CN113683517A - Aromatic amine derivative organic electroluminescent material and device thereof - Google Patents
Aromatic amine derivative organic electroluminescent material and device thereof Download PDFInfo
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- CN113683517A CN113683517A CN202010418297.9A CN202010418297A CN113683517A CN 113683517 A CN113683517 A CN 113683517A CN 202010418297 A CN202010418297 A CN 202010418297A CN 113683517 A CN113683517 A CN 113683517A
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- 239000000463 material Substances 0.000 title abstract description 49
- 150000004982 aromatic amines Chemical class 0.000 title abstract description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 113
- -1 pyrene compound Chemical class 0.000 claims abstract description 103
- 125000003118 aryl group Chemical group 0.000 claims abstract description 67
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims description 284
- 125000001424 substituent group Chemical group 0.000 claims description 85
- 239000010410 layer Substances 0.000 claims description 76
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- 125000001072 heteroaryl group Chemical group 0.000 claims description 43
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 41
- 229910052805 deuterium Inorganic materials 0.000 claims description 41
- 150000002431 hydrogen Chemical class 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 39
- 229910052736 halogen Inorganic materials 0.000 claims description 30
- 150000002367 halogens Chemical class 0.000 claims description 30
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 20
- 125000005104 aryl silyl group Chemical group 0.000 claims description 19
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 19
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 125000004104 aryloxy group Chemical group 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000002252 acyl group Chemical group 0.000 claims description 16
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 16
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 16
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 14
- 125000004185 ester group Chemical group 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 12
- 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 12
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 11
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 10
- 239000012044 organic layer Substances 0.000 claims description 10
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 8
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 8
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 125000005549 heteroarylene group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 8
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 8
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 7
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 6
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000002462 isocyano group Chemical group *[N+]#[C-] 0.000 claims description 6
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 6
- 229910052711 selenium Inorganic materials 0.000 claims description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 6
- 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 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 5
- 239000004305 biphenyl Substances 0.000 claims description 5
- DHFABSXGNHDNCO-UHFFFAOYSA-N dibenzoselenophene Chemical compound C1=CC=C2C3=CC=CC=C3[se]C2=C1 DHFABSXGNHDNCO-UHFFFAOYSA-N 0.000 claims description 5
- 238000009472 formulation Methods 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000005580 triphenylene group Chemical group 0.000 claims description 5
- 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 4
- KTQYWNARBMKMCX-UHFFFAOYSA-N tetraphenylene Chemical group C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C3=CC=CC=C3C2=C1 KTQYWNARBMKMCX-UHFFFAOYSA-N 0.000 claims 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 claims description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 abstract description 20
- BBEAQIROQSPTKN-UHFFFAOYSA-N antipyrene Natural products C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 abstract description 9
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 abstract description 7
- 238000006243 chemical reaction Methods 0.000 description 86
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 73
- 238000004440 column chromatography Methods 0.000 description 52
- 239000000047 product Substances 0.000 description 40
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 33
- 229910052757 nitrogen Inorganic materials 0.000 description 32
- 238000000746 purification Methods 0.000 description 29
- 239000007787 solid Substances 0.000 description 28
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 25
- 230000015572 biosynthetic process Effects 0.000 description 23
- 238000003786 synthesis reaction Methods 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 21
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 20
- 239000008096 xylene Substances 0.000 description 18
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 16
- 238000006467 substitution reaction Methods 0.000 description 16
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 14
- JRCJYPMNBNNCFE-UHFFFAOYSA-N 1,6-dibromopyrene Chemical compound C1=C2C(Br)=CC=C(C=C3)C2=C2C3=C(Br)C=CC2=C1 JRCJYPMNBNNCFE-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 230000003111 delayed effect Effects 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000012230 colorless oil Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000005457 ice water Substances 0.000 description 8
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 150000005347 biaryls Chemical group 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 238000002347 injection Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 6
- 238000005538 encapsulation Methods 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
- BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000004020 luminiscence type Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 230000005525 hole transport Effects 0.000 description 4
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 150000003220 pyrenes Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- YLKSTPDTTKOSIL-UHFFFAOYSA-N 2-methyl-5-phenylaniline Chemical compound C1=C(N)C(C)=CC=C1C1=CC=CC=C1 YLKSTPDTTKOSIL-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical compound C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 125000000477 aza group Chemical group 0.000 description 3
- DZBUGLKDJFMEHC-UHFFFAOYSA-N benzoquinolinylidene Natural products C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- OSQPUMRCKZAIOZ-UHFFFAOYSA-N carbon dioxide;ethanol Chemical compound CCO.O=C=O OSQPUMRCKZAIOZ-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000012634 fragment Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- WDAXFOBOLVPGLV-UHFFFAOYSA-N isobutyric acid ethyl ester Natural products CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 description 3
- 238000012544 monitoring process Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 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 3
- 238000002360 preparation method Methods 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 239000011669 selenium Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 2
- FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical compound CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- MUNOBADFTHUUFG-UHFFFAOYSA-N 3-phenylaniline Chemical compound NC1=CC=CC(C=2C=CC=CC=2)=C1 MUNOBADFTHUUFG-UHFFFAOYSA-N 0.000 description 2
- 229920001621 AMOLED Polymers 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-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
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
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- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 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
- NQFOGDIWKQWFMN-UHFFFAOYSA-N phenalene Chemical group C1=CC([CH]C=C2)=C3C2=CC=CC3=C1 NQFOGDIWKQWFMN-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 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
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000010200 validation analysis Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Abstract
Disclosed are an aromatic amine derivative organic electroluminescent material and a device thereof. The compound is an aromatic amine substituted pyrene compound, wherein the compound has a substituted or unsubstituted (hetero) aryl and penta (hetero) cyclic hydrocarbon and a substituted or unsubstituted bi (hetero) aryl aromatic amine structure, and can be used as a light-emitting material in an organic electroluminescent device. These novel compounds can provide better device performance such as higher external quantum efficiency and narrower half-peak width.
Description
Technical Field
The present invention relates to compounds for use in organic electronic devices, such as organic light emitting devices. And more particularly, to a pyrene compound substituted with an aromatic amine and an organic electroluminescent device and a compound formulation including the same.
Background
Organic electronic devices include, but are not limited to, the following classes: organic Light Emitting Diodes (OLEDs), organic field effect transistors (O-FETs), Organic Light Emitting Transistors (OLETs), Organic Photovoltaics (OPVs), dye-sensitized solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field effect devices (OFQDs), light emitting electrochemical cells (LECs), organic laser diodes, and organic plasma light emitting devices.
In 1987, Tang and Van Slyke of Islamic Kodak reported a two-layer organic electroluminescent device comprising an arylamine hole transport layer and a tris-8-hydroxyquinoline-aluminum layer as an electron transport layer and a light-emitting layer (Applied Physics Letters, 1987,51(12): 913-915). Upon biasing the device, green light is emitted from the device. The invention lays a foundation for the development of modern Organic Light Emitting Diodes (OLEDs). The most advanced OLEDs may comprise multiple layers, such as charge injection and transport layers, charge and exciton blocking layers, and one or more light emitting layers between the cathode and anode. Since OLEDs are a self-emissive solid state device, it offers great potential for display and lighting applications. Furthermore, the inherent properties of organic materials, such as their flexibility, may make them well suited for particular applications, such as in the fabrication of flexible substrates.
OLEDs can be classified into three different types according to their light emitting mechanisms. The OLEDs invented by Tang and van Slyke are fluorescent OLEDs. It uses only singlet luminescence. The triplet states generated in the device are wasted through the non-radiative decay channel. Therefore, the Internal Quantum Efficiency (IQE) of fluorescent OLEDs is only 25%. This limitation hinders the commercialization of OLEDs. In 1997, Forrest and Thompson reported phosphorescent OLEDs, which use triplet emission from complex-containing heavy metals as emitters. Thus, singlet and triplet states can be harvested, achieving 100% IQE. Due to its high efficiency, the discovery and development of phosphorescent OLEDs directly contributes to the commercialization of active matrix OLEDs (amoleds). Recently, Adachi has achieved high efficiency through Thermally Activated Delayed Fluorescence (TADF) of organic compounds. These emitters have a small singlet-triplet gap, making it possible for excitons to return from the triplet state to the singlet state. In TADF devices, triplet excitons are able to generate singlet excitons through reverse intersystem crossing, resulting in high IQE.
The light emitting color of the OLED can be realized by the structural design of the light emitting material. An OLED may comprise one light emitting layer or a plurality of light emitting layers to achieve a desired spectrum. Green, yellow and red OLED phosphorescent materials have been successfully commercialized. The existing phosphorescent blue OLED has the problems of short service life, difficulty in reaching deep blue, blue unsaturation, high working voltage and the like. The fluorescent blue OLED has a longer lifetime than the phosphorescent blue OLED, but has a low efficiency, and thus it is highly desirable to improve the efficiency and other properties of the fluorescent blue electroluminescent device.
WO2009107596A1 discloses triarylamine substituted pyrene compounds with benzo aliphatic ring, and the general formula of the compounds is
Wherein the substituent R21-R24Can be formed into a ring structure
Specifically, the following structure
The specific structure is disclosed as
And
however, the aromatic amines are not recognized in this patent applicationThe effect of introducing benzocyclohydrocarbons on device performance is also not disclosed and taught as having benzocyclohydrocarbon and biaryl structures that would enhance device performance.
CN107556239A discloses a pyrene compound containing an acridine structure, which has a general formula shown in the specification
Wherein Ar is1And Ar2Can be heterocyclic radical, and has specific structure
However, the application is mainly directed to a series of pyrene compounds with acridine substituted aromatic amine, and does not pay attention to improvement of device performance caused by benzo-heterocyclic hydrocarbon, and does not disclose and teach device effects obtained by introducing benzo-cyclic hydrocarbon or benzo-heterocyclic hydrocarbon into aromatic amine and using another aryl group in the aromatic amine as biaryl.
These documents disclose fluorescent light-emitting materials having an aromatic amine structure with pyrene as a core. However, the fluorescent light-emitting material still needs to be developed further to obtain higher device performance.
Disclosure of Invention
The present invention aims to solve at least part of the above problems by providing a novel series of pyrene-based compounds having an aromatic amine structure of a substituted or unsubstituted (hetero) aryl-fused five-membered (hetero) cyclic hydrocarbon and a substituted or unsubstituted di (hetero) aryl group.
According to one embodiment of the present invention, a compound having the structure of formula 1 is disclosed:
wherein, in the formula 1,
substituent R1-R10At least one of which has the structure of formula 2:
and the substituent R1-R10The remaining of (a) are, identically or differently on each occurrence, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof, having from 0 to 20 carbon atoms;
wherein, in the formula 2,
l is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 60 carbon atoms, or a combination thereof;
X1-X3selected from CR, identically or differently at each occurrencexOr N;
Y1and Y5Selected from CR, identically or differently at each occurrencey1Or N;
Y2-Y4selected from CR, identically or differently at each occurrencey2、CRy3Or N, and Y2-Y4At least one of which is CRy2；
Z is selected from C (R), identically or differently on each occurrencez)2，NRzO, S or Se;
Rx、Ry3and RzEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted having 1 to 20 carbon atomsA substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms, a substituted or unsubstituted heteroalkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 20 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 20 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof;
Ry1each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, and combinations thereof;
Ry2each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;
adjacent substituents Rx、Ry1、Ry3Can optionally be linked to form a ring;
substituent RzCan optionally be linked to form a ring;
and represents the position of the substituent with the structure of the formula 2 connected with the formula 1.
According to another embodiment of the present invention, there is also disclosed an electroluminescent device comprising the compound having the structure of formula 1. The specific structures of the compounds are described in the preceding examples.
According to another embodiment of the present invention, there is also disclosed a compound formulation comprising the compound having the structure of formula 1. Specific structures of the compounds are described in the preceding examples.
