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WO2005103195A1 - Solide émettant une phosphorescence, élément électroluminescent organique et dispositif d'électroluminescence organique - Google Patents

Solide émettant une phosphorescence, élément électroluminescent organique et dispositif d'électroluminescence organique Download PDF

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Publication number
WO2005103195A1
WO2005103195A1 PCT/JP2004/004485 JP2004004485W WO2005103195A1 WO 2005103195 A1 WO2005103195 A1 WO 2005103195A1 JP 2004004485 W JP2004004485 W JP 2004004485W WO 2005103195 A1 WO2005103195 A1 WO 2005103195A1
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Prior art keywords
phosphorescent
solid according
organometallic complex
phosphorescent solid
organic
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English (en)
Japanese (ja)
Inventor
Tasuku Satoh
Wataru Sotoyama
Norio Sawatari
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Fujifilm Holdings Corp
Fujitsu Ltd
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Fujitsu Ltd
Fuji Photo Film Co Ltd
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Priority to PCT/JP2004/004485 priority Critical patent/WO2005103195A1/fr
Priority to TW093108735A priority patent/TWI245586B/zh
Publication of WO2005103195A1 publication Critical patent/WO2005103195A1/fr
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
    • C09K11/88—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing selenium, tellurium or unspecified chalcogen elements
    • C09K11/881—Chalcogenides
    • C09K11/883—Chalcogenides with zinc or cadmium
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
    • C09K11/62—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing gallium, indium or thallium
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
    • C09K11/74—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing arsenic, antimony or bismuth
    • C09K11/7492—Arsenides; Nitrides; Phosphides
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
    • C09K11/89—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing mercury
    • C09K11/892—Chalcogenides
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission

Definitions

  • the present invention relates to a phosphorescent solid containing a phosphorescent organometallic complex having a specific ligand, a light-emitting device using the same, and in particular, an organic electroluminescence device (hereinafter referred to as “electroluminescence”).
  • EL organic electroluminescence
  • EL organic electroluminescence
  • an organic EL device using the same such as an organic EL display and an organic EL lighting device.
  • Organic EL devices are reported as stacked devices in which organic thin films with hole-transporting and electron-transporting properties are stacked (for example, CW Tangand SA V an S 1 yke), Applied Physics Letters, No. 51 Vol., P. 913, 1987), is expected to be applied to flat panel displays as display elements with features such as self-luminous light and high-speed response. It has attracted interest as an area light emitting device.
  • the stacked organic EL element basically has a configuration of a positive electrode / a hole transport layer / a light emitting layer / a Z electron transport layer / a negative electrode.
  • the light-emitting layer may have a configuration in which a hole transport layer or an electron transport layer also has the function as in the case of the two-layer element of Ta1gandVanS1yke described above.
  • the luminescent layer In order to obtain an organic EL device with high luminous efficiency, the luminescent layer needs to have high luminous efficiency.
  • a dye-doped film in which a small amount of highly fluorescent dye molecules are doped as a guest in a host material as a main component has been devised. (Eg, CW Tang, SA Van S 1 yke, and CH Chain), Journalof Applied Physics, Vol. 65, p. 3610, 1989).
  • a metal complex having a tridentate ligand described in JP-A-2002-363552 can be cited as an example.
  • it consists of two cognate bonds between platinum and nitrogen and one coordination bond between platinum and carbon, and these two nitrogen and carbon are bonded in the order of N, N and C.
  • a technique using an organometallic complex having a coordination ligand (N—N′C) as a light emitting material of an organic EL device is disclosed.
  • N—N′C coordination ligand
  • the phosphorescence of this complex is not sufficient at room temperature, and the organic EL device of the above-mentioned known example has a low level and a low luminous efficiency.
  • organometallic complexes having the structure of N "C” N-type tridentate ligands are better than N-N "C-type in solution. It has been reported by JAG Wi 11 i ams et al. (I norg. Chem., Vol. 42, p. 8609-8611, 2003).
  • Emission from organic matter is broadly classified into fluorescence and phosphorescence depending on the nature of the excited state that causes light emission.
  • fluorescent light has been used in organic EL devices because common organic substances do not emit phosphorescence.
  • the phosphorescent state will be generated four times more likely than the fluorescent state.
  • it has attracted attention as a means of increasing efficiency.
  • there are very few materials that emit strong phosphorescence at room temperature and the narrowest selection of materials is the biggest problem at present. Disclosure of the invention
  • the present invention examines a phosphorescent light-emitting material suitable for an organic EL device to improve the luminous efficiency. It is an object of the present invention to provide a phosphorescent solid having high phosphorescence, an organic EL element and an organic EL device using the phosphorescent solid. Still other objects and advantages of the present invention will become apparent from the following description.
  • a metal complex having a specific tridentate ligand and a halogen atom as ligands emits particularly strong phosphorescence in the solid state, and this is used as a light emitting material.
  • the organic EL device that was used was found to emit light with high efficiency.
  • two nitrogen atoms and a carbon atom between them, which are bonded through force and bond, to a central metal atom are coordinated to the two metal atoms.
  • a phosphorescent solid containing an organometallic complex formed by coordinating at least one of a binding tridentate ligand and at least one halogen atom is formed.
  • the phosphorescent solid contains an organometallic complex having a structure represented by the following formula (1):
  • M represents a metal atom
  • X represents a halogen atom
  • Ar 1, Ax Ar 3 each independently also represent an annular structure T have a substituent
  • Ar 1 one The bond of Ar 2 and Ar 2 — Ar 3 may be a single bond or a double bond.
  • M and Ar 1 and M and Ar 3 have a M—N coordination bond, and M and Ar 2 with direct coupling of M- C and.
  • substituents Ar 1, Ar 2, a r 3 respectively, Ar 1, Ar 2, a r 3 above and between each other a r 1 and a r 2 and a r 2 and Ar 3 may be bonded to each other to form a cyclic structure.
