CN112778300B - Organic compound and organic electroluminescent device containing the same - Google Patents
Organic compound and organic electroluminescent device containing the same Download PDFInfo
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- CN112778300B CN112778300B CN201911073852.2A CN201911073852A CN112778300B CN 112778300 B CN112778300 B CN 112778300B CN 201911073852 A CN201911073852 A CN 201911073852A CN 112778300 B CN112778300 B CN 112778300B
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 15
- 125000003118 aryl group Chemical group 0.000 claims abstract description 17
- 125000001424 substituent group Chemical group 0.000 claims abstract description 10
- 239000000463 material Substances 0.000 claims description 48
- 239000012044 organic layer Substances 0.000 claims description 5
- 239000010409 thin film Substances 0.000 claims description 5
- 125000005264 aryl amine group Chemical group 0.000 claims description 3
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 230000005669 field effect Effects 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 13
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 abstract description 5
- 125000000732 arylene group Chemical group 0.000 abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 5
- 229910052736 halogen Inorganic materials 0.000 abstract description 5
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 4
- 150000002367 halogens Chemical class 0.000 abstract description 4
- 125000005549 heteroarylene group Chemical group 0.000 abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 4
- 125000000304 alkynyl group Chemical group 0.000 abstract description 3
- 150000004982 aromatic amines Chemical class 0.000 abstract description 3
- 125000005309 thioalkoxy group Chemical group 0.000 abstract description 3
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 abstract description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 2
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 101
- 239000010410 layer Substances 0.000 description 94
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
- -1 cyano-substituted imidazole structure Chemical group 0.000 description 63
- 238000006243 chemical reaction Methods 0.000 description 41
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 38
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- 238000002347 injection Methods 0.000 description 28
- 239000007924 injection Substances 0.000 description 28
- 229910052757 nitrogen Inorganic materials 0.000 description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
- 238000002360 preparation method Methods 0.000 description 21
- 238000001704 evaporation Methods 0.000 description 20
- 238000004440 column chromatography Methods 0.000 description 19
- 230000015572 biosynthetic process Effects 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 230000008020 evaporation Effects 0.000 description 15
- 238000002390 rotary evaporation Methods 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 14
- 230000005525 hole transport 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
- 238000010992 reflux Methods 0.000 description 14
- 230000002950 deficient Effects 0.000 description 13
- 238000005516 engineering process Methods 0.000 description 13
- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- 230000005012 migration Effects 0.000 description 8
- 238000013508 migration Methods 0.000 description 8
- 239000011368 organic material Substances 0.000 description 8
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- NSGDYZCDUPSTQT-UHFFFAOYSA-N N-[5-bromo-1-[(4-fluorophenyl)methyl]-4-methyl-2-oxopyridin-3-yl]cycloheptanecarboxamide Chemical compound Cc1c(Br)cn(Cc2ccc(F)cc2)c(=O)c1NC(=O)C1CCCCCC1 NSGDYZCDUPSTQT-UHFFFAOYSA-N 0.000 description 7
- 230000005540 biological transmission Effects 0.000 description 7
- 230000000903 blocking effect Effects 0.000 description 7
- 239000010408 film Substances 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical class C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 239000012043 crude product Substances 0.000 description 6
- 239000002019 doping agent Substances 0.000 description 6
- 238000005401 electroluminescence Methods 0.000 description 6
- 125000002883 imidazolyl group Chemical group 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 239000002356 single layer Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000006555 catalytic reaction Methods 0.000 description 5
- 230000021615 conjugation Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 230000005611 electricity Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 229910052697 platinum Inorganic materials 0.000 description 5
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 5
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 4
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 4
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 4
- 235000011056 potassium acetate Nutrition 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- VNFWTIYUKDMAOP-UHFFFAOYSA-N sphos Chemical compound COC1=CC=CC(OC)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 VNFWTIYUKDMAOP-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 3
- HBQUOLGAXBYZGR-UHFFFAOYSA-N 2,4,6-triphenyl-1,3,5-triazine Chemical compound C1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 HBQUOLGAXBYZGR-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000010549 co-Evaporation Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000005286 illumination Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- XRNVSPDQTPVECU-UHFFFAOYSA-N (4-bromophenyl)methanamine Chemical compound NCC1=CC=C(Br)C=C1 XRNVSPDQTPVECU-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 229910052805 deuterium Inorganic materials 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
- 239000002346 layers by function Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 2
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- BJFPYGGTDAYECS-UHFFFAOYSA-N (3-chlorophenyl)methanamine Chemical compound NCC1=CC=CC(Cl)=C1 BJFPYGGTDAYECS-UHFFFAOYSA-N 0.000 description 1
- UZDPQDBLCJDUAX-UHFFFAOYSA-N (4-chloro-3-methylphenyl)boronic acid Chemical compound CC1=CC(B(O)O)=CC=C1Cl UZDPQDBLCJDUAX-UHFFFAOYSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 1
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 description 1
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 1
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 1
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 1
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 description 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 description 1
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 description 1
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 description 1
- FNKCOUREFBNNHG-UHFFFAOYSA-N 1,3-dibromo-5-chlorobenzene Chemical compound ClC1=CC(Br)=CC(Br)=C1 FNKCOUREFBNNHG-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- GIMXBORKCIXLDB-UHFFFAOYSA-N 1h-imidazo[4,5-b]quinoline Chemical group C1=CC=C2NC3=NC=NC3=CC2=C1 GIMXBORKCIXLDB-UHFFFAOYSA-N 0.000 description 1
- HNZUKQQNZRMNGS-UHFFFAOYSA-N 2-(3-bromophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound BrC1=CC=CC(C=2N=C(N=C(N=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HNZUKQQNZRMNGS-UHFFFAOYSA-N 0.000 description 1
- AYHGAQGOMUQMTR-UHFFFAOYSA-N 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine Chemical compound C1=CC(Br)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 AYHGAQGOMUQMTR-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- BHVHKOVPWZKVCC-UHFFFAOYSA-N 4-(4-bromophenyl)benzonitrile Chemical compound C1=CC(Br)=CC=C1C1=CC=C(C#N)C=C1 BHVHKOVPWZKVCC-UHFFFAOYSA-N 0.000 description 1
- HQAIROMRVBVWSK-UHFFFAOYSA-N 4-chloro-2-methylquinoline Chemical compound C1=CC=CC2=NC(C)=CC(Cl)=C21 HQAIROMRVBVWSK-UHFFFAOYSA-N 0.000 description 1
- SQRYQSKJZVQJAY-UHFFFAOYSA-N 6-bromo-2-methylquinoline Chemical compound C1=C(Br)C=CC2=NC(C)=CC=C21 SQRYQSKJZVQJAY-UHFFFAOYSA-N 0.000 description 1
