Organic compounds and organic electroluminescent devices comprising the same

Abstract

The present application relates to a novel organic compound and an organic light emitting device comprising the same, and more particularly, to an organic electroluminescent device which significantly improves low driving voltage, luminous efficiency, and lifespan.

Description

Technical Field

[0001] This invention relates to organic compounds and organic electroluminescent devices containing the same. Background Technology

[0002] Compared to other flat panel display devices such as liquid crystal displays (LCDs), plasma display panels (PDPs), and field emission displays (FEDs), organic electroluminescent devices have many advantages in terms of simple structure and manufacturing process. They not only have excellent characteristics in terms of high brightness and viewing angle, but also have a fast response speed and low driving voltage, making them widely used in flat panel displays such as wall-mounted televisions (TVs) or as light sources for backlighting, illumination, billboards, etc.

[0003] Typically, when a voltage is applied to an organic electroluminescent device, holes injected from the anode and electrons injected from the cathode recombine to form excitons, which are then converted into light as their energy is transferred to the light-emitting material.

[0004] To improve the efficiency and stability of organic electroluminescent devices, since Tang et al. of Eastman Kodak disclosed a low-voltage driven organic electroluminescent device that forms a stacked organic thin film between two opposing electrodes (CWTang, SAVanslyke, Applied Physics Letters, Vol. 51, p. 913, 1987), research on organic materials for multilayer thin film structure organic electroluminescent devices has been ongoing.

[0005] Typically, an organic electroluminescent device includes a cathode (electron injection electrode), an anode (hole injection electrode), and one or more organic layers disposed between the two electrodes. In this case, the organic electroluminescent device has a hole injection layer (HIL), a hole transport layer (HTL), a light emitting layer (EML), an electron transport layer (ETL), or an electron injection layer (EIL) stacked sequentially from the anode. To improve the efficiency of the light emitting layer, an electron blocking layer (EBL) or a hole blocking layer (HBL) can be added before and after each light emitting layer.

[0006] The reason for fabricating this organic electroluminescent device into a multilayer thin film structure is to improve the interfacial stability between the electrode and the organic material and to increase the luminous efficiency.

[0007] In particular, when organic compounds are used as multilayer thin film materials, since the movement speeds of holes and electrons vary greatly depending on their characteristics, hole transport layers and electron transport layers containing appropriate compounds should be used to effectively transport holes and electrons to the light-emitting layer. Furthermore, the luminous efficiency can be significantly improved by achieving a density balance between holes and electrons.

[0008] Therefore, the characteristics of the organic compounds contained in each layer of the organic thin film not only have a significant impact on the device's driving voltage, luminous efficiency, brightness, and lifespan, but also affect the efficiency or lifespan of the final manufactured display. Thus, using specific organic materials suitable for multilayer structures in organic electroluminescent devices is particularly important. Therefore, it is currently necessary to actively study the composition of each layer of the organic thin film.

[0009] Existing technical documents

[0010] Patent documents

[0011] Patent Document 1: US8207526B2

[0012] Patent Document 2: KR10-2019-0128179A Summary of the Invention

[0013] Technical issues

[0014] The purpose of this invention is to provide an organic electroluminescent device that not only contains a novel organic compound, but also has low driving voltage, excellent device efficiency, and longevity characteristics.

[0015] Technical solution

[0016] To achieve the above objectives, the compounds provided by this invention can be represented by the following chemical formula 1:

[0017] Chemical Formula 1

[0018]

[0019] Where n is an integer from 0 to 8,

[0020] m and q may be the same or different, and each is an independent integer from 0 to 4.

[0021] p is an integer from 0 to 2.

[0022] X is O or S.

[0023] L1 to L3 may be the same or different, and are independently selected from the group consisting of single bonds, aryl groups with 6 to 30 substituted or unsubstituted carbon atoms, heteroaryl groups with 1 to 30 substituted or unsubstituted carbon atoms, alkyl groups with 1 to 10 substituted or unsubstituted carbon atoms, cycloalkyl groups with 3 to 10 substituted or unsubstituted carbon atoms, alkenyl groups with 2 to 10 substituted or unsubstituted carbon atoms, cycloalkenyl groups with 3 to 10 substituted or unsubstituted carbon atoms, heteroalkyl groups with 1 to 10 substituted or unsubstituted carbon atoms, heterocycloalkyl groups with 2 to 10 substituted or unsubstituted carbon atoms, heteroalkenyl groups with 2 to 10 substituted or unsubstituted carbon atoms, and heterocycloalkenyl groups with 2 to 10 substituted or unsubstituted carbon atoms.

[0024] Ar1 and Ar2 may be the same or different, and are independently selected from the group consisting of aryl groups with 6 to 30 substituted or unsubstituted carbon atoms, heteroaryl groups with 1 to 30 substituted or unsubstituted carbon atoms, alkyl groups with 1 to 20 substituted or unsubstituted carbon atoms, cycloalkyl groups with 3 to 20 substituted or unsubstituted carbon atoms, heteroalkyl groups with 1 to 20 substituted or unsubstituted carbon atoms, heterocycloalkyl groups with 2 to 20 substituted or unsubstituted carbon atoms, aralkyl groups with 6 to 30 substituted or unsubstituted carbon atoms, alkenyl groups with 2 to 20 substituted or unsubstituted carbon atoms, cycloalkenyl groups with 3 to 20 substituted or unsubstituted carbon atoms, and heteroalkenyl groups with 2 to 20 substituted or unsubstituted carbon atoms.

