Pellet for organic electroluminescence element and organic electroluminescence element using the same

Abstract

The present invention relates to a pellet for an organic EL element and an organic EL element using the same. The pellet for an organic EL element is obtained by pressure-bonding two or more kinds of organic compound powders including a first organic compound powder and a second organic compound powder, and among the first organic compound and the second organic compound, has the same maximum emission wavelength as that of the organic compound having a longer emission wavelength.

Description

Technical Field

[0001] The present invention relates to a pellet for an organic electroluminescence element and an organic electroluminescence element using the same.

Background Art

[0002] When a voltage is applied between two electrodes of an organic electroluminescence element (hereinafter abbreviated as "organic EL element"), 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 organic substances used as the organic layer are classified into a light-emitting substance, a hole injection substance, a hole transport substance, an electron transport substance, an electron injection substance, etc. according to their functions.

[0003] In order to improve the performance of such an organic EL element, particularly the lifetime, efficiency, and driving voltage, many organic compounds, for example, one or more host materials in which a dopant is dispersed, are used to form the organic layer. The above organic layer is formed by evaporating a number of organic compounds respectively. At this time, it is difficult to accurately control each organic compound at a desired evaporation rate, and there is a relatively waste in terms of material utilization. Further, since the organic compound is in powder form, there is a problem that it is charged with static electricity and is difficult to handle during vapor deposition.

Summary of the Invention

Problems to be Solved by the Invention

[0004] An object of the present invention is to provide a pellet capable of realizing an organic EL element having excellent thermal stability and chemical stability, as well as low surface resistance, a small specific surface area, high efficiency, and a long lifetime.

Means for Solving the Problems

[0005] In order to achieve the above object, the present invention provides an organic EL element pellet in which two or more kinds of organic compound powders containing a first organic compound powder and a second organic compound powder are pressure-bonded, and among the first organic compound and the second organic compound, the organic compound having the same maximum emission wavelength as the maximum emission wavelength of the organic compound having a longer emission wavelength is provided.

[0006] The pellet according to the present invention has the same maximum emission wavelength as the maximum emission wavelength of the mixed powder of the first organic compound powder and the second organic compound powder.

[0007] The pellet according to the present invention includes a first region portion where the first organic compound powder is pressure-bonded, and a second region portion where the second organic compound powder is pressure-bonded and is arranged integrally with the first region portion.

[0008] In the pellet according to the present invention, the first region portion and the second region portion are alternately arranged in the circumferential direction from the center to the outer periphery.

[0009] In the pellet according to the present invention, the first region portion and the second region portion are arranged in the length direction. At this time, the first region portion and the second region portion may be alternately arranged.

[0010] In the pellet according to the present invention, the first region portion and the second region portion are alternately arranged in the circumferential direction. At this time, the first region portion and the second region portion may be alternately arranged vertically.

[0011] The pellet according to the present invention has a shape selected from the group consisting of a polyhedron, a cylinder, and a sphere.

[0012] In the pellet according to the present invention, the content ratio of the first organic compound powder and the second organic compound powder is a weight ratio of 1:99 to 99:1.

[0013] In the pellet according to the present invention, both the first organic compound powder and the second organic compound powder are sublimable powders.

[0014] In the pellet according to the present invention, the above first organic compound powder and the second organic compound powder have a vapor deposition temperature difference of 0 to 30°C under a pressure of 10 -6 torr.

[0015] In the pellet according to the present invention, the above first organic compound is a hole-transporting organic compound, and the above second organic compound is an electron-transporting organic compound. At this time, the above hole-transporting organic compound is a hole-transporting host, and the above hole-transporting host is a carbazole-based compound. The above electron-transporting organic compound is an electron-transporting host, and the above electron-transporting host is an azine-based compound.

[0016] The pellet according to the present invention is a molded body injection-molded under the condition of applying a pressure of 20,000 to 40,000 kgf / cm 2 without performing heat treatment on the above two or more kinds of organic compound powders.

[0017] The pellet according to the present invention has a BET specific surface area smaller than that of a simple mixture of the above first organic compound powder and the second organic compound powder.

[0018] The pellet according to the present invention has a surface resistance smaller than that of a simple mixture of the above first organic compound powder and the second organic compound powder.

[0019] The present invention provides an organic EL element including an anode; a cathode; and one or more organic layers interposed between the above anode and the cathode, wherein at least one of the one or more organic layers is a homogeneous thin film containing the above first organic compound and the second organic compound using the above-described pellet.

Advantages of the Invention

[0020] The pellets according to the present invention have excellent thermal and chemical stability, low surface resistance, a small specific surface area, good reproducibility of thin films, and excellent uniformity of thin films. Therefore, it is possible to realize an organic EL element having high efficiency and long life.

Brief Description of Drawings

[0021]

Figure 1

Figure 2

Figure 3

Figure 4

Explanation of Signs

[0022] 10: Pellet, 11: First region part, 12: Second region part, 13: Third region part, 100: Anode, 200: Cathode, 300: Organic layer, 310: Hole injection layer, 320: Hole transport layer, 330: Light emitting layer, 340: Electron transport layer, 350: Electron injection layer, 360: Electron transport auxiliary layer

Embodiments for Carrying Out the Invention

[0023] Hereinafter, the present invention will be described in detail.

[0024] Unless otherwise defined, all terms (including technical and scientific terms) used in this specification have the meaning commonly understood by those of ordinary skill in the technical field to which the present invention belongs. Also, terms defined in commonly used dictionaries are not to be construed in an idealized or overly interpreted manner unless otherwise noted.

[0025] Also, throughout this specification, when a part "includes" a certain component, it should be understood as an open-ended term meaning that, unless otherwise specified, it does not exclude other components but may further include other components.

[0026] In addition, throughout this specification, "above" or "on" does not necessarily mean located above with respect to the direction of gravity, and includes not only the case where it is located above or below the target part but also the case where there are other parts in between.

[0027] 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.

[0028] <Pellet for Organic EL Element> The present invention provides a pellet for forming an organic layer (for example, a light-emitting layer) of an organic EL element.

[0029] The pellet according to the present invention is a molded body in which two or more kinds of organic compound powders including a first organic compound powder and a second organic compound powder are pressure-bonded, and the maximum emission wavelength of the pellet is the same as that of the organic compound having a longer emission wavelength among the first organic compound and the second organic compound.

