TW200914401A - Synthesis of triphenylene and pyrene based aromatics and their application in OLEDs - Google Patents

Abstract

The present invention provides a compound of general formula (I) Ar1-R1-Ar2 wherein Ar1 and Ar2 independently represent triphenylenyl or pyrenyl, and R1 represents one bond, aryl or heteroaryl. The present invention provides not only a process for the preparation of the compound of formula (I), but also an organic electroluminescence device which is characterized by the compound of formula (I) being a luminescent material.

Description

200914401 IX. Description of the Invention: [Technical Field] The present invention relates to a novel compound which has good thermal stability and good efficiency and is suitable as a luminescent material on an organic electroluminescent device, especially one Luminescent material in the blue to green wavelength range. [Prior Art] The origin of Organic Electroluminescence can be traced back to 1963. When Pope1 et al. studied the thickness of a single crystal with a thickness of 1〇~2〇μιη, it was first discovered that after applying a high voltage across the crystal. It can be observed that blue fluorescence 'steps out of the study of organic electroluminescence; but it is difficult to grow large-area single crystal, and the required driving voltage is too high, and the luminous efficiency is higher. Inorganic materials are poor and therefore have no practical value. Until 1987, the Eastman Kodak company's Tang and VanSlyke2 used new component process technology, using vacuum hot-salt Amorphous technology, and innovative heterojunction (Heter0juncti〇) n) The production of a multilayer organic film (Multilayer) containing electrons and a hole transport layer is a breakthrough. They use aromatic diamine (TAPC) as the material of the hole transport layer, and the film-forming properties of 叁 (8_ hydroxy 啥 吕 吕 (10) (four) sand (four) called domain (10) coffee - called (1)), butterfly 3) as the electron transport layer and luminescent materials A vacuum crucible method (ν_·vapor deposition) is used to make a thin crucible of 60 to 70 nm, and a silver alloy with a low work function is used as a cathode to improve the injection efficiency of electrons and holes. Its two-layered one-piece structure, the electron and the hole are recombined on the p_n surface (Rec — ) to release light. It produces a wavelength of (four) coffee

123313.DOC 200914401's green light 'has low driving voltage (<10 v), high quantum efficiency (> ι and not =: part stability' greatly enhances the properties and compatibility of organic small molecule electroluminescent elements At this point, organic electro-optic display technology has gradually been valued 'and then caused a wave of research. - On the other hand, the first component with an organic polymer as a light-emitting layer was in 1990 by Cambridge University. Burroughes et al. 3 of Calvendish Laboratories, Inc., to make a single-layer organic film by solution spin coating Q (SP111 C〇atlng), and to use poly(p-phenylene viny丨ene), PPV As an illuminating layer, an electroluminescent device is produced. Due to its simple process, good polymer properties and semiconductor-like properties, the research on conjugated luminescent materials has been rapidly developed, which has led to another wave study. Second, many organic polymers also have high-efficiency luminescence properties. The principle of organic electroluminescence involves the injection and transport of carriers. Recombination is used to form (j excitons). Common organic electroluminescent elements include an anode, a Hole Transporting Layer (HTL), and an Emitting Layer (EML). Electron transport layer (Electron transporting (layer, ETL), a cathode. In terms of materials: First, the anode electrode is: a horse work function and transparent indium tin oxide (ITO) 'hole transport layer The material may be hydrazine, Ν·-diphenyl-N,N'-bis(3-methylphenylbiphenyl-4,4'-diamine (1^,^['-(11卩11611丫1- 1'4,1^'-1^-(3-methylphenyl)-l,l'biphenyl-4,4'-diamine,TPD) or N,N,-diphenyl-N,N'-double (1 -naphthylbiphenyl-4,4'-diamine (N,N'-bis-phenyi-

123313.DOC 200914401 N'N-bis-( 1-naphthyl)-1,r-biphenyl-4,4'-diamine,NPB) » The electron transport layer material can be Alq and 2-2,-2"-(l ,3,5·benzenetriyl)叁_(i_phenyl-1-hydro-benzimidazole)(2_2,_2,,_(丨,3,5_benzenetriy丨)tris_〇_ phenyl-l-H_benzimU daz 〇le), τρΒΙ), metals commonly used in cathodes such as low work function calcium (Ca), magnesium silver alloy (Mg: Ag aU〇y), aluminum and lithium fluoride or lithium alloys (LiF/Al, Li/ ΑΙ). Next, the hole transport layer, the light-emitting layer, and the electron transport layer are sequentially formed into a film by vacuum evaporation, and then the cathode is plated. when! When the energy barrier of the T0 electrode and the hole transport layer is too large, there is a difficulty in hole injection and a low hole transfer efficiency. Therefore, it is necessary to add a hole injection material between them to reduce the ITO electrode and The energy barrier between the interface of the hole transport layer enables the hole to be smoothly injected from the ITO electrode into the hole transport layer. Common hole injection materials such as copper phthalocyanine (CuPc) 4 and poly(3, dioxyethyl) Benzene): Poly(3,4-ethylenedioxythiophene): poly(styrene sulfonate), PEDOT:PSS). (J) When the electrodes at both ends of the device are positively biased, electrons are injected from the cathode into the lower unfilled rail region (LUMO) of the electron transport layer, and the holes are injected from the anode into the highest fill rail of the hole transport layer. In the domain (HOMO), under the drive of an applied electric field, the hole moves toward the cathode, and the electron moves toward the anode. Finally, the hole and electrons recombine in the luminescent layer to form excitons, and then the excitons are deactivated. If a hole blocking layer is added between the light-emitting layer and the electron-transporting layer, too many holes can be blocked from running to the cathode electrode to prevent the holes and electrons from canceling each other. Research on small-molecule blue light materials, Tsinghua University Dr. Yu Ting 5 Li

I23313.DOC 200914401 The use of epitaxial metal complexes to catalyze the dimerization of epoxides to successfully synthesize blue luminescent materials with high melting point and efficiency: double-stranded benzene (2, 2) , -biStriphenylene, BTP). When the component is ITO/TPD/BTP/TPBI/Mg: Ag has the best efficiency, the light-emitting position is 458: nm, the external light-emitting efficiency is as high as 4.2%, the current luminance efficiency is 4.0 Cd/A, and the energy efficiency is 2.5 lm/ W, the starting voltage is 3.5 V, the maximum brightness is 2 1 204 cd/m2 'and the half-wave width is only 72 nm, and the illuminance chromaticity coordinate cie is maintained at (0.14, 0.11), which is hardly affected by the applied voltage. 〇^. In addition to the above BTP, Tsinghua University Wu Guofan 6 and Dr. Gu Boren 7 have also developed a blue luminescent material based on Pyrene. They have synthesized nine derivatives, among which the best performing derivatives. U4_bisindenyl 2,5_decyloxy-benzene (P2)' has a glass transition temperature (Tg) of i33 °c, and emits light when the element structure is ITO/TPD/P2/TPBI/Mg:Ag The position is 488 nm, the starting voltage is only 3 V, and the external light emission efficiency exceeds the theoretical limit of the fluorescent element by up to 6.1%. 'The size of the large-scale shell is also rushed to 74,590 cd/m2, and the current brightness efficiency is reduced to 12 · 6 cd/A. The energy efficiency is 6 · 7 1 m / W, and the CIE is (0.15, 0.2 8) 'is a relatively light blue color. In 2004, Professor Zhang Genwei and Professor Wu Zhongzhi from the National Taiwan University jointly published the blue light material of the 叁(9,9-diaryif丨u〇rene)s (Ter(9,9_diaryif丨u〇rene)s, : TDAFs). The type of spiral (spir〇_) structure is very good because of the strong bond strength of c邛3_Csp2, and the film is highly resistant to heat. When the component IT〇/PED〇T:pss/TDAFl/TpBi/UF/A1 is called 'Where TDAF1 is a derivative of the volume (9,9-bisaryl fluorene), the starting voltage is about 2.5 volts, and the current brightness efficiency is 1.53 cd/A, maximum brightness

