Composition for organic electroluminescent element and organic electroluminescent element containing the same

Abstract

The present invention relates to a composition for an organic EL element and an organic EL element containing the same. The composition for an organic EL element contains a first host represented by [Chemical Formula 1] and a second host represented by [Chemical Formula 2], and the above [Chemical Formula 1] and [Chemical Formula 2] are as defined in this specification.

Description

Technical Field

[0001] The present invention relates to a composition for an organic electroluminescence device and an organic electroluminescence device including the same.

Background Art

[0002] When a voltage is applied between two electrodes of an organic electroluminescence device (hereinafter abbreviated as "organic EL device"), holes are injected from the positive electrode and electrons are injected from the negative electrode into the organic layer. The injected holes and electrons meet to form excitons, and light is emitted when these excitons return to the ground state. At this time, the materials used as the organic layer are classified into a light-emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material, etc. according to their functions.

[0003] The light-emitting layer forming materials of organic EL devices can be classified into blue, green, and red light-emitting materials according to the emission color. Further, yellow and orange light-emitting materials may be used as light-emitting materials for realizing better natural colors. In addition, a host / dopant system is used as a light-emitting material for improving color purity and emission efficiency by energy transfer. The dopant substances are roughly classified into a fluorescent dopant using an organic substance and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. Since such phosphorescent materials can theoretically improve the emission efficiency by four times compared to fluorescence, not only phosphorescent dopants but also interest in phosphorescent host materials has been concentrated.

[0004] Currently, materials such as NPB, BCP, and Alq3 are widely known as materials used for the hole injection layer, hole transport layer, hole blocking layer, and electron transport layer, and anthracene derivatives have been reported as fluorescent dopant / host materials as the light-emitting material. In particular, among the light-emitting materials, metal complex compounds containing Ir such as Firpic, Ir(ppy)3, and (acac)Ir(btp)2 are used as dopant materials for blue, green, and red as phosphorescent materials that have significant advantages in terms of efficiency improvement. Currently, CBP exhibits excellent properties as a phosphorescent host material.

[0005] However, although conventional organic layer materials are advantageous in terms of light-emitting characteristics, they have a low glass transition temperature and poor thermal stability, so the lifetime in organic EL elements has been at an unsatisfactory level. Therefore, the development of organic layer materials with excellent performance is required.

Summary of the Invention

Problems to be Solved by the Invention

[0006] An object of the present invention is to provide a composition capable of realizing an organic EL element having high efficiency and long life.

[0007] Another object of the present invention is to provide an organic EL element having improved low driving voltage, high luminous efficiency, and long life characteristics by including the above composition as an organic layer material (for example, a light-emitting layer material).

Means for Solving the Problems

[0008] To achieve the above object, the present invention provides a composition for an organic EL element containing a first host represented by the following [Chemical Formula 1] and a second host represented by the following [Chemical Formula 2].

Chem.

Chem.

[0009] Further, the present invention provides an organic EL element including an anode; a cathode; and one or more organic layers interposed between the anode and the cathode, wherein the one or more organic layers contain the above-described composition.)

Advantages of the Invention

[0010] According to an embodiment of the present invention, by using in combination a compound having high hole characteristics and a compound having high electron characteristics as hosts, an organic EL element having low driving voltage, high efficiency, and long lifetime characteristics, and capable of exhibiting excellent phosphorescence generation characteristics can be realized.

[0011] The effects of the present invention are not limited by the content described above, and more various effects are included in this specification.

Brief Description of the Drawings

[0012]

Figure 1

Explanation of Reference Numerals

[0013] 100: Anode 200: Cathode 300: Organic layer 310: Hole transport region 311: Hole injection layer 312: Hole transport layer 320: Light emitting layer 330: Electron transport region 331: Electron transport layer 332: Electron injection layer

Modes for Carrying Out the Invention

[0014] Advantages, features, and methods for achieving them of the present invention will become apparent from the embodiments described in detail based on the accompanying drawings. However, the present invention is not limited to the embodiments disclosed below and can be implemented in various different forms, provided that the embodiments described below are for the purpose of a complete disclosure of the present invention and are provided so that those skilled in the art to which the present invention pertains can fully understand the scope of the invention, and the present invention should be defined by the scope of the claims. Therefore, in some embodiments, specific descriptions of well-known processes and steps, well-known element structures, and well-known technologies are omitted to avoid ambiguous interpretations of the present invention. The same reference numerals throughout this specification refer to the same components.

[0015] Unless otherwise defined, all terms (including technical and scientific terms) used in this specification have the meanings commonly understood by those of ordinary skill in the art to which the present invention pertains. Also, terms defined in commonly used dictionaries are not to be interpreted ideally or overly unless otherwise specified.

[0016] Also, throughout this specification, when a certain part "includes" a certain component, it means that, unless otherwise stated, it does not exclude other components but can further include other components. Note that throughout this specification, "above" or "on" means not only when located above or below the target part but also when there are other parts in between, and does not necessarily mean located above with reference to the direction of gravity.

[0017] Also, in this specification, terms such as "first" and "second" are not used to indicate any order or importance but are used to distinguish components.

[0018] <Composition for Organic EL Element> The composition for an organic EL element according to the present invention is a composition for forming an organic layer (for example, a light-emitting layer) of an organic EL element, and includes a first host represented by the above [Chemical Formula 1] and a second host represented by the above [Chemical Formula 2]. At this time, the first host is a compound having a structure in which three carbazoles are directly bonded without a linker, and is a P-type host having relatively high hole characteristics. The second host is a compound having a structure in which a dibenzo-based moiety is bonded to one phenyl moiety in a 2,4,6-triphenyl-N-containing heterocyclic moiety via a linker, and is an N-type host having relatively high electron characteristics. By using such a first host and a second host in combination, the composition according to the present invention can realize an organic EL element having high efficiency and long life.

[0019] In the first host represented by the above [Chemical Formula 1], a, d, and f are each an integer of 0 to 3, and b, c, and e are each an integer of 0 to 4. Here, when a, b, c, d, e, and f are each 0, it means that hydrogen is not substituted with deuterium (D). When a, d, and f are each an integer of 1 to 3, and b, c, and e are each an integer of 1 to 4, it means that one or more hydrogens are substituted with deuterium (D). At this time, 13 ≦ a + b + c + d + e + f ≦ 21 can be satisfied. As an example, the number of deuterium (D) atoms contained in the first host may be at least 13, specifically, at least 21. Such a first host can enhance the stability of the chemical structure by substitution with deuterium (D), and can simultaneously realize characteristics of the organic EL element, such as low voltage, high efficiency, and long life characteristics of the element.

[0020] Such deuterium may be substituted with other substituents (R). At this time, when there are a plurality of the other substituents (R), they may be the same as or different from each other. The other substituents (R) are a halogen group, a cyano group, a nitro group, an amino group, a C1-C 40 alkyl group, a C2-C 40 alkenyl group, a C2-C 40an alkynyl group, C3-C 40 a cycloalkyl group, a heterocycloalkyl group having 3 to 40 ring atoms, C6-C 60 an aryl group, a heteroaryl group having 5 to 60 ring atoms, C1-C 40 an alkyloxy group, C6-C 60 an aryloxy group, C1-C 40 an alkylsilyl group, C6-C 60 an arylsilyl group, C1-C 40 an alkylboron group, C6-C 60 an arylboron group, a phosphine oxide group, C1-C 40 an alkylphosphine oxide group, C6-C 60 an arylphosphine group, C6-C 60 an arylphosphine oxide group, and C6-C 60 may be selected from the group consisting of an arylamine group.

[0021] In the first host represented by the above [Chemical Formula 1], Ar1 and Ar2 are the same as or different from each other, and each independently is hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, C1-C 40 an alkyl group, C2-C 40 an alkenyl group, C2-C 40 an alkynyl group, C3-C 40 a cycloalkyl group, a heterocycloalkyl group having 3 to 40 ring atoms, C6-C 60 an aryl group, a heteroaryl group having 5 to 60 ring atoms, C1-C 40 an alkyloxy group, C6-C 60 an aryloxy group, C1-C 40 an alkylsilyl group, C6-C 60 an arylsilyl group, C1-C 40 an alkylboron group, C6-C 60 an arylboron group, a phosphine oxide group, C1-C 40 an alkylphosphine oxide group, C6-C 60 an arylphosphine group, C6-C 60 an arylphosphine oxide group, and C6-C 60selected from the group consisting of arylamine groups, or they may form a condensed ring with adjacent groups. Specifically, Ar1 and Ar2 are the same as or different from each other, and each independently may be selected from the group consisting of aryl groups having 6 to C 60 and heteroaryl groups having 5 to 60 nuclear atoms.