- BGEVROQFKHXUQA-UHFFFAOYSA-N 71012-25-4 Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=C1C1=CC=CC=C1N2 BGEVROQFKHXUQA-UHFFFAOYSA-N 0.000 description 1
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- JTPHKHUWLNQSSU-UHFFFAOYSA-N C1=CC=CC=2C=CC=3C=4C=CC=CC4NC3C21.C2(=CC=CC1=CC=CC=C21)N2C1=CC=CC=C1C=1C=CC=CC21 Chemical compound C1=CC=CC=2C=CC=3C=4C=CC=CC4NC3C21.C2(=CC=CC1=CC=CC=C21)N2C1=CC=CC=C1C=1C=CC=CC21 JTPHKHUWLNQSSU-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- 101000930898 Cryphonectria parasitica Glyceraldehyde-3-phosphate dehydrogenase Proteins 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 101000766357 Ruditapes philippinarum Big defensin Proteins 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 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
- 230000003321 amplification Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- LPTWEDZIPSKWDG-UHFFFAOYSA-N benzenesulfonic acid;dodecane Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCCCCCCCCCCC LPTWEDZIPSKWDG-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 239000011162 core material Substances 0.000 description 1
- 229940076286 cupric acetate Drugs 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 239000012969 di-tertiary-butyl peroxide Substances 0.000 description 1
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
- 229960005544 indolocarbazole Drugs 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000005990 isobenzothienyl group Chemical group 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- JCDAUYWOHOLVMH-UHFFFAOYSA-N phenanthren-9-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC3=CC=CC=C3C2=C1 JCDAUYWOHOLVMH-UHFFFAOYSA-N 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 125000005592 polycycloalkyl group Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- 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
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C09K2211/1018—Heterocyclic compounds
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- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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- Electroluminescent Light Sources (AREA)
Abstract
An organic compound having a structure as shown in (1):wherein L is 1 And L 2 Each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene, or a substituted or unsubstituted C3-C30 heteroarylene; ar (Ar) 1 And Ar is a group 2 Each independently selected from a substituted or unsubstituted C6 to C30 aryl or a substituted or unsubstituted C3 to C30 heteroaryl; r is halogen, C1-C30 alkyl, C3-C30 cycloalkyl, C1-C30 alkoxy, amino, C6-C30 arylamine or nitro; p and n are integers of 0 to 6, p+n is not more than 6, and when p is 0, L 1 Is not a single bond; when each of the above-mentioned substituted or unsubstituted groups has a substituent, the substituent is selected from one or more of halogen, C1-C30 alkyl, C3-C30 cycloalkyl, C2-C30 alkenyl, C2-C30 alkynyl, cyano, nitro, C1-C30 alkoxy, C1-C30 thioalkoxy, C6-C30 aryl and C3-C60 heteroaryl. The application also relates to an organic electroluminescent device using the organic compound.
Description
Technical Field
The invention relates to a novel organic compound, in particular to an organic compound and application thereof in an organic electroluminescent device.
Background
An organic electroluminescent (OLED: organic Light Emission Diodes) device is a device with a sandwich-like structure, comprising positive and negative electrode layers and an organic functional material layer sandwiched between the electrode layers. And applying voltage to the electrode of the OLED device, injecting positive charges from the positive electrode, injecting negative charges from the negative electrode, and transferring and meeting the positive charges and the negative charges in the organic layer to emit light compositely under the action of an electric field. Because the OLED device has the advantages of high brightness, quick response, wide viewing angle, simple process, flexibility and the like, the OLED device has a great deal of attention in the novel display technical field and the novel illumination technical field. At present, the technology is widely applied to display panels of products such as novel illumination lamps, smart phones and tablet computers, and further expands the application field of large-size display products such as televisions, and is a novel display technology with rapid development and high technical requirements.
With the continuous advancement of the OLED in the two fields of illumination and display, the research on the core materials of the OLED is also more focused. This is because an efficient, long-life OLED device is typically the result of an optimized match of device structures and various organic materials, which provides great opportunities and challenges for chemists to design and develop functionalized materials of various structures. Common functionalized organic materials are: a hole injecting material, a hole transporting material, a hole blocking material, an electron injecting material, an electron transporting material, an electron blocking material, a light emitting host material, a light emitting guest (dye), and the like.
In order to prepare the OLED light-emitting device with lower driving voltage, better light-emitting efficiency and longer service life of the device, the performance of the OLED device is continuously improved, the structure and the manufacturing process of the OLED device are required to be innovated, and the photoelectric functional material in the OLED device is required to be continuously researched and innovated so as to prepare the functional material with higher performance. Based on this, the OLED materials community has been striving to develop new organic electroluminescent materials to achieve low driving voltages, high luminous efficiency and better lifetime of the device.
In the current manufacturers of OLED panels, commonly used electron transport materials include single oxazoles, thiazoles, imidazoles, triazoles, or triazines.
Disclosure of Invention
Problems to be solved by the invention
However, in order to further meet the demand for the continuous improvement of the photoelectric performance of OLED devices, and the demand for energy saving of mobile electronic devices, there is a continuous need to develop new and efficient OLED materials, wherein the development of new electron transport materials with high electron injection capability and high mobility has great significance.
Solution to the problem
In order to solve the problems in the prior art, the inventor intensively researches to find that the conjugated group is introduced at a specific position of the quinolino cyano-substituted imidazole structure, so that molecules have good plane conjugation, and the electron mobility, especially the electron-deficient conjugated group, is improved, and the electron injection and migration performance are improved, so that the compound with excellent performance, which can be used for an organic electronic device, is obtained.
Specifically, the present invention provides an organic compound characterized by having a structure as shown in (1):
wherein L is 1 And L 2 Each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene, or a substituted or unsubstituted C3-C30 heteroarylene; ar (Ar) 1 And Ar is a group 2 Each independently selected from a substituted or unsubstituted C6 to C30 aryl or a substituted or unsubstituted C3 to C30 heteroaryl; r is halogen, C1-C30 alkyl, C3-C30 cycloalkyl, C1-C30 alkoxy, amino, C6-C30 arylamine or nitro; p and n are integers of 0 to 6, p+n is not more than 6, and when p is 0, L 1 Is not a single bond; when each of the above-mentioned substituted or unsubstituted groups has a substituent, the substituent is selected from one or more of halogen, C1-C30 alkyl, C3-C30 cycloalkyl, C2-C30 alkenyl, C2-C30 alkynyl, cyano, nitro, C1-C30 alkoxy, C1-C30 thioalkoxy, C6-C30 aryl and C3-C60 heteroaryl.
