CN112125873A - Compound, hole transport material, organic electroluminescent device and display device - Google Patents
Compound, hole transport material, organic electroluminescent device and display device Download PDFInfo
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- CN112125873A CN112125873A CN202010935370.XA CN202010935370A CN112125873A CN 112125873 A CN112125873 A CN 112125873A CN 202010935370 A CN202010935370 A CN 202010935370A CN 112125873 A CN112125873 A CN 112125873A
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- 239000000463 material Substances 0.000 title claims abstract description 76
- 230000005525 hole transport Effects 0.000 title claims abstract description 53
- 150000001875 compounds Chemical class 0.000 title claims abstract description 45
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims abstract description 13
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 28
- -1 dibenzofuranyl Chemical group 0.000 claims description 24
- 150000003254 radicals Chemical class 0.000 claims description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 19
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 15
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 15
- 239000004305 biphenyl Substances 0.000 claims description 14
- 235000010290 biphenyl Nutrition 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 125000001624 naphthyl group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 12
- 125000005580 triphenylene group Chemical group 0.000 claims description 12
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 10
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 10
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 10
- 229910052805 deuterium Inorganic materials 0.000 claims description 10
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 10
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 10
- 125000005561 phenanthryl group Chemical group 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 150000004982 aromatic amines Chemical class 0.000 claims description 8
- 125000005549 heteroarylene group Chemical group 0.000 claims description 8
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 4
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001769 aryl amino group Chemical group 0.000 claims description 4
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 4
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 4
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000004306 triazinyl group Chemical group 0.000 claims description 4
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 claims description 2
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 2
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 claims description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical compound N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 claims description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 claims 1
- 125000000732 arylene group Chemical group 0.000 claims 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims 1
- 238000002347 injection Methods 0.000 abstract description 36
- 239000007924 injection Substances 0.000 abstract description 36
- 230000005012 migration Effects 0.000 abstract description 6
- 238000013508 migration Methods 0.000 abstract description 6
- 230000009286 beneficial effect Effects 0.000 abstract description 4
- 230000007704 transition Effects 0.000 abstract description 3
- 238000009825 accumulation Methods 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 119
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 74
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 63
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 44
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 33
- 239000007787 solid Substances 0.000 description 29
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 22
- 239000000843 powder Substances 0.000 description 21
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- 238000001953 recrystallisation Methods 0.000 description 20
- 238000001704 evaporation Methods 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- BIECSXCXIXHDBC-UHFFFAOYSA-N methyl 2-bromo-5-chlorobenzoate Chemical compound COC(=O)C1=CC(Cl)=CC=C1Br BIECSXCXIXHDBC-UHFFFAOYSA-N 0.000 description 14
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 14
- 230000008020 evaporation Effects 0.000 description 13
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 11
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- 238000000034 method Methods 0.000 description 11
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- 238000003786 synthesis reaction Methods 0.000 description 11
- 239000008096 xylene Substances 0.000 description 11
- 239000002019 doping agent Substances 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- 239000000758 substrate Substances 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 6
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 6
- 238000005406 washing Methods 0.000 description 5
- ZHQNDEHZACHHTA-UHFFFAOYSA-N 9,9-dimethylfluorene Chemical compound C1=CC=C2C(C)(C)C3=CC=CC=C3C2=C1 ZHQNDEHZACHHTA-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
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- 101000766357 Ruditapes philippinarum Big defensin Proteins 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
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- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- HATHNBZPXBWLFB-UHFFFAOYSA-N 1,3-dibromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=C(Br)C=CC=C1Br HATHNBZPXBWLFB-UHFFFAOYSA-N 0.000 description 2
- UCEGSRIJXCCEST-UHFFFAOYSA-N 2-bromo-3-chloronaphthalene Chemical compound C1=CC=C2C=C(Br)C(Cl)=CC2=C1 UCEGSRIJXCCEST-UHFFFAOYSA-N 0.000 description 2
- XLUAZLDTZYHVSO-UHFFFAOYSA-N 4-bromo-1-iodo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Br)=CC=C1I XLUAZLDTZYHVSO-UHFFFAOYSA-N 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L Cs2CO3 Substances [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
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- JOFBTOVNZIUWPX-UHFFFAOYSA-N dibenzofuran-1-ylboronic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2B(O)O JOFBTOVNZIUWPX-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
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- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
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- 238000007738 vacuum evaporation Methods 0.000 description 2
- GKWLILHTTGWKLQ-UHFFFAOYSA-N 2,3-dihydrothieno[3,4-b][1,4]dioxine Chemical compound O1CCOC2=CSC=C21 GKWLILHTTGWKLQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- SOODLDGRGXOSTA-UHFFFAOYSA-N 2-bromo-9-phenylcarbazole Chemical compound C=1C(Br)=CC=C(C2=CC=CC=C22)C=1N2C1=CC=CC=C1 SOODLDGRGXOSTA-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
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- 125000002091 cationic group Chemical group 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 238000005238 degreasing Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- JJMKWIWQQJZXDP-UHFFFAOYSA-N dibenzothiophen-1-ylboronic acid Chemical compound S1C2=CC=CC=C2C2=C1C=CC=C2B(O)O JJMKWIWQQJZXDP-UHFFFAOYSA-N 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
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- OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- GFTXWCQFWLOXAT-UHFFFAOYSA-M magnesium;cyclohexane;bromide Chemical compound [Mg+2].[Br-].C1CC[CH-]CC1 GFTXWCQFWLOXAT-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
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- 238000010295 mobile communication Methods 0.000 description 1
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- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-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
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
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Abstract
The invention provides a compound of general formula (I), which can be used in hole transport materials. The compound has a parent structure of fluorene fused ring linked ortho-substituted phenyl triarylamine, has high bond energy among atoms, good thermal stability, favorability for solid-state accumulation among molecules and strong transition capability of a hole. The organic electroluminescent device is applied to a hole transport layer, has a proper energy level with an adjacent layer, is beneficial to the injection and the migration of holes, can effectively reduce the driving voltage, has a high hole migration rate, and can effectively improve the luminous efficiency of the organic electroluminescent device. The invention also provides a hole transport material, an organic electroluminescent device and a display device containing the compound of the general formula (I).
Description
Technical Field
The invention relates to the field of organic light-emitting display, in particular to a compound, a hole transport material, an organic electroluminescent device and a display device.
Background
The organic electroluminescent display (hereinafter referred to as OLED) has a series of advantages of self-luminescence, low-voltage dc driving, full curing, wide viewing angle, light weight, simple composition and process, etc., and compared with the liquid crystal display, the organic electroluminescent display does not need a backlight source, and has a large viewing angle, low power, a response speed 1000 times that of the liquid crystal display, and a manufacturing cost lower than that of the liquid crystal display with the same resolution. Therefore, the organic electroluminescent device has very wide application prospect. With the continuous advance of OLED technology in both lighting and display areas, organic electroluminescent devices with good efficiency and long lifetime are generally the result of optimized matching of device structures and materials. The hole transport material, as an important functional material, has a direct influence on the mobility of holes, and ultimately influences the light emitting efficiency of the OLED. However, the hole transport materials currently used in OLEDs have low hole transport rates, poor energy level matching with adjacent layers, and no consideration for efficiency and lifetime, which severely restricts the display function and development of OLED display devices.
