TW201237137A - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

Abstract

Provided are novel organic electroluminescent compounds and an organic electroluminescent device using the same. More particularly, the organic electroluminescent compound disclosed herein is represented by Chemical Formula 1: wherein A1 through A4, X, Y, Ar1 through Ar3, R1, R2, a and b are the same as defined in the detailed description. Since the organic electroluminescent compound exhibits good luminous efficiency and excellent life property compared to the existing host material, it may be used to manufacture OLED devices having very superior operation life and consuming less power due to improved power efficiency.

Description

201237137 VI. Description of the Invention: [Technical Field] The present invention relates to a novel organic electroluminescent (EL) compound and an organic electric field illuminating device using the same, and more particularly to the use as an electric field luminescent material A novel organic electroluminescent compound and an organic electric field illuminating device using the compound as a host. [Prior Art] The organic EL device is a device in which, when an electric charge is applied to an organic germanium formed between an electron injecting electrode (cathode) and a hole injecting electrode (anode), electrons are paired with a hole and then become a device that is accompanied by light emission and extinction. . The device can be fabricated, for example, as a transparent flexible substrate for plastics. Compared to a plasma display panel or an inorganic EL display, the device can operate at a low voltage (not exceeding 10 V) with relatively low power consumption, but provides excellent color purity. Since an electric field illumination (EL) device can emit three colors (green, blue, and red, which are hereinafter referred to as green, blue, and red light), it has been attracting attention to the full-color color display device of the generation. * In the organic light-emitting diode _D), the most important factor determining the performance including the luminous efficiency and the operational life is the electric field luminescent material. In the functional point, the electroluminescent material can be divided into a host material and a dopant material. In general, excellent EL properties are provided by the electric field luminescence prepared by doping a dopant in a host. Recently, the development of organic EL devices with high efficiency and long operation has become an urgent task. In particular, considering the degree of performance required for medium to large-size GLED panels, it is more advantageous than the development of materials such as the existing electric field 95136 4 201237137, especially the luminescent materials. Technical Problem With the above problems, the compound has luminescence ~ and the device operation, and the material is suitable = the nuclear luminous efficiency of the invention - the purpose is to provide the use of the two:: outstanding skeleton. The organic electroluminescent device of the field illuminating material is used as an electrical technical solution in a general aspect, and the present invention provides an organic electric device and an organic electric device. An organic electric field illuminating device using the compound. The electric field luminescent compound according to the present invention can be used for manufacturing to have a very good operational life < ULED because of its good luminescence efficiency and excellent lifetime properties. Chemical formula 1 J^N, a-<(:3hi vx r2 where ^ to A4 independently represent CR3 or N; X represents -N(R1Q)-, -s 0-, or -Si(R") R12)-; Y represents CR4 or N; ΑΓ-ΑΓι. Ar2 independently represents a (C6-C30) cubic earth with or without a substituent, or a (C3_C3〇) heteroaryl group with or without a substituent, (C6_C3〇) aryl group with or without a substituent, or (C3-C30)heteroaryl group with or without a substituent; 5 to R and h. to .R, 2 independent, 5 95136 201237137 and An Represents hydrogen, deuterium, halogen, (C1-C30)alkyl group with or without a substituent, (C6-C30) aryl group with or without a substituent, and one or more with or without a substituent (C3-C30) a substituted or unsubstituted (c6_a〇) aryl group with a ring-substituted group, a (C3-C30) heteroaryl group with or without a substituent, and 5 members with or without a substituent a 5-membered heterocycloalkyl group, a 5- to 7-membered heterocycloalkyl group fused to one or more aromatic rings having or not having a substituent, and a (C3-C30) cycloalkyl group having or without a substituent And one with or without substituents a plurality of aromatic ring fused (C3-C30) cycloalkyl, cyano, nitro, nr21r22, br23r24, pr25r26, p(=0)R27R28, R2gR3QR3iSi_, R32z_, with or without a substituent (C6-C30 An aryl (C-C30) alkyl group, a (C2-C30) alkenyl group with or without a substituent, with or without a substituent

(C2-C30)alkynyl, ^43 wV; or each of them may be bonded to an adjacent substituent via a (C3-C3G) alkylene group or a (G3-C3()) stretching group with or without a fused ring To form an alicyclic ring, a monocyclic or polycyclic pure, or a monocyclic or polycyclic heteroaryl ring; ring A and ring B independently represent a (C5-C30) cycloalkyl group with or without a substituent, (C6_C3〇)aryl group with or without a substituent, 95136 5 6 201237137 (C6-C30)heteroaryl group with or without a substituent; heart to R32 independently represents (cl_C3〇 with or without a substituent) An alkyl group, a (C6-C3〇)aryl group with or without a substituent, or a (C3-C30)heteroaryl group with or without a substituent; z represents s or 〇; w represents -(CR51R52)ffl -, -(R51)C=C(R52)_, _N(Rs3)_, _s_, -〇-, -Si(R54)(R55)-, _P(R56)_, _p(=())(R57 )_,_c(=〇) or -B(R58)-; the definition of the core to R43 and R51 to r58 is the same as the definition of R丨 to R3; the hetero-alkyl, heteroaryl or heteroaryl ring may contain One or more heteroatoms selected from the group consisting of b, n, 〇, s, p(=0), Si, and P; m represents an integer from 0 to 2; and a and b are independently represented To an integer of 4, and when 2 is greater than 'a and b can be the same or different. [Embodiment] In the present invention, the "burning base", "alkoxy group" and other substituents containing a "alkyl group" include both a straight chain and a branched chain. In the present invention, the ring-based group contains a hydrocarbon such as a polycyclic diamond or a bicyclic group, and a single ring. Further, the * mark in the chemical structure of the present invention means a portion joining the inside of the structure. In the present invention, 'aryl group' means an organic group derived by removing a gas atom from an aromatic hydrocarbon, and may include a 4 to 7 member, an early ring or a fused ring, including one or more chemical bonds. Connect 5 of the aryl groups. Specific examples include phenyl, naphthyl, biphenyl, onion, azide, - 7 95B6 201237137 fluorenyl, phenanthryl, triphenylenyl, fluorenyl, fluorenyl, chrysenyl, thick Naphthacenyl, fluoranthenyl, etc., but are not limited thereto. The naphthalene group includes a naphthyl group and a 2-naphthyl group, and the anthracene group includes a fluorenyl group, a 2-fluorenyl group, and a 9-fluorenyl group, and the fluorenyl group includes a 1-position group, a 2-fluorenyl group, and 3- The base, 4-mercapto and 9~ fluorenyl. In the present invention, "heteroaryl" means one to four hetero atoms selected from B, N, 0, S, P (= 〇), Si and P as an aromatic ring skeleton atom, and The other remaining aromatic ring skeleton atoms are carbon aryl groups. The heteroaryl group may be a 5- or 6-membered monocyclic hydroxy group or a polycyclic heteroaryl group obtained by condensation with a benzene ring, and may be partially saturated. Further, the heteroaryl group includes more than one heteroaryl group bonded by one or more chemical bonds. The heteroaryl group includes a divalent aryl group in which a hetero atom in the ring can be oxidized or quaternized to form, for example, a ruthenium oxide or a quaternary salt. Specific examples include monocyclic heteroaryl groups such as furyl, thienyl, cycloyl, imidazolyl, pyrazolyl'thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, fluorene Azolyl, tridecyl, tetradecyl, morphyl, thiophene, morphine, triazolyl, tetrazolyl, anthracene. a sulfhydryl group, a thiol group, a fluorenyl group, a pyrimidinyl group, a hydrazine group, etc., a polycyclic heteroaryl group, such as a benzofuranyl group, a benzoxanyl group, a benzophenanyl group, a second stupid group Anthracenyl, isopropanylfuranyl, stupid imidazolyl, benzothiazolyl, benzoxanthyl, benzisoxazolyl, benzoxazolyl, isodecyl, fluorenyl, Salivation, stupid and diterpene, quinoline, isoindolyl, cylinyl, olfactory beta, lincoln, 啥 琳 、, ° ° ° sit, base (carborinyl), η non-bite Benzo, benzodioxolyl, etc., N-oxides (such as pyridyl N-95136 8 201237137 oxide, quinolinyl N-oxide, etc.), its quaternary salt, etc., but not Limited to this. The "(C1-C30) alkyl group" disclosed herein may include (d_c2〇) dazzle (base or (C1-C10) alkyl group and "(C6-C30) aryl group" including (C6-C20) Aryl or (C6-C12) aryl. The "(C3-C3〇)heteroaryl" group includes (C3-C20)heteroaryl or (C3-C12)heteroaryl and "(C3-C3〇) The cyclohexyl group includes (C3-C20)cycloalkyl or (C3-C7)cycloalkyl. The "(C2_C30) alkenyl or alkynyl group includes (C2-C20) alkenyl or alkynyl. Or alkynyl group of (C2_C10). In the phrase "substituted or unsubstituted (with or without) substituent" as used herein, the term "substituted" means further substituted unsubstituted substituent. Substituted. Further via Ari & An, Rl to R4, Ri. to Ri2