The specific reason why the compound of the present invention is excellent in the performance as an electron transport layer material in an organic electroluminescent device is not clear, and it is presumed that the following reasons are possible: the parent nucleus of the compound with the general formula is of a quinolino cyano-substituted imidazole structure, has good electron-deficient property, is favorable for electron injection, and is connected with an aryl or heteroaryl conjugated structure at a specific position of the parent nucleus to enlarge a conjugated system of the parent nucleus, so that molecules have good plane conjugation, and especially the parent nucleus is combined with electron-deficient conjugated groups such as triazine, quinazoline, cyano and the like at the specific position, so that the compound has stronger electron-deficient type, and is favorable for electron injection. Therefore, under the synergistic effect of the above-mentioned various features, when the compound of the general formula of the present invention is used as an electron transport layer material of an organic electroluminescent device, the electron injection and migration efficiency in the device can be effectively improved, thereby ensuring that the device obtains excellent effects of high luminous efficiency and low driving voltage.
In addition, the inventors have found that, in the compounds of the above general formula, when an aryl or heteroaryl group is not attached to the quinoline ring of the parent nucleus (i.e., p=0, and thus the aryl or heteroaryl group must be directly or indirectly attached to the imidazole ring), if the aryl or heteroaryl group is directly attached to the imidazole ring (i.e., L 1 A single bond), the light emitting efficiency, the driving voltage, and the like of the organic electroluminescent device using the corresponding compound as an electron transport layer material are insufficient as compared with the case where an aryl group or a heteroaryl group is connected to an imidazole ring via an arylene group or a heteroarylene group and an aryl group or a heteroaryl group is connected to a quinoline ring. The reason for this is not clear, and may be that conjugation is insufficient due to steric hindrance at the time of direct connection. In addition, the synthesis of the above-mentioned compounds in which the aryl or heteroaryl group is directly attached to the imidazole ring is difficult, which may also be caused by steric hindrance.
In the present invention, the "electron-deficient substituent" means a group having a reduced electron cloud density on a benzene ring after the hydrogen on the benzene ring is substituted with the group, and generally such a group has a Hammett value of more than 0.6. The Hammett value refers to the characterization of the charge affinity for a particular group, and is a measure of the electron withdrawing group (positive Hammett value) or the electron donating group (negative Hammett value). Hammett's equation is described in more detail in Thomas H.Lowry and KatheleenSchueller Richardson, "Mechanism and Theory In Organic Chemistry', new York,1987, pages 143-151, which is incorporated herein by reference. Such groups may be exemplified by, but are not limited to: triazinyl, pyrimidinyl, benzopyrimidinyl, benzopyridyl, naphthyridinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, pyridazinyl, and alkyl or aryl substituted radicals as described above.
In the present specification, the expression of Ca to Cb means that the group has a carbon number of a to b, and unless otherwise specified, the carbon number generally excludes the carbon number of a substituent. In the present invention, the expression of chemical elements includes the concept of isotopes of the same chemical nature, for example, the expression of "hydrogen", and also includes the concept of "deuterium", "tritium" of the same chemical nature.
In the present specification, the expression "-" of a ring structure indicates that the linking site is located at any position on the ring structure capable of bonding.
In the present specification, the C6-C30 aryl group is a group selected from the group consisting of phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthryl, benzophenanthryl, pyrenyl, hole, perylene, fluoranthryl, naphthacene, pentacene, benzopyrene, biphenyl, terphenyl, tetrabiphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, trimeric indenyl, heterotrimeric indenyl, spirotrimeric indenyl, spiroheterotrimeric indenyl. Specifically, the biphenyl group is selected from the group consisting of 2-biphenyl group, 3-biphenyl group and 4-biphenyl group; terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl comprises 1-naphthyl or 2-naphthyl; the anthracenyl is selected from the group consisting of 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; and the tetracenyl is selected from the group consisting of 1-tetracenyl, 2-tetracenyl and 9-tetracenyl. C6-C30 arylene is similar to C6-C30 aryl, except that the above groups are changed to the corresponding subunits.
Heteroatoms in the present invention generally refer to atoms or groups of atoms selected from N, O, S, P, si and Se, preferably selected from N, O, S.
In the present specification, examples of the C3 to C30 heteroaryl group include: nitrogen-containing heteroaryl, oxygen-containing heteroaryl, sulfur-containing heteroaryl, and the like, and specific examples thereof include: furyl, thienyl, pyrrolyl, pyridyl, benzofuryl, benzothienyl, isobenzofuryl, isobenzothienyl, indolyl, isoindolyl, dibenzofuryl, dibenzothienyl, carbazolyl, derivatives thereof, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolinyl, benzo-6, 7-quinolinyl, benzo-7, 8-quinolinyl, phenothiazinyl, phenazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthyridinyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, thienyl, benzoxazolyl, naphthyridinyl, anthracenooxazolyl, phenanthroizolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthracenyl, 2,7, 2,3, 6, 4-dipyrene, 1, 4-dipyrene, 4, 5-dipyrene, 10-tetraazaperylene, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarboline, phenanthroline, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazole, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazole, and the like, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole benzocarbazole, dibenzocarbazole, or indolocarbazole. C3-C30 heteroarylene is similar to C3-C30 heteroaryl, except that the above groups are changed to the corresponding subunits.
In the present specification, examples of the C1-C30 alkyl group include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, adamantyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2-trifluoroethyl and the like. C1-C30 alkoxy, C1-C30 thioalkoxy are similar to C1-C30 alkyl except that one-O-, -S-is correspondingly added to each group.
In the present specification, the C3-C30 cycloalkyl group includes a monocycloalkyl group and a polycycloalkyl group, and for example, may be cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or the like.
In the present specification, examples of the C6 to C30 arylamine group include: diphenylamino, dimethylanilino, isopropyldiphenylamino, dinaphthylanilino, naphthylanilino, and the like.
In the present specification, examples of the C2 to C30 alkenyl groups include: ethenyl, propenyl, 1-butenyl, and the like; examples of the C2-C30 alkynyl group include: ethynyl, propynyl, 1-butynyl, and the like.
In the present specification, examples of halogen include: fluorine, chlorine, bromine, iodine, etc., preferably fluorine.
The compound of the above general formula (1) of the present invention specifically has structures shown in (1-1) to (1-7):
the above-mentioned compound of the formula (1) of the present invention is preferably Ar 1 And Ar is a group 2 Each independently selected from the substituted or unsubstituted structures:
the expression "dotted line" in the above structure indicates that the linking site may be located at any position on the ring structure where a bond can be formed.
