CN113045378A - Organic compound and application thereof - Google Patents
Organic compound and application thereof Download PDFInfo
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- CN113045378A CN113045378A CN201911387459.0A CN201911387459A CN113045378A CN 113045378 A CN113045378 A CN 113045378A CN 201911387459 A CN201911387459 A CN 201911387459A CN 113045378 A CN113045378 A CN 113045378A
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- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 23
- 239000000463 material Substances 0.000 claims abstract description 36
- 125000003118 aryl group Chemical group 0.000 claims abstract description 25
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims abstract description 4
- 125000000732 arylene group Chemical group 0.000 claims abstract description 4
- 125000005549 heteroarylene group Chemical group 0.000 claims abstract description 4
- 239000010410 layer Substances 0.000 claims description 64
- -1 nitro, hydroxyl Chemical group 0.000 claims description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 239000012044 organic layer Substances 0.000 claims description 6
- 125000001769 aryl amino group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052805 deuterium Inorganic materials 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 2
- 150000001616 biphenylenes Chemical group 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 description 59
- 238000006243 chemical reaction Methods 0.000 description 26
- 230000015572 biosynthetic process Effects 0.000 description 24
- 238000003786 synthesis reaction Methods 0.000 description 24
- 238000001704 evaporation Methods 0.000 description 18
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 230000008020 evaporation Effects 0.000 description 14
- 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 14
- 230000005525 hole transport Effects 0.000 description 13
- 238000004440 column chromatography Methods 0.000 description 12
- 238000001816 cooling Methods 0.000 description 12
- 238000002347 injection Methods 0.000 description 12
- 239000007924 injection Substances 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 239000010408 film Substances 0.000 description 9
- 239000011368 organic material Substances 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 230000000903 blocking effect Effects 0.000 description 7
- 238000005516 engineering process Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000002356 single layer Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 125000005577 anthracene group Chemical group 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 230000021615 conjugation Effects 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 4
- PIGVQJMWWHSAEZ-UHFFFAOYSA-N 9-bromo-10-(4-naphthalen-2-ylphenyl)anthracene Chemical compound C12=CC=CC=C2C(Br)=C(C=CC=C2)C2=C1C1=CC=C(C=2C=C3C=CC=CC3=CC=2)C=C1 PIGVQJMWWHSAEZ-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000010549 co-Evaporation Methods 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000008204 material by function Substances 0.000 description 3
- 229920000767 polyaniline Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000002390 rotary evaporation Methods 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- BMIBJCFFZPYJHF-UHFFFAOYSA-N 2-methoxy-5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine Chemical compound COC1=NC=C(C)C=C1B1OC(C)(C)C(C)(C)O1 BMIBJCFFZPYJHF-UHFFFAOYSA-N 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 2
- SYACRXBYRNYMLN-UHFFFAOYSA-N 9-bromo-10-naphthalen-1-ylanthracene Chemical compound C12=CC=CC=C2C(Br)=C(C=CC=C2)C2=C1C1=CC=CC2=CC=CC=C12 SYACRXBYRNYMLN-UHFFFAOYSA-N 0.000 description 2
- FKIFDWYMWOJKTQ-UHFFFAOYSA-N 9-bromo-10-naphthalen-2-ylanthracene Chemical compound C12=CC=CC=C2C(Br)=C(C=CC=C2)C2=C1C1=CC=C(C=CC=C2)C2=C1 FKIFDWYMWOJKTQ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000012295 chemical reaction liquid Substances 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000005401 electroluminescence Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 2
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 125000001725 pyrenyl group Chemical group 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 1
- PYLZAMJMDYIYIP-UHFFFAOYSA-N (2-amino-3-chlorophenyl)boronic acid Chemical compound NC1=C(Cl)C=CC=C1B(O)O PYLZAMJMDYIYIP-UHFFFAOYSA-N 0.000 description 1
- CAYQIZIAYYNFCS-UHFFFAOYSA-N (4-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1 CAYQIZIAYYNFCS-UHFFFAOYSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 1
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 1
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 description 1
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 description 1
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 1
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 1
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 description 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
- 125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 description 1
- 125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 description 1
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 description 1
- DLXBGTIGAIESIG-UHFFFAOYSA-N 1,8-dibromonaphthalene Chemical compound C1=CC(Br)=C2C(Br)=CC=CC2=C1 DLXBGTIGAIESIG-UHFFFAOYSA-N 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- MUCCHGOWMZTLHK-UHFFFAOYSA-N 2-nitronaphthalen-1-ol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=CC2=C1 MUCCHGOWMZTLHK-UHFFFAOYSA-N 0.000 description 1
- BGEVROQFKHXUQA-UHFFFAOYSA-N 71012-25-4 Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=C1C1=CC=CC=C1N2 BGEVROQFKHXUQA-UHFFFAOYSA-N 0.000 description 1
- BRUOAURMAFDGLP-UHFFFAOYSA-N 9,10-dibromoanthracene Chemical compound C1=CC=C2C(Br)=C(C=CC=C3)C3=C(Br)C2=C1 BRUOAURMAFDGLP-UHFFFAOYSA-N 0.000 description 1
- BVHHIMMHSQFJLR-UHFFFAOYSA-N 9-bromo-10-(3-phenylnaphthalen-1-yl)anthracene Chemical compound C12=CC=CC=C2C(Br)=C2C=CC=CC2=C1C(C1=CC=CC=C1C=1)=CC=1C1=CC=CC=C1 BVHHIMMHSQFJLR-UHFFFAOYSA-N 0.000 description 1
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 description 1
- 239000005964 Acibenzolar-S-methyl Substances 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- JTPHKHUWLNQSSU-UHFFFAOYSA-N C1=CC=CC=2C=CC=3C=4C=CC=CC4NC3C21.C2(=CC=CC1=CC=CC=C21)N2C1=CC=CC=C1C=1C=CC=CC21 Chemical compound C1=CC=CC=2C=CC=3C=4C=CC=CC4NC3C21.C2(=CC=CC1=CC=CC=C21)N2C1=CC=CC=C1C=1C=CC=CC21 JTPHKHUWLNQSSU-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L Cs2CO3 Substances [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- IVDFJHOHABJVEH-UHFFFAOYSA-N HOCMe2CMe2OH Natural products CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N Li2O Inorganic materials [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Inorganic materials [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 1
