KR101597552B1 - The Host Compounds for Phosphorescent Emitter and Organic Light-Emitting Diodes Using This - Google Patents

Abstract

The present invention relates to a compound for a phosphorescent host and an organic light emitting device comprising the same. The compound for a phosphorescent host, according to the present invention, is designed to have a wide band gap by adopting a donor-acceptor-donor (D-A-D) structure and, distinctively, is designed to have high triplet energy (ET) and a high glass transition temperature (Tg), and be atypical materials having high molecular weight by using a thiozanthene structure as a mother nucleus in a center part of an acceptor role and bonding a carbazole or a carboline compound as a donor role around a central atom corresponding to a sulfone structure of the mother nucleus, and thus has long lifespan, electrical mobility and thermal stability.

Description

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a phosphorescent host compound and an organic light-

The present invention relates to a compound for a phosphorescent host and an organic light emitting device including the same. More particularly, the present invention relates to a phosphorescent host compound which adopts a donor-acceptor-donor (DAD) structure to increase the bandgap, and an organic light emitting device having excellent luminescence efficiency while embodying color.

An electroluminescent device (EL device) is a self-luminous display device having a wide viewing angle, excellent contrast, and fast response time.

The EL element is divided into an inorganic EL element and an organic EL element according to a material for forming an emitting layer. Here, the organic EL element has an advantage of being excellent in luminance, driving voltage, and response speed characteristics as compared with an inorganic EL element, and being able to have multiple colors.

A typical organic EL element has a structure in which an anode is formed on a substrate, and a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially formed on the anode. Here, the hole transporting layer, the light emitting layer, and the electron transporting layer are organic thin films made of organic compounds.

The driving principle of the organic EL device having the above-described structure is as follows. When a voltage is applied between the anode and the cathode, holes injected from the anode are transferred to the light emitting layer via the hole transport layer. On the other hand, electrons are injected from the cathode to the light emitting layer via the electron transporting layer, and carriers are recombined in the light emitting layer region to generate an exiton. This exciton is changed from the excited state to the ground state, whereby the molecules of the light emitting layer emit light and an image is formed. The light emitting material is divided into a fluorescent material using a singlet state exciton and a phosphorescent material using a triplet state depending on its light emitting mechanism. Phosphorescent materials generally have an organic-inorganic compound structure containing heavy atoms, and the triplet state excitons, which were originally prohibited by heavy atoms, emit phosphorescence through permissive transition. The phosphorescent material can use a triplet exciton having a probability of generating 75% and can have a much higher luminous efficiency than a fluorescent material using a 25% singlet exciton.

The luminescent layer using a phosphorescent material is composed of a host material and a dopant material that emits light by transferring energy therefrom. Various materials using an iridium metal compound as a dopant material have been reported. Studies on organic light emitting materials using iridium compounds have revealed various phosphorescent materials using iridium and platinum metal compounds at Princeton University and University of Southern California. It is progressing.

Accordingly, the present inventors have been studying a host material and designed to adopt a donor-acceptor-donor (DAD) structure to increase the band gap, while characterizing the thioxanthene structure as a central part of the acceptor And one or two carbazole or carbene compounds as a donor in the vicinity of the central atom corresponding to the sulfonic structure of the mother nucleus and substituted with an amine in the structure and an alkyl or a derivative of a hexagonal ring or a hexagonal ring in the ring When a compound is bonded in a symmetrical or asymmetric structure, it is designed as an amorphous material having a high triple energy (ET) and a high glass transition temperature (Tg) and a high molecular weight, and has a long lifetime, electric mobility and thermal stability And the present invention has been completed.

Korean Patent Laid-Open Publication No. 10-2006-0113935 (entitled "Organic Device for Electroluminescence Device", published on Nov. 03, 2006)

Accordingly, it is an object of the present invention to provide a phosphorescent host compound which adopts a donor-acceptor-donor (D-A-D) structure to increase the band gap.

In addition, another object of the present invention is to provide an organic light emitting device using a phosphorescent host compound which adopts a donor-acceptor-donor (DAD) structure and has a large bandgap.

Accordingly, in order to accomplish the first technical object, the present invention provides a phosphorescent host compound represented by the following general formula (1).

Formula 1

Wherein X and Y are each independently selected from a carbazole group or a carbolyn group selected from an? -Carboline group,? -Carboline group,? -Carboline group, and? -Carboline group, R2 each independently represents a substituted or unsubstituted functional group, which may be substituted by a cyano group, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C14 aryl group, a substituted or unsubstituted N, O, S Wherein at least one of the hydrogen atoms of the unsubstituted moiety is substituted with at least one substituent selected from the group consisting of a halogen atom, a hydroxy group, a nitro group, a cyano group, an amino group, an amidino group, a hydrazine, a hydrazone, A C1-C14 alkyl group, a C2-C14 alkenyl group, a C2-C14 alkynyl group, a C6-C14 aryl group, a C7-C14 arylalkyl group, a C2 A heteroaryl group of -C14, or a heteroalkyl group of C3-C14.

In order to accomplish the second technical object, the present invention provides an organic light emitting device comprising an organic film provided between a pair of electrodes, wherein the organic film includes a phosphorescent host compound represented by Chemical Formula 1 The organic electroluminescent device of the present invention comprises:

Formula 1

Wherein X and Y are each independently selected from a carbazole group or a carbolyn group selected from an? -Carboline group,? -Carboline group,? -Carboline group, and? -Carboline group, R2 each independently represents a substituted or unsubstituted functional group, which may be substituted by a cyano group, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C14 aryl group, a substituted or unsubstituted N, O, S Wherein at least one of the hydrogen atoms of the unsubstituted moiety is substituted with at least one substituent selected from the group consisting of a halogen atom, a hydroxy group, a nitro group, a cyano group, an amino group, an amidino group, a hydrazine, a hydrazone, A C1-C14 alkyl group, a C2-C14 alkenyl group, a C2-C14 alkynyl group, a C6-C14 aryl group, a C7-C14 arylalkyl group, a C2 A heteroaryl group of -C14, or a heteroalkyl group of C3-C14.

The phosphorescent host compound according to the present invention adopts a donor-acceptor-donor (DAD) structure and is designed to have a large bandgap, while characteristically serving as a central portion of the acceptor, with a thioxanthene structure as the parent nucleus, Designed as amorphous material with high triplet energy (ET) and high glass transition temperature (Tg) and high molecular weight by bonding carbazole or carbolin compound as donor role around the central atom corresponding to the solfon structure Thus, the light emitting device using the material can have excellent light emitting characteristics and stability.

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

Hereinafter, the present invention will be described in more detail.

DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS Hereinafter, preferred embodiments of the present invention will be described in detail with reference to the accompanying drawings. Prior to the detailed description of the present invention, terms and words used in the present specification and claims should not be construed as limited to ordinary or dictionary terms. Therefore, the embodiments described in this specification and the configurations shown in the drawings are merely the most preferred embodiments of the present invention and do not represent all the technical ideas of the present invention. Therefore, It is to be understood that equivalents and modifications are possible.

The phosphorescent host compound according to the present invention is designed by adopting a donor-acceptor-donor (DAD) structure in order to increase the band gap between HOMO-LUMO and is characterized in that the central portion of the acceptor serves as a nucleus And a carbazole or a carbene compound is bonded as a donor around the central atom corresponding to the sulfone structure of the nucleus, and one or two carbazole or carbene compounds bonded around the corresponding center atom may form a structure A compound in which an amine and a cyclic ring are substituted with an alkyl or a derivative of a hexagonal ring is included as a symmetrical or asymmetric structure.

