CN114080387A - 化合物以及包括其的有机发光装置 - Google Patents
化合物以及包括其的有机发光装置 Download PDFInfo
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- CN114080387A CN114080387A CN202080048803.8A CN202080048803A CN114080387A CN 114080387 A CN114080387 A CN 114080387A CN 202080048803 A CN202080048803 A CN 202080048803A CN 114080387 A CN114080387 A CN 114080387A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 139
- 239000000126 substance Substances 0.000 claims abstract description 114
- 239000000463 material Substances 0.000 claims description 77
- 125000003118 aryl group Chemical group 0.000 claims description 59
- 125000001424 substituent group Chemical group 0.000 claims description 54
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 239000001257 hydrogen Substances 0.000 claims description 40
- 239000011368 organic material Substances 0.000 claims description 39
- 125000001072 heteroaryl group Chemical group 0.000 claims description 38
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 28
- 229910052805 deuterium Inorganic materials 0.000 claims description 27
- 238000002347 injection Methods 0.000 claims description 21
- 239000007924 injection Substances 0.000 claims description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 19
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical group [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 14
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 13
- 125000003277 amino group Chemical group 0.000 claims description 13
- 125000004306 triazinyl group Chemical group 0.000 claims description 13
- 125000002619 bicyclic group Chemical group 0.000 claims description 12
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000000732 arylene group Chemical group 0.000 claims description 10
- 150000001616 biphenylenes Chemical group 0.000 claims description 10
- 230000000903 blocking effect Effects 0.000 claims description 10
- 230000005525 hole transport Effects 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- VAVIOKVTPDHSOL-UHFFFAOYSA-N biphenylene triphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1.C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 VAVIOKVTPDHSOL-UHFFFAOYSA-N 0.000 claims description 9
- 125000002883 imidazolyl group Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- 125000001181 organosilyl group Chemical class [SiH3]* 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 3
- 239000010410 layer Substances 0.000 description 109
- -1 1-methylpentyl Chemical group 0.000 description 75
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 21
- 125000001624 naphthyl group Chemical group 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 235000010290 biphenyl Nutrition 0.000 description 13
- 239000012153 distilled water Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000004305 biphenyl Substances 0.000 description 12
- 125000004122 cyclic group Chemical group 0.000 description 12
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 12
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 11
- 125000000753 cycloalkyl group Chemical group 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 239000000758 substrate Substances 0.000 description 11
- 238000001035 drying Methods 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 9
- 238000004770 highest occupied molecular orbital Methods 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 9
- 239000010409 thin film Substances 0.000 description 9
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 8
- 238000000151 deposition Methods 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 125000003367 polycyclic group Chemical group 0.000 description 8
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 8
- 125000005580 triphenylene group Chemical group 0.000 description 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 6
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 6
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 125000005561 phenanthryl group Chemical group 0.000 description 6
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 6
- 125000001725 pyrenyl group Chemical group 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- 125000005549 heteroarylene group Chemical group 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 229910052710 silicon Inorganic materials 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 125000006836 terphenylene group Chemical group 0.000 description 5
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 4
- 125000006267 biphenyl group Chemical group 0.000 description 4
