CN118108607A - Triarylamine type organic compound, application thereof and organic electroluminescent device - Google Patents
Triarylamine type organic compound, application thereof and organic electroluminescent device Download PDFInfo
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- CN118108607A CN118108607A CN202311533066.2A CN202311533066A CN118108607A CN 118108607 A CN118108607 A CN 118108607A CN 202311533066 A CN202311533066 A CN 202311533066A CN 118108607 A CN118108607 A CN 118108607A
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- substituted
- unsubstituted
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- heteroaryl
- organic compound
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- 125000005259 triarylamine group Chemical group 0.000 title claims abstract description 6
- 150000002894 organic compounds Chemical class 0.000 title claims description 28
- 239000000463 material Substances 0.000 claims abstract description 70
- 150000001875 compounds Chemical class 0.000 claims abstract description 69
- -1 cyano, nitro, hydroxy, amino Chemical group 0.000 claims description 169
- 239000010410 layer Substances 0.000 claims description 114
- 125000001072 heteroaryl group Chemical group 0.000 claims description 37
- 230000000903 blocking effect Effects 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 18
- 125000001624 naphthyl group Chemical group 0.000 claims description 13
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 9
- 235000010290 biphenyl Nutrition 0.000 claims description 9
- 239000004305 biphenyl Substances 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical group 0.000 claims description 8
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 7
- 125000001769 aryl amino group Chemical group 0.000 claims description 7
- 229910052805 deuterium Inorganic materials 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
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000005592 polycycloalkyl group Polymers 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 150000002431 hydrogen 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
- 125000004648 C2-C8 alkenyl 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
- 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
- 239000002346 layers by function Substances 0.000 claims 3
- 238000005286 illumination Methods 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 230000000052 comparative effect Effects 0.000 description 30
- 230000005525 hole transport Effects 0.000 description 24
- 238000000034 method Methods 0.000 description 19
- 238000002347 injection Methods 0.000 description 16
- 239000007924 injection Substances 0.000 description 16
- 238000005516 engineering process Methods 0.000 description 13
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 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
- 230000009286 beneficial effect Effects 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 238000006243 chemical reaction Methods 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
- 239000011368 organic material Substances 0.000 description 8
- 125000001725 pyrenyl group Chemical group 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- 239000002019 doping agent Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 230000008569 process Effects 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
- 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
- 238000012360 testing method Methods 0.000 description 6
- 125000001544 thienyl group Chemical group 0.000 description 6
- 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
- 230000005540 biological transmission Effects 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 230000003111 delayed effect Effects 0.000 description 5
- 125000005561 phenanthryl group Chemical group 0.000 description 5
- 230000001105 regulatory effect Effects 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
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 4
- 125000004429 atom Chemical group 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
- 239000011521 glass Substances 0.000 description 4
- 125000001041 indolyl group Chemical group 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 4
- 239000012044 organic layer Substances 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
- 239000002994 raw material Substances 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 101100273664 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) ccp-1 gene Proteins 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 238000004770 highest occupied molecular orbital Methods 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 238000011056 performance test Methods 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000010189 synthetic method Methods 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
- QYNWFBYWVPMMRL-UHFFFAOYSA-N 1-bromo-4-(4-tert-butylphenyl)benzene Chemical group C1=CC(C(C)(C)C)=CC=C1C1=CC=C(Br)C=C1 QYNWFBYWVPMMRL-UHFFFAOYSA-N 0.000 description 2
- MBHPOBSZPYEADG-UHFFFAOYSA-N 2-bromo-9,9-dimethylfluorene Chemical compound C1=C(Br)C=C2C(C)(C)C3=CC=CC=C3C2=C1 MBHPOBSZPYEADG-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
- ZHQNDEHZACHHTA-UHFFFAOYSA-N 9,9-dimethylfluorene Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 ZHQNDEHZACHHTA-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
- 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
- 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
- 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
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 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
- 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
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000001816 cooling Methods 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
- 238000009792 diffusion process Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 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
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 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
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 2
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- 239000000843 powder Substances 0.000 description 2
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 2
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- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 2
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- 239000011593 sulfur Substances 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
- 238000002207 thermal evaporation Methods 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
- 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 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- KMZUUSFWPQLMQE-UHFFFAOYSA-N 1-bromo-9,9-dimethylfluorene Chemical compound C1=CC(Br)=C2C(C)(C)C3=CC=CC=C3C2=C1 KMZUUSFWPQLMQE-UHFFFAOYSA-N 0.000 description 1
- 125000006039 1-hexenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
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- LPTWEDZIPSKWDG-UHFFFAOYSA-N benzenesulfonic acid;dodecane Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCCCCCCCCCCC LPTWEDZIPSKWDG-UHFFFAOYSA-N 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
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- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
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- 238000013461 design Methods 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
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- 125000001033 ether group Chemical group 0.000 description 1
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
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- 238000007639 printing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- ZGNPLWZYVAFUNZ-UHFFFAOYSA-N tert-butylphosphane Chemical compound CC(C)(C)P ZGNPLWZYVAFUNZ-UHFFFAOYSA-N 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
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- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
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- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
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- C07D311/96—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings spiro-condensed with carbocyclic rings or ring systems
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- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
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Abstract
The invention provides a triarylamine type organic functional compound and application thereof, and the triarylamine type organic functional compound has a structure shown as a formula (I): The A group is a dibenzo five-membered ring or a six-membered ring structure; 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. Furthermore, in recent years, the demand for high refresh rate display panels has also been increasing, and it is also a problem to be solved if the corresponding speed of the luminescent material is increased.
