TWI268951B - Organic electroluminescent device - Google Patents

Abstract

An organic electroluminescent device at least includes a first electrode, an organic electroluminescent layer, and a second electrode, sequentially installed on a substrate; in which the material used by the organic electroluminescent layer includes a compound with the following formula (I).

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an organic electroluminescent material and an organic electro-acoustic device thereof, and more particularly to an organic electro-acoustic 5 luminescent material containing a Styrylbenzene. Organic electroluminescent elements. [Prior Art] With the advancement of electronic technology, the lightweight and efficient display has been vigorously developed with the 10 15 and gradually replaced the traditional image tube display (CRT), such as liquid crystal display (LCD). There are many shortcomings, for example, the angle of view is not wide enough, and the response time is not fast enough, so it cannot be used under high speed. And it needs to use a polarizer " light board, thus: adding power, reset and cost. In addition, the LCD panel still cannot easily make large panels. In view of this, the organic electroluminescent device (in which the inescent device) has its advantages of self-luminescence, no viewing angle limitation, easy power saving, easy process, low cost, high response speed, and full coloring, so that the organic electroluminescent light is made. The components have great potential for application, and can be used for: flat panel displays and planar light source illumination, including special light sources and general illumination elements including _-... soil 4 π —— electric maple, one; electroluminescence a layer and a second electrode. #帝激笋弁...士+ or current in organic f, / piece r(4) and electron system respectively by the first electrode and the second electrode/in, due to the potential difference caused by the applied electric field, the carrier is excited by the organic electricity 20 1268951 The layers move and meet to recombine, and the exciton generated by the recombination of electrons and holes can excite the luminescent molecules in the organic electroluminescent layer. Then the excited luminescent molecules are released in the form of light. Energy 'where the luminescent molecules include small molecules and high molecular organic electroluminescent light 5 materials. As mentioned above, research on organic materials for organic electroluminescent layers has been developed for a long time. For example, W. Helfrish, Dresmer, Williams and others succeeded in making Anthrancene crystals emit blue light.

Chem. Phys. 1966, 44, 2902), in addition, Vincett, Barlow et al., 10 deposited a polyaromatic ring compound by vapor deposition to produce a light-emitting element (Thin Solid Film, 1982, 94, 2902), however, The light-emitting element has a low luminous intensity and a low luminous efficiency. In 1987, C. W. Tang and SA VanSlyke published a two-layer structure for the design of organic electroluminescent layers, which consisted of an organic thin film layer and a thin 15 layer containing holes or electron transport properties. The characteristics of the organic electroluminescent layer have different luminescent chromaticities depending on the energy level difference between the ground state and the excited state of the material. The maximum brightness of the green light emitted reaches 1000 cd/m2, and the luminous efficiency reaches 丨丨(5)/...卯丨%