Specifically, the phosphorescent host compound according to the present invention has a structure represented by the following Formula 1:

Formula 1

Here, X and Y are each independently selected from a carbazole group or a carboline group, and the above-mentioned carbolin group is preferably an α-carboline group, a β-carboline group, a γ- -Carboline group and a delta-carboline group.

Each of R 1 and R 2 is independently a substituted or unsubstituted functional group, and includes a cyano group, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C14 aryl group, a substituted or unsubstituted N , A C4-C14 heteroaryl group having at least one heteroatom of O, S, wherein the substitution is such that at least one of the hydrogen atoms of the unsubstituted moiety is substituted with a halogen atom, a hydroxy group, a nitro group, C14 alkyl group, C2-C14 alkynyl group, C2-C14 alkynyl group, C6-C14 aryl group, C7-C14 alkyl group, Arylalkyl group of C2-C14, heteroaryl group of C2-C14, or heteroalkyl group of C3-C14.

Representative compounds of formula (1) according to the present invention are compounds of formula (2) wherein X and Y are simultaneously carbazole.

(2)

Typical examples of the compound of Formula 1 according to the present invention include those wherein X and Y are both an? -Carboline group, a? -Carboline group, a? -Carboline group, is a compound of the following formulas (3) to (6) which is a delta-carboline group.

(3)

Formula 4

Formula 5

6

Typical examples of the compound of Formula 1 according to the present invention include those wherein X or Y is an? -Carboline group and Y or X is? -Carboline group,? -Carboline group, Carboline group or? -Carboline group, and X and Y are not the same as in the following formulas (7) to (9).

Formula 7

8

Formula 9

Typical examples of the compound of Formula 1 according to the present invention include compounds wherein X or Y is a carbazole group and Y or X is an? -Carboline group,? -Carboline group,? -Carboline group or? -Carboline group, and X and Y are not the same.

10

Formula 11

Formula 12

Formula 13

Representative compounds of formula (I) according to the present invention are those wherein X or Y is a? -Carboline group and Y or X is a? -Carboline group or? -Carboline group, respectively -carboline, and X and Y are not the same.

Formula 14

Formula 15

Typical examples of the compound of Formula 1 according to the present invention are those wherein X or Y is a? -Carboline group, Y or X is? -Carboline, X and Y are not the same Lt; / RTI >

A phosphorescent host compound represented by the following formula (16).

Formula 16

Preferred compounds of formula (I) according to the present invention are the following compounds.

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

,

In the above formulas, "unsubstituted alkyl group" or "unsubstituted alkoxy" means an alkyl group having 1 to 14 carbon atoms (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, And the term "substituted alkyl group" or "substituted alkoxy" refers to a hydrogen of the above unsubstituted alkyl moiety, Wherein at least one of the atoms is a halogen atom, a hydroxy group, a nitro group, a cyano group, an amino group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, C14 alkenyl group, C2-C14 alkynyl group, C6-C14 aryl group, C7-C14 arylalkyl group, C2-C14 heteroaryl group, or C3-C14 heteroalkyl group.

The term "unsubstituted alkenyl group" means alkenyl having 2 to 14 carbon atoms (eg, ethene, prostene, butene, pentene, hexene, etc., and isomers thereof) having at least one double bond, Substituted alkenyl group "means that at least one hydrogen atom of the above-mentioned unsubstituted alkenyl group is substituted with the same substituent as the above-mentioned alkyl group.

"Unsubstituted aryl group ", alone or in combination, refers to an aromatic carbon ring having from 6 to 14 carbon atoms including at least one ring, which rings may be attached together or fused together by a pendant method. "Substituted aryl group" means that at least one hydrogen atom in the unsubstituted aryl group is substituted with the same substituent as in the case of the above-mentioned alkyl group.

The term "unsubstituted arylalkyl group" means that in the aryl group as defined above, some of the hydrogen atoms are replaced by a group such as lower alkyl, such as methyl, ethyl, propyl, and the like. The term "substituted arylalkyl group" means that at least one hydrogen atom in the unsubstituted arylalkyl group is substituted with the same substituent as in the case of the alkyl group described above.

"Unsubstituted aryloxy group" means an aryl group as defined above in which oxygen is substituted, such as phenyloxy, naphthylenoxy, diphenyloxy, and the like. The "substituted aryloxy group" means that at least one hydrogen atom in the unsubstituted aryloxy group is substituted with the same substituent as the alkyl group described above.

The term "unsubstituted heteroaryl group" refers to a monovalent monocyclic or bicyclic monovalent group of 2 to 14 ring atoms having the remaining ring atoms C, containing 1, 2 or 3 heteroatoms selected from N, O, Refers to a cyclic aromatic divalent organic compound, and specific examples thereof include thienyl, pyridyl, furyl, and the like. The "substituted heteroaryl group" means that at least one hydrogen atom in the unsubstituted heteroaryl group is substituted with the same substituent as in the case of the alkyl group described above.

The term " unsubstituted heteroarylalkyl group "means that some of the hydrogen atoms of the aforementioned heteroaryl groups are substituted with lower alkyl groups, and" substituted heteroarylalkyl group "means that at least one hydrogen atom of the unsubstituted heteroarylalkyl group Means that the same substituent as in the case of one alkyl group is substituted.

"Unsubstituted heteroaryloxy group" means that oxygen is bonded to a heteroaryl group as defined above. The "substituted heteroaryloxy group" means that at least one hydrogen atom in the unsubstituted heteroaryloxy group is substituted with the same substituent as the alkyl group described above.

The phosphorescent host compound represented by Formula 1 according to the present invention employs a donor-acceptor-donor structure having a difference in band gap within a molecule, has a band gap of 3.0 eV or more, Thereby exhibiting high luminous efficiency. The phosphorescent host compound represented by Formula 1 may be used for realizing color in an organic light emitting device, and may be used for realizing blue color.

Hereinafter, a structure and a manufacturing method of an organic light emitting device employing a phosphorescent host compound according to the present invention will be described.

The organic light emitting device according to the present invention may employ a conventional light emitting device structure, and the structure may be changed if necessary. Basically, the organic light emitting device has a structure including an organic film (light emitting layer) between a first electrode (anode electrode) and a second electrode (cathode electrode), and if necessary, a hole injection layer, a hole transport layer, An electron injection layer or an electron transport layer may be further included. Reference is made to Fig. 1 for explaining the structure of the light emitting device of the present invention.

Referring to FIG. 1, the organic light emitting device according to the present invention includes a light emitting layer 50 between an anode electrode 20 and a cathode electrode 80, and includes a light emitting layer 50 between the anode electrode 20 and the light emitting layer 50 And includes an electron transport layer 50 and an electron injection layer 70 between the light emitting layer 50 and the cathode electrode 80. The electron transport layer 50 and the electron injection layer 70 are formed on the light emitting layer 50 and the cathode electrode 80,

Meanwhile, the organic light emitting device of FIG. 1 according to one embodiment of the present invention is manufactured through the following process, which is only one example and is not limited thereto.

First, an anode electrode material is coated on the substrate 10 to form an anode electrode 20. Here, as the substrate 10, a substrate generally used in this field can be used, and a glass substrate or a transparent plastic substrate having excellent transparency, surface smoothness, ease of handling, and waterproofness is particularly preferable. As the material for the anode electrode formed on the substrate, indium tin oxide (ITO), tin oxide (SnO 2), zinc oxide (ZnO), etc., which are transparent and excellent in conductivity, may be used.