[0025] R1 to R4 may be the same or different, and are independently selected from hydrogen, deuterium, cyano, nitro, halogen, hydroxyl, substituted or unsubstituted alkylthio group with 1 to 4 carbon atoms, substituted or unsubstituted alkyl group with 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group with 3 to 20 carbon atoms, substituted or unsubstituted alkenyl group with 2 to 30 carbon atoms, substituted or unsubstituted alkynyl group with 2 to 24 carbon atoms, substituted or unsubstituted aralkyl group with 7 to 30 carbon atoms, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group with 1 to 60 carbon atoms, etc. The group consisting of heteroaryl groups having 2 to 30 substituted or unsubstituted carbon atoms, alkoxy groups having 1 to 30 substituted or unsubstituted carbon atoms, alkylamino groups having 1 to 30 substituted or unsubstituted carbon atoms, arylamino groups having 6 to 30 substituted or unsubstituted carbon atoms, arylalkylamino groups having 7 to 30 substituted or unsubstituted carbon atoms, heteroarylamino groups having 1 to 24 substituted or unsubstituted carbon atoms, alkylsilyl groups having 1 to 30 substituted or unsubstituted carbon atoms, arylsilyl groups having 6 to 30 substituted or unsubstituted carbon atoms, and aryloxy groups having 6 to 30 substituted or unsubstituted carbon atoms.

[0026] Furthermore, the organic electroluminescent device provided by the present invention includes: a first electrode; a second electrode disposed opposite to the first electrode; and one or more organic layers disposed between the first electrode and the second electrode, wherein the one or more organic layers contain a compound represented by the above chemical formula 1.

[0027] In this invention, unless otherwise defined, “hydrogen” means hydrogen, protium, deuterium or tritium.

[0028] In this invention, "halogen group" refers to fluorine, chlorine, bromine or iodine.

[0029] In this invention, "alkyl" refers to a monovalent substituent derived from a straight-chain or branched saturated hydrocarbon having 1 to 40 carbon atoms. As an example, it can be methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, isopentyl, hexyl, etc., but is not limited thereto.

[0030] In this invention, "alkenyl" refers to a monovalent substituent derived from a straight-chain or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples include vinyl, allyl, isopropenyl, 2-butenyl, etc., but it is not limited to these.

[0031] In this invention, "alkynyl" refers to a monovalent substituent derived from a straight-chain or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples include ethynyl and 2-propynyl, but it is not limited to these.

[0032] In this invention, "alkylthio" refers to the alkyl group described above that is bonded by a sulfur bond (-S-).

[0033] In this invention, "aryl" refers to a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, formed by the combination of a single ring or two or more rings. Furthermore, it can include forms where two or more rings are simply attached to each other or fused together; specifically, it can be naphthyl, anthraceneyl, phenanthryl, triphenyl, pyrene, finadeninyl, perylene, etc. Fluoryl groups, fluorene groups, etc., but not limited to these. The aforementioned fluorene groups can be substituted, and adjacent groups can simply attach to form a ring.

[0034] In this invention, "heteroaryl" refers to a monovalent substituent derived from a mono-heterocyclic or polycyclic aromatic hydrocarbon having 6 to 30 carbon atoms. In this case, one or more carbons of the ring are substituted by heteroatoms, preferably 1 to 3 carbons are substituted by heteroatoms such as N, O, S, or Se. Furthermore, it can include forms where two or more rings are simply attached or fused, and can also include forms fused with an aryl group. Examples of such heteroaryl groups include six-membered monocyclic groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, and triazinyl; polycyclic groups such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, and carbazolyl; and polycyclic groups such as 2-furanyl, N-imidazoyl, 2-isooxazolyl, 2-pyridinyl, and 2-pyrimidinyl, but are not limited thereto.

[0035] In this invention, "aryloxy group" refers to a monovalent substituent represented by RO-, where R refers to an aryl group having 6 to 60 carbon atoms. Examples of such aryloxy groups include phenoxy, naphthoxy, diphenoxy, etc., but it is not limited to these.

[0036] In this invention, "alkoxy" refers to a monovalent substituent represented by R'O-, where R' refers to an alkyl group having 1 to 40 carbon atoms, and may include linear, branched, or cyclic structures. Examples of alkoxy groups include methoxy, ethoxy, n-propoxy, 1-propoxy, tert-butoxy, n-butoxy, pentoxy, etc., but are not limited thereto.

[0037] In this invention, "alkoxy" can be straight-chain, branched, or cyclic. There is no particular limitation on the number of carbon atoms in the alkoxy group; preferably, the number of carbon atoms is 1 to 20. Specifically, it can be methoxy, ethoxy, n-propoxy, isopropoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentoxy, neopentoxy, isopentoxy, n-hexyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, n-octoxy, n-nonoxy, n-decoxy, benzyloxy, p-methylbenzyloxy, etc., but is not limited to these.

[0038] In this invention, "aralkyl" refers to aryl and alkyl groups as described above. Preferably, aralkyl includes lower alkyl groups. Non-limiting examples of suitable aralkyl groups include benzyl, 2-phenylethyl, and naphthylmethyl. Bonding to a residue is achieved via an alkyl group.

[0039] In this invention, "aromatic amino" refers to an amino group substituted with an aryl group having 6 to 30 carbon atoms.

[0040] In this invention, "alkylamino" refers to an amino group that has been substituted by an alkyl group having 1 to 30 carbon atoms.

[0041] In this invention, "aromatic amino" refers to an amino group substituted with an aryl-alkyl group having 6 to 30 carbon atoms.

[0042] In this invention, "heteroaromatic amino" refers to an amino group substituted with aryl and heterocyclic groups having 6 to 30 carbon atoms.

[0043] In this invention, "heteroalkyl" refers to an aryl-alkyl group that has been substituted with a heterocyclic group.

[0044] In this invention, "cycloalkyl" refers to a first-order substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, etc., but are not limited thereto.

[0045] In this invention, "heterocyclic alkyl" refers to a first-order substituent derived from a non-aromatic hydrocarbon having 3 to 40 carbon atoms, wherein one or more carbon atoms in the ring are replaced by heteroatoms, preferably, one to three carbon atoms are replaced by heteroatoms such as N, O, S or Se. Examples of such heterocyclic alkyl groups include morpholine, piperazine, etc., but it is not limited to these.