- LPTWEDZIPSKWDG-UHFFFAOYSA-N benzenesulfonic acid;dodecane Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCCCCCCCCCCC LPTWEDZIPSKWDG-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000006269 biphenyl-2-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(*)C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- UNXISIRQWPTTSN-UHFFFAOYSA-N boron;2,3-dimethylbutane-2,3-diol Chemical compound [B].[B].CC(C)(O)C(C)(C)O UNXISIRQWPTTSN-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229910052729 chemical element Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- 239000011162 core material Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 125000004987 dibenzofuryl group Chemical group C1(=CC=CC=2OC3=C(C21)C=CC=C3)* 0.000 description 1
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
- 229960005544 indolocarbazole Drugs 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000005990 isobenzothienyl group Chemical group 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000003933 pentacenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C12)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000011056 performance test Methods 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
- 239000003208 petroleum Substances 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 239000012414 tert-butyl nitrite Substances 0.000 description 1
- 125000005579 tetracene group Chemical group 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000007725 thermal activation Methods 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/62—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with more than three condensed rings
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/05—Isotopically modified compounds, e.g. labelled
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/52—Ortho- or ortho- and peri-condensed systems containing five condensed rings
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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- Engineering & Computer Science (AREA)
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- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
An organic compound having a structure represented by (I):
wherein m and n are each independently an integer of 0-10, and m + n is greater than or equal to 1 and less than or equal to 10; l is1And L2Each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene, or a substituted or unsubstituted C3-C30 heteroarylene; ar (Ar)1And Ar2Each independently selected from the group consisting of substituted and unsubstituted C6-C60 aryl, substituted and unsubstituted C3-C60 heteroaryl, and Ar1And Ar2At least one of them has a structure as shown in (II):
wherein A, B, C and D are each independently a substituted or unsubstituted aromatic ring bonded to L at either ring attachment position of A, B, C or D1Or L2And (4) connecting. When the organic compound is used as a luminescent main material in an organic electroluminescent device, the organic compound is beneficial to improving the efficiency of the device and reducing the driving voltage.
Description
Technical Field
The invention relates to the technical field of organic electroluminescence, in particular to an organic compound containing large conjugated condensed rings and application thereof.
Background
Organic Light Emission Diodes (OLED) devices are a kind of devices with sandwich-like structure, which includes positive and negative electrode films and Organic functional material layers sandwiched between the electrode films. And applying voltage to the electrodes of the OLED device, injecting positive charges from the positive electrode and injecting negative charges from the negative electrode, and transferring the positive charges and the negative charges in the organic layer under the action of an electric field to meet for composite luminescence. Because the OLED device has the advantages of high brightness, fast response, wide viewing angle, simple process, flexibility and the like, the OLED device is concerned in the field of novel display technology and novel illumination technology. At present, the technology is widely applied to display panels of products such as novel lighting lamps, smart phones and tablet computers, and further expands the application field of large-size display products such as televisions, and is a novel display technology with fast development and high technical requirements.
With the continuous advance of OLEDs in both lighting and display areas, much attention has been paid to the research on their core materials. This is because an efficient, long-lived OLED device is generally the result of an optimized configuration of the device structure and various organic materials, which provides great opportunities and challenges for chemists to design and develop functional materials with various structures. Common functionalized organic materials are: hole injection materials, hole transport materials, hole blocking materials, electron injection materials, electron transport materials, electron blocking materials, and light emitting host materials and light emitting objects (dyes), and the like.
In order to prepare an OLED light-emitting device with lower driving voltage, better light-emitting efficiency and longer service life, the performance of the OLED device is continuously improved, the structure and the manufacturing process of the OLED device need to be innovated, and photoelectric functional materials in the OLED device need to be continuously researched and innovated, so that functional materials with higher performance can be prepared. Based on this, the OLED material industry has been working on developing new organic electroluminescent materials to achieve low driving voltage, high luminous efficiency and better lifetime of the device.
Disclosure of Invention
Problems to be solved by the invention
In order to further satisfy the continuously improved requirements for the photoelectric properties of OLED devices and the energy saving requirements of mobile electronic devices, new and efficient OLED materials need to be continuously developed, wherein the development of new blue hosts with low driving voltage, high efficiency and long lifetime is of great significance.
Means for solving the problems
In order to solve the problems in the prior art, the inventors have intensively studied and found that anthracene is used as a matrix structure, a large conjugated group is introduced, so that molecules have good plane conjugation, the carrier transmission efficiency is improved, and secondly, the large conjugated group has a relatively high singlet state energy level and a low triplet state energy level, so that an organic electroluminescent device using a compound containing the group shows better efficiency and service life in a blue fluorescence system.
