WO2018217067A1 - Phosphorescent host composition, organic optoelectronic diode, and display device - Google Patents
Phosphorescent host composition, organic optoelectronic diode, and display device Download PDFInfo
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- WO2018217067A1 WO2018217067A1 PCT/KR2018/005989 KR2018005989W WO2018217067A1 WO 2018217067 A1 WO2018217067 A1 WO 2018217067A1 KR 2018005989 W KR2018005989 W KR 2018005989W WO 2018217067 A1 WO2018217067 A1 WO 2018217067A1
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- SRPUGGXXVCXONJ-UHFFFAOYSA-N CC1(C)C2=C(C=C(C=C2)N(C2=CC=C(C=C2)C2=CC=CC=C2)C2=CC=C(C=C2)C2=CC=CC=C2)C2=C1C=CC1=C2OC2=C1C=CC=C2 Chemical compound CC1(C)C2=C(C=C(C=C2)N(C2=CC=C(C=C2)C2=CC=CC=C2)C2=CC=C(C=C2)C2=CC=CC=C2)C2=C1C=CC1=C2OC2=C1C=CC=C2 SRPUGGXXVCXONJ-UHFFFAOYSA-N 0.000 description 1
- HTPBLQHMIWDOAH-RRQHEKLDSA-N CCC(C)[C@H]1C(CN)C1 Chemical compound CCC(C)[C@H]1C(CN)C1 HTPBLQHMIWDOAH-RRQHEKLDSA-N 0.000 description 1
- PNCHFEDLXLZAKQ-UHFFFAOYSA-N CCc(cc1)ccc1-c1nc(-c(cc2)ccc2-c2ccccc2)nc(-c2c(c3ccccc3[o]3)c3ccc2)n1 Chemical compound CCc(cc1)ccc1-c1nc(-c(cc2)ccc2-c2ccccc2)nc(-c2c(c3ccccc3[o]3)c3ccc2)n1 PNCHFEDLXLZAKQ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- BQHRJUASXACWDG-UHFFFAOYSA-N ClN1NC(=CC(=N1)Cl)C1=CC=CC=C1 Chemical compound ClN1NC(=CC(=N1)Cl)C1=CC=CC=C1 BQHRJUASXACWDG-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- MGKWYRSLGCEEHX-DBICJICXSA-N N=C(c1cccc2c1[o]c1c2cccc1)/N=C(/c1cc2ccccc2cc1)\N=C\c(cc1)ccc1-c1ccccc1 Chemical compound N=C(c1cccc2c1[o]c1c2cccc1)/N=C(/c1cc2ccccc2cc1)\N=C\c(cc1)ccc1-c1ccccc1 MGKWYRSLGCEEHX-DBICJICXSA-N 0.000 description 1
- GKWVPUHAFAYKSZ-UHFFFAOYSA-N NC1=CCCC=C1 Chemical compound NC1=CCCC=C1 GKWVPUHAFAYKSZ-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 241000207961 Sesamum Species 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-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
- 125000001931 aliphatic group Chemical group 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
- 150000001412 amines Chemical class 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 125000005104 aryl silyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- 125000004622 benzoxazinyl group Chemical group O1NC(=CC2=C1C=CC=C2)* 0.000 description 1
- 239000004305 biphenyl Substances 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
- IQUSEKZKDMXHOY-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c1nc(-c(cc2)ccc2-c2cc(cccc3)c3cc2)nc(-c2c3[s]c4ccccc4c3ccc2)n1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c1nc(-c(cc2)ccc2-c2cc(cccc3)c3cc2)nc(-c2c3[s]c4ccccc4c3ccc2)n1 IQUSEKZKDMXHOY-UHFFFAOYSA-N 0.000 description 1
- VEMDAMFBPQKZLL-UHFFFAOYSA-N c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2cc(cccc3)c3cc2)nc(-c2c(c3ccccc3[s]3)c3ccc2)n1 Chemical compound c(cc1)ccc1-c(cc1)ccc1-c1nc(-c2cc(cccc3)c3cc2)nc(-c2c(c3ccccc3[s]3)c3ccc2)n1 VEMDAMFBPQKZLL-UHFFFAOYSA-N 0.000 description 1
- FBQIZPFBLLDSFB-UHFFFAOYSA-N c(cc1)ccc1-c1cc(-c(cc2)ccc2-c2nc(-c3ccccc3)nc(-c(cc3)cc4c3c3ccccc3[o]4)n2)cc(-c2ccccc2)c1 Chemical compound c(cc1)ccc1-c1cc(-c(cc2)ccc2-c2nc(-c3ccccc3)nc(-c(cc3)cc4c3c3ccccc3[o]4)n2)cc(-c2ccccc2)c1 FBQIZPFBLLDSFB-UHFFFAOYSA-N 0.000 description 1
- MTIXQFZWEVKYRZ-UHFFFAOYSA-N c(cc1)ccc1-c1cc(-c(cc2)ccc2-c2nc(-c3ccccc3)nc(-c(cc3)cc4c3c3ccccc3[o]4)n2)ccc1 Chemical compound c(cc1)ccc1-c1cc(-c(cc2)ccc2-c2nc(-c3ccccc3)nc(-c(cc3)cc4c3c3ccccc3[o]4)n2)ccc1 MTIXQFZWEVKYRZ-UHFFFAOYSA-N 0.000 description 1
- YUPXRVKZUWIMQD-UHFFFAOYSA-N c(cc1)ccc1-c1cccc(-c2cc(-c3nc(-c4ccc(c(cccc5)c5[o]5)c5c4)nc(-c(cc4)cc5c4c4ccccc4[o]5)n3)ccc2)c1 Chemical compound c(cc1)ccc1-c1cccc(-c2cc(-c3nc(-c4ccc(c(cccc5)c5[o]5)c5c4)nc(-c(cc4)cc5c4c4ccccc4[o]5)n3)ccc2)c1 YUPXRVKZUWIMQD-UHFFFAOYSA-N 0.000 description 1
- RAOCWDRTTMIEFV-UHFFFAOYSA-N c(cc1)ccc1-c1cccc(-c2cc(-c3nc(-c4ccccc4)nc(-c(cc4)cc5c4c4ccccc4[o]5)n3)cc(-c3ccccc3)c2)c1 Chemical compound c(cc1)ccc1-c1cccc(-c2cc(-c3nc(-c4ccccc4)nc(-c(cc4)cc5c4c4ccccc4[o]5)n3)cc(-c3ccccc3)c2)c1 RAOCWDRTTMIEFV-UHFFFAOYSA-N 0.000 description 1
- NVXMXYUOCQSRRB-UHFFFAOYSA-N c(cc1)ccc1-c1nc(-c2c(c3ccccc3[o]3)c3ccc2)nc(-c(cc2)ccc2-c2cc(cccc3)c3cc2)n1 Chemical compound c(cc1)ccc1-c1nc(-c2c(c3ccccc3[o]3)c3ccc2)nc(-c(cc2)ccc2-c2cc(cccc3)c3cc2)n1 NVXMXYUOCQSRRB-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 125000002676 chrysenyl group Chemical group C1(=CC=CC=2C3=CC=C4C=CC=CC4=C3C=CC12)* 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([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
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- ZOCHARZZJNPSEU-UHFFFAOYSA-N diboron Chemical compound B#B ZOCHARZZJNPSEU-UHFFFAOYSA-N 0.000 description 1
- VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- DKHNGUNXLDCATP-UHFFFAOYSA-N dipyrazino[2,3-f:2',3'-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile Chemical compound C12=NC(C#N)=C(C#N)N=C2C2=NC(C#N)=C(C#N)N=C2C2=C1N=C(C#N)C(C#N)=N2 DKHNGUNXLDCATP-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical group 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
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 238000007747 plating Methods 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- WPYJKGWLDJECQD-UHFFFAOYSA-N quinoline-2-carbaldehyde Chemical group C1=CC=CC2=NC(C=O)=CC=C21 WPYJKGWLDJECQD-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000006836 terphenylene 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
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 125000004950 trifluoroalkyl group Chemical group 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
-
- 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
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- 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
Definitions
- composition for phosphorescent host, organic optoelectronic device and display device Composition for phosphorescent host, organic optoelectronic device and display device
- a composition for a phosphorescent host, an organic optoelectronic device, and a display device is provided.
- Organic optoelectronic diodes are devices that can switch electrical energy and light energy.
- Organic optoelectronic devices can be divided into two types according to the principle of operation.
- One is an optoelectronic device in which an exciton formed by light energy is separated into electrons and holes, and the electrons and holes are transferred to other electrodes, respectively, to generate electrical energy.
- It is a light emitting device that supplies and generates light energy from electrical energy.
- Examples of the organic optoelectronic device may be an organic photoelectric device, an organic light emitting device, an organic solar cell and an organic photo conductor drum.
- organic light emitting diodes are attracting much attention as demand for flat panel display devices increases.
- the organic light emitting device converts electrical energy into light by applying an electric current to the organic light emitting material.
- the organic light emitting device has a structure in which an organic layer is inserted between an anode and a cathode.
- the organic layer may include a light emitting layer and optionally an auxiliary layer, and the auxiliary insect may include, for example, a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, an electron injection layer, and the like, to increase the efficiency and stability of the organic light emitting device. It may comprise at least one layer selected from the hole blocking layer.
- the performance of the organic light emitting device is greatly influenced by the characteristics of the organic layer, and in particular, is affected by the organic material included in the organic layer.
- One embodiment provides a composition for a phosphorescent host that can implement high efficiency and long life organic optoelectronic devices.
- Another embodiment provides an organic optoelectronic device comprising the composition.
- Another embodiment provides a display device including the organic optoelectronic device.
- An organic optoelectronic device including a dopant is provided.
- X 1 is O or S
- Z 1 to Z 3 are each independently N or CR a ,
- At least two of Z 1 to Z 3 are N,
- L 1 to L 3 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group
- a 1 and A 2 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
- At least one of A 1 and A 2 is a substituted or unsubstituted C6 to C30 aryl group
- R a and R 1 to R 3 are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, Or a substituted or unsubstituted C6 to C20 aryl group
- Ar 2 is a substituted or unsubstituted C6 to C20 aryl group
- b and R 6 to R 12 are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C20 aryl group.
- a red phosphorescent host composition comprising a crab host represented by Formula 1 and a crab 2 host represented by a combination of Formulas 2 and 3 is provided.
- a display device including the organic optoelectronic device is provided.
- FIG. 1 and 2 are cross-sectional views illustrating an organic light emitting diode according to an embodiment. ⁇ Explanation of sign>
- substituted means that at least one hydrogen in a substituent or compound is a deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substitution or Unsubstituted C1 to C40 silyl group, C1 to C30 alkyl group, CI to CIO alkylsilyl group, C6 to C30 arylsilyl group, C3 to C30 cycloalkyl group, C3 to C30 heterocycloalkyl group, C6 to C30 aryl group, C2 to C30 heteroaryl group, C1 to C20 alkoxy group, C1 To C10 trifluoroalkyl group, cyano group, or a combination thereof.
- substituted means that at least one hydrogen of the substituent or compound is substituted with deuterium, cyano group, C1 to C10 alkyl group, C6 to C20 aryl group, or C2 to C20 heterocyclic group.
- the "substituted” means that at least one hydrogen is substituted with deuterium, cyano group, C1 to C4 alkyl group, C6 to C12 aryl group or C2 to C12 heterocyclic group.
- substituted means that at least one hydrogen of the substituent or compound is deuterium, cyano group, C1 to C5 alkyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group,
- substituted means that at least one hydrogen in the substituent or compound is deuterium, cyano group, methyl group, ethyl group, propaneyl group, butyl group, phenyl group, pam-biphenyl group, meta-bi Mean substituted by a phenyl group, dibenzofuranyl group or dibenzothiophenyl group.
- hetero means one to three hetero atoms selected from the group consisting of ⁇ , ⁇ , S, P, and Si in one functional group, and the remainder is carbon unless otherwise defined.
- an "alkyl group” is aliphatic
- the alkyl group may be a "saturated alkyl group" that does not contain any double or triple bonds.
- the alkyl group may be an alkyl group of C1 to C30. More specifically, the alkyl group may be a C1 to C20 alkyl group or a C1 to C10 alkyl group.
- a C1 to C4 alkyl group means that the alkyl chain contains 1 to 4 carbon atoms, and methyl, ethyl, propyl, iso-propyl, ⁇ -butyl, iso-butyl, sec -butyl and t-butyl Selected from the group consisting of:
- alkyl group examples include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, nuclear group, cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclonucleus It means a practical skill.
- an "aryl group” refers to a group of groups having one or more hydrocarbon aromatic moieties.
- All of the elements of the hydrocarbon aromatic moiety have a P-orbital, and include a form in which these P-orbitals form a conjugate, such as a phenyl group, a naphthyl group,
- hydrocarbon aromatic moieties are linked through sigma bonds, such as biphenyl groups, terphenyl groups, quarterphenyl groups, etc.
- Aryl group are monocyclic, polycyclic or fused ring polycyclic (i.e.
- heterocyclic group is a higher concept including a heteroaryl group, and instead of carbon (C) in a ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof, N, O, It means containing at least one hetero atom selected from the group consisting of S, P and Si.
- the heterocyclic group may include one or more heteroatoms for all or each ring.
- heteroaryl group means containing at least one hetero atom selected from the group consisting of N, O, S, P and Si in the aryl group.
- Two or more heteroaryl groups may be directly connected through a sigma bond, or when the heteroaryl group includes two or more rings, two or more rings may be fused to each other.
- each ring may include 1 to 3 heteroatoms.
- the heterocyclic group may include, for example, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and the like.
- a substituted or unsubstituted C6 to C30 aryl group and / or a substituted or unsubstituted C2 to C30 heterocyclic group a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthra A senyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, Substituted or unsubstituted biphenyl group, substituted or unsubstituted P-terphenyl group, substituted or unsubstituted m-terphenyl group, substituted or unsubstituted 0-terphenyl group, substituted or unsubstituted
- Chrysenyl group substituted or unsubstituted triphenylene group, substituted or unsubstituted perenyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted indenyl group, substituted or unsubstituted furanyl group, substituted or unsubstituted A substituted thiophenyl group, a substituted or unsubstituted pyrylyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, Substituted or unsubstituted thiazolyl group, substituted or unsubstituted oxadiazolyl group, substituted or unsubstituted
- Thiadiazolyl group substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted benzofuranyl group, substituted Or unsubstituted benzothiophenyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted indolyl group, substituted or unsubstituted quinolinal group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted A quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group,
- Acridinyl group substituted or unsubstituted phenazineyl group, substituted or unsubstituted phenthiazineyl group, substituted or unsubstituted phenoxazineyl group, substituted or unsubstituted carbazoleyl group, substituted or unsubstituted dibenzofuranyl group , Or a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof, but is not limited thereto.
- the hole characteristic refers to a characteristic capable of forming holes by donating electrons when an electric field is applied, and injecting holes formed at the anode into the light emitting layer having conductive properties along the HOMO level, and emitting layer. It refers to a property that facilitates the movement of the hole formed in the anode and movement in the light emitting layer.
- the electron characteristic refers to a characteristic in which electrons can be received when an electric field is applied, and has a conductivity characteristic along the LUMO level, injecting electrons formed at the cathode into the light emitting layer, moving electrons formed in the light emitting layer to the cathode, and It means a property that facilitates movement.
- an organic optoelectronic device according to an embodiment is described.
- the organic optoelectronic device may switch between electrical energy and light energy. It will not specifically limit, if it is an element, For example, an organic photoelectric element, an organic light emitting element, an organic solar cell, an organic photosensitive drum, etc. are mentioned.
- an organic light emitting diode 100 includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 positioned between the anode 120 and the cathode 1 10. It includes ⁇ .
- the anode 120 may be made of, for example, a conductor having a high hole function, for example, to facilitate hole injection, and may be made of, for example, a metal, a metal oxide, and / or a conductive polymer.
- the anode 120 is, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold or an alloy thereof; Zinc oxide, indium oxide, indium tin oxide (ITO),
- Metal oxides such as indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO and A1 or Sn0 2 and Sb; Conductive polymers such as poly (3-methylthiophene), poly (3,4- (ethylene- 1,2-dioxy) thiophene) (polyehtylenedioxythiophene: PEDT), polypyrrole and polyaniline, and the like. It is not limited.
- the cathode 110 may be made of a low work function conductor, for example, to facilitate electron injection, and may be made of metal, metal oxide and / or conductive polymer, for example.
- Cathode 110 is, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, sesame, barium, or an alloy thereof; Multi-layered materials such as LiF / Al, LiC3 ⁇ 4 / Al, LiF / Ca, LiF / Al, and BaF 2 / Ca, but are not limited thereto.
- the organic layer 105 includes an auxiliary layer including at least one of a hole injection layer, a hole transport layer, an electron injection layer, and an electron transport layer, and a light emitting layer 130.
- FIG. 2 is a cross-sectional view illustrating an organic light emitting device according to another embodiment.
- the organic light emitting diode 200 further includes a hole auxiliary layer 140 in addition to the light emitting layer 130.
- the hole auxiliary layer 140 may further increase hole injection and / or hole mobility between the anode 120 and the light emitting layer 130 and block electrons.
- the hole auxiliary layer 140 may be, for example, a hole transport layer, a hole injection layer, and / or an electron blocking layer, and may include at least one layer.
- the organic layer 105 of FIG. 1 or 2 may further include an electron injection layer, an electron transport layer, an electron transport auxiliary layer, a hole transport layer, a hole transport auxiliary layer, a hole injection layer, or a combination thereof. have.
- the organic light emitting diodes 100 and 200 may be formed by forming an anode or a cathode on a substrate, followed by a dry film method such as evaporation, sputtering, plasma plating, and ion plating; or spin coating or needle coating. After forming the organic layer by a wet film method such as dipping, flow coating, or the like, it may be prepared by forming a cathode or an anode thereon.
- the organic optoelectronic device includes an anode and a cathode facing each other, and an organic layer positioned between the anode and the cathode, wherein the organic layer is a hole injection layer, a hole transport layer, an electron injection layer, and an electron transport layer.
- X 1 is ⁇ or S
- ⁇ 1 to ⁇ 3 are each independently ⁇ or CR a and
- At least two of Z 1 to Z 3 are N,
- L 1 to L 3 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group
- a 1 and A 2 are each independently a substituted or unsubstituted C6 to C30 aryl group, and a ⁇ substituted or unsubstituted C2 to C30 heterocyclic group, At least one of A 1 and A 2 is a substituted or unsubstituted C6 to C30 aryl group, R a and R 1 to R 3 are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 internal C10 alkyl group, Or a substituted or unsubstituted C6 to C20 aryl group; In Chemical Formulas 2 and 3,
- Ar 2 is a substituted or unsubstituted C6 to C20 aryl group
- R b and R 6 to R 12 are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C20 aryl group.
- the organic optoelectronic device according to the present invention comprises a structure in which dibenzofuran (or dibenzothiophene) binds to a triazine or pyrimidine moiety as a first host, thereby expanding the LUMO and the planar expansion of the ET moiety. And an injection speed of electrons.
- the HOMO electron cloud is expanded in comparison with the structure having only the non-fused aryl, and has a structure favorable for hopping of the hole, resulting in high hole mobility and High glass transition temperature and thermal stability compared to the molecular weight can be ensured, the long life characteristics can be realized in the red region of the maximum emission wavelength of 550 nm to 750 nm.
- ⁇ 1 to ⁇ 3 may be all N.
- R 1 to R 3 may be each independently hydrogen or a phenyl group.
- a 1 and A 2 of Formula 1 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, A 1 and Any one of A 2 is a substituted or unsubstituted C 6 to C 30 aryl group.
- a 1 is a substituted or unsubstituted C6 to C30 aryl group
- a 2 is a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 hetero It may be a ring group.
- a 1 may be a substituted or unsubstituted C6 to C20 aryl group, wherein A 1 is, for example, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted group. It may be a substituted terphenyl group, a substituted or unsubstituted quarterphenyl group, or a substituted or unsubstituted naphthyl group, wherein Formula 1 may be represented by the following Formula 1_I.
- R 1 to R 3 are as defined above, R 4 and R 5 are defined in the foregoing R 1 To R 3 .
- a 1 of Formula 1 may be selected from the substituents listed in Group I below, for example.
- * is the point of attachment to L 2 .
- a 2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quarterphenyl group, a substituted or unsubstituted di Benzofuranyl group, substituted or unsubstituted
- the first host may be represented by any one of the following Chemical Formulas 1-1-1 to 1-1-3 according to the specific type of A 2 .
- Ar 1 of Formula 1-1-1 may be a substituted or unsubstituted C6 to C20 aryl group, specifically substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted naphthyl group , A substituted or unsubstituted terphenyl group, or a substituted or unsubstituted quarterphenyl group, wherein the additional substituent may be a deuterium, cyano group, phenyl group, or naphthyl group.
- R C and R D in Formula 1-1-3 may each independently be a substituted or unsubstituted C6 to C20 aryl group, more specifically a phenyl group, a biphenyl group, a naphthyl group or ter It may be a phenyl group.
- a 2 of Formula 1 may be selected from, for example, the substituents listed in the following group ⁇ .
- the Crab 1 host may be represented by Formula 1-1-1 or Formula 1-1-2, wherein R 4 and R 5 are each, for example,
- Ar 1 of Formula l-1-l is, for example, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted It may be a naphthyl group or a substituted or unsubstituted terphenyl group
- X 2 of Formula 1-1 -2 is 0 or S
- R c , R d and R e are each independently hydrogen, deuterium, cyano group or It may be a phenyl group.
- Chemical Formula 1-1 may be any one of the following Chemical Formula 1-IA, Chemical Formula 1-IB, Chemical Formula 1-1 C, and Chemical Formula 1-ID according to the specific substitution position of the dibenzofuranyl group (or dibenzothiophenyl group). Can be expressed.
- R 5 tear A 2 The definition of R 5 tear A 2 is as described above.
- Chemical Formula 1-1 may be represented by Chemical Formula 1-IB, and more specifically, Chemical Formula 1-IB may be represented by Chemical Formulas 1-I B-1 to Chemical Formula 1-1 It can be represented by any one of B-3.
- the formula 1-1 B-1 or the formula 1-IB-2 is preferred.
- R c and R d of Chemical Formula 1-IB-3 of the present invention may be independently a substituted or unsubstituted C6 to C20 aryl group, more specifically a phenyl group, It may be a biphenyl group, a naphthyl group, or a terphenyl group.
- L 1 to L 3 are each independently a single bond or a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, or It may be a substituted or unsubstituted naphthyleneylene group, for example, it may be selected from the linking groups listed in the group m below.
- L 1 to L 3 may be each independently a single bond or an unsubstituted phenylene group. More specifically, L 1 may be a single bond or an unsubstituted phenylene group, but a single bond is more preferable.
