Composition and organic light emitting device comprising the same
By using platinum (Pt)-containing organometallic compounds in combination with compounds with specific HOMO energy level differences in organic light-emitting devices, the problem of insufficient hole and electron transport efficiency was solved, the external quantum luminescence efficiency and lifetime of the device were improved, and the driving voltage was reduced.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- SAMSUNG DISPLAY CO LTD
- Filing Date
- 2020-06-30
- Publication Date
- 2026-07-03
AI Technical Summary
Existing organic light-emitting devices have shortcomings in the transport and recombination efficiency of holes and electrons, which affect the performance of the devices, especially in terms of external quantum luminescence efficiency, driving voltage and lifetime.
A combination of platinum (Pt)-containing organometallic compounds, a first compound, and a second and third compound is used to ensure that the difference in the highest occupied molecular orbital (HOMO) energy levels is between 0.01 eV and 0.30 eV. This is measured by photoelectron spectroscopy to promote hole transfer and maintain the positive polaron density. The composition does not contain iridium (Ir) to form the emitting layer of an organic light-emitting device.
This improved the external quantum luminescence efficiency of organic light-emitting devices, reduced the driving voltage, and enhanced the device's lifetime characteristics.
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Figure CN112186126B_ABST
Abstract
Description
[0001] Cross-reference to related applications
[0002] This application claims priority and benefits, and all benefits arising therefrom, to Korean Patent Application No. 10-2019-0078954 filed with the Korean Intellectual Property Office on July 1, 2019, the entire contents of which are incorporated herein by reference. Technical Field
[0003] One or more embodiments relate to compositions and organic light-emitting devices including the same. Background Technology
[0004] Organic light-emitting devices are self-emitting devices that have better characteristics in terms of viewing angle, response time, brightness, driving voltage, and response speed, and produce full-color images.
[0005] In this example, the organic light-emitting device includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer includes an emitting layer. A hole transport region is located between the anode and the emitting layer, and an electron transport region is located between the emitting layer and the cathode. Holes supplied from the anode can move towards the emitting layer through the hole transport region, and electrons supplied from the cathode can move towards the emitting layer through the electron transport region. Holes and electrons recombine in the emitting layer to generate excitons. These excitons transition from an excited state to the ground state, thereby producing light. Summary of the Invention
[0006] One or more embodiments relate to novel compositions and organic light-emitting devices including the same.
[0007] Additional aspects will be set forth in part in the following description, and in part will be apparent from the description, or may be learned through practice of the provided embodiments.
[0008] One aspect of this disclosure provides a composition comprising:
[0009] Organometallic compounds containing platinum (Pt), compound one, compound two, and compound three.
[0010] The composition described herein does not include iridium (Ir).
[0011] The Pt-containing organometallic compounds, compound one, compound two, and compound three are different from each other.
[0012] The first compound includes at least one electron transport component.
[0013] The second and third compounds do not contain metals.
[0014] The absolute values of the highest occupied molecular orbital (HOMO) energy levels of the second compound and the third compound are respectively 5.30 eV to 5.85 eV.
[0015] The absolute value of the HOMO energy level of the second compound differs from that of the third compound by 0.01 eV to 0.30 eV, and
[0016] The HOMO levels of the second and third compounds were measured in air using a photoelectron spectrometer.
[0017] Another aspect of this disclosure provides an organic light-emitting device, including:
[0018] A first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes the composition. Attached Figure Description
[0019] These and / or other aspects will become clearer and more readily understood from the following description of embodiments considered in conjunction with the accompanying drawings. Figure 1 This is a schematic diagram of an organic light-emitting device according to an embodiment. Detailed Implementation
[0020] The embodiments will now be described in detail, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals always refer to the same elements. In this respect, the embodiments may take different forms and should not be construed as limited to the description set forth herein. Therefore, the embodiments are described below only with reference to the accompanying drawings to illustrate aspects of this description. As used herein, the term "and / or" includes any and all combinations of one or more of the associated enumerated items. Expressions such as "at least one of" modify the entire list of elements when preceding or following it, without modifying any individual element of the list.
[0021] It will be understood that when an element is referred to as being "on" another element, it may be directly on said other element or there may be intermediate elements therein. Conversely, when an element is referred to as being "directly on" another element, there are no intermediate elements.
[0022] It will be understood that although the terms “first,” “second,” “third,” etc., may be used herein to describe various elements, components, regions, layers, and / or portions, these elements, components, regions, layers, and / or portions should not be limited by these terms. These terms are used only to distinguish one element, component, region, layer, or portion from another. Therefore, without departing from the teachings of this embodiment, the “first element,” “component,” “region,” “layer,” or “portion” discussed below may be referred to as a second element, component, region, layer, or portion.
[0023] The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting. As used herein, “a,” “the,” and “at least one” do not indicate a limitation of quantity but are intended to cover both the singular and the plural unless the context clearly indicates otherwise. For example, unless the context clearly indicates otherwise, “(a) element” has the same meaning as “at least one element.”
[0024] The term “or” means “and / or”. As used herein, the term “and / or” includes any and all combinations of one or more of the related listed items. It will be further understood that the terms “comprising” or “including” as used in this specification indicate the presence of the stated features, areas, integrals, steps, operations, elements, and / or components, but do not preclude the presence or addition of one or more additional features, areas, integrals, steps, operations, elements, components, and / or collections thereof.
[0025] Furthermore, relative terms, such as “lower” or “bottom” and “upper” or “top”, may be used herein to describe the relationship of one element to another element as shown in the figures. It will be understood that, in addition to the orientation depicted in the figures, relative terms are intended to cover different orientations of the device. For example, if the device in one of the figures is flipped, an element described as being “lower” to another element will be oriented to be “upper” to the other element. Thus, depending on the specific orientation of the figure, the exemplary term “lower” may encompass both “lower” and “upper” orientations. Similarly, if the device in one of the figures is flipped, an element described as being “below” or “under” another element will be oriented “above” the other element. Thus, the exemplary terms “below” or “under” may include both “above” and “below” orientations.
[0026] As used herein, “about” or “approximately” includes the stated value and means within an acceptable range of deviation from the specific value, as determined by a person skilled in the art taking into account the measurement in question and the errors associated with the measurement of the specific quantity (i.e., limitations of the measurement system). For example, “about” may mean a deviation from the stated value within one or more standard deviations, or within ±30%, 20%, 10%, or 5%.
[0027] Unless otherwise defined, all terms used herein (including technical and scientific terms) have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure pertains. It will be further understood that terms, such as those defined in common dictionaries, should be interpreted as having the same meaning as they have in the context of this disclosure and the relevant field, and will not be interpreted in an idealized or overly formal sense unless clearly defined herein.
[0028] Exemplary embodiments are described herein with reference to cross-sectional views that serve as schematic representations of idealized embodiments. Thus, deviations from the shapes depicted in the figures will be expected as a result of, for example, manufacturing techniques and / or tolerances. Therefore, the embodiments described herein should not be construed as limited to the specific shapes of the regions illustrated herein, but rather include, for example, deviations in shape due to manufacturing processes. For example, regions illustrated or described as flat may typically have rough and / or non-linear characteristics. Furthermore, sharp corners in the figures may be rounded. Therefore, the regions illustrated in the figures are schematic in nature, and their shapes are not intended to illustrate the precise shapes of the regions, nor are they intended to limit the scope of the claims.
[0029] Compositions according to one aspect of this disclosure may include platinum (Pt)-containing organometallic compounds, a first compound, a second compound, and a third compound. The Pt-containing organometallic compounds, the first compound, the second compound, and the third compound will be described in detail below.
[0030] The composition may be free of iridium (Ir).
[0031] The Pt-containing organometallic compound, the first compound, the second compound, and the third compound included in the composition may be different from each other. That is, the composition may include four or more different compounds.
[0032] In one or more embodiments, the Pt-containing organometallic compound may include Pt and an organic ligand, and the Pt and the organic ligand may form one, two, three or four rings with metallization.
[0033] In one or more embodiments, the Pt-containing organometallic compound may include Pt and a tetradentate organic ligand, and the Pt and the tetradentate organic ligand may form 3 or 4 rings with metallization.
[0034] In one or more embodiments, the Pt-containing organometallic compound may include Pt and a tetradentate organic ligand, and the tetradentate organic ligand may include a benzimidazole group and a pyridine group. The benzimidazole group and the pyridine group may each be directly attached to the Pt in the Pt-containing organometallic compound.
[0035] The absolute values of the highest occupied molecular orbital (HOMO) energy levels of Pt-containing organometallic compounds can range from 5.25 eV to 5.55 eV.
[0036] The first compound may include at least one electron transport component.
[0037] In this specification, the term "electron transport portion" may be cyano, fluorine, a nitrogen-containing cyclic group lacking π electrons, a group represented by one of the following formulas, or any combination thereof:
[0038]
[0039] In the above formula, *, *', and *" each represent a binding site with an adjacent atom.
[0040] Both the second and third compounds may not contain metals.
[0041] For example, the absolute values of the HOMO energy levels of the second compound and the third compound can each be from 5.30 eV to 5.85 eV, such as from 5.50 eV to 5.75 eV.
[0042] The absolute difference between the HOMO energy levels of the second and third compounds can be 0.01 eV to 0.30 eV, for example, 0.05 eV to 0.10 eV. When the absolute difference between the HOMO energy levels of the second and third compounds is within the above range, the effective HOMO energy disorder portion of the Gaussian disorder model (GDM) increases to facilitate hole transfer between the Pt-containing organometallic compound, the second compound, and the third compound, and the positive polaron density of the Pt-containing organometallic compound can be maintained at a high level. Therefore, electronic devices including this composition, such as organic light-emitting devices, can have high external quantum luminescence efficiency, low driving voltage, and high lifetime characteristics.
[0043] In one or more embodiments, at least one of the second and third compounds (e.g., all of the second and third compounds) may not include an electron transport portion.
[0044] In one or more embodiments, the first compound may include at least one π-electron-rich C3-C 30The compound contains a cyclic group and at least one electron transport moiety, and at least one of the second and third compounds (e.g., all of the second and third compounds) may each independently include at least one π-electron-rich C3-C group. 30 Cyclic groups and may not include electron transport components.
[0045] In one or more embodiments, at least one of the second and third compounds (e.g., all of the second and third compounds) may each be independently:
[0046] i) Fused rings, wherein one or more fifth rings and one or more sixth rings are fused together.
[0047] ii) by The group represented, or
[0048] iii) Any combination thereof,
[0049] The fifth ring can be a cyclopentadienyl group, a pyrrole group, a furan group, a thiophene group, or a thiorrole group.
[0050] The sixth ring can be a π-electron-rich C3-C 30 Cyclic groups, and
[0051] *, *', and *" each represent a binding site with an adjacent atom.
[0052] In this specification, the HOMO energy levels of the Pt-containing organometallic compounds, the first compound, the second compound, and the third compound can be measured in air using a photoelectron spectrometer (e.g., an AC3 manufactured by RIKEN KEIKI Co., Ltd.).
[0053] In one or more embodiments, the Pt-containing organometallic compound may be an organometallic compound represented by Formula 1, and / or
[0054] The first compound may be a compound represented by formula 2, and / or
[0055] The second and third compounds can each be independently represented by one of formulas 3-1 to 3-4:
[0056] Formula 1
[0057]
[0058] Formula 2
[0059]
[0060] Equation 3-1
[0061]
[0062] Equation 3-2
[0063]
[0064] Equation 3-3
[0065]
[0066] Equation 3-4
[0067]
[0068] In Equation 1, M can be Pt.