A hole injecting layer (HIL) 30 is selectively formed on the anode electrode 20. At this time, the hole injection layer is formed by a conventional method such as vacuum deposition or spin coating. The material for the hole injection layer is not particularly limited, but CuPc (copper phthalocyanine) or IDE 406 (Idemitsu Kosan) may be used.

Next, the hole transport layer (HTL) 40 is formed on the hole injection layer 30 by a conventional method such as vacuum deposition or spin coating. The material for the hole transporting layer is not particularly limited, but a material such as N, N'-diphenyl-N, N'-bis (1-naphthyl) -1,1'-biphenyl-4,4'- diamine (NPB) Diamine (TPD), N, N'-di (naphthalene-1-yl) N, N'-diphenyl-benzidine:? -NPD), and the like can be used.

Then, a light emitting layer (EML) 50 is formed on the hole transport layer 40. The light emitting layer forming material may include at least one selected from the phosphorescent host compounds according to the present invention as a light emitting host material, and may have a single layer or a multilayer structure of two or more layers. At this time, the compound of the formula (1) may be contained alone or mixed with other compounds known in the art, for example, a blue light emitting dopant (an iridium compound such as FIrppy or FIrpic). The phosphorescent host compound may be contained in the light emitting layer within the range of 1 to 95 wt% based on the total weight of the materials constituting the light emitting layer.

The phosphorescent host compound may be formed by a vacuum deposition method, or may be deposited by a wet process such as spin coating, or laser induced thermal imaging (LITI) may be used.

Optionally, a hole blocking layer (HBL) may be formed on the light emitting layer 50 to prevent the excitons formed from the light emitting material from moving to the electron transporting layer or to prevent the holes from moving to the electron transporting layer 60, The material for the hole blocking layer is not particularly limited, but a phenanthroline compound (for example, BCP) can be used. This can be formed by a vacuum deposition method or a spin coating method.

Further, an electron transport layer (ETL) 60 may be formed on the light emitting layer 50, and a vacuum deposition method or a spin coating method may be used. The material for the electron transport layer is not particularly limited, but TBPI, an aluminum complex (for example, Alq3 (tris (8-quinolinolato) -aluminum)) can be used.

An electron injection layer (EIL) 70 may be formed on the electron transport layer 60 using a method such as vacuum deposition or spin coating. The material for the electron injection layer 70 is not particularly limited, NaCl, CsF, and the like can be used.

Then, a cathode electrode 80 is formed on the electron injection layer 70 through vacuum deposition to complete the light emitting device. Here, as the metal for the cathode, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium- -Ag) or the like is used.

The organic electroluminescent device according to the present invention has a laminated structure as shown in FIG. 1, and it is also possible to form one or more intermediate layers, for example, a hole blocking layer, if necessary. Further, the thickness of each layer of the light emitting element can be determined as needed within a range generally used in this field.

Hereinafter, the present invention will be described in more detail by way of examples, but the present invention is not limited to the following examples.

Synthesis Example 1

Synthesis of 2,7-dimethyl-9H-thioxan-9-one

15.5 g (0.06 mol) of 5-methyl-2- (m-tolylthio) benzoic acid was added to 150 ml of sulfuric acid under nitrogen atmosphere, and the mixture was stirred at 100 DEG C for 2 hours and then slowly cooled to ice water. And the resulting solid was filtered. The resulting solid was dissolved in 300 ml of chloroform, washed and extracted with 10% sodium carbonate solution several times, treated with anhydrous magnesium sulfate, and the filtrate was distilled under reduced pressure. The residue was purified by silica gel column chromatography using hexane and ether 10: 2.66 g (25.4%) of the target compound 2,7-dimethyl-9H-thioxan-9-one was obtained by chromatography.

Synthesis Example 2

Synthesis of 3,6-dibromo-9H-thioxan-9-one

(0.01 mol) of 4-bromo-2 - ((3-bromophenyl) thio) benzoic acid was added to 150 g of polyphosphoric acid, stirred at 130 ° C for 6 hours and then cooled to room temperature and slowly added to 1 L of ice water Stirred vigorously for 30 minutes. The resulting precipitate was filtered and washed several times with water and 10% sodium bicarbonate solution. To the resulting solid was added 2.48 g of p-toluenesulfonamide, 1.2 g of anhydrous sodium acetate, 0.1 g of cupper (Ⅱ) acetate and 40 mL of 1-pentanol, The mixture was stirred at the reflux time. After stirring, the reaction solvent was distilled off under reduced pressure, ethyl ether was added to the residue, and the resulting solid was filtered. The solid obtained was dissolved in 10 ml of 47% hydrobromic acid and 1 g of phenol, refluxed for 2 hours and stirred at room temperature, The organic layer was treated with anhydrous magnesium sulfate, filtered and distilled under reduced pressure. The resulting residue was recrystallized by adding 30 mL of a 1: 1 mixture of chloroform and ethanol to obtain a target compound 3,6-di (17.8%) of bromo-9H-thioxan-9-one.

Synthesis Example 3

Preparation of 2,7-dimethyl-9H-thioxan-9-one 10,10-dioxide

10 g (0.042 mol) of 2,7-dimethyl-9H-thioxan-9-one was added to 200 ml of glacial acetic acid and stirred for 30 minutes. 10.2 g of 34.5% hydrogen peroxide was added and refluxed for 2 hours. After confirming the termination of the reaction and stirring at room temperature for 2 hours, the resulting precipitate was filtered, washed with n-hexane and dried to obtain 8.6 g of 2,7-dimethyl-9H-thioxan-9-one 10,10- 75.4%).

Synthesis Example 4

Synthesis of 3,6-dibromo-9H-thioxan-9-one 10,10-dioxide

10 g (0.027 mol) of 3,6-dibromo-9H-thioxan-9-one was placed in 150 ml of glacial acetic acid, stirred for 30 minutes, and then 6.56 g of 34.5% hydrogen peroxide was added and refluxed for 2 hours. The reaction was terminated and treated in the same manner as in Synthesis Example 3 to obtain 8.2 g (75.9%) of 3,6-dibromo-9H-thioxan-9-one 10,10-dioxide as a target compound.

Synthesis Example 5

Synthesis of 9,9-bis (9-ethyl-9H-carbazol-3-yl) -2,7-dimethyl-9H-thioxane 10,10-

11.7 g (0.06 mol) of 9-ethyl-9H-pyrido [2,3-b] indole and 5.4 g (0.02 mol) of 10,10- And the reaction solution was heated at 90 캜. A solution prepared by dissolving 14.2 g (0.1 mol) of phosphorus pentoxide in 170 g of methanesulfonic acid was slowly added to the reaction solution over 1 hour and the reaction was carried out for 30 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, 800 ml of methanol was added, and the mixture was stirred for 1 hour. The resultant crystals were filtered and washed with methanol. The resulting solid was refluxed for 1 hour with 400 ml of acetone, stirred at room temperature for 1 hour, filtered, washed with acetone and filtered. The resulting solid was purified by silica gel chromatography using a 1: 3 mixed solution of dichloromethane and n-hexane as the eluent to obtain the objective compound 9,9-bis (9-ethyl-9H-carbazol- -9H-thioxane 10,10-dioxide (5.9 g, 45.7%).

