TW201144281A - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

Abstract

Provided are a novel organic electroluminescent compound and an organic electroluminescent device using the same. Since the organic electroluminescent compound exhibits good luminous efficiency and excellent life property, it may be used to manufacture OLEDs having very superior operation life.

Description

[Technical Field] The present invention relates to a novel organic electroluminescent (EL) compound and an organic electric field illuminating device using the same. More specifically, the organic electroluminescent compound is represented by Chemical Formula 1: [Chemical Formula 1]

N0 - In an display device, an electric field illuminating (EL) device has the following advantages as a self-emissive display device: it provides a wide viewing angle, excellent contrast, and fast reaction efficiency. Eastman Kodak pioneered the development of an organic EL device in 1987, using a low molecular weight aromatic diamine and aluminum complex as a substance used to form an electroluminescent layer [Gaga G. ZeU. 51,913, 1987]. The EL device is a type in which electrons and holes are paired with each other when charge is applied to the organic film (the film is opened/formed to the electron-injecting electrode as the cathode and the hole as the anode). And the extinction

Si set: = transparent: and _ ^ wide compared with the plasma display panel or inorganic EL display, =: EL device can be at a lower voltage (not more than 1 () volts) and relatively low dry Electricity is reduced but the color purity is different. Illumination by organic electric field (el 95122 3 201144281 (green, blue and red (in some cases, it is sometimes referred to as the lower-generation full-color display performance of mosquitoes, including luminous efficiency, operating life, etc.) Field sugar material. For the electric field luminescent material, the high electric field luminescence quantum yield, the high electron and film ability, and the resistance to decomposition in the process of product formation, and the formation of a uniform sentence-like, 胄EL device Usually has an anode/hole injection layer L / hole transport layer (HTL) / luminescent material layer (10) L) / electron transport layer / TL) / electron injection layer (EIL) / cathode configuration. emit blue, green or The organic light field illuminating device of color light can be produced according to how to form a luminescent material layer. In terms of function, the electric field luminescent material can be divided into a host material and a dopant material. Generally, it is well known. An electric field luminescent layer prepared by incorporating a dopant into a host has excellent EL characteristics. Recently, development of an organic EL device with high efficiency and long operating life has become an urgent task, especially when considering medium to large size OLEDs. surface When the grade of anal performance required for the board is required, there is an urgent need to develop materials that far exceed the traditional electroluminescent materials. Meanwhile, for the conventional blue materials, Idemitsu-Kosan developed two After styryl-biphenyl (DPVBi) (compound a), more materials were developed and commercialized. In addition to the blue material system produced by Idemitsu, Kodak's dinaphthyl ruthenium (DNA) (compound 4 95122) 201144281 b), tetra (t-butyl) flower (compound C) systems or other similar substances are also known. However, these materials should still be extensively researched and developed. Currently known as the highest efficiency The distryl compound system has a power efficiency of 6 lumens per watt and an effective device life of over 30,000 hours. However, when the system is applied to a full color display, its use due to reduced color purity with operating time There are only a few thousand hours left in life. If the electric field emission wavelength is shifted to a longer wavelength direction, it is advantageous in terms of luminous efficiency in terms of blue electric field emission. Unsatisfactory blue purity makes the material difficult to apply to high-quality displays. In addition, research and development of such materials is imminent due to problems such as color purity, efficiency and thermal stability.

Compound b Therefore, the conventional material does not form a film of a host and a dopant, but forms a single layer. Furthermore, in view of color purity and efficiency, commercialization is also difficult. The lack of reliable data for long life is also a problem. SUMMARY OF THE INVENTION Accordingly, it is an object of the present invention to provide an organic electric field illuminating compound 5 95122 201144281 which has better luminous efficiency and device operating life than conventional materials, and has an appropriate color coordinate The excellent skeleton to solve the above problem °. Another object of the present invention is to provide an organic electric field light-emitting device using the organic electroluminescent compound as an electric field luminescent material. Technical Solution In one general aspect, the present invention provides an organic electroluminescent compound represented by the chemical formula and an organic electric field light-emitting device using the same. Since the organic electroluminescent compound of the present invention has excellent luminous efficiency and excellent life characteristics, it can be used for producing an OLED having a very excellent operating life, [Chemical Formula 1].

