TW201811719A - 化合物及其有機電子裝置 - Google Patents
化合物及其有機電子裝置 Download PDFInfo
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- TW201811719A TW201811719A TW106126649A TW106126649A TW201811719A TW 201811719 A TW201811719 A TW 201811719A TW 106126649 A TW106126649 A TW 106126649A TW 106126649 A TW106126649 A TW 106126649A TW 201811719 A TW201811719 A TW 201811719A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 56
- 125000003118 aryl group Chemical group 0.000 claims abstract description 31
- 239000010410 layer Substances 0.000 claims description 101
- 125000004432 carbon atom Chemical group C* 0.000 claims description 43
- 125000000524 functional group Chemical group 0.000 claims description 33
- 238000002347 injection Methods 0.000 claims description 29
- 239000007924 injection Substances 0.000 claims description 29
- 229910052805 deuterium Inorganic materials 0.000 claims description 21
- 125000004431 deuterium atom Chemical group 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 239000012044 organic layer Substances 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 239000000758 substrate Substances 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 14
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 230000005540 biological transmission Effects 0.000 claims description 9
- 230000000903 blocking effect Effects 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000002837 carbocyclic group Chemical group 0.000 claims description 7
- 230000005525 hole transport Effects 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000000707 boryl group Chemical group B* 0.000 claims description 6
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- KHNYNFUTFKJLDD-UHFFFAOYSA-N Benzo[j]fluoranthene Chemical group C1=CC(C=2C3=CC=CC=C3C=CC=22)=C3C2=CC=CC3=C1 KHNYNFUTFKJLDD-UHFFFAOYSA-N 0.000 claims description 4
- 150000001454 anthracenes Chemical group 0.000 claims description 4
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 4
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical class C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 claims description 3
- 150000002219 fluoranthenes Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 3
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- 239000012965 benzophenone Substances 0.000 claims description 2
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- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 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 claims description 2
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- SLGBZMMZGDRARJ-UHFFFAOYSA-N triphenylene Chemical class C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 230000004888 barrier function Effects 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims 1
- 229910052710 silicon Inorganic materials 0.000 claims 1
- 239000010703 silicon Substances 0.000 claims 1
- 125000004306 triazinyl group Chemical class 0.000 claims 1
- 125000003367 polycyclic group Chemical group 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 description 98
- 230000015572 biosynthetic process Effects 0.000 description 32
- 238000003786 synthesis reaction Methods 0.000 description 32
- 239000000463 material Substances 0.000 description 24