- Formula 1-1 -1 may be represented by the following Formula 1-1 -la or Formula 1-I -lb,
- Formula 1-I-2 may be represented by the following Formula 1-I-2a
- Formula 1-I -3 is represented by Formula 1-I-3a, Formula 1-I-3b, Formula 1-I-3c, Formula 1-1-3d, Formula 1-1-3e, and Formula 1-1 It can be represented by any one of 3f.
- R 1 to R 3 of Formula 1-I-la, Formula 1-I-lb, Formula 1-I-2a, and Formulas 1-I-3a to l-I-3f are each independently hydrogen, Deuterium, phenyl group, or biphenyl group
- R 4 and R 5 may each independently be hydrogen, deuterium, phenyl group, biphenyl group, or terphenyl group, more preferably R 1 to R 3 are all hydrogen
- R 4 and R 5 may be each independently hydrogen, a phenyl group, or a biphenyl group.
- It may be a pyrimidinyl group or a triazinyl group, and more preferably, it may be a triazinyl group.
- the first host is for example the formula It may be represented by 1-1-1 or formula 1-1-2, and more preferably may be represented by the formula 1-1 -la, the formula 1-1 I.lb and the formula 1-1 I-2a.
- the crab 1 host may be, for example, represented by Chemical Formula 1-IB, and more preferably, may be represented by Chemical Formula 1-1 B-1 or Chemical Formula 1-IB-2.
- the first host may be selected from, for example, the compounds listed in Group 1 below, but is not limited thereto.
- the second host may be represented by any one of the following Chemical Formula 2A, Chemical Formula 2B, Chemical Formula 2C, Chemical Formula 2D, Chemical Formula 2E, and Chemical Formula 2F, depending on the fusion position of Chemical Formula 2 and Chemical Formula 3.
- Ar 2 may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted terphenyl group.
- the second host may be represented by the formula (2C), it may be represented by, for example, the formula 2C-a or 2C-b according to the substitution point of the naphthyl group.
- Ar 2 , L al , L a2 , Y 1 , Y 2 , R bl , R b2, and R 6 to R ′ 2 are the same as defined above.
- the crab 1 host is represented by Chemical Formula 1-
- the C 1 host may be represented by Chemical Formula 1-1 B-1 or Chemical Formula 1-I B-2.
- R bl and R b2 of Formula 2C-a, and R 6 to R 12 are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted phenyl group, substituted or unsubstituted
- L al and L a2 , and Y 1 and Y 2 are each independently a single bond, a substituted or unsubstituted para-phenylene group, a substituted or unsubstituted meta-phenylene group, or a substituted or unsubstituted biphenylene. It may be a flag.
- R 6 to R 9 may be each independently hydrogen, deuterium, cyano group or phenyl group, all may be hydrogen.
- R 10 to R 12 may be each independently hydrogen, deuterium, cyano group, or phenyl group, more specifically may be hydrogen or phenyl group.
- Ar 2 may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group or a substituted or unsubstituted terphenyl group.
- Substituents to be substituted may be deuterium, cyano group, phenyl group or naphthyl group.
- the crab 2 host may be selected from, for example, the compounds listed in Group 2, but is not limited thereto.
- the first host and the second host may be applied in the form of a composition.
- the present invention provides a red phosphorescent host composition
- a red phosphorescent host composition comprising the first host represented by the following Chemical Formula 1, and the second host represented by the combination of the following Chemical Formula 2 and Chemical Formula 3.
- red means a range in which the maximum emission wavelength of the phosphorescent dopant is 550 nm to 750 nm. That is, the maximum emission wavelength of the dopant of the light emitting device to which the composition of the present invention is applied means a long wavelength region beyond the green region.
- the organic optoelectronic device of the present invention includes a phosphorescent dopant having a maximum emission wavelength of 550 nm to 750 nm. That is, it includes a phosphorescent dopant whose maximum emission wavelength is out of the green region.
- the maximum light emission wavelength which is a wavelength representing a redish region, may be 560 nm to 750 nm, and may be 570 nm to 720 nm, 580 nm to 700 nm, 590 nm to 700 nm, 600 nm to 700 nm, and the like. .
- the phosphorescent dopant having a maximum emission wavelength of 550 nm to 750 nm may be an iridium (Ir) complex or a platinum () complex, and the platinum (Pt) complex may be represented by, for example, Chemical Formula 4-1.
- the iridium (Ir) complex may be represented by, for example, the following Chemical Formula 4-2.
- X ⁇ , X s , X and ⁇ ⁇ are each an element which forms an unsaturated ring with 1A, 1B, 1C and ID, and are each independently C or N,
- 1A, IB, 1C, and ID are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
- L s , L c , L D , Q A , Q B , Q c and Q D are each independently a single bond, O, S, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted A C2 to C30 alkenylene group, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group,
- R A , R B , R c and 1 ⁇ are each independently hydrogen, deuterium, cyano group, halogen group, silane group, phosphine group, amine group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30
- R A , R B , R c and are each independently present or adjacent groups are connected to each other to form a ring
- n is one of integers from 0 to 5
- a, b, c and d are each independently one of an integer of 0-3.
- 2A, 2B and 2C are each independently a substituted or unsubstituted benzene ring
- At least one of 2A, 2B and 2C forms a fused ring with an adjacent complex
- R E , R F , R G , R H , R 7 , R J and I ⁇ are each independently hydrogen, deuterium, cyano group, Halogen, silane, phosphine, amine, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30
- R E , R F , R G , R H , R 7 , R y and are each independently or adjacent groups are connected to each other to form a ring,
- n is one of the integers 1-3.
- the platinum (Pt) complex may be represented by the following Formula 4 or Chemical Formula la _ 4-lb.
- 1A, 1B, 1C and 1D may be each independently a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C20 heterocyclic group, and more Specifically, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted Pyridinyl groups, substituted or unsubstituted benzimidazolyl groups, substituted or unsubstituted
- Benzothiazole group substituted or unsubstituted benzoxazole group, substituted or unsubstituted pyryl group, substituted or unsubstituted pyrazolyl group, substituted or unsubstituted imidazolyl group, substituted or unsubstituted oxazolyl group And may be selected, for example, from the groups listed in Group IV below, and the groups listed in Group IV below may be further substituted.
- X is an element forming an unsaturated ring with 1A, 1B, 1C and 1D and each independently is C or N. Additional substituents are deuterium, cyano, halogen, C1 To CIO alkyl group, or C1 to C10 fluoroalkyl group.
- the ⁇ , ⁇ , 1C and 1D are substituted or unsubstituted phenyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted benzothiazole group, substituted Or an unsubstituted pyryl group, a substituted or unsubstituted pyrazolyl group.
- specific embodiments of the present invention also include a structure in which adjacent groups of I ⁇ , R S , R C and R ° are fused to form a ring.
- R S , R C and R ° are fused to form a ring.
- the iridium (Ir) complex may be represented by the following formula (4-2a), or formula (4-2b).
- R £ , R F , R G , R H , R r , R J , R K , R L , R M and R w are hydrogen, deuterium, cyano group, halogen group, It may be a C1 to C10 alkyl group, or a C1 to C10 fluoroalkyl group.
- specific embodiments of the present invention also include a structure in which adjacent groups of R £ , R, R G , and R "are fused to form a ring.
- a form such as Compound 4-12 of Group 3 may be exemplified. have.
- the phosphorescent dopant may be selected from, for example, the compounds listed in Group 3, but is not limited thereto.
- the first host is represented by the 1-1 B-1 or Formula 1-1 I-2
- the second host is represented by the formula 2C-a
- the dopant may be represented by Chemical Formula 4-2a.
- the first host and the crab 2 host may be included in the increase ratio of 1: 9 to 5: 5, 2: 8 to 5: 5 3: 7 to 5: 5, wherein the phosphorescent dopant is 1 and to the host with respect to 100 parts by weight of the composition 0 /. of the second host may be included as 0.1 to 50 wt. 0/0.
- the crab first host and the second host is 3: 7 to 5: can be included in a weight ratio of from 5, wherein the phosphorescent dopyeon teuneun for the first host and a composition of 100 parts by weight 0/0 of the second host from 0.1 to 10 It may be included in weight percent.
- the first host and the second host may be included in a weight ratio of 3: 7 or 5: 5, the phosphorescent dopant is 0.5 to 10% by weight based on 100% by weight of the composition of the first host and the crab 2 host It may include 0/0.
- the red phosphorescent host composition according to another embodiment may include a first host represented by Chemical Formula 1 and a low] 2 host represented by a combination of Chemical Formulas 2 and 3.
- the first host may be represented by Chemical Formula 1-1
- the second host may be represented by Chemical Formula 2C.
- the crab 1 host may be represented by Formula 1-1 B-1 or Formula 1-I B-2, wherein Ar 1 of Formula 1-I B- 1 is It may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted quarterphenyl group.
- Ar 1 of Formula 1-I B- 1 is It may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted quarterphenyl group.
- the definition of other substituents is as described above.
- the organic light emitting diode described above may be applied to an organic light emitting display device. [Form for implementation of invention]
- Bispinacola was also added with 1.2 equivalents of diborone and 2 equivalents of potassium acetate and heated to reflux for 18 hours under a nitrogen atmosphere.
- the reaction solution is allowed to stand and dipped in 1 L of water to obtain a solid.
- the obtained solid is dissolved in boiling toluene, treated with activated carbon, filtered through silica gel, and the filtrate is concentrated. After stirring the concentrated solid with a small amount of nucleic acid, the solid was filtered
- Indium tin oxide was thin film-coated glass substrate with a thickness of 1500 A and washed with distilled water ultrasonically. After distilled water wash, isopropyl alcohol, acetone, methanol Ultrasonic cleaning with a solvent, and the like was dried and then transferred to a plasma cleaner, and then the substrate was cleaned for 10 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
- Compound A was vacuum deposited on the ITO substrate to form a hole injection layer having a thickness of 700 A using the prepared ⁇ transparent electrode as an anode, and then compound C was deposited to a thickness of 50 A on the injection layer. Deposition to a thickness to form a hole transport layer.
- Compound C-1 was deposited to a thickness of 400 A on the hole transport layer to form a hole transport auxiliary layer.
- Compound B-24 and Compound HC-28 were simultaneously used as a host on the hole transport auxiliary layer, and the light emitting layer having a thickness of 400A was formed by vacuum evaporation with 2 wt% of [Ir (piq) 2 acac].
- compound B-24 and compound HC-28 were used in a 3: 7 weight ratio.
- the compound D and Liq are simultaneously vacuum deposited on the light emitting layer at a ratio of 1: 1 to form an electron transport layer having a thickness of 300 A, and the Liq l5A and A1 1200A are sequentially vacuum deposited on the electron transport layer to form a cathode.
- the device was produced.
- the organic light emitting device has a structure having five organic thin film layers, specifically as follows.
- Compound B 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN),
- Example 1 to 9 Performed using polar Optronics lifetime measuring system for the manufacture of organic light emitting device in Example 1 to 9 and Reference Examples 1 to 3, the initial luminance of the device of (cd / m 2) the brightness of the light emission and time in 9000cd / m 2 The decrease in luminance was measured by the T97 life time when the luminance was reduced to 97% of the initial luminance.
- the lifetime of Reference Example 1 was expressed as a relative ratio with 100%.
- the organic light emitting device according to Examples 1 to 9 it can be seen that the life characteristics are significantly improved compared to the organic light emitting device according to Reference Examples 1 to 3.
- the present invention is not limited to the above embodiments, but may be manufactured in various forms, and a person of ordinary skill in the art to which the present invention pertains does not change the technical spirit or essential features of the present invention. It will be appreciated that the present invention may be practiced as. Therefore, it should be understood that the embodiments described above are exemplary in all respects and not restrictive.
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Abstract
Provided are a phosphorescent host composition comprising a first host represented by chemical formula 1, and a second host represented by a combination of chemical formulas 2 and 3; an organic optoelectronic diode comprising an anode and a cathode facing each other, and an organic layer disposed between the anode and the cathode, wherein the organic layer includes an auxiliary layer inclusive of at least one of a hole injection layer, a hole transport layer, an electron injection layer, and an electron transport layer, and a light-emitting layer in which a phosphorescent dopant with a maximum emission wavelength of 550 nm to 750 nm is included, together with the composition; and a display device comprising the diode. Detailed specifications for chemical formulas 1 to 3 is as defined in the description.
Description
【명세서】 【Specification】
【발명의 명칭】 [Name of invention]
인광 호스트용 조성물, 유기 광전자 소자 및 표시 장치 Composition for phosphorescent host, organic optoelectronic device and display device
【기술분야】 Technical Field
인광 호스트용 조성물, 유기 광전자 소자 및 표시 장치에 관한 것이다. A composition for a phosphorescent host, an organic optoelectronic device, and a display device.
【배경기술】 Background Art
유기 광전자 소자 (organic optoelectronic diode)는 전기 에너지와 광 에너지를 상호 전환할 수 있는 소자이다. Organic optoelectronic diodes are devices that can switch electrical energy and light energy.
유기 광전자 소자는 동작 원리에 따라 크게 두 가지로 나눌 수 있다. 하나는 광 에너지에 의해 형성된 액시톤 (exciton)이 전자와 정공으로 분리되고 상기 전자와 정공이 각각 다른 전극으로 전달도]면서 전기 에너지를 발생하는 광전 소자이고， 다른 하나는 전극에 전압 또는 전류를 공급하여 전기 에너지로부터 광 에너지를 발생하는 발광 소자이다. Organic optoelectronic devices can be divided into two types according to the principle of operation. One is an optoelectronic device in which an exciton formed by light energy is separated into electrons and holes, and the electrons and holes are transferred to other electrodes, respectively, to generate electrical energy. It is a light emitting device that supplies and generates light energy from electrical energy.
유기 광전자 소자의 예로는 유기 광전 소자, 유기 발광 소자, 유기 태양 전지 및 유기 감광체 드럼 (organic photo conductor drum) 등을 들 수 있다. Examples of the organic optoelectronic device may be an organic photoelectric device, an organic light emitting device, an organic solar cell and an organic photo conductor drum.
이 중， 유기 발광 소자 (organic light emitting diode, OLED)는 근택 평판 표시 장치 (flat panel display device)의 수요 증가에 따라 크게 주목받고 있다. 상기 유기 발광 소자는 유기 발광 재료에 전류를 가하여 전기 에너지를 빛으로 전환시키는 소자로서， 통상 양극 (anode)과 음극 (cathode) 사이에 유기 층이 삽입된 구조로 이루어져 있다. 여기서 유기 층은 발광층과 선택적으로 보조층을 포함할 수 있으며 상기 보조충은 예컨대 유기발광소자의 효율과 안정성을 높이기 위한 정공 주입 층, 정공 수송 층, 전자 차단 층， 전자 수송 층, 전자 주입 층 및 정공 차단 층에서 선택된 적어도 1층을 포함할 수 있다. Among these, organic light emitting diodes (OLEDs) are attracting much attention as demand for flat panel display devices increases. The organic light emitting device converts electrical energy into light by applying an electric current to the organic light emitting material. The organic light emitting device has a structure in which an organic layer is inserted between an anode and a cathode. The organic layer may include a light emitting layer and optionally an auxiliary layer, and the auxiliary insect may include, for example, a hole injection layer, a hole transport layer, an electron blocking layer, an electron transport layer, an electron injection layer, and the like, to increase the efficiency and stability of the organic light emitting device. It may comprise at least one layer selected from the hole blocking layer.
유기 발광 소자의 성능은 상기 유기 층의 특성에 의해 영향을 많이 받으며, 그 중에서도 상기 유기 층에 포함된 유기 재료에 의해 영향을 많이 받는다. The performance of the organic light emitting device is greatly influenced by the characteristics of the organic layer, and in particular, is affected by the organic material included in the organic layer.
특히 상기 유기 발광 소자가 대형 평판 표시 장치에 적용되기 위해서는 정공 및 전자의 이동성을 높이는 동시에 전기화학적 안정성을 높일 수 있는 유기 재료의 개발이 필요하다, In particular, in order for the organic light emitting diode to be applied to a large flat panel display, it is necessary to develop an organic material that can increase the mobility of holes and electrons and at the same time increase the electrochemical stability.
【발명의 상세한 설명】 [Detailed Description of the Invention]
【기술적 과제】
일 구현예는 고효율 및 장수명 유기 광전자 소자를 구현할 수 있는 인광 호스트용 조성물을 제공한다. [Technical problem] One embodiment provides a composition for a phosphorescent host that can implement high efficiency and long life organic optoelectronic devices.
다른 구현예는 상기 조성물을 포함하는 유기 광전자 소자를 제공한다. Another embodiment provides an organic optoelectronic device comprising the composition.
또 다른 구현예는 상기 유기 광전자 소자를 포함하는 표시 장치를 제공한다. 【기술적 해결방법] Another embodiment provides a display device including the organic optoelectronic device. Technical Solution
일 구현예에 따르면， 서로 마주하는 양극과 음극, 그리고 상기 양극과 상기 음극 사이에 위치하는 유기층을 포함하고, 상기 유기층은 정공 주입층, 정공 수 층， 전자주입층 및 전자 수송층 중 적어도 하나를 포함하는 보조층, 및 발광층을 포함하며, 상기 발광층은 하기 화학식 1로 표현되는 게 1 호스트, 하기 화학식 2 및 화학식 3의 조합으로 표현되는 제 2 호스트, 및 최대 발광 파장이 550 nm 내지 750 nm인 인광 도펀트를 포함하는 유기 광전자 소자를 제공한다. According to one embodiment, an anode and a cathode facing each other, and an organic layer positioned between the anode and the cathode, the organic layer comprises at least one of a hole injection layer, a hole number layer, an electron injection layer and an electron transport layer And an auxiliary layer, and a light emitting layer, wherein the light emitting layer includes one host represented by the following Chemical Formula 1, a second host represented by a combination of the following Chemical Formulas 2 and 3, and a maximum emission wavelength of 550 nm to 750 nm. An organic optoelectronic device including a dopant is provided.
화학식 1] [화학식 2] [화학식 3] Formula 1] [Formula 2 ] [Formula 3 ]
상기 화학식 1에서 In Chemical Formula 1
X1는 O 또는 S이고, X 1 is O or S,
Z1 내지 Z3은 각각 독립적으로 N 또는 CRa이고, Z 1 to Z 3 are each independently N or CR a ,
Z1 내지 Z3 중 적어도 둘은 N이고, At least two of Z 1 to Z 3 are N,
L1 내지 L3은 각각 독립적으로 단일결합, 또는 치환 또는 비치환된 C6 내지 C20 아릴렌기이고, L 1 to L 3 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,
A1 및 A2는 각각 독립적으로 치환 또는 비치환된 C6 내지 C30 아릴기， 또는 치환 또는 비치환된 C2 내지 C30 헤테로고리기이고, A 1 and A 2 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
A1 및 A2 중 적어도 하나는 치환 또는 비치환된 C6 내지 C30 아릴기이고, Ra 및 R1 내지 R3은 각각 독립적으로 수소, 중수소, 시아노기, 치환 또는 비치환된 C1 내지 C10 알킬기, 또는 치환 또는 비치환된 C6 내지 C20 아릴기이며; 상기 화학식 2 및 3에서,
Ar2는 치환 또는 비치환된 C6 내지 C20 아릴기이고, At least one of A 1 and A 2 is a substituted or unsubstituted C6 to C30 aryl group, R a and R 1 to R 3 are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, Or a substituted or unsubstituted C6 to C20 aryl group; In Chemical Formulas 2 and 3, Ar 2 is a substituted or unsubstituted C6 to C20 aryl group,
화학식 2의 인접한 2개의 *은 화학식 3과 연결되고, Two adjacent * of Formula 2 are linked to Formula 3,
화학식 3과 연결되지 않은 화학식 2의 *은 각각 독립적으로 C-La-Rb이고， ΙΛ Υ1 및 Y2는 각각 독립적으로 단일결합, 또는 치환 또는 비치환된 C6 내 C20 아릴렌기이고,* Of Formula 2, which is not linked to Formula 3, is each independently CL a -R b , and ΙΛ Υ 1 and Y 2 are each independently a single bond or a substituted or unsubstituted C20 arylene group in C6,
b 및 R6 내지 R12는 각각 독립적으로 수소, 중수소, 시아노기, 치환 또는 비치환된 C1 내지 C10 알킬기, 또는 치환 또는 비치환된 C6 내지 C20 아릴기이다. 다른 구현예에 따르면, 상기 화학식 1로 표현되는 게 1 호스트， 그리고 상기 화학식 2 및 화학식 3의 조합으로 표현되는 게 2 호스트를 포함하는 적색 인광 호스트용 조성물을 제공한다. b and R 6 to R 12 are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C20 aryl group. According to another embodiment, a red phosphorescent host composition comprising a crab host represented by Formula 1 and a crab 2 host represented by a combination of Formulas 2 and 3 is provided.
또 다른 구현예에 따르면, 상기 유기 광전자 소자를 포함하는 표시 장치를 제공한다. According to another embodiment, a display device including the organic optoelectronic device is provided.
【발명의 효과】 【Effects of the Invention】
고효율 장수명 유기 광전자 소자를 구현할 수 있다. High efficiency long life organic optoelectronic devices can be implemented.
【도면의 간단한 설명】 [Brief Description of Drawings]
도 1 및 도 2는 일 구현예에 따른 유기 발광 소자를 도시한 단면도이다. <부호의 설명〉 1 and 2 are cross-sectional views illustrating an organic light emitting diode according to an embodiment. <Explanation of sign>
100, 200: 유기 발광 소자 100 and 200: organic light emitting element
105: 유기층 105: organic layer
110: 음극 110: cathode
120: 양극 120: anode
130: 발광층 130: light emitting layer
140: 정공 보조층 140: hole auxiliary layer
【발명의 실시를 위한 최선의 형태】 [Best form for implementation of the invention]
이하, 본 발명의 구현예를 상세히 설명하기로 한다. 다만, 이는 예시로서 제시되는 것으로, 이에 의해 본 발명이 제한되지는 않으며 본 발명은 후술할 청구범위의 범주에 의히! 정의될 뿐이다. Hereinafter, embodiments of the present invention will be described in detail. However, this is presented as an example, by which the present invention is not limited and the present invention is defined by the scope of the claims to be described later! It is just defined.
본 명세서에서 "치환"이란 별도의 정의가 없는 한, 치환기 또는 화합물 중의 적어도 하나의 수소가 중수소， 할로겐기, 히드록실기, 아미노기, 치환 또는 비치환된 C1 내지 C30 아민기, 니트로기, 치환 또는 비치환된 C1 내지 C40 실릴기， C1 내지
C30 알킬기, CI 내지 CIO 알킬실릴기, C6 내지 C30 아릴실릴기, C3 내지 C30 시클로알킬기, C3 내지 C30 헤테로시클로알킬기， C6 내지 C30 아릴기, C2 내지 C30 헤테로아릴기， C1 내지 C20 알콕시기， C1 내지 C10 트리플루오로알킬기, 시아노기, 또는 이들의 조합으로 치환된 것을 의미한다. As used herein, unless otherwise defined, "substituted" means that at least one hydrogen in a substituent or compound is a deuterium, a halogen group, a hydroxyl group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, a substitution or Unsubstituted C1 to C40 silyl group, C1 to C30 alkyl group, CI to CIO alkylsilyl group, C6 to C30 arylsilyl group, C3 to C30 cycloalkyl group, C3 to C30 heterocycloalkyl group, C6 to C30 aryl group, C2 to C30 heteroaryl group, C1 to C20 alkoxy group, C1 To C10 trifluoroalkyl group, cyano group, or a combination thereof.