The invention provides a series of novel pyrene compounds with substituted or unsubstituted (hetero) aryl five-membered (hetero) cyclic hydrocarbon and substituted or unsubstituted bi (hetero) aryl aromatic amine structures, which can be used as luminescent materials in organic electroluminescent devices. These novel compounds can provide better device performance such as higher external quantum efficiency and narrower half-peak width.
Drawings
FIG. 1 is a schematic representation of an organic light emitting device that can contain the compounds and compound formulations disclosed herein.
Fig. 2 is a schematic view of another organic light emitting device that can contain compounds and compound formulations disclosed herein.
Detailed Description
OLEDs can be fabricated on a variety of substrates, such as glass, plastic, and metal. Fig. 1 schematically, but without limitation, illustrates an organic light emitting device 100. The figures are not necessarily to scale, and some of the layer structures in the figures may be omitted as desired. The device 100 may include a substrate 101, an anode 110, a hole injection layer 120, a hole transport layer 130, an electron blocking layer 140, an emissive layer 150, a hole blocking layer 160, an electron transport layer 170, an electron injection layer 180, and a cathode 190. The device 100 may be fabricated by sequentially depositing the described layers. The nature and function of the layers, as well as exemplary materials, are described in more detail in U.S. patent US7,279,704B2, columns 6-10, which is incorporated herein by reference in its entirety.
There are more instances of each of these layers. For example, a flexible and transparent substrate-anode combination is disclosed in U.S. Pat. No. 5,844,363, which is incorporated by reference in its entirety. An example of a p-doped hole transport layer is doped with F at a molar ratio of 50:14TCNQ m-MTDATA as disclosed in U.S. patent application publication No. 2003/0230980, which is incorporated by reference in its entirety. Examples of host materials are disclosed in U.S. patent No. 6,303,238 to Thompson et al, which is incorporated by reference in its entirety. An example of an n-doped electron transport layer is BPhen doped with Li at a molar ratio of 1:1, as in U.S. patent application publication No. 2003 @, which is incorporated by reference in its entirety0230980 to Kokai. U.S. Pat. Nos. 5,703,436 and 5,707,745, which are incorporated by reference in their entirety, disclose examples of cathodes including composite cathodes having a thin layer of a metal such as Mg: Ag and an overlying layer of transparent, conductive, sputter-deposited ITO. The principles and use of barrier layers are described in more detail in U.S. patent No. 6,097,147 and U.S. patent application publication No. 2003/0230980, which are incorporated by reference in their entirety. Examples of injection layers are provided in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety. A description of the protective layer may be found in U.S. patent application publication No. 2004/0174116, which is incorporated by reference in its entirety.
The above-described hierarchical structure is provided via non-limiting embodiments. The function of the OLED may be achieved by combining the various layers described above, or some layers may be omitted entirely. It may also include other layers not explicitly described. Within each layer, a single material or a mixture of materials may be used to achieve optimal performance. Any functional layer may comprise several sub-layers. For example, the light emitting layer may have two layers of different light emitting materials to achieve a desired light emission spectrum.
In one embodiment, an OLED may be described as having an "organic layer" disposed between a cathode and an anode. The organic layer may include one or more layers.
The OLED also requires an encapsulation layer, as shown in fig. 2, which is an exemplary, non-limiting illustration of an organic light emitting device 200, which differs from fig. 1 in that an encapsulation layer 102 may also be included over the cathode 190 to protect against harmful substances from the environment, such as moisture and oxygen. Any material capable of providing an encapsulation function may be used as the encapsulation layer, such as glass or a hybrid organic-inorganic layer. The encapsulation layer should be placed directly or indirectly outside the OLED device. Multilayer film encapsulation is described in U.S. patent US7,968,146B2, the entire contents of which are incorporated herein by reference.
Devices manufactured according to embodiments of the present invention may be incorporated into various consumer products having one or more electronic component modules (or units) of the device. Some examples of such consumer products include flat panel displays, monitors, medical monitors, televisions, billboards, lights for indoor or outdoor lighting and/or signaling, head-up displays, fully or partially transparent displays, flexible displays, smart phones, tablet computers, tablet handsets, wearable devices, smart watches, laptop computers, digital cameras, camcorders, viewfinders, micro-displays, 3-D displays, vehicle displays, and tail lights.
The materials and structures described herein may also be used in other organic electronic devices as previously listed.
As used herein, "top" means furthest from the substrate, and "bottom" means closest to the substrate. Where a first layer is described as being "disposed on" a second layer, the first layer is disposed farther from the substrate. Other layers may be present between the first and second layers, unless it is specified that the first layer is "in contact with" the second layer. For example, a cathode can be described as being "disposed on" an anode even though various organic layers are present between the cathode and the anode.
As used herein, "solution processable" means capable of being dissolved, dispersed or transported in and/or deposited from a liquid medium in the form of a solution or suspension.
A ligand may be referred to as "photoactive" when it is believed that the ligand directly contributes to the photoactive properties of the emissive material. A ligand may be referred to as "ancillary" when it is believed that the ligand does not contribute to the photoactive properties of the emissive material, but the ancillary ligand may alter the properties of the photoactive ligand.
It is believed that the Internal Quantum Efficiency (IQE) of fluorescent OLEDs can be limited by delaying fluorescence beyond 25% spin statistics. Delayed fluorescence can generally be divided into two types, i.e., P-type delayed fluorescence and E-type delayed fluorescence. P-type delayed fluorescence results from triplet-triplet annihilation (TTA).
On the other hand, E-type delayed fluorescence does not depend on collision of two triplet states, but on conversion between triplet and singlet excited states. Compounds capable of producing E-type delayed fluorescence need to have a very small mono-triplet gap in order to switch between energy states. Thermal energy can activate a transition from a triplet state back to a singlet state. This type of delayed fluorescence is also known as Thermally Activated Delayed Fluorescence (TADF). A significant feature of TADF is that the retardation component increases with increasing temperature. If the reverse intersystem crossing (IRISC) rate is fast enough to minimize non-radiative decay from the triplet state, then the fraction of the backfill singlet excited state may reach 75%. The total singlet fraction may be 100%, far exceeding 25% of the spin statistics of the electrogenerated excitons.
The delayed fluorescence characteristic of type E can be found in excited complex systems or in single compounds. Without being bound by theory, it is believed that E-type delayed fluorescence requires the light emitting material to have a small mono-triplet energy gap (Δ Ε)S-T). Organic non-metal containing donor-acceptor emissive materials may be able to achieve this. The emission of these materials is generally characterized as donor-acceptor Charge Transfer (CT) type emission. Spatial separation of HOMO from LUMO in these donor-acceptor type compounds generally results in small Δ ES-T. These states may include CT states. Generally, donor-acceptor light emitting materials are constructed by linking an electron donor moiety (e.g., an amino or carbazole derivative) to an electron acceptor moiety (e.g., a six-membered, N-containing, aromatic ring).
Definitions for substituent terms
Halogen or halide-as used herein, includes fluorine, chlorine, bromine and iodine.
Alkyl-comprises both straight and branched chain alkyl groups. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, neopentyl, 1-methylpentyl, 2-methylpentyl, 1-pentylhexyl, 1-butylpentyl, 1-heptyloctyl, 3-methylpentyl. In addition, the alkyl group may be optionally substituted. The carbons in the alkyl chain may be substituted with other heteroatoms. Among the above, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl and neopentyl are preferable.
Cycloalkyl-as used herein, comprises a cyclic alkyl group. Preferred cycloalkyl groups are those containing 4 to 10 ring carbon atoms and include cyclobutyl, cyclopentyl, cyclohexyl, 4-methylcyclohexyl, 4, 4-dimethylcyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, 2-norbornyl and the like. In addition, the cycloalkyl group may be optionally substituted. The carbon in the ring may be substituted with other heteroatoms.
Alkenyl-as used herein, encompasses both straight and branched chain olefinic groups. Preferred alkenyl groups are those containing 2 to 15 carbon atoms. Examples of the alkenyl group include a vinyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a1, 3-butadienyl group, a 1-methylvinyl group, a styryl group, a 2, 2-diphenylvinyl group, a 1-methylallyl group, a1, 1-dimethylallyl group, a 2-methylallyl group, a 1-phenylallyl group, a 3, 3-diphenylallyl group, a1, 2-dimethylallyl group, a 1-phenyl-1-butenyl group and a 3-phenyl-1-butenyl group. In addition, alkenyl groups may be optionally substituted.
Alkynyl-as used herein, straight and branched alkynyl groups are contemplated. Preferred alkynyl groups are those containing 2 to 15 carbon atoms. In addition, alkynyl groups may be optionally substituted.
Aryl or aromatic-as used herein, non-fused and fused systems are contemplated. Preferred aryl groups are those containing from 6 to 60 carbon atoms, more preferably from 6 to 20 carbon atoms, and even more preferably from 6 to 12 carbon atoms. Examples of aryl groups include phenyl, biphenyl, terphenyl, triphenylene, tetraphenylene, naphthalene, anthracene, phenalene, phenanthrene, fluorene, pyrene, chicory, perylene and azulene, preferably phenyl, biphenyl, terphenyl, triphenylene, fluorene and naphthalene. In addition, the aryl group may be optionally substituted. Examples of non-fused aryl groups include phenyl, biphenyl-2-yl, biphenyl-3-yl, biphenyl-4-yl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-triphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-tolyl, m-tolyl, p-tolyl, p- (2-phenylpropyl) phenyl, 4 '-methyldiphenyl, 4' -tert-butyl-p-terphenyl-4-yl, o-cumyl, m-cumyl, p-cumyl, 2, 3-xylyl, 3, 4-xylyl, 2, 5-xylyl, mesityl and m-quaterphenyl.
Heterocyclyl or heterocyclic-as used herein, aromatic and non-aromatic cyclic groups are contemplated. Heteroaryl also refers to heteroaryl. Preferred non-aromatic heterocyclic groups are those containing 3 to 7 ring atoms, which include at least one heteroatom such as nitrogen, oxygen and sulfur. The heterocyclic group may also be an aromatic heterocyclic group having at least one hetero atom selected from a nitrogen atom, an oxygen atom, a sulfur atom and a selenium atom.
Heteroaryl-as used herein, non-fused and fused heteroaromatic groups are contemplated which may contain 1 to 5 heteroatoms. Preferred heteroaryl groups are those containing from 3 to 30 carbon atoms, more preferably from 3 to 20 carbon atoms, more preferably from 3 to 12 carbon atoms. Suitable heteroaryl groups include dibenzothiophene, dibenzofuran, dibenzoselenophene, furan, thiophene, benzofuran, benzothiophene, benzoselenophene, carbazole, indolocarbazole, pyridine indole, pyrrolopyridine, pyrazole, imidazole, triazole, oxazole, thiazole, oxadiazole, bisoxazole, thiadiazole, pyridine, pyridazine, pyrimidine, pyrazine, triazine, oxazine, oxathiazine, oxadiazine, indoline, benzimidazole, indazole, indenozine, benzoxazole, benzisoxazole, benzothiazole, quinoline, isoquinoline, cinnoline, quinazoline, quinoxaline, naphthyridine, phthalazine, pteridine, xanthene, acridine, phenazine, phenothiazine, benzothienopyridine, thienobipyridine, benzothiophenopyridine, cinnolinopyrimidine, selenobenzodipyridine, selenobenzene, preferably dibenzothiophene, dibenzofuran, dibenzoselenophene, carbazole, indolocarbazole, imidazole, pyridine, triazine, benzimidazole, 1, 2-azaborine, 1, 3-azaborine, 1, 4-azaborine, borazole, and aza analogues thereof. In addition, the heteroaryl group may be optionally substituted.
Alkoxy-is represented by-O-alkyl. Examples and preferred examples of the alkyl group are the same as those described above. Examples of the alkoxy group having 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms include methoxy, ethoxy, propoxy, butoxy, pentyloxy and hexyloxy. The alkoxy group having 3 or more carbon atoms may be linear, cyclic or branched.
