CN114605413A - Carboline derivative and application thereof - Google Patents
Carboline derivative and application thereof Download PDFInfo
- Publication number
- CN114605413A CN114605413A CN202210295186.2A CN202210295186A CN114605413A CN 114605413 A CN114605413 A CN 114605413A CN 202210295186 A CN202210295186 A CN 202210295186A CN 114605413 A CN114605413 A CN 114605413A
- Authority
- CN
- China
- Prior art keywords
- group
- unsubstituted
- substituted
- carbon atoms
- carboline derivative
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000463 material Substances 0.000 claims abstract description 47
- 239000010410 layer Substances 0.000 claims description 73
- 125000004432 carbon atom Chemical group C* 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 11
- 229910052805 deuterium Inorganic materials 0.000 claims description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 230000000903 blocking effect Effects 0.000 claims description 8
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- -1 phosphino group Chemical group 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 230000005525 hole transport Effects 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000012044 organic layer Substances 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 4
- 125000004437 phosphorous atom Chemical group 0.000 claims description 4
- 125000003367 polycyclic group Chemical group 0.000 claims description 4
- 238000006467 substitution reaction Methods 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 150000007942 carboxylates Chemical class 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 239000010452 phosphate Substances 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- MWPCBCGAQVXDCZ-UHFFFAOYSA-N 1-amino-1-nitramidoguanidine Chemical compound [N+](=O)([O-])NN(C(N)=N)N MWPCBCGAQVXDCZ-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000005104 aryl silyl group Chemical group 0.000 claims description 2
- 150000004832 aryl thioethers Chemical group 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 150000007857 hydrazones Chemical class 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- 125000004306 triazinyl group Chemical group 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 description 43
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000000524 functional group Chemical group 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 5
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 125000005605 benzo group Chemical group 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 4
- 239000002019 doping agent Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
- 238000007639 printing Methods 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 3
- 101100348848 Mus musculus Notch4 gene Proteins 0.000 description 3
- 101000767160 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) Intracellular protein transport protein USO1 Proteins 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- BKRRPNHAJPONSH-UHFFFAOYSA-N carbazole Chemical compound C1=CC=C2[C]3C=CC=CC3=NC2=C1 BKRRPNHAJPONSH-UHFFFAOYSA-N 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 101100446506 Mus musculus Fgf3 gene Proteins 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical compound C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 description 1
- HQDYNFWTFJFEPR-UHFFFAOYSA-N 1,2,3,3a-tetrahydropyrene Chemical compound C1=C2CCCC(C=C3)C2=C2C3=CC=CC2=C1 HQDYNFWTFJFEPR-UHFFFAOYSA-N 0.000 description 1
- ZFXBERJDEUDDMX-UHFFFAOYSA-N 1,2,3,5-tetrazine Chemical compound C1=NC=NN=N1 ZFXBERJDEUDDMX-UHFFFAOYSA-N 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical compound C1=NN=CN=N1 HTJMXYRLEDBSLT-UHFFFAOYSA-N 0.000 description 1
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- UDGKZGLPXCRRAM-UHFFFAOYSA-N 1,2,5-thiadiazole Chemical compound C=1C=NSN=1 UDGKZGLPXCRRAM-UHFFFAOYSA-N 0.000 description 1
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 1
- UUSUFQUCLACDTA-UHFFFAOYSA-N 1,2-dihydropyrene Chemical compound C1=CC=C2C=CC3=CCCC4=CC=C1C2=C43 UUSUFQUCLACDTA-UHFFFAOYSA-N 0.000 description 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
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- 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
- C07D471/12—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 three hetero rings
- C07D471/16—Peri-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/22—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 systems contains four or more hetero rings
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- C—CHEMISTRY; METALLURGY
- 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
- C07D491/22—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 four or more hetero rings
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- C07D495/22—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 four or more hetero rings
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Abstract
The invention relates to the technical field of organic electroluminescent materials, in particular to a carboline derivative and application thereof. The carboline derivative has a novel hollow seven-membered ring structure, has a bipolar property of conveying electrons and holes, and is suitable for being used as a material for an organic electroluminescent element; the material for organic electroluminescent elements containing the carboline derivative has the characteristics of low starting voltage, high luminous efficiency and high brightness. In addition, the carboline derivative of the invention has good thermal stability and film-forming property, and can prolong the service life when being applied to materials for organic electroluminescent elements, display devices and lighting devices, thereby reducing the power consumption and the manufacturing cost.
Description
Technical Field
The invention relates to the technical field of organic electroluminescent materials, in particular to a carboline derivative and application thereof.
Background
In recent years, organic electroluminescent display technologies have become mature, and some products have entered the market, but in the process of industrialization, many problems still need to be solved, especially, many problems still remain unsolved, such as carrier injection and transport performance, electroluminescent performance of materials, service life, color purity, matching between various materials and between various electrodes, and the like, of various organic materials used for manufacturing elements. Especially, the light emitting device has not yet achieved practical requirements in terms of luminous efficiency and lifetime, which greatly limits the development of OLED technology.
