Patent Application
20230345816
The present invention relates to a compound, an organic electroluminescence device, and an electronic device.
Organic electroluminescence devices (hereinafter sometimes referred to as “organic EL devices”) are applied to full-color displays of mobile phones, television sets, and the like. Upon the application of a voltage to an organic EL device, holes are injected into an emitting layer from an anode, and electrons are injected into the emitting layer from a cathode. The holes and electrons injected into the emitting layer recombine and form excitons. According to the statistical law of electron spins, singlet excitons are generated at a rate of 25%, and triplet excitons are generated at a rate of 75%.
To improve the performance of organic EL devices, various studies have been made on compounds used for the organic EL devices (see Patent Literature 1 to Patent Literature 6, for example). The performance of organic EL devices includes luminance, emission wavelength, chromaticity, luminous efficiency, drive voltage, and life, for example.
An object of the invention is to provide a compound that can improve luminous efficiency, an organic EL device produced using the compound, and an electronic device including the organic EL device.
Another object of the invention is to provide an organic electroluminescence device with improved performance. Still another object of the invention is to provide an organic electroluminescence device with improved luminous efficiency and an electronic device including the organic electroluminescence device.
An aspect of the invention provides a compound represented by the following formula (12X).
[Formula 1]
Py1-L1-L2-Py2 (12X)
In the formula (12X):
A substituent F for “substituted or unsubstituted” in the substituent E is each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9′-spirobifluorenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, or a substituted or unsubstituted 9,9-diphenylfluorenyl group.
In the formulae (13-1) to (13-6), R11 to R15 and R11A to R15A each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a group represented by —Si(Rx)(Ry)(Rz), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms;
In the formula (10-1):
In the formulae (20-1) and (30-1):
In a compound represented by the formula (10-1), a combination of R11 and R13 and a combination of R21 and R23 are different combinations, or a combination of R12 and R14 and a combination of R22 and R24 are different combinations.
In a compound represented by the formula (20-1), R31 is different from R41, R32 is different from R42, R33 is different from R43, or R34 is different from R44.
In a compound represented by the formula (30-1), R51 is different from R61, R52 is different from R62, R53 is different from R63, or R54 is different from R64.
In the formula (4):
In the formulae (10-1), (20-1), and (30-1) and the formula (4), a substituent for “substituted or unsubstituted” in R11 to R14, R21 to R24, R31 to R34, R41 to R44, R51 to R54, R61 to R64, and R311 to R319 is each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9′-spirobifluorenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, or a substituted or unsubstituted 9,9-diphenylfluorenyl group.
An aspect of the invention provides a compound represented by the following formula (120).
In the formula (120):
In the formulae (11) to (13) and (11A) to (13A):
An aspect of the invention provides a compound represented by the following formula (1), (2), or (3).
In the formulae (1) to (3):
In the formula (1):
In the formulae (2) to (3):
In a compound represented by the formula (1), a combination of R11 and R13 and a combination of R21 and R23 are different combinations, or a combination of R12 and R14 and a combination of R22 and R24 are different combinations.
In a compound represented by the formula (2), a combination of R31 and R41 is different from at least one combination of a combination of R32 and R42, a combination of R33 and R43, or a combination of R34 and R44.
In a compound represented by the formula (3), a combination of R51 and R61 is different from at least one combination of a combination of R52 and R62, a combination of R53 and R63, or a combination of R54 and R64.
In the formula (4):
In the formulae (1) to (3), a substituent for “substituted or unsubstituted” in R11 to R14, R21 to R24, R31 to R34, R41 to R44, R51 to R54, R61 to R64, R111 to R119, R211 to R219, and R311 to R319 is each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9′-spirobifluorenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, or a substituted or unsubstituted 9,9-diphenylfluorenyl group.
Another aspect of the invention provides an organic electroluminescence device including an anode, a cathode, an emitting layer between the anode and the cathode, in which the emitting layer contains the compound according to the above aspect of the invention as a host material.
Still another aspect of the invention provides an organic electroluminescence device including an anode, a cathode, a first emitting layer between the anode and the cathode, and a second emitting layer between the first emitting layer and the cathode, wherein the first emitting layer has at least one group represented by the following formula (11) and contains a first compound represented by the following formula (1A) as a first host material, the second emitting layer contains a second compound represented by the following formula (2) as a second host material, and the first emitting layer is in direct contact with the second emitting layer.
In the formula (1A):
In the formula (2):
In the first compound represented by the formula (1A) and the second compound represented by the formula (2):
A further aspect of the invention provides an electronic device including the organic electroluminescence device according to the above aspect of the invention.
A further aspect of the invention can provide a compound that can improve luminous efficiency, an organic EL device produced using the compound, and an electronic device including the organic EL device.
The above aspect of the invention can also provide an organic electroluminescence device with improved performance. The above aspect of the invention can also provide an organic electroluminescence device with improved luminous efficiency. The above aspect of the invention can also provide an electronic device including the organic electroluminescence device.
Herein, hydrogen atoms include isotopes with different numbers of neutrons, that is, protium, deuterium, and tritium.
Herein, in chemical structural formulae, a hydrogen atom, that is, a protium atom, a deuterium atom, or a tritium atom is bonded at a bonding position without symbols, such as “R” or “D”, which represents a deuterium atom.
Herein, ring carbon atoms are carbon atoms among atoms constituting a ring of a compound with a structure in which the atoms are circularly bonded (for example, a monocyclic compound, a fused-ring compound, a cross-linked compound, a carbocyclic compound, or a heterocyclic compound). When the ring is substituted with a substituent, carbons of the substituent are not included in the ring carbon atoms. Unless otherwise specified, the same applies to the “ring carbon atoms” described below. For example, a benzene ring has 6 ring carbon atoms, a naphthalene ring has 10 ring carbon atoms, a pyridine ring has 5 ring carbon atoms, and a furan ring has 4 ring carbon atoms. For example, a 9,9-diphenylfluorenyl group has 13 ring carbon atoms, and a 9,9′-spirobifluorenyl group has 25 ring carbon atoms.
When a benzene ring is substituted, for example, with an alkyl group, carbon atoms of the alkyl group are not included in the ring carbon atoms of the benzene ring. Thus, the benzene ring substituted with the alkyl group has 6 ring carbon atoms. When a naphthalene ring is substituted, for example, with an alkyl group, carbon atoms of the alkyl group are not included in the ring carbon atoms of the naphthalene ring. Thus, the naphthalene ring substituted with the alkyl group has 10 ring carbon atoms.
Herein, ring atoms are atoms constituting a ring of a compound (for example, a monocyclic compound, a fused-ring compound, a cross-linked compound, a carbocyclic compound, or a heterocyclic compound) with a structure in which the atoms are circularly bonded (for example, a monocyclic ring, a fused ring, or polycyclic). Atoms that do not constitute a ring (for example, a hydrogen atom that terminates a bond of an atom constituting the ring) and atoms of a substituent substituting a ring are not included in ring atoms. Unless otherwise specified, the same applies to the following “ring atoms”. For example, a pyridine ring has 6 ring atoms, a quinazoline ring has 10 ring atoms, and a furan ring has 5 ring atoms. For example, the number of hydrogen atoms bonded to a pyridine ring or the number of atoms constituting a substituent is not included in the number of pyridine ring atoms. Thus, a pyridine ring to which a hydrogen atom or a substituent is bonded has 6 ring atoms. For example, the number of hydrogen atoms bonded to carbon atoms of a quinazoline ring or the number of atoms constituting a substituent is not included in the number of quinazoline ring atoms. Thus, a quinazoline ring to which a hydrogen atom or a substituent is bonded has 10 ring atoms.
Herein, “XX to YY carbon atoms” of “a substituted or unsubstituted ZZ group having XX to YY carbon atoms” refers to the carbon atoms of the unsubstituted ZZ group and does not include the carbon atoms of a substituent when substituted. “YY” is larger than “XX”, “XX” represents an integer of 1 or more, and “YY” represents an integer of 2 or more.
Herein, “XX to YY atoms” of “a substituted or unsubstituted ZZ group having XX to YY atoms” refers to the atoms of the unsubstituted ZZ group and does not include the atoms of a substituent when substituted. “YY” is larger than “XX”, “XX” represents an integer of 1 or more, and “YY” represents an integer of 2 or more.
Herein, an unsubstituted ZZ group refers to an “unsubstituted ZZ group” of a “substituted or unsubstituted ZZ group”, and a substituted ZZ group refers to a “substituted ZZ group” of the “substituted or unsubstituted ZZ group”.
Herein, “unsubstituted” of a “substituted or unsubstituted ZZ group” means that a hydrogen atom of the ZZ group is not substituted with a substituent. A hydrogen atom in an “unsubstituted ZZ group” is a protium atom, a deuterium atom, or a tritium atom.
Herein, “substituted” of a “substituted or unsubstituted ZZ group” means that at least one hydrogen atom of the ZZ group is substituted with a substituent. Likewise, “substituted” of a “BB group substituted with an AA group” means that at least one hydrogen atom of the BB group is substituted with the AA group.
“Substituents Mentioned Herein”
Substituents mentioned herein are described below.
An “unsubstituted aryl group” mentioned herein has, unless otherwise specified herein, 6 to 50, preferably 6 to 30, more preferably 6 to 18 ring carbon atoms.
An “unsubstituted heterocyclic group” mentioned herein has, unless otherwise specified herein, 5 to 50, preferably 5 to 30, more preferably 5 to 18 ring atoms.
An “unsubstituted alkyl group” mentioned herein has, unless otherwise specified herein, 1 to 50, preferably 1 to 20, more preferably 1 to 6 carbon atoms.
An “unsubstituted alkenyl group” mentioned herein has, unless otherwise specified herein, 2 to 50, preferably 2 to 20, more preferably 2 to 6 carbon atoms.
An “unsubstituted alkynyl group” mentioned herein has, unless otherwise specified herein, 2 to 50, preferably 2 to 20, more preferably 2 to 6 carbon atoms.
An “unsubstituted cycloalkyl group” mentioned herein has, unless otherwise specified herein, 3 to 50, preferably 3 to 20, more preferably 3 to 6 ring carbon atoms.
An “unsubstituted arylene group” mentioned herein has, unless otherwise specified herein, 6 to 50, preferably 6 to 30, more preferably 6 to 18 ring carbon atoms.
An “unsubstituted divalent heterocyclic group” mentioned herein has, unless otherwise specified herein, 5 to 50, preferably 5 to 30, more preferably 5 to 18 ring atoms.
An “unsubstituted alkylene group” mentioned herein has, unless otherwise specified herein, 1 to 50, preferably 1 to 20, more preferably 1 to 6 carbon atoms.
Specific examples (specific example group G1) of the “substituted or unsubstituted aryl group” mentioned herein include unsubstituted aryl groups (specific example group G1A) below and substituted aryl groups (specific example group G1B) below. (Herein, an unsubstituted aryl group refers to an “unsubstituted aryl group” in a “substituted or unsubstituted aryl group”, and a substituted aryl group refers to a “substituted aryl group” in a “substituted or unsubstituted aryl group.”) A simply termed “aryl group” herein includes both of an “unsubstituted aryl group” and a “substituted aryl group.”
The “substituted aryl group” refers to a group derived by substituting at least one hydrogen atom in an “unsubstituted aryl group” with a substituent. Examples of the “substituted aryl group” include a group derived by substituting at least one hydrogen atom in the “unsubstituted aryl group” in the specific example group G1A below with a substituent, and examples of the substituted aryl group in the specific example group G1B below. It should be noted that the examples of the “unsubstituted aryl group” and the “substituted aryl group” mentioned herein are merely exemplary, and the “substituted aryl group” mentioned herein includes a group derived by further substituting a hydrogen atom bonded to a carbon atom of a skeleton of a “substituted aryl group” in the specific example group G1B below, and a group derived by further substituting a hydrogen atom of a substituent of the “substituted aryl group” in the specific example group G1B below.
a phenyl group, a p-biphenyl group, a m-biphenyl group, an o-biphenyl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, a m-terphenyl-4-yl group, a m-terphenyl-3-yl group, a m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a benzoanthryl group, a phenanthryl group, a benzophenanthryl group, a phenalenyl group, a pyrenyl group, a chrysenyl group, a benzochrysenyl group, a triphenylenyl group, a benzotriphenylenyl group, a tetracenyl group, a pentacenyl group, a fluorenyl group, a 9,9′-spirobifluorenyl group, a benzofluorenyl group, a benzofluorenyl group, a fluoranthenyl group, a benzofluoranthenyl group, a perylenyl group, and a monovalent aryl group derived by removing one hydrogen atom from ring structures represented by the following formulae (TEMP-1) to (TEMP-15).
an o-tolyl group, a m-tolyl group, a p-tolyl group, a para-xylyl group, a meta-xylyl group, an ortho-xylyl group, a para-isopropylphenyl group, a meta-isopropylphenyl group, an ortho-isopropylphenyl group, a para-t-butylphenyl group, a meta-t-butylphenyl group, an ortho-t-butylphenyl group, a 3,4,5-trimethylphenyl group, a 9,9-dimethylfluorenyl group, a 9,9-diphenylfluorenyl group, a 9,9-bis(4-methyl phenyl)fluorenyl group, a 9,9-bis(4-isopropylphenyl)fluorenyl group, a 9,9-bis(4-t-butylphenyl)fluorenyl group, a cyanophenyl group, a triphenylsilylphenyl group, a trimethylsilylphenyl group, a phenylnaphthyl group, a naphthylphenyl group, and a group derived by substituting at least one hydrogen atom of a monovalent group derived from the cyclic structures represented by the formulae (TEMP-1) to (TEMP-15) with a substituent.
The “heterocyclic group” mentioned herein refers to a cyclic group having at least one hetero atom in the ring atoms. Specific examples of the hetero atom include a nitrogen atom, oxygen atom, sulfur atom, silicon atom, phosphorus atom, and boron atom.
The “heterocyclic group” mentioned herein is a monocyclic group or a fused-ring group.
The “heterocyclic group” mentioned herein is an aromatic heterocyclic group or a non-aromatic heterocyclic group.
Specific examples (specific example group G2) of the “substituted or unsubstituted heterocyclic group” mentioned herein include unsubstituted heterocyclic groups (specific example group G2A) and substituted heterocyclic groups (specific example group G2B). (Herein, an unsubstituted heterocyclic group refers to an “unsubstituted heterocyclic group” in a “substituted or unsubstituted heterocyclic group,” and a substituted heterocyclic group refers to a “substituted heterocyclic group” in a “substituted or unsubstituted heterocyclic group.”) A simply termed “heterocyclic group” herein includes both of “unsubstituted heterocyclic group” and “substituted heterocyclic group.”
The “substituted heterocyclic group” refers to a group derived by substituting at least one hydrogen atom in an “unsubstituted heterocyclic group” with a substituent. Specific examples of the “substituted heterocyclic group” include a group derived by substituting at least one hydrogen atom in the “unsubstituted heterocyclic group” in the specific example group G2A below with a substituent, and examples of the substituted heterocyclic group in the specific example group G2B below. It should be noted that the examples of the “unsubstituted heterocyclic group” and the “substituted heterocyclic group” mentioned herein are merely exemplary, and the “substituted heterocyclic group” mentioned herein includes a group derived by further substituting a hydrogen atom bonded to a ring atom of a skeleton of a “substituted heterocyclic group” in the specific example group G2B below, and a group derived by further substituting a hydrogen atom of a substituent of the “substituted heterocyclic group” in the specific example group G2B below.
The specific example group G2A includes, for instance, unsubstituted heterocyclic groups including a nitrogen atom (specific example group G2A1) below, unsubstituted heterocyclic groups including an oxygen atom (specific example group G2A2) below, unsubstituted heterocyclic groups including a sulfur atom (specific example group G2A3) below, and monovalent heterocyclic groups (specific example group G2A4) derived by removing a hydrogen atom from cyclic structures represented by formulae (TEMP-16) to (TEMP-33) below.
The specific example group G2B includes, for instance, substituted heterocyclic groups including a nitrogen atom (specific example group G2B1) below, substituted heterocyclic groups including an oxygen atom (specific example group G2B2) below, substituted heterocyclic groups including a sulfur atom (specific example group G2B3) below, and groups derived by substituting at least one hydrogen atom of the monovalent heterocyclic groups (specific example group G2B4) derived from the cyclic structures represented by formulae (TEMP-16) to (TEMP-33) below.
a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a pyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an indolyl group, an isoindolyl group, an indolizinyl group, a quinolizinyl group, a quinolyl group, an isoquinolyl group, a cinnolyl group, a phthalazinyl group, a quinazolinyl group, a quinoxalinyl group, a benzimidazolyl group, an indazolyl group, a phenanthrolinyl group, a phenanthridinyl group, an acridinyl group, a phenazinyl group, a carbazolyl group, a benzocarbazolyl group, a morpholino group, a phenoxazinyl group, a phenothiazinyl group, an azacarbazolyl group, and a diazacarbazolyl group.
a furyl group, an oxazolyl group, an isoxazolyl group, an oxadiazolyl group, a xanthenyl group, a benzofuranyl group, an isobenzofuranyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, a benzoxazolyl group, a benzoisoxazolyl group, a phenoxazinyl group, a morpholino group, a dinaphthofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, an azanaphthobenzofuranyl group, and a diazanaphthobenzofuranyl group.
a thienyl group, a thiazolyl group, an isothiazolyl group, a thiadiazolyl group, a benzothiophenyl group (benzothienyl group), an isobenzothiophenyl group (isobenzothienyl group), a dibenzothiophenyl group (dibenzothienyl group), a naphthobenzothiophenyl group (naphthobenzothienyl group), a benzothiazolyl group, a benzoisothiazolyl group, a phenothiazinyl group, a dinaphthothiophenyl group (dinaphthothienyl group), an azadibenzothiophenyl group (azadibenzothienyl group), a diazadibenzothiophenyl group (diazadibenzothienyl group), an azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and a diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).
Monovalent Heterocyclic Groups Derived by Removing One Hydrogen Atom from Cyclic Structures Represented by Formulae (TEMP-16) to (TEMP-33) (Specific Example Group G2A4):
In the formulae (TEMP-16) to (TEMP-33), XA and YA each independently represent an oxygen atom, a sulfur atom, NH, or CH2. At least one of XA or YA represents an oxygen atom, a sulfur atom, or NH.
In the formulae (TEMP-16) to (TEMP-33), when at least one of XA or YA represents NH or CH2, a monovalent heterocyclic group derived from the ring structures represented by the formulae (TEMP-16) to (TEMP-33) includes a monovalent group derived by removing one hydrogen atom from the NH or CH2.
a (9-phenyl)carbazolyl group, a (9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a (9-naphthyl)carbazolyl group, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a methylbenzimidazolyl group, an ethylbenzimidazolyl group, a phenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinyl group, a phenylquinazolinyl group, and a biphenylylquinazolinyl group.
a phenyldibenzofuranyl group, a methyldibenzofuranyl group, a t-butyldibenzofuranyl group, and a monovalent residue of spiro[9H-xanthene-9,9′-[9H]fluorene].
a phenyldibenzothiophenyl group, a methyldibenzothiophenyl group, a t-butyldibenzothiophenyl group, and a monovalent residue of spiro[9H-thioxanthene-9,9′-[9H]fluorene].
Groups Obtained by Substituting at Least One Hydrogen Atom of Monovalent Heterocyclic Group Derived from Cyclic Structures Represented by Formulae (TEMP-16) to (TEMP-33) with Substituent (Specific Example Group G2B4):
The “at least one hydrogen atom of a monovalent heterocyclic group” means at least one hydrogen atom selected from a hydrogen atom bonded to a ring carbon atom of the monovalent heterocyclic group, a hydrogen atom bonded to a nitrogen atom of at least one of XA or YA in a form of NH, and a hydrogen atom of one of XA and YA in a form of a methylene group (CH2).
Specific examples (specific example group G3) of the “substituted or unsubstituted alkyl group” mentioned herein include unsubstituted alkyl groups (specific example group G3A) and substituted alkyl groups (specific example group G3B) below. (Herein, an unsubstituted alkyl group refers to an “unsubstituted alkyl group” in a “substituted or unsubstituted alkyl group,” and a substituted alkyl group refers to a “substituted alkyl group” in a “substituted or unsubstituted alkyl group.”) A simply termed “alkyl group” herein includes both of “unsubstituted alkyl group” and “substituted alkyl group.”
