KR-102960754-B1 - LIGHT EMITTING DEVICE, DISPLAY DEVICE, AND AMINE COMPOUND FOR LIGHT EMITTING DEVICE

KR102960754B1KR 102960754 B1KR102960754 B1KR 102960754B1KR-102960754-B1

Abstract

A light-emitting element according to one embodiment of the present invention comprises a first electrode, a second electrode disposed on the first electrode, and at least one functional layer disposed between the first electrode and the second electrode and comprising an amine compound represented by Formula 1. [Chemical Formula 1]

Inventors

김채영
김민지
김범준
유병욱
이정민
정은재
조소희
차한나
한상현

Assignees

삼성디스플레이 주식회사

Dates

Publication Date: 20260507
Application Date: 20230622

Claims (20)

First electrode; A second electrode facing the first electrode; and It includes a functional layer disposed between the first electrode and the second electrode, and The above functional layer is a light-emitting element comprising an amine compound represented by the following chemical formula 5: [Chemical Formula 5] In the above chemical formula 5, n3, n4, and n5 are each independently integers from 0 to 4, and n6 is an integer between 0 and 5 inclusive, and n10, n11, and n20 are each independently 0 or 1, and n10, n11, and n20 are not simultaneously 0, If n10 is 1, then n11 is also 1, and X is O, S, NR 2 or CR 3 R 4 , and A is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and R1 is a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, and R2 , R3 , and R4 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and Q 10 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and Q 11 and Q 20 are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, and Q3 , Q4 , Q5 , and Q6 are each independently hydrogen atoms or deuterium atoms.
In paragraph 1, The above functional layer The light-emitting layer, a hole transport region disposed between the first electrode and the light-emitting layer, and an electron transport region disposed between the light-emitting layer and the second electrode, are included. The above hole transport region is a light-emitting device comprising an amine compound represented by the above chemical formula 5.
In paragraph 2, The above hole transport region is A hole injection layer disposed between the first electrode and the light-emitting layer, and It includes a hole transport layer disposed between the hole injection layer and the light-emitting layer, and A light-emitting device comprising at least one of the hole injection layer and the hole transport layer, wherein the amine compound represented by the chemical formula 5 is included.
In paragraph 3, The above hole transport region is It further includes an electron blocking layer disposed between the hole transport layer and the light-emitting layer, and A light-emitting device comprising at least one of the hole injection layer, the hole transport layer, and the electron blocking layer, wherein the amine compound represented by the chemical formula 5.
In paragraph 1, A light-emitting device in which the amine compound represented by the above chemical formula 5 is a monoamine compound.
In paragraph 1, The amine compound represented by the above chemical formula 5 is a light-emitting device represented by the following chemical formula 1-1: [Chemical Formula 1-1] In the above chemical formula 1-1, n3 to n6, n10, n11, n20, X, A, R1, Q3 to Q6 , Q10 , Q11 , and Q20 are the same as defined in the description of Chemical Formula 5 above.
In paragraph 1, The amine compound represented by the above chemical formula 5 is a light-emitting device represented by either the following chemical formula 2-2 or the following chemical formula 2-3: [Chemical Formula 2-2] [Chemical Formula 2-3] In the above chemical formula 2-2 and the above chemical formula 2-3, n3 to n6, n10, n11, n20, X, A, R1, Q3 to Q6 , Q10 , Q11 , and Q20 are the same as defined in the description of Chemical Formula 5 above.
In paragraph 1, The amine compound represented by the above chemical formula 5 is a light-emitting device represented by either the following chemical formula 3-2 or the following chemical formula 3-3: [Chemical Formula 3-2] [Chemical Formula 3-3] In the above chemical formulas 3-2 and 3-3, R 2a is a hydrogen atom, a deuterium atom, an unsubstituted alkyl group having 1 to 30 carbon atoms, or an unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, and n3 to n6, n10, n11, n20, A, R1 , Q3 to Q6 , Q10 , Q11 , and Q20 are the same as defined in the description of Chemical Formula 5 above.
In paragraph 1, The amine compound represented by the above chemical formula 5 is a light-emitting device represented by the following chemical formula 4: [Chemical Formula 4] In the above chemical formula 4, n3 to n6, n10, n11, n20, X, R1 , Q3 to Q6 , Q10 , Q11 , and Q20 are the same as defined in the description of Chemical Formula 5 above.
