TW201213504A - 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. Because the organic electroluminescent device using the organic electroluminescent compound as a hole transport material or a hole injection material exhibits good luminous efficiency and excellent lifetime properties, it is used to manufacture OLED devices having superior operating lifetimes and that consume less power due to improved power efficiency.

Description

201213504 VI. INSTRUCTIONS OF THE INVENTION: TECHNICAL FIELD This publication relates to novel organic electroluminescent compounds and organic electric field illuminating devices comprising the same, and more particularly to the present invention for use as a hole transmission A novel organic electroluminescent compound of a material or a hole injecting material and an organic electric field illuminating device using the same. [Prior Art] A liquid aa display (LCD) is a currently popular non-illuminated (n〇n-emissiVe) display device, which has low power consumption and light weight, has a complicated operating system and is unsatisfactory. The nature of this includes the fact that the current organic electric field illuminating device is quite suitable for the next generation of planar light-emitting devices and is being thoroughly studied for organic electric field illuminating devices. One of the advantages of the electric field illumination (EL) device as a self-luminous display device is that it provides a wide-angle field of view, a high contrast, and a fast response rate. In 1987, Ismen Kodak Yang Ghanu (10) exhibited the first organic EL device using a low molecular weight aromatic diamine heterocompound as a substance for forming an electroluminescent layer [Liu /. 51 913, 1987]. The organic electroluminescent device emits light by injecting a charge into an organic layer formed between the electron main electrode (cathode) and the hole injecting electrode (anode), and forms an electric L pair, which then decays and emits light. The device can be formed on a flexible transparent plate (such as a township), and compared with the electric panel or the inorganic electric field, the device can also be at a voltage of ig volts (v). Operating at low voltages and exhibiting relatively low power consumption and superior color. a — The organic material of the organic EL device can be roughly classified into an electric field luminescent material and a charge transport material. The electric field luminescent material is directly related to the electric field illuminating color two illuminating efficiency, and requires several characteristics such as high fluorescence quantum yield in the solid state, electron and electricity / the same mobility, low decomposition in vacuum deposition, uniform formation Film formation and stability of the film. Further, the hole injecting and transporting materials include ugly bronze (Cupc), NpB, TM, machiru (4,4,4"-gin(3-nonylphenylphenylamino)triphenylamine) and the like. The use of these materials in the hole injection or transport layer is problematic in terms of efficiency and operational life because thermal stress is generated between the anode and the hole injection layer when the organic EL device is driven at high current. Stress can significantly reduce the operational life of the device. Furthermore, since the organic material used in the hole injection layer has very high hole mobility, breaking the hole_electron charge balance' and thus reducing quantum yield ((4)(4)/ Ampere (4)). Amorphous compounds are known to provide good film stability and improve the operational life of organic EL devices. Glass transition temperature (6) can be a measure of amorphousness. MTDATA glass transition temperature is 76 ° C Therefore, it is not considered to have high degree of amorphism. These materials are unsatisfactory in organic lifetime [the operating life of the device and the luminous efficiency determined by the hole injection and transmission properties.] [Technical Problem] 4 201213504 In view of the above, the present invention is directed to the problems encountered in the related art, and the object of the present invention is to provide an organic electroluminescent compound having a skeleton which provides higher luminous efficiency than conventional hole injection or hole transport materials. And an organic electric field illuminating device using the novel organic electroluminescent compound as a hole injection layer or a hole transport layer. Technical Solution The present invention provides an organic electroluminescent compound represented by the following Chemical Formula 1, and a compound containing the same An organic electric field illuminating device. The organic electroluminescent compound of the present invention is included in a hole injection layer or a hole transport layer of the organic electric field illuminating device, thereby reducing the operating voltage of the device and increasing its luminous efficiency. In the present invention, the present invention provides an organic electroluminescent compound represented by the following Chemical Formula 1.

Wherein ring A and ring C are independently represented; R2)p χί^Ί 5 95328 201213504

Q ring B represents γ2; Χι and Χ2 independently represent CR>3 or Ν; 丫1 and Υ2 independently represent a chemical bond, -O-, -S-, ·cCRnRy-, -SKRuU- or -Ν^5)- ' Excluding examples in which both Yi and Y2 are chemical bonds;

Ri to R_3 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted ( C2-C30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted ( C6-C30) aryl (C1_C30) alkyl, substituted or unsubstituted (C1-C30)alkyldecyl, cyano, nitro or hydroxy' and when two or more of Ri or R2 , then they are linked to each other to form a cyclic structure; L represents a substituted or unsubstituted (C6_C30) extended aryl group, or a substituted or unsubstituted (C2-C30) heteroaryl group, and when L When there are two or more, then they are linked to each other to form a ring structure;

Ar! independently of Ar2 represents a substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (C2-C30)heteroaryl or

Y3 and I independently represent a chemical bond, -〇-, -S-, -C(R16R17)-, _Si(Rl8Rl9> or ·Ν(Ϊ120)-, excluding an example in which both Y3 and Y4 are chemical bonds; 6 95328 8 201213504

Ru to R2Q independently represent hydrogen H, substituted or unsubstituted (C1_C3G) silk, substituted or unsubstituted (c6_c3()) aryl, or substituted or unsubstituted (C2_C3〇) The aryl groups, or each of them may be substituted or substituted by a substituted or unsubstituted (C3_c3〇) stretching or substituted filament (C3_(3)) with or without a fused ring. a base chain to form an alicyclic ring and a monocyclic or polycyclic aromatic ring; m and η independently represent an integer of 0 to 4, and when 111 and 11 are integers of 2 or more, each core and L They may be the same or different from each other; Ρ represents an integer of 0 to 2, and when 卩 is 2, each oxime may be the same or different from each other; and the heterocycloalkyl, heteroaryl and heteroaryl include one or more A hetero atom selected from the group consisting of ruthenium, osmium, iridium, S, P (=〇), Si and ruthenium. [Embodiment] As used herein, the "alkyl" and other substituents containing the alkyl moiety include both straight and branched chains, and "cycloalkyl" includes monocyclic hydrocarbons as well as polycyclic hydrocarbons such as Substituted or unsubstituted adamantyl or substituted or unsubstituted (C7-C30)bicycloalkyl. As used herein, the term ", aryl" means organic after removal of a hydrogen atom from an aromatic hydrocarbon. A group, and including 4 to 7 members, especially a 5- or 6-membered monocyclic or fused ring, and more includes a plurality of structures of aryl groups linked by a single bond. Specific examples thereof include, but are not limited to, phenyl, naphthyl, biphenyl, terphenyl, fluorenyl, fluorenyl, decyl, phenanthryl, triphenylenyl, fluorenyl , peryienyi, chrysenyl, naphthacenyl, fluoranthenyl, and the like. Naphthyl includes 1·naphthyl and 2-naphthyl, and fluorenyl 7 95328 201213504 includes i-fluorenyl, 2-fluorenyl and 9-fluorenyl, and phenanthryl includes r phenanthryl, 2-phenionyl, l phenanthrene The group, 4-phenanthryl and 9-phenanthryl, the fused tetraphenyl group includes r slightly tetraphenyl, anthracenyltetraphenyl, 9-fused tetraphenyl. The records include Buxian, 2_youji and 4_youji, and biphenyl includes 2-phenylene (2_biphenyl), 3-formyl and 4-phenyl, and triphenyl including p-terphenyl-3 · base, p-terphenylene _3_yl, p-tertiary, m-triphenyl-4-yl, m-triphenyl-3-yl and m-triphenyl-2-yl, And the first group includes a 1-position, a 2-indenyl group, a 3_diyl group, a group and a 9-diyl group. As used herein, "heteroaryl" means a radical containing as an aromatic ring skeleton atom selected from the group consisting of ^4 small (four) broad (four) to form a group of ^f4 heteroatoms' and as a remaining aromatic ring skeleton atom. The aryl group may be a 5- or 6-membered monocyclic heteroaryl group or may be partially saturated with one or more of the abbreviated rings and may be partially saturated. In the present invention, "heteroaryl" , comprising a structure in which one or more heteroaryl groups are bonded by a single bond, and the aromatic ring includes a divalent aryl group, wherein the hetero atom in the ring may be oxidized or quaternized to form a shape such as N - an oxide or 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, an imidazolyl group, a pyridyl group, a decyl group, a stilbene group, a snail group, and a fluorenyl group. , ^ sitin, oxime, trisyl, tetradecyl, tris-s, sulphonyl" bite base, sulfhydryl group, base group, polycyclic heteroaryl, such as benzene And furan, benzothienyl, dibenzofuranyl, dibenzothiophenyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, stupid And oxazolyl, isodecyl, decyl, oxazolyl, benzothiazolyl, quinolyl, isoquinolinyl, porphyrin, quinazolinyl, quinoxalinyl, carbazole Benzodinyl, benzodiazepine* (benz〇di〇x〇lyl), 8 95328 201213504 σΥσ定基, phenanthrolinyl, α non-anthraquinone, morphine D thiol, brown cultivating a base or the like, an N-oxide thereof (such as pyridyl N-oxide, quinolyl N-oxide), a quaternary salt thereof, etc. The pyrrolyl group includes a 1-pyrrolyl group, a 2-pyrrolyl group and a 3-pyrrolyl group; Pyridyl includes 2-pyridyl 3-pyridyl and 4-pyridyl; 吲11-based group includes 1-indenyl, 2-indolyl, 3-indenyl, 4-indolyl, 5-nonyl, 6-fluorenyl And 7-fluorenyl; isodecyl includes 1-isoindenyl, 2-isoindolyl, 3-isoindolyl, 4-isoindenyl, 5-isodecyl, 6-iso Sulfhydryl and 7-isodecyl; furyl includes 2-furyl and 3-furyl; benzofuranyl includes 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl and 7-benzofuranyl; isobenzofuranyl includes 1-isobenzofuranyl, 3-isobenzofuranyl, 4-isobenzofuranyl , 5-isobenzofuranyl, 6-isobenzofuranyl and 7-isobenzopyranyl; fluorinyl includes 3-mercapto, 4-mercapto, 5-quinone, 6-啥琳基, 7-喧琳基 and 8-喧喧基; isoindolinyl includes 1-isoindolinyl, 3-isoquinolinyl, 4-isoquinolinyl, 5-isoquinolinyl, 6 -isoquinolyl, 7-isoquinolinyl and 8-isoquinolinyl; quinoxalinyl includes 2-quinoxalinyl, 5-anthracene and 6-indole; Base includes 1-π-carbyl group, ·2-π-carbyl group, 3-flavor base, 4-σ-carbyl and pendant; the morphine includes 1--bite, 2-cyridinyl, 3-cyridinyl, 4-cyridinyl, 6-cyridinyl, 7-pyridinyl, 8-cyridinyl, 9-cyridinyl and 10-cyridinyl; acridinyl includes 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridine And 9-acridinyl; morpholinyl includes 1,7-morpholin-2-yl, 1,7-morpholin-3-yl, 1,7-morpholin-4-yl, 1,7-morphyl Porphyrin-5-yl, 1,7-morpholin-6-yl, 1,7-morpholin-8-yl, 1,7-morpholin-9-yl, 1,7-morphine "-ΙΟ- , 1,8-morphin-2-yl, 1,8-morphol-3-yl, 1,8-morphol-4-yl, 9 95328 201213504 Μ-morpholin-5-yl, 1,8 -Porphyrin-6-yl, M-phenanthroline-7-yl, M-phenanthroline, 1,8-morpholin-10-yl, anthracene, 9-morpholin-2-yl, anthracene, 9-phenoline _3 base, H morpholin-4-yl, i, 9- phenanthroline _5·yl, hydrazine, 9- phenanthroline -6-yl, i, 9- phenanthroline -7-yl, 1,9-morphine Porphyrin-8-yl, 1,9-morpholine·10-yl, phenanthroline-2-yl, ^(7) phenanthroline-3-yl, 1,1 〇 phenanthroline-4-yl, u〇-phenoline _5 base, 2,9 phenanthroline-indenyl, 2"-lin-3-yl, 2,9-morphine-based, 2,9-morpholin-5-yl, 2,9-morphine-6- Base, 2,9-morpholin-7-yl, 2,9-morpholine , 2,9-morpholin-10-yl, 2,8-morpholin-1-yl, 2,8-morpholin-3-yl, 2,8-morpholin-4-yl, 2,8-morphine Porphyrin-5-yl, 2,8-morpholin-6-yl, 2,8-morpholin-7-yl, 2,8-morpholin-9-yl, 2,8-morpholin-10-yl, 2,7-Promaline-1-yl, 2,7-morpholin-3-yl, 2,7-morpholin-4-yl, 2,7-morpholin-5-yl, 2,7-morpholine -6-yl, 2,7-morpholin-8-yl, 2,7-oxalinyl and 2,7-morpholin-10-yl; morphinyl includes _ _ _ _ _ _ _ _ _ _啡 ; 包括 包括 包括 ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; ; Sulfhydryl, 2_ morphine, etc., 3-morphine, cultivating, 4-morphine, and 1 〇 噚 噚 噚; oxazolyl including 2-carbazolyl, 4-carbazole And 5-oxazolyl; oxazolyl and the like have a 2-oxadiazolyl group and a 5-oxadiazide group; a τ-»-fluorenyl group includes a 3-fluorenyl group; and a dibenzo-anthracene group includes a dibenzoate group.吱 基, 2-dibenzo. a fluoromethyl group, a 3-dibenzo-t-butyl group and a 4-dibenzofuranyl group; and a dibenzothienyl group including a 1-dibenzothiophenyl group, a 2-dibenzothiophenyl group, a 3-dibenzothiophene group. And 4-dibenzothiophenyl. As used herein, the term "(C1-C30)alkyl" includes (C1-C20)alkyl or (C1-C10)alkyl, and the term "(C6"C30)aryl" includes (C6-C20 An aryl or (C6-C12) aryl group. The term "(C2-C30)heteroaryl" includes (C2-C20)heteroaryl or (C2-C12)heteroaryl, and the term "(C3-C30)cycloalkyl,•Package 10 95328 8 201213504 (C3-C20)cycloalkyl or (C3-C7)cycloalkyl. The term "(C2-C30)alkenyl or alkynyl" includes (C2-C20)alkenyl or alkynyl, or (C2-C10) Alkenyl or alkynyl. The term "substituted (having a substituent)" in the term "substituted or unsubstituted (or with or without a substituent)" as used herein means that the unsubstituted substituent is further substituted with a substituent. Each of the substituents represented by r2, r3, L, Ar!, Ar2 and Ri1 to R2〇 may be further substituted with one or more substituents selected from the group consisting of hydrazine, halogen, dentate substituted or unsubstituted. (C1-C30)alkyl, (C6-C30)aryl, (C6-C30)aryl substituted or unsubstituted (C2-C30)heteroaryl, 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl, (C3-C30) cycloalkyl fused to one or more aromatic rings, (C6_C30) cycloalkyl fused to one or more aromatic rings, (C2_c3 〇) alkenyl, (C2-C30) alkynyl,