The substituents substituted with Ru to R32, R41 to R43 and RS1 to R58 may be further substituted with one or more substituents selected from the group consisting of hydrazine, halogen, with or without a dentate substituent; C1_C30) alkyl, (C6_C30) aryl, (C6-C30) aryl with or without (C6-C30) aryl substituent, with or without (C6-C30)heteroaryl substituent (C6_C3 Anthracene, (C3_C3〇)heteroaryl, (C3-C30)heteroaryl, 5- to 7-membered heterocycloalkyl, with or without (C6-C30) aryl substituent, with one or more 5- to 7-membered heterocycloalkyl, (C3_C3())cycloalkyl, fused to one or more aromatic rings (C3-C30) cycloalkyl, NR6iR62, BR63R64, pr65r66, p(=o)r67r68, R69R7oR7iSi_, R72z_, R73c(=〇)_, R74C(=0;)0-, (C2-C30)alkenyl, (C2_C3〇)alkynyl, cyano, carbazolyl, C6-C30) aryl (ci-C3〇)alkyl, (cl_C3〇)alkyl (C6_C3〇) 9 95136 201237137 aryl, carboxyl, nitro and hydroxy, or may be bonded to adjacent substituents to form a ring; ^ to R72 independently represent ((n-C30) alkyl, (C6-C3 0) aryl or (C3-C30)heteroaryl; Z represents S or 0; and R73 and R74 independently represent (Cn-C30)alkyl, (C1-C30)alkoxy, (C6-C30)aryl Or a (C6-C30) aryloxy group. More specifically, the organic electroluminescent compound according to the present invention is selected from the following compounds, but is not limited thereto

Among them, Αγί to An, Y, Ri, R2, Ri. The R12, a, and b are the same as those in the chemical formula 1 of the first application.

10 95136 201237137

*~f *〇 ,-〇 *-〇-〇

•-H

The organic electroluminescent compound may, for example, be the following compounds, but is not limited to such compounds. 11 95136 201237137

12 95136 8 201237137

13 95136 201237137

The organic electroluminescent compound according to the present invention can be produced in the manner shown in Scheme 1 below. [plan 1]

Αι to A4, X, Y, An to An, Ri, R2, a and b are the same as those in Chemical Formula 1. The present invention provides an organic electric field illuminating device comprising a first electrode; 14 95136 201237137 a second electrode; and one or more layers of an organic layer interposed between the first electrode and the second electrode, wherein the organic layer comprises one or A plurality of organic electroluminescent compounds represented by Chemical Formula 1. The organic layer includes an electric field luminescent layer comprising one or more dopants and one or more organic electroluminescent compounds of the chemical formula 1 as a host. The dopant used in the organic electric field light-emitting device of the present invention is not particularly limited, and may be selected from the compounds represented by Chemical Formula 2. Chemical formula 2 MTO. 3 wherein M1 is selected from the group consisting of metals of Group 7, Group 8, Group 9, Group 10, Group 11, Group 13, Group 14, and Group 16, and ligands L1.1, L1() 2 and Lm are independently selected from the following structures:

R213 15 95136 201237137

Rw to R2. 3 independently represent hydrogen (C1-C30) alkyl group with or without a halogen substituent, (C6-C30) aryl group with or without (c, C3〇) a substituent, or A dentate; 'to- independently represents a nitrogen (C1-C3G) alkyl group, with or without a substituent (Cl C3G), with or without a substituent (dG3〇) a cycloalkyl group, with or without a substituent ((4)-(10) with or without a substituent, a mono- or di-(C1-C3G) county amine group, with or without (iv) (tetra)-(C6 -C3G) arylamino group, SF5, tri(n-C3G) ortho (tri(Cl-C3())alkylsilyl) with or without a substituent, with or without a substituent ((3) 〇)alkyl (10)—(10)) a silky group, with or without a substituent of three (10), (d) hydroxy, cyano or dentate, R22. to R223 independently represent hydrogen, singular, oxime & with or without a dentate substituent of: «(10) ice-based, or with or without (8)-(10)-based substituent t; R224 & ^ Α 表示 气 气 气 具有 95 95 95 95 95 136 95 95 95 95 95 95 95 95 95 95 95 95 95 95 95 95 -C30) An alkyl group, a (C6-C30) aryl group with or without a substituent, or a halogen; or Rm and R225 may be via a (C3-C12)alkylene group or a (C3-C12)alkylene with or without a fused ring The group is bonded to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring; R226 represents a (C1-C30) alkyl group with or without a substituent, and a (C6-C30) aryl group with or without a substituent. , having a (C5-C30)heteroaryl group having no substituent, or halogen; Rm to R229 independently representing hydrogen, deuterium, (n-C30)alkyl group with or without a substituent, with or without a substituent (C6-C30) aryl, or halogen; and '233 R234. ^237^23^241^242 r!x232 Q represents, R23SR236 or R239 R240, wherein R231 to R242 independently represent hydrogen, deuterium, or (C1-C30) alkyl group having no halogen substituent, (C1-C30) alkoxy group, halogen, (C6-C30) aryl group with or without a substituent, cyano group, or with or without a substituent (C5-C30) cycloalkyl; or each of them may be attached to an adjacent substituent via an alkyl or alkenyl group to form a spiro or fused ring, or may be attached via an alkyl or an alkenyl group. To R2〇7 or R208 to form a saturated or unsaturated condensed ring dopant compound of Chemical Formula 2 include compounds having the following structures, but not limited to such.

