CN118271187A - Compound for organic electroluminescent device, application of compound and organic electroluminescent device - Google Patents
Compound for organic electroluminescent device, application of compound and organic electroluminescent deviceInfo
- Publication number
- CN118271187A CN118271187A CN202211728289.XA CN202211728289A CN118271187A CN 118271187 A CN118271187 A CN 118271187A CN 202211728289 A CN202211728289 A CN 202211728289A CN 118271187 A CN118271187 A CN 118271187A
- Authority
- CN
- China
- Prior art keywords
- substituted
- unsubstituted
- aryl
- group
- heteroaryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 53
- 125000001424 substituent group Chemical group 0.000 claims abstract description 25
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims abstract description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 125000000732 arylene group Chemical group 0.000 claims abstract description 3
- 125000005549 heteroarylene group Chemical group 0.000 claims abstract description 3
- -1 amine compound Chemical class 0.000 claims description 151
- 239000010410 layer Substances 0.000 claims description 85
- 239000000463 material Substances 0.000 claims description 44
- 230000000903 blocking effect Effects 0.000 claims description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical group 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 230000005525 hole transport Effects 0.000 claims description 14
- 238000002347 injection Methods 0.000 claims description 12
- 239000007924 injection Substances 0.000 claims description 12
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 8
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 8
- 239000002346 layers by function Substances 0.000 claims description 8
- 239000010409 thin film Substances 0.000 claims description 7
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 6
- 125000001769 aryl amino group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 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 4
- 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 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 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 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 230000005669 field effect Effects 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 3
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000005516 engineering process Methods 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 125000001624 naphthyl group Chemical group 0.000 description 9
- 239000011368 organic material Substances 0.000 description 8
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 7
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000005401 electroluminescence Methods 0.000 description 7
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 7
- 239000002019 doping agent Substances 0.000 description 6
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 6
- 239000002356 single layer Substances 0.000 description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical group [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
- 125000001544 thienyl group Chemical group 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 5
- 125000001725 pyrenyl group Chemical group 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 4
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 3
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000005286 illumination Methods 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 3
- 125000005561 phenanthryl group Chemical group 0.000 description 3
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 3
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 125000000168 pyrrolyl group Chemical group 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 2
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 2
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 description 2
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 2
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 2
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 2
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 description 2
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 2
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 description 2
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 description 2
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 2
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- BAJWPRYGXIMFCY-UHFFFAOYSA-N 2-chloro-1,3-bis[2,6-di(propan-2-yl)phenyl]-2h-imidazole Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N1C(Cl)N(C=2C(=CC=CC=2C(C)C)C(C)C)C=C1 BAJWPRYGXIMFCY-UHFFFAOYSA-N 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229910052769 Ytterbium Inorganic materials 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 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 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 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 239000012761 high-performance material Substances 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 2
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 125000005990 isobenzothienyl group Chemical group 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 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 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 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 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 125000002098 pyridazinyl group Chemical group 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 2
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 2
- 125000003831 tetrazolyl group Chemical group 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
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Abstract
The present invention provides a compound for an organic electroluminescent device, characterized in that it comprises a compound having a structure represented by formula (I)Ar 1 is substituted or unsubstituted C8-C60 aryl, substituted or unsubstituted C8-C60 heteroaryl; ar 2、Ar3 is independently a substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; l 1,L2 is a single bond, a substituted or unsubstituted C6-C30 arylene, or a substituted or unsubstituted C3-C30 heteroarylene; r is a substituent, wherein at least one R is methyl.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a compound for an organic electroluminescent device and the organic electroluminescent device.
Background
An organic electroluminescent device (OLED: organic Light Emission Diodes) is a device with a sandwich-like structure, comprising positive and negative electrode layers and an organic functional material layer sandwiched between the electrode layers. And applying voltage to the electrode of the OLED device, injecting positive charges from the positive electrode, injecting negative charges from the negative electrode, and transferring and meeting the positive charges and the negative charges in the organic layer to emit light compositely under the action of an electric field. Because the OLED device has the advantages of high brightness, quick response, wide viewing angle, simple process, flexibility and the like, the OLED device has a great deal of attention in the novel display technical field and the novel illumination technical field. At present, the technology is widely applied to display panels of products such as novel illumination lamps, smart phones and tablet computers, and further expands the application field of large-size display products such as televisions, and is a novel display technology with rapid development and high technical requirements.
With the continuous advancement of the OLED in the two fields of illumination and display, the research on the core materials of the OLED is also more focused. This is because an efficient, long-life OLED device is typically the result of an optimized match of device structures and various organic materials, which provides great opportunities and challenges for chemists to design and develop functionalized materials of various structures. Common functionalized organic materials are: a hole injecting material, a hole transporting material, a hole blocking material, an electron injecting material, an electron transporting material, an electron blocking material, a light emitting host material, a light emitting guest (dye), and the like.