Organic electroluminescence is largely divided into fluorescence and phosphorescence, but according to the spin quantum statistical theory, the probability of singlet excitons and triplet excitons is 1:3, i.e., the theoretical limit of fluorescence from radiative transitions of singlet excitons is 25%, and the theoretical limit of fluorescence from radiative transitions of triplet excitons is 75%. It is urgent to use 75% of the energy of triplet excitons. Forrest et al in 1997 discovered that the phosphorescence electroluminescence phenomenon breaks through the limit of 25% quantum efficiency of organic electroluminescent materials, and arouses people's extensive attention to metal complex phosphorescence materials. Since then, much research has been conducted on phosphorescent materials.
The present invention has been made in view of the above circumstances.
Disclosure of Invention
In order to solve the above problems of the prior art, the present invention provides a carboline derivative and an application thereof, and the carboline derivative is used as a raw material of a material for an organic electroluminescent element, so that the material for the organic electroluminescent element and the organic electroluminescent element can be provided, wherein the starting voltage is reduced, the luminous efficiency is high, and the brightness is improved.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention provides a carboline derivative, the structure of which is shown as the formula (I):
wherein, W1、W2、W3、W4Each independently represents CR7Or N;
ring A and ring B are each independently selected from the group consisting of C5～C60Or a carbocyclic ring of C2～C60The heterocyclic ring of (4);
R1、R2、R3、R4、R7the same or different, each independently selected from the group consisting of: hydrogen, deuterium, fluorine, having C1～C40Straight chain alkyl of (2) having C1～C40Linear heteroalkyl group of (A) having C3～C40A branched or cyclic alkyl group having C3～C40A branched or cyclic heteroalkyl group of (A) having C2～C40Alkenyl or alkynyl group of (A), aralkyl group having 7 to 60 carbon atoms, aralkyl group having C1～C40Alkoxy group of (A), aryl group having 5 to 60 carbon atoms, aryloxy group having 5 to 60 carbon atoms, heteroaryl group having 2 to 60 carbon atoms, alkylsilyl group having 3 to 40 carbon atoms, arylsilyl group having 6 to 60 carbon atoms, amino group having 0 to 40 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, mercapto group, sulfonyl group, sulfinyl groupAny adjacent two or more adjacent substituent groups may be optionally joined or fused to form a mono-or polycyclic ring, with or without N, O, S, C or a P atom in the ring;
R5、R6selected from the group consisting of: aryl having 5 to 60 carbon atoms or heteroaryl having 2 to 60 carbon atoms, R5And R6May optionally be joined or fused to form a single or multiple rings, with or without N, O, S, C or a P atom in the ring;
l is selected from a single bond, an arylene group having 5 to 60 carbon atoms, a heteroarylene group having 2 to 60 carbon atoms, or a combination thereof;
n is an integer of 0 to 5;
R3、R4the same or different at each occurrence denotes mono-, poly-or no-substitution.
An aryl or aromatic group in the sense of the present invention contains 5 to 60 carbon atoms and a heteroaryl group in the sense of the present invention contains 2 to 60 carbon atoms and at least one heteroatom, with the proviso that the sum of carbon atoms and heteroatoms is at least 5; the heteroatom is preferably selected from N, O or S. Aryl or heteroaryl groups herein encompass monocyclic groups and polycyclic ring systems. Polycyclic rings can have two carbons that are two contiguous rings or two or more rings in common, referred to as "fused," where at least one of the rings is aromatic, e.g., the other rings can be cycloalkyls, cycloalkenyls, aryls, heterocyclics, and/or heteroaryls. In addition, multiple aryl or heteroaryl groups may also be linked by non-aromatic units such as C, N, O or S atoms, for example, as with systems in which two or more aryl groups are linked by, for example, a short alkyl group, such as fluorene, 9' -spirobifluorene, 9-diarylfluorene, triarylamine, diaryl ether, dibenzofuran, or dibenzothiophene, and the like.
The alkyl group used in the present invention means a monovalent functional group obtained by removing one hydrogen atom from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. As non-limiting examples thereof, there are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, hexyl and the like. Heteroalkyl means a hydrogen atom or-CH on an alkyl group2-substituted by at least one heteroatom selected from halogen, nitrile, N, O, S or silicon, as non-limiting examples difluoromethyl, trifluoromethyl, trifluoroethyl, pentafluoroethyl, nitrile, acetonitrile, methoxymethyl, methoxyethyl, trimethylsilyl, triisopropylsilyl and the like.
The alkenyl group used in the present invention means a monovalent functional group obtained by removing one hydrogen atom from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. As non-limiting examples thereof, there are vinyl, allyl, isopropenyl, 2-butenyl, and the like.
The alkynyl group used in the present invention means a monovalent functional group obtained by removing one hydrogen atom from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. As non-limiting examples thereof, there are ethynyl, 2-propynyl and the like.