[0046] In this invention, "alkylsilyl" refers to a silyl group substituted with an alkyl group having 1 to 40 carbon atoms, and "arylsilyl" refers to a silyl group substituted with an aryl group having 6 to 60 carbon atoms.

[0047] In this invention, "fused ring" refers to a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring, a fused heteroaromatic ring, or a combination thereof.

[0048] In this invention, "forming a ring by bonding with an adjacent group" means forming the following by bonding with an adjacent group: a substituted or unsubstituted aliphatic hydrocarbon ring; a substituted or unsubstituted aromatic hydrocarbon ring; a substituted or unsubstituted aliphatic heterocycle; a substituted or unsubstituted aromatic heterocycle; or a fused ring thereof.

[0049] In this invention, an example of an "aromatic hydrocarbon ring" may be phenyl, naphthyl, anthracene, etc., but it is not limited to this.

[0050] In this invention, "aliphatic heterocycle" refers to an aliphatic ring that includes one or more heteroatoms.

[0051] In this invention, "aromatic heterocycle" refers to an aromatic ring that includes one or more heteroatoms.

[0052] In this invention, "substitution" refers to the replacement of a hydrogen atom bonded to a carbon atom of the compound with another substituent. The position of substitution refers to the location where the hydrogen atom is replaced; that is, there are no particular restrictions as long as the substituent can be substituted. When substituted by two or more substituents, the two or more substituents can be the same or different. The substituents can be selected from hydrogen, cyano, nitro, halogen, hydroxyl, alkyl with 1 to 30 carbon atoms, alkenyl with 2 to 30 carbon atoms, alkynyl with 2 to 24 carbon atoms, heteroalkyl with 2 to 30 carbon atoms, aralkyl with 6 to 30 carbon atoms, aryl with 5 to 30 carbon atoms, heteroaryl with 2 to 30 carbon atoms, heteroaryl with 3 to 30 carbon atoms, alkoxy with 1 to 30 carbon atoms, and carbon atom... The substance may be substituted with one or more of the following groups: alkylamino with 1 to 30 carbon atoms, aromaticamino with 6 to 30 carbon atoms, aromaticalkylamino with 6 to 30 carbon atoms, heteroaromaticamino with 2 to 24 carbon atoms, substituted or unsubstituted alkylsilyl with 1 to 30 carbon atoms, substituted or unsubstituted arylsilyl with 6 to 30 carbon atoms, and substituted or unsubstituted aryloxy with 6 to 30 carbon atoms, but is not limited to the examples described above.

[0053] The effects of the invention

[0054] As a novel organic compound, this invention, when used as a material for organic electroluminescent devices, not only achieves excellent interfacial properties with adjacent layers, but also possesses excellent chemical stability.

[0055] Furthermore, the organic electroluminescent device provided by the present invention contains the aforementioned novel organic compound, and therefore has low driving voltage, excellent device efficiency, and lifetime characteristics. Detailed Implementation

[0056] The compounds provided by this invention are represented by the following chemical formula 1:

[0057] Chemical Formula 1

[0058]

[0059] Where n is an integer from 0 to 8,

[0060] m and q may be the same or different, and each is an independent integer from 0 to 4.

[0061] p is an integer from 0 to 2.

[0062] X is O or S.

[0063] L1 to L3 may be the same or different, and are independently selected from the group consisting of single bonds, aryl groups with 6 to 30 substituted or unsubstituted carbon atoms, heteroaryl groups with 1 to 30 substituted or unsubstituted carbon atoms, alkyl groups with 1 to 10 substituted or unsubstituted carbon atoms, cycloalkyl groups with 3 to 10 substituted or unsubstituted carbon atoms, alkenyl groups with 2 to 10 substituted or unsubstituted carbon atoms, cycloalkenyl groups with 3 to 10 substituted or unsubstituted carbon atoms, heteroalkyl groups with 1 to 10 substituted or unsubstituted carbon atoms, heterocycloalkyl groups with 2 to 10 substituted or unsubstituted carbon atoms, heteroalkenyl groups with 2 to 10 substituted or unsubstituted carbon atoms, and heterocycloalkenyl groups with 2 to 10 substituted or unsubstituted carbon atoms.

[0064] Ar1 and Ar2 may be the same or different, and are independently selected from the group consisting of aryl groups with 6 to 30 substituted or unsubstituted carbon atoms, heteroaryl groups with 1 to 30 substituted or unsubstituted carbon atoms, alkyl groups with 1 to 20 substituted or unsubstituted carbon atoms, cycloalkyl groups with 3 to 20 substituted or unsubstituted carbon atoms, heteroalkyl groups with 1 to 20 substituted or unsubstituted carbon atoms, heterocycloalkyl groups with 2 to 20 substituted or unsubstituted carbon atoms, aralkyl groups with 6 to 30 substituted or unsubstituted carbon atoms, alkenyl groups with 2 to 20 substituted or unsubstituted carbon atoms, cycloalkenyl groups with 3 to 20 substituted or unsubstituted carbon atoms, and heteroalkenyl groups with 2 to 20 substituted or unsubstituted carbon atoms.

