TW200846441A - Fluorescence main host material and organic electroluminescence device using the material - Google Patents
Fluorescence main host material and organic electroluminescence device using the material Download PDFInfo
- Publication number
- TW200846441A TW200846441A TW096117650A TW96117650A TW200846441A TW 200846441 A TW200846441 A TW 200846441A TW 096117650 A TW096117650 A TW 096117650A TW 96117650 A TW96117650 A TW 96117650A TW 200846441 A TW200846441 A TW 200846441A
- Authority
- TW
- Taiwan
- Prior art keywords
- layer
- inv
- fluorescent
- light
- transport layer
- Prior art date
Links
- 239000000463 material Substances 0.000 title claims abstract description 67
- 238000005401 electroluminescence Methods 0.000 title abstract description 8
- 239000002019 doping agent Substances 0.000 claims abstract description 19
- 239000000126 substance Substances 0.000 claims abstract description 11
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims abstract description 3
- 238000002347 injection Methods 0.000 claims description 10
- 239000007924 injection Substances 0.000 claims description 10
- 230000005525 hole transport Effects 0.000 claims description 9
- 239000000758 substrate Substances 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000010410 layer Substances 0.000 description 47
- 239000007787 solid Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 238000001228 spectrum Methods 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000005516 engineering process Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 230000003595 spectral effect Effects 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 238000000103 photoluminescence spectrum Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 230000005284 excitation Effects 0.000 description 5
- 238000004020 luminiscence type Methods 0.000 description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 238000010586 diagram Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 241000234282 Allium Species 0.000 description 3
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- -1 hydroxyquinoline aluminum Chemical compound 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 102220043690 rs1049562 Human genes 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- 238000007738 vacuum evaporation Methods 0.000 description 3
- COHYTHOBJLSHDF-UHFFFAOYSA-N Indigo Chemical compound N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 241000333779 Thunbergia battiscombei Species 0.000 description 2
- 150000004984 aromatic diamines Chemical class 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 238000000695 excitation spectrum Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-UHFFFAOYSA-N 0.000 description 1
- 235000017166 Bambusa arundinacea Nutrition 0.000 description 1
- 235000017491 Bambusa tulda Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 229910000861 Mg alloy Inorganic materials 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 244000082204 Phyllostachys viridis Species 0.000 description 1
- 235000015334 Phyllostachys viridis Nutrition 0.000 description 1
- 229910052778 Plutonium Inorganic materials 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 description 1
- 239000011425 bamboo Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 229920000547 conjugated polymer Polymers 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- DCZFGQYXRKMVFG-UHFFFAOYSA-N cyclohexane-1,4-dione Chemical compound O=C1CCC(=O)CC1 DCZFGQYXRKMVFG-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- OYEHPCDNVJXUIW-UHFFFAOYSA-N plutonium atom Chemical compound [Pu] OYEHPCDNVJXUIW-UHFFFAOYSA-N 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/56—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed
- C07C15/58—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed containing two rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/56—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed
- C07C15/60—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals polycyclic condensed containing three rings
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
- H10K50/156—Hole transporting layers comprising a multilayered structure
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/624—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing six or more rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
200846441 九、發明說明: 【發明所屬之技術領域】 本發明係關於一種螢光主發光體材料,更進一步地, 本發明係關於一種使用前述螢光主發光體材料之高發光效 ' 率之有機電激發光裝置。 【先前技術】 近來有機半導體與有機導電材料的被熱烈地研究,尤 Φ 其是使用有機半導體之發光元件之有機電冷光裝置已具有 顯者地進步。有機電激發光(organic electroluminescence, OEL)是指在一定電場下,有機物質被相應的電能激發所發 生的發光現象。1963年P〇pel等人在研究1〇〜20 //m厚的 蔥(anthracene)單晶片時首先發現在晶體兩端施以400伏特 電壓後,可觀察到蔥發出藍色螢光,使得有機電激發光的 研究跨出了第一步,但由於單晶成長、大面積化困難,且 所需的驅動電壓太大,發光效率又較無機材枓差,因此不 具實用價值。隨後Helfrich和Williams等人繼續努力研究, φ 將電壓降至1〇0伏特左右,獲得了約5 %光子/電子的外部 、 量子效率,但由於單晶厚度還是過大,因而使得驅動電壓 • 也較高,造成電能轉化成光能的效率太低。1982年Vincett 等人利用真空蒸鍍法製成了僅50 nm厚的蔥薄膜,進一步 將驅動電壓降至30伏特即能觀察到藍色螢光,不過由於電 子注入效率太低及蔥的成膜性不好,所以其外部量子效率 只有0·03 %左右。之後雖經過二十多年的零星發展,卻仍 一直未有重大突破。 直到1987年美國柯達公司(Eastman Kodak company) Tang及VanSlyke等人首先發表有機發光二極體(〇rganic 5 200846441 light-emitting diodes,OLEDs),才有突破性的發展。他們將 芳香二胺(HTM-2)作為電洞傳輸層材料,和成膜性好的& 羥基喹啉鋁 Alq3 (tris(84iydroxyquinolinato)aluminum(III)) =為電=傳輸層和發光材料利用真空蒸鍍製成6〇〜7〇11111的 . 薄膜,並以低功函數的鎂銀合金為陰極,提高電子和電洞 的注入效率。在兩片電極間置入其所開發的有機小分子發 光材料,通電即可發出光來,其產生波長為53〇nm的綠光, 可展現出低驅動電壓、高量子效率(> 丨%)及元件穩定性等 效果,大幅提升有機小分子電激發光元件的特性與實用性。 其後1990年’英國劍橋大學(cambridge University) Friend等人接著發表高分子發光二極體(polymer light-emitting diodes ’ PLEDs),以旋轉塗佈的方式,將共輛 咼分子 PPV (p〇ly(p-phenylene vinylene))當作發光層,製作 出單層結構的聚合物電激發光元件,由於其具有製程簡 單、咼分子良好的機械性質及似半導體的特性,使得共軛 高分子發光材料方面的研究快速發展。 值得注意的是,比起目前以LCD為主流的FPD,OLED φ 不但能自發光,不需要背光模組,且具有低驅動電壓、高 • 亮度、高對比、廣視角、響應速度快、結構簡單、超薄膜、 • 重量輕等優點,可有效應用於照明或製成顯示器、光電偶 合器等地方,若製作在如塑膠基板的柔軟襯底上,器件便 可彎曲、折疊便於攜帶,而且由於製程簡單,預計可大幅 降低成本。目前已吸引全球超過八十家公司競相投入巨資 研發有機電激發光顯示器技術,也因而成為另一顯示技術 的主流。 1997年,日本Pi〇neer公司首先發表一款低分子系的單 色(綠色)被動式顯示器,成功地將有機電激發光顯示技 200846441200846441 IX. INSTRUCTIONS OF THE INVENTION: TECHNICAL FIELD The present invention relates to a fluorescent main illuminant material, and further, the present invention relates to a high luminescence efficiency of using the aforementioned fluorescent main illuminant material. Electromechanical excitation device. [Prior Art] Recently, organic semiconductors and organic conductive materials have been enthusiastically studied, and in particular, organic light-cooling devices using light-emitting elements of organic semiconductors have been remarkably improved. Organic electroluminescence (OEL) is a phenomenon in which an organic substance is excited by a corresponding electric energy under a certain electric field. In 1963, when P〇pel et al. studied a single-wafer of anthracene of 1〇20-20m thick, it was first discovered that after applying 400 volts across the crystal, it was observed that the onion emits blue fluorescence, so that The research on electromechanical excitation light has taken the first step. However, due to the difficulty in growing single crystal and large area, and the required driving voltage is too large, the luminous efficiency is inferior to that of inorganic materials, so it has no practical value. Subsequently, Helfrich and Williams and others continued their efforts to study, φ reduced the voltage to about 1 〇 0 volts, obtained about 5% of the photon / electron external, quantum efficiency, but because the thickness of the single crystal is still too large, so the driving voltage is also High, the efficiency of converting electrical energy into light energy is too low. In 1982, Vincett et al. made a 50 nm thick onion film by vacuum evaporation, and further reduced the driving voltage to 30 volts to observe blue fluorescence, but the electron injection efficiency was too low and the onion film formation. The sex is not good, so its external quantum efficiency is only about 0.03%. After more than 20 years of sporadic development, there have been no major breakthroughs. It was not until 1987 that Eastman Kodak company Tang and Van Slyke first published organic light-emitting diodes (〇rganic 5 200846441 light-emitting diodes, OLEDs) that they had a breakthrough. They use aromatic diamine (HTM-2) as the material for the hole transport layer, and the film-forming property & hydroxyquinoline aluminum Alq3 (tris(84iydroxyquinolinato)aluminum(III)) = electricity = transport layer and luminescent material utilization The film is formed by vacuum evaporation to a film of 6 〇 to 7 〇 11111, and a magnesium alloy with a low work function is used as a cathode to improve the injection efficiency of electrons and holes. The organic small molecule luminescent material developed by the two electrodes is placed between them to emit light, which generates green light with a wavelength of 53 〇nm, which can exhibit low driving voltage and high quantum efficiency (> 丨% ) and the stability of components, etc., greatly improve the characteristics and practicality of organic small molecule electroluminescent devices. Then in 1990, Friend et al., Cambridge University, UK, subsequently published polymer light-emitting diodes (PLEDs), which spin-coated a total of plutonium molecules PPV (p〇ly (p-phenylene vinylene)) as a light-emitting layer, a polymer electroluminescent device having a single-layer structure, which has a simple process, good mechanical properties of a ruthenium molecule, and semiconductor-like properties, so that a conjugated polymer luminescent material is obtained. Research in the field has developed rapidly. It is worth noting that OLED φ not only self-illuminates, but also does not require a backlight module, and has low driving voltage, high brightness, high contrast, wide viewing angle, fast response, and simple structure compared to the current FPD with LCD as the mainstream. , ultra-thin film, • light weight and other advantages, can be effectively applied to lighting or made into displays, photoelectric couplers, etc. If fabricated on a flexible substrate such as a plastic substrate, the device can be bent, folded and portable, and due to the process Simple, it is expected to significantly reduce costs. At present, more than 80 companies around the world have been attracted to invest heavily in the development of organic electroluminescent display technology, which has become the mainstream of another display technology. In 1997, Pi〇neer of Japan first published a low-molecular monochromatic (green) passive display that successfully used organic electroluminescent display technology.
