TW201215658A - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

Abstract

The present invention relates to novel organic electroluminescent compounds and organic electroluminescent devices comprising the same. since the disclosed organic electroluminescent compounds have high luminous efficiency and excellent life property, OLED's having very good operation life can be manufactured therefrom.

Description

201215658 VI. Description of the Invention: [Technical Field] The present invention relates to a novel organic electroluminescent compound, and an organic electric field illuminating device comprising the same. Specifically, the organic electroluminescent (EL) compound of the present invention is represented by the chemical formula (1) or (2). Chemical formula (1)

Chemical formula (2)

[Prior Art] Among the display devices, an electric field light-emitting device as a self-luminous type display device is advantageous in that it has a wide viewing angle, excellent contrast, and a fast response rate. Eastman Kodak first developed an organic EL device using a low molecular weight aromatic diamine and aluminum complex as a material for forming an electric field [3 94882 201215658 luminescent layer [Appl phys 1987]. w, yid, in an organic EL device 'When an electric charge is applied to an organic layer formed between an electron injecting electrode (cathode) and a hole injecting electrode (anode), the electron disk is turned on to provide an exciton ((4) The light is emitted by using a self-illumination (scale or fluorescent). The organic EL device emits about 10 volts (V) of electricity; 8 μ, npn, and 100 to 10,000 turbid light (Cd) / / square metric m X-ray intensity of polarization. By simply selecting the way of fluorescent material, r, , y ' / leather long light. The device can be used in transparent flexible substrate nightmare: a and plasma display Compared with the panel or the inorganic 1^ display, the rn^1 rmi consumes low power but has a good color at a lower voltage (not more than 10V) operation.最The most important of its luminous efficiency and longevity, etc. (4) It should be applied to some of the requirements of the electric field storage materials, such as mobility, non-luminous quantum yield, high electron and hole holes. And form a uniform and stable material. The molecular structure 2 materials are generally classified into polymer materials and low molecular weight. The material contains IMP ^ female, low molecular materials including metal complexes and non-chelating human electric field luminescent materials. Such electroluminescent materials include raw dioxin (8, quinone-like) (10) compound, coumarin The blue to red of the derivative of the scented scent I, the derivative of the bismuth, and the visible light region can be obtained from the materials. 4 94882 201215658 In order to realize a full color OLED display, three kinds of electric field illumination are used. Materials (red, green, and blue), and the development of such electroluminescent materials with high efficiency and longevity are major issues that enhance the characteristics of overall organic electric field luminescence. Electric field luminescent materials can be classified into host materials and doping according to their functions. Agent materials. It is generally known that a device structure having the most excellent EL properties can be fabricated using an electric field light-emitting layer prepared by doping a dopant into a host material. Recently, in view of the EL required for a medium to large-sized OLED panel Performance, it is imperative to develop organic EL devices with high efficiency and longevity, and especially for the development of materials with better EL performance than conventional EL materials. The development of the host material is the most important pending issue of

One. The high purity and proper molecular weight of the host material (as a solid solvent and energy transmitter) enables vacuum vapor deposition. The glass-shift temperature and thermal decomposition temperature of the two sheets should be high enough to ensure heat = sex. Furthermore, the bulk material should have high electrochemical stability to provide long I. It is easy to form a defect film, and other adhesion to adjacent layers without interlayer migration. 〃. 呵 When the organic ion device is manufactured by the domain hybrid technology, the household molecules transfer the energy to the dopant in the excitatory state, and the host material also emits light. In the field light-emitting device, the color of the host material is destroyed by light, and the purity of the progenitor body _^ is improved. Not ~* said, but to the electric field luminescence lifetime and for the phosphorescent soil limbs, Lu, 4, 4, -Ν, γ - 94882 5 201215658 dicarbazole biphenyl (CBP) is by far the most widely known, and Efficient 0LEDs using hole barriers such as BCP and BAlq have been developed. Pioneer, Japan, etc. reported on the use of bis(2-mercapto-8-hydroxyquinolinyl)(p-phenylphenolyl)aluminum (111) (8 VIII) High performance 0LED.

These conventional materials are advantageous in terms of luminescence properties, but they have low glass transition temperatures and extremely poor thermal stability, so these materials tend to change during isothermal vacuum vapor deposition. In the 〇LED, the power efficiency = (Π / voltage current efficiency is defined. Therefore, the power efficiency is inversely proportional to the voltage. In order to obtain lower OLED power consumption, the power efficiency should be relatively low. In fact, using phosphorescent electric field luminescence ( EL) The current efficiency (cd/ampere (A)) exhibited by the LED is significantly higher than that of the OLED using the fluorescent EL material. However, conventional materials such as Mlq and CBP are used as the phosphorescent EL material. In the case of the host material, it is not as advantageous as the power efficiency (lumens/watt (lm/W)) because it has a higher operating voltage than the LED using the light-emitting material. 'In terms of Led's life, no matter what kind of hand & and can't be at a satisfactory level, it is necessary to develop a body material that can have better femininity and extreme improvement. 6 94882 201215658 The object of the present invention is to overcome the problems of the conventional techniques as described above, and to provide an organic electroluminescent compound having an excellent skeleton to obtain a luminous efficiency and an improvement as compared with a conventional material. Device Lifetime and Appropriate Color Coordinates Another object of the present invention is to provide an efficient and long-lived organic electric field illuminating device by using those organic electroluminescent compounds as an electric field luminescent material. [Technical Solution] The present invention relates to An organic electroluminescent compound represented by the chemical formula (1) or (2), and an organic electric field illuminating device comprising the same. By using the organic electroluminescent compound of the invention, (having a higher luminous efficiency and a significantly improved material lifetime property) ), can obtain 0LED with very good operating life. Chemical formula (1)

7 94882 201215658 Chemical formula (2)

A! to As and B! to Be independently represent N or CR2!; if two adjacent groups of Al to 尨 and Βι to Be represent CR21, these Rn groups may be via or without a fused ring. (C3-C30) an alkyl group or a (C3-C30) extending alkenyl group to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring; and the alkyl group of the alkyl group may pass through one or more a hetero atom substituted from NR31, hydrazine and S is substituted for 'the carbon atom of the alkenyl group may be substituted by N,

Li and the (C6-C30) extended aryl group with or without a substituent, or a (C3-C30) heteroaryl group with or without a substituent, the limitation is that it cannot be simultaneously represented with L2 Chemical bond

Ri to R3, R21 and Rsi independently represent hydrogen, gas, halogen, (C-C30)alkyl group with or without a substituent, (C6-C30) aryl group with or without a substituent, and one or more a substituted or unsubstituted (C6-C3 fluorene) aryl group having or without a substituent (C3-C30) cycloalkyl group, having a (C3-C30) heteroaryl group having or not having a substituent, having Or a 5- to 7-membered heterocycloalkyl group having a substituent of 5 to 7 members, or a substituted or unsubstituted 5- or 7-membered heterocycloalkyl group, with or without a substituent (10)-(10) cyclofilament, with or without (C3-C30) cycloalkyl substituted or unsubstituted (C3-C30) cycloalkyl, with or without a substituent, with or without Substituent (C7_C3〇)bicycloalkyl, cyano, NRiiRi2, BR13R14, PR15R16, p(=〇)Rl7Rl8 [wherein Rn group, (C2-C30) alkenyl group with or without a substituent, with or without