Synthesis Example 6

Synthesis of 9,9-bis (9-ethyl-9H-carbazol-3-yl) -9H-thioxane-2,7-dicarbonitrile 10,10-

(0.022 mol) of 9-oxo-9H-thioxane-2,7-dicarbonitrile 10,10-dioxide and 12.9 g (0.066 mol) of 9- Were all added to the reaction vessel under a nitrogen atmosphere and heated to 110 占 폚. A solution of 15.6 g (0.11 mol) of phosphorus pentoxide in 175 g of methanesulfonic acid was gradually added to the reaction solution over 1 hour, and the reaction was carried out for 48 hours. After confirming the completion of the reaction, the target compound 9,9-bis (9-ethyl-9H-carbazol-3-yl) -9H-thioxane- 6.3 g (42.8%) of 10-dioxide was obtained

Synthesis Example 7

Synthesis of 3,6-diphenyl-9H-thioxan-9-one 10,10-dioxide

(0.02 mol) of 3,6-dibromo-9H-thioxan-9-one 10,10-dioxide and 2.6 g (0.021 mol) of phenylboronic acid were dissolved in 60 mL of toluene, and 6.1 g ) Was dissolved in 30 ml of water, and 30 ml of ethanol was added thereto. After the temperature of the mixed solution was raised to 40 ° C, 116 mg (0.5 mol%) of tetrakis (triphenylphosphine) palladium (0) was added in one portion, refluxed at 80 ° C. and reacted for 5 hours. After confirming the termination of the reaction, ethanol was removed by using a trap, and 40 ml of toluene was added thereto, followed by filtration and washing with saturated brine three times. To the filtrate, 0.5 g of activated carbon and anhydrous magnesium were added and stirred for 30 minutes, followed by filtration and distillation under reduced pressure to obtain 7.2 g (90.8%) of the target compound 3,6-diphenyl-9H-thioxan-9-one 10,10 dioxide.

Synthesis Example 8

Synthesis of 9,9-bis (9-ethyl-9H-carbazol-3-yl) -3,6-diphenyl-9H-thioxane 10,10-

(0.018 mol) of 3,6-diphenyl-9H-thioxan-9-one 10,10-dioxide and 10.3 g (0.053 mol) of 9-ethyl-9H- Were all added to the reaction vessel under the atmosphere, and heated to 110 占 폚. A solution prepared by dissolving 12.8 g (0.09 mol) of phosphorus pentoxide in 140 g of methanesulfonic acid was slowly added to the reaction solution over 1 hour, and the reaction was carried out for 30 hours. The reaction was terminated and 9,9-bis (9-ethyl-9H-carbazol-3-yl) -3,6-diphenyl-9H-thioxane 10,10-dioxide was treated in the same manner as in Synthesis Example 5 To obtain 8.8 g (63.8%) of the desired compound.

Synthesis Example 9

Synthesis of 3,6-di (pyridin-4-yl) -9H-thioxan-9-one 10,10-dioxide

(0.015 mol) of 3,6-dibromo-9H-thioxan-9-one 10,10-dioxide and 1.93 g (0.016 mol) of phenylboronic acid were dissolved in 50 mL of toluene. 4.56 g ) Was dissolved in 25 ml of water, and 25 ml of ethanol was added thereto. After the temperature of the mixed solution was raised to 40 ° C, 173 mg (1 mol%) of tetrakis (triphenylphosphine) palladium (0) was added in one portion, refluxed at 80 ° C. and reacted for 5 hours. After confirming the termination of the reaction, the reaction solution was filtered and distilled under reduced pressure. 200 ml of dichloromethane was added to the residue, which was then washed and extracted three times with purified water. The filtrate was treated by adding anhydrous magnesium, filtered and distilled under reduced pressure to obtain 4.6 g (77.1%) of the target compound 3,6-di (pyridin-4-yl) -9H-thioxan-9-one 10,10- .

Synthesis Example 10

Synthesis of 9,9-bis (9-ethyl-9H-carbazol-3-yl) -3,6-di (pyridin-4-yl) -9H-thioxane 10,10-

A mixture of 4 g (0.01 mol) of 3,6-di (pyridin-4-yl) -9H-thioxan-9-one 10,10- (0.03 mol) were all added to the reaction vessel under a nitrogen atmosphere and heated to 100 占 폚. A solution prepared by dissolving 7.1 g (0.05 mol) of phosphorus pentoxide in 80 g of methanesulfonic acid was slowly added to the reaction solution over 1 hour and the reaction was carried out for 30 hours. (9-ethyl-9H-carbazol-3-yl) -3,6-di (pyridin-4-yl) -9H-thioxane 10,10- 5, 4.3 g (55.8%) of the desired compound was obtained.

Synthesis Example 11

9,9-bis (9-ethyl-9H-pyrido [2,3-b] indol-6-yl) -3,6-di (pyridin- Synthesis of

10 g (0.025 mol) of 10,6-di (pyridin-4-yl) -9H-thioxan-9- (0.075 mol) were all added to the reaction vessel under a nitrogen atmosphere and heated at 90 캜. A solution of 18.5 g (0.13 mol) of phosphorus pentoxide in 210 g of methanesulfonic acid was slowly added to the reaction solution over 1 hour, and the reaction was carried out for 48 hours. After completion of the reaction, 600 ml of methanol was added thereto at room temperature, and the mixture was stirred for 1 hour. The resulting crystals were filtered and washed with methanol. 350 ml of acetone was added to the solid obtained, and the mixture was refluxed for 1 hour and further stirred at room temperature for 1 hour, filtered, washed with acetone, and filtered. The resulting solid was purified by silica gel chromatography using a 1: 3 mixed solution of dichloromethane and ethyl acetate as the eluent to obtain the target compound 9,9-bis (9-ethyl-9H-pyrido [2,3- b] indol- ) -3,6-di (pyridin-4-yl) -9H-thioxane 10,10-dioxide in a yield of 53.4%.

Synthesis Example 12

9,9- Synthesis of bis (9-ethyl-9H-pyrido [3,4-b] indol-6-yl) -3,6-di (pyridin-4-yl) -9H-10,10-

10 g (0.025 mol) of 10,6-di (pyridin-4-yl) -9H-thioxan-9- (0.075 mol) were all added to the reaction vessel under a nitrogen atmosphere, and heated at 100 占 폚. A solution of 18.5 g (0.13 mol) of phosphorus pentoxide in 210 g of methanesulfonic acid was slowly added to the reaction solution over 1 hour, and the reaction was carried out for 48 hours. (9-ethyl-9H-pyrido [3,4-b] indol-6-yl) -3,6-di Pyridin-4-yl) -9H-10,10-dioxide (9.7 g, 50.3%).

Synthesis Example 13

(5-ethyl-5H-pyrido [4,3-b] indol-8-yl) -3,6-di (pyridin- 4- yl) -9H-thioxane 10,10- Synthesis of

10 g (0.025 mol) of 10,6-di (pyridin-4-yl) -9H-thioxan-9- (0.075 mol) were all added to the reaction vessel under a nitrogen atmosphere, and heated at 100 占 폚. A solution of 18.5 g (0.13 mol) of phosphorus pentoxide in 210 g of methanesulfonic acid was slowly added to the reaction solution over 1 hour, and the reaction was carried out for 48 hours. (5-ethyl-5H-pyrido [4,3-b] indol-8-yl) -3,6-di Pyridin-4-yl) -9H-thioxane 10,10-dioxide (10.2 g, 52.8%).

