and is added, heating stirring 4 hours.After reaction,
After cooling the temperature to room temperature, is extracted with water and ethyl acetate and separate organic layer.After organic layer is handled with anhydrous magnesium sulfate, filtering
It is concentrated under reduced pressure.Solid ethyl acetate and hexane recrystallization have obtained<intermediate 1-b>(18.8g, 90%).
MS [M+]=372.80
The synthesis of 3. intermediate 1-c of synthesis example
According to following 3 synthetic intermediate 1-c of reaction equation.
<reaction equation 3>
Be added<intermediate 1-b>(18.0g, 48mmol), 250mL methanesulfonic acid, with 80 DEG C heating stirring 9 hours.Reaction
After, it after cooling the temperature to room temperature, is slowly added drop-wise in water, generates solid.The solid water and ethanol washing of generation and obtain
<intermediate 1-c>(16.2g, 95%) is arrived.
MS [M+]=354.79
The synthesis of 4. intermediate 1-d of synthesis example
According to following 4 synthetic intermediate 1-d of reaction equation.
<reaction equation 4>
After<intermediate 1-c>(10.0g, 28.1mmol) is added in the methylene chloride of 300mL and is stirred, slowly it is added dropwise
In the methylene chloride of 50mL after diluted bromine (6.76g, 42.3mmol), at stirring at normal temperature 48 hours.Then, consolidating generation
Body is filtered, and is washed with methylene chloride and hexane.Solid toluene and hexane recrystallization obtain<intermediate 1-d>
(7.92g, 65%).
MS [M+]=433.69
The synthesis of 5. intermediate 1-e of synthesis example
According to following 5 synthetic intermediate 1-e of reaction equation.
<reaction equation 5>
Under nitrogen atmosphere, the tetrahydrofuran of 9- (2- bromophenyl) -9H- carbazole (6.13g, 19.0mmol) and 150mL is added, it is cold
But to -78 DEG C.In cooling reaction solution, after n-BuLi (7.60mL, 19.0mmol) is added dropwise, stir 1 hour.Then,
It is added<intermediate 1-d>(7.50g, 17.3mmol), in stirring at normal temperature.After reaction, saturated sodium bicarbonate is added to terminate
After reaction, extracted with ethyl acetate and water.After organic layer is handled with anhydrous magnesium sulfate, filtering is concentrated under reduced pressure.Solid acetic acid second
Ester and hexane recrystallization obtain<intermediate 1-e>(8.31g, 71%).
The synthesis of 6. intermediate 1-f of synthesis example
According to following 6 synthetic intermediate 1-f of reaction equation.
<reaction equation 6>
2 drop sulfuric acid are added in<intermediate 1-e>(8.00g, 11.8mmol) and acetic acid (100mL), heating stirring 3 is small
When.After reaction, after crossing filter solid, with water and ethanol washing, then obtained with ethyl acetate and hexane recrystallization < in
Mesosome 1-f > (7.40g, 95%).
MS [M+]=658.98
The synthesis of 7. compound 1 of synthesis example
Compound 1 is synthesized according to following reaction equations 7.
<reaction equation 7>
Under nitrogen atmosphere, in round-bottomed flask, by<intermediate 1-f>(6.0g, 9.10mmol), bis- (4- tert-butyl-phenyl) amine
(5.63g, 20.0mmol), sodium tert-butoxide (4.37g, 45.5mmol), bis- (three-tert-butyl phosphines) palladiums (0) (0.23g,
It 0.46mmol) is added in the toluene of 80mL, return stirring.At the end of reaction, after being cooled to room temperature, extracted with toluene and water,
Remove water layer.After being handled with anhydrous magnesium sulfate, filtering is concentrated under reduced pressure.Product uses column chromatography after purification, with toluene and oneself
Alkane recrystallization obtains<compound 1>(6.03g, 60%).
MS [M+]=1104.5
The synthesis of 8. compound 2,10 and 11 of synthesis example
Utilize<intermediate 1-f>, 4- tert-butyl-phenyl -4- trimethylsilylphenyl amine, di-o-tolyl amine2- fluorine o-tolyl amine (2- ), according to
Synthesis example 7 is respectively synthesized compound 2 and 10 and 11.