In order to prepare the OLED light-emitting device with lower driving voltage, better light-emitting efficiency and longer service life of the device, the performance of the OLED device is continuously improved, the structure and the manufacturing process of the OLED device are required to be innovated, and the photoelectric functional material in the OLED device is required to be continuously researched and innovated so as to prepare the functional material with higher performance. Based on this, the OLED materials community has been striving to develop new organic electroluminescent materials to achieve low starting voltage, high luminous efficiency and better lifetime of the device. In recent years, industry people continuously try and search for improving the efficiency and stability of devices, wherein a mode of seeking new materials to improve the performance of the devices is mainly adopted, a large number of novel materials are developed and applied to the organic electroluminescent devices, and the devices are improved to a certain extent, but the problems of accumulating a large amount of carriers at interfaces and being lower in device efficiency still exist.
Therefore, there is a need in the art to develop organic electroluminescent devices with higher performance, and further develop organic electroluminescent materials capable of providing better photoelectric performance, especially electron blocking materials, are the direction of continuous efforts in the industry to break through.
Disclosure of Invention
In view of the shortcomings of the prior art, it is an object of the present invention to provide a compound which can be used as an electron blocking layer material in an organic electronic device, an electronic device using the same has high luminous efficiency and low starting voltage, and the lifetime is greatly improved. To achieve the object, the present inventors have intensively studied to develop the following technical means to complete the present invention.
Specifically, the present invention provides an aryl-substituted amine compound characterized by being a compound having a structure represented by the formula (I):
Ar 1 is one of a substituted or unsubstituted C8-C60 aryl group, a substituted or unsubstituted C8-C60 heteroaryl group in formula (I); l 1、L2 is independently selected from one of single bond, substituted or unsubstituted C6-C30 arylene, and substituted or unsubstituted C3-C30 heteroarylene; ar 2、Ar3 is independently selected from one of substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl; r is selected from halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C2-C8 alkenyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; m is an integer from 1 to 6, provided that at least one R is methyl; each R is the same or different and R is optionally fused to or not to an adjacent group, preferably R is not fused to an adjacent group; the substituents in each of the above substituted or unsubstituted groups are each independently selected from one or a combination of at least two of halogen, C1-C20 straight or branched chain alkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl; the expression "ring structure" indicates that the linking site is located at any position on the ring structure that is capable of bonding.
The compound of the invention can effectively reduce the driving voltage of the device when being used as an electron blocking material, improve the luminous efficiency of the device, and is considered to be helpful for improving the service life characteristic according to the comparative test in the embodiment. The reason for this is not clear, and the following reasons are presumed:
The triaryl substituted amine compound has strong hole transport capability and is suitable for electron blocking, and the inventor discovers that if the conjugated system of the aromatic group is larger, the flatness of the whole molecule is better, and the hole transport is facilitated, which is possibly related to a film forming structure after evaporation, in the N substituted group, ar 1 is defined as an aromatic group (aromatic group above C8) with a larger conjugated system in the invention; in the invention, when at least one methyl substituent exists in the naphthyl of the mother nucleus, the service life of the device is greatly improved, the steric hindrance of the methyl is possibly proper, and the whole molecule is in a moderate plane effect from the space three-dimensional structure, so that the film forming effect is good, and the service life is prolonged.
In the present specification, the expression of Ca to Cb means that the group has a carbon number of a to b, and unless otherwise specified, the carbon number generally does not include the carbon number of a substituent. For example, C1 to C10 represent C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, and intermediate numerals are also described in the present invention.
In the present invention, unless otherwise specified, the expression of chemical elements generally includes the concept of isotopes having the same chemical properties, for example, the expression of "hydrogen" includes the concept of deuterium and tritium having the same chemical properties, and carbon (C) includes 12C、13 C and the like, and will not be described again.
In the formulae disclosed in the present specification, the expression of the ring structure "to which" - "is drawn indicates that the linking site is located at any position on the ring structure that is capable of bonding.
