CN113234010A - Compound, electron transport material, organic electroluminescent device and display device - Google Patents
Compound, electron transport material, organic electroluminescent device and display device Download PDFInfo
- Publication number
- CN113234010A CN113234010A CN202110496937.2A CN202110496937A CN113234010A CN 113234010 A CN113234010 A CN 113234010A CN 202110496937 A CN202110496937 A CN 202110496937A CN 113234010 A CN113234010 A CN 113234010A
- Authority
- CN
- China
- Prior art keywords
- substituted
- unsubstituted
- reaction
- compound
- organic electroluminescent
- 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.)
- Pending
Links
- 239000000463 material Substances 0.000 title claims abstract description 93
- 150000001875 compounds Chemical class 0.000 title claims abstract description 54
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 27
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 22
- -1 pyridopyrazinyl Chemical group 0.000 claims description 20
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 17
- 229910052805 deuterium Inorganic materials 0.000 claims description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 11
- 239000004305 biphenyl Substances 0.000 claims description 11
- 235000010290 biphenyl Nutrition 0.000 claims description 11
- 125000001624 naphthyl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000005549 heteroarylene group Chemical group 0.000 claims description 8
- 125000005580 triphenylene group Chemical group 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000001769 aryl amino group Chemical group 0.000 claims description 6
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 6
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 6
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 6
- 125000005561 phenanthryl group Chemical group 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000005493 quinolyl group Chemical group 0.000 claims description 6
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000004306 triazinyl group Chemical group 0.000 claims description 6
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000004982 aromatic amines Chemical class 0.000 claims description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 2
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical compound N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 claims description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 2
- 125000005556 thienylene group Chemical group 0.000 claims description 2
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 239000007787 solid Substances 0.000 abstract description 69
- 230000002035 prolonged effect Effects 0.000 abstract description 4
- 238000009825 accumulation Methods 0.000 abstract description 3
- 230000009286 beneficial effect Effects 0.000 abstract description 3
- 230000007704 transition Effects 0.000 abstract description 3
- 150000003918 triazines Chemical class 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 151
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 96
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 93
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 64
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 46
- 239000000843 powder Substances 0.000 description 33
- 238000002347 injection Methods 0.000 description 32
- 239000007924 injection Substances 0.000 description 32
- 239000012074 organic phase Substances 0.000 description 31
- 229910000027 potassium carbonate Inorganic materials 0.000 description 23
- 238000001704 evaporation Methods 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 20
- 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 19
- 230000005525 hole transport Effects 0.000 description 19
- 238000000034 method Methods 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 18
- 230000008020 evaporation Effects 0.000 description 14
- IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 239000002019 doping agent Substances 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 229910052763 palladium Inorganic materials 0.000 description 9
- 235000011056 potassium acetate Nutrition 0.000 description 9
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- GMGWXLPFRHYWAS-UHFFFAOYSA-N 3-bromo-5-chlorophenol Chemical compound OC1=CC(Cl)=CC(Br)=C1 GMGWXLPFRHYWAS-UHFFFAOYSA-N 0.000 description 8
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000010408 film Substances 0.000 description 6
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 101000766357 Ruditapes philippinarum Big defensin Proteins 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 4
- WCTHBMRGQJZEBQ-UHFFFAOYSA-N ClN(NC(C1=CC(C=CC=C2)=C2C2=CC=CC=C12)=C1)N=C1C1=CC=CC=C1 Chemical compound ClN(NC(C1=CC(C=CC=C2)=C2C2=CC=CC=C12)=C1)N=C1C1=CC=CC=C1 WCTHBMRGQJZEBQ-UHFFFAOYSA-N 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- RSGRRCWDCXLEHS-UHFFFAOYSA-N 1-bromo-3-chloro-5-iodobenzene Chemical compound ClC1=CC(Br)=CC(I)=C1 RSGRRCWDCXLEHS-UHFFFAOYSA-N 0.000 description 2
- ZDPXTYKMHYSMQW-UHFFFAOYSA-N 2,6-dibromo-4-chloropyridine Chemical compound ClC1=CC(Br)=NC(Br)=C1 ZDPXTYKMHYSMQW-UHFFFAOYSA-N 0.000 description 2
- ZIYRDJLAJYTELF-UHFFFAOYSA-N 2-bromo-4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1Br ZIYRDJLAJYTELF-UHFFFAOYSA-N 0.000 description 2
- JZAFCDUOMYNXTO-UHFFFAOYSA-N 9-(4-bromophenyl)phenanthrene Chemical compound C1=CC(Br)=CC=C1C1=CC2=CC=CC=C2C2=CC=CC=C12 JZAFCDUOMYNXTO-UHFFFAOYSA-N 0.000 description 2
- RSQXKVWKJVUZDG-UHFFFAOYSA-N 9-bromophenanthrene Chemical compound C1=CC=C2C(Br)=CC3=CC=CC=C3C2=C1 RSQXKVWKJVUZDG-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- UNXISIRQWPTTSN-UHFFFAOYSA-N boron;2,3-dimethylbutane-2,3-diol Chemical compound [B].[B].CC(C)(O)C(C)(C)O UNXISIRQWPTTSN-UHFFFAOYSA-N 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- QCSLIRFWJPOENV-UHFFFAOYSA-N (2-fluorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1F QCSLIRFWJPOENV-UHFFFAOYSA-N 0.000 description 1
- XDBHWPLGGBLUHH-UHFFFAOYSA-N (3-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(C#N)=C1 XDBHWPLGGBLUHH-UHFFFAOYSA-N 0.000 description 1
- QBLFZIBJXUQVRF-UHFFFAOYSA-N (4-bromophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Br)C=C1 QBLFZIBJXUQVRF-UHFFFAOYSA-N 0.000 description 1
- HYZNIURBDZXTGX-UHFFFAOYSA-N (4-pyridin-3-ylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CN=C1 HYZNIURBDZXTGX-UHFFFAOYSA-N 0.000 description 1
- SFKMVPQJJGJCMI-UHFFFAOYSA-N 2-chloro-4-phenylquinazoline Chemical compound C=12C=CC=CC2=NC(Cl)=NC=1C1=CC=CC=C1 SFKMVPQJJGJCMI-UHFFFAOYSA-N 0.000 description 1
- UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- BQHRJUASXACWDG-UHFFFAOYSA-N ClN1NC(=CC(=N1)Cl)C1=CC=CC=C1 Chemical compound ClN1NC(=CC(=N1)Cl)C1=CC=CC=C1 BQHRJUASXACWDG-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L Cs2CO3 Substances [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000010295 mobile communication Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- JLKDVMWYMMLWTI-UHFFFAOYSA-M potassium iodate Chemical compound [K+].[O-]I(=O)=O JLKDVMWYMMLWTI-UHFFFAOYSA-M 0.000 description 1
- 239000001230 potassium iodate Substances 0.000 description 1
- 235000006666 potassium iodate Nutrition 0.000 description 1
- 229940093930 potassium iodate Drugs 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
Abstract
The application provides a compound of general formula (I) which can be used in an electron transport material. The compound has the parent structure of s-triphenylphenanthrene substituted triazine, has high bond energy among atoms, has good thermal stability and is beneficial toThe solid state accumulation between molecules has strong transition capability of electrons. When the organic electroluminescent material is used as an electron transport material, the driving voltage of the organic electroluminescent device is effectively reduced, the current efficiency of the organic electroluminescent device is improved, and the service life of the organic electroluminescent device is prolonged. The present application also provides an organic electroluminescent device and a display device comprising the compound of formula (I).