- 229920001940 conductive polymer Polymers 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 229920000767 polyaniline Polymers 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- DDGPPAMADXTGTN-UHFFFAOYSA-N 2-chloro-4,6-diphenyl-1,3,5-triazine Chemical compound N=1C(Cl)=NC(C=2C=CC=CC=2)=NC=1C1=CC=CC=C1 DDGPPAMADXTGTN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000010405 anode material Substances 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000010406 cathode material Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 description 3
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 3
- 125000005493 quinolyl group Chemical group 0.000 description 3
- 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 2
- SSJXIUAHEKJCMH-PHDIDXHHSA-N (1r,2r)-cyclohexane-1,2-diamine Chemical compound N[C@@H]1CCCC[C@H]1N SSJXIUAHEKJCMH-PHDIDXHHSA-N 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 2
- 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
- GAQKEAQMVDKCAF-UHFFFAOYSA-N 1-bromo-2-chloro-4-iodobenzene Chemical compound ClC1=CC(I)=CC=C1Br GAQKEAQMVDKCAF-UHFFFAOYSA-N 0.000 description 2
- USYQKCQEVBFJRP-UHFFFAOYSA-N 1-bromo-3-phenylbenzene Chemical group BrC1=CC=CC(C=2C=CC=CC=2)=C1 USYQKCQEVBFJRP-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- MAGFQRLKWCCTQJ-UHFFFAOYSA-M 4-ethenylbenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(C=C)C=C1 MAGFQRLKWCCTQJ-UHFFFAOYSA-M 0.000 description 2
- KDOQMLIRFUVJNT-UHFFFAOYSA-N 4-n-naphthalen-2-yl-1-n,1-n-bis[4-(n-naphthalen-2-ylanilino)phenyl]-4-n-phenylbenzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=C(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=C1 KDOQMLIRFUVJNT-UHFFFAOYSA-N 0.000 description 2
- SNFCXVRWFNAHQX-UHFFFAOYSA-N 9,9'-spirobi[fluorene] Chemical compound C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=CC=C21 SNFCXVRWFNAHQX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 125000005577 anthracene group Chemical group 0.000 description 2
- 125000005264 aryl amine group Chemical group 0.000 description 2
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 description 2
- 125000000532 dioxanyl group Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000434 field desorption mass spectrometry Methods 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 description 2
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 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 2
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 2
- 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 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 2
- 238000009832 plasma treatment Methods 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000002207 thermal evaporation Methods 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 238000002061 vacuum sublimation Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- CRXBTDWNHVBEIC-UHFFFAOYSA-N 1,2-dimethyl-9h-fluorene Chemical compound C1=CC=C2CC3=C(C)C(C)=CC=C3C2=C1 CRXBTDWNHVBEIC-UHFFFAOYSA-N 0.000 description 1
- QTPLEVOKSWEYAC-UHFFFAOYSA-N 1,2-diphenyl-9h-fluorene Chemical compound C=1C=CC=CC=1C1=C2CC3=CC=CC=C3C2=CC=C1C1=CC=CC=C1 QTPLEVOKSWEYAC-UHFFFAOYSA-N 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- VFBJMPNFKOMEEW-UHFFFAOYSA-N 2,3-diphenylbut-2-enedinitrile Chemical group C=1C=CC=CC=1C(C#N)=C(C#N)C1=CC=CC=C1 VFBJMPNFKOMEEW-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- WONYVCKUEUULQN-UHFFFAOYSA-N 2-methyl-n-(2-methylphenyl)aniline Chemical group CC1=CC=CC=C1NC1=CC=CC=C1C WONYVCKUEUULQN-UHFFFAOYSA-N 0.000 description 1
- HONWGFNQCPRRFM-UHFFFAOYSA-N 2-n-(3-methylphenyl)-1-n,1-n,2-n-triphenylbenzene-1,2-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C(=CC=CC=2)N(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 HONWGFNQCPRRFM-UHFFFAOYSA-N 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000006027 3-methyl-1-butenyl group Chemical group 0.000 description 1
- LOIBXBUXWRVJCF-UHFFFAOYSA-N 4-(4-aminophenyl)-3-phenylaniline Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1C1=CC=CC=C1 LOIBXBUXWRVJCF-UHFFFAOYSA-N 0.000 description 1
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Abstract
本说明书涉及一种由化学式1表示的化合物以及一种包含其的有机发光装置。
Description
技术领域
本说明书涉及一种化合物以及包含其的有机发光装置。
本说明书主张2019年11月25日向韩国知识产权局申请的韩国专利申请案第10-2019-0152361号的优先权及权益,其全部内容以引用的方式并入本文中。
背景技术
电致发光装置是一种类型的自动发光显示装置,且具有以下优势:具有广视角及较快回应速度以及具有极佳对比度。
有机发光装置具有在两个电极之间安置有机薄膜的结构。当将电压施加至具有此种结构的有机发光装置时,自两个电极注入的电子及空穴在有机薄膜中结合且配对,且在所述电子及空穴湮灭时发光。有机薄膜可视需要以单层或多层的形式形成。
有机薄膜的材料可视需要具有发光功能。举例而言,作为有机薄膜的材料,可单独使用能够形成发光层本身的化合物,或亦可使用能够起到主体-掺杂剂类发光层的主体或掺杂剂作用的化合物。另外,亦可使用能够起空穴注入、空穴传输、电子阻挡、空穴阻挡、电子传输、电子注入以及类似作用的化合物作为有机薄膜的材料。