- 230000007246 mechanism Effects 0.000 description 23
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- 238000004458 analytical method Methods 0.000 description 15
- -1 1,3,5-tris (1-phenyl -1 H - benzimidazol-2-yl) phenyl Chemical group 0.000 description 14
- 239000000376 reactant Substances 0.000 description 14
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- 238000000434 field desorption mass spectrometry Methods 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 9
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- 239000011521 glass Substances 0.000 description 6
- 230000004048 modification Effects 0.000 description 6
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- 239000003446 ligand Substances 0.000 description 5
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000002619 bicyclic group Chemical group 0.000 description 4
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical group C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 3
- OIRHKGBNGGSCGS-UHFFFAOYSA-N 1-bromo-2-iodobenzene Chemical compound BrC1=CC=CC=C1I OIRHKGBNGGSCGS-UHFFFAOYSA-N 0.000 description 3
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- IVDFJHOHABJVEH-UHFFFAOYSA-N HOCMe2CMe2OH Natural products CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 150000001543 aryl boronic acids Chemical class 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
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- 230000000694 effects Effects 0.000 description 3
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- 229910052741 iridium Inorganic materials 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
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- 239000007858 starting material Substances 0.000 description 3
- RFDGVZHLJCKEPT-UHFFFAOYSA-N tris(2,4,6-trimethyl-3-pyridin-3-ylphenyl)borane Chemical compound CC1=C(B(C=2C(=C(C=3C=NC=CC=3)C(C)=CC=2C)C)C=2C(=C(C=3C=NC=CC=3)C(C)=CC=2C)C)C(C)=CC(C)=C1C1=CC=CN=C1 RFDGVZHLJCKEPT-UHFFFAOYSA-N 0.000 description 3
- RKVIAZWOECXCCM-UHFFFAOYSA-N 2-carbazol-9-yl-n,n-diphenylaniline Chemical compound C1=CC=CC=C1N(C=1C(=CC=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 RKVIAZWOECXCCM-UHFFFAOYSA-N 0.000 description 2
- WCXKTQVEKDHQIY-UHFFFAOYSA-N 3-[3-[3-(3,5-dipyridin-3-ylphenyl)phenyl]-5-pyridin-3-ylphenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=C(C=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=NC=CC=2)C=2C=NC=CC=2)=C1 WCXKTQVEKDHQIY-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
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- 238000005481 NMR spectroscopy Methods 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 2
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- 238000003756 stirring Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical class C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
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- 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 1
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- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- RWHRJJMRDNZTHU-UHFFFAOYSA-N 4-N-naphthalen-1-yl-4-N-[4-[4-[1-(naphthalen-1-ylamino)-4-(N-phenylanilino)cyclohexa-2,4-dien-1-yl]phenyl]phenyl]-1-N,1-N-diphenylbenzene-1,4-diamine Chemical compound C1(=CC=C(C=C1)C1(CC=C(C=C1)N(C1=CC=CC=C1)C1=CC=CC=C1)NC1=CC=CC2=CC=CC=C12)C1=CC=C(C=C1)N(C1=CC=C(C=C1)N(C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC2=CC=CC=C12 RWHRJJMRDNZTHU-UHFFFAOYSA-N 0.000 description 1