Description
Technical Field
The application relates to the field of organic light-emitting display, in particular to a compound, an electron transport material, an organic electroluminescent device and a display device.
Background
Electroluminescence (EL) refers to a phenomenon in which a light emitting material emits light when excited by current and voltage under the action of an electric field, and is a light emitting process in which electric energy is directly converted into light energy. The organic electroluminescent display (hereinafter referred to as OLED) has a series of advantages of self-luminescence, low-voltage dc driving, full curing, wide viewing angle, light weight, simple composition and process, etc., and compared with the liquid crystal display, the organic electroluminescent display does not need a backlight source, and has a large viewing angle, low power, a response speed 1000 times that of the liquid crystal display, and a manufacturing cost lower than that of the liquid crystal display with the same resolution. Therefore, the organic electroluminescent device has very wide application prospect.
With the continuous advance of the OLED technology in the two fields of lighting and display, people pay more attention to the research on efficient organic materials affecting the performance of OLED devices, and an organic electroluminescent device with good efficiency and long service life is generally the result of the optimized matching of device structures and various organic materials, which provides great opportunities and challenges for chemists to design and develop functional materials with various structures.
Organic electroluminescent materials have many advantages over inorganic luminescent materials, such as: the processing performance is good, and flexible display and large-area display can be realized by forming a film on any substrate by an evaporation or spin coating method; the optical property, the electrical property, the stability and the like of the material can be adjusted by changing the structure of the molecule, and the selection of the material has a large space. In the most common OLED device structures, the following classes of organic materials are typically included: hole injection materials, hole transport materials, electron transport materials, and light emitting materials (dyes or doped guest materials) and corresponding host materials of each color. Among them, the electron transport material, as an important functional material, has a direct influence on the mobility of electrons and ultimately affects the light emitting efficiency of the OLED.
Disclosure of Invention
An object of embodiments of the present application is to provide a compound for an electron transport material.
In a first aspect, the present application provides a compound having the structure of formula (I):
wherein the content of the first and second substances,
Ar1and Ar2Each independently selected from C unsubstituted or substituted by Ra6-C30Aryl of (2), C unsubstituted or substituted by Ra3-C30The heteroaryl group of (a);
X1-X3、Y1-Y5each independently selected from CR1Or N, and X1-X3At least one of them is selected from N, Y1-Y5At least one of (A) and (B) is selected from N, R1Each independently selected from hydrogen, deuterium, cyano, C1-C6Alkyl, unsubstituted or Ra-substituted C6-C30Aryl of (2), C unsubstituted or substituted by Ra3-C30Heteroaryl of, adjacent to R1Can be connected into a ring;
r is selected from hydrogen, deuterium, C unsubstituted or substituted by Ra6-C30Aryl of (2), C unsubstituted or substituted by Ra3-C30The heteroaryl group of (a);
L1-L3each independently selected from the group consisting of a single bond, C unsubstituted or substituted by Ra6-C30Arylene of, unsubstituted or substituted by Ra C3-C30The heteroarylene group of (a);
each heteroatom in the heteroaryl or the heteroarylene is independently selected from O, S, N;
the substituents Ra of each group are each independently selected from deuterium, halogen, nitro, cyano, C1-C4Alkyl, phenyl, biphenyl, terphenyl, naphthyl.
In a second aspect, the present application provides an electron transport material comprising at least one of the compounds provided herein.
In a third aspect, the present application provides an organic electroluminescent device comprising at least one of the electron transport materials provided herein.
A fourth aspect of the present application provides a display apparatus comprising the organic electroluminescent device provided herein.
The compound provided by the application has a parent structure of s-triphenylphenanthrene substituted triazine, has high bond energy among atoms, has good thermal stability, is favorable for solid-state accumulation among molecules, and has strong transition capability of electrons. When the organic electroluminescent device is used as an electron transport material, the organic electroluminescent device has a proper energy level with the adjacent layers, and is beneficial to the injection and migration of electrons, so that the driving voltage of the organic electroluminescent device is effectively reduced, the current efficiency of the organic electroluminescent device is improved, and the service life of the organic electroluminescent device is prolonged. The organic electroluminescent device comprises the compound as an electron transport material, so that the driving voltage of the electroluminescent device can be effectively reduced, the current efficiency of the organic electroluminescent device can be improved, and the service life of the organic electroluminescent device can be prolonged. The display device provided by the application comprises the organic electroluminescent device provided by the application, and has an excellent display effect.
Of course, not all advantages described above need to be achieved at the same time in the practice of any one product or method of the present application.
Drawings
In order to more clearly illustrate the embodiments of the present application or the technical solutions in the prior art, the drawings needed to be used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only one embodiment of the present application, and other embodiments can be obtained by those skilled in the art according to the drawings.
Fig. 1 is a schematic structural view of a typical organic electroluminescent device.
Detailed Description
The technical solutions in the embodiments of the present application will be clearly and completely described below with reference to the drawings in the embodiments of the present application, and it is obvious that the described embodiments are only a part of the embodiments of the present application, and not all of the embodiments. All other embodiments that can be derived by one of ordinary skill in the art from the description herein are intended to be within the scope of the present disclosure.
In a first aspect, the present application provides a compound having the structure of formula (I):
wherein the content of the first and second substances,
Ar1and Ar2Each independently selected from C unsubstituted or substituted by Ra6-C30Aryl of (2), C unsubstituted or substituted by Ra3-C30The heteroaryl group of (a);
X1-X3、Y1-Y5each independently selected from CR1Or N, and X1-X3At least one of them is selected from N, Y1-Y5At least one of (A) and (B) is selected from N, R1Each independently selected from hydrogen, deuterium, cyano, C1-C6Alkyl of (2), unsubstituted or substituted by RaSubstituted C6-C30Aryl of (2), C unsubstituted or substituted by Ra3-C30Heteroaryl of, adjacent to R1Can be connected into a ring;
r is selected from hydrogen, deuterium, C unsubstituted or substituted by Ra6-C30Aryl of (2), C unsubstituted or substituted by Ra3-C30The heteroaryl group of (a);
L1-L3each independently selected from the group consisting of a single bond, C unsubstituted or substituted by Ra6-C30Arylene of, unsubstituted or substituted by Ra C3-C30The heteroarylene group of (a);
each heteroatom in the heteroaryl or the heteroarylene is independently selected from O, S, N;
the substituents Ra of each group are each independently selected from deuterium, halogen, nitro, cyano, C1-C4Alkyl, phenyl, biphenyl, terphenyl, naphthyl.
The compound provided by the application has a parent structure of s-triphenylphenanthrene substituted triazine, has high bond energy among atoms, has good thermal stability, is favorable for solid-state accumulation among molecules, and has strong transition capability of electrons. In addition, the compound provided by the application has the advantages of simple and feasible preparation process and easily obtained raw materials, and is suitable for industrial production.
Preferably, Ar1And Ar2Each independently selected from C unsubstituted or substituted by Ra6-C18Aryl of (2), C unsubstituted or substituted by Ra3-C18The heteroaryl group of (a);
preferably, R1Each independently selected from hydrogen, deuterium, cyano, C1-C6Alkyl, unsubstituted or Ra-substituted C6-C18Aryl of (2), C unsubstituted or substituted by Ra3-C18The heteroaryl group of (a);
preferably, R is selected from hydrogen, deuterium, C unsubstituted or substituted by Ra6-C18Aryl of (2), C unsubstituted or substituted by Ra3-C18The heteroaryl group of (a);
preferably, L1-L3Each independently of the otherIs selected from single bond, C unsubstituted or substituted by Ra6-C18Arylene of, unsubstituted or substituted by Ra C3-C18The heteroarylene group of (1).