123313.DOC 200914401 about 14000 cd/m2, CIE is (0.16, 0.04) 'Although the external quantum efficiency is as high as 5.3%, it is a pity that TDAF1 is just in the series of three (9,9-bisaryl fluorene) derivatives. There is no one of the glass transition temperatures (Tg). Professor Xu Qingfeng of Jiaotong University and Professor Tao Yutai of the Academia Sinica jointly published a modification from 4,4'-bis(2,2-distyrylbiphenyl) (2,4,_bis (2,2) -diphenylvinyl)-l,l'-biphenyl,DPVBi) 2,7-bis(2,2, one ethylene)-9,9'-helix (2,7-1^5 (2,2) - €11 1161171\^11丫1)9,9'-spirobifluorene, DPVSBF) 9. The main change is to change the original biphenyl to spirobifluorene and convert the glass to temperature (Tg). The increase from 64 C to 11 5 °C 'has greatly improved the thermal stability of the film. When the component structure is ITO/NPB/DPVSBF/Alq/LiF/Al, the brightness position is 474 nm' and the external light emission efficiency is 3.03. %, the maximum brightness is 41247 cd/m2 'At the same time, the current brightness efficiency is 5.33 cd/A, the energy efficiency is 4.76 1 〇 1 / take, (: 1 £ is (0.16, 0.24), not only the component efficiency and brightness ratio DPVBi Goodly, the operating life is also 16 times higher than that of DPVBi. Professor Li Shutang of the City University of Hong Kong also published the blue material 10 of Pyrene and Fluorene in 2005. These 2,7-two masks Base _ 9,9'-dimercapto-anthracene (2 , 7-dipyrenyl-9,9,-dimethyNfluorene, DPF) Derivatives have a fairly high glass transition temperature (Tg), ranging from ^45 ^ to 193 C, which is best performed by DPF after the component is fabricated. When the structure is ITO/CUPC/NPB/DPF/TPBI/LiF/Mg:Ag, the light emission position is 469 nm. The current brightness efficiency is 5.3 cd/A, the energy efficiency is 3.〇im/w, and the maximum brightness is about 9260 cd. /m2, CIE is (0.16, 0.22). From the above literature, let us know that instead of increasing the benzene ring (increasing the total I233I3.DOC -10- 200914401 units), the material can be better after the components are made. The efficiency of 'but steric hindrance, can indeed improve the glass transition temperature (Tg). Related to the study of triphenylene derivatives on blue light elements, the inventor has a good The result, but the derivative has no glass-conversion temperature (Tg), which is always a disadvantage in terms of thermal stability. After research, it was found; the agricultural part of the bamboo has a good glass transition temperature (Tg). The same leaf ash itself also has good fluorescence efficiency (Quinine Sulfate EquiValent (Q.E.): 71%), an anthracene derivative that changes the number of intermediate benzene rings will have an opportunity to improve and enhance the efficiency of the element. In addition, the wavelength of the emission can be changed by changing the conjugate.

Sato has proposed that in the improvement of hole transport materials, the group having more 7 Γ electrons and the heavy atom molecule which can reduce the spin torque can improve the glass transition temperature. (Tg)ll. Professor Shir〇ta has pointed out that 12's addition of rigid bismuth (Fiuorene) can also increase the temperature of glass to U, but too much thiophene will cause red shift of the material's luminescence. The Wang Genyi research team of National Taiwan University also published in 2002. Using the 4 olefin's oligothiophenes as the core ruthenium derivative η, the number of thiophenes in the center can be changed to make the whole molecule emit light from light blue to bright yellow, which echoes in this respect. Results published by Professor Shirota 2' Another important point in this literature is that the glass transition temperatures (Tg) of these materials are fairly stable, both at 153 to 154 °C, and are not subject to the number of τ»Thiophenes. Increase or decrease and influence. Looking for an organic electroluminescent material in the blue to green wavelength range

123313.DOC 200914401 It is important to make the luminescent material have good thermal stability and good efficiency in the performance of the component. Accordingly, in the present invention, an asymmetric derivative of ruthenium and ruthenium benzene is synthesized as a luminescent material for an organic electroluminescent device. References: 1. P. Pope, Η. P. Kallmann, P. Magnante, J. Chem. Phys. 1963, 38, 2042. 2. CW Tang, SA VanSlyke, Appl. Phys. Lett. 1987, 51, o 913. 3. JH Burroughes, DDC Bradley, AR Brown, RN Marks, KD Mackay, RH Friend, PL Burn, AB Holmes, Nature 1990, 347, 539. 4. M. Era, C. Adachi, T. Tsutsui, S, Saito, Chem. Phys. Lett., 1999, 178, 488. 5. Η. T. Shih, CH Lin, YT Lin, CH Cheng, Adv. Mater. q 2002, 14, 1409. 6. Wu Guozhen, Suzuki Research on the reaction of organic electroluminescent diode materials, National Master's Thesis of Tsinghua University, Republic of China 91 years.: 7. Gu Boren, benzophenanthrene derivatives and anthracene derivatives in organic electroluminescent elements; , Ph.D. Thesis of National Tsinghua University, Republic of China, 1994. 8. CC Wu, KT Wang, YT Lin, Υ· Υ· Chien, Adv. Mater. 2004, 16, 61. 9. FI Wu, CF Shu, TT Wang, Li , CH Chien, YT Tao, Synth. Met. 2005, 151, 285. I233I3.DOC 12 200914401 10. S. Tao, Z. Peng. X. Zhang, CS Lee, ST Lee, Adv. Funct. Mater. 2005, 15, 1716. 11. Y. Sato, T. Ogata, M. Fugno, Proc. SPIE on Org. Light-emitting Mater. & Dev. II, 1999, 198, 3797. 12. Y. Shirota, K. Okumoto , H. Inada, Synth. Met. 2000, 111, 387. 13. KT Wong, CF Wang, CH Chou, Yuhlong Oliver Su, G.

H. Lee, Org. Lett. 2002, 4, 4439. SUMMARY OF THE INVENTION The object of the present invention is to provide a novel compound which can be used as a luminescent material for an organic electroluminescent device due to its good thermal stability and good The efficiency 'is therefore a good maximum brightness, optimum external quantum efficiency, optimum current efficiency and optimum energy efficiency value in the S piece performance. Another object of the present month is to provide a process for preparing the above compounds. A further object of the month is to provide an organic electroluminescent device comprising an anode, a hole transmission screen, a special fi, a material stop/seven layer, an electron transport layer, a cathode, and a layer of a luminescent material having the above compound. The present invention provides a novel compound of the following chemical formula (1):

Ar-R'-Ar2 ^ (I) wherein Ar丨 and Ar2 are a triple or a fluorenyl group, and R is a bond, a hydrazine or a aryl group. ~ Zhongfang Shenji is also replaced by one or more substituents, depending on the situation.

