TW201111473A - Novel organic electroluminescent compounds and organic electroluminescent device using the same - Google Patents

Abstract

Provided are a novel organic electroluminescent compound and an organic electroluminescent device using the same. Since the organic electroluminescent compound disclosed herein exhibits good luminous efficiency and excellent life property compared to the existing host material, it may be used to manufacture OLED devices having very superior operation life and consuming less power due to improved power efficiency.

Description

201111473 VI. Description of the Invention: [Technical Field] The present invention relates to a novel organic electroluminescent compound, and an organic electric field light-emitting device using the same. More specifically, the organic electric field luminescent compound is represented by the chemical formula (1): Chemical formula (1)

[Prior Art] In an display device, an electric field illumination (electr〇iuminescent, el) device is advantageous in that it has a wide viewing angle, excellent contrast, and fast response speed as a self-luminous display device. Eastman K〇dak first opened in 1987 | an organic EL device using a low molecular weight aromatic diamine and a complex of Rhodamine as a substance for forming an electroluminescent layer [_• Foot & ensemble 51, 913, 1987' 〇

In an organic EL device, when an electric charge is applied to an organic layer formed between an electron injecting electrode (drag) and an electric/injecting electrode (anode), electrons and holes are turned on and formed to generate excitons. Light is emitted in a state in which the excitons are deactivated by using electric field luminescence (phosphorescence or fluorescence). The organic EL device emits polarized light at a voltage of about 10 volts (v) and a high luminance of 100 to 10, and a candle light (cd) / square meter (m2). The organic EL device has the property of emitting light from the blue to red spectral range by simply selecting a glory material. The organic EL 3 94940 201111473 device is advantageous in that it can be formed on a transparent flexible substrate (such as plastic) compared to a plasma display panel or an inorganic EL display, which can be used at a lower voltage (10 V or lower). ) Operation, low power consumption, and excellent surface quality in organic EL devices, the most important factor in determining its luminous efficiency and operational efficiency is the electric field luminescent material. Some of the requirements for the electric field luminescence = solid state high field luminescence quantum yield, high electron/hole mobility, decomposition resistance during vacuum deposition, ability to form = and stability. 14 membrane organic electric field luminescent materials can be roughly divided into high molecular weight materials and low eight substances and metal-free pure organic substructures are divided into metal mismatch packages: ginseng (8, cycline conjugate, coumarin derivative =: Alkene: Bio- and bis(phenethyl-based aryl)-derived two materials. It is reported that the frequency and other materials: the electric field of the green field emits light. #目Μ到,π色光光区

In order to achieve full-color organic hair I (red, green Μ) ^: 峨 ) ) 赫 赫 , , , , , , , , , , , , , , , , , , , , , , , , , , , In order to enhance the red, green and blue color of the organic electricity life, the focus is on the development of high efficiency and long-term aspects which can be divided into main materials and luminescent materials. The EL material is doped into the body from its functional dopants. It is generally believed that the structure of the device can be achieved by performance. Recently, the development of the most beneficial device for injuring the rainbow layer has become an urgent need to solve the problem of organic el' with high efficiency and long life. In particular, considering the medium-sized to 94940 4 201111473 large-scale OLED panel, the development of materials that are far superior in efficiency, especially the most important subject to be solved by R&D is the main material to be solved. Energy transfer agent), the main material (as a solution to make vacuum vapor deposition possible: this; purity and suitable molecular thermal decomposition temperature should be high enough, to achieve the high temperature of the glass transition temperature and material In terms of stability, the high adhesion of the host material to adjacent materials is 'Z °, and it is easy to form a film. When an organic thin EL is formed in an amorphous thin layer with no interlayer mobility, it is excited. The energy transfer of the state material and the dopant 2 can not reach 100%, and the main body is emitted from the host material: in the case of emitting red light device, by the nature, the main wavelength of the nine wavelengths has a higher blending ratio. The larger the visible agent, the dark light of the two materials causes the color purity to degrade. If the technology is applied, the 4 (4) force luminescence lifetime and the enthalpy is improved. The material 1 is the most widely recognized subject material for phosphorescent materials. Report Containing BCP, m1Q etc. of the hole-blocking layer efficiency, Japan first Crimson Corporation (Pioneer) describes the use of BAlq derivative and the like is high at first glance it can Xin body 0LED. 5 94940 201111473

BAlq Derivatives Although these materials provide good electric field luminescence characteristics, their thermal stability is very poor due to their low glass transition temperature and may degrade during high temperature deposition in vacuum. Since the power efficiency of the OLED is given by the (Π/voltage) x current efficiency, the power efficiency is inversely proportional to the voltage. High power efficiency is required to reduce power consumption. In fact, OLEDs using phosphorescent materials provide much higher current efficiencies (candles per ampere (cd/A)) than those using phosphors. However, when an existing material such as BAlq, BCP or the like is used as a host of a phosphorescent material, there is no significant power efficiency (lumens (lm) / watt (w)) than that of the OLED using a fluorescent material because of its high driving voltage. Moreover, the OLED device does not have a satisfactory operational life. Therefore, it is still necessary to develop a more stable and efficient host material. SUMMARY OF THE INVENTION Accordingly, it is an object of the present invention to provide an organic electroluminescent compound which has improved luminous efficiency and device operating life compared to existing materials, and has an excellent skeleton to solve the aforementioned problems, and the skeleton has a suitable 6 94940 201111473 color coordinates. Another object of the present invention is to provide another embodiment of the present invention and an organic electroluminescent device which provides a further effect and long life using the organic electric field to illuminate into β. Set. High Technical Solution for 电场 Electric Field Luminescent Material The present invention provides the following chemical formula. A novel organic light-emitting compound represented by the formula (1), and an organic electric field light-emitting device using the compound electromechanical core σ. Since the organic electric field-emitting compound according to the present invention exhibits good luminous efficiency and superior lifetime properties, it can be used to manufacture a lion-shake having a very excellent operational life and consuming lower power (due to improved power efficiency). Chemical formula (1)

among them,

Ad VIII 3 is independent of (3) or Ν, but excludes ^ to & also ck;

An and An are independently represented by hydrogen, (C6-C3G)aryl having or without a substituent, or (G3_(10))heteroaryl, with or without a substituent, and R and Ri to R12 independently represent hydrogen and deuterium. , halogen, (C1-C3G) with or without a substituent, (C6-C3〇) aryl with or without a substituent, and one or more (C3_G3〇) with or without a substituent Environmentally-based fused or substituted (C6_C3〇) aryl, (C3-C3())heteroaryl with or without a substituent, 5 members with or without substituents 7 94940 201111473 a 5-membered heterocycloalkyl group, a 5- to 7-membered heterocycloalkyl group fused to one or more aromatic rings having or not having a substituent, a (C3-C30) cycloalkyl group having or not having a substituent, (C3-C30)cycloalkyl, cyano, schochyl, NR21R22, BR23R24, PR25R26, P(=0)R27R28 slightly adjacent to one or more aromatic rings with or without a substituent [its center to R28 independent (C1-C30)alkyl group with or without a substituent, (C6-C30) aryl group with or without a substituent or (C3-C30) with or without a substituent Aryl], R29R3〇R3lSi-[wherein R29 to R31 independently represent (C1-C30)alkyl group with or without a substituent, (C6-C30) aryl group with or without a substituent or with or without a substituted (C3-C30)heteroaryl group, a (C6-C30)aryl (C1-C30)alkyl group with or without a substituent, wherein X represents S or 0, and R32 represents (N-C30)alkyl group having no substituent, (C6-C30) aryl group with or without a substituent or (C3-C30)heteroaryl group with or without a substituent], with or without a substitution a (C2-C30)alkenyl group, a (C2-C30) alkynyl group having or without a substituent,

Or R and h to R12 may be bonded to an adjacent substituent via a (C3-C30)alkylene group or a (C3-C30)alkylene group with or without a fused ring to form an alicyclic ring, a single ring or more An aromatic ring of a ring or a heterocyclic ring of a monocyclic or polycyclic ring; W system means - (CR5lR52)m-, -(R51)C = C(R52) -, -N(R53) -, -S-, -0 ---Si(R54)(R55)---P(R56)---P(=0)(R57)----COO)- or _B(R58)-; 94940 201111473 feet 41 to R43 and R51 to R58 are the same as R1 to Rl2; the heterocycloalkyl or heteroaryl group may contain one or more hetero atoms selected from the group consisting of B, N, fluorene, S, P (=0), Si, and P; Represents an integer 〇, 1 or 2. Specifically, the structure is exemplified independently.