術,實用地應用在汽車儀器面板上。此後有機電激發光顯 示器開始產品化,陸續被應用在小尺寸的面板上,像1998 年曰本TDK公司,2002年銖寶科技,三星,NTTDo Co Mo 的彩色手機’ 2003年柯達數位相機等。日本pi〇neer公司與 柯達Kodak也合作小!量產〇LED單色及多色(monochrome and multicolor)的顯示器,目前已正式應用在Motorola手機 上,頗獲好評;而Sanyo亦與柯達合作,製作出小尺寸的 全彩(full color) OLED樣品,宣稱於2〇〇1年後量產;奇美 公司更發表了主動式的10吋以上的彩色顯示器,使得有機 電激發光技術更跨進一步。不過,至目前為止,仍有 其須進一步改善之處,包括其色飽和度、穩定度、發光效 率和壽命等等,此與材料本身的性質和製程息息相關,若 能突破應能期許成為未來顯示器的趨勢。 發光材料在有機電激發光元件中是最重要的材料,好 的發光材料必需滿足四個條件··高量子效率的螢光特 性,且螢光光譜主要分佈在400〜700 nm可見光區域内·,(2) 良好的半導體特性,具有高的導電率,能傳導電子或電洞, 或者兩者皆有;(3)良好的成膜性,在幾十奈米的薄膜中 會產生針孔;(4)良好的熱穩定性。 ' 大部份的電子傳輸層和電洞傳輸層都可作為可見光區 的發光材料,由於大多數的有機材料在超過一定濃度, 其是固悲時’會存在自我驟媳(selfquenehing)或稱濃度驟炉 (concentmtion quenching)的問題,導致發射峰變寬或3 = 紅位移’所以-般會以低濃度的方式將螢光摻^ (doping)在具某種載流子性質的螢光主發光體材…由 作為客發光體(dopant emitter)。應用在有機電激笋 认 螢光主發光體材料與螢光摻雜物之幾個設計考慮為:(1)技 200846441 與m二有鬲的螢光效率;(2)螢光摻雜物的吸收光譜和 a光發光體材料的發射光譜要有很好的重疊,使能量 以有效地從主體傳遞到客體;(3)有紅 射峰’且發射峰盡可能的窄以維持光色的純度f(4== 好,能蒸鍍。 ()%疋性 近幾年業界致力於有機電激發光材料的研究,么一 了不錯的成果。紅、藍、綠是光的三原色,好的二、、二有 率及純色是達到全彩顯示器的基本重要需求。在^束色致 =產之制2GG!_335516之專利公開案中,揭示了—種g ,激發光元件,其發光層之螢光主發光體材料結構係二=It is applied practically on the panel of automotive instruments. Since then, the organic electroluminescent display has been commercialized and has been applied to small-sized panels, such as the 1998 TDK Corporation, 2002 Sic Bo Technology, Samsung, NTT Do Co Mo's color mobile phone, 2003 Kodak digital camera. Japan pi〇neer company and Kodak Kodak also cooperate small! The production of 单色LED monochrome and multicolor displays has been officially applied to Motorola phones, and Sanyo has also collaborated with Kodak to produce small-size full color OLED samples. It claims to be mass-produced after 2 〇〇 1 year; Chi Mei Company has also released an active color display of more than 10 inches, making the organic electro-excitation technology more advanced. However, until now, there are still some areas for further improvement, including its color saturation, stability, luminous efficiency and longevity. This is closely related to the nature and process of the material itself. If it can break through, it should be expected to become a future display. the trend of. The luminescent material is the most important material in the organic electroluminescent device. A good luminescent material must satisfy the four conditions · high quantum efficiency fluorescence characteristics, and the fluorescence spectrum is mainly distributed in the visible light region of 400 to 700 nm. (2) Good semiconductor characteristics, high conductivity, ability to conduct electrons or holes, or both; (3) good film formation, pinholes in tens of nanometer films; 4) Good thermal stability. 'Most of the electron transport layer and the hole transport layer can be used as luminescent materials in the visible region. Since most organic materials exceed a certain concentration, they are self-sufficient or self-sufficient. The problem of concentmtion quenching leads to a broadening of the emission peak or a 3 = red shift. Therefore, the fluorescence is doped in a low concentration manner in a fluorescent main luminescence with a certain carrier property. The body... is used as a dopant emitter. Several design considerations for the use of organic electroluminescent bamboo shoots to fluoresce the main illuminant materials and fluorescent dopants are: (1) technology 200846441 and m two have fluorescent efficiency; (2) fluorescent dopants The absorption spectrum and the emission spectrum of the a-light emitter material should have a good overlap, so that the energy is efficiently transmitted from the host to the guest; (3) there is a red peak ' and the emission peak is as narrow as possible to maintain the purity of the light color. f(4== Good, can be evaporated. ()%疋In recent years, the industry has devoted itself to the research of organic electroluminescent materials. It has a good result. Red, blue and green are the three primary colors of light, good two. The second rate and the solid color are the basic requirements for achieving a full-color display. In the patent publication of 2GG!_335516, which produces a color, the excitation element, and the luminescent layer of the luminescent layer are disclosed. Light main illuminant material structure two =
m 柯達公司之美國專利編號US-2005089717揭示了 — 有機電激發光元件,其發光層之螢光主發光體材料社^種 如下: 〜攝係 8 200846441U.S. Patent No. US-A-0,050,0,058,017 to Kodak Corporation discloses an organic electroluminescent device, and a fluorescent main illuminant material of the luminescent layer is as follows: ~ Photograph 8 200846441
S4 然此專利之發明物與本案之妹 同,且此專利揭示之藍色螢光換=構式不同,光電特性不 光體材料(其CIEy>0.18)之用。多雜物並非作為深藍色主發S4 However, the invention of this patent is the same as the sister of the present invention, and the blue fluorescent conversion structure disclosed in this patent is different, and the photoelectric characteristic is not the material (CIEy > 0.18). Many debris is not as a deep blue main hair
此外,Covion公司之歐盟專 滎光波長較紅深藍色$光林*=655359揭示了 一種 雜物搭配使料,可有效提材料’當其與榮光捧 命。然而’此專利所請之材料物之發光效率與壽 其異構物的分離純化誠屬不易:::點’亦即該材料與 有較短之螢絲譜性質。 且只有其中-個異構物才具In addition, Covion's European Union's special wavelength of light is deeper than the deep blue. $光林*=655359 reveals a kind of miscellaneous material that can effectively raise the material 'when it is with glory. However, the luminescence efficiency of the materials requested in this patent and the separation and purification of the isomers are not easy::: The material is associated with a shorter spectral property. And only one of them is