Disclosure of Invention
The invention aims to provide a compound which has strong hole transition capability and can effectively reduce the driving voltage of an organic electroluminescent device and improve the luminous efficiency when being used as a hole transport layer material.
In a first aspect, the present invention provides a compound having the structure of formula (I):
wherein,
Ar1and Ar2Each independently selected from C unsubstituted or substituted by Ra6-C30Aryl of (2), C unsubstituted or substituted by Ra3-C30The heteroaryl group of (a);
R1and R2Each independently selected from C1-C10Alkyl radical, C3-C6Cycloalkyl, C unsubstituted or substituted by Ra6-C30Aryl, C unsubstituted or substituted by Ra3-C30Heteroaryl of said R1And R2Can be connected into a ring;
R3-R6each independently selected from hydrogen, deuterium, C1-C10Alkyl radical, C3-C6Cycloalkyl, C unsubstituted or substituted by Ra6-C30Aryl, C unsubstituted or substituted by Ra3-C30Heteroaryl of said R3-R6Wherein two adjacent groups can be connected to form a ring;
x is selected from O, S, CR7R8、NR9，R7And R8Each independently selected from C1-C10Alkyl radical, C3-C6Cycloalkyl, C unsubstituted or substituted by Ra6-C30Aryl, C unsubstituted or substituted by Ra3-C30Heteroaryl radical, R7And R8Can be linked to form a ring, R9Selected from C unsubstituted or substituted by Ra6-C30Aryl of (2), C unsubstituted or substituted by Ra3-C30The heteroaryl group of (a);
l is selected from the group consisting of a bond, C unsubstituted or substituted by Ra6-C30Arylene, C unsubstituted or substituted by Ra3-C30A heteroarylene group;
each heteroatom in the heteroaryl or heteroarylene is independently selected from O, S, N;
the substituents Ra of each group are each independently selected from deuterium, halogen, nitro, cyano, C1-C4Alkyl, phenyl, biphenyl, terphenyl, naphthyl.
In a second aspect, the present invention provides a hole transport material comprising at least one of the compounds provided herein.
In a third aspect, the invention provides an organic electroluminescent device comprising at least one of the hole transport materials provided by the invention.
In a fourth aspect, the invention provides a display device comprising the organic electroluminescent device provided by the invention.
The compound provided by the invention has a parent structure of fluorene fused ring linked ortho-substituted phenyl triarylamine, has high bond energy among atoms and good thermal stability, is favorable for solid-state accumulation among molecules, and has strong transition capability of holes. The organic electroluminescent material is applied to a hole transport layer, has a proper energy level with an adjacent layer, is beneficial to the injection and the migration of holes, can effectively reduce the driving voltage, and can effectively improve the luminous efficiency of a device due to higher hole migration rate. In addition, the compound provided by the invention has the advantages of simple preparation process and easily obtained raw materials, and is suitable for industrial production.
Of course, not all of the advantages described above need to be achieved at the same time in the practice of any one product or method of the invention.
Drawings
In order to more clearly illustrate the embodiments or technical solutions in the prior art of the present invention, the drawings used in the description of the embodiments or prior art will be briefly described below, it is obvious that the drawings in the following description are only one embodiment of the present invention, and other embodiments can be obtained by those skilled in the art according to the drawings.
Fig. 1 is a schematic structural view of a typical organic electroluminescent device.
Detailed Description
The technical solutions in the present invention will be described clearly and completely with reference to the accompanying drawings, and it is obvious that the described embodiments are only some embodiments of the present invention, not all embodiments. All other embodiments obtained by a person skilled in the art based on the embodiments of the present invention belong to the protection scope of the present invention.
In a first aspect, the present invention provides a compound having the structure of formula (I):
wherein,
Ar1and Ar2Each independently selected from C unsubstituted or substituted by Ra6-C30Aryl of (2), C unsubstituted or substituted by Ra3-C30The heteroaryl group of (a);
R1and R2Each independently selected from C1-C10Alkyl radical, C3-C6Cycloalkyl, C unsubstituted or substituted by Ra6-C30Aryl, C unsubstituted or substituted by Ra3-C30Heteroaryl of said R1And R2Can be connected into a ring;
R3-R6each independently selected from hydrogen, deuterium, C1-C10Alkyl radical, C3-C6Cycloalkyl, C unsubstituted or substituted by Ra6-C30Aryl, C unsubstituted or substituted by Ra3-C30Heteroaryl of said R3-R6Wherein two adjacent groups can be connected to form a ring;
x is selected from O, S, CR7R8、NR9，R7And R8Each independently selected from C1-C10Alkyl radical, C3-C6Cycloalkyl, C unsubstituted or substituted by Ra6-C30Aryl, C unsubstituted or substituted by Ra3-C30Heteroaryl radical, R7And R8Can be connected into a ring; r9Selected from C unsubstituted or substituted by Ra6-C30Aryl of (2), C unsubstituted or substituted by Ra3-C30The heteroaryl group of (a);
l is selected from the group consisting of a bond, C unsubstituted or substituted by Ra6-C30Arylene, C unsubstituted or substituted by Ra3-C30A heteroarylene group;
each heteroatom in the heteroaryl or heteroarylene is independently selected from O, S, N;
each Ra is independently selected from deuterium, halogen, nitro, cyano, C1-C4Alkyl, phenyl, biphenyl, terphenyl, naphthyl.
Preferably, Ar1And Ar2Each independently selected from C unsubstituted or substituted by Ra6-C18Aryl of (2), C unsubstituted or substituted by Ra3-C15The heteroaryl group of (a);
preferably, R1And R2Each independently selected from C1-C6Alkyl radical, C3-C6Cycloalkyl, C unsubstituted or substituted by Ra6-C18Aryl, C unsubstituted or substituted by Ra3-C15Heteroaryl of said R1And R2Can be connected into a ring;
preferably, R3-R6Each independently selected from hydrogen, deuterium, C1-C6Alkyl radical, C3-C6Cycloalkyl, C unsubstituted or substituted by Ra6-C18Aryl, C unsubstituted or substituted by Ra3-C15Heteroaryl of said R3-R6Wherein two adjacent groups can be connected to form a ring;
preferably, R7And R8Each independently selected from C1-C6Alkyl radical, C3-C6Cycloalkyl, C unsubstituted or substituted by Ra6-C18Aryl, C unsubstituted or substituted by Ra3-C15Heteroaryl radical, R7And R8Can be connected into a ring;
preferably, R9Selected from C unsubstituted or substituted by Ra6-C18Aryl of (2), C unsubstituted or substituted by Ra3-C15The heteroaryl group of (a);
preferably, L is selected from the group consisting of a bond, C unsubstituted or substituted by Ra6-C18Arylene, C unsubstituted or substituted by Ra3-C15A heteroarylene group.