By the following

And 1 to to 8 are independently represented by (C1-C30)alkyl group having or without a substituent, (C6_c3〇)aryl group having or not having a substituent, or (10)__heteroaryl having or without a substituent. a group, or R43 and R51 to di-gamma Γγ», via an ((3)(10)) extended or an alkenyl group with or without a fused ring, bonded to an adjacent substituent to form an alicyclic, monocyclic ring aromatic ring and A monocyclic or polycyclic heteroaryl ring. [Embodiment] In the present invention, the "alkyl" alkoxy group and other substituents containing a "burning 94940 9 201111473 base" moiety include both a straight chain and a branched chain. In the present invention, "aryl" By means of an organic radical obtained by removing a hydrogen atom from an aromatic hydrocarbon, may comprise from 4 to 7 members, especially a single or fused ring of 5 or 6 members, including a plurality of aryl groups linked by a single bond. Specific examples include phenyl, naphthyl, biphenyl, anthracenyl, fluorenyl, decyl, phenanthryl, triphenylenyl, fluorenyl, fluorenyl, chrysenyl, fused tetraphenyl (naphthacenyl), fluoranthenyl, etc., but is not limited thereto. The naphthyl group includes a naphthyl group and a 2-naphthyl group, and the fluorenyl group includes a 1-fluorenyl group, a 2-fluorenyl group, and a 9- The fluorenyl group, and the fluorenyl group includes a 1-position, a 2-position, a 3-mercapto group, a 4-fluorenyl group, and a 9-fluorenyl group. In the present invention, the "heteroaryl group" means a mixture as an aromatic ring. One to four hetero atoms of the skeleton atom selected from B, N, 0, S, P (=〇), Si, and P, and an aryl group as a carbon atom of the remaining aromatic ring skeleton atom. The heteroaryl group may be a 5- or 6-membered monocyclic heteroaryl group or a polycyclic heteroaryl group obtained by condensation with a benzene ring, and may be partially saturated. Further, the heteroaryl group includes a linkage by a single bond. More than one heteroaryl group. The heteroaryl group includes a divalent aryl group, wherein the hetero atom in the ring may be oxidized or quaternized to form, for example, an N-oxide or a quaternary salt. Specific examples include a monocyclic heteroaryl group. Base, ~ age base, _ group, base, sulfhydryl, radio, sylvestre, sulphate, (four) silk, 卩f money, two money, called base, base, trisal, tetrasal "咕基" is more than a dentate group, a cyclyl group, a phenylene group, a polycyclic heteroaryl group, such as a benzofluorenyl group, a benzophenone, a broad and a stupid (4) group, a stupid base, a stupid and an anthracene, a stupid嗔 嗔 嗔 苯 曙 曙 曙 ♦ base, benzo. sit-based, iso-based, ah, 94940 10 201111473 benzopyrene, 啥 基 、, 啥 啥 基, 琳 基 啥嗤, 琳 基 啥嗤, 啥嗤 啥嗤Base, thiol, base, benzo, benzo(tetra) (benzQdi_iyi) ¥ 'N_oxide (eg pyridyl N_oxide, quinolinyl n-oxide, etc.), its four Salt, etc., but not limited to this. In the present invention, '(C1~C30) succinyl, tris(cl_C3〇) calcene, 4a-C30) alkyl (C6-C30) aryl sylylene, (C6_C3 fluorene) aryl ((H- C30) a base group, a (CK30) alkoxy group, a (C1-C3〇) sulphur group, and the like may have from 1 to 20 carbon atoms, more preferably (1) to 1 carbon atom. (C6-C30) aryl, bis(c-C3〇)-based (10) aryl sulphide, S(C6-C30) aryl sylvestre, (C6_C3 fluorene) aryl (6)-(10)) alkyl, The aryl group of the C6-C30) aryloxy group, (C6-C30) arylthio group or the like may have 6 to 20 carbon atoms, more specifically 6 to 12 carbon atoms. The aryl group of "(C3-C30)heteroaryl" may have 4 to 2 carbon atoms, more specifically 4 to 12 carbon atoms. "(C3_C3〇)cycloalkyl, cycloalkyl group may have from 3 to 20 carbon atoms, more specifically from 3 to 7 carbon atoms. (C2-C30) alkenyl or alkynyl" alkenyl or alkyne The base may have from 2 to 2 carbon atoms 'more specifically 2 to 1 carbon atoms. And, in the present invention, the phrase "substituted or unsubstituted, or ''with or without a substituent" means An, An, R, 1 to r12, R21 to R32, heart to R43 and heart to The substituent of R58 may be independently substituted with one or more substituents selected from the group consisting of hydrazine, halogen, (C-C30) alkyl group with or without a halogen substituent, (C6-C30) aryl group. (C3-C30)heteroaryl group with or without (C6-C30) aryl substituent, 5- to 7-membered heterocycloalkyl group, 5- to 7-membered fused with one or more aromatic rings Cycloalkyl, 94940 201111473 (C3-C30)cycloalkyl, (C6_C3〇)cycloalkyl fused to one or more aromatic rings, RaRbReSi- [Ra, Rb, Re independently represent (C1-C30) alkane Or (C6-C30) aryl], (C2-C30) alkenyl, (C2-C30) alkynyl, cyano, sulphate, NRdRe, BRW, PRf, P(=〇)r鲈[Rd to Rk is independently represented by (π, C3〇) alkyl, (C6-C30) aryl or (C3-C30)heteroaryl], (C6-C30) aryl (C1-C30) alkyl, (C1-C30) Alkyl (C6-C30) aryl, fx- [X ^ represents S or 0, R1 represents (C1-C30) alkyl, (C6-C30) aryl (C3-C30)heteroaryl], rx(=〇)_[r<» represents (c-C3〇)alkyl, (C1-C30)alkoxy, (C6-C30)aryl or (C6 -C30) aryloxy],

RmC(=0)0-[r represents (C1_C30)alkyl, (cl_C3〇)alkoxy, (C6-C30)aryl or (C6-C30)aryloxy], carboxyl, nitro and hydroxy, Alternatively, it may be bonded to an adjacent substituent to form a ring. When h to Rs are bonded to an adjacent substituent via an alkyl or alkenyl group

Is selected from the following structures, but is not limited to this

Formed _ Ri", r4, r5, r7, R8, Rg, Ri., Ru and Ri2 are independently hydrogen (hydrogen, halogen, halogen, with or without a substituent ((n_c30) alkyl, with or without The aryl group of the substituent or the (C3-C30) heteroaryl group having or without a substituent 94940 12 201111473.

It is selected from the following structures, but is not limited to this:

Wherein R, An and An each independently represent hydrogen (C6 C3G) aryl group with or without a substituent or (6)-(10)) heteroaryl group with or without a substituent.匕 to ^ independently means hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, iso-T, tert-butyl, pentyl, pentyl, hexyl, heptyl, octyl, fluorene Base, fluorenyl, fluorine, gas, bromine, phenyl, naphthyl, 2-naphthyl, N-hydrazinyl, phenyl phenyl, decyl, N-phenyl _2, N-phenyl- 3-oxazolyl, N-phenyl-4-yl-carbazolyl, 2-pyridyl, 3-pyridine, 4-pyridyl, quinolinyl, 6-quinoxalinyl, phenanthrenyl, 2-phenanthrene , 3—phenanthryl, 4-phenanthryl or 9-phenanthryl; R, An and An are independently represented by hydrogen, phenyl, naphthyl, 2-naphthyl, biphenyl, 2-quinolinyl, 3-quinoxa Orolinyl, 4-quinolinyl, 5-quinolinyl, 6-quinolinyl, 7-quinolinyl, 8-quinolinyl, 9H-indol-2-one, 9H-indol-3-one, egg --4-ketone, ketone, N-carbazolyl, N-phenyl-indole-carbazolyl, N-phenyl-2-oxazolyl, N-phenyl-3-oxazolyl, N- Phenyl-4-oxazolyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 1,2, 3-trit-4 -ketone, 1,2, 3-trin-5-one, 1, dimorph-2-one, N-7H-benzo[c]carbazolyl, N_phenyl-7H_ And carbazole 9,494,013,201,111,473. Sit _10_嗣, N_phenyl_7H_benzo[c]nkajun_11_®, N_phenyl_7H_benzo[c]flavor β sitting_9_嗣, N-phenyl- 7H-benzo[〇]° card° sit-8-S, 1-σ indolyzynyl, 2-mercapto, 3-吲t·well, 5-° fluorenyl, 6-吲耕基,7-吲耕基, 8-吲耕基,6-dibenzofuranyl, 7-dibenzofuranyl, 8-dibenzofuranyl, 9-dibenzofuranyl, diphenyl Dibenzoborol-6-one, dibenzocyclopentylboran-7-one, dibenzocycloborane-8-one, dibenzocyclopentane-9 -ketone,