Ar1, eight factories and !^ can be independent

I23313.DOC 200914401 is preferably substituted with one, two, three or four substituents selected from the group consisting of a hydrogen atom, an atom of an atom (for example, fluorine 'gas, bromine, iodine); an aryl group, a gemin. An aryl group, a halogen-substituted arylalkyl group, an alkyl-substituted aryl group, a haloalkyl-substituted arylalkyl group or an aryl-substituted clC2 decyl group; an electron donating group such as a CNC 2 decyl group; (e.g., f-group, ethyl, butyl), C1_C20 cycloalkyl (e.g., cyclohexyl), C1-C20 alkoxy (Alkoxy gr0Up), C1-C20 substituted amino group (Amino group), having a substituent Aromatic amine groups (for example: Aniline); Electron withdrawing groups such as halogen, Nitrile, Nitro, Carbonyl, Cyano, CN) or a halogen-substituted C1-C20 alkyl group (for example: trimethylmethane, CF 3); a group consisting of heterocyclic substituent groups. The above aromatic groups may include, but are not limited to, phenyl, Naphthyl, Diphenyl, Anthryl, Pyrenyl, Phenanthryl and Diphenyl. And a five-ring (Fluorene) or other form of polyphenyl ring substituent biphenyl. The above-mentioned fragrant heterogeneous group may include, but is not limited to, Pyrane, Pyrrohne, Furan, Benzofuran, Thiophene, Benzene. Benzothiophene, Pyridine, Quin〇iine, is〇quin〇Hne. ratio. Pyrazine, Pyrimidine, Pyrrole,. Pyrazole, imidazole, indole, Sitting (Thiazole), different α嗤嗤 (is〇thiaz〇ie), σ恶哇(〇xaz〇ie), different. Isoxazole, benzopyrene. Sitting (Benzothiazole), benzo and squatting

I233I3.DOC -14- 200914401 (Benzoxazole), 1,2,4-trioxazole (1,2,4-Triazole), 1,2,3-trioxo (l,2,3-Triazole), two Milk and (phenanthroline) or other forms of heteronuclear aromatic rings. In a specific embodiment of the compound of the above formula (1), when Ari = Ar2, the ruler is an aromatic heterocyclic group. One of the compounds is specifically such that when R1 of the compound of the above formula (I) is a bond, the structural formula of the embodiment may be

(PT)

(PPT) When R1 of the compound of the above formula (I) is a biphenyl group, the other structural embodiment of the compound may be different from the structural formula of the specific embodiment of the present invention.

I23313.DOC -15- 200914401

When R1 of the compound of the above formula (I) is a 4-phenyl group, and ArLAr2 is a tri-phenylene group, the structural formula of another specific embodiment of the compound may be

Another structural embodiment of the compound may be

When R1 of the compound of the above formula (I) is pyrimenyl, and Ar1 is different from Ar2, another structural embodiment of the compound may have a structural formula of 123313.DOC 16 200914401

The invention further provides a process for the preparation of a compound of formula (i) above, which comprises

(a) when R1 is a bond, reacting a compound of the formula with a compound of formula (III) Ar2-Y to form a compound of formula (1); or

Ar1— R1—X1 + Ar2— γ Ar1— Rl— Ar2 "7 (11) (HI) (I) (b) When R1 is an aromatic or aromatic heterocyclic group, and Ar1 is different from Ar2 (The IUAr^RLxi compound is reacted with a compound of the formula (πι) Α 2 2 υ to form a compound of the formula (I); or (c) SR is an aryl group or an aromatic heterocyclic group, and when Arl=Ar2=linked triphenylene, the formula (iv) a compound is reacted with a compound of formula (v) x2_r1_x3 to form a compound of formula (I); or

Χ2, Κ丨1 x3 + Ar丨-Ri-Ar2 (V) (I) Fangtung heterogeneous group, when Ar1=Ar2=masking,

123313.DOC •1*7- 200914401 The compound of formula (III) Ar2-Y is reacted with a compound of formula (v)x2-r1_X3 to form a compound of formula (I);

Ar2- γ + X2 - R丨-X3 — Ar1 - R1- Ar2 (III) (V) (1) wherein X1, X2, X3 are a gas atom (Cl), a bromine atom (Br) or a substitution atom (I), y is Oxidation of alcohol (b(oh)2). In the above preparation method, the reaction in the steps (a), (b) and (d) is a 〇 Suzuki Coupling reaction, and the reaction in the step (C) is a Coupling reaction. It is generally known that the reaction conditions for the Suzuki Coupling reaction or the Coupling reaction can be applied to the process of the present invention. The compound of the formula (b) (π) αΡ-κΛχ1 can be formed by reacting a compound of the formula (IV) with a compound of the formula (V) X^Ri-X3.

The hole transport layer, the light-emitting layer, the electron transport layer, and the cathode are characterized in that the light-emitting layer is a light-emitting material having a compound of the formula (I). The following examples are intended to further illustrate the present invention, but are not intended to limit the scope of the present invention, and any one skilled in the art of the present invention, #明夕拉, i π 牙牙本本Modifications and variations are examples of the invention

123313.DOC -18- 200914401 Wai. EXAMPLES The above-described embodiments of the related inventions will be described in the following specific examples. Example 1 Synthesis of a compound of the formula (IV) (1,4-dihydro-l, 4-epoxytriphenylene) M 9-Bromophenathalene (25.7 g, 100 mmol) and sodium amide (11.7 g, 300 mmol) were placed in a vacuum exchange Nitrogen (500·6 g, 508 mmol) and anhydrous tetrahydrofuran (200 mL) were added to a 500 mL reaction flask of several times of nitrogen. The temperature was slowly raised to 65 °C and then reacted for 6 hours. Filtration to remove the salts. The solids after concentration under reduced pressure were purified on a silica gel column. The extract was ethyl acetate: hexane = 1 : 5, and the pale yellow solid was isolated after separation.

Synthesis of pyren-l-yl-l-boronic acid 1-Bromopyrene (2_0 g, 7.12 mmol) was dissolved in 1 mL of anhydrous tetrahydrofuran and 丨00 mL of anhydrous ether at -78 °C. In the nitrogen system, when the solution was stirred, n-butyllithium (4.9 ml, 7.83 mmol) was slowly added dropwise. At this time, the original yellowish transparent solution slowly turned into bright yellow opaque, and the system temperature was controlled at -78 C for 10 minutes. 1 min at -10 °C, then maintain _78 I23313.DOC • 19- 200914401 °C for 30 minutes' then slowly drip into tri-methyl borate (4.93 mL, 21.36 mmol) 'Stir at -78 °C for 30 minutes, It was observed that the solution turned into a transparent yellow orange color, and then warmed to 0 ° C for 3 hours, the solution turned yellow opaque, and then warmed to room temperature and stirred for 1.5 days. Then, 1 〇〇 mL, 1 〇% aqueous hydrochloric acid solution was poured into the reaction flask, and after vigorously stirring for 丨, the aqueous layer was collected by extraction, and the aqueous layer was extracted with diethyl ether (2×25 mL).

