KR101648142B1 - Composition and organic optoelectric device and display device - Google Patents

Abstract

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상기 화학식 I 및 Ⅱ에서, X₁ 내지 X₄, R_1a 내지 R_5a, 및 R_1b 내지 R_5b는 명세서에서 정의한 바와 같다.A first host compound represented by the following formula (I) and a second host compound represented by the following formula (II), an organic optoelectronic device including the composition and a display device.
(I) < RTI ID = 0.0 > (II)

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In the above formulas (I) and (II), X ₁ to X ₄ , R _1a to R _5a , and R _1b to R _5b are as defined in the specification.

Description

Technical Field [0001] The present invention relates to a composition, an organic optoelectronic device,

Compositions, organic optoelectronic devices and display devices.

Organic optoelectronic devices are devices that can switch between electrical and 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.

One embodiment provides a composition for an organic optoelectronic device capable of implementing a high-efficiency and long-lived organic optoelectronic device.

Another embodiment provides an organic optoelectronic device comprising the composition.

Another embodiment provides a display device comprising the organic opto-electronic device.

According to one embodiment, there is provided a composition comprising a first host compound represented by formula (I) and a second host compound represented by formula (II):

(I) < RTI ID = 0.0 > (II)

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In the above formulas (I) and (II)

R _1a to R _5a each independently represent a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or A combination thereof,

R _1b to R _5b are each independently a substituted or unsubstituted C2 to C30 heteroaryl group containing at least one N except for a substituted or unsubstituted carbazolyl group,

X ₁ and X ₃ are each independently O, Se, S, SO, SO ₂ , PO or CO,

X ₂ and X ₄ are each independently CR _a R _b or SiR _c R _d ,

R _a to R _d each independently represent hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C3 to C30 heteroaryl amine A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkoxycarbonyl group, a substituted or unsubstituted C2 to C30 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C30 aryloxycarbonylamino group , A substituted or unsubstituted C1 to C30 sulfamoylamino group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, A substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C1 to C20 acylamino group, a substituted or unsubstituted C1 to C30 acyl group, a substituted or unsubstituted C1 to C20 acyloxy group, a substituted or unsubstituted C1 to C20 acylamino group, A substituted or unsubstituted C1 to C30 alkylthiol group, a substituted or unsubstituted C1 to C30 heterocyclic thiol group, a substituted or unsubstituted C6 to C30 arylthiol group, a substituted or unsubstituted C1 to C30 arylthiol group, A C1 to C30 heteroarylthiol group, a substituted or unsubstituted C1 to C30 ureide group, a halogen group, a halogen-containing group, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a ferrocenyl group or a combination thereof.

According to another embodiment, there is provided an organic optoelectronic device including an anode and a cathode facing each other, and at least one organic layer positioned between the anode and the cathode, wherein the organic layer comprises the composition.

According to another embodiment, there is provided a display device including the organic opto-electronic 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, unless otherwise defined, at least one of the substituents or at least one hydrogen in the compound is substituted with one or more substituents selected from the group consisting of deuterium, a halogen group, a hydroxy group, an amino group, a substituted or unsubstituted C1 to C30 amine group, a nitro group, A C1 to C30 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 aryl group, a C2 to C30 heteroaryl group, , A C1 to C10 trifluoroalkyl group such as a fluoro group or a trifluoromethyl group, or a cyano group.

A substituted or unsubstituted C1 to C20 amine group, a nitro group, a substituted or unsubstituted C3 to C40 silyl group, a C1 to C30 alkyl group, a C1 to C10 alkylsilyl group, a C3 to C10 alkylsulfinyl group, A C1 to C10 trifluoroalkyl group such as a C30 cycloalkyl group, a C3 to C30 heterocycloalkyl group, a C6 to C30 aryl group, a C2 to C30 heteroaryl group, a C1 to C20 alkoxy group, a fluoro group and a trifluoromethyl group; Two adjacent substituents 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 "means a substituent in which all the elements of the cyclic substituent have p-orbital, and these p-orbital forms a conjugation, and monocyclic, Fused ring polycyclic (i. E., Rings that divide adjacent pairs of carbon atoms) functional groups.

As used herein, the term "heteroaryl group" means that the aryl group contains 1 to 3 hetero atoms selected from the group consisting of N, O, S, P, and Si, and the remainder is carbon. 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 may be substituted or unsubstituted phenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthracenyl group, substituted or unsubstituted phenanthryl group, A substituted 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 m-terphenyl group, a substituted or unsubstituted quinicenyl group , A substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted perylenyl group, a substituted or unsubstituted indenyl group, a substituted or unsubstituted fluorenyl group,

The substituted or unsubstituted C2 to C30 heteroaryl group may be substituted or unsubstituted furanyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted Substituted or unsubstituted oxadiazole groups, substituted or unsubstituted thiadiazole groups, substituted or unsubstituted thiadiazole groups, substituted or unsubstituted thiadiazole groups, substituted or unsubstituted thiadiazole groups, substituted or unsubstituted thiadiazole groups, , A substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted pyrazinyl group, a substituted or unsubstituted thiazinyl group, a substituted or unsubstituted benzofuranyl group, a substituted or unsubstituted pyrazinyl group, Substituted or unsubstituted quinolinyl groups, substituted or unsubstituted isoquinolinyl groups, substituted or unsubstituted benzimidazolyl groups, substituted or unsubstituted indolyl groups, substituted or unsubstituted quinolinyl groups, substituted or unsubstituted isoquinolinyl groups, A substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted quinoxalinyl group, a substituted or unsubstituted naphthyridinyl group, a substituted or unsubstituted benzoxazinyl group, a substituted or unsubstituted benzothiazine group, a substituted or unsubstituted acridine Substituted or unsubstituted dibenzothiophenyl groups, substituted or unsubstituted dibenzothiophenyl groups, substituted or unsubstituted dibenzothiophenyl groups, substituted or unsubstituted dibenzothiophenyl groups, substituted or unsubstituted dibenzothiophenyl groups, substituted or unsubstituted dibenzothiophenyl groups, A substituted or unsubstituted carbazolyl group, or a combination thereof.

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 composition according to one embodiment will be described below.

The composition according to one embodiment comprises at least two types of host and a dopant, wherein the host comprises a first host compound and a second host compound, each of which is represented by the following formulas I and II .