, 3-isoindolinyl, 1-isoindolinyl, 4-isoindolinyl, 5-isoindolinyl, 6-isoindolinyl, 7-isoindolinyl, 8-isoindole or Ν-π is pyridine and [2, 3-b] fluorenyl, and R, An and Ar22 are phenyl, naphthyl, biphenyl, quinalyl, fluorenyl, phenanthryl, ° ratio 11, and The sulfhydryl group, the fluorenyl group, the lysine group, the sulfonium group, the ND carbyl group or the N-7H-benzo[c] odor 11 group may be further substituted with one or more substituents selected from the group consisting of: Mercapto, phenyl, triphenyldecyl, trimethyldecyl, N-carbazolyl, cyano, fluoro, decyloxy, trifluoromethyl and cyclohexyl. More specifically, the organic electroluminescent compound according to the present invention is independently selected from the following structures, but is not limited thereto. 14 94940 201111473

15 94940 201111473

16 94940 201111473

17 94940 201111473

18 94940 201111473

N

19 94940 201111473

The organic electroluminescent compound according to the present invention can be prepared by the following reaction scheme (1): Reaction scheme (1)

In the reaction scheme (1), A! to A3, An, An, and R! to R12 are the same as defined in the chemical formula (1) and the chemical formula 20 94940 201111473 (2). Provided is an organic electric field light-emitting device according to the present invention, comprising: a first electrode; a second electrode; and one or more organic layers interposed between the first electrode and the second electrode; wherein the organic layer One or more organic electroluminescent compounds represented by the chemical formula (1) are contained. The organic layer comprises an organic electroluminescent layer comprising one or more dopants and one or more organic electroluminescent compounds of the formula (1) as a host. 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 following chemical formula (3). Formula (3) M1L101L102L103 wherein M1 is selected from the group consisting of the following groups: Group 7, Group 8, Group 9, Group 10, Group 11, Group 13, Group 14, Group 15. And the Group 16 metal, and the ligands Lm, L1Q2 and L103 are independently selected from the following structures: 21 94940 201111473

^2t5 ^214

^2»

R20S R2J9

R222

Wherein R201 to R2()3 are independently represented by hydrogen, (a-C30)alkyl group having or without a halogen substituent, (C6-C30) aryl group having or not having an (n-C30)alkyl substituent; Or halogen; R204 to R219 are independently hydrogen, with or without a substituent 22 94940 201111473 (C1-C30)alkyl, (cl_C3〇)alkoxy with or without a substituent, with or without a substitution (C3_C3〇)cycloalkyl, (C2-C30)alkenyl with or without a substituent, (C6_C30)aryl with or without a substituent, mono or di (cl_C3) with or without a substituent 〇)alkylamino group, mono- or di(C6_C3〇)arylamine group with or without a substituent, SFs, tri(C1_C30)alkyldecanealkyl group with or without a substituent, with or without a substituent a bis(C1-C30)alkyl (C6-C30) arylalkylene group, a tris(C6-C30)aryldecylalkyl group with or without a substituent, a cyano group or a halogen; R22. The Rm series independently represent (C1-C30)alkyl or (C6-C30) aryl with or without a halogen substituent; R224 and Rm are independently represented Hydrogen, (C-C30)alkyl with or without a substituent, (C6 C3 fluorene) aryl with or without a substituent, or i- or Km and R225 may be 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 (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 a halogen;

Km to R229 independently represent hydrogen, (C1-C30)alkyl group with or without a substituent, (C6_C3〇)aryl group with or without a substituent, or halogen; and 94940 23 201111473 Q series

Wherein R231 to R242 independently represent hydrogen (C1-C30) alkyl group with or without a halogen substituent, (C1-C30) alkoxy group, dentate, with or without a substituent (C6-C30) An aryl group, a cyano group, or a (C5-C30) cycloalkyl group with or without a substituent, or 1^231 to R242 may be bonded to an adjacent substituent via an alkylene group or an alkenyl group to form a spiro ring. Or a fused ring, or 1^231 to R242, may be bonded to R207 or Rm via an alkyl or alkenyl group to form a saturated or unsaturated fused ring. The dopant compound of the formula (3) can be specifically exemplified by a compound of the following structure, but is not limited thereto. 24 94940 201111473

25 94940 201111473

In the organic electronic device of the present invention, the organic layer may further include a group selected from the group consisting of an arylamine compound and a styrylarylamine compound, in addition to the organic electroluminescent compound represented by the chemical formula (1). One or more compounds. The arylamine compound or the styrylarylamine compound is exemplified in Korean Patent Application No. 10-2008-0123276, No. 10-2008-0107606, and No. 10-2008-0118428, but is not limited thereto. . Furthermore, in the organic electric field light-emitting device of the present invention, the organic layer may further comprise one or more metals selected from the group consisting of: in addition to the organic electroluminescent compound represented by the chemical formula (1): Transition metal, lanthanide metal and d-transition element of organometallic, Group 2, 4th and 5th cycles. The organic layer may include an electric field luminescent layer and a charge generating layer. 26 94940 201111473 4 Furthermore, the organic layer may include one or more layers of an organic electric field light-emitting layer that emits blue light, red light or green light in addition to the organic electroluminescent compound to realize an electric field light-emitting device that emits white light. The compound which emits blue light, red light or green light is exemplified in Korean Patent Application No. 10-2008-0123276, No. 10-2008-0107606, and No. 10-2008-0118428, but is not limited thereto. In the organic electric field light-emitting device of the present invention, a layer (hereinafter referred to as "surface layer") selected from a chalcogenide layer, a metal halide layer and a metal oxide layer is provided on the electrode pair. On the inner surface of one or both of the electrodes. More specifically, a layer of chalcogenide (including oxide) of bismuth or aluminum may be disposed on the anode surface of the electroluminescent luminescent medium layer and a metal-based layer or a metal oxide layer may be disposed on the luminescent medium layer. On the surface of the cathode. Thereby, operational stability can be obtained. The chalcogenide compound may be 'such as Si〇x (lSxS2), Al〇x (lSx$1.5), SiON, SiAlON or the like. The metal halide may be, for example, a fluoride of LiF, MgF2, CaF2, a rare earth metal, or the like. The metal oxide may be 'such as Cs2〇, LhO, MgO, SrO, BaO, CaO, or the like. In the electric field light-emitting device according to the present invention, it is also preferred to provide a mixed region of the electron transporting compound and the reducing dopant or a mixed region of the hole transporting compound and the oxidizing dopant in the electrode pair to be manufactured. On at least one surface. In this case, since the electron transporting compound is reduced to an anion, it becomes easier to inject and transport electrons from the mixed region to the electric field illuminating medium. In addition, since the hole transporting compound is oxidized to form a cation, it becomes easier to inject and transport the hole from the mixed region to the electric field illuminating medium. 27 94940 201111473 Preferred oxidizing dopants include various Lewis acids and acceptor compounds. Preferred reducing dopants include metallurgical, metal-measuring compounds, soil-measuring metals, rare earth metals, and mixtures thereof. Further, an organic electroluminescence device for emitting white light having two or more layers of an electroluminescent layer can be prepared by using a reducing dopant layer as a charge generating layer. Advantageous Effects Since the organic electroluminescent compound according to the present invention exhibits good luminous efficiency and excellent lifetime properties as compared with existing host materials, it can be used to manufacture an OLED device having a very good operational life and consuming lower power (due to improved power efficiency). . Mode for Invention The present invention will be further described in detail with respect to the organic electroluminescent compound according to the present invention, the preparation process of the compound, and the electric field luminescent properties of the apparatus using the compound. However, the following specific examples are provided for illustrative purposes only and are not intended to limit the scope of the invention. [Preparation Example] [Preparation Example 1] Preparation of Compound (1)

Preparation of compound (1-1) 9H-tribenzo[b,d,f]azepine (10 g (g), 41.10 mmoles 28 94940 201111473 (mmol)), 2,4-dichloro ° ratio bite (7. 29 g, 49. 32 mmol), Pd (0Ac) 2 (0. 46 g), NaOt-bu (7.9 g, 82. 20 mmol), toluene (100 ml (mL) And P(t-bu)3 (2 mL, 4.11 mmol, 50% in benzene) was mixed and stirred under reflux. After 10 hours, the mixture was cooled to room temperature and distilled water was added. After extracting with EA and drying over anhydrous MgSO4, dried under reduced pressure, and then obtained by the column column to obtain compound (1-1) (8 g, 22.54 mmol, 54.99%). Preparation of Compound (1): Compound (1-1) (8 g, 22.54 mmol), phenyl benzoic acid (4.12 g, 33.81 mmol), Pd(PPh3)4 (2.6 g, 2. 25 mmol), Cs2C〇3 (14.69 g, 45. 09 mmol), distilled water (15 mL), toluene (100 mL) and ethanol (40 mL) were mixed and stirred under reflux. After 12 hours, the mixture was cooled to room temperature and distilled water was added. After extracting with EA and drying with anhydrous MgS 4 , the mixture was evaporated under reduced pressure, and then compound (1) (3 g, 7. 56 mmol, 33.66%) was obtained by column separation. [Preparation Example 2] Preparation of Compound (47)