In general, the cycloalkyl group, cycloalkenyl group according to the present invention means a monovalent functional group obtained by removing one hydrogen atom from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. As non-limiting examples thereof, there may be mentioned cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptyl, cycloheptenyl, and the like, wherein one or more-CH groups2The radicals may be replaced by the radicals mentioned above; furthermore, one or more hydrogen atoms may also be replaced by deuterium atoms, halogen atoms, or nitrile groups.
The heterocycloalkyl group used in the present invention refers to a monovalent functional group obtained by removing one hydrogen atom from a non-aromatic hydrocarbon having a nuclear number of 3 to 40. In this case, more than one carbon, preferably 1 to 3 carbons, in the ring is substituted with a heteroatom such as N, O or S. As non-limiting examples thereof, there are tetrahydrofuran, tetrahydrothiophene, morpholine, piperazine and the like.
The aryloxy group or heteroaryloxy group used in the present invention means a monovalent functional group represented by RO-, and R mentioned above is an aryl group having 6 to 60 carbon atoms or a heteroaryl group having 5 to 60 carbon atoms. As non-limiting examples of such aryloxy or heteroaryloxy groups, there may be mentioned phenoxy, naphthoxy, biphenyloxy, 2-pyridyloxy, 3-pyridyloxy, 4-pyridyloxy and the like.
Aryl or heteroaryl according to the invention, in particular refers to groups derived from: benzene, naphthalene, anthracene, benzanthracene, phenanthrene, pyrene,
Perylene, fluoranthene, tetracene, pentacene, benzopyrene, biphenyl, terphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis-or trans-indenofluorene, cis-or trans-indenocarbazole, cis-or trans-indolocarbazole, triindene, isotridendene, spirotriindene, spiroisotridendene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene, pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo [5,6 ] indole, perylene, anthracene, phenanthrene, perylene]Quinoline, benzo [6,7 ]]Quinoline, benzo [7,8 ]]Quinoline, phenothiazine, phenoxazine, pyrazole, indazole, imidazole, benzimidazole, naphthoimidazole, phenanthroimidazole, pyridoimidazole, pyrazinoimidazole, quinoxaloimidazole, oxazole, benzoxazole, naphthooxazole, anthraoxazole, phenanthroixazole, isoxazole, 1, 2-thiazole, 1, 3-thiazole, benzothiazole, pyridazine, hexaazatriphenylene, benzopyridazine, pyrimidine, benzopyrimidine, quinoxaline, 1, 5-diaza-thracene, 2, 7-diaza, 2, 3-diaza-pyrene, 1, 6-diaza-pyrene, 1, 8-diaza-pyrene, 4,5,9, 10-tetraazaperylene, pyrazine, phenazine, phenoxazine, phenothiazine, fluorescent red ring, naphthyridine, azacarbazole, benzocarbazine, carboline, phenanthroline, 1,2, 3-triazole, 1,2, 4-triazole, benzotriazole, 1,2, 3-oxadiazole, 1,2, 4-oxadiazole, 1,2, 5-oxadiazole, 1,3, 4-oxadiazole, 1,2, 3-thiadiazole, 1,2, 4-thiadiazole, 1,2, 5-thiadiazole, 1,3, 4-thiadiazole, 1,3, 5-triazine, 1,2, 4-triazine, 1,2, 3-triazine, tetrazole, 1,2,4, 5-tetrazine, 1,2,3, 4-tetrazine, 1,2,3, 5-tetrazine, purine, pteridine, indolizine, and benzothiadiazole, or a group derived from a combination of these systems.
As used herein, "a combination thereof" or "group" means that one or more members of the applicable list are combined to form a known or chemically stable arrangement that one of ordinary skill in the art can envision from the applicable list. For example, alkyl and deuterium can be combined to form a partially or fully deuterated alkyl; halogen and alkyl groups may be combined to form haloalkyl substituents, such as trifluoromethyl and the like; and halogen, alkyl, and aryl groups may be combined to form haloaralkyl groups.
Preferably, the carboline derivative is selected from one or more of formula (I) -1 to formula (I) -22:
wherein R is1、R2、R3、R4、W1、W2、W3、W4Have the same meaning as previously defined; each G is independently selected from O, S or NAr1；
Ar1Selected from the group consisting of: an aryl group having 5 to 60 carbon atoms or a heteroaryl group having 2 to 60 carbon atoms.