After removing the water and concentrating under reduced pressure, MgSO.sub. Ο

Example 3 Synthesis of Asymmetric Series Compounds 1·1 equivalent of l,4-dihydro-l,4-epoxytriphenylene and 1 equivalent of p-bromoiodophenylide, catalyzed by 5 mol% PdC12(PPh3)2

The agent 'phenylbenzene is a solvent, 5 equivalents of triethylamine, 5 equivalents of zinc powder is used as a source of reducing agent, the temperature is controlled at Π 0 X:, and the mixture is stirred for 1 day. After the reaction is finished, it is filtered to remove salts. The solid which was concentrated under reduced pressure was purified on a silica gel column eluting with ethyl acetate:hexane = 1:1. Yield 7 8 %~91 % 0 123313.DOC -20- 200914401

1 Γ --R-B +

2. Take 1.1 equivalents of l-pyrenyi boronic acid and 1 equivalent of bromo-(triphenylen-2-yl) aryl, using 5 mol % Pd(PPh3)4 as the catalyst 'toluene as solvent' 2 M potassium carbonate aqueous solution as alkali Source 〇 (both volume ratio 3: 1) 'Suzuki doing carbon-carbon bond addition

In the Coupling reaction, the reaction temperature is controlled at 1, and the reaction time is from j to 3 days. The yield was 71% to 88%.

Suzuki Coupling b(oh)2 3 _ The crude product synthesized was purified by sublimation twice, and the pressure at the time of sublimation was lower than 1 x 10-6 torr, and the sublimation temperature was regarded as the synthesized product. When synthesizing PT, PPT and PBT, the sublimation temperature is between 270 and 350 °C; 8? and? At 5 D, the sublimation temperature is between 250 and 310 C. The obtained sublimed product is subjected to various physical properties measurement, including ultraviolet-visible (UV-Vis) absorption spectrum, fluorescent (PL) emission spectrum 'difference scanning thermal analyzer (DSC), HOMO/LUMO (AC-II) and quantum fluorescence efficiency, the results are shown in Table 1 and Table 2 of 123313.DOC-21-200914401. Table 1 Photophysical properties of ruthenium, osmium, iridium, TST, PSP, PST (1) Compound type Xmax a Abs in toluene (nm) Xmax EM b in toluene (nm) Xmax EM (thin film) (nm) HOMO 0 (eV) LUMO (eV) Eg (eV) PT 346 404 460, 480 5.81 2.71 3.10 PPT 350 424 460 5.73 2.78 2.95 PBT 346 417 458 5.68 2.73 2.95 TST 370 420, 444 498 5.49 2.60 2.89 PSP 380 477 526 5.29 2.70 2.59 PST 372 482 514 5.34 2.70 2.64 a. UV-visible absorption concentration = lxl〇-5M b. Fluorescence concentration = 1χ10-5Μ c. HOMO measured by AC-II Ο Table 2 ΡΤ, ΡΡΤ, ΡΒΤ, TST, Photophysical properties of PSP, PST 4 Tether species Tg (°C) a Tc (°C)a Tm (°C)a Quantum yieldc (%) PT 110 NAb 255 95 PPT 115 NAb 223 97 PBT 135 170 273 99 TST NAb NAb 338 47 PSP 80 131 232 30 PST 105 144 214 42

B_ ΝΑ ^ can not measure the data c. Use 7-diethylamine, 4 methyl coumarin ic * crystalline temperature Tm: melting point temperature spectrum data ΡΤ Ϊ 2- (pyren-l-yl)tripheny!ene; 2-(1-蒎-based) three-fold stupid] 123313.DOC -22, 200914401

1H NMR (500 MHz, d-THF): d [ppm] 9.02 (s, 1 H), 8.95 (d, 1 H, J = 8.5 Hz), 8.87-8.85 (m, 1 H), 8.81-8.77 ( m, 4 H), 8.35 (d, 1 H, J = 8.5 Hz), 8.30 (d, 1 H, J = 9.5 Hz), 8.25 (d, 1 H, J = 8 Hz), 8.22- 8.15 (m , 4 H), 8.09 (d, 1 H, J = 9.5 Hz), 8.03 (t, 1 H, J = 8

Hz), 7.96 (d, 1 H, J = 8 Hz). 13C NMR (125 MHz, d-THF): d [ppm] 141.06, 140.67, 138.66, 132.57, 132.08, 13 1.29, 130.092, 130.67, 130.47, 130.10, 130.04, 129.90, 129.65, 129.54, 128.69, 128.31, 128.23, 128.19, 128.13, 127.68, 127.37, 126.90, 126.24, 126.03, 125.96, 125.81, 125.73, 125.56, 124.93, 124.60, 124.42, 124.36, 124.30, 124.27, 122.81. HRMS (EI+): calcd 428.1565, found 428.1564.

Elem Anal: calcd C 95.30 %, H 4.70 %, found C 94.38 %, H 4.60 %. PPT [ l-(pyren-l-yl)-4-(triphenylen-2-yl)benzene ; 1-(1-mask Base)-4-(2-linked triphenylene)benzene]

*H NMR (500 MHz, d-THF): ppm .9.16 (s, 1 H), 8.98-8.95 (m, 1 H), 8.91-8.87 (m, 1 H), 8.81-8.74 (m, 3 H ), 8.32-8.20 (m, 4 H), 8.16-8.01 (m, 7 H), 7.89 (d, 1 H, 7 = 8 Hz), 7.82 123313.DOC -23 - 200914401 (d, 1 H, J =8 Hz), 7.71-7.65 (m, 5 H). , 3C NMR (125 MHz, d-THF): ppm. 141.50, 141.43, 140.88, 138.37, 138.32, 137.77, 137.43, 132.56, 132.06, 131.93, 131.77 , 131.26, 131.11, 130.87, 130.75, 130.65, 130.08, 129.88, 129.66, 129.44, 129.33, 129.21, 129.12, 128.36, 128.22, 128.15, 127.52, 126.96, 126.89, 126.03, 125.91, 125.82, 125.72, 125.60, 125.02, 124.69 , 124,42, 124,29, 123.09, 122.46 HRMS (EI+): calcd 504.1878, found 504.1881. PBT [ 4-(pyren-l-yl)-4'-(triphenylen-2-yl)biphenyl ; 4-( 1-菜基)-4'-(2-linked triphenylene)biphenyl 1

'H NMR (500 MHz, d-THF): ppm . 9.11 (s, 1 H), 8.96-8.93 (m, 1 H), 8.87 (d, 1 H, 7 =8 Hz), 8.79-8.68 (m , 2 H), 8.31-8.21 (m, 4 H), 8.15-7.93 (m, 10 H), 7.88-7.58 (m, 9 H). Q HRMS (EI+): calcd 580.2191, found 580.2200.

Elem Anal: calcd C 95.14 %, H 4.86 %, found C 94.80 %, H 5.19 %.