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- XZCJVWCMJYNSQO-UHFFFAOYSA-N butyl pbd Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)O1 XZCJVWCMJYNSQO-UHFFFAOYSA-N 0.000 description 1
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- 238000005259 measurement Methods 0.000 description 1
- ABCGFHPGHXSVKI-UHFFFAOYSA-O meso-tetrakis(n-methyl-4-pyridyl)porphine(4+) Chemical compound C1=C[N+](C)=CC=C1C(C1=CC=C(N1)C(C=1C=C[N+](C)=CC=1)=C1C=CC(=N1)C(C=1C=C[N+](C)=CC=1)=C1C=CC(N1)=C1C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 ABCGFHPGHXSVKI-UHFFFAOYSA-O 0.000 description 1
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- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
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- 235000011056 potassium acetate Nutrition 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- JSTHREDTMPIBEX-UHFFFAOYSA-N pyrene-2,7-diamine Chemical class C1=C(N)C=C2C=CC3=CC(N)=CC4=CC=C1C2=C43 JSTHREDTMPIBEX-UHFFFAOYSA-N 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
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
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Classifications
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- 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
- H10K85/625—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing at least one aromatic ring having 7 or more carbon atoms, e.g. azulene
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/002—Heterocyclic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
- C07C255/51—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings containing at least two cyano groups bound to the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/57—Nitriles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/18—Benzimidazoles; Hydrogenated benzimidazoles with aryl radicals directly attached in position 2
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/94—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
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- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
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- C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
- C07D333/80—Seven-membered rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
本發明是關於一種化合物及其有機電子裝置,該化合物可以式(I)表示:
式(I)中,X1和X2各自獨立為C(Ra),且該二Ra彼此相同或不同,該二Ra連接構成一芳香環;X3和X4各自獨立為C(Rb),且該二Rb彼此相同或不同,該二Rb連接構成一多芳香環。
Description
本發明是關於一種新穎化合物以及一種使用其之有機電子裝置,尤指一種用於電子傳輸層的新穎化合物以及使用其之有機電子裝置。
隨著科技的進步,各種使用有機材料製成的有機電子裝置蓬勃發展,常見的有機電子裝置如有機發光二極體(organic light emitting device,OLED)、有機光電晶體(organic phototransistor)、有機光伏打電池(organic photovoltaic cell)和有機光偵測器(organic photodetector)。
OLED最初是由伊士曼柯達公司(Eastman Kodak)所發明並提出,伊士曼柯達公司的鄧青雲博士和Steven Van Slyke以真空蒸鍍法(vacuum evaporation method)於形成有有機芳香二元胺電洞傳輸層的透明氧化銦錫(indium tin oxide,ITO)玻璃上沉積一電子傳輸材料{例如三(8-羥基喹啉)鋁[tris(8-hydroxyquinoline)aluminum(III),簡稱為Alq3]};再於電子傳輸層上沉積一金屬電極,即可完成OLED的製作。OLED因兼具反應速率快、質輕、薄形化、廣視角、亮度高、對比高、無需設置背光源以及低耗能的優點,因此備受關注,但OLED仍具有低效率和壽命短的問題。
