CN118271188A - Aromatic amine type organic compound, application thereof and organic electroluminescent device - Google Patents
Aromatic amine type organic compound, application thereof and organic electroluminescent deviceInfo
- Publication number
- CN118271188A CN118271188A CN202211743322.6A CN202211743322A CN118271188A CN 118271188 A CN118271188 A CN 118271188A CN 202211743322 A CN202211743322 A CN 202211743322A CN 118271188 A CN118271188 A CN 118271188A
- Authority
- CN
- China
- Prior art keywords
- substituted
- unsubstituted
- group
- ring
- 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
- 150000002894 organic compounds Chemical class 0.000 title claims description 25
- 150000004982 aromatic amines Chemical class 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 78
- 239000000463 material Substances 0.000 claims abstract description 60
- 125000003118 aryl group Chemical group 0.000 claims abstract description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 10
- -1 cyano, nitro, hydroxy, amino Chemical group 0.000 claims description 172
- 239000010410 layer Substances 0.000 claims description 105
- 125000001072 heteroaryl group Chemical group 0.000 claims description 41
- 230000000903 blocking effect Effects 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 26
- 125000000217 alkyl group Chemical group 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 18
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052805 deuterium Inorganic materials 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000001769 aryl amino group Chemical group 0.000 claims description 7
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 6
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
- 238000006467 substitution reaction Methods 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 5
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 4
- 239000010409 thin film Substances 0.000 claims description 4
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 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 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- 125000005549 heteroarylene group Chemical group 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000005023 xylyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 239000002346 layers by function Substances 0.000 claims 3
- 230000003287 optical effect Effects 0.000 claims 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 abstract description 11
- 230000005525 hole transport Effects 0.000 description 21
- 238000002347 injection Methods 0.000 description 18
- 239000007924 injection Substances 0.000 description 18
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- 230000000052 comparative effect Effects 0.000 description 13
- 238000005516 engineering process Methods 0.000 description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 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 9
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 9
- 238000005401 electroluminescence Methods 0.000 description 9
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 9
- 125000001624 naphthyl group Chemical group 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000011368 organic material Substances 0.000 description 8
- 125000001725 pyrenyl group Chemical group 0.000 description 8
- 125000004429 atom Chemical group 0.000 description 7
- 235000010290 biphenyl Nutrition 0.000 description 7
- 239000004305 biphenyl Substances 0.000 description 7
- 239000002019 doping agent Substances 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 239000010408 film Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 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
- 239000000758 substrate Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 125000001544 thienyl group Chemical group 0.000 description 6
- 101100273664 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) ccp-1 gene Proteins 0.000 description 5
- 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 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 230000003111 delayed effect Effects 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 125000005561 phenanthryl group Chemical group 0.000 description 5
- 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 4
- 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 4
- 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
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 4
- 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 4
- 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 4
- 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 4
- 239000011575 calcium Substances 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 4
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 4
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 4
- 125000002541 furyl group Chemical group 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 125000001041 indolyl group Chemical group 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal 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
- 239000001301 oxygen Substances 0.000 description 4
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 4
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 4
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 125000000168 pyrrolyl group Chemical group 0.000 description 4
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 4
- ZHQNDEHZACHHTA-UHFFFAOYSA-N 9,9-dimethylfluorene Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 ZHQNDEHZACHHTA-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 2
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-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
- AVJBQMXODCVJCJ-UHFFFAOYSA-M 1,3-bis[2,6-di(propan-2-yl)phenyl]imidazol-1-ium;chloride Chemical compound [Cl-].CC(C)C1=CC=CC(C(C)C)=C1N1C=[N+](C=2C(=CC=CC=2C(C)C)C(C)C)C=C1 AVJBQMXODCVJCJ-UHFFFAOYSA-M 0.000 description 2
- JENANTGGBLOTIB-UHFFFAOYSA-N 1,5-diphenylpentan-3-one Chemical compound C=1C=CC=CC=1CCC(=O)CCC1=CC=CC=C1 JENANTGGBLOTIB-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- 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
- BGEVROQFKHXUQA-UHFFFAOYSA-N 71012-25-4 Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=C1C1=CC=CC=C1N2 BGEVROQFKHXUQA-UHFFFAOYSA-N 0.000 description 2
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 2
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical compound C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 description 2
- JTPHKHUWLNQSSU-UHFFFAOYSA-N C1=CC=CC=2C=CC=3C=4C=CC=CC4NC3C21.C2(=CC=CC1=CC=CC=C21)N2C1=CC=CC=C1C=1C=CC=CC21 Chemical compound C1=CC=CC=2C=CC=3C=4C=CC=CC4NC3C21.C2(=CC=CC1=CC=CC=C21)N2C1=CC=CC=C1C=1C=CC=CC21 JTPHKHUWLNQSSU-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 229940008309 acetone / ethanol Drugs 0.000 description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
- 230000003213 activating effect Effects 0.000 description 2
- 125000000304 alkynyl group Chemical group 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 group C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
- 239000012964 benzotriazole Chemical group 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
- 125000006267 biphenyl group Chemical group 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000005238 degreasing Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 2
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000011010 flushing procedure Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 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
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 2
- 229960005544 indolocarbazole Drugs 0.000 description 2
- 125000005990 isobenzothienyl group Chemical group 0.000 description 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 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
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-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
- 238000011056 performance test Methods 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
- 239000000843 powder Substances 0.000 description 2
- 230000008569 process Effects 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
- 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
- 239000012925 reference material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000011593 sulfur 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
- 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
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 2
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- 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
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Abstract
The invention provides an aromatic amine type organic functional compound and application thereof, wherein the aromatic amine type organic functional compound has a structure shown as a formula (I): the AR group is an aromatic ring, and the A group is deuterated methyl substituted fluorene ring; the invention also provides application of the compound as a functional material of an organic electroluminescent device.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to a composition for an organic electroluminescence device and the organic electroluminescence device.