본 발명의 일 예에서, "치환"은 치환기 또는 화합물 중의 적어도 하나의 수소가 중수소， 시아노기, C1 내지 C10 알킬기， C6 내지 C20 아릴기, 또는 C2 내지 C20 헤테로고리기로 치환된 것을 의미한다. 또한， 본 발명의 구체적인 일 예에서, 상기 "치환"이란, 적어도 하나의 수소가 중수소, 시아노기, C1 내지 C4 알킬기, C6 내지 C12 아릴기 또는 C2 내지 C12 헤테로고리기로 치환된 것을 의미한다. 더욱 구체적으로 "치환 "은 치환기 또는 화합물 중의 적어도 하나의 수소가 중수소, 시아노기, C1 내지 C5 알킬기， 페닐기, 바이페닐기, 터페닐기, 나프틸기， In one embodiment of the present invention, "substituted" means that at least one hydrogen of the substituent or compound is substituted with deuterium, cyano group, C1 to C10 alkyl group, C6 to C20 aryl group, or C2 to C20 heterocyclic group. In addition, in a specific example of the present invention, the "substituted" means that at least one hydrogen is substituted with deuterium, cyano group, C1 to C4 alkyl group, C6 to C12 aryl group or C2 to C12 heterocyclic group. More specifically, "substituted" means that at least one hydrogen of the substituent or compound is deuterium, cyano group, C1 to C5 alkyl group, phenyl group, biphenyl group, terphenyl group, naphthyl group,
플루오레닐기， 벤조퓨란일기, 벤조티오펜일기， 디벤조퓨란일기, 디벤조티오펜일기 또는 카바졸일기로 치환된 것을 의미한다. 또한， 본 발명의 가장 구체적인 일 예에서，"치환"은 치환기 또는 화합물 중의 적에도 하나의 수소가 중수소， 시아노기, 메틸기, 에틸기, 프로판일기, 부틸기, 페닐기， pam-바이페닐기, meta-바이페닐기， 디벤조퓨란일기 또는 디벤조티오펜일기로 치환된 것을 의미한다. Mean substituted by a fluorenyl group, benzofuranyl group, benzothiophenyl group, dibenzofuranyl group, dibenzothiophenyl group or carbazolyl group. In addition, in the most specific example of the present invention, "substituted" means that at least one hydrogen in the substituent or compound is deuterium, cyano group, methyl group, ethyl group, propaneyl group, butyl group, phenyl group, pam-biphenyl group, meta-bi Mean substituted by a phenyl group, dibenzofuranyl group or dibenzothiophenyl group.
본 명세서에서 "헤테로"란 별도의 정의가 없는 한， 하나의 작용기 내에 Ν, Ο, S, P 및 Si로 이루어진 군에서 선택되는 헤테로 원자를 1 내지 3개 함유하고, 나머지는 탄소인 것을 의미한다. As used herein, "hetero" means one to three hetero atoms selected from the group consisting of Ν, Ο, S, P, and Si in one functional group, and the remainder is carbon unless otherwise defined. .
본 명세서에서 "알킬 (alkyl)기"이란 별도의 정의가 없는 한, 지방족 As used herein, unless otherwise defined, an "alkyl group" is aliphatic
탄화수소기를 의미한다. 알킬기는 어떠한 이중결합이나 삼중결합을 포함하고 있지 않은 "포화 알킬 (saturated alkyl)기 "일 수 있다. It means a hydrocarbon group. The alkyl group may be a "saturated alkyl group" that does not contain any double or triple bonds.
상기 알킬기는 C1 내지 C30인 알킬기일 수 있다. 보다 구체적으로 알킬기는 C1 내지 C20 알킬기 또는 C1 내지 C10 알킬기일 수도 있다. 예를 들어， C1 내지 C4 알킬기는 알킬쇄에 1 내지 4 개의 탄소원자가 포함되는 것을 의미하며, 메틸, 에틸, 프로필， 이소-프로필 , η-부틸, 이소-부틸, sec-부틸 및 t-부틸로 이루어진 군에서 선택됨을 나타낸다. The alkyl group may be an alkyl group of C1 to C30. More specifically, the alkyl group may be a C1 to C20 alkyl group or a C1 to C10 alkyl group. For example, a C1 to C4 alkyl group means that the alkyl chain contains 1 to 4 carbon atoms, and methyl, ethyl, propyl, iso-propyl, η-butyl, iso-butyl, sec -butyl and t-butyl Selected from the group consisting of:
상기 알킬기는 구체적인 예를 들어 메틸기， 에틸기， 프로필기， 이소프로필기, 부틸기, 이소부틸기, t-부틸기, 펜틸기， 핵실기， 시클로프로필기, 시클로부틸기, 시클로펜틸기， 시클로핵실기 등을 의미한다.
본 명세서에서 "아릴 (aryl)기 "는 탄화수소 방향족 모이어티를 하나 이상 갖는 그룹을 총괄하는 개념으로서, Specific examples of the alkyl group include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, nuclear group, cyclopropyl group, cyclobutyl group, cyclopentyl group and cyclonucleus It means a practical skill. As used herein, an "aryl group" refers to a group of groups having one or more hydrocarbon aromatic moieties.
탄화수소 방향족 모이어티의 모든 원소가 P-오비탈을 가지면서， 이들 P- 오비탈이 공액 (conjugation)을 형성하고 있는 형태， 예컨대 페닐기, 나프틸기 등을 포함하고, All of the elements of the hydrocarbon aromatic moiety have a P-orbital, and include a form in which these P-orbitals form a conjugate, such as a phenyl group, a naphthyl group,
2 이상의 탄화수소 방향족 모이어티들이 시그마 결합을 통하여 연결된 형태, 예컨대 바이페닐기， 터페닐기， 쿼터페닐기 등을 포함하며， Two or more hydrocarbon aromatic moieties are linked through sigma bonds, such as biphenyl groups, terphenyl groups, quarterphenyl groups, etc.
2 이상의 탄화수소 방향족 모이어티들이 직접 또는 간접적으로 융합된 비방향족 융합 고리도 포함할 수 있다. 예컨대, 플루오레닐기 등을 들 수 있다. 아릴기는 모노시클릭, 폴리시클릭 또는 융합 고리 폴리시클릭 (즉, It may also comprise a non-aromatic fused ring in which two or more hydrocarbon aromatic moieties are fused directly or indirectly. For example, a fluorenyl group may be mentioned. Aryl groups are monocyclic, polycyclic or fused ring polycyclic (i.e.
탄소원자들의 인접한 쌍들을 나눠 가지는 고리) 작용기를 포함한다ᅳ Contains a ring) functional group which shares adjacent pairs of carbon atoms.
본 명세서에서 "해테로고리기 (heterocyclic group)"는 헤테로아릴기를 포함하는 상위 개념으로서, 아릴기, 시클로알킬기, 이들의 융합고리 또는 이들의 조합과 같은 고리 화합물 내에 탄소 (C) 대신 Ν, Ο, S, P 및 Si로 이루어진 군에서 선택되는 헤테로 원자를 적어도 한 개를 함유하는 것을 의미한다. 상기 헤테로고리기가 융합고리인 경우, 상기 헤테로고리기 전체 또는 각각의 고리마다 헤테로 원자를 한 개 이상 포함할 수 있다. As used herein, the term "heterocyclic group" is a higher concept including a heteroaryl group, and instead of carbon (C) in a ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof, or a combination thereof, N, O, It means containing at least one hetero atom selected from the group consisting of S, P and Si. In the case where the heterocyclic group is a fused ring, the heterocyclic group may include one or more heteroatoms for all or each ring.
일 예로 "헤테로아릴 (heteroaryl)기 "는 아릴기 내에 N, O, S, P 및 Si로 이루어진 군에서 선택되는 헤테로 원자를 적어도 한 개를 함유하는 것을 의미한다. 2 이상의 헤테로아릴기는 시그마 결합을 통하여 직접 연결되거나， 상기 헤테로아릴기가 2 이상의 고리를 포함할 경우, 2 이상의 고리들은 서로 융합될 수 있다. 상기 헤테로아릴기가 융합고리인 경우， 각각의 고리마다 상기 헤테로 원자를 1 내지 3개 포함할 수 있다. For example, "heteroaryl group" means containing at least one hetero atom selected from the group consisting of N, O, S, P and Si in the aryl group. Two or more heteroaryl groups may be directly connected through a sigma bond, or when the heteroaryl group includes two or more rings, two or more rings may be fused to each other. When the heteroaryl group is a fused ring, each ring may include 1 to 3 heteroatoms.
상기 헤테로고리기는 구체적인 예를 들어, 피리디닐기, 피리미디닐기, 피라지닐기, 피리다지닐기， 트리아지닐기, 퀴놀리닐기, 이소퀴놀리닐기 등을 포함할 수 있다. The heterocyclic group may include, for example, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, and the like.
보다 구체적으로， 치환 또는 비치환된 C6 내지 C30 아릴기 및 /또는 치환 또는 비치환된 C2 내지 C30 헤테로고리기는， 치환 또는 비치환된 페닐기， 치환 또는 비치환된 나프틸기， 치환 또는 비치환된 안트라세닐기, 치환 또는 비치환된 페난트레닐기， 치환 또는 비치환된 나프타세닐기， 치환 또는 비치환된 피레닐기,
치환 또는 비치환된 바이페닐기， 치환 또는 비치환된 P-터페닐기, 치환 또는 비치환된 m-터페닐기， 치환 또는 비치환된 0-터페닐기， 치환 또는 비치환된 More specifically, a substituted or unsubstituted C6 to C30 aryl group and / or a substituted or unsubstituted C2 to C30 heterocyclic group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthra A senyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, Substituted or unsubstituted biphenyl group, substituted or unsubstituted P-terphenyl group, substituted or unsubstituted m-terphenyl group, substituted or unsubstituted 0-terphenyl group, substituted or unsubstituted
크리세닐기, 치환 또는 비치환된 트리페닐렌기, 치환 또는 비치환된 페릴레닐기， 치환 또는 비치환된 플루오레닐기, 치환 또는 비치환된 인데닐기, 치환 또는 비치환된 퓨라닐기, 치환 또는 비치환된 티오페닐기, 치환 또는 비치환된 피를릴기, 치환 또는 비치환된 피라졸릴기, 치환 또는 비치환된 이미다졸일기, 치환 또는 비치환된 트리아졸일기, 치환 또는 비치환된 옥사졸일기， 치환 또는 비치환된 티아졸일기, 치환 또는 비치환된 옥사디아졸일기, 치환 또는 비치환된 Chrysenyl group, substituted or unsubstituted triphenylene group, substituted or unsubstituted perenyl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted indenyl group, substituted or unsubstituted furanyl group, substituted or unsubstituted A substituted thiophenyl group, a substituted or unsubstituted pyrylyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted oxazolyl group, Substituted or unsubstituted thiazolyl group, substituted or unsubstituted oxadiazolyl group, substituted or unsubstituted
티아디아졸일기， 치환 또는 비치환된 피리딜기, 치환 또는 비치환된 피리미디닐기, 치환 또는 비치환된 피라지닐기, 치환 또는 비치환된 트리아지닐기, 치환 또는 비치환된 벤조퓨라닐기, 치환 또는 비치환된 벤조티오페닐기， 치환 또는 비치환된 벤즈이미다졸일기, 치환 또는 비치환된 인돌일기， 치환 또는 비치환된 퀴놀리날기, 치환 또는 비치환된 이소퀴놀리닐기, 치환 또는 비치환된 퀴나졸리닐기, 치환또는 비치환된 퀴녹살리닐기, 치환 또는 비치환된 나프티리디닐기, 치환 또는 비치환된 벤즈옥사진일기， 치환 또는 비치환된 벤즈티아진일기, 치환 또는 비치환된 Thiadiazolyl group, substituted or unsubstituted pyridyl group, substituted or unsubstituted pyrimidinyl group, substituted or unsubstituted pyrazinyl group, substituted or unsubstituted triazinyl group, substituted or unsubstituted benzofuranyl group, substituted Or unsubstituted benzothiophenyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted indolyl group, substituted or unsubstituted quinolinal group, substituted or unsubstituted isoquinolinyl group, substituted or unsubstituted A quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzthiazinyl group, a substituted or unsubstituted
아크리디닐기, 치환 또는 비치환된 페나진일기, 치환 또는 비치환된 페노티아진일기， 치환 또는 비치환된 페녹사진일기， 치환 또는 비치환된 카바졸일기， 치환 또는 비치환된 디벤조퓨란일기, 또는 치환 또는 비치환된 디벤조티오펜일기, 또는 이들의 조합일 수 있으나, 이에 제한되지는 않는다ᅳ Acridinyl group, substituted or unsubstituted phenazineyl group, substituted or unsubstituted phenthiazineyl group, substituted or unsubstituted phenoxazineyl group, substituted or unsubstituted carbazoleyl group, substituted or unsubstituted dibenzofuranyl group , Or a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof, but is not limited thereto.
본 명세서에서, 정공 특성이란, 전기장 (electric field)을 가했을 때 전자를 공여하여 정공을 형성할 수 있는 특성을 말하는 것으로 , HOMO 준위를 따라 전도 특성을 가져 양극에서 형성된 정공의 발광층으로의 주입, 발광층에서 형성된 정공의 양극으로의 이동 및 발광층에서의 이동을 용이하게 하는 특성을 의미한다. In the present specification, the hole characteristic refers to a characteristic capable of forming holes by donating electrons when an electric field is applied, and injecting holes formed at the anode into the light emitting layer having conductive properties along the HOMO level, and emitting layer. It refers to a property that facilitates the movement of the hole formed in the anode and movement in the light emitting layer.
또한 전자 특성이란， 전기장을 가했을 때 전자를 받을 수 있는 특성을 말하는 것으로， LUMO 준위를 따라 전도 특성을 가져 음극에서 형성된 전자의 발광층으로의 주입, 발광층에서 형성된 전자의 음극으로의 이동 및 발광층에서의 이동을 용이하게 하는 특성을 의미한다. 이하 일 구현예에 따른 유기 광전자 소자를 설명한다. In addition, the electron characteristic refers to a characteristic in which electrons can be received when an electric field is applied, and has a conductivity characteristic along the LUMO level, injecting electrons formed at the cathode into the light emitting layer, moving electrons formed in the light emitting layer to the cathode, and It means a property that facilitates movement. Hereinafter, an organic optoelectronic device according to an embodiment is described.
상기 유기 광전자 소자는 전기 에너지와 광 에너지를 상호 전환할 수 있는
소자이면 특별히 한정되지 않으며, 예컨대 유기 광전 소자, 유기 발광 소자, 유기 태양 전지 및 유기 감광체 드럼 등을 들 수 있다. The organic optoelectronic device may switch between electrical energy and light energy. It will not specifically limit, if it is an element, For example, an organic photoelectric element, an organic light emitting element, an organic solar cell, an organic photosensitive drum, etc. are mentioned.
여기서는 유기 광전자 소자의 일 예인 유기 발광 소자를 도면을 참고하여 설명한다. Herein, an organic light emitting diode as an example of an organic optoelectronic device will be described with reference to the drawings.
도 1 및 도 2는 일 구현예에 따른 유기 발광 소자를 보여주는 단면도이다. 도 1을 참고하면， 일 구현예에 따른 유기 발광 소자 (100)는 서로 마주하는 양극 (120)과 음극 (110)， 그리고 양극 (120)과 음극 (1 10) 사이에 위치하는 유기층 (105)을 포함한다ᅳ . 1 and 2 are cross-sectional views illustrating an organic light emitting diode according to an embodiment. Referring to FIG. 1, an organic light emitting diode 100 according to an embodiment includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 positioned between the anode 120 and the cathode 1 10. It includes ᅳ.
양극 (120)은 예컨대 정공 주입이 원활하도톡 일 함수가 높은 도전체로 만들어질 수 있으며, 예컨대 금속, 금속 산화물 및 /또는 도전성 고분자로 만들어질 수 있다. 양극 (120)은 예컨대 니켈， 백금， 바나듐， 크롬， 구리, 아연， 금과 같은 금속 또는 이들의 합금; 아연산화물, 인듐산화물， 인듐주석산화물 (ITO), The anode 120 may be made of, for example, a conductor having a high hole function, for example, to facilitate hole injection, and may be made of, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 120 is, for example, a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold or an alloy thereof; Zinc oxide, indium oxide, indium tin oxide (ITO),
인듐아연산화물 (IZO)과 같은 금속 산화물; ZnO와 A1 또는 Sn02와 Sb와 같은 금속과 산화물의 조합; 폴리 (3-메틸티오펜)， 폴리 (3,4- (에틸렌— 1,2- 디옥시)티오펜 )(polyehtylenedioxythiophene: PEDT), 폴리피를 및 폴리아닐린과 같은 도전성 고분자 등을 들 수 있으나, 이에 한정되는 것은 아니다. Metal oxides such as indium zinc oxide (IZO); Combinations of oxides with metals such as ZnO and A1 or Sn0 2 and Sb; Conductive polymers such as poly (3-methylthiophene), poly (3,4- (ethylene- 1,2-dioxy) thiophene) (polyehtylenedioxythiophene: PEDT), polypyrrole and polyaniline, and the like. It is not limited.
음극 (110)은 예컨대 전자 주입이 원활하도록 일 함수가 낮은 도전체로 만들어질 수 있으며, 예컨대 금속， 금속 산화물 및 /또는 도전성 고분자로 만들어질 수 있다. 음극 (110)은 예컨대 마그네슴， 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬， 가돌리늄， 알루미늄, 은, 주석, 납, 세슴, 바륨 등과 같은 금속 또는 이들의 합금; LiF/Al, LiC¾/Al, LiF/Ca, LiF/Al 및 BaF2/Ca과 같은 다층 구조 물질을 들 수 있으나, 이에 한정되는 것은 아니다. The cathode 110 may be made of a low work function conductor, for example, to facilitate electron injection, and may be made of metal, metal oxide and / or conductive polymer, for example. Cathode 110 is, for example, a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, sesame, barium, or an alloy thereof; Multi-layered materials such as LiF / Al, LiC¾ / Al, LiF / Ca, LiF / Al, and BaF 2 / Ca, but are not limited thereto.
유기층 (105)은 정공 주입층， 정공 수송층， 전자 주입층 및 전자 수송층 중 적어도 하나를 포함하는 보조층, 및 발광층 (130)을 포함한다. The organic layer 105 includes an auxiliary layer including at least one of a hole injection layer, a hole transport layer, an electron injection layer, and an electron transport layer, and a light emitting layer 130.
도 2는 다른 구현예에 따른 유기 발광 소자를 보여주는 단면도이다. 2 is a cross-sectional view illustrating an organic light emitting device according to another embodiment.
도 2를 참고하면， 유기 발광 소자 (200)는 발광층 (130) 외에 정공 보조층 (140)을 더 포함한다. 정공 보조층 (140)은 양극 (120)과 발광층 (130) 사이의 정공 주입 및 /또는 정공 이동성을 더욱 높이고 전자를 차단할 수 있다. 정공 보조충 (140)은 예컨대 정공 수송충， 정공 주입층 및 /또는 전자 차단층일 수 있으며， 적어도 1층을 포함할 수 있다.
도 1 또는 도 2의 유기층 (105)은 도시하지는 않았지만, 전자주입층, 전자수송층, 전자수송보조층, 정공수송층, 정공수송보조층, 정공주입층 또는 이들의 조합층을 추가로 더 포함할 수 있다. Referring to FIG. 2, the organic light emitting diode 200 further includes a hole auxiliary layer 140 in addition to the light emitting layer 130. The hole auxiliary layer 140 may further increase hole injection and / or hole mobility between the anode 120 and the light emitting layer 130 and block electrons. The hole auxiliary layer 140 may be, for example, a hole transport layer, a hole injection layer, and / or an electron blocking layer, and may include at least one layer. Although not shown, the organic layer 105 of FIG. 1 or 2 may further include an electron injection layer, an electron transport layer, an electron transport auxiliary layer, a hole transport layer, a hole transport auxiliary layer, a hole injection layer, or a combination thereof. have.
