CN111333671A - Luminescent material, application thereof and organic electroluminescent device comprising luminescent material - Google Patents
Luminescent material, application thereof and organic electroluminescent device comprising luminescent material Download PDFInfo
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- CN111333671A CN111333671A CN202010181899.7A CN202010181899A CN111333671A CN 111333671 A CN111333671 A CN 111333671A CN 202010181899 A CN202010181899 A CN 202010181899A CN 111333671 A CN111333671 A CN 111333671A
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- 239000000463 material Substances 0.000 title claims abstract description 53
- -1 nitro, cyano, amino Chemical group 0.000 claims abstract description 93
- 150000001875 compounds Chemical class 0.000 claims abstract description 86
- 125000003118 aryl group Chemical group 0.000 claims abstract description 43
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 43
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 31
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 29
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 27
- 150000002367 halogens Chemical class 0.000 claims abstract description 27
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 26
- 125000001769 aryl amino group Chemical group 0.000 claims abstract description 25
- 125000005241 heteroarylamino group Chemical group 0.000 claims abstract description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
- 239000001257 hydrogen Substances 0.000 claims abstract description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 22
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 20
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 19
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 19
- 125000005309 thioalkoxy group Chemical group 0.000 claims abstract description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 13
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims abstract description 12
- 229910052805 deuterium Inorganic materials 0.000 claims abstract description 12
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 10
- 239000010410 layer Substances 0.000 claims description 94
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
- 230000005525 hole transport Effects 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000001725 pyrenyl group Chemical group 0.000 claims description 8
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 7
- 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 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 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
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 claims description 6
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 6
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 5
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 5
- 125000005990 isobenzothienyl group Chemical group 0.000 claims description 5
- 239000002346 layers by function Substances 0.000 claims description 5
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 2
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims description 2
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims description 2
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 claims description 2
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 2
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 2
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims description 2
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 claims description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 2
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims description 2
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 claims description 2
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 2
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 claims description 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 2
- CPDDXQJCPYHULE-UHFFFAOYSA-N 4,5,14,16-tetrazapentacyclo[9.7.1.12,6.015,19.010,20]icosa-1(18),2,4,6,8,10(20),11(19),12,14,16-decaene Chemical group C1=CC(C2=CC=CC=3C2=C2C=NN=3)=C3C2=CC=NC3=N1 CPDDXQJCPYHULE-UHFFFAOYSA-N 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 125000004802 cyanophenyl group Chemical group 0.000 claims description 2
- 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 claims description 2
- 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 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
- 125000001207 fluorophenyl group Chemical group 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 2
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 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 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 2
- 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 claims description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 2
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 2
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 2
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 2
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 229910052727 yttrium Inorganic materials 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 1
- 125000005561 phenanthryl group Chemical group 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 28
- 238000003786 synthesis reaction Methods 0.000 description 28
- 239000000126 substance Substances 0.000 description 25
- 238000000921 elemental analysis Methods 0.000 description 21
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 21
- 239000000975 dye Substances 0.000 description 20
- 239000007787 solid Substances 0.000 description 20
- 150000001793 charged compounds Chemical class 0.000 description 19
- 238000004128 high performance liquid chromatography Methods 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 14
- 238000002347 injection Methods 0.000 description 13
- 239000007924 injection Substances 0.000 description 13
- 238000001704 evaporation Methods 0.000 description 12
- 238000000034 method Methods 0.000 description 10
- 230000008020 evaporation Effects 0.000 description 9
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
- 230000000903 blocking effect Effects 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
- 238000012986 modification Methods 0.000 description 6
- 230000004048 modification Effects 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- 239000002356 single layer Substances 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 4
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 4
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 239000008204 material by function Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
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- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 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
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 239000003341 Bronsted base Substances 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 238000010268 HPLC based assay Methods 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- OEMGCAOEZNBNAE-UHFFFAOYSA-N [P].[Li] Chemical compound [P].[Li] OEMGCAOEZNBNAE-UHFFFAOYSA-N 0.000 description 1
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- 230000003321 amplification Effects 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000004888 barrier function Effects 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
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- PPTSBERGOGHCHC-UHFFFAOYSA-N boron lithium Chemical compound [Li].[B] PPTSBERGOGHCHC-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- MPVDXIMFBOLMNW-UHFFFAOYSA-N chembl1615565 Chemical compound OC1=CC=C2C=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=C1N=NC1=CC=CC=C1 MPVDXIMFBOLMNW-UHFFFAOYSA-N 0.000 description 1
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- 238000010549 co-Evaporation Methods 0.000 description 1
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- 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
- 239000011162 core material Substances 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
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 239000012761 high-performance material Substances 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 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
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000006263 metalation reaction Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000002093 peripheral effect Effects 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
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 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
- 238000003756 stirring Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- BKDLGMUIXWPYGD-UHFFFAOYSA-N tert-butyllithium Chemical compound [Li]C(C)(C)C BKDLGMUIXWPYGD-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 238000012546 transfer Methods 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
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Abstract
The invention relates to a novel compound, application thereof and an organic electroluminescent device containing the compound, wherein the compound has a structure shown in the following formula:
the ring A is selected from one of a monocyclic nitrogen heteroaromatic ring of substituted or unsubstituted C5-C60 and a condensed nitrogen heteroaromatic ring of substituted or unsubstituted C5-C60; x1And X2Are each independently selected from NR, R1～R8Each independently selected from hydrogen, deuterium orSubstituted or unsubstituted one of the following groups: halogen, chain alkyl of C1-C30, cycloalkyl of C3-C30, alkoxy of C1-C10, thioalkoxy of C1-C10, carbonyl, carboxyl, nitro, cyano, amino, arylamino of C6-C30, heteroarylamino of C3-C30, monocyclic aryl of C6-C60, condensed ring aryl of C6-C60, aryloxy of C6-C60, monocyclic heteroaryl of C5-C60 or condensed ring heteroaryl of C5-C60. The compound of the present invention shows excellent device performance and stability when used as a light emitting material in an OLED device. The invention also protects the organic electroluminescent device adopting the compound with the general formula.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a novel organic compound, application thereof and an organic electroluminescent device containing the compound.
Background
Organic Light Emission Diodes (OLED) are a kind of devices with sandwich-like structure, which includes positive and negative electrode films and Organic functional material layers sandwiched between the electrode films. And applying voltage to the electrodes of the OLED device, injecting positive charges from the positive electrode and injecting negative charges from the negative electrode, and transferring the positive charges and the negative charges in the organic layer under the action of an electric field to meet for composite luminescence. Because the OLED device has the advantages of high brightness, fast response, wide viewing angle, simple process, flexibility and the like, the OLED device is concerned in the field of novel display technology and novel illumination technology. At present, the technology is widely applied to display panels of products such as novel lighting 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 fast development and high technical requirements.
With the continuous advance of OLEDs in both lighting and display areas, much attention has been paid to the research on their core materials. This is because an efficient, long-lived OLED device is generally the result of an optimized configuration of the device structure and various organic materials, which provides great opportunities and challenges for chemists to design and develop functional materials with various structures. Common functionalized organic materials are: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, and light emitting host materials and light emitting objects (dyes), and the like.
In order to prepare an OLED light-emitting device with lower driving voltage, better light-emitting efficiency and longer service life, the performance of the OLED device is continuously improved, the structure and the manufacturing process of the OLED device need to be innovated, and photoelectric functional materials in the OLED device need to be continuously researched and innovated, so that functional materials with higher performance can be prepared. Based on this, the OLED material industry has been working on developing new organic electroluminescent materials to achieve low starting voltage, high luminous efficiency and better lifetime of the device.
The MR-TADF material has the advantages of high color purity and high luminous efficiency, and has attracted extensive attention in the scientific research and industrial fields. However, the peripheral substituent has little influence on the S1 energy level, that is, the luminescent color of the material is difficult to control, and the light color is always limited in the blue-deep blue region, which greatly limits the further application of the MR-TADF material in the fields of high-resolution display, full-color display, white light illumination, and the like.