More preferably, Ar1And Ar2Each independently selected from the following unsubstituted or substituted with Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furanyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, arylamino, carbazolyl.
More preferably, R1Each independently selected from hydrogen, deuterium, cyano, methyl, ethyl, cyclopentyl, cyclohexyl, the following groups unsubstituted or substituted with Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furanyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, arylamino, carbazolyl.
More preferably, R is selected from hydrogen, deuterium, the following groups unsubstituted or substituted by Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furanyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, arylamino, carbazolyl.
More preferably, L1-L3Each independently selected from the group consisting of a single bond and an unsubstitutedAnd (b) a subunit of the following compound substituted or unsubstituted with Ra: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, pyridine, pyridazine, pyrimidine, pyrazine, quinoline, isoquinoline, quinazoline, quinoxaline, cinnoline, naphthyridine, triazine, pyridopyrazine, furan, benzofuran, dibenzofuran, aza-dibenzofuran, thienylene, benzothiophene, dibenzothiophene, aza-dibenzothiophene, 9-dimethylfluorene, spirofluorene, arylamine, carbazole.
For example, the aforementioned compound is selected from any of the following structures a1-a 40:
in a second aspect, the present application provides an electron transport material comprising at least one of the compounds provided herein.
When the electron transport material is applied to the electron transport layer, the electron transport material has a proper energy level with the adjacent layers, and is beneficial to the injection and migration of electrons, so that the driving voltage of an organic electroluminescent device is effectively reduced, the current efficiency of the organic electroluminescent device is improved, and the service life of the organic electroluminescent device is prolonged.
A third aspect of the present application provides an organic electroluminescent device comprising at least one of the electron transport materials provided herein. Therefore, the organic electroluminescent device provided by the application has low driving voltage, high luminous efficiency and long service life.
In the present application, there is no particular limitation on the kind and structure of the organic electroluminescent device, and there may be various types and structures of organic electroluminescent devices known in the art as long as at least one of the electron transport materials provided herein may be used.
The organic electroluminescent device of the present application may be a light-emitting device having a top emission structure, and examples thereof include a light-emitting device comprising an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a transparent or translucent cathode in this order on a substrate.
The organic electroluminescent device of the present application may be a light-emitting device having a bottom emission structure, and may include a structure in which a transparent or translucent anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode are sequentially provided on a substrate.
The organic electroluminescent device of the present application may be a light-emitting device having a double-sided light-emitting structure, and may include a structure in which a transparent or translucent anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a transparent or translucent cathode are sequentially provided on a substrate.
In addition, an electron blocking layer may be provided between the hole transport layer and the light emitting layer, a hole blocking layer may be provided between the light emitting layer and the electron transport layer, and a light extraction layer may be provided on the transparent electrode on the light outgoing side. However, the structure of the organic electroluminescent device of the present application is not limited to the above-described specific structure, and the above-described layers may be omitted or added if necessary. The thickness of each layer is not particularly limited as long as the object of the present invention can be achieved. For example, the organic electroluminescent device may include an anode made of metal, a hole injection layer (5nm to 20nm), a hole transport layer (80nm to 140nm), an electron blocking layer (5nm to 20nm), a light emitting layer (150nm to 400nm), a hole blocking layer (5nm to 20nm), an electron transport layer (300nm to 800nm), an electron injection layer (5nm to 20nm), a transparent or semitransparent cathode, and a light extraction layer (50nm to 90nm) in this order on a substrate.
Fig. 1 shows a schematic diagram of a typical organic electroluminescent device, in which a substrate 1, a reflective anode electrode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 5, an electron transport layer 6, an electron injection layer 7, and a cathode electrode 8 are sequentially disposed from bottom to top.
It is to be understood that fig. 1 schematically illustrates the structure of a typical organic electroluminescent device, and the present application is not limited to this structure, and the electron transport material of the present application may be used in any type of organic electroluminescent device.
In the organic electroluminescent device of the present application, various materials used for the layers in the prior art may be used for the layers, except that the electron transport layer contains the electron transport material provided herein.
For convenience, the organic electroluminescent device of the present application is described below with reference to fig. 1, but this is not meant to limit the scope of the present application in any way. It is understood that all organic electroluminescent devices capable of using the electron transport material of the present application are within the scope of the present application.
In the present application, the material of the substrate 1 is not particularly limited, and conventional substrates used in organic electroluminescent devices in the related art, for example, glass, polymer materials, glass with Thin Film Transistor (TFT) components, polymer materials, and the like, may be used.
In the present application, the material of the reflective anode electrode 2 is not particularly limited, and may be selected from Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO) known in the art2) The transparent conductive material such as zinc oxide (ZnO) or Low Temperature Polysilicon (LTPS) may be selected from metal materials such as silver and its alloy, aluminum and its alloy, organic conductive materials such as poly (3, 4-ethylenedioxythiophene) (PEDOT), and a multilayer structure of the above materials.
In the present application, the material of the hole injection layer 3 is not particularly limited, and a hole injection layer material known in the art, for example, a Hole Transport Material (HTM) is selected as the hole injection material.
In the present application, the hole injection layer 3 may further include a p-type dopant, the kind of the p-type dopant is not particularly limited, and various p-type dopants known in the art may be used, for example, the p-type dopant may be selected from at least one of the following p-1 to p-3 compounds:
in the present application, the amount of the p-type dopant is not particularly limited and may be an amount well known to those skilled in the art.
In the present application, the material of the hole transport layer 4 is not particularly limited, and may be made using a Hole Transport Material (HTM) known in the art. The number of layers of the hole transport layer 4 is not particularly limited, and may be adjusted as needed as long as it satisfies the object of the present application, for example, 1 layer, 2 layers, 3 layers, 4 layers or more.
For example, the material for the hole injection layer and the material for the hole transport layer may each be independently selected from, but not limited to, at least one of the following HT-1 to HT-31 compounds:
in the present application, the light emitting layer 5 may include a blue light emitting layer, a green light emitting layer, or a red light emitting layer, and the light emitting material in the light emitting layer 5 is not particularly limited, and various light emitting materials known to those skilled in the art may be used, for example, the light emitting material may include a host material and a guest material. In the present application, the amounts of the host material and the guest material are not particularly limited, and may be those known to those skilled in the art.
In the present application, the host material of the red light emitting layer is not particularly limited, and at least one of the host materials of the red light emitting layer known in the art may be used. For example, it may be selected from, but not limited to, at least one of the following RH-1 to RH-13 compounds, and GPH-1 to GPH-80 compounds:
in the present application, the host material of the green light emitting layer is not particularly limited, and at least one of the host materials of the green light emitting layer known in the art may be used. For example, it may be selected from, but not limited to, at least one of the aforementioned GPH-1 to GPH-80 compounds.
In the present application, the host material of the blue light emitting layer is not particularly limited, and at least one of the host materials of the blue light emitting layer known in the art may be used. For example, at least one compound selected from, but not limited to, the following BH-1 to BH-36 compounds:
in the present application, the guest material of the red light emitting layer is not particularly limited, and at least one of the guest materials of the red light emitting layer known in the art may be used. For example, at least one of the following RPD-1 to RPD-28 compounds may be selected, but is not limited to:
in the present application, the guest material of the green light emitting layer is not particularly limited, and at least one of the guest materials of the green light emitting layer known in the art may be used. For example, at least one of the following GD 01-GD 04 compounds may be selected, but is not limited to:
in the present application, the guest material of the blue light emitting layer is not particularly limited, and at least one of the guest materials of the blue light emitting layer known in the art may be used. For example, at least one of the following BD01 to BD04 compounds may be selected from, but not limited to:
in the present application, the electron transport layer 6 may contain at least one of the electron transport materials of the present application, and may also contain a combination of at least one of the electron transport materials of the present application and at least one of the following known electron transport materials.