In Paragraph 9, The amine compound represented by the above chemical formula 4 is a light-emitting device represented by the following chemical formula 4-1: [Chemical Formula 4-1] In the above chemical formula 4-1, n3 to n6, n10, n11, n20, X, R1 , Q3 to Q6 , Q10 , Q11 , and Q20 are the same as defined in the description of Chemical Formula 5 above.
In paragraph 1, In the above chemical formula 5, R1 is a light-emitting element in which is a substituted or unsubstituted cyclohexyl group, a substituted or unsubstituted bicycloheptanyl group, or a substituted or unsubstituted adamantyl group.
delete
In paragraph 1, In the above chemical formula 5, Q 10 is a substituted or unsubstituted methyl group, and Q 11 and Q 20 are each independently a substituted or unsubstituted methyl group, or a substituted or unsubstituted phenyl group, in a light-emitting device.
In paragraph 1, An amine compound represented by the above chemical formula 5 is a light-emitting device represented by any one of the compounds listed in compound group 1 below: [Compound Group 1] .
Base layer; A circuit layer disposed on the above base layer; and It includes a display element layer disposed on the above circuit layer and including a light-emitting element, and A display device comprising: a first electrode, a second electrode disposed on the first electrode, and a hole transport region disposed between the first electrode and the second electrode and comprising an amine compound represented by the following chemical formula 5; [Chemical Formula 5] In the above chemical formula 5, n3, n4, and n5 are each independently integers from 0 to 4, and n6 is an integer between 0 and 5 inclusive, and n10, n11, and n20 are each independently 0 or 1, and n10, n11, and n20 are not simultaneously 0, If n10 is 1, then n11 is also 1, and X is O, S, NR 2 or CR 3 R 4 , and A is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and R1 is a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, and R2 , R3 , and R4 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and Q 10 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and Q 11 and Q 20 are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, and Q3 , Q4 , Q5 , and Q6 are each independently hydrogen atoms or deuterium atoms.
Amine compound represented by the following chemical formula 5: [Chemical Formula 5] In the above chemical formula 5, n3, n4, and n5 are each independently integers from 0 to 4, and n6 is an integer between 0 and 5 inclusive, and n10, n11, and n20 are each independently 0 or 1, and n10, n11, and n20 are not simultaneously 0, If n10 is 1, then n11 is also 1, and X is O, S, NR 2 or CR 3 R 4 , and A is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms, and R1 is a substituted or unsubstituted cycloalkyl group having 3 to 10 carbon atoms, and R2 , R3 , and R4 are each independently a hydrogen atom, a deuterium atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, and Q 10 is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and Q 11 and Q 20 are each independently a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, and Q3 , Q4 , Q5 , and Q6 are each independently hydrogen atoms or deuterium atoms.
In Paragraph 16, The amine compound represented by the above chemical formula 5 is the amine compound represented by the following chemical formula 1-1: [Chemical Formula 1-1] In the above chemical formula 1-1, n3 to n6, n10, n11, n20, X, A, R1, Q3 to Q6 , Q10 , Q11 , and Q20 are the same as defined in the description of Chemical Formula 5 above.
In Paragraph 16, The amine compound represented by the above chemical formula 5 is an amine compound represented by either the following chemical formula 2-2 or the following chemical formula 2-3: [Chemical Formula 2-2] [Chemical Formula 2-3] In the above chemical formula 2-2 and the above chemical formula 2-3, n3 to n6, n10, n11, n20, X, A, R1, Q3 to Q6 , Q10 , Q11 , and Q20 are the same as defined in the description of Chemical Formula 5 above.
In Paragraph 16, The amine compound represented by the above chemical formula 5 is an amine compound represented by either the following chemical formula 3-2 or the following chemical formula 3-3: [Chemical Formula 3-2] [Chemical Formula 3-3] In the above chemical formulas 3-2 and 3-3, R 2a is a hydrogen atom, a deuterium atom, an unsubstituted alkyl group having 1 to 30 carbon atoms, or an unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, and n3 to n6, n10, n11, n20, A, R1 , Q3 to Q6 , Q10 , Q11 , and Q20 are the same as defined in the description of Chemical Formula 5 above.
In Paragraph 16, The amine compound represented by the above chemical formula 5 is an amine compound represented by any one of the compounds of compound group 1 below: [Compound Group 1] .