유기 발광 소자 (100, 200)는 기판 위에 양극 또는 음극을 형성한후， 진공증착법 (evaporation), 스퍼터링 (sputtering), 플라즈마 도금 및 이온도금과 같은 건식성막법； 또는 스핀코팅 (spin coating), 침지법 (dipping), 유동코팅법 (flow coating)과 같은 습식성막법 등으로 유기층을 형성한 후， 그 위에 음극 또는 양극을 형성하여 제조할 수 있다. ' 일 구현예에 따른 유기 광전자 소자는, 서로 마주하는 양극과 음극, 그리고 상기 양극과 상기 음극 사이에 위치하는 유기층을 포함하고, 상기 유기층은 정공 주입층, 정공 수송층, 전자 주입층 및 전자 수송층 중 적어도 하나를 포함하는 보조층, 및 발광층을 포함하며, 상기 발광층은 하기 화학식 1로 표현되는 제 1 호스트， 하기 화학식 2 및 화학식 3의 조합으로 표현되는 거 12 호스트, 및 최대 발광 파장이 550 nm 내지 750 nm인 인광 도편트를 포함한다. 화학식 1] [화학식 2] [화학식 3] The organic light emitting diodes 100 and 200 may be formed by forming an anode or a cathode on a substrate, followed by a dry film method such as evaporation, sputtering, plasma plating, and ion plating; or spin coating or needle coating. After forming the organic layer by a wet film method such as dipping, flow coating, or the like, it may be prepared by forming a cathode or an anode thereon. The organic optoelectronic device according to the embodiment includes an anode and a cathode facing each other, and an organic layer positioned between the anode and the cathode, wherein the organic layer is a hole injection layer, a hole transport layer, an electron injection layer, and an electron transport layer. And an auxiliary layer including at least one, and a light emitting layer, wherein the light emitting layer comprises: a first host represented by the following Chemical Formula 1; a 12 host represented by a combination of the following Chemical Formulas 2 and 3; Phosphorescent dopants that are 750 nm. Formula 1] [Formula 2 ] [Formula 3]
상기 화학식 1에서, In Chemical Formula 1,
X1는 Ο 또는 S이고, X 1 is Ο or S,
Ζ1 내지 Ζ3은 각각 독립적으로 Ν 또는 CRa이고 Ζ 1 to Ζ 3 are each independently Ν or CR a and
Z1 내지 Z3 중 적어도 둘은 N이고, At least two of Z 1 to Z 3 are N,
L1 내지 L3은 각각 독립적으로 단일결합, 또는 치환 또는 비치환된 C6 내지 C20 아릴렌기이고, L 1 to L 3 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,
A1 및 A2는 각각 독립적으로 치환 또는 비치환된 C6 내지 C30 아릴기, 또 τ 치환 또는 비치환된 C2 내지 C30헤테로고리기이고,
A1 및 A2 중 적어도 하나는 치환 또는 비치환된 C6 내지 C30 아릴기이고, Ra 및 R1 내지 R3은 각각 독립적으로 수소， 중수소， 시아노기， 치환 또는 비치환된 C1 내자 C10 알킬기, 또는 치환 또는 비치환된 C6 내지 C20 아릴기이며; 상기 화학식 2 및 3에서, A 1 and A 2 are each independently a substituted or unsubstituted C6 to C30 aryl group, and a τ substituted or unsubstituted C2 to C30 heterocyclic group, At least one of A 1 and A 2 is a substituted or unsubstituted C6 to C30 aryl group, R a and R 1 to R 3 are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 internal C10 alkyl group, Or a substituted or unsubstituted C6 to C20 aryl group; In Chemical Formulas 2 and 3,
Ar2는 치환 또는 비치환된 C6 내지 C20 아릴기이고, Ar 2 is a substituted or unsubstituted C6 to C20 aryl group,
화학식 2의 인접한 2개의 *은 화학식 3과 연결되고, Two adjacent * of Formula 2 are linked to Formula 3,
화학식 3과 연결되지 않은 화학식 2의 *은 각각 독립적으로 C-La-Rb이고, V, Y1 및 Y2는 각각 독립적으로 단일결합, 또는 치환 또는 비치환된 C6 내지 C20 아릴렌기이고, * Of Formula 2, which is not linked to Formula 3, is each independently CL a -R b , and V, Y 1 and Y 2 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,
Rb 및 R6 내지 R12는 각각 독립적으로 수소, 중수소, 시아노기, 치환 또는 비치환된 C1 내지 C10 알킬기, 또는 치환 또는 비치환된 C6 내지 C20 아릴기이다. 본 발명에 따른 유기 광전자 소자는， 제 1 호스트로서 디벤조퓨란 (또는 디벤조티오펜)이 트리아진 또는 피리미딘 모이어티에 결합하는 구조를 포함함으로써 LUMO의 확장 및 ET 모이어티의 평면성 확장을 통하여 정공 및 전자의 주입 속도를 증가시킬 수 있다. 또한, 상기 트리아진 /피리미딘의 치환기로 나프틸기 등의 융합된 아릴 또는 융합된 헤테로아릴 구조가 도입될 경우 분자의 평면성이 증가하면서 Ti stacking을 높여 결과적으로는 전하의 이동이 용이해져 구동， 수명， 효율 특성이 더 좋은 소자를 구현하는데 더 유리하다ᅳ R b and R 6 to R 12 are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C20 aryl group. The organic optoelectronic device according to the present invention comprises a structure in which dibenzofuran (or dibenzothiophene) binds to a triazine or pyrimidine moiety as a first host, thereby expanding the LUMO and the planar expansion of the ET moiety. And an injection speed of electrons. In addition, when a fused aryl or fused heteroaryl structure such as a naphthyl group is introduced as the substituent of the triazine / pyrimidine, the planarity of the molecule is increased and the Ti stacking is increased. ， It is more advantageous to realize the device with better efficiency characteristics.
특히, 제 2 호스트로서 나프틸기가 치환된 인돌로카바졸을 도입함으로써, 비융합아릴만을 갖는 구조 대비 HOMO 전자 구름이 확장되고, hole의 hopping에 유리한 구조를 갖게 되어, 결과적으로 높은 정공이동도 및 분자량 대비 높은 유리전이온도와 열 안정성을 확보할 수 있어 , 최대 발광 파장이 550 nm 내지 750 nm인 적색 영역에서 장수명의 특성이 구현될 수 있다. In particular, by introducing indolocarbazole substituted with a naphthyl group as the second host, the HOMO electron cloud is expanded in comparison with the structure having only the non-fused aryl, and has a structure favorable for hopping of the hole, resulting in high hole mobility and High glass transition temperature and thermal stability compared to the molecular weight can be ensured, the long life characteristics can be realized in the red region of the maximum emission wavelength of 550 nm to 750 nm.
본 발명의 일 실시예에서 , ζ1 내지 Ζ3은 모두 Ν일 수 있다. In one embodiment of the present invention, ζ 1 to Ζ 3 may be all N.
본 발명의 일 실시예에서, R1 내지 R3은 각각 독립적으로 수소 또는 페닐기 일 수 있다. In one embodiment of the present invention, R 1 to R 3 may be each independently hydrogen or a phenyl group.
본 발명의 일 실시예에서, 상기 화학식 1의 Α1 및 Α2는 각각 독립적으로， 치환 또는 비치환된 C6 내지 C30 아릴기， 또는 치환 또는 비치환된 C2 내지 C30 헤테로고리기이고， Α1 및 Α2 중 어느 하나는 치환 또는 비치환된 C6 내지 C30 아릴기이다.
본 발명의 구체적인 일 실시예에서, 상기 A1은 치환 또는 비치환된 C6 내지 C30 아릴기이고, 상기 A2는 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C2 내지 C30 헤테로고리기일 수 있다. In one embodiment of the present invention, A 1 and A 2 of Formula 1 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group, A 1 and Any one of A 2 is a substituted or unsubstituted C 6 to C 30 aryl group. In a specific embodiment of the present invention, A 1 is a substituted or unsubstituted C6 to C30 aryl group, A 2 is a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 hetero It may be a ring group.
본 발명의 더욱 구체적인 일 실시예에서, 상기 A1은 치환 또는 비치환된 C6 내지 C20 아릴기일 수 있고, 상기 A1은 예컨대 치환 또는 비치환된 페닐기, 치환 또는 비치환된 바이페닐기 , 치환 또는 비치환된 터페닐기 , 치환 또는 비치환된 쿼터페닐기, 또는 치환 또는 비치환된 나프틸기일 수 있으며， 상기 화학식 1은 하기 화학식 1_ I으로 표현될 수 있다.In a more specific embodiment of the present invention, A 1 may be a substituted or unsubstituted C6 to C20 aryl group, wherein A 1 is, for example, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted group. It may be a substituted terphenyl group, a substituted or unsubstituted quarterphenyl group, or a substituted or unsubstituted naphthyl group, wherein Formula 1 may be represented by the following Formula 1_I.
화학식 1- 1 ] Formula 1-1]
상기 화학식 1- 1에서, Χ', Ζ1 내지 Ζ3,∑ 내지 L3, A2, 및 R1 내지 R3의 정의는 전술한 바와 같고, R4 및 R5의 정의는 전술한 R1 내지 R3의 정의와 같다. In the general formula 1- 1, Χ ', Ζ 1 to 3 Ζ, Σ to L 3, A 2, and the definitions of R 1 to R 3 are as defined above, R 4 and R 5 are defined in the foregoing R 1 To R 3 .
상기 화학식 1의 A1은 예컨대 하기 그룹 I에 나열된 치환기에서 선택될 수 그룹 I A 1 of Formula 1 may be selected from the substituents listed in Group I below, for example.
상기 그룹 I에서, *은 L2와의 연결 지점이다. In group I, * is the point of attachment to L 2 .
한편, 상기 A2는 치환 또는 비치환된 페닐기, 치환 또는 비치환된 바이페닐기 치환또는 비치환된 나프틸기, 치환 또는 비치환된 터페닐기, 치환 또는 비치환된 쿼터페닐기, 치환 또는 비치환된 디벤조퓨란일기, 치환 또는 비치환된 On the other hand, A 2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted quarterphenyl group, a substituted or unsubstituted di Benzofuranyl group, substituted or unsubstituted
디벤조티오펜일기, 치환또는 비치환된 피리미디닐기， 또는 치환 또는 비치환된 트리아지닐기일 수 있고,
특히, 상기 A2의 구체적인 종류에 따라 상기 제 1 호스트는 하기 화학식 1-1-1 내지 화학식 1-1-3 중 어느 하나로 표현될 수 있다. Dibenzothiophenyl group, substituted or unsubstituted pyrimidinyl group, or substituted or unsubstituted triazinyl group, In particular, the first host may be represented by any one of the following Chemical Formulas 1-1-1 to 1-1-3 according to the specific type of A 2 .
1- I -1] [화학식 1- I -2] 화학식 1- I -3] 1-I -1] [Formula 1-I -2]
상기 화학식 1_I_1 내지 화학식 1- I -3에서, χ^ζ1 내지 ζ3,ι 내지 L R1 내지 R5의 정의는 전술한 바와 같고, X2는 전술한 X1의 정의와 같고 ,Ζ4 내지 Ζ6은 전술한 Ζ1 내지 Ζ3의 정의와 같으며, RC,RD 및 RE의 정의는 전술한 R1 내지 R5의 정의와 같다. In Formula 1_I_1 to Formula 1-I- 3 , the definitions of χ ^ ζ 1 to ζ 3 , ι to LR 1 to R 5 are as described above, X 2 is the same as the definition of X 1 described above, and Ζ 4 to X 6 is the same as the definition of X 1 to X 3 described above, and R C , R D and R E are the same as the definition of R 1 to R 5 described above.
또한， 상기 화학식 1-1-1의 Ar1은 치환 또는 비치환된 C6 내지 C20 아릴기일 수 있고， 구체적으로 치환 또는 비치환된 페닐기, 치환 또는 비치환된 바이페닐기, 치환 또는 비치환된 나프틸기， 치환 또는 비치환된 터페닐기， 또는 치환 또는 비치환된 쿼터페닐기일 수 있으며, 이 때 추가 치환기는 중수소, 시아노기， 페닐기， 또는 나프틸기일 수 있다ᅳ In addition, Ar 1 of Formula 1-1-1 may be a substituted or unsubstituted C6 to C20 aryl group, specifically substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted naphthyl group , A substituted or unsubstituted terphenyl group, or a substituted or unsubstituted quarterphenyl group, wherein the additional substituent may be a deuterium, cyano group, phenyl group, or naphthyl group.
본 발명의 구체적인 일 실시예에서， 화학식 1-1-3 중 RC 및 RD은 각각 독립적으로 치환 또는 비치환된 C6 내지 C20아릴기일 수 있으며, 보다 구체적으로 페닐기， 바이페닐기, 나프틸기 또는 터페닐기일 수 있다. In a specific embodiment of the present invention, R C and R D in Formula 1-1-3 may each independently be a substituted or unsubstituted C6 to C20 aryl group, more specifically a phenyl group, a biphenyl group, a naphthyl group or ter It may be a phenyl group.
상기 화학식 1의 A2는 예컨대 하기 그룹 Π에 나열된 치환기에서 선택될 수 있다.
A 2 of Formula 1 may be selected from, for example, the substituents listed in the following group Π.
[그룹 π]
[Group π]
상기 그룹 Π에서， *은 L3와의 연결 지점이다. In the group Π, * is the point of attachment to L 3 .
본 발명의 가장 구체적인 일 실시예에서, 상기 게 1 호스트는 상기 화학식 1-- 1-1 또는 화학식 1-1 -2로 표현될 수 있고, 이 때 R4 및 R5는 예컨대 각각 In the most specific embodiment of the present invention, the Crab 1 host may be represented by Formula 1-1-1 or Formula 1-1-2, wherein R 4 and R 5 are each, for example,
독립적으로 수소, 중수소, 시아노기, 페닐기, 또는 바이페닐기일 수 있고， 상기 화학식 l-1-l의 Ar1은 예컨대 치환 또는 비치환된 페닐기, 치환 또는 비치환된 바이페닐기， 치환 또는 비치환된 나프틸기 또는 치환또는 비치환된 터페닐기일 수 있고, 상기 화학식 1-1 -2의 X2는 0 또는 S이며, Rc,Rd 및 Re는 각각 독립적으로, 수소, 중수소, 시아노기 또는 페닐기일 수 있다. Independently may be hydrogen, deuterium, cyano group, phenyl group, or biphenyl group, wherein Ar 1 of Formula l-1-l is, for example, substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted It may be a naphthyl group or a substituted or unsubstituted terphenyl group, X 2 of Formula 1-1 -2 is 0 or S, R c , R d and R e are each independently hydrogen, deuterium, cyano group or It may be a phenyl group.
한편， 상기 화학식 1-1은 디벤조퓨란일기 (또는 디벤조티오펜일기)의 구체적인 치환 위치에 따라 하기 화학식 1-IA, 화학식 1-IB, 화학식 1-1 C 및 화학식 1-ID 중 어느 하나로 표현될 수 있다. Meanwhile, Chemical Formula 1-1 may be any one of the following Chemical Formula 1-IA, Chemical Formula 1-IB, Chemical Formula 1-1 C, and Chemical Formula 1-ID according to the specific substitution position of the dibenzofuranyl group (or dibenzothiophenyl group). Can be expressed.
[화학식 1- I A] [화학식 1- I B] [Formula 1-I A] [Formula 1-I B]
상기 화학식 1-iA내지 화학식
내지 ζ3,ι 내지 I R1 내지Formula 1-iA to Formula To ζ 3 , ι to IR 1 to
R5찢 A2의 정의는 전술한 바와 같다. The definition of R 5 tear A 2 is as described above.
본 발명의 구체적인 일 실시예에서, 상기 화학식 1-1은 상기 화학식 1-IB로 표현될 수 있으며, 더욱 구체적인 일 에서, 상기 화학식 1-IB은 하기 화학식 1- I B-1 내지 화학식 1-1 B-3 중 어느 하나로 표현될 수 있다. 1- I B-1] [화학식 1- I B-2] In one specific embodiment of the present invention, Chemical Formula 1-1 may be represented by Chemical Formula 1-IB, and more specifically, Chemical Formula 1-IB may be represented by Chemical Formulas 1-I B-1 to Chemical Formula 1-1 It can be represented by any one of B-3. 1- I B-1] [Formula 1- I B-2]
상기 화학식 1-IB-1 내지 화학식 1-IB-3에서, X1 및 Χ^,Ζ1 내지 Z6, L1 내지 L3, Ar1, Rc, Rd, Re 및 R1 내지 R5와정의는 전술한 바와 같다. In Formulas 1-IB-1 to 1-IB-3, X 1 and Χ ^, Ζ 1 to Z 6 , L 1 to L 3 , Ar 1 , R c , R d , R e, and R 1 to R 5 Definitions are as described above.
더욱 구체적인 일 실시예에서, 상기 화학식 1-1 B-1 또는 상기 화학식 1-IB- 2가 바람직하다. In a more specific embodiment, the formula 1-1 B-1 or the formula 1-IB-2 is preferred.
구체적인 일 실시예에서 본 발명의 화학식 1-IB-3의 Rc 및 Rd은 독립적으로 치환 또는 비치환된 C6 내지 C20 아릴기일 수 있으며, 보다 구체적으로 페닐기,
바이페닐기, 나프틸기 또는 터페닐기일 수 있다. 본 발명의 가장 구체적인 일 실시예에서, 상기 L1 내지 L3은 각각 독립적으로 단일 결합이거나 치환 또는 비치환된 페닐렌기, 치환 또는 비치환된 바이페닐렌기， 치환 또는 비치환된 터페닐렌기, 또는 치환 또는 비치환된 나프틸레닐렌기일 수 있고, 예컨대 하기 그룹 m에 나열된 연결기에서 선택될 수 있다. In one specific embodiment, R c and R d of Chemical Formula 1-IB-3 of the present invention may be independently a substituted or unsubstituted C6 to C20 aryl group, more specifically a phenyl group, It may be a biphenyl group, a naphthyl group, or a terphenyl group. In one specific embodiment of the present invention, L 1 to L 3 are each independently a single bond or a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, or It may be a substituted or unsubstituted naphthyleneylene group, for example, it may be selected from the linking groups listed in the group m below.
상기 그룹 m에서, *은 연결 지점이다. In the group m, * is the point of attachment.
더욱 구체적인 일 실시예에서, 상기 L1 내지 L3은 각각 독립적으로 단일 결합이거나 비치환된 페닐렌기일 수 있다. 보다 구체적으로 L1 은 단일 결합이거나 비치환된 페닐렌기일 수 있으나, 단일 결합이 보다 바람직하다. 또한, 본 발명의 더욱 구체적인 일 실시예에서， 상기 화학식 1- 1 -1은 하기 화학식 1- 1 -la또는 화학식 1- I -lb로 표현될 수 있고,In one more specific embodiment, L 1 to L 3 may be each independently a single bond or an unsubstituted phenylene group. More specifically, L 1 may be a single bond or an unsubstituted phenylene group, but a single bond is more preferable. In addition, in a more specific embodiment of the present invention, Formula 1-1 -1 may be represented by the following Formula 1-1 -la or Formula 1-I -lb,
화학식 i_ I -la] [화학식 1- I -lb] Formula i_ I -la] [Formula 1-I -lb]
상기 화학식 1- I -2는 하기 화학식 1- I -2a로 표현될 수 있으며 Formula 1-I-2 may be represented by the following Formula 1-I-2a
[화학식 1- I -2a] [Formula 1-I-2a]
1- I -3a] [화학식 1- I -3b] [화학식 1- I -3c] 1-I -3a] [Formula 1-I -3b]
[ 1 I -3d] [화학식 1- I -3e] [화학식 1 I -3f] [1 I-3d] [Formula 1-I-3e] [Formula 1 I-3f]
상기 화학식 1—1 -la, 화학식 1- 1 -lb, 화학식 1- 1 -2a, 및 화학식 1- I -3a내지 화학식 1- I -3f에서, X^ L1 내지 L3, Rc, Rd, Re 및 R1 내지 R5의 정의는 전술한바와 같다. In Formula 1-1 -la, Formula 1-1 -lb, Formula 1-1-2a, and Formula 1-1-3a to Formula 1-I-3f, X ^ L 1 to L 3 , R c , R The definitions of d , R e and R 1 to R 5 are as described above.
예컨대, 상기 화학식 1- I -la, 화학식 1- I -lb, 화학식 1- I -2a, 및 화학식 1- I - 3a내지 화학식 l- I -3f의 R1 내지 R3은 각각 독립적으로 수소, 중수소, 페닐기, 또는 바이페닐기일 수 있고, R4 및 R5는 각각 독립적으로 수소, 중수소, 페닐기, 바이페닐기, 또는 터페닐기일 수 있고, 더욱 좋게는 R1 내지 R3은 모두 수소이고， R4 및 R5는 각각 독립적으로 수소, 페닐기, 또는 바이페닐기일 수 있다. For example, R 1 to R 3 of Formula 1-I-la, Formula 1-I-lb, Formula 1-I-2a, and Formulas 1-I-3a to l-I-3f are each independently hydrogen, Deuterium, phenyl group, or biphenyl group, R 4 and R 5 may each independently be hydrogen, deuterium, phenyl group, biphenyl group, or terphenyl group, more preferably R 1 to R 3 are all hydrogen, R 4 and R 5 may be each independently hydrogen, a phenyl group, or a biphenyl group.
또한, 상기 화학식 1의 Z1 내지 Z3으로 이루어진 함질소 6각환은 In addition, the nitrogen-containing hexagonal ring consisting of Z 1 to Z 3 of the formula (1)
피리미디닐기， 또는 트리아지닐기일 수 있으며, 더욱 좋게는 트리아지닐기일 수 있다. It may be a pyrimidinyl group or a triazinyl group, and more preferably, it may be a triazinyl group.
본 발명의 구체적인 일 실시예에서, 상기 제 1 호스트는 예컨대 상기 화학식
1-1-1 또는 화학식 1-1-2로 표현될 수 있고, 더욱 좋게는 상기 화학식 1-1 -la, 상기 화학식 1- I .lb 및 상기 화학식 1- I -2a로 표현될 수 있다. In a specific embodiment of the invention, the first host is for example the formula It may be represented by 1-1-1 or formula 1-1-2, and more preferably may be represented by the formula 1-1 -la, the formula 1-1 I.lb and the formula 1-1 I-2a.
또한, 상기 게 1 호스트는 예컨대 상기 화학식 1-IB로 표현될 수 있고, 더욱 좋게는 상기 화학식 1-1 B-1 또는 상기 화학식 1-IB-2로 표현될 수 있다. In addition, the crab 1 host may be, for example, represented by Chemical Formula 1-IB, and more preferably, may be represented by Chemical Formula 1-1 B-1 or Chemical Formula 1-IB-2.
상기 제 1 호스트는 예컨대 하기 그룹 1에 나열된 화합물에서 선택될 수 있으나, 이에 한정되는 것은 아니다. The first host may be selected from, for example, the compounds listed in Group 1 below, but is not limited thereto.
[그룹 1] [Group 1]
-1] [A-2] [A-3] [A-4] -1] [A-2] [A-3] [A-4]
-5] [A-6] [A-7] [A-8] -5] [A-6] [A-7] [A-8]
-9] [A-10] [A-11] [A-12] -9] [A-10] [A-11] [A-12]
-13] [A-14] [A-15] [A-16] -13] [A-14] [A-15] [A-16]
[A-17] [A-18] [A-19] [A-20] [A-17] [A-18] [A-19] [A-20]
-9] [B-10] [B-11] [B-12]
-9] [B-10] [B-11] [B-12]
-13] [B-14] [B-15] [B-16]
-13] [B-14] [B-15] [B-16]
[B-21] [B-22] [B-23] [B-24]
[B-21] [B-22] [B-23] [B-24]
83a9aa5 - - . - -
83a9aa5--. --
o o
【9&89a【99£:9sa---- 【9 & 89a 【99 £ : 9sa ----
【a ta【0卜&【69& ----
o
[A t a 【 0卜 & 【 69 & ---- o
_:H kolanaa9---- _ : H ko l anaa9 ----
ela ϋΐεΐ:-【0【〕ώ6^3-- ela ϋΐ ε ΐ : -[0 [] ώ6 ^ 3--
ϋ:-ε- ο ϋ : -ε- ο
0〕
0〕
[C-9] [C-10] [C-11] [C-12]
[C-9] [C-10] [C-11] [C-12]
[C-17] [C-18] [C-19] [C-20]
[C-17] [C-18] [C-19] [C-20]
[C-21] [C-22] [C-23] [C-24]
[C-21] [C-22] [C-23] [C-24]
-a [6ΐ-α] [8i-a] [L\-Q]
-a [6ΐ-α] [8i-a] [L \ -Q]
[9ΐ-α] [si-α] [ i-a] [ει-α]
[9ΐ-α] [si-α] [ia] [ει-α]
[π-α] [ΐΐ-α] [οι-α] [6-α]
[π-α] [ΐΐ-α] [οι-α] [6-α]
L90L\ZmOZ OAV
L90L \ ZmOZ OAV
-25] [D-26] [D-27] [D-28] -25] [D-26] [D-27] [D-28]
본 발명의 일 실시예에서， 상기 제 2 호스트는 화학식 2 및 화학식 3의 융합 위치에 따라 예컨대 하기 화학식 2A, 화학식 2B, 화학식 2C, 화학식 2D, 화학식 2E 및 화학식 2F 중 어느 하나로 표현될 수 있다. In one embodiment of the present invention, the second host may be represented by any one of the following Chemical Formula 2A, Chemical Formula 2B, Chemical Formula 2C, Chemical Formula 2D, Chemical Formula 2E, and Chemical Formula 2F, depending on the fusion position of Chemical Formula 2 and Chemical Formula 3.
2A] [화학식 2B] [화학식 2C] 2A] [Formula 2B] [Formula 2C]
[ 2D] [화학식 2E] [화학식 2F] [2D] [Formula 2E] [Formula 2F]
상기 화학식 2A 내지 화학식 2F에서, In Chemical Formulas 2A to 2F,
Ar2, La, Y1 및 Y2, Rb 및 R6 내지 R12은 전술한 바와 같고, Lal 내지 La4는 전술한 La의 정의와 같으며, Rbl 내지 RM는 전술한 Rb의 정의와 같다.
상기 Ar2는 치환 또는 비치환된 페닐기, 치환 또는 비치환된 바이페닐기 , 치환 또는 비치환된 나프틸기, 치환 또는 비치환된 터페닐기일 수 있다. Ar 2 , L a , Y 1 and Y 2 , R b and R 6 to R 12 are as described above, L al to L a4 are as defined above in L a , and R bl to R M are described above. Same as the definition of R b . Ar 2 may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted terphenyl group.
본 발명의 구체적인 일 실시예에서, 상기 제 2 호스트는 상기 화학식 2C로 표현될 수 있으며， 나프틸기의 치환 지점에 따라 예컨대 하기 화학식 2C-a또는 화학식 2C-b로 표현될 수 있다. In a specific embodiment of the present invention, the second host may be represented by the formula (2C), it may be represented by, for example, the formula 2C-a or 2C-b according to the substitution point of the naphthyl group.
[화학식 2C-a] [화학식 2C-b] [Formula 2C-a] [Formula 2C-b]
상기 화학식 2C-a 및 화학식 2C-b에서 Ar2, Lal, La2, Y1, Y2, Rbl, Rb2 및 R6 내지 R'2의 정의는 전술한 바와 같다. In Formulas 2C-a and 2C-b, Ar 2 , L al , L a2 , Y 1 , Y 2 , R bl , R b2, and R 6 to R ′ 2 are the same as defined above.
본 발명의 더욱 구체적인 일 실시예에서, 상기 게 1 호스트는 상기 화학식 1- In a more specific embodiment of the present invention, the crab 1 host is represented by Chemical Formula 1-
I으로 표현되고, 상기 제 2 호스트는 상기 화학식 2C-a로 표현될 수 있다. It is represented by I, and the second host may be represented by Chemical Formula 2C-a.
더욱 좋게는 상기 게 1 호스트는 상기 화학식 1- 1 B-1 또는 화학식 1- I B-2로 표현될 수 있다. More preferably, the C 1 host may be represented by Chemical Formula 1-1 B-1 or Chemical Formula 1-I B-2.
한편, 상기 화학식 2C-a의 Rbl 및 Rb2, 그리고 R6 내지 R12는 각각 독립적으로 수소， 중수소, 시아노기 , 치환 또는 비치환된 페닐기， 치환 또는 비치환된 On the other hand, R bl and R b2 of Formula 2C-a, and R 6 to R 12 are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted phenyl group, substituted or unsubstituted
바이페닐기이며, It is a biphenyl group,
상기 Lal 및 La2, 그리고 Y1 및 Y2는 각각 독립적으로, 단일결합, 치환 또는 비치환된 para-페닐렌기, 치환 또는 비치환된 meta-페닐렌기， 또는 치환 또는 비치환된 바이페닐렌기일 수 있다. L al and L a2 , and Y 1 and Y 2 are each independently a single bond, a substituted or unsubstituted para-phenylene group, a substituted or unsubstituted meta-phenylene group, or a substituted or unsubstituted biphenylene. It may be a flag.
본 발명의 일 실시예에서, 상기 R6 내지 R9는 각각 독립적으로 수소, 중수소， 시아노기 또는 페닐기일 수 있으며, 모두 수소일 수 있다. In one embodiment of the present invention, R 6 to R 9 may be each independently hydrogen, deuterium, cyano group or phenyl group, all may be hydrogen.
본 발명의 일 실시예에서， 상기 R10내지 R12는 각각 독립적으로 수소, 중수소, 시아노기, 또는 페닐기일 수 있으며, 더욱 구체적으로 수소 또는 페닐기일 수 있다. 본 발명의 일 실시예에서， 상기 Ar2는 치환 또는 비치환된 페닐기, 치환 또는 비치환된 바이페닐기, 치환 또는 비치환된 나프틸기 또는 치환 또는 비치환된 터페닐기일 수 있다. 또한, 본 발명의 구체적인 일 실시예서 상기 Ar2에 추가
치환되는 치환기는 중수소, 시아노기 , 페닐기 또는 나프틸기일 수 있다. In one embodiment of the present invention, R 10 to R 12 may be each independently hydrogen, deuterium, cyano group, or phenyl group, more specifically may be hydrogen or phenyl group. In one embodiment of the present invention, Ar 2 may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group or a substituted or unsubstituted terphenyl group. In addition, in a specific embodiment of the present invention in addition to Ar 2 Substituents to be substituted may be deuterium, cyano group, phenyl group or naphthyl group.
상기 게 2 호스트는 예컨대 하기 그룹 2에 나열된 화합물에서 선택될 수 있으나, 이에 한정되는 것은 아니다. The crab 2 host may be selected from, for example, the compounds listed in Group 2, but is not limited thereto.
[그룹 2] [Group 2]
-1] [HA-2] [HA-3] [HA-4] -1] [HA-2] [HA-3] [HA-4]
-5] [HA-6] [HA-7] [HA-8] -5] [HA-6] [HA-7] [HA-8]
-13] [HA-14] [HA-15] [HA-16] -13] [HA-14] [HA-15] [HA-16]
-17] [HA-18] [HA-19] [HA-20] -17] [HA-18] [HA-19] [HA-20]
[HA-21] [HA-22] [HA-23] [HA-24] [HA-21] [HA-22] [HA-23] [HA-24]
[HB-5] [HB-6] [HB-7] [HB-8]
[HB-5] [HB-6] [HB-7] [HB-8]
-9] [HB- 10] [HB- 11 ] [HB- 12]
-9] [HB-10] [HB-11] [HB-12]
[HB- 13] [HB- 14] [HB- 15] [HB- 16]
[HB- 13] [HB-14] [HB-15] [HB-16]
[HB- 17] [HB- 18] [HB- 19] [HB-20]
[HB- 17] [HB- 18] [HB- 19] [HB-20]
[HB-21 ] [HB-22] [HB-23 ] [HB-24]
[HB-21] [HB-22] [HB-23] [HB-24]
-DH] [L-DK] [9- H] [S- H] -DH] [L-DK] [9-H] [S-H]
-mi\ [ i ε-ΗΗ] [o ε-eH] [6z-mi -mi \ [i ε-ΗΗ] [o ε-eH] [6z-mi
[83-HH] [LZ-QH] [9Z-HH] [ξΖ-QHl [83-HH] [LZ-QH] [9Z-HH] [ξΖ-QHl
686S00/8T0ZaM/X3d L90L\ZmOZ OAV
686S00 / 8T0ZaM / X3d L90L \ ZmOZ OAV
- Η] [ I ε-DH] [0 £- H] [6Ζ- Η] -Η] [I ε-DH] [0 £-H] [6Ζ- Η]
[8Ζ-ΟΗ] [LZ-DR] [9Z-DU] [SZ-DH] [8Ζ-ΟΗ] [LZ-DR] [9Z-DU] [SZ-DH]
[½-DH][£2-DH] [ZZ-DU] [ t Z-DU] [½-DH] [£ 2-DH] [ZZ-DU] [t Z-DU]
[OZ-DU] [6 ΐ -OH] [81 -OH] it \—OH] [OZ-DU] [6 ΐ -OH] [81 -OH] it \ —OH]
- H] [S ΐ -OH] 0 K H] [ £ t -OH] -H] [S ΐ -OH] 0 K H] [£ t -OH]
[Π OH] [ II -OH] [0 K)H] [6- H] [Π OH] [II -OH] [0 K) H] [6- H]
686S00/8T0ZaM/X3d L90L\ZmOZ OAV
686S00 / 8T0ZaM / X3d L90L \ ZmOZ OAV
[91-QH] [SI-CIH] [t/I-CIH] [ei-aH]
[91-QH] [SI-CIH] [t / I-CIH] [ei-aH]
[Zl- R] [U-QH] [OI-CIH] [6— IH]
[Zl- R] [U-QH] [OI-CIH] [6— IH]
-aH] [ -CIH] [9-aH] [S-QH]
-aH] [-CIH] [9-aH] [S-QH]
-DU] [6 ε— Η] [8 ε- H] ε- H]
-DU] [6 ε— Η] [8 ε- H] ε- H]
[9 ε- H] [s ε-:)Η] ε- H] [ ε ε- H] [9 ε- H] [s ε-:) Η] ε- H] [ε ε- H]
686S00/8T0ZaM/X3d L90L\ZmOZ OAV
686S00 / 8T0ZaM / X3d L90L \ ZmOZ OAV
[Z I -3H] [ 11 -3H] [0 ΐ -3H] [6—3H]
[ZI -3H] [11 -3H] [0 ΐ -3H] [6—3H]
[OZ-QH] [61-QH] [8I-QH] [L\-QU] [OZ-QH] [61-QH] [8I-QH] [L \ -QU]
686S00/8I0ZaM/X3d Ζ.90Ζ.ΙΖ/8Ι0Σ O/W
686S00 / 8I0ZaM / X3d Ζ.90Ζ.ΙΖ / 8Ι0Σ O / W
-3Η] [ £Ζ-ΆΉ [ΖΖ-ΆΉ [ ΐ 3"3Η] -3Η] [£ Ζ-ΆΉ [ΖΖ-ΆΉ [ΐ 3 " 3Η]
-ΆΚ 6 ΐ -3Η] [81 -3Η] YL ΐ -3Η] -ΆΚ 6 ΐ -3Η] [81 -3Η] YL ΐ -3Η]
[91 -3Η] [5 ΐ -ΗΗ] [1/ ΐ -3Η] [ £ 1 -3Η] S00/8T0ZaM/X3d L90L\ZmOZ OAV
[91 -3Η] [5 ΐ -ΗΗ] [1 / ΐ -3Η] [£ 1 -3Η] S00 / 8T0ZaM / X3d L90L \ ZmOZ OAV
[Z I -JH] [ Ιΐ -dH] [01 -dH] [6-dH] [Z I -JH] [Ιΐ -dH] [01 -dH] [6-dH]
-dH] [L-iH] [9-iUl [S-JH] -dH] [L-iH] [9-iUl [S-JH]
S S
[017— 3H] [6 £-HH] [8 £"HH] IL "3Η]
[017— 3H] [6 £ -HH] [8 £ " HH] IL " 3Η]
[9 ε-3Η] [ς ε-3Η] [ -3Η] [ ε ε-3Η] [9 ε-3Η] [ς ε-3Η] [-3Η] [ε ε-3Η]
L90L\ZmOZ OAV
L90L \ ZmOZ OAV
[HF- 17] [HF- 18 ] [HF- 19] [HF-20]
[HF- 17] [HF- 18] [HF- 19] [HF-20]
[HF-25] [HF-26] [HF-27] [HF-28]
-33][HF-34][HF-35][HF-36] [HF-25] [HF-26] [HF-27] [HF-28] -33] [HF-34] [HF-35] [HF-36]
상기 게 1 호스트 및 제 2 호스트는 조성물의 형태로 적용될 수 있다. The first host and the second host may be applied in the form of a composition.
즉, 본 발명은 앞서 설명한 하기 화학식 1로 표현되는 제 1 호스트， 하기 화학식 2 및 화학식 3의 조합으로 표현되는 제 2 호스트를 포함하는 적색 인광 호스트용조성물을 제공한다. That is, the present invention provides a red phosphorescent host composition comprising the first host represented by the following Chemical Formula 1, and the second host represented by the combination of the following Chemical Formula 2 and Chemical Formula 3.
본 발명에서 적색은 인광도판트의 최대 발광 파장이 550 nm 내지 750 nm인 범위를 의미한다. 즉, 본 발명의 조성물이 적용된 발광소자의 도판트의 최대발광 파장이 green 영역을 넘어선 장파장 영역을 의마한다 In the present invention, red means a range in which the maximum emission wavelength of the phosphorescent dopant is 550 nm to 750 nm. That is, the maximum emission wavelength of the dopant of the light emitting device to which the composition of the present invention is applied means a long wavelength region beyond the green region.
본 발명의 유기광전자 소자는 최대 발광 파장이 550 nm 내지 750 nm인 인광 도펀트를 포함한다. 즉 최대발광 파장이 green 영역에서 벗어난 인광 도판트를 포함한다. 예를 들어, redish 영역을 의미하는 파장인 최대 발광파장이 560 nm 내지 750 nm 일 수 있으며 , 570 nm 내지 720 nm, 580 nm 내지 700 nm, 590 nm 내지 700 nm, 600 nm 내지 700 nm 등일 수 있다. The organic optoelectronic device of the present invention includes a phosphorescent dopant having a maximum emission wavelength of 550 nm to 750 nm. That is, it includes a phosphorescent dopant whose maximum emission wavelength is out of the green region. For example, the maximum light emission wavelength, which is a wavelength representing a redish region, may be 560 nm to 750 nm, and may be 570 nm to 720 nm, 580 nm to 700 nm, 590 nm to 700 nm, 600 nm to 700 nm, and the like. .
상기 최대 발광 파장이 550 nm 내지 750 nm인 인광도펀트로는 이리듐 (Ir) 착체나, 백금 ( ) 착체일 수 있으며, 백금 (Pt) 착체는 예컨대 하기 화학식 4-1로 표현될 수 있다. 또한 이리듐 (Ir) 착체는 예컨대 하기 화학식 4-2로 표현될 수 있다. The phosphorescent dopant having a maximum emission wavelength of 550 nm to 750 nm may be an iridium (Ir) complex or a platinum () complex, and the platinum (Pt) complex may be represented by, for example, Chemical Formula 4-1. In addition, the iridium (Ir) complex may be represented by, for example, the following Chemical Formula 4-2.
4-1] 4-1]
상기 화학식 4-1에서
X^, Xs, X 및 Χβ는 각각 1A, 1B, 1C 및 ID와 불포화 고리를 형성하는 원소이고, 각각 독립적으로 C 또는 N이고, In Chemical Formula 4-1 X ^, X s , X and Χ β are each an element which forms an unsaturated ring with 1A, 1B, 1C and ID, and are each independently C or N,
1A, IB, 1C 및 ID는 각각 독립적으로， 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C2 내지 C30 헤테로고리기이고, 1A, IB, 1C, and ID are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
ᅳ ΙΛ Ls, Lc, LD, QA, QB, Qc 및 QD는 각각 독립적으로， 단일 결합, O, S, 치환 또는 비치환된 C1 내지 C30 알킬렌기， 치환 또는 비치환된 C2 내지 C30 알케닐렌기 , 치환 또는 비치환된 C6 내지 C30 아릴렌기, 또는 치환 또는 비치환된 C2 내지 C30 헤테로아릴렌기이고， ΙΙΛ L s , L c , L D , Q A , Q B , Q c and Q D are each independently a single bond, O, S, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted A C2 to C30 alkenylene group, a substituted or unsubstituted C6 to C30 arylene group, or a substituted or unsubstituted C2 to C30 heteroarylene group,
RA, RB, Rc및 1^는 각각 독립적으로, 수소, 중수소, 시아노기, 할로겐기， 실란기， 포스핀기， 아민기, 치환 또는 비치환된 C1 내지 C30 알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C2 내지 C30 R A , R B , R c and 1 ^ are each independently hydrogen, deuterium, cyano group, halogen group, silane group, phosphine group, amine group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30
헤테로아릴기이고, Heteroaryl group,
RA, RB, Rc 및 는 각각 독립적으로 존재하거나， 인접한 기끼리 서로 연결되어 고리를 형성하고， R A , R B , R c and are each independently present or adjacent groups are connected to each other to form a ring,
n은 0 내지 5의 정수 중 하나이며， n is one of integers from 0 to 5,
a, b, c 및 d는 각각 독립적으로 0 내지 3의 정수 중 하나이다. a, b, c and d are each independently one of an integer of 0-3.
[화학식 4-2] [Formula 4-2]
상기 화학식 4-2에서， In Chemical Formula 4-2,
2A, 2B 및 2C는 각각 독립적으로 치환 또는 비치환된 벤젠 고리이고, 2A, 2B and 2C are each independently a substituted or unsubstituted benzene ring,
2A, 2B 및 2C 중 적어도 하나는 인접한 착화합물과 융합 고리를 형성하고, RE, RF, RG, RH, R7, RJ및 I ^는 각각 독립적으로， 수소, 중수소， 시아노기， 할로겐기, 실란기, 포스핀기, 아민기， 치환 또는 비치환된 C1 내지 C10 알킬기， 치환 또는 비치환된 C6 내지 C30 아릴기， 또는 치환 또는 비치환된 C2 내지 C30 At least one of 2A, 2B and 2C forms a fused ring with an adjacent complex, and R E , R F , R G , R H , R 7 , R J and I ^ are each independently hydrogen, deuterium, cyano group, Halogen, silane, phosphine, amine, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30
헤테로아릴기이고，
RE, RF, RG, RH, R7, Ry및 는 각각 독립적으로 존재하거나, 인접한 기끼리 서로 연결되어 고리를 형성하고, Heteroaryl group, R E , R F , R G , R H , R 7 , R y and are each independently or adjacent groups are connected to each other to form a ring,
m은 1 내지 3의 정수 중 하나이다. m is one of the integers 1-3.
본 발명의 일 실시예에서, 상기 백금 (Pt) 착체는 하기 화학식 4_l a또는 하기 화학식 4-lb로 표현될 수 있다. In one embodiment, the platinum (Pt) complex may be represented by the following Formula 4 or Chemical Formula la _ 4-lb.
[화학식 4-la] 4-lb] [Formula 4-la] 4-lb]
상기 화학식 4-la 및 화학식 4-lb에서, Xs, Xc, XD, 1A, IB, 1C, ID, LA, LB, Lc, LD, QA, QB, Qc, Q°, R^, RB, Rc, R°, a, b, c 및 d의 정의는 전술한 바와 같다. In Formulas 4-la and 4-lb, X s , X c , X D , 1A, IB, 1C, ID, L A , L B , L c , L D , Q A , Q B , Q c , The definitions of Q °, R ^, R B , R c , R °, a, b, c and d are as described above.
또한, 본 발명의 구체적인 일 실시예에서, 상기 1A, 1B, 1C 및 1D는 각각 독립적으로 치환 또는 비치환된 C6 내지 C20 아릴기， 또는 치환 또는 비치환된 C2 내지 C20 헤테로고리기일 수 있고, 더욱 구체적으로, 치환 또는 비치환된 페닐기 , 치환 또는 비치환된 나프틸기， 치환 또는 비치환된 안트라세닐기 , 치환 또는 비치환된 페난트레닐기, 치환 또는 비치환된 트리페닐레닐기， 치환 또는 비치환된 피리디닐기， 치환 또는 비치환된 벤즈이미다졸릴기, 치환 또는 비치환된 In addition, in one specific embodiment of the present invention, 1A, 1B, 1C and 1D may be each independently a substituted or unsubstituted C6 to C20 aryl group, or a substituted or unsubstituted C2 to C20 heterocyclic group, and more Specifically, substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted triphenylenyl group, substituted or unsubstituted Pyridinyl groups, substituted or unsubstituted benzimidazolyl groups, substituted or unsubstituted
벤조티아졸기， 치환 또는 비치환된 벤즈옥사졸기 , 치환 또는 비치환된 피를릴기， 치환또는 비치환된 피라졸릴기 , 치환 또는 비치환된 이미다졸릴기, 치환 또는 비치환된 옥사졸릴기일 수 있으며， 예컨대 하기 그룹 IV에 나열된 기에서 선택될 수 있으며, 하기 그룹 IV에 나열된 기는 추가로 더 치환될 수 있다.Benzothiazole group, substituted or unsubstituted benzoxazole group, substituted or unsubstituted pyryl group, substituted or unsubstituted pyrazolyl group, substituted or unsubstituted imidazolyl group, substituted or unsubstituted oxazolyl group And may be selected, for example, from the groups listed in Group IV below, and the groups listed in Group IV below may be further substituted.
그룹 IV]
Group IV]
상기 그룹 IV에서, X는 1A, 1B, 1C 및 1D와 불포화 고리를 형성하는 원소이고 각각 독립적으로 C 또는 N이다. 추가 치환기는 중수소, 시아노기， 할로겐기， C1
내지 CIO 알킬기, 또는 C1 내지 C10 플루오로알킬기일 수 있다. In Group IV, X is an element forming an unsaturated ring with 1A, 1B, 1C and 1D and each independently is C or N. Additional substituents are deuterium, cyano, halogen, C1 To CIO alkyl group, or C1 to C10 fluoroalkyl group.
더욱 좋게는, 상기 ΙΑ, ΙΒ, 1C 및 1D는 치환 또는 비치환된 페닐기, 치환 또는 비치환된 피리디닐기， 치환 또는 비치환된 벤즈이미다졸릴기, 치환 또는 비치환된 벤조티아졸기 , 치환 또는 비치환된 피를릴기， 치환 또는 비치환된 피라졸릴기일 수 있다. More preferably, the ΙΑ, ΙΒ, 1C and 1D are substituted or unsubstituted phenyl group, substituted or unsubstituted pyridinyl group, substituted or unsubstituted benzimidazolyl group, substituted or unsubstituted benzothiazole group, substituted Or an unsubstituted pyryl group, a substituted or unsubstituted pyrazolyl group.
본 발명의 구체적인 일 실시예에서, a, b, c 및 d가 2 이상인 경우 치환기 ΚΛ RB, Rc 및 RD는 각각 서로 동일할 수도 있고， 상이할 수도 있다ᅳ In a specific embodiment of the present invention, when a, b, c and d are 2 or more, the substituents ΚΛ R B , R c and R D may be the same as or different from each other.
한편， 본 발명의 구체 실시예는 I^, RS, RC및 R° 중 인접한 기가 융합하여 고리를 형성한 구조도 포함한다. 예컨대 하기 그룹 3의 화합물 3-5, 화합물 3-8과 같은 형태를 예로 들 수 있다. Meanwhile, specific embodiments of the present invention also include a structure in which adjacent groups of I ^, R S , R C and R ° are fused to form a ring. For example, the same form as compound 3-5 of compound 3, compound 3-8 below.