, cyano, carbazolyl, (C6-C30) aryl (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, -NR23R24, -PR25R26, _SiR27R28R29, nitro and

-0R21, -SR hydroxy, and γη and γ12 independently represent a chemical bond, _c, -〇·, -s· or -n(r33)_ 'excluding an example in which both Yll and Υΐ2 are chemical bonds; and R21 to R29 And independently from r31 to r33, (C1_C30) alkyl group, (C6-C30) aryl group, (C2-C30) heteroaryl group, or (C3_C3〇) cycloalkyl group.

In Chemical Formula 1, Ring A

Condensed to, π-ring, and 95328 11 201213504 Table 6 aromatic rings or 6 nitrogen-containing aromatics

It is fused to ring A and represents a 5- or 6-member and represents a 6-member aromatic ring or

It is fused to the ring B. Further, the chemical formula 1 is not limited thereto. 6-membered nitrogen-containing heteroaromatic ring

(R2)p

(R2)p 12 95328 8 201213504

Wherein 'R2, Rh to R15 and P are as defined in the formula i. Specifically, L represents (C6-C30) an extended aryl group; Ari and independently represent a (C6-C30) aryl group, a (C2-C30) heteroaryl group, or

Y3 and Y4 are independent of N(R2〇)-, r16, ri7 and r2〇 independently represent (cK3〇)alkyl, (C6_C3〇)aryl or (C2-C30)heteroaryl, or R16 and Rl7 Substituted or unsubstituted (C3-C30) alkylene group or substituted or unsubstituted (C3-C30) extended alkenyl chain 'with or without a fused ring to form an alicyclic group 13 95328 201213504 Ring or monocyclic or polycyclic aromatic ring; R1 represents hydrogen, (c6 c3〇) aryl or (C2-C30)heteroaryl, or may be linked to an adjacent substituent via hydrazine, \^ or 1Un; a aryl group of L, an alkyl group of an Aq and Αι*2, an aryl or heteroaryl group, an aryl group of R1 or a heterocyclic group of Rl6' Rl7, R2, substituted by one or more substituents, the substitution Further, the aryl group may be further substituted, halogen, or substituted (C6_C3〇) aryl, (Cl C3〇), deuterated 4-halo (C6-C30) aryl substituted or unsubstituted ( C2_c3〇) heteroaryl, &heterocycloalkyl, 5,5 to 7-yl, fused to one or more aromatic rings, β "carbocarb and torn 23R24

Yn and Yu independently represent -(^RmR32)-, 七_, _s_ or · and r24, R31, R32 and r33 independently represent (Cl_C3〇) aryl or (C2_C30)heteroaryl. K6 'C3 〇) The organic electroluminescent compound of the present invention can be exemplified below, but is not intended to limit the scope of the present invention. Listing 95328 14 201213504

95328 15 201213504

16 95328 8 201213504

〇xr° ^

34

36

17 95328

S 201213504

18 95328 8 201213504

19 95328

s 201213504

201213504

21 95328 s 201213504

N

201213504

23 95328 201213504

24 95328 8 201213504

25 95328 201213504

The organic electroluminescent compound of the present invention can be produced, for example, according to the following Scheme 1, but it is not limited thereto. [Scheme 1] 26 95328 8 201213504

Among them, the definitions of eight, six, €, 111, 1^, human 1*1, human 犷2, 111 and 11 are the same as defined in Chemical Formula 1. Further, the present invention provides an organic electric field light-emitting device in which the organic electroluminescent compound of the present invention is used as a hole injecting material or a hole transporting material. When the organic electroluminescent compound represented by Chemical Formula 1 of the present invention is used for a hole injection layer or a hole transport layer, it can be used to manufacture an OLED device which consumes less power due to improvement in power efficiency. The organic electric field light-emitting device of the present invention comprises 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 Organic electric field luminescent compound. Further, the organic layer may include one or more electroluminescent layers in addition to one or more organic electroluminescent compounds represented by Chemical Formula 1. The electroluminescent layer may further comprise one or more dopants or moieties. The dopant or host to be used in the organic electroluminescence device of the present invention is not particularly limited, but may be selected from the following Chemical Formulas 2 to 6. 27 95328 201213504 wherein Μ1 represents Ir, Pt, Pd or Os; the ligands L101, L102 and L103 are independently selected from the following structures:

Κ·2〇ι to R2G3 independently represent hydrogen, aryl, halogen-substituted or unsubstituted (C1-C30)alkyl, substituted by (C1-C30)alkyl or unsubstituted (C6-C30) aryl Or a halogen; 28 95328 201213504 R204 to 219, 219 independently represent a hydrogen, a hatched, substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, Substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted Substituted mono or di-(C1-C30)alkylamino, substituted or unsubstituted mono- or di-(C6-C30) arylamino, SF5, substituted or unsubstituted III (C1 -C30)alkylalkylalkyl, substituted or unsubstituted bis(C1-C30)alkyl(C6-C30)aryldecyl, substituted or unsubstituted bis(C6-C30) aryl Shixiyuan a group, a cyano group or a halogen; R22〇 to R223 independently represent hydrogen, deuterium, halogen-substituted or unsubstituted (C1-C30) alkyl group, or substituted or unsubstituted with (C1-C30)alkyl ( C6-C30) aryl; 'R224 and R225 independently represent hydrogen, gas, substituted or Substituted (C1-C30)alkyl, halogen-substituted or unsubstituted (C6-C30) aryl, or halogen ' or R224 and R225 may be substituted or unsubstituted via with or without a fused ring a (C3-C12)alkylene group or a substituted or unsubstituted (C3-C12)alkylene group attached to an adjacent substituent to form an alicyclic ring or a monocyclic or polycyclic aromatic ring; R226 And a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted (C2-C30) heteroaryl group or a halogen; To R229 independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6_C30) aryl, or halogen; and 29 95328 201213504 Q represents

Wherein R231 to R242 independently represent argon, hydrazine, halogen-substituted or unsubstituted (C1-C30) alkyl, (C1-C30) alkoxy, halogen, substituted or unsubstituted (C6- C30) an aryl group, a cyano group, a substituted or unsubstituted (C3-C30) cycloalkyl group, or they may be bonded to an adjacent substituent via an alkyl or alkenyl group to form a spiro ring or a fused ring. Alternatively, it may be linked to R2〇7 or 208 via an alkyl or alkenyl group to form a saturated or unsaturated fused ring. [Chemical Formula 3]

Wherein Z represents -〇-, -S-, -C(R41R42)_, -Si(R43R44)- or -N(R45)_;