Preferably, the heteroaryl group is selected from the group consisting of the following groups II-1 to II-17:
wherein,
Z1、Z2each independently selected from the group consisting of hydrogen, deuterium, halogen, hydroxy, nitrile, nitro, amino, amidino, hydrazine, hydrazone, carboxy or carboxylate thereof, sulfonic acid or carboxylate thereofSulfonate, phosphate or phosphate thereof, C1～C60Alkyl radical, C2～C60Alkenyl radical, C2～C60Alkynyl, C1～C60Alkoxy radical, C3～C60Cycloalkyl radical, C3～C60Cycloalkenyl, substituted or unsubstituted C6～C60Aryl, substituted or unsubstituted C6～C60Aryloxy, substituted or unsubstituted C6～C60An arylthioether group, or a substituted or unsubstituted C2～C60Heterocyclic aryl groups;
x1 represents an integer of 1 to 4; x2 represents an integer of 1 to 3; x3 represents 1 or 2; x4 represents an integer of 1 to 6; x5 represents an integer of 1 to 5;
T1represents O, S, CR 'R "or NAr';
r 'and R' are each independently selected from hydrogen, deuterium, C1～C60Alkyl of (C)1～C60With heteroalkyl, substituted or unsubstituted C6～C60Aryl, substituted or unsubstituted C6～C60Arylamino, or substituted or unsubstituted C2～C60Heterocyclic aryl, R 'and R' may optionally be joined or fused to form one or more additional substituted or unsubstituted rings, with or without one or more heteroatoms N, P, B, O or S in the ring so formed; preferably, R', R "are methyl, phenyl or fluorenyl;
ar' is selected from C1～C60Alkyl of (C)1～C60Heteroalkyl of (a), C3～C60Cycloalkyl, substituted or unsubstituted C6～C60Aryl, substituted or unsubstituted C6-C60Condensed ring aryl, substituted or unsubstituted C6～C60Arylamino, or substituted or unsubstituted C2～C60Heterocyclic aryl groups; preferably, Ar' is methyl, ethyl, phenyl, biphenyl or naphthyl;
Preferably, R is1、R2、R3、R4、R7Each independently selected from hydrogen, deuterium, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms.
Further, said R1、R2、R3、R4、R7At least one of which is selected from hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, and substituted or unsubstituted triazinyl.
Preferably, the carboline derivative is selected from one or more of the following structures represented by D01 to D252:
wherein, T2-is selected from-O-, -S-, or one of the following structures:
and represents a bond.
The invention also provides application of the carboline derivative in an organic electroluminescent element.
Preferably, the carboline derivative is used as a light-emitting layer material, a hole transport layer material, a hole blocking layer material or a capping layer material in an organic electroluminescent element.
The present invention also provides an organic electroluminescent element comprising: the organic light-emitting diode comprises a first electrode, a second electrode, a capping layer and at least one organic layer positioned between the first electrode and the second electrode, wherein at least one of the organic layer or the capping layer comprises the carboline derivative.
The organic electroluminescent element includes a cathode, an anode, and at least one light-emitting layer. In addition to these layers, it may also comprise further layers, for example in each case one or more hole-injecting layers, hole-transporting layers, hole-blocking layers, electron-transporting layers, electron-injecting layers, exciton-blocking layers, electron-blocking layers and/or charge-generating layers. An intermediate layer having, for example, exciton blocking function can likewise be introduced between the two light-emitting layers. However, it should be noted that each of these layers need not be present. The organic electroluminescent device described herein may include one light emitting layer, or it may include a plurality of light emitting layers. That is, a plurality of light-emitting compounds capable of emitting light are used in the light-emitting layer. Particularly preferred are systems with three light-emitting layers, wherein the three layers can exhibit blue, green and red light emission. If more than one light-emitting layer is present, at least one of these layers comprises the carboline derivative of the invention according to the invention.
In the other layers of the organic electroluminescent element according to the invention, in particular in the light-emitting layer, the electron-transporting layer and in the hole-blocking layer and the thin-film encapsulation layer, all materials can be used in the manner conventionally used according to the prior art. The person skilled in the art will thus be able to use all materials known for organic electroluminescent elements in combination with the light-emitting layer according to the invention without inventive effort.
Preference is furthermore given to organic electroluminescent elements in which one or more layers are applied by means of a sublimation process in which the temperature in a vacuum sublimation apparatus is below 10-5Pa, preferably less than 10-6Pa is applied by vapor deposition. However, the initial pressure may also be even lower, e.g. below 10-7Pa。
Preference is likewise given to organic electroluminescent elements in which one or more layers are applied by means of an organic vapor deposition method or by means of carrier gas sublimation, where 10-5The material is applied under a pressure between Pa and 1 Pa. A particular example of this method is the organic vapour jet printing method, in which the material is applied directly through a nozzle and is therefore structured.
Preference is furthermore given to organic electroluminescent elements in which one or more layers are produced from solution, for example by spin coating, or by means of any desired printing method, for example screen printing, flexographic printing, offset printing, photoinitiated thermal imaging, thermal transfer, ink-jet printing or nozzle printing. Soluble compounds, for example, are obtained by appropriate substitution of a compound of formula (I). These methods are also particularly suitable for oligomers, dendrimers and polymers. Furthermore, hybrid methods are possible, in which, for example, one or more layers are applied from solution and one or more further layers are applied by vapor deposition.
Further, the organic layer may further include one or more selected from an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, a hole transport layer, a hole injection layer, a light emitting layer, and a light refraction layer.
The organic electroluminescent element of the present invention may be either a top emission light element or a bottom emission light element. The structure and the production method of the organic electroluminescent element of the present invention are not limited. The organic electroluminescent element prepared by the compound can reduce the starting voltage and improve the luminous efficiency and brightness.
The invention also provides a display device comprising the organic electroluminescent element.
The invention also provides a lighting device comprising the organic electroluminescent element.