In the present specification, unless otherwise specified, both aryl and heteroaryl include cases of single rings and condensed rings. By monocyclic aryl is meant that the molecule contains at least one phenyl group, and when the molecule contains at least two phenyl groups, the phenyl groups are independent of each other and are linked by a single bond, such as phenyl, biphenyl, terphenyl, and the like; condensed ring aryl means that the molecule contains at least two benzene rings, but the benzene rings are not independent of each other, but the common ring edges are condensed with each other, such as naphthyl, anthracenyl and the like; monocyclic heteroaryl means that the molecule contains at least one heteroaryl group, and when the molecule contains one heteroaryl group and other groups (such as aryl, heteroaryl, alkyl, etc.), the heteroaryl group and the other groups are independent of each other and are connected by a single bond, such as pyridine, furan, thiophene, etc.; condensed ring heteroaryl means fused from at least one phenyl group and at least one heteroaryl group, or fused from at least two heteroaryl rings, such as, for example, quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, and the like
In the present specification, the substituted or unsubstituted C6 to C60 aryl group is preferably a C6 to C30 aryl group, more preferably a group selected from the group consisting of phenyl, naphthyl, anthryl, benzanthrenyl, phenanthryl, benzophenanthryl, pyrenyl, hole, perylenyl, fluoranthenyl, naphthacene, pentacenyl, benzopyrenyl, biphenyl, terphenyl, tetraphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis or trans indenofluorenyl, trimeriindenyl, heterotrimeric indenyl, spirotrimeric indenyl, spiroheterotrimeric indenyl. Specifically, the biphenyl group is selected from the group consisting of 2-biphenyl group, 3-biphenyl group and 4-biphenyl group; terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl comprises 1-naphthyl or 2-naphthyl; the anthracenyl is selected from the group consisting of 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; and the tetracenyl is selected from the group consisting of 1-tetracenyl, 2-tetracenyl and 9-tetracenyl. Preferred examples of the aryl group in the present invention include a group selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, indenyl, fluorenyl and derivatives thereof, fluoranthenyl, triphenylenyl, pyrenyl, perylenyl,A group selected from the group consisting of a radical and a tetracenyl radical. The biphenyl is selected from 2-biphenyl, 3-biphenyl and 4-biphenyl; the terphenyl group comprises p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl comprises 1-naphthyl or 2-naphthyl; the anthracenyl is selected from the group consisting of 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the fluorenyl derivative is selected from the group consisting of 9, 9-dimethylfluorene, 9-spirobifluorene and benzofluorene; the pyrenyl group is selected from the group consisting of 1-pyrenyl, 2-pyrenyl, and 4-pyrenyl; the tetracenyl group is selected from the group consisting of 1-tetracenyl, 2-tetracenyl and 9-tetracenyl. The C6-C60 aryl group of the present invention may be a group in which the above groups are bonded by single bonds or/and condensed.
Heteroatoms in the present invention are generally selected from N, O, S, P, si and Se, preferably from N, O, S.
In the present specification, the substituted or unsubstituted C3 to C60 heteroaryl group is preferably a C3 to C30 heteroaryl group, more preferably a C8 to C30 heteroaryl group, still more preferably a nitrogen-containing heteroaryl group, an oxygen-containing heteroaryl group, a sulfur-containing heteroaryl group, or the like, and specific examples thereof include: furyl, thienyl, pyrrolyl, pyridyl, benzofuryl, benzothienyl, isobenzofuryl, isobenzothienyl, indolyl, isoindolyl, dibenzofuryl, dibenzothienyl, carbazolyl, derivatives thereof, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolinyl, benzo-6, 7-quinolinyl, benzo-7, 8-quinolinyl, phenothiazinyl, phenazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthyridinyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, thienyl, benzoxazolyl, naphthyridinyl, anthracenooxazolyl, phenanthroizolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthracenyl, 2,7, 2,3, 6, 4-dipyrene, 1, 4-dipyrene, 4, 5-dipyrene, 10-tetraazaperylene, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarboline, phenanthroline, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazole, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazole, and the like. As preferable examples of the heteroaryl group in the present invention, for example, furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, isobenzofuryl, indolyl, dibenzofuryl, dibenzothienyl, carbazolyl and derivatives thereof are mentioned, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole benzocarbazole, dibenzocarbazole or indolocarbazole. The C3-C60 heteroaryl groups of the present invention may also be those wherein the above groups are joined singly or in combination by fusion. In the present invention, the C3-C60 heteroaryl group is most preferably carbazolyl group and its derivatives.
In the present specification, the term alkyl includes the concept of cycloalkyl, and cycloalkyl is not included if chain alkyl is emphasized. Examples of the C1-C30 alkyl group include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, cyclopentyl, neopentyl, n-hexyl, cyclohexyl, adamantyl, neohexyl, n-heptyl, cycloheptyl, n-octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2-trifluoroethyl and the like. The C1-C30 alkyl group is preferably a C1-C12 alkyl group, more preferably a C1-C10 alkyl group, and still more preferably a C1-C6 alkyl group.
In the present specification, cycloalkyl includes monocycloalkyl and multicycloalkyl, and may be, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like.
In the present specification, examples of the C1 to C30 alkoxy group include: methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy, isopentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy and the like are preferred, methoxy, ethoxy, n-propoxy, isopropoxy, tert-butoxy, sec-butoxy, isobutoxy, isopentyloxy are more preferred.
In the present specification, examples of the C1-C30 silyl group include silyl groups substituted with the groups exemplified for the C1-C30 alkyl groups, and specific examples include: and methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, t-butyldimethylsilyl, t-butyldiphenylsilyl, and the like.
In the present specification, examples of halogen include: fluorine, chlorine, bromine, iodine, and the like.