W represents -(CR5lR52)m_,, -0-, -Si(R54)(R55)-, _P(R56)-, -B(R58)_; to Ru independently represents with or without a substituent ( CLMO)alkyl, (C6-C30)aryl having or without a substituent (C3-C30)heteroaryl with or without a substituent], with or without a substituent ((n_C3〇) a fluorenyl group, a (C1_C30)alkyl (C6-C30) arylalkylene group with or without a substituent, a tris(C6_C3〇)aryldecylalkyl group with or without a substituent, with or without Substituent (C6_C3〇)aryl (cl_C3〇) alkyl group, (C1-C30) alkoxy group with or without a substituent, (C1-C30) sulfur-burning group with or without a substituent, with or (C6-C30) aryloxy group having no substituent, (C6_C3〇) aromatic sulfur with or without a substituent

Heart to Ru and heart to - as defined above to L and heart; and each of RS1 to R58 may be via (C3 C3〇)alkyl or (C3-C30) with or without a fused ring An alkenyl group is bonded to an adjacent substituent to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring; each of the heterocyclic and heteroaryl groups contains one or more selected from the group of 94882 9 201215658 B, N , 0, S, P (=0), heteroatoms of Si and P; and m represents an integer of 0, 1, or 2. Specifically, the group ^43 cco^ «42 with

It can be exemplified by the following structure:

Wherein R43 and R to R58 independently represent (C-C30)alkyl group with or without a substituent, (C6-C30) aryl group with or without a substituent, or with or without a substituent (C3- a C30)heteroaryl group, or each of R51 to R58, may be bonded to an adjacent substituent via a (C3-C30)alkylene group or a (C3-C30)alkylene group with or without a fused ring to form a lipid. Ring, or a single or multiple ring aromatic ring. [Embodiment] The "alkyl group" contained in the "alkyl group", "alkoxy group" and other substituents described herein includes both a straight chain group and a branched chain group. The term "aryl" as used herein means an organic radical derived from an aromatic hydrocarbon obtained by removing a hydrogen atom. The aryl group may be a monocyclic ring and a fused ring 10 94882 201215658, each ring suitably containing 4 to 7 ring atoms, preferably 5 or 6 ring atoms. Also included are structures in which two or more aryl groups are combined via a chemical bond. Specific examples include, but are not limited to, phenyl, naphthyl, biphenyl, anthryl, fluorenyl, fluorenyl, phenanthryl, orthotriphenyl (1:1'1 port 1^1171 € 1171), thiol, Sulfhydryl, fluorenyl, naphthacenyl, fluoranthenyl, and the like. The naphthyl group may be a 1-naphthyl group or a 2-naphthyl group, and the fluorenyl group may be a 1-fluorenyl group, a 2-fluorenyl group or a 9-fluorenyl group, and the fluorenyl group may be a 1-fluorenyl group or a 2-fluorenyl group. Any of 3-mercapto, 4-indenyl and 9-«yl. The term "heteroaryl" as used herein means one to four heteroatoms selected from the group consisting of B, N, 0, S, P (=0), Si and P as the aromatic ring skeleton atoms and as a residual aromatic. An aryl group of a carbon atom of a ring skeleton atom. The heteroaryl group may be a 5- or 6-membered monocyclic heteroaryl group or a polycyclic heteroaryl group fused to one or more benzene rings, and may be partially saturated. Also included are structures having one or more heteroaryl groups bonded via a single bond. The heteroaryl group may include a divalent aryl group in which the hetero atom is oxidized or quaternized to form an N-oxide, a quaternary salt or the like. Specific examples include, but are not limited to, monocyclic heteroaryl groups such as σ-fumanyl, 11-septyl, °-p, σm σ, 吼D, σ, β, thiadiazole Base, isothiazolyl, isoxazolyl, oxalylzolyl, fluorene fazolyl, triterpene, tetrahydronyl, tris(beta), tetras(yl), σ 丫, ° ratio , fluorenyl, thiol, fluorenyl; polycyclic heteroaryl, such as benzofluorenyl, benzothienyl, isobenzofuranyl, benzimidazolyl, benzothiazolyl, benzene Isothiazolyl, stupid isoxazolyl, benzoxazolyl, isodecyl, fluorenyl, 吲σ, benzo 11 dioxin, sulfonyl, isoinyl,噌琳基, 噎ϋ 琳 基 喧曙, 喧曙 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 基 11 11 11 11 11 11 11 11 11 11 11 11 11 11 11 11 11 11 11 11 11 11 11 11 11 11 11 11 11 11 11 11 11 11 11 11 11 Pyridyl N-oxide, sulfonyl N-oxide) and its quaternary salt. As described in the specification, "(C1-C30)alkyl, tri(C1-C30)alkyldecane, di(C1-C30)alkyl(C6-C30)aryldecyl, (C6-C30) The alkyl group in the aryl (Cl-C30) alkyl group, the (Cl-C30) alkoxy group, and the (Ci-C30)alkylthio group may have from 1 to 20 or from 1 to 1 such a limited number of carbon atoms. . "(C6-C30) aryl, bis(C1-C30)alkyl (C6-C30) aryl decyl, tris(C6-C30) aryl decyl, (C6-C30) aryl (C1-C30) The aryl group in the alkyl group, (C6-C30) aryloxy group and (C6-C30) arylthio group may have 6 to 20 or 6 to 12 limited carbon atoms. The hydroxy group in "(C3-C30)heteroaryl" may have 4 to 20 or 4 to 12 finite carbon atoms. The cycloalkyl group in "(C3-C60)cycloalkyl" may have 3 to 2 or 3 to 7 limited carbon atoms. The alkenyl or alkynyl group in "(C2-C30)alkenyl or alkynyl" may have 2 to 20 or 2 to 10 finite carbon atoms. The term "substituted or unsubstituted (with or without a substituent) j as used herein means that each substituent, L2, 仏 to R3, Rn to R18, r21 and R31 have one or more independently selected from Substituents of the following: 氘, _, (C, C30) alkyl with or without a halogen substituent, (C6-C30) aryl, with or without (C6-C30) aryl substituent (C3 -C30) a heteroaryl 5- to 7-membered heterocyclic alkyl group, a 5- to 7-membered heterocycloalkyl group fused to one or more aromatic rings, (C3-C30)cycloalkyl, and one or more Aromatic ring fused (C6-C30) cycloalkyl, tri(C1-C30)alkyldecyl, bis(C1-C30)alkyl (C6-C30) arylalkyl, tris(C6-C30) aryl Basestone, adamantyl, (C7-C30)bicycloalkyl, (C2-C30)alkenyl, (C2__C3()) 12 94882

201215658 缺基,基基,σ卡零坐基, NR6lR62, BR63R64, PR65R66, P(=0)Re7R68 [wherein 1^61 to R68 independently represent a (Cl-C30) alkyl group with or without a substituent, (C6-C30) aryl group with or without a substituent (C3-C30)heteroaryl group with or without a substituent, (C6-C30) aryl (C1-C30) alkyl group, (C1- C30) alkyl (C6-C30) aryl, (C1-C30) alkoxy, (C1-C30) alkylthio, (C6-C30) aryloxy, (C6-C30) arylthio, (C1 -C30) alkoxycarbonyl, (C1-C30)alkylcarbonyl, (C6-C30) arylcarbonyl, (C6-C30) aryloxycarbonyl, (C1-C30) alkoxycarbonyloxy, (C1 -C30) alkylcarbonyloxy, (C6-C30) arylcarbonyloxy, (C6-C30) aryloxycarbonyloxy, carboxy, nitro and hydroxy; or adjacent substituents bonded to each other Join to form a ring. The iAt group is selected from, but not limited to, the following structure