The material for organic electroluminescent elements of the present invention contains the carboline derivative of the present invention. The material for an organic electroluminescent element may be formed using the compound of the present invention alone, or may contain other compounds.
The carboline derivative of the present invention contained in the material for an organic electroluminescent element of the present invention can be used as a host material. In this case, the material for an organic electroluminescent element of the present invention may contain another compound as a dopant.
The material for an organic electroluminescent element of the present invention can also be used as a material for a hole transport layer, an enhancement layer, a light-emitting layer, an electron transport layer, a charge generation layer, an electron blocking layer, an encapsulation layer, or a photorefractive layer.
Compared with the prior art, the invention has the beneficial effects that:
the carboline derivative has a novel structure of internal seven-membered ring carboline, has a bipolar property of transporting electrons and holes, and is suitable for being used as a material for an organic electroluminescent element; the material for organic electroluminescent elements containing the carboline derivative has the characteristics of low starting voltage, high luminous efficiency and high brightness. In addition, the carboline derivative of the invention has good thermal stability and film-forming property, and can prolong the service life when being applied to materials for organic electroluminescent elements, display devices and lighting devices, thereby reducing the power consumption and the manufacturing cost.
Drawings
FIG. 1 is a schematic view of an organic light emitting device 100 according to the present invention;
in fig. 1, 101 denotes a substrate, 102 denotes an anode, 103 denotes a hole injection layer, 104 denotes a hole transport layer, 105 denotes an electron blocking layer, 106 denotes a light emitting layer, 107 denotes a hole blocking layer, 108 denotes an electron transport layer, 109 denotes an electron injection layer, 110 denotes a cathode, and 111 denotes a capping layer (CPL).
FIG. 2 is a schematic view of an inverted organic light emitting device 200 according to the present invention;
in fig. 2, 201 denotes a substrate, 202 denotes a cathode, 203 denotes a light-emitting layer, 204 denotes a hole-transporting layer, and 205 denotes an anode.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the technical solutions of the present invention will be described in detail below. It is to be understood that the described embodiments are merely exemplary of the invention, and not restrictive of the full scope of the invention. All other embodiments, which can be derived by a person skilled in the art from the examples given herein without any inventive step, are within the scope of the present invention.
The following examples illustrate the performance of OLED materials and devices as follows:
OLED element performance detection conditions:
luminance and chromaticity coordinates: testing with a photosresearch PR-715 spectrum scanner;
current density and lighting voltage: testing using a digital source table Keithley 2420;
power efficiency: tested using NEWPORT 1931-C;
and (3) testing the service life: an LTS-1004AC life test apparatus was used.
Example 1
The preparation method of the intermediate A1 comprises the following steps:
the first step is as follows: preparation of Compound Int-1
Dissolving 55.0mmol of tryptamine and 55.0mmol of raw material aldehyde in 250mL of dichloromethane, dropwise adding 55.0mmol of trifluoroacetic acid, stirring for reacting for 12 hours, pouring the reaction solution into 250mL of 5% sodium hydroxide ice water solution, extracting with dichloromethane, collecting an organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain a compound Int-1, namely a white solid, wherein the yield is as follows: 90 percent.
The second step: preparation of Compound Int-2
Dissolving 20.0mmol of intermediate Int-1 in 200mL of xylene, adding 60.0mmol of manganese dioxide, heating to reflux and stirring for reaction for 8 hours, adding 40.0mmol of manganese dioxide, heating to reflux and stirring for reaction for 8 hours, cooling to room temperature, filtering, washing a filter cake with tetrahydrofuran, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain a compound Int-2, namely a white solid, wherein the yield is as follows: 86 percent.
The third step: preparation of Compound A1
Under the protection of nitrogen, 20.0mmol of intermediateInt-2 was dissolved in 100mL of xylene, and 30.0mmol of cesium carbonate and 0.2mmol of Pd were added2(dba)3And 0.4mmol of XPhos, heating to 120 ℃, stirring for reaction for 12 hours, cooling to room temperature, adding 50mL of water, extracting with ethyl acetate, collecting an organic phase, drying, filtering, concentrating the filtrate under reduced pressure to dryness, and separating and purifying by using a silica gel column to obtain a compound A1, a white solid, a yield: 66%, HRMS: m/z 353.0853[ M + H]+，1HNMR(δ、CDCl3)：9.24～9.22(1H,d)；8.86～8.82(1H,m)；8.57～8.48(3H,m)；8.29～8.27(2H,m)；8.15～8.08(3H,m)；7.97～7.95(1H,d)；7.45～7.34(2H,m)。
Example 2
A method for preparing compound D01, comprising the steps of:
the first step is as follows: preparation of Compound Int-3
20.0mmol of A1, 24.0mmol of pinacol diboron, 30.0mmol of anhydrous potassium acetate and 0.2mmol of PdCl2(dppf) is dissolved in 50mL of DMF, the mixture is heated to 100 ℃ under the protection of nitrogen, stirred and reacted for 12 hours, the mixture is cooled to room temperature, 200mL of water is added for dilution, the mixture is extracted by ethyl acetate, an organic phase is collected, dried and filtered, filtrate is concentrated under reduced pressure to be dry, and the mixture is separated and purified by a silica gel column to obtain a compound Int-3, a white solid and yield: 85 percent.
