KR-102963086-B1 - COMPOUND FOR ORGANIC ELECTRIC ELEMENT, ORGANIC ELECTRIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF

KR102963086B1KR 102963086 B1KR102963086 B1KR 102963086B1KR-102963086-B1

Abstract

The present invention provides an organic electric device comprising a compound represented by Formula 1, a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, and an electronic device comprising the organic electric device. By including the compound represented by Formula 1 in the organic layer, the driving voltage of the organic electric device can be lowered and the luminous efficiency and lifespan can be improved.

Inventors

이세훈
조민지
이선희
문성윤
김원삼
김경철

Assignees

덕산네오룩스 주식회사

Dates

Publication Date: 20260512
Application Date: 20200820

Claims (13)

Compound represented by the following chemical formula 1: <Chemical Formula 1><Chemical Formula 1-1> In the above chemical formula 1, X1 , X2 , Y1 , and Y2 are independently single bonds, O, S, N(L-Ar), or C( R1 )( R2 ), provided that at least one of Y1 , Y2 , X1 , and X2 is a single bond, and m, n, o, and p are each 0 or 1, provided that m+n+o+p=3, and R1 to R4 , R1 and R2 are independently selected from the group consisting of hydrogen; deuterium; halogen; cyano group; nitro group; C6 – C60 aryl group; fluorenyl group; C2– C60 heterocyclic group comprising at least one heteroatom among O, N, S, Si and P; C3 – C60 aliphatic circular group; C1 – C30 alkyl group; C2 – C30 alkenyl group; C2 – C30 alkynyl group; C1 – C30 alkoxyl group; C6 – C30 aryloxy group; and Formula 1-1, and adjacent groups may bond to each other to form a ring, and R1 and R2 may bond to each other to form a ring, a, b, c, and d are each integers from 0 to 5, at least one of them is an integer of 1 or greater, and if each of them is an integer of 2 or greater, R 1 , R 2 , R 3 , and R 4 are each the same or different from each other, L' and L are independently selected from the group consisting of single bonds; C6 – C60 arylene groups; fluorenylene groups; C3 – C60 aliphatic groups; and C2 – C60 heterocyclic groups comprising at least one heteroatom among O, N, S, Si, and P, and Ar 1 and Ar 2 are independently selected from the group consisting of C 6 –C 60 aryl groups; fluorenyl groups; C 2 –C 60 heterocyclic groups containing at least one heteroatom among O, N, S, Si and P; and C 3 –C 60 aliphatic groups, and Ar is independently selected from the group consisting of C1 – C30 alkyl groups; C2 – C30 alkenyl groups; C2 – C30 alkynyl groups; C6 – C60 aryl groups; fluorenyl groups; C2–C60 heterocyclic groups comprising at least one heteroatom among O, N, S, Si, and P; and C3 – C60 aliphatic groups, z1 is an integer from 0 to 5 and z2 is an integer from 0 to 3, and where each of these is an integer greater than or equal to 2, L', Ar 1 , and Ar 2 are each equal to or different from each other, and The above aryl group, arylene group, fluorenyl group, fluorenyllene group, heterocyclic group, aliphatic cyclic group, alkyl group, alkenyl group, alkynyl group, alkoxyl group, aryloxy group, and the ring formed by bonding adjacent groups together are each deuterium; halogen; a silane group substituted or unsubstituted with a C1 - C20 alkyl group or a C6 - C20 aryl group; a phosphine oxide substituted or unsubstituted with a C1 - C20 alkyl group or a C6 - C20 aryl group; a siloxane group; a cyano group; a nitro group; a C1 - C20 alkylthio group; a C1 - C20 alkoxyl group; a C6 - C20 aryloxy group; a C6 - C20 arylthio group; a C1 - C20 alkyl group; It may be substituted with one or more substituents selected from the group consisting of a C2 - C20 alkenyl group; a C2 - C20 alkyneyl group; a C6 - C20 aryl group; a fluoreneyl group; a C2- C20 heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; a C3-C20 aliphatic heterocyclic group ; and combinations thereof.
In Article 1, A compound characterized in that the above chemical formula 1 is represented by one of the following chemical formulas: <Chemical Formula 2><Chemical Formula 3><Chemical Formula 4> <Chemical Formula 5><Chemical Formula 7> In the above chemical formula, X₁ , X₂ , Y₁ , Y₂ , R₁ - R₄ are as defined in claim 1, and In Chemical Formula 2, a is an integer of 0-3, b is 0-4, c is 0-3, and d is 0-4; in Chemical Formula 3, a is an integer of 0-3, b is 0-3, c is 0-4, and d is 0-4; in Chemical Formula 4, a is an integer of 0-4, b is 0-3, c is 0-4, and d is 0-3; in Chemical Formula 5, a is an integer of 0-4, b is 0-3, c is 0-4, and d is 0-3; and in Chemical Formula 7, a is an integer of 0-3, b is 0-4, c is 0-3, and d is 0-4.