The above-mentioned compound of the formula (1) of the present invention is preferably Ar 1 And/or Ar 2 The electron-deficient group can increase electron affinity of molecules and regulate dipole moment of the molecules, thereby being beneficial to improving electron injection and migration capability.
The above-mentioned compounds of the formula (1) according to the invention are preferably L 1 And L 2 Each is independently selected from single bond, phenylene or biphenylene, which can lead the plane to have a certain twist angle, thereby avoiding the effect that the molecules are excessively stacked to cause quenching easily and influencing the efficiency of the device.
The compound of the general formula (1) is preferably n is 0, so that the prepared device has good performance, and meanwhile, the molecular structure is simple and the synthesis is convenient.
The above-mentioned compounds of the general formula (1) of the present invention are preferably selected from the structures shown by the following C1 to C94, but these compounds are merely representative:
the compound has higher electron affinity, thus having stronger electron withdrawing capability, being suitable for being used as an electron transmission material, being not limited to organic electroluminescent materials, and being applicable to the technical fields of optical sensors, solar batteries, lighting elements, organic thin film transistors, organic field effect transistors, organic thin film solar batteries, information labels, electronic artificial skin sheets, sheet scanners and the like, large-area sensors, electronic papers and the like.
The invention also provides an organic electroluminescent device, which comprises a first electrode, a second electrode and at least one organic layer positioned between the first electrode and the second electrode, and is characterized in that the organic layer contains the organic compound.
Specifically, the invention provides an organic electroluminescent device, which comprises a substrate, and an anode layer, a plurality of luminous functional layers and a cathode layer which are sequentially formed on the substrate; the light-emitting functional layer comprises a hole injection layer, a hole transmission layer, a light-emitting layer and an electron transmission layer, wherein the hole injection layer is formed on the anode layer, the hole transmission layer is formed on the hole injection layer, the cathode layer is formed on the electron transmission layer, and the light-emitting layer is arranged between the hole transmission layer and the electron transmission layer; wherein the electron transport layer contains the compound of the general formula of the present invention represented by the above formula (1).
Effects of the invention
The compound of the general formula adopts the combination of the quinolino cyano-substituted imidazole and the electron-deficient groups such as triazine, quinazoline, cyano and the like, and compared with the structures such as single oxazole, thiazole, imidazole, triazole or triazine and the like commonly used in the prior art, the structure of the compound of the general formula has relatively stronger electron-deficient property, so that the injection of electrons is facilitated. Meanwhile, the electron-deficient group with a large conjugated structure in the compound of the invention ensures that the molecule has good plane conjugation, thereby being beneficial to improving the mobility of electrons. The structural characteristics of the two aspects can lead the molecule as a whole to show good electron injection and migration performances. Therefore, when the compound of the present invention is used as an electron transport layer material in an organic electroluminescent device, electron injection and migration efficiency in the device can be effectively improved, thereby ensuring excellent effects of high luminous efficiency and low driving voltage of the device.
In addition, the preparation process of the compound is simple and easy to implement, raw materials are easy to obtain, and the compound is suitable for mass production and amplification.
Detailed Description
The technical solution of the present invention will be further described by the following specific embodiments, and it should be apparent to those skilled in the art that the examples are only for aiding in understanding the present invention and should not be construed as limiting the present invention in any way.
The various chemicals used in the following synthesis examples, such as ethyl acetate, sodium sulfate, toluene, tetrahydrofuran, methylene chloride, acetic acid, potassium carbonate, and other basic chemical raw materials were purchased from Shanghai Taitan technologies and chemical Co., ltd. The mass spectrometer used for determining the following compounds was ZAB-HS type mass spectrometer measurement (manufactured by Micromass Co., UK).
Synthesis of intermediate M:
the 2-methylquinoline derivative M-1 (0.1 mol,1 eq), arylbenzylamine M-2 (0.3 mol,3 eq), TMSCN (0.3 mol,3 eq), NH 4 I(0.02mol，0.2eq)，Ph 2 PO 2 H (0.1 mol,1 eq) and NH 4 BF 4 (0.1 mol,1 eq) was charged into a DMA (1L) -containing three-necked flask equipped with a platinum electrode. Under the catalysis of electricity (J=10mA/cm) 2 ) The reaction is carried out for 15 to 24 hours by heating to 90 ℃ in an oil bath, and TLC monitors the completion of the reaction. The reaction solution was cooled to room temperature, and the solvent was removed by rotary evaporation under reduced pressure. 1.5L of water was added and extracted with ethyl acetate (1L. Times.3). And combining ethyl acetate phases, drying by anhydrous sodium sulfate, carrying out suction filtration, removing ethyl acetate by rotary evaporation, and purifying the obtained crude product by column chromatography to obtain an intermediate M.
Synthesis example 1: synthesis of Compound C2
(1) Preparation of Compound 1-1
2-methylquinoline (14.3 g,0.1mol,1 eq), 4-bromobenzylamine (55.5 g,0.3mol,3 eq), TMSCN (30 g,0.3mol,3 eq), NH 4 I(2.9g，0.02mol，0.2eq)，Ph 2 PO 2 H (21.8 g,0.1mol,1 eq) and NH 4 BF 4 (10.5 g,0.1mol,1 eq) was charged into a DMA (1L) -containing three-necked flask equipped with a platinum electrodeIs a kind of medium. Under the catalysis of electricity (J=10mA/cm) 2 ) The reaction was heated to 90℃in an oil bath for 20 hours and monitored by TLC. The reaction solution was cooled to room temperature, and the solvent was removed by rotary evaporation under reduced pressure. 1.5L of water was added and extracted with ethyl acetate (1L. Times.3). The ethyl acetate phases were combined, dried over anhydrous sodium sulfate, suction filtered, and ethyl acetate was removed by rotary evaporation, and the obtained crude product was purified by column chromatography to give intermediate 1-1 (27.2 g, yield 80%).
