KR20170022438A - Organic compound for optoelectronic device and organic optoelectronic device and display device - Google Patents

Organic compound for optoelectronic device and organic optoelectronic device and display device Download PDF

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KR20170022438A
KR20170022438A KR1020150117410A KR20150117410A KR20170022438A KR 20170022438 A KR20170022438 A KR 20170022438A KR 1020150117410 A KR1020150117410 A KR 1020150117410A KR 20150117410 A KR20150117410 A KR 20150117410A KR 20170022438 A KR20170022438 A KR 20170022438A
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장춘근
유은선
정성현
김보형
류동완
신창주
조영경
김창우
정주연
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삼성에스디아이 주식회사
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    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
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Abstract

A compound for an organic optoelectronic device represented by the general formula (I), an organic optoelectronic device using the same, and a display device including the organic optoelectronic device.
Details of the above formula (I) are as defined in the specification.

Description

TECHNICAL FIELD [0001] The present invention relates to an organic electroluminescent device,

A compound for an organic optoelectronic device, an organic optoelectronic device and a display device.

An organic optoelectronic device is an element capable of converting electrical energy to optical energy.

Organic optoelectronic devices can be roughly classified into two types according to the operating principle. One is an optoelectronic device in which an exciton formed by light energy is separated into an electron and a hole, the electron and hole are transferred to different electrodes to generate electric energy, and the other is a voltage / Emitting device that generates light energy from energy.

Examples of organic optoelectronic devices include organic optoelectronic devices, organic light emitting devices, organic solar cells, and organic photo conductor drums.

In recent years, organic light emitting diodes (OLEDs) have attracted considerable attention due to the demand for flat panel display devices. The organic light emitting diode is a device for converting electrical energy into light by applying an electric current to the organic light emitting material, and usually has an organic layer inserted between an anode and a cathode. The organic layer may include a light emitting layer and an optional auxiliary layer. The auxiliary layer may include, for example, a hole injecting layer, a hole transporting layer, an electron blocking layer, an electron transporting layer, And a hole blocking layer.

The performance of the organic light emitting device is greatly influenced by the characteristics of the organic layer, and the organic layer is highly affected by the organic material contained in the organic layer.

In particular, in order for the organic light emitting device to be applied to a large-sized flat panel display device, it is necessary to develop an organic material capable of increasing the mobility of holes and electrons and increasing the electrochemical stability.

High efficiency, long life, and the like.

An organic optoelectronic device including the compound, and a display device including the organic optoelectronic device.

According to one embodiment, there is provided a compound for an organic optoelectronic device represented by the following general formula (I).

(I)

Figure pat00001

In the above formula (I)

R 1 and R 2 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C30 alkyl group; A C6 to C30 aryl group, a C2 to C30 heterocyclic group, or a combination thereof; Or a combination thereof,

At least one of R 1 and R 2 is an amine group substituted with a C6 to C30 aryl group, a C2 to C30 heterocyclic group, or a combination thereof,

Unless otherwise defined herein, "substituted" means that at least one hydrogen is replaced by a substituent selected from the group consisting of deuterium, a halogen group, a hydroxyl group, C1 to C40 silyl groups, C1 to C30 alkyl groups, C1 to C10 alkylsilyl groups, C3 to C30 cycloalkyl groups, A C 2 to C 30 heterocycloalkyl group, a C 6 to C 30 aryl group, a C 2 to C 30 heterocyclic group, a C 1 to C 20 alkoxy group, a C 1 to C 10 trifluoroalkyl group or a cyano group.

According to another embodiment of the present invention, there is provided a light emitting device comprising: an anode and a cathode opposing each other; and at least one organic layer positioned between the anode and the cathode, wherein the organic layer comprises a light emitting layer and a hole injecting layer, a hole transporting layer, At least one auxiliary layer selected from a hole transporting layer, a hole transporting layer, a hole transporting layer, a hole transporting layer, a hole transporting layer, an electron transporting layer, an electron injecting layer and a hole blocking layer.

According to another embodiment, there is provided a display device including the organic optoelectronic device.

High-efficiency long-lived organic optoelectronic devices can be realized.

1 and 2 are sectional views showing an organic light emitting device according to an embodiment, respectively.

