CN112771031A - Compound, light-emitting material, delayed phosphor, organic light-emitting element, oxygen sensor, method for designing molecule, and program - Google Patents
Compound, light-emitting material, delayed phosphor, organic light-emitting element, oxygen sensor, method for designing molecule, and program Download PDFInfo
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- CN112771031A CN112771031A CN201980062456.1A CN201980062456A CN112771031A CN 112771031 A CN112771031 A CN 112771031A CN 201980062456 A CN201980062456 A CN 201980062456A CN 112771031 A CN112771031 A CN 112771031A
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- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
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- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical class C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
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- 238000003780 insertion Methods 0.000 description 1
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- 229910052740 iodine Inorganic materials 0.000 description 1
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- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
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- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
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- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
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- 150000003852 triazoles Chemical group 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
Images
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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Abstract
The compound in which the local excited triplet level E (3LE), the charge transfer type lowest excited singlet level E (1CT), and the charge transfer type lowest excited triplet level E (3CT) are all within the energy width range of 0.3eV is useful as a light-emitting material.
Description
Technical Field
The present invention relates to a compound useful as a light-emitting material and an organic light-emitting element using the same. The present invention also relates to an oxygen sensor using the compound. Furthermore, the present invention relates to a method and a program for designing a molecule.
Background
Studies are actively being made to improve the light emission efficiency of organic light emitting elements such as organic electroluminescent elements (organic EL elements). In particular, many efforts have been made to improve the light emission efficiency by newly developing and combining an electron transport material, a hole transport material, a light emitting material, and the like that constitute an organic electroluminescent element. Among them, studies have been also found on an organic electroluminescent element using a compound having a donor group and an acceptor group (a D-a type compound) as a light-emitting material.
For example, non-patent document 1 reports that a compound represented by the following formula is used in an organic EL element in a light-emitting material. In the following formulae, the diphenyltriazinyl group corresponds to an acceptor group, and the group represented by R corresponds to a donor group. Further, non-patent document 1 shows that when a compound in which R is a phenothiazinyl group is used, external quantum efficiency of 10% is achieved.
[ chemical formula 1]
Prior art documents
Non-patent document
Non-patent document 1: J.am.chem.Soc.2017,139,4894-4900
Disclosure of Invention
Technical problem to be solved by the invention
As described above, non-patent document 1 describes that a compound having a structure in which the 4-position and the 5-position of 9, 9-dimethylxanthene (the ortho position of each benzene ring with respect to the oxygen group) are substituted with a donor group and an acceptor group, respectively, is used as a light-emitting material for an organic EL element. However, the external quantum efficiency achieved by using these compounds is at most 10%, which cannot be said to be very satisfactory. Further, many compounds proposed as light-emitting materials include the above compounds, and their luminous efficiency is lowered in a high current density region, and further improvement of characteristics is required for realizing practical organic EL devices.
In contrast, the present inventors have conducted studies on a group of compounds of a-D type having a core skeleton of a condensed polycyclic structure having a structure in which benzene rings are condensed on both sides of one ring (central ring), and synthesized compounds by variously changing the structure of the core skeleton or the substitution positions of a donor group and an acceptor group in the core skeleton, and evaluated the characteristics thereof, and have found for the first time that a group of compounds having a structure in which a substituted or unsubstituted methylene group is provided on the ring at the center of the core skeleton and the donor group and the acceptor group are substituted on the benzene rings at both sides thereof at the positions ortho to the methylene group exhibits high luminous efficiency and is effective as a light-emitting material, and have decided to conduct further studies. As described above, non-patent document 1 describes that a D-a type compound having 9, 9-dimethylxanthene as a core skeleton is used for a light-emitting material. However, the compounds described in non-patent document 1 all have donor groups and acceptor groups at the 4-and 5-positions (ortho positions to the oxy group on the benzene rings) of 9, 9-dimethylxanthene, and non-patent document 1 does not describe any compound in which donor groups and acceptor groups are introduced at other positions. Therefore, from non-patent document 1, it is difficult to predict that a compound having a structure in which a substituted or unsubstituted methylene group is present in the central ring of the core skeleton and a donor group or an acceptor group is substituted in the ortho position to the methylene group of the benzene rings on both sides thereof, exhibits high luminous efficiency.
Under such circumstances, the present inventors have further studied the effectiveness of a compound having a structure in which a substituted or unsubstituted methylene group is provided in the central ring of the core skeleton and a donor group and an acceptor group are substituted in the ortho position to the methylene group of the benzene rings on both sides thereof, as a light-emitting material, and have repeatedly studied aiming at finding a compound having excellent light-emitting characteristics. Further, intensive studies have been made for the purpose of deriving a general formula of a compound useful as a light-emitting material and popularizing the structure of an organic light-emitting element having high light-emitting efficiency.
Means for solving the technical problem
As a result of intensive studies, the present inventors have found that a compound in which the local excited triplet level E (3LE), the charge transfer type lowest excited singlet level E (1CT), and the charge transfer type lowest excited triplet level E (3CT) satisfy a specific relationship has excellent properties as a light-emitting material. Further, it has been found that such a compound group contains a compound useful as a delayed fluorescence material, and it has been found that an organic light-emitting element having high emission efficiency can be provided at low cost. The present invention has been proposed based on these findings, and specifically has the following structure.
[1] A compound in which a local excited triplet level E (3LE), a charge-moving lowest excited singlet level E (1CT) and a charge-moving lowest excited triplet level E (3CT) are within an energy width of 0.3eV in the individual compound.
[2]According to [1]The compound of (1), wherein an inverse system cross-over rate constant k between excited singlet state and triplet stateRISCIs 1 × 106s-1The above.
[3]According to [1]The compound of (1), wherein an inverse system cross-over rate constant k between excited singlet state and triplet stateRISCIs 1 × 107s-1The above.
[4] The compound according to any one of [1] to [3], which has a structure in which a donor group and an acceptor group are bonded to a ring skeleton, respectively.
[5] The compound according to [4], wherein a distance between an atom constituting the donor group and bonded to the ring skeleton and an atom constituting the acceptor group and bonded to the ring skeleton is structurally fixed.
[6] The compound according to any one of [1] to [5], which is composed of only a carbon atom, a hydrogen atom and a nitrogen atom.
[7] A compound represented by the following general formula (1) wherein,
[ chemical formula 2]
General formula (1)
[ in the general formula (1), R1～R6Each independently represents a hydrogen atom or a substituent. R7And R8Each independently represents a hydrogen atom or an alkyl group or R7And R8Bonded to each other to form a ring structure. L represents a single bond or a linking group, or R7And L are bonded to each other to form a cyclic structure, or R8And L are bonded to each other to form a ring structure. D represents a donor group and A represents an acceptor group.]
[8] The compound according to [7], wherein D and A in the general formula (1) each have an aromatic ring.
[9] The compound according to [8], wherein D and A in the general formula (1) are both aromatic rings and are bonded to the ring skeleton of the general formula (1).
[10]According to [7]To [9]]The compound according to any one of the above formulae (1), wherein R is represented by the general formula7Bonded to L to form a ring structure.
[11]According to [7]To [10 ]]The compound according to any one of the above general formulae (1), wherein L is a single bond, -O-, -S-, -N (R)81)-、-C(R82)(R83) -or-Si (R)84)(R85) -, said R81～R85Each independently represents a hydrogen atom or a substituent or with R7Or R8Bonded to form a ring structure.
[12]According to [11]The compound of (1), wherein L in the general formula (1) is-N (R)81)-、-C(R82)(R83) -or-Si (R)84)(R85) -, said R81～R85Any of (1) and R7Or R8The cyclic structure formed by bonding includes a linking group having a linking chain length of 1 to 3 atoms.
[13]According to [12 ]]The compound of (1), wherein R81～R85And R7Or R8The cyclic structure formed by bonding comprises a 1, 2-phenylene structure.
[14] A light-emitting material comprising the compound according to any one of [1] to [13 ].
[15] A delayed phosphor comprising the compound according to any one of [1] to [13 ].
[16] An organic light-emitting element comprising the compound according to any one of [1] to [13 ].
[17] The organic light-emitting element according to [16], which is an organic electroluminescent element.
[18] The organic light-emitting element according to [16] or [17], which comprises the compound in a light-emitting layer.
[19] The organic light-emitting element according to [18], wherein the light-emitting layer contains a host material.
[20] The organic light-emitting element according to [19], wherein the local excited triplet level E (3LE), the charge-transporting lowest excited singlet level E (1CT), and the charge-transporting lowest excited triplet level E (3CT) of the light-emitting layer containing the host material and the compound are each in a range of an energy width of 0.3 eV.
[21] An oxygen sensor comprising the compound according to any one of [1] to [13 ].
[22] Use of a compound having a local excited triplet level E (3LE), a charge-transporting lowest excited singlet level E (1CT), and a charge-transporting lowest excited triplet level E (3CT) each in the range of an energy width of 0.3eV as a light-emitting material.
[23] Use of a composition as a light-emitting material, wherein the composition comprises a compound having a local excited triplet level E (3LE), a charge-moving lowest excited singlet level E (1CT), and a charge-moving lowest excited triplet level E (3CT) each in the range of an energy width of 0.3eV, and does not comprise a solvent and a host material.
[24] A method of designing a molecule having a donor group and an acceptor group,
the distance between the donor group and the acceptor group is determined so that the local excited triplet level E (3LE), the charge-transporting lowest excited singlet level E (1CT) and the charge-transporting lowest excited triplet level E (3CT) are all within the energy width of 0.3eV, and the donor group and the acceptor group are structurally fixed so as not to vary the distance.
[25] A program which carries out the method of [24] for designing a molecule.
Effects of the invention
The compound of the present invention has excellent light-emitting characteristics and is useful as a light-emitting material. Also, a substance that emits delayed fluorescence is contained in the compound of the present invention. An organic light-emitting element using the compound of the present invention as a light-emitting material can achieve high light-emitting efficiency. Further, when the compound of the present invention is used as an oxygen sensor, oxygen can be detected with high sensitivity. Further, a molecule having the above-described characteristics can be easily designed by using the method or program for designing a molecule of the present invention.
Drawings
FIG. 1 is a schematic diagram showing the distribution of HOMO and LUMO in Compound 1.
Fig. 2 is a schematic cross-sectional view showing an example of the layer structure of the organic electroluminescent element.
FIG. 3 is an ultraviolet-visible absorption spectrum of a toluene solution of Compound 1.
FIG. 4 shows the luminescence spectrum of a toluene solution of Compound 1.
Fig. 5 is a transient decay curve of luminescence of a thin film composed of compound 1.
Fig. 6 is a graph showing current density-voltage-luminance characteristics of an organic electroluminescent element using compound 1.
Detailed Description
The present invention will be described in detail below. The following description of the constituent elements may be based on a representative embodiment or specific example of the present invention, but the present invention is not limited to such an embodiment or specific example. In the present specification, the numerical range expressed by the term "to" means a range including the numerical values described before and after the term "to" as the lower limit value and the upper limit value. And, used in the present inventionThe isotope type of hydrogen atoms in the molecule of the compound is not particularly limited, and for example, all hydrogen atoms in the molecule may be hydrogen atoms1H may be partially or wholly represented by2H (deuterium) D).
[ Compound and molecular design method of the present invention defined by energy level ]
The compounds of the invention are the following: the local excited triplet level E (3LE), the charge transfer type lowest excited singlet level E (1CT), and the charge transfer type lowest excited triplet level E (3CT) are within an energy width of 0.3eV in each individual compound.
The compound of the present invention is characterized in that the 3 levels are within 0.3eV when the compound is present alone. When the compound is in a solution state in which the compound is dissolved in a solvent, the charge transfer type lowest excited singlet level E (1CT) and the charge transfer type lowest excited triplet level E (3CT) are relatively greatly changed by the solvent. When the host material is present in a mixed state, the host material relatively greatly fluctuates. The compound of the present invention has a local excited triplet level E (3LE), a charge-transfer lowest excited singlet level E (1CT), and a charge-transfer lowest excited triplet level E (3CT) within an energy width range of 0.3eV in the absence of such other materials as a solvent and a host material.