[0065] R1 to R4 may be the same or different, and are independently selected from hydrogen, deuterium, cyano, nitro, halogen, hydroxyl, substituted or unsubstituted alkylthio group with 1 to 4 carbon atoms, substituted or unsubstituted alkyl group with 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group with 3 to 20 carbon atoms, substituted or unsubstituted alkenyl group with 2 to 30 carbon atoms, substituted or unsubstituted alkynyl group with 2 to 24 carbon atoms, substituted or unsubstituted aralkyl group with 7 to 30 carbon atoms, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group with 1 to 60 carbon atoms, etc. The group consisting of heteroaryl groups having 2 to 30 substituted or unsubstituted carbon atoms, alkoxy groups having 1 to 30 substituted or unsubstituted carbon atoms, alkylamino groups having 1 to 30 substituted or unsubstituted carbon atoms, arylamino groups having 6 to 30 substituted or unsubstituted carbon atoms, arylalkylamino groups having 7 to 30 substituted or unsubstituted carbon atoms, heteroarylamino groups having 1 to 24 substituted or unsubstituted carbon atoms, alkylsilyl groups having 1 to 30 substituted or unsubstituted carbon atoms, arylsilyl groups having 6 to 30 substituted or unsubstituted carbon atoms, and aryloxy groups having 6 to 30 substituted or unsubstituted carbon atoms.

[0066] Embodiments of the present invention

[0067] The embodiments of the present invention are described in detail below to enable those skilled in the art to easily implement the invention. However, the present invention can be implemented through various different methods and is not limited to the embodiments described herein.

[0068] The novel organic compound of the present invention has relatively excellent interfacial properties with adjacent layers and can have excellent chemical stability. In particular, it has the highest occupied molecular orbital (HOMO) energy level that makes hole transport easy and has excellent hole transport characteristics for the light-emitting layer. Therefore, it can be used as a hole transport auxiliary layer material for organic electroluminescent devices.

[0069] Specifically, the compounds of the present invention are represented by the following chemical formula 1:

[0070] Chemical Formula 1

[0071]

[0072] Where n is an integer from 0 to 8,

[0073] m and q may be the same or different, and each is an independent integer from 0 to 4.

[0074] p is an integer from 0 to 2.

[0075] X is O or S.

[0076] L1 to L3 may be the same or different, and are independently selected from the group consisting of single bonds, aryl groups with 6 to 30 substituted or unsubstituted carbon atoms, heteroaryl groups with 1 to 30 substituted or unsubstituted carbon atoms, alkyl groups with 1 to 10 substituted or unsubstituted carbon atoms, cycloalkyl groups with 3 to 10 substituted or unsubstituted carbon atoms, alkenyl groups with 2 to 10 substituted or unsubstituted carbon atoms, cycloalkenyl groups with 3 to 10 substituted or unsubstituted carbon atoms, heteroalkyl groups with 1 to 10 substituted or unsubstituted carbon atoms, heterocycloalkyl groups with 2 to 10 substituted or unsubstituted carbon atoms, heteroalkenyl groups with 2 to 10 substituted or unsubstituted carbon atoms, and heterocycloalkenyl groups with 2 to 10 substituted or unsubstituted carbon atoms.

[0077] Ar1 and Ar2 may be the same or different, and are independently selected from the group consisting of aryl groups with 6 to 30 substituted or unsubstituted carbon atoms, heteroaryl groups with 1 to 30 substituted or unsubstituted carbon atoms, alkyl groups with 1 to 20 substituted or unsubstituted carbon atoms, cycloalkyl groups with 3 to 20 substituted or unsubstituted carbon atoms, heteroalkyl groups with 1 to 20 substituted or unsubstituted carbon atoms, heterocycloalkyl groups with 2 to 20 substituted or unsubstituted carbon atoms, aralkyl groups with 6 to 30 substituted or unsubstituted carbon atoms, alkenyl groups with 2 to 20 substituted or unsubstituted carbon atoms, cycloalkenyl groups with 3 to 20 substituted or unsubstituted carbon atoms, and heteroalkenyl groups with 2 to 20 substituted or unsubstituted carbon atoms.

[0078] R1 to R4 may be the same or different, and are independently selected from hydrogen, deuterium, cyano, nitro, halogen, hydroxyl, substituted or unsubstituted alkylthio group with 1 to 4 carbon atoms, substituted or unsubstituted alkyl group with 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group with 3 to 20 carbon atoms, substituted or unsubstituted alkenyl group with 2 to 30 carbon atoms, substituted or unsubstituted alkynyl group with 2 to 24 carbon atoms, substituted or unsubstituted aralkyl group with 7 to 30 carbon atoms, substituted or unsubstituted aryl group with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group with 1 to 60 carbon atoms, etc. The group consisting of heteroaryl groups having 2 to 30 substituted or unsubstituted carbon atoms, alkoxy groups having 1 to 30 substituted or unsubstituted carbon atoms, alkylamino groups having 1 to 30 substituted or unsubstituted carbon atoms, arylamino groups having 6 to 30 substituted or unsubstituted carbon atoms, arylalkylamino groups having 7 to 30 substituted or unsubstituted carbon atoms, heteroarylamino groups having 1 to 24 substituted or unsubstituted carbon atoms, alkylsilyl groups having 1 to 30 substituted or unsubstituted carbon atoms, arylsilyl groups having 6 to 30 substituted or unsubstituted carbon atoms, and aryloxy groups having 6 to 30 substituted or unsubstituted carbon atoms.

[0079] The compounds represented by the above chemical formula 1 can be represented by the following chemical formulas 2 to 4:

[0080] Chemical formula 2

[0081]

[0082] Chemical formula 3

[0083]

[0084] Chemical Formula 4

[0085]

[0086] Wherein, n, m, p, q, X, L1 to L3, Ar1, Ar2 and R1 to R4 are as defined in the above chemical formula 1.

[0087] The compounds represented by chemical formula 2 above can be represented by the following chemical formulas 5 to 7:

[0088] Chemical formula 5

[0089]

[0090] Chemical Formula 6

[0091]

[0092] Chemical Formula 7

[0093]

[0094] Wherein, n, m, p, q, X, L1 to L3, Ar1, Ar2 and R1 to R4 are as defined in the above chemical formula 1.