[0022] As an example, Ar1 and Ar2 may be the same as or different from each other, and each independently may be a substituent selected from the group consisting of the following substituents S1 to S4. [Chemical formula] In the above formula, * is the bonding site with the above [Chemical formula 1].

[0023] With such Ar1 and Ar2, the first host represented by the above [Chemical formula 1] may be a compound represented by the following [Chemical formula 3], but is not limited thereto. [Chemical formula] In the above formula, a, b, c, d, e, and f are as defined in the above [Chemical formula 1], m1 and m2 are each 0 or 1.

[0024] In addition, the first host represented by the above [Chemical formula 1] can have various structures depending on the bonding positions of the respective carbazole-based moieties. As an example, the first host represented by the above [Chemical formula 1] may be a compound represented by the following [Chemical formula 4]. [Chemical formula] In the above formula, a, b, c, d, e, and f are as defined in the above [Chemical formula 1], m1 and m2 are each 0 or 1.

[0025] Specifically, the first host represented by the above [Chemical Formula 1] can be a compound represented by the following [Chemical Formula 5].

Chem.

[0026] The first host represented by [Chemical Formula 1] according to the present invention as described above can be embodied in the following compounds, for example, Compounds A-1 to D-4, but is not limited to these examples.

Chem.

Chem.

[0027] In the second host represented by the above [Chemical Formula 2], Y1 and Y2 are the same as or different from each other, and each independently is N or C(Ar8), provided that at least one of Y1 and Y2 is N.

[0028] With such Y1 and Y2, in the second host represented by the above [Chemical Formula 2],

Chem.

Chem.

[0029] In the second host represented by the above [Chemical Formula 2], n1 is an integer from 1 to 5, and n2 is 0 or 1. As an example, n1 may be 1 or 2, and n2 may be 0 or 1. However, in the above [Chemical Formula 2], when n2 is 0, j is 1.

[0030] In the second host represented by the above [Chemical Formula 2], X1 is selected from the group consisting of O, S, Se, N(Ar3), C(Ar4)(Ar5), and Si(Ar6)(Ar7). With such X1, the dibenzo-based moiety can be a monovalent dibenzofuran group, a monovalent dibenzothiophene group, a monovalent fluorene group, etc.

[0031] Ar3 to Ar8 are the same as or different from each other, and each independently is hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a C1 to C 40 alkyl group, a C2 to C 40 alkenyl group, a C2 to C 40 alkynyl group, a C3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C1 to C 40 alkyloxy group, a C6 to C 60 aryloxy group, a C1 to C 40 alkylsilyl group, a C6 to C 60 arylsilyl group, a C1 to C 40 alkylboron group, a C6 to C 60 arylboron group, a phosphine oxide group, a C1 to C 40 alkylphosphine oxide group, a C6 to C 60 arylphosphine group, a C6 to C 60 arylphosphine oxide group, and a C6 to C 60Selected from the group consisting of arylamine groups, or these may form a condensed ring with adjacent groups (e.g., Ar3-R1, Ar3-R2, Ar4-Ar5, Ar6-Ar7, Ar4-R1, Ar4-R2, Ar6-R1, Ar6-R2, etc.). Specifically, Ar3 to Ar8 are the same as or different from each other, and each independently is a C1-C 40 alkyl group, a C6-C 60 aryl group, and a heteroaryl group having 5 to 60 nuclear atoms, or these may form a condensed ring with adjacent groups (e.g., Ar3-R1, Ar3-R2, Ar4-Ar5, Ar6-Ar7, Ar4-R1, Ar4-R2, Ar6-R1, Ar6-R2, etc.). Here, the above condensed ring is a C3-C 60 condensed aliphatic ring (specifically, a C3-C 30 condensed aliphatic ring), a C6-C 60 condensed aromatic ring (specifically, a C6-C 30 condensed aromatic ring), a 5- to 60-membered condensed heteroaromatic ring (specifically, a 5- to 30-membered condensed heteroaromatic ring), a C3-C 60 spiro ring, and one or more selected from the group consisting of combinations thereof.

[0032] As an example, in the above [Chemical Formula 2],

Chemical Structure

Chemical Structure

Chemical Structure

[0033] In the second host represented by the above [Chemical Formula 2], h is an integer from 0 to 3, g and i are each an integer from 0 to 4, and j and k are each an integer from 0 to 5. Here, when g, h, i, j, and k are each 0, it means that hydrogen is not substituted for R1 to R5 which are substituents. When h is an integer from 1 to 3, when g and i are each an integer from 1 to 4, and when j and k are each an integer from 1 to 5, one or more of R1 to R5 are the same as or different from each other, and each independently, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a C1 to C 40 alkyl group, a C2 to C 40 alkenyl group, a C2 to C 40 alkynyl group, a C3 to C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C6 to C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C1 to C 40 alkyloxy group, a C6 to C 60 aryloxy group, a C1 to C 40 alkylsilyl group, a C6 to C 60 arylsilyl group, a C1 to C 40 alkylboron group, a C6 to C 60 arylboron group, a phosphine oxide group, a C1 to C 40 alkylphosphine oxide group, a C6 to C 60 arylphosphine group, a C6 to C 60 arylphosphine oxide group, and a C6 to C 60 arylamine group, or these may form a condensed ring with adjacent groups. Specifically, one or more of R1 to R5 are the same as or different from each other, and each independently, hydrogen, a halogen group, a cyano group, a nitro group, an amino group, a C1 to C 40 alkyl group, a C6 to C 60 aryl group, and a heteroaryl group having 5 to 60 nuclear atoms, or may be selected from the group consisting of.

[0034] The alkyl groups, alkenyl groups, alkynyl groups, cycloalkyl groups, heterocycloalkyl groups, aryl groups, heteroaryl groups, alkyloxy groups, aryloxy groups, alkylsilyl groups, arylsilyl groups, alkylboron groups, arylboron groups, alkylphosphine oxide groups, arylphosphine groups, arylphosphine oxide groups, arylamine groups, and condensed rings of the above Ar3 to Ar8 and R1 to R5 are each independently deuterium, halogen, cyano group, nitro group, C2-C 40 alkenyl group of C2-C 40 alkynyl group of C2-C 40 cycloalkyl group of C3-C 40 alkyl group of C1-C 60 aryl group of C6-C 40 heteroaryl group having 5 to 60 ring atoms, alkyloxy group of C1-C 60 aryloxy group of C6-C 40 alkylsilyl group of C1-C 60 arylsilyl group of C6-C 40 alkylboron group of C1-C 60 arylboron group of C6-C 60 arylphosphine group of C6-C 60 arylphosphine oxide group of C6-C 60 and arylamine group of C6-C are substituted with one or more substituents selected from the group consisting of, or are unsubstituted. At this time, when there are a plurality of the above substituents, these may be the same as or different from each other.

[0035] The second host represented by the above [Chemical Formula 2] may be, but is not limited to, a compound represented by the following [Chemical Formula 6].

Chemical formula

[0036] Specifically, the second host represented by the above [Chemical Formula 2] may be a compound represented by the following [Chemical Formula 7] or [Chemical Formula 8], but is not limited thereto.

Chem.

Chem.

[0037] More specifically, the second host represented by the above [Chemical Formula 2] may be a compound represented by the following [Chemical Formula 9] or [Chemical Formula 10], but is not limited thereto.

Chem.

Chem.

[0038] The second host represented by the above [Chemical Formula 2] according to the present invention as described above can be embodied in the following compounds, for example, Compounds E-1 to E-13, but is not limited to these examples. [Chem.]

[0039] In the present invention, "alkyl" means a monovalent substituent derived from a linear or branched saturated hydrocarbon having 1 to 40 carbon atoms. Examples thereof include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl, etc.

[0040] In the present invention, "alkenyl" means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon double bonds. Examples thereof include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, etc.

[0041] In the present invention, "alkynyl" means a monovalent substituent derived from a linear or branched unsaturated hydrocarbon having 2 to 40 carbon atoms and having one or more carbon-carbon triple bonds. Examples thereof include, but are not limited to, ethynyl, 2-propynyl, etc.

[0042] In the present invention, "cycloalkyl" means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples thereof include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantyl, etc.

[0043] In the present invention, "heterocycloalkyl" means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 ring atoms, and one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with heteroatoms such as N, O, S or Se. Examples thereof include, but are not limited to, morpholine, piperazine, etc.

[0044] In the present invention, "aryl" means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, which is a single ring or a combination of two or more rings. Note that two or more rings may be in a pendant or fused form. Examples thereof include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, etc.