An and An are independently represented by a (10)-'-extension moiety with or without a -C3〇), or with or without a substituent, and the IM to independently represent hydrogen, I, halogen, (C1-C30)alkyl having a substituent, having a substitution of ♦, not /, having a substituent without a substituent (C6-C30), with or without a substituent (C3- C30) Heteroaryl, substituted (C3-C30) cycloalkyl, cyano, nitro human up, -BR13R214, -PR15R16, __p(=〇)Ri7Ri8, Ri9R2()R2iSi-, heart γ - (C6_C3〇) aryl (n_C3〇)alkyl, or having no substituent, 2 having: 95122 6 201144281 (with (C2 rhyme)), or with or without a substituent The silk production 'or RdR8 may each form an alicyclic ring, or a single ring or more via a (10) wire or a (10) (10) stretching double bond to the adjacent substituted wire, with or without a slightly substituted, unsubstituted or unsubstituted The aromatic ring of the ring and the (4) ring (tetra) atom of the monocyclic or polycyclic ring may be substituted by nitrogen. Ring A and ring b are independently 5 A to 7 membered heterocyclic amine groups, and the -, cyclic amino group Can be fused to one or more aromatic rings, And further comprising one or more heteroatoms selected from the group consisting of NR., 〇, s, and SiRwR25; R11 to R25 independently represent (Ci_c3〇)alkyl with or without a substituent, with or without a substituent a (C6_C30) aryl group, or a (C3-C30) heteroaryl group with or without a substituent, or Ru to R25 may each be substituted or unsubstituted via a fused ring (C3- C30) a stretching, a radical or a (C3-C30) group is bonded to an adjacent substituent to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring; γ represents S or hydrazine; and the heteroaryl group may contain One or more heteroatoms selected from the group consisting of B, N, hydrazine, S, P (=0), Sl and p. [Embodiment] In this context, "hospital", "alkoxy" and decyl-containing alkyl" Some of the other substituents include both straight-chain and branched-chain groups. Here, "the naphthenic series contains hydrocarbons, such as adamantyl or anthracene with or without a substituent, with or without a substituent (C7) -C30) Polycyclic of a bicycloalkyl group, and a single ring. 7 95122 201144281 As used herein, "aryl" means to remove a hydrogen from an aromatic hydrocarbon. The organic group obtained after the sub-, and may contain 4 to 7 members, particularly a 5- or 6-membered monocyclic or fused ring, including a plurality of aryl groups bonded by one or more single bonds. Specific examples include, but are not limited to, phenyl, naphthyl, biphenyl, anthracenyl, fluorenyl, fluorenyl, phenanthryl, triphenylenyl, fluorenyl, fluorenyl, fluorenyl, condensed Tetraphenyl (naphchacenyl), propylenediene _ 〇 〇 luoranthenyl) and the like. The naphthyl group includes 1_caiji and 2-caiji. The thiol group includes 1-onion, 2-indolyl and 9-fluorenyl. And the fluorenyl group includes a diterpenoid, a 2-yl group, a 3-fluorenyl group, a 4-fluorenyl group, and a 9-diyl group. Herein, "heteroaryl" means one to four hetero atoms selected from the group consisting of B, N, 0, S, P (=0), Si and P as an aromatic ring skeleton atom, and other remaining aromatic rings. The skeleton atom is an aryl group of carbon. The heteroaryl group may be a 5- or 6-membered monocyclic heteroaryl group or a polycyclic heteroaryl group condensed with a benzene ring, and may be partially saturated. Further, the heteroaryl group contains a plurality of heteroaryl groups bonded by one or more single bonds. The heteroaryl group includes a divalent heteroaryl group in which a hetero atom on the ring can be formed by oxidation or quaternization, such as an N-oxide and a quaternary salt. Specific examples thereof include, but are not limited to, a monocyclic heteroaryl group such as a furyl group, a thienyl group, a pyrrolyl group, a P-mercapto group, a d ratio β-sitting group, a β-sodium-based group, a β-sei- syl group, and an isoindole. Salivation, isoindole, sputum, sputum, etc., β-sodium, indole, tri-mentyl, tetra-mentyl, succinyl, tetras-succinyl, occluded, π-bite, 0-mercapto , sulfhydryl, taphthyl, etc.; polycyclic heteroaryl, such as benzofuranyl, benzothienyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzene Isoxazolyl, benzoxazolyl, isodecyl, decyl, oxazolyl, benzothiazepine 8 95122 201144281 oxazolyl, quinalhenyl, isoquinolinyl, indolinyl, quinazoline Lysyl, quinacridine, ° cardo sit group, which bite group and benzodioxolyl, etc. 'phase N-oxide (eg pyridyl N-oxide and quinolinyl N-oxidation) And its quaternary salt. In the present invention, "(Cl-C30) alkyl, tri(C1-C30)alkylsilyl, di(C1-C30)alkyl (C6-C30) aryl fluorenyl, (C6-C30) aryl The alkyl portion of the (C1-C30)alkyl, (C1-C30)alkoxy, (C1-C30)sulfanyl group j or the like may comprise from 1 to 20 carbon atoms, more specifically from 1 to 10 carbon atoms. "(C6-C30) aryl, bis(n-C30)alkyl (C6-C30) aryl fluorenyl, tris(C6-C30) aryl fluorenyl, (C6-C30) aryl (C1 -C30) The aryl moiety of the alkyl, (C6-C30) aryloxy, (C6-C30) arylthio" or the like may comprise from 6 to 20 carbon atoms, more specifically from 6 to 12 stones. Anti-atomic. The heteroaryl portion of "(C3-C30)heteroaryl" may contain from 4 to 20 carbon atoms, more specifically from 4 to 12 carbon atoms. The cycloalkyl group in r(C3-C30)cycloalkyl" may contain 3 to 20 carbon atoms, more specifically 3 to 7 carbon atoms. The base or block group in the "(C2-C3G)alkenyl group or the block group may contain 2 to 20 carbon atoms, more specifically 2 to 1 carbon atom. The term "substituted or substituted" in the context of "substituted or unsmoothed (or with or without) substituents" as used herein means that the network is replaced by an unsubstituted substituent. Further, the substitution by the substituents UR6 and R11 to R25 may be carried out by substituting one or more substituents selected from the group consisting of (CK3〇) leukoxyl groups with or without a dentate substituent. (C6-C30)aryl, (C3-C30)heteroaryl with or without (C6_C3〇)aryl substituent, 5- to 7-membered heterocycloalkyl, with one or more 95122 9 201144281 aromatic Ring-fused 5- to 7-membered heterocycloalkyl, (C3-C30)cycloalkyl, (C6-C30)cycloalkyl fused to one or more aromatic rings, RaRbRcSi-, (C2-C30) Alkenyl, (C2-C30)alkynyl, cyano, oxazolyl, -NRdRe, -BRfRg, -PRhRi, -P(=0)RjRk, (C6-C30)aryl(C1-C30)alkyl, (C1-C30)alkyl (C6-C30) aryl, fT-, RmC(=0)-, RmC(=0)0-, carboxyl, nitro and hydroxy; or adjacent substituents may be bonded to the phase O-substituents to form a ring; Ra to R1 independently represent (C1-C30)alkyl, (C6-C30) aryl, or (C3-C30)heteroaryl; T represents S or 0; and R1" (C1-C30) alkyl, (C1-C30) alkoxy, (C6-C30) aryl, or (C6-C30) aryloxy. The ring A and the ring B are independently selected from the following structures:

Wherein Z represents a chemical bond, -(CR4lR42)m-, -(R41)C=C(R42)-, -N(R43)-, _S---0-, -Si(R44)(R45)-- -Ρ(R46)-'-P(=〇)(R47)->-C(=〇)- or -B(R48)-; feet" to R48 independently represent hydrogen, helium, halogen, with or (C1-C30)alkyl group having no substituent, (C6_C3〇)aryl group having or not having a substituent, (C3-C30)heteroaryl group having or not having a substituent, with or without a substituent (C3-C30) cycloalkyl, cyano, nitro, -NR11R12, _BR13R214, -PR15R16, -P(=〇)r17r18, Rl9R2()R2lSi_, r22Y_, with or without a substituent (C6-C30) Aryl (C1-C30) alkyl, with or without 95122 10 201144281 (C2-C30) alkenyl having a substituent, or (C2-C30) alkynyl with or without a substituent, or core to R48 Each of them is bonded to an adjacent substituent via a substituted or unsubstituted (C3-C30) stretching group or a (C3_C3〇) stretching group with or without a ring to form an alicyclic ring, or a monocyclic or polycyclic ring. Aromatic = and the pure carbon atom of the monocyclic anthracene ring formed; and in is an integer from 1 to 4. = specifically, the ring A And the ring B is independently selected from the following: not limited to this.

Ll 95122 201144281

In the formula, R!, R2, R3 and R6 each independently represent an anthracene, a halogen, a (C1-C30)alkyl group having or not having a substituent, or a (C6-C30)aryl group having or not having a substituent. The organic electroluminescent compound of the present invention is selected from the following compounds but is not limited to the following compounds. 12 95122 201144281

13 95122 201144281

The organic electroluminescent compound of the present invention can be produced by referring to the following scheme [1]. 14 95122 , > 201144281 Scheme [1]

In the formula,

The definitions of An, An, 匕 to R8, ring A and ring B are the same as defined in Chemical Formula 1. The present invention provides an organic electric field light-emitting device comprising: a first electrode; a second electrode; and one or more organic layers interposed between the first electrode and the second electrode, wherein the organic layer comprises one or more chemical formulas An organic electric field luminescent compound represented by 1. The organic electric field luminescent compound serves as a dopant material for the electroluminescent layer. Furthermore, the organic layer may comprise an electroluminescent layer, and the electroluminescent layer may further comprise one or more moieties other than one or more organic electroluminescent compounds of formula 1. The main body of the organic electric field light-emitting device to which the present invention is applied is not particularly limited. The main body of the organic electroluminescence device to which the present invention is applied may be selected from the following Chemical Formula 2 and Chemical Formula 3: 15 95122 201144281 [Chemical Formula 2] (Aru)c-Ln~(Ari2)d [Chemical Formula 3] (Ari3)e-Li2- - (Ar14)f wherein: =: 2:: a substituent having an I(10)) extended aryl group, or a thiol-substituted (C4-C60) heteroaryl group;

Ll2 represents a fluorenyl group having no or no substituent; Aru to Aru independently represents hydrogen, deuterium, halogen, (C1-C30) alkyl group with or without a substituent, with or without a substituent. (C6_C3〇) aryl, substituted or unsubstituted (C6-C30) aryl group fused to one or more (C3-C30) cycloalkyl groups with or without a substituent, with or without a substitution a 5- to 7-membered heterocycloalkyl group having a (C3-C30) heteroaryl group, with or without a substituent, and 5 to 7 members slightly overlapping with one or more aromatic rings having or without a substituent Heterocycloalkyl, (C3-C30)cycloalkyl, cyano, nitro, -NRn>iRi〇2, -BR103R1H, -PRi〇5Ri〇6, -P(=0) with or without a substituent RmRi 〇8, RmRuoUi-, RmX-, (C6-C30) aryl (C1-C30) alkyl group with or without a substituent, (C2-C30) alkenyl group with or without a substituent, with or without a (C2-C30) alkynyl group having a substituent,

Or An 1 to Αγη may each be bonded to an adjacent substituent via a substituted 16 95122 201144281 or unsubstituted (C3-C30) alkyl or (C3-C30) alkenyl group with or without a fused ring. To form an alicyclic ring, or a monocyclic or polycyclic aromatic ring; ring C and ring D independently represent a (C5-C30) alicyclic ring with or without a substituent, and a (C6-C30) aroma with or without a substituent a ring, or a (C6-C30) heteroaromatic ring with or without a substituent;

Rm to Rm independently represent a (C1-C30)alkyl group having or not having a substituent, a (C6-C30) aryl group having or not having a substituent, or a (C3-C30) heteroaryl group having or not having a substituent. X; S represents S or 0; W represents a chemical bond, -(CRl3lRl32)n-, -(Rl31)C = C(Rl32)-, -N(Rl33)-, -S-, -〇-, -Si(Rl34 )(Rl35)-, -P(Rl36)-, -P(=0) (Rl37)-, _C(=0)- or -B(Rl38)-;

Rl21 to Rl23 and Rl31 to Rl38 have the same definitions as Aril to ;4; the heterocycloalkyl or heteroaryl group may contain one or more selected from the group consisting of ruthenium, osmium, 0, S, P(=0), Si and a hetero atom of P; η is an integer from 1 to 3; and c, d, e, and f are independently represented as an integer of 0 to 4. The host compound of the formula [2] or [3] can be exemplified by a compound having the following structure, but is not limited thereto. 17 95122 201144281