[0095] The compounds represented by the above chemical formula 3 can be represented by the following chemical formulas 8 to 10:

[0096] Chemical Formula 8

[0097]

[0098] Chemical formula 9

[0099]

[0100] Chemical Formula 10

[0101]

[0102] Wherein, n, m, p, q, X, L1 to L3, Ar1, Ar2 and R1 to R4 are as defined in the above chemical formula 1.

[0103] The compounds represented by the above chemical formula 4 can be represented by the following chemical formulas 11 to 13:

[0104] Chemical Formula 11

[0105]

[0106] Chemical formula 12

[0107]

[0108] Chemical formula 13

[0109]

[0110] Wherein, n, m, p, q, X, L1 to L3, Ar1, Ar2 and R1 to R4 are as defined in the above chemical formula 1.

[0111] The L1 to L3 mentioned above may be the same or different, and can be independently selected from the group consisting of arylene groups with 6 to 30 single bonds, substituted or unsubstituted carbon atoms, and heteroarylene groups with 1 to 30 substituted or unsubstituted carbon atoms.

[0112] The Ar1 and Ar2 mentioned above may be the same or different, and can be independently selected from the groups consisting of the following chemical formulas 14 to 17:

[0113] Chemical formula 14

[0114]

[0115] Chemical Formula 15

[0116]

[0117] Chemical Formula 16

[0118]

[0119] Chemical Formula 17

[0120]

[0121] In this context, * represents the bonding portion.

[0122] r is an integer from 0 to 5.

[0123] s and v may be the same or different, and each is an independent integer from 0 to 7.

[0124] t is an integer from 0 to 4.

[0125] u is an integer from 0 to 6.

[0126] Z is C(R) 10 (R) 11 ), N(R 12 ), O or S,

[0127] R5 to R 12The same or different, and independently selected from hydrogen, deuterium, cyano, nitro, halogen, hydroxyl, substituted or unsubstituted alkylthio group having 1 to 4 carbon atoms, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 24 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group having 1 to 60 carbon atoms, substituted or unsubstituted The group consisting of heteroaryl groups having 2 to 30 substituted carbon atoms, alkoxy groups having 1 to 30 substituted or unsubstituted carbon atoms, alkylamino groups having 1 to 30 substituted or unsubstituted carbon atoms, arylamino groups having 6 to 30 substituted or unsubstituted carbon atoms, arylalkylamino groups having 7 to 30 substituted or unsubstituted carbon atoms, heteroarylamino groups having 1 to 24 substituted or unsubstituted carbon atoms, alkylsilyl groups having 1 to 30 substituted or unsubstituted carbon atoms, arylsilyl groups having 6 to 30 substituted or unsubstituted carbon atoms, and aryloxy groups having 6 to 30 substituted or unsubstituted carbon atoms.

[0128] The Ar1 and Ar2 mentioned above may be the same or different, and are independently selected from the group consisting of substituted or unsubstituted phenylene, substituted or unsubstituted biphenylene, substituted or unsubstituted terphenylene, substituted or unsubstituted naphthyl, substituted or unsubstituted phenanthyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted spirofluorenyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothiophenyl, substituted or unsubstituted furanyl, and substituted or unsubstituted carbazoleyl.

[0129] The compounds represented by Chemical Formula 1 in this invention may be selected from, but are not limited to, the group consisting of:

[0130]

[0131]

[0132]

[0133]

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152]

[0153]

[0154]

[0155]

[0156]

[0157]

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168]

[0169]

[0170]

[0171]

[0172]

[0173]

[0174]

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181]

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191] The compound represented by the above chemical formula 1 can be effectively used as a hole transport auxiliary layer material.

[0192] According to one embodiment of the present invention, the compound of the above chemical formula 1 is bonded to an amino group on one side centered on dibenzofuran or dibenzothiophene, and to a carbazole group substituted with an aryl group on the other side. When used as a material for organic electroluminescent devices, it can exhibit luminous efficiency, lifetime and other properties that are equivalent to or better than most device characteristics.

[0193] According to another embodiment of the present invention, the compound of the above-mentioned chemical formula 1 is bonded to an amino group at one of the three positions of dibenzofuran or dibenzothiophene, and to a carbazole group substituted with an aryl group at the fourth position of dibenzofuran or dibenzothiophene on the other side. When used as a material for organic electroluminescent devices, it can exhibit luminous efficiency, lifetime and other characteristics that are equivalent to or better than most device characteristics.

[0194] The carbon positions of the above-mentioned dibenzofuran or dibenzothiophene are shown below.

[0195]

[0196] The organic electroluminescent device provided by the present invention comprises a compound represented by the above chemical formula 1.

[0197] The organic compounds of this invention can be effectively used as hole transport auxiliary layer materials.

[0198] Furthermore, the organic electroluminescent device of the present invention has a stacked organic thin film layer, which is a single-layer or multi-layer structure including a light-emitting layer, wherein the light-emitting layer is located between the cathode and the anode, and the organic thin film layer refers to a hole transport auxiliary layer located between the first electrode and the light-emitting layer.

[0199] The aforementioned hole transport auxiliary layer may contain a compound represented by the aforementioned chemical formula 1.

[0200] The aforementioned hole transport assist layer modulates hole injection characteristics by reducing the difference in highest occupied molecular orbital (HOMO) energy levels between the hole transport layer and the emissive layer. By reducing hole accumulation at the interface between the hole transport assist layer and the emissive layer, exciton quenching can be reduced through exciton elimination via polarons at the interface. Therefore, device stability and improved efficiency and lifetime can be achieved by reducing device thermalization.

[0201] The aforementioned organic electroluminescent device may have a structure consisting of an anode, a hole injection layer, a hole transport layer, a hole transport auxiliary layer, a light-emitting layer, an electron transport layer, an electron injection layer, and a cathode stacked together, and may also have an additional electron transport auxiliary layer stacked as needed.