有机薄膜材料的发展不断要求增强有机发光装置的效能、使用寿命或效率。
发明内容
技术问题
本说明书是关于提供一种化合物以及包含其的有机发光装置。
技术解决方案
本说明书的一个实施例提供一种由以下化学式1表示的化合物。
[化学式1]
在化学式1中,
A1及A2中的一者为(L1)a-Q1,
A1及A2中的另一者及A3以及A4各自独立地为氢;氘;或(L2)b-Q2,且其至少一者为(L2)b-Q2,
a及b各自独立地为1至5的整数,
当a及b各自为2或大于2时,括弧中的取代基彼此相同或不同,
L1及L2各自独立地为直接键;经取代或未经取代的C6至C60亚芳基;或经取代或未经取代的C2至C60亚杂芳基,
Q1为经取代或未经取代的C6至C20芳基;或包含N的经取代或未经取代的C2至C20杂芳基,
Q2为氰基;经取代或未经取代的硅基;经取代或未经取代的胺基;经取代或未经取代的C1至C20烷基;经取代或未经取代的C6至C30芳基;经取代或未经取代的C2至C30杂芳基;或经取代或未经取代的氧化膦基团,
当A2及A3为氢时,Q1为苯基且Q2包含吡啶或三嗪,L1为经取代或未经取代的C6至C60亚芳基;或经取代或未经取代的C2至C60亚杂芳基,以及
当Q1及Q2皆为芳基时,满足以下中的一者:i)Q1及Q2皆为苯基,L1及L2为直接键,且A2及A4为氢;ii)Q1及Q2皆为苯基,L1及L2中的至少一者为经取代或未经取代的双环或低碳亚芳基;或经取代或未经取代的C2至C60亚杂芳基;以及iii)Q1及Q2中的至少一者为未经取代或经烷基或芳基取代的双环或高碳芳基。
本申请案的另一实施例提供一种有机发光装置,其包含:第一电极;第二电极,设置为与第一电极相对;以及有机材料层,设置于第一电极与第二电极之间,其中有机材料层包含一或多种类型的由化学式1表示的化合物。
有利作用
本说明书中所描述的化合物可用作有机发光装置的有机材料层的材料。化合物能够在有机发光装置中起空穴注入材料、空穴传输材料、发光材料、电子传输材料、电子注入材料或类似材料的作用。特定言之,化合物可用作有机发光装置的发光层材料。
另外,当使用两种类型的化学式1的化合物或使用化学式1的化合物及化学式2的化合物两者作为有机发光装置的发光层材料时,可降低装置的驱动电压,可增强光效率,且可增强装置的使用寿命特性。
附图说明
图1至图3为各自示出根据本说明书的一个实施例的有机发光装置的层压结构的附图。
100:基板
200:阳极
300:有机材料层
301:空穴注入层
302:空穴传输层
303:发光层
304:空穴阻挡层
305:电子传输层
306:电子注入层
400:阴极
具体实施方式
在下文中,将更详细地描述本说明书。
在本说明书中,“包含”某些成分的某一部分意谓能够还包含其他成分,且除非相反地特定陈述,否则不排除其他成分。
术语“取代”意谓结合至化合物的碳原子的氢原子正变成另一取代基,且只要取代位置为氢原子经取代的位置,亦即取代基可取代的位置,则取代位置不受限制,且在两个或大于两个取代基取代时,所述两个或大于两个取代基可彼此相同或不同。
在本说明书中,“经取代或未经取代”意谓经一或多个由以下所组成的族群中选出的取代基取代:氘;卤基;氰基;C1至C60直链或分支链烷基;C2至C60直链或分支链烯基;C2至C60直链或分支链炔基;C3至C60单环或多环环烷基;C2至C60单环或多环杂环烷基;C6至C60单环或多环芳基;C2至C60单环或多环杂芳基;硅基;氧化膦基团;以及胺基,或经连接由上文示出的取代基中选出的两个或大于两个取代基的取代基取代,或未经取代。
在本说明书中,“在化学式或化合物结构中未指示取代基的情况”意谓氢原子结合至碳原子。然而,由于氘(2H)为氢的同位素,因此一些氢原子可为氘。
在本申请案的一个实施例中,“在化学式或化合物结构中未指示取代基的情况”可意谓可出现取代基的位置可全部为氢或氘。换言之,由于氘为氢的同位素,因此一些氢原子可为作为同位素的氘,且在本文中,氘的含量可为0%至100%。
在本申请案的一个实施例中,在“化学式或化合物结构中未指示取代基的情况”中,当未明确地排除氘(诸如氘含量为0%,氢含量为100%或取代基皆为氢)时,氢及氘可在化合物中混合。
在本申请案的一个实施例中,氘为氢的同位素中的一者,为具有由一个质子及一个中子形成的氘核作为原子核的元素,且可表示为氢-2,且元素符号亦可写作D或2H。
在本申请案的一个实施例中,同位素意谓具有相同原子数(Z)但具有不同质量数(A)的原子,且亦可解释为具有相同质子数但具有不同中子数的元素。
在本申请案的一个实施例中,特定取代基的含量T%的含义可定义为T2/T1×100=T%,其中基础化合物可具有的取代基的总数目定义为T1,且此等取代基中的特定取代基的数目定义为T2。
换言之,在一个实例中,在由表示的苯基中具有20%的氘含量意谓苯基可具有的取代基的总数目为5(公式中的T1),且此等取代基中的氘数目为1(公式中的T2)。换言之,在苯基中具有20%的氘含量可由以下结构式表示。
另外,在本申请案的一个实施例中,“具有0%的氘含量的苯基”可意谓不包含氘原子的苯基,亦即,具有5个氢原子的苯基。
在本说明书中,卤素可为氟、氯、溴或碘。
在本说明书中,烷基包含具有1个至60个碳原子的直链或分支链,且可进一步经其他取代基取代。烷基的碳原子数可为1至60,特定言之1至40且更特定言之1至20。其特定实例可包含甲基、乙基、丙基、正丙基、异丙基、丁基、正丁基、异丁基、第三丁基、第二丁基、1-甲基-丁基、1-乙基-丁基、戊基、正戊基、异戊基、新戊基、第三戊基、己基、正己基、1-甲基戊基、2-甲基戊基、4-甲基-2-戊基、3,3-二甲基丁基、2-乙基丁基、庚基、正庚基、1-甲基己基、环戊基甲基、环己基甲基、辛基、正辛基、第三辛基、1-甲基庚基、2-乙基己基、2-丙基戊基、正壬基、2,2-二甲基庚基、1-乙基-丙基、1,1-二甲基-丙基、异己基、2-甲基戊基、4-甲基己基、5-甲基己基以及类似基团,但不限于此。
在本说明书中,烯基包含具有2个至60个碳原子的直链或分支链,且可进一步经其他取代基取代。烯基的碳原子数可为2至60,特定言之2至40且更特定言之2至20。其特定实例可包含乙烯基、1-丙烯基、异丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-戊烯基、2-戊烯基、3-戊烯基、3-甲基-1-丁烯基、1,3-丁二烯基、烯丙基、1-苯基乙烯基-1-基、2-苯基乙烯基-1-基、2,2-二苯基乙烯基-1-基、2-苯基-2-(萘基-1-基)乙烯基-1-基、2,2-双(二苯基-1-基)乙烯基-1-基、芪基(stilbenyl group)、苯乙烯基以及类似基团,但不限于此。
在本说明书中,炔基包含具有2个至60个碳原子的直链或分支链,且可进一步经其他取代基取代。炔基的碳原子数可为2至60,特定言之2至40且更特定言之2至20。
在本说明书中,环烷基包含具有3个至60个碳原子的单环或多环,且可进一步经其他取代基取代。在本文中,多环意谓其中环烷基直接连接至其他环状基团或与其他环状基团稠合的基团。在本文中,其他环状基团可为环烷基,但亦可为不同类型的环状基团,诸如杂环烷基、芳基以及杂芳基。环烷基的碳基团数可为3至60,特定言之3至40且更特定言之5至20。其特定实例可包含环丙基、环丁基、环戊基、3-甲基环戊基、2,3-二甲基环戊基、环己基、3-甲基环己基、4-甲基环己基、2,3-二甲基环己基、3,4,5-三甲基环己基、4-第三丁基环己基、环庚基、环辛基以及类似基团,但不限于此。
在本说明书中,杂环烷基包含作为杂原子的O、S、Se、N或Si,包含具有2个至60个碳原子的单环或多环,且可进一步经其他取代基取代。在本文中,多环意谓其中杂环烷基直接连接至其他环状基团或与其他环状基团稠合的基团。在本文中,其他环状基团可为杂环烷基,但亦可为不同类型的环状基团,诸如环烷基、芳基以及杂芳基。杂环烷基的碳原子数可为2至60,特定言之2至40且更特定言之3至20。
在本说明书中,芳基包含具有6个至60个碳原子的单环或多环,且可进一步经其他取代基取代。在本文中,多环意谓其中芳基直接连接至其他环状基团或与其他环状基团稠合的基团。在本文中,其他环状基团可为芳基,但亦可为不同类型的环状基团,诸如环烷基、杂环烷基以及杂芳基。芳基包含螺环基团。芳基的碳原子数可为6至60,特定言之6至40且更特定言之6至25。芳基的特定实例可包含苯基、联苯基、联三苯基、萘基、蒽基、屈基、菲基、苝基、芴蒽基、联亚三苯基、萉基、芘基、稠四苯基、稠五苯基、芴基、茚基、苊基、苯并芴基、螺联芴基、2,3-二氢-1H-茚基、其稠环以及类似基团,但不限于此。
在本说明书中,芴基可经取代,且相邻取代基可彼此结合以形成环。
在本说明书中,杂芳基包含作为杂原子的O、S、SO2、Se、N或Si,包含具有2个至60个碳原子的单环或多环,且可进一步经其他取代基取代。在本文中,多环意谓其中杂芳基直接连接至其他环状基团或与其他环状基团稠合的基团。在本文中,其他环状基团可为杂芳基,但亦可为不同类型的环状基团,诸如环烷基、杂环烷基以及芳基。杂芳基的碳原子数可为2至60,特定言之2至40且更特定言之3至25。杂芳基的特定实例可包含吡啶基、吡咯基、嘧啶基、哒嗪基、呋喃基、噻吩基、咪唑基、吡唑基、恶唑基、异恶唑基、噻唑基、异噻唑基、三唑基、呋吖基、恶二唑基、噻二唑基、二噻唑基、四唑基、哌喃基、硫代哌喃基、二嗪基(diazinylgroup)、恶嗪基、噻嗪基、二氧杂环己烯基(dioxynyl group)、三嗪基、四嗪基、喹啉基、异喹啉基、喹唑啉基、异喹唑啉基、喹嗪啉基(quinazolinyl group)、萘啶基(naphthyridylgroup)、吖啶基、啡啶基、咪唑并吡啶基、二氮杂萘基(diazanaphthalenyl group)、三吖茚基(triazaindene group)、吲哚基、吲哚嗪基、苯并噻唑基、苯并恶唑基、苯并咪唑基、苯并噻吩基、苯并呋喃基、二苯并噻吩基、二苯并呋喃基、咔唑基、苯并咔唑基、二苯并咔唑基、啡嗪基、二苯并硅杂环戊二烯基(dibenzosilole group)、螺二(二苯并硅杂环戊二烯)、二氢啡嗪基(dihydrophenazinyl group)、啡恶嗪基、菲啶基(phenanthridyl group)、咪唑并吡啶基、噻吩基、吲哚并[2,3-a]咔唑基、吲哚并[2,3-b]咔唑基、二氢吲哚基、10,11-二氢-二苯并[b,f]吖庚因、9,10-二氢吖啶基、菲嗪基(phenanthrazinyl group)、啡噻嗪基、酞嗪基、萘吲啶基(naphthylidinyl group)、啡啉并啉基、苯并[c][1,2,5]噻二唑基、5,10-二氢苯并[b,e][1,4]氮杂硅啉基、吡唑并[1,5-c]喹唑啉基、吡啶并[1,2-b]吲唑基、吡啶并[1,2-a]咪唑并[1,2-e]二氢吲哚基、苯并呋喃并[2,3-d]嘧啶基;苯并噻吩并[2,3-d]嘧啶基;苯并呋喃并[2,3-a]咔唑基、苯并噻吩并[2,3-a]咔唑基、1,3-二氢吲哚并[2,3-a]咔唑基、苯并呋喃并[3,2-a]咔唑基、苯并噻吩并[3,2-a]咔唑基、1,3-二氢吲哚并[3,2-a]咔唑基、苯并呋喃并[2,3-b]咔唑基、苯并噻吩并[2,3-b]咔唑基、1,3-二氢吲哚并[2,3-b]咔唑基、苯并呋喃并[3,2-b]咔唑基、苯并噻吩并[3,2-b]咔唑基、1,3-二氢吲哚并[3,2-b]咔唑基、苯并呋喃并[2,3-c]咔唑基、苯并噻吩并[2,3-c]咔唑基、1,3-二氢吲哚并[2,3-c]咔唑基、苯并呋喃并[3,2-c]咔唑基、苯并噻吩并[3,2-c]咔唑基、1,3-二氢吲哚并[3,2-c]咔唑基、1,3-二氢茚并[2,1-b]咔唑基、5,11-二氢茚并[1,2-b]咔唑基、5,12-二氢茚并[1,2-c]咔唑基、5,8-二氢茚并[2,1-c]咔唑基、7,12-二氢茚并[1,2-a]咔唑基、11,12-二氢茚并[2,1-a]咔唑基以及类似基团,但不限于此。