Lett, 1987, 51, 913); followed by a three-layer structure as shown in Japanese j〇urnal 〇f Applied Physics, 1988, 27, 2, L269-L271 and Journal of Applied 20 Physics, 1989, 9, 3610 The electromechanical excitation layer 'is reduced the driving voltage of the organic electroluminescence element and the brightness thereof. The three-layer structure is an organic electroluminescence layer, a hole transmission layer and an electron transport layer. Among them, the luminescent material is the most important material in the organic electroluminescent device, and the material for selecting the organic electroluminescent layer needs to meet at least four requirements. 1268951 The first is to have high fluorescence quantum efficiency, and the luminescence peak is in the visible region, the wavelength range is narrow; the second is good semiconductor characteristics, that is, high conductivity, conduction of electrons or holes, or both The third is that it has a good film forming property, and the film does not have pinholes; and the fourth is that it has good thermal stability, does not crack under high temperature evaporation, and the film is not easily crystallized. . Since most organic dyes have a problem of concentration quenching in the solid state, causing the peak of the fluorescence to broaden or red shift, it is generally doped in a low concentration manner in a host having electron or hole transport properties (USP) 1〇4,769,292). The absorption spectrum of the dye needs to have a good overlap with the emission spectrum of the host, so that energy can be efficiently transferred from the host molecule to the guest molecule. Derivatives of distyrylbenzene generally have good quantum efficiency, and can easily adjust their luminescent color by a functional group. At present, derivatives of distyrylbenzene have been used in organic electro-acoustic 15 illuminating elements, for example, Japanese Idemitsu Corporation issued a number of related compounds, USP 5,121,029, USP 5,126,214, USP 5,130,603, USP 5,516,577, USP 5,536,949 , USP 6,093,864 and W002/20459. Sony also publishes patents EP0960927, EP1072668, EP1073128, USP 6,228,514 for related compounds. Itb, also reported in the literature 20, using styrylbenzene compounds and their derivatives as organic electroluminescent materials, such as Synthetic Metal, 2001, 121, 166, Synthetic Metal, 2001, 121, 1665, Appl· Phys. Lett· 1995, 67, 26, Engineering B, 2001, 85, 126 and Org· Lett·, 2003, 5, 1 131 and the like. Derivatives of styrylbenzene have been extensively studied for use in organic 1268951 electroluminescent materials and their organic electroluminescent devices, but there are always some shortcomings such as insufficient brightness, low luminous efficiency, high driving voltage, low color purity, etc. problem. For example, as shown in USP 5,130,603, it is made using 5 N,N9 - diphenyl-oxime, Ν9-bis-(3-methylphenyl)-[ 1515-biphenyl]-4,4'-diamine (TPD). It is a hole transport layer, and 2,5-bis(2,2-di-p-tolyvinyl)xylene (DTVX) is used as the organic electroluminescence layer. As a result, the luminance is 300 cd/m2 at 5V. The emission wavelength is 486 nm, and at 7 V, the luminance is up to 1000 cd/m2. 10 In addition, in USP 5,536,949, TPD is used as a hole transport layer, 4,4'-Bis(2,2_diphenylvinyl)biphenyl (DPVBi) is used as an organic electroluminescent layer, and the organic electroluminescent layer is It is doped with 4,4'-Bis[2-{ 4-(Ν,Ν-diphenyl amino)pheny } vinyl]biphenyl (DPAVBi), and then 8-hydroxyquinoline is used as the electron transport layer, and the junction 15 is at 8V. The luminance of the light is 400 cd/m2, and the emission wavelength is 494 nm. Furthermore, the results shown in USP 6,093,864 are similar to the above, and the distyrylbenzene series derivatives are formed in an organic electroluminescent device by vacuum evaporation, and the thermal stability of the molecules is poor, which is carried out in actual production. In the test, even the case of molecular lysis occurred. Therefore, it is difficult and complicated to apply to actual mass production. SUMMARY OF THE INVENTION The object of the present invention is to provide an organic electroluminescent material and an organic electroluminescent device thereof, which can stabilize a double bond which is easily cleaved in a material, and provides 1268951

Wherein R6&R7 are each independently substituted or unsubstituted alkyl having 1 to 10 carbon atoms, substituted or unsubstituted aromatic hydrocarbon group of 6 to 30 carbon atoms, aromatic complex cyclic group, or aromatic alkyl. The organic electroluminescent material of the present invention is not limited, and preferably comprises any group selected from the group consisting of the following compounds:

1268951

-r compound 8

Compound 9

Η

12 1268951

The compound of the formula (I) used in the organic electroluminescent device of the present invention can be used as a dopant for any of the organic material layers of the organic electroluminescent device, preferably as a hole. The dopant of the transport layer; the doping concentration used is not limited, and is preferably from 1 wt% to 30 wt%. The invention further comprises an organic electroluminescent device comprising at least a first electrode, an organic electroluminescent layer and a second electrode arranged in sequence on a group 13 1268951 group hydrocarbon group, having a radical of 6 to 30 carbon atoms An aromatic or unsubstituted aromatic heterocyclic unsubstituted aralkyl group having a substituted or unsubstituted or substituted group of 6 to 30 carbon atoms. ~~~, Ding", κΑ (丄) compound A r bond object is not limited, and the bond between Α and Β is not limited; organic light 兀 巾 (4) electric excitation light (four) , preferably ^ is selected from the following group of substituents riding group red group ·· ^