PST

[2-(pyren-l-yl)-5-(triphenylen-2-yl)thiophene ; 2-(1-)-)-5-(2-linked triphenylene)thiophene 1

C38h22s 123313.DOC 24 200914401 'H NMR (500 MHz, d-THF): ppm .9.11 (s, 1 H), 8.90-8.88 (m, 1 H), 8.32 (d, 1 H, 7 =9 Hz) , 8.78-8.74 (m, 3 H), 8.68 (d, 1 H, J = 9 Hz), 8.30-8.14 (m, 6 H), 8.10-8.03 (m, 2 H), 7.88 (d, i H , J = 3 Hz), 7.74-7.64 (m, 4 H), 7.51 (d, 1 H, J -3 Hz), 7.39 (s, 1 H). 13C NMR (125 MHz, d-THF): ppm .146.08, 143.15, 134.12, 132.56, 132.20, 132.03, 131.31, 131.18, 130.81, 130.77, 130.56, 130.53, 130.22, 129.80, 129.77, 129.63, 129.22, 128.90, 128.70, 128.39, 128.17, 128.64, 127.09, 126.32, 126.03 , 125.99, 125.61, 125.33, 125.18, 124.71, 124.35, 124.28, 123.35, 123.10, 122.91, 120.70. HRMS (ΕΓ): calcd 510.1442, found 510.1445.

Elem Anal: calcd C 89.03 %, H 4.72 %, S 6.25 %, found C 89.25 %, H 4.56%, S6.11 %. Examples 4 to 6 4 Examples 4 to 64 are the use of the novel compounds of the invention as luminescent materials An example of the fabrication of an organic electroluminescent device. The organic electroluminescent device of the present invention comprises an anode, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode. A hole injection layer can be placed between the anode and the hole transfer layer, and can also be illuminated. A hole blocking layer is interposed between the layer and the electron transport layer. The anode is an IT〇' hole injection layer material such as CuPc, PEDOT: PSS and 4,4,4 -叁(3·曱(phenyl)amino)triphenyl (4,4,,4| |七is(3_