The second step is that: preparation of Compound D01
Under the protection of nitrogen, 12.0mmol of intermediate Int-3, 10.0mmol of 9- (3-bromophenyl) carbazole, 40.0mmol of anhydrous sodium carbonate and 0.1mmol of Pd (PPh)3)4Mixing, adding 50mL of toluene, 30mL of ethanol and 25mL of water, heating to reflux, stirring, reacting for 10 hr, cooling to room temperature, diluting with 50mL of water, extracting with ethyl acetate, and vacuum concentrating the organic phaseConcentration to dryness and separation and purification by silica gel column gave compound D01 in yield: 87%, HRMS: m/z 560.2136[ M + H ]]+，1HNMR(δ、CDCl3)：9.24(1H,s)；8.77(1H,s)；8.57～8.48(3H,m)；8.43～8.41(1H,d)；8.35(1H,s)；8.27～8.25(1H,d)；8.19～8.10(5H,m)；7.62～7.59(1H,m)；7.45～7.26(10H,m)；7.06(1H,s)。
Referring to the synthetic methods similar to those of the above examples 1 and 2, the compounds shown in the following table 1 were prepared;
TABLE 1
Wherein T in reactant 12O, S or NPh; t in reactant 22Is O, S, C (CH)3)2Or NPh.
Example 3
Preparation of compound D39:
10.0mmol of Compound D37 was dissolved in 150mL of dry THF, 12.0mmol of iodine and 60.0mmol of propylene oxide were added, the mixture was reacted at room temperature under stirring with an ultraviolet lamp (254nm) for 2 days, 50mL of a saturated aqueous solution of sodium thiosulfate was added, the mixture was filtered, the filter cake was washed with water and ethyl acetate, and the solid was isolated and purified by a silica gel column to give Compound D39, T2O, white solid, yield: 76%, MS (MALDI-TOF): m/z 624.2084[ M + H ]]+；1HNMR(δ、CDCl3)：9.21～9.19(1H,d)；8.84～8.78(3H,m)；8.53～8.47(4H,m)；8.32～8.18(4H,m)；8.12～8.09(2H,m)；8.01～7.94(2H,m)；7.53～7.45(2H,m)；7.39～7.26(7H,m)。
Preparation of Compound D40, T according to a similar Synthesis procedure as described in example 3 above2O, white solid, yield: 80%, MS (MALDI-TOF): m/z 624.2084[ M + H ]]+；1HNMR(δ、CDCl3)：9.23(1H,s)；8.97(1H,s)；8.83(1H,s)；8.77～8.71(2H,m)；8.62～8.51(4H,m)；8.37～8.35(1H,d)；8.27～8.21(2H,m)；8.04～7.96(3H,m)；7.87～7.83(1H,m)；7.62～7.56(2H,m)；7.42～7.26(7H,m)。
Example 4
Preparation of compound D229:
16.5mmol of Compound A1 were dissolved in 80mL of dry toluene, and 15.0mmol of benzofuran [2,3-a ] were added under nitrogen protection]Carbazole or benzo [4,5 ]]Thiophene [2,3-a ]]Azolocarbazide or 11-substituted-11, 12-indolino [2,3-a]Carbazole and 22.5mmol sodium tert-butoxide, and then 0.1mmol Pd2(dba)3CHCl3And 0.02mL of 10% toluene solution of phosphorus tri-tert-butyl, heating to 100 ℃, stirring for reaction for 15 hours, cooling to room temperature, adding 50mL of water for dilution, extracting with dichloromethane, collecting the organic phase, drying, filtering, concentrating the filtrate under reduced pressure, drying, and using silica gelSeparating and purifying the column to obtain a compound D229;
T2o, yellow solid, yield: 86%, MS (MALDI-TOF): m/z 574.1933[ M + H ]]+；1HNMR(δ、CDCl3)：9.24(1H,s)；8.98(1H,s)；8.89(1H,s)；8.74～8.69(2H,m)；8.48～8.40(3H,m)；8.27～8.24(2H,m)；8.15～8.03(4H,m)；7.84～7.81(2H,m)；7.64～7.59(1H,m)；7.49～7.29(6H,m)。
T2S, yellow solid, yield: 85%, MS (MALDI-TOF): m/z 590.1695[ M + H ]]+；1HNMR(δ、CDCl3)：9.24(1H,s)；8.87～8.85(2H,m)；8.74～8.72(1H,m)；8.61～8.54(4H,m)；8.31～8.27(2H,m)；8.15～8.02(6H,m)；7.62～7.58(1H,m)；7.46～7.25(6H,m)。
T2NPh, yellow solid, yield: 74%, MS (MALDI-TOF): m/z 649.2402[ M + H ]]+；1HNMR(δ、CDCl3)：9.25(1H,s)；8.98(1H,s)；8.93～8.91(1H,d)；8.75～8.72(2H,m)；8.48～8.42(4H,m)；8.29～8.27(1H,d)；8.15～8.02(5H,m)；7.78～7.73(2H,m)；7.56～7.48(4H,m)；7.45～7.28(7H,m)。
Referring to a similar synthetic procedure to example 4 above, the compounds shown in table 2 below were prepared:
TABLE 2
Wherein T in reactant 12O, S or NPh; t in reactant 22Is O, S, C (CH)3)2Or NPh.