Compound 2；MS [M+]=1136.6, compound 10；MS [M+]=936.1, compound 11；MS [M+]=944.1
The synthesis of 9. intermediate 3-a of synthesis example
Using 1- dibenzofurans ylboronic acid,<intermediate 3-a>is synthesized according to synthesis example 1.
MS [M+]=356.06
The synthesis of 10. intermediate 3-f of synthesis example
It utilizes<intermediate 3-a>,<intermediate 3-f>is synthesized according to synthesis example 2 to 6.
MS [M+]=658.98
The synthesis of 11. compound 3,4,6 and 7 of synthesis example
Utilize<intermediate 3-f>, 4- tert-butyl-phenyl -9- dimethyl fluorenamine, 4- tert-butyl-phenyl -4- dibenzofurans
Amine, 4- tert-butyl-phenyl -2- naphthylamines, 4- tert-butyl-phenyl-naphthalidine, are respectively synthesized compound 3,4,6 and 7 according to synthesis example 7.
Compound 3；MS [M+]=1224.6, compound 4；MS [M+]=1172.4, compound 6；MS [M+]=1092.4,
Compound 7；MS [M+]=1092.4
The synthesis of 12. intermediate 5-a of synthesis example
Using 1- dimethyl fluorene boric acid,<intermediate 5-a>is synthesized according to synthesis example 1.
MS [M+]=398.96
The synthesis of 13. intermediate 5-f of synthesis example
It utilizes<intermediate 5-a>,<intermediate 5-f>is synthesized according to synthesis example 2 to 6.
MS [M+]=701.14
The synthesis of 14. compound 5 of synthesis example
<intermediate 5-f>and double -4- tert-butylamines are utilized, compound 5 is synthesized according to synthesis example 7.
Compound 5；MS [M+]=1146.6
The synthesis of 15. intermediate 8-a of synthesis example
Using 4- naphtho- benzofuran boronic acids,<intermediate 8-a>is synthesized according to synthesis example 1.
MS [M+]=406.87
The synthesis of 16. intermediate 8-f of synthesis example
It utilizes<intermediate 8-a>,<intermediate 8-f>is synthesized according to synthesis example 2 to 6.
MS [M+]=709.04
The synthesis of 17. compound 8 of synthesis example
<intermediate 8-f>and double -4- tert-butyl-phenyl amine are utilized, compound 8 is synthesized according to synthesis example 8.
Compound 8；MS [M+]=1154.5
The synthesis of 18. intermediate 9-a of synthesis example
Using 4- dibenzothiophenes boric acid,<intermediate 9-a>is synthesized according to synthesis example 1.
MS [M+]=372.87
The synthesis of 19. intermediate 9-f of synthesis example
It utilizes<intermediate 9-a>,<intermediate 9-f>is synthesized according to synthesis example 2 to 6.
MS [M+]=675.04
The synthesis of 20. compound 9 of synthesis example
<intermediate 9-f>and 4- tert-butyl-phenyl -1- phenyl amine are utilized, compound 9 is synthesized according to synthesis example 7.
Compound 9；MS [M+]=1008.3
<embodiment>
Embodiment 1.
It will be withThickness thin film be coated with the glass substrate of ITO (tin indium oxide, indium tin oxide)
(healthy and free from worry 7059 glass) is put into the distilled water dissolved with dispersing agent, is washed using ultrasonic wave.At this moment, detergent uses luxuriant and rich with fragrance
Xi Er company (Fischer Co.) product, distilled water use the filter manufactured by Millipore Corp. (Millipore Co.)
(Filter) 2 distilled water is filtered.After ITO is washed 30 minutes, it is repeated twice with distilled water and carries out 10 minutes ultrasonic waves
Washing.After distilling water washing, ultrasonic washing is successively carried out with the solvent of isopropyl alcohol, acetone and methanol and is done
It is dry.
