TW201307353A - Novel organic electroluminescence compounds and organic electroluminescence device using the same - Google Patents

Abstract

The present invention relates to novel organic electroluminescence compounds and an organic electroluminescence device containing the same. The compounds according to the present invention have high luminous efficiency and long operation lifetime. Therefore, they can produce an organic electroluminescence device having enhanced power consumption efficiency.

Description

Novel organic electroluminescent compound and organic electric field illuminating device using the same

The present invention relates to novel organic electroluminescent compounds and organic electroluminescent devices using the same.

Electroluminescent (EL) devices are self-illuminating devices that have the advantage of providing a wider viewing angle, a higher contrast ratio, and faster reaction times than other types of display devices. Eastman Kodak first developed an organic EL device that forms a luminescent material by using a small molecule, which is an aromatic diamine and an aluminum complex [Appl. Phys. Lett. 51, 913, 1987].

The most important factor determining the luminous efficiency of an organic EL device is a luminescent material. Fluorescent materials have been widely used as luminescent materials to date. However, from the standpoint of the electric field luminescence mechanism, the development of phosphorescent materials is one of the best ways to theoretically increase the luminous efficiency by a factor of four. The ruthenium (III) complex is a well-known phosphorescent material comprising bis(2-(2'-benzothienyl)-pyridine-N,C3') oxime (acetamidacetone) [(acac)Ir ( Btp) ₂ ], ginseng (2-phenylpyridine) fluorene [Ir(ppy) ₃ ] and bis(4,6-difluorophenylpyridine-N,C 2 )methylpyridinium (Firpic), respectively, as red light, Green light and blue light materials. In particular, many phosphorescent materials have recently been studied in Japan, Europe, and the United States.

Up to now, 4,4'-N,N'-dicarbazole-biphenyl (CBP) is the most widely known host material for phosphorescent materials. Furthermore, it is known to use bathocuproine (BCP) and bis(2-methyl-8-hydroxyquinoline) (4-phenylphenol) aluminum (III) (BAlq) as a hole blocking layer (hole blocking). Layer) The organic EL device, and Pioneer et al. have developed a high-performance organic EL device using a BAlq derivative as a host material.

Although these materials provide good luminescent properties, they still have the following disadvantages: degradation may occur during vacuum high temperature deposition processes because of their low glass transition temperature and poor thermal stability. The power efficiency of the organic EL device is defined by the following formula: [(Π/voltage) × current efficiency], and the power efficiency is inversely proportional to the voltage, so it is necessary to improve power efficiency to reduce power consumption. Although organic EL devices including phosphorescent materials provide higher current efficiency (candle/amperes, cd/A) than those including phosphor materials, organic EL devices using conventional phosphorescent materials (such as BAlq or CBP) use fluorescence. The organic EL device of the material has a high driving voltage. Therefore, an organic EL device using a conventional phosphorescent material has no advantage in power efficiency (lumens/watt, lm/W). Furthermore, the organic EL device has a short operational life.

Korean Patent No. KR0948700 discloses an aryl carbazole compound as a compound for an organic EL device, which is substituted with a heteroaryl group including a nitrogen atom. However, it does not disclose a fused carbazole compound which is attached directly or indirectly to its heterophenyl group substituted with a biphenyl or a terphenyl group at its nitrogen position.

It is an object of the present invention to provide a compound for organic electric field luminescence which imparts high luminous efficiency and long operational life to a device and has suitable color coordinates; and an organic electric field illuminating device using the compound as a luminescent material, which has high efficiency And long life.

The inventors of the present invention have found that the above object can be achieved by the compound represented by the following formula (1):

Wherein L ₁ represents a single bond, a substituted or unsubstituted 3 to 30 membered heteroaryl group, a substituted or unsubstituted (C6-C30) extended aryl group, or a substituted or unsubstituted group (C3) -C30)cycloalkyl group; X ₁ and X ₂ each independently represent CH or N; Y ₁ and Y ₂ each independently represent -O-, -S-, -CR ₅ R ₆ - or -NR ₇ -, restrictions Y ₁ and Y _{2 are} not present at the same time; Ar ₁ and Ar ₂ each independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) An aryl group, or a substituted or unsubstituted 3 to 30 membered heteroaryl; each of R ₁ to R ₄ independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, Substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted 3 to 30 membered heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted Substituted 5- to 7-membered heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl (C1-C30) alkyl, -NR ₁₁ R ₁₂ , -SiR ₁₃ R ₁₄ R ₁₅ , -SR ₁₆ , -OR ₁₇ , cyano, nitro, or hydroxy; or R ₁ to R ₄ bonded to one or more adjacent substituents to form a monocyclic or polycyclic ring (C5-C30) an alicyclic or aromatic ring, and one or more carbon atoms of the ring may be substituted with at least one hetero atom selected from the group consisting of nitrogen, oxygen and sulfur; R ₅ to R ₇ and R ₁₁ to R ₁₇ each Independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted 3 to 30 member Aryl, substituted or unsubstituted 5 to 7 membered heterocycloalkyl, or substituted or unsubstituted (C3-C30)cycloalkyl; or R ₅ to R ₇ and R ₁₁ to R ₁₇ bonded Adjacent to one or more substituents to form a monocyclic or polycyclic (C5-C30) alicyclic or aromatic ring, and one or more carbon atoms of the ring may be selected from at least one selected from the group consisting of nitrogen, oxygen, and sulfur a hetero atom substitution; a, b, c and d each independently represent an integer from 1 to 4; when a, b, c or d is an integer of 2 or more, each R ₁ , each R ₂ , each R ₃ or each R ₄ is the same or different; the heterocycloalkyl group and the (hetero)heteroaryl group contain at least one selected from the group consisting of B, N, O, S, P(=O), Si and P atom.

The organic electroluminescent compound of the present invention can produce an organic electric field light-emitting device having high luminous efficiency and long operational life.

Further, since the compound of the present invention has high electron transport efficiency, crystallization can be prevented when the device is manufactured. Furthermore, the compound has good layering properties and improves the current characteristics of the device. Therefore, it is possible to manufacture an organic electric field light-emitting device having a reduced driving voltage and improved power efficiency.

The invention will be described in detail hereinafter. However, the following description is intended to be illustrative of the invention and is not intended to limit the scope of the invention in any way.

The present invention relates to an organic electroluminescent compound represented by the above formula (1), and an organic electric field light-emitting device comprising the same.

In the present specification, "(C1-C30)(alkyl)alkyl" means a straight or branched alkyl group having 1 to 30 carbon atoms, wherein the number of the carbon atoms is preferably from 1 to 20 More preferably, it is 1 to 10, and includes methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, etc.; "(C2-C30) alkenyl" means a linear or branched alkenyl group having 2 to 30 carbon atoms, wherein the number of the carbon atoms is preferably 2 to 20, more preferably 2 to 10, and includes a vinyl group, a 1-propenyl group, and 2 Propylene, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, etc.; "(C2-C30)alkynyl" has 2 to 30 carbon atoms a linear or branched alkynyl group, wherein the number of carbon atoms is preferably from 2 to 20, more preferably from 2 to 10, and includes ethynyl, 1-propynyl, 2-propynyl, 1- Butynyl, 2-butynyl, 3-butynyl, 1-methylpentan-2-ylalkynyl, etc.; "(C3-C30)cycloalkyl" is a single ring having 3 to 30 carbon atoms Or a polycyclic hydrocarbon, wherein the number of the carbon atoms is preferably from 3 to 20, more preferably from 3 to 7, and comprises a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group. "3 to 7 membered heterocycloalkyl" has at least one hetero atom selected from B, N, O, S, P(=O), Si and P (preferably O, S and N), and 3 a cycloalkyl group to a 7-ring main chain atom, and comprising tetrahydrofuran, pyrrolidine, thiolan, tetrahydropyran, etc.; "(C6-C30) (extended) aryl" is derived from having 6 to 30 a monocyclic or fused ring of an aromatic hydrocarbon having one carbon atom, wherein the number of the carbon atoms is preferably from 6 to 20, more preferably from 6 to 15, and includes a phenyl group, a biphenyl group, a triphenyl group, Naphthyl, anthryl, phenanthryl, anthracenyl, fluorenyl, triphenylenyl, fluorenyl, tetracenyl, fluorenyl, chrysenyl, naphthacenyl , fluoranthenyl, etc.; "3 to 30 members (extended) heteroaryl" having at least one (preferably 1 to 4) selected from the group consisting of B, N, O, S, P ( a hetero atom of a group consisting of: O), Si, and P, and an aryl group of 3 to 30 ring main chain atoms; a monocyclic ring or a condensed ring condensed with at least one benzene ring; preferably 5 to 20 More preferably 5 to 15 ring backbone atoms; may be partially saturated; One less heteroaryl or aryl group formed by one or more single bonds bonded to a heteroaryl group; and comprises a monocyclic type heteroaryl group, including furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl , thiazolyl, thiadiazolyl, isothiazolyl, iso Azolyl, Azolyl, Diazolyl, three Base, four Base, triazolyl, tetrazolyl, furazolyl, pyridyl, pyridyl Base, pyrimidinyl, oxime Base, and fused ring type heteroaryl, including benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl Benzoisothiazolyl, benzopyrene Azolyl, benzo Azyl, isodecyl, fluorenyl, oxazolyl, benzothiadiazolyl, quinolinyl, isoquinolyl, cinnolinyl, quinazolinyl, quin Orolinyl, carbazolyl, brown Peptidyl, benzodiyl Benzodioxolyl and the like. Further, "halogen" includes F, Cl, Br, and I.

In the present specification, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom of a certain functional group passes through another atom or group (also That is, the substituent is substituted.

In the formula (1), a substituted alkyl group, a substituted (extended) aryl group, a substituted (extended) group of L ₁ , Ar ₁ , Ar ₂ , R ₁ to R ₇ and R ₁₁ to R ₁₇ groups And the substituents of the substituted arylalkyl group, the substituted heterocycloalkyl group and the substituted aralkyl group are each independently selected from the group consisting of: hydrazine, Halogen, halogen-substituted or unsubstituted (C1-C30) alkyl, (C6-C30) aryl, substituted by (C1-C30) alkyl or (C6-C30) aryl or unsubstituted 3 to 30-membered heteroaryl, (C3-C30)cycloalkyl, 5- to 7-membered heterocycloalkyl, tri(C1-C30)alkyldecyl, tris(C6-C30)aryldecyl,di(C1- C30) alkyl (C6-C30) aryldecyl, (C1-C30)alkylbis(C6-C30)aryldecyl, (C2-C30)alkenyl, (C2-C30)alkynyl, cyano , N-carbazolyl, di(C1-C30)alkylamino, di(C6-C30)arylamino, (C1-C30)alkyl(C6-C30)arylamino, di(C6- C30) aryl boron carbonyl, di(C1-C30)alkyl boroncarbonyl, (C1-C30)alkyl (C6-C30) aryl boroncarbonyl, (C6-C30) aryl (C1-C30) alkyl, (C1-C30)alkyl (C6-C30) aryl, carboxyl, nitro, and hydroxy, preferably selected from the group consisting of At least one of the group consisting of: hydrazine, halogen, (C1-C6) alkyl, (C6-C20) aryl, and di(C6-C20) arylamine, more preferably selected from the group consisting of At least one of the group: hydrazine, fluorine, methyl, phenyl, and diphenylamino.

In the above formula (1), L ₁ represents a single bond, a 3 to 30 member heteroaryl group or a (C6-C30) extended aryl group; X ₁ and X ₂ each independently represent CH or N; Y ₁ and Y ₂ Each independently represents -O-, -S-, -CR ₅ R ₆ - or -NR ₇ -, and the restrictions are that Y ₁ and Y _{2 are} not present at the same time; Ar ₁ and Ar ₂ each independently represent hydrogen, deuterium, halogen, ( C1-C30)alkyl, (C6-C30)aryl, or 3 to 30 membered heteroaryl; R ₁ to R ₄ each independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl, (C6-C30 An aryl group, a 3 to 30 membered heteroaryl group, a carbazolyl group, or -SiR ₁₃ R ₁₄ R ₁₅ ; or R ₄ bonded to one or more adjacent substituents to form a monocyclic or polycyclic ring (C5) -C30) an alicyclic or aromatic ring, and one or more carbon atoms of the ring may be substituted with at least one hetero atom selected from the group consisting of nitrogen, oxygen and sulfur; R ₅ to R ₇ each independently represent a (C1-C30) alkyl group. , (C6-C30) aryl, or 3 to 30 membered heteroaryl; or R ₅ and R ₆ are bonded to each other to form a monocyclic or polycyclic (C5-C30) alicyclic or aromatic ring, and the ring One or more carbon atoms may be replaced by at least one hetero atom selected from the group consisting of nitrogen, oxygen and sulfur; R ₁₃ to R ₁₅ each independently represent (C1-C30)alkyl, (C6-C30)aryl, or 3 to 30 members of the mixed ; And L ₁ and the arylene group extending heteroaryl in Ar ₁ and Ar ₂ of the alkyl group, aryl group, heteroaryl group and carbazolyl group, and in R ₁ to R ₇ and R ₁₃ to R ₁₅ of The alkyl, aryl and heteroaryl groups may be substituted by at least one selected from the group consisting of hydrazine, halogen, halogen-substituted or unsubstituted (C1-C30) alkyl, (C6-C30) aryl 3- to 30-membered heteroaryl, (C3-C30)cycloalkyl, tri(C1-C30)alkylnonane substituted or unsubstituted with (C1-C30)alkyl or (C6-C30)aryl , tris(C6-C30)arylalkylene, di(C1-C30)alkyl(C6-C30)aryldecyl,(C1-C30)alkylbis(C6-C30)aryldecyl,fluorene Azyl, bis(C1-C30)alkylamino, bis(C6-C30)arylamino, (C1-C30)alkyl(C6-C30)arylamino, (C6-C30)aryl C1-C30) alkyl, and (C1-C30)alkyl (C6-C30) aryl.

In the above formula (1), L _{1 is} preferably a single bond or a (C1-C6) alkyl substituted or unsubstituted (C6-C20) extended aryl group, more preferably a single bond, a phenyl group, Or a phenyl group substituted by a methyl group.

Y ₁ and Y ₂ each independently represent -O-, -S-, -CR ₅ R ₆ - or -NR ₇ -, wherein R ₅ to R _{7 are} each independently preferably unsubstituted (C1-C6) alkane. Or an unsubstituted (C6-C20) aryl group, or Y ₁ and Y ₂ bonded together to form a monocyclic or polycyclic (C5-C20) alicyclic or aromatic ring, preferably Y ₁ and Y ₂ It is a methyl, phenyl or spiro bond.

Ar ₁ and Ar _{2 are} each independently preferably hydrogen; halogen; unsubstituted (C1-C6) alkyl; substituted or unsubstituted (C6-C20) aryl by hydrazine, halogen or (C1-C6)alkyl Or an unsubstituted 5 to 15 membered heteroaryl; more preferably hydrogen, fluorine, methyl, phenyl, phenyl substituted by fluorene, phenyl substituted by fluorine, naphthyl, biphenyl, A methyl substituted sulfhydryl group or a carbazolyl group.

R ₁ to R _{4 are} each independently hydrogen, unsubstituted (C1-C6)alkyl, substituted or unsubstituted (C6-C20) aryl by di(C6-C20)arylamino group, Substituted 5 to 15 membered heteroaryl, or -SiR ₁₃ R ₁₄ R ₁₅ , or R ₁ to R ₄ bonded to one or more adjacent substituents to form a monocyclic or polycyclic ring (C5-C30) An alicyclic or aromatic ring, more preferably hydrogen, methyl, phenyl, phenyl substituted with diphenylamine, carbazolyl or triphenylsulfanyl, or phenyl substituted with fluoro, naphthyl And a biphenyl group, a methyl-substituted fluorenyl group, or a carbazolyl group; or a bond to an adjacent one or more substituents to form a monocyclic or polycyclic (C5-C30) alicyclic or aromatic ring.

R ₁₁ to R _{17 are} each independently preferably an unsubstituted (C6-C20) aryl group, more preferably a phenyl group.

In the above formula (1), it is preferred that the L ₁ is a single bond or a (C1-C6)alkyl substituted or unsubstituted (C6-C20) extended aryl group; and X ₁ and X _{2 are} each independently represented. CH or N; Y ₁ and Y ₂ each independently represent -O-, -S-, -CR ₅ R ₆ - or -NR ₇ -, wherein R ₅ to R ₇ each independently represent unsubstituted (C1-C6 An alkyl or unsubstituted (C6-C20) aryl group; Ar ₁ and Ar ₂ each independently represent hydrogen; halogen; unsubstituted (C1-C6) alkyl; oxime, halogen or (C1-C6) Alkyl-substituted or unsubstituted (C6-C20) aryl; or unsubstituted 5 to 15 membered heteroaryl; R ₁ to R ₄ each independently represent hydrogen, unsubstituted (C1-C6) alkyl a (C6-C20) aryl group substituted or unsubstituted with a bis(C6-C20)arylamino group, an unsubstituted 5 to 15 membered heteroaryl group, or -SiR ₁₃ R ₁₄ R ₁₅ ; or R ₁ And R _{4 is} bonded to one or more adjacent substituents to form a monocyclic or polycyclic (C5-C30) alicyclic or aromatic ring, wherein R ₁₃ to R ₁₅ each independently represent unsubstituted (C6 -C20) aryl.

More specifically, L ₁ represents a single bond, a phenyl group, a phenyl group, a triphenyl group, a fluorene group, a hydrazine group, a stretched triphenyl group, a hydrazine group, a hydrazine group, and a hydrazine group. Base, thickened tetraphenyl, acrodiene thiol, thienyl, thyrrolyl, pyrazolyl, thiazolyl, extens Azolyl Diazolyl, stretched three Base, stretch four , triazole, exofuran, pyridyl, benzofuranyl, benzothiophene, decyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl Benzene Azolyl Azolyl, benzothiadiazolyl, dibenzofuranyl or dibenzothiophenyl; Ar ₁ and Ar ₂ each independently represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl , isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-decyl, decyl, dodecyl, hexadecanyl, Trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, biphenyl, anthryl, alkadienyl, triphenyl, fluorenyl, Mercapto, fused tetraphenyl, fluorenyl, pyridyl, pyrrolyl, furyl, thienyl, imidazolyl, benzimidazolyl, quinolyl, tri Base, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothiophenyl, pyrazolyl, fluorenyl, oxazolyl, thiazolyl, Azolyl, benzothiazolyl, benzo Azyl, morpholinyl, quin a phenyl group, or an N-carbazolyl group; each of R ₁ to R ₄ independently represents hydrogen, deuterium, chloro, fluoro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, Tertiary butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, n-octyl, 2-ethylhexyl, n-decyl, decyl, dodecyl, hexadecanyl, trifluoromethyl, Perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluorobutyl, phenyl, naphthyl, anthryl, biphenyl, anthracenyl, allyldienyl, orthotriphenyl , mercapto, fluorenyl, fused tetraphenyl, fluorenyl, pyridyl, pyrrolyl, furyl, thienyl, imidazolyl, benzimidazolyl, fluorenyl, pyridyl Base, pyrimidinyl, oxime Base, quinolyl, three Base, benzofuranyl, dibenzofuranyl, benzothienyl, dibenzothiophenyl, pyrazolyl, fluorenyl, oxazolyl, thiazolyl, Azolyl, benzothiazolyl, benzo Azyl, morpholinyl, trimethyldecyl, triethyldecyl, tripropyldecyl, tris(t-butyl)decyl, tert-butyldimethylalkyl, dimethylphenyl a decyl group, a methyldiphenyl fluorenyl group or a triphenyl fluorenyl group; the substituents of the L ₁ , Ar ₁ , Ar ₂ and R ₁ to R ₄ each independently may be at least one selected from the group consisting of the following Replace: hydrazine, chloro, fluoro, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, positive Heptyl, n-octyl, 2-ethylhexyl, n-decyl, decyl, dodecyl, hexadecyl, trifluoromethyl, perfluoroethyl, trifluoroethyl, perfluoropropyl, perfluoro Butyl, phenyl, naphthyl, biphenyl, 9,9-dimethylindenyl, 9,9-diphenylfluorenyl, allyldienyl, tert-triphenyl, anthracenyl, fluorenyl , thick tetraphenyl, decyl, dimethylamino, diethylamino, methylphenylamino, diphenylamino, trimethyldecyl, triethyldecyl, tripropyldecane Base, tris(t-butyl)decyl, tert-butyldimethylalkyl, dimethyl Silicon phenyl group, diphenyl methyl group silicon, silicon triphenyl group, N- phenyl-N- carbazolyl group and a carbazolyl group.

In the above (1), Some are selected from the following structures, but are not limited to this:

Wherein R ₅ , R ₆ and R _{7 are} as defined in the formula (1).

Representative compounds of the invention comprise the following compounds:

The organic electroluminescent compound of the present invention can be prepared according to the following reaction scheme.

Wherein, L ₁ , Ar ₁ , Ar ₂ , X ₁ , X ₂ , Y ₁ , Y ₂ , R ₁ to R ₄ , a, b, c and d are defined as defined in the above formula (1), and Hal represents halogen.

Further, the present invention provides an organic electric field light-emitting device comprising the compound of the formula (1). The organic electric field light-emitting device includes a first electrode, a second electrode, and at least one organic layer interposed between the first electrode and the second electrode. The organic layer comprises at least one compound of the formula (1) of the present invention. Furthermore, the organic layer comprises a light-emitting layer, wherein the light-emitting layer comprises a compound of the formula (1) as a host material.

Further, a phosphorescent dopant for use in an organic electric field light-emitting device together with the host material of the present invention may be selected from compounds represented by the following formula (2): M ¹ L ¹⁰¹ L ¹⁰² L ¹⁰³ ---(2)

Wherein, M ¹ is selected from the group consisting of Ir, Pt, Pd and Os; 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, unsubstituted or substituted by one or more halogen (C1-C30) alkyl groups, unsubstituted or substituted by one or more (C1-C30) alkyl groups. (C6-C30) aryl, or halogen; R ₂₀₄ to R ₂₁₉ each independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C1-C30) Alkoxy, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted (C2-C30)alkenyl, substituted or unsubstituted (C6-C30) aryl, Substituted or unsubstituted mono or di(C1-C30)alkylamino, substituted or unsubstituted mono or di(C6-C30)arylamino, SF ₅ , substituted or unsubstituted Tri(C1-C30)alkyldecane, substituted or unsubstituted bis(C1-C30)alkyl(C6-C30)aryldecyl, substituted or unsubstituted tris(C6-C30)aryl Alkyl, cyano or halogen; R ₂₂₀ to R ₂₂₃ each independently represent hydrogen, deuterium, unsubstituted or substituted by one or more halo (C1-C30) alkyl groups, or unsubstituted or via one or more a (C1-C30) alkyl substituent of (C6-C30) aryl; R ₂₂₄ and R ₂₂₅ each independently represents hydrogen, , Substituted or non-substituted (C1-C30) alkyl, substituted or non-substituted (C6-C30) aryl, or halogen; or R ₂₂₄ and R ₂₂₅ bonded to one or more of the adjacent a substituent to form a monocyclic or polycyclic (C5-C30) alicyclic or aromatic ring; R ₂₂₆ represents a substituted or unsubstituted (C1-C30) alkyl group, substituted or unsubstituted (C6-C30 Aryl, substituted or unsubstituted 5 or 30 membered heteroaryl or halogen; R ₂₂₇ to R ₂₂₉ each independently represent hydrogen, deuterium, substituted or unsubstituted (C1-C30) alkyl, substituted Or unsubstituted (C6-C30) aryl or halogen; Q represents ; R ₂₃₁ to R ₂₄₂ each independently represent hydrogen, deuterium, unsubstituted or substituted by one or more halogens (C1-C30)alkyl, (C1-C30) alkoxy, halogen, substituted or unsubstituted (C6-C30) aryl, cyano, or substituted or unsubstituted (C5-C30) cycloalkyl; or each R ₂₃₁ to R ₂₄₂ permeable to alkyl or alkenyl bonded to the phase The ortho substituent is formed to form a spiro or fused ring or is permeable to an alkyl or alkenyl group to R ₂₀₇ or R ₂₀₈ to form a saturated or unsaturated fused ring.

The dopant of the formula (2) includes the following, but is not limited thereto:

The organic electroluminescence device of the present invention may further comprise at least one compound selected from the group consisting of an arylamine-based compound and a styrylarylamine-based compound, in addition to the compound represented by the formula (1).

In the organic electric field light-emitting device of the present invention, the organic layer may further comprise a metal selected from Group 1 of the periodic table, a metal of the second group, a transition metal of the fourth cycle, a transition metal of the fifth cycle, and a lanthanide metal. And at least one metal of the group consisting of organometallics of the d-group plating element, or at least one complex of the metal. The organic layer may include a light emitting layer and a charge generating layer.

Furthermore, in addition to the compound of the present invention, the organic electroluminescent device may comprise at least one luminescent layer comprising a blue electric field luminescent compound, a red electric field luminescent compound or a green electric field luminescent compound to emit white light.

Preferably, in the organic electroluminescence device of the present invention, at least one layer selected from the group consisting of a chalcogenide layer, a metal halide layer, and a metal oxide layer (hereinafter referred to as "surface layer") may be provided. On one or more inner surfaces of a single or two electrodes. Specifically, it is preferable to provide a layer of a chalcogen compound (including an oxide) of bismuth or aluminum on the anode surface of the electric field luminescent medium layer, and to provide a metal halide layer or a metal oxide layer on the luminescent medium layer. On the surface of the cathode. The surface layers provide operational stability of the organic electric field illuminating device. Preferably, the chalcogen compound comprises SiO _X (1≦X≦2), AlO _X (1≦X≦1.5), SiON, SiAlON, etc.; the metal halide comprises LiF, MgF ₂ , CaF ₂ , rare earth metal fluoride And a metal oxide containing Cs ₂ O, Li ₂ O, MgO, SrO, BaO, CaO, or the like.

Preferably, in the organic electric field light-emitting device of the present invention, a mixing region of the electron transporting compound and the reducing dopant, or a mixture of the hole transporting compound and the oxidizing dopant may be disposed on at least one surface of the electrode pair. Area. In this case, the electron transporting compound is reduced to an anion, making it easy to inject and transport electrons from the mixing zone to the electric field illuminating medium. Furthermore, the hole transport compound is oxidized to a cation such that it is easy to inject and transport holes from the mixing zone to the electric field illuminating medium. Preferably, the oxidizing dopant comprises a plurality of Lewis acids and acceptor compounds; and the reducing dopant comprises an alkali metal, an alkali metal compound, an alkaline earth metal, a rare earth metal, and a mixture thereof. A reductive doping layer can be used as the charge generating layer to prepare an electric field illuminating device having two or more layers of an electroluminescent layer and emitting white light.

Hereinafter, the organic electroluminescent compound, the preparation method of the compound, and the luminescent properties of the device including the compound of the present invention will be described in detail with reference to the following examples:

Example 1: Preparation of Compound C-55

Preparation of Compound 1-1

Mix 2-bromo-9,9-dimethyl-9H-indole (50 g (g), 0.183 mol (mol)), 2-chloroaniline (57 ml (ml), 0.549 mol), Pd (OAc) ₂ (1.6 g, 0.007 mol), P(t-Bu) ₃ (7.2 ml, 0.0146 mol), NaOt-Bu (44 g, 0.458 mol) and toluene (500 ml), stirred at 120 ° C The reaction mixture was allowed to stand for 12 hours. After the reaction was terminated, the reaction mixture was extracted with ethyl acetate (EA). The obtained organic layer was dried (MgSO ₄ ), filtered, evaporated, evaporated,

Preparation of Compound 1-2

Mixed compound 1-1 (32 g, 0.1 mol), Pd(OAc) ₂ (1.1 g, 0.005 mol), di-t-butyl(methyl)phosphonium tetrafluoroborate (2.48 g, 0.01 mol) After K ₂ CO ₃ (42 g, 0.30 mol) and DMA (550 ml), the reaction mixture was stirred at 200 ° C for 12 hours. After the reaction was terminated, the reaction mixture was extracted with EA. The organic layer was dried over MgSO ₄ of the resulting, filtered, evaporated under reduced pressure to remove the solvent, and was filtered through column to give compound 1-2 (14 g, 47%).

Preparation of Compound 1-3

Mix 9,9-dimethylindole-2-boronic acid (30 g, 126.0 mmol (mmol)), 1,3-dibromobenzene (30.45 ml, 252.00 mmol), PdCl ₂ (PPh ₃ ) ₂ ( After 2.6 g, 3.78 mmol, 2M Na ₂ CO ₃ (160 mL) and toluene (500 mL), the reaction mixture was heated at 100 °C. After 5 hours, the reaction mixture was cooled to room temperature, extracted with EA, washed with distilled water, dried over MgSO _4, filtered, evaporated under reduced pressure to remove the solvent, and was filtered through column to give compound 1-3 (80 g , 67.46%).

Preparation of compound 1-4

Compound 1-3 (30 g, 85.89 mmol) was dissolved in tetrahydrofuran (THF) (500 ml), and a solution of 2.5 M n-butyllithium (n-BuLi) in hexane (41.23 ml) was added at -78 °C. After 103.07 mmoles to the reaction mixture, the reaction mixture was stirred for 1 hour. The reaction mixture was stirred at room temperature for 12 hours with the slow addition of B(OMe) ₃ (14.36 mL, 128.84 mmol) to the reaction mixture and slowly increasing temperature. After extraction with EA, the obtained organic layer was dried over anhydrous MgSO ₄ to remove residual water, distilled under reduced pressure to remove solvent, and recrystallized from EA and hexane to give compound 1-4 (24 g, 68.93%) .

Preparation of compound 1-5

Mix 2,4-dichloropyrimidine (7 g, 46.98 mmol), compound 1-4 (16.2 g, 51.68 mmol), Pd(PPh ₃ ) ₄ (1.62 g, 1.40 mmol), 2M Na _{After 2} CO ₃ (60 ml) and dimethyl ether (DME) (400 ml), the reaction mixture was stirred at 90 °C. After 4 hours, the reaction mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with EA. The obtained organic layer was dried over anhydrous MgSO ₄ to remove residual water, distilled under reduced pressure to remove solvent, and filtered through a column to obtain compound 1-5 (14 g, 77.83%).

Preparation of Compound C-55

After compound 1-2 (4.5 g, 15.89 mmol) and compound 1-5 (7.3 g, 19.07 mmol) were dissolved in dimethylformamide (DMF) (130 ml), 60% NaH ( In mineral oil, 0.76 g, 19.07 mmol was slowly added to the mixture and stirred at room temperature for 12 hours. After the reaction was terminated, MeOH was added to the reaction mixture. Filter the resulting by gelatin The solid was recrystallized from EA and DMF to afford compound C-55 (l.

MS/FAB measured value 630; calculated value 629.79

Example 2: Preparation of Compound C-56

Preparation of Compound 2-1

Mix 3-triphenylboronic acid (8.2 g, 29.9 mmol), 2,4-dichloropyrimidine (6.6 g, 44.9 mmol), Pd(PPh ₃ ) ₄ (1.7 g, 1.5 mmol) After Na ₂ CO ₃ (7.9 g, 74.8 mmol), toluene (100 ml), EtOH (25 ml) and purified water (25 ml), the reaction mixture was stirred under reflux for 5 hours. After the reaction was terminated, the reaction mixture was cooled to room temperature and filtered. The obtained organic layer was dried with MgSO ₄ The residual solution was concentrated under reduced pressure to give Compound 2-1 (7 g, 70%).

Preparation of Compound C-56

After dissolving Compound 1-2 (3.27 g, 11.5 mmol) in DMF (80 mL), NaH (507 mg, 12.7 mmol) was added at 0 ° C and stirred for 10 min. Compound 2-1 (4.2 g, 12.1 mmol) was added to the reaction mixture and stirred for 7 hours. After the reaction was terminated, MeOH was added to the reaction mixture. The obtained solid was filtered through EtOAc (EtOAc) (EtOAc)

MS/FAB measured value 590; calculated value 589.73

Example 3: Preparation of Compound C-67

Preparation of Compound 3-1

Mix 4-dibenzothiopheneboronic acid (10 g, 43.84 mmol), 2-bromonitrobenzene (10.6 g, 52.61 mmol), Pd(PPh ₃ ) ₄ (2.53 g, 2.19 mmol), After 2 M K ₂ CO ₃ (50 ml), toluene (200 ml) and ethanol (50 ml), the reaction mixture was stirred under reflux. After 4 hours, the reaction mixture was cooled to room temperature and distilled water was added and extracted with EA. The obtained organic layer was dried over anhydrous MgSO ₄ to remove residual water, distilled under reduced pressure to remove solvent, and filtered through a column to obtain Compound 3-1 (11 g, 82.17%).

Preparation of Compound 3-2

After mixing compound 3-1 (11 g, 36.02 mmol), P(OEt) ₃ (100 ml) and 1,2-dichlorobenzene (100 ml), the reaction mixture was stirred at 150 ° C under reflux. After 5 hours, the reaction mixture was cooled to room temperature, distilled under reduced pressure, and filtered through a column to afford compound 3-2 (7 g, 25.60 mmol, 71.13%).

Preparation of Compound 3-3

Will 2,4,6-trichloro-1,3,5-three (43.5 g, 236 mmol) After dissolving in THF (230 ml), the reaction mixture was stirred at -78 °C (reaction mixture A). After dissolving compound 3-2 (22 g, 79 mmol) in THF (150 mL), the reaction mixture was taken in NaH (4.7 g, 118 m. After the reaction mixture B was slowly placed in the reaction mixture A, the reaction mixture was stirred for 4 hours. After stirring, distilled water (500 ml) was slowly added, and stirred for 30 minutes. The solid obtained was filtered through column chromatography and recrystallized to give compound 3-3 (31 g, 92%).

Preparation of compound 3-4

Mixed compound 3-3 (12 g, 28 mmol), biphenyl-3-ylboronic acid (6 g, 31 mmol), Na ₂ CO ₃ (8 g, 71 mmol), toluene (370 ml) After distilling water (36 ml) and Pd(PPh ₃ ) ₄ (1 g, 0.9 mmol), the reaction mixture was stirred at 120 °C. After 5 hours, the reaction mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with EA. The obtained organic layer was dried over anhydrous MgSO ₄ to remove residual water and distilled under reduced pressure to remove solvent. The solid obtained was washed with methanol, filtered, dried and filtered and purified by column chromatography to afford compound 3-4 (15 g, 98%).

Preparation of Compound C-67

Mix compound 3-4 (8.5 g, 16 mmol), phenylboronic acid (3 g, 23 mmol), Na ₂ CO ₃ (5 g, 47 mmol), toluene (168 mL), distilled water ( After 24 ml), ethanol (24 ml) and Pd(PPh ₃ ) ₄ (1 g, 0.9 mmol), the reaction mixture was stirred at 120 °C. After 5 hours, the reaction mixture was cooled to room temperature, distilled water was added, and the mixture was extracted with EA. The obtained organic layer was dried over anhydrous MgSO ₄ to remove residual water and distilled under reduced pressure to remove solvent. The obtained solid was washed with methanol, filtered, dried, and filtered and purified by column chromatography to afford Compound C-67 (6.1 g, 66%).

MS/FAB measured value 581; calculated value 580.70

Example 4: Preparation of Compound C-87

Preparation of Compound C-87

After dissolving compound 1-5 (10.5 g, 27.44 mmol) and compound 3-2 (5 g, 18.29 mmol) in DMF (100 mL), 60% NaH (in mineral oil, 1.08 g, 27.44 mmol was slowly added to the mixture and stirred at room temperature for 12 hours. After the reaction was terminated, distilled water was added to the reaction mixture. The obtained solid was filtered under reduced pressure, and the obtained solid was dissolved in CHCl ₃ and filtered through a column to give Compound C-87 (7.5 g, 67.25%).

MS/FAB measured value 620; calculated value 619.78

Example 5: Preparation of Compound C-88

Preparation of Compound C-88

After compound 3-2 (3.5 g, 12.83 mmol) and compound 2-1 (4 g, 11.66 mmol) were dissolved in DMF (150 mL), 60% NaH (in mineral oil, 0.7 g, 17.50 mmol was slowly added to the mixture and stirred at room temperature for 12 hours. After the reaction was terminated, distilled water was added to the reaction mixture. The obtained solid was filtered under reduced pressure, and the obtained solid was washed with EA, DMF and THF to afford Compound C-88 (3.7 g, 49.74%).

MS/FAB measured value 580; calculated value 579.71

Example 6: Preparation of Compound C-91

Preparation of Compound 6-1

Mix 4-dibenzothiopheneboronic acid (40 g, 175.36 mmol), bromobenzene (36.8 ml, 350.73 mmol), Pd(PPh ₃ ) ₄ (4.05 g, 3.50 mmol), 2M Na ₂ CO _{After 3} (220 ml), toluene (600 ml) and ethanol (60 ml), the reaction mixture was stirred at 100 °C. After 3 hours, the reaction mixture was cooled to room temperature and distilled water was added and extracted with EA. The obtained organic layer was dried with MgSO ₄ , filtered, evaporated, evaporated,

Preparation of compound 6-2

Compound 6-1 (35 g, 134.33 mmol) was dissolved in THF (500 mL), and a solution of 2.5 M n-butyllithium in hexane (107.5 mL, 268.8 mmol) was added at -78 °C to the reaction. After the mixture, the reaction mixture was stirred at -78 ° C for 1 hour, heated to room temperature, and stirred for 2 hours. B(OMe) ₃ (41.9 ml, 403.30 mmol) was slowly added at -78 °C, and the mixture was stirred while stirring slowly to room temperature for 12 hours. After extraction with EA, the obtained organic layer was dried over anhydrous MgSO ₄ to remove residual water, distilled under reduced pressure to remove solvent, and recrystallized from chloromethane (MC) and hexane to give compound 6-2 (26 g , 63.78%).

Preparation of Compound 6-3

Compound 6-2 (26 g, 85.47 mmol), 2-bromonitrobenzene (18.9 g, 52.61 mmol), Pd(PPh ₃ ) ₄ (1.9 g, 1.70 mmol), 2M Na ₂ After CO ₃ (100 ml), toluene (250 ml) and ethanol (50 ml), the reaction mixture was stirred under reflux. After 4 hours, the reaction mixture was cooled to room temperature and distilled water was added and extracted with EA. The obtained organic layer was dried (MgSO ₄ ), filtered, evaporated, evaporated,

Preparation of Compound 6-4

After mixing compound 6-3 (32 g, 83.87 mmol), P(OEt) ₃ (200 ml) and 1,2-dichlorobenzene (100 ml), the reaction mixture was stirred at 150 ° C under reflux. After 12 hours, the reaction mixture was cooled to rt.

Preparation of Compound C-91

After dissolving compound 6-4 (4 g, 11.44 mmol) and compound 2-1 (4.7 g, 13.73 mmol) in DMF (190 mL), 60% NaH (in mineral oil, 0.68 g, 17.16 mmol was slowly added to the mixture and stirred at room temperature for 12 hours. After the reaction was terminated, distilled water was added to the reaction mixture. The obtained solid was filtered under reduced pressure, and the obtained solid was washed with EA, DMF and THF to give Compound C-91 (2.0 g, 26.65%).

MS/FAB measured value 656; calculated value 655.81

Example 7: Preparation of Compound C-94

Preparation of Compound 7-1

After preparing a bath at -4 ° C in an aqueous solution of saturated NaCl, nitric acid (1.5 equivalents) was placed in a sulfuric acid solvent, and the temperature of the reaction solvent was allowed to become 0 ° C. 1,3-Dibromobenzene (10 g, 42.4 mmol) was placed in a dropping funnel and added dropwise at no more than 10 °C. After 30 minutes, the reaction mixture was quenched with water. The obtained solid was filtered, washed with purified water several times, and filtered through a column to give Compound 7-1 (7 g, 59%).

Preparation of compound 7-2

Mix 4-biphenylthiopheneboronic acid (41 g, 181 mmol), compound 7-1 (71 g, 254.5 mmol), 2M Na ₂ CO ₃ (270 mL), toluene (900 mL) and ethanol ( After 300 ml), the reaction mixture was stirred under reflux. After 5 hours, the reaction mixture was cooled to room temperature and extracted with EtOAc. The organic layer was dried over MgSO ₄ of the resulting, filtered, evaporated under reduced pressure to remove the solvent, and was filtered through column to give compound 7-2 (34 g, 35%).

Preparation of compound 7-3

After mixing compound 7-2 (34 g, 89.52 mmol), P(OEt) ₃ (350 ml) and 1,2-dichlorobenzene (350 ml), the reaction mixture was stirred at 150 °C. After 7 hours, the reaction mixture was cooled to room temperature, distilled under reduced pressure and then recrystallised from EA to afford compound 7-3 (11 g, 35%).

Preparation of compound 7-4

Place compound 7-3 (7 g, 25.60 mmol), iodobenzene (10.44 g, 51.21 mmol), CuI (2.5 g, 12.80 mmol), K ₃ PO ₄ (16.30 g, 76.82 mmol) After the reaction mixture was heated to 50 ° C, ethylenediamine (1.72 mL, 25.60 mmol) was added and stirred under reflux. After 12 hours, the reaction mixture was cooled to room temperature, extracted with EA to aqueous NaHCO _3, dried over MgSO _4, filtered, evaporated under reduced pressure to remove the solvent, and was filtered through column to give compound 7-4 ( 8 grams, 89.41%).

Preparation of Compound C-94

After dissolving NaH (600 mg) in DMF (40 ml), the solution was stirred. After dissolving compound 7-4 (3.5 g, 10.015 mmol) in DME (30 ml), this solution was added to the above-mentioned NaH solution, and stirred for 1 hour. Compound 2-1 (4.1 g, 12.0189 mmol) was dissolved in DMF (30 ml), and after stirring, a mixed solution of compound 7-4 was added to a mixed solution of compound 2-1, and stirred for 12 hours. After the reaction was terminated, pure water was added to the reaction mixture. The resulting solid was filtered and filtered through a pad to afford compound C-94 (3 g, 34%).

MS/FAB measured value 656; calculated value 655.81

Example 8: Preparation of Compound C-96

Preparation of Compound 8-1

Mix 2,5-dibromonitrobenzene (30 g, 106.8 mmol), dibenzothiophen-4-ylboronic acid (20.3 g, 88.9 mmol), Pd(PPh ₃ ) ₄ (5.1 g, 4.45 After mM, Na ₂ CO ₃ (27.9 g, 267 mmol), toluene (600 mL) and EtOH (100 mL), the reaction mixture was stirred at 90 ° C for 3 hours. Purified water was slowly added after stirring to terminate the reaction. The reaction mixture was extracted with EA. The obtained organic layer was dried (MgSO ₄ ), filtered, evaporated

Preparation of Compound 8-2

Compound 8-1 (23 g, 59.85 mmol), phenylboronic acid (8.8 g, 71.83 mmol), Pd(PPh ₃ ) ₄ (3.46 g, 2.99 mmol), Na ₂ CO ₃ (19) After gram, 179.5 mmol, toluene (180 mL) and EtOH (90 mL), the reaction mixture was stirred at 120 ° C for 3 hr. Purified water was slowly added after stirring to terminate the reaction. The reaction mixture was extracted with EA. The obtained organic layer was dried with MgSO ₄ , filtered, evaporated, evaporated,

Preparation of Compound 8-3

After mixing compound 8-2 (15 g, 39.3 mmol) and P(OEt) ₃ (150 ml), the reaction mixture was stirred at 150 ° C for 24 hours. After stirring, the residual solvent was removed using a distillation column, and the reaction mixture was filtered through a column to afford compound 8-3 (6 g, 46%).

Preparation of Compound C-96

After dissolving NaH (1 g, 30.6 mmol) in DMF (20 mL), the solution was stirred. After dissolving Compound 8-3 (8.56 g, 24.5 mmol) in DMF (300 mL), this solution was added to a NaH solution and stirred for 1 hour. Compound 2-1 (7 g, 20.4 mmol) was dissolved in DMF (250 ml), and after stirring, a mixed solution of compound 8-3 was added to a mixed solution of compound 2-1, and stirred for 12 hours. After the reaction was terminated, purified water was added to the reaction mixture. The resulting solid was filtered and filtered through a pad to afford compound C-96 (8.9 g, 67%).

MS/FAB measured value 656; calculated value 655.81

Example 9: Preparation of Compound C-97

Preparation of Compound 9-1

Place dibenzo[ b,d ]furan-4-ylboronic acid (20 g, 94.3 mmol), 2-bromonitrobenzene (17 g, 84.9 mmol), Pd(PPh ₃ ) ₄ (4.9 g After stirring 4.20 mmol, K ₂ CO ₃ (23.5 g, 169.8 mmol), toluene (100 ml), EtOH (50 ml), and purified water (50 ml), the reaction mixture was stirred under reflux 3 hour. After the reaction was terminated, the reaction mixture was cooled to room temperature, the aqueous layer was removed, and the organic layer was dried with MgSO ₄ , filtered and evaporated to remove solvent and filtered through silica gel. The residual solution was concentrated under reduced pressure to give Compound 9-1 (24 g, 98%).

Preparation of Compound 9-2

After compound 9-1 (24 g, 83.0 mmol), PPh ₃ (65 g, 248.9 mmol) and 1,2-dichlorobenzene (250 ml), the mixture was stirred under reflux for 18 hours. After the reaction was terminated, the reaction mixture was cooled to room temperature, washed with distilled water and extracted with dichloromethane. In 5% NH ₄ Cl aqueous washing the DCM layer was extracted, the dried MgSO _4, filtered, evaporated under reduced pressure to remove the solvent, and filtered through silica gel. The residual solution was concentrated under reduced pressure and purified with EtOAc EtOAc EtOAc

Preparation of Compound C-97

Compound 9-2 (6 g, 23.3 mmol) was dissolved in DMF (60 mL) After that, NaH (1.1 g, 28.0 mmol) was added at 0 ° C and stirred for 10 min. Compound 2-1 (8.8 g, 25.7 mmol) was added to the reaction mixture and stirred for 19 h. After the reaction was terminated, MeOH was added to the reaction mixture. The obtained solid was filtered through EtOAc (EtOAc) (EtOAc)

MS/FAB measured value 656; calculated value 655.81

Example 10: Preparation of Compound C-99

Preparation of Compound 10-1

Compound 3-2 (30 g, 109.7 mmol), 4-bromoiodobenzene (62 g, 219.4 mmol), CuI (20.9 g, 109.7 mmol), ethylenediamine (14.7 mL, 219.4 m) After the molar, K ₃ PO ₄ (58 g, 274.3 mmol) and toluene (600 mL), the reaction mixture was stirred under reflux. After 15 hours, the reaction mixture was cooled to room temperature, filtered and removed under reduced pressure by CuI and K ₃ PO _4. The residual solution was washed with distilled water and extracted with MC. The obtained organic layer was dried (MgSO ₄ ), filtered, evaporated, evaporated,

Preparation of Compound 10-2

Compound 10-1 (25 g, 58.36 mmol) was dissolved in THF (500 mL), and a solution of 2.5 M n-butyllithium in hexane (23.3 mL, 58.36 mmol) was added at -78 °C to the reaction. After the mixture, the reaction mixture was stirred. After 1 hour, B(O i -Pr) ₃ (20.1 mL, 87.54 mmol) was slowly added, and the mixture was stirred for 1 hour. The reaction mixture was stirred at room temperature for 4 hours with a slow increase in temperature. After stirring, distilled water was added, and the reaction mixture was extracted with EA. The obtained organic layer was dried over anhydrous MgSO ₄ to remove residual water, distilled under reduced pressure to remove solvent, and recrystallized from EA and hexane to give compound 10-2 (19 g, 82.78%).

Preparation of Compound C-99

Compound 2-1 (6.1 g, 17.79 mmol), compound 10-2 (7 g, 17.79 mmol), Pd(PPh ₃ ) ₄ (1.0 g, 0.88 mmol), 2MK ₃ PO ₄ After (22 ml), toluene (130 ml) and ethanol (66 ml), the reaction mixture was stirred under reflux. After 4 hours, methanol was added to the reaction mixture. The solid obtained was filtered under reduced pressure, and the filtered solid was filtered to afford compound C-99 (4.0 g, 34.28%).

MS/FAB measured value 656; calculated value 655.81

Example 11: Preparation of Compound C-41

Preparation of Compound 11-1

Mixing (1,1'-biphenyl)-3-ylboronic acid (25 g, 0.1 mol), 1-bromo-4-iodobenzene (89.3 g, 0.32 mol), Pd(PPh ₃ ) ₂ Cl ₂ ( After 2.7 g, 0.038 mol, Na ₂ CO ₃ (26 g, 0.25 mol), toluene (150 ml), EtOH (38 ml) and distilled water (150 ml), the reaction mixture was stirred at 110 ° C for 3 hours. After the reaction was terminated, the reaction mixture was extracted with EA. The obtained organic layer was dried over anhydrous MgSO ₄ to remove residual water, distilled under reduced pressure to remove solvent, and filtered through a column to give compound 11-1 (31 g, 80%).

Preparation of Compound 11-2

Compound 11-1 (31 g, 0.1 mol) was dissolved in THF (750 mL), and a solution of 2.25 M hexanes hexane (60 ml) was added to the reaction mixture at -78 ° C, and then the reaction was stirred. mixture. After 1 hour, added slowly _{B (O i --Pr) 3 (} 46 mL, 0.2 mole), and the reaction mixture was stirred for 12 hours at room temperature, with gentle warming. After stirring, distilled water was added, and the reaction mixture was extracted with EA. The obtained organic layer was dried over anhydrous MgSO ₄ to remove residual water, distilled under reduced pressure to remove solvent, and filtered through a column to give compound 11-2 (21 g, 76%).

Preparation of Compound 11-3

Mix 2,4-dichloropyrimidine (7.6 g, 0.05 mol), compound 11-2 (10.7 g, 0.39 mol), Pd(PPh ₃ ) ₄ (2.3 g, 0.02 mol), Na ₂ CO ₃ ( After 10 g, 0.089 mol, toluene (200 ml), EtOH (50 ml) and purified water (50 ml), the reaction mixture was stirred at 120 ° C for 12 hours. After the reaction was terminated, the reaction mixture was extracted with EA. The obtained organic layer was dried over anhydrous MgSO ₄ to remove residual water, distilled under reduced pressure to remove solvent, and recrystallized to give compound 11-3 (9.4 g, 70%).

Preparation of Compound C-41

After dissolving 60% NaH (1.0 g, 0.025 mol) in DMF (40 ml), the solution was stirred. After dissolving Compound 1-2 (5.0 g, 0.017 mol) in DMF (40 mL), this solution was added to a NaH solution and stirred for 1 hour. Compound 11-3 (7.2 g, 0.017 mol) was dissolved in DMF (20 ml), and after stirring, a mixed solution of compound 1-2 was added to a mixed solution of compound 11-3, and stirred for 12 hours. The resulting yellow solid was filtered, washed with MeOH and crystallised to afford compound C-41 (5 g, 48%).

MS/FAB measured value 590; calculated value 589.73

Test Example 1: Preparation of an OLED device using the compound of the present invention

An OLED device is prepared using the compounds of the invention. A transparent electrode indium tin oxide (ITO) film for use on a glass substrate of an organic light-emitting diode (OLED) device (Samsung Corning, Republic of Korea) was washed with a mixture of trichloroethylene, acetone, ethanol, and distilled water using ultrasonic waves ( 15 Ω/sq) and then stored in isopropanol. Thereafter, the ITO substrate was mounted on a substrate holder of a vacuum vapor deposition apparatus. N ¹ ,N ^{1 '} -([1,1'-biphenyl]-4,4'-diyl) bis(N ¹ -(naphthalen-1-yl)-N ⁴ ,N ⁴ -diphenylbenzene -1,4-Diamine) is introduced into the cell of the vacuum vapor deposition apparatus, and then the chamber pressure of the apparatus is controlled to 10 ^-6 torr. Thereafter, a current was applied to the cell to evaporate the material introduced, thereby forming a hole injecting layer having a thickness of 60 nm on the ITO substrate. Thereafter, N,N'-bis(4-biphenyl)-N,N'-bis(4-biphenyl)-4,4'-diaminobiphenyl is introduced into the vacuum vapor deposition apparatus. A cell, and by applying a current to the cell to evaporate, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer. Thereafter, the compound C-67 was introduced into one chamber of the vacuum vapor deposition apparatus as a host material, and the compound D-56 was introduced into another chamber as a dopant. The two materials were evaporated at different rates and deposited at a doping amount of 15% by weight (wt%) to form a light-emitting layer having a thickness of 30 nm on the hole transport layer. Thereafter, 2-(4-(9,10-di(naphthalen-2-yl)indol-2-yl)phenyl)-1-phenyl-1H-benzo[ d ]imidazole is introduced into a chamber and 8 Lithium quinolate is introduced into another chamber. The two materials were evaporated at the same rate and deposited at a doping amount of 50% by weight to form an electron transport layer having a thickness of 30 nm on the light-emitting layer. Thereafter, after depositing lithium hydroxyquinolate having a thickness of 2 nm as an electron injecting layer on the electron transporting layer, an Al cathode having a thickness of 150 nm was deposited on the electron injecting layer by another vacuum vapor deposition apparatus. Thus an OLED device is produced. All materials used to make the OLED device were purified by vacuum sublimation of 10 ^-6 torr prior to use.

The obtained OLED device showed green light emission having a luminance of 1,040 cd/m ² and a current density of 2.29 mA/cm ² at a driving voltage of 3.0 V.

Test Example 2: Preparation of an OLED device using the compound of the present invention

An OLED device was prepared in the same manner as in Example 1, except that the compound C-41 was used as a host material, and the compound D-5 was used as a dopant.

The obtained OLED device showed green light emission having a luminance of 1,030 cd/m ² and a current density of 2.60 mA/cm ² at a driving voltage of 3.2 V.

Test Example 3: Preparation of an OLED device using the compound of the present invention

An OLED device was prepared in the same manner as in Example 1, except that the compound C-55 was used as a host material, and the compound D-57 was used as a dopant.

The obtained OLED device showed green light emission having a luminance of 1,050 cd/m ² and a current density of 2.35 mA/cm ² at a driving voltage of 3.9 V.

Test Example 4: Preparation of an OLED device using the compound of the present invention

An OLED device was prepared in the same manner as in Example 1, except that Compound C-56 was used as a host material, and Compound D-57 was used as a dopant.

The obtained OLED device showed green light emission having a luminance of 1,040 cd/m ² and a current density of 2.09 mA/cm ² at a driving voltage of 4.0 V.

Test Example 5: Preparation of an OLED device using the compound of the present invention

An OLED device was prepared in the same manner as in Example 1, except that Compound C-56 was used as a host material, and Compound D-58 was used as a dopant.

The obtained OLED device showed orange light emission having a luminance of 1,060 cd/m ² and a current density of 2.67 mA/cm ² at a driving voltage of 3.0 V.

Test Example 6: Preparation of an OLED device using the compound of the present invention

An OLED device was prepared in the same manner as in Example 1, except that Compound C-71 was used as a host material, and compound D-34 was used as a dopant.

The obtained OLED device showed green light emission having a luminance of 1,020 cd/m ² and a current density of 2.51 mA/cm ² at a driving voltage of 3.8 V.

Test Example 7: Preparation of an OLED device using the compound of the present invention

An OLED device was prepared in the same manner as in Example 1, except that Compound C-73 was used as a host material, and Compound D-34 was used as a dopant.

The obtained OLED device showed green light emission having a luminance of 1,000 cd/m ² and a current density of 2.17 mA/cm ² at a driving voltage of 3.3 V.

Test Example 8: Preparation of an OLED device using the compound of the present invention

An OLED device was prepared in the same manner as in Example 1, except that the compound C-87 was used as a host material, and the compound D-5 was used as a dopant.

The obtained OLED device showed green light emission having a luminance of 1,030 cd/m ² and a current density of 2.52 mA/cm ² at a driving voltage of 3.5 V.

Test Example 9: Preparation of an OLED device using the compound of the present invention

An OLED device was prepared in the same manner as in Example 1, except that the compound C-87 was used as a host material, and the compound D-59 was used as a dopant.

The obtained OLED device showed a deep orange light emission having a luminance of 1,040 cd/m ² and a current density of 6.34 mA/cm ² at a driving voltage of 3.2 V.

Test Example 10: Preparation of an OLED device using the compound of the present invention

An OLED device was prepared in the same manner as in Example 1, except that the compound C-90 was used as a host material, and the compound D-5 was used as a dopant.

The obtained OLED device showed green light emission having a luminance of 1,050 cd/m ² and a current density of 2.45 mA/cm ² at a driving voltage of 3.1 V.

Test Example 11: Preparation of an OLED device using the compound of the present invention

An OLED device was prepared in the same manner as in Example 1, except that the compound C-91 was used as a host material, and the compound D-5 was used as a dopant.

The obtained OLED device showed green light emission having a luminance of 1,050 cd/m ² and a current density of 2.18 mA/cm ² at a driving voltage of 3.7 V.

Test Example 12: Preparation of an OLED device using the compound of the present invention

An OLED device was prepared in the same manner as in Example 1, except that the compound C-94 was used as a host material, and the compound D-37 was used as a dopant.

The obtained OLED device showed green light emission having a luminance of 1,020 cd/m ² and a current density of 3.15 mA/cm ² at a driving voltage of 4.3 V.

Test Example 13: Preparation of an OLED device using the compound of the present invention

An OLED device was prepared in the same manner as in Example 1, except that the compound C-97 was used as a host material, and the compound D-34 was used as a dopant.

The obtained OLED device showed green light emission having a luminance of 1,070 cd/m ² and a current density of 2.30 mA/cm ² at a driving voltage of 4.1 V.

Test Example 14: Preparation of an OLED device using the compound of the present invention

An OLED device was prepared in the same manner as in Example 1, except that the compound C-98 was used as a host material, and the compound D-5 was used as a dopant.

The obtained OLED device showed green light emission having a luminance of 1,050 cd/m ² and a current density of 2.39 mA/cm ² at a driving voltage of 3.1 V.

Test Example 15: Preparation of an OLED device using the compound of the present invention

An OLED device was prepared in the same manner as in Example 1, except that the compound C-99 was used as a host material, and the compound D-5 was used as a dopant.

The obtained OLED device showed green light emission having a luminance of 1,040 cd/m ² and a current density of 2.66 mA/cm ² at a driving voltage of 3.2 V.

Comparative Example 1: Preparation of an OLED device using a conventional electroluminescent compound

An OLED device was prepared in the same manner as in Example 1, except that 4,4'-bis(carbazol-9-yl)biphenyl (CBP) was used as a host material and Compound D-5 was used as a dopant to introduce the vacuum gas. A cavity barrier layer having a thickness of 10 nm was deposited in a chamber of a phase deposition apparatus and by using bis(2-methyl-8-hydroxyquinoline) (p-phenylphenol) aluminum (III) (Balq).

The obtained OLED device showed green light emission having a luminance of 1,000 cd/m ² and a current density of 2.86 mA/cm ² at a driving voltage of 4.9 V.

Comparative Example 2: Preparation of an OLED device using a conventional electroluminescent compound

An OLED device was prepared in the same manner as in Example 1, except that 4,4'-bis(carbazol-9-yl)biphenyl (CBP) was used as a host material and Compound D-58 was used as a dopant to introduce the vacuum gas. A cavity barrier layer having a thickness of 10 nm was deposited in a chamber of a phase deposition apparatus and by using bis(2-methyl-8-hydroxyquinoline) (p-phenylphenol) aluminum (III) (Balq).

The obtained OLED device showed orange light emission having a luminance of 1,000 cd/m ² and a current density of 3.05 mA/cm ² at a driving voltage of 4.6 V.

The compounds of the present invention have superior luminescent properties compared to conventional materials. Further, the apparatus using the compound of the present invention as a host material for green light or orange light emission not only has superior light-emitting characteristics, but also causes increased power efficiency by reducing the driving voltage.

Claims (6)

a compound represented by the formula (1), Wherein L ₁ represents a single bond, a substituted or unsubstituted 3 to 30 membered heteroaryl group, a substituted or unsubstituted (C6-C30) extended aryl group, or a substituted or unsubstituted group (C3) -C30)cycloalkyl group; X ₁ and X ₂ each independently represent CH or N; Y ₁ and Y ₂ each independently represent -O-, -S-, -CR ₅ R ₆ - or -NR ₇ -, restrictions Y ₁ and Y _{2 are} not present at the same time; Ar ₁ and Ar ₂ each independently represent hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) An aryl group, or a substituted or unsubstituted 3 to 30 membered heteroaryl; each of R ₁ to R ₄ independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, Substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted 3 to 30 membered heteroaryl, substituted or unsubstituted (C3-C30)cycloalkyl, substituted or unsubstituted Substituted 5 to 7 membered heterocycloalkyl, substituted or unsubstituted (C6-C30) aryl (C1-C30) alkyl, -NR ₁₁ R ₁₂ , -SiR ₁₃ R ₁₄ R ₁₅ , -SR ₁₆ , -OR _17, cyano, nitro, or hydroxy; or the R ₁ to R ₄ bonded to the one or more adjacent substituents to form a monocyclic or The (C5-C30) aliphatic or aromatic ring, and one of the ring carbon atoms or more may be at least one heteroatom selected from nitrogen, oxygen and sulfur of substituted; R ₅ to R ₇ and R ₁₁ to R ₁₇ each Independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted 3 to 30 member Aryl, substituted or unsubstituted 5 to 7 membered heterocycloalkyl, or substituted or unsubstituted (C3-C30)cycloalkyl; or R ₅ to R ₇ and R ₁₁ to R ₁₇ Bonding to one or more adjacent substituents to form a monocyclic or polycyclic (C5-C30) alicyclic or aromatic ring, and one or more carbon atoms of the ring may be selected from at least one selected from the group consisting of nitrogen and oxygen And a hetero atom substitution of sulfur; a, b, c and d each independently represent an integer from 1 to 4; wherein when a, b, c or d is an integer of 2 or more, each R ₁ , each R ₂ Each R ₃ or each R ₄ is the same or different; the heterocycloalkyl group and the (hetero)heteroaryl group contain at least one member selected from the group consisting of B, N, O, S, P(=O), Si, and P hetero atom. The compound of claim 1, wherein the substituted alkyl group, substituted (stretched) of the groups L ₁ , Ar ₁ , Ar ₂ , R ₁ to R ₇ and R ₁₁ to R ₁₇ The substituents of the aryl group, the substituted (extended) heteroaryl group, the substituted (extended) cycloalkyl group, the substituted heterocycloalkyl group and the substituted aralkyl group are each independently selected from the group consisting of At least one of: hydrazine, halogen, halogen-substituted or unsubstituted (C1-C30) alkyl, (C6-C30) aryl, substituted by (C1-C30)alkyl or (C6-C30) aryl or Unsubstituted 3 to 30 membered heteroaryl, (C3-C30)cycloalkyl, 5 to 7 membered heterocycloalkyl, tris(C1-C30)alkyldecane, tris(C6-C30)aryldecane , bis(C1-C30)alkyl (C6-C30) arylalkyl, (C1-C30)alkylbis(C6-C30)aryldecyl, (C2-C30)alkenyl, (C2-C30 Alkynyl, cyano, N-carbazolyl, bis(C1-C30)alkylamino, bis(C6-C30)arylamino, (C1-C30)alkyl(C6-C30)arylamine Base, di(C6-C30) aryl boroncarbonyl, di(C1-C30)alkyl boroncarbonyl, (C1-C30)alkyl (C6-C30) aryl boroncarbonyl, (C6-C30) aryl (C1 -C30)alkyl, (C1-C30)alkyl (C6-C30) aryl, carboxyl, And hydroxy groups. The compound according to claim 1, wherein the formula (1) The part is selected from the following structures: Wherein, R ₅ , R ₆ and R _{7 are} as defined in the first item of the patent application. The compound of claim 1, wherein L ₁ represents a single bond, a 3 to 30 member heteroaryl group or a (C6-C30) extended aryl group; and X ₁ and X ₂ each independently represent CH or N; Y ₁ and Y ₂ each independently represent -O-, -S-, -CR ₅ R ₆ - or -NR ₇ -, and the restriction conditions are that Y ₁ and Y _{2 are} not present at the same time; Ar ₁ and Ar ₂ each independently represent hydrogen, Anthracene, halogen, (C1-C30)alkyl, (C6-C30)aryl, or 3 to 30 membered heteroaryl; R ₁ to R ₄ each independently represent hydrogen, deuterium, halogen, (C1-C30)alkyl , (C6-C30) aryl, 3 to 30 membered heteroaryl, carbazolyl, or -SiR ₁₃ R ₁₄ R ₁₅ ; R ₅ to R ₇ each independently represent (C1-C30)alkyl, (C6-C30 An aryl group, or a 3 to 30 membered heteroaryl group; or R ₅ and R ₆ groups bonded to each other to form a monocyclic or polycyclic (C5-C30) alicyclic or aromatic ring, and one or more of the rings The carbon atom may be substituted with at least one hetero atom selected from the group consisting of nitrogen, oxygen and sulfur; R ₁₃ to R ₁₅ each independently represent a (C1-C30) alkyl group, a (C6-C30) aryl group, or a 3 to 30 membered heteroaryl group. And the alkyl group and the heteroaryl group of L ₁ , the alkyl group, the aryl group, the heteroaryl group and the oxazolyl group of Ar ₁ and Ar ₂ , and R ₁ to R ₇ and R ₁₃ to R ₁₅ Alkyl, aryl and heteroaryl It may be substituted by at least one group selected from the group consisting of hydrazine, halogen, halogen-substituted or unsubstituted (C1-C30) alkyl, (C6-C30) aryl, (C1-C30) alkyl Or (C6-C30) aryl substituted or unsubstituted 3 to 30 membered heteroaryl, (C3-C30)cycloalkyl, tri(C1-C30)alkyldecyl, tris(C6-C30)aryl矽alkyl, bis(C1-C30)alkyl(C6-C30)aryldecyl, (C1-C30)alkylbis(C6-C30)aryldecyl, oxazolyl, bis(C1-C30)alkane Amino group, bis(C6-C30)arylamino group, (C1-C30)alkyl (C6-C30) arylamino group, (C6-C30) aryl (C1-C30) alkyl group, and (C1 -C30) alkyl (C6-C30) aryl. The compound according to claim 1, wherein the compound represented by the formula (1) is selected from the group consisting of: An organic electric field illuminating device comprising the compound according to claim 1 of the patent application.