17 95136 201237137

CFS r F, C,

HSC, - the money electronic device towel of the present invention, in addition to the organic electric field luminescent compound, which can be further formed into a group of arylamine compounds and styrene arylamine compounds Or a variety of compounds. The arylamine compound or the styrylarylamine compound is exemplified in Korean Patent Application No. 10-2008-0123276, No. 10-2008-0107606, or No. 10-2008-0118428' but not by the 18 95136 201237137 and so on. Further, in the organic electronic device of the present invention, the organic layer may include, in addition to the organic electroluminescent compound represented by Chemical Formula 1, an organic metal selected from Group 1, Group 2, Cycle 4, and No. 5 One or more metals or complex compounds of the group of periodic transition metals, #1 metal and ^ transition elements. The organic layer may include an electric field luminescence and a charge generating layer. Step by step, the organic layer is in addition to the chemical formula! In addition to the organic electric field luminescent compound, one or more layers of organic electroluminescent layers that emit blue, green or red light may be included to provide an organic electric field illuminating device that emits white light. The compound which emits blue light, green light or red light is disclosed in Korean Patent Application No. 10-2008-0123276, No. i〇_2〇〇8_〇1〇76〇6 and No. 10-2008-0118428 , but not limited to such. In the organic electronic device of the present invention, a layer selected from a chalcogenide layer, a metal-based layer, and a metal oxide layer (hereinafter referred to as a "surface layer") is provided in one of the electrode pairs or On the inner surface of the two electrodes. More specifically, a layer of a metal chalcogenide (including an oxide) of ruthenium or aluminum may be disposed on the anode surface of the electroluminescent luminescent medium layer, and a metal sate layer or a metal oxide layer may be disposed on the luminescent medium layer. On the surface of the cathode. In this way, drive stability can be obtained. The chalcogen compound may be, for example, Si0x (lSxS2), A10x (l$xS1.5), Si〇N, SiA10N, or the like. The metal halide may be, for example, LiF, MgF2, 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. 19 95136 201237137 彳 In an organic electric field illuminating device, it is preferable to arrange a mixture of an electron transporting compound and a reducing dopant or a mixture of oxidative conjugates of a hole transporting compound (4) on at least one inner surface of the electrode pair. Since the electron transporting compound is reduced to an anion, it is easier for the electrons to be injected and transported to the electric field illuminating medium from the mixing region. Furthermore, since the hole-passing compound is oxidized to a cation, it becomes easier to inject and transport the hole from the mixed region to the electric field illuminating medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds. Preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. Further, an electric field emitting device that emits white light having two or more layers of an electroluminescent layer can be prepared by using a reducing dopant layer as a charge generating layer. [Advantageous Effects] Since the organic electroluminescent compound according to the present invention exhibits good light-emitting efficiency and excellent lifetime properties, it can be used to manufacture an OLED device having a very excellent operational life. Mode of the Invention The present invention will further explain the luminescent properties of the organic electroluminescent compound of the present invention, the method of preparing the compound, and the apparatus using the compound. However, the following specific examples are merely illustrative and are not intended to limit the scope of the invention. [Preparation Example 1] Preparation of Compound 2 20 95136 5 201237137

Preparation of compound 1-1 3-bromothiophene (50 g, 306 mmol) was dissolved in THF (300 mL) and toluene (1,200 mL). The mixture was cooled to _78 ° C, and n-BuLi (150 mL, 2.5 M) was added thereto. In hexane, 367 mmol). After the mixture was stirred for 1 hour, triisopropyl borate (112 mL, 490 mmol) was added while maintaining the temperature at -78 °C. The mixture was stirred for 10 minutes. Upon completion of the reaction, water was added and the mixture was extracted with EA/water. After removing the water with MgS〇4, distillation was carried out under reduced pressure, and the compound l-l (24 g, 60%) was obtained by separation through a column (di-methane (MC) / hexane). Preparation of Compound 1-2 Compound 1-1 (20.62,161111111〇1), 2-bromonitrobenzene (25 liters, 124 mmol), Pd2dba3 (1. lg, 1.2 mmol), X-phos (2.4 g, After 5 ramol) and K3P〇4 (79 g, 370 mmol) were dissolved in 1,4-dioxin (3 〇〇mL), the mixture was stirred under reflux for one day. Upon completion of the reaction, the mixture was cooled at room temperature and extracted with EA/HA. After removing the water with MgS 4 , distillation was carried out under reduced pressure, and Compound 1-2 (23.5 g, 92%) was obtained by separation from a column (MC/hexane). Preparation of Compound 1-3 Compound 1-2 (22.5 g, llO mmol) was dissolved in p(〇Et)3 (500 mL) 21 95136 201237137 and then stirred under reflux for 4 hours, and P(0Et)3 was removed by distillation to obtain red liquid. Compound l-3 (6 g, 31%) was obtained by subjecting the red liquid to a column (EA/hexane). Preparation of compound 1-4 2,4,6-trisole (10舀, 54.51111111〇1), phenylboronic acid (16.6g, 136, 29mmol), Pd(PPh3)4 (3. 15g 2·72 mmol), 2M K2C 3 (50 mL), toluene (100 mL) and ethanol (30 mL) were stirred under reflux. After 4 hours, the mixture was cooled to room temperature and extracted with EA after addition of water. After dehydrating with MgSCh, it was evaporated under reduced pressure, and Compound l-4 (7 g, 48···) was obtained by column separation. Preparation of compound 2

NaH (1.57 g, 39.36 mmol, 60% in mineral oil) was added to dmf (70mL), and compound i-4 (7 g, 26.24 mmol) was dissolved in dmf (60mL). After 1 hour, the compound uasg, 2l 87 min 〇 1) was dissolved in DMF (7 mL). After the mixture was stirred for 1 hour, distilled water was added and the mixture was extracted with EA. After dehydration with MgS 4 , it was distilled under reduced pressure, and Compound 2 (7 g of 56%) was obtained by column separation. [Preparation Example 2] Preparation of Compound 17 95136 22 201237137