[0045] In the present invention, "heteroaryl" means a monovalent substituent derived from a monocyclic or polycyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At this time, one or more carbons in the ring, preferably 1 to 3 carbons, are substituted with heteroatoms such as N, O, S, or Se. Note that two or more rings may be in a pendant or fused form, and thus may be in a fused form with an aryl group. Examples thereof include, but are not limited to, 6-membered monocyclic rings such as pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, polycyclic rings such as phenoxathienyl, indolizinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl, and 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, etc.

[0046] In the present invention, "alkyloxy" means a monovalent substituent represented by R'O—, wherein R' means an alkyl having 1 to 40 carbon atoms. Such alkyloxy may have a linear, branched, or cyclic structure. Examples thereof include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy, etc.

[0047] In the present invention, "aryloxy" means a monovalent substituent represented by RO-, where R means aryl having 5 to 40 carbon atoms. Examples thereof include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, etc.

[0048] In the present invention, "alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, and includes not only mono-, but also di- and tri-alkylsilyl. Further, "arylsilyl" means silyl substituted with aryl having 5 to 60 carbon atoms, and includes not only mono-, but also polyarylsilyl such as di- and tri-arylsilyl.

[0049] In the present invention, "alkylboron" means boron substituted with alkyl having 1 to 40 carbon atoms, and "arylboron" means boron substituted with aryl having 6 to 60 carbon atoms.

[0050] In the present invention, "alkylphosphinyl group" means a phosphine group substituted with alkyl having 1 to 40 carbon atoms, and includes not only mono-, but also di-alkylphosphinyl group. Further, in the present invention, "arylphosphinyl group" means a phosphine group substituted with monoaryl or diaryl having 6 to 60 carbon atoms, and includes not only mono-, but also di-arylphosphinyl group.

[0051] In the present invention, "arylamine" means an amine substituted with aryl having 6 to 60 carbon atoms, and includes not only mono-, but also di-arylamine.

[0052] In the present invention, "heteroarylamine" means an amine substituted with heteroaryl having 5 to 60 nuclear atoms, and includes not only mono-, but also di-heteroarylamine.

[0053] In the present invention, "(aryl)(heteroaryl)amine" means an amine substituted with aryl having 6 to 60 carbon atoms and heteroaryl having 5 to 60 nuclear atoms.

[0054] In the present invention, the "condensed ring" means a condensed aliphatic ring having 3 to 40 carbon atoms, a condensed aromatic ring having 6 to 60 carbon atoms, a condensed heteroaliphatic ring having 3 to 60 nuclear atoms, a condensed heteroaromatic ring having 5 to 60 nuclear atoms, a spiro ring having 3 to 60 carbon atoms, or a combination thereof.

[0055] The content ratios of the above-described first host and second host may be a weight ratio of 99:1 to 1:99. Within such a range, bipolar characteristics can be more effectively realized, and efficiency and lifespan can be improved simultaneously.

[0056] The composition according to the present invention may further contain a phosphorescent dopant. The phosphorescent dopant is a substance that is mixed in trace amounts with the first and second hosts to cause luminescence, and is not particularly limited as long as it is known in the art. Examples include metal complex compounds containing iridium (Ir) or platinum (Pt), but are not limited thereto. Such dopants can cause luminescence by multiple excitation that excites a state of triplet or higher.

[0057] The above dopants are classified into red dopants, green dopants, and blue dopants, and can be used without particular limitation as long as they are ordinary red dopants, green dopants, and blue dopants known in the art.

[0058] Specifically, examples of red dopants include PtOEP (Pt(II) octaethylporphyrin), Ir(piq)3 (tris(2-phenylisoquinoline)iridium), Btp2Ir(acac) (bis(2-(2'-benzothienyl)-pyridinato-N,C3')iridium(acetylacetonate)), or a mixture of two or more thereof, but are not limited thereto.

[0059] In addition, examples of the green dopant include, but are not limited to, Ir(ppy)3 (tris-(2-phenylpyridine) iridium), Ir(ppy)2(acac) (bis(2-phenylpyridine)(acetylacetonate) iridium(III)), Ir(mppy)3 (tris(2-4-tolyl)phenylpyridine) iridium), or a mixture of two or more thereof.

[0060] Furthermore, examples of the blue dopant include, but are not limited to, F2Irpic (bis[3,5-difluoro-2-(2-pyridyl)phenyl](picolinato) iridium(III)), (F2ppy)2Ir(tmd), Ir(dfppz)3, or a mixture of two or more thereof.

[0061] The content of the dopant as described above is not particularly limited. For example, it is about 0 to 10% by weight, specifically about 0.1 to 10% by weight, and more specifically about 1 to 30% by weight based on the total weight of the above composition.

[0062] <Organic EL element> The organic EL element according to an embodiment of the present invention includes an anode; a cathode; and one or more organic layers interposed between the anode and the cathode, and the one or more organic layers include the above-described composition. As an example, the one or more organic layers include a light-emitting layer, and the above composition is included as a host material of the light-emitting layer. Thereby, the organic EL element of the present invention has low driving voltage, high efficiency, and long life characteristics, and can exhibit excellent phosphorescent emission characteristics.

[0063] Hereinafter, a preferred embodiment of the organic EL element according to the present invention will be described with reference to the accompanying drawings. However, the embodiments of the present invention can be variously modified and implemented, and the scope of the present invention is not limited to the embodiments described below. In order to avoid redundant description, the description of the components of the composition for an organic EL element described above will be omitted.

[0064] FIG. 1 is a cross-sectional view schematically showing the structure of an organic EL element according to an embodiment of the present invention.

[0065] As shown in FIG. 1, an organic EL element according to an embodiment of the present invention includes an anode 100 disposed on a substrate (not shown); a cathode 200 disposed opposite to the anode; and one or more organic layers 300 between the anode 100 and the cathode 200. The one or more organic layers 300 include a hole transport region 310, a light-emitting layer 320, and an electron transport region. At this time, the light-emitting layer 320 contains the above-described composition as a host. Optionally, the organic EL element according to the present invention may further include a capping layer (not shown) disposed on the cathode 200.

[0066] Hereinafter, each component of the organic EL element according to the present invention will be described in detail.

[0067] (1) Anode In the organic EL element of the present invention, the anode 100 is mainly disposed on the substrate, is electrically connected to the driving thin film transistor, and receives a driving current from the driving thin film transistor. Such an anode 100 is formed of a material having a relatively high work function, and thus serves to inject holes into the organic layer 300, that is, the hole transport region 310 (for example, the hole injection layer 311).

[0068] The material for forming such an anode is not particularly limited, and ordinary materials well known in the art can be used. For example, metals such as vanadium, chromium, copper, zinc, gold and their alloys; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al, SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, polyaniline; and carbon black, etc., but not limited thereto.

[0069] The method for manufacturing the above anode is not particularly limited and can be manufactured by a conventional method in the art. For example, it can be formed by coating the above anode material on a substrate by a well-known thin film formation method such as sputtering method, ion plating method, vacuum evaporation method, spin coating method, etc.

[0070] The above substrate is a plate-like member that supports the organic EL element, and examples include, but are not limited to, silicon wafers, quartz, glass plates, metal plates, plastic films, and sheets.

[0071] (2) Cathode In the organic EL element of the present invention, the cathode 200 is an electrode disposed opposite to the anode, and specifically, it is disposed on the electron transport region 330. Such a cathode 200 is formed of a material having a relatively low work function, and thus plays a role of injecting electrons into an adjacent organic layer, that is, into the electron transport region 330 (for example, the electron injection layer 332).

[0072] The material for forming such a cathode is not particularly limited, and ordinary materials well-known in the art can be used. For example, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver (Ag), tin, lead, and alloys thereof; and multilayer structured materials such as LiF / Al, LiO2 / Al, etc. are included, but not limited thereto.

[0073] The method for manufacturing the above cathode is not particularly limited, and like the anode, it can be manufactured by a conventional method in the art. For example, by the above-described thin film formation method, the above cathode material can be coated and formed on one or more of the following organic layers 300, specifically, on the electron transport region, for example, the electron injection layer 332.

[0074] (3) Organic layer In the organic EL element of the present invention, one or more organic layers 300 are disposed between the anode 100 and the cathode 200 and include a hole transport region 310, a light-emitting layer 320, and an electron transport region 330.

[0075] In one example, as shown in FIG. 1, one or more organic layers 300 include a hole injection layer 311, a hole transport layer 312, a light-emitting layer 320, an electron transport layer 331, and an electron injection layer 332 that are sequentially disposed on the anode 100.

[0076] Hereinafter, each organic layer will be described.

[0077] 1) Hole transport region In the organic EL element 100 of the present invention, the hole transport region 310 is a part of the organic layer 300 disposed on the anode 100 and serves to move holes injected from the anode 100 to the adjacent light-emitting layer 320.