More specifically, as the above-mentioned R group, preferably, 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-trifluoroethyl, phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthryl, benzophenanthryl, pyrenyl, hole-yl, perylene, fluoranthenyl, naphthacene, pentacenyl, benzopyrene, biphenyl, even phenyl, terphenyl, triphenyl, tetrabenzoyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, trimeric indenyl, heterotrimeric indenyl, spirotrimeric indenyl, spiroisoquinolinyl, furyl, benzofuryl, isobenzofuryl, dibenzofuryl, thienyl, benzothienyl, isobenzothienyl, dibenzothienyl, pyrrolyl, isoindolyl, carbazolyl, indenocarbazolyl, pyridyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolinyl, benzo-6, 7-quinolinyl, benzo-7, 8-quinolinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthaloimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, thienyl, benzoxazolyl, naphthyridazolyl, anthraoxazolyl, phenanthroizolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, thienazolyl, thienyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthracenyl, 2, 7-diazapyrenyl, 2, 3-diazapyrenyl, 1, 6-diazapyrenyl, 1, 8-diazapyrenyl, 4,5,9, 10-tetrazolyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarboline, phenanthroline, 1,2, 3-triazolyl, 1,2, 4-triazolyl, benzotriazole, 1,2, 3-oxadiazolyl, 1,2, 4-oxadiazolyl, 1,2, 5-oxadiazolyl, 1,2, 3-thiadiazolyl, 1,2, 4-thiadiazolyl, 1,2, 5-thiadiazolyl, 1,3, 4-thiadiazolyl, 1,3, 5-triazinyl, 1,2, 4-triazinyl, 1,2, 3-triazinyl, tetrazolyl, 1,2,4, 5-tetrazinyl, 1,2,3, 4-tetrazinyl, 1,2,3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazolyl, or a combination of two or more thereof. But are not limited to these groups.
In the present invention, the "substituted or unsubstituted" group may be substituted with one substituent or may be substituted with a plurality of substituents, and when the number of substituents is plural, the substituents may be selected from different substituents, and the same meaning is given when the same expression mode is involved in the present invention, and the selection ranges of the substituents are not repeated as shown above.
In a preferred embodiment of the invention, each L 1、L2 is independently a single bond, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted phenylene group; preferably, each L 1、L2 is independently phenylene or a single bond; the substituents of each of the above substituted or unsubstituted groups are each independently selected from one or a combination of at least two of halogen, nitro, cyano, C6-C60 aryl, C3-C60 heteroaryl, C1-C20 straight or branched chain alkyl, C1-C10 alkoxy, C6-C30 aryloxy, amino, C1-C20 alkylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino.
In a preferred embodiment of the invention, R is selected from the group consisting of substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C1-C10 chain alkoxy, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C10 cycloalkoxy, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl; the substituents in each group are independently selected from one or more of halogen, carboxyl, nitro, cyano, amino, hydroxyl and sulfhydryl
In a preferred embodiment of the invention Ar 1 is one of a substituted or unsubstituted C10-C30 aryl, substituted or unsubstituted C10-C30 heteroaryl; r is a substituted or unsubstituted C1-C10 chain alkyl or a substituted or unsubstituted C6-C30 aryl; the substituents of each of the above substituted or unsubstituted groups are each independently selected from one or a combination of at least two of halogen, nitro, cyano, C6-C60 aryl, C3-C60 heteroaryl, C1-C20 straight or branched chain alkyl, C1-C10 alkoxy, C6-C30 aryloxy, amino, C1-C20 alkylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino.
In a preferred embodiment of the present invention, ar 2、Ar3 may be a substituted or unsubstituted group represented by the following formula:
Wherein the wavy line marks represent the connection positions of the groups; when Ar 2 has a substituent, it is preferable that the substituent is selected from the group consisting of sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, tert-pentyl, cyclopentyl, neopentyl; when Ar 3 has a substituent, it is preferred that the substituent is selected from one or a combination of at least two of halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;
in a preferred embodiment of the invention Ar 1 is a substituted or unsubstituted radical of the formula:
Ar 1 has a substituent selected from one or a combination of at least two of halogen, C1-C20 alkyl, C1-C20 alkoxy, C6-C60 aryl, and C3-C60 heteroaryl
In a preferred embodiment of the present invention, therefore, the formula (I) preferably has a structure represented by the following formulas (II) and (III),
In the formulae (II) to (VI), m, R, ar 1 and Ar 2 have the same meanings as those expressed in claim 1,
R a is selected from halogen, cyano, nitro, hydroxy, amino, C1-C20 alkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C60 aryl, C3-C60 heteroaryl; n is an integer from 0 to 6; more preferably, n is 0, m is 1, R is a C1-C6 chain alkyl group, preferably R is methyl or ethyl.
The inventors found that better device efficiency and lifetime can be obtained when Ar 3 is naphthyl, dibenzofuran, dimethylfluorenyl, and the specific reasons are not clear, and are presumed to be the following reasons: due to the introduction of the groups, molecules can be promoted to spread on the plane of the device, and the molecules of the light-emitting layer deposited afterwards are induced to also adopt such planar space stacking; the light-emitting molecules stacked in a planar spreading manner are beneficial to improving the light extraction efficiency, so that the current efficiency is improved; meanwhile, the space stacking of the molecular structure is enhanced, the compactness and the crystallinity are better, and the service life of the device is prolonged. From this point of view, ar 3 is more preferably naphthyl.