針對先雨技術的缺點,本發明嘗試開發一種螢光主發 光體材料,其最咼已填滿分子執域與最低未填滿分子執域 (HOMO/LUMO)間具有較寬之能階差,使其具有較深藍 色之光激發頻谱(photoluminesent spectrum,PL),進而可 使其與深藍色螢光摻雜物(具較短紫外線吸收頻譜與較短 之螢光發光頻譜之材料)間具有較佳之能量轉換效率 (spectral overlap integral,J),提高有機電激發光裝置之發 光效率。 9 200846441 【發明内容】 有鑑於先前技術之缺失,本發明之目的 光主發光體材料。相較於習知之螢光主發,供一種螢 明之榮光主發光體材料具有提升色C,本發 政率、高壽命以及容易合成與純化等優點。’物之發光 A本發明之另一目的係提供一種高發光效率之备 :以該發光裝置的⑽^In view of the shortcomings of the prior rain technology, the present invention attempts to develop a fluorescent main illuminant material, which has a wide energy difference between the last filled domain and the lowest unfilled domain (HOMO/LUMO). It has a deep blue light photoluminescence spectrum (PL), which in turn can be combined with a deep blue fluorescent dopant (a material with a shorter ultraviolet absorption spectrum and a shorter fluorescent emission spectrum). The preferred spectral overlap integral (J) improves the luminous efficiency of the organic electroluminescent device. 9 200846441 SUMMARY OF THE INVENTION In view of the deficiencies of the prior art, the object of the present invention is a light-based illuminant material. Compared with the conventional fluorescent main hair, the luminescent light main illuminant material has a lifting color C, the aging rate, high life and easy synthesis and purification. 'Lighting of matter' A another object of the present invention is to provide a high luminous efficiency: (10)^ of the light-emitting device
下 為達上述目的,本發明之螢光主發光體材料 列化學式(I)或(II)所示之結構: ’、/、有In order to achieve the above object, the fluorescent main light-emitting material of the present invention has a structure represented by the chemical formula (I) or (II): ', /,
JL 中,Δ , (H); f Ah和Ah係獨立代表苯基、卜萘基或2茇 在車乂么實施態樣中,本發明 斤、基 下列化學式所社化合物:月之^主發切材料係 200846441In JL, Δ , (H); f Ah and Ah are independent representatives of phenyl, naphthyl or 2 茇 in the implementation of the rut, the present invention, the following chemical formula: the main ^ cutting material Department 200846441
特徵在於發光層中包含前述螢光主發光體材料。 在較佳實施態樣中’本發明之有機電激發光裝置之發 光層中進一步包含一深藍色螢光摻雜物,該深藍色螢光摻 雜物較佳具有在 Commission Internationale d' Exclairage (ClEx,y)座標中具有 CIExS0.15,CIEyS0.18 之特性。 11 200846441 在更佳之具體實施態樣中,本發明之有機電激發光裝 置之發光層包含下列化學式所示之深藍色螢光摻雜物:It is characterized in that the above-mentioned fluorescent main illuminant material is contained in the luminescent layer. In a preferred embodiment, the luminescent layer of the organic electroluminescent device of the present invention further comprises a deep blue fluorescent dopant, preferably having a deep blue fluorescent dopant at Commission Internationale d' Exclairage (ClEx , y) coordinates have CIExS0.15, CIEyS0.18. 11 200846441 In a more preferred embodiment, the luminescent layer of the organic electroluminescent device of the present invention comprises a deep blue fluorescing dopant of the formula:
f ( BD-2 )。 【實施方式】 本發明之螢光主發光體材料係具有下列化學式⑴或(II) 所示之結構:f ( BD-2 ). [Embodiment] The fluorescent main light-emitting material of the present invention has a structure represented by the following chemical formula (1) or (II):
12 (I), 20084644112 (I), 200846441
Αϊ2 (II); 其中二ΑΓι* Ah係獨立代表苯基、萘基或2_萘基。 _在目前有機電激發光裝置的發光層材料選用上,通常 會使用一螢光主發光體材料搭配一營光捧雜物之設計來達 到电放發光之效果,因此在有機電激發光材料的設計與選 用上 >’首先需考慮的是材料分子的光色與分子螢光或磷光 轉化效率’基於上述目的’必須充分瞭解分子之執域狀態, 例如構型對轨域重疊性的影響。 ^ ,發明之螢光主發光體材料在結構上的特點係在7Γ — 包子系統中设计引入萘基_9_蒽官能基,藉此改變分子光 電特性。由於1-萘基和蒽之間會產生較大的立體障礙空間 (例如,,,前技術中之螢光主發光體材料ADN和本發明 φ 之材料來汁异,本發明之萘基和蒽之間的扭轉角為86.477 而ADN之2-萘基和蒽之間的扭轉角為74 956。),所以 1 ^基_9_恩官能基對非定域化冗_系統會產生影響,使骨 架二^之電子密度下降,進而導致最高被佔有執域(Ή〇Μ〇 ) =能階下,,而達到增加HOMO/LUMO能隙的目的。是以, 2以1-萘基-9-蒽官能基作為螢光主發光體材料之取代基 %,該基可使本發明之一系列螢光主發光體材料衍= 物具有/朱監色光激發頻譜(photoluminesent spectrum,PL )。 在較佳實施態樣中,本發明之螢光主發光體 下列化學式所示之化合物: 叶係為 13 200846441Αϊ 2 (II); wherein ΑΓι* Ah is independently represented by phenyl, naphthyl or 2-naphthyl. _ In the current selection of the luminescent layer material of the organic electroluminescent device, a fluorescent main illuminant material is usually used together with the design of a camping light to achieve the effect of the electroluminescence, so that the organic electroluminescent material is Design and selection > The first thing to consider is that the color and molecular fluorescence or phosphorescent conversion efficiency of the material molecule 'based on the above objectives' must fully understand the domain state of the molecule, such as the effect of the configuration on the overlap of the orbital domain. ^, The structural characteristics of the inventive phosphorescent illuminant material are designed to introduce a naphthyl _9_ fluorene functional group in the 7 Γ-package subsystem, thereby changing the molecular photovoltaic properties. Since a large steric hindrance space is generated between 1-naphthyl and anthracene (for example, the fluorescent main light-emitting material ADN of the prior art and the material of the present invention φ are different, the naphthyl group and the anthracene of the present invention) The twist angle between the two is 86.477 and the twist angle between the 2-naphthyl and anthracene of ADN is 74 956.), so the 1 ^ base _9_en functional group has an effect on the non-localized redundancy system. The electron density of the skeleton II decreases, which leads to the highest occupied domain (Ή〇Μ〇) = energy level, and the purpose of increasing the HOMO/LUMO energy gap is achieved. Therefore, 2 is a 1-naphthyl-9-fluorene functional group as a substituent of the fluorescent main illuminant material, and the group can be used as a series of fluorescent main illuminant materials of the present invention. Photoluminesent spectrum (PL). In a preferred embodiment, the fluorescent primary illuminator of the present invention is a compound of the following chemical formula: the leaf system is 13 200846441