(I) < RTI ID = 0.0 > (II)

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In the above formulas (I) and (II)

R _1a to R _5a each independently represent a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or A combination thereof,

R _1b to R _5b are each independently a substituted or unsubstituted C2 to C30 heteroaryl group containing at least one N except for a substituted or unsubstituted carbazolyl group,

X ₁ and X ₃ are each independently O, Se, S, SO, SO ₂ , PO or CO,

X ₂ and X ₄ are each independently CR _a R _b or SiR _c R _d ,

R _a to R _d each independently represent hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted C2 to C30 heteroaryl group, a substituted or unsubstituted amine group, a substituted or unsubstituted C6 to C30 arylamine group, a substituted or unsubstituted C3 to C30 heteroaryl amine A substituted or unsubstituted C1 to C30 alkoxy group, a substituted or unsubstituted C2 to C30 alkoxycarbonyl group, a substituted or unsubstituted C2 to C30 alkoxycarbonylamino group, a substituted or unsubstituted C7 to C30 aryloxycarbonylamino group , A substituted or unsubstituted C1 to C30 sulfamoylamino group, a substituted or unsubstituted C2 to C30 alkenyl group, a substituted or unsubstituted C2 to C30 alkynyl group, A substituted or unsubstituted C1 to C20 acyl group, a substituted or unsubstituted C1 to C20 acylamino group, a substituted or unsubstituted C1 to C30 acyl group, a substituted or unsubstituted C1 to C20 acyloxy group, a substituted or unsubstituted C1 to C20 acylamino group, A substituted or unsubstituted C1 to C30 alkylthiol group, a substituted or unsubstituted C1 to C30 heterocyclic thiol group, a substituted or unsubstituted C6 to C30 arylthiol group, a substituted or unsubstituted C1 to C30 arylthiol group, A C1 to C30 heteroarylthiol group, a substituted or unsubstituted C1 to C30 ureide group, a halogen group, a halogen-containing group, a cyano group, a hydroxyl group, an amino group, a nitro group, a carboxyl group, a ferrocenyl group or a combination thereof.

The first host compound may be represented by any one of the following general formulas I-A to I-C, depending on the bonding position of the substituent,

The second host compound may be represented by any of the following formulas (II-A) to (II-C) depending on the bonding position of the substituent.

[Chemical Formula I-A] [Chemical Formula I-B] [Chemical Formula I-C]

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[Formula II-A] Formula (II-B) Formula (II-C)

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In the above formulas I-A to II-C, X ₁ to X ₄ , R _1a to R _5a , and R _1b to R _5b are as described above.

The first host compound may be represented by, for example, any one of the following formulas (I-a) to (I-f)

The second host compound may be represented by any one of the following general formulas (II-a) to (II-f).

[Formula I-a] [Formula I-b] [Formula I-c]

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[Formula I-d] [Formula I-e] [Formula I-f]

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[Formula II-a] [Formula II-b] [Formula II-c]

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[Formula II-d] [Formula II-e] [Formula II-f]

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In the above formulas (I-a) to (II-f)

R _1a to R _5a , and R _1b to R _5b are as described above.

Each of R &_lt; _1a > to R &_lt; _5a &_gt; may independently be selected from the functional groups listed in Group 1 below.

[Group 1]

In the group 1,

R, R 'and R ¹⁰¹ to R ¹³² each independently represent hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C1 to C30 silyl group, a substituted or unsubstituted C6 to C30 aryl group, Or a combination thereof,

* Is a connecting point and may be located in any of the elements forming the functional group.

The functional groups listed in the group 1 may be selected from substituted or unsubstituted groups represented by the following formulas A-1 to A-15.

 [A-1] [A-2] [A-3] [A-4]

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[A-7] [A-8] [A-9] [A-10]

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[A-12] [A-13] [A-14] [A-15]

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In the above Formulas A-1 to A-16, * is a connecting point.

R _1b to R _5b may each independently be selected from a substituted or unsubstituted functional group listed in the following group 2.

[Group 2]

In the group 2,

Z is each independently N or CR ^a , at least one of Z is N,

W and Y are each independently N, O, S, SO, SO 2, CR b, CR c R d, SiR e or SiR ^f R ^g,

Wherein each of R ^a to R ^g is independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C3 to C30 cycloalkyl group, a substituted or unsubstituted C3 to C30 heterocycloalkyl group, A substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group,

* Is a connecting point and may be located in any of the elements forming the functional group.

The functional groups listed in the group 2 may be selected from substituted or unsubstituted groups represented by the following formulas B-1 to B-35.

[B-1] [B-2] [B-3] [B-4]

[B-6] [B-7] [B-8] [B-9]

[B-11] [B-12] [B-13] [B-14]

[B-16] [B-17] [B-18] [B-19]

[B-21] [B-22] [B-23] [B-24]

[B-26] [B-27] [B-28] [B-29] [B-30]

[B-31] [B-32] [B-33] [B-34]

In the above Formulas B-1 to B-35, * is a connecting point.

The first host compound and the second host compound may be, for example, the compounds listed in Table 1 and Table 2, wherein the substituent means R _2a when the core moiety is I-a and I-d, a and II-d, R _2b means the case where the core moiety is I-b and I-e, R _3a means the core moiety and R _3b when the core moiety is II-b and II-e, In the case of I-c and I-f, it means R _4a , and when the core moiety is II-c and II-f, it means R _4b , and all substituents not specifically mentioned are all hydrogen.

compound
number core Substituent compound
number core Substituent compound
number core Substituent I-1 I-a A-1 I-41 I-c A-9 I-81 I-f A-1 I-2 I-a A-2 I-42 I-c A-10 I-82 I-f A-2 I-3 I-a A-3 I-43 I-c A-11 I-83 I-f A-3 I-4 I-a A-4 I-44 I-c A-12 I-84 I-f A-4 I-5 I-a A-5 I-45 I-c A-13 I-85 I-f A-5 I-6 I-a A-6 I-46 I-c A-14 I-86 I-f A-6 I-7 I-a A-7 I-47 I-c A-15 I-87 I-f A-7 I-8 I-a A-8 I-48 I-c A-16 I-88 I-f A-8 I-9 I-a A-9 I-49 I-d A-1 I-89 I-f A-9 I-10 I-a A-10 I-50 I-d A-2 I-90 I-f A-10 I-11 I-a A-11 I-51 I-d A-3 I-91 I-f A-11 I-12 I-a A-12 I-52 I-d A-4 I-92 I-f A-12 I-13 I-a A-13 I-53 I-d A-5 I-93 I-f A-13 I-14 I-a A-14 I-54 I-d A-6 I-94 I-f A-14 I-15 I-a A-15 I-55 I-d A-7 I-95 I-f A-15 I-16 I-a A-16 I-56 I-d A-8 I-96 I-f A-16 I-17 I-b A-1 I-57 I-d A-9 I-18 I-b A-2 I-58 I-d A-10 I-19 I-b A-3 I-59 I-d A-11 I-20 I-b A-4 I-60 I-d A-12 I-21 I-b A-5 I-61 I-d A-13 I-22 I-b A-6 I-62 I-d A-14 I-23 I-b A-7 I-63 I-d A-15 I-24 I-b A-8 I-64 I-d A-16 I-25 I-b A-9 I-65 I-e A-1 I-26 I-b A-10 I-66 I-e A-2 I-27 I-b A-11 I-67 I-e A-3 I-28 I-b A-12 I-68 I-e A-4 I-29 I-b A-13 I-69 I-e A-5 I-30 I-b A-14 I-70 I-e A-6 I-31 I-b A-15 I-71 I-e A-7 I-32 I-b A-16 I-72 I-e A-8 I-33 I-c A-1 I-73 I-e A-9 I-34 I-c A-2 I-74 I-e A-10 I-35 I-c A-3 I-75 I-e A-11 I-36 I-c A-4 I-76 I-e A-12 I-37 I-c A-5 I-77 I-e A-13 I-38 I-c A-6 I-78 I-e A-14 I-39 I-c A-7 I-79 I-e A-15 I-40 I-c A-8 I-80 I-e A-16

