TWI309672B - Red electroluminescent compounds and organic electroluminescent device using the same - Google Patents

Description

<1309672 IX. Description of the Invention: [Technical Field] The present invention relates to an organic electroluminescent compound as shown in the following Chemical Formula 1, a method for producing the same, and an organic electroluminescent compound as an electroluminescent material. Electroluminescent element: [Chemical Formula 1]

[Prior Art] The most important factor in the development of high-efficiency and long-life organic electroluminescent elements is the development of high-efficiency electroluminescent materials. In fact, in terms of the development of electroluminescent materials, red or blue electroluminescent materials have relatively low luminescent characteristics compared to green electroluminescent materials. There are three electroluminescent materials (i.e., red electroluminescent materials, green electroluminescent materials, and blue electroluminescent materials) for full color display, and thus the lowest of the three materials determines the display efficiency of the entire panel. Therefore, the development of high efficiency and long-term use of blue light or red electroluminescent materials is a key issue for the improvement of the characteristics of all organic electroluminescent elements. It is currently known that the color purity and luminance of red electroluminescent materials have not reached a satisfactory level. For most materials, the main use of the dopant system is that it is difficult to construct a high-efficiency electroluminescent device using a high-concentration thin layer because of the concentration extinction effect between the same red photoluminescence molecules. That is, the farther the intermolecular distance is, the more favorable the luminescent characteristics are. By the same token, it has not been easy to borrow 1309672 to obtain high efficiency red illumination characteristics by reducing the color sensitivity in the range of wavelengths greater than 630 nm pure red. Therefore, it is possible to develop a red photoelectroluminescent material which is highly efficient and can be used for a long period of time, if only red electroluminescent molecules are avoided and the emission wavelength can be shifted to a larger wavelength than the current range. Among the red electroluminescent materials, derivatives of DCM2 (4-(dicyanoindol)-2-mercapto-6-(julolotyl-9-enyl)-4 and - sulfonium) are known in luminance. And color purity is very good. In an academic study on the above-mentioned DCM2 derivative for reducing the concentration extinction effect of red electroluminescent materials, a method of utilizing bulky substitution radicals to minimize the use of molecules has been known.

CH Chen of Eastman Kodak proposed a DCJTB (4-(dicyanomethyl)-2-tert-butyl-6-(1, which shows the best efficiency among red electroluminescent materials). 1,7,7-tetramethyljulipodine ("111110" 1)-9-alkenyl)-4)7-anthracene). The material has hydrazine (: a few (4-(dicyanoindole)-2-methyl-6-(1,1,7,7-tetradecyl-julidolodine (]111丨1〇471)-9- Alkenyl)-4 and -pyranyl) are identical to the concept of placing a bulky (131111^) substituent. In the case of DCJTB, not only the internal extinction effect is seen because the methyl group of DCJT in the material is converted to the monobutyl group. And it quickly decreases, and it also proves that DCJTB has a significant improvement in wavelength or luminance. 7 Ί309672

DCJTB

Also proposed is a kind of DCJTI (4-(dicyano-anthracene)-2-isopropyl-6-(1,1,7,7-tetradecyl-julilodyl) in the same group. -9-Alkenyl)-4H-purpurin) wherein the thiol group in DCJT is converted to isopropyl.

DCJTI At the same time, the inventors of the present invention developed a high-efficiency red electroluminescent material by using conventional 4-(dicyano-anthracene)-6-(1,1,7,7-tetradecyl-julidolodine ( Ju 1 i 1 ody 1)-9-binding)-4H-° Position 2 of this ruth is disposed in a bulky substituent such as adamantyl, 4-pentylbicyclo[2,2,2] An octyl group (a type of fused ring) having suitable luminescent characteristics is disclosed in Korean Laid-Open Patent Publication No. 2004-93679. SUMMARY OF THE INVENTION The present inventors have made efforts to develop an electroluminescent material having excellent luminescent properties compared to conventional red electroluminescent materials. The inventors understand that high-efficiency red electroluminescent materials can be developed by: (i) avoiding the use of electroluminescent molecules and (ii) grafting concepts: making the electroluminescent material emit light 8 130^672. 'Become the design of electroluminescent material molecules, and use the jullil Qdyl which is already part of the t body to be an electron acceptor. The extreme performance induced by the influence of the shovel. Based on this, by the specific position of the julilodyl which will cause the stereotype_substitute_substitute to be placed in the electronic=partial part, the development of the traditional red light series (4) has a better hairline sign. The electroluminescent material has a very high density even at a high concentration and provides one using the above

Accordingly, it is an object of the present invention to provide an electroluminescent device of a red photoelectroluminescent compound electroluminescent compound which is excellent in luminous efficiency. [Embodiment] The present invention relates to an organic electroluminescent compound which is manufactured as an electric ant light-emitting element using these organic electroluminescent compounds as electroluminescent materials. In the case of melting, the organic electroluminescent compound of Ming Dynasty has a three-dimensional barrier effect due to the steric barrier effect, which has a reinforcing structure of 1% of the Julilot base and has a polar structure in the application of the knife; And, oh, the energy that is significantly increased by the efficient energy transfer mechanism. DCJTB, which is generally a red fluorescent material, has a disadvantage of not being rotated because of the current during the doping to the main illuminant (ie, the carrier, the luminescent dopant molecule is limited, and the luminescence is reduced. The rate &gt;, :ee) is lowered as the amount of charge flowing through the entire element is lowered. Please note that the inventors have substituted the alkyl group by the insertion of a decyl group or an alkyl fluorenyl group by placing a functional group capable of adding conductivity into the dopant. Meanwhile, the red photoelectroluminescent compound of the present invention or the W and R6 compound is bonded to the alkylene group of C3-C5 to form a ring-shaped compound which is not the same as those of the formulas 3 and 4, and which are independent of each other, Ri&amp;R5 or π and fluorene. [Chemical Formula 3] R6 R4

[Chemical Formula 4]

Wherein the substituents R2, R3, R4, R6 and R7 are the same as those shown in the chemical formula 1 or 2, and A may independently be -CH2-, -CH2CH2-, -CH2CH2CH2_; and the ring of the ring includes 'A' among them - A carbon can be formed into a fused stone. The exemplified Wei Laiji includes, for example, dimethyl (tetra) ring sister 'ethyl methyl pour ring money, diethyl shi xia Cycloheptane, diphenyl wei ring oxime, dimethyl wei ring octane, diethyl decane ring Octane, diphenylnonane cyclooctane, etc., and ... and γ are bonded to a helical ring of C4_Ci〇-decane cyclopentane, decane cyclopentene and decane cyclooctane. The above decane cycloalkane of Chemical Formula 3 or 4 includes the following Chemical Formula 5 or 13 1^09672

[Chemical Formula 8]

Wherein R3, R4, R5, R6, R7, R8, and R9 are the same as those shown in Chemical Formula 2. Meanwhile, R8 and R9 may both be -CN, as shown in Chemical Formula 3-6, or form a 1,3-indanedione ring together with g, and further a compound represented by Chemical Formula 9 in the following 0: [Chemical Formula 9 ]

15 1309672 R4

Compound Ri r2 H3 tv Rs Re Rv 218 \/Si(i-Pr)3 H -CH3 -ch3 HH 220 \^Si(Ph)3 H -CH3 -CHa HH ^VCsH" 222 ('^/Vc5h11 -CHs - CHs -CHs HH n-CgHn 224 -CHs -CHs HH 226 -CHs -CHs -ch3 HH 228 , /Si(CH3)3 H -CH3 -CH3 HH , ΛηΌ5Η" 230 \^Si(CH3)3 -Si(CH3 ) 3 -CH3 -CHs HHW^n-CsHu 236 —Q&gt;-Si(CH3)3 _CH3 -CH3 -ch3 HHW^n-C5Hii 238 Si(Ph)3 - CH3 -CH3 -CH3 HHW^n-CsHn 17 1309672

Compound Ri r2 R3 R4 Rs He Ry 240 \^Si(Ph)3 H , ^Si(Ph)3 HHH 246 ~Si(i-Pr)3 -CHa -CHa -CHa HH 248 Si(CH3)3 -CHa - CHa -ch3 HHW^n-CsHn 250 \^Si(CH3)3 H ^Si(CH3)3 HHH WNn-C5Hn 252 -CHs -ch3 HH η-〇5Η-(·( 256 \^Si(CH3)3 ~ a(CH3)3 -CHs -ch3 HH 258 -CHs -CHs -CHa -ch3 \^Si(CH3)3 HW^n-C5Hn 294 H -ch3 -ch3 HH 296 H -CH3 -CH3 HH Tert-butyl 302 - Si(CH3)3 \^Si(CH3)3 -CHa -CH3 HH 304 -Si(CH3)3 \^Si(CH3)3 -CHs -CHs HH 18 '1309672.

Compound Ri R2 R3 Ri R. R6 R? 306 -Si(CH3)3 \zSi(CH3)3 -ch3 -CH3 HH -〇-卿308 -Si(CH3)3 \/Si(CH3)3 -ch3 -CH3 HH h3c ~h^-ch3 h3c 310 -Si(CH3)3 \xSi(CH3)3 -ch3 -ch3 HH Tert-butyl 218T \^Si(i-Pr)3 H -ch3 -CHs HH Tert-butyl 220T \ /Si(Ph)3 H -CHa -CHa HH tert-butyl 222T W^n-CjHn -ch3 -CH3 -CH3 HH tert-butyl 224T R1 -ch3 -CH3 HH tert-butyl 226T -ch3 -CHa. -CH3 HH Tert-butyl 228T \^Si(CH3)3 H -ch3 -CH3 HH tert-butyl 230T \zSi(CH3)3 -CHa -CHa -CHs HH tert-butyl 236T -^^~Si(CH3)3 -ch3 - CHs -CH3 HH T-butyl 19 1309672

Compound Ri r2 Rs R4 Rs Re R? 238T \/Si(Ph)3 -CHs -ch3 -ch3 HH Tert-butyl 240T \/Si(Ph)3 H \^Si(Ph)3 HHH Tert-butyl 246T \^ Si(i-Pr)3 -CHs -CH3 -CH3 HH Tert-butyl 248T \^Si(CH3)3 -CHs -CH3 -CH3 HH Tert-butyl 250T \^Si(CH3)3 H \^Si(CH3) 3 HHH tert-butyl 252T -CH3 -CH3 HH tert-butyl 256T ^Si(CH3)3 ~Si(CH3)3 -CH3 -CH3 HH tert-butyl 258T -CHs -Clh -CH3 - CH3 V-Si(CH3b H Tert-butyl 294T H -ch3 -CHs HH tert-butyl 218A ^SiC.-Pr)3 H -CH3 -CHs HH 220A \/Si(Ph)3 H -CHs -CH3 HH 20 1309672

Compound Ri r2 R3 R4 13⁄4 Re R7 222A -ch3 -ch3 -CH3 HH 224A R1 % -CH3 -ch3 HH 226A -CHa -CHs -ch3 HH 228A \zSi(CH3)3 H -CH3 -CH3 HH 230A •^Si( CH3)3 -Si(CH3)3 -CHs -CHs HH 236A -^^-SKCH3h -CHa -CH3 -CHs HH 238A \^Si(Ph)3 -ch3 -ch3 -CIi3 II H 240A \^Si(Ph&gt; 3 H \^Si(Ph)3 HHH 246A \/Si(iP〇3 -CHa -ch3 -ch3 HH 248A ^Si(CH3)3 -ch3 -ch3 -CH3 HH 21 1309672

Compound Ri r2 Rs R4 Rs Re Rv 250A \^Si(CH3)3 H \^Si(CH3)3 HHH 252A -CHa -ch3 HH 256A \/Si(CH3)3 \_/Si(CH3)3 -CHs - CHa HH 258A -CHs -CHa -CHa -CHa ^^Si(CH3)3 H

[Table 2]

22 1309672

Compound Ri R2 Ha Hi* r5 Rc r7 270 -Si(CH3)3 \/Si(CH3)3 -CHs -CH3 HHW^n-CsHu 312 •Si(CH3)3 \^Si(CH3)3 -CHa -CHa HH 314 -Si(CH3)3 ^/Si(CH3)3 -CHs -CHa HH 320 -Si(CH3)3 \^Si(CH3)3 -CHa -CH3 HH Tert-butyl 219T \zSi〇-P〇3 H -ch3 -CHs HH tert-butyl 239T \/Si(Ph)3 ~Clh -ch3 -ch3 HH tert-butyl 241T \/Si(Ph)3 II \/Si(Ph)3 HHH tert-butyl 247T \/ Si(i-Pr)3 -ch3 -ch3 -CHa HH Tert-butyl 249T \^Si(CH3)3 -CHa -CHs -CHa HH Tert-butyl 251T \/Si(CH3)3 H Si(CH3)3 HHH Tert-butyl 23 * 1309672.

Compound Ri r2 Ra R4 Rs Re Rt 219A \/Si〇-Pr)3 H -ch3 -CH3 HH 239A ^Si(Ph)3 -CHa -ch3 -ch3 HH 241A ^SKPhh H \^Si(Ph)3 HHH 247A \/Si(i-Pr)3 -CH3 -ch3 -CHa HH 249A i(CH3)3 -CHa -CH3 -ch3 HH 251A \^Si(CH3)3 H \^Si(CH3)3 HHH

[Table 3] 24 * 1309672

Compound A r2 Ra R4 Re Ry 234 -CH2CH2- -CH3 -ch3 -CH3 HW^n-CsHu 234T ~CH2CH2_ -CHS -CH3 -CH3 H Tert-butyl 234A -CH2CH2- -CH3 -CH3 -CH3 H 254 ~CH2~ -CHs -ch3 -CH3 H &lt;J^n-C5Hu 254T -CH2~ -CH3 -ch3 -CH3 H tert-butyl 254A -CH2~ -CH3 -CH3 -CH3 H 260 , ~CH3 /si〇T -CH3 - Ch3 -CH3 HW^n-CsHu 260T N ^CH3 /si〇r -CH3 -ch3 -CH3 H tert-butyl 260A /si〇T -CH3 -CHS -CH3 H 25 * 1309672

Compound A r2 R3 R4 R6 R? 235 -CH2CH2- -ch3 -ch3 Rf^ WVCsH" 235T -CH2CH2- -CH3 -CH3 Tert-butyl 235A -CH2CH2- -CH3 -CHs 255 -CH2- -CH3 -CH3 r4_&gt; R6 ^ ^Λη-CsHn 255T -ch2- -CH3 -CH3 Rk^&gt; Tert-butyl 255A -CH2- -CH3 -CH3 261 /si(J -CH3 -ch3 R4' /^CH3 ReXT 261T /si〇T -CH3 -ch3 tert-butyl 261A, wide ^ch3 /si〇T -CH3 -CH3 R6-^ VJ

[Table 4] 26 * 1309672

Compound A r2 R3 R4 Re r7 334 -CH2CH2- -ch3 -ch3 -ch3 H 334T -CH2CH2- -CHs _ch3 -ch3 H tert-butyl 334A -CH2CH2- -ch3 -ch3 -ch3 HA 354 _CH2 - -ch3 -ch3 - CH3 H 354T -ch2- -ch3 -ch3 -ch3 H tert-butyl 354A -ch2- -ch3 -CHs -ch3 H 0J 360 &gt;σ -ch3 -CHs -ch3 H 360T /CH, XT -ch3 -ch3 -ch3 H tert-butyl 360A ch3 XT -ch3 -ch3 -CHs H ά 335 -CH2CH2- -ch3 -CHs A 27 '1309672 Compound A r2 R3 R4 丨1 r7 335T -CH2CH2- -ch3 -ch3 A tert-butyl 335A -CH2CH2 - -ch3 -ch3 4 355 -ch2- _ch3 -ch3 355T -ch2- -ch3 -ch3 tert-butyl 335A -ch2- -CH3 -ch3 4 361 ~/CH3 &gt;σ -CH3 -ch3 X 361T ~/CH3 &gt ;σ -CH3 -ch3 r6--sU tert-butyl 361A ~/Η3 XT -CH3 -ch3 -4 ^CH- :〇σ 0k For the method for producing red electroluminescent compound of the present invention, please refer to the following chemical reaction formula 1-3 Shown. The chemical reaction formula 1 shows a reaction step for producing a Julilotyl derivative in which the Julilotyl derivative is an electron donor moiety of the compound of the present invention. [Chemical Reaction Formula 1] 28 • 1309672

i Aniline (1>, a starting material, together with a mixed solution of 1 in benzotriazole-methanol or Benghis dipyridin and methacrylate, dehydrogenated in a DeanStark reaction to obtain a clumpy triazolium substitution The aniline (2) 'and then the tetrahydroquinoline derivative (4) is obtained via a ring formation reaction according to the Friedel-Crafts alkylation reaction between the aniline derivative (2) and the hydrocarbon-dilute derivative (3). The formation reaction is preferably carried out by the catalysis of SnCh at a low temperature of about -78 ° C. The substitution of the remaining nitrogen of the tetrahydroquinoline derivative (4) with a clumpy triazolium is obtained. The tetrahydroquinone derivative (5) # after the oxime-substituent is obtained by the previous Friedeb Crafts reaction (7), and the above compound is reacted under the conditions of p〇Ch/DMF. 7), obtaining a derivative of Julilotdin aldehyde (8). If it is desired to produce a Julilotyl derivative (wherein RkR3, and R5=R6)' can obtain a bis(phenylenetrienyl) stupylamine from aniline ( g) after reacting the hydrocarbon olefin derivative (3) as shown in the following chemical reaction formula 12: [Chemical reaction formula 12] 29 Ί309672

Bt = benzotriazole group Next, the method for producing the quinone derivative (16) or (18) (electron donor portion) of the present invention can be referred to the following chemical reaction formulas 2 and 3: [Chemical Reaction Formula 2]

As shown in the chemical reaction formula 3, when the oxime derivative is produced, the ketone-based ketone-based diketone compound (13) is passed through ethyl acetate methyl acetate (η) and the ketone derivative (12) under alkaline conditions. It is formed by means of a ketone protecting group. Any base generally used can be used as the base in the above step, but it is preferred to use a bulky test such as LDA, bis(trimethylmethane alkyl)sodium decylamine (NaN(;TMS)2) or the like. The appropriate reaction temperature is selected depending on the nature of the base used. The deprotection reaction and the ring formation reaction of the triketone compound (13) thus obtained are carried out in an acidic solution, and then the oxime derivative (14) is reacted with malononitrile (15) under acidic or basic conditions to obtain An electron acceptor moiety of a compound of the invention. At the same time, the reaction of '1,3-indanedione with the oxime derivative (14), in addition to the oxime derivative having a dicyano substituent, can also be obtained with a substituent of 30*1309672. A derivative (18). [Chemical Reaction Formula 3]

The red electroluminescent compound of the present invention is obtained by the above steps as an electron donor moiety of the quinoline aldehyde derivative (8) and an electron acceptor moiety (16) or (18). Reaction under conditions. Alkal which is generally used can be used, but it is preferred to use a weak test such as a bottom bit. [Chemical Reaction Formula 4]

[Examples] The method for producing a red electroluminescent compound of the present invention is exemplified by the following examples, and the method and method for evaluating the characteristics of the red electroluminescent compound of the present invention are also explained below. [Example 1] Synthesis of Compound 256 31 *1309672 [Chemical Reaction Formula 5]

The compound 2 5 6 of the φ standard is synthesized according to the procedure shown in the chemical reaction formula 5. 0.5 g (3.1 mmol) of compound 31 (a tetrahydrononolone derivative) '0.55 g (3.7 mmol) 1H-benzotriazol-1-nonanol and 1.5 g of molecular sieve ( 4 port) was dissolved in 8 ml of THF and heated at 50-60 T: until 1H-benzoquinone tris-l-nonanol was completely dissolved. The heated material was allowed to stand at room temperature for 20 hours. Thereafter, the molecular sieve was sieved and Xing was blown off to obtain Compound 32. Under nitrogen, '34 ml of hydrazinyl lithium (1.6 M, with diethyl ether as solvent) • Slowly add l〇ml dissolved 2-indole-1,3-pentanediyl-parade (trioxane) 33) THF solution. The mixture was stirred at room temperature for 12 hours, and then 10 ml of methanol was slowly added. The mixture was stirred for 1 hr and extracted with diethyl ether to give EtOAc. 0.5 g (3.11 mol) of compound 31, compound 32, and 〇6 g (3.1 mmol) of compound 33 were dissolved in dichloromethane, and at -78.毫升1. 1 ml of SnC14 (1.0 M, using dioxane as solvent). Room 32 1309672 The mixture was stirred for 12 hours under phoenix. The reaction was quenched with a saturated aqueous solution of NaOH (0 ° C), and the mixture was extracted with dioxane to give 35 g of the compound of the compound, and then, under a nitrogen atmosphere, 0.27 ml (2.88 mmol) of 15 〇 (:13 was poured into 2 ml) DMF, and the solution was stirred at room temperature for 1 hour. 2 g (1.92 mmol) of compound 34 was dissolved and added to 3 ml of DMF, and the reaction mixture was stirred at 40 C for 12 hours to saturate NaOH. The solution is terminated with an aqueous solution, and the reaction mixture is extracted with ethyl acetate to obtain a compound of 〇 21 〇 _ 35. 358 g (〇·89 mmol) of compound 35 and 0.3 g (0·89 mmol). Compound 36 was dissolved in 12 ml of ethanol, and 〇·44 ml (4.55 mmol) of piperidine was added to the mixture. Then, the ampoule was filled with a molecular sieve (4 ports) of Dean-Stark trap, and at 120 ° C under nitrogen. The mixture was heated for 7 hours. After 12 hours, the reaction material was cooled to 0 ° C, and the precipitate which formed as a reaction product was filtered, and recrystallized from dioxane and n-octane to obtain 0.42 g (synthetic product). Rate 67 «Standard compound 256. • [Example 2] Synthesis of compound 248 [Chemical reaction Should be 6]

33 1309672 The title compound 248 was synthesized by the procedure shown in Chemical Reaction Scheme 6. 0. 5克 (3.1 mmol) of Compound 42 and 0.54 ml (3.1 mmol) of mercaptopropyltridecyldecane (43) dissolved in dichloromethane, and -78 The solution of the compound 44 was obtained in the same manner as in the synthesis of the compound 34 in Example 1. Then, 0. 37g of compound 45 was obtained by the same synthesis method of compound 35 of Example 1 using the compound 44 as described above. _ 0. 29 g (0.89 mmol) of compound 45, 0.3 g (0.89 mmol) of compound 36, and 0.44 ml (4.55 mmol) of piperidine dissolved in 12 ml of ethanol, And the synthesis method according to the synthesis method of the compound 256 of Example 1 was carried out to obtain a precipitate. Then, these precipitates were recrystallized in methylene chloride and n-octane to obtain 0.41 g (synthesis yield 7 Γ / 0 of the compound - compound 248 〇 [Example 3] Synthesis of compound 260 [Chemical reaction formula 7]

to make. 34 1309672. 0. 70 g of compound 52 by using 0.50 g (3.1 mmol) of compound 31 and 0.54 ml (3.1 mmol) of 2,7-dimercapto-5-nonane helix [4,4]-Indole-2,7-diene (51) was obtained according to the synthesis of Compound 33 in Example 1. Then, the compound 53 obtained by the method of the synthesis of the compound 35 was obtained by using 0.70 g (2.77 mmol). Using a mixed solution of 0.31 g (0.85 mmol) of compound 53, 0.28 g (0.85 mmol) of compound 36 and 0.42 ml (4.25 mmol) of φ piperidine in 10 liters of ethanol, according to Example 1. The compound 256 synthesis method obtains a precipitate which is a reaction product. These precipitates were recrystallized from ethyl acetate, and 0.31 g (yield: 53%) of the title compound Compound 260. [Example 4] Synthesis of Compound 258 [Chemical Reaction Formula 8]

The title compound 258 is synthesized according to the procedure shown in Chemical Reaction Scheme 8. 3.4 ml of gasified (tridecylmethyl indenyl) magnesium (1.0 M in diethyl ether solvent, 3.4 mmol) was mixed with 10 ml of THF and dissolved 35 i

I 1309672 4-Bromo-2-methyl-2-butene in 5 ml of THF was slowly added to the solution. The mixture was stirred at room temperature for 12 hours, and the reaction was quenched with aq. Using 0.41 g (3.16 mmol) of compound 32 and 0..49 g (3. 16 mmol) of compound 61, according to the compound 34 synthesis procedure of Example 1, 0.40 g of Compound 62 was obtained. Similarly, using 0.40 g (1.2 mmol) of compound 62, according to the synthesis method of compound 35 of Example 1, obtaining 0.226 g of compound 63 ° φ using 0.26 g (0.72 mmol) dissolved in 10 ml of ethanol a mixture of compound 63, 0.24 g (0.72 mmol) of compound 36, and 0.36 ml (3. 63 mmol) of piperidine, according to the synthesis of compound 256 of Example 1, to obtain a precipitate of the reaction product. . The precipitate thus obtained was recrystallized from n-octane and ethanol to give 0.25 g (yield: 51%) of Compound 258. [Example 5] Synthesis of Compound 250 • [Chemical Reaction Formula 9]

The subject compound 250 is according to the procedure shown in the chemical reaction formula 9 and 36 1309672 to 0, 〇·58 liter (6.4 mM) aniline '2.3 g (11.9 mM) benzodiazepine And 1.9 ml (37% aqueous solution, 25.7 mmol) of furfural dissolved in milliliters, and the mixture was refluxed for 12 hours using Dean Stark. Then cold to room temperature, 10 ml of toluene was added to ' and the mixture was kept at 0 ° C for 24 hours. The compound hydrazine was obtained by filtering the thus obtained precipitate and removing toluene from residual toluene.

Thus, the obtained compound 71 and 2.1 ml (12.9 mmol) of allyl dimethyl decane (72) were dissolved in 20 ml of dichloromethane and at -78. (After nitrogen, 12,8 liters (1.0 Torr with dichlorofurfuryl alcohol as solvent, 12.9 Torr) was added slowly. After the same method as in the synthesis of Compound 12 was used to obtain 0.60 g of compound 73' Using 0. 60 g (1.7 mmol) of compound 73, according to the synthesis method of compound 35 of Example 1, 〇. 28 g of the compound-compound 74 was obtained. 〇· 30 g (〇·78 mmol) Compound 74, 0.27 g (0.78 m)

Mox) Compound 36, and 0.39 mL (3.94 mmol) of piperidine were dissolved in 10 mL of ethanol. Then, by purifying the precipitate, 0 43 g (80% of the synthetic yield) of the compound - Compound 25, which is the same as the synthesis of the compound 2, by chromatography and recrystallization, was obtained. The reaction product. [Example 6] Synthesis of Compound 234 化学 [Chemical Reaction Formula 10] 37 1309672

The title compound 234T was synthesized according to the procedure shown in Chemical Reaction Formula 10. Using 0.48 g (3.0 mmol) of compound 32 and 0.36 ml (3.0 _ mmol) of 1-decyl-1-cyclohexane (81), according to the synthesis of compound 34 of Example 1, 0.49 g of compound 82 was obtained. 0.49 g (1.8 mmol) thus obtained Compound 82 was obtained according to the compound compound of Example 1 to give 0.39 g of Compound 83. By dissolving 0. 39 g (1.3 mmol) of compound 83, 0.28 g (1.3 mmol) of compound 84, and 0.6 ml (6.5 mmol) of piperidine in 10 The precipitate was obtained in ml of ethanol and according to the synthesis of compound 256 of Example 1. Then, the obtained precipitate was recrystallized from n-octane and di- methane to give φ of 0.36 g (yield yield: 58%) of the title compound Compound 234T. The melting point (m.p.), iH-NMR, and mass spectrometry data of a portion of the compounds synthesized according to the synthesis method of the present invention are shown in Table 5 below: [Table 5] 38 Ί 309672

Compound number»» (Ό) NMR analysis (δ) mass precursor 218 148 220 178 7.53-7.51 (m,6H), 7.47-7.44 (m,3H), 7.39-7.36 (m,6H), 7.15(d, lH), 7.08(d,lH), 6.67(d,lH), 6.52(d,lH), 6.42(d,lH), 6.07(d,lH), 3.46-3.44(m,lH), 3.34-3.20 (m,3H), 3.12-3.Q9(m.lH), 1.89-1.83(m,6H), 1.75-1.65(m,4H), 1.57-li4(m,6H), 1.36(s,3H) , 1.29(s,3H), 1.21(s,2H), 1.36-1.20(m,8H), 0.92(t,3H) 820.46 222 200 224 288 226 268 228 238 7.25(d,lH), 7.18(d, lH), 7.06(s,lH), 6.56(d,lH), 6.39(d,lH), 3.29(m,2H), 3.23(m,lH), 1.87-1.84(m,6H), 1.75(m , 4H), 1.52 (m, 6H), 1.33 (s, 3H), 1.30 (s, 3H), 1.23-1.15 (m, 8H), 0.97 (m, lH), 0.90 (t, 3H), 0.91- 0.87(m,lH), 0.09(s,9H) 633.41 230 206 234 266 236 198 7.43(d,2H), 7.34(d,lH), 7.22(d,lH), 7.08(d,2H), 7.07( s,lH), 6.52(d,lH), 6.39(s,lH), 6.37(d,lH), 3.21(m,2H), 3.09(m,lH), 2.17(m,2H), 1.80-1.78 (m,6H), 1.75(s,3H), 1.51-1.48(m,6H), 1.39(s,3H), 1.34(s,3H), 1.30-1.15(m,8H), 0.88(t,3H) ), 0.24(s,9H) 709.45 240 125 246 128 7.29(d,2H), 7.26(s,lH), 7.21(s,lH), 6.58(s,lH), 6.43( s,lH), 6.40(d,lH), 3.29(m,4H), 2.19-2.01(m,6H), 1.78(m,4H), 1.56-1.54(m,8H), 1.43(s,2H) , 1.33-1.12(m,18H), 1.02-〇.92(m,2〇H) 254 268 256 200 7.29(d,lH), 7.25(d,lH), 7.16(d,lH), 6.59(d , lH), 6.43(d,lH), 6.40(d,lH),3_31(t,4H), 1.87(m,8H), 1.76(t,2H), 1.53(m,6H), 1.32(s, 6H), 1.21(s,4H), 1.26-1.20(m,8H), 0.92(t,3H), 0.03(s,9H), -0.04(s,9H) 719.47 258 204 7.27(d,lH), 7.24(s,2H), 6.58(d,lH), 6.43(d,lH), 6.426(d,lH), 4.43(m,lH), 3.35(t,2H), 3.09(m,lH), 1.87 (m,6H), 1.78(m,3H), 1.56(m,6H), 1.35(s,3H), 1.31(s,3H), 1.24(s,3H), 1.21(s,3H), 0.913( t,3H), 0.94-0.89(m,2H), 0.62(m,lH),0.41(m,2H), 0.011(s,9H) 675.46 39 1309672 Compound Codification*» (X:) NMR Analytical Quality糌260 238 7.27(s,lH), 7.22(d,lH), 7.23(s,1H), 6.57(s,lH), 6.41(d,lH), 5.47(d,lH), 3.37-3.29( m^H), 2.08(m,lH)I 1.87-1.84(m,6H), 1.79-1.62(m,5H), 1.54(m,6H), 1.53-1.26(m,4H), 1.35(s, 6H), 1.27(s,3H), 1.26-1.22(m,8H), 1.17-1.03(m,3H), 0.90(t,3H), 0.66-0.61(m.lH)_L_ 683.43 270 296 &quot;300 ~ s 306 308 ~3Ϊ0~ ~3Ϊ2&quot; ~ 314~230~300~~Ϊ80~ Ί98~ &quot;Ϊ20~ ~2^~ ~208~ ~204~ ~2Ϊ0~ ~218~ [Example 7] Manufacture and evaluation of organic electroluminescent elements (method 1) The organic electroluminescent device shown in Fig. 1 was obtained by synthesizing a red electroluminescent compound as an electroluminescent dopant of the present invention. The transparent electrode ΙΤ0 thin layer (2) (15 Ω / Ιϋ) made of organic electroluminescence glass (1) (Samsung-Corning) is sequentially subjected to ultrasonic cleaning using triethylene glycol 'acetone, ethanol, and distilled water, and then Place isopropyl alcohol, store, and use. The ΙΤ0 substrate is placed on the substrate holder of the vacuum evaporation apparatus, and the Ν 'Ν'-bis(cc~naphthyl)-oxime, Ν'-diphenyl-4,4,-amine represented by the formula 106 (ΝΡΒ) Put in the steaming tube (ceil) in the vacuum distillation equipment, and then evacuate until the vacuum in the processing chamber in the equipment reaches 1〇_6 torr. A 40-nm thick hole transfer layer (3) was deposited on the ΙΤ0 substrate by applying a current to the vapor deposition tube and vapor-depositing NPB'. Next, ginseng (8-hydroxyquinoline)-aluminum (Alq) represented by Chemical Formula 107 is placed at 1309672 into another vapor deposition tube of the above vacuum evaporation apparatus, and the electroluminescent dopant synthesized in Example 丨6 is used. Put other (10) tubes. New, through the steaming and doping of the above two materials at different speeds, depositing a thick red electroluminescent layer (4) on the above-mentioned hole transport layer, wherein the doping concentration of the electroluminescent dopant accounts for the Alq concentration 1-1% of the moles. Thereafter, a 40-nm thick Alq was deposited as an electron carrying layer (5) on the electroluminescent layer in the same deposition method as NPB. Further, a 2-nm thick lithium quinoline represented by the formula 110 is redeposited as an electron injection layer (6). As described above, the organic electroluminescent element shown in Fig. 1 is obtained by depositing an A1 cathode (magic to a thickness of 150 nm) after forming the organic layer (7) by another vacuum evaporation apparatus. [Example 8] Manufacture and evaluation of electroluminescent elements (Method 2) Organic electroluminescent elements are prepared by synthesizing a red electroluminescent compound as an electroluminescent dopant of the present invention. (Samsung_c〇rning) The transparent electrode TM thin layer (2) (addition / mouth) is sequentially ultrasonically cleaned with triethylene ethoxide 'acetone 'ethanol' and steamed, and then placed in isopropyl alcohol, and stored. And use. The ruthenium substrate is placed on a substrate holder of a vacuum evaporation apparatus, and Ν, Ν, -bis(α~naphthyl)_Ν, Ν, _diphenyl _4, 4, _ An amine (ΝΡΒ) is placed in a steaming tube in a vacuum evaporation apparatus, and then evacuated until the vacuum in the processing chamber in the apparatus reaches 10-6 Torr. The current is applied to the vapor deposition tube and the deposited NPB' deposit The 40-nm thick hole transfer layer (3) is on the ITO-based 1309672 board. The receiver is shown in Equation 1〇7. Aiq and the red olefin (rUbrene) shown in the chemical formula 108 are placed in the above vacuum distillation (four) and the other two steamed minerals i &amp; the electroluminescence exchange synthesized in the real and the examples 1, 6 are placed in other steaming &amp; woven, depositing a -2G-nm thick electroluminescent layer (4) on the above-mentioned electro-transport layer, wherein the doping of red fluorene is 50-150 mol%, and the electroluminescence is replaced by The concentration accounts for 10 mol% of the Aiq concentration. Thereafter, a 40 nm thick A1q is deposited as an electron transport layer (5) on the electroluminescent layer by the same deposition method as NPB. Further, a chemical formula 110 is deposited. The 2-nm thick is shown as the electron injection layer (6). The organic electroluminescent element shown in Fig. 1 as described above is deposited by an additional vacuum evaporation apparatus after forming the organic layer (7). (8) to a thickness of 150. [Example 9] Production and evaluation of organic electroluminescence device (Method 3) Organic electroluminescence device was synthesized by the present invention as a red photoelectroluminescent compound as an electroluminescence # dopant Prepared by transparent ITO thin film made of organic electroluminescence glass (1) (Samsung-Corning) (2) (15 Ω / [ϋ) is used in order to use ultrasonic cleaning, triglyceride, ethanol, and steamed water for ultrasonic cleaning, then add isopropyl alcohol, storage, and use. Put on the substrate holder of the vacuum evaporation apparatus, and put the Ν 'Ν'-bis(α-naphthyl)-Ν 'Ν'-diphenyl-4,4'-diamine (ΝΡΒ) shown in Chemical Formula 106 into The vapor-deposited tube in the vacuum evaporation apparatus is then evacuated until the degree of vacuum in the chamber of the 42 1309672 is reached. A thick hole transfer layer (3) is deposited on the substrate by applying a current to the smelting g and ':, plating NPB'. Next, the other two steamed tubes prepared by the above-mentioned vacuum steaming (four) shown in Mq of Chemical Formula 107 and the red fluorescene shown by Chemical Formula 1〇8, and Example 1 are used. The electricity generated by the electricity is released into other vapor-deposited tubes. However: after the steaming and doping of the above three materials at different speeds, the electroluminescence layer (4) with a thickness of -2Gnm is transmitted in the above hole, wherein the concentration of the red sage is 50-150 mo The ear%, and the doping concentration of the electroluminescent dopant accounts for 1-1% of the Alq concentration. Thereafter, a 10-nm thick 2'9-methyl-4'7-diphenyl-phenanthroline (BCP) represented by Chemical Formula 109 was deposited as a hole transport layer on the deposited layer. Further, a 40-nm thick Alq was deposited as an electron transporting layer (5) on the above electroluminescent layer in the same deposition method as NPB. A 2-nm thick quinolate (Liq) as shown in Chemical Formula 110 is deposited as an electron injection layer (6). # As described above, the organic electroluminescent element shown in Fig. 1 is obtained by depositing a tantalum 1 cathode (8) to a thickness 150 after forming an organic layer (7) by another vacuum evaporation apparatus. [Chemical Formula 106]

43 1309672 [Chemical Formula 107]

[Chemical Formula 109]

[Chemical Formula 110]

The results of the analysis of the luminescent properties of the red electroluminescent compound of the present invention are shown in Table 6. The material of the present invention shows a significant improvement in its luminescent properties compared to DCJTB, which is known to have the best luminescent properties. In the case of the maximum illuminating wavelength, the material of the invention shows a substantially similar wavelength band, and the luminescence peaks of many materials appear in the longer wavelength band than DCJTB. It was also confirmed that there was no peak of the main illuminant Alq (as shown by the chemical formula ι 7). The group of compounds having a methylidene substituent indicates that the current mobility of the element is increased, thereby confirming that the luminance is also increased. Moreover, the group of compounds containing the ring of the ring shows an improved luminance due to the steric barrier effect which almost maintains the wavelength of the light. The group of compounds in the electron acceptor moiety that was indulged by a diketone substituent (rather than a dicyano group) showed a significant improvement in color coordinates, but the luminance did not decrease. [Table 6] The evaluation results of the organic electroluminescence device of the present invention were as follows.

45 1309672

Compound|luminescence (nm) luminance at 12,000 cd/m2 current density luminescence color coordinate structure 218 610 1.34 5.7, 70, (0.611, 0.384) Alq: Red218 2% 400/200/400 220 596 5.32 11.8, 627, (0.533, 0.449) Alq: Red220 1% 400/200/400 612 3.82 10.7, 352, (0.606, 0.392) Alq70%+Rub 30%: Red220 1% 400/200/40 222 604 3.21 18.1, 587, (0.554, 0.431) Alq: Red222 1% 400/200/400 228 612 1.71 38.8, 561, (0.582, 0.404) Alq: Red228 1% 400/200/400 230 608 4.62 14.3, 626, (0.568, 0.420) Alq :Red230 1% 400/200/400 618 4.0 252.5, 7218, (0.633, 0.364) Alq+Rub 40%: Red230 2% 600/200/300/400 234 604 5.5 15.4, 741, (0.57, 0.421) Alq: Red234 1% 400/200/400 602 4.7 269, 11540, (0.555, 0.42) Alq: Red234 0.6% 400/200/400 618 1.8 208, 3525, (0.608, 0.381) Alq: Red234 2% 400/200/400 612 3.65 342, 7324, (0.59, 0.401) Alq+Rub 30%: Red234 0.6% 400/200/400 626 1.33 139.6, 1825, (0.611, 0.382) Alq: Red234 3% 500/300/500 236 598 6.15 15.8 , 918, (0.546, 0.443) AIq: Red236 1% 400/200/400 608 4.2 18.1, 682, (0.578, 0.420) AIq70%+Rub 30%: Red236 1% 400/200/400 46 1309672 Compound electroluminescence first Uim; brightness at 12 cd/m2 12V "Flow density first Si color seat-like structure 234T 626 4.47 266.5, 8765, (0.631, 0.365) AIq+Rub50%: Red234T 2% 100/400/300/500 238 612 2.28 237.4, 4849, (0582, 0.408) Alq: Red238 2% 600/200/300/ 400 614 2.26 161.5, 3577, (0.593, .0.401) AIq: Red238 2%/BCP 600/200/300/100/300 618 4.16 342.7, 8895, (0.607, 0.387) Alq+Rub 40%: Red238 2% 600 /200/300/400 250 606 2.45 352, 13510, (0.553, 0.417) Alq: Red250 0.6% 400/200/400 254 604 5.7 150,7409, (0.537, 0.446) Alq: Red254 0.6% 400/200/400 604 1.46 386.8, 5029, (0.6, 0.391) Alq: Red254 2% 400/200/400 614 3.3 465.7, 7170, (0.589, 0.404) Alq+Rub 30%: Red254 0.6% 400/200/400 256 612 2.15 170 , 3474, (0.599, 0.388) Alq: Red256 2% 400/200/400 620 4.76 272, 8716, (0.623, 0.372) Alq+Rub 30%: Red256 2% 500/300/500 260 604 5.5 329, 14910, (0.548, 0.424) AIq: Red260 0.6% 400/200/400 612 1.90 302.4, 5476, (0.585 , 0.402) Alq: Red260 2% 400/200/400 620 3.9 313, 7520, (0.61, 0.385) Alq+Rub 40%: Red260 2% 600/200/300/400 334 636 4.7 317, 11400, (0.653, 0.340) Alq+Rubrene 40%: Red 334 2% 600/200/300/400 354 638 3.6 330, 10560, (0.656, 0.335) Alq+Rubrene 40%: Red 354 2% 600/200/300/400 335 642 3.3 297, 9520, (0.660, 0.328) Alq+Rubrene 40%: Red 335 2% 600/200/300/400 [industrial use] As described above, compared to the traditional dicyano-jumololidine (DCJ)-based Fluorescent material, the red electroluminescent compound of the invention has very superior luminescent properties, and is also very suitable for the manufacture of pure red organic electroluminescent panel due to its superior color purity, and is very efficient in manufacturing high efficiency. Organic electroluminescent panel. Although the present invention has been described with reference to the preferred embodiments, it is understood that the invention is not limited by the detailed description. 47 修修 Poverty Relief. Patent Application Chinese Manual Replacement Page '(March 98) Replacement and modification styles have been suggested in the previous description, and alternatives and modifications will be made to those skilled in the art. Think about it. In particular, the system and method of the present invention, all of which are substantially identical to the components of the present invention and which achieve substantially the same results as the present invention, do not depart from the spirit of the invention. Therefore, all such alternatives and modifications are intended to be within the scope of the invention as defined by the appended claims and their equivalents. BRIEF DESCRIPTION OF THE DRAWINGS The structure and method of the present invention will be described in detail below. The present invention is not intended to define the present invention. The invention is defined by the scope of the patent application. The embodiments, features, aspects, and advantages of the present invention will be fully understood from the following description of the appended claims. 1 is a schematic view showing the structure of an organic electroluminescence device obtained in Example 7; FIG. 2 is a diagram showing the electroluminescence spectrum of DCJTB shown in Chemical Formula b; and FIG. 3 is a view showing the synthesis of Example 3. Electroluminescence spectrum of Compound 234T; Figure 4 shows the current density-voltage characteristics of Compound 234T disclosed in Example 9; Figure 5 shows the luminosity-voltage characteristics of Compound 234T disclosed in Example 9; The luminance-luminance characteristic of the compound 234T disclosed in Example 6 is shown; and the seventh panel shows the color holder 48 1309672 of the compound 234T disclosed in Example 7. The luminescence-luminescence characteristic. [Main component symbol description] Organic electroluminescence glass (1) Transparent electrode ΙΤ0 thin layer (2) Hole transfer layer (3) Thick electroluminescent layer (4) Electron transport layer (5) Electron injection layer (6) • Organic layer (7) A1 cathode (8)

49

Claims (1)

Ii ii y\ jL· Slogan Patent Application Macro Scope #换本(March 98) X. Patent application scope: 1. An organic electroluminescent compound having the structure shown by the following chemical formula i: [Chemical Formula 1] Wherein R1 and R2 are independently of each other, and each of ri and r2 may be hydrogen, a chain length of Ci-C1G branched or linear alkyl, aryl, adamantyl, 4-pentylbicyclo[2,2, 2] octyl or R&quot;R12Rl3Si-, or Ri and r2 can be obtained by _ch2ch2ch2ch2ch2- Connecting to form a helical ring; R3 and R4 are independent of each other, and each of the enthalpy and R4 may be hydrogen or a bond having a chain length of Cl _ Cio or a straight bond; R5 and R6 are independent of each other, and each of the R5 and R6 may be hydrogen or a bond having a chain length of Cl _ Cio or a direct bond; the R 1 and R 5 or R 4 and R 6 may be represented by _CH 2 CH 2 CHr, - CH2CH2CH2CH2- or CH3 is bonded to form a melting ring; the alkyl, aryl and aralkyl groups of R1 'R2, R3, R4, R5, and R6 may be additionally substituted by more than one RnR12R13Si-; R7 is chain length C - a branched or straight chain alkyl group of C1G, a cycloalkyl group of cs-c7, an aryl group, an adamantyl group or a 4-pentylbicyclo[2,2,2]octyl group, the cycloalkyl group of the R7 The aryl group may be additionally substituted by more than one chain or q-C1() branched or linear alkyl group of 50 乜 09,672; R8 and R9 are both -CN or may be through a _ ring; The connection forms a 1,3-block full R, R 2 'and R13 are the same or different from each other, and each of the R&quot;, r12, and r13 has a bond length c--Cig branch or a direct bond or a aryl group Base; condition is r1, R2, And R is not a bond or a bond length of C]-Ciq or a direct bond. 2'. The organic electroluminescent compound according to claim 1, which has the following chemical formula 2: [Chemical Formula 2] R6 R4 Wherein η is an integer 〇 - 1〇; R2 ′ R3 ′ R4, R5, R6, R7, R8 ′ R9, R11, Rl2, and Rl3 are as defined in claim 1. 3. The organic electroluminescent compound according to 5, wherein: the R is hydrogen 'methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl-pentane Base, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl 'n-decyl, phenyl, naphthyl, adamantyl, 4-pentylbicyclo[2,2,2] 51 1309672 octyl 'tridecyl fluorenyl, triethylmethyl decyl, tri (n-propyl) decyl, tris(isopropyl)carboxyalkyl, tri(n-butyl)carboxyalkyl, three ( Isobutyl)carbenyl, tris(tert-butyl)carboxyalkyl, tris(n-pentyl)decyl, tris(isopentyl)carboxyalkyl, tert-butyldimethylformamidinyl, or tri Phenylcarboxyalkyl; R3 'R4, R5 and R6 are independently of each other hydrogen, methyl, ethyl, n-propyl, iso-amp; propyl, n-butyl, isobutyl, tert-butyl, n-pentyl , isopentyl, n-hexyl, n-heptyl 'n-octyl, 2-ethylhexyl, or n-decyl; and the alkyl of R 2 ' R 3 , R 4 , R 5 and R 6 may additionally be trimethyl decyl decane Base, triethyl decyl, Tris(n-propyl)formamidinyl, tris(isopropyl)methylhydrazine-tris(n-butyl) fluorenyl, tris(isobutyl)carbenyl, tris(tert-butyl)anthracene Alkyl, tris(n-pentyl)decyl, tris(isopentyl)carboxyalkyl, tert-butyldimethylcarbonyl, or triphenylsulfonyl. I. The organic electroluminescent compound according to claim 1, which has the following chemical formula 3 or 4: [Chemical Formula 3] 52 1309672 [Chemical Formula 4] Wherein the substituents R2, R3, R4, R6, and R7 are as defined in claim 1 The A can be independently of each other as -CH2-, -CH2CH2-, or ch3. 5. The organic electroluminescent compound according to claim 4, which has the following chemical formula 5 or 6: [Chemical Formula 5] R6 R4 [Chemical Formula 6] 53 1309672 Wherein R2, R3, R4, R6, and R7 are as defined in claim 1. 6. The organic electroluminescent compound according to claim 1, which comprises a helical ring of Chemical Formula 7 or 8: [Chemical Formula 7] [Chemical Formula 8] Wherein R3, R4, R5, R6, R7, R8, and R9 are as defined in claim 1. 54 1309672 7. The ruthenium electroluminescent compound of claim 1 having the following chemical formula 9·· [Chemical Formula 9] And an organic electroluminescent compound according to claim 1, wherein the R7 is independent of each other and is selected from a methyl group. Ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl 'n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n- , cyclopentyl, 2-methylcyclopentyl, 3-fluorenylcyclohexyl, cycloheptyl, Φ phenyl 'tolyl, naphthyl 'adamantyl' or 4-pentylbicyclop, 2, 2] Octyl 9, an organic electroluminescent compound according to claim 1, which is selected from the group consisting of the following compounds: 55 1309672 (Ph) 3Si 56 1309672 57 1309672 NC Si(CH3)3 t-Bu NC CN Π-〇5Η ί NC NC Si(CH3)3 t-Bu NC n-CsH-n Si(CH3)3 58 1309672 59 1309672 60 1309672 61 1309672 62 1309672 63 1309672 A method for producing an organic electroluminescent compound according to Chemical Formula 1 of Claim 1, which comprises: a) synthesis of a tetrahydroquinoline derivative (C), wherein 64 Ϊ 309672 is derived from tetrachloro The presence of tin in the presence of tin, the aniline derivative (a) and the hydrocarbonene street organism (8) with a substituent of be(10) triazoly丨methane (Friedd_Crafts); b) The synthesis of Julius (F), a tetrahydroquinone derivative (4) prepared from the tetrahydrofuran derivative (C) by a tetrakilylidene derivative (C) And in the presence of four vaporized tin, the tetrahydroquinoline derivative (D) having the arachidyl diazolyl methane substituent and another hydrocarbon riding organism (E) are carried out by Frederick Kraft a specific reaction; c) synthesis of the Julilotidine base derivative (6) in the presence of phosphorus oxyhydroxide (p〇CI3) from the quinoline derivative (F); and d) as claimed in claim 1 The synthesis of 电 械 械 电 其 其 其 其 合成 合成 合成 合成 合成 合成 合成 合成 合成 合成 合成 合成 合成 合成 合成 合成 合成 合成 合成 合成 合成 合成 合成 合成 合成pyran) derivative (H) for the reaction. [Chemical Formula 1] [Compound A] 65 1309672 [Compound B] [Compound C] [Compound D] [Compound E] Wide only 6R person 4 [Compound G] [Compound H] Re 丫 R9 The R1, R2, R3, R4, R5, R6, and R7 are as defined in claim 1. A method for producing a Julilotyl derivative (J), which comprises the step of preparing a Julilotyl derivative (J) by using di(benzotriazolylmethyl)phenylamine (di(benzotriazolylmethyl)phenylamine) (I) reacting with the hydrocarbon olefin derivative (B): 66 1309672 [Compound J] [Compound B] [Compound I] R2 R1 Bt = benzotriazole The R1, R2, and R5 are as defined in claim 1. 12. An organic electroluminescent device comprising an electrode layer; an organic electroluminescent layer; and a cathode; wherein the organic electroluminescent layer comprises the organic device according to any one of claims 1 to 9. The luminescent compound acts as a red electroluminescent material. 67