Preparation of compound 2-1 Compound 1-3 (5.3 g, 30.6 roni〇l), 4-iodobromobenzene (17.3 g, 61 mmol), Cu (2.9 g, 46 mmol), 18~ crown-6 (〇) After 8 g, 3 mmol) and k2C 3 (12 g, 72 mmol) were dissolved in 1,2-dichlorobenzene (35 mL), the mixture was stirred at < When the reaction element was formed, Cu and base were removed using cel 1 ite and the solution was extracted with EA/H 2 。. After dehydration of the mash of the basket, it was evaporated under reduced pressure to give the compound 2-l (5 g, 50 ° /.). Preparation of compound 2-2 Compound 2-l (4 g, 12 mmol) was dissolved in THF (6 () mL), the mixture was cooled to -78 ° C, and n-BuLi (5 8 mL, 2. Medium, 14. 4mino 1). After the mixture was stirred for 1 hour, triisopropyl carboxylate (4 mL, 19.2 mmol) was added. After slowly increasing the temperature, the mixture was stirred at room temperature for one day. Upon completion of the reaction, 2MHC1 was added and the mixture was extracted with EA/H2. After removing the water with MgS 4 , the mixture was evaporated under reduced pressure, and compound 2-2 (2·g, 60%) was obtained by column (MC/hexane). Preparation of compound 2-3 1,3-dibromobenzene (11.2 g, 47 mmol) After dissolved in THF (200 mL), 95136 23 201237137 The mixture was cooled to -78 °C. After n_BuLi (19 mL, 2.5 Μ in hexane, 70. 5 mmol) was slowly added, the mixture was stirred for 1 hour. A solution of TPS-Cl (20 g' 56-8 mmol) dissolved in THF (25 mL) was slowly added. After slowly increasing the temperature, the mixture was stirred at room temperature for one day. Upon completion of the reaction, hydrazine was added and the mixture was extracted with hydrazine/hydrazine. After removing water with MgS 4 , distillation was carried out under reduced pressure, and Compound 2-3 (17 g, 87%) was obtained by separation from a column (MC/hexane). Preparation of Compound 2-4 Compound 2-3 (17.3 g, 41.8 mmol) was dissolved in THF (200 mL) and the mixture was cooled to -78. The n-BuLi (20 mL, 2.5 M in hexane, 5 Οππηο 1) was slowly added and the mixture was shaken for 1 hour. Tridecyl borate (7 mL, 67 mmol) was slowly added thereto and the temperature was slowly increased. The mixture was stirred at room temperature for one day. Upon completion of the reaction, 2MHC1 was added and the mixture was extracted with EA/H2. After removing the water with MgS 4 , distillation was carried out under reduced pressure, and Compound 2-4 (10.5 g, 66%) was obtained by separation from a column (MC/hexane). Preparation of compound 2-5 Compound 2-4 (5 g, 13 mmol), 2,4-di-pyrimidine (1.8 g, 12 mmol), pd (pph3) 4 (0.7 g, 0.6 mmol) and Na2C〇3 (2.5 g, After 24 mmol), the mixture was dissolved in benzene (90 mL), EtOH (30 mL) and H.sub.2 (12 mL). Distillation was carried out under reduced pressure, and the compound 2-5 (5 g, 93%) was obtained by separation from a column (MC/hexane). Preparation of compound 17 Compound 2-2 (2 g, 6.8 mmol) -5 (2. 8g, 6. 2 24 95136 8 201237137 mmol), Pd(PPh3) 4 (0.3 g, 0.3 mmol) and Na2C〇3 (1.4 g, 12.5 mmol) were dissolved in toluene (50 mL), Et0H ( After 15 mL) and H2 hydrazine (6 mL), the mixture was stirred at 100 ° C for one day. Upon completion of the reaction, the mixture was extracted with EA/H 2 hydrazine. The water was removed with MgS 4 and then distilled under reduced pressure. (2 g, 60%) was obtained by separation from a column (MC/hexane). Compounds 1 to 68 were prepared according to the methods of Preparation Examples 1 and 2. 1H NMR and MS/ of the organic electroluminescent compound thus prepared. The data for FAB is provided in Table 1. 25 95136 201237137 Table 1 NMR (CDC13, 200 MIfe) - MS/FAB Measured value. m), 7.51-7.52(8H, m), 7.88(1H, ra):, 7.94(1H, oi), 8.05(2H, m), 8.55(1H, m) 4-01,52 401.12 2 δ = 6.960 J], m), 7.2-7,25(2H, id), 7.33Π.Η, m), 7.4K2H, ffl), 7.51.(4H, m), 7.94(1H, in), 8.28(4H, m), 8.55 (.1H, m) 404.49 404.11 3 δ = 6.96C1H, id), 7.2-7,25(2H> m), 7.32(1H, s)f 7.33C1H, m), 7.4K2H, m) t 7.5K4H, m), 7.79(2H, m), 7.94(1H, m), 8.28(2H, ra), S.55(1H, m) 403.50 403.11 4 δ = 6.96(1H, m), 7.2- 7.25(2H, m), 7.33(1H, m), 7.4K2H, m), 7.5K.4H, m), 7.79(4H.m), 7.94(1H, m), 8.55(1H, m), 8.63 (1H, s), (H,) 403.50 403.11 5 δ = 6.96-7(3H, ra), 7.2-7.26(4H; m), 7.33(1H, m), 7.5K2H, m), 7.:94 (1H, id), 8.5-8.55(3H, m), 8.62(2H, m), 8.9(1H, ra) 403.50 403.11 6 δ = 6.96(1H, m), 7.1K1H, m), 7.2-7.25C2H , m), 7.33C1H, in), 7.41-7.54(8H, m), 7.94(1.H, m), 8.3(2H, m), 8.55-8.fi(2H, m) 402.51 402.12 7 δ = 6.96(1H, m), 7.2-7.25(10H, ra), 7.33(1H, m), 7.4K2H, m), 7.51-7.52(8H, m), ?.88(1H, m), 7.94(1H, m), 8.05(2H, m), 8.55(1H, m) 553.71 553.15 8 δ = 1.72(12H, s), 6.96C1H, m), 7:2-7.38(7H, m), 7.55(2H, m), 7,63(2H, m), 7.77m, m), 7.87-7.94(6H, m) , 8.05(2H, m), 8.55(lH, m) 633.84 633.25 9 δ = 1.72(6H, s), 6:96(1H.m), 7.17-7.25(3H, m), 7.33-7.34(2H, m). 7.4K2H, m), 7.51-7.56(5H, m), 7.63(1H, m), 7.87-7...94(3H, m), 8.28C4H, m), 8.55(1H, m) 596.74 596.20 10 δ = 6.96(1H, in), 7.2-7.25C4H, m), 7.33(1H, ra), 7.4U2H, m), 7.5K4H, ra), 7.68C2H, m), 7.79-7.85(8H , ra), 7.94(1H, m), 8.23(1H, s), 8.55(1H, m) 555.69 555.18 11 δ = 6.96(1H, m), 7.2~7.26(3H, m), 7.33-7.4K3H, m), 7.5'7.52(5H, ui), 7.88(2H, ra), 7.94(LH, m), 8.55C.1H, m), 8.8K2H, m) 402.51 402.12 12 5 = 6.96(1H, ra) , 7.2-7.25(2H, m), 7.33C1H, m), 7.4K1H, m), 7.51-7.52C4H, m), 7.6C1H, m), 7.62C1H, s), 7.78C1H, ra), 7.88( 2H, m), 7.94-7.98(2H, m). 8.22(1H, m), 8.55(JH.m), 8.81.(2H, m) 452.57 452.13 13 δ = 6,96( 1H, m), 7.2 -7.25(4H, m), 7.33(1H, m), 7.4K1H, m), 7.51-7.52(4H, m), 7.8-7.85(3H, ra), 7.94(1H, in), 8.05-8.06(2H, m), 8.16C1H, mL 8.55(1H, m) 453.56 453.13 14 δ = 6.96(111, m), 7.2-7.25 (2H, ra), 7.33~7.37(7H, m), 7.46-7.55(.14H, m), 7.89-7.94(3H, m), 8.09(1H, m.), 8.55(1H, m) 583.82 5ώ .1δ 15 δ = 6,96(1H, ra), 7.2-7.25(2H, ra), 7.33-7.37(7H, m)t 7.46-7.55(llHt id), 7.89-7,96(4H, m) , 8.55-8.57(2H, m) 585.79 585.17 16 δ = 6.96(1H, m), 7.2-7.25(2H, ra), 7.33-7.55(21H, m), 7.89-7.94(3H, m), 8.28( 2H, m), 8.55C1H, m) 662.88 662.20 17 δ = 6.96(1H, m), 7.2-7.25(211, m), 7.33-7.46(14H, m), 7.55-7.6K5H, m), 7.68( 2H, m), 7.76-7.79(3H, m), 7.89-7.94(2H, m), :8.29(1H, m), 8.55C1H, m) 661.89 661.20 18 δ = 6.96(1H, m), 7.2- 7.25C2H, m), 7.33-7.4K3H, m), 7,,51(2H, m), 7.85(1H, in), 7.94C1H, ra), 8.28Γ2Η, m), 8.38C1H, ra), 8.55 -8.59(2H, m) 405.47 405.10 19 δ = 6.96C1H, m), 7.2-7.25(2H, ra), 7.33C1H, m), 7.55(4fl, m), 7.6K2H, m), 7.94-7.95 ( 3H, m), 8.04-8.08(4«, m), 8.55C3H, m)... 