Preparation of organic electroluminescent element (shown in FIGS. 1 and 2)
Comparative example 1
A mixture of the following compounds a1 and a2, in which the mass ratio of a1 to a2 was 11:9, was used as a green-light-emitting host material, compound B as a green-light-emitting dopant material, compound C as a hole-injecting material, compound D as a hole-transporting material, compound E as a red-light-emitting material, compound F as a red-light-emitting dopant material, compound G as an electron-transporting dopant material, and LiQ as an electron-transporting host material.
The compound
An organic electroluminescent element was prepared as a green light by sequentially depositing an ITO glass layer on the surface of the ITO glass layer by an EL deposition apparatus manufactured by DOV.
The compound
An organic electroluminescent element was prepared as a red light by depositing an EL evaporator manufactured by DOV on ITO glass in this order.
Test example 1
By replacing the compounds A1 and A2 in comparative example 1 with any one or more of the compounds D01 to D223 of the present invention, a green organic electroluminescent element was prepared in the same manner as in comparative example 1,
the element structure is as follows:
the results of measuring the properties of the obtained green organic electroluminescent element are shown in Table 3, in which the driving voltage (V), the current efficiency (LE), and the full width at half maximum (FWHM) were measured in the elementHas a current density of 10mA/cm2The conditions were obtained and the voltage, LE, FWHM and LT 90% were normalized to the data compared to the comparative element.
TABLE 3 Green light element data
As is clear from Table 3, the replacement of Compound A2 in comparative example 1 with the Compound of the present invention as the host material has the advantages of low driving voltage, high current efficiency, etc., and the initial current density at the element is 50mA/cm2In the case of (2), the LT 90% lifetime of the element is even increased by several times.
The compounds of the present invention are distinguished from a2 in that a2 as an n-type host has a triazine-linked triphenylene structure, is sterically bulky, and is not favorable for close packing with a1 as a p-type host. The carboline ring has stronger plane conjugation capability and small steric hindrance, is uniformly mixed with a material steamed with A1 to form a film, and is more beneficial to the formation of excitons, so that the carboline ring is more excellent in film formation and charge transmission compared with the material A1+ A2, the charge transmission in the element is more balanced, and the element performance and the service life are improved.
The properties of only some of the compounds D01-D223 are listed in Table 3, and the properties of other compounds are substantially identical to the structures of the compounds listed in the Table, and are not listed any more due to space limitation.
Test example 2
A red light element was produced according to the method of comparative example 1, wherein the compound E in comparative example 1 was replaced with any one or more of the compounds D224 to D252 of the present invention, an organic electroluminescent element was produced,
the element structure is as follows:
the results of measuring the properties of the obtained element are shown in Table 4, in which the driving voltage (V), the current efficiency (LE), and the full width at half maximum (FWHM) were set to be 10mA/cm in current density of the element2The conditions were obtained and the voltage, LE, FWHM and LT 90% were normalized to the data compared to the comparative element.
TABLE 4 Red light element data
As can be seen from the element data in table 4, the carboline derivative of the present invention has a significantly reduced driving voltage and improved luminous efficiency compared to comparative example 1. The initial current density of the element is 50mA/cm2Under the conditions of (1), element LT 90%The lifetime has significant advantages.
In Table 4, only some of the compounds in D224-D252 are listed, and the properties of other compounds are substantially identical to the structures of the compounds listed in the table, and are not listed any more due to space limitation.
Although the invention has been described in detail hereinabove with respect to a general description and specific embodiments thereof, it will be apparent to those skilled in the art that modifications or improvements may be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.