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, 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 efficiency, prolong the service life of the device, and reduce capacitance, and its use.
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,
In the formula (I), the A group is a group in which the benzene ring of the dotted line represents the presence or absence,
X 1、X2 is a single bond, O, S, NR 11 or CR 12R13, and X 1 and X 2 are not both single bonds;
Ar 1 is a substituted or unsubstituted C10-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group;
Ar 2 and Ar 3 are each independently a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group;
l 1、L2 is each independently a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group;
R 1、R2、R4、R11、R12、R13 is hydrogen, deuterium, halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, C2-C8 alkenyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; adjacent R 1 or R 2 are linked to form a ring or not,
R 12 and R 13 are linked to form a ring or are not linked to form a ring;
R 3 is a substituted or unsubstituted C4-C20 chain alkyl, a substituted or unsubstituted C3-C20 cycloalkyl, a substituted or unsubstituted C4-C20 polycycloalkyl;
n is an integer of 1 to 6, m is an integer of 1 to 3, and p is an integer of 1 to 3;
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.
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; by introducing benzene rings or aromatic groups larger than the benzene rings at adjacent sites of the benzene rings in the formula (I), not only can the steric hindrance be regulated, but also the torsion degree of the molecule can be effectively regulated and controlled to reduce the crystallinity of the molecule; experiments show that larger Ar 1 can more obviously regulate and control the torsion degree of molecules to reduce the crystallinity of the molecules, and the groups are mutually matched, so that the stacking density of the 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 blocked from diffusing to a hole layer, so that an 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 driving voltage is reduced, and the comprehensive performance of the device is improved; the larger steric hindrance generated by R 3 can assist Ar 1 in adjusting the molecular stacking density to be more beneficial to prolonging the service life.
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 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, the A group is of the structure:
R 1 and R 2 are each independently selected from H, deuterium, methyl, tert-butyl, cyclohexane, phenyl, naphthyl, preferably R 1 and R 2 are H; adjacent R 1 or R 2 are linked to form a ring or not. The A group is easy to obtain synthetic raw materials, can well match with the HOMO orbit energy level of the whole compound, and meanwhile, the compound also has more suitable hole carrier transmission performance.
In a preferred embodiment of the invention, L 1 and L 2 are a single bond or a phenylene group, more preferably a single bond, preferably Ar 2 is each independently a substituted or unsubstituted C10-C30 aryl group.
As a further preferred embodiment of the present invention, it has a structure represented by formula (II),
Wherein X 1、X2、Ar2、Ar3、L1、L2、A、R4、R3 and p have the same meaning as that of formula (I);
l' is a substituted or unsubstituted C6-C24 aryl group, or a substituted or unsubstituted C3-C24 heteroaryl group; the following structure is further preferred:
R 21 is 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 C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;
Ar' is preferably a substituted or unsubstituted structure of:
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.