、、上u冓之本發明之化合物之能隙Eg^3 〇〇eV,使其 成為具有深藍色光激發頻譜,可作為深藍光主發光體材& 之用途。 在本發明之有機電激發光裝置,其係包含依以下順序 排列之層狀結構:透明基板、陽極層、電洞傳輸層、發光 層、電子傳輸層及陰極層;其中,陽極層及陰極層係&別 與外部電源接觸形成電通路,且除發光廣以外之各層,盆 他各層材料之選用係屬本技術領域之通常知識而無須限 定,例如透明基板係可為具光穿透特性之不可撓玻璃基板 200846441 或者具可撓性之透明有機高分子材料;又如陽極層係可為 氧化銦錫(ΙΤΌ)等。 本發明之有機電激發光裝置其特徵在於發光層中包含 前述螢光主發光體材料。 在較佳實施態樣中,陽極層和電洞傳輸層之間係可進 一步包含一電洞注入層;電子傳輸層和陰極層之間係進一 步包含一電子注入層,其中,電洞注入層與電子注入層之 材料亦屬本技術領域之通常知識而無須限定。 φ 在較佳實施癌樣中,本發明之有機電激發光裝置之發 光層中進一步包含深藍色螢光摻雜物,選用之深藍色螢光 雜物較仏係具有在C〇mmissi〇n jnternati〇naie d Exclairage( CIEx,y )座標中具有 CIEx $ 〇 · i 5,CIEy ‘ 〇 ] 8 特性,這些深藍色螢光摻雜物之共同特性係具有較短之紫 外線吸收頻譜,以及較短之螢光發光頻譜。 二+由於本發明之螢光主發光體材料2H〇m〇/lum〇能隙 車乂見,使之具有洙藍色光激發頻譜。而依照抑如以能量轉 移機制,本發明之螢光主發光體材料對於深藍色榮光換雜 • 物具有較佳之能量轉換效率(spectral overlap integrd,J ), • 也因此能夠提高深藍色螢光摻雜物之發光效率與壽命。適 ,用於本發明之有機電激發光農置之發光層中之深藍色榮光 ,雜物之具義樣包含,但不限於下列化學式所示之化合 物:The energy gap Eg^3 〇〇eV of the compound of the present invention is used to have a deep blue light excitation spectrum and can be used as a deep blue light-emitting material & The organic electroluminescent device of the present invention comprises a layered structure arranged in the following order: a transparent substrate, an anode layer, a hole transport layer, a light emitting layer, an electron transport layer and a cathode layer; wherein the anode layer and the cathode layer The system & does not contact the external power source to form an electrical path, and in addition to the wide range of light emission, the selection of the material of each layer of the pot is a common knowledge in the art without limitation, for example, the transparent substrate can be light transmissive. The inflexible glass substrate 200846441 or a flexible transparent organic polymer material; and the anode layer may be indium tin oxide or the like. The organic electroluminescent device of the present invention is characterized in that the above-mentioned fluorescent main emitter material is contained in the light-emitting layer. In a preferred embodiment, the anode layer and the hole transport layer may further comprise a hole injection layer; the electron transport layer and the cathode layer further comprise an electron injection layer, wherein the hole injection layer and The material of the electron injecting layer is also a common knowledge in the art without limitation. φ In the preferred embodiment of the cancer, the luminescent layer of the organic electroluminescent device of the present invention further comprises a deep blue fluorescent dopant, and the dark blue fluorescing impurity selected is more than the lanthanide in C〇mmissi〇n jnternati The 〇naie d Exclairage (CIEx,y) coordinates have CIEx $ 〇· i 5,CIEy ' 〇] 8 characteristics. The common characteristics of these dark blue fluorescent dopants are shorter UV absorption spectrum and shorter Fluorescent spectrum. The second ++ is due to the 2H〇m〇/lum〇 energy gap of the fluorescent main illuminant material of the present invention, which has an indigo blue excitation spectrum. According to the energy transfer mechanism, the fluorescent main emitter material of the present invention has better energy conversion efficiency (spectral overlap integrd, J) for the deep blue glory, and thus can improve the dark blue fluorescent blend. Luminous efficiency and longevity of debris. Suitable for use in the dark blue glory of the organic electroluminescent light-emitting layer of the present invention, the inclusions of the impurities include, but are not limited to, the compounds shown by the following chemical formulas:
(BD-1,TBPE)或 200846441(BD-1, TBPE) or 200846441
f (BD-2) 〇 以下實施態樣制於進_步了解本發明之優點 用於限制本發明之申請專利範圍。 1非 φ 實施例L本發明之螢光主發光艘材料之合成 2-(3T-溴-聯茉-4-某萘之合$f (BD-2) 〇 The following embodiments are described in the following paragraphs to understand the advantages of the present invention. 1 non-φ Example L Synthesis of the fluorescent main light-emitting material of the present invention 2-(3T-Bromo-Lianmu-4-Naphthalene
OHOH
在氮氣下置入10.52克2-(4-硼酸-苯基)-萘、1〇克碟 ->臭本、11·6克碳酸鉀(先溶於35 ml水中)、100 mi四气〇夫 • 喃和0·8克四(三苯基膦)鈀,迴流反應隔夜(20小時厂A 卻,加水逼出固體,過濾取固體、烘乾,曱笨再結晶,^ ,遽取固體,烘乾得成品6.75克,純度98.1%,收率53 5% °。 [HPLC 條件]管柱:Rjp-8,流速:1·0 ml/分鐘,CH3CN : Η2〇=8 · 2 2-(4^溴-聯苯-4-基V萘之合成Under nitrogen, put 10.52 g of 2-(4-boronic acid-phenyl)-naphthalene, 1 gram of disc-> stinky, 11.6 g of potassium carbonate (dissolved in 35 ml of water first), 100 mi of tetragas Fu and 0. 8g of tetrakis(triphenylphosphine)palladium, reflux reaction overnight (20 hours plant A, add water to force solids, filter to take solids, dry, stupid and recrystallize, ^, extract solids, The finished product was dried up to 6.75 g, purity 98.1%, yield 53 5% ° [HPLC conditions] column: Rjp-8, flow rate: 1·0 ml/min, CH3CN: Η2〇=8 · 2 2-(4 Synthesis of bromine-biphenyl-4-yl V naphthalene
16 200846441 在氮氣下置入10.55克2-(4-硼酸-苯基)-萘、10克各破 -溴苯、η·7碳酸鉀(先溶於35ml水中),100〇11四氫吱喝 和0·8克四(二苯基膦)飽,迴流反應隔夜(2〇小時),冷卻, 加水逼出固體,過濾取固體、烘乾,甲苯再結晶,^濾取 固體’烘乾传成品7· 19克,純度98.5%,收率57·〇%。 基-聯笼某-3-基Vt 之合成16 200846441 Under nitrogen, put 10.55 g of 2-(4-boronic acid-phenyl)-naphthalene, 10 g of each broken-bromobenzene, η·7 potassium carbonate (dissolved in 35 ml of water first), 100〇11 tetrahydroquinone And 0. 8 g of tetrakis(diphenylphosphine) saturated, reflux reaction overnight (2 hrs), cooling, adding water to extract solids, filtering to take solids, drying, toluene recrystallization, ^ filter solids 'drying finished products 7·19 g, purity 98.5%, yield 57·〇%. Synthesis of a group-linked cage -3-yl Vt
在氮氣下置入5克2-(3,-溴-聯苯基_4_基)_萘、5.81克 9-硼酸-10-萘-1-基_蒽、i〇〇mi四氫呋喃、4 61克碳酸鉀(先 溶於16.5 ml水)和〇·48克四(三苯基膦)纪,迴流反應4小 時,冷卻至室溫,將反應液倒入水中攪拌逼出固體,過濾 取固體’烘乾,以曱苯再結晶,冷卻,過濾,取固體,烘 乾,得成品4.55克,純度99.25%,收率56%。產品昇華純 化後純度 99.8%。溶點:301.4°C,Tg 點:141.7°C。 [HPLC 條件]管柱:Rp_8,流速:1.〇 mi/分鐘,CH3cN : 100% 4 NMR (400MHz)光譜數據:δ 8.05-8.09 (m,2H),8.01-8.03 (d,1H),7·82-7·91 (m,11H),7·68-7·76 (m,2H),7·57-7·59 (m,2H),7.41-7.54 (m,6H),7·32-7·35 (m,2H),7·16-7·25(πι,4Η) 17 200846441 3”-溴-「Ι,ΓΑ,ΓΊ聯三笨之合成5 g of 2-(3,-bromo-biphenyl-4-yl)-naphthalene, 5.81 g of 9-boronic acid-10-naphthalen-1-yl-indole, i〇〇mi tetrahydrofuran, 4 61 were placed under nitrogen. Potassium carbonate (dissolved first in 16.5 ml of water) and 〇·48 g of tetrakis(triphenylphosphine), refluxing for 4 hours, cooling to room temperature, pouring the reaction into water, stirring to solidify, and filtering for solids' Drying, recrystallizing with benzene, cooling, filtering, taking solid, drying, to obtain 4.55 g of finished product, purity 99.25%, yield 56%. The purity of the product after sublimation was 99.8%. Melting point: 301.4 ° C, Tg point: 141.7 ° C. [HPLC conditions] column: Rp_8, flow rate: 1. 〇mi/min, CH3cN: 100% 4 NMR (400 MHz) Spectral data: δ 8.05-8.09 (m, 2H), 8.01-8.03 (d, 1H), 7 ·82-7·91 (m,11H),7·68-7·76 (m,2H),7·57-7·59 (m,2H),7.41-7.54 (m,6H),7·32 -7·35 (m,2H),7·16-7·25(πι,4Η) 17 200846441 3”-Bromo--"Ι,ΓΑ,ΓΊ合三笨之合成