The compound in which 3 energy levels are limited to the energy width range of 0.3eV in the absence of other materials such as a solvent and a host material can be provided by controlling the positional relationship of the structure of the donor group and the acceptor group present in the compound. Regarding such a structural positional relationship, it is possible to provide by the molecular design method of the present invention, and it is possible to design a compound having a specific structure by this method.
The method for designing a molecule of the present invention is a method for designing a molecule having a donor group and an acceptor group, wherein the distance between the donor group and the acceptor group is determined so that each of a local excited triplet level E (3LE), a charge-transporting lowest excited singlet level E (1CT) and a charge-transporting lowest excited triplet level E (3CT) is within an energy width of 0.3eV, and the donor group and the acceptor group are structurally fixed so as not to vary the distance. The local excited triplet level E (3LE), the charge transfer type lowest excited singlet level E (1CT), and the charge transfer type lowest excited triplet level E (3CT) can be determined by calculation. For the calculation, an optimized structure based on DFT (Density Functional Theory) was employed and can be performed by LC- ω PBE method (Sun, H.; Zhong, C.; Bredas, J.L.J.chem.Theory.Comp.2015, 11,3851).
In carrying out the molecular design method of the present invention, the measured value can also be used as the energy level. As described later, the charge transfer type lowest excited singlet level E (1CT) and the charge transfer type lowest excited triplet level E (3CT) are obtained by measuring a fluorescence spectrum and a phosphorescence spectrum, respectively. The local excited triplet level E (3LE) is obtained by measuring the transient attenuation spectrum while changing the temperature, determining the activation energy for intersystem crossing and the activation energy for reverse intersystem crossing between the excited singlet state and the triplet state, and calculating in consideration of E (1CT) and E (3 CT). When there is a difference between the actually measured value of the energy level of the compound actually present and the calculated energy level of the compound, the accuracy of calculation of the energy level of the designed molecule can be improved by correcting the calculated value of the other molecular structure based on the difference. The calculation or correction of the molecular design method of the present invention can be performed by setting a program in advance and executing the program. The program may be stored in a recording medium and stored/used or operated by a computer. Also, design accuracy can be improved in combination with artificial intelligence or by using a deep learning function.
Examples of the compound of the present invention in which the local excited triplet level E (3LE), the charge transfer type lowest excited singlet level E (1CT), and the charge transfer type lowest excited triplet level E (3CT) are within the energy width of 0.3eV in each of the individual compounds include the compounds of the examples described below and the compounds represented by the general formula (1).
The compounds of the present invention are preferably compounds that structurally immobilize the donor and acceptor groups. When the distance between the donor group and the acceptor group is increased, the charge transfer type lowest excited singlet level E (1CT) and the charge transfer type lowest excited triplet level E (3CT) tend to be increased. On the other hand, the local excited triplet level E (3LE) is hardly affected by the distance between the donor group and the acceptor group. Thus, it is desirable that the donor group and the acceptor group be present at an appropriate distance and that the distance be maintained. Thus, the compounds of the present invention preferably structurally fix the donor and acceptor groups in place.
In order to form a structurally fixed state, the donor group and the acceptor group are preferably bonded to or embedded in a structurally invariant backbone structure. The skeletal structure described herein is preferably a structurally invariant ring structure. The term "unchanged structure" as used herein means that the position of a skeleton-constituting atom (relative position to other skeleton-constituting atoms) cannot be changed unless a covalent bond is cleaved. Examples of the skeleton include a bicyclic skeleton, tricyclic skeleton, and cage skeleton, all of which have no structural change. Examples of the structure in which the donor group and the acceptor group are embedded in the skeleton structure include a structure in which a partial skeleton structure 1(S1), a donor group (D), a partial skeleton structure 2(S2), and an acceptor group (a) are connected in a cyclic form as described below to fix the positional relationship between the donor group and the acceptor group in the molecule.
[ chemical formula 3]
In addition, with regard to the explanation and specific examples of the donor group and the acceptor group of the compound of the present invention, reference can be made to the explanation and specific examples of the donor group and the acceptor group in the explanation of the general formula (1) described later.
The donor group and the acceptor group of the compound of the present invention preferably each have an aromatic ring (including both aromatic rings and heteroaromatic rings).
In the compound of the present invention, the local excited triplet level E (3LE), the charge-transporting lowest excited singlet level E (1CT) and the charge-transporting lowest excited triplet level E (3CT) are preferably within an energy width of 0.200eV, more preferably within an energy width of 0.150eV, still more preferably within an energy width of 0.100eV, still more preferably within an energy width of 0.075eV, and particularly preferably within an energy width of 0.050eV in each of the individual compounds.
In the compound of the present invention, the difference between the local excited triplet level E (3LE) and the charge transport type lowest excited triplet level E (3CT) is preferably within 0.200eV, more preferably within 0.150eV, still more preferably within 0.100eV, yet still more preferably within 0.075eV, and particularly preferably within 0.050 eV.
In the compound of the present invention, the difference between the local excited triplet level E (3LE) and the charge transport lowest excited singlet level E (1CT) is preferably within 0.200eV, more preferably within 0.100eV, still more preferably within 0.050eV, yet more preferably within 0.025eV, and particularly preferably within 0.010 eV.
In the compound of the present invention, the reverse intersystem crossing rate constant k between excited singlet state and triplet stateRISCPreferably 1X 106s-1Above, more preferably 3 × 106s-1Above, more preferably 6 × 106s-1Above, more preferably 1 × 107s-1The above. k is a radical ofRISCAnd the intersystem crossing rate constant k between excited singlet and triplet statesISCRatio of (k)RISC/kISC) Preferably 0.1 or more, more preferably 0.5 or more, further preferably 0.8 or more, and further preferably 1.0 or more. As a preferred embodiment, a case where the excited singlet state and the triplet state are the charge transfer type lowest excited singlet state (1CT) and the charge transfer type lowest excited triplet state (3CT), respectively, is exemplified, but the present invention is not limited thereto.
The distance between the donor group and the acceptor group in the compound of the present invention can be set to, for example, a distance between an atom constituting the donor group and an atom bonded to the skeleton structure and an atom constituting the acceptor group and an atom bonded to the skeleton structure. The distance between the atom constituting the donor group and the atom constituting the skeletal structure bond and the atom constituting the acceptor group and the atom constituting the skeletal structure bond can be selected, for example, from 2.4 to 5.5 angstroms, from 3.5 to 5.2 angstroms, from 4.5 to 4.9 angstroms, or from 4.6 to 4.8 angstroms. Furthermore, the thickness of the film can be selected from the range of 4.6 to 4.7 angstroms or from the range of 4.7 to 4.8 angstroms.
In the structure in the most stabilized state, it is preferable that the inclination angle formed by the bonding direction in which the donor group and the skeleton structure are bonded and the bonding direction in which the acceptor group and the skeleton structure are bonded in the compound of the present invention is 1 ° or more. The tilt angle may be selected, for example, from the range of 5 ° or more, or from the range of 45 ° or less, or from the range of 30 ° or less, or from the range of 15 ° or less. For example, it can be selected within a range of 5 ° to 15 °. For example, the tilt angle of compound 1 described later is about 10 °.
In the compound of the present invention, the ratio [ epsilon (CT)/epsilon (pi) of pi type maximum molar absorption coefficient epsilon (pi) to charge transfer type maximum molar absorption coefficient epsilon (CT) is preferably 0.05 or less.
The compound of the present invention may be a compound containing no metal atom, a compound containing no sulfur atom, or a compound containing no oxygen atom. The compound of the present invention may be a compound composed of only carbon atoms, hydrogen atoms and nitrogen atoms.
[ Compound represented by the general formula (1) ]
The compound of the present invention has a structure represented by the following general formula (1).
[ chemical formula 4]
General formula (1)
In the general formula (1), R1～R6Each independently represents a hydrogen atom or a substituent. R7And R8Each independently represents a hydrogen atom or an alkyl group or R7And R8Bonded to each other to form a ring structure. L represents a single bond or a linking group, or R7And L are bonded to each other to form a cyclic structure, or R8And L are bonded to each other to form a ring structure. D represents a donor group and A represents an acceptor group.
At R1～R6The number of the group as a substituent in (1) is not particularly limited, and R1～R6All of (a) may also be unsubstituted (i.e., a hydrogen atom). At R1～R6When two or more of them are substituents, the substituents may be the same or different from each other.
R as formula (1)1～R6Examples of the substituent that can be used include a hydroxyl group, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkylthio group having 1 to 20 carbon atoms, an alkyl-substituted amino group having 1 to 20 carbon atoms, an acyl group having 2 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, a heteroaryl group having 3 to 40 carbon atoms, a diarylamino group having 12 to 40 carbon atoms, a carbazolyl group having 12 to 40 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkoxycarbonyl group having 2 to 10 carbon atoms, an alkylsulfonyl group having 1 to 10 carbon atoms, a haloalkyl group having 1 to 10 carbon atoms, an amide group, an alkylamide group having 2 to 10 carbon atoms, a trialkylsilyl group having 3 to 20 carbon atoms, a trialkylsilylalkyl group having 4 to 20 carbon atoms, a trialkylsilylalkenyl group having 5 to 20 carbon atoms, a haloalkenylamino group having 3 to 40, A C5-20 trialkylsilylkynyl group, a nitro group, and the like. In these embodiments, a group which can be further substituted with a substituent may be substituted. More preferred substituents are a halogen atom, a cyano group, a C1-20 substituted or unsubstituted alkyl group, a C1-20 alkoxy group, a C6-40 substituted or unsubstituted aryl group, a C3-40 substituted or unsubstituted heteroaryl group, a C12-40 substituted or unsubstituted diarylamino group, and a C12-40 substituted or unsubstituted heteroaryl groupThe carbazolyl group of (1). Further preferred substituents are a fluorine atom, a chlorine atom, a cyano group, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms, a substituted or unsubstituted dialkylamino group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 15 carbon atoms, and a substituted or unsubstituted heteroaryl group having 3 to 12 carbon atoms.
At R7And R8When represents a hydrogen atom or an alkyl group, R7And R8These two may be hydrogen atoms or these two may be alkyl groups, or one may be a hydrogen atom and the other may be an alkyl group. At R7And R8When the two are alkyl groups, the two alkyl groups may be the same as or different from each other. R7And R8The alkyl group in ((3) may be linear, branched or cyclic. The number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, and still more preferably 1 to 6. Examples thereof include methyl, ethyl, n-propyl, and isopropyl.
When L represents a linking group, the linking group is preferably a 2-valent linking group having a linking chain length of 1 atom. The connecting chain length as used herein refers to the number of atoms in the shortest atom chain of the atom chains connecting one connecting bond and the other connecting bond of the connecting group. For example, a linker chain length of 1,1, 2-phenylene when one atom has both a linker and another linker is a linker chain length of 2, 1, 3-phenylene is 3.
Specific examples of the linking group that can be used for L include-O-, -S-, -N (R)81)-、-C(R82)(R83) -or-Si (R)84)(R85) -the linking group represented. R81～R85Each independently represents a hydrogen atom or a substituent or with R7Or R8Bonded to form a ring structure. Herein, R is82And R83、R84And R85May be the same or different from each other. As R81Examples of the substituent that can be used include an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, and a carbon atomA sub-number of 3 to 40. As R82～R85Examples of the substituent which can be used include a hydroxyl group, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkylthio group having 1 to 20 carbon atoms, an alkyl-substituted amino group having 1 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, a heteroaryl group having 3 to 40 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkylamide group having 2 to 20 carbon atoms, an arylamide group having 7 to 21 carbon atoms, and a trialkylsilyl group having 3 to 20 carbon atoms.
R7And R8、R7And L, R8And L may be bonded to each other to form a ring structure. R7And R8、R7And L, R8And L may form a cyclic structure of R alone7And R8May also be R7And L and R8And L, or R alone7And L, may be R alone8And L. Of these, only R is preferred7And L or only R8And L. And, in R7And L are bonded to each other to form a cyclic structure, R8Preferably a hydrogen atom or a methyl group, in R8And L are bonded to each other to form a cyclic structure, R7Preferably a hydrogen atom or a methyl group.