compound
number core Substituent compound
number core Substituent compound
number core Substituent II-1 II-a B-1 Ⅱ-71 II-c B-1 II-141 II-e B-1 II-2 II-a B-2 II-72 II-c B-2 II-142 II-e B-2 II-3 II-a B-3 II-73 II-c B-3 II-143 II-e B-3 Ⅱ-4 II-a B-4 II-74 II-c B-4 II-144 II-e B-4 II-5 II-a B-5 Ⅱ-75 II-c B-5 II-145 II-e B-5 Ⅱ-6 II-a B-6 II-76 II-c B-6 II-146 II-e B-6 Ⅱ-7 II-a B-7 II-77 II-c B-7 Ⅱ-147 II-e B-7 II-8 II-a B-8 II-78 II-c B-8 Ⅱ-148 II-e B-8 II-9 II-a B-9 II-79 II-c B-9 Ⅱ-149 II-e B-9 II-10 II-a B-10 II-80 II-c B-10 II-150 II-e B-10 II-11 II-a B-11 II-81 II-c B-11 II-151 II-e B-11 Ⅱ-12 II-a B-12 II-82 II-c B-12 II-152 II-e B-12 Ⅱ-13 II-a B-13 II-83 II-c B-13 Ⅱ-153 II-e B-13 II-14 II-a B-14 II-84 II-c B-14 II-154 II-e B-14 Ⅱ-15 II-a B-15 II-85 II-c B-15 Ⅱ-155 II-e B-15 II-16 II-a B-16 II-86 II-c B-16 Ⅱ-156 II-e B-16 II-17 II-a B-17 Ⅱ-87 II-c B-17 II-157 II-e B-17 II-18 II-a B-18 II-88 II-c B-18 II-158 II-e B-18 Ⅱ-19 II-a B-19 II-89 II-c B-19 II-159 II-e B-19 Ⅱ-20 II-a B-20 Ⅱ-90 II-c B-20 Ⅱ-160 II-e B-20 Ⅱ-21 II-a B-21 Ⅱ-91 II-c B-21 II-161 II-e B-21 II-22 II-a B-22 II-92 II-c B-22 II-162 II-e B-22 Ⅱ-23 II-a B-23 II-93 II-c B-23 II-163 II-e B-23 Ⅱ-24 II-a B-24 II-94 II-c B-24 II-164 II-e B-24 Ⅱ-25 II-a B-25 II-95 II-c B-25 II-165 II-e B-25 II-26 II-a B-26 II-96 II-c B-26 II-166 II-e B-26 II-27 II-a B-27 II-97 II-c B-27 II-167 II-e B-27 Ⅱ-28 II-a B-28 II-98 II-c B-28 Ⅱ-168 II-e B-28 Ⅱ-29 II-a B-29 II-99 II-c B-29 II-169 II-e B-29 Ⅱ-30 II-a B-30 II-100 II-c B-30 II-170 II-e B-30 Ⅱ-31 II-a B-31 II-101 II-c B-31 II-171 II-e B-31 Ⅱ-32 II-a B-32 II-102 II-c B-32 II-172 II-e B-32 II-33 II-a B-33 II-103 II-c B-33 II-173 II-e B-33 Ⅱ-34 II-a B-34 II-104 II-c B-34 II-174 II-e B-34 Ⅱ-35 II-a B-35 Ⅱ-105 II-c B-35 II-175 II-e B-35 Ⅱ-36 II-b B-1 II-106 II-d B-1 II-176 II-f B-1 Ⅱ-37 II-b B-2 II-107 II-d B-2 II-177 II-f B-2 II-38 II-b B-3 II-108 II-d B-3 II-178 II-f B-3 Ⅱ-39 II-b B-4 II-109 II-d B-4 II-179 II-f B-4 II-40 II-b B-5 II-110 II-d B-5 Ⅱ-180 II-f B-5 II-41 II-b B-6 II-111 II-d B-6 Ⅱ-181 II-f B-6 II-42 IIb B-7 II-112 II-d B-7 II-182 II-f B-7 Ⅱ-43 II-b B-8 II-113 II-d B-8 II-183 II-f B-8 II-44 II-b B-9 II-114 II-d B-9 II-184 II-f B-9 Ⅱ-45 II-b B-10 II-115 II-d B-10 II-185 II-f B-10 Ⅱ-46 II-b B-11 II-116 II-d B-11 II-186 II-f B-11 Ⅱ-47 II-b B-12 II-117 II-d B-12 II-187 II-f B-12 Ⅱ-48 II-b B-13 II-118 II-d B-13 II-188 II-f B-13 II-49 II-b B-14 II-119 II-d B-14 II-189 II-f B-14 Ⅱ-50 II-b B-15 II-120 II-d B-15 Ⅱ-190 II-f B-15 II-51 II-b B-16 Ⅱ-121 II-d B-16 II-191 II-f B-16 II-52 II-b B-17 II-122 II-d B-17 II-192 II-f B-17 Ⅱ-53 II-b B-18 Ⅱ-123 II-d B-18 II-193 II-f B-18 Ⅱ-54 II-b B-19 II-124 II-d B-19 II-194 II-f B-19 Ⅱ-55 II-b B-20 II-125 II-d B-20 II-195 II-f B-20 II-56 II-b B-21 II-126 II-d B-21 II-196 II-f B-21 Ⅱ-57 II-b B-22 II-127 II-d B-22 II-197 II-f B-22 Ⅱ-58 II-b B-23 Ⅱ-128 II-d B-23 II-198 II-f B-23 Ⅱ-59 II-b B-24 II-129 II-d B-24 II-199 II-f B-24 Ⅱ-60 II-b B-25 II-130 II-d B-25 II-200 II-f B-25 Ⅱ-61 II-b B-26 II-131 II-d B-26 Ⅱ-201 II-f B-26 II-62 II-b B-27 II-132 II-d B-27 II-202 II-f B-27 II-63 II-b B-28 II-133 II-d B-28 Ⅱ-203 II-f B-28 Ⅱ-64 II-b B-29 II-134 II-d B-29 Ⅱ-204 II-f B-29 II-65 II-b B-30 Ⅱ-135 II-d B-30 Ⅱ-205 II-f B-30 Ⅱ-66 II-b B-31 II-136 II-d B-31 Ⅱ-206 II-f B-31 II-67 II-b B-32 Ⅱ-137 II-d B-32 II-207 II-f B-32 Ⅱ-68 II-b B-33 II-138 II-d B-33 II-208 II-f B-33 Ⅱ-69 II-b B-34 II-139 II-d B-34 II-209 II-f B-34 II-70 II-b B-35 II-140 II-d B-35 Ⅱ-210 II-f B-35

The first host compound may be represented, for example, by any of the compounds listed below.