Hereinafter, embodiments of the present invention will be described in detail. However, it should be understood that the present invention is not limited thereto, and the present invention is only defined by the scope of the following claims.

As used herein, "substituted" means that at least one hydrogen is substituted with one or more substituents selected from the group consisting of deuterium, halogen, hydroxyl, C1 to C40 silyl, C1 to C30 alkyl, C1 to C10 alkylsilyl, C3 to C30 cycloalkyl, Means a group substituted with a cycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heterocyclic group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, or a cyano group.

A substituted or unsubstituted C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C3 to C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 An aryl group, a C6 to C30 heterocyclic group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group or a cyano group may be fused to form a ring. For example, the substituted C6 to C30 aryl group may be fused with another adjacent substituted C6 to C30 aryl group to form a substituted or unsubstituted fluorene ring.

Means one to three heteroatoms selected from the group consisting of N, O, S, P and Si in one functional group, and the remainder being carbon unless otherwise defined .

As used herein, the term "alkyl group" means an aliphatic hydrocarbon group, unless otherwise defined. The alkyl group may be a "saturated alkyl group" which does not contain any double or triple bonds.

The alkyl group may be an alkyl group of C1 to C30. More specifically, the alkyl group may be a C1 to C20 alkyl group or a C1 to C10 alkyl group. For example, C1 to C4 alkyl groups mean that from 1 to 4 carbon atoms are included in the alkyl chain and include methyl, ethyl, propyl, iso-propyl, n-butyl, iso-butyl, sec- Indicating that they are selected from the group.

Specific examples of the alkyl group include a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, hexyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, And the like.

As used herein, the term " aryl group "is intended to encompass groups having one or more hydrocarbon aromatic moieties, in which all the elements of the hydrocarbon aromatic moiety have a p-orbital, Such as a biphenyl group, a terphenyl group, a quaterphenyl group, and the like, which include two or more hydrocarbon aromatic moieties including a phenyl group, a naphthyl group, and the like, in which two or more hydrocarbon aromatic moieties are connected through a sigma bond, May also include non-aromatic fused rings fused directly or indirectly. For example, a fluorenyl group and the like.

The aryl groups include monocyclic, polycyclic or fused ring polycyclic (i. E., Rings that divide adjacent pairs of carbon atoms) functional groups. For example, the aryl group means a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a klycenyl group, and the like.

As used herein, the term " heterocyclic group "is a superordinate concept including a heteroaryl group, and includes N, O, and S substituents in the ring compound such as an aryl group, a cycloalkyl group, a fused ring thereof, Means at least one heteroatom selected from the group consisting of S, P and Si. When the heterocyclic group is a fused ring, the heterocyclic group or the ring may include one or more heteroatoms.

As used herein, the term " heteroaryl group "means that at least one heteroatom selected from the group consisting of N, O, S, P and Si is contained in the aryl group instead of carbon (C). Two or more heteroaryl groups may be directly connected through a sigma bond, or when the C2 to C60 heteroaryl group includes two or more rings, two or more rings may be fused with each other. When the heteroaryl group is a fused ring, it may contain 1 to 3 heteroatoms in each ring.

More specifically, the substituted or unsubstituted C6 to C30 aryl group and / or the substituted or unsubstituted C2 to C30 heterocyclic group may be substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthra A substituted or unsubstituted phenanthryl group, a substituted or unsubstituted naphthacenyl group, a substituted or unsubstituted pyrenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted p-terphenyl group, a substituted or unsubstituted naphthacenyl group, A substituted or unsubstituted aryl group, a substituted m-terphenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted furanyl group , A substituted or unsubstituted thiophenyl group, a substituted or unsubstituted pyrrolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted imidazolyl group, a substituted or unsubstituted triazolyl group, a substituted or unsubstituted pyrazolyl group, A substituted or unsubstituted thiazolyl group, a substituted or unsubstituted oxadiazolyl group, a substituted or unsubstituted thiadiazolyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group , A substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted benzothiophenyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted benzothiophenyl group, A substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinolinyl group, a substituted or unsubstituted quinolinyl group, Substituted or unsubstituted quinoxalinyl groups, substituted or unsubstituted naphthyridinyl groups, substituted or unsubstituted benzoxazinyl groups, substituted or unsubstituted benzthiazinyl groups, substituted or unsubstituted quinoxalinyl groups, substituted or unsubstituted quinoxalinyl groups, A substituted or unsubstituted phenanthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted phenothiazyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group , A substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted benzothiophene pyrimidinyl group, a substituted or unsubstituted benzothiophene pyridyl group, a substituted or unsubstituted benzofuranpyri A substituted or unsubstituted pyrazolyl group, a substituted pyrazolyl group, a substituted pyrazolyl group, a substituted pyrazolyl group, a substituted pyrazolyl group, a substituted pyrazolyl group, a substituted or unsubstituted pyrazolyl group, a substituted or unsubstituted benzopyranyl group, A substituted or unsubstituted thiazoloquinolinyl group, a substituted or unsubstituted oxazolinoquinolinyl group, or a combination thereof, but is not limited thereto.