In a preferred embodiment of the invention, R 3 is a substituent having a tertiary carbon group, preferably a substituted or unsubstituted structure of the following:
R 4 is H, phenyl, biphenyl or naphthyl, preferably H. Based on a large amount of experimental data, the inventor discovers that by introducing aryl or heteroaryl at the adjacent site of benzene ring in the formula (I) and matching with the substituent with larger conjugation on Ar 1, electrons can be blocked from entering the transmission layer, and meanwhile, the capacitance of the compound after film formation can be properly reduced, which is beneficial to improving the quick response performance of the device.
In a preferred embodiment of the invention, ar 2 is a substituted or unsubstituted structure as follows:
Particularly preferred are the biphenyl groups described above, which can make the photoelectric properties of the compound more excellent.
L 2 is most preferably a single bond, and in a preferred embodiment of the invention Ar 3 is selected from the group consisting of substituted or unsubstituted:
Wherein the wavy line A1 to A3 are substituted or unsubstituted C1 to C30 chain alkyl, C3 to C20 cycloalkyl, C6 to C20 aryl, C5 to C20 heteroaryl groups, or combinations thereof, for the attachment site. When the above groups are substituted, the substituent is 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. Among these compounds, phenyl or substituted phenyl is preferable because phenyl or substituted phenyl does not excessively increase the molecular weight as a whole and increases the difficulty of synthesis when the molecular steric hindrance is sufficient.
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:
The organic compound provided by the application has a structure shown in a formula I, and through the design of a molecular structure, when larger aryl or heteroaryl (with carbon number more than or equal to 10) exists between N and alkyl, cycloalkyl or polycycloalkyl, the three-dimensional structure of the molecule can be effectively regulated, the stacking density of the molecule can be improved, and meanwhile, the refractive property of the molecule can be improved, so that the performance is improved. And the existence of alkyl, cycloalkyl or polycyclic alkyl can effectively prevent exciton from diffusing to holes, so that the stability of the device is improved and the service life is prolonged. When substituents exist at the ortho-position and meta-position of the benzene ring connected with N, the steric hindrance of the compound can be increased, which is beneficial to the lightening of LUMO energy level, so that the diffusion of excitons to a hole transport layer is further blocked, and the device performance is improved. Through further regulation and control, the transmission efficiency can be further improved, and the purposes of reducing voltage and prolonging service life are achieved. Meanwhile, the device disclosed by the application has lower capacitance, and in display application, the reduction of the capacitance of the OLED device is beneficial to shortening the charge and discharge process, and the brightness of the first frame is increased in the animation display process, so that bad display effects such as smear and the like are prevented. In addition, the preparation process of the compound is simple and easy to implement, raw materials are easy to obtain, and the compound is suitable for mass production and amplification. 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 of potential values for specific compounds and comparisons in examples.
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 for the organic compounds of the present application having the structure of formula I is shown below:
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, naOBu-t 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. For more specific synthetic methods, reference may be made to the synthetic examples described below, and those skilled in the art may generalize and practice the synthetic methods of other analogues in the generic terms of the specific modes of operation of the synthetic examples.
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.
The device may further include an electron injection layer between the electron transport layer and the cathode, the electron injection layer material including, but not limited to, a combination of one or more of the following: liQ, liF, naCl, csF, li 2O、Cs2CO3, baO, na, yb, li or Ca.
Examples
Synthesis example 1
Mass spectrum characterization data in the following synthesis examples were obtained by ZAB-HS type mass spectrometer test manufactured by Micromass Co., UK.
Synthesis of Compound P2
In a 1000mL single port flask, 15.00g of M1, 13.50g of 4-bromo-4' -tert-butylbiphenyl, 0.43g of dibenzyl acetone) dipalladium (0) (Pd 2(dba)3), 0.40g of 1, 3-bis (2, 6-diisopropylphenyl) imidazolium chloride (IPr.HCl), 13.45g of sodium tert-butoxide (NaOBu-t), 300mL of toluene, and the reaction was heated to 90℃for 5 hours by changing nitrogen to 3 times under vacuum. 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 P2-1, and recrystallizing with ethyl acetate to obtain 20.50g of pure product.
P2-1: theoretical m/z value: 529; m/z found: 530.
In a 1000mL single-necked flask, 20.50g of P2-1, 12.69g of 2-bromo-9, 9-dimethylfluorene, 0.35g of Pd 2(dba)3, 0.2mL of t-butylphosphine (t-Bu) 3 P, 11.16g of sodium t-butoxide and 300mL of toluene were added, the mixture was evacuated and nitrogen was replaced 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 P2, and recrystallizing with ethyl acetate three times to obtain pure 18.30g.