[0030] Specifically, the pellets of the present invention are formed by simply mixing the first organic compound powder and the second organic compound powder and then performing pressure molding without heat treatment, whereby the first organic compound powder and the second organic compound powder are densified without chemically changing. Thus, the pellets of the present invention are produced without the first organic compound powder and the second organic compound powder chemically changing. As a result, the maximum emission wavelength of the pellets of the present invention is the same as the maximum emission wavelength of the organic compound having the longer emission wavelength among the first organic compound and the second organic compound, and is also the same as the maximum emission wavelength of a simple mixture powder of the first organic compound powder and the second organic compound powder. Further, the pellets of the present invention have a BET specific surface area smaller than the BET specific surface area of a simple mixture of the first organic compound powder and the second organic compound powder. Therefore, the pellets of the present invention have a small exposed area to air, are excellent in chemical resistance, and are excellent in thermal stability. Also, the pellets according to the present invention have a surface resistance smaller than the surface resistance of a simple mixture of the first organic compound powder and the second organic compound powder, so that static electricity is less likely to be generated and their handling is easy, whereby the processability of the evaporation step can be improved during the manufacture of the device. Further, the pellets of the present invention are not only excellent in storage and handleability, but can be variously designed into desired shapes. Also, the pellets of the present invention can be used as a single evaporation source and the control of the evaporation rate is easy, so that the evaporation step can be simplified and the manufacturing cost can be reduced. Furthermore, when forming the organic layer of the organic EL device using the pellets of the present invention, compared with the case where the first organic compound powder and the second organic compound powder are used respectively or in a state of being simply mixed together, a thin film in which the first organic compound and the second organic compound are homogeneously mixed is formed, so that an organic EL device having high efficiency and long life can be realized. Also, the pellets of the present invention have good reproducibility of the thin film during the evaporation of the thin film by a continuous process, and it is possible to continuously manufacture the organic EL device by a continuous process such as a roll-to-roll process.

[0031] In the pellet of the present invention, both the first organic compound powder and the second organic compound powder are powders that are solid at room temperature and can sublime. Therefore, the pellet according to the present invention can easily form a homogeneous thin film by a dry film-forming method such as a vacuum evaporation method.

[0032] As an example, the first organic compound powder and the second organic compound powder can have a sublimation temperature difference of about 0 to 30 °C under a pressure of 10 -6 torr. Therefore, the first organic compound powder and the second organic compound powder may have a deposition temperature difference of about 0 to 30 °C under a pressure of 10 -6 torr. In this case, the pellet of the present invention can be deposited while maintaining the set mixing ratio.

[0033] The first organic compound that can be used in the present invention is not particularly limited as long as it is a compound having higher hole transport characteristics than the second organic compound, that is, a hole transporting organic compound.

[0034] The hole transporting organic compound can be a hole transporting host. As an example, the hole transporting host may be a carbazole-based compound.

[0035] Specifically, examples of the hole transporting organic compound include, but are not limited to, the compound represented by the following [Chemical Formula 1].

Chemical Formula

[0036] In the compound 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). On the other hand, when a, d, and f are each an integer of 1 to 3, and when 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 deuteriums (D) contained in the compound represented by the above [Chemical Formula 1] is at least 13, specifically at least 21. Such a compound represented by [Chemical Formula 1] can enhance the stability of the chemical structure by substitution with deuterium (D), and simultaneously realize characteristics of the organic EL element, such as low voltage, high efficiency, and long life characteristics of the element.

[0037] Such deuterium may be substituted with other substituents (R). At this time, when there are a plurality of other substituents (R), these may be the same as or different from each other. Examples of the above other substituents (R) include 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 40 alkynyl group, a C3-C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C6-C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C1-C 40 alkyloxy group, a C6-C 60 aryloxy group, a C1-C 40 alkylsilyl group, a C6-C 60 arylsilyl group, a C1-C 40 alkylboron group, a C6-C60 The aryl boron group, phosphine oxide group, C1-C 40 alkyl phosphine oxide group, C6-C 60 aryl phosphine group, C6-C 60 aryl phosphine oxide group, and C6-C 60 aryl amine group may be selected from the group consisting of.

[0038] In the compound 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), halogen group, cyano group, nitro group, amino group, C1-C 40 alkyl group, C2-C 40 alkenyl group, C2-C 40 alkynyl group, C3-C 40 cycloalkyl group, heterocycloalkyl group having 3 to 40 nuclear atoms, C6-C 60 aryl group, heteroaryl group having 5 to 60 nuclear atoms, C1-C 40 alkyloxy group, C6-C 60 aryloxy group, C1-C 40 alkylsilyl group, C6-C 60 arylsilyl group, C1-C 40 alkyl boron group, C6-C 60 aryl boron group, phosphine oxide group, C1-C 40 alkyl phosphine oxide group, C6-C 60 aryl phosphine group, C6-C 60 aryl phosphine oxide group, and C6-C 60 aryl amine group may be selected, or these 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 C6-C 60 aryl group, and heteroaryl group having 5 to 60 nuclear atoms.

[0039] As an example, the above Ar1 and Ar2 are 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 substituents S1 to S4, * is the bonding site with the above [Chemical formula 1].

[0040] With such Ar1 and Ar2, the compound represented by the above [Chemical formula 1] can be, but is not limited to, the compound represented by the following [Chemical formula 2].

[0041] [Chemical formula] In the above formula, a, b, c, d, e, and f are as defined in the above [Chemical formula 1], respectively, m1 and m2 are each 0 or 1.

[0042] Note that the compound represented by the above [Chemical formula 1] can have various structures depending on the bonding positions of each carbazole-based moiety. As an example, the compound represented by the above [Chemical formula 1] can be the compound represented by the following [Chemical formula 3]. [Chemical formula] In the above formula, a, b, c, d, e, and f are as defined in the above [Chemical formula 1], respectively, m1 and m2 are each 0 or 1.

[0043] The compound 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. [Chemical formula] [Chemical formula]

[0044] As the second organic compound that can be used in the present invention, there is no particular limitation as long as it is a compound having higher electron transport characteristics than the first organic compound, that is, an electron transporting organic compound.