On the ito transparent electrode prepared in this way, withThickness thermal vacuum above-mentioned HAT is deposited and forms hole note
Enter layer.Over the hole-injecting layer, as hole transmission layer, vacuum evaporationAbove-mentioned HT-A, then withIt is thick
Degree vapor deposition HT-B.On the light-emitting layer, as material of main part, H-A and compound 1 are doped with 2~10wt%, with
Thickness vacuum evaporation.Then, with film thicknessBy ET-A and Liq with 1:1 ratio vapor deposition, successively it is deposited above itThe magnesium (Mg) of the silver (Ag) doped with 10wt% of thickness andThe aluminium of thickness and form cathode, to manufacture
Organic illuminating element.
In above process, the evaporation rate of organic matter maintainsLiF is maintainedEvaporation rate,
Aluminium maintainsExtremelyEvaporation rate.
Embodiment 2.
In above-described embodiment 1, pass through side same as Example 1 in addition to this instead of compound 1 using compound 3
Legal system makes organic illuminating element.
Embodiment 3.
In above-described embodiment 1, pass through side same as Example 1 in addition to this instead of compound 1 using compound 4
Legal system makes organic illuminating element.
Embodiment 4.
In above-described embodiment 1, pass through side same as Example 1 in addition to this instead of compound 1 using compound 7
Legal system makes organic illuminating element.
Embodiment 5.
In above-described embodiment 1, compound 1 is replaced using compound 10, in addition to this, by same as Example 1
Method manufactures organic illuminating element.
Embodiment 6.
In above-described embodiment 1, compound 1 is replaced using compound 11, in addition to this, by same as Example 1
Method manufactures organic illuminating element.
Embodiment 7.
In above-described embodiment 1, material of main part H-A is replaced to pass through side same as Example 1 in addition to this using H-B
Legal system makes organic illuminating element.
Embodiment 8.
In above-described embodiment 7, pass through side same as Example 7 in addition to this instead of compound 1 using compound 3
Legal system makes organic illuminating element.
Embodiment 9.
In above-described embodiment 7, pass through side same as Example 7 in addition to this instead of compound 1 using compound 4
Legal system makes organic illuminating element.
Embodiment 10.
In above-described embodiment 7, pass through side same as Example 7 in addition to this instead of compound 1 using compound 7
Legal system makes organic illuminating element.
Embodiment 11.
In above-described embodiment 7, compound 1 is replaced using compound 10, in addition to this, by same as Example 7
Method manufactures organic illuminating element.
Embodiment 12.
In above-described embodiment 7, compound 1 is replaced using compound 11, in addition to this, by same as Example 7
Method manufactures organic illuminating element.
Embodiment 13.
In above-described embodiment 1, H-A is replaced using material of main part H-C, in addition to this, by identical with embodiment 13
Method manufactures organic illuminating element.
Embodiment 14.
In above-described embodiment 13, compound 1 is replaced using compound 3, in addition to this, by identical with embodiment 13
Method manufactures organic illuminating element.
Embodiment 15.
In above-described embodiment 13, compound 1 is replaced using compound 4, in addition to this, by identical with embodiment 13
Method manufactures organic illuminating element.
Embodiment 16.
In above-described embodiment 13, compound 1 is replaced using compound 7, in addition to this, by identical with embodiment 13
Method manufactures organic illuminating element.
Embodiment 17.
In above-described embodiment 13, compound 1 is replaced using compound 10, in addition to this, by identical as embodiment 13
Method manufacture organic illuminating element.
Embodiment 18.
In above-described embodiment 13, compound 1 is replaced using compound 11, in addition to this, by identical as embodiment 13
Method manufacture organic illuminating element.
<comparative example>
Comparative example 1.
In above-described embodiment 1, compound 1 is replaced to pass through method system same as Example 1 in addition to this using D-1
Make organic illuminating element.
Comparative example 2.
In above-described embodiment 1, compound 1 is replaced to pass through method system same as Example 1 in addition to this using D-2
Make organic illuminating element.
Comparative example 3.
In above-described embodiment 1, compound 1 is replaced to pass through method system same as Example 1 in addition to this using D-3
Make organic illuminating element.
Comparative example 4.