C"· 13 94882 201215658

In the above formula, r21 and r31 independently represent halogen, (H-C30)alkyl group having or without a substituent, (C6-C30) aryl group having or not having a substituent, and having one or more a substituted or unsubstituted (C6-C30) aryl group having no substituent (C3-C30) cycloalkyl group, a (C3-C30) heteroaryl group having or not having a substituent, and a center of NRnM (C1-C30)alkyl group with or without a substituent, (C6-C30) aryl group with or without a substituent or (C3-C30)heteroaryl group with or without a substituent independently of R12 a three (C-C30)alkyldecane group with or without a substituent, a (C1-C30)alkyl (C6-C30) arylalkylalkyl group with or without a substituent, with or without a substituent a tris(C6-C30)arylalkylene group, a (CU-C30) alkoxy group with or without a 201215658 substituent, a (C6-C30) aryloxy group with or without a substituent, with or without Substituted (C2-C30) alkenyl, with or without

And a (C2-C30) alkynyl group having a substituent, and W and R43 are as defined in the above chemical formulae (1) and (2). Group

Selected from, but not limited to, the following structure:

In the above formula, R! to R3 independently represent a (C1-C30)alkyl group having or not having a substituent or a (C6-C30) aryl group having or not having a substituent; R21 represents hydrogen, halogen, or (C1-C30)alkyl group having no substituent, (C6-C30) aryl group having or without a substituent, fused to one or more (C3-C30) cycloalkyl groups having or without a substituent Substituted or unsubstituted (C6-C30) aryl, (C3-C30)heteroaryl, with or without a substituent, NRnR12 [wherein Rn to R18 independently represent with or without [s] 15 94882 201215658 Alkyl (C1-C30)alkyl, (C6-C30)aryl with or without a substituent or (C3-C30)heteroaryl with or without a substituent], with or without a substitution a tris(C1-C30)alkyldecylalkyl group, a bis(C1-C30)alkyl (C6-C30)aryldecylalkyl group with or without a substituent, three with or without a substituent (C6-C30) An aryl rock base with or without a substituent

W and R43 are as defined in the above chemical formulas (1) and (2). The organic electroluminescent compound according to the present invention can be specifically exemplified by the following compounds, but is not limited thereto.

16 94882 201215658

17 94882 201215658

18 94882 Θ 201215658

The method for preparing the organic electroluminescent compound according to the present invention is specifically exemplified by the reaction scheme (1), but is not limited thereto. Reaction scheme (1)

In this reaction scheme, R3 is as defined in the above chemical formulas (1) and (2), and X represents dentate. .: Month also provides an organic electric field illuminating device comprising a first electrode '*two electrode' and a [94882 19 201215658 or a plurality of chemical formulas (]) interposed between the first electrode and the second electrode An organic layer, wherein the organic layer comprises an organic electroluminescent compound represented by one or (2). The organic layer includes an electric field luminescent layer, and the material field luminescent layer contains an organic electric field luminescent compound ' as shown in the chemical formula (1) or (2) as a host material, and one or more kinds of dopants. The dopant to be applied to the organic electroluminescence device of the present invention is not particularly limited, but is preferably selected from the compounds represented by the chemical formula: Chemical Formula (3) Μ 丨 L101L 丨 02L103 wherein M1 is a metal selected from the group consisting of : Group 7, 8th, 9th, 10th, 11th, 13th, 14th, 15th and 16th, and the ligand, L1. 2 and l1 (>3 is independently selected from the following structures: 20 94882 S) 201215658

Wherein R 2 < n to R 2 〇 3 independently represent hydrogen (C1-C30)alkyl group with or without a halogen substituent, (C6-C30) aryl with or without (C1-C30) alkyl substituent Or a halogen; R204 to R219 independently represent hydrogen, (C1-C30)alkyl group with or without a substituent, ((n-C30) alkoxy group with or without a substituent, with or without a substituent (C3-C30) cycloalkyl, (C2-C30) alkenyl group with or without a substituent, (C6-C30) aryl group with or without a substituent, mono- or not having a substituent - Or a di-(C1-C30)alkylamino group, [21 94882 201215658 mono- or di-(C6_C3〇)arylamino group with or without a substituent, sFs' with or without a substituent (c克C3〇) burnt stellite, bis(C1-C30)alkyl (C6_C3〇) aryl decyl group with or without a substituent, tris(C6_C3Q) arylhetero group with or without a substituent, cyanide a group, or a dentate; to R223 independently represents hydrogen, (ci C30) alkyl group with or without a _ s substituent, or (C6-C30) aryl group with or without (C1_C30) alkyl substituent; Ruler 224 R225 independently represents hydrogen, (Cl C30)alkyl group with or without a substituent, (C6_c3 fluorene) aryl group with or without a substituent, or halogen ' or with via a fused ring (c3ci2) a stretching group or (C3-G12)-alkenyl phase linkage to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring;

Rm represents a (C1-C30) alkyl group having or not having a substituent, a (C6-C30) aryl group having or not having a substituent, a (C5-C30) heteroaryl group having or not having a substituent, or Prime

Rm to R229 independently represent hydrogen, (c-C30)alkyl group with or without a substituent, (C6_C3〇)aryl group with or without a substituent, or halogen; Q represents *V232 XV , R236 R236 ^ ^ 5^240, wherein R231 to Rm independently represent hydrogen, (C-C30) alkyl group with or without a halogen substituent, (C1-C30) alkoxy group, _ 素, with or without a substituent (C6 -C30) aryl, cyano, or (C5-C30) 22 94882 201215658 cycloalkyl with or without a substituent; or each of R231 to R242 may be bonded to an adjacent group via an alkyl or an alkenyl group Substituents to form a spiro or fused ring, or each of R23I to R242 may be bonded to R2G7 or R208 via a stretch or an alkenyl group to form a saturated or unsaturated fused ring. The dopant compound represented by the chemical formula (3) can be obtained by the following compounds