18 95122 201144281

In the organic electronic device of the present invention, the organic layer comprises, in addition to the organic electroluminescent compound represented by Chemical Formula 1, a group further comprising one or more selected from the group consisting of an arylamine compound and a styrylarylamine compound. Compound. The arylamine compound or the styrylarylamine compound is exemplified in Korean Patent Application No. 10-2008-0123276, No. 10-2008-0107606, or No. 1~20〇8-〇ι18428, but not Limited to this. Furthermore, in the organic electric field light-emitting device of the present invention, in addition to the organic electric field luminescent compound represented by the chemical wind-V 1 _ ^ a 巧巧1, 95122 19 201144281 may further comprise one or more selected from the group consisting of A metal or complex compound of a group of organometallics, Group 2, transition metals of the fourth and fifth cycles, lanthanide metals, and d-transition elements. The organic layer may include an electric field luminescent layer and a charge generating layer. In addition, the organic layer may contain, in addition to the organic electroluminescent compound represented by Chemical Formula 1, a layer or a plurality of organic electroluminescent layers emitting blue, green or red light to specifically implement organic light emitting white light. Electric field illuminating device. The compound which emits blue light, green light or red light is disclosed in Korean Patent Application No. 10-2008-0123276, No. 10-2008-0107606, or No. 1 2008-0118428, but is not limited thereto. In the organic electroluminescence device of the present invention, a layer (hereinafter referred to as "surface layer") selected from a chalcogenide layer, a metal layer and a metal oxide layer may be provided on the electrode pair. On the inner surface of one or both electrodes. More specifically, a metal chalcogenide (including oxide) layer of ruthenium or aluminum may be disposed on the anode surface of the electric field luminescent medium layer, and a metal halide layer or a metal oxide layer may be disposed on the electric field luminescent medium. On the cathode surface of the layer. Thereby, operational stability can be obtained. The chalcogen compound may be, for example, SiOx (l$x^2), ΑΙΟχx$1.5), SiONO, SiA10N or the like. The metal halide may be, for example, UF, %F2, CaF2, a fluoride of a rare earth metal, or the like. The metal oxide may be, for example, Cs2〇, Li2〇, MgO, SrO, BaO, CaO or the like. In the organic electric field light-emitting device of the present invention, it is also preferable to provide a mixed region of the electron transporting compound and the reducing dopant or a mixed region of the hole transporting compound and the oxidizing dopant in the electrode pair thus manufactured. To 95122 20 201144281 Less one on the surface. In this way, since the electron transporting compound is reduced to an anion, the electrons are facilitated to be injected and transported from the mixed region to the electric field illuminating medium. In addition, since the hole transporting compound is oxidized to form a cation, the hole is facilitated to be injected and transported from the mixed region to the electric field illuminating medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds. Preferred reducing dopants include metalloids, metal-detecting compounds, soil-measuring metals, rare earth metals, and mixtures thereof. Further, an electric field emitting device for emitting white light having two or more layers of an electroluminescent layer is manufactured by using a reducing dopant layer as a charge generating layer. Advantageous Effects Since the organic electroluminescent compound of the present invention has good luminous efficiency and excellent life characteristics, it can be used to manufacture an OLED having a very excellent operational life. Mode for Invention The present invention further describes the organic electroluminescent compound of the present invention, a process for preparing the compound, and a light-emitting property of a device using the compound. However, the following specific examples are for illustrative purposes only and are not intended to limit the scope of the invention in any way. [Preparation Example] [Preparation Example 1] Preparation of Compound 3 21 95122 201144281

Preparation of compound 1-1, 9,9-diethyl-9H-indole (7.0 g (g), 32.11 mmol (mmol)) and polyoxymethylene (9.4 g (g), 32. 11 mmol) Ear (_〇1;)) dissolved at 30 ° /. HBr (50 (ml) mL), and at 6 〇. (: The mixture was stirred for 24 hours. When the reaction was completed, the reaction mixture was extracted by adding water and gas imitation. The water was removed by M g S 04 and distilled under reduced pressure, and then layered through a column (MC/ Compound 1-1 (13 g (g), 318 mmol (mm 〇 1), 99%). Preparation of compound 1-2 Compound 1 g (g), 12.24 mmol (1) It was dissolved in triethyl sulphate (8. liters (mL), 48 96 mM (1);), and 185d-Wei compound for 6 hours. When the reaction was completed, the remaining miscellaneous triethyl vinegar was removed by vacuum evaporation of α. The reaction mixture was washed with steamed water and extracted with acetic acid. The water of the organic layer was removed by MgSG4, and the money was evaporated under reduced pressure, and then the mixture was layered through a column using ethyl acetate to obtain compound #1-2 (19 g (2), 9 37 mmol (1) 76%). Preparation of compound 1-3, hydrazine, 2'3,4-tetrahydroquinoline (10 g (g), 75.0 mmoles 22 95122 201144281 (mmol)) 4 曱驴 benzene succinic acid (5.6 g (g), 37. 5 millimolar (mmol)), Pd(〇Ac)2 (〇〇2 g (g), 19 mmol (legs 1)), P(t-Bu) 3 (1.5 mL, 3.7 mmol) (50% in toluene) and Cs2C〇3 (36.7 g (g), 112.5 mmol (mm〇i)) were dissolved in toluene (75 ml (mL)) and the mixture was stirred at 11 ° C for 5 hours. . When the reaction was completed, the mixture was cooled to room temperature and the mixture was extracted with ethyl acetate/water (1:1). The water was removed by MgS〇4 and distilled under reduced pressure, and then compound 13 (4·9 g (S), 20-6 mmol (face. 1), 55%) was obtained by layering through a column. Compound 3 was prepared by dissolving compound r\ 9.56 mmol) and compound 1-3 (45 g, 19.13_〇1) in gas, tetraflurane (50 ml (mL)), and the mixture was cold. To 0 C, then Λ — - ^ + t, Ling added potassium butoxide (1.0 molar concentration (Μ) in tetrahydrofuran, 19 mM rniT,,, . ^UL)) ° when slowly increasing the temperature The mixture M was stirred and an excess of steamed water was added. Thereby, a precipitate was obtained and the precipitate was filtered off. The solid precipitate obtained by washing with 乙, Q c; v. drenched to obtain compound 3 (3.5 g of organic electric field luminescence ML-1 λ 53%). And prepared. , Compounds 1 to 29 are according to the MS/FAB data of the preparation example [1]. 1H NMR and 23 95122 201144281 Table 1 Compound 1H NMR (CDCI3t 200 MHz) MS/FAB Measured value 1 δ = 0.9(6H, m), 1.91(4H, m) , 3.05(4H, m), 4.14(4H, m), 6.55-6.6(6H, m), 6.72(2H, m), 6.95(4H, m). 7.05~7.07(4H, m), 7.54(2H , m), 7.71 (2H, m), 7.8(4H, m), 7.87(2H, m) 660.89 660.35 2 δ = 0.9(6H, m), 1.91(4H, m)t 6.52(2H, m), 6.87(2H, m), 6.95(4H, m), 7.33(2H, m), 7.5-7.62(12H, m)f 7.71(2Ht m), 7.87-7.94(6H, m) 656.86 656.32 3 δ = 0.9 (6H, m), 1·9 Bu 1.96 (8H, m>, 2·76(4Η, m), 3.06(4H,m), 6.55-6.6(6H, m), 6.72(2H, m), 6.95 (4H, m), 7.05-7.07(4Hl m), 7.54(2H, m)t 7.71(2H, m), 7.8(4H, m), 7.87(2H, m) 686.94 688.38 4 δ = 0.9(6H, m), 1.25(12H, m), 1.77(4H, m), 1.91(4Ht m), 2.79(2Ht m), 2.94(2H, m), 6.52(2H, m), 6.6(4H, m), 6.69(2H, m), 6.95(4H, m), 7.05-7.08(4H, m), 7.54(2H, m). 7.71(2Ht m), 7.8(4H, m), 7.87(2H, m} 745.05 744.44 5 δ = 0.9(6H, m), 1,91-1.96(8H, m), 2·76(4Η, m), 3.06(4Η· m), 6.55-6.6(4H, m), 6.72(2H , m), 6.95(4H, m) , 7.04-7.07(5H, m), 7.53-7.56(6H, m)( 7.64(2H, m), 7.71(2H, m), 7.78-7.8(3H, m), 7.87(2H, m), 8.07 (1 H, m), 8.49 (1 H, m) 815.09 814.43 6 δ = 0.9(6H, m), 1.91(4H, m). 3.81(4H, s)t 6.51(4H, m), 6.63(4H , m>, 6.69(4H, m), 6.95-7.01(12H, m)· 7.54(2H, m), 7.7, 7·77(6Η, m), 7.87(2H, m) 785.03 784.38 7 δ = 0.9 (6Hf m), 1.72(12H, s), 1.91(4H, m), 6.55(4H, m), 6.63(4H, m)_ 6·73(4Η,m), 6.95(4H, m), 7.02 -7.05(8H, m). 7.54(2H, m), 7.71-7.77(6H, m), 7.87(2H, m) 841.13 840.44 8 δ = 0.9(6H, m), 1.91(4H, m), 6.63 (4H, m), 6.95-6.97(8H, m), 7.16~7.21(12H, m), 7.54(2H, m). 7·71-7.77(6Η, m), '7.87(2H, m) 821 , 10 820.29 9 δ = 0·9(6Η, m), 1.91(4H,m), 6.59-6.63(8H, m), 6.77(4H,m), 6.89-6.95(12H, m)t 7.54(2H , m), 7.71-7.77(6H, m), 7.87(2H, m) 788.97 788.34 10 δ = 0.66(12H, s), 0.9(6Hf m), 1.91(4Ht m), 6.63(4H, m), 6.73(8H, m), 6.95(4H, m), 7.21(4H, m), 7.3(4H, m>, 7.54(2H, m). 7.71-7.77(6H, m), 7.87(2H, m) 873,28 872.40 24 95122 201144281 11 δ = 0.9(6Η, m), 1.91(4Η, m), 6.38( 8Η, m), 6.56(8Η, m), 6.63(8Η, m), 6.81 (2Η. m), 6.95(4Η, m), 7.2(4Η, m). 7.54(2Η, m), 7.71-7.77 (6Η, m), 7.87(2Η, m) 939.19 938.43 12 δ = 0.9(6Η, m), 1.91(4Η, m), 2.88(8Η, m), 6.58~6.63(8Η, m), 6.76(4Η , m), 6.95(4Η, m), 7.〇2-7.04(8Η, m), 7.54(2Η, m), 7·71~7·77(6Η, m), 7·87(2Η, m 813.08 812.41 13 δ = 0.9(6Η, m), 1.91(4Η, m), 6.63(4Η, m), 6.69(4Η, m), 6.87(4Η, m), 6.95(4Η, m), 7.16( 4Η, m), 7.47(4Η, m), 7.54(6Η, m), 7.71-7.77(6Η, m), 7.85-7.87(6Η, m) 909.16 908.41 14 δ = 0.9(6Η, m), 1.91( 4Η, m), 6.63(8Η, m), 6.81 (4Η, m), 6.95-7.05(12Η, m), 7.25(4Η, m), 7.54(2Η, m), 7.71-7.77(6Η, m) , 7.87(2Η, m) 809.05 808.38 15 δ = 0.9(6Η, m), 1.25(6Η, m), 1.81(2Η, m), 1,91(6Η, m), 2.79"2.8(6Ht m) , 6.55~6.6(6H, m), 6.72(2H, m). 6.95(4Hf m), 7.05-7.07(4H, m), 7.54(2H, m), 7.71(2H, m), 7.8(4H, m), 7.87(2H, m) 716.99 716.41 16 δ = 0.9(6H, m), 1.33(6H, m), 1.91(4H, m), 3.48(2H, m), 5.92(2H, m), 6.55 *6.6(6H, m), 6.72(2H, m), 6.82(2HI m), 6.95(4H, m), 7.11-7.16(4H, m), 7.54(2H, m), 7.71(2H, m), 7.8(4H, m)t 7.87(2Ht m) 712.96 712.38 17 δ = 0.9(6H, m), 1.91(4H, m), 3.73(4H, m), 5.92(2H, m), 6.55-6.6(6H, m), 6.72(2H, m), 6.82(2H, m). 6.95(4H, m) f 7.11~7.16(4H, m)( 7.54(2HI m), 7.71(2H, m), 7.8(4H, m)t 7.87(2H, m) 684.91 684.35 18 δ = 0.9(6H, m), 1.91( 4H, m)f 2.34(6H, s). 3.05(4H, m), 4.14(4H, m), 6.43(2H, m), 6.6(4H, m), 6.83(2Hf m), 6.94-6.95( 6H, m). 7.54(2H, m), 7.71(2HI m), 7.8(4H? m), 7.87(2H, m) 688.94 688.38 19 δ = 0·9(6Η, m), 1·25(6Η , m), 1.81(6H.m)·1·91(4Η, m), 2.12(6H, s), 2.34(6H, s), 2_79-2_8(4H, m), 6·6(4Η, m ), 6.7—6·75(4Η, m), 6.95(4Ht m), 7.54(2H, m), 7.71(2H, m), 7.8(4H, m), 7.87(2H, m) 773.10 772.48 25 95122 201144281 20 δ = 0.9(6Η, m), 1.91(4Η, m), 6.52(2Η, m), 6.95(4Η, m), 7.41 (2Η, m), 7.5-7.62(20Η, m), 7.71- 7.77(4Η, m), 7.87(2Η, m), 8(2Η, m), 8.18(2Η, m) 809.05 808.38 21 δ = 3.05(4Η, m), 4.14(4Η, m), 6.55-6.6( 6Η, m)( 6.72(2Ht m), 6.95(4H, m), 7.05-7.07(4H? m), 7.16-7.19(4H, m ), 7.35(2H, m), 7.54{2H, m)f 7.71-7.8(8H, m), 7.87(2H, m) 754.96 754.33 22 δ = 0.9(6H, m), 1.91-1.96(8H, m ), 2.76(4H, m), 3.06(4H, m), 6.55~6.6(4H, m). 6.66-6.72(4H, m), 6.95(4H, m), 7.05~7.07(4H, m), 7.54~7.57(6H, m), 7.64(2H, m), 7.71 (2H, m), 7.8(2H, m), 7.87(2H, m) 765.04 764.41 23 δ = 1.96(4H, m), 2.76( 4H, m), 3.06(4H, m), 6.55-6.6(6H, m), 6.72(2H, m), 6.95(4H, m), 7.05-7.11(8H, m), 7.26(2H, m) , 7.33(4H, m), 7.54(2H, m), 7.71(2H, m), 7.8(4H, m), 7.87(2H, m) 785.03 784.38 24 δ = 0.9(6H, m), 1.91~1.96 (8H, m), 2.76(4H, m), 3.06(4H, m), 6.55(2H, m), 6.72(2H, m), 6.96(2H, m), 7.05~7.07(4H, m), 7.2(2H, m), 7.42~7.45(4H, m), 7.56-7.59(4H, m), 7.69(2H, m), 7.82(2H, m) 690.92 690.37 25 δ = 0.9(6H, m), 1.91-1.96(8H, m), 2.76(4H, m), 3.06(4H, m), 6.55-6.6(6H, m), 6.72(2H, m), 6.95(4H, m), 7.05-7.07 ( 4H, m), 7.51-7.6(3H, m), 7.77~7.8(5H, m), 7.94(1 H, m), 8.09(1 H, m), 8.22(1 H, s), 8.52(1 H, m) 739.00 738.40 26 δ = 0.9(6H, m), 1·91Η.96(8Η, m), 2.76(4H,m), 3.06(4H, m), 6.55-6.6( 6H, m), 6.72(2H, m), 6.95(4H, m), 7.05-7.07(4H, m), 7.5W, 54(4H, m), 7.8(4H, m), 7.94(2H, m ), 8_22(2H, s), 8.52(2H, m) 789.06 788.41 27 δ = 0.9(6H, m), 1·9 Bu 1·96(8Η, m), 2.48(6Η· s), 2.76(4H , m>, 3.06(4H, m), 6.55-6.6(6H, m), 6'72(2H, m), 6·78(2Η,m), 7.05~7_07(4H, m), 7.22(2H , m), 7·59(2Η, s), 7·64(2Η, s), 7.8(4H, m) 716.99 716.41 26 95122 201144281 28 δ = 0.9(6H, m), 1.91-1.96(8H, m ), 2.76(4H, m), 3.06(4H, m), 6.55-6.6(6H, m), 6.72(2H, m), 6.95(4H, m), 7.05-7.07(4H, m), 7.51 ( 1H, s), 7.54-7.6(2H, m), 7.77-7.8(5H, m), 8.09(1 H, m), 8.39(1 H, m), 8.82(1 H, m) 739.99 739.39 29 δ = 0.9(6H, m), 1.91-1.96(8H, m), 2.76(4H, m), 3.06(4H, m), 6.6(4H, m), 6.95(4H, m), 7.54(2H, m 7.71 (2H, m), 7.8 (4H, m), 7.87 (2H, m) 696.99 696.43 [Example 1] Manufacture of an OLED device using the organic electroluminescent compound of the present invention using the organic electroluminescent material of the present invention An OLED device was fabricated. First, a transparent electrode ΙΤ0 film (15 Ω / ΙΙΙ) obtained from OLED glass (manufactured by Samsung Corning) was washed with a mixture of trichloroethylene, acetone, ethanol, and distilled water in the order of ultrasonic waves, and stored in isopropyl alcohol for use. Then, the ΙΤ0 substrate was mounted in a substrate holder of a vacuum vapor deposition apparatus. And placing 4,4',4''-tris(卩川-(2-naphthyl)-phenylamino)triphenylamine (2-TNATA) in a chamber of the vacuum vapor deposition apparatus, and then The chamber is vented to a 10 to 6 torr vacuum. A current was applied to the cell to evaporate 2-TMTA, and a hole injection layer having a thickness of 60 nm (nm) was formed on the substrate. Next, Ν,Ν'-bis(α-naphthyl)-indole, Ν'-diphenyl-4,4'-diamine (ΝΡΒ) is placed in another chamber of the vacuum vapor deposition apparatus, A current is applied to the chamber to evaporate the crucible, and a hole transport layer having a thickness of 20 nm is formed on the hole injection layer. After the hole injection layer and the hole are formed, an electric field light-emitting layer is formed on the hole transport layer as follows. The dinaphthyl ruthenium (DM) was placed in a chamber of one of the vacuum gas phase deposition apparatus as a host, and the compound 7 was placed in another 27 95122 201144281 as a dopant. The two materials were evaporated at different speeds, and an electric field luminescent layer having a thickness of 3 〇 nm was vapor-deposited on the hole transport layer at 2 to 5% by weight. Subsequently, tris(8-hydroxyquinoline)aluminum (ni) (Alq) having a thickness of 2 〇 nm was vapor-deposited on the electroluminescent layer as an electron transport layer. Then, an 8-hydroxyquinoline (1) thiumquin〇late having a thickness of 1 nm to 2 nm is deposited in the vapor phase,

Liq) After the electron injection layer, another vacuum vapor deposition apparatus was used to form a (A1) cathode having a thickness of 150 nm to fabricate a ruthenium LED. Each compound used in the OLED was purified by vacuum sublimation at 10-6 (^) t rrrr. Therefore, it has been confirmed that a current of 7.4 milliamperes per square centimeter (mA/cm2) can emit 980 candelas per square meter (cd/m2) of blue light at 7.0 volts (V). [Example 2] A ruthenium Led apparatus was produced in the same manner as in Example [1] except that Compound 15 was added as a dopant material for the electroluminescent layer, and dinaphthyl fluorene (MA) was used as an electroluminescence host. Therefore, it has been confirmed that a current of 9.8 mA/cm 2 (fflA/cm 2 ) can emit 1260 candelas per square meter (cd/m 2 ) of blue light at 7.2 volts (V). [Example 3] An OLED device was produced in the same manner as in Example [1] except that Compound 21 was added as a dopant material for the electroluminescent layer, and dinaphthylquinone (DNA) was used as the electroluminescence host. Therefore, a current of 8.8 milliamperes per square centimeter (mA/cm2) has been confirmed to emit 烛200 candelas per square meter (cd/m2) of blue light at 28 95122 201144281 7.1 volts (V). [Example 4] An OLED device was produced in the same manner as in Example [1] except that Compound 29 was added as a dopant material for the electroluminescent layer, and dinaphthylquinone (DNA) was used as the electroluminescence host. Therefore, it has been confirmed that a current of 9.6 mA/f square centimeter (mA/cm2) can emit 125 Å of candle per square meter (cd/m2) of blue light at 7.2 volts (V). [Comparative Example 1] An OLED device was produced in the same manner as in Example [1] except that Compound A was used instead of the compound of the present invention as a dopant material in a chamber of a vacuum vapor deposition apparatus, and Naphthyl anthracene (DNA) acts as an electric field luminescence host. 〇