Specific examples of the compound represented by the formula (I) include any of the structures shown below, but are not limited to these specific compounds:
Another aspect of the present invention also provides an organic electroluminescent device comprising a first electrode, a second electrode, and one or more light-emitting functional layers interposed between the first electrode and the second electrode, wherein the light-emitting functional layers comprise the aryl-substituted amine compound of the present invention.
In another aspect, the present invention provides an electron blocking material for an organic electroluminescent device, which contains the compound described in the present invention.
Another aspect of the invention provides the use of a compound of the invention as a functional material in an organic electronic device comprising: organic electroluminescent devices, optical sensors, solar cells, lighting elements, organic thin film transistors, organic field effect transistors, organic thin film solar cells, information labels, electronic artificial skin sheets, sheet scanners, or electronic paper.
The invention also provides a display device which comprises the organic electroluminescent device.
In summary, the compound provided by the invention is favorable for obtaining higher luminous efficiency, excellent effect of low starting voltage and improvement of service life characteristic as an electron blocking material. 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 and is very suitable for industrial application.
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 and display manufacturing enterprises on high-performance materials.
The compound provided by the invention has higher hole affinity and hole transport property. The method can be used for electron blocking or hole injection in organic electronic devices (including but not limited to organic electroluminescent devices, optical sensors, solar cells, lighting elements, organic thin film transistors, organic field effect transistors, organic thin film solar cells, information labels, electronic artificial skin sheets, sheet type scanners or electronic papers).
The invention also provides an organic electroluminescent device comprising a first electrode, a second electrode and at least one or more light-emitting functional layers interposed between the first electrode and the second electrode, wherein the compound of the invention is used in at least one of the light-emitting functional layers.
The structure of the organic electroluminescent device is consistent with that of the existing device, for example, the organic electroluminescent device comprises an anode layer, a plurality of luminous functional layers and a cathode layer; the plurality of light-emitting functional layers include a light-emitting layer and at least one layer selected from an electron blocking layer, an electron transporting layer, and an electron injecting layer, wherein at least one layer selected from a hole transporting layer, a hole injecting layer, and an electron blocking layer contains the above-described organic compound of the present invention.
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 and display manufacturing enterprises on high-performance materials.
Detailed Description
The technical scheme of the invention is further more specifically described below. It will be apparent to those skilled in the art that the examples are merely to aid in understanding the invention and are not to be construed as a specific limitation thereof.
Method for obtaining the compounds of the invention
The representative synthetic routes for the compounds of formula (I) of the present invention are as follows:
Wherein Ar 1、Ar2、Ar3、L1、L2 and R, m have the same meaning as the symbols in the formula I; pd (PPh 3)4 represents tetrakis (triphenylphosphine palladium), pd 2(dba)3 represents tris (dibenzyl acetone) dipalladium (0), IPr.HCl represents 1, 3-bis (2, 6-diisopropylphenyl) imidazolyl chloride, naOBu-t represents sodium tert-butoxide, K 2CO3 represents potassium carbonate, (t-Bu) 3 P represents tri-tert-butylphosphine.
More specifically, the present invention provides, by way of example, a specific synthetic method for representative compounds, and solvents and reagents used in the following synthetic examples, all of which may be purchased or customized from the domestic chemical product market. In addition, the person skilled in the art can synthesize the compounds by known methods.
The organic electroluminescent device of the invention
The structure of the organic electroluminescent device of the present invention is a known structure, and the compound of the present invention is used for one or more of the electron blocking layers. The compounds of the present invention can also be used for host layers, hole transport layers, hole injection layers, according to the basic principle and usage habits. The organic electroluminescent device will be described in detail below.
In particular embodiments, a substrate may be used below the first electrode or above the second electrode. The substrates are all glass or polymer materials with excellent mechanical strength, thermal stability, water resistance and transparency. A Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode may be formed by sputtering or depositing a material serving as the first electrode on the substrate. When the first electrode is used as the anode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin dioxide (SnO 2), zinc oxide (ZnO), or the like, and any combination thereof may be used. When the first electrode is used as the cathode, metals or alloys such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), ytterbium (Yb), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), and any combinations thereof may be used.
The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compounds used as the organic material layer may be small organic molecules, large organic molecules and polymers, and combinations thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer hole transport layer containing only one compound and a single layer hole transport layer containing a plurality of compounds. The hole transport region may have a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL); wherein the HIL is located between the anode and the HTL and the EBL is located between the HTL and the light emitting layer.
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or conductive dopant containing polymers such as polystyrene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives such as the compounds shown below HT-1 to HT-51; or any combination thereof.
The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more of the compounds HT-1 through HT-51 described above, or one or more of the compounds HI-1-HI-3 described below; one or more compounds from HT-1 to HT-51 may also be used to dope one or more of HI-1-HI-3 described below.