Preparation of Compound (2-1) 2, 4,6-Trichloromethane (10 g, 54.51 mmol), phenylphosphonic acid (16.6 g, 136.29 mmol), Pd (PPh3) 4(3. 15 g, 2.72 mmol), 2M K2C〇3 (50 mL), toluene (100 mL) and ethanol (30 mL) were mixed and spoiled under reflux at 29 94940 201111473. After 4 hours, the mixture was cooled to room temperature and water was added to the mixture. After extracting with EA and drying with anhydrous MgS 4 , the mixture was distilled under reduced pressure, and then Compound (2-1) (7 g, 26.24 mmol, 48.14%) was obtained by column separation. Preparation of Compound (47) NaH (1.57 g, 39·1 ,1, 60% in methanol oil) was added to DMF (70 mL) and Compound (2-1) (7 g, 26.24 mmol) was dissolved. In DMF (60 mL). After 1 hour, 9H-tribenzo[b,d,f]azepine (7.98 g, 32.8 mmol) was dissolved in DMF (70 chaos). After mixing for 1 hour, add steamed water. The compound (47) (7 g, 14.78 mmol, 56.33%) was obtained by extraction with EA and dried over anhydrous MgSO. [Preparation Example 3] Preparation of Compound (96)

Preparation of Compound (3-1) THF (100 inL) was added to NaH (4.2 g, 105.74 mmol, 60% in mineral oil) and 9H-tribenzo[b,d,f]nitrogen The solution (13.6 g, 81.34 mmol) was dissolved in THF (100 mL). At -20. The reaction solution was added to 2,4,6-three-gas three-pill (16.5 g, 89.47 mmol) and THF (100 mL). After mixing for 4 hours, distilled water was added. After extracting with EA and drying with anhydrous MgS 4 , distillation under reduced pressure, followed by column separation to obtain 30 94940 201111473 compound (3-1) (7 g, 22. 21 mmol, 27. 30%) ). Preparation of Compound (3-2) Compound (3-1) (7 g, 22.21 mmol) was dissolved in THF (200 mL), and lyophilized phenyl (8.1 mL, 24.43 mmol, 3. 0M was slowly added to the mixture in the mixture. After 5 hours, steamed crane water was added, extracted with EA and dried over anhydrous MgS 4 , and then distilled under reduced pressure, followed by column separation to obtain compound (3-2). (5 g, 14.01 mmol, 63.09%). Preparation of Compound (9 6) Compound (96) (6 g) was obtained using Compound (3-2) in the same manner as the preparation of Compound (47) in Preparation 2. , 10.64 mmol, 75.08%). [Preparation Example 4] Preparation of Compound (102)

Preparation of Compound (4-1) 9H-Tribenzo[b,d,f]azepine (10 g, 41.10 mmol) was dissolved in THF (150 mL) and NBS (15.36 g, 86) 31 mmol) was added to the mixture. After mixing for 10 hours, distilled water was added. After extracting with EA and drying with water-free MgS? 4, it was distilled under reduced pressure, and then compound (4-1) (14 g, 34.90 mmol, 84.92%) was obtained by column separation. Preparation of Compound (4-2) Compound (4-2) (16 g, 25.30 mmol, 72.49 ° /) was obtained in the same manner as in the preparation of Compound (47). ). 31 94940 201111473 Preparation of Compound (102) Compound (4-2) (16 g, 25.30 ramol), phenyl linoleic acid (9.25 g, 75.90 mmol), Pd(PPh3)4 (1.46 g) , 1.26 mmol), 2MK2C〇3 (40 mL), toluene (200 mL) and ethanol (50 mL) were combined and stirred under reflux. After cooling at room temperature for 12 hours, distilled water was added. After extracting with EA and drying with anhydrous MgS 4 , the mixture was evaporated under reduced pressure, and then compound (102) (12 g, 19.14 mmol, 75.67%) was obtained by column separation. [Preparation Example 5] Preparation of Compound (109)

Preparation of compound (5-1) 9H-tribenzo[b,d,f]azepine (10 g, 41.10 mmol) was mixed with acetic acid (150 mL), and Bn (2.08 mL) was added. In the mixture. The mixture was stirred at 100 °C. After 5 hours, the mixture was cooled to room temperature and neutralized with aqueous NaOH. After extracting with EA and drying with anhydrous MgS 4 , and then distilling under reduced pressure, the compound (5-1) (9 g, 27.93 mmol, 68.12%) was obtained by column separation. Preparation of Compound (5-2) Compound (5-1) (9 g, 27.93 mmol), KOt-bu (4.7 g, 41.98 〇1) and 01^ (100 1111 〇 mixed with 150 ° (: stirring for 10 hours. The mixture was cooled to room temperature, distilled water was added. Extraction with EA and anhydrous 32 94940 201111473