5

Wherein Re and R are each independently, substituted or unsubstituted alkyl having 1 to 1 carbon atom, substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, aromatic complex cyclic group Or an aralkyl group; the organic electroluminescent material used in the organic electroluminescent device of the present invention is not limited, and preferably comprises any group selected from the group consisting of: 15 1268951

Compound 11

16 1268951

In the organic electroluminescent device of the present invention, the hole transporting material is not limited, and preferably includes an aromatic amine compound having an aromatic hydrocarbon group-substituted aromatic polycyclic group substituent, and aroma. 17 Ϊ 268951 Group diamine compound or aromatic triamine compound; the hole transporting material used is not limited, and it is preferred that the glass transition temperature is greater than 1 〇 (rc) used in the organic electroluminescent device of the present invention. The substrate is not limited and may be a plastic substrate or a flexible substrate such as a polycarbonate (PC) substrate or a polyester (pET) substrate, preferably a transparent substrate. 10 15 20 The electrode used is not limited to a preferred transparent electrode; in the device of the present invention, the organic electroluminescent layer sandwiched between the first electrode and the second electrode is not limited, preferably one or more layers. The laminated structure; the laminated structure used therein is not limited, and preferably includes a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer or an electron injection layer, and a combination thereof; the organic electroluminescent layer The combination is not limited, preferably anode/light emitting layer/cathode, anode/light emitting layer/electron transport layer/cathode, anode/hole transport layer/light emitting layer/cathode, anode/hole transport layer/light emitting layer/electron Transport layer/cathode, anode/hole injection layer/hole transport layer/light-emitting layer/cathode, anode/hole injection layer/hole transport layer/light-emitting layer/electron transport layer/cathode, or anode/hole injection Layer/hole transport layer/light-emitting layer/electron transport layer/electron transport injection/cathode, etc. ^ The formation mode of the laminated structure in the organic electroluminescent device of the present invention is not limited, and is preferably evaporation, _ coating (_ (7) such as (10), casting method, bar code, roller coating method (7), etc.; the second electrode used in the present invention is not limited, (5)

An ink jet printing or priming method is formed on the first electrode; the film forming method of the organic electroluminescent material is not limited, and is preferably a vacuum evaporation method or a molecular line evaporation method (MBE> ;, immersion method, spin coating method 18 1268951 is formed by evaporation method; and the first electron beam coating method (E_gun) or sputtering method (sputtedng), the material of the two electrodes is not limited, preferably a conductive material such as aluminum, aluminum lithium alloy, calcium, magnesium silver alloy, silver alloy or silver. , " Since the organic electroluminescent material according to the present invention is as in the above general formula (1)

The mouth w, and the introduction of a hydrazine-substituted group, thereby making the hydrazine-substituted group stable to the adjacent double bond, so when the organic electroluminescent material of the present invention is sublimed at a low pressure and high temperature, it is not easy to = the knife is released In other words, the organic electroluminescent material of the present invention has the same thermal stability. In summary, the organic electroluminescent material 10 t of the present invention and the organic electroluminescent device thereof can effectively enhance the brightness of the light, increase the light efficiency and improve the thermal stability, and at the same time increase the use of the component. [Embodiment] In order to enable the reviewing committee to better understand the technical contents of the present invention, a preferred embodiment of the present invention will be described below. The synthesis scheme of the first embodiment and the compound 4 of the vapor method, and the following flow chart show that the synthetic compounds of the compound 4 of the present invention sequentially synthesize the compounds (A), (B), (C) and (D), respectively. (E) representing compound 4 of the present example: 19 1268951

Compound (4): 2,5-diiodo],4-didecylbenzene (2,5-diiodo-l,4-xylene) taken from moth (27.5 g, 121 mmo 1) and moth (60.25 g, 237 mmo) 1) 5 into a double-necked flask (1 〇〇〇ml), one end of the double-necked bottle is connected to the condensing tube, and the other end of the double-necked flask is sealed with a serum plug; acetic acid (5 〇〇ml) is added, carbon tetrachloride (100 ml), p-terephthalic acid (37. 4 ml), and 3〇0/〇 sulfuric acid water-soluble solution (34 ml), and put a magnet stirrer and stir to 8 (rc; after 28 hours of reaction) The round bottom bottle was iced, and then about 100 ml of sterol was added to stir. 10 solids were precipitated in large amounts, and the solution was removed by suction filtration; the solid was dissolved in chloroform, and the organic layer was collected by washing with saturated aqueous sodium thiosulfite solution. And - the water was removed with anhydrous magnesium sulfate, and concentrated with a vacuum rotary concentrator; recrystallized from EtOAc (1 mL) and methanol (15 mL) to give a white solid (8i 57g), yield 77% The spectral data are as follows: 20 1268951 mp 92〇C -93〇C ; 1H NMR (300 MHz 5 CDC13) δ 2.32 (s5 6H), 7.63 (s, 2H) Also—he do not (B): 2,5_ Bis-trimethyl hydrazine-i,4-dimethylbenzene 5 (2 ,5-bis(trimethylsilyl)-l,4-xylene) Compound (A) (30 g, 83.8 mmol) was placed in a double-necked flask (250 mi), and the addition funnel was placed on the right side.丨75 ml ), use a magnet to disturb the faller; remove the round bottom flask to 0 °C, add 1 · 6 Μ dissolved in the positively simmered smoldering clock (108 ml, 0 · 17 mol) in the addition funnel Slowly instill 10 drops and mix thoroughly; after half an hour, inject gasified triterpenoids (32.4 ml, 250 mmol) and ether (70 ml) into the addition funnel, slowly instill; reaction for three hours After that, the reaction mixture was poured into a conical flask containing an aqueous solution of sodium hydrogencarbonate, and neutralized, and extracted with ethyl acetate several times. The organic layer was collected, water was removed with anhydrous magnesium sulfate, and solvent was removed by vacuum concentrator Recrystallization from decyl alcohol 15 gave a white solid (10.50 g), yield 50%. The spectral data is as follows: mp 68 〇 C - 69 〇 C ; 1H NMR (300 MHz, CDC13) δ 0.30 (s, 18H) ,2·41 (s,6H),7·22 (s,2H) 20 t compound (C): M-bisdidecyl bromide-2,5-bistrimethylantimonybenzene (1,4-Bis (bromomethyl)-2,5_bis(trimethylsilyl)benzene) Compound (B) ( 7.00 g, 28.0 mmol), N-bromosine lactam (NBS) (9.97 g, 56.0 mmol) and benzoyl peroxide (75%, 0.678 g, 2) · 1 mmol) in a two-necked flask (250 ml) 25, one end of the double-necked flask connected to the condenser, nitrogen gas, the other end sealed with serum plug 21 1268951; injected with carbon tetrachloride (72 ml), magnet Stirring with a stirrer; heating to 50-60 ° C, and illuminating with a halogen lamp, stopping the reaction after four hours; after returning to room temperature, gravity filtration, rinsing the solid with a small amount of carbon tetrachloride, and collecting the filtrate; The aqueous solution of saturated sodium thiosulfite and aqueous sodium chloride solution was washed several times, and the aqueous layer and the organic layer were separated, and the aqueous layer was extracted with ethyl acetate; the organic layer was collected, dried over anhydrous sulfuric acid, and then removed by vacuum concentrator > The granules were recrystallized from decyl alcohol to give a white solid (8 · 19 g) in a yield of 72%. The spectral data are as follows: mp 92 〇C -93 〇C ; 1H NMR (300 MHz, CDC13) δ 0.39 (s? 10 18H), 4.60 (s, 4H), 7.52 (s5 2H) [compound (D): 1 ,4-bis-diethyl-2,5-bis-trimethylsulfonium-benzene-1,4-dimethyl sulphate (1,4-Bis(diethyl)-2?5-bis(trimethylsilyl)-phenyl -l 34-dimeth 15 anephosphonate) Take compound (C) (4_00 g, 9·80 mmol) and Triethyl phosphite (3.70 ml, 21.6 mmol) in a two-necked flask (25 ml) and stir with a magnet stirrer. Heated to ll 〇 ° C under nitrogen, refluxed for 24 hours; warmed to room temperature, and then vacuum-dried to give a white solid; isolated and purified by silica gel column chromatography 20 (distillation: ethyl acetate / hexane = 2 ), finally a white solid (4.30 g) was obtained with a yield of 84%. The spectral data are as follows: mp 65 〇C -66 〇C ; 1H NMR (300 MHz 5 CDC13) δ 0.33 (Sj 18H), 1.19 (t, J = 7.02 Hz, 12H), 3.25 (d, J = 20.8 Hz, 4H ), 3.95 (m, 8H), 7.60 (s, 2H) 22 25 1268951 Compound (E) : 1,4-bis(4-(N,N-diphenylammonio)styryl-2,5_ 1,3,4-di(4-(N,N-diphenylaminophenphen)vinyl-2,5-di(trimethylsilyl)benzene) Compound (D) (0.800 g, 1.731 mmol·) 4-(N,N-diphenylammonium) 5 benzofural (0.907 g, 1.731 mmol) was placed in a double-necked flask (25 ml). The neck of the flask was filled with nitrogen and the other end was sealed with serum. Ingestion; inject THF (5.2 ml), stir with a magnetic stirrer for 30 minutes; add t-BuOK (0.5 83 g, 5.193 mmol) in an ice bath, the color of the solution immediately turns yellow; return to room temperature and continue stirring for 24 hours. Under an ice bath, a 5% aqueous solution of sulfuric acid was added to the mixture, and the mixture was filtered under suction to collect a yellow solid, which was recrystallized from toluene to give a pale yellow solid (0.936 g), yield: 85%. The spectral data is as follows: mp 296〇C 6-297〇C ; 1H NMR (400 MHz, CDC13) δ 0.38 (s,18H),6.91 (d,J = 8 Hz, 2H), 7.01 (d, J = 8 Hz, 4H), 7.05 (d, J = 7 Hz, 4H), 7.10 (d, J = 7 Hz, 8H), 7.22-7.31 (m, 15 10H) ), 7.36 (d, J = 8 Hz, 4H), 7.78 (s, 2H) Please refer to the synthesis method of the compound (E). Compound 3: 1,4-double (mouth-chelating-9-yl) styryl group 2,5-bis-trimethylsilylbenzene-l-(4-(carbazol-9-yl)phenyl)vinyl-2,5-di(trimethylsilyl)benzene)

The spectral data are as follows: mp 382t-385°C; NMR (400 MHz, CDC13) δ 0.50 (s, 18H), 7.10 (d, J = 1268951 8 Hz, 2H), 7.32 (dd, J = 6.4, 1.6 Hz, 4H), 7.38~7.52 (m, 8H), 7.56~7.63 (m, 6H), 7.75 (d, J = 8.6 Hz, 4H), 7.91 (s, 2H), 8.16 (d, J = 8.0 Hz, 4H 5) Compound F: 1,4-bis(4-(N,N-naphthalen-1-yl-phenylammonio)styryl-2,5-bistrimethyl lysine-benzene (1,4 -di(4-(N,N-Naphthalen-1 -yl^henylamino)phenyl)vinyl-2,5-di(trimethylsilyl)benzene)

10 Spectral data are as follows: mp 296 〇C6-298〇C; 1H NMR (400 MHz, CDC13) δ 0.37 (s3 18H), 6.87 (d, J =8.4 Hz, 2H), 6.94 (d, J = 6.4, 1 · 6 Hz, 2H), 6.98 (d, J = 8 · 4 Hz, 4H), 7.08 (d, J = 8.6, 8.0 Hz, 4H), 7.18 to 7.24 (m, 4H), 7.27 to 7.38 (m, 10H), 7.46 (dd, J = 8.0 Hz, 4H), 7.76 (s, 2H), 7.77 (d, J = 7.8 Hz, 2H), 7.88 (d, J = 8.0 Hz, 2H), 15 7.93 (d , J=8.0 Hz, 2H) Example 2, Organic Electroluminescent Light Element First, a glass substrate of 100 mm×100 mm is provided, and then a 150 nm thick indium tin oxide is deposited on the glass substrate, and yellow 20 Light# After forming a pattern of 10mm X 10mm light-emitting area, vacuum evaporation is performed under vacuum degree 1 (T5 Pa, the first layer is first plated with 35nm thick hole transmission material, and the hole transmission material is NPB (N , N'-diphenyl-N, N'-bis-(1 -naphthalenyl)-[l,1 '-biphenyl]-4,4'-diamine), the structure of which is shown below, the evaporation rate of the hole transport material The system is maintained at 0.2 nm/sec. 25 Next, the second layer is simultaneously plated with the following DNA (9,10-Di-naphthalen-2-yl-anthracene And the organic electroluminescent material of the present invention (ie, the compound (E) of the first embodiment) is a light-emitting layer, and the weight ratio of 1268951 dna to the compound (E) is 100:1·7, and the thickness thereof is 45 nm, and the steaming rate is The system is maintained at 0.2 nm/sec.

NPB

5

Then, the third layer was plated with AlQ3 (tris(8-quinolino)aiuminum) having the structure shown below as an electron transport layer having a thickness of 2 Å and an evaporation rate of 0.2 nm/sec.

After that, LiF (1.2 nm) and Al (150 nm) were used as materials for the above-mentioned electric sub-transport layer to serve as a cathode. Thus, the organic electroluminescent device according to the preferred embodiment of the present invention is completed. Embodiment 3 Comparative Example When the organic electroluminescent device is a compound of the following formula (II) as the material of the light-emitting layer, when a voltage of 6 V is applied to the obtained organic electroluminescent device, The luminance ccj/m2, the current density was 21.9 mA/cm2, the luminous efficiency was 2.4 lm/W, and 4·6 Cd/A, αΐ·Ε·=(〇·ΐ5, 0.20). 25 1268951

When the organic electroluminescent device uses another conventional organic electroluminescent material as shown in the following formula (III) as a material of the light-emitting layer, when a voltage of 6 V is applied to the obtained organic electroluminescent device, The luminance was 5 1 〇 16 cd/m 2 , the current density was 11.5 mA/cm 2 , the luminous efficiency was 4.6 lm/W and 8.9 cd/A, and CIE_= (0.16, 0.27).