또한, 본 발명의 일 실시예에서, 상기 이리듐 (Ir) 착체는 하기 화학식 4-2a, 또는 화학식 4-2b로 표현될 수 있다. In addition, in one embodiment of the present invention, the iridium (Ir) complex may be represented by the following formula (4-2a), or formula (4-2b).
4-2a] [화학식 4-2b] 4-2a] [Formula 4-2b]
상기 화학식 4-2a 및 화학식 4-2b에서， R RF, RG, RH, RJ, RJ, RK 및 m의 정의는 전술한 바와 같고， R£, RM 및 RW의 정의는 전술한 R£, R 7, RG, R", R7, II·7및 의 정의와 같다. In Formulas 4-2a and 4-2b, the definitions of RR F , R G , R H , R J , R J , R K and m are as described above, and the definitions of R £ , R M and RW are described above. The definitions of R £ , R 7 , R G , R ", R 7 , II · 7 and
본 발명의 구체적인 일 실시예에서， 상기 R£, RF, RG, RH, Rr, RJ, RK, RL, RM및 Rw은 수소， 중수소, 시아노기, 할로겐기, C1 내지 C10 알킬기, 또는 C1 내지 C10 플루오로알킬기일 수 있다. In a specific embodiment of the present invention, R £ , R F , R G , R H , R r , R J , R K , R L , R M and R w are hydrogen, deuterium, cyano group, halogen group, It may be a C1 to C10 alkyl group, or a C1 to C10 fluoroalkyl group.
한편, 본 발명의 구체 실시예는 R£, R , RG, 및 R "중 인접한 기가 융합하여 고리를 형성한 구조도 포함한다. 예컨대 하기 그룹 3의 화합물 4-12와 같은 형태를 예로 들 수 있다. Meanwhile, specific embodiments of the present invention also include a structure in which adjacent groups of R £ , R, R G , and R "are fused to form a ring. For example, a form such as Compound 4-12 of Group 3 may be exemplified. have.
상기 인광 도편트는 예컨대 하기 그룹 3에 나열된 화합물에서 선택될 수 있으나, 이에 한정되는 것은 아니다.
The phosphorescent dopant may be selected from, for example, the compounds listed in Group 3, but is not limited thereto.
ox
ox
[ε-ε][ε-ε][ι-ε] [ε-ε] [ε-ε] [ι-ε]
[ε를 τ:] [τ τ:]
L90L\ZmOZ OAV
L90L \ ZmOZ OAV
[Zrl7][9-t7][S ]뚜] [Zrl7] [9-t7] [S]
L90L\ZmOZ OAV
L90L \ ZmOZ OAV
본 발명의 가장 구체적인 일 실시예에서， 상기 제 1 호스트는 상기 1- 1 B-1 또는 화학식 1- I B-2로 표현되고, 상기 제 2 호스트는 상기 화학식 2C-a로 표현되며， 상기 인광 도펀트는 상기 화학식 4-2a로 표현될 수 있다. In the most specific embodiment of the present invention, the first host is represented by the 1-1 B-1 or Formula 1-1 I-2, the second host is represented by the formula 2C-a, the phosphorescence The dopant may be represented by Chemical Formula 4-2a.
더욱 구체적으로, 상기 제 1 호스트 및 게 2 호스트는 1 :9 내지 5:5, 2:8 내지 5:5 3:7 내지 5:5의 증량비 범위로 포함될 수 있고， 상기 인광 도편트는 상기 제 1 호스트 및 게 2 호스트의 조성물 100 중량0 /。에 대하여 0.1 내지 50 중량0 /0로 포함될 수 있다. 또한, 상기 게 1 호스트 및 제 2 호스트는 3:7 내지 5:5의 중량비 범위로 포함될 수 있고, 상기 인광 도편트는 상기 제 1 호스트 및 제 2 호스트의 조성물 100 중량0 /0에 대하여 0.1 내지 10 중량%로 포함될 수 있다. 가장 구체적으로는 상기 제 1 호스트 및 제 2 호스트는 3:7 또는 5:5의 중량비로 포함될 수 있고， 상기 인광 도편트는 상기 제 1 호스트 및 게 2 호스트의 조성물 100 중량 %에 대하여 0.5 내지 10 중량0 /0로 포함될 수 있다. More specifically, the first host and the crab 2 host may be included in the increase ratio of 1: 9 to 5: 5, 2: 8 to 5: 5 3: 7 to 5: 5, wherein the phosphorescent dopant is 1 and to the host with respect to 100 parts by weight of the composition 0 /. of the second host may be included as 0.1 to 50 wt. 0/0. Furthermore, the crab first host and the second host is 3: 7 to 5: can be included in a weight ratio of from 5, wherein the phosphorescent dopyeon teuneun for the first host and a composition of 100 parts by weight 0/0 of the second host from 0.1 to 10 It may be included in weight percent. Most specifically, the first host and the second host may be included in a weight ratio of 3: 7 or 5: 5, the phosphorescent dopant is 0.5 to 10% by weight based on 100% by weight of the composition of the first host and the crab 2 host It may include 0/0.
다른 일 구현예에 따른 적색 인광 호스트용 조성물은 상기 화학식 1로 표현되는 제 1 호스트, 그리고 상기 화학식 2 및 화학식 3의 조합으로 표현되는 저】2 호스트를 포함할 수 있다. The red phosphorescent host composition according to another embodiment may include a first host represented by Chemical Formula 1 and a low] 2 host represented by a combination of Chemical Formulas 2 and 3.
본 발명의 일 실시예에서， 상기 제 1 호스트는 상기 화학식 1- 1로 표현될 수 있고, 상기 게 2 호스트는 상기 화학식 2C로 표현될 수 있다. In one embodiment of the present invention, the first host may be represented by Chemical Formula 1-1, and the second host may be represented by Chemical Formula 2C.
본 발명의 구체적인 일 실시예에서， 상기 게 1 호스트는 상기 화학식 1- 1 B-1 또는 화학식 1- I B-2로 표현될 수 있으며， 이 때 상기 화학식 1- I B-1의 Ar1은 치환 또는 비치환된 페닐기, 치환 또는 비치환된 바이페닐기, 치환 또는 비치환된 나프틸기, 치환 또는 비치환된 터페닐기, 또는 치환 또는 비치환된 쿼터페닐기일 수 있다. 기타 치환기의 정의는 전술한 바와 같다. In a specific embodiment of the present invention, the crab 1 host may be represented by Formula 1-1 B-1 or Formula 1-I B-2, wherein Ar 1 of Formula 1-I B- 1 is It may be a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted quarterphenyl group. The definition of other substituents is as described above.
전술한 유기 발광 소자는 유기 발광 표시 장치에 적용될 수 있다.
【발명의 실시를 위한 형태】 The organic light emitting diode described above may be applied to an organic light emitting display device. [Form for implementation of invention]
이하에서는 본 발명의 구체적인 실시예들을 제시한다. 다만， 하기에 기재된 실시예들은 본 발명을 구체적으로 예시하거나 설명하기 위한 것에 불과하며， 이로서 본 발명이 제한되어서는 아니된다. The following presents specific embodiments of the present invention. However, the embodiments described below are merely for illustrating or explaining the present invention in detail, and thus the present invention is not limited thereto.
이하， 실시예 및 합성예에서 사용된 출발물질 및 반웅물질은 특별한 언급이 없는 한, Sigma— Aldrich社 또는 TCI 社에서 구입하였거나, 공지된 방법을 통해 합성하였다. 본 발명의 화합물의 보다 구체적인 예로서 제시된 화합물을 하기 단계를 통해 합성하였다. Hereinafter, starting materials and reaction materials used in Examples and Synthesis Examples were purchased from Sigma—Aldrich or TCI, or synthesized through known methods, unless otherwise specified. Compounds given as more specific examples of the compounds of the present invention were synthesized through the following steps.
(제 1 호스트의 제조) (Manufacture of the First Host)
합성예 1 : 화합물 B-1의 합성 Synthesis Example 1 Synthesis of Compound B-1
a) 중간체 B-1-1의 합성 a) Synthesis of Intermediate B-1-1
500 mL 둥근바닥플라스크에 시아누릭클로라이드 15 g(81.34 mmol)을 무수 테트라하이드로퓨란 200 mL에 녹이고， 질소대기하에서 3-바이페닐 Dissolve 15 g (81.34 mmol) of cyanuric chloride in 200 mL of anhydrous tetrahydrofuran in a 500 mL round bottom flask, and 3-biphenyl under nitrogen atmosphere.
마그네슘브로마이드 용액 (0.5M 테트라하이드로퓨란 ) 1 당량을 0°C에서 적가하고 서서히 상온으로 을린다. 상온에서 1 시간 동안 교반한 후， 반웅액을 얼음물 500 mL에 넣고 층분리시킨다. 유기층을 분리하고 무수 황산마그네슘을 처리하고 농축한다. 농축된 잔사를 테트라하이드로퓨란과 메탄올로 재결정하여 중간체 B-1- 1을 17.2 g 얻었다. 1 equivalent of magnesium bromide solution (0.5M tetrahydrofuran) is added dropwise at 0 ° C. and slowly cooled to room temperature. After stirring for 1 hour at room temperature, the reaction solution is poured into 500 mL of ice water and the layers are separated. The organic layer is separated, treated with anhydrous magnesium sulfate and concentrated. The concentrated residue was recrystallized from tetrahydrofuran and methanol to obtain 17.2 g of intermediate B-1-1.
b) 화합물 B-1의 합성 b) Synthesis of Compound B-1
500 mL의 등근 바닥 플라스크에 상기 합성된 중간체 B-1-1 17.2g (56.9 mmol)을 테트라하이드로퓨란 200 mL, 증류수 100 mL를 넣고, 다이벤조퓨란 -3-보론산 (cas: 395087-89-5) 2 당량， 테트라키스트리페닐포스핀 팔라듐 0.03 당량, 탄산칼륨 2
당량을 넣고 질소 대기하에서 가열 환류한다. 18 시간 후 반웅액을 넁각시키고, 석출된 고체를 여과하고， 물 500 mL로 씻는다. 고체를 모노클로로벤젠 500 mL로 재결정하여 화합물 B-1을 12.87 g 얻었다. 200 mL of tetrahydrofuran and 100 mL of distilled water were added to a 500 mL equipotential bottom flask containing 17.2 g (56.9 mmol) of the above-described intermediate B-1-1, dibenzofuran-3-boronic acid (cas: 395087-89- 5) 2 equivalents, tetrakistriphenylphosphine palladium 0.03 equivalents, potassium carbonate 2 Add the equivalent and heat reflux under nitrogen atmosphere. After 18 hours the reaction solution was cooled down, the precipitated solid was filtered off and washed with 500 mL of water. The solid was recrystallized from 500 mL of monochlorobenzene to give 12.87 g of compound B-1.
LC/MS calculated for: C39H23N302 Exact Mass: 565.1790 found for: 566.18 [M+H] 합성예 2: 화합물 B-3의 합성 LC / MS calculated for: C39H23N302 Exact Mass: 565.1790 found for: 566.18 [M + H] Synthesis Example 2: Synthesis of Compound B-3
a) 중간체 B-3-1의 합성 a) Synthesis of Intermediate B-3-1
질소 환경에서 magnesium (그 86 g, 323 mmol)과 iodine(1.64 g, 6.46 mmol)을 tetrahydrofomn(THF) 0.1 L에 넣고 30분간 교반시킨 후, 여기에 THF 0.3 L에 녹아있는 ！^！ - ^- ^ ^？^쒜^ ！ 을 0 °C에서 30분에 걸쳐 천천히 적가한다. 이렇게 만들어진 흔합액을 THF 0.5 L에 녹아있는 시아누릭클로라이드 64.5 g (350 mmol) 용액에 0 °C에서 30분에 걸쳐 천천히 적가한다. 반응 완료 후 반응액에 물을 넣고 dichloromethane(DCM)로 추출한 다음 무수 MgS04로 수분을 제거한 후, 필터하고 감압 농축하였다. 이렇게 얻어진 잔사를 flash column chromatography로 분리 정제하여 중간체 B-3-l(79.4 g, 65 %)을 얻었다. b) 화합물 B-3의 합성 In a nitrogen environment, magnesium (86 g, 323 mmol) and iodine (1.64 g, 6.46 mmol) were added to 0.1 L of tetrahydrofomn (THF), stirred for 30 minutes, and dissolved in 0.3 L of THF.！ ^！-^- ^ ^？ ^ 쒜 ^！ Slowly add dropwise at 0 ° C over 30 minutes. The mixture thus prepared is slowly added dropwise to a solution of 64.5 g (350 mmol) of cyanuric chloride dissolved in 0.5 L of THF over 30 minutes at 0 ° C. After the reaction was completed, water was added to the reaction solution, and extracted with dichloromethane (DCM), and then water was removed with anhydrous MgS0 4 , filtered and concentrated under reduced pressure. The obtained residue was separated and purified through flash column chromatography to obtain Intermediate B-3-l (79.4 g, 65%). b) Synthesis of Compound B-3
증간체 B-3-1을 사용하여 상기 합성예 1의 b)와 같은 방법으로 화합물 B-3를 합성하였다. Compound B-3 was synthesized in the same manner as in b) of Synthesis Example 1 using Intermediate B-3-1.
LC/MS calculated for: C45H27N302 Exact Mass: 641.2103 found for 642.21 [M+H] 합성예 3: 화합물 B-17의 합성
LC / MS calculated for: C 45 H 27 N 302 Exact Mass: 641.2103 found for 642.21 [M + H] Synthesis Example 3: Synthesis of Compound B-17
a) 중간체 B-17-1의 합성 a) Synthesis of Intermediate B-17-1
500 mL의 등근 바닥 플라스크에 2,4-디클로로 -6-페닐트리아진 22.6g (100 mmol)을 테트라하이드로퓨란 100 mL, 를루엔 100 mL, 증류수 100 mL를 넣고， 다이벤조퓨란 -3-보론산 (CAS No.: 395087-89-5) 0.9 당량, 테트라키스트리페닐포스핀 팔라듐 0.03 당량， 탄산칼륨 2 당량을 넣고 질소 대기하에서 가열 환류한다. 6 시간 후 반웅액을 냉각시키고， 물층을 제거한 후， 유기층을 감압하에서 건조시킨다. 얻어진 고체를 물과 핵산으로 씻어준 후, 고체를 를루엔 200 mL로 재결정하여 중간체 B-17-1을 21.4 g(60% 수율) 얻었다. 22.6 g (100 mmol) of 2,4-dichloro-6-phenyltriazine was added to 100 mL of tetrahydrofuran, 100 mL of toluene and 100 mL of distilled water in a 500 mL back-bottomed flask, followed by dibenzofuran-3-boronic acid. (CAS No .: 395087-89-5) 0.9 equivalents, tetrakistriphenylphosphine palladium 0.03 equivalents, potassium carbonate 2 equivalents are added and heated to reflux under a nitrogen atmosphere. After 6 hours, the reaction mixture was cooled, the water layer was removed, and the organic layer was dried under reduced pressure. The obtained solid was washed with water and nucleic acid, and the solid was recrystallized with 200 mL of toluene to obtain 21.4 g (60% yield) of intermediate B-17-1.
b) 화합물 B-17의 합성 b) Synthesis of Compound B-17
500 mL의 둥근 바닥 플라스크에 상기 합성된 중간체 8-17-1 (56.9 1 ^1)을 테트라하이드로퓨란 200 mL, 증류수 100 mL를 넣고, 3,5-다이페닐벤젠보론산 (CAS No.: 128388-54-5) 1.1 당량, 테트라키스트리페닐포스핀 팔라듐 0.03 당량， 탄산칼륨 2 당량을 넣고 질소 대기하에서 가열 환류한다. 18 시간 후 반응액을 넁각시키고, 석출된 고체를 여과하고, 물 500 mL로 씻는다. 고체를 모노클로로벤젠 500 mL로 재결정하여 화합물 B-17을 얻었다. 200 mL of tetrahydrofuran and 100 mL of distilled water were added to a 500 mL round bottom flask with Intermediate 8-17-1 (56.9 1 ^ 1), and 3,5-diphenylbenzeneboronic acid (CAS No .: 128388 -54-5) Add 1.1 equivalents, tetrakistriphenylphosphine palladium 0.03 equivalents, potassium carbonate 2 equivalents and reflux under a nitrogen atmosphere. After 18 hours, the reaction solution was cooled, the precipitated solid was filtered and washed with 500 mL of water. The solid was recrystallized with 500 mL of monochlorobenzene to give compound B-17.
LC/MS calculated for: C39H25N30 Exact Mass: 555.1998 found for 556.21 [M+H] 합성예 4: 화합물 B-124의 합성 LC / MS calculated for: C39H25N30 Exact Mass: 555.1998 found for 556.21 [M + H] Synthesis Example 4: Synthesis of Compound B-124
a) 중간체 B-124-1의 합성
1-브로모 -3-클로로 -5-페닐벤젠과 비페닐 -4-보론산 1.1 당량을 사용하여 상기 합성예 1의 b)와 같은 방법으로 중간체 B-124-1을 합성하였다. 이때 재결정 대신 핵산을 이용한 플래쉬컬럼을 통해 생성물을 정제하였다. a) Synthesis of Intermediate B-124-1 Intermediate B-124-1 was synthesized in the same manner as b) of Synthesis Example 1 using 1-bromo-3-chloro-5-phenylbenzene and 1.1 equivalents of biphenyl-4-boronic acid. At this time, the product was purified by flash column using nucleic acid instead of recrystallization.
b) 중간체 B-124-2의 합성 b) Synthesis of Intermediate B-124-2
500 mL등근 바닥 플라스크에 상기 합성된 중간체 B-124-1 30 g (88.02 mmol)을 In a 500 mL back-bottom flask, 30 g (88.02 mmol) of the intermediate B-124-1 synthesized above were added.
DMF 250 mL에 넣고, 다이클로로다이페닐포스피노페로센 팔라듐 0.05 당량， In 250 mL of DMF, 0.05 equivalent of dichlorodiphenylphosphinoferrocene palladium,
비스피나콜라도 다이보론 1.2 당량, 초산칼륨 2 당량을 넣고 질소 대기하에서 18 시간 동안 가열 환류시켰다. 반웅액을 넁각시키고, 물 1 L에 적하시켜 고체를 잡는다. 얻어진 고체를 끓는 를루엔에 녹여 활성탄소를 처리 후 실리카겔에서 여과한 후 여액을 농축한다. 농축된 고체를 소량의 핵산과 교반 후， 고체를 여과하여 중간체 Bispinacola was also added with 1.2 equivalents of diborone and 2 equivalents of potassium acetate and heated to reflux for 18 hours under a nitrogen atmosphere. The reaction solution is allowed to stand and dipped in 1 L of water to obtain a solid. The obtained solid is dissolved in boiling toluene, treated with activated carbon, filtered through silica gel, and the filtrate is concentrated. After stirring the concentrated solid with a small amount of nucleic acid, the solid was filtered
B-124-2를 28.5 g(70% 수율) 얻었다. 28.5 g (70% yield) of B-124-2 was obtained.
c) 화합물 B-124의 합성 c) Synthesis of Compound B-124
중간체 B-124-2와 중간체 B-17-1을 각각 1.0 당량씩 사용하여 상기 합성예 3의 b)와 같은 방법으로 화합물 B-124를 합성하였다. Compound B-124 was synthesized in the same manner as in b) of Synthesis Example 3 using 1.0 equivalent of Intermediate B-124-2 and Intermediate B-17-1, respectively.
LC/MS calculated for: C45H29N30 Exact Mass: 627.2311 found for 628.22 [M+H] 합성예 5: 화합물 B-23의 합성 LC / MS calculated for: C 45 H 29 N 30 Exact Mass: 627.2311 found for 628.22 [M + H] Synthesis Example 5: Synthesis of Compound B-23
500 mL등근바닥플라스크에 시아누릭클로라이드 15 g(8 L34 mmol)을 무수 테트라하이드로퓨란 200 mL에 녹이고, 질소대기하에서 4-바이페닐 15 g (8 L34 mmol) of cyanuric chloride was dissolved in 200 mL of anhydrous tetrahydrofuran in a 500 mL back bottom flask, and 4-biphenyl was removed under nitrogen atmosphere.
마그네슴브로마이드 용액 (0.5M 테트라하이드로퓨란 ) 1 당량을 0 °C에서 적가하고 서서히 상온으로 을린다. 상온에서 1 시간 동안 교반한 후, 반응액을 얼음물 500 mL에 넣고 층분리시킨다. 유기층을 분리하고 무수 황산마그네슴을 처리하고 1 equivalent of magnesium bromide solution (0.5M tetrahydrofuran) is added dropwise at 0 ° C. and slowly cooled to room temperature. After stirring for 1 hour at room temperature, the reaction solution was poured into 500 mL of ice water and the layers were separated. Isolate the organic layer and treat anhydrous magnesium sulfate
농축한다. 농축된 잔사를 테트라하이드로퓨란과 메탄올로 재결정하여 중간체 B-23- 1을 17.2 g 얻었다ᅳ
b) 중간체 B-23-2의 합성 Concentrate. The concentrated residue was recrystallized from tetrahydrofuran and methanol to obtain 17.2 g of intermediate B-23-1. b) synthesis of intermediate B-23-2
중간체 B-23-1을 사용하여 상기 합성예 3의 a)와 같은 방법을 사용하여 중간체 B-23-2을 합성하였다. Intermediate B-23-2 was synthesized using the same method as in a) of Synthesis Example 3 using Intermediate B-23-1.
c) 화합물 B-23의 합성 c) Synthesis of Compound B-23
중간체 B-23-2와 1.1 당량의 3,5-다이페닐벤젠보론산을 사용하여 상기 합성예 Synthesis Example Using Intermediate B-23-2 and 1.1 Equivalent of 3,5-Diphenylbenzeneboronic Acid
3의 b)와 같은 방법으로 화합물 B-23을 합성하였다. Compound B-23 was synthesized in the same manner as b).
LC/MS calculated for: C45H29N30 Exact Mass: 627.231 1 found for 628.24 [M+H] 합성예 6: 화합물 B-24의 합성 LC / MS calculated for: C 45 H 29 N 30 Exact Mass: 627.231 1 found for 628.24 [M + H] Synthesis Example 6 Synthesis of Compound B-24
[반응식 6] Scheme 6
중간체 B-23-2와 1.1 당량의 B-[U':4',r-Terphenyl]-3-yI boiOnic acid을 사용하여 상기 합성예 3의 b)와 같은 방법으로 화합물 B-24를 합성하였다. Compound B-24 was synthesized by the same method as b) of Synthesis Example 3, using Intermediate B-23-2 and 1.1 equivalents of B- [U ': 4', r-Terphenyl] -3-yI boiOnic acid. .