The “substituted alkyl group” refers to a group derived by substituting at least one hydrogen atom in an “unsubstituted alkyl group” with a substituent. Specific examples of the “substituted alkyl group” include a group derived by substituting at least one hydrogen atom of an “unsubstituted alkyl group” (specific example group G3A) below with a substituent, and examples of the substituted alkyl group (specific example group G3B) below. Herein, the alkyl group for the “unsubstituted alkyl group” refers to a chain alkyl group. Accordingly, the “unsubstituted alkyl group” include linear “unsubstituted alkyl group” and branched “unsubstituted alkyl group.” It should be noted that the examples of the “unsubstituted alkyl group” and the “substituted alkyl group” mentioned herein are merely exemplary, and the “substituted alkyl group” mentioned herein includes a group derived by further substituting a hydrogen atom of a skeleton of the “substituted alkyl group” in the specific example group G3B, and a group derived by further substituting a hydrogen atom of a substituent of the “substituted alkyl group” in the specific example group G3B.
a methyl group, an ethyl group, a n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a s-butyl group, and a t-butyl group.
a heptafluoropropyl group (including isomers), a pentafluoroethyl group, a 2,2,2-trifluoroethyl group, and a trifluoromethyl group.
Specific examples (specific example group G4) of the “substituted or unsubstituted alkenyl group” mentioned herein include unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B). (Herein, an unsubstituted alkenyl group refers to an “unsubstituted alkenyl group” in a “substituted or unsubstituted alkenyl group,” and a substituted alkenyl group refers to a “substituted alkenyl group” in a “substituted or unsubstituted alkenyl group.”) A simply termed “alkenyl group” herein includes both of “unsubstituted alkenyl group” and “substituted alkenyl group.”
The “substituted alkenyl group” refers to a group derived by substituting at least one hydrogen atom in an “unsubstituted alkenyl group” with a substituent. Specific examples of the “substituted alkenyl group” include an “unsubstituted alkenyl group” (specific example group G4A) substituted by a substituent, and examples of the substituted alkenyl group (specific example group G4B) below. It should be noted that the examples of the “unsubstituted alkenyl group” and the “substituted alkenyl group” mentioned herein are merely exemplary, and the “substituted alkenyl group” mentioned herein includes a group derived by further substituting a hydrogen atom of a skeleton of the “substituted alkenyl group” in the specific example group G4B with a substituent, and a group derived by further substituting a hydrogen atom of a substituent of the “substituted alkenyl group” in the specific example group G4B with a substituent.
a vinyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, and a 3-butenyl group.
a 1,3-butanedienyl group, a 1-methylvinyl group, a 1-methylallyl group, a 1,1-dimethylallyl group, a 2-methylallyl group, and a 1,2-dimethylallyl group.
Specific examples (specific example group G5) of the “substituted or unsubstituted alkynyl group” mentioned herein include unsubstituted alkynyl groups (specific example group G5A) below. (Herein, an unsubstituted alkynyl group refers to an “unsubstituted alkynyl group” in a “substituted or unsubstituted alkynyl group.”) A simply termed “alkynyl group” herein includes both of “unsubstituted alkynyl group” and “substituted alkynyl group.”
The “substituted alkynyl group” refers to a group derived by substituting at least one hydrogen atom in an “unsubstituted alkynyl group” with a substituent. Specific examples of the “substituted alkynyl group” include a group derived by substituting at least one hydrogen atom of the “unsubstituted alkynyl group” (specific example group G5A) below with a substituent.
Specific examples (specific example group G6) of the “substituted or unsubstituted cycloalkyl group” mentioned herein include unsubstituted cycloalkyl groups (specific example group G6A) and substituted cycloalkyl groups (specific example group G6B). (Herein, an unsubstituted cycloalkyl group refers to an “unsubstituted cycloalkyl group” in a “substituted or unsubstituted cycloalkyl group,” and a substituted cycloalkyl group refers to a “substituted cycloalkyl group” in a “substituted or unsubstituted cycloalkyl group.”) A simply termed “cycloalkyl group” herein includes both of “unsubstituted cycloalkyl group” and “substituted cycloalkyl group.”
The “substituted cycloalkyl group” refers to a group derived by substituting at least one hydrogen atom of an “unsubstituted cycloalkyl group” with a substituent. Specific examples of the “substituted cycloalkyl group” include a group derived by substituting at least one hydrogen atom of the “unsubstituted cycloalkyl group” (specific example group G6A) below with a substituent, and examples of the substituted cycloalkyl group (specific example group G6B) below. It should be noted that the examples of the “unsubstituted cycloalkyl group” and the “substituted cycloalkyl group” mentioned herein are merely exemplary, and the “substituted cycloalkyl group” mentioned herein includes a group derived by substituting at least one hydrogen atom bonded to a carbon atom of a skeleton of the “substituted cycloalkyl group” in the specific example group G6B with a substituent, and a group derived by further substituting a hydrogen atom of a substituent of the “substituted cycloalkyl group” in the specific example group G6B with a substituent.
a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-adamantyl group, a 2-adamantyl group, a 1-norbornyl group, and a 2-norbornyl group.
a 4-methylcyclohexyl group.
Group Represented by —Si(R901)(R902)(R903)
Specific examples (specific example group G7) of the group represented herein by —Si(R901)(R902)(R903) include: —Si(G1)(G1)(G1), —Si(G1)(G2)(G2), —Si(G1)(G1)(G2), —Si(G2)(G2)(G2), —Si(G3)(G3)(G3), and —Si(G6)(G6)(G6).
A plurality of G1 in —Si(G1)(G1)(G1) are mutually the same or different.
A plurality of G2 in —Si(G1)(G2)(G2) are mutually the same or different.
A plurality of G1 in —Si(G1)(G1)(G2) are mutually the same or different.
A plurality of G2 in —Si(G2)(G2)(G2) are mutually the same or different.
A plurality of G3 in —Si(G3)(G3)(G3) are mutually the same or different.
A plurality of G6 in —Si(G6)(G6)(G6) are mutually the same or different.
Specific examples (specific example group G8) of a group represented by —O—(R904) herein include: —O(G1), —O(G2), —O(G3), and —O(G6).
Specific examples (specific example group G9) of a group represented herein by —S—(R905) include: —S(G1), —S(G2), —S(G3), and —S(G6).
Specific examples (specific example group G10) of a group represented herein by —N(R906)(R907) include: —N(G1)(G1), —N(G2)(G2), —N(G1)(G2), —N(G3)(G3), and —N(G6)(G6).
A plurality of G1 in —N(G1)(G1) are mutually the same or different.
A plurality of G2 in —N(G2)(G2) are mutually the same or different.
A plurality of G3 in —N(G3)(G3) are mutually the same or different.
A plurality of G6 in —N(G6)(G6) are mutually the same or different.
Specific examples (specific example group G11) of “halogen atom” mentioned herein include a fluorine atom, chlorine atom, bromine atom, and iodine atom.
The “substituted or unsubstituted fluoroalkyl group” mentioned herein refers to a group derived by substituting at least one hydrogen atom bonded to at least one of carbon atoms forming an alkyl group in the “substituted or unsubstituted alkyl group” with a fluorine atom, and also includes a group (perfluoro group) derived by substituting all of hydrogen atoms bonded to carbon atoms forming the alkyl group in the “substituted or unsubstituted alkyl group” with fluorine atoms. An “unsubstituted fluoroalkyl group” has, unless otherwise specified herein, 1 to 50, preferably 1 to 30, more preferably 1 to 18 carbon atoms. The “substituted fluoroalkyl group” refers to a group derived by substituting at least one hydrogen atom in a “fluoroalkyl group” with a substituent. It should be noted that the examples of the “substituted fluoroalkyl group” mentioned herein include a group derived by further substituting at least one hydrogen atom bonded to a carbon atom of an alkyl chain of a “substituted fluoroalkyl group” with a substituent, and a group derived by further substituting at least one hydrogen atom of a substituent of the “substituted fluoroalkyl group” with a substituent. Specific examples of the “substituted fluoroalkyl group” include a group derived by substituting at least one hydrogen atom of the “alkyl group” (specific example group G3) with a fluorine atom.
The “substituted or unsubstituted haloalkyl group” mentioned herein refers to a group derived by substituting at least one hydrogen atom bonded to carbon atoms forming the alkyl group in the “substituted or unsubstituted alkyl group” with a halogen atom, and also includes a group derived by substituting all hydrogen atoms bonded to carbon atoms forming the alkyl group in the “substituted or unsubstituted alkyl group” with halogen atoms. An “unsubstituted haloalkyl group” has, unless otherwise specified herein, 1 to 50, preferably 1 to 30, more preferably 1 to 18 carbon atoms. The “substituted haloalkyl group” refers to a group derived by substituting at least one hydrogen atom in a “haloalkyl group” with a substituent. It should be noted that the examples of the “substituted haloalkyl group” mentioned herein include a group derived by further substituting at least one hydrogen atom bonded to a carbon atom of an alkyl chain of a “substituted haloalkyl group” with a substituent, and a group derived by further substituting at least one hydrogen atom of a substituent of the “substituted haloalkyl group” with a substituent. Specific examples of the “unsubstituted haloalkyl group” include a group derived by substituting at least one hydrogen atom of the “alkyl group” (specific example group G3) with a halogen atom. The haloalkyl group is sometimes referred to as a halogenated alkyl group.
Specific examples of a “substituted or unsubstituted alkoxy group” mentioned herein include a group represented by —O(G3), G3 being the “substituted or unsubstituted alkyl group” in the specific example group G3. An “unsubstituted alkoxy group” has, unless otherwise specified herein, 1 to 50, preferably 1 to 30, more preferably 1 to 18 carbon atoms.
Specific examples of a “substituted or unsubstituted alkylthio group” mentioned herein include a group represented by —S(G3), G3 being the “substituted or unsubstituted alkyl group” in the specific example group G3. An “unsubstituted alkylthio group” has, unless otherwise specified herein, 1 to 50, preferably 1 to 30, more preferably 1 to 18 carbon atoms.
Specific examples of a “substituted or unsubstituted aryloxy group” mentioned herein include a group represented by —O(G1), G1 being the “substituted or unsubstituted aryl group” in the specific example group G1. An “unsubstituted aryloxy group” has, unless otherwise specified herein, 6 to 50, preferably 6 to 30, more preferably 6 to 18 ring carbon atoms.
Specific examples of a “substituted or unsubstituted arylthio group” mentioned herein include a group represented by —S(G1), G1 being the “substituted or unsubstituted aryl group” in the specific example group G1. An “unsubstituted arylthio group” has, unless otherwise specified herein, 6 to 50, preferably 6 to 30, more preferably 6 to 18 ring carbon atoms.
Specific examples of a “trialkylsilyl group” mentioned herein include a group represented by —Si(G3)(G3)(G3), G3 being the “substituted or unsubstituted alkyl group” in the specific example group G3. The plurality of G3 in —Si(G3)(G3)(G3) are mutually the same or different. Each of the alkyl groups in the “trialkylsilyl group” has, unless otherwise specified herein, 1 to 50, preferably 1 to 20, more preferably 1 to 6 carbon atoms.
Specific examples of a “substituted or unsubstituted aralkyl group” mentioned herein include a group represented by (G3)-(G1), G3 being the “substituted or unsubstituted alkyl group” in the specific example group G3, G1 being the “substituted or unsubstituted aryl group” in the specific example group G1. Accordingly, the “aralkyl group” is a group derived by substituting a hydrogen atom of the “alkyl group” with a substituent in a form of the “aryl group,” which is an example of the “substituted alkyl group.” An “unsubstituted aralkyl group,” which is an “unsubstituted alkyl group” substituted by an “unsubstituted aryl group,” has, unless otherwise specified herein, 7 to 50 carbon atoms, preferably 7 to 30 carbon atoms, more preferably 7 to 18 carbon atoms.
Specific examples of the “substituted or unsubstituted aralkyl group” include a benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, a-naphthylmethyl group, 1-a-naphthylethyl group, 2-a-naphthylethyl group, 1-a-naphthylisopropyl group, 2-a-naphthylisopropyl group, p-naphthylmethyl group, 1-p-naphthylethyl group, 2-p-naphthylethyl group, 1-p-naphthylisopropyl group, and 2-p-naphthylisopropyl group.
Preferable examples of the substituted or unsubstituted aryl group mentioned herein include, unless otherwise specified herein, a phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, phenanthryl group, pyrenyl group, chrysenyl group, triphenylenyl group, fluorenyl group, 9,9′-spirobifluorenyl group, 9,9-dimethylfluorenyl group, and 9,9-diphenylfluorenyl group.
Preferable examples of the substituted or unsubstituted heterocyclic group mentioned herein include, unless otherwise specified herein, a pyridyl group, pyrimidinyl group, triazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, benzimidazolyl group, phenanthrolinyl group, carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, or 9-carbazolyl group), benzocarbazolyl group, azacarbazolyl group, diazacarbazolyl group, dibenzofuranyl group, naphthobenzofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, dibenzothiophenyl group, naphthobenzothiophenyl group, azadibenzothiophenyl group, diazadibenzothiophenyl group, (9-phenyl)carbazolyl group ((9-phenyl)carbazole-1-yl group, (9-phenyl)carbazole-2-yl group, (9-phenyl)carbazole-3-yl group, or (9-phenyl)carbazole-4-yl group), (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, diphenylcarbazole-9-yl group, phenylcarbazole-9-yl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group.
The carbazolyl group mentioned herein is, unless otherwise specified herein, specifically a group represented by one of formulae below.
The (9-phenyl)carbazolyl group mentioned herein is, unless otherwise specified herein, specifically a group represented by one of formulae below.
In the formulae (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.
The dibenzofuranyl group and dibenzothiophenyl group mentioned herein are, unless otherwise specified herein, each specifically represented by one of formulae below.
In the formulae (TEMP-34) to (TEMP-41), * represents a bonding position.
Preferable examples of the substituted or unsubstituted alkyl group mentioned herein include, unless otherwise specified herein, a methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, and t-butyl group.
The “substituted or unsubstituted arylene group” mentioned herein is, unless otherwise specified herein, a divalent group derived by removing one hydrogen atom on an aryl ring of the “substituted or unsubstituted aryl group.” Specific examples of the “substituted or unsubstituted arylene group” (specific example group G12) include a divalent group derived by removing one hydrogen atom on an aryl ring of the “substituted or unsubstituted aryl group” in the specific example group G1.
The “substituted or unsubstituted divalent heterocyclic group” mentioned herein is, unless otherwise specified herein, a divalent group derived by removing one hydrogen atom on a heterocycle of the “substituted or unsubstituted heterocyclic group.” Specific examples of the “substituted or unsubstituted divalent heterocyclic group” (specific example group G13) include a divalent group derived by removing one hydrogen atom on a heterocyclic ring of the “substituted or unsubstituted heterocyclic group” in the specific example group G2.
The “substituted or unsubstituted alkylene group” mentioned herein is, unless otherwise specified herein, a divalent group derived by removing one hydrogen atom on an alkyl chain of the “substituted or unsubstituted alkyl group.” Specific examples of the “substituted or unsubstituted alkylene group” (specific example group G14) include a divalent group derived by removing one hydrogen atom on an alkyl chain of the “substituted or unsubstituted alkyl group” in the specific example group G3.
The substituted or unsubstituted arylene group mentioned herein is, unless otherwise specified herein, preferably any one of groups represented by formulae (TEMP-42) to (TEMP-68) below.
In the formulae (TEMP-42) to (TEMP-52), Q1 to Q10 each independently represent a hydrogen atom or a substituent.
In the formulae (TEMP-42) to (TEMP-52), * represents a bonding position.
In the formulae (TEMP-53) to (TEMP-62), Q1 to Q10 each independently represent a hydrogen atom or a substituent.
In the formulae, Q9 and Q10 may be mutually bonded through a single bond to form a ring.
In the formulae (TEMP-53) to (TEMP-62), * represents a bonding position.
In the formulae (TEMP-63) to (TEMP-68), Q1 to Q8 each independently represent a hydrogen atom or a substituent.
In the formulae (TEMP-63) to (TEMP-68), * represents a bonding position.
The substituted or unsubstituted divalent heterocyclic group mentioned herein is, unless otherwise specified herein, preferably a group represented by any one of formulae (TEMP-69) to (TEMP-102) below.
In the formulae (TEMP-69) to (TEMP-82), Q1 to Q9 each independently represent a hydrogen atom or a substituent.
In the formulae (TEMP-83) to (TEMP-102), Q1 to Q8 are each independently a hydrogen atom or a substituent.
The above has described “Substituents in the present description”.
Instances where “at least one combination of adjacent two or more (of . . . ) are mutually bonded to form a substituted or unsubstituted monocyclic ring, mutually bonded to form a substituted or unsubstituted fused ring, or not mutually bonded” mentioned herein refer to instances where “at least one combination of adjacent two or more (of . . . ) are mutually bonded to form a substituted or unsubstituted monocyclic ring, “at least one combination of adjacent two or more (of . . . ) are mutually bonded to form a substituted or unsubstituted fused ring,” and “at least one combination of adjacent two or more (of . . . ) are not mutually bonded.”
Instances where “at least one combination of adjacent two or more (of . . . ) are mutually bonded to form a substituted or unsubstituted monocyclic ring” and “at least one combination of adjacent two or more (of . . . ) are mutually bonded to form a substituted or unsubstituted fused ring” mentioned herein (these instances will be sometimes collectively referred to as an instance of “bonded to form a ring” hereinafter) will be described below. An anthracene compound having a basic skeleton in a form of an anthracene ring and represented by a formula (TEMP-103) below will be used as an example for the description.
For instance, when “at least one combination of adjacent two or more of R921 to R930 are mutually bonded to form a ring,” the combination of adjacent ones of R921 to R930 (i.e. the combination at issue) is a combination of R921 and R922, a combination of R922 and R923, a combination of R923 and R924, a combination of R924 and R930, a combination of R930 and R925, a combination of R925 and R926, a combination of R926 and R927, a combination of R927 and R928, a combination of R928 and R929, or a combination of R929 and R921.
The term “at least one combination” means that two or more of the above combinations of adjacent two or more of R921 to R930 may simultaneously form rings. For instance, when R921 and R922 are mutually bonded to form a ring QA and R925 and R926 are simultaneously mutually bonded to form a ring QB, the anthracene compound represented by the formula (TEMP-103) is represented by a formula (TEMP-104) below.
The instance where the “combination of adjacent two or more” form a ring means not only an instance where the “two” adjacent components are bonded but also an instance where adjacent “three or more” are bonded. For instance, R921 and R922 are mutually bonded to form a ring QA and R922 and R923 are mutually bonded to form a ring QC, and mutually adjacent three components (R921, R922 and R923) are mutually bonded to form a ring fused to the anthracene basic skeleton. In this case, the anthracene compound represented by the formula (TEMP-103) is represented by a formula (TEMP-105) below. In the formula (TEMP-105) below, the ring QA and the ring QC share R922.
The formed “monocyclic ring” or “fused ring” may be, in terms of the formed ring in itself, a saturated ring or an unsaturated ring. When the “combination of adjacent two” form a “monocyclic ring” or a “fused ring,” the “monocyclic ring” or “fused ring” may be a saturated ring or an unsaturated ring. For instance, the ring QA and the ring QB formed in the formula (TEMP-104) are each independently a “monocyclic ring” or a “fused ring.” Further, the ring QA and the ring QC formed in the formula (TEMP-105) are each a “fused ring.” The ring QA and the ring QC in the formula (TEMP-105) are fused to form a fused ring. When the ring QA in the formula (TEMP-104) is a benzene ring, the ring QA is a monocyclic ring. When the ring QA in the formula (TEMP-104) is a naphthalene ring, the ring QA is a fused ring.
The “unsaturated ring” represents an aromatic hydrocarbon ring or an aromatic heterocycle. The “saturated ring” represents an aliphatic hydrocarbon ring or a non-aromatic heterocycle.
Specific examples of the aromatic hydrocarbon ring include a ring formed by terminating a bond of a group in the specific example of the specific example group G1 with a hydrogen atom.
Specific examples of the aromatic heterocycle include a ring formed by terminating a bond of an aromatic heterocyclic group in the specific example of the specific example group G2 with a hydrogen atom.
Specific examples of the aliphatic hydrocarbon ring include a ring formed by terminating a bond of a group in the specific example of the specific example group G6 with a hydrogen atom.