In above-described embodiment 7, compound 1 is replaced to pass through method system same as Example 7 in addition to this using D-1
Make organic illuminating element.
Comparative example 5.
In above-described embodiment 7, compound 1 is replaced to pass through method system same as Example 7 in addition to this using D-2
Make organic illuminating element.
Comparative example 6.
In above-described embodiment 7, compound 1 is replaced to pass through method system same as Example 7 in addition to this using D-3
Make organic illuminating element.
Comparative example 7.
In above-described embodiment 13, compound 1 is replaced to pass through method identical with embodiment 13 in addition to this using D-1
Manufacture organic illuminating element.
Comparative example 8.
In above-described embodiment 13, compound 1 is replaced to pass through method identical with embodiment 13 in addition to this using D-2
Manufacture organic illuminating element.
Comparative example 9.
In above-described embodiment 13, compound 1 is replaced to pass through method identical with embodiment 13 in addition to this using D-3
Manufacture organic illuminating element.
By the organic illuminating element of above-described embodiment 1 to 18 and comparative example 1 to comparative example 9 10mA/cm current density
Driving voltage and luminous efficiency are measured, the required time when the current density measurement original intensity of 20mA/cm is decreased to 95%
(LT95).It the results are shown in following table 1.
[table 1]
The embodiment 1 to 18 and comparative example 1 to 9 of more above-mentioned table 1, in the jeterocyclic chemistry comprising being indicated by above-mentioned chemical formula 1
In the case where closing object and the organic illuminating element that manufactures, prevent from dividing caused by the accumulation of intermolecular densification due to three-dimensional structure
Fluorescence decay between son, to show excellent performance.Moreover, in the state of losing an electronics (cationic condition,
Cation condition), the electron density distribution of HOMO is typically distributed across known includes with stable cationic state
The spiral shell indoles and acridine moiety of nitrogen, to bring the improvement of component life.Thus it is confirmed that with pyrene system or fluorenes system chemical combination is included
The organic illuminating element manufactured in the comparative example 1 to 9 of object is compared, and efficiency and life characteristic are excellent.
Claims (17)
1. a kind of heterocyclic compound indicated by following chemical formula 1:
Chemical formula 1
In the chemical formula 1,
R5 to R8 is same or different to each other, and is each independently hydrogen, deuterium, halogen group, itrile group, nitro, hydroxyl, aryloxy group, alkane
Base sulfenyl, artyl sulfo, alkyl sulfoxide base, aryl sulfoxid es base, silicyl, boryl, substituted or unsubstituted alkyl, substitution or
Unsubstituted naphthenic base, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted aryl alkyl,
Substituted or unsubstituted alkyl amine group, substituted or unsubstituted heteroaryl amido, replaces substituted or unsubstituted aralkyl amido
Or it unsubstituted arylamine group, substituted or unsubstituted aryl heteroaryl amido, substituted or unsubstituted aryl phosphino- or takes
Generation or unsubstituted heterocycle,
L1 and L2 are same or different to each other, be each independently Direct Bonding, substituted or unsubstituted arlydene or substitution or
The heterocycle of unsubstituted divalent,
Ar1 is substituted or unsubstituted heterocycle,
R1 to R4 is same or different to each other, and is each independently substituted or unsubstituted aryl or substituted or unsubstituted miscellaneous
Ring group,
A and b is respectively 0 to 4 integer,
The integer that c is 0 to 3,
The integer that d is 0 to 5,
When a to d is respectively 2 or more, the substituent group in bracket is same or different to each other,
N1 and n2 is 0 or 1,
1 in n1 and n2 the above are 1 integer,
X1 and X2 is hydrogen or is bonded directly with one another.