504.60 504.14 20 δ = 6.96(1H, m), 7.2-7.25(2H, m), 7.33(1H , m), 7-59 ( 4H, ra), 7.92-8(7H, m), 8.49(2H, m), 8.55(1H, m), 9.09(2H, m) 504.60 504.14 21 5 = 6.96(1H, m), 7.2-7.25( 2H, ra)., 7.33C1H, m), 7.6(2H, m), 7.78(2H, m), 7.94~7.98(3H, m), 8.06C2H, m), 8.22(2H, m), 8.55- 8.57(3H, m) 506.58 506.13 22 δ = 6.96(1H, m), 7.2-7.25(2H, m), 7.33C1H, m), 7.67(4H, m), 7.8(4H, 508.56 508.12 26 95136 8 201237137 m), 7.94(1H, m), 8.55(1H, m), 8.7(2H, s), (H,) 23 δ = 6.96(1H, m), 7.2-7.33(4H, m), 7.41-7.51 (10H, m), 7.67(1H, in), 7.94(1H, m), 8.06(1H, m), 8.55C1H, m) 453.56 453.13 24 δ = 6.96(1H, m), 7.2-7.25(2H, (m), 7.33 (1H, m), 7.4K2H, m), 8.55(1H, m) 479.59 479.15 25 δ = 7.25(2H, s), 7.25(0H, ra), 7.33C1H, ra), 7.4K3H, m), 7.5K6H, m), 7.79(2H, m), 7.94(1H, m), 8.28(4H, m), 8.55(1H, m) 480.58 480.14 26 δ = 6.96C1H, m), 7.2-7.25C2H, m), 7.33C1H, m), 7.4K2H, ra) , 7.51-7.52(8H, m), 7.66(3H, m), 7.94(1H, ra), 8.55(1H, m), 9.42(2H, m) 479.59 479.15 27 δ = 6.96(1H, ra), 7.2 -7.25(2H, m), 7.33(1 H, m), 7.36 (1H, s), 7.41-7.42 (3H, m), 7.51-7.52 (4H, m), 7.62 (4H, m), 7.7K1H, m), 7.94 (1H, m), 8.17(1H, m), 8.55(1H, m) 440.56 440.13 28 5 = 6.96(1H, m), 7.2-7.29(4H, m), 7.32(1H, s), 7.33(2H, m), 7.4K1H , m), 7.5-7.5K3H, m), 7.63~7.68(3H, m), 7.79(4H, m), 7.94(2H, m), 8.12(1H, m), 8.55C2H, m) 568.69 568.17 29 δ = 6.96(1H, ra), 7.2-7.25(3H, m), 7.33C2H, m), 7.63-7.67(4H, m), 7.8(1H, m), 7.94(2H, m), 8.05-8.06 (2H, m), 8.16(2H, m), 8.54-8.55(3H, m) 516.61 516,.14 30 5 = 6.96(1H, m), 7.16(1H, s), 7.2-7.33(9H, m ), 7.5(2H, ra), 7.63-7.68(4H, m), 7.79C2H, m), 7.94(3H, m), 8.12(2H, m), 8.55(3H, m) 657.78 657.20 31 δ = 6.96 (1H, m), 7.2-7.33(6H, m), 7.45-7.5(7H, ra), 7.58-7.63(5H, m), 7.69C1H, m), 7.77(2H, m), 7.87-7.88C2H , m), 7.94-8.05C5H, ra), 8.12(1H, m), 8.18(1H, m), 8.55(2H, ra) 731.90 731.24 32 δ = 6.96(1H, m), 7.2-7.25(2H, m), 7.33(1H, m), 7.57(1H, m), 7.67(4H, m), 7.8(1H, m), 7.94-7.96(3H, m), 8.05-8.16(6H, m), 8.51 -8.55(3H, m) 566.67 566.16 33 δ = 6.96(1H, m), 7.2(1H, in), 7.4 K3H, m), 7.51~7.52(8H, m), 7.68(2H, m), 7.77-7.79(7H, ra), 8(1H, m), 8.18(1H, m), 8.23(1H, s) , (H,) 555.69 555.18 34 δ = 6.96(1H, in), 7.2-7.33(4H, m), 7.4K2H, m), 7.5-7.51(5H, m), 7.62-7.68(4H, m), 7.79(6H, m), 7.94-7.98(3H, ra), 8.12(1H, ra), 8.23(1H, s), 8.55(1H, m) 644.78 644.20 35 δ = 6.96(1H, m), 7.2- 7.25C2H, m), 7.33C1H, m), 7.41-7.5K8H, m), 7.79(4H, m), 7.94(1H, m), 8.09(1H, m), 8.23(1H, s), 8.28( 1H, m), 8.55(1H, ra) 479.59 479.15 36 δ = 1.48(6H, m), 1.73C4H, m), 2.72(1H, m), 6.95-6.96(2H, m), 7.2(1H, m ), 7.4K2H, m), 7.5K4H, m), 7.68(2H, m), 7.79(6H, m), 7.86(1H, m), 8.23(1H, s), 8.79(1H, m) 561.74 561.22 37 δ = 6.96C1H, m), 7.06(1H, m), 7.2(1H, m), 7.4K2H, m), 7.5K4H, m), 7.68(2H, ra), 7.79(6H, m), 7.92 (1H, m), 8.22(1H, m), 8.23(1H, s), (H,) 497.58 497.14 38 δ = 3.05(2H, m), 4.14C2H, m), 6.06(1H, m), 6.55 (1H, m), 6.72(1H, m), 6.96(1H, m), 7.05~7.07(2H, m), 7.2-7.25(2H, m), 7.33(1H, m), 7.68(2H, m ), 7.79-7.83(3H, m), 7.94C1H, m), 8.55(1H, m) 444.55 444.14 39 δ = 6.9 6(2H, m), 7.2~7.25(4H, m), 7.33(2H, m), 7.68(4H, m), 7.79(4H, m), 7.94(2H, m), 8.55(2H, m) 496.64 496.11 40 δ = 1.72C6H, s), 6.55C2H, m), 6.69-6.73(4H, m), 6.96-7.05(5H, m), 7.2-7.25(2H, ra), 7.33(1H, m) , 7.54(2H, m), 7.68(2H, m), 7.79(2H, m), 7.94C1H, m), 8.55(1H, m) 532.70 532.20 41 δ = 6.96(1H, m), 7.2-7.25 ( 2H, m), 7.33(1H, m), 7.41~7.52(8H, m), 7.58C2H, in), 7.68(2H, m), 7.79(2H, m), 7.92~7.94(2H, m), 8.07(1H, m), 8.28(1H, m), 8.55(1H, m) 517.64 517.16 42 δ = 0.66(6H, s), 6.69-6.73(6H, ra), 6.96(1H, m), 7.2- 7.33(7H, m), 548.77 548.17 27 95136 201237137 7.54(2H, m), 7.68(2H, m), 7.79(2H, ra), 7.94(1H, m), 8.55(1H, m) 43 δ = 1.16 C2H, m), 1.48C2H, m), 1.58(2H, m), 1.73C2H, ra), 2.95C2H, in), 6.52(1H, m), 6.66-6.69(3H, m), 6.96(1H, m), 7.05-7.08(2H, m), 7.2-7.25C2H, ra), 7.33(1H, ra), 7.57(2H, m), 7.68C2H, m), 7.79(2H, m), 7.94(1H , m), 8.55(1H, m) 496.66 496.20 44 δ = 6.96(1H, m), 7.2'7.25(3H, ra), 7.33(1H, m), 7.67-7.68(6H, m), 7.79(4H , m), 7.94-7.97(4H, m), 8.16(1H, ra), 8.43(1H, m), 8.54-8.55(2H, m) 541.66 541.16 45 δ = 6.59(2H, in), 6.69C2H, m), 6.77(2H, m), 6.89-6.96(5H, m), 7.2 -7.25(2H, ra), 7.33(1H, m), 7.54(2H, m), 7.68C2H, m), 7.79(2H, m), 7.94(1H, m), 8.55(1H, m) 506.62 506.15 46 δ = 6.69(2H, m), 6.96-6.97(3H, m), 7.16-7.25(8H, m), 7.33(1H, m), 7.54C2H, m), 7.68(2H, ra), 7.79C2H , m), 7.94(1H, in), 8.55(1H, m) 522.68 522.18 47 δ = 6.38(4H, m), 6.56(4H, m), 6.63(2H, m), 6.69C2H, m), 6.8 K1H, m), 6.96(1H, m), 7.2-7.25(4H, m), 7.33C1H, m), 7.54(2H, m), 7.68(2H, m), 7.79(2H, m), 7.94( 1H, m), 8.55(1H, m) 581.73 581.19 48 δ = 2.88(4H, ra), 6.58(2H, m), 6.69(2H, m), 6.76(2H, m), 6.96~7.04(5H, m), 7.2-7.25(2H, ra), 7.33(1H, m), 7.54(2H, ra), 7.68(2H, m), 7.79(2H, m), 7.94(1H, m), 8.55(1H , ra) 518.67 518.18 49 δ = 6.63C2H, m), 6.69(2H, ra), 6.8K2H, m), 6.96-7.05C5H, m), 7.2-7.25(4H, m), 7.33(1H, m) , 7.54(2H, m), 7.68(2H, m), 7.79C2H, m), 7.94(1H, m), 8.55(1H, ra) 516.65 516.17 50 δ = 6.69(4H, m), 6.87(2H, m), 6.96(1H, m), 7.16-7.25(4H, m), 7.3 3C1H, m), 7.47(2H, m), 7.54C4H, m), 7.68(2H, ra), 7.79-7.85(4H, m), 7.94(1H, m), 8.55(1H, m) 566.71 566.18 51 δ = 6.96(1H, m), 7.2-7.33(6H, m), 7.46-7.52(4H, m), 7.63-7.68(3H, m), 7.79(2H, m), 7.94(2H, m), 8.09-8.12(2H, m), 8.55(2H, ra) 490.62 490.15 52 δ = 6.96(1H, m), 7.2-7.25(7H, m), 7.33(2H, m), 7.45-7.5(3H, m ), 7.58(2H, m), 7.68-7.69(3H, m), 7.77-7.79(3H, m), 7.87(1H, m), 7.94(2H, m), 8.55(2H, m) 566.71 566.18 53 δ = 6.96C1H, m), 7.2-7.33(6H, m), 7.4K1H, ra), 7.5-7.5K3H, ra), 7.63-7.68(5H, m), 7.79C6H, m), 7.94(2H, m), 8.12(1H, m), 8.23C1H, s), 8.55(2H, ra) 644.78 644.20 54 δ = 6.96(1H, m), 7.2-7.25(2H, ra), 7.33(1H, m), 7.4K2H, m), 7.48-7.5K5H, m), 7.57(1H, m), 7.68-7.7C3H, m), 7.79C2H, m), 7.94(1H, m), 8.24-8.28(5H, m) , 8.55(1H, ra) 556.68. 