Specifically, the present invention provides an organic compound having a structure represented by (1):
wherein m and n are each independently an integer of 0 to 10, and 1. ltoreq. m + n. ltoreq.10, preferably 2. ltoreq. m + n. ltoreq.4, more preferably 2 or 3, most preferably 2; l is1And L2Each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene, or a substituted or unsubstituted C3-C30 heteroarylene; ar (Ar)1And Ar2Each independently selected from the group consisting of substituted and unsubstituted C6-C60 aryl, substituted and unsubstituted C3-C60 heteroaryl, and Ar1And Ar2At least one of them has a structure as shown in (II):
wherein A, B, C and D are each independently a substituted or unsubstituted aromatic ring at either of A, B, C or D ring positions connectable to L1Or L2Connecting; the above substituted or unsubstituted group has a substituentWhen the substituent is selected from deuterium, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C3-C10 cycloalkoxy, halogen, cyano, nitro, hydroxyl, silyl, amino, C6-C30 aryl, C6-C30 arylamino, C3-C30 heteroarylamino and C3-C30 heteroaryl, or a combination of two or more of them.
The specific reason why the compound of the general formula (I) of the present invention is excellent as a material for a light-emitting layer in an organic electroluminescent device is not clear, and it is presumed that the following reasons may be: the general formula compound of the invention introduces a structure of 7-membered conjugated aromatic rings on anthracene, has great conjugation, is beneficial to improving a singlet S1 energy level and reducing a triplet energy level T1, is beneficial to the transfer of current carriers in a blue fluorescent device, and has good rigidity due to the structure of the 7-membered conjugated aromatic rings, thereby having good stability and high glass transition temperature Tg. Combining the characteristics of the two aspects, the molecule can have good luminous efficiency and long service life.
In the present specification, the expression of Ca to Cb represents that the group has carbon atoms a to b, and the carbon atoms do not generally include the carbon atoms of the substituents unless otherwise specified. In the present invention, the expression of chemical elements includes the concept of chemically identical isotopes, such as the expression of "hydrogen", and also includes the concept of chemically identical "deuterium" and "tritium".
In the present specification, the expression of the loop structure marked by "-" indicates that the linking site is located at any position on the loop structure where the linking site can form a bond.
In the present specification, the definition of "aromatic ring" includes an aromatic ring, which is a hydrocarbon compound having a conjugated planar ring formed by alternating single and double bonds, and an aromatic heterocyclic ring, which is a compound having at least one heteroatom such as N, O, S in the conjugated planar ring, and the "aromatic ring" is preferably an aromatic ring.
In the present specification, the C6 to C60 aryl group is a group selected from the group consisting of phenyl, naphthyl, anthracenyl, benzanthracenyl, phenanthrenyl, benzophenanthrenyl, pyrenyl, grotto, perylenyl, fluoranthenyl, tetracenyl, pentacenyl, benzopyrenyl, biphenyl, idophenyl, terphenyl, quaterphenyl, fluorenyl, spirobifluorenyl, dihydrophenanthrenyl, dihydropyrenyl, tetrahydropyrenyl, cis-or trans-indenofluorenyl, triindenyl, isotridendenyl, spirotrimerization indenyl, and spiroisotridendenyl. Specifically, the biphenyl group is selected from 2-biphenyl, 3-biphenyl, and 4-biphenyl; terphenyl includes p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl and m-terphenyl-2-yl; the naphthyl group includes a 1-naphthyl group or a 2-naphthyl group; the anthracene group is selected from 1-anthracene group, 2-anthracene group and 9-anthracene group; the fluorenyl group is selected from the group consisting of 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl, and 9-fluorenyl; the pyrenyl group is selected from 1-pyrenyl, 2-pyrenyl and 4-pyrenyl; the tetracene group is selected from the group consisting of 1-tetracene, 2-tetracene, and 9-tetracene. The C6-C30 arylene group is similar to the C6-C60 aryl group, as long as the group satisfying the carbon number described above is changed to the corresponding subunit.
The heteroatom in the present invention generally refers to an atom or group of atoms selected from B, N, O, S, P, P (═ O), Si and Se, preferably selected from N, O, S. In the present specification, examples of the heteroaryl group having from C3 to C60 include: nitrogen-containing heteroaryl, oxygen-containing heteroaryl, sulfur-containing heteroaryl, and the like, and specific examples thereof include: furyl, thienyl, pyrrolyl, pyridyl, benzofuryl, benzothienyl, isobenzofuryl, isobenzothienyl, indolyl, isoindolyl, dibenzofuryl, dibenzothienyl, carbazolyl and derivatives thereof, quinolyl, isoquinolyl, acridinyl, phenanthridinyl, benzo-5, 6-quinolyl, benzo-6, 7-quinolyl, benzo-7, 8-quinolyl, phenothiazinyl, phenazinyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, naphthoimidazolyl, phenanthroimidazolyl, pyridoimidazolyl, pyrazinoimidazolyl, quinoxalimidazolyl, oxazolyl, benzoxazolyl, naphthooxazolyl, anthraoxazolyl, phenanthroizolyl, 1, 2-thiazolyl, 1, 3-thiazolyl, benzothiazolyl, pyridazinyl, benzpyridazinyl, Pyrimidinyl, benzopyrimidinyl, quinoxalinyl, 1, 5-diazananthracenyl, 2, 7-diazpyrenyl, 2, 3-diazpyrenyl, 1, 6-diazenyl, 1, 8-diazenyl, 4, 5, 9, 10-tetraazaperyl, pyrazinyl, phenazinyl, phenothiazinyl, naphthyridinyl, azacarbazolyl, benzocarbazinyl, phenanthrolinyl, 1, 2, 3-triazolyl, 1, 2, 4-triazolyl, benzotriazolyl, 1, 2, 3-oxadiazolyl, 1, 2, 4-oxadiazolyl, 1, 2, 5-oxadiazolyl, 1, 2, 3-thiadiazolyl, 1, 2, 4-thiadiazolyl, 1, 2, 5-thiadiazolyl, 1, 3, 4-thiadiazolyl, 1, 3, 5-triazinyl, 1, 2, 4-triazinyl, 1, 2, 3-triazinyl, tetrazolyl, 1, 2, 4, 5-tetrazinyl, 1, 2, 3, 4-tetrazinyl, 1, 2, 3, 5-tetrazinyl, purinyl, pteridinyl, indolizinyl, benzothiadiazole, etc., wherein the carbazolyl derivative is preferably 9-phenylcarbazole, 9-naphthylcarbazole benzocarbazole, dibenzocarbazole, or indolocarbazole. C3-C30 heteroarylene is similar to C3-C60 heteroaryl, provided that the above-mentioned group satisfying the carbon number is changed to the corresponding subunit.