In the present specification, a single bond means a bond directly connected to a carbon atom or a hetero atom other than carbon. Specifically, L means a single bond, meaning that the substituent connected to L is directly connected to the center core do. That is, in the present specification, a single bond does not mean methylene or the like via carbon.

In the present specification, the hole property refers to a property of forming holes by donating electrons when an electric field is applied, and has a conduction property along the HOMO level so that the injection of holes formed in the anode into the light emitting layer, Quot; refers to the property of facilitating the movement of the hole formed in the light emitting layer to the anode and the movement of the hole in the light emitting layer.

In addition, the electron characteristic refers to a characteristic that electrons can be received when an electric field is applied. The electron characteristic has a conduction characteristic along the LUMO level so that electrons formed in the cathode are injected into the light emitting layer, electrons formed in the light emitting layer migrate to the cathode, It is a characteristic that facilitates movement.

The compounds for organic optoelectronic devices according to one embodiment will be described below.

The compound for organic optoelectronic devices according to one embodiment is represented by the following formula (I).

(I)

Figure pat00002

In the above formula (I)

R 1 and R 2 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C30 alkyl group; A C6 to C30 aryl group, a C2 to C30 heterocyclic group, or a combination thereof; Or a combination thereof,

At least one of R 1 and R 2 is an amine group substituted with a C6 to C30 aryl group, a C2 to C30 heterocyclic group, or a combination thereof,

Unless otherwise defined herein, "substituted" means that at least one hydrogen is replaced by a substituent selected from the group consisting of deuterium, a halogen group, a hydroxyl group, C1 to C40 silyl groups, C1 to C30 alkyl groups, C1 to C10 alkylsilyl groups, C3 to C30 cycloalkyl groups, A C 2 to C 30 heterocycloalkyl group, a C 6 to C 30 aryl group, a C 2 to C 30 heterocyclic group, a C 1 to C 20 alkoxy group, a C 1 to C 10 trifluoroalkyl group or a cyano group.

The compound for organic optoelectronic devices represented by the above-mentioned formula (I) is a bulky phenyl compound in which the phenyl group in the core is 5-substituted. In particular, the phenyl group substituted at the position adjacent to the non-substituted position in the core phenyl group is substituted with a C6 to C30 aryl group, a C2 to C30 heterocyclic group, or a combination thereof at the meta position, i.e., at least one of R 1 and R 2 . Lt; / RTI >

The compound for the organic optoelectronic device has a molecular intermolecular interaction due to the steric hindrance of the molecule itself due to five phenyl substituents, so that the crystallization is inhibited and the yield of producing the organic EL device can be improved. In addition, A substituent group is contained in the meta position of the substituted phenyl substituent at the position adjacent to the non-substituted position, that is, the substituent is included in R 1 or R 2 , the relative molecular structure is relatively flexible relative to the compound containing the substituent at the para position, It is possible to obtain an advantageous effect in terms of efficiency.

Further, by including an amine group substituted at the R 1 and R 2 positions with a C6 to C30 aryl group, a C2 to C30 heterocyclic group, or a combination thereof, hole transportability can be improved, and the driving voltage can be improved thereby .

According to an embodiment of the present invention, any one of R 1 and R 2 may be an amine group substituted with a C6 to C30 aryl group, a C2 to C30 heterocyclic group, or a combination thereof, and the remainder may be hydrogen.

For example, represented by the following formula (I-1).

