TW201249960A - Novel compounds for organic electronic material and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to a novel compound and an organic electroluminescent device containing the same. The compound according to the present invention has an advantage in manufacturing an organic electroluminescent device which has high luminous efficiency and a long operation lifetime.

Description

201249960 VI. Description of the Invention: [Technical Field of the Invention] The present invention relates to a novel compound for a right enthalpy tape m for an organic electronic material and an organic electric field illuminating device using the same. [Prior Art] An electric field illuminating (EL) device is a self-illuminating device which has advantages in providing a wider viewing angle, higher contrast, and faster response time than other (4) display devices. # From the use of aromatic diamine small molecules and (tetra) compounds as materials for forming the light-emitting layer, Eastman Kodak first developed an organic EL device [Αρρ1· ρ_.匕咐.51, 913, 1987]. The most important factor for determining the luminous efficiency of the organic EL device is the luminescent material. Fluorescent materials have been widely used as luminescent materials to date. However, from the viewpoint of the electric field luminescence mechanism, the phosphorescent material is theoretically shown to have a luminous efficiency four times that of the fluorescent material. Therefore, in recent years, research has been conducted on disc materials. The silver (ΠI) mismatched property is widely recognized as a squama material, including bis((2'-phenyl)-thiophene-N,C3,) 醯(acetamidineacetone)((acac)Ir(btp)2) , 銮 (2-phenylpyridinium pyridine) 铱 (Ir (ppy) 3) and bis (4, 6-difluorophenyl. pyridine-N, C2) Dtt bite silver (Firpic) system as red Light, green and blue light materials. Currently, 4, 4'-N, Ν'-dicarbazole-biphenyl (CBP) is the most widely known host material for phosphorescent materials. Furthermore, Japan Pioneer Company (Pi〇) Neer) et al. developed a high-performance organic EL device using bathocuproine (BCP) and bis(2-mercapto-8-hydroxyquinoline) (4-) used as a barrier material for holes. Phenylphenol) aluminum (in) (BAlq) is used as the host material for 95566 3 201249960. Although these phosphorous host materials provide good luminescent properties, they have the following disadvantages: (1) due to their low glass transition temperature and thermal stability Poor, they may degrade during the vacuum high temperature deposition process. (2) The power efficiency of the organic EL device is measured by [(7Γ/voltage) x current efficiency] And power efficiency is inversely proportional to voltage, therefore, in order to reduce power consumption, power efficiency should be as high as possible. Although organic EL devices containing phosphorescent materials provide higher current efficiency (candle (cd) / ampere than those containing fluorescent materials) (A)) When a conventional material such as BAlq or CBP is used as the phosphorescent host material, a sufficiently high driving voltage is required as compared with an organic EL device using a fluorescent material. Therefore, in terms of power efficiency (lumens (lm)/ There is no advantage in the aspect of the tile (W). (3) Furthermore, the organic EL device has a short service life and still needs to improve its luminous efficiency. The international patent case disclosed in WO Patent Application Publication No. WO 2006/049013 discloses that it has a condensed a bicyclic group as a skeleton structure for a compound of an organic electric field luminescent material. However, it does not disclose a nitrogen-containing fused bicyclic group, and each of the 3-position and the 9-position is coupled with an aromatic ring. A cycloalkyl or heterocycloalkyl-substituted carbazolyl group, and a compound fused with a heterocyclic alkyl group or a cycloalkyl group of an aromatic ring. SUMMARY OF THE INVENTION Problems to be Solved The object of the present invention is to provide a method for Organic electricity a compound of a material having an excellent structure which imparts high luminous efficiency and long service life to the device and has suitable color coordinates; and an organic electric field light having high efficiency and long life using the compound 95566 4 201249960 Means for Solving the Problem The inventors of the present invention found that 'the above-mentioned object can be achieved by the compound represented by the following formula 1:

Wherein, 1 and b are each independently represented by a single bond, substituted or unsubstituted 2 to 30 membered heteroaryl, substituted or unsubstituted (C6-C30) extended aryl, or substituted or Unsubstituted ([6_[30)extension%] Χι means CH or N; Υι and Y2 are individually independent _〇-, _S-, -CReRg- or -NR1Q-; R, to Ri. Individually independently represented by hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted 3 member 30-membered heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted 5 member to gamma heterocycloalkyl, substituted or unsubstituted (C6-C30 An aryl ((n-C30) alkyl group, a (C3-C30) cycloalkyl group fused to at least a di-f-type pen- or a H-substituted (C6-C30) aryl group, and at least one A 5- to 7-membered heterocycloalkyl group fused with a (C6-C30) aromatic ring, and a (C6-C30) aromatic ring thickened with at least one of the urethanes 95566 5 201249960 (C3-C30)cycloalkyl, -NR21R22, -SiR23R24R25, -SR26, -OR27, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) Or alkynyl, cyano, nitro, or hydroxy; or via a substituted or unsubstituted (C3-C30) alkyl or (C3-C30) alkyl group to an adjacent substituent to form one or The plurality of carbon atoms may pass through at least one of the impurities selected from the group consisting of nitrogen, oxygen and sulfur Substituted monocyclic or polycyclic alicyclic or aromatic ring; R2] to R27 have the same definition as one of R1 to Rio; a, b, e, and g are individually independent integers 1 to 4 Wherein, when a, b, e or g is an integer of 2 or more, each Ri, each R2, each Rs or each R7 is the same or different; c, d and f are individually independent representations Integer 1 to 3; wherein, when c, d or f is an integer of 2 or more, each R3, each R4, or each R6 is the same or different; and the heterocycloalkyl group and the (extension) The heteroaryl group contains at least one hetero atom selected from the group consisting of B, N, 0, S, P (=0), Si, and P. Effect of the Invention The compound for an organic electronic material according to the present invention can be manufactured to have high luminous efficiency. The present invention will be described in detail below. However, the following description is intended to explain the present invention, and is not intended to limit the scope of the invention in any way. A compound for an organic electronic material represented by the above formula 1 and an organic electric field light-emitting device comprising the same. 6 201249960 As used herein, "(Cl-C30) (alkyl)" means a straight or branched chain having from 1 to 3 carbon atoms, wherein the number of carbon atoms is preferably 1 to 20 'more preferably 1 to 10' and includes mercapto, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, etc.; r (C2_C3〇) (extension) The term "base" means a straight or branched chain thiol group having 2 to 30 carbon atoms, wherein the number of carbon atoms is preferably from 2 to 20, more preferably from 2 to 1 Å, and includes ethylene. , 1-propenyl, 2-propenyl, i-butenyl, 2-butenyl, 3-butenyl, 2-mercaptobut-2-enyl, etc.; "(C2-C3〇) alkyne And a linear or branched alkynyl group having 2 to 30 carbon atoms, wherein the number of carbon atoms is preferably 2 to 20, more preferably 2 to 1 Å, and includes ethynyl group, 1-propyne , 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.; "(C1-C30) alkoxy" has i a linear or branched alkane group of up to 3 carbon atoms, wherein the number of 'carbon atoms is preferably from 1 to 20, more preferably from 1 to 10 And includes methoxy, ethoxy, propoxy, isopropoxy, 1-ethylpropoxy, etc.; r(C3_C3〇)cycloalkyl" is a single ring having 3 to 30 carbon atoms Or a polycyclic hydrocarbon group, wherein the number of carbon atoms is preferably from 3 to 20, more preferably from 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.; "(C6_C3〇) ring extension "house-based" is a group formed by removing one hydrogen from a ring-burning group having 6 to 30, preferably 6 to 2, more preferably 6 or 7 carbon atoms; and, The 5- to 7-membered heterocyclic group has a group selected from the group consisting of B, N, 〇, s, p(=〇), ^ and p, and at least one hetero atom is preferably N, 〇 and S, and has 5 Up to 7% of the skeleton atoms of the ring courtyard 'and including tetrahydro Duffan " , thiolan, tetrahydropyran, etc.; "(C6_C3〇) (extension) aryl" is derived from 95566 7 201249960 aromatic hydrocarbon derived from 6 to 30 carbon atoms. a ring wherein the number of carbon atoms is preferably from 6 to 20, more preferably from 6 to 12, and includes a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a fluorenyl group. , mercapto, triphenyl, ketone, tetracenyl, sulfhydryl, chrysenyl, naphthacenyl, fluoranthenyl, and the like. Further, '3 to 30 members (extended) heteroaryl group) has at least one, preferably 1 to 4, selected from the group consisting of B, N, 0, S, P (=0), Si and P. a hetero atom of the group and an aryl group of 3 to 30 ring skeleton atoms; which is a monocyclic ring or a fused ring fused to at least one benzene ring; preferably 5 to 21, more preferably 5 Up to 12 ring skeleton atoms; may be partially saturated; may be formed by linking at least one heteroaryl or aryl group to a heteroaryl group via one or more single bonds; and, including monocyclic heteroaryls Base, including sulphate, septyl, °, p, sulphate, η, thiol, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, carbazolyl, Ordinary dimercapto, triterpene, tetraterpenoid, trisyl, tetra-beta, sulfhydryl, pyridyl, pyridyl, pyrimidinyl, hydrazine, etc., and fused ring heteroaryl , including benzofuranyl, benzothiophene, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benziso-saltyl, benzo Heteroquinone Group, isobutyl, [pi] yl flower flowers ,, υ group.丨嗤 丨嗤, benzo-dithiol, wahrine, isolinyl, cinnolinyl, quinazolinyl, quinoxaline, carbazolyl, phenyl phenyl, morphine Base, benzodioxoiyl and the like. "Halogen" includes F, Cl, Br and I. As used herein, the term "substituted" as used in "unsubstituted or unsubstituted" means that a hydrogen atom of a particular functional group is replaced by another atom or radical (i.e., a substituent). And the substituted (extended) alkyl group in the group of L2, Ri to Rig and the core to R27, the substituted alkenyl group, the substituted alkynyl group; a substituted cycloalkyl group, the substituted heterocyclic ring, the substituted (extended) aryl group, the substituted (extended) heteroaryl group, and the substituent on the aromatic ring of the generation are individually selected independently At least one of the group consisting of: hydrazine, halogen, halogen-substituted or unsubstituted (cl_C3 〇) alkyl, (C6-C30) aryl, substituted by (C6-C30) aryl or not Substituted to 30-membered heteroaryl, (C3-C30) cycloalkyl, 5- to 7-membered heterozygous, (C1-C30)alkyldecyl (&11^13丨171), ( [6 gas 30) aryl decyl, (C1-C30) alkyl (C6-C30) aryl decyl, (C2_C3 fluorene) dilute (C2-C30) alkynyl, cyano, carbazolyl, C1-C30)alkylamino group, (C6_C3〇) aryl Fee group, (C1-C30)alkyl (C6-C30) arylamine group, (C6-C30) aryl boron Ik group, (C1-C30 ) calcinyl group, (C1-C30) alkyl (C6-C30) ^• base steryl group, (C6-C30) aryl (C1-C30) alkyl group, (C1-C30 Carboxyl (C6-C30) aryl, carbonyl, carboxyl, nitro and hydroxy groups. In the above formula 1, it is preferred that b is independently a single bond, a substituted or unsubstituted 5 member to 21 member heteroaryl group, a substituted or unsubstituted (C6-C20) extended aryl group, Or substituted or unsubstituted (C6_C2〇) Cyclo-aryl aryl is more preferably selected from one of the following groups: single bond, extended base, extended base, extended phenyl, extended triphenyl Terphenylene, thiol, andenylene, thiophene, phenanthrene, triphenylenylene, phenylenylene, chrysenylene, naphthasenylene, Propadiene 95566 9 201249960 fluorantenyl, hexanyl, thienyl, pyridyl, imidazolium, pyrazolyl, thiazolyl, thiadiazole, sigh Base, exoisoxazole group, exocarbazole group, exfoliation f oxadiazole group, extensin trisyl group, four cultivating base, triazolyl group, tetrazolyl group, exofuranyl group, exopyridine group, exfoliation Base, extension of pyridine group, hydrazine, benzofuranyl, benzophenanthene, benzofuranyl, benzoimidazolyl, benzene And thiazino, benzoisothiazolyl, benzoxazole, stupid and carbazolyl, exo- hydrazino, hydrazino, carbazolyl, benzothiadiazole Basis, 啥 啥 基 基 , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , Benzodioxolylene, dibenzofuranyl and dibenzothiophenyl. In the above formula 1, Y] and 丫2 are each independently represented by -〇-, -S-, -cr8R or -NRm-', wherein 'Re and 匕 are preferably independently substituted or unsubstituted ( Cl-C30)alkyl or substituted or unsubstituted (C6-C30) aryl; or Rs and R9 each via substituted or unsubstituted (C3-C30) alkyl or (C3-C30) The alkenyl chain is bonded to an adjacent substituent to form a monocyclic or polycyclic alicyclic or aromatic ring, and more preferably independently represents an unsubstituted (c bcl〇) danthyl group or an unsubstituted group (C6 -C12) aryl, or linked to adjacent substituents to form a monocyclic or polycyclic (C1-C10) alicyclic or (C6-C15) aromatic ring. And, "preferably means a substituted or unsubstituted (C6_C3〇) aryl group or a substituted or unsubstituted 3 to 30 membered heteroaryl group, more preferably an or not; 11- (C1-C6) aryl or (C6-C12) aryl substituted (C6-C20) aryl, or substituted by (C6-C12) aryl from 5 to 21 membered heteroaryl. 95566 10 201249960 In the formula 1, '匕 to R7 are preferably independently represented by hydrogen, substituted or unsubstituted (C6-C30) aryl or -SiR^M25, or via substituted or unsubstituted (C3-C30) stretching. An alkyl group or a (C3-C30) chain extending to an adjacent substituent to form a monocyclic or polycyclic alicyclic or aromatic ring, more preferably independently hydrogen, unsubstituted (C6-C12 An aryl group or -SiR23R24R25, or linked to an adjacent substituent to form a monocyclic or polycyclic (C6-C12) aromatic ring.