[0045] The above electron transporting organic compound can be an electron transporting host. As an example, the above electron transporting host can be a pyrimidine compound containing a triazine group, a pyridine group, a pyrimidine group, or the like.

[0046] Specifically, examples of the above electron transporting organic compound include, but are not limited to, a compound represented by the following [Chemical Formula 4].

Chemical Formula

[0047] In the compound represented by the above [Chemical Formula 4], 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.

[0048] With such Y1 and Y2, in the compound represented by the above [Chemical Formula 4],

Chem.

Chem.

[0049] In the compound represented by the above [Chemical Formula 4], n1 is an integer from 1 to 5, and n2 is 0 or 1. As an example, n1 is 1 or 2, and n2 is 0 or 1. However, in the above [Chemical Formula 4], when n2 is 0, j is 1.

[0050] In the compound represented by the above [Chemical Formula 4], X1 may be selected from the group consisting of O, S, Se, N(Ar3), C(Ar4)(Ar5), and Si(Ar6)(Ar7). With such X1, examples of the dibenzo-based moiety include a monovalent dibenzofuran group, a monovalent dibenzothiophene group, and a monovalent fluorene group.

[0051] 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 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 40 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 an arylamine group, or are selected from the group consisting of, 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, C1-C 40 an alkyl group, C6-C 60 an aryl group, and a heteroaryl group having 5 to 60 ring atoms, or are selected from the group consisting of, 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-mentioned condensed ring is a C3-C 60 a condensed aliphatic ring (specifically, a C3-C 30 condensed aliphatic ring), C6-C 60 a 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), C3-C 60 a spiro ring, and one or more selected from combinations thereof may be possible.

[0052] As an example, in the above [Chemical Formula 4], [Chemistry] The moiety may be selected from the group consisting of the following moieties Dz-1 to Dz-32, but is not limited thereto. [Chemistry] [Chemistry] In the above moieties Dz-1 and Dz-32, * is the bonding site with the above [Chemical Formula 4], R1 is an aryl group of C6-C 60 and specifically is a phenyl group.

[0053] In the compound represented by the above [Chemical Formula 4], 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. On the other hand, 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 is deuterium (D), 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 40 alkynyl group, a C3-C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 nuclear atoms, a C6-C 60 aryl group, a heteroaryl group having 5 to 60 nuclear atoms, a C1-C 40 alkyloxy group, a C6-C 60 aryloxy group, a C1-C 40 alkylsilyl group, a C6-C 60 arylsilyl group, a C1-C 40 alkylboron group, a C6-C 60 arylboron group, a phosphine oxide group, a C1-C 40an alkylphosphine oxide group, C6-C 60 an arylphosphine group, C6-C 60 an arylphosphine oxide group, and C6-C 60 an 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 is hydrogen, a halogen group, a cyano group, a nitro group, an amino group, a C1-C 40 alkyl group, C6-C 60 aryl group, and a heteroaryl group having 5 to 60 ring atoms may be selected from the group consisting of.

[0054] 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, a halogen, a cyano group, a nitro group, a C2-C 40 alkenyl group, C2-C 40 alkynyl group, C3-C 40 cycloalkyl group, a heterocycloalkyl group having 3 to 40 ring atoms, C1-C 40 alkyl group, C6-C 60 aryl group, a heteroaryl group having 5 to 60 ring atoms, C1-C 40 alkyloxy group, C6-C 60 aryloxy group, C1-C 40 alkylsilyl group, C6-C 60 arylsilyl group, C1-C 40 alkylboron group, C1-C 60 arylboron group, C6-C 60 arylphosphine group, C6-C 60 arylphosphine oxide group, and C6-C 60Substituted with one or more substituents selected from the group consisting of arylamine groups, or unsubstituted, and when there are a plurality of said substituents, they may be the same as or different from each other.

[0055] The compound represented by the above [Chemical Formula 4] may be a compound represented by the following [Chemical Formula 5], but is not limited thereto.

Chem.

[0056] Specifically, the compound represented by the above [Chemical Formula 4] may be a compound represented by the following [Chemical Formula 6] or [Chemical Formula 7], but is not limited thereto.

Chem.

Chem.

[0057] More specifically, the compound represented by the above [Chemical Formula 4] may be a compound represented by the following [Chemical Formula 8] or [Chemical Formula 9], but is not limited thereto.

Chem.

Chem.

[0058] The compound represented by [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-10, but is not limited to these examples.

Chemical Formula

[0059] 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, and the like.

[0060] 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, and the like.

[0061] 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, and the like.

[0062] 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, and the like.

[0063] 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 and the like.

[0064] 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 and the like.

[0065] In the present invention, "heteroaryl" means a monovalent substituent derived from a monocyclic or polycyclic aromatic hydrocarbon having 5 to 60 ring 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 and the like.

[0066] In the present invention, "alkyloxy" refers to a monovalent substituent represented by R'O-, where 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 and the like.

[0067] In the present invention, "aryloxy" refers to a monovalent substituent represented by RO-, where R means an aryl having 5 to 40 carbon atoms. Examples thereof include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy and the like.

[0068] In the present invention, "alkylsilyl" means silyl substituted with an alkyl having 1 to 40 carbon atoms, and includes not only mono-, but also di- and tri-alkylsilyl. Further, "arylsilyl" means silyl substituted with an aryl having 5 to 60 carbon atoms, and includes polyarylsilyl such as mono-, di- and tri-arylsilyl.

[0069] In the present invention, "alkylboron" means boron substituted with an alkyl having 1 to 40 carbon atoms, and "arylboron" means boron substituted with an aryl having 6 to 60 carbon atoms.

[0070] In the present invention, "alkylphosphinyl group" means a phosphine group substituted with an 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 a monoaryl or diaryl having 6 to 60 carbon atoms, and includes not only mono-, but also di-arylphosphinyl group.

[0071] In the present invention, "arylamine" means an amine substituted with an aryl having 6 to 60 carbon atoms, and includes not only mono-, but also di-arylamine.

[0072] In the present invention, the "heteroarylamine" means an amine substituted with a heteroaryl having 5 to 60 nuclear atoms, and includes not only mono- but also di-heteroarylamine.