23 94882 201215658

The organic electroluminescence device of the present invention may further comprise an arylamine compound and a styyl arylamine compound, in addition to the organic electroluminescent compound represented by the chemical formula (1) or (2). One or more compounds of the group formed. Examples of such arylamine compounds or styrylarylamine compounds are disclosed in Korean Patent Application No. 10-2008-0123276, No. 10-2008-0107606, and No. 10-2008-0118428, but are not limited thereto. this. In the organic electric field light-emitting device of the present invention, the organic layer may further include one or more metals selected from the group consisting of: in addition to the organic electroluminescent compound represented by the chemical formula (1) or (2): a transition metal, a lanthanide metal, and a d-transition element of the organometallic group of Group 1 of the periodic table, Group 2, the fourth and fifth cycles, or a complex thereof. The organic layer may include both an electric field luminescent layer and a charge generating layer. The organic electric field illuminating device may include, in addition to the organic electric field luminescent compound represented by the chemical formula (1) or (2), a blue or green light 24 94882 201215658 or a red or one layer of an organic electric field luminescent layer to form An organic electric field illuminating device that emits white light. A compound which emits blue light, green light or red light is disclosed in Korean Patent No. 10-2008-0123276, No. 10-2008-0107606, and No. 10-2008-0118428, but is not limited thereto. In the organic electric field illuminating device of the present invention, it is preferable to provide one or more layers (hereinafter referred to as "surface layer") selected from a chalcogenide layer, a metal halide layer and a metal oxide layer. An inner surface of at least one side of the pair of electrodes. Specifically, it is preferable to dispose a chalcogenide compound layer of the ceramsite with an aluminum metal (including an oxide) on the anode surface of the electric field luminescent medium layer, and to provide a metal dentate layer or a metal oxide layer to the electric field illuminating The cathode surface of the dielectric layer. Thereby, operational stability can be obtained. Examples of the chalcogen compound preferably include Si〇x (l$X$2), A10); Si ON, S i A1 ON, and the like. Examples of the metal compound include LiF, MgF2, Cab, a fluoride of a rare earth metal, and the like. Examples of the metal oxide preferably include CszO, Li2, MgO, SrO, BaO, CaO, and the like. In the organic electric field light-emitting device of the present invention, it is preferable that 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 provided in the electrode pair manufactured as described above. At least one surface. Thereby, the electron transporting compound is reduced to an anion, thereby facilitating the injection and transport of electrons from the mixed region to the EL medium. Further, since the hole transporting compound is oxidized to form a cation, the hole is promoted from the mixed region to be injected and transported to the EL medium. Preferred oxidizing dopants include various Lewis acids and acceptor compounds (accept〇r C0mp0un(j). Preferred reducing dopants include alkali metals, alkali metal compounds, alkaline earth metals, and rare [25 94882 201215658] Earth metal and mixtures thereof. A white electric field illuminating device having two or more layers of an electroluminescent layer can be produced by using a reducing dopant layer as a charge generating layer. Since the organic electroluminescent compound of the present invention has high luminescence Efficiency and excellent material life characteristics, and thus an OLED having a very high operational life can be produced from the organic electroluminescent compound. Best Modes The present invention is further illustrated by reference to a representative compound of the present invention to further illustrate the organic electroluminescent compound of the present invention. The method of preparing the compound, and the luminescent properties of the device made from the compound, but the examples are intended to be illustrative only, and are not intended to limit the scope of the invention in any way. [Preparation 1] 10) Preparation

Preparation of Compound (1-1) A solution of 1,3 -dibromobenzene (20 g (g), 84.77 mmol (mmol)) dissolved in THF (500 mL (mL)) was cooled to -78 °C. n-Butyllithium 26 94882 201215658 (n-BuLi, 2. 5M, 33.9 mL, 84.77 mmol) was slowly added to the solution, and the mixture was stirred at -78 C for 1 hour. Triphenylsulfonium chloride ((C6H5)3sici) (29. 9 g) dissolved in thf (100 mL) was added thereto. The mixture was slowly warmed to ambient temperature and stirred for 12 hours. After extracting the mixture with ethyl acetate, the extract was washed with distilled water and an aqueous solution of NaCl, and dried with water-free MgS 4 and dried under reduced pressure. Recrystallization from dioxin and decyl alcohol (mc: MeOIM: 10) gave Compound G-1) (18 g, 95%). Preparation of Compound (1-2) A solution of Compound (i-i) (2 g, 96.06 mmol) dissolved in THF (600 mL) was cooled to -78. n-BuLi (2.5 M, 43.2 mL, 108.08 mmol) was slowly added to the solution, and the mixture was stirred at -78 ° C for 1 hour. Tridecyl borate (16.06 mL, 144.11 〇1) was added thereto. The mixture was slowly warmed to ambient temperature and stirred for 12 hours. After extracting the mixture with ethyl acetate, the extract was washed with distilled water and aqueous NaCl solution, dried over anhydrous Mg?? Recrystallization from dioxane and calcination (1:10) gave compound (1-21) (12 g, 35%). Preparation of Compound (1-3) Sodium hydride (NaH, 60% in mineral oil) (3.3 g, 83.90 〇1) was diluted with DMF (10 mL). A solution of oxazole (11.2 g, 67.12 mmol) dissolved in DMF (60 mL) was then added. The mixture was stirred at ambient temperature for one hour. A solution of 2,4-di-pyrimidine (i〇g, 67.12 mmol) dissolved in DMF (60 mL) was added and the mixture was stirred at ambient temperature for 4 hr. Distilled water (40 mL) was then added and the mixture was extracted with dichloromethane. The extract was washed with hydrazine and aqueous NaCl solution and dried with anhydrous MgS 4 . 94882 27 201215658 Distillation under reduced pressure. The compound (1_3) (4.0 g, 21%) was obtained by column chromatography. The compound (10) is prepared in a reaction tube, and the compound g_3) (3.8 g, 13·58 cut ιοί), the compound (1-2) (6.2 g, 16. 3 〇 〇 1) are stirred under reflux at 120 ° C. A mixture of Pd(PPh3)4 (784 mg (mg), 0.67 mmol), 2M Na2C〇3 solution (7 mL), ethanol (50 mL) and toluene (200 mL) for 12 hours. After cooling to ambient temperature, the mixture was extracted with ethyl acetate and the extract was washed with distilled water and aqueous NaCI. Recrystallization from ethyl acetate gave Compound (1 〇) (5. 5 g, 69%). [Preparation Example 2] Preparation of Compound (16)

The compound (2-1) was prepared in a reaction tube, and 2-gas-3-nitropyridine (25 g, 157.6 mmol), benzene succinic acid (24.9 g, 204.9 mol), Pd (PPh3) 4 were stirred under reflux. (5. 4g, 4. 73mmol), a mixture of K2C〇3 (54.48g, 394.2mmol), steaming water (15〇mL), toluene (300mL) and ethanol (100mL) for 12 hours. The mixture was then cooled to room temperature and steamed to the water. The resulting mixture was extracted with a gas purge, and the extract was dried with MgS 4 and distilled under reduced pressure. Purification by column chromatography gave compound (2-l) (30 g, 149.

28 94882 201215658 95. 45%) Preparation of hydrazine compound (2-2) Compound (2-l) (30 g, 149.85 mmol) was mixed with triethyl phosphine (150 mL), and the mixture was stirred at 180 ° C. hour. After cooling to ambient temperature, the reaction mixture was distilled under reduced pressure. The compound (2-2) (2. lg, 12.48 mmol, 8.37%) was obtained by column chromatography. Preparation of Compound (2-3) According to the same synthetic procedure for the preparation of Compound (1-3) in Preparation 1, Compound (2-3) (2.6 g, 7.99 mmol, 60. 1 ° /.) was obtained. Preparation of Compound (16) Compound (16) (3. lg, 5.33 mmol, 67%) was obtained according to the same procedure for the preparation of compound (10). [Preparation Example 3] Preparation of Compound (19)