In Article 1, A compound characterized by the above chemical formula 1-1 being represented by the following chemical formula 1-1-A or chemical formula 1-1-B: <Chemical Formula 1-1-A><Chemical Formula 1-1-B> In the above chemical formulas 1-1-A and 1-1-B, L', Ar 1 and Ar 2 are as defined in claim 1.
In Paragraph 3, A compound characterized in that at least one of Ar 1 and Ar 2 is represented by the following chemical formula 1-a or chemical formula 1-b: <Chemical Formula 1-a><Chemical Formula 1-b> In the above chemical formulas 1-a and 1-b, Z1 and Z2 are independently single bonds, O, S, N( L1 - Ar1 ) or C(R')(R"), and R a , R b , R c , R d , R' and R" are independently hydrogen; deuterium; halogen; a silane group substituted or unsubstituted with a C1 - C20 alkyl group or a C6 - C20 aryl group; a phosphine oxide substituted or unsubstituted with a C1 - C20 alkyl group or a C6 - C20 aryl group; a siloxane group; a cyano group; a nitro group; a C1 - C20 alkylthio group; a C1 - C20 alkoxyl group; a C6 - C20 aryloxy group; a C6 - C20 arylthio group; a C1 - C20 alkyl group; a C2 - C20 alkenyl group; a C2 - C20 alkynyl group; a C6 - C20 aryl group; Selected from the group consisting of a fluorene monogroup; a C2 - C20 heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si, and P; and an aliphatic group of C3 - C20 , wherein adjacent groups can bond with each other to form a ring, and R' and R" can bond with each other to form a ring, and e is an integer from 0 to 3, and f, g, and h are each integers from 0 to 4, and if each of these is an integer greater than or equal to 2, then R a , R b , R c , and R d are each equal to or different from each other, and The above L1 is selected from the group consisting of a single bond; a C6 - C20 arylene group; a fluorenylene group; a C2 - C20 heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si, and P; and a C3 - C20 aliphatic group, and The above Ar 1 is selected from the group consisting of a C 6 -C 20 aryl group; a fluorenyl group; a C 2 -C 20 heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P; and an aliphatic group of C 3 -C 20 .
In Article 1, A compound characterized by being one of the following compounds, represented by the above chemical formula 1: .
An organic electric device comprising a first electrode, a second electrode, and an organic layer formed between the first electrode and the second electrode, An organic electric device characterized in that the above organic layer comprises a compound represented by the chemical formula 1 of claim 1.
In Paragraph 6, An organic electric device characterized by further including a light efficiency improvement layer formed on the surface of the first electrode and the second electrode that does not come into contact with the organic layer.
In Paragraph 6, An organic electric device characterized in that the compound represented by the above chemical formula 1 is included in the light-emitting layer of the organic layer.
In Article 7, An organic electric device characterized in that the light efficiency improving layer comprises a compound represented by the chemical formula 1.
In Paragraph 6, An organic electric device characterized in that the above organic layer comprises two or more stacks including a hole transport layer, a light-emitting layer, and an electron transport layer sequentially formed on the first electrode.
In Article 10, An organic electric device characterized in that the above organic layer further comprises a charge generating layer formed between the two or more stacks.
A display device comprising the organic electric element of claim 6; and An electronic device comprising a control unit for driving the above-mentioned display device.
In Paragraph 12, An electronic device characterized in that the above-mentioned organic electric device is selected from the group consisting of organic electroluminescent devices, organic solar cells, organic photosensitive materials, organic transistors, devices for monochromatic lighting, and devices for quantum dot displays.