Background
The organic electroluminescent (Organic Light Emission Diodes, OLED) device is an emerging display technology in recent years, has the characteristics of high brightness, quick response, low energy consumption, wide viewing angle, flexibility, wide temperature application range, simple process and the like, is widely applied to display panels of products such as lighting fixtures, smart phones, tablet computers and the like, and further expands the application fields of large-size display products such as televisions and the like.
The OLED device has a sandwich-like structure and comprises a positive electrode, a negative electrode and an organic functional material layer sandwiched between the positive electrode and the negative electrode; when a voltage is applied to an electrode of the OLED device, electrons and holes are injected, transported to a light emitting region, and recombined therein, respectively, thereby generating excitons and emitting light. The core of the OLED device is an organic functional material layer, and common organic functional materials constituting the material layer include: 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.
Common fluorescent emitters emit light mainly using singlet excitons generated when electrons and holes are combined, and are still widely used in various OLED products. Some metal complexes (e.g., iridium complexes) can emit light using both triplet and singlet excitons, known as phosphorescent emitters, and can have energy conversion efficiencies up to four times greater than conventional fluorescent emitters. The thermal excitation delayed fluorescence (TADF) technique can achieve higher luminous efficiency by promoting transition from triplet excitons to singlet excitons, and still effectively utilizing triplet excitons without using a metal complex. The thermal excitation sensitized fluorescence (TASF) technology adopts a material with TADF property, and sensitizes the luminophor in an energy transfer mode, so that higher luminous efficiency can be realized.
On one hand, the hole transport material needs to have proper HOMO energy level and proper energy gap between the hole transport material and the anode, so that the injection of holes is facilitated, and the reduction of working voltage can be facilitated; on the other hand, the hole transport material regulates and controls the transport balance of carriers in the device, and improves the carrier mobility of the hole transport material, so that the luminous efficiency is improved, and the attenuation of the device is delayed. Although products using OLED display technology are commercialized at present, there are further improved requirements on efficiency, service life, and the like of devices. Therefore, there is a need in the art to develop more kinds of organic materials with higher performance to improve the performance of the organic electroluminescent device, so that the device has higher luminous efficiency and lower driving voltage.
Disclosure of Invention
The field is urgent to develop organic electroluminescent materials capable of improving luminous efficiency of devices, reducing driving voltage and prolonging service life. The electron blocking material is used as an important light-emitting auxiliary material, and can effectively improve the injection and transmission of holes and exciton blocking performance, so that the device performance is directly influenced, and therefore, the electron blocking material is focused by people. It is therefore an object of the present application to provide an organic compound and use thereof, which is applied to an organic electroluminescent device, is particularly suitable as an electron blocking layer material and/or a hole transport layer material, can improve and balance the transport of carriers in the device, reduce the capacitance of the device, improve the luminous efficiency and prolong the service life.
As a result of intensive studies, the inventors have found that a compound having a structure represented by the formula (I) can achieve the object of the present invention, and specifically, the present invention provides a compound of the following formula (I),
Wherein ring AR is selected from substituted or unsubstituted C7-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl, A is a group of formula (a), wherein X is a single bond, O, S, NR 11 or CR 12R13; in formula (a), CD 3 represents deuterated methyl;
ar 1、Ar2 is independently one of a substituted or unsubstituted C6-C60 aryl, a substituted or unsubstituted C3-C60 heteroaryl; provided that the Ar 2 substituted position is ortho to the N atom substituted position,
R 11、R12、R13 is each independently hydrogen, deuterium, halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, R 12 and R 13 are linked to form a ring, or are not linked to form a ring,
N is each independently an integer from 1 to 4, each R 4 is the same or different and is each independently selected from hydrogen, deuterium, halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, adjacent R 4 being linked to form a ring or not linked to form a ring;
L 1、L2 is independently a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group;
The substituted substituents are each independently selected from at least one of halogen, C1-C20 straight or branched 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; wherein the substituents of L 1 and Ar 1 are not perdeuterated alkyl groups;
The expression "represents a linking site" and "a" drawn ring structure indicates any position on the ring structure where a linking site can form a bond.
The specific reasons for the excellent properties of the compounds of the present invention are not clear, and it is presumed that the following reasons are possible: firstly, the triarylamine compound has good hole carrier transport capacity; when the ring AR is a larger aromatic group, the overall LUMO energy level of the compound is shallower, the exciton is prevented from diffusing to the hole layer, the efficiency is improved, and the service life is prolonged; CD 3 of a specific site in the formula (a) of the compound has heavier deuterium atoms relative to hydrogen atoms, better stability and better blocking effect on excitons, which is beneficial to prolonging the service life of the device; the Ar 2 substitution position is very important to be positioned at the ortho position of the N atom substitution position and positioned at the ortho position of the amino N atom, so that the torsion degree of the molecule can be effectively regulated and controlled to reduce the crystallinity of the molecule; the specific groups are matched with each other, so that the stacking density of molecules can be effectively regulated and controlled, the LUMO and HOMO energy levels are optimized, the refractive property of the molecules is improved, and the excitons are effectively prevented from diffusing to a hole layer, so that the organic electroluminescent material with better space structure and better film stacking form is obtained, the organic electroluminescent material is particularly suitable for an electron blocking layer and/or a hole transport layer, the luminous efficiency of a device is improved, the service life of the device is prolonged, and the comprehensive performance of the device is improved.