The compound (3-1) was prepared in a reaction tube, and bromine-2-nitroacridine (30 g, 145.8 mmol), 1-naphthalene acid (30.6 g, 178.2 mmol), Pd (PPh3) was stirred under reflux. a mixture of 4 (5.148, 4.45111111〇1), 2^11 (2〇〇3 aqueous solution (297.01111111〇1), toluene (500 mL) and ethanol (200 mL) for 4 hours. The mixture was then cooled to ambient temperature and distilled water was added. The resulting mixed [S] 29 94882 201215658 was extracted with ethyl acetate, and the extract was dried with anhydrous MgS 4 and distilled under reduced pressure. Compound (3-1) was obtained by column chromatography. 31 g, 123. 3mmo 1, 84. 03%). The compound (3-2) was prepared in a reaction tube, and the compound (3-l) (31 g, 124.3 mmol) and triethylphosphine (300 mL) were The mixture was stirred under reflux for 10 hours. After the mixture was cooled to ambient temperature, the organic solvent was evaporated under reduced pressure. distilled water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous Mg?? The compound (3-2) (18 g, 82.84 mmol, 66.81%) was obtained by column chromatography. The compound (3-3) was prepared according to the solvent. The same synthetic procedure as used in the preparation of the compound (Bu 3) in Preparation Example 1 gave Compound (3-3) (19 g, 51.04 mmol, 61.6%). Preparation of Compound (19) According to Preparation 1 10) The same synthetic procedure gave Compound (19) (16.3 g, 25.9 mmol, 50.1%). [Preparation Example 4] Preparation of Compound (61) 30 94882

201215658

Preparation of Compound (4-1) NBS (8.33 g, 46.80 mmol) was added to a solution of Compound (19) (19@, 42.54111111〇1) dissolved in DMF (200 mL). After stirring for 10 hours at ambient temperature, the organic solvent was evaporated under reduced pressure. Distilled water was added to the residue, and the resulting mixture was extracted with ethyl acetate. The extract was dried over anhydrous MgS 4 and evaporated under reduced pressure. The compound (4-1) (20 g, 38.06 mmol, 89.47%) was obtained by column chromatography. Preparation of Compound (4-2) According to the same synthetic procedure for the preparation of Compound (1-2) in Preparation 1, Compound (4-2) (8 g, 16.31 mmol, 42.86%) was obtained. Preparation of Compound (4-3) According to the same synthetic procedure for the preparation of Compound (3-1) in Preparation 3, Compound (4-3) (7 g, 12.33 mmol, 75.62%) was obtained. Preparation of Compound (4-4) 31 94882 201215658 The compound (4-4) (4 g, 7.46 mmol, 58.33%) was obtained according to the same synthetic procedure for the preparation of Compound (3-2). Preparation of Compound (61) Compound (4-4) (4 g, 7.46 mmol), iodobenzene (1.25 mL, 11.20 mmol), copper (0.71 g, 11.20 mmol), 18- A mixture of crown-6 (0.15 g, 0.59 mmol), K2C 3 (3.1 g, 11.20 mmol) and 1,2 dichlorobenzene (100 mL) was allowed to stand for 15 hours. After the mixture was cooled to ambient temperature, the mixture was evaporated and evaporated. The extract was washed with distilled water, dried over anhydrous MgSO.sub. The residue was purified by column chromatography to afford compound (j) (3. 6 g, 5. 88 mmol, 78.88%). [Preparation Example 5] Preparation of Compound (62)