[Formula I-2] [Formula I-4] [Formula I-5] [Formula I-7]

[Formula I-8] [Formula I-10] [Formula I-11] [Formula I-12]

[Formula I-13] [Formula I-14] [Formula I-15] [Formula I-16]

[Formula I-18] [Formula (I-20)] [Formula (I-21)

[Formula I-24] [Formula I-26] [Formula I-27] [Formula I-28]

 [Formula I-29] [Formula I-30] [Formula I-31] [Formula I-32]

[Formula I-34] [Formula I-36] [Formula I-37] [Formula I-39]

[Formula I-40] [Formula I-42] [Formula I-43] [Formula I-44]

 [Formula I-45] [Formula I-46] [Formula I-47] [Formula I-48]

[Formula I-50] [Formula (I-52)] [Formula (I-53)

[Formula I-56] [Formula (I-58)] [Formula (I-61)

[Formula I-63] [Formula I-64] [Formula I-68] [Formula I-69]

[Formula I-71] [Formula (I-72)] [Formula (I-74)

[Formula I-78] [Formula (I-79)] [Formula (I-80)

[Formula I-84] [Formula (I-85)] [Formula (I-87)

[Formula I-90] [Formula (I-93)] [Formula (I-95)

The second host compound may be represented, for example, by any one of the compounds listed below.

[Formula II-13] [Formula II-16] [Formula II-18] [Formula II-23]

[Formula II-28] [Formula (II-51)] (Formula (II-53)

[Formula II-61] [Formula (II-63)] (Formula (II-83)

[Formula II-88] [Formula (II-98)] (Formula (II-118)

[Formula II-123] [Formula (II-128)] [Formula (II-133)

[Formula II-158] [Formula (II-163)] (Formula (II-166)

[Formula II-193]

The first host compound and the second host compound described above can be prepared in various compositions in various combinations. For example, a composition comprising the first host compound and the second host compound.

For example, the composition may be a composition wherein a compound selected from the compounds of the formula (I) shown in Table 1 is used as the first host and a compound selected from the compounds of the formula (I) shown in Table 2 is used as the second host.

 The compounds listed in Table 1 and Table 2 illustrate various first and second host compounds, but are not limited thereto.

As described above, the first host compound is a compound having hole characteristics, and the second host compound is a compound having electronic characteristics, so that the bipolar characteristics can be realized by including them together. Therefore, when the composition is applied to the light emitting layer of an organic optoelectronic device, it is possible to improve the good interfacial characteristics and the transportability of holes and electrons.

The first host compound and the second host compound may be contained in a weight ratio of, for example, 1:10 to 10: 1. When the hole transporting ability of the first host compound and the electron transporting ability of the second host compound are adjusted to be appropriate, the light emitting layer can be formed to improve the efficiency and lifetime by implementing the bipolar characteristics.

The composition may further include at least one host compound in addition to the first host compound and the second host compound.

The composition may further comprise a dopant. The dopant may be a red, green or blue dopant, for example a phosphorescent dopant.

The dopant may be a metal complex that emits light by multiple excitation that is excited by a triplet state or higher, and is a substance that emits light by mixing with the first host compound and the second host compound. May be used. The dopant may be, for example, an inorganic, organic, or organic compound, and may include one or more species.

Examples of the phosphorescent dopant include organic metal compounds including Ir, Pt, Os, Ti, Zr, Hf, Eu, Tb, Tm, Fe, Co, Ni, Ru, Rh and Pd or combinations thereof. The phosphorescent dopant can be, for example, compounds represented by the following formulas (A) to (C), but is not limited thereto.

[Chemical Formula B] [Chemical Formula C]

The composition may be formed by a dry film forming method such as chemical vapor deposition.

Hereinafter, an organic optoelectronic device to which the above-described composition 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.

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 including the above-described composition.

The light emitting layer 130 may include, for example, the above-described composition.

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.

In one embodiment of the present invention, the organic thin film layer 105 may further include an electron transport layer, an electron injection layer, a hole injection layer, and the like, as shown in FIG. 1 or FIG.

The organic light emitting devices 100 and 200 may be formed by forming an anode or a cathode on a substrate and then forming an organic layer by a dry film forming method such as evaporation, sputtering, plasma plating, or ion plating, A negative electrode or a positive electrode.

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

Hereinafter, specific embodiments of the present invention will be described. However, the embodiments described below are only intended to illustrate or explain the present invention, and thus the present invention should not be limited thereto.

Synthesis of organic compounds

Synthesis of intermediate 1-a

[Reaction Scheme 1]

A first step; Synthesis of intermediate product (A)

24.5 g (113.9 mmol) of methyl-2-bromo-benzoate and 6.3 g (5.47 mmol) of tetrakistriphenylphosphine palladium were added to a solution of 23 g (108.5 mmol) of 4-dibenzofuranyl boronic acid, mmol) were dissolved in 500 ml of toluene under a nitrogen atmosphere, 271.2 ml of an aqueous solution containing 79.9 g (542.4 mmol) of potassium carbonate was added, and the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate. The extract was dried with magnesium sulphate, filtered and the filtrate was concentrated under reduced pressure. The product was purified by silica gel column chromatography with n-hexane / dichloromethane (7: 3 by volume) to give 31 g (94.5% yield) of intermediate (A) as a white solid.

LC-Mass (theory: 302.32 g / mol, measurement: M + 1 = 302 g / mol)

A second step; Synthesis of intermediate product (B)

29 g (95.92 mmol) of the intermediate (A) was placed in a flask, and dissolved in 400 ml of anhydrous tetrahydrofuran (THF) under a nitrogen atmosphere. The mixture was cooled to 0 캜 and stirred. 95.9 mL (in diethyl ether, 287.8 mmol) of 3M methylmagnesiumbromide was slowly added thereto, followed by stirring at room temperature under a nitrogen atmosphere for 5 hours. After completion of the reaction, the solution was concentrated under reduced pressure to remove the solvent, followed by extraction with distilled water and dichloromethane. The extract was dried with magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure to obtain the desired intermediate (B) Lt; / RTI >

A third step; Synthesis of intermediate product (C)

Intermediate (B) was dissolved in 250 ml of dichloromethane, cooled to 0 캜 and stirred. Borontrifluoride and diethyl ether complex (12.84 g, 47.5 mmol) dissolved in 20 mL of dichloromethane were slowly added thereto, followed by stirring at room temperature for 5 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate. The extract was dried with magnesium sulphate, filtered and the filtrate was concentrated under reduced pressure. The product was purified by silica gel column chromatography with n-hexane to obtain 22 g (yield: 71.9%) of intermediate compound (C) as a white solid.