Aryloxy-is represented by-O-aryl or-O-heteroaryl. Examples and preferred examples of aryl and heteroaryl groups are the same as described above. Examples of the aryloxy group having 6 to 40 carbon atoms include a phenoxy group and a biphenyloxy group.
Aralkyl-as used herein, an alkyl group having an aryl substituent. In addition, the aralkyl group may be optionally substituted. Examples of the aralkyl group include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α -naphthylmethyl, 1- α -naphthylethyl, 2- α -naphthylethyl, 1- α -naphthylisopropyl, 2- α -naphthylisopropyl, β -naphthylmethyl, 1- β -naphthylethyl, 2- β -naphthylethyl, 1- β -naphthylisopropyl, 2- β -naphthylisopropyl, p-methylbenzyl, m-methylbenzyl, o-methylbenzyl, p-chlorobenzyl, m-chlorobenzyl, o-chlorobenzyl, p-bromobenzyl, m-bromobenzyl, o-bromobenzyl, p-iodobenzyl, m-iodobenzyl, o-iodobenzyl, p-hydroxybenzyl, m-hydroxybenzyl, o-hydroxybenzyl, p-aminobenzyl, m-aminobenzyl, o-aminobenzyl, p-nitrobenzyl, m-nitrobenzyl, o-nitrobenzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-2-hydroxy-2-phenylisopropyl and 1-chloro-2-phenylisopropyl. Among the above, benzyl, p-cyanobenzyl, m-cyanobenzyl, o-cyanobenzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl and 2-phenylisopropyl are preferable.
The term "aza" in azafluorene, azaspirobifluorene ring, azadibenzofuran, aza-dibenzothiophene, etc., means that one or more C-H groups in the corresponding aromatic moiety are replaced by a nitrogen atom. For example, azatriphenylenes include dibenzo [ f, h ] quinoxalines, dibenzo [ f, h ] quinolines, and other analogs having two or more nitrogens in the ring system. Other nitrogen analogs of the above-described aza derivatives may be readily envisioned by one of ordinary skill in the art, and all such analogs are intended to be encompassed within the terms described herein.
In this disclosure, unless otherwise defined, when any one of the terms in the group consisting of: substituted alkyl, substituted cycloalkyl, substituted heteroalkyl, substituted aralkyl, substituted alkoxy, substituted aryloxy, substituted alkenyl, substituted aryl, substituted heteroaryl, substituted alkylsilyl, substituted arylsilyl, substituted amino, substituted acyl, substituted carbonyl, substituted carboxylic acid, substituted ester, substituted sulfinyl, substituted sulfonyl, substituted phosphino, meaning alkyl, cycloalkyl, heteroalkyl, aralkyl, alkoxy, aryloxy, alkenyl, aryl, heteroaryl, alkylsilyl, arylsilyl, amino, acyl, carbonyl, carboxylic acid, ester, sulfinyl, sulfonyl and phosphino, any of which groups may be substituted with one or more members selected from deuterium, unsubstituted alkyl having 1 to 20 carbon atoms, unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, an unsubstituted heteroalkyl group having from 1 to 20 carbon atoms, an unsubstituted aralkyl group having from 7 to 30 carbon atoms, an unsubstituted alkoxy group having from 1 to 20 carbon atoms, an unsubstituted aryloxy group having from 6 to 30 carbon atoms, an unsubstituted alkenyl group having from 2 to 20 carbon atoms, an unsubstituted aryl group having from 6 to 30 carbon atoms or, preferably, an unsubstituted aryl group having from 6 to 12 carbon atoms, an unsubstituted heteroaryl group having from 3 to 30 carbon atoms or, preferably, an unsubstituted heteroaryl group having from 3 to 12 carbon atoms, an unsubstituted alkylsilyl group having from 3 to 20 carbon atoms, an unsubstituted arylsilyl group having from 6 to 20 carbon atoms, an unsubstituted amino group having from 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, ester, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof.
It will be understood that when a molecular fragment is described as a substituent or otherwise attached to another moiety, its name may be written depending on whether it is a fragment (e.g., phenyl, phenylene, naphthyl, dibenzofuranyl) or depending on whether it is an entire molecule (e.g., benzene, naphthalene, dibenzofuran). As used herein, these different ways of specifying substituents or linking fragments are considered to be equivalent.
In the compounds mentioned in the present disclosure, a hydrogen atom may be partially or completely replaced by deuterium. Other atoms such as carbon and nitrogen may also be replaced by their other stable isotopes. Substitution of other stable isotopes in the compounds may be preferred because it enhances the efficiency and stability of the device. In the compounds mentioned in the present disclosure, a deuterated substituent, such as deuterated methyl, means that at least one hydrogen atom in said substituent (methyl) is replaced by deuterium.
In the compounds mentioned in the present disclosure, multiple substitution means that a double substitution is included up to the range of the maximum available substitutions. When a substituent in a compound mentioned in the present disclosure represents multiple substitution (including di-substitution, tri-substitution, tetra-substitution, etc.), that is, it means that the substituent may exist at a plurality of available substitution positions on its connecting structure, and the substituent existing at each of the plurality of available substitution positions may be the same structure or different structures.
In the compounds mentioned in the present disclosure, adjacent substituents in the compounds cannot be linked to form a ring unless specifically defined, for example, adjacent substituents can be optionally linked to form a ring. In the compounds mentioned in the present disclosure, adjacent substituents can be optionally linked to form a ring, including both the case where adjacent substituents may be linked to form a ring and the case where adjacent substituents are not linked to form a ring. When adjacent substituents can optionally be joined to form a ring, the ring formed can be monocyclic or polycyclic, as well as alicyclic, heteroalicyclic, aromatic or heteroaromatic rings. In this expression, adjacent substituents may refer to substituents bonded to the same atom, substituents bonded to carbon atoms directly bonded to each other, or substituents bonded to carbon atoms further away. Preferably, adjacent substituents refer to substituents bonded to the same carbon atom as well as substituents bonded to carbon atoms directly bonded to each other.
The expression that two adjacent substituents can optionally be linked to form a ring is also intended to mean that two substituents bonded to the same carbon atom are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
the expression that two adjacent substituents can optionally be linked to form a ring is also intended to mean that two substituents bonded to carbon atoms directly bonded to each other are linked to each other by a chemical bond to form a ring, which can be exemplified by the following formula:
further, the expression that two adjacent substituents can be optionally connected to form a ring is also intended to be taken to mean that, in the case where one of the two substituents bonded to the carbon atom directly bonded to each other represents hydrogen, the second substituent is bonded at the position to which the hydrogen atom is bonded, thereby forming a ring. This is exemplified by the following equation:
according to one embodiment of the present invention, a compound having the structure of formula 1 is disclosed:
wherein, in the formula 1,
substituent R1-R10At least one of which has the structure of formula 2:
and the substituent R1-R10The remaining of (a) are, identically or differently on each occurrence, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstitutedSubstituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
wherein, in the formula 2,
l is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 60 carbon atoms, or a combination thereof;
X1-X3selected from CR, identically or differently at each occurrencexOr N;
Y1and Y5Selected from CR, identically or differently at each occurrencey1Or N;
Y2-Y4selected from CR, identically or differently at each occurrencey2、CRy3Or N, and Y2-Y4At least one of which is CRy2；
Z is selected, identically or differently on each occurrence, from C (R)z)2，NRzO, S or Se;
Rx、Ry3and RzEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstitutedAn arylsilyl group having 6 to 20 carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
Ry1each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, and combinations thereof;
Ry2each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;
adjacent substituents Rx、Ry1、Ry3Can optionally be linked to form a ring;
substituent RzCan optionally be linked to form a ring;
and represents the position of the substituent with the structure of the formula 2 connected with the formula 1.
In this example, the substituent R in formula 11To R10At least one of them has a structure represented by formula 2, and R1To R10The remainder of (a) are selected, identically or differently on each occurrence, from the group consisting of the substituents mentioned above. For example, when the substituent R1Having a structure represented by formula 2, then R1To R10The remainder of (1), namely R2To R10Each occurrence is selected, identically or differently, from the group consisting of the substituents mentioned above. When the substituent R is1And R6Having a structure represented by formula 2, then R1To R10The remainder of (1), namely R2To R5And R7To R10Each occurrence is selected, identically or differently, from the group consisting of the substituents mentioned above.
In this embodiment, the adjacent substituents Rx、Ry1、Ry3The optional attachment to form a ring includes the following: one case is when X1-X3A plurality of them are selected from CRxWhen adjacent to RxCan be connected to form a ring,for example X1And X2Selected from the group consisting of CRxWhen adjacent to RxMay be linked to form a ring; x1And X3Selected from the group consisting of CRxWhen adjacent to RxMay be linked to form a ring; x2And X3Selected from the group consisting of CRxWhen adjacent to RxMay be joined to form a ring. When Y is1And Y5Selected from the group consisting of CRy1，Y2-Y4A plurality of them are selected from CRy3When adjacent substituent Ry3May be linked to form a ring and/or an adjacent substituent Ry1And Ry3May be linked to form a ring, e.g. Y2And Y3Are all selected from CRy3When two R are presenty3May be linked to form a ring; y is3And Y4Are all selected from CRy3When two R are presenty3May be linked to form a ring; y is1Selected from the group consisting of CRy1And Y is2Selected from the group consisting of CRy3At this time Ry1And Ry3May be linked to form a ring; y is5Selected from the group consisting of CRy1And Y is4Selected from the group consisting of CRy3At this time Ry1And Ry3May be joined to form a ring. In another case adjacent substituents Rx、Ry1、Ry3Are not connected to form a ring.
In this example, the "substituent R" iszOptionally joined to form a ring "may comprise any one or more of the following: in one case for the substituent RzIn which there is a connection to form a ring, e.g. when two or more R's are present simultaneouslyzWhen R is equal tozIn which there is a connection to form a ring, e.g. RzThe two are connected to form a ring to form a spiral ring or bridge ring structure. Another case is for the substituent RzMay not be connected to form a ring.
The compound disclosed by the invention is in the N-meta position or N-para position of one aryl group of the arylamine, namely Y in the formula 22-Y4At least one of the aryl groups is substituted by (hetero) aryl, and the device performance can be improved by applying the aryl group to an organic electroluminescent device; on the basis of which it is possible to further position the aryl group in the N-ortho position, i.e. Y in formula 2 according to the invention1And/or Y5And (cyclo) alkyl substitution is introduced, so that the device performance can be further improved. Y in the invention1And/or Y5When the material is unsubstituted or substituted by (cyclo) alkyl, the performance of the device is improved, and the evaporation temperature of the material is mild, relatively speaking, such as Y1And/or Y5Is substituted by (hetero) aryl, and the deposition temperature thereof becomes high, which is disadvantageous in thermal stability required for materials by industry.
According to one embodiment of the invention, wherein the substituent R1To R10At least two of which have the structure of formula 2.
According to one embodiment of the invention, wherein the substituent R1To R10Two of which have the structure of formula 2.
According to one embodiment of the invention, wherein the substituent R1And R6Has the structure of formula 2.
According to one embodiment of the invention, wherein the substituent R2，R4-R5，R7And R9-R10Is a hydrogen atom, a substituent R3And R8Each occurrence, identically or differently, is selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms.
According to one embodiment of the invention, wherein L, identically or differently at each occurrence, is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 30 carbon atoms, or a combination thereof.
According to one embodiment of the invention, wherein L, identically or differently at each occurrence, is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 12 carbon atoms, or a combination thereof.
According to one embodiment of the invention, wherein L is a single bond.