y pllenyKpheny 1) ami no )tri phenyl amine, m-MTDATA), etc., the hole transport layer material can be NPB and TPD; the hole resist layer material can be, methyl diphenyl-1,10-phenoline ( 2,9-dimethyl-4,7-123313.DOC -25- 200914401 diphenyl-l,10-phenanthroline,BCP),ί吕双(2-methyl-8-0 quinolate)4-phenylphenylhydrazine Salt (aluminumUII^bisP-methyl-S-quinolinatoM-phenylphenolate, BAlq) and TPBI; electron transport layer materials such as Alq and TPBI; cathode materials can be divided into two types, the first is magnesium silver, the second is Lithium fluoride and aluminum. • Example 4: pt-1 : ITO/NPB (50 nm) / PT (30 nm) / TPBI (40 nm) / Mg: Ag (55 nm) / Ag (100 nm) Example 5: pt-2 : ITO / NPB (50 nm) / PT (30 nm) / TPBI (40 nm) / LiF (l 〇 nm) / Al (100 nm) Example 6 : pt-3 : ITO / NPB (50 nm) / PT (30 nm) /TPBI(10 nm)/Alq(30 nm)/Mg: Ag(55 nm)/Ag(100 nm) Example 7 ·· pt-4 : ITO/NPB (50 nm) / PT (30 nm) / TPBI ( 10 nm) / Alq (30 nm) / LiF (l nm) / Al (100 nm) Example 8 : pt-5 : ITO / NPB (50 nm) / PT (30 nm) / BCP (10 nm) / Alq ( 30 nm) / Mg: Ag (55 nm) / Ag (100 nm) Example 9 : pt-6 : ITO / NPB (50 nm) / PT (30 nm) / BAlq (10 nm) / Alq (30 nm) / Mg: Ag (55 nm) / Ag (100 nm) Example 10: pt-7 : ITO/CuPc (10 nm) / NPB (50 nm) / PT (30 nm) / TPBI (40 ; nm) / LiF (1 Nm) / Al ( 100 nm) • Example 11 : pt-8 : ITO / TPD (50 nm) / PT (30 nm) / TPBI (40 nm) / Mg: Ag (55 nm) / Ag (100 nm) Example 12 : pt-9 : ITO/TPD (50 nm) / PT (30 nm) / TPBI (40 nm) / LiF (l nm) / Al (100 nm) Example 13 : ppt-1 : ITO / NPB (50 nm ) / PPT (30 nm) / TPBI (40 123313.DOC -26 - 200914401 nm) / Mg: Ag (55 nm) / Ag (100 nm) Example 14 : ppt-2 : ITO / NPB (50 nm) / PPT (30 nm) / TPBI (40 nm) / LiF (l nm) / Al (100 nm) Example 15 : ppt-3 : ITO / NPB ( 50 nm)/PPT (30 nm)/TPBI (10 nm)/Alq (30 nm)/Mg: Ag (55 nm)/Ag (100 nm) Example 16: ppt-4: ITO/NPB (50 nm)/ PPT (30 nm) / BCP (10 nm) / Alq (30 nm) / Mg: Ag (55 nm) / Ag (100 nm) Example 1 7 : ppt-5 : ITO / CuPc (10 nm) / NPB (50 Nm)/PPT(30 nm)/TPBI(40 nm)/LiF(l nm)/Al(100 nm) Example 18: ppt-6: ITO/TPD (50 nm)/PPT (30 nm)/TPBI (40 Nm)/Mg: Ag(55 nm)/Ag(100 nm) Example 19: ppt-7: ITO/TPD (50 nm) / PPT (30 nm) / TPBI (40 nm) / LiF (l nm) / Al (100 nm) Example 20: ppt-8: ITO/TPD (50 nm) / PPT (30 nm) / TPBI (10 nm) / Alq (30 nm) / Mg: Ag (55 nm) / Ag (100 nm) Example 21: ppt-9: ITO/TPD (50 nm) / PPT (30 nm) / TPBI (10 nm) / Alq (30 nm) / LiF (l nm) / Al (100 nm) Example 22: ppt-10 : ITO/CuPc (10 nm) / TPD (50 nm) / PPT (30 nm) / TPBI (40 nm) / LiF (l nm) / Al (100 nm) Example 23: pbt-1 : ITO / NPB (50 Nm)/PBT(30 nm)/TPBI(40 nm)/Mg: Ag(55 nm)/Ag(100 nm) Example 24: pbt-2: ITO/NPB (50 nm)/PBT (30 nm)/TPBI (40 nm) / LiF (l nm) / Al (100 nm) Example 25: pbt-3 : ITO / NPB (50 nm) / PBT (30 nm) / TPBI (10 nm) / Aki (30 123313.DOC - 27- 200914401 nm)/Mg: Ag(55 nm)/Ag(100 nm) Example 26: pbt-4 : IT O/NPB (50 nm) / PBT (30 nm) / TPBI (10 nm) / Alq (30 nm) / LiF (l nm) / Al (100 nm) Example 27: pbt-5 : ITO / NPB (50 nm ) / PBT (30 nm) / BCP (10 nm) / Alq (30 nm) / Mg: Ag (55 nm) / Ag (100 nm) Example 28: pbt-6: ITO / CuPc (10 nm) / NPB ( 50 nm)/PBT (30 nm)/TPBI (40 nm)/Mg: Ag (55 nm)/Ag (100 nm) Example 29 ·· pbt-7 : ITO/CuPc (10 nm)/NPB (50 nm) /PBT(30 om)/TPBI(40 nm)/LiF(l nm)/Al(100 nm) Example 30: pbt-8 : ITO/TPD (50 nm) / PBT (30 nm) / TPBI (40 nm) /Mg: Ag (55 nm) / Ag (100 nm) Example 31: pbt-9 : ITO / TPD (50 nm) / PBT (30 nm) / TPBI (40 nm) / LiF (l nm) / Al (100 Nm) Example 32: pbt-10 : ITO/TPD (50 nm) / PBT (30 nm) / TPBI (10 nm) / Alq (30 nm) / Mg: Ag (55 nm) / Ag (100 nm) Example 33 : pbt-11 : ITO/TPD (50 nm) / PBT (30 nm) / TPBI (10 nm) / Alq (30 nm) / LiF (l nm) / Al (100 nm) Example 34 : pbt-12 : TO /CuPc(10 nm)/TPD(50 nm)/PBT(30 nm)/TPBI(40 nm)/Mg: Ag(55 nm)/Ag(100 nm) Example 3 5 : pbt-13 : ITO/CuPc( 10 nm) / TPD (50 nm) / PBT (30 nm) / TPB 1 (40 nm) / LiF (l nm) / Al (100 nm) Example 3 6 : tst-1 : ITO / NPB (50 nm) / TST (30 nm) / TPBI (40 nm) / Mg: Ag (55 nm) / Ag (100 nm) Example 37 : tst-2 : IT O/NPB (50 nm) / TST (30 nm) / TPBI (40 nm) / LiF (l I233I3.DOC -28 - 200914401 nm) / Al (100 nm) Example 38: tst-3 : ITO / NPB (50 Nm)/TST(30 nm)/TPBI(10 nm)/Alq(30 nm)/Mg: Ag(55 nm)/Ag(100 nm) Example 39: tst-4: ITO/NPB (50 nm)/TST (30 nm) / BCP (10 nm) / Alq (30 nm) / Mg: Ag (55 nm) / Ag (100 nm) Example 40: tst-5 : ITO / CuPc (10 nm) / NPB (50 nm) /TST (30 nm) / TPBI (40 nm) / Mg: Ag (55 nm) / Ag (100 nm) Example 41 : tst-6 : ITO / CuPc (10 nm) / NPB (50 nm) / TST (30 Nm)/TPBI(40 nm)/LiF(l nm)/Al(l00 nm) Example 42: tst-7: ITO/TPD (50 nm)/TST (30 nm)/TPBI (40 nm)/Mg: Ag (55 nm) / Ag (100 nm) Example 43 : tst-8 : ITO / TPD (50 nm) / TST (30 nm) / TPBI (40 nm) / LiF (l nm) / Al (100 nm) Example 44 : tst-9 : ITO/TPD (50 nm) / TST (30 nm) / TPBI (10 nm) / Alq (30 nm) / Mg: Ag (55 nm) / Ag (100 nm) Example 45: tst-10 : ITO/CuPc (10 nm) / TPD (50 nm) / TST (30 _) / TPBI (40 nm) / Mg: Ag (55 nm) / Ag (100 nm) Example 46 : tst-11 : ITO / CuPc (10 nm) / TPD (50 nm) / TST (30 nm) / TPBI (40 nm) / LiF (l nm) / Al (100 nm) Example 47: psp-1 : ITO / NPB (50 nm) / PSP (30 nm) / TPBI (40 nm) / Mg: Ag (55 nm) / Ag (100 nm) Example 48: psp- 2 : ITO/NPB (50 nm) / PSP (30 nm) / TPBI (40 nm) / LiF (l nm) / Al (100 nm) Example 49 : psp_3 : ITO / CuPc (10 nm) / NPB (50 nm /PSP (30 nm) / TPBI (40 I23313.DOC -29- 200914401 nm) / Mg: Ag (55 nm) / Ag (100 nm) Example 50 : psp-4 : ITO / CuPc (10 nm) / NPB (50 nm) / PSP (30 nm) / TPBI (40 nm) / LiF ( 1 nm) / Al ( 100 nm) Example 5 1 : psp-5 : ITO / TPD (50 nm) / PSP (30 nm) / TPBI (40 nm) / Mg: Ag (55 nm) / Ag (100 nm) Example 52 : psp-6 : ITO / TPD (50 nm) / PSP (30 nm) / TPBI (40 nm) / LiF (l nm ) / Al (100 nm) Example 53 : psp-7 : ITO / CuPc (10 nm) / TPD (50 nm) / PSP (30 nm) / TPBI (40 nm) / Mg: Ag (55 nm) / Ag ( 100 nm) Example 54: psp-8: ITO/CuPc (10 nm) / TPD (50 nm) / PSP (30 nm) / TPBI (40 nm) / LiF (l nm) / Al (100 nm) Example 5 5 : pst-1 : ITO/NPB (50 nm) / PST (30 nm) / TPBI (40 nm) / Mg: Ag (55 nm) / Ag (100 nm) Example 56 : pst-2 : ITO / NPB (50 Nm)/PST (30 nm) / TPBI (40 nm) / LiF (l am) / Al (100 nm) Example 57 : pst-3 : ITO / CuPc (10 nm) / NPB (50 nm) / PST (30 Nm)/TPBI(40 nm)/Mg: Ag(55 nm)/Ag(100 nm) Example 58: pst-4: ITO/CuPc(10 nm)/NPB(50 nm)/PST(30 nm)/TPBI (40 nm) / LiF (l nm) / Al (100 nm) Example 59 : pst-5 : ITO / m- MTDATA (10 nm) / NPB (50 nm) / PST (30 nm) / TPBI (40 nm) / Mg: Ag (55 nm) / Ag (100 nm) Example 60: pst-6 · · ITO / m-MTDATA (10nm ) / NPB (50 nm) / PST (30 nm) / TPBI (40 nm) / LiF (l nm) / Al (100 nm) Example 61 : pst-7 : ITO / TPD (50 nm) / PST (30 nm) /TPBI(40 1233 13.DOC -30- 200914401 