[0078] Such a hole transport region 310 includes one or more selected from the group consisting of a hole injection layer 311 and a hole transport layer 312. At this time, in consideration of the characteristics of the organic EL element, it is preferable to include both the hole injection layer 31 and the hole transport layer 312. As an example, as shown in FIG. 1, the hole transport region 310 includes a hole injection layer 311 and a hole transport layer 312 that are sequentially stacked on the anode 100.

[0079] The materials for forming the hole injection layer 311 and the hole transport layer 312 are not particularly limited as long as they are substances with a low hole injection barrier and a high hole mobility, and the hole injection layer / transport layer materials used in the art can be used without limitation. Note that the materials for forming the hole injection layer 311 and the hole transport layer 312 may be the same as or different from each other.

[0080] Specifically, the above hole injection layer 311 comprises a hole injection material known in the art. Examples of the hole injection material include phthalocyanine compounds such as copper phthalocyanine; DNTPD (N,N'-diphenyl-N,N'-bis-[4-(phenyl-m-tolyl-amino)-phenyl]-biphenyl-4,4'-diamine), m-MTDATA (4,4',4''-tris(3-methylphenylphenylamino)triphenylamine), TDATA (4,4',4''-tris(N,N-diphenylamino)triphenylamine), 2TNATA (4,4',4''-tris{N,-(2-naphthyl)-N-phenylamino}-triphenylamine), PEDOT / PSS (poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate)), PANI / DBSA (polyaniline / dodecylbenzenesulfonic acid), PANI / CSA (polyaniline / camphorsulfonic acid), PANI / PSS (polyaniline) / poly(4-styrenesulfonate), etc., but are not limited thereto. These may be used alone or in combination of two or more.

[0081] The above hole transport layer 312 comprises a hole transport material known in the art. Examples of the hole transport material include carbazole derivatives such as N-phenylcarbazole and polyvinylcarbazole; fluorene derivatives; amine derivatives; triphenylamine derivatives such as TPD (N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1-biphenyl]-4,4'-diamine), TCTA (4,4'-4''-tris(N-carbazolyl)triphenylamine); NPB (N,N'-di(1-naphthyl)-N,N'-diphenylbenzidine), TAPC (4,4'-cyclohexylidenebis[N,N-bis(4-methylphenyl)benzenamine]), etc., but are not limited thereto. These may be used alone or in combination of two or more.

[0082] The above hole transport region 310 can be manufactured by conventional methods in the art. For example, vacuum evaporation method, spin coating method, casting method, LB (Langmuir - Blodgett) method, inkjet printing method, laser printing method, laser thermal transfer method (Laser Induced Thermal Imaging, LITI), etc. can be mentioned, but it is not limited thereto.

[0083] 2) Light - emitting layer In the organic EL element of the present invention, the light - emitting layer 320 is a part of the organic layer 300 interposed between the anode 100 and the cathode 200, and specifically, it is disposed on the above - mentioned hole transport region 320. As shown in FIG. 1, the light - emitting layer 320 may be disposed on the hole transport layer 312.

[0084] Such a light - emitting layer 320 is a layer in which holes and electrons injected from the anode and the cathode respectively combine to form excitons, and the color of the light emitted by the organic EL element changes depending on the material forming the light - emitting layer 320.

[0085] The light - emitting layer 320 according to the present invention includes a composition containing a first host represented by the above [Chemical formula 1] and a second host represented by the above [Chemical formula 2]. The above composition may selectively further contain a phosphorescent dopant. By including the above - described composition as the light - emitting layer 320 material, the organic EL element of the present invention has low driving voltage, high efficiency, and long - life characteristics, and can exhibit excellent phosphorescent emission characteristics.

[0086] The light - emitting layer 320 according to the present invention can be a red light - emitting layer containing a red phosphorescent material, a green light - emitting layer containing a green phosphorescent material, or a blue light - emitting layer containing a blue phosphorescent material. In one example, it may be a light - emitting layer containing a green phosphorescent material.

[0087] The above light-emitting layer 320 may include a single layer composed of one kind of substance, a single layer composed of a plurality of different substances, or a plurality of two or more layers composed of different materials. Here, when the light-emitting layer 320 is composed of a plurality of layers, the organic EL element can emit light of various colors. Specifically, the present invention can provide an organic EL element having a plurality of light-emitting layers made of different materials in series and presenting a mixed color. Further, when composed of a plurality of light-emitting layers, although the driving voltage of the element increases, the current value in the organic EL element becomes constant, and an organic EL element with improved luminous efficiency by the number of light-emitting layers can be provided.

[0088] Although not shown, the organic EL element of the present invention may include a plurality of light-emitting stacks (not shown) including at least one light-emitting layer.

[0089] The plurality of light-emitting layers included in such a light-emitting stack may be light-emitting layers that emit light of different colors from each other or light-emitting layers that emit light of the same color. That is, the emission color changes depending on the material constituting the light-emitting layer. As an example, the plurality of light-emitting stacks include substances that emit blue, green, red, yellow, white, etc., and are formed using phosphorescent or fluorescent substances. At this time, the colors indicated by each light-emitting layer may be in a complementary color relationship with each other. In addition, a color may be selected as a combination of colors that emit white. Each such light-emitting layer can include a phosphorescent dopant or a fluorescent dopant corresponding to the selected color, respectively.

[0090] Although not shown, the organic EL element of the present invention may further include a charge generation layer (Charge Generation Layer, CGL) (not shown) disposed between adjacent stacks among the plurality of light-emitting stacks and connecting them.

[0091] The charge generation layer (CGL) refers to a layer that does not directly contact two electrodes (for example, an anode and a cathode) and separates adjacent light-emitting stacks in an organic EL element including a plurality of light-emitting stacks. Such a charge generation layer is disposed between two adjacent light-emitting stacks, serves as a cathode that generates electrons and supplies electrons to one light-emitting stack, and serves as an anode that generates holes and supplies holes to the other light-emitting stack. As such a charge generation layer, a charge generation layer material known in the art can be used without limitation. Further, the material for the charge generation layer may be formed by doping a normal n-type substance and / or p-type substance known in the art.

[0092] The above light-emitting layer 320 can be manufactured by a conventional method in the art. For example, a vacuum evaporation method, a spin coating method, a casting method, an LB method, an inkjet printing method, a laser printing method, a laser thermal transfer method (LITI), etc. can be mentioned, but it is not limited thereto. As an example, the light-emitting layer can be formed by co-depositing a first host represented by the above [Chemical Formula 1] and a second host represented by the above [Chemical Formula 2]. At this time, the dopant may also be co-evaporated.

[0093] 3) Electron transport region In the organic EL element according to the present invention, the electron transport region 330 is an organic layer disposed on the light-emitting layer 320, and moves electrons injected from the cathode 200 to the light-emitting layer 320.

[0094] Such an electron transport region 330 includes one or more selected from the group consisting of an electron transport layer 331 and an electron injection layer 332.

[0095] As an example, as shown in FIG. 1, the electron transport region 330 includes an electron transport layer 331 and an electron injection layer 332 sequentially laminated on the light-emitting layer 320.

[0096] In the electron transport region 330 according to the present invention, the electron transport layer 331 can be used without particular limitation as long as it is an electron transport material that facilitates electron injection and has high electron mobility. Examples of such electron transport materials include oxazole-based compounds, isoxazole-based compounds, triazole-based compounds, isothiazole-based compounds, oxadiazole-based compounds, thiadiazole-based compounds, perylene-based compounds, aluminum complexes (e.g., Alq3 (tris(8-quinolinolato)-aluminum), BAlq, SAlq, Alph3, Almq3), gallium complexes (e.g., Gaq’2OPiv, Gaq’2OAc, 2(Gaq’2)), etc., but are not limited thereto. These may be used alone or in combination of two or more.

[0097] Further, the electron injection layer 332 can be used without particular limitation as long as it is an electron injection material that facilitates electron injection and has high electron mobility. Examples of the above electron injection materials include LiF, Li2O, BaO, NaCl, CsF; lanthanide metals such as Yb; or metal halides such as RbCl, RbI, etc., but are not limited thereto. These may be used alone or in combination of two or more.

[0098] As the electron transport region 330 according to the present invention, specifically, the electron transport layer 331 and / or the electron injection layer 332, those co-evaporated with an n-type dopant so that electrons can be easily injected from the cathode 200 may be used. At this time, as the n-type dopant, alkali metal complex compounds known in the art can be used without limitation, and examples include alkali metals, alkaline earth metals, or rare earth metals.