Organic compound P2: theoretical m/z value: 721; m/z found: 722.
Synthesis examples 2 to 14
Synthesis examples 2 to 14 were conducted in the same manner as in Synthesis example 1 except that M1 in Synthesis example 1 was changed to the intermediate shown by M-NH 2, 4-bromo-4' -tert-butylbiphenyl was changed to the intermediate shown by R 3-Ar1 -Br, and 2-bromo-9, 9-dimethylfluorene was changed to the intermediate shown by A-Br, as shown in Table 1.
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 the synthesis method thereof is not described in detail.
Example 1
The preparation process of the organic electroluminescent device in this embodiment is as follows:
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 1 multiplied by 10 < -5 > Pa, and sequentially performing vacuum thermal evaporation on the anode layer film to obtain a 10nm compound HT-4/HI-3 (97/3,w/w) mixture serving as a hole injection layer, a 60nm compound HT-4 serving as a hole transport layer and a 35nm organic compound P2 serving as an electron blocking layer; a ternary mixture of 40nm of a compound PH-61: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 2 to 6
An organic electroluminescent device differs from embodiment 1 only in that the electron blocking layer material organic compound P2 is replaced with P14, P57, P87, P553, P546.
Comparative examples 1 to 3
An organic electroluminescent device differs from embodiment 1 only in that the electron blocking layer material organic compound P2 is replaced with CCP-1, CCP-2, CCP-3.
The following performance tests were conducted on the organic electroluminescent devices provided in examples 2 to 6 and comparative examples 1 to 3 described above: the current efficiency and the lifetime of the organic electroluminescent devices of examples and comparative examples were measured at the same luminance using a digital source meter and a luminance meter. Specifically, the current density when the luminance of the organic electroluminescent device reached 10000cd/m2 was measured by boosting the voltage at a rate of 0.1V per second; the ratio of brightness to current density is the current efficiency;
the lifetime test of LT97 is as follows: the time, in hours, for the luminance of the organic electroluminescent device to decay to 97% of the original luminance was measured while maintaining a constant current (40 mA/cm 2).
The data obtained are summarized in Table 2, wherein each performance index of comparative example 1 was set to 100, and the performance of the other devices was relative to that of comparative example 1.
TABLE 2
| Device numbering | Numbering of compounds | Current efficiency | LT97 |
| Comparative example 1 | CCP-1 | 100 | 100 |
| Comparative example 2 | CCP-2 | 103 | 90 |
| Comparative example 3 | CCP-3 | 96 | 78 |
| Example 1 | P2 | 104 | 151 |
| Example 2 | P14 | 105 | 123 |
| Example 3 | P57 | 103 | 135 |
| Example 4 | P87 | 102 | 126 |
| Example 5 | P553 | 101 | 99 |
| Example 6 | P546 | 103 | 140 |
The data in Table 2 shows that the compound provided by the invention is used for the organic electroluminescent device, and is more beneficial to improving the current efficiency and prolonging the service life of the device. P2, P57, P87 are compared with CCP-1, P14 is compared with CCP-2, P553 is compared with CCP-3, when larger aryl or heteroaryl (with carbon number more than or equal to 10) exists between N and alkyl, cycloalkyl or polycycloalkyl, compared with benzene rings, the three-dimensional structure of molecules can be effectively regulated, the stacking density of the molecules can be improved, and meanwhile, the refractive property of the molecules can be improved, so that the performance of a device prepared by using the molecules can be further improved.
Example 7
An organic electroluminescent device was fabricated in the same manner as in example 1, except that the hole transport layer material was replaced with 105nm HT-28 and the electron blocking layer material organic compound P2 was replaced with P6.
Examples 8 to 10
An organic electroluminescent device has the same device structure and manufacturing process as in example 7, but replaces the electron blocking layer material organic compound P6 with P23, P30, P274.
Comparative examples 4 to 5
An organic electroluminescent device differing from example 7 only in that the electron blocking layer material organic compound P2 was replaced with CCP-4, CCP-5.