在本说明书中,硅基为包含Si、使Si原子直接连接作为自由基的取代基,且由-Si(R101)(R102)(R103)表示。R101至R103彼此相同或不同,且可各自独立地为由以下中的至少一者形成的取代基:氢;氘;卤基;烷基;烯基;烷氧基;环烷基;芳基;以及杂芳基。硅基的特定实例可包含三甲基硅基、三乙基硅基、第三丁基二甲基硅基、乙烯基二甲基硅基、丙基二甲基硅基、三苯基硅基、二苯基硅基、苯基硅基以及类似基团,但不限于此。
在本说明书中,氧化膦基团由-P(=O)(R104)(R105)表示,且R104及R105彼此相同或不同且可各自独立地为由以下中的至少一者形成的取代基:氢;氘;卤基;烷基;烯基;烷氧基;环烷基;芳基;以及杂芳基。特定言之,氧化膦基团可经芳基取代,且作为芳基,上文所描述的实例可适用。氧化膦基团的特定实例可包含氧化二苯基膦基、氧化二萘基膦基以及类似基团,但不限于此。
在本说明书中,胺基由-N(R106)(R107)表示,且R106及R107彼此相同或不同且可各自独立地为由以下中的至少一者形成的取代基:氢;氘;卤基;烷基;烯基;烷氧基;环烷基;芳基;以及杂芳基。胺基可由以下所组成的族群中选出:-NH2;单烷胺基;单芳胺基;单杂芳胺基;二烷胺基;二芳胺基;二杂芳胺基;烷基芳胺基;烷基杂芳胺基;以及芳基杂芳胺基,且尽管碳原子数不特定限制于此,但较佳为1至30。胺基的特定实例可包含甲胺基、二甲胺基、乙胺基、二乙胺基、苯胺基、萘胺基、联苯胺基、二联苯胺基、蒽胺基(anthracenylaminegroup)、9-甲基-蒽胺基、二苯胺基、苯基萘胺基、二甲苯胺基(ditolylamine group)、苯基甲苯胺基、三苯胺基、联苯萘胺基、苯基联苯胺基、联苯芴胺基、苯基亚三苯基胺基(phenyltriphenylenylamine group)、联苯亚三苯基胺基以及类似基团,但不限于此。
在本说明书中,除亚芳基为二价基团以外,上文所描述的芳基的实例可适用于亚芳基。
在本说明书中,除亚杂芳基为二价基团以外,上文所描述的杂芳基的实例可适用于亚杂芳基。
本说明书的一个实施例提供一种由化学式1表示的化合物。
在由化学式1表示的化合物中,联亚三苯的一个苯环经包含N的两个取代基(亦即,杂芳基及芳基)取代,且与具有仅经一个杂芳基取代的结构的化合物相比,HOMO轨域离域至芳基类取代基,从而有效地稳定空穴,且与具有仅经一个芳基取代的结构的化合物相比,获得更高的电子迁移率,从而导致装置使用寿命增强。通过用两个芳基取代联亚三苯的一个苯环作为另一结构,与具有仅经一个芳基取代的结构的化合物相比,HOMO轨域离域至两个取代基及联亚三苯,且可有效地稳定空穴。
在本说明书的一个实施例中,L1及L2各自独立地为直接键;经取代或未经取代的C6至C60亚芳基;或经取代或未经取代的C2至C60亚杂芳基。
在本说明书的一个实施例中,L1及L2各自独立地为直接键;经取代或未经取代的C6至C40亚芳基;或经取代或未经取代的C2至C40亚杂芳基。
在本说明书的一个实施例中,L1及L2各自独立地为直接键;经取代或未经取代的C6至C20亚芳基;或经取代或未经取代的C2至C20亚杂芳基。
在本说明书的一个实施例中,L1及L2各自独立地为直接键;经取代或未经取代的亚苯基;经取代或未经取代的亚联苯基;经取代或未经取代的联亚三苯基;经取代或未经取代的二价吡啶基;经取代或未经取代的二价嘧啶基;经取代或未经取代的二价三嗪基;或经取代或未经取代的二价咔唑基。
在本说明书的一个实施例中,L1及L2各自独立地为直接键;亚苯基;亚联苯基;联亚三苯基;未经取代或经芳基取代的二价吡啶基;未经取代或经芳基取代的二价嘧啶基;未经取代或经芳基取代的二价三嗪基;或二价咔唑基。
在本说明书的一个实施例中,Q1为经取代或未经取代的C6至C20芳基;或包含N的经取代或未经取代的C2至C20杂芳基。
在本说明书的一个实施例中,Q1为经取代或未经取代的苯基;经取代或未经取代的联苯基;经取代或未经取代的联三苯基;经取代或未经取代的萘基;经取代或未经取代的联亚三苯基;经取代或未经取代的吡啶基;经取代或未经取代的嘧啶基;经取代或未经取代的三嗪基;经取代或未经取代的苯并咪唑基;经取代或未经取代的喹唑啉基;经取代或未经取代的苯并呋喃并[2,3-d]嘧啶基;经取代或未经取代的苯并噻吩并[2,3-d]嘧啶基;或经取代或未经取代的菲咯啉基。
在本说明书的一个实施例中,Q1为苯基;联苯基;联三苯基;萘基;联亚三苯基;未经取代或经芳基取代的吡啶基;未经取代或经芳基取代的嘧啶基;未经取代或经芳基取代的三嗪基;未经取代或经芳基取代的苯并咪唑基;未经取代或经芳基取代的喹唑啉基;未经取代或经芳基取代的苯并呋喃并[2,3-d]嘧啶基;未经取代或经芳基取代的苯并噻吩并[2,3-d]嘧啶基;或菲咯啉基。
在本说明书的一个实施例中,Q2为氰基;经取代或未经取代的硅基;经取代或未经取代的胺基;经取代或未经取代的C1至C20烷基;经取代或未经取代的C6至C30芳基;经取代或未经取代的C2至C30杂芳基;或经取代或未经取代的氧化膦基团。
在本说明书的一个实施例中,Q2为氰基;经取代或未经取代的硅基;经取代或未经取代的胺基;经取代或未经取代的C1至C10烷基;经取代或未经取代的C6至C30芳基;经取代或未经取代的C2至C30杂芳基;或经取代或未经取代的氧化膦基团。
在本说明书的一个实施例中,Q2为氰基;经取代或未经取代的硅基;经取代或未经取代的胺基;经取代或未经取代的甲基;经取代或未经取代的苯基;经取代或未经取代的联苯基;经取代或未经取代的联三苯基;经取代或未经取代的萘基;经取代或未经取代的菲基;经取代或未经取代的联亚三苯基;经取代或未经取代的芘基;经取代或未经取代的芴基;经取代或未经取代的吡啶基;经取代或未经取代的嘧啶基;经取代或未经取代的三嗪基;经取代或未经取代的喹啉基;经取代或未经取代的喹唑啉基;经取代或未经取代的菲咯啉基;经取代或未经取代的咔唑基;经取代或未经取代的苯并咔唑基;经取代或未经取代的二苯并呋喃基;经取代或未经取代的二苯并噻吩基;经取代或未经取代的苯并咪唑基;未经取代或经芳基取代的氧化膦基团;或由以下结构式中选出。
在结构式中,
X、Y以及Z各自为O;S;C(R2)(R3);或N(R4),以及
R1至R4各自独立地为氢;氘;经取代或未经取代的C1至C10烷基;经取代或未经取代的C6至C20芳基;或经取代或未经取代的C2至C20杂芳基。
在本说明书的一个实施例中,Q2为氰基;未经取代或经芳基取代的硅基;未经取代或经芳基取代的胺基;未经取代或经芳基取代的甲基;未经取代或经氰基、芳基或杂芳基取代的苯基;联苯基;联三苯基;萘基;菲基;联亚三苯基;芘基;未经取代或经烷基或芳基取代的芴基;螺二芴基;未经取代或经芳基取代的吡啶基;未经取代或经芳基取代的嘧啶基;未经取代或经芳基或杂芳基取代的三嗪基;未经取代或经芳基取代的喹啉基;未经取代或经芳基取代的喹唑啉基;经取代或未经取代的菲咯啉基;未经取代或经芳基取代的咔唑基;苯并咔唑基;二苯并呋喃基;二苯并噻吩基;未经取代或经芳基取代的苯并咪唑基;未经取代或经芳基取代的氧化膦基团;或由以下结构式中选出的任一者。
在本说明书的一个实施例中,化学式1可由以下化学式1-1表示。
[化学式1-1]
在化学式1-1中,
各取代基具有与化学式1中相同的定义。
在本说明书的一个实施例中,当A2及A4为氢且Q1为未经取代或经芳基取代的三嗪基时,Q2为氰基;未经取代或经芳基取代的硅基;未经取代或经芳基取代的胺基;未经取代或经芳基取代的甲基;经取代或未经取代的苯基;经取代或未经取代的联苯基;经取代或未经取代的联三苯基;经取代或未经取代的萘基;经取代或未经取代的菲基;经取代或未经取代的联亚三苯基;经取代或未经取代的芘基;经取代或未经取代的芴基;经取代或未经取代的吡啶基;经取代或未经取代的嘧啶基;经取代或未经取代的三嗪基;经取代或未经取代的喹啉基;经取代或未经取代的喹唑啉基;经取代或未经取代的菲咯啉基;经取代或未经取代的咔唑基;经取代或未经取代的苯并咔唑基;经取代或未经取代的二苯并呋喃基;经取代或未经取代的二苯并噻吩基;经取代或未经取代的苯并咪唑基;经取代或未经取代的氧化膦基团;或由以下结构式中选出的任一者。
在本说明书的一个实施例中,当A2及A4为氢且Q1为未经取代或经芳基取代的吡啶基;未经取代或经芳基取代的嘧啶基;未经取代或经芳基取代的喹唑啉基;未经取代或经芳基取代的菲咯啉基;时,Q2为经取代或未经取代的苯基;经取代或未经取代的联苯基;经取代或未经取代的联三苯基;经取代或未经取代的联亚三苯基;经取代或未经取代的芴基;经取代或未经取代的二苯并呋喃基;经取代或未经取代的二苯并噻吩基;或经取代或未经取代的咔唑基。
在本说明书的一个实施例中,当A3及A4为氢时,Q1及Q2中的一者为未经取代或经芳基取代的三嗪基,且另一者为氰基;经取代或未经取代的苯基;经取代或未经取代的联苯基;经取代或未经取代的联三苯基;经取代或未经取代的萘基;经取代或未经取代的联亚三苯基;或经取代或未经取代的芴基。
在本说明书的一个实施例中,当A1及A4为氢时,Q1为未经取代或经芳基取代的三嗪基,且Q2为经取代或未经取代的硅基;经取代或未经取代的苯基;经取代或未经取代的联苯基;经取代或未经取代的联三苯基;经取代或未经取代的萘基;或经取代或未经取代的二苯并呋喃基。
在本说明书的一个实施例中,当A2及A3为氢时,Q1及Q2中的一者为未经取代或经芳基取代的三嗪基,且另一者为经取代或未经取代的联亚三苯基;或经取代或未经取代的咔唑基。
在本说明书的一个实施例中,当A1为(L1)a-Q1或(L2)b-Q2时,A4可为氢。