nm)/Mg: Ag(55 nm)/Ag(100 nm) Example 62: pst-8: ITO/TPD (50 nm)/PST (30 nm)/TPBI (40 nm) / UF (l nm) / Al (100 nm) Example 63 : pst-9 : ITO / CuPc (10 nm) / TPD (50 nm) / PST (30 nm) / TPBI (40 nm) / Mg :Ag(55 nm)/Ag(100 nm) Example 64: pst-10 : ITO/CuPc(10 nm)/TPD(50 nm)/PST(30 nm)/TPBI(40 nm)/LiF(l nm) /Al(100 nm) Table 3 PT, PPT, PBT, TST, PSP and PST as organic light-emitting element properties of luminescent layer materials. Best external quantum efficiency % (volts) maximum brightness (cd/m2) Volt) Best Current Efficiency (cd/A) (Volt) CIE Coordinate (x, y) (8V) ----- Light Color Example 4 2.47 (7.0) 21801 (18.5) 4.03 (7.0) (0.15, 0.21) Blue ΐ~' Example 5 2.60(6.5) 24225(20.5) 4.13(6.5) (0.15, 0.19) Basket ΐ~~ Example 6 1.83(9.0) 14593(1 9.5) 3.11(9.0) (0.16, 0.21) Blue^— " Example 7 2 .35(6.0) 23734(1 9.5) 3.93(6.0) (0.16, 0.22) — ... Blu-ray example 8 1.54(8.5) 14460(1 8.5) 3.01(8.5) (0.17, 0.27) ——— Blu-ray example 9 1.64 ( 10.0) 14779(1 6.5) 3.39(10.0) (0.17, 0.29) ----- Basket example 1 0 2.43(7.5) 30148(19.0) 4.98(7.5) (0.17, 0.29) —--- — Example of Blu-ray 11 2.13(6.5) 1 8325(1 5.0) 3.21(6.5) (0.15, 0.20) Example of blue light 12 2.48(5.5) 19498(1 8.0) 3.66(5.5) (0.15, 0.19) Blue Τ ''' Example 1 3 3.79 (8.5) 29757(20.0) 6.26(8.5) (0.14, 0.20) Basket ΐ~~ Example 14 4.38(4.0) 3875 1(19.5) 6.33(4.0) (0.15, 0.17) Blu-ray example 1 5 3.49(7.5) 27455( 21.5) 6.26(7.5) (0.15, 0.22) Blue Γ'' Example 1 6 2.79(9.0) 22359(1 8.5) 3.89(9.0) (0.14, 0.16) blue ί~ Example 17 3.89(8.5) 64194(20.0) 8.26 (8.5) (0.16, 0.27) ---- Blu-ray • — _ 1233 13.DOC -31 - 200914401 Example 1 8 3.82(7.0) 5 1 833( 1 7.5) 7.31(7.0) (0.15, 0.24) Blu-ray example 1 9 4.59(3.5) 57848( 19.0) 8.44(3.5) (0.15, 0.24) Example of blue light 20 3.93(5.0) 29301(20.0) 7.31(5.0) (0.16, 0.23) Example of blue light 2 1 4.57(4.0) 39281(20.0) 7.25 (4.0) (0.14, 0.19) Blu-ray example 22 3.92(8.0) 39966( 1 5.5) 6.42(7.5) (0.15, 0.20) Example of blue light 23 4.25(5.0) 29848(17.0) 4.36(5.0) (0.14, 0.11) Blu-ray Example 24 4.95(4.5) 34002(2 1.5) 4.80(4.5) (0.14, 0.11) Example of blue light 25 4.08(7.0) 32553( 1 7.5) 5.76(7.0) (0.15, 0.17) Example of blue light 26 5.05(4.5) 38549( 16.5) 6.32(4.5) (0.15, 0.14) Blu-ray example 27 3.05(9.0) 25879(1 8.5) 4.68(9.0) (0.15, 0.18) Blu-ray example 2 8 4.60(7.5) 40979(1 8.5) 6.19(8.0) ( 0.15, 0.16) Blue light example 29 5.23(7.0) 41 698(18.5) 5.77(7.0) (0.14, 0.12) Blue light example 30 2.21(10.5) 26171(17.5) 3.34(11.0) (0.15, 0.18) Blue light example 3 1 2.78 (6.5) 25436 (1 6.5) 3.51 (6.5) (0.14, 0.14) Example of blue light 32 2.53 (8.0) 23862 (1 8.0) 3.73 (8.0) (0.15, 0.18) Example of blue light 33 2.62 (5.5) 271 55 (16.0) 3.91(6.0) (0.15, 0.18) Blue light example 34 3.07(8.5) 25191(17.0) 4.28(8.5) (0.14, 0.16) Blue light example 35 3.28(7.5) 25079(1 6.5) 4.18(7.5) (0.14, 0.15) Blu-ray example 36 2.22(5.5) 46486(1 7.0) 6.37(5.5) (0.20, 0.48) Example of blue-green light 37 2.37(5.0) 4 9664(20.5) 7.34(5.0) (0.24, 0.51) Example of blue-green light 3 8 2.00(5.5) 29190(1 9.0) 5.70(5.5) (0.20, 0.48) Example of blue-green light 39 1.89(5.5) 271 1 7( 20.5) 5.12(5.5) (0.19, 0.46) Example of blue-green light 40 1.97(9.0) 30843(2 1.0) 6.51(7.5) (0.25, 0.54) Example of blue-green light 4 1 2.60(4.5) 40405(20.0) 8.45( 4.5) (0.24, 0.54) Example of blue-green light 42 2.38(5.5) 42865(1 8.0) 6.54(5.5) (0.19, 0.46) Blu-ray I233I3.DOC -32- 200914401 Example 43 2.93(5.0) 4573 1(1 8.5) 8.76(5.0) (0.21, 0.50) Example of blue light 44 1.88(5.5) 26472(19.5) 5.05(5.5) (0.19, 0.45) Example of blue light 45 1.73(7.5) 27780(17.5) 4.57(7.5) (0.18, 0.45) Blue light Example 46 2.24(5.5) 30139(1 6.0) 6.21(5.5) (0.19, 0.46) Example of blue light 47 1.60(7.0) 423 1 8(1 7.0) 5.50(7.0) (0.24, 0.61) Green light example 48 1.79 (6.0 48 124(16.5) 6.05(6.0) (0.24, 0.60) Green Light Example 49 1.63(7.5) 44374(1 7.5) 5.57(7.5) (0.25, 0.60) Green Light Example 5 0 1.72(5.5) 42836(16.5) 5.80(5.5) (0.24, 0.60) Green light example 5 1 1.41(9.0) 3935 1(17.5) 4.60(9.0) (0.24, 0.58) Green light. Example 52 1.50(8.0) 4171 6(20.0) 5.03(8.0) (0.25, 0.59) Green light example 5 3 1.97(8.0) 44098(17.0) 6.97(8.0) (0.26, 0.61) Green light example 5 4 2.29(6.0) 46606(1 5.0) 7.96 (5.5) (0.25, 0.61) Green light example 55 1.76 (7.0) 54950 (17.0) 6.35 (7.0) (0.29, 0.60) Green light example 5 6 2.13 (5.0) 68834 (16.5) 7.60 (5.0) (0.29, 0.60 ) Green light example 5 7 2.14(7.5) 61373(1 8.5) 7.81(7.5) (0.28, 0.61) Green light example 5 8 2.36(5.0) 7033 1(1 8.0) 8.49(5.0) (0.27, 0.61) Green light Example 59 2.91 (10.0) 65987 (20.0) 10.66 (10.0) (0.30, 0.61) Green light example 60 3.10 (8.0) 72327 (19.5) 11.35 (8.0) (0.30, 0.61) Green light example 61 1.81 (7.5) 52980 ( 1 6.0) 6.19(7.5) (0.27, 0.59) Green light example 62 2.20(4.5) 60858(16.0) 7.46(4.5) (0.26, 0.59) Green light example 63 1.94(7.0) 491 70(1 6.0) 7.15(7.0 (0.29, 0.61) Green light example 64 2.38 (5.0) 45267 (1 5.0) 8.26 (5.0) (0.26, 0.60) Green light can be seen from Table 3 using the asymmetric organic compound of the present invention as blue light and green light The luminescent materials of the organic electroluminescent elements all have good performance of I23313.DOC 03 - 200914401. After the components are made, both ΡΡΤ and ΡΒΤ can achieve very good performance. In terms of enthalpy, the maximum brightness can reach 64 〖94 Cd/m2, and the optimal external quantum efficiency is also 459%, and the optimum current efficiency and optimal energy efficiency are also 8.44 cd/A and 7.59 lm/ respectively. W; in terms of enthalpy, the maximum το degree can reach 41698 cd/m2, while the optimal external quantum efficiency exceeds the theoretical limit of fluorescence by up to 5.23%, and the optimum current efficiency and optimum energy efficiency are also 6 32 respectively. Cd/A* 4 89 lm/w. Since both Ding and A are excellent blue light materials, they can be further used in research on white light. In terms of PST, the glass transition temperature (Tg) of pst can reach 105 C and the pst-6 of example 60 can reach 72327 in terms of maximum brightness and 3iq % in optimal external quantum efficiency. The best current efficiency = good energy. In terms of efficiency, there are also η·35 ed/A and 4·6(1)(10), which is a good bond loyalty u, 'eight precursor materials, and can further use PST in the study of white 蛍 兀 。. The scope of the following patent application is intended to be clear to those skilled in the art, and the improvement of the various modifications that can be achieved by the invention is also within the reasonable scope of protection of the present invention.

