KR20160035562A - Novel benzophenanthrene derivatives typed compound and the organic electroluminescence display device using same - Google Patents

Novel benzophenanthrene derivatives typed compound and the organic electroluminescence display device using same Download PDF

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KR20160035562A
KR20160035562A KR1020150134107A KR20150134107A KR20160035562A KR 20160035562 A KR20160035562 A KR 20160035562A KR 1020150134107 A KR1020150134107 A KR 1020150134107A KR 20150134107 A KR20150134107 A KR 20150134107A KR 20160035562 A KR20160035562 A KR 20160035562A
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김근태
김봉기
김성훈
안현철
함호완
김동준
이형진
임동환
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주식회사 동진쎄미켐
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Abstract

The present invention relates to a novel benzophenanthrene derivative compound and an organic light emitting device comprising the same and, more specifically, to a benzophenanthrene derivative compound and an organic light emitting device using the same, wherein the benzophenanthrene derivative compound has low driving voltage and high light emitting efficiency, and implements low electric power consumption by preventing energy loss. The compound is represented by any one of chemical formulas 1 to 4.

Description

TECHNICAL FIELD [0001] The present invention relates to novel benzophenanthrene derivative compounds, and organic electroluminescent devices using the same.

The present invention relates to a novel benzophenanthrene derivative compound and an organic light emitting device using the same. More particularly, the present invention relates to a benzophenanthrene derivative compound capable of realizing low power consumption by preventing low driving voltage, high luminous efficiency and energy loss, To an organic light emitting device using the same.

Recently, an organic light emitting device capable of being driven by a low voltage in a self-emission type has a better viewing angle and contrast ratio than a liquid crystal display (LCD), which is a mainstream of a flat panel display device, and is lightweight and thin, The display device has attracted attention as a next-generation display device.

Generally, an organic light emitting device has a structure including a cathode (electron injection electrode), a cathode (hole injection electrode), and an organic layer between the two electrodes. In this case, the organic layer may include a hole injection layer (HIL), a hole transport layer (HTL), an electron transport layer (ETL), or an electron injection layer (EIL) electron injection layer, and may further include an electron blocking layer (EBL) or a hole blocking layer (HBL) on the emission characteristics of the light emitting layer.

When an electric field is applied to the organic light emitting device having such a structure, holes are injected from the anode, electrons are injected from the cathode, and holes and electrons recombine in the light emitting layer through the hole transporting layer and the electron transporting layer to form luminescent excitons do. The formed luminescent excitons emit light while transitioning to ground states. A luminescent dye (dopant) is also doped in the light emitting layer (host) in order to increase the efficiency and stability of the light emitting state.

Various compounds have been known as materials used in the light emitting layer of organic light emitting devices. However, organic light emitting devices using known light emitting materials have been difficult to put to practical use due to high driving voltage, low efficiency, and short life span. Accordingly, efforts have been made to develop organic light emitting devices having low voltage driving, high efficiency, and long lifetime by using materials having excellent light emission characteristics.

In order to solve the problems of the prior art as described above, the present invention provides a process for producing a benzophenanthrene derivative compound and a benzophenanthrene derivative compound capable of realizing low power consumption by preventing low driving voltage, high luminous efficiency and energy loss of an organic light emitting device And an organic electroluminescent device.

In order to achieve the above object, the present invention provides a benzophenanthrene derivative compound represented by any one of the following Chemical Formulas 1 to 4:

[Chemical Formula 1]

Figure pat00001

(2)

Figure pat00002

(3)

Figure pat00003

[Chemical Formula 4]

Figure pat00004

In the above Chemical Formulas 1 to 4,

R 1 to R 16 each independently represent a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C3-C20 heterocycloalkyl group, a substituted or unsubstituted C6- A substituted or unsubstituted C1-C40 aryl group, a substituted or unsubstituted C3-C40 hetero aryl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, A substituted or unsubstituted C1-C30 alkylamino group, a substituted or unsubstituted C3-C20 cycloalkylamino group, a substituted or unsubstituted C3-C20 heterocycloalkylamino group, a substituted or unsubstituted C6-C30 arylamino group, a substituted or unsubstituted C6- A substituted or unsubstituted aralkylamino group having 6 to 30 carbon atoms, a substituted Represents a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, A halogen group, deuterium, and hydrogen.

The present invention also provides an organic light emitting device comprising the benzophenanthrene derivative compound.

The novel benzophenanthrene derivative compound according to the present invention can exhibit a low driving voltage and a high luminous efficiency. In particular, the novel benzophenanthrene derivative compound of the present invention has a distinctive structure of naphthalene and phenyl Since cyclization is performed on the ethyl group or the methyl group, it is possible to reduce the delamination due to the pi bonding and prevent the energy loss due to the rotation. Thus, the energy loss can be prevented and low power consumption can be realized.

1 is a schematic view illustrating the structure of an organic light emitting diode according to an embodiment of the present invention.

Hereinafter, the present invention will be described in detail.

The present invention provides a benzophenanthrene derivative compound represented by any one of the following formulas (1) to (4):

[Chemical Formula 1]

Figure pat00005

(2)

Figure pat00006

(3)

Figure pat00007

[Chemical Formula 4]

Figure pat00008

In the above Chemical Formulas 1 to 4,

R 1 to R 16 each independently represent a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C3-C20 heterocycloalkyl group, a substituted or unsubstituted C6- A substituted or unsubstituted C1-C40 aryl group, a substituted or unsubstituted C3-C40 hetero aryl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, A substituted or unsubstituted C1-C30 alkylamino group, a substituted or unsubstituted C3-C20 cycloalkylamino group, a substituted or unsubstituted C3-C20 heterocycloalkylamino group, a substituted or unsubstituted C6-C30 arylamino group, a substituted or unsubstituted C6- A substituted or unsubstituted aralkylamino group having 6 to 30 carbon atoms, a substituted Represents a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, A halogen group, deuterium, and hydrogen.

Specific examples of the alkyl group as the substituent used in the present invention include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isoamyl group, a hexyl group, a heptyl group, A halogen atom, a hydroxyl group, a nitro group, a cyano group, a trifluoromethyl group, a silyl group (in this case, a " (R '), wherein R, R' and R "are each independently a C 1 to C 6 alkyl group, a substituted or unsubstituted amino group (-NH 2, -NH A hydroxyl group, a phosphoric acid group, an alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, a halogenated alkyl group having 1 to 24 carbon atoms, an alkylamino group having 1 to 24 carbon atoms (in this case, An alkenyl group having 2 to 24 carbon atoms, an alkynyl group having 2 to 24 carbon atoms, By more than 24 heteroaryl group, a heteroarylalkyl group having a carbon number of 5 to 24 aryl group, C 6 -C 24 aryl group, a C 3 -C 24 heteroaryl group, or having from 3 to 24 of which may be substituted.

Specific examples of the alkoxy group used as the substituent in the compound of the present invention include methoxy, ethoxy, propoxy, isobutyloxy, sec-butyloxy, pentyloxy, isoamyloxy, And can be substituted with substituents similar to those in the case of the alkyl group.

Specific examples of the aryl group as the substituent group used in the compound of the present invention include a phenyl group, a 2-methylphenyl group, a 3-methylphenyl group, a 4-methylphenyl group, a 4-ethylphenyl group, Examples of the aryl group include phenyl group, 4-methylbiphenyl group, 4-ethylbiphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, 1-naphthyl group, , Anthryl group, phenanthryl group, pyrenyl group, fluorenyl group, tetrahydronaphthyl group and the like, which may be substituted with the same substituents as those of the alkyl group.

Specific examples of the heteroaryl group used as the substituent in the compound of the present invention include pyridinyl, pyrimidinyl, triazinyl, indolinyl, quinolinyl, pyrrolidinyl, piperidinyl, An oxazolyl group, an oxadiazolyl group, a benzoxazolyl group, a thiazolyl group, a thiadiazolyl group, a benzothiazolyl group, a triazolyl group, an imidazolyl group, a benzoimidazole group, And at least one of the hydrogen atoms of the heteroaryl group may be substituted with the same substituent as the alkyl group.

Specific examples of the alkenyl group used as the substituent in the compound of the present invention include alkenyl groups such as stibenyl group and styrenyl group connected with an aryl group. Specific examples of the cycloalkyl group include a cyclopentyl group and a cyclohexyl group, But is not limited thereto.

The arylamine group, which is a substituent group used in the compound of the present invention, may be selected from the group consisting of a diphenylamine group, a phenylnaphthylamine group, a phenylbiphenylamine group, a naphthylbiphenylamine group, a dinaphthylamine group, a diphenylamine group, a dianthracenylamine Methyl-naphthylamine group, a 2-methyl-biphenylamine group, a 9-methyl-anthracenylamine group, a ditolylamine group, a phenyltolylamine group, Phenylamine group, phenylbiphenylaminophenylamine group, and naphthylphenylaminophenylbiphenylamine group, but the present invention is not limited thereto.

In the present invention, the term "substituted or unsubstituted" refers to a group selected from the group consisting of cyano, halogen, hydroxy, nitro, alkyl, cycloalkyl, heterocycloalkyl, aralkyl, alkoxy, alkylamino, Means substituted or unsubstituted with at least one substituent selected from the group consisting of an aralkyl group, an aralkyl group, an aralkyl group, an aryl group, an aryl group, an aryl group, an aryl group, a heteroaryl group, germanium, phosphorus, boron, hydrogen and deuterium .

Specifically, the benzophenanthrene derivative compound of the present invention is preferably selected from the group represented by the following formula, but is not limited thereto.

Figure pat00009
,
Figure pat00010
,
Figure pat00011
,
Figure pat00012
,
Figure pat00013
,

Figure pat00014
,
Figure pat00015
,
Figure pat00016
,
Figure pat00017
,
Figure pat00018
,
Figure pat00019
,
Figure pat00020
,
Figure pat00021
,
Figure pat00022
,
Figure pat00023
,
Figure pat00024
,
Figure pat00025
,
Figure pat00026
,
Figure pat00027
,
Figure pat00028
,
Figure pat00029
,
Figure pat00030
,

Figure pat00031
,
Figure pat00032
,
Figure pat00033
,
Figure pat00034
.
Figure pat00035
,
Figure pat00036
,
Figure pat00037
,
Figure pat00038
,
Figure pat00039
,
Figure pat00040
,
Figure pat00041
,
Figure pat00042
,
Figure pat00043
,
Figure pat00044
,
Figure pat00045
,
Figure pat00046
,
Figure pat00047
,
Figure pat00048
,
Figure pat00049
,
Figure pat00050
,
Figure pat00051
,

Figure pat00052
,
Figure pat00053
,
Figure pat00054
,
Figure pat00055
,
Figure pat00056
,
Figure pat00057
,
Figure pat00058
,
Figure pat00059
,
Figure pat00060
,
Figure pat00061
,
Figure pat00062
,
Figure pat00063
,
Figure pat00064
,
Figure pat00065
,
Figure pat00066
,
Figure pat00067
,
Figure pat00068
,
Figure pat00069
,
Figure pat00070
,
Figure pat00071
,

Figure pat00072
,
Figure pat00073
,
Figure pat00074
,
Figure pat00075
,
Figure pat00076
,
Figure pat00077
,
Figure pat00078
,
Figure pat00079
,
Figure pat00080
,
Figure pat00081
,
Figure pat00082
,
Figure pat00083
,
Figure pat00084
,
Figure pat00085
,
Figure pat00086
,
Figure pat00087
,
Figure pat00088
,
Figure pat00089
,

Figure pat00090
,
Figure pat00091
,
Figure pat00092
,
Figure pat00093
,
Figure pat00094
,
Figure pat00095
,
Figure pat00096
,
Figure pat00097
,
Figure pat00098
,
Figure pat00099
,
Figure pat00100
,
Figure pat00101
,
Figure pat00102
,
Figure pat00103
,
Figure pat00104
,
Figure pat00105
,
Figure pat00106
,
Figure pat00107
,
Figure pat00108
,
Figure pat00109
,
Figure pat00110
,
Figure pat00111
,
Figure pat00112
,
Figure pat00113
, ,
Figure pat00115
,
Figure pat00116
,
Figure pat00117
,
Figure pat00118
,
Figure pat00119
,
Figure pat00120
,
Figure pat00121
,
Figure pat00122
,
Figure pat00123
,
Figure pat00124
,
Figure pat00125
,
Figure pat00126
,
Figure pat00127
,
Figure pat00128
,
Figure pat00129
,

Figure pat00130
,
Figure pat00131
,
Figure pat00132
,
Figure pat00133
,
Figure pat00134
,
Figure pat00135
,
Figure pat00136
,
Figure pat00137
,
Figure pat00138
,
Figure pat00139
,
Figure pat00140
,
Figure pat00141
,
Figure pat00142
,
Figure pat00143
,
Figure pat00144
,
Figure pat00145
,
Figure pat00146
,
Figure pat00147
,
Figure pat00148
,
Figure pat00149
,
Figure pat00150
,
Figure pat00151
,

Figure pat00152
,
Figure pat00153
,
Figure pat00154
,
Figure pat00155
,
Figure pat00156
,
Figure pat00157
,
Figure pat00158
,
Figure pat00159
,
Figure pat00160
,
Figure pat00161
,
Figure pat00162
,
Figure pat00163
,
Figure pat00164
,
Figure pat00165
,
Figure pat00166
,
Figure pat00167
,
Figure pat00168
,
Figure pat00169
,
Figure pat00170
,

Figure pat00171
,
Figure pat00172
,
Figure pat00173
,
Figure pat00174
,
Figure pat00175
,
Figure pat00176
,
Figure pat00177
,
Figure pat00178
,
Figure pat00179
,
Figure pat00180
,
Figure pat00181
,
Figure pat00182
,
Figure pat00183
,
Figure pat00184
,
Figure pat00185
,
Figure pat00186
,
Figure pat00187
,
Figure pat00188
,
Figure pat00189
,
Figure pat00190
,
Figure pat00191
,
Figure pat00192
,
Figure pat00193
,
Figure pat00194
,
Figure pat00195
,
Figure pat00196
,
Figure pat00197
,
Figure pat00198
,
Figure pat00199

In the present invention, the benzophenanthrene derivative compound can be prepared through the following process for producing a base material.

Formula (1)

Figure pat00200

Formula (2)

Figure pat00201

Formula (3)

Figure pat00202

Formula 4

Figure pat00203

In the above schemes 1 to 4, each R is independently hydrogen, halogen, R 1 to R 16 defined in formulas (1) to (4), and specifically at least one of R may be halogen. Each halogen may be independently substituted with a substituent of R 1 to R 16 as shown in formulas (1) to (4). Herein, Suzuki reaction or Ullmann reaction can be applied as a method of introducing a substituent, but the present invention is not limited thereto.

The present invention also provides an organic light emitting device comprising the benzophenanthrene derivative compound.

The organic light emitting device of the present invention may further include at least one layer selected from the group consisting of a light emitting layer, a hole injecting layer, a hole transporting layer, a hole blocking layer, an electron transporting layer, an electron injecting layer and an electron blocking layer between the anode and the cathode, Wherein the phenanthrene derivative compound is contained in at least one of the layers.

In particular, the benzophenanthrene derivative compound according to the present invention is preferably included in the light emitting layer between the anode and the cathode.

In addition, the layer between the anode and the cathode may be formed by a deposition method or a solution process. In the solution process, a thin film layer forming material is prepared as a solution to form a thin film layer, and a thin film layer is formed by using spray coating, tip coating, spin coating, printing or the like, Can be further secured.

Also, the present invention can be used variously such as a display device, a display device, and a monochromatic or white illumination device including the organic light emitting device.

The method of manufacturing the organic light emitting diode according to the present invention will now be described in more detail.

The organic light emitting device according to the present invention includes a hole injecting layer (HIL), a hole transporting layer (HTL), a light emitting layer (EML), an electron transporting layer (ETL), an electron injecting layer (EIL), etc., between an anode and a cathode And may have a structure as shown in FIG. 1, for example.

First, a material for an anode electrode having a high work function is deposited on the substrate to form an anode. At this time, the substrate can be a substrate used in a conventional organic light emitting device, and it is particularly preferable to use an organic substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness. As the material for the anode electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO) and the like which are transparent and excellent in conductivity can be used. The anode electrode material can be deposited by a conventional anode formation method, and specifically, it can be deposited by a deposition method or a sputtering method.

Next, a hole injection layer (HIL) material may be formed on the anode electrode by a method such as a vacuum deposition method, a spin coating method, a casting method, or an LB (Langmuir-Blodgett) method. However, In addition, it is preferable to be formed by a vacuum evaporation method in that pin holes are hardly generated. When the hole injection layer is formed by the vacuum deposition method, the deposition conditions vary depending on the compound used as the material of the hole injection layer, the structure and thermal properties of the desired hole injection layer, and the like. In general, the deposition temperature is 50-500 [ A vacuum degree of 10 -8 -10 -3 Torr, a deposition rate of 0.01-100 A / sec, and a film thickness range of 10-5 탆.

As the hole injection layer material, a known material can be used. For example, a phthalocyanine compound such as copper phthalocyanine disclosed in U.S. Patent No. 4,356,429 or a star burst type amine derivative TCTA (4,4 ', 4 "-tri (N (4,4 ', 4 "-tris (3-methylphenylamino) triphenylamine), m-MTDATA Amino) phenoxybenzene, Advanced Material, 6, p677 (1994)), HI-406 (N1, N1'- (biphenyl-4,4'-diyl) bis (N1- (naphthalen- , N4-diphenylbenzene-1,4-diamine), or the like can be used as the hole injection layer material.

Next, a hole transport layer (HTL) material may be formed on the hole injection layer by a method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method. However, a uniform film quality is easily obtained, It is preferable to be formed by vacuum evaporation. When the hole transport layer is formed by the vacuum deposition method, the deposition conditions vary depending on the compound used, but it is generally preferable to select the conditions within the same range as the formation of the hole injection layer.

The hole transport layer material is not particularly limited, but it is possible to use the compound represented by any one of formulas 1 to 4 according to the present invention, or to use it by arbitrarily selecting from among conventionally known substances used in the hole transport layer. Specifically, the hole transport layer material may contain, in addition to the compounds represented by any one of Chemical Formulas 1 to 4 according to the present invention, a carbazole derivative such as N-phenylcarbazole or polyvinylcarbazole, a N, N'-bis (3-methylphenyl) -N, N'-diphenyl- [1,1-biphenyl] -4,4'-diamine (TPD), N, N'-di (naphthalen- (? -NPD), and the like can be used.

Thereafter, a light emitting layer (EML) material may be formed on the hole transporting layer by a method such as vacuum deposition, spin coating, casting, or LB method. It is preferable to form it by a vacuum evaporation method. When the light emitting layer is formed by the vacuum vapor deposition method, the deposition conditions vary depending on the compound used, but it is generally preferable to select the conditions within the substantially same range as the formation of the hole injection layer. The light emitting layer material may be used alone or as a dopant or a host compound represented by any one of formulas (1) to (4) of the present invention.

When the compound represented by any one of Chemical Formulas 1 to 4 or a mixture of two or more thereof is used as a light emitting host and a dopant, a phosphorescent or fluorescent dopant and a host may be used together to form a light emitting layer. As the fluorescent dopant, IDE102 or IDE105 or BD142 available from Idemitsu can be used. As the phosphorescent dopant, green phosphorescent dopant Ir (ppy) 3 (fac-tris (2-phenylpyridine) iridium) The blue phosphorescent dopant FIrpic (iridium (III) bis [(4,6-di-fluorophenyl) -pyridinato-N, C2 '] picolinate) and UDC's red phosphorescent dopant RD61 can be commonly vacuum deposited (doped). The doping concentration of the dopant is not particularly limited, but the concentration of the dopant is preferably 0.01 to 15 parts by weight relative to 100 parts by weight of the host.

When the phosphorescent dopant is used together with the phosphorescent dopant, it is preferable to further laminate the hole blocking material (HBL) by a vacuum evaporation method or a spin coating method in order to prevent the triplet exciton or the hole from diffusing into the electron transporting layer (HTL) Do. The hole blocking material which can be used at this time is not particularly limited, but any known hole blocking material may be selected and used. Examples thereof include oxadiazole derivatives and triazole derivatives, phenanthroline derivatives, and hole blocking materials described in Japanese Patent Laid-open Publication No. 11-329734 (A1). Representative examples include Balq, phenanthrolines ) Based compound (for example, UDC BCP) may be used.

An electron transport layer (ETL) material is formed on the light emitting layer formed as described above. The electron transport layer is formed by a vacuum deposition method, a spin coating method, a casting method, or the like, and is preferably formed by a vacuum deposition method.

The electron transport layer material serves to stably transport electrons injected from an electron injection electrode, and the kind thereof is not particularly limited, and examples thereof include quinoline derivatives, especially tris (8-quinolinolato) aluminum Alq3) can be used. An electron injection layer (EIL), which is a material having a function of facilitating the injection of electrons from the cathode, may be laminated on the electron transport layer. Examples of the electron injection layer material include LiF, NaCl, CsF, Li 2 O, BaO Can be used.

The conditions for the deposition of the electron transport layer (ETL) vary depending on the compound used, but it is generally preferable to select the deposition conditions in substantially the same range as the formation of the hole injection layer.

Then, an electron injection layer (EIL) material may be formed on the electron transport layer, and the electron transport layer may be formed by vacuum evaporation, spin coating, casting, or the like, It is preferably formed by a vacuum deposition method.

Finally, a metal for forming a cathode is formed on the electron injection layer by a vacuum evaporation method, a sputtering method, or the like, and used as a cathode. As the metal for cathode formation, a metal, an alloy, an electrically conductive compound having a low work function, and a mixture thereof can be used. Specific examples thereof include Li, Mg, Al, Al-Li, Ca, Mg-In, Mg-Ag, . Also, a transmissive cathode using ITO or IZO may be used to obtain a front light emitting element.

The organic light emitting device of the present invention can be applied to an organic light emitting device having an anode, a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL), an electron injection layer (EIL) It is possible to have not only a light emitting device but also an organic light emitting device having various structures, and it is also possible to form one layer or two layers of intermediate layers as required.

As described above, the thickness of the organic thin film layer formed according to the present invention can be controlled according to the required degree, preferably 10-1,000 nm, and more preferably 20-150 nm.

Hereinafter, the present invention will be described in more detail with reference to the following examples. However, the scope of the present invention is not limited to the following examples.

Synthetic example  1: Compound (5) Synthesis

Figure pat00204

[Synthesis Example 1-1] Synthesis of Compound (2)

Compound (1) (270 g, 1.85 mol) and triethylamine (514 g, 5.08 mol) were added to a 2000 ml flask under argon or nitrogen atmosphere and stirred at room temperature for 15 minutes. Then, trimethylsilyl chloride (541 g, 5.08 mol) was slowly added thereto and stirred for 40 minutes. Then, sodium iodide (369 g, 2.46 mol) was dissolved in 2200 ml of acetonitrile, slowly added thereto at a temperature not exceeding 40 ° C, and stirred for 2 hours. When the reaction was completed, 3 L of cold distilled water was added and extracted twice with 1 L of pentene. After removing water with anhydrous sodium sulfate, the solvent was removed to obtain a brown oil compound (2) (402 g, 96%).

1H NMR (CDCl3, 400 MHz):? 1.85 (s, 9H),? 3.89-3.94 (m, 2H),? 4.34-4.38 (t, 2H),? 6.79 .69-8. 81 (m, 3H),? 9.0-9.02 (d, 1H).

MS (EI) (m / z) [M < + >] 297

[Synthesis Example 1-2] Synthesis of Compound (3)

Trimethyltartioformate (6.22 g, 23.8 mmol) was dissolved in MC in a 500 ml flask under argon or nitrogen atmosphere and maintained at -70 ° C. 1 M solution of tin tetrachloride (23.8 ml, 23.8 mmol) and compound (2) (5.3 g) were added and the mixture was stirred at -70 ° C for 40 minutes.

After completion of the reaction, 50 ml of cold distilled water was added and extracted three times with 20 ml of MC. After removal of water with anhydrous sodium sulfate, the solvent was removed, and hexane and ethyl acetate were subjected to column purification using a mobile phase to obtain Compound (3) (5.8 g, 96%).

1H NMR (CDCl3, 400 MHz):? 2.05 (s, 1H),? 2.59 (m, 1H),? 3.04 (m, 2H),? 3.13 , 1H),? 7.28-7.40 (m, 10H),? 7.50 (d, 2H),? 7.58 (t, 3H),? 7.90 (d, 1H). MS (EI) (m / z) [M < + >] 331

[Synthesis Example 1-3] Synthesis of Compound (4)

Benzyl magnesium chloride (1 g, 40 mmol) was added to a 500 ml flask under an argon or nitrogen atmosphere, and the temperature was maintained at 0 ° C. Compound (3) (1.5 g, 40 mmol) was slowly added thereto and stirred for 1 hour. The temperature was gradually raised to room temperature. When the reaction was completed, 50 ml of saturated aqueous ammonia was added, and the mixture was extracted three times with 30 ml of ethyl acetate. After removing moisture with anhydrous sodium sulfate, the solvent was removed, dissolved in 100 ml of benzene, 1.5 ml of boron triflylide diethyl etherate was added, and the mixture was refluxed with stirring for 15 minutes. After cooling to room temperature, it was neutralized with sodium bicarbonate and extracted with MC. After removing water with anhydrous sodium sulfate, the solvent was removed, and hexane was subjected to column purification on the mobile phase to obtain Compound (4) (0.78 g, 62%).

1H NMR (CDCl3, 400 MHz):? 3.04 (m, 4H),? 7.28-7.40 (m, 6H),? 7.50 (d, 2H),? 7.90 (d, 1H).

MS (EI) (m / z) [M < + >] 309

[Synthesis Example 1-4] Synthesis of Compound (5)

Figure pat00205

Under argon or nitrogen atmosphere, 250 ml of this compound was charged with 4.2 g of compound (4), 6.8 g of 10-phenylanthracene-9-ylboronic acid, 0.6 g of tetrakis (triphenylphosphine) palladium (0) g was dissolved in 50 ml of 1,4-dioxane and 20 ml of water, and the mixture was heated and stirred under reflux for 24 hours. After the reaction, the solution was cooled to room temperature, and the precipitated crystals were separated by filtration. This was recrystallized from toluene to give 2.7 g (40%) of a white solid (5).

MS (EI) (m / z) [M < + >] 482

Synthetic example  2: Compound (6) Synthesis

Figure pat00206

Synthesis was conducted in the same manner as in Synthesis Example 1-4 except that 10- (1-naphthyl) anthracene-9-ylboronic acid was used instead of 10-phenylanthracene-9-ylboronic acid to obtain white solid compound 6 ) 2.5 g (38%).

MS (EI) (m / z) [M < + >] 532

Synthetic example  3: Compound (7) Synthesis

Figure pat00207

Synthesis was conducted in the same manner as in Synthesis Example 1-4, except that 10- (2-naphthyl) anthracene-9-ylboronic acid was used instead of 10-phenylanthracene-9-ylboronic acid to obtain white solid compound 7 ) 2.2 g (35%).

MS (EI) (m / z) [M < + >] 532

Synthetic example  4: Compound (8) Synthesis

Figure pat00208

Synthesis was conducted in the same manner as in Synthesis Example 1-4, except that 10- (9-phenanthryl) anthracene-9-ylboronic acid was used instead of 10-phenylanthracene-9-ylboronic acid to obtain a white solid compound ) 2.8 g (38%).

MS (EI) (m / z) [M < + >] 582

Synthetic example  5: Compound (9) Synthesis

Figure pat00209

Synthesis was conducted in the same manner as in Synthesis Example 1-4, except that 10-phenylanthracene-9- (4-phenyl) -ylboronic acid was used instead of 10-phenylanthracene-9-ylboronic acid to obtain a white solid compound 9) 2.6 g (33%).

MS (EI) (m / z) [M < + >] 558

Synthetic example  6: Compound (10) Synthesis

Figure pat00210

Synthesis was carried out in the same manner except that 10- (2-naphthyl) anthracene-9- (4-phenyl) -ylboronic acid was used instead of 10-phenylanthracene-9- To give 2.8 g (38%) of a white solid compound (10).

MS (EI) (m / z) [M < + >] 608

Synthetic example  7: Synthesis of Compound (11)

Figure pat00211

Compound (4-2) was synthesized by a method similar to Synthesis Example 1-1, Synthesis Example 1-2, and Synthesis Example 1-3, except that Compound (1-2) was used instead of Compound (1).

Figure pat00212

The procedure of Synthesis Example 1-4 was repeated except that the compound (4-2) was used in place of the compound (4) to obtain 2.6 g (39%) of a white solid compound (11).

MS (EI) (m / z) [M < + >] 482

Synthetic example  8: Compound (12) Synthesis

Synthesis was carried out in the same manner as in Synthesis Example 1-1 and Synthesis Example 1-2 using the compound (1-3) instead of the compound (1), and instead of benzyl magnesium chloride, 3-bromobenzyl magnesium chloride was used instead of the compound -3, the compound (4-3) was obtained.

Figure pat00214

3.1 g (41%) of a white solid compound (12) was obtained by a method similar to that of Synthesis Example 1-4, except that the compound (4-3) was used in place of the compound (4).

MS (EI) (m / z) [M < + >] 482

Synthetic example  9: Compound (13) Synthesis

Figure pat00215

In the same manner as in Synthesis Example 8 except for using 4-bromobenzylmagnesium chloride instead of 3-bromobenzylmagnesium chloride, the compound (4-4) was obtained.

Figure pat00216

(40%) of white solid compound (13) was obtained by a method similar to Synthesis Example 1-4 except that the compound (4-4) was used in place of the compound (4).

MS (EI) (m / z) [M < + >] 482

Synthetic example  10: Compound (14) Synthesis

Figure pat00217

Synthesis Example 1-1 and Synthesis Example 1-2 were synthesized in the same manner and synthesized in a similar manner to Synthesis Example 1-3 using 4-bromobenzylmagnesium chloride instead of benzylmagnesium chloride to obtain the compound (4-5) ≪ / RTI >

Figure pat00218

In a 250 ml flask, 10 g of compound (4-5), 10.9 g of 9H-carbazole, 1.1 g of CuI, 24.3 g of tripotassium phosphate, 0.7 g of 1,2-diaminocyclohexane, 100 ml of 4-dioxane was added, and the mixture was stirred for 36 hours while refluxing. After completion of the reaction, the reaction mixture was filtered, and the solvent was removed under reduced pressure. The reaction product was separated by silica gel column chromatography to obtain 3.2 g (22%) of a green solid compound (14).

MS (EI) (m / z) [M < + >] 560

Synthetic example  11: Compound (15) Synthesis

Figure pat00219

Synthesis was carried out in an identical manner to Synthesis Example 10 except that diphenylamine was used in place of 9H-carbazole to obtain 2.7 g (19%) of a light green solid compound (15).

MS (EI) (m / z) [M < + >] 564

[ Example ] Fabrication of organic light emitting device and measurement of physical properties

Organic light emitting devices were fabricated according to a conventional method using the compounds obtained in Synthesis Examples 1 to 11 as light emitting host materials. Comparison was used ADN (9,10-Di (2- naphthyl) anthracene) as the host compound, a light emitting dopant material in BD142 (N 6, N 12 - bis (3,4-dimethylphenyl) -N 6, N 12 - Diimethylylclycine-6,12-diamine) was used.

Specifically, a 650 Å thick hole injection layer (hole injection layer material: HI-406 (N 1 , N 1 ' - (biphenyl-4,4'-diyl ) bis (N 1 - (naphthalen-1-yl) -N 4, N 4 - diphenyl-benzene-1,4-diamine)), a 200 Å thick hole transport layer (hole transport material: bis (N- (1- naphthyl -n- phenyl)) benzidine (α-NPB)), 350 Å thickness of the light emitting layer is doped with BD142 (BD142: N 6, N 12 - bis (3,4-dimethylphenyl) -N 6, N 12 - Diamine), an electron transport layer (electron transport layer material: ET4 (6,6 '- (3,4-dimemethyl-1,1-dimethyl-1H-silanol- , 5-diyl) di-2,2'-bipyridine)) and an aluminum / LiF cathode having a thickness of 1000/10 Å were sequentially deposited to prepare an organic light emitting device.

The luminescent characteristics of the organic light emitting device were measured and are shown in Table 1 below.

Classification Host Voltage
(V) Current efficiency
(cd / A) Luminance
(cd / m < 2 & CIEx CIEy Example 1 Synthesis Example 1 5.54 8.50 887 0.135 0.175 Example 2 Synthesis Example 2 5.45 9.11 922 0.146 0.177 Example 3 Synthesis Example 3 5.41 9.45 943 0.139 0.178 Example 4 Synthesis Example 4 5.52 8.78 902 0.140 0.173 Example 5 Synthesis Example 5 5.63 9.22 911 0.140 0.169 Example 6 Synthesis Example 6 5.52 9.13 867 0.146 0.168 Example 7 Synthesis Example 7 5.59 8.54 881 0.141 0.167 Example 8 Synthesis Example 8 5.68 8.28 852 0.140 0.160 Example 9 Synthesis Example 9 5.70 7.95 873 0.143 0.172 Comparative Example ADN 5.75 6.30 630 0.141 0.169

As shown in Table 1, in Examples 1 to 9, the driving voltage was similar to that of Comparative Example, but the current efficiency and luminance were improved by 1.5 times, and the color coordinates were also excellent.

In addition, the compounds obtained in Synthesis Examples 10 and 11 were used as luminescent dopants in the light emitting layer, BD142 was used as a comparative dopant material, and ADN was used as a host in the light emitting layer. The luminescent characteristics of the organic light emitting device were measured and are shown in Table 2 below.

Classification Dopant Voltage
(V) Current efficiency
(cd / A) Luminance
(cd / m < 2 & CIEx CIEy Example 10 Synthesis Example 10 4.55 5.94 594 0.139 0.122 Example 11 Synthesis Example 11 4.64 5.41 541 0.143 0.111 Comparative Example BD142 5.75 6.30 630 0.141 0.169

As shown in Table 2, Examples 10 and 11 show that the driving voltage is superior to that of Comparative Example. The current efficiency and luminance show similar or low characteristics, but this is a result of movement to the short wavelength region, as can be seen from the CIEy values of the chromaticity coordinates.

As shown in Tables 1 and 2, the novel benzophenanthrene compound of the present invention can be used to produce an organic light emitting device having excellent characteristics such as a driving voltage, a luminous efficiency and a color coordinate.

Claims (7)

A compound represented by any one of the following formulas (1) to (4):
[Chemical Formula 1]
Figure pat00220

(2)
Figure pat00221

(3)
Figure pat00222

[Chemical Formula 4]
Figure pat00223

In the above Chemical Formulas 1 to 4,
R 1 to R 16 each independently represent a substituted or unsubstituted C1-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, a substituted or unsubstituted C3-C20 heterocycloalkyl group, a substituted or unsubstituted C6- A substituted or unsubstituted C1-C40 aryl group, a substituted or unsubstituted C3-C40 hetero aryl group, a substituted or unsubstituted C1-C30 alkoxy group, a substituted or unsubstituted C6-C30 aryloxy group, A substituted or unsubstituted C1-C30 alkylamino group, a substituted or unsubstituted C3-C20 cycloalkylamino group, a substituted or unsubstituted C3-C20 heterocycloalkylamino group, a substituted or unsubstituted C6-C30 arylamino group, a substituted or unsubstituted C6- A substituted or unsubstituted aralkylamino group having 6 to 30 carbon atoms, a substituted Represents a substituted or unsubstituted alkylsilyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, A halogen group, deuterium, and hydrogen. The method according to claim 1,
Wherein said compound is one of the compounds represented by the formula:
Figure pat00224
,
Figure pat00225
,
Figure pat00226
,
Figure pat00227
,
Figure pat00228
,
Figure pat00229
,
Figure pat00230
,
Figure pat00231
,
Figure pat00232
,
Figure pat00233
,
Figure pat00234
,
Figure pat00235
,
Figure pat00236
,
Figure pat00237
,
Figure pat00238
,
Figure pat00239
,
Figure pat00240
,
Figure pat00241
,
Figure pat00242
,
Figure pat00243
,
Figure pat00244
,
Figure pat00245
,
Figure pat00246
,
Figure pat00247
,
Figure pat00248
,
Figure pat00249
.
Figure pat00250
,
Figure pat00251
,
Figure pat00252
,
Figure pat00253
,
Figure pat00254
,
Figure pat00255
,
Figure pat00256
,
Figure pat00257
,
Figure pat00258
,
Figure pat00259
,
Figure pat00260
,
Figure pat00261
,
Figure pat00262
,
Figure pat00263
,
Figure pat00264
,
Figure pat00265
,
Figure pat00266
,
Figure pat00267
,
Figure pat00268
,
Figure pat00269
,
Figure pat00270
,
Figure pat00271
,
Figure pat00272
,
Figure pat00273
,
Figure pat00274
,
Figure pat00275
,
Figure pat00276
,
Figure pat00277
,
Figure pat00278
,
Figure pat00279
,
Figure pat00280
,
Figure pat00281
,
Figure pat00282
,
Figure pat00283
,
Figure pat00284
,
Figure pat00285
,
Figure pat00286
,
Figure pat00287
,
Figure pat00288
,
Figure pat00289
,
Figure pat00290
,
Figure pat00291
,
Figure pat00292
,
Figure pat00293
,
Figure pat00294
,
Figure pat00295
,
Figure pat00296
,
Figure pat00297
,
Figure pat00298
,
Figure pat00299
,
Figure pat00300
,
Figure pat00301
,
Figure pat00302
,
Figure pat00303
,
Figure pat00304
,
Figure pat00305
,
Figure pat00306
,
Figure pat00307
,
Figure pat00308
,
Figure pat00309
,
Figure pat00310
,
Figure pat00311
,
Figure pat00312
,
Figure pat00313
,
Figure pat00314
,
Figure pat00315
,
Figure pat00316
,
Figure pat00317
,
Figure pat00318
,
Figure pat00319
,
Figure pat00320
,
Figure pat00321
,
Figure pat00322
,
Figure pat00323
,
Figure pat00324
,
Figure pat00325
,
Figure pat00326
,
Figure pat00327
,
Figure pat00328
,
Figure pat00329
,
Figure pat00330
,
Figure pat00331
,
Figure pat00332
,
Figure pat00333
,
Figure pat00334
,
Figure pat00335
,
Figure pat00336
,
Figure pat00337
,
Figure pat00338
,
Figure pat00339
,
Figure pat00340
,
Figure pat00341
,
Figure pat00342
,
Figure pat00343
,
Figure pat00344
,
Figure pat00345
,
Figure pat00346
,
Figure pat00347
,
Figure pat00348
,
Figure pat00349
,
Figure pat00350
,
Figure pat00351
,
Figure pat00352
,
Figure pat00353
,
Figure pat00354
,
Figure pat00355
,
Figure pat00356
,
Figure pat00357
,
Figure pat00358
,
Figure pat00359
,
Figure pat00360
,
Figure pat00361
,
Figure pat00362
,
Figure pat00363
,
Figure pat00364
,
Figure pat00365
,
Figure pat00366
,
Figure pat00367
,
Figure pat00368
,
Figure pat00369
,
Figure pat00370
,
Figure pat00371
,
Figure pat00372
,
Figure pat00373
,
Figure pat00374
,
Figure pat00375
,
Figure pat00376
,
Figure pat00377
,
Figure pat00378
,
Figure pat00379
,
Figure pat00380
,
Figure pat00381
,
Figure pat00382
,
Figure pat00383
,
Figure pat00384
,
Figure pat00385
,
Figure pat00386
,
Figure pat00387
,
Figure pat00388
,
Figure pat00389
,
Figure pat00390
,
Figure pat00391
,
Figure pat00392
,
Figure pat00393
,
Figure pat00394
,
Figure pat00395
,
Figure pat00396
,
Figure pat00397
,
Figure pat00398
,
Figure pat00399
,
Figure pat00400
,
Figure pat00401
,
Figure pat00402
,
Figure pat00403
,
Figure pat00404
,
Figure pat00405
,
Figure pat00406
,
Figure pat00407
,
Figure pat00408
, An organic electroluminescent device comprising a compound represented by any one of formulas (1) to (4) described in claim 1. The method of claim 3,
An organic light emitting device comprising the compound of claim 1 in a hole injection layer (HIL), a hole transport layer (HTL) or a light emitting layer (EML) between the anode and the cathode.
5. The method of claim 4,
Further comprising at least one layer selected from the group consisting of a light emitting layer, a hole injecting layer, a hole transporting layer, an electron blocking layer, an electron transporting layer, an electron injecting layer and a hole blocking layer between the anode and the cathode.
6. The method of claim 5,
Wherein at least one layer selected from a light emitting layer between the anode and the cathode, a hole injecting layer, a hole transporting layer, an electron blocking layer, an electron transporting layer, an electron injecting layer, and a hole blocking layer is formed by a vacuum deposition method or a solution process.
The method of claim 3,
Wherein the organic light emitting element is a display element, a display element, or an illumination element.






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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160036162A (en) * 2014-09-24 2016-04-04 에스에프씨 주식회사 An organoelectro luminescent compounds and organoelectro luminescent device using the same
WO2020159135A1 (en) * 2019-01-30 2020-08-06 덕산네오룩스 주식회사 Compound for organic electric element, organic electric element using same, and electronic device therefor

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20160036162A (en) * 2014-09-24 2016-04-04 에스에프씨 주식회사 An organoelectro luminescent compounds and organoelectro luminescent device using the same
WO2020159135A1 (en) * 2019-01-30 2020-08-06 덕산네오룩스 주식회사 Compound for organic electric element, organic electric element using same, and electronic device therefor

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