More preferably, Ar1And Ar2Each independently selected from the following unsubstituted or substituted with Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, arylamine, carbazolyl.
More preferably, R1And R2Each independently selected from methyl, ethyl, cyclopentyl, cyclohexyl, the following groups unsubstituted or substituted with Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, arylamine, carbazolyl.
More preferably, R3-R6Each independently selected from hydrogen, deuterium, methyl, ethyl, cyclopentyl, cyclohexyl, the following groups unsubstituted or substituted by Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, arylamine, carbazolyl.
More preferably, R7And R8Each independently selected from methyl, ethyl, cyclopentyl, cyclohexyl, the following groups unsubstituted or substituted with Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furyl, benzofuryl, dibenzofuryl, aza-dibenzofuryl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, arylamino, carbazolyl.
More preferably, R9Selected from the following unsubstituted or substituted by Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furyl, benzofuryl, dibenzofuryl, aza-dibenzofuryl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, arylamino, carbazolyl.
More preferably, L is selected from the group consisting of a bond, a subunit of the following compounds unsubstituted or substituted with Ra: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, pyridine, pyridazine, pyrimidine, pyrazine, quinoline, isoquinoline, quinazoline, quinoxaline, cinnoline, naphthyridine, triazine, pyridopyrazine, furan, benzofuran, dibenzofuran, aza-dibenzofuran, thiophene, benzothiophene, dibenzothiophene, aza-dibenzothiophene, 9-difluorene, spirofluorene, arylamine, carbazole.
For example, the compound of formula (I) is selected from the following structures A1-A30:
the compound provided by the invention has a parent structure of fluorene fused ring linked ortho-substituted phenyl triarylamine, has high bond energy among atoms and good thermal stability, and is beneficial to prolonging the service life of materials.
In a second aspect, the present invention provides a hole transport material comprising at least one of the compounds provided herein.
Fig. 1 shows a schematic view of a typical organic electroluminescent device, which includes an anode 2 and a cathode 8 on a substrate 1, and an organic material layer, which may be a multi-layered structure, between the anode 2 and the cathode 8. For example, the organic material layer may include a hole injection layer 3, a hole transport layer 4, a light emitting layer 5, an electron transport layer 6, and an electron injection layer 7.
It is to be understood that fig. 1 schematically shows the structure of a typical organic electroluminescent device, and the present invention is not limited to this structure, and the hole transport material of the present invention may be used in any type of organic electroluminescent device. For example, a typical organic electroluminescent device may further include an electron blocking layer, a hole blocking layer, a light extraction layer, etc., and in the present invention, these layers may be added or omitted according to actual needs.
In an organic electroluminescent device, a hole transport material has good electron donating property, a high HOMO energy level and high hole mobility, so that the transport of current carriers is facilitated, and the luminous efficiency of an OLED is improved.
The hole transport material provided by the invention has a parent structure of fluorene fused ring linked ortho-substituted phenyl triarylamine, and has high bond energy among atoms and good thermal stability, so that the service life of the hole transport material can be prolonged.
In a third aspect, the invention provides an organic electroluminescent device, which comprises at least one hole transport material provided by the invention applied to a hole transport layer. In the present invention, there is no limitation on the kind and structure of the organic electroluminescent device, and various types and structures of organic electroluminescent devices known in the art can be used as long as the hole transport material provided by the present invention can be used. Wherein the hole transport layer is disposed between the hole injection layer and the light emitting layer.
The organic electroluminescent device of the present invention may be a light-emitting device having a top emission structure, and examples thereof include a light-emitting device comprising an anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a transparent or translucent cathode in this order on a substrate. The thickness of the hole transport layer is 80-140 nm.
The organic electroluminescent element of the present invention may be a light-emitting element having a bottom emission structure, and may include a structure in which a transparent or translucent anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode are sequentially provided on a substrate.
The organic electroluminescent element of the present invention may be a light-emitting element having a double-sided light-emitting structure, and may include a structure in which a transparent or translucent anode, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a transparent or translucent cathode are sequentially provided on a substrate.
In addition, a hole injection layer may be provided between the anode electrode and the hole transport layer. An electron blocking layer is provided between the hole transport layer and the light emitting layer. A hole blocking layer is provided between the light emitting layer and the electron transport layer. An electron injection layer is provided between the electron transport layer and the cathode electrode. However, the structure of the organic electroluminescent device of the present invention is not limited to the above-described specific structure, and the above-described layers may be omitted or simultaneously provided, if necessary. For example, the organic electroluminescent device may comprise an anode made of metal, a hole injection layer (5-20nm), a hole transport layer (80-140nm), a light emitting layer (150-400nm), an electron transport layer (300-800nm), an electron injection layer (5-20nm), and a transparent or semitransparent cathode (50-80nm) in this order on a substrate.
In the organic electroluminescent device of the present invention, any material used for the layer as in the prior art can be used for the layer other than the hole transport layer comprising the hole transport material provided by the present invention.
The organic electroluminescent device of the present invention is described below with reference to fig. 1, but this is not meant to limit the scope of the present invention in any way. It is understood that all organic electroluminescent devices capable of using the hole transport material of the present invention are within the scope of the present invention. .
In the present invention, the substrate 1 is not particularly limited, and conventional substrates used in organic electroluminescent devices in the related art, for example, glass, polymer materials, and glass and polymer materials with TFT components and the like can be used.
In the present invention, the material of the anode 2 is not particularly limited, and may be selected from anode materials known in the art. For example, metals, alloys, conductive compounds, or the like have a high work function (4eV or more than 4 eV). More specifically, Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO)2) Transparent conductive materials such as zinc oxide (ZnO), metal materials such as silver and its alloys, aluminum and its alloys, organic conductive materials such as PEDOT (poly-3, 4-ethylenedioxythiophene), and multilayer structures of the above materials. Wherein the thickness of the anode 2 varies depending on the material used.
In the present invention, the material of the hole injection layer 3 is not particularly limited, and a hole injection material known in the art or a hole transport material provided by the present invention may be selected as the hole injection material. For example, the material of the hole injection layer may be selected from at least one of the following HT-1 to HT-32 compounds:
in the present invention, the hole injection layer 3 may further include a p-type dopant, the type of which is not particularly limited, and various p-type dopants known in the art may be employed, for example, the p-type dopant may be selected from at least one of the following compounds:
in the present invention, the amount of the p-type dopant is not particularly limited, and may be an amount well known to those skilled in the art.