在本说明书的一个实施例中,当Q1及Q2皆为芳基时,满足以下中的一者:i)Q1及Q2皆为苯基,L1及L2为直接键,且A2及A4为氢;ii)Q1及Q2皆为苯基,L1及L2中的至少一者为经取代或未经取代的双环或低碳亚芳基;或经取代或未经取代的C2至C60亚杂芳基;以及iii)Q1及Q2中的至少一者为未经取代或经烷基或芳基取代的双环或高碳芳基。
在本说明书的一个实施例中,当Q1及Q2皆为芳基时,满足以下中的一者:i)Q1及Q2皆为苯基,L1及L2为直接键,且A2及A4为氢;ii)Q1及Q2皆为苯基,L1及L2中的至少一者为经取代或未经取代的双环或低碳亚芳基;或经取代或未经取代的C2至C60亚杂芳基;以及iii)Q1及Q2中的至少一者为联苯基;联三苯基;萘基;菲基;联亚三苯基;芘基;或经烷基或芳基取代的芴基。
在本说明书的一个实施例中,当Q1及Q2皆为芳基时,满足以下中的一者:i)Q1及Q2皆为苯基,L1及L2为直接键,且A2及A4为氢;ii)Q1及Q2皆为苯基,L1及L2中的至少一者为经取代或未经取代的双环或低碳亚芳基;或经取代或未经取代的C2至C60亚杂芳基;以及iii)Q1及Q2中的至少一者为联苯基;联三苯基;萘基;菲基;联亚三苯基;芘基;二甲基芴;或二苯基芴。
在本说明书的一个实施例中,由化学式1表示的化合物不包含蒽结构。
在本说明书的一个实施例中,化学式1可由以下化学式1-N或化学式1-P表示。
[化学式1-N]
在化学式1-N中,
A1至A4具有与化学式1中相同的定义,但包含至少一个杂芳基,所述杂芳基包含吡啶环、嘧啶环、三嗪环或咪唑环,
[化学式1-P]
在化学式1-P中,
A1至A4具有与化学式1中相同的定义,但不包含杂芳基,所述杂芳基包含吡啶环、嘧啶环、三嗪环或咪唑环。
特定言之,在化学式1的化合物中,包含杂芳基的化合物可由化学式1-N表示,所述杂芳基包含吡啶环、嘧啶环、三嗪环或咪唑环,且在化学式1的化合物中,不包含杂芳基的化合物可由化学式1-P表示,所述杂芳基包含吡啶环、嘧啶环、三嗪环或咪唑环。
在本说明书的一个实施例中,化学式1可由以下化合物中的任一者表示,但不限于此。
另外,通过将各种取代基引入至化学式1的结构,可合成具有所引入的取代基的独特特性的化合物。举例而言,通过将通常用作用于制造有机发光装置的空穴注入层材料、空穴传输层材料、发光层材料、电子传输层材料以及电荷产生层材料的取代基引入至核心结构,可合成满足各有机材料层所需条件的材料。
另外,通过将各种取代基引入至化学式1的结构,可精细控制能带隙,且同时,强化在有机材料之间的界面处的特性,且材料应用可变得多样化。
本说明书的一个实施例提供一种有机发光装置,其包含第一电极;第二电极;以及一或多个有机材料层,设置于第一电极与第二电极之间,其中有机材料层的一或多个层包含一或多种类型的由化学式1表示的化合物。
在本说明书的一个实施例中,有机材料层的一或多个层包含一种类型的由化学式1表示的化合物。
在另一实施例中,有机材料层的一或多个层包含两种类型的由化学式1表示的化合物。
在本说明书的一个实施例中,有机材料层还包含由以下化学式2表示的化合物。
[化学式2]
在化学式2中,
R21及R22各自独立地为经取代或未经取代的C1至C60烷基;经取代或未经取代的C3至C60环烷基;经取代或未经取代的C6至C60芳基;或经取代或未经取代的C2至C60杂芳基,
R23及R24各自独立地为氢;氘;经取代或未经取代的C1至C60烷基;经取代或未经取代的C3至C60环烷基;经取代或未经取代的C6至C60芳基;或经取代或未经取代的C2至C60杂芳基,
r及s各自为0至7的整数,以及
当r及s各自为2或大于2时,括弧中的取代基彼此相同或不同。
在本说明书的一个实施例中,化学式2可由以下化学式2-1至化学式2-4中的任一者表示。
[化学式2-1]
[化学式2-2]
[化学式2-3]
[化学式2-4]
在化学式2-1至化学式2-4中,
各取代基具有与化学式2中相同的定义。
在本说明书的一个实施例中,R21及R22各自独立地为经取代或未经取代的C1至C60烷基;经取代或未经取代的C3至C60环烷基;经取代或未经取代的C6至C60芳基;或经取代或未经取代的C2至C60杂芳基。
在本说明书的一个实施例中,R21及R22各自独立地为经取代或未经取代的C1至C40烷基;经取代或未经取代的C3至C40环烷基;经取代或未经取代的C6至C40芳基;或经取代或未经取代的C2至C40杂芳基。
在本说明书的一个实施例中,R21及R22各自独立地为经取代或未经取代的苯基;经取代或未经取代的联苯基;经取代或未经取代的联三苯基;经取代或未经取代的萘基;经取代或未经取代的联亚三苯基;经取代或未经取代的芴基;9,9'-螺二[芴];或经取代或未经取代的二苯并噻吩基。
在本说明书的一个实施例中,R21及R22各自独立地为经氰基或三苯基硅基取代的苯基;联苯基;联三苯基;萘基;联亚三苯基;未经取代或经甲基或苯基取代的芴基;9,9'-螺二[芴];或未经取代或经以下取代的二苯并噻吩基:苯基、联苯基、萘基、9,9-二甲基-9H-芴、二苯并呋喃基或二苯并噻吩基。
在本说明书的一个实施例中,R22为具有6个至30个碳原子的经取代或未经取代的芳基。
在本说明书的一个实施例中,R22为经取代或未经取代的苯基;经取代或未经取代的联苯基;经取代或未经取代的联三苯基;经取代或未经取代的萘基;经取代或未经取代的联亚三苯基;或经取代或未经取代的芴基。
在本说明书的一个实施例中,R22为经氰基或三苯基硅基取代的苯基;联苯基;联三苯基;萘基;联亚三苯基;或未经取代或经甲基或苯基取代的芴基。
在本说明书的一个实施例中,R23及R24各自独立地为氢;或氘。
在本说明书的一个实施例中,化学式2可由以下化合物中的任一者表示,但不限于此。
在本说明书的一个实施例中,第一电极可为阳极,且第二电极可为阴极。
在本说明书的另一实施例中,第一电极可为阴极,且第二电极可为阳极。
在本说明书的一个实施例中,有机发光装置可为蓝色有机发光装置,且由化学式1表示的化合物可用作蓝色有机发光装置的材料。举例而言,由化学式1表示的化合物可包含于蓝色有机发光装置的发光层中。
在本说明书的一个实施例中,有机发光装置可为绿色有机发光装置,且由化学式1表示的化合物可用作绿色有机发光装置的材料。举例而言,由化学式1表示的化合物可包含于绿色有机发光装置的发光层中。
在本说明书的一个实施例中,有机发光装置可为红色有机发光装置,且由化学式1表示的化合物可用作红色有机发光装置的材料。举例而言,由化学式1表示的化合物可包含于红色有机发光装置的发光层中。
除使用上文所描述的化合物形成有机材料层中的一或多者以外,可使用常用有机发光装置制造方法及材料来制造本说明书的有机发光装置。
当制造有机发光装置时,化合物可经由溶液涂布法以及真空沉积法形成为有机材料层。在本文中,溶液涂布法意谓旋涂、浸涂、喷墨印刷、网版印刷、喷涂法、滚涂以及类似方法,但不限于此。
本说明书的有机发光装置的有机材料层可以单层结构形成,但可以其中层压两个或大于两个有机材料层的多层结构形成。举例而言,本公开内容的有机发光装置可具有包含空穴注入层、空穴传输层、发光层、电子传输层、电子注入层以及类似层作为有机材料层的结构。然而,有机发光装置的结构不限于此,且可包含少量有机材料层。
在本说明书的有机发光装置中,有机材料层包含发光层,且发光层可包含一或多种类型的由化学式1表示的化合物。
在本说明书的有机发光装置中,有机材料层包含发光层,且发光层可包含一种类型的由化学式1表示的化合物。
在本说明书的有机发光装置中,有机材料层包含发光层,且发光层可包含两种类型的由化学式1表示的化合物。
在本说明书的有机发光装置中,有机材料层包含发光层,且发光层可包含由化学式1表示的化合物及由化学式2表示的化合物。
在本说明书的有机发光装置中,有机材料层包含发光层,发光层包含主体材料,且主体材料可包含由化学式1表示的化合物。
本公开内容的有机发光装置可还包含一个、两个或大于两个由以下所组成的族群中选出的层:发光层、空穴注入层、空穴传输层、电子注入层、电子传输层、电子阻挡层以及空穴阻挡层。
图1至图3示出根据本说明书的一个实施例的有机发光装置的电极及有机材料层的层压次序。然而,本申请案的范畴不限于此等附图,且所属领域中已知的有机发光装置的结构亦可用于本申请案中。
图1示出有机发光装置,其中阳极(200)、有机材料层(300)以及阴极(400)连续层压于基板(100)上。然而,所述结构不限于此类结构,且如图2中所示出,亦可获得其中阴极、有机材料层以及阳极连续层压于基板上的有机发光装置。
图3示出有机材料层为多层的情况。根据图3的有机发光装置包含空穴注入层(301)、空穴传输层(302)、发光层(303)、空穴阻挡层(304)、电子传输层(305)以及电子注入层(306)。然而,本申请案的范畴不限于此类层压结构,且视需要,可不包含除发光层以外的层,且可进一步增加其他必要功能层。
包含由化学式1表示的化合物的有机材料层可视需要还包含其他材料。
在根据本说明书的一个实施例的有机发光装置中,下文示出除由化学式1及化学式2表示的化合物以外的材料,然而,此等材料仅出于说明目的且不用于限制本申请案的范畴,且可由所属领域中已知的材料替代。
可使用具有相对较大功函数的材料作为阳极材料,且可使用透明的导电氧化物、金属、导电聚合物或类似材料作为阳极材料。阳极材料的特定实例包含金属,诸如钒、铬、铜、锌以及金,或其合金;金属氧化物,诸如氧化锌、氧化铟、氧化铟锡(indium tin oxide;ITO)以及氧化铟锌(indium zinc oxide;IZO);金属与氧化物的组合,诸如ZnO:Al或SnO2:Sb;导电聚合物,诸如聚(3-甲基噻吩)、聚[3,4-(乙烯-1,2-二氧基)噻吩](PEDOT)、聚吡咯以及聚苯胺及类似物,但不限于此。
可使用具有相对小功函数的材料作为阴极材料,且可使用金属、金属氧化物、导电聚合物或类似材料作为阴极材料。阴极材料的特定实例包含金属,诸如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡以及铅,或其合金;多层结构材料,诸如LiF/Al或LiO2/Al,以及类似材料,但不限于此。
可使用已知的空穴注入材料作为空穴注入材料,且例如可使用酞菁化合物,诸如美国专利第4,356,429号中所公开的铜酞菁;或星型(starburst-type)胺衍生物,诸如描述于文献[高级材料(Advanced Material),6,第677页(1994)]中的三(4-肼甲酰基-9-基苯基)胺(TCTA)、4,4',4"-三[苯基(间甲苯基)胺基]三苯胺(m-MTDATA)或1,3,5-三[4-(3-甲基苯基苯基胺基)苯基]苯(m-MTDAPB);作为具有溶解度的导电聚合物的聚苯胺/十二烷基苯磺酸、聚(3,4-乙烯二氧噻吩)/聚(4-苯乙烯磺酸酯)、聚苯胺/樟脑磺酸或聚苯胺/聚(4-苯乙烯磺酸酯);以及类似材料。