With respect to R7And R8、R7And L, R8And L may be R7And R8、R7And L or R8The linking structure itself formed by bonding L and L to each other may be R7And R8、R7And L or R8And L are bonded to each other to form a cyclic structure together with the central ring (ring between two benzene rings) of the 3-ring structure in the general formula (1).
As R7And R8Examples of the cyclic structure formed by bonding to each other include a structure containing Z represented by the following general formula (2)1As in the ring of (1), C (R)7)(R8) C in (b) is a spiro ring having a spiro atom. With respect to R in the general formula (2)1～R8D, A, reference can be made to R in the above general formula (1)1～R8D, A, and preferred ranges.
[ chemical formula 5]
General formula (2)
Here, as containing Z1Examples of the ring (b) include alicyclic hydrocarbon rings having 3 to 20 carbon atoms and containing a spiro atom, and cyclopentane, cyclohexane, and cycloheptane rings are preferable.
And as R7And L, R8Examples of the cyclic structure formed by bonding L to each other include a structure in which R is bridged to the central ring of the 3-ring structure in the general formula (1)7And L or R8And L are bonded to each other to form a bridge ring. As R7Examples of the cyclic structure formed by bonding L and L to each other include a cyclic structure containing Z represented by the following general formula (3)2Of (2) a ring of (a). As R8Examples of the cyclic structure formed by bonding L and L to each other include a cyclic structure containing Z represented by the following general formula (4)3Of (2) a ring of (a). R in the general formula (3) and the general formula (4)1～R8D, A, reference can be made to R in the above general formula (1)1～R8D, A, and preferred ranges.
[ chemical formula 6]
General formula (3)
General formula (4)
Here, Z2And Z3The length of the connecting chain(s) is preferably 1 to 3 atoms. Z2Or Z3Preferably comprisesAt least one selected from the group consisting of a substituted or unsubstituted alkylene group, a substituted or unsubstituted arylene group, and a substituted or unsubstituted heteroarylene group, more preferably comprises a substituted or unsubstituted arylene group, and further preferably consists only of a substituted or unsubstituted arylene group.
At Z2And Z3When the alkylene group is contained, the alkylene group may be linear, branched or cyclic. The number of carbon atoms is preferably 1 to 20, more preferably 1 to 10, still more preferably 1 to 6, and still more preferably 1 to 3. For example, methylene, vinyl, propylene and the like can be exemplified.
At Z2And Z3When the aromatic hydrocarbon ring includes an arylene group, the aromatic hydrocarbon ring constituting the arylene group may be a single ring, a condensed ring in which 2 or more aromatic hydrocarbon rings are condensed, or a connection ring in which 2 or more aromatic hydrocarbon rings are connected. When two or more aromatic hydrocarbon rings are connected, they may be connected in a straight chain or in a branched chain. The number of carbon atoms of the aromatic hydrocarbon ring constituting the arylene group is preferably 6 to 22, more preferably 6 to 18, still more preferably 6 to 14, and still more preferably 6 to 10. Specific examples of the aromatic hydrocarbon ring constituting the arylene group include a benzene ring, a naphthalene ring, and a biphenyl ring.
At Z2And Z3When the heteroarylene group is contained, the aromatic heterocycle constituting the heteroarylene group may be a single ring, a condensed ring in which 1 or more heterocyclic rings and 1 or more aromatic hydrocarbon rings or aromatic heterocyclic rings are condensed, or a connecting ring in which 1 or more aromatic heterocyclic rings and 1 or more aromatic hydrocarbon rings or aromatic heterocyclic rings are connected. The number of carbon atoms of the aromatic heterocycle is preferably 5 to 22, more preferably 5 to 18, still more preferably 5 to 14, and still more preferably 5 to 10. The hetero atom constituting the aromatic heterocyclic ring is preferably a nitrogen atom. Specific examples of the aromatic heterocyclic ring include a pyridine ring, a pyridazine ring, a pyrimidine ring, a triazole ring, and a benzotriazole ring.
Among these, as Z2And Z3Preferred groups are those comprising a benzene ring, more preferably substituted or unsubstitutedThe group of phenylene group of (4) is more preferably a group containing an unsubstituted phenylene group. The phenylene group here may be any of 1, 2-phenylene, 1, 3-phenylene, and 1, 4-phenylene, but is preferably 1, 2-phenylene.
About being able to be at Z2And Z3The above-mentioned description and preferred ranges of the substituents substituted on the alkylene, arylene and heteroarylene groups contained in (1) can be referred to the above-mentioned R1～R6Description and preferred ranges of substituents that can be employed.
D represents a donor group. "donor group" in the present invention refers to a group that donates an electron to the group of bonded atoms of the donor group. For example, σ which can be selected from HammettpSubstituents with negative values.
Here, "Hammett's sigmapThe value "is a value proposed by l.p.hammett, which is a value that quantifies the influence of a substituent on the reaction rate or equilibrium of a para-substituted benzene derivative. Specifically, the following formula is established between the substituent in the para-substituted benzene derivative and the reaction rate constant or equilibrium constant:
log(k/k0)＝ρσp
or
log(k/k0)＝ρσp
A constant (. sigma.) specific to the substituent in (1)p). In the above formula, k represents the rate constant of the unsubstituted benzene derivative, and k0Denotes the rate constant of the substituted benzene derivative, K denotes the equilibrium constant of the unsubstituted benzene derivative, K0Represents an equilibrium constant of a substituted benzene derivative, and ρ represents a reaction constant determined by the kind and conditions of the reaction. Sigma of Hammett in relation to the present inventionpFor the description of the values "and the numerical values of the substituents, reference can be made to σ of Hansch, C.et.al., chem.Rev.,91, 165-195 (1991)pValue-related documentation.
As the donor group, an electron-donating substituent bonded through a hetero atom selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, and a phosphorus atom, or an aryl group exhibiting an electron-donating property is preferably used. The aryl group exhibiting electron donating property is usually a substituted aryl group, and is preferably an aryl group substituted with an electron donating substituent bonded through a hetero atom selected from the group consisting of a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom and a phosphorus atom, and more preferably an aryl group substituted with an electron donating substituent bonded through a nitrogen atom.
Also, the donor group preferably comprises a substituted or unsubstituted diarylamino structure, more preferably an aryl group substituted with a substituted or unsubstituted diarylamino group. Here, the "diarylamino structure" refers to two of a heteroaromatic ring structure in which diarylamino groups and aryl groups of diarylamino groups are connected to each other by a single bond or a connecting group to form a heterocyclic ring. The aromatic ring of each aryl group constituting the diarylamino structure and the aromatic ring of each aryl group constituting the diarylamino-substituted aryl group (each aryl group of the diarylamino group and the diarylamino-substituted aryl group) may be a single ring, a condensed ring in which 2 or more aromatic rings are condensed, or a connecting ring in which 2 or more aromatic rings are connected. When two or more aromatic rings are bonded, they may be bonded in a straight chain or in a branched chain. The number of carbon atoms in the aromatic ring of each aryl group constituting the diarylamino structure and the diarylamino-substituted aryl group is preferably 6 to 22, more preferably 6 to 18, even more preferably 6 to 14, and even more preferably 6 to 10. Specific examples of the aryl group include a phenyl group, a naphthyl group and a biphenyl group. With respect to the diarylamino structure and the explanation and preferable ranges of the substituents when the diarylamino-substituted aryl group has a substituent, the following R can be referred to11～R20Description and preferred ranges of substituents that can be employed. With respect to the description and preferred ranges of the linking group for linking aryl groups to each other when the diarylamino structure is the aforementioned heteroaromatic ring structure, reference can be made to R of the following general formula (5)15And R16Description and preferred ranges of the linking group when they are bonded to each other to form a linking group.
The donor group is preferably a group represented by the following general formula (5).
[ chemical formula 7]
General formula (5)
In the general formula (5), R11～R20Each independently represents a hydrogen atom or a substituent. In the general formula (5), R11～R20Each independently represents a hydrogen atom or a substituent. The number of substituents is not particularly limited, and R11～R20All of (a) may also be unsubstituted (i.e., a hydrogen atom). At R11～R20In the case where two or more of them are substituents, the substituents may be the same or different from each other. Denotes the bonding site.
As R11～R20Examples of the substituent that can be used include a hydroxyl group, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkylthio group having 1 to 20 carbon atoms, an alkyl-substituted amino group having 1 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, a heteroaryl group having 3 to 40 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkynyl group having 2 to 10 carbon atoms, an alkylamide group having 2 to 20 carbon atoms, an arylamide group having 7 to 21 carbon atoms, and a trialkylsilyl group having 3 to 20 carbon atoms. In these embodiments, a group which can be further substituted with a substituent may be substituted. More preferably, the substituent is an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkylthio group having 1 to 20 carbon atoms, an alkyl-substituted amino group having 1 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms or a heteroaryl group having 3 to 40 carbon atoms.
R11And R12、R12And R13、R13And R14、R14And R15、R15And R16、R16And R17、R17And R18、R18And R19、R19And R20May be bonded to each other to form a ring structure. The cyclic structure may be an aromatic ring or an aliphatic ring, or may be a structure containing a hetero atomThe cyclic structure may be a fused ring having 2 or more rings. The hetero atom described herein is preferably an atom selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom. Examples of the cyclic structure to be formed include a benzene ring, a naphthalene ring, a pyridine ring, a pyridazine ring, a pyrimidine ring, a pyrazine ring, a pyrrole ring, an imidazole ring, a pyrazole ring, an imidazoline ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, a cyclohexadiene ring, a cyclohexene ring, a cyclopentene ring, a cycloheptatriene ring, a cycloheptadiene ring, and a cycloheptene ring.
Among the groups represented by the general formula (5), R is preferable15And R16Non-bonded radicals, R15And R16Radicals or R bound to one another by single bonds15And R16Are bonded to each other to form a linking group having a chain length of 1 atom or 2 atoms. At R15And R16When R is bonded to each other to form a linking group having a connecting chain length of 1 atom or 2 atoms, R is15And R16The cyclic structure formed by bonding to each other is a 6-or 7-membered ring. As R15And R16Specific examples of the linking group formed by bonding to each other include-O-, -S-, -N (R)91) -or-C (R)92)(R93) -a linking group represented by or formed by bonding any two of these. Examples of the linking group formed by bonding any two of them include-O-C (R)92)(R93)-、-S-C(R92)(R93)-、-N(R91)-C(R92)(R93)-、-C(R92)(R93)-C(R94)(R95) Specific examples thereof include-O-CH2-、-O-C(CH3)2-、-S-CH2-、-S-C(CH3)2-、-N(CH3)-CH2-、-N(C6H5)-CH2-、-CH2CH2-、-C(CH3)2C(CH3)2-. Wherein R is91～R95Each independently represents a hydrogen atom or a substituent. With respect to R91Substituents which may be employed, R92～R95Can be adoptedThe description and preferred ranges of substituents can be referred to above for R, respectively81Substituents which may be employed, R82～R85Description and preferred ranges of substituents that can be employed.
Preferred examples of the group represented by the general formula (5) include groups represented by any of the following general formulae (6) to (10).
[ chemical formula 8-1]
General formula (6)
General formula (7)
General formula (8)
[ chemical formula 8-2]
General formula (9)
General formula (10)
In the general formulae (6) to (10), R21～R24、R27～R38、R41～R48、R51～R59、R71～R80Each independently represents a hydrogen atom or a substituent. With regard to the description and preferred ranges of substituents described herein, reference can be made to R as described above11～R20Description and preferred ranges of substituents that can be employed. R21～R24、R27～R38、R41～R48、R51～R59、R71～R80Also, each of the groups represented by the above general formulae (6) to (10) is preferably independent. Denotes the bonding site. R of the general formula (10)79And R80Preferably a substituted or unsubstituted alkyl group, more preferably a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. And R of the general formula (10)79And R80Also preferred is a substituted or unsubstituted aryl group, more preferred is a substituted or unsubstituted aryl group having 6 to 40 carbon atoms, still more preferred is a substituted or unsubstituted aryl group having 6 to 10 carbon atoms, and particularly preferred is a phenyl group. And R in the general formula (10)79And R80In the case of substituted or unsubstituted aryl groups, it is also preferred that the aryl groups are bonded to each other to form a cyclic structure. The number of the substituents in the general formulae (6) to (10) is not particularly limited. Also preferred is the case where all are unsubstituted (i.e., hydrogen atoms). When two or more substituents are present in each of the formulae (6) to (10), these substituents may be the same or different. When a substituent is present in the general formulae (6) to (10), the substituent is preferably R in the general formula (6)22～R24、R27～R29Any of them, more preferably R23And R28In the general formula (7), the substituent is preferably R32～R37In the general formula (8), the substituent is preferably R42～R47In the general formula (9), the substituent is preferably R52、R53、R56、R57、R59In the general formula (10), the substituent is preferably R72～R77、R79、R80Any one of them.