在氮氣下加入12.6克4-硼酸聯苯、15.0克3-姨-溴苯、 17.4克碳酸鉀(先溶於52·5 ml水)、75 ml四氫呋喃和2.75 φ 克四(三苯基膦)鈀,迴流反應隔夜(20小時),冷卻至室溫, 將反應液倒入水中攪拌逼出固體,過濾取固體,烘乾,以 曱苯再結晶,冷卻,過濾,取固體,烘乾,得成品8.2克, 純度98%,收率50%。 [HPLC 條件]管柱·· RP-8,流速:1.0 ml/分鐘,CH3CN : H20=8: 2 9_萘-1-基-10-『U’:4’J"1聯三茉-3-基-蔥(Inv2)之合成12.6 g of 4-boric acid biphenyl, 15.0 g of 3-indene-bromobenzene, 17.4 g of potassium carbonate (dissolved in 52.5 ml of water), 75 ml of tetrahydrofuran and 2.75 φ g of tetrakis(triphenylphosphine) were added under nitrogen. Palladium, reflux reaction overnight (20 hours), cooled to room temperature, the reaction solution was poured into water and stirred to solidify, solids were collected by filtration, dried, recrystallized with benzene, cooled, filtered, solid, dried, The finished product is 8.2 g, the purity is 98%, and the yield is 50%. [HPLC conditions] column ·· RP-8, flow rate: 1.0 ml/min, CH3CN: H20=8: 2 9_naphthalene-1-yl-10-"U':4'J"1 Liansanmo-3 - Synthesis of basal-onion (Inv2)
在氮氣下置入5克3”-溴-[1,Γ;4’,Γ]聯三苯、7.45克9-棚酸-10-蔡-1 -基_恩、100 ml四氮咬11 南、5.15克碳酸舒(先 溶於19 ml水)和0.56克四(三苯基膦)纪,迴流反應4小時, 冷卻至室溫,將反應液倒入水中攪拌逼出固體,過濾取固 體,烘乾,以甲苯再結晶,冷卻,過濾,取固體,烘乾, 18 200846441 得成品5·9克,純度99·2%,收率68.6%。產品昇華純化後 純度 99.7%。熔點:286.4°C,Tg 點:132.5°C。 [HPLC 條件]管柱:RP-8,流速:1·0 ml/分鐘,CH3CN : H20=95 : 5 hNMR (400MHz)光譜數據:δ 8.05-8.07 (d,1Η),8·00-8·02 (d,1Η),7.77-7.87 (m,6H),7.62-7.72 (m,6H),7·56·7·58 (m, 2H),7.43-7.53 (m,5H),7.31-7.35 (m,3H),7·19-7·24 (m,4H) • 1_-—(3Ά-聯苯基-4_農)_莕之合成5 g of 3"-bromo-[1, hydrazine; 4', hydrazine] triphenyl, 7.45 g of 9- phthalic acid-10-cai-1 -yl-en, 100 ml of tetrazole 11 South were placed under nitrogen. 5.15 g of carbonic acid (first dissolved in 19 ml of water) and 0.56 g of tetrakis(triphenylphosphine), refluxing for 4 hours, cooling to room temperature, pouring the reaction into water, stirring to solidify, and filtering to obtain a solid. Drying, recrystallization with toluene, cooling, filtration, taking solid, drying, 18 200846441 The finished product is 5·9 g, the purity is 99. 2%, the yield is 68.6%. The purity of the product after sublimation purification is 99.7%. Melting point: 286.4° C, Tg point: 132.5 ° C. [HPLC conditions] column: RP-8, flow rate: 1·0 ml/min, CH3CN: H20=95: 5 h NMR (400 MHz) spectral data: δ 8.05-8.07 (d, 1Η),8·00-8·02 (d,1Η),7.77-7.87 (m,6H),7.62-7.72 (m,6H),7·56·7·58 (m, 2H),7.43-7.53 (m,5H),7.31-7.35 (m,3H),7·19-7·24 (m,4H) • 1_-—(3Ά-biphenyl-4_农)_荇
HOHO
在氮氣下置入1〇·56克1-(4-硼酸-苯基)-萘,ΐ〇·〇2克3-蛾-溴苯,11·6碳酸鉀(先溶於35 ml水),1〇〇 ml四氫呋喃、 • 0·8克四(三苯基膦)鈀,迴流反應隔夜(20小時),冷卻,加 • 水逼出固體,過濾取固體、烘乾,甲苯再結晶,過濾取固 體’烘乾得成品7·32克,純度98.5%,收率58.0%。 g::萘-1-基-丄0-(4’_萘:1]_:蓋_聯笨基_3基)U ιην 3 )之合成 200846441 在亂氣下置入5.1克1-(3,备聯笨基·4_基)_蔡、5 9〇克 9-硼酸-10-萘-1备慧、100 ml四氫吱喃、4乃克碳酸鉀(先 ^於16.5 ml水)和0.49克四(三苯基騰)把,迴流反應4小 二Γ至室溫:將ί應液倒入水中授拌逼出固體,過渡 ^古^、烘乾’以甲苯再結晶,冷卻,過渡,取固體,供 乾,付成品4.71克’純度99.25%,收率58%。產品昇華純 化後純度99·6%。、溶點··抓代〜點:⑽宂 [HPLC條件]管柱:㈣,流速:U)m 100%1 〇·56 g of 1-(4-boronic acid-phenyl)-naphthalene, ΐ〇·〇2 g of 3-moth-bromobenzene, and 11.6 potassium carbonate (dissolved in 35 ml of water) were placed under nitrogen. 1〇〇ml tetrahydrofuran, • 0·8g of tetrakis(triphenylphosphine)palladium, reflux reaction overnight (20 hours), cooling, adding water to solidify, solid by filtration, drying, recrystallization of toluene, filtration The solid 'dryed the finished product 7.32 g, the purity was 98.5%, and the yield was 58.0%. g::naphthalene-1-yl-丄0-(4'-naphthalene:1]_: cap_linking base_3 base) U ιην 3) synthesis 200846441 Putting 5.1 g 1-(3) under chaos ,备联笨基·4_基)_Cai, 5 9 gram 9-boric acid-10-naphthalene-1 prepared hui, 100 ml tetrahydrofuran, 4 gram potassium carbonate (first ^ 16.5 ml water) and 0.49 g of tetrakis(triphenylene), reflux reaction 4 small Γ to room temperature: pour ί liquid into the water to stir the solids, transition ^ ancient ^, dry 'toluene recrystallize, cool, transition Take a solid, for dry, and pay 4.71 g of finished product with a purity of 99.25% and a yield of 58%. The purity of the product after sublimation is 99.6%. , melting point · · catching ~ point: (10) 宂 [HPLC conditions] column: (four), flow rate: U) m 100%
加碰(4GGMHZ)光譜數據:δ 8 队8 G9 (m,2H),7 82 7 95 (m, 9H), 7.58-7.76 (m, 5H), 7.41-7.56 (m, 6H), 7.30-7.35 (m, 4H), 7.16-7.25 (m, 4H)Adding touch (4GGMHZ) spectral data: δ 8 team 8 G9 (m, 2H), 7 82 7 95 (m, 9H), 7.58-7.76 (m, 5H), 7.41-7.56 (m, 6H), 7.30-7.35 (m, 4H), 7.16-7.25 (m, 4H)
[HPLC條件]官柱,流速:j 〇㈣分鐘⑶3Cn : 100% 純度99.5%。 20 200846441 !H NMR (400MHz)光譜數據:δ 8·05-8·09 (m,2H),8.01-8.03 (d,1Η),7·80-7·93 (m,11Η),7·58-7·76 (m,4Ή),7·41·7·54 (m, 6H),7.32-7:35 (m,2H),7·14-7·25 (m,4H) 比較例:先前技術之螢光主發光艟材料的製備 9-萘_2-基-10_『1,1’;4’,1’’1聯三茉-3-某-蔥(^11-1)之合成[HPLC conditions] column, flow rate: j 〇 (four) minutes (3) 3Cn: 100% purity 99.5%. 20 200846441 !H NMR (400MHz) spectral data: δ 8·05-8·09 (m, 2H), 8.01-8.03 (d, 1Η), 7·80-7·93 (m, 11Η), 7·58 -7·76 (m, 4Ή), 7·41·7·54 (m, 6H), 7.32-7:35 (m, 2H), 7·14-7·25 (m, 4H) Comparative example: Previous Preparation of Fluorescent Main Luminescent Material of Technology 9-Naphthalene_2-yl-10_"1,1';4',1''1,3,3,3,3-onion (^11-1)