It should be noted that unless otherwise defined below, all technical and scientific terms used herein are intended to have the same meaning as commonly understood by one of ordinary skill in the art. References to techniques used herein are intended to refer to techniques commonly understood in the art, including variations of those that are obvious to those skilled in the art or alternatives to equivalent techniques. While the following terms are believed to be well understood by those skilled in the art, the following definitions are set forth to better explain the present invention.
In the present specification, the expression of Ca to Cb and Ca to Cb means that the group has a carbon number of a to b, and unless otherwise specified, the carbon number generally excludes the carbon number of a substituent. When C1-30 is described, it includes but is not limited to C1, C2, C3, C4, C3, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C22, C24, C26, C28, etc., and other numerical ranges are not repeated.
The terms "comprising," "including," "having," "containing," or "involving," and other variations thereof herein, are inclusive (inclusive) or open-ended and do not exclude additional unrecited elements or method steps.
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.
Heteroatoms in the present invention are generally selected from N, O, S, P, si and Se, preferably from N, O, S.
As used herein, the terms "heterocyclyl" and "heterocycle" refer to a saturated (i.e., heterocycloalkyl) or partially unsaturated (i.e., having one or more double and/or triple bonds within the ring) cyclic group having at least one ring atom that is a heteroatom selected from N, O and S, and the remaining ring atoms that are C.
As used herein, the terms "(arylene) and" aromatic ring "refer to an all-carbon monocyclic or fused-ring polycyclic aromatic group having a conjugated pi-electron system. As used herein, the terms "(arylene) heteroaryl" and "heteroaryl ring" refer to a monocyclic, bicyclic, or tricyclic aromatic ring system. As used herein, the term "aralkyl" preferably denotes aryl or heteroaryl substituted alkyl, wherein the aryl, heteroaryl and alkyl are as defined herein.
As used herein, the term "halo" or "halogen" group is defined to include F, cl, br or I.
The term "substitution" means that one or more (e.g., one, two, three, or four) hydrogens on the designated atom are replaced with a selection from the indicated group, provided that the designated atom's normal valency is not exceeded, and that the substitution forms a stable compound. Combinations of substituents and/or variables are permissible only if such combinations result in stable compounds.
If substituents are described as "independently selected from" a group, each substituent is selected independently of the other. Thus, each substituent may be the same as or different from another (other) substituent.
The term "one or more" as used herein means 1 or more than 1, such as 2, 3, 4, 5 or 10, under reasonable conditions.
As used herein, unless indicated, the point of attachment of a substituent may be from any suitable position of the substituent.
When the bond of a substituent is shown as a bond through the ring connecting two atoms, then such substituent may be bonded to any ring-forming atom in the substitutable ring.
The term "about" means within + -10%, preferably within + -5%, more preferably within + -2% of the stated value.
In the structural formulae disclosed in the present specification, if not specified,And "+" is a linking site, and the expression of the "-" scored ring structure indicates that the linking site is at any position on the ring structure that is capable of bonding.
The above-mentioned C6 to C60 aromatic ring and C3 to C60 heteroaromatic ring in the present invention are aromatic groups satisfying pi conjugated system, and include both cases of monocyclic residues and condensed ring residues unless otherwise specified. By monocyclic residue 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 residues refer to molecules containing at least two benzene rings, but the benzene rings are not independent of each other, but share the ring edges to be condensed with each other, such as naphthyl, anthryl, phenanthryl 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.; fused 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, illustratively, quinoline, isoquinoline, benzofuran, dibenzofuran, benzothiophene, dibenzothiophene, and the like.
In the present specification, the substituted or unsubstituted C6 to C60 aromatic ring is preferably a C6 to C30 aromatic ring, more preferably an aromatic ring in the group consisting of phenyl, naphthyl, anthryl, benzanthrenyl, phenanthryl, benzophenanthryl, pyrenyl, hole, perylene, fluoranthenyl, naphthacene, pentacenyl, benzopyrene, biphenyl, terphenyl, tetrabiphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthryl, dihydropyrenyl, tetrahydropyrenyl, cis or trans indenofluorenyl, trimeric indenyl, heterotrimeric indenyl, spirotrimeric indenyl, spiroheterotrimeric indenyl. Specifically, the biphenyl group is selected from the group consisting of 2-biphenyl group, 3-biphenyl group and 4-biphenyl group; terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl comprises 1-naphthyl or 2-naphthyl; the anthracenyl is selected from the group consisting of 1-anthracenyl, 2-anthracenyl and 9-anthracenyl; the fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; and the tetracenyl is selected from the group consisting of 1-tetracenyl, 2-tetracenyl and 9-tetracenyl. Preferred examples of the aromatic ring 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. In the present invention, the C10-C60 aryl group means an example of a group in which the number of C in the aryl group is 10 or more.
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.