Ring E represents Y24; Υ21 and Υ22 independently represent CH or Ν; Υ23 and Υ24 independently represent a chemical bond, -Ο-, -S-, -C(R41R42)_, -Si(R43R44)-, or -N(R45 )-'Exclude an example in which both Y23 and Y24 are chemical bonds;

Rn and R.sup.32 independently represent hydrogen, deuterium, dentate, substituted or unsubstituted (C1-C30) leumino, substituted or unsubstituted (C6-C30) aryl, 95328 30 201213504 substituted Or unsubstituted (C2-C30)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted 5 to 7-membered heterocycloalkyl, substituted or Unsubstituted (C6_C30) aryl (cl_c3 fluorene) alkyl, substituted or unsubstituted (C1-C30) alkyl decyl, substituted or unsubstituted (C6-C30) aryl sulphur , substituted or unsubstituted (cl C3〇) alkyl (C6-C30) arylalkyl, cyano, nitro or hydroxy, or they may be substituted or unsubstituted with or without a fused ring Substituting (C3 c3〇) alkyl or substituted or unsubstituted (C3_C3〇) an alkenyl group with an adjacent substituent to form an alicyclic ring and a monocyclic or polycyclic aromatic ring; IUi To R45 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C3 indenyl) aryl, substituted or unsubstituted ( C2_C30) heteroaryl, substituted or not a substituted 5- to 7-membered heterocycloalkyl group, or a substituted or unsubstituted (C3-C30) cycloalkyl group with or without a substituent, or each of which may be bonded to an adjacent substituent chain The knots form a ring; r and q independently represent an integer of 〇 to 4, and when ^ and ^ are integers of 2 or more, each ruler and ruler 32 may be the same or different from each other, or each of them may be Linking with adjacent substituents to form a ring; the heterocyclic alkyl group and heteroaryl group include one or more selected from the group consisting of B, N, 〇, S, P(=〇), Si and P atom. (Cz-L2) a-M [Chemical Formula 5]

(Cz)b_L2_M 95328 31 201213504 wherein Cz is selected from the following structures,

Ring ^ mail 6_c Hua _, version (3) chest ring or (C2_C30) R51 and R53 independently represent hydrogen, hydrazine, _ 素, substituted or unsubstituted (C1_C3 〇) alkyl, substituted or unsubstituted ( C6-C30) aryl, substituted or unsubstituted (C2_C3〇)heteroaryl, substituted or unsubstituted 5-7 to 7-membered heterocyclic, with one or more substituted or unsubstituted a substituted (C3-C30) cycloalkyl group which is substituted or unsubstituted (10) refers to an aryl group, which is fused to one or more substituted or unsubstituted aromatic rings. a substituted or unsubstituted (C3 C3 indenyl) cycloalkyl group, a (6) fluorene ring fused to one or a substituted or unsubstituted aromatic ring, substituted or unsubstituted (C6_C3〇) aryl (cl_C3〇)alkyl, cyano, deterministic, thiol, -BR61R62, _Pr63r64, Ρ(=〇)]ΐ65ΐΐ66, R67R68R69Si-, -nr70r71 or _丫尺72, or they may Substituted (C3_C30) alkyl or substituted or unsubstituted (C3_C30) extended alkenyl group with or without a fused ring to form an alicyclic ring with an adjacent substituent group Single ring The polycyclic aromatic ring, and the carbon atom of the formed alicyclic oxime and the monocyclic or polycyclic aromatic ring are substituted by one or more hetero atoms selected from the group consisting of ruthenium, oxygen and sulfur, ]^2 and R53 may be the same or different from each other; 32 95328 8 201213504 y denotes 〇 or s;

Rw to R72 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6_C3〇) aryl, substituted or unsubstituted (C2 -C30) a heteroaryl, substituted or unsubstituted 5- to 7-membered heterocycloalkyl group substituted with one or more substituted or unsubstituted (C3-C30) cycloalkyl groups Or unsubstituted (C6_c30) aryl, 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C3_C30) ring fused to one or more substituted or unsubstituted aromatic rings a (C3_C3〇)cyclod, fused or unsubstituted (C6-C30) aryl (Ci_C30) alkyl, cyano group fused to one or more substituted or unsubstituted aromatic rings , nitro or hydroxy; L2 represents a chemical bond, a substituted or unsubstituted (C6_C30) aryl group, or a substituted or unsubstituted (C2-C30)heteroaryl group; Μ represents substituted or unsubstituted ( C6-C30) aryl, or substituted or unsubstituted (C2-C30)heteroaryl; a, b, c and d independently represent an integer from 0 to 4. [Chemical Formula 6]

among them,

Ai to A19 independently represent CR81 or N; 33 95328 201213504 X Table -C(R82R83)-, -N(R84)·, _s-, -Ο-, _Si(R85)(R86)_, -P(R87 )-, -P(=〇)(r88)- or _B(R89)_ ;

An i represents a substituted or unsubstituted (C6 C4〇;) extended aryl group or a substituted or unsubstituted (C2-C40) heteroaryl group, excluding e is hydrazine, and A. To Ai9 is also an example of CR81; RS1 to R89 independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C3〇) aryl a substituted or unsubstituted (C6_C30) aryl group, a substituted or unsubstituted (C2_C30) heteroaryl group fused to one or more substituted or unsubstituted (C3_C3〇)cycloalkyl groups, Substituted or unsubstituted 5 to, heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused to one or more substituted or unsubstituted aromatic rings, substituted or unsubstituted 2 (C3_C3〇)cycloalkyl, (C3_C3〇)cycloalkyl, cyano, di-methylmethyl, _NR9IR92, _br93r94, ΡΚ95ΐΐ96, -P fused to one or more substituted or unsubstituted aromatic rings (=〇)R97R98, R99R1〇〇Rl〇lSi...ri〇2y2i...Ri〇3C(=〇),

Ri〇4C(=o)〇-, substituted or unsubstituted (C6 C3〇)aryl pc%) alkyl, substituted or unsubstituted (C2_C3〇)alkenyl, substituted or unsubstituted (C2-C30)alkynyl, enyl, nitro or thiol, or they may be substituted or unsubstituted (C3-C30) alkyl or substituted with or without a fused ring Substituted (C3_C3〇)alkylene groups are bonded to adjacent substituents to form an alicyclic ring and a monocyclic or polycyclic aromatic ring;

Rw to R98 independently represent substituted or unsubstituted alkyl, substituted or unsubstituted (C6_C3〇) aryl, or substituted or unsubstituted (C2-C30)heteroaryl; 95328 8 34 201213504 R" to H1G1 independently represents substituted or unsubstituted (ci_C30) alkyl or substituted or unsubstituted (C6_C3〇) aryl; Y21 represents S or hydrazine;

Rl〇2 represents a substituted or unsubstituted (C1_C30) alkyl group or a substituted or unsubstituted (C6-C30) aryl group;

Ri〇3 represents a substituted or unsubstituted (C1_C3〇)alkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted (C6-C30) aryl group or a Substituted or unsubstituted (C6_C3〇) aryloxy;

Run represents a substituted or unsubstituted (cl_C3〇)alkyl group, a substituted or unsubstituted (C1-C30) alkoxy group, a substituted or unsubstituted (C6-C30) aryl group, or a substituted group. Or unsubstituted (c6_C3〇) aryloxy; e represents an integer of 2; the heterocycloalkyl, heteroaryl and heteroaryl include one or more selected from B, N, 0, S a hetero atom of the group consisting of P(=〇), si and p; the term described in Chemical Formulas 2 to 6, substituted or unsubstituted, the term, substituted 'is an unsubstituted substituent further Substituted by one or more substituents. The substituent represents one or more substituents selected from the same substituents as those represented by Chemical Formula 1. Specifically, the following compounds can be used in Chemical Formulas 2 to 6. 35 95328 201213504

36 95328 8 201213504

D-37 D-38 37

95328 201213504

38 95328 8 201213504

39 95328 201213504

40 95328 8 201213504

41 95328 201213504

42 95328 8 201213504

The organic electroluminescent device of the present invention comprising the organic electroluminescent compound of Chemical Formula 1 may further comprise one or more compounds selected from the group consisting of arylamine compounds and styryiamjne compounds, and the arylamine compound Specific examples of the styrylamine compound are listed in paragraphs <212> to &lt;224&gt; of Korean Patent Application No. 10-2008-0060393, but are not limited thereto. In the organic electric field light-emitting device of the present invention, the organic layer may further comprise, in addition to the organic electroluminescent compound of Chemical Formula 1, a bubble or a plurality of metals selected from the group consisting of: i-th, second, The compound of the first cycle and the first transition metal, the aged metal and the &amp; transition element. The organic layer may comprise an electric field emitting device. The organic electric field illuminating device capable of realizing a pixel structure having an independent illuminating mode, wherein the surface electric field displacing comprises the organic electroluminescent compound represented by the chemical formula 1 of the present invention as 95328 43 201213504 a pixel, and one or more metal compounds comprising one or more metal compounds selected from the group consisting of Ir, Pt, Pd, Rh, Re, 〇s, Tl, Pb, Bi, In, Sn, Sb, Te, Au, and Ag Pixels, which are simultaneously parallel patterned. Further, the organic layer may include, in addition to the organic electroluminescent compound of the formula i, one or more layers of an organic electroluminescent layer that simultaneously emits blue, green or red light to produce an organic electric field emitting device that emits white light. The series of compounds which emit blue light, green light or red light are shown in the compounds described in Korean Patent Application No. 10-2008-0123276, No. 1 〇 〇〇 8-0107606, or No. 10-2008-0118428. But it is not limited to this. In the organic electric field light-emitting device of the present invention, a layer (hereinafter referred to as "surface layer") may be selected from a layer of a chalcene genide layer, a layer of a metal dentate layer and a metal oxide layer. On the inner surface of one or both electrodes of the electrode pair. 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,

Further, a metal halide layer or a metal oxide layer may be disposed on the cathode surface of the electric field luminescent medium layer. Thereby achieving operational stability. The chalcogen compound may be, for example, Si〇x (l &lt;&lt; xs 2), Α1〇χ (κ i 5), si〇N, siA1〇N, or the like. The metal halide may be, for example, LiF, CaF2, rare earth metal fluoride or the like. The metal oxide may be, for example, Cs2〇, Li2〇, Mg〇,