2. heterocyclic compound according to claim 1, wherein Ar1-L2-NR3R4 is one of following structures:
Defining for L2, R3 and R4 is identical as the definition in the chemical formula 1,
R' and R " are same or different to each other, and are each independently hydrogen, deuterium, halogen group, itrile group, nitro, hydroxyl, aryloxy group, alkane
Base sulfenyl, artyl sulfo, alkyl sulfoxide base, aryl sulfoxid es base, silicyl, boryl, substituted or unsubstituted alkyl, substitution or
Unsubstituted naphthenic base, substituted or unsubstituted alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted aryl alkyl,
Substituted or unsubstituted alkyl amine group, substituted or unsubstituted heteroaryl amido, replaces substituted or unsubstituted aralkyl amido
Or it unsubstituted arylamine group, substituted or unsubstituted aryl heteroaryl amido, substituted or unsubstituted aryl phosphino- or takes
Generation or unsubstituted heterocycle,
The structure can be further substituted.
3. heterocyclic compound according to claim 1, wherein L1 and L2 are same or different to each other, and are each independently straight
Connect the 2 of bonding, the arlydene of substituted or unsubstituted carbon atom number 6 to 30 or substituted or unsubstituted carbon atom number 2 to 30
The heterocycle of valence.
4. heterocyclic compound according to claim 1, wherein L1 and L2 are same or different to each other, and are each independently straight
Connect one of bonding or following structures:
5. heterocyclic compound according to claim 1, wherein R1 to R4 is same or different to each other, and is each independently and takes
The heterocycle of the aryl or substituted or unsubstituted carbon atom number 2 to 30 of generation or unsubstituted carbon atom number 6 to 30.
6. heterocyclic compound according to claim 1, wherein R1 to R4 is same or different to each other, and is each independently down
State one of structure:
In the structure,
R201 to R297 is same or different to each other, and is each independently hydrogen, deuterium, halogen group, itrile group, nitro, silicyl, boron
It is base, substituted or unsubstituted amido, substituted or unsubstituted alkyl, substituted or unsubstituted naphthenic base, substituted or unsubstituted
Aryl or substituted or unsubstituted heteroaryl,
A1, a6, a10, a23 and a25 are respectively 0 to 5 integer,
A2, a5, a8, a9, a14, a16, a17, a21, a28 are to a35, b1 to b4, b6 to b9, b11 to b13, b15 and b17 to b32
Respectively 0 to 4 integer,
A3 and a22 is respectively 0 to 7 integer,
A4, a7, a12, a15, a19, a26 and a27 are respectively 0 to 3 integer,
The integer that a11 is 0 to 9,
A13, a20 and a24 are respectively 0 to 6 integer,
A18, b5, b10, b14 and b16 are respectively 0 to 2 integer,
When a18, b5, b10, b14 and b16 are 2, the substituent group in bracket is different from each other,
A1, a6, a10, a23, a25, a2, a5, a8, a9, a14, a16, a17, a21, a28 are to a35, b1 to b4, b6 to b9, b11
To b13, b15, b17 to b32, a3, a22, a4, a7, a12, a15, a19, a26, a27, a11, a13, a20 and a24 be respectively 2 with
When upper, the substituent group in bracket is same or different to each other.
7. heterocyclic compound according to claim 1, wherein the chemical formula 1 is selected from following compounds:
8. a kind of organic illuminating element, characterized by comprising: first electrode, second electrode and have it is described first electricity
1 layer or more of organic matter layer between pole and second electrode, 1 layer or more in the organic matter layer is comprising in claim 1 to 7
Described in any item heterocyclic compounds.
9. organic illuminating element according to claim 8, wherein the organic matter layer includes that hole injection layer or hole pass
Defeated layer,
The hole injection layer or hole transmission layer include the heterocyclic compound of the chemical formula 1.
10. organic illuminating element according to claim 8, wherein the organic matter layer includes electron transfer layer or electronics
Implanted layer,
The electron transfer layer or electron injecting layer include the heterocyclic compound of the chemical formula 1.
11. organic illuminating element according to claim 8, wherein the organic matter layer includes luminescent layer,
The luminescent layer includes the heterocyclic compound of the chemical formula 1.
