US-12628551-B2 - Organic light-emitting device

US12628551B2US 12628551 B2US12628551 B2US 12628551B2US-12628551-B2

Abstract

Provided is an organic light-emitting device including: a first electrode; a second electrode provided to face the first electrode; and a first organic material layer and a second organic material layer provided between the first electrode and the second electrode, in which the first organic material layer includes a compound of Formula 1: wherein L1 to L3 are each independently a direct bond or a substituted or unsubstituted arylene group; and Ar1 to Ar3 are each independently a hydrogen, deuterium, or a substituted or unsubstituted aryl or heterocyclic group; and the second organic material layer includes a compound represented by of Formula 2: wherein L4 is a direct bond, or a substituted or unsubstituted arylene or divalent heterocyclic group; and Ar4 is a substituted or unsubstituted aryl, phosphine oxide or heterocyclic group.

Inventors

Jae Seung Ha
Dong Uk HEO
Min Woo Lee
Sung Jae Lee

Assignees

LG CHEM, LTD.

Dates

Publication Date: 20260512
Application Date: 20190222
Priority Date: 20180223

Claims (18)

1 . An organic light emitting device comprising: a positive electrode; a negative electrode provided to face the positive electrode; a light emitting layer provided between the positive electrode and the negative electrode; a hole injection layer and a hole transport layer successively provided between the positive electrode and the light emitting layer; a first organic material layer provided between the hole transport layer and the light emitting layer; an electron transport layer provided between the negative electrode and the light emitting layer; and a second organic material layer provided between the light emitting layer and the electron transport layer, wherein the first organic material layer comprises a compound of the following Formula 1, and the second organic material layer comprises a compound of the following Formula 2: wherein in Formula 1: L1 is a direct bond; L2 and L3 are each independently a direct bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted terphenylene group; a) Ar1 is deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group that is a dibenzofuran or a dibenzothiophene, and Ar2 is a substituted or unsubstituted heterocyclic group that is a dibenzothiophene; or b) Ar1 is a substituted or unsubstituted heterocyclic group that is a dibenzofuran or a dibenzothiophene, and Ar2 is deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group that is a dibenzothiophene; wherein when any of Ar1 and Ar2 of Formula 1 is a substituted or unsubstituted aryl group, the aryl group is a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a fluorene group, a naphthyl group, or a triphenylene group; Ar3 is a substituted or unsubstituted aryl group; R1 and R2 are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted haloalkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; a and b are each independently an integer from 0 to 4; when a and b are each independently 2 or more, the substituents in the parentheses are the same as or different from each other; wherein in Formula 2: L4 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group; Ar4 is a phenyl group substituted with —CN, a naphthylene group, or trifluoromethoxy group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted fluorene group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; a substituted or unsubstituted benzocarbazole group; a triazine substituted with at least one of a biphenyl, phenyl-substituted naphthylene, dibenzofuran, dibenzothiophene, pyridine, terphenyl group, phenalene, fluorene, phenylpyridine, or dibenzofuran-substituted phenyl; a pyrimidine substituted with at least one of a biphenyl, phenyl-substituted naphthylene, dibenzofuran, dibenzothiophene, pyridine, terphenylene, phenalene, fluorene, or dibenzofuran-substituted phenyl; a quinazoline substituted with phenyl, biphenyl, or naphthyl; an isoquinoline substituted with phenyl; a 1,10-phenanthroline group; a pyridazine substituted with phenyl or naphthyl; a benzo[4,5] imidazo[1,2-f] phenanthridine group; a phenyl-substituted 1,3,4-oxadiazole; a phenyl-substituted 1,3,4-thiadiazole; a fluoranthene group; a dihydrophenoxazine group; or a dihydrophenothiazine group; R3 is hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted haloalkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; c is an integer from 0 to 3; d is 1; m is an integer from 1 to 4; and when c and m are each independently 2 or more, the substituents in the parentheses are the same as or different from each other, with the proviso that the compound of Formula 2 in the second organic material layer is not the following compound:
2 . The organic light emitting device of claim 1 , wherein when Ar3 of Formula 1 is a substituted or unsubstituted aryl group, the aryl group is a phenyl group, a biphenyl group, a terphenyl group, a quaterphenyl group, a fluorene group, a naphthyl group, a phenanthrene group, or a triphenylene group.
3 . The organic light emitting device of claim 1 , wherein Formula 2 is any one of the following Formulae 2-1 to 2-3: wherein in Formulae 2-1 to 2-3, R3, L4, Ar4, c, and d are the same as the definitions in Formula 2.
4 . The organic light emitting device of claim 1 , wherein L4 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group comprising N.
5 . The organic light emitting device of claim 1 , wherein the compound of Formula 2 is selected from among the following compounds:
6 . The organic light emitting device of claim 1 , wherein the first organic material layer is composed of one to three layers.
7 . The organic light emitting device of claim 6 , wherein: the first organic material layer comprises a hole adjusting layer; the hole adjusting layer comprises the compound of Formula 1; and when the hole adjusting layer is composed of two or more layers, the respective layers each independently include the compound of Formula 1 identically or differently.
8 . The organic light emitting device of claim 1 , wherein: the second organic material layer comprises an electron adjusting layer; and the electron adjusting layer comprises the compound of Formula 2.
9 . The organic light emitting device of claim 1 , wherein the compound of Formula 1 is selected from among the following compounds:
10 . An organic light emitting device comprising: a positive electrode: a negative electrode provided to face the positive electrode; a light emitting layer provided between the positive electrode and the negative electrode; a hole injection layer and a hole transport layer successively provided between the positive electrode and the light emitting layer; a first organic material layer provided between the hole transport layer and the light emitting layer; an electron transport layer provided between the negative electrode and the light emitting layer; and a second organic material layer provided between the light emitting layer and the electron transport layer, wherein the second organic material layer comprises a compound of the following Formula 2: wherein in Formula 2: L4 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group; Ar4 is a phenyl group substituted with —CN, a naphthylene group, or trifluoromethoxy group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted fluorene group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; a substituted or unsubstituted benzocarbazole group; a triazine substituted with at least one of a biphenyl, phenyl-substituted naphthylene, dibenzofuran, dibenzothiophene, pyridine, terphenyl group, phenalene, fluorene, phenylpyridine, or dibenzofuran-substituted phenyl; a pyrimidine substituted with at least one of a biphenyl, phenyl-substituted naphthylene, dibenzofuran, dibenzothiophene, pyridine, terphenylene, phenalene, fluorene, or dibenzofuran-substituted phenyl; a quinazoline substituted with phenyl, biphenyl, or naphthyl: an isoquinoline substituted with phenyl: a 1,10-phenanthroline group; a pyridazine substituted with phenyl or naphthyl: a benzo[4,5] imidazo[1,2-f] phenanthridine group; a phenyl-substituted 1,3,4-oxadiazole; a phenyl-substituted 1,3,4-thiadiazole; a fluoranthene group; a dihydrophenoxazine group; or a dihydrophenothiazine group; R3 is hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted haloalkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; c is an integer from 0 to 3; d is 1; m is an integer from 1 to 4; and when c and m are each independently 2 or more, the substituents in the parentheses are the same as or different from each other, with the proviso that the compound of Formula 2 in the second organic material layer is not the following compound: and wherein the first organic material layer comprises a compound selected from among the following compounds:
11 . The organic light emitting device of claim 10 , wherein the compound of Formula 2 is selected from among the following compounds:
12 . An organic light emitting device comprising: a positive electrode; a negative electrode provided to face the positive electrode; a light emitting layer provided between the positive electrode and the negative electrode; a hole injection layer and a hole transport layer successively provided between the positive electrode and the light emitting layer; a first organic material layer provided between the hole transport layer and the light emitting layer; an electron transport layer provided between the negative electrode and the light emitting layer; and a second organic material layer provided between the light emitting layer and the electron transport layer, the second organic material layer comprises a compound of the following Formula 2: wherein in Formula 2: L4 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group; Ar4 is a phenyl group substituted with —CN, a naphthylene group, or trifluoromethoxy group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted terphenyl group; a substituted or unsubstituted fluorene group; a substituted or unsubstituted phenanthrene group; a substituted or unsubstituted triphenylene group; a substituted or unsubstituted dibenzofuran group; a substituted or unsubstituted dibenzothiophene group; a substituted or unsubstituted benzocarbazole group; a triazine substituted with at least one of a biphenyl, phenyl-substituted naphthylene, dibenzofuran, dibenzothiophene, pyridine, terphenyl group, phenalene, fluorene, phenylpyridine, or dibenzofuran-substituted phenyl; a pyrimidine substituted with at least one of a biphenyl, phenyl-substituted naphthylene, dibenzofuran, dibenzothiophene, pyridine, terphenylene, phenalene, fluorene, or dibenzofuran-substituted phenyl; a quinazoline substituted with phenyl, biphenyl, or naphthyl; an isoquinoline substituted with phenyl; a 1,10-phenanthroline group; a pyridazine substituted with phenyl or naphthyl; a benzo[4,5] imidazo[1,2-f] phenanthridine group; a phenyl-substituted 1,3,4-oxadiazole; a phenyl-substituted 1,3,4-thiadiazole; a fluoranthene group; a dihydrophenoxazine group; or a dihydrophenothiazine group; R3 is hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted haloalkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group; c is an integer from 0 to 3; d is 1; m is an integer from 1 to 4; and when c and m are each independently 2 or more, the substituents in the parentheses are the same as or different from each other, with the proviso that the compound of Formula 2 in the second organic material layer does not include following compound: and wherein the first organic material layer comprises a compound selected from among the following compounds:
13 . The organic light emitting device of claim 12 , wherein Formula 2 is any one of the following Formulae 2-1 to 2-3: wherein in Formulae 2-1 to 2-3, R3, L4, Ar4, c, and d are the same as the definitions in Formula 2.
14 . The organic light emitting device of claim 12 , wherein L4 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group comprising N.
15 . The organic light emitting device of claim 12 , wherein the compound of Formula 2 is selected from among the following compounds:
16 . The organic light emitting device of claim 12 , wherein the first organic material layer is composed of one to three layers.
17 . The organic light emitting device of claim 16 , wherein: the first organic material layer comprises a hole adjusting layer; the hole adjusting layer comprises the compound of Formula 1; and when the hole adjusting layer is composed of two or more layers, the respective layers each independently include the compound of Formula 1 identically or differently.
18 . The organic light emitting device of claim 17 , wherein: the second organic material layer comprises an electron adjusting layer; and the electron adjusting layer comprises the compound of Formula 2.