(2) Preparation of Compound C2
Compound 1-1 (6.2 g,18 mmol), compound 2- (4-boronic acid pinacol) phenyl-4, 6-diphenyl-1, 3,5 triazine (7.8 g,18 mmol), potassium carbonate (7.45 g,54 mmol), pd (PPh 3 ) 4 (208 mg,0.18 mmol) was added to a flask containing 100mL toluene and 25mL ethanol and 25mL water, the nitrogen was replaced and the reaction was heated at reflux under nitrogen for 5 hours, and TLC showed completion of the reaction. The precipitated solid was filtered, rinsed with water and ethanol, and dried, and then purified by column chromatography to give compound C2 (8.9 g, yield 86%). Calculated molecular weight: 576.21, found C/Z:576.2.
synthesis example 2: synthesis of Compound C22
(1) Preparation of Compound 2-1
2-methylquinoline (14.3 g,0.1mol,1 eq), 3-chlorobenzylamine (42.3 g,0.3mol,3 eq), TMSCN (30 g,0.3mol,3 eq), NH 4 I(2.9g，0.02mol，0.2eq)，Ph 2 PO 2 H (21.8 g,0.1mol,1 eq) and NH 4 BF 4 (10.5 g,0.1mol,1 eq) was charged into a three-necked flask equipped with a platinum electrode containing DMA (1L). Under the catalysis of electricity (J=10mA/cm) 2 ) The reaction was heated to 90℃in an oil bath for 22 hours and monitored by TLC. The reaction solution was cooled to room temperature, and the solvent was removed by rotary evaporation under reduced pressure. 1.5L of water was added and extracted with ethyl acetate (1L. Times.3). The ethyl acetate phases were combined, dried over anhydrous sodium sulfate, suction filtered, and ethyl acetate was removed by rotary evaporation, and the obtained crude product was purified by column chromatography to give intermediate 2-1 (18.2 g, yield 60%).
(2) Preparation of Compound 2-2
Compound 2-1 (15.5 g,50 mmol), pinacol diboronate (19 g,75 mmol) and potassium acetate (14.7 g,150 mmol) were added to a flask containing 1, 4-dioxane (300 mL), and palladium acetate (224 mg,1 mmol), SPhos (820 mg,2 mmol) were added after displacing nitrogen with stirring at room temperature. After the addition was completed, the reaction was stirred at reflux for 4 hours and TLC monitored for the end of the reaction. The 1, 4-dioxane was removed by rotary evaporation, water and methylene chloride were added to the mixture, the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and purified by column chromatography to give compound 2-2 (16.7 g, yield 85%).
(3) Preparation of Compound C22
Compound 2-2 (7.1 g,18 mmol), compound 2- (3-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine (7.0 g,18 mmol), potassium carbonate (7.45 g,54 mmol), pd (PPh) 3 ) 4 (208 mg,0.18 mmol) was added to a flask containing 100mL toluene and 25mL ethanol and 25mL water, the nitrogen was replaced and the reaction was heated at reflux under nitrogen for 7 hours, and TLC showed completion of the reaction. The precipitated solid was filtered, rinsed with water and ethanol, and dried, and then purified by column chromatography to give compound C22 (8.5 g, yield 82%). Calculated molecular weight: 576.21, found C/Z:576.2.
synthesis example 3: synthesis of Compound C41
(1) Preparation of Compound 3-1
The compound 4- (4-bromophenyl) benzonitrile (25.7 g,0.1 mol), 3-methyl-4-chloro-phenylboronic acid (107 g,0.4 mol), potassium carbonate (17 g,0.1 mol), pd (PPh) 3 ) 4 (1155 mg,1 mmol) was added to a flask containing toluene/ethanol/water 400mL/100mL/100mL, nitrogen was replaced and the reaction was heated at reflux under nitrogen for 4 hours, and TLC showed completion of the reaction. Cooling to room temperature, separating, extracting the aqueous phase with ethyl acetate, mixing the organic phases, drying over anhydrous sodium sulfate, and separating and purifying by column chromatography to obtain compound 3-1 (25 g, 83%).
(2) Preparation of Compound 3-2
Compound 3-1 (15.2 g,50 mmol), pinacol diboronate (19 g,75 mmol) and potassium acetate (14.7 g,150 mmol) were added to a flask containing 1, 4-dioxane (300 mL), and palladium acetate (224 mg,1 mmol), SPhos (820 mg,2 mmol) were added after displacing nitrogen with stirring at room temperature. After the addition was completed, the reaction was stirred at reflux for 8 hours and TLC monitored for the end of the reaction. The 1, 4-dioxane was removed by rotary evaporation, water and methylene chloride were added to the mixture, the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and purified by column chromatography to give compound 3-2 (17 g, yield 86%).
(3) Preparation of Compound C41
Compound 1-1 (6.2 g,18 mmol), compound 3-2 (7.1 g,18 mmol), potassium carbonate (7.45 g,54 mmol), pd (PPh) 3 ) 4 (208 mg,0.18 mmol) was added to a flask containing 100mL toluene and 25mL ethanol and 25mL water, the nitrogen was replaced and the reaction was heated at reflux under nitrogen for 6 hours, and TLC showed completion of the reaction. The precipitated solid was filtered, rinsed with water and ethanol, and dried, and then purified by column chromatography to give compound C41 (8.4 g, yield 87%). Calculated molecular weight: 536.20, found C/Z:536.2.
synthesis example 4: synthesis of Compound C51
(1) Preparation of Compound 4-1
2-methyl-6-bromoquinoline (22.1 g,0.1mol,1 eq), benzylamine (32.1 g,0.3mol,3 eq), TMSCN (30 g,0.3mol,3 eq), NH 4 I(2.9g，0.02mol，0.2eq)，Ph 2 PO 2 H (21.8 g,0.1mol,1 eq) and NH 4 BF 4 (10.5 g,0.1mol,1 eq) was charged into a three-necked flask equipped with a platinum electrode containing DMA (1L). Under the catalysis of electricity (J=10mA/cm) 2 ) The reaction was heated to 90℃in an oil bath for 18 hours and monitored by TLC. The reaction solution was cooled to room temperature, and the solvent was removed by rotary evaporation under reduced pressure. 1.5L of water was added and extracted with ethyl acetate (1L. Times.3). The ethyl acetate phases were combined, dried over anhydrous sodium sulfate, suction filtered and the ethyl acetate was removed by rotary evaporation, and the obtained crude product was purified by column chromatography to give intermediate 4-1 (31.2 g, yield 90%)。
(2) Preparation of Compound C51
Compound 4-1 (6.2 g,18 mmol), compound 2- (4-boronic acid pinacol) phenyl-4, 6-diphenyl-1, 3,5 triazine (7.8 g,18 mmol), potassium carbonate (7.45 g,54 mmol), pd (PPh 3 ) 4 (208 mg,0.18 mmol) was added to a flask containing 100mL toluene and 25mL ethanol and 25mL water, the nitrogen was replaced and the reaction was heated at reflux under nitrogen for 7 hours, and TLC showed completion of the reaction. The precipitated solid was filtered, rinsed with water and ethanol, and dried, and then purified by column chromatography to give compound C51 (8.6 g, yield 83%). Calculated molecular weight: 576.21, found C/Z:576.2.