According to one embodiment of the present invention, wherein X1To X3Selected from CR, identically or differently at each occurrencex，Y1And Y5Identical in each occurrence orAre differently selected from CRy1，Y2-Y4Selected from CR, identically or differently at each occurrencey2And CRy3And Y is2-Y4At least one of which is CRy2；
RxAnd Ry3Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof, having from 0 to 20 carbon atoms;
Ry1each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, and combinations thereof;
Ry2each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;
adjacent substituents Rx、Ry1、Ry3Can optionally be linked to form a ring.
According to one embodiment of the invention, wherein RxEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted alkyl having 3 to 20 ring carbonsAn atomic cycloalkyl group, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, and combinations thereof.
According to one embodiment of the invention, wherein RxEach occurrence, identically or differently, is selected from hydrogen, deuterium, fluoro, methyl, ethyl, isopropyl, cyclopentyl, cyclohexyl, phenyl, methylphenyl, isopropylphenyl, or a combination thereof.
According to one embodiment of the present invention, wherein Y2-Y4Selected from CR, identically or differently at each occurrencey2And CRy3And Y is2-Y4At least one of which is CRy2The balance being CRy3。
In this embodiment, "Y2-Y4At least one of which is CRy2The balance being CRy3"includes the following cases: when Y is2-Y4One of them is CRy2When the other two are CRy3(ii) a When Y is2-Y4Two of them are CRy2When the remaining one is CRy3(ii) a Or Y2-Y4Are all CRy2. For example when Y2Is CRy2When it is, then Y3And Y4Is CRy3(ii) a When Y is3Is CRy2When it is, then Y2And Y4Is CRy3(ii) a When Y is4Is CRy2When it is, then Y1And Y3Is CRy3(ii) a When Y is2And Y4Is CRy2When it is, then Y3Is CRy3(ii) a When Y is3And Y4Is CRy2When it is, then Y2Is CRy3；Y2、Y3、Y4Are all CRy2。
According to one embodiment of the present invention, wherein Y2-Y4Selected from CR, identically or differently at each occurrencey2And CRy3And Y is2-Y4One of them is CRy2The balance being CRy3。
According to one embodiment of the invention, wherein Ry3Selected from hydrogen, identically or differently at each occurrence,deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted aryl groups having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 12 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 6 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 12 carbon atoms, and combinations thereof.
According to one embodiment of the invention, wherein Ry3Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, fluoro, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, trimethylsilyl, and combinations thereof.
According to one embodiment of the invention, wherein Ry2Each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 24 carbon atoms, or a combination thereof.
According to one embodiment of the invention, wherein Ry2Each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 18 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 18 carbon atoms, or a combination thereof.
According to one embodiment of the invention, wherein Ry2Each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms, or a combination thereof.
According to one embodiment of the invention, wherein Ry2Each occurrence identically or differently selected from phenyl, 2-methylphenyl, 2-ethylphenyl, 2-isopropylphenyl, 2-tert-butylphenyl, biphenyl, terphenyl, quaterphenyl, triphenylene, tetraphenylene, 2-naphthyl, phenanthrene, anthracene, indene, fluorene, indole, carbazole, benzofuran, dibenzofuran, benzothiole, dibenzothiaole, benzothiophene, dibenzothiophene, dibenzoselenophene, deuterated 2-methylphenyl, deuterated 2-ethylphenyl, deuterated 2-isopropylphenyl,deuterated 2-tert-butylphenyl, or a combination thereof.
According to one embodiment of the present invention, wherein Y1And Y5Selected from CR, identically or differently at each occurrencey1And said R isy1Each occurrence, identically or differently, is selected from a substituted or unsubstituted alkyl group having 1 to 12 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 12 ring carbon atoms, or a combination thereof.
According to one embodiment of the present invention, wherein Y1And Y5Selected from CR, identically or differently at each occurrencey1And said R isy1Each occurrence, identically or differently, is selected from a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 6 ring carbon atoms, or a combination thereof.
According to one embodiment of the present invention, wherein Y1And Y5Selected from CR, identically or differently at each occurrencey1And said R isy1Each occurrence, identically or differently, is selected from hydrogen, deuterium, fluorine, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, neopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated n-propyl, deuterated isopropyl, deuterated cyclopropyl, deuterated n-butyl, deuterated isobutyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated neopentyl, deuterated cyclohexyl, or a combination thereof.
According to one embodiment of the invention, wherein Z is C (R)z)2And said R iszEach occurrence, the same or different, is selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, or combinations thereof.
According to one embodiment of the invention, wherein RzEach occurrence, identically or differently, is selected from the group consisting of hydrogen, halogen, deuterium, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butylButyl, cyclopentyl, cyclohexyl, or combinations thereof.
According to one embodiment of the invention, wherein Rx、Ry1And Ry3At least one of which is fluorine.
According to one embodiment of the present invention, wherein the compound is selected from the group consisting of compound BD1 through compound BD1267, the specific structures of compound BD1 through compound BD1267 are shown in claim 13.
According to an embodiment of the present invention, there is also disclosed an electroluminescent device including:
an anode, a cathode, a anode and a cathode,
a cathode electrode, which is provided with a cathode,
and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound having formula 1:
wherein, in the formula 1,
substituent R1-R10At least one of which has the structure of formula 2:
and the substituent Rl-Rl0The remaining of (a) are, identically or differently on each occurrence, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atomsAlkylsilyl, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino groups having 0 to 20 carbon atoms, acyl groups, carbonyl groups, carboxylic acid groups, ester groups, cyano groups, isocyano groups, mercapto groups, sulfinyl groups, sulfonyl groups, phosphino groups, and combinations thereof;
wherein, in the formula 2,
l is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 60 carbon atoms, or a combination thereof;
X1-X3is CRxOr N;
Y1and Y5Selected from CR, identically or differently at each occurrencey1Or N;
Y2-Y4selected from CR, identically or differently at each occurrencey2、CRy3Or N, and Y2-Y4At least one of which is CRy2；
Z is selected, identically or differently on each occurrence, from C (R)z)2，NRzO, S or Se;
Rx、Ry3and RzEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof, having from 0 to 20 carbon atoms;
Ry1each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, and combinations thereof;
Ry2each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;
adjacent substituents Rx、Ry1、Ry3Can optionally be linked to form a ring;
substituent RzCan optionally be linked to form a ring;
and represents the position of the substituent with the structure of the formula 2 connected with the formula 1.
According to one embodiment of the present invention, wherein the organic layer in the organic electroluminescent device comprises a light emitting layer, wherein the light emitting layer comprises the compound having formula 1.
According to one embodiment of the present invention, wherein the light emitting layer further comprises a compound having formula 3:
wherein, in the formula 3,
Rg1to Rg8Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 20 carbon atoms-an alkylsilyl group of 20 carbon atoms, a substituted or unsubstituted arylsilyl group of 6 to 20 carbon atoms, a substituted or unsubstituted amino group of 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
Rg9and Rg10Each occurrence, identically or differently, is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms.
According to one embodiment of the invention, a compound formula is also disclosed, which comprises a compound with a structure shown in formula 1, wherein the specific structure of the compound is shown in any embodiment.
In combination with other materials
The materials described herein for use in particular layers in an organic light emitting device may be used in combination with various other materials present in the device. Combinations of these materials are described in detail in U.S. patent application Ser. No. 0132-0161 of U.S. 2016/0359122A1, the entire contents of which are incorporated herein by reference. The materials described or referenced therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.
Materials described herein as being useful for particular layers in an organic light emitting device can be used in combination with a variety of other materials present in the device. For example, the light emitting dopants disclosed herein may be used in conjunction with a variety of hosts, transport layers, barrier layers, injection layers, electrodes, and other layers that may be present. Combinations of these materials are described in detail in U.S. patent application Ser. No. US2015/0349273A1, paragraph 0080-0101, the entire contents of which are incorporated herein by reference. The materials described or referenced therein are non-limiting examples of materials that may be used in combination with the compounds disclosed herein, and one skilled in the art can readily review the literature to identify other materials that may be used in combination.
In the examples of material synthesis, all reactions were carried out under nitrogen unless otherwise stated. All reaction solvents were anhydrous and used as received from commercial sources. The synthesis product is subjected to structural validation and characterization using one or more equipment conventional in the art (including, but not limited to, Bruker's nuclear magnetic resonance apparatus, Shimadzu's liquid chromatograph-mass spectrometer, gas chromatograph-mass spectrometer, differential scanning calorimeter, Shanghai prism-based fluorescence spectrophotometer, Wuhan Corset's electrochemical workstation, Anhui Beidek's sublimator, etc.) in a manner well known to those skilled in the art. In an embodiment of the device, the device characteristics are also tested using equipment conventional in the art (including, but not limited to, an evaporator manufactured by Angstrom Engineering, an optical test system manufactured by Fushida, Suzhou, an ellipsometer manufactured by Beijing Mass., etc.) in a manner well known to those skilled in the art. Since the relevant contents of the above-mentioned device usage, testing method, etc. are known to those skilled in the art, the inherent data of the sample can be obtained with certainty and without being affected, and therefore, the relevant contents are not described in detail in this patent.
Materials synthesis example:
the preparation method of the compound of the present invention is not limited, and the following compounds are typically but not limited to, and the synthetic route and the preparation method thereof are as follows:
synthesis example 1: synthesis of Compound BD32
The first step is as follows:
LDA (100mL,200mmol) was placed in a 250mL three-necked flask, stirred under dry ice-ethanol for half an hour, methyl isobutyrate (23mL, 200mmol) was added, and stirring was continued for half an hour. 1-bromo-2- (bromomethyl) benzene (25g, 100mmol) was added and filtered through celite. After concentration, a crude product intermediate 1 is obtained and directly subjected to the next reaction.
The second step is that:
intermediate 1(27g, 100mmol) and potassium hydroxide (56g, 1mol) were mixed, 100mL of water and 10mL of methanol were added, and the mixture was heated to 100 ℃ for reaction until the TLC detection reaction was completed. Cooling, adding concentrated hydrochloric acid to adjust system pH to acidity after reaction returns to room temperature, extracting organic phase with ethyl acetate, combining organic phases, and concentrating.
Dissolve the above product (27g, 100mmol) in 200mL of dichloromethane, N2Bubbling, adding one drop of DMF, gradually adding oxalyl chloride (12.8mL, 120mmol) dropwise, after the system generates no more bubbles, moving the reaction to an ice bath, stirring for half an hour, adding aluminum trichloride (14.3g, 108mmol) in batches, and monitoring by TLC until the reaction is finished. Purification by column chromatography eluting with PE gave intermediate 2 as a white solid (22g,91.6mmol, 85% yield).
The third step:
intermediate 2(22g, 99mmol) was dissolved in 300mL of methanol, stirred in an ice-water bath for half an hour and NaBH was added in portions4After completion of the reaction, the reaction mixture was filtered through celite, and the filtrate was concentrated.
The product was dissolved in dichloromethane and Et was added3SiH (22.5g, 198mmol), stirred in an ice-water bath for half an hour, gradually added TFA (34g,297mmol) dropwise, concentrated, and purified by column chromatography to give intermediate 3 as a colorless oil (7.7g,34.4mmol, 35% yield).
The fourth step:
pd is added at room temperature under the protection of nitrogen2(dba3) (1g,1.1mmol), intermediate 3(5.1g, 22.7mmol), 4-methyl- [1,1' -biphenyl]3-amine (5g, 27.2mmol), BINAP (1.4g,2.2mmol) and tBuONa (4.7g, 49.6mmol) was added to xylene (100mL) and the system was heated to 90 deg.C for reaction overnight. After the reaction was completed, purification was performed by column chromatography to obtain intermediate 4(5.7g, 17.4mmol, yield 76%) as a white solid.