In the general formulae (6) to (10), R21And R22、R22And R23、R23And R24、R27And R28、R28And R29、R29And R30、R31And R32、R32And R33、R33And R34、R35And R36、R36And R37、R37And R38、R41And R42、R42And R43、R43And R44、R45And R46、R46And R47、R47And R48、R51And R52、R52And R53、R53And R54、R55And R56、R56And R57、R57And R58、R54And R59、R55And R59、R71And R72、R72And R73、R73And R74、R75And R76、R76And R77、R77And R78、R79And R80May be bonded to each other to form a ring structure. For the description and preferred examples of the cyclic structure, reference can be made to R in the above general formula (5)11And R12And the like, and preferred examples of the ring-like structure formed by bonding the two members to each other.
Among the compounds represented by the general formula (9), compounds represented by the following general formula (9') are particularly preferably contained.
[ chemical formula 9]
General formula (9')
In the general formula (9'), R51～R58、R61～R65Each independently represents a hydrogen atom or a substituent. R51And R52、R52And R53、R53And R54、R55And R56、R56And R57、R57And R58、R61And R62、R62And R63、R63And R64、R64And R65、R54And R61、R55And R65May be bonded to each other to form a ring structure. Denotes the bonding site.
A represents an acceptor group. An "acceptor group" in the present invention is a group that attracts electrons to the group of atoms to which the acceptor group is bonded. For example, σ which can be selected from HammettpA positive substituent.
The acceptor group is preferably a group represented by the following general formula (11) or a group having a partial structure represented by the following general formula (11).
[ chemical formula 10]
General formula (11)
In the general formula (11), A1～A5Each independently represents N or C (R)19)，R19Represents a hydrogen atom or a substituent. A. the1～A5At least one of them is preferably N, more preferably 1 to 3, and still more preferably 3. The group represented by the general formula (11) has a plurality of R19When a plurality of R19May be the same as or different from each other. As R19Examples of the substituent that can be used include an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, a cyano group, a halogen atom, a heteroaryl group having 5 to 40 carbon atoms, and the like, and an aryl group having 6 to 40 carbon atoms is preferable. Among these substituents, a group capable of being substituted by a substituent may be substituted.
A structure represented by the general formula (11) may be bonded to the linking group as an acceptor group. As the linking group at this time, a substituted or unsubstituted arylene group or a substituted or unsubstituted heteroarylene group is preferable. With regard to the description and preferred ranges for arylene or heteroarylene groups as described herein, reference can be made to the above R81～R85And R7Or R8Description of arylene and heteroarylene groups in the connecting structure formed by bonding, and preferable ranges thereof. With respect to the ability to introduce into arylene or heteroFor the description of the substituents of the arylene radicals and the preferred ranges, reference can be made to the abovementioned R19Description and preferred ranges of substituents that can be employed. The linking group is preferably a substituted or unsubstituted arylene group, more preferably a substituted or unsubstituted phenylene group. When the linking group is a substituted or unsubstituted phenylene group, the phenylene group may be any of 1, 2-phenylene, 1, 3-phenylene, and 1, 4-phenylene, but is preferably a 1, 4-phenylene group.
Specific examples of the acceptor group (A-1 to A-77) are shown below. Denotes the bonding site. The bonding position may be directly bonded to the benzene ring on the right side of the general formula (1) or may be bonded via a linking group. In the case where two are present in the molecule, one is attached and the other represents a hydrogen atom. Further, the hydrogen atom in the following specific examples may be substituted with a substituent.
[ chemical formula 11]
[ chemical formula 12]
[ chemical formula 13]
[ chemical formula 14]
[ chemical formula 15]
In the compound represented by the general formula (1), D is preferably a donor group containing a cyclic structure, and a is preferably an acceptor group containing a cyclic structure. Further, a and D preferably contain the same cyclic structure, and more preferably the same cyclic structure is a benzene ring.
In the compounds represented by the general formulae (1) to (4), R is1～R3May be a donor group, R4～R6May be an acceptor group. At this time, R1～R3May be the same donor group as D or a different donor group. And, R4～R6May be the same acceptor group as A or a different acceptor group.
The compound represented by the general formula (1) may be a compound composed of only carbon atoms, nitrogen atoms, and hydrogen atoms. For example, if the compound contains an atom such as a fluorine atom, a phosphorus atom, or a sulfur atom which is likely to generate polarity in the molecule, the solubility of the compound in an organic solvent may be low, but if the compound is composed of only a carbon atom, a nitrogen atom, and a hydrogen atom, the compound may exhibit good solubility in an organic solvent, and a film of the compound may be more easily formed by a coating method.
The compound represented by the general formula (1) is preferably such that the difference Δ E between the lowest excited singlet energy level S1 and the lowest excited triplet energy level T1 of 77KstSmall compounds. Specifically,. DELTA.EstPreferably 0.3eV or less, more preferably 0.2eV or less, still more preferably 0.1eV or less, and still more preferably 0.05eV or less.
The lowest excited singlet level S1 and the lowest excited triplet level T1 can be measured by the following methods, respectively.
(1) Lowest excited singlet energy level S1
A compound to be measured was deposited on an Si substrate to prepare a sample, and the fluorescence spectrum of the sample was measured at room temperature (300K). In the fluorescence spectrum, the vertical axis represents light emission, and the horizontal axis represents wavelength. A tangent is drawn to the fall of the emission spectrum on the short-wave side, and the wavelength value λ edge [ nm ] of the intersection of the tangent and the horizontal axis is determined. The wavelength value is converted into an energy value by a conversion equation shown below, and the obtained value is designated as S1.
Conversion formula: s1[ eV ] ═ 1239.85/λ edge
For the measurement of the luminescence spectrum, a nitrogen laser (LTB Lasertechnik Berlin GmbH, MNL200) was used as an excitation light source and a strip camera (Hamamatsu Photonics k.k. C4334) was used as a detector.
(2) Lowest excited triplet energy level T1
The sample having the same singlet energy S1 was cooled to 77[ K ], excitation light (337nm) was irradiated to the phosphorescence measurement sample, and the phosphorescence intensity was measured using a streak camera. A tangent is drawn to the rise on the short-wavelength side of the phosphorescence spectrum, and the wavelength value λ edge [ nm ] of the intersection of the tangent and the horizontal axis is obtained. The wavelength value was converted into an energy value by a conversion equation shown below, and the obtained value was taken as T1.
Conversion formula: t1[ eV ] ═ 1239.85/λ edge
The tangent to the rise on the short wavelength side of the phosphorescence spectrum is drawn as follows. Consider a tangent line at each point on a curve toward the long wavelength side when moving from the short wavelength side of the phosphorescence spectrum to the maximum value on the shortest wavelength side of the maximum values of the spectrum on the spectral curve. As the curve rises (i.e., as the vertical axis increases), the slope of the tangent line increases. The tangent drawn at the point where the slope value has the maximum value is defined as the tangent to the increase on the short-wavelength side of the phosphorescence spectrum.
In addition, the maximum point having a peak intensity of 10% or less of the maximum peak intensity of the spectrum does not include the maximum value on the shortest wavelength side, and a tangent drawn at a point closest to the maximum value on the shortest wavelength side and having a maximum slope value is defined as a tangent to an increase on the shortest wavelength side of the phosphorescence spectrum.
Examples of the compound represented by the general formula (1) include compounds having the following structures. The compounds represented by the general formula (1) that can be used in the present invention should not be construed as being limited to these specific examples.
[ chemical formula 16]
The molecular weight of the compound represented by the general formula (1) is preferably 1500 or less, more preferably 1200 or less, further preferably 1000 or less, and further preferably 800 or less, when an organic layer containing the compound represented by the general formula (1) is formed and used by a vapor deposition method, for example. The lower limit of the molecular weight is the smallest molecular weight that can be used in the general formula (1), and is preferably 20 or more molecular weight than the smallest molecular weight that can be used in the general formula (1).
The compound represented by the general formula (1) can be formed into a film by a coating method.
It is also possible to consider the application of the present invention in which a compound containing a plurality of structures represented by the general formula (1) in a molecule is used as a light-emitting material.
For example, a polymer obtained by pre-existing a polymerizable group in the structure represented by the general formula (1) and polymerizing the polymerizable group can be considered as a light-emitting material. Specifically, it is considered to prepare R in the general formula (1)1～R6L, D, A, by polymerizing the monomer containing a polymerizable functional group alone or together with other monomers, a polymer having a repeating unit is obtained, and the polymer is used as a light-emitting material. Alternatively, it is also conceivable to obtain a dimer or trimer by coupling compounds having a structure represented by general formula (1) with each other, and use these as a light-emitting material.
Examples of the polymer having a repeating unit having a structure represented by general formula (1) include polymers having a structure represented by general formula (12) or (13) below.
[ chemical formula 17]
In the general formula (12) or (13), Q represents a group containing the general formula (1)A group of the structure shown, L1And L2Represents a linking group. The number of carbon atoms of the linking group is preferably 0 to 20, more preferably 1 to 15, and further preferably 2 to 10. As the linking group, for example, a group having-X11-L11-a group of the structure represented. Here, X11Represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom. L is11Represents a linking group, preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted arylene group, more preferably a substituted or unsubstituted alkylene group or a substituted or unsubstituted phenylene group having 1 to 10 carbon atoms.
In the general formula (12) or (13), R101、R102、R103And R104Each independently represents a substituent. Preferably a C1-6 substituted or unsubstituted alkyl group, a C1-6 substituted or unsubstituted alkoxy group, a halogen atom, more preferably a C1-3 unsubstituted alkyl group, a C1-3 unsubstituted alkoxy group, a fluorine atom, a chlorine atom, even more preferably a C1-3 unsubstituted alkyl group, a C1-3 unsubstituted alkoxy group.
L1And L2The linking group can be bonded to R constituting the structure of the general formula (1) of Q1～R6L, D, A in a single piece. Two or more linking groups may be linked to one Q to form a cross-linked structure or a network structure.
The structure represented by the general formula (12) or (13) is preferably determined so as not to excessively impair the effects of the present invention.
Specific examples of the structure of the repeating unit include structures represented by the following general formulae (14) to (17).
[ chemical formula 18]
Polymers having repeating units containing these formulas (14) to (17) can be synthesized by: in advanceR for the structure of the formula (1)1～R6L, D, A, a hydroxyl group is introduced, and the following compounds are reacted as a linking group to introduce a polymerizable group, and the polymerizable group is polymerized.
[ chemical formula 19]
The polymer having a structure represented by general formula (1) in a molecule may be a polymer composed only of a repeating unit having a structure represented by general formula (1), or may be a polymer having a repeating unit having a structure other than the above. The number of the repeating units having the structure represented by the general formula (1) contained in the polymer may be one or 2 or more. Examples of the repeating unit not having the structure represented by the general formula (1) include a repeating unit derived from a monomer generally used for copolymerization. For example, a repeating unit derived from a monomer having an ethylenically unsaturated bond such as ethylene or styrene may be mentioned.
[ Synthesis method of Compound represented by the general formula (1) ]
The compound represented by the general formula (1) is a novel compound. The synthesis can be carried out by combining known reactions.
For example, a compound of the general formula (1) in which D is a group represented by the general formula (5) and a is a group represented by the general formula (11) can be synthesized according to the following reaction scheme.