為了克服低效率的問題,其中一種改善方式為於陰極和陽極間設置中間層,請參閱圖1所示,改良的OLED依序設置有一基板11、一陽極12、一電洞注入層13(hole injection layer,HIL)、一電洞傳輸層14(hole transport layer,HTL)、一發光層15(an emission layer,EL)、一電子傳輸層16(electron transport layer,ETL)、一電子注入層17(electron injection layer,EIL)和一陰極18。當於陽極12和陰極18施加一電壓時,由陽極12射出的電洞會穿過HIL和HTL並移動至EL,而由陰極18射出的電子會穿過EIL和ETL移動至EL,使電洞和電子在EL層重組成激子(exciton),當激子由激發態衰退返回基態時即可產生光線。
另一改善方式為改良OLED中ETL的材料,使電子傳輸材料展現出電洞阻擋能力,傳統的電子傳輸材料包括3,3'-[5'-[3-(3-吡啶基)苯基][1,1':3',1"-三聯苯]-3,3"-二基]聯吡啶{(3,3'-[5'-[3-(3-Pyridinyl)phenyl][1,1':3',1"-terphenyl]-3,3"-diyl]bispyridine,TmPyPb}、3-(4-聯苯基)-5-(4-叔丁基苯基)-4-苯基-4H-1,2,4-三嗪(3-(Biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole,TAZ)、1,3,5-三(1-苯基-1H-苯並咪唑-2-基)苯[1,3,5-tris(1-phenyl-1H-benzimidazol-2-yl)benzene,TPBi]、三(2,4,6-三甲基-3-(3-吡啶基)苯基)硼烷[tris(2,4,6-trimethyl-3-(pyridin-3-yl)phenyl)borane,3TPYMB]、1,3-聯(3,5-二吡啶-3-基-苯基)苯[1,3-bis(3,5-dipyrid-3-yl-phenyl)benzene,BmPyPb]和9,10-二(3-(3-吡啶基)苯基)蒽[9,10-bis(3-(pyridin-3-yl)phenyl)anthracene,DPyPA]。
然而,即使使用了所述電子傳輸材料,OLED的電流效率仍具有可改善的空間,因此,本發明提供了一種新穎的化合物以克服傳統低電流效率的問題。
本發明的目的為提供一種新穎化合物,其可用於有機電子裝置。
本發明的另一目的為提供一種使用該新穎化合物的有機電子裝置,藉此降低有機電子裝置之驅動電壓,並提升有機電子裝置的效率。
為達上述目的,本發明的新穎化合物可以式(I)表示:
於式(I)中,X1和X2各自獨立為C(Ra),且該二Ra彼此相同或不同,該二Ra連接構成一芳香環;於式(I)中,X3和X4各自獨立為C(Rb),且該二Rb彼此相同或不同,該二Rb連接構成一多芳香環;於式(I)中,Z1至Z10各自獨立選自於由下列所構成的群組:氫原子、氘原子、三氟甲基、鹵基、氰基、硝基、碳數為1至40的烷基、碳數為2至40的烯基、碳數為2至40的炔基、環上碳數為3至60的環烷基、環上碳數為3至60的雜環烷基、環上碳數為6至60的芳香基、環上碳數為3至60的雜芳基、碳數為1至40的烷氧基、環上碳數為6至60的芳氧基、碳數為1至40的矽烷基(alkylsilyl group)、環上碳數為6至60的芳矽基(arylsilyl group)、碳數為1至40的硼烷基(alkylboron)、環上碳數為6至60的芳硼基(arylboron group)、碳數為1至40的膦基(phosphine group)和碳數為1至40的氧膦基(phosphine oxide group)。
根據本發明,式(I)中自X3和X4延伸形成的該多芳香環包含至少二環狀芳香環彼此連接或並合,且該二環狀芳香環的環狀主結構是由碳原子所組成,即該二環狀芳香環不是雜芳環且不包含任何氮、氧或硫等 原子,然而,該二環狀芳香環可連接有任何取代基,該取代基可包含任何原子並不僅限於碳原子。
根據本發明,式(I)中X1和X2包含的雙鍵和該二C(Ra)連接形成的雙鍵互為共軛雙鍵(conjugated double bond),並構成前述的該芳香環;相同的,式(I)中X3和X4包含的雙鍵和該二C(Rb)連接形成的雙鍵互為共軛雙鍵,並構成前述的該多芳香環;根據本發明,自X1和X2延伸形成的該芳香環和自X3和X4延伸形成的該多芳香環彼此連接並合而成一包含至少六共軛雙鍵的芳香基;更佳的,自X1和X2延伸形成的該芳香環和自X3和X4延伸形成的該多芳香環彼此連接並合而成一包含至少八共軛雙鍵的芳香基。
式(I)中自X1和X2延伸形成的該芳香環可以是一經取代或未經取代且環上碳數為6至60的碳環,更佳的,自X1和X2延伸形成的該芳香環可以是一經取代或未經取代且環上碳數為6至20的碳環。舉例而言,該經取代或未經取代且環上碳數為6至60的碳環可以是一經取代或未經取代的苯環(benzene ring)、一經取代或未經取代的萘環(naphthalene ring)、一經取代或未經取代的蒽環(anthracene ring)、一經取代或未經取代的菲環(phenanthrene ring)、一經取代或未經取代的芴環(fluorene ring)、一經取代或未經取代的芘環(pyrene ring)、一經取代或未經取代的苯並菲(benzophenanthrene ring)、一經取代或未經取代的苯並芘(benzopyrene ring)、一經取代或未經取代的熒蒽環(fluoranthene ring)和一經取代或未經取代的苯並熒蒽環(benzofluoranthene ring),但不限於此。更佳的,該經取代或未經取代且碳數為6至60的碳環為一經取代或未經取代的苯環結構。前述環上碳數為6至60的碳環上的取代基可以是但不限於:氘原子、鹵基、氰基、硝基、碳數為1至12的烷基、碳數為2至12的烯基或碳數為2至12的炔基。
式(I)中自X3和X4延伸形成的該多芳香環可以是一經取代或 未經取代的萘環、一經取代或未經取代的蒽環、一經取代或未經取代的菲環、一經取代或未經取代的芴環、一經取代或未經取代的芘環、一經取代或未經取代的苯並菲、一經取代或未經取代的苯並芘、一經取代或未經取代的熒蒽環和一經取代或未經取代的苯並熒蒽環,但不限於此。前述多芳香環至少具有一取代基,該取代基可以是但不限於:氘原子、碳數為1至12的烷基、碳數為2至12的烯基、碳數為2至12的炔基或碳數為6至12的芳香基。例如,該經取代的芴環可以是經一甲基、二甲基或二甲苯基取代的芴環,即該經取代的芴環可以是9-甲基芴環(9-methylfluorene ring)、9,9-二甲基芴環(9,9-dimethylfluorene ring)或9,9-二甲苯基芴環(9,9-diphenylfluorene ring)。
舉例來說,該化合物可以下列式(I-I)至(I-XII)表示:
在上式(I-I)至(I-XII)中,n1是0至4的正整數,T可以是但不限於:氫原子、氘原子、甲基、乙基、丙基、丁基、戊基、己基或苯基。
較佳的,式(I)中Z1至Z8中至少一者是選自於由下列所構成的群組:具有至少一官能基且碳數為1至40的烷基、具有至少一官能基且碳數為2至40的烯基、具有至少一官能基且碳數為2至40的炔基、具有至少一官能基且環上碳數為3至60的環烷基、具有至少一官能基且環上碳數為3至60的雜環烷基、具有至少一官能基且環上碳數為6至60的芳香基、具有至少一官能基且環上碳數為3至60的雜芳基、具有至少一官能基且碳數為1至40的烷氧基、具有至少一官能基且環上碳數為6至60的芳氧基、具有至少一官能基且碳數為1至40的矽烷基、具有至少一官能基且環上碳數為6至60的芳矽基、具有至少一官能基且碳數為1至40的硼烷基、具有至少一官能基且環上 碳數為6至60的芳硼基、具有至少一官能基且碳數為1至40的膦基和具有至少一官能基且碳數為1至40的氧膦基。該至少一官能基是選自於由下列所構成的群組:一氰基、一硝基、一三氟甲基、一氟基和一氯基。而式(I)中Z1至Z8中的其他者可以是氫原子、氘原子或其他前述的取代基,該官能基係選自於由氰基、硝基、三氟甲基、氟基和氯基所構成的群組。