After drying of MgS?4, it was distilled under reduced pressure, and then the compound (5-2) (8 g, 16.79 mmol, 60.12%) was obtained by column separation. Preparation of Compound (109) Compound (109) (5 g, 10.55 mmol, 62.88%) was obtained from Compound (5-2) in the same manner as the preparation of Compound (102). An organic electroluminescent compound (Compound 1 to Compound 128) was prepared in the same manner as in Preparation Examples 1 to 5. The NMR and MS/FAB data of the prepared organic electroluminescent compound are shown in Table 1. 33 94940 201111473 Table 1 Compound NMR (CDC13, 200 MHz) MS/FAB Measured value 1 δ = 6.69 (2H, πι), 6.87-6.92 (3H, m), 7.16 (2H, m), 7.41-7.54 ( 9H, m) , 7.62(1H, m) , 7.85(2H, m) , 7.99(1H, m) 396.48 396.16 3 δ = 6.69(2H, m> , 6· B7 (2H, m> , 7 · 16 ( 2H, m), 7,41~7·47(4Η,, 7·54~7·6(3Η, ra> , 7·78(1Η, m), 7.85(2H,m), 7.98~8.06(3H , m>, 8.13 (lH, m>, 8·44(1Η, m) 447.53 <147.17 4 δ = 6.69(2H, m) , 6.87-6.92(3H, m) , 7.16(2H, m) , 7.25 (4H, m), 7.41~7.54(9H, m), 7.62(1H, m), 7.85(2H, m), 7.99(1H, m) 472.58 472.19 7 δ = 6.69(2H, 6·87~6· 92(3Η, m>, 7.16~7.21(3H, m) f 7.41(2H, m), 7.51~7.54(10H,m) , 7.62(lH,m) , 7.76(lH,m> , 7.91(lHr m ), 7.99(1H, m) 472,58 472.19 12 δ = 6.69 (2H, m) , 6.76(1H, m), 6.87 (2H, m), 7.1S(2H,m) , 7.41~7.54(10H, Ro) , 7.66(lH,m), 7.79~7.8S(6H, m) , 8.33(1H, m) , 8.59(1H, s) 550.65 550.22 14 δ = 6.52 (1H, m) , 6.69(2Hf m) f 6.87 (2H, m), 7.16(2H, m), 7.41-7.54(12H, m), 7.82-7.85(3H, π〇, 8·3(2Η, m) 472.58 472.19 17 δ = 6.52 (1H, m> , 6·69(2Η, m> , 6.87(2Η, m> , 7.16<2H, m), 7.25(1H, m), 7.33(1H, m), 7.45~7.58(12H, m) , 7.69(1H, m>, 7.77-7.87(5H, m) r 7.94(1H, m) , 8.3(2H, m), 8.55(1H, m) 637.77 637.25 20 δ = 6.61 <1Η, m) 7 6.69 (2H, m) , 6.87-6.93(3Hf m) , 7.16(2H, m) , 7.25(1H, m> , 7.33(1H, m> , 7.47 (2H, m) , 7.54 (2H, m) 7 7.63-7,67 (4H, m), 7.85(2H, m), 7,93-7.94(2H, m) , 8.16(1H, m), 8.54~8.55(2H, m) 535,64 535,20 23 δ = 6.69(2H, m) , 6.87-6.92 (3H, m), 7.16(2H, m), 7.37-7.47 (15H, m) , 7.54~7·55 (5H , m), 7.61-7.62(3H, m) , 7.76(1H, m) # 7.85(2H, m), 7.99(1H, m) 654.87 654.25 24 δ = 6.69(2H, m) f 6.87(2H, m ), 7.16-7.18(3Hf m>, 7.41-7.54(9Hf m>, 7.85(4Η, m), 8.26-8.3 (3H, m) 473.57 473.19 30 δ = 6.69(2H, m) , 6.87(2H , m) , 7.16-7.18(3H, m), 7.3(2H, m) , 7.47(2H/ η) , 7.54(2H, m), 7.85(2H, m) f 8.15(2H, m); 8.26( 1H, m) 514.46 415.15 34 δ = 6.69(2H, m) , 6.87(2H, m) , 7.16-7.18(3H, m) , 7.37(6H, m) , 7.46-7.55(15H, m), 7.85~ 7.89 (4 H, m) , 8.26(1H, m) 655.86 655.24 38 δ = 6.69(2H, m) f 6.87 (2H, m) , 7.16-7.18(3H, m), 7.25-7.33 (3H, m) , 7.41 ( 1H, m), 7·5~7.54(5H, m), 7·63~7·64(2Η, m), 7.79-7.850H, m), 7.94(1H, in), 562.66 562.22 34 94940 201111473 8.12 -8.15 (2H7 m) , 8.26(^, m) , 8.55 (lHf m) 41 δ = 6.69(2H, m) , 6.87 (2H, m) , 7.16 (2H, m), 7·41(2Η, m&gt ; , 7,51~7.59(8H, m> , 7.79<4H, m> , 7.85(1H, s), 8(2H, m) , 8.4<2H, m) 523.63 523.20 46 δ = 6.69(2H , m> , 6· 87 (2H, m) , 7.16 (2H, m), 7.41(2H, m) ; 7.51-7.55(8H, m) , 7.79 (4H, m), 7.85<1H, s> , 8·01(1Η, m) , B.08~8.1<2H, m> , 8·55(1Η, 523.63 523.20 47 δ = 6.69(2H, m) , 6.87 (2H, m> , 7.16 (2H , m>, 7.41~7.54(10H,m), 7.79(4H,m>,7.B5(3H,s> 473.57 473.19 52 δ = 6.69(2H, m) r 6.87 (2Hf m) f 7.16(2H, m), 7,41-7.54 (14H, m), 7.85(7H, s), 8.3(4H, in) 625.76 625.25 54 δ = 6·69(2Η, ra) , 6.87 <2H, m) , 7.16 (2H, m), 7.41-7.57(18H, m) t 7.7-7.75(4H, m>, 7.85(3Hf s) 625.76 625.25 56 δ = 6.69 (2H, m>, 6.87 (2H, m>, 7.16 < 2H, m), 7.25 (lH, m >, 7.33 (lH, m >, 7.41 to 7.58 < 12H, m >, 7.69 (1H, m), 7.77~7.79<3H, m), 7.85(3H, s), 7.85-7.87<1H, m>, 7.94<1H, m>, 8.55(1H, m> 638.76 638.25 61 δ = 6.69 (2H, m) , 6.87(2H/ m) f 7.16 (2H, m) f 7.41-7.54 (14H, m) , 7.66(3H,m) , 1.85(2E, m), 9.02 (2H, m) 549.66 549.22 64 δ = 6.69(2H, m) , 6.87 (2H, m} r 7 · 16 (2H, m), 7.25~7.33(3H, m), 7.41-7.54(8H, m), 7·63~7 · 68 (3Η, m), 7.79~7·85 (6Η, m>, 7.94 (1H, m), 8.12 (1H, m), 8,55(^, m), 8.83(1H, s) 638.76 638.25 67 δ = 6.69 (2H, n〇, 6.78 (1H, m> , 6.87 <2H, m>, 7.16(2H, ro>, 7.25(1H, m>, 7.33(1H, 7.47(2H, m) , 7.54(2H, m) , 7.63-7.67(4H, m) f 7·85(2Η, m>, 7·94(1Η, m>, 8·16(1Η, ir〇, 8.54-8.55(3H, m ) 536·62 536.20 68 δ = 6.69(2Hf m) t 6.87 (2H, m) , 7.16-7.18(3H, m) , 7,37~7·47(15Η, m>, 7·54-7·55 (5H, m), 7.6K1H, m), 7.76 (1H, m), 7.85-7.89 (3H# m), 8.26(1H, m) 655.86 655.24 70 δ = 6·69(2Η, m> , 6.87(2H, m) , 7.16(2H, m> , 7.25(1H, m>, 7.33(1H, m)f 7.47(2H, m), 7.54(2H, m) , 7.63-7.67 (4H, m) , 7.85 (2H, m), 7.94 (1H, m), 8.16 (1H, m), 8.47 (2H, m), 8.54-8.55 (2H, m) 536,62 536.20 35 94940 201111473 73 δ = 6.69 (2H, m), 6.87(2Η, m) , 7.16(2Η, m), 7.41~7.54 (14Η, m> , 7.69(1Η,η) , 7.77 (2H,m), 7.85~7.87(3Η, m) , 8 (1Η, m), 8.18{1Η, m), 8.47 (2Η, m) 638.76 638.25 74 δ = 6.69(2Η, m), 6.87(2Η, η), 7.06(1Η, m), 7.16(2Η, m ), 7.31(1Η, m), 7.47(2Η, m), 7.54(2Η, m), 7.61(1Η, m), 7.85(2Η, m), Ί .92 (1Η, τη) , 8.06 (1Η, m) , 8.22 (1Η, πι> , 8.47 (2Η, m) 522.55 522.17 79 δ = 6.69(2Η, m) , 6.87(2Η, m) , 7.16-7.21(3Η, m) , 7.41(3Η, m) , 7.51~7.54(10Η, m), 7.76~7.79(5Η, m), 7.85(1Η, s), 7.91(1Η, m) 549.66 549.22 83 δ = 6.69~6.75(2Η, m) , 6.87(1Η, m) , 7.16(1Η, m) , 7.41 - 7.54 (16H, m) , 7.79 (4Η, m) , 7.85 (3Η, s) 549.66 549.22 85 δ = 6,75(2Η/ λ) , 7.25~7· 33<3Η, χη> , 7.41-7.51 (19Η, χη) , 7.58-7.63 (5Η fm) f 7·69≪1Η, m), 7·77~7·79<6Η, m> , 7'85<3Η, s), 7·85~7·87<1Η, m), 7·94~8 (2Η, m>, 8·12(1Η, m>, 8.18(1Η, α), 8.55(1Η, m) 956.14 955.37 89 δ = 6.S9(2H, m> , 6.87 (2Η, , 7.16 (2Η, π〇) , 7.41-7.54(10Η, m) , 7.85(2Η, m) , 8.28(4Η, m) 474.55 474.18 95 δ « 6·69(2Η, m〉Γ 6.87(2Η, m) , 7.16(2Η, m> , 7.25 (1Η, m) , 7.33(^, m) , 7.45-7.58 (9Η, m) f 7.69(1Η, a〇, 7.77(1Η, m> , 7.85-7.87(3Η, m> , 7.94(1Η , m), 8.28(1Η; s), 8.55(lHf m) 563.65 563.21 101 δ = 6.69 (2H, m) , 6.87 (2H, in) , 7.16 (2H, m), 7.37~7.47(15H, η) , 7.54-7.55 (5H, m), 7.61(1H, m) , 7.76(1H, πι) , 7.85 (2Η, in), 8.28(1Η, s), 8.38(1H, m) 656.85 656.24 103 δ = 6.69 (2H, m), 6.85(1H, s), 6.87(2H, m), 7.16 (2H, m), 7.41-7.54 (10H, in), 7.79-7.85(4H, m), 8.28(2H, m ) 473.57 473.19 110 δ = 6·06(1Η, m> , 6.69(2H, m> , 6.87 (2H, ία), 7.16 (2H, m) f 7.25-7.33 (3H, m) , 7.41 (1H, m ), 7.S-7.54(5H, m), 7.63-7.64(2H, m), 7.85(1H, m), 7.94(lHf m) , 8.08- 8.15(3H, m) , 8.28(2H, m), 8.55 (1H, m) , 562.66 562.22 115 δ = 6.4(2H, η) , 6.69(2H, m) , 6.87 (2H, m), 7.16(2H , m), 7.47(4H, , 7.54(6H, m>, 7.85(2R, m), 8.3(4H, m) 472.58 472.19 121 δ = 6.69(2H, m) , 6.85(1H, s) , 6.87 ( 2H, in), 7.16{2H, m), 7.41~7.54(10H, m), 7.79~7.85(4H, m), 8.28(2H, m) 473.57 473.19 36 94940 201111473 125 δ = 1.48(12»^ m > 1*73 (8H, m) , 2.72 (2Η, ία), 6.69(2Η, ΧΛ> '6·87(2Η, m) , 7.16(2Η, m), 7.36(4Η, βν) ^ 7 · 47(2Η, ») , 7.54 (2Η, m), 7 05(2Η, m) , 8.56(4Η, ιη) 638.84 638.34 126 δ = 6.69(2Η, ' 6*87 m) , 7.16~7.18(3Η , m), 7.25~7.33(3Η, η), 7.46~7·54(7Η, 7.63(1Η, η) , 7.79-7.85 (3Η, m) , 7.94(1Η, m), 8.09-8.12ί2Β^ / 8.26(1Η, ο) , 8.55(1Η, m) 562.66 562·22 127 δ β 6.69(2Η, ^ 6 87(2Η, λ), 7.16(2Η, m), 7.25~7.33<3Η/ »)/ 7.47~7.54(5Η, m), 7.63-7.6S(3H, m>, 7.79~7.85(4H, m>, 7.94UH, ®) / 8·12(1Η, m) , 8.28 (1Η, s), 8.55(1H, η) 563.65 563.21 128 δ = 6.69(2H, »), 6.78(1H, s> , 6.87(2H , m> , 7.16(2^/ 7.25-7.33(6H, m), 7.47-7.54» 7.63(2H, m) , 7.85(2H, m), 7.94(2H, 8.12(2H,.«0, 8.55( 2H, m) 651.76 651.24 [Example 1] Manufacture of an OLED device using an organic electroluminescent compound according to the present invention An OLED device was produced using the organic electroluminescent compound according to the present invention. First, a transparent electrode ΙΤ0 film (15 Ω / ΙΖΙ) prepared by using a glass substrate for OLED (Samsung Corning) was washed with a gas mixture of triethylene glycol, acetone, ethanol, and steaming water, and stored in isopropyl alcohol. spare. Then 'assemble the ΙΤ0 substrate into the substrate holder of the vacuum vapor deposition apparatus '4,4,,4"-parameter (N,N-(2-naphthyl)-phenylamino)triphenylamine (2 TNATA) And placing in a chamber of the vacuum vapor deposition apparatus, and then ventilating the chamber to a vacuum of 1〇-6 torr. Then, by applying a current to the chamber, the 2-TNATA is volatilized, thereby on the ΙΤ0 substrate. A hole injection layer having a thickness of 60 nm (nm) is formed thereon. Subsequently, n, N, ~ bis (<2_mercapto-diphenyl-4,4'-diamine (-) is placed thereon After the vacuum gas phase is used in another chamber of the device, NpB' is volatilized by applying a current to the chamber to form a hole transport layer having a thickness of 2 〇 nm on the hole injection layer. 94940 37 201111473 After the hole injection layer and the hole transport layer, an electric field light-emitting layer is formed thereon in the following manner. The compound (34) is placed in a chamber of a vacuum vapor deposition apparatus as a main body, and the compound Ir(PPy) of the following structure is used. 3) is placed in another chamber as a dopant. The two materials are evaporated at different rates' so that 4% to 10% by weight Vapor-deposited on the hole transport layer having a thickness of 3 0 ηπι the electroluminescent layer. 201111473