[ chemical formula 20]
With respect to R in the above reaction scheme1～R8For the description of L, R can be described by referring to the corresponding description in the general formula (1)11～R20For the description of (A), the corresponding description in the general formula (5) can be referred to1～A5Can refer to the corresponding in the general formula (11)The description of (1). X1～X3Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. X1And X2Preferably a bromine atom, X3Preferably a chlorine atom.
The above reaction is carried out by applying a known coupling reaction, and the known reaction conditions can be appropriately selected and used. For details of the reaction conditions or steps, reference can be made to the examples described below. The compound represented by the general formula (1) can also be synthesized by combining other known synthesis reactions. For example, in the above reaction scheme, A is introduced after D is introduced, but A may be introduced before D is introduced.
[ organic light-emitting element ]
The compound represented by the general formula (1) of the present invention has excellent light-emitting characteristics, and is therefore useful as a light-emitting material for an organic light-emitting element. The compound represented by the general formula (1) contains a delayed fluorescent material (delayed phosphor) that emits delayed fluorescence. That is, the present application also discloses an invention of a delayed phosphor having a structure represented by general formula (1), an invention using a compound represented by general formula (1) as a delayed phosphor, and an invention of a method for emitting delayed fluorescence using a compound represented by general formula (1). According to the present invention, the necessity of dihedral angle control of donor and acceptor groups for designing molecules emitting delayed fluorescence is greatly reduced.
An organic light-emitting element using a compound that emits delayed fluorescence as a light-emitting material has characteristics in that delayed fluorescence is emitted, the light-emitting efficiency is high, and non-radiative deactivation can be suppressed. The principle of the organic electroluminescence device will be described below by way of example.
In an organic electroluminescent element, carriers are injected from both positive and negative electrodes into a light-emitting material, and the light-emitting material in an excited state is generated to emit light. In general, in the case of a carrier injection type organic electroluminescent element, 25% of generated excitons are excited to an excited singlet state and the remaining 75% are excited to an excited triplet state. Therefore, phosphorescence, which is light emission from an excited triplet state, is utilized, and the energy utilization efficiency is higher. However, since the excited triplet state has a long lifetime, energy deactivation due to saturation of the excited state or interaction with an exciton of the excited triplet state occurs, and generally, the quantum yield of phosphorescence is not high in many cases. On the other hand, the delayed fluorescent material transfers energy to an excited triplet state by intersystem crossing or the like, and then, the delayed fluorescent material reversely crosses to an excited singlet state by triplet-triplet annihilation or absorption of thermal energy, and emits fluorescence. Among organic electroluminescent elements, a thermally activated delayed fluorescent material based on absorption of thermal energy is considered to be particularly useful. In the case where a delayed fluorescence material is used for the organic electroluminescent element, excitons that excite a singlet state emit fluorescence as usual. On the other hand, excitons that excite the triplet state absorb heat emitted from the device and cross-over to the excited singlet state, emitting fluorescence. At this time, since the fluorescence is emitted from the excited singlet state, the fluorescence is emitted at the same wavelength, and the lifetime (emission lifetime) of the generated light is longer than that of the normal fluorescence by the transition from the excited triplet state reverse system to the excited singlet state, and thus the fluorescence is observed as fluorescence delayed from the above. This can be defined as delayed fluorescence. When such a thermally activated reverse intersystem crossing mechanism is used, the ratio of a compound that normally generates only 25% of an excited singlet state can be increased to 25% or more by absorption of thermal energy after carrier injection. When a compound which emits strong fluorescence and delayed fluorescence even at a relatively low temperature of less than 100 ℃ is used, the cross-over from the excited triplet state to the excited singlet state occurs sufficiently by the heat of the device, and delayed fluorescence is emitted, so that the light emission efficiency can be dramatically improved, and the non-radiative deactivation can be suppressed.
The compound represented by the general formula (1) is an excellent light-emitting material capable of emitting delayed fluorescence because the molecule is designed to control the distance between the donor group and the acceptor group within a desired range. The compound represented by the general formula (1) has a structure in which a donor group and an acceptor group are bonded at a specific position of a condensed polycyclic structure, and thus the distance between the donor group and the acceptor group is naturally controlled within a specific range. In particular, in the general formula (1) R7And L each otherBonded to form a cyclic structure or R8And L are bonded to each other to form a cyclic structure, the condensed polycyclic structure becomes a more rigid structure, and thus the distance between the donor group and the acceptor group is substantially fixed. For example, in the case of compounds in which the donor group and the acceptor group of compounds 1 to 5 are bonded to a Triptycene (Triptycene) skeleton, the distance between the donor group and the acceptor group is 4.718 angstroms in an optimized structure calculated based on dft (sensitivity Functional theory).
FIG. 1 is a schematic diagram showing the respective distributions of HOMO and LUMO of Compound 1 calculated by the LC- ω PBE/6-31+ G (d) method. The compound represented by the general formula (1) substantially shows the same HOMO and LUMO distributions as those in fig. 1, and the HOMO and LUMO are roughly classified into a donor group D and an acceptor group a, respectively. The fused polycyclic structure of the bond of the donor group D and the acceptor group A does not substantially affect the HOMO, LUMO. Thus, the condensed polycyclic structure functions to dispose the donor group D and the acceptor group A at an appropriate distance, characterized in that the distance is a distance favorable for delaying fluorescence emission. Thus, the present invention provides for the first time the following concepts: the molecules are designed to control the distance between the donor group and the acceptor group within a range favorable for delayed fluorescence emission, thereby providing excellent delayed fluorescence materials. The distance between the donor group and the acceptor group is preferably 3.00 to 5.50 angstroms, more preferably 4.00 to 5.00 angstroms, and further preferably 4.50 to 4.72 angstroms. For example, the distance between the donor group and the acceptor group may be selected from the range of 4.40 to 4.80 angstroms, or from the range of 4.45 to 4.75 angstroms, or from the range of 4.60 to 4.72 angstroms. Also, the condensed polycyclic structure in which the donor group and the acceptor group are bonded particularly preferably contains a linking moiety that blocks the conjugated system in the shortest linking chain that links the donor group and the acceptor group. In the general formula (1), -C (R)7)(R8) The moiety becomes a linking moiety that blocks the conjugated system. As one mode of the concept of the present invention configured to separate a donor group and an acceptor group by an appropriate distance by a condensed polycyclic structure including such a linking moiety blocking a conjugated system, a compound represented by general formula (1) is provided. According to the concept of the present invention, it is designed to arrange the distance between the donor group and the acceptor groupMolecules within the above preferred range, which are compounds having structures other than general formula (1), can further provide an excellent delayed fluorescent material.
In addition, the "distance between the donor group and the acceptor group" as used herein refers to a straight-line distance between an atom having a linkage of the donor group and an atom having a linkage of the acceptor group. For example, as long as the compound represented by the general formula (1) is a linear distance between an atom which is a constituent atom of the donor group D and has a linking bond for bonding to the condensed polycyclic structure and an atom which is a constituent atom of the acceptor group a and has a linking bond for bonding to the condensed polycyclic structure.
The compound represented by the general formula (1) of the present invention can be formed into a film by a vacuum deposition method or a coating method, and has a relatively high glass transition temperature (Tg), so that it has high thermal stability and is excellent in practical use. Therefore, by using the compound as a material for an organic light-emitting element, an organic film formed of the compound can be efficiently coated with a uniform film thickness without using a large-scale film formation apparatus, and therefore, the production efficiency of the organic light-emitting element can be remarkably improved. In the compound represented by the general formula (1) of the present invention, the molecular structure serving as the basic skeleton is fixed, and Δ E can be suppressed even in an amorphous filmSTThe degree of freedom in design is large. Further, the organic light-emitting element containing the compound can obtain stable light-emitting performance even under a high-temperature environment, and can be effectively used as a display element of a car navigation system, for example. The compound represented by the general formula (1) of the present invention may contain a structure having circular polarization such as triptycene, and is therefore expected to be used as a circular polarizing plate.
By using the compound represented by the general formula (1) of the present invention as a light-emitting material of a light-emitting layer, an excellent organic light-emitting element such as an organic photoluminescent element (organic PL element) or an organic electroluminescent element (organic EL element) can be provided. In this case, the compound represented by the general formula (1) of the present invention may be a compound having a function of assisting light emission of another light-emitting material included in the light-emitting layer as a so-called assist dopant. That is, the compound represented by the general formula (1) of the present invention contained in the light-emitting layer may be a compound having a lowest excited singlet energy level between the lowest excited singlet energy level of the host material contained in the light-emitting layer and the lowest excited singlet energy level of the other light-emitting material contained in the light-emitting layer.
The organic photoluminescent element has a structure in which at least a light-emitting layer is formed on a substrate. The organic electroluminescent element has at least an anode, a cathode, and an organic layer formed between the anode and the cathode. The organic layer may be composed of only the light-emitting layer, including at least the light-emitting layer, or may have 1 or more organic layers other than the light-emitting layer. Examples of such other organic layers include a hole transport layer, a hole injection layer, an electron blocking layer, a hole blocking layer, an electron injection layer, an electron transport layer, and an exciton blocking layer. The hole transport layer may be a hole injection transport layer having a hole injection function, and the electron transport layer may be an electron injection transport layer having an electron injection function. Fig. 2 shows an example of a specific structure of the organic electroluminescent element. In fig. 2, 1 denotes a substrate, 2 denotes an anode, 3 denotes a hole injection layer, 4 denotes a hole transport layer, 5 denotes a light emitting layer, 6 denotes an electron transport layer, and 7 denotes a cathode.
The components and layers of the organic electroluminescent element will be described below. The description of the substrate and the light-emitting layer also corresponds to the substrate and the light-emitting layer of the organic photoluminescent element.
(substrate)
The organic electroluminescent element of the present invention is preferably supported by a substrate. The substrate is not particularly limited as long as it is a substrate conventionally used in organic electroluminescent devices, and for example, a substrate made of glass, transparent plastic, quartz, silicon, or the like can be used.
(Anode)
As the anode of the organic electroluminescent element, an anode using a metal, an alloy, a conductive compound, or a mixture thereof having a large work function (4eV or more) as an electrode material can be preferably used. Specific examples of such electrode materials include metals such as AuCuI, Indium Tin Oxide (ITO), SnO2And conductive transparent materials such as ZnO. Also, IDIXO (In) may be used2O3-ZnO) and the like, and can be used for producing a transparent conductive film. The anode may be formed by forming these electrode materials into a thin film by a method such as vapor deposition or sputtering and forming a pattern of a desired shape by photolithography, or may be formed into a pattern through a mask of a desired shape when the accuracy of the pattern is not high (about 100 μm or more). Alternatively, when a material that can be applied such as an organic conductive compound is used, a wet film formation method such as a printing method or a coating method can be used. When light emission is extracted from the anode, the transmittance is preferably set to be higher than 10%, and the sheet resistance of the anode is preferably several hundred Ω/sq. The film thickness depends on the material, and is usually selected within the range of 10 to 1000nm, preferably 10 to 200 nm.
(cathode)
On the other hand, as the cathode, a metal having a small work function (4eV or less) (referred to as an electron-injecting metal), an alloy, a conductive compound, or a mixture thereof can be used as an electrode material. Specific examples of such electrode materials include sodium, sodium-potassium alloys, magnesium, lithium, magnesium/copper mixtures, magnesium/silver mixtures, magnesium/aluminum mixtures, magnesium/indium mixtures, and aluminum/aluminum oxide (Al)2O3) Mixtures, indium, lithium/aluminum mixtures, rare earth metals, and the like. Among them, from the viewpoint of electron injection property and durability against oxidation and the like, a mixture of an electron-injecting metal and a second metal which is a metal having a larger and more stable work function than the electron-injecting metal is preferable, and examples thereof include a magnesium/silver mixture, a magnesium/aluminum mixture, a magnesium/indium mixture, and aluminum/aluminum oxide (Al)2O3) Mixtures, lithium/aluminum mixtures, aluminum, and the like. The cathode can be produced by forming these electrode materials into a thin film by a method such as vapor deposition or sputtering. The sheet resistance of the cathode is preferably several hundred Ω/sq (ohms per square) or less, and the film thickness is usually selected in the range of 10nm to 5 μm, preferably 50 to 200 nm. In addition, theIt is preferable that either the anode or the cathode of the organic electroluminescent element is transparent or translucent in order to transmit the emitted light, since the emission luminance is improved.