556.17 55 δ = 6.96(1H, m), 7.2-7.25(2H, ra), 7.33(1H, m), 7.4K3H, m), 7.51-7.52(8H, m) , 7.66-7.68(5H, ra), 7.79C4H, m), 7.94(1H, ra), 8.23(1H, s), 8.28(2H, m), 8.55(1H, m) 631.79 631.22 56 δ = 7.25( 1H, m), 7.33(1H, m), 7.41-7.42(3 H, in), 7.5K4H, m), 7.79(4H, m), 7.94(1H, m), 8.13(1H, m), 8.55(1H, m), 8.63(1H, s), (H,) 387.43 387.14 57 δ = 7.25(lHt m)t 7.33^-7.55(19H, m), 7.89'7.96(4H, m), 8.13C1H, m)( 8.55-8.57(2H, m) 569.73 569.19 58 δ = 7.250 H, ra), 7.33(1H, m), 7.41~7.42(3H, m), 7.5K4H, m), 7.68(2H, m), 7.79-7.85(8H, m), 7.94(1H, m), 8.13(1H, m), 8.23(1H, s), 8.55(1H, m) 539.62 539.20 59 δ = 0.14(6H, s), 5.2(1H, m), 6.6(1H, m), 7.25C2H, m ), 7.4K2H, m), 7.51-7.54(5H, ra), 7.68(2H, m), 7.79(6H, ra), 8.23(1H, s), 8.4(1H, m) 505.68 505.20 60 δ = 0.14 (6H, s), 5.2(1H, m), 6.6(1H, m), 7.25(2H, m), 7.4K2H, ra), 582.77 582.22 28 95136 8 201237137 7.48-7.57(7H, m), 7.68- 7.7C3H, m), 7.79(2H, m), 8.24-8.28(5H, m), 8.4(1H, m) 61 δ = 0.14(6H, s), 5.2(1H, m), 6.6(1H, m ), 7.25(2H, m), 7.4K2H, m), 7.51-7.54(9H, m), 7.85(4H, in), 8.3(4H, m), 8.4(1H, m), 8.63(1H, s ), (H,) 581.78 581.23 62 δ = 6.19(1H, m), 7.25-7.26(2H, m), 7.33(1H, m), 7.41-7.5K9H, m), 7.58(2H, m), 7.79 (4H, m), 7.94(1H, in), 8.55(1H, m), 8.63C1 H, s), (H,) 462.54 462.18 63 δ = 6.19(1H, m), 7.25-7.26(2H, ra), 7.33(1H, m), 7.41~7.52(14H, m), 7.58(2H, m), 7.66-7.68(5H, m), 7.79(4H, m), 7.94(1H, m), 8.23(1H, s), 8.28(2H, m), 8.55(1H, m) 690.83 690.28 64 δ = 6.19(1H, m), 7.25-7.26(2H, ra), 7.33(1H, m), 7.41-7.5K9H, m), 7.58(2H, m), 7.68(2H, m), 7.79(6H, m), 7.94(1H, m), 8.23(1H, s), 8.55(1H, ra) 538.64 538.22 65 δ = 6.19(1H, m), 7.25-7.26(7H, m), 7.33(2H, m) , 7.45-7.5(6H, ra), 7.58(4H, m), 7.68-7.69(3H, m), 7.77-7.79(3H, m), 7.87(1H, m), 7.94(2H, m), 8.55 C2H, m) 625.76 625.25 66 δ = 2.06OH, m), 7.25(1H, m), 7.33(1H, m), 7.41~7.52(12H, m), 7.58(2H, m), 7.66-7.68(5H , m), 7.79(4H, m), 7.94(1H, m), 8.23(1H, s), 8.24-8.28(4H, m), 8.55(1H, m) 705.85 705.29 67 δ = 2.06(3H, m ), 7.25(1H, m), 7.33(1H, m), 7.41-7.5K7H, m), 7.58(2H, m), 7.68(2H, ra), 7.79(6H, m), 7.94(1H, m ), 8.23(1H, s), 8.24(2H, m), 8.55(1H, ra) 553.65 553.23 68 δ = 2.06(3H, m), 7.25(6H, m), 7.33C2H, m), 7.4-7.5 (5H, m), 7.58C2H, m), 7.68-7.69(3H, m), 7.77-7.79(3 H, ra), 7.87 (1H, m), 7.94C2H, m), 8.42 (2H, m), 8.55 (2H, in) 641.76 641.26 [Example 1] OLED device using an organic electroluminescent compound according to the present invention Manufacture The OLED device is fabricated using the organic electroluminescent compound of the present invention. First, a transparent electrode ΙΤ0 film (15 Ω / ΕΙ) prepared by a glass substrate for OLED (manufactured by Samsung Corning) was ultrasonically washed with trichloroethylene, acetone, ethanol, and distilled water, and stored in isopropyl alcohol. . Then, the ΙΤ0 substrate is assembled in a substrate holder of a vacuum vapor deposition apparatus, and 4,4',4"-parameter (Ν,Ν-(2-naphthyl)-phenylamino)triphenylamine (2-ΤΝΑΤΑ) Placed in a cell of the vacuum vapor deposition apparatus, and then ventilated the chamber to a 10-6 torr vacuum. Subsequently, a current is applied to the chamber to evaporate 2-TNATA, whereby ΙΤ0 substrate shape 29 95136 201237137 into a hole injection layer with a thickness of 60 nm (nm). Subsequently, N,N'-bis(α-naphthyl)-N,N,_diphenyl-4,4 The -diamine (NPB) is placed in another chamber of the vacuum vapor deposition apparatus, and a current is applied to the chamber to evaporate the NPB, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer. > After the hole injection layer and the hole transport layer, an electric field light-emitting layer is formed thereon in the following manner. The compound 3 is placed in a chamber of a vacuum vapor deposition apparatus as a host material, and Ir(PPy) ) 3 [parameter (2_phenyl. ratio) 铱]) is placed in another chamber as a dopant. The two materials are evaporated at different rates to make An electric field light-emitting layer having a degree of 30 nm is vapor-deposited on the hole transport layer by doping 4 to 1% by weight. Subsequently, a para-hydroxyquinoline aluminum having a thickness of 2 〇 nm is vapor-deposited on the electric field light-emitting layer. (III) (A1q) as an electron transport layer. Subsequently, lithium quinolate (Liq) having the following structure having a thickness of 1 nm to 2 nm is deposited as an electron injection layer, and another vacuum gas phase is used. The deposition apparatus was used to form an aluminum (A1) cathode having a thickness of 150 nm to produce a ruthenium LED. The compound was used for purification by vacuum sublimation using a 0 LED. As a result, it was confirmed that a current of 3. 7 mA/cm 2 was circulated at 6.8 V volts. Green light of 1060 cd/m 2 was emitted. [Example 2] In addition to the electric field luminescent layer, compound 34 was added as a host material and Ir(ppy) 3 [parameter (2-phenylpyridine) ruthenium] was used as an electric field luminescent dopant. The 〇LED device was fabricated in the same manner as in Example 1. 95136 30 201237137 5 V volts was passed and the result was confirmed, and a current of 3.5 mA/cm 2 was confirmed to be 6.10 cdcd/m 2 of green light. [Example 3 Adding compound 51 as a host material in addition to the electroluminescent layer A 〇LEd device was produced in the same manner as in Example 1 except that Ir(ppy)3[?(2-phenylacridine)铱]) was used as the electric field luminescence conversion. Further, it was confirmed that 3.9 mA/cm 2 was used. The current was discharged at a green light of 1070 cd/m 2 at 6.9 V. [Example 4] In addition to the addition of the compound 13 as a host material to the electroluminescent layer, (Pid) 2lr(acac) [double-(i-phenyl)淋基) Silver α B = 丙刚的]) In addition to the electric field Wei _, the OLED is manufactured in an actual manner. As a result of the η phase, it was confirmed that a current of 13.8 mA/cm 2 was emitted at 7.120 cd/m 2 of red light. [Example 5] In addition to the addition of the electric field luminescent layer (Pid)dr (acac) [double, (as a host material and ugly]) as the electric green 1 base) silver (ΠΙ) B In the same manner as in Example 1, except for producing gLEd _, the same method as in Example 1 was issued (10) 5 cd/m::: [Comparative Example 1]