In the present specification, the C1 to C10 chain alkyl group includes a straight-chain alkyl group and a branched-chain alkyl group, and specific examples thereof include: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, isopentyl, hexyl, heptyl, octyl, nonyl, decyl, preferably methyl. The C1-C10 chain alkoxy is similar to the C1-C10 chain alkyl, except that one-O-is correspondingly added to each group.
In the present specification, examples of the cycloalkyl group having from C3 to C10 include: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like, with cyclopropyl being preferred. C3-C10 cycloalkoxy and C3-C10 cycloalkyl, except that the groups are respectively and correspondingly added with one-O-.
In the present specification, examples of the halogen include: fluorine, chlorine, bromine, iodine, etc., preferably fluorine.
The above-mentioned compound of the general formula (I) of the present invention preferably has a structure represented by (I-1) or (I-2):
the reason why the above-mentioned preferred structure is more excellent as a material for a light-emitting layer is not clear, and it is presumed that the connection of a 7-membered conjugated aromatic ring or aromatic heterocyclic ring to a specific position of anthracene contributes to further increase of the singlet level S1 of the molecule, and further, such a large conjugated group has a good planar structure and contributes to the transport of carriers, so that the molecule has good photoelectric properties.
The compound of the above general formula of the present invention is preferably Ar1And Ar2At least one of them has a structure as shown in (II-1) or (II-2):
preferably Ar1And Ar2At least one of them has a structure as shown in (II-2-1) or (II-2-2):
wherein R is1And R2Each independently represents a single substituent up to the maximum allowable number of substituents, and each independently is any one selected from hydrogen, substituted or unsubstituted C1 to C10 chain alkyl groups, substituted or unsubstituted C3 to C10 cycloalkyl groups, substituted or unsubstituted C1 to C10 chain alkoxy groups, substituted or unsubstituted C3 to C10 cycloalkoxy groups, halogen, cyano groups, nitro groups, hydroxyl groups, silane groups, amino groups, and substituted or unsubstituted C6 to C30 aryl groups, substituted or unsubstituted C6 to C30 arylamino groups, substituted or unsubstituted C3 to C30 heteroarylamino groups, and substituted or unsubstituted C3 to C30 heteroaryl groups; and R is1And R2May be fused with the benzene ring to be bonded to form a ring, particularly when R is1Or R2When condensed with the attached benzene ring to form a ring, R1Or R2And only one benzene ring connected with the benzene ring is fused to form a ring, and a plurality of adjacent benzene rings are not fused to form a ring at the same time.
Preferred compounds of the above formula of the present invention are R1And R2Each is independentIs selected from any one of hydrogen, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C1-C10 chain alkyl and substituted or unsubstituted C3-C10 cycloalkyl, preferably R1And R2Each is hydrogen.
The compound of the above general formula of the present invention is preferably Ar1And Ar2One of them has the structure shown in (II), and the other is substituted or unsubstituted C6-C30 aryl.
The compound of the above formula of the present invention is preferably L1And L2Each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group, more preferably from a single bond or a substituted or unsubstituted phenylene group.
The compounds of the above general formula of the present invention are preferably selected from the structures represented by the following P1 to P136, but these compounds are representative only:
the organic compound provided by the invention is used in an organic electroluminescent device, so that the organic electroluminescent device has the effects of low starting voltage and high luminous efficiency.
The second purpose of the present invention is to provide an application of the organic compound in an organic electroluminescent device. The application may be, but is not limited to, a material used as a light emitting host in an organic electroluminescent device.
It is a further object of the present invention to provide an organic electroluminescent device comprising a first electrode, a second electrode and an organic layer between the first electrode and the second electrode, wherein the organic layer contains at least one of the above-mentioned organic compounds of the present invention. Preferably, the organic layer includes a light-emitting layer containing any one of the above organic compounds or a combination of at least two of the above organic compounds.
Effects of the invention
The general formula compound of the invention adopts a structure of 7-membered conjugated aromatic ring, and is mixed with benzene, naphthalene, phenanthrene, pyrene or the like commonly used in the prior art
Compared with the structure, the structure of the compound has larger conjugation, so that the compound has a higher singlet S1 energy level toAnd a lower triplet state energy level T1, which facilitates the transfer of carriers in the blue fluorescent device. Meanwhile, the compound contains a 7-membered conjugated aromatic ring with a large conjugated structure, so that the molecule has a good rigid structure, thereby having good stability and high glass transition temperature Tg. The structural characteristics of the two aspects can make the molecule show good luminous efficiency and long service life.
In addition, the preparation process of the compound is simple and feasible, the raw materials are easy to obtain, and the compound is suitable for mass production and amplification.
Detailed Description
The technical solutions of the present invention are further illustrated below by specific embodiments, and it should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as specifically limiting the present invention.
The basic chemical materials used in the following synthesis examples, such as ethyl acetate, sodium sulfate, toluene, tetrahydrofuran, dichloromethane, acetic acid, potassium carbonate, were purchased from Shanghai Tantake technology Co., Ltd and Xiong chemical Co., Ltd. Compounds of synthetic methods not described in the present invention are all starting products obtained commercially. The mass spectrometer used for determining the following compounds was a ZAB-HS type mass spectrometer measurement (manufactured by Micromass, UK).