Embodiment 4 Measurement Results 10 The luminescence characteristics of the organic electroluminescence device of the present invention are measured by using a direct current (DC) voltage to drive an organic electroluminescence element, and measured by Keithly 2〇(9), and the result shows that the luminescence color is blue. color. In addition, the EL diaphragm g of the organic electroluminescence element is measured by a spectrometer of 〇tsuka Electronic Co., and the photodiode array is used as a detector, and the measured spectral pattern 15 is as shown in FIG. The emission wavelength is 468 nm, and the current-luminance value (IB) of the organic electroluminescence element is as shown in Fig. 2. The current-voltage value (I_v) is as shown in Fig. 3. Therefore, when a voltage of 6 V is applied When the organic electroluminescence device is obtained, a luminance of 1943 cd/m2, a current density of 21 2 mA/cm2, a luminous efficiency of 4·8 lm/W, and 9.2 cci/A, CI E = (() 18, 20 can be obtained. 0.32). 1268951 Comparing the above results, it can be clearly understood that the organic electroluminescent material of the present invention is superior to the conventional ones in terms of maximum brightness or luminous efficiency. An organic electroluminescent device 5 element as shown in the formula (II) or (III). The above embodiments are merely exemplified for convenience of explanation, and the claimed scope of the invention is self-explanatory. The invention should be limited to the above-mentioned embodiments, and any equivalent modifications or changes to the K?= line should be included in the following. The scope of the patent [simplified description of the drawings] 15 20 shows the EL spectrum measurement chart of the preferred embodiment of the present invention and the conventional organic electroluminescent device; the electro-excited material first Figure 2 shows the comparison of the present invention A current-luminance measurement diagram of a preferred embodiment and a conventional organic electroluminescent device. (Excitation Light Material FIG. 3 shows a preferred embodiment of the present invention and a conventional current-voltage of an organic electroluminescent device. Measurement chart FIG electroluminescent material [27] Number Description

Claims (1)