SrO, Ba〇, CaO, etc. In the organic electroluminescence device of the present invention, a mixed region of electron-negative σ- and reductive dopants or a mixed region of a hole-transporting compound and a bismuth-producing dopant may be disposed in the above-mentioned manner. The electrode pairs to 44 95328 8 201213504 less on the surface. In this case, since the electron transporting compound is reduced to an anion, it becomes easier to inject and transport electrons from the mixed region to the electroluminescent medium layer. In addition, since the hole-passing compound is oxidized to a cation, it becomes easier for the hole to be injected from the mixing region and transmitted to the electric field. Preferred oxidizing dopants include various Lewis acids and acceptor (iv) ruthenium (10) compounds. Preferred reducing dopants include metal, metal-based compounds, soils, rare earth metals, and mixtures thereof. Further, an electric field emitting light emitting white light having two or more electric field light-emitting layers can be produced by using a reductive doping layer as a charge generating layer. Advantageous Effects According to the present invention, an organic electric field luminescent compound can be used as a hole-passing material or an electric-injection material, which can produce a good organic light-emitting device with good luminous efficiency and a different material lifetime f. This compound can be used to fabricate LED devices with extremely high operating lifetimes and less power consumption due to improved power efficiency. The best mode of the vehicle, ♦ the invention will further exemplify the invention, the electric field filament compound, the preparation branch thereof, and the electric field luminescence product. It is provided for illustrative purposes and is not intended to limit the scope of the invention. [Preparation Example 1] Preparation of Compound 1 A 95328 45 201213504

Preparation of Compound 1-1 30 g (g) of 2-iodobenzene (120.4 mmol), 26 g of 4-bromophenylboronic acid (132.5 mmol), 6.9 g of Pd(PPh3)4 (6.02 mmol), and 150 ml (mL) of 2M Na2C〇3 was added to 500 mL of toluene, and the mixture was heated at 10 °C. After 4 hours, the mixture was cooled at room temperature and extracted with ethyl acetate. After washing with distilled water, the water gas was removed with MgS04, distilled under reduced pressure, and separated through a column to obtain 28 g of compound l-l (i.68 mmol, 83.33%). Preparation of Compound 1-2 28 g of Compound 1-1 (10.68 mmol) was added to 300 mL of triethyl phosphite, and stirred at 150 ° C for 6 hours. After cooling at room temperature, the mixture was subjected to distillation under reduced pressure and extracted with ethyl acetate. The resulting material was washed with distilled water. After the water vapor was removed by MgS〇4, the pressure was reduced and the mixture was separated by a column to obtain llg of compound Hi4.4.6911111101, 44.38%). Preparation of Compound 1-3 30 g of compound 1-2 (101.29 mmol), 41.3 g of iodine iodide (202.59 mmol), 9.6 g of Cul (50.64 mmol), 82.5 g Cs2C03 46 95328 8 201213504 (253.2mmol), and 600mL of benzene mixed, and heat at 50〇C. 6.8 mL of ethylenediamine (101.29 mmol) was added to the mixture, and the mixture was stirred under reflux. After 14 hours, the mixture was allowed to cool at room temperature, and distilled water was added. The resulting mixture was extracted with ethyl acetate. After removing the water vapor with MgS04, distillation under reduced pressure was carried out, and after separation by a column, 32 g of Compound 1-3 (85.96 mmol, 84.86%) was obtained. Preparation of Compounds 1-4 32 g of Compound 1-3 (85.96 mmol) were dissolved in 300 mL of THF, and 37.8 mL of n-butyllithium (94.55 mmol, dissolved in 2.5 M hexane) was slowly added at -78 °C. Add the mixture. After 1 hour, 12.4 mL of triacetic acid borate (111.7 mmol) was added to the mixture. After the mixture was stirred at room temperature for 12 hours, distilled water was added to the mixture in the mixture, and the mixture was extracted with ethyl acetate. After removing the water vapor with MgS04, distillation under reduced pressure was carried out, and after separation by a column, 20 g of Compound 1-4 (59.31 mmol, 69.00%) was obtained. Preparation of compound 1-5

20 g of compound 1_4 (59.31 mmol), 14.3 g of 1-bromo-2-nitrobenzene (71.17 mmol), 2.7 g of Pd(PPh3)4 (2.37 mmol), and 75 mL of 2M

Na2C〇3, 300 mL of toluene was mixed with 70 mL of ethanol and scrambled at reflux. After 5 hours, the mixture was allowed to cool at room temperature, and distilled water was added to the mixture. The mixture was extracted with ethyl acetate. After removing the water gas with MgS04, it was subjected to vacuum distillation to separate by column to obtain 20 g of Compound 1_5 (48.25 mmol, 81.36%). Preparation of Compound 1-6 After 200 mL of triethyl phosphite was added to 2 g of compound 1_5 47 95328 201213504 (48.25 mmol), the mixture was stirred at 150 ° C for 6 hours and cooled at room temperature. After the distillation under reduced pressure, the mixture was extracted with ethyl acetate, and the obtained material was washed with distilled water. After removing the water gas with MgS04, distillation under reduced pressure was carried out through a column to give 7 g of compound 1-6 (18.30 mmol, 37.93%). Preparation of Compound 1 7 g of Compound 1-6 (18.30 mmol), ll.9 g of 4-bromo-N,N-diphenylaniline (36.60 mmol), 1.7 g of CuI (9.15 mmol), and 11.6 g of K3PO4 ( 54.90 mmol), and 100 mL of toluene were mixed and heated at 50 °C. 1.2 mL of ethylenediamine (18.30 mmol) was added to the mixture, and the mixture was stirred at reflux. After 14 hours, the mixture was allowed to cool at room temperature, and distilled water was added to the mixture. The mixture was extracted with ethyl acetate. After removing water vapor with MgS04, distillation under reduced pressure was carried out through a column to obtain 8 g of Compound 1 (17.44 mmol, 95.33%). MS/FAB was found to be 576 and the calculated value was 575.70. [Preparation Example 2] Preparation of Compound 15

Preparation of Compound 2-1 15 g of 1-bromo-2-ylidenebenzene (0 074 m〇i) was added to "liters of (1) 2 neck RBF and then mixed with d23g of 9,9-dimethyl-9H- Indole-2-ylboronic acid (0.096 mol), 4.2 g of Pd(PPh3)4 (〇.〇〇3m〇l), iiimL of Na2CO3 (2M), and 111 mL of ethanol. After 200 mL of toluene was added to the mixture 48 95328 8 201213504, the mixture was heated at 120 ° C for 3 hours and stirred. After the reaction was completed, the obtained material was washed with distilled water and extracted with ethyl acetate. The water of the organic layer was removed with Mg s 〇 4 and the solvent was removed by a rotary evaporator, and then purified by column chromatography to obtain 22 g of Compound 2-1 (95%). Preparation of Compound 2-2 After adding 24 g of the compound 2-l (0.076 mol) to the 2-neck RBF of il, 200 mL of triethyl phosphite, and 2 〇〇mLi 1 &gt; 2-dichlorobenzene were added to the mixture. , at MOt: heated for 12 hours and stirred. After the reaction is completed, the solvent is distilled. The resulting material was washed with distilled water and extracted with ethyl acetate. After removing the water vapor of the organic layer with MgSCU, and removing the solvent by column chromatography to purify by rotary evaporator, 7 g of compound 2-2 (33%) was obtained. Preparation of compound 15 7 g of compound 2-2 (18.30 mm 〇l), I3.7 g of N-(4-phenylene)-N-phenylnaphthalen-2-amine (N-(4-diphenyl) _N-Phenylnaphthalene-2-amine (36.60 mmol), 1.7 g of CuI (9.15 mm 〇l), 11.6 g of K3P〇4 (54.90 mmol), and 100 mL of hydrazine were mixed and heated at 5 (rC). 1 2 mL of ethylenediamine (18 3 mmol) was added to the mixture, and the mixture was stirred under reflux. After 14 hours, the mixture was cooled at room temperature, and distilled water was added to the mixture. After removing the water vapor with MgS〇4, it was subjected to distillation under reduced pressure and separated by a column to obtain 8 g of Compound 15 (17.44 mmol, 95.33%). MS/FAB found 577, calculated 576.73. [Preparation 3] Compound 22 Preparation 49 95328 201213504

Preparation of compound 3-1 7 g of 2-bromo-9H-carbazole (i8 30 mm〇i), 13 7 g of n_(4_(9H-mouth bayonet _9_yl)phenyl) ice phenyl Aniline (36 6 〇 mm 〇 1) 1 7 g of CuI (9.15 mm 〇 1), U. 6 g of Κ 3 ρ 〇 4 (54 9 〇 mm 〇 1), and 100 mL of hydrazine mixed 'and added at 5 (TC heating. After 12 mL of ethylenediamine (i 8.30 mmol), the mixture was stirred at reflux. After 14 hours, the mixture was cooled at room temperature, and water was added to the mixture. The mixture was extracted with ethyl acetate. After the water vapor was distilled under reduced pressure and separated through a column to obtain 8 g of compound 3-1 (17.44 mmol, 95.33%). Preparation of compound 3-2 12 g of compound 3-l (37.42 mmol), 7.5 g of 2-( Methylthio)phenyl phthalic acid (44.69 mmol), 2.15 g of Pd(PPh3)4 (1.6 mmol), 45 mL of 2M aqueous Na2CO3, and 200 mL of THF were mixed and stirred at reflux. It was cooled at room temperature and extracted with ethyl acetate. The obtained material was washed with distilled water. After removing water vapor with MgS 4 , it was evaporated under reduced pressure and separated by a column to obtain 10 g of compound 3-2 (27.36 mmol, 73.47%). ) 50 95328 8 201213504 Preparation of compound 3-3 10 g of compound 3-2 (27.36 mmol) was added to 100 mL of acetic acid' and 2.65 mL of H 2 〇 2 (3 〇. 〇 9 mmol, 35%) was slowly added to the mixture. The mixture was stirred at room temperature for 12 hours, and acetic acid was distilled under reduced pressure. The obtained material was extracted with dioxane and neutralized with NaHC03 solution. After removing water vapor with MgS04, distillation under reduced pressure was carried out to obtain 10 g of compound 3-3 (26.21 Mmol, 95.79%) Preparation of Compound 22 10 g of compound 3-3 (26.21 mmol) was mixed with 70 mL of trifluoromethane-retinoic acid and mixed at 100°. Cooled and added to a mixture of 100 mL (β ratio bite: steamed water = 1:5). The mixture was stirred at reflux and cooled at room temperature. The solid obtained was filtered under reduced pressure. Compound 22 (17.16 mmol, 65.47%). MS/FAB found 682.