The fifth step:
under the protection of nitrogen at room temperature, 1, 6-dibromopyrene (2.6g, 7.2mmol), intermediate 4(5.7g, 17.4mmol), Pd (OAc)2(161mg，0.72mmol)，tBu3PH+BF4 -(406mg, 1.4mmol) and tBuONa (2.7g, 28.2mmol) were added to xylene (20mL) and the system was heated to 100 ℃ until the reaction was complete. And purified by column chromatography to give the compound BD32 as a yellow-green solid (1.2g, 1.41mmol, 20% yield). The product was identified as the target product with a molecular weight of 852.4.
Synthesis example 2: synthesis of Compound BD1141
First step of
2-bromo-4-iodo-1-methylbenzene (100g, 337mmol), phenylboronic acid (49g, 404mmol), Pd (PPh)3)4(7.8g，6.8mmol)，K2CO3(116g, 843mmol) was placed in a 1000mL three-necked flask, and 340mL of toluene, 110mL of THF, and H were added2O110 mL, replacement of N2. Heating to 78 ℃ for reaction. The reaction is carried out until the raw material is completely reacted, and column chromatography purification is carried out to obtain the intermediate 5(80g, 325mmol, 97% yield) as colorless oily liquid.
Second step of
Intermediate 5(81g, 329mmol), NBS (61g, 345mmol) was placed in a 2L two-necked flask and 1.3L acetonitrile was added to replace N2Heating ofThe reaction is stirred to 80 ℃. Benzoyl peroxide (8g, 33mmol) was added portionwise. The reaction was carried out until the starting material was completely reacted, and column chromatography purification was carried out to obtain intermediate 6(82g, 253mmol, yield 77%) as a white solid.
The third step
LDA (130mL, 260mmol) was placed in a 500mL three-necked flask, stirred under dry ice-ethanol for half an hour, methyl isobutyrate (30mL, 260mmol) was added, and stirring was continued for half an hour. Intermediate 6(48g, 148mmol) was added. The reaction is carried out until the raw materials completely react, and column chromatography purification is carried out to obtain the product, namely the intermediate 7(50g, 145mmol, 98% yield) which is light yellow oily matter.
The fourth step
Intermediate 7(78g, 227mmol), KOH (88g, 1.57mol) were mixed and H was added2O (230mL), methanol (23mL), was heated to 100 ℃ for reaction until the reaction was complete by TLC. After cooling and the reaction returned to room temperature, concentrated HCl was added to adjust the pH of the system to acidic and the precipitated white solid was filtered to give intermediate (71g, 227 mmol).
The intermediate (20g, 60mmol) was dissolved in 200mL of dichloromethane, and N was passed through the solution2Adding one drop of DMF, gradually adding oxalyl chloride (30mL, 60mmol) dropwise, after the system generates no more bubbles, moving the reaction to an ice water bath for stirring for half an hour, adding aluminum trichloride (8g, 60mmol) in batches, and monitoring by TLC until the reaction is finished. Filtered through celite and concentrated. Column chromatography gave intermediate 8 as a white solid (6g,18.8mmol, 31% yield).
The fifth step
Intermediate 8 (1)8g, 57mmol) in methanol (180mL), stirring for half an hour in an ice water bath, and adding NaBH in portions4After completion of the reaction, the reaction mixture was filtered through celite, and the filtrate was concentrated.
The product was dissolved in dichloromethane and Et was added3SiH (12.7g, 111mmol) was stirred in an ice water bath for half an hour, and TFA (18g, 155mmol) was gradually added dropwise to react until the starting material completely reacted, and column chromatography purification was performed to obtain intermediate 9(12g, 39.9mmol, yield 70%) as a colorless oil.
The sixth step
Pd is added at room temperature under the protection of nitrogen2(dba)3(910mg,0.99mmol), BINAP (1.18g,1.99mmol), intermediate 9(6g,19.9mmol), [1,1' -Biphenyl]-3-amine (5.5g, 30mmol) and tBuONa (3.8g,39.8mmol) were added to toluene (100mL) and the system was heated to 120 ℃ for 2 h. After the reaction was completed, purification was performed by column chromatography to obtain intermediate 10(6.7g,16.4mmol, 83% yield) as a colorless oil.
Seventh step
Under the protection of nitrogen at room temperature, 1, 6-dibromopyrene (2.2g,6.1mmol), intermediate 10(5.5g,14mmol), Pd (OAc)2(68mg，0.3mmol)，tBu3PH+BF4 -(174mg,0.6mmol) and tBuONa (1.3g,14mmol), xylene (30mL) was added and the system was heated to 95 ℃. After the reaction was completed, purification was performed by column chromatography to obtain BD1141(5g,5.1mmol, yield 84%) as a yellow-green solid. The product was identified as the target product with a molecular weight of 976.5.
Synthetic example 3: synthesis of Compound BD151
First step of
Under the protection of nitrogen at-78 ℃, adding the intermediate 11(50g, 139mmol) into a 1L single-neck bottle, adding THF (400mL), dropwise adding iPrMgCl (84mL,167mmol), dropwise adding pivalaldehyde (36g, 418mmol) after half an hour, and heating to room temperature after dropwise adding. The reaction system was quenched with ammonium chloride, extracted with DCM, and the solvent removed to give an intermediate. The intermediate was dissolved in DCM (1400mL) and the system was cooled to 0 deg.C and Et was added3SiH (24g, 213mmol), TFA (36g, 320mmol) was added dropwise half an hour later and the reaction was allowed to warm to room temperature. After the reaction was completed, purification was performed by column chromatography to obtain intermediate 12(36g, 118mmol, yield 85%) as a crude colorless oil.
Second step of
Pd (OAc) at room temperature under the protection of nitrogen2(0.5g, 2.2mmol), intermediate 3(10g, 44.2mmol), benzophenone imine (8.8g, 48.7mmol), dppf (2.4g,4.4mmol) and tBuONa (8.8g,88.4mmol) were added to a 250mL one-neck flask, o-xylene (100mL) was added and the system was heated to 90 ℃ for reaction overnight. The reaction solution was treated with basic alumina and MgSO4Filtration and washing with Tol removed the solvent to give the crude product which was crystallized from PE to give the intermediate. The intermediate was dissolved in THF (30mL), HCl (10mL) was added and the reaction was allowed to proceed overnight. After the reaction was completed, purification was performed by column chromatography to obtain intermediate 13(6.2g,38.5mmol, yield 87%) as a white solid.
The third step
Pd is added at room temperature under the protection of nitrogen2(dba)3(0.5g,0.55mmol), intermediate 12(4g, 13.2mmol), intermediate 13(2.6g,16.1mmol), BINAP (685mg,1.1mmol) and tBuONa (2.8g,29.1mmol) were added to xylene (100mL) and the system was heated to 90 ℃ for reaction overnight. After the reaction is finished, the white solid is obtained by column chromatography purificationIntermediate 14(4.5g, 11.7mmol, 88% yield).
The fourth step
Under the protection of nitrogen at room temperature, intermediate 14(4g, 10.4mmol), 1, 6-dibromopyrene (1.56g, 4.35mmol), Pd (OAc)2(63mg，0.28mmol)，tBu3PH+BF4 -(162mg, 0.56mmol) and tBuONa (3.2g,33mmol) were added to xylene (30mL) and the system was heated to 100 ℃ until the reaction was complete. After the completion of the reaction, purification was performed by column chromatography to obtain BD151 as a yellow-green solid compound (1.1g,1.14mmol, 26% yield). The product was identified as the target product with a molecular weight of 964.6.
Synthetic example 4: synthesis of Compound BD250
First step of
Palladium acetate (0.15g, 0.67mmol), BINAP (0.83g, 1.32mmol) was added to toluene (70.0mL) at room temperature under nitrogen. Introducing N into the solution2After 20 min, intermediate 3(5.0g, 22.12mmol), 5-fluoro- [1,1' -biphenyl, were added]-3-amine (4.3g,23.23mmol), sodium tert-butoxide (6.4g,66.37 mmol). Continuously introducing N2After 10 minutes, the system was heated to 110 ℃ for 4 hours. After the reaction was completed, purification was performed by column chromatography to obtain intermediate 15(3.8g,11.41mmol, yield 52%) as a pale yellow oil.
Second step of
At room temperature under the protection of nitrogen, palladium acetate (35mg,0.16mmol), tBu3PH+BF4 -(91mg, 0.32mmol) xylene (40.0mL) was added. Introducing N into the solution2The reaction time is 20 minutes and the reaction time is 20 minutes,1, 6-dibromopyrene (2g, 5.56mmol), intermediate 15(3.8g,11.41 mmol), sodium tert-butoxide (2.1g, 22.2mmol) were added successively. Continuously introducing N2After 10 minutes, the system was heated to 95 ℃ until the reaction was complete. After the reaction was completed, purification was performed by column chromatography to obtain BD250(4g, 4.64mmol, 84% yield) as a yellow solid. The product was identified as the target product with a molecular weight of 860.4.
Synthesis example 5: synthesis of Compound BD441
First step of
Under the protection of nitrogen at 0 ℃, 2-methyl-5-fluoronitrobenzene (200g, 1.29mol) is dissolved in sulfuric acid, NBS (252g, 1.42mol) is added in portions, and the mixture is warmed to room temperature for reaction. After the reaction was completed, purification was performed by column chromatography to obtain intermediate 16(220g, 936mmol, yield 72%) as a yellow liquid.
Second step of
Intermediate 16(50g, 213mmol), Fe (35g, 638mmol) and NH were added at room temperature4C1(1.1g, 21.3mmol) was charged into a 1L one-necked flask, EtOH (400mL), water (100mL) were added, and the system was heated to 90 ℃ for reaction. After the completion of the reaction, column chromatography was performed to obtain intermediate 17(41g, 200mmol, yield 94%) as a pale yellow liquid.
The third step
Pd (PPh) is added at room temperature under the protection of nitrogen3)4(3.4g, 3mmol), intermediate 17(31g, 151mmol), 2-methylphenylboronic acid (21g, 159mmol) and K2CO3(52g, 378mmol) was put into a 1L one-necked flask, toluene (400mL), EtOH (200mL), and water (100mL) were added, and the system was heated to 90 ℃ to reactOvernight. The system was heated to 90 ℃ and reacted overnight. After the reaction was completed, column chromatography was performed to obtain intermediate 18(27g, 125mmol, 83% yield) as a pale yellow solid.
The fourth step
Pd is added at room temperature under the protection of nitrogen2dba3(0.5g,0.55mmol), intermediate 18(5.7g, 26.5mmol), intermediate 3(5g,22mmol), BINAP (685mg,1.1mmol) and tBuONa (8.3g,86.9mmol) were added to a 250mL single vial, xylene (100mL) was added and the system was heated to 90 ℃ for reaction overnight. After the reaction was completed, column chromatography was performed to obtain intermediate 19(7.3g, 20.2mmol, 91% yield) as a white solid.
The fifth step
At room temperature under the protection of nitrogen, intermediate 19(7.3g, 20mmol), 1, 6-dibromopyrene (3g, 8.4mmol), Pd (OAc)2(63mg,0.28mmol)，tBu3PH+BF4 -(162mg, 0.56mmol) and tBuONa (3.2g,33mmol) were added to xylene (30mL) and the system was heated to 100 ℃ until the reaction was complete. After the reaction was completed, the product was separated by column chromatography to obtain BD441 as a yellow-green solid (1.2g, 1.30mmol, yield 15.4%). The product was identified as the target product and had a molecular weight of 916.5.
Synthetic example 6: synthesis of Compound BD1148
First step of
Pd is added at room temperature under the protection of nitrogen2(dba)3(9l0mg, 0.99mmol), BINAP (1.18g,1.99mmol), intermediate 9(6g,19.9mmol), 4-methyl- [1,1' -biphenyl]-3-amine (5.5g, 30mmol) and t-BuONa (b3.8g,39.8mmol) was added toluene (100mL) and the system was heated to 120 ℃ for 2 h. After the reaction was completed, purification was performed by column chromatography to obtain intermediate 20(6.7g, 16.4mmol, yield 82.7%) as a white solid.