[0202] The organic electroluminescent device of the present invention will be described below with reference to examples. However, the following examples do not limit the organic electroluminescent device of the present invention.

[0203] The organic electroluminescent device of the present invention may have a structure in which an anode (hole injection electrode), a hole injection layer (HIL), a hole transport layer (HTL), a hole transport auxiliary layer, an emissive layer (EML), and a cathode (electron injection electrode) are stacked sequentially. Preferably, a hole transport auxiliary layer is included between the anode and the emissive layer. Furthermore, an electron transport layer (ETL) and an electron injection layer (EIL) may be additionally included between the cathode and the emissive layer. Alternatively, an electron transport auxiliary layer may be included between the cathode and the emissive layer.

[0204] The following describes the fabrication method of the organic electroluminescent device of the present invention. First, an anode is formed by coating an anode material onto the surface of a substrate using conventional methods. In this case, the substrate used is preferably a glass substrate or a transparent plastic substrate that has excellent transparency, surface smoothness, ease of handling, and water resistance. Furthermore, transparent and highly conductive materials such as indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), and zinc oxide (ZnO) can be used as the anode material.

[0205] Next, a hole injection layer (HIL) is formed on the anode surface by vacuum thermal evaporation or spin-coating using conventional methods. For example, copper phthalocyanine (CuPc), 4,4',4”-tris(3-methylphenylamino)triphenylamine (m-MTDATA), 4,4',4”-tris(3-methylphenylamino)phenoxybenzene (m-MTDAPB), starburst amines such as 4,4',4”-tris(N-carbazolyl)triphenylamine (TCTA), 4,4',4”-tris(N-(2-naphthyl)-N-phenylamino)-triphenylamine (2-TNATA), or IDE406, which can be purchased from Idemitsu Corporation of Japan, are used as such hole injection layer materials.

[0206] A hole transport layer is formed by vacuum thermal evaporation or spin coating of a hole transport layer material onto the surface of the aforementioned hole injection layer using conventional methods. Commonly used hole transport layer materials can also be used as the aforementioned hole transport layer material.

[0207] The hole transport auxiliary layer can be formed by vacuum thermal evaporation or spin coating of the compound represented by the above chemical formula 1 on the surface of the hole transport layer. As described above, the hole transport auxiliary layer can use the compound of the present invention as the hole transport auxiliary layer material, and the hole transport auxiliary layer can be formed using commonly used hole transport auxiliary layer materials.

[0208] A light-emitting layer is formed by vacuum thermal evaporation or spin-coating of a light-emitting layer (EML) material onto the surface of the aforementioned hole transport auxiliary layer using conventional methods. In this case, when the single light-emitting material or the main light-emitting material is green, tris(8-hydroxyquinoline)aluminum (Alq3) can be used; for blue light, tris(8-hydroxyquinoline)aluminum (Alq3), 4,4'-N,N'-dicabazole-biphenyl (CBP), poly(n-vinylcabazole) (PVK), and 9,10-di(naphthalene-2-yl)anthracene (AND) can be used. 4,4',4”-tris(N-carbazolyl)triphenylamine (TCTA), 1,3,5-tris(N-phenylbenzimidazole-2-yl)benzene (TPBI), 3-tert-butyl-9,10-di(naphth-2-yl)anthracene (TBADN), estriol (E3), distyrylarylene (DSA), or mixtures of two or more thereof, but not limited thereto.

[0209] In the luminescent layer material, dopants that can be used together with the luminescent host include IDE102 and IDE105, which can be purchased from Idemitsu Corporation of Japan. Tris(2-phenylpyridine)iridium(III) (Ir(ppy)3), bis[(4,6-difluorophenyl)pyridyl-N,C-2']pyridinecarboxylic acid iridium(III) (FIrpic) (see reference [Chihaya Adachi et al., Appl. Phys. Lett., 2001, 79, 3082-3084]), octaethylporphyrin platinum(II) (PtOEP), TBE002 (Corbian Corporation), etc.

[0210] An electron transport layer is formed on the surface of the light-emitting layer by vacuum thermal evaporation or spin coating using conventional methods. There are no particular limitations on the electron transport layer material used; preferably, tris(8-hydroxyquinoline)aluminum (Alq3) can be used.

[0211] Selectively, a hole blocking layer (HBL) is further formed between the light-emitting layer and the electron transport layer, and a phosphorescent dopant is used in the light-emitting layer, thereby preventing triplet excitons or holes from diffusing into the electron transport layer.

[0212] The hole blocking layer can be formed by vacuum thermal evaporation or spin coating of the hole blocking layer material using conventional methods. There are no particular restrictions on the hole blocking layer material, but lithium (8-hydroxyquinoline) (Liq), bis(8-hydroxy-2-methylquinoline)-biphenoxyaluminum (BAlq), bath copper (BCP), and lithium fluoride (LiF) are preferred.

[0213] An electron injection layer is formed by vacuum thermal evaporation or spin-coating of an electron injection layer (EIL) material onto the surface of the aforementioned electron transport layer using conventional methods. In this case, materials such as LiF, Liq, Li₂O, BaO, NaCl, and CsF can be used for the electron injection layer.

[0214] The cathode is formed by vacuum thermal evaporation of a cathode material onto the surface of the electron injection layer using conventional methods.

[0215] In this case, the cathode material used can be lithium (Li), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium (Mg), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. Furthermore, the preceding light-emitting organic electroluminescent element can use indium tin oxide (ITO) or indium zinc oxide (IZO) to form a transparent cathode that allows light to pass through.

[0216] A capping layer (CPL) can be formed on the surface of the cathode using a capping layer forming composition.

[0217] The synthesis methods of the above-described compounds are described below with reference to representative examples. However, the synthesis methods of the compounds of the present invention are not limited to the methods illustrated below, and the compounds of the present invention can be prepared by the methods illustrated below and by methods known in the art.