[0073] In the present invention, the "(aryl)(heteroaryl)amine" means an amine substituted with an aryl having 6 to 60 carbon atoms and a heteroaryl having 5 to 60 nuclear atoms.

[0074] 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.

[0075] The use ratio (mixing ratio) of the first organic compound powder and the second organic compound powder is not particularly limited, and is, for example, a weight ratio of 1:99 to 99:1. As an example, the pellet may have a mixing ratio of the first organic compound powder and the second organic compound powder of 20:80 to 80:20 by weight. Since this is vapor-deposited while maintaining a certain mixing ratio, the characteristics of a uniform mixing ratio can be stably ensured during vapor deposition.

[0076] The particle size and shape of the first organic compound powder and the second organic compound powder are not particularly limited as long as they are well-known in the art, and as an example, they may be white or light yellow powders.

[0077] In the pellet of the present invention, not only are the first organic compound powder and the second organic compound powder uniformly mixed and pressed, but also the first organic compound powder and the second organic compound powder are respectively arranged in a certain region and pressed in a predetermined pattern. Thus, when the pellet of the present invention is partitioned into a first region portion containing the first organic compound and a second region portion containing the second organic compound in a certain pattern, compared with the case where the first organic compound and the second organic compound are mixed, during the deposition of a thin film by a continuous process (for example, a roll-to-roll process), the mixing ratio of the first organic compound and the second organic compound can be kept constant at a set ratio, so that the reproducibility of the thin film can be improved. In particular, when the pellet of the present invention has a form in which one of the first organic compound and the second organic compound having high sublimability is wrapped by the other organic compound (see (a) and (g) of FIG. 1), compared with other forms, a thin film can be formed while keeping the set ratio constant during the deposition of the thin film.

[0078] Specifically, as shown in FIG. 1, the pellet 10 of the present invention includes a first region portion 11 to which the first organic compound powder is pressed, and a second region portion 12 that is integrally arranged with the first region portion 11 and to which the second organic compound powder is pressed. At this time, the first and second region portions 11 and 12 may be arranged in various patterns.

[0079] In one example, as shown in FIGS. 1(a) and 1(g), the first region portion 11 and the second region portion 12 of the pellet 10 of the present invention may be alternately arranged in the radial direction from the center to the outer periphery.

[0080] In another example, as shown in FIGS. 1(c), 1(d), 1(h), 1(i), 1(j), and 1(f), the first region portion 11 and the second region portion 12 of the pellet 10 of the present invention may be arranged in the length direction (for example, up and down). At this time, the first region portion 11 and the second region portion 12 may be alternately arranged (FIGS. 1(d) and 1(i)).

[0081] In another example, as shown in FIGS. 1(e), 1(j), and 1(k), in the pellet 10 of the present invention, the first region portion 11 and the second region portion 12 may be alternately arranged in the circumferential direction. At this time, the first region portion 11 and the second region portion 12 may be alternately arranged vertically.

[0082] In another example, as shown in FIG. 1(l) of the pellet 10 of the present invention, in addition to the first region portion 11 and the second region portion 12, a third region portion 13 to which a third organic compound powder different from the first organic compound and the second organic compound is pressure-bonded, ···, an nth region portion (not shown) to which an nth organic compound powder is pressure-bonded (4 ≦ n, specifically, 4 ≦ n ≦ 6) may be further included.

[0083] The shape of the pellet is not particularly limited and may be, for example, a polyhedron, a cylinder, a sphere, or the like.

[0084] As described above, the pellet of the present invention having a predetermined shape may have a BET specific surface area smaller than that of a simple mixture of the first organic compound powder and the second organic compound powder.

[0085] Further, the pellet of the present invention may have a surface resistance smaller than that of a simple mixture of the first organic compound powder and the second organic compound powder.

[0086] Furthermore, unlike a simple mixture of the first organic compound and the second organic compound, the pellet of the present invention can be vapor-deposited while maintaining a constant mixing ratio of the first organic compound and the second organic compound before and after vapor deposition even when forming a thin film by a continuous process. Therefore, the pellet of the present invention can form a thin film having a characteristic of a uniform mixing ratio during vapor deposition of the thin film by a continuous process. In one example, when vapor-depositing a thin film by a continuous process, the rate of change over time before and after vapor deposition of the pellet of the present invention is about 1% or less, specifically, about 0.01 to 0.8%.

[0087] The pellets of the present invention can be manufactured by pellet molding methods well-known in the art. However, since the pellets of the present invention are pressurized without heat treatment, they do not chemically change, and thus have the same chemical and physical properties as the powders of the first organic compound, the second organic compound, and simple mixtures thereof.

[0088] In one example, the pellets of the present invention are manufactured by injecting two or more kinds of organic compound powders containing the first organic compound powder and the second organic compound powder into a mold, and then applying a pressure of about 20,000 to 40,000 kgf / cm 2 to the two or more kinds of organic compound powders and performing injection molding without heat treatment.

[0089] <Organic EL element> The present invention also provides an organic EL element using the pellets as described above.

[0090] Specifically, as shown in FIGS. 2 to 4, the organic EL element according to the present invention includes an anode 100, a cathode 200, and one or more organic layers 300 interposed between the anode and the cathode. At least one of the one or more organic layers is formed of the above-described pellets and is a homogeneous thin film containing the first organic compound and the second organic compound.

[0091] The one or more organic layers 300 include any one or more of a hole injection layer 310, a hole transport layer 320, a light-emitting layer 330, an electron transport auxiliary layer 360, an electron transport layer 340, and an electron injection layer 350. At least one of the organic layers 300 can be formed of the above-described pellets and is a homogeneous thin film containing the first organic compound and the second organic compound. At this time, the first organic compound is a hole-transporting organic compound, and the second organic compound is an electron-transporting organic compound.

[0092] In one example, the homogeneous thin film may be the light-emitting layer 330. At this time, the first organic compound is a hole-transporting host, and the second organic compound is an electron-transporting host.

[0093] The mixing ratio of the first organic compound and the second organic compound is a weight ratio of 1:99 to 99:1, preferably a weight ratio of 20:80 to 80:20.