For example, known electron transport materials may be selected from, but are not limited to, at least one of the following ET-1 to ET-57 compounds:
in the present application, the electron transport layer 6 may further include an n-type dopant, the kind of the n-type dopant is not particularly limited, and various n-type dopants known in the art may be employed, for example, the following n-type dopants may be employed:
in the present application, the amount of the n-type dopant is not particularly limited and may be an amount well known to those skilled in the art.
In the present application, the material of the electron injection layer 7 is not particularly limited, and electron injection materials known in the art may be used, and for example, may include, but are not limited to, LiQ, LiF, NaCl, CsF, Li in the prior art2O、Cs2CO3At least one of BaO, Na, Li, Ca and the like.
In the present application, the material of the cathode electrode 8 is not particularly limited, and may be selected from, but not limited to, magnesium-silver mixture, magnesium-aluminum mixture, metal such as LiF/Al, ITO, Al, etc., metal mixture, oxide, etc.
The fourth aspect of the present application provides a display device comprising the organic electroluminescent device provided by the present application, having excellent display effect. The display device includes, but is not limited to, a display, a television, a mobile communication terminal, a tablet computer, and the like.
The method for preparing the organic electroluminescent device of the present application is not particularly limited, and any method known in the art may be used, for example, the present application may be prepared by the following preparation method:
(1) cleaning a reflective anode electrode 2 on an OLED device substrate 1 for top emission, respectively carrying out steps of medicinal washing, water washing, hairbrush, high-pressure water washing, air knife and the like in a cleaning machine, and then carrying out heat treatment;
(2) vacuum evaporating a hole injection material on the reflecting anode electrode 2 to form a hole injection layer 3, wherein the hole injection layer 3 contains a main body material and a p-type dopant;
(3) vacuum evaporating a hole transport material on the hole injection layer 3 to form a hole transport layer 4;
(4) a luminescent layer 5 is evaporated on the hole transport layer 4 in vacuum, wherein the luminescent layer 5 comprises a host material and a guest material;
(5) vacuum evaporating an electron transport material on the luminescent layer 5 to form an electron transport layer 6;
(6) vacuum evaporating an electron injection material on the electron transport layer 6 to form an electron injection layer 7;
(7) a cathode material is vacuum-deposited on the electron injection layer 7 as a cathode electrode 8.
The above description has been made only of the structure of a typical organic electroluminescent device and a method for manufacturing the same, and it should be understood that the present application is not limited to this structure. The electron transport material of the present application can be used for an organic electroluminescent device of any structure, and the organic electroluminescent device can be manufactured by any manufacturing method known in the art.
The method for synthesizing the compound of the present application is not particularly limited, and the synthesis can be carried out by any method known to those skilled in the art. The following illustrates the synthesis of the compounds of the present application.
Synthetic examples
Synthesis example 1: synthesis of Compound A1
Into a reaction flask were charged 100mmol of 3-bromo-5-chlorophenol, 100mmol of 3-pyridineboronic acid, 41.4g of potassium carbonate (300mmol), 800ml Tetrahydrofuran (THF) and 200ml water, and 1 mol% tetrakis (triphenylphosphine) palladium (Pd (PPh) added3)4). The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M1. Wherein, Pd (PPh)3)4The amount of (A) added was 1 mol% based on the amount of 3-bromo-5-chlorophenol.
Into a reaction flask were charged 100mmol of M1, 100mmol of 1-naphthalene boronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M2. Wherein, Pd (PPh)3)4Was added in an amount of 1 mol% based on M1.
Adding 100mmol of M2, 300ml of dichloromethane and 30ml of triethylamine into a reaction bottle, cooling to 0 ℃, dropwise adding 100mmol of trifluoromethanesulfonic anhydride, and reacting at normal temperature for 12 h. After the reaction is finished, water is added, a solid is precipitated and filtered, and an intermediate M3 is obtained, wherein a group TfO in M3 is a triflate group.
Into a reaction flask were charged 100mmol of 2-chloro-4-phenyl-6- (9-phenanthryl) triazine, 100mmol of 4-bromobenzeneboronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M4. Wherein, Pd (PPh)3)4The amount of (b) added was 1 mol% based on 2-chloro-4-phenyl-6- (9-phenanthryl) triazine.
100mmol of M4, 110mmol of pinacol diboron, 29.4g of potassium acetate (300mmol), 800ml of dioxane and 1 mol% of dichloro [1,1' -bis (diphenylphosphino) ferrocene are introduced into a reaction flask]Palladium (Pd (dppf) Cl2). The reaction was carried out at 100 ℃ for 12 h. After the reaction is finishedAfter completion of the reaction, the reaction was stopped, and the reaction was cooled to room temperature, water was added, the organic phase was separated, concentrated to give a white solid, filtered, washed with water, and the obtained solid was recrystallized from toluene to obtain white powder M5. Wherein Pd (dppf) Cl2Was added in an amount of 1 mol% based on M4.
Into a reaction flask were charged 100mmol of M3, 100mmol of M5, 41.4g potassium carbonate (300mmol), 800ml THF and 200ml water, and 1 mol% Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder a 1. Wherein, Pd (PPh)3)4Was added in an amount of 1 mol% based on M3.
1H NMR(400MHz,Chloroform)δ9.24(s,1H),9.01(d,J＝12.0Hz,2H),8.84(s,1H),8.77(d,J＝10.0Hz,2H),8.50(s,1H),8.36(t,J＝12.4Hz,4H),8.23(s,1H),8.20–8.14(m,6H),8.12–7.72(m,4H),7.78(d,J＝8.0Hz,2H),7.78(d,J＝8.4Hz,2H),7.69(d,J＝10.0Hz,3H),7.62(d,J＝8.0Hz,2H),7.48(d,J＝12.0Hz,4H),7.40(s,1H),7.34(s,1H),7.25(s,1H).
Synthesis example 2: synthesis of Compound A9
Into a reaction flask were charged 100mmol of 3-bromo-5-chlorophenol, 100mmol of 3-pyridineboronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M1. Wherein, Pd (PPh)3)4The amount of (A) added was 1 mol% based on the amount of 3-bromo-5-chlorophenol.
100mmol of M1, 110mmol of pinacol diborate, 29.4g of potassium acetate (300mmol) and 800ml of dioxygen were placed in a reaction flaskHexacyclic ring, and 1 mol% Pd (dppf) Cl2. The reaction was carried out at 100 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, the organic phase was separated, concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M2. Wherein Pd (dppf) Cl2Was added in an amount of 1 mol% based on M1.
Into a reaction flask were charged 100mmol of M2, 100mmol of 2-chloro-4-phenylquinazoline, 41.4g potassium carbonate (300mmol), 800ml THF and 200ml water, and 1 mol% Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M3. Wherein, Pd (PPh)3)4Was added in an amount of 1 mol% based on M2.
Adding 100mmol of M3, 300ml of dichloromethane and 30ml of triethylamine into a reaction bottle, cooling to 0 ℃, dropwise adding 100mmol of trifluoromethanesulfonic anhydride, and reacting at normal temperature for 12 h. After the reaction is finished, water is added, a solid is precipitated and filtered, and an intermediate M4 is obtained, wherein a group TfO in M4 is a triflate group.