In the present invention, the hole transport layer 4 contains at least one of the hole transport materials of the present invention. The hole transport layer 4 may also comprise any combination of at least one of the hole transport materials of the invention with known hole transport materials. The currently known hole transport material may be selected from at least one of the above-mentioned HT-1 to HT-32 compounds, but is not limited to the above-mentioned compounds.
The hole transport material provided by the invention has a fluorene fused ring linked ortho-substituted phenyl triarylamine parent structure, is applied to the hole transport layer 4, has a proper energy level with the adjacent layers, is beneficial to the injection and migration of holes, can effectively reduce the driving voltage, has a high hole migration rate, and can effectively improve the luminous efficiency of an organic electroluminescent device.
In the present invention, the light emitting material in the light emitting layer 5 is not particularly limited, and any light emitting material known to those skilled in the art may be used, and for example, the light emitting material may include a host material and a guest material. The host material may be selected from at least one of the following GPH-1 to GPH-80 compounds:
in a preferred embodiment of the invention, the light-emitting layer 5 employs the technique of electroluminescence. The guest material in the light-emitting layer 5 is a phosphorescent dopant, which may be selected from, but is not limited to, at least one of the following RPD-1 to RPD-28 compounds. The amount of the dopant is not particularly limited and may be an amount well known to those skilled in the art.
In the present invention, the material of the electron transport layer 6 is not particularly limited, and any electron transport material known to those skilled in the art may be used, for example, the electron transport material is selected from at least one of the ET-1 to ET-57 compounds listed below:
in the present invention, the electron transport layer 6 may further include an n-type dopant, the kind of which is not particularly limited, and various n-type dopants known in the art may be employed. For example, the n-type dopant may be a compound represented by the following formula:
in the present invention, the amount of the n-type dopant is not particularly limited, and may be an amount well known to those skilled in the art.
In the present invention, the material of the electron injection layer 7 is not particularly limited, and an electron injection material known in the art may be used, and for example, it may be selected from, but not limited to, LiQ, LiF, NaCl, CsF, Li in the prior art2O、Cs2CO3At least one of BaO, Na, Li, Ca and the like.
In the present invention, the material of the cathode 8 is not particularly limited, and may be selected from, but not limited to, metals such as Al, mg-ag mixture, LiF/Al, ITO, etc., metal mixtures, oxides, etc.
In a fourth aspect, the invention provides a display device comprising the organic electroluminescent device provided by the invention. The display device includes, but is not limited to, a display, a television, a mobile communication terminal, a tablet computer, and the like.
The method for preparing the organic electroluminescent device of the present invention is not particularly limited, and any method known in the art may be used, for example, the present invention may be prepared by the following preparation method:
(1) cleaning an anode 2 on an OLED device substrate 1 for top emission, respectively carrying out steps of medicinal washing, water washing, hairbrush, high-pressure water washing, air knife and the like in a cleaning machine, and then carrying out heat treatment;
(2) evaporating a hole injection layer 3 on the anode 2 in a vacuum evaporation mode;
(3) vacuum evaporating a hole transport material on the hole injection layer 3 to form a hole transport layer 4;
(4) a luminescent layer 5 is evaporated on the hole transport layer 4 in vacuum, wherein the luminescent layer 5 comprises a host material and a guest material;
(5) vacuum evaporating an electron transport material on the luminescent layer 5 to form an electron transport layer 6;
(6) an electron injection layer 7 is vacuum-deposited on the electron transport layer 6, and the material of the electron injection layer 7 is an electron injection material selected from LiQ, LiF, NaCl, CsF, and Li, for example2O、Cs2CO3One or more of BaO, Na, Li, Ca and other electron injection materials;
(7) a cathode material is vacuum-deposited on the electron injection layer 7 as a cathode 8.
The above description has been made of only a structure of a typical organic electroluminescent device and a method for fabricating the same, and it is to be understood that the present invention is not limited to this structure. The hole transport material of the present invention can be used for an organic electroluminescent device of any structure, and the organic electroluminescent device can be prepared by any preparation method known in the art.
Synthetic examples
Synthesis example 1: synthesis of Compound A1
Into a reaction flask were charged 100mmol of methyl 2-bromo-5-chlorobenzoate, 100mmol of 1-dibenzofuranboronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF (tetrahydrofuran), and 200ml of water, and 1 mol% of Pd (PPh) was added3)4(tetrakis (triphenylphosphine) palladium) was reacted at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain white powder M1.Wherein, Pd (PPh)3)4The amount of addition of (B) was 1 mol% based on methyl 2-bromo-5-chlorobenzoate.
100mmol of M1 and 200ml of THF are added into a reaction flask, 220mmol of methyl magnesium bromide is added dropwise at 0 ℃, and the temperature is raised to room temperature for reaction for 12 hours after the dropwise addition. After the reaction was completed, water was added, the organic phase was separated and concentrated to obtain intermediate M2.
100mmol of M2 and 200ml of trifluoromethanesulfonic anhydride were added to a reaction flask, heated to 120 ℃ and reacted for 12 hours. After the reaction, water was added to precipitate a solid, which was then filtered and dried to obtain intermediate M3.
100mmol of M3, 100mmol of 2- (9, 9-dimethylfluorene) -2-diamine, 28.83g of sodium tert-butoxide (300mmol), 800ml of xylene and 1 mol% of Pd (dba) (palladium bis-dibenzylideneacetone) are added to a reaction flask. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain a white powder a 1. Wherein Pd (dba) is added in an amount of 1 mol% based on M3.
1H NMR(400MHz,Chloroform)8.20(s,1H),7.96(dd,J＝12.0,8.0Hz,2H),7.88(d,J＝10.0Hz,2H),7.88(d,J＝10.0Hz,2H),7.69(s,1H),7.67(s,1H),7.59(d,J＝8.0Hz,4H),7.52(d,J＝7.6Hz,4H),7.39(ddd,J＝14.0,9.67.2Hz,4H),7.24(d,J＝8.0Hz,2H),7.14(s,1H),7.08(s,1H),1.69(s,12H).
M/Z: experimental value, 643.2; theoretical value, 643.3.
Synthesis example 2: synthesis of Compound A5
Into a reaction flask were charged 100mmol of methyl 2-bromo-5-chlorobenzoate, 100mmol of 1-dibenzofuranboronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4And reacting at 120 ℃ for 12 h. Stopping reaction after the reaction is finished, cooling the reactant to room temperature, adding water, filtering, washing with water, and recrystallizing and purifying the obtained solid with tolueneTo obtain a white powder M1. Wherein, Pd (PPh)3)4The amount of addition of (B) was 1 mol% based on methyl 2-bromo-5-chlorobenzoate.
100mmol of M2 and 200ml of trifluoromethanesulfonic anhydride were added to a reaction flask, heated to 120 ℃ and reacted for 12 hours. After the reaction, water was added to precipitate a solid, which was then filtered and dried to obtain intermediate M3.