The synthetic route of the compound of the general formula (I) is as follows:
synthesis of intermediate M1-M4:
1, 8-dibromonaphthalene (0.1mol, leq), phenylboronic acid (0.1mol, leq), potassium carbonate (0.2mol, 2eq), tetrakis (triphenylphosphine) palladium (0.001mol, 0.01eq), dioxane (300ml) and water (50ml) were added to a three-necked flask. The oil bath was heated to 90 ℃ for 6 hours and the reaction was monitored by TLC. The reaction solution was cooled to room temperature, and the solvent was removed by rotary evaporation under reduced pressure. And purifying the obtained crude product by column chromatography to obtain an intermediate M-A.
M-A (0.08mol, leq), pinacol o-aminobenzeneboronic acid ester (0.1mol, 1.2eq), potassium carbonate (0.12mol, 1.5eq), tetrakis (triphenylphosphine) palladium (0.0008mol, 0.01eq), dioxane (250ml) and water (40ml) were added to a three-necked flask. The oil bath was heated to 110 ℃ for 6 hours and the reaction was monitored by TLC. And cooling the reaction liquid to room temperature, and carrying out reduced pressure rotary evaporation to remove the solvent to obtain a crude product, and carrying out column chromatography purification to obtain an intermediate M-B.
Adding M-B (0.05mol) into 200ml of acetic acid, adding sulfuric acid (0.25mol), cooling to 10 ℃, dropwise adding an aqueous solution (0.1mol) of sodium nitrite, recovering the reaction at room temperature for 4 hours after dropwise adding, detecting by GC-MS to confirm that the reaction is complete, and purifying by column chromatography to obtain the intermediate M.
By replacing only the pinacol ester of orthoaminophenylboronic acid with the equivalent amount of the pinacol ester of chloroorthoaminophenylboronic acid according to the same method as described above, we can easily obtain the following intermediates:
synthesis of intermediate M5:
adding M (0.05mol) into 200ml of DMF, cooling to 0 ℃, dropwise adding a DMF solution (0.075mol) of NBS, recovering the reaction at room temperature for 4h after dropwise adding, detecting by GC-MS to confirm that the reaction is complete, and purifying by column chromatography to obtain an intermediate M5.
Synthesis of intermediate M6:
adding (0.1mol) 2-nitro-1-naphthol into 300ml dichloromethane, adding triethylamine (0.15mol), cooling to 0 ℃, dropwise adding 0.2mol trifluoromethanesulfonic anhydride, reacting at room temperature for 2h after dropwise addition, monitoring by TLC to complete reaction, slowly adding water to separate an organic phase, concentrating to obtain brown oily matter, and heating petroleum ether to obtain a yellow solid after boiling.
M6-A (0.1mol, leq), 2 '- (pinacolato-2-yl borate) - [1, 1' -biphenyl ] -2-amine (0.12mol, 1.2eq), potassium carbonate (0.15mol, 1.5eq), tetrakis (triphenylphosphine) palladium (0.001mol, 0.01eq), dioxane (250ml) and water (40ml) were added to a three-necked flask. The oil bath was heated to 110 ℃ for 6 hours and the reaction was monitored by TLC. And cooling the reaction liquid to room temperature, and carrying out reduced pressure rotary evaporation to remove the solvent to obtain a crude product, and carrying out column chromatography purification to obtain an intermediate M6-B.
M6-B (0.05mol, leq), sulfuric acid (0.1mol), acetic acid (200ml) was added to a three-necked flask. And (3) cooling to 10 ℃, dropwise adding a sodium nitrite aqueous solution (0.1mol), and after dropwise adding, reacting at room temperature for 2hTLC to monitor that the reaction is finished. Adding water and ethyl acetate for extraction, decompressing and rotary distilling to remove the solvent to obtain a crude product, and carrying out column chromatography purification to obtain an intermediate M6-C.
Adding M6-C (0.04mol, leq mol), iron powder (0.2mol) and ethanol (200ml) into a three-neck flask, heating and refluxing for reaction for 24 hours, directly spin-drying the ethanol after the reaction is completed, washing residues with dichloro, and concentrating an organic phase to obtain brown oil.
Adding M6-D (0.04mol), cuprous bromide (0.1mol) and hydrochloric acid (0.1mol) into 200ml of acetonitrile, cooling to 0 ℃, dropwise adding tert-butyl nitrite (0.1mol), reacting at 50 ℃ for 4 hours after dropwise adding, monitoring the reaction completion by GC-MS, and carrying out column chromatography to obtain an intermediate M6.
Synthetic examples
Synthesis example 1: synthesis of Compound P3
Adding M5(0.1mol, leq), pinacol diboron borate (0.12mol, 1.2eq), potassium acetate (0.15mol, 1.5eq), [1, 1' -bis (diphenylphosphino) ferrocene ] palladium dichloride (0.001mol, 1% eq) into a reaction bottle containing dioxane (300ml), heating and refluxing for 4h, directly filtering the reaction solution after the reaction is completed, concentrating, washing with methanol, and filtering to obtain an intermediate P3-A.
Adding P3-A (0.05mol), 9- (naphthalene-2-yl) -10-bromoanthracene (0.05mol), potassium carbonate (0.075mol), tetrakis (triphenylphosphine) palladium (0.0005mol, 0.0leq), dioxane (200ml) and water (30ml) into a reaction bottle, heating until reflux reaction is carried out for 5 hours and the reaction is complete, cooling, directly filtering, and carrying out column chromatography purification on a filter cake to obtain a compound P3.
Synthesis example 2: synthesis of Compound P7
In analogy to synthesis example 1, with the difference that 9- (naphthalen-2-yl) -10-bromoanthracene was replaced by an equivalent amount of 9-bromo-10- (4- (naphthalen-2-yl) phenyl) anthracene, compound P7 was obtained.