100mmol of M4, 110mmol of pinacol diborate, 29.4g of potassium acetate (300mmol), 800ml of dioxane and 1 mol% of Pd (dppf) Cl were charged in a reaction flask2. The reaction was carried out at 100 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, the organic phase was separated, concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M5. Wherein Pd (dppf) Cl2Was added in an amount of 1 mol% based on M4.
Into a reaction flask were charged 100mmol of 2-chloro-4- (4-biphenyl) -6- (9-phenanthryl) triazine, 100mmol of M5, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. Stopping reaction after reaction, cooling the reactant to room temperature, adding water, concentrating the organic phase to obtain white solid, filtering, washing with water, and collecting the solidBenzene was purified by recrystallization to give a white powder a 9. Wherein, Pd (PPh)3)4Was added in an amount of 1 mol% based on M5.
1H NMR(400MHz,Chloroform)δ9.24(s,1H),9.08(s,1H),8.77(d,J＝10.0Hz,2H),8.69–8.68(m,2H),8.63(s,1H),8.44(s,1H),8.41(d,J＝12.4Hz,3H),8.33-8.17(m,6H),8.13(s,1H),7.92–7.73(m,6H),7.72–7.55(m,4H),7.54(s,1H),7.45(dd,J＝12.8,8.0Hz,4H),7.25(s,1H).
Synthetic example 3: synthesis of Compound A13
Into a reaction flask were charged 100mmol of 3-bromo-5-chlorophenol, 100mmol of 2-naphthoic acid, 41.4g of potassium carbonate (500mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M1. Wherein, Pd (PPh)3)4The amount of (A) added was 1 mol% based on the amount of 3-bromo-5-chlorophenol.
Into a reaction flask were charged 100mmol of M1, 100mmol of 4- (3-pyridyl) phenylboronic acid, 41.4g of potassium carbonate (500mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M2. Wherein, Pd (PPh)3)4Was added in an amount of 1 mol% based on M1.
Adding 100mmol of M2, 300ml of dichloromethane and 30ml of triethylamine into a reaction bottle, cooling to 0 ℃, dropwise adding 100mmol of trifluoromethanesulfonic anhydride, and reacting at normal temperature for 12 h. After the reaction is finished, water is added, a solid is precipitated and filtered, and an intermediate M3 is obtained, wherein a group TfO in M3 is a triflate group.
100mmol of M3, 110mmol of pinacol diborate, 29.4g of potassium acetate (300mmol), 800ml of dioxane and 1 mol% of Pd (dppf) Cl were charged in a reaction flask2. The reaction was carried out at 100 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, the organic phase was separated, concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M4. Wherein Pd (dppf) Cl2Was added in an amount of 1 mol% based on M3.
Into a reaction flask were charged 100mmol of 9-bromophenanthrene, 100mmol of phenylboronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M5. Wherein, Pd (PPh)3)4The amount of the compound (A) is 1 mol% of the 9-bromophenanthrene.
100mmol of M5 and 300ml of dichloromethane are added into a reaction bottle, the temperature is reduced to 0 ℃, 100mmol of N-bromosuccinimide (NBS) is added in batches, and the reaction is carried out for 12 hours at normal temperature. After the reaction, water was added to precipitate a solid, which was then filtered to obtain intermediate M6.
100mmol of M6, 110mmol of pinacol diborate, 29.4g of potassium acetate (300mmol), 800ml of dioxane and 1 mol% of Pd (dppf) Cl were charged in a reaction flask2. The reaction was carried out at 100 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, the organic phase was separated, concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M7. Wherein Pd (dppf) Cl2Was added in an amount of 1 mol% based on M6.
Into a reaction flask were charged 100mmol of 2, 6-dibromo-4-chloropyridine, 100mmol of phenylboronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. Stopping reaction after the reaction is finished, cooling the reactant to room temperature, adding water, and concentrating an organic phase to obtain the compoundWhite solid was obtained, filtered and washed with water, and the obtained solid was purified by recrystallization from toluene to obtain white powder M8. Wherein, Pd (PPh)3)4The amount of (A) to be added was 1 mol% based on the amount of 2, 6-dibromo-4-chloropyridine.
Into a reaction flask were charged 100mmol of M7, 100mmol of M8, 41.4g potassium carbonate (300mmol), 800ml THF and 200ml water, and 1 mol% Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M9. Wherein, Pd (PPh)3)4Was added in an amount of 1 mol% based on M7.
Into a reaction flask were charged 100mmol of M4, 100mmol of M9, 41.4g potassium carbonate (300mmol), 800ml THF and 200ml water, and 1 mol% Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder a 13. Wherein, Pd (PPh)3)4Was added in an amount of 1 mol% based on M4.
1H NMR(400MHz,Chloroform)δ9.24(s,1H),9.08(s,2H),8.70(s,1H),8.33(s,1H),8.28(t,J＝8.8Hz,4H),8.20(s,2H),8.16(d,J＝12.8Hz,4H),8.20–7.80(m,7H),7.70(s,1H),7.68–7.60(m,6H),7.60–7.48(m,8H),7.47(s,1H),7.39(d,J＝12.0Hz,2H),7.25(s,1H).
Synthetic example 4: synthesis of Compound A17
Into a reaction flask were charged 100mmol of 3-bromo-5-chlorophenol, 100mmol of 4-pyridineboronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. Stopping reaction after the reaction is finished, cooling the reactant to room temperature, adding water, and obtaining an organic phaseConcentration gave a white solid, which was filtered and washed with water, and the resulting solid was purified by recrystallization from toluene to give white powder M1. Wherein, Pd (PPh)3)4The amount of (A) added was 1 mol% based on the amount of 3-bromo-5-chlorophenol.
Into a reaction flask were charged 100mmol of M1, 100mmol of 3-cyanophenylboronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M2. Wherein, Pd (PPh)3)4Was added in an amount of 1 mol% based on M1.
Adding 100mmol of M2, 300ml of dichloromethane and 30ml of triethylamine into a reaction bottle, cooling to 0 ℃, dropwise adding 100mmol of trifluoromethanesulfonic anhydride, and reacting at normal temperature for 12 h. After the reaction is finished, water is added, a solid is precipitated and filtered, and an intermediate M3 is obtained, wherein a group TfO in M3 is a triflate group.
100mmol of M3, 110mmol of pinacol diborate, 29.4g of potassium acetate (300mmol), 800ml of dioxane and 1 mol% of Pd (dppf) Cl were charged in a reaction flask2. The reaction was carried out at 100 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, the organic phase was separated, concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M4. Wherein Pd (dppf) Cl2Was added in an amount of 1 mol% based on M3.
A reaction flask was charged with 100mmol of 9- (4-bromophenyl) phenanthrene, 110mmol of pinacol diboron, 29.4g of potassium acetate (300mmol), 800ml of dioxane, and 1 mol% Pd (dppf) Cl2. The reaction was carried out at 100 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, the organic phase was separated, concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M5. Wherein Pd (dppf) Cl2Is added in an amount of 1 mol% based on 9- (4-bromophenyl) phenanthrene.
Into a reaction flask were charged 100mmol of M5, 100mmol of 2, 4-dichloro-6-phenyltriazine, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M6. Wherein, Pd (PPh)3)4Was added in an amount of 1 mol% based on M5.
Into a reaction flask were charged 100mmol of M4, 100mmol of M6, 41.4g potassium carbonate (300mmol), 800ml THF and 200ml water, and 1 mol% Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder a 17. Wherein, Pd (PPh)3)4Was added in an amount of 1 mol% based on M4.