To “form a ring” herein means that a ring is formed only by a plurality of atoms of a basic skeleton, or by a combination of a plurality of atoms of the basic skeleton and one or more optional atoms. For instance, the ring QA formed by mutually bonding R921 and R922 shown in the formula (TEMP-104) is a ring formed by a carbon atom of the anthracene skeleton bonded to R921, a carbon atom of the anthracene skeleton bonded to R922, and one or more optional atoms. Specifically, when the ring QA is formed by R921 and R922, the ring formed by a carbon atom of the anthracene skeleton bonded to R921, a carbon atom of the anthracene skeleton bonded to R922, and four carbon atoms is a benzene ring.
The “optional atom” is, unless otherwise specified herein, preferably at least one atom selected from the group consisting of a carbon atom, nitrogen atom, oxygen atom, and sulfur atom. A bond of the optional atom (e.g. a carbon atom and a nitrogen atom) not forming a ring may be terminated by a hydrogen atom or the like or may be substituted by an “optional substituent” described later. When the ring includes an optional element other than carbon atom, the resultant ring is a heterocycle.
The number of “one or more optional atoms” forming the monocyclic ring or fused ring is, unless otherwise specified herein, preferably in a range from 2 to 15, more preferably in a range from 3 to 12, further preferably in a range from 3 to 5.
Unless otherwise specified herein, the ring, which may be a “monocyclic ring” or “fused ring,” is preferably a “monocyclic ring.”
Unless otherwise specified herein, the ring, which may be a “saturated ring” or “unsaturated ring,” is preferably an “unsaturated ring.”
Unless otherwise specified herein, the “monocyclic ring” is preferably a benzene ring.
Unless otherwise specified herein, the “unsaturated ring” is preferably a benzene ring.
When “at least one combination of adjacent two or more” (of . . . ) are “mutually bonded to form a substituted or unsubstituted monocyclic ring” or “mutually bonded to form a substituted or unsubstituted fused ring,” unless otherwise specified herein, at least one combination of adjacent two or more of components are preferably mutually bonded to form a substituted or unsubstituted “unsaturated ring” formed of a plurality of atoms of the basic skeleton, and 1 to 15 atoms of at least one element selected from the group consisting of carbon, nitrogen, oxygen and sulfur.
When the “monocyclic ring” or the “fused ring” has a substituent, the substituent is the substituent described in later-described “optional substituent.” When the “monocyclic ring” or the “fused ring” has a substituent, specific examples of the substituent are the substituents described in the above under the subtitle “Substituent Mentioned Herein.”
When the “saturated ring” or the “unsaturated ring” has a substituent, the substituent is the substituent described in later-described “optional substituent.” When the “monocyclic ring” or the “fused ring” has a substituent, specific examples of the substituent are the substituents described in the above under the subtitle “Substituent Mentioned Herein.”
The above is the description for the instances where “at least one combination of adjacent two or more (of . . . ) are mutually bonded to form a substituted or unsubstituted monocyclic ring” and “at least one combination of adjacent two or more (of . . . ) are mutually bonded to form a substituted or unsubstituted fused ring” mentioned herein (sometimes referred to as an instance of “bonded to form a ring”).
In an exemplary embodiment herein, a substituent for the substituted or unsubstituted group (sometimes referred to as an “optional substituent” hereinafter) is, for instance, a group selected from the group consisting of an unsubstituted alkyl group, having 1 to 50 carbon atoms, unsubstituted alkenyl group, having 2 to 50 carbon atoms, unsubstituted alkynyl group, having 2 to 50 carbon atoms, unsubstituted cycloalkyl group, having 3 to 50 ring carbon atoms, —Si(R901)(R902)(R903), —O—(R904), —S—(R905), —N(R906)(R907), a halogen atom, a cyano group, a nitro group, unsubstituted aryl group, having 6 to 50 ring carbon atoms, and unsubstituted heterocyclic group, having 5 to 50 ring atoms,
In an exemplary embodiment, a substituent for the substituted or unsubstituted group is selected from the group consisting of alkyl group, having 1 to 50 carbon atoms, aryl group, having 6 to 50 ring carbon atoms, and heterocyclic group, having 5 to 50 ring atoms.
In an exemplary embodiment, a substituent for the “substituted or unsubstituted group” is selected from the group consisting of alkyl group, having 1 to 18 carbon atoms, aryl group, having 6 to 18 ring carbon atoms, and heterocyclic group, having 5 to 18 ring atoms.
Specific examples of the above optional substituent are the same as the specific examples of the substituent described in the above under the subtitle “Substituent Mentioned Herein.”
Unless otherwise specified herein, adjacent ones of the optional substituents may form a “saturated ring” or an “unsaturated ring,” preferably a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, more preferably a benzene ring.
Unless otherwise specified herein, the optional substituent may further include a substituent. Examples of the substituent for the optional substituent are the same as the examples of the optional substituent.
Herein, numerical ranges represented by “AA to BB” represent a range whose lower limit is the value (AA) recited before “to” and whose upper limit is the value (BB) recited after “to.”
First Compound
An organic EL device according to an exemplary embodiment of the invention has a first emitting layer containing a first compound. The first compound is a compound represented by the following formula (1A).
A compound according to a first exemplary embodiment (a compound represented by the formula (12X)) described later, a compound according to a second exemplary embodiment (a compound represented by the formula (120)), and a compound according to a third exemplary embodiment (a compound represented by the formula (1), (2), or (3)) are examples of a compound represented by the following formula (1A).
In the formula (1A):
R101 to R110 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R801, a group represented by —COOR802, a halogen atom, a cyano group, a nitro group, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or a group represented by the formula (11),
The compound according to the first exemplary embodiment is a compound represented by the following formula (12X).
The compound according to the first exemplary embodiment (a compound represented by the following formula (12X)) is an example of the first compound (a compound that has at least one group represented by the formula (11) and is represented by the formula (1A)).
The compound according to the first exemplary embodiment is a compound in which R101 in the formula (1A) of the first compound is bonded to the formula (11).
[Formula 33]
Py1-L1-L2-Py2 (12X)
In the formula (12X):
A substituent F for “substituted or unsubstituted” in the substituent E is each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9′-spirobifluorenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, or a substituted or unsubstituted 9,9-diphenylfluorenyl group.
In the formulae (13-1) to (13-6), R11 to R15 and R11A to R15A each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a group represented by —Si(Rx)(Ry)(Rz), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
In the formula (10-1), at least one combination of a combination of R11 and R12, a combination of R13 and R14, a combination of R21 and R22, or a combination of R23 and R24 are mutually bonded to form a substituted or unsubstituted monocyclic ring, are mutually bonded to form a substituted or unsubstituted fused ring, or are not mutually bonded,
In the formulae (20-1) and (30-1):
In the formula (4),
In the formulae (10-1), (20-1), and (30-1) and the formula (4), a substituent for “substituted or unsubstituted” in R11 to R14, R21 to R24, R31 to R34, R41 to R44, R51 to R54, R61 to R64, and R311 to R319 is each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9′-spirobifluorenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, or a substituted or unsubstituted 9,9-diphenylfluorenyl group.
A bispyrene bonded via one linker (a linking group) is known as a host material contained in the emitting layer. However, a bispyrene bonded via one linker tends to have a twisted molecular structure, tends to reduce the planarity of the whole compound, and may reduce hole transportability.
In contrast, a compound represented by the formula (12X) according to the first exemplary embodiment (hereinafter referred to as “the compound according to the first exemplary embodiment”) has a structure in which two 1-pyrenyl groups (Py1 and Py2) are bonded via -L1-L2- (two linkers composed of L1 serving as a linking group and L2 serving as a linking group), and -L1-L2- has an asymmetric structure. The compound according to the first exemplary embodiment with such a structure is less likely to have a twisted molecular structure, easily maintains the planarity of the whole compound, and improves hole transportability.
Thus, the compound according to the first exemplary embodiment contained in the emitting layer can improve luminous efficiency.
The compound according to the first exemplary embodiment has an asymmetric structure as a whole when -L1-L2- in the formula (12X) has an asymmetric structure.
In the first exemplary embodiment, that -L1-L2- in the formula (12X) has an asymmetric structure means that -L1-L2- in the formula (12X) has one of the following structures (asymmetric structures 1 to 4).
Asymmetric structure 1: L1 and L2 each independently represent a substituted or unsubstituted phenylene group, and the bonding position of the phenylene group in L1 is different from the bonding position of the phenylene group in L2.
Asymmetric structure 2: L1 and L2 each independently represent a substituted or unsubstituted naphthylene group, and the bonding position of the naphthylene group in L1 is different from the bonding position of the naphthylene group in L2.
Asymmetric structure 3: One of L1 and L2 represents a substituted or unsubstituted phenylene group, and the other of L1 and L2 represents a substituted or unsubstituted naphthylene group.
Asymmetric structure 4: Although L1 and L2 each independently represent a substituted or unsubstituted phenylene group, and the bonding position of the phenylene group in L1 is the same as the bonding position of the phenylene group in L2, the structure of L1 and the structure of L2 are mutually different including substituents.
First, the asymmetric structures 1 to 3 are described with respect to compounds represented by the following formulae (130X), (130Y), and (130Z) in which carbon positions are numbered.
Asymmetric Structure 1
Examples of -L1-L2- with the asymmetric structure 1 include groups represented by the formulae (13-1) to (13-6).
The asymmetric structure 1 is described with respect to the following formulae (130-1) to (130-3), which are examples of the groups represented by the formulae (13-1) to (13-3).
For example, a group represented by the following formula (130-1) has an asymmetric structure because the bonding position of *1 (No. 5 in the formula (130X)) is different from the bonding position of *2 (No. 6′ in the formula (130X)).
A group represented by the following formula (130-2) has an asymmetric structure because the bonding position of *1 (No. 5 in the formula (130X)) is different from the bonding position of *2 (No. 4′ in the formula (130X)).
A structure represented by the following formula (130-3) has an asymmetric structure because the bonding position of *1 (No. 4 in the formula (130X)) is different from the bonding position of *2 (No. 6′ in the formula (130X)).
Asymmetric Structure 2
Examples of -L1-L2- with the asymmetric structure 2 include groups represented by the formulae (13-49) to (13-69) described later in the second exemplary embodiment. The asymmetric structure 2 is described with respect to the following formulae (130-52) and (130-53), which are examples of the groups represented by the formulae (13-52) and (13-53) described later in the second exemplary embodiment.
For example, a group represented by the following formula (130-52) has an asymmetric structure because the bonding position of *1 (No. 4 in the formula (130Y)) is different from the bonding position of *2 (No. 5′ in the formula (130Y)), though the bonding position (No. 1 in the formula (130Y)) of L1 (a naphthylene group) bonded to L2 is the same as the bonding position (No. 1′ in the formula (130Y)) of L2 (a naphthylene group) bonded to L1.
A group represented by the following formula (130-53) has an asymmetric structure because at least the bonding position (No. 1 in the formula (130Z)) of L1 (a naphthylene group) bonded to L2 is different from the bonding position (No. 2′ in the formula (130Z)) of L2 (a naphthylene group) bonded to L1.
Asymmetric Structure 3
Examples of -L1-L2- with the asymmetric structure 3 include groups represented by the formulae (13-7) to (13-48) described later in the second exemplary embodiment. The groups represented by the formulae (13-7) to (13-48) have an asymmetric structure because the structure of L1 is different from the structure of L2.
The asymmetric structure 4 is described below.
Asymmetric Structure 4
Examples of -L1-L2- with the asymmetric structure 4 include groups represented by one of the formulae (10-1), (20-1), and (30-1).
The asymmetric structure 4 is described with respect to the following formulae (100-1), (200-1), and (300-1), which are embodiments of the groups represented by the formulae (10-1), (20-1), and (30-1).
For example, a group represented by the following formula (100-1) has an asymmetric structure because the phenylene group of L1 having a substituent (a naphthylene group) is different from the unsubstituted phenylene group of L2, though the bonding position of *1 (No. 4 in the formula (130X)) is the same as the bonding position of *2 (No. 4′ in the formula (130X)).
A group represented by the following formula (200-1) has an asymmetric structure because the phenylene group of L2 having a substituent (a phenylene group) is different from the unsubstituted phenylene group of L1, though the bonding position of *1 (No. 5 in the formula (130X)) is the same as the bonding position of *2 (No. 3′ in the formula (130X)).
A group represented by the following formula (300-1) has an asymmetric structure because the bonding position of a phenylene group bonded to the phenylene group of L1 (No. 4 in the formula (130X)) is different from the bonding position of a phenylene group bonded to the phenylene group of L2 (No. 3 in the formula (130X)), though the bonding position of *1 (No. 6 in the formula (130X)) is the same as the bonding position of *2 (No. 6′ in the formula (130X)), and both the phenylene group of L1 and the phenylene group of L2 have the same substituent (the phenylene group).
In the compound according to the first exemplary embodiment, a compound represented by the formula (12X) is preferably a compound represented by the following formula (120).
In the compound according to the first exemplary embodiment, a compound represented by the following formula (120) represents the same as the compound according to the second exemplary embodiment.
In the formula (120), a substituted or unsubstituted 1-pyrenyl group with R102 to R110, a substituted or unsubstituted 1-pyrenyl group with R111 to R119, and L1 and L2 represent the same as Py1, Py2, L1, and L2, respectively, in the formula (12X).
In the formula (120), L1, L2, and R102 to R119 represent the same as L1, L2, and R102 to R119, respectively, in the compound according to the second exemplary embodiment, and the same applies to preferred ranges.
In the formula (120), R11 to R15, R21 to R27, and R31 to R37 in the formulae (11) to (13) representing L1 represent the same as R11 to R15, R21 to R27, and R31 to R37, respectively, in the compound according to the second exemplary embodiment, and the same applies to preferred ranges.
In the formula (120), R11A to R15A, R21A to R27A, and R31A to R37A in the formulae (11A) to (13A) representing L2 represent the same as R11A to R15A, R21A to R27A, and R31A to R37A, respectively, in the compound according to the second exemplary embodiment, and the same applies to preferred ranges.
In the compound according to the first exemplary embodiment, a compound represented by the formula (12X) is preferably a compound represented by the following formula (1), (2), or (3).
In the formulae (1) to (3), a substituted or unsubstituted 1-pyrenyl group with R211 to R219 represents the same as the substituent E of the substituted 1-pyrenyl group in the formula (12X), and a substituted or unsubstituted 1-pyrenyl group with R111 to R119 represents the same as the substituent E of the substituted 1-pyrenyl group in the formula (12X),
In the formulae (1) to (3), R111 to R119, R211 to R219, R11 to R14, R21 to R24, R31 to R34, R41 to R44, R51 to R54, and R61 to R64 represent the same as R111 to R119, R211 to R219, R11 to R14, R21 to R24, R31 to R34, R41 to R44, R51 to R54, and R61 to R64, respectively, in the compound according to the third exemplary embodiment, and the same applies to preferred ranges.
In the formula (2), preferably, R31 is different from R41, R32 is different from R42, R33 is different from R43, or R34 is different from R44. In the formula (3), R51 is different from R61, R52 is different from R62, R53 is different from R63, or R54 is different from R64.
The compound according to the first exemplary embodiment (a compound represented by the formula (12X)) can be produced by a known method. The compound according to the first exemplary embodiment can also be produced in accordance with a known method by using a known alternative reaction and raw materials suitable for the target compound.
Specific examples of the compound according to the first exemplary embodiment (a compound represented by the formula (12X)) are described in the specific examples of the compound according to the second exemplary embodiment (a compound represented by the formula (120)) or in the specific examples of the compound according to the third exemplary embodiment (a compound represented by the formula (1), (2), or (3)).
The compound according to the second exemplary embodiment is a compound represented by the following formula (120).
A compound represented by the following formula (120) is one example of the first compound (a compound represented by the formula (1A)).
A compound represented by the following formula (120) is a compound in which R101 in the formula (1A) is bonded to the formula (11) via a single bond.
A compound represented by the following formula (120) is one example of the compound according to the first exemplary embodiment (a compound represented by the formula (12X)).
The compound according to the second exemplary embodiment has an asymmetric structure as a whole because -L1-L2- in the following formula (120) has an asymmetric structure (one of the asymmetric structures 1 to 3).
In the formula (120):
In the formulae (11) to (13) and (11A) to (13A):
In the compound according to the second exemplary embodiment, -L1-L2- preferably represents a group represented by one of the following formulae (13-1) to (13-69).
In the formulae (13-1) to (13-69), R11 to R15, R21 to R27, R31 to R37, R11A to R15A, R21A to R27A, and R31A to R37A represent the same as R11 to R15, R21 to R27, R31 to R37, R11A to R15A, R21A to R27A, and R31A to R37A, respectively, in the formulae (11) to (13) and (11A) to (13A), *1 in the formulae (13-1) to (13-69) represents the position of bonding to *a in the formula (120), and *2 represents the position of bonding to *b in the formula (120).
In the compound according to the second exemplary embodiment, a compound represented by the formula (120) is preferably represented by one of the following formulae (121) to (131).
In the formulae (121) to (131),
In the compound according to the second exemplary embodiment, R11 to R15, R21 to R27, R31 to R37, R11A to R15A, R21A to R27A, R31A to R37A, and R102 to R119 preferably each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 30 carbon atoms, a group represented by —Si(Rx)(Ry)(Rz), a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. Rx, Ry, and Rz in the —Si(Rx)(Ry)(Rz) preferably each independently represent an unsubstituted alkyl group having 1 to 30 carbon atoms or an unsubstituted aryl group having 6 to 30 ring carbon atoms.
In the compound according to the second exemplary embodiment, R11 to R15, R21 to R27, R31 to R37, R11A to R15A, R21A to R27A, R31A to R37A, and R102 to R119 more preferably each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 18 carbon atoms, a group represented by —Si(Rx)(Ry)(Rz), a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms. Rx, Ry, and Rz in the —Si(Rx)(Ry)(Rz) more preferably each independently represent an unsubstituted alkyl group having 1 to 18 carbon atoms or an unsubstituted aryl group having 6 to 18 ring carbon atoms.
In the compound according to the second exemplary embodiment, R11 to R15, R21 to R27, R31 to R37, R11A to R15A, R21A to R27A, R31A to R37A, and R102 to R119 preferably each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9′-spirobifluorenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted pyrimidinyl group, a substituted or unsubstituted triazinyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted isoquinolyl group, a substituted or unsubstituted quinazolinyl group, a substituted or unsubstituted benzimidazolyl group, a substituted or unsubstituted phenanthrolinyl group, a substituted or unsubstituted 1-carbazolyl group, a substituted or unsubstituted 2-carbazolyl group, a substituted or unsubstituted 3-carbazolyl group, a substituted or unsubstituted 4-carbazolyl group, a substituted or unsubstituted 9-carbazolyl group, a substituted or unsubstituted benzocarbazolyl group, a substituted or unsubstituted azacarbazolyl group, a substituted or unsubstituted diazacarbazolyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted azadibenzofuranyl group, a substituted or unsubstituted diazadibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted naphthobenzothiophenyl group, a substituted or unsubstituted azadibenzothiophenyl group, or a substituted or unsubstituted diazadibenzothiophenyl group.
In the compound according to the second exemplary embodiment, R11 to R15, R21 to R27, R31 to R37, R11A to R15A, R21A to R27A, and R31A to R37A, and R102 to R119 preferably each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, or a substituted or unsubstituted 9,9-diphenylfluorenyl group.
In the compound according to the second exemplary embodiment, R11 to R15, R21 to R27, R31 to R37, R11A to R15A, R21A to R27A, and R31A to R37A, and R102 to R119 more preferably each independently represent a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, an unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, an unsubstituted dibenzofuranyl group, an unsubstituted dibenzothiophenyl group, an unsubstituted 9,9-dimethylfluorenyl group, or an unsubstituted 9,9-diphenylfluorenyl group.
In the compound according to the second exemplary embodiment, R11 to R15, R21 to R27, R31 to R37, R11A to R15A, R21A to R27A, and R31A to R37A preferably each represent a hydrogen atom.
In the compound according to the second exemplary embodiment, R102 to R119 preferably each represent a hydrogen atom.
In the compound according to the second exemplary embodiment, a substituent for “substituted or unsubstituted” in R11 to R15, R21 to R27, R31 to R37, R11A to R15A, R21A to R27A, R31A to R37A, and R102 to R119 is preferably each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, or a substituted or unsubstituted 9,9-diphenylfluorenyl group.
In the compound according to the second exemplary embodiment, a substituent for “substituted or unsubstituted” in R11 to R15, R21 to R27, R31 to R37, R11A to R15A, R21A to R27A, R31A to R37A, and R102 to R119 is more preferably each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 18 carbon atoms, an unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, an unsubstituted dibenzofuranyl group, an unsubstituted dibenzothiophenyl group, an unsubstituted 9,9-dimethylfluorenyl group, or an unsubstituted 9,9-diphenylfluorenyl group.