100mmol of M2 and 200ml of THF are added into a reaction flask, 100mmol of methyl magnesium bromide is added dropwise at 0 ℃, and the temperature is raised to room temperature for reaction for 12 hours after the dropwise addition. After the reaction was completed, water was added, the organic phase was separated and concentrated to obtain intermediate M3.
100mmol of M3, 10ml of trifluoromethanesulfonic acid and 500ml of toluene were added to a reaction flask, and the mixture was heated to 120 ℃ and reacted for 12 hours. After the reaction, water was added to precipitate a solid, which was then filtered and dried to obtain intermediate M4.
100mmol of M4, 100mmol of 2- (9, 9-dimethylfluorene) -2-benzidine, 28.83g of sodium tert-butoxide (300mmol), 800ml of xylene and 1 mol% of Pd (dba) were added to the reaction flask and reacted at 120 ℃ for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain a white powder a 5. Wherein Pd (dba) is added in an amount of 1 mol% based on M4.
1H NMR(400MHz,Chloroform)8.20(s,1H),8.10(s,1H),7.99(d,J＝7.6Hz,2H),7.94(d,J＝10.0Hz,5H),7.86(s,1H),7.64(d,J＝12.0Hz,6H),7.58-7.49(m,6H),7.46–7.20(m,6H),7.14(s,1H),7.08(s,1H),2.28(s,3H),1.69(s,6H).
M/Z: experimental value, 704.9; theoretical value, 705.3.
Synthetic example 3: synthesis of Compound A13
Into a reaction flask were charged 100mmol of methyl 2-bromo-5-chlorobenzoate, 100mmol of 1-dibenzothiopheneboronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain white powder M1. Wherein, Pd (PPh)3)4The amount of addition of (B) was 1 mol% based on methyl 2-bromo-5-chlorobenzoate.
100mmol of M1 and 200ml of THF are added into a reaction flask, 220mmol of methyl magnesium bromide is added dropwise at 0 ℃, and the temperature is raised to room temperature for reaction for 12 hours after the dropwise addition. After the reaction was completed, water was added, the organic phase was separated and concentrated to obtain intermediate M2.
100mmol of M2 and 200ml of trifluoromethanesulfonic anhydride were added to a reaction flask, heated to 120 ℃ and reacted for 12 hours. After the reaction, water was added to precipitate a solid, which was then filtered and dried to obtain intermediate M3.
Into a reaction flask were charged 100mmol of 2-iodo-5-bromonitrobenzene, 100mmol of phenylboronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain white powder M4. Wherein, Pd (PPh)3)4The addition amount of (b) is 1 mol% of 2-iodo-5-bromonitrobenzene.
100mmol of M4 and 200mmol of iron powder and 200ml of glacial acetic acid are added into a reaction bottle, heated to 80 ℃ and reacted for 12 h. After the reaction was complete, water was added, extraction was carried out with ethyl acetate, and the organic phase was concentrated and dried to give intermediate M5.
Adding 100mmol of M5 and 200ml of acetonitrile into a reaction bottle, dropwise adding 120mmol of isoamyl nitrite and 120mmol of cuprous chloride, heating to 60 ℃ after dropwise adding, and reacting for 12 hours. After the reaction was completed, water was added, the organic phase was separated and concentrated to obtain intermediate M6.
100mmol of M6 and 500ml of THF are added into a reaction flask, 110mmol of cyclohexyl magnesium bromide are added dropwise at 0 ℃, and the temperature is raised to room temperature for reaction for 12 hours after the dropwise addition. After the reaction was completed, water was added, the organic phase was separated and concentrated to obtain intermediate M7.
100mmol of M7, 100mmol of 4-benzidine, 28.83g of sodium tert-butoxide (300mmol), 800ml of xylene and 1 mol% of Pd (dba) are added to a reaction flask and reacted at 120 ℃ for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain white powder M8. Wherein Pd (dba) is added in an amount of 1 mol% based on M7.
Into a reaction flask were charged 100mmol of M3, 100mmol of M8, 28.83g of sodium tert-butoxide (300mmol), 800ml of xylene, and 1 mol% of Pd (dba) were added. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain a white powder a 9. Wherein Pd (dba) is added in an amount of 1 mol% based on M3.
1H NMR(400MHz,Chloroform)8.45(s,1H),8.20-7.96(m,3H),7.74(d,J＝10.0Hz,4H),7.64–7.53(m,6H),7.48(d,J＝10.0Hz,3H),7.42(d,J＝10.0Hz,3H),7.37(d,J＝8.4Hz,4H),7.31(s,1H),7.08(s,1H),2.58(s,1H),1.99(s,2H),1.69(s,6H),1.60(s,4H),1.43(s,2H),1.12(s,2H).
M/Z: experimental value, 701.1; theoretical value, 701.3.
Synthetic example 4: synthesis of Compound A27
Into a reaction flask were charged 100mmol of methyl 2-bromo-5-chlorobenzoate, 100mmol of 4-carbazolyl boron ester, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4And reacting at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain white powder M1. Wherein, Pd (PPh)3)4The amount of addition of (B) was 1 mol% based on methyl 2-bromo-5-chlorobenzoate.
100mmol of M1 and 200ml of THF are added into a reaction flask, 220mmol of methyl magnesium bromide is added dropwise at 0 ℃, and the temperature is raised to room temperature for reaction for 12 hours after the dropwise addition. After the reaction was completed, water was added, the organic phase was separated and concentrated to obtain intermediate M2.
100mmol of M2 and 200ml of trifluoromethanesulfonic anhydride were added to a reaction flask, heated to 120 ℃ and reacted for 12 hours. After the reaction, water was added to precipitate a solid, which was then filtered and dried to obtain intermediate M3.
100mmol of M3, 100mmol of 2-bromo-9, 9-dimethylfluorene, 28.83g of sodium tert-butoxide (300mmol), 800ml of xylene and 1 mol% of Pd (dba) were added to a reaction flask and reacted at 120 ℃ for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain white powder M4. Wherein Pd (dba) is added in an amount of 1 mol% based on M3.
Into a reaction flask were charged 100mmol of 2, 6-dibromonitrobenzene, 200mmol of phenylboronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% Pd (PPh) was added3)4. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain white powder M5. Wherein, Pd (PPh)3)4The amount of (A) is 1 mol% of 2, 6-dibromonitrobenzene.
100mmol of M5 and 200mmol of iron powder and 200ml of glacial acetic acid are added into a reaction bottle, heated to 80 ℃ and reacted for 12 h. After the reaction, water was added, ethyl acetate was extracted, the organic phase was concentrated and dried to obtain intermediate M6.
100mmol of M6, 100mmol of N-phenyl-2-bromocarbazole, 28.83g of sodium tert-butoxide (300mmol), 800ml of xylene and 1 mol% of Pd (dba) are added to the reaction flask. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain white powder M7. Wherein Pd (dba) is added in an amount of 1 mol% based on M6.