Description

This application is a National Stage Application of International Application No. PCT/KR2019/002196 filed on Feb. 22, 2019, which claims priority to and the benefit of Korean Patent Application No. 10-2018-0022088 filed in the Korean Intellectual Property Office on Feb. 23, 2018, the entire contents of which are incorporated herein by reference. TECHNICAL FIELD Technical Field The present application relates to an organic light emitting device. Background In general, an organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy by using an organic material. An organic light emitting device using the organic light emitting phenomenon usually has a structure including a positive electrode, a negative electrode, and an organic material layer interposed therebetween. Here, the organic material layer has in many cases a multi-layered structure composed of different materials in order to improve the efficiency and stability of the organic light emitting device, and for example, can be composed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. In the structure of the organic light emitting device, if a voltage is applied between the two electrodes, holes are injected from the positive electrode into the organic material layer and electrons are injected from the negative electrode into the organic material layer, and when the injected holes and electrons meet each other, an exciton is formed, and light is emitted when the exciton falls down again to a ground state. There is a continuous need for developing a new material for the aforementioned organic light emitting device. BRIEF DESCRIPTION Technical Problem The present application has been made in an effort to provide an organic light emitting device. Technical Solution The present application provides an organic light emitting device including: a first electrode; a second electrode provided to face the first electrode; and a first organic material layer and a second organic material layer provided between the first electrode and the second electrode, in which the first organic material layer includes a compound of the following Formula 1, and the second organic material layer includes a compound of the following Formula 2: wherein in Formula 1:L1 to L3 are each independently a direct bond, or a substituted or unsubstituted arylene group;Ar1 to Ar3 are each independently hydrogen, deuterium, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group;R1 and R2 are each independently hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted haloalkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group;a and b are each independently an integer from 0 to 4;when a and b are each independently 2 or more, the substituents in the parenthesis are the same as or different from each other; wherein in Formula 2:L4 is a direct bond, a substituted or unsubstituted arylene group, or a substituted or unsubstituted divalent heterocyclic group;Ar4 is a substituted or unsubstituted aryl group, a substituted or unsubstituted phosphine oxide group, or a substituted or unsubstituted heterocyclic group;R3 is hydrogen, deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted haloalkyl group, a substituted or unsubstituted haloalkoxy group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group;c is an integer from 0 to 3;d is an integer from 1 to 2;m is an integer from 1 to 4; andwhen c, d, and m are each independently 2 or more, the substituents in the parenthesis are the same as or different from each other. Advantageous Effects An organic light emitting device using the compound according to an exemplary embodiment of the present application can implement a low driving voltage, high light emitting efficiency, or a long service life. BRIEF DESCRIPTION OF DRAWINGS FIG. 1 illustrates an example of an organic light emitting device in which a substrate 1, a positive electrode 2, a light emitting layer 3, and a negative electrode 4 are sequentially stacked. FIG. 2 illustrates an example of an organic light emitting device in which a substrate 1, a positive electrode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7, and a negative electrode 4 are sequentially stacked. FIG. 3 illustrates an example of an organic light emitting device in which a substrate 1, a posi