Preparation of Compound 4-1 1 g of dibenzo[b,d]thiophen-4-ylboronic acid (43.84 mmol), 8.85 g of nitrobenzene bromide (43.84 mmol), 70 mL of 2M Na2CO3 solution, 200 mL of Mix with 7 〇 niL of ethanol and stir at reflux. After 5 hours, 51 95328 201213504 the mixture was allowed to cool at room temperature and the mixture was extracted with ethyl acetate. The resulting material was washed with distilled water. After removing water vapor with MgS04 and performing distillation under reduced pressure, 10 g of Compound 4-1 (32.74 mmol, 74.68%) was obtained by column column separation. Preparation of Compound 4-2 10 g of Compound 4-1 (32.74 mmol) was mixed with 100 mL of triethyl phosphite, and stirred at 150 ° C for 7 hours. The mixture was cooled at room temperature and subjected to distillation under reduced pressure and then recrystallised from ethyl acetate to afford 7 g of compound 4-2 (25.60 mmol, 78.19%). Preparation of compound 32 7g of compound 4-2 (25.6〇mmol), l〇.44g of N-(4-bromophenyl)-N,9-diphenyl-9-carboxamide (51.21mmol), 2.5 g of Cul (12.80 mmol), l6.3 g of K3P〇4 (76.82 mmol), and 2 mL of toluene were mixed and heated at 50 °C. mmL ethylenediamine (25.60 mmol) was added to the mixture. The mixture was stirred at reflux for 12 hr then cooled over EtOAc. The resulting material was washed with a NaHC03 solution. After the water gas was removed by MgS04, 'distillation under reduced pressure' was separated by column column to give 8 g of compound 32 (22.89 mmol, 89.41%). MS/FAB measured value 682 'calculated value 681.84. [Preparation Example 5] Preparation of Compound 41 52 95328 201213504

Preparation of Compound 5-I 5 g of 2-(phenylamino)benzoic acid (0.23 mol) was dissolved in 1 L of MeOH. The mixture was placed in an ice bath and stirred for 1 hr. After slowly adding 60 mL of SOC12 (0.58 mol) at 〇 °C, the mixture was at 9 Torr.授 Return and mix for 12 hours. After the completion of the reaction, the resulting mixture was washed with water and washed with acetic acid. The organic layer moisture was removed with MgS 4 and the solvent was removed on a rotary evaporator, and then purified by column chromatography using ethyl acetate as a solvent to afford 47 g of Compound 5-1 (92%). Preparation of Compound 5-2 After 90 g of compound 5-1 (0.3 mol) was added to 1.5 L of THF, 462 mL of MeMgBr (3.0 M) (1.38 mol) was slowly added to the mixture, and the mixture was stirred at room temperature 12 hour. After the reaction was completed, the resulting mixture was evaporated to water and extracted with ethyl acetate. The organic layer water 1 ' was removed with MgS04 and the solvent was removed on a rotary evaporator, and then purified by column chromatography using ethyl acetate as a solvent to afford 80 g of compound 5-2 (90%). Preparation of compound 5-3 After 8 g of compound 5-2 (0, 35 mol) was added to 1.7 L of H3P〇4, mixture 53 95328 201213504 was stirred at room temperature for 12 hours. After completion of the reaction, the resulting mixture was treated with distilled water, and the obtained solid was filtered and washed with water. The solid was dissolved in dioxane to be extracted and neutralized with NaOH. The organic water vapor was removed with MgS〇4, and the solvent was removed by a rotary evaporator, and then recrystallized using hexane to obtain 64 g of compound 5-3 (87%). Preparation of compound 5-4 64 g of compound 5-3 (0.30 mol), 52.8 g of benzene bromide (〇.33 mol), 1.37 g of Pd(OAc) 2 (6.11 mmol), 7.3 mL of 50% P (t- Bu) 3 (15.28 mmol), and 58 g of NaOt-Bu (0.61 mol) dissolved in 1.2 L of toluene' mixture were stirred at 120 ° C for 12 hours. After completion of the reaction, the resulting mixture was taken up in distilled water and extracted with ethyl acetate. The organic layer of water was removed with MgS04 and the solvent was removed on a rotary evaporator, and purified by column chromatography using ethyl acetate as a solvent to afford 71 g of compound 5-4 (81%). Preparation of Compound 5-5 20 g of Compound 5-4 (〇.〇7 mol) was dissolved in 800 mL of DMF and stirred at 0 ° C for 10 min. After slowly adding 12.5 g of NBS (0.07 mol) in 350 mL of DMF, the mixture was stirred at 〇〇c for 6 hours. After the completion of the reaction, the resulting mixture was neutralized with distilled water and extracted with ethyl acetate. The organic layer moisture was removed with a MgSCU, and the solvent was removed by a rotary evaporator, and purified by column chromatography using ethyl acetate as a solvent to afford 21 g of compound 5-5 (84%). Preparation of compound 5-6 20 g of compound 5-5 (0.054 mol), 8.4 g of 2-chloroaniline (0.065 54 95328 8 201213504 mol), 370 mg of Pd(OAc) 2 (1.64 mmol), 50% of 3.6 mL P(t-Bu)3 (5.49 mmol)' and 35.7 g of Cs2C03 (0.109 mol) were dissolved in 300 mL of toluene and stirred at 120 ° C for 4 hours. After the reaction was completed, the resulting mixture was combined with distilled water and extracted with ethyl acetate. The organic water vapor was removed with MgS04, and the solvent was removed by a rotary evaporator, and then purified by column chromatography using ethyl acetate as a solvent to obtain 13.6 g of compound 5-6 (60%). Preparation of compound 5-7 12.6 g of compound 5-6 (〇.〇3 mol), 1.37 mg of Pd(OAc) 2 (6.13 mmol), 3 g of bis(t-butyl)(fluorenyl)tetrafluoroborate scale (12.26) Methyl), and 50 g of Cs2CO3 (0.15 mol) were dissolved in 240 mL of DMA and stirred at 190 °C for 4 hours. After the reaction was completed, the resulting mixture was combined with distilled water and extracted with ethyl acetate. The organic layer moisture was removed with MgS04, and the solvent was removed by a rotary evaporator, and then purified by column chromatography using ethyl acetate as a solvent to obtain 7 g of compound 5-7 (70%). Compound 5-7 (25.60 mmol), 10.44 g of N-(biphenyl-4-yl), N-(4-alkaline phenyl)-9,9-dimercapto-9HU-amine (51.2 mmol) 2.5 g of Cul (12.80 mmol), 16.30 g of K3P〇4 (76.82 mmol), and 20〇1111^曱benzene were mixed at 50. (3). 1.721111 / ethylenediamine (25.60 mmol) was added to the mixture. After the mixture was stirred at reflux for 12 hours, the mixture was cooled to room temperature and extracted with ethyl acetate. The obtained material was NaHC? After the water gas was removed by MgS 4 , it was subjected to distillation under reduced pressure and separated by column 20113504 to obtain 8 g of compound 41 (22.89 mmol, 89.41 〇 / 0). MS/FAB found 811, calculated 810.04. 6] Preparation of Compound 51

Preparation of Compound 6-1 8.1 g of Compound 2-2 (0.028 mol) was added to 1 L of 2 neck RBF, and 300 mL of DMF was added to the mixture. The mixture is in a mortar. The mixture was refluxed for 10 minutes. 5.08 g of NBS (0.028 mol) was dissolved in 3 mL of DMF' and the mixture was slowly added to the reaction mixture, and the mixture was subjected to reflux for 6 hours. After the completion of the reaction, the resulting mixture was evaporated to dryness and extracted with ethyl acetate. The organic layer moisture was removed with MgS(R)4, and the solvent was removed on a rotary evaporator, and then purified by column chromatography using ethyl acetate as a solvent to obtain 9 g of Compound 6-1 (87%). Preparation of Compound 6-2 7 g of Compound 6-1 (18.30 mmol), 13.7 g of the genus (4-Benzene) N, phenylnaphthalen-2-amine (36.60 mmol), 1.7 g of Cul (9.i5 mmol) ), 6 g of K3P〇4 (54.90 mmol), and 10 mL of toluene were mixed and heated at 5 °c. 1.2 mL of ethylenediamine (18.30 mmol) was added to the mixture and stirred in a reflux. After 14 hours, the mixture was allowed to cool at room temperature, and distilled water was added to the mixture. The resulting mixture was extracted with ethyl acetate. After removing water 95328 56 201213504 with MgS〇4, distillation under reduced pressure was carried out through a column to obtain 8 g of compound 6-2 (17.44 mmol, 95.33%). • Preparation of compound 51 • 7 g of compound 6-2 (18.30 mmol), 13.7 g of 9 Η-σ carbazole (36.60 mmol), 1.7 g of CuI (9.15 mmol), 11.6 g of Κ3ΡΟ4 (54.90 mmol), and l 〇〇mL曱 benzene was mixed and heated at 50 °C. 1.2 mL of ethylenediamine (18.30 mmol) was weighed into the mixture and mixed under reflux. After 14 hours, the mixture was allowed to cool at room temperature, and distilled water was added to the mixture. The mixture was extracted with ethyl acetate. After removing the water vapor with MgS04, the mixture was evaporated under reduced pressure, and then separated by a column to obtain 8 g of Compound 51 (17.44 mmol, 95.33%). MS/FAB found 742, calculated 741.92. [Preparation Example 7] Preparation of Compound 53

74 g of 2-bromodibenzo[b,d]thiophene (216.3 mmol) was dissolved in 1.5 L of THF, and 86.5 mL of n-butyllithium (216.3 mmol, 2.5 M in hexane) was slowly added at -78 °C. Burning). After 1 hour, 28.9 mL of trimethyl borate (259.6 mmol) was added to the mixture and stirred at room temperature for 12 hours. Distilled water was added to the mixture, and the mixture was extracted with ethyl acetate. To 57 95328 201213504

After removing the moisture from the MgS 4, the mixture was evaporated under reduced pressure, and recrystallized from ethyl acetate and ethylbenzene to give 40 g of Compound 7-1 (136.8 mmol, 62.96%). Preparation of compound 7-2 40 g of compound 7-1 (136.8 mmol), 37.4 g of deuterated nitro stupid (150.5 mmol), 6.32 g of Pd(PPh3)4 (5.47 mmol), 170 mL of 2M Na2CO3, and 700 mL of toluene Mix and mix at 1 inch. Stir for 4 hours. After the mixture was allowed to cool at room temperature, water was added to the mixture, and the mixture was extracted with ethyl acetate. After removing the water vapor with MgS 4 , the mixture was evaporated under reduced pressure and then purified to give 28 g of Compound 7-2 (72.86 mmol, 52.94%). Preparation of Compound 7-3 28 g of Compound 7-2 (72.86 mmol) was mixed with 300 mL of triethyl phosphite, and spoiled at 150 ° C for 12 hours. After cooling at room temperature and subject to reduced pressure, the mixture was extracted with ethyl acetate, and the obtained material was washed with the obtained material. After removing the water vapor with MgS〇4, the mixture was depressurized and separated by a column to obtain llg of compound 7-3 (31.22 mmol, 43.05%). Preparation of Compound 53 7 g of compound 7-3 (18.30 mmol), 13.7 g of 4·bromo-N-(4-(dibenzo[b,d]°ephen-4-yl)phenyl)-N Phenylaniline (36.60 mmol), 1.7 g of CuI (9.15 mmol), 11.6 g of K3P〇4 (54.90 mmol), and 100 mL of toluene were mixed and heated at 50 °C. Add i.2 ml of ethylenediamine (18.30 mmol). and stir at reflux. After 14 hours, the mixture was allowed to cool at room temperature and steamed water was added to the mixture. The mixture was extracted with acetic acid. After removing water vapor with MgS〇4, distillation under reduced pressure was carried out through a column to obtain 8 g of Compound 53 (17.44 mmol, 95.33%). 95328 58 201213504 MS/FAB measured value 699, calculated 698.90. [Preparation Example 8] Preparation of Compound 54