In the present specification, the substituted or unsubstituted C3 to C60 heteroaryl ring is preferably a C3 to C30 heteroaryl ring, and may be a nitrogen-containing heteroaryl group, an oxygen-containing heteroaryl group, a sulfur-containing heteroaryl group, or the like, and specific examples thereof include: from furyl, thienyl, pyrrolyl, pyridyl, benzofuryl, benzothienyl, isobenzofuryl, isobenzothienyl, indolyl, isoindolyl, dibenzofuryl, dibenzothienyl, carbazolyl and derivatives thereof, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolinyl, benzo-6, 7-quinolinyl, benzo-7, 8-quinolinyl, phenothiazinyl, phenazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalinoimidazolyl, thienyl, benzoxazolyl, naphthazolyl, anthracenooxazolyl, phenanthroazolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzopyridazinyl, pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazaanthracenyl, 7, 3, 4-dipyrene, 4, 5-dipyrene, 1, 5-diazapyrenyl, 4-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, heteroaromatic rings formed by 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 heteroaromatic ring in the present invention, for example, a heteroaromatic ring of furyl, thienyl, pyrrolyl, benzofuryl, benzothienyl, isobenzofuryl, indolyl, dibenzofuryl, dibenzothienyl, carbazolyl and derivatives thereof, wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole benzocarbazole, dibenzocarbazole or indolocarbazole.
In the present specification, the substituted or unsubstituted C3 to C60 heteroaryl group is preferably a C3 to C30 heteroaryl group, 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.
As the aryl ether group and heteroaryl ether group in the present invention, the above-mentioned aryl group, heteroaryl group and oxygen group can be mentioned. Examples of the arylamino group and the heteroarylamino group in the present invention include those obtained by substituting one or two H groups in the above-mentioned aryl group and heteroaryl group with-NH 2 group.
In the present specification, a chain alkyl group also includes a concept of a straight chain as well as a branched alkyl group. Examples of the C1-C20 alkyl group include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, 2-methylbutyl, n-pentyl, sec-pentyl, neopentyl, n-hexylneohexyl, n-heptyl, n-octyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2-trifluoroethyl and the like.
In the present specification, the C3-C20 cycloalkyl group includes a monocycloalkyl group and a polycycloalkyl group, and as specific examples, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, and the like can be exemplified.
The number of carbon atoms of the C2-C20 linear or cyclic alkenyl group is preferably 2 to 10. Specific examples thereof include vinyl, 1-propenyl, 2-butenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 5-hexenyl, 7-octenyl, and groups in which these groups have substituents such as alkyl groups and alkoxy groups.
The number of carbon atoms of the C2-C20 linear or cyclic alkynyl group is preferably 2 to 10. Specific examples of the alkynyl group include an ethynyl group, a 1-propynyl group, a 2-butynyl group, a 3-pentynyl group, a 4-pentynyl group, a 1-hexynyl group, a 5-hexynyl group, and groups in which these groups have substituents such as an alkyl group and an alkoxy group.
In the present specification, the term "alkoxy" refers to a group composed of the aforementioned chain alkyl group and oxygen, or a group composed of the aforementioned cycloalkyl group and oxygen.
Examples of the C1-C20 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-C20 silyl group include silyl groups substituted with the groups exemplified in the above-mentioned C1-C20 alkyl groups, that is, groups formed by substituting one, two or three hydrogens on the silyl groups with the above-mentioned chain alkyl groups or cycloalkyl groups. Specific examples include: and methylsilyl, dimethylsilyl, trimethylsilyl, ethylsilyl, diethylsilyl, triethylsilyl, t-butyldimethylsilyl, t-butyldiphenylsilyl, and the like.
In a preferred embodiment of the invention, each L 1、L2 is independently one of a substituted or unsubstituted C6-C24 arylene, a substituent or an unsubstituted C3-C24 heteroarylene; the following substituted or unsubstituted structures are preferred:
the substituted substituents are each independently selected from at least one 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, and the expression of the "-" is a linking site, and the expression of the "-" scratched ring structure indicates any position on the ring structure that can form a bond.
Further preferably, each L 1 or L 2 is independently a group;
In a preferred embodiment of the invention, the ring AR is a C7-C12 aryl,
Preferably ring AR is one of the following groups:
in a preferred embodiment of the present invention, the organic compound of formula (I) may be represented by structures represented by formulas (II) - (IV);
Wherein A, ar 1、Ar2、L1、L2 is as defined in formula (I),
R 1 is selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, or R 1 is linked to the other C atoms of the benzene ring to which it is attached to form a ring structure;
R 1 is more preferably hydrogen.
In a preferred embodiment of the invention, ar 1 is selected from the following groups, substituted or unsubstituted:
Wherein ". Smallcap" is a linking site, and each of A1 to A3 is independently one of a substituted or unsubstituted C1 to C30 chain alkyl, C3 to C20 cycloalkyl, C6 to C20 aryl, C5 to C20 heteroaryl, or a combination of at least two thereof;
When the above groups have substituents, the substituents are selected from one or a combination of at least two of C1-C12 chain alkyl, C3-C12 cycloalkyl, C2-C10 alkenyl, C1-C10 alkoxy or thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl, and C3-C30 heteroaryl; further preferred substituents are methyl, tert-butyl, tert-amyl, cyclohexane, adamantyl, phenyl, tolyl, xylyl.
In a preferred embodiment of the invention Ar 2 is independently a C10-C30 aryl group substituted or unsubstituted by R ', a C3-C30 heteroaryl group substituted or unsubstituted by R'; r' is a C1-C10 straight or branched alkyl group, a C3-C12 cycloalkyl group, a C2-C10 alkenyl group, a C6-C10 aryl group, a C3-C10 heteroaryl group,
Further preferably, ar 2 is the following group:
still more preferably Ar 2 is the following group:
In a preferred embodiment of the invention, X is a single bond, O, CR 22R23;R22、R23 are each independently H, methyl, phenyl, or R 22、R23 are linked to form a cyclohexane ring, a cyclopentane ring, a dibenzocyclopentane ring; n is 0, and L 1 and L 2 are each independently a single bond, naphthylene or phenylene.