The organic electric field luminescent compound of this = is superior to the conventional material. The organic electric field luminescent compound in == is used as a dopant material. The electric field illuminates efficiency while maintaining the same higher color purity. 95122 29 201144281 [Simple description of the diagram] None. [Main component symbol description]

Claims (1)

201144281 VII. Patent application scope: 1. An organic electric field luminescent compound represented by Chemical Formula 1: (1) wherein, An and Ar2 each independently represent a (C6-C30) extended aryl group with or without a substituent, or a (C3-C30) heteroaryl group with or without a substituent; R! To R8 independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl group with or without a substituent, (C6-C30) aryl group with or without a substituent, with or without a substituent ( C3-C30)heteroaryl, (C3-C30)cycloalkyl, cyano, nitro, -NR11R12, _BRl3R214, _PRl5Rl6, _P(=0)Rl7Rl8, Rl9R2〇R2lSi_, R22Y- with or without a substituent (C6-C30) aryl (C-C30) alkyl group with or without a substituent, (C2-C30) alkenyl group with or without a substituent, or with or without a substituent (C2- The C30) alkynyl group, or hydrazine to R8, may each be bonded to an adjacent substituent via a substituted or unsubstituted (C3-C30)alkylene group or a (C3-C30)alkylene group with or without a fused ring. The group is formed to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring, and the carbon atom of the monocyclic or polycyclic aromatic ring formed may be substituted by a gas. Ring A and Ring B independently represent a heterocyclic amino group of 5 to 7 members, and the heterocyclic amine group may be fused to one or more aromatic rings, and may further contain 1 95122 201144281 one or more selected Heteroatoms from NR23, 0, S, and Si R24R25; R11 to R25 independently represent (Cl~c3〇)alkyl group with or without a substituent, (C6-C30) aryl with or without a substituent a (C3-C30)heteroaryl group with or without a substituent, or a core to Rz5, each via a substituted or unsubstituted (C3-C30) alkylene group with or without a fused ring Or (C3-C30) an alkenyl group bonded to an adjacent substituent to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring; Y represents S or 0; and 2. The aryl group may contain one or more A hetero atom selected from the group consisting of B, N, 〇, s, P(=C)) 'Si and p. The organic electroluminescent compound according to claim 1, wherein the substituents Αι, Ar2, Ri to R6, Ru to R25 may be further substituted by one or more substituents selected from the group consisting of 氘: 氘, (c1-C30) alkyl, (C6-C3()) aryl, (C3-C3〇) aryl substituent (C3-C30) with or without dentate substituent a aryl group, a 5- to 7-membered heterocycloalkyl group, a 5- to 7-membered heterocycloalkyl group bonded to one or more aromatic rings, a (C3_C3 fluorene) cycloalkyl group, and a one or more aromatic rings (C6_C3()) ring-based, RaRbR(:sb, (C2_c3〇) alkenyl, (C2-C30)alkynyl, cyano, oxazolyl, _NRdRe, _卯>, PRR, _P(= 〇) RlRk, (C6-C30) aryl (C1-C30) alkyl, (C1-C3G) silk (CM: 3G) aryl, hit-, m♦, 〇) 〇-, silk, nitro and (4); Raj_Rl_ stands for (burning base, (C6-G_based or (10),) hybrid yarn; or 〇ϊ and it (four) is called 3〇) silk, (G1,_recording base, milk 95122 2 201144281 aryl or (C6 -C30) aryloxy group. 3. The organic electric field as described in claim 1 A luminescent compound, wherein the ring A and the ring B are independently selected from the following structures: Z represents a chemical bond, -(CR4lR42)m-, -(R41)C = C(R42)-, -N(R43)_, -S-, -〇-, -Si(R44)(R45)_, -P (R46)-, a p(=〇)(R47)-, -c(=0)- or -B(R48)-; Rai to R48 independently represent hydrogen, gas, halogen, with or without substituents (C1-C30)alkyl, (C6-C30) aryl group with or without a substituent, (C3-C30)heteroaryl group with or without a substituent, with or without a substituent (C3- C30) cycloalkyl, cyano, nitro, -NR11R12, -BR13R214, -PR15R16, -P(=0)Rl7Rl8, RigR2()R2lSi-, Μ-, with or without a substituent (C6-C30) An aryl (C1-C30) alkyl group, a (C2-C30) alkenyl group with or without a substituent, or a (C2-C30) alkynyl group with or without a substituent, or 1^ to R48 may each be via Substituted or unsubstituted (C2-C30)alkylene or (C2-C30)alkylene with or without a slight ring is bonded to an adjacent substituent to form an alicyclic ring, or a monocyclic or polycyclic ring. An aromatic ring, and the carbon atom of the monocyclic or polycyclic aromatic ring formed may be substituted with nitrogen; and m is an integer of 1 to 4. 4. The organic electroluminescent compound according to claim 3, wherein in the group 95122 3 201144281, the ring A and the ring B are independently selected from the following structures: 5. The organic electroluminescent compound according to claim 1, wherein 4 95122 201144281 RpR^R3 and R6 independently represent anthracene, dentate, (C1-C3G) silk with or without a substituent, or (C6-C30) aryl having or. 6. An electrokinetic luminescent compound, as in the scope of claim 3, is selected from the group consisting of the following compounds: 95122 5 201144281 ο An organic electric field light-emitting device comprising the organic electroluminescent compound according to any one of claims 1 to 6. The organic electroluminescent device of claim 7, wherein the first electrode, the second electrode; and one or more layers are interposed in the organic layer of the second electrode and the second electrode; wherein The organic layer comprises = one or more kinds of electric field luminescent compounds as in the scope of the claims to the sixth and the main compound represented by the chemical formula 2 or the formula 3 (A) (3) (3) CArn) c-Ln-(An2)d (Ari3)e-Ll2-(Ari4)f where 95122 6 201144281 Lu represents a (C6-C60) extended aryl group with or without a substituent, or a (C4-C60) heteroaryl group with or without a substituent; L12 represents a fluorenyl group with or without a substituent; To Aru stands independently for hydrogen, deuterium, halogen, (C1-C30)alkyl with or without a substituent, (C6-C30) aryl with or without a substituent, with one or more with or without (C3-C30) aryl group having a substituent (C3-C30) cycloalkyl fused, substituted or unsubstituted (C3-C30) aryl group, with or without a substituent (C3-C30) heteroaryl group, with or without a 5- to 7-membered heterocycloalkyl group of a substituent, a 5- to 7-membered heterocycloalkyl group fused to one or more aromatic rings having or without a substituent, with or without a substituent (C3- C30) cycloalkyl, cyano, nitro, -NRl()lR02, -BRi〇3Ri〇4, -PRl05Rl06, -P(=0)RlG7Rl08, RmRllO RmSi_, R112X-, with or without a substituent ( C6-C30) aryl(C1-C30)alkyl, (C2-C30)alkenyl with or without a substituent, R12 with or without a substituent (C2-C30) alkynyl, R122' 122; or An丨 to Ari4 may each be bonded to an adjacent substituent via a substituted or unsubstituted (C3-C30)alkylene group or a (C3-C30)alkylene group with or without a fused ring. Forming an alicyclic ring, or a monocyclic or polycyclic aromatic ring; ring C and ring D independently represent a (C5-C30) alicyclic ring with or without a substituent, and a (C6-C30) aroma 7 with or without a substituent 95122 201144281 Ring, or (C6-C30) heteroaromatic ring with or without a substituent; Rm to Rm independently represent (CU-C30)alkyl with or without a substituent, with or without a substituent (C6 -C30) aryl, or (C3-C30)heteroaryl with or without a substituent; X represents S or 0; W represents a chemical bond ' _(CRl3lRl32)n-, _(Rl31)C = C(Rl32 )-, -N(Rl33)-, -S_,_0_, _Si (Rl34) (Rl35)-, -P(Rl36)-, _P(=0) (Rl37)_, _C(=0)_ or -B (Rl38)_; Rl21 to Rl23 and Rl31 to Rl38 have the same definitions as Ar" to A; Tl4; the heterocycloalkyl or heteroaryl group may contain one or more selected from B, N, 0, S, P(=0) 'heteroatoms of Si and P; η is an integer from 1 to 3; and c, d, e The organic electroluminescent device of claim 8, wherein the organic layer further comprises one or more selected from the group consisting of an arylamine compound and a styrylaryl group. An amine compound consisting of a group of amine compounds, or a group of one or more organometallics selected from Group 1, Group 2, transition metals of Period 4 and Cycle 5, lanthanide metals, and d-transition elements a metal or complex compound. 10. The organic electroluminescent device of claim 8, wherein the organic layer comprises an electric field luminescent layer and a charge generating layer. 11. The organic electric field light-emitting device according to claim 8, which is an organic electric field light-emitting device that emits white light, wherein the organic layer further comprises a Zen or a plurality of layers simultaneously emitting blue light, red light or green light. An organic electric field luminescent layer of light. 9 95122 201144281 IV. Designated representative map: There is no schema in this case. (1) The representative representative of the case is: ( ). (2) A brief description of the symbol of the representative figure: 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: 2 95122