The following performance tests were performed on the organic electroluminescent devices provided in examples 7 to 10 and comparative examples 4 to 5 described above: the driving voltages of the organic electroluminescent devices of examples and comparative examples and the lifetimes of the devices were measured using a digital source meter and a luminance meter at the same luminance. Specifically, the voltage was raised at a rate of 0.1V per second, and the voltage when the luminance of the organic electroluminescent device reached 10000cd/m 2, i.e., the driving voltage, was measured;
The lifetime test of LT97 is as follows: the time, in hours, for the luminance of the organic electroluminescent device to decay to 97% of the original luminance was measured while maintaining a constant current (60 mA/cm 2).
The data obtained are summarized in Table 3, wherein each performance index of comparative example 4 was set to 100, and the performance of the other devices was relative to that of comparative example 4.
TABLE 3 Table 3
| Device numbering | Numbering of compounds | Drive voltage | LT97 |
| Comparative example 4 | CCP-4 | 100 | 100 |
| Comparative example 5 | CCP-5 | 101 | 72 |
| Example 7 | P6 | 98 | 120 |
| Example 8 | P23 | 97 | 125 |
| Example 9 | P30 | 96 | 132 |
| Example 10 | P274 | 97 | 122 |
The data in Table 3 shows that the compound provided by the invention is used for the organic electroluminescent device, and is more beneficial to reducing the driving voltage and prolonging the service life of the device. P6, P23, P30 compared to CCP-4, P274 compared to CCP-5, when dibenzofive-membered or dibenzosix-membered heterocycle is present as the group attached to N, this may be due to the dibenzoheterocycle having a better planar structure, resulting in reduced molecular crystallinity and improved molecular packing density. Meanwhile, through further regulation and control, the transmission efficiency can be further improved, and the purposes of reducing voltage and prolonging service life are achieved.
Example 11
The top emission type organic electroluminescent device was fabricated in the same manner as in example 11, except that the hole transport layer material was replaced with 105nm HT-28, the electron injection layer material LiF was replaced with 20nm Mg: ag (10:1) alloy, the cathode material Al was replaced with 70nm Ag, and the electron blocking layer material organic compound P2 was replaced with P165.
Example 12
An organic electroluminescent device differing from embodiment 11 only in that the electron blocking layer material organic compound P165 was replaced with P348.
Comparative examples 6 to 7
An organic electroluminescent device differing from embodiment 11 only in that the electron blocking layer material organic compound P165 was replaced with CCP-6, CCP-7.
The following performance tests were conducted on the organic electroluminescent devices provided in examples 11 to 12 and comparative examples 6 to 7 described above: the current efficiency and the lifetime of the organic electroluminescent devices of examples and comparative examples were measured at the same luminance using a digital source meter and a luminance meter. Specifically, the current density when the luminance of the organic electroluminescent device reached 10000cd/m 2 was measured by boosting the voltage at a rate of 0.1V per second; the ratio of brightness to current density is the current efficiency;
the lifetime test of LT97 is as follows: the time, in hours, for the luminance of the organic electroluminescent device to decay to 97% of the original luminance was measured while maintaining a constant current (40 mA/cm 2).
The data obtained are summarized in Table 4, wherein each performance index of comparative example 6 was set to 100, and the performance of the other devices was relative to that of comparative example 6.
TABLE 4 Table 4
| Device numbering | Numbering of compounds | Current efficiency | LT97 |
| Comparative example 6 | CCP-6 | 100 | 100 |
| Comparative example 7 | CCP-7 | 98 | 88 |
| Example 11 | P165 | 104 | 140 |
| Example 12 | P348 | 102 | 117 |
The data in Table 4 shows that the compound provided by the invention is used for the organic electroluminescent device, and is more beneficial to improving the efficiency and prolonging the service life of the device. P165 is compared with CCP-6, P348 is compared with CCP-7, substituents exist at the ortho-position and meta-position of the benzene ring connected with N at the same time, and compared with the substituents exist at the ortho-position and para-position of the benzene ring connected with N at the same time, the steric hindrance of the compound can be increased, which is beneficial to the lightening of the LUMO energy level, so that the diffusion of excitons to a hole layer is further blocked, and the device performance is improved.
Example 13
A top emission type organic electroluminescent device adopts a glass substrate plated with an Ag/ITO emission layer, the cleaning process is the same as that of the embodiment 1, the evaporation process of materials of all layers is the same, the hole injection layer, the hole blocking layer and the electron transport layer of the device are kept unchanged, but the hole transport layer material is replaced by 105nm HT-28, the electron injection layer material LiF is replaced by 1nm yttrium (Yb), the cathode material Al is replaced by 100nm Mg: ag (1:10) alloy, 85nm HT-21 is evaporated on the cathode again as a light extraction layer (CPL), and the electron blocking layer material is still an organic compound P2.