[Formula (I-1)

Figure pat00003

In the above formula (I-1)

L 1 and L 2 are each independently a single bond, a C 6 to C 30 arylene group, a C 2 to C 30 heteroarylene group, or a combination thereof,

R a and R b are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,

Here, "substituted" is as described above.

According to an embodiment of the present invention, R a and R b each independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted o-biphenyl group, a substituted or unsubstituted m-biphenyl group, A substituted or unsubstituted naphthyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted naphthyl group, A dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a combination thereof.

More specifically, it may be selected from the groups listed in Group I below, but is not limited thereto.

[Group I]

Figure pat00004

Figure pat00005

In the above group I, * is a connecting point connecting with L 1 or L 2 of the above formula (I-1).

In the meantime, L 1 and L 2 may specifically be a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group.

The compound for an organic optoelectronic device may be, for example, a compound listed in the following Group II, but is not limited thereto.

[Group II]

[1] [2] [3] [4]

Figure pat00006

[5] [6] [7] [8]

Figure pat00007

[9] [10] [11] [12]

Figure pat00008

[13] [14] [15] [16]

Figure pat00009

[17] 18 [19] [20]

Figure pat00010

[21] [22] [23]

Figure pat00011

[24] [25] [26]

Figure pat00012

[27] [28] [29]

Figure pat00013

[30] [31] [32]

Figure pat00014

[33] [34] [35]

Figure pat00015

[36] [37] [38]

Figure pat00016

[39] [40] [41]

Figure pat00017

[42] [43] [44]

Figure pat00018

[45] 46 [47]

Figure pat00019

[48] 49 [50]

Figure pat00020

[51] 52 [53]

Figure pat00021

[54] [55] [56]

Figure pat00022

[57] [58] [59]

Figure pat00023

[60] 61 [62] [63]

Figure pat00024

[64] 65 [66] [67]

Figure pat00025

[68] 69 [70] [71]

Figure pat00026

[72] [73] [74] [75]

Figure pat00027

[76] 77 [78] [79]

Figure pat00028

[80] 81 [82] [83]

Figure pat00029

[84] 85 [86] [87]

Figure pat00030

[88] 89 [90] [91]

Figure pat00031

[92] 93 [94] [95]

Figure pat00032

[96] [97] [98] [99]

Figure pat00033

[100] [101] [102] [103]

Figure pat00034

[104] [105] [106] [107]

Figure pat00035

[108] [109] [110] [111]

Figure pat00036

[112] [113] [114] [115]

Figure pat00037

[116] 117 [118] [119]

Figure pat00038

[120] [121] [122] [123]

Figure pat00039

[124] 125 [126] [127]

Figure pat00040

[128] [129] [130] [131]

Figure pat00041

[132] [133] [134] [135]

Figure pat00042

[136] [137] [138] [139]

Figure pat00043

[140] [141] [142] [143]

Figure pat00044

[144] 145 [146] [147]

Figure pat00045

[148] 149 [150] [151]

Figure pat00046

[152] [153] [154] [155]

Figure pat00047

[156] [157] [158] [159]

Figure pat00048

[160] [161] [162] [163]

Figure pat00049

[164] [165] [166] [167]

Figure pat00050

[168] [169] [170] [171]

Figure pat00051

[172] [173] [174] [175]

Figure pat00052

[176] [177] [178] [179]

Figure pat00053

[180] [181] [182] [183]

Figure pat00054

[184] [185] [186] [187]

Figure pat00055

[188] [189] [190]

Figure pat00056
.

Hereinafter, the organic optoelectronic device to which the compound for an organic optoelectronic device described above is applied will be described.

The organic optoelectronic device is not particularly limited as long as it is an element capable of converting electric energy and optical energy. Examples of the organic optoelectronic device include organic light emitting devices, organic solar cells, and organic photoconductor drums.

The organic optoelectronic device includes an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode. The organic layer includes a light emitting layer, a hole injecting layer, a hole transporting layer, , At least one auxiliary layer selected from an electron injection layer and a hole blocking layer, and the auxiliary layer includes the above-mentioned compound for an organic optoelectronic device.

Here, an organic light emitting device, which is an example of an organic optoelectronic device, will be described with reference to the drawings.

1 and 2 are cross-sectional views illustrating an organic light emitting device according to an embodiment.

1, an organic optoelectronic device 100 according to an embodiment includes an anode 120 and a cathode 110 facing each other, and an organic layer 105 located between the anode 120 and the cathode 110 .