[0069] In Equation 1, Y1 to Y4 can each independently be a chemical bond (e.g., a covalent bond or a coordinate bond), O, S, N (R a ), C(R a (R) b ) or Si(R a (R) b When Y1 is a chemical bond, X1 can directly bond with M; when Y2 is a chemical bond, X2 can directly bond with M; when Y3 is a chemical bond, X3 can directly bond with M; and when Y4 is a chemical bond, X4 can directly bond with M.
[0070] For example, in Formula 1, Y1 can be O or S, and Y2 to Y4 can be chemical bonds.
[0071] In Equation 1, X1 to X4 can each be C or N independently.
[0072] In one or more embodiments, in Formula 1, Y1 may be O or S, Y2 to Y4 may each be a chemical bond, X1 and X3 may each be C, and X2 and X4 may each be N independently, but the embodiments of this disclosure are not limited thereto.
[0073] In Equation 1, two of the bonds between M and Y or X1, M and Y2 or X2, M and Y3 or X3, and M and Y4 or X4 can be coordinate bonds, and the other two bonds can each be covalent bonds. Therefore, the organometallic compound represented by Equation 1 can be electrically neutral.
[0074] For example, Y1 may not be a chemical bond. Y2 to Y4 may each be a chemical bond. The bond between Y1 and M, and the bond between X3 and M, may be covalent bonds. The bond between X2 and M, and the bond between X4 and M, may be coordinate bonds.
[0075] In Equation 1, rings CY1 to CY4 can each be independently C5-C. 30 Carbocyclic groups or C1-C 30 Heterocyclic groups.
[0076] In one or more embodiments, in Formula 1, rings CY1 to CY4 can each independently be: i) a first ring, ii) a second ring, iii) a fused ring in which two or more first rings are fused together, iv) a fused ring in which two or more second rings are fused together, or v) a fused ring in which one or more first rings are fused with one or more second rings, wherein
[0077] The first ring can be a cyclohexyl group, cyclohexene group, adamantyl group, norbornel group, norbornene group, phenyl group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, or triazine group, and
[0078] The second ring can be a cyclopentyl group, a cyclopentene group, a cyclopentadienyl group, a furan group, a thiophene group, a thiophene group, a pyrrole group, a pyrazole group, an imidazole group, or a triazole group. azole group, iso- azole group, thiazole group, isothiazole group, azathiophene group, Diazole group or thiadiazole group.
[0079] In one or more embodiments, in Formula 1, cyclo(CY1) to cyclo(CY4) can each independently be a cyclopentene group, a cyclohexyl group, a cyclohexene group, a phenyl group, a naphthyl group, an anthracene group, a phenanthrene group, a triphenylene group (benzo(9,10)phenanthrene group), a pyrene group, etc. Groups, cyclopentadienyl groups, 1,2,3,4-tetrahydronaphthalene groups, thiophene groups, furan groups, indole groups, benzoborane heterocyclopentadienyl groups, benzophosphane heterocyclopentadienyl groups, indene groups, benzothiophene groups, benzogermanium heterocyclopentadienyl groups, benzothiophene groups, benzoselenene groups, benzofuran groups, carbazole groups, dibenzoborane heterocyclopentadienyl groups, dibenzophosphane heterocyclopentadienyl groups, fluorene groups, dibenzothiophene groups, dibenzogermanium heterocyclopentadienyl groups, dibenzothiophene groups, dibenzoselenene groups, dibenzofuran groups, dibenzothiophene 5-oxide groups, 9H-fluorene-9-one groups, dibenzothiophene 5,5-dioxide groups, azidoindole groups, azidobenzoborane heterocyclopentadienyl groups, azidobenzophosphane heterocyclopentadienyl groups, azidoindene groups, azidoindene groups, azidoindole groups Benzothiophene group, azabenzogermanium heterocyclopentadiene group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, azadibenzoboron heterocyclopentadiene group, azadibenzophosphaceropentadiene group, azafluorene group, azadibenzothiophene group, azadibenzogermanium heterocyclopentadiene group, azadibenzothiophene group, azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluorene-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthrene-rhein group, pyrrole group, pyrazole group, imidazole group, triazole group azole group, iso- azole group, thiazole group, isothiazole group, Diazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzo[] azole group, benzothiazole group, benzo[] Diazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroquinoline group, adamantyl group, norbornene group or norbornene group.
[0080] In one or more embodiments,
[0081] In Formula 1, the ring CY1 can be a group represented by one of Formulas CY1-1 to CY1-26, and / or
[0082] In Formula 1, the ring CY2 can be a group represented by one of Formulas CY2-1 to CY2-19, and / or
[0083] In Formula 1, the ring CY3 can be a group represented by one of Formulas CY3-1 to CY3-18, and / or
[0084] In Formula 1, the ring CY4 can be a group represented by one of Formulas CY4-1 to CY4-26:
[0085]
[0086]
[0087]
[0088]
[0089] In equations CY1-1 to CY1-26, X 19 It can be O, S, C(R) 17 (R) 18 ), Si(R) 17 (R) 18 ) or N-[(L 19 ) b19 -(R 19 ) c19 ], R 17 To R 19 Each can be the same as defined with respect to R1, L 19 b19 and c19 can be the same as those defined for L1, b1 and c1, respectively. * indicates the binding site with M or Y1 in Formula 1, and *' indicates the binding site with T1 or ring CY2 in Formula 1.
[0090] In equations CY2-1 to CY2-19, X 29 It can be O, S, C(R) 27 (R) 28 ), Si(R) 27 (R) 28 ) or N-[(L 29 ) b29 -(R 29 ) c29 ], R 27 To R 29 Each can be the same as defined with respect to R2, L 29 b29 and c29 can be the same as those defined for L2, b2 and c2, respectively. * indicates the binding site with M or Y2 in Formula 1, *' indicates the binding site with T1 or CY1 in Formula 1, and *" indicates the binding site with T2 or CY3 in Formula 1.
[0091] In equations CY3-1 to CY3-18, X 39 It can be O, S, C(R) 37 (R) 38 ), Si(R) 37 (R) 38 ) or N-[(L 39 ) b39 -(R 39) c39 ], R 37 To R 39 Each can be the same as defined with respect to R3, L 39 b39 and c39 can be the same as those defined for L3, b3 and c3, respectively. * indicates the binding site with M or Y3 in Formula 1, *" indicates the binding site with T2 or CY2 in Formula 1, and *' indicates the binding site with T3 or CY4 in Formula 1.
[0092] In equations CY4-1 to CY4-26, X 49 It can be O, S, C(R) 47 (R) 48 ), Si(R) 47 (R) 48 ) or N-[(L 49 ) b49 -(R 49 ) c49 ], R 47 To R 49 Each can be the same as defined with respect to R4, L 49 b49 and c 49 These can be the same as those defined for L4, b4, and c4, respectively. * indicates the binding site with M or Y4 in Formula 1, and *' indicates the binding site with T3 or CY3 in Formula 1.
[0093] In Equation 1, T1 can be a single bond, a double bond, or *-N(R) 51 )-*'、*-B(R 51 )-*'、*-P(R 51 )-*'、*-C(R 51 (R) 52 )-*'、*-Si(R 51 (R) 52 )-*'、*-Ge(R 51 (R) 52 )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R 51 )=*'、*=C(R 51 )-*'、*-C(R 51 )=C(R 52 )-*', *-C(=S)-*', or *-C≡C-*', T2 can be a single bond, a double bond, or *-N(R 53 )-*'、*-B(R 53 )-*'、*-P(R 53 )-*'、*-C(R 53 (R)54 )-*'、*-Si(R 53 (R) 54 )-*'、*-Ge(R 53 (R) 54 )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R 53 )=*'、*=C(R 53 )-*'、*-C(R 53 )=C(R 54 )-*', *-C(=S)-*', or *-C≡C-*', and T3 can be a single bond, a double bond, or *-N(R 55 )-*'、*-B(R 55 )-*'、*-P(R 55 )-*'、*-C(R 55 (R) 56 )-*'、*-Si(R 55 (R) 56 )-*'、*-Ge(R 55 (R) 56 )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R 55 )=*'、*=C(R 55 )-*'、*-C(R 55 )=C(R 56 )-*', *-C(=S)-*', or *-C≡C-*'.
[0094] For example, in Formula 1, the cyclic CY2 can be benzo[a] The azole group, benzothiazole group, or benzimidazole group, and T1 to T3 can each be a single bond.
[0095] In one or more embodiments, in Formula 1, the ring CY2 may be a pyridine group, pyrimidine group, pyridazine group, pyrazine group, triazine group, quinoline group, isoquinoline group, azirfluorene group, azircarbazole group, azirdibenzofuran group or azirdibenzothiophene group, and at least one of T1 to T3 may not be a single bond.
[0096] In Equation 2, Het1 can be a nitrogen-containing C1-C lacking π electrons. 30 Cyclic groups.
[0097] In Equation 3-1, the ring CY 71 and CY 72 Each can independently be a π-electron-rich C3-C30 Cyclic groups, and cyclic CY 71 and CY 72 Optionally via unsubstituted or by at least one R 10a Replacement of π-electron-rich C3-C 30 Cyclic groups are linked together.
[0098] In this specification, the term "π-electron-deficient nitrogen-containing cyclic group" refers to a heterocyclic group comprising *=N-*' as a cyclic moiety, and may be, for example, i) a third ring, ii) a fused ring in which two or more third rings are fused together, or iii) a fused ring in which one or more third rings are fused with one or more fourth rings. In this specification, the term "π-electron-deficient nitrogen-containing C1-C" is used to refer to a heterocyclic group. 30 "Cyclic groups" refer to nitrogen-containing cyclic groups that lack π electrons and have 1 to 30 carbon atoms.
[0099] In this specification, the term "π-electron-rich cyclic group" refers to a carbocyclic or heterocyclic group that does not include *=N-*' as the cyclic moiety, and may be, for example, i) a fourth ring or ii) a fused ring in which two or more fourth rings are fused together. In this specification, the term "π-electron-rich C1-C..." 30 "Cyclic groups" refer to cyclic groups rich in π electrons that have 3 to 30 carbon atoms.
[0100] In this specification, "third ring" may be an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, or a [missing information - likely a specific group or designation]. azole group, iso- azole group, azathiophene group, triazole group, tetraazole group, Diazole group, thiadiazole group, pyridine group, pyrazine group, pyridazine group, pyrimidine group, or triazine group.
[0101] In this specification, "fourth ring" may be a phenyl group, a cyclopentadienyl group, a pyrrole group, a furan group, a thiophene group, or a thiorrole group.
[0102] "A nitrogen-containing cyclic group lacking π electrons" can be, for example, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, etc. azole group, iso- Azolium group, pyridine group, pyrazine group, pyridazine group, pyrimidine group, indazole group, purine group, quinoline group, isoquinoline group, benzo[a]quinoline group, benzo[a]isoquinoline group, phthalazine group, naphthidine group, quinoxaline group, benzo[a]quinoxaline group, quinazolinine group, phenanthridine group, acridine group, phenanthrene-rhein group, phenazine group, benzimidazole group, isobenzothiazole group, benzo[a] azole group, isobenzo azole group, triazole group, tetraazole group The groups used in this disclosure include diazole groups, triazine groups, thiadiazole groups, imidazopyridine groups, imidazopyrimidine groups, azacarbazole groups, azadibenzofuranyl groups, azadibenzothiophene groups, azadibenzothiophene groups, pyridopyrazine groups, pyrrolophene groups, furanophene groups, or thiophene groups, but the embodiments thereof are not limited thereto.