[0094] In addition to the first organic compound and the second organic compound, the light-emitting layer may further contain a host and / or a dopant known in the art. At this time, the total content of the first organic compound and the second organic compound is 0% by weight or more and 100% by weight or less based on the total weight of the host.

[0095] Also, the total weight of the host is about 70 to 99.9% by weight based on the total weight of the light-emitting layer, and the content of the dopant is about 0.1 to 30% by weight based on the total weight of the light-emitting layer.

[0096] The structure of the organic EL element of the present invention as described above is not particularly limited. For example, on a substrate, an anode 100, one or more organic layers 300, and a cathode 200 are sequentially laminated (see FIGS. 2 to 4). Further, although not shown, a structure in which an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic layer may also be used.

[0097] In one example, as shown in FIG. 2, the organic EL element has a structure in which an anode 100, a hole injection layer 310, a hole transport layer 320, a light-emitting layer 330, an electron transport layer 340, and a cathode 200 are sequentially laminated on a substrate. Optionally, as shown in FIG. 3, an electron injection layer 350 may be disposed between the electron transport layer 340 and the cathode 200. Also, an electron transport auxiliary layer 360 may be disposed between the light-emitting layer 330 and the electron transport layer 340 (see FIG. 4).

[0098] The organic EL element according to the present invention can be manufactured by forming the organic material layer and the electrodes by materials and methods known in the art, except that at least one of the organic material layers 300 (for example, the light emitting layer 330) is a uniform thin film formed of the pellets.

[0099] The organic material layer can be formed by dry film formation methods such as vacuum evaporation, sputtering, plasma plating, ion plating, etc., but is not limited thereto.

[0100] Examples of the substrate that can be used in the present invention include, but are not limited to, silicon wafers, quartz, glass plates, metal plates, plastic films, and sheets.

[0101] Examples of the anode material include metals such as vanadium, chromium, copper, zinc, and gold or alloys thereof; metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); combinations of metals and oxides such as ZnO:Al or SnO2:Sb; conductive polymers such as polythiophene, poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDT), polypyrrole, or polyaniline; and carbon black, etc., but are not limited thereto.

[0102] Examples of the cathode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or alloys thereof; and multilayer structured materials such as LiF / Al or LiO2 / Al, etc., but are not limited thereto.

[0103] In addition, the materials for the hole injection layer, hole transport layer, light emitting layer, and electron injection layer are not particularly limited, and substances known in the art can be used without limitation.

Examples

[0104] Hereinafter, the present invention will be described in detail with reference to examples. However, the examples described below are merely illustrative of the present invention, and the present invention is not limited by these examples.

[0105] <Preparation Example 1-1> Synthesis of Cz-D1

Chemical formula

[0106] After completion of the reaction, the mixture was extracted with ethyl acetate, 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)

[0107] <Preparation Example 1-2> Synthesis of Cz-D2

Chemical formula

[0108] <Preparation Example 1-3> Synthesis of Cz-D3

Chemical formula

[0109] <Preparation Example 1-4> Synthesis of Cz-D4

Chemical formula

[0110] <Preparation Example 2-1> Synthesis of Cz-D5

Chemical formula

[0111] <Preparation Example 2-2> Synthesis of Cz-D6

Chemical formula

[0112] <Preparation Example 2-3> Synthesis of Cz-D7

Chemical formula

[0113] <Preparation Example 2-4> Synthesis of Cz-D8

Chemical formula

[0114] <Preparation Example 3-1> Synthesis of Cz-D9

Chemical formula

[0115] <Preparation Example 3-2> Synthesis of Cz-D10

Chemical formula

[0116] <Preparation Example 3-3> Synthesis of Cz-D11

Chemical formula

[0117] <Preparation Example 3-4> Synthesis of Cz-D12

Chemical formula

[0118] <Preparation Example 4-1> Synthesis of Cz-D13

Chemical formula

[0119] <Preparation Example 4-2> Synthesis of Cz-D14

Chemical formula

[0120] <Preparation Example 4-3> Synthesis of Cz-D15

Chemical formula

[0121] <Preparation Example 4-4> Synthesis of Cz-D16

Chemical formula

[0122] <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

[0123] After completion of the reaction, the mixture was extracted with ethyl acetate, the moisture was removed with MgSO4, and 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)

[0124] <Step 2> Synthesis of BCz-D1

Chemical formula

[0125] 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:EA = 7:1 (v / v)) to obtain BCz-D1 (71.1 g, yield 66%). Mass (theoretical value: 422.59, measured value: 422 g / mol)

[0126] <Preparation Example 5-2> Synthesis of BCz-D2

Chemical formula

[0127] <Preparation Example 5-3> Synthesis of BCz-D3

Chemical formula

[0128] <Preparation Example 5-4> Synthesis of BCz-D4

Chemical Structure

[0129] [Synthesis Example 1] Synthesis of A-1

Chemical Structure

[0130] [Synthesis Example 2] Synthesis of A-2

Chemical Structure

[0131] [Synthesis Example 3] Synthesis of A-3 [Chemical formula] Compound A-3 (13.2 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)

[0132] [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)

[0133] [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)

[0134] [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)

[0135] [Synthesis Example 7] Synthesis of A-7 [Chem.] Except for using Cz-D7 (10.0 g, 23.6 mmol) obtained in Preparation Example 2-3 instead of Cz-D1 used in Synthesis Example 1, the target compound A-7 (8.83 g, yield 50%) was obtained in the same manner as in Synthesis Example 1. Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0136] [Synthesis Example 8] Synthesis of A-8 [Chem.] Except for using Cz-D8 (10.0 g, 23.6 mmol) obtained in Preparation Example 2-4 instead of Cz-D1 used in Synthesis Example 1, the target compound A-8 (9.89 g, yield 56%) was obtained in the same manner as in Synthesis Example 1. Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0137] [Synthesis Example 9] Synthesis of A-9 [Chem.] Except for using Cz-D9 (9.3 g, 23.6 mmol) obtained in Preparation Example 3-1 instead of Cz-D1 used in Synthesis Example 1, the target compound A-9 (8.41 g, yield 53%) was obtained in the same manner as in Synthesis Example 1. Mass (theoretical value: 670.93, measured value: 670 g / mol)