Synthesis example 3: synthesis of Compound P12
Adding P-chlorobenzeneboronic acid (0.1mol), 9- (naphthalene-1-yl) -10-bromoanthracene (0.1mol), potassium carbonate (0.12mol), tetrakis (triphenylphosphine) palladium (0.001mol, 0.01eq), dioxane (300ml) and water (50ml) into a reaction bottle, heating until reflux reaction is completed for 3 hours, cooling, adding 200ml of water and dichloromethane for extraction, concentrating an organic phase, and purifying by column chromatography to obtain a compound P12-A.
Adding P3-A (0.05mol), P12-A (0.05mol), potassium phosphate (0.075mol), tris (dibenzylideneacetone) dipalladium (0.0005mol, 0.01eq), 2-dicyclohexylphosphine-2 ', 6' -dimethoxy-biphenyl (0.1mol), dioxane (200ml) and water (30ml) into a reaction bottle, heating until the reflux reaction is completed for 8 hours, cooling, filtering, and purifying a filter cake by column chromatography to obtain a compound P12.
Synthesis example 4: synthesis of Compound P16
In analogy to Synthesis example 3, with the difference that 9- (naphthalen-1-yl) -10-bromoanthracene was replaced by an equivalent amount of 9-bromo-10- (3-phenylnaphthalen-1-yl) anthracene, compound P16 was obtained.
Synthesis example 5: synthesis of Compound P22
Adding P3-A (0.1mol), 9, 10-dibromoanthracene (0.05mol), potassium carbonate (0.12mol), tetrakis (triphenylphosphine) palladium (0.001mol, 0.01eq), dioxane (300ml) and water (50ml) into a reaction bottle, heating until reflux reaction is completed for 5h, cooling, adding 200ml water and dichloromethane for extraction, concentrating an organic phase, and purifying by column chromatography to obtain a compound P22.
Synthesis example 6: synthesis of Compound P39
Adding 2- (9, 10-di (naphthalene-2-yl) anthracene-2-yl) -boronic acid pinacol ester (0.05mol), M6(0.05mol), potassium carbonate (0.075mol), tetrakis (triphenylphosphine) palladium (0.0005mol, 0.01eq), dioxane (200ml) and water (30ml) into a reaction bottle, heating to reflux for 5h to react completely, cooling, adding 200ml water and dichloromethane for extraction, concentrating an organic phase, and purifying by column chromatography to obtain a compound P39.
Synthesis example 7: synthesis of Compound P56
In analogy to synthesis example 1, with the difference that 9-bromo-10- (4- (naphthalen-2-yl) phenyl) anthracene was replaced by an equivalent amount of 9-bromo-10- (4- (naphthalen-2-yl) pentadeuterated phenyl) anthracene, compound P56 was obtained.
Synthesis example 8: synthesis of Compound P97
In analogy to synthesis example 2, with the difference that 9-bromo-10- (4- (naphthalen-2-yl) phenyl) anthracene was replaced by an equivalent amount of 9-bromo-10- (4- (naphthalen-1-yl) pentadeuterated phenyl) anthracene and M5 was replaced by an equivalent amount of M3, compound P97 was obtained.
Device embodiments
The OLED includes first and second electrodes, and an organic material layer between the electrodes. The organic material may in turn be divided into a plurality of regions. For example, the organic material layer may include a hole transport region, a light emitting layer, and an electron transport region.
In a specific embodiment, a substrate may be used below the first electrode or above the second electrode. The substrate is a glass or polymer material having excellent mechanical strength, thermal stability, water resistance, and transparency. In addition, a Thin Film Transistor (TFT) may be provided on a substrate for a display.
The first electrode may be formed by sputtering or depositing a material used as the first electrode on the substrate. When the first electrode is used as an anode, an oxide transparent conductive material such as Indium Tin Oxide (ITO), Indium Zinc Oxide (IZO), tin dioxide (SnO2), zinc oxide (ZnO), or any combination thereof may be used. When the first electrode is used as a cathode, a metal or an alloy such as magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), or any combination thereof can be used.
The organic material layer may be formed on the electrode by vacuum thermal evaporation, spin coating, printing, or the like. The compound used as the organic material layer may be an organic small molecule, an organic large molecule, and a polymer, and a combination thereof.
The hole transport region is located between the anode and the light emitting layer. The hole transport region may be a Hole Transport Layer (HTL) of a single layer structure including a single layer containing only one compound and a single layer containing a plurality of compounds. The hole transport region may also be a multilayer structure including at least one of a Hole Injection Layer (HIL), a Hole Transport Layer (HTL), and an Electron Blocking Layer (EBL).
The material of the hole transport region may be selected from, but is not limited to, phthalocyanine derivatives such as CuPc, conductive polymers or polymers containing conductive dopants such as polyphenylenevinylene, polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (Pani/CSA), polyaniline/poly (4-styrenesulfonate) (Pani/PSS), aromatic amine derivatives such as compounds shown below in HT-1 to HT-34; or any combination thereof.
The hole injection layer is located between the anode and the hole transport layer. The hole injection layer may be a single compound material or a combination of a plurality of compounds. For example, the hole injection layer may employ one or more compounds of HT-1 to HT-34 described above, or one or more compounds of HI-1-HI-3 described below; one or more of the compounds HT-1 to HT-34 may also be used to dope one or more of the compounds HI-1-HI-3 described below.
The light-emitting layer includes a light-emitting dye (i.e., dopant) that can emit different wavelength spectra, and may also include a Host material (Host). The light emitting layer may be a single color light emitting layer emitting a single color of red, green, blue, or the like. The single color light emitting layers of a plurality of different colors may be arranged in a planar manner in accordance with a pixel pattern, or may be stacked to form a color light emitting layer. When the light emitting layers of different colors are stacked together, they may be spaced apart from each other or may be connected to each other. The light-emitting layer may be a single color light-emitting layer capable of emitting red, green, blue, or the like at the same time.