[0218] Synthesis example

[0219] 1. Synthesis of SUB1

[0220] SUB1 can be synthesized in the following ways, but is not limited to these methods.

[0221] Reaction 1

[0222]

[0223] Under a nitrogen atmosphere, reactant 1 (89.64 mmol), reactant 2 (94.12 mmol), t-BuONa (179.28 mmol), Pd2(dba)3 (1.79 mmol), sphos (3.58 mmol), and toluene were added to a 500 mL flask and stirred under reflux. After the reaction was complete, the organic layer was extracted with toluene and water. The extracted organic layer was treated with MgSO4 to remove residual water, concentrated under reduced pressure, purified by column chromatography, and recrystallized to obtain SUB1.

[0224] Furthermore, the deuterium-substituted Ar1 and Ar2 can be synthesized in the same manner as in reaction formula 1 above. The synthesis results of SUB1 are shown in Table 1 below.

[0225] Table 1

[0226]

[0227]

[0228]

[0229]

[0230]

[0231] 2. Synthesis of SUB2

[0232] SUB2 can be synthesized via the following reaction formula 2, but is not limited to this. (X is O or S, Hal) 1 (Br, I or Cl)

[0233] Reaction 2

[0234]

[0235] Under a nitrogen atmosphere, reactant 3 (174.1 mmol), reactant 4 (182.8 mmol), K₂CO₃ (348.3 mmol), Pd(PPh₃)₄ (3.48 mmol), toluene, ethanol, and water were added to a 3000 mL flask and stirred under reflux. After the reaction was complete, the organic layer was extracted with toluene and water. The extracted organic layer was treated with MgSO₄ to remove residual water, concentrated under reduced pressure, purified by column chromatography, and recrystallized to obtain SUB₂.

[0236] Furthermore, deuterium-substituted reactants 3 and 4 can be synthesized in the same manner as in reaction formula 2 above. The synthesis results of SUB2 are shown in Table 2 below.

[0237] Table 2

[0238]

[0239]

[0240]

[0241]

[0242]

[0243] 3. Synthesis of compounds

[0244] The compound (product) can be synthesized in the following ways, but is not limited to these. (X is O or S, Hal) 1 (Br, I or Cl)

[0245]

[0246] Under a nitrogen atmosphere, SUB1 (16.33 mmol), SUB2 (15.56 mmol), t-BuONa (31.11 mmol), Pd2(dba)3 (0.31 mmol), sphos (0.622 mmol), and toluene were added to a 500 mL flask and stirred under reflux. After the reaction was complete, the organic layer was extracted with toluene and water. The extracted organic layer was treated with MgSO4 to remove residual water, concentrated under reduced pressure, purified by column chromatography, and recrystallized to obtain the compound. The synthesis results of the above compound (Product) are shown in Tables 3 to 20 below.

[0247] Table 3

[0248]

[0249]

[0250] Table 4

[0251]

[0252]

[0253] Table 5

[0254]

[0255]

[0256]

[0257] Table 6

[0258]

[0259]

[0260] Table 7

[0261]

[0262]

[0263] Table 8

[0264]

[0265]

[0266] Table 9

[0267]

[0268]

[0269]

[0270] Table 10

[0271]

[0272]

[0273]

[0274] Table 11

[0275]

[0276]

[0277] Table 12

[0278]

[0279]

[0280] Table 13

[0281]

[0282]

[0283] Table 14

[0284]

[0285]

[0286] Table 15

[0287]

[0288]

[0289]

[0290] Table 16

[0291]

[0292]

[0293]

[0294] Table 17

[0295]

[0296]

[0297] Table 18

[0298]

[0299]

[0300] Table 19

[0301]

[0302]

[0303]

[0304] Table 20

[0305]

[0306]

[0307] Example 1: Fabrication of an organic electroluminescent device (green)

[0308] On a substrate with a reflective layer, an anode is formed using indium tin oxide (ITO) and surface-treated with N2 plasma or UV-ozone. Next, a 10 nm thick HAT-CN layer is deposited on the anode to form a hole injection layer (HIL). Subsequently, a 110 nm thick N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine (N4,N4,N4',N4'-tetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine) layer is deposited on the hole injection layer to form a hole transport layer (HTL).

[0309] A hole transport auxiliary layer is formed by vacuum evaporating compound 1 with a thickness of 40 nm on the hole transport layer. At the same time, a light-emitting layer (EML) is formed by evaporating 35 nm of 4,4'-N,N'-dicarbazole-biphenyl (CBP) on the hole transport auxiliary layer, and approximately 5% by weight of [tris(2-phenylpyridine)-iridium] (Ir(ppy)3,3[tris(2-phenylpyridine)-iridium]) is doped into it as a dopant.

[0310] An electron transport layer (ETL) of 30 nm thickness was deposited on the light-emitting layer by mixing anthracene derivative and LiQ in a 1:1 ratio. An electron injection layer (EIL) of 1 nm thickness was then deposited on the ETL. Subsequently, a 16 nm thick mixture of magnesium (Mg) and silver (Ag) in a 1:4 ratio was deposited on the EIL to form a cathode. A 60 nm thick layer of N4,N4'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD) was deposited on the cathode to form a capping layer. Then, a sealcap containing a desiccant was attached to the capping layer using an UV-cured adhesive, thereby protecting the organic electroluminescent device from atmospheric O2 or moisture, thus fabricating the organic electroluminescent device.

[0311] Examples 2 to 252

[0312] Organic electroluminescent devices were prepared in the same manner as in Example 1, except that compounds 2 to 252 shown in Table 21 below were used instead of compound 1 in the hole transport auxiliary layer of Example 1.

[0313] Comparative Examples 1 to 3

[0314] Except that compounds A to C are used instead of compound 1 in the hole transport auxiliary layer of Example 1, the organic electroluminescent device is prepared in the same manner as in Example 1.