The anode 120 may be made of a conductor having a high work function to facilitate, for example, hole injection, and may be made of, for example, a metal, a metal oxide, and / or a conductive polymer. The anode 120 is made of a metal such as nickel, platinum, vanadium, chromium, copper, zinc, gold, or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of ZnO and Al or a metal and an oxide such as SnO 2 and Sb; Conductive polymers such as poly (3-methylthiophene), poly (3,4- (ethylene-1,2-dioxy) thiophene), polypyrrole and polyaniline, It is not.

The cathode 110 may be made of a conductor having a low work function, for example, to facilitate electron injection, and may be made of, for example, a metal, a metal oxide, and / or a conductive polymer. The cathode 110 is made of a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, lead, cesium, barium or the like or an alloy thereof; Layer structure materials such as LiF / Al, LiO 2 / Al, LiF / Ca, LiF / Al and BaF 2 / Ca.

The organic layer 105 includes a light emitting layer 130.

The light emitting layer 130 may include, for example, a compound alone or a mixture of two kinds thereof. When the two types are mixed and included, they may be included in the form of, for example, a host and a dopant. The host may be, for example, a phosphorescent host or a fluorescent host.

The dopant may be an inorganic, organic, or organic compound and may be selected from among known dopants.

Referring to FIG. 2, the organic light emitting diode 200 further includes a hole-assist layer 140 in addition to the light-emitting layer 130. The hole auxiliary layer 140 can further enhance hole injection and / or hole mobility between the anode 120 and the light emitting layer 130 and block electrons. The hole-assist layer 140 may be, for example, a hole transport layer, a hole injection layer, and / or an electron blocking layer, and may include at least one layer. The above-described compound for an organic optoelectronic device can be included in the hole-assist layer 140.

1 or 2 may further include an electron injection layer, an electron transport layer, an electron transporting auxiliary layer, a hole transporting layer, a hole transporting auxiliary layer, a hole injecting layer, or a combination layer thereof have. The above-described compound for an organic optoelectronic device can be included in the hole transporting auxiliary layer.

The light emitting layer 130 and the hole transporting layer may be adjacent to each other.

The organic light emitting devices 100 and 200 may be formed by forming an anode or a cathode on a substrate and then performing a dry deposition method such as evaporation, sputtering, plasma plating, and ion plating; Or a wet film formation method such as spin coating, dipping or flow coating, and then forming a cathode or anode on the organic layer.

The above-mentioned compound for an organic optoelectronic device can be included as a fluorescent material.

The organic light emitting device described above can be applied to an organic light emitting display.

Hereinafter, compounds and organic light emitting devices according to one embodiment of the present invention will be described in more detail with reference to the following Synthesis Examples and Examples, but the present invention is not limited to the following Synthesis Examples and Examples. In the following Synthesis Examples, the amounts of 'B' and 'A' used in the expression "B" was used in place of "A" were the same on the molar equivalent basis.

The starting materials and reaction materials used in the examples and the synthesis examples are commercially available from Sigma-Aldrich, TCI, AAA Chemistry, etc., unless otherwise specified, or those described in references (J. Org. Chem. 40, 3514-3518 (1975).

The compound of the above formula (I) presented as a more specific example of the compound for organic optoelectronic devices of the present invention was synthesized through the following reaction schemes.

Synthetic example  1: Synthesis of compound 1

[Reaction Scheme 1]

Figure pat00057

Step 1: Synthesis of intermediate I-1

Bromo-3-iodobenzene (60.7 g, 214.5 mmol) and (1,1'-bis (diphenylphosphine) ferrocene) dichloropalladium (II) (7.8 g, 10.7 mmol), copper iodide (1.22 g, 6.43 mmol), triethylamine (86.8 g, 858 mmol) and 800 mL of tetrahydrofuran. Trimethylsilylacetylene (23.6 g, 240.2 mmol) was added dropwise thereto, followed by stirring at room temperature for 3 hours. The reaction was filtered and the solvent was removed, and then the compound was purified by column chromatography to obtain 52 g (96%) of Intermediate I-1.