更佳的,式(I)中Z1至Z8中至少一者是一特定芳香取代基,該特定芳香取代基是選自於由下列所構成的群組:
其中,R1至R7係各自獨立選自於由下列所構成的群組:氫原子、氘原子、三氟甲基、鹵基、氰基、硝基、碳數為1至12的烷基、碳數為2至12的烯基、碳數為2至12的炔基、環上碳數為3至30的環烷基、環上碳數為3至30的雜環烷基、環上碳數為6至30的芳香基、環上碳數為3至20的雜芳基、碳數為1至40的烷氧基、環上碳數為6至30的芳氧基、碳數為1至40的矽烷基、環上碳數為6至30的芳矽基、碳數為1至40的硼烷基、環上碳數為6至30的芳硼基、碳數為1至30的膦基和碳數為1至30的氧膦基;其中n為0至4的正整數;m為0至3的正整數;o是0至3的正整數;m和o的總和小於或等於5。
較佳的,R1至R3各自獨立為苯基、吡啶基、嘧啶基、吡嗪基、健嗪基、苯並吡啶基、苯並嘧啶基、苯並吡嗪基或苯並噠嗪基,但不限於此。
較佳的,式(I)中Z1、Z2、Z3、Z6、Z7和Z8中至少一者是前述特定芳香取代基;Z4和Z5各自獨立選自於由下列構成的群組:氫原子、氘原子、碳數為1至12的烷基、碳數為2至12的烯基和碳數為2至12的炔基。或者,式(I)中Z2、Z3、Z6和Z7中至少一者是前述特定芳香取代基,且Z1、Z4、Z5、Z8各自獨立選自於由下列構成的群組:氫原子、氘原子、碳數為1至12的烷基、碳數為2至12的烯基和碳數為2至12的炔基。
更佳的,式(I)中Z2、Z3、Z6和Z7中至少一者是選自於由下列構成的群組:
更佳的,式(I)中Z1、Z2、Z3、Z6、Z7和Z8中至少一者是一經二苯基、二吡啶基、二嘧啶基、二吡嗪基、二噠嗪基、二苯並吡啶基、二苯並嘧啶基、二苯並吡嗪基或二苯並噠嗪基取代的三嗪基(triazine group)。
根據本發明,式(I)中的Z1和Z8可以是相同或是不同,Z2和Z7可以是相同或是不同,Z3和Z6可以是相同或是不同;於其中一實施例,Z1、Z2、Z3、Z6、Z7和Z8中的任其中二者可以是上述相同的取代基,而Z1、Z2、Z3、Z6、Z7和Z8中其他者可以選自於由下列所構成的群組:氫原子、氘原子、鹵基、氰基、硝基、三氟甲基、碳數為1至12的烷基、碳數為2至12的烯基和碳數為2至12的炔基。
例如,Z1、Z4至Z8各自獨立為氫原子或氘原子,Z2和/或Z3是前述特定芳香取代基;或者,Z1、Z2、Z4、Z5、Z7和Z8各自獨立為氫原子或氘原子,Z3和Z6皆為前述特定芳香取代基。
於式(I)中,Z9和Z10可以是相同或是不同的取代基,較佳的,Z9和Z10各自獨立選自於由下列所構成的群組:氫原子、氘原子、三氟甲基、鹵基、氰基、硝基、碳數為1至40的烷基、碳數為2至40的烯基、碳數為2至40的炔基、環上碳數為3至60的環烷基、環上碳數為3至60的雜環烷基、環上碳數為6至60的芳香基和環上碳數為3至60的雜芳基。更佳的,Z9和Z10各自獨立選自於由下列所構成的群組:氫原子、氘原子、三氟甲基、氟基、溴基、氰基、硝基、碳數為1至40的烷基、碳數為2至40的烯基、碳數為2至40的炔基、環上碳數為6至60的芳香基和環上碳數為3至60的雜芳基。
具體而言,該化合物可以選自於由下列所構成的群組:
本發明提供了一種有機電子裝置,該有機電子裝置包括一第一電極、一第二電極和設置於該第一電極和該第二電極間的一有機層,該有機層具有前述化合物。
較佳的,該有機電子裝置為一有機發光二極體。更佳的,本發明的新穎化合物可被用於形成電子傳輸層或電洞阻擋層的材料。
具體而言,該有機發光二極體包括:一電洞注入層、一電洞傳輸層、一發光層、一電子傳輸層和一電子注入層;該電洞注入層形成於該第一電極上;該電洞傳輸層形成於該電洞注入層上;該發光層形成於該電洞傳輸層上;該電子傳輸層形成於該發光層上;該電子注入層形成於該電子傳輸層和該第二電極之間。
於其中一實施例,該有機層可以為電子傳輸層,即該電子傳輸層包含前述的新穎化合物。
較佳的,該電洞注入層可以為一雙層結構,即該OLED於第一電極和電洞傳輸層之間具有一第一電洞注入層和一第二電洞注入層。
較佳的,該電洞傳輸層亦可以為一雙層結構,即該OLED於電洞注入層的雙層結構與發光層之間具有一第一電洞注入層和一第二電洞注入層。
較佳的,該電子傳輸層可以由新穎化合物(如所述化合物I至CLXXXVI)所製成,本發明的OLED相較於商業上的OLED具有較佳的電流效率。其中,商業上OLED中使用的已知傳輸層材料如2-{4-[9,10-二(2-萘基)-2-蒽基]苯基}-1-苯基-1H-苯並[d]咪唑(2-[4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl]-1-phenyl-1H-benzo[d]imidazole)、聯(2-甲基-8-羥基喹啉)(p-苯基苯酚)鋁(bis(2-methyl-8-quinolinolato)(p-phenylphenolato)aluminum)或2-(4-聯苯 基)-5-(4-叔丁基苯基)-1,3,4-惡二唑(2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole),PBD)。
較佳的,該OLED包括一電洞阻擋層,該電洞阻擋層形成於電子傳輸層和發光層之間,可防止電洞由發光層移動至電子傳輸層,所述電洞阻擋層可由上述新穎化合物、2,9-二甲基-4,7-聯苯基-1,10-鄰二氮雜菲(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline,BCP)或2,3,5,6-四甲基-1-苯基-1,4-鄰苯二甲醯亞胺(2,3,5,6-tetramethyl-phenyl-1,4-(bis-phthalimide),TMPP)所形成,但並不僅限於此。
較佳的,該OLED包括一電子阻擋層,該電子阻擋層形成於電洞傳輸層和發光層之間,可防止電子由發光層移動至電洞傳輸層,所述電子阻擋層可由9,9’-(1,1’-聯苯基)-4,4’-二基二-9H-咔唑(9,9'-(1,1'-biphenyl)-4,4'-diylbis-9H-carbazole,CBP)或4,4',4"-三(N-咔唑基)三苯胺(4,4',4"-tri(N-carbazolyl)-triphenylamine,TCTA)所形成,但並不僅限於此。
當OLED設置有電洞阻擋層和/或電子阻擋層時,本發明的OLED相較於傳統的OLED具有較高的發光效率。
所述第一和第二電洞傳輸層可以由N 1 ,N 1’ -(聯苯-4,4’-二基)二(N 1 -(1-萘基))-N 4 ,N 4' -二苯基苯-1,4-二胺(N 1 ,N 1’ -(biphenyl-4,4'-diyl)bis(N 1 -(naphthalen-1-yl)-N 4 ,N 4’ -diphenylbenzene-1,4-diamine))或N 4 ,N 4' -二(萘-1-基)-N 4 ,N 4’ -二苯聯苯基-4,4'-二胺(N 4 ,N 4' -di(naphthalen-1-yl)-N 4 ,N 4’ -diphenylbiphenyl-4,4'-diamine,NPB)所製成。
所述電洞注入層可由聚苯胺或聚乙烯基二氧噻吩(polvethylenedioxythiophene)所製成,但並不僅限於此。