  • a phosphorescent solid comprises two or more nitrogen atoms and one carbon atom coordinated with at least one of a tridentate ligand and a halogen atom, each of which coordinates and binds to a central metal atom.
  • the complex has a structural portion represented by the following formula (2);
  • M and X are the same as those in the formula (1).
  • Y is each independently a carbon atom or a nitrogen atom.
  • the N—Y bond part is A r in the formula (1).
  • the benzene nucleus may have a substituent, which constitutes the — part of 1 or Ar 3.
  • the bond other than the bond between the ligand and the central metal atom may be a single bond or a double bond. It may be a combination.
  • the organometallic complex has a structural part represented by the following formula (3);
  • M and X are the same as in the formula (1).
  • the benzene nuclei may have a substituent independently of each other, and the substituents may be in the same or adjacent ring. May be bonded to each other.
  • a ⁇ and mosquitoes independently, comprise an aromatic monocyclic or polycyclic, it and A r 1 and A r 3 are the same, an organic metal complex, and one tridentate ligand, a C 9.It consists of a chromium atom and one central metal atom, that the organometallic complex is electrically neutral in a solid state, and that the organometallic complex can form a film by vacuum deposition.
  • the organometallic complex of purity that the central metal atom is platinum, organic materials having an organometallic complex, the first excited triplet excitation energy higher than that of the organic metal complex
  • phosphorescent solid of the present invention very strong phosphorescence can be realized in a solid state.
  • organic material comprising the above-mentioned phosphorescent solid.
  • electroluminescent device is provided. '
  • a phosphorescent solid in the light-emitting layer a phosphorescent solid that functions as a host or a guest; the light-emitting layer contains a phosphorescent solid and a low-molecular host material; It is preferable to contain a phosphorescent solid and a polymer host material, and to contain the phosphorescent solid in the color conversion layer.
  • an organic EL device having significantly improved luminous efficiency can be realized.
  • an organic electroluminescent device using the above-described organic electroluminescent element more specifically, an organic electroluminescent display or an organic electroluminescent lighting device Is provided.
  • a very strong phosphorescent light can be realized in a solid state, and by using the phosphorescent light in an organic EL device, the luminous efficiency can be greatly improved. Power.
  • FIG. 1 is a diagram exemplifying a structural part represented by Expression (4).
  • FIG. 2 is a diagram showing an example of Ar 1 and Ar 3 .
  • Figure 3 is a diagram showing an example of A r 2.
  • FIG. 4 is a diagram illustrating a low-molecular host material.
  • FIG. 5 is a diagram illustrating a canolebazole compound.
  • FIG. 6 is a diagram illustrating an example of Ar in FIG.
  • FIG. 7 is a diagram illustrating the linking group R in FIG.
  • FIG. 8 is a diagram showing the structure of CBP.
  • FIG. 9 is a diagram illustrating a polymer host material.
  • FIG. 10 is a diagram showing the structure of starburst amine.
  • FIG. 11 is a diagram showing the structure of TPD.
  • FIG. 12 is a diagram showing the structure of A 1 q.
  • FIG. 13 is a diagram exemplifying a material having a shorter light absorption edge than the phosphorescent solid according to the present invention.
  • FIG. 14 is a diagram showing the structure of DCJTB.
  • FIG. 15 is a schematic side sectional view of an organic EL device.
  • FIG. 16 is another schematic side sectional view of the organic EL device.
  • FIG. 17 is a diagram showing a synthesis route of dpt.
  • FIG. 18 is a diagram showing a synthesis route of Pt (dpt) CI.
  • FIG. 19 is a diagram showing a method for measuring a phosphorescence quantum yield.
  • FIG. 20 is a diagram showing the molecular structure of the organometallic complex used in the comparative example.
  • FIG. 21 is a diagram showing an EL spectrum of an organic EL device.
  • Figure 22 is a graph plotting the relationship between the current density and the external quantum efficiency of an organic EL device.
  • FIG. 23 is a schematic perspective view showing a case where the organic EL device according to the present invention is used for a passive matrix display.
  • FIG. 24 is a schematic perspective view showing a case where the organic EL device according to the present invention is used for an active matrix display.
  • organometallic complexes including platinum-based organometallic complexes, and evaluating their physical properties, it was found that organometallic complexes having N "C" N-type tridentate ligands were not dissolved in solution but in phosphorus.
  • the phosphorescent light-emitting solid When used as a light-emitting solid, it can emit a very strong phosphorescent light; this phosphorescent light-emitting solid can exhibit good vacuum deposition properties; Neat film consisting only of an organometallic complex having a nucleus ⁇ ⁇ ⁇ A doped film containing an organometallic complex having an NC-N-type tridentate ligand can be produced, and the produced film is uniformly flat and has good emission characteristics
  • the phosphorescent light-emitting solid according to the present invention has two nitrogen atoms and a space between the two nitrogen atoms. And a coordination bond to a central metal atom with one carbon atom that bonds to the two nitrogen atoms through a force, a bond, and one or more halogen atoms.
  • this organometallic complex Containing an organometallic complex.
  • this organometallic complex the two nitrogen atoms and carbon atoms that coordinate with the metal bond in the order of N, C, and N. That is, this organometallic complex has an N "C” N-type tridentate ligand. “—” Is a symbol indicating that a bond exists between N and C or between C and N.
  • Many of the tridentate ligands according to the present invention form substantially the same plane with the central metal M, but it goes without saying that other spatial arrangements can also be included in the scope of the present invention.
  • the phosphorescent solid according to the present invention may be composed solely of this organometallic complex.1 It may contain other components. And those in the form of a film. In the case of a film such as a light-emitting layer of an organic EL device, a neat film and a film in which an organometallic complex is contained as a guest or a host of the light-emitting layer are also included.
  • the phosphorescent solid according to the present invention is preferably a phosphorescent solid containing an organometallic complex having a structure represented by the following formula (1).