1H NMR(400MHz,Chloroform)δ9.08(s,1H),8.78(d,J＝12.0Hz,3H),8.44(d,J＝8.0Hz,2H),8.36(s,1H),8.29–8.20(m,3H),8.20(s,1H),7.85(dd,J＝10.0,8.0Hz,4H),7.74–7.72(m,3H),7.72–7.66(m,4H),7.63(d,J＝8.0Hz,2H),7.50(s,1H),7.25(s,1H).
Synthesis example 5: synthesis of Compound A22
Into a reaction flask were charged 100mmol of 3-bromo-5-chloroiodobenzene, 100mmol of 3-pyridineboronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M1. Wherein, Pd (PPh)3)4The amount of addition of (A) is 1 mol% of 3-bromo-5-chloroiodobenzene.
Into a reaction flask were charged 100mmol of M1, 100mmol of phenylboronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M2. Wherein, Pd (PPh)3)4Was added in an amount of 1 mol% based on M1.
100mmol of M2, 110mmol of pinacol diborate, 29.4g of potassium acetate (300mmol), 800ml of dioxane and 1 mol% of Pd (dppf) Cl were charged in a reaction flask2. The reaction was carried out at 100 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, the organic phase was separated, concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M3. Wherein Pd (dppf) Cl2Was added in an amount of 1 mol% based on M2.
Into a reaction flask were charged 100mmol of 2-bromo-4-chlorophenol, 100mmol of 2-fluorobenzeneboronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M4. Wherein, Pd (PPh)3)4The amount of (A) added was 1 mol% based on 2-bromo-4-chlorophenol.
400ml of glacial acetic acid and 100ml of water are added into a 1L three-neck flask provided with a stirrer, nitrogen is bubbled for 15min, 100mmol of M4, 100mmol of iodine and 300mmol of potassium iodate are sequentially added into the reaction solution, and the mixture is stirred at normal temperature and reacted for 12 h. 400ml of methylene chloride was added to the reaction solution with stirring, and stirred for 30min, followed by liquid separation, and the organic phases were combined and rotary-evaporated to dryness to obtain M5 as a white powder.
To a reaction flask were added 100mmol of M5, 41.4g potassium carbonate (300mmol), 800ml of N-methylpyrrolidone (NMP). The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added to obtain a white solid, which was filtered and washed with water, and the obtained solid was purified by recrystallization from toluene to obtain white powder M6.
Into a reaction flask were charged 100mmol of M3, 100mmol of M6, 41.4g potassium carbonate (300mmol), 800ml THF and 200ml water, and 1 mol% Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M7. Wherein, Pd (PPh)3)4Was added in an amount of 1 mol% based on M3.
100mmol of M7, 110mmol of pinacol diborate, 29.4g of potassium acetate (300mmol), 800ml of dioxane and 1 mol% of Pd (dppf) Cl were charged in a reaction flask2. The reaction was carried out at 100 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction was cooled to room temperature, water was added, the organic phase was separated, concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder M8. Wherein Pd (dppf) Cl2Was added in an amount of 1 mol% based on M7.
Into a reaction flask were added 100mmol of M8, 100mmol of 2-chloro-4-phenyl-6- (9-phenanthryl) -triazine, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, the organic phase was concentrated to obtain a white solid, which was filtered and washed with water, and the obtained solid was recrystallized from toluene to obtain a white powder a 22. Wherein, Pd (PPh)3)4Was added in an amount of 1 mol% based on M8.
1H NMR(400MHz,Chloroform)δ9.24(s,1H),9.08(s,1H),8.75(t,J＝12.0Hz,3H),8.59(s,1H),8.49–8.22(m,6H),8.18(d,J＝10.8Hz,2H),7.98-7.75(m,4H),7.69(d,J＝10.0Hz,2H),7.63(d,J＝8.0Hz,2H),7.54(s,1H),7.52–7.45(m,6H),7.40(d,J＝10.0Hz,2H),7.31(s,1H).
Other compounds of the present application can be synthesized by selecting suitable raw materials according to the idea of synthesis examples 1 to 5, and any other suitable methods and raw materials can be selected for synthesis.
Example 1
Carrying out ultrasonic treatment on the glass plate coated with the ITO transparent conductive layer in a commercial cleaning agent, washing in deionized water, carrying out ultrasonic oil removal in an acetone-ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy solar beams;
then, the glass substrate with the anode is placed in a vacuum chamber and is vacuumized to be less than 10 DEG-5In the torr, a hole injection layer is vacuum evaporated on the anode layer film, the material of the hole injection layer is a hole transport material HT-11 and a p-type dopant (p-1) with the mass ratio of 3%, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10 nm;
then, vacuum evaporating a hole transport material HT-5 on the hole injection layer to be used as a hole transport layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 80 nm;
then, a light-emitting layer is evaporated on the hole transport layer in vacuum, the light-emitting layer comprises a host material GHP-16 and a guest material RPD-1, evaporation is carried out by a multi-source co-evaporation method, the evaporation rate of the host material GHP-16 is adjusted to be 0.1nm/s, the evaporation rate of the guest material RPD-1 is 3% of the evaporation rate of the host material GHP-16, and the total thickness of the evaporation film is 30 nm;
then, an electron transport material A1 is vacuum-evaporated on the luminescent layer to be used as an electron transport layer, the evaporation rate is 0.1nm/s, and the evaporation film thickness is 30 nm;
then, LiF with the thickness of 0.5nm is evaporated on the electron transport layer in vacuum to be used as an electron injection layer, and the evaporation rate is 0.1 nm/s;
and finally, evaporating Al with the thickness of 150nm on the electron injection layer to be used as a cathode, wherein the evaporation rate is 1 nm/s.
The organic electroluminescent device of the present embodiment emits red light.
Examples 2 to 5
The procedure was as in example 1 except that A1 was replaced with A9, A13, A17 and A22, respectively.
Example 6
The procedure is as in example 1, except that GPH-44 is used in place of GHP-16 and GD04 is used in place of RPD-1. The organic electroluminescent device of the present embodiment emits green light.
Example 7
The procedure of example 1 was repeated, except that the compound BH-1 was used in place of GHP-16 and the compound BD01 was used in place of RPD-1. The organic electroluminescent device of the present embodiment emits blue light.
Comparative example 1
The procedure was as in example 1, except that compound ET-2 was used in place of A1.
Comparative example 2
The procedure was as in example 1 except that A1 was replaced with Compound R-1 represented by the following formula.
Comparative example 3
The procedure was as in example 6, except that compound ET-2 was used in place of A1.
Comparative example 4
The procedure was as in example 7, except that compound ET-2 was used in place of A1.
The performance test method of the organic electroluminescent device comprises the following steps:
the driving voltage, current efficiency and lifetime of the organic electroluminescent devices prepared in examples 1 to 7 and comparative examples 1 to 4 were measured at the same luminance using a digital source meter and a luminance meter, as follows:
< Driving Voltage and Current efficiency test >
(1) Red light device: the voltage was raised at a rate of 0.1V per second, as determined when the luminance of the organic electroluminescent device reached 5000cd/m2The current density is measured at the same time as the driving voltage; the ratio of the luminance to the current density is the current efficiency.
(2) Green light device: the brightness of the organic electroluminescent device was measured by increasing the voltage at a rate of 0.1V per secondTo 10000cd/m2The current density is measured at the same time as the driving voltage; the ratio of the luminance to the current density is the current efficiency.
(3) Blue light device: the voltage was raised at a rate of 0.1V per second, as determined when the luminance of the organic electroluminescent device reached 1000cd/m2The current density is measured at the same time as the driving voltage; the ratio of the luminance to the current density is the current efficiency.