Claims (10)
1. A carboline derivative is characterized in that the structure of the carboline derivative is shown as the formula (I):
wherein, W1、W2、W3、W4Each independently represents CR7Or N;
ring A and ring B are each independently selected from the group consisting of C5～C60Or a carbocyclic ring of C2～C60The heterocyclic ring of (1);
R1、R2、R3、R4、R7the same or different, each independently selected from the group consisting of: hydrogen, deuterium, fluorine, having C1～C40Straight chain alkyl of (2) having C1～C40Linear heteroalkyl group of (A) having C3～C40A branched or cyclic alkyl group having C3～C40A branched or cyclic heteroalkyl group of (2), having C2～C40Alkenyl or alkynyl group of (A), aralkyl group having 7 to 60 carbon atoms, aralkyl group having C1～C40Alkoxy group of (A), aryl group having 5 to 60 carbon atoms, aryloxy group having 5 to 60 carbon atoms, heteroaryl group having 2 to 60 carbon atoms, alkylsilyl group having 3 to 40 carbon atomsA group, an arylsilyl group having 6 to 60 carbon atoms, an amino group having 0 to 40 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a mercapto group, a sulfonyl group, a sulfinyl group, a phosphino group, a phosphinyloxy group, or a group represented by formula (II), any adjacent two or more adjacent substituent groups may be optionally joined or fused to form a monocyclic or polycyclic ring, with or without N, O, S, C or P atoms in the ring;
R5、R6selected from the group consisting of: aryl having 5 to 60 carbon atoms or heteroaryl having 2 to 60 carbon atoms, R5And R6May optionally be joined or fused to form a single or multiple rings, with or without N, O, S, C or a P atom in the ring;
l is selected from a single bond, an arylene group having 5 to 60 carbon atoms, a heteroarylene group having 2 to 60 carbon atoms, or a combination thereof;
n is an integer of 0 to 5;
R3、R4the same or different at each occurrence denotes mono-, poly-or no-substitution.
2. The carboline derivative of claim 1, wherein the carboline derivative is selected from one or more of formula (I) -1 to formula (I) -22:
wherein R is1、R2、R3、R4、W1、W2、W3、W4Has the same meaning as defined in claim 1; each G is independently selected from O, S or NAr1；
Ar1Selected from the group consisting of: an aryl group having 5 to 60 carbon atoms or a heteroaryl group having 2 to 60 carbon atoms.
3. The carboline derivative of claim 1 or 2, wherein the heteroaryl group is selected from the group consisting of groups represented by II-1 to II-17:
wherein,
Z1、Z2each independently selected from the group consisting of hydrogen, deuterium, halogen, hydroxy, nitrile, nitro, amino, amidino, hydrazine, hydrazone, carboxy or carboxylate thereof, sulfonic or sulfonate thereof, phosphoric or phosphate thereof, C1～C60Alkyl radical, C2～C60Alkenyl radical, C2～C60Alkynyl, C1～C60Alkoxy radical, C3～C60Cycloalkyl radical, C3～C60Cycloalkenyl radical, substituted or unsubstituted C6～C60Aryl, substituted or unsubstituted C6～C60Aryloxy, substituted or unsubstituted C6～C60An arylthioether group, or a substituted or unsubstituted C2～C60Heterocyclic aryl groups;
x1 represents an integer of 1 to 4; x2 represents an integer of 1 to 3; x3 represents 1 or 2; x4 represents an integer of 1 to 6; x5 represents an integer of 1 to 5;
T1represents O, S, CR 'R "or NAr';
r 'and R' are each independently selected from hydrogen, deuterium, C1～C60Alkyl of (C)1～C60With heteroalkyl, substituted or unsubstituted C6～C60Aryl, substituted or unsubstituted C6～C60Arylamino radicals, or radicals derived fromSubstituted or unsubstituted C2～C60Heterocyclic aryl, R 'and R' may optionally be joined or fused to form one or more additional substituted or unsubstituted rings, with or without one or more heteroatoms N, P, B, O or S in the ring so formed; preferably, R', R "are methyl, phenyl or fluorenyl;
ar' is selected from C1～C60Alkyl of (C)1～C60Heteroalkyl of (a), C3～C60Cycloalkyl, substituted or unsubstituted C6～C60Aryl, substituted or unsubstituted C6-C60Condensed ring aryl, substituted or unsubstituted C6～C60Arylamino, or substituted or unsubstituted C2～C60Heterocyclic aryl groups; preferably, Ar' is methyl, ethyl, phenyl, biphenyl or naphthyl;
4. The carboline derivative according to any one of claims 1 to 3, wherein R is1、R2、R3、R4、R7Each independently selected from hydrogen, deuterium, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 3 to 30 carbon atoms;
preferably, R1、R2、R3、R4、R7At least one of which is selected from hydrogen, deuterium, substituted or unsubstituted phenyl, substituted or unsubstituted biphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrimidyl, and substituted or unsubstituted triazinyl.
5. The carboline derivative of any one of claims 1-4, wherein the carboline derivative is selected from one or more of the structures represented by D01-D252:
wherein, T2-is selected from-O-, -S-, or one of the following structures:
and represents a bond.
6. Use of the carboline derivative according to any one of claims 1 to 5 in an organic electroluminescent device.
7. Use according to claim 6, characterized in that the carboline derivative is used as a light-emitting layer material, a hole transport layer material, a hole blocking layer material, an electron transport layer material or a capping layer material in an organic electroluminescent element.
8. An organic electroluminescent element, comprising: a first electrode, a second electrode, a capping layer, and at least one organic layer between the first electrode and the second electrode, at least one of the organic layer or capping layer comprising the carboline derivative of any one of claims 1-5.
9. A display device comprising the organic electroluminescent element according to claim 8.
10. A lighting device comprising the organic electroluminescent element according to claim 8.
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| CN108864108A (en) * | 2018-06-28 | 2018-11-23 | 宁波卢米蓝新材料有限公司 | A kind of fused ring compound and its preparation method and application |
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