As specific compounds of the present invention, any one having the structure shown below is preferable, however, not limited to these compounds:
It is a further object of the present invention to provide the use of a compound according to one of the objects. The compound of the invention can be applied to not only organic electroluminescent devices, but also other types of organic electronic devices, including organic field effect transistors, organic thin film solar cells, information tags, electronic artificial skin sheets, sheet scanners or electronic papers. Preferably, the compound acts as an electron blocking layer material in the organic electroluminescent device.
It is a further object of the present invention to provide an organic electroluminescent device comprising a first electrode, a second electrode and at least one organic layer interposed between the first electrode and the second electrode, wherein the organic layer contains at least one compound according to one of the objects.
Preferably, the organic layer comprises an electron blocking layer containing at least one compound of one of the purposes.
Compared with the prior art, the invention has the advantages that:
Through the design of the molecular structure, the aromatic amine N is connected with the ortho position of the aryl or heteroaryl, which is favorable for improving mobility, so that the injection and migration of holes are well balanced, the molecular space structure is more compact, the film stacking form is good, and the stability and the film forming property are good. N is connected with Compared with the compound containing H atoms, the structural unit has better thermodynamic stability and higher tolerance to electrons, and can effectively prolong the service life of the device.
The preparation process of the compound is simple and feasible, raw materials are easy to obtain, and the compound is suitable for mass production and amplification. The experimental data show that the novel organic material is used as an electron blocking material of an organic electroluminescent device, is obviously improved compared with the prior art, is an organic luminescent functional material with good performance, and has wide application prospect.
Because the electron blocking material has similar requirements on material performance as hole injection materials and hole transport materials. The compounds of the invention can therefore also be used for hole injection materials, hole transport materials.
It should be noted that the possible actions of the individual groups/features are described separately in the present application for convenience of explanation, but this does not mean that the groups/features are acting in isolation. In fact, the reason for obtaining good properties is essentially an optimal combination of the whole molecule, as a result of the synergy between the individual groups, rather than the effect of a single group.
Drawings
FIG. 1 is a graph comparing the thermal stability of a compound of the invention and a comparative compound.
Detailed Description
The technical scheme of the invention is further described by the following specific embodiments. 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.
General synthetic method of compound
The compounds of the present application can be synthesized by known methods. For example, a representative synthetic route of the organic compound having the structure represented by formula (I) in the present application is as follows:
in the present application, a representative synthetic route of the organic compound having the structure shown in formula I is as follows:
Wherein each symbol has the same meaning as in formula I; pd 2(dba)3 represents tris (dibenzyl acetone) dipalladium (0), IPr.HCl represents 1, 3-bis (2, 6-diisopropylphenyl) imidazolium chloride, t-Buona represents sodium tert-butoxide, and (t-Bu) 3 P represents tri-tert-butylphosphine.
The preparation of the organic compound according to the present application includes, but is not limited to, the above-mentioned methods, and the organic compound of formula I synthesized by a person skilled in the art using other methods is also included in the scope of the present application.
More specifically, the present application provides, by way of example, a specific synthetic method for the organic compound, and the solvents and reagents used in the following synthetic examples, all of which can be purchased or customized from the chemical product market. In addition, the person skilled in the art can synthesize by other known methods.
Embodiments of the device of the invention
The organic electroluminescent device (OLED) according to the present invention is characterized by containing the compound according to the present invention as a functional material. It is known that an OLED comprises a first electrode and a second electrode, and an organic material layer between the electrodes. The organic material may in turn be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
In particular embodiments, a substrate may be used below the first electrode or above the second electrode. The substrates are all glass or polymer materials with excellent mechanical strength, thermal stability, water resistance and transparency. A Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode may be formed by sputtering or depositing a material serving as the first electrode on the substrate. When the first electrode is used as the anode, 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 luminescent layer comprises luminescent dyes (i.e. dopants) that can emit different wavelength spectra, and may also comprise Host materials (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The plurality of monochromatic light emitting layers with different colors can be arranged in a plane according to the pixel pattern, or can be stacked together to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light emitting layer may be a single color light emitting layer capable of simultaneously emitting different colors such as red, green, and blue.
According to different technologies, the luminescent layer material can be made of different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescence luminescent material and the like. In an OLED device, a single light emitting technology may be used, or a combination of different light emitting technologies may be used. The different luminescent materials classified by the technology can emit light of the same color, and can also emit light of different colors.
In one aspect of the invention, the light-emitting layer employs fluorescence electroluminescence technology. The luminescent layer fluorescent host material thereof may be selected from, but is not limited to, one or more combinations of BFH-1 to 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 light-emitting layer host material is selected from, but not limited to, 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.
In one aspect of the invention, the light-emitting layer employs a technique of thermally activating delayed fluorescence emission. The host material of the light-emitting layer is selected from, but not limited to, one or more of the above-mentioned PH-1 to PH-85.
In one aspect of the invention, the light-emitting layer employs a technique of thermally activating delayed fluorescence emission. The luminescent layer fluorescent dopant thereof may be selected from, but is not limited to, one or more combinations of TDE1-TDE37 listed below.
In one aspect of the invention, an Electron Blocking Layer (EBL) is located between the hole transport layer and the light emitting layer. The electron blocking layer may employ, but is not limited to, one or more compounds of HT-1 through HT-51 described above, or one or more compounds of PH-47 through PH-77 described above; mixtures of one or more compounds of HT-1 through HT-51 and one or more compounds of PH-47 through PH-77 may also be employed, but are not limited thereto.
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.
An electron injection layer may also be included in the device between the electron transport layer and the cathode, the electron injection layer material including, but not limited to, a combination of one or more of the following.