Examples 14 to 18
An organic electroluminescent device was constructed and fabricated in the same manner as in example 13, except that the electron blocking layer materials were replaced with P6, P23, P30, P72, and P589.
Comparative examples 8 to 9
An organic electroluminescent device having the same structure and manufacturing process as in example 13, but in which the electron blocking layer material was replaced with CCP-8, CCP-9.
The life test of LT97 was performed on the organic electroluminescent devices provided in examples 13 to 18 and comparative examples 8 to 9 described above as follows: the time, in hours, for the luminance of the organic electroluminescent device to decay to 97% of the original luminance was measured while maintaining a constant current (40 mA/cm 2). Meanwhile, capacitance test was also performed: the capacitance change of the device biased between-2V and 5V was measured using ac impedance, the results of which are shown in fig. 1, and the relative capacitance peaks are collected in table 5.
The data obtained are summarized in Table 5, wherein the performance index of comparative example 8 is set to 100 and the performance of the other devices is relative to that of comparative example 8.
TABLE 5
| Device numbering | Numbering of compounds | LT97 | Peak capacitance value |
| Comparative example 8 | CCP-8 | 100 | 100 |
| Comparative example 9 | CCP-9 | 84 | 113 |
| Example 13 | P2 | 120 | 59 |
| Example 14 | P6 | 105 | 64 |
| Example 15 | P23 | 112 | 69 |
| Example 16 | P30 | 117 | 87 |
| Example 17 | P72 | 111 | 60 |
| Example 18 | P589 | 107 | 88 |
As can be seen from the data in table 5, the compounds provided by the present invention are useful for organic electroluminescent devices, and are more useful for prolonging the service life of the devices. P2 and P72 are different from CCP-8, and P589 is different from CCP-9 in the presence of various alkyl groups, which can effectively prevent excitons from diffusing to holes, thereby improving the stability of the device and prolonging the service life. Meanwhile, we also found that the device capacitance of the present invention was lower relative to the comparative example, and as can be seen from FIG. 1, P2, P72 and P589 were significantly lower in capacitance relative to CCP-8 and CCP-9. In display application, the reduction of the capacitance of the OLED device is beneficial to shortening the charge-discharge process, increasing the brightness of the first frame in the animation display process, preventing bad display effects such as smear and the like, and improving the screen refresh rate.
In summary, the invention is an electron blocking layer material with good performance, is suitable for green light devices, can effectively reduce the driving voltage of the devices, improve the efficiency of the devices and prolong the service life, and can provide lower capacitance.
The applicant states that the present invention is illustrated by the above examples as a compound of the invention and its use, but the invention is not limited to, i.e. it is not meant that the invention must be practiced in dependence upon, the above examples. 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.
The present invention is described in detail by the above examples, but the present invention is not limited to the above detailed methods, i.e., it does not mean that the present invention must be practiced depending on the above detailed methods. 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 (10)
1. A triarylamine-type organic compound, characterized in that the organic compound has a structure represented by formula (I):
in the formula I, the A group is the following group,
X 1、X2 is a single bond, O, S, NR 11 or CR 12R13, and X 1 and X 2 are not both single bonds;
Ar 1 is a substituted or unsubstituted C10-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group;
Ar 2 and Ar 3 are each independently a substituted or unsubstituted C6-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group;
l 1、L2 is each independently a single bond, a substituted or unsubstituted C6-C30 arylene group, or a substituted or unsubstituted C3-C30 heteroarylene group;
R 1、R2、R4、R11、R12、R13 is hydrogen, deuterium, halogen, cyano, nitro, hydroxy, amino, substituted or unsubstituted C1-C20 chain alkyl, substituted or unsubstituted C3-C20 cycloalkyl, substituted or unsubstituted C2-C8 alkenyl, substituted or unsubstituted C1-C20 alkoxy, substituted or unsubstituted C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl; adjacent R 1 or R 2 are linked to form a ring or not,
R 12 and R 13 are linked to form a ring or are not linked to form a ring;
R 3 is a substituted or unsubstituted C4-C20 chain alkyl, a substituted or unsubstituted C3-C20 cycloalkyl, a substituted or unsubstituted C4-C20 polycycloalkyl;
n is an integer of 1 to 6, m is an integer of 1 to 3, and p is an integer of 1 to 3;
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,
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 triarylamine type organic compound of claim 1 wherein a group has the structure:
R 1、R2, m and n have the same meaning as that of formula (I),
Preferably, R 1 and R 2 are each independently selected from H, deuterium, methyl, tert-butyl, cyclohexane, phenyl, naphthyl;
More preferably, R 1 and R 2 are H.