Step 2: Synthesis of Intermediate I-2

The intermediate I-1 (52 g, 205.36 mmol) was dissolved in methanol (400 mL), and then potassium carbonate (28.4 g, 205.36 mmol) was slowly added dropwise to the reactor. After stirring for about 30 minutes, the solution was filtered and the solvent was removed. The reaction product was dissolved in ethyl acetate and washed twice with distilled water. The solvent was removed to give 37 g (100%) of intermediate I-2.

Step 3: Synthesis of Intermediate I-3

Intermediate I-2 (20 g, 114.44 mmol) and tetraphenylcyclopentadienone (40 g, 104.04 mmol) were dissolved in 100 mL of xylene and refluxed for 3 hours. The reaction was poured into 500 mL of methanol to terminate the reaction, and 40 g (72%) of Intermediate I-3 was obtained by filtering the solid.

Step 4: Synthesis of Compound 1

(10.0 g, 18.6 mmol) was added to a solution of 1.07 g of bisdibenzylidene acetone palladium (0), 1.13 g of tri-t-butylphosphine and 2.14 g of sodium t-butoxide in 75 ml of toluene in a nitrogen atmosphere And the mixture was refluxed by heating for 3 hours. After completion of the reaction, the reaction solution was filtered once at a high temperature, extracted twice with brine, and then the organic layer was dried and concentrated. The concentrated solution was added dropwise to 400 ml of methanol to obtain crystals. The crystals were collected and filtered. The thus obtained residue was purified by column chromatography to obtain 10.7 g (74%) of Compound 1.

LC Mass (calculated: 777.99 g / mol, measured: M + H + = 776.85 g / mol)

Comparative Synthesis Example 1

(Hereinafter referred to as "Para-1") was synthesized by referring to the method described in JP2007-0079680.

Figure pat00058

(Analysis and Characterization of the Prepared Compound)

The measured glass transition temperatures and the energy levels of each material calculated using the Gaussian 09 method using a supercomputer GAIA (IBM power 6) are shown in Table 1 below.

compound HOMO (eV) (calculated) LUMO (eV) (calculated value) Glass transition temperature
(Tg, ° C) Compound 1 4.87 0.94 126 Para-1 4.84 0.94 135

Referring to Table 1, the electron energy levels according to the quantum chemistry calculation of Compound 1 and Para-1, which are comparative substances, are almost the same and the glass transition temperature is a high temperature suitable for both organic light emitting devices. However, 1, it can be confirmed that it has a glass transition temperature as low as about 10 ° C. From the glass transition temperature, the molecular structure of Compound 1 can be more flexible.

Fabrication of organic light emitting device

Example 1: Preparation of blue organic light emitting device

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 washed 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, and then the substrate was transferred to a vacuum deposition machine. The prepared ITO transparent electrode was used as an anode to form a 4,4'-bis [N- [4- {N, N-bis (3-methylphenyl) amino} -phenyl] -N-phenylamino] biphenyl ) Was vacuum-deposited to form a hole injection layer having a thickness of 600 Å. Subsequently, HT-1 was vacuum deposited to form a 250 Å thick hole transport layer. A hole transporting auxiliary layer having a thickness of 50 A was formed on the hole transporting layer by vacuum deposition using the compound 1 prepared in Synthesis Example 1. (2-naphthyl) anthracene (ADN) was used as a host on top of the hole transporting layer and 2,5,8,11-tetra (tert-butyl) perylene %, And a 250 Å thick light emitting layer was formed by vacuum evaporation.

Thereafter, Alq 3 was vacuum-deposited on the light emitting layer to form an electron transporting layer 250 Å thick. LiF 10 Å and Al 1000 Å were sequentially vacuum-deposited on the electron transport layer to form a cathode, thereby preparing an organic light emitting device.

The organic light emitting device has a structure having a multilayer organic thin film layer,

(250 ANGSTROM) / EML [ADN: TBPe = 97: 3] (250 ANGSTROM) / hole transporting auxiliary layer (50 ANGSTROM) / HT-1 (250 ANGSTROM / DNTPD / 600 ANGSTROM) / LiF (10 ANGSTROM) / Alq3 ITO (1500 Å).

Comparative Example 1

An organic luminescent device was produced in the same manner as in Example 1, except that the compound Para-1 of Comparative Synthesis Example 1 was used instead of the compound 1 of Synthesis Example 1.