The compound according to the second exemplary embodiment in the emitting layer can improve luminous efficiency.
The compound according to the second exemplary embodiment (a compound represented by the formula (120)) can be produced by a known method. Furthermore, the compound according to the second exemplary embodiment can also be produced in accordance with a known method by using a known alternative reaction and raw materials suitable for the target compound.
Specific examples of the compound according to the second exemplary embodiment (a compound represented by the formula (120)) include the following compounds. However, the invention is not limited to these specific examples.
The compound according to the third exemplary embodiment is a compound represented by the following formula (1), (2), or (3).
The compound according to the third exemplary embodiment (the compound represented by the following formula (1), (2), or (3)) is an embodiment of the first compound (the compound that has at least one group represented by the formula (11) and is represented by the formula (1A)).
The compound according to the third exemplary embodiment is a compound in which R101 in the formula (1A) of the first compound is bonded to the formula (11) via a single bond.
A compound represented by the following formula (1), (2), or (3) is one example of the compound according to the first exemplary embodiment (a compound represented by the formula (12X)).
The compound according to the third exemplary embodiment, in which the linker linking two 1-pyrenyl groups in the following formula (1), (2), or (3) has an asymmetric structure (the asymmetric structure 4), has an asymmetric structure as a whole.
In the formulae (1) to (3),
In the formula (1):
In the formulae (2) to (3),
In a compound represented by the formula (1), a combination of R11 and R13 and a combination of R21 and R23 are different combinations, or a combination of R12 and R14 and a combination of R22 and R24 are different combinations.
In a compound represented by the formula (2), a combination of R31 and R41 is different from at least one combination of a combination of R32 and R42, a combination of R33 and R43, or a combination of R34 and R44.
In a compound represented by the formula (3), a combination of R51 and R61 is different from at least one combination of a combination of R52 and R62, a combination of R53 and R63, or a combination of R54 and R64.
In the formula (4):
In the formulae (1) to (3), a substituent for “substituted or unsubstituted” in R11 to R14, R21 to R24, R31 to R34, R41 to R44, R51 to R54, R61 to R64, R111 to R119, R211 to R219, and R311 to R319 is each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9′-spirobifluorenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, or a substituted or unsubstituted 9,9-diphenylfluorenyl group.
In the formula (1), the phenylene group with R11 to R14 corresponds to L1 in the formula (12X) of the first exemplary embodiment, and the phenylene group with R21 to R24 corresponds to L2 in the formula (12X) of the first exemplary embodiment.
In the formula (1), therefore, that “the linker linking two 1-pyrenyl groups has an asymmetric structure” refers to the asymmetric structure 4 in which the bonding position of the phenylene group (the phenylene group with R11 to R14) of L1 and the bonding position of the phenylene group (the phenylene group with R21 to R34) of L2 are para positions and are mutually the same, but the structure of L1 (the phenylene group with R11 to R14) and the structure of L2 (the phenylene group with R21 to R34) are mutually different including substituents.
In the formula (1), one embodiment in which the linker linking two 1-pyrenyl groups has an asymmetric structure is exemplified by an embodiment in which “a combination of R11 and R13 and a combination of R21 and R23 are different combinations, or a combination of R12 and R14 and a combination of R22 and R24 are different combinations”.
In the formula (1), “a combination of R11 and R13 and a combination of R21 and R23 are different combinations” is described below as an example. The following formulae (1a), (1b), and (1c) each represent a partial structure of the formula (1).
In the formulae (1a), (1b), and (1c):
For example, when R11 represents “A” and R13 represents “B”, that a combination of R11 and R13 and a combination of R21 and R23 are the same combination refers to that R21 represents “A” and R23 represents “B” (the formula (1a)), or R21 represents “B” and R23 represents “A” (the formula (1b)).
However, “A” is different from “B”.
When both R11 and R13 represent “A”, that a combination of R11 and R13 and a combination of R21 and R23 are the same combination refers to that both R21 and R23 represent “A” (the formula (1c)).
Thus, when a combination of R11 and R13 and a combination of R21 and R23 are different combinations, for example, R11 represents “A”, and R13 represents “B”, and both R21 and R23 represent “A”, or both R21 and R23 represent “B”, or at least one of R21 or R23 represents “C” that is different from “A” and “B”, or alternatively, both R11 and R13 represent “A”, and at least one of R21 or R23 represents “B”, or at least one of R21 or R23 represents “C” that is different from “A”.
The same applies to that “a combination of R12 and R14 and a combination of R22 and R24 are different combinations” in the formula (1).
In the formula (2), the phenylene group with R31 to R34 corresponds to L1 in the formula (12X) of the first exemplary embodiment, and the phenylene group with R41 to R44 corresponds to L2 in the formula (12X) of the first exemplary embodiment.
In the formula (2), therefore, that “the linker linking two 1-pyrenyl groups has an asymmetric structure” refers to the asymmetric structure 4 in which the bonding position of the phenylene group (the phenylene group with R31 to R34) of L1 and the bonding position of the phenylene group (the phenylene group with R41 to R44) of L2 are meta positions and are mutually the same, but the structure of L1 (the phenylene group with R31 to R34) and the structure of L2 (the phenylene group with R41 to R44) are mutually different including substituents.
More specifically, that “the linker linking two 1-pyrenyl groups has an asymmetric structure” means that R31 is different from R41, R32 is different from R42, R33 is different from R43, or R34 is different from R44.
In the formula (2), one embodiment in which the linker linking two 1-pyrenyl groups has an asymmetric structure is exemplified by an embodiment in which “a combination of R31 and R41 is different from at least one combination of a combination of R32 and R42, a combination of R33 and R43, or a combination of R34 and R44”.
“A combination of R31 and R41 is different from at least one combination of a combination of R32 and R42, a combination of R33 and R43, or a combination of R34 and R44” in the formula (2) is described below with respect to an example in which “a combination of R31 and R41 is different from a combination of R32 and R42”. The following formulae (2a), (2b), and (2c) represent a partial structure of the formula (2).
In the formulae (2a), (2b), and (2c), R33, R34, R43, and R44 represent the same as R33, R34, R43, and R44, respectively, in the formula (2).
For example, when R31 represents “A”, and R41 represents “B”, that a combination of R31 and R41 and a combination of R32 and R42 are the same combination refers to that R32 represents “A”, and R42 represents “B” (the formula (2a)), or R32 represents “B”, and R42 represents “A” (the formula (2b).
However, “A” is different from “B”.
When both R31 and R41 represent “A”, that a combination of R31 and R41 and a combination of R32 and R42 are the same combination refers to that both R32 and R42 represent “A” (the formula (2c)).
More specifically, when a combination of R31 and R41 and a combination of R32 and R42 are different combinations, for example, R31 represents “A”, R41 represents “B”, and both R32 and R42 represent “A”, or both R32 and R42 represent “B”, or at least one of R32 or R42 represents “C” that is different from “A” and “B”, or alternatively, both R31 and R41 represent “A”, and at least one of R32 or R42 represents “B”, or at least one of R32 or R42 represents “C” that is different from “A”.
The same applies to “a combination of R31 and R41 and a combination of R33 and R43 are different combinations” and “a combination of R31 and R41 and a combination of R34 and R44 are different combinations” in the formula (2).
In the formula (3), the phenylene group with R51 to R54 corresponds to L1 in the formula (12X) of the first exemplary embodiment, and the phenylene group with R61 to R64 corresponds to L2 in the formula (12X) of the first exemplary embodiment.
In the formula (3), therefore, that “the linker linking two 1-pyrenyl groups has an asymmetric structure” refers to the asymmetric structure 4 in which the bonding position of the phenylene group (the phenylene group with R51 to R54) of L1 and the bonding position of the phenylene group (the phenylene group with R61 to R64) of L2 are ortho positions and are mutually the same, but the structure of L1 (the phenylene group with R51 to R54) and the structure of L2 (the phenylene group with R61 to R64) are mutually different including substituents.
More specifically, that “the linker linking two 1-pyrenyl groups has an asymmetric structure” means that R51 is different from R61, R52 is different from R62, R53 is different from R63, or R54 is different from R64.
In the formula (2), one embodiment in which the linker linking two 1-pyrenyl groups has an asymmetric structure is exemplified by an embodiment in which “a combination of R51 and R61 is different from at least one combination of a combination of R52 and R62, a combination of R53 and R63, or a combination of R54 and R64”.
“A combination of R51 and R61 is different from at least one combination of a combination of R52 and R62, a combination of R53 and R63, or a combination of R54 and R64” in the formula (3) is described below with respect to an example in which “a combination of R51 and R61 is different from a combination of R52 and R62”. The following formulae (3a), (3b), and (3c) represent a partial structure of the formula (3).
In the formulae (3a), (3b), and (3c),
For example, when R51 represents “A” and R61 represents “B”, that a combination of R51 and R61 and a combination of R52 and R62 are the same combination refers to that R52 represents “A” and R62 represents “B” (the formula (3a)), or R52 represents “B” and R62 represents “A” (the formula (3b)).
However, “A” is different from “B”.
When both R51 and R61 represent “A”, that a combination of R51 and R61 and a combination of R52 and R62 are the same combination refers to that both R52 and R62 represent “A” (the formula (3c)).
Thus, when a combination of R51 and R61 and a combination of R52 and R62 are different combinations refers to, for example, when R51 represents “A” and R61 represents “B”, both R52 and R62 represent “A”, or both R52 and R62 represent “B”, or at least one of R52 or R62 represents “C” that is different from “A” and “B”, when both R51 and R61 represent “A” and at least one of R52 or R62 represents “B”, or when at least one of R52 or R62 represents “C” that is different from “A”.
The same applies to “a combination of R51 and R61 and a combination of R53 and R63 are different combinations” and “a combination of R51 and R61 and a combination of R54 and R64 are different combinations” in the formula (3).
In the compound according to the third exemplary embodiment, R111 to R119 and R211 to R219 preferably each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted cycloalkyl group having 1 to 18 carbon atoms, a group represented by —Si(Rx)(Ry)(Rz), a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms. Rx, Ry, and Rz in the —Si(Rx)(Ry)(Rz) preferably each independently represent an unsubstituted alkyl group having 1 to 18 carbon atoms or an unsubstituted aryl group having 6 to 18 ring carbon atoms.
In the compound according to the third exemplary embodiment, R111 to R119 and R211 to R219 preferably each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 18 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, or a substituted or unsubstituted 9,9-diphenylfluorenyl group.
In the compound according to the third exemplary embodiment, R111 to R119 and R211 to R219 preferably represent a hydrogen atom.
In the compound according to the third exemplary embodiment, preferably, at least one combination of a combination of R11 and R12, a combination of R13 and R14, a combination of R21 and R22, or a combination of R23 and R24 are not mutually bonded, and at least one combination of adjacent two or more of R31 to R33, R41 to R43, R51 to R54, and R61 to R64 are not mutually bonded.
The compound according to the third exemplary embodiment is preferably represented by the following formula (1-1), (2-1), or (3-1).
In the formulae (1-1), (2-1), and (3-1), R11 to R14, R21 to R24, R31 to R34, R41 to R44, R51 to R54, and R61 to R64 represent the same as R11 to R14, R21 to R24, R31 to R34, R41 to R44, R51 to R54, and R61 to R64, respectively, in the formulae (1) to (3).
In the compound according to the third exemplary embodiment, R11 to R14, R21 to R24, R31 to R34, R41 to R44, R51 to R54, and R61 to R64 preferably each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9′-spirobifluorenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group, and R12, R14, R22, and R24 are preferably not a substituted or unsubstituted phenyl group.
In the compound according to the third exemplary embodiment, R11 to R14, R21 to R24, R31 to R34, R41 to R44, R51 to R54, and R61 to R64 more preferably each independently represent a hydrogen atom, an unsubstituted alkyl group having 1 to 8 carbon atoms, an unsubstituted phenyl group, an unsubstituted biphenyl group, an unsubstituted naphthyl group, an unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, an unsubstituted 9,9′-spirobifluorenyl group, an unsubstituted 9,9-dimethylfluorenyl group, an unsubstituted 9,9-diphenylfluorenyl group, an unsubstituted dibenzofuranyl group, or an unsubstituted dibenzothiophenyl group, and R12, R14, R22, and R24 are more preferably not a substituted or unsubstituted phenyl group.
In the compound according to the third exemplary embodiment, at least one combination of a combination of R11 and R12, a combination of R13 and R14, a combination of R21 and R22, or a combination of R23 and R24 is preferably mutually bonded to form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring, and at least one combination of adjacent two or more of R31 to R33, R41 to R43, R51 to R54, and R61 to R64 are preferably mutually bonded to form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring.
In the compound according to the third exemplary embodiment, a combination of R11 and R12, a combination of R13 and R14, a combination of R21 and R22, and a combination of R23 and R24 are also preferably not bonded mutually.
More specifically, in the compound according to the third exemplary embodiment, also preferably, a combination of R11 and R12 are not mutually bonded, a combination of R13 and R14 are not mutually bonded, a combination of R21 and R22 are not mutually bonded, and a combination of R23 and R24 are not mutually bonded.
In the compound according to the third exemplary embodiment, a combination of adjacent two or more of R31 to R33, R41 to R43, R51 to R54, and R61 to R64 are also preferably not bonded to each other.
The compound according to the third exemplary embodiment is preferably represented by one of the following formulae (1-2), (2-2) to (2-3), and (3-2) to (3-4).
In the formulae (1-2), (2-2) to (2-3), and (3-2) to (3-4), R13 to R14, R21 to R22, R31, R33, R34, R41, R43, R44, R51 to R54, and R61 to R64 represent the same as R13 to R14, R21 to R22, R31, R33, R34, R41, R43, R44, R51 to R54, and R61 to R64, respectively, in the formulae (1) to (3), and R301 to R308 each independently represent the same as R11 to R14, R21 to R24, R31 to R34, R41 to R44, R51 to R54, and R61 to R64 in the formulae (1) to (3).
In the formulae (1-2), (2-2) to (2-3), and (3-2) to (3-4):
In the formulae (1-2), (2-2) to (2-3), and (3-2) to (3-4):
In the compound according to the third exemplary embodiment, a substituent for “substituted or unsubstituted” in R11 to R14, R21 to R24, R31 to R34, R41 to R44, R51 to R54, R61 to R64, R111 to R119, R211 to R219, and R301 to R308 is preferably each independently a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, or a substituted or unsubstituted 9,9-diphenylfluorenyl group.
In the compound according to the third exemplary embodiment, a substituent for “substituted or unsubstituted” in R11 to R14, R21 to R24, R31 to R34, R41 to R44, R51 to R54, R61 to R64, R111 to R119, R211 to R219, and R301 to R308 is preferably each independently an unsubstituted alkyl group having 1 to 8 carbon atoms, an unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, an unsubstituted dibenzofuranyl group, an unsubstituted dibenzothiophenyl group, an unsubstituted 9,9-dimethylfluorenyl group, or an unsubstituted 9,9-diphenylfluorenyl group.
The compound according to the third exemplary embodiment in an emitting layer can improve luminous efficiency.
The compound according to the third exemplary embodiment (a compound represented by the formula (1), (2), or (3)) can be produced by a known method. Furthermore, the compound according to the third exemplary embodiment can also be produced in accordance with a known method by using a known alternative reaction and raw materials suitable for the target compound.
Specific examples of the compound according to the third exemplary embodiment (a compound represented by the formula (1), (2), or (3)) include the following compounds. However, the invention is not limited to these specific examples.
An organic-EL-device material according to a fourth exemplary embodiment contains the compound according to the first exemplary embodiment (a compound represented by the formula (12X)), the compound according to the second exemplary embodiment (a compound represented by the formula (120)), or the compound according to the third exemplary embodiment (at least one of compounds represented by one of the formulae (1) to (3)).
The fourth exemplary embodiment provides an organic-EL-device material that can improve luminous efficiency.
The organic-EL-device material according to the fourth exemplary embodiment may further contain another compound. In the organic-EL-device material according to the fourth exemplary embodiment containing another compound, the other compound may be solid or liquid.
The structure of an organic EL device according to a fifth exemplary embodiment is described below.
The organic EL device according to the fifth exemplary embodiment includes an anode, a cathode, and an emitting layer between the anode and the cathode.
The emitting layer contains the compound according to the first exemplary embodiment (a compound represented by the formula (12X)), the compound according to the second exemplary embodiment (a compound represented by the formula (120)), or the compound according to the third exemplary embodiment (at least one of compounds represented by one of the formulae (1) to (3)).
The emitting layer preferably contains the compound according to the first exemplary embodiment, the compound according to the second exemplary embodiment, or the compound according to the third exemplary embodiment as a host material.
Herein, the “host material” is a material constituting “50% or more by mass of the layer”, for example. Thus, for example, the emitting layer contains the compound according to the first exemplary embodiment, the compound according to the second exemplary embodiment, or the compound according to the third exemplary embodiment, which constitutes 50% or more by mass of the total mass of the emitting layer.
Emission Wavelength of Organic EL Device
The organic EL device according to the fifth exemplary embodiment preferably emits light with a main peak wavelength in the range of 430 to 480 nm when driven.
The main peak wavelength of light emitted from an organic EL device driven is measured as described below. While a voltage is applied to an organic EL device at an electric current density of 10 mA/cm2, a spectral radiance spectrum is measured with a spectral radiance meter CS-2000 (manufactured by Konica Minolta, Inc. In a spectral radiance spectrum thus measured, the peak wavelength of an emission spectrum with a maximum luminous intensity is measured as a main peak wavelength (unit: nm).
The organic EL device according to the fifth exemplary embodiment may have at least one organic layer in addition to the emitting layer. The organic layer may be at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, an electron injecting layer, an electron transporting layer, a hole blocking layer, and an electron blocking layer. The emitting layer may be composed of two or more layers.
In the organic EL device according to the fifth exemplary embodiment, the organic layer may consist of the emitting layer or may further have at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, an electron injecting layer, an electron transporting layer, a hole blocking layer, an electron blocking layer, and the like.
The organic EL device according to the fifth exemplary embodiment preferably has a hole transporting layer between the anode and the emitting layer.
The organic EL device according to the fifth exemplary embodiment preferably has an electron transporting layer between the anode and the emitting layer.
An organic EL device 1 includes a light-transmitting substrate 2, an anode 3, a cathode 4, and an organic layer 10 between the anode 3 and the cathode 4. The organic layer 10 is composed of a hole injecting layer 6, a hole transporting layer 7, an emitting layer 5, an electron transporting layer 8, and an electron injecting layer 9 layered in this order on the side of the anode 3.
Fluorescent Compound
In the organic EL device 1 according to the fifth exemplary embodiment, the emitting layer 5 preferably further contains a fluorescent compound (hereinafter also referred to as a “compound M1”).
In the organic EL device 1 according to the fifth exemplary embodiment, the fluorescent compound (the compound M1) is preferably at least one compound selected from the group consisting of the compounds represented by the following formula (100), the compounds represented by the following formula (3), the compounds represented by the following formula (4), the compounds represented by the following formula (5), the compounds represented by the following formula (6), the compounds represented by the following formula (7), the compounds represented by the following formula (8), the compounds represented by the following formula (9), and the compounds represented by the following formula (10).
Compound Represented by Formula (100)
A compound represented by the formula (100) is described below.
In the formula (100):
A specific example in which “at least one combination of a combination of adjacent two or more of R11 to R16, a combination of adjacent two or more of R17 to R20, a combination of adjacent two or more of Ra1 to Ra5, and a combination of adjacent two or more of Ra6 to Ra10” are mutually bonded to form a substituted or unsubstituted monocyclic ring or fused ring having 3 to 30 ring atoms is described below.
In a specific example in which a combination of adjacent two or more are mutually bonded to form a fused ring, in the case of R17 to R20 in the formula (100), a compound represented by the following formula (10A) is one example. In the compound represented by the following formula (10A), three adjacent R11, R19, and R20 are mutually bonded to form a fused ring.
In the formula (10A), Ra1 to Ra10 and R11 to R17 represent the same as Ra1 to Ra10 and R11 to R17, respectively, in the formula (100).
In a specific example in which a combination of adjacent two or more are mutually bonded to form a monocyclic ring, for R11 to R16 in the formula (100), a compound represented by the following formula (10B) is one example. In the compound represented by the following formula (10B), a combination of R12 and R13 and a combination of R14 and R15 are independently bonded to each other to form two monocyclic rings.