[0099] The above electron transport region 330 can be manufactured by conventional methods in the art. Examples include, but are not limited to, vacuum evaporation method, spin coating method, casting method, LB method, inkjet printing method, laser printing method, laser thermal transfer method (LITI), etc.

[0100] 4) Light-emitting auxiliary layer Although not shown, the organic EL element of the present invention may further include a light-emitting auxiliary layer disposed between the hole transport region 310 and the light-emitting layer 320.

[0101] The light-emitting auxiliary layer serves to transport holes from the hole transport region 310 to the light-emitting layer 320 or to adjust the thickness of the organic layer 300 by preventing the movement of electrons and / or excitons. In particular, since the light-emitting auxiliary layer has a high LUMO value, it prevents the movement of electrons to the hole transport layer 32, and since it has a high triplet energy, it prevents the diffusion of excitons in the light-emitting layer 320 to the hole transport layer 32.

[0102] Such a light-emitting auxiliary layer contains a hole transport material and may be manufactured from the same material as the hole transport region. Note that the light-emitting auxiliary layers of red, green, and blue organic light-emitting elements may be manufactured from the same material as each other.

[0103] The light-emitting auxiliary layer material is not particularly limited, and examples include carbazole derivatives and arylamine derivatives. Specifically, for example, NPD (N,N-dinaphthyl-N,N'-diphenylbenzidine), TPD (N,N'-bis(3-methylphenyl)-N,N'-bis(phenyl)-benzidine), s-TAD, MTDATA (4,4',4”-tris(N-3-methylphenyl-Nphenyl-amino)-triphenylamine), etc. are included, but are not limited thereto. These may be used alone or in combination of two or more.

[0104] In addition, the above light-emitting auxiliary layer may further contain a p-type dopant in addition to the materials described above. In the present invention, as the above p-type dopant, any p-type dopant known in the art can be used without particular limitation. At this time, the content of the p-type dopant can be appropriately adjusted within the range known in the art, and for example, it can be about 0.5 to 50 parts by weight with respect to 100 parts by weight of the hole transport material.

[0105] As is well known in the art, the above-mentioned light-emitting auxiliary layer can be formed by, but is not limited to, a vacuum evaporation method, a spin coating method, a casting method, an LB method, an inkjet printing method, a laser printing method, a laser thermal transfer method (LITI), etc.

[0106] 5) Hole blocking layer Although not shown in the drawings, the organic EL element 100 of the present invention may further include a hole blocking layer disposed between the light-emitting layer 320 and the electron transport region 330.

[0107] The above-mentioned hole blocking layer 333 can prevent excitons or holes generated in the light-emitting layer 320 from diffusing (moving) into the electron transport layer 331, and can improve the lifetime of the organic EL element.

[0108] As such a hole blocking layer material, any substance having normal electron transport characteristics known in the art can be used without particular limitation. Examples thereof include BCP (2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline), BAlq (bis(2-methyl-8-quinolinolato)(4-phenyl-phenolato)aluminum(III)), and the like.

[0109] As is well known in the art, the above-mentioned hole blocking layer can be formed by, but is not limited to, a vacuum evaporation method, a spin coating method, a casting method, an LB method, an inkjet printing method, a laser printing method, a laser thermal transfer method (LITI), etc.

[0110] (4) Capping layer Optionally, the organic EL element 100 of the present invention may further include a capping layer (not shown) disposed on the above-mentioned cathode 200.

[0111] The above-mentioned capping layer protects the organic EL element and plays a role in helping the light emitted from the organic layer to be efficiently emitted to the outside.

[0112] As the capping layer, at least one selected from the group consisting of tris-8-hydroxyquinoline aluminum (Alq3), ZnSe, 2,5-bis(6'-(2',2”-bipyridyl))-1,1-dimethyl-3,4-diphenylsilo, 4'-bis[N-(1-naphthyl)-N-phenyl-amino]biphenyl (α-NPD), N,N'-diphenyl-N,N'-bis(3-methylphenyl)-1,1'-biphenyl-4,4'-diamine (TPD), 1,1'-bis(di-4-tolylaminophenyl)cyclohexane (TAPC) can be used. The material for forming such a capping layer is less expensive than the material for forming other layers of the organic light-emitting device.

[0113] Such a capping layer may be a single layer, but may include two or more layers having different refractive indexes from each other, and the refractive index can be gradually changed while passing through the two or more layers.

[0114] The capping layer can be manufactured by conventional methods in the art, for example, by various methods such as vacuum evaporation method, spin coating method, casting method, or LB method.

[0115] The organic EL device according to the present invention as described above has a structure in which an anode 100, an organic layer 300, and a cathode 200 are sequentially laminated. If necessary, an insulating layer (not shown) or an adhesive layer (not shown) disposed between the anode 100 and the organic layer 300 or between the cathode 200 and the organic layer 300 may be further included. Such an organic EL device of the present invention has excellent lifetime characteristics because the half-life time (life time) of the initial luminance increases while maintaining the maximum luminous efficiency when voltage and current are applied.

[0116] The organic EL device of the present invention described above can be manufactured by a conventional method in the art. As an example, after vacuum-depositing an anode material on a substrate, materials for a hole transport region material, a light-emitting layer material, an electron transport region material, and a cathode material can be vacuum-deposited in order on the anode to manufacture an organic EL device.

Examples

[0117] Hereinafter, the present invention will be described in detail with reference to examples. However, the following examples are merely illustrative of the present invention, and the present invention is not limited by these examples.

[0118] <Preparation Example 1-1> Synthesis of Cz-D1

Chem.

[0119] After completion of the reaction, the mixture was extracted with ethyl acetate, then the water was removed with MgSO4, and purified by column chromatography (hexane:EA = 5:1 (v / v)) to obtain Cz-D1 (125.7 g, yield 72%). Mass (theoretical value: 329.25, measured value: 329 g / mol)

[0120] <Preparation Example 1-2> Synthesis of Cz-D2

Chem.

[0121] <Preparation Example 1-3> Synthesis of Cz-D3

Chem.

[0122] <Preparation Example 1-4>Synthesis of Cz-D4

Chemical formula

[0123] <Preparation Example 2-1>Synthesis of Cz-D5

Chemical formula

[0124] <Preparation Example 2-2>Synthesis of Cz-D6

Chemical formula

[0125] <Preparation Example 2-3> Synthesis of Cz-D7

Chemical formula

[0126] <Preparation Example 2-4> Synthesis of Cz-D8

Chemical formula

[0127] <Preparation Example 3-1> Synthesis of Cz-D9

Chemical formula

[0128] <Preparation Example 3-2> Synthesis of Cz-D10

Chemical formula

[0129] <Preparation Example 3-3> Synthesis of Cz-D11

Chemical formula

[0130] <Preparation Example 3-4> Synthesis of Cz-D12

Chemical formula

[0131] <Preparation Example 4-1> Synthesis of Cz-D13

Chemical formula

[0132] <Preparation Example 4-2>Synthesis of Cz-D14

Chemical formula

[0133] <Preparation Example 4-3>Synthesis of Cz-D15

Chemical formula

[0134] <Preparation Example 4-4>Synthesis of Cz-D16

Chemical formula

[0135] <Preparation Example 5-1> Synthesis of BCz-D1 <Step 1> Synthesis of 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-1,2,4,5,6,7,8-d7

Chemical formula

[0136] After completion of the reaction, the mixture was extracted with ethyl acetate, the water was removed with MgSO4, and the product was purified by column chromatography (hexane:EA = 8:1 (v / v)) to obtain 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-1,2,4,5,6,7,8-d7 (96.0 g, yield 84%). Mass (Theoretical value: 376.3, Measured value: 376 g / mol)

[0137] <Step 2> Synthesis of BCz-D1

Chemical formula

[0138] After completion of the reaction, the mixture was extracted with methylene chloride, filtered after adding MgSO4. Next, after removing the solvent from the obtained organic layer, it was purified by column chromatography (hexane:EA = 7:1 (v / v)) to obtain BCz-D1 (71.1 g, yield 66%). Mass (theoretical value: 422.59, measured value: 422 g / mol)

[0139] <Preparation Example 5-2> Synthesis of BCz-D2

Chemical formula

[0140] <Preparation Example 5-3> Synthesis of BCz-D3

Chemical formula

[0141] <Preparation Example 5-4> Synthesis of BCz-D4 [Chemical Formula] Except for using Cz-D4 (100 g, 246.7 mmol) obtained in Preparation Example 1-4 instead of Cz-D1 used in Preparation Example 5-1, the target compound BCz-D4 (59.4 g, final yield 48.3%) was obtained in the same manner as in Preparation Example 5-1. Mass (theoretical value: 498.69, measured value: 498 g / mol)