synthesis example 5: synthesis of Compound C71
(1) Preparation of Compound 5-1
2-methyl-4-chloro-quinoline (17.7 g,0.1mol,1 eq), benzylamine (32.1 g,0.3mol,3 eq), TMSCN (30 g,0.3mol,3 eq), NH 4 I(2.9g，0.02mol，0.2eq)，Ph 2 PO 2 H (21.8 g,0.1mol,1 eq) and NH 4 BF 4 (10.5 g,0.1mol,1 eq) was charged into a three-necked flask equipped with a platinum electrode containing DMA (1L). Under the catalysis of electricity (J=10mA/cm) 2 ) The reaction was heated to 90℃in an oil bath for 21 hours, and TLC was monitored for completion. The reaction solution was cooled to room temperature, and the solvent was removed by rotary evaporation under reduced pressure. 1.5L of water was added and extracted with ethyl acetate (1L. Times.3). The ethyl acetate phases were combined, dried over anhydrous sodium sulfate, suction filtered, and ethyl acetate was removed by rotary evaporation, and the obtained crude product was purified by column chromatography to give intermediate 5-1 (21.2 g, yield 70%).
(2) Preparation of Compound 5-2
Compound 5-1 (15.2 g,50 mmol), pinacol diboronate (19 g,75 mmol) and potassium acetate (14.7 g,150 mmol) were added to a flask containing 1, 4-dioxane (300 mL), and palladium acetate (224 mg,1 mmol), SPhos (820 mg,2 mmol) was added after displacing nitrogen with stirring at room temperature. After the addition was completed, the reaction was stirred at reflux for 10 hours and TLC monitored for the end of the reaction. The 1, 4-dioxane was removed by rotary evaporation, water and methylene chloride were added to the mixture, the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and purified by column chromatography to give compound 5-2 (15.8 g, yield 80%).
(3) Preparation of Compound C71
Compound 5-2 (7.1 g,18 mmol), compound 2- (4-bromophenyl) -4, 6-diphenyl-1, 3, 5-triazine (7 g,18 mmol), potassium carbonate (7.45 g,54 mmol), pd (PPh) 3 ) 4 (208 mg,0.18 mmol) was added to a flask containing 100mL toluene and 25mL ethanol and 25mL water, the nitrogen was replaced and the reaction was heated at reflux under nitrogen for 4 hours, and TLC showed completion of the reaction. The precipitated solid was filtered, rinsed with water and ethanol, and dried, and then purified by column chromatography to give compound C71 (7.9 g, yield 77%). Calculated molecular weight: 576.21, found C/Z:576.2.
synthesis example 6: synthesis of Compound C46
(1) Preparation of Compound 6-1
The compound 3, 5-dibromochlorobenzene (40 g,0.15 mol), 9-phenanthreneboronic acid (22.2 g,0.1 mol), potassium carbonate (41.4 g,0.3 mol), pd (PPh) 3 ) 4 (1155 mg,1 mmol) was added to a flask containing toluene/ethanol/water 400mL/100mL/100mL, nitrogen was replaced and the reaction was heated at reflux under nitrogen for 3 hours, and TLC showed completion of the reaction. Cooling to room temperature, separating, extracting the aqueous phase with ethyl acetate, mixing the organic phases, drying over anhydrous sodium sulfate, and separating and purifying by column chromatography to obtain compound 6-1 (18.3 g, 50%).
(2) Preparation of Compound 6-2
Compound 6-1 (18.3 g,0.05 mol), phenylboronic acid (6.1 g,0.05 mol), potassium carbonate (20.7 g,0.15 mol), pd (PPh) 3 ) 4 (578 mg,0.5 mmol) was added to a flask containing toluene/ethanol/water 200mL/50mL/50mL, nitrogen was replaced and the reaction was heated at reflux under nitrogen for 2 hours, and TLC showed completion. Cooling to room temperature, separating, extracting the aqueous phase with ethyl acetate, mixing the organic phases, drying over anhydrous sodium sulfate, and collecting column layerThe compound 6-2 (16.9 g, 93%) was obtained by separation and purification.
(3) Preparation of Compound 6-3
Compound 6-2 (14.5 g,40 mmol), pinacol diboronate (15.2 g,60 mmol) and potassium acetate (11.7 g,120 mmol) were added to a flask containing 1, 4-dioxane (200 mL), and palladium acetate (224 mg,1 mmol), SPhos (820 mg,2 mmol) was added after displacing nitrogen with stirring at room temperature. After the addition was completed, the reaction was stirred at reflux for 12 hours and TLC monitored for the end of the reaction. The 1, 4-dioxane was removed by rotary evaporation, water and methylene chloride were added to the mixture, the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and purified by column chromatography to give compound 6-3 (15.5 g, yield 85%).
(4) Preparation of Compound C46
Compound 6-3 (8.2 g,18 mmol), compound 1-1 (4.5 g,18 mmol), potassium carbonate (7.45 g,54 mmol), pd (PPh) 3 ) 4 (208 mg,0.18 mmol) was added to a flask containing 100mL toluene and 25mL ethanol and 25mL water, the nitrogen was replaced and the reaction was heated at reflux under nitrogen for 5 hours, and TLC showed completion of the reaction. The precipitated solid was filtered, rinsed with water and ethanol, and dried, and then purified by column chromatography to give compound C46 (9.1 g, yield 85%). Calculated molecular weight: 597.22, found C/Z:597.2.
synthesis of comparative example 1: synthesis of compound ET-Y
(1) Preparation of Compound ET-Y1
Cuprous iodide (19 g,0.1mol,1 eq), water and cupric acetate (20 g,0.1mol,1 eq) were dissolved in DMSO (750 ml), and then 4-bromobenzylamine (55.5 g,0.3mol,3 eq), 2-methylquinoline (14.3 g,0.1mol,1 eq), di-tert-butyl peroxide DTBP (29.2 g,0.2mol,2 eq) was added to the reaction system. The reaction was heated to 110℃for 24 hours in an oil bath and monitored by TLC for completion. The reaction solution was cooled to room temperature, 1.5L of water was added and extracted with ethyl acetate (1 l×3). The ethyl acetate phases were combined, dried over anhydrous sodium sulfate, suction filtered, and ethyl acetate was removed by rotary evaporation, and the resulting crude product was purified by column chromatography to give intermediate ET-Y1 (27.2 g, yield 80%).