In the formula (10B), Ra1 to Ra10, R11, and R16 to R20 represent the same as Ra1 to Ra10, R11, and R16 to R20, respectively, in the formula (100).
In an exemplary embodiment, a compound represented by the formula (100) is a compound represented by the following formula (10-1).
In the formula (10-1):
In the formula (10-1), n10 preferably represents 0, 1, or 2.
In the formula (10-1), L100 preferably represents a divalent group derived by removing one hydrogen atom from a group selected from the group consisting of a single bond, a substituted or unsubstituted phenyl group, substituted or unsubstituted biphenyl group, substituted or unsubstituted terphenyl group, substituted or unsubstituted naphthyl group, substituted or unsubstituted anthryl group, substituted or unsubstituted phenanthryl group, substituted or unsubstituted fluorenyl group, substituted or unsubstituted 9,9′-spirobifluorenyl group, substituted or unsubstituted 9,9-dimethylfluorenyl group, substituted or unsubstituted 9,9-diphenylfluorenyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted naphthobenzofuranyl group, substituted or unsubstituted dibenzothiophenyl group, and substituted or unsubstituted naphthobenzothiophenyl group.
Ar100 in the formula (10-1) preferably represents a cyano group, a substituted silyl group, a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthryl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted 9,9′-spirobifluorenyl group, a substituted or unsubstituted 9,9-dimethylfluorenyl group, a substituted or unsubstituted 9,9-diphenylfluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted naphthobenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted naphthobenzothiophenyl group.
In the formula (10-1), at least one combination of a combination of adjacent two or more of R11 to R12, R14 to R16, and R17 to R20, a combination of adjacent two or more of Ra1 to Ra5, and a combination of adjacent two or more of Ra6 to Ra10 are mutually bonded to form a substituted or unsubstituted monocyclic ring having 3 to 30 ring atoms or form a substituted or unsubstituted fused ring having 3 to 30 ring atoms, or are not mutually bonded.
In an exemplary embodiment, R12 and R13 in the formula (100) are mutually bonded to form a substituted or unsubstituted monocyclic ring having 3 to 30 ring atoms or form a substituted or unsubstituted fused ring having 3 to 30 ring atoms.
In an exemplary embodiment, a compound represented by the formula (100) is a compound represented by the following formula (10-2).
In the formula (10-2),
When a plurality of R901 are present, the plurality of R901 are mutually the same or different. When a plurality of R902 are present, the plurality of R902 are mutually the same or different. When a plurality of R903 are present, the plurality of R903 are mutually the same or different. When a plurality of R904 are present, the plurality of R904 are mutually the same or different. When a plurality of R905 are present, the plurality of R905 are mutually the same or different. When a plurality of R906 are present, the plurality of R906 are mutually the same or different. When a plurality of R907 are present, the plurality of R907 are mutually the same or different.
In the formula (10-2), at least one combination of a combination of adjacent two or more of R14 to R16 and R17 to R20, a combination of adjacent two or more of Ra1 to Ra5, a combination of adjacent two or more of Ra6 to Ra10, a combination of adjacent two or more of Rc3 to Rc8, and a combination of Rc1 and Rc2 are mutually bonded to form a substituted or unsubstituted monocyclic ring having 3 to 30 ring atoms or form a substituted or unsubstituted fused ring having 3 to 30 ring atoms, or are not mutually bonded.
In an exemplary embodiment, two or more of R1, to R20 in the formula (100) are mutually bonded to form a substituted or unsubstituted monocyclic ring having 3 to 30 ring atoms or form a substituted or unsubstituted fused ring having 3 to 30 ring atoms.
In an exemplary embodiment, a compound represented by the formula (100) is a compound represented by the following formula (10-3).
In the formula (10-3), R11 to R17, Ra1 to Ra10, and Rd1 to Rd7 each independently represent the same as R11 to R20 in the formula (100).
In the formula (10-3), at least one combination of a combination of adjacent two or more of R11 to R16, a combination of adjacent two or more of R17 and Rd1 to Rd7, a combination of adjacent two or more of Ra1 to Ra5, and a combination of adjacent two or more of Ra6 to Ra10 are mutually bonded to form a substituted or unsubstituted monocyclic ring having 3 to 30 ring atoms or form a substituted or unsubstituted fused ring having 3 to 30 ring atoms, or are not mutually bonded.
In an exemplary embodiment, R11 to R20, Ra1 to Ra5, Ra6 to Ra10, Rc1 to Rc8, and Rd1 to Rd7 that are not involved in ring formation in the formulae (100) and (10-1) to (10-3) each independently represent a hydrogen atom, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
Specific examples of a compound represented by the formula (100) include the following compounds.
(Compound Represented by Formula (3))
A compound represented by the formula (3) is described below.
In the formula (3),
In the formula (31),
In the fluorescent compound (the compound M1), R901, R902, R903, R904, R905, R906, and R907 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,
In the formula (3), two of R301 to R310 preferably represent a group represented by the formula (31).
In an exemplary embodiment, a compound represented by the formula (3) is a compound represented by the following formula (33).
In the formula (33),
In the formula (31), L301 preferably represents a single bond, and L302 and L303 preferably represent a single bond.
In an exemplary embodiment, a compound represented by the formula (3) is represented by the following formula (34) or (35).
In the formula (34),
In the formula (35),
In the formula (31), preferably, at least one of Ar301 or Ar302 represents a group represented by the following formula (36).
In the formulae (33) to (35), preferably, at least one of Ar312 or Ar313 represents a group represented by the following formula (36).
In the formulae (33) to (35), preferably, at least one of Ar315 or Ar316 represents a group represented by the following formula (36).
In the formula (36),
At least one of R321 to R327 preferably represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In the formula (31), Ar301 preferably represents a group represented by the formula (36), and Ar302 preferably represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In the formulae (33) to (35), Ar312 preferably represents a group represented by the formula (36), and Ar313 preferably represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In the formulae (33) to (35), Ar315 preferably represents a group represented by the formula (36), Ar316 preferably represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In an exemplary embodiment, a compound represented by the formula (3) is represented by the following formula (37).
In the formula (37),
Specific examples of a compound represented by the formula (3) include the following compounds.
Compound Represented by Formula (4)
A compound represented by the formula (4) is described below.
In the formula (4),
The “aromatic hydrocarbon rings” of the A1 ring and the A2 ring have the same structure as compounds in which a hydrogen atom is introduced into the “aryl group” described above.
The “aromatic hydrocarbon rings” of the A1 ring and the A2 ring have two carbon atoms on the central fused bicyclic structure of the formula (4) as ring atoms.
Specific examples of the “substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms” include compounds in which a hydrogen atom is introduced into the “aryl group” described in the specific example group G1.
The “heterocycles” of the A1 ring and the A2 ring have the same structure as compounds in which a hydrogen atom is introduced into the “heterocyclic group” described above.
The “heterocycles” of the A1 ring and the A2 ring have two carbon atoms on the central fused two-ring structure of the formula (4) as ring atoms.
Specific examples of the “substituted or unsubstituted heterocycle having 5 to 50 ring atoms” include compounds in which a hydrogen atom is introduced into the “heterocyclic groups” described in the specific example group G2.
Rb is bonded to one of the carbon atoms forming the aromatic hydrocarbon ring of the A1 ring or to one of the atoms forming the heterocycle of the A1 ring.
Rc is bonded to one of the carbon atoms forming the aromatic hydrocarbon ring of the A2 ring or to one of the atoms forming the heterocycle of the A2 ring.
At least one of Ra, Rb, or Rc is preferably a group represented by the following formula (4a), and at least two of Ra, Rb, or Rc are more preferably groups represented by the following formula (4a).
[Formula 152]
*-L401-Ar401 (4a)
In the formula (4a),
In the formula (4b),
In an exemplary embodiment, a compound represented by the formula (4) is represented by the following formula (42).
In the formula (42),
At least one of R401 to R411 is preferably a group represented by the formula (4a), and at least two of Ra, Rb, or Rc are more preferably groups represented by the formula (4a).
R404 and R411 are preferably groups represented by the formula (4a).
In an exemplary embodiment, a compound represented by the formula (4) is a compound in which a structure represented by the formula (4-1) or the formula (4-2) described below is bonded to the A1 ring.
In an exemplary embodiment, a compound represented by the formula (42) is a compound in which a structure represented by the formula (4-1) or the formula (4-2) described below is bonded to the ring bonded to R404 to R407.
In an exemplary embodiment, a compound represented by the formula (4) is a compound represented by the following formula (41-3), (41-4), or (41-5).
In the formulae (41-3), (41-4), and (41-5),
In an exemplary embodiment, a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms of the A1 ring in the formula (41-5) is a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted fluorene ring.
In an exemplary embodiment, a substituted or unsubstituted heterocycle having 5 to 50 ring atoms of the A1 ring in the formula (41-5) is a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring, or a substituted or unsubstituted dibenzothiophene ring.
In an exemplary embodiment, a compound represented by the formula (4) or (42) is selected from the group consisting of the compounds represented by the following formulae (461) to (467).
In the formula (461), the formula (462), the formula (463), the formula (464), the formula (465), the formula (466), and the formula (467),
In an exemplary embodiment, at least one combination of adjacent two or more of R401 to R411 in a compound represented by the formula (42) are mutually bonded to form a substituted or unsubstituted monocyclic ring, or are mutually bonded to form a substituted or unsubstituted fused ring. This exemplary embodiment is described in detail below with respect to a compound represented by the following formula (45).
Compound Represented by Formula (45)
A compound represented by the formula (45) is described below.
In the formula (45),
In the formula (45), Rn and Rn+1 (n represents an integer selected from 461, 462, 464 to 466, and 468 to 470) are mutually bonded and, together with two ring carbon atoms bonded to Rn and Rn+1 form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring. The ring is preferably composed of atoms selected from the group consisting of a carbon atom, an oxygen atom, a sulfur atom, and a nitrogen atom, and the number of atoms in the ring preferably ranges from 3 to 7, more preferably 5 or 6.
The number of the ring structures in a compound represented by the formula (45) is two, three, or four, for example. The two or more ring structures may be present on the same benzene ring or different benzene rings on the parent skeleton of the formula (45). For example, for three ring structures, one ring structure may be present in each of the three benzene rings of the formula (45).
The ring structures in a compound represented by the formula (45) are structures represented by the following formulae (451) to (460), for example.
In the formulae (451) to (457),
In the formulae (458) to (460),
In the formula (45), at least one of R462, R464, R465, R470, or R471 (preferably at least one of R462, R465, or R470, more preferably R462) is preferably a group that does not form a ring structure.
It is preferable that (i) a substituent of a ring structure formed by Rn and Rn+1 having the substituent in the formula (45), (ii) R461 to R471 that do not form a ring structure in the formula (45), and (iii) R4501 to R4514 and R4515 to R4525 in the formulae (451) to (460) each independently represent a group selected from the group consisting of a hydrogen atom, substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, group represented by —N(R906)(R907), substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and group represented by the following formulae (461) to (464).
In the formulae (461) to (464),
In the fluorescent compound (the compound M1), R901 to R907 are as defined above.
In an exemplary embodiment, a compound represented by the formula (45) is represented by one of the following formulae (45-1) to (45-6).
In the formulae (45-1) to (45-6), rings d to i each independently represent a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring, and R461 to R471 represent the same as R461 to R471, respectively, in the formula (45).
In an exemplary embodiment, a compound represented by the formula (45) is represented by one of the following formulae (45-7) to (45-12).
In the formulae (45-7) to (45-12), rings d to f, k, and j each independently represent a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring, and R461 to R471 represent the same as R461 to R471, respectively, in the formula (45).
In an exemplary embodiment, a compound represented by the formula (45) is represented by one of the following formulae (45-13) to (45-21).
In the formulae (45-13) to (45-21), rings d to k each independently represent a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted fused ring, and R461 to R471 represent the same as R461 to R471, respectively, in the formula (45).
When the ring g or the ring h further has a substituent, the substituent is, for example, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a group represented by the formula (461), a group represented by the formula (463), or a group represented by the formula (464).
In an exemplary embodiment, a compound represented by the formula (45) is represented by one of the following formulae (45-22) to (45-25).
In the formulae (45-22) to (45-25),
In an exemplary embodiment, a compound represented by the formula (45) is represented by the following formula (45-26).
In the formula (45-26),
Specific examples of a compound represented by the formula (4) include the following compounds.
Compound Represented by Formula (5)
A compound represented by the formula (5) is described below. A compound represented by the formula (5) is a compound corresponding to a compound represented by the formula (41-3).
In the formula (5),
“A combination of adjacent two or more of R501 to R507 and R511 to R517” is a combination of R501 and R502, a combination of R502 and R503, a combination of R503 and R504, a combination of R505 and R506, a combination of R506 and R507, or a combination of R501, R502, and R503, for example.
In an exemplary embodiment, at least one, preferably two, of R501 to R507 or R511 to R517 is a group represented by —N(R906)(R907).
In an exemplary embodiment, R501 to R507 and R511 to R517 each independently represent a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In an exemplary embodiment, a compound represented by the formula (5) is a compound represented by the following formula (52).
In the formula (52),
In an exemplary embodiment, a compound represented by the formula (5) is a compound represented by the following formula (53).
In the formula (53), R551, R552, and R561 to R564 represent the same as R551, R552, and R561 to R564, respectively, in the formula (52).
In an exemplary embodiment, R561 to R564 in the formula (52) and the formula (53) each independently represent a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms (preferably a phenyl group).
In an exemplary embodiment, R521 and R522 in the formula (5) and R551 and R552 in the formula (52) and the formula (53) are hydrogen atoms.
In an exemplary embodiment, a substituent for “substituted or unsubstituted” in the formula (5), the formula (52), and the formula (53) is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
Specific examples of a compound represented by the formula (5) include the following compounds.
(In the formulae, Ph denotes a phenyl group.)
Compound Represented by Formula (6)
A compound represented by the formula (6) is described below.
In the formula (6),
The a ring, the b ring, and the c ring are rings (substituted or unsubstituted aromatic hydrocarbon rings having 6 to 50 ring carbon atoms or substituted or unsubstituted heterocycles having 5 to 50 ring atoms) fused to the central fused bicyclic structure of the formula (6) including a boron atom and two nitrogen atoms.
The “aromatic hydrocarbon rings” of the a ring, the b ring, and the c ring have the same structure as compounds in which a hydrogen atom is introduced into the “aryl group” described above.
The “aromatic hydrocarbon ring” of the a ring has three carbon atoms on the central fused bicyclic structure of the formula (6) as ring atoms.
The “aromatic hydrocarbon rings” of the b and c rings have two carbon atoms on the central fused bicyclic structure of the formula (6) as ring atoms.
Specific examples of the “substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms” include compounds in which a hydrogen atom is introduced into the “aryl group” described in the specific example group G1.
The “heterocycles” of the a ring, the b ring, and the c ring have the same structure as compounds in which a hydrogen atom is introduced into the “heterocyclic group” described above.
The “heterocycle” of the a ring has three carbon atoms on the central fused bicyclic structure of the formula (6) as ring atoms. The “heterocycles” of the b ring and the c ring have two carbon atoms on the central fused bicyclic structure of the formula (6) as ring atoms. Specific examples of the “substituted or unsubstituted heterocycle having 5 to 50 ring atoms” include compounds in which a hydrogen atom is introduced into the “heterocyclic group” described in the specific example group G2.
R601 and R602 may be each independently bonded to the a ring, the b ring, or the c ring to form a substituted or unsubstituted heterocycle. This heterocycle has the nitrogen atom on the central fused bicyclic structure of the formula (6). The heterocycle may have a heteroatom other than the nitrogen atom. The phrase “R601 and R602 are each independently bonded to the a ring, the b ring, or the c ring” more specifically means that an atom constituting the a ring, the b ring, or the c ring is bonded to an atom constituting R601 and R602. For example, R601 may be bonded to the a ring to form a fused bicyclic (or fused tricyclic or higher cyclic) nitrogen-containing heterocycle in which the ring with R601 is fused to the a ring. Specific examples of the nitrogen-containing heterocycle include compounds corresponding to fused bicyclic or higher cyclic heterocyclic group containing nitrogen of the specific example group G2.
The same applies to when R601 is bonded to the b ring, when R602 is bonded to the a ring, and when R602 is bonded to the c ring.
In an exemplary embodiment, the a ring, the b ring, and the c ring in the formula (6) are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms.
In an exemplary embodiment, the a ring, the b ring, and the c ring in the formula (6) are each independently a substituted or unsubstituted benzene ring or naphthalene ring.
In an exemplary embodiment, R601 and R602 in the formula (6) each independently represent a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In an exemplary embodiment, a compound represented by the formula (6) is a compound represented by the following formula (62).
In the formula (62),
For example, R601A may be bonded to R611 to form a fused bicyclic (or fused tricyclic or higher cyclic) nitrogen-containing heterocycle in which and the ring with R601A and R611 is fused to a benzene ring corresponding to the a ring. Specific examples of the nitrogen-containing heterocycle include compounds corresponding to fused bicyclic or higher cyclic heterocyclic groups containing nitrogen of the specific example group G2. The same applies to when R601A is bonded to R621, when R602A is bonded to R613, and when R602A is bonded to R614.
At least one combination of adjacent two or more of R611 to R621
For example, R611 and R612 may be mutually bonded to form a structure in which a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, or a benzothiophene ring is fused to the 6-membered ring bonded to R611 and R612. The fused ring thus formed is a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, or a dibenzothiophene ring.
In an exemplary embodiment, R611 to R621 that do not contribute to ring formation each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In an exemplary embodiment, R611 to R621 that do not contribute to ring formation each independently represent a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In an exemplary embodiment, R611 to R621 that do not contribute to ring formation each independently represent a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
In an exemplary embodiment, R611 to R621 that do not contribute to ring formation each independently represent a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, in which at least one of R611 to R621 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
In an exemplary embodiment, a compound represented by the formula (62) is a compound represented by the following formula (63).
In the formula (63),
In an exemplary embodiment, R631 to R651 that do not contribute to ring formation each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In an exemplary embodiment, R631 to R651 that do not contribute to ring formation each independently represent a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In an exemplary embodiment, R631 to R651 that do not contribute to ring formation each independently represent a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
In an exemplary embodiment, R631 to R651 that do not contribute to ring formation each independently represent a hydrogen atom, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and at least one of R631 to R651 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
In an exemplary embodiment, a compound represented by the formula (63) is a compound represented by the following formula (63A).
In the formula (63A),
In an exemplary embodiment, R661 to R665 each independently represent a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In an exemplary embodiment, R661 to R665 each independently represent a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
In an exemplary embodiment, a compound represented by the formula (63) is a compound represented by the following formula (63B).
In the formula (63B),
In an exemplary embodiment, a compound represented by the formula (63) is a compound represented by the following formula (63B′).
In the formula (63B′), R672 to R675 represent the same as R672 to R675, respectively, in the formula (63B).
In an exemplary embodiment, at least one of R671 to R675 represents a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —N(R906)(R907), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In an exemplary embodiment, R672 represents a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a group represented by —N(R906)(R907), or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and
In an exemplary embodiment, a compound represented by the formula (63) is a compound represented by the following formula (63C).
In the formula (63C),
R683 to R686 each independently represent a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In an exemplary embodiment, a compound represented by the formula (63) is a compound represented by the following formula (63C′).
In the formula (63C′), R683 to R686 represent the same as R683 to R686, respectively, in the formula (63C).
In an exemplary embodiment, R681 to R686 each independently represent a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In an exemplary embodiment, R681 to R686 each independently represent a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
A compound represented by the formula (6) can be produced by first bonding the a ring, the b ring, and the c ring to each other with a linking group (a group containing N—R601 and a group containing N—R602) to produce an intermediate (a first reaction) and then bonding the a ring, the b ring, and the c ring to each other with a linking group (a group containing a boron atom) to produce an end product (a second reaction). In the first reaction, an amination reaction, such as a Buchwald-Hartwig reaction, can be used. In the second reaction, a tandem hetero Friedel-Crafts reaction or the like can be used.
Specific examples of a compound represented by the formula (6) are described below. These are only examples, and a compound represented by the formula (6) is not limited to these specific examples.
Compound Represented by Formula (7)
A compound represented by the formula (7) is described below.
In the formula (7),
When a plurality of R701 are present, a plurality of adjacent R701 are mutually bonded to form a substituted or unsubstituted monocyclic ring, are mutually bonded to form a substituted or unsubstituted fused ring, or are not mutually bonded,
In the formula (7), each of the p ring, the q ring, the r ring, the s ring, and the t ring is fused to an adjacent ring by sharing two carbon atoms. The position and direction where the rings are fused are not particularly limited. The rings may be fused at any position and in any direction.