所述發光層可由一發光材料製成,該發光材料包括一主發光體(host)和一摻雜物(dopant),其中發光材料中的主發光體可以是但不限於9-[4-(1-萘基)苯基]-10-(2-萘基)蒽(9-(4-(naphthalen-1-yl)phenyl)-10-(naphthalen-2-yl)anthracene)。
針對紅光OLED,發光層中的摻雜物(dopant)可以為具有苝配位基(perylene ligands)、熒蒽配位基(fluoranthene ligands)或二茚並配位基(periflanthene ligands)的二價銥有機金屬化合物,但不限於此。針對綠光OLED,發光層中的摻雜物可以為二氨基芴(diaminofluorenes)、蒽二胺(diaminoanthracenes)或具有苯基吡啶配位基(phenylpyridine ligands)的二價銥有機金屬化合物,但不限於此。針對藍光OLED,發光層中的摻雜物可以為二氨基芴、蒽二胺、芘二胺(diaminopyrenes)或具有苯基吡啶配位基的二價銥有機金屬化合物,但不限於此。藉由不同的主發光體材料,OLED可發出紅光、綠光或藍光。
所述電子注入層可以一電子注入材料製成,例如8-氧代萘-1-基鋰[(8-oxidonaphthalen-1-yl)lithium(II)],但不限於此。
所述第一電極可以為氧化銦錫電極(indium-doped tin oxide electrode),但並不僅限於此。
所述第二電極的功函數(work function)低於第一電極的功函數。因此,第二電極可以是但不侷限於鋁電極、銦電極或鎂電極。
本發明的其他目的、功效和技術特徵,會以圖式、實施例和比較例進行更詳細的說明。
11‧‧‧基板
12‧‧‧陽極
13‧‧‧電洞注入層
14‧‧‧電洞傳輸層
15‧‧‧發光層
16‧‧‧電子傳輸層
17‧‧‧電子注入層
18‧‧‧陰極
圖1為OLED的側視剖面圖。
圖2至圖19分別為化合物1至18的氫核磁共振光譜圖。
以下列舉數種實施例作為例示說明本發明的化合物及其有機電子裝置的實施方式,以突顯本發明相較於現有技術的差異;熟習此技藝者可經由本說明書的內容輕易了解本發明所能達成的優點與功效,並且於不悖離本發明之精神下進行各種修飾與變更,以施行或應用本發明的內容。
中間物A1的合成
中間物A1(Intermediate A1)係用於製備一種新穎化合物,中間物A1可藉由下述合成機制A1中的步驟進行合成。
步驟1:合成中間物A1-1
混合86克(1.0當量)的3-溴二苯並[a,d]環庚烯-5-酮(3-bromodibenzo[a,d]cyclohepten-5-one)、106克(2.0當量)的N-溴代丁二醯亞胺(N-bromosuccinimide,NBS)和0.7克(0.01當量)的過氧化苯甲醯(benzyl peroxide)於430毫升的四氯化碳(carbon tetrachloride,CCl4)中,並加熱至85℃進行反應,在反應的過程中以高效液相層析儀(high performance liquid chromatography,HPLC)進行監測;當反應完成後,過濾分離反應所產生的沉澱物,使沉澱物以甲醇沖洗並再結晶純化,再經濃縮和乾燥後可獲得123 克的白色固體產物,產率為92.3%。經場脫附質譜(field desorption mass spectroscopy,FD-MS)分析確定,白色固體產物即為中間物A1-1。FD-MS分析結果:C15H9Br3O,理論值444.94,檢測值444.94。
步驟2:合成中間物A1
使中間物A1-1(1.0當量)溶於二甲基亞碸(dimethyl sulfoxide,DMSO)(相對於反應物w/v=1/3)中並加熱至70℃,反應過程中以HPLC監測,在反應完成後,以冰水急速冷卻並將沉澱物過濾再以矽膠管柱層析純化,可獲得淡黃色固體產物中間物A1,產率為93%。經FD-MS分析確定,。FD-MS分析的結果:C15H9BrO,理論值285.14,檢測值為285.14。
中間物A2的合成
中間物A2係用於製備一種新穎化合物,中間物A2是以類似於合成中間物A1的步驟1和步驟2,其差異在於:起始物3-溴二苯並[a,d]環庚烯-5-酮以2-溴二苯並[a,d]環庚烯-5-酮(CAS No.198707-82-3)代替,中間物A2的合成路徑統整於合成機制A2中,在合成機制A2中所有中間物的分析方法皆同前述,分析結果列於下表1。
中間物A3的合成
中間物A3係用於製備一種新穎化合物,中間物A3是以類似於合成中間物A1的步驟1和步驟2所合成,其差異在於起始物3-溴二苯並[a,d]環庚烯-5-酮以3,7-二溴二苯並[a,d]環庚烯-5-酮 (3,7-dibromodibenzo[a,d]cyclohepten-5-one)(CAS No.226946-20-9)代替,中間物A3的合成路徑統整於合成機制A3中,在合成機制A3中所有中間物的分析方法皆同前述,分析結果列於下表1。
中間物A1至A3的修飾
除了中間物A1至A3之外,所屬技術領域具有通常知識者可更替合成機制A1至A3中的起始物,並以類似於合成機制A1至A3的合成路徑合成出其他中間物,例如以下列出的中間物A4至A15:
中間物B1和B3至B6的合成
中間物B1和B3至B6是將1-溴-2-碘苯(1-bromo-2-iodobenzene)與芳基硼酸反應而得,以下將芳基硼酸稱為「反應物An(Reactant An)」,中間物Bn的合成路徑係如合成機制B-1所示。在合成機制B-1中,「反應物An」係選自下表2中的反應物A1至A5;「中間物Bn(Intermediate Bn)」係選自下表2中的中間物B1和B3至B6。
根據合成機制B1,中間物B1和B3至B6係根據以下步驟進行合成。
1當量的1-溴-2碘苯、1.2當量的反應物An、3.0當量的碳酸鉀、200毫升的甲苯、0.06當量的三苯基膦(Triphenylphosphine,PPh3)和0.015當量的乙酸鈀於70℃下混合,當反應完成後,使混合液冷卻至室溫後,藉由飽和食鹽水和EA萃取獲得有機層並以硫酸鎂除水,接著以矽膠過濾,再將濾物以己烷洗滌並過濾獲得中間物Bn。在合成機制B中所有中間物Bn的分析方法皆同前述,分析結果列於下表2。
中間物B2的合成
除了合成機制B-1之外,中間物B2可另以合成機制B-2合成。
步驟1:中間物B2-1的合成
混合0.05當量的雙三苯基磷二氯化鈀[dichlorobis-(triphenylphosphine)palladium),Pd(PPh3)2Cl2]、1當量的2-溴苯甲醛、四氫呋喃(tetrahydrofuran,THF)(0.13至0.15M)和3當量的三乙基甲胺,在室溫攪拌10分鐘後將1.5當量的苯乙炔和0.05當量的碘化銅加入混合溶液中,並使之在室溫下攪拌24小時,接著以飽和氯化銨水溶液急速冷卻反應溶液,並以醋酸乙酯萃取有機相、以硫酸鎂乾燥、過濾再於低壓環境下濃縮產物,將濃縮後的粗產物以矽膠管柱層析純化獲得中間物B2-1,產率為92.4%,產物經FD-MS分析結果為:C15H10O,理論分子量為206.64,測量分子量為206.64。
步驟2:中間物B2的合成
將1.0當量的中間物B2-1、0.05當量的三氟甲烷磺酸铜(Copper(II)trifluoromethanesulfonate,Cu(OTf)2)、反應物的五倍體積的1,2-二氯乙烷在室溫、氬氣的環境中依序加入1.2當量的1-(2-溴乙炔基)苯和1.0當量的三氟乙酸中,接著加熱至100℃攪拌15分鐘再靜置冷卻至室溫,加入飽和的碳酸氫鈉水溶液並以乙醚萃取三次,合併萃取而得的有機相後以鹽水洗滌、以硫酸鎂乾燥再使溶劑揮發獲得粗產物,將粗產物以己烷作為洗 提液並以矽膠管柱層析純化獲得中間物B2,產率為80%,產物經FD-MS分析結果為:C16H11Br,理論分子量為283.16,測量分子量為283.16。