In the above formula 1, it is selected from the following structures, but is not limited thereto:

Representative compounds of the invention include the following compounds: 95566 11 201249960

95566 12 201249960

95566 13 201249960

95566 14 201249960

The compound of the sub-material can be prepared according to the following (4) for the organic electrorheological reaction formula. [Reaction formula]

Furthermore, the present invention provides an organic electric field illuminating device comprising a compound of formula i. The organic electric field light-emitting device includes a first electrode, a second electrode, and at least one organic layer interposed between the first electrode and the second electrode. The organic layer comprises at least one hydrazine compound according to the invention. Further, the organic layer contains a light-emitting layer containing the compound of the formula 1 as a host material. Further, the dishing agent used in the organic electroluminescence device in combination with the host material according to the present invention may be selected from the compounds represented by the following formula 2:

MlL10V0V03 --------------------- (2) where Μ1 is selected from the group consisting of Ir, Pt, Pd and Os; Lm, 95566 15 201249960 L1D2 and The Lm series are individually selected from the following structures:

R2〇1 to R2D3 are each independently represented by hydrogen, deuterium, substituted or unsubstituted (C1-C30)alkyl by one or more halogens, substituted or unsubstituted by one or more (C1-C30) alkyl groups. (C6-C30) aryl, or _ s; s. 2 〇 4 to Rm each independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted ( C1-C30) alkoxy, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30 Aryl, substituted or unsubstituted mono(C1~C30)alkylamino, substituted or unsubstituted bis(C1-C30)alkylamino, substituted or unsubstituted, 95566 16 201249960 Mono(C6-C30)arylamino, substituted or unsubstituted bis(C6-C30)arylamino, SF5, substituted or unsubstituted tris(CbC30)alkyldecyl, by Substituted or unsubstituted bis(Cl-C30)alkyl (C6-C30) aryl carbyl, substituted or unsubstituted tris(C6-C30) arylalkyl, cyano or halogen; R22. To R223, each independently represents hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted with one or more alkyl groups (C6-C30) Aryl; 224 and R225 independently represent hydrogen, gas, substituted or unsubstituted (n-C30) alkyl, substituted or unsubstituted (C6_C3〇) aryl, or halogen 'or 1^ 4 and R225 may be linked to each other by a (C3_C12) alkylene group or a (C3-C12)alkylene group having a fused ring to form a monocyclic or polycyclic alicyclic or aromatic ring; R226 Is a substituted or unsubstituted (C1-C30) alkyl group, a substituted or unsubstituted (C6-C30) aryl group, a substituted or unsubstituted 5 member or 30 Å, or Halogen; to R229 are each independently represented by hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl or halogen; R23^R232 is represented by Only 2 into 236 or R 239 ft. 240; R231 to R242 are each independently represented by hydrogen, gas, substituted or unsubstituted (C1-C30) alkyl, (Ci_c3〇) alkoxy, toothed by one or more dentants Prime Substituted or not taken 95566 17 201249960 (C6-C30)^r, yl, or substituted or unsubstituted (c5_c3〇) cycloalkyl, or to R242 may be individually extended via (C2_C3〇) An alkyl group or (C2-C30)alkylene chain to an adjacent substituent to form a spiro or fused ring, or may be extended via an alkyl group or a (C2-C30) alkyl group. Junction to Rm or Rm to form a saturated or unsaturated fused ring. The dopant of Formula 2 includes the following, but is not limited thereto:

<1

95566 201249960

The organic electroluminescence device according to the present invention may further comprise, in addition to the compound represented by Formula 1, at least one compound selected from the group consisting of an arylamine compound and a styrene arylamine compound. In the organic electric field light-emitting device according to the present invention, the organic layer may further comprise at least one metal selected from the group consisting of a metal of Group 1 of the periodic table, a metal of Group 2, and a transition metal of the fourth cycle. , a transition metal of the fifth cycle, an organometallic of a lanthanide metal and a d-transition element, or at least one complex compound containing the metal. The organic layer may include a light emitting layer and a charge generating layer. The electric field light-emitting device according to the present invention emits white light by including at least one light-emitting layer containing a blue electric field light-emitting compound, a red electric field light-emitting compound or a green electric field light-emitting compound in addition to the organic layer containing the compound according to the present invention. In the organic electroluminescence device according to the present invention, at least one layer (hereinafter referred to as "surface layer") is preferably selected from the group consisting of a chalcogenide layer, a metal halide layer and a metal oxide layer. The body is disposed on one or more inner surfaces of one or both of the electrodes. Specifically, it is preferable to provide a layer of a cerium element compound (including an oxide) of Shi Xi or Ming on the anode surface of the electric field luminescent medium layer, and to provide a metal halide layer or a metal oxide layer on the EL medium layer. On the surface of the cathode. This surface layer 95566 19 201249960 provides operational stability to the organic electric field illuminating device. Preferably, the chalcogenide compound comprises Si〇x (l^x^2), Al〇x (lgx$15),

SiAlON 4, the metal halide includes LiF, MgF2, a fluoride of a rare earth metal, and the like; and the metal oxide includes Cs2〇, Li2〇, Mg〇, SrO, BaO, CaO, and the like. In the organic electric field light-emitting device according to the present invention, it is preferable that at least a mixed region of the electron transporting compound and the reducing dopant or a mixed region of the hole transporting compound and the oxidizing dopant is disposed on the pair of electrodes. On a surface. In this case, the electron transporting compound is reduced to an anion, and thus it becomes easier to inject and transport electrons from the mixed region to the electric field illuminating medium. Furthermore, the hole transporting compound is oxidized to form a cation, and thus it becomes easier to inject and transport the electric/synthesis region to the electric field illuminating medium. Preferably, the oxidizing dopant comprises various Lewis acids and acceptor compounds; the reducing dopants include alkalis, genus, alkali metal compounds, alkaline earth metals, rare earth metals and mixtures thereof . A reducing dopant layer may be employed as the charge generating layer to prepare an electric field light-emitting device having two or more layers of an electric field light-emitting layer and emitting white light. Hereinafter, the compound for an organic electronic material, the method for producing the compound, and the luminescent property of the device comprising the same according to the present invention will be explained in detail with reference to the following examples. Preparation Example 1: Preparation of Compound C-2 95566 20 201249960