LiQ, liF, naCl, csF, li 2O、Cs2CO3, baO, na, yb, li, ca, or Mg.
Examples
Mass spectrum characterization data in the following synthesis examples were obtained by ZAB-HS type mass spectrometer test manufactured by Micromass Co., UK.
Synthesis example 1
Synthesis of Compound P7
In a 1000mL single port flask, 15.00g of M1, 12.98g of 4-bromobiphenyl, 0.51g of dibenzyl acetone) dipalladium (0) (Pd 2(dba)3), 0.47g of 1, 3-bis (2, 6-diisopropylphenyl) imidazolium chloride (IPr.HCl), 16.06g of sodium tert-butoxide (NaOBu-t), 200mL of toluene, vacuum-pumping and nitrogen-exchanging are added, and the reaction is warmed to 90 ℃ for 5 hours. After the reaction, the reaction was stopped. Cooling to room temperature, separating the reaction liquid, purifying the organic phase by a silica gel column twice, concentrating the organic phase, adding methanol, refluxing and stirring for 1h, filtering to obtain pale yellow powder P7-1, and recrystallizing with ethyl acetate to obtain 19.77g of pure product.
P7-1: theoretical m/z value: 421; m/z found: 422.
To a 1000mL single port flask, 19.77g of P7-1, 15.71g of 2-bromo-9, 9-dideuteromethylfluorene, 0.86g of Pd 2(dba)3, 0.4mL of t-butylphosphine (t-Bu) 3 P, 13.52g of sodium t-butoxide and 300mL of toluene were added, the mixture was evacuated and purged with nitrogen for 3 times, and the reaction was warmed to 110℃for 5 hours. After the reaction, the reaction was stopped. Cooling to room temperature, separating the reaction solution, purifying the organic phase by a silica gel column twice, concentrating the organic phase, adding methanol, refluxing and stirring for 1h, filtering to obtain pale yellow powder P7, and recrystallizing with ethyl acetate for three times to obtain 13.52g of pure product.
Organic compound P7: theoretical m/z value: 619 (619); m/z found: 620.
Synthesis examples 2 to 24
The process routes of Synthesis examples 2 to 24 were the same as in Synthesis example 1, except that the raw materials were different, and the raw materials, the objective products and the results were represented as shown in Table 1.
Device embodiment
Based on the above synthesized specific compounds, the following device experiments were performed, in which the prior art compounds similar to the compounds of the present invention were introduced for technical comparison, and these comparative compounds (compounds numbered CCP) are all prior art, and their synthesis methods are not described in detail.
Example 1
The preparation process of the organic electroluminescent device in this embodiment is as follows: ultrasonic treating the glass plate coated with the ITO transparent conductive layer in a commercial cleaning agent, flushing in deionized water, ultrasonic degreasing in an acetone/ethanol mixed solvent, baking in a clean environment until the moisture is completely removed, cleaning with ultraviolet light and ozone, and bombarding the surface with a low-energy cation beam; placing the glass substrate with the anode in a vacuum cavity, vacuumizing to less than 1X 10 -5 Pa, and sequentially vacuum thermally evaporating 10nm of compound HT-4 to HI-3 (97/3,w/w) mixture serving as a hole injection layer, 60nm of compound HT-4 serving as a hole transport layer and 60nm of organic compound P7 serving as an electron blocking layer on the anode layer film; a 40nm binary mixture of a compound PH-35:RPD-8 (97/3,w/w) as a light-emitting layer; 5nm of ET-23 is used as a hole blocking layer, 25nm of compound ET-46:ET-57 (50/50, w/w) mixture is used as an electron transport layer, 0.5nm of LiF is used as an electron injection layer, and 150nm of metallic aluminum is used as a cathode; the total evaporation rate of all organic layers and LiF is controlled at 0.1nm/s, and the evaporation rate of the metal electrode is controlled at 1nm/s.
Examples 2 to 12
The following organic electroluminescent devices were prepared, which differ from example 1 only in that the electron blocking layer material organic compound P7 was replaced with P23, P52, P112, P183, P198, P397, P507, P547, P795, P820, P1256.
Comparative examples 1 to 4
An organic electroluminescent device differs from embodiment 1 only in that the electron blocking layer material organic compound P7 is replaced with CCP-1, CCP-2, CCP-3, CCP-4.CCP compounds are all known compounds, and the method for obtaining the CCP compounds is not described in detail.
The following performance tests were conducted on the organic electroluminescent devices provided in examples 1 to 12 and comparative examples 1 to 4 described above: the current efficiency of the organic electroluminescent device was measured using a digital source meter and a luminance meter at the same luminance. Specifically, the voltage is increased at a rate of 0.1V per second, and the current density when the brightness of the organic electroluminescent device reaches 3000cd/m 2 is measured, wherein the ratio of the brightness to the current density is the current efficiency; the lifetime test of LT97 is as follows: the time for the luminance of the organic electroluminescent device to drop to 2910cd/m 2 was measured using a luminance meter at 3000cd/m 2 luminance with reference material 1 as a reference.
The test results are shown in Table 2.