Further, by using the conductive transparent material mentioned in the description of the anode for the cathode, a transparent or translucent cathode can be produced, and by applying the cathode, two elements having transparency, that is, the anode and the cathode, can be produced.
(luminescent layer)
The light-emitting layer is a layer which emits light after excitons are generated by recombination of holes and electrons injected from the anode and the cathode, and a light-emitting material alone may be used for the light-emitting layer. As the light-emitting material, 1 or 2 or more selected from the group of compounds of the present invention represented by general formula (1) can be used. In order to achieve high luminous efficiency in the organic electroluminescent device and the organic photoluminescent device of the present invention, it is important to enclose singlet excitons and triplet excitons generated in the light-emitting material. Therefore, it is preferable to use a host material in addition to the light-emitting material in the light-emitting layer. As the host material, an organic compound having at least one value higher than the excited singlet energy or the excited triplet energy of the light-emitting material of the present invention can be used. As a result, the singlet excitons and the triplet excitons generated in the light-emitting material of the present invention can be encapsulated in the molecules of the light-emitting material of the present invention, and the light-emitting efficiency can be sufficiently exhibited. Of course, since high light emission efficiency can be obtained even if singlet excitons and triplet excitons cannot be sufficiently confined, the present invention can be used without particular limitation as long as the host material can achieve high light emission efficiency. In the organic light-emitting element or the organic electroluminescent element of the present invention, light emission is generated by the light-emitting material of the present invention contained in the light-emitting layer. The luminescence includes both fluorescence and delayed fluorescence. Here, part or part of the light emission may have light emission from the host material.
In the case of using a host material, the compound of the present invention as a light-emitting material is contained in the light-emitting layer in an amount of preferably 0.1% by volume or more, more preferably 1% by volume or more, and preferably 50% by volume or less, more preferably 20% by volume or less, and further preferably 10% by volume or less.
The host material in the light-emitting layer is preferably an organic compound having hole transport ability and electron transport ability, preventing the emission from having a long wavelength, and having a high glass transition temperature.
(injection layer)
The injection layer is a layer provided between an electrode and an organic layer for the purpose of reducing a driving voltage or improving a light emission luminance, and may be a layer including a hole injection layer and an electron injection layer, and may be provided between an anode and a light emitting layer or a hole transport layer, and between a cathode and a light emitting layer or an electron transport layer, respectively. The injection layer can be provided as desired.
(Barrier layer)
The blocking layer is a layer capable of preventing diffusion of charges (electrons or holes) and/or excitons present in the light-emitting layer out of the light-emitting layer. The electron blocking layer can be disposed between the light-emitting layer and the hole transport layer, and prevents electrons from passing through the light-emitting layer toward the hole transport layer. Similarly, the hole blocking layer can be disposed between the light-emitting layer and the electron transport layer, and prevents holes from passing through the light-emitting layer toward the electron transport layer. The blocking layer can also be used in order to prevent excitons from diffusing to the outside of the light-emitting layer. That is, the electron blocking layer and the hole blocking layer can also function as an exciton blocking layer. The electron blocking layer or the exciton blocking layer described in this specification is used in a sense of including a layer having functions of the electron blocking layer and the exciton blocking layer as one layer. The barrier layer can be provided as desired.
(hole blocking layer)
The hole blocking layer has a function of an electron transport layer in a broad sense. The hole blocking layer has a function of transporting electrons and preventing holes from reaching the electron transporting layer, whereby the probability of recombination of electrons and holes in the light emitting layer can be increased. As the material of the hole blocking layer, a material of an electron transport layer described later can be used as necessary.
(Electron blocking layer)
The electron blocking layer has a function of transporting holes in a broad sense. The electron blocking layer has a function of transporting holes and preventing electrons from reaching the hole transporting layer, whereby the probability of recombination of electrons and holes in the light emitting layer can be increased.
(exciton blocking layer)
The exciton-blocking layer is a layer for blocking diffusion of excitons generated by recombination of holes and electrons in the light-emitting layer to the charge transport layer, and the excitons can be efficiently confined in the light-emitting layer by insertion of the layer, and the light-emitting efficiency of the device can be improved. The exciton blocking layer may be inserted into either the anode side or the cathode side adjacent to the light-emitting layer, or may be inserted into both sides. That is, when the exciton-blocking layer is provided on the anode side, the layer can be inserted between the hole-transporting layer and the light-emitting layer so as to be adjacent to the light-emitting layer, and when the exciton-blocking layer is inserted on the cathode side, the layer can be inserted between the light-emitting layer and the cathode so as to be adjacent to the light-emitting layer. Further, a hole injection layer, an electron blocking layer, or the like may be provided between the anode and the exciton blocking layer adjacent to the anode side of the light-emitting layer, and an electron injection layer, an electron transport layer, a hole blocking layer, or the like may be provided between the cathode and the exciton blocking layer adjacent to the cathode side of the light-emitting layer. In the case where the blocking layer is provided, at least one of excited singlet energy and excited triplet energy of a material used as the blocking layer is preferably higher than excited singlet energy and excited triplet energy of the light-emitting material.
(hole transport layer)
The hole transport layer is made of a hole transport material having a function of transporting holes, and the hole transport layer can be provided in a single layer or a plurality of layers.
The hole transport material may be either an organic material or an inorganic material, having hole injection or transport properties or electron blocking properties. Examples of the known hole-transporting material that can be used include triazole derivatives, oxadiazole derivatives, imidazole derivatives, carbazole derivatives, indolocarbazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, and aniline copolymers, and further include conductive polymer oligomers, particularly thiophene oligomers, and the like.
(Electron transport layer)
The electron transport layer is made of a material having a function of transporting electrons, and the electron transport layer can be provided in a single layer or a plurality of layers.
The electron transport material (which may also serve as a hole blocking material) may have a function of transporting electrons injected from the cathode to the light-emitting layer. Examples of the electron transport layer that can be used include nitro-substituted fluorene derivatives, diphenylquinone derivatives, Thiopyran dioxide (thiopyrane dioxide) derivatives, carbodiimides, fluorenylidene methane derivatives, anthraquinone dimethane (anthraquinone dimethane), anthrone derivatives, and oxadiazole derivatives. Further, of the oxadiazole derivatives, a thiadiazole derivative obtained by substituting an oxygen atom of an oxadiazole ring with a sulfur atom, and a quinoxaline derivative having a quinoxaline ring known as an electron-withdrawing group can also be used as the electron-transporting material. Further, a polymer material in which these materials are introduced into a polymer chain or a main chain of a polymer can be used.
In the production of an organic electroluminescent element, the compound represented by the general formula (1) may be used not only for the light-emitting layer but also for layers other than the light-emitting layer. In this case, the compound represented by the general formula (1) used in the light-emitting layer and the compound represented by the general formula (1) used in a layer other than the light-emitting layer may be the same or different. For example, the compound represented by the general formula (1) may be used for the injection layer, the blocking layer, the hole blocking layer, the electron blocking layer, the exciton blocking layer, the hole transport layer, the electron transport layer, and the like. The method for forming these layers is not particularly limited, and the layers may be formed by either a dry process or a wet process.
Hereinafter, preferred materials that can be used for the organic electroluminescent element are specifically exemplified. The materials that can be used in the present invention are not to be construed as being limited by the following exemplified compounds. Further, even a compound exemplified as a material having a specific function can be used as a material having another function. In the structural formula of the following exemplary compound, n represents an integer of 3 to 5.
First, preferred compounds that can also be used as host materials for the light-emitting layer are listed.
[ chemical formula 21]
[ chemical formula 22]
[ chemical formula 23]
[ chemical formula 24]
[ chemical formula 25]
Next, preferred examples of compounds that can be used as the hole injection material are given.
[ chemical formula 26]
Next, preferred examples of compounds that can be used as the hole transport material are given.
[ chemical formula 27]
[ chemical formula 28-1]
[ chemical formula 28-2]
[ chemical formula 29]
[ chemical formula 30]
[ chemical formula 31]
[ chemical formula 32]
Next, preferred examples of compounds that can be used as an electron blocking material are given.
[ chemical formula 33]
Next, preferred examples of compounds that can be used as the hole blocking material are given.
[ chemical formula 34]
Next, preferred examples of compounds that can be used as an electron transporting material are given.
[ chemical formula 35]
[ chemical formula 36]
[ chemical formula 37]
Next, preferred examples of compounds that can be used as an electron injecting material are given.
[ chemical formula 38]
Further, examples of compounds preferable as materials that can be added are given. For example, it is conceivable to add the stabilizer as a stabilizing material.
[ chemical formula 39]
The organic electroluminescent element produced by the above method emits light by applying an electric field between the anode and the cathode of the obtained element. In this case, if the light is emitted based on the excited singlet energy, the light having a wavelength corresponding to the energy level thereof is confirmed to be fluorescence emission and delayed fluorescence emission. When the light is emitted by the excited triplet energy, the wavelength corresponding to the energy level is considered to be phosphorescence. The fluorescence lifetime of normal fluorescence is shorter than delayed fluorescence emission, and therefore the emission lifetime can be distinguished from delayed fluorescence. Here, in the organic light-emitting element of the present invention, the delayed fluorescence component in the emitted light is preferably 50% or more, more preferably 60% or more, and still more preferably 70% or more.
On the other hand, regarding phosphorescence, in a general organic compound such as the compound of the present invention, excited triplet energy is unstable and is converted into heat, etc., and thus the lifetime is short and the phosphorescence is immediately deactivated, and therefore, almost no phosphorescence can be observed at room temperature. In order to measure the excited triplet energy of a general organic compound, it is possible to measure by observing light emission under extremely low temperature conditions.
The organic electroluminescent element of the present invention is applicable to any of individual elements, elements having an array-like structure, and an X-Y matrix-like structure in which an anode and a cathode are arranged. According to the present invention, an organic light-emitting element having greatly improved luminous efficiency can be obtained by including a compound represented by the general formula (1) in a light-emitting layer. The organic light-emitting element such as the organic electroluminescent element of the present invention can be further applied to various applications. For example, an organic electroluminescent display device can be manufactured using the organic electroluminescent element of the present invention, and in detail, reference can be made to an "organic EL display" (Ohmsha, Ltd.) commonly owned by wainshi, andkyush, and cuntian english. In addition, the organic electroluminescent element of the present invention can be applied to organic electroluminescent lighting or backlight which is in great demand.
Examples
The features of the present invention are described below by way of synthesis examples and examplesOne step is specifically explained. The materials, processing contents, processing steps, and the like described below can be modified as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited to the specific examples shown below. For the evaluation of the luminescence properties, a phosphorescence spectrophotometer (HORIBA, manufactured by Ltd.: FluoroMax Plus), a compact fluorescence lifetime measuring apparatus (manufactured by Hamamatsu Photonics K.K.: Quantaurus-Tau C11367-01), a nitrogen cryostat (manufactured by Oxford Instruments: Optis tatDN2), an absolute PL quantum yield measuring apparatus (manufactured by Hamamatsu Photonics K.K.: C9920-02), an external quantum efficiency measuring apparatus (manufactured by Hamamatsu Photonics K.K.: C9920-12) and a source table (manufactured by Keithlshi Photonics K.K.: C9920-02) were used, and for the measurement of CIE color coordinates, a differential thermal scanning apparatus (manufactured by Hamamatsu Photonics K.K.K.: C9920-02) and an external quantum efficiency measuring apparatus (manufactured by Hamamatsu Photonics K.K.: DSC1) were used. About1HNMR, determined using JEOL JNM ECA 600. Chemical shifts are expressed in ppm and the residual solution in solvent (CHCl) is used for the determination37.26ppm) as internal standard. In the column chromatography, Wako sil C-300 was used as silica gel.
(Synthesis example 1) Synthesis of Compound 1
First, compound S-1 as the 1 st intermediate was synthesized in the following manner.