  • M represents a metal atom
  • X represents a halogen atom
  • Ar 1 , Ar 2 , and Ar 3 each independently represent a cyclic structure which may have a substituent
  • Ar 1 one a r 2 and a r 2 - binding of a r 3 is also a single bond, good also with a double bond Rere.
  • a double bond may be conjugated to another double bond.
  • M and Ar 1 and M and Ar 3 have an M—N coordination bond
  • M and Ar 2 have an M—C direct bond.
  • Substituents of Ar 1, Ar 2, A r 3 are each, Ar 1, Ar 2, A r 3 above and between each other A r 1 and A of each other and r 2 A r 2 and A r 3, They may be bonded to each other to form a ring structure.
  • M is a central metal atom of the organometallic complex according to the present invention.
  • Fe, Co, Ni, Ru, Rh, Pd, ⁇ s, Ir, Pt and the like can be mentioned. Among these, Pt is particularly preferred.
  • X represents a halogen atom, and examples thereof include F, C 1, Br, and I. It is preferable that the tridentate ligand and X are selected so that the stable coordination number of the central metal atom is satisfied and the complex as a whole is electrically neutral.
  • the cyclic structure preferably contains an aromatic ring. It may contain a condensed ring or a heterocyclic ring. Preferably, Ar 1 , Ar 2 and Ar 3 all contain an aromatic ring.
  • N "C" N the bond between N and C or the bond between C and N usually includes the case where another atom is interposed.
  • the bond of Ar 1 —Ar 2 and Ar 2 —Ar 3 in the above formula (1) corresponds to the case where another atom is interposed. Any other atom can be used as long as it is not contrary to the gist of the present invention, but carbon is preferred.
  • the bond between N and C and Z or C and N in the bond of N "C” N is preferably a bond through two carbon atoms.
  • the phosphorus according to the present invention is used as exemplified in Formula (4).
  • Light-emitting solid force Two nitrogen atoms and one carbon atom coordinate one or more of a tridentate ligand coordinated to the central metal atom and a halogen atom, and these two nitrogen atoms And an organometallic complex having a structural portion in which one carbon atom and a central metal atom are fused with two 5-membered rings sharing the bond between the carbon atom and the central metal atom. This structure makes it easier to obtain very strong phosphorescence.
  • the bond other than the bond between the ligand and the central metal atom may be a single bond or a double bond.
  • a double bond may be conjugated to another double bond.
  • the bonds other than the bond between the ligand and the central metal atom include the bond portion omitted in the formula (4). Specifically, the structure shown in FIG. 1 can be exemplified.
  • a r 1 to A r 3 are more preferably the combinations described below, and the molecular structure of the ligand More preferably, the symmetry of the structure is large.
  • the term “symmetry of the molecular structure of the ligand” means that A r 2 has a symmetric structure with respect to the bond axis of ⁇ —C, excluding or including the substituent, The relationship between 1 and Ar 3 is symmetrical about the bond axis of M—C, excluding or including the substituent, or satisfies both. If the symmetry of the molecular structure is large, it is considered that the phosphorescent light emission intensity of the complex is increased.
  • the structural portion having the shape in which the two 5-membered rings are condensed is a structural portion represented by the following formula (2), because the symmetry of the molecular structure is increased.
  • Equation (2) M and X are the same as in equation (1).
  • Y is, independently of one another, a carbon or nitrogen atom.
  • N-Y binding moiety form part of A r 1 or A r 3 in the formula (1), the benzene nucleus which constitutes a part of A r 2 may have a substituent .
  • the bond other than the bond between the ligand and the central metal atom may be a single bond or a double bond.
  • a double bond may be conjugated to another double bond. It goes without saying that bonds other than the bond between the ligand and the central metal atom include the bond portion omitted in the formula (2).
  • a r 1 and A r 3 independently of one another, it is also preferred to include a monocyclic or polycyclic aromatic ring. Also, it is preferable that A r 1 and A r 3 are the same. In this case, it is more preferable that the structural part having the shape in which the two five-membered rings are fused is a structural part represented by the following formula (3), since the symmetry of the molecular structure is further increased.
  • M and X are the same as those in the formula (1).
  • the benzene nuclei may have a substituent independently of each other, and the substituents may be in the same or adjacent ring. May be bonded to each other.
  • Ar 1 , Ar 2 and Ar 3 described above may be substituted at any position of the cyclic structure.
  • Ar 1 and Ar 3 the structure of FIG. 2 or its mirror image structure can be mentioned, and for Ar 2 , the structure of FIG. 3 can be mentioned.
  • Each symbol has the same meaning as the symbol in formula (1).
  • the structures of Ar 1 , Ar 2 , and Ar 3 are the parts enclosed in the middle of Figs.
  • ring hydrogen may be substituted with a substituent.
  • substituents of Ar 1, Ar 2, Ar 3 are each, Ar A r 2, A r 3 on a Rapi therebetween of A r 1 and A r 2 Contact and Ar 2 and Ar 3 between each other of And may be combined with each other to form a cyclic structure.
  • the organometallic complex according to the present invention may include a tridentate ligand, a central metal M and a plurality of halogen atoms X, as exemplified by a dimer or the like. And one having one halogen atom and one central metal atom. Advantages such as easy formation of a deposited film can be obtained.
  • the organometallic complex is electrically neutral or nearly neutral in a solid state. More preferably, it is neutral. This neutrality can be determined from the fact that the organometallic complex does not substantially have ionicity, does not have polarizability, or has low polarizability.
  • the phosphorescent solid according to the present invention preferably uses an organometallic complex having a purity of 99.5% by weight or more. This is because it becomes easier to obtain a phosphorescent solid that emits strong phosphorescence. More preferably, an organometallic complex having a purity of 99.8% by weight or more is used.
  • the purity of the organometallic complex means the concentration of the organic metal complex in the phosphorescent solid when the phosphorescent solid according to the present invention includes a plurality of components. Rather than the purity of the organometallic complex used to construct the phosphorescent solid.