Compound 34 Ir (ppy) 3 Next, vapor-deposited bis(2-mercapto-8-hydroxyquinoline) (p-phenylphenol) aluminum (nI) (BAlq) with a thickness of 5 ηηη on the electroluminescent layer As a hole blocking layer, ginseng (8-hydroxyquinoline) aluminum (III) (Alq) having a thickness of 20 nm was vapor-deposited as an electron transport layer. Then, after vapor deposition of lithium quinolate (Liq) having a thickness of 1 (10) to 2 nm as an electron injecting layer, a vacuum vapor deposition apparatus was fabricated using another cathode (A1) to form a thickness of 15 〇 nm out of the OLED. . Hua will be purified. The compounds used in the OLED have been individually manufactured at 1 〇 6 t〇rr vacuum [Example 2] Manufacture of an OLED device using the organic electroluminescent compound of the present invention 94940 38 201111473 In addition to the hole barrier layer, Example 1 produced an OLED. [Example 3] Production of an OLED device using the organic electroluminescent compound of the present invention, except that the compound (41) and (piq) 2lr (acac) were used instead of the compound (34) and the dopant Ir(ppy) 3 according to the present invention. An OLED was fabricated in the same manner as in Example 2 except for the main body on the electroluminescent layer.

[Comparative Example 1] Electric field luminescence property of OLED using conventional electroluminescent material except that 4, 4'-N, Ν'-dicarbazole-biphenyl (CBP) was used instead of the compound according to the present invention in the vacuum vapor deposition apparatus An OLED was fabricated in the same manner as in Example 1 except that it was used as a host material in one of the cells. [Comparative Example 2] Electric field luminescence property of OLED using conventional electroluminescent material except that CBP was used instead of the compound according to the present invention as a host material in one of the chambers of the vacuum vapor deposition apparatus and BAlq was used as a hole barrier layer. An OLED was fabricated in the same manner as in Example 3. The luminous efficiency of the OLED device comprising the organic electroluminescent compound according to the present invention and the electroluminescent compound of 39 94940 201111473, which was produced in Examples 1 to 3 and Comparative Examples 1 and 2, was measured at 1,000 cd/m2. The results are shown in Table 2. Table 2 No. Main body dopant hole barrier driving voltage (V) @1,000 cd/m2 Power efficiency (lm/W) 01,000 Gd/ro2 Color Example 1 1 9 Ir (ppy) 3 BAlq 6.8 16.9 Green 2 14 Ir (ppy) a BAlq 6.6 17.5 Green 3 34 Ir (ppy) 3 BAlq 6.6 17.6 Green 4 52 Ir (ppy) a BAlq 6.7 16.7 Green 5 89 ir(ppy)3 HAlq 6.9 16.7 Green Example 2 1 23 Ir(ppy) a 6.6 16.6 Green 2 47 r r <ppy)3 - 6.2 17.9 Green 3 96 Ir(ppy)3 6.1 18.2 Green 4 103 Ir(ppy)3 - 6.2 18.1 Recording 5 127 Ir(ppy)3 - 6.3 17.6 Green Example 3 1 41 (piq) (acac) - 6.2 5.0 Red 2 46 (piq> 2 work r (acac> - 6.0 5.3 red 3 66 (piq) 2lr (acac> - 6.1 5.1 red 4 70 (piq> 2l3 : (acac) - 5.8 5.5 Red 5 97 (piq)2Ir (acac) - 5.9 5.3 Red Comparative Example 1 CBP Ir (ppy) 3 BAlg 7.5 10.5 Green Comparative Example 2 CBP (pi?) 2l^(^cac) BAlq · 7.5 2.6 Red As can be seen from Table 2, the organic electroluminescent compound according to the present invention has superior properties compared to conventional materials. Furthermore, the use of the organic electroluminescent compound according to the present invention is used. The device of the host material has excellent electric field illuminating properties and lowers the driving voltage, thereby increasing the power efficiency by 1. 7 to 3.2 lm/W and improving the power consumption. 40 94940 201111473 [Simple description of the figure] 】

Claims (1)