According to different technologies, the luminescent layer material can be different materials such as fluorescent electroluminescent material, phosphorescent electroluminescent material, thermal activation delayed fluorescent luminescent material, and the like. In an OLED device, a single light emitting technology may be used, or a combination of a plurality of different light emitting technologies may be used. These technically classified different luminescent materials may emit light of the same color or of different colors.
In one aspect of the invention, the light-emitting layer employs a fluorescent electroluminescence technique. The luminescent layer fluorescent dopant may be selected from, but is not limited to, combinations of one or more of BFD-1 through BFD-12 listed below.
The OLED organic material layer may further include an electron transport region between the light emitting layer and the cathode. The electron transport region may be an Electron Transport Layer (ETL) of a single-layer structure including a single-layer electron transport layer containing only one compound and a single-layer electron transport layer containing a plurality of compounds. The electron transport region may also be a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL).
The electron transport region may also be formed using the compound of the present invention for a multilayer structure including at least one of an Electron Injection Layer (EIL), an Electron Transport Layer (ETL), and a Hole Blocking Layer (HBL), although the material of the electron transport region may also be combined with one or more of ET-1 to ET-57 listed below.
The device may further comprise electrons between the electron transport layer and the cathodeInjection layer, electron injection layer materials including but not limited to, one or more of the following in combination: LiQ, LiF, NaCl, CsF, Li2O、Cs2CO3BaO, Na, Li and/or Ca.
The technical effects and advantages of the present invention are demonstrated and verified by testing practical use performance by specifically applying the compound of the present invention to an organic electroluminescent device.
Example 1
The embodiment provides a preparation method of an organic electroluminescent device, which comprises the following specific steps:
the glass plate coated with the ITO transparent conductive layer was sonicated in a commercial detergent, rinsed in deionized water, washed in acetone: ultrasonically removing oil in an ethanol mixed solvent, baking in a clean environment until the water is completely removed, cleaning by using ultraviolet light and ozone, and bombarding the surface by using low-energy cationic beams;
placing the glass substrate with the anode in a vacuum chamber, and vacuumizing until the pressure is less than 10-5Pa, performing vacuum evaporation on the anode layer film by using a multi-source co-evaporation method to obtain HI-3 serving as a hole injection layer, wherein the evaporation rate is 0.1nm/s, and the evaporation film thickness is 10 mm;
evaporating HT-4 on the hole injection layer in vacuum to serve as a first hole transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 40 nm;
evaporating HT-14 on the first hole transport layer in vacuum to serve as a second hole transport layer of the device, wherein the evaporation rate is 0.1nm/s, and the total evaporation film thickness is 10 nm;
a luminescent layer of the device is evaporated in vacuum on the second hole transport layer, the luminescent layer comprises a main material and a dye material, the evaporation rate of the main material P3 is adjusted to be 0.1nm/s by using a multi-source co-evaporation method, the evaporation rate of dye BFD-4 is set in a proportion of 5%, and the total film thickness of evaporation is 20 nm;
vacuum evaporating ET-17 on the luminescent layer to be used as a hole blocking layer of the device, wherein the evaporation rate is 0.1nm/s, and the total film thickness is 5 nm;
evaporating an electron transport layer on the hole blocking layer by using a multi-source co-evaporation method, adjusting the evaporation rate of a compound ET-46 to be 0.1nm/s, setting the evaporation rate to be 100% of the evaporation rate of ET-57, and setting the total film thickness of evaporation to be 23 nm;
LiF with the thickness of 1nm is vacuum-evaporated on the Electron Transport Layer (ETL) to be used as an electron injection layer, and an A1 layer with the thickness of 80nm is used as a cathode of the device.
Examples 2 to 8
Examples 2 to 8 were prepared in the same manner as in example 1 except that the compound P3 of the light-emitting layer was replaced with the compounds shown in table 1, respectively.
Comparative examples 1 to 2
Comparative examples 1-2 were prepared in the same manner as in example 1, except that the compound P3 of the light emitting layer was replaced with the existing compound C1 or C2, and the formula was:
the organic electroluminescent device prepared by the above process was subjected to the following performance measurement:
the driving voltage and current efficiency of the organic electroluminescent devices prepared in examples 1 to 8 and comparative examples 1 to 2 were measured at the same brightness using a Photo radiometer model PR 750 from Photo Research, a brightness meter model ST-86LA (photoelectric instrument factory, university of beijing), and a Keithley4200 test system. Specifically, the voltage was raised at a rate of 0.1V per second, and it was determined that the luminance of the organic electroluminescent device reached 1000cd/m2The current density is measured at the same time as the driving voltage; the ratio of the brightness to the current density is the current efficiency; the results of the performance tests are shown in table 1.
TABLE 1
As can be seen from table 1, under the condition that other materials in the organic electroluminescent device structure are the same, the organic electroluminescent devices provided in embodiments 1 to 8 of the present invention have higher current efficiency and lower driving voltage, wherein the current efficiency is 7.05 to 7.33cd/a, and the driving voltage is 4.11 to 4.22V.
The compounds C1 and C2 in the comparative examples are naphthalene-based anthracene substitutes, the driving voltages of the devices are 4.31V and 4.43V, the current efficiencies are 7.01cd/A and 6.31Vcd/A, and the performances are in a larger difference compared with the devices of the examples. The principle is not clear, but the reason is presumed as follows: the host materials of examples 1-8 employed 7-membered aromatic ring structures that were more conjugated than the comparative examples, and the overall degree of planar conjugation was much greater than the comparative examples, and therefore they had higher carrier transport capacity when combined with anthracene than the comparative examples. In addition, compared with the comparative example, the Tg of the compound of the invention is higher, which is beneficial to the thermal stability of the material.