Disclosure of Invention
In order to solve the above technical problems, the present invention provides a novel organic compound, wherein the specific general formula of the compound of the present invention is shown as the following formula (1):
in formula (1): ring A represents a ring simultaneously with the groups B and X, respectively1From B and X2A group formed by fusing and connecting six-membered ring structures, wherein the ring A is selected from one of a substituted or unsubstituted monocyclic nitrogen heteroaromatic ring of C5-C60 and a substituted or unsubstituted fused nitrogen heteroaromatic ring of C5-C60; preferably, ring A represents one of a substituted or unsubstituted monocyclic nitrogen heteroaromatic ring of C13-C60, a substituted or unsubstituted fused nitrogen heteroaromatic ring of C13-C60;
said X1And X2Each independently selected from NR, wherein R may be bonded to an adjacent benzene ring by-O-, -S-, -C (-R') 2-, or a single bond, and each independently selected from one of the following substituted or unsubstituted groups: chain alkyl of C1-C30, cycloalkyl of C3-C30, haloalkyl of C1-C30, alkoxy of C1-C30, alkenyl of C2-C30, alkynyl of C3-C30, monocyclic aryl of C6-C60, fused ring aryl of C6-C60, aryloxy of C6-C60, monocyclic heteroaryl of C5-C60 or fused ring heteroaryl of C5-C60;
the R is1～R8Are respectively and independentlySelected from hydrogen, deuterium or one of the following substituted or unsubstituted groups: halogen, chain alkyl of C1-C30, cycloalkyl of C3-C30, alkoxy of C1-C10, thioalkoxy of C1-C10, carbonyl, carboxyl, nitro, cyano, amino, arylamino of C6-C30, heteroarylamino of C3-C30, monocyclic aryl of C6-C60, condensed ring aryl of C6-C60, aryloxy of C6-C60, monocyclic heteroaryl of C5-C60 or condensed ring heteroaryl of C5-C60, and R is R1～R20Wherein two adjacent groups can be bonded with each other to form one of a five-membered or six-membered aryl ring of C5-C30, a five-membered or six-membered heteroaryl ring of C5-C30, and at least one hydrogen in the formed ring can be substituted by any one of arylamino of C6-C30, heteroarylamino of C3-C30, monocyclic aryl of C6-C60, fused ring aryl of C6-C60, aryloxy of C6-C60, monocyclic heteroaryl of C5-C60, fused ring heteroaryl of C5-C60, halogen, chain alkyl of C1-C30, cycloalkyl of C3-C30, alkoxy of C1-C10, thioalkoxy of C1-C10, carbonyl, carboxyl, nitro, cyano, and amino;
when the above groups have substituents, the substituents are respectively and independently one selected from deuterium, halogen, cyano, chain alkyl of C1-C30, cycloalkyl of C3-C30, alkoxy of C1-C10, arylamino of C6-C30, heteroarylamino of C3-C30, aryl of C6-C30 and heteroaryl of C3-C30.
Further, the ring A in formula (1) has a structure as shown in formula A1 or A2:
in the formula A1, Y1～Y3Each independently selected from N or CR1, and Y1～Y3At least one of which is N; the R1 is selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, substituted or unsubstituted C1-C10 silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C1 aryl aminoOne of unsubstituted C3-C30 heteroaryl amino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl; two adjacent R1 can be fused to form a ring;
in formula A1, ring D is represented by the formulae B and Y1And Y2A group formed by fusing and connecting six-membered ring structures, wherein the ring D is selected from one of substituted or unsubstituted C6-C60 monocyclic aryl, substituted or unsubstituted C6-C60 fused ring aryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C5-C60 monocyclic heteroaryl and substituted or unsubstituted C5-C60 fused ring heteroaryl;
preferably, the ring D is selected from any one of a substituted or unsubstituted halogen, a chain alkyl group having C1 to C30, a cycloalkyl group having C3 to C30, an alkoxy group having C1 to C10, a thioalkoxy group having C1 to C10, a carbonyl group, a carboxyl group, a nitro group, a cyano group, and an amino group:
in the formula A2, Z1～Z7Each independently selected from N or CR2, and Z1～Z7At least one of which is N; the R2 is selected from one of hydrogen substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, substituted or unsubstituted C1-C10 silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl; two adjacent R2 s may be fused together to form a ring.
Still further, in formula A1, Y is1Or Y2At least one of them is N, said Y3Selected from N or CR 1;
or in formula A1, Y1Is N, said Y2、Y3Each is independently selected from N or CR 1;
or in formula A1, Y2The content of the N is N,said Y is1、Y3Each is independently selected from N or CR 1;
or in formula A1, Y1Is N, said Y2、Y3Are all selected from CR 1;
or in formula A1, Y2Is N, said Y1、Y3Are all selected from CR 1.
Still further, in formula A2, Z1～Z7At least two of which are N;
or in formula A2, Z1、Z2、Z6And Z7At least one of which is N, said Z3～Z5Each is independently selected from N or CR 2;
or in formula A2, Z1、Z2、Z6And Z7At least two of which are N, said Z3～Z5Each is independently selected from N or CR 2;
or in formula A2, Z1And Z7Is N, said Z2～Z6Are all selected from CR 2;
or in formula A2, Z2And Z7Is N, said Z1、Z3～Z6Are all selected from CR 2;
or in formula A2, Z2And Z6Is N, said Z1、Z3～Z5、Z7Are all selected from CR 2.
Or in formula A2, Z2Is N, said Z1、Z3～Z7Are all selected from CR 2.
The compound represented by the above general formula (1) of the present invention is more preferably a compound having a structure represented by any one of the following structural formulae (2) to (6):
in formulae (2) to (6), the X1And X2Are all as defined in formula (1);
the R is1、R2、R3、R4、R5、R5、R7、R8、R9、R10、R12、R13And R14Each independently selected from hydrogen, deuterium, or one of the following substituted or unsubstituted groups: halogen, chain alkyl of C1-C30, cycloalkyl of C3-C30, alkoxy of C1-C10, thioalkoxy of C1-C10, carbonyl, carboxyl, nitro, cyano, amino, arylamino of C6-C30, heteroarylamino of C3-C30, monocyclic aryl of C6-C60, condensed ring aryl of C6-C60, aryloxy of C6-C60, monocyclic heteroaryl of C5-C60 or condensed ring heteroaryl of C5-C60, and R is R1～R14Wherein adjacent two groups may be bonded to each other to form one of a five-or six-membered aryl ring of C5-C30, a five-or six-membered heteroaryl ring of C5-C30 together with the adjacent benzene ring, and at least one hydrogen in the formed ring may be substituted by any one of an arylamino group of C6-C30, a heteroarylamino group of C3-C30, a monocyclic aryl group of C6-C60, a condensed ring aryl group of C6-C60, an aryloxy group of C6-C60, a monocyclic heteroaryl group of C5-C60, a condensed ring heteroaryl group of C5-C60, a halogen, a chain alkyl group of C1-C30, a cycloalkyl group of C3-C30, an alkoxy group of C1-C10, a thioalkoxy group of C1-C10, a carbonyl group, a carboxyl group, a nitro group, a cyano group, and an amino group.
Still further preferably, in the formula (2):
the R is12And R13Or said R is10And R11One of five-or six-membered aryl rings of C5 to C30, five-or six-membered heteroaryl rings of C5 to C30, bonded to each other and taken together with the adjacent benzene ring, and at least one hydrogen in the formed rings may be substituted by any one of arylamino of C6 to C30, heteroarylamino of C3 to C30, monocyclic aryl of C6 to C60, fused-ring aryl of C6 to C60, aryloxy of C6 to C60, monocyclic heteroaryl of C5 to C60, fused-ring heteroaryl of C5 to C60, halogen, chain alkyl of C1 to C30, cycloalkyl of C3 to C30, alkoxy of C1 to C10, thioalkoxy of C1 to C10, carbonyl, carboxyl, nitro, cyano, or amino; more preferably, said R is12And R13Or said R is10And R11Bonded to each other and forming, together with the adjacent benzene ring, any of the following substituted or unsubstituted groups: naphthyl, anthracenyl, benzanthracenyl, phenanthrenyl, benzophenanthrenyl, pyrenyl, fluoranthenyl, tetracenyl, pentacenyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl.