LC-Mass (theory: 284.35 g / mol, measurement: M + 1 = 284 g / mol)

Step 4; Synthesis of intermediate product 1-a

70 g (246.18 mmol) of Intermediate (C) was added to a 2-necked round-bottomed flask heated and dried under vacuum, and 500 mL of anhydrous tetrahydrofuran was added to dissolve it. 118 mL (in Hexane, 295.41 mmol) of 2.5M n-butyllithium was slowly added thereto, followed by stirring at room temperature under a nitrogen atmosphere for 6 hours. After the reaction solution was cooled to -78 ° C, 68.17 mL (295.41 mmol) of triisopropyl borate was slowly added thereto, followed by stirring at room temperature for 12 hours. After completion of the reaction with 3N HCl aqueous solution, the reaction mixture was extracted with ethyl acetate, and the extract was dried with magnesium sulphate, filtered and the filtrate was concentrated under reduced pressure. The product was purified by a silica gel filter to obtain 62.5 g (yield 77%) of Intermediate 1-a of interest.

LC-Mass (theory: 328.17 g / mol, measurement: M + 1 = 328 g / mol)

Synthesis of Intermediate 1-b

[Reaction Scheme 2]

A first step; Synthesis of intermediate product (D)

30 g (141.5 mmol) of (4-dibenzofuranyl) boronic acid, methyl-2-bromo-5-chlorobenzoate 37.1 g (148.6 mmol) of tetrakistriphenylphosphine palladium and 8.2 g (7.1 mmol) of tetrakistriphenylphosphine palladium were placed in a flask and dissolved in 550 ml of toluene under a nitrogen atmosphere. 353.8 ml of an aqueous solution obtained by dissolving 104.2 g (707.51 mmol) of potassium carbonate And the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate. The extract was dried with magnesium sulphate, filtered and the filtrate was concentrated under reduced pressure. The product was purified by silica gel column chromatography with n-hexane / dichloromethane (7: 3 by volume) to give 38.2 g (80% yield) of intermediate (D) as a white solid.

LC-Mass (theory: 336.06 g / mol, measured: M + 1 = 336 g / mol)

A second step; Synthesis of intermediate product (E)

38.18 g (113.37 mmol) of Intermediate (D) was placed in a flask and dissolved in 500 ml of anhydrous ether under a nitrogen atmosphere, followed by cooling to 0 ° C and stirring. Thereto was slowly added 110 mL of 3M methylmagnesium bromide (in diethyl ether, 340.1 mmol) and the mixture was stirred at room temperature under a nitrogen atmosphere for 5 hours. After completion of the reaction, the solution was concentrated under reduced pressure to remove the solvent, followed by extraction with distilled water and dichloromethane. The extract was dried with anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain the desired intermediate (E) Respectively.

A third step; Synthesis of intermediate product (F)

Intermediate (E) was dissolved in 250 ml of dichloromethane, followed by cooling to 0 ° C and stirring. Borontrifluoride and diethyl ether complex (15.18 g, 56.7 mmol) dissolved in 20 mL of dichloromethane were slowly added thereto, followed by stirring at room temperature for 5 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate. The extract was dried with magnesium sulphate, filtered and the filtrate was concentrated under reduced pressure. The product was purified by silica gel column chromatography with n-hexane to obtain 29 g (yield 80%) of intermediate compound (F) as a white solid.

GC-Mass (theory: 318.8 g / mol, measured: M + 1 = 318 g / mol)

Step 4; Synthesis of intermediate product 1-b

29 g (90.97 mmol) of Intermediate (F) was added to a 2-necked round-bottomed flask heated and dried under vacuum, 300 mL of anhydrous tetrahydrofuran was added to dissolve it, and the mixture was cooled to -78 ° C and stirred. 68.2 mL (in hexane, 109.16 mmol) of 1.6M n-butyllithium was slowly added thereto, followed by stirring at room temperature under a nitrogen atmosphere for 6 hours. After the reaction solution was cooled to -78 ° C, 7.61 mL (109.16 mmol) of trimethyl borate was slowly added thereto, followed by stirring at room temperature for 12 hours. After completion of the reaction with 3N HCl aqueous solution, the reaction mixture was extracted with ethyl acetate, and the extract was dried with magnesium sulphate, filtered and the filtrate was concentrated under reduced pressure. The product was purified by a silica gel filter to obtain 23 g (yield 77%) of intermediate compound 1-b as a target compound.

Synthesis of Intermediate 1-c

[Reaction Scheme 3]

A first step; Synthesis of intermediate product (G)

30 g (141.5 mmol) of (4-dibenzofuranyl) boronic acid, methyl-2-bromo-5-chlorobenzoate 37.1 g (148.6 mmol) of tetrakistriphenylphosphine palladium and 8.2 g (7.1 mmol) of tetrakistriphenylphosphine palladium were placed in a flask and dissolved in 550 ml of toluene under a nitrogen atmosphere. 353.8 ml of an aqueous solution obtained by dissolving 104.2 g (707.51 mmol) of potassium carbonate And the mixture was refluxed for 12 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate. The extract was dried with magnesium sulphate, filtered and the filtrate was concentrated under reduced pressure. The product was purified by silica gel column chromatography with n-hexane / dichloromethane (7: 3 by volume) to give 38.2 g (80% yield) of intermediate (G) as a white solid.

LC-Mass (theory: 336.06 g / mol, measured: M + 1 = 336 g / mol)

A second step; Synthesis of intermediate product (H)

38.18 g (113.37 mmol) of Intermediate (G) was placed in a flask and dissolved in 500 ml of anhydrous ether under a nitrogen atmosphere, followed by cooling to 0 ° C and stirring. Thereto was slowly added 110 mL of 3M methylmagnesium bromide (in diethyl ether, 340.1 mmol) and the mixture was stirred at room temperature under a nitrogen atmosphere for 5 hours. After completion of the reaction, the solution was concentrated under reduced pressure to remove the solvent, followed by extraction with distilled water and dichloromethane. The extract was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain the desired intermediate (H) Respectively.

A third step; Synthesis of intermediate product (I)

Intermediate (H) was dissolved in 250 ml of dichloromethane, cooled to 0 캜 and stirred. Borontrifluoride and diethyl ether complex (15.18 g, 56.7 mmol) dissolved in 20 mL of dichloromethane were slowly added thereto, followed by stirring at room temperature for 5 hours. After completion of the reaction, the reaction mixture was extracted with ethyl acetate. The extract was dried with magnesium sulphate, filtered and the filtrate was concentrated under reduced pressure. The product was purified by silica gel column chromatography with n-hexane to obtain 29 g (yield 80%) of intermediate compound (I) as a white solid.