(2) Preparation of Compound ET-Y
The compound ET-Y1 (5.8 g,18 mmol), the compound 2- (4-boronic acid pinacol) phenyl-4, 6-diphenyl-1, 3,5 triazine (7.8 g,18 mmol), potassium carbonate (7.45 g,54 mmol), pd (PPh 3 ) 4 (208 mg,0.18 mmol) was added to a flask containing 100mL toluene and 25mL ethanol and 25mL water, the nitrogen was replaced and the reaction was heated at reflux under nitrogen for 6 hours, and TLC showed completion of the reaction. The precipitated solid was filtered, rinsed with water and ethanol, and dried, and then purified by column chromatography to give the compound ET-Y (8.2 g, yield 83%). Calculated molecular weight: 551.21, found C/Z:551.2.
device embodiment
The invention also provides an organic electroluminescent device containing the compound of the embodiment. An embodiment of an OLED is described below as an organic electroluminescent device. The OLED of this embodiment includes a first electrode and a second electrode, and an organic material layer between the electrodes. The organic material may in turn be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
In particular embodiments, a substrate may be used below the first electrode or above the second electrode. The substrates are all glass or polymer materials with excellent mechanical strength, thermal stability, water resistance and transparency. A Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode may be formed by sputtering or depositing a material serving as the first electrode on the substrate. When the first electrode is used as the anode, indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO) 2 ) An oxide transparent conductive material such as zinc oxide (ZnO), and any combination thereof. When the first electrode is used as the cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag) and any combination thereof can be used.
The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compounds used as the organic material layer may be small organic molecules, large organic molecules and polymers, and combinations thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer hole transport layer containing only one compound and a single layer hole transport layer containing a plurality of compounds. The hole transport region may have a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL).
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or conductive dopant containing polymers such as polystyrene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives such as the compounds shown below HT-1 to HT-34; or any combination thereof.
The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more of the compounds HT-1 through HT-34 described above, or one or more of the compounds HI1 through HI3 described below; one or more of the compounds HT-1 to HT-34 may also be used to dope one or more of the compounds HI1 to HI3 described below.
The light emitting layer includes a light emitting dye (i.e., dopant) that can emit different wavelength spectrums, and may also include a Host material (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The plurality of monochromatic light emitting layers with different colors can be arranged in a plane according to the pixel pattern, or can be stacked together to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light emitting layer may be a single color light emitting layer capable of simultaneously emitting different colors such as red, green, and blue.
According to different technologies, the luminescent layer material can be made of different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescence luminescent material and the like. In an OLED device, a single light emitting technology may be used, or a combination of different light emitting technologies may be used. The different luminescent materials classified by the technology can emit light of the same color, and can also emit light of different colors.
In one aspect of the invention, the light-emitting layer employs fluorescence electroluminescence technology. The luminescent layer fluorescent host material thereof may be selected from, but is not limited to, one or more combinations of BFH-1 through BFH-16 listed below.
In one aspect of the invention, the light-emitting layer employs fluorescence electroluminescence technology. The luminescent layer fluorescent dopant thereof may be selected from, but is not limited to, one or more combinations of BFD-1 through BFD-12 listed below.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The luminescent layer host material is selected from, but not limited to, one or more of GPH-1 to GPH-80.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The luminescent layer phosphorescent dopant thereof may be selected from, but is not limited to, one or more combinations of GPD-1 to GPD-47 listed below.
Wherein D is deuterium.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The luminescent layer phosphorescent dopant thereof may be selected from, but is not limited to, one or more combinations of the RPD-1 through RPD-28 listed below.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The luminescent layer phosphorescent dopant thereof may be selected from, but is not limited to, one or more combinations of YPD-1 through YPD-11 listed below.
The organic EL light emitting device of the present invention further includes an electron transport region between the light emitting layer and the cathode. The electron transport region may be an Electron Transport Layer (ETL) of a single layer structure including a single layer electron transport layer containing only one compound and a single layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
The electron transport region may also be formed by applying the compound of the present invention to a multi-layer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL), although the material of the electron transport region may also be combined with one or more of ET-1 to ET-57 listed below.
The device may further include an electron injection layer between the electron transport layer and the cathode, the electron injection layer material including, but not limited to, a combination of one or more of the following: liQ, liF, naCl, csF, li 2 O、Cs 2 CO 3 BaO, na, li and/or Ca.
The technical effects and advantages of the present invention are demonstrated and verified by testing practical use properties in the organic electroluminescent device by applying the compounds of the present invention specifically to the organic electroluminescent device.
Example 1
The embodiment provides a preparation method of an organic electroluminescent device, which specifically comprises the following steps:
the glass plate coated with the ITO transparent conductive layer was sonicated in commercial cleaners, rinsed in deionized water, and rinsed in acetone: ultrasonic degreasing in ethanol mixed solvent, baking in clean environment to completely remove water, cleaning with ultraviolet light and ozone, and bombarding surface with low-energy cation beam;
placing the glass substrate with anode in vacuum chamber, vacuumizing to pressure less than 10 -5 Pa, vacuum evaporating HI-3 as a hole injection layer on the anode layer film by using a multi-source co-evaporation method, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10nm;
vacuum evaporation HT-4 is carried out on the hole injection layer to serve as a first hole transport layer of the device, the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 40nm;
vacuum evaporating HT-14 on the first hole transport layer to obtain a second hole transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of the evaporation is 10nm;
vacuum evaporating a luminescent layer of the device on the second hole transport layer, wherein the luminescent layer comprises a main material and a dye material, the evaporation rate of the main material BFH-4 is regulated to be 0.1nm/s by utilizing a multi-source co-evaporation method, the evaporation rate of the dye BFD-4 is set to be 5% in proportion, and the total film thickness of evaporation is 20nm;
vacuum evaporating ET-17 on the luminescent layer as a hole blocking layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 5nm;
evaporating an electron transport layer on the hole blocking layer by utilizing a multi-source co-evaporation method, wherein the evaporation rate of the compound C2 is regulated to be 0.1nm/s, the ratio of the evaporation rate to the ET-57 evaporation rate is set to be 100%, and the total evaporation film thickness is 23nm;
LiF with the thickness of 1nm is vacuum evaporated on an Electron Transport Layer (ETL) to serve as an electron injection layer, and an Al layer with the thickness of 80nm serves as a cathode of the device.
Examples 2 to 6
Examples 2-6 were prepared in the same manner as in example 1, except that the electron transport layer compound C2 was replaced with the compound shown in Table 1, respectively.