[0138] [Synthesis Example 10] Synthesis of A-10 [Chem.] Instead of Cz-D1 used in Synthesis Example 1, A-10 (8.66 g, yield 49%), the target compound, was obtained in the same manner as in Synthesis Example 1, except that Cz-D10 (10.0 g, 23.6 mmol) obtained in Preparation Example 3-2 was used. Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0139] [Synthesis Example 11] Synthesis of A-11

Chemical Structure

[0140] [Synthesis Example 12] Synthesis of A-12

Chemical Structure

[0141] [Synthesis Example 13] Synthesis of A-13

Chemical Structure

[0142] [Synthesis Example 14] Synthesis of A-14 [Chemical formula] Except for using Cz-D14 (10.0 g, 23.6 mmol) obtained in Preparation Example 4-2 instead of Cz-D1 used in Synthesis Example 1, the target compound A-14 (10.78 g, yield 61%) was obtained in the same manner as in Synthesis Example 1. Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0143] [Synthesis Example 15] Synthesis of A-15 [Chemical formula] Except for using Cz-D15 (10.0 g, 23.6 mmol) obtained in Preparation Example 4-3 instead of Cz-D1 used in Synthesis Example 1, the target compound A-15 (11.13 g, yield 63%) was obtained in the same manner as in Synthesis Example 1. Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0144] [Synthesis Example 16] Synthesis of A-16 [Chemical formula] Except for using Cz-D16 (10.0 g, 23.6 mmol) obtained in Preparation Example 4-4 instead of Cz-D1 used in Synthesis Example 1, the target compound A-16 (9.02 g, yield 51%) was obtained in the same manner as in Synthesis Example 1. Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0145] [Synthesis Example 17] Synthesis of B-1 [Chemical formula] Under a nitrogen stream, BCz-D2 (10.0 g, 20.1 mmol) obtained in Preparation Example 5-2, Cz-D1 (7.9 g, 24.1 mmol) obtained in Preparation Example 1-1, Pd(OAc)2 (1.15 g, 1.0 mmol), P(t-Bu)3 (0.49 ml, 2.0 mmol), NaO(t-Bu) (3.85 g, 40.1 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 B-1 (10.2 g, yield 62%). Mass (theoretical value: 747.02, measured value: 747 g / mol)

[0146] [Synthesis Example 18] Synthesis of B-2

Chemical Structure

[0147] [Synthesis Example 19] Synthesis of B-3

Chemical Structure

[0148] [Synthesis Example 20] Synthesis of B-4

Chemical Structure

[0149] [Synthesis Example 21] Synthesis of C-1

Chemical Structure

[0150] [Synthesis Example 22] Synthesis of C-2

Chemical Structure

[0151] [Synthesis Example 23] Synthesis of C-3

Chemical Structure

[0152] [Synthesis Example 24] Synthesis of C-4

Chemical formula

[0153] [Synthesis Example 25] Synthesis of D-1

Chemical formula

[0154] [Synthesis Example 26] Synthesis of D-2

Chemical formula

[0155] [Synthesis Example 27] Synthesis of D-3

Chemical Structure

[0156] [Synthesis Example 28] Synthesis of D-4

Chemical Structure

[0157] [Preparation Example 6] Synthesis of DBF-1 <Step 1> Synthesis of 4-(3-chlorophenyl)-6-phenyldibenzothiophene

Chemical Structure

[0158] 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: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)

[0159] <Step 2> Synthesis of DBF-1

Chemical formula

[0160] After completion of the reaction, the mixture was extracted with ethyl acetate, the moisture 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)

[0161] [Preparation Example 7] Synthesis of DBF-2 <Step 1> Synthesis of 4-(4-chlorophenyl)-6-phenyldibenzothiophene

Chemical formula

[0162] 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)

[0163] <Step 2> Synthesis of DBF-2

Chemical formula

[0164] After the reaction was completed, 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)

[0165] [Preparation Example 8] Synthesis of DBF-3 [Step 1] Synthesis of 3-(3-chlorophenyl)-6-phenyldibenzofuro[2,3-b]pyridine [Chemical formula] Under a nitrogen stream, 4,4,5,5-tetramethyl-2-(6-phenyldibenzofuro[2,3-b]pyridin-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.

[0166] After the reaction was completed, 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-phenyldibenzofuro[2,3-b]pyridine (68.0 g, yield 71%). Mass (theoretical value: 354.83, measured value: 354 g / mol)

[0167] [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.

[0168] After completion of the reaction, the mixture was extracted with ethyl acetate, then the moisture was removed with MgSO4, and the product 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)

[0169] [Preparation Example 9] Synthesis of DBF-4 <Step 1> Synthesis of 1-(3-chlorophenyl)-6-phenyldibenzothiophene

Chemical formula

[0170] After completion of the reaction, the mixture was extracted with methylene chloride, and MgSO4 was added followed by filtration. Next, the solvent was removed from the obtained organic layer, and the product 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)

[0171] <Step 2> Synthesis of DBF-4

Chem.

[0172] After completion of the reaction, the mixture was extracted with ethyl acetate, the water was removed with MgSO4, and purification was performed 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)

[0173] [Preparation Example 10] Synthesis of DBF-5 <Step 1> Synthesis of 1-(3-chlorophenyl)-9-phenyldibenzothiophene

Chem.

[0174] 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: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)

[0175] <Step 2> Synthesis of DBF-5

Chemical formula

[0176] After completion of the reaction, the mixture was extracted with ethyl acetate, the moisture was removed with MgSO4, and it was purified 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)

[0177] [Synthesis Example 29] Synthesis of E-1

Chemical formula

[0178] 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)

[0179] [Synthesis Example 30] Synthesis of E-2

Chemical formula

[0180] [Synthesis Example 31] Synthesis of E-3

Chemical formula

[0181] [Synthesis Example 32] Synthesis of E-4

Chemical formula

[0182] [Synthesis Example 33] Synthesis of E-5

Chemical formula

[0183] [Synthesis Example 34] Synthesis of E-6 [Chemical Formula] Instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine used in Synthesis Example 29, 2-([1,1’:3’,1”-terphenyl]-5’-yl)-4-chloro-6-(dibenzo[b,d]furan-3-yl)-1,3,5-triazine (13.7 g, 26.9 mmol) was used. Otherwise, in the same manner as in Synthesis Example 29, the target compound E-6 (9.6 g, yield 54%) was obtained. Mass (theoretical value: 793.93, measured value: 793 g / mol)