< Life test of LT95 >
(1) Red light device: using a luminance meter at 5000cd/m2The luminance drop of the organic electroluminescent device was measured to be 4750cd/m by maintaining a constant current at luminance2Time in hours.
(2) Green light device: using a luminance meter at 10000cd/m2The luminance drop of the organic electroluminescent device was measured to be 9500cd/m by maintaining a constant current at luminance2Time in hours.
(3) Blue light device: using a luminance meter at 1000cd/m2The luminance drop of the organic electroluminescent device was measured to 950cd/m by maintaining a constant current at luminance2Time in hours.
TABLE 1 Performance results of organic electroluminescent devices of examples and comparative examples
As can be seen from the data in table 1, the use of the compounds a1, a9, a13, a17, a22 provided in the present application as electron transport materials for organic electroluminescent devices in examples 1 to 7 enables lower driving voltages, higher current efficiencies, and longer life of LT95 for red, green, and blue light-emitting devices at the same luminance, as compared to the use of known materials in the prior art as electron transport materials for organic electroluminescent devices in comparative examples 1 to 4. Therefore, the compound is applied to an organic electroluminescent device as an electron transport material, and can effectively reduce the driving voltage of the organic electroluminescent device, improve the current efficiency of the organic electroluminescent device and prolong the service life of the organic electroluminescent device.
The above description is only for the preferred embodiment of the present application and is not intended to limit the scope of the present application. Any modification, equivalent replacement, improvement and the like made within the spirit and principle of the present application are included in the protection scope of the present application.
Claims (10)
1. A compound having the structure of formula (I):
wherein the content of the first and second substances,
Ar1and Ar2Each independently selected from C unsubstituted or substituted by Ra6-C30Aryl of (2), C unsubstituted or substituted by Ra3-C30The heteroaryl group of (a);
X1-X3、Y1-Y5each independently selected from CR1Or N, and X1-X3At least one of them is selected from N, Y1-Y5At least one of (A) and (B) is selected from N, R1Each independently selected from hydrogen, deuterium, cyano, C1-C6Alkyl, unsubstituted or Ra-substituted C6-C30Aryl of (2), C unsubstituted or substituted by Ra3-C30Heteroaryl of, adjacent to R1Can be connected into a ring;
r is selected from hydrogen, deuterium, C unsubstituted or substituted by Ra6-C30Aryl of (2), C unsubstituted or substituted by Ra3-C30The heteroaryl group of (a);
L1-L3each independently selected from the group consisting of a single bond, C unsubstituted or substituted by Ra6-C30Arylene of, unsubstituted or substituted by Ra C3-C30The heteroarylene group of (a);
each heteroatom in the heteroaryl or the heteroarylene is independently selected from O, S, N;
each radicalThe substituents Ra of the radicals are each independently selected from deuterium, halogen, nitro, cyano, C1-C4Alkyl, phenyl, biphenyl, terphenyl, naphthyl.
2. The compound of claim 1, wherein,
Ar1and Ar2Each independently selected from C unsubstituted or substituted by Ra6-C18Aryl of (2), C unsubstituted or substituted by Ra3-C18The heteroaryl group of (a);
R1each independently selected from hydrogen, deuterium, cyano, C1-C6Alkyl, unsubstituted or Ra-substituted C6-C18Aryl of (2), C unsubstituted or substituted by Ra3-C18The heteroaryl group of (a);
r is selected from hydrogen, deuterium, C unsubstituted or substituted by Ra6-C18Aryl of (2), C unsubstituted or substituted by Ra3-C18The heteroaryl group of (a);
L1-L3each independently selected from the group consisting of a single bond, C unsubstituted or substituted by Ra6-C18Arylene of, unsubstituted or substituted by Ra C3-C18The heteroarylene group of (1).
3. The compound of claim 1, wherein said Ar is1And Ar2Each independently selected from the following unsubstituted or substituted with Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furanyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, arylamino, carbazolyl.
4. The compound of claim 1, wherein R is1Are independently selected fromFrom hydrogen, deuterium, cyano, methyl, ethyl, cyclopentyl, cyclohexyl, the following groups unsubstituted or substituted by Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furanyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, arylamino, carbazolyl.
5. The compound of claim 1, wherein R is selected from hydrogen, deuterium, the following groups unsubstituted or substituted with Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furanyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, arylamino, carbazolyl.
6. The compound of claim 1, wherein said L1-L3Each independently selected from a single bond, a subunit of the following compounds unsubstituted or substituted with Ra: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, pyridine, pyridazine, pyrimidine, pyrazine, quinoline, isoquinoline, quinazoline, quinoxaline, cinnoline, naphthyridine, triazine, pyridopyrazine, furan, benzofuran, dibenzofuran, aza-dibenzofuran, thienylene, benzothiophene, dibenzothiophene, aza-dibenzothiophene, 9-dimethylfluorene, spirofluorene, arylamine, carbazole.
7. The compound according to claim 1, wherein said compound is selected from any one of the following structures a1-a 40:
8. an electron transport material comprising at least one of the compounds of any one of claims 1-7.
9. An organic electroluminescent device comprising at least one of the electron transport materials of claim 8.
10. A display device comprising the organic electroluminescent device according to claim 9.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110496937.2A CN113234010A (en) | 2021-05-07 | 2021-05-07 | Compound, electron transport material, organic electroluminescent device and display device |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110496937.2A CN113234010A (en) | 2021-05-07 | 2021-05-07 | Compound, electron transport material, organic electroluminescent device and display device |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN113234010A true CN113234010A (en) | 2021-08-10 |
Family
ID=77132230
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110496937.2A Pending CN113234010A (en) | 2021-05-07 | 2021-05-07 | Compound, electron transport material, organic electroluminescent device and display device |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113234010A (en) |
Citations (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20100001274A (en) * | 2008-06-26 | 2010-01-06 | 제일모직주식회사 | Organic compound, and organic photoelectric device including the same |
| KR20110049554A (en) * | 2009-11-05 | 2011-05-12 | 엘지디스플레이 주식회사 | Blue color fluorescence compounds and organic light emitting diode comprising thereof |
| WO2011086863A1 (en) * | 2010-01-15 | 2011-07-21 | 富士フイルム株式会社 | Organic electroluminescent element |
| WO2011102586A1 (en) * | 2010-02-22 | 2011-08-25 | 제일모직 주식회사 | Compound for an organic photoelectric device and photoelectric device including same |
| US20140367656A1 (en) * | 2013-06-12 | 2014-12-18 | Samsung Display Co., Ltd. | Organic light-emitting diode |
| KR20150122343A (en) * | 2014-04-23 | 2015-11-02 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| KR20150131998A (en) * | 2014-05-15 | 2015-11-25 | 주식회사 엘지화학 | Hetero-cyclic compound and organic light emitting device comprising the same |
| KR20150140241A (en) * | 2014-06-05 | 2015-12-15 | 주식회사 엘지화학 | Hetero-cyclic compound and organic light emitting device comprising the same |