  • One of the means to apply OLEDs to full-color displays is to prepare OLEDs for each color of red, green, and blue, and use a combination of these three as one element. I have. Since the phosphorescent light-emitting solid according to the present invention can adjust the emission color by changing the molecular structure of the tridentate ligand of the organometallic complex to be contained, such a plurality of emission colors is required. It can be suitably used as a light-emitting material or the like in an application for use. In particular, it can be suitably used for an organic EL device.
  • the phosphorescent solid according to the present invention is the solid of the organometallic complex according to the present invention and is in a state of barta before forming a film or the like is mainly described.
  • the phosphorescent solid according to the present invention includes a component other than the organometallic complex according to the present invention in a bulk state, and according to the present invention in a state after being formed in a film or the like.
  • the organic metal complex may be composed of the solid itself, or may contain components other than the organometallic complex according to the present invention after being formed into a film or the like, and thus belong to the scope of the present invention. ,.
  • the phosphorescent solid according to the present invention is preferably contained as a light-emitting material in an organic EL device, and may be contained in a light-emitting layer, or a light-emitting layer / electron transport layer, a light-emitting layer / hole transport layer, or the like. May be contained.
  • the light-emitting layer may be formed by forming a film with a phosphorescent light-emitting solid, or may be formed by including other materials.
  • the phosphorescent light-emitting solid used in the organic EL device of the present invention emits strong phosphorescence at room temperature, it should be used as a luminescent material contained in the color conversion layer in the case of a color conversion type organic EL device. Is also possible.
  • the phosphorescent solid according to the present invention can function as both a guest and a host. Also, it may be made to coexist with other host materials and guest materials. Other host materials that can coexist are low molecular weight materials and high molecular weight materials. A low molecular weight compound having a number average molecular weight of not more than 1,000 is preferable, and a high molecular weight compound having a number average molecular weight of not less than 200,000 is preferable. It is more preferable to use a material in which the first triplet excitation energy of the host material is higher than the first triplet excitation energy of the contained organometallic complex.
  • R 1 and R 2 each represent a substituent provided at an arbitrary position in the cyclic structure, and each independently represents a hydrogen atom, a halogen atom, an alkoxy group, an amino group, an alkyl group, a cycloalkyl group, or a nitrogen atom.
  • R 1 and R 2 each represent a substituent provided at an arbitrary position in the cyclic structure, and each independently represents a hydrogen atom, a halogen atom, an alkoxy group, an amino group, an alkyl group, a cycloalkyl group, or a nitrogen atom.
  • R 1 and R 2 may be bonded to each other, and may form an aromatic ring which may contain a nitrogen atom, a sulfur atom, and an oxygen atom, and these may be further substituted.
  • Ar represents a divalent or trivalent aromatic group or a heterocyclic aromatic group. Examples include groups as shown in FIG. A hydrogen atom in the ring structure may be substituted.
  • examples of the linking group R are shown in FIG.
  • the above canolebazole compound When the above canolebazole compound is mixed with the organometallic complex of the present invention, it has a small interaction with the complex and therefore has little effect on the intrinsic light emission characteristics of the complex, and is particularly effective as a host material.
  • the compound having the formula represented by this formula 4,4'-bis (9-model rubazolyl) -biphenyl (CBP) shown in FIG. 8 can be mentioned.
  • polyparaphenylene vinylene (PPV), polythiophene (PAT), polyparaphenylene (PPP), polyvinyl carbazole (PVC), and polyfluorene (PF) And polyacetylene (PA) derivatives are preferred.
  • a hydrogen atom in the ring structure may be substituted.
  • the organic EL device has a configuration in which a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, etc. are sandwiched between a positive electrode and a negative electrode. Of these, the hole injection layer, hole transport layer, electron transport layer, and electron injection layer may not exist. Including other layers Good. One layer can handle multiple functions.
  • FIG. 15 is a schematic side cross-sectional view of an organic EL device, showing a configuration without a color conversion layer, and FIG. 16 showing a configuration with a color conversion layer.
  • Fig. 15 shows the substrate 1, the positive electrode 2, the hole transport layer 3, the light emitting layer 4, the electron transport layer 5, and the negative electrode 6, and Fig. 16 shows the color conversion layer 16 1 in addition to these. Have been.
  • Positive electrode Z hole injection layer / hole transport layer and light emitting layer / electron transport layer / electron injection layer Z negative electrode Positive electrode Z hole injection layer Z hole transport layer / light emitting layer, electron transport layer,
  • each layer the thickness of each layer, and the manufacturing method are exemplified as follows.
  • the material of the positive electrode is not particularly limited and may be appropriately selected depending on the intended purpose.
  • Examples include metals, alloys, metal oxides, electrically conductive compounds, and mixtures thereof. Materials with a function of 4 eV or more are preferred.
  • the material for the positive electrode include conductive metal oxides such as tin oxide, zinc oxide, indium oxide, and indium tin oxide ( ⁇ ); gold, silver, chromium, nickel, and the like.
  • conductive metal oxides such as tin oxide, zinc oxide, indium oxide, and indium tin oxide ( ⁇ ); gold, silver, chromium, nickel, and the like.
  • conductive metal oxides are preferred, and ITO is particularly preferred from the viewpoints of productivity, high conductivity, transparency, and the like.
  • the thickness of the positive electrode is not particularly limited and can be appropriately selected depending on the material and the like, but is preferably 1 to 5000 nm, more preferably 20 to 200 nm.
  • the positive electrode is usually formed on a substrate such as glass such as soda lime glass and alkali-free glass, and transparent resin.
  • a substrate such as soda lime glass and alkali-free glass, and transparent resin.
  • alkali-free glass, silica, and soda-lime glass coated with a barrier coat are preferred from the viewpoint of reducing elution from the glass!
  • the thickness of the substrate is not particularly limited as long as the thickness is sufficient to maintain the mechanical strength.However, when glass is used as the base material, the thickness is usually 0.2 mm or more, and 0.7 mm or more. preferable.