Still further preferably, in the formula (3):
the R is12And R13Or said R is10And R11One of five-or six-membered aryl rings of C5 to C30, five-or six-membered heteroaryl rings of C5 to C30, bonded to each other and taken together with the adjacent benzene ring, and at least one hydrogen in the formed rings may be substituted by any one of arylamino of C6 to C30, heteroarylamino of C3 to C30, monocyclic aryl of C6 to C60, fused-ring aryl of C6 to C60, aryloxy of C6 to C60, monocyclic heteroaryl of C5 to C60, fused-ring heteroaryl of C5 to C60, halogen, chain alkyl of C1 to C30, cycloalkyl of C3 to C30, alkoxy of C1 to C10, thioalkoxy of C1 to C10, carbonyl, carboxyl, nitro, cyano, or amino; more preferably, said R is12And R13Or said R is10And R11Bonded to each other and forming, together with the adjacent benzene ring, any of the following substituted or unsubstituted groups: naphthyl, anthracenyl, benzanthracenyl, phenanthrenyl, benzophenanthrenyl, pyrenyl, fluoranthenyl, tetracenyl, pentacenyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl.
Still more preferably, in the above formulae (2) to (6):
said R1～R14Each independently selected from hydrogen, deuterium, or one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexylCyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2, 2-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzanthryl, phenanthrenyl, benzophenanthrenyl, pyrenyl, fluorenyl, perylenyl, anthryl, fluoranthenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, couplet phenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, triindenyl, isotridecyl, spirocycloisoindolyl, furanyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, thienyl, benzothienyl, isobenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazyl, pyridyl, pentaflurophenyl, benzopyranyl, anthryl, pyrenyl, benzopyrenyl, terphenyl, etc, Quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalimidazolyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthraoxazolyl, phenanthrolyoxazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyrazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazenanthranyl, 2, 7-diazapyryl, 2, 3-diazapyryl, 1, 6-diazapyryl, 1, 8-diazapyryl, 4, 5-diazapyryl, 4,5,9, 10-tetraazaperylenes, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbazinyl, phenanthrolinyl, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazolyl, 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, benzothiadiazolyl, 9-dimethylazinyl, triarylamino, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrole, piperidine, methoxy, silyl, orA combination selected from the above two substituent groups;
and R is1～R14Wherein two adjacent groups can be bonded with each other to form one of a five-membered or six-membered aryl ring of C5-C30, a five-membered or six-membered heteroaryl ring of C5-C30, and at least one hydrogen in the formed ring can be substituted by any one of arylamino of C6-C30, heteroarylamino of C3-C30, monocyclic aryl of C6-C60, fused ring aryl of C6-C60, aryloxy of C6-C60, monocyclic heteroaryl of C5-C60, fused ring heteroaryl of C5-C60, halogen, chain alkyl of C1-C30, cycloalkyl of C3-C30, alkoxy of C1-C10, thioalkoxy of C1-C10, carbonyl, carboxyl, nitro, cyano, and amino;
when the above groups have substituents, the substituents are respectively and independently one selected from deuterium, halogen, cyano, chain alkyl of C1-C30, cycloalkyl of C3-C30, alkoxy of C1-C10, arylamino of C6-C30, heteroarylamino of C3-C30, aryl of C6-C30 and heteroaryl of C3-C30.
Further, the compound represented by the general formula (1) of the present invention may preferably be a compound having the following specific structure: C1-C284, these compounds being representative only:
the present invention also provides an organic electroluminescent device comprising a substrate comprising a first electrode, a second electrode and one or more organic layers interposed between the first electrode and the second electrode, wherein the organic layers comprise a compound represented by any one of the above general formulae (1) to (6).
Specifically, embodiments of the present invention provide an organic electroluminescent device including a substrate, and an anode layer, a plurality of organic functional layers, and a cathode layer sequentially formed on the substrate; the organic functional layer comprises a hole injection layer, a hole transport layer, a light emitting layer and an electron transport layer, wherein the hole injection layer is formed on the anode layer, the hole transport layer is formed on the hole injection layer, the cathode layer is formed on the electron transport layer, and the light emitting layer is arranged between the hole transport layer and the electron transport layer; among them, the light-emitting layer preferably contains the compound of the general formula of the present invention represented by any one of the above formulae (1) to (6).
The OLED device prepared by the compound has low starting voltage, high luminous efficiency and better service life, and can meet the requirements of current panel manufacturing enterprises on high-performance materials.
As another aspect of the present invention, there is also provided a use of the compound as described above as a functional material in an organic electronic device including an organic electroluminescent device, an optical sensor, a solar cell, a lighting element, an organic thin film transistor, an organic field effect transistor, an organic thin film solar cell, an information tag, an electronic artificial skin sheet, a sheet-type scanner, or electronic paper. Preferably, the compounds according to the invention are used in organic electroluminescent devices, in particular, preferably as a primer material in organic electroluminescent devices.
The specific reason why the above-mentioned compound of the present invention is excellent as an electron transport layer material in an organic electroluminescent device is not clear, and the following reason is presumed:
in the general formula compound structure, nitrogen heterocyclic aromatic rings with electron-withdrawing property are introduced at the A ring position, so that the conjugated skeleton of molecules can be increased, and the charge transfer state of the molecules is enhanced within a certain range (HOMO and LUMO are locally separated), thereby maximally red-shifting the spectrum of the MR-TADF material on the premise of keeping B/N multiple resonance, and realizing the emission of green light, yellow light and even red light.
In addition, the preparation process of the compound is simple and feasible, the raw materials are easy to obtain, and the compound is suitable for mass production and amplification.
Drawings
FIG. 1: the structure of the organic electroluminescent device prepared by the invention is shown in the figure, wherein 1 is a substrate, 2 is an anode, 3 is a hole transport layer, 4 is an organic luminescent layer, 5 is an electron transport layer, and 6 is a cathode.
Detailed Description
The specific production method of the above-mentioned novel compound of the present invention will be described in detail below by taking a plurality of synthesis examples as examples, but the production method of the present invention is not limited to these synthesis examples.
Basic chemical raw materials of various chemicals used in the present invention, such as petroleum ether, tert-butylbenzene, ethyl acetate, sodium sulfate, toluene, dichloromethane, potassium carbonate, boron tribromide, N-diisopropylethylamine, reaction intermediate, and the like, are commercially available from shanghai tatarian technologies ltd and silong chemical ltd. The mass spectrometer used for determining the following compounds was a ZAB-HS type mass spectrometer measurement (manufactured by Micromass, UK).
In the following brief description of the method for synthesizing the compound of the present invention (scheme (1)), first, X is synthesized using a butyllithium reagent such as methyllithium, n-butyllithium, t-butyllithium and the like1And X2The hydrogen atoms in between undergo ortho-metallation. Subsequently, boron tribromide or the like is added to perform metal exchange of lithium-boron or lithium-phosphorus, and then Bronsted base (e.g., N-diisopropylethylamine) is added to perform a Tandem borohybrid-krafts Reaction (Tandem Bora-Friedel-Crafts Reaction), whereby the target compound can be obtained.
Y is Cl, Br or I; x1And X2Each independently is NR, and the R is selected from substituted or unsubstitutedOne of the following substituted groups: chain alkyl of C1-C30, cycloalkyl of C3-C30, haloalkyl of C1-C30, alkoxy of C1-C30, alkenyl of C2-C30, alkynyl of C3-C30, monocyclic aryl of C6-C60, fused ring aryl of C6-C60, aryloxy of C6-C60, monocyclic heteroaryl of C5-C60 or fused ring heteroaryl of C5-C60, and R can be bonded to an adjacent benzene ring by-O-, -S-, -C (-R) 2-or a single bond;
R1～R8each independently selected from hydrogen, deuterium, or one of the following substituted or unsubstituted groups: halogen, chain alkyl of C1-C30, cycloalkyl of C3-C30, alkoxy of C1-C10, thioalkoxy of C1-C10, carbonyl, carboxyl, nitro, cyano, amino, arylamino of C6-C30, heteroarylamino of C3-C30, monocyclic aryl of C6-C60, condensed ring aryl of C6-C60, aryloxy of C6-C60, monocyclic heteroaryl of C5-C60 or condensed ring heteroaryl of C5-C60, and R is R1～R20Wherein two adjacent groups can be bonded with each other to form one of a five-membered or six-membered aryl ring of C5-C30, a five-membered or six-membered heteroaryl ring of C5-C30, and at least one hydrogen in the formed ring can be substituted by any one of arylamino of C6-C30, heteroarylamino of C3-C30, monocyclic aryl of C6-C60, fused ring aryl of C6-C60, aryloxy of C6-C60, monocyclic heteroaryl of C5-C60, fused ring heteroaryl of C5-C60, halogen, chain alkyl of C1-C30, cycloalkyl of C3-C30, alkoxy of C1-C10, thioalkoxy of C1-C10, carbonyl, carboxyl, nitro, cyano, and amino;
more specifically, the following gives synthetic methods of representative compounds of the present invention.