Second step of
Under the protection of nitrogen at room temperature, 1, 6-dibromopyrene (2.38g, 6.6mmol), intermediate 6(6.2g, 15.2mmol), Pd (OAc)2(74mg,0.33mmol)，t-Bu3P·H+BF4 -(191mg,0.66mmol) and t-BuONa (1.46g,15.2mmol), xylene (33mL) was added and the system was heated to 95 ℃. After the reaction was completed, the product compound BD1148(6g,5.97mmol, yield 90%) was obtained by column chromatography purification. The product was identified as the target product with a molecular weight of 1004.5.
Synthetic example 7: synthesis of Compound BD257
First step of
Pd (PPh) is added at room temperature under the protection of nitrogen3)4(3.4g, 3mmol), intermediate 17(55g, 268mmol), phenylboronic acid (50g,282mmol) and K2CO3(92g, 670mmol) was added to a 1L one-necked flask, Tol (400mL), EtOH (200mL), water (100mL) was added, and the system was heated to 90 ℃ for reaction overnight. After the reaction was completed, intermediate 21(42g,208mmol, yield 77%) was obtained as a pale yellow solid by column chromatography.
Second step of
Pd is added at room temperature under the protection of nitrogen2(dba)3(0.5g,0.55mmol), intermediate 21(5.4g, 26.2mmol), intermediate 3(5g,22mmol), BINAP (685mg,1.1mmol) and tBuONa (8.3g,86.9mmol) was added to a 250mL single neck flask, xylene (100mL) was added and the system was heated to 90 ℃ and reacted overnight. After the reaction was completed, column chromatography was performed to obtain intermediate 22(5.8g,16.7mmol, yield 76%) as a white solid.
The third step
Under the protection of nitrogen at room temperature, intermediate 22(5.8g,16.7mmol), 1, 6-dibromopyrene (2.5g,7.0mmol), Pd (OAc)2(63mg,0.28mmol)，tBu3PH+BF4 -(162mg, 0.56mmol) and tBuONa (3.2g,33mmol) were added to a 100mL single neck flask, xylene (30mL) was added and the system was heated to 100 ℃ until the reaction was complete. After completion of the reaction, the compound BD257 was obtained as a yellow-green solid (1.4g,1.57mmol, 22% yield) by column chromatography. The product was identified as the target product with a molecular weight of 888.4.
Synthesis example 8: synthesis of Compound BD261
First step of
1-bromo-2-fluoro-4-methylbenzene (94.5g, 0.5mol) was dissolved in 1L of concentrated sulfuric acid at 0 ℃ and concentrated nitric acid (37.8g,0.6mol) was slowly added dropwise. The reaction was allowed to warm to room temperature and stirred overnight. After completion of the reaction, a large amount of ice was added, followed by extraction with dichloromethane three times, and the organic phases were combined and separated by column chromatography to give intermediate 23(93.6g,0.4mol, yield 80%).
Second step of
Under nitrogen protection, intermediate 23(26.8g, 114.6mmol), phenylboronic acid (21g,172mmol), tetrakis (triphenylphosphine) palladium (6.7g, 5.74mmol), K were added to a dry 1L three-necked flask2CO3(47.5g,344mmol), toluene (240mL) and water (60mL) were purged with nitrogen three times, warmed to 100 ℃ overnight, the reaction was stopped, and separated by column chromatography to give intermediate 24(23.1g,100mmol, 89% yield).
The third step
Intermediate 24(23.1g,100 mmol) was dissolved in 1L of ethanol, and 100mL of saturated aqueous ammonium chloride was added. After addition of reduced iron powder (16.8g, 300mmol), the reaction was warmed to 80 ℃ and stirred for 3 hours. After cooling to room temperature, the reaction solution was filtered through celite, after evaporating off most of the ethanol, water was added, extraction was carried out three times with dichloromethane, and the organic phases were combined. Purification by column chromatography gave intermediate 25(19g, 95mmol, 95% yield).
The fourth step
Pd is added at room temperature under the protection of nitrogen2(dba)3(910mg,0.99mmol), BINAP (1.18g,1.99mmol), intermediate 25(6.03g, 30mmol), intermediate 3(4.48g,19.9mmol), and tBuONa (3.8g,39.8mmol) were added to toluene (200mL) and the system was heated to 120 ℃ for 2 h. After the reaction was completed, purification was performed by column chromatography to obtain intermediate 26(5.52g,16mmol, 53% yield) as a colorless oil.
The fifth step
Under the protection of nitrogen at room temperature, 1, 6-dibromopyrene (2.2g,6.1mmol), intermediate 26(5.52g,16 mmol), Pd (OAc)2(68mg,0.3mmol)，tBu3PH+BF4 -(174mg,0.6mmol) and t-BuONa (1.3g,14mmol), xylene (30mL) was added and the system was heated to 95 ℃. After the reaction is finishedPurification by column chromatography gave BD261 as a yellow-green solid (2g, 2.25mmol, 37% yield). The product was identified as the target product with a molecular weight of 888.4.
Synthetic example 9: synthesis of Compound BD177
First step of
2-bromo-4-fluoro-1-methylbenzene (120g, 634.9mmol), benzoyl peroxide (8g33mmol) were added to acetonitrile (1.5L) at room temperature, NBS (124g, 698.4mmol) was added in portions, heated to 80 ℃ and stirred. Purification by column chromatography after completion of the reaction gave intermediate 27(136g,507.46mmol, 80% yield) as a white solid.
Second step of
LDA (2M, 380mmol) was added to tetrahydrofuran (300mL), stirred under dry ice-ethanol for half an hour, methyl isobutyrate (87mL, 761.19mmol) was added dropwise, and after stirring for another half an hour, intermediate 27(136.0g, 507.46mmol in THF 200mL) was added dropwise. After the reaction was complete, water was added and quenched, extracted with ethyl acetate, the organic phase was concentrated and dissolved in methanol (800ml), KOH (78g, 1402mmol in H) was added2O400 ml), heated to 40 ℃ to react, and purified by column chromatography after completion of the reaction to give intermediate 28(116g, 415.77mmol, 82% yield) as a pale yellow oil.
The third step
Under the protection of nitrogen at 0 ℃, dissolving the intermediate 28(116g, 415.77mmol) in 500mL dichloromethane, adding N, N-dimethylformamide (0.5mL), gradually dropwise adding thionyl chloride (32mL, 436.56mmol), reacting at 0 ℃ for 2h, concentrating, adding the concentrated system into 500mL dichloromethane, adding aluminum trichloride (55g, 415.77mmol) at 0 ℃, then returning to room temperature for reaction, adding water after the reaction is complete, quenching, and separating. The organic phase was concentrated and purified by column chromatography to give intermediate 29 as a clear oil (40.0g,155.64mmol, 37% yield).
The fourth step
Intermediate 29(55g, 214.0lmmol) was dissolved in 500mL of methanol at 0 deg.C under nitrogen, sodium borohydride (9.7g, 256.8mmol) was added in portions until the reaction was complete, the mixture was filtered through celite, and the filtrate was concentrated.
The above product was dissolved in dichloromethane, triethylsilane (62.0g, 470.0mmol) was added, stirred for half an hour in an ice water bath, trifluoroacetic acid (60ml,810.8mmol) was gradually added dropwise, reacted at room temperature for 72h and concentrated, and purified by column chromatography to give intermediate 30(7.0g,28.92mmol, 14% yield) as a pale yellow oil.
The fifth step
Palladium acetate (148.0mg, 0.67mmol), BINAP (826.0mg, 1.32mmol), 4-methyl- [1,1' -biphenyl ] -3-amine (4.3g,23.23mmol), intermediate 30(5.0g,22.12mmol) and sodium tert-butoxide (6.4g,66.37mmol) were added to a 250mL one-neck flask under nitrogen at room temperature, toluene (100mL) was added, and the system was heated to 120 ℃ for 2 h. After the reaction was completed, purification was performed by column chromatography to obtain intermediate 31(3.8g,11.41mmol, yield 52%) as a pale yellow oil.
The sixth step
At room temperature under the protection of nitrogen, palladium acetate (35mg,0.16mmol), tBu3PH+BF4 -(91mg, 0.32mmol) and dimethyl ether was addedBenzene (40.0 mL). Introducing N into the solution2After 20 min, 1, 6-dibromopyrene (2.0g, 5.56mmol), intermediate 31(3.8g,11.41 mmol), sodium tert-butoxide (2.1g, 22.2mmol) were added successively. Continuously introducing N2For 10 minutes, the system was heated to 95 ℃. After the reaction was completed, purification was performed by column chromatography to obtain BD177(2.0g, 2.25mmol, 40% yield) as a yellow-green solid compound. The product was identified as the target product with a molecular weight of 888.4.
Synthetic example 10: synthesis of Compound BD393
First step of
Pd is added at room temperature under the protection of nitrogen2(dba)3(910mg,0.99mmol), BINAP (1.18g,1.99mmol), intermediate 3(5g,22.7mmol), 2 '-4-methyl- [1,1' -biphenyl]-3-amine (5.4g, 27.2mmol) and tBuONa (4.3g,45 mmol) were added to toluene (100mL) and the system was heated to 120 ℃ for 2 h. After the reaction was completed, purification was performed by column chromatography to obtain intermediate 32(5.4g, 15.8mmol, yield 71%) as a colorless oil.
Second step of
Under the protection of nitrogen at room temperature, 1, 6-dibromopyrene (2g, 6.28mmol), intermediate 32(4.9g, 14.45mmol), Pd (OAc)2(70mg，0.31mmol)，tBu3PH+BF4 -(180mg, 0.62mmol) and tBuONa (1.38g, 14.45mmol), xylene (30mL) was added and the system was heated to 95 ℃. After the reaction was completed, purification was performed by column chromatography to obtain BD393(4g, 4.54mmol, yield 72%) as a yellow-green solid. The product was identified as the target product with a molecular weight of 880.5.
Synthetic example 11: synthesis of Compound BD103
First step of
Under nitrogen protection, 1-isopropyl-2-nitrobenzene (25g, 151.3mmol), TFA (500mL), and concentrated sulfuric acid (50mL) were added to a dry 1L single-neck flask, and after dissolution, NBS (27g, 151.3mmol) was added in portions, and the mixture was cooled to 0 ℃ to return to room temperature, and the reaction was completed overnight. Column chromatography gave intermediate 33(28g, 114.6mmol, 75.7% yield).
Second step of
Under nitrogen protection, a dry 1L three-necked flask was charged with intermediate 33(28g, 114.6mmol), phenylboronic acid (21g,172mmol), tetrakistriphenylphosphine palladium (6.7g, 5.74mmol), K2CO3(47.5g,344mmol), dioxane (240mL) and water (60mL) were replaced with nitrogen three times, the reaction was stopped after warming to 100 ℃ overnight, and the reaction was separated by column chromatography to give intermediate 34(25g, 102.8mmol, 89.6% yield).
The third step
Under nitrogen protection, a dry 1L three-neck flask was charged with intermediate 34(25g, 100mmol), hydrazine hydrate (6g), FeCl3(2.5g), activated carbon (2.5g), toluene (275mL) and ethanol (275 mL). The temperature is increased to 90 ℃ and the mixture is refluxed, hydrazine hydrate (6mL) is added every hour, TLC monitoring is carried out, 42mL of hydrazine hydrate is added in total, and the reaction is completed after 24 hours. Cool down, filter through celite, rinse with DCM, extract and concentrate. Column chromatography isolation gave the title product, intermediate 35(18g,84.5mmol, 84.5% yield).
The fourth step
Under the protection of nitrogen at room temperatureNext, Pd is added2(dba)3(910mg,0.99mmol), BINAP (1.18g,1.99mmol), intermediate 35(6.33g,30mmol), intermediate 3(4.48g,19.9mmol), and tBuONa (3.8g,39.8mmol) were added to toluene (200mL) and the system was heated to 120 ℃ for 2 h. After the reaction was completed, purification was performed by column chromatography to obtain intermediate 36(5.8g,16.4mmol, 83% yield) as a colorless oil.