Preparation of Compound (5-1) According to the same synthesis procedure used in Preparation Example 3 for the preparation of Compound (3-1), but using dibenzo[b,d]furan-4-ylboronic acid, a compound (5- 1) (llg, 38. 02mmol, 89.22%). Preparation of Compound (5-2) According to the same synthetic procedure for the preparation of Compound (3-2) in Preparation 3, 32 94882 201215658, Compound (5-2) (8 g, 31.09 mmol, 81.78%) was obtained. Preparation of Compound (5-3) According to the same synthetic procedure for the preparation of Compound (1-3) in Preparation 1, Compound (5-3) (7.4 g, 20.11 mmol, 65.66%) was obtained. Preparation of Compound (62) Compound (62) (5.8 g, 8.65 mmol, 43.28%) was obtained according to the same synthetic procedure for the preparation of compound (10). Organic electroluminescent compounds (compounds 1 to 70) were prepared according to the same procedures as described in Preparations 1 to 5. The ruthenium R and MS/FAB data of the prepared organic electroluminescent compound are shown in Table 1. Table 1 Compound NMR (CDCI 3. 200 MHz) MS/FAB Measured value 1 δ = 0.25 (9 Η, s), 7.25-7.36 (4 Η, m), 7.49-7.5 (3 Η, m), 7.63-7.7 (4 Η , m), 7.79(2Η, m), 7,94(1Η, m), 8.12(1Η, m), 8.55(1Ht m) 391.58 391.18 2 δ = 7.25~7.37(20Hf m)( 7.6W.68( 5H,m), 7·76~7·79(3Η, m), 7.94(1Η·m), 8.12(1H, m),8·55(1Η, m) 577.79 577.22 7 δ = 2.34(3H, m ), 7.25-7.37(1 OH. m), 7.46*7.68(14H, m), 7.79(2H, m). 7.89_7.94(2H, m), 8·12(1Η· m), 8.55(1H , m) 591.81 591.24 10 δ = 7.25-7.37(20H, m), 7.61~7.63(2H, m), 7.76(1 H, m), 7·96.96(3H, m). 8·12(1Η , m). 8·55~8·57 (2Η, 579.76 579.21 13 δ = 7.25~7.37(22H, m), 7.61-7.66(4H, m), 7.76(1 H, m), 7.94-7.95(2H , m), 8.08~8.12(2H, m), B.55(2H, m) 627.85 627.24 16 δ * 7.22-7.25(2H, m), 7.33~7.46(14H, m), 7.55(3H, m) , 7.61 (1Ht m), 7.76(1H, m), 7.89-7.97(4H, m), 8.43(1H, m), 8.57(1H, m), 8.74(1 H, m) 580.75 580.21 19 δ = 7.25 (1H, m), 7.33~7.46(14H, m), 7.55(3H, m), 7.61-7.67(5H, m), 7.76(1 H, m), 7.89-7.96(3H, m), 8.16( 1 H, m), 8.54~8.57 (3 H, m) 629.82 629.23 33 94882 201215658 25 δ = 7.16(1 Η. m), 7.36-7.46(15Η, m), 7.55-7.61 (5Η, m), 7.76(1 Η, m), 8.06(1 H , m), 8.38~8.43(3H, m), 8.51 (1H, m), 8.57(1 H. m). 8.83(1 H, m) 631.80 631.22 27 δ = 7.37-7.55(29H, m), 7.61 ~7.62(2H, m), 7.69(1 H, m), 7.76-7·77(3Η, m). 7.87(1 H, m), 8{1H,m), 8.09(1 H. m), 8.18(1 H, m) 729.98 729.29 31 δ = 7.06(1 H, m), 7.37-7.55(19H, m), 7.61-7.67(6H, m), 7.76(1 H, m), 7.92(1 H m), 8.09(1 H, m). 8.16(1 H, m), 8.22(1 H, m), 8.54(1 H, m) 645.84 645.23 33 δ = 1.72(6H, s), 7.17(1 H, m), 7.25(1 H, m), 7.29(1 H, m), 7.33(1 H, m), 7.34(1 H, m), 7.37(6H, m), 7.42-7.55(16H, m), 7.76(1 H, m), 7.87~7.94(3H.m), 8.12(1 H, m), 8.55(1 H, m) 693.95 693.29 34 δ = 7.25~7.33(3H, m), 7.42 (1H, m), 7.5(1H, m), 7.59-7.68(14H, m), 7.76-7.79(3H, m), 7.94-8(10H, m), 8.1~8.12(4H, m), 8.55 (1H, m) 727.96 727.27 37 δ = 7_25-7.34(9H, m), 7.42-7·5(8Η· m)· 7.6 Bu 7.68(5H, m)· 7.76-7.79(3H( m), 7.94( 1H, m), 8.12(1H, m), 8.55(1H, m) 631.76 ^ 631.19 39 δ = 7.25-7.37(10H, m), 7.46-7.55(11Hf m)t 7.61-7.68(4H(m)( 7.79{2H, m)t 7.89-7.94(2Hf m), 8.12(1H, m), 8.55( 1Ht m) 577.79 577.22 44 δ = 7.25-7.37(1 OH, m), 7.46-7.55(11H, m), 7.61-7.63(2H, m). 7.88-7.96(4H, m), 8.12(1 H, m), 8.55~8.58(2H, m) 578.78 578.22 45 δ = 7.25-7.37(1 OH, m), 7.46-7.55(11H, m), 7.61-7,63(2H, m), 7.89-7.94( 2H, m), 8.12(1 H, m), 8.55(1 H, m), 9.42(2H, m) 579.76 579.21 54 δ = 7.25-7.37(24H, m), 7.61-7.63(3H, m), 7.76(1 H, m), 7.94(1 H, m), 8.12(1H, m), 8.55(1H, m), 9.42(2H, m) 655.86 655.24 55 δ = 725(2H, m), 7.33( 2H, m), 7.37(6H, m). 7.42-7,5(17H, m), 7.76(1H, m), 7.94(2H, m), 8.12(1H, m), 8.38(1H. m) , 8.55(2H, m), 8.59(1 H,s) 745.94 745.27 58 δ = 7.25(1 H, m), 7.33(1 H, m), 7.37(6H, m), 7.42-7.52(15H, m ), 7.76(1 H, m), 7.94-7.98(2H, m), 8.05(1 H, m), 8.45(1 H, m), 8.55(1 H, m), 9.42{2H, m) 685.91 685.20 60 δ = 7.25(2H, m), 7.33(2H, m), 7.37(6H, m), 7.42(1 H, m), 7.45(1 H, m), 7.46-7.58(19H. m), 7.76{1H, m), 7.94(2H, m), 8.55(2H, m), 9.42(2H, m) 795.01 79 4.29 61 5 = 7.29(1 H, m), 7.37(6H, m), 7.4(1 H, s), 7.42-7.5(11H, m), 7.55(4H, s). 7.55-7.67(6H. m ), 7.76(1 H, m), 7.89-7.96(4H, m), 795*01 794.29 34 94882 201215658 8.12~8·16(2Η, m), 8·54~8·57(2Η,m) 62 δ = 7.13(1Η, m), 7.25(1Η, m), 7.32-7.46(16Η, m), 7.55(3Η, m), 7.61-7.66(2Η, m), 7.76(1 Η, m), 7.89 ~7.96(5Η, m), 8.55-8.57(2Η, m) 669*84 669.22 65 δ = 7.22{1Η, m), 7.29(1Η, m), 7.37(6Η, m), 7.4(1Η, s) , 7.42-7.5(11 Η, m), 7.55(4Η, s), 7.55-7.63(5Η, m), 7.76(1 Η, m), 7.97(1 Η, m), 8.12(1 Η, m) , 8.43(1 Η, m), 9.42(2Η, m) 745.94 745.27 66 δ = 7.22~7.25(2Η, m), 7.33(1 Η, m), 7.37(6Η, m), 7.42-7.5(17Η, m), 7.76(1 Η, m), 7.94~7.97(2Η, m), 8.38-8.43(3Η. m), 8.55(1 Η, m), 8.59(1 Η, s) 746.93 746.26 68 δ = 7.25 ~7.33(3Η, m), 7.42(1Η, m), 7.5(1Η, m), 7.61-7.63(2Η, m), 7.76(1Η, m), 7.89~7.96(3Η, m), 8.12(1Η , m), 8.55-8.57 (2Η, m) 594.86 594.31 70 δ = 7.14(1Η, m), 7.25-7.33(3Η, m), 7,5-7.51(5H, m), 7.63-7.66 (5Η, m), 7.76-7.79 (4Η, m), 7.94·7. 96(2Η, m), δ.12(1Η, m), 8.51-8.57(5Η, m) 582.73 582.20 [Example 1] Use of the present invention by the use of an OLED device using an organic electroluminescent compound according to the present invention The electric field luminescent compound produces an OLED device. First, a transparent electrode ΙΤ0 film (15 Ω / Π) made of OLED (Samsung Corning) glass was washed with a mixture of trichloroethylene, acetone, ethanol, and steamed water in the order of ultrasonic waves, and stored in isopropyl alcohol for use. Then, the ΙΤ0 substrate was assembled in the substrate holder of the vacuum deposition apparatus. 4, 4', 4"- gin (Ν, Ν-(2-naphthyl)-phenylamino)triphenylamine (2-oxime) (the chemical formula is shown below) is placed in the chamber of the vacuum deposition apparatus Thereafter, the chamber is vented to a vacuum of 10-6 torr. A current was applied to the chamber to evaporate 2-TNATA, thereby providing a vapor deposition of a hole injection layer having a thickness of 60 nm on the IT0 substrate. Next, Ν,Ν'-bis(α-naphthyl)-indole, Ν'-diphenyl-4,4'-diamine (ΝΡΒ) is added to another chamber of the vacuum deposition apparatus, and the chamber is力力ρς; 35 94882 201215658 Current to evaporate npb' to thereby provide a vapor deposit of a 20 nm thick hole-transmitting layer on the hole injection layer.

After the hole injection layer and the hole transport layer are formed, the electric field light-emitting layer is deposited thereon in the following manner. The compound (12) of the present invention was filled into a chamber of one of the true air phase deposition apparatuses as a host material, and Ir(ppy) 3 (the structure of which is shown below) was filled in another chamber as a dopant. The two materials were volatilized at different rates, and the gas phase was provided at a concentration of 4% by weight to 10% by weight. Therefore, an electric field luminescent layer having a thickness of 30 nm was vapor-deposited on the hole transport layer.

Then, on the electroluminescent layer, vapor-deposited bis(2-mercapto-8-hydroxyindolyl)(p-phenylphenolyl)aluminum(III) (BAlq) was used as a hole barrier with a thickness of 5 nm. A layer, vapor-deposited ginseng (8-hydroxyquinoline) aluminum (III) (Alq) was used as an electron transport layer having a thickness of 20 nm, and then an 8-electron group was vapor-deposited as an electron injecting layer having a thickness of 1 to 2 nm. Then, another vacuum vapor deposition apparatus was used to vapor-deposit a 36 94882 201215658 I-lu cathode having a thickness of 150 nm, thereby producing an OLED.

Each of the materials used to fabricate the OLED was purified as a field illuminant after 10_6 Torr by vacuum sublimation. [Example 2] Manufacture of an OLED device using an organic electric field luminescent compound according to the present invention An OLED device was produced in the same manner as described in Example 1 except that the hole blocking layer was not contained. [Example 3] An OLED device was produced by the same process as described in Example 1 by using the OLED device using the organic electroluminescent compound according to the present invention, but the compound of the present invention as a host material was used in the electroluminescent layer ( 12) And, compound (19) and (piq) 2lr (acac) replace the dopant Ir(ppy)3.