Into a reaction flask were charged 100mmol of M4, 100mmol of M7, 28.83g of sodium tert-butoxide (300mmol), 800ml of xylene, and 1 mol% of Pd (dba) were added. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain a white powder a 9. Wherein Pd (dba) is added in an amount of 1 mol% based on M4.
1H NMR(400MHz,Chloroform)8.55(s,1H),8.19(d,J＝8.0Hz,4H),8.12(s,1H),7.97(d,J＝12.0Hz,2H),7.92–7.74(m,4H),7.72–7.56(m,8H),7.41(t,J＝7.6Hz,6H),7.37–7.26(m,4H),7.25(d,J＝8.4Hz,3H),7.20(dd,J＝14.4,8.0Hz,4H),7.09(d,J＝12.0Hz,4H),1.69(s,12H).
M/Z: experimental value, 959.2; theoretical value, 959.4.
Synthesis example 5: synthesis of Compound A11
Into a reaction flask were charged 100mmol of methyl 2-bromo-5-chlorobenzoate, 100mmol of 4- (9, 9-dimethylfluorene) -boronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water, and 1 mol% of Pd (PPh) was added3)4And reacting at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain white powder M1. Wherein, Pd (PPh)3)4The amount of addition of (B) was 1 mol% based on methyl 2-bromo-5-chlorobenzoate.
100mmol of M1 and 200ml of THF are added into a reaction flask, 220mmol of methyl magnesium bromide is added dropwise at 0 ℃, and the temperature is raised to room temperature for reaction for 12 hours after the dropwise addition. After the reaction was completed, water was added, the organic phase was separated and concentrated to obtain intermediate M2.
100mmol of M2 and 200ml of trifluoromethanesulfonic anhydride were added to a reaction flask, heated to 120 ℃ and reacted for 12 hours. After the reaction, water was added to precipitate a solid, which was then filtered and dried to obtain intermediate M3.
100mmol of M3, 100mmol of 2- (9, 9-dimethylfluorene) -2-diamine, 28.83g of sodium tert-butoxide (300mmol), 800ml of xylene and 1 mol% of Pd (dba) are added to a reaction flask and reacted at 120 ℃ for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain a white powder a 1. Wherein Pd (dba) is added in an amount of 1 mol% based on M3.
1H NMR(400MHz,Chloroform)8.20(s,1H),7.96(dd,J＝12.0,8.0Hz,2H),7.88(d,J＝10.0Hz,2H),7.88(d,J＝10.0Hz,2H),7.69(s,1H),7.67(s,1H),7.59(d,J＝8.0Hz,4H),7.52(d,J＝7.6Hz,4H),7.39(ddd,J＝14.0,9.67.2Hz,4H),7.24(d,J＝8.0Hz,2H),7.14(s,1H),7.08(s,1H),1.69(s,18H).
M/Z: experimental value, 669.2; theoretical value, 669.3.
Synthetic example 6: synthesis of Compound A23
100mmol of methyl 2-bromo-5-chlorobenzoate, 100mmol of 4- (9, 9-spirobifluorene) -boronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF and 200ml of water are charged in a reaction flask, and 1 mol% Pd (PPh)3)4And reacting at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain white powder M1. Wherein, Pd (PPh)3)4The amount of addition of (B) was 1 mol% based on methyl 2-bromo-5-chlorobenzoate.
100mmol of M1 and 200ml of trifluoromethanesulfonic anhydride were added to a reaction flask, heated to 120 ℃ and reacted for 12 hours. After the reaction, water was added to precipitate a solid, which was then filtered and dried to obtain intermediate M2.
Adding 100mmol of 2-bromo-2' -bromo-4-biphenyl and 200ml of THF into a reaction bottle, dropwise adding 110mmol of butyl lithium at-78 ℃, preserving heat for 30min after dropwise adding, cooling to-78 ℃, adding an intermediate M2, and naturally heating to room temperature for reaction for 12 h. After the reaction was completed, water was added, the organic phase was separated and concentrated to obtain intermediate M3.
100mmol of M3, 100mmol of 2- (2-dibenzofuran) -2-diamine, 28.83g of sodium tert-butoxide (300mmol), 800ml of xylene and 1 mol% of Pd (dba) are added to the reaction flask. The reaction was carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain a white powder a 23. Wherein Pd (dba) is added in an amount of 1 mol% based on M3.
1H NMR(400MHz,Chloroform)8.25–7.95(m,8H),7.98(s,2H),7.91–7.70(m,8H),7.65(s,3H),7.59(d,J＝12.8Hz,4H),7.50–7.19(m,11H),7.14(s,1H),7.08(s,3H),6.20(s,2H).
M/Z: experimental value, 887.2; theoretical value, 887.3.
Synthetic example 7: synthesis of Compound A21
Into a reaction flask were charged 100mmol of methyl 2-bromo-5-chlorobenzoate, 100mmol of 4- (9, 9-dimethylfluorene) -boronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF (tetrahydrofuran) and 200ml of water, and 1 mol% of Pd (PPh) was added3)4And reacting at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain white powder M1. Wherein, Pd (PPh)3)4The amount of addition of (B) was 1 mol% based on methyl 2-bromo-5-chlorobenzoate.
100mmol of M1 and 200ml of THF are added into a reaction flask, 220mmol of methyl magnesium bromide is added dropwise at 0 ℃, and the temperature is raised to room temperature for reaction for 12 hours after the dropwise addition. After the reaction was completed, water was added, the organic phase was separated and concentrated to obtain intermediate M2.
100mmol of M2 and 200ml of trifluoromethanesulfonic anhydride were added to a reaction flask, heated to 120 ℃ and reacted for 12 hours. After the reaction, water was added to precipitate a solid, which was then filtered and dried to obtain intermediate M3.
Into a reaction flask were charged 100mmol of 2-bromo-3-chloronaphthalene, 100mmol of phenylboronic acid, 41.4g of potassium carbonate (300mmol), 800ml of THF (tetrahydrofuran), and 200ml of water, and 1 mol% of Pd (PPh) was added3)4And reacting at 120 ℃ for 12 h. Stop after the reaction is finishedThe reaction was stopped and the reaction was cooled to room temperature, water was added, filtered and washed with water and the resulting solid was purified by recrystallization from toluene to give M4 as a white powder. Wherein, Pd (PPh)3)4The amount of the (B) is 1 mol% of the 2-bromo-3-chloronaphthalene.
100mmol of M4, 100mmol of 2- (9, 9-dimethylfluorene) -amine, 28.83g of sodium tert-butoxide (300mmol), 800ml of xylene are added to a reaction flask, and 1 mol% of Pd (dba) is added and the reaction is carried out at 120 ℃ for 12 h. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain white powder M5. Wherein Pd (dba) is added in an amount of 1 mol% based on M4.