[ chemical formula 40]
1, 8-dibromoanthracene (10g, 29mmol), Isoamyl nitrite (Isoamyl nitrate) (5.75g, 50mmol) were dissolved in 75mL of 1, 2-dimethoxyethane and charged into a 500mL three-necked flask equipped with a reflux tube and a dropping funnel. Ananthranilic acid (8.5g, 60mmol) dissolved in 40mL of 1, 2-dimethoxyethane was added dropwise over 40 minutes while heating and refluxing the reaction mixture. The reaction mixture was cooled to room temperature, and isoamyl nitrite (5.75g, 50mmol) was added thereto, followed by reflux with heating again and dropwise addition of anthranilic acid (8.5g, 60mmol) dissolved in 40mL of 1, 2-dimethoxyethane over 30 minutes. The reaction solution was naturally cooled to room temperature, and 30mL of methanol was added, followed by 250mL of a 10% aqueous solution of sodium hydroxide. The reaction solution was cooled to 10 ℃ and filtered, and then washed with a methanol/water (4/1) solution in which the residue was cooled. Into a 300mL round bottom flask equipped with a reflux tube, the residue, 5g of maleic anhydride and 50mL of triethylene glycol dimethyl ether were charged and heated at 180 ℃ for 15 minutes. The reaction solution was naturally cooled to room temperature, and 200mL of a 10% aqueous solution of sodium hydroxide was added. After the reaction solution was cooled to 10 ℃ and filtered, the residue was washed with a methanol/water (4/1) solution having cooled the residue, whereby 1, 8-dibromotriptycene (compound S-1) was obtained in a yield of 9.8g (24mmol) and a yield of 83%.
1HNMR(600MHz,CDCl3)：7.53-7.51(m,1H),7.41-7.40(m,1H),7.31(d,J＝6.0Hz,2H),7.21(d,J＝6.0Hz,2H),7.07-7.05(m,2H),6.87(t,J＝9.0Hz,2H),6.51(s,1H),5.43(s,1H)
Next, compound S-2 as the 2 nd intermediate was synthesized in the following manner.
[ chemical formula 41]
Into a 100mL eggplant-shaped flask with a Screw cap (Screw cap), 9-dimethyl-9, 10-dihydroacridine (1.26g, 6.03mmol), a compound S-1(6.18g, 15.1mmol), tris (dibenzylideneacetone) dipalladium (0) -chloroform adduct (186mg, 0.18mmol), XPhos (2-dicyclohexylphosphino-2 ', 4 ', 6 ' -triisopropylbiphenyl) (172mg, 0.36mmol), and sodium tert-butoxide (1.15g, 12.0mmol) were charged, 60mL of toluene was added, and the mixture was stirred overnight at 120 ℃ under an argon atmosphere. The reaction solution was cooled to room temperature, 20mL of water was added, and extracted 3 times with ethyl acetate (100 mL). The organic layer was dried over sodium sulfate and then concentrated, and the residue was purified by silica gel column chromatography (developing solvent: hexane/dichloromethane ═ 4/1), whereby compound S-2 was obtained in a yield of 2.37g and 73%.
1HNMR(600MHz,CDCl3)：7.56-7.52(m,2H),7.49(d,J＝6.0Hz,1H),7.41(d,J＝6.0Hz,1H),7.34(d,J＝6.0Hz,1H),7.24(t,J＝6.0Hz,1H),7.05(d,J＝6.0Hz,1H),7.02(t,J＝6.0Hz,1H),6.98-6.90(m,5H),6.85-6.76(m,3H),5.87(d,J＝12.0Hz,1H),5.76(d,J＝12.0Hz,1H),5.72(s,1H),5.55(s,1H),1.93(s,3H),1.70(s,3H)
Next, compound S-3 as the 3 rd intermediate was synthesized in the following manner.
[ chemical formula 42]
A50 mL two-necked flask was charged with compound S-2(1.77g, 3.27mmol) and dissolved in 25mL of dry tetrahydrofuran. The reaction mixture was cooled to-78 ℃ under an argon atmosphere, and 3.0mL of an n-butyllithium hexane solution (1.6mol/L) was slowly added dropwise. After stirring at-78 ℃ for 2 hours, isopropanol pinacol borate (0.78mL, 3.87mmol) was added and the mixture was slowly returned to room temperature while stirring overnight. The reaction solution was added to 1M aqueous hydrochloric acid solution, and extracted 3 times with ethyl acetate (50 mL). The organic layer was washed with water and saturated brine, dried over sodium sulfate, concentrated, and the residue was purified by silica gel column chromatography (developing solvent: hexane/dichloromethane ═ 7/3), whereby compound S-3 was obtained in a yield of 0.864g and 45%.
1HNMR(600MHz,CDCl3)：7.51-7.49(m,3H),7.43(d,J＝6.0Hz,2H),7.35(d,J＝6.0Hz,1H),7.18-7.14(m,2H),7.04-6.96(m,4H),6.91(t,J＝6.0Hz,1H),6.87-6.84(m,2H),6.72(t,J＝6.0Hz,1H),6.31(s,1H),6.04(d,J＝6.0Hz,1H),5.67(d,J＝6.0Hz,1H),5.57(s,1H),1.95(s,3H),1.43(s,3H),0.94(s,6H),0.81(s,6H)
Next, the target compound 1 was synthesized in the following manner.
[ chemical formula 43]
Into a 100mL eggplant-shaped flask with a screw cap were charged the compound S-3(0.85g, 1.45mmol), 2-chloro-4, 6-diphenyl-1, 3, 5-triazine (0.58g, 2.17mmol), tetrakis (triphenylphosphine) palladium (0) (168mg, 0.15mmol), and 60mL of toluene and 6.0mL of an aqueous solution of potassium carbonate (2.0M) were added. The mixture was degassed by freezing 3 times, and heated and stirred at 120 ℃ for 24 hours under an argon atmosphere. The reaction solution was cooled to room temperature, 40mL of water was added, and extracted 3 times with ethyl acetate (50 mL). The organic layer was dried over sodium sulfate and then concentrated, and the residue was purified by silica gel column chromatography (developing solvent: hexane/dichloromethane ═ 4/1), whereby compound 1 was obtained in a yield of 0.679g and 68%. The glass transition temperature (Tg) of Compound 1 was measured and found to be 135 ℃ and higher than the glass transition temperature (91 ℃) of DMAC-TRZ used in comparative example 1, and it was confirmed that the thermal stability was high.
1HNMR(600MHz,CDCl3)：8.47(d,J＝6.0Hz,4H),8.25(d,J＝6.0Hz,1H),7.66(d,J＝6.0Hz,1H),7.58-7.56(m,3H),7.51(d,J＝6.0Hz,1H),7.45(t,J＝9.0Hz,4H),7.25-7.20(m,4H),7.14(d,J＝6.0Hz,1H),7.09(t,J＝6.0Hz,1H),7.03(t,J＝6.0Hz,1H),6.96(t,J＝6.0Hz,1H),6.90-6.83(m,3H),6.31(t,J＝9.0Hz,1H),6.13(t,J＝9.0Hz,1H),5.81(d,J＝6.0Hz,1H),5.70(s,1H),5.60(d,J＝6.0Hz,1H),1.23(s,3H),1.11(s,3H)
(Synthesis examples 2 to 6) Synthesis of Compounds 2 to 6
[ chemical formula 44]
Example 1 preparation and evaluation of toluene solution of Compound 1
Compound 1 was dissolved in toluene to prepare 10-5M in toluene.
Ultraviolet-visible (UV-Vi s) absorption spectra of the prepared toluene solution of the compound 1 are shown in fig. 3(a), 3(b), and emission spectra based on excitation light of 320nm are shown in fig. 4.
FIG. 3(a) is an absorption spectrum in the range of 300 to 600nm, and FIG. 3(b) is an enlarged view of the range of 350 to 500nm in the absorption spectrum shown in FIG. 3 (a). As shown in FIGS. 3(a) and 3(b), from the toluene solution of Compound 1, strong absorption having a shoulder at around 300nm and extremely weak absorption in a broad band at around 350 to 400nm were observed. And the absorption coefficient in the weak absorption is about 250cm-1M-1. The extremely weak absorption at 350 to 400nm means high transmittance of visible light (high color transparency). Therefore, the compound represented by the general formula (1) is very useful as a light-emitting material.
As shown in fig. 4, blue-green emission having a very large emission near 485nm was observed from the toluene solution of compound 1. The PL quantum yield based on 365nm excitation light was measured before and after Ar bubbling of this toluene solution of compound 1, and showed a very weak PL quantum yield of 2% ± 1% before Ar bubbling, whereas a greatly improved PL quantum yield of 84% ± 1% after Ar bubbling. The PL quantum yield before Ar bubbling was lower than after Ar bubbling, which is believed to be because the excited triplet state was quenched by dissolved oxygen in the toluene solution. Thus, it is suggested that the luminescence of compound 1 contains delayed fluorescence associated with cross-over from excited triplet-inverted to excited singlet state. Further, since the luminescence quantum yield significantly changes depending on the presence or absence of dissolved oxygen in a solution, the compound represented by the general formula (1) is also very useful as a material for an oxygen sensor.
Example 2 production and evaluation of organic photoluminescent element Using Compound 1
A thin film of compound 1 was formed on a quartz glass substrate by a vacuum deposition method, and used as an organic photoluminescent element. Here, the degree of vacuum at the time of vapor deposition was set to 1X 10-4Pa, and the thickness of the film was 38 nm.
Fig. 5 shows a transient decay curve of the luminescence measured at 300K for the prepared thin film of compound 1. The transient decay curve of luminescence in fig. 5 was measured with the excitation wavelength of 365nm and the detection wavelength of luminescence of 504 nm.
As a result of measuring the emission spectrum of the compound 1 thin film with excitation light of 320nm, a light emission peak having a maximum emission near 504nm was observed. And, the PL quantum yield at an excitation wavelength of 320nm was 71% under a nitrogen stream.
Then, compound 1 and CzSi were co-evaporated on quartz glass under the same conditions as described above to obtain a thin film (25 vol% for compound 1). The film had a photoluminescence quantum yield of 82%, a maximum luminescence wavelength of 483nm, CIE (x, y) (0.18,0.31), and τ d of 5.0 μ s.
Then, compound 1 and mCPCN were co-evaporated on quartz glass under the same conditions as described above to obtain a thin film (compound 1: 22 vol%). The film had a photoluminescence quantum yield of 64%, a maximum luminescence wavelength of 489nm, CIE (x, y) of (0.20,0.40), and τ d of 3.9 μ s. From the above results, when comparing mCPCN with CzSi, CzSi was found to be a more preferable host material.
Then, compound 1, CzSi, and TBPe were co-evaporated on quartz glass under the same conditions as described above to obtain a thin film (compound 1: 26 vol%, TBPe: 4 vol%). The film had a photoluminescence quantum yield of 87%, a maximum luminescence wavelength of 461nm, CIE (x, y) of (0.14,0.23), and τ d of 0.36 μ s. The results are shown below: the compounds of the present invention are useful as auxiliary dopants and efficiently produce TAF (TADF assisted fluorescence). Further, it also shows that extremely fast delayed fluorescence and desired blue light emission can be realized.
Example 3 evaluation of Compounds 2 to 6
[ Table 1]
| Compound numbering | CIE(x,y) |
| Compound 1 | (0.19,0.36) |
| Compound 2 | (0.30,0.56) |
| Compound 3 | (0.56,0.44) |
| Compound 4 | (0.16,0.11) |
| Compound 5 | (0.41,0.55) |
| Compound 6 | (0.49,0.50) |
Example 4 production and evaluation of organic electroluminescent element Using Compound 1
By vacuum evaporation method, toDegree of vacuum of 2X 10-4Pa or less, each thin film was laminated on a glass substrate on which an anode made of indium/tin oxide (ITO) having a film thickness of 50nm was formed. First, TAPC with a thickness of 60nm was formed on ITO, and mAP with a thickness of 10nm was formed thereon. Then, the compound 1 and mCBP were co-evaporated from different evaporation sources to form a layer having a thickness of 30nm, which was used as a light-emitting layer. At this time, the concentration of compound 1 was set to 25 vol%. Next, on the light emitting layer, PPF was formed to a thickness of 10nm, and on top thereof, BmPyPhB was formed to a thickness of 35 nm. Subsequently, Liq was formed to a thickness of 1nm, and Al was deposited thereon to a thickness of 80nm, thereby forming a cathode.