[0103] "π-electron-rich cyclic groups" can be, for example, phenyl groups, heptadene groups, indene groups, naphthyl groups, etc. Group, indole group, acenaphthene group, fluorene group, spirodifluorene group, benzo[a]fluorene group, dibenzo[a]fluorene group, phenanthracene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, Group, tetraphenyl group, Groups, perylene groups, pentaphenyl groups, hexaphenyl groups, pentanfen groups, rutin groups, halophenyl groups, ovoid phenyl groups, pyrrole groups, furan groups, thiophene groups, isoindole groups, indole groups, benzofuran groups, benzothiophene groups, benzothiophene groups, naphthopyrrole groups, naphthofuran groups, naphthothiophene groups, naphthothiophene groups, benzocarbazole groups, dibenzocarbazole groups, dibenzofuran groups, dibenzothiophene groups, dibenzocarbazole groups, dibenzofuran groups, dibenzothiophene groups, dibenzocarbazole groups, dibenzocarbazole groups, dibenzofuran groups, dibenzothiophene groups, dibenzocarbazole groups, dibenzocarbazole groups, dibenzocarbazole groups, dibenzofuran groups, dibenzocarbazole ... The groups include thiophene sulfone group, carbazole group, dibenzothiophene group, indole-carbazole group, indolo-carbazole group, benzofuran-carbazole group, benzothiophene-carbazole group, benzothiophene-carbazole group, triindolophenyl group, acridine group, dihydroacridine group, benzonaphthuran group, benzonaphthiophene group, (indolo)phenanthrene group, (benzofuran-)phenanthrene group, or (benzothiophene-)phenanthrene group, but the embodiments of this disclosure are not limited thereto.
[0104] In one or more embodiments, Het1 in Formula 2 may be a group represented by one of Formulas 2-1 to 2-42:
[0105]
[0106] In one or more embodiments, the term in Equation 3-1 is used... The group represented may be any group represented by one of formulas 3(1) to 3(96):
[0107]
[0108]
[0109]
[0110]
[0111]
[0112] In equations 3(1) to 3(96),
[0113] X 71 It may be the same as the following description,
[0114] X 72 For O, S, N(R) 78a ), C(R 78a (R) 78b ), or Si(R) 78a (R) 78b ),
[0115] X 73 For O, S, N(R) 79a ), C(R 79a (R) 79b ), or Si(R) 79a (R) 79b ),and
[0116] R 78a R 78b R 79a and R 79b Each can be related to R. 71 The definitions are the same.
[0117] In equation 3-1, X 71 It can be O, S, N-(L) 75 ) b75 -(R 75 ) a75 C(R) 75 (R) 76 ), or Si(R) 75 (R) 76 ).
[0118] In equation 3-1, L 79 It can be a single bond, unsubstituted, or bonded by at least one R. 10a Replacement of π-electron-rich C3-C 30 Cyclic groups; or they may not exist.
[0119] In Equation 2, n can be an integer from 1 to 10. When n is 2 or greater, two or more are represented by *-(L 61 ) b61 -(R 61 ) a61 The groups represented may be the same or different from each other. For example, n in Formula 3 may be 1, 2 or 3, but the embodiments of this disclosure are not limited thereto.
[0120] In Equation 3-1, m can be 1, 2, or 3. When m is 1, L 79It may not exist. For example, m in formula 3-1 can be 1 or 2.
[0121] In equations 1, 2, and 3-1 to 3-4, L1 to L4, L 61 L 75 and L 81 To L 87 Each can be independently a single bond, unsubstituted, or bonded by at least one R. 10a Replacement C5-C 30 Carbocyclic group, or unsubstituted or with at least one R 10a Replacement C1-C 30 Heterocyclic groups.
[0122] For example, in equations 1, 2, and 3-1 to 3-4, L1 to L4, L 61 L 75 and L 81 To L 87 Each can independently be a phenyl group, a heptadene group, an indene group, or a naphthyl group. Group, indole group, acenaphthene group, fluorene group, spirodifluorene group, benzo[a]fluorene group, dibenzo[a]fluorene group, phenanthracene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, alkyl, tetraphenyl group, Groups, perylene group, pentanylphenyl group, hexaphenyl group, pentaphenyl group, rutin group, halophenyl group, ovoid phenyl group, pyrrole group, furan group, thiophene group, isoindole group, indole group, benzofuran group, benzothiophene group, benzothiophene group, naphthopyrrole group, naphthofuran group, naphthothiophene group, naphthothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzofuran group, dibenzothiophene group, dibenzothiophene sulfone group, carbazole group, dibenzothiophene group, indolecarbazole group, indolecarbazole group, benzofuran-carbazole group, benzothiophene-carbazole group, benzothiophene-carbazole group, triindole-phenyl group, acridine group, dihydroacridine group, imidazole group, pyrazole group, thiazole group, isothiazole group, azole group, iso- Azolium group, pyridine group, pyrazine group, pyridazine group, pyrimidine group, indazole group, purine group, quinoline group, isoquinoline group, benzo[a]quinoline group, benzo[a]isoquinoline group, phthalazine group, naphthidine group, quinoxaline group, benzo[a]quinoxaline group, quinazolinine group, phenanthridine group, phenanthroxaline group, phenazine group, benzimidazole group, isobenzothiazole group, benzo[a] azole group, isobenzo azole group, triazole group, tetraazole group The following groups are included: diazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group, azacarbazole group, azabenzofuran group, azadibenzothiophene group, azadibenzothiophene group, benzonaphthofuran group, benzonaphthothiophene group, (indolo)phenanthrene group, (benzofurano)phenanthrene group, or (benzothiophene)phenanthrene group, each of which is unsubstituted or substituted by at least one R group. 10a replace.
[0123] In one or more embodiments, L in formulas 3-1 to 3-4 75 and L 81 To L 87 Each can be independently unsubstituted or by at least one R 10a Replacement of π-electron-rich C3-C 30 Cyclic groups.
[0124] In one or more embodiments, L in formulas 3-1 to 3-4 75 and L 81 To L 87 Each can be independently unsubstituted or by at least one R 10a Substituted phenyl groups, or unsubstituted or substituted with at least one R 10a The substitute group is represented by one of formulas 3(1) to 3(96), but the embodiments of this disclosure are not limited thereto.
[0125] In equations 1, 2, and 3-1 to 3-4, b1 to b4, b61, b75, and b81 to b87 respectively represent L1 to L4, L... 61 L 75 and L 81 To L 87 The number of, and each can be an integer from 1 to 10 (e.g., 1, 2 or 3).
[0126] In equations 1, 2, and 3-1 to 3-4, R a R b R1 to R4, R 51 To R 56 R 61 R 62 R 71 R 72 R 75 R 76 and R 81 To R 86 Each of these groups can independently be hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl group, cyano group, nitro group, amidine group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C 60Alkyl groups, substituted or unsubstituted C2-C 60 alkenyl groups, substituted or unsubstituted C2-C 60 alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C2-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C2-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thioyl groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -B(Q6)(Q7), or -P(=O)(Q8)(Q9). Q1 to Q9 may be the same as those described below.
[0127] In one or more embodiments, R in formulas 1, 2, and 3-1 to 3-4 a R b R1 to R4, R 51 To R 56 R 61 R 62 R 71 R 72 R 75 R 76 and R 81 To R 86 Each can be independently:
[0128] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidine group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, -SF5, C1-C 20 alkyl groups or C1-C 20 Alkoxy group;
[0129] Each of the following C1-C is replaced: 20 alkyl groups or C1-C 20Alkoxy groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl groups, cyano groups, nitro groups, amino groups, amidine groups, hydrazine groups, hydrazone groups, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C1-C 10 Alkyl groups, cyclopentyl groups, cyclohexyl groups, cycloheptyl groups, cyclooctyl groups, adamantyl groups, norbornenyl groups, cyclopentenyl groups, cyclohexenyl groups, cycloheptenyl groups, bicyclic [1.1.1]pentyl groups, bicyclic [2.1.1]hexyl groups, bicyclic [2.2.1]heptyl groups, bicyclic [2.2.2]octyl groups, phenyl groups, (C1-C 20 Alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, pyridyl group, pyrimidinyl group or any combination thereof;
[0130] Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.1]heptyl group, bicyclo[2.2.2]octyl group, phenyl group, (C1-C 20 Alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthrene group, anthracene group, fluoranthracene group, triphenylene group, pyrene group, alkyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazole group, pyrazolyl group, thiazolyl group, isothiazolyl group, azole group, iso Azolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazole group, purine group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cyclophosphinyl group, carbazole group, phenanthroline group, benzimidazole group, benzofuranyl group, benzothiophene group, isobenzothiazolyl group, benzo[] azole group, isobenzo azole group, triazole group, tetraazole group The diazolyl group, triazine group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazole group, dibenzocarbazole group, imidazopyridyl group, imidazopyrimidinyl group, azacarbazole group, azadibenzofuranyl group, or azadibenzothiophenyl group, each unsubstituted or substituted with the following: deuterium, F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidoyl group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.1]heptyl group, bicyclo[2.2.2]octyl group, phenyl group, (C1-C 20 Alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthryl group, anthracene group, fluoranthracene group, terphenyl group, pyrene group, alkyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazole group, pyrazolyl group, thiazolyl group, isothiazolyl group, azole group, iso Azolyl group, pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazole group, purine group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cyclophosphinyl group, carbazole group, phenanthroline group, benzimidazole group, benzofuranyl group, benzothiophene group, isobenzothiazolyl group, benzo[] azole group, isobenzo azole group, triazole group, tetraazole group Diazolyl group, triazine group, dibenzofuranyl group, dibenzothiophene group, benzocarbazole group, dibenzocarbazole group, imidazopyridyl group, imidazopyrimidine group, azacarbazole group, azadibenzofuranyl group, azadibenzothiophene group, -Si(Q) 33 (Q) 34 (Q) 35 ), or any combination thereof; or
[0131] -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9), and
[0132] Q1 to Q9 and Q 33 To Q 35 Each can be independently:
[0133] -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; or
[0134] n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neopentyl group, isopentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, phenyl group, biphenyl group or naphthyl group, each unsubstituted or deuterated, C1-C 10 Alkyl groups, phenyl groups, or any combination thereof are substituted.
[0135] In one or more embodiments, R in formulas 1, 2, and 3-1 to 3-4 a R b R1 to R4, R 51 To R 56 R 61 R 62 R 71 R 72 R 75 R 76 and R 81 To R 86 Each of these can be independently hydrogen, deuterium, -F, cyano group, nitro group, -SF5, -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a group represented by any one of formulas 9-1 to 9-66, a group represented by any one of formulas 9-1 to 9-66 wherein at least one hydrogen is replaced by deuterium, a group represented by any one of formulas 10-1 to 10-249 wherein at least one hydrogen is replaced by deuterium, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5) or -B(Q6)(Q7) (where Q1 to Q7 can be the same as described above):
[0136]
[0137]
[0138]
[0139]
[0140]
[0141]
[0142] In formulas 9-1 to 9-66 and 10-1 to 10-249, * indicates a binding site with an adjacent atom, Ph indicates a phenyl group, and TMS indicates a trimethylsilyl group.
[0143] "A group represented by one of formulas 9-1 to 9-66 in which at least one hydrogen atom is replaced by deuterium" can be, for example, a group represented by one of formulas 9-501 to 9-552:
[0144]
[0145]
[0146] "A group in which at least one hydrogen atom is replaced by deuterium, represented by one of formulas 10-1 to 10-249" can be, for example, a group represented by one of formulas 10-501 to 10-510:
[0147]
[0148] In Equation 1, c1 to c4 each represent the number of groups R1 to R4, and each can be an integer from 0 to 10 independently.
[0149] In equations 1, 2, and 3-1 to 3-4, a1 to a4, a61, a62, a71, a72, a75, and a81 to a86 can each be an integer from 0 to 20 independently.
[0150] In one or more embodiments, R in formulas 3-1 to 3-4 71 R 72 R 75 R 76 and R 81 To R 86 Each can be independently hydrogen, deuterium, or C1-C 20 alkyl groups, unsubstituted or with at least one R 10a Replacement of π-electron-rich C3-C 30 Cyclic groups, -N(Q1)(Q2) or -Si(Q3)(Q4)(Q5), but the embodiments of this disclosure are not limited thereto.
[0151] In Equation 1, R a R b R1 to R4 and R 51 To R 56 Two or more may optionally be connected to each other to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 30 Heterocyclic groups.
[0152] In this specification, R 10a It can be the same as that defined for R1.
[0153] In this specification, unless otherwise described, *, *' and *" each represent a binding site with an adjacent atom.
[0154] In one or more embodiments, in Formula 1,
[0155] a1 to a4 can each be an independent integer from 1 to 20, and
[0156] At least one of R1 to R4 can be independently either substituted or unsubstituted C1-C. 60 alkoxy group, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C2-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C2-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C6-C 60 aryloxy group, substituted or unsubstituted C6-C 60 aryl thioyl groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic fused polycyclic groups, substituted or unsubstituted monovalent non-aromatic fused heterocyclic groups, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5) or -B(Q6)(Q7).
[0157] In one or more embodiments, in Formula 1,
[0158] 1) Cyclic CY2 can be benzo[a] The azole group, benzothiazole group, benzimidazole group, benzozathiol group, or benzopyrrole group, a1 to a4 may each be an integer from 1 to 20 independently, and at least one of R1 to R4 may each be a substituted or unsubstituted C3-C group. 10Cycloalkyl groups, substituted or unsubstituted C2-C 10 Heterocyclic alkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C2-C 10 Heterocyclic alkenyl groups, substituted or unsubstituted C6-C 60 aryl group, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted monovalent nonaromatic fused polycyclic groups, or substituted or unsubstituted monovalent nonaromatic fused heterocyclic groups, or
[0159] 2) Cyclic CY2 may be a pyridine group, a1 to a4 may each be an integer from 1 to 20, and at least one of R1 to R4 may each be a substituted or unsubstituted C1-C group. 60 alkoxy group, substituted or unsubstituted C6-C 60 Aryloxy groups, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5) or -B(Q6)(Q7).
[0160] In one or more embodiments,
[0161] L in equations 3-1 to 3-4 75 L 79 and L 81 To L 87 Each can be an unsubstituted or π-electron-rich C3-C, either individually or substituted with the following: 30 Cyclic groups: deuterium, C1-C 20 Alkyl groups, C1-C 20 Alkoxy groups, phenyl groups, naphthyl groups, anthracene groups, phenanthrene groups, triphenylene groups, fluorene groups, di(C1-C) 10 alkyl)fluorenyl group, di(C6-C) 60 aryl)fluorenyl group, dibenzothiol group, di(C1-C 10 alkyl)dibenzothiol group, di(C6-C 60 Aryl) dibenzothioyl group, carbazole group, (C1-C 10 alkyl)carbazole group, (C6-C 60 Aryl)carbazolyl group, dibenzofuranyl group, dibenzothiophene group, biphenyl group, triphenyl group, tetraphenyl group, -N(Q) 31 (Q) 32 ), or any combination thereof; or L in Equation 3-1 79 It can be a single bond, and / or
[0162] R in equations 3-1 to 3-4 71 R 72 R75 R 76 and R 81 To R 86 Each can be independently:
[0163] Hydrogen or deuterium;
[0164] Unsubstituted or substituted C1-C 20 Alkyl groups: deuterium, phenyl, naphthyl, anthracene, phenanthrene, triphenylene, fluorene, di(C1-C2) 10 alkyl)fluorenyl group, di(C6-C) 60 aryl)fluorenyl group, dibenzothiol group, di(C1-C 10 alkyl)dibenzothiol group, di(C6-C 60 Aryl) dibenzothioyl group, carbazole group, (C1-C 10 alkyl)carbazole group, (C6-C 60 Aryl)carbazole group, dibenzofuranyl group, dibenzothiophene group, biphenyl group, triphenyl group, tetraphenyl group, -N(Q) 31 (Q) 32 ), or any combination thereof;
[0165] Unsubstituted or π-electron-rich C3-C 30 Cyclic groups: deuterium, C1-C 20 Alkyl groups, C1-C 20 Alkoxy groups, phenyl groups, naphthyl groups, anthracene groups, phenanthrene groups, triphenylene groups, fluorene groups, di(C1-C) 10 alkyl)fluorenyl group, di(C6-C) 60 aryl)fluorenyl group, dibenzothiol group, di(C1-C 10 alkyl)dibenzothiol group, di(C6-C 60 Aryl) dibenzothioyl group, carbazole group, (C1-C 10 alkyl)carbazole group, (C6-C 60 Aryl)carbazolyl group, dibenzofuranyl group, dibenzothiophene group, biphenyl group, triphenyl group, tetraphenyl group, -N(Q) 31 (Q) 32 ), or any combination thereof; or
[0166] -N(Q1)(Q2),
[0167] However, the implementation of this disclosure is not limited thereto.
[0168] In one or more embodiments, at least one of the second and third compounds (e.g., all of the second and third compounds) may include a carbazole group.
[0169] In one or more embodiments, at least one of the second and third compounds may each be independently a compound represented by formula 3-1, wherein X in formula 3-1 71 It can be N-(L) 75 ) b75 -(R 75 ) a75 .
[0170] In one or more embodiments, at least one of the second and third compounds may not include a carbazole group.
[0171] In one or more embodiments, at least one of the second and third compounds may each be a compound represented by one of formulas 3-2 to 3-4.
[0172] In one or more embodiments, at least one of the second and third compounds may each be a compound represented by one of formulas 3-2 to 3-4, wherein the compound represented by formulas 3-2 to 3-4 may include a carbazole group.
[0173] In one or more embodiments, at least one of the second and third compounds may each be independently a compound represented by one of formulas 3-2 to 3-4, and the compound represented by formulas 3-2 to 3-4 may not include a carbazole group.
[0174] In one or more embodiments, in formula 3-3, R 81 and R 82 They can be linked to each other via single bonds or (dimethyl)methylene groups, and / or R 83 and R 84 They can be linked to each other via single bonds or (dimethyl)methylene groups (e.g., see compound H2-27 below).
[0175] In one or more embodiments, in formulas 3-4, R 81 and R 82 They can be linked to each other via single bonds or (dimethyl)methylene groups, and / or R 83 and R 84 They can be linked to each other via single bonds or (dimethyl)methylene groups, and / or R 85 and R 86 They can be linked to each other via single bonds or (dimethyl)methylene groups.
[0176] In one or more embodiments, the Pt-containing organometallic compound may be a compound represented by formula 1-1 or 1-2:
[0177]
[0178] In equations 1-1 and 1-2,
[0179] M, Y1 to Y4, X1 to X4, and T1 to T3 can each be the same as described above.
[0180] X 11 It can be N or C-[(L 11 ) b11 -(R 11 ) c11 ], X 12 It can be N or C-[(L 12 ) b12 -(R 12 ) c12 ], X 13 It can be N or C-[(L 13 ) b13 -(R 13 ) c13 ], and X 14 It can be N or C-[(L 14 ) b14 -(R 14 ) c14 ],
[0181] L 11 To L 14 b11 to b14, R 11 To R 14 And c11 to c14 can each be the same as those defined with respect to L1, b1, R1 and c1 respectively.
[0182] X 21 It can be N or C-[(L 21 ) b21 -(R 21 ) c21 ], X 22 It can be N or C-[(L 22 ) b22 -(R 22 ) c22 ], and X 23 It can be N or C-[(L 23 ) b23 -(R 23 ) c23 ],
[0183] L 21 To L 23 b21 to b23, R 21 To R 23And c21 to c23 can each be the same as those defined with respect to L2, b2, R2 and c2 respectively.
[0184] X 29 It can be O, S, C(R) 27 (R) 28 ), Si(R) 27 (R) 28 ), or N-[(L 29 ) b29 -(R 29 ) c29 ],
[0185] R 27 To R 29 Each can be the same as defined with respect to R2, and L 29 b29 and c29 can each be the same as those defined with respect to L2, b2 and c2, respectively.
[0186] X 31 It can be N or C-[(L 31 ) b31 -(R 31 ) c31 ], X 32 It can be N or C-[(L 32 ) b32 -(R 32 ) c32 ], and X 33 It can be N or C-[(L 33 ) b33 -(R 33 ) c33 ],
[0187] L 31 To L 33 b31 to b33, R 31 To R 33 And c31 to c33 can each be the same as those defined with respect to L3, b3, R3 and c3 respectively.
[0188] X 41 It can be N or C-[(L 41 ) b41 -(R 41 ) c41 X 42 It can be N or C-[(L 42 ) b42 -(R 42 ) c42 ], X 43 It can be N or C-[(L 43 ) b43 -(R 43 ) c43], and X 44 It can be N or C-[(L 44 ) b44 -(R 44 ) c44 ],
[0189] L 41 To L 44 b41 to b44, R 41 To R 44 And c41 to c44 can each be the same as those defined with respect to L4, b4, R4 and c4 respectively.
[0190] R 11 To R 14 The two can optionally be connected to each other to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 30 Heterocyclic groups,
[0191] R 21 To R 23 The two can optionally be connected to each other to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 30 Heterocyclic groups,
[0192] R 31 To R 33 The two can optionally be connected to each other to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 30 Heterocyclic groups, and
[0193] R 41 To R 44 The two can optionally be connected to each other to form an unsubstituted or R-shaped structure. 10a Replacement C5-C 30 The carbocyclic group is either unsubstituted or has at least one R group. 10a Replacement C1-C 30 Heterocyclic groups.
[0194] In this specification, "unsubstituted or by at least one R" 10a Replacement C5-C 30 "Carbocyclic group" and "unsubstituted or with at least one R" 10aReplacement C1-C 30 Heterocyclic groups include cyclopentyl groups, cyclohexyl groups, cycloheptyl groups, cyclooctyl groups, adamantyl groups, norbornene groups, cyclopentenyl groups, cyclohexenyl groups, cycloheptenyl groups, cyclooctenyl groups, bicyclic [1.1.1]pentyl groups, bicyclic [2.1.1]hexyl groups, bicyclic [2.2.1]heptyl groups, bicyclic [2.2.2]octyl groups, phenyl groups, heptalene groups, indene groups, naphthyl groups, Group, indole group, acenaphthene group, fluorene group, spirodifluorene group, benzo[a]fluorene group, dibenzo[a]fluorene group, phenanthracene group, anthracene group, fluoranthene group, triphenylene group, pyrene group, Group, tetraphenyl group, Groups, perylene group, pentanylphenyl group, hexaphenyl group, pentaphenyl group, rutin group, halophenyl group, ovoid phenyl group, pyrrole group, furan group, thiophene group, isoindole group, indole group, benzofuran group, benzothiophene group, benzothiophene group, naphthopyrrole group, naphthofuran group, naphthothiophene group, naphthothiophene group, benzocarbazole group, dibenzocarbazole group, dibenzofuran group, dibenzothiophene group, dibenzothiophene sulfone group, carbazole group, dibenzothiophene group, indolecarbazole group, indolecarbazole group, benzofuran-carbazole group, benzothiophene-carbazole group, benzothiophene-carbazole group, triindole-phenyl group, acridine group, dihydroacridine group, imidazole group, pyrazole group, thiazole group, isothiazole group, azole group, iso- Azolium group, pyridine group, pyrazine group, pyridazine group, pyrimidine group, indazole group, purine group, quinoline group, isoquinoline group, benzo[a]quinoline group, benzo[a]isoquinoline group, phthalazine group, naphthidine group, quinoxaline group, benzo[a]quinoxaline group, quinazolinine group, phenanthridine group, phenanthroxaline group, phenazine group, benzimidazole group, isobenzothiazole group, benzo[a] azole group, isobenzo azole group, triazole group, tetraazole group The following groups are included: diazole group, triazine group, thiadiazole group, imidazopyridine group, imidazopyrimidine group, azacarbazole group, azadibenzofuranyl group, azadibenzothiophene group, azadibenzothiophene group, pyrrolophenanthrene group, furanolphenanthrene group, thiophene group, benzonaphthuranyl group, benzonaphthiophene group, (indophenanthrene)phenanthrene group, (benzofuranol)phenanthrene group, and (benzothiophene)phenanthrene group, each unsubstituted or substituted with at least one R 10a The implementation of this disclosure may be alternative, but is not limited thereto.
[0195] In this specification, "C1-C" 60Examples of "alkyl groups" include methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, sec-butyl groups, isobutyl groups, tert-butyl groups, n-pentyl groups, tert-pentyl groups, neopentyl groups, isopentyl groups, sec-pentyl groups, 3-pentyl groups, sec-isopentyl groups, n-hexyl groups, isohexyl groups, sec-hexyl groups, tert-hexyl groups, n-heptyl groups, isoheptyl groups, sec-heptyl groups, tert-heptyl groups, n-octyl groups, isooctyl groups, sec-octyl groups, tert-octyl groups, n-nonyl groups, isononyl groups, sec-nonyl groups, tert-nonyl groups, n-decyl groups, isodecyl groups, sec-decyl groups, and tert-decyl groups, but the embodiments of this disclosure are not limited thereto.
[0196] In this specification, "C3-C" 10 Examples of "cycloalkyl groups" include cyclopentyl groups, cyclohexyl groups, cycloheptyl groups, cyclooctyl groups, adamantyl groups, bicyclo[1.1.1]pentyl groups, bicyclo[2.1.1]hexyl groups, bicyclo[2.2.1]heptyl groups, and bicyclo[2.2.2]octyl groups, but the embodiments of this disclosure are not limited thereto.
[0197] The Pt-containing organometallic compounds may be one of compounds 1-1 to 1-88, 2-1 to 2-47, 3-1 to 3-591, and D1 to D24, but the embodiments of this disclosure are not limited thereto:
[0198]
[0199]
[0200]
[0201]
[0202]
[0203]
[0204]
[0205]
[0206]
[0207]
[0208]
[0209]
[0210]
[0211]
[0212]
[0213]
[0214]
[0215]
[0216]
[0217]
[0218]
[0219]
[0220]
[0221]
[0222]
[0223]
[0224]
[0225]
[0226]
[0227]
[0228]
[0229]
[0230]
[0231]
[0232] The first compound may be one of compounds H1-1 to H1-75, but the embodiments of this disclosure are not limited thereto:
[0233]
[0234]
[0235]
[0236]
[0237]
[0238] The second and third compounds may each be independently one of compounds H2-1 to H2-73, but the embodiments of this disclosure are not limited thereto:
[0239]
[0240]
[0241]
[0242]
[0243] In one or more embodiments, the composition may satisfy Equation 1 and Equation 2:
[0244] Equation 1
[0245] HOMO(H2)>HOMO(D)
[0246] Equation 2
[0247] HOMO(H3)>HOMO(D).
[0248] In equations 1 and 2,
[0249] HOMO(H2) is the absolute value of the HOMO energy level of the second compound.
[0250] HOMO(H3) is the absolute value of the HOMO energy level of the third compound, and
[0251] HOMO(D) is the absolute value of the HOMO energy level of a Pt-containing organometallic compound.
[0252] In one or more embodiments, the absolute value of the HOMO energy level of the second compound and the absolute value of the HOMO energy level of the Pt-containing organometallic compound may be 0.05 eV to 0.6 eV, for example, 0.05 eV to 0.3 eV, and the absolute value of the HOMO energy level of the third compound and the absolute value of the HOMO energy level of the Pt-containing organometallic compound may be 0.05 eV to 0.6 eV, for example, 0.05 eV to 0.3 eV.
[0253] The weight ratio of the second compound to the third compound can be from 9:1 to 1:9, for example from 2:7 to 7:2, but the embodiments of the present disclosure are not limited thereto.
[0254] Compositions comprising Pt-containing organometallic compounds, a first compound, a second compound, and a third compound can be suitably used as organic layers, such as emitting layers, in organic light-emitting devices. Another aspect of this disclosure provides an organic light-emitting device comprising: a first electrode; a second electrode; and an organic layer disposed between the first and second electrodes and comprising an emitting layer, wherein the organic layer comprises the aforementioned composition.
[0255] Organic light-emitting devices include the composition comprising a Pt-containing organometallic compound, a first compound, a second compound, and a third compound, such that the organic light-emitting device can have improved external quantum luminescence efficiency, improved driving voltage, and improved lifetime characteristics.
[0256] This composition can be used between electrode pairs in an organic light-emitting device. For example, the emitting layer may include the composition. Here, a Pt-containing organometallic compound can be used as a dopant, and the first, second, and third compounds can each be used as the host.
[0257] Organic light-emitting devices comprising the composition may emit red, green, or blue light. For example, organic light-emitting devices comprising the composition may emit green light, but embodiments of this disclosure are not limited thereto.
[0258] The first electrode may be the anode serving as a hole injection electrode, and the second electrode may be the cathode serving as an electron injection electrode; or, the first electrode may be the cathode serving as an electron injection electrode, and the second electrode may be the anode serving as a hole injection electrode.
[0259] In one or more embodiments, in an organic light-emitting device, the first electrode may be an anode, the second electrode may be a cathode, and the organic layer may further include a hole transport region between the first electrode and the emitting layer and an electron transport region between the emitting layer and the second electrode, wherein the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer or any combination thereof, and the electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer or any combination thereof.
[0260] As used herein, the term "organic layer" refers to a single layer and / or multiple layers between the first and second electrodes of an organic light-emitting device. In addition to organic compounds, "organic layer" may include organometallic complexes containing metals.
[0261] Figure 1 This is a schematic cross-sectional view of the organic light-emitting device 10 according to an embodiment. In the following text, it will be referred to in conjunction with... Figure 1 The structure of an organic light-emitting device according to an embodiment and a method for manufacturing an organic light-emitting device according to an embodiment are described. The organic light-emitting device 10 includes a first electrode 11, an organic layer 15, and a second electrode 19 stacked sequentially.
[0262] A substrate may be additionally disposed below the first electrode 11 or above the second electrode 19. Any substrate used in conventional organic light-emitting devices may be used as the substrate, and the substrate may be a glass substrate or a transparent plastic substrate, each of which has excellent mechanical strength, thermal stability, transparency, surface smoothness, processability and water resistance.
[0263] The first electrode 11 can be formed, for example, by depositing or sputtering a material for forming the first electrode 11 onto a substrate. The first electrode 11 may be an anode. The material used to form the first electrode 11 may include a material having a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a semi-reflective electrode, or a transmissive electrode. The material used to form the first electrode 11 may be, for example, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO). In one or more embodiments, the material used to form the first electrode 11 may be a metal, such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag).
[0264] The first electrode 11 may have a single-layer structure or a multi-layer structure including two or more layers. For example, the first electrode 11 may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 11 is not limited to this.
[0265] The organic layer 15 is disposed on the first electrode 11.
[0266] The organic layer 15 may include a hole transport region, an emitter layer, and an electron transport region.
[0267] The hole transport region can be located between the first electrode 11 and the emitter layer.
[0268] The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof.
[0269] The hole transport region may comprise only a hole injection layer or only a hole transport layer. In one or more embodiments, the hole transport region may have a hole injection layer / hole transport layer structure or a hole injection layer / hole transport layer / electron blocking layer structure, which are stacked sequentially from the first electrode 11 in the order stated herein. For example, the hole transport layer comprises at least two layers.
[0270] When the hole transport region includes a hole injection layer, the hole injection layer can be formed on the first electrode 11 by using one or more suitable methods such as vacuum deposition, spin coating, tape casting and / or Langmuir-Blodgett (LB) deposition.
[0271] When a hole injection layer is formed by vacuum deposition, the deposition conditions can vary depending on the material used to form the hole injection layer and the structure and thermal properties of the hole injection layer. For example, deposition conditions may include a deposition temperature of about 100°C to about 500°C, and about 10 -8 To about 10 -3 The vacuum pressure of Tor and the treaty to approximately The deposition rate. However, deposition conditions are not limited to this.
[0272] When spin coating is used to form a hole injection layer, the coating conditions can vary depending on the material used to form the hole injection layer and the structure and thermal properties of the hole injection layer. For example, the coating speed can be from about 2,000 rpm to about 5,000 rpm, and the temperature at which heat treatment is performed after coating to remove the solvent can be from about 80°C to about 200°C. However, the coating conditions are not limited to these.
[0273] The conditions for the formation of hole transport layers and electron blocking layers can be understood by referring to the conditions for the formation of hole injection layers.
[0274] Hole transport regions may include m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, spiro-TPD, spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4',4"-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-sulfonated styrene) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-sulfonated styrene) (PANI / PSS), compounds represented by formula 201 below, and compounds represented by formula 202 below, or any combination thereof:
[0275]
[0276] Formula 201
[0277]
[0278] Formula 202
[0279]
[0280] In Equation 201, Ar 101 and Ar 102 Each can be independently phenylene, cyclopentadienylene, indenylene, naphthylene, or phenylene. Alkyl, heptylene, acenaphthene, fluorene, phenenenyl, anthracene, fluorene, phenylenetriene, pyrene, etc. alkyl, tetraphenyl, phenyl The group consisting of a hydroxyl group, a perylene group, or a pentanephenyl group, each unsubstituted or substituted with the following: deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidoyl group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl groups, C2-C 60 alkenyl groups, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 10 Cycloalkyl groups, C3-C 10 Cycloalkenyl groups, C2-C 10 Heterocyclic alkyl groups, C2-C 10 Heterocyclic alkenyl groups, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 aryl thiols, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, or any combination thereof.
[0281] In Equation 201, xa and xb can each be an integer from 0 to 5, or they can be 0, 1, or 2. For example, xa can be 1 and xb can be 0, but xa and xb are not limited to these values.
[0282] R in equations 201 and 202 101 To R 108 R 111 To R 119 and R 121 To R 124 Each can be independently:
[0283] Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidine group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl groups (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.) or C1-C 10 Alkoxy groups (e.g., methoxy groups, ethoxy groups, propoxy groups, butoxy groups, pentoxy groups, etc.);
[0284] Each of the following C1-C is replaced: 10 alkyl groups or C1-C 10Alkoxy groups: deuterium, -F, -Cl, -Br, -I, hydroxyl groups, cyano groups, nitro groups, amino groups, amido groups, hydrazine groups, hydrazone groups, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, or any combination thereof; or
[0285] The phenyl group, naphthyl group, anthracene group, fluorenyl group, or pyrene group are either unsubstituted or substituted with the following: deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amido group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl groups, C1-C 10 alkoxy groups, or any combination thereof,
[0286] However, the implementation of this disclosure is not limited thereto.
[0287] In Equation 201, R 109 It may be a phenyl group, naphthyl group, anthracene group, or pyridyl group, each unsubstituted or substituted with the following: deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidine group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, phenyl group, naphthyl group, anthracene group, pyridyl group, or any combination thereof.
[0288] In one or more embodiments, the compound represented by formula 201 may be represented by formula 201A, but the embodiments of this disclosure are not limited thereto:
[0289] Formula 201A
[0290]
[0291] In Equation 201A, R 101 R 111 R 112 and R 109 Each can be the same as described above.
[0292] For example, the compound represented by formula 201 and the compound represented by formula 202 may each be one of compounds HT1 to HT20 or any combination thereof, but the embodiments of this disclosure are not limited thereto:
[0293]
[0294]
[0295] The thickness of the hole transport region can be approximately to approximately For example, about to approximately When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer can be approximately [missing information]. to approximately For example, about to approximately Within a certain range, and the thickness of the hole transport layer can be approximately... to approximately For example, about to approximately Within these ranges, satisfactory hole transport characteristics can be obtained without a significant increase in driving voltage when the hole transport region, hole injection layer, and hole transport layer thickness are within these ranges.
[0296] In addition to these materials, the hole transport region may further include charge-generating materials to improve conductivity. The charge-generating materials may be uniformly or non-uniformly dispersed in the hole transport region.
[0297] The charge-generating material may be, for example, a p-doper. The p-doper may include quinone derivatives, metal oxides, compounds containing a cyano group, or any combination thereof, but embodiments of this disclosure are not limited thereto. Non-limiting examples of p-dopers include: quinone derivatives such as tetracyanoquinone dimethylane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethylane (F4-TCNQ) or F6-TCNNQ; metal oxides such as tungsten oxide or molybdenum oxide; and compounds containing a cyano group such as, but not limited to, the following compound HT-D1:
[0298]
[0299] The hole transport region may include a buffer layer.
[0300] Furthermore, the buffer layer can compensate for the optical resonance distance according to the wavelength of the light emitted from the emission layer, and thus the efficiency of the formed organic light-emitting device can be improved.
[0301] Furthermore, when the hole transport region includes an electron blocking layer, the material used for the electron blocking layer may include the materials described above for hole transport layers, the materials for the body (which will be explained later), or any combination thereof. However, the materials used for the electron blocking layer are not limited to these. For example, when the hole transport region includes an electron blocking layer, the material used for the electron blocking layer may be mCP, which will be explained later.
[0302] The emitter layer can then be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, etc. When the emitter layer is formed by vacuum deposition or spin coating, the deposition or coating conditions can be similar to those used when forming the hole injection layer, although the deposition or coating conditions can be varied depending on the compound used to form the emitter layer.
[0303] The emitter layer may include the composition comprising a Pt-containing organometallic compound, a first compound, a second compound, and a third compound.
[0304] For example, the emitter layer may include a dopant and a host, wherein the dopant includes a Pt-containing organometallic compound, and the host includes a first compound, a second compound, and a third compound.
[0305] In addition to the composition, the emitter layer may also include additional dopants and / or additional host.
[0306] When the organic light-emitting device is a full-color organic light-emitting device, the emitting layer can be patterned as a red emitting layer, a green emitting layer, and / or a blue emitting layer. In one or more embodiments, due to the stacked structure including red, green, and / or blue emitting layers, the emitting layer can emit white light.
[0307] When the emitter layer comprises a host and a dopant, the amount of the dopant may range from about 0.01 parts by weight to about 20 parts by weight based on 100 parts by weight of the host, but the embodiments of this disclosure are not limited thereto.
[0308] The thickness of the emission layer can be approximately to approximately For example, about to approximately Within this range, excellent light emission characteristics can be obtained without a significant increase in driving voltage when the thickness of the emitting layer is within this range.
[0309] The electronic transmission area can be located on the emission layer.
[0310] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.
[0311] For example, the electron transport region may have a hole blocking layer / electron transport layer / electron injection layer structure or an electron transport layer / electron injection layer structure, but the structure of the electron transport region is not limited to these. The electron transport layer may have a multilayer structure or a single-layer structure comprising two or more different materials.
[0312] The conditions for forming the hole blocking layer, electron transport layer, and electron injection layer that constitute the electron transport region can be understood by referring to the conditions for forming the hole injection layer.
[0313] When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, BCP, Bphen, BAlq, or any combination thereof, but the embodiments of this disclosure are not limited thereto:
[0314]
[0315] The thickness of the hole-blocking layer can be approximately to approximately For example, about to approximately When the thickness of the hole blocking layer is within these ranges, the hole blocking layer can have excellent hole blocking characteristics without a significant increase in driving voltage.
[0316] The electron transport layer may include BCP, Bphen, Alq3, BAlq, TAZ, NTAZ, or any combination thereof:
[0317]
[0318] In one or more embodiments, the electronic transport layer may include one of ET1 to ET25 or any combination thereof, but is not limited thereto:
[0319]
[0320]
[0321]
[0322] The thickness of the electron transport layer can be approximately to approximately For example, about to approximately When the thickness of the electron transport layer is within the range described above, the electron transport layer can have satisfactory electron transport characteristics without a significant increase in driving voltage.
[0323] In addition to the materials described above, the electron transport layer may further include a material comprising metal.
[0324] The metal-containing material may include Li complexes. For example, the Li complexes may include ET-D1(Liq), ET-D2, or any combination thereof:
[0325]
[0326] The electron transport region may include an electron injection layer that facilitates the inflow of electrons from the second electrode 19 therein.
[0327] The electron-injected layer may include LiF, NaCl, CsF, Li2O, BaO, or any combination thereof.
[0328] The thickness of the electron injection layer can be approximately to approximately For example, about to approximately When the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics can be obtained without a significant increase in driving voltage.
[0329] The second electrode 19 is disposed on the organic layer 15. The second electrode 19 may be a cathode. The material used to form the second electrode 19 may include metals, alloys, conductive compounds, or combinations thereof having a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag) may be used as materials for forming the second electrode 19. For the fabrication of a top-emitting light-emitting device, a transmission electrode formed using ITO or IZO may be used as the second electrode 19.
[0330] The above text has already discussed... Figure 1 An organic light-emitting device according to an embodiment is described.
[0331] As used in this article, the term "C1-C" 60 "alkyl group" refers to a straight-chain or branched monovalent group of a saturated aliphatic hydrocarbon having 1-60 carbon atoms, and examples include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, and hexyl groups. The term "C1-C" is used as in this document. 60 "alkylene group" refers to a group with a C1-C2 bond structure. 60 Divalent groups with the same structure as alkyl groups.
[0332] As used in this article, the term "C1-C" 60 "Alkoxy group" refers to the group consisting of -OA 101 The monovalent group represented (where A) 101 For C1-C 60 Alkyl groups), and examples of such groups include methoxy groups, ethoxy groups, and isopropoxy groups.
[0333] As used in this article, the term "C2-C" 60 "Alkenyl group" refers to the group located at C2-C. 60 A hydrocarbon group having at least one carbon-carbon double bond at the middle or end of an alkyl group, and examples include vinyl groups, propenyl groups, and butenyl groups. As used herein, the term "C2-C" is used... 60 "Ideinyl group" refers to a group with a C2-C...60 Divalent groups with the same structure as alkenyl groups.
[0334] As used in this article, the term "C2-C" 60 "Alkyne group" refers to the group located at C2-C. 60 An alkyl group having at least one carbon-carbon triple bond at its middle or end, and examples include ethynyl and propynyl groups. As used herein, the term "C2-C" is used... 60 "Imyynyl group" refers to a group with a C2-C... 60 A divalent group with the same structure as the alkynyl group.
[0335] As used in this article, the term "C3-C" 10 "Cycloalkyl group" refers to a monocyclic saturated hydrocarbon group having 3-10 carbon atoms, and non-limiting examples include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cycloheptyl groups. The term "C3-C" is used herein. 10 "Cycloalkylene group" refers to a group with a C3-C6 bond structure. 10 A divalent group with the same structure as a cycloalkyl group.
[0336] As used in this article, the term "C2-C" 10 "Heterocyclic alkyl group" refers to a monovalent saturated monocyclic group having at least one N, O, P, Si, Se, Ge, B, or S as a cyclic atom and 2-10 carbon atoms, and non-limiting examples include tetrahydrofuranyl and tetrahydrothiophenyl groups. The term "C2-C" is used as is herein. 10 "Heterocyclic alkyl groups" refers to groups with C2-C... 10 Divalent groups with the same structure as heterocyclic alkyl groups.
[0337] As used in this article, the term "C3-C" 10 "Cycloalkenyl group" refers to a monovalent monocyclic group having 3-10 carbon atoms and at least one carbon-carbon double bond in its ring and not being aromatic, and non-limiting examples include cyclopentenyl, cyclohexenyl, and cycloheptenyl groups. The term "C3-C" is used herein. 10 "Iridyl group" refers to a group with a C3-C6 bond structure. 10 A divalent group with the same structure as the cycloalkenyl group.
[0338] As used in this article, the term "C2-C" 10 "Heterocyclic alkenyl group" refers to a monovalent monocyclic group having at least one N, O, P, Si, Se, Ge, B, or S as a cyclizing atom, 2-10 carbon atoms, and at least one carbon-carbon double bond in its ring. The C2-C 10Non-limiting examples of heterocyclic alkenyl groups are 2,3-dihydrofuranyl and 2,3-dihydrothiophenyl groups. The term "C2-C" is used herein. 10 "Heterocyclic alkenyl group" refers to a group with a C2-C... 10 Divalent groups with the same structure as heterocyclic alkenyl groups.
[0339] As used in this article, the term "(C1-C" is similar to the term "(C1-C)" 10 "alkyl)carbazole group" refers to the group formed by C1-C2. 10 Carbazole group substituted with alkyl group.
[0340] As used in this article, the term "two (C1-C)" 10 "alkyl)'X' group" refers to a group consisting of two C1-C2 groups. 10 An 'X' group substituted with an alkyl group.
[0341] As used in this article, the term "C6-C" 60 "Aryl group" refers to a monovalent group having a carbocyclic aromatic system with 6-60 carbon atoms, and as used herein, "C6-C..." 60 "Arylene" refers to a divalent group that has a carbocyclic aromatic system with 6-60 carbon atoms. The C6-C... 60 Non-limiting examples of aryl groups include phenyl groups, naphthyl groups, anthracene groups, phenanthrene groups, pyrene groups, and... Basic group. When C6-C 60 aryl groups and C6-C 60 When each of the aryl groups comprises two or more rings, the rings may be fused together.
[0342] As used in this article, the term "C1-C" 60 "Heteroaryl group" refers to a monovalent group having a cyclic aromatic system having at least one N, O, P, Si, Se, Ge, B, or S as a cyclic atom in addition to 1-60 carbon atoms. The term "C1-C" is used herein. 60 "Hypoaryral group" refers to a divalent group having the following cyclic aromatic system: in addition to 1-60 carbon atoms, the cyclic aromatic system also has at least one N, O, P, Si, Se, Ge, B, or S as a cyclic atom. C1-C 60 Non-limiting examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl groups. When C1-C 60 heteroaryl groups and C1-C 60 When each of the heteroaryl groups comprises two or more rings, the rings may fused together.
[0343] As used in this article, the term "C6-C" 60 "Aryloxy group" indicates -OA 102 (where A) 102 For C6-C 60 (aryl group), and as used herein, the term C6-C 60 Aryl thio group represents -SA 103 (where A) 103 For C6-C 60 (aryl group).
[0344] As used herein, the term "monovalent nonaromatic fused polycyclic group" refers to a monovalent group (e.g., having 8-60 carbon atoms) that has two or more rings fused together, has only carbon atoms as cyclic atoms, and is not aromatic throughout its molecular structure. Examples of such monovalent nonaromatic fused polycyclic groups include fluorenyl groups. As used herein, the term "divalent nonaromatic fused polycyclic group" refers to a divalent group having the same structure as the monovalent nonaromatic fused polycyclic group.
[0345] As used herein, the term "monovalent nonaromatic fused heterocyclic group" refers to a monovalent group (e.g., having 2-60 carbon atoms) that has two or more rings fused together, has heteroatoms N, O, P, Si, Se, Ge, B, or S as cyclic atoms in addition to carbon atoms, and is not aromatic throughout its molecular structure. Non-limiting examples of such monovalent nonaromatic fused heterocyclic groups include carbazole groups. As used herein, the term "divalent nonaromatic fused heterocyclic group" refers to a divalent group having the same structure as the monovalent nonaromatic fused heterocyclic group.
[0346] As used in this article, the term "C5-C" 30 A "carbocyclic group" refers to a saturated or unsaturated cyclic group with only 5-30 carbon atoms as cyclic atoms. (C5-C) 30 The carbon ring group can be a monocyclic group or a polycyclic group.
[0347] As used in this article, the term "C1-C" 30 A "heterocyclic group" refers to a saturated or unsaturated cyclic group that has at least one heteroatom selected from N, O, P, Si, Se, Ge, B, or S as a cyclic atom in addition to 1-30 carbon atoms. (C1-C) 30 Heterocyclic groups can be monocyclic or polycyclic.
[0348] Replacement C5-C 30 Carbocyclic groups, substituted C1-C 30 Heterocyclic groups, substituted C1-C 60 Alkyl groups, substituted C2-C60 alkenyl groups, substituted C2-C 60 alkynyl group, substituted C1-C 60 alkoxy groups, substituted C3-C 10 Cycloalkyl groups, substituted C2-C 10 Heterocyclic alkyl groups, substituted C3-C 10 Cycloalkenyl groups, substituted C2-C 10 Heterocyclic alkenyl groups, substituted C6-C 60 aryl group, substituted C6-C 60 aryloxy groups, substituted C6-C 60 aryl thiols, substituted C1-C 60 The substituents of heteroaryl groups, substituted monovalent non-aromatic fused polycyclic groups, and substituted monovalent non-aromatic fused heterocyclic groups can be:
[0349] Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidine group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl groups, C2-C 60 alkenyl groups, C2-C 60 alkynyl group, or C1-C 60 Alkoxy group;
[0350] Each of the following C1-C is replaced: 60 Alkyl groups, C2-C 60 alkenyl groups, C2-C 60 alkynyl group, or C1-C 60 Alkoxy groups: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl groups, cyano groups, nitro groups, amino groups, amidine groups, hydrazine groups, hydrazone groups, carboxylic acid groups or their salts, sulfonic acid groups or their salts, phosphate groups or their salts, C3-C 10 Cycloalkyl groups, C2-C 10 Heterocyclic alkyl groups, C3-C 10 Cycloalkenyl groups, C2-C 10 Heterocyclic alkenyl groups, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 aryl thiols, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -N(Q) 11 (Q)12 ), -Si(Q 13 (Q) 14 (Q) 15 -B(Q) 16 (Q) 17 -P(=O)(Q) 18 (Q) 19 ), or any combination thereof;
[0351] C3-C 10 Cycloalkyl groups, C2-C 10 Heterocyclic alkyl groups, C3-C 10 Cycloalkenyl groups, C2-C 10 Heterocyclic alkenyl groups, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 aryl thiols, C1-C 60 The heteroaryl group, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heterocyclic group, each unsubstituted or substituted with the following: deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidoyl group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl groups, C2-C 60 alkenyl groups, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C3-C 10 Cycloalkyl groups, C2-C 10 Heterocyclic alkyl groups, C3-C 10 Cycloalkenyl groups, C2-C 10 Heterocyclic alkenyl groups, C6-C 60 aryl group, C6-C 60 aryloxy group, C6-C 60 aryl thiols, C1-C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heterocyclic groups, -N(Q) 21 (Q) 22 ), -Si(Q 23 (Q) 24 (Q) 25 -B(Q) 26 (Q) 27 -P(=O)(Q) 28 (Q) 29 ), or any combination thereof;
[0352] -N(Q31 (Q) 32 ), -Si(Q 33 (Q) 34 (Q) 35 -B(Q) 36 (Q) 37 ) or -P(=O)(Q 38 (Q) 39 );or
[0353] Any combination thereof.
[0354] In this specification, Q1 to Q9, Q 11 To Q 19 Q 21 To Q 29 , and Q 31 To Q 39 Each of these can independently be hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl group; cyano group; nitro group; amidine group; hydrazine group; hydrazone group; carboxylic acid group or its salt; sulfonic acid group or its salt; phosphate group or its salt; unsubstituted or deuterated, C1-C 60 alkyl groups, C6-C 60 aryl groups, or any combination thereof, substituted C1-C 60 Alkyl group; C2-C 60 alkenyl group; C2-C 60 alkynyl group; C1-C 60 Alkoxy group; C3-C 10 Cycloalkyl groups; C2-C 10 Heterocyclic alkyl groups; C3-C 10 Cycloalkenyl group; C2-C 10 Heterocyclic alkenyl groups; unsubstituted or deuterated, C1-C 60 alkyl groups, C6-C 60 aryl groups, or any combination thereof, substituted C6-C 60 Aryl group; C6-C 60 aryloxy group; C6-C 60 Aryl thioyl group; C1-C 60 Heteroaryl groups; monovalent non-aromatic fused polycyclic groups; or monovalent non-aromatic fused heterocyclic groups.
[0355] In the following description, the compounds and organic light-emitting devices according to the embodiments are described in detail with reference to the synthesis examples and examples, but are not limited thereto. The phrase "using 'B' instead of 'A'" used in describing the synthesis examples means that the amount of 'A' used is the same as the amount of 'B' used in terms of molar equivalents.
[0356] Example
[0357] Synthesis Example 1 (Synthesis of Compounds 3-348)
[0358]
[0359] Synthesis of ligand 3-348C
[0360] 2.1 g (0.005 mol, 1.2 equivalents) of intermediate 3-348B, 2.2 g (0.004 mol, 1 equivalent) of intermediate 3-348A (i.e., 2-(1-([1,1'-biphenyl]-2-yl)-4-bromo-1H-benzo[d]imidazol-2-yl)-4,6-di-tert-butylphenol), 1.2 g (0.001 mol, 0.07 equivalents) of tetra(triphenylphosphine)palladium(0), and 1.7 g (0.012 mol, 3 equivalents) of potassium carbonate were dissolved in 20 mL of a solvent in which tetrahydrofuran (THF) and distilled water (H2O) were mixed in a 3:1 volume ratio, and the mixture was refluxed for 12 hours. The resulting product was cooled to room temperature, and the precipitate was filtered off. The resulting filtrate was washed with ethyl acetate (EA) / H₂O and then subjected to column chromatography (with the volume fraction of EA / hexane (Hex) increased to between 20% and 35%) to obtain 2.0 g (yield: 72%) of ligand 3-348C. The product was identified by mass spectrometry and HPLC.
[0361] HRMS (MALDI): For C 54 H 53 Calculated value of N3O: m / z 759.4189, measured value: 759.4182
[0362] Synthesis of compound 3-348
[0363] 2.0 g (2.38 mmol) of ligand 3-348C and 0.98 g (2.38 mmol, 1.0 equivalent) of K₂PtCl₄ were dissolved in 80 mL of a solvent consisting of 60 mL of acetic acid (AcOH) and 20 mL of H₂O, and the mixture was refluxed for 16 hours. The resulting product was cooled to room temperature, and the precipitate was filtered and redissolved in dichloromethane (MC). The resulting filtrate was washed with H₂O and then subjected to column chromatography (MC 40%, EA 1%, Hex 59%) to give 1.1 g of compound 3-348 (purity: 99% or higher, actual yield: 71%). The product was identified by mass spectrometry and HPLC.
[0364] HRMS (MALDI): For C 54 H 51 Calculated value of N3OPt: m / z 952.3680, measured value: 952.3678
[0365] Synthesis Example 2 (Synthesis of Compound 3-583)
[0366]
[0367] Synthesis of ligand 3-583C
[0368] 2.2 g (0.005 mol, 1.2 equivalents) of intermediate 3-583B, 2.4 g (0.004 mol, 1 equivalent) of intermediate 3-583A (i.e., 2-(4-bromo-1-(5-(tert-butyl)-[1,1'-biphenyl]-2-yl)-1H-benzo[d]imidazol-2-yl)-4,6-di-tert-butylphenol), 1.2 g (0.001 mol, 0.07 equivalents) of tetra(triphenylphosphine)palladium(0), and 2.0 g (0.015 mol, 3.7 equivalents) of potassium carbonate were dissolved in 80 mL of a solvent in which THF and distilled water (H2O) were mixed in a 3:1 volume ratio, and the mixture was refluxed for 12 hours. The resulting product was cooled to room temperature, and the precipitate was filtered off. The resulting filtrate was washed with EA / H2O and then subjected to column chromatography (eluting with a gradient of EA / Hex 20%-35%) to obtain 2.2 g (yield: 68%) of ligand 3-583C. The product was identified by mass spectrometry and HPLC.
[0369] HRMS (MALDI): For C 59 H 60 Calculated value of D3N3O: m / z 832.5159, measured value: 832.5161
[0370] Synthesis of compound 3-583
[0371] 2.2 g (2.26 mmol) of ligand 3-583C and 1.1 g (2.26 mmol, 1.0 equivalent) of K₂PtCl₄ were dissolved in 80 mL of a solvent containing 60 mL of AcOH and 20 mL of H₂O, and the mixture was refluxed for 16 hours. The resulting product was cooled to room temperature, and the precipitate was filtered and redissolved in MC. The resulting filtrate was washed with H₂O and then subjected to column chromatography (MC 40%, EA 1%, Hex 59%) to obtain 1.0 g of compound 3-583 (purity: 99% or higher, actual yield: 68%). The product was identified by mass spectrometry and HPLC.
[0372] HRMS (MALDI): For C 59 H 58 Calculated value of D3N3OPt: m / z 1025.4651, measured value: 1025.4653
[0373] Evaluation of Example 1
[0374] The HOMO levels of the following compounds were measured in air using a photoelectron spectrometer (e.g., AC3 manufactured by RIKEN KEIKI Co., Ltd.), and the results are shown in Table 1.
[0375] Table 1
[0376] compound Actual measurement results (eV) of HOMO energy level 3-348 -5.45 3-583 -5.43 H1-15 -5.95 H1-63 -6.07 H1-65 -6.12 H1-75 -6.07 HA1 -5.71 H2-2 -5.58 H2-71 -5.69 H2-72 -5.65 HA2 -5.35 HA3 -6.00
[0377]
[0378]
[0379] Example 1
[0380] The glass substrate on which the ITO electrode was fabricated was cut into 50mm × 50mm × 0.5mm dimensions, and ultrasonically treated with acetone, isopropanol, and pure water for 15 minutes each, followed by cleaning by exposure to ultraviolet light and ozone for 30 minutes. Next, F6-TCNNQ was deposited on the ITO electrode (i.e., the anode) of the glass substrate to form a... A hole injection layer of a certain thickness is formed, and HT3 is deposited on the hole injection layer to form a hole injection layer with a thickness of [missing information]. A first hole transport layer of thickness [thickness missing] is formed, on which F6-TCNNQ and HT3 are co-deposited at a weight ratio of 5:95 to form [missing information]. A second hole transport layer of a certain thickness, and HT3 deposited on the second hole transport layer to form a layer with... The thickness of the third hole transport layer.
[0381] Then, the host and dopant are co-deposited on the third hole transport layer at a weight ratio of 85:15 to form a structure with... The emitter layer has a thickness of [thickness value missing]. Here, a first compound (e.g., compound H1-63), a second compound (e.g., compound H2-2), and a third compound (e.g., compound H2-72) are used as the main body (where the weight ratio of the first compound, the second compound, and the third compound is 3:3.5:3.5), and compound 3-348 is used as the dopant.
[0382] Next, compounds ET1 and ET-D1 were co-deposited on the emitter layer at a weight ratio of 5:5 to form a structure with... An electron transport layer of a certain thickness is formed by depositing LiF on the electron transport layer to create an electron transport layer with... An electron-injected layer of a certain thickness is formed by vacuum deposition of Al onto the electron-injected layer to create a layer with [missing information]. The second electrode (i.e., the cathode) of a certain thickness was then used to fabricate an organic light-emitting device with the following structure: ITO / F6-TCNNQ F6-TCNNQ (5% by weight) Dopant (15% by weight) ET-D1 (50% by weight)
[0383]
[0384] Example 2 and Comparative Examples 1 to 4
[0385] The organic light-emitting device was fabricated in the same manner as in Example 1, except that the compounds listed in Table 2 were used as the host and dopant, respectively, in the formation of the emitting layer.
[0386] Evaluation of Example 2
[0387] The external quantum luminous efficiency (EQE), driving voltage, and lifetime (T) of the organic light-emitting devices fabricated according to Examples 1 and 2 and Comparative Examples 1 to 4 were evaluated. 95 The results are shown in Table 2. Here, an ammeter-voltmeter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used as the evaluation devices. Lifetime (T) 95 (At 16,000 nits) is obtained by evaluating the time (in hours) that elapses when the brightness is 95% of the initial brightness (100%). EQE and lifetime (T) 95 All are at 16,000 cd / m³ 2 Measured under the specified brightness.
[0388] Table 2
[0389]
[0390]
[0391]
[0392] Referring to Table 2, it is confirmed that, compared with the organic light-emitting devices of Comparative Examples 1 to 4, the organic light-emitting devices of Examples 1 and 2 have high EQE, low driving voltage and long lifetime characteristics.
[0393] Examples 3 and 4
[0394] Organic light-emitting devices were fabricated in the same manner as in Examples 1 and 2, except that compound 3-583 was used instead of compound 3-348 as a dopant in the formation of the emission layer.
[0395] Evaluation of Example 3
[0396] The EQE, driving voltage, and lifetime (T) of the organic light-emitting devices of Examples 3 and 4 were evaluated in the same manner as in Example 2. 95 The results are shown in Table 3.
[0397] Table 3
[0398]
[0399]
[0400] Referring to Table 3, it is confirmed that the organic light-emitting devices of Examples 3 and 4 have excellent EQE, excellent driving voltage, and excellent lifetime characteristics.
[0401] According to one or more embodiments, the composition has excellent electrical properties and excellent stability, and therefore, electronic devices including the composition, such as organic light-emitting devices, can have improved external quantum luminescence efficiency, improved driving voltage, and improved lifetime characteristics.
[0402] It should be understood that the embodiments described herein should be considered only in a descriptive sense and are not intended for limiting purposes. The descriptions of features or aspects in each embodiment should typically be considered applicable to other similar features or aspects in other embodiments.
[0403] Although one or more embodiments have been described with reference to the accompanying drawings, those skilled in the art will understand that various changes in form and detail may be made therein without departing from the spirit and scope of this disclosure as defined by the appended claims.
Claims
1. A composition comprising a Pt-containing organometallic compound, a first compound, a second compound, and a third compound. The composition does not include iridium. The Pt-containing organometallic compound, the first compound, the second compound, and the third compound are different from each other. The first compound includes at least one electron transport component. The second and third compounds do not contain metals. The absolute values of the HOMO energy levels of the second compound and the third compound are each between 5.30 eV and 5.85 eV. The absolute value of the HOMO energy level of the second compound differs from the absolute value of the HOMO energy level of the third compound by 0.01 eV to 0.30 eV. The HOMO levels of the second compound and the third compound were each measured in air using a photoelectron spectroscopy instrument. The Pt-containing organometallic compound is a compound represented by formula 1-1: , in, In Equation 1-1, M is Pt, Y1 is O or S, Y2 to Y4 are chemical bonds, X1 and X3 are C, X2 and X4 are N, and T1 and T3 are single bonds. X 11 For C-[(L 11 ) b11 -(R 11 ) c11 ], X 12 For C-[(L 12 ) b12 -(R 12 ) c12 ], X 13 For C-[(L 13 ) b13 -(R 13 ) c13 ], and X 14 For C-[(L 14 ) b14 -(R 14 ) c14 ], X 21 For C-[(L 21 ) b21 -(R 21 ) c21 ], X 22 For C-[(L 22 ) b22 -(R 22 ) c22 ], and X 23 For C-[(L 23 ) b23 -(R 23 ) c23 ], X 29 For N-[(L 29 ) b29 -(R 29 ) c29 ], X 31 For C-[(L 31 ) b31 -(R 31 ) c31 ], X 32 For C-[(L 32 ) b32 -(R 32 ) c32 ], and X 33 For C-[(L 33 ) b33 -(R 33 ) c33 ], X 41 For C-[(L 41 ) b41 -(R 41 ) c41 X 42 For C-[(L 42 ) b42 -(R 42 ) c42 ], X 43 For C-[(L 43 ) b43 -(R 43 ) c43 ], and X 44 For C-[(L 44 ) b44 -(R 44 ) c44 ], L 11 To L 14 L 21 To L 23 L 31 To L 33 and L 41 To L 44 Each is an independent single bond, L 29 It is a phenyl group. b11 to b14, b21 to b23, b29, b31 to b33, and b41 to b44 are each independently 1. R 11 To R 14 R 21 To R 23 and R 31 To R 33 Each independently is: Hydrogen, deuterium, or C1-C 20 alkyl groups; or C1-C replaced as follows 20 Alkyl groups: deuterium, -CD3, -CD2H, -CDH2, C1-C 10 alkyl groups, or any combination thereof, R 29 and R 41 To R 44 Each independently is: Hydrogen, deuterium, or C1-C 20 alkyl groups; C1-C replaced as follows 20 Alkyl groups: deuterium, -CD3, -CD2H, -CDH2, C1-C 10 alkyl groups, or any combination thereof; or phenyl group or (C1-C) 20 Alkyl)phenyl groups, each unsubstituted or substituted with: deuterium, -CD3, -CD2H, -CDH2, C1-C 20 alkyl groups, or any combination thereof, c11 to c14, c21 to c23, c31 to c33, and c41 to c44 are each independently 1, and c29 is an integer from 1 to 10; The first compound is the compound represented by Formula 2: Formula 2 In Equation 2, Het1 is a group represented by formula 2-1: , L 61 It is a phenyl group. R 61 for: Hydrogen, deuterium, or C1-C 20 alkyl groups; C1-C replaced as follows 20 Alkyl groups: deuterium, -CD3, -CD2H, -CDH2, C1-C 10 alkyl groups, or any combination thereof; or phenyl group, (C1-C 20 The alkyl)phenyl group or carbazole group is unsubstituted or substituted with the following: deuterium, -CD3, -CD2H, -CDH2, C1-C 20 alkyl groups, or any combination thereof, R 62 The carbazole group is either unsubstituted or substituted with the following groups: deuterium, -CD3, -CD2H, -CDH2, C1-C. 20 alkyl groups, or any combination thereof, b61 is 1. a61 is an integer from 0 to 20, and a62 is 1. n is 2; The second compound and the third compound are each independently represented by formula 3-1: Equation 3-1 In Equation 3-1, Depend on The group represented is the group represented by formula 3(1): , X 71 For N-(L 75 ) b75 -(R 75 ) a75 , m is 2, L 75 It is a phenyl group, L 79 It is a single key. b75 is 2. R 71 R 72 and R 75 Each independently is: Hydrogen, deuterium, -F, or C1-C 20 alkyl groups; or C1-C replaced as follows 20 Alkyl groups: deuterium, -CD3, -CD2H, -CDH2, C1-C 10 alkyl groups, or any combination thereof, a71, a72, and a75 are each independent integers from 0 to 20.
2. The composition of claim 1, wherein... The absolute values of the HOMO energy levels of the Pt-containing organometallic compounds are 5.25 eV to 5.55 eV, and The HOMO levels of the Pt-containing organometallic compounds were measured in air using a photoelectron spectroscopy instrument.
3. The composition of claim 1, wherein... At least one of the second compound and the third compound does not include an electron transport component.
4. The composition of claim 1, wherein... The composition satisfies the following equations 1 and 2: Equation 1 HOMO (H2) > HOMO (D) Equation 2 HOMO (H3) > HOMO (D), in, In equations 1 and 2, HOMO(H2) is the absolute value of the HOMO energy level of the second compound. HOMO(H3) is the absolute value of the HOMO energy level of the third compound. HOMO(D) is the absolute value of the HOMO energy level of the Pt-containing organometallic compound, and The HOMO levels of the Pt-containing organometallic compounds were measured in air using a photoelectron spectroscopy instrument.
5. The composition of claim 4, wherein... The absolute value of the HOMO energy level of the second compound differs from the absolute value of the HOMO energy level of the Pt-containing organometallic compound by 0.05 eV to 0.6 eV. The absolute value of the HOMO energy level of the third compound is 0.05 eV to 0.6 eV different from the absolute value of the HOMO energy level of the Pt-containing organometallic compound.
6. Organic light-emitting devices, including: First electrode; Second electrode; as well as An organic layer comprising an emission layer is disposed between the first electrode and the second electrode. The organic layer thereof comprises the composition as described in any one of claims 1-5.
7. The organic light-emitting device as claimed in claim 6, wherein... The emitting layer comprises the composition.
8. The organic light-emitting device as claimed in claim 7, wherein... The emitter layer includes a dopant and a host. The dopant includes the Pt-containing organometallic compound of the composition, and The main body includes the first compound of the composition, the second compound of the composition, and the third compound of the composition.
9. The organic light-emitting device as claimed in claim 8, wherein... The emitting layer emits green light.