The structures of DNTPD, HT-1, HT-2, Alq 3 , ADN, and TBPe used in the organic light emitting device are as follows.

Figure pat00059

evaluation

The changes in the current density, the luminance, and the luminous efficiency of the organic light emitting device according to Example 1 and Comparative Example 1 were measured according to the voltage.

The specific measurement method is as follows, and the results are shown in Table 2.

(1) Measurement of change in current density with voltage change

For the organic light emitting device manufactured, the current flowing through the unit device was measured using a current-voltmeter (Keithley 2400) while raising the voltage from 0 V to 10 V, and the measured current value was divided by the area to obtain the result.

(2) Measurement of luminance change according to voltage change

For the organic light-emitting device manufactured, luminance was measured using a luminance meter (Minolta Cs-1000A) while increasing the voltage from 0 V to 10 V, and the result was obtained.

(3) Measurement of luminous efficiency

The current efficiency (cd / A) at the same current density (10 mA / cm 2 ) was calculated using the luminance, current density and voltage measured from the above (1) and (2).

(4) Measurement of driving voltage

The driving voltage of each device was measured at 15 mA / cm 2 using a current-voltage meter (Keithley 2400).

No. compound The driving voltage (V) Color (EL color) Efficiency (cd / A) The color coordinates (x, y) Example 1 Compound 1 4.76 Blue 6.6 0.132, 0.139 Comparative Example 1 Para-1 4.86 Blue 6.5 0.133, 0.145

Referring to Table 2, it can be seen that the driving voltage and efficiency characteristics of the organic light emitting device of Example 1 are improved as compared with the organic light emitting device of Comparative Example 1. [

This means that the substitution of an aryl group or an amine substituted with a heterocycle for a bulky phenyl compound has more favorable physical properties in the morphology in the substitution at the meta position than in the case of substitution at the para position, It can be seen that the hole transporting ability of Comparative Example 1 is improved.

It will be understood by those skilled in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present invention as defined by the following claims. As will be understood by those skilled in the art. It is therefore to be understood that the above-described embodiments are illustrative in all aspects and not restrictive.

100, 200: Organic light emitting device
105: organic layer
110: cathode
120: anode
130: light emitting layer
140: hole assist layer

Claims (11)

A compound for an organic optoelectronic device represented by the following formula (I):
(I)
Figure pat00060

In the above formula (I)
R 1 and R 2 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted C1 to C30 alkyl group; A C6 to C30 aryl group, a C2 to C30 heterocyclic group, or a combination thereof; Or a combination thereof,
At least one of R 1 and R 2 is an amine group substituted with a C6 to C30 aryl group, a C2 to C30 heterocyclic group, or a combination thereof,
The term "substituted" as used herein means an alkyl group having at least one hydrogen atom, To C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heterocyclic group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, or a cyano group. The method according to claim 1,
Wherein any one of R 1 and R 2 is an amine group substituted with a C6 to C30 aryl group, a C2 to C30 heterocyclic group, or a combination thereof, and the remainder is hydrogen. The method according to claim 1,
Wherein the compound represented by Formula (I) is represented by Formula (I-1): < EMI ID =
[Formula (I-1)
Figure pat00061

In the above formula (I-1)
L 1 and L 2 are each independently a single bond, a C 6 to C 30 arylene group, a C 2 to C 30 heteroarylene group, or a combination thereof,
R a and R b are each independently a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heterocyclic group, or a combination thereof,
The term "substituted" as used herein means that at least one hydrogen is replaced by a substituent selected from the group consisting of deuterium, a halogen group, a hydroxyl group, a C1 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C3 to C30 cycloalkyl group, a C2 to C30 heterocycloalkyl group , A C6 to C30 aryl group, a C2 to C30 heterocyclic group, a C1 to C20 alkoxy group, a C1 to C10 trifluoroalkyl group, or a cyano group. The method of claim 3,
R a and R b each independently represent a substituted or unsubstituted phenyl group, a substituted or unsubstituted o-biphenyl group, a substituted or unsubstituted m-biphenyl group, a substituted or unsubstituted p-biphenyl group, Substituted or unsubstituted m-terphenyl groups, substituted or unsubstituted p-terphenyl groups, substituted or unsubstituted naphthyl groups, substituted or unsubstituted dibenzofuranyl groups, substituted or unsubstituted naphthyl groups, A dibenzothiophene group, or a combination thereof. The method of claim 3,
Wherein R & lt ; a & gt ; and R < b & gt ; are each independently selected from the groups listed in the following Group I:
[Group I]
Figure pat00062