100mmol of M3, 100mmol of M5, 28.83g of sodium tert-butoxide (300mmol), 800ml of xylene and 1 mol% of Pd (dba) are added to a reaction flask and reacted at 120 ℃ for 12 hours. After the reaction was completed, the reaction was stopped, and the reaction mixture was cooled to room temperature, water was added, filtered, washed with water, and the obtained solid was purified by recrystallization from toluene to obtain a white powder a 21. Wherein Pd (dba) is added in an amount of 1 mol% based on M3.
1H NMR(400MHz,Chloroform)8.20(s,1H),7.90-7.77(m,5H),7.70(s,1H),7.58(dd,J＝10.8,8.0Hz,4H),7.54(d,J＝8.4Hz,2H),7.40(ddd,J＝12.8,9.6,7.2Hz,6H),7.24-7.08(m,9H),1.69(s,18H).
M/Z: experimental value, 719.2; theoretical value, 719.3.
The compounds provided by the present invention can be synthesized by selecting suitable raw materials according to the ideas of examples 1 to 7, and can also be synthesized by selecting any other suitable methods and raw materials.
Example 1
Carrying out ultrasonic treatment on a glass plate coated with an Indium Tin Oxide (ITO) transparent conducting layer in a commercial cleaning agent, washing in deionized water, carrying out ultrasonic degreasing in an acetone-ethanol mixed solvent, baking in a clean environment until the moisture is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using a low-energy cationic beam;
then, the glass substrate with the anode is placed in a vacuum chamber and is vacuumized to be less than 10 DEG-5And (5) evaporating HT-11 as a hole injection layer on the anode layer film in vacuum at the evaporation rate of 0.1nm/s and the evaporation film thickness of 10nm, wherein the material of the hole injection layer is shown as the following formula:
vacuum evaporating an A1 material on the hole injection layer to form a hole transport layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 80 nm;
a luminescent layer is evaporated on the hole transport layer in vacuum, the luminescent layer comprises a main material GHP-16 and a dye material RPD-1, evaporation is carried out by a multi-source co-evaporation method, the evaporation rate of the main material GHP-16 is adjusted to be 0.1nm/s, the evaporation rate of the dye RPD-1 is 3% of the evaporation rate of the main material, and the total thickness of the evaporation film is 30 nm; the host material and the guest material are respectively the following materials:
vacuum evaporation is carried out on the light-emitting layer to form an electron transport layer, and a material ET-42 is selected as an electron transport material, wherein the evaporation rate is 0.1nm/s, and the total film thickness of evaporation is 30 nm; the electron transport material used is shown by the following formula:
and (3) vacuum evaporating an electron injection layer with the thickness of 0.5nm on the electron transport layer, wherein the evaporation rate is 0.1nm/s, and the material of the electron injection layer is lithium fluoride (LiF).
Finally, a cathode with the thickness of 150nm is evaporated on the electron injection layer, the evaporation rate is 0.1nm/s, the vacuum degree is 10-5And in torr, the cathode material is Al.
Examples 2 to 7
The procedure was as in example 1 except that A1 was replaced with A5, A9, A27, A6, A21 and A23 in Synthesis examples 2 to 7, respectively.
Comparative example 1
The procedure was as in example 1, except that HT-27 represented by the following formula was used in place of A1.
Method for testing performance of organic electroluminescent device
The organic electroluminescent devices obtained in examples and comparative examples were measured for driving voltage and current efficiency and lifetime at the same luminance using a digital source meter and a luminance meter, and specifically, the luminance of the organic electroluminescent devices reached 5000cd/m when the voltage was increased at a rate of 0.1V/sec2The current density is measured at the same time as the driving voltage; the ratio of the brightness to the current density is the current efficiency; the life test of LT95 is as follows: using a luminance meter at 5000cd/m2The luminance drop of the organic electroluminescent device was measured to be 4750cd/m by maintaining a constant current at luminance2Time in hours.
TABLE 1 comparison of device Performance in examples and comparative examples
As can be seen from the above data, the organic electroluminescent devices prepared in examples 1 to 7 were fabricated using the compounds a1, a5, a9, a27, a6, a21, and a23 provided by the present invention for the hole transport layer, and compared to comparative example 1 in which a material known in the art was used as the hole transport material of the organic electroluminescent device, the driving voltage was lower, the current efficiency was higher, and the life of LT95 was longer. Therefore, the compound is used as a hole transport material of an organic electroluminescent device, and the service life of the device can be effectively prolonged.
The above description is only for the preferred embodiment of the present invention, and is not intended to limit the scope of the present invention. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention shall fall within the protection scope of the present invention.
Claims (12)
1. A compound having the structure of formula (I):
wherein,
Ar1and Ar2Each independently selected from C unsubstituted or substituted by Ra6-C30Aryl of (2), C unsubstituted or substituted by Ra3-C30The heteroaryl group of (a);
R1and R2Each independently selected from C1-C10Alkyl radical, C3-C6Cycloalkyl, C unsubstituted or substituted by Ra6-C30Aryl, C unsubstituted or substituted by Ra3-C30Heteroaryl of said R1And R2Can be connected into a ring;
R3-R6each independently selected from hydrogen, deuterium, C1-C10Alkyl radical, C3-C6Cycloalkyl, C unsubstituted or substituted by Ra6-C30Aryl, C unsubstituted or substituted by Ra3-C30Heteroaryl of said R3-R6Wherein two adjacent groups can be connected to form a ring;
x is selected from O, S, CR7R8、NR9，R7And R8Each independently selected from C1-C10Alkyl radical, C3-C6Cycloalkyl, C unsubstituted or substituted by Ra6-C30Aryl, C unsubstituted or substituted by Ra3-C30Heteroaryl radical, R7And R8Can be linked to form a ring, R9Selected from C unsubstituted or substituted by Ra6-C30Aryl of (2), C unsubstituted or substituted by Ra3-C30The heteroaryl group of (a);
l is selected from the group consisting of a bond, C unsubstituted or substituted by Ra6-C30An arylene group,C unsubstituted or substituted by Ra3-C30A heteroarylene group;
each heteroatom in the heteroaryl or heteroarylene is independently selected from O, S, N;
the substituents Ra of each group are each independently selected from deuterium, halogen, nitro, cyano, C1-C4Alkyl, phenyl, biphenyl, terphenyl, naphthyl.