201111473 VII. Patent application scope: 1. An organic electric field luminescent compound represented by chemical formula (1): Chemical formula (1) A! to A3 independently denote CR or N, but excludes Αι to A3 as CR; Αιί and Ar2 independently represent hydrogen, (C6-C30) aryl with or without substituent, or with or without Substituent (C3-C30)heteroaryl; R and Ri to Ri2 independently represent hydrogen, gas, halogen, (C1-C30)alkyl group with or without a substituent, with or without a substituent (C6) -C30) aryl, substituted or unsubstituted (C6-C30) aryl group fused to one or more (C3-C30) cycloalkyl groups with or without a substituent, with or without a substituent a (C3-C30)heteroaryl group, a 5- to 7-membered heterocycloalkyl group having or without a substituent, and a 5- to 7-membered fused with one or more aromatic rings having or without a substituent a cycloalkyl group, a (C3-C30) cycloalkyl group having or not having a substituent, a (C3-C30) cycloalkyl group fused to one or more aromatic rings having or not having a substituent, a cyano group, a succinyl group , NR21R22, BR23R24, PR25R26, P(=0)R27R28 [wherein R21 to R28 are independently represented by (n-C30) alkane with or without a substituent 42 94940 201111473, with or without a (C6-C30) aryl group of a substituent or a (C3-C30)heteroaryl group with or without a substituent], R29R3〇R3iSi_ [wherein R29 to R31 are independently represented by a group having or without a substituent (C1-C30) (C6-C30) aryl group with or without a substituent (C3-C30)heteroaryl group with or without a substituent, (C6-C30) aryl group with or without a substituent (C1-C30)alkyl, R32X-[wherein X represents S or 0, and R32 represents (C1-C30)alkyl with or without a substituent, with or without a substituent (C6-C30) An aryl group (C3-C30)heteroaryl group with or without a substituent, a (C2-C30) alkenyl group with or without a substituent, a (C2-C30) alkynyl group with or without a substituent, Or R and Ri to R12 may be bonded to an adjacent substituent via a (C3-C30)alkylene group or a (C3-C30)alkylene group with or without a fused ring to form an alicyclic ring, a single ring or more An aromatic ring of a ring or a heterocyclic ring of a single or multiple ring; the W system is not _(CR5lR52)m_, _(R51)C = C.(R52)-, _N(R53)-, _S_, _0_, _Si( R54) (R55)_, _P(R56)_, _P(=0)(R57)-, -C(=0)_ or -B(R58)-; R4I to R43 and R5I to R58 and Rl to Rl2 The same; the heterocycloalkyl or heteroaryl group may contain one or more heteroatoms selected from B, N, 0, S, P (=0), Si, and P; and the m system represents an integer of 0, 1, or 2. . 2. The organic electroluminescent compound according to claim 1, wherein the substituents of An, An, R, R! to R12, R21 to R32, r41 to r43 and the core to R58 may be further in 43 94940 201111473. Substituted by one or more substituents selected from the group consisting of hydrazine, il, (C1-C30)alkyl with or without a _ substituent, (C6-C30) aryl, with or without a (C3-C30)heteroaryl group having a (C6-C30) aryl substituent, a 5- to 7-membered heterocycloalkyl group, a 5- to 7-membered heterocycloalkyl group fused to one or more aromatic rings, (C3-C30) cycloalkyl, fused to one or more aromatic rings (C6-(di)decylcycloalkyl, RaRbRcSi-[wherein, R, RC are independently represented by (cl_c3〇) alkyl or (C6- C30) aryl MC2-C30) alkenyl, (C2_C3 fluorene) alkynyl, cyano, oxazolyl, NRdRe, BRfR6, PR%, p(=〇)RjRk [its ^1^ to Rk are independently represented (C1 -C30)alkyl, (C6_C3())aryl or (C3-C30)heteroaryl], (C6-C30)aryl (c-C3〇)alkyl, (CK30)alkyl (C6-C30) Aryl, hydrazine [where lanthanide represents s or yttrium, R1 ray (GD filament, (C6-C3G) filament or (C3_C3 〇) Square group], r(c=〇)-[wherein Rra represents (C1_(10) appearance group, (C1-C3Q) alkoxy group, ((3)-(10) aryl or (10)) aryloxy group), yl group, dioxane 3 a group, a (C6W0) aryl group or a (C6_C30) aryloxy group, a carboxyl group, a nitro group, and a hydroxyl group; or a bond with an adjacent substituent to form a ring. a compound whose 'when h to _ is linked to an adjacent substituent by an extension or extension Is selected from the following structures: 94940 44 201111473 Wherein R1, R3, R4, R5, R7, L, R9, R1Q, Rn and R12 are independently hydrogen, aryl, dentate, (6)-c3 fluorene with or without substituents, with or without A (10)-(10) aryl group having a substituent or a (C3-C30) heteroaryl group having or not having a substituent. 4. The organic electroluminescent compound according to the invention of claim 4, wherein Wherein, Αιί and An are independently represented by hydrogen, (C6-C30)aryl having or without a substituent or (C3_C3〇)heteroaryl having or without a substituent. 5. The organic electric field hair-emitting compound as described in the sf patent scope, wherein 'R! to R12 series independently represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutylene. Base, tert-butyl, pentyl, pentyl, hexyl, heptyl, octyl, decyl, decyl, fluoro, chloro, molybdenyl, phenyl, bergyl, 2-naphthyl, N-carbazolyl , phenyl-indole-carbazolyl, N-phenyl-2-oxazole 94940 45 201111473, N-phenyl-3-oxazolyl, fluorenyl-phenyl-4-oxazolyl, 2-pyridine , 3-pyridyl, 4-pyridyl, quinolyl, 6-quinoxalinyl, buptiyl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl or 9-phenanthryl; and R, An and Arz independently represent hydrogen, phenyl, naphthyl, 2-naphthyl, biphenyl, 2-quinolyl, 3-quinolyl, 4-quinolyl, 5-quinolinyl, 6-quinoline , 7-quinolyl, 8-quinolyl, 9H_S_2-yl, 9H-indol-3-yl, 9H-g-4-yl, 9H-S-1-yl, N-carbazolyl, phenyl -1-oxazolyl, N-phenyl-2-oxazolyl, N-phenyl-3-oxazolyl, N-phenyl-4-oxazolyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyridyl, 3-pyridyl, 4- Pyridyl, 1,2,3-trimorph-4-yl, l2,3-three tillage, indole, 3,5-trin-2-yl, N-7H-benzo[c]carbazolyl, N-phenyl-7H-benzo[c]carbazole-i〇-yl, N_phenyl-7H_ benzo[c]carbazole-11-yl, N_phenyl-7H_benzo[c] Carbazole -9-yl, N-phenyl-7H- benzo[c]carbazole-8-yl, 1-indenyl, 2-phenylene, 3-indole, 5-mercapto, 6 - 吲耕基, 7_ morphine, 8_mercapto, 6-phenyl and coughyl, 7-dibenzofuranyl, 8-dibenzopyranyl, 9- and D-fu Base, dibenzocyclopentaborin-6-yl, dibenzocyclopentane-7-yl, dibenzocyclopentaborane _8-yl, dibenzocyclopentaborane α, 3-isoindolyl, 1-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 8-isoquinolyl Or Ν-pyrido[2,3-b]fluorenyl, and the phenyl, naphthyl, biphenyl, quinolyl, indolyl, phenanthryl, acridinyl, 94940 46 of r, Ari and Αη 201111473 Dimercapto, quinolyl, pyrimidinyl, fluorenyl, oroxazolyl or N_7H-benzo[Z]carbazolyl may be further substituted with one or more substituents selected from the group consisting of methyl and benzene. Base, triphenylsulfanyl, trimethylsulfonyl, N-carbazolyl, cyano, fluoro, methoxy, trifluoromethyl and cyclohexyl. An organic electric field illuminating device according to any one of claims 1 to 5, which is an organic electroluminescent device. 7. The organic electroluminescent device of claim 6, comprising a first electrode; a second electrode; and one or more organic layers interposed between the first electrode and the second electrode; The organic layer comprises one or more organic electroluminescent compounds according to any one of claims 5 to 5, and one or more dopants represented by the chemical formula (3): Chemical formula (3) MiL101L102L103 (3) wherein, Μ a metal selected from the group consisting of: Group 7, Group VIII, Group 9, Group 10, Group 11, Group 13, Group 14, Group 15, and Group 16, and With a ligand, Ll. 2 and are independently selected from the following structures: 47 94940 201111473 Wherein R201 to R2G3 independently represent hydrogen (C1-C30)alkyl group with or without a halogen substituent, (C6-C30) aryl group with or without (C1-C30) alkyl substituent, or halogen ; R204 to R21 9 are independently represented by hydrogen, (C1-C30)alkyl group with or without a substituent, (C1-C30) alkoxy group with or without a substituent, 48 94940 201111473, with or without a substituent (C3_C3〇)cycloalkyl, (C2-C30)alkenyl group with or without a substituent, (C6-C3G)aryl group with or without a substituent, single or two with or without a substituent ( Cl_C3〇) alkylamino group, mono- or di(C6_C3〇)arylamino group with or without a substituent, SFs, tri(C1-C30)alkyldecane group with or without a substituent, with or without a substituted (cl_C3〇)alkyl (C6_C3〇) arylalkylene group, a tris(C6_C3〇) aryl phenyl group with or without a substituent, a cyano group or a γ element; R22◦ to Rm are independent (C1-C30)alkyl group with or without a halogen substituent (C6-C3) with or without a (cl_C3〇)alkyl substituent 0) aryl; R224 and R225 are independently represented by hydrogen, (C1-C30)alkyl group with or without a substituent, (C6_C3〇) aryl group with or without a substituent, or halogen, or Rm and R225 may be used. An alicyclic ring, or a monocyclic or polycyclic aromatic ring, is bonded via a (C3-C12)alkylene group or a (C3-C12)alkylene group with or without a fused ring; R226 means with or without a (cl_C3〇)alkyl group 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 a functional group; R227 to R229 (C1-C30)alkyl independently, with or without a substituent, (C6_C3〇)aryl, or with or without a substituent; and 94940 49 201111473 «231 R232 R2WR238^R2« (d) means ' ΊΎ, wherein, ^ to "Chengdu hydrogen, with or without (tetra) substituent = C30) alkyl, (6) alkoxy, south, with or without, based (C6-C3G) , cyano group, or with or without a substituent C5 C30) ^ burnt base ' or R231 to the core 2 can be individually extended by stretching, reductive and adjacent Bonding to form a spiro ring or a fused ring, or two to singly form a saturated or unsaturated fused ring via a (tetra) or an alkenyl group and an R24-bonding δ. The organic electric field luminescence described in claim 7 The device, the pot and the organic layer further comprise one or more amine compounds selected from the group consisting of arylamine compounds of the vinyl arylamine compound or a plurality of metals selected from the group consisting of: Group 1 There are 9 series metals and transition elements of the 2nd, 4th, and 5th cycles.