  • the positive electrode for example, vapor deposition, wet film formation, electron beam, sputtering, reactive sputtering, MBE (molecular epitaxy), cluster ion beam, ion plating, and plasma polymerization (High frequency excitation ion plating method), molecular lamination method, printing method, transfer method, chemical reaction method (sol-gel method and the like), and a method of applying a dispersion such as ITO can be suitably formed.
  • the positive electrode can be washed or otherwise treated to lower the driving voltage of the organic EL element or increase the luminous efficiency.
  • a UV-ozone treatment, a plasma treatment and the like are preferably mentioned.
  • the material for the hole injection layer is not particularly limited and may be appropriately selected depending on the intended purpose.
  • the starburst amine (4, 4 ', 4 "tris [3—methylpheny 1 (; henyl) am ino] tripheny l amine, m—MTDATA), copper phthalocyanine, polya Phosphorus and the like are preferred.
  • the thickness of the hole injection layer is not particularly limited and can be appropriately selected depending on the purpose.
  • the thickness is preferably about 1 to 100 nm, and more preferably 5 to 500 nm.
  • the hole injection layer is formed by, for example, vapor deposition, wet film formation, electron beam, sputtering, reactive sputtering, MBE, cluster ion beam, ion plating, plasma polymerization (high frequency excitation). It can be suitably formed by an ion plating method, a molecular lamination method, an LB method, a printing method, a transfer method, or the like.
  • the material of the hole transport layer is not particularly limited and can be appropriately selected depending on the purpose.
  • aromatic amine compounds canolebazole, imidazole, triazole, oxazole, oxazole, polyarylalkane, pyrazoline, Pyrazolone, phenylenediamine, arylamine, amino-protected norecon, stylinoleanthracene, fuenoresenone, hydrazone, stinoleben, silazane, styrylamine, aromatic dimethylene Vden compound, porphyrin-based compound, polysilane-based compound, poly (N- -Vinylcarbazole), aniline-based copolymers, thiophene oligomers and polymers, conductive polymer oligomers and polymers such as polythiophene, and carbon films.
  • a hole transport layer and a light emitting layer can be formed.
  • aromatic amine compounds are preferred. Specifically, N, N'-diphenyl-N, N'-bis (3-methylpheninole) -1 [1,1'-bipheninole] -14,4'diamine (TPD) and Aromatic amines such as NPD are more preferred.
  • the thickness of the hole transport layer is not particularly limited and may be appropriately selected depending on the purpose.
  • the thickness is usually 1 to 500 nm, and preferably 5 to 100 nm.
  • the same method as in the case of the hole injection layer can be used by appropriately changing the raw materials and conditions.
  • the material of the electron transport layer is not particularly limited, and may be appropriately selected according to the purpose.
  • a hydroxyquinoline metal complex such as tris (8-quinolinolato) alminium (A1q), an anolemminium hydroxyquinoline-biphenylinoleoxy complex (BA 1q) and other hydroxyquinoline aryl / reoxy complexes, oxadiazole compounds, triazole compounds, phenanthone phosphorus compounds, perylene compounds, pyridine compounds, pyrimidine compounds, quinoxaline compounds, diphenylinolequinone compounds, di-substituted fluorene compounds, etc.
  • A1q 8-quinolinolato alminium
  • BA 1q anolemminium hydroxyquinoline-biphenylinoleoxy complex
  • other hydroxyquinoline aryl / reoxy complexes oxadiazole compounds
  • triazole compounds phenanthone phosphorus compounds
  • a light emitting layer and an electron transport layer can be formed.
  • the hole transport layer is also mixed to form a film, the hole is formed.
  • a transport layer, a light emitting layer, and an electron transport layer can be formed.
  • the thickness of the electron transporting layer is not particularly limited and can be appropriately selected depending on the purpose.
  • the thickness is usually about 1 to 500 nm, and preferably 10 to 50 nm.
  • the electron transport layer may be composed of two or more layers.
  • the light emitting region in the device can be limited to the light emitting layer. It is preferable because unnecessary light emission from the electron transport layer can be prevented.
  • Such a material having a light absorption edge having a shorter wavelength than the phosphorescent solid according to the present invention such as a hydroxyquinoline-aryloxy complex, a phenanthroline compound, an oxadiazole compound, a triazole compound, and 8-quinolinol.
  • An organometallic complex having the compound as a ligand can be given.
  • the compounds represented by B A1q and FIG. 13 are preferable.
  • three branches having no chemical group at the tip means a t-tert-butyl group.
  • the same method as in the case of the hole injecting layer can be used by appropriately changing the raw materials and conditions.
  • the material for the electron injection layer is not particularly limited and can be appropriately selected depending on the intended purpose. Examples thereof include alkali metal fluorides such as lithium fluoride, and alkaline earth metal fluorides such as sodium fluoride fluoride. And the like can be suitably used. Electron injection layer
  • the thickness is not particularly limited and can be appropriately selected depending on the purpose. For example, the thickness is usually about 0.1 to 10 nm, and preferably 0.5 to 211 m.
  • the electron injection layer can be suitably formed by, for example, an evaporation method, an electron beam method, a sputtering method, or the like.
  • the material of the negative electrode is not particularly limited, and can be appropriately selected according to the adhesion between the layer and molecules adjacent to the negative electrode such as the electron transport layer and the light emitting layer, ionization potential, stability, and the like. Examples thereof include metals, alloys, metal oxides, electrically conductive compounds, and mixtures thereof.
  • the negative electrode material include alkali metals (eg, Li, Na, K, Cs, etc.), alkaline earth metals (eg, Mg, Ca, etc.), gold, silver, lead, and aluminum.
  • a material having a work function of 4 eV or less is preferable, and aluminum, a lithium-aluminum alloy or a mixed metal thereof, a magnesium-silver alloy or a mixed metal thereof are more preferable.
