EP2697216A1 - Novel compounds for organic electronic material and organic electroluminescent device using the same - Google Patents

Novel compounds for organic electronic material and organic electroluminescent device using the same

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Publication number
EP2697216A1
EP2697216A1 EP12771699.1A EP12771699A EP2697216A1 EP 2697216 A1 EP2697216 A1 EP 2697216A1 EP 12771699 A EP12771699 A EP 12771699A EP 2697216 A1 EP2697216 A1 EP 2697216A1
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EP
European Patent Office
Prior art keywords
group
substituted
unsubstituted
compound
aryl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Application number
EP12771699.1A
Other languages
German (de)
French (fr)
Other versions
EP2697216A4 (en
Inventor
Hee-Choon Ahn
Seok-Keun Yoon
Hee-Sook Kim
Soo-Jin Yang
Kyung-Joo Lee
Nam-Kyun Kim
Young-Jun Cho
Hyuck-Joo Kwon
Bong-Ok Kim
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
DuPont Specialty Materials Korea Ltd
Original Assignee
Rohm and Haas Electronic Materials Korea Ltd
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Application filed by Rohm and Haas Electronic Materials Korea Ltd filed Critical Rohm and Haas Electronic Materials Korea Ltd
Publication of EP2697216A1 publication Critical patent/EP2697216A1/en
Publication of EP2697216A4 publication Critical patent/EP2697216A4/en
Withdrawn legal-status Critical Current

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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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    • C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
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    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C07F7/0814—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring said ring is substituted at a C ring atom by Si
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    • H05B33/00—Electroluminescent light sources
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    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
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    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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    • Y02B20/00—Energy efficient lighting technologies, e.g. halogen lamps or gas discharge lamps

Definitions

  • the present invention relates to novel compounds for organic electronic material and an organic electroluminescent device using the same.
  • An electroluminescent (EL) device is a self-light-emitting device which has advantages over other types of display devices in that it provides a wider viewing angle, a greater contrast ratio, and has a faster response time.
  • An organic EL device was first developed by Eastman Kodak, by using small molecules which are aromatic diamines, and aluminum complexes as a material for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
  • Iridium(III) complexes have been widely known as phosphorescent materials, including bis(2-(2’-benzothienyl)-pyridinato-N,C3’)iridium(acetylacetonate) ((acac)Ir(btp) 2 ), tris(2-phenylpyridine)iridium (Ir(ppy) 3 ) and bis(4,6-difluorophenylpyridinato-N,C2)picolinate iridium (Firpic) as red, green and blue materials, respectively.
  • 4,4’-N,N’-dicarbazol-biphenyl (CBP) is the most widely known host material for phosphorescent substances.
  • WO 2006/049013 discloses compounds for organic electroluminescent materials having a condensed bicyclic group as a backbone structure. However, it does not disclose a compound having a nitrogen-containing condensed bicyclic group, a carbazole group which is substituted with an aromatic ring-fused cycloalkyl or heterocycloalkyl group at each of the 3- and 9- positions, and an aromatic ring-fused heterocycloalkyl or cycloalkyl group.
  • the objective of the present invention is to provide a compound for organic electronic material, which has an excellent structure imparting high luminous efficiency and a long operation lifetime to a device, and having proper color coordination; and an organic electroluminescent device, which has high efficiency and a long lifetime, using said compounds.
  • L1 and L2 each independently represent a single bond, a substituted or unsubstituted 5- to 30-membered heteroarylene group, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (C6-C30)cycloalkylene group;
  • X1 represents CH or N
  • Y1 and Y2 each independently represent -O-, -S-, -CR 8 R 9 - or -NR1 0 -;
  • R1 to R 10 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted 5- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group fused with at least one (C3-C30)cycloalkyl group, a 5- to 7-membered heterocycloalkyl group fused with at least one substituted or unsubstituted (C6-C30)aromatic ring
  • R 21 to R 27 have the same definition as one of R1 to R 10 ;
  • a, b, e and g each independently represent an integer of 1 to 4; where a, b, e or g is an integer of 2 or more, each of R1, each of R 2 , each of R 5 or each of R 7 is the same or different;
  • c, d and f each independently represent an integer of 1 to 3; where c, d or f is an integer of 2 or more, each of R 3 , each of R 4 , or each of R 6 is the same or different; and
  • the compounds for organic electronic material according to the present invention can manufacture an organic electroluminescent device which has high luminous efficiency and a long operation lifetime.
  • the present invention relates to a compound for organic electronic material represented by the above formula 1 and an organic electroluminescent device comprising the compound.
  • (C1-C30)alkyl(ene) is meant to be a linear or branched alkyl(ene) having 1 to 30 carbon atoms, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.;
  • (C2-C30) alkenyl(ene) is meant to be a linear or branched alkenyl(ene) having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.
  • “(C2-C30)alkynyl” is a linear or branched alkynyl having 2 to
  • substituted in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or group, i.e., a substituent.
  • R1 to R 10 and R 21 to R 27 groups are each independently at least one selected from the group consisting of deuterium, a halogen, a (C1-C30)alkyl substituted or unsubstituted with a halogen, a (C6-C30)aryl, a 5- to 30-membered heteroaryl substitute
  • L1 and L2 each independently are preferably a single bond, a substituted or unsubstituted 5- to 21-membered heteroarylene group, a substituted or unsubstituted (C6-C20)arylene group, or a substituted or unsubstituted (C6-C20)cycloarylene group, more preferably one selected from group consisting of a single bond, phenylene, naphthylene, biphenylene, terphenylene, anthrylene, andenylene, fluorenylene, phenanthrylene, triphenylenylene, pyrenylene, phenylenylene, chrysenylene, naphthasenylene, fluorantenyl, furylene, thiophenylene, pyrrolylene, imidazolylene, pyrazolylene, thiazolylene, thiadiazolylene, isothiazolylene, isoxazolylene, ox
  • Y1 and Y2 each independently represent -O-, -S-, -CR 8 R 9 - or -NR 10 -, wherein R 8 and R 9 preferably each independently a substituted or unsubstituted (C1-C30)alkyl group or a substituted or unsubstituted (C6-C30)aryl group, or are linked to an adjacent substituent via a substituted or unsubstituted (C3-C30)alkylene or a (C3-C30)alkenylene group to form a mono- or polycyclic, alicyclic or aromatic ring, more preferably each independently represent an unsubstituted (C1-C10)alkyl group or an unsubstituted (C6-C12)aryl group, or are linked to an adjacent substituent to form a mono- or polycyclic, (C1-C10)alicyclic or (C6-C15)aromatic ring.
  • R 10 preferably represents a substituted or unsubstituted (C6-C30)aryl group or a substituted or unsubstituted 3- to 30-membered heteroaryl group, more preferably represents a (C6-C20)aryl group unsubstituted or substituted with deuterium, a halogen, a (C1-C6)alkyl or a (C6-C12)aryl, or a 5- to 21-membered heteroaryl group substituted with a (C6-C12)aryl.
  • R1 to R 7 preferably each independently represent hydrogen, a substituted or unsubstituted (C6-C30)aryl group or -SiR 23 R 24 R 25 , or are linked to an adjacent substituent via a substituted or unsubstituted (C3-C30)alkylene or a (C3-C30)alkenylene group to form a mono- or polycyclic, alicyclic or aromatic ring, more preferably each independently represent hydrogen, an unsubstituted (C6-C12)aryl group or -SiR 23 R 24 R 25 , or are linked to an adjacent substituent to form a mono- or polycyclic (C6-C12)aromatic ring.
  • the representative compounds of the present invention include the following compounds:
  • the compounds for organic electronic materials according to the present invention can be prepared according to the following reaction scheme.
  • R1 to R 7 , Y1 and Y2, X1, L1 and L2, a, b, c, d, e, f and g are as defined in formula 1 above, and X represents a halogen.
  • the present invention provides an organic electroluminescent device comprising the compound of formula 1.
  • Said organic electroluminescent device comprises a first electrode, a second electrode, and at least one organic layer between said first and second electrodes.
  • Said organic layer comprises at least one compound of formula 1 according to the present invention.
  • said organic layer comprises a light-emitting layer in which the compound of formula 1 is comprised as a host material.
  • a phosphorescent dopant which is used for an organic electroluminescent device together with the host material according to the present invention, may be selected from compounds represented by the following formula 2:
  • L 101 , L 102 and L 103 are each independently selected from the following structures:
  • R 201 to R 203 each independently represent hydrogen, deuterium, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), a (C6-C30)aryl group unsubstituted or substituted with (C1-C30)alkyl group(s), or a halogen;
  • R 204 to R 219 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, SF 5 , a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)aryl
  • R 220 to R 223 each independently represent hydrogen, deuterium, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), or a (C6-C30)aryl group unsubstituted or substituted with (C1-C30)alkyl group(s);
  • R 224 and R 225 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a halogen, or R 224 and R 225 may be linked to each other via a (C3-C12)alkylene group or (C3-C12)alkenylene group with or without a fused ring, to form a mono- or polycyclic, alicyclic or aromatic ring;
  • R 226 represents a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 5- or 30-membered heteroaryl group or a halogen;
  • R 227 to R 229 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group or a halogen;
  • R 231 to R 242 each independently represent hydrogen, deuterium, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), a (C1-C30)alkoxy group, a halogen, a substituted or unsubstituted (C6-C30)aryl group, a cyano group, or a substituted or unsubstituted (C5-C30)cycloalkyl group, or each of R 231 to R 242 may be linked to an adjacent substituent via (C2-C30)alkylene group or (C2-C30)alkenylene group to form a spiro ring or a fused ring or may be linked to R 207 or R 208 via a (C2-C30)alkylene group or (C2-C30)alkenylene group to form a saturated or unsaturated fused ring.
  • the dopants of formula 2 include the following, but are not limited thereto:
  • the organic electroluminescent device according to the present invention may further comprise, in addition to the compounds represented by formula 1, at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.
  • the organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4 th period, transition metals of the 5 th period, lanthanides and organic metals of d-transition elements of the Periodic Table, or at least one complex compound comprising said metal.
  • the organic layer may comprise a light-emitting layer and a charge generating layer.
  • the organic electroluminescent device may emit a white light by further comprising at least one light-emitting layer which comprises a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound, in addition to said organic layer comprising the compound according to the present invention.
  • a surface layer selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on an inner surface(s) of one or both electrode(s).
  • a chalcogenide(includes oxides) layer of silicon or aluminum is placed on an anode surface of an electroluminescent medium layer, and a metal halide layer or metal oxide layer is placed on a cathode surface of an electroluminescent medium layer.
  • Such a surface layer provides operation stability for the organic electroluminescent device.
  • said chalcogenide includes SiO X (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, etc.; said metal halide includes LiF, MgF 2 , CaF 2 , a rare earth metal fluoride, etc.; and said metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO, etc.
  • a mixed region of an electron transport compound and an reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes.
  • the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transpor electrons from the mixed region to an electroluminescent medium.
  • the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium.
  • the oxidative dopant includes various Lewis acids and acceptor compounds; and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
  • a reductive dopant layer may be employed as a charge generating layer to prepare an electroluminescent device having two or more electroluminescent layers and emitting a white light.
  • Example 1 Production of an OLED device using the compound according to the present invention
  • OLED device was produced using the compound according to the present invention.
  • a transparent electrode indium tin oxide (ITO) thin film (15 ⁇ /sq) on a glass substrate for an organic light-emitting diode (OLED) device (Samsung Corning, Republic of Korea) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and then was stored in isopropanol. Then, the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus.
  • N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine was introduced into a cell of said vacuum vapor depositing apparatus, and then the pressure in the chamber of said apparatus was controlled to 10 -6 torr. Thereafter, an electric current was applied to the cell to evaporate the above introduced material, thereby forming a hole injection layer having a thickness of 60nm on the ITO substrate.
  • N,N’-di(4-biphenyl)-N,N’-di(4-biphenyl)-4,4’-diaminobiphenyl was introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying electric current to the cell, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
  • compound C-2 was introduced into one cell of the vacuum vapor depositing apparatus, as a host material
  • compound D-11 was introduced into another cell as a dopant.
  • the two materials were evaporated at different rates and were deposited in a doping amount of 4 to 20wt% to form a light-emitting layer having a thickness of 30 nm on the hole transport layer.
  • the produced OLED device showed red emission having a luminance of 1,020cd/m 2 and a current density of 14.0mA/cm 2 at a driving voltage of 4.0V. Further, the minimum time taken to be reduced to 90% of the luminance at a luminance of 5,000nit was 60 hours.
  • Example 2 to 11 Production of an OLED device using the compound according to the present invention
  • An OLED device was produced in the same manner as one of Example 1, except for using those shown in the below Table as a host material and a dopant.
  • Comparative Example 1 Production of an OLED device using conventional electroluminescent compounds
  • An OLED device was produced in the same manner as that of Example 1, except that a light-emitting layer having a thickness of 30 nm was deposited on the hole transport layer by using 4,4’-N,N’-dicarbazol-biphenyl (CBP) as a host material and compound D-11 as a dopant and that a hole blocking layer having a thickness of 10 nm was deposited by using aluminum(III) bis(2-methyl-8-quinolinato)-4-phenylphenolate.
  • CBP 4,4’-N,N’-dicarbazol-biphenyl
  • the produced OLED device showed red emission having a luminance of 1,000cd/m 2 and a current density of 20.0mA/cm 2 at a driving voltage of 8.2V. Further, the minimum time taken to be reduced to 90% of the luminance at a luminance of 5,000nit was 10 hours.
  • the compounds of the present invention have superior luminescent properties than the conventional materials. Further, the device using the compounds according to the present invention as a host material induces an increase in power efficiency by reducing a driving voltage, and thus can improve power consumption.

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Abstract

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

Description

    NOVEL COMPOUNDS FOR ORGANIC ELECTRONIC MATERIAL AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME
  • The present invention relates to novel compounds for organic electronic material and an organic electroluminescent device using the same.
    •
  • An electroluminescent (EL) device is a self-light-emitting device which has advantages over other types of display devices in that it provides a wider viewing angle, a greater contrast ratio, and has a faster response time. An organic EL device was first developed by Eastman Kodak, by using small molecules which are aromatic diamines, and aluminum complexes as a material for forming a light-emitting layer [Appl. Phys. Lett. 51, 913, 1987].
  • The most important factor to determine luminous efficiency in an organic EL device is a light-emitting material. Until now, fluorescent materials have been widely used as a light-emitting material. However, in view of electroluminescent mechanisms, phosphorescent materials theoretically show four (4) times higher luminous efficiency than fluorescent materials. Thus, recently, phosphorescent materials have been investigated. Iridium(III) complexes have been widely known as phosphorescent materials, including bis(2-(2’-benzothienyl)-pyridinato-N,C3’)iridium(acetylacetonate) ((acac)Ir(btp)2), tris(2-phenylpyridine)iridium (Ir(ppy)3) and bis(4,6-difluorophenylpyridinato-N,C2)picolinate iridium (Firpic) as red, green and blue materials, respectively. At present, 4,4’-N,N’-dicarbazol-biphenyl (CBP) is the most widely known host material for phosphorescent substances. Further, Pioneer (Japan) et al. developed a high performance organic EL device employing, as a host material, bathocuproine (BCP) and aluminum(III)bis(2-methyl-8-quinolinate)(4-phenylphenolate) (BAlq) which had been a material used for a hole blocking layer.
  • Though these phosphorous host materials provide good light-emitting characteristics, they have the following disadvantages: (1) Due to their low glass transition temperature and poor thermal stability, their degradation may occur during a high-temperature deposition process in a vacuum. (2) The power efficiency of an organic EL device is given by [(π/voltage) × current efficiency], and the power efficiency is inversely proportional to the voltage, and thus the power efficiency should be high in order to reduce power consumption. Although an organic EL device comprising phosphorescent materials provides higher current efficiency (cd/A) than one comprising fluorescent materials, when the conventional materials such as BAlq or CBP are used as phosphorescent host materials, a significantly high driving voltage is necessary compared to an organic EL device using a fluorescent material. Thus, there is no merit in terms of power efficiency (lm/W). (3) Further, the operation lifetime of an organic EL device is short and luminous efficiency is still required to be improved.
  • International Patent Publication No. WO 2006/049013 discloses compounds for organic electroluminescent materials having a condensed bicyclic group as a backbone structure. However, it does not disclose a compound having a nitrogen-containing condensed bicyclic group, a carbazole group which is substituted with an aromatic ring-fused cycloalkyl or heterocycloalkyl group at each of the 3- and 9- positions, and an aromatic ring-fused heterocycloalkyl or cycloalkyl group.
    •
  • The objective of the present invention is to provide a compound for organic electronic material, which has an excellent structure imparting high luminous efficiency and a long operation lifetime to a device, and having proper color coordination; and an organic electroluminescent device, which has high efficiency and a long lifetime, using said compounds.
  • The present inventors found that the above objective can be achieved by a compound represented by the following formula 1:
  • ---------- (1)
  • wherein
  • L₁ and L₂ each independently represent a single bond, a substituted or unsubstituted 5- to 30-membered heteroarylene group, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (C6-C30)cycloalkylene group;
  • X₁ represents CH or N;
  • Y₁ and Y₂ each independently represent -O-, -S-, -CR8R9- or -NR₁0-;
  • R₁ to R10 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted 5- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group fused with at least one (C3-C30)cycloalkyl group, a 5- to 7-membered heterocycloalkyl group fused with at least one substituted or unsubstituted (C6-C30)aromatic ring, a (C3-C30)cycloalkyl group fused with at least one substituted or unsubstituted (C6-C30)aromatic ring, -NR21R22, -SiR23R24R25, -SR26, -OR27, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C2-C30)alkynyl group, a cyano group, a nitro group, or a hydroxyl group; or are linked to an adjacent substituent via a substituted or unsubstituted (C3-C30)alkylene or a (C3-C30)alkenylene group to form a mono- or polycyclic, alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;
  • R21 to R27 have the same definition as one of R₁ to R10;
  • a, b, e and g each independently represent an integer of 1 to 4; where a, b, e or g is an integer of 2 or more, each of R₁, each of R2, each of R5 or each of R7 is the same or different;
  • c, d and f each independently represent an integer of 1 to 3; where c, d or f is an integer of 2 or more, each of R3, each of R4, or each of R6 is the same or different; and
  • the heterocycloalkyl group and the heteroaryl(ene) group contain at least one hetero atom selected from B, N, O, S, P(=O), Si and P.
    •
  • The compounds for organic electronic material according to the present invention can manufacture an organic electroluminescent device which has high luminous efficiency and a long operation lifetime.
  • Hereinafter, the present invention will be described in detail. However, the following description is intended to explain the invention, and is not meant in any way to restrict the scope of the invention.
  • The present invention relates to a compound for organic electronic material represented by the above formula 1 and an organic electroluminescent device comprising the compound.
  • Herein, “(C1-C30)alkyl(ene)” is meant to be a linear or branched alkyl(ene) having 1 to 30 carbon atoms, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc.; “(C2-C30) alkenyl(ene)” is meant to be a linear or branched alkenyl(ene) having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.; “(C2-C30)alkynyl” is a linear or branched alkynyl having 2 to 30 carbon atoms, in which the number of carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl, etc.; “(C1-C30)alkoxy” is a linear or branched alkoxy having 1 to 30 carbon atoms, in which the number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and includes methoxy, ethoxy, propoxy, isopropoxy, 1-ethylpropoxy, etc.; “(C3-C30)cycloalkyl” is a mono- or polycyclic hydrocarbon having 3 to 30 carbon atoms, in which the number of carbon atoms is preferably 3 to 20, more preferably 3 to 7, and includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc.; “(C6-C30)cycloalkylene” is one formed by removing a hydrogen from cycloalkyl having 6 to 30, preferably 6 to 20, more preferably 6 or 7 carbon atoms; and “5- to 7-membered heterocycloalkyl” is a cycloalkyl having at least one heteroatom selected from B, N, O, S, P(=O), Si and P, preferably N, O and S, and 5 to 7 ring backbone atoms, and includes tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc.; “(C6-C30)aryl(ene)” is a monocyclic or fused ring derived from an aromatic hydrocarbon having 6 to 30 carbon atoms, in which the number of carbon atoms is preferably 6 to 20, more preferably 6 to 12, and includes phenyl, biphenyl, terphenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, etc. Further, “3- to 30-membered heteroaryl(ene)” is an aryl having at least one, preferably 1 to 4 heteroatom selected from the group consisting of B, N, O, S, P(=O), Si and P, and 3 to 30 ring backbone atoms; is a monocyclic ring or fused ring condensed with at least one benzene ring; has preferably 5 to 21, more preferably 5 to 12 ring backbone atoms; may be partially saturated; may be one formed by linking at least one heteroaryl or aryl group to a heteroaryl group via a single bond(s); and includes a monocyclic ring-type heteroaryl including furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc., and a fused ring-type heteroaryl including benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzoimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl, etc. “Halogen” includes F, Cl, Br and I.
  • Herein, “substituted” in the expression “substituted or unsubstituted” means that a hydrogen atom in a certain functional group is replaced with another atom or group, i.e., a substituent. Substituents of the substituted alkyl(ene) group, the substituted alkenyl group, the substituted alkynyl group, the substituted cycloalkylene group, the substituted cycloalkyl group, the substituted heterocycloalkyl group, the substituted aryl(ene) group, the substituted heteroaryl(ene) group and the substituted aromatic ring in said L₁ and L₂, R₁ to R10 and R21 to R27 groups are each independently at least one selected from the group consisting of deuterium, a halogen, a (C1-C30)alkyl substituted or unsubstituted with a halogen, a (C6-C30)aryl, a 5- to 30-membered heteroaryl substituted or unsubstituted with a (C6-C30)aryl, a (C3-C30)cycloalkyl group, a 5- to 7-membered heterocycloalkyl group, a (C1-C30)alkyl silyl group, a (C6-C30)aryl silyl group, a (C1-C30)alkyl (C6-C30)aryl silyl group, a (C2-C30)alkenyl group, a (C2-C30)alkynyl group, a cyano group, a carbazolyl group, a (C1-C30)alkyl amino group, a (C6-C30)aryl amino group, a (C1-C30)alkyl (C6-C30)aryl amino group, a (C6-C30)aryl boronyl group, a (C1-C30)alkyl boronyl, a (C1-C30)alkyl (C6-C30)aryl boronyl, a (C6-C30)aryl (C1-C30)alkyl group, a (C1-C30)alkyl (C6-C30)aryl group, a carbonyl group, a carboxyl group, a nitro group and a hydroxyl group.
  • In the above formula 1, L₁ and L₂ each independently are preferably a single bond, a substituted or unsubstituted 5- to 21-membered heteroarylene group, a substituted or unsubstituted (C6-C20)arylene group, or a substituted or unsubstituted (C6-C20)cycloarylene group, more preferably one selected from group consisting of a single bond, phenylene, naphthylene, biphenylene, terphenylene, anthrylene, andenylene, fluorenylene, phenanthrylene, triphenylenylene, pyrenylene, phenylenylene, chrysenylene, naphthasenylene, fluorantenyl, furylene, thiophenylene, pyrrolylene, imidazolylene, pyrazolylene, thiazolylene, thiadiazolylene, isothiazolylene, isoxazolylene, oxazolylene, oxadiazolylene, triazinylene, tetrazinylene, triazolylene, tetrazolylene, furazanylene, pyridylene, pyrazinylene, pyrimidinylene, pyridazinylene, benzofuranylene, benzothiophenylene, isobenzofuranylene, benzoimidazolylene, benzothiazolylene, benzoisothiazolylene, benzoisoxazolylene, benzooxazolylene, isoindolylene, indolylene, indazolylene, benzothiadiazolylene, quinolylene, isoquinolylene, cinnolinylene, quinazolinylene, quinoxalinylene, carbazolylene, phenanthridinylene, benzodioxolylene, dibenzofuranylene and dibenzothiophenylene.
  • In the above formula 1, Y₁ and Y₂ each independently represent -O-, -S-, -CR8R9- or -NR10-, wherein R8 and R9 preferably each independently a substituted or unsubstituted (C1-C30)alkyl group or a substituted or unsubstituted (C6-C30)aryl group, or are linked to an adjacent substituent via a substituted or unsubstituted (C3-C30)alkylene or a (C3-C30)alkenylene group to form a mono- or polycyclic, alicyclic or aromatic ring, more preferably each independently represent an unsubstituted (C1-C10)alkyl group or an unsubstituted (C6-C12)aryl group, or are linked to an adjacent substituent to form a mono- or polycyclic, (C1-C10)alicyclic or (C6-C15)aromatic ring. And, R10 preferably represents a substituted or unsubstituted (C6-C30)aryl group or a substituted or unsubstituted 3- to 30-membered heteroaryl group, more preferably represents a (C6-C20)aryl group unsubstituted or substituted with deuterium, a halogen, a (C1-C6)alkyl or a (C6-C12)aryl, or a 5- to 21-membered heteroaryl group substituted with a (C6-C12)aryl.
  • In the above formula 1, R₁ to R7 preferably each independently represent hydrogen, a substituted or unsubstituted (C6-C30)aryl group or -SiR23R24R25, or are linked to an adjacent substituent via a substituted or unsubstituted (C3-C30)alkylene or a (C3-C30)alkenylene group to form a mono- or polycyclic, alicyclic or aromatic ring, more preferably each independently represent hydrogen, an unsubstituted (C6-C12)aryl group or -SiR23R24R25, or are linked to an adjacent substituent to form a mono- or polycyclic (C6-C12)aromatic ring.
  • In the above formula 1, is selected from the followingstructures, but are not limited thereto:
  • The representative compounds of the present invention include the following compounds:
  • The compounds for organic electronic materials according to the present invention can be prepared according to the following reaction scheme.
  • [Reaction Scheme]
  • wherein R₁ to R7, Y₁ and Y₂, X₁, L₁ and L₂, a, b, c, d, e, f and g are as defined in formula 1 above, and X represents a halogen.
  • In addition, the present invention provides an organic electroluminescent device comprising the compound of formula 1. Said organic electroluminescent device comprises a first electrode, a second electrode, and at least one organic layer between said first and second electrodes. Said organic layer comprises at least one compound of formula 1 according to the present invention. Further, said organic layer comprises a light-emitting layer in which the compound of formula 1 is comprised as a host material.
  • In addition, a phosphorescent dopant, which is used for an organic electroluminescent device together with the host material according to the present invention, may be selected from compounds represented by the following formula 2:
  • --------------------- (2)
  • wherein M₁ is selected from the group consisting of Ir, Pt, Pd and Os; L101, L102 and L103 are each independently selected from the following structures:
  • R201 to R203 each independently represent hydrogen, deuterium, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), a (C6-C30)aryl group unsubstituted or substituted with (C1-C30)alkyl group(s), or a halogen;
  • R204 to R219 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C1-C30)alkoxy group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted mono- or di-(C1-C30)alkylamino group, a substituted or unsubstituted mono- or di-(C6-C30)arylamino group, SF5, a substituted or unsubstituted tri(C1-C30)alkylsilyl group, a substituted or unsubstituted di(C1-C30)alkyl(C6-C30)arylsilyl group, a substituted or unsubstituted tri(C6-C30)arylsilyl group, a cyano group or a halogen;
  • R220 to R223 each independently represent hydrogen, deuterium, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), or a (C6-C30)aryl group unsubstituted or substituted with (C1-C30)alkyl group(s);
  • R224 and R225 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, or a halogen, or R224 and R225 may be linked to each other via a (C3-C12)alkylene group or (C3-C12)alkenylene group with or without a fused ring, to form a mono- or polycyclic, alicyclic or aromatic ring;
  • R226 represents a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 5- or 30-membered heteroaryl group or a halogen;
  • R227 to R229 each independently represent hydrogen, deuterium, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group or a halogen;
  • Q represents or ;R231 to R242 each independently represent hydrogen, deuterium, a (C1-C30)alkyl group unsubstituted or substituted with halogen(s), a (C1-C30)alkoxy group, a halogen, a substituted or unsubstituted (C6-C30)aryl group, a cyano group, or a substituted or unsubstituted (C5-C30)cycloalkyl group, or each of R231 to R242 may be linked to an adjacent substituent via (C2-C30)alkylene group or (C2-C30)alkenylene group to form a spiro ring or a fused ring or may be linked to R207 or R208 via a (C2-C30)alkylene group or (C2-C30)alkenylene group to form a saturated or unsaturated fused ring.
  • The dopants of formula 2 include the following, but are not limited thereto:
  • The organic electroluminescent device according to the present invention may further comprise, in addition to the compounds represented by formula 1, at least one compound selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.
  • In the organic electroluminescent device according to the present invention, the organic layer may further comprise at least one metal selected from the group consisting of metals of Group 1, metals of Group 2, transition metals of the 4th period, transition metals of the 5th period, lanthanides and organic metals of d-transition elements of the Periodic Table, or at least one complex compound comprising said metal. The organic layer may comprise a light-emitting layer and a charge generating layer.
  • The organic electroluminescent device according to the present invention may emit a white light by further comprising at least one light-emitting layer which comprises a blue electroluminescent compound, a red electroluminescent compound or a green electroluminescent compound, in addition to said organic layer comprising the compound according to the present invention.
  • Preferably, in the organic electroluminescent device according to the present invention, at least one layer (hereinafter, "a surface layer”) selected from a chalcogenide layer, a metal halide layer and a metal oxide layer may be placed on an inner surface(s) of one or both electrode(s). Specifically, it is preferred that a chalcogenide(includes oxides) layer of silicon or aluminum is placed on an anode surface of an electroluminescent medium layer, and a metal halide layer or metal oxide layer is placed on a cathode surface of an electroluminescent medium layer. Such a surface layer provides operation stability for the organic electroluminescent device. Preferably, said chalcogenide includes SiOX(1≤X≤2), AlOX(1≤X≤1.5), SiON, SiAlON, etc.; said metal halide includes LiF, MgF2, CaF2, a rare earth metal fluoride, etc.; and said metal oxide includes Cs2O, Li2O, MgO, SrO, BaO, CaO, etc.
  • Preferably, in the organic electroluminescent device according to the present invention, a mixed region of an electron transport compound and an reductive dopant, or a mixed region of a hole transport compound and an oxidative dopant may be placed on at least one surface of a pair of electrodes. In this case, the electron transport compound is reduced to an anion, and thus it becomes easier to inject and transpor electrons from the mixed region to an electroluminescent medium. Further, the hole transport compound is oxidized to a cation, and thus it becomes easier to inject and transport holes from the mixed region to the electroluminescent medium. Preferably, the oxidative dopant includes various Lewis acids and acceptor compounds; and the reductive dopant includes alkali metals, alkali metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof. A reductive dopant layer may be employed as a charge generating layer to prepare an electroluminescent device having two or more electroluminescent layers and emitting a white light.
  • Hereinafter, the compound for organic electronic material, the preparation method of the compound, and the luminescent properties of the device comprising the compound of the present invention will be explained in detail with reference to the following examples:
  • Preparation Example 1: Preparation of compound C-2
  • Preparation of compound C-1-1
  • 9-phenyl-9H-carbazol-3-yl boronic acid (14 g, 48.76 mmol), 3-bromo-9H-carbazole (10 g, 40.63 mmol), K2CO3 (13.5 g, 97.52 mmol) and Pd(PPh3)4 (2.35 g, 2.03 mmol) were added to a mixture of toluene 200mL, EtOH 50mL and purified water 50mL. After stirring the reaction mixture for 3 hours at 90~100°C, the mixture was cooled to room temperature. An aqueous layer was removed from the mixture by a gravity separation. The obtained organic layer was concentrated, was triturated with methylene chloride (MC), and then was filtered to produce compound C-1-1 (12 g, 72%).
  • Preparation of compound C-1-2
  • After dissolving 2,4-dichloroquinazoline (30g, 151mmol), 9-phenyl-9H-carbazol-3-yl boronic acid (15.6g, 75.3mmol), Pd(PPh3)4 (2.6g, 2.3mmol) and Na2CO3 (16g, 150mmol) in a mixture of toluene (300mL) and distilled water (75mL), the reaction mixture was stirred for 2 hours at 90°C. The resulting organic layer was distillated under reduced pressure, and then was triturated with MeOH. The obtained solid was dissolved in MC, was filtered through silica, and then was triturated with MC and hexane to produce compound C-1-2 (9.3g, 51.4%).
  • Preparation of compound C-2
  • After suspending compound C-1-1 (5.3 g, 14.7 mmol) and compound C-1-2 (6.4 g, 15.8 mmol) in dimethyl formamide (DMF) 80mL, 60% NaH (948 mg, 22 mmol) was added to the mixture at room temperature. The obtained reaction mixture was stirred for 12 hours. After adding purified water (1L), the mixture was filtered under reduced pressure. The obtained solid was triturated with MeOH/ethyl acetate, was dissolved in MC, was filtered through silica, and then was triturated with MC/n-hexane to obtain compound C-2 (1.9 g, 16.8%).
  • MS/FAB found 778; calculated 777.91
  • Preparation Example 2: Preparation of compound C-13
  • Preparation of compound C-2-1
  • After dissolving 2,4-dichloroquinazoline (50 g, 251 mmol) and dibenzo[b,d]furan-4-yl boronic acid (53.2g, 251 mmol) in a mixture of toluene (1 L) and water (200 mL), tetrakistriphenylphosphine palladium (14.5 g, 12.5 mmol) and sodium carbonate (80 g, 755 mmol) were added to the reaction mixture. The reaction mixture was stirred for 20 hours at 80°C, and cooled to room temperature. After terminating the reaction with ammonium chloride aqueous solution 200 mL, the reaction mixture was extracted with ethyl acetate 1 L, and further an aqueous layer was extracted with dichloromethane 1 L. An organic layer was dried with anhydrous magnesium sulfate, and removed under reduced pressure. The obtained solid was filtered through silica gel, and the solution was removed under reduced pressure. The obtained solid was washed with ethyl acetate (EtOAc) 100 mL to produce compound C-2-1 (50 g, 74 %).
  • Preparation of compound C-13
  • After dissolving compound C-1-1 (50 g, 122 mmol) in DMF, 60 % NaH (5.9 g, 148 mmol) was added slowly to the reaction mixture. After stirring the reaction mixture for 1 hour at room temperature, compound C-2-1 (51 g, 147 mmol) was added to the reaction mixture. The reaction mixture was stirred for 20 hours at room temperature. Ice water was dropped slowly to the reaction mixture to terminate the reaction. And then, the reaction mixture was filtered to obtain the produced solid. The obtained solid was washed with water 1 L, and subsequently with MeOH 1 L. The obtained solid was dried, dissolved in CHCl3 4 L, and filtered through silica gel to remove an inorganic material. The solvent in the obtained solution was removed to obtain solid. The obtained solid was recrystallized in DMF to obtain compound C-13 (50 g, 58 %).
  • MS/FAB found 703; calculated 702.80
  • Preparation Example 3: Preparation of compound C-14
  • Preparation of compound C-3-1
  • After dissolving 2,4-dichloroquinazoline (50 g, 251 mmol) and dibenzo[b,d]thiophen-4-yl boronic acid (57.3g, 251 mmol) in a mixture of toluene (1 L) and water (200 mL), tetrakistriphenylphosphine palladium (14.5 g, 12.5 mmol) and sodium carbonate (80 g, 755 mmol) were added to the reaction mixture. The reaction mixture was stirred for 20 hours at 80°C, and cooled to room temperature. After terminating the reaction with ammonium chloride aqueous solution 200 mL, the reaction mixture was extracted with ethyl acetate 1 L, and further an aqueous layer was extracted with dichloromethane 1 L. An organic layer was dried with anhydrous magnesium sulfate, and removed under reduced pressure. The obtained solid was filtered through silica gel, and the solution was removed under reduced pressure. The obtained solid was washed with ethyl acetate (EtOAc) 100 mL to produce compound C-3-1 (50 g, 60 %).
  • Preparation of compound C-14
  • After dissolving compound C-1-1 (50 g, 122 mmol) in DMF, 60 % NaH (5.9 g, 148 mmol) was added slowly to the reaction mixture. After stirring the reaction mixture for 1 hour at room temperature, compound C-3-1 (51 g, 147 mmol) was added to the reaction mixture. The reaction mixture was stirred for 20 hours at room temperature. Ice water was dropped slowly to the reaction mixture to terminate the reaction. And then, the reaction mixture was filtered to obtain the produced solid. The obtained solid was washed with water 1 L, and subsequently with MeOH 1 L. The obtained solid was dried, dissolved in CHCl3 4 L, and filtered through silica gel to remove an inorganic material. The solvent in the obtained solution was removed to obtain solid. The obtained solid was recrystallized in DMF to obtain compound C-14 (50 g, 57 %).
  • MS/FAB found 729; calculated 718.87
  • Preparation Example 4: Preparation of compound C-20
  • Preparation of compound C-4-1
  • After dissolving dibenzo[b,d]furan-4-yl boronic acid (19 g, 89.6 mmol), bromobenzene (18.4 ml, 138 mmol), Pd(PPh3)4 (2.9 g, 2.5 mmol) and Na2CO3 (23.2 g, 219 mmol) in a mixture of toluene (375mL), EtOH (75mL) and distilled water (75mL), the reaction mixture was stirred for 4 hours at 90°C. The resulting organic layer was distillated under reduced pressure, and then was filtered through column with MC and hexane to obtain compound C-4-1 (17 g, 77 %).
  • Preparation of compound C-4-2
  • After dissolving compound C-4-1 (17 g, 65.3 mmol) in tetrahydrofuran (THF) (500 ml), and adding 2.5 M n-BuLi in hexane (52.2 ml, 130 mmol) to the reaction mixture in -78°C, the reaction mixture was stirred for 1 hour. The reaction mixture was stirred for 2 hours with adding B(Oi-Pr)₃ (21.8 ml, 195 mmol) slowly to the reaction mixture. After quenching the reaction mixture with adding 2 M HCl, the reaction mixture was extracted with distilled water and EA. The obtained solid was recrystallized with MC and hexane to obtain compound C-4-2 (6.4 g, 33%).
  • Preparation of compound C-4-3
  • After dissolving compound C-4-2 (4.9 g, 24.4 mmol), 2,4-dichloroquinazoline (6.4 g, 22.2 mmol), Pd(PPh3)4 (1.1 g, 2.5 mmol) and Na2CO3 (7.1 g, 66.6 mmol) in a mixture of toluene (300mL) and distilled water (75mL), the reaction mixture was stirred for 2 hours at 90°C. The resulting organic layer was distillated under reduced pressure, and then was triturated with MeOH. The obtained solid was dissolved in MC and filtered through silica gel, and then was triturated with MC and hexane to obtain compound C-4-3 (4.1 g, 45%).
  • Preparation of compound C-20
  • After suspending compound C-4-3 (4.5 g, 10.9 mmol) and compound C-1-1 (4.1 g, 9.9 mmol) in DMF 80mL, 60% NaH (594 mg, 14.8 mmol) was added to the mixture at room temperature. The obtained reaction mixture was stirred for 12 hours. After adding purified water (1L), the mixture was filtered under reduced pressure. The obtained solid was triturated with MeOH/ethyl acetate, and with DMF, and then with EA/THF. The obtained solid was dissolved in MC, was filtered through silica, and then was triturated with MeOH/EA to obtain compound C-20 (3.4 g, 44 %).
  • MS/FAB found 779; calculated 778.90
  • Preparation Example 5: Preparation of compound C-21
  • Preparation of compound C-5-1
  • After dissolving dibenzo[b,d]thiophen-4-yl boronic acid (20 g, 87.7 mmol), bromobenzene (18.4 ml, 175 mmol), Pd(PPh3)4 (2.9 g, 2.5 mmol) and Na2CO3 (23.2 g, 219 mmol) in a mixture of toluene (375mL), EtOH (75mL) and distilled water (75mL), the reaction mixture was stirred for 4 hours at 90°C. The resulting organic layer was distillated under reduced pressure, and then was filtered through column with MC and hexane to obtain compound C-5-1 (17 g, 75 %).
  • Preparation of compound C-5-2
  • After dissolving compound C-5-1 (17 g, 65.3 mmol) in (THF (500 ml), and adding 2.5 M n-BuLi in hexane (52.2 ml, 130 mmol) to the reaction mixture in -78°C, the reaction mixture was stirred for 1 hour. The reaction mixture was stirred for 2 hours with adding B(Oi-Pr)₃ (21.8 ml, 195 mmol) slowly to the reaction mixture. After quenching the reaction mixture with adding 2 M HCl, the reaction mixture was extracted with distilled water and EA. The obtained solid was recrystallized with MC and hexane to obtain compound C-5-2 (11.5 g, 60%).
  • Preparation of compound C-5-3
  • After dissolving compound C-5-2 (8.3 g, 41.5 mmol), 2,4-dichloroquinazoline (11.5 g, 37.8 mmol), Pd(PPh3)4 (2.2 g, 2.5 mmol) and Na2CO3 (12 g, 113 mmol) in a mixture of toluene (300mL) and distilled water (75mL), the reaction mixture was stirred for 2 hours at 90°C. The resulting organic layer was distillated under reduced pressure, and then was triturated with MeOH. The obtained solid was dissolved in MC and filtered through silica gel, and then was triturated with MC and hexane to obtain compound C-5-3 (10 g, 68%).
  • Preparation of compound C-21
  • After suspending compound C-5-3 (5 g, 11.8 mmol) and compound C-1-1 (4.8 g, 11.8 mmol) in DMF 80mL, 60% NaH (881 mg, 22 mmol) was added to the mixture at room temperature. The obtained reaction mixture was stirred for 12 hours. After adding purified water (1L), the mixture was filtered under reduced pressure. The obtained solid was triturated with MeOH/ethyl acetate, and with DMF, and then with EA/THF. The obtained solid was dissolved in MC, was filtered through silica, and then was triturated with MeOH/EA to obtain compound C-21 (4.8 g, 51 %).
  • MS/FAB found 795; calculated 794.96
  • Preparation Example 6: Preparation of compound C-33
  • Preparation of compound C-6-1
  • After dissolving dibenzo[b,d]furan-4-yl boronic acid (20 g, 94.34 mmol), 1-bromo-4-iodo-benzene (53.4 ml, 188.68 mmol), Pd(PPh3)4 (5.45 g, 4.72 mmol) and K2CO3 (39.1 g, 283.01 mmol) in a mixture of toluene (900mL), EtOH (200mL) and distilled water (200mL), the reaction mixture was stirred for 3 hours at 70~80°C. After terminating the reaction, an aqueous layer was removed from the mixture by a gravity separation. And then, the obtained organic layer was concentrated and purified through column to obtain compound C-6-1 (17 g, 56 %).
  • Preparation of compound C-6-2
  • After dissolving compound C-6-1 (17 g, 52.6 mmol) in THF (400 ml), and adding 2.5 M n-BuLi in hexane (31.5 ml, 78.9 mmol) to the reaction mixture in -78°C, the reaction mixture was stirred for 1 hour. The reaction mixture was stirred for 12 hours with adding B(Oi-Pr)₃ (24.1 ml, 105.2 mmol) slowly to the reaction mixture. After terminating the reaction, purified water 20 mL was dropped slowly to the reaction mixture. The reaction mixture was extracted with EA/NH4Cl aqueous solution. The obtained organic layer was concentrated, was triturated with MC/hexane, and then was filtered to obtain compound C-6-2 (14.5 g, 96 %).
  • Preparation of compound C-6-3
  • After dissolving compound C-6-2 (4.5 g, 50.33 mmol), 2,4-dichloroquinazoline (11.5 g, 50.33 mmol), Na2CO3 (20.9 g, 150.99 mmol) and Pd(PPh3)4 (2.9 g, 2.52 mmol) in a mixture of toluene (300mL), EtOH (75mL) and distilled water (75mL), the reaction mixture was stirred for 12 hours at 75~80°C. After terminating the reaction, the reaction mixture was cooled to room temperature, and an aqueous layer was removed from the mixture by a gravity separation. The obtained organic layer was concentrated, was triturated with THF/MeOH, was filtered, and then was dried. The dried compound was dissolved in chloroform 3 L, and filtered through silica. The remaining solution was concentrated and triturated with EA to obtain compound C-6-3 (3.8 g, 19 %).
  • Preparation of compound C-33
  • After suspending compound C-1-1 (3.8 g, 9.34 mmol) and compound C-6-3 (3.8 g, 9.34 mmol) in DMF 80mL, 60% NaH (1.12 g, 28.02 mL) was added to the mixture at room temperature. The obtained reaction mixture was stirred for 12 hours. After adding purified water (1L), the mixture was filtered under reduced pressure. The obtained solid was triturated with MeOH/ethyl acetate, and with DMF, and then with EA/THF. The obtained solid was dissolved in MC, was filtered through silica, and then was triturated with MeOH/EA to obtain compound C-33 (2.9 g, 40 %).
  • MS/FAB found 779; calculated 778.90
  • Preparation Example 7: Preparation of compound C-34
  • Preparation of compound C-7-1
  • After dissolving 1-bromo-4-iodo-benzene (49.6 g, 0.17 mol), dibenzo[b,d]thiophen-4-yl boronic acid (20 g, 0.087 mol), Pd(PPh3)4 (5.0 g, 0.044 mol) and Na2CO3 (18.5 g, 0.18 mol) in a mixture of toluene (880mL) and H2O (200mL) in 2000 mL round-bottom flask, the reaction mixture was stirred for 12 hours at 80°C. After terminating the reaction, the reaction mixture was extracted with ethyl acetate. And then, the obtained organic layer was dried with MgSO4 and filtered. After removing a solvent from the organic layer under reduced pressure, the organic layer was filtered through adsorption column to obtain white solid, compound C-7-1 (21.2 g, 71 %).
  • Preparation of compound C-7-2
  • After putting compound C-7-1 (21.4 g, 0.06 mol) and dry THF (1000 ml) in 2000 mL round-bottom flask under anhydrous conditions, n-BuLi in hexane (37 ml, 2.25 M solution) was added slowly to the reaction mixture at -78°C with stirring the mixture under nitrogen. The reaction mixture was stirred for 1 hour at -78°C. After adding B(Oi-Pr)₃ (29 ml, 0.13 mol) slowly to the reaction mixture at -78°C, the reaction mixture was heated to room temperature and reacted for 12 hours. After terminating the reaction, the reaction mixture was extracted with ethyl acetate. And then, the obtained organic layer was dried with MgSO4 and filtered. After removing a solvent from the organic layer under reduced pressure, the organic layer was filtered through column to obtain white solid, compound C-7-2 (15.5 g, 81 %).
  • Preparation of compound C-7-3
  • After adding compound C-7-2 (15.5 g, 0.051 mol), 2,4-dichloroquinazoline (12.2 g, 0.06 mol), Na2CO3 (16.2 g, 0.153 mol) and Pd(PPh3)4 (2.94 g, 0.0025 mol) in a mixture of toluene (250mL), EtOH (40mL) and H2O (70mL) in 250 mL round-bottom flask, the reaction mixture was stirred for 12 hours at 80°C. After terminating the reaction, the reaction mixture was extracted with ethyl acetate. And then, the obtained organic layer was dried with MgSO4 and filtered. After removing a solvent from the organic layer under reduced pressure, the obtained solid was recrystallized to obtain compound C-7-3 (14 g, 65 %).
  • Preparation of compound C-34
  • NaH 60 % (0.62 g, 0.0154 mol) and DMF (60 ml) was put in 250 mL round-bottom flask under anhydrous conditions. After dissolving compound C-1-1 (4.83 g, 0.012 mol) in DMF (30 ml), the mixture was put in the round-bottom flask. The reaction mixture was stirred for 1 hour. After dissolving compound C-7-3 (5 g, 0.012 mol) in DMF (30 ml), the mixture was put in the round-bottom flask. After stirring the mixture for 12 hours, yellow solid was filtered, was washed with MeOH, was triturated with THF, and then was triturated with DMF to obtain compound C-34 (4.2 g, 45 %).
  • MS/FAB found 795; calculated 794.96
  • Preparation Example 8: Preparation of compound C-36
  • Preparation of compound C-8-1
  • After dissolving dibenzo[b,d]furan-4-yl boronic acid (20 g, 94.34 mmol), 1,3-dibromobenzene (22.3 g, 94.34 mmol), Pd(PPh3)4 (5.45 g, 4.72 mmol) and K2CO3 (39.1 g, 283.01 mmol) in a mixture of toluene (800mL), EtOH (200mL) and distilled water (200mL), the reaction mixture was stirred for 3 hours at 70~80°C. After terminating the reaction, an aqueous layer was removed from the mixture by a gravity separation. And then, the obtained organic layer was concentrated and purified through silica column to obtain compound C-8-1 (13 g, 43 %).
  • Preparation of compound C-8-2
  • After dissolving compound C-8-1 (13 g, 40.23 mmol) in THF (300 ml), and adding 2.5 M n-BuLi in hexane (19 ml, 48.27 mmol) to the reaction mixture in -78°C, the reaction mixture was stirred for 1 hour. The reaction mixture was stirred for 12 hours with adding B(Oi-Pr)₃ (13.9 ml, 60.34 mmol) slowly to the reaction mixture. After terminating the reaction, purified water 20 mL was dropped slowly to the reaction mixture. The reaction mixture was extracted with EA/NH4Cl aqueous solution. The obtained organic layer was concentrated, was triturated with MC/hexane, and then was filtered to obtain compound C-8-2 (6.8 g, 58.7 %).
  • Preparation of compound C-8-3
  • After dissolving compound C-8-2 (6.8 g, 23.6 mmol), 2,4-dichloroquinazoline (5.38 g, 23.6 mmol), Na2CO3 (9.8 g, 70.8 mmol) and Pd(PPh3)4 (1.36 g, 1.18 mmol) in a mixture of toluene (240mL) and distilled water (50mL), the reaction mixture was stirred for 12 hours at 90~100°C. After terminating the reaction, the reaction mixture was cooled to room temperature, and an aqueous layer was removed from the mixture by a gravity separation. The obtained organic layer was concentrated, was triturated with THF/MeOH, was filtered, and then was dried. The dried compound was dissolved in chloroform 3 L, and filtered through silica. The remaining solution was concentrated and triturated with THF/MeOH to obtain compound C-8-3 (3.8 g, 40 %).
  • Preparation of compound C-36
  • After suspending compound C-1-1 (3.8 g, 9.34 mmol) and compound C-8-3 (3.8 g, 9.34 mmol) in DMF 80mL, 60% NaH (1.12 g, 28.02 mL) was added to the mixture at room temperature. The obtained reaction mixture was stirred for 12 hours. After adding purified water (1L), the mixture was filtered under reduced pressure. The obtained solid was triturated with MeOH/ethyl acetate, was dissolved in MC, was filtered through silica, and then was triturated with MC/n-hexane to obtain compound C-36 (1.6 g, 21 %).
  • MS/FAB found 779; calculated 778.90
  • Preparation Example 9: Preparation of compound C-37
  • Preparation of compound C-9-1
  • After dissolving 1,3-dibromobenzene (16.5 g, 0.2 mol), dibenzo[b,d]thiophen-4-yl boronic acid (15 g, 0.06 mol), Pd(PPh3)4 (3.8 g, 0.003 mol) and Na2CO3 (14 g, 0.13 mol) in a mixture of toluene (330mL) and H2O (70mL) in 2000 mL round-bottom flask, the reaction mixture was stirred for 12 hours at 80°C. After terminating the reaction, the reaction mixture was extracted with ethyl acetate. And then, the obtained organic layer was dried with MgSO4 and filtered. After removing a solvent from the organic layer under reduced pressure, the organic layer was filtered through column to obtain white solid, compound C-9-1 (8.4 g, 40 %).
  • Preparation of compound C-9-2
  • After putting compound C-9-1 (8.4 g, 0.025 mol) and dry THF (200 ml) in 500 mL round-bottom flask under anhydrous conditions, n-BuLi in hexane (15 ml, 2.25 M solution) was added slowly to the reaction mixture at -78°C with stirring the mixture under nitrogen. The reaction mixture was stirred for 1 hour at -78°C. After adding B(Oi-Pr)₃ (11.4 ml, 0.05 mol) slowly to the reaction mixture at -78°C, the reaction mixture was heated to room temperature and reacted for 12 hours. After terminating the reaction, the reaction mixture was extracted with ethyl acetate. And then, the obtained organic layer was dried with MgSO₄and filtered. After removing a solvent from the organic layer under reduced pressure, the organic layer was filtered through column to obtain white solid, compound C-9-2 (6 g, 80 %).
  • Preparation of compound C-9-3
  • After adding compound C-9-2 (5.9 g, 0.02 mol), 2,4-dichloroquinazoline (4.6 g, 0.02 mol), Na2CO3 (6.2 g, 0.058 mol) and Pd(PPh3)4 (1.1 g, 0.00097 mol) in a mixture of toluene (100mL), EtOH (14mL) and H2O (30mL) in 250 mL round-bottom flask, the reaction mixture was stirred for 3 hours at 70°C. After terminating the reaction, the reaction mixture was extracted with ethyl acetate. And then, the obtained organic layer was dried with MgSO₄and filtered. After removing a solvent from the organic layer under reduced pressure, the organic layer was filtered through column to obtain compound C-9-3 (7.0 g, 85 %).
  • Preparation of compound C-37
  • NaH 60 % (0.5 g, 0.013 mol) and DMF (40 ml) was put in 250 mL round-bottom flask under anhydrous conditions. After dissolving compound C-1-1 (3.7 g, 0.009 mol) in DMF (30 ml), the mixture was put in the round-bottom flask. The reaction mixture was stirred for 1 hour. After dissolving compound C-9-3 (4 g, 0.0095 mol) in DMF (30 ml), the mixture was put in the round-bottom flask. After stirring the mixture for 12 hours, yellow solid was filtered, was washed with MeOH, was triturated with THF, and then was triturated with DMF to obtain compound C-37 (1.7 g, 20 %).
  • MS/FAB found 795; calculated 794.96
  • Preparation Example 10: Preparation of compound C-39
  • Preparation of compound C-10-1
  • After putting compound C-1-1 (14 g, 34.3 mmol) and 1-bromo-4-iodobenzene (48.5 g, 171.4 mmol), CuI (3.3 g, 17.1 mmol), K3PO4 (21.8 g, 102.9 mmol) and ethylene diamine (EDA) (2.3 ml, 34.3 mmol) into toluene (500 ml), the reaction mixture was stirred under reflux for 1 day. The reaction mixture was extracted with EA, was distilled under reduced pressure, and then was filtered through column with MC/hexane to obtain compound C-10-1 (15.5 g, 80.1 %)
  • Preparation of compound C-10-2
  • After dissolving compound C-10-1 (15.5 g, 27.5 mmol) in THF (250 ml), and adding 2.5 M n-BuLi in hexane (17.6 ml, 44 mmol) to the reaction mixture in -78°C, the reaction mixture was stirred for 1 hour. The reaction mixture was stirred for 2 hours with adding B(Oi-Pr)₃ (12.6 ml, 55 mmol) slowly to the reaction mixture. After quenching the reaction mixture with adding 2 M HCl, the reaction mixture was extracted with distilled water and EA. The obtained solid was recrystallized with MC and hexane to obtain compound C-10-2 (8.7 g, 60 %).
  • Preparation of compound C-39
  • After dissolving compound C-3-1 (3.2 g, 9.2 mmol), compound C-10-2 (4.9 g, 9.2 mmol), Pd(PPh3)4 (532 mg, 0.46 mmol) and Na2CO3 (2.9 g, 27.6 mmol) in a mixture of toluene (55 ml), EtOH (14 ml) and distilled water (14 ml), the reaction mixture was stirred for 2 hours at 90°C. The reaction mixture was extracted with distilled water and EA, and then was filtered through column with MC and hexane to obtain compound C-39 (5.5 g, 75 %).
  • MS/FAB found 795; calculated 794.96
  • Preparation Example 11: Preparation of compound C-40
  • Preparation of compound C-40
  • After dissolving compound C-2-1 (3.2 g, 9.2 mmol), compound C-10-2 (4.9 g, 9.2 mmol), Pd(PPh3)4 (532 mg, 0.46 mmol) and Na2CO3 (2.9 g, 27.6 mmol) in a mixture of toluene (55 ml), EtOH (14 ml) and distilled water (14 ml), the reaction mixture was stirred for 2 hours at 90°C. The reaction mixture was extracted with distilled water and EA, and then was filtered through column with MC and hexane to obtain compound C-40 (5.5 g, 75 %).
  • MS/FAB found 779; calculated 778.90
  • Example 1: Production of an OLED device using the compound according to the present invention
  • OLED device was produced using the compound according to the present invention. A transparent electrode indium tin oxide (ITO) thin film (15 Ω/sq) on a glass substrate for an organic light-emitting diode (OLED) device (Samsung Corning, Republic of Korea) was subjected to an ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and then was stored in isopropanol. Then, the ITO substrate was mounted on a substrate holder of a vacuum vapor depositing apparatus. N1-(naphthalen-2-yl)-N4,N4-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N1-phenylbenzene-1,4-diamine was introduced into a cell of said vacuum vapor depositing apparatus, and then the pressure in the chamber of said apparatus was controlled to 10-6 torr. Thereafter, an electric current was applied to the cell to evaporate the above introduced material, thereby forming a hole injection layer having a thickness of 60nm on the ITO substrate. Then, N,N’-di(4-biphenyl)-N,N’-di(4-biphenyl)-4,4’-diaminobiphenyl was introduced into another cell of said vacuum vapor depositing apparatus, and was evaporated by applying electric current to the cell, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer. Thereafter, compound C-2 was introduced into one cell of the vacuum vapor depositing apparatus, as a host material, and compound D-11 was introduced into another cell as a dopant. The two materials were evaporated at different rates and were deposited in a doping amount of 4 to 20wt% to form a light-emitting layer having a thickness of 30 nm on the hole transport layer. Then, 9,10-di(1-naphthyl)-2-(4-phenyl-1-phenyl-1H-benzo[d]imidazole)anthracene was introduced into one cell and lithium quinolate was introduced into another cell. The two materials were evaporated at different rates and were deposited in a doping amount of 30 to 70wt% to form an electron transport layer having a thickness of 30nm on the light-emitting layer. Then, after depositing lithium quinolate as an electron injection layer having a thickness of 1 to 2nm on the electron transport layer, an Al cathode having a thickness of 150nm was deposited by another vacuum vapor deposition apparatus on the electron injection layer. Thus, an OLED device was produced. All the material used for producing the OLED device were those purified by vacuum sublimation at 10-6 torr.
  • The produced OLED device showed red emission having a luminance of 1,020cd/m2 and a current density of 14.0mA/cm2 at a driving voltage of 4.0V. Further, the minimum time taken to be reduced to 90% of the luminance at a luminance of 5,000nit was 60 hours.
  • Example 2 to 11: Production of an OLED device using the compound according to the present invention
  • An OLED device was produced in the same manner as one of Example 1, except for using those shown in the below Table as a host material and a dopant.
  • Comparative Example 1: Production of an OLED device using conventional electroluminescent compounds
  • An OLED device was produced in the same manner as that of Example 1, except that a light-emitting layer having a thickness of 30 nm was deposited on the hole transport layer by using 4,4’-N,N’-dicarbazol-biphenyl (CBP) as a host material and compound D-11 as a dopant and that a hole blocking layer having a thickness of 10 nm was deposited by using aluminum(III) bis(2-methyl-8-quinolinato)-4-phenylphenolate.
  • The produced OLED device showed red emission having a luminance of 1,000cd/m2 and a current density of 20.0mA/cm2 at a driving voltage of 8.2V. Further, the minimum time taken to be reduced to 90% of the luminance at a luminance of 5,000nit was 10 hours.
  • The results of examples and comparative example are shown in the following Table.
  • The compounds of the present invention have superior luminescent properties than the conventional materials. Further, the device using the compounds according to the present invention as a host material induces an increase in power efficiency by reducing a driving voltage, and thus can improve power consumption.
    •

Claims (6)

  1. A compound represented by the following formula 1:
    ---------- (1)
    wherein
    L₁ and L₂ each independently represent a single bond, a substituted or unsubstituted 5- to 30-membered heteroarylene group, a substituted or unsubstituted (C6-C30)arylene group, or a substituted or unsubstituted (C6-C30)cycloalkylene group;
    X₁ represents CH or N;
    Y₁ and Y₂ each independently represent -O-, -S-, -CR8R9- or -NR10-;
    R₁ to R10 each independently represent hydrogen, deuterium, a halogen, a substituted or unsubstituted (C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group, a substituted or unsubstituted 3- to 30-membered heteroaryl group, a substituted or unsubstituted (C3-C30)cycloalkyl group, a substituted or unsubstituted 5- to 7-membered heterocycloalkyl group, a substituted or unsubstituted (C6-C30)aryl(C1-C30)alkyl group, a substituted or unsubstituted (C6-C30)aryl group fused with at least one (C3-C30)cycloalkyl group, a 5- to 7-membered heterocycloalkyl group fused with at least one substituted or unsubstituted (C6-C30)aromatic ring, a (C3-C30)cycloalkyl group fused with at least one substituted or unsubstituted (C6-C30)aromatic ring, -NR21R22, -SiR23R24R25, -SR26, -OR27, a substituted or unsubstituted (C2-C30)alkenyl group, a substituted or unsubstituted (C2-C30)alkynyl group, a cyano group, a nitro group, or a hydroxyl group; or are linked to an adjacent substituent via a substituted or unsubstituted (C3-C30)alkylene or a (C3-C30)alkenylene group to form a mono- or polycyclic, alicyclic or aromatic ring whose carbon atom(s) may be replaced with at least one hetero atom selected from nitrogen, oxygen and sulfur;
    R21 to R27 have the same definition as one of R₁ to R10;
    a, b, e and g each independently represent an integer of 1 to 4; where a, b, e or g is an integer of 2 or more, each of R₁, each of R2, each of R5 or each of R7 is the same or different;
    c, d and f each independently represent an integer of 1 to 3; where c, d or f is an integer of 2 or more, each of R3, each of R4, or each of R6 is the same or different; and
    the heterocycloalkyl group and the heteroaryl(ene) group contain at least one hetero atom selected from B, N, O, S, P(=O), Si and P.
  2. The compound according to claim 1, characterized in that substituents of the substituted alkyl(ene) group, the substituted alkenyl group, the substituted alkynyl group, the substituted cycloalkylene group, the substituted cycloalkyl group, the substituted heterocycloalkyl group, the substituted aryl(ene) group, the substituted heteroaryl(ene) group and the substituted aromatic ring in said L₁ and L₂, R₁ to R10 and R21 to R27 groups each independently are at least one selected from the group consisting of deuterium, a halogen, a (C1-C30)alkyl group substituted or unsubstituted with a halogen, a (C6-C30)aryl group, a 5- to 30-membered heteroaryl group substituted or unsubstituted with a (C6-C30)aryl, a (C3-C30)cycloalkyl group, a 5- to 7-membered heterocycloalkyl group, a (C1-C30)alkyl silyl group, a (C6-C30)aryl silyl group, a (C1-C30)alkyl (C6-C30)aryl silyl group, a (C2-C30)alkenyl group, a (C2-C30)alkynyl group, a cyano group, a carbazolyl group, a (C1-C30)alkyl amino group, a (C6-C30)aryl amino group, a (C1-C30)alkyl (C6-C30)aryl amino group, a (C6-C30)aryl boronyl group, a (C1-C30)alkyl boronyl, a (C1-C30)alkyl (C6-C30)aryl boronyl, a (C6-C30)aryl (C1-C30)alkyl group, a (C1-C30)alkyl (C6-C30)aryl group, a carbonyl group, a carboxyl group, a nitro group and a hydroxyl group.
  3. The compound according to claim 1, characterized in that X₁ represents CH or N; and L₁ and L₂ each independently is selected from the group consisting of a single bond, phenylene, naphthylene, biphenylene, terphenylene, anthrylene, andenylene, fluorenylene, phenanthrylene, triphenylenylene, pyrenylene, phenylenylene, chrysenylene, naphthasenylene, fluorantenyl, furylene, thiophenylene, pyrrolylene, imidazolylene, pyrazolylene, thiazolylene, thiadiazolylene, isothiazolylene, isoxazolylene, oxazolylene, oxadiazolylene, triazinylene, tetrazinylene, triazolylene, tetrazolylene, furazanylene, pyridylene, pyrazinylene, pyrimidinylene, pyridazinylene, benzofuranylene, benzothiophenylene, isobenzofuranylene, benzoimidazolylene, benzothiazolylene, benzoisothiazolylene, benzoisoxazolylene, benzooxazolylene, isoindolylene, indolylene, indazolylene, benzothiadiazolylene, quinolylene, isoquinolylene, cinnolinylene, quinazolinylene, quinoxalinylene, carbazolylene, phenanthridinylene, benzodioxolylene, dibenzofuranylene and dibenzothiophenylene.
  4. The compound according to claim 1, characterized in that in formula 1 is selected from the following structures:
  5. The compound according to claim 1, characterized in that the compound represented by formula 1 is selected from the group consisting of:
  6. An organic electroluminescent device comprising the compound according to claim 1.
EP12771699.1A 2011-04-12 2012-04-12 NOVEL COMPOUND FOR ORGANIC ELECTRONIC MATERIAL AND ORGANIC ELECTROLUMINESCENT DEVICE USING THE SAME Withdrawn EP2697216A4 (en)

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