[Example 4] Manufacture of an OLED device using an organic electric field luminescent compound according to the present invention An OLED device was fabricated by the same process as described in Example 3 except that the hole barrier layer was not provided. [Comparative Example 1] An OLED device was fabricated by the same process as described in Example 1 by using a conventional LED of the electroluminescent material, but changed to a cell of the vacuum vapor deposition device using CBP instead of the compound of the present invention. The main material in the body.

[Comparative Example 2] An OLED device was fabricated by the same process as described in Example 3 by the manufacture of a 0 LED using a conventional electroluminescent material, but changed to a cell of the vacuum vapor deposition device using CBP instead of the compound of the present invention. The main material in the body. The luminous efficiency of the OLED including the organic electroluminescent compound of the present invention (Examples 1 to 4) and the luminous efficiency of the OLED including the conventional EL compound (Comparative Examples 1 and 2) were measured at 1,000 cd/(m 2 ), respectively. The results are shown in Table 2. 38 94882 201215658 Table 2 No. Main body dopant hole barrier operating voltage (V) @1000 cd/m2 Luminous efficiency (cd/A) EL color @1000cd/m2 Example 1 1 Compound 5 Ir(ppy)3 BALq 6.7 24 Green 2 Compound 6 Ir(ppy)3 BALq 6.8 26 Green 3 Compound 10 Ir(ppy)3 BALq 6.6 30 Green 4 Compound 12 Ir(ppy)3 BALq 6.7 32 Green 5 Compound 28 Ir(ppy)3 BALq 6.8 32 Green 6 Compound 44 Ir(ppy)3 BALq 6.7 24 Green 7 Compound 46 Ir(ppy> BALq 6.9 25 Green Example 2 8 Compound 5 Ir(ppy)3 - 6.5 26 Green 9 Compound 10 Ir(ppy)3 - 6.6 27 Green 10 Compound 12 Ir(ppy)3 - 6.5 34 Green Example 3 11 Compound 19 (piq) 2lr(acac) BALq 6.5 7.1 Red 12 Compound 32 (piqMr(acac) BALq 6.3 7.3 Red 13 Compound 56 (piqMr(acac) BALq 6.5 7.4 Red 14 Compound 57 (piqMr(acac) BALq 6.4 7.6 Red 15 Compound 61 (piq>Ir(acac) BALq 6.2 7.4 Red 16 Compound 67 (piqMr(acac) BALq 6.2 7.5 Red Example 4 17 Compound 57 (piq) 2lr(acac) - 6.0 7.7 Red 18 Compound 61 (piqMr(acac) - 6.1 7.5 Red 19 Compound 64 (piqMr(acac) - 6.0 7.3 Red 20 Compound 66 (piq)dr(acac) - 6.1 7.2 Red Comparative Example 1 CBP lr(ppy)3 BALq 7.5 18.5 Green Comparative Example 2 CBP (piq)2lr(acac) BALq 7.3 6.8 Red As shown in Table 2, the electroluminescent compound developed by the present invention has excellent characteristics in terms of its performance compared with the conventional material. Further, the organic electroluminescent compound of the present invention as a host material is used. The device not only has excellent luminescent properties but also lowers the operating voltage, confirming the improved luminous efficiency. [Simple description of the diagram] Benefit [Key component symbol description] Benefit 39 94882

Claims (1)