  • the thickness of the negative electrode is not particularly limited and may be appropriately selected depending on the material of the negative electrode, but is preferably 1 to: L0000nm, more preferably 20 to 200im. Better.
  • the negative electrode for example, evaporation method, wet film forming method, electron beam method, sputtering method, reactive sputtering method, MBE method, cluster ion beam method, ion plating method, plasma polymerization method (high frequency excitation ion plating method) It can be suitably formed by a printing method, a transfer method, or the like.
  • two or more materials When two or more materials are used in combination as a negative electrode material, two or more materials may be simultaneously evaporated to form an alloy electrode or the like, or an alloy electrode or the like may be formed by evaporating a previously prepared alloy. Is also good.
  • the organic EL device of the present invention may have other layers appropriately selected according to the purpose.
  • a hole blocking layer and a protective layer are preferably exemplified.
  • the hole blocking layer is disposed between the light emitting layer and the electron transport layer. If the organic EL device has a hole blocking layer, holes transported from the positive electrode are blocked by the hole blocking layer, and electrons transported from the negative electrode pass through the hole blocking layer. As a result, the electrons and holes recombine efficiently in the light emitting layer. For this reason, recombination of holes and electrons in the organic thin film layer other than the light emitting layer can be prevented, and light emission of the target luminescent dye can be efficiently obtained, which is advantageous in terms of color purity and the like.
  • the material of the hole blocking layer is not particularly limited, and can be appropriately selected from the same materials as those of the electron transporting layer according to the purpose.
  • the thickness of the hole blocking layer is not particularly limited and may be appropriately selected depending on the purpose.
  • the thickness is usually about 1 to 50 nm, preferably 5 to 50 nm.
  • the hole blocking layer may have a single-layer structure or a multilayer structure.
  • the hole blocking layer is formed, for example, by a vapor deposition method, a wet film formation method, an electron beam method, a sputtering method, a reactive sputtering method, a ⁇ method, a cluster ion beam method, an ion plating method, a plasma polymerization method (a high-frequency excitation ion plating method).
  • Printing method a molecular lamination method, an LB method, a printing method, a transfer method, and the like.
  • the protective layer is a layer that protects the organic EL element from the influence of the outside world, and is formed so as to wrap around the above-described laminated structure.
  • the material of the protective layer is not particularly limited, and can be appropriately selected according to the purpose.For example, molecules or substances such as moisture and oxygen that accelerate the deterioration of the organic EL element enter the organic EL element. Things that can be deterred are preferred! /.
  • the protective layer is formed, for example, by a vapor deposition method, a wet film forming method, a sputtering method, a reactive sputtering method, a MBE method, a cluster ion beam method, an ion plating method, a plasma polymerization method (high frequency excitation ion plating method), and printing. It can be more suitably formed by a method or a transfer method.
  • the organic EL device of the present invention may have a color conversion layer appropriately selected according to the purpose, and the color conversion layer may contain the phosphorescent solid of the present invention.
  • the color conversion layer is a layer that absorbs light emitted from an organic EL device and emits light by changing the wavelength, for example, as described in Japanese Patent Application Laid-Open No. 3-152927. It is produced between the substrate on the light extraction side of the EL element and the IT ⁇ electrode and converts blue into green or red and emits it, enabling multicolor display devices.
  • the color conversion layer may be of any thickness, material, and manufacturing method as long as it can sufficiently absorb the light to be converted and can convert the light into a desired wavelength. It preferably has a thickness of 100 to 100 jum, more preferably 1 to 50 ⁇ , and is manufactured by photolithography or the like.
  • a force that can be formed according to a known method for example, a vapor deposition method such as vacuum deposition, a wet film forming method, an MBE method, a cluster ion beam method, a molecular lamination method, It can be suitably formed by an LB method, a printing method, a transfer method, or the like.
  • the vapor deposition method is preferable because it can be easily and efficiently manufactured at low cost without the problem of waste liquid treatment without using an organic solvent.
  • the light emitting layer is designed to have a single layer structure, For example, when the light emitting layer is formed as a hole transporting layer, a light emitting layer and an electron transporting layer, a wet film forming method is also preferable.
  • the vapor deposition method is not particularly limited and may be appropriately selected from known methods according to the purpose. Examples thereof include a vacuum deposition method, a resistance heating deposition method, a chemical vapor deposition method, and a physical vapor deposition method. Examples of the chemical vapor deposition method include a plasma CVD method, a laser CVD method, a thermal CVD method, and a gas source CVD method.
  • a binder composed of a host and / or a polymer and a phosphorescent solid according to the present invention are mixed in a solvent, and then spin coating, ink jetting, dip coating, blade coating are performed. It is also possible to apply by a wet film forming method such as a coating method.
  • the light emitting layer has By having the function of an electron transport layer, it is also possible to configure a single layer as a hole transport layer / light emitting layer or a light emitting layer / electron transport layer / a hole transport layer / light emitting layer / electron transport layer.
  • examples of binders that can be used include polyvinyl carbazolone, polycarbonate, polyvinyl chloride, polystyrene, polymethyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, and ketone resin.
  • examples include phenoxy resin, polyamide, ethyl cellulose, vinyl acetate, ABS resin, polyurethane, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, and silicone resin.
  • a panel using the three-color light-emitting method requires an organic EL element portion that emits three colors of red, green, and blue, respectively.
  • the following light-emitting element portions can be exemplified as the respective color light-emitting element portions.
  • the organic EL display using the organic EL element according to the present invention is expected to have high luminous efficiency, long drive life, and stable driving.
  • This organic EL device can be used as a passive matrix panel or an active matrix panel (for example, Nikkei Electronics, March 13, 2000, No. 765, pp. 55-62).
  • An organic EL device according to the present invention is described in US Pat.
  • Fig. 23 shows the case when used for a passive matrix display.
  • FIG. 23 shows a configuration example of the positive electrode / hole transport layer / light emitting layer / electron transport layer Z negative electrode. In FIG.