中間物B1至B6的修飾
除了前述中間物B1至B6,所屬技術領域具有通常知識者可藉由採用有別於反應物A1至A5的芳基硼酸與1-溴-2碘苯反應,以類似於合成機制B-1的合成步驟成功合成其他中間物Bn;同樣的,所屬技術領域具有通常知識者亦可使用類似於合成機制B-2的方式合成出其他中間物Bn。例如下列中間物B7至B14:
中間物C的合成
前述中間物B1至B14(尤其指中間物B1至B6)可另用於合成中間物Cn,中間物Cn的合成路徑係如合成機制C-1所示。在合成機制C-1中,「中間物An」係選自於包括中間物A1至A15及其相似物的群組;「中間物Bn」係選自於包括中間物B1至B14及其相似物的群組;「中間物Cn」係選自於表3-1中包括中間物C1至C9的群組;中間物C1至C9分別以下述步驟所合成。
步驟1:醇中間物(中間物Cn-1)的合成
1.0當量的中間物Bn溶於120毫升、0.4M的THF中,降溫至-78℃後緩慢加入1.0當量、2.5M的正丁基鋰(n-Butyllithium,n-BuLi)並攪拌1小時,接著將0.7當量的中間物An加入反應溶液中並於室溫下再攪拌3小時,反應完成後,以飽和氯化銨水溶液冷卻反應溶液並萃取有機相,分離有機相後以石油醚再結晶產物獲得白色產物,經FD-MS分析後確定為中間物Cn-1,各中間物Cn-1的化學結構式及FD-MS的測量結果列於表3-1中。
步驟2:中間物Cn的合成
將1.0當量的中間物Cn-1、醋酸(相較於反應物w/v=1/3)和五滴硫酸混合並於110℃下攪拌6小時,再以旋轉蒸發器去除溶劑,並藉由管柱層析純化,再以甲苯使殘餘物在結晶獲得中間物Cn,中間物Cn以FD-MS分析確定,並將分析結果列於表3-1中。
中間物C1至C9的修飾
除了前述中間物C1至C9,所屬領域具有通常知識者可藉由置換除了中間物A1至A3外的其他中間物An,或是置換除了中間物B1至B6的其他中間物Bn,使用類似於反應機制C-1的合成路徑合成出其他中間物Cn,例如下列的中間物C10至C21:
中間物C18; 中間物C19; 中間物C20;和 中間物C21。
中間物Cn-B的合成
前述中間物Cn可再藉由Miyaura硼基化反應(Miyaura borylation reaction)進一步修飾為中間物Cn-B,「中間物Cn-B」是將中間物Cn的溴基取代為頻那醇硼基[(pinacolato)boron group],中間物Cn-B可藉由下述合成機制C1-B中的合成路徑合成。
1.2當量的聯硼酸頻那醇酯[bis(pinacolato)diboron]、1.0當量的中間物Cn、0.015當量的[1,1-雙(二苯基膦基)二茂鐵]二氯化鈀[1,1-bis(diphenylphosphino)-ferrocene dichloropalladium(II),PdCl2(dppf)]和3.0當量的醋酸鉀於在0.3M的無水1,4-二噁烷(1,4-dioxane)中形成的混合溶液,並在110℃的氮氣環境下攪拌8小時,待冷卻至室溫後,於低壓環境下去除溶劑,並將殘餘物以管柱層析純化獲得白黃色產物。該白黃色產物的化學結構式和產率以及FD-MS分析的分子式和質量結果列於表3-2中。
中間物Cn-B的修飾
除了上述中間物Cn和Cn-B之外,所屬領域具有通常知識者可任選自前述中間物Cn所構成的群組,並以類似於合成機制C1-B的方式對任一中間物Cn進行Miyaura硼基化反應以合成中間物Cn-B。
新穎化合物的合成
前述中間物Cn和Cn-B可藉由合成機制I來合成新穎化合物,於合成機制I中,「反應物Bn」係選自於表4中包括反應物B1至B25的群組;「中間物C」係包含前述中間物Cn、Cn-B及其相似物。
1.0當量的中間物Cn、2.1當量的反應物Bn、0.01當量的醋酸鈀、0.04當量的2-(二環己基磷基)聯苯[dicyclohexylphosphine(2-biphenyl),P(Cy)2(2-biPh)]、甲苯/乙醇(0.5M、v/v=10/1)和3.0M的碳酸鉀水溶液混合,於氮氣環境下以100℃的溫度下回流12小時,反應完全後,將水和甲苯加入反應物溶液中,接著,使用溶劑將有機相萃取出來並以硫酸鈉乾燥,於低壓環境下使溶劑揮發後利用矽膠管柱層析純化剩餘物,並以甲苯再結晶獲得新穎化合物
用以合成化合物I至XVIII的反應物Bn和中間物Cn列於表5中,各化合物I至XVIII分別以氫核磁共振光譜儀(H1-NMR)和FD-MS分析確定,化合物I至XVIII的氫核磁共振光譜圖如依序為圖2至圖19,且化合物I 至XVIII的化學結構式、產率、分子式和質量列於表5中。
化合物I至XVIII的修飾
除了前述化合物I至XVIII之外,所屬技術領域具有通常知識者可更替不同的中間物C(即中間物Cn或Cn-B)和反應物Bn,並以類似於合成機制I的合成路徑合成出其他新穎化合物。
OLED裝置的製備
將塗佈有1500Å厚ITO層的玻璃基板(以下簡稱為ITO基板)置於含有洗潔劑(廠牌:Fischer Co.)的蒸餾水(以Millipore Co.公司的濾器過濾二次而得的蒸餾水)中,並以超音波震盪30分鐘;更換蒸餾水後再以超音波震盪10分鐘以洗淨ITO基板,並重複上述洗淨步驟一次;洗淨後,將前述玻璃基板以異丙醇、丙酮和甲醇以超音波震盪洗淨,並使之乾燥;接著,將玻璃基板置於電漿表面清潔機內,並以氧電漿清潔玻璃基板5分鐘,再將清潔後的玻璃基板置於真空蒸鍍機內。
之後,將真空蒸鍍機的真空度維持在1x10-6 torr至3x10-7 torr,並於ITO基板上依序沉積各種有機材料和金屬材料,並獲得實施例1至40的OLED裝置。於此,該ITO基板上係依序沉積有第一電洞注入層(HIL-1)、第二電洞注入層(HIL-2)、第一電洞傳輸層(HTL-1)、第二電洞傳 輸層(HTL-2)、藍/綠/紅發光層(BEL/GEL/REL)、電子傳輸層(ETL)、電子注入層(EIL)和陰極(Cthd)。
在上述OLED裝置的各層中,HAT是用於形成HIL-1和HIL-2;HI-2是用於形成HIL-1、HIL-2和HTL-1;HI-D是用於形成HIL-1、HT-1和HT-2;HT-1和HT-2分別是用於形成HTL-1和HTL-2;本發明的新穎化合物和傳統ET材料(BCP和TAZ)是用於形成ETL;Liq是用於形成ETD和EIL;RH-1或RH-2/GH-1或GH-2/BH分別為形成REL/GEL/BEL的主要材料;RD/GD/BD-1或BD-2可作為REL/GEL/BEL的摻雜物。實施例的OLED裝置和比較例的OLED裝置的主要差異為:比較例的OLED裝置中ETL是以BCP或TAZ製成,實施例的OELD裝置中ETL是以列於表5的新穎化合物所製成。上述各傳統材料的詳細化學結構式列於表6。
紅光OLED裝置的製備
紅光OLED裝置包括複數有機層,各有機層依序沉積於ITO基板上,用以製備第一紅光OLED和第二紅光OLED的各有機層的材料和厚度分別列於表7中,第一紅光OLED和第二紅光OLED的差異在於HIL-1、HIL-2、HTL-1和REL使用的材料。
綠光OLED裝置的製備
綠光OLED裝置包括複數有機層,各有機層依序沉積於ITO基板上,用以製備第一綠光OLED和第二綠光OLED的各有機層的材料和厚度分別列於表8中,第一綠光OLED和第二綠光OLED的差異在於HIL-1、 HIL-2、HTL-1和GEL使用的材料。
藍光OLED裝置的製備