201215658 VII. Patent application scope: 1. Organic electroluminescent compound represented by chemical formula (1) or (2): Chemical formula (1) Chemical formula (2) Wherein, to & and 匕 to Bs independently represent n or CRu; if 相邻ι to A and two adjacent ones of B1 to β8 represent CR2, then the R21 may be g-with or not/, slightly a heterocyclic (G3_(10)) stretching group or (6)_c3〇) an alkenyl phase linkage to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring; and the alkyl group of the alkyl group may be passed through one or more a hetero atom substituted from Us S and wherein the carbon atom of the exo group may be substituted by N, L4L2 independently chemically bonded, (C ^ C3G) extended aryl with or without a substituent or with or without a substituent (C3-C30) Heteromeric Group's condition is that Li#L2 does not correct the time to indicate a chemical bond; 94882 40 201215658 匕 to R3, R21 and (5) independently represent hydrogen, deuterium, halogen, with or without a substituent ( C (C30) leucoyl, (C6-C30) aryl group with or without a substituent, substituted or unfused with one or more (C3-C30) cycloalkyl groups with or without a substituent a substituted (C6-C30) aryl group, a (C3-C30)heteroaryl group with or without a substituent, a 5- to 7-membered heterocycloalkyl group with or without a substituent, and one or a substituted or unsubstituted 5 to 7 membered heterocycloalkyl group having a plurality of aromatic rings, a (C3-C30) ring-based group having or without a substituent, fused to one or more aromatic rings Substituted or unsubstituted (C3-C30)cycloalkyl, Orthogonal, with or without a substituent, (C7-C30)bicycloalkyl, cyano, NR11R12, BR13R&quot ;, Pr15r16, P(=0)RnRls [the center to Rie independently represents (C1-C30)alkyl group with or without a substituent, (C6-C30) aryl group with or without a substituent or has or (C3-C30)heteroaryl group having no substituent, tri(C1-C30)alkyldecanealkyl group with or without a substituent, di(C1-C30)alkyl group with or without a substituent (C6) -C30) aryl decyl group, a (C6-C30) aryl decyl group with or without a substituent, (C6-C30) aryl (C1-C30) alkyl group with or without a substituent, with or (C1-C30) alkoxy group having no substituent, (C1-C30) alkylthio group with or without a substituent, (C6-C30) aryloxy group with or without a substituent, with or without Substituents of (C6-C30) aryl group, with or without a substituent group of (C2-C30) alkenyl group, with or without a substituent group of 4,194,882,201,215,658 w represents -(CR5IR52)„-, -(R51)C=C(R52)—, _N(R53)-, -S-,-0-, -Si(R54)(R55)—, _p(R56)_ , _p(=〇)(R57)_, -C(=0)- or -B(R58)-; to R43 and RS1 to R58 are as defined above for Ri to & and R2i; and each of Rsi to R58 An alicyclic ring or a monocyclic or polycyclic aromatic ring may be bonded to an adjacent substituent via a (C3-C30)alkylene group or a (C3_C3〇)alkylene group with or without a fused ring; Each of the heterocycloalkyl and heteroaryl groups contains one or more heteroatoms selected from the group consisting of B, Μ, 〇, S, P (=〇), si, and p; and m represents an integer 〇, ι or 2. The organic electroluminescent compound according to claim 2, wherein each of the substituents L1, L2, R1 to 匕, Ru to Ri8, R21 and r31 is further selected from the group consisting of the following: Substituted by one or more substituents: an aryl group, a (U-C30) alkyl group with or without a halogen substituent, a (C6-C30) aryl group, with or without a (C6_C3〇) aryl substituent (C3-C30)heteroaryl, 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl, slightly bonded to one or more aromatic rings, (C3 -C30)cycloalkyl, (C6-C30)cycloalkyl, tri(C1-C30)alkylalkyl, bis(n-C3〇)alkyl(C6_C3〇)aryl fused to one or more aromatic rings Anthracenyl, tris(C6~C30)arylalkylalkyl, adamantyl, (C[C3〇)bicyclohexyl, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano, carbazole 42 94882 201215658, NR6lR62, BR63R64, PR65R66, P(:0)R67R68 [wherein Rei to R68 independently represent a (Cl-C30)alkyl group with or without a substituent, with or without a substituent (C6- C30) aryl or (C3-C30)heteroaryl] with or without a substituent, (C6-C30) aryl (C1-C30) alkyl, (C1-C30)alkyl (C6-C30) aryl , (C1-C30) alkoxy, (C, C30) alkylthio, (C6-C30) aryloxy, (C6-C30) arylthio, (C1-C30) alkoxycarbonyl, (C1 -C30)alkylcarbonyl, (C6-C30)arylcarbonyl, (C6-C30)aryloxycarbonyl, (C1-C30)alkoxycarbonyloxy, (C1-C30)alkylcarbonyloxy, ( C6-C30) arylcarbonyloxy, (C6-C30) aryloxycarbonyloxy, sulfhydryl, nitro and thiol; or adjacent substituents bonded to each other To form a ring. 3. The organic electroluminescent patent range luminescent compound, Paragraph 1, wherein 43 94882 201215658 cfe cfo 03⁄4 c&b Wherein R21 and R31 independently represent halogen, (n-C30)alkyl group with or without a substituent, (C6-C30) aryl group with or without a substituent, and one or more with or without a substitution a substituted or unsubstituted (C6-C30) aryl group having a (C3-C30) cycloalkyl group, a (C3-C30)heteroaryl group with or without a substituent, NRnRi2 [wherein Rn and Ri2 (C-C3)alkyl group having or without a substituent, (C6-C30) aryl group having or having no substituent of 44 94882 201215658 or (C3-C30) having or without a substituent Aryl], a tri(C1-C30)alkyldecane group with or without a substituent, a bis(C1-C30)alkyl(C6-C30)aryldecylalkyl group with or without a substituent, with or without a (C6-C30) arylalkylalkyl group having a substituent, a (C1-C30) alkoxy group having or not having a substituent, a (C6-C30) aryloxy group having or not having a substituent, with or without (C2-C30) alkenyl group having a substituent, with or without a substituent W and R43 are as defined in the first item of the patent application. For example, the organic electroluminescent compound of claim 1 of the patent scope, wherein Is selected from the following structure Wherein, Ri to R3 independently represent a (C6-C30) aryl group with or without a substituent ((n-C30〇s 45 94882 201215658 alkyl or with or without a substituent; R21 represents hydrogen, halogen, having Or a (n-C30) alkyl group having no substituent, a (C6-C30) aryl group having or not having a substituent, and one or more (C3-C30) cycloalkyl groups having or without a substituent a substituted or unsubstituted (C6-C30) aryl group, (C3-C30)heteroaryl group with or without a substituent, NRnR12 [wherein Rn to R18 independently represent with or without a substituent ( C1-C30)alkyl, (C6-C30) aryl with or without a substituent (C3-C30)heteroaryl with or without a substituent], with or without a substituent (C1- C30) a decyl calcinyl group, a bis(C1-C30)alkyl group (C6-C30) aryl decyl group with or without a substituent, a tri(C6-C30) aryl decyl group with or without a substituent (C6-C30) aryloxy group with or without a substituent, W and R43 are as defined in the first item of the patent application. 5. An organic electroluminescent compound according to claim 1 of the patent application, which is selected from the group consisting of: 46 94882 201215658 47 94882 201215658 48 94882 201215658 6. An organic electric field illuminating device comprising an organic electroluminescent compound according to any one of items 1 to 5 of the patent application. For example, the organic electric field of the sixth aspect of the patent application system includes a first electrode, a second electrode, and a layer or a plurality of organic layers interposed between the first electrode and the second electrode; A layer package comprising one or more organic electroluminescent compounds such as those in the scope of claims 5 to 5 and one or more of the formula (3), 94882 49 201215658 agent: chemical formula (3) M1l, oilI02l103 wherein Μ1 is a metal selected from the group consisting of: 7th, 8th, 9th, 1st, 1st, 13th, 14th, and Group 15 and Group 16; and the ligand L1.1, L1.2 and L103 are independently selected from the following structures: 50 94882 丨S) 201215658 Wherein R201 to R2D3 independently represent hydrogen, (a-C30)alkyl group with or without a halogen substituent, (C6-C30) aryl group with or without (C1-C30) alkyl substituent, or ii R2〇4 to R219 independently represent hydrogen, (C1-C30)alkyl group with or without a substituent, (C-C30) alkoxy group with or without a substituent, with or without a substituent (C3-C30) cycloalkyl, (C2-C30) alkenyl group with or without a substituent, (C6-C30) aryl group with or without a substituent, mono- or di- or -(a-C30)alkylamino group, mono- or di-(C6-C30)arylamino group with or without a substituent, SF5, tri-r 51 with or without a substituent 94 94882 201215658 (C1- C30) a sulphur base group, a bis(C1-C30)alkyl group (C6-C30) aryl group with or without a substituent, a bis(C6-C30)^r group with or without a substituent Broken yard, cyano, or a nutrient; R22. To Rm independently represent hydrogen, (n-C30)alkyl with or without a halogen substituent, or (C6-C30) aryl with or without (n-C3〇)alkyl substituent; R224 independently of Rm Represents hydrogen, (C1-C30)alkyl with or without a substituent, (C6-C30) aryl with or without a substituent, or halogen; or Rm and Rm via or without a fused ring ( C3-C12) alkylene or (C3-C12)-alkenyl phase linkage to form an alicyclic ring, or a monocyclic or polycyclic aromatic ring; Rm represents a (q-C30) alkyl group with or without a substituent, (C6-C30) aryl group with or without a substituent, (C5-C30) heteroaryl group with or without a substituent, or halogen; Rm to R229 independently represent hydrogen, with or without a substituent ( C1-C30)alkyl, (C6-C30) aryl with or without a substituent, or halogen; ^231 .^232 R2MR234. R237 R238^24lR242 R235R236 ^ ^ R2M R240?, wherein Rui to Rm independently represent hydrogen, (Cl-C30) alkyl group with or without a halogen substituent, (C1-C30) alkoxy group, halogen, having Or (C6-C30) aryl, cyano, or (C5-C30) cycloalkyl having or without a substituent; or RM, to Rm2 each via extension 94882 52 201215658 A thiol or an extended alkenyl group is bonded to an adjacent substituent to form a spiro or fused ring, or each of R231 to R242 may be bonded to R2 <n or R208 via an alkyl or alkenyl group to form a saturated group. Or an unsaturated fused ring. 8. The organic electroluminescent device of claim 7, wherein the organic layer comprises one or more amine compounds selected from the group consisting of an arylamine compound and a styrylarylamine compound, and is selected from the group consisting of One or more metals of the following group: organometallics of Group 1 of the Periodic Table of the Elements, Group 2, transition metals of the 4th and 5th cycles, lanthanide metals, and d-transition metals. 9. The organic electroluminescent device of claim 7, wherein the organic layer comprises an electric field luminescent layer and a charge generating layer. 10. The organic electric field illuminating device of claim 7, which is a white luminescent organic electric field illuminating device comprising one or more layers of an additional organic electric field luminescent layer that emits blue, red or green light. 53 94882 201215658 IV. Designation of representative drawings: (1) The representative representative of the case is: () Figure (2) The symbol of the symbol of the representative figure is simple: 5. If there is a chemical formula in this case, please reveal the characteristics that can best show the invention. Chemical formula: Chemical formula (1) Chemical formula (2) 2 94882