The light emitting layer includes a light emitting dye (i.e., dopant) that can emit different wavelength spectrums, and may also include an electron blocking material (Host) at the same time. The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The plurality of monochromatic light emitting layers with different colors can be arranged in a plane according to the pixel pattern, or can be stacked together to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light emitting layer may be a single color light emitting layer capable of simultaneously emitting different colors such as red, green, and blue.
According to different technologies, the luminescent layer material can be made of different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescence luminescent material and the like. In an OLED device, a single light emitting technology may be used, or a combination of different light emitting technologies may be used. The different luminescent materials classified by the technology can emit light of the same color, and can also emit light of different colors.
In one aspect of the invention, the light-emitting layer employs fluorescence electroluminescence technology. The luminescent layer fluorescent electron blocking material thereof may be selected from, but is not limited to, one or more combinations of BFH-1 through BFH-17 listed below.
In one aspect of the invention, the light-emitting layer employs fluorescence electroluminescence technology. The luminescent layer fluorescent dopant thereof may be selected from, but is not limited to, one or more combinations of BFD-1 through BFD-24 listed below.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The electron blocking material of the light emitting layer is selected from one or more of PH-1 to PH-85.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The luminescent layer phosphorescent dopant thereof may be selected from, but is not limited to, one or more combinations of GPD-1 to GPD-47 listed below.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The luminescent layer phosphorescent dopant thereof may be selected from, but is not limited to, one or more combinations of the RPD-1 through RPD-28 listed below.
In one aspect of the invention, the light-emitting layer employs phosphorescent electroluminescence technology. The luminescent layer phosphorescent dopant may be selected from, but is not limited to, one or more combinations of YPD-1-YPD-11 listed below.
The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be an Electron Transport Layer (ETL) of a single layer structure including a single layer electron transport layer containing only one compound and a single layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
In one aspect of the invention, the electron transport layer material may be selected from, but is not limited to, combinations of one or more of ET-1 through ET-73 listed below.
In one aspect of the invention, a Hole Blocking Layer (HBL) is located between the electron transport layer and the light emitting layer. The hole blocking layer may employ, but is not limited to, one or more of the compounds ET-1 to ET-73 described above, or one or more of the compounds PH-1 to PH-46; mixtures of one or more compounds of ET-1 to ET-73 with one or more compounds of PH-1 to PH-46 may also be employed, but are not limited to.
The device may further include an electron injection layer between the electron transport layer and the cathode, the electron injection layer material including, but not limited to, a combination of one or more of the following:
LiQ、LiF、NaCl、CsF、Li2O、Cs2CO3、BaO、Na、Li、Ca、Mg、Yb。
Examples
The organic compound of the invention is representatively synthesized, and is applied to an organic electroluminescent device together with a corresponding comparative compound to test the device performance under the same conditions.
The present invention provides, by way of example, specific synthetic methods for representative compounds, such as solvents and reagents, intermediates, ethyl acetate, methanol, ethanol, and other chemical reagents used in the following synthesis examples, all of which may be purchased or customized from the domestic chemical product market.
Synthesis example 1: synthesis of Compound F1
Synthesis of F1-1
Synthesis of F1-1
In a 2000ml single-port bottle, 40.0g of M1, 52.17g of A, 2.68g of tetra (triphenylphosphine) palladium (namely Pd (PPH 3)4) and 64.18g of potassium carbonate (namely K 2CO3),900ml/300ml(Dioxane/H2 O) are added, the nitrogen is exchanged for 3 times in vacuum, the reaction is heated to 100 ℃ for 4 hours, the reaction is finished, the reaction is stopped, the reaction is cooled to room temperature, the organic phase is filtered by a silica gel column, the organic phase is concentrated, ethanol is added for refluxing and stirring for 2 hours, the yellow solid is obtained by cooling and suction filtration, and then 58g of pure product is obtained by recrystallisation twice by toluene/ethanol.
M/Z theory: 283; M/Z actual measurement: 283.
Synthesis of F1-2
Into a 1000ml single-port flask, 20.0g of F1-1, 19.28g of 1-bromo-9, 9-dimethylfluorene, 1.3g of tris (dibenzylideneacetone) dipalladium (i.e. Pd 2(dba)3), 1.2g of 1, 3-bis (2, 6-diisopropylphenyl) imidazolyl chloride (i.e. IPr.HCl), 13.5g of sodium tert-butoxide (i.e. NaOBu-t), 600ml of toluene, vacuum-pumping and nitrogen-exchanging are added for 3 times, and the reaction is heated to 90 ℃ for 12 hours. After the reaction, the reaction was stopped and cooled to room temperature. The organic phase is filtered by a silica gel column, concentrated, added with ethanol, refluxed and stirred for 2 hours, cooled and filtered to obtain yellow solid, and then recrystallized twice by toluene/ethanol to obtain 21.5g of pure product.
M/Z theory: 475(s); M/Z actual measurement: 475.