在氮氣下置入3.1克3’,-溴-[1,Γ; 4,,1,,]聯三苯、5.0克 9-棚酸-10·萘-2-基-蒽、60 ml四氫吱喃、3.3克碳酸卸(先 溶於10 ml水)和〇·34克四(三苯基膦)鈀,迴流反應4小時, 冷卻至室溫,將反應液倒入水中攪拌逼出固體,過濾取固 體,烘乾,以曱苯再結晶,冷卻,過濾,取固體,烘乾,得 成品4·1克,純度99.1%,收率77.0%。產品昇華純化後純 度 99.6%。溶點:322.6。(:,Tg 點·· 124.8Χ。 [HPLC 條件]管柱:RP_8,流速·· 1.〇 ml/分鐘,CH3CN : H20=95 : 5 4 NMR (400MHz)光譜數據:δ 8·00-8·08 (m,2H),7.90-7.98 (m,2H),7.77-7.86 (m,7H),7.57-7·73 (m,9H),7.42-7.51 (m, 3H),7·28-7·37(πι5 5H) 實施例2·發光裝置測試資料 本實施例測試之裝置其結構包含1)玻璃基板、2)ΙΤΌ、 3)電洞注入層(HIL)、4)電洞傳輸層(HTL)、5)發光層(包 21 200846441 含螢光主發光體材料與螢光摻雜物)、6)電子傳輸層和7)陰 極。其中陰極係由0.7 nm的LiF和150 nm的A1所構成。 以真空蒸鍍方式來製備如第一圖所示之有機電激發光 元件,其中比較例的藍光主發光體材料為ADN和BH-1, 螢光掺雜物係為BD-1 (TBPE)與BD-2,其化學結構分別 如下:Under nitrogen, 3.1 g of 3',-bromo-[1,Γ; 4,1,]-triphenyl, 5.0 g of 9-butyric acid-10·naphthalen-2-yl-indole, 60 ml of tetrahydrogen were placed.吱 、, 3.3 g of carbonic acid unpacked (dissolved first in 10 ml of water) and 〇·34 g of tetrakis(triphenylphosphine)palladium, refluxed for 4 hours, cooled to room temperature, and poured into water to stir to solidify. The solid was collected by filtration, dried, recrystallized with benzene, cooled, filtered, solid, and dried to obtain 4·1 g of the finished product, purity 99.1%, yield 77.0%. The product was sublimed and purified to a purity of 99.6%. Melting point: 322.6. (:, Tg point··124.8Χ. [HPLC conditions] column: RP_8, flow rate·· 1.〇ml/min, CH3CN: H20=95: 5 4 NMR (400MHz) Spectral data: δ 8·00-8 · 08 (m, 2H), 7.90-7.98 (m, 2H), 7.77-7.86 (m, 7H), 7.57-7·73 (m, 9H), 7.42-7.51 (m, 3H), 7·28- 7·37(πι5 5H) Example 2·Light-emitting device test data The device tested in this example has a structure including 1) a glass substrate, 2) ΙΤΌ, 3) a hole injection layer (HIL), and 4) a hole transport layer ( HTL), 5) luminescent layer (package 21 200846441 containing fluorescent main illuminant material and fluorescent dopant), 6) electron transport layer and 7) cathode. The cathode system consists of 0.7 nm LiF and 150 nm A1. The organic electroluminescent device as shown in the first figure was prepared by vacuum evaporation, wherein the blue light main emitter material of the comparative example was ADN and BH-1, and the fluorescent dopant system was BD-1 (TBPE) and The chemical structure of BD-2 is as follows:
f BD-2 前述有機電激發光元件中電洞注入層、電洞傳輸層、 發光層和電子傳輸層之成分及厚度、以及其所組成之元件 的測試結果列於下表1 : 22 200846441 功率效率# 2.19 2.14 2.17 L84 1.74 1.47 3.96 3.70 3.84 3.37 3.03 y—< m 發光效率# 4.26 4.10 4.16 3,62 3.22 2.91 8.55 8.00 8.30 7.28 6,55 6.77 CIE* (0.14, 0.15) (0·14,0·15) (0·14, 0·15) (0.14, 0.15) (0.14, 0.16) 1(0.14,0,7) (0.15, 0.17) (0.15, 0.16) (0.15, 0.16) (0.15,0.16) (0.15, 0.18) (0.15,0.18) 電子傳輸層 (20 nm) Alq3 Alq3 Alq3 Alq3 丨 Alq3 1 i Alq3 Alq3 Alq3 Alq3 Alq3 Alq3 Alq3 發光層(25nm) 螢光 摻雜物 BD-1 BD-1 BD-1 BD-1 | BD-1 BD-1 BD-2 BD-2 BD-2 BD-2 BD-2 BD-2 主發光體 材料 Inv-1 Inv-2 Inv-3 Inv-4 ADN BH-1 Inv-1 Inv-2 Inv-3 Inv-4 ADN BH-1 電洞傳輸層 (20 nm) NPB NPB NPB NPB i NPB NPB NPB NPB NPB NPB NPB NPB 電洞注入層 (60 nm) CuPC CuPC CuPC CuPC CuPC CuPC CuPC CuPC CuPC CuPC CuPC CuPC 實施例1 實施例2 實施例3 -1 實施例4 I 比較例1 比較例2 實施例5 實施例6 實施例7 實施例8 比較例3 比較例4f BD-2 The composition and thickness of the hole injection layer, the hole transport layer, the light-emitting layer and the electron transport layer in the above-mentioned organic electroluminescent device, and the test results of the components thereof are listed in Table 1 below: 22 200846441 Power Efficiency # 2.19 2.14 2.17 L84 1.74 1.47 3.96 3.70 3.84 3.37 3.03 y—< m luminous efficiency # 4.26 4.10 4.16 3,62 3.22 2.91 8.55 8.00 8.30 7.28 6,55 6.77 CIE* (0.14, 0.15) (0·14,0 ·15) (0·14, 0·15) (0.14, 0.15) (0.14, 0.16) 1(0.14,0,7) (0.15, 0.17) (0.15, 0.16) (0.15, 0.16) (0.15, 0.16) (0.15, 0.18) (0.15, 0.18) Electron transport layer (20 nm) Alq3 Alq3 Alq3 Alq3 丨Alq3 1 i Alq3 Alq3 Alq3 Alq3 Alq3 Alq3 Alq3 Luminescent layer (25 nm) Fluorescent dopant BD-1 BD-1 BD- 1 BD-1 | BD-1 BD-1 BD-2 BD-2 BD-2 BD-2 BD-2 BD-2 Main illuminant material Inv-1 Inv-2 Inv-3 Inv-4 ADN BH-1 Inv -1 Inv-2 Inv-3 Inv-4 ADN BH-1 Hole Transport Layer (20 nm) NPB NPB NPB NPB i NPB NPB NPB NPB NPB NPB NPB NPB Hole Injection Layer (60 nm) CuPC CuPC CuPC CuPC CuPC CuPC CuPC CuPC CuPC CuPC CuPC CuPC Example 1 Example 2 Example 3-1 Example 4 I Comparative Example 1 Comparative Example 2 Example 5 Example 6 Example 7 Example 8 Comparative Example 3 Comparative Example 4
e(N 迴 #Μ^^Νδο/νε 03蛘, 200846441 由上表可知’不論在以BD_1或BD_2深藍色螢光掺雜 物之組別比較中,本發明之深藍色主發光體材料(hvd、 InV-2、InV-3、Inv-4)都具有優於先前技術之深藍色主 體材,(AND、BH-1)之發光效率及功率效率。 第二圖為本發明之ϊην]的孔光譜圖,其波峰位於412 nm和/32細處,進一步取^丨之孔光譜圖與先前技術 二監發ϊ體材料ADN、BH_1進行pl絕對強度之疊 ’由於本發明1Μ 1的結構導入了立體 相較^下明顯。,故Μ之榮光頻譜與ADN和BH·1 由於T !:監夕。此外,依照據F6rSter能量轉移機制, 使^ Μ· j BD·2之頻譜的重疊面積較大,故在發光層中 使用^^咖2時’其發光效率會有顯著的提昇。 «^ ;.Ιην'2'Ιην-3 ^lnv-4 ^ ^ ^ 絕對強;^ T 巴對強度圖’其中¥軸係正規化後的 PL X2 ; 'Γ:3 ^ InV"4 收絕對強度。由圖可知二;二„表其,及 之螢光样光故在發光射使用本發明 提昇。發総料配合BD_2時,其發光效率會有顯著的 uv 和BH_1之1^絕對強度圖與BD]之 在ADN和BH ^中Y軸係正規化後的絕對強度值, 吸收絕對強声,由^表PL絕對強度,在BD-1則代表UV 與螢光摻雜itηη_9θ可知,先前技術之螢光主發光體材料 發光體材料之重疊譜重疊狀況並未如本發明之螢光主 —圖為 Inv-1、Inv_2、Inv 3、inv 4、adn 和 bh i 24 200846441 分別掺雜抓1 (TBPE)戶斤得之電流密度/發光效率圖。在 相同的電流密度下,本發明之肇光主發光體材料㈤心、 I:2、Inv_3、Inv_4)皆具有’相較於先前技術之營光主發光 體材料較高的發光效率。 f-b® ^lnv-l; Inv-2 . Inv_3 ^ Inv.4 )所付之電激發光頻譜,由圖顯示發光層中且有本 紐材料與螢光摻雜物BD·1之有機Ϊ激發 先裝置係可發出藍光。 第八圖為Inv-卜 Inv_2、Inv_3和Inv_4之pL絕 =声 強度圖,其中¥軸係正規化後: ’在BD-2則代表UV吸收絕對強度。雖然本發明之 ,,發光體材料與BD-2之頻譜重疊狀況不如肋_卜但 5於第三圖所示,仍呈現優於先前技術之螢光主發光體 八 ί A ^ ^ ImM ' InV_2 ' InV_3 ' Inv·4、ADN 和 BH-1 二3 所得之電流密度/發光效率圖,在相同的電 山ί下,本發明之化合物有較高的發光效率。 所/ t 圖為 ImM、InV_2、InV_3 和 InV·4 分別掺雜 BD-2 主‘光η光頻譜由圖顯示發光層中具有本發明之螢光 發出4材料與$光摻雜物肋·1之有機電激發光I置係可 升螢光^1 ί明之螢絲發光體抱係具有可提 =雜物之發光效率及壽命、以及易於合 本發明之有機電激發光裝置能夠發出深藍色光,且 异有鬲發光效率。 25 200846441 其他實施態樣 在本說明書中所揭露的所有特徵都可能與其他方法結 合,本說明書中所揭露的每一個特徵都可能選擇性的以相 同、相等或相似目的特徵所取代,因此,除了特別顯著的 特徵之外,所有的本說明書所揭露的特徵僅是相等或相似 特徵中的一個例子。 雖然本發明已以較佳實施例揭露如上,然其並非用以 限定本發明,任何熟悉此技藝者,在不脫離本發明之精神 和範圍内,當可作各種之更動與潤飾。 26 200846441 【圖式簡單說明】 第一圖為有機電激發光裝置的示意圖。 第二圖為Inv-l之PL光譜圖。 第三圖為Inv]、ADN、BH4之pL絕對強度 之UV吸收絕對強度圖。 、_ 第四圖為 Ιην·1、Ιην_2、ιην_3 和 hv-4 之 ρτ 你 圖與BD_i之UV吸收絕對強度圖。 %對強度 第五圖為ADN和BH-1之PL絕對強度圖邀, UV吸收絕對強度圖。 ,、ΒΙΜ之 弟 /、圖為 Ιην·1、Inv-2、Inv-3、Inv-4、AD]si 1 分別f雜ΒΙΜ (ΤΒΡΕ)所得之電流密度/發光欵率^ΒΗ·1 (TrI七、圖為 InV_1、InV·2、Μ·3 和 InV_4 分別掺^ BD-1 ^ βΡΕ)所得之電激發光頻譜。 第八圖為 Inv-1、Inv_2、Inv_3 和 Inv-4 之 妨 μ , 一 圖盥> ττ ^絶對強度 口 /、之UV吸收絕對強度圖。 弟九圖為 Inv-1、Inv-2、Inv-3、Inv-4、AC)Kr t /> -λ N 和 BH-1 刀乃』谬雜BD-2所得之電流密度/發光效率圖。 第十圖為Inv-1、Inv-2、Inv-3和Inv-4分別执^ 所得之電激發光頻譜。 >雜购 【主要元件符號說明 無 27e(N回#Μ^^Νδο/νε 03蛘, 200846441 It can be seen from the above table that the dark blue main illuminant material of the present invention (hvd) is in comparison with the group of BD_1 or BD_2 dark blue fluorescent dopants. , InV-2, InV-3, Inv-4) have higher luminous efficiency and power efficiency than the deep blue main materials of the prior art, (AND, BH-1). The second figure is the hole of ϊην] of the present invention. The spectrum of the spectrum is located at 412 nm and /32, and further the spectrum of the pores of the pores is combined with the precursors of the precursors ADN and BH_1 for the absolute intensity of pl. The stereoscopic phase is more obvious than that of ^. Therefore, the glory spectrum of Ao and BH·1 is due to T!: 夕夕. In addition, according to the F6rSter energy transfer mechanism, the overlapping area of the spectrum of ^ Μ· j BD·2 is larger. Therefore, when using ^^咖2 in the luminescent layer, its luminous efficiency will be significantly improved. «^ ;.Ιην'2'Ιην-3 ^lnv-4 ^ ^ ^ Absolutely strong; ^ T Bar versus intensity graph' Among them, the ¥ axis is normalized after PL X2; 'Γ:3 ^ InV"4 is the absolute intensity. It can be seen from the figure; the second is the table, and the fluorescent light is emitted. The invention uses the present invention to improve the luminous intensity of the uv_2 and the hull 配合2, and the absolute intensity values of the uv and BH_1 absolute intensity maps and BD] in the ADN and BH^ y-axis normalization, Absorptive absolute sound, by absolute intensity of PL, and BD-1 represents UV and fluorescent doping itηη_9θ. It is known that the overlap spectrum of the prior art fluorescent main emitter material emitter material is not as in the present invention. Fluorescent main - the picture shows the current density / luminous efficiency diagram of Inv-1, Inv_2, Inv 3, inv 4, adn and bh i 24 200846441 respectively doped 1 (TBPE) households. At the same current density, The neon light-emitting material of the present invention (5), I: 2, Inv_3, Inv_4) has a higher luminous efficiency than that of the prior art camping main illuminant material. fb® ^lnv-l; Inv- 2. Inv_3 ^ Inv.4 ) The spectrum of the electro-excitation light emitted by the Inv_3 ^ Inv.4 ) is shown in the figure. The organic device of the luminescent layer and the fluorescent dopant BD·1 can emit blue light. For the Inv-Bu Inv_2, Inv_3, and Inv_4 pL absolute = sound intensity map, where the ¥ axis is normalized: 'In BD-2 generation The table UV absorbs the absolute intensity. Although the present invention, the spectrum overlap of the illuminant material and the BD-2 is not as good as that of the ribs, but it is superior to the prior art fluorescent main illuminator. The current density/luminescence efficiency graph obtained by A ^ ^ ImM ' InV_2 ' InV_3 ' Inv·4, ADN and BH-1 2-3, the compound of the present invention has a higher luminous efficiency under the same electric charge. The /t picture is ImM, InV_2, InV_3, and InV·4, respectively, doped with BD-2 main 'light η light spectrum. The figure shows that the luminescent layer of the present invention has the luminescent emission 4 material and the light dopant rib·1 The organic electroluminescence excitation light I can be used to raise the fluorescent light. The illuminating filament illuminator has the luminous efficiency and the lifetime of the debris, and the organic electroluminescent device which is easy to incorporate the present invention can emit deep blue light. And different 鬲 luminous efficiency. 25 200846441 Other Embodiments All of the features disclosed in this specification may be combined with other methods, and each of the features disclosed in this specification may be selectively replaced with the same, equal or similar purpose features, thus In addition to the particularly salient features, all of the features disclosed in this specification are only one of the equivalent or similar features. While the invention has been described above in terms of the preferred embodiments thereof, it is not intended to limit the invention, and various modifications and changes can be made without departing from the spirit and scope of the invention. 26 200846441 [Simple description of the diagram] The first diagram is a schematic diagram of an organic electroluminescent device. The second picture is the PL spectrum of Inv-1. The third graph is the absolute intensity of UV absorption of the absolute intensity of pL of Inv], ADN, and BH4. _ The fourth figure is the ρτ of Ιην·1, Ιην_2, ιην_3, and hv-4. The absolute absorption of UV absorption of the graph and BD_i. % versus intensity The fifth figure shows the absolute intensity map of the PL and the absolute intensity of the UV absorption of ADN and BH-1. , ,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,,, 7. The graph shows the spectrum of the electrical excitation light obtained by injecting BD-1^βΡΕ into InV_1, InV·2, Μ·3, and InV_4, respectively. The eighth figure is the absolute intensity map of Inv-1, Inv_2, Inv_3, and Inv-4 μ, a graph 盥> ττ ^ absolute intensity port /, UV absorption. The nine figures are the current density/luminescence efficiency of Inv-1, Inv-2, Inv-3, Inv-4, AC)Kr t /> -λ N and BH-1 Knife 谬 BD-2 . The tenth figure shows the spectrum of the electroluminescence obtained by Inv-1, Inv-2, Inv-3 and Inv-4, respectively. >Miscellaneous purchase [Main component symbol description None 27