Synthetic examples
Synthesis example 1: synthesis of Compound C-1
Under nitrogen, a solution of tert-butyllithium in pentane (18.96mL, 1.60M, 30.34mmol) was slowly added to 0 deg.C Br-substituted precursor (8.21g, 13.79mmol) in tert-butylbenzene (15)0mL) was added to the solution, and then the temperature was raised to 90 ℃ for 1 hour. After the reaction was complete, the temperature was reduced to-30 ℃ and boron tribromide (7.6g, 30.34mmol) was slowly added and stirring was continued at room temperature for 0.5 hour. N, N-diisopropylethylamine (5.35g, 41.37mmol) was added at room temperature and the reaction was continued at 125 ℃ for 5 hours and stopped. The solvent was dried by evaporation in vacuo and passed through a silica gel column (developing solvent: ethyl acetate: petroleum ether: 50:1) to give the title compound P-1(0.59g, 8% yield, HPLC assay purity 99.56%) as a green solid. MALDI-TOF-MS results: molecular ion peaks: 535.92, respectively; elemental analysis results: theoretical value (%):C,85.24；H,4.89；B,2.02；N,7.85(ii) a Experimental values (%):C,85.34；H,4.89；B,2.02； N,7.75。
synthesis example 2: synthesis of Compound C-3
This example is substantially the same as synthetic example 1 except that: in this case, the following steps are requiredC-1-1By equivalent amounts of substancesC-3-1. The title compound C-3(0.66g, 9% yield, 99.66% purity by HPLC) was a yellow solid. MALDI-TOF-MS results: molecular ion peaks:531.45；elemental analysis results: theoretical value (%):C,85.89；H,4.17；B, 2.03；N,7.91(ii) a Experimental values (%):C,85.79；H,4.27；B,2.04；N,7.90。
synthetic example 3: synthesis of Compound C-25
This example is substantially the same as synthetic example 1 except that: in this case, the following steps are requiredC-1-1By equivalent amounts of substancesC-25-1Will be provided withMethyl lithiumBy equivalent amounts of substancesTert-butyl lithium.The title compound C-25(0.48g, 6% yield, 99.46% analytical purity by HPLC) was a yellow solid. MALDI-TOF-MS results: molecular ion peaks:577.45；elemental analysis results: theoretical value (%):C,85.27；H,5.59；B,1.87；N,7.28(ii) a Fruit of Chinese wolfberryTest value (%):C,85.47；H,5.49；B,1.77； N,7.28。
synthetic example 4: synthesis of Compound C-27
This example is essentially the same as synthetic example 3, except that: in this case, the following steps are requiredC-25-1By equivalent amounts of substancesC-27-1. The title compound C-27(0.50g, 6% yield, 99.43% analytical purity by HPLC) was a yellow solid. MALDI-TOF-MS results: molecular ion peaks:573.55；elemental analysis results: theoretical value (%):C,85.87；H,4.92；B, 1.88；N,7.33(ii) a Experimental values (%):C,85.67；H,4.92；B,1.88；N,7.53。
synthesis example 5: synthesis of Compound C-77
This example is substantially the same as synthetic example 1 except that: in this case, the following steps are requiredC-1-1By equivalent amounts of substancesC-77-1Will be provided withMethyl lithiumChange to positive of equal amount of substanceButyl lithium.The title compound C-77(0.72g, 9% yield, 99.46% analytical purity by HPLC) was a yellow solid. MALDI-TOF-MS results: molecular ion peaks:577.48；elemental analysis results: theoretical value (%):C,85.27；H,5.59；B,1.87；N,7.28(ii) a Experimental values (%):C,85.47；H,5.49；B,1.87； N,7.28。
synthetic example 6: synthesis of Compound C-79
This example is substantially the same as synthetic example 5 except that: in this case, the following steps are requiredC-77-1By equivalent amounts of substancesC-79-1. C-79(0.76g, 9% yield, 99.74% purity by HPLC) was a yellow solid. MALDI-TOF-MS results: peak of molecular ion577.35；Elemental analysis results: theoretical value: theoretical value (%):C,85.27；H,5.59；B,1.87； N,7.28(ii) a Experimental values (%):C,85.47；H,5.39；B,1.97；N,7.28。
synthetic example 7: synthesis of Compound C-102
This example is substantially the same as synthetic example 1 except that: in this case, the following steps are requiredC-1-1By equivalent amounts of substancesC-102-1. The title compound C-102(0.48g, 6% yield, 98.66% analytical by HPLC) was a yellow solid. MALDI-TOF-MS results: molecular ion peaks:585.45；elemental analysis results: theoretical value (%):C,86.16；H,4.82； B,1.85；N,7.18(ii) a Experimental values (%):C,86.06；H,4.92；B,1.85；N,7.18。
synthesis example 8: synthesis of Compound C-103
This example is substantially the same as synthetic example 1 except that: in this case, the following steps are requiredC-1-1By equivalent amounts of substancesC-103-1. The title compound C-3(0.64g, 8% yield, 99.66% purity by HPLC) was a yellow solid. MALDI-TOF-MS results: molecular ion peaks:581.45；elemental analysis results: theoretical value (%):C,86.75；H,4.16；B, 1.86；N,7.23(ii) a Experimental values (%):C,86.65；H,4.26；B,1.86；N,7.23。
synthetic example 9: synthesis of Compound C-110
This example is substantially the same as synthetic example 1 except that: in this case, the following steps are requiredC-1-1By equivalent amounts of substancesC-110-1. TargetCompound C-110(0.63g, 8% yield, 99.66% purity by HPLC) was a yellow solid. MALDI-TOF-MS results: molecular ion peaks:574.45；elemental analysis results: theoretical value (%):C,83.63；H,4.74； B,1.88；N,9.75(ii) a Experimental values (%):C,83.73；H,4.74；B,1.88；N,9.65。
synthetic example 10: synthesis of Compound C-111
This example is substantially the same as synthetic example 1 except that: in this case, the following steps are requiredC-1-1By equivalent amounts of substancesC-111-1. The title compound C-111(0.67g, 9% yield, 99.23% purity by HPLC) was a yellow solid. MALDI-TOF-MS results: molecular ion peaks:569.67；elemental analysis results: theoretical value (%): MALDI-TOF-MS results: molecular ion peaks:570.45；elemental analysis results: theoretical value (%):C,84.22；H,4.06；B,1.89；N,9.82(ii) a Experimental values (%):C,84.32；H,4.16；B,1.89；N,9.62。
synthetic example 11: synthesis of Compound C-132
This example is substantially the same as synthetic example 1 except that: in this case, the following steps are requiredC-1-1By equivalent amounts of substancesC-132-1. The title compound C-132(0.60g, 8% yield, 99.46% analytical purity by HPLC) was a yellow solid. MALDI-TOF-MS results: molecular ion peak 535.72; elemental analysis results: theoretical value (%):C,85.24；H,4.89； B,2.02；N,7.85(ii) a Experimental values (%):C,85.34；H,4.86；B,2.05；N,7.75。
synthetic example 12: synthesis of Compound C-134
This example is substantially the same as synthetic example 1 except that: in this case, the following steps are requiredC-1-1By equivalent amounts of substancesC-134-1. The title compound C-134(0.70g, 9% yield, 99.33% analytical by HPLC) was an orange solid. MALDI-TOF-MS results: molecular ion peaks:521.76elemental analysis results: theoretical value:C,85.23％；H,4.64％； B,2.07％；N,8.06％(ii) a Experimental values:C,85.32％；H,4.55％；B,2.37％；N,7.76％。
synthetic example 13: synthesis of Compound C-156
This example is essentially the same as synthetic example 3, except that: in this case, the following steps are requiredC-25-1By equivalent amounts of substancesC-156-1. The title compound C-156(0.49g, 6% yield, 99.11% purity by HPLC) was a yellow solid. MALDI-TOF-MS results: molecular ion peaks:577.45；elemental analysis results: theoretical value (%):C,85.27；H,5.59； B,1.87；N,7.28(ii) a Experimental values (%):C,85.48；H,5.48；B,1.67；N,7.38。
synthesis example 14: synthesis of Compound C-158
This example is essentially the same as synthetic example 4, except that: in this case, the following steps are requiredC-27-1By equivalent amounts of substancesC-158-1. The title compound C-27(0.52g, 6% yield, 99.26% purity by HPLC) was a yellow solid. MALDI-TOF-MS results: molecular ion peaks:573.55；elemental analysis results: theoretical value (%):C,85.87；H,4.92；B, 1.88；N,7.33(ii) a Experimental values (%):C,85.77；H,4.92；B,1.88；N,7.33。
synthetic example 15: synthesis of Compound C-208
This example is substantially the same as synthetic example 5 except that: in this case, the following steps are requiredC-77-1By equivalent amounts of substancesC-208-1. Will be provided withMethyl lithiumChange to positive of equal amount of substanceButyl lithium.The title compound C-208(0.73g, 9% yield, 99.67% purity by HPLC) was a yellow solid. MALDI-TOF-MS results: molecular ion peaks:577.48；elemental analysis results: theoretical value (%):C,85.27；H,5.59；B,1.87；N,7.28(ii) a Experimental values (%):C,85.37；H,5.59；B, 1.86；N,7.29。