TABLE 2
| Examples numbering | Numbering of compounds | The required brightness cd/m 2 | Current efficiency cd/a | LT97 |
| Comparative example 1 | CCP-1 | 3000 | 17.9 | 1 |
| Comparative example 2 | CCP-2 | 3000 | 17.5 | 1.1 |
| Comparative example 3 | CCP-3 | 3000 | 16.3 | 0.8 |
| Comparative example 4 | CCP-4 | 3000 | 18.3 | 1.4 |
| Example 1 | P7 | 3000 | 18.4 | 1.6 |
| Example 2 | P23 | 3000 | 19.8 | 2.0 |
| Example 3 | P52 | 3000 | 20.2 | 2.1 |
| Example 4 | P112 | 3000 | 18.5 | 1.8 |
| Example 5 | P183 | 3000 | 18.6 | 1.6 |
| Example 6 | P198 | 3000 | 19.1 | 1.9 |
| Example 7 | P397 | 3000 | 19.2 | 1.8 |
| Example 8 | P507 | 3000 | 18.4 | 1.7 |
| Example 9 | P547 | 3000 | 18.6 | 1.6 |
| Example 10 | P795 | 3000 | 20.1 | 1.9 |
| Example 11 | P820 | 3000 | 19.7 | 2.0 |
| Example 12 | P1256 | 3000 | 20.0 | 2.2 |
As can be seen by combining the data in Table 2, the compound provided by the invention is used for an organic electroluminescent device, is more beneficial to improving the current efficiency and prolonging the service life of the device, so that the current efficiency of the device reaches 18.4-20.2cd/A, and the service life reaches 1.6-2.2 times of CCP-1, which indicates that the compound is an electron blocking layer material with good performance.
Example 13
The preparation method of the organic electroluminescent device comprises the following steps: ultrasonic treating the glass plate coated with the ITO transparent conductive layer in a commercial cleaning agent, flushing in deionized water, ultrasonic degreasing in an acetone/ethanol mixed solvent, baking in a clean environment until the moisture is completely removed, cleaning with ultraviolet light and ozone, and bombarding the surface with a low-energy cation beam; placing the glass substrate with the anode in a vacuum cavity, vacuumizing to less than 1X10 -5 Pa, and sequentially vacuum thermally evaporating 10nm of compound HT-4 to HI-3 (97/3,w/w) mixture on the anode layer film to serve as a hole injection layer, 60nm of compound HT-4 serving as a hole transport layer and 35nm of organic compound P580 serving as an electron blocking layer; a ternary mixture of 40nm of a compound PH-66:PH-3:GPD-12 (100:100:20, w/w) as a light-emitting layer; 5nm of ET-23 is used as a hole blocking layer, 25nm of compound ET-69:ET-57 (50/50, w/w) mixture is used as an electron transport layer, 1nm of LiF is used as an electron injection layer, and 150nm of metallic aluminum is used as a cathode; the total evaporation rate of all organic layers and LiF is controlled at 0.1nm/s, and the evaporation rate of the metal electrode is controlled at 1nm/s.
Examples 14 to 24
The following organic electroluminescent device was prepared, which differs from example 13 only in that the electron blocking layer material organic compound P580 was replaced with P697, P727, P939, P1111, P1132, P1135, P1255, P1351, P1491, P1675, P1698.
Comparative examples 5 to 8
An organic electroluminescent device differing from example 13 only in that the electron blocking layer material organic compound P580 was replaced with CCP-1, CCP-2, CCP-3, CCP-5.
The following performance tests were conducted on the organic electroluminescent devices provided in examples 13 to 24 and comparative examples 5 to 8 described above: the current efficiency of the organic electroluminescent device was measured using a digital source meter and a luminance meter at the same luminance. Specifically, the voltage is increased at a rate of 0.1V per second, and the current density when the brightness of the organic electroluminescent device reaches 10000cd/m 2 is measured, wherein the ratio of the brightness to the current density is the current efficiency; the lifetime test of LT97 is as follows: the time for the luminance of the organic electroluminescent device to drop to 9700cd/m 2 was measured using a luminance meter at 10000cd/m 2 luminance with reference material 1 as a reference.
TABLE 3 Table 3
As can be seen by combining the data in Table 3, the compound provided by the invention is used for an organic electroluminescent device, is more beneficial to improving the current efficiency and prolonging the service life of the device, so that the current efficiency of the device reaches 66.0-68.6cd/A, and the service life reaches 1.5-2.2 times of CCP-1, which indicates that the compound is an electron blocking layer material with good performance.
Compared with the comparative example 1, the compound ring A provided by the invention is selected from C7 or larger aromatic rings or heteroaromatic rings, so that the compound has better planeness and aromaticity, higher crystallinity and more compact space structure, which is favorable for hole transmission, thereby improving current efficiency and prolonging service life. Compared with comparative examples 2 and 3, the compound of the invention has aryl or heteroaryl at the ortho position of benzene ring connected with N, which is favorable for hole injection, and better balance between injection and migration is achieved, and the aromatic amine N is connected with the ortho position of aryl or heteroaryl, so that the molecular space structure is more compact, the film stacking form is good, and the stability and the film forming property are good. Compared with comparative examples 4 and 5, the hydrogen of methyl on dibenzo five-membered or six-membered heterocyclic ring connected with N is deuterium, and compared with H atom, the compound containing D atom has better thermodynamic stability and stronger tolerance to electrons, and can effectively prolong the service life of the device.
In summary, the invention is an electron blocking layer material with good performance, is suitable for red light or green light devices, can effectively improve the current efficiency of the devices and prolong the service life, and meanwhile, compared with H atoms, the compound containing D atoms has better thermodynamic stability.