Synthesis of F1
In a 1000ml single port flask, 20.0g of F1-2, 7.2g of bromobenzene, 0.3g of tris (dibenzylideneacetone) dipalladium (i.e., pd 2(dba)3), 0.3ml of tri-tert-butylphosphine (i.e., t-Bu) 3 P), 8.9g of sodium tert-butoxide (i.e., naOBu-t), 600ml of toluene, vacuum-pumping and nitrogen-exchanging for 3 times, and the reaction temperature was raised to 110℃for 12 hours. After the reaction, the reaction was stopped and cooled to room temperature. The organic phase is filtered by a silica gel column, concentrated, added with ethanol, refluxed and stirred for 2 hours, cooled and filtered to obtain yellow powder, and then recrystallized twice by toluene/ethanol to obtain 16.5g of pure product.
M/Z theory: 551; M/Z actual measurement: 551.
Synthesis example 2 Synthesis example 10
The synthesis of the compounds was carried out based on the same procedure as in the synthesis example, wherein the important raw materials were replaced according to the following table 1:
Table 1 summary of synthesis example raw materials and products
Device embodiment
The preparation process of the organic electroluminescent device in this embodiment is as follows:
The glass plate coated with the ITO transparent conductive layer was sonicated in commercial cleaners, rinsed in deionized water, and rinsed in acetone: ultrasonic degreasing in ethanol mixed solvent, baking in clean environment to completely remove water, cleaning with ultraviolet light and ozone, and bombarding the surface with low-energy cation beam;
Placing the glass substrate with the anode in a vacuum cavity, vacuumizing to < 1X 10 -5 Pa, vacuum thermal evaporating 10nm of HT-4:HI-3 (97/3,w/w) mixture as a hole injection layer, 60nm of compound HT-4 as a hole transmission layer, 60nm of compound F1 as an electron blocking layer, 40nm of compound PH-34:RPD-8 (97/3,w/w) binary mixture as a light emitting layer, 25nm of compound ET-46:ET-57 (50/50, w/w) mixture as an electron transmission layer, 0.5nm of LiF as an electron injection layer and 150nm of metallic aluminum as a cathode on the anode layer. The total evaporation rate of all organic layers and LiF was controlled at 0.1 nm/sec, and the evaporation rate of the metal electrode was controlled at 1 nm/sec.
Device examples 2-10 were fabricated in the same manner as 1, except that F1 in the electron blocking layer was replaced with F2, 28, F48, F172, F186, F201, F320, F376, F421, respectively.
Devices of comparative examples 1 to 4 were fabricated in the same manner as in device example 1, except that F1 in the electron blocking layer was replaced with P1 (see CN 110511151A), P2 (see US 20210376241A), P3 (see CN 110950762A), and P4 (see CN 112979478A), respectively:
Method for testing a device (including apparatus and test conditions):
The organic electroluminescent device prepared by the above procedure was subjected to the following performance measurement:
The driving voltage and current efficiency of the organic electroluminescent devices prepared in examples 1 to 10 and comparative examples 1 to 4 were measured using a digital source meter and a luminance meter at the same luminance. Specifically, the voltage was increased at a rate of 0.1V per second, and the driving voltage, which is the voltage when the luminance of the organic electroluminescent device reached 3000cd/m 2, was measured, while the current density at that time was measured; the ratio of brightness to current density is the current efficiency; the LT98 lifetime of comparative example 1 was set to 1, and the LT98 lifetime of the other compounds were all relative to that of comparative example 1.
The results are summarized in table 2.
TABLE 2
The results show that when the novel organic material is used for an organic electroluminescent device and the brightness of the device is 3000cd/m 2, the current efficiency can reach more than 20cd/A, and compared with comparative example 1, LT98 can reach more than 1.7 times, so that the novel organic material can effectively improve the current efficiency, prolong the service life of the device and is a red light electron blocking layer material with good performance.
The experimental data show that the novel organic material provided by the invention is used as an electron blocking material of an organic electroluminescent device, is an organic luminescent functional material with good performance, and has a wide application prospect.
The applicant states that the detailed method of the present invention is illustrated by the above examples, but the present invention is not limited to the detailed method described above, i.e. it does not mean that the present invention must be practiced in dependence upon the detailed method described above. It should be apparent to those skilled in the art that any modification of the present invention, equivalent substitution of raw materials for the product of the present invention, addition of auxiliary components, selection of specific modes, etc., falls within the scope of the present invention and the scope of disclosure.