synthetic example 16: synthesis of Compound C-79
This example is substantially the same as synthetic example 5 except that: in this case, the following steps are requiredC-79-1By equivalent amounts of substancesC-210-1. C-79(0.77g, 9% yield, 99.24% purity by HPLC) was a yellow solid. MALDI-TOF-MS results: peak of molecular ion577.65；Elemental analysis results: theoretical value: theoretical value (%):C,85.27；H,5.59；B,1.87； N,7.28(ii) a Experimental values (%):C,85.44；H,5.42；B,1.97；N,7.28。
synthetic example 17: synthesis of Compound C-233
This example is substantially the same as synthetic example 1 except that: in this case, the following steps are requiredC-1-1By equivalent amounts of substancesC-233-1. The title compound C-233(0.47g, 6% yield, 99.16% analytical purity by HPLC) was a yellow solid. MALDI-TOF-MS results: molecular ion peaks:585.45；elemental analysis results: theoretical value (%):C,86.16；H,4.82； B,1.85；N,7.18(ii) a Experimental values (%):C,86.16；H,4.92；B,1.85；N,7.08。
synthetic example 18: synthesis of Compound C-234
This example is substantially the same as synthetic example 1 except that: in this case, the following steps are requiredC-1-1By equivalent amounts of substancesC-234-1. The title compound C-234(0.65g, 8% yield, 99.45% purity by HPLC) was a yellow solid. MALDI-TOF-MS results: molecular ion peaks:581.45；elemental analysis results: theoretical value (%):C,86.75；H,4.16； B,1.86；N,7.23(ii) a Experimental values (%):C,86.55；H,4.26；B,1.86；N,7.33。
synthetic example 19: synthesis of Compound C-252
This example is substantially the same as synthetic example 1 except that: in this case, the following steps are requiredC-1-1By equivalent amounts of substancesC-252-1. The title compound C-252(0.68g, 9% yield, 99.47% purity by HPLC) was a yellow solid. MALDI-TOF-MS results: molecular ion peaks:570.45；elemental analysis results: theoretical value (%):C,84.22；H,4.06； B,1.89；N,9.82(ii) a Experimental values (%):C,84.32；H,4.06；B,1.89；N,9.72。
synthesis example 20: synthesis of Compound C-244
This example is substantially the same as synthetic example 1 except that: in this case, the following steps are requiredC-1-1By equivalent amounts of substancesC-244-1. The title compound C-244(0.94g, 12% yield, 99.27% purity by HPLC) was a yellow solid. MALDI-TOF-MS results: molecular ion peaks:570.45；elemental analysis results: theoretical value (%):C,84.22；H,4.06； B,1.89；N,9.82(ii) a Experimental values (%):C,84.42；H,4.16；B,1.89；N,9.52。
the technical effects and advantages of the invention are shown and verified by testing practical use performance by specifically applying the compound of the invention to an organic electroluminescent device.
The organic electroluminescent device includes a first electrode, a second electrode, and an organic material layer between the two electrodes. The organic material may 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.
As a material of the anode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO2), or zinc oxide (ZnO), or any combination thereof can be used. The cathode may be made of magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination 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 containing only one compound and a single layer containing a plurality of compounds. The hole transport region may also be 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 polymers containing conductive dopants such as polyphenylenevinylene, 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, and the like.
The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra, 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 single color light emitting layers of a plurality of different colors may be arranged in a planar manner in accordance with a pixel pattern, or may be stacked 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 emitting red, green, blue, or the like at the same time.
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 preparation process of the organic electroluminescent device is described as follows with reference to the attached figure 1: an anode 2, a hole transport layer 3, an organic light emitting layer 4, an electron transport layer 5, and a cathode 6 are sequentially deposited on a substrate 1, and then encapsulated. In the preparation of the organic light-emitting layer 4, the organic light-emitting layer 4 is formed by a co-deposition method using a wide band gap material source, an electron donor material source, an electron acceptor material source, and a resonance TADF material source.
Specifically, the preparation method of the organic electroluminescent device comprises the following steps:
1. the anode material coated glass plate was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an 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 cationic beams;
2. placing the glass plate with the anode in a vacuum chamber, and vacuumizing to 1 × 10-5～9×10-3Pa, forming a hole injection layer by vacuum evaporation of a hole injection material on the anode layer film, wherein the evaporation rate is 0.1-0.5 nm/s;
3. vacuum evaporating hole transport material on the hole injection layer to form a hole transport layer with an evaporation rate of 0.1-0.5nm/s,
4. vacuum evaporating an electron blocking layer on the hole transport layer, wherein the evaporation rate is 0.1-0.5 nm/s;
5. the organic light-emitting layer of the device is vacuum evaporated on the electron barrier layer, the organic light-emitting layer material comprises a main material and TADF dye, and the evaporation rate of the main material, the evaporation rate of the sensitizer material and the evaporation rate of the dye are adjusted by a multi-source co-evaporation method to enable the dye to reach a preset doping proportion;
6. vacuum evaporating a hole blocking layer on the organic light-emitting layer, wherein the evaporation rate is 0.1-0.5 nm/s;
7. forming an electron transport layer on the hole blocking layer by vacuum evaporation of an electron transport material of the device, wherein the evaporation rate is 0.1-0.5 nm/s;
8. LiF is evaporated on the electron transport layer in vacuum at a speed of 0.1-0.5nm/s to serve as an electron injection layer, and an Al layer is evaporated on the electron transport layer in vacuum at a speed of 0.5-1nm/s to serve as a cathode of the device.
The embodiment of the invention also provides a display device which comprises the organic electroluminescent device provided as above. The display device can be specifically a display device such as an OLED display, and any product or component with a display function including the display device, such as a television, a digital camera, a mobile phone, a tablet computer, and the like. The display device has the same advantages as the organic electroluminescent device compared with the prior art, and the description is omitted here.
The organic electroluminescent device according to the invention is further illustrated by the following specific examples.
Device example 1
The structure of the organic electroluminescent device prepared in this example is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:3wt％C-3(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
wherein the anode material is ITO; the hole injection layer is made of HI, the total thickness is generally 5-30nm, and the thickness is 10nm in the embodiment; the hole transport layer is made of HT, and the total thickness is generally 5-500nm, 40nm in this embodiment; host is a main body material with wide band gap of an organic light-emitting layer, the compound C-3 is dye and the doping concentration is 3 wt%, the thickness of the organic light-emitting layer is generally 1-200nm, in this embodiment 30 nm; the material of the electron transport layer is ET, the thickness is generally 5-300nm, in this embodiment 30 nm; the electron injection layer and the cathode material are selected from LiF (0.5nm) and metallic aluminum (150 nm).