Preparation of Compound C11 9-Phenyl-9H-indazol-3-ylboronic acid (14 g (g), 48.76 mmol (mmol)), 3-Day _911-〇卡嗤 (10 g, 40.63 mmol) K2CO3 (13.5 g, 97.52 mmol) and Pd(PPh3)4 (2.35 g, 2.03 mmol) were added to a mixture of 200 ml (mL) of toluene, 50 mL of EtOH and 50 mL of purified water. After the reaction mixture was stirred at 90 to 100 ° C for 3 hours, the mixture was cooled to room temperature. The aqueous layer is removed from the mixture by gravity separation. The obtained organic layer was concentrated, triturated with dichloromethane (MC), and then filtered to afford Compound C-1 (12 g, 72%). Preparation of compound C-1-2 2,4-dioxaquinazoline (30 g, 151 mmol), 9-phenyl-9H-carbazole~3-boronic acid d5.6 g, 75.3 mmol), P ( After i(PPh3)4 (2.6g, 2.3 gurry 1) and Na2C〇3 (i6 g, 150 mmol) were dissolved in a mixture of toluene (300 mL) and distilled water (75 mL), the reaction mixture was (10) It agitates 2 to obtain the organic layer obtained by steaming under reduced ink, and then grinds with MeOH. = The solid is dissolved in MC, passed through 7 gel, and then ground with H1 to obtain compound Cl-2. (9.3g, 51.4%) Preparation of Compound C-2 Compound C~l-1 (5.3 g, 14.7 mmol) and compound c-1-2 •4S' 15·8_ο1) were suspended in diterpene After guanamine (MF) 8 () mL, 95566 21 201249960 60 ° / 〇 NaH (948 mg (mg), 22 mmol) was added to the mixture at room temperature. The resulting reaction mixture was stirred for 12 hours. After adding purified water (1 liter (l)), the mixture was filtered under reduced pressure. The obtained solid was triturated with ethyl acetate, dissolved in MC, filtered through silica gel, and then triturated with MC/n-hexane to obtain Compound C-2 (1.9 g, 16.8%). The MS/FAB measurement was 778; the calculated value was 777. 91 Preparation 2: Preparation of Compound C-13

Preparation of Compound C-2-1 2,4-Dioxaquinazoline (50 g, 251 mmol) and dibenzo[b,d]furan-4-ylboronic acid (53.2 g, 251 mmol) were dissolved in hydrazine. After a mixture of benzene (1 l) and water (200 mL), hydrazine (triphenylphosphine) palladium (14.5 g, 12.5 mmol) and sodium carbonate (8 〇g, 755 mmol) were added. In the reaction mixture. The reaction mixture was stirred at 80 ° C for 20 hours and cooled to room temperature. After the reaction was quenched with 200 mL of chlorinated aqueous solution, the mixture was extracted with ethyl acetate 1 [yield, and the aqueous layer was further extracted with 1 L of dichloromethane. The organic layer was dried over anhydrous magnesium sulfate and removed under reduced pressure. The solid obtained was filtered through silica gel and the solvent was removed under reduced pressure. The obtained solid was washed with 1 mL of ethyl acetate (EtOAc) to afford Compound C-2-l (50 g, 74%). Preparation of Compound C-13 After dissolving Compound C-1-1 (50 g, 122 mmol) in DMF, 60% NaH (5.9 g, 148 mmol) was slowly added to the reaction mixture. 95566 22 201249960 After the reaction mixture was stirred at room temperature for 1 hour, compound C 2 -K 51 g, 147 mmol) was added to the reaction mixture. The reaction mixture was stirred at room temperature for 20 hours. Ice water was slowly added dropwise to the reaction mixture to terminate the reaction. The reaction mixture was then taken care of to yield the solid formed. The resulting solid was washed with 1 L of water and then washed with MeOH 1L. The resulting solid was dried, dissolved in CHCldL and filtered through a silica gel to remove inorganic material. The solvent in the resulting solution was removed to obtain a solid. The obtained solid was recrystallized from DMF to give Compound C-13 (50 g, 58). MS/FAB: 703. calc. 702. 80 Preparation Example 3: Preparation of Compound C-14 B (〇H) 2 03⁄4

C-3-1

Preparation of compound C-3-1 2,4-dioxaquinazoline (5〇8,251111111〇1) and dibenzo-[^,(1] thiophen-4-ylboronic acid (57.3 g, 251 mmol) After dissolving in a mixture of toluene (1 L) and water (200 mL), hydrazine (triphenylphosphine) (14. 5 g, 12.5 mmol) and sodium carbonate (80 g, 755 mmol) were added. In the reaction mixture, the reaction mixture was stirred at 80 ° C for 20 hours, and cooled to room temperature. After quenching with 200 ml of aqueous ammonium chloride solution, the reaction mixture was extracted with 1 L of ethyl acetate, and water was further extracted with dioxane 1 L. The organic layer was dried over anhydrous MgSO.sub. 3-l (50g, 60%). 95566 23 201249960 Preparation of Compound C-14 After compound C11 (50 g, 122 mmol) was dissolved in DMF, 60% NaH (5.9 g, 148 mmol) was slowly added. In the reaction mixture, after the reaction mixture was stirred at room temperature for 1 hour, compound C-3-1 (51 g, 147 mmol) was added to the reaction mixture. The mixture was stirred at room temperature for 20 hours, and ice water was slowly added dropwise to the reaction mixture to terminate the reaction. Subsequently, the reaction mixture was filtered to obtain a solid which was formed. The obtained solid was washed with 1 L of water, followed by washing with MeOH 1 L. The obtained solid was dissolved in CHCh 4L and filtered through a silica gel to remove the inorganic substance. The solvent in the obtained solution was removed to obtain a solid. The obtained solid was recrystallized from DMF to obtain Compound C-14 (50 g, 57%) The MS/FAB measurement was 729; the calculated value was 718. 87 Preparation 4: Preparation of Compound C-20

Preparation of Compound C-4-1 Dibenzo[b,d]furan-4-yl succinic acid (19 g, 89.6 mmol), bromobenzene (18.4 mL, 138 mmol), Pd(PPh3)4 (2.9 g , 2.5 mmol) and Na2C〇3 (23.2 g, 219 mmol) were dissolved in a mixture of toluene (375 mL), EtOH (75 mL) and distilled water (75 mL). Stir at °C for 4 hours. The obtained organic layer was distilled under reduced pressure, and then filtered through a column of MC and hexane to obtain compound C-4-K17 g, 77%). 95566 24 201249960 Preparation of compound C-4-2 After dissolving the s material C-4~1 (17 g, 65.3 mmol) in tetrahydrofuran (THF) (5Q () mL), at -78 ° C A 2. 5M n-butyl chain (n-BuLi) in hexane cold (52.2 mL, 130 mmol) was added to the mixture and mixture was stirred for 1 hour. The reaction mixture was stirred for 2 hours while B (0i Pr) 3 (21.8 mL, 195 mm Ql) was slowly added to the reaction mixture to add 2 M HCl, and the reaction mixture was quenched to extract water and EA. Reacts this cockroach. The solid obtained was recrystallized from hexane to obtain Compound C-4-2 (6.4 g, 33°/.). Compound (^4-3) will be prepared as compound C-4~2 (4.9 g, 24.4 with 〇1), 2,4-dichloroquinazoline (6·4 S, 22.2 mnml), Pd(PPh3)4 (11 g, 2 5 颜(4) and MO^7·1 g' 66.6 咖. 1) Dissolved in a solution of stupid (30G mL) and distilled water (75 after the reaction mixture was given in the 9th generation for 2 hours) The organic layer obtained by reduction under reduced pressure was then ground with MeQH. The solution of the capsule was solved in mc and passed through; the gel transition, followed by grinding with MC and the same to obtain compound C-4-3 (4.1 g, 45%) Preparation of β compound C-20 After compound C+3 (4.5 g, 10.9 mraQl) and compound ch (4.1 g, 9, 9 mmol) were suspended in DMF 80 mL, 6 at room temperature 〇% Ν&Η «Μ mg, 14. 8 mmol) was added to the mixture. The resulting reaction mixture was stirred for 12 hours. After adding purified water (1 L), the mixture was filtered under reduced pressure. /Ethyl acetate was ground together' and then ground with DMF, followed by grinding with EA/THF. The obtained solid was dissolved in MC, 95566 25 201249960 was filtered through a gelatinous gel, followed by grinding with MeOH/EA to obtain compound C. -20 (3. 4 g, 44 %) The MS/FAB measurement was 779; the calculated value was 778. 9 制备 Preparation 5 · Preparation of Compound C-21

Preparation of compound C-5-1 will be dibenzo[b,d]-indol-4-ylfolic acid (2〇g, 87 7 curry 1), desert benzene (18.4H1L, 175_l), Pd (PPh3) 4(2 9g, 2 5_υ and Na2C〇3 (23.2 g, 219 mmol) were dissolved in a mixture of toluene (375 mL), EtH (75 mL) and distilled water (75 mL). The mixture was stirred for 4 hours. The obtained organic layer was evaporated under reduced pressure, and then filtered through a column of MC and hexane to obtain compound 〇5_1 (17 g, 75%). Preparation of Compound C-5-2 Compound C- 5-1 (17 g, 65. 3 mmol) was dissolved in THF (500 mL). A solution of 2.5 Mn-BuLi in hexane (52.2 mL, 130 〇1) was added to the reaction at -78 °C. In the mixture, the reaction mixture was stirred for 1 hour. The reaction mixture was stirred for 2 hours while B (0i-Pr) 3 (21.8 mL, 195 mmol) was slowly added to the reaction mixture. After the 2M HCl was quenched, The reaction mixture was extracted with distilled water and EA. The obtained solid was recrystallized from MC and hexane to afford compound C-5-2 (11.5 g, 60%). Preparation of Compound C-5-3 95566 26 201249960 Compound c_5_2 ( 8. 3 g, 41.5 ship)), , *-dichloroquinazoline (11. 5 g' 37. 8 mmol), Pd (PPh3) 4 (2.2 g, 2.5 mmol) and ^2〇) 3 (12 g' il3匪〇1) After dissolving in this mixture of toluene (3 〇〇mL) and distilled water (75%), the reaction mixture was stirred at 9 (TC for 2 hours. The organic layer was obtained by distillation under reduced pressure, followed by MeOH. Grinding was carried out. The obtained solid was dissolved in MC and filtered through a silica gel, followed by grinding with MC and hexane to obtain Compound 05-3 (10 g, 68%). Preparation of Compound C-21

After compound C-5-3 (5 g, 11.8 mmol) and compound C-1-1 (4.8 δ' 11. & mmol) were suspended in DMF 80 mL, 60% NaH mg at room temperature , 22 mmol) was added to the mixture. The resulting reaction mixture was stirred for 12 hours. After adding purified water uL), the mixture was filtered under reduced pressure. The resulting solid was triturated with MeOH / ethyl acetate then triturated with DMF and then triturated with EA / THF. The obtained solid was dissolved in MC, filtered through silica gel, and then triturated with MeOH/EA to afford compound c- 21 (4.8 g, 51%). MS/FAB measurement was 795; calculated 794. 96 Preparation 6: Preparation of compound C-33

Preparation of Compound C-6-1 95566 27 201249960 A benzo[b,d]n-fol-4-yl succinic acid (20 g, 94.34 mmol), bromo-4-moth-benzene (53) 4 ml, 188. 68 mmol), Pd(PPh3)4 (5. 45 g, 4.72 mmol) and K2C〇3 (39, lg, 283.1 mmol) dissolved in toluene (900 mL), EtOH (200 mL) After distilling the mixture of crane water (2 〇〇 mL), the reaction mixture was stirred at 70 to 8 (TC for 3 hours. After the reaction was terminated, the aqueous layer was removed from the mixture by gravity separation. Subsequently, the obtained organic layer was obtained. Concentrate and purify through a column to obtain compound C-6-1 (17 g, 56%). Preparation of Compound C-6-2 Compound C-6-1 (17 g, 52.6 mmol) was dissolved in THF (After 400 1111 Torr, 2.5 liters of 11-3111 hexane solution (31.5 1111, 78. 9 mmol) was added to the reaction mixture at _78 Torr, and the reaction mixture was stirred for 1 hour. The reaction mixture was stirred for 12 hours. At the same time, wB(〇i_Pr)3 (24.丨ml, 10 5. 2 imo 1) was added to the reaction mixture. After the reaction was terminated, 20 mL of purified water was slowly added to the reaction mixture to ea/nh4C1. The aqueous mixture is drawn to the reaction mixture. The organic layer was obtained by trituration with MC/hexane, followed by filtration to obtain Compound C-6-2 5 g 96%). Preparation of Compound C-6-3

Compound 06-2 (4.5 g, 50.33 mmol), 2, 4-dioxapyrene (11.5 g, 50.33 nin, ol)^Na2C〇3 (20.9 g, 150.99 mmol) and Pd (PPh3) 4(2. 9 g, 2· 52 πιιηοΐ) dissolved in 曱 ( (go.), Et 〇 H (75 mL) and steamed water (75 mL) in /3⁄4 compound, after 75 to mix The reaction mixture was subjected to a reaction of 12 m after the reaction of the reaction mixture to a room temperature to remove the aqueous layer from the mixture by gravity separation. The resulting organic layer was concentrated, triturated with THF / MeOH - filtered, then dried. The dried compound of 95566 28 201249960 was dissolved in 3 L of chloroform and filtered through silica gel. The remaining solution was concentrated and triturated with EA to give compound C-6-3 (3.8 g, 19%). Preparation of Compound C-33 After compound 8 g, 9.34 mmol) and compound C-6-3 (3.8 g, 9.34 mmol) were suspended in DMF 80 mL, 60% NaH (l· at room temperature) 12 g, 28.02 mL) was added to the mixture. The resulting reaction mixture was stirred for 12 hours. After adding purified water (il), the mixture was filtered under reduced pressure. The resulting solid was triturated with Me〇H/ethyl acetate, then triturated with DMF and then triturated with EA/THF. The obtained solid was dissolved in MC to be filtered through EtOAc, and then triturated with MeOH/EA to obtain Compound C-33 (2.9 g, 40%). MS/FAB measured 779; calculated 778. 90 Preparation 7: Preparation of compound C-34

Preparation of Compound C-7-1

In a 2000 mL round bottom flask, bromo-4-iodo-stupid (49.6 g, 〇17 mol), dibenzo[b,d]thiophen-4-ylboronic acid (20 g, 0.087 mol), Pd (PPh3) 4 (5. 0 g, 〇. 044 mol) and Na2C〇3 (18. 5 g, 0. 18 mol) after the mixture of benzene (880 mL) and h2 〇 (200 mL), The reaction mixture was searched at 80 ° C for 12 hours. After the reaction was terminated, the reaction mixture was extracted with ethyl acetate 95566 29 2012499. Subsequently, the resulting organic layer was dried with MgS 4 and filtered. The solvent was removed from the organic layer under reduced pressure, and the organic layer was filtered through a column to obtain white solid compound C-7-1 (21.2 g, 71%). Preparation of Compound C-7-2 After compound 07-1 (21.4 g, 〇.〇6 mol) and dry THF (1000 mL) were placed in a 2000 mL round bottom flask under anhydrous conditions, at _78 ° C A n-BuLi hexane solution (37 mL, 2.25 hydrazine solution) was slowly added to the reaction mixture while stirring the mixture under a nitrogen atmosphere. The reaction mixture was stirred at -78 °C for 1 hour. After B (0i_PrM29 mL, 0.13 mol) was slowly added to the reaction mixture at -78 °C, the reaction mixture was heated to room temperature and reacted for 12 hours. After the reaction was terminated, the reaction mixture was extracted with ethyl acetate. Subsequently, the resulting organic layer was dried with MgS 4 and filtered. After removing the solvent from the organic layer under reduced pressure, the organic layer was filtered through column to afford white solid compound C-7-2 (15. 5 g, 81%). Preparation of compound C-7-3 in a 250 mL round bottom flask, compound C-7-2 (15.5 g, 0.051 111 〇1), 2,4-dichloroquinazoline (12.2 舀, 0.06) 111〇1), Xian 2(:03 (16.2 g, 0.153 mol) and Pd(PPh3)4 (2·94 g, 0.0025 mol) were added toluene (250 mL), EtOH (40 mL) and H2 (70 mL) After the mixture was stirred, the reaction mixture was stirred at 80 ° C for 12 hours. After the reaction was terminated, the reaction mixture was extracted with ethyl acetate. Then the organic layer was dried with MgSO 4 and filtered. After removal of the solvent, the obtained solid was recrystallized to give compound 07-3 (14 g, 65%). Preparation of Compound C-34 95566 30 201249960 NaH 60% (0. 62 g, 〇. 0154 mol) under anhydrous conditions The mixture was placed in a 250 mL round bottom flask with DMF (60 mL). After the compound Cl-1 (4.83 g, 0. 012 mol) was dissolved in DMF (3G mL), the mixture was placed in the round bottom flask. The reaction mixture was stirred for 1 hour. After compound c_7_3 (5 g, 0.012 mol) was dissolved in DMF (30 mL), the mixture was placed in the round bottom flask. After stirring the mixture for 12 hours, the yellow solid was filtered. Trituration, trituration with THF, followed by trituration to obtain compound C-34 (4.2 g, 45%). MS/FAB measured 795. Calculated value 794. 96 Preparation Example 8 · Compound C-36 Preparation

Dibenzo[b,d]°fusin-4-yl benzoic acid (20 g, 94.34 mmol), 1,3-dibromobenzene (22.3 light, 94.34 _〇1), ? (1(??113)4(5.45 transport, 4.72 mmol) and K2C〇3 (39·1 g,283.01 mmol) dissolved in toluene (8〇〇mL), EtOH (200 mL) and steamed water (200 mL) After the mixture was stirred, the reaction mixture was stirred at 70 to 80 ° C for 3 hours. After the reaction was terminated, the aqueous layer was removed from the mixture by gravity separation. Subsequently, the obtained organic layer was concentrated and purified through a silica gel column. Compound C-8-K13 g, 43%) was obtained. Preparation of Compound C-8-2 95566 31 201249960 After dissolving Compound 08-1 (13 g, 40.23 mmol) in THF (300 mL), 2.5 M n-BuLi in hexanes at -78 ° C (19 ml, 48.27 mmol) was added to the reaction mixture and the mixture was stirred for one hour. The reaction mixture was stirred for 12 hours while B (〇i-pr) 3 (13.9 raL, 60.34 ramol) was slowly added to the reaction mixture. After the reaction was terminated, 20 mL of purified water was slowly added dropwise to the reaction mixture. The reaction mixture was extracted with an ea/nh4C1 aqueous solution. The obtained organic layer was concentrated, triturated with hexane, and then purified to afford compound C-8-2 (6. 8 g, 58. 7. Preparation of compound C-8-3 Compound C-8-2 (6. 8 g, 23.6 mmol, 2, 4-dichloroquinazoline (5.38 g, 23.6 mmol), Na2C〇3 (9.8 g, 70.8 mmol) & Pd(PPh3)4 (1.36 g, 1.18 mmol) After dissolving in a mixture of toluene (24 〇mL) and distilled water (5 〇), the reaction mixture was stirred at 90 to 1003⁄4 for 12 hours. After the reaction was terminated, the reaction mixture was cooled to room temperature and separated by gravity. 4 The aqueous layer was removed from the mixture. The obtained organic layer was concentrated, triturated with THF/Me EtOAc, filtered, and then dried. The dried compound was dissolved in chloroform 3 L· and filtered through silica gel. /MeOH - trituration to obtain compound C-8-3 (3.8 g, 40%). Preparation of compound C-36 Compound C-1-1 (3.8 g, 9.34 mmol) and compound c-8-3 ( 3· 8 g' 9. 34 mmol) after suspension in DMF 80 mL, at room temperature

NaH (1·12 g, 28.02 mL) was added to the mixture. The resulting reaction was stirred for 12 hours. After adding purified water (丨L), the mixture was filtered under reduced pressure. The resulting solid was triturated with EtOAc / EtOAc (EtOAc)EtOAc. MS/FAB measured 779; calculated 778. 90 Preparation 9: Preparation of compound C-37

In a 2000 mL round bottom flask, 1,3-dioxabenzene (16.5 g, 0.2 mol), dibenzo[b, d]D-cephen-4-yl acid (15 g, 0.06) Mol), Pd(PPh3)4 (3.8 g, 0.003 mol) and Na2C〇3 (14 g, 0.13 mol) dissolved in a mixture of toluene (330 mL) and H2 (70 mL) at 80 ° C The reaction mixture was stirred for 12 hours. After the reaction was terminated, the reaction mixture was extracted with ethyl acetate. Subsequently, the resulting organic layer was dried at 1^8 〇4 and filtered. After removing the solvent from the organic layer under reduced pressure, the organic layer was filtered through a column to afford white solid compound C-9-1 (8.4 g, 40%). Preparation of Compound C-9-2 After compound C-9-1 (8.4 g, 0.025 mol) and dry THF (200 mL) were placed in a 500 mL round bottom flask under anhydrous conditions, n at -78 ° C A solution of -BuLi hexane (15 mL, 2.25 hydrazine solution) was slowly added to the reaction mixture while stirring the mixture under a nitrogen atmosphere. The reaction mixture was stirred at -78 ° C for 1 hour. After B (0i-Pr) 3 (11.4 mL, 0.05 mol) 95566 33 201249960 was slowly added to the reaction mixture at -78 ° C, the reaction mixture was heated to room temperature and reacted for 12 hours. After the reaction was terminated, the reaction mixture was extracted with ethyl acetate. The resulting organic layer was then dried with MgS 4 and filtered. After removing the solvent from the organic layer under reduced pressure, the organic layer was filtered through a column to obtain a white solid compound C-9-2 (6 g, 80%). Preparation of Compound C-9-3

In a 250 mL round bottom flask, compound c-9-2 (5.9 g, 0.02 mol), 2,4-dioxaquinazoline (4.6 g, 0.02 mol), Na2C〇 3 (6·2 g, 0.058 mol) and Pd(PPh3)4 (ll g, 0.00097 m〇i) were added to a mixture of toluene (100 mL), EtOH (14 mL) and H2 (30 mL) at 70°. C The reaction mixture was stirred for 3 hours. After the reaction was terminated, the reaction mixture was extracted with ethyl acetate. The resulting organic layer was then dried with MgS 4 and filtered. After the solvent was removed from the organic layer, the organic layer was filtered through a column to afford compound C-9-3 (7.0 g, 85%). Preparation of Compound C-37 NaH 60% (0.5 g, 0.013 mol) and DMF (40 mL) were placed in a 250 mL round bottom flask under anhydrous conditions. After dissolving the compound 7 g, 〇 '009 mol, in DMF (30 mL), the mixture was placed in the round bottom flask. The reaction mixture was stirred for 1 hour. After dissolving Compound C_9_3 (4 g, 0. G095 mol) in DMF (3 mL), the mixture was placed in the round bottom flask. After the mixture was stirred for 12 hours, a yellow solid was filtered, washed with MeOH, EtOAc EtOAc (EtOAc) MS/FAB measurement was 795; calculated 794. 96 95566 34 201249960 Preparation 10: Preparation of compound C-39

Preparation of Compound C-10-1 Compound C-1-1 (14 2,34. 3 〇1) and 1-bromo-4-iodobenzene (48.5 g, 171.4 molol) 'CuI (3. 3 g, 17. 1 mmol) 'K3P〇4 (21. 8 g, 102.9 mmol) and ethylenediamine (EDA) (2,3 mL, 34.3 mmol) in benzene (500 mL) After the middle, the reaction mixture was stirred under reflux for 1 day? The reaction mixture was extracted with EtOAc, EtOAc (EtOAc m.) The preparation of the compound C-10-2, after dissolving the compound C-10-l (15. 5 g, 27.5 mmol) in THF (250 mL), at -78 ° C, 2. 5 M n-BuLi A hexane solution (17.6 mL, 44 mmol) was added to the reaction mixture and the mixture was stirred for 1 hour. The reaction mixture was stirred for 2 hours while B (〇i-Pr) 3 (12.6 raL, 55 mmol) was slowly added to the reaction mixture. After the 2M HCl purged mixture was added, the reaction mixture was extracted with distilled water and EA. The obtained solid was recrystallized from MC and hexane to obtain Compound C-10-2 (8.7 g, 60%). Preparation of Compound C-39 The compound 〇3_l (3.2 g, 9.2 fine 1〇1), compound C-10-2 (4.9 g, 9.2 mmol), Pd(PPh3)4 (532 mg, 〇.46minol ) &Na2C〇3 (2.9 g, 27·6 mmol) was dissolved in a mixture of toluene (55 mL), Et0H (14 mL) and 95566 35 201249960 distilled water (14 mL). . The reaction mixture was extracted with EtOAc (EtOAc) EtOAc (EtOAc). MS/FAB measured 795; calculated 794. 96 Preparation 11: Preparation of compound C-40

Preparation of Compound C-40 Compound C-2-1 (3.2 g, 9.2 mmol), Compound C-10-2 (4.9 g, 9.2 mmol), Pd(PPh3)4 (532 mg, 0.46 mmol) & NazC〇3 (2.9 g, 27.6 _ol) was dissolved in a mixture of EtOAc (EtOAc) (EtOAc) (EtOAc) The reaction mixture was extracted with distilled water and EA, and then filtered, and then filtered through silica gel to afford compound C-40 (5.5 g, 75%). The MS/FAB measurement was 779; the calculated value was 778. 90. Example 1: Manufacture of an OLED device using the compound according to the present invention A ruthenium LED device was fabricated using the compound according to the present invention. Transparent electrode indium tin oxide (IT0) film (15 Q/sq) on a glass substrate for organic light-emitting diode (0LED) device using ultrasonic cleaning with trichloroethylene, acetone, ethanol and steamed crane water (Samsung Corning, Republic of Korea), then stored in isopropanol. Subsequently, the ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. Ν1-(naphthalen-2-yl)-95566 36 201249960 ,,财-双(4-(naphthalen-2-yl(phenyl)amino)phenyl)--phenylbenzene-1,4-di An amine is introduced into one of the chambers of the vacuum vapor deposition apparatus, and then the pressure of the chamber of the apparatus is controlled to 1 (Γ6 torr). Thereafter, the chamber is subjected to an electric current to volatilize the introduced material, thereby A hole injection layer having a thickness of 60 nm is formed on the substrate of ΙΤ0. Subsequently, Ν, Ν'-bis(4-biphenyl)-Ν, Ν'-bis(4-biphenyl)-4, 4 '-Diaminobiphenyl is introduced into another chamber of the vacuum vapor deposition apparatus, and is volatilized by applying a current to the chamber to form a hole transport layer having a thickness of 20 nm on the hole injection layer. Thereafter, Compound C-2 was introduced into one of the chambers of the vacuum vapor deposition apparatus as a host material, and Compound D-11 was introduced into another chamber as a dopant. The two materials were volatilized at different rates and were 4 to 20 wt. A doping amount of % is deposited to form a light-emitting layer having a thickness of 30 nm on the hole transport layer. Subsequently, 9, 10-bis(1-naphthyl)-2-(4-phenyl-1-phenyl) -1H- And [d]imidazole) is introduced into a small chamber and introduced into another chamber by 8-ionium quinolate. The two materials are volatilized at different rates and deposited at a doping amount of 30 to 70 wt%. An electron transport layer having a thickness of 30 nm is formed on the light-emitting layer. Subsequently, lithium 8-hydroxyquinolate having a thickness of 1 to 2 nm is deposited on the electron transport layer as an electron injection layer, and another vacuum gas phase is used. A deposition apparatus deposits an aluminum (A1) cathode having a thickness of 150 nm on the electron injecting layer. Thus, an OLED device is fabricated. All of the materials used to fabricate the OLED device are purified by 1 (T6 torr vacuum sublimation) The OLED device manufactured shows that when the driving voltage is 4.0 volts (V), the illuminance is 1,020 cd/m2 of red light, and the current density is 14. 0 mA/cm 2. Furthermore, for 5,000. In terms of illuminance of nit, the illuminance is reduced to the shortest faU6G hour consumed by its 95566 37 201249960 9〇%. Examples 2 to 11: making it a paste! The compound of the present invention is manufactured in an OLED device. (4) as a host material and dopant.