Claims (1)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| TW096117650A TW200846441A (en) | 2007-05-17 | 2007-05-17 | Fluorescence main host material and organic electroluminescence device using the material |
| KR1020070076555A KR100895195B1 (en) | 2007-05-17 | 2007-07-30 | Host material and organic electroluminescent device using the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| TW096117650A TW200846441A (en) | 2007-05-17 | 2007-05-17 | Fluorescence main host material and organic electroluminescence device using the material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200846441A true TW200846441A (en) | 2008-12-01 |
| TWI343411B TWI343411B (en) | 2011-06-11 |
Family
ID=40287850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW096117650A TW200846441A (en) | 2007-05-17 | 2007-05-17 | Fluorescence main host material and organic electroluminescence device using the material |
Country Status (2)
| Country | Link |
|---|---|
| KR (1) | KR100895195B1 (en) |
| TW (1) | TW200846441A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2725031A4 (en) * | 2011-06-25 | 2014-12-03 | Xuanzhu Pharma Co Ltd | DERIVATIVES OF C-GLYCOSIDES |
| US9315438B2 (en) | 2014-01-03 | 2016-04-19 | Xuanzhu Pharma Co., Ltd | Optically pure benzyl-4-chlorophenyl-C-glucoside derivative |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3148176B2 (en) | 1998-04-15 | 2001-03-19 | 日本電気株式会社 | Organic electroluminescence device |
| US7195829B2 (en) * | 2004-03-30 | 2007-03-27 | Eastman Kodak Company | Organic element for electroluminescent devices |
| KR100786292B1 (en) * | 2005-07-15 | 2007-12-18 | 삼성에스디아이 주식회사 | Organic electroluminescent element |
-
2007
- 2007-05-17 TW TW096117650A patent/TW200846441A/en not_active IP Right Cessation
- 2007-07-30 KR KR1020070076555A patent/KR100895195B1/en not_active Expired - Fee Related
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2725031A4 (en) * | 2011-06-25 | 2014-12-03 | Xuanzhu Pharma Co Ltd | DERIVATIVES OF C-GLYCOSIDES |
| US9562029B2 (en) | 2011-06-25 | 2017-02-07 | Xuanzhu Pharma Co., Ltd. | C-glycoside derivatives |
| US10253010B2 (en) | 2011-06-25 | 2019-04-09 | Sihuan Pharmaceutical Holdings Group Ltd. | C-glycoside derivative |
| US9315438B2 (en) | 2014-01-03 | 2016-04-19 | Xuanzhu Pharma Co., Ltd | Optically pure benzyl-4-chlorophenyl-C-glucoside derivative |
| US9914688B2 (en) | 2014-01-03 | 2018-03-13 | Sihuan Pharmaceutical Holdings Group Ltd. | Optically pure benzyl-4-chlorophenyl-C-glucoside derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| TWI343411B (en) | 2011-06-11 |
| KR20080101619A (en) | 2008-11-21 |
| KR100895195B1 (en) | 2009-04-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Shih et al. | A Novel Fluorene‐Triphenylamine Hybrid That is a Highly Efficient Host Material for Blue‐, Green‐, and Red‐Light‐Emitting Electrophosphorescent Devices | |
| Hsu et al. | Phosphine-oxide-containing bipolar host material for blue electrophosphorescent devices | |
| TWI377867B (en) | ||
| TWI585091B (en) | Organic electroluminescent elements | |
| TWI356090B (en) | Organic electroluminescent element | |
| JP5781499B2 (en) | Novel organic electroluminescent compound and organic electroluminescent device using the same | |
| JP5998234B2 (en) | Composition | |
| CN101918370B (en) | Compound for organic electroluminescent device and organic electroluminescent device using same | |
| Liu et al. | Deep-blue fluorescent emitter based on a 9, 9-dioctylfluorene bridge with a hybridized local and charge-transfer excited state for organic light-emitting devices with EQE exceeding 8% | |
| CN101506328B (en) | Organic electroluminescent device material and organic electroluminescent device | |
| TW201006908A (en) | Compound for organic electric field light-emitting element and organic electric field light-emitting element | |
| CN102633820A (en) | Compound for organic electroluminescent element and organic electroluminescent element | |
| TW201035280A (en) | Novel compound for organic photoelectric device and organic photoelectric device including the same | |
| JP2009269909A (en) | New compound for electronic material and organic electronic device using the same | |
| Shi et al. | A simple D–π–A hybrid mode for highly efficient non-doped true blue OLEDs with CIE y< 0.05 and EQE up to 6% | |
| Zhang et al. | Planarized intramolecular charge transfer on triphenylamine-modified pyrazine and its application in organic light-emitting diodes | |
| Jia et al. | Achieving non-doped deep-blue OLEDs by applying bipolar imidazole derivatives | |
| JP2019172608A (en) | 1,3,5-triazine compound, composition containing the compound, organic electroluminescent element, display device, and luminaire | |
| Liu et al. | Isomeric thermally activated delayed fluorescence emitters based on a quinolino [3, 2, 1-de] acridine-5, 9-dione multiple resonance core and carbazole substituent | |
| Liu et al. | Efficient Non‐doped Blue Fluorescent Organic Light‐Emitting Diodes Based on Anthracene–Triphenylethylene Derivatives | |
| Zhan et al. | A High‐Efficiency Ultraviolet Organic Light‐Emitting Diode Employing a Double Boron–Oxygen–Nitrogen‐Based Emitter | |
| Peng et al. | High performance deep-blue organic light emitting diodes via excited state regulation of phenanthroimidazole-triazole derivatives | |
| Wang et al. | Rational molecular design of phenanthroimidazole-based fluorescent materials toward high-efficiency deep-blue OLEDs by molecular isomer engineering | |
| Li et al. | High-efficiency green organic light-emitting devices with low efficiency roll-off using π-shape materials as host | |
| JP2007254737A (en) | Organometallic complex for organic light-emitting layer and organic light-emitting diode |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |