KR20140087250A - Ink composition for organic electronic device and organic electronic device comprising the same - Google Patents

Abstract

The present invention relates to an ink composition for an organic electronic device, including a compound represented by chemical formula 1 and an organic electronic device in which properties like efficiency, driving voltage, and span of life are improved using the ink composition. In chemical formula 1, R^1 to R^5, and X are defined as described in detailed description.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to an ink composition for an organic electronic device and an organic electronic device using the same.

The present invention relates to an ink composition for an organic electronic device containing an anthracene-based compound, and an organic electronic device having improved characteristics such as efficiency, driving voltage and lifetime by using the ink composition.

Background Art [0002] An organic electronic device is an electronic device using an organic semiconductor material, and requires the exchange of holes and / or electrons between the electrode and the organic semiconductor material. Organic electronic devices can be roughly classified into two types according to their operating principles. First, when a photon from an external light source flows into an organic material layer in an organic device, an exciton is formed in the organic material layer. After the exciton is separated into electrons and holes, the excitons are transferred to the different electrodes to be used as a current source . Second, when a voltage or an electric current is applied to two or more electrodes, holes and / or electrons are injected into the organic semiconductor material layer in contact with the electrodes, and the organic electronic device is operated by injected electrons and holes.

Examples of the organic electronic device include organic light emitting devices, organic solar cells, organic photoconductor (OPC) drums, and organic transistors. They all require an electron / hole injecting material, an electron / hole extracting material, an electron / hole transporting material or a light emitting material for driving the device, and these materials act on a similar principle in each organic electronic device.

Among the organic electronic devices, the organic light emitting device generally has a structure including a thin film organic material layer having an anode and a cathode, and a semiconductor characteristic interposed therebetween. When a voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the anode and electrons are injected into the organic layer, and excitons are generated when injected holes and electrons meet, When the exciton transitions from the excited state (LUMO) to the ground state (HOMO), the light in the visible region is emitted.

However, the display field is now becoming larger. In view of such a large-scale trend, when a large OLED is manufactured using a deposition process, the production yield is decreased due to an increase in substrate, investment is increased, and materials are consumed. In addition, since the monomolecular material is evaporated under vacuum in the vapor deposition process and deposited on the substrate, the HOMO and LUMO characteristics, energy (electron or hole) transfer characteristics, and the like Its use is limited due to its high transition temperature (Tg).

However, in the case of an ink composition used in various printing processes including inkjet, the luminous efficiency, luminance, power efficiency, thermal stability, and life span of the device are not satisfactory. For this reason, the printing process is disadvantageous in that it is more difficult to form a homogeneous nano-sized thin film than when a thin film is formed by vacuum deposition. In addition, And satellite ink droplets generated due to the problem of ink deteriorate the straightness and accuracy of the pattern at the time of printing and the uncertainty of the ink drying characteristic causes clogging of the ink jet head outlet and clustering of the wet film formed immediately after printing . Therefore, in order to solve such a problem, development of a new ink composition is continuously required.

The present invention provides an ink composition having excellent printability and an organic electronic device using the same, while improving the luminous efficiency, luminance, power efficiency, thermal stability, and life span of the device.

(A) a compound represented by the following general formula (1), (b) an aliphatic cyclic compound having 5 to 20 carbon atoms substituted with an atom-containing functional group selected from oxygen, sulfur and nitrogen; Aromatic ring compounds having 5 to 20 carbon atoms substituted with an atom-containing functional group selected from oxygen, sulfur and nitrogen; A heterocyclic compound having 5 to 20 nucleus atoms which is substituted with an atom-containing functional group selected from oxygen, sulfur and nitrogen or contains a hetero atom selected from oxygen, sulfur and nitrogen, (c) a first organic solvent selected from the group consisting of ) Is different from the first organic solvent and is an alcohol solvent, a ketone solvent, a cellosolve solvent, a carboxylic acid solvent, a carbitol solvent, an acetate solvent, a lactate solvent, an amine solvent, an ether solvent, A second organic solvent selected from the group consisting of an organic solvent, an aliphatic hydrocarbon solvent, and an amide solvent;

In Formula 1,

X is ^{CR 6 R 7, NR 6,} O, S, S (= O), S (= O) 2 and is selected from the group consisting of SiR ⁶ R ^7;

R ¹ to R ⁷ are the same or different from each other and each independently represents hydrogen, deuterium, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ An aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamino group, a C ₆ to C ₄₀ dia Reel amino group, C ₆ ~ C ₄₀ aryl group, C ₃ ~ C ₄₀ cycloalkyl group and nuclear atoms, or selected from the group consisting of a heterocycloalkyl group of 3 to 40, or adjacent groups bonded to the condensed aliphatic ring, a condensed aromatic A ring, a fused heteroaliphatic ring or a fused heteroaromatic ring;

In the above R ¹ to R ⁷ , a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, A C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamino group, a C ₆ to C ₄₀ diarylamino group, a C ₆ to C ₄₀ The arylalkyl group, the C ₃ to C ₄₀ cycloalkyl group and the heterocycloalkyl group having 3 to 40 nuclear atoms are each independently selected from the group consisting of deuterium, a halogen, a nitrile group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₁ ~ C ₄₀ of an amino group, an aryl group and the nucleus of a C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ cycloalkyl in the group, a number of nuclear atoms of 3 to 40 A heteroaryl group having 5 to 40 atoms and substituted or unsubstituted heteroaryl groups;

Two or more of R ¹ to R ⁴ are each independently a C ₆ to C ₄₀ aryl group.

The present invention also provides an organic electronic device comprising a first electrode, a second electrode, and at least one organic layer sandwiched between the first electrode and the second electrode, wherein at least one of the one or more organic layers And an organic thin film formed using the ink composition according to any one of claims 1 to 3.

Here, the organic thin film formed using the ink composition is preferably included in the light emitting layer.

The ink composition for an organic electronic device according to the present invention not only has excellent light emitting ability, but also excellent printability.

Therefore, when the ink composition according to the present invention is used as an organic material layer of an organic electronic device, preferably as a light emitting layer material, it is possible to obtain a large organic structure having a multilayer structure with improved luminous efficiency, luminance, power efficiency, thermal stability, It is possible to easily manufacture an electronic device, and further to manufacture a full color display panel in which the performance and life are greatly improved.

Hereinafter, the present invention will be described in detail.

The present invention relates to an ink composition for an organic electronic device, which comprises (a) a compound represented by the formula (1), (b) an aliphatic cyclic compound having 5 to 20 carbon atoms substituted with an atom-containing functional group selected from oxygen, sulfur and nitrogen; Aromatic ring compounds having 5 to 20 carbon atoms substituted with an atom-containing functional group selected from oxygen, sulfur and nitrogen; A heterocyclic compound having 5 to 20 nucleus atoms which is substituted with an atom-containing functional group selected from oxygen, sulfur and nitrogen or contains a hetero atom selected from oxygen, sulfur and nitrogen, (c) a first organic solvent selected from the group consisting of ) Is different from the first organic solvent and is an alcohol solvent, a ketone solvent, a cellosolve solvent, a carboxylic acid solvent, a carbitol solvent, an acetate solvent, a lactate solvent, an amine solvent, an ether solvent, And a second organic solvent selected from the group consisting of an organic solvent, an aliphatic hydrocarbon solvent, and an amide solvent. Such an ink composition not only has excellent light emitting ability but also can stably form an organic thin film. Therefore, it is possible to easily manufacture a large-sized organic electronic device having a multilayer structure with improved luminous efficiency, luminance, power efficiency, thermal stability, can do.

≪ Ink composition &

(a) a compound represented by the above formula (1)

The ink composition according to the present invention includes the compound represented by the above formula (1). The compound is a monomolecular fluorescent substance dissolved in the following first solvent, and has an energy gap between the conduction band and valence band of about 0.1 to 5 eV.

The compound represented by the formula (1) is an anthracene derivative, which is a core in which an anthracene moiety having excellent device characteristics and a fluorene moiety having excellent fluorescence properties are bonded together, for example, an indenoanthracene core , And the core is substituted with an aryl group.

R ¹ to R ⁷ are the same or different and each independently represents hydrogen, deuterium, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkenyl group, A C ₆ to C ₄₀ aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamino group, a C ₆ ~ diarylamino group of C _40, (aryl _{C 6 ~ C 40) C 1} ~ C 40 alkyl group, a heterocycloalkyl group of C ₃ ~ C ₄₀ cycloalkyl group and nuclear atoms, 3 to 40 of the ; Or may combine with adjacent groups to form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring.

In the above R ¹ to R ⁷ , a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, A C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamino group, a C ₆ to C ₄₀ diarylamino group, a C ₆ to C ₄₀ the arylalkyl group, C ₃ ~ C ₄₀ cycloalkyl group and nuclear atoms, heterocycloalkyl group of 3 to 40 are each independently a heavy hydrogen, a halogen, a nitrile group, a nitro group, an alkyl group of _{C 1 ~ C 40, C 2} ~ C 40 A C ₁ to C ₄₀ alkoxy group, a C ₁ to C ₄₀ amino group, a C ₃ to C ₄₀ cycloalkyl group, a heterocyclic cycloalkyl group having 3 to 40 nuclear atoms, a C ₆ to C ₄₀ aryl group, A heteroaryl group having 5 to 40 nuclear atoms, and a heteroaryl group having 5 to 40 nuclear atoms.

In addition, the R ¹ to R ⁷ wherein the C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₂ ~ C ₄₀ alkynyl group, C ₆ ~ C ₄₀ of the aryl group, the number of nuclear atoms of 5 to the A C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamino group, a C ₆ to C ₄₀ diarylamino group, a C ₆ to C ₄₀ the arylalkyl group, C ₃ ~ C ₄₀ cycloalkyl group and nuclear atoms, 3 to 40 heterocycloalkyl group C ₁ ~ C ₄₀ alkyl group in a substituent is introduced substituted in the, C ₂ ~ alkenyl group of C _40, C ₁ ~ for C ₄₀ alkoxy group, C ₁ ~ C ₄₀ of the amino group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and the number of nuclear atoms of 5 to 40 of the a heteroaryl group, each independently selected from deuterium, halogen, nitrile group, nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, an alkoxy group of _{C 1 ~ C 40, C 1} ~ amino groups of C ₄₀ , C cycloalkyl group of ₃ ~ C _40, nuclear In addition, or it may be substituted, or adjacent groups of binding to the one or more second substituent selected from the group consisting of is 3 to 40 heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and the number of nuclear atoms of 5 to 40 heteroaryl group of To form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring, or a spiro bond.

In the compound represented by the general formula (1), at least two of R ¹ to R ⁴ are each independently a C ₆ to C ₄₀ aryl group, and preferably two or more of R ¹ to R ⁴ are each independently Is a C ₆ to C ₄₀ aryl group selected from the group consisting of structural formulas of the following formula (2). Non-limiting examples, wherein R ¹ to R ⁴ of R ¹ and R ^2; Or R ³ and R ⁴ ; Or R ¹ , R ² and R ³ ; Or R ¹ , R ² and R ⁴ ; Or R ¹ , R ² , R ³ and R ⁴ are each independently a C ₆ to C ₄₀ aryl group selected from the group consisting of the following structural formula (2).

In Formula 2,

The Q ¹ to Q ⁴ is a group the same or different and each independently represent hydrogen, deuterium, halogen, nitrile each other, a nitro group, C ₁ ~ C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ of the alkoxy group, C ₁ ~ C ₄₀ group, C ₃ ~ C ₄₀ cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and a nuclear atoms group of 5 to 40 heteroaryl group Or may combine with adjacent groups to form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring.

Further, the Q ¹ to Q ⁴ alkoxy group of C ₁ ~ a C ₄₀ alkyl group, C ₂ ~ C ₄₀ alkenyl group, C ₁ ~ C ₄₀ of the in, C ₁ ~ C ₄₀ of the amino group, C ₃ ~ C ₄₀ the cycloalkyl group, the number of nuclear atoms of 3 to 40 heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and a nuclear atoms of 5 to 40 heteroaryl group, each independently selected from deuterium, halogen, nitrile group, nitro group, C ₁ ~ alkenyl of C ₄₀ alkyl group, C ₂ ~ C ₄₀ group, C ₁ ~ C ₄₀ alkoxy group, C ₁ ~ C ₄₀ group, C ₃ ~ C ₄₀ cycloalkyl group, a heterocycloalkyl group of nuclear atoms of 3 to 40 of the , optionally substituted additionally by one or more C ₆ ~ 3 substituents selected from an aryl group and the number of nuclear atoms of 5 to 40 heteroaryl group the group consisting of the C ₄₀ or may be unsubstituted.

As a non-limiting example, the C ₆ -C ₄₀ aryl group selected from the group consisting of the structural formula (2) may be selected from the group consisting of phenyl, biphenyl, terphenyl, naphthyl, anthracenyl, Phenanthryl, pyrenyl, fluorenyl, fluoranthenyl, perylenyl, and the like. These aryl groups are each independently selected from the group consisting of deuterium, a halogen, a nitrile group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₁ to C ₄₀ alkoxy group, a C ₁ to C ₄₀ amino group, C ₃ ~ C ₄₀ cycloalkyl group, nuclear atoms, 3 to 40 heterocycloalkyl group, C ₆ ~ C ₄₀ aryl group and a nuclear atoms or substituted by one or more selected from the group consisting of a heteroaryl group of from 5 to 40, Or may combine with adjacent groups to form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring or may form a spiro bond.

The following compounds are representative examples of the compound represented by the formula (1) of the present invention, but the compounds represented by the formula (1) of the present invention are not limited thereto.

The content of the compound represented by the general formula (1) is not particularly limited, and it is preferable to control the content depending on the kind of the solution coating method and the molecular weight of the compound. For example, the content of the compound represented by Formula 1 may be about 0.01 to 10% by weight, preferably about 0.1 to 5% by weight, more preferably about 0.1 to 5% by weight, 3% by weight.

The compound of Formula 1 can be synthesized according to a general synthetic method ( Chem. Rev. , 60 : 313 (1960), J. Chem. SOC . 4482 (1955), Chem. Rev. 95: 2457 Reference). Detailed synthesis of the compound of the present invention will be described in detail in the preparation examples described later.

(b) a first organic solvent

The ink composition according to the present invention comprises a first organic solvent. The first organic solvent can control the viscosity of the ink composition while dissolving the compound of formula (1).

The first organic solvent used in the present invention includes (i) an aliphatic cyclic compound having 5 to 20 carbon atoms substituted with an atom-containing functional group selected from oxygen, sulfur and nitrogen; (ii) an aromatic ring compound having 6 to 20 carbon atoms substituted with an atom-containing functional group selected from oxygen, sulfur and nitrogen; And (iii) a heterocyclic compound having 5 to 20 nuclear atoms, which is substituted by an atom-containing functional group selected from oxygen, sulfur and nitrogen, or contains a hetero atom selected from oxygen, sulfur and nitrogen, More than one species may be used in combination. Since such a first organic solvent contains oxygen, sulfur or nitrogen in the ring or contains an atom-containing functional group selected from oxygen, sulfur and nitrogen, it is preferable to use an aromatic ring compound such as benzene or an aromatic ring compound such as toluene Unlike the ring compound, the compound of formula (1) can be dissolved well. The first organic solvent may have a boiling point higher than that of the second organic solvent, and thus the first organic solvent may be mixed with the second organic solvent to change the viscosity of the ink composition during the formation of the organic layer by an ink- Not only the stability of the ink composition can be improved such that clogging is prevented but also the aggregation of the applied ink composition can be prevented.

Preferably, the first organic solvent is an aliphatic cyclic compound having 5 to 12 carbon atoms substituted with an atom-containing functional group selected from oxygen, sulfur and nitrogen; Aromatic ring compounds having 6 to 12 carbon atoms substituted with an atom-containing functional group selected from oxygen, sulfur and nitrogen; And heterocyclic compounds having 5 to 12 nucleus atoms which are substituted with an atom-containing functional group selected from oxygen, sulfur and nitrogen or contain a hetero atom selected from oxygen, sulfur and nitrogen. These heterocyclic compounds may be used singly or in combination of two or more. Can be mixed and used.

Specific examples of the first organic solvent include Methylcyclopentanol, Furan, Tetrahydrofuran, Tetrahydrofurfuryl alcohol, Pyrrole, Pyrrolidine, Pyrrolidone, Thiopene, Tetrahydrothiopene, Sulfolane, Pyran, Tetrahydropyran, Piperidine, Tetrahydropyran, Tetrahydrothiophene, But are not limited to, pyridine, trimethylpyridine, triethylpyridine, morpholine, anisole, and the like.

The boiling point of the first organic solvent is not particularly limited, but a low temperature process is possible when the temperature is in the range of about 150 to 350 ° C, preferably about 200 to 350 ° C, and more preferably 200 to 300 ° C.

Although the content of the first organic solvent is not particularly limited, since the first organic solvent controls the viscosity of the ink composition while dissolving the compound of the general formula (1), the content of the first organic solvent may vary depending on the content of the compound represented by the general formula (1) The content can be adjusted for viscosity control purposes of the desired ink composition. For example, the content of the first organic solvent may be adjusted in the range of about 50 to 99.9% by weight based on the total weight of the ink composition.

(c) a second organic solvent

The ink composition according to the present invention comprises a second organic solvent. The second organic solvent can control not only the viscosity of the ink composition, but also various properties such as hydrophilicity and hydrophobicity.

Examples of the second organic solvent used in the present invention include an alcohol solvent, a ketone solvent, a cellosolve solvent, a carboxylic acid solvent, a carbitol solvent, an acetate solvent, a lactate solvent, an amine solvent, A hydrocarbon-based solvent, an aliphatic hydrocarbon-based solvent, and an amide-based solvent. These solvents may be used alone or in combination of two or more. However, in the present invention, by using the second organic solvent different from the first organic solvent, it is possible to secure the viscosity and surface tension of the ink composition, which may be difficult to obtain by the first organic solvent, It is possible to prevent clogging or the like of the outlet of the inkjet print, and it is possible to prevent aggregation of the organic layer upon drying and firing.

Non-limiting examples of the alcohol solvent solvent include methanol, ethanol, propanol, isopropanol, butanol, isobutanol, pentanol, isopentanol, hexanol, heptanol, octanol, 3-hexanediol, 1,4-octanediol, and the like; Non-limiting examples of the ketone solvent solvent include acetone, methyl ethyl ketone, methyl butyl ketone, methyl propyl ketone, cyclohexanone, benzophenone, acetophenone, hexyl methyl ketone and the like; Examples of the solvent of the cellosolve solvent include methylcellosolve, ethylcellosolve, propylcellosolve and butylcellosolve. Nonlimiting examples of the solvent include ethylcarbitol, propylcellulose, Carbitol, butyl carbitol, and the like.

Non-limiting examples of the acetate solvent solvent include ethyl acetate, propyl acetate, butyl acetate, amyl acetate, hexyl acetate, ethyl carbitol acetate and the like; Non-limiting examples of the lactate solvent solvent include lactic acid, n-propyl lactate, isopropyl lactate, n-butyl lactate, isobutyl lactate, and 2-ethylhexyl lactate.

Examples of the amine-based solvent include propylamine, isopropylamine, butylamine, isobutylamine, amylamine, hexylamine, heptylamine, octylamine, 2-ethylhexylamine, nonylamine, decylamine, lauryl There may be mentioned amine compounds such as aminostearylamine, oleylamine, dibutylamine, diamylamine, dihexylamine, diheptylamine, dioctylamine, dinonylamine, didecylamine, dilaurylamine, But are not limited to, butylamine, triethylamine, trihexylamine, triheptylamine, trioctylamine, trinonylamine, tridecylamine, trilaurylamine, cyclohexylamine, pyridine, piperidine, morpholine, 1-naphthylamine, 1-naphthylamine, N-methylbenzylamine, ethylenediamine, N-dimethylbenzylamine, N-methylethylenediamine, N-propylethylenediamine, Diamine, N-propyl-1,3-propanediyl Amine, N-isopropyl-1,3-propanediamine, diethylenetriamine, N-dimethylethylenediamine, 3-methoxypropylamine, N-methylpyrrolidine, pyrrolidine and picoline. It is not limited.

Examples of the aromatic hydrocarbon solvent include toluene, xylene, ethylbenzene, benzene, nitrobenzene, and the like. Examples of the aromatic hydrocarbon solvent include, but are not limited to, tetrahydrofuran, anisole, Non-limiting examples of the aliphatic hydrocarbon solvent include cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, chloroform and the like. N, N-dimethylacetamide, N, N-dimethylformamide, and the like.

The boiling point of the second organic solvent is not particularly limited, but may be about 50 to 300 ° C, preferably about 150 to 300 ° C, more preferably about 200 to 250 ° C. At this time, two or more species having different boiling points may be mixed and used as the second organic solvent.

The content of the second organic solvent is not particularly limited, and it is appropriate to add the second organic solvent to such an extent that the compound of formula (1) dissolved in the ink composition does not elute. The content of the second organic solvent is preferably about 0.1 to 50 wt% , The viscosity and the surface tension of the ink composition, which is difficult to obtain with only the first organic solvent, can be secured at the same time.

(d) an aromatic ketone solvent

The ink composition according to the present invention may further comprise an aromatic ketone-based solvent. At this time, the aromatic ketone solvent used is different from the second organic solvent. The aromatic ketone solvent can improve the dissolution stability of the ink composition.

Examples of the aromatic ketone solvent that can be used in the present invention include a tetralone-based compound, specifically a C ₁ to C ₁₂ aliphatic hydrocarbon group, a C ₆ to C ₁₂ aryl group, a heteroaryl group having 5 to 12 nuclear atoms , Tetralone derivatives substituted or unsubstituted with halogen, and specific examples thereof include 1-tetralone, 2-tetralone, 2- (phenyl epoxy) tetralone, 6- (methoxy) And the like, but are not limited thereto. Examples of the aromatic ketone solvents other than the tetralone compounds include acetophenone (methyl phenyl ketone), propiophenone (ethyl phenyl ketone), benzophenone (diphenyl ketone) and derivatives thereof, but are not limited thereto.

The content of the aromatic ketone-based solvent is not particularly limited, and in consideration of the viscosity of the ink composition, the mixing ratio of the second organic solvent to the aromatic ketone solvent: second organic solvent = 1: 2: 2 to 1: It is appropriate to adjust. At this time, it is preferable that the total content of the aromatic ketone solvent and the second organic solvent is adjusted to be about 0.1 to 49% by weight based on the total weight of the ink composition.

(e) dopant material

The ink composition according to the present invention may further comprise a dopant material. The inclusion of the dopant material not only increases the color purity and increases the luminous efficiency through energy transfer but also eliminates the need to apply a dopant material separately in forming the light emitting layer of the device, thereby shortening the process. However, when the dopant material is not contained in the ink composition, the organic electroluminescent device may be formed by vacuum deposition, solution coating, or the like to form a light emitting layer.

Examples of the dopant include alkali metals, alkali metal complexes, alkali metal compounds, alkaline earth metals, alkaline earth metal complexes, alkaline earth metal compounds, rare earth metals, rare earth metal complexes, rare earth metal compounds, and halogen compounds and oxides thereof. These may be used alone or in combination of two or more.

Examples of the alkali metals include Li (work function: 2.93 eV), Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV), Cs And an alkali metal having a work function of 3.0 eV or less is preferable, and examples thereof include Li, K, Rb and Cs.

Examples of the alkaline earth metal include Ca (work function: 2.9 eV), Sr (work function: 2.0 to 2.5 eV), Ba (work function: 2.52 eV) and the like, and an alkaline earth metal having a work function of 3.0 eV or less .

Examples of the rare earth metal include Sc, Y, Ce, Tb and Yb, and a rare earth metal having a work function of 3.0 eV or less is preferable.

Among these metals, a preferable metal has a particularly high reducing ability, so that by adding a relatively small amount of metal to the electron injecting region, the light emission intensity of the organic EL device can be improved and the lifetime can be prolonged.

Examples of the alkali metal compound include alkali oxides such as Li ₂ O, Cs ₂ O, or K ₂ O; Alkali halides such as LiF, NaF, CsF, KF and the like, and alkali oxides or alkali fluorides such as LiF, Li ₂ O or NaF are preferable.

Examples of the alkaline earth metal compound include BaO, SrO, CaO, and mixtures thereof such as Ba _x Sr _1-x O (0 <x <1) and Ba _x Ca _1-x O (0 < Among these, BaO, SrO and CaO are preferable.

Examples of the rare-earth metal compound include YbF ₃ , ScF ₃ , ScO ₃ , Y ₂ O ₃ , Ce ₂ O ₃ , GdF ₃ and TbF _3. Of these, YbF ₃ , ScF ₃ and TbF ₃ are preferable.

The alkali metal complex, alkaline earth metal complex and rare earth metal complex are not particularly limited as long as they each contain one or more alkali metal ions, alkaline earth metal ions and rare earth metal ions as metal ions. Also, preferred examples of the ligand include quinoline, benzoquinoline, aciridine, phenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyadiryloxadiazole, hydroxyadirylthiadiazole , Hydroxyphenyl benzoimidazole, hydroxybenzotriazole, hydroxy fl uorene, bipyridyl, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene, beta-diketones, azomethanes , And derivatives thereof, but are not limited thereto.

The content of the dopant material is not particularly limited, but may be about 1 to 99% by weight, preferably about 1 to 30% by weight, more preferably about 5 to 20% by weight, based on the total weight of the dry solid film . Here, the dry thin film means a thin film formed by applying and drying an ink composition.

(f) Additive

If necessary, the ink composition according to the present invention may contain, in addition to the compound of the formula (1), the first organic solvent and the second organic solvent, an antifoaming agent for removing air bubbles in the ink composition A leveling agent which contributes to planarization in the formation of the organic layer, a slip agent which improves the printability in the contact-type printing process of the substrate surface, a wetting agent which improves the adhesion of the organic layer to the substrate surface, a thickener for improving the viscosity of the ink composition and improving the formation of the organic layer, a surfactant, and the like. It may further include a polymer material such as an acrylic resin, a modified acrylic resin, an epoxy resin, a modified epoxy resin, a urethane resin, a modified urethane resin, a silicone resin, a modified silicone resin, a fluorocarbon resin, or a modified fluorocarbon resin .

The content of the additive is not particularly limited, but is suitably used within a range that does not deteriorate the properties of the dried organic layer. For example, it is about 0.001 to 1% by weight, preferably about 0.001 to 0.1% by weight.

On the other hand, the ink composition of the present invention can be produced through various methods.

According to an embodiment of the present invention, the ink composition may be prepared by dissolving the compound represented by Formula 1 in the first organic solvent and then adding the second organic solvent. When the second organic solvent is added, an aromatic ketone solvent and / or a dopant material may be further added. In addition, the above-mentioned one or more additives may be further added.

The viscosity of the ink composition described above is preferably adjusted by suitably selecting the kind and content of the compound represented by Chemical Formula 1 and the first and second organic solvents according to the solution coating method. For example, from about 1 to 100 cps, and preferably from about 3 to 50 cps. According to one example of the present invention, when the organic layer is formed by inkjet printing, the viscosity of the ink composition may be adjusted to about 3 to 25 cps, preferably about 3 to 20 cps.

The surface tension of the ink composition varies depending on the kind of the compound represented by Chemical Formula 1 and the kind of the first and second organic solvents and is about 1 to 100 dyne / cm ² , preferably about 10 to 60 dyne / cm ² , Preferably about 15 to 40 dyne / cm &lt; ² &gt;.

&Lt; Organic electronic device &

The present invention provides an organic electronic device, preferably an organic electroluminescent device, using the ink composition described above.

The organic electronic device according to the present invention includes a first electrode, a second electrode, and at least one organic layer sandwiched between the first electrode and the second electrode, And an organic thin film formed using the composition.

The method for producing an organic electronic device of the present invention is characterized in that the ink composition is applied onto a substrate through a known solution coating method and then the coating layer is cured by light irradiation or heat treatment to form one or more organic layer Can be produced by a conventional method and material for producing an organic electronic device. Examples of the solution coating method include a spin coating method, a dip coating method, an ink jet printing method, a screen printing method, a gravure printing method, a flexo printing method, a slot die coating method, a coating method using a doctor blade, And the like, but are not limited thereto.

Examples of such organic electronic devices include an organic electroluminescent device, an organic field effect transistor (OFET), an organic thin film transistor (OTFT), an organic photoconductor (OPC) drum, an organic photovoltaic device, and an organic solar cell.

Hereinafter, the organic electroluminescent device of the organic electronic device will be described.

The organic electroluminescent device includes an anode, a cathode, and one or more organic layers sandwiched between the anode and the cathode.

The at least one organic material layer may be at least one of a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer and an electron injecting layer, and at least one of the organic layers may include an organic thin film formed using the ink composition, The light emitting layer may include an organic thin film formed using the ink composition. When the organic thin film formed using the ink composition is included in the organic material layer of the organic electroluminescent device, the efficiency (luminous efficiency and power efficiency), lifetime, brightness and driving voltage of the device can be improved.

The structure of the organic electroluminescent device is not particularly limited and may be a structure in which a substrate, an anode, a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and a cathode are sequentially laminated. At least one of the hole injecting layer, the hole transporting layer, the light emitting layer, the electron transporting layer, and the electron injecting layer may include an organic thin film formed of the ink composition. Preferably, the light emitting layer includes an organic thin film formed of the ink composition . In some cases, an electron injecting layer may be further stacked on the electron transporting layer. Further, an insulating layer or an adhesive layer may be further inserted into the interface between the electrode and the organic material layer.

The organic electroluminescent device according to the present invention can be formed by using materials and methods known in the art, except that at least one of the organic layers (for example, a light emitting layer) is formed by solution coating of the ink composition. And forming an electrode.

Other organic layers not formed with the ink composition may be formed by a vacuum evaporation method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

The substrate usable in the present invention is not particularly limited, and a silicon wafer, quartz, a glass plate, a metal plate, a plastic film and a sheet can be used.

Examples of the positive electrode material include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO _2: a combination of a metal and an oxide such as Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.

The negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin or lead or an alloy thereof; And multi-layer structure materials such as LiF / Al or LiO ₂ / Al, but are not limited thereto.

As the hole injecting material, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material is between the work function of the anode material and the HOMO of the surrounding organic layer . Specific examples of the hole injecting material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.

The hole transporting material may be a material capable of transporting holes from the anode or the hole injecting layer to the light emitting layer and having high mobility with respect to holes. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.

As the electron transporting material, a material capable of transferring electrons from the cathode well into the light emitting layer, which is suitable for electrons, is suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq ₃ ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.

The organic electroluminescent device according to the present invention may be a front emission type, a back emission type, or a both-sided emission type, depending on the material used.

The ink composition according to the present invention may act on a principle similar to that applied to organic electroluminescent devices in other organic electronic devices such as organic solar cells, organophotoreceptors, and organic transistors.

Hereinafter, the present invention will be described in detail with reference to the following examples. However, the following examples are illustrative of the present invention, and the present invention is not limited by the following examples.

[ Synthetic example  1-1] intermediate EMI  Synthesis of 1

<Step 1> Bromo -2- (7- bromo -9,9- dimethyl -9H- 불소 -2- carbonyl ) - benzoic  Synthesis of acid

40 g (1 eq, 0.146 mol) of Bromo-9,9-dimethyl-9H-fluorene and 36.5 g (1.1 eq, 0.161 mol) of 2-bromo phthalic anhydride were placed in a reaction vessel and 1.5 L of dichloromethane was added. 29.2 g (1.5 eq, 0.219 mol) of aluminum chloride was gradually added at 0 ° C, and then the temperature was raised to room temperature, followed by stirring for 12 hours. After the completion of the reaction, distilled water was slowly added to the reaction mixture at 0 ° C, excess dichloromethane was extracted and washed several times with distilled water. After removing the solvent, the resulting solid was washed and placed in a Hexane 2 liter container. The solution was filtered and dried to obtain 59.8 g of a bromo-2- (7-bromo-9,9-dimethyl-9H-fluorene-2-carbonyl) &Lt; / RTI &gt;

^{1 H-NMR: 8.44 (t} , 2H), 8.23 (d, 1H), 7.96 (m, 5H), 7.72 (m, 5H), 7.55 (t, 1H), 1.67 (s, 6H)

Step 2 Synthesis of 9-bromo-13,13-dimethyl-6H-indeno [1,2-b] anthracene-6,11 (13H)

20 g (1 eq, 0.0399 mol) of Bromo-2- (7-bromo-9,9-dimethyl-9H-fluorene-2-carbonyl) -benzoic acid was placed in a flask and 50 ml of polyphosphoric acid was added. Followed by heating and stirring at 140 DEG C for 2 hours. After cooling to 50 ° C or less, distilled water was slowly added. The resulting solid was filtered and washed with a small amount of methanol and dried to obtain 15 g of 9-bromo-13,13-dimethyl-6H-indeno [1,2-b] anthracene-6,11 (13H) %).

^{1 H-NMR: 8.29 (t} , 3H), 8.09 (s, 2H), 7.85 (d, 2H), 7.72 (m, 2H), 1.67 (s, 6H)

Step 3: Preparation of 9-bromo-13,13-dimethyl-6,11-di (naphthalen-2-yl) -11,13-dihydro-6H- indeno [1,2- b] anthracene- Synthesis of

4.96 g (2.2 eq, 0.054 mol) of 2-bromonaphthrene was added to the flask, and 200 ml of THF was added to dissolve. 38.4 ml (2.5 eq, 0.06 mol) of n-BuLi was slowly added dropwise at -78 deg. After stirring for 1 hour, 11.8 g (1 eq, 0.024 mol) of 9-dibromo-13,13-dimethyl-6H-indeno [1,2- b] anthracene-6,11 (13H) -dione was added. And the mixture was stirred at room temperature for 17 hours. After completion of the reaction, the reaction mixture was extracted with washing water and ethyl acetate using distilled water and then subjected to column chromatography to obtain 9-dibromo-13,13-dimethyl-6,11-di (naphthalen- 1,2-b] anthracene-6,11-diol (yield = 78%).

^{1 H-NMR: 8.02 (d} , 3H), 7.95 (d, 2H), 7.61 (s, 2H), 7.64 (m, 9H), 7.46 (s, 2H), 7.19 (d, 2H), 1.67 (s , 6H)

Synthesis of 9-bromo-13,13-dimethyl-6,11-di (naphthalen-2-yl) -13H-indeno [1,2- b] anthracene (EMI-1)

9-dibromo-13,13-dimethyl-6,11-di (naphthalen-2-yl) -11,13-dihydro-6H- indeno [1,2- b] anthracene- 21.58g (10eq, 0.13mol) of Potasuumiodide and 19.61g (16.5eq, 0.223mol) of sodium hypophosphite were placed in a flask and 500ml of Acetic acid was added. Followed by heating and stirring for 5 hours. After reaction, the reaction solution was added to an excess amount of distilled water to form a solid, washed and then filtered and subjected to column chromatography to obtain 9-dibromo-13,13-dimethyl-6,11-di (naphthalen-2-yl) [1,2-b] anthracene (EMI 1) (yield = 76%).

^{1 H-NMR: 8.11 (d} , 3H), 8.02 (d, 2H), 7.95 (d, 2H), 7.61 (s, 2H), 7.64 (m, 4H), 7.46 (s, 2H), 7.19 (d , &Lt; / RTI &gt; 2H), 1.67 (s, 6H)

[ Synthetic example  1-2] Intermediate EMI  Synthesis of 2

Intermediate EMI 2 was obtained in Step 3 of Synthesis Example 1-1 using 2-bromo-9,9-dimethyl-9H-fluorene instead of 2-bromonaphthrene.

Elemental Analysis: C, 84.00; H, 5.45; Br, 10.54 / HRMS [M] &lt; ⁺ & gt ^; : 758

[ Synthetic example  1-3] Intermediate EMI  Synthesis of 3

In Step 3 of Synthesis Example 1-1, EMI3 was obtained using 4-bromobiphenyl instead of 2-bromonaphthrene.

Elemental Analysis: C, 83.3; H, 4.91, Br, 11.7 / HRMS [M] &lt; ⁺ & gt ^; : 678.

[ Synthetic example  1-4] Intermediate EMI 4 of  synthesis

Intermediate EMI 4 was obtained by using 3-bromofluoranthene instead of 2-bromonaphthrene in Step 3 of Synthesis Example 1-1.

Elemental Analysis: C, 85.37; H, 4.30, Br, 10.33 / HRMS [M] ⁺ : 774

[ Synthetic example  1-5] Compound Inv  Synthesis of 1-1

10 g (1 eq) of 9-dibromo-13,13-dimethyl-6,11-di (naphthalen-2-yl) -13H- indeno [1,2- b] anthracene (Intermediate EMI 1) 0.016mol) and naphthalen-2-ylboronic acid 3.2g ( 1.2eq, 0.019mol), Pd (PPh 3) 4 0.65g (0.03eq, 5.7mmol) were placed in the flask 2M K ₂ CO ₃ saturated aqueous solution and 15ml Toluene 150ml And the mixture was heated and stirred for 12 hours. After completion of the reaction, the reaction mixture was filtered through Celite and then extracted with MC to obtain final compound Inv 1-1 (13,13-dimethyl-6,9,11-tri (naphthalen-2-yl) 13H-indeno [1,2-b] anthracene) (yield = 88.7%).

Inv 1-1: Elemental Analysis: C, 94.61; H, 5.39 / HRMS [M] &lt; ⁺ & gt ^; : 672.

[Synthesis Example 1-6 to Synthesis Example 1-24] Synthesis of Compound Inv 1-2 to Compound Inv 1-20

Synthesis was carried out using the same method as in the synthesis of Compound Inv 1-1 of Synthesis Example 1-5, and it was obtained as a pale yellow solid.

Inv 1-2: Elemental Analysis: C, 94.61; H, 5.39 / HRMS [M] &lt; ⁺ & gt ^; : 672.

Inv 1-3: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] &lt; ⁺ & gt ^; : 772

Inv 1-4: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] &lt; ⁺ & gt ^; : 722

Inv 1-5: Elemental Analysis: C, 94.52; H, 5.48 / HRMS [M] &lt; ⁺ & gt ^; : 698

Inv 1-6: Elemental Analysis: C, 94.52; H, 5.48 / HRMS [M] &lt; ⁺ & gt ^; : 698

Inv 1-7: Elemental Analysis: C, 94.52; H, 5.48 / HRMS [M] &lt; ⁺ & gt ^; : 698

Inv 1-8: Elemental Analysis: C, 94.27; H, 5.73 / HRMS [M] &lt; ⁺ & gt ^; : 738

Inv 1-9: Elemental Analysis: C, 94.85; H, 5.15 / HRMS [M] &lt; ⁺ & gt ^; : 860

Inv 1-10: Elemental Analysis: C, 94.62; H, 5.38 / HRMS [M] &lt; ⁺ & gt ^; : 748

Inv 1-11: Elemental Analysis: C, 94.62; H, 5.38 / HRMS [M] &lt; ⁺ & gt ^; : 748

Inv 1-12: Elemental Analysis: C, 94.62; H, 5.38 / HRMS [M] &lt; ⁺ & gt ^; : 748

Inv 1-13: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] &lt; ⁺ & gt ^; : 798

Inv 1-14: Elemental Analysis: C, 94.78; H, 5.22 / HRMS [M] &lt; ⁺ & gt ^; : 848

Inv 1-15: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] &lt; ⁺ & gt ^; : 799

Inv 1-16: Elemental Analysis: C, 94.62; H, 5.38 / HRMS [M] &lt; ⁺ & gt ^; : 748

Inv 1-17: Elemental Analysis: C, 94.87; H, 5.13, HRMS [M] &lt; ⁺ & gt ^; : 746

Inv 1-18: Elemental Analysis: C, 94.94; H, 5.06 / HRMS [M] &lt; ⁺ & gt ^; : 796

Inv 1-19: Elemental Analysis: C, 94.62; H, 5.38 / HRMS [M] &lt; ⁺ & gt ^; : 748

Inv 1-20: Elemental Analysis: C, 94.62; H, 5.38 / HRMS [M] &lt; ⁺ & gt ^; : 748

[Synthesis Example 1-25] Synthesis of Compound Inv 1-21

(9,9-dimethyl-9H-fluoren-2-yl) -13,13-dimethyl-13H-indeno [1,2-b] anthracene intermediate EMI 2) 10g (1eq, 0.014mol ) and naphthalen-2-ylboronic acid 3.0g ( 1.2eq, 0.016mol), Pd (PPh 3) 4 0.6g ( placed in the flask a 0.03eq, 5.1mmol) 2M K ₂ CO ₃ saturated aqueous solution (15 ml) and toluene (150 ml), and the mixture was heated and stirred for 12 hours. After completion of the reaction, the reaction solution was filtered through Celite and then extracted with MC to obtain 9.3 g (yield: 83%) of the final compound Inv 1-21 through column chromatography.

Inv 1-21: Elemental Analysis: C, 93.99; H, 6.01 / HRMS [M] &lt; ⁺ & gt ^; : 804

[Synthesis Example 1-26 to Synthesis Example 1-44] Synthesis of Compound Inv 1-22 to Compound Inv 1-40

Synthesis was carried out using the same method as the synthesis of Compound Inv 1-21 synthesized in Synthesis Example 1-25, and it was obtained as a pale yellow solid.

Inv 1-22: Elemental Analysis: C, 93.99; H, 6.01 / HRMS [M] &lt; ⁺ & gt ^; : 804

Inv 1-23: Elemental Analysis: C, 94.11; H, 5.89 / HRMS [M] &lt; ⁺ & gt ^; : 854

Inv 1-24: Elemental Analysis: C, 94.11; H, 5.89 / HRMS [M] &lt; ⁺ & gt ^; : 854

Inv 1-25: Elemental Analysis: C, 93.94; H, 6.06 / HRMS [M] &lt; ⁺ & gt ^; : 830

Inv 1-26: Elemental Analysis: C, 93.94; H, 6.06 / HRMS [M] &lt; ⁺ & gt ^; : 830

Inv 1-27: Elemental Analysis: C, 93.94; H, 6.06 / HRMS [M] &lt; ⁺ & gt ^; : 830

Inv 1-28: Elemental Analysis: C, 93.75; H, 6.25 / HRMS [M] &lt; ⁺ & gt ^; : 870

Inv 1-29: Elemental Analysis: C, 94.32; H, 5.68 / HRMS [M] &lt; ⁺ & gt ^; : 992

Inv 1-30: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] &lt; ⁺ & gt ^; : 880

Inv 1-31: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] &lt; ⁺ & gt ^; : 880

Inv 1-32: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] &lt; ⁺ & gt ^; : 880

Inv 1-33: Elemental Analysis: C, 94.16; H, 5.84 / HRMS [M] &lt; ⁺ & gt ^; : 930

Inv 1-34: Elemental Analysis: C, 94.25; H, 5.75 / HRMS [M] &lt; ⁺ & gt ^; : 980

Inv 1-35: Elemental Analysis: C, 94.16; H, 5.84 / HRMS [M] &lt; ⁺ & gt ^; : 930

Inv 1-36: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] &lt; ⁺ & gt ^; : 880

Inv 1-37: Elemental Analysis: C, 94.27; H, 5.73 / HRMS [M] &lt; ⁺ & gt ^; : 878

Inv 1-38: Elemental Analysis: C, 94.36; H, 5.64 / HRMS [M] &lt; ⁺ & gt ^; : 928

Inv 1-39: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] &lt; ⁺ & gt ^; : 880

Inv 1-40: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] &lt; ⁺ & gt ^; : 880

[Synthesis Example 1-45] Synthesis of Compound Inv 1-41

(9,9-dimethyl-9H-fluoren-2-yl) -13,13-dimethyl-13H-indeno [1,2-b] anthracene intermediate EMI 3) 10g (1eq, 0.014mol ) and naphthalen-2-ylboronic acid 3.0g ( 1.2eq, 0.016mol), Pd (PPh 3) 4 0.6g ( placed in the flask a 0.03eq, 5.1mmol) 2M K ₂ CO ₃ saturated aqueous solution (15 ml) and toluene (150 ml), and the mixture was heated and stirred for 12 hours. After completion of the reaction, the reaction solution was filtered through Celite and then extracted with MC to obtain 9.3 g (yield: 83%) of final compound Inv 1-41 through column chromatography.

Inv 1-41: Elemental Analysis: C, 93.99; H, 6.01 / HRMS [M] &lt; ⁺ & gt ^; : 804

[Synthesis Example 1-46 to Synthesis Example 1-54] Synthesis of Compound Inv 1-42 to Compound Inv 1-50

Synthesis was carried out using the same method as that of the compound Inv 1-41 of Synthesis Example 1-45, and it was obtained as a pale yellow solid.

Inv 1-42: Elemental Analysis: C, 93.99; H, 6.01 / HRMS [M] &lt; ⁺ & gt ^; : 804

Inv 1-43: Elemental Analysis: C, 94.54; H, 5.46 / HRMS [M] &lt; ⁺ & gt ^; : 774

Inv 1-44: Elemental Analysis: C, 94.36; H, 5.64 / HRMS [M] &lt; ⁺ & gt ^; : 750

Inv 1-45: Elemental Analysis: C, 94.14; H, 5.86 / HRMS [M] &lt; ⁺ & gt ^; : 790

Inv 1-46: Elemental Analysis: C, 94.36; H, 5.64 / HRMS [M] &lt; ⁺ & gt ^; : 750

Inv 1-47: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] &lt; ⁺ & gt ^; : 912

Inv 1-48: Elemental Analysis: C, 94.46; H, 5.54 / HRMS [M] &lt; ⁺ & gt ^; : 800

Inv 1-49: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] &lt; ⁺ & gt ^; : 799

Inv 1-50: Elemental Analysis: C, 94.78; H, 5.22 / HRMS [M] &lt; ⁺ & gt ^; : 848

[ Synthetic example  1-55] Compound Inv  Synthesis of 1-51

10 g (1 eq, 0.012 mol) of the 9-bromo-6,11-di (fluoranthen-3-yl) -13,13-dimethyl-13H- indeno [1,2- b] anthracene mol) and naphthalen-2-ylboronic acid 2.9g ( 1.2eq, 0.015mol), Pd (PPh 3) 4 0.52g (0.03eq, 4.6mmol) were placed in the flask 2M K ₂ CO ₃ saturated aqueous solution and 15ml Toluene 150ml And the mixture was heated and stirred for 12 hours. After completion of the reaction, the reaction mixture was filtered through Celite and then extracted with MC to obtain 7.8 g (yield: 80%) of final compound Inv 1-51 through column chromatography.

Inv 1-51: Elemental Analysis: C, 95.09; H, 4.91 / HRMS [M] &lt; ⁺ & gt ^; : 820

[Synthesis Example 1-56 to Synthesis Example 1-64] Synthesis of Compound Inv 1-52 to Compound Inv 1-60

Synthesis was carried out using the same method as that of the compound Inv 1-51 of Synthesis Example 1-55, and it was obtained as a pale yellow solid.

Inv 1-52: Elemental Analysis: C, 94.78; H, 5.22 / HRMS [M] &lt; ⁺ & gt ^; : 848

Inv 1-53: Elemental Analysis: C, 95.14; H, 4.86 / HRMS [M] &lt; ⁺ & gt ^; : 870

Inv 1-54: Elemental Analysis: C, 95.00; H, 5.00 / HRMS [M] &lt; ⁺ & gt ^; : 846

Inv 1-55: Elemental Analysis: C, 94.77; H, 5.23 / HRMS [M] &lt; ⁺ & gt ^; : 886

Inv 1-56: Elemental Analysis: C, 95.00; H, 5.00 / HRMS [M] &lt; ⁺ & gt ^; : 846

Inv 1-57: Elemental Analysis: C, 95.21; H, 4.79 / HRMS [M] &lt; ⁺ & gt ^; : 1008

Inv 1-58: Elemental Analysis: C, 95.06; H, 4.94 / HRMS [M] &lt; ⁺ & gt ^; : 896

Inv 1-59: Elemental Analysis: C, 95.27; H, 4.73 / HRMS [M] &lt; ⁺ & gt ^; : 894

Inv 1-60: Elemental Analysis: C, 95.31; H, 4.69 / HRMS [M] &lt; ⁺ & gt ^; : 944

[ Synthetic example  2-1] intermediate EMI  Synthesis of 5

<Step 1> 2- (7- bromo -9,9- dimethyl -9H- 불소 -2- carbonyl ) benzoic acid  synthesis

40 g (1 eq, 0.146 mol) of 2-bromo-9,9-dimethyl-9H-fluorene and 23.8 g (1.1 eq, 0.161 mol) of phthalic anhydride were placed in a reaction vessel and 1 liter of dichloromethane was added. 29.2 g (1.5 eq, 0.219 mol) of aluminum chloride was gradually added at 0 ° C, and then the temperature was raised to room temperature, followed by stirring for 12 hours. After the completion of the reaction, distilled water was slowly added to the reaction mixture at 0 ° C, excess dichloromethane was extracted and washed several times with distilled water. After removing the solvent, the resulting solid was washed in a Hexane 2 liter container, and then filtered and dried to obtain 50.4 g of 2- (7-bromo-9,9-dimethyl-9H-fluorene-2-carbonyl) benzoic acid in a yield of 82%.

¹ H-NMR: 8.44 (t, IH), 8.23 (d, IH), 7.96 (m, 6H), 7.72 (m, 5H), 7.55 (t,

Step 2 Synthesis of 2-bromo-13,13-dimethyl-6H-indeno [1,2-b] anthracene-6,11 (13H)

20 g (1 eq, mol) of 2- (7-bromo-9,9-dimethyl-9H-fluorene-2-carbonyl) benzoic acid was added to the flask and 50 ml of polyphosphoric acid was added. And heated at 140 DEG C for 2 hours. After cooling to 50 ° C or less, distilled water was slowly added. The resulting solid was filtered and washed with a small amount of methanol and dried to obtain 16.6 g of 2-bromo-13,13-dimethyl-6H-indeno [1,2-b] anthracene-6,11 (13H) 81%).

^{1 H-NMR: 8.29 (t} , 2H), 8.09 (s, 2H), 7.85 (d, 2H), 7.72 (m, 3H), 1.67 (s, 6H)

Step 3: Preparation of 2-bromo-13,13-dimethyl-6,11-di (naphthalen-2-yl) -11,13-dihydro-6H- indeno [1,2- b] anthracene- Synthesis of

2-Bromonaphthrene 4.96 g (2.2 eq, 0.054 mol) was added to the flask and dissolved in 200 ml THF. 38.4 ml (2.5 eq, 0.06 mol) of n-BuLi was slowly added dropwise at -78 deg. After stirring for 1 hour, 2-bromo-13,13-dimethyl-6H-indeno [1,2-b] anthracene-6,11 (13H) -dione, 10 g (1 eq, 0.024 mol) was added. And the mixture was stirred at room temperature for 17 hours. After completion of the reaction, the reaction mixture was extracted with distilled water and extracted with ethyl acetate. Then, 2-bromo-13,13-dimethyl-6,11-di- 1,2-b] anthracene-6,11-diol (yield = 72%).

^{1 H-NMR: 8.02 (d} , 2H), 7.95 (d, 2H), 7.61 (s, 2H), 7.64 (m, 10H), 7.46 (s, 2H), 7.19 (d, 2H), 1.67 (s , 6H)

Synthesis of 2-bromo-13,13-dimethyl-6,11-di (naphthalen-2-yl) -13H-indeno [1,2- b] anthracene (EMI-5)

2-bromo-13,13-dimethyl-6,11-di (naphthalen-2-yl) -11,13-dihydro-6H- indeno [1,2- b] anthracene- (10eq, 0.075mol) and 6g (5eq, 0.037mol) of sodium hypophosphite were placed in a flask and 200ml of acetic acid was added. Followed by heating and stirring for 5 hours. After the reaction, the reaction mixture was added to an excess amount of distilled water to form a solid, washed, and then filtered and subjected to column chromatography to obtain 3.56 g (yield = 76%).

^{1 H-NMR: 8.11 (d} , 2H), 8.02 (d, 2H), 7.95 (d, 2H), 7.61 (s, 2H), 7.64 (m, 5H), 7.46 (s, 2H), 7.19 (d , &Lt; / RTI &gt; 2H), 1.67 (s, 6H)

[ Synthetic example  2-2] Intermediate EMI  Synthesis of 6

EMI-6 was obtained using 2-bromo-9,9-dimethyl-9H-fluorene instead of 2-bromonaphthrene used in Step 3 of Synthesis Example 2-1.

Elemental Analysis: C, 84.00; H, 5.45; Br, 10.54 / HRMS [M] &lt; ⁺ & gt ^; : 758.

[ Synthetic example  2-3] Intermediate EMI 7's  synthesis

EMI-7 was obtained using 4-bromobiphenyl instead of 2-bromonaphthrene used in <Step 3> of Synthesis Example 2-1.

Elemental Analysis: C, 83.3; H, 4.91, Br, 11.79 / HRMS [M] &lt; ⁺ & gt ^; : 678.

[ Synthetic example  2-4] Intermediate EMI 8 of  synthesis

EMI-8 was obtained using 3-bromofluoranthene instead of 2-bromonaphthrene used in < Step 3 > in Synthesis Example 2-1.

Elemental Analysis: C, 85.37; H, 4.30, Br, 10.33 / HRMS [M] ⁺ : 774

[Synthesis Example 2-5] Synthesis of Compound Inv 2-1

10 g (1 eq, 0.014) of the 2-bromo-13,13-dimethyl-6,11-di (naphthalen-2-yl) -13H- indeno [1,2- b] anthracene mol) and naphthalen-2-ylboronic acid 3.0g ( 1.2eq, 0.016mol), Pd (PPh 3) 4 0.6g (0.03eq, 5.1mmol) were placed in the flask 2M K ₂ CO ₃ saturated aqueous solution and 15ml Toluene 150ml put After dissolving, the mixture was heated and stirred for 12 hours. After completion of the reaction, the reaction solution was filtered through Celite and then extracted with MC to obtain 9.3 g (yield: 83%) of final compound Inv 2-1 through column chromatography.

¹ H-NMR: 8.11 (d, 3H), 8.02 (d, 3H), 7.95 (m, 3H), 7.61 (m, 5H) , &Lt; / RTI &gt; 2H), 1.67 (s, 6H).

Elemental Analysis: C, 94.61; H, 5.39 / HRMS [M] &lt; ⁺ & gt ^; : 672.

[Synthesis Example 2-6] Synthesis of Compound Inv 2-2

10 g (1 eq, 0.014) of 2-bromo-13,13-dimethyl-6,11-di (naphthalen-2-yl) -13H- indeno [1,2- b] anthracene mol) and 10- (naphthalen-2-yl) anthracen-9-ylboronic acid 6.5g (1.2eq, 0.016mol), Pd (PPh 3) 4 0.6g ( placed in the flask a 0.03eq, 5.1mmol) 2M K ₂ CO ₃ saturated aqueous solution (15 ml) and toluene (150 ml), and the mixture was heated and stirred for 12 hours. After completion of the reaction, the reaction solution was filtered through Celite and then extracted with MC to obtain 10.4 g (yield: 82%) of the final compound Inv 2-2 through column chromatography.

¹ H-NMR: 8.11 (m, 6H), 7.95 (m, 6H), 7.61 (m, 4H), 7.64 , 6H).

Elemental Analysis: C, 94.61; H, 5.39 / HRMS [M] &lt; ⁺ & gt ^; : 672.

[Synthesis Example 2-7] Synthesis of Compound Inv 2-3

10 g (1 eq, 0.014) of the 2-bromo-13,13-dimethyl-6,11-di (naphthalen-2-yl) -13H- indeno [1,2- b] anthracene mol) and 3- (naphthalen-2-yl) phenylboronic acid 4.7g (1.2eq, 0.016mol), Pd (PPh 3) 4 0.6g (0.03eq, 5.1mmol) were placed in the flask 2M K ₂ CO ₃ saturated aqueous solution And 150 ml of toluene, and the mixture was heated and stirred for 12 hours. After completion of the reaction, the reaction solution was filtered through Celite and then extracted with MC to obtain 9.9 g (yield: 88%) of the final compound Inv 2-3 by column chromatography.

¹ H-NMR: 8.11 (m, 6H), 7.95 (m, 6H), 7.61 (m, 4H), 7.64 , &Lt; / RTI &gt; 4H), 1.67 (s, 6H).

Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] &lt; ⁺ & gt ^; : 772

[Synthesis Example 2-8 to Synthesis Example 2-16] Synthesis of Compound Inv 2-4 to Compound Inv 2-12

Synthesis was carried out using the same method as the synthesis of Inv 2-1 of the compound of Synthesis Example 2-5, and it was obtained as a pale yellow solid.

Inv 2-4: Elemental Analysis: C, 94.52; H, 5.48 / HRMS [M] &lt; ⁺ & gt ^; : 698

Inv 2-5: Elemental Analysis: C, 94.52; H, 5.48 / HRMS [M] &lt; ⁺ & gt ^; : 698

Inv 2-6: Elemental Analysis: C, 94.52; H, 5.48 / HRMS [M] &lt; ⁺ & gt ^; : 698

Inv 2-7: Elemental Analysis: C, 94.27; H, 5.73 / HRMS [M] &lt; ⁺ & gt ^; : 738

Inv 2-8: Elemental Analysis: C, 94.85; H, 5.15 / HRMS [M] &lt; ⁺ & gt ^; : 860

Inv 2-9: Elemental Analysis: C, 94.62; H, 5.38 / HRMS [M] &lt; ⁺ & gt ^; : 746

Inv 2-10: Elemental Analysis: C, 94.87; H, 5.13 / HRMS [M] &lt; ⁺ & gt ^; : 746

Inv 2-11: Elemental Analysis: C, 94.94; H, 5.06 / HRMS [M] &lt; ⁺ & gt ^; : 796

Inv 2-12: Elemental Analysis: C, 94.62; H, 5.38 / HRMS [M] &lt; ⁺ & gt ^; : 748

[ Synthetic example  2-17] Compound Inv  Synthesis of 2-13

10 g of 6,11-bis (9,9-dimethyl-9H-fluoren-2-yl) -13,13-dimethyl-13H-indeno [1,2- b] anthracene (EMI6) obtained in Synthesis Example 2-2 (1eq, 0.014mol) and naphthalen-2-ylboronic acid 3.0g ( 1.2eq, 0.016mol), Pd (PPh 3) 4 0.6g into the flask (0.03eq, 5.1mmol) 2M K2CO3 saturated aqueous solution 15ml and 150ml Toluene And the mixture was heated and stirred for 12 hours. After completion of the reaction, the reaction solution was filtered through Celite and then extracted with MC to obtain 9.3 g (yield: 83%) of the final compound Inv 1-21 through column chromatography.

Inv 2-13: Elemental Analysis: C, 93.99; H, 6.01 / HRMS [M] &lt; ⁺ & gt ^; : 804

[Synthesis Examples 2-18 to 2-28] Synthesis of compounds Inv 2-14 to Inv 2-24

Synthesis was carried out using the same method as that of the compound Inv 2-13 of Synthesis Example 2-17, and it was obtained as a pale yellow solid.

Inv 2-14: Elemental Analysis: C, 93.99; H, 6.01 / HRMS [M] &lt; ⁺ & gt ^; : 804

Inv 2-15: Elemental Analysis: C, 94.11; H, 5.89 / HRMS [M] &lt; ⁺ & gt ^; : 854

Inv 2-16: Elemental Analysis: C, 93.94; H, 6.06 / HRMS [M] &lt; ⁺ & gt ^; : 830

Inv 2-17: Elemental Analysis: C, 93.94; H, 6.06 / HRMS [M] &lt; ⁺ & gt ^; : 830

Inv 2-18: Elemental Analysis: C, 93.94; H, 6.06 / HRMS [M] &lt; ⁺ & gt ^; : 830

Inv 2-19: Elemental Analysis: C, 93.75; H, 6.25 / HRMS [M] &lt; ⁺ & gt ^; : 870

Inv 2-20: Elemental Analysis: C, 94.27; H, 5.73 / HRMS [M] &lt; ⁺ & gt ^; : 992

Inv 2-21: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] &lt; ⁺ & gt ^; : 879

Inv 2-22: Elemental Analysis: C, 94.27; H, 5.73 / HRMS [M] &lt; ⁺ & gt ^; : 878

Inv 2-23: Elemental Analysis: C, 94.36; H, 5.64 / HRMS [M] &lt; ⁺ & gt ^; : 928

Inv 2-24: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] &lt; ⁺ & gt ^; : 880

[Synthesis Example 2-29] Synthesis of compound Inv 2-25

(9,9-dimethyl-9H-fluoren-2-yl) -13,13-dimethyl-13H-indeno [1,2-b] anthracene EMI 7) 10g (1eq, 0.014mol ) and naphthalen-2-ylboronic acid 3.0g ( 1.2eq, 0.016mol), Pd (PPh 3) 4 0.6g (0.03eq, 5.1mmol) were placed in the flask 2M K2CO3 saturated aqueous solution And 150 ml of toluene, and the mixture was heated and stirred for 12 hours. After completion of the reaction, the reaction solution was filtered through Celite and then extracted with MC to obtain 9.3 g (yield: 83%) of final compound Inv 2-25 through column chromatography.

Inv 2-25: Elemental Analysis: C, 93.99; H, 6.01 / HRMS [M] &lt; ⁺ & gt ^; : 804

[Synthesis Example 2-30 to Synthesis Example 2-43] Synthesis of compound Inv 2-26 to compound Inv 2-36

Synthesis was carried out using the same method as that for the synthesis of the compound Inv 2-25 of Synthesis Example 2-29, and it was obtained as a pale yellow solid.

Inv 2-26: Elemental Analysis: C, 93.99; H, 6.01 / HRMS [M] &lt; ⁺ & gt ^; : 804

Inv 2-27: Elemental Analysis: C, 94.54; H, 5.46 / HRMS [M] &lt; ⁺ & gt ^; : 774

Inv 2-28: Elemental Analysis: C, 94.36; H, 5.64 / HRMS [M] &lt; ⁺ & gt ^; : 750

Inv 2-29: Elemental Analysis: C, 94.36; H, 5.64 / HRMS [M] &lt; ⁺ & gt ^; : 750

Inv 2-30: Elemental Analysis: C, 94.36; H, 5.64 / HRMS [M] &lt; ⁺ & gt ^; : 750

Inv 2-31: Elemental Analysis: C, 94.14; H, 5.86 / HRMS [M] &lt; ⁺ & gt ^; : 790

Inv 2-32: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] &lt; ⁺ & gt ^; : 912

Inv 2-33: Elemental Analysis: C, 94.46; H, 5.54 / HRMS [M] &lt; ⁺ & gt ^; : 800

Inv 2-34: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] &lt; ⁺ & gt ^; : 799

Inv 2-35: Elemental Analysis: C, 94.78; H, 5.22 / HRMS [M] &lt; ⁺ & gt ^; : 848

Inv 2-36: Elemental Analysis: C, 94.46; H, 5.54 / HRMS [M] &lt; ⁺ & gt ^; : 800

[Synthesis Example 2-41] Synthesis of Compound Inv 2-37

10 g (1 eq, 0.012 mol) of the 9-bromo-6,11-di (13-dimethyl-13H-indeno [1,2- b] anthracene mol) and naphthalen-2-ylboronic acid 2.9g ( 1.2eq, 0.015mol), Pd (PPh 3) 4 0.52g (0.03eq, 4.6mmol) were placed in the flask was dissolved into saturated aqueous 2M K2CO3 and 15ml Toluene 150ml 12 Lt; / RTI &gt; After completion of the reaction, the reaction mixture was filtered through Celite and then extracted with MC to obtain 7.8 g (yield: 80%) of the final compound Inv 2-37 through column chromatography.

Inv 2-37: Elemental Analysis: C, 95.09; H, 4.91 / HRMS [M] &lt; ⁺ & gt ^; : 820

[Synthesis Example 2-42 to Synthesis Example 2-52] Synthesis of Compound Inv 2-38 to Compound Inv 2-48

Synthesis was carried out using the same method as that of the compound Inv 2-37 of Synthesis Example 2-41, and it was obtained as a pale yellow solid.

Inv 2-38: Elemental Analysis: C, 94.78; H, 5.22 / HRMS [M] &lt; ⁺ & gt ^; : 848

Inv 2-39: Elemental Analysis: C, 95.14; H, 4.86 / HRMS [M] &lt; ⁺ & gt ^; : 870

Inv 2-40: Elemental Analysis: C, 95.00; H, 5.00 / HRMS [M] &lt; ⁺ & gt ^; : 846

Inv 2-41: Elemental Analysis: C, 95.00; H, 5.00 / HRMS [M] &lt; ⁺ & gt ^; : 846

Inv 2-42: Elemental Analysis: C, 95.00; H, 5.00 / HRMS [M] &lt; ⁺ & gt ^; : 846

Inv 2-43: Elemental Analysis: C, 94.77; H, 5.23 / HRMS [M] &lt; ⁺ & gt ^; : 886

Inv 2-44: Elemental Analysis: C, 95.00; H, 5.00 / HRMS [M] &lt; ⁺ & gt ^; : 846

Inv 2-45: Elemental Analysis: C, 95.21; H, 4.79 / HRMS [M] &lt; ⁺ & gt ^; : 1008

Inv 2-46: Elemental Analysis: C, 95.06; H, 4.94 / HRMS [M] &lt; ⁺ & gt ^; : 896

Inv 2-47: Elemental Analysis: C, 95.27; H, 4.73 / HRMS [M] &lt; ⁺ & gt ^; : 894

Inv 2-48: Elemental Analysis: C, 95.31; H, 4.69 / HRMS [M] &lt; ⁺ & gt ^; : 944

[Synthesis Example 3-1] Synthesis of intermediate EMI 9

<Step 1> Synthesis of 2- (9,9-dimethyl-9H-fluorene-2-carbonyl) benzoic acid

40 g (1 eq, 0.146 mol) of 9,9-dimethyl-9H-fluorene and 36.5 g (1.1 eq, 0.161 mol) of phthalic anhydride were placed in a reaction vessel and 1.5 liter of dichloromethane was added. 29.2 g (1.5 eq, 0.219 mol) of aluminum chloride was gradually added at 0 ° C, and then the temperature was raised to room temperature, followed by stirring for 12 hours. After the completion of the reaction, distilled water was slowly added to the reaction mixture at 0 ° C, excess dichloromethane was extracted and washed several times with distilled water. After removing the solvent, the resulting solid was placed in a 2-liter Hexane container, washed and then filtered and dried to obtain 59.8 g of 2- (9,9-dimethyl-9H-fluorene-2-carbonyl) benzoic acid in a yield of 82%.

^{1 H-NMR: 8.44 (t} , 2H), 8.23 (d, 1H), 7.96 (m, 5H), 7.72 (m, 5H), 7.55 (t, 1H), 1.67 (s, 6H).

<Step 2> Synthesis of 13,13-dimethyl-6H-indeno [1,2-b] anthracene-6,11 (13H) -dione (EMI9)

20 g (1 eq, 0.0399 mol) of 2- (9,9-dimethyl-9H-fluorene-2-carbonyl) benzoic acid was added to the flask and 50 ml of polyphosphoric acid was added. And the mixture was heated with stirring at 140 DEG C for 2 hours. After cooling to 50 ° C or less, distilled water was slowly added. The resulting solid was filtered and washed with a small amount of methanol and dried to obtain 15 g of 13,13-dimethyl-6H-indeno [1,2-b] anthracene-6,11 (13H) -dione (EMI- 78%).

^{1 H-NMR: 8.29 (t} , 3H), 8.09 (s, 2H), 7.85 (d, 2H), 7.72 (m, 2H), 1.67 (s, 6H).

[Synthesis Example 3-2] Synthesis of intermediate EMI 10

<Step 1> Synthesis of 2- (9,9'-spirobi [fluorene] -2-ylcarbonyl) benzoic acid

10 g (1 eq, 0.06 mol) of spirofluorene and 10.2 g (1.1 eq, 0.069 mol) of phthalic anhydride were placed in a reaction vessel and 1 liter of dichloromethane was added. 13.8 g (1.5 eq, 0.1 mol) of aluminum chloride was gradually added at 0 ° C, and then the temperature was raised to room temperature, followed by stirring for 12 hours. After the completion of the reaction, distilled water was slowly added to the reaction mixture at 0 ° C, excess dichloromethane was extracted and washed several times with distilled water. After removing the solvent, the resulting solid was placed in a 2-liter Hexane container, washed, and then filtered and dried to obtain 22 g of 2- (9,9'-spirobi [fluorene] -2-ylcarbonyl) benzoic acid in a yield of 82%.

^{1 H-NMR: 8.44 (t} , 2H), 8.23 (d, 1H), 7.96 (m, 5H), 7.72 (m, 5H), 7.55 (t, 1H), 1.67 (s, 6H).

<Step 2> Synthesis of spiro [fluorene-9,13'-indeno [1,2-b] anthracene] -6 ', 11'-dione (EMI10)

20 g (1 eq, 0.04 mol) of 2- (9,9'-spirobi [fluorene] -2-ylcarbonyl) benzoic acid were placed in a flask and 50 ml of polyphosphoric acid was added. And the mixture was heated with stirring at 140 DEG C for 2 hours. After cooling to 50 ° C or less, distilled water was slowly added. The resulting solid was filtered and washed with a small amount of methanol and dried to obtain 15 g of spiro [fluorene-9,13'-indeno [1,2-b] anthracene] -6 ', 11'-dione (EMI- = 78%).

^{1 H-NMR: 8.29 (t} , 3H), 8.09 (s, 2H), 7.85 (d, 2H), 7.72 (m, 2H), 1.67 (s, 6H).

[Synthesis Example 3-3] Synthesis of Compound Inv 3-1

2-Bromonaphthrene (5.3 g, 2.2 eq, 0.067 mol) was added to the flask, and 200 ml of THF was added to dissolve the solution. 45.3 ml (2.5 eq, 0.075 mol) of n-BuLi was slowly added dropwise at -78 ° C. 10 g (1 eq, 0.03 mol) of 13,13-dimethyl-13H-indeno [1,2-b] anthracene-6,11-dione (EMI-9) obtained in Synthesis Example 3-1 , And the mixture was stirred at room temperature for 17 hours. After completion of the reaction, the reaction mixture was extracted with washing and ethyl acetate as distilled water, and then subjected to column chromatography to obtain 13,13-dimethyl-6,11-di (naphthalen-2-yl) b] anthracene-6,11-diol (yield = 72%).

5 g (1 eq, 0.0075 mol) of 13,13-dimethyl-6,11-di (naphthalen-2-yl) -11,13-dihydro-6H- indeno [1,2- b] anthracene- 12.45g (10eq, 0.075mol) of potassium iodide and 6g (5eq, 0.037mol) of sodium hypophosphite were placed in a flask, and 200ml of acetic acid was added thereto, followed by heating and stirring for 5 hours. After the reaction, the reaction solution was added to an excess amount of distilled water to form a solid and washed, and then filtered and subjected to column chromatography to obtain the final compound 13,13-dimethyl-6,11-di (naphthalen-2-yl) , 2-b] anthracene (yield = 76%).

Inv 3-1: Elemental Analysis: C, 94.47; H, 5.53 / HRMS [M] &lt; ⁺ & gt ^; : 546

[Synthesis Example 3-4 to Synthesis Example 3-31] Synthesis of Compound Inv 3-2 to Compound Inv 3-29

It was synthesized using the same method as the method for synthesis of compound Inv 3-1 of Synthesis Example 3-3, and it was obtained as a pale yellow solid.

Inv 3-2: Elemental Analysis: C, 94.28; H, 5.72 / HRMS [M] &lt; ⁺ & gt ^; : 598

Inv 3-3: Elemental Analysis: C, 94.28; H, 5.72 / HRMS [M] &lt; ⁺ & gt ^; : 678

Inv 3-4: Elemental Analysis: C, 94.28; H, 5.72 / HRMS [M] &lt; ⁺ & gt ^; : 598

Inv 3-5: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] &lt; ⁺ & gt ^; : 646

Inv 3-6: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] &lt; ⁺ & gt ^; : 646

Inv 3-7: Elemental Analysis: C, 94.52; H, 5.48 / HRMS [M] &lt; ⁺ & gt ^; : 698

Inv 3-8: Elemental Analysis: C, 94.47; H, 5.53 / HRMS [M] &lt; ⁺ & gt ^; : 546

Inv 3-9: Elemental Analysis: C, 95.07; H, 4.93 / HRMS [M] &lt; ⁺ & gt ^; : 694

Inv 3-10: Elemental Analysis: C, 94.52; H, 5.48 / HRMS [M] &lt; ⁺ & gt ^; : 698

Inv 3-11: Elemental Analysis: C, 95.18; H, 4.82 / HRMS [M] &lt; ⁺ & gt ^; : 794

Inv 3-12: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] &lt; ⁺ & gt ^; : 646

Inv 3-13: Elemental Analysis: C, 94.36; H, 5.64 / HRMS [M] &lt; ⁺ & gt ^; : 750

Inv 3-14: Elemental Analysis: C, 94.98; H, 5.02 / HRMS [M] &lt; ⁺ & gt ^; : 922

Inv 3-15: Elemental Analysis: C, 95.18; H, 4.82 / HRMS [M] &lt; ⁺ & gt ^; : 668

Inv 3-16: Elemental Analysis: C, 94.97; H, 5.03 / HRMS [M] &lt; ⁺ & gt ^; : 720

Inv 3-17: Elemental Analysis: C, 94.46; H, 5.54 / HRMS [M] &lt; ⁺ & gt ^; : 800

Inv 3-18: Elemental Analysis: C, 94.97; H, 5.03 / HRMS [M] &lt; ⁺ & gt ^; : 720

Inv 3-19: Elemental Analysis: C, 95.28; H, 4.72 / HRMS [M] &lt; ⁺ & gt ^; : 768

Inv 3-20: Elemental Analysis: C, 95.07; H, 4.93 / HRMS [M] &lt; ⁺ & gt ^; : 694

Inv 3-21: Elemental Analysis: C, 94.52; H, 5.48 / HRMS [M] &lt; ⁺ & gt ^; : 698

Inv 3-22: Elemental Analysis: C, 95.18; H, 4.82 / HRMS [M] &lt; ⁺ & gt ^; : 794

Inv 3-23: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] &lt; ⁺ & gt ^; : 646

Inv 3-24: Elemental Analysis: C, 94.36; H, 5.64 / HRMS [M] &lt; ⁺ & gt ^; : 750

Inv 3-25: Elemental Analysis: C, 94.98; H, 5.02 / HRMS [M] &lt; ⁺ & gt ^; : 922

Inv 3-26: Elemental Analysis: C, 95.18; H, 4.82 / HRMS [M] &lt; ⁺ & gt ^; : 668

Inv 3-27: Elemental Analysis: C, 94.97; H, 5.03 / HRMS [M] &lt; ⁺ & gt ^; : 720

Inv 3-28: Elemental Analysis: C, 94.46; H, 5.54 / HRMS [M] &lt; ⁺ & gt ^; : 800

Inv 3-29: Elemental Analysis: C, 94.97; H, 5.03 / HRMS [M] &lt; ⁺ & gt ^; : 720

[Synthesis Example 4-1] Synthesis of intermediate EMI 11

Synthesis of 4-bromo-2- (7-bromo-9,9-dimethyl-9H-fluorene-2-carbonyl) -benzoic acid

40 g (1 eq, 0.146 mol) of 2-bromo-9,9-dimethyl-9H-fluorene and 36.5 g (1.1 eq, 0.161 mol) of 2-bromo phthalic anhydride were placed in a reaction vessel and 1.5 liter of dichloromethane was added. 29.2 g (1.5 eq, 0.219 mol) of aluminum chloride was gradually added at 0 ° C, and then the temperature was raised to room temperature, followed by stirring for 12 hours. After the completion of the reaction, distilled water was slowly added to the reaction mixture at 0 ° C, excess dichloromethane was extracted and washed several times with distilled water. After removing the solvent, the resulting solid was washed in a Hexane 2 liter container and then filtered and dried to obtain 59.8 g of 4-bromo-2- (7-bromo-9,9-dimethyl-9H-fluorene-2-carbonyl) 82%.

^{1 H-NMR: 8.44 (t} , 1H), 8.23 (d, 1H), 7.96 (m, 5H), 7.72 (m, 5H), 7.55 (t, 1H), 1.67 (s, 6H).

Step 2 Synthesis of 2,9-dibromo-13,13-dimethyl-6H-indeno [1,2-b] anthracene-6,11 (13H)

Polyphosphoric acid (50 ml) was added to 20 g (1 eq, 0.0399 mol) of 4-bromo-2- (7-bromo-9,9-dimethyl-9H-fluorene-2-carbonyl) -benzoic acid. And the mixture was heated with stirring at 140 DEG C for 2 hours. After cooling to 50 ° C or less, distilled water was slowly added. The resulting solid was filtered and washed with a small amount of methanol and dried to obtain 15 g of 2,9-dibromo-13,13-dimethyl-6H-indeno [1,2-b] anthracene-6,11 (13H) = 78%).

^{1 H-NMR: 8.29 (t} , 2H), 8.09 (s, 2H), 7.85 (d, 2H), 7.72 (m, 2H), 1.67 (s, 6H).

<Step 3> Synthesis of 2,9-dibromo-13,13-dimethyl-11,13-dihydro-6H-indeno [1,2- b] anthracene-6,11-diol

20 g (1 eq, 0.041 mol) of 2,9-dibromo-13,13-dimethyl-6H-indeno [1,2- b] anthracene-6,11 (13H) -dione was placed in a flask and 150 ml of MeOH was added. 6.2 g (4 eq, 0.164 mol) of sodium borohydride was added slowly at 0 ° C. After stirring for 5 hours, add ice-water slowly. MC and then Hex recrystallized to obtain 15 g (yield: 78%) of 2,9-dibromo-13,13-dimethyl-11,13-dihydro-6H- indeno [1,2- b] anthracene-6,11- .

HRMS [M] ⁺ : calcd 486.6, found 485.97.

Step 4 Synthesis of 2,9-dibromo-13,13-dimethyl-6H-indeno [1,2-b] anthracen-11 (13H)

(1 eq, 0.003 mol) of 2,9-dibromo-13,13-dimethyl-11,13-dihydro-6H-indeno [1,2- b] anthracene-6,11-diol and 100 ml of 5N HCl . After stirring for 5 hours, the resulting solid was filtered and washed several times with distilled water. And dried naturally to obtain 13.2 g (yield: 92%) of 2,9-dibromo-13,13-dimethyl-6H-indeno [1,2- b] anthracen-11 (13H) -one.

HRMS [M] ⁺ : calcd 468.18, found 465.9

Step 5 Synthesis of 2,9-dibromo-13,13-dimethyl-13H-indeno [1,2-b] anthracene (EMI11)

13 g (1 eq, 0.027 mol) of 2,9-dibromo-13,13-dimethyl-6H-indeno [1,2- b] anthracen-11 (13H) -one were placed in a flask and 200 ml of IPA was added. 3.1 g (3 eq, 0.081 mol) of sodium borohydride was slowly added at 0 ° C, and the mixture was heated and stirred at 100 ° C. After stirring for 24 to 36 hours, the mixture was cooled to room temperature and then ice-water was slowly added thereto. The resulting solid was filtered, washed several times with distilled water, and then dried. 8.5 g (yield: 70%) of 2,9-dibromo-13,13-dimethyl-13H-indeno [l, 2-b] anthracene (EMI11) was obtained through column chromatography.

HRMS [M] &lt; ⁺ &gt;: calcd 452.1 found 449.9.

[Synthesis Example 4-2] Synthesis of intermediate EMI12

Synthesis of 2,9-dibromo-6,11,13,13-tetramethyl-11,13-dihydro-6H-indeno [1,2-b] anthracene-6,11-diol

(1 eq, 0.02 mol), and 200 ml of THF was added to the flask. The flask was charged with 10 g (1 eq, 0.02 mol) of 2,9-dibromo-13,13-dimethyl-6H- indeno [1,2- b] anthracene-6,11 1 g (2.2 eq, 0.045 mol) of methyllithium was slowly added at 0 ° C, and the mixture was heated and stirred at 60 ° C. After stirring for 12 hours, the mixture was cooled to room temperature, and then ice-water was slowly added thereto. MC and then rinsed several times with distilled water. After removing the solvent, 2.5 g of 2,9-dibromo-6,11,13,13-tetramethyl-11,13-dihydro-6H-indeno [1,2-b] anthracene-6,11- Yield = 25%).

Elemental Analysis: C, 58.39; H, 4.31; Br, 31.08, 0. 6.22 / HRMS [M] &lt; ⁺ & gt ^; : 514.

<Step 2> Synthesis of 2,9-dibromo-6,11,13,13-tetramethyl-13H-indeno [1,2-b] anthracene (EMI12)

2.5 g of 2,9-dibromo-6,11,13,13-tetramethyl-11,13-dihydro-6H-indeno [1,2-b] anthracene-6,11- 4], 2,9-dibromo-6,11,13,13-tetramethyl-13H-indeno [1,2-b] anthracene (EMI12) was obtained.

Elemental Analysis: C, 62.53; H, 4.20; Br, 33.28 / HRMS [M] &lt; ⁺ & gt ^; : 477.

[Synthesis Example 4-3] Synthesis of intermediate EMI 13

Step 1: Preparation of 2,9-dibromo-6,11-di-tert-butyl-13,13-dimethyl-11,13-dihydro-6H- indeno [1,2- b] anthracene-6,11-diol synthesis

Di-tert-butyl-13,13-dimethyl-11,13-dihydro-6H-indeno [1, 2-b] anthracene-6,11-diol (yield = 20%).

Elemental Analysis: C, 62.22; H, 5.73; Br, 27.71; O, 5.35 / HRMS [M] &lt; ⁺ & gt ^; : 598.

<Step 2> Synthesis of 2,9-dibromo-6,11,13,13-tetramethyl-13H-indeno [1,2-b] anthracene (EMI13)

2 g (yield = 77%) of 2,9-dibromo-6,11,13,13-tetramethyl-13H-indeno [1,2- b] anthracene was obtained in the same manner as in <Step 2> ).

Elemental Analysis: C, 65.97; H, 5.71; Br, 28.31 / HRMS [M] &lt; ⁺ & gt ^; : 564.

[Synthesis Example 4-4] Synthesis of Compound Inv 4-1

10 g (1 eq, 0.022 mol) of 2,9-dibromo-13,13-dimethyl-13H-indeno [1,2-b] anthracene (EMI11) obtained in Synthetic Example 4-1 and 6.2 g of naphthalen- (2.2 eq, 0.048 mol) and 0.76 g (0.03 eq, 6.61 mmol) of Pd (PPh ₃ ) ₄ were placed in a flask, and 20 ml of a saturated aqueous solution of 2M K ₂ CO ₃ and 300 ml of toluene were added and dissolved. After completion of the reaction, the reaction solution was filtered through Celite and then extracted with MC to obtain 9.96 g (yield: 83%) of final compound Inv 4-1 by column chromatography.

Inv 4-1: Elemental Analysis: C, 94.47; H, 5.53 / HRMS [M] &lt; ⁺ & gt ^; : 546

[Synthesis Example 4-5 to Synthesis Example 4-33] Synthesis of compound Inv 4-2 to compound Inv 4-30

Synthesis was carried out using the same method as that of the compound Inv 4-1 of Synthesis Example 4-4, and it was obtained as a pale yellow solid.

Inv 4-2: Elemental Analysis: C, 94.47; H, 5.53 / HRMS [M] &lt; ⁺ & gt ^; : 546

Inv 4-3: Elemental Analysis: C, 94.79; H, 5.21 / HRMS [M] &lt; ⁺ & gt ^; : 696

Inv 4-4: Elemental Analysis: C, 94.28; H, 5.72 / HRMS [M] &lt; ⁺ & gt ^; : 698

Inv 4-5: Elemental Analysis: C, 94.28; H, 5.72 / HRMS [M] &lt; ⁺ & gt ^; : 698

Inv 4-6: Elemental Analysis: C, 94.36; H, 5.64 / HRMS [M] &lt; ⁺ & gt ^; : 750

Inv 4-7: Elemental Analysis: C, 94.52; H, 5.48 / HRMS [M] &lt; ⁺ & gt ^; : 698

Inv 4-8: Elemental Analysis: C, 95.07; H, 4.93 / HRMS [M] &lt; ⁺ & gt ^; : 694

Inv 4-9: Elemental Analysis: C, 93.76; H, 6.24 / HRMS [M] &lt; ⁺ & gt ^; : 678

Inv 4-10: Elemental Analysis: C, 94.98; H, 5.02 / HRMS [M] &lt; ⁺ & gt ^; : 923

Inv 4-11: Elemental Analysis: C, 94.04; H, 5.96 / HRMS [M] &lt; ⁺ &gt;: 574

Inv 4-12: Elemental Analysis: C, 94.04; H, 5.96 / HRMS [M] &lt; ⁺ &gt;: 574

Inv 4-13: Elemental Analysis: C, 94.44; H, 5.56 / HRMS [M] &lt; ⁺ & gt ^; : 724

Inv 4-14: Elemental Analysis: C, 93.89; H, 6.11 / HRMS [M] &lt; ⁺ & gt ^; : 626

Inv 4-15: Elemental Analysis: C, 93.89; H, 6.11 / HRMS [M] &lt; ⁺ & gt ^; : 626

Inv 4-16: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] &lt; ⁺ & gt ^; : 778

Inv 4-17: Elemental Analysis: C, 94.18; H, 5.82 / HRMS [M] &lt; ⁺ & gt ^; : 726

Inv 4-18: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] &lt; ⁺ & gt ^; : 722

Inv 4-19: Elemental Analysis: C, 93.44; H, 6.56 / HRMS [M] &lt; ⁺ & gt ^; : 706

Inv 4-20: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] &lt; ⁺ & gt ^; : 951

Inv 4-21: Elemental Analysis: C, 94.36; H, 5.64 / HRMS [M] &lt; ⁺ & gt ^; : 750

Inv 4-22: Elemental Analysis: C, 94.52; H, 5.48 / HRMS [M] &lt; ⁺ & gt ^; : 698

Inv 4-23: Elemental Analysis: C, 95.07; H, 4.93 / HRMS [M] &lt; ⁺ & gt ^; : 694

Inv 4-24: Elemental Analysis: C, 93.76; H, 6.24 / HRMS [M] &lt; ⁺ & gt ^; : 678

Inv 4-25: Elemental Analysis: C, 94.98; H, 5.02 / HRMS [M] &lt; ⁺ & gt ^; : 923

Inv 4-26: Elemental Analysis: C, 94.04; H, 5.96 / HRMS [M] &lt; ⁺ &gt;: 574

Inv 4-27: Elemental Analysis: C, 94.04; H, 5.96 / HRMS [M] &lt; ⁺ &gt;: 574

Inv 4-28: Elemental Analysis: C, 94.44; H, 5.56 / HRMS [M] &lt; ⁺ & gt ^; : 724

Inv 4-29: Elemental Analysis: C, 93.89; H, 6.11 / HRMS [M] &lt; ⁺ & gt ^; : 626

Inv 4-30: Elemental Analysis: C, 93.89; H, 6.11 / HRMS [M] &lt; ⁺ & gt ^; : 626

[Synthesis Example 5-1] Synthesis of intermediate EMI14

<Step 1> Synthesis of 2,2'-dibromobiphenyl

1,2-dibromobenzene 10 g (1 eq, 0.042 mol) was placed in a flask and 150 ml of THF was added. After slowly adding 14.2 ml (0.5 eq, 0.021 mol) of n-buthyllithium at -78 ° C, the temperature was raised to room temperature. After stirring for 1 hour, distilled water was added and stirred for 1 minute. After extracting hexane and removing the solvent, 5 g (yield: 65%) of 2,2'-dibromobiphenyl was obtained by column chromatography.

Elemental Analysis: C, 46.20; H, 2.58; Br, 51.22 / HRMS [M] &lt; ⁺ & gt ^; : 312.

<Step 2> Synthesis of 5,5-dimethyl-5H-dibenzo [b, d] silole

1,2-dibromobiphenyl were placed in a 10 g (1 eq, 0.032 mol) flask and 150 ml of THF was added. Add slowly 24.1 ml (1.2eq, 0.038mol) of n-buthyllithium at -78 ° C, stir for 30 minutes and add 4.1g (1.2eq, 0.038mol) of chlorotrimethylsilane. After stirring for 4 hours, distilled water was added and stirred for about 10 minutes. After extraction with hexane and solvent removal, 5.17 g (yield = 77%) of 5,5-dimethyl-5H-dibenzo [b, d] silole was obtained by column chromatography.

Elemental Analysis: C, 79.94; H, 6.71; Si, 13.35 / HRMS [M] &lt; ⁺ & gt ^; : 210.

Synthesis of 4-bromo-2- (5,5-dimethyl-5H-dibenzo [b, d] silole-3-carbonyl) benzoic acid

5 g (1 eq, 0.023 mol) of 5,5-dimethyl-5H-dibenzo [b, d] silole and 5.7 g (1.1 eq, 0.025 mol) of 2-bromo phthalic anhydride were placed in a flask and 200 ml of dichloromethane was added. 4.5 g (1.5 eq, 0.0345 mol) of aluminum chloride was gradually added at 0 ° C, then the temperature was raised to room temperature, and the mixture was stirred for 12 hours. After the completion of the reaction, distilled water was slowly added to the reaction mixture at 0 ° C, excess dichloromethane was extracted and washed several times with distilled water. After removing the solvent, the resulting solid was placed in a 500 ml Hexane container, washed, and then filtered and dried to obtain 6.5 g of 4-bromo-2- (5,5-dimethyl-5H-dibenzo [b, d] silole-3-carbonyl) benzoic acid (Yield = 65%).

Elemental Analysis: C, 60.42; H, 3.92; Br, 18.27; O, 10.97; Si, 6.42

HRMS [M] &lt; ⁺ & gt ^; : 436.

Synthesis of 9-bromo-5,5-dimethyl-5H-anthra [2,3-b] benzo [d] silole-7,12-dione (EMI14)

5 g (1 eq, 0.011 mol) of 4-bromo-2- (5,5-dimethyl-5H-dibenzo [b, d] silole-3-carbonyl) benzoic acid and 50 ml of polyphosphoric acid were added. And the mixture was heated with stirring at 140 DEG C for 2 hours. After cooling to 50 ° C or less, distilled water was slowly added. The resulting solid was filtered and washed with a small amount of methanol and dried to obtain 9-bromo-5,5-dimethyl-5H-anthra [2,3-b] benzo [d] silole-7,12- 4.5 g (Yield = 72%) was obtained.

Elemental Analysis: C, 63.01; H, 3.61; Br, 19.05; O, 7.63; Si, 6.70

HRMS [M] &lt; ⁺ & gt ^; : 418

[Synthesis Example 5-2] Synthesis of Compound Inv 5-1

3.2 g (1.2 eq, 0.019 mol) of naphthalen-2-ylboronic acid and 0.65 g (0.03 eq, 5.7 mmol) of Pd (PPh3) _{4 were added to a} mixture of ₁₀ g (1 eq, 0.016 mol) of EM- 15 ml of 2M K ₂ CO ₃ saturated aqueous solution and 150 ml of toluene were added to the flask, and the mixture was heated and stirred for 12 hours. After completion of the reaction, the reaction solution was filtered through Celite and then extracted with MC to obtain final compound Inv 5-1 (13,13-dimethyl-6,9,11-tri (naphthalen-2-yl) 13H-indeno [1,2-b] anthracene (yield: 88.7%).

Inv 5-1: Elemental Analysis: C, 94.61; H, 5.39 / HRMS [M] &lt; ⁺ & gt ^; : 672.

[Synthesis Example 5-3 to Synthesis Example 5-48] Synthesis of Compound Inv 5-2 to Compound Inv 5-47

Synthesis was carried out using the same method as that of the compound Inv 5-1 of Synthesis Example 5-2, and it was obtained as a pale yellow solid.

Inv 5-2: Elemental Analysis: C, 94.61; H, 5.39 / HRMS [M] &lt; ⁺ & gt ^; : 672.

Inv 5-3: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] &lt; ⁺ & gt ^; : 772

Inv 5-4: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] &lt; ⁺ & gt ^; : 722

Inv 5-5: Elemental Analysis: C, 94.52; H, 5.48 / HRMS [M] &lt; ⁺ & gt ^; : 698

Inv 5-6: Elemental Analysis: C, 94.52; H, 5.48 / HRMS [M] &lt; ⁺ & gt ^; : 698

Inv 5-7: Elemental Analysis: C, 94.52; H, 5.48 / HRMS [M] &lt; ⁺ & gt ^; : 698

Inv 5-8: Elemental Analysis: C, 94.27; H, 5.73 / HRMS [M] &lt; ⁺ & gt ^; : 738

Inv 5-9: Elemental Analysis: C, 94.85; H, 5.15 / HRMS [M] &lt; ⁺ & gt ^; : 860

Inv 5-10: Elemental Analysis: C, 94.62; H, 5.38 / HRMS [M] &lt; ⁺ & gt ^; : 748

Inv 5-11: Elemental Analysis: C, 94.62; H, 5.38 / HRMS [M] &lt; ⁺ & gt ^; : 748

Inv 5-12: Elemental Analysis: C, 94.62; H, 5.38 / HRMS [M] &lt; ⁺ & gt ^; : 748

Inv 5-13: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] &lt; ⁺ & gt ^; : 798

Inv 5-14: Elemental Analysis: C, 94.78; H, 5.22 / HRMS [M] &lt; ⁺ & gt ^; : 848

Inv 5-15: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] &lt; ⁺ & gt ^; : 799

Inv 5-16: Elemental Analysis: C, 94.62; H, 5.38 / HRMS [M] &lt; ⁺ & gt ^; : 748

Inv 5-17: Elemental Analysis: C, 94.87; H, 5.13 / HRMS [M] &lt; ⁺ & gt ^; : 746

Inv 5-18: Elemental Analysis: C, 94.94; H, 5.06 / HRMS [M] &lt; ⁺ & gt ^; : 796

Inv 5-19: Elemental Analysis: C, 94.62; H, 5.38 / HRMS [M] &lt; ⁺ & gt ^; : 748

Inv 5-20: Elemental Analysis: C, 94.62; H, 5.38 / HRMS [M] &lt; ⁺ & gt ^; : 748

Inv 5-21: Elemental Analysis: C, 93.99; H, 6.01 / HRMS [M] &lt; ⁺ & gt ^; : 804

Inv 5-22: Elemental Analysis: C, 93.99; H, 6.01 / HRMS [M] &lt; ⁺ & gt ^; : 804

Inv 5-23: Elemental Analysis: C, 94.11; H, 5.89 / HRMS [M] &lt; ⁺ & gt ^; : 854

Inv 5-24: Elemental Analysis: C, 94.11; H, 5.89 / HRMS [M] &lt; ⁺ & gt ^; : 854

Inv 5-25: Elemental Analysis: C, 93.94; H, 6.06 / HRMS [M] &lt; ⁺ & gt ^; : 830

Inv 5-26: Elemental Analysis: C, 93.94; H, 6.06 / HRMS [M] &lt; ⁺ & gt ^; : 830

Inv 5-27: Elemental Analysis: C, 93.94; H, 6.06 / HRMS [M] &lt; ⁺ & gt ^; : 830

Inv 5-28: Elemental Analysis: C, 93.75; H, 6.25 / HRMS [M] &lt; ⁺ & gt ^; : 870

Inv 5-29: Elemental Analysis: C, 94.32; H, 5.68 / HRMS [M] &lt; ⁺ & gt ^; : 992

Inv 5-30: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] &lt; ⁺ & gt ^; : 880

Inv 5-31: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] &lt; ⁺ & gt ^; : 880

Inv 5-32: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] &lt; ⁺ & gt ^; : 880

Inv 5-33: Elemental Analysis: C, 94.16; H, 5.84 / HRMS [M] &lt; ⁺ & gt ^; : 930

Inv 5-34: Elemental Analysis: C, 94.25; H, 5.75 / HRMS [M] &lt; ⁺ & gt ^; : 980

Inv 5-35: Elemental Analysis: C, 94.16; H, 5.84 / HRMS [M] &lt; ⁺ & gt ^; : 930

Inv 5-36: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] &lt; ⁺ & gt ^; : 880

Inv 5-37: Elemental Analysis: C, 94.27; H, 5.73 / HRMS [M] &lt; ⁺ & gt ^; : 878

Inv 5-38: Elemental Analysis: C, 94.36; H, 5.64 / HRMS [M] &lt; ⁺ & gt ^; : 928

Inv 5-39: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] &lt; ⁺ & gt ^; : 880

Inv 5-40: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] &lt; ⁺ & gt ^; : 880

Inv 5-41: Elemental Analysis: C, 94.05; H, 5.95 / HRMS [M] &lt; ⁺ & gt ^; : 880

Inv 5-42: Elemental Analysis: C, 93.99; H, 6.01 / HRMS [M] &lt; ⁺ & gt ^; : 804

Inv 5-43: Elemental Analysis: C, 94.54; H, 5.46 / HRMS [M] &lt; ⁺ & gt ^; : 774

Inv 5-44: Elemental Analysis: C, 94.36; H, 5.64 / HRMS [M] &lt; ⁺ & gt ^; : 750

Inv 5-45: Elemental Analysis: C, 94.14; H, 5.86 / HRMS [M] &lt; ⁺ & gt ^; : 790

Inv 5-46: Elemental Analysis: C, 94.36; H, 5.64 / HRMS [M] &lt; ⁺ & gt ^; : 750

Inv 5-47: Elemental Analysis: C, 94.70; H, 5.30 / HRMS [M] &lt; ⁺ & gt ^; : 912

[Example 1-1] Preparation of ink composition 1-1

0.1 g of the compound Inv 1-1 synthesized in Synthesis Example 1-5 was dissolved in 65.85 g of tetrahydrofuran as the first organic solvent, 0.05 g of DS-Dopant was added thereto and dissolved, and 66 g of a solution was prepared . 22.6 g of N-methylpyrrolidone and 11.39 g of ethylcarbitol acetate were mixed as a second organic solvent, and the mixture was stirred for 10 minutes. Surfynol 61 (Airproduct) and EFKA 3277 (Ciba) were added thereto as additives. A small amount (about 0.001 to 0.01 g) equivalent to a drop was added to prepare 2 34 g of a solution. The prepared solution 1 (66 g) and the solution 2 (34 g) were mixed and stirred to prepare an ink composition 1-1.

[Examples 1-2 to 1-20] Preparation of ink compositions 1-2 to 1-20

Except for using the compounds Inv 1-2 to Inv 1-20 synthesized in Synthesis Examples 1-6 to 1-24 instead of the compound Inv 1-1 used in Example 1-1, To prepare Ink compositions 1-2 to 1-20.

[Example 1-21] Preparation of ink composition 1-21

0.1 g of the compound Inv 1-21 synthesized in Synthesis Example 1-25 was dissolved in 65.85 g of tetrahydrofuran as the first organic solvent and then 0.05 g of DS-Dopant was added thereto and dissolved to prepare 66 g of a solution . As the second organic solvent, 22.6 g of pyrrolidine and 11.39 g of ethyl cellosolve were mixed and stirred for 10 minutes. Surfynol 61 (Airproduct) and EFKA 3277 (Ciba) were added to the mixture as additives. A small amount (about 0.001 to 0.01 g) was added to prepare 2 34 g of a solution. The prepared solution 1 (66 g) and the solution 2 (34 g) were mixed and stirred to prepare an ink composition 1-21.

[Examples 1-22 to 1-40] Preparation of ink compositions 1-22 to 1-40

Except that the compounds Inv 1-22 to Inv 1-40 synthesized in Synthesis Examples 1-26 to 1-44 were used instead of the compound Inv 1-21 used in Example 1-21, To prepare Ink Compositions 1-22 to 1-40.

[Example 1-41] Preparation of ink composition 1-41

0.1 g of the compound Inv 1-41 synthesized in Synthesis Example 1-45 was dissolved in 65.85 g of morpholine as the first organic solvent, and then 0.05 g of DS-Dopant was added thereto and dissolved to prepare 66 g of a solution. As the second organic solvent, 22.6 g of picoline and 11.39 g of hexylmethylketone were mixed and stirred for 10 minutes. Then, EFKA 3772 (Ciba) and BYKETOL-Special (BYK) A small amount (about 0.001 to 0.01 g) was added to prepare 2 34 g of a solution. The prepared solution 1 (66 g) and the solution 2 (34 g) were mixed and stirred to prepare an ink composition 1-41.

[Examples 1-42 to 1-50] Preparation of ink compositions 1-42 to 1-50

Except for using the compounds Inv 1-42 to Inv 1-50 synthesized respectively in Synthesis Examples 1-46 to 1-54 instead of the compound Inv 1-41 used in Example 1-41, To prepare Ink Compositions 1-42 to 1-50.

[Example 1-51] Preparation of ink composition 1-51

0.1 g of the compound Inv 1-51 synthesized in Synthesis Example 1-55 was dissolved in 65.85 g of thiophene, which is the first organic solvent, and 0.05 g of DS-Dopant was added thereto and dissolved to prepare 66 g of a solution. 22.6 g of anisole and 11.39 g of methylcyclohexane were mixed as a second organic solvent, and the mixture was stirred for 10 minutes. Then, EFKA 3772 (Ciba) and BYKETOL-Special (BYK) A small amount (about 0.001 to 0.01 g) was added to prepare 2 34 g of a solution. The prepared solution 1 (66 g) and the solution 2 (34 g) were mixed and stirred to prepare an ink composition 1-51.

[Examples 1-52 to 1-60] Preparation of ink compositions 1-52 to 1-60

Except that the compounds Inv 1-52 to Inv 1-60 respectively synthesized in Synthesis Examples 1-56 to 1-64 were used instead of the compounds Inv 1-51 used in Examples 1-51, To prepare Ink Compositions 1-52 to 1-60.

[Example 2-1] Preparation of ink composition 2-1

0.1 g of the compound Inv 2-1 synthesized in Synthesis Example 2-5 was dissolved in 65.85 g of tetrahydrofuran as the first organic solvent, and then 0.05 g of DS-Dopant was added thereto and dissolved to prepare 66 g of a solution . As the second organic solvent, 22.6 g of pyrrolidine and 11.39 g of butyl cellosolve were mixed and stirred for 10 minutes. Surfynol 61 (Airproduct) and EFKA 3277 (Ciba) were added to the mixture as an additive. A small amount (about 0.001 to 0.01 g) was added to prepare 2 34 g of a solution. The prepared solution 1 (66 g) and the solution 2 (34 g) were mixed and stirred to prepare an ink composition 2-1.

[Examples 2-2 to 2-12] Preparation of Ink Compositions 2-1 to 2-12

Except for using the compounds Inv 2-2 to Inv 2-12 synthesized in Synthesis Examples 2-6 to 2-16 instead of the compound Inv 2-1 used in Example 2-1, To prepare Ink Compositions 2-1 to 2-12.

[Example 2-13] Preparation of Ink Composition 2-13

0.1 g of the compound Inv 2-13 synthesized in Synthesis Example 2-17 was dissolved in 65.85 g of tetrahydrothiophene as the first organic solvent, and then 0.05 g of DS-Dopant was added and dissolved to prepare 66 g of a solution Respectively. 22.6 g of N, N-dimethylacetamide and 11.39 g of ethylbenzene were mixed as the second organic solvent, and the mixture was stirred for 10 minutes. Then, EFKA 3772 (Ciba) and BYKETOL-Special (BYK) A small amount (about 0.001 to 0.01 g) equivalent to a drop was added to prepare 2 34 g of a solution. The prepared solution 1 (66 g) and the solution 2 (34 g) were mixed and stirred to prepare an ink composition 2-13.

[Examples 2-14 to 2-24] Preparation of ink compositions 2-14 to 2-24

Except for using the compounds Inv 2-14 to Inv 2-24 synthesized in Synthesis Examples 2-18 to 2-28 instead of the compound Inv 2-13 used in Examples 2-13, The ink compositions 2-14 to 2-24 were prepared.

[Example 2-25] Preparation of ink composition 2-25

0.1 g of the compound Inv 2-25 synthesized in Synthesis Example 2-29 was dissolved in 65.85 g of pyrrolidine as the first organic solvent and then 0.05 g of DS-Dopant was added thereto and dissolved to prepare 66 g of a solution . 22.6 g of 2-hexanone as the second organic solvent and 11.39 g of 1-tetralone as an aromatic ketone solvent were mixed and stirred for 10 minutes. Then, EFKA 3772 (Ciba) and BYKETOL-Special (BYK Co., Ltd.) were added in a small amount (about 0.001 to 0.01 g) corresponding to one drop to prepare 34 g of a solution. The prepared solution 1 (66 g) and the solution 2 (34 g) were mixed and stirred to prepare an ink composition 2-25.

[Examples 2-26 to 2-36] Preparation of ink compositions 2-26 to 2-36

Except for using the compounds Inv 2-26 to Inv 2-36 synthesized in Synthesis Examples 2-30 to 2-40 instead of the compound Inv 2-25 used in Example 2-25, To prepare Ink Compositions 2-26 through 2-36.

[Example 2-37] Preparation of ink composition 2-37

0.1 g of Compound Inv 2-37 synthesized in Synthesis Example 2-41 was dissolved in 65.85 g of pyran, which is the first organic solvent, and 0.05 g of DS-Dopant was added thereto and dissolved to prepare 66 g of a solution. 22.6 g of 2-pentanone as the second organic solvent and 11.39 g of 2-tetralone as an aromatic ketone solvent were mixed and stirred for 10 minutes. Then, EFKA 3772 (Ciba) and BYKETOL-Special (BYK Co., Ltd.) were added in a small amount (about 0.001 to 0.01 g) corresponding to one drop to prepare 34 g of a solution. The prepared solution 1 (66 g) and the solution 2 (34 g) were mixed and stirred to prepare an ink composition 2-37.

[Examples 2-38 to 2-48] Preparation of ink compositions 2-38 to 2-48

Except for using the compounds Inv 2-38 to Inv 2-48 synthesized in Synthesis Examples 2-42 to 2-52 instead of the compound Inv 2-37 used in Example 2-37, To prepare ink compositions 2-38 to 2-48.

[Example 3-1] Preparation of ink composition 3-1

0.1 g of the compound Inv 3-1 synthesized in Synthesis Example 3-3 was dissolved in 65.85 g of Techa hydropyran, which was the first organic solvent, and 0.05 g of DS-Dopant was added thereto and dissolved to prepare 66 g of a solution Respectively. As the second organic solvent, 22.6 g of pyrrolidine and 11.39 g of 1-propanol were mixed and stirred for 10 minutes. Surfynol 61 (Airproduct Co.) and EFKA 3277 (Ciba Co.) A small amount (about 0.001 to 0.01 g) was added to prepare 2 34 g of a solution. The prepared solution 1 (66 g) and the solution 2 (34 g) were mixed and stirred to prepare an ink composition 3-1.

[Examples 3-2 to 3-29] Preparation of ink compositions 3-2 to 3-29

Except for using the compounds Inv 3-2 to Inv 3-29 synthesized in Synthesis Examples 3-4 to 3-31 instead of the compound Inv 3-1 used in Example 3-1, To prepare Ink Compositions 3-2 to 3-29.

[Example 4-1] Preparation of ink composition 4-1

0.1 g of the compound Inv 4-1 synthesized in Synthesis Example 4-4 was dissolved in 65.85 g of the first organic solvent TechaHydofuran, 0.05 g of DS-Dopant was added thereto and dissolved, and 66 g of the solution was prepared Respectively. 22.6 g of morpholine as a second organic solvent and 11.39 g of 1-tetralone as an aromatic ketone solvent were mixed and stirred for 10 minutes. Then, EFKA-3772 (manufactured by Ciba) and BYKETOL-Special BYK Co., Ltd.) was added to the solution in an amount of about 0.001 to 0.01 g, respectively, to prepare 2 g of a solution. The prepared solution 1 (66 g) and the solution 2 (34 g) were mixed and stirred to prepare an ink composition 4-1.

[Examples 4-2 to 4-30] Preparation of ink compositions 4-2 to 4-30

Except for using the compounds Inv 4-2 to Inv 4-30 synthesized in Synthesis Examples 4-5 to 4-33 instead of the compound Inv 4-1 used in Example 4-1, To prepare Ink Compositions 4-2 to 4-30.

[Example 5-1] Preparation of ink composition 5-1

0.1 g of the compound Inv 5-1 synthesized in Synthesis Example 5-2 was dissolved in 65.85 g of the first organic solvent Techhidroththiophene, 0.05 g of DS-Dopant was added thereto and dissolved, and 66 g of the solution . 22.6 g of N-methylpyrrolidine and 11.39 g of ethyl cellosolve as a second organic solvent were mixed and stirred for 10 minutes. Surfynol 61 (Airproduct) and EFKA 3277 (Ciba) were added thereto as additives. A small amount (about 0.001 to 0.01 g) equivalent to a drop was added to prepare 2 34 g of a solution. The prepared solution 1 (66 g) and the solution 2 (34 g) were mixed and stirred to prepare an ink composition 5-1.

[Examples 5-2 to 5-47] Preparation of ink compositions 5-2 to 5-47

Except for using the compounds Inv 5-2 to Inv 5-47 synthesized in Synthesis Examples 5-3 to 5-48 instead of the compound Inv 5-1 used in Example 5-1, To prepare Ink Compositions 5-2 to 5-47.

[Manufacturing Example 1] Production of Organic Electroluminescent Device

An organic electroluminescent device was prepared by using the ink composition 1-1 prepared in Example 1-1 in the following manner.

Glass substrate coated with ITO (Indium tin oxide) thin film with thickness of 1500Å was washed with distilled water ultrasonic wave. After the distilled water was washed, the substrate was ultrasonically cleaned with a solvent such as isopropyl alcohol, acetone, or methanol, dried, and transferred to a plasma cleaner. Then, the substrate was cleaned using oxygen plasma for 5 minutes, Respectively.

A hole injection layer was formed by thermally vacuum depositing DS-HIL (Doosan) on the prepared ITO (anode) to a thickness of 800 ANGSTROM. On the hole injection layer, a hole transport material a-NPB (N, N-di (naphthalene-1-yl) -N, Ndiphenylbenzidine) was vacuum-deposited to a thickness of 150 Å to form a hole transport layer. The hole transport layer was packed and transferred to a glove box for a printing process having a spin coater or an ink jet device. Then, in the glove box for printing process, the ink composition 1-1 prepared in Example 1-1 was printed and fired on the hole transport layer using a spin coater or an inkjet printer under the glove box condition for printing process to form a host-dopant-based Thereby forming a light emitting layer. Then, Alq ₃ , which is an electron transporting material, was vacuum deposited on the light emitting layer to a thickness of 250 Å to form an electron transporting layer. Then, LiF as an electron injecting material was deposited to a thickness of 10 Å to form an electron injecting layer. Was vacuum-deposited to a thickness of 2000 A to form a cathode. The structure of the thus fabricated organic electroluminescent device is shown in Table 1 below.

[Production Examples 2 to 213] Preparation of Organic Electroluminescent Device

Except that the ink compositions 1-2 to 5-47 prepared in Examples 1-2 to 5-47 were used in place of the ink composition 1-1 used in forming the light emitting layer in Production Example 1, An organic electroluminescent device was prepared in the same manner. The structure of the thus fabricated organic electroluminescent device is shown in Table 1 below.

[Comparative Example 1] Production of organic electroluminescent device

Instead of forming the light emitting layer using the ink composition 1-1 on the hole transport layer in Production Example 1, Alq ₃ was used as a host material on the hole transport layer and C-545T (10- (2- benzothiazolyl) -1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H- [1] benzopyrano [6,7,8-ij] quinolizin-11- %, And vacuum evaporation was performed to a thickness of 300 ANGSTROM to form a light emitting layer. An organic electroluminescent device was prepared in the same manner as in PREPARATION EXAMPLE 1. The structure of the thus fabricated organic electroluminescent device is shown in Table 1 below.

Hole injection layer (HIL) The hole transport layer (HTL) The organic light emitting layer (EML) Electron transport layer (ETL) The electron injection layer (EIL) cathode
(cathode) Production Examples 1 to 213 DS-HIL a-NPB Ink composition 1-1 to 5-47 Alq ₃ LiF Al Comparative Example 1 DS-HIL a-NPB Alq ₃ + C-545T Alq ₃ LiF Al

[ Experimental Example  One]

The viscosity and the surface tension of the ink compositions 1-1 to 5-47 prepared in Examples 1-1 to 5-47 were measured and the organic electroluminescent devices of Production Examples 1 to 213 were measured at a current density of 10 mA / And the results are shown in Tables 2 to 6, respectively.

Luminescent material Viscosity
(cps) Surface tension
(dyne / cm ² ) Voltage
(V) Current Efficiency
(Cd / A) Ink composition 1-1 3.6 28.2 4.8 10.9 Ink composition 1-2 3.8 28.3 4.2 12.6 Ink composition 1-3 3.8 28.5 3.9 11.9 Ink composition 1-4 3.8 29.0 5.2 12.4 Ink composition 1-5 3.9 28.9 5.2 12.9 Ink composition 1-6 3.6 28.9 4.8 11.2 Ink composition 1-7 3.8 28.9 5.2 11.5 Ink composition 1-8 3.7 29.2 3.9 12.4 Ink composition 1-9 3.7 29.4 4.1 12.8 Ink composition 1-10 3.8 29.4 4.8 12.5 Ink composition 1-11 3.9 29.5 5.2 12.3 Ink composition 1-12 3.9 29.3 5.0 12.8 Ink composition 1-13 3.9 30.1 4.8 11.2 Ink composition 1-14 3.8 28.7 5.2 11.9 Ink composition 1-15 3.9 28.4 4.2 12.9 Ink composition 1-16 3.9 28.4 4.5 11.3 Ink composition 1-17 3.9 30.2 5.2 12.4 Ink composition 1-18 3.9 29.8 4.3 12.2 Ink composition 1-19 3.9 30.1 5.2 12.6 Ink composition 1-20 4.1 30.8 5.3 11.4 Ink composition 1-21 3.4 30.8 4.3 12.2 Ink composition 1-22 3.9 28.9 4.2 12.1 Ink composition 1-23 3.8 31.1 3.9 11.8 Ink composition 1-24 3.8 29.4 4.1 12.5 Ink composition 1-25 3.9 29.4 4.2 12.5 Ink composition 1-26 3.9 29.2 4.5 12.4 Ink composition 1-27 4.2 29.4 4.8 11.2 Ink composition 1-28 3.9 28.9 5.2 11.6 Ink composition 1-29 4.1 29.1 4.2 12.9 Ink composition 1-30 4.0 29.6 4.4 11.2 Ink composition 1-31 4.2 28.4 5.0 12.4 Ink composition 1-32 4.2 29.4 4.8 12.2 Ink composition 1-33 4.5 28.9 5.2 12.4 Ink composition 1-34 3.8 29.2 5.2 11.9 Ink composition 1-35 4.4 29.4 4.3 12.2 Ink composition 1-36 4.8 29.6 4.2 12.6 Ink composition 1-37 4.7 29.6 3.9 11.9 Ink composition 1-38 4.5 29.4 5.2 12.5 Ink composition 1-39 4.6 29.2 5.1 12.9 Ink composition 1-40 4.1 29.4 4.8 11.2 Ink composition 1-41 4.8 29.3 5.2 11.5 Ink composition 1-42 4.8 29.6 4.2 12.9 Ink composition 1-43 5.0 29.4 4.4 11.9 Ink composition 1-44 5.2 29.1 5.2 12.4 Ink composition 1-45 4.9 29.5 4.3 12.2 Ink composition 1-46 5.3 29.2 5.2 12.4 Ink composition 1-47 4.3 29.8 5.2 11.4 Ink composition 1-48 5.1 29.4 4.3 12.2 Ink composition 1-49 4.2 29.2 3.8 13.2 Ink composition 1-50 5.2 29.8 4.2 12.0 Ink composition 1-51 4.6 29.4 4.5 12.3 Ink composition 1-52 5.1 28.9 5.2 12.8 Ink composition 1-53 5.4 29.4 5.1 11.1 Ink composition 1-54 4.8 29.4 4.8 11.9 Ink composition 1-55 5.8 29.5 5.2 12.8 Ink composition 1-56 5.4 30.2 4.2 11.9 Ink composition 1-57 4.8 30.4 4.5 12.4 Ink composition 1-58 5.8 30.4 5.2 12.2 Ink composition 1-59 4.9 30.1 5.1 12.3 Ink composition 1-60 5.8 29.4 4.8 12.5

Luminescent material Viscosity
(cps) Surface tension
(dyne / cm ² ) Voltage
(V) Current Efficiency
(Cd / A) Ink composition 2-1 5.0 29.4 5.7 11.9 Ink composition 2-2 4.8 29.6 5.2 12.4 Ink composition 2-3 4.9 29.5 4.3 12.3 Ink composition 2-4 5.2 29.1 5.2 11.4 Ink composition 2-5 4.3 29.8 4.3 12.9 Ink composition 2-6 5.3 29.2 5.2 12.9 Ink composition 2-7 4.2 29.2 4.2 12.9 Ink composition 2-8 5.1 29.4 4.5 12.9 Ink composition 2-9 4.6 29.4 5.2 12.5 Ink composition 2-10 5.2 29.8 5.1 12.8 Ink composition 2-11 5.4 29.4 4.8 11.2 Ink composition 2-12 5.1 28.9 5.2 11.9 Ink composition 2-13 5.8 29.5 4.2 12.9 Ink composition 2-14 4.8 29.4 4.4 11.9 Ink composition 2-15 4.8 30.4 5.2 12.4 Ink composition 2-16 4.2 29.2 4.3 12.2 Ink composition 2-17 4.9 30.1 5.2 12.4 Ink composition 2-18 4.6 29.4 5.2 11.4 Ink composition 2-19 4.2 29.4 4.3 12.2 Ink composition 2-20 4.8 29.3 4.2 12.1 Ink composition 2-21 4.1 29.1 3.9 11.9 Ink composition 2-22 5.0 29.4 3.7 12.3 Ink composition 2-23 4.2 28.4 3.5 13.1 Ink composition 2-24 4.9 29.5 5.0 10.9 Ink composition 2-25 4.5 28.9 4.1 12.5 Ink composition 2-26 4.3 29.8 5.1 12.4 Ink composition 2-27 4.4 29.4 4.4 12.5 Ink composition 2-28 4.2 29.2 5.2 11.9 Ink composition 2-29 4.7 29.6 4.2 12.4 Ink composition 2-30 4.6 29.4 4.4 12.9 Ink composition 2-31 4.8 29.3 5.2 11.4 Ink composition 2-32 5.4 29.4 4.3 12.2 Ink composition 2-33 5.0 29.4 5.2 11.4 Ink composition 2-34 5.8 29.5 4.3 12.9 Ink composition 2-35 4.9 29.5 5.2 11.9 Ink composition 2-36 4.8 30.4 4.2 12.9 Ink composition 2-37 4.3 29.8 4.3 12.9 Ink composition 2-38 4.9 30.1 5.2 11.5 Ink composition 2-39 4.2 29.2 5.1 12.8 Ink composition 2-40 4.2 29.2 4.4 11.2 Ink composition 2-41 4.6 29.4 5.2 11.9 Ink composition 2-42 4.6 29.4 4.4 12.9 Ink composition 2-43 5.4 29.4 4.4 12.9 Ink composition 2-44 5.4 29.4 5.2 12.4 Ink composition 2-45 5.8 29.5 4.3 12.2 Ink composition 2-46 5.8 29.5 5.2 12.4 Ink composition 2-47 4.8 30.4 3.9 12.9 Ink composition 2-48 4.8 30.4 5.2 11.9

Luminescent material Viscosity
(cps) Surface tension
(dyne / cm ² ) Voltage
(V) Current Efficiency
(Cd / A) Ink composition 3-1 4.1 29.1 4.1 11.9 Ink composition 3-2 4.8 29.4 5.4 12.8 Ink composition 3-3 4.2 28.4 4.2 13.2 Ink composition 3-4 4.2 29.2 5.1 12.9 Ink composition 3-5 4.5 28.9 4.4 12.9 Ink composition 3-6 4.6 29.4 5.2 11.4 Ink composition 3-7 4.4 29.4 4.4 12.9 Ink composition 3-8 4.8 29.3 5.2 11.9 Ink composition 3-9 4.7 29.6 4.1 12.9 Ink composition 3-10 5.0 29.4 5.7 12.8 Ink composition 3-11 4.8 29.3 4.4 11.9 Ink composition 3-12 4.9 29.5 5.1 11.1 Ink composition 3-13 5.0 29.4 4.3 12.8 Ink composition 3-14 4.3 29.8 5.3 12.8 Ink composition 3-15 4.9 29.5 5.3 12.4 Ink composition 3-16 4.2 29.2 5.4 12.8 Ink composition 3-17 4.3 29.8 4.1 12.9 Ink composition 3-18 4.6 29.4 5.7 12.8 Ink composition 3-19 4.2 29.2 6.8 12.2 Ink composition 3-20 5.4 29.4 5.2 13.9 Ink composition 3-21 4.6 29.4 4.4 12.9 Ink composition 3-22 5.8 29.5 5.2 11.4 Ink composition 3-23 4.1 29.1 4.4 12.9 Ink composition 3-24 4.8 30.4 5.2 12.9 Ink composition 3-25 4.2 28.4 4.9 13.1 Ink composition 3-26 4.9 30.1 5.1 12.9 Ink composition 3-27 4.5 28.9 5.3 12.4 Ink composition 3-28 4.8 29.4 5.7 11.8 Ink composition 3-29 4.4 29.4 4.4 11.9

Luminescent material Viscosity
(cps) Surface tension
(dyne / cm ² ) Voltage
(V) Current Efficiency
(Cd / A) Ink composition 4-1 5.4 29.4 5.0 12.9 Ink composition 4-2 3.9 28.9 6.3 12.4 Ink Composition 4-3 5.8 29.5 5.2 12.4 Ink Composition 4-4 4.0 29.6 5.1 11.8 Ink Composition 4-5 4.8 30.4 5.2 10.9 Ink composition 4-7 4.9 30.1 4.4 12.9 Ink composition 4-8 3.8 29.2 5.2 12.6 Ink composition 4-9 4.2 29.4 4.9 13.1 Ink composition 4-10 4.8 29.6 4.1 12.9 Ink composition 4-11 4.1 29.1 4.3 12.4 Ink composition 4-12 4.5 29.4 4.7 12.8 Ink composition 4-13 4.2 28.4 4.8 11.4 Ink composition 4-14 4.1 29.4 5.2 11.9 Ink composition 4-15 4.5 28.9 5.4 12.9 Ink composition 4-16 4.8 29.6 5.6 10.9 Ink composition 4-17 4.4 29.4 5.1 12.5 Ink composition 4-18 4.2 29.4 6.4 13.4 Ink composition 4-19 4.7 29.6 4.2 12.6 Ink composition 4-20 4.1 29.1 5.1 10.2 Ink composition 4-21 4.8 29.3 4.1 11.9 Ink composition 4-22 5.1 29.4 4.3 12.9 Ink composition 4-23 5.0 29.4 5.2 11.9 Ink composition 4-24 5.2 29.8 4.9 13.1 Ink composition 4-25 4.9 29.5 5.0 12.9 Ink composition 4-26 5.1 28.9 5.3 12.3 Ink Composition 4-27 5.4 29.4 5.7 12.8 Ink Composition 4-28 4.8 29.4 4.0 12.1 Ink Composition 4-29 5.8 29.5 5.2 11.4 Ink composition 4-30 5.4 30.2 4.4 12.9

Luminescent material Viscosity
(cps) Surface tension
(dyne / cm ² ) Voltage
(V) Current Efficiency
(Cd / A) Ink composition 5-1 4.8 29.6 5.1 12.9 Ink composition 5-2 4.9 30.1 4.0 12.5 Ink composition 5-3 4.5 29.4 5.7 12.7 Ink composition 5-4 4.2 29.4 5.1 11.2 Ink composition 5-5 4.1 29.4 4.2 11.9 Ink composition 5-6 4.1 29.1 4.4 12.9 Ink composition 5-7 4.8 29.6 5.1 11.9 Ink composition 5-8 4.2 28.4 4.5 13.2 Ink composition 5-9 5.2 29.1 5.1 12.9 Ink composition 5-10 4.5 28.9 5.0 12.4 Ink composition 5-11 5.3 29.2 5.7 12.8 Ink composition 5-12 4.4 29.4 6.8 10.2 Ink composition 5-13 5.1 29.4 5.2 11.9 Ink composition 5-14 4.7 29.6 4.4 12.8 Ink composition 5-15 5.2 29.8 5.2 12.1 Ink composition 5-16 4.8 29.3 4.2 12.4 Ink composition 5-17 5.1 28.9 5.7 12.8 Ink composition 5-18 5.0 29.4 5.1 11.6 Ink composition 5-19 4.8 29.4 5.2 11.9 Ink composition 5-20 4.9 29.5 4.4 12.9 Ink composition 5-21 5.4 30.2 4.8 12.9 Ink composition 5-22 5.4 29.4 5.1 11.1 Ink composition 5-23 5.8 30.4 5.1 11.9 Ink composition 5-24 5.8 29.5 4.4 12.9 Ink composition 5-25 5.8 29.4 5.0 11.9 Ink composition 5-26 4.9 30.1 4.9 12.9 Ink composition 5-27 4.8 29.6 4.1 12.8 Ink composition 5-28 4.2 29.4 5.2 12.3 Ink composition 5-29 4.5 29.4 4.4 12.8 Ink composition 5-30 4.1 29.1 4.0 12.1 Ink composition 5-31 4.1 29.4 5.1 11.2 Ink composition 5-32 4.2 28.4 4.1 11.8 Ink composition 5-33 4.8 29.6 4.4 12.9 Ink composition 5-34 4.5 28.9 5.2 11.9 Ink composition 5-35 5.2 29.1 4.9 13.1 Ink composition 5-36 4.4 29.4 5.1 13.9 Ink composition 5-37 5.3 29.2 3.9 13.5 Ink composition 5-38 4.7 29.6 4.7 13.7 Ink composition 5-39 5.1 29.4 4.1 12.2 Ink composition 5-40 4.8 29.3 5.2 12.9 Ink composition 5-41 5.2 29.8 4.4 12.9 Ink composition 5-42 5.0 29.4 5.1 12.9 Ink composition 5-43 5.1 28.9 4.5 10.2 Ink composition 5-44 4.9 29.5 5.1 12.9 Ink composition 5-45 4.8 29.4 5.0 13.4 Ink composition 5-46 5.4 29.4 5.1 13.6 Ink composition 5-47 5.4 30.2 6.0 13.4 Comparative Example 1 (Deposition) - - 4.7 11.7

As a result, it was found that the organic electroluminescent device using the ink composition according to the present invention increased the current efficiency by 10% or more as well as the driving voltage as compared with the organic electroluminescent device of Comparative Example 1 using the conventional light emitting material . This is a result of the fact that the combination of the components of the ink composition according to the present invention is more smoothly transferred from the host to the dopant than the host / dopant system of Alq ₃ and C-545T. As a result, it can be seen that the full color organic EL panel has a great effect on maximizing the performance.

While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, and that various changes and modifications may be made without departing from the scope of the invention. It is natural to belong.

Claims (6)

(a) a compound represented by the following general formula (1)
(b) an aliphatic cyclic compound having 5 to 20 carbon atoms substituted with an atom-containing functional group selected from oxygen, sulfur and nitrogen; Aromatic ring compounds having 5 to 20 carbon atoms substituted with an atom-containing functional group selected from oxygen, sulfur and nitrogen; A heterocyclic compound having 5 to 20 nucleus atoms substituted with an atom-containing functional group selected from oxygen, sulfur and nitrogen, or containing a hetero atom selected from oxygen, sulfur and nitrogen,
(c) an organic solvent which is different from the first organic solvent and is selected from the group consisting of an alcohol solvent, a ketone solvent, a cellosolve solvent, a carboxylic acid solvent, a carbitol solvent, an acetate solvent, a lactate solvent, A second organic solvent selected from the group consisting of an aromatic hydrocarbon solvent, an aliphatic hydrocarbon solvent, and an amide solvent
Wherein the ink composition for organic electronic devices comprises:
[Chemical Formula 1]

(In the formula 1,
X is ^{CR 6 R 7, NR 6,} O, S, S (= O), S (= O) 2 and is selected from the group consisting of SiR ⁶ R ^7;
R ¹ to R ⁷ are the same or different from each other and each independently represents hydrogen, deuterium, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ An aryl group, a heteroaryl group having 5 to 40 nuclear atoms, a C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamino group, a C ₆ to C ₄₀ dia Reel amino group, C ₆ ~ C ₄₀ aryl group, C ₃ ~ C ₄₀ cycloalkyl group and nuclear atoms, or selected from the group consisting of a heterocycloalkyl group of 3 to 40, or adjacent groups bonded to the condensed aliphatic ring, a condensed aromatic A ring, a fused heteroaliphatic ring or a fused heteroaromatic ring;
In the above R ¹ to R ⁷ , a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, a C ₂ to C ₄₀ alkynyl group, a C ₆ to C ₄₀ aryl group, A C ₆ to C ₄₀ aryloxy group, a C ₁ to C ₄₀ alkyloxy group, a C ₆ to C ₄₀ arylamino group, a C ₆ to C ₄₀ diarylamino group, a C ₆ to C ₄₀ The arylalkyl group, the C ₃ to C ₄₀ cycloalkyl group and the heterocycloalkyl group having 3 to 40 nuclear atoms are each independently selected from the group consisting of deuterium, a halogen, a nitrile group, a nitro group, a C ₁ to C ₄₀ alkyl group, a C ₂ to C ₄₀ alkenyl group, C ₁ ~ C ₄₀ alkoxy group, C ₁ ~ C ₄₀ of an amino group, an aryl group and the nucleus of a C ₃ ~ C ₄₀ heterocycloalkyl group, C ₆ ~ C ₄₀ cycloalkyl in the group, a number of nuclear atoms of 3 to 40 A heteroaryl group having 5 to 40 atoms and substituted or unsubstituted heteroaryl groups;
And at least two of R ¹ to R ⁴ are each independently a C ₆ to C ₄₀ aryl group. The method according to claim 1,
And an aromatic ketone-based solvent. The method according to claim 1,
Wherein the organic electronic device further comprises a dopant material for an organic electronic device. The method according to claim 1,
Based on the total weight of the ink composition
0.01 to 10% by weight of a compound represented by the general formula (1)
50 to 99.9% by weight of the first organic solvent, and
And 0.1 to 50% by weight of a second organic solvent. 1. An organic electronic device comprising a first electrode, a second electrode, and at least one organic compound layer interposed between the first electrode and the second electrode,
Wherein at least one of the one or more organic layers includes an organic thin film formed using the ink composition according to any one of claims 1 to 4. 6. The method of claim 5,
Wherein the organic thin film formed using the ink composition is contained in the light emitting layer.