GC-Mass (theory: 318.8 g / mol, measured: M + 1 = 318 g / mol)

Step 4; Synthesis of intermediate product 1-c

29 g (90.97 mmol) of Intermediate (I) was added to a 2-necked round-bottomed flask heated and dried under vacuum, 300 mL of anhydrous tetrahydrofuran was added to dissolve it, and the mixture was cooled to -78 ° C and stirred. 68.2 mL (in hexane, 109.16 mmol) of 1.6M n-butyllithium was slowly added thereto, followed by stirring at room temperature under a nitrogen atmosphere for 6 hours. After the reaction solution was cooled to -78 ° C, 7.61 mL (109.16 mmol) of trimethyl borate was slowly added thereto, followed by stirring at room temperature for 12 hours. After completion of the reaction with 3N HCl aqueous solution, the reaction mixture was extracted with ethyl acetate, and the extract was dried with magnesium sulphate, filtered and the filtrate was concentrated under reduced pressure. The product was purified by a silica gel filter to obtain 23 g (yield 77%) of Intermediate 1-c as a target compound.

Synthesis of intermediate 1-d

The synthesis starting material is (4-dibenzothienyl) boronic acid, and intermediate 1-d was synthesized as in Intermediate 1-a via the same step path as in Scheme 4 below.

[Reaction Scheme 4]

Synthesis of Intermediate 1-e

Synthesis starting material is 4-dibenzothienyl) boronic acid, and intermediates 1-e of the title are synthesized as in Intermediate 1-b via the following Scheme 5:

[Reaction Scheme 5]

Synthesis of Intermediate 1-f

The synthesis starting material is (4-dibenzothienyl) boronic acid, and intermediate 1-f was synthesized as in Intermediate 1-c via the following step sequence as shown in Scheme 6 below.

[Reaction Scheme 6]

Synthesis of first host compound

Example  1: Synthesis of first host formula I-4

[Reaction Scheme 7]

(0.55 mmmol) of tetrakis- (triphenylphosphine) palladium (0), 11.49 g (83.11 mmol) of potassium carbonate, 8.57 g (27.7 mmol) of Compound A- Was suspended in toluene (100 ml) and distilled water (40 ml), and the mixture was refluxed for 12 hours. Extraction is carried out with dichloromethane and distilled water, and the organic layer is subjected to silica gel filtration. The organic solution was removed, and the residue was subjected to silica gel column chromatography with hexane: dichloromethane = 7: 3 (v / v), and the resulting solid was recrystallized from dichloromethane and normal hexane to obtain 12 g (yield: 85%) of the compound of formula .

Example  2 to 14: Preparation of compound

The compounds were synthesized in the same manner as in Example 1 except that the compounds listed in Table 3 were used instead of the intermediate I-a and the compound A-4 in Example 1, respectively.

Example Starting material 1 Starting material 2 product yield(%)
LC-Mass (M + H ^& lt ^{; +} & gt ^; ) 2

I-a

Ia

I-7 82%
511.20 3

Ia

I-13 84%
467.15 4

Ia

I-15 79%
526.22 5

Id

I-52 84%
529.19 6

Id

I-63 81%
542.19 7

Ic

I-36 87%
513.23 8

Ic

I-47 78%
526.21 9

If

I-84 84%
529.20 10

If

I-95 82%
542.19 11

Ib

I-20 85%
513.22 12

Ib

I-31 80%
526.21 13

Ie

I-68 83%
529.20 14

Ie

I-79 82%
542.19

Synthesis of second host compound

Example  15: Synthesis of the 2nd host formula II-128

[Reaction Scheme 8]

0.61 g (0.53 mmmol) of tetrakis- (triphenylphosphine) palladium (0), 10.95 g (79.23 mmol) of potassium carbonate, 10.3 g (26.4 mmol) of compound B- Was suspended in toluene (100 ml) and distilled water (40 ml), and the mixture was refluxed for 12 hours. Extraction is carried out with dichloromethane and distilled water, and the organic layer is subjected to silica gel filtration. The organic solution was removed, and the residue was subjected to silica gel column chromatography with hexane: dichloromethane = 7: 3 (v / v), and the resulting solid was recrystallized from dichloromethane and normal hexane to obtain 14 g (yield: 87%) of a compound represented by the formula II- .

Example  16 to 30: Preparation of compound

The compounds were synthesized in the same manner as in Example 15 except that the compounds listed in Table 4 were used instead of the intermediate I-d of Example 15 and the compound B-23.

Example Starting material 1 Starting material 2 product yield(%)
LC-Mass (M + H ^& lt ^{; +} & gt ^; ) 16

I-a

Ia

II-16 82%
515.21 17

Ia

II-18 80%
516.20 18

Ia

Ⅱ-23 78%
592.23 19

Id

Ⅱ-121 85%
531.19 20

Id

II-133 79%
608.21 21

Ic

II-86 88%
515.21 22

Ic

II-88 89%
516.20 23

Ic

II-98 82%
592.23 24

If

II-193 88%
532.18 25

Ib

II-51 87%
515.21 26

Ib

Ⅱ-53 85%
516.20 27

Ib

Ⅱ-61 77%
591.24 28

Ib

II-63 80%
592.23 29

Ie

Ⅱ-156 84%
531.19 30

Ie

II-163 80%
608.21

Fabrication of organic light emitting device

Example  31

As the anode, ITO was used in a thickness of 1000 Å, and as a cathode, aluminum (Al) was used in a thickness of 1000 Å. Specifically, an explanation will be given of a method of manufacturing an organic light emitting device. An ITO glass substrate having a sheet resistance of 15 Ω / cm ² is cut into a size of 50 mm × 50 mm × 0.7 mm, and is cut in acetone, isopropyl alcohol and pure water After ultrasonic cleaning for 15 minutes each, UV ozone cleaning was performed for 30 minutes.

The following HTM was deposited on the substrate at a vacuum degree of 650 × 10 ^-7 Pa and a deposition rate of 0.1 to 0.3 nm / s to form a 1200 Å hole transport layer.

[HTM]

Subsequently, the compound I-4 obtained in Example 1 and the compound II-128 obtained in Example 15 were vapor-deposited together at a weight ratio of 1: 1 under the same vacuum deposition conditions and used as a host. PhGD, a phosphorescent green dopant, And a 300 Å thick light emitting layer was formed by vapor deposition. At this time, the deposition rate of the phosphorescent dopant was controlled so that the phosphorescent dopant content was 10% by weight when the total amount of the light emitting layer was 100% by weight.

[PhGD]

Bis (2-methyl-8-quinolinolate) -4- (phenylphenolato) aluminum (BAlq) was deposited on the light emitting layer using the same vacuum deposition conditions to form a hole blocking layer having a thickness of 50 Å. Subsequently, Alq3 was deposited under the same vacuum deposition conditions to form an electron transporting layer having a thickness of 250 ANGSTROM. LiF and Al were sequentially deposited on the electron transport layer as cathodes to fabricate an organic photoelectric device.