... The broken axe paste repair (|6 original pick, patent scope: 1. An organic electroluminescent material, including a formula below: structure: work,) 5 wherein R1, R2, and R3 are independently substituted or unsubstituted alkyl groups having 1 to 10 carbon atoms, and substituted or unsubstituted cycloalkyl groups having 3 to 1 carbon atoms. a substituted or unsubstituted alkyloxy group having from 1 to 1 carbon atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 3 carbon atoms, or a substitution of 6 to 3 carbon atoms or not a substituted or substituted arylalkyl group having 6 to 3 carbon atoms; R 4 and R 5 are each independently substituted or unsubstituted with 1 to 1 carbon atom; An alkyl group, a substituted or unsubstituted cycloalkyl group of 3 to 1 carbon atoms, a nitrile group, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 3 carbon atoms, aroma a complex ring group 15 , a group; Ar is an aromatic hydrocarbon group, thiene (thi〇phene), furan (furan) or an aromatic complex ring group, and Ar is substituted or unsubstituted having 6 to 3 carbon atoms An aromatic smoki group or an aromatic complex ring group, and thiene (thi phene), σ furan (furan), A and B are independent hydrogen atoms, having 1 to 1 a substituted or unsubstituted alkyl group of one carbon atom, a 20- or unsubstituted cycloalkyl group having 3 to 1 carbon atoms, a substituted or unsubstituted alkenyl group having 1 to 1 carbon atom, a substituted or unsubstituted aromatic having from 6 to 30 carbon atoms 28 1268951 known as an ethyl group, a substituted or unsubstituted aromatic fluorenyl group having 6 to 30 carbon atoms or a substitution having 6 to 30 carbon atoms or Unsubstituted aralkyl. 2. The organic electroluminescent material according to claim 1, wherein the compound of formula (I) has a bond or no bond with A or B, and a bond between A and B or There is no key knot. 3. The organic electroluminescent material as described in claim 2, wherein the material is arbitrarily selected from the group consisting of the following substituent groups: And R6 and R? are each independently, having 1 to 1 carbon atom, 10 or unsubstituted alkyl groups, 6 to 30 carbon atoms, substituted or unsubstituted aromatic hydrocarbon groups, aromatic complex cyclic groups Or aralkyl. 4. The organic electroluminescent material according to claim 1, wherein the material is any one selected from the group consisting of: 29 1268951 Compound 9 Compound 11 30 1268951 5. The organic electroluminescent material as described in claim 1 31 1268951 wherein the material shown in formula (i) is a dopant of the light-emitting layer. 6. The organic electroluminescent material according to claim 5, wherein the doping concentration of the material shown in the formula (I) is between Klwt% and 3〇%. 7. The organic electroluminescent device comprises at least: a dipole, an organic electroluminescent layer and a second electrode are sequentially disposed on a substrate; The material used in the organic electroluminescent layer comprises a compound of the following formula (1): And Ri, R2, and Rs are each independently substituted or unsubstituted alkyl group having 1 to 1 carbon atom, or substituted or unsubstituted cycloalkylky group of 3 to 1 carbon atom. a substituted or unsubstituted alkoxy group (alkyl0Xy) having a carbon atom, a substituted or unsubstituted 15 atomic group having 6 to 3 carbon atoms, or a substitution of 6 to 30 carbon atoms or not a substituted aromatic or a cyclyl group, or a substituted or unsubstituted aralkyl group of 6 to 30 carbon atoms; R 4 and R 5 are each independently substituted or unsubstituted alkyl group having 1 to 1 carbon atom, A substituted or unsubstituted cycloalkyl group of 3 to 10 carbon atoms, a nitrile group, or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 carbon atoms, an aromatic 20 fluorenyl group or an aralkyl group · Ar is an aromatic hydrocarbon group, thiene (thi〇phene), furan or aromatic complex ring group, and Ar is a substituted or unsubstituted aromatic hydrocarbon group or aromatic complex having 6 to 3 carbon atoms. a ring group, and thiophene 32 1268951 (thiophene), furan (furan); a and B separate hydrogen atoms, with 1 to 10 carbon atoms a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, a substituted or unsubstituted chain group having from 1 to 10 carbon atoms, having 6 to 3 units a substituted or unsubstituted 5 aromatic radical of a carbon atom, a substituted or unsubstituted aromatic complex cyclic group having 6 to 30 carbon atoms, or a substituted or unsubstituted aralkyl group having 6 to 30 carbon atoms . 8. The organic electroluminescent device according to claim 7, wherein in the compound of the formula (I), the Ar system has a bond or no bond with the B or B, and a bond between A and B or There is no key knot. Wherein the material is arbitrarily selected from the group consisting of the following substituent groups: 0. The organic electroluminescent device according to claim 7, The heart and the I system are independent and have 1 to 1 carbon atoms. 33 1268951 A substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic hydrocarbon group of 6 to 30 carbon atoms, an aromatic complex ring group, or an aralkyl group. The organic electroluminescent device described in claim 7 of the patent scope wherein the material is any - is selected from the group consisting of the following compounds: 34 1268951 35 1268951 The organic electroluminescent element and the intermediate compound described in item 7 of the profit-seeking range are doped in a hole transport layer. 5 & ιφφ Patent 帛 帛 11 彳 胄 胄 胄 ; ; ; ; 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 、 中 中 中 中 中 中 中 中 中 中 中 中 中 、 、 、 中 、 An aromatic diamine compound or an aromatic triamine compound, and the glass transition degree of the hole transport layer is greater than 100 ° C. The organic electroluminescence element of the invention of claim 7, wherein the substrate is a transparent substrate. 14. The organic electroluminescent device of claim 7, wherein the first electrode is a transparent electrode. 15. The organic electroluminescent element according to claim 7, wherein the organic electroluminescent layer sandwiched between the first electrode and the second electrode has a laminated structure of one or more layers. The organic electroluminescent device of claim 15, wherein the laminated structure comprises a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer, and combinations thereof. 17. The organic electroluminescence element 5 according to claim 15 wherein the layered structure is formed by evaporation, spin coating, inkjet printing or printing ( The printing method is formed on the first electrode. 18. The organic electroluminescent device according to claim 7, wherein the film forming system of the material used for the organic electroluminescent layer is vacuum vapor deposition 10, molecular line entanglement (MBE), immersion method, A spin coating method, a casting method (castmg), a bar code method, a roll coating method, or the like is formed. 19. The organic electroluminescent device according to claim 7, wherein the first electrode is formed by a vapor deposition method, an electron beam mirror method (e_(four) or 15 sputtering). The organic electroluminescent device of claim 15 is characterized in that the material of the first electrode is aluminum, aluminum lithium alloy, calcium, magnesium silver alloy, silver alloy or silver conductive material.