In an exemplary embodiment, in the r ring represented by the formula (72) or the formula (73), m1 is 0, or m2 is 0.
In an exemplary embodiment, a compound represented by the formula (7) is represented by one of the following formulae (71-1) to (71-6).
In the formulae (71-1) to (71-6), R701, X7, Ar701, Ar702, L701, m1, and m3 represent the same as R701, X7, Ar701, Ar702, L701, m1, and m3, respectively, in the formula (7).
In an exemplary embodiment, a compound represented by the formula (7) is represented by one of the following formulae (71-11) to (71-13).
In the formula (71-11) to the formula (71-13), R701, X7, Ar701, Ar702, L701, m1, m3, and m4 represent the same as R701, X7, Ar701, Ar702, L701, m1, m3, and m4, respectively, in the formula (7).
In an exemplary embodiment, a compound represented by the formula (7) is represented by one of the following formulae (71-21) to (71-25).
In the formula (71-21) to the formula (71-25), R701, X7, Ar701, Ar702, L701, m1, and m4 represent the same as R701, X7, Ar701, Ar702, L701, m1, and m4, respectively, in the formula (7).
In an exemplary embodiment, a compound represented by the formula (7) is represented by one of the following formulae (71-31) to (71-33).
In the formula (71-31) to the formula (71-33), R701, X7, Ar701, Ar702, L701, m2, to m4 represent the same as R701, X7, Ar701, Ar702, L701, m2, to m4, respectively, in the formula (7).
In an exemplary embodiment, Ar701 and Ar702 each independently represent a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In an exemplary embodiment, one of Ar701 and Ar702 represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and the other of Ar701 and Ar702 represents a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
Specific examples of a compound represented by the formula (7) include the following compounds.
Compound Represented by Formula (8)
A compound represented by the formula (8) is described below.
In the formula (8),
At least one of R801 to R804 that do not form the divalent group represented by the formula (82) and R811 to R814 represents a monovalent group represented by the following formula (84),
In the formula (84),
In the formula (8), the positions for the divalent group represented by the formula (82) and the divalent group represented by the formula (83) to be formed are not specifically limited but the divalent groups may be formed at any possible positions on R801 to R808.
In an exemplary embodiment, a compound represented by the formula (8) is represented by one of the following formulae (81-1) to (81-6).
In the formula (81-1) to (81-6),
In an exemplary embodiment, a compound represented by the formula (8) is represented by one of the following formulae (81-7) to (81-18).
In the formula (81-7) to (81-18),
A monovalent group represented by the formula (84) is preferably represented by the following formula (85) or (86).
In the formula (85),
In the formula (86), Ar801, L801, and L803 represent the same as Ar801, L801, and L803, respectively, in the formula (84), and HAr801 represents a structure represented by the following formula (87).
In the formula (87),
Specific examples of a compound represented by the formula (8) include compounds described in International Publication No. WO 2014/104144 and the following compounds.
(Compound Represented by Formula (9))
A compound represented by the formula (9) is described below.
In the formula (9),
In the formula (92),
At least one ring selected from the group consisting of the A91 ring and the A92 ring is bonded to * of the structure represented by the formula (92). More specifically, in an exemplary embodiment, a ring carbon atom of the aromatic hydrocarbon ring or a ring atom of the heterocycle of the A91 ring is bonded to * of the structure represented by the formula (92). Furthermore, in an exemplary embodiment, a ring carbon atom of the aromatic hydrocarbon ring or a ring atom of the heterocycle of the A92 ring is bonded to * of the structure represented by the formula (92).
In an exemplary embodiment, one or both of the A91 ring and the A92 ring are bonded to a group represented by the following formula (93).
In the formula (93),
In an exemplary embodiment, in addition to the A91 ring, a ring carbon atom of the aromatic hydrocarbon ring or a ring atom of the heterocycle of the A92 ring is bonded to * of the structure represented by the formula (92). In this case, the structure represented by the formula (92) may be mutually the same or different.
In an exemplary embodiment, R91 and R92 each independently represent a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In an exemplary embodiment, R91 and R92 are mutually bonded to form a fluorene structure.
In an exemplary embodiment, the A91 ring and the A92 ring each independently represent a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, for example, a substituted or unsubstituted benzene ring.
In an exemplary embodiment, the A93 ring is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, for example, a substituted or unsubstituted benzene ring.
In an exemplary embodiment, X9 represents an oxygen atom or a sulfur atom.
Specific examples of a compound represented by the formula (9) include the following compounds.
Compound Represented by Formula (10)
A compound represented by the formula (10) is described below.
In the formula (10),
In an exemplary embodiment, Ar1001 represents a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In an exemplary embodiment, the Ax3 ring is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, for example, a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted anthracene ring.
In an exemplary embodiment, R1003 and R1004 each independently represent a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
In an exemplary embodiment, ax is 1.
Specific examples of a compound represented by the formula (10) include the following compounds.
In an exemplary embodiment, the emitting layer contains the compound represented by the formula (120), and as a fluorescent compound (the compound M1) at least one compound selected from the group consisting of compounds represented by the formula (100), compounds represented by the formula (4), compounds represented by the formula (5), compounds represented by the formula (7), compounds represented by the formula (8), compounds represented by the formula (9), and compounds represented by the following formula (63a).
In the formula (63a),
At least one combination of adjacent two or more of R631 to R651 are mutually bonded to form a substituted or unsubstituted monocyclic ring, are mutually bonded to form a substituted or unsubstituted fused ring, or are not mutually bonded,
In an exemplary embodiment, a compound represented by the formula (4) is a compound represented by the formula (41-3), the formula (41-4), or the formula (41-5), and the A1 ring in the formula (41-5) is a substituted or unsubstituted fused aromatic hydrocarbon ring having 10 to 50 ring carbon atoms or a substituted or unsubstituted fused heterocycle having 8 to 50 ring atoms.
In an exemplary embodiment, a substituted or unsubstituted fused aromatic hydrocarbon ring having 10 to 50 ring carbon atoms in the formula (41-3), the formula (41-4), and the formula (41-5) is a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted anthracene ring, or a substituted or unsubstituted fluorene ring, and
In an exemplary embodiment, a substituted or unsubstituted fused aromatic hydrocarbon ring having 10 to 50 ring carbon atoms in the formula (41-3), the formula (41-4), or the formula (41-5) is a substituted or unsubstituted naphthalene ring, a substituted or unsubstituted fluorene ring, and
In an exemplary embodiment, a compound represented by the formula (4) is selected from the group consisting of a compound represented by the following formula (461), a compound s represented by the following formula (462), a compound represented by the following formula (463), a compound represented by the following formula (464), a compound represented by the following formula (465), a compound represented by the following formula (466), and a compound represented by the following formula (467).
In the formula (461) to (467),
In an exemplary embodiment, R421 to R427 and R440 to R448 each independently represent a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
In an exemplary embodiment, R421 to R427 and R440 to R447 are each independently selected from the group consisting of a hydrogen atom, substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, and substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.
In an exemplary embodiment, a compound represented by the formula (41-3) is a compound represented by the following formula (41-3-1).
In the formula (41-3-1), R423, R425, R426, R442, R444, and R445 represent the same as R423, R425, R426, R442, R444, and R445, respectively, in the formula (41-3).
In an exemplary embodiment, a compound represented by the formula (41-3) is a compound represented by the following formula (41-3-2).
In the formula (41-3-2), R421 to R427 and R440 to R448 represent the same as R421 to R427 and R440 to R448, respectively, in the formula (41-3),
In an exemplary embodiment, any two of R421 to R427 and R440 to R446 in the formula (41-3-2) represent a group represented by —N(R906)(R907).
In an exemplary embodiment, a compound represented by the formula (41-3-2) is a compound represented by the following formula (41-3-3).
In the formula (41-3-3), R421 to R424, R440 to R443, R447, and R448 represent the same as R421 to R424, R440 to R443, R447, and R448, respectively, in the formula (41-3), and RA, RB, RC, and RD each independently represent a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.
In an exemplary embodiment, a compound represented by the formula (41-3-3) is a compound represented by the following formula (41-3-4).
In the formula (41-3-4), R447, R448, RA, RB, RC, and RD represent the same as R447, R448, RA, RB, RC, and RD, respectively, in the formula (41-3-3).
In an exemplary embodiment, RA, RB, RC, and RD each independently represent a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.
In an exemplary embodiment, RA, RB, RC, and RD each independently represent a substituted or unsubstituted phenyl group.
In an exemplary embodiment, R447 and R448 represent a hydrogen atom.
In an exemplary embodiment, a substituent for “substituted or unsubstituted” group in each of the formulae is an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted alkenyl group having 2 to 50 carbon atoms, an unsubstituted alkynyl group having 2 to 50 carbon atoms, an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, —Si(R901a)(R902a)(R903a), —O—(R904a), —S—(R905a), —N(R906a)(R907a), a halogen atom, a cyano group, a nitro group, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms,
In an exemplary embodiment, a substituent for “substituted or unsubstituted” group in each of the formulae is an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 50 ring atoms.
In an exemplary embodiment, a substituent for “substituted or unsubstituted” group in each of the formulae is an unsubstituted alkyl group having 1 to 18 carbon atoms, an unsubstituted aryl group having 6 to 18 ring carbon atoms, or an unsubstituted heterocyclic group having 5 to 18 ring atoms.
In the organic EL device according to the fifth exemplary embodiment, preferably, the emitting layer further contains a fluorescent compound (the compound M1), and the compound M1 is a compound that emits light with a main peak wavelength in the range of 430 nm to 480 nm.
A main peak wavelength of a compound is measured by the following method. A toluene solution of a measurement target compound at a concentration ranging from 10−6 mol/L to 10−5 mol/L is prepared and put in a quartz cell. An emission spectrum (ordinate axis: emission intensity, abscissa axis: wavelength) of the thus-obtained sample is measured at a normal temperature (300K). The emission spectrum is measurable using a spectrophotometer (machine name: F-7000) manufactured by Hitachi High-Tech Science Corporation. It should be noted that the machine for measuring the emission spectrum is not limited to the machine used herein.
A peak wavelength of the emission spectrum exhibiting the maximum luminous intensity is defined as a main peak wavelength. It should be noted that the main peak wavelength is sometimes referred to as a fluorescence main peak wavelength (FL-peak) herein.
In the organic EL device according to the fifth exemplary embodiment, when the emitting layer contains a compound represented by the formula (120) and a fluorescent compound (the compound M1), the compound represented by the formula (120) is preferably a host material (sometimes referred to as a matrix material), and the fluorescent compound (the compound M1) is preferably a dopant material (sometimes referred to as a guest material, an emitter, or a luminescent material).
In the organic EL device according to the fifth exemplary embodiment, when the emitting layer contains a compound represented by the formula (120) as a host material and a fluorescent compound (the compound M1), a singlet energy S1 of the host material is preferably larger than a singlet energy S1 of the fluorescent compound (the compound M1).
The singlet energy S1 means the energy difference between the lowest singlet state and the ground state.
Singlet Energy S1
A method for measuring the singlet energy S1 using a solution (sometimes referred to as a solution method) may be the following method.
A toluene solution of a measurement target compound at a concentration ranging from 10−5 mol/L to 10−4 mol/L is prepared and put in a quartz cell. An absorption spectrum (ordinate axis: absorption intensity, abscissa axis: wavelength) of the thus-obtained sample is measured at a normal temperature (300K). A tangent is drawn to the fall of the absorption spectrum close to the long-wavelength region, and a wavelength value λedge (nm) at an intersection of the tangent and the abscissa axis is assigned to a conversion equation (F2) below to calculate the singlet energy.
S
1 [eV]=1239.85/λedge Conversion Equation (F2):
Any device for measuring absorption spectrum is usable. For instance, a spectrophotometer (U3310 manufactured by Hitachi, Ltd.) is usable.
The tangent to the fall of the absorption spectrum close to the long-wavelength region is drawn as follows. While moving on a curve of the absorption spectrum from the local maximum value closest to the long-wavelength region, among the local maximum values of the absorption spectrum, in a long-wavelength direction, a tangent at each point on the curve is checked. An inclination of the tangent is decreased and increased in a repeated manner as the curve fell (i.e., a value of the ordinate axis is decreased). A tangent drawn at a point where the inclination of the curve is the local minimum closest to the long-wavelength region (except when absorbance is 0.1 or less) is defined as the tangent to the fall of the absorption spectrum close to the long-wavelength region.
The local maximum absorbance of 0.2 or less is not counted as the above-mentioned local maximum absorbance closest to the long-wavelength region.
The emitting layer preferably contains no phosphorescent material (dopant material).
The emitting layer preferably do not contain a heavy metal complex and a phosphorescent rare earth metal complex. Examples of the heavy metal complex include iridium complexes, osmium complexes, and platinum complexes.
The emitting layer also preferably does not contain a metal complex.
Thickness of Emitting Layer
The emitting layer of the organic EL device according to the fifth exemplary embodiment preferably has a thickness in the range of 5 to 50 nm, more preferably 7 to 50 nm, further preferably 10 to 50 nm. An emitting layer with a thickness of 5 nm or more is easy to form, and the chromaticity of the emitting layer can be easily adjusted. When the emitting layer has a thickness of 50 nm or less, it is easy to reduce an increase in drive voltage.
Content Ratios of Compounds in Emitting Layer
When the emitting layer contains the compound according to the first exemplary embodiment (the compound represented by the formula (12X)) as a host material and a fluorescent compound (the compound M1), the content ratios of the compound according to the first exemplary embodiment and the fluorescent compound (the compound M1) in the emitting layer are preferably in the following ranges, for example.
When the emitting layer contains the compound according to the second exemplary embodiment (the compound represented by the formula (120)) as a host material and a fluorescent compound (the compound M1), the content ratios of the compound according to the second exemplary embodiment (the compound represented by the formula (120)) and the fluorescent compound (the compound M1) in the emitting layer are preferably in the following ranges, for example.
When the emitting layer contains the compound according to the third exemplary embodiment (at least one of compounds represented by one of the formulae (1) to (3)) as a host material and a fluorescent compound (the compound M1), the compound according to the third exemplary embodiment and the fluorescent compound (the compound M1) in the emitting layer are preferably in the following ranges, for example.
The content ratio of the compound according to the first exemplary embodiment, the compound according to the second exemplary embodiment, or the compound according to the third exemplary embodiment preferably ranges from 80% to 99% by mass, more preferably 90% to 99% by mass, further preferably 95% to 99% by mass.
The content ratio of the fluorescent compound (the compound M1) preferably ranges from 1% to 10% by mass, more preferably 1% to 7% by mass, further preferably 1% to 5% by mass.
The upper limit of the total content ratio of the compound according to the first exemplary embodiment, the compound according to the second exemplary embodiment, or the compound according to the third exemplary embodiment and the fluorescent compound (the compound M1) in the emitting layer is 100% by mass.
In the fifth exemplary embodiment, It is not excluded that the emitting layer contains a material other than the compound according to the first exemplary embodiment, the compound according to the second exemplary embodiment, the compound according to the third exemplary embodiment, and the fluorescent compound (the compound M1).
The emitting layer may contain one or two or more compounds according to the first exemplary embodiment (the compound represented by the formula (12X)).
The emitting layer may contain one or two or more compounds according to the second exemplary embodiment (compounds represented by the formula (120)).
The emitting layer may contain one or two or more compounds according to the third exemplary embodiment (at least one of compounds represented by one of the formulae (1) to (3)).
The emitting layer may contain one or two or more fluorescent compounds (compounds M1).
The structure of the organic EL device 1 is further described below. Reference numerals and letters may be hereinafter omitted.
Substrate
The substrate is used as a support for the organic EL device. For instance, glass, quartz, plastics and the like are usable for the substrate. A flexible substrate is also usable. The flexible substrate is a bendable substrate, which is exemplified by a plastic substrate. Examples of the material for the plastic substrate include polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. Moreover, an inorganic vapor deposition film is also usable.
Anode
Metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a large work function (specifically, 4.0 eV or more) is preferably used as the anode formed on the substrate. Specific examples of the material include ITO (Indium Tin Oxide), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide, and graphene. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chrome (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), and nitrides of a metal material (e.g., titanium nitride) are usable.
These materials are typically deposited by a sputtering method. For instance, the indium oxide-zinc oxide can be formed into a film by the sputtering method using a target in which zinc oxide in a range from 1 mass % to 10 mass % is added to indium oxide. Moreover, for instance, the indium oxide containing tungsten oxide and zinc oxide can be formed by the sputtering method using a target in which tungsten oxide in a range from 0.5 mass % to 5 mass % and zinc oxide in a range from 0.1 mass % to 1 mass % are added to indium oxide. In addition, the anode may be formed by a vacuum deposition method, a coating method, an inkjet method, a spin coating method or the like.
Among the organic layers formed on the anode, since the hole injecting layer adjacent to the anode is formed of a composite material into which holes are easily injectable irrespective of the work function of the anode, a material usable as an electrode material (e.g., metal, an alloy, an electroconductive compound, a mixture thereof, and the elements belonging to the group 1 or 2 of the periodic table) is also usable for the anode.
A material having a small work function such as elements belonging to Groups 1 and 2 in the periodic table of the elements, specifically, an alkali metal such as lithium (Li) and cesium (Cs), an alkaline earth metal such as magnesium (Mg), calcium (Ca) and strontium (Sr), alloys (e.g., MgAg and AlLi) including the alkali metal or the alkaline earth metal, a rare earth metal such as europium (Eu) and ytterbium (Yb), alloys including the rare earth metal are also usable for the anode. It should be noted that the vacuum deposition method and the sputtering method are usable for forming the anode using the alkali metal, alkaline earth metal and the alloy thereof. Further, when a silver paste is used for the anode, the coating method and the inkjet method are usable.
Cathode
It is preferable to use metal, an alloy, an electroconductive compound, a mixture thereof, or the like having a small work function (specifically, 3.8 eV or less) for the cathode. Examples of the material for the cathode include elements belonging to Groups 1 and 2 in the periodic table of the elements, specifically, the alkali metal such as lithium (Li) and cesium (Cs), the alkaline earth metal such as magnesium (Mg), calcium (Ca) and strontium (Sr), alloys (e.g., MgAg and AlLi) including the alkali metal or the alkaline earth metal, the rare earth metal such as europium (Eu) and ytterbium (Yb), and alloys including the rare earth metal.
It should be noted that the vacuum deposition method and the sputtering method are usable for forming the cathode using the alkali metal, alkaline earth metal and the alloy thereof. Further, when a silver paste is used for the cathode, the coating method and the inkjet method are usable.
By providing the electron injecting layer, various conductive materials such as Al, Ag, ITO, graphene, and indium oxide-tin oxide containing silicon or silicon oxide may be used for forming the cathode regardless of the work function. The conductive materials can be formed into a film using the sputtering method, inkjet method, spin coating method and the like.
Hole Injecting Layer
The hole injecting layer is a layer containing a substance exhibiting a high hole injectability. Examples of the substance exhibiting a high hole injectability include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chrome oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, and manganese oxide.
In addition, the examples of the substance exhibiting a high hole injectability further include: an aromatic amine compound, which is a low-molecule organic compound, such as 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4′,4″-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4′-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4′-bis(N-{4-[N′-(3-methylphenyl)-N′-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1); and dipyrazino[2,3-f:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN).
In addition, a high polymer compound (e.g., oligomer, dendrimer and polymer) is usable as the substance exhibiting a high hole injectability. Examples of the high-molecule compound include poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N′-[4-(4-diphenylamino)phenyl]phenyl-N′-phenylamino}phenyl)methacrylamide] (abbreviation: PTPDMA), and poly[N,N′-bis(4-butylphenyl)-N,N′-bis(phenyl)benzidine] (abbreviation: Poly-TPD). Moreover, an acid-added high polymer compound such as poly(3,4-ethylenedioxythiophene)/poly(styrene sulfonic acid) (PEDOT/PSS) and polyaniline/poly(styrene sulfonic acid) (PAni/PSS) are also usable.
Hole Transporting Layer
The hole transporting layer is a layer containing a highly hole-transporting substance. An aromatic amine compound, carbazole derivative, anthracene derivative and the like are usable for the hole transporting layer. Specific examples of a material for the hole transporting layer include an aromatic amine compound such as 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1′-biphenyl]-4,4′-diamine (abbreviation: TPD), 4-phenyl-4′-(9-phenylfluorene-9-yl)triphenylamine (abbreviation: BAFLP), 4,4′-bis[N-(9,9-dimethylfluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4′,4″-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4,4′-bis[N-(spiro-9,9′-bifluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). The above-described substances mostly have a hole mobility of 10−6 cm2/(Vs) or more.