In addition to 4, 4,-di (carbazole Q sitting ~ 9 ~ base) - biphenyl (CBP) instead of the 95136 201237137 vapor deposition apparatus of the present invention - the host material in the chamber and double ratio repair]) as a hybrid The coffee was produced in the same manner as in Example i except that the phenyl hydrazine (1) (10) (8) was a hole blocking layer. As a result, it was confirmed that a current of 3. 8 mA/cm 2 was flowed at 7. 5 volts and a green light of 1000 cd/m 2 was emitted. [Comparative Example 2] except that 4'4'-bis(carbazol-9-yl)-biphenyl (CBP) was used instead of the compound of the present invention as a host material in a chamber of a vacuum vapor deposition apparatus and used (piq) 2Ir(acac)[bis-(1-phenylisoquinolinyl)indole (indole) acetamidine]) as a dopant and using bis(2-indenyl-8-hydroxyquinolyl) (pair A ruthenium LED was produced in the same manner as in Example 1 except that -phenylphenolic)aluminum (lUXBAiq) was used as the hole barrier layer. As a result, a current of 15.3 mA/cm 2 was confirmed to flow at 7.5 V volts and a red light of 1000 cd/m 2 was emitted. The organic electroluminescent compound according to the present invention has excellent properties compared to conventional materials. Further, the apparatus using the organic electroluminescent compound according to the present invention as a host material has excellent electric field luminescent properties and lowers the driving voltage, thereby increasing power efficiency and improving power consumption. [Simple description of the diagram] None [Key component symbol description] None 95136 32