The structure of the organic photoelectric device was ITO / HTM (120 nm) / EML (Compound I-4 (45 wt%) + Compound II-128 (45 wt%) + PhGD (10 wt% 5 nm) / Alq3 (25 nm) / LiF (1 nm) / Al (100 nm).

Example  32

Example 31 was repeated except that Compound I-20 and Compound II-128 were deposited in a ratio of 1: 1 instead of Compound I-4 and Compound II-128 in Example 31 in a 1: 1 weight ratio. An organic light emitting device was prepared in the same manner.

Example  33

Except that Compound I-31 and Compound II-128 were deposited in a ratio of 1: 1 instead of Compound I-4 and Compound II-128 in Example 31 in a 1: 1 weight ratio. An organic light emitting device was prepared in the same manner.

Example  34

Example 31 was repeated except that Compound I-79 and Compound II-128 were deposited in a ratio of 1: 1 instead of Compound I-4 and Compound II-128 in Example 31 in a 1: 1 weight ratio. An organic light emitting device was prepared in the same manner.

Example  35

Example 34 was repeated except that Compound I-79 and Compound II-128 were deposited in a ratio of 1: 4 instead of Compound I-79 and Compound II-128 in Example 34 in a 1: 1 weight ratio. An organic light emitting device was prepared in the same manner.

Example  36

Example 31 was repeated except that Compound I-4 and Compound II-63 were deposited in a ratio of 1: 1 instead of depositing Compound I-4 and Compound II-128 in Example 31 at a weight ratio of 1: 1. An organic light emitting device was prepared in the same manner.

Example  37

Example 31 was repeated except that Compound I-20 and Compound II-63 were deposited in a ratio of 1: 1 instead of depositing Compound I-4 and Compound II-128 in Example 31 at a weight ratio of 1: 1. An organic light emitting device was prepared in the same manner.

Example  38

Example 31 was repeated except that Compound I-31 and Compound II-63 were deposited in a ratio of 1: 1 instead of Compound I-4 and Compound II-128 in Example 31 in a 1: 1 weight ratio. An organic light emitting device was prepared in the same manner.

Example  39

Example 31 was repeated except that Compound I-79 and Compound II-63 were deposited in a ratio of 1: 1 instead of Compound I-4 and Compound II-128 in Example 31 in a 1: 1 weight ratio. An organic light emitting device was prepared in the same manner.

Comparative Example  One

Except that Compound I-4 was deposited on a host alone instead of Compound I-4 and Compound II-128 in Example 31 in a weight ratio of 1: 1. .

Comparative Example  2

Except that Compound II-128 was deposited as a host alone instead of Compound I-4 and Compound II-128 in Example 31 in a 1: 1 weight ratio. .

Comparative Example  3

Example 20 was repeated except that Compound I-20 was deposited on a host alone instead of Compound I-20 and Compound II-128 in Example 32 in a 1: 1 weight ratio. .

Comparative Example  4

Except that Compound I-31 was deposited by a host alone instead of Compound I-31 and Compound II-128 in Example 33 in a 1: 1 weight ratio. .

Comparative Example  5

Except that Compound I-79 was deposited by a host alone instead of Compound I-79 and Compound II-128 in Example 34 in a 1: 1 weight ratio. .

Comparative Example  6

Except that the compound I-4 and the compound II-63 were deposited in a weight ratio of 1: 1 in Example 36 instead of the compound II-63 in the host alone. .

evaluation

The current density change, the luminance change, and the light emitting efficiency of the organic light emitting devices according to Examples 31 to 39 and Comparative Examples 1 to 6 were measured according to the voltage.

The concrete measurement method is as follows, and the results are shown in Table 5.

(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) Life measurement

The time at which the luminance (cd / m ² ) was kept at 5000 cd / m ² and the current efficiency (cd / A) decreased to 95% was measured and the results were obtained.

Compound used in the light emitting layer The driving voltage (V) color
(EL color) efficiency
(cd / A) 95% lifetime (h)
@ 5000 cd / ㎡ Example 31 I-4 + II-128 (1: 1) 5.13 Green 28.6 200 Example 32 I-20 + II-128 (1: 1) 4.77 Green 27.8 170 Example 33 I-31 + II-128 (1: 1) 4.42 Green 37.5 230 Example 34 I-79 + II-128 (1: 1) 4.38 Green 38.1 260 Example 35 I-79 + II-128 (1: 4) 4.43 Green 29.4 180 Example 36 I-4 + II-63 (1: 1) 5.47 Green 28.3 150 Example 37 I-20 + II-63 (1: 1) 5.18 Green 27.9 100 Example 38 I-31 + II-63 (1: 1) 4.61 Green 33.2 180 Example 39 I-79 + II-63 (1: 1) 4.80 Green 32.5 190 Comparative Example 1 I-4 8.49 Green 21.4 - Comparative Example 2 Ⅱ-128 4.32 Green 23.5 160 Comparative Example 3 I-20 8.08 Green 21.3 - Comparative Example 4 I-31 8.24 Green 19.9 20 Comparative Example 5 I-79 7.68 Green 22.3 25 Comparative Example 6 II-63 4.79 Green 21.2 90

According to Table 5, the organic light emitting devices according to Examples 31 to 39 have significantly improved luminous efficiency and / or life span as compared with the organic light emitting devices according to Comparative Examples 1 to 6.

Specifically, the organic light emitting device according to Example 34 has improved efficiency and life span as compared with Comparative Examples 2 and 5, which are comparative examples, respectively. This shows that the bipolar characteristics of the hole transporting host and the electron transporting host improve the efficiency and lifetime.

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 (14)

A composition comprising a first host compound represented by the formula (I) and a second host compound represented by the formula (II):
(I) < RTI ID = 0.0 > (II)

,

In the above formulas (I) and (II)
R _1a to R _5a each independently represent a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or A combination thereof,
X ₁ and X ₃ are each independently O or S,
X ₂ and X ₄ are CR _a R _b ,
R _a and R _b are each independently hydrogen, deuterium, or a substituted or unsubstituted C1 to C30 alkyl group,
R _1b to R _5b each independently represent a group selected from a substituted or unsubstituted functional group listed in the following group 2,
[Group 2]

In the group 2,
Z is each independently N or CR ^a , at least one of Z is N,
W and Y are each independently N, O, S, CR ^b , or CR ^c R ^d ,
R ^a to R ^d each independently represent hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group,
* Is a connection point and may be located at any one of the elements forming the functional group,
Means that at least one hydrogen in the substituent or the compound is substituted with deuterium, a C1 to C30 alkyl group, a C6 to C30 aryl group, or a C2 to C30 heteroaryl group. The method of claim 1,
The first host compound is represented by any one of the following I-A to I-C,
Wherein the second host compound is represented by any one of the following II-A to II-C:
[Chemical Formula I-A] [Chemical Formula I-B] [Chemical Formula I-C]