斓 . ^ The organic electric field illumination described in claim 7 of the patent application, wherein the organic layer comprises an electric field luminescent layer and a charge generating layer. The electric field illuminating device of the stepper machine, wherein the organic layer is an organic electric field that emits two layers or multiple layers of blue light, red light or green light. 94940 50 201111473 IV. Designated representative figure: No case in this case (1) The specified representative map is: the () graph. (2) A brief description of the symbol of the representative figure: 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: 2 94940 201111473 , No., 9912^76 (^1 fan V please * cable -: (not known as iof厶) R41 to R43 and R51 to R58 are the same as R! to R12; ,,..." The heterocycloalkyl or The heteroaryl group may contain one or more heteroatoms selected from the group consisting of ruthenium, osmium, 0, S, P (=〇), Si, and P; and the m system represents an integer of 0, 1, or 2. The structure is exemplified independently. Wherein R43 and R51 to R58 independently represent a (C1-C30)alkyl group having a substituent j (C1-C30) alkyl group, a (C6_c3〇) aryl group having or not having a substituent, and Wu f with or without a substituent ( G3_(10))heteroaryl, or ^ and r51j, may be bonded by a ((3)(10))extended (tetra)=3-C30)alkenyl group with an adjacent ring to form an alicyclic ring. A ring or a polycyclic aromatic ring or a monocyclic or polycyclic heteroaryl ring. [Embodiment] In the present invention, the substituents of the alkyl group, the "alkoxy group," and other "European 94940 modified version 9 201111473 base" portions include both a straight chain and a branched chain. "Aryl" means an organic radical derived from the removal of a hydrogen atom from an aromatic hydrocarbon and may include from 4 to 7 members, especially a single or fused ring of 5 or 6 members, including a plurality of single bonds. Linked aryl groups. Specific examples include phenyl, naphthyl, biphenyl, anthracenyl, fluorenyl, fluorenyl, phenanthryl, tertylpheny 1 eny 1 (chrysenyl), condensed tetraphenyl (naphthacenyl), propylene, fluoranthenyl, etc., but is not limited thereto. The naphthyl group includes 1-naphthyl and 2-naphthyl groups, and the fluorenyl group includes 1-mercapto and 2-indenyl groups. And a 9-fluorenyl group, and the anthracene group includes a 1-position, a 2-indenyl group, a 3-position group, a 4-anthrace group and a 9-fluorenyl group. In the present invention, "heteroaryl group" means One to four hetero atoms selected from B, N, 0, S, P (=0), Si, and P as an aromatic ring skeleton atom and an aryl group as a carbon atom of the remaining aromatic ring skeleton atom . The heteroaryl group may be a 5- or 6-membered monocyclic heteroaryl group or may be obtained by condensation with a benzene ring, a heteroaryl group, and may be partially saturated. Further, the heteroaryl group includes more than one heteroaryl group linked by a single bond. The heteroaryl group includes a divalent aryl group in which a hetero atom in the ring can be oxidized or ceometrically formed such as an N- or quaternary salt. Specific examples include monocyclic heteroarylthiophenyl, pyrrole I k ^ 丞 丞, imidazolyl, pyrazolyl, π oxazolyl, oxadiazolyl, fluorenyl L-based, filamentary, Salivation, two-base, sigma, and sigma sit on its morphine-derived meso-based, furazolidyl, pyridyl, pyridyl, pyrimidinyl, hetero-cyclohexa-heteroaryl, such as benzo-alpha Benzyl, benzoisoyl, benzopyrene, benzo(tetra)yl, benzoisoyl, /, 3 oxazolyl, benzoxazolyl, isodecyl, fluorenyl, carbazolyl, 94940 10 201111473 Patent Application No. 99123760 (October 10, 1999) based on (C3-C30) heteroaryl. It is selected from the following structures, but is not limited to this: Wherein R, An and An each independently represent fluorene, f% u (C6-C30) aryl group with or without a substituent or (C3-C30) heteroaryl group with or without a substituent.匕 to R12 independently represent hydrogen, fluorenyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, pentyl, pentyl, hexyl, heptyl, octyl, fluorene Base, fluorenyl, fluoro, chloro, bromo, phenyl, 1-naphthyl, 2-naphthyl, Ν-σ卡β, N-phenyl_1_π卡σ, N_phenyl-2- taste. Sitting group, N_phenyl -3_σ card β-based, Ν'-phenyl-4-flavor. Sitting group, 2_° ratio biting group, 3-ntbw group, 4-吼^定基,喧# base, 6-喧曜, 1, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, ❹4-phenanthryl Or 9-phenanthryl; R, An and An are independently represented by argon, phenyl, naphthyl, 2-naphthyl, biphenyl, 2-mercapto, 3-indole, 4-mercapto, 5-喧淋基,6-啥淋基,7-喧琳基,8-喧琳基,9H-苐-2-yl, 9H-indol-3-yl, 9H-^-4-yl, 9H-荞- P, N-hydrazinyl, N-phenyl-oxazolyl, N-phenyl-2-oxazolyl, N-phenyl-3-oxazolyl, N-phenyl-4-carbazole Base, 2-σ dense η base, 4-β dense base, 5-^σ base, 2-π ratio π base, 3-π ratio bite base, 4-π ratio β base, 1, 2, 3-three哄-4-yl, 1,2,3-tris-5-yl, 1,3,5-trin-2-yl, Ν-7Η-benzo[c]carbazolyl, fluorenyl-phenyl- 7Η-benzo[c]咔13 94940 revision 201111473 Patent application No. 99123760 (99 years 1 month & 曰 ° sitting -10- base, phenyl-7H-benzo[〇] ° card. Sitting - Η-based, N-phenyl-7h_benzo[c]^e-s--9-yl, N-phenyl-7H-benzo[c]pyranyl, indolyzynyl, 2-吲哄, 3-吲哄, 5-3|D well Base, 6-fluorenyl, 7-fluorenyl, 8-hydrazine, 6, dibenzofuranyl, 7-dibenzofuranyl, 8-dibenzofuranyl, 9-dibenzofuran Dibenzoborolan-6-yl (dibenzoboro b-6-yl), dibenzocyclopentaborane mono-, dibenzocycloborane-8-yl, di-p-cyclopentanyl Borane-9-yl, , 3-isoline-based, 1-isoline-based, 4-isolated.奎琳基, 5__ = quinolinyl, 6-isoquinolyl, 7-isoquinolinyl, 8-isoquinolinyl or N-pyridyl Bil[, 2'3~b]^, and R, The phenyl group, the naphthyl group, the fluorene group, the fluorenyl group, the phenanthryl group of red 1 and Αη. ratio.疋基,二哄基,啥琳基, .'基吲π井基,Ν-味-salt or Ν-7Η-benzo[c]-salt-salt can be selected as one of the following or Substituted by a plurality of substituents: methyl, phenyl, di-based, fluorenyl-indole, trimethylsulfanyl, fluorenyl-carbazolyl, cyano, fluoro, methoxy, trifluoromethyl and cyclic Heji. In particular, the organic electroluminescent compound according to the present invention has the following structures, but is not limited thereto. 94940 revision 14 201111473 94940 19 201111473 Patent application No. 99123760 ("Day of October; The organic electroluminescent compound according to the present invention can be prepared by the following reaction scheme (1): Reaction scheme (1) In the reaction scheme (1), Ai to As, An, Ar2 and L to I Α t Rl2 are defined in the formula (1) and the phase 94940 is revised. 20 Patent No. 99123760 蜣 (" October 1st) 201111473 t Same as. Provided is an organic electric field light-emitting device according to the present invention, comprising: a first electrode; a second electrode; and one or more organic layers interposed between the first electrode and the second electrode; wherein the organic layer One or more organic electroluminescent compounds represented by the chemical formula (1) are contained. The organic layer comprises an organic electroluminescent layer comprising one or more dopants and one or more organic electroluminescent compounds of the formula (1) as a host. The dopant to be applied to the organic electroluminescence device of the present invention is not particularly limited, and is preferably selected from the compounds represented by the following chemical formula (3). Formula (3) wherein M1 is selected from the group consisting of metals of Group 7, Group 8, Group 9, Group 10, Group 11, Group 13, Group 14, Group 15 and The metal of Group 16 and the ligands Lm, L1()2 and L1()3 are independently selected from the following structures: 21 94940 Rev. 201111473 R205 R218 ^22i R2IB R213 Wherein, R6〇3 is independently represented by hydrogen, (C1-C30)alkyl having or without a halogen substituent, (C6-C30) aryl having or not having (C1-C30)alkyl substituent Or i; Rm to R219 independently represent hydrogen, with or without substituents 22 94940