Preparation of Compound 8-1 50 g of 2,5-dibromonitrobenzene (177.99 mol), 36.7 g of 1-naphthoic acid (213.59 mmol), 10.28 g of Pd(PPh3)4 (8.89 mmol), 2M Na2C03 (533.97 mmol), 700 mL of toluene was mixed with 200 mL of ethanol, and stirred at 10 ° C for 5 hours. After cooling at room temperature and adding distilled water to the mixture, the mixture was extracted with ethyl acetate. After removing water vapor with MgS 4 , distillation under reduced pressure was carried out through a column to obtain 50 g of Compound 8-1 (152.36 mmol, 85.60%). Preparation of Compound 8-2 50 g of Compound 8-1 (152.36 mm 〇l) was mixed with 500 mL of triethyl phosphite, and the mixture was stirred at 150 ° C for 7 hours. After the mixture was cooled at room temperature and distilled under reduced pressure, the mixture was extracted with ethyl acetate. The resulting material was washed with distilled water. After removing the water gas with MgS 4 , the mixture was evaporated under reduced pressure, and then purified by column column, </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> </ RTI> <RTIgt; Preparation of compound 8-3 30 g of compound 8-2 (101.29 mmol), 41.3 g of N-(4:(9H-carbazol-9-yl)phenyl)-4-bromo-N-(4-third Butyl-styl)aniline (202.59 mmol), 9.6 g of Cul (50.64 mmol), 82.5 g of Cs2C03 (253.2 mmol), and 600 mL of benzene were mixed and heated at 50 °C. 6.8 mL of ethylenediamine (101.29 mmol) was added and the mixture was stirred at reflux. After 14 hours, the mixture was allowed to cool at room temperature, and distilled water was added to the mixture. The mixture was extracted with ethyl acetate. The water vapor was removed by MgS04, and the mixture was evaporated under reduced pressure, and then purified by column chromatography to afford 32 g of Compound 8-3 (85.96 mmol, 84.86%). Preparation of compound 8-4 32 g of compound 8-3 (85.96 mmol) were dissolved in 300 mL of THF. and 37.8 mL of n-butyl chain (94.55 mmol, 2.5 Μ in hexane) was slowly added at -78 °C. After 1 hour, 12.4 mL of tridecyl borate (111.7 mmol) was added to the mixture. After the mixture was stirred at room temperature for 12 hours, distilled water was added to the mixture, and the mixture was extracted with ethyl acetate. After removing water vapor with MgS〇4, distillation under reduced pressure was carried out through a column to obtain 2 g of compound 8-4 (59.31 mmol, 69.00%). Preparation of Compound 8-5

20 g of compound 8-4 (59.31 mmol), 14.3 g of 1-bromo-2-; ε-succinylbenzene (71.17 mmol), 2.7 g of Pd(PPh3)4 (2.37 mmol), 75 ml of 2M

Na2C03, 300 mL of toluene, and 70 mL of ethanol were mixed and fed under reflux. After 5 hours, the mixture was allowed to cool at room temperature, and distilled water was added to the mixture of 95328 8 60 201213504. The mixture was extracted with ethyl acetate. The water gas was removed with MgS 4 and distilled under reduced pressure, and then separated by a column to obtain 20 g of compound 8-5 (48.25 mmol, 81.36%). Preparation of Compound 8-6 20 g of Compound 8-5 (48.25 mmol) was mixed with 200 mL of triethyl sulphate and stirred at 150 C for 6 hours. The mixture was cooled at room temperature and distilled under reduced pressure. The resulting material was washed with distilled water. After removing the water vapor with MgS 4 , the mixture was distilled under reduced pressure and separated through a column to obtain 7 g of compound 8-6 (18.30 mmol, 37.93%). Preparation of compound 54 30 g of compound 8-6 (1〇 1.29 mmol), 41.3 g of benzene (202.59 mmol), 9.6 g of Cul (50.64 mmol), 82.5 g of Cs2C03 (253.2 mmol)' and 600 mL of toluene were mixed. And heated at 50 °C. 6.8 mL of ethylenediamine (101.29 mmol) was added to the mixture and the mixture was refluxed. After 14 hours, the mixture was allowed to cool at room temperature, and distilled water was added to the mixture. The mixture was extracted with ethyl acetate. The water vapor was removed with MgS04, and subjected to distillation under reduced pressure, and then separated by a column to obtain 32 g of Compound 54 (85.96 mmol, 84.86%). MS/FAB found 848, calculated 847.06. [Preparation Example 9] Preparation of Compound 58 61 95328 201213504

Preparation of Compound 9-1 10.2 g of 1-naphthyl succinic acid (59.4 mmol), 10 g of 〇g 演 石 石 石 基 4 (49.5 mmol), 1.7 g of Pd(PPh3) 4 (1.4 mmol) 70 ml of a 2ΜΚ2〇〇3 aqueous solution, 200 mL of hydrazine and 1 mL of ethanol were mixed and stirred under reflux for 12 hours. The mixture was washed with steam and taken up in ethyl acetate. After removing the water vapor in anhydrous MgS 4 and performing distillation under reduced pressure, the residue was separated through a column to obtain 9.0 g of Compound 9-1 (73.7%). Preparation of compound 9-2 9.0 g of compound 9-1 (36.1 mmol) and 7.6 g of η-brominated amber iminoimide (43.3 mmol) were dissolved in 300 mL of dichlorohydrazine and stirred at room temperature for 12 hours. . The solid obtained by distillation under reduced pressure was washed with distilled water, hexane, and hexane to obtain 9.6 g of compound 9-2 (81.3%). Preparation of compound 9-3 9.6 g of compound 9-2 (29.3 mmol) was mixed with 72.2 g of Fe[C204] · 62 95328 8 201213504 2H20 (iron oxalate dihydrate) (175.5 mmol) and heated at 205 ° C. 30 minutes. After the mixture was allowed to cool at room temperature, the mixture was extracted with ethyl acetate, and the obtained material was washed with distilled water. After recrystallization using toluene, 5.2 g of compound 9-3 (60.5%) was obtained. Preparation of compound 9-4 30 g of compound 9-3 (101.29 mmol), 41.3 g of 4-bromo-N-phenyl-yi(4-(9-phenyl-911-oxazol-3-yl)phenyl Aniline) (202.59111111〇1), 9.6 g of Cul (50.64 mmol), 82.5 g of Cs2C03 (253.2 mmol), and 600 mL of hydrazine were mixed and heated at 50 °C. 6.8 mL of ethylenediamine (101.29 mmol) was added to the mixture and the mixture was refluxed. After 14 hours, the mixture was allowed to cool at room temperature, and distilled water was added to the mixture. The mixture was extracted with ethyl acetate. The water vapor was removed by MgS04, and the mixture was distilled under reduced pressure. After separation by column, 32 g of compound 9-4 (85.96 mmol, 84.86%) was obtained. Preparation of compound 9-5 23.1 g of compound 9-4 (62.07 mmol) was dissolved in 500 mL of THF' and 29.79 mL of n-butyl (74.48 mmol, 2.5 M in hexane) was slowly added at -78C. Into the mixture. After 1 hour, 10.38 mL of trimethyl borate (93.1 Ommol) was added to the mixture. After the mixture was spoiled at room temperature for 12 hours, steamed water was added to the mixture, and the mixture was extracted with ethyl acetate. The water vapor was removed with MgS04, and the mixture was evaporated under reduced pressure. After recrystallization from ethyl acetate and hexane, 14 g of compound 9-5 (67%) was obtained. Preparation of compound 9-6 14 g of compound 9-5 (41.79 mmol), 13.51 g of methyl-2- desertification 63 95328 201213504 benzoic acid g (45.97 mmol), 1.9 g of Pd(PPh3) 4 (1.67 Methyl), 60 mL of 2M Na2C03' and 2 mL of hydrazine were mixed and stirred at reflux. After 12 hours, the mixture was allowed to cool at room temperature, and distilled water was added to the mixture. The mixture was extracted with ethyl acetate. The water vapor was removed by MgS04, and after distillation under reduced pressure, after separation by a column, 8.8 g of compound 9-6 (42%) was obtained. Preparation of compound 9-7 8.8 each compound 9-6 (17.53111111〇1) was dissolved in 20〇1111^1'1^, and 14.60mL sulfhydryl desertification town (43.82mmol, 3.0M in the test) ) added to the mixture. The mixture was heated at 60 °C. After 6 hours, the mixture was allowed to cool at room temperature and added to the steaming water. The mixture was extracted with ethyl acetate. After removing the water vapor with MgS〇4, distillation under reduced pressure was carried out, and 6 6 g of the compound 9-7 (74%) was obtained by column separation. Preparation of Compound 58

6.6 g of compound 9-7 (13.14 mmol), 50 mL of acetic acid and 50 mL of acid were mixed and stirred at 50 C for 5 hours. The mixture was allowed to cool at room temperature and neutralized with a NaOH solution. The mixture was extracted with ethyl acetate. After removing the water vapor with MgS〇4, distillation under reduced pressure was carried out, and 5.lg compound 58 (80%) was obtained by column chromatography. MS/FAB found 819, calculated 818.01. [Preparation Example 10] Preparation of Compound 122