| KR20160005944A (en) * | 2014-07-08 | 2016-01-18 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| CN106164215A (en) * | 2014-04-04 | 2016-11-23 | 株式会社Lg化学 | Organic luminescent device |
| KR20160149527A (en) * | 2015-06-18 | 2016-12-28 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| CN107531651A (en) * | 2015-06-01 | 2018-01-02 | 株式会社Lg化学 | Heterocyclic compound and the organic luminescent device for including it |
| KR20180061074A (en) * | 2016-11-29 | 2018-06-07 | 주식회사 엘지화학 | Novel hetero-cyclic compound and organic light emitting device comprising the same |
| CN109575001A (en) * | 2017-09-29 | 2019-04-05 | Cmdl有限公司 | 3- dibenzofurans based triazine derivative organic compound and the organic electroluminescence device comprising it |
| CN109705148A (en) * | 2018-12-28 | 2019-05-03 | 武汉天马微电子有限公司 | Aromatic cycle compound, display panel and display device |
| KR20190064510A (en) * | 2017-11-30 | 2019-06-10 | 솔브레인 주식회사 | Compound and organic light emitting device comprising the same |
| CN110678449A (en) * | 2017-06-16 | 2020-01-10 | 材料科学有限公司 | Organic compound and organic electroluminescent element comprising same |
| KR20200067500A (en) * | 2018-12-04 | 2020-06-12 | 솔브레인 주식회사 | Heterocyclic compound and organic light emitting device comprising the same |
| CN111683940A (en) * | 2018-05-29 | 2020-09-18 | 株式会社Lg化学 | Heterocyclic compound and organic light emitting device including the same |
| CN112119514A (en) * | 2018-07-24 | 2020-12-22 | 株式会社Lg化学 | Organic light emitting device |
| CN112159361A (en) * | 2020-11-06 | 2021-01-01 | 烟台显华化工科技有限公司 | Electron transport material, organic electroluminescent device and display device |
| CN112321521A (en) * | 2020-11-06 | 2021-02-05 | 烟台显华化工科技有限公司 | Electron transport material, organic electroluminescent device and display device |
| CN112534593A (en) * | 2018-12-07 | 2021-03-19 | 株式会社Lg化学 | Organic light emitting diode |
-
2021
- 2021-05-07 CN CN202110496937.2A patent/CN113234010A/en active Pending
Patent Citations (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20100001274A (en) * | 2008-06-26 | 2010-01-06 | 제일모직주식회사 | Organic compound, and organic photoelectric device including the same |
| KR20110049554A (en) * | 2009-11-05 | 2011-05-12 | 엘지디스플레이 주식회사 | Blue color fluorescence compounds and organic light emitting diode comprising thereof |
| WO2011086863A1 (en) * | 2010-01-15 | 2011-07-21 | 富士フイルム株式会社 | Organic electroluminescent element |
| KR20120116434A (en) * | 2010-01-15 | 2012-10-22 | 후지필름 가부시키가이샤 | Organic electroluminescent element |
| WO2011102586A1 (en) * | 2010-02-22 | 2011-08-25 | 제일모직 주식회사 | Compound for an organic photoelectric device and photoelectric device including same |
| US20140367656A1 (en) * | 2013-06-12 | 2014-12-18 | Samsung Display Co., Ltd. | Organic light-emitting diode |
| CN106164215A (en) * | 2014-04-04 | 2016-11-23 | 株式会社Lg化学 | Organic luminescent device |
| KR20150122343A (en) * | 2014-04-23 | 2015-11-02 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| KR20150131998A (en) * | 2014-05-15 | 2015-11-25 | 주식회사 엘지화학 | Hetero-cyclic compound and organic light emitting device comprising the same |
| KR20150140241A (en) * | 2014-06-05 | 2015-12-15 | 주식회사 엘지화학 | Hetero-cyclic compound and organic light emitting device comprising the same |
| KR20160005944A (en) * | 2014-07-08 | 2016-01-18 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| CN107531651A (en) * | 2015-06-01 | 2018-01-02 | 株式会社Lg化学 | Heterocyclic compound and the organic luminescent device for including it |
| KR20160149527A (en) * | 2015-06-18 | 2016-12-28 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
| KR20180061074A (en) * | 2016-11-29 | 2018-06-07 | 주식회사 엘지화학 | Novel hetero-cyclic compound and organic light emitting device comprising the same |
| CN110678449A (en) * | 2017-06-16 | 2020-01-10 | 材料科学有限公司 | Organic compound and organic electroluminescent element comprising same |
| CN109575001A (en) * | 2017-09-29 | 2019-04-05 | Cmdl有限公司 | 3- dibenzofurans based triazine derivative organic compound and the organic electroluminescence device comprising it |
| KR20190064510A (en) * | 2017-11-30 | 2019-06-10 | 솔브레인 주식회사 | Compound and organic light emitting device comprising the same |
| CN111683940A (en) * | 2018-05-29 | 2020-09-18 | 株式会社Lg化学 | Heterocyclic compound and organic light emitting device including the same |
| CN112119514A (en) * | 2018-07-24 | 2020-12-22 | 株式会社Lg化学 | Organic light emitting device |
| KR20200067500A (en) * | 2018-12-04 | 2020-06-12 | 솔브레인 주식회사 | Heterocyclic compound and organic light emitting device comprising the same |
| CN112534593A (en) * | 2018-12-07 | 2021-03-19 | 株式会社Lg化学 | Organic light emitting diode |
| CN109705148A (en) * | 2018-12-28 | 2019-05-03 | 武汉天马微电子有限公司 | Aromatic cycle compound, display panel and display device |
| CN112159361A (en) * | 2020-11-06 | 2021-01-01 | 烟台显华化工科技有限公司 | Electron transport material, organic electroluminescent device and display device |
| CN112321521A (en) * | 2020-11-06 | 2021-02-05 | 烟台显华化工科技有限公司 | Electron transport material, organic electroluminescent device and display device |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111635415B (en) | Compound, electron transport material and organic electroluminescent device | |
| CN111548353A (en) | Organic light-emitting material and organic electroluminescent device | |
| CN113264911A (en) | Compound, organic light-emitting material and organic electroluminescent device | |
| CN113816898A (en) | Compound, electron transport material, organic electroluminescent device and display device | |
| CN112321521B (en) | Electron transport material, organic electroluminescent device and display device | |
| CN110818675A (en) | Organic compound and application thereof | |
| CN113264871A (en) | Compound, electron transport material and organic electroluminescent device | |
| CN111548354A (en) | Organic light-emitting material and organic electroluminescent device | |
| CN112125873A (en) | Compound, hole transport material, organic electroluminescent device and display device | |
| CN112125892B (en) | Compound, electron transport material and organic electroluminescent device | |
| CN112174918B (en) | Compound, hole transport material, organic electroluminescent device and display device | |
| CN112125813A (en) | Compound, hole transport material and organic electroluminescent device | |
| CN113321649B (en) | Compound, electron transport material and organic electroluminescent device | |
| CN112341470B (en) | Electron transport material, organic electroluminescent device and display device | |
| CN115991699A (en) | Naphthalene bridging double-suction fragment compound | |
| CN112110885B (en) | Hole transport material, organic electroluminescent device and display device | |
| CN112028879B (en) | Electron transport material, organic electroluminescent device and display device | |
| CN113045553A (en) | Aza-aromatic compound used as electron transport material and application thereof | |
| CN113024512A (en) | Aromatic heterocyclic compound used as electron transport material and application thereof | |
| CN113307764B (en) | Compound, electron transport material, organic electroluminescent device and display device | |
| CN113321641B (en) | Compound, electron transport material, organic electroluminescent device and display device | |
| CN113234010A (en) | Compound, electron transport material, organic electroluminescent device and display device | |
| CN112125861B (en) | Compound, electron transport material and organic electroluminescent device | |
| CN112341447B (en) | Electron transport material, organic electroluminescent device and display device | |
| CN112341438B (en) | Electron transport material, organic electroluminescent device and display device |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20210810 |
|
| RJ01 | Rejection of invention patent application after publication |