The fifth step
Under the protection of nitrogen at room temperature, 1, 6-dibromopyrene (2.2g,6.1mmol), intermediate 36(5.8g,16.4mmol), Pd (OAc)2(68mg,0.3mmol)，tBu3PH+BF4 -(174mg,0.6mmol) and tBuONa (1.3g,14mmol), xylene (30mL) was added and the system was heated to 95 ℃. After the reaction was completed, purification was performed by column chromatography to obtain BD103 as a yellowish green solid (4.6g,5.1mmol, 84% yield). The product was identified as the target product with a molecular weight of 908.5.
Synthetic example 12: synthesis of Compound BD25
First step of
Dissolving 4-olfactory-1-indanone (100g, 57mmol) in methanol (180mL), stirring in an ice water bath for half an hour, and adding NaBH in portions4(22.8g,600mol) until the reaction was complete, celite was filtered and the filtrate was concentrated.
The product was dissolved in dichloromethane and Et was added3SiH (67.4g,592mmol) was stirred in an ice-water bath for half an hour, gradually added dropwise TFA (103g,888mmol) and reacted until the starting material was completely reacted, and purified by column chromatography to obtain intermediate 37(44g,225mmol, 47% yield) as a colorless oil.
Second step of
Pd is added at room temperature under the protection of nitrogen2(dba)3(910mg,0.99mmol), BINAP (1.18g,1.99mmol), intermediate 37(4g,20.5mmol), [1,1' -Biphenyl]-3-amine (4.5g,24.6mmol) and tBuONa (3.9g,41mmol) were added to toluene (100mL) and the system was heated to 120 ℃ for 2 h. After the reaction was completed, purification was performed by column chromatography to obtain intermediate 38(6.2g,20.15mmol, yield 98%) as a colorless oily substance.
The third step
Under the protection of nitrogen at room temperature, 1, 6-dibromopyrene (2.5g,7mmol), intermediate 38(5.5g,16.2mmol), Pd (OAc)2(78mg,0.35mmol)，tBu3PH+BF4 -(200mg,0.7mmol) and tBuONa (1.6g,16.2mmol), xylene (35mL) was added and the system was heated to 95 ℃. After the reaction was completed, purification was performed by column chromatography to obtain BD25(4g,5.1mmol, 69% yield) as a yellow-green solid. The product was identified as the target product with a molecular weight of 796.4.
Synthesis of comparative example 1: synthesis of comparative Compound A
The first step is as follows:
pd is added at room temperature under the protection of nitrogen2(dba3) (1g,1.1mmol), intermediate 3(5g,22.7mmol), 2-methylaniline (2.9g,27.2mmol), BINAP (1.4g,2.2mmol) and t-BuONa (4.3g,45.4mmol) were added to xylene (100mL) and the system was heated to 90 ℃ for reaction overnight. Purification by column chromatography after the reaction was complete gave intermediate 39(4g,17.4mmol, 76% yield) as a white solid.
Second step of
Under the protection of nitrogen at room temperature, 1, 6-dibromopyrene (2.5g,7.0mmol), intermediate 39(4g,16.2mmol), Pd (OAc)2(78mg,0.35mmol)，tBu3PH+BF4 -(200mg,0.7mmol) and t-BuONa (1.6g,16.2mmol) were added to xylene (35mL) and the system was heated to 95 ℃ until the reaction was complete. And purified by column chromatography to give compound a as a yellow-green solid (3.4g,4.86mmol, 69%). The product was identified as the target product with a molecular weight of 700.4.
Synthesis of comparative example 2: synthesis of comparative Compound B
The first step is as follows:
pd is added at room temperature under the protection of nitrogen2(dba)3(910mg,0.99mmol), BINAP (1.18g,1.99mmol), intermediate 9(6g,19.9mmol), aniline (2.79g,30mmol) and tBuONa (3.8g,39.8mmol), toluene (100mL) was added and the system was heated to 120 ℃ for 3 h. After the reaction was completed, purification was performed by column chromatography to obtain intermediate 40(5.3g,16.9mmol, yield 85%) as a colorless oil.
The second step is that:
1, 6-di-olpyrene (2.38g, 6.6mmo1), intermediate 40(4.76g, 15.2mmo1), Pd (OAc) under the protection of nitrogen at room temperature2(74mg,0.33mmol)，t-Bu3P·HBF4(191mg,0.66mmol) and t-BuONa (1.46g,15.2mmol) were added to xylene (30mL) and the system was heated to 95 ℃. After the reaction was completed, it was purified by column chromatography to obtain comparative compound B (4.68g,5.67mmol, 86%) as a yellowish green solid. The product was identified as the target product with a molecular weight of 824.4.
It will be appreciated by those skilled in the art that the above preparation method is only an illustrative example, and that those skilled in the art can modify it to obtain other structures of the compounds of the present invention.
Device example 1
First, a glass substrate, having an Indium Tin Oxide (ITO) anode 80nm thick, was cleaned and then treated with oxygen plasma and UV ozone. After treatment, the substrate was dried in a glove box to remove moisture. The substrate is then mounted on a substrate holder and loaded into a vacuum chamber. The organic layer specified below was in a vacuum of about 10 degrees-8In the case of torr, the evaporation was performed by thermal vacuum evaporation at a rate of 0.2 to 2 angstroms/second in turn on an ITO anode. Compound HI was used as Hole Injection Layer (HIL). The compound HT is used as a Hole Transport Layer (HTL). Compound EB was used as an Electron Blocking Layer (EBL). Then compound BD32 was doped in compound BH and co-evaporated to serve as the light emitting layer (EML). Compound HB was used as a Hole Blocking Layer (HBL). On the hole blocking layer, compound ET and 8-hydroxyquinoline-lithium (Liq) were co-evaporated as an Electron Transport Layer (ETL). Finally, 8-hydroxyquinoline-lithium (Liq) was evaporated to a thickness of 1nm as an electron injection layer, and 120nm of aluminum as a cathode. The device was then transferred back to the glove box and encapsulated with a glass lid and moisture absorber to complete the device.
Device example 2
Device example 2 was carried out in the same manner as in device example 1 except that the compound BD1141 was used in place of the compound BD32 in the light-emitting layer (EML).
Device example 3
Device example 3 was carried out in the same manner as in device example 1 except that the compound BD151 was used in place of the compound BD32 in the light-emitting layer (EML).
Device example 4
Device example 4 was carried out in the same manner as in device example 1 except that the compound BD1148 was used in place of the compound BD32 in the light-emitting layer (EML).
Device example 5
Device example 5 was carried out in the same manner as in device example 1 except that the compound BD250 was used in place of the compound BD32 in the light-emitting layer (EML).
Device example 6
Device example 6 was carried out in the same manner as in device example 1 except that the compound BD441 was used instead of the compound BD32 in the light-emitting layer (EML).
Device comparative example 1
Device comparative example 1 was conducted in the same manner as in device example 1 except that compound a was used in place of compound BD32 in the light-emitting layer (EML).
Device comparative example 2
Device comparative example 2 was conducted in the same manner as in device example 1 except that the compound B was used in place of the compound BD32 in the light emitting layer (EML).
The detailed structure and thickness of the device layer portions are shown in table 1. Wherein more than one layer of the materials used is obtained by doping different compounds in the stated weight ratios.
TABLE 1 device structures of device examples and comparative examples
The material structure used in the device is as follows:
IVL was measured for all the examples and comparative devices at different current densities and voltages, while the evaporation temperature was measured. At a constant current of 1000cd/m2Next, the External Quantum Efficiency (EQE), the maximum emission wavelength (. lamda.) was measuredmax) Full width at half maximum (FWHM) and CIE data.
TABLE 2 device data for example 1, example 2, comparative example 1 and comparative example 2
| Device numbering | CIE(x,y) | λmax(nm) | FWHM(nm) | EQE(％) |
| Example 1 | 0.135,0.117 | 461 | 29.7 | 9.11 |
| Example 2 | 0.133,0.129 | 463 | 30.5 | 9.02 |
| Comparative example 1 | 0.136,0.127 | 461 | 31.7 | 8.43 |
| Comparative example 2 | 0.133,0.133 | 463 | 30.5 | 8.65 |
Discussion:
device data for example 1, example 2, comparative example 1 and comparative example 2 are shown in table 2. Compared with comparative example 1, it can be seen that when one aryl group of the arylamine is biaryl, the EQE is improved by nearly 8.07% (9.11vs.8.43), the half-peak width is narrowed by 2nm (29.7nm vs.31.7nm), and the device performance is effectively improved.
In addition, the EQE of example 2 was improved by nearly 4.28% compared to comparative example 2, and the half-peak width and maximum emission wavelength were maintained. In example 2, it is seen that, when one aryl group of the aromatic amine is a biaryl group, the EQE can be improved and the blue emission performance can be effectively increased, as compared with comparative example 2.
Table 3 device data for example 3 and example 4
| Device numbering | CIE(x,y) | λmax(nm) | FWHM(nm) | EQE(％) |
| Example 3 | 0.133,0.120 | 462 | 28.5 | 9.48 |
| Example 4 | 0.135,0.118 | 461 | 29.7 | 9.12 |
Discussion:
device data for examples 3 and 4 are shown in table 3. In example 4, methyl is further introduced at the N-ortho position of the arylamine, compared with the N-ortho position of the arylamine in example 2 without substituent, the EQE is improved (9.12vs.9.02), the half-peak width is narrowed (29.7nm vs.30.5nm), and the maximum emission wavelength is also subjected to blue shift (461nm vs. 463nm). The result shows that on the basis that one aryl of the arylamine is biaryl, the blue luminescence property can be further improved by introducing alkyl substituent groups at the N-ortho position of the aryl.
The N-ortho position of the aromatic amine in example 3 further introduced neopentyl groups, and compared with the N-ortho position of the aromatic amine in example 1 introduced methyl groups, the addition of ortho substituents and the gradual increase of EQE (9.48vs.9.11) with the increase of molecular volume of ortho substituents, and the narrowing of half-peak width (28.5nm vs.29.7nm) were followed. Both EQE and half-peak width were improved compared to comparative example 1. The result shows that on the basis that the arylamine has a double structure of a benzo five-membered ring and a biaryl substituent, the blue luminescence property can be further improved by introducing the substituent at the N-ortho position, and the influence is increased along with the increase of the molecular volume of the N-ortho position substituent.
Table 4 device data for example 5 and example 6
| Device numbering | CIE(x,y) | λmax(nm) | FWHM(nm) | EQE(％) |
| Example 5 | 0.139,0.089 | 456 | 31.3 | 8.99 |
| Example 6 | 0.140,0.089 | 455 | 29.4 | 8.71 |
Discussion:
device data for examples 5 and 6 are shown in table 3. Examples 5 and 6 introduce a fluorine substitution in the N-meta position of the arylamine aryl group and blue shift the maximum emission wavelengths by 7nm (456nm vs.463nm) and 6nm (455nm vs.461nm), respectively, compared to examples 2 and 1 without the fluorine substitution. The result shows that the introduction of fluorine substitution can enable the maximum emission wavelength to be blue-shifted on the basis of the double structure that the arylamine has the benzo five-membered ring and the biaryl substituent, so as to achieve the deep blue luminescence.
TABLE 5 deposition temperature of device examples inventive compounds
| Compound (I) | BD31 | BD151 | BD441 | BD250 |
| Deposition temperature/. degree.C | 228.5 | 230.0 | 236.0 | 209.0 |
The vapor deposition temperature data for the compounds of the present invention in the device examples are shown in Table 5, wherein the vapor deposition temperature is about 10 degrees of vacuum-8The torr material was vapor deposited at a rate of 0.04 angstroms/second. The compound disclosed by the invention improves the performance of the device, and meanwhile, the evaporation temperature of the material is mild, thereby being beneficial to the thermal stability required by the industry for the material.