12. organic illuminating element according to claim 11, wherein the luminescent layer also includes the change of following chemical formula 2
Close object:
Chemical formula 2
In the chemical formula 2,
R9 is hydrogen, deuterium, halogen group, itrile group, nitro, hydroxyl, aryloxy group, alkyl sulfenyl, artyl sulfo, alkyl sulfoxide base, virtue
It is base sulfoxide group, silicyl, boryl, substituted or unsubstituted alkyl, substituted or unsubstituted naphthenic base, substituted or unsubstituted
Alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted aryl alkyl, substituted or unsubstituted alkyl amine group, substitution or
Unsubstituted aralkyl amido, substituted or unsubstituted heteroaryl amido, substituted or unsubstituted arylamine group, substitution do not take
The aryl heteroaryl amido in generation, substituted or unsubstituted aryl phosphino- or substituted or unsubstituted heterocycle,
The integer that p is 0 to 6,
When p is 2 or more, the substituent group in bracket is same or different to each other,
L3 to L6 is same or different to each other, be each independently Direct Bonding, substituted or unsubstituted arlydene or substitution or
Unsubstituted heteroarylidene,
Ar2 to Ar5 is same or different to each other, and is each independently hydrogen, substituted or unsubstituted aryl or substituted or unsubstituted
Heteroaryl.
13. organic illuminating element according to claim 12, wherein the L3 to L6 is same or different to each other, respectively solely
On the spot for Direct Bonding or selected from following structures:
14. organic illuminating element according to claim 12, wherein the Ar2 to Ar5 is same or different to each other, respectively
It independently is hydrogen or selected from following structures:
15. organic illuminating element according to claim 11, wherein the luminescent layer also includes the change of following chemical formula 3
Close object:
Chemical formula 3
In the chemical formula 3,
R10 is hydrogen, deuterium, halogen group, itrile group, nitro, hydroxyl, aryloxy group, alkyl sulfenyl, artyl sulfo, alkyl sulfoxide base, virtue
It is base sulfoxide group, silicyl, boryl, substituted or unsubstituted alkyl, substituted or unsubstituted naphthenic base, substituted or unsubstituted
Alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted aryl alkyl, substituted or unsubstituted alkyl amine group, substitution or
Unsubstituted aralkyl amido, substituted or unsubstituted heteroaryl amido, substituted or unsubstituted arylamine group, substitution do not take
The aryl heteroaryl amido in generation, substituted or unsubstituted aryl phosphino- or substituted or unsubstituted heterocycle,
The integer that q is 0 to 7,
When q is 2 or more, the substituent group in bracket is same or different to each other,
L7 to L9 is same or different to each other, be each independently Direct Bonding, substituted or unsubstituted arlydene or substitution or
Unsubstituted heteroarylidene,
Ar6 to Ar8 is same or different to each other, and is each independently substituted or unsubstituted aryl or substituted or unsubstituted
Heteroaryl.
16. organic illuminating element according to claim 15, wherein the L7 to L9 is same or different to each other, respectively solely
On the spot for Direct Bonding or selected from following structures:
17. organic illuminating element according to claim 15, wherein the Ar6 to Ar8 is same or different to each other, respectively
Independently selected from following structures:
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| PCT/KR2017/007040 WO2018004319A2 (en) | 2016-07-01 | 2017-07-03 | Heterocyclic compound and organic light emitting element comprising same |
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| WO2006080638A1 (en) * | 2004-09-24 | 2006-08-03 | Lg Chem. Ltd. | New compound and organic light emitting device using the same (7) |
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| KR102332591B1 (en) * | 2014-06-09 | 2021-11-30 | 삼성디스플레이 주식회사 | Organic light-emitting devices |
| KR101757556B1 (en) * | 2014-11-27 | 2017-07-13 | 주식회사 엘지화학 | Multicyclic compound and organic electronic device using the same |
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| US20100025661A1 (en) * | 2004-07-02 | 2010-02-04 | Guofang Wang | Luminescent material and organic electroluminescent device using the same |
| KR20140045153A (en) * | 2012-10-08 | 2014-04-16 | 제일모직주식회사 | Compound for organic optoelectronic device, organic light emitting diode including the same and display including the organic light emitting diode |
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| WO2018004319A2 (en) | 2018-01-04 |
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| KR101939179B1 (en) | 2019-01-17 |
| WO2018004319A3 (en) | 2018-02-22 |
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