Description

Light-emitting device, display device, and amine compound for light-emitting device The present invention relates to a light-emitting element, a display device, and an amine compound used in the light-emitting element. Recently, there has been active development of organic electroluminescence displays as image display devices. Unlike liquid crystal displays, organic electroluminescence displays are so-called self-emissive display devices that realize a display by causing a light-emitting material containing an organic compound in the light-emitting layer to emit light by recombining holes and electrons injected from a first electrode and a second electrode in the light-emitting layer. In applying organic light-emitting diodes to display devices, there is a demand for lower driving voltage, higher luminous efficiency, and longer lifespan of the devices, and there is a continuous demand for the development of materials for organic light-emitting diodes that can stably realize these requirements. In addition, development of hole transport layer materials is underway to realize high-efficiency organic electroluminescent devices. FIG. 1 is a plan view of a display device according to one embodiment of the present invention. FIG. 2 is a cross-sectional view of a display device according to one embodiment of the present invention. FIG. 3 is a cross-sectional view schematically showing a light-emitting element according to one embodiment of the present invention. FIG. 4 is a cross-sectional view schematically showing a light-emitting element according to one embodiment of the present invention. FIG. 5 is a cross-sectional view schematically showing a light-emitting element according to one embodiment of the present invention. FIG. 6 is a cross-sectional view schematically showing a light-emitting element according to one embodiment of the present invention. FIGS. 7 and FIGS. 8 are cross-sectional views of a display device according to one embodiment of the present invention. FIG. 9 is a cross-sectional view showing a display device according to one embodiment of the present invention. FIG. 10 is a cross-sectional view showing a display device according to one embodiment of the present invention. FIG. 11 is a drawing showing a vehicle with a display device installed according to one embodiment of the present invention. The present invention is capable of various modifications and may take various forms, and specific embodiments are illustrated in the drawings and described in detail in the text. However, this is not intended to limit the invention to the specific disclosed forms, and it should be understood that the invention includes all modifications, equivalents, and substitutions that fall within the spirit and scope of the invention. In describing each drawing, similar reference numerals have been used for similar components. In the attached drawings, the dimensions of the structures are depicted enlarged from their actual size for clarity of the invention. Terms such as "first," "second," etc., may be used to describe various components, but said components should not be limited by said terms. These terms are used solely for the purpose of distinguishing one component from another. For example, without departing from the scope of the invention, the first component may be named the second component, and similarly, the second component may be named the first component. A singular expression includes a plural expression unless the context clearly indicates otherwise. In this application, terms such as "comprising" or "having" are intended to specify the existence of the features, numbers, steps, actions, components, parts, or combinations thereof described in the specification, and should be understood as not precluding the existence or addition of one or more other features, numbers, steps, actions, components, parts, or combinations thereof. In this application, when a part such as a layer, film, region, or plate is described as being "on" or "upper" to another part, this includes not only cases where it is "immediately above" the other part, but also cases where there is another part in between. Conversely, when a part such as a layer, film, region, or plate is described as being "under" or "lower" to another part, this includes not only cases where it is "immediately below" the other part, but also cases where there is another part in between. Furthermore, in this application, being "placed on" may include cases where it is placed not only on the upper part but also on the lower part. In this specification, "substituted or unsubstituted" may mean substituted or unsubstituted with one or more substituents selected from the group consisting of deuterium atoms, halogen atoms, cyano groups, nitro groups, amino groups, silyl groups, oxy groups, thio groups, sulfinyl groups, sulfonyl groups, carbonyl groups, boron groups, phosphine oxide groups, phosphine sulfide groups, alkyl groups, alkenyl groups, alkynyl groups