In conclusion, in the aromatic amine substituted pyrene compound, one substituent of the aromatic amine is a substituted or unsubstituted ortho (hetero) aryl and penta (hetero) cyclic hydrocarbon structure, and the other is a substituted or unsubstituted bi (hetero) aryl, especially a substituted or unsubstituted biaryl not more than two aryl (phenyl) groups, and the novel compound obtained by combining the structure can realize a blue emission wavelength, a high EQE and a narrow half-peak width when being applied to an organic electroluminescent device, so that the comprehensive performance of the device is improved. Meanwhile, fluorine substitution or N-ortho substitution is introduced into the other (hetero) aryl group, so that the blue luminescence property can be further improved. The compound disclosed by the invention improves the performance of the device, and meanwhile, the evaporation temperature of the material is mild, thereby being beneficial to the thermal stability required by the industry for the material.
It should be understood that the various embodiments described herein are illustrative only and are not intended to limit the scope of the invention. Thus, the invention as claimed may include variations from the specific embodiments and preferred embodiments described herein, as will be apparent to those skilled in the art. Many of the materials and structures described herein may be substituted with other materials and structures without departing from the spirit of the present invention. It should be understood that various theories as to why the invention works are not intended to be limiting.
Claims (17)
1. A compound having the formula 1:
wherein, in the formula 1,
substituent R1-R10At least one of which has the structure of formula 2:
and the substituent R1-R10The remaining of (a) are, identically or differently on each occurrence, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof, having from 0 to 20 carbon atoms;
wherein, in the formula 2,
l is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 60 carbon atoms, or a combination thereof;
X1-X3selected from CR, identically or differently at each occurrencexOr N;
Y1and Y5Selected from CR, identically or differently at each occurrencey1Or N;
Y2-Y4selected from CR, identically or differently at each occurrencey2、CRy3Or N, and Y2-Y4At least one of which is CRy2；
Z is selected, identically or differently on each occurrence, from C (R)z)2，NRzO, S or Se;
Rx、Ry3and RzEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof, having from 0 to 20 carbon atoms;
Ry1each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, and combinations thereof;
Ry2each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;
adjacent substituents Rx、Ry1、Ry3Can optionally be linked to form a ring;
substituent RzCan optionally be linked to form a ring;
and represents the position of the substituent with the structure of the formula 2 connected with the formula 1.
2. The compound of claim 1, wherein substituent R1To R10At least two of which have the structure of formula 2; preferably, R1To R10Two of which have the structure of formula 2.
3. The compound of claim 2, wherein substituent R1And R6Has the structure of formula 2.
4. A compound according to claim 3, wherein the substituent R2，R4-R5，R7And R9-R10Is a hydrogen atom, a substituent R3And R8Each occurrence, identically or differently, is selected from hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 20 ring carbon atoms.
5. The compound of any one of claims 1-4, wherein L, identically or differently at each occurrence, is selected from a single bond, a substituted or unsubstituted arylene having 6 to 30 carbon atoms, a substituted or unsubstituted heteroarylene having 3 to 30 carbon atoms, or a combination thereof;
preferably, wherein L is a single bond.
6. The compound of any one of claims 1-5, wherein X1To X3Selected from CR, identically or differently at each occurrencex，Y1And Y5Selected from CR, identically or differently at each occurrencey1，Y2-Y4Selected from CR, identically or differently at each occurrencey2And CRy3And Y is2-Y4At least one of which is CRy2。
7. The compound of any one of claims 1-6, wherein RxEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, and combinations thereof;
preferably, said R isxEach occurrence, identically or differently, is selected from hydrogen, deuterium, fluoro, methyl, ethyl, isopropyl, cyclopentyl, cyclohexyl, phenyl, methylphenyl, isopropylphenyl, or a combination thereof.
8. The compound of any one of claims 1-7, wherein Y is2-Y4Selected from CR, identically or differently at each occurrencey2And CRy3And Y is2-Y4At least one of which is CRy2；
The R isy3Each occurrence identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted aryl groups having 6 to 12 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 12 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 6 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 12 carbon atoms, and combinations thereof;
preferably, wherein Ry3Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, fluoro, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, trimethylsilyl, and combinations thereof;
the R isy2Each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 24 carbon atoms, or a combination thereof;
preferably, said R isy2Each occurrence, the same or different, is selected from phenyl, 2-methylphenyl, 2-ethylphenyl, 2-isopropylphenyl, 2-tert-butylphenyl, biphenyl, terphenyl, quaterphenyl, triphenylene, tetraphenylene, 2-naphthyl, phenanthrene, anthracene, indene, fluorene, indole, carbazole, benzofuran, dibenzofuran, benzothiole, dibenzothiaole, benzothiophene, dibenzothiophene, dibenzoselenophene, or a combination thereof.
9. The compound of any one of claims 1-8, wherein Y is2-Y4Selected from CR, identically or differently at each occurrencey2And CRy3And Y is2-Y4One of them is CRy2The balance being CRy3；
The R isy3Each occurrence identically or differently selected from the group consisting of hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 6 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 6 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 6 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 12 carbon atoms, and combinations thereof;
preferably, wherein Ry3Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, fluoro, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, phenyl, trimethylsilyl, and combinations thereof;
the R isy2Each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 24 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 24 carbon atoms, or a combination thereof;
preferably, said R isy2Each occurrence being identical or different and is selected from the group consisting of phenyl, 2-methylphenyl, 2-ethylphenyl, 2-isopropylphenyl, 2-tert-butylphenyl, biphenyl, terphenyl, quaterphenyl, triphenylene, tetraphenylene, 2-naphthyl, phenanthrene, anthracene, indene, fluorene, indole, carbazole, benzofuran, dibenzofuran, benzothiole, bisbiphenylBenzothiole, benzothiophene, dibenzothiophene, dibenzoselenophene, deuterated 2-methylphenyl, deuterated 2-ethylphenyl, deuterated 2-isopropylphenyl, deuterated 2-tert-butylphenyl, or combinations thereof.
10. The compound of any one of claims 1-9, wherein Y is1And Y5Selected from CR, identically or differently at each occurrencey1And said R isy1Each occurrence, identically or differently, is selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 6 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 6 ring carbon atoms, or combinations thereof;
preferably, said R isy1Each occurrence, which may be the same or different, is selected from the group consisting of hydrogen, deuterium, fluorine, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, neopentyl, cyclohexyl, deuterated methyl, deuterated ethyl, deuterated n-propyl, deuterated isopropyl, deuterated cyclopropyl, deuterated n-butyl, deuterated isobutyl, deuterated tert-butyl, deuterated cyclopentyl, deuterated neopentyl, deuterated cyclohexyl, or a combination thereof.
11. The compound of any one of claims 1-10, wherein Z is C (R)z)2And said R iszEach occurrence identically or differently selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, or combinations thereof;
preferably, RzEach occurrence, identically or differently, is selected from hydrogen, halogen, deuterium, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl, isobutyl, tert-butyl, cyclopentyl, cyclohexyl, or a combination thereof;
substituent RzCan optionally be linked to form a ring.
12. The compound of any one of claims 1-11, wherein Rx、Ry1And Ry3At least one of which is fluorine.
13. The compound of claim 1, wherein the compound is selected from the group consisting of:
14. an electroluminescent device comprising:
an anode, a cathode, a anode and a cathode,
a cathode electrode, which is provided with a cathode,
and an organic layer disposed between the anode and the cathode, the organic layer comprising a compound having formula 1:
wherein, in the formula 1,
substituent R1-R10At least one of which has the structure of formula 2:
and the substituent R1-R10The remaining of (a) are, identically or differently on each occurrence, selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl having 3 to 20 carbon atoms, substituted or unsubstituted alkyl having 6 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 carbon atoms, or substituted or unsubstituted cycloalkyl having 3 to 20 carbon atomsAn arylsilyl group of carbon atoms, a substituted or unsubstituted amino group having 0 to 20 carbon atoms, an acyl group, a carbonyl group, a carboxylic acid group, an ester group, a cyano group, an isocyano group, a mercapto group, a sulfinyl group, a sulfonyl group, a phosphino group, and combinations thereof;
wherein, in the formula 2,
l is selected from a single bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, a substituted or unsubstituted heteroarylene group having 3 to 60 carbon atoms, or a combination thereof;
X1-X3is CRxOr N;
Y1and Y5Selected from CR, identically or differently at each occurrencey1Or N;
Y2-Y4selected from CR, identically or differently at each occurrencey2、CRy3Or N, and Y2-Y4At least one of which is CRy2；
Z is selected, identically or differently on each occurrence, from C (R)z)2，NRzO, S or Se;
Rx、Ry3and RzEach occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl groups having 2 to 20 carbon atoms, substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms, substituted or unsubstituted alkylsilyl groups having 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl groups having 6 to 20 carbon atoms, substituted or unsubstituted amino, acyl, carbonyl, carboxylic acid group, ester group, cyano, isocyano, mercapto, sulfinyl, sulfonyl, phosphino, and combinations thereof, having from 0 to 20 carbon atoms;
Ry1identical or different at each occurrenceIs selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl groups having 3 to 20 ring carbon atoms, and combinations thereof;
Ry2each occurrence, identically or differently, is selected from a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted heteroaryl group having 3 to 30 carbon atoms, or a combination thereof;
adjacent substituents Rx、Ry1、Ry3Can optionally be linked to form a ring;
substituent RzCan optionally be linked to form a ring;
and represents the position of the substituent with the structure of the formula 2 connected with the formula 1.
15. The organic electroluminescent device as claimed in claim 14, wherein the organic layer comprises a light emitting layer, wherein the light emitting layer comprises a compound having formula 1.
16. The organic electroluminescent device of claim 15, wherein the light emitting layer further comprises a compound having formula 3:
wherein, in the formula 3,
Rg1to Rg8Each occurrence, the same or different, is selected from the group consisting of: hydrogen, deuterium, halogen, substituted or unsubstituted alkyl having 1 to 20 carbon atoms, substituted or unsubstituted cycloalkyl having 3 to 20 ring carbon atoms, substituted or unsubstituted heteroalkyl having 1 to 20 carbon atoms, substituted or unsubstituted aralkyl having 7 to 30 carbon atoms, substituted or unsubstituted alkoxy having 1 to 20 carbon atoms, substituted or unsubstituted aryloxy having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl having 2 to 20 carbon atoms, substituted or unsubstituted aryl having 6 to 30 carbon atoms, substituted or unsubstituted aryl having 3 to 30 carbon atomsSubstituted or unsubstituted alkylsilyl group of 3 to 20 carbon atoms, substituted or unsubstituted arylsilyl group of 6 to 20 carbon atoms, substituted or unsubstituted amino group of 0 to 20 carbon atoms, acyl group, carbonyl group, carboxylic acid group, ester group, cyano group, isocyano group, mercapto group, sulfinyl group, sulfonyl group, phosphino group, and combinations thereof;
Rg9and Rg10Each occurrence, identically or differently, is selected from substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted heteroaryl groups having 3 to 30 carbon atoms.
17. A compound formulation comprising a compound of any one of claims 1-13.
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| US20110156016A1 (en) * | 2008-07-28 | 2011-06-30 | Masahiro Kawamura | Organic light-emitting medium and organic el element |
| JP2013118288A (en) * | 2011-12-02 | 2013-06-13 | Toyo Ink Sc Holdings Co Ltd | Material for organic electroluminescent device and application of the same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US20110156016A1 (en) * | 2008-07-28 | 2011-06-30 | Masahiro Kawamura | Organic light-emitting medium and organic el element |
| JP2013118288A (en) * | 2011-12-02 | 2013-06-13 | Toyo Ink Sc Holdings Co Ltd | Material for organic electroluminescent device and application of the same |
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