I23313.DOC 34·

Claims (1)

200914401 X. Patent application scope: 1. A compound of the formula (I), Ar1-R-Ar2 (I) wherein Ar1 and Ar2 are a triphenylene or anthracenyl group, and Ri is a bond, an aromatic group, or Aromatic heterocyclic group. 2. The compound of formula (I) according to claim 1, wherein the aryl group is selected from the group consisting of phenyl O (Pheny丨), naphthyl, biphenyl (Dipheny, anthryl, benzophenanyl) a group consisting of (Pyreny®), phenanthryl and dibenzopentacyclic (Fluorene), and other forms of polycyclic ring-substituted biphenyl groups. 3. A compound of formula (I) according to claim 1 Wherein the aromatic heterocyclic group is selected from the group consisting of Pyrane, Pyrroline, Furan, Benzofuran, Thiophene, Benzothiophene, 0 ratio. (Pyridine), 嗤♦ (Quinoline), isoquinoline (isoquinoline), pyrazine, pyryidine, pyrrole, alpha ratio, Pyrazole, σ meter Imidazole, Indole, α-plug, Thiazole, Isothiazole, 0 evil, Oxazole, Isoxazole, stupid 11 Benzothiazole, Benzoxazole, 1,2,4_3, δ>^(1,2,4-ΤΓί&ζο1ε), 1 2, 3-5°.^0^(1,2,3-ΤΗ&ζο1ε),: a group of Phenanthroline, and other forms of heteronuclear aromatic rings. 1233I3.DOC 200914401 4.Request The compound of the formula (I) of the formula 1 wherein Ar, Ar2 and R1 are independently optionally substituted by one or more substituents selected from the group consisting of nitrogen, a aryl group, an aryl group, a halogen-substituted aryl group, and a halogen a substituted aromatic alkyl group, an i-alkyl substituted aromatic group, a haloalkyl-substituted aromatic group, an aryl-substituted C1-C20 alkyl group, an electron-donating group, an electron-withdrawing group, and a heterocyclic substituent group 5. A compound of the formula (I) according to claim 4, wherein the electron-donating group comprises (: 丨_(: 2〇 alkyl, C1-C20 cycloalkyl, C1-C20 alkoxy, C1_C2〇 substituted 2 Or an aromatic amine group having a substituent. 6. The compound of the formula (1) according to claim 4, wherein the electron withdrawing group comprises dentate, nitrite group, wall group, several groups, cyano group, dentate substitution (10) cardinalization 70. 7. As the compound of formula (1) of the formula i, wherein 1 is ^2, ^ is a heterocyclic group. "方杳 8. As in the case of claim 1 (1) Thereof, wherein Rl is square when ⑷ - key, the compound of formula of formula ⑴ (the PT); or (b) When R1 is a phenyl group, Ar1 and Ar2 are not (pPT); or the same, the compound of the formula (I) is of the formula I23313.DOC 200914401 (c) when R1 is a phenyl group and Ar1 is different from Ar2, the compound of the formula (1) is a formula (PBT); (PBT) Ο is a thiophene group, αγι=αγ2=linked to a phenyl group. The compound of the formula (I) is a formula (TST); (TST) (4) When R1 is a thienyl group and Ari=Ar2=fluorenyl, the compound of the formula (I) is of the formula 123313.DOC 200914401 (psp); (PSP) (f) When R is a p-enyl group and Ar1 is different from Ar2, the compound of the formula (I) is a formula (PST) A method for producing a compound of the formula (1) according to claim 1, which comprises, (a) reacting a compound of the formula (ΙΠαΛΙ^-Χ1 with an Ar2-Y compound of the formula (III) when R1 is a bond; (1) a compound; or W-R1-X1 + Ar2-Y Now Ar1-R1-Ar2 (II) (HI) (I) (b) When R is an aromatic group or an aromatic heterocyclic group, and Ari is different from Ar2, Reacting a compound of the formula (π) ΑΓι-ρΛχΐ with a compound of the formula (III) Ar2_Y to form a compound of the formula (1); or (c) when R1 is an aryl group or an aromatic heterocyclic group, and Arl = Ar2 = a triphenylene group, The compound of formula (IV) is reacted with the compound of formula (v) x2_r1_x3 to form 123313.DOC 200914401 (d) when R is an aromatic or aromatic heterocyclic group, Arl = Ar2 = 蒎, the compound of formula (III) Ar2-Y is reacted with a compound of formula (v) x2_r1_x3 to form a compound of formula (I); + X2-R'-X3 Ar丨—R丨—Ar2 (ΠΙ) (V) (I) wherein X1, X2, X3 are a gas atom (Cl), a bromine atom (Br) or an iodine atom (1), and Y is hydrogen peroxide. Boron (B(OH)2). 10. The method of claim 9, wherein the Ari-Ri-X1 compound of the formula (II) is formed by reacting a compound of the formula (IV) with a compound of the formula (V) xLrLx3. 11. The method of claim 9, wherein the reaction in steps (a), (b) and (d) is a Suzuki Coupling reaction. 123313.DOC 200914401 wherein the reaction of step (c) is Coupling anti-12. The method of claim 9 should be 0. 13. As in the method of claim 10, Γ γ w M ° 茨久 should be coupling for a long time. An organic electroluminescent device, characterized in that the luminescent layer is a luminescent material having the compound of the formula (I) according to claim 1, 15. The luminescent element of claim 14, the electron transporting layer, and a cathode. 16. The light-emitting element of claim 15 wherein the hole injection layer between the transport layers is 17. The light-emitting element of claim 15 wherein the hole blocking between the sub-transport layers further comprises an anode, a hole transport layer, It further includes the anode and the hole, which further comprises the luminescent layer and the electrical layer. When the compound of the formula (1) is considered to be "1" 8. The light-emitting element of claim 14, when the f-bond or the aromatic group is emitted, the blue light is emitted. 19. The light-emitting element of the claim I4 is judged by the slice * Dan. (I) R1 of the compound is an aromatic heterocyclic group, and when Ar1 and Ar2 are different - 1′′, when it is a bi-extension, it emits green light. 20. The luminescence τ of claim 14, wherein when the r| of the compound of the formula (1) is an aromatic heterocyclic group 'Ar*Ar2 is simultaneously a triple extension*, and NpB is a hole transport layer, blue green is emitted Light. The luminescent member according to claim 14, wherein when r| of the compound of the formula (1) is an aromatic heterocyclic group, Ar and Ar2 are simultaneously a ternary benzene, and when TpD is a hole transport layer, blue light is emitted. 123313.DOC 200914401 VII. Designation of Representative Representatives (1) The representative representative of the case is: (none) (2) A brief description of the symbol of the representative figure: 〇8. If there is a chemical formula in this case, please reveal the best indication of invention. Characteristic chemical formula: Ar1- R-Ar2 (I) 1233I3.DOC