64 95328 8 201213504 Preparation of Compound 10-1 60 g of 2-bromo-9,9·didecyl-9H-((.219 mol), 56 g of 2-chloroaniline (0.439 mol), 1.5 g of Pd (OAc) 2 (0.006 mol), 14 mL of P(t-Bu)3 (0.021 mol), and i43 g of CsCO3 (0.439 mol) were mixed, and 600 mL of toluene was added to the mixture. The mixture was stirred at i2 ° C for 12 hours. After the completion of the reaction, the obtained material was washed with distilled water and extracted with ethyl acetate. The organic layer moisture was removed with MgS04, and the solvent was removed by a rotary evaporator, and then purified by column column to obtain 65 g of Compound 10-1 (92%). Preparation of Compound 10-2 1000 mL of DMA was added to 65 g of Compound 10-1 (0.20 mol), 2.3 g of Pd(OAc) 2 (0.01 mol), and 5.9 g of bis(t-butyl)(fluorenyl) four. In a mixture of fluoroboric acid scales (〇.〇2 mol) and 64 g of Na2CO3 (0.60 mol), the mixture was stirred at 190 ° C for 16 hours. After the reaction was completed, the obtained material was washed with distilled water and extracted with ethyl acetate. The organic gas of the organic layer was removed with MgS04, and the solvent was removed by a rotary evaporator, and then purified by column to obtain 3 g of compound 10-2 (54%). Preparation of Compound 10-3 130 mL of toluene was added to 17 g of compound 1 〇·2 (〇.〇61ιηο1), 2.3 g of Cul (0.012 mol), 3.3 mL of ethylenediamine (〇.〇49 mol) and 16 g of K3P〇 In a mixture of 3 (〇.〇74 mol), the mixture was stirred at 120 ° C for 12 hours. After the reaction was completed, the obtained material was washed with distilled water and extracted with ethyl acetate. The organic layer moisture was removed with MgS04, and the solvent was removed by a rotary evaporator, and then purified by column column to obtain 7.8 g of compound (72%). Preparation of Compound 122 65 95328 201213504 4 g of compound 10-3 (0.009 mol), 3.1 g of 4-(diphenylamino)phenyl phenyl acid (O.O.Omol), 527 mg of Pd(PPh3)4 (〇. A mixture of 4 mmol), 14 mL of K2C03 (2M), 14 mL of EtOH and 28 mL of toluene was stirred at 120 ° C for 8 hours. After the reaction was completed, the obtained material was washed with distilled water and extracted with ethyl acetate. The organic layer moisture was removed with MgS(R) 4, and the solvent was removed by a rotary evaporator, and then purified by column to obtain 2.6 g of Compound 122 (47%). MS/FAB measured value 603, calculated 602.76. [Preparation Example 11] Preparation of Compound 132

Preparation of compound 11-1, 10 g of compound 4-2 (36.6 mmol), 20 g of 峨-4- evolutionary stupid (73.2 mmol), 3.5 g of CuI (18.3 mmol), 4-5 mL of ethylenediamine (73.2 mmol), A mixture of 19.4 g of K3P04 (91.5 mmol) and 200 mL of toluene was spoiled overnight at 120-C. After the reaction was completed, the obtained material was washed with distilled water and extracted with ethyl acetate. The organic layer water was removed with MgS 4 and the solvent was removed by rotary evaporator to afford 7.7 g of compound 11-1 (49%). 66 95328 8 201213504 Preparation of Compound 132 7 g of compound ll-i (i6.3 mmol), 5.6 g of 4·(diphenylamino)phenylboronic acid (19.6 mmol), 〇.95 g of Pd(PPh3)4 ( A mixture of 0.82 mmol), 6 g of K2C03 (40.8 mmol), 60 mL of toluene, 20 mL of EtOH and 20 mL of H20 was placed on the loot: stirring overnight. After the reaction was completed, the obtained material was washed with distilled water and extracted with ethyl acetate. The organic water vapor was removed with MgS04, and after removing the solvent by a rotary evaporator, 5.4 g of compound 132 (56%) was obtained by column purification. MS/FAB found 593, 592.75. The following compounds were prepared according to Preparations 1 to 11.

67 95328 201213504 Migratory intermediate A intermediate Β MS/FAB measured value 14 ο?ταΝ^χ° Φ Br ό 819 818.34 19 9 αΝχ% Φ Βγ 692 691.30 20 9 αΝχ% Φ Br Q 741 740.29 31 °φ . Βγ 537 536.30 68 95328 8 201213504

69 95328 201213504

[Example 1] Production of OLED device using the organic electroluminescent compound of the present invention An OLED device was produced using the electroluminescent material of the present invention. First, the transparent ITO film (15 Ω/[Ι1) taken from OLED (manufactured by Samsung Corning) glass was cleaned with ultrasonic waves using trichloroethylene, acetone, ethanol, and steaming water, and stored in a different state before use. In propanol. Thereafter, the ITO substrate was assembled in a substrate holder of a vacuum deposition apparatus, and 2-ΤΝΑΤΑ (4,4',4&quot;_参(Ν,Ν_(2•naphthyl)phenylamino)triphenyl The amine is placed in one of the chambers of the vacuum deposition apparatus and then evacuated to bring the chamber to a tor vacuum. Thereafter, a current is applied to the chamber to evaporate 2_τν·ΑΤΑ, so that a hole having a thickness of 6 nanometers (nm) is formed on the substrate to inject 70 95328 8 201213504 layer, and then the compound 1 is placed in the vacuum vapor deposition apparatus. In another small t, a current is applied to the cell to evaporate the compound 1, and a hole transport layer having a thickness of 20 nm is formed on the hole injection layer. • (4) After the m-layer and the hole transport layer, an electric field light-emitting layer is continuously formed thereon. Place the coffee [4, 4, Che, _ 吟 吟 w_ biphenyl] as the main body in the chamber of the vacuum deposition device 'and (piq) 2Ir (acac) [double _ (Im phenyl phenyl) Ethyl acetonide silver (10) was placed as a dopant in the other chamber of the vacuum vapor deposition apparatus. The two materials were evaporated at different rates, whereby an electric field luminescent layer having a thickness of 30 nm was vapor-deposited on the hole transport layer with 4 wt% doping. Thereafter, BAlq (bis(2-mercapto-8-hydroxyquinolinyl)(p-phenylphenolyl)aluminum (ΠΙ)) having a thickness of 1〇11〇1 is vapor-deposited on the electroluminescent layer as electricity. Hole blocking layer. As the electron transport layer, Alq3 (8-hydroxyquinoline)-aluminum (ΠΙ) having a thickness of 2〇11111 was vapor-deposited on the electroluminescent layer. Thereafter, Liq (lithium quinolate) having a thickness of 1 nm was deposited as an electron injecting layer, and another aluminum deposition apparatus was used to form an aluminum (A1) cathode having a thickness of 150 nm to fabricate an OLED. Each compound used in the 0 LED was purified by vacuum sublimation at 10·6 torr. As a result, it was confirmed that a current of 13.8 milliamperes (mA) per square centimeter (cm 2 ) at a voltage of 6.9 volts (V) was emitted, and a red light of 1020 turbid light (cd)/m 2 was emitted. [Example 2] Production of OLED device using organic electroluminescent compound of the present invention An OLED device was manufactured in the same manner as in Example 1 except that Compound 19 was used as a hole transporting material. As a result, it was confirmed that a current of 14.3 mA/cm2 was obtained at a voltage of 6.7 V, and a red light of 1060 cd/m2 was emitted. [Example 3] Production of OLED device using organic electroluminescent compound of the present invention An OLED device was manufactured in the same manner as in Example 1 except that Compound 31 was used as a hole transporting material. As a result, it was confirmed that a current of 13.9 mA/cm2 was obtained at a voltage of 6.7 V, and a red light of 1044 cd/m2 was emitted. [Example 4] Production of OLED device using organic electroluminescent compound of the present invention An OLED device was manufactured in the same manner as in Example 1 except that Compound 69 was used as a hole transporting material. As a result, it was confirmed that a current of 14.2 mA/cm2 was obtained at a voltage of 6.8 V, and a red light of 1015 cd/m2 was emitted. [Example 5] Production of an OLED device using the organic electroluminescent compound of the present invention was changed except that Compound 1 was used as a hole transporting material, and an organic ruthenium complex Ir(ppy) 3 was used [Paran (2-phenylindole) A pyridine device was produced in the same manner as in Example 1 as an electric field luminescent dopant, which was doped outside the electroluminescent layer at 15% by weight. As a result, it was confirmed that a current of 3.8 mA/cm2 at a voltage of 6.6 V was able to emit green light of 1065 cd/m2. [Example 6] OLED device using the organic electroluminescent compound of the present invention 72 95328 201213504 Production The OLED device was fabricated in the same manner as in Example 5 except that Compound 20 was used as the hole transporting material. As a result, it was confirmed that a current of 3.9 mA/cm2 at a voltage of 6.6 V was able to emit green light of 1070 cd/m2. [Example 7] Production of OLED device using organic electroluminescent compound of the present invention An OLED device was manufactured in the same manner as in Example 5 except that Compound 31 was used as a hole transporting material. As a result, it was confirmed that a current of 3.7 mA/cm2 at a voltage of 6.7 V was able to emit green light of 1085 cd/m2. [Example 8] Production of OLED device using organic electroluminescent compound of the present invention An OLED device was manufactured in the same manner as in Example 5 except that Compound 42 was used as a hole transporting material. As a result, it was confirmed that a current of 3.5 mA/cm2 was generated at a voltage of 6.6 V, and green light of 1055 cd/m was emitted. [Example 9] Production of OLED device using organic electroluminescent compound of the present invention An OLED device was manufactured in the same manner as in Example 5 except that Compound 43 was used as a hole transporting material. As a result, it was confirmed that a current of 3.6 mA/cm2 at a voltage of 6.6 V was able to emit green light of 1080 cd/m2.