Synthesis Example 14

(5-ethyl-5H-pyrido [3,2-b] indol-8-yl) -3,6-di (pyridin-4-yl) -9H-thioxane 10,10- Synthesis of

10 g (0.025 mol) of 10,6-di (pyridin-4-yl) -9H-thioxan-9-one 10,10- (0.075 mol) were all added to the reaction vessel under a nitrogen atmosphere and heated at 90 캜. A solution of 18.5 g (0.13 mol) of phosphorus pentoxide in 210 g of methanesulfonic acid was slowly added to the reaction solution over 1 hour, and the reaction was carried out for 48 hours. (5-ethyl-5H-pyrido- [3,2-b] indol-8-yl) -3,6-di (Pyridin-4-yl) -9H-thioxane 10,10-dioxide (63.7%).

Synthesis Example 15

(9-ethyl-9H-pyrido [3,4-b] indol-6-yl) - Synthesis of 3,6-di (pyridin-4-yl) -9H-thioxane 10,10-dioxide

10 g (0.025 mol) of 10,6-di (pyridin-4-yl) -9H-thioxan-9- (0.038 mol) of 9-ethyl-9H-pyrido [3,4-b] indole were added to the reaction vessel under nitrogen atmosphere and heated at 110 占 폚. A solution of 18.5 g (0.13 mol) of phosphorus pentoxide in 210 g of methanesulfonic acid was slowly added to the reaction solution over 1 hour, and the reaction was carried out for 48 hours. (9-ethyl-9H-pyrido [2,3-b] indol-6-yl) -9- (33.2%) of pyrido [3,4-b] indol-6-yl) -3,6-di (pyridin-4-yl) -9H-thioxane 10,10-dioxide.

Synthesis Example 16

Pyrido [2,3-b] indol-8-yl) -9- (9-ethyl-9H- Synthesis of 3,6-di (pyridin-4-yl) -9H-thioxane 10,10-dioxide

10 g (0.025 mol) of 10,6-di (pyridin-4-yl) -9H-thioxan-9- (0.038 mol) of 5-ethyl-5H-pyrido [4,3-b] indole were added to the reaction vessel under nitrogen atmosphere and heated at 110 ° C. A solution of 18.5 g (0.13 mol) of phosphorus pentoxide in 210 g of methanesulfonic acid was slowly added to the reaction solution over 1 hour, and the reaction was carried out for 48 hours. The reaction was terminated and the product was treated in the same manner as in Synthesis Example 11 to obtain the target compound 9- (5-ethyl-5H-pyrido [4,3- b] indol-8- (30.0%) of [2,3-b] indol-6-yl) -3,6-di (pyridin-4-yl) -9H-thioxane 10,10-

Synthesis Example 17

Pyrido [2,3, b] indol-8-yl) -9- (9-ethyl-9H- Synthesis of 3,6-di (pyridin-4-yl) -9H-thioxane 10,10-dioxide

10 g (0.025 mol) of 10,6-di (pyridin-4-yl) -9H-thioxan-9- (0.038 mol) of 5-ethyl-5H-pyrido [3,2-b] indole were added to the reaction vessel under nitrogen atmosphere and heated at 110 ° C. A solution of 18.5 g (0.13 mol) of phosphorus pentoxide in 210 g of methanesulfonic acid was slowly added to the reaction solution over 1 hour, and the reaction was carried out for 48 hours. Ethyl-5H-pyrido [3,2-b] indol-8-yl) -9- (9- (24.9%) of pyrido [2,3-b] indol-6-yl) -3,6-di (pyridin-4-yl) -9H-thioxane 10,10-dioxide.

Synthesis Example 18

(9-ethyl-9H-carbazol-3-yl) -9- (9-ethyl-9H-pyrido [2,3- b] indol- 4-yl) -9H-thioxane 10,10-dioxide

10 g (0.025 mol) of 10,6-di (pyridin-4-yl) -9H-thioxan-9- (0.038 mol) of 9-ethyl-9H-carbazole and 7.42 g (0.038 mol) of 9-ethyl-9H-carbazole were added to the reaction vessel under a nitrogen atmosphere and heated at 110 占 폚. A solution of 18.5 g (0.13 mol) of phosphorus pentoxide in 210 g of methanesulfonic acid was slowly added to the reaction solution over 1 hour, and the reaction was carried out for 48 hours. (9-ethyl-9H-carbazol-3-yl) -9- (9-ethyl-9H-pyrido [2,3- b ] Indol-6-yl) -3,6-di (pyridin-4-yl) -9H-thioxane 10,10-dioxide in an amount of 7.8 g (40.4%).

Synthesis Example 19

Synthesis of 9,9-bis (9- (2-ethylhexyl) -9H-carbazol-3-yl) -3,6-di (pyridin-4-yl) -9H-thioxane 10,10-

(0.02 mol) of 9,6-di (pyridin-4-yl) -9H-thioxan-9-one 10,10-dioxide and 16.7 g of 9- (2-ethylhexyl) mol) were all added to the reaction vessel under a nitrogen atmosphere and heated at 95 占 폚. A solution prepared by dissolving 14.2 g (0.10 mol) of phosphorus pentoxide in 195 g of methanesulfonic acid was slowly added to the reaction solution over 1 hour, followed by reaction for 48 hours. After completion of the reaction, the reaction mixture was treated in the same manner as in Synthesis Example 11, and a mixed solution of ethyl acetate and n-hexane 2: 3 was used as an eluent to obtain the desired compound 9,9-bis (9- (2-ethylhexyl) -9H-carbazol-3-yl) -3,6-di (pyridin-4-yl) -9H-thioxane 10,10-dioxide 13.4g (71.7%).

Synthesis Example 20

Synthesis of 9,9-bis (9-phenyl-9H-carbazol-3-yl) -3,6-di (pyridin-4-yl) -9H-thioxane 10,10-

(0.02 mol) of 10,6-di (pyridin-4-yl) -9H-thioxan-9- Were all added to the reaction vessel and heated at 90 占 폚. A solution prepared by dissolving 14.2 g (0.10 mol) of phosphorus pentoxide in 200 g of methanesulfonic acid was gradually added to the reaction solution over 1 hour and the reaction was carried out for 48 hours. (9-phenyl-9H-carbazol-3-yl) -3,6-di (pyridin-4-yl) -9H-thio (74.0%) of 10,10-zandane 10,10-dioxide.

Synthesis Example 21

Synthesis of 3,6-di (1,3,5-triazin-2-yl-9H-thioxan-9-one 10,10-dioxide

(0.015 mol) of 3,6-dibromo-9H-thioxan-9-one 10,10-dioxide and 2 g (0.016 mol) of (1,3,5-triazin- A solution of 4.56 g (0.033 mol) of potassium carbonate dissolved in 25 ml of water was added to the solution, and 25 ml of ethanol was added thereto. After the temperature of the mixed solution was raised to 40 ° C, 173 mg (1 mol%) of tetrakis (triphenylphosphine) palladium (0) was added in one portion, and the mixture was refluxed at 80 ° C. and reacted for 12 hours. After confirming the termination of the reaction, the reaction solution was filtered, and the residue obtained by distillation under reduced pressure was dissolved in methylene chloride (200 mL) and extracted three times with purified water. The filtrate was treated with magnesium anhydride, filtered and distilled under reduced pressure to obtain 4.0 g of 3,6-di (1,3,5-triazin-2-yl-9H-thioxan-9-one 10,10- (66.8%).

Synthesis Example 22

Synthesis of 9,9-bis (9-ethyl-9H-carbazol-3-yl) -3,6-di (1,3,5-triazin-2-yl) -9H-thioxane 10,10- synthesis

4 g (0.01 mol) of 10,10-dioxide and 9-ethyl-9H-pyrido [2,3 (0.053 mol) of phosphorus pentoxide in 80 g of methanesulfonic acid was added to the reaction solution under the nitrogen atmosphere to prepare a solution of 1 (9-ethyl-9H-carbazol-3-yl) -3,6-di (1,3,5-triazine- 2-yl) -9H-thioxane 10,10-dioxide was treated in the same manner as in Synthesis Example 5 to obtain the title compound (5.88 g, 76%).