藍光OLED裝置包括複數有機層,各有機層依序沉積於ITO基板上,用以製備第一藍光OLED和第二藍光OLED的各有機層的材料和厚度分別列於表9中,第一藍光OLED和第二藍光OLED的差異在於HIL-1、HIL-2、HTL-1和BEL使用的材料。
OLED裝置的效能
為了評估OLED裝置的效能,分別將紅光、綠光和藍光OLED裝置連接於電源供應器(廠牌:Keithley;型號:2400),並以PR650的光度計檢測,所測得之色度以為國際照明委員會(Commission Internationale de L’Eclairage 1931,CIE)制定的色度座標[color coordinate(x,y)]示之,檢測結果列於下表10中。其中,藍光和紅光的OLED裝置是在1000尼特(1 nit=1cd/m2)的亮度下檢測;綠光的OLED裝置是在3000尼特的亮度下檢測。
實施例1至40和比較例1至6中OLED裝置的ETL材料、CIE顏色、驅動電壓和電流效率列於表10中;於表10中,第一藍光OLED命名為B1,第二藍光OLED命名為B2,同樣的,第一和第二紅光OLED以及第一和第二綠光OLED依序命名為R1、R2、G1和G2。
表10:實施例1至40和比較例1至6中OLED裝置的ETL材料、顏色、CIE、驅動電壓和電流效率。
根據表10的結果,相較於用於商業上電子傳輸材料(BCP或TAZ),本發明藉由添加化合物I至XVIII於電子傳輸層中,可降低紅光、綠光或藍光OLED裝置的驅動電壓並改善電流效率,證實本發明的新穎化合物適用添加於各色OLED裝置中,並可達到降低驅動電壓和改善電流效率的功效。
上述實施例僅係為說明本創作之例示,並非於任何方面限制本創作所主張之權利範圍,所屬技術領域中具有通常知識者能根據本創作之精神針對例如取代基的數量、位置或排列加以調整。本創作所主張之權利範圍自應以申請專利範圍所述為準,而非僅限於上述具體實施例。
Claims (20)
- 一種化合物,其係如下式(I)所示:
- 如請求項1所述的化合物,其中自X 3和X 4延伸形成的該多芳香環是選自於下列所構成的群組:一經取代或未經取代的萘環、一經取代或未經取代的蒽環、一經取代或未經取代的菲環、一經取代或未經取代的芴環、一經取代或未經取代的芘環、一經取代或未經取代的苯並菲、一經取代或未經取代的苯並芘、一經取代或未經取代的熒蒽環和一經取代或未經取代的苯並熒蒽環。
- 如請求項1所述的化合物,其中該化合物係以下述式(I-I)至(I-XII)表示:
- 如請求項1所述的化合物,其中自X 1和X 2延伸形成的該芳香環是一經取代或未經取代且環上碳數為6至60的碳環。
- 如請求項4所述的化合物,其中該經取代或未經取代且環上碳數為6至60的碳環是選自於由下列所構成的群組:一經取代或未經取代的苯環、一經取代或未經取代的萘環、一經取代或未經取代的蒽環、一經取代或未經取代的菲環、一經取代或未經取代的芴環、一經取代或未經取代的芘環、一經取代或未經取代的苯並菲、一經取代或未經取代的苯并芘、一經取代或未經取代的熒蒽環和一經取代或未經取代的苯並熒蒽環。
- 如請求項5所述的化合物,其中該經取代或未經取代且環上碳數為6至60的碳環是一經取代或未經取代的苯環。
- 如請求項1所述的化合物,其中該式(I)中Z 1至Z 8中至少一者是選自於由下列所構成的群組:具有至少一官能基且碳數為1至40的烷基、具有至少一官能基且碳數為2至40的烯基、具有至少一官能基且碳數為2至40的炔基、具有至少一官能基且環上碳數為3至60的環烷基、具有至少一官能基且環上碳數為3至60的雜環烷基、具有至少一官能基且 環上碳數為6至60的芳香基、具有至少一官能基且環上碳數為3至60的雜芳基、具有至少一官能基且碳數為1至40的烷氧基、具有至少一官能基且環上碳數為6至60的芳氧基、具有至少一官能基且碳數為1至40的矽烷基、具有至少一官能基且環上碳數為6至60的芳矽基、具有至少一官能基且碳數為1至40的硼烷基、具有至少一官能基且環上碳數為6至60的芳硼基、具有至少一官能基且碳數為1至40的膦基和具有至少一官能基且碳數為1至40的氧膦基;其中,該至少一官能基是選自於由下列所構成的群組:一氰基、一硝基、一三氟甲基、一氟基和一氯基。
- 如請求項1所述的化合物,其中該式(I)中Z 1至Z 8中至少一者是選自於由下列所構成的群組:
- 如請求項1所述的化合物,其中該式(I)中Z 2、Z 3、Z 6和Z 7中至少一者是選自於由下列所構成的群組:
- 如請求項1所述的化合物,其中該式(I)中Z 2、Z 3、Z 6和Z 7中至少一者是選自於由下列所構成的群組:
- 如請求項1所述的化合物,其中該式(I)中Z 1、Z 2、Z 3、Z 6、Z 7和Z 8中至少一者是一經二苯基、二吡啶基、二嘧啶基、二吡嗪基、二健嗪基、二苯並吡啶基、二苯並嘧啶基、二苯並吡嗪基或二苯並噠嗪基取代的三嗪基。
- 如請求項1所述的化合物,其中該Z 9和Z 10各自獨立選自於由下列所構成的群組:氫原子、氘原子、三氟甲基、鹵基、氰基、硝基、 碳數為1至40的烷基、碳數為2至40的烯基、碳數為2至40的炔基、環上碳數為6至60的芳香基和環上碳數為3至60的雜芳基。
- 如請求項1所述的化合物,其中該Z 1、Z 4至Z 8各自獨立為氫原子或氘原子。
- 如請求項1所述的化合物,其中該Z 1、Z 2、Z 4、Z 5、Z 7和Z 8各自獨立為氫原子或氘原子。
- 如請求項1所述的化合物,其中該化合物是選自於由下列所構成的群組:
- 一種有機電子裝置,其包括一第一電極、一第二電極和設置於該第一電極和該第二電極間的一有機層,其中該有機層包括如請求項1至15中任一項所述的化合物。
- 如請求項16所述的有機電子裝置,其中該有機電子裝置為一有機發光二極體。
- 如請求項17所述的有機電子裝置,其中該有機發光二極體包括:一電洞注入層,其形成於該第一電極上;一電洞傳輸層,其形成於該電洞注入層上: 一發光層,其形成於該電洞傳輸層上;一電子傳輸層,其形成於該發光層上,該有機層為該電子傳輸層;和一電子注入層,其形成於該電子傳輸層和該第二電極之間。
- 如請求項17所述的有機電子裝置,其中該有機發光二極體包括:一電洞注入層,其形成於該第一電極上;一電洞傳輸層,其形成於該電洞注入層上;一發光層,其形成於該電洞傳輸層上;一電洞阻擋層,其形成於該發光層上,該有機層為該電洞阻擋層;一電子傳輸層,其形成於該電洞阻擋層上;和一電子注入層,其形成於該電子傳輸層和該第二電極之間。
- 如請求項16所述的有機電子裝置,其中該化合物係選自於由下列所構成的群組:
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TWI699357B (zh) * | 2018-06-05 | 2020-07-21 | 大陸商上海嶸彩光電材料有限公司 | 用於有機電子裝置的組合物及使用其的有機電子裝置 |
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US10693075B2 (en) | 2020-06-23 |
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CN107698570A (zh) | 2018-02-16 |
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JP2018052919A (ja) | 2018-04-05 |
JP6475795B2 (ja) | 2019-02-27 |
KR101963675B1 (ko) | 2019-03-29 |
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