[Example 10] OLED using the organic electroluminescent compound of the present invention 73 95328 201213504 The manufacture of the device was changed to the use of the compound 14 in place of the 4,4,4"-parameter (N,n_(2^a)phenylamino group The triphenylamine (2-TNATA) was used as the hole transporting material, and the OLED device was fabricated in the same manner as in Example 5. As a result, it was confirmed that the current was 3.7 mA/cm2 at a voltage of 6.6 V, and 1050 was issued. Green light of cd/m2 [Example 11] The manufacture of the 〇led device using the organic electroluminescent compound of the present invention uses NW'H,-biphenyl]_4,4,_diyl) bis (Nl_(Cai Xiaoji n4, n4-Diphenylbenzene_M-diamine) is used as a hole injection material, and then evacuated to a vacuum of 10-6 t〇rr in the chamber. Then, a current is applied to the chamber to evaporate NWH,-biphenyl hydrazine, 4, _diyl) bis (N1 (Cai Xiaoji) _n4, n4 diphenylbenzene-1,4_diamine' thus forms a hole injection layer of 60 mn thickness on the 1T0 substrate. Then 'the compound 122 is placed In another chamber of the vacuum vapor deposition apparatus, it applies a current to the chamber to evaporate the compound, thereby forming a hole thickness of 2 〇 on the hole in the layer. After opening/forming. After the hole/main layer and the hole transport layer, the electric field layer is continuously formed on it. H.31 is added as the main body in the J chamber of the vacuum deposition device. D_58 is placed as a dopant in another chamber, and the material is used as a surface material at different rates, so that the electric field luminescent layer having a thickness of 3 Å is vapor-deposited on the hole transport layer by doping with Μ% by weight. Then 2 (4_(9,1〇_bis(naphthalene 2yl) onion 2 base) phenyl) small phenyl-1H-benzene is just added to the chamber of the human hole transport layer and in another chamber The secret (four) bell). Evaporate the two chambers at the same rate, 95328 74 201213504 and deposit a hole transport layer with a thickness of 30 nm with 50% by weight doping. After that, the vapor deposition thickness is 1 nm. 8 - via Liq as an electron injection layer, and using another vacuum deposition device to form an A1 cathode with a thickness of 150 nm to fabricate an OLED. Each compound used in the OLED is L〇_6torr was purified by vacuum sublimation. The result was confirmed to have a current of 11.5 inA/cm2 at 5.4 V and 6200 cd/m2 [Example 12] Manufacture of an OLED device using the organic electroluminescent compound of the present invention, except that Compound 132 was used as a hole transporting material, H-1 was used as a host, and D-71 was used as a dopant. An OLED device was fabricated in the same manner as in Example 11. As a result, it was confirmed that a current of 6.32 mA/cm2 was applied at a voltage of 4.0 V, and green light of 3300 cd/m2 was emitted. [Example 13] Production of OLED device using organic electroluminescent compound of the present invention In addition to modification to use of compound 138 as a hole transport material, H-34 as a host, and D-31 as a dopant, according to Examples The same method of 11 manufactures an OLED device. As a result, it was confirmed that a current of 2.8 mA/cm2 at a voltage of 3.6 V was able to emit green light of 1500 cd/m2. [Example 14] Production of OLED device using the organic electroluminescent compound of the present invention 75 95328 201213504 Except that the compound 149 was used as a hole transport material, H-39 was used as a host, and D-31 was used as a dopant. An OLED device system was fabricated in the same manner as in Example 11. As a result, it was confirmed that a current of 1.59 mA/cm2 was applied at a voltage of 3.1 V, and green light of 500 cd/m2 was emitted. [Example 15] Production of an OLED device using the organic electroluminescent compound of the present invention was changed except that Compound 109 was used as a hole transporting material, H-45 was used as a host, and D-6 was used as a dopant (mixed at 4% by weight). An OLED 'device was fabricated in the same manner as in Example 11 except for the hybrid. As a result, it was confirmed that the current was 7.5 mA/cm2 at a voltage of 4.0 V, and a red light of 1065 cd/m2 was emitted. [Example 16] Production of OLED device using the organic electroluminescent compound of the present invention, except that the compound 141 was used as a hole transporting material, H-49 was used as a host, and D-6 was used as a dopant, according to Examples The same method of 15 manufactures an OLED device. As a result, it was confirmed that a current of 17.0 mA/cm2 was generated at a voltage of 5.2 V, and a red light of 2210 cd/m2 was emitted. [Example 17] Production of OLED device using organic electroluminescent compound of the present invention In addition to the use of compound 142 as a hole transport material, H-52 as a host, and D-6 as a dopant, according to Examples The same method of 15 manufactures an OLED device. 76 95328 201213504 As a result, it was confirmed that there was a current of 32.1 mA/cm2 at a voltage of 5.6 V, and a red light of 370 〇cd/m2 was emitted.

[Example 18] OLED* device using the organic electroluminescent compound of the present invention. * In addition to using compound I49 as a hole transport material, H-53 as a host, and D-9 as a dopant, An OLED device was fabricated in the same manner as in Example 15. As a result, it was confirmed that a current of 12.9 mA/cm2 was generated at a voltage of 6.0 V, and red light of 1710 cd/m2 was emitted. [Comparative Example 1] Manufacture of an OLED device using a prior art electroluminescent material was changed to use bis(α-naphthyl)-N,N'-diphenyl-4 in a chamber of a vacuum vapor deposition apparatus. 4'-Diamine [NPB] An OLED device was produced in the same manner as in Example 1 except that the present invention was used as a hole transporting material. As a result, it was confirmed that there was a current of 20.0 mA/cm2 at a voltage of 8.2 V, and a red light of 1000 cd/m2 was emitted. [Comparative Example 2] Manufacture of OLED using the prior art electroluminescent material was changed to use NM, bis(α-naphthyl)-N,N'-diphenyl in one of the chambers of the vacuum vapor deposition apparatus. An OLED device was produced in the same manner as in Example 5 except that the base 4,4'-diamine [NPB] was used as the hole transporting material instead of the chemical of the present invention. As a result, it was confirmed that a current of 5.0 mA/cm 2 was obtained at a voltage of 6.0 V, and a green light of 1183 cd/m 2 was emitted at 95328 77 201213504. [Comparative Example 3] Manufacture of an OLED device using the prior art electroluminescent material except that NPB was used as a hole transporting material, H·1 as a main body, and D-30 as a dopant, according to Example U The OLED device was fabricated in the same manner. As a result, it was confirmed that there was a current of 4.62 mA/cm2 at a voltage of 3.0 V, and a green light of 1000 cd/m2 was emitted. [Comparative Example 4] Manufacture of an OLED device using the prior art electroluminescent material

An OLED device was mainly fabricated in accordance with Example 15 except that NPB was used as the hole transporting material, as the body 'and D-9 as the dopant. As a result, it was confirmed that a current of 13.2 was emitted at a voltage of 4.6 V and a red light of 1000 cd/m2 was emitted. Compared with the conventional materials, it was confirmed that the organic electro-p compound developed by the present invention exhibited high electric field luminescence properties. The organic per luminescent compound of the present invention effectively blocks the triplet excitables from the luminescent layer by increasing the triplet. Therefore, since the state illuminating efficiency is high, a very excellent extravagant electric field can be manufactured. Although the more specific embodiment of the present invention is disclosed as a two-position. However, those having ordinary skill in the art should understand that various materials, additions and substitutions can be made to the medical embodiment of the invention without departing from (4) and ^ attached to the contents of the present invention as defined by the scope of the patent. Application 95328 78 201213504 [Simple description of the diagram] No [Main component symbol description]

Claims (1)

201213504 VII. Patent application scope: 1. An organic electric field luminescent compound represented by the following chemical formula: Chemical formula 1 ΑΓ! m(Ri) Wherein ring A and ring C are independently represented Ring B indicates that Χι and x2 independently represent CR3 or N; Υι and Y2 independently represent a chemical bond, _〇_, _s_, _c(RiiRi2)_, -Si(R]3RH)- or -Ν^5)-, excluding Wherein 丫1 and γ2 are both examples of a chemical bond; Ri to I independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6_C3〇) Aryl, substituted or unsubstituted (C2_C3〇)heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted anthracene to 7-membered heterocycloalkane a substituted (C6-C3) aryl (C1-C30) alkyl group, a substituted or unsubstituted (cl_C3〇) alkyl decyl group, a cyano group, a nitro group or a hydroxy group, and is either ^When there are two or more 1 95328 201213504, they are linked to each other to form a cyclic structure; L represents a substituted or unsubstituted (C6_C30) extended aryl group, or substituted or unsubstituted ( C2-C30) heteroaryl, and when L has two or more, they are linked to each other to form a cyclic structure; Ar! and Ar2 independently represent substituted or unsubstituted (C6- C30) aryl, warp Substituted or unsubstituted (C2-C30)heteroaryl or Υ3 and Υ4 independently represent a chemical bond, -Ο-, -S-, -c(r16r17)_, -Si(Ri8Ri9)- or -N(R20)-, excluding an example in which both γ3 and γ4 are chemical bonds; R11 to R2〇 independently represent hydrogen, gas, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6_C3〇) aryl, or substituted or unsubstituted (C2_C3〇)heteroaryl, or each of them may be substituted or unsubstituted (C3-C30) extended or unsubstituted (C3_C3) with or without a fused ring 〇) an alkenyl group and an adjacent substituent chain to form an alicyclic ring and a monocyclic or polycyclic aromatic ring; m and n independently represent an integer of 〇 to 4, and when m and n are 2 or more When a large integer is used, each heart and ^^ may be the same or different from each other; P represents an integer from 0 to 2, and when? When 2, each R 2 may be the same or different from each other; and the heterocycloalkyl, heteroaryl and heteroaryl include one or more selected from the group consisting of B, N, hydrazine, SP (= 〇), Si and P The heteroatoms of the group. 2. The organic electroluminescent compound according to claim 1, wherein 'R1, R2, R3, L, Ari, and each of the substituents represented by Ru to R2 are further advanced. Substituted by one or more substituents selected from the group consisting of hydrazine, dentate, halogen-substituted or unsubstituted (C1-C30) alkyl, (C6-C30) aryl, via (C6_C3〇) An aryl-substituted or unsubstituted (C2-C30)heteroaryl group, a 5- to 7-membered heterocycloalkyl group, a 5- to 7-membered heterocyclic alkyl group slightly bonded to one or more aromatic rings, (C3-C30) cycloalkyl, (C6_C3〇)cycloalkyl, cyano(C2-C30)alkenyl, (C2-C30)alkynyl, carbazolyl, (fused with) one or more aromatic rings C6-C30) aryl (C1-C30) alkyl, (C1-C30)alkyl (C6-C30) aryl, -〇R21, _sr22, -NR23R24, -PR25R26, -SiRnRuR29, nitro and hydroxy, and Yll and γ12 independently represent a chemical bond, -C(R31R32)-, _〇_, _s- or -N(R33)-, excluding an example in which both Υι and Yu are chemical bonds; and R21 to R29, and R31 to R33 independently represents (C1-C30)alkyl, (C6-C30)aryl, (C2-C30)heteroaryl Or (C3-C30) cycloalkyl. 3. The organic electroluminescent compound according to claim 1, wherein the chemical formula 1 Is selected from the following structures: 3 95328 201213504 Among them, the definitions of R2, Ru to Ri5 and P are the same as those defined in the first paragraph of the patent application. 4. The organic electroluminescent compound according to claim 1, which is selected from the group consisting of the following compounds: 4 95328 201213504 5 95328 8 201213504 95328 s 201213504 7 95328 8 201213504 8 95328 201213504 9 95328 8 201213504 10 95328 201213504 11 95328 8 201213504 Q 12 95328 201213504 13 8 201213504 201213504 5. An organic t-field illuminating device comprising the organic electroluminescent compound of any one of claims 1 to 4 15 95328 8 201213504. 6. The organic electroluminescent device according to claim 5, wherein the organic electroluminescent compound is used as a hole injecting material or a hole transporting material. 7. The organic electroluminescent device of claim 6, comprising a first electrode; a second electrode; and one or more organic layers interposed between the first electrode and the first electrode, wherein The organic layer contains one or more organic electroluminescent compounds represented by Chemical Formula 1. 8. The organic electroluminescent device of claim 7, wherein the organic layer further comprises one or more metals selected from the group consisting of: Group 1, Group 2, Period 4, and Section 5. Periodic transition metals, lanthanide metals, and organometallic or complex compounds of d-transition elements. The organic electroluminescent device of claim 7, wherein the organic layer comprises both an electric field luminescent layer and a charge generating layer. 10. The organic electroluminescent device of claim 7, wherein the organic layer further comprises one or more layers of an organic electroluminescent layer emitting red, green and blue light to emit white light. 95328 16 201213504 IV. Designated representative map: (1) The representative representative figure of this case is: (). (There is no picture in this case) (2) A brief description of the symbol of the representative figure: (none) 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: Chemical Formula 1 2 95328