A DC voltage was applied to the organic electroluminescent element D1 prepared in this example, and 10cd/m was measured2The characteristics in light emission were such that green emission (driving voltage of 2.6V) with a wavelength of 525nm, a half-peak width of 34nm, CIE color coordinates (x, y) ═ 0.28,0.66, and external quantum efficiency EQE of 22.8% was obtained.
Device example 2
The same preparation method as that of the device example 1 except that the wide band gap type Host material used in the light emitting layer was replaced with the TADF type Host TD, the specific device structure was as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/TD:3wt％C-3(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D2 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m2The green emission (driving voltage of 2.4V) having a wavelength of 526nm, a half-peak width of 35nm, CIE color coordinates (x, y) (0.29,0.67), and an external quantum efficiency EQE of 31.4% was obtained as characteristics in the emission.
Device example 3
The same procedure as in device example 1 was followed except that the dye used in the light-emitting layer was replaced with C-27 from C-3. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:3wt％C-27(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D3 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m2The green emission (driving voltage of 2.6V) having a wavelength of 528nm, a half-width of 32nm, CIE color coordinates (x, y) ═ 0.27,0.69, and an external quantum efficiency EQE of 23.3% was obtained as characteristics in the emission.
Device example 4
The same preparation method as that of device example 1 was used except that the wide band gap type Host material Host in the light-emitting layer was replaced with TADF type Host TD and the dye was replaced with C-3 to C-27. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/TD:3wt％C-27(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D4 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m2The green emission (driving voltage of 2.4V) having a wavelength of 530nm, a half-width of 32nm, CIE color coordinates (x, y) (0.28,0.68), and an external quantum efficiency EQE of 30.4% was obtained as characteristics in the emission.
Device example 5
The same procedure as in device example 1 was followed except that the dye in the light-emitting layer was replaced with C-79 from C-3. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:3wt％C-79(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D5 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m2The green emission (driving voltage of 2.6V) having a wavelength of 528nm, a half-width of 30nm, CIE color coordinates (x, y) ═ 0.27,0.67, and an external quantum efficiency EQE of 22.3% was obtained as characteristics in the emission.
Device example 6
The same preparation method as that of device example 1 was used except that the wide band gap type Host material Host in the light-emitting layer was replaced with TADF type Host TD and the dye was replaced with C-79 from C-3. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/TD:3wt％C-79(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D6 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m2The green emission (driving voltage of 2.6V) having a wavelength of 527nm, a half-peak width of 32nm, CIE color coordinates (x, y) ═ 0.27,0.69, and an external quantum efficiency EQE of 33.6% was obtained as characteristics in the emission.
Device example 7
The same procedure as in device example 1 was followed except that the dye in the light-emitting layer was replaced with C-103 from C-3. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:3wt％C-103(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D7 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m2The characteristics in light emission were such that yellow light emission (driving voltage of 2.6V) having a wavelength of 545nm, a half-peak width of 36nm, CIE color coordinates (x, y) (0.36,0.55), and an external quantum efficiency EQE of 21.3% was obtained.
Device example 8
The same preparation method as that of device example 1 was used except that the wide band gap type Host material Host in the light-emitting layer was replaced with TADF type Host TD and the dye was replaced with C-3 to C-103. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/TD:3wt％C-103(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D8 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m2The characteristics in light emission were such that yellow light emission (drive voltage of 2.4V) having a wavelength of 547nm, a half-peak width of 40nm, CIE color coordinates (x, y) (0.37,0.54), and external quantum efficiency EQE of 27.4% was obtained.
Device example 9
The same procedure as in device example 1 was followed except that the dye in the light-emitting layer was replaced with C-111 instead of C-3. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:3wt％C-111(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D9 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m2The characteristics in light emission were such that red light emission (driving voltage of 2.6V) with a wavelength of 587nm, a half-peak width of 41nm, CIE color coordinates (x, y) ═ 0.45,0.54, and an external quantum efficiency EQE of 21.3% was obtained.
Device example 10
The same preparation method as that of device example 1 was used except that the wide band gap type Host material Host in the light-emitting layer was replaced with TADF type Host TD and the dye was replaced with C-111 from C-3. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/TD:3wt％C-111(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D10 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m2The characteristics in light emission were such that red emission (driving voltage of 2.4V) with a wavelength of 588nm, a half-width of 42nm, CIE color coordinates (x, y) ═ 0.46,0.53, and an external quantum efficiency EQE of 31.4% was obtained.
Device example 11
The same procedure as in device example 1 was followed except that the dye in the light-emitting layer was replaced with C-134 from C-3. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:3wt％C-134(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D11 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m2The characteristics in light emission were such that green emission (driving voltage of 2.6V) with a wavelength of 525nm, a half-peak width of 33nm, CIE color coordinates (x, y) ═ 0.26,0.64, and external quantum efficiency EQE of 23.0% was obtained.
Device example 12
The same preparation method as that of device example 1 was used except that the wide band gap type Host material Host in the light-emitting layer was replaced with TADF type Host TD and the dye was replaced with C-134 from C-3. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/TD:3wt％C-134(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D12 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m2The green emission (driving voltage of 2.4V) having a wavelength of 527nm, a half-peak width of 32nm, CIE color coordinates (x, y) (0.27,0.65), and an external quantum efficiency EQE of 30.4% was obtained as characteristics in the emission.
Device example 13
The same procedure as in device example 1 was followed, except that the dye in the light-emitting layer was replaced with C-158 from C-3. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:3wt％C-158(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D13 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m2The green emission (driving voltage of 2.6V) having a wavelength of 528nm, a half-width of 32nm, CIE color coordinates (x, y) ═ 0.29,0.66, and an external quantum efficiency EQE of 21.4% was obtained as characteristics in the emission.
Device example 14
The same preparation method as that of device example 1 was used except that the wide band gap type Host material Host in the light-emitting layer was replaced with TADF type Host TD and the dye was replaced with C-158 from C-3. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/TD:3wt％C-158(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D14 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m2The characteristics in light emission were such that green emission (driving voltage of 2.4V) having a wavelength of 526nm, a half-peak width of 33nm, CIE color coordinates (x, y) (0.29,0.68), and external quantum efficiency EQE of 29.4% was obtained.
Device example 15
The same procedure as in device example 1 was followed except that the dye in the light-emitting layer was replaced with C-210 from C-3. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/Host:3wt％C-210(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D15 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m2The green emission (driving voltage of 2.6V) having a wavelength of 527nm, a half-peak width of 32nm, CIE color coordinates (x, y) (0.25,0.68), and an external quantum efficiency EQE of 21.6% was obtained as characteristics in the emission.
Device example 16
The same preparation method as that of device example 1 was used except that the wide band gap type Host material Host in the light-emitting layer was replaced with TADF type Host TD and the dye was replaced with C-210 from C-3. The device structure is as follows:
ITO/HI(10nm)/HT(30nm)/EBL(10nm)/TD:3wt％C-210(30nm)/HBL(10nm)ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device D16 prepared in this example were as follows: applying a DC voltage, and measuring 10cd/m2The green emission (driving voltage of 2.4V) having a wavelength of 526nm, a half-peak width of 33nm, CIE color coordinates (x, y) (0.25,0.70), and an external quantum efficiency EQE of 31.3% was obtained as characteristics in the emission.
Comparative device example 1
The same preparation method as that of device example 1 was followed except that the compound C-3 of the present invention used in the light-emitting layer was replaced with the compound P1 of the prior art, and the specific device structure was as follows:
ITO/HI(10nm)/HT(40nm)/Host:3wt％P1(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device DD1 prepared in this example are as follows: when a dc voltage was applied and the characteristics at 10cd/m2 light emission were measured, blue light emission (driving voltage of 3.6V) with a wavelength of 459nm, a full width at half maximum of 28nm, CIE color coordinates (x, y) ((0.13, 0.09)) and an external quantum efficiency EQE of 13.5% was obtained.