[0184] [Synthesis Example 35] Synthesis of E-7 [Chemical Formula] Instead of DBF-1 (10.0 g, 22.4 mmol) used in Synthesis Example 29, DBF-4 (10.0 g, 22.4 mmol) obtained in Preparation Example 9 was used. Instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine, 2-([1,1’-biphenyl]-4-yl)-4-(3-bromophenyl)-6-phenyl-1,3,5-triazine (12.5 g, 26.9 mmol) was used. Otherwise, in the same manner as in Synthesis Example 29, the target compound E-7 (9.8 g, yield 62%) was obtained. Mass (theoretical value: 703.85, measured value: 703 g / mol)

[0185] [Synthesis Example 36] Synthesis of E-8 [Chemical Formula] Instead of using DBF-1 (10.0 g, 22.4 mmol) used in Synthesis Example 29, DBF-3 (10.0 g, 22.4 mmol) obtained in Preparation Example 8 was used. Instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine, 2-(3-bromophenyl)-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine (12.9 g, 26.9 mmol) was used. Otherwise, in the same manner as in Synthesis Example 29, the target compound E-8 (10.8 g, yield 67%) was obtained. Mass (theoretical value: 717.83, measured value: 717 g / mol)

[0186] [Synthesis Example 37] Synthesis of E-9 [Chemical formula] Instead of using DBF-1 (10.0 g, 22.4 mmol) used in Synthesis Example 29, DBF-3 (10.0 g, 22.4 mmol) obtained in Preparation Example 8 was used. Instead of 2-chloro-4-(dibenzo[b,d]furan-3-yl)-6-phenyl-1,3,5-triazine, 2-([1,1'-biphenyl]-4-yl)-4-(3-bromophenyl)-6-phenyl-1,3,5-triazine (12.5 g, 26.9 mmol) was used. Otherwise, in the same manner as in Synthesis Example 29, the target compound E-9 (11.4 g, yield 72%) was obtained. Mass (theoretical value: 703.85, measured value: 703 g / mol)

[0187] [Synthesis Example 38] Synthesis of E-10 [Chemical formula] Instead of using DBF-1 (10.0 g, 22.4 mmol) used in Synthesis Example 29, DBF-5 (10.0 g, 22.4 mmol) obtained in Preparation Example 10 was used. Instead of 2-chloro-4-(dibenzo[b,d]fur-3-yl)-6-phenyl-1,3,5-triazine, 2-([1,1'-biphenyl]-3-yl)-4-(3-bromophenyl)-6-phenyl-1,3,5-triazine (12.5 g, 26.9 mmol) was used. Otherwise, in the same manner as in Synthesis Example 29, the target compound E-10 (10.4 g, yield 66%) was obtained. Mass (theoretical value: 703.85, measured value: 703 g / mol)

[0188] [Example 1] Production of Pellet P1 and Fabrication of Green Organic EL Device Compound A-1 having hole characteristics and compound E-1 having electron characteristics were uniformly mixed at a weight ratio of 6:4. Then, the above mixture was pelletized under a pressure of 20,000 kgf / cm 2 to obtain pellet P1 as shown in Fig. 1(a). Then, a green organic EL device was fabricated according to the following procedure. At this time, the above compound A-1 is a first organic compound having hole characteristics and was obtained in Synthesis Example 1, and the above compound E-1 is a second organic compound having electron characteristics and was obtained in Synthesis Example 29.

[0189] First, a glass substrate with a 1500 Å-thick thin film coating of ITO (Indium Tin Oxide) was washed with distilled water ultrasonic. After the washing with distilled water was completed, ultrasonic washing was performed with solvents such as isopropyl alcohol, acetone, and methanol, and after drying, it was transferred to a UV ozone washer (Power sonic 405, manufactured by Facsintec Co., Ltd.). Then, the above substrate was washed with UV for 5 minutes and transferred to a vacuum evaporator.

[0190] On the thus-prepared ITO transparent electrode, an organic EL element was fabricated by laminating in the order of m-MTDATA (60 nm) / TCTA (80 nm) / 90 wt% of pellet P1 + 10 wt% of Ir(ppy)3 (300 nm) / BCP (10 nm) / Alq3 (30 nm) / LiF (1 nm) / Al (200 nm).

[0191] The structures of m-MTDATA, TCTA, Ir(ppy)3, and BCP are as follows.

Chemical formula

[0192] [Examples 2 to 280] Production of pellets P2 to P280 and fabrication of green organic EL elements Pellets P2 to P280 and green organic EL elements using them were fabricated in the same manner as in Example 1, except that compounds A-2 to D-4 described in Table 2 were used respectively instead of compound A-1 used as the first organic compound in Example 1, and compounds E-2 to E-10 described in Table 2 were used respectively instead of compound E-1 used as the second organic compound. At this time, the mixing ratio of the compound used as the first organic compound and the compound used as the second organic compound was the same as the mixing ratio of compound A-1 and compound E-1 in Example 1.

[0193] [Example 281] Production of pellet P281 and fabrication of green organic EL element Pellet P281 and a green organic EL element using it were fabricated in the same manner as in Example 1, except that compound A-1 and compound E-1 in Example 1 were mixed at a weight ratio of 5:5.

[0194] [Example 282] Production of pellet P282 and fabrication of green organic EL element Pellet P282 and a green organic EL element using it were fabricated in the same manner as in Example 1, except that compound A-1 and compound E-1 in Example 1 were mixed at a weight ratio of 7:3.

[0195] [Comparative Example 1] Fabrication of Green Organic EL Element A green organic EL element was fabricated in the same manner as in Example 1, except that comA-1, which is a simple mixture of Compound A-1 and Compound E-1 (weight ratio of Compound A-1:Compound E-1 = 6:4), was used instead of pellet P1 used as the light-emitting host material during the formation of the light-emitting layer. At this time, unlike pellet P1, comA, which is the above simple mixture, uniformly mixes Compound A-1 and Compound E-1, but no pressure molding was performed under high pressure. The above Compound A-1 and Compound E-1 are as described in Example 1, respectively.