Synthesis Example 23

Synthesis of 3,6-di (pyrimidin-5-yl) -9H-thioxan-9-one 10,10-dioxide

(0.015 mol) of 3,6-dibromo-9H-thioxan-9-one 10,10-dioxide and 1.98 g (0.016 mol) of pyrimidin-5-ylboronic acid were dissolved in 50 ml of toluene, (0.033 mol) in 25 mL of water was added to the solution, and then 25 mL of ethanol was added. After the temperature of the mixed solution was raised to 40 ° C, 173 mg (1 mol%) of tetrakis (triphenylphosphine) palladium (0) was added in one portion, and the mixture was refluxed at 80 ° C. and reacted for 12 hours. After completion of the reaction, the reaction mixture was treated in the same manner as in Synthesis Example 21 to obtain 4.8 g (80.0%) of 3,6-di (pyrimidin-5-yl) -9H-thioxan- ≪ / RTI >

Synthesis Example 24

Synthesis of 9,9-bis (9-ethyl-9H-carbazol-3-yl) -3,6-di (pyrimidin-5-yl) -9H-thioxane 10,10-

(0.01 mol) of 10,6-di (pyrimidin-5-yl) -9H-thioxan-9- Were all added to the reaction vessel and heated to 100 占 폚. A solution prepared by dissolving 7.1 g (0.05 mol) of phosphorus pentoxide in 80 g of methanesulfonic acid was gradually added to the reaction solution over 1 hour, followed by reaction for 48 hours. (9-ethyl-9H-carbazol-3-yl) -3,6-di (pyrimidin-5-yl) - 5.5 g (71.2%) of 9H-thioxane 10,10-dioxide was obtained.

Synthesis Example 25

Synthesis of 3,6-di (furan-2-yl) -9H-thioxan-9-one 10,10-dioxide

(0.015 mol) of 3,6-dibromo-9H-thioxan-9-one 10,10-dioxide and 1.8 g (0.016 mol) of furan-2-ylboronic acid were dissolved in 50 ml of toluene. Potassium carbonate 4.56 g (0.033 mol) in 25 mL of water was added thereto, followed by addition of 25 mL of ethanol. After the temperature of the mixed solution was raised to 40 ° C, 173 mg (1 mol%) of tetrakis (triphenylphosphine) palladium (0) was added in one portion, and the mixture was refluxed at 80 ° C. and reacted for 12 hours. After completion of the reaction, the reaction mixture was treated in the same manner as in Synthetic Example 21 to obtain 3.9 g (69.1%) of the target compound 3,6-di (furan-2-yl) -9H-thioxan-9-one 10,10- .

Synthesis Example 26

Synthesis of 9,9-bis (9-ethyl-9H-carbazol-3-yl) -3,6-di (furan-2-yl) -9H-thioxane 10,10-

3.76 g (0.01 mol) of 10,6-di (furan-2-yl) -9H-thioxan-9- Were all added to the reaction vessel and heated to 100 占 폚. A solution prepared by dissolving 7.1 g (0.05 mol) of phosphorus pentoxide in 80 g of methanesulfonic acid was gradually added to the reaction solution over 1 hour, followed by reaction for 48 hours. (9-ethyl-9H-carbazol-3-yl) -3,6-di (furan-2-yl) -9H -Thioxane 10,10-dioxide (61.4%).

Test Example 1

(9-ethyl-9H-carbazol-3-yl) -3,6-di (pyridin-4-yl) -9H-thioxane 10,10- Pyrido [2,3-b] indol-6-yl) -9- (9-ethyl- (9-ethyl-9H-carbazol-3-yl) -9- (pyridin-4-yl) -9H-thioxane 10,10- (9-ethyl-9H-pyrido [2,3-b] indol-6-yl) -3,6-di (pyridin- (9-phenyl-9H-carbazol-3-yl) -3,6-di (pyridin-4-yl) -9H-thioxane 10,10- (9-ethyl-9H-carbazol-3-yl) -3,6-di (1,3,5-triazin-2-yl) -9H-thioxane 10,10- Representative physical properties of Synthesis Example 22) were evaluated, and the results are shown in Table 1 below.

Properties
UV max
(nm) PL max
(nm) HOMO
(eV) LUMO
(eV) Band gap
(eV) Ti
(eV) TID
(° C) Tm
(° C) Tg
(° C) Synthesis Example 10 304, 357, 350 370 5.5 2.2 3.3 2.9 330 301 199 Synthesis Example 16 310, 340, 355 367 5.6 2.11 3.49 2.96 380 340 209 Synthesis Example 18 315, 327, 349 357 5.55 2.09 3.46 2.97 377 337 211 Synthesis Example 20 305, 327, 347 355 5.53 2.06 3.47 2.99 365 341 201 Synthesis Example 22 309, 317, 351 354 5.54 2.06 3.48 2.98 370 340 203

UVmax: absorption wavelength of the substance measured from the spectrometer and cyclic voltammetry

PLmax: emission wavelength of a substance measured from spectrometer and cyclic voltammetry

HOMO, LUMO, Bandgap: The electrical properties of the material measured from the spectrometer and cyclic voltammetry (blue bandgap should have a wide band gab of> 3.0 eV).

T1: Triplet energy of the material measured from spectrometer and cyclic voltammetry (confirmed by phosphorescence measurement at 77K)

TID: Degradation temperature of the substance (confirmed by TGA)

Tm: melting point

Tg: glass transition temperature

Effective energy transfer can occur because the triplet energy (T1) of the host material synthesized according to the present invention is higher than the triplet energy (2.7 eV) of a typical dopant material (e.g., Firpic) Lt; RTI ID = 0.0 > Tg. ≪ / RTI >

Example 1

The ITO substrate was patterned to have a light emitting area of 3 mm x 3 mm and then cleaned. After the substrate was mounted in a vacuum chamber, the base pressure was adjusted to 1 × 10 -6 torr. Then, NPB was formed as a hole transport layer on the anode ITO to a thickness of 40 nm, and 9,9 (9-ethyl-9H-carbazol-3-yl) -3,6-di (pyridin-4-yl) -9H- thioxane 10,10-dioxide and dopant [FCNIr] 11% in a thickness of 20 nm. Thereafter, TPBI was vacuum-deposited on the light-emitting layer to form an electron transport layer having a thickness of 50 nm, an electron injection layer, LiF, to a thickness of 1.0 nm, and a cathode, Al, to a thickness of 500 nm to form an organic light- . Then, the luminescent characteristics were evaluated, and the results are shown in Table 2 below.

Example 2

Pyrido [2,3-b] indol-8-yl) -9- (9-ethyl-9H-pyrido [ 6-yl) -3,6-di (pyridin-4-yl) -9H-thioxane 10,10-dioxide was used as a host in the light emitting layer. Experimental procedure was the same as Example 1, Table 2 shows the results.

Example 3

(9-ethyl-9H-pyrido [2,3-b] indol-6-yl) -3 , 6-di (pyridin-4-yl) -9H-thioxane 10,10-dioxide was used as a host in the light emitting layer. Experimental procedures were the same as in Example 1, and the results are shown in Table 2 below.