Through the above steps, an organic electroluminescent element (element 1) having a layer structure of ITO (50nm)/TAPC (60 nm)/mapp (10nm)/25 vol% of compound 1, mCBP (30nm)/PPF (10nm)/BmPyPhB (35nm)/Liq (1nm)/Al (80nm) (wherein "/" represents a boundary of a layer, and the thickness in parentheses represents a numerical film) was obtained.
The current density-voltage-luminance characteristics of the fabricated element 1 are shown in FIG. 6 and will be 10000cd/m2And 20000cd/m2The external quantum efficiencies measured below are shown in table 2.
As for the element 1, as a result of measuring the external quantum efficiency-luminance characteristic, the external quantum efficiency showed 19.2% at the maximum at 1000cd/m2The extremely high luminous efficiency of 18.1% was also maintained. And, the element 1 is at 1000cd/m2Lower luminescence maximum wavelength λMAXThe CIE color coordinate (x, y) of the emission is (0.20,0.44) at 496 nm.
Comparative example 1 production and evaluation of organic electroluminescent element Using DMAC-TRZ
An organic electroluminescent element (comparative element 1) was produced in the same manner as in example 4, except that DMAC-TRZ was used instead of compound 1. The layer structure of the comparative element 1 thus produced was ITO (50nm)/TAPC (60nm)/mAP (10nm)/25 vol% DMAC-TRZ, mCBP (30nm)/PPF (10nm)/BmPyPhB (35nm)/Liq (1nm)/Al (80 nm). DMAC-TRZ is a molecule having a donor group and an acceptor group in common with compound 1.
The current density of the manufactured comparative element 1 was measuredThe results of the degree-voltage-luminance characteristics are shown in fig. 6. 10000cd/m2And 20000cd/m2The external quantum efficiencies below are shown in table 2. Further, the CIE color coordinates (x, y) of the light emission of the comparative element 1 were (0.21,0.48), and the light emission color similar to that of the element 1 was exhibited.
[ Table 2]
10000cd/m, as shown in Table 12And 20000cd/m2The lower external quantum efficiency obtained a higher value in element 1 than in comparative element 1. E.g. at 10000cd/m2In the element 1, the external quantum efficiency can be increased by 10% or more compared to the comparative element 1. Therefore, it was confirmed that the light emission efficiency in the high current density region was greatly improved by using the bonding position of the core skeleton represented by the general formula (1) and the donor group and the acceptor group thereof.
Example 5 production and evaluation of another organic electroluminescent element Using Compound 1
In the production process of example 4, the light-emitting layer was changed to 27 vol% of compound 1 and CzSi, and an organic electroluminescent element (element 2) having a layer structure of ITO (50nm)/TAPC (60nm)/mAP (10nm)/27 vol% of compound 1, CzSi (30nm)/PPF (10nm)/BmPyPhB (35nm)/Liq (1nm)/Al (80nm) was obtained.
In the production process of example 4, the light-emitting layer was changed to 1 vol% of TBPe, 24 vol% of compound 1, and 75 vol% of CzSi, and an organic electroluminescent element (element 3) having a layer structure of ITO (50nm)/TAPC (60nm)/mAP (10nm)/1 vol% of TBPe, 24 vol% of compound 1, 75 vol% CzSi (30nm)/PPF (10nm)/BmPyPhB (35nm)/Liq (1nm)/Al (80nm) was obtained.
Evaluation was performed in the same manner as in example 4, and CIE (x, y) was also determined. The results are shown in the following table. The results of the table show: by using the compound of the present invention, taf (tadf-associated fluorescence) can be realized with high luminance with good efficiency in a desired blue emission color.
[ Table 3]
[ chemical formula 45]
Industrial applicability
The compound of the present invention is a light-emitting material useful for exhibiting higher light-emitting efficiency than conventional delayed phosphors and having high thermal stability. Therefore, the compound of the present invention can be practically used as a light-emitting material for an organic light-emitting element such as an organic electroluminescent element, and an organic light-emitting element having high light-emitting efficiency and good thermal stability can be realized. Therefore, the present invention has high industrial applicability.
Description of the symbols
1-substrate, 2-anode, 3-hole injection layer, 4-hole transport layer, 5-luminescent layer, 6-electron transport layer, 7-cathode.
Claims (25)
1. A compound, wherein,
the local excited triplet level E (3LE), the charge transfer type lowest excited singlet level E (1CT), and the charge transfer type lowest excited triplet level E (3CT) are within an energy width of 0.3eV in each individual compound.
2. The compound of claim 1, wherein,
the reverse intersystem crossing velocity constant k between excited singlet and triplet statesRISCIs 1 × 106s-1The above.
3. The compound of claim 2, wherein,
the reverse intersystem crossing velocity constant k between excited singlet and triplet statesRISCIs 1 × 107s-1The above.
4. The compound according to any one of claims 1 to 3, which has a structure in which a donor group and an acceptor group are bonded to a ring skeleton, respectively.
5. The compound of claim 4, wherein,
the distance between the atom constituting the donor group and bonded to the ring skeleton and the atom constituting the acceptor group and bonded to the ring skeleton is structurally fixed.
6. The compound according to any one of claims 1 to 5, consisting of only carbon atoms, hydrogen atoms and nitrogen atoms.
7. A compound represented by the following general formula (1) wherein,
[ chemical formula 1]
General formula (1)
In the general formula (1), R1～R6Each independently represents a hydrogen atom or a substituent, R7And R8Each independently represents a hydrogen atom or an alkyl group or R7And R8Are bonded to each other to form a cyclic structure, L represents a single bond or a linking group, or R7And L are bonded to each other to form a cyclic structure, or R8And L are bonded to each other to form a cyclic structure, D represents a donor group, and A represents an acceptor group.
8. The compound of claim 7, wherein,
both D and A in the general formula (1) have an aromatic ring.
9. The compound of claim 8, wherein,
d and A in the general formula (1) are both aromatic rings and are bonded to the ring skeleton of the general formula (1).
10. The compound according to any one of claims 7 to 9, wherein,
r in the general formula (1)7Bonded to L to form a ring structure.
11. The compound according to any one of claims 7 to 10, wherein,
l in the general formula (1) is a single bond, -O-, -S-, -N (R)81)-、-C(R82)(R83) -or-Si (R)84)(R85) -, said R81～R85Each independently represents a hydrogen atom or a substituent or with R7Or R8Bonded to form a ring structure.
12. The compound of claim 11, wherein,
l in the general formula (1) is-N (R)81)-、-C(R82)(R83) -or-Si (R)84)(R85) -, said R81～R85Any of (1) and R7Or R8The cyclic structure formed by bonding includes a linking group having a linking chain length of 1 to 3 atoms.
13. The compound of claim 12, wherein R81～R85And R7Or R8The cyclic structure formed by bonding comprises a 1, 2-phenylene structure.
14. A light-emitting material comprising the compound of any one of claims 1 to 13.
15. A delayed phosphor comprising the compound of any one of claims 1 to 13.
16. An organic light-emitting element comprising the compound according to any one of claims 1 to 13.
17. The organic light-emitting element according to claim 16, which is an organic electroluminescent element.
18. The organic light-emitting element according to claim 16 or 17, which comprises the compound in a light-emitting layer.
19. The organic light-emitting element according to claim 18,
the light emitting layer includes a host material.
20. The organic light-emitting element according to claim 19,
the local excited triplet level E (3LE), the charge transport lowest excited singlet level E (1CT), and the charge transport lowest excited triplet level E (3CT) of the light-emitting layer including the host material and the compound are all within the range of the energy width of 0.3 eV.
21. An oxygen sensor comprising the compound of any one of claims 1 to 13.
22. Use of a compound as a luminescent material, wherein,
the local excited triplet level E (3LE), the charge-transporting lowest excited singlet level E (1C T), and the charge-transporting lowest excited triplet level E (3CT) of the compound are all within the energy width range of 0.3 eV.
23. Use of a composition as a luminescent material, wherein,
the composition contains a compound in which a local excited triplet level E (3LE), a charge-moving lowest excited singlet level E (1C T), and a charge-moving lowest excited triplet level E (3CT) are all within a range of an energy width of 0.3eV, and does not contain a solvent and a host material.
24. A method of designing a molecule having a donor group and an acceptor group,
the distance between the donor group and the acceptor group is determined so that the local excited triplet level E (3LE), the charge-transporting lowest excited singlet level E (1CT) and the charge-transporting lowest excited triplet level E (3CT) are all within the energy width of 0.3eV, and the donor group and the acceptor group are structurally fixed so as not to vary the distance.
25. A program for performing the method of claim 24 to design a molecule.
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| JP2018-179327 | 2018-09-25 | ||
| JP2018179327 | 2018-09-25 | ||
| PCT/JP2019/037565 WO2020067143A1 (en) | 2018-09-25 | 2019-09-25 | Compound, luminescent material, delayed fluorescent substance, organic luminescent element, oxygen sensor, and method and program for designing molecule |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023052275A1 (en) * | 2021-09-28 | 2023-04-06 | Merck Patent Gmbh | Materials for electronic devices |
| CN116102560A (en) * | 2023-04-07 | 2023-05-12 | 季华实验室 | Triptycene compound, preparation method thereof and light-emitting device |
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| CN111848424B (en) * | 2020-08-05 | 2024-06-18 | 厦门稀土材料研究所 | Thermal activation delayed fluorescent material containing triptycene group and preparation method and application thereof |
| US20240023437A1 (en) * | 2020-11-17 | 2024-01-18 | Kyulux, Inc. | Organic electroluminescence element, and design method and program for light emitting composition |
| JP2022142304A (en) * | 2021-03-16 | 2022-09-30 | 株式会社Kyulux | Composition, use of the composition as light-emitting composition, film, use of the film as light-emitting film, organic electroluminescent element, design method for composition, and program for implementing the design method |
| CN118056486A (en) * | 2021-09-28 | 2024-05-17 | 默克专利有限公司 | Material for electronic devices |
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| US20150137084A1 (en) * | 2013-11-15 | 2015-05-21 | National Tsing Hua University | Triptycene derivatives having symmetric or asymmetric substituents and organic light emitting diode using the same |
| JP2016036025A (en) * | 2014-07-31 | 2016-03-17 | コニカミノルタ株式会社 | ORGANIC ELECTROLUMINESCENT DEVICE AND π CONJUGATED COMPOUND |
| US20180159050A1 (en) * | 2016-12-07 | 2018-06-07 | Samsung Display Co., Ltd. | Condensed cyclic compound and organic light-emitting device including the same |
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| WO2016201052A1 (en) | 2015-06-12 | 2016-12-15 | Global Blood Therapeutics, Inc. | Bridged bicyclic kallikrein inhibitors |
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|---|---|---|---|---|
| US20150137084A1 (en) * | 2013-11-15 | 2015-05-21 | National Tsing Hua University | Triptycene derivatives having symmetric or asymmetric substituents and organic light emitting diode using the same |
| JP2016036025A (en) * | 2014-07-31 | 2016-03-17 | コニカミノルタ株式会社 | ORGANIC ELECTROLUMINESCENT DEVICE AND π CONJUGATED COMPOUND |
| US20180159050A1 (en) * | 2016-12-07 | 2018-06-07 | Samsung Display Co., Ltd. | Condensed cyclic compound and organic light-emitting device including the same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2023052275A1 (en) * | 2021-09-28 | 2023-04-06 | Merck Patent Gmbh | Materials for electronic devices |
| CN116102560A (en) * | 2023-04-07 | 2023-05-12 | 季华实验室 | Triptycene compound, preparation method thereof and light-emitting device |
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| WO2020067143A1 (en) | 2020-04-02 |
| JPWO2020067143A1 (en) | 2021-09-02 |
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