Comparative device example 2
The same preparation method as that of device example 2 except that the compound C-3 of the present invention used in the light-emitting layer was replaced with the compound P1 of the prior art, and a specific device structure was as follows:
ITO/HI(10nm)/HT(40nm)/TD:3wt％P1(30nm)/ET(30nm)/LiF(0.5nm)/Al(150nm)
the device performance results of the organic electroluminescent device DD2 prepared in this example are as follows: applying a DC voltage, and measuring 10cd/m2The characteristics in light emission were such that blue light emission (drive voltage of 3.3V) having a wavelength of 460nm, a peak width at half maximum of 28nm, CIE color coordinates (x, y) (0.13,0.09), and external quantum efficiency EQE of 18.4% was obtained.
The structural formulas of the various organic materials used in the above examples are as follows:
specific performance data of the organic electroluminescent devices D1 to D16 and the devices DD1 and DD2 prepared in the above respective device examples are detailed in table 1 below.
Table 1:
the experimental data show that the compound provided by the invention can realize the obvious red shift behavior of the target MR-TADF material while maintaining the large HOMO and LUMO orbital overlap of BN rigid framework by amplifying the conjugated framework of the classical MR-TADF material and introducing more nitrogen atoms or boron atoms. As can be seen from the half-peak width of the electroluminescence spectrum, the embodiment confirms that the material has effective multiple resonance effect, thereby greatly enriching the material system of multiple resonance-thermal activation delayed fluorescence and the range of luminescent color, and having good application prospect.
Although the invention has been described in connection with the embodiments, the invention is not limited to the embodiments described above, and it should be understood that various modifications and improvements can be made by those skilled in the art within the spirit of the invention, and the scope of the invention is outlined by the appended claims.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.
The experimental data show that the novel MR-TADF material provided by the invention has high color purity and high luminous efficiency, and can realize full spectrum emission from green light to red light under the electroluminescent condition after being prepared and applied to an organic electroluminescent device, thereby being an organic luminescent functional material with good performance and being expected to be popularized and commercialized.
Although the invention has been described in connection with the embodiments, the invention is not limited to the embodiments described above, and it should be understood that various modifications and improvements can be made by those skilled in the art within the spirit of the invention, and the scope of the invention is outlined by the appended claims.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.
Claims (10)
1. A compound of the formula (1):
in formula (1): ring A represents a ring simultaneously with the groups B and X, respectively1From B and X2A group formed by fusing and connecting six-membered ring structures, wherein the ring A is selected from one of a substituted or unsubstituted monocyclic nitrogen heteroaromatic ring of C5-C60 and a substituted or unsubstituted fused nitrogen heteroaromatic ring of C5-C60; preferably, ring A represents one of a substituted or unsubstituted monocyclic nitrogen heteroaromatic ring of C13-C60, a substituted or unsubstituted fused nitrogen heteroaromatic ring of C13-C60;
said X1And X2Each independently selected from NR, wherein R may be bonded to an adjacent benzene ring by-O-, -S-, -C (-R') 2-, or a single bond, and each independently selected from one of the following substituted or unsubstituted groups: chain alkyl of C1-C30, cycloalkyl of C3-C30, haloalkyl of C1-C30, alkoxy of C1-C30, alkenyl of C2-C30, alkynyl of C3-C30, monocyclic aryl of C6-C60, fused ring aryl of C6-C60, aryloxy of C6-C60, monocyclic heteroaryl of C5-C60 or fused ring heteroaryl of C5-C60;
the R is1～R8Each independently selected from hydrogen, deuterium, or one of the following substituted or unsubstituted groups: halogen, chain alkyl of C1-C30, cycloalkyl of C3-C30, alkoxy of C1-C10, thioalkoxy of C1-C10, carbonyl, carboxyl, nitro, cyano, amino, arylamino of C6-C30, heteroarylamino of C3-C30, monocyclic aryl of C6-C60, condensed ring aryl of C6-C60, aryloxy of C6-C60, monocyclic heteroaryl of C5-C60 or condensed ring heteroaryl of C5-C60, and R is R1～R20Wherein two adjacent groups can be bonded with each other to form one of a five-membered or six-membered aryl ring of C5-C30, a five-membered or six-membered heteroaryl ring of C5-C30, and at least one hydrogen in the formed ring can be substituted by any one of arylamino of C6-C30, heteroarylamino of C3-C30, monocyclic aryl of C6-C60, fused ring aryl of C6-C60, aryloxy of C6-C60, monocyclic heteroaryl of C5-C60, fused ring heteroaryl of C5-C60, halogen, chain alkyl of C1-C30, cycloalkyl of C3-C30, alkoxy of C1-C10, thioalkoxy of C1-C10, carbonyl, carboxyl, nitro, cyano, and amino;
when the above groups have substituents, the substituents are respectively and independently one selected from deuterium, halogen, cyano, chain alkyl of C1-C30, cycloalkyl of C3-C30, alkoxy of C1-C10, arylamino of C6-C30, heteroarylamino of C3-C30, aryl of C6-C30 and heteroaryl of C3-C30.
2. A compound of formula (i) according to claim 1, wherein ring a has the structure according to formula a1 or a 2:
in the formula A1, Y1～Y3Each independently selected from N or CR1, and Y1～Y3At least one of which is N; the R1 is selected from one of hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, substituted or unsubstituted C1-C10 silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl; two adjacent R1 can be fused to form a ring;
in formula A1, ring D is represented by the formulae B and Y1And Y2A group formed by fusing and connecting six-membered ring structures, wherein the ring D is selected from one of substituted or unsubstituted C6-C60 monocyclic aryl, substituted or unsubstituted C6-C60 fused ring aryl, substituted or unsubstituted C6-C60 aryloxy, substituted or unsubstituted C5-C60 monocyclic heteroaryl and substituted or unsubstituted C5-C60 fused ring heteroaryl;
in the formula A2, Z1～Z7Each independently selected from N or CR2, and Z1～Z7At least one of which is N; the R2 is selected from one of hydrogen substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C1-C10 alkoxy, halogen, cyano, nitro, hydroxyl, substituted or unsubstituted C1-C10 silyl, amino, substituted or unsubstituted C6-C30 arylamino, substituted or unsubstituted C3-C30 heteroarylamino, substituted or unsubstituted C6-C30 aryl and substituted or unsubstituted C3-C30 heteroaryl; two adjacent R2 s may be fused together to form a ring.
3. The compound of general formula (la) 1, wherein the ring D is selected from substituted or unsubstituted groups selected from any one of halogen, chain alkyl of C1-C30, cycloalkyl of C3-C30, alkoxy of C1-C10, thioalkoxy of C1-C10, carbonyl, carboxyl, nitro, cyano and amino:
4. a compound of formula A1 in accordance with claim 2, wherein Y is1Or Y2At least one of them is N, said Y3Selected from N or CR 1;
or in formula A1, Y1Is N, said Y2、Y3Each is independently selected from N or CR 1;
or in formula A1, Y2Is N, said Y1、Y3Each is independently selected from N or CR 1;
or in formula A1, Y1Is N, said Y2、Y3Are all selected from CR 1;
or in formula A1, Y2Is N, said Y1、Y3Are all selected from CR 1;
in the formula A2, Z1～Z7At least two of which are N;
or in formula A2, Z1、Z2、Z6And Z7At least one of which is N, said Z3～Z5Each is independently selected from N or CR 2;
or in formula A2, Z1、Z2、Z6And Z7At least two of which are N, said Z3～Z5Each is independently selected from N or CR 2;
or in formula A2, Z1And Z7Is N, said Z2～Z6Are all selected from CR 2;
or in formula A2, Z2And Z7Is N, said Z1、Z3～Z6Are all selected from CR 2;
or in formula A2, Z2And Z6Is N, saidZ1、Z3～Z5、Z7Are all selected from CR 2.
Or in formula A2, Z2Is N, said Z1、Z3～Z7Are all selected from CR 2.