[0142] [Synthesis Example 1] Synthesis of A-1 [Chemical Formula] Under a nitrogen stream, BCz-D1 (10.0 g, 23.6 mmol) obtained in Preparation Example 5-1, Cz-D1 (9.3 g, 28.3 mmol) obtained in Preparation Example 1-1, Pd(OAc)2 (1.36 g, 1.18 mmol), P(t-Bu)3 (0.57 ml, 2.36 mmol), NaO(t-Bu) (4.55 g, 47.3 mmol), and toluene (100 ml) were mixed and stirred at 110 °C for 5 hours. After completion of the reaction, toluene was concentrated, the solid salt was filtered, and then purified by recrystallization to obtain the target compound A-1 (13.0 g, yield 82%). Mass (theoretical value: 670.93, measured value: 670 g / mol)

[0143] [Synthesis Example 2] Synthesis of A-2 [Chemical Formula] Except for using Cz-D2 (10.0 g, 23.6 mmol) obtained in Preparation Example 1-2 instead of Cz-D1 used in Synthesis Example 1, the target compound A-2 (13.8 g, yield 78%) was obtained in the same manner as in Synthesis Example 1. Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0144] [Synthesis Example 3] Synthesis of A-3 [Chemical formula] Compound A-3 (13.8 g, yield 75%) was obtained in the same manner as in Synthesis Example 1, except that Cz-D3 (10.0 g, 23.6 mmol) obtained in Preparation Examples 1-3 was used instead of Cz-D1 used in Synthesis Example 1. Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0145] [Synthesis Example 4] Synthesis of A-4 [Chemical formula] Compound A-4 (12.2 g, yield 69%) was obtained in the same manner as in Synthesis Example 1, except that Cz-D4 (10.0 g, 23.6 mmol) obtained in Preparation Examples 1-4 was used instead of Cz-D1 used in Synthesis Example 1. Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0146] [Synthesis Example 5] Synthesis of A-5 [Chemical formula] Compound A-5 (8.73 g, yield 55%) was obtained in the same manner as in Synthesis Example 1, except that Cz-D5 (9.3 g, 23.6 mmol) obtained in Preparation Example 2-1 was used instead of Cz-D1 used in Synthesis Example 1. Mass (theoretical value: 670.93, measured value: 670 g / mol)

[0147] [Synthesis Example 6] Synthesis of A-6 [Chemical formula] Compound A-6 (7.42 g, yield 42%) was obtained in the same manner as in Synthesis Example 1, except that Cz-D6 (10.0 g, 23.6 mmol) obtained in Preparation Example 2-2 was used instead of Cz-D1 used in Synthesis Example 1. Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0148] [Synthesis Example 7] Synthesis of A-7

Chem.

[0149] [Synthesis Example 8] Synthesis of A-8

Chem.

[0150] [Synthesis Example 9] Synthesis of A-9

Chem.

[0151] [Synthesis Example 10] Synthesis of A-10

Chem.

[0152] [Synthesis Example 11] Synthesis of A-11

Chemical Structure

[0153] [Synthesis Example 12] Synthesis of A-12

Chemical Structure

[0154] [Synthesis Example 13] Synthesis of A-13

Chemical Structure

[0155] [Synthesis Example 14] Synthesis of A-14

Chemical Structure

[0156] [Synthesis Example 15] Synthesis of A-15

Chemical formula

[0157] [Synthesis Example 16] Synthesis of A-16

Chemical formula

[0158] [Synthesis Example 17] Synthesis of B-1

Chemical formula

[0159] [Synthesis Example 18] Synthesis of B-2

Chemical formula

[0160] [Synthesis Example 19] Synthesis of B-3

Chemical formula

[0161] [Synthesis Example 20] Synthesis of B-4

Chemical formula

[0162] [Synthesis Example 21] Synthesis of C-1

Chemical formula

[0163] [Synthesis Example 22] Synthesis of C-2

Chemical formula

[0164] [Synthesis Example 23] Synthesis of C-3

Chemical formula

[0165] [Synthesis Example 24] Synthesis of C-4

Chemical formula

[0166] [Synthesis Example 25] Synthesis of D-1

Chemical formula

[0167] [Synthesis Example 26] Synthesis of D-2

Chemical formula

[0168] [Synthesis Example 27] Synthesis of D-3

Chemical formula

[0169] [Synthesis Example 28] Synthesis of D-4

Chemical formula

[0170] [Preparation Example 6] Synthesis of DBF-1 <Step 1> Synthesis of 4-(3-chlorophenyl)-6-phenyldibenzothiophene

Chemical formula

[0171] After completion of the reaction, the mixture was extracted with methylene chloride, and filtered after adding MgSO4. Next, after removing the solvent from the obtained organic layer, it was purified by column chromatography (hexane:DCM = 9:1 (v / v)) to obtain 4 - (3 - chlorophenyl) - 6 - phenyldibenzo[b,d]furan (48.9 g, yield 51%). Mass (theoretical value: 354.83, measured value: 354 g / mol)

[0172] <Step 2> Synthesis of DBF - 1

Chemical formula

[0173] After completion of the reaction, the mixture was extracted with ethyl acetate, the water was removed with MgSO4, and it was purified by column chromatography (hexane:DCM = 4:1 (v / v)) to obtain DBF - 1 (26.4 g, yield 43%). Mass (theoretical value: 446.35, measured value: 446 g / mol)

[0174] [Preparation Example 7] Synthesis of DBF-2 <Step 1> Synthesis of 4-(4-chlorophenyl)-6-phenyldibenzothiophene [Chemical Formula] Under a nitrogen stream, 4,4,5,5-tetramethyl-2-(6-phenyldibenzothiophene-4-yl)-1,3,2-dioxaborolane (100.0 g, 270.0 mmol), 1-bromo-4-chlorobenzene (62.0 g, 324.1 mmol), Pd(PPh3)4 (15.6 g, 13.5 mmol), K2CO3 (93.3 g, 675.2 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120 °C for 4 hours.

[0175] After completion of the reaction, extraction was performed with methylene chloride, and filtration was carried out after adding MgSO4. Next, after removing the solvent from the obtained organic layer, purification was performed by column chromatography (hexane:DCM = 9:1 (v / v)) to obtain 4-(4-chlorophenyl)-6-phenyldibenzothiophene (60.4 g, yield 63%). Mass (theoretical value: 354.83, measured value: 354 g / mol)

[0176] <Step 2> Synthesis of DBF-2 [Chemical Formula] Under a nitrogen stream, 4-(4-chlorophenyl)-6-phenyldibenzothiophene (60.4 g, 170.2 mmol) obtained in the above <Step 1>, 4,4,4’,4’,5,5,5’,5’-octamethyl-2,2’-bi(1,3,2-dioxaborolane) (47.5 g, 187.2 mmol), Pd(dppf)Cl2 (14.9 g, 17.0 mmol), KOAc (48.1 g, 510.4 mmol), and 1,4-dioxane (1000 ml) were mixed and stirred at 130 °C for 12 hours.

[0177] After completion of the reaction, the mixture was extracted with ethyl acetate, dried over MgSO4 to remove water, and purified by column chromatography (hexane:DCM = 4:1 (v / v)) to obtain DBF-2 (36.5 g, yield 48%). Mass (theoretical value: 446.35, measured value: 446 g / mol)

[0178] [Preparation Example 8] Synthesis of DBF-3 [Step 1] Synthesis of 3-(3-chlorophenyl)-6-phenyldibenzothiophene [Chemical formula] Under a nitrogen stream, 4,4,5,5-tetramethyl-2-(6-phenyldibenzothiophene-3-yl)-1,3,2-dioxaborolane (100.0 g, 270.0 mmol), 1-bromo-3-chlorobenzene (62.0 g, 324.1 mmol), Pd(PPh3)4 (15.6 g, 13.5 mmol), K2CO3 (93.3 g, 675.2 mmol), and 1,4-dioxane / H2O (1000 ml / 250 ml) were mixed and stirred at 120 °C for 4 hours.

[0179] After completion of the reaction, the mixture was extracted with methylene chloride, filtered after adding MgSO4. Next, the solvent was removed from the obtained organic layer and the residue was purified by column chromatography (hexane:DCM = 9:1 (v / v)) to obtain 3-(3-chlorophenyl)-6-phenyldibenzothiophene (68.0 g, yield 71%). Mass (theoretical value: 354.83, measured value: 354 g / mol)

[0180] [Step 2] Synthesis of DBF-3 [Chemical formula] Under a nitrogen stream, 3-(3-chlorophenyl)-6-phenyldibenzothiophene (68.0 g, 191.8 mmol) obtained in the above <Step 1>, 4,4,4’,4’,5,5,5’,5’-octamethyl-2,2’-bi(1,3,2-dioxaborolane) (53.6 g, 210.9 mmol), Pd(dppf)Cl2 (16.8 g, 19.2 mmol), KOAc (54.2 g, 575.3 mmol), and 1,4-dioxane (1000 ml) were mixed and stirred at 130 °C for 12 hours.