The inventors have also found that although the device of example 6 has a lower driving voltage and higher current efficiency than those of comparative examples 1-2, none of the above parameters are comparable to those of the other examples. Example 6 differs from the other examples mainly in that the 7-membered aromatic ring of compound P39 of example 6 is not located at the 9 or 10 position of anthracene. Although the principle is not clear, it can be inferred that: the combination of the 7-membered aromatic ring and the 9-or 10-position of the specific position of anthracene is favorable for reducing the driving voltage and improving the current efficiency.
The experimental data show that the novel organic material is used as a fluorescent light-emitting layer of an organic electroluminescent device, is an organic light-emitting functional material with good performance, and has wide application prospect. It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.
Claims (10)
1. An organic compound having a structure represented by (I):
wherein m and n are each independently an integer of 0-10, and m + n is not less than 1 and not more than 10, preferably not less than 2 and not more than m + n and not more than 4;
L1and L2Each independently selected from a single bond, a substituted or unsubstituted C6-C30 arylene, or a substituted or unsubstituted C3-C30 heteroarylene;
Ar1and Ar2Each independently selected from the group consisting of substituted and unsubstituted C6-C60 aryl, substituted and unsubstituted C3-C60 heteroaryl, and Ar1And Ar2At least one of them has a structure as shown in (II):
wherein A, B, C and D are each independently a substituted or unsubstituted aromatic ring at either of A, B, C or D ring positions connectable to L1Or L2Connecting;
when the substituted or unsubstituted group has a substituent, the substituent is selected from any one of deuterium, C1-C10 alkyl, C3-C10 cycloalkyl, C1-C10 alkoxy, C3-C10 cycloalkoxy, halogen, cyano, nitro, hydroxyl, silyl, amino, C6-C30 aryl, C6-C30 arylamino, C3-C30 heteroarylamino, and C3-C30 heteroaryl, or a combination of at least two of them.
2. The organic compound according to claim 1, wherein the organic compound has a structure shown in (I-1), preferably a structure shown in (I-2):
3. the organic compound of claim 1 or 2, wherein Ar is Ar1And Ar2At least one of them has a structure as(II-1) or (II-2):
wherein R is1And R2Each independently represents a single substituent up to the maximum allowable number of substituents, and each independently is any one selected from hydrogen, substituted or unsubstituted C1 to C10 chain alkyl groups, substituted or unsubstituted C3 to C10 cycloalkyl groups, substituted or unsubstituted C1 to C10 chain alkoxy groups, substituted or unsubstituted C3 to C10 cycloalkoxy groups, halogen, cyano groups, nitro groups, hydroxyl groups, silane groups, amino groups, and substituted or unsubstituted C6 to C30 aryl groups, substituted or unsubstituted C6 to C30 arylamino groups, substituted or unsubstituted C3 to C30 heteroarylamino groups, and substituted or unsubstituted C3 to C30 heteroaryl groups; and R is1And R2May be fused with the attached benzene ring to form a ring.
4. The organic compound of claim 1 or 2, wherein Ar is Ar1And Ar2At least one of them has a structure as shown in (II-2-1) or (II-2-2):
wherein R is1And R2Each independently represents a single substituent to the maximum permissible substituent, and each independently is any one selected from the group consisting of hydrogen, substituted or unsubstituted C1 to C10 chain alkyl groups, substituted or unsubstituted C3 to C10 cycloalkyl groups, substituted or unsubstituted C1 to C10 chain alkoxy groups, substituted or unsubstituted C3 to C10 cycloalkoxy groups, halogen, cyano groups, nitro groups, hydroxyl groups, silyl groups, amino groups, and substituted or unsubstituted C6 to C30 aryl groups, substituted or unsubstituted C6 to C30 arylamino groups, substituted or unsubstituted C3 to C30 heteroarylamino groups, and substituted or unsubstituted C3 to C30 heteroaryl groups; and R is1And R2May be fused with the attached benzene ring to form a ring.
5. The organic compound of claim 3 or 4, wherein R is1And R2Each independently selected from any one of hydrogen, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted C1-C10 chain alkyl and substituted or unsubstituted C3-C10 cycloalkyl, preferably R1And R2Each is hydrogen.
6. The organic compound of any one of claims 1 to 4, wherein Ar is Ar1And Ar2One of them has the structure shown in (II), and the other is substituted or unsubstituted C6-C30 aryl.
7. The organic compound of claim 1 or 2, wherein L is1And L2Each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, or a substituted or unsubstituted biphenylene group.
8. The organic compound according to claim 1, having a structure represented by P1 to P136:
9. use of an organic compound according to any one of claims 1 to 8 in an organic electroluminescent device, preferably as a material for a light-emitting layer.
10. An organic electroluminescent device comprising a first electrode, a second electrode and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer contains at least one organic compound according to any one of claims 1 to 8.
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| CN109761981A (en) * | 2018-09-07 | 2019-05-17 | 北京拓彩光电科技有限公司 | Compound with anthracene nucleus and pyrido indole ring structures and the organic light emitting diode device containing the compound |
| CN112209802A (en) * | 2019-07-09 | 2021-01-12 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent compounds and organic electroluminescent device comprising the same |
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| CN109761981A (en) * | 2018-09-07 | 2019-05-17 | 北京拓彩光电科技有限公司 | Compound with anthracene nucleus and pyrido indole ring structures and the organic light emitting diode device containing the compound |
| CN112209802A (en) * | 2019-07-09 | 2021-01-12 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent compounds and organic electroluminescent device comprising the same |
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