Claims (1)

201237137 . VII. Patent application scope: 丨. An organic electric field luminescent compound, which is represented by the chemical formula: JL^N—(AriJa—Arf Rl-Oi R2 γ*Α 1 where Ai to A4 independently represent CR3 Or N; X represents -N(R1Q)-, -S-, -〇-, or -Si(Ru)(Rl2)_; Y represents CR4 or N; An and An independently represent with or without a substituent (C6-c3〇) an aryl group, or a (C3_C3〇)extended heteroaryl group having or without a substituent, and Αι*3 representing a (C6-C30) aryl group having or not having a substituent, Or a (C3-C30)heteroaryl group having no substituent; Ri to fluorene and heart to R!2 independently represent hydrogen, deuterium, halogen, (C-C30) alkyl group with or without a substituent, having or a (C6-C30) aryl group having no substituent, a substituted or unsubstituted (c6_c3〇) aryl group fused to one or more (C3-C30) ring-based groups having or not having a substituent, (C3_C3〇)heteroaryl group with or without a substituent, 5- to 7-membered heterocycloalkyl group with or without a substituent, fused to one or more aromatic rings with or without a substituent member a 5-membered heterocycloalkyl group, a (C3-C30) cycloalkyl group having or not having a substituent, a (G3_(10)) cycloalkyl group condensed with one or more aromatic rings having or not having a substituent; , nitro, nr21r22, br23R24, PR2sR26, p(=〇)R27R28, 95136 201237137 R29R3〇R3iSi_, R32Z-, (C6_C30) aryl (C1-C30) alkyl with or without a substituent, with or without a (C2-C30) alkenyl group having a substituent, a (C2-C30) alkynyl group having or not having a substituent, Or each of them may be bonded to an adjacent substituent via a (C3-C30)alkylene group or a (C3-C30)alkylene group with or without a fused ring to form an alicyclic ring, a monocyclic ring or a polycyclic ring. a ring, or a monocyclic or polycyclic heteroaryl ring; ring A and ring B independently represent a (C5-C30) cycloalkyl group with or without a substituent, (C6-C30) aryl with or without a substituent a (C6-C30)heteroaryl group with or without a substituent; the core to R32 independently represents a (C-C30)alkyl group with or without a substituent, with or without a substituent (C6-C30 An aryl group, or a (C3-C30)heteroaryl group with or without a substituent; Z represents S or 0; W represents _(CR5lR52)m-, _(R51)C = C(R52)_, _N( R53)_, _S_, -0-, -Si(R54)(R55)---P(R56)-' -P(=0)(R5t)-, -C(=0)- or -B(R58 R41 to R43 and R51 to R58 are as defined for R! to R3; the heterocycloalkyl, heteroaryl or heteroaryl ring may contain a group selected from B, N, 0, S, P (= 0), one or more heteroatoms of Si and P; m represents an integer from 0 to 2; and a and b independently represent an integer from 0 to 4, and when a and b are greater than 2, 201237137 a b can be the same or different. 2. The organic electroluminescent compound according to claim 1, wherein the compound is selected from the group consisting of the following compounds: Among them, An to Ar3, Y, Ri, R2, r1q to r12, a and 5 are the same as those in Chemical Formula 1 of the first item of the patent application. 3. The organic electroluminescent compound according to claim 1, wherein An and An, L to R4, and R are further used. Substituents substituted with r12, I^ to R32, R41 to R43 and RS1 to R58 may be further substituted with one or more substituents selected from the group consisting of hydrazine, halogen, with or without dentate substitution (C1-C30)alkyl, (C6-C30) aryl, (C6-C30) aryl with or without (C6-C30) aryl substituent, with or without (C6-C30) (C6-C30) aryl group of aryl substituent, (C3-C30) heteroaryl group with or without (C6-C30) aryl substituent, (C3-C30) heteroaryl group, 5 to 7 members a heterocyclic alkyl group, a 5- to 7-membered heterocycloalkyl group fused to one or more aromatic rings, a (C3-C30) cycloalkyl group, (C3_C3〇) cycloalkane fused to one or more aromatic rings Base, NR6iR62 'BR63R64' PResRee 'P(=〇)R67R68 . R69R7〇R71Si- > R72Z- > R?3C(=0)-, R74C(=0)0-, (C2-C30)alkenyl, (C2-C30) alkynyl, cyano, carbazolyl, (C6-C30) aryl (C1_C30) alkyl, (cl_C3〇) alkyl (C6-C30) aryl, carboxyl, nitro and hydroxy; Can be linked to 95136 3 201237137 adjacent substituents to form a ring; R61 to R72 are independently represented ((n-C30) Or (C6-C30) aryl or (C3-C30)heteroaryl; Z represents S or hydrazine; and flank 73 and independently represents (C-C30) alkyl, (C1-C30) alkoxy, ( C6-C30) aryl or (C6_C3〇) aryloxy. 4. The organic electroluminescent compound according to claim 1, wherein the system is selected from the following structures. * Umbrella 95136 4 201237137 XT · =v.〇 An organic electroluminescent compound according to claim 1, wherein Ri and R2 are independently selected from the following structures: ••Η·*ρ An organic electric field illuminating device, which comprises the organic electroluminescent compound of any one of the above-mentioned claims. An organic electric field light-emitting device according to claim 6, wherein the first electrode, the second electrode, and one or more layers of the organic layer interposed between the first electrode and the second electrode Wherein the organic layer comprises one or more of the patent applications range i through 5; the organic electroluminescent compound and one or more of the 95136 5 201237137 dopants 化学 2 represented by Chemical Formula 2 The metals of Free Group 7, Group 8, Group 9, Group 10, Group 11, Group 13, Group 14, and Group 16, and the ligands Lm, Lm, and Lm are independently selected from the following structures : 6 95136 201237137 wherein R201 to R2D3 independently represent hydrogen, (C1-C30)alkyl with or without a halogen substituent, (C6-C30) aryl with or without (C1-C30)alkyl substituent, Or halogen; 1^. 4 to R219 independently represent hydrogen, (C1-C30)alkyl group with or without a substituent, (C1-C30) alkoxy group with or without a substituent, with or without a substituent (C3-C30) a cycloalkyl group, a (C2-C30) alkenyl group with or without a substituent, a (C6-C30) aryl group with or without a substituent, a mono- or di-(C1- with or without a substituent) C30) an alkylamino group, a mono- or di-(C6-C30) arylamino group with or without a substituent, SF5, a tri(C1-C30)alkyldecane group with or without a substituent, having Or a substituted (C1-C30)alkyl (C6-C30) arylalkylene group, a bis(C6-C30) sulphuryl group with or without a substituent, a cyano group or a halogen; And r223 independently represent a hydrogen atom, a hydrazine, a (cl__C3〇) alkyl group having or not having a halogen substituent, or a (C6-C30;) square group having or not having a (C1-C30) alkyl substituent, R224 and R225 independently represents hydrogen, an aryl group, a (C1-C30) alkyl group with or without a substituent, a (C6__C3〇) aryl group with or without a substituent, or a halogen; or Rm and R225 may or may not have The (C3-C12)alkylene group or the (C3_C12)alkylene group is bonded to form a halocyclic ring, or a monocyclic or polycyclic aromatic ring; or a (C-C30) alkane having or without a substituent a (C6_C3()) aryl group having, or having no substituent, a (C5_C30)heteroaryl group having no substituent, or a halogen; Rm to R229 independently representing hydrogen, deuterium, with or without a substituent (C1-C30)alkyl, (C6_C3〇)aryl with or without a substituent, 7 95136 201237137 or halogen, and R231 R232 ^73⁄43^^242 Q represents V, R235R23e or R239 R24. Wherein R23 丨 to R242 independently represent hydrogen, deuterium, (c-C30) alkyl group having or without a halogen substituent, (C1-C30) alkoxy group, _ 素, with or without a substituent ( C6-C30) aryl, cyano or (C5_C3〇)cycloalkyl with or without a substituent; or each of them may be bonded to an adjacent substituent via an alkyl or alkenyl group to form a spiro ring or a thick The ring may be attached to Rm or Rm via an alkyl or alkenyl group to form a saturated or unsaturated fused ring. 8. The organic electroluminescent device of claim 7, wherein the organic layer further comprises one or more amine compounds selected from the group consisting of an arylamine compound and an arylamine compound. Free organometallic, Group 2, and 4th cycles; One or more metals of a metal, a lanthanide metal, and a d_transition element. 9. In the organic electric field illuminating described in claim 7, the organic layer includes an electric field luminescent layer and a charge generating layer. The electric field illuminating device of the organic electric field emitting white light according to the seventh aspect of the patent patent, wherein the organic layer is filled with two ': layer or multilayer organic light field emitting blue light, red light or green light ·= 95136 8 201237137 IV. Designated representative map: There is no schema in this case (1) The representative representative map of this 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: Ri Ar^a 〆 (Ar3)b • R2 3 95136