Example 4

(9-phenyl-9H-carbazol-3-yl) -3,6-di (pyridin-4-yl) -9H-thioxane 10,10-dioxide prepared in Synthesis Example 20 The emissive layer was used as a host and the experimental procedure was the same as in Example 1. The results are shown in Table 2 below.

Example 5

Synthesis of 9,9-bis (9-ethyl-9H-carbazol-3-yl) -3,6-di (1,3,5-triazin- Xanthine 10,10-dioxide was used as the host of the luminescent layer. Experimental procedures were the same as in Example 1, and the results are shown in Table 2 below.

Comparative Example 1

An organic light emitting device was prepared by using mCP (1,3-bis (N-carbazolyl) benzene material as a host in the light emitting layer under the same process conditions as in Example 1 described above, The results are shown in Table 2 below.

Item
Voltage
[V] Current density
[mA / cm2] Current efficiency
Cd / A Power efficiency
[Lm / W] Quantum efficiency
[%] Luminance
[Cd / m2] Example 1 5.8 5.1 19.50 8.78 12.20 1000 Example 2 5.7 5.1 19.61 10.81 10.1 1000 Example 3 5.4 4.9 20.41 11.87 12.3 1000 Example 4 4.9 4.8 20.83 13.36 13.1 1000 Example 5 5.0 4.7 21.28 13.37 13.5 1000 Comparative Example 1 6.71 14.1 6.80 3.21 3.86 1000

As described above, an optimal embodiment has been disclosed in the drawings and specification. It will be apparent to those skilled in the art that various modifications and variations can be made in the present invention without departing from the spirit of the invention, The scope should be determined by the technical idea of the appended claims.

10: substrate
20: anode electrode
30: Hole injection layer
40: hole transport layer
50: light emitting layer
60: electron transport layer
70: electron injection layer
80: cathode electrode

Claims (13)

A phosphorescent host compound represented by the following formula (3):
(3)

Wherein each of R 1 and R 2 is independently a substituted or unsubstituted functional group and is a cyano group, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C14 aryl group, a substituted or unsubstituted N , A C4-C14 heteroaryl group having at least one heteroatom of O, S, wherein the substitution is such that at least one of the hydrogen atoms of the unsubstituted moiety is substituted with a halogen atom, a hydroxy group, a nitro group, C14 alkyl group, C2-C14 alkynyl group, C2-C14 alkynyl group, C6-C14 aryl group, C7-C14 alkyl group, An arylalkyl group of C2-C14, a heteroaryl group of C2-C14, or a C3-C14 heteroalkyl group,
Each of R 3 to R 6 is independently a substituted or unsubstituted functional group selected from the group consisting of hydrogen, a cyano group, a hydroxyl group, a thiol group, a halogen atom, a substituted or unsubstituted C 1 -C 14 alkyl group, a substituted or unsubstituted C 1 -C 14 alkoxy group , A substituted or unsubstituted C2-C14 alkenyl group, a substituted or unsubstituted C6-C14 aryl group, a substituted or unsubstituted C6-C14 arylalkyl group, a substituted or unsubstituted C6-C14 aryloxy group, A substituted or unsubstituted C2-C14 heteroaryl group, a substituted or unsubstituted C2-C14 heteroarylalkyl group, a substituted or unsubstituted C2-C14 heteroaryloxy group, a substituted or unsubstituted C5- A substituted or unsubstituted C2-C14 heterocycloalkyl group, a substituted or unsubstituted C1-C14 alkylcarbonyl group, a substituted or unsubstituted C7-C14 arylcarbonyl group or a C1-C14 alkylthio group, The groups adjacent to each other among the functional groups of R 3 to R 6 are And it may form a ring in combination.
A phosphorescent host compound represented by the following formula (4):
Formula 4

Wherein each of R 1 and R 2 is independently a substituted or unsubstituted functional group and is a cyano group, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C14 aryl group, a substituted or unsubstituted N , A C4-C14 heteroaryl group having at least one heteroatom of O, S, wherein the substitution is such that at least one of the hydrogen atoms of the unsubstituted moiety is substituted with a halogen atom, a hydroxy group, a nitro group, C14 alkyl group, C2-C14 alkynyl group, C2-C14 alkynyl group, C6-C14 aryl group, C7-C14 alkyl group, An arylalkyl group of C2-C14, a heteroaryl group of C2-C14, or a C3-C14 heteroalkyl group,
Each of R 3 to R 6 is independently a substituted or unsubstituted functional group selected from the group consisting of hydrogen, a cyano group, a hydroxyl group, a thiol group, a halogen atom, a substituted or unsubstituted C 1 -C 14 alkyl group, a substituted or unsubstituted C 1 -C 14 alkoxy group , A substituted or unsubstituted C2-C14 alkenyl group, a substituted or unsubstituted C6-C14 aryl group, a substituted or unsubstituted C6-C14 arylalkyl group, a substituted or unsubstituted C6-C14 aryloxy group, A substituted or unsubstituted C2-C14 heteroaryl group, a substituted or unsubstituted C2-C14 heteroarylalkyl group, a substituted or unsubstituted C2-C14 heteroaryloxy group, a substituted or unsubstituted C5- A substituted or unsubstituted C2-C14 heterocycloalkyl group, a substituted or unsubstituted C1-C14 alkylcarbonyl group, a substituted or unsubstituted C7-C14 arylcarbonyl group or a C1-C14 alkylthio group, The groups adjacent to each other among the functional groups of R 3 to R 6 are And it may form a ring in combination.
A phosphorescent host compound represented by the following formula (5): < EMI ID =
Formula 5

Wherein each of R 1 and R 2 is independently a substituted or unsubstituted functional group and is a cyano group, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C14 aryl group, a substituted or unsubstituted N , A C4-C14 heteroaryl group having at least one heteroatom of O, S, wherein the substitution is such that at least one of the hydrogen atoms of the unsubstituted moiety is substituted with a halogen atom, a hydroxy group, a nitro group, C14 alkyl group, C2-C14 alkynyl group, C2-C14 alkynyl group, C6-C14 aryl group, C7-C14 alkyl group, An arylalkyl group of C2-C14, a heteroaryl group of C2-C14, or a C3-C14 heteroalkyl group,
Each of R 3 to R 6 is independently a substituted or unsubstituted functional group selected from the group consisting of hydrogen, a cyano group, a hydroxyl group, a thiol group, a halogen atom, a substituted or unsubstituted C 1 -C 14 alkyl group, a substituted or unsubstituted C 1 -C 14 alkoxy group , A substituted or unsubstituted C2-C14 alkenyl group, a substituted or unsubstituted C6-C14 aryl group, a substituted or unsubstituted C6-C14 arylalkyl group, a substituted or unsubstituted C6-C14 aryloxy group, A substituted or unsubstituted C2-C14 heteroaryl group, a substituted or unsubstituted C2-C14 heteroarylalkyl group, a substituted or unsubstituted C2-C14 heteroaryloxy group, a substituted or unsubstituted C5- A substituted or unsubstituted C2-C14 heterocycloalkyl group, a substituted or unsubstituted C1-C14 alkylcarbonyl group, a substituted or unsubstituted C7-C14 arylcarbonyl group or a C1-C14 alkylthio group, The groups adjacent to each other among the functional groups of R 3 to R 6 are And it may form a ring in combination.
A phosphorescent host compound represented by Formula 7:
Formula 7