For the hole transporting layer, a carbazole derivative such as CBP, 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (PCzPA) and an anthracene derivative such as t-BuDNA, DNA, and DPAnth may be used. A high polymer compound such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) is also usable.
However, in addition to the above substances, any substance exhibiting a higher hole transportability than an electron transportability may be used. It should be noted that the layer containing the substance exhibiting a high hole transportability may be not only a single layer but also a laminate of two or more layers formed of the above substance(s).
Electron Transporting Layer
The electron transporting layer is a layer containing a highly electron-transporting substance. For the electron transporting layer, 1) a metal complex such as an aluminum complex, beryllium complex, and zinc complex, 2) a hetero aromatic compound such as imidazole derivative, benzimidazole derivative, azine derivative, carbazole derivative, and phenanthroline derivative, and 3) a high polymer compound are usable. Specifically, as a low-molecule organic compound, a metal complex such as Alq, tris(4-methyl-8-quinolinato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq2), BAlq, Znq, ZnPBO and ZnBTZ is usable. In addition to the metal complex, a heteroaromatic compound such as 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), and 4,4′-bis(5-methylbenzoxazole-2-yl)stilbene (abbreviation: BzOs) is usable. In the exemplary embodiment, a benzimidazole compound is suitably usable. The above-described substances mostly have an electron mobility of 10−6 cm2/(Vs) or more. It should be noted that any substance other than the above substance may be used for the electron transporting layer as long as the substance exhibits a higher electron transportability than the hole transportability. The electron transporting layer may be provided in the form of a single layer or a laminate of two or more layers of the above substance(s).
Specific examples of a compound that can be used for the electron transporting layer include the following compounds. However, the invention is not limited to the specific examples of the compound.
A high-molecular-weight compound may also be used for the electron transporting layer, for example, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) or poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy).
Electron Injecting Layer
The electron injecting layer is a layer containing a highly electron-injectable substance. Examples of a material for the electron injecting layer include an alkali metal, alkaline earth metal and a compound thereof, examples of which include lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), and lithium oxide (LiOx). In addition, the alkali metal, alkaline earth metal or the compound thereof may be added to the substance exhibiting the electron transportability in use. Specifically, for instance, magnesium (Mg) added to Alq may be used. In this case, the electrons can be more efficiently injected from the cathode.
Alternatively, the electron injecting layer may be provided by a composite material in a form of a mixture of the organic compound and the electron donor. Such a composite material exhibits excellent electron injectability and electron transportability since electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material excellent in transporting the generated electrons. Specifically, the above examples (e.g., the metal complex and the hetero aromatic compound) of the substance forming the electron transporting layer are usable. As the electron donor, any substance exhibiting electron donating property to the organic compound is usable. Specifically, the electron donor is preferably alkali metal, alkaline earth metal and rare earth metal such as lithium, cesium, magnesium, calcium, erbium and ytterbium. The electron donor is also preferably alkali metal oxide and alkaline earth metal oxide such as lithium oxide, calcium oxide, and barium oxide. Moreover, a Lewis base such as magnesium oxide is usable. Further, the organic compound such as tetrathiafulvalene (abbreviation: TTF) is usable.
Layer Forming Method
A method for forming each layer of the organic EL device in the exemplary embodiment is subject to no limitation except for the above particular description. However, known methods of dry film-forming such as vacuum deposition, sputtering, plasma or ion plating and wet film-forming such as spin coating, dipping, flow coating or ink-jet are applicable.
Film Thickness
A film thickness of each of the organic layers of the organic EL device in the exemplary embodiment is not limited unless otherwise specified in the above. In general, the thickness preferably ranges from several nanometers to 1 μm because excessively small film thickness is likely to cause defects (e.g. pin holes) and excessively large thickness leads to the necessity of applying high voltage and consequent reduction in efficiency.
The fifth exemplary embodiment can provide an organic electroluminescence device with improved luminous efficiency.
An organic electroluminescence device according to a sixth exemplary embodiment includes an anode, a cathode, a first emitting layer between the anode and the cathode, and a second emitting layer between the first emitting layer and the cathode. The first emitting layer has at least one group represented by the formula (11) and contains a first compound represented by the formula (1A) as a first host material, and the second emitting layer contains a second compound represented by the following formula (2) as a second host material. In the organic EL device according to the sixth exemplary embodiment, the first emitting layer is in direct contact with the second emitting layer.
In the organic EL device according to the sixth exemplary embodiment, the first emitting layer contains, as a first compound represented by the formula (1), the compound according to the first exemplary embodiment (the compound represented by the formula (12X)), the compound according to the second exemplary embodiment (the compound represented by the formula (120)), or the compound according to the third exemplary embodiment (at least one of the compounds represented by one of the formulae (1) to (3)).
The compound according to the first exemplary embodiment (the compound represented by the formula (12X)) is an embodiment of the first compound.
The compound according to the second exemplary embodiment (the compound represented by the formula (120)) is an embodiment of the first compound.
The compound according to the third exemplary embodiment (the compound represented by the formula (1), (2), or (3)) is an embodiment of the first compound.
Thus, the first emitting layer contains, as a first host material, the compound according to the first exemplary embodiment, the compound according to the second exemplary embodiment, or the compound according to the third exemplary embodiment.
In the organic EL device according to the sixth exemplary embodiment, the first emitting layer contains the compound according to the first exemplary embodiment (the compound represented by the formula (12X)) as a first host material, the second emitting layer contains a second compound represented by the following formula (2) as a second host material, and the first emitting layer is in direct contact with the second emitting layer.
In the organic EL device according to the sixth exemplary embodiment, the first emitting layer contains the compound according to the second exemplary embodiment (the compound represented by the formula (120)) as a first host material, the second emitting layer contains a second compound represented by the following formula (2) as a second host material, and the first emitting layer is in direct contact with the second emitting layer.
In the organic EL device according to the sixth exemplary embodiment, the first emitting layer contains the compound according to the third exemplary embodiment (at least one of compounds represented by one of the formulae (1) to (3)) as a first host material, the second emitting layer contains a second compound represented by the following formula (2) as a second host material, and the first emitting layer is in direct contact with the second emitting layer.
Herein, the “host material” refers to, for instance, a material that accounts for “50 mass % or more of the layer.” Accordingly, for instance, the first emitting layer contains 50 mass % or more of the first compound represented by the formula (1A) below with respect to a total mass of the first emitting layer. The second emitting layer contains 50 mass % or more of the second compound represented by the formula (2) below with respect to a total mass of the second emitting layer.
Emission Wavelength of Organic EL Device
The organic electroluminescence device according to the sixth exemplary embodiment preferably emits light with a main peak wavelength in the range of 430 nm to 480 nm when driven.
The main peak wavelength of light emitted from an organic EL device driven is measured as described below. Voltage is applied on the organic EL devices such that a current density becomes 10 mA/cm2, where spectral radiance spectrum is measured by a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). A peak wavelength of an emission spectrum, at which the luminous intensity of the resultant spectral radiance spectrum is at the maximum, is measured and defined as the main peak wavelength (unit: nm).
The organic EL device according to the sixth exemplary embodiment may have at least one organic layer in addition to the first emitting layer and the second emitting layer. The organic layer may be at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, an emitting layer, an electron injecting layer, an electron transporting layer, a hole blocking layer, and an electron blocking layer.
In the organic EL device according to the sixth exemplary embodiment, the organic layer may consist of the first emitting layer and the second emitting layer or may further have at least one layer selected from the group consisting of a hole injecting layer, a hole transporting layer, an electron injecting layer, an electron transporting layer, a hole blocking layer, an electron blocking layer, and the like.
The organic EL device according to the sixth exemplary embodiment preferably has a hole transporting layer between the anode and the first emitting layer.
The organic EL device according to the sixth exemplary embodiment preferably has an electron transporting layer between the cathode and the second emitting layer.
The sixth exemplary embodiment can provide an organic electroluminescence device with improved luminous efficiency.
In the organic EL device according to the sixth exemplary embodiment, the first emitting layer containing the first compound (the compound according to the first exemplary embodiment, the compound according to the second exemplary embodiment, or the compound according to the third exemplary embodiment) as a first host material is in direct contact with the second emitting layer containing the second compound represented by the following formula (2) as a second host material. The first emitting layer and the second emitting layer layered in this manner can effectively utilize singlet excitons and triplet excitons generated and consequently can improve the luminous efficiency of the organic EL device.
An organic EL device 1A includes a light-transmissive substrate 2, an anode 3, a cathode 4, and an organic layer 10A between the anode 3 and the cathode 4. The organic layer 10A includes a hole injecting layer 6, a hole transporting layer 7, a first emitting layer 51, a second emitting layer 52, an electron transporting layer 8, and an electron injecting layer 9 layered in this order on the anode 3. The first emitting layer 51 is in direct contact with the second emitting layer 52.
Second Compound
In the organic EL device according to the sixth exemplary embodiment, the second compound is a compound represented by the following formula (2).
In the formula (2),
In the second compound according to the sixth exemplary embodiment, R901, R902, R903, R904, R905, R906, R907, R801, and R802 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,
In the organic EL device according to the sixth exemplary embodiment, it is preferable that R201 to R208 each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a group represented by —Si(R901)(R902)(R903), a group represented by —O—(R904), a group represented by —S—(R905), a group represented by —N(R906)(R907), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, a group represented by —C(═O)R801, a group represented by —COOR802, a halogen atom, a cyano group, or a nitro group,
In the organic EL device according to the sixth exemplary embodiment, it is preferable that L201 and L202 each independently represent a single bond, or a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, and Ar201 and Ar202 each independently represent a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In the organic EL device according to the sixth exemplary embodiment, Ar201 and Ar202 preferably each independently represent a phenyl group, a naphthyl group, a phenanthryl group, a biphenyl group, a terphenyl group, a diphenylfluorenyl group, a dimethylfluorenyl group, a benzodiphenylfluorenyl group, a benzodimethylfluorenyl group, a dibenzofuranyl group, a dibenzothienyl group, a naphthobenzofuranyl group, or a naphthobenzothienyl group.
In the organic EL device according to the sixth exemplary embodiment, the second compound represented by the formula (2) is preferably a compound represented by the formula (201), the formula (202), the formula (203), the formula (204), the formula (205), the formula (206), the formula (207), the formula (208), or the formula (209) described below.
In the formula (201) to (209), L201 and Ar201 represent the same as L201 and Ar201, respectively, in the formula (2), and R201 to R208 represent the same as R201 to R208, respectively, in the formula (2).
The second compound represented by the formula (2) is also preferably a compound represented by the formula (221), the formula (222), the formula (223), the formula (224), the formula (225), the formula (226), the formula (227), the formula (228), or the formula (229) described below.
In the formula (221), the formula (222), the formula (223), the formula (224), the formula (225), the formula (226), the formula (227), the formula (228), and the formula (229),
The second compound represented by the formula (2) is also preferably a compound represented by the formula (241), the formula (242), the formula (243), the formula (244), the formula (245), the formula (246), the formula (247), the formula (248), or the formula (249) described below.
In the formula (241), the formula (242), the formula (243), the formula (244), the formula (245), the formula (246), the formula (247), the formula (248), and the formula (249),
In the second compound represented by the formula (2), R201 to R208 that are not groups represented by the formula (21) preferably each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a group represented by —Si(R901)(R902)(R903).
Preferably, L101 represents a single bond, or an unsubstituted arylene group having 6 to 22 ring carbon atoms, and Ar101 represents a substituted or unsubstituted aryl group having 6 to 22 ring carbon atoms.
In the organic EL device according to the sixth exemplary embodiment, in the second compound represented by the formula (2), R201 to R208 preferably each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a group represented by —Si(R901)(R902)(R903).
In the organic EL device according to the sixth exemplary embodiment, in the second compound represented by the formula (2), R201 to R208 preferably represent a hydrogen atom.
In the second compound, the groups specified to be “substituted or unsubstituted” are each preferably an “unsubstituted” group.
In the organic EL device according to the sixth exemplary embodiment, for example, Ar201 in the second compound represented by the formula (2) represents a substituted or unsubstituted dibenzofuranyl group.
In the organic EL device according to the sixth exemplary embodiment, for example, Ar201 in the second compound represented by the formula (2) represents an unsubstituted dibenzofuranyl group.
In the organic EL device according to the sixth exemplary embodiment, for example, the second compound represented by the formula (2) has at least one hydrogen, and at least one of the hydrogen(s) is deuterium.
In the organic EL device according to the sixth exemplary embodiment, for example, L201 in the second compound represented by the formula (2) represents one of TEMP-63 to TEMP-68.
In the organic EL device according to the sixth exemplary embodiment, for example, Ar201 in the second compound represented by the formula (2) represents at least one group selected from the group consisting of substituted or unsubstituted anthryl group, benzoanthryl group, phenanthryl group, benzophenanthryl group, phenalenyl group, pyrenyl group, chrysenyl group, benzochrysenyl group, triphenylenyl group, benzotriphenylenyl group, tetracenyl group, pentacenyl group, fluoranthenyl group, benzofluoranthenyl group, and perylenyl group.
In the organic EL device according to the sixth exemplary embodiment, for example, Ar201 in the second compound represented by the formula (2) represents a substituted or unsubstituted fluorenyl group.
In the organic EL device according to the sixth exemplary embodiment, for example, Ar201 in the second compound represented by the formula (2) represents a substituted or unsubstituted xanthenyl group.
In the organic EL device according to the sixth exemplary embodiment, for example, Ar201 in the second compound represented by the formula (2) represents a substituted or unsubstituted benzoxanthenyl group.
Method for Producing Second Compound
The second compound can be produced by a known method. The second compound can also be produced in accordance with a known method by using a known alternative reaction and raw materials suitable for the target compound.
Specific examples of the second compound include the following compounds. However, the invention is not limited to the specific examples of the second compound.
Fluorescent Compound (Compound M1)
In the organic EL device according to the sixth exemplary embodiment, preferably, the first emitting layer contains the compound according to the first exemplary embodiment (the compound represented by the formula (12X)) as a first host material and also contains a fluorescent compound (the compound M1).
In the organic EL device according to the sixth exemplary embodiment, preferably, the first emitting layer contains the compound according to the second exemplary embodiment (the compound represented by the formula (120)) as a first host material and also contains a fluorescent compound (the compound M1).
In the organic EL device according to the sixth exemplary embodiment, preferably, the first emitting layer contains the compound according to the third exemplary embodiment (at least one of compounds represented by one of the formulae (1) to (3)) as a first host material and also contains a fluorescent compound (the compound M1).
The fluorescent compound (the compound M1) represents the same as the compound M1 described in the fifth exemplary embodiment. Thus, in the organic EL device according to the sixth exemplary embodiment, the fluorescent compound (the compound M1) is preferably at least one compound selected from the group consisting of the compounds represented by the formula (100), the compounds represented by the formula (3), the compounds represented by the formula (4), the compounds represented by the formula (5), the compounds represented by the formula (6), the compounds represented by the formula (7), the compounds represented by the formula (8), the compounds represented by the formula (9), and the compounds represented by the formula (10).
In the organic EL device according to the sixth exemplary embodiment, when the first emitting layer contains the compound according to the first exemplary embodiment (the compound represented by the formula (12X)), the compound according to the second exemplary embodiment (the compound represented by the formula (120)), or the compound according to the third exemplary embodiment (at least one of compounds represented by one of the formulae (1) to (3)) as the first compound and a fluorescent compound (the compound M1), the first compound is preferably a host material (sometimes referred to as a matrix material), and the fluorescent compound (the compound M1) is preferably a dopant material (sometimes referred to as a guest material, an emitter, or a luminescent material).
In the organic EL device according to the sixth exemplary embodiment, when the first emitting layer contains the compound according to the first exemplary embodiment (the compound represented by the formula (12X)), the compound according to the second exemplary embodiment (the compound represented by the formula (120)), or the compound according to the third exemplary embodiment (at least one of compounds represented by one of the formulae (1) to (3)) as the first compound and a fluorescent compound (the compound M1), the singlet energy S1(H1) of the first compound and the singlet energy S1(M1) of the fluorescent compound preferably satisfy the relationship of a numerical formula (Numerical Formula 1) below.
S
1(H1)>S1(M1) (Numerical Formula 1)
In the organic EL device according to the sixth exemplary embodiment, when the second emitting layer contains the second compound and a fluorescent compound (the compound M1), the singlet energy S1(H2) of the second compound and the singlet energy S1(M1) of the fluorescent compound (the compound M1) preferably satisfy a numerical formula (Numerical Formula 2) below.
S
1(H2)>S1(M1) (Numerical Formula 2)
An electronic device according to a seventh exemplary embodiment is installed with any one of the organic EL devices according to the above exemplary embodiment. Examples of the electronic device include a display device and a light-emitting unit. Examples of the display device include a display component (e.g., an organic EL panel module), TV, mobile phone, tablet and personal computer. Examples of the light-emitting unit include an illuminator and a vehicle light.
The scope of the invention is not limited by the above-described exemplary embodiments but includes any modification and improvement as long as such modification and improvement are compatible with the invention.
For instance, the number of emitting layers is not limited to two, and more than two emitting layers may be provided and laminated with each other. When an organic EL device has more than two emitting layers, it is sufficient that at least one emitting layer contains a compound represented by the formula (120) (one example of the first compound). For example, the other emitting layer(s) may be a fluorescent emitting layer or a phosphorescent emitting layer utilizing light emission due to a direct electronic transition from a triplet excited state to the ground state.
When the organic EL device includes a plurality of emitting layers, these emitting layers may be mutually adjacently provided, or may form a so-called tandem organic EL device, in which a plurality of emitting units are layered via an intermediate layer.
For instance, a blocking layer may be provided adjacent to at least one of a side of the emitting layer close to the anode or a side of the emitting layer close to the cathode. The blocking layer is preferably provided in contact with the emitting layer to block at least any of holes, electrons, or excitons.
For instance, when the blocking layer is provided in contact with the side of the emitting layer close to the cathode, the blocking layer permits transport of electrons and blocks holes from reaching a layer provided closer to the cathode (e.g., the electron transporting layer) beyond the blocking layer. When the organic EL device includes the electron transporting layer, the blocking layer is preferably interposed between the emitting layer and the electron transporting layer.
When the blocking layer is provided in contact with the side of the emitting layer close to the anode, the blocking layer permits transport of holes and blocks electrons from reaching a layer provided closer to the anode (e.g., the hole transporting layer) beyond the blocking layer. When the organic EL device includes the hole transporting layer, the blocking layer is preferably interposed between the emitting layer and the hole transporting layer.
Alternatively, the blocking layer may be provided adjacent to the emitting layer so that excitation energy does not leak out from the emitting layer toward neighboring layer(s). The blocking layer blocks excitons generated in the emitting layer from being transferred to a layer(s) (e.g., the electron transporting layer and the hole transporting layer) closer to the electrode(s) beyond the blocking layer.
The emitting layer is preferably bonded to a blocking layer.
Specific structure, shape and the like of the components in the invention may be designed in any manner as long as an object of the invention can be achieved.
A compound represented by the formula (120) according to Example 1 has the following structure.
Other compounds used to produce organic EL devices according to Example 1 and Comparative Example 1 have the following structures.
Production 1 of Organic EL device
An organic EL device was produced and evaluated as described below.
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, manufactured by Geomatec Co., Ltd.) having an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonic-cleaned in isopropyl alcohol for five minutes, and then UV-ozone-cleaned for 30 minutes. The ITO transparent electrode had a thickness of 130 nm.
The cleaned glass substrate having the transparent electrode line was attached to a substrate holder of a vacuum deposition apparatus. First, a compound HI-1 was deposited on a surface, on which the transparent electrode line was formed, to cover the transparent electrode, thus forming a hole injecting layer (HI) with a thickness of 5 nm.
After the formation of the hole injecting layer, the compound HT-1 was deposited to form a first hole transporting layer (HT) with a thickness of 80 nm.
After the formation of the first hole transporting layer, a compound EBL-1 was deposited to form a second hole transporting layer (also referred to as an electron blocking layer) (EBL) with a thickness of 10 nm.
A compound BH-1 (host material (BH)) and a compound BD-1 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD-1 accounted for 4% by mass, thus forming an emitting layer with a thickness of 25 nm.