We performed thermal stability tests on CCP-5 and P580: at the same test temperature, CCP-5 and P580 are sealed under vacuum (pressure <10 -5 Pa), and heated at the set temperature for 48h. The change in purity of the compounds before and after heating was tested by HPLC and the test results are shown in FIG. 1 (changes in purity of CCP-5 and P580 after vacuum sealing and heating at different temperatures for 48 hours). As can be seen from the figure, CCP-5 has a purity of 0.134% when heated at 330℃for 48 hours; and the purity of P580 changes by only 0.027% after heating at 330 ℃, which shows that the product has better thermal stability. It can be seen that the thermal stability of the compound can be effectively improved after the H atom of the methyl group on the 9, 9-dimethylfluorene is replaced by the D atom. The OLED material with high thermal stability can prevent the material from being decomposed under long-time heating, and can be applied to a large-scale evaporation production line.
While the invention has been described in connection with the embodiments, it is not limited to the above embodiments, but it should be understood that various modifications and improvements can be made by those skilled in the art under the guidance of the inventive concept, and the scope of the invention is outlined in the appended claims.
Claims (10)
1. An aromatic amine-type organic compound, characterized in that the organic compound has a structure represented by formula (I):
Wherein ring AR is selected from substituted or unsubstituted C7-C30 aryl, or substituted or unsubstituted C3-C30 heteroaryl;
A is a substituted or unsubstituted formula (a) wherein X is a single bond, O, S, NR 11 or CR 12R13;R11、R12、R13 is each independently hydrogen, deuterium, halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; r 12 and R 13 are linked to form a ring or are not linked to form a ring; in formula (a), CD 3 represents deuterated methyl;
L 1、L2 is independently a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group;
Ar 1、Ar2 is independently one of a substituted or unsubstituted C6-C60 aryl, a substituted or unsubstituted C3-C60 heteroaryl; provided that the Ar 2 substitution is ortho to the N atom substitution;
n is an integer of 1 to 4; r 4, which are the same or different, are each independently selected from hydrogen, deuterium, halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl, adjacent R 4 being linked to form a ring or not;
The substituted substituents are each independently selected from at least one of halogen, C1-C20 straight or branched 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; wherein the substituents of L 1 and Ar 1 are not perdeuterated alkyl groups;
The expression "represents a linking site" and "a" drawn ring structure indicates any position on the ring structure where a linking site can form a bond.
2. The aromatic amine-type organic compound according to claim 1, wherein,
L 1、L2 is independently one of a substituted or unsubstituted C6-C24 arylene, a substituent or an unsubstituted C3-C24 heteroarylene; the following substituted or unsubstituted structures are preferred:
The substituted substituents are each independently selected from at least one of halogen, C1-C20 straight or branched 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, ". A" connection site "-, indicates any position on the ring structure where a bond can be made,
Further preferably, each L 1 or L 2 is independently a substituted or unsubstituted group of:
3. The aromatic amine-type organic compound according to claim 1 or 2, wherein the ring AR is a C7-C12 aryl group,
Preferably ring AR is one of the following groups:
4. an aromatic amine-type organic compound according to claim 3, wherein the organic compound of formula (I) is represented by the structures represented by formulas (II) to (IV);
Wherein A, ar 1、Ar2、L1、L2 is as defined in formula (I),
R 1 is selected from hydrogen, substituted or unsubstituted C1-C10 chain alkyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C3-C30 heteroaryl, or R 1 is linked to the other C atoms of the benzene ring to which it is attached to form a ring structure;
R 1 is more preferably hydrogen.
5. The aromatic amine-type organic compound according to any one of claim 1 to 4, wherein,
Ar 1 is selected from the following groups, substituted or unsubstituted:
Wherein ". Smallcap" is a linking site, and each of A1 to A3 is independently one of a substituted or unsubstituted C1 to C30 chain alkyl, C3 to C20 cycloalkyl, C6 to C20 aryl, C5 to C20 heteroaryl, or a combination of at least two thereof;
When the above groups have substituents, the substituents are selected from one or a combination of at least two of C1-C12 chain alkyl, C3-C12 cycloalkyl, C2-C10 alkenyl, C1-C10 alkoxy or thioalkoxy, C6-C30 arylamino, C3-C30 heteroarylamino, C6-C30 aryl, and C3-C30 heteroaryl; further preferred substituents are methyl, tert-butyl, tert-amyl, cyclohexane, adamantyl, phenyl, tolyl, xylyl.
6. The aromatic amine-type organic compound according to any one of claim 1 to 5, wherein,
Ar 2 is independently C10-C30 aryl substituted or unsubstituted by R ', C3-C30 heteroaryl substituted or unsubstituted by R'; r' is a C1-C10 straight or branched alkyl group, a C3-C12 cycloalkyl group, a C2-C10 alkenyl group, a C6-C10 aryl group, a C3-C10 heteroaryl group,
Further preferably, ar 2 is the following group:
Further preferred Ar 2 is the following group:
7. A compound according to claim 5 or 6, characterized in that,
X is a single bond, O, CR 22R23;
R 22、R23 is independently H, methyl, phenyl, or R 22、R23 is connected to form cyclohexane ring, cyclopentane ring, dibenzocyclopentane ring;
n is 0, and the number of the n is 0,
L 1 and L 2 are each independently a single bond, naphthylene or phenylene.
8. The compound of claim 1, having any one of the structures shown below:
9. Use of an aromatic amine-type organic compound according to any one of claims 1 to 8 as a functional material in an organic electronic device comprising 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 scanner or electronic paper; preferably, the application is as an electron blocking layer material in an organic electroluminescent device.
10. 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 contain the compound according to any one of claims 1 to 8;
Preferably, the light-emitting functional layer includes at least one of an electron blocking layer, a hole transporting layer, or a hole injecting layer, and the compound according to any one of claims 1 to 8 is contained in at least one of the electron blocking layer, the hole transporting layer, or the hole injecting layer.
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