5. A compound of general formula (la) according to claim 1, having a structure as shown in any one of the following formulae (2) to (6):
in formulae (2) to (6): x1、X2Are all as defined in formula (1);
the R is1、R2、R3、R4、R5、R5、R7、R8、R9、R10、R12、R13And R14Each independently selected from hydrogen, deuterium, or one of the following substituted or unsubstituted groups: halogen, chain alkyl of C1-C30, cycloalkyl of C3-C30, alkoxy of C1-C10, thioalkoxy of C1-C10, carbonyl, carboxyl, nitro, cyano, amino, arylamino of C6-C30, heteroarylamino of C3-C30, monocyclic aryl of C6-C60, condensed ring aryl of C6-C60, aryloxy of C6-C60, monocyclic heteroaryl of C5-C60 or condensed ring heteroaryl of C5-C60, and R is R1～R20Wherein adjacent two groups can be bonded with each other to form one of a five-or six-membered aryl ring of C5-C30, a five-or six-membered heteroaryl ring of C5-C30, and at least one hydrogen in the formed ring can be replaced by arylamino of C6-C30, heteroarylamino of C3-C30, monocyclic aryl of C6-C60, fused ring aryl of C6-C60, aryloxy of C6-C60, monocyclic heteroaryl of C5-C60, fused ring heteroaryl of C5-C60, halogen, chain alkyl of C1-C30, chain alkyl of C3-C30Cycloalkyl, alkoxy of C1-C10, thioalkoxy of C1-C10, carbonyl, carboxyl, nitro, cyano and amino;
when the above groups have substituents, the substituents are respectively and independently one selected from deuterium, halogen, cyano, chain alkyl of C1-C30, cycloalkyl of C3-C30, alkoxy of C1-C10, arylamino of C6-C30, heteroarylamino of C3-C30, aryl of C6-C30 and heteroaryl of C3-C30.
6. A compound of general formula (la) according to claim 5, wherein in formula (2):
the R is12And R13Or said R is10And R11One of five-or six-membered aryl rings of C5 to C30, five-or six-membered heteroaryl rings of C5 to C30, bonded to each other and taken together with the adjacent benzene ring, and at least one hydrogen in the formed rings may be substituted by any one of arylamino of C6 to C30, heteroarylamino of C3 to C30, monocyclic aryl of C6 to C60, fused-ring aryl of C6 to C60, aryloxy of C6 to C60, monocyclic heteroaryl of C5 to C60, fused-ring heteroaryl of C5 to C60, halogen, chain alkyl of C1 to C30, cycloalkyl of C3 to C30, alkoxy of C1 to C10, thioalkoxy of C1 to C10, carbonyl, carboxyl, nitro, cyano, or amino; more preferably, said R is12And R13Or said R is10And R11Bonded to each other and forming, together with the adjacent benzene ring, any of the following substituted or unsubstituted groups: naphthyl, anthracenyl, benzanthracenyl, phenanthrenyl, benzophenanthrenyl, pyrenyl, fluoranthenyl, tetracenyl, pentacenyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl;
in the formula (3):
the R is12And R13Or said R is10And R11Bonded to each other and form one of a five-or six-membered aryl ring of C5-C30 and a five-or six-membered heteroaryl ring of C5-C30 together with the adjacent benzene ringAnd at least one hydrogen in the formed ring can be substituted by any one of arylamino of C6-C30, heteroaryl of C3-C30, monocyclic aryl of C6-C60, condensed ring aryl of C6-C60, aryloxy of C6-C60, monocyclic heteroaryl of C5-C60, condensed ring heteroaryl of C5-C60, halogen, chain alkyl of C1-C30, cycloalkyl of C3-C30, alkoxy of C1-C10, thioalkoxy of C1-C10, carbonyl, carboxyl, nitro, cyano and amino; more preferably, said R is12And R13Or said R is10And R11Bonded to each other and forming, together with the adjacent benzene ring, any of the following substituted or unsubstituted groups: naphthyl, anthracenyl, benzanthracenyl, phenanthrenyl, benzophenanthrenyl, pyrenyl, fluoranthenyl, tetracenyl, pentacenyl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl.
7. Compound of general formula (la) according to claim 5 or 6, wherein in formulae (2) to (6):
said R1～R14Each independently selected from hydrogen, deuterium, or one of the following substituted or unsubstituted groups: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2, 2-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzanthryl, phenanthryl, benzophenanthryl, pyrenyl, grottoyl, perylenyl, anthrylenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, idophenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenylenyl, trimeric indenyl, isotridecylinyl, trimeric spiroindenyl, spiromesityl, spiroisotridecylinyl, furanyl, isobenzofuranyl, phenyl, terphenyl, anthryl, terphenyl, pyrenyl, terphenyl, terp, Dibenzofuranyl, thienyl, benzothienyl, isobenzothiopheneA phenyl group, a dibenzothienyl group, a pyrrolyl group, an isoindolyl group, a carbazolyl group, an indenocarbazyl group, a pyridyl group, a quinolyl group, an isoquinolyl group, an acridinyl group, a phenanthridinyl group, a benzo-5, 6-quinolyl group, a benzo-6, 7-quinolyl group, a benzo-7, 8-quinolyl group, a pyrazolyl group, an indazolyl group, an imidazolyl group, a benzimidazolyl group, a naphthoimidazolyl group, a phenanthrimidazolyl group, a pyridoimidazolyl group, a pyrazinoyl group, a quinoxaloyl group, an oxazolyl group, a naphthooxazolyl group, an anthracenyl group, a phenanthrenyl group, a1, 2-thiazolyl group, a1, 3-thiazolyl group, a benzothiazolyl group, a pyridazinyl group, a pyrimidyl group, a benzopyrimidinyl group, a quinoxalyl group, a1, 5-diazaanthrylyl group, a2, 7, 1, 6-diazenylene group, 1, 8-diazenylene group, 4,5,9, 10-tetraazaperylene group, pyrazinyl group, phenazinyl group, phenothiazinyl group, naphthyridinyl group, azacarbazolyl group, benzocarbazinyl group, phenanthrolinyl group, 1,2, 3-triazolyl group, 1,2, 4-triazolyl group, benzotriazolyl group, 1,2, 3-oxadiazolyl group, 1,2, 4-oxadiazolyl group, 1,2, 5-oxadiazolyl group, 1,2, 3-thiadiazolyl group, 1,2, 4-thiadiazolyl group, 1,2, 5-thiadiazolyl group, 1,3, 4-thiadiazolyl group, 1,3, 5-triazinyl group, 1,2, 4-triazinyl group, 1,2, 3-triazinyl group, tetrazolyl group, 1,2,4, 5-tetrazinyl group, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, 9-dimethylazinyl, triarylamino, adamantane, fluorophenyl, methylphenyl, trimethylphenyl, cyanophenyl, tetrahydropyrrole, piperidine, methoxy, silyl, or a combination of two substituents selected from the above;
and R is1～R14Wherein adjacent two groups can be bonded with each other to form one of a five-membered or six-membered aryl ring of C5-C30, a five-membered or six-membered heteroaryl ring of C5-C30, and at least one hydrogen in the formed ring can be replaced by arylamino of C6-C30, heteroarylamino of C3-C30, monocyclic aryl of C6-C60, fused ring aryl of C6-C60, aryloxy of C6-C60, monocyclic heteroaryl of C5-C60, fused ring heteroaryl of C5-C60, halogen, chain alkyl of C1-C30, cycloalkyl of C3-C30, alkoxy of C1-C10, thioalkoxy of C1-C10, carbonyl, carboxyl, nitro, cyano, or the likeAny one of the group and the amino group.
8. A compound of formula (la) according to claim 1, selected from the compounds of the following specific structures:
9. use of a compound as claimed in any one of claims 1 to 8 as a light-emitting layer material in an organic electroluminescent device.
10. An organic electroluminescent device comprising a first electrode, a second electrode and one or more organic functional layers interposed between said first and second electrodes, characterized in that said organic functional layers comprise at least one compound according to any one of claims 1 to 8;
preferably, the organic functional layer comprises a hole transport region, a light emitting layer and an electron transport region, the hole transport region is formed on the anode layer, the cathode layer is formed on the electron transport region, and the light emitting layer is arranged between the hole transport region and the electron transport region; wherein the light-emitting layer comprises the compound of any one of claims 1 to 8.
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