A compound HBL-1 was deposited on the emitting layer to form a first electron transporting layer (also referred to as a hole blocking layer) (HBL) with a thickness of 10 nm.
A compound BH-3 was deposited on the first electron transporting layer to form a second electron transporting layer (ET) with a thickness of 15 nm.
LiF was deposited on the second electron transporting layer to form an electron injecting layer with a thickness of 1 nm.
Metal Al was deposited on the electron injecting layer to form a cathode with a thickness of 50 nm.
A device arrangement of an organic EL device in Example 1 is roughly shown as follows.
ITO (130)/HI-1 (5)/HT-1 (80)/EBL-1 (10)/BH-1:BD-1 (25, 96%:4%)/HBL-1 (10)/BH-3 (15)/LiF (1)/Al (50)
The numerals in parentheses indicate the film thicknesses (unit: nm).
The numerals (96%:4%) represented by percentage in the same parentheses indicate a ratio (% by mass) of the host material (the compound BH-1) to the compound BD-1 in the emitting layer. Similar notations apply to the description below.
An organic EL device according to Comparative Example 1 was produced in the same manner as in Example 1 except that the compound BH-1 in the emitting layer in Example 1 was replaced with the compound listed in Table 1.
Evaluation 1 of Organic EL Device
The organic EL devices produced in Example 1 and Comparative Example 1 were evaluated as described below. Table 1 shows the evaluation results.
External Quantum Efficiency EQE
Voltage was applied on the organic EL devices so that a current density was 10 mA/cm2, where spectral radiance spectrum was measured by a spectroradiometer (CS-2000 manufactured by Konica Minolta, Inc.). The external quantum efficiency EQE (unit: %) was calculated based on the obtained spectral-radiance spectra, assuming that the spectra was provided under a Lambertian radiation.
Main Peak Wavelength λp when Device is Driven
Voltage was applied on the organic EL devices so that a current density of the organic EL device was 10 mA/cm2, where spectral radiance spectrum was measured by a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). The main peak wavelength λp (unit: nm) was calculated based on the obtained spectral radiance spectrum.
Table 1 shows that the organic EL device according to Example 1 containing the compound BH-1 as a host material in the emitting layer emitted light with a higher luminous efficiency than the organic EL device according to Comparative Example 1 containing a compound Com. BH-A as a host material in the emitting layer.
Preparation of Toluene Solution
The compound BD-1 was dissolved in toluene at a concentration of 4.9×10−6 mol/L to prepare a toluene solution of the compound BD-1.
Measurement of Fluorescent Main Peak Wavelength (FL-Peak)
A fluorescence spectrum measuring apparatus (fluorescence spectrophotometer F-7000 (manufactured by Hitachi High-Tech Science Corporation)) was used to measure a fluorescent main peak wavelength when the toluene solution of the compound BD-1 was excited at 390 nm.
The compound BD-1 had a fluorescent main peak wavelength at 442 nm.
A compound represented by the formula (120) in Example 2 has the following structure.
Other compounds used to produce an organic EL device in Example 2 have the following structures.
Production 2 of Organic EL Device
An organic EL device was produced and evaluated as described below.
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, manufactured by Geomatec Co., Ltd.) having an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonic-cleaned in isopropyl alcohol for five minutes, and then UV-ozone-cleaned for 30 minutes. The ITO transparent electrode had a thickness of 130 nm.
The cleaned glass substrate having the transparent electrode line was attached to a substrate holder of a vacuum deposition apparatus. First, a compound HA1 was deposited on a surface, on which the transparent electrode line was formed, to cover the transparent electrode, thus forming a hole injecting layer (HI) with a thickness of 5 nm.
After the formation of the hole injecting layer, the compound HT1 was deposited to form a first hole transporting layer (HT) with a thickness of 80 nm.
After the formation of the first hole transporting layer, a compound HT2 was deposited to form a second hole transporting layer (also referred to as an electron blocking layer) (EBL) with a thickness of 10 nm.
A compound BH1-11 (first host material (BH)) and a compound BD1 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD1 accounted for 2% by mass, thus forming a first emitting layer with a thickness of 5 nm.
A compound BH2 (second host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the first emitting layer such that the ratio of the compound BD1 accounted for 2% by mass, thus forming a second emitting layer with a thickness of 20 nm.
A compound ET1 was deposited on the second emitting layer to form a first electron transporting layer (also referred to as a hole blocking layer) (HBL) with a thickness of 10 nm.
A compound ET2 was deposited on the first electron transporting layer to form a second electron transporting layer (ET) with a thickness of 15 nm.
LiF was deposited on the second electron transporting layer to form an electron injecting layer with a thickness of 1 nm.
Metal Al was deposited on the electron injecting layer to form a cathode with a thickness of 80 nm.
A device arrangement of an organic EL device in Example 2 is roughly shown as follows.
ITO (130)/HA1 (5)/HT1 (80)/HT2 (10)/BH1-11:BD1 (5, 98%:2%)/BH2:BD1 (20, 98%:2%)/ET1 (10)/ET2 (15)/LiF (1)/Al (80)
Evaluation 2 of Organic EL Device
The organic EL device produced in Example 2 was evaluated as described below. Table 2 shows the evaluation results.
External Quantum Efficiency EQE
Voltage was applied on the organic EL devices so that a current density was 10 mA/cm2, where spectral radiance spectrum was measured by a spectroradiometer (CS-2000 manufactured by Konica Minolta, Inc.). The external quantum efficiency EQE (unit: %) was calculated based on the obtained spectral-radiance spectra, assuming that the spectra was provided under a Lambertian radiation.
Life LT95
Voltage was applied on the resultant organic EL devices so that a current density was 50 mA/cm2, where a time (LT95 (unit: hr)) elapsed before a luminance intensity was reduced to 95% of the initial luminance intensity was measured.
Drive Voltage
The voltage (unit: V) when electric current was applied between the anode and the cathode so that the current density was 10 mA/cm2 was measured.
Compounds represented by the formula (120) according to Examples 3 to 9 have the following structures.
Other compounds used to produce organic EL devices according to Examples 3 to 9 have the following structures.
Production 3 of Organic EL Device
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, manufactured by Geomatec Co., Ltd.) having an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonic-cleaned in isopropyl alcohol for five minutes, and then UV-ozone-cleaned for 30 minutes. The ITO transparent electrode had a thickness of 130 nm.
The cleaned glass substrate having the transparent electrode line was attached to a substrate holder of a vacuum deposition apparatus. First, a compound HT9 and a compound HA2 were co-deposited on a surface, on which the transparent electrode line was formed, to cover the transparent electrode, thus forming a hole injecting layer (HI) with a thickness of 10 nm. In the hole injecting layer, the ratio of the compound HT9 accounted for 90% by mass, and the ratio of the compound HA2 accounted for 10% by mass.
After the formation of the hole injecting layer, the compound HT9 was deposited to form a first hole transporting layer (HT) with a thickness of 85 nm.
After the formation of the first hole transporting layer, a compound HT8 was deposited to form a second hole transporting layer (also referred to as an electron blocking layer) (EBL) with a thickness of 5 nm.
A compound BH1-87 (first host material (BH)) and a compound BD2 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD2 accounted for 2% by mass, thus forming a first emitting layer with a thickness of 5 nm.
A compound BH2-7 (second host material (BH)) and the compound BD2 (dopant material (BD)) were co-deposited on the first emitting layer such that the ratio of the compound BD2 accounted for 2% by mass, thus forming a second emitting layer with a thickness of 15 nm.
A compound ET3 was deposited on the second emitting layer to form a first electron transporting layer (also referred to as a hole blocking layer) (HBL) with a thickness of 5 nm.
A compound ET8 and a compound Liq were co-deposited on the first electron transporting layer (HBL) to form a second electron transporting layer (ET) with a thickness of 25 nm. In the second electron transporting layer (ET), the ratio of the compound ET8 accounted for 50% by mass, and the ratio of the compound Liq accounted for 50% by mass. Liq is an abbreviation of (8-quinolinolato)lithium.
Liq was deposited on the second electron transporting layer to form an electron injecting layer with a thickness of 1 nm.
Metal Al was deposited on the electron injecting layer to form a cathode with a thickness of 80 nm.
A device arrangement of an organic EL device in Example 3 is roughly shown as follows.
ITO (130)/HT9:HA2 (10, 90%:10%)/HT9 (85)/HT8 (5)/BH1-87:BD2 (5, 98%:2%)/BH2-7:BD2 (15, 98%:2%)/ET3 (5)/ET8:Liq (25, 50%:50%)/Liq (1)/Al (80)
The numerals in parentheses indicate the film thicknesses (unit: nm).
The numerals (90%:10%) represented by percentage in the same parentheses indicate a ratio (% by mass) of the compound HT9 to the compound HA2 in the hole injecting layer.
The numerals (98%:2%) represented by percentage in the same parentheses indicate the ratio (% by mass) of the host material (compound BH1-87 or compound BH2-7) to the dopant material (compound BD2) in the first emitting layer or the second emitting layer. The numerals (50%:50%) represented by percentage in the same parentheses indicate the ratio (% by mass) of the compound ET8 to the compound Liq in the electron transporting layer (ET).
Organic EL devices according to Examples 4 to 9 and Comparative Examples 2 to 4 were produced in the same manner as in Example 3 except that the compound BH-87 in the emitting layer in Example 3 was replaced with the compounds listed in Table 3.
Evaluation 3 of Organic EL Device
The organic EL devices produced in Examples 3 to 8 and Comparative Examples 2 and 3 were evaluated as described below. For the organic EL devices produced in Example 9 and Comparative Example 4, only CIE1931 chromaticity was measured. Table 3 shows the evaluation results.
External Quantum Efficiency EQE
Voltage was applied on the organic EL devices so that a current density was 10 mA/cm2, where spectral radiance spectrum was measured by a spectroradiometer (CS-2000 manufactured by Konica Minolta, Inc.). The external quantum efficiency EQE (unit: %) was calculated based on the obtained spectral-radiance spectra, assuming that the spectra was provided under a Lambertian radiation.
Life LT95
Voltage was applied on the resultant organic EL devices so that a current density was 50 mA/cm2, where a time (LT95 (unit: hr)) elapsed before a luminance intensity was reduced to 95% of the initial luminance intensity was measured.
Drive Voltage
The voltage (unit: V) when electric current was applied between the anode and the cathode so that the current density was 10 mA/cm2 was measured.
CIE1931 Chromaticity
Voltage was applied on the organic EL devices so that a current density was 10 mA/cm2, where spectral radiance spectrum was measured by a spectroradiometer (CS-2000 manufactured by Konica Minolta, Inc.).
From the obtained spectral radiance spectrum, CIEx and CIEy were calculated.
Table 3 shows that Examples 3 to 8 containing a compound represented by the formula (120) as a host material in the emitting layer emitted light with a higher luminous efficiency than Comparative Examples 2 and 3 containing compounds Com.BH-B and Com.BH-C as a host material in the emitting layer.
Examples 3 to 9 containing a compound represented by the formula (120) as a host material in the emitting layer showed that deterioration in chromaticity was suppressed as compared with Comparative Examples 2 to 4 containing compounds Com.BH-B, Com.BH-C, and Com.BH-A as a host material in the emitting layer.
A compound represented by the formula (2) according to Example 1A has the following structure.
Other compounds used to produce organic EL devices according to Example 1A and Comparative Example 1A have the following structures.
Production 4 of Organic EL Device
An organic EL device was produced and evaluated as described below.
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, manufactured by Geomatec Co., Ltd.) having an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonic-cleaned in isopropyl alcohol for five minutes, and then UV-ozone-cleaned for 30 minutes. The ITO transparent electrode had a thickness of 130 nm.
The cleaned glass substrate having the transparent electrode line was attached to a substrate holder of a vacuum deposition apparatus. First, a compound HI-1 was deposited on a surface on which the transparent electrode line was formed and covered the transparent electrode, thus forming a hole injecting layer (HI) with a thickness of 5 nm.
After the formation of the hole injecting layer, the compound HT-1 was deposited to form a first hole transporting layer (HT) with a thickness of 80 nm.
After the formation of the first hole transporting layer, a compound EBL-1 was deposited to form a second hole transporting layer (also referred to as an electron blocking layer) (EBL) with a thickness of 10 nm.
A compound BH-1A (host material (BH)) and a compound BD-1 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD-1 accounted for 4% by mass, thus forming an emitting layer with a thickness of 25 nm.
A compound HBL-1 was deposited on the emitting layer to form a first electron transporting layer (also referred to as a hole blocking layer) (HBL) with a thickness of 10 nm.
A compound BH-3 was deposited on the first electron transporting layer to form a second electron transporting layer (ET) with a thickness of 15 nm.
LiF was deposited on the second electron transporting layer to form an electron injecting layer with a thickness of 1 nm.
Metal Al was deposited on the electron injecting layer to form a cathode with a thickness of 50 nm.
A device arrangement of an organic EL device in Example 1A is roughly shown as follows.
ITO (130)/HI-1 (5)/HT-1 (80)/EBL-1 (10)/BH-1A:BD-1 (25, 96%:4%)/HBL-1 (10)/BH-3 (15)/LiF (1)/Al (50)
The numerals in parentheses indicate the film thicknesses (unit: nm).
The numerals (96%:4%) represented by percentage in the same parentheses indicate a ratio (% by mass) of the host material (the compound BH-1A) to the compound BD-1 in the emitting layer. Similar notations apply to the description below.
An organic EL device according to Comparative Example 1A was produced in the same manner as in Example 1A except that the compound BH-1A in the emitting layer in Example 1A was replaced with the compound listed in Table 4.
Evaluation 4 of Organic EL Device
The organic EL devices produced in Example 1A and Comparative Example 1A were evaluated as described below. Table 4 shows the evaluation results.
External Quantum Efficiency EQE
Voltage was applied on the organic EL devices so that a current density was 10 mA/cm2, where spectral radiance spectrum was measured by a spectroradiometer (CS-2000 manufactured by Konica Minolta, Inc.). The external quantum efficiency EQE (unit: %) was calculated based on the obtained spectral-radiance spectra, assuming that the spectra was provided under a Lambertian radiation.
Main Peak Wavelength λp while Driving Device
Voltage was applied on the organic EL devices so that a current density was 10 mA/cm2, where spectral radiance spectrum was measured by a spectroradiometer (CS-2000 manufactured by Konica Minolta, Inc.). The main peak wavelength λp (unit: nm) was calculated from the obtained spectral radiance spectrum.
Table 4 shows that the organic EL device according to Example 1A containing the compound BH-1A as a host material in the emitting layer emitted light with a higher luminous efficiency than the organic EL device according to Comparative Example 1A containing the compound Com.BH-A as a host material in the emitting layer.
Preparation of Toluene Solution
The compound BD-1 was dissolved in toluene at a concentration of 4.9×10−6 mol/L to prepare a toluene solution of the compound BD-1.
Measurement of Fluorescent Main Peak Wavelength (FL-Peak)
A fluorescence spectrum measuring apparatus (fluorescence spectrophotometer F-7000 (manufactured by Hitachi High-Tech Science Corporation)) was used to measure a fluorescent main peak wavelength when the toluene solution of the compound BD-1 was excited at 390 nm.
The compound BD-1 had a fluorescent main peak wavelength at 442 nm.
Compound
Compounds represented by the formula (1) or (3) according to Examples 2A to 8A have the following structures.
Other compounds used to produce organic EL devices according to Examples 2A to 8A have the following structures.
Production 5 of Organic EL Device
An organic EL device was produced and evaluated as described below.
A glass substrate (size: 25 mm×75 mm×1.1 mm thick, manufactured by Geomatec Co., Ltd.) having an ITO (Indium Tin Oxide) transparent electrode (anode) was ultrasonic-cleaned in isopropyl alcohol for five minutes, and then UV-ozone-cleaned for 30 minutes. The ITO transparent electrode had a thickness of 130 nm.
The cleaned glass substrate having the transparent electrode line was attached to a substrate holder of a vacuum deposition apparatus. First, a compound HA1 was deposited on a surface on which the transparent electrode line was formed and covered the transparent electrode, thus forming a hole injecting layer (HI) with a thickness of 5 nm.
After the formation of the hole injecting layer, the compound HT1 was deposited to form a first hole transporting layer (HT) with a thickness of 80 nm.
After the formation of the first hole transporting layer, a compound HT2 was deposited to form a second hole transporting layer (also referred to as an electron blocking layer) (EBL) with a thickness of 10 nm.
A compound BH1-11 (first host material (BH)) and a compound BD1 (dopant material (BD)) were co-deposited on the second hole transporting layer such that the ratio of the compound BD1 accounted for 2% by mass, thus forming a first emitting layer with a thickness of 5 nm.
A compound BH2 (second host material (BH)) and the compound BD1 (dopant material (BD)) were co-deposited on the first emitting layer such that the ratio of the compound BD1 accounted for 2% by mass, thus forming a second emitting layer with a thickness of 20 nm.
A compound ET1 was deposited on the second emitting layer to form a first electron transporting layer (also referred to as a hole blocking layer) (HBL) with a thickness of 10 nm.
A compound ET2 was deposited on the first electron transporting layer to form a second electron transporting layer (ET) with a thickness of 15 nm.
LiF was deposited on the second electron transporting layer to form an electron injecting layer with a thickness of 1 nm.
Metal Al was deposited on the electron injecting layer to form a cathode with a thickness of 80 nm.
A device arrangement of an organic EL device in Example 2A is roughly shown as follows.
ITO (130)/HA1 (5)/HT1 (80)/HT2 (10)/BH1-11:BD1 (5, 98%:2%)/BH2:BD1 (20, 98%:2%)/ET1 (10)/ET2 (15)/LiF (1)/Al (80)
Organic EL devices according to Examples 3A to 8A and Comparative Examples 2A to 4A were produced in the same manner as in Example 2A except that the compound BH1-11 in the emitting layer in Example 2A was replaced with the compounds listed in Table 5.
Evaluation 5 of Organic EL Device
The organic EL devices produced in Examples 2A to 7A and Comparative Examples 2A and 3A were evaluated as described below. For the organic EL devices produced in Example 8A and Comparative Example 4A, only CIE1931 chromaticity was measured. Table 5 shows the evaluation results.
External Quantum Efficiency EQE
Voltage was applied on the organic EL devices so that a current density was 10 mA/cm2, where spectral radiance spectrum was measured by a spectroradiometer (CS-2000 manufactured by Konica Minolta, Inc.). The external quantum efficiency EQE (unit: %) was calculated based on the obtained spectral-radiance spectra, assuming that the spectra was provided under a Lambertian radiation.
Life LT95
Voltage was applied on the resultant organic EL devices so that a current density was 50 mA/cm2, where a time (LT95 (unit: hr)) elapsed before a luminance intensity was reduced to 95% of the initial luminance intensity was measured.
Drive Voltage
The voltage (unit: V) when electric current was applied between the anode and the cathode so that the current density was 10 mA/cm2 was measured.
Table 5 shows that Examples 3A to 8A containing a compound represented by the formula (1) or (3) as a host material in the emitting layer emitted light with a higher luminous efficiency than Comparative Examples 2A and 3A containing compounds Com.BH-B and Com.BH-C as a host material in the emitting layer.
Examples 3A to 9A containing a compound represented by the formula (1) or (3) as a host material in the emitting layer showed that deterioration in chromaticity was suppressed as compared with Comparative Examples 2A to 4A containing compounds Com.BH-B, Com.BH-C, and Com.BH-A as a host material in the emitting layer.
1, 1A organic EL device, 2 substrate, 3 anode, 4 cathode, 5 emitting layer, 51 first emitting layer, 52 second emitting layer, 6 hole injecting layer, 7 hole transporting layer, 8 electron transporting layer, 9 electron injecting layer, 10, 10A organic layer.
| Number | Date | Country | Kind |
|---|---|---|---|
| 2019-213374 | Nov 2019 | JP | national |
| 2019-239596 | Dec 2019 | JP | national |
| 2019-239821 | Dec 2019 | JP | national |
| 2019-239883 | Dec 2019 | JP | national |
| 2019-239910 | Dec 2019 | JP | national |
| 2019-239923 | Dec 2019 | JP | national |
| 2019-239931 | Dec 2019 | JP | national |
| 2019-239937 | Dec 2019 | JP | national |
| 2020-023551 | Feb 2020 | JP | national |
| 2020-072968 | Apr 2020 | JP | national |
| 2020-072969 | Apr 2020 | JP | national |
| Filing Document | Filing Date | Country | Kind |
|---|---|---|---|
| PCT/JP2020/044062 | 11/26/2020 | WO |