[0181] After completion of the reaction, the mixture was extracted with ethyl acetate, the water was removed with MgSO4, and the residue was purified by column chromatography (hexane:DCM = 4:1 (v / v)) to obtain DBF-3 (54.8 g, yield 64%). Mass (theoretical value: 446.35, measured value: 446 g / mol)

[0182] [Preparation Example 9] Synthesis of DBF-4 <Step 1> Synthesis of 1-(3-chlorophenyl)-6-phenyldibenzothiophene

Chemical formula

[0183] After completion of the reaction, the mixture was extracted with methylene chloride, filtered after adding MgSO4. Next, the solvent was removed from the obtained organic layer, and the residue was purified by column chromatography (hexane:DCM = 9:1 (v / v)) to obtain 1-(3-chlorophenyl)-6-phenyldibenzothiophene (62.3 g, yield 65%). Mass (theoretical value: 354.83, measured value: 354 g / mol)

[0184] <Step 2> Synthesis of DBF-4

Chemical formula

[0185] After completion of the reaction, the mixture was extracted with ethyl acetate, the moisture was removed with MgSO4, and purified by column chromatography (hexane:DCM = 4:1 (v / v)) to obtain DBF-4 (45.4 g, yield 58%). Mass (theoretical value: 446.35, measured value: 446 g / mol)

[0186] [Preparation Example 10] Synthesis of DBF-5 <Step 1> Synthesis of 1-(3-chlorophenyl)-9-phenyldibenzothiophene

Chemical formula

[0187] After completion of the reaction, the mixture was extracted with methylene chloride, and MgSO4 was added followed by filtration. Next, after removing the solvent from the obtained organic layer, it was purified by column chromatography (hexane:DCM = 9:1 (v / v)) to obtain 1-(3-chlorophenyl)-9-phenyldibenzothiophene (68.0 g, yield 71%). Mass (theoretical value: 354.83, measured value: 354 g / mol)

[0188] <Step 2> Synthesis of DBF-5

Chemical formula

[0189] After completion of the reaction, the mixture was extracted with ethyl acetate, and the water was removed with MgSO4, followed by purification by column chromatography (hexane:DCM = 4:1 (v / v)) to obtain DBF-5 (41.9 g, yield 49%). Mass (theoretical value: 446.35, measured value: 446 g / mol)

[0190] [Synthesis Example 29] Synthesis of E-1

Chemical formula

[0191] After completion of the reaction, extraction was performed with methylene chloride, and filtration was carried out after adding MgSO4. Next, after removing the solvent from the obtained organic layer, purification was performed by column chromatography (hexane:EA = 4:1 (v / v)) to obtain the target compound E-1 (11.8 g, yield 82%). Mass (theoretical value: 641.73, measured value: 641 g / mol)

[0192] [Synthesis Example 30] Synthesis of E-2

Chemical formula

[0193] [Synthesis Example 31] Synthesis of E-3

Chemical formula

[0194] [Synthesis Example 32] Synthesis of E-4

Chemical formula

[0195] [Synthesis Example 33] Synthesis of E-5

Chemical formula

[0196] [Synthesis Example 34] Synthesis of E-6

Chemical Structure

[0197] [Synthesis Example 35] Synthesis of E-7

Chemical Structure

[0198] [Synthesis Example 36] Synthesis of E-8

Chemical Structure

[0199] [Synthesis Example 37] Synthesis of E-9

Chemical formula

[0200] [Synthesis Example 38] Synthesis of E-10

Chemical formula

[0201] [Preparation Example 11] Synthesis of DBF-6 [Step 1] Synthesis of 4-(3'-chloro-[1,1'-biphenyl]-3-yl-2,2',4,4',5,5',6,6'-d8)-6-(phenyl-d5)dibenzo[b,d]furan-1,2,3,7,8,9-d6

Chemical formula

[0202] After completion of the reaction, the mixture was extracted with methylene chloride, and filtered after adding MgSO4. Next, after removing the solvent from the obtained organic layer, it was purified by column chromatography (hexane:DCM = 9:1 (v / v)) to obtain 4-(3'-chloro-[1,1'-biphenyl]-3-yl-2,2',4,4',5,5',6,6'-d8)-6-(phenyl-d5)dibenz[b,d]furan-1,2,3,7,8,9-d6 (83.8 g, yield 71%). Mass (theoretical value: 450.05, measured value: 450 g / mol)

[0203] <Step 2> Synthesis of DBF-6

Chemical formula

[0204] After completion of the reaction, the mixture was extracted with ethyl acetate, the water was removed with MgSO4, and it was purified by column chromatography (hexane:DCM = 4:1 (v / v)) to obtain DBF-6 (64.5 g, yield 64%). Mass (theoretical value: 541.57, measured value: 541 g / mol)

[0205] [Synthesis Example 39] Synthesis of E-11

Chemical formula

[0206] After completion of the reaction, extraction was carried out with methylene chloride, and filtration was performed after adding MgSO4. Next, after removing the solvent from the obtained organic layer, purification was carried out by column chromatography (hexane:EA = 4:1 (v / v)) to obtain the target compound E-11 (9.9 g, yield 73%). Mass (theoretical value: 736.94, measured value: 736 g / mol)

[0207] [Synthesis Example 40] Synthesis of E-12

Chemical formula

[0208] [Synthesis Example 41] Synthesis of E-13

Chemical formula

[0209] [Example 1] Fabrication of Green Organic EL Device Compound A-1 synthesized in Synthesis Example 1 and Compound E-1 synthesized in Synthesis Example 29 were purified by sublimation to high purity by a conventional method, and then a green organic EL device was fabricated according to the following procedure.

[0210] First, a glass substrate coated with a 1500 Å-thick ITO (Indium Tin Oxide) thin film was cleaned with ultrasonic distilled water. After the cleaning with distilled water was completed, ultrasonic cleaning was performed with solvents such as isopropyl alcohol, acetone, and methanol, dried, and then transferred to a UV ozone cleaner (Power sonic 405, manufactured by Facsinttec Co., Ltd.). Then, the above substrate was cleaned with UV for 5 minutes and transferred to a vacuum evaporator.

[0211] An organic EL device was fabricated by laminating 98 wt% of HT + 2 wt% of PA (100 Å) / HT (1200 Å) / HA (300 Å) / 60 wt% of Compound A-1 + 30 wt% of Compound E-1 + 10 wt% Ir(ppy)3 (400 Å) / EA (50 Å) / ET + LiQ (300 Å_1:1 molar ratio) / LiF (10 Å) / Al (1000 Å) in this order on the thus-prepared ITO transparent electrode.

[0212] The structures of HT, PA, HA, EA, ET, and Ir(ppy)3 used at this time are as follows. [Chemical formula]

[0213] [Examples 2 to 292] Fabrication of Green Organic EL Devices When forming the light-emitting layer in Example 1, among the light-emitting host materials, instead of using Compound A-1 used as Host 1, Compounds A-1 to D-4 described in Table 1 were each used, and instead of using Compound E-1 used as Host 2, Compounds E-2 to E-13 described in Table 1 were each used. A green organic EL device was fabricated in the same manner as in Example 1 except for this.

[0214] [Comparative Examples 1 to 12] Fabrication of Green Organic EL Devices When forming the light-emitting layer in the examples, among the light-emitting host materials, instead of using Compound A-1 used as Host 1, the following Compounds HT-1 to HT-4 were each used, and instead of using Compound E-1 used as Host 2, the following Compounds ET-1 to ET-7 were each used. A green organic EL device was fabricated in the same manner as in Example 1 except for this.

[0215] The structures of Compounds HT-1 to HT-4 and ET-1 to ET-7 used at this time are as follows. [Chemical formula]

[0216] [Evaluation Example 1] Regarding the green organic EL devices fabricated in Examples 1 to 292 and Comparative Examples 1 to 12, the driving voltage, current efficiency, emission peak, and lifetime at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 1 below.