2. The compound of claim 1, wherein,
Ar1and Ar2Each independently selected from C unsubstituted or substituted by Ra6-C18Aryl of (2), C unsubstituted or substituted by Ra3-C15The heteroaryl group of (a);
R1and R2Each independently selected from C1-C6Alkyl radical, C3-C6Cycloalkyl, C unsubstituted or substituted by Ra6-C18Aryl, C unsubstituted or substituted by Ra3-C15Heteroaryl of said R1And R2Can be connected into a ring;
R3-R6each independently selected from hydrogen, deuterium, C1-C6Alkyl radical, C3-C6Cycloalkyl, C unsubstituted or substituted by Ra6-C18Aryl, C unsubstituted or substituted by Ra3-C15Heteroaryl of said R3-R6Wherein two adjacent groups can be connected to form a ring;
R7and R8Each independently selected from C1-C6Alkyl radical, C3-C6Cycloalkyl, C unsubstituted or substituted by Ra6-C18Aryl, C unsubstituted or substituted by Ra3-C15Heteroaryl radical, R7And R8Can be connected into a ring;
R9selected from C unsubstituted or substituted by Ra6-C18Aryl of (2), C unsubstituted or substituted by Ra3-C15The heteroaryl group of (a);
l is selected from the group consisting of a bond, unsubstituted orC substituted by Ra6-C18Arylene, C unsubstituted or substituted by Ra3-C15A heteroarylene group.
3. The compound of claim 1, wherein said Ar is1And Ar2Each independently selected from the following unsubstituted or substituted with Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, arylamine, carbazolyl.
4. The compound of claim 1, wherein R is1And R2Each independently selected from methyl, ethyl, cyclopentyl, cyclohexyl, the following groups unsubstituted or substituted with Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, arylamine, carbazolyl.
5. The compound of claim 1, wherein R is3-R6Each independently selected from hydrogen, deuterium, methyl, ethyl, cyclopentyl, cyclohexyl, the following groups unsubstituted or substituted by Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, arylamine, carbazolyl.
6. The compound of claim 1, wherein R is7And R8Each independently selected from methyl, ethyl, cyclopentyl, cyclohexyl, the following unsubstituted or substituted by Ra: phenyl, phenyl,Biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furanyl, benzofuranyl, dibenzofuranyl, aza-dibenzofuranyl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, arylamino, carbazolyl.
7. The compound of claim 1, wherein R is9Selected from the following unsubstituted or substituted by Ra: phenyl, biphenyl, terphenyl, naphthyl, phenanthryl, triphenylene, fluorenyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalinyl, cinnolinyl, naphthyridinyl, triazinyl, pyridopyrazinyl, furyl, benzofuryl, dibenzofuryl, aza-dibenzofuryl, thienyl, benzothienyl, dibenzothienyl, aza-dibenzothienyl, 9-dimethylfluorenyl, spirofluorenyl, arylamino, carbazolyl.
8. The compound of claim 1, wherein L is selected from a bond, a subunit of the following compound unsubstituted or substituted with Ra: benzene, biphenyl, terphenyl, naphthalene, phenanthrene, triphenylene, fluorene, pyridine, pyridazine, pyrimidine, pyrazine, quinoline, isoquinoline, quinazoline, quinoxaline, cinnoline, naphthyridine, triazine, pyridopyrazine, furan, benzofuran, dibenzofuran, aza-dibenzofuran, thiophene, benzothiophene, dibenzothiophene, aza-dibenzothiophene, 9-difluorene, spirofluorene, arylamine, carbazole.
9. The compound of claim 1 selected from the following structures a1-a 30:
10. a hole transport material comprising at least one compound of any one of claims 1-9.
11. An organic electroluminescent device comprising at least one of the hole transport materials of claim 10.
12. A display device comprising the organic electroluminescent device according to claim 11.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113292544A (en) * | 2021-05-25 | 2021-08-24 | 上海钥熠电子科技有限公司 | Aromatic amine compound and organic electroluminescent display device comprising the same |
| US20210355142A1 (en) * | 2021-04-23 | 2021-11-18 | Shanghai Tianma AM-OLED Co., Ltd. | Compound, material for an organic electroluminescent device and application thereof |
| CN113788807A (en) * | 2021-09-29 | 2021-12-14 | 京东方科技集团股份有限公司 | Fused ring aromatic amine compound for organic layer of OLED device and synthetic method and application thereof |
| CN115784903A (en) * | 2021-09-08 | 2023-03-14 | 中国石油化工股份有限公司 | Hole transport material and preparation method and application thereof |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014514344A (en) * | 2011-05-03 | 2014-06-19 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | Novel organic electroluminescent compound and organic electroluminescent device using the same |
| CN107223122A (en) * | 2015-02-16 | 2017-09-29 | 默克专利有限公司 | The material based on spirobifluorene derivative for electronic device |
| CN110698458A (en) * | 2019-10-30 | 2020-01-17 | 烟台显华化工科技有限公司 | Organic luminescent material and application thereof |
| CN111533716A (en) * | 2019-12-30 | 2020-08-14 | 南京高光半导体材料有限公司 | Fluorenyl organic electroluminescent compound and organic electroluminescent device |
| CN111548353A (en) * | 2020-05-26 | 2020-08-18 | 烟台显华化工科技有限公司 | Organic light-emitting material and organic electroluminescent device |
| CN111635324A (en) * | 2020-06-29 | 2020-09-08 | 南京高光半导体材料有限公司 | Organic electroluminescent compound and organic electroluminescent device |
-
2020
- 2020-09-08 CN CN202010935370.XA patent/CN112125873B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014514344A (en) * | 2011-05-03 | 2014-06-19 | ローム・アンド・ハース・エレクトロニック・マテリアルズ・コリア・リミテッド | Novel organic electroluminescent compound and organic electroluminescent device using the same |
| CN107223122A (en) * | 2015-02-16 | 2017-09-29 | 默克专利有限公司 | The material based on spirobifluorene derivative for electronic device |
| CN110698458A (en) * | 2019-10-30 | 2020-01-17 | 烟台显华化工科技有限公司 | Organic luminescent material and application thereof |
| CN111533716A (en) * | 2019-12-30 | 2020-08-14 | 南京高光半导体材料有限公司 | Fluorenyl organic electroluminescent compound and organic electroluminescent device |
| CN111548353A (en) * | 2020-05-26 | 2020-08-18 | 烟台显华化工科技有限公司 | Organic light-emitting material and organic electroluminescent device |
| CN111635324A (en) * | 2020-06-29 | 2020-09-08 | 南京高光半导体材料有限公司 | Organic electroluminescent compound and organic electroluminescent device |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20210355142A1 (en) * | 2021-04-23 | 2021-11-18 | Shanghai Tianma AM-OLED Co., Ltd. | Compound, material for an organic electroluminescent device and application thereof |
| US11905300B2 (en) * | 2021-04-23 | 2024-02-20 | Wuhan Tianma Micro-Electronics Co., Ltd. | Compound, material for an organic electroluminescent device and application thereof |
| CN113292544A (en) * | 2021-05-25 | 2021-08-24 | 上海钥熠电子科技有限公司 | Aromatic amine compound and organic electroluminescent display device comprising the same |
| CN115784903A (en) * | 2021-09-08 | 2023-03-14 | 中国石油化工股份有限公司 | Hole transport material and preparation method and application thereof |
| CN113788807A (en) * | 2021-09-29 | 2021-12-14 | 京东方科技集团股份有限公司 | Fused ring aromatic amine compound for organic layer of OLED device and synthetic method and application thereof |
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