Claims (13)
1. An aryl-substituted amine compound characterized by being a compound having a structure represented by the formula (I):
Ar 1 is one of a substituted or unsubstituted C8-C60 aryl group, a substituted or unsubstituted C8-C60 heteroaryl group in formula (I);
L 1、L2 is independently selected from one of single bond, substituted or unsubstituted C6-C30 arylene, and substituted or unsubstituted C3-C30 heteroarylene;
Ar 2、Ar3 is independently selected from one of substituted or unsubstituted C6-C60 aryl and substituted or unsubstituted C3-C60 heteroaryl;
R is selected from halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C2-C8 alkenyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; m is an integer from 1 to 6, and at least one R is methyl; each R is the same or different and R is optionally fused to or not to an adjacent group, preferably R is not fused to an adjacent group;
The substituents in each of the above substituted or unsubstituted groups are each independently selected from one or a combination of at least two of halogen, C1-C20 straight or branched chain alkyl, C3-C20 cycloalkyl, C3-C20 heterocycloalkyl, C1-C10 alkoxy, carboxyl, nitro, cyano, amino, hydroxyl, mercapto, C1-C20 alkylsilyl, C1-C20 alkylamino, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryloxy, C3-C30 heteroaryloxy, C6-C60 aryl or C3-C60 heteroaryl;
The expression "ring structure" indicates that the linking site is located at any position on the ring structure that is capable of bonding.
2. The aryl substituted amine compound according to claim 1, wherein,
Each L 1、L2 is independently a single bond, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted phenylene group; preferably, each L 1、L2 is independently phenylene or a single bond;
The substituent groups of the above-mentioned substituted or unsubstituted groups are each independently selected from one or a combination of at least two of halogen, nitro, cyano, C6-C60 aryl, C3-C60 heteroaryl, C1-C20 straight or branched alkyl, C1-C10 alkoxy, C6-C30 aryloxy, amino, C1-C20 alkylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino.
3. The aryl substituted amine compound according to claim 1 or 2, wherein,
R is selected from the group consisting of substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C1-C10 chain alkoxy, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C3-C10 cycloalkoxy, substituted or unsubstituted C6-C30 aryl, and substituted or unsubstituted C3-C30 heteroaryl;
the substituents in the above-mentioned substituted or unsubstituted groups are each independently selected from one or a combination of at least two of halogen, carboxyl, nitro, cyano, amino, hydroxyl and mercapto.
4. The aryl-substituted amine compound according to any one of claim 1 to 3,
Ar 1 is a substituent or one of unsubstituted C10-C30 aryl, substituted or unsubstituted C10-C30 heteroaryl;
R is a substituted or unsubstituted C1-C10 chain alkyl or a substituted or unsubstituted C6-C30 aryl;
The substituent groups of the above-mentioned substituted or unsubstituted groups are each independently selected from one or a combination of at least two of halogen, nitro, cyano, C6-C60 aryl, C3-C60 heteroaryl, C1-C20 straight or branched alkyl, C1-C10 alkoxy, C6-C30 aryloxy, amino, C1-C20 alkylsilyl, C6-C30 arylamino, C3-C30 heteroarylamino.
5. The aryl substituted amine compound according to claim 1, wherein,
Ar 2 and Ar 3 are each independently substituted or unsubstituted, the following groups:
wherein the wavy line marks represent the connection positions of the groups;
Ar 2 has a substituent selected from sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, tert-pentyl, cyclopentyl and neopentyl; ar 3 has a substituent selected from one or a combination of at least two of halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 aryl, and substituted or unsubstituted C3-C60 heteroaryl.
6. The aryl-substituted amine compound according to any one of claims 1 to 5, wherein,
Ar 1 is a substituted or unsubstituted group of:
Ar 1 has a substituent selected from one or a combination of at least two of halogen, C1-C20 alkyl, C1-C20 alkoxy, C6-C60 aryl and C3-C60 heteroaryl.
7. The aryl-substituted amine compound according to claim 1, wherein the compound has any one of the structures represented by the following formulas (II) to (VI),
In the formulae (II) to (VI), m, R, ar 1 and Ar 2 have the same meaning as expressed in claim 1;
R a is selected from halogen, cyano, nitro, hydroxy, amino, C1-C20 alkyl, C1-C20 alkoxy, C1-C20 silyl, C6-C60 aryl, C3-C60 heteroaryl; n is an integer from 0 to 6;
preferably, n is 0, m is 1, R is a C1-C6 chain alkyl group, preferably R is methyl or ethyl.
8. The aryl substituted amine compound according to claim 1, wherein said formula (I) has any one of the structures shown below:
9. An organic electroluminescent device comprising a first electrode, a second electrode, and one or more light-emitting functional layers interposed between the first electrode and the second electrode, wherein the light-emitting functional layer comprises the aryl-substituted amine compound according to any one of claims 1 to 8.
10. An electron blocking material for an organic electroluminescent device, comprising the aryl-substituted amine compound according to any one of claims 1 to 8.
11. Use of an aryl substituted amine compound according to any one of claims 1 to 8 as a functional material in an organic electronic device comprising: organic electroluminescent devices, optical sensors, solar cells, lighting elements, organic thin film transistors, organic field effect transistors, organic thin film solar cells, information labels, electronic artificial skin sheets, sheet scanners, or electronic paper.
12. The use according to claim 11 as an electron blocking layer material, a hole injection layer material, or a hole transport layer material.
13. A display device comprising the organic electroluminescent device according to claim 9.
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| Publication Number | Publication Date |
|---|---|
| CN118271187A true CN118271187A (en) | 2024-07-02 |
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