Description

Compound for organic electric element, organic electric element using the same, and electronic device thereof The present invention relates to a compound for an organic electric device, an organic electric device using the same, and an electronic device thereof. In general, organic light emission refers to the phenomenon of converting electrical energy into light energy using organic materials. Organic electrical devices utilizing organic light emission typically have a structure that includes an anode, a cathode, and an organic layer between them. Here, the organic layer is often composed of a multilayer structure made of different materials to increase the efficiency and stability of the organic electrical device, and may consist of, for example, a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, and an electron injection layer. The biggest issues regarding organic electroluminescent devices are lifespan and efficiency, and as displays become larger in size, these efficiency and lifespan issues must be resolved. Efficiency, lifespan, and driving voltage are interrelated; as efficiency increases, the driving voltage relatively decreases, and as the driving voltage drops, the crystallization of organic materials caused by Joule heating during operation is reduced, resulting in a tendency for increased lifespan. However, simply improving the aforementioned organic layers does not guarantee maximum efficiency. This is because both long lifespan and high efficiency can be achieved simultaneously when the energy levels and T1 values between the organic layers, along with the intrinsic properties of the materials (mobility, interfacial characteristics, etc.), form an optimal combination. Furthermore, in order to solve the light emission problem in the hole transport layer of recent organic electroluminescent devices, an auxiliary light emission layer must exist between the hole transport layer and the light-emitting layer, and it is necessary to develop different auxiliary light emission layers according to each light-emitting layer (R, G, B). FIGS. 1 to 3 are exemplary diagrams of an organic electroluminescent device according to the present invention. Unless otherwise stated, the terms "aryl group" and "arylene group" used in the present invention each have 6 to 60 carbon atoms, but are not limited thereto. In the present invention, the aryl group or arylene group may include a monocyclic type, a ring assembly, a conjugated multi-ring system, a spiro compound, etc. Additionally, unless otherwise stated in this specification, the aryl group may include a fluorenyl group and the arylene group may include a fluorenyl group. The term "fluorenyl group" used in the present invention refers to a substituted or unsubstituted fluorenyl group, and "fluorenyl group" refers to a substituted or unsubstituted fluorenyl group. The fluorenyl group or fluorenyl group used in the present invention includes a spiro compound formed by R and R' being bonded to each other in the following structure, and also includes a compound in which neighboring R' are bonded to each other to form a ring. "Substituted fluorenyl group" and "substituted fluorenyl group" mean that at least one of R, R', and R" in the following structure is a substituent other than hydrogen, and in the chemical formula below, R" may be 1 to 8. In this specification, regardless of valence, fluorenyl group, fluorenyl group, fluorentriyl group, etc. may all be referred to as fluoren groups. The term "spiro compound" used in the present invention has a "spiro linkage," and a spiro linkage refers to a connection formed by two rings sharing only one atom. At this time, the atom shared between the two rings is called a "spiro atom," and depending on the number of spiro atoms contained in a compound, they are respectively called "monospiro-," "diespiro-," and "trispiro-" compounds. The term "heterocyclic group" as used in the present invention includes not only aromatic rings such as "heteroaryl groups" or "heteroarylene groups" but also non-aromatic rings, and unless otherwise noted, refers to a ring having 2 to 60 carbon atoms containing one or more heteroatoms, but is not limited thereto. Unless otherwise noted, the term "heteroatom" as used in this specification refers to an element other than carbon, such as N, O, S, P, or Si, and may include heteroatom groups such as SO₂ , P=O, etc., as in the following compounds, instead of carbons forming the ring. In this specification, heterocyclic groups include single-ring types containing heteroatoms, ring assemblies, conjugated multi-ring systems, spiro compounds, etc. The term "aliphatic ring" as used in the present invention refers to a cyclic hydrocarbon excluding aromatic hydrocarbons, and includes monocyclic types, ring aggregates, conjugated multi-ring systems, spiro compounds, etc. Unless otherwise stated, it refers to a ring having 3 to 60 carbon atoms, but is not limit