,

,

[Formula II-A] Formula (II-B) Formula (II-C)

,

,

In the above formulas (I-A) to (II-C)
R _1a to R _5a each independently represent a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or A combination thereof,
X ₁ and X ₃ are each independently O or S,
X ₂ and X ₄ are CR _a R _b ,
R _a and R _b are each independently hydrogen, deuterium, or a substituted or unsubstituted C1 to C30 alkyl group,
R _1b to R _5b each independently represent a group selected from a substituted or unsubstituted functional group listed in the following group 2,
[Group 2]

In the group 2,
Z is each independently N or CR ^a , at least one of Z is N,
W and Y are each independently N, O, S, CR ^b , or CR ^c R ^d ,
R ^a to R ^d each independently represent hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group,
* Is a connection point and may be located at any one of the elements forming the functional group,
Means that at least one hydrogen in the substituent or the compound is substituted with deuterium, a C1 to C30 alkyl group, a C6 to C30 aryl group, or a C2 to C30 heteroaryl group. The method of claim 1,
Wherein the first host compound is represented by any one of the following formulas (I-a) to (I-f)
Wherein the second host compound is represented by any one of the following formulas II-a to II-f:
[Formula I-a] [Formula I-b] [Formula I-c]

,

,

,
[Formula I-d] [Formula I-e] [Formula I-f]

,

,

[Formula II-a] [Formula II-b] [Formula II-c]

,

,

,
[Formula II-d] [Formula II-e] [Formula II-f]

,

,

In the above formulas (I-a) to (II-f)
R _1a to R _5a each independently represent a substituted or unsubstituted C6 to C30 aryl group, a substituted or unsubstituted carbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or A combination thereof,
R _1b to R _5b each independently represent a group selected from a substituted or unsubstituted functional group listed in the following group 2,
[Group 2]

In the group 2,
Z is each independently N or CR ^a , at least one of Z is N,
W and Y are each independently N, O, S, CR ^b , or CR ^c R ^d ,
R ^a to R ^d each independently represent hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group, or a substituted or unsubstituted C2 to C30 heteroaryl group,
* Is a connection point and may be located at any one of the elements forming the functional group,
Means that at least one hydrogen in the substituent or the compound is substituted with deuterium, a C1 to C30 alkyl group, a C6 to C30 aryl group, or a C2 to C30 heteroaryl group. The method of claim 1,
_Wherein each of R &_lt; _1a > to R &_lt; _5a &_gt; is independently selected from the functional groups listed in the following Group 1:
[Group 1]

In the group 1,
R, R ', and R ¹⁰¹ to R ¹³² are each independently hydrogen, deuterium, a substituted or unsubstituted C1 to C30 alkyl group, a substituted or unsubstituted C6 to C30 aryl group,
* Is a connection point and may be located at any one of the elements forming the functional group,
Means that at least one hydrogen in the substituent or the compound is substituted with deuterium, a C1 to C30 alkyl group, a C6 to C30 aryl group, or a C2 to C30 heteroaryl group. 5. The method of claim 4,
Wherein the functional groups listed in group 1 are selected from substituted or unsubstituted groups represented by the following formulas A-1 to A-15:
[A-1] [A-2] [A-3] [A-4]

,

,

,

,

,

,
[A-7] [A-8] [A-9] [A-10]

,

,

,

,

,
[A-12] [A-13] [A-14] [A-15]

,

,

,

In the above Formulas A-1 to A-16, * is a connecting point,
Means that at least one hydrogen in the substituent or the compound is substituted with deuterium, a C1 to C30 alkyl group, a C6 to C30 aryl group, or a C2 to C30 heteroaryl group. delete The method of claim 1,
Wherein the functional groups listed in the group 2 are selected from substituted or unsubstituted groups represented by the following formulas B-1 to B-35:
[B-1] [B-2] [B-3] [B-4]

[B-6] [B-7] [B-8] [B-9]

[B-11] [B-12] [B-13] [B-14]

[B-16] [B-17] [B-18] [B-19]

[B-21] [B-22] [B-23] [B-24]

[B-26] [B-27] [B-28] [B-29] [B-30]

[B-31] [B-32] [B-33] [B-34]

In the above Formulas B-1 to B-35, * is a connecting point,
Means that at least one hydrogen in the substituent or the compound is substituted with deuterium, a C1 to C30 alkyl group, a C6 to C30 aryl group, or a C2 to C30 heteroaryl group. The method of claim 1,
Wherein said first host compound is represented by any one of the compounds listed below:
[Formula I-2] [Formula I-4] [Formula I-5] [Formula I-7]

[Formula I-8] [Formula I-10] [Formula I-11] [Formula I-12]

[Formula I-13] [Formula I-14] [Formula I-15] [Formula I-16]

[Formula I-18] [Formula (I-20)] [Formula (I-21)

[Formula I-24] [Formula I-26] [Formula I-27] [Formula I-28]

[Formula I-29] [Formula I-30] [Formula I-31] [Formula I-32]

[Formula I-34] [Formula I-36] [Formula I-37] [Formula I-39]

[Formula I-40] [Formula I-42] [Formula I-43] [Formula I-44]

[Formula I-45] [Formula I-46] [Formula I-47] [Formula I-48]

[Formula I-50] [Formula (I-52)] [Formula (I-53)

[Formula I-56] [Formula (I-58)] [Formula (I-61)

[Formula I-63] [Formula I-64] [Formula I-68] [Formula I-69]

[Formula I-71] [Formula (I-72)] [Formula (I-74)

[Formula I-78] [Formula (I-79)] [Formula (I-80)

[Formula I-84] [Formula (I-85)] [Formula (I-87)

[Formula I-90] [Formula (I-93)] [Formula (I-95)

. The method of claim 1,
Wherein the second host compound is represented by any one of the compounds listed below:
[Formula II-13] [Formula II-16] [Formula II-18] [Formula II-23]

[Formula II-28] [Formula (II-51)] (Formula (II-53)

[Formula II-61] [Formula (II-63)] (Formula (II-83)

[Formula II-88] [Formula (II-98)] (Formula (II-118)

[Formula II-123] [Formula (II-128)] [Formula (II-133)

[Formula II-158] [Formula (II-163)] (Formula (II-166)

[Formula II-193]

. The method of claim 1,
Wherein the first host compound and the second host compound are contained in a weight ratio of 1:10 to 10: 1. The method of claim 1,
A composition further comprising a phosphorescent dopant. The positive and negative electrodes facing each other,
And at least one organic layer positioned between the anode and the cathode,
Wherein the organic layer comprises the composition according to any one of claims 1 to 5 and 7 to 11. The method of claim 12,
Wherein the organic layer includes a light emitting layer,
Wherein the light emitting layer comprises the composition. 13. A display device comprising the organic opto-electronic device according to claim 12.

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