LC/MS calculated for: C45H29N30 Exact Mass: 627.231 1 found for 628.24 [M+H] 합성예 7: 화합물 B-20의 합성 LC / MS calculated for: C 45 H 29 N 30 Exact Mass: 627.231 1 found for 628.24 [M + H] Synthesis Example 7 Synthesis of Compound B-20
중간체 B-17-1와 1.1 당량의 (5'-phenyl[ 1 , 1 ':3', l"-terphenyl]-4-yl)-boronic acid(CAS No.: 491612-72-7)을 사용하여 상기 합성예 3의 b)와 같은 방법으로 화합물 B-20을
합성하였다. Intermediate B-17-1 and 1.1 equivalents of (5'-phenyl [1, 1 ': 3', l "-terphenyl] -4-yl) -boronic acid (CAS No .: 491612-72-7) were used Compound B-20 in the same manner as in Synthesis Example b) Synthesized.
LC/MS calculated for: C45H29N30 Exact Mass: 627.2311 found for 628.24 [M+H] 합성예 8: 화합물 B-기의 합성 LC / MS calculated for: C 45 H 29 N 30 Exact Mass: 627.2311 found for 628.24 [M + H] Synthesis Example 8: Synthesis of Compound B-Group
a) 중간체 B-71-1의 합성 a) Synthesis of Intermediate B-71-1
500 mL의 등근 바닥 플라스크에 3-브로모 -디벤조퓨란 14.06g (56.90mmol), 테트라하이드로퓨란 200 mL, 증류수 lOO mL를 넣고, 3'-클로로 -페닐보론산 1 당량, 테트라키스트리페닐포스핀 팔라듐 0.03 당량, 탄산칼륨 2 당량을 넣고 질소 대기하에서 가열 환류한다. 18 시간 후 반응액을 냉각시키고, 석출된 고체를 여과하고, 물 500 mL로 씻는다. 고체를 모노클로로벤젠 500 mL로 재결정하여 중간체 B-71-1을 12.05 g 얻었다. (수율 76%) b) 중간체 B-71-2의 합성 Into a 500 mL back-bottom flask, 14.06 g (56.90 mmol) of 3-bromo-dibenzofuran, 200 mL of tetrahydrofuran, 100 mL of distilled water, 1 equivalent of 3'-chloro-phenylboronic acid, tetrakistriphenylphosphate 0.03 equivalents of pin palladium and 2 equivalents of potassium carbonate are added and heated to reflux under a nitrogen atmosphere. After 18 hours, the reaction solution is cooled, and the precipitated solid is filtered and washed with 500 mL of water. The solid was recrystallized from 500 mL of monochlorobenzene to give 12.05 g of intermediate B-71-1. (Yield 76%) b) Synthesis of Intermediate B-71-2
500 mL등근 바닥 플라스크에 상기 합성된 중간체 B-71—1 24.53 g (88.02 mmol)을 디엠에프 250 mL에 넣고, 다이클로로다이페닐포스피노페로센 팔라듐 0.05 당량, 비스피나콜라도 다이보론 1.2 당량， 초산칼륨 2 당량을 넣고 질소 대기하에서 18 시간 동안 가열 환류시켰다. 반응액을 냉각시키고， 물 1 L에 적하시켜 고체를 잡는다. 얻어진 고체를 끓는 를루엔에 녹여 활성탄소를 처리 후 실리카겔에서 여과한 후 여액을 농축한다. 농축된 고체를 소량의 핵산과 교반 후， 고체를 여과하여 중간체 B-71-2를 22.81g 얻었다. (수율 70%) c) 화합물 B-기의 합성 In a 500 mL back-bottom flask, 24.53 g (88.02 mmol) of the intermediate B-71—1 synthesized above was placed in 250 mL of DMMP, 0.05 equivalent of dichlorodiphenylphosphinoferrocene palladium, 1.2 equivalent of bispinola colorado diboron, potassium acetate 2 equivalents was added and heated to reflux for 18 hours under a nitrogen atmosphere. The reaction solution is cooled and added dropwise to 1 L of water to obtain a solid. The obtained solid is dissolved in boiling toluene, treated with activated carbon, filtered through silica gel, and the filtrate is concentrated. After stirring the concentrated solid with a small amount of nucleic acid, the solid was filtered to obtain 22.81 g of intermediate B-71-2. (Yield 70%) c) Synthesis of Compound B-Group
상기 합성한 중간체 B-71-2와 2,4-Bis([l ,l'-biphenyl]-4-yl)-6-chloro-l,3,5-
triazine을 각각 1.0 당량씩 사용하여 상기 합성예 a)와 같은 방법으로 화합물 B- 을 합성하였다. The synthetic intermediate B-71-2 and 2, 4 -Bis ([l, l'-biphenyl] - 4 -yl) -6-chloro-l, 3,5- Compounds B- were synthesized in the same manner as in Synthesis Example a) using 1.0 equivalent of triazine each.
LC/MS calculated for: C45H29N30 Exact Mass: 627.2311 found for 628.25 [M+H] 합성예 9: 화합물 B-129의 합성 LC / MS calculated for: C 45 H 29 N 30 Exact Mass: 627.2311 found for 628.25 [M + H] Synthesis Example 9: Synthesis of Compound B-129
[반웅식 9] [Banungsik 9]
l-Bromo-4-chloro-benzene과 2-naphthalene boronic acid를 각각 1.0 당량씩 사용하여 상기 합성예 8의 a)와 같은 방법으로 중간체 B-129-1을 합성하였다. Intermediate B-129-1 was synthesized in the same manner as in a) of Synthesis Example 8 using 1.0 equivalent of l-Bromo-4-chloro-benzene and 2-naphthalene boronic acid, respectively.
b) 중간체 B-129-2의 합성 b) Synthesis of Intermediate B-129-2
중간체 B-129-1와 비스피나콜라도 다이보론 1 : 1.2 당량비를 사용하여 상기 합성예 8의 b)와 같은 방법으로 중간체 B-129-2을 합성하였다 Intermediate B-129-1 and bispinacola were synthesized in the same manner as in b) of Synthesis Example 8 using the diborone 1: 1.2 equivalent ratio.
c) 화합물 B-129의 합성 c) Synthesis of Compound B-129
중간체 B-135-2와 B-17-1을 각각 1.0 당량씩 사용하여 상기 합성예 1의 b)와 같은 방법으로 화합물 B-129를 합성하였다. Compound B-129 was synthesized in the same manner as in b) of Synthesis Example 1 using 1.0 equivalent of Intermediate B-135-2 and B-17-1, respectively.
LC/MS calculated for: C37H23N30 Exact Mass: 525.18 found for 525.22 [M+H] LC / MS calculated for: C37 H23 N30 Exact Mass: 525.18 found for 525.22 [M + H]
(제 2 호스트의 제조) (Production of Second Host)
합성예 10: 화합물 HC-28의 합성
Synthesis Example 10 Synthesis of Compound HC-28
HC-28-3 HC-28-3
a) 중간체 HC-28-1의 합성 a) Synthesis of Intermediate HC-28-1
500mL플라스크에 중간체 A (30g, 121.9mmol), 4,4,4',4', 5,5,5',5'-옥타메틸 -2，2'- 바이 (1,3,2-다이옥사보로란) 1당량, 아세트산칼륨 2당량 및 1,1'-비스 (다이페닐포스피노) 페로센-팔라듐 ( Π )다이클로라이드 0.03 당량, 트리사이클로핵실포스핀 0.2당량을 Ν,Ν- 다이메틸포름아마이드 300mL에 넣은 후, 130 °C에서 12시간 교반하였다. 반응 완료 후, 반응 용액을 물과 EA로 추출하여 수득한 유기층으로부터 황산마그네슘을 사용하여 수분을 제거하고 농축하여， 컬럼 크로마토그래피로 정제하여 중간체 HC- 28-1을 흰색의 고체 (29.66g, 83%의 수율)로 얻었다. b) 중간체 HC-28-2의 합성 Intermediate A (30 g, 121.9 mmol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2'-bi (1,3,2-dioxabo in 500 mL flask 1 equivalent of Loran), 2 equivalents of potassium acetate and 0.03 equivalents of 1,1'-bis (diphenylphosphino) ferrocene-palladium (Π) dichloride, and 0.2 equivalents of tricyclonucleosilphosphine to Ν, Ν-dimethylformamide After putting into 300mL, the mixture was stirred at 130 ° C for 12 hours. After completion of the reaction, the reaction solution was extracted with water and EA to remove moisture using magnesium sulfate, concentrated and purified by column chromatography to give the intermediate HC-28-1 as a white solid (29.66 g, 83 Yield). b) synthesis of intermediate HC-28-2
500mL플라스크에 중간체 HC-28-1 29.66g (0.4 mol), 중간체 B (1-브로모 -2- 니트로 벤젠) 2당량, 탄산칼륨 2당량, 테트라키스 (트리페닐포스핀) 팔라듐 (0) ' 0.02당량을 1,4-다이옥산 200mL, 물 lOOmL 에 넣어준 후， 질소 기류 하에서 16시간 '동안 90°C로 가열하였다. 반웅 용매를 제거한후, 디클로로메탄에 녹여 500mL intermediate HC-28-1 in a flask 29.66g (0.4 mol), intermediate B (1- Bromo-2-nitro-benzene), 2 equivalents of potassium carbonate 2eq, tetrakis (triphenylphosphine) palladium (0), after 0.02 equivalents gave put in 200mL 1,4-dioxane, water lOOmL, it was heated to 90 ° C for 16 hours, was conducted in a nitrogen atmosphere. After removing the reaction solvent, dissolved in dichloromethane
실리카겔 /셀라이트로 여과하고, 유기 용매를 적당량 제거한 후, 메탄올로 재결정하여 중간체 HC-28-2를 고체 (16.92g, 58%의 수율)로 얻었다. c) 중간체 HC-28-3의 합성 Filtration with silica gel / celite followed by removal of an appropriate amount of an organic solvent and recrystallization with methanol yielded intermediate HC-28-2 as a solid (16.92 g, 58% yield). c) synthesis of intermediate HC-28-3
500 mL플라스크에 상기 합성한 중간체 HC-28-2 8.7g (30.2 mmol), 중간체 C(2- 브로모나프탈렌) 7.5g (36.2 mmol), 소듐 t-부록사이드 (NaOtBu) 4.3 g (45.3 mmol), Pd(dba)2 1.0 g (1.8 mmol), 트리 t-부틸포스핀 (P(tBu)3) 2.2 g (50% in 를루엔)를 자일렌 150 mL 에 넣고 질소 기류 하에서 12시간 동안 가열하여 환류하였다. 자일렌을 제거한 후, 이로부터 수득한 흔합물에 메탄올 200 mL를 가하여 결정화된 고형분을 여과한 후, 디클로로메탄에 녹여 실리카겔 /셀라이트로 여과하고， 유기 용매를 적당량 제거한 후, 아세톤으로 재결정하여 중간체 HC-28-3(9.83g, 77%의 수율)을 수득하였다.
d) 중간체 HC-28-4의 합성 In a 500 mL flask, 8.7 g (30.2 mmol) of the above-produced intermediate HC-28-2, 7.5 g (36.2 mmol) of intermediate C (2-bromonaphthalene) and 4.3 g (45.3 mmol) of sodium t-boxide (NaOtBu) 1.0 g (1.8 mmol) of Pd (dba) 2 and 2.2 g (50% in toluene) of trit-butylphosphine (P (tBu) 3 ) were added to 150 mL of xylene and heated under nitrogen stream for 12 hours. It was refluxed. After removing the xylene, 200 mL of methanol was added to the mixture obtained, and the crystallized solid was filtered. The mixture was dissolved in dichloromethane, filtered through silica gel / celite, an appropriate amount of the organic solvent was removed, and then recrystallized from acetone to give an intermediate. HC-28-3 (9.83 g, 77% yield) was obtained. d) synthesis of intermediate HC-28-4
1000ml 플라스크에 상기 합성한 중간체 HC-28-3 (211.37 g, 0.51 mol) 및 트리에틸 포스파이트 (528ml, 3.08mol)을 넣고 질소치환을 하고 12시간 동안 160°C에서 교반하였다. 반웅 종료 후, MeOH 3L를 넣고 교반 후, 필터하고, 여액을 휘발하였다. 컬럼 크로마토그래피로 정제 (Hexane) 하여 중간체 HC-28-4 (l52.14g, 78%의 수율)를 얻었다. e) 화합물 HC-28의 합성 Intermediate HC-28-3 (211.37 g, 0.51 mol) and triethyl phosphite (528ml, 3.08mol) were added to a 1000ml flask, and nitrogen-substituted and stirred at 160 ° C for 12 hours. After the completion of reaction, MeOH 3L was added thereto, stirred, and filtered. The filtrate was evaporated. Purification by column chromatography (Hexane) afforded the intermediate HC-28-4 (l 5 2.14 g, 78% yield). e) synthesis of compound HC-28
HC-28-4 HC-30-B HC-28-4 HC-30-B
합성예 10의 e)와 동일한 방법으로, 중간체 HC-28-B 대신 중간체 HC-30-B를 사용하여 화합물 HC-30을 합성하였다. 합성예 12: 화합물 HC-29의 합성
In the same manner as in e) of Synthesis Example 10, Compound HC-30 was synthesized using Intermediate HC-30-B instead of Intermediate HC-28-B. Synthesis Example 12 Synthesis of Compound HC-29
HC-28-4 HC-29-B HC-29 HC-28-4 HC-29-B HC-29
합성예 10의 e)와 동일한 방법으로, 중간체 HC-28-B 대신 중간체 HC-29-B 사용하여 화합물 HC-29를 합성하였다. 합성예 13: 화합물 HC-18의 합성 In the same manner as in e) of Synthesis Example 10, Compound HC-29 was synthesized using Intermediate HC-29-B instead of Intermediate HC-28-B. Synthesis Example 13: Synthesis of Compound HC-18
14] 14]
합성예 10의 c)와 동일한 방법으로, 2-브로모나프탈렌 대신 4-브로모비페닐 중간체를 이용하여 중간체 HC-18-1을 합성하였다. b) 중간체 HC-18-2의 합성 In the same manner as in c) of Synthesis Example 10, intermediate HC-18-1 was synthesized using 4-bromobiphenyl intermediate instead of 2-bromonaphthalene. b) synthesis of intermediate HC-18-2
합성예 10의 d)와 동일한 방법으로， 중간체 HC-18-2를 합성하 c) 중간체 HC-18-3의 합성 Synthesis of Intermediate HC-18-2 in the same manner as in d) of Synthesis Example 10 c) Synthesis of Intermediate HC-18-3
[반웅식 15]
[Banungsik 15]
HC-18-3
중간체 HC-18-A, HC-18-B를 이용하여 합성예 1의 b)와 동일한 방법으로 중간체 HC-18-3을 합성하였다. d) 화합물 HC-18의 합성 HC-18-3 Intermediate HC-18-3 was synthesized using the intermediate HC-18-A and HC-18-B in the same manner as in b) of Synthesis Example 1. d) Synthesis of Compound HC-18
16] 16]
합성예 10의 e)와 동일한 방법으로, 상기 합성한 중간체 HC-18-2 및 HC-18- 3을 이용하여 화합물 HC-18을 합성하였다. 고합성예 1: 화합물 Ref.l의 합성 In the same manner as in e) of Synthesis Example 10, Compound HC-18 was synthesized using the synthesized intermediate HC-18-2 and HC-18-3. High Synthesis Example 1 Synthesis of Compound Ref.l
1-1 Ref.1 1-1 Ref.1
등근바닥 플라스크에 중간체 1-1 8g(31.2mmol), 4-아이오도바이페닐 Intermediate 1-1 8g (31.2mmol), 4-iodobiphenyl
20.5g(73.32mmol), Cul 1.19g(6.24mmol), 1,10-phenanthoroline 1.12g(6.24mmol), K2C03 12.9g(93.6mmol)을 넣고 DMF 50ml을 가하여 질소 분위기 하에서 24시간 동안 환류 교반 시킨다. 반응 종료 후 증류수로 가하여 결정을 석출시키고， 여과하였다. 고체 xylene 250ml에 녹여 실리카 겔로 여과한 후, 백색 고체로 석출시켜 참고화합물인 Ref.l 16.2g (수율 93%)을 수득하였다. Add 20.5 g (73.32 mmol), Cul 1.19 g (6.24 mmol), 1,10-phenanthoroline 1.12 g (6.24 mmol), K 2 C0 3 12.9 g (93.6 mmol), and add 50 ml of DMF to reflux for 24 hours under nitrogen atmosphere. Stir. After the reaction was completed, distilled water was added to precipitate crystals and filtered. It was dissolved in 250 ml of solid xylene, filtered through silica gel, and precipitated as a white solid to obtain 16.2 g of Ref.l (yield 93%) as a reference compound.
(유기 발광소자의 제작) (Production of Organic Light Emitting Device)
실시예 1 Example 1
ΠΌ (Indium tin oxide)가 1500 A 두께로 박막 코팅된 유리 기판올 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올
등의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 이송 시킨 다음 산소 플라즈마를 이용하여 상기 기판을 10분간 세정 한 후 진공 증착기로 기판을 이송하였다. 이렇게 준비된 ΠΌ 투명 전극을 양극으로 사용하여 ITO 기판 상부에 화합물 A을 진공 증착하여 700A 두께의 정공 주입층을 형성하고 상기 주입층 상부에 화합물 B를 50A의 두께로 증착한 후， 화합물 C를 700A의 두께로 증착하여 정공수송층을 형성하였다. 상기 정공수송층 상부에 화합물 C-1을 400A의 두께로 증착하여 정공수송보조층을 형성하였다. 정공수송보조층 상부에 화합물 B-24 및 화합물 HC-28을 동시에 호스트로사용하고 도판트로 [Ir(piq)2acac] 2wt% 로 도큉하여 진공 증착으로 400A 두께의 발광층을 형성하였다. 여기서 화합물 B-24와 화합물 HC-28은 3:7 중량비로 사용되었다. 이어서 상기 발광층 상부에 화합물 D와 Liq를 동시에 1 :1 비율로 진공 증착하여 300 A 두께의 전자수송층을 형성하고 상기 전자수송층 상부에 Liq l5A과 A1 1200A을 순차적으로 진공 증착 하여 음극을 형성함으로써 유기발광소자를 제작하였다. Indium tin oxide was thin film-coated glass substrate with a thickness of 1500 A and washed with distilled water ultrasonically. After distilled water wash, isopropyl alcohol, acetone, methanol Ultrasonic cleaning with a solvent, and the like was dried and then transferred to a plasma cleaner, and then the substrate was cleaned for 10 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator. Compound A was vacuum deposited on the ITO substrate to form a hole injection layer having a thickness of 700 A using the prepared ΠΌ transparent electrode as an anode, and then compound C was deposited to a thickness of 50 A on the injection layer. Deposition to a thickness to form a hole transport layer. Compound C-1 was deposited to a thickness of 400 A on the hole transport layer to form a hole transport auxiliary layer. Compound B-24 and Compound HC-28 were simultaneously used as a host on the hole transport auxiliary layer, and the light emitting layer having a thickness of 400A was formed by vacuum evaporation with 2 wt% of [Ir (piq) 2 acac]. Here compound B-24 and compound HC-28 were used in a 3: 7 weight ratio. Subsequently, the compound D and Liq are simultaneously vacuum deposited on the light emitting layer at a ratio of 1: 1 to form an electron transport layer having a thickness of 300 A, and the Liq l5A and A1 1200A are sequentially vacuum deposited on the electron transport layer to form a cathode. The device was produced.
상기 유기발광소자는 5층의 유기 박막층을 가지는 구조로 되어 있으며, 구체적으로 다음과 같다. The organic light emitting device has a structure having five organic thin film layers, specifically as follows.
ΠΌ/화합물 A(700A)/화합물 Β(50Α)/화합물 C(700A)/화합물 C-l(400 ΠΌ / Compound A (700A) / Compound Β (50Α) / Compound C (700A) / Compound C-1 (400
A)/EML [화합물 B-24： 화합물 HC-28： [Ir(piq)2acac] (2wt%)] (400 A) / 화합물 D： A) / EML [Compound B-24: Compound HC-28: [Ir (piq) 2 acac] (2 wt%)] (400 A) / Compound D:
Liq(300A) / Liq(l5A) / A1(1200A)의 구조로 제작하였다. It was produced in the structure of Liq ( 3 00A) / Liq (l 5 A) / A1 (1 2 00A).
화합물 A: N4,N4'-diphenyl-N4,N4'-bis(9-phenyl-9H-carbazol-3-yl)biphenyl^^ diamine Compound A: N4, N4'-diphenyl-N 4 , N4'-bis (9-phenyl-9H-carbazol-3-yl) biphenyl ^^ diamine
화합물 B: 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN), Compound B: 1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN),
화합물 C: N— (biphenyl-4-yl)-9,9-dimethyl-N-(4-(9-phenyl-9H-carbazol-3-yD^ Compound C: N— (biphenyl-4-yl) -9,9-dimethyl-N- (4- (9-phenyl-9H-carbazol-3-yD ^
9H-fluoren-2-amine 9H-fluoren-2-amine
화합물 C-1 : N,N-di([ 1 , 1 '-biphenyl]-4-yl)-7,7-dimethyl-7H-fluoreno[4,3-b]benzofuran- 10- amine Compound C-1: N, N-di ([1, 1 '-biphenyl] -4-yl) -7,7-dimethyl-7H-fluoreno [4,3-b] benzofuran-10-amine
화합물 D: 8-(4-(4,6-di(naphthalen-2-yl)-l,3,5-triazin-2-yl)phenyl)quinoline 실시예 2내지 9,및 참고예 1 내지 3 Compound D: 8- (4- (4,6-di (naphthalen-2-yl) -1,3,5-triazin-2-yl) phenyl) quinoline Examples 2 to 9, and Reference Examples 1 to 3
하기 표 1에 기재된 바와 같이 제 1 호스트 및 제 2 호스트를 사용하여 실시예 1 과 동일한 방법으로 유기 발광 소자를 제작하였다.
평가 As shown in Table 1 below, an organic light emitting device was manufactured in the same manner as in Example 1, using the first host and the second host. evaluation
상기 실시예 1 내지 9， 및 참고예 1 내지 3에 따른 유기 발광 소자의 수명 특성을 하기 방법으로 평가하여 그 결과를 표 1에 나타내었다. The lifespan characteristics of the organic light emitting diodes according to Examples 1 to 9 and Reference Examples 1 to 3 were evaluated by the following methods, and the results are shown in Table 1 below.
수명 측정 Life measurement
제조된 유기 발광 소자에 대해 폴라로닉스 수명측정 시스템을 사용하여 실시예 1 내지 9 및 참고예 1 내지 3의 소자를 초기휘도 (cd/m2)를 9000cd/m2로 발광시키고 시간 경과에 따른 휘도의 감소를 측정하여 초기 휘도 대비 97%로 휘도가 감소된 시점을 T97 수명으로 측정하였다. 참고예 1의 수명을 100%로 하여 상대비율로 표기하였다. Performed using polar Optronics lifetime measuring system for the manufacture of organic light emitting device in Example 1 to 9 and Reference Examples 1 to 3, the initial luminance of the device of (cd / m 2) the brightness of the light emission and time in 9000cd / m 2 The decrease in luminance was measured by the T97 life time when the luminance was reduced to 97% of the initial luminance. The lifetime of Reference Example 1 was expressed as a relative ratio with 100%.