[0196] [Comparative Example 2] Fabrication of Green Organic EL Element A simple mixture comB and a green organic EL element using the same were fabricated in the same manner as in Comparative Example 1, except that Compound A-1 and Compound E-1 in Comparative Example 1 were mixed at a weight ratio of 5:5.

[0197] [Comparative Example 3] Fabrication of Green Organic EL Element A simple mixture comC and a green organic EL element using the same were fabricated in the same manner as in Comparative Example 1, except that Compound A-1 and Compound E-1 in Comparative Example 1 were mixed at a weight ratio of 7:3.

[0198] [Experimental Example 1] Measurement of Maximum Emission Wavelength of Pellets The pellets P1 to P280 obtained in Examples 1 to 280 were formed into films, and their maximum emission wavelengths were measured. The results are shown in Table 1. At this time, the maximum emission wavelengths of Compounds A-1 to D-4 and Compounds E-1 to E-10, which are the raw materials of each pellet, were measured, and the maximum emission wavelength of comA, which is a simple mixture of Comparative Example 1, was measured as a control group.

[0199]

Table 1

[0200] As shown in Table 1 above, it was confirmed that the pellets P1 to P280 (Examples 1 to 280) according to the present invention have the same maximum emission wavelength as the compound having a relatively long wavelength compared to each raw material compound (compounds A-1 to D-4 and compounds E-1 to E-10).

[0201] [Experimental Example 2] Performance Evaluation of Organic Light-Emitting Devices For the green organic EL devices fabricated in Examples 1 to 280 and Comparative Example 1, the driving voltage, current efficiency, and lifetime (T 2 ) at a current density of 10 mA / cm 97 were measured, and the results are shown in Table 2 below.

[0202]

Table 2

[0203] As shown in Table 2, the green organic EL device of Example 1 using the pellet P1 according to the present invention as the host material of the light-emitting layer has a lower driving voltage, higher current efficiency, and longer life characteristics compared to the green organic EL device of Comparative Example 1 using the simple mixture comA. Thus, when the pellet according to the present invention is used as the organic material layer material (for example, the host material of the light-emitting layer) of the OLED, it was found that the performance of the organic EL light device is improved.

[0204] [Experimental Example 3] In Examples 1, 281, and 282 and Comparative Examples 1 to 3, when manufacturing the green organic EL device, a thin film was formed by a continuous process, and the change in the weight ratio of Compound A-1 and Compound E-1 in the pellets P1, P281, P282, and the simple mixtures comA to comC before and after the process was measured, and the results are shown in Table 3 below.

[0205]

Table 3

[0206] As shown in Table 3 above, when a thin film of the light-emitting layer of the green organic EL device was formed by a continuous process using the pellets P1, P281, P282 (Examples 1, 281, 282) according to the present invention, compared with the case where a thin film of the light-emitting layer of the green organic EL device was formed by a continuous process using a simple mixture of Compound A-1 and Compound E-1 (Comparative Examples 1 to 3), it was confirmed that a thin film with good reproducibility and homogeneity was obtained.

Claims

1. Two or more organic compound powders containing a first organic compound powder and a second organic compound powder are pressure-bonded, An organic EL element pellet having the same maximum emission wavelength as the maximum emission wavelength of the organic compound having a longer emission wavelength among the first organic compound and the second organic compound.

2. The organic EL element pellet according to claim 1, having the same maximum emission wavelength as the maximum emission wavelength of the mixed powder of the first organic compound powder and the second organic compound powder.

3. A first region portion where the first organic compound powder is pressure-bonded; and A second region portion that is integrally arranged with the first region portion and where the second organic compound powder is pressure-bonded; The organic EL element pellet according to claim 1, comprising:

4. The organic EL element pellet according to claim 3, wherein the first region portion and the second region portion are alternately arranged in the radial direction from the center to the outer periphery.

5. The organic EL element pellet according to claim 3, wherein the first region portion and the second region portion are arranged vertically.

6. The organic EL element pellet according to claim 5, wherein the first region portion and the second region portion are alternately arranged.

7. The organic EL element pellet according to claim 3, wherein the first region portion and the second region portion are alternately arranged in the circumferential direction.

8. The organic EL element pellet according to claim 7, wherein the first region portion and the second region portion are alternately arranged vertically.

9. The organic EL element pellet according to claim 3, wherein the pellet has a shape selected from the group consisting of a polyhedron, a cylinder, and a sphere.

10. The organic EL element pellet according to claim 1, wherein the content ratio of the first organic compound powder and the second organic compound powder is a weight ratio of 1:99 to 99:

1.

11. The organic EL element pellet according to claim 1, wherein both the first organic compound powder and the second organic compound powder are sublimable powders.

12. The first organic compound is a hole-transporting organic compound, The organic EL element pellet according to claim 1, wherein the second organic compound is an electron-transporting organic compound.

13. The organic EL element pellet according to claim 12, wherein the hole-transporting organic compound is a hole-transporting host.

14. The organic EL element pellet according to claim 12, wherein the hole-transporting host is a carbazole-based compound.

15. The above electron-transporting organic compound is a pellet for an organic EL device according to claim 12, which is an electron-transporting host.

16. The above electron-transporting host is an azine compound, and the pellet for an organic EL device according to claim 15.

17. The pressure of 20,000 to 40,000 kgf / cm is applied to the above two or more kinds of organic compound powders, and the pellet for an organic EL element according to claim 1, which is a molded body injection-molded under the condition of not performing heat treatment. ２ ​

18. The first organic compound powder and the second organic compound powder have a vapor deposition temperature difference of 0 to 30°C under a pressure of 10 －６ Torr, and the pellet for an organic EL element according to claim 1.

19. The pellet for an organic EL device according to claim 1, having a BET specific surface area smaller than that of a simple mixture of the above first organic compound powder and the second organic compound powder.

20. The pellet for an organic EL device according to claim 1, having a surface resistance smaller than that of a simple mixture of the above first organic compound powder and the second organic compound powder.

21. An anode; a cathode; one or more organic layers interposed between the above anode and cathode; At least one of the above one or more organic layers is a homogeneous thin film containing the above first organic compound and the second organic compound using the pellet according to any one of claims 1 to 20, and the organic EL device.

Images