  • a positive electrode 2 made of IT, a hole transport layer 3, a light emitting layer 4, an electron transport layer 5, and a negative electrode 6 made of metal are laminated on a glass substrate 1.
  • the positive electrode 2 made of ITO is the row electrode
  • the negative electrode 6 made of metal is the column electrode.
  • red light emission 7, green light emission 8, and blue light emission 9 are realized by changing the light emitting layer forming material used for the light emitting layer 4.
  • FIG. 24 shows a case where the organic EL device according to the present invention is used for an active matrix display.
  • FIG. 24 also shows a configuration example of the positive electrode Z, the hole transport layer Z, the light emitting layer / the electron transport layer Z, and the negative electrode.
  • the organic EL element is composed of a driving circuit 21, a TFT (Thin Film Transistor) circuit 22, a positive electrode 2 composed of ITO, a hole transport layer 3, a light emitting layer 4, An electron transport layer 5 and a negative electrode 6 made of metal are laminated. Also in this figure, by changing the light emitting layer forming material used for the light emitting layer 4, red light emission 7, green light emission 8, and blue light emission 9 are realized.
  • the tridentate ligands used in the examples of the present invention were synthesized by the Sti 11 e coupling method in the literature Organome tallics (D. J. Cardenas and AM E chavarren, Vol. 18, p. 3337 (1999). Year)). These ligands are based on the Suzuki force pulling method (references: MD S in dkh e dk ar, HR Mu 11 a, MA Wurth and A. C ammers—Go dw in, T e 1 & 116 (011, Vol. 57, Vol.
  • the tridentate ligand (3,5-di (2-pyridyl) pyridine (3,5-di (2-pyridyl) pyridin, hereinafter abbreviated as dppr) is 3,5-dibromotoluene and 3,5-dibromotoluene.
  • the synthesis was performed in the same manner as in Synthesis Example 1 except that pyridine was replaced with the same procedure as in Synthesis Example 1 except that the ligand was changed from dpt to dppr.
  • An organic metal complex, Pt (dppr) CI was synthesized, and the yield was 14%.
  • a thin film doped with 2% by weight of Pt (dpt) ⁇ 1 synthesized in Synthesis Example 1 to ⁇ 8? was produced by co-evaporation.
  • the thickness was 50 nm.
  • a single film of A1q with a known fluorescence quantum yield was prepared by evaporation and used as a reference.
  • the phosphorescence quantum yield of the phosphorescent solid (thin film) of the present invention was determined by setting the fluorescence quantum yield of the reference A1q thin film to 22%. The measurement was performed as follows. That is, in the apparatus shown in FIG. 19, a 365-nm steady light 1911 is used as the excitation light, and the amount of transmission and reflection of the excitation light in the sample 196 is determined by the photodiode 1 via the mirrors 194 and 195.
  • the emission spectrum of the sample thin film was measured with a spectral radiance meter 1933 (CS-1000 manufactured by Minolta) while monitoring with 92 (a photosensor C2719 manufactured by Hamamatsu Photonitas).
  • the phosphorescence quantum yield was calculated by comparing the emission intensity per unit absorption of the excitation light with the value of a thin film of a known compound (Alq). Table 1 shows the results. [Example 2]
  • the phosphorescent quantum yield was measured under the same conditions as in Example 1 except that the light emitting material was changed to Pt (dqt) C1. The results are shown in Table 1.
  • the phosphorescence quantum yield was measured under the same conditions as in Example 1 except that the luminescent material was changed to Pt (dppr) CI. The results are shown in Table 1.
  • the phosphorescent thin film of the present invention has a very high phosphorescence quantum yield.
  • the Pt (dpt) C 1 complex reported by JAG Wi 11 iams et al. In Iii org. Chem. (Vol. 42, p. 8609—8611, 2003)
  • the phosphorescence quantum yield was 68% in the solution state, but surprisingly, the solid state could significantly improve the phosphorescence quantum yield to 98%.
  • Comparative Examples 1 to 3 are three N “N” C types described in Japanese Patent Application Laid-Open No. 2002-3653552.
  • This figure shows the phosphorescence quantum yield of an organometallic complex having a ligand in a dichloromethane solution state.
  • the molecular structure of the organometallic complex having these three N—N ′′ C-type ligands is shown in FIG. 20. From this comparison, the organometallic complex having the N—C ′′ N-type ligand of the present invention is also shown. It can be understood that the phosphorescent light-emitting solid (thin film) using GaN has a very high phosphorescence quantum yield.
  • a stacked organic EL device was manufactured using the Pt (dpt) C1 complex for the light emitting layer as follows.
  • the layer doped with 2% by weight is 30 nm
  • the BCP is 20 nm as the hole blocking layer
  • the A1q is 20 nm as the electron transport layer
  • the LiF is 0 nm as the electron injection layer.
  • Each layer was deposited to a thickness of 511 m, and aluminum was deposited to a thickness of 100 nm and sealed in a nitrogen atmosphere.
  • IT ⁇ positive electrode
  • the aluminum electrode as the negative electrode
  • a voltage of 4 Green emission was observed above V.
  • Table 2 shows the emission peak wavelength, current efficiency, power efficiency, and external quantum efficiency when applying 5 V to the devices in Examples 4 to 9 and Comparative Example.
  • the external quantum efficiency is the ratio of the phosphorescent output to the input energy It represents the rate. Current efficiency, power efficiency, external quantum efficiency, the input current indicates a value of 0. ImAZcm 2.
  • An organic EL device was manufactured under the same conditions as in Example 4 except that the light emitting material was changed to Pt (dqt) CI.
  • the light emitting material was changed to Pt (dqt) CI.
  • An organic EL device was produced under the same conditions as in Example 4 except that the light emitting material was changed to Pt (dppr) CI.
  • Pt (dppr) CI When a voltage was applied with the ITO as the positive electrode and the aluminum electrode as the negative electrode, blue-green light emission was observed at a voltage of 4 V or more.
  • a polymer organic EL device was manufactured using the Pt (dpt) C1 complex for the light emitting layer as follows.
  • the glass substrate with the ITO electrode was washed with water, acetone, and isopropyl alcohol.
  • PEDOT PSS (poly (ethylenedioxythiophene): poly (styrenesulfonate)) thin film (50 nm thick) was prepared as a hole injection layer by spin coating, and was heated and dried at 200 ° C for 2 hours. did.
  • An organic EL device was manufactured under the same conditions as in Example 7 except that the light emitting material was changed to Pt (dqt) CI.
  • the light emitting material was changed to Pt (dqt) CI.
  • An organic EL device was manufactured under the same conditions as in Example 7 except that the light emitting material was changed to Pt (dppr) CI.
  • the light emitting material was changed to Pt (dppr) CI.
  • an organic EL device having high luminous efficiency and a high-performance organic EL device can be provided.

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Abstract

Un solide émetteur de phosphorescence composé d'un complexe organométallique possédant un liant ligand se coordonnant à un métal central via deux atomes d'azote et un atome de carbone se positionnant entre les deux atomes d'azote cités et se liant avec les deux atomes d'azote via des liaisons ; il possède un atome d'halogène agissant comme liant ; un élément luminescent utilisant le solide ; un dispositif EL organique utilisant l'élément. Le solide émetteur de phosphorescence peut émettre une phosphorescence ayant une très forte intensité dans un état solide ; ainsi, l'utilisation du solide dans un élément EL organique permet d'améliorer considérablement l'efficacité lumineuse, ce qui entraîne la réduction de la consommation électrique dans un dispositif EL organique.
PCT/JP2004/004485 2004-03-30 2004-03-30 Solide émettant une phosphorescence, élément électroluminescent organique et dispositif d'électroluminescence organique Ceased WO2005103195A1 (fr)

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US8389725B2 (en) 2008-02-29 2013-03-05 Arizona Board Of Regents For And On Behalf Of Arizona State University Tridentate platinum (II) complexes
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US9865825B2 (en) 2014-11-10 2018-01-09 Arizona Board Of Regents On Behalf Of Arizona State University Emitters based on octahedral metal complexes
US10056567B2 (en) 2014-02-28 2018-08-21 Arizona Board Of Regents On Behalf Of Arizona State University Chiral metal complexes as emitters for organic polarized electroluminescent devices
US10790457B2 (en) 2014-07-29 2020-09-29 Arizona Board Of Regents On Behalf Of Arizona State University Metal-assisted delayed fluorescent emitters containing tridentate ligands

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Cited By (18)

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US8106199B2 (en) 2007-02-13 2012-01-31 Arizona Board Of Regents For And On Behalf Of Arizona State University Organometallic materials for optical emission, optical absorption, and devices including organometallic materials
US8846940B2 (en) 2007-12-21 2014-09-30 Arizona Board Of Regents For And On Behalf Of Arizona State University Platinum (II) di (2-pyrazolyl) benzene chloride analogs and uses
US9082989B2 (en) 2007-12-21 2015-07-14 Arizona Board of Regents for and on behalf of Arizona State Univesity Platinum (II) di (2-pyrazolyl) benzene chloride analogs and uses
US8389725B2 (en) 2008-02-29 2013-03-05 Arizona Board Of Regents For And On Behalf Of Arizona State University Tridentate platinum (II) complexes
US8669364B2 (en) 2008-02-29 2014-03-11 Arizona Board Of Regents For And On Behalf Of Arizona State University Tridentate platinum (II) complexes
US9076974B2 (en) 2008-02-29 2015-07-07 Arizona Board Of Regents For And On Behalf Of Arizona State University Tridentate platinum (II) complexes
US9203039B2 (en) 2008-02-29 2015-12-01 Arizona Board Of Regents For And On Behalf Of Arizona State University Tridentate platinum (II) complexes
US10056567B2 (en) 2014-02-28 2018-08-21 Arizona Board Of Regents On Behalf Of Arizona State University Chiral metal complexes as emitters for organic polarized electroluminescent devices
US9502671B2 (en) 2014-07-28 2016-11-22 Arizona Board Of Regents On Behalf Of Arizona State University Tridentate cyclometalated metal complexes with six-membered coordination rings
US10964897B2 (en) 2014-07-28 2021-03-30 Arizona Board Of Regents On Behalf Of Arizona State University Tridentate cyclometalated metal complexes with six-membered coordination rings
US9985224B2 (en) 2014-07-28 2018-05-29 Arizona Board Of Regents On Behalf Of Arizona State University Tridentate cyclometalated metal complexes with six-membered coordination rings
US10411202B2 (en) 2014-07-28 2019-09-10 Arizon Board Of Regents On Behalf Of Arizona State University Tridentate cyclometalated metal complexes with six-membered coordination rings
US10790457B2 (en) 2014-07-29 2020-09-29 Arizona Board Of Regents On Behalf Of Arizona State University Metal-assisted delayed fluorescent emitters containing tridentate ligands
US11145830B2 (en) 2014-07-29 2021-10-12 Arizona Board Of Regents On Behalf Of Arizona State University Metal-assisted delayed fluorescent emitters containing tridentate ligands
US12082488B2 (en) 2014-07-29 2024-09-03 Arizona Board Of Regents On Behalf Of Arizona State University Metal-assisted delayed fluorescent emitters containing tridentate ligands
US9865825B2 (en) 2014-11-10 2018-01-09 Arizona Board Of Regents On Behalf Of Arizona State University Emitters based on octahedral metal complexes
US10991897B2 (en) 2014-11-10 2021-04-27 Arizona Board Of Regents On Behalf Of Arizona State University Emitters based on octahedral metal complexes
US11856840B2 (en) 2014-11-10 2023-12-26 Arizona Board Of Regents On Behalf Of Arizona State University Emitters based on octahedral metal complexes

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