[0315]

[0316]

[0317] Experiment Example 1: Device Performance Analysis

[0318] The organic electroluminescent devices prepared in Examples 1 to 252 and Comparative Examples 1 to 3 were tested at 10 mA / cm². 2 Electro-optic characteristics under current driving and at 20mA / cm 2 The lifetime is reduced by 95% when driven by constant current, as shown in Table 21 below.

[0319] Table 21

[0320]

[0321]

[0322]

[0323]

[0324]

[0325]

[0326]

[0327] Example 253: Fabrication of an organic electroluminescent device (blue)

[0328] On a substrate with a reflective layer, an anode is formed using indium tin oxide (ITO) and surface-treated with N2 plasma or UV-ozone. Next, a 10 nm thick HAT-CN layer is deposited on the anode to form a hole injection layer (HIL). Subsequently, a 110 nm thick N4,N4,N4',N4'-tetratetra([1,1'-biphenyl]-4-yl)-[1,1'-biphenyl]-4,4'-diamine is deposited on the hole injection layer to form a hole transport layer (HTL).

[0329] A hole transport auxiliary layer is formed by vacuum evaporating compound 1 with a thickness of 15 nm on the hole transport layer. At the same time, a light-emitting layer (EML) is formed by evaporating 25 nm of 9,10-bis(2-naphthyl)anthracene (AND) on the hole transport auxiliary layer, and N1,N1,N6,N6-tetrakis(4-(1-methylsilyl)phenyl)pyrene-1,6-diamine is doped therein as a dopant at a weight percentage of about 3%.

[0330] An electron transport layer (ETL) of 30 nm thickness was deposited on the light-emitting layer by mixing anthracene derivative and LiQ in a 1:1 ratio. An electron injection layer (EIL) of 1 nm thickness was then deposited on the ETL. Subsequently, a 15 nm thick mixture of magnesium (Mg) and silver (Ag) in a 9:1 ratio was deposited on the EIL to form a cathode. A 60 nm thick layer of N4,N4'-bis[4-[bis(3-methylphenyl)amino]phenyl]-N4,N4'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (DNTPD) was then deposited on the cathode to form a capping layer. Finally, a sealcap containing a desiccant was attached to the capping layer using an UV-cured adhesive, thereby protecting the organic electroluminescent device from atmospheric O2 or moisture, thus fabricating the organic electroluminescent device.

[0331] Examples 254 to 511

[0332] Organic electroluminescent devices were prepared in the same manner as in Example 253, except that compounds 2 to 259 shown in Table 22 below were used instead of compound 1 in the hole transport auxiliary layer of Example 253.

[0333] Comparative Examples 4 to 6

[0334] Except that compounds A to C are used instead of compound 1 in the hole transport auxiliary layer of Example 253, the organic electroluminescent device is prepared in the same manner as in Example 253.

[0335]

[0336] Experiment Example 2: Device Performance Analysis

[0337] The organic electroluminescent devices prepared in Examples 253 to 511 and Comparative Examples 4 to 6 were tested at 10 mA / cm². 2 Electro-optic characteristics under current driving and at 20mA / cm 2The lifespan is reduced by 95% when driven by constant current, as shown in Table 22 below.

[0338] Table 22

[0339]

[0340]

[0341]

[0342]

[0343]

[0344]

[0345]

[0346]

[0347] Compounds 253 to 259 in Table 22 above are shown below.

[0348]

[0349] Based on the experimental results in Tables 21 and 22 above, compared with the comparative examples, when the compounds of the present invention are used as hole transport auxiliary layer materials for organic electroluminescent devices, it can be confirmed that they exhibit low driving voltage, excellent device efficiency characteristics, and long lifetime characteristics.

[0350] That is, the compounds in the comparative examples do not have dibenzofuran or dibenzothiophene bonded between the carbazole groups substituted with amino and aryl groups. As shown in the comparative example experimental results in Tables 21 and 22 above, the results of high driving voltage, reduced device efficiency and lifetime can be confirmed.

[0351] Furthermore, based on the experimental results in Tables 21 and 22 above, when the compounds of the present invention with partial or complete deuterium substitution are used as hole transport auxiliary layer materials for organic electroluminescent devices, it can be confirmed that the driving voltage is lower than that of the comparative examples, and they exhibit excellent device efficiency characteristics and long lifetime characteristics.

[0352] As described above, the embodiments disclosed in this specification do not limit the present invention. It is obvious that those skilled in the art can implement various modifications. Furthermore, even if the effects of the structures described in this invention are not explicitly stated, the effects predictable through the corresponding structures should be readily apparent.

[0353] Industrial applicability

[0354] This invention relates to organic compounds and organic electroluminescent devices containing the same.

Claims

1. A compound, characterized in that, The group consisting of compounds 69, 93, 98, 114, 121, 122, 123, 125, 126, 127, 153, 154, and 155 is selected. Compound 69: Compound 93: Compound 98: Compound 114: Compound 121: Compound 122: Compound 123: Compound 125: Compound 126: Compound 127: Compound 153: Compound 154: Compound 155: 。 2. An organic electroluminescent device, comprising: First electrode; The second electrode is arranged facing the first electrode described above; and One or more organic layers are disposed between the first electrode and the second electrode, and the organic electroluminescent device is characterized in that... At least one of the above-mentioned organic layers contains the compound according to claim 1.

3. The organic electroluminescent device according to claim 2, characterized in that, The aforementioned organic layer is selected from the group consisting of a hole injection layer, a hole transport layer, a hole transport auxiliary layer, a light-emitting layer, an electron transport layer, and an electron injection layer.

4. The organic electroluminescent device according to claim 2, characterized in that, The aforementioned organic layer serves as a hole transport auxiliary layer.

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