Comparative Example 1: Using the Younger You ya, J, and the electric field luminescent compound to manufacture the OLED device The OLED device was fabricated in the same manner as in Example 1, but by making the field 1 4' - N, N -. Above, phase ', ~carbazole-biphenyl (CBP) as a host material and compound D 11 as a dopant to deposit a light-emitting layer having a thickness of 3 Å (10) on the hole transport layer' and by using double (2) -Methyl-8-hydroxyquinoline)-4-phenylphenol aluminum (III) deposits a hole barrier layer having a thickness of 10 nm. The manufactured OLED device showed a red illuminating current density of 2 〇.〇mA/cm2 when the driving voltage was 8.2 volts (V). For the illuminance of 5,000 nit, the illuminance is reduced to 90%. The shortest time is 10 hours. Host material dopant driving voltage (V) Current density (inA/cm2) Illuminance (cd/mz) / Color illumination from 5,000 nit to 90% minimum time required C-2 D-11 4.0 14.0 1020/ Red 60 C-4 D-7 3.9 7.7 1030/Red 200 Fly-13 D-7 3.9 7.1 1050/Red 150 C-14 D-7 4.0 7.2 1090/Red 150 C-21 D-11 4.3 13.2 1010/Red 150 C-33 D-7 4.2 7.2 1040/Red 130 Fly-34 D-11 4.3 12.8 1010/Red 130 C-36 D-7 Γ4.1 7.3 "1080/Red 150 C-37 D-7 4.1 7.5 1080/Red 150 C-39 D-7 4.0 6.7 1050/Red 120 Fly-40 D-7 4.0 6.8 1070/Red 120 —CBP D-11 “8.2 20.0 1000/Red 10 95566 38 201249960 The compounds of the present invention are superior to traditional materials. Further, the device using the compound according to the present invention as a host material can increase the power efficiency by lowering the driving voltage, thereby improving power loss. [Simplified Schematic] Benefits [Main Component Symbol Description] No 95566 39

Claims (1)

201249960 VII. Patent application scope: 1. A compound represented by the following formula 1, ----------(1) wherein, Li and b are each independently represented by a single bond, substituted or unsubstituted 5 to 30 members of the heteroaryl group, substituted or unsubstituted ( C6-C30) aryl, or substituted or unsubstituted (C6-C30) cycloalkyl; Χι means CH or N; Υι and Y2 are individually independent - 〇-, -S-, -CRsR9 -or-NRi〇-; Ri to R10 are each independently represented by hydrogen, gas, statin, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl , substituted or unsubstituted, 3 to 30 membered heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted 5 to 7 membered heterocycloalkyl, Substituted or unsubstituted (C6-C30) aryl (C-C30) alkyl group, substituted or unsubstituted (C6-C30) aryl group fused to at least one (C3~C30) cycloalkyl group And 5 or 7 membered heterocyclic groups of at least one substituted or unsubstituted (C6-C30) aromatic ring, and at least one substituted or unsubstituted (C6_C30) aromatic ring (C3-C30)cycloalkyl, -nr21r22, _SiR23R24R25, 95566 1 20124 9960 -0R27, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2-C30) alkynyl, cyano, nitro, or hydroxy; or via substituted or unsubstituted Substituting (C3-C30)alkyl or (C3-C30) an alkenyl chain to an adjacent substituent to form one or more carbon atoms which may be replaced by at least one hetero atom selected from the group consisting of nitrogen, oxygen and sulfur a monocyclic or polycyclic alicyclic or aromatic ring; R21 to R27 have the same definition as one of R1 to Rio; a, b, e, and g are each independently represented by an integer from 1 to 4; When a, b, e or g is an integer of 2 or more, each Ri, each R2, each Rs or each R7 is the same or different; c, d and f are individually independent of 1 to 3 An integer; wherein, when c, d or f is an integer of 2 or more, each Rs, each R4 or each R6 is the same or different; and the heterocycloalkyl group and the (extended) heteroaryl group Containing at least one hetero atom selected from the group consisting of B, N, 0, S, P (=0), Si, and P. 2. The compound according to claim 1, wherein the substituted alkyl group in the Li and L2, Ri to Rio and .Ru to R27 groups, the substituted alkene a substituted alkynyl group, the substituted cycloalkylene group, the substituted cycloalkyl group, the substituted heterocycloalkyl group, the substituted (extended) aryl group, the substituted ( The heteroaryl group and the substituent on the substituted aromatic ring are each independently at least one selected from the group consisting of hydrazine, halogen, halogen substituted or unsubstituted (C1-C30). Alkyl, (C6-C30) aryl, 5- to 30-membered heteroaryl substituted by (C6-C30) aryl, (C3-C30)cycloalkyl, 5 95566 2 201249960 to 7 Heterocycloalkyl, (C1_C30)alkyldecyl, (C6_C3〇)aryldecyl, (C1-C30)alkyl(C6-C30)aryldecyl, (C2-C30)alkenyl, (C2 -C30)alkynyl, cyano, 咔α, ylamino, (C6-C30) arylamino, (C1-C30)alkyl (C6-C30) arylamine, (C6-C30 ) aryl boron carbonyl, (C1-C30) alkyl boron carbonyl, (C1-C30) institute (C6-C30) aryl benzyl, (C6-C30) aryl (C1-C30) alkyl, (C1-C30) alkyl (C6-C30) aryl, carbonyl, thiol, nitro and base. 3. The compound according to claim 1, wherein χι means CH or N; and Li and Lz are each independently selected from the group consisting of a single bond, a phenylene group, and a naphthyl group. , phenyl, extension, terphenylene, hydrazine, andeny lene, ke, phenanthrene, triphenyl, phenyl, phenylenylene, thiophene Base, propylene disulfide group, furanyl group, thienyl group, extension ratio B group, thiophenanthrene group, extension ratio thiol group, 嚷β siting group, stretching 嗔 哇 、, thiazole Basis, exozolylazole, exocarbazolyl, oxadiazole, exudate, arable, tetrazolium, tetrazolyl, tetrazolyl, exofuran, 0 to alpha, stretch beta卩 卩, π 密 咬 、, 卩 卩 卩 、, benzopyranyl, benzothiophene, benzofuranyl, benzoimidazolyl, benzothiazolyl, extens Benzoisothiazolyl, benzoisoxazolyl, benzoxazole, exoisoindyl, hydrazino, carbazolyl, benzodiazolyl, quinolinyl Isoquine Basis, 噌 噌 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基And sighed 95566 3 201249960 base. 4. The compound of claim 2, characterized in that The compound of claim 1, wherein the compound represented by the group is selected from the group consisting of: 95566 201249960 95566 5 201249960 95566 6 201249960 95566 7 201249960 6. An organic electric field illuminating device comprising the compound as described in claim 1 of the patent application. 95566 8 201249960 IV. Designated representative map: (1) The representative representative of the case is: (). (There is no picture in this case) (2) The symbol of the symbol of this representative figure is simple: (none) 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: 95566 2