可使用吡唑啉衍生物、芳胺类衍生物、二苯乙烯衍生物、三苯基二胺衍生物以及类似材料作为空穴传输材料,且亦可使用低分子或高分子材料作为空穴传输材料。
可使用恶二唑衍生物的金属错合物、蒽醌二甲烷及其衍生物、苯醌及其衍生物、萘醌及其衍生物、蒽醌及其衍生物、四氰蒽醌二甲烷及其衍生物、芴酮衍生物、二苯基二氰乙烯及其衍生物、联苯醌衍生物、8-羟基喹啉及其衍生物以及类似材料作为电子传输材料,且亦可使用高分子材料以及低分子材料作为电子传输材料。
作为电子注入材料的实例,LiF通常用于所属领域中,然而,本申请案不限于此。
可使用红色、绿色或蓝色发光材料作为发光材料,且视需要可混合且使用两种或大于两种发光材料。在本文中,两种或大于两种发光材料可通过沉积为个别供应源或通过预混合且沉积为一个供应源而使用。另外,荧光材料亦可用作发光材料,然而,亦可使用磷光材料。可单独使用通过结合分别自阳极及阴极注入的电子及空穴来发光的材料作为发光材料,然而,亦可使用具有一起参与发光的主体材料及掺杂材料的材料作为发光材料。
当混合发光材料主体时,可混合相同系列主体,或可混合不同系列主体。举例而言,可选择n型主体材料或p型主体材料中的任何两种或大于两种类型的材料,且用作发光层的主体材料。
视所使用的材料而定,根据本说明书的一个实施例的有机发光装置可为顶部发光型、底部发光型或双面发光型。
根据本说明书的一个实施例的化合物亦可根据用于有机发光装置中的类似原理用于包含有机太阳能电池、有机光导体、有机晶体管以及类似物的有机电子装置中。
本说明书的一个实施例提供一种用于形成有机材料层的组成物,组成物包含a)由以下化学式N表示的化合物,及b)由以下化学式P或化学式2表示的化合物。
[化学式N]
[化学式P]
在化学式N及化学式P中,
A11至A14中的至少一者包含至少一个杂芳基,所述杂芳基包含吡啶环、嘧啶环、三嗪环或咪唑环,
A21至A24不包含杂芳基,所述杂芳基包含吡啶环、嘧啶环、三嗪环或咪唑环,
A11及A12中的一者为(L1)a-Q1,且A11及A12中的另一者以及A13及A14各自独立地为氢或(L2)b-Q2,且其至少一者为(L2)b-Q2,
A21及A22中的一者为(L1)a-Q1,A21及A22中的另一者以及A23及A24各自独立地为氢或(L2)b-Q2,且其至少一者为(L2)b-Q2,
a及b各自独立地为1至5的整数,
当a及b各自为2或大于2时,括弧中的取代基彼此相同或不同,
L1及L2各自独立地为直接键;经取代或未经取代的C6至C60亚芳基;或经取代或未经取代的C2至C60亚杂芳基,
Q1为经取代或未经取代的C6至C20芳基;或包含N的经取代或未经取代的C2至C20杂芳基,
Q2为氰基;经取代或未经取代的硅基;经取代或未经取代的胺基;经取代或未经取代的C1至C20烷基;经取代或未经取代的C6至C30芳基;经取代或未经取代的C2至C30杂芳基;或经取代或未经取代的氧化膦基团,
当A12及A13为氢时,Q1为苯基且Q2包含吡啶或三嗪,L1为经取代或未经取代的C6至C60亚芳基;或经取代或未经取代的C2至C60亚杂芳基,以及
当Q1及Q2皆为芳基时,满足以下中的一者:i)Q1及Q2皆为苯基,L1及L2为直接键,且A2及A4为氢;ii)Q1及Q2皆为苯基,L1及L2中的至少一者为经取代或未经取代的双环或低碳亚芳基;或经取代或未经取代的C2至C60亚杂芳基;以及iii)Q1及Q2中的至少一者为未经取代或经烷基或芳基取代的双环或高碳芳基,
[化学式2]
在化学式2中,
R21及R22各自独立地为经取代或未经取代的C1至C60烷基;经取代或未经取代的C3至C60环烷基;经取代或未经取代的C6至C60芳基;或经取代或未经取代的C2至C60杂芳基,
R23及R24各自独立地为氢;氘;经取代或未经取代的C1至C60烷基;经取代或未经取代的C3至C60环烷基;经取代或未经取代的C6至C60芳基;或经取代或未经取代的C2至C60杂芳基,
r及s各自为0至7的整数,以及
当r及s各自为2或大于2时,括弧中的取代基彼此相同或不同。
用于形成根据本说明书的一个实施例的有机材料层的组成物可以1:10至10:1、1:8至8:1、1:5至5:1或1:2至2:1的重量比包含a)由化学式N表示的化合物及b)由化学式P或化学式2表示的化合物,且重量比可较佳为1:2。
在本说明书中,化学式N与化学式1-N相同,且化学式P与化学式1-P相同。
在下文中,本说明书将参考实例更详细地进行描述,然而,此等仅出于说明目的,且本申请案的范畴不限于此。
<制备实例>
<制备实例1>制备化合物1-1
1)制备化合物1-1-4
在将1-溴-2-氯-4-碘苯(18.2克,57.4毫摩尔浓度)、苯基硼酸(7.7克,63.1毫摩尔浓度)、Pd(PPh3)4(四(三苯基膦)钯(0))(3.3克,2.9毫摩尔浓度)以及K2CO3(15.9克,114.8毫摩尔浓度)溶解于1,4-二恶烷/H2O(200毫升/40毫升)中之后,将所得物回流24小时。在反应完成之后,通过在室温下向其中引入蒸馏水及二氯甲烷(DCM)来萃取所得物,且在用MgSO4干燥有机层之后,使用旋转蒸发器移除溶剂。反应材料通过管柱层析(DCM:己烷(Hex)=1:10)纯化以获得化合物1-1-4(12.3克,80%)。
2)制备化合物1-1-3
在将化合物1-1-4(10克,37.4毫摩尔浓度)、(2'-溴-[1,1'-联苯]-2-基)硼酸(10.4克,37.4毫摩尔浓度)、Pd(PPh3)4(2.2克,1.9毫摩尔浓度)以及K2CO3(10.3克,74.8毫摩尔浓度)溶解于1,4-二恶烷/H2O(200毫升/40毫升)中之后,将所得物回流24小时。在反应完成之后,通过在室温下向其中引入蒸馏水及DCM来萃取所得物,且在用MgSO4干燥有机层之后,使用旋转蒸发器移除溶剂。反应材料通过管柱层析(DCM:Hex=1:10)纯化以获得化合物1-1-3(13.3克,85%)。
3)制备化合物1-1-2
在将化合物1-1-3(11.6克,27.7毫摩尔浓度)、Pd(OAc)2(乙酸钯(II))(622毫克,2.8毫摩尔浓度)、PCy3·HBF4(三环己基膦四氟硼酸盐)(2.0克,5.5毫摩尔浓度)以及K2CO3(7.7克,55.4毫摩尔浓度)溶解于N,N-二甲基甲酰胺(DMF)(100毫升)中之后,将所得物回流12小时。在反应完成之后,通过在室温下向其中引入蒸馏水及DCM来萃取所得物,且在用MgSO4干燥有机层之后,使用旋转蒸发器移除溶剂。反应材料通过管柱层析(DCM:Hex=1:10)纯化以获得化合物1-1-2(6.6克,70%)。
4)制备化合物1-1-1
在将化合物1-1-2(6.5克,19.2毫摩尔浓度)、双(频哪醇)二硼(7.3克,28.8毫摩尔浓度)、Pd2(dba)3(三(二苯亚甲基丙酮)二钯(0))(879毫克,1.0毫摩尔浓度)、Xphos(2-二环己基膦-2',4',6'-三异丙基联苯)(915毫克,1.9毫摩尔浓度)以及KOAc(乙酸钾)(5.6克,57.3毫摩尔浓度)于1,4-二恶烷(100毫升)中之后,将所得物回流24小时。在反应完成之后,通过在室温下向其中引入蒸馏水及DCM来萃取所得物,且在用MgSO4干燥有机层之后,使用旋转蒸发器移除溶剂。反应材料通过管柱层析(DCM:Hex=1:3)纯化,且用甲醇再结晶以获得化合物1-1-1(7克,85%)。
5)制备化合物1-1
在将化合物1-1-1(6.9克,16.1毫摩尔浓度)、2-氯-4,6-二苯基-1,3,5-三嗪(4.7克,17.7毫摩尔浓度)、Pd(PPh3)4(0.9克,0.8毫摩尔浓度)以及K2CO3(4.5克,32.3毫摩尔浓度)溶解于1,4-二恶烷/H2O(200毫升/40毫升)中之后,将所得物回流24小时。在反应完成之后,通过在室温下向其中引入蒸馏水及DCM来萃取所得物,且在用MgSO4干燥有机层之后,使用旋转蒸发器移除溶剂。反应材料通过管柱层析(DCM:Hex=1:3)纯化,且用甲醇再结晶以获得目标化合物1-1(7.1克,82%)。
除了使用下表1的中间物A代替苯基硼酸,且使用下表1的中间物B代替2-氯-4,6-二苯基-1,3,5-三嗪以外,以与制备实例1中相同的方式合成目标化合物A。
[表1]
除了使用下表2的中间物C代替1-溴-2-氯-4-碘苯,使用中间物D代替苯基硼酸,且使用中间物E代替2-氯-4,6-二苯基-1,3,5-三嗪以外,以与制备实例1中相同的方式合成目标化合物A。
[表2]
<制备实例2>合成化合物3-3
1)制备化合物3-3
在将3-溴-1,1'-联苯(3.7克,15.8毫摩尔浓度)、9-苯基-9H,9'H-3,3'-二咔唑(6.5克,15.8毫摩尔浓度)、CuI(3.0克,15.8毫摩尔浓度)、反式-1,2-二胺基环己烷(1.9毫升,15.8毫摩尔浓度)以及K3PO4(3.3克,31.6毫摩尔浓度)溶解于1,4-二恶烷(100毫升)中之后,将所得物回流24小时。在反应完成之后,通过在室温下向其中引入蒸馏水及DCM来萃取所得物,且在用MgSO4干燥有机层之后,使用旋转蒸发器移除溶剂。反应材料通过管柱层析(DCM:Hex=1:3)纯化,且用甲醇再结晶以获得目标化合物3-3(7.5克,85%)。
除了使用下表3的中间物F代替3-溴-1,1'-联苯,且使用下表3的中间物G代替9-苯基-9H,9'H-3,3'-二咔唑以外,以与制备实例2中相同的方式合成目标化合物B。
[表3]
<制备实例3>合成化合物4-2
1)制备化合物4-2-2
在将2-溴二苯并[b,d]噻吩(4.2克,15.8毫摩尔浓度)、9-苯基-9H,9'H-3,3'-二咔唑(6.5克,15.8毫摩尔浓度)、CuI(3.0克,15.8毫摩尔浓度)、反式-1,2-二胺基环己烷(1.9毫升,15.8毫摩尔浓度)以及K3PO4(3.3克,31.6毫摩尔浓度)溶解于1,4-二恶烷(100毫升)中之后,将所得物回流24小时。在反应完成之后,通过在室温下向其中引入蒸馏水及DCM来萃取所得物,且在用MgSO4干燥有机层之后,使用旋转蒸发器移除溶剂。反应材料通过管柱层析(DCM:Hex=1:3)纯化,且用甲醇再结晶以获得目标化合物4-2-2(7.9克,85%)。
2)制备化合物4-2-1
在-78℃下,向通过引入化合物4-2-2(8.4克,14.3毫摩尔)及四氢呋喃(THF)(100毫升)而获得的混合物溶液中逐滴添加2.5摩尔浓度n-BuLi(7.4毫升,18.6毫摩尔),且将所得物在室温下搅拌1小时。向反应混合物中逐滴添加硼酸三甲酯(B(OMe)3)(4.8毫升,42.9毫摩尔),且将所得物在室温下搅拌2小时。在反应完成之后,通过在室温下向其中引入蒸馏水及DCM来萃取所得物,且在用MgSO4干燥有机层之后,使用旋转蒸发器移除溶剂。反应材料通过管柱层析(DCM:MeOH=100:3)纯化,且用DCM再结晶以获得目标化合物4-2-1(3.9克,70%)。
3)制备化合物4-2
在将化合物4-2-1(6.7克,10.5毫摩尔浓度)、碘苯(2.1克,10.5毫摩尔浓度)、Pd(PPh3)4(606毫克,0.52毫摩尔浓度)以及K2CO3(2.9克,21.0毫摩尔浓度)溶解于甲苯/EtOH/H2O(100毫升/20毫升/20毫升)中之后,将所得物回流12小时。在反应完成之后,通过在室温下向其中引入蒸馏水及DCM来萃取所得物,且在用MgSO4干燥有机层之后,使用旋转蒸发器移除溶剂。反应材料通过管柱层析(DCM:Hex=1:3)纯化,且用甲醇再结晶以获得目标化合物4-2(4.9克,70%)。
<制备实例4>合成化合物4-3
除了使用4-碘-1,1'-联苯代替碘苯以外,以与制备实例3的化合物4-2的制备中相同的方式获得目标化合物4-3(83%)
<制备实例5>合成化合物4-12
除了使用4-碘二苯并[b,d]呋喃代替碘苯以外,以与制备实例3的化合物4-2的制备中相同的方式获得目标化合物4-12(80%)。
亦以与上文所描述的制备实例中相同的方式制备除了制备实例1至制备实例5及表1至表3中所描述的化合物以外的化合物。
上文所制备的化合物的合成结果展示于下表4及表5中。
[表4]
[表5]
化合物 | FD-MS | 化合物 | FD-MS |
1-1 | m/z=535.20(C<sub>39</sub>H<sub>25</sub>N<sub>3</sub>=535.65) | 1-4 | m/z=611.24(C<sub>45</sub>H<sub>29</sub>N<sub>3</sub>=611.75) |
1-7 | m/z=687.27(C<sub>51</sub>H<sub>33</sub>N<sub>3</sub>=687.85) | 1-8 | m/z=687.27(C<sub>51</sub>H<sub>33</sub>N<sub>3</sub>=687.85) |
1-9 | m/z=763.30(C<sub>57</sub>H<sub>37</sub>N<sub>3</sub>=763.94) | 1-17 | m/z=685.25(C<sub>51</sub>H<sub>31</sub>N<sub>3</sub>=685.83) |
1-21 | m/z=761.28(C<sub>57</sub>H<sub>35</sub>N<sub>3</sub>=761.93) | 1-27 | m/z=625.22(C<sub>45</sub>H<sub>27</sub>N<sub>3</sub>O=625.73) |
1-28 | m/z=625.22(C<sub>45</sub>H<sub>27</sub>N<sub>3</sub>O=625.73) | 1-31 | m/z=641.19(C<sub>45</sub>H<sub>27</sub>N<sub>3</sub>S=641.79) |
1-34 | m/z=651.27(C<sub>48</sub>H<sub>33</sub>N<sub>3</sub>=651.81) | 1-39 | m/z=700.26(C<sub>51</sub>H<sub>32</sub>N<sub>4</sub>=700.84) |
1-44 | m/z=793.29(C<sub>57</sub>H<sub>39</sub>N<sub>3</sub>Si=794.04) | 1-46 | m/z=560.20(C<sub>40</sub>H<sub>24</sub>N<sub>4</sub>=560.66) |
1-49 | m/z=717.22(C<sub>51</sub>H<sub>31</sub>N<sub>3</sub>S=717.89) | 1-56 | m/z=865.32(C<sub>63</sub>H<sub>39</sub>N<sub>5</sub>=866.04) |
1-90 | m/z=686.27(C<sub>52</sub>H<sub>34</sub>N<sub>2</sub>=686.86) | 1-92 | m/z=736.29(C<sub>56</sub>H<sub>36</sub>N<sub>2</sub>=736.92) |
1-99 | m/z=535.20(C<sub>39</sub>H<sub>25</sub>N<sub>3</sub>=535.65) | 1-101 | m/z=611.24(C<sub>45</sub>H<sub>29</sub>N<sub>3</sub>=611.75) |
1-108 | m/z=685.25(C<sub>51</sub>H<sub>31</sub>N<sub>3</sub>=685.83) | 1-121 | m/z=611.24(C<sub>45</sub>H<sub>29</sub>N<sub>3</sub>=611.75) |
1-122 | m/z=611.24(C<sub>45</sub>H<sub>29</sub>N<sub>3</sub>=611.75) | 1-127 | m/z=761.28(C<sub>57</sub>H<sub>35</sub>N<sub>3</sub>=761.93) |
2-7 | m/z=532.22(C<sub>42</sub>H<sub>28</sub>=532.69) | 2-17 | m/z=530.20(C<sub>42</sub>H<sub>26</sub>=530.67) |
2-22 | m/z=606.23(C<sub>48</sub>H<sub>30</sub>=606.77) | 2-27 | m/z=470.17(C<sub>36</sub>H<sub>22</sub>O=470.57) |
2-31 | m/z=486.14(C<sub>36</sub>H<sub>22</sub>S=486.63) | 2-39 | m/z=545.21(C<sub>42</sub>H<sub>27</sub>N=545.68) |
2-42 | m/z=620.25(C<sub>49</sub>H<sub>32</sub>=620.25) | 2-44 | m/z=638.24(C<sub>48</sub>H<sub>34</sub>Si=638.89) |
2-56 | m/z=710.27(C<sub>54</sub>H<sub>34</sub>N<sub>2</sub>=710.88) | 2-70 | m/z=699.29(C<sub>54</sub>H<sub>37</sub>N=699.90) |
2-72 | m/z=786.30(C<sub>60</sub>H<sub>38</sub>N<sub>2</sub>=786.98) | 2-80 | m/z=680.25(C<sub>54</sub>H<sub>32</sub>=680.85) |
3-3 | m/z=560.23(C<sub>42</sub>H<sub>28</sub>N<sub>2</sub>=560.70) | 3-4 | m/z=560.23(C<sub>42</sub>H<sub>28</sub>N<sub>2</sub>=560.70) |
3-7 | m/z=636.26(C<sub>48</sub>H<sub>32</sub>N<sub>2</sub>=636.80) | 3-31 | m/z=636.26(C<sub>48</sub>H<sub>32</sub>N<sub>2</sub>=636.80) |
3-32 | m/z=636.26(C<sub>48</sub>H<sub>32</sub>N<sub>2</sub>=636.80) | 4-2 | m/z=666.84(C<sub>48</sub>H<sub>30</sub>N<sub>2</sub>=666.21) |
4-3 | m/z=742.24(C<sub>54</sub>H<sub>34</sub>N<sub>2</sub>S=742.94) | 4-12 | m/z=756.22(C<sub>54</sub>H<sub>32</sub>N<sub>2</sub>OS=756.92) |
<实验实例1>
1)制造有机发光装置
用蒸馏水超音波清洗其上涂布有厚度为1,500埃的氧化铟锡(ITO)薄膜的玻璃基板。在用蒸馏水清洗完成之后,用溶剂(诸如丙酮、甲醇以及异丙醇)超音波清洗基板,接着干燥,且在紫外线(ultraviolet;UV)清洁器中使用UV进行紫外线臭氧(ultravioletozone;UVO)处理5分钟。此后,将基板转移至等离子体清洁器(plasma cleaner;PT),且在真空下进行等离子体处理供用于ITO功函数及残余膜移除之后,将基板转移至热沉积设备供用于有机沉积。
在透明ITO电极(阳极)上,形成作为常用层的空穴注入层2-TNATA(4,4',4"-三[2-萘基(苯基)胺基]三苯胺)及空穴传输层NPB(N,N'-二(1-萘基)-N,N'-二苯基-(1,1'-联苯)-4,4'-二胺)。
如下在其上热真空沉积发光层。作为发光层,沉积400埃的下表6中描述的发光层化合物(化学式1的化合物、化学式2的化合物或参考物1至参考物5)作为主体,且作为绿色磷光掺杂剂,相对于发光层的沉积厚度掺杂且沉积7%的Ir(ppy)3。此后,沉积60埃的BCP(浴铜灵(bathocuproine))作为空穴阻挡层,且在其上沉积200埃的Alq3作为电子传输层。最后,通过沉积厚度为10埃的氟化锂(LiF)而在电子传输层上形成电子注入层,且接着通过沉积厚度为1,200埃的铝(Al)阴极而在电子注入层上形成阴极,且因此,制造有机电致发光装置。
同时,在10-8托至10-6托下,针对OLED制造中使用的各材料真空升华纯化所有制造OLED所需的有机化合物。
2)评估有机发光装置
对于如上所制造的有机电致发光装置中的每一者,使用由麦克科学公司(McScience Inc.)制造的M7000来测量电致发光(electroluminescent;EL)特性,且通过所述测量结果,当标准亮度为6,000坎德拉/平方米时,经由由麦克科学公司制造的使用寿命测量系统(M6000)来测量T90。
测量根据本公开内容制造的有机发光装置的驱动电压、发光效率、色彩坐标(color coordinate;CIE)以及使用寿命的结果如下表6中所展示。
[表6]