3. Triarylamine-type organic compound according to claim 1 or 2, wherein L 1 and L 2 are a single bond or phenylene group, more preferably a single bond,
Preferably, ar 2 is independently a substituted or unsubstituted C10-C30 aryl group, or a substituted or unsubstituted C3-C30 heteroaryl group.
4. The triarylamine type organic compound according to claim 1 to 3, having a structure represented by formula (II),
Wherein X 1、X2、Ar2、Ar3、L1、L2、A、R4、R3 and p have the same meaning as that of formula (I);
l' is a substituted or unsubstituted C6-C24 aryl group, or a substituted or unsubstituted C3-C24 heteroaryl group; the following structure is further preferred:
R 21 is 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 C1-C20 silyl, substituted or unsubstituted C6-C60 arylamino, substituted or unsubstituted C3-C60 heteroarylamino, substituted or unsubstituted C6-C60 aryl, substituted or unsubstituted C3-C60 heteroaryl;
ar' is a substituted or unsubstituted structure of:
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.
5. The triarylamine-type organic compound as set forth in any one of claims 1-4 wherein R 3 is a substituent having a tertiary carbon group, preferably a substituted or unsubstituted structure of the following:
r 4 is H, phenyl, biphenyl or naphthyl, preferably H.
6. The triarylamine-type organic compound as set forth in any one of claims 1-4 wherein Ar 2 is a substituted or unsubstituted structure having the following structure:
7. The triarylamine-type organic compound according to any one of claims 1 to 6, wherein Ar 3 is selected from the group consisting of substituted or unsubstituted:
Wherein the wavy line For the linking site, A1 to A3 are each independently one of a substituted or unsubstituted C1 to C30 chain alkyl group, a C3 to C20 cycloalkyl group, a C6 to C20 aryl group, a C5 to C20 heteroaryl group, or a combination of at least two thereof
When the above groups are substituted, the substituent is 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.
8. The triarylamine-type organic compound as set forth in claim 1 having any one of the following structures:
9. Use of the triarylamine-type organic compound according to any one of claims 1 to 8 as a functional material in an organic electronic device including an organic electroluminescent device, an optical sensor, a solar cell, an illumination 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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| KR102321647B1 (en) * | 2017-03-14 | 2021-11-05 | 주식회사 동진쎄미켐 | Novel compound and organic electroluminescent divice including the same |
| CN113004154B (en) * | 2019-12-18 | 2024-05-17 | 北京鼎材科技有限公司 | Compound and application thereof |
| CN115028540B (en) * | 2021-04-02 | 2023-10-10 | 陕西莱特光电材料股份有限公司 | Organic electroluminescent material, electronic element and electronic device |
| CN115477587A (en) * | 2021-06-16 | 2022-12-16 | 北京鼎材科技有限公司 | Organic compound, application thereof and organic electroluminescent device comprising organic compound |
| CN115594702A (en) * | 2021-06-28 | 2023-01-13 | 北京鼎材科技有限公司（Cn） | Compound, application thereof and organic electroluminescent device |
| CN113511996B (en) * | 2021-07-20 | 2022-09-13 | 陕西莱特光电材料股份有限公司 | Organic electroluminescent material, electronic element and electronic device |
| CN114773210B (en) * | 2021-12-28 | 2024-04-23 | 北京鼎材科技有限公司 | Organic compound and application thereof |
| CN114933559A (en) * | 2022-06-17 | 2022-08-23 | 吉林奥来德光电材料股份有限公司 | Luminous auxiliary material and preparation method thereof, light-emitting device and light-emitting device |
| CN115304567B (en) * | 2022-10-10 | 2023-05-12 | 吉林奥来德光电材料股份有限公司 | Organic compound, preparation method thereof and organic electroluminescent device |
| CN116836136B (en) * | 2023-08-31 | 2023-12-01 | 吉林奥来德光电材料股份有限公司 | Luminescent auxiliary material and preparation method and application thereof |
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