[0217] [Table 1] JPEG2025520090000098.jpg240170JPEG2025520090000099.jpg243170JPEG2025520090000100.jpg241170JPEG2025520090000101.jpg241170JPEG2025520090000102.jpg241170JPEG2025520090000103.jpg229170

[0218] As shown in Table 1 above, the green organic EL devices obtained in Examples 1 to 292, which contain the compounds (A-1 to D-4) represented by [Chemical Formula 1] as the first host (P-type host) and the compounds (E-1 to E-13) represented by [Chemical Formula 2] as the second host (N-type host) according to the present invention, as host materials for the light-emitting layer, were found to have improved current efficiency, driving voltage, and lifetime characteristics compared to the green organic EL devices obtained in Comparative Examples 1 to 12 that used both the conventional host materials HT-1 to HT-4 and ET-1 to ET-7.

[0219] In addition, the green organic EL devices obtained in Examples 281 to 292, which contain the compounds (E-11 to E-13) in which deuterium is substituted as the second host (N-type host), were found to have superior current efficiency, driving voltage, and lifetime characteristics compared to the organic EL devices obtained in Examples 1 to 280 that contain the compounds (E-1 to E-10) in which deuterium is not substituted as the second host (N-type host). This is because the C-D bond, which has a higher bond dissociation energy than the C-H bond, is applied to the N-type host, which is an electron characteristic substance in the device, by the substitution of deuterium, thereby increasing the stability of the single molecule itself. In other words, it was confirmed that the compounds substituted with deuterium (for example, E-11 to E13) under the same structure can generate relatively more excitons than the compounds not substituted with deuterium (for example, E-1 to E-10), and the thermal denaturation due to the generation of excitons was reduced.

Claims

1. An organic EL device composition comprising a first host represented by the following [Chemical Formula 1] and a second host represented by the following [Chemical Formula 2]. 【Chemical 1】 【Chemical 2】 (In the formula, D is deuterium, a, d, f, and h are integers from 0 to 3, b, c, e, g, and i are each integers from 0 to 4, j and k are each integers from 0 to 5, n1 is an integer from 1 to 5, n2 is an integer of 0 or 1, X １ is selected from the group consisting of O, S, Se, N(Ar ３ ), C(Ar ４ )(Ar ５ ), and Si(Ar ６ )(Ar ７ ); Y １ and Y ２ are the same as or different from each other, and each independently is N or C(Ar ８ ), and at this time, Y １ and Y ２ at least one of them is N, Ar １ ~Ar ８ and R １ ~R ５ are the same as or different from each other, and each independently is hydrogen, deuterium (D), a halogen group, a cyano group, a nitro group, an amino group, a C １ ~C ４０ alkyl group, a C ２ ~C ４０ alkenyl group, a C ２ ~C ４０ alkynyl group, a C ３ ~C ４０ cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C ６ ~C ６０ aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C １ ~C ４０ alkyloxy group, a C ６ ~C ６０ aryloxy group, a C １ ~C ４０ alkylsilyl group, a C ６ ~C ６０ arylsilyl group, a C １ ~C ４０ alkylboron group, a C ６ ~C ６０ arylboron group, a phosphine oxide group, a C １ ~C ４０ alkylphosphine oxide group, a C ６ ~C ６０ arylphosphine group, a C ６ ~C ６０ arylphosphine oxide group, and a C ６ ~C ６０ arylamine group, or these may form a condensed ring with adjacent groups, The above Ar １ ~Ar ８ and R １ ~R ５ The alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkylboron group, arylboron group, alkylphosphine oxide group, arylphosphine group, arylphosphine oxide group, arylamine group, and condensed ring of are each independently deuterium, halogen, cyano group, nitro group, C ２ ~C ４０ The alkenyl group of, C ２ ~C ４０ The alkynyl group of, C ３ ~C ４０ The cycloalkyl group of, the heterocycloalkyl group having 3 to 40 nuclear atoms, C １ ~C ４０ The alkyl group of, C ６ ~C ６０ The aryl group of, the heteroaryl group having 5 to 60 nuclear atoms, C １ ~C ４０ The alkyloxy group of, C ６ ~C ６０ The aryloxy group of, C １ ~C ４０ The alkylsilyl group of, C ６ ~C ６０ The arylsilyl group of, C １ ~C ４０ The alkylboron group of, C ６ ~C ６０ The arylboron group of, C ６ ~C ６０ The arylphosphine group of, C ６ ~C ６０ The arylphosphine oxide group of, and C ６ ~C ６０ The arylamine group of is substituted with one or more substituents selected from the group consisting of, or is unsubstituted. When there are a plurality of these substituents, they may be the same as or different from each other. )

2. The organic EL device composition according to Claim 1, wherein the number of deuterium (D) atoms contained in the first host is at least 13.

3. The above Ar １ and Ar ２ are the same as or different from each other, and each independently is a substituent selected from the group consisting of the following substituents S1 to S4. The composition for an organic EL element according to claim 1. 【Chemical 3】

4. The organic EL device composition according to Claim 1, wherein the first host represented by the above [Chemical Formula 1] is a compound represented by the following [Chemical Formula 3]. 【Chemical Formula 4】 (In the formula, a, b, c, d, e, and f are as defined in Claim 1 respectively, m1 and m2 are each 0 or 1.)

5. The organic EL device composition according to Claim 1, wherein the first host represented by the above [Chemical Formula 1] is a compound represented by the following [Chemical Formula 4]. [Chemical Formula 5] (In the formula, a, b, c, d, e, and f are as defined in Claim 1 respectively, m1 and m2 are each 0 or 1.)

6. The organic EL device composition according to Claim 1, wherein the first host represented by the above [Chemical Formula 1] is a compound represented by the following [Chemical Formula 5]. [Chemical Formula 6] (In the formula, a, b, c, d, e, and f are as defined in Claim 1 respectively, m1 and m2 are each 0 or 1.)

7. The organic EL device composition according to Claim 1, wherein the first host represented by the above [Chemical Formula 1] is a compound selected from the group consisting of the following Compounds A-1 to D-4. 【Chemical Formula 7】 【Chemical 8】

8. In the second host represented by the above [Chemical Formula 2], 【Chemical Formula 9】 the moiety is a moiety selected from the group consisting of the following Moieties Mo-1 to Mo-3, the organic EL device composition according to Claim 1. 【Chemical 10】 (In the formula, * is the bonding site with the above [Chemical Formula 2], Y １ and Y ２ are each independently C(Ar ８ ) and Ar ８ is as defined in claim 1.)

9. In the above [Chemical Formula 2], 【Chemical 11】 the moiety is a moiety selected from the group consisting of the following Moieties Dz-1 to Dz-32, the organic EL device composition according to Claim 1. 【Chemical 12】 【Chemical 13】 (In the formula, R １ is an aryl group of C ６ to C ６０ .)

10. The organic EL device composition according to Claim 1, wherein the second host represented by the above [Chemical Formula 2] is a compound represented by the following [Chemical Formula 6]. 【Chemical 14】 (In the formula, i, j, k, R １ , R ３ ~R ５ , n1, n2, X １ , Y １ , and Y ２ are as defined in claim 1, respectively.)

11. The composition for an organic EL element according to claim 1, wherein the second host represented by the above [Chemical Formula 2] is a compound represented by the following [Chemical Formula 7] or [Chemical Formula 8]. 【Chemical Formula 15】 【Chemical 16】 (In the formula, i, k, R １ , R ３ , R ５ , n1, n2, Y １ , and Y ２ are as defined in claim 1, respectively, X １ and X ２ is each O or S.)

12. The composition for an organic EL element according to claim 1, wherein the second host represented by the above [Chemical Formula 2] is a compound represented by the following [Chemical Formula 9] or [Chemical Formula 10]. 【Chemical 17】 【Chemical 18】 (In the formula, n1, n2, Y １ and Y ２ are as defined in claim 1, respectively, x and y are each 0 or 1, X １ and X ２ is each O or S, D is deuterium, o1 is an integer from 0 to 5, o2 is an integer from 0 to 6, o3 is an integer from 0 to 4, o4 is an integer from 0 to 3, o5 is an integer from 0 to 7.)

13. The composition for an organic EL element according to claim 1, wherein the second host represented by the above [Chemical Formula 2] is selected from the group consisting of the following compounds E-1 to E-13. 【Chemical Formula 19】

14. The composition for an organic EL element according to claim 1, wherein the content ratio of the above first host and second host is a weight ratio of 99:1 to 1:

99.

15. The composition for an organic EL element according to claim 1, wherein the above composition further contains a phosphorescent dopant.

16. The composition for an organic EL element according to claim 15, wherein the above phosphorescent dopant contains iridium (Ir) or platinum (Pt).

17. An anode; a cathode; and one or more organic layers interposed between the above anode and cathode; are included, The organic EL element, wherein the one or more organic layers contain the composition according to any one of claims 1 to 16.

18. The one or more organic layers include a light-emitting layer, The organic EL element according to claim 17, wherein the above composition is contained in the above light-emitting layer.

Images