如自表6的结果所见,已确定,与比较实例1至比较实例11相比,使用本公开内容的有机电致发光装置的发光层材料的有机电致发光装置具有更低的驱动电压、增强的发光效率以及显著提高的使用寿命。
根据本公开内容的化合物1-7的HOMO轨域离域至联亚三苯及芳基类取代基。然而,已确定,当在参考物1及参考物3的化合物中的联亚三苯基中不存在芳基类取代基时,HOMO定域至联亚三苯,从而未能有效地稳定空穴,且由此降低使用寿命。
已确定,当在参考物2及参考物4的化合物中的联亚三苯基中不存在三嗪时,电子迁移率降低且空穴与电子之间的平衡在发光层中破裂,且由此降低使用寿命。
化合物2-7的HOMO轨域离域至联亚三苯及两个取代基,即苯基及联三苯基,其能够有效地稳定空穴。然而,已确定,当在参考物4的化合物中的联亚三苯基中存在一个取代基时,HOMO轨域相对地定域,从而未能有效地稳定空穴,且由此降低使用寿命。
参考物5的化合物具有与本揭示内容的化合物相同的取代位置,然而,具有结合至其上的蒽取代基。在此化合物中,HOMO及LUMO轨域皆定域至蒽。已确定,与HOMO及LUMO轨域共轭时相比,此降低空穴及电子的稳定性,且由此降低使用寿命。
<实验实例2>
1)制造有机发光装置
用蒸馏水超音波清洗其上涂布有厚度为1,500埃的氧化铟锡(ITO)薄膜的玻璃基板。在用蒸馏水清洗完成之后,用溶剂(诸如丙酮、甲醇以及异丙醇)超音波清洗基板,接着干燥,且在紫外线(UV)清洁器中使用UV进行紫外线臭氧(UVO)处理5分钟。此后,将基板转移至等离子体清洁器(PT),且在真空下进行等离子体处理供用于ITO功函数及残余膜移除之后,将基板转移至热沉积设备供用于有机沉积。
在透明ITO电极(阳极)上,形成作为常用层的空穴注入层2-TNATA(4,4',4"-三[2-萘基(苯基)胺基]三苯胺)及空穴传输层NPB(N,N'-二(1-萘基)-N,N'-二苯基-(1,1'-联苯)-4,4'-二胺)。
如下在其上热真空沉积发光层。作为发光层,将一种类型的化学式1-N的化合物及一种类型的化学式1-P的化合物(实例40至实例46)、一种类型的化学式1-N的化合物及一种类型的化学式2的化合物(实例47至实例67)或一种类型的化学式1-N的化合物及参考物6(比较实例12至比较实例14)预混合且接着在一个供应源中沉积至400埃作为如下表7中所描述的主体,且相对于发光层的沉积厚度掺杂且沉积7%的量的Ir(ppy)3作为绿色磷光掺杂剂。此后,沉积60埃的BCP(浴铜灵)作为空穴阻挡层,且在其上沉积200埃的Alq3作为电子传输层。最后,通过沉积厚度为10埃的氟化锂(LiF)而在电子传输层上形成电子注入层,且接着通过沉积厚度为1,200埃的铝(Al)阴极而在电子注入层上形成阴极,且因此,制造有机电致发光装置。
同时,在10-8托至10-6托下,针对OLED制造中使用的各材料真空升华纯化所有制造OLED所需的有机化合物。
2)评估有机发光装置
对于如上所制造的有机电致发光装置中的每一者,使用由麦克科学公司制造的M7000来测量电致发光(EL)特性,且通过所述测量结果,当标准亮度为6,000坎德拉/平方米时,经由由麦克科学公司制造的使用寿命测量系统(M6000)来测量T90。
测量根据本公开内容制造的有机发光装置的驱动电压、发光效率、色彩坐标(CIE)以及使用寿命的结果如下表7中所展示。
[表7]
如自表7的结果所见,当包含化学式1-N的化合物及化学式1-P的化合物两者,或化学式1-N的化合物及化学式2的化合物两者时,获得更优良的效率及使用寿命的效果。此类结果可导致预测当同时包含两种化合物时会发生激发复合物(exciplex)现象。
激发复合物现象是由于两个分子之间的电子交换而释放具有供体(p主体)HOMO级别大小及受体(n主体)LUMO级别大小的能量的现象。当在两个分子之间发生激发复合物现象时,发生反向系统间穿越(reverse intersystem crossing;RISC),且因此,荧光的内部量子效率可增加至高达100%。当使用具有良好空穴传输能力的供体(p主体)及具有良好电子传输能力的受体(n主体)作为发光层的主体时,将空穴注入至p主体且将电子注入至n主体,且因此,驱动电压可降低,因而有助于增强使用寿命。在本申请案的发明中,已确定,当使用起供体作用的化学式1-P的化合物或化学式2的化合物及起受体作用的化学式1-N的化合物作为发光层主体时,获得极佳的装置特性。
Claims (15)
1.一种化合物,由以下化学式1表示:
[化学式1]
其中,在化学式1中,
A1及A2中的一者为(L1)a-Q1;
A1及A2中的另一者及A3以及A4各自独立地为氢;氘;或(L2)b-Q2,且其至少一者为(L2)b-Q2;
a及b各自独立地为1至5的整数;
当a及b各自为2或大于2时,括弧中的取代基彼此相同或不同;
L1及L2各自独立地为直接键;经取代或未经取代的C6至C60亚芳基;或经取代或未经取代的C2至C60亚杂芳基;
Q1为经取代或未经取代的C6至C20芳基;或包含N的经取代或未经取代的C2至C20杂芳基;
Q2为氰基;经取代或未经取代的硅基;经取代或未经取代的胺基;经取代或未经取代的C1至C20烷基;经取代或未经取代的C6至C30芳基;经取代或未经取代的C2至C30杂芳基;或经取代或未经取代的氧化膦基团;
当A2及A3为氢时,Q1为苯基且Q2包含吡啶或三嗪,L1为经取代或未经取代的C6至C60亚芳基;或经取代或未经取代的C2至C60亚杂芳基;以及
当Q1及Q2皆为芳基时,满足以下中的一者:i)Q1及Q2皆为苯基,L1及L2为直接键,且A2及A4为氢;ii)Q1及Q2皆为苯基,L1及L2中的至少一者为经取代或未经取代的双环或低碳亚芳基;或经取代或未经取代的C2至C60亚杂芳基;以及iii)Q1及Q2中的至少一者为未经取代或经烷基或芳基取代的双环或高碳芳基。
3.根据权利要求1所述的化合物,其中L1及L2各自独立地为直接键;经取代或未经取代的亚苯基;经取代或未经取代的亚联苯基;经取代或未经取代的联亚三苯基;经取代或未经取代的二价吡啶基;经取代或未经取代的二价嘧啶基;经取代或未经取代的二价三嗪基;或经取代或未经取代的二价咔唑基。
4.根据权利要求1所述的化合物,其中Q2为氰基;未经取代或经芳基取代的硅基;未经取代或经芳基取代的胺基;经芳基取代的C1至C20烷基;未经取代或经氰基、烷基、芳基或杂芳基取代的C6至C30芳基;未经取代或经烷基、芳基或杂芳基取代的C2至C30杂芳基;或未经取代或经芳基取代的氧化膦基团。
6.一种有机发光装置,包括:
第一电极;
第二电极;以及
有机材料层,设置于所述第一电极与所述第二电极之间,
其中所述有机材料层包含一种或多种类型的如权利要求1至5中任一项所述的化合物。
7.根据权利要求6所述的有机发光装置,其中所述有机材料层包含两种类型的所述化合物。
10.根据权利要求6所述的有机发光装置,其中所述有机材料层包含发光层,且所述发光层包含一种或多种类型的所述化合物。
11.根据权利要求6所述的有机发光装置,其中所述有机材料层包含发光层,所述发光层包含主体材料,且所述主体材料包含一种或多种类型的所述化合物。
12.根据权利要求6所述的有机发光装置,其中所述有机材料层包含发光层,所述发光层包含主体材料,且所述主体材料包含所述化合物及以下化学式2的化合物:
[化学式2]
在化学式2中,
R21及R22各自独立地为经取代或未经取代的C1至C60烷基;经取代或未经取代的C3至C60环烷基;经取代或未经取代的C6至C60芳基;或经取代或未经取代的C2至C60杂芳基;
R23及R24各自独立地为氢;氘;经取代或未经取代的C1至C60烷基;经取代或未经取代的C3至C60环烷基;经取代或未经取代的C6至C60芳基;或经取代或未经取代的C2至C60杂芳基;
r及s各自为0至7的整数;以及
当r及s各自为2或大于2时,括弧中的取代基彼此相同或不同。
13.根据权利要求6所述的有机发光装置,还包括由以下所组成的族群中选出的一个层:发光层、空穴注入层、空穴传输层、电子注入层、电子传输层、电子阻挡层以及空穴阻挡层。
14.一种用于形成有机材料层的组成物,所述组成物包括:
a)以下化学式N的化合物;以及
b)以下化学式P或化学式2的化合物:
[化学式N]
[化学式P]
其中,在化学式N及化学式P中,
A11至A14中的至少一者包含至少一个杂芳基,所述杂芳基包含吡啶环、嘧啶环、三嗪环或咪唑环;
A21至A24不包含杂芳基,所述杂芳基包含吡啶环、嘧啶环、三嗪环或咪唑环;
A11及A12中的一者为(L1)a-Q1,A11及A12中的另一者以及A13及A14各自独立地为氢或(L2)b-Q2,且其至少一者为(L2)b-Q2;
A21及A22中的一者为(L1)a-Q1,A21及A22中的另一者以及A23及A24各自独立地为氢或(L2)b-Q2,且其至少一者为(L2)b-Q2;
a及b各自独立地为1至5的整数;
当a及b各自为2或大于2时,括弧中的取代基彼此相同或不同;
L1及L2各自独立地为直接键;经取代或未经取代的C6至C60亚芳基;或经取代或未经取代的C2至C60亚杂芳基;
Q1为经取代或未经取代的C6至C20芳基;或包含N的经取代或未经取代的C2至C20杂芳基;
Q2为氰基;经取代或未经取代的硅基;经取代或未经取代的胺基;经取代或未经取代的C1至C20烷基;经取代或未经取代的C6至C30芳基;经取代或未经取代的C2至C30杂芳基;或经取代或未经取代的氧化膦基团;
当A12及A13为氢时,Q1为苯基且Q2包含吡啶或三嗪,L1为经取代或未经取代的C6至C60亚芳基;或经取代或未经取代的C2至C60亚杂芳基;以及
当Q1及Q2皆为芳基时,满足以下中的一者:i)Q1及Q2皆为苯基,L1及L2为直接键,且A2及A4为氢;ii)Q1及Q2皆为苯基,L1及L2中的至少一者为经取代或未经取代的双环或低碳亚芳基;或经取代或未经取代的C2至C60亚杂芳基;以及iii)Q1及Q2中的至少一者为未经取代或经烷基或芳基取代的双环或高碳芳基,
[化学式2]
在化学式2中,
R21及R22各自独立地为经取代或未经取代的C1至C60烷基;经取代或未经取代的C3至C60环烷基;经取代或未经取代的C6至C60芳基;或经取代或未经取代的C2至C60杂芳基;
R23及R24各自独立地为氢;氘;经取代或未经取代的C1至C60烷基;经取代或未经取代的C3至C60环烷基;经取代或未经取代的C6至C60芳基;或经取代或未经取代的C2至C60杂芳基;
r及s各自为0至7的整数;以及
当r及s各自为2或大于2时,括弧中的取代基彼此相同或不同。
15.根据权利要求14所述的用于形成有机材料层的组成物,其中a)所述化学式N的化合物及b)所述化学式P或化学式2的化合物具有1:10至10:1的重量比。
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