Figure pat00063

In the above group I, * is a connecting point connecting with L 1 or L 2 of the above formula (I-1). The method of claim 3,
Wherein L 1 and L 2 are each independently a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group. The method according to claim 1,
Wherein the compound is selected from the compounds listed in Group < RTI ID = 0.0 > II < / RTI &
[Group II]
[1] [2] [3] [4]
Figure pat00064

[5] [6] [7] [8]
Figure pat00065

[9] [10] [11] [12]
Figure pat00066

[13] [14] [15] [16]
Figure pat00067

[17] 18 [19] [20]
Figure pat00068

[21] [22] [23]
Figure pat00069

[24] [25] [26]
Figure pat00070

[27] [28] [29]
Figure pat00071

[30] [31] [32]
Figure pat00072

[33] [34] [35]
Figure pat00073

[36] [37] [38]
Figure pat00074

[39] [40] [41]
Figure pat00075

[42] [43] [44]
Figure pat00076

[45] 46 [47]
Figure pat00077

[48] 49 [50]
Figure pat00078

[51] 52 [53]
Figure pat00079

[54] [55] [56]
Figure pat00080

[57] [58] [59]
Figure pat00081

[60] 61 [62] [63]
Figure pat00082

[64] 65 [66] [67]
Figure pat00083

[68] 69 [70] [71]
Figure pat00084

[72] [73] [74] [75]
Figure pat00085

[76] 77 [78] [79]
Figure pat00086

[80] 81 [82] [83]
Figure pat00087

[84] 85 [86] [87]
Figure pat00088

[88] 89 [90] [91]
Figure pat00089

[92] 93 [94] [95]
Figure pat00090

[96] [97] [98] [99]
Figure pat00091

[100] [101] [102] [103]
Figure pat00092

[104] [105] [106] [107]
Figure pat00093

[108] [109] [110] [111]
Figure pat00094

[112] [113] [114] [115]
Figure pat00095

[116] 117 [118] [119]
Figure pat00096

[120] [121] [122] [123]
Figure pat00097

[124] 125 [126] [127]
Figure pat00098

[128] [129] [130] [131]
Figure pat00099

[132] [133] [134] [135]
Figure pat00100

[136] [137] [138] [139]
Figure pat00101

[140] [141] [142] [143]
Figure pat00102

[144] 145 [146] [147]
Figure pat00103

[148] 149 [150] [151]
Figure pat00104

[152] [153] [154] [155]
Figure pat00105

[156] [157] [158] [159]
Figure pat00106

[160] [161] [162] [163]
Figure pat00107

[164] [165] [166] [167]
Figure pat00108

[168] [169] [170] [171]
Figure pat00109

[172] [173] [174] [175]
Figure pat00110

[176] [177] [178] [179]
Figure pat00111

[180] [181] [182] [183]
Figure pat00112

[184] [185] [186] [187]
Figure pat00113

[188] [189] [190]
Figure pat00114
. Positive and negative facing each other, and
And at least one organic layer positioned between the anode and the cathode,
The organic layer includes at least one auxiliary layer selected from a light emitting layer and a hole injecting layer, a hole transporting layer, an electron blocking layer, an electron transporting layer, an electron injecting layer and a hole blocking layer,
Wherein the auxiliary layer comprises the compound for organic optoelectronic devices according to any one of claims 1 to 7. 9. The method of claim 8,
Wherein the auxiliary layer further comprises a hole transporting auxiliary layer adjacent to the light emitting layer,
Wherein the hole transporting auxiliary layer comprises the compound for the organic optoelectronic device. 9. The method of claim 8,
Wherein the compound for an organic optoelectronic device is included as a fluorescent material. 9. A display device comprising the organic electroluminescent device according to claim 8.
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CN104498025A (en) * 2015-01-21 2015-04-08 武汉大学 Polyphenyl benzene structured cyanogroup-containing luminescent molecule and preparation method and purpose thereof

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WO2019044542A1 (en) * 2017-08-28 2019-03-07 東レ株式会社 Compound, light-emitting element using same, display device, and lighting device
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