【표 1】 Table 1
Claims
[화학식 1] [화학식 2] [화학식 3 [Formula 1] [Formula 2] [Formula 3
상기 화학식 1에서, In Chemical Formula 1,
X1는 0 또는 S이고， X 1 is 0 or S,
Z1 내지 Z3은 각각 독립적으로 N 또는 CRa이고, Z 1 to Z 3 are each independently N or CR a ,
Z1 내지 Z3 중 적어도 둘은 N이고, At least two of Z 1 to Z 3 are N,
L1 내지 L3은 각각 독립적으로 단일결합, 또는 치환 또는 비치환된 C6 내지 C20 아릴렌기이고, L 1 to L 3 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,
A1 및 A2는 각각 독립적으로 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C2 내지 C30 헤테로고리기이고, A 1 and A 2 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
A1 및 A2 중 적어도 하나는 치환 또는 비치환된 C6 내지 C30 아릴기이고，At least one of A 1 and A 2 is a substituted or unsubstituted C6 to C30 aryl group,
Ra 및 R1 내지 R3은 각각 독립적으로 수소, 중수소, 시아노기, 치환 또는 비치환된 C1 내지 C10 알킬기, 또는 치환 또는 비치환된 C6 내지 C20 아릴기이며; R a and R 1 to R 3 are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C20 aryl group;
. 상기 화학식 2 및 3에서， . In Chemical Formulas 2 and 3,
Ar2는 치환 또는 비치환된 C6 내지 C20 아릴기이고, Ar 2 is a substituted or unsubstituted C6 to C20 aryl group,
화학식 2의 인접한 2개의 *은 화학식 3과 연결되고，
화학식 3과 연결되지 않은 화학식 2의 *은 각각 독립적으로 C-La-Rb이고, ΙΛ Υ1 및 Y2는 각각 독립적으로 단일결합, 또는 치환 또는 비치환된 C6 내只ᅳ C20 아릴렌기이고， Two adjacent * of Formula 2 are linked to Formula 3, * Of Formula 2, which is not linked to Formula 3, is each independently CL a -R b , and ΙΛ Υ 1 and Y 2 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,
Rb 및 R6 내지 R12는 각각 독립적으로 수소, 중수소, 시아노기, 치환 또는 비치환된 C1 내지 C10 알킬기, 또는 치환 또는 비치환된 C6 내지 C20 아릴기이다. R b and R 6 to R 12 are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C20 aryl group.
[청구항 2】 [Claim 2]
거 11항에 있어서, According to claim 11,
상기 제 1 호스트는 하기 화학식 1- 1으로 표현되는 유기 광전자 소자: The first host is an organic optoelectronic device represented by Formula 1-1:
화학식 1- 1 ] Formula 1-1]
상기 화학식 1- 1에서, In Chemical Formula 1-1,
X1는 O 또는 S이고, X 1 is O or S,
Z1 내지 Z3은 각각 독립적으로 N 또는 CRa이고, Z 1 to Z 3 are each independently N or CR a ,
Z1 내지 Z3 중 적어도 둘은 N이고, At least two of Z 1 to Z 3 are N,
L1 내지 L3은 각각 독립적으로 단일결합, 또는 치환 또는 비치환된 C6 내지 C20 아릴렌기이고, L 1 to L 3 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,
A2는 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C2 내지 C30 헤테로고리기이고, A 2 is a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
Ra 및 R1 내지 R5는 각각 독립적으로 수소, 중수소, 시아노기, 치환 또는 비치환된 C1 내지 C10 알킬기, 또는 치환 또는 비치환된 C6 내지 C20 아릴기이다. R a and R 1 to R 5 are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C20 aryl group.
[청구항 3】 [Claim 3]
제 1항에 있어서, The method of claim 1,
상기 거ᅵ1 호스트는 하기 화학식 1- 1 B-1 내지 화학식 1- 1 B-3 증 어느 하나로 표현되는 유기 광전자 소자:
[화학식 1- l B-l] [ 1- 1 B-2] Wherein the host 1 is an organic optoelectronic device represented by one of the following Chemical Formulas 1-1 B-1 to 1-1 B-3: [Formula 1-l Bl] [1-1 B-2]
[화학식 1- 1 B-3] [Formula 1-1 B-3]
상기 화학식 1- 1 B-1 내지 1- I B-3에서， In Chemical Formulas 1-1 B-1 to 1-I B-3,
Ar1은 치환 또는 비치환된 C6 내지 C20 아릴기이고, Ar 1 is a substituted or unsubstituted C6 to C20 aryl group,
X1 및 X2는 각각 독립적으로 O 또는 S이고, X 1 and X 2 are each independently O or S,
Z1 내지 Z6은 각각 독립적으로 N 또는 CRa이고, Z 1 to Z 6 are each independently N or CR a ,
Z1 내지 Z3 중 적어도 둘은 N이고, At least two of Z 1 to Z 3 are N,
Z4 내지 Z6 중 적어도 둘은 N이고， At least two of Z 4 to Z 6 are N,
L1 내지 L3은 각각 독립적으로 단일결합， 또는 치환 또는 비치환된 C6 내지 C20 아릴렌기이고, L 1 to L 3 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,
Ra, Rc, Rd, Re 및 R1 내지 R5는 각각 독립적으로 수소， 중수소， 시아노기, 치환 또는 비치환된 C1 내지 C10 알킬기, 또는 치환 또는 비치환된 C6 내지 C20 아릴기이다. R a , R c , R d , R e and R 1 to R 5 are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C20 aryl group .
【청구항 4】 [Claim 4]
제 1항에 있어서, The method of claim 1,
상기 화학식 1의 A1은 치환 또는 비치환된 C6 내지 C20 아릴기이고, 상기 화학식 1의 A2는 치환 또는 비치환된 페닐기, 치환 또는 비치환된 바이페닐기, 치환 또는 비치환된 나프틸기, 치환 또는 비치환된 터페닐기， 치환 또는 비치환된 쿼터페닐기, 치환 또는 비치환된 디벤조퓨란일기， 치환 또는 비치환된 디벤조티오펜일기， 치환 또는 비치환된 피리미디닐기, 또는 치환 또는 비치환된
트리아지닐기인 유기 광전자 소자. A 1 of Formula 1 is a substituted or unsubstituted C6 to C20 aryl group, A 2 of Formula 1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, substituted Or an unsubstituted terphenyl group, a substituted or unsubstituted quarterphenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted pyrimidinyl group, or a substituted or unsubstituted Done An organic optoelectronic device which is a triazinyl group.
【청구항 5] [Claim 5]
제 4항에 있어서, The method of claim 4, wherein
상기 화학식 1의 A1은 하기 그룹 I에 나열된 치환기에서 선택되고， 상기 화학식 1의 A2는 하기 그룹 Π에 나열된 치환기에서 선택되는 유기 광전자 소자:A 1 in Formula 1 is selected from the substituents listed in Group I, and A 2 in Formula 1 is selected from the substituents listed in Group Π:
그룹 I ] . Group I].
상기 그룹 I에서， *은 L2와의 연결 지점이고， In group I, * is a connection point with L 2 ,
상기 그룹 π에서， *은 L3와의 연결 지점이다. In the group π, * is the point of attachment to L 3 .
【청구항 6] [Claim 6]
제 1항에 있어서,
상기 제 2 호스트는 하기 화학식 2C로 표현되는 유기 광전자 소자:The method of claim 1, The second host is an organic optoelectronic device represented by Formula 2C:
화학식 2C] Formula 2C]
상기 화학식 2C에서, In Chemical Formula 2C,
Ar2는 치환 또는 비치환된 C6 내지 C20 아릴기이고, Ar 2 is a substituted or unsubstituted C6 to C20 aryl group,
Lal 및 L^ Y1 및 Y2는 각각 독립적으로 단일결합, 또는 치환 또는 비치환된 C6 내지 C20 아릴렌기이고, L al and L ^ Y 1 and Y 2 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,
Rbl, Rb2 및 R6 내지 R12는 각각 독립적으로 수소, 중수소， 시아노기, 치환 또는 비치환된 C1 내지 C10 알킬기, 또는 치환 또는 비치환된 C6 내지 C20 아릴기이다. R bl , R b2 and R 6 to R 12 are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C20 aryl group.
【청구항 7】 [Claim 7]
제 6항에 있어서, The method of claim 6,
상기 Ar2은 치환 또는 비치환된 페닐기 , 치환 또는 비치환된 바이페닐기 , 치환 또는 비치환된 나프틸기, 또는 치환 또는 비치환된 터페닐기인 유기 광전자 소자. Wherein Ar 2 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, or a substituted or unsubstituted terphenyl group.
【청구항 8】 [Claim 8]
거 11항에 있어서， According to claim 11,
상기 게 1 호스트는 하기 화학식 1- 1 B-1 또는 화학식 1- I B-2로 표현되고， 상기 게 2 호스트는 하기 화학식 2C-a로 표현되는 유기 광전자 소자: The Crab 1 host is represented by the following Chemical Formula 1-1 B-1 or Formula 1-I B-2, and the Crab 2 host is represented by the following Chemical Formula 2C-a:
1- 1 B-1] [화학식 1- 1 B-2] [화학식 2C-a] 1-1 B-1] [Formula 1-1 B-2] [Formula 2C-a]
상기 화학식 1- 1 B-1, 화학식 1- I B-2 및 화학식 2C-a에서
Ar1 및 Ar2는 각각 독립적으로, 치환 또는 비치환된 페닐기, 치환 또는 비치환된 바이페닐기, 치환 또는 비치환된 나프틸기, 치환 또는 비치환된 터페닐기, 또는 치환 또는 비치환된 쿼터페닐기이고, In Formula 1-1 B-1, Formula 1-I B-2, and Formula 2C-a Ar 1 and Ar 2 are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted quarterphenyl group. ,
X1 및 X2는 각각 독립적으로 O 또는 S이고, X 1 and X 2 are each independently O or S,
Z1 내지 Z3은 각각 독립적으로 N 또는 CRa이고, Z 1 to Z 3 are each independently N or CR a ,
Z1 내지 Z3 중 적어도 둘은 N이고, At least two of Z 1 to Z 3 are N,
L1 내지 L3, Lal, La2, Y1 및 Y2는 각각 독립적으로 단일결합, 또는 치환 또는 비치환된 C6 내지 C20 아릴렌기이고, L 1 to L 3 , L al , L a2 , Y 1 and Y 2 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,
Ra, Rbl, Rb2, R°, Rd, Re 및 R1 내지 R5는 각각 독립적으로 수소, 중수소， 시아노기, 치환 또는 비치환된 C1 내지 C10 알킬기， 또는 치환 또는 비치환된 C6 내지 C20 아릴기이다. R a , R bl , R b2 , R °, R d , R e and R 1 to R 5 are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C20 aryl group.
【청구항 9] [Claim 9]
제 1항에 있어서, The method of claim 1,
상기 최대 발광 파장이 550 nm 내지 750 nm인 인광 도편트는 이리듐 (Ir) 착체 또는 백금 (Pt) 착체인 유기 광전자 소자. The phosphorescent dopant having the maximum emission wavelength of 550 nm to 750 nm is an iridium (Ir) complex or a platinum (Pt) complex.
【청구항 10】 [Claim 10]
제 9항에 있어서, . The method of claim 9, wherein.
상기 백금 (Pt) 착체는 하기 화학식 4-1로 표현되는 유기 광전자 소자: The platinum (Pt) complex is an organic optoelectronic device represented by Formula 4-1:
[화학식 4-1 ] [Formula 4-1]
상기 화학식 4-1에서, In Chemical Formula 4-1,
X^, XB, Xc 및 ^는 각각 1A, IB, 1 C 및 ID와 불포화 고리를 형성하는 원소이고, 각각 독립적으로 C 또는 N이고, X ^, X B , X c and ^ are each an element forming an unsaturated ring with 1A, IB, 1 C and ID, each independently C or N,
1A, IB, 1 C 및 ID는 각각 독립적으로, 치환 또는 비치환된 C6 내지 C30
아릴기， 또는 치환 또는 비치환된 C2 내지 C30 헤테로고리기이고, 1A, IB, 1 C and ID are each independently substituted or unsubstituted C6 to C30 An aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
LA, LB, Lc, L°, QA, QB, Qc 및 는 각각 독립적으로， 단일 결합, O, S, 치환 또는 비치환된 C1 내지 C30 알킬렌기, 치환 또는 비치환된 C2 내지 C30 알케닐렌기, 치환 또는 비치환된 C6 내지 C30 아릴렌기， 또는 치환 또는 비치환된 C2 내지 C30 헤테로아릴렌기이고， L A , L B , L c , L °, Q A , Q B , Q c and are each independently a single bond, O, S, a substituted or unsubstituted C1 to C30 alkylene group, a substituted or unsubstituted C2 To C30 alkenylene group, substituted or unsubstituted C6 to C30 arylene group, or substituted or unsubstituted C2 to C30 heteroarylene group,
RA, RB, Rc 및 는 각각 독립적으로， 수소, 중수소， 시아노기, 할로겐기, 실란기, 포스핀기, 아민기, 치환 또는 비치환된 C1 내지 C30 알킬기， 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C2 내지 C30 R A , R B , R c and are each independently hydrogen, deuterium, cyano group, halogen group, silane group, phosphine group, amine group, substituted or unsubstituted C1 to C30 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30
헤테로아릴기이고, Heteroaryl group,
RA, RB, Rc 및 RD는 각각 독립적으로 존재하거나， 인접한 기끼리 서로 연결되어 고리를 형성하고, R A , R B , R c and R D are each independently present or adjacent groups are connected to each other to form a ring,
n은 0 내지 5의 정수 중 하나이며, n is one of integers from 0 to 5,
a, b, c 및 d는 각각 독립적으로 0 내지 3의 정수 중 하나이다. a, b, c and d are each independently one of an integer of 0-3.
【청구항 11】 [Claim 11]
게 9항에 있어서, The method of claim 9,
상기 이리듐 (Ir) 착체는 하기 화학식 4— 2로 표현되는 유기 광전자 소자: The iridium (Ir) complex is an organic optoelectronic device represented by the following formula 4-2:
-2] -2]
상기 화학식 4-2에서, In Chemical Formula 4-2,
2A, 2B 및 2C는 각각 독립적으로 치환 또는 비치환된 벤젠 고리이고， 2A, 2B 및 2C 중 적어도 하나는 인접한 착화합물과 융합 고리를 형성하고, R RF, RG, R", RJ및 RK는 각각 독립적으로， 수소, 중수소, 시아노기, 할로겐기, 실란기, 포스핀기， 아민기, 치환 또는 비치환된 C1 내지 C10 알킬기, 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C2 내지 C30 헤테로아릴기이고,
R£, RF, RG, RH, R1, RJ및 는 각각 독립적으로 존재하거나, 인접한 기끼리 서로 연결되어 고리를 형성하고, 2A, 2B and 2C are each independently a substituted or unsubstituted benzene ring, at least one of 2A, 2B and 2C forms a fused ring with an adjacent complex and RR F , R G , R ", R J and R K Are each independently hydrogen, deuterium, cyano group, halogen group, silane group, phosphine group, amine group, substituted or unsubstituted C1 to C10 alkyl group, substituted or unsubstituted C6 to C30 aryl group, or substituted or unsubstituted C2 to C30 heteroaryl group, R £ , R F , R G , R H , R 1 , R J and are each independently or adjacent groups are connected to each other to form a ring,
m은 1 내지 3의 정수 중 하나이다. m is one of the integers 1-3.
【청구항 12】 [Claim 12]
하기 화학식 1로 표현되는 제 1 호스트, 그리고 하기 화학식 2 및 화학식 3의 조합으로 표현되는 제 2 호스트를 포함하는 적색 인광 호스트용 조성물: A red phosphorescent host composition comprising a first host represented by Formula 1 and a second host represented by a combination of Formulas 2 and 3 below:
1] [화학식 2] [화학식 3] 1] [Formula 2] [Formula 3]
상기 화학식 1에서, In Chemical Formula 1,
X1는 O 또는 S이고, X 1 is O or S,
Z1 내지 Z3은 각각 독립적으로 N 또는 CRa이고, Z 1 to Z 3 are each independently N or CR a ,
Z1 내지 Z3 중 적어도 둘은 N이고, At least two of Z 1 to Z 3 are N,
L1 내지 L3은 각각 독립적으로 단일결합, 또는 치환 또는 비치환된 C6 내지 C20 아릴렌기이고, L 1 to L 3 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,
A1 및 A2는 각각 독립적으로 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C2 내지 C30 헤테로고리기이고, A 1 and A 2 are each independently a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
A1 및 A2 중 적어도 하나는 치환 또는 비치환된 C6 내지 C30 아릴기이고,At least one of A 1 and A 2 is a substituted or unsubstituted C6 to C30 aryl group,
Ra 및 R1 내지 R3은 각각 독립적으로 수소， 중수소, 사아노기, 치환 또는 비치환된 C1 내지 C10 알킬기, 또는 치환 또는 비치환된 C6 내지 C20 아릴기이고, 상기 화학식 2 및 3.에서, R a and R 1 to R 3 are each independently hydrogen, deuterium, sarano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C20 aryl group, and in Chemical Formulas 2 and 3.
Ar2는 치환 또는 비치환된 C6 내지 C20 아릴기이고, Ar 2 is a substituted or unsubstituted C6 to C20 aryl group,
화학식 2의 인접한 2개의 *은 화학식 3과 연결되고, Two adjacent * of Formula 2 are linked to Formula 3,
화학식 3과 연결되지 않은 화학식 2의 *은 각각 독립적으로 C-La-Rb이고, La, Y1 및 Y2는 각각 독립적으로 단일결합， 또는 치환 또는 비치환된 C6 내지 C20 아릴렌기이고，
Rb 및 R6 내지 R12는 각각 독립적으로 수소, 중수소, 시아노기， 치환 또는 비치환된 C1 내지 C10 알킬기， 또는 치환 또는 비치환된 C6 내지 C20 아릴기이다. * In Formula 2, which is not linked to Formula 3, is each independently CL a -R b , and L a , Y 1 and Y 2 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group, R b and R 6 to R 12 are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C20 aryl group.
【청구항 13 ] 【Claim 13】
제 12항에 있어서, The method of claim 12,
상기 게 1 호스트는 하기 화학식 1- 1로 표현되고， The crab 1 host is represented by the following Chemical Formula 1-1,
상기 제 2 호스트는 하기 화학식 2C로 표현되는 적색 인광 호스트용 조성물: The second host is a red phosphorescent host composition represented by the formula 2C:
[화학식 1- 1 ] 화학식 2C] [Formula 1-1] Formula 2C]
상기 화학식 1_ 1 및 화학식 2C에서, In Formula 1_ 1 and Formula 2C,
X1는 O또는 S이고, X 1 is O or S,
Z1 내지 Z3은 각각 독립적으로 N 또는 CRa이고, Z 1 to Z 3 are each independently N or CR a ,
Z1 내지 Z3 중 적어도 둘은 N이고, At least two of Z 1 to Z 3 are N,
L1 내지 L3, Lal, La2, Y1 및 Y2는 각각 독립적으로 단일결합, 또는 치환 또는 비치환된 C6 내지 C20 아릴렌기이고, L 1 to L 3 , L al , L a2 , Y 1 and Y 2 are each independently a single bond or a substituted or unsubstituted C6 to C20 arylene group,
A2는 치환 또는 비치환된 C6 내지 C30 아릴기, 또는 치환 또는 비치환된 C2 내지 C30 해테로고리기이고， A 2 is a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heterocyclic group,
Ar2는 치환 또는 비치환된 C6 내지 C30 아릴기이고, Ar 2 is a substituted or unsubstituted C6 to C30 aryl group,
Ra, Rbl, Rb2 및 R1 내지 R12는 각각 독립적으로 수소, 중수소, 시아노기， 치환 또는 비치환된 C1 내지 C10 알킬기, 또는 치환 또는 비치환된 C6 내지 C20 아릴기이다. R a , R bl , R b2 and R 1 to R 12 are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C20 aryl group.
【청구항 14】 [Claim 14]
제 13항에 있어서, The method of claim 13,
상기 제 1 호스트는 하기 화학식 1- 1 B-1 또는 화학식 1- I B-2로 표현되는 적색 인광 호스트용 조성물:
1- I B-l] [화학식 1- I B-2] The first host is a red phosphorescent host composition represented by the following Formula 1-1 B-1 or Formula 1-1 I-2: 1-I Bl] [Formula 1-I B-2]
상기 화학식 1- l B-l, 화학식 1- I B-2에서, In Chemical Formulas 1-1 B-1 and 1-1 I-2,
Ar1은 치환 또는 비치환된 페닐기, 치환 또는 비치환된 바이페닐기, 치환 또는 비치환된 나프틸기, 치환 또는 비치환된 터페닐기， 또는 치환 또는 비치환된 쿼터페닐기이고， Ar 1 is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted quarterphenyl group,
X1 및 X2는 각각 독립적으로 O 또는 S이고， X 1 and X 2 are each independently O or S,
Z1 내지 Z3은 각각 독립적으로 N 또는 CRa이고， Z 1 to Z 3 are each independently N or CR a ,
Z1 내지 Z3 중 적어도 둘은 N이고, At least two of Z 1 to Z 3 are N,
L1 내지 L3은 각각 독립적으로 단일결합, 또는 치환 또는 비치환된 C6 내 C20 아릴렌기이고, L 1 to L 3 are each independently a single bond or a substituted or unsubstituted C20 arylene group in C6,
Rc, Rd, Re 및 R1 내지 R5는 각각 독립적으로 수소, 중수소, 시아노기， 치환 또는 비치환된 C1 내지 C10 알킬기, 또는 치환 또는 비치환된 C6 내지 C20 아릴기이다. R c , R d , R e and R 1 to R 5 are each independently hydrogen, deuterium, cyano group, substituted or unsubstituted C1 to C10 alkyl group, or substituted or unsubstituted C6 to C20 aryl group.
【청구항 15】 [Claim 15]
게 1항 내지 제 11항 중 어느 한 항에 따른 유기 광전자 소자를 포함하는 표시장치.
A display device comprising the organic optoelectronic device according to any one of claims 1 to 11.
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| CN201880025006.0A CN110520504B (en) | 2017-05-26 | 2018-05-25 | Composition for phosphorescent host, organic optoelectronic device and display device |
| US16/498,616 US20210111350A1 (en) | 2017-05-26 | 2018-05-25 | Phosphorescent host composition, organic optoelectronic diode, and display device |
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| KR20170065468 | 2017-05-26 | ||
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| KR10-2018-0057825 | 2018-05-21 | ||
| KR1020180057825A KR102232510B1 (en) | 2017-05-26 | 2018-05-21 | Composition for phosphorescent host, organic optoelectronic device and display device |
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