Comparative example 1
Comparative example 1 was prepared in the same manner as in example 1 except that the electron transport layer compound C2 was replaced with the existing compound ET-X having the chemical formula:
comparative example 2
Comparative example 2 was prepared in the same manner as in example 1 except that the electron transport layer compound C2 was replaced with the compound ET-Y obtained in synthetic comparative example 1, and the chemical formula was:
the organic electroluminescent device prepared by the above procedure was subjected to the following performance measurement:
the driving voltage and current efficiency of the organic electroluminescent devices prepared in examples 1 to 6 and comparative examples 1 to 2 were measured using a Photo Research company PR 750 type optical radiometer, an ST-86LA type luminance meter (university of Beijing photoelectric instrumentation Co.) and a Keithley4200 test system at the same luminance. Specifically, the luminance of the organic electroluminescent device was measured to reach 1000cd/m by increasing the voltage at a rate of 0.1V per second 2 The voltage at the time is the driving voltage, and the current density at the time is measured; the ratio of brightness to current density is the current efficiency; the results of the performance test are shown in Table 1.
Table 1:
as can be seen from Table 1, in the case that other materials are the same in the structure of the organic electroluminescent device, the organic electroluminescent devices provided in embodiments 1 to 6 of the present invention have higher current efficiency and lower driving voltage, wherein the current efficiency is 8.02 to 8.65cd/A and the driving voltage is 4.07 to 4.25V.
The compound ET-X of comparative example 1 contains quinolinocyano substituted imidazole group, the driving voltage of the device is 5.96V, the current efficiency is 4.93cd/A, and the performance is greatly different from that of the device of the example. The reason for the speculation may be: the electron transport materials of examples 1 to 6 are much larger in the electron affinity and planar conjugation degree as a whole than that of comparative example 1 on the basis of the structure in which the quinolino cyano-substituted imidazole mother nucleus is solely substituted with phenyl group, and the quinoline ring of the mother nucleus or the phenyl group is additionally linked with aryl or heteroaryl substituent, thus resulting in much higher electron injection and transport ability than that of the compound ET-X of comparative example 1. In addition, the compound ET-X of comparative example 1 has too small a molecular weight and a relatively low Tg, which is detrimental to the thermal stability of the material.
Compound ET-Y of comparative example 2 contains a quinolinoimidazole group, the driving voltage of the device was 4.63V, the current efficiency was 7.11cd/A, and both the current efficiency and the driving voltage were inferior to those of the device of example. The reason for the speculation may be: compared with comparative example 2, the electron transport materials of examples 1-6 have stronger electron affinities than the mother nucleus of quinoline-cyano-substituted imidazole without cyano-substituted quinoline-imidazole, and have more suitable molecular dipole moments with new molecules composed of other electron-deficient groups, so that the electron transport materials have stronger electron injection and migration capabilities.
In addition, the inventors have found that although the organic electroluminescent device of example 6 has lower driving voltage and higher current efficiency than those of comparative examples 1 to 2, the above parameters are slightly inferior to those of examples 1 to 5. The reason for this is presumed to be: in the compounds of examples 1-5 of the present invention, the quinolino cyano-substituted imidazole is used as a large conjugated electron-deficient group, and the quinolino cyano-substituted imidazole is further connected to an electron-deficient group such as triazine, pyrimidine or cyano-substituted phenyl through an arylene group, and the electron-deficient groups increase the electron affinity of the whole molecule, so that electron injection is facilitated, and the dipole moment of the whole molecule is adjusted, so that the compound has appropriate electron injection and migration capability. The new electron transport material thus constructed has higher electron injection and migration properties, thus enabling the device to have higher current efficiency and lower driving voltage.
The experimental data show that the novel organic material provided by the invention is used as an electron transport material of an organic electroluminescent device, is an organic luminescent functional material with good performance, and has a wide application prospect.
It is apparent that the above examples are given by way of illustration only and are not limiting of the embodiments. Other variations or modifications of the above teachings will be apparent to those of ordinary skill in the art. It is not necessary here nor is it exhaustive of all embodiments. While still being apparent from variations or modifications that may be made by those skilled in the art are within the scope of the invention.
Claims (8)
1. An organic compound having a structure as shown in (1-7):
wherein L is 1 Selected from phenylene or biphenylene;
r is C6-C30 arylamine group;
n＝0；
Ar 1 selected from the substituted or unsubstituted structures:
wherein Ar is 1 When each of the above-mentioned substituted or unsubstituted groups has a substituent, the substituent is selected from the group consisting of C6-C30 aryl groups.
2. An organic compound having a structure represented by (1-1) to (1-6):
wherein L is 1 Is a single bond;
r is C 6 ～C 30 Arylamine groups, n=0;
Ar 1 and Ar is a group 2 Each independently selected from the substituted or unsubstituted structures:
L 2 is phenylene or biphenylene;
wherein Ar is 1 Or Ar 2 When each of the above-mentioned substituted or unsubstituted groups has a substituent, the substituent is selected from the group consisting of C6-C30 aryl groups.
3. An organic compound characterized by having one of the structures shown below:
4. an organic compound having one of the structures shown in C41 to C45:
5. use of an organic compound according to any one of claims 1 to 4 in an organic electronic device.
6. The use according to claim 5 in organic electroluminescent devices, optical sensors, solar cells, lighting elements, organic thin film transistors, organic field effect transistors, organic thin film solar cells, information labels, electronic artificial skin sheets, sheet scanners or electronic papers.
7. Use of the organic compound according to any one of claims 1 to 4 as an electron transport material in an organic electroluminescent device.
8. An organic electroluminescent device comprising a first electrode, a second electrode, and at least one organic layer between the first electrode and the second electrode, wherein the organic layer contains the organic compound according to any one of claims 1 to 4.
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| KR20150137266A (en) * | 2014-05-29 | 2015-12-09 | (주)피엔에이치테크 | An electroluminescent compound and an electroluminescent device comprising the same |
| TW201918542A (en) * | 2017-09-27 | 2019-05-16 | 南韓商東進世美肯股份有限公司 | Novel compound and organic electroluminescent device including the same capable of ensuring high efficiency, prolonged service life, low driving voltage and driving stability of the organic electroluminescent device |
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| KR20150137266A (en) * | 2014-05-29 | 2015-12-09 | (주)피엔에이치테크 | An electroluminescent compound and an electroluminescent device comprising the same |
| TW201918542A (en) * | 2017-09-27 | 2019-05-16 | 南韓商東進世美肯股份有限公司 | Novel compound and organic electroluminescent device including the same capable of ensuring high efficiency, prolonged service life, low driving voltage and driving stability of the organic electroluminescent device |
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