Wherein each of R 1 and R 2 is independently a substituted or unsubstituted functional group and is a cyano group, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C14 aryl group, a substituted or unsubstituted N , A C4-C14 heteroaryl group having at least one heteroatom of O, S, wherein the substitution is such that at least one of the hydrogen atoms of the unsubstituted moiety is substituted with a halogen atom, a hydroxy group, a nitro group, C14 alkyl group, C2-C14 alkynyl group, C2-C14 alkynyl group, C6-C14 aryl group, C7-C14 alkyl group, An arylalkyl group of C2-C14, a heteroaryl group of C2-C14, or a C3-C14 heteroalkyl group,
Each of R 3 to R 6 is independently a substituted or unsubstituted functional group selected from the group consisting of hydrogen, a cyano group, a hydroxyl group, a thiol group, a halogen atom, a substituted or unsubstituted C 1 -C 14 alkyl group, a substituted or unsubstituted C 1 -C 14 alkoxy group , A substituted or unsubstituted C2-C14 alkenyl group, a substituted or unsubstituted C6-C14 aryl group, a substituted or unsubstituted C6-C14 arylalkyl group, a substituted or unsubstituted C6-C14 aryloxy group, A substituted or unsubstituted C2-C14 heteroaryl group, a substituted or unsubstituted C2-C14 heteroarylalkyl group, a substituted or unsubstituted C2-C14 heteroaryloxy group, a substituted or unsubstituted C5- A substituted or unsubstituted C2-C14 heterocycloalkyl group, a substituted or unsubstituted C1-C14 alkylcarbonyl group, a substituted or unsubstituted C7-C14 arylcarbonyl group or a C1-C14 alkylthio group, The groups adjacent to each other among the functional groups of R 3 to R 6 are And it may form a ring in combination.
A phosphorescent host compound represented by the following general formula (8):
8

Wherein each of R 1 and R 2 is independently a substituted or unsubstituted functional group and is a cyano group, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C14 aryl group, a substituted or unsubstituted N , A C4-C14 heteroaryl group having at least one heteroatom of O, S, wherein the substitution is such that at least one of the hydrogen atoms of the unsubstituted moiety is substituted with a halogen atom, a hydroxy group, a nitro group, C14 alkyl group, C2-C14 alkynyl group, C2-C14 alkynyl group, C6-C14 aryl group, C7-C14 alkyl group, An arylalkyl group of C2-C14, a heteroaryl group of C2-C14, or a C3-C14 heteroalkyl group,
Each of R 3 to R 6 is independently a substituted or unsubstituted functional group selected from the group consisting of hydrogen, a cyano group, a hydroxyl group, a thiol group, a halogen atom, a substituted or unsubstituted C 1 -C 14 alkyl group, a substituted or unsubstituted C 1 -C 14 alkoxy group , A substituted or unsubstituted C2-C14 alkenyl group, a substituted or unsubstituted C6-C14 aryl group, a substituted or unsubstituted C6-C14 arylalkyl group, a substituted or unsubstituted C6-C14 aryloxy group, A substituted or unsubstituted C2-C14 heteroaryl group, a substituted or unsubstituted C2-C14 heteroarylalkyl group, a substituted or unsubstituted C2-C14 heteroaryloxy group, a substituted or unsubstituted C5- A substituted or unsubstituted C2-C14 heterocycloalkyl group, a substituted or unsubstituted C1-C14 alkylcarbonyl group, a substituted or unsubstituted C7-C14 arylcarbonyl group or a C1-C14 alkylthio group, The groups adjacent to each other among the functional groups of R 3 to R 6 are And it may form a ring in combination.
A phosphorescent host compound represented by the following general formula (9):
Formula 9

Wherein each of R 1 and R 2 is independently a substituted or unsubstituted functional group and is a cyano group, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C14 aryl group, a substituted or unsubstituted N , A C4-C14 heteroaryl group having at least one heteroatom of O, S, wherein the substitution is such that at least one of the hydrogen atoms of the unsubstituted moiety is substituted with a halogen atom, a hydroxy group, a nitro group, C14 alkyl group, C2-C14 alkynyl group, C2-C14 alkynyl group, C6-C14 aryl group, C7-C14 alkyl group, An arylalkyl group of C2-C14, a heteroaryl group of C2-C14, or a C3-C14 heteroalkyl group,
Each of R 3 to R 6 is independently a substituted or unsubstituted functional group selected from the group consisting of hydrogen, a cyano group, a hydroxyl group, a thiol group, a halogen atom, a substituted or unsubstituted C 1 -C 14 alkyl group, a substituted or unsubstituted C 1 -C 14 alkoxy group , A substituted or unsubstituted C2-C14 alkenyl group, a substituted or unsubstituted C6-C14 aryl group, a substituted or unsubstituted C6-C14 arylalkyl group, a substituted or unsubstituted C6-C14 aryloxy group, A substituted or unsubstituted C2-C14 heteroaryl group, a substituted or unsubstituted C2-C14 heteroarylalkyl group, a substituted or unsubstituted C2-C14 heteroaryloxy group, a substituted or unsubstituted C5- A substituted or unsubstituted C2-C14 heterocycloalkyl group, a substituted or unsubstituted C1-C14 alkylcarbonyl group, a substituted or unsubstituted C7-C14 arylcarbonyl group or a C1-C14 alkylthio group, The groups adjacent to each other among the functional groups of R 3 to R 6 are And it may form a ring in combination.
A phosphorescent host compound represented by Formula 10 below:
10

Wherein each of R 1 and R 2 is independently a substituted or unsubstituted functional group and is a cyano group, a substituted or unsubstituted C1 to C6 alkyl group, a substituted or unsubstituted C6 to C14 aryl group, a substituted or unsubstituted N , A C4-C14 heteroaryl group having at least one heteroatom of O, S, wherein the substitution is such that at least one of the hydrogen atoms of the unsubstituted moiety is substituted with a halogen atom, a hydroxy group, a nitro group, C14 alkyl group, C2-C14 alkynyl group, C2-C14 alkynyl group, C6-C14 aryl group, C7-C14 alkyl group, An arylalkyl group of C2-C14, a heteroaryl group of C2-C14, or a C3-C14 heteroalkyl group,
Each of R 3 to R 6 is independently a substituted or unsubstituted functional group selected from the group consisting of hydrogen, a cyano group, a hydroxyl group, a thiol group, a halogen atom, a substituted or unsubstituted C 1 -C 14 alkyl group, a substituted or unsubstituted C 1 -C 14 alkoxy group , A substituted or unsubstituted C2-C14 alkenyl group, a substituted or unsubstituted C6-C14 aryl group, a substituted or unsubstituted C6-C14 arylalkyl group, a substituted or unsubstituted C6-C14 aryloxy group, A substituted or unsubstituted C2-C14 heteroaryl group, a substituted or unsubstituted C2-C14 heteroarylalkyl group, a substituted or unsubstituted C2-C14 heteroaryloxy group, a substituted or unsubstituted C5- A substituted or unsubstituted C2-C14 heterocycloalkyl group, a substituted or unsubstituted C1-C14 alkylcarbonyl group, a substituted or unsubstituted C7-C14 arylcarbonyl group or a C1-C14 alkylthio group, The groups adjacent to each other among the functional groups of R 3 to R 6 are And it may form a ring in combination.
A compound for a phosphorescent host is any one selected from the compounds represented by the following formulas.

,

or

A compound for a phosphorescent host is any one selected from the compounds represented by the following formulas.

,

or

A phosphorescent host compound which is a compound represented by the following formula.

An organic electroluminescent device comprising an organic film between a pair of electrodes, wherein the organic film comprises a compound for a phosphorescent host according to any one